HERBICIDAL URACILS

Title:

HERBICIDAL URACILS

Document Type and Number:

WIPO Patent Application WO/2011/137088

Kind Code:

Abstract:

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, (I) wherein R1, X1, X2, W1, A, W2, R3, W3 and R4 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

Inventors:

HONG WONPYO (US)
SELBY THOMAS PAUL (US)

Application Number:

PCT/US2011/033846

Publication Date:

November 03, 2011

Filing Date:

April 26, 2011

Export Citation:

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Assignee:

DU PONT (US)
HONG WONPYO (US)
SELBY THOMAS PAUL (US)

International Classes:

C07D239/54; A01N43/54; C07D401/12; C07D401/14; C07D403/12; C07D405/12; C07D405/14; C07F7/08

Domestic Patent References:

WO2001077084A1	2001-10-18
WO2002098227A1	2002-12-12
WO2007083090A2	2007-07-26
WO2002098227A1	2002-12-12
WO2003024222A1	2003-03-27
WO1991013546A1	1991-09-19

Foreign References:

EP1430776A1	2004-06-23
EP1430775A1	2004-06-23
EP1430777A1	2004-06-23
US7548072B2	2009-06-16
US7548072B2	2009-06-16
EP1255047A2	2002-11-06
EP1122244A1	2001-08-08
US3060084A	1962-10-23
US4172714A	1979-10-30
US4144050A	1979-03-13
US3920442A	1975-11-18
DE3246493A1	1984-06-20
US5180587A	1993-01-19
US5232701A	1993-08-03
US5208030A	1993-05-04
GB2095558A	1982-10-06
US3299566A	1967-01-24
US3235361A	1966-02-15
US3309192A	1967-03-14
US2891855A	1959-06-23

Other References:

"Comprehensive Heterocyclic Chemistry", 1984, PERGAMON PRESS
"Comprehensive Heterocyclic Chemistry II", 1996, PERGAMON PRESS
T. L. GILCHRIST: "Comprehensive Organic Synthesis", vol. 7, PERGAMON PRESS, pages: 748 - 750
M. TISLER, B. STANOVNIK: "Comprehensive Heterocyclic Chemistry", vol. 3, PERGAMON PRESS, pages: 18 - 20
M. R. GRIMMETT, B. R. T. KEENE: "Advances in Heterocyclic Chemistry", vol. 43, ACADEMIC PRESS, pages: 149 - 161
M. TISLER, B. STANOVNIK: "Advances in Heterocyclic Chemistry", vol. 9, ACADEMIC PRESS, pages: 285 - 291
G. W. H. CHEESEMAN, E. S. G. WERSTIUK: "Advances in Heterocyclic Chemistry", vol. 22, ACADEMIC PRESS, pages: 390 - 392
GREENE, T. W., WUTS, P. G. M.: "Protective Groups in Organic Synthesis", 1991, WILEY
WATKINS ET AL.: "Handbook o/` Insecticide Dust Diluents and Carriers", DORLAND BOOKS
MARSDEN: "Solvents Guide", 1950, INTERSCIENCE
"McCutcheon's Emulsifiers and Detergents", MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
SISELY, WOOD: "Encyclopedia of Surface Active Agents", 1964, CHEMICAL PUBL. CO., INC.
A. S. DAVIDSON, B. MILWIDSKY: "Synthetic Detergents", 1987, JOHN WILEY AND SONS
"McCutcheon ',< Volume 2: Functional Materials", vol. 2, MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48
"Perry's Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57
T. S. WOODS: "Pesticide Chemistry and Bioscience, The Food-Environment Challenge", 1999, THE ROYAL SOCIETY OF CHEMISTRY, article "The Formulator's Toolbox - Product Forms for Modem Agriculture", pages: 120 - 133
KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, INC., pages: 81 - 96
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC PUBLICATIONS
"Developments informulation technology", 2000, PJB PUBLICATIONS
"The Pesticide Manual", 2003, BRITISH CROP PROTECTION COUNCIL
"The BioPesticide Manual", 2001, BRITISH CROP PROTECTION COUNCIL
COLBY, S. R.: "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", WEEDS, vol. 15, no. 1, 1967, pages 20 - 22

Attorney, Agent or Firm:

REHBERG, Edward, F. (Legal Patent Records Center4417 Lancaster Pik, Wilmington Delaware, US)

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Claims:

CLAIMS

What is claimed is:

1. A compound selected from Formula 1 N-oxides and salts thereof,

wherein

R¹ is H, amino or C1-C3 alkyl;

X¹ is H or halogen;

X² is halogen, cyano, amino, nitro, -CF₃ or -C(=S)NH₂;

W¹ is O or S;

A is a phenyl, pyridinyl or pyrimidinyl ring, the ring optionally substituted with up to 4 substituents independently selected from R²;

W² is O, S or N(R⁹);

each R² is independently halogen, cyano, Ci-C^, alkyl, Ci-C^, haloalkyl, Ci-C^, alkoxy or C1-C6 haloalkoxy;

R³ is C1-C3 alkylene substituted with at least one R⁵; or

R³ is -C(=0)-;

W³ is O or S;

R⁴ is H, -OR⁶, -SR⁶, -NR⁷R⁸ or -O M+;

M⁺ is an agriculturally suitable alkali metal cation or ammonium cation;

each R⁵ is independently halogen, cyano, hydroxy, Ci-C^, haloalkyl, Ci-C^, alkoxy,

C1-C6 haloalkoxy, C^-C6 alkylthio, C^-C6 alkylamino, C₂-Cg dialkylamino or C2-C6 alkoxycarbonyl;

R⁶ is H, C_rC₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₆ haloalkyl, C₂-C₆

haloalkenyl, C3-C6 haloalkynyl, C₂-C6 alkoxyalkyl, C3-Cg alkoxycarbonylalkyl, C_rC₆ alkylamino, C₂-C₈ dialkylamino, -N=C(R¹⁰)(Rⁿ), C₃-C₁₀ dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C₂-Cg alkylthioalkyl, C₂-Cg alkylsulfinylalkyl, C₂-Cg alkylsulfonylalkyl, C₂-C6 cyanoalkyl, C3-C10 trialkylsilyl, C4-C 1 ^ trialkylsilyl(alkyl), C5-C^₂ trialkylsilyl(alkenyl), C5-C^₂ trialkylsilyl(alkynyl), C5"Ci₂ trialkylsilyl(alkoxyalkyl), C₂-Cg alkylcarbonylamino, C₂-C6 haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl, C3-Cg alkylcarbonylalkyl, C3-Cg alkenyloxyalkyl, C3-Cg alkenyloxycarbonylalkyl, C3-Cg

haloalkenyloxyalkyl, C₂-C6 alkylaminoalkyl, C3-Cg dialkylaminoalkyl, C₂-C6 aminocarbonylalkyl, C3~Cg alkylaminoalkylcarbonylalkyl or C3-Cg

dialkylaminocarbonylalkyl; or

R⁶ is G^A, -(CR¹²R¹³)_qTG^A, G^B or -(CR¹⁴R¹⁵)_UTG^B; or

R⁵ and R⁶ are taken together as Ci -C3 alkylene to form, including the atoms to which said R⁵ and R⁶ are attached, a 4- to 7-membered ring, said ring optionally substituted with up to two substituents selected from halogen, Ci-C₆ alkyl or Ci-Cfr haloalkyl;

each q and u is independently an integer selected from 1 through 4;

each T is independently a direct bond, -0-, -S- or -N(R¹⁸)-;

G^A is phenyl or benzyl; or a 5- or 6-membered heteroaromatic ring, each phenyl, benzyl or heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R¹⁶ on carbon ring members and R¹⁷ on nitrogen ring members;

G^B is a 3- to 7-membered nonaromatic or partially aromatic carbocyclic ring, said ring optionally including ring members selected from the group consisting of -N(R¹⁷)-, -N=N-, -C(=0)-, -O- and -S-, said ring optionally substituted with up to 4 substituents selected from R¹⁶;

R⁷ is H, C_rC₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₃-C₈

alkoxycarbonylalkyl, i-C^ alkoxy or C2~Cg dialkylaminosulfonyl; or a phenyl ring or benzyl, each optionally substituted with up to five substituents selected from C1-C3 alkyl, -CF₃ and C1-C3 alkoxy on ring members;

R⁸ is H or C_rC₃ alkyl; or

a pair of R⁷ and R⁸ attached to the same nitrogen atom are taken together with the

nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 2 N, the ring optionally substituted with up to 4 substituents independently selected from halogen, cyano, Ci -C3 alkyl and C1-C3 alkoxy on carbon atom ring members and C1-C3 alkyl on nitrogen atom ring members;

R⁹ is H or C_rC₃ alkyl;

R¹⁰ and R^{1 1} are each independently H or C1-C3 alkyl;

each R¹², R¹³, R¹⁴ and R¹⁵ is independently H or C_rC₃ alkyl; or

one R¹² and one R¹³ are taken together as an oxygen atom to form, with the carbon atom to which said one R¹² and one R¹³ are attached, a carbonyl moiety;

one R¹⁴ and one R¹⁵ are taken together as an oxygen atom to form, with the carbon atom to which said one R¹² and one R¹³ are attached, a carbonyl moiety;

R¹⁶ is halogen, C 1 -C3 alkyl, -CF₃ or C1 -C3 alkoxy;

each R¹⁷ is H or C1-C3 alkyl; and R¹⁸ is H or C_rC₃ alkyl.

2. The compound of Claim 1 wherein

R¹ is amino or C1-C3 alkyl;

X¹ is halogen;

X² is halogen, cyano or -CF₃;

W¹ is O;

W² is O, S, N(H) or N(CH₃);

A is a phenyl, pyridinyl or pyrimidinyl ring selected from A-1 through A-20

A A-6 A-7 A-8

A-17 A-18 A-19 A-20 n is 0 to 3; R² is halogen, Ci~C₆ alkyl or Ci~C₆ alkoxy;

R³ is Ci-C₂ alkylene substituted with at least one R⁵; or

R³ is -C(=0)-;

W³ is O;

R⁴ is -OR⁶, -SR⁶, -NR⁷R⁸ or -O M+;

M⁺ is an agriculturally suitable alkali metal cation selected from sodium or potassium; each R⁵ is halogen, C1-C3 alkoxy, Ci -C3 haloalkoxy, Ci -C3 alkylthio or C₂-C6

alkoxycarbonyl;

R⁶ is H, C_rC₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₆ haloalkyl, C₂-C₆

haloalkenyl, C3-C6 haloalkynyl, C₂-C6 alkoxyalkyl, C3-Cg alkoxycarbonylalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C₂-Cg alkylthioalkyl, C₂-C6 cyanoalkyl, C3-C10 trialkylsilyl, C₂-Cg alkylcarbonylamino, C₂-C6

haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl or C3-Cg alkylcarbonylalkyl; or

R⁶ is G^A, -(CR¹²R¹ )_qTG^A, G^B or -(CR¹⁴R¹⁵)_UTG^B; or

R⁵ and R⁶ are taken together to form a rin selected from D-l

D-l

R* is selected from C1-C3 alkyl; and

p is 0 or 1.

3. The compound of Claim 2 wherein

R¹ is C_rC₃ alkyl;

X¹ is F or CI;

X² is halogen or cyano;

W² is O, S or N(H);

A is selected from A-1 , A-2, A-3, A-4, A-5, A-6, A-7, A-12, A- 13, A- 14, A- 15, A- 19 and A-20;

n is 0 to 2;

R² is halogen, C1-C3 alkyl or methoxy;

R³ is C_j-C₂ alkylene substituted with one R⁵;

R⁴ is -OR⁶ or -SR⁶;

R⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; and

R⁶ is H, C_rC₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₆ haloalkyl, C₂-C₆

haloalkenyl, C3-C6 haloalkynyl, C₂-C6 alkoxyalkyl, C3-Cg alkoxycarbonylalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C₂-C6 cyanoalkyl; or R⁶ is G^A, -(CR¹²R¹³)_qTG^A, G^B or -(CR¹⁴R¹⁵)_UTG^B.

4. The compound of Claim 3 wherein

R¹ is methyl or ethyl;

X¹ is F;

X² is CI or F;

W² is O or S;

A is selected from A-l , A-2, A-4 and A-15;

R² is halogen, Ci~C₆ alkyl or Ci~C₆ alkoxy;

R³ is Ci-C₂ alkylene substituted with at least one R⁵;

R⁴ is -OR⁶;

R⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio;

R⁶ is H, C_rC₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkyl, C₂-C₆ alkoxyalkyl, C₃-C₈ alkoxycarbonylalkyl, C3-C10 alkoxyalkoxyalkyl or C₂-C6 cyanoalkyl; G^A is phenyl optionally substituted with up to 1 substituent selected from R¹⁶; or G^A is B-51

B-51 q is 1 ;

r is 0;

B is selected from C-2, C-3, C-4 and C-8

C-2 C-3 C-4 C-8 u is 0 or 1 ;

m is 0; and

each T is a direct bond.

5. A compound of Claim 4 wherein

R¹ is methyl;

X² is CI;

W² is O;

A is selected from A-l , A-2 and A-4;

n is 0; R⁵ is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy;

R⁶ is H, CH₃, CH₂CH₃, CH₂CH₂CH₃, CH(CH₃)₂, CH₂CH₂CH₂CH₃, CH₂CH(CH₃)₂, CH₂CH₂CH(CH₃)₂, CH₂CF₃, CH₂CH₂CH₂C1, CH₂CF₂CH₃, CH₂CH₂CH₂F, CH₂CH₂CH₂CF₃, CH₂CH₂Br, CH₂OCH₃, CH₂OCH₂CH₃, CH₂CH₂OCH₃, CH₂CH₂OCH₂CH₃, CH₂C(=0)OCH₃, CH₂C(=0)OCH₂CH₃>

CH₂OCH₂CH₂OMe or CH₂CH₂CN;

G^B is selected from C-2, C-3 and C-4; and

u is 0.

6. A compound of Claim 5 wherein

X² is CI;

A is A-l ;

R⁵ is ethoxy or methoxy;

R⁶ is H, CH₃, CH₂CH₃, CH₂CH₂CH₃, CH₂CF₃, CH₂CH₂CH₂F, CH₂OCH₃,

CH₂OCH₂CH₃, CH₂CH₂OCH₃, CH₂CH₂OCH₂CH₃, CH₂OCH₂CH₂OMe or CH₂CH₂CN;

G^B is C-l ;

u is 1 ;

R¹⁴ is H,

R¹⁵ is H;

R¹⁶ is CH₃; and

R¹⁶ is attached at the 1 -position.

7. A compound of Claim 1 wherein

R¹ is methyl;

X¹ is F;

X² is CI;

W¹ is O;

A is A-l ;

W² is O;

R³ is Ci alkylene substituted with one R⁵;

R⁴ is -OR⁶;

R⁵ is ethoxy or methoxy; and

R⁶ is H, CH₃, CH₂CH₃, CH₂CF₃, CH₂CH₂CH₂F, CH₂CH₂OCH₃ or

CH₂CH₂OCH₂CH₃ or CH₂OCH₂CH₂OMe.

8. A compound of Claim 1 selected from the group consisting of

methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate,

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate,

methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -3 -methoxypropanoate,

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-fluoroacetate,

2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetic acid,

2- ethoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate,

3- fluoropropyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate,

2,2,2-trifluoroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate,

2-methoxy-2-oxoethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate,

2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetic acid,

2-methoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate,

cyolohexyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyaceate,

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -3 -fluoropropanoate,

methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]-5 -fluorophenoxy] -2-methoxyacetate, cyclopentyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate,

2-ethoxy-2-oxoethyl 2-[2-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate, cyclopropylmethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate,

2-chloroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate, propyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate,

butyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate,

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]-4-fluorophenoxy]-2-methoxyacetate, butyl 2-[5-chloro-2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-

1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy] -2-methoxyacetate and

2- cyanoethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-

1 (2H)-pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate .

9. A compound of Claim 8 selected from the group consisting of

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetate,

2,2,2-trifluoroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate,

3- fluoropropyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate, 2-ethoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-

1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy] -2-methoxyacetate and

2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetic acid.

10. A herbicidal composition comprising a compound of Claim 1 and at least one additional herbicide or herbcicide safener.

1 1. A herbicidal composition comprising a compound of Claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

12. A herbicidal composition comprising a compound of Claim 1 , at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

13. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.

14. A method for pre-plant burndown comprising the steps of

(a) contacting a residually effective amount of a compound of Claim 1 with undesired vegetation and its growing medium; and

(b) planting desired vegetation in said growing medium

characterized by providing preemergent control of undesired vegetation without causing injury to said desired vegetation.

Description:

TITLE

HERBICIDAL URACILS

FIELD OF THE INVENTION

This invention relates to certain herbicidal uracils, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

SUMMARY OF THE INVENTION

This invention is directed to a compound of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

R ¹ is H, amino or C1-C3 alkyl;

X ¹ is H or halogen;

X ² is halogen, cyano, amino, nitro, -CF ₃ or -C(=S)NH ₂;

W ¹ is O or S;

A is a phenyl, pyridinyl or pyrimidinyl ring, the ring optionally substituted with up to 4 substituents independently selected from R ²;

W ² is O, S or N(R ⁹);

each R ² is independently halogen, cyano, C^-Cg alkyl, C^-Cg haloalkyl, C^-Cg alkoxy or C^-Cg haloalkoxy;

R ³ is C1-C3 alkylene substituted with at least one R ⁵; or R ³ is -C(=0)-;

W ³ is O or S;

R ⁴ is H, -OR ⁶, -SR ⁶, -NR ⁷R ⁸ or -O M+;

M ⁺ is an agriculturally suitable alkali metal cation or ammonium cation;

each R ⁵ is independently halogen, cyano, hydroxy, C _j-Cg haloalkyl, C _j-Cg alkoxy,

C^-Cg haloalkoxy, C^-Cg alkylthio, C^-Cg alkylamino, C ₂-Cg dialkylamino or C ₂-C ₆ alkoxycarbonyl;

R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₃-C ₆ alkynyl, C ₂-C ₆ haloalkyl, C ₂-C ₆

haloalkenyl, C3-C6 haloalkynyl, C ₂-Cg alkoxyalkyl, C3-Cg alkoxycarbonylalkyl, C _rC ₆ alkylamino, C ₂-C ₈ dialkylamino, -N=C(R ¹⁰)(R ⁿ), C ₃-C ₁₀ dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C ₂-Cg alkylthioalkyl, C ₂-Cg alkylsulfinylalkyl, C ₂-Cg alkylsulfonylalkyl, C ₂-C ₆ cyanoalkyl, C ₃-C ₁₀ trialkylsilyl, C ₄-Cn trialkylsilyl(alkyl), C5-C^ ₂ trialkylsilyl(alkenyl), C5-C^ ₂ trialkylsilyl(alkynyl), C5"Ci ₂ trialkylsilyl(alkoxyalkyl), C ₂-Cg alkylcarbonylamino, C ₂-Cg

haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl, C3-Cg alkylcarbonylalkyl, C3-Cg alkenyloxyalkyl, C3-Cg alkenyloxycarbonylalkyl, C3-Cg

haloalkenyloxyalkyl, C ₂-Cg alkylaminoalkyl, C3-Cg dialkylaminoalkyl, C ₂-Cg aminocarbonylalkyl, C3-Cg alkylaminoalkylcarbonylalkyl or C3-Cg

dialkylaminocarbonylalkyl; or

R ⁶ is G ^A, -(CR ¹²R ¹³) _qTG ^A, G ^B or -(CR ¹⁴R ¹⁵) _UTG ^B; or

R ⁵ and R ⁶ are taken together as C1-C3 alkylene to form, including the atoms to which said R ⁵ and R ⁶ are attached, a 4- to 7-membered ring, said ring optionally substituted with up to two substituents selected from halogen, C _j-Cg alkyl or C _j-Cg haloalkyl;

each q and u is independently an integer selected from 1 through 4;

each T is independently a direct bond, -0-, -S- or -N(R ¹⁸)-;

G ^A is phenyl or benzyl; or a 5- or 6-membered heteroaromatic ring, each phenyl, benzyl or heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R ¹⁶ on carbon ring members and R ¹⁷ on nitrogen ring members;

G ^B is a 3- to 7-membered nonaromatic or partially aromatic carbocyclic ring, said ring optionally including ring members selected from the group consisting of -N(R ¹⁷)-, -N=N-, -C(=0)-, -O- and -S-, said ring optionally substituted with up to 4 substituents selected from R ¹⁶; or

R ⁷ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C ₃-C ₈ cycloalkyl, C ₃-C ₈

alkoxycarbonylalkyl, C^-Cg alkoxy or C ₂-Cg dialkylaminosulfonyl; or a phenyl ring or benzyl, each optionally substituted with up to five substituents selected from C1-C3 alkyl, -CF ₃ and C1-C3 alkoxy on ring members; R ⁸ is H or C _rC ₃ alkyl; or

a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the

nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 2 N, the ring optionally substituted with up to 4 substituents independently selected from halogen, cyano, Ci-C ₃ alkyl and Ci -C3 alkoxy on carbon atom ring members and Ci -C3 alkyl on nitrogen atom ring members;

R ⁹ is H or C _rC ₃ alkyl;

R ¹⁰ and R ^{1 1} are each independently H or C _}-C ₃ alkyl;

each R ¹², R ¹³, R ¹⁴ and R ¹⁵ is independently H or C _rC ₃ alkyl; or

one R ¹² and one R ¹³ are taken together as an oxygen atom to form, with the carbon

atom to which said one R ¹² and one R ¹³ are attached, a carbonyl moiety;

one R ¹⁴ and one R ¹⁵ are taken together as an oxygen atom to form, with the carbon

atom to which said one R ¹² and one R ¹³ are attached, a carbonyl moiety;

R ¹⁶ is halogen, C 1-C3 alkyl, -CF ₃ or C _j-C ₃ alkoxy;

each R ¹⁷ is H or C^-C ₃ alkyl; and

R ¹⁸ is H or C _rC ₃ alkyl.

More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one additional herbicide or herbcicide safener. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein). This invention is also directed to a method for pre -plant burndown.

DETAILS OF THE INVENTION

As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains", "containing," "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method, that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The transitional phrase "consisting of excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase "consisting essentially of is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of occupies a middle ground between "comprising" and "consisting of.

Where applicants have defined an invention or a portion thereof with an open-ended term such as "comprising," it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms "consisting essentially of or "consisting of."

Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to herein, the term "seedling", used either alone or in a combination of words means a young plant developing from the embryo of a seed.

As referred to herein, the term "broadleaf used either alone or in words such as "broadleaf weed" means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.

As used herein, the term "alkylating agent" refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as a halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term "alkylating" does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R ⁴ and R ⁵.

In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkylene" denotes a straight-chain or branched alkanediyl. Examples of "alkylene" include -CH , -CH ₂CH , -CH(CH ₃)-, -CH ₂CH ₂CH , -CH ₂CH(CH ₃)-.

"Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH ₃OCH ₂, CH ₃OCH ₂CH ₂, CH ₃CH ₂OCH ₂, CH ₃CH ₂CH ₂CH ₂OCH ₂ and CH ₃CH ₂OCH ₂CH ₂. "Dialkoxyalkyl" denotes two independent alkoxy groups substituted on the same or different carbon of said alkyl group. Examples of "dialkoxyalkyl" include (CH ₃0) ₂CH and CH ₃CH ₂0(CH ₃0)CH. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylamino", "dialkylamino" and the like, are defined analogously to the above examples. The term "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH ₃SCH ₂, CH ₃SCH ₂CH ₂, CH ₃CH ₂SCH ₂, CH ₃CH ₂CH ₂CH ₂SCH ₂ and CH ₃CH ₂SCH ₂CH ₂. The term "alkylsulfmylalkyl" denotes alkylsulfmyl substitution on alkyl. Examples of "alkylsulfmylalkyl" include CH ₃S(=0)CH ₂, CH ₃S(=0)CH ₂CH ₂, CH ₃CH ₂S(0)CH ₂, CH ₃CH ₂CH ₂CH ₂S(=0)CH ₂ and CH ₃CH ₂S(=0)CH ₂CH ₂. The term "alkylsulfonylalkyl" denotes alkylsulfonyl substitution on alkyl. Examples of "alkylsulfonylalkyl" include CH ₃S(0) ₂CH ₂, CH ₃S(0) ₂CH ₂CH ₂, CH ₃CH ₂S(0) ₂CH ₂, CH ₃CH ₂CH ₂CH ₂S(0) ₂CH ₂ and CH ₃CH ₂S(0) ₂CH ₂CH ₂.

Examples of "alkoxycarbonyl" include CH ₃OC(=0)-, CH ₃CH ₂OC(=0)-, CH ₃CH ₂CH ₂OC(=0)-, (CH ₃) ₂CHOC(=0)- and the different butoxy- or pentoxycarbonyl isomers. "Alkoxyalkoxyalkyl" denotes at least one straight-chain or branched alkoxy moiety bonded to a straight-chain or branched alkoxyalkyl moiety. Examples of "alkoxyalkoxyalkyl" include CH ₃OCH ₂OCH ₂-, CH ₃CH ₂OCH(CH ₃)OCH ₂- and (CH ₃0) ₂CHOCH ₂-. The term "alkenyloxyalkyl" denotes an alkenyloxy moiety bonded through an alkyl group. Examples of "alkenyloxyalkyl" include CH ₂=CHCH ₂OCH ₂-, CH ₃CH=CHCH ₂OCH ₂- and CH ₂=CHCH ₂OCH ₂CH ₂-. "Alkylcarbonyl" denotes a straight-chain or branched alkyl moiety bonded to a C(=0) moiety. Examples of "alkylcarbonyl" include CH ₃C(=0)-, CH ₃CH ₂CH ₂C(=0)- and (CH ₃) ₂CHC(=0)-. The term "alkenyloxycarbonylalkyl" denotes an alkenyloxy group bonded through a carbonyl alkyl group. Examples of "alkenyloxyalkylcarbonylalkyl" include CH ₂=CHCH ₂C(=0)CH ₂-, CH ₃CH=CHCH ₂C(=0)CH ₂- and CH ₂=CHCH ₂C(=0)CH ₂CH ₂-. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl. The term "alkylaminoalkyl" denotes a straight-chain or branched alkyl moiety bonded to a nitrogen atom of amino(straight-chain or branched)alkyl moiety. Examples of "alkylaminoalkyl" include CH ₃NHCH , (CH ₃) ₂CHNHCH ₂- and CH ₃NHCH(CH ₃)-. The term "dialkylaminoalkyl" denotes two straight-chain or branched alkyl moieties bonded to a nitrogen atom of amino(straight-chain or branched)alkyl moiety. Examples of "dialkylaminoalkyl" include (CH ₃) ₂NCH , (CH ₃) ₂CN(CH ₃)CH ₂- and CH ₃N(CH ₃)CH(CH ₃)-. The term "aminocarbonylalkyl" denotes an amino group bonded to a carbonylalkyl moiety. Examples of "aminocarbonylalkyl" include H ₂NC(=0)CH ₂- and H ₂NC(=0)CH(CH ₃)-. The term "dialkylaminocarbonylalkyl" denotes a dialkylamino group bonded to the C(=0) moiety of a carbonylalkyl group. Examples of a "dialkylaminocarbonylalkyl" group include (CH ₃) ₂NC(=0)CH ₂- and (CH ₃CH ₂) ₂NC(=0)CH(CH ₃)-. The term "alkylaminoalkylcarbonylalkyl" denotes a straight-chain or branched alkylaminoalkyl group bonded to the C(=0) moiety of a carbonylalkyl group. Examples of "alkylaminoalkylcarbonylalkyl" include

CH ₃NHCH ₂C(=0)CH ₂- and CH ₃CH ₂NHCH ₂C(=0)CH ₂-. The term "alkylcarbonylamino" denotes a straight-chain or branched alkyl group bonded to a C(=0)NH- moiety. Examples of "alkylcarbonylamino" include CH ₃C(=0)NH-, CH ₃CH ₂CH ₂C(=0)NH- and (CH ₃) ₂CHC(=0)NH-.

The term "halogen", either alone or in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" include F ₃C-, C1CH ₂-, CF ₃CH ₂- and CF ₃CC1 ₂-. The terms "haloalkoxy", "haloalkenyl", "haloalkynyl", "haloalkenyloxyalkyl", "haloakoxyalkyl", "haloalkoxycarbonylalkyl" and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkoxy" include CF ₃0-, CC1 ₃CH ₂0-, HCF ₂CH ₂CH ₂0- and CF ₃CH ₂0-. Examples of "haloalkenyl" include (C1) ₂C=CHCH ₂- and CF ₃CH ₂CH=CHCH ₂-. Examples of "haloalkynyl" include HC≡CCHC1-, CF ₃C≡C-, CC1 ₃C≡C- and FCH ₂C≡CCH ₂-. Examples of "halocycloalkyl" include 2-chlorocyclopropyl, 2-fluorocyclobutyl, 3-bromocyclopentyl and 4-chorocyclohexyl." The term "halocycloalkenyl" denotes halogen substitution on cycloalkenyl. "Cyanoalkyl" denotes an alkyl group substituted with one or more cyano group. Examples of "cyanoalkyl" include NCCH ₂-, (NC) ₂CH-, NCCH ₂CH ₂- and CH ₃CH(CN)CH ₂-. The term "dialkylaminosulfonyl" denotes two independent straight-chain or branched alkyl moieties bonded to a nitrogen atom of aminosulfonyl. Examples of "dialkylaminosulfonyl" include (CH ₃) ₂NS(0) ₂-, (CH ₃CH ₂CH ₂)(CH ₃)NS(0) ₂-, ((CH ₃) ₂CH)(CH ₃)NS(0) ₂- and ((CH ₃) ₂CH) ₂NS(0) ₂-. The term "alkoxycarbonylalkyl" denotes alkoxycarbonyl substitution on a straight-chain or branched alkyl. Examples of "alkoxycarbonylalkyl" include CH ₃OC(=0)CH ₂-, CH ₃CH ₂OC(=0)CH ₂CH ₂-, CH ₃CH ₂CH ₂OC(=0)CH ₂-, (CH ₃) ₂CHOC(=0)CH ₂-, CH ₃OC(=0)CH(CH ₃)- and the different butoxy- or pentoxycarbonyl isomers.

"Trialkylsilyl" includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom. Examples include as trimethylsilyl, triethylsilyl and tert- butyldimethylsilyl. When this term is followed by a group in paranthases (i.e. trialkylsilyl(alkyl), trialkylsilyl(alkenyl) trialkylsilyl(alkoxy alkyl) or trialkylsilyl(alkynyl)) the parenthetical group links the trialkylsilyl group to the described variable. The total number of carbon atoms preceeding the term trialkylsilyl includes the carbon atoms in both the trialkylsilyl moiety and the parenthetical group.

The total number of carbon atoms in a substituent group is indicated by the "C _j-Cj" prefix where i and j are numbers from 1 to 10. For example, C1-C4 alkylamino designates methylamino through butylamino; C ₂ alkoxyalkyl designates CH ₃OCH ₂-; C ₃ alkoxyalkyl designates, for example, CH ₃CH(OCH ₃)-, CH ₃OCH ₂CH ₂- or CH ₃CH ₂OCH ₂-; and C ₄ alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH ₃CH ₂CH ₂OCH ₂- and CH ₃CH ₂OCH ₂CH ₂-.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R ²) _n, n is 0, 1, 2, 3 or 4. When a group contains a substituent which can be hydrogen, for example R ¹ or X ¹, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R ²) _n wherein n may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be "not substituted" or "unsubstituted", then hydrogen atoms are attached to take up any free valency.

Unless otherwise indicated, a "ring" as a component of Formula 1 (e.g., substituent A) is carbocyclic or heterocyclic. The term "ring member" refers to an atom or other moiety (e.g., O, S or N) forming the backbone of a ring.

The terms "carbocyclic ring", "carbocycle" or "carbocyclic ring system" denote a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Huckel's rule, then said ring is also called an "aromatic ring". "Saturated carbocyclic" refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

The terms "heterocyclic ring", "heterocycle" or "heterocyclic ring system" denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 2 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Huckel's rule, then said ring is also called a "heteroaromatic ring" or "aromatic heterocyclic ring". Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

The term "optionally substituted" in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated. The term "optionally substituted" is used interchangeably with the phrase "substituted or unsubstituted" or with the term "(un)substituted". Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

Where R ³ is defined in the Summary of the Invention as C1-C ₃ alkylene substituted with at least one R ⁵, the C1-C ₃ alkylene connects the W ² and -C(=W ³)R ⁴ moieties in Forumla 1. When R ³ is C^ alkylene substituted with at least one R ⁵, the resulting compound is either Formula l ^la or l ^lb below wherein W ² is attached to A in Formula 1).

jla _jib

When R ³ is C2 alkylene substituted with at least one R ⁵, the C2 alkylene can be either straight-chain or branched. The R ⁵ substitutent can be attached to either (or both) of the two available carbon atoms. The resulting structure is a compound of either Forumulae l ^2a or l ^2b below (where W ² is attached to A in a compound of Formula 1). The remaining positions making up the C2 alkylene are substituted with hydrogen or any additional R ⁵ substituents, up to the total maximum number of R ⁵ substitutents allowed as defined in the Summary of the Invention.

j 2;i , 2b

When R ³ is C3 alkylene substituted with at least one R ⁵, the R ⁵ substituent can be attached to any of the carbon atoms of the C3 alkylene. The resulting structure is either a compound of Forumulae l ^3a, l ^3b, l ^3c or l ^3d below (where W ² is attached to A in Formula 1). The remaining carbon atoms making up the C3 alkylene are substituted with hydrogen or any additional R ⁵ substituents, up to the maximum number of R ⁵ substituents allowed as defined in the Summar of the Invention.

, 3a , 3b , 3c , 3d

Where R ⁴ is defined in the Summary of the Invention particularly as -O M ⁺, the 0 ^~ in this term refers to the anion of oxygen. For example, when W ³ is S or O, the resulting thiocarboxylic acid or carboxylic acid (i.e. when R ⁴ is OH) can deprotonate to form an anion. Therefore, M ⁺ as defined in the Summary of the Invention can be any agriculturally suitable alkali metal cation or ammonium cation which is associated with the 0 ^~ anion. Agriculturally suitiable alkali metal cations include lithium (Li ⁺), sodium (Na ⁺) or potassium (K ⁺). Agriculturally suitable ammonium cations include trimethylammonium ((C ^^N ^"1"), triethylammonium ((CH ₃CH ₂) ₃N ⁺) and tributylammonium ((CH3CH2CH ₂CFl2)3N ⁺).

As described in the Summary of the Invention, one R ¹² and one R ¹³ can be together as an oxygen atom to form, with the carbon atom to which said one R ¹² and one R ¹³ are attached, a carbonyl moiety. For example when R ⁴ is -OR ⁶ or -SR ⁶; R ⁶ is -(CR ¹²R ¹³) _qTG ^A; and q is 1, 2, 3 or 4, only one (CR ¹²R ¹³) can be taken together to make a carbonyl. As a specific example, compound 73 in Index Table A is a compound wherein R ⁴ is -OR ⁶, R ⁶ is -(CR ¹²R ¹³)qTG ^A, G ^A is a phenyl ring; T is a direct bond; q is 2; one -(CR ¹²R ¹³) moiety is -CH2 and the second -(CR ¹²R ¹³) moiety is a carbonyl (i.e. one R ¹² and one R ¹³ are taken together as an oxygen atom to form, with the carbon atom to which said one R ¹² and one R ¹³ are attached, a carbonyl moiety). As described in the Summary of the Invention, one R ¹ and one R ¹⁵ can be taken together as an oxygen atom to form, with the carbon atom to which said one R ¹² and one R ¹³ are attached, a carbonyl moiety. For example when R ⁴ is -OR ⁶ or -SR ⁶; R ⁶ is -(CR ¹⁴R ¹⁵) _UTG ^B; and u is 1, 2, 3 or 4, only one (CR ¹⁴R ¹⁵) can be taken together to make a carbonyl. When substituent A is a phenyl, pyridinyl or pyrimidinyl ring it may be attached to the remainder of Formula 1 though any available carbon atom, unless otherwise described. As noted above, A can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. An example of phenyl optionally substituted with up to four substituents is the ring illustrated as A-l through A-3 in Exhibit 1, wherein (R ²) _n is as defined in the Summary of the Invention for R ² (i.e. halogen or cyano) and n is an integer from 0 to 4.

As noted above, A can also be a pyridinyl or pyrimidnyl ring, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention as shown in Exhibit 1 wherein the bond projecting to the left is connected to W ¹ and the bond projecting to the right is connected to W ² in Formula 1; and n is 0 to 4. Examples of a phenyl ring optionally substituted with up to four substituents include the rings A-l through A-3 illustrated in Exhibit 1 wherein (R ²) _n is any substituent as defined in the Summary of the Invention for (R ²) (i.e. halogen or cyano etc.) and n is an integer from 0 to 4, limited by the number of available positions on each A group. Examples of a pyridinyl or pyrimidinyl ring optionally substituted with up to four substituents include the rings A-4 through A-20 illustrated in Exhibit 1 wherein (R ²) _n is any substituent as defined in the Summary of the Invention for (R ²) (i.e. halogen or cyano etc.) and n is an integer from 0 to 4, limited by the number of available positions on each A group. As A- 14 through A-20 have only two available positions, for these A groups n is limited to the integers 0, 1 or 2, and n being 0 means that the A group is unsubstituted and a hydrogen is present at the position indicated by (R ²) _n.

Exhibit 1

A-l A-2 A-3 A-

A-9 A-10 A-l l A-12

A-13 A-14 A-15 A-16

A-17 A-18 A-19 A-20

As noted above, a pair of R ⁷ and R ⁸ attached to the same nitrogen atom can be taken together with the nitrogen atom to form a 3 - to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 2 N, the ring optionally substituted with up to 4 substituents independently selected from halogen, cyano, C1-C3 alkyl and C1-C3 alkoxy on carbon atom ring members and C1-C3 alkyl on nitrogen atom ring members. In this definition the ring members selected from up to 2 O, up to 2 S and up to 2 N atom are optional, because the number of heteroatom ring members may be zero. The ring is optionally substituted with up to 4 substituents independently independently selected from halogen, cyano, C1-C3 alkyl and C1-C3 alkoxy on carbon atom ring members and C1-C3 alkyl on nitrogen atom ring members. These optional substituents (when present) are attached to available carbon and nitrogen atom ring members in the portion of the ring provided by R ⁷ and R ⁸.

As defined in the Summary of the Invention, G ^A can be a 5- or 6-membered heteroaromatic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered heteroaromatic ring optionally substituted with from one or more substituents include the rings B-l through B-60 illustrated in Exhibit 2 wherein R ^v is any substituent as defined in the Summary of the Invention for R ¹⁶ on carbon ring members or R ¹⁷ on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each B group. As B-29, B-30, B-32, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-42, B-43, B-45, B-46 and B-47 have only one available position, for these B groups r is limited to the integers 0 or 1 , and r being 0 means that the B group is unsubstituted and a hydrogen is present at the position indicated by (R ^v) _r.

Exhibit 2

B-l B-2 B-3 B-4 B-5

B-6 B-7 B-8 B-9 B-10

B-l l B-12 B-13 B-14 B-15

B-16 B-17 B-18 B-19 -20

B-21 B-22 B-23 B-24 B-25

B-26 B-27 B-28 B-29 B-30

B-31 B-32 B-33 B-34 B-35

B-41 B-42 B-43 B-44 B-45

B-56 B-57 B-58 B-59 B-60

As defined in the Summary of the Invention, G ^B can be a 3- to 7-membered nonaromatic or partially aromatic carbocyclic ring, the ring optionally includes ring members selected from the group consisting of -N(R ¹⁷)-, -N=N-, -C(=0)-, -O- and -S-. The ring is optionally substituted with up to 4 substituents selected from R ¹⁶ (wherein R ¹⁶ is defined in the Summary of the Invention) on carbon ring members and R ¹⁷ (wherein R ¹⁷ is defined in the Summary of the Invention) on nitrogen ring members when the ring includes -N(R ¹⁷)-. Examples include C-1 through C-32 as shown in Exhibit 3 below.

Exhibit 3

C-9 C-10 C-l l C-12

C-13 C-14 C-15 C-16

C-17 C-18 C-19 C-20

C-21 C-22 C-23 C-24

C-25 C-26 C-27 C-28

C-29 C-30 C-31 C-32

As described in the Summary of the Invention, R ⁵ and R ⁶ are taken together as C1-C3 alkylene to form, including the atoms to which said R ⁵ and R ⁶ are attached, a 4- to 7-membered ring, said ring optionally substituted with up to two substituents selected from halogen, Ci~C ₆ alkyl or Ci~C ₆ haloalkyl. Therefore, the 4- to 7-membered ring, includes the ring members to which they are attached (i.e. including -R ³C(=W ³)R ⁴ specifically when R ⁴ is -OR ⁶ or -SR ⁶). The resulting 4- to 7-membered ring is optionally substituted with up to two substituents selected from halogen, Ci-C ₆ alkyl or Ci~C ₆ haloalkyl. Examples of R ⁵ and R ⁶ taken together as C1-C3 alkylene to form a 4- to 7-membered ring include D-l through D-15 as shown in Exhibit 4 below wherein R* is selected from halogen, i-C^ alkyl or Ci-Cfr haloalkyl and p is 0 to 2 as described above and wherein the bond projecting to the left is attached to the remainder of Formula 1 through W ².

Exhibit 4

D-l D-2 D-3 D-4

D-5 D-6 D-7 D-8

D-9 D-10 D-12

D-13 D-14 D-15

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form. For example, when R ³ is C^ alkylene substituted by one R ⁵, then Formula 1 possesses a chiral center at the carbon atom to which R ⁵ is bonded. The two enantiomers are depicted as Formula 1' and Formula 1" with the chiral center identified with an asterisk *).

Molecular depictions drawn herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the narrow end of the wedge is attached to the atom further away from the viewer. Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified.

This invention comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1' and 1". In addition, this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula 1. Also included are the essentially pure enantiomers of compounds of Formula 1, for example, Formula 1' and Formula 1".

When enantiomerically enriched, one enantiomer is present in greater amounts than the other, and the extent of enrichment can be defined by an expression of enantiomeric excess ("ee"), which is defined as (2χ-1)· 100 %, where x is the mole fraction of the dominant enantiomer in the mixture (e.g., an ee of 20 % corresponds to a 60:40 ratio of enantiomers).

Preferably the compositions of this invention have at least a 50 % enantiomeric excess; more preferably at least a 75 % enantiomeric excess; still more preferably at least a 90 % enantiomeric excess; and the most preferably at least a 94 % enantiomeric excess of the more active isomer. Of particular note are enantiomerically pure embodiments of the more active isomer.

Compounds of Formula 1 can comprise additional chiral centers. For example, substituents and other molecular constituents such as R ², R ⁶ and R ⁷ may themselves contain chiral centers. This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers.

Compounds of this invention can exist as one or more conformational isomers due to restricted rotation about the amide bond (e.g., when R ⁶ is -N=C(R ¹⁰)(R ^{1 1})) in Formula 1. This invention comprises mixtures of conformational isomers. In addition, this invention includes compounds that are enriched in one conformer relative to others.

Compounds of Formula 1 typically exist in more than one form, and thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof. Embodiments of the present invention as described in the Summary of the Invention include those below. In the following Embodiments, Formula 1 includes N-oxides and salts thereof, and reference to "a compound of Formula 1" includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.

Embodiment 1. A compound of Formula 1 wherein R ¹ is amino or C 1-C3 alkyl.

Embodiment 2. A compound of Embodiment 1 wherein R ¹ is Ci -C3 alkyl.

Embodiment 3. A compound of Embodiment 2 wherein R ¹ is methyl or ethyl.

Embodiment 4. A compound of Embodiment 3 wherein R ¹ is methyl.

Embodiment 5. A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X ¹ is H.

Embodiment 6. A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X ¹ is halogen.

Embodiment 7. A compound of Embodiment 6 wherein X ¹ is F or CI.

Embodiment 8. A compound of Embodiment 7 wherein X ¹ is F.

Embodiment 9. A compound of Formula 1 or any one of Embodiments 1 through 8 wherein X ² is halogen, cyano, amino, nitro or -CF ₃.

Embodiment 10. A compound of Formula 1 or any one of Embodiments 1 through 9 wherein X ² is halogen, cyano or -CF ₃.

Embodiment 11. A compound of Embodiment 10 wherein X ² is halogen or cyano. Embodiment 12. A compound of Embodiment 11 wherein X ² is CI, F or cyano.

Embodiment 13. A compound of Embodiment 12 wherein X ² is CI or F.

Embodiment 14. A compound of Embodiment 13 wherein X ² is CI.

Embodiment 15. A compound of Embodiment 9 wherein X ² is halogen or nitro.

Embodiment 16. A compound of Embodiment 15 wherein X ² is CI, F or nitro.

Embodiment 17. A compound of Formula 1 or any one of Embodiments 1 through 16 wherein W ¹ is S.

Embodiment 18. A compound of Formula 1 or any one of Embodiments 1 through 16 wherein W ¹ is O.

Embodiment 19. A compound of Formula 1 or any one of Embodiments 1 through 18 wherein W ² is O, S, N(H) or N(CH ₃).

Embodiment 20. A compound of Embodiment 19 wherein W ² is O, S or N(H).

Embodiment 21. A compound of Embodiment 20 wherein W ² is O or S.

Embodiment 22. A compound of Embodiment 20 wherein W ² is S.

Embodiment 23. A compound of Embodiment 20 wherein W ² is O.

Embodiment 24. A compound of Formula 1 or any one of Embodiments 1 through 23 wherein A is a phenyl, pyridinyl or pyrimidinyl ring selected from

A-3 A-4

A-17 A-18 A-19 A-20 wherein the bond projecting to the left is connected to W ¹ and the bond projecting to the right is connected to W ² in Formula 1; and n is 0 to 3.

Embodiment 25. A compound of Embodiment 24 wherein A is selected from A-1, A-2,

A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14, A-15, A-19 and A-20.

Embodiment 26. A compound of Embodiment 25 wherein A is selected from A-1, A-2,

A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14 and A-15.

Embodiment 27. A compound of Embodiment 26 wherein A is selected from A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-14 and A-15. Embodiment 28. A compound of Embodiment 27 wherein A is selected from A-1, A-2,

A-3, A-4, A-7 and A-15.

Embodiment 29. A compound of Embodiment 28 wherein A is selected from A-1, A-2,

A-4 and A-15.

Embodiment 30. A compound of Embodiment 29 wherein A is selected from A-1, A-2 and A-4.

Embodiment 31. A compound of Embodiment 30 wherein A is A- 1.

Embodiment 32. A compound of Embodiment 30 wherein A is A-2.

Embodiment 33. A compound of Embodiment 30 wherein A is A-4.

Embodiment 34. A compound of any one of Embodiments 24 through 33 wherein n is 0 to 2.

Embodiment 35. A compound of Embodiment 34 wherein n is 1.

Embodiment 36. A compound of Embodiment 34 wherein n is 0.

Embodiment 37. A compound of Embodiment 35 wherein R ² is attached at the 4- or 5 -position.

Embodiment 38. A compound of Embodiment 37 wherein R ² is attached at the

4- position.

Embodiment 39. A compound of Embodiment 37 wherein R ² is attached at the

5 - position.

Embodiment 40. A compound of Formula 1 or any one of Embodiments 1 through 39 wherein R ² is halogen, Ci~C ₆ alkyl or Ci~C ₆ alkoxy.

Embodiment 41. A compound of Embodiment 40 wherein R ² is halogen, C1-C3 alkyl or methoxy.

Embodiment 42. A compound of Embodiment 41 wherein R ² is halogen.

Embodiment 43. A compound of Embodiment 42 wherein R ² is F or CI.

Embodiment 44. A compound of Embodiment 43 wherein R ² is F.

Embodiment 45. A compound of Embodiment 41 wherein R ² is methyl or methoxy. Embodiment 46. A compound of Embodiment 45 wherein R ² is methyl.

Embodiment 47. A compound of Embodiment 41 wherein R ² is F or methyl.

Embodiment 48. A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R ³ is Ci -C3 alkylene substituted with two R ⁵.

Embodiment 49. A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R ³ is Ci -C3 alkylene substituted with one R ⁵.

Embodiment 50. A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R ³ is C1-C2 alkylene substituted with at least one R ⁵.

Embodiment 51. A compound of Embodiment 50 wherein R ³ is C1-C2 alkylene

substituted with two R ⁵. Embodiment 52. A compound of Embodiment 50 wherein R ³ is C1-C2 alkylene substituted with one R ⁵.

Embodiment 53. A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R ³ is C alkylene substituted with at least one R ⁵.

Embodiment 54. A compound of Embodiment 53 wherein R ³ is C alkylene substituted with two R ⁵.

Embodiment 55. A compound of Embodiment 53 wherein R ³ is C alkylene substituted with one R ⁵.

Embodiment 56. A compound of Formula 1 or any one of Embodiments 1 through 48,

50, 51 , 53 and 54 wherein R ³ is C^ alkylene substituted with two R ⁵.

Embodiment 57. A compound of Formula 1 or any one of Embodiments 1 through 47,

49, 50, 52, 53 and 55 wherein R ³ is C^ alkylene substituted with one R ⁵.

Embodiment 58. A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R ³ is -C(=0)-.

Embodiment 59. A compound of Formula 1 or any one of Embodiments 1 through 58 wherein W ³ is S.

Embodiment 60. A compound of Formula 1 or any one of Embodiments 1 through 58 wherein W ³ is O.

Embodiment 61. A compound of Formula 1 or any one of Embodiments 1 through 60 wherein R ⁴ is -OR ⁶, -SR ⁶, -NR ⁷R ⁸ or -O M+.

Embodiment 62. A compound of Embodiment 61 wherein R ⁴ is -OR ⁶, -NR ⁷R ⁸ or

-0-M+.

Embodiment 63. A compound of Embodiment 62 wherein R ⁴ is -NH(OCH ₃),

-NH(CH ₃), -N(CH ₃) ₂ or -NH(Ph).

Embodiment 64. A compound of Embodiment 63 wherein R ⁴ is -NH(OCH ₃) or

-NH(CH ₃).

Embodiment 65. A compound of Embodiment 64 wherein R ⁴ is -NH(CH ₃).

Embodiment 66. A compound of Embodiment 65 wherein R ⁴ is -NH(OCH ₃).

Embodiment 67. A compound of Embodiment 61 wherein R ⁴ is -OR ⁶ or -0 ^~M ⁺.

Embodiment 68. A compound of Embodiment 67 wherein R ⁴ is -0 ^~M ⁺.

Embodiment 69. A compound of Embodiment 68 wherein M ⁺ is an agriculturally

suitable alkali metal cation selected from sodium and potassium.

Embodiment 70. A compound of Embodiment 69 wherein M ⁺ is sodium.

Embodiment 71. A compound of Embodiment 69 wherein M ⁺ is potassium.

Embodiment 72. A compound of Embodiment 69 wherein M ⁺ is an agriculturally

suitable ammonium cation selected from trimethylammonium,

triethylammonium or tributylammonium.

Embodiment 73. A compound of Embodiment 72 wherein M ⁺ is triethylammonium. Embodiment 74. A compound of Embodiment 72 wherein M ⁺ is trimethylammonium. Embodiment 75. A compound of Embodiment 62 or 67 wherein R ⁴ is -OR ⁶.

Embodiment 76. A compound of Formula 1 or any one of Embodiments 1 through 75 wherein each R ⁵ is independently halogen, cyano, hydroxy, -CF ₃, Ci~C ₆ alkoxy,

C^-C6 haloalkoxy, Ci-C^ alkylthio or C2-C6 alkoxy carbonyl.

Embodiment 77. A compound of Embodiment 76 wherein each R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C2-C4 alkoxycarbonyl.

Embodiment 78. A compound of Embodiment 77 wherein each R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio.

Embodiment 79. A compound of Embodiment 78 wherein each R ⁵ is halogen, C1-C3 alkoxy or C1-C3 haloalkoxy.

Embodiment 80. A compound of Embodiment 79 wherein R ⁵ is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy.

Embodiment 81. A compound of Embodiment 80 wherein R ⁵ is fluoro.

Embodiment 82. A compound of Embodiment 80 wherein R ⁵ is C1-C2 alkoxy.

Embodiment 83. A compound of Embodiment 82 wherein R ⁵ is ethoxy.

Embodiment 84. A compound of Embodiment 82 wherein R ⁵ is methoxy.

Embodiment 85. A compound of Formula 1 or any one of Embodiments 1 through 84 wherein R ⁵ and R ⁶ are taken together as C1-C3 alkylene to form, including the atoms to which said R ⁵ and R ⁶ are attached, a 5- to 6-membered ring, said ring optionally substituted with up to two substituents selected from halogen, Ci~C ₆ alkyl or C^-C6 haloalkyl;.

Embodiment 86. A compound of Embodiment 85 wherein R ⁵ and R ⁶ are taken together to form a rin selected from

D-l D-2 D-3 D-4 wherein R* is selected from halogen, C1-C3 alkyl or -C^ haloalkyl; and p is 0, 1 or 2.

Embodiment 87. A compound of Embodiment 86 wherein p is 0 or 1.

Embodiment 88. A compound of Embodiment 87 wherein R ⁵ and R ⁶ are taken together to form ring D-l .

Embodiment 89. A compound of Embodiment 88 wherein R* is methyl attached to the

5-position of D-l; and p is 1.

Embodiment 90. A compound of Embodiment 88 wherein and p is 0. Embodiment 91. A compound of Formula 1 or any one of Embodiments 1 through 84 wherein R ⁶ is H, Ci~C ₆ alkyl, C ₂-C ₆ alkenyl, C ₃-C ₆ alkynyl, C ₂-C ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C ₃-C ₆ haloalkynyl, C ₂-C ₆ alkoxyalkyl, C ₃-C ₈

alkoxycarbonylalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C ₂-Cg alkylthioalkyl, C ₂-C ₆ cyanoalkyl, C ₃-C ₁₀ trialkylsilyl, C ₂-C ₈

alkylcarbonylamino, C ₂-C6 haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl or C3-Cg alkylcarbonylalkyl.

Embodiment 92. A compound of Embodiment 91 wherein R ⁶ is H, i-C^ alkyl, C ₂-C6 alkenyl, C3-C6 alkynyl, C ₂-C6 haloalkyl, C ₂-C6 haloalkenyl, C3-C6 haloalkynyl, C ₂-C ₆ alkoxyalkyl, C ₃-C ₈ alkoxycarbonylalkyl, C ₃-C ₁₀ dialkoxyalkyl, C ₃-C ₁₀ alkoxyalkoxyalkyl or C ₂-C6 cyanoalkyl.

Embodiment 93. A compound of Embodiment 92 wherein R ⁶ is H, Ci~C ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C6 haloalkyl, C ₂-C6 alkoxyalkyl, C3-Cg alkoxycarbonylalkyl C3-C10 alkoxyalkoxyalkyl or C ₂-C6 cyanoalkyl.

Embodiment 94. A compound of Embodiment 93 wherein R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CH ₂CH ₃, CH(CH ₃) ₂, CH ₂CH ₂CH ₂CH ₃, CH ₂CH(CH ₃) ₂,

CH ₂CH ₂CH(CH ₃) ₂, CH ₂CF ₃, CH ₂CH ₂CH ₂C1, CH ₂CF ₂CH ₃, CH ₂CH ₂CH ₂F, CH ₂CH ₂CH ₂CF ₃, CH ₂CH ₂Br, CH ₂OCH ₃, CH ₂OCH ₂CH ₃, CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃, CH ₂C(=0)OCH ₃, CH ₂C(=0)OCH ₂CH ₃,

CH ₂OCH ₂CH ₂OMe or CH ₂CH ₂CN.

Embodiment 95. A compound of Embodiment 94 wherein R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CH ₂CH ₃, CH ₂CF ₃, CH ₂CH ₂CH ₂F, CH ₂OCH ₃, CH ₂OCH ₂CH ₃,

CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃ or CH ₂CH ₂CN.

Embodiment 96. A compound of Embodiment 95 wherein R ⁶ is H, CH ₃, CH ₂CH ₃,

CH ₂CH ₂CH ₃, CH ₂CF ₃, CH ₂CH ₂CH ₂F, CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃ or CH ₂OCH ₂CH ₂OMe.

Embodiment 97. A compound of Embodiment 96 wherein R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CF ₃, CH ₂CH ₂CH ₂F, CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃ or

CH ₂OCH ₂CH ₂OMe.

Embodiment 98. A compound of Embodiment 97 wherein R ⁶ is CH ₃.

Embodiment 99. A compound of Embodiment 97 wherein R ⁶ is CH ₂CH ₃.

Embodiment 100. A compound of Embodiment 97 wherein R ⁶ is CH ₂CH ₂CH ₂F.

Embodiment 101. A compound of Embodiment 97 wherein R ⁶ is CH ₂CH ₂OCH ₃.

Embodiment 102. A compound of Embodiment 97 wherein R ⁶ is CH ₂CH ₂OCH ₂CH ₃.

Embodiment 102A. A compound of Embodiment 97 wherein R ⁶ is CH ₂OCH ₂CH ₂OMe.

Embodiment 103. A compound of Embodiment 97 wherein R ⁶ is H.

Embodiment 104. A compound of Formula 1 or any one of Embodiments 1 through 97 wherein R ⁶ is other than H. Embodiment 105. A compound of Formula 1 or any one of Embodiments 1 through 62 or 67 or 75 through 84 wherein R ⁶ is G ^B or -(CR ¹⁴R ¹⁵) _UTG ^B.

Embodiment 106. A com ound of Embodiment 105 wherein G ^B is selected from

C-1 C-2 C-3 C-4

C-5 C-6 C-7 C-8 wherein m is an integer selected from 0 to 3.

Embodiment 107. A compound of Embodiment 106 wherein u is 0 or 1; and m is 0. Embodiment 108. A compound of Embodiment 107 wherein R ⁶ is G ^B; and G ^B is selected from C-2, C-3, C-4 and C-8; and u is 0.

Embodiment 109. A compound of Embodiment 108 wherein R ⁶ is G ^B; G ^B is selected from C-2, C-3 and C-4; and m is 0.

Embodiment 110. A compound of Embodiment 106 wherein u is 1; and T is a direct bond.

Embodiment 111. A compound of Embodiment 110 wherein R ⁶ is -(CR ¹⁴R ¹⁵) _UTG ^B and G ^B is selected from C-1 and C-2.

Embodiment 112. A compound of Embodiment 1 1 1 wherein T is a direct bond.

Embodiment 113. A compound of Embodiment 1 12 wherein G ^B is C-1; u is 1; and R ¹⁶ is attached at the 1 -position.

Embodiment 114. A compound of Embodiment 113 wherein G ^B is C-1; and m is 0. Embodiment 115. A compound of Embodiment 110 wherein G ^B is selected from C-6 and C-7; and m is 0.

Embodiment 116. A compound of Embodiment 1 15 wherein G ^B is C-6.

Embodiment 117. A compound of Embodiment 1 15 wherein G ^B is C-7.

Embodiment 118. A compound of Formula 1 or any one of Embodiments 1 through 62 or 67 or 75 through 84 wherein R ⁶ is G ^A or -(CR ¹²R ¹³) _qTG ^A.

Embodiment 119. A compound of Embodiment 118 wherein R ⁶ is G ^A; and G ^A is phenyl optionally substituted with up to 1 substituent selected from R ¹⁶.

Embodiment 120. A compound of Embodiment 118 wherein R ⁶ is -(CR ¹²R ¹³) _qTG ^A; and G ^A is selected from

B-50 B-51

Embodiment 121. A compound of Embodiment 120 wherein T is a direct bond; q is 0 or 1 ; and r is 0.

Embodiment 122. A compound of Embodiment 121 whereien G ^A is B-51 ; and q is 1. Embodiment 123. A compound of Formula 1 or any one of Embodiments 1 through 122 wherein R ⁷ when taken alone (i.e. not taken together with R ⁸) is H, i-C^ alkyl,

C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C ₃-C ₈ cycloalkyl, C ₃-C ₈ alkoxycarbonylalkyl,

C^-C6 alkoxy or C ₂-C ₈ dialkylaminosulfonyl.

Embodiment 124. A compound Embodiment 123 wherein R ⁷ when taken alone is H,

Ci-Cfr alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C ₃-C ₈ cycloalkyl or C ₃-C ₈ alkoxycarbonylalkyl .

Embodiment 125. A compound of Embodiment 124 wherein R ⁷ when taken alone is H, methyl, ethyl, -CH ₂C=CH ₂, -CH ₂C≡CH, cyclohexyl or C ₃-C ₈

alkoxycarbonylalkyl .

Embodiment 126. A compound of Embodiment 125 wherein R ⁷ when taken alone is H, methyl, -CH ₂CH ₂C(=0)OCH ₃ or -CH ₂CH ₂C(=0)OCH ₂CH ₃.

Embodiment 127. A compound of Embodiment 126 wherein R ⁷ when taken alone is methyl.

Embodiment 128. A compound of Formula 1 or any one of Embodiments 1 through 127 wherein R ⁸ when taken alone (i.e. not taken together with R ⁷) is H, methyl or ethyl.

Embodiment 129. A compound of Embodiment 128 wherein R ⁸ when taken alone is H. Embodiment 130. A compound of Embodiment 128 wherein R ⁸ when taken alone is methyl.

Embodiment 131. A compound of Formula 1 or any one of Embodiments 1 through 122 wherein a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 2 heteroatoms selected from up to 2 O and up to 2 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, Ci -C3 alkyl and Ci -C3 alkoxy on carbon atom ring members and methyl on nitrogen atom ring members. Embodiment 132. A compound of Embodiment 131 wherein a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 1 heteroatom selected from 1 O and 1 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, Ci-C ₃ alkyl and C1-C3 alkoxy on carbon atom ring members and methyl on nitrogen atom ring members.

Embodiment 133. A compound of Embodiment 132 wherein a pair of R ⁷ and R ⁸

attached to the same nitrogen atom are taken together with the nitrogen atom to form a 6-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 1 heteroatom selected from 1 O, the ring optionally substituted with up to 1 substituent independently selected from halogen and C1-C3 alkyl.

Embodiment 134. A compound of Embodiment 133 wherein a pair of R ⁷ and R ⁸

attached to the same nitrogen atom are taken together with the nitrogen atom to form a 5-membered heterocyclic ring containing ring members selected from carbon atoms, the ring optionally substituted with up to 1 substituent independently selected from halogen and Ci-C^ alkyl.

Embodiment 135. A compound of Formula 1 or any one of Embodiments 1 through 134 wherein R ⁹ is H or methyl.

Embodiment 136. A compound Embodiment 135 wherein R ⁹ is methyl.

Embodiment 137. A compound Embodiment 136 wherein R ⁹ is H.

Embodiment 138. A compound of Formula 1 or any one of Embodiments 1 through 137 wherein each R ¹², R ¹³, R ¹⁴ and R ¹⁵ is independently H or methyl.

Embodiment 139. A compound of Embodiment 138 wherein each R ¹ and R ¹⁵ is

independently H or methyl.

Embodiment 140. A compound of Embodiment 138 wherein each R ¹², R ¹³, R ¹⁴ and R ¹⁵ is independently H.

Embodiment 141. A compound of Embodiment 140 wherein each R ¹ and R ¹⁵ is

independently H.

Embodiment 142. A compound of Formula 1 or any one of Embodiments 1 through 141 wherein each R ¹⁶ is H, halogen, C1-C3 alkyl or -CF ₃.

Embodiment 143. A compound of Embodiment 142 wherein each R ¹⁶ is H, halogen,

CH ₃ or -CF ₃.

Embodiment 144. A compound of Embodiment 143 wherein each R ¹⁶ is CH ₃.

Embodiments of this invention, including Embodiments 1-144 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compositions comprising the compounds of Formula 1 but also to the compounds of Formula 1, the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1 unless further defined in the Embodiments. In addition, embodiments of this invention, including Embodiments 1-144 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention. Combinations of Embodiments 1-144 are illustrated by:

Embodiment Al . A compound of Formula 1 as described in the Summary of the

Invention wherein

R ¹ is amino or C1-C3 alkyl;

X ¹ is halogen;

X ² is halogen, cyano or -CF ₃;

W ¹ is O;

W ² is O, S, N(H) or N(CH ₃);

A is a phenyl, pyridinyl or pyrimidinyl ring selected from A-l through A-20; n is 0 to 3;

R ² is halogen, Ci~C ₆ alkyl or Ci~C ₆ alkoxy;

R ³ is -C2 alkylene substituted with at least one R ⁵; or

R ³ is -C(=0)-;

W ³ is O;

R ⁴ is -OR ⁶, -SR ⁶, -NR ⁷R ⁸ or -O M+;

M ⁺ is an agriculturally suitable alkali metal cation selected from sodium or potassium;

each R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or

C ₂-C ₆ alkoxycarbonyl;

R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₃-C ₆ alkynyl, C ₂-C ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C3-C6 haloalkynyl, C ₂-C6 alkoxyalkyl, C3-Cg

alkoxycarbonylalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C ₂-C ₈ alkylthioalkyl, C ₂-C ₆ cyanoalkyl, C ₃-C ₁₀ trialkylsilyl, C ₂-C ₈ alkylcarbonylamino, C ₂-C6 haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl or C3-Cg alkylcarbonylalkyl; or

R ⁶ is G ^A, -(CR ¹²R ¹ ) _qTG ^A, G ^B or -(CR ¹⁴R ¹⁵) _UTG ^B; or

R ⁵ and R ⁶ are taken together to form a ring selected from D-1

D-1 Rt is selected from -C3 alkyl; and

p is 0 or 1.

Embodiment A2. A compound of Embodiment Al wherein

R ¹ is C _rC ₃ alkyl;

X ¹ is F or CI;

X ² is halogen or cyano;

W ² is O, S or N(H);

A is selected from A-l , A-2, A-3, A-4, A-5, A-6, A-7, A- 12, A- 13, A- 14,

A- 15, A- 19 and A-20;

n is 0 to 2;

R ² is halogen, C1-C3 alkyl or methoxy;

R ³ is Ci-C ₂ alkylene substituted with one R ⁵;

R ⁴ is -OR ⁶ or -SR ⁶;

R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; and

R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₃-C ₆ alkynyl, C ₂-C ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C3-C6 haloalkynyl, C ₂-C6 alkoxyalkyl, C3-Cg

alkoxycarbonylalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C ₂-C ₆ cyanoalkyl; or

R ⁶ is G ^A, -(CR ¹²R ¹³) _qTG ^A, G ^B or -(CR ¹⁴R ¹⁵) _UTG ^B.

Embodiment A3. A compound of Embodiment A2 wherein

R ¹ is methyl or ethyl;

X ¹ is F;

X ² is CI or F;

W ² is O or S;

A is selected from A-l , A-2, A-4 and A-l 5;

R ² is halogen, Ci~C ₆ alkyl or Ci~C ₆ alkoxy;

R ³ is C ₁-C ₂ alkylene substituted with at least one R ⁵;

R ⁴ is -OR ⁶;

R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio;

R ⁶ is H, Ci-Cfr alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ haloalkyl, C ₂-C ₆ alkoxyalkyl,

C3-Cg alkoxycarbonylalkyl, C3-C10 alkoxyalkoxyalkyl or C ₂-C6 cyanoalkyl;

G ^A is phenyl optionally substituted with up to 1 substituent selected from

R ¹⁶; or

G ^A is B-51 ;

q is 1 ;

r is 0;

G ^B is selected from C-2, C-3, C-4 and C-8; u is 0 or 1 ; and

each T is a direct bond.

Embodiment A4. A compound of Embodiment A3 wherein

R ¹ is methyl;

X ² is CI;

W ² is O;

A is selected from A-l, A-2 and A-4;

n is 0;

R ⁵ is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy;

R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CH ₂CH ₃, CH(CH ₃) ₂, CH ₂CH ₂CH ₂CH ₃,

CH ₂CH(CH ₃) ₂, CH ₂CH ₂CH(CH ₃) ₂, CH ₂CF ₃, CH ₂CH ₂CH ₂C1, CH ₂CF ₂CH ₃, CH ₂CH ₂CH ₂F, CH ₂CH ₂CH ₂CF ₃, CH ₂CH ₂Br,

CH ₂OCH ₃, CH ₂OCH ₂CH ₃, CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃, CH ₂C(=0)OCH ₃, CH ₂C(=0)OCH ₂CH ₃, CH ₂OCH ₂CH ₂OMe or CH ₂CH ₂CN;

G ^B is selected from C-2, C-3 and C-4; and

u is 0.

Embodiment A5. A compound of Embodiment A3 wherein

X ² is CI;

A is selected from A-l;

R ⁵ is ethoxy or methoxy;

R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CH ₂CH ₃, CH ₂CF ₃, CH ₂CH ₂CH ₂F, CH ₂OCH ₃, CH ₂OCH ₂CH ₃, CH ₂CH ₂OCH ₃, CH ₂CH ₂OCH ₂CH ₃, CH ₂OCH ₂CH ₂OMe or CH ₂CH ₂CN;

G ^B is C-l ;

u is 1;

R ¹⁴ is H,

R ¹⁵ is H;

R ¹⁶ is CH ₃; and

R ¹⁶ is attached at the 1 -position.

Embodiment A6. A compound of Formula 1 as described in the Summary of the

Invention or any one of Embodiment Al to A5 wherein

R ¹ is methyl;

X ¹ is F;

X ² is CI;

W ¹ is O;

A is A-l;

W ² is O; R ³ is Ci alkylene substituted with one R ⁵;

R ⁴ is -OR ⁶

R ⁵ is ethoxy or methoxy; and

R ⁶ is H, CH ₃, CH ₂CH ₃, CH ₂CF ₃, CH ₂CH ₂CH ₂F, CH ₂CH ₂OCH ₃ or

CH ₂CH ₂OCH ₂CH ₃ or OCH ₂OCH ₂CH ₂OMe.

Specific embodiments include compounds of Formula 1 selected from the group consisting of:

methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-ethoxyacetate (Compound 4), ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-ethoxyacetate (Compound 2), methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 3), ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate, (Compound 5), methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -3 -methoxypropanoate (Compound 6), ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-fluoroacetate (Compound 1), 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetic acid (Compound 126),

2- ethoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 20),

3- fluoropropyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 24),

2,2,2-trifluoroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate (Compound 55),

2-methoxy-2-oxoethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate (Compound 21),

2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetic acid (Compound 125), 2-methoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound

19), cyolohexyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyaceate (Compound 56),

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-3-fluoropropanoate (Compound 137), methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy] -5 -fluorophenoxy] -2-methoxyacetate (Compound 214),

cyclopentyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 23),

2-ethoxy-2-oxoethyl 2-[2-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate (Compound 22),

cyclopropylmethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate (Compound 18),

2-chloroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound

27),

propyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy] -2-methoxyacetate (Compound 127), butyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy] -2-methoxyacetate (Compound 14), ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy] -4-fluorophenoxy] -2-methoxyacetate (Compound

216),

butyl 2-[5-chloro-2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 21 1) and

2-cyanoethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 53).

ote is a compound of Formula 1 selected from the group consisting of

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 5), 2,2,2-trifluoroethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate (Compound 55),

3-fluoropropyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifiuor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound

24),

2-ethoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate (Compound 20) and

2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl] -4-fluorophenoxy]phenoxy] -2-methoxyacetic acid, (Compound 126).

This invention is also directed to a compound of Formula IP (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

R ¹ is Η, amino or C1-C3 alkyl;

X ¹ is Η or halogen;

X ² is halogen, cyano, amino, nitro, -CF ₃ or -C(=S)NH ₂;

W ¹ is O or S;

A is a phenyl, pyridinyl or pyrimidinyl ring, the ring optionally substituted with up to 4 substituents independently selected from R ²;

W ² is O, S or N(R ⁹);

each R ² is independently halogen, cyano, i~C ₆ alkyl, Ci~C ₆ haloalkyl, Ci~C ₆ alkoxy or Ci-Cft haloalkoxy;

R ³ is C1-C3 alkylene substituted with at least one R ⁵;

W ³ is O or S;

R ⁴ is H, -OR ⁶, -SR ⁶ or -NR ⁷R ⁸;

each R ⁵ is independently halogen, cyano, hydroxy, -CF ₃, Ci~C ₆ alkoxy, i~C ₆

haloalkoxy, Ci-C^ alkylthio, Ci-C^ alkylamino or C2-Cg dialkylamino; R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C _rC ₆ haloalkyl, C ₂-C ₆

haloalkenyl, C -C^ haloalkynyl, C ₂-C6 alkoxyalkyl, C ₃-Cg alkoxycarbonylalkyl, C ₃-C ₈ cycloalkyl, C ₃-C ₈ halocycloalkyl, C ₃-C ₈ halocycloalkenyl, C ₃-C ₁₀ cycloalkenyl, i-C^ alkylamino, C ₂-C ₈ dialkylamino or -N=C(R ¹⁰)(R ^{1 1}); or a phenyl ring or benzyl, each optionally substituted with up to five substituents independently selected from Ci -C3 alkyl, -CF ₃ and Ci -C3 alkoxy on ring members;

R ⁷ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C ₃-C ₈ cycloalkyl, C ₃-C ₈

alkoxycarbonylalkyl, i-C^ alkoxy or C ₂-C ₈ dialkylaminosulfonyl; or a phenyl ring or benzyl, each optionally substituted with up to five substituents selected from C^-C ₃ alkyl, -CF ₃ and C^-C ₃ alkoxy on ring members;

R ⁸ is H or C _rC ₃ alkyl; or

a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the

nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 2 N, the ring optionally substituted with up to 4 substituents independently selected from halogen, cyano, Ci -C3 alkyl and C _j- C ₃ alkoxy on carbon atom ring members and C^-C ₃ alkyl on nitrogen atom ring members;

R ⁹ is H or C _rC ₃ alkyl; and

R ¹⁰ and R ^{1 1} are each independently H or C^-C ₃ alkyl.

Embodiments of the present invention as described in the Summary of the Invention include those below. In the following Embodiments, Formula 1 includes N-oxides and salts thereof, and reference to "a compound of Formula 1" includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.

Embodiment IP. A compound of Formula 1 wherein R ¹ is amino or C^-C ₃ alkyl.

Embodiment 2P. A compound of Embodiment IP wherein R ¹ is C^-C ₃ alkyl.

Embodiment 3P. A compound of Embodiment 2P wherein R ¹ is methyl or ethyl.

Embodiment 4P. A compound of Embodiment 3P wherein R ¹ is methyl.

Embodiment 5P. A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X ¹ is H.

Embodiment 6P. A compound of Formula 1 or any one of Embodiments IP through 4P wherein X ¹ is halogen.

Embodiment 7P. A compound of Embodiment 6P wherein X ¹ is F or CI.

Embodiment 8P. A compound of Embodiment 7P wherein X ¹ is F.

Embodiment 9P. A compound of Formula 1 or any one of Embodiments IP through 8P wherein X ² is halogen, cyano or -CF ₃.

Embodiment 10P. A compound of Embodiment 9P wherein X ² is halogen or cyano. Embodiment 1 IP. A compound of Embodiment 10P wherein X ² is CI, F or cyano. Embodiment 12P. A compound of Embodiment I IP wherein X ² is CI or F.

Embodiment 13P. A compound of Embodiment 12P wherein X ² is CI.

Embodiment 14P. A compound of Formula 1 or any one of Embodiments IP through 13P wherein W ¹ is S.

Embodiment 15P. A compound of Formula 1 or any one of Embodiments IP through

13P wherein W ¹ is O.

Embodiment 16P. A compound of Formula 1 or any one of Embodiments IP through

15P wherein W ² is O, S, N(H) or N(CH ₃).

Embodiment 17P. A compound of Embodiment 16P wherein W ² is O, S or N(H). Embodiment 18P. A compound of Embodiment 17P wherein W ² is O or S.

Embodiment 19P. A compound of Embodiment 18P wherein W ² is S.

Embodiment 20P. A compound of Embodiment 18P wherein W ² is O.

Embodiment 2 IP. A compound of Formula 1 or any one of Embodiments IP through

20P wherein A is phenyl, pyridinyl or a 1 ,3-pyrimidinyl ring selected from A-l

-20

A-l A-2 A-3 A-4

A-5 A-6 A-7 A-8

A-9 A-10 A-l l A-12

A-13 A-14 A-15 A-16

A-17 A-18 A-19 A-20 wherein the bond projecting to the left is connected to W ¹ and the bond projecting to the right is connected to W ² in Formula 1; and n is 0 to 4.

Embodiment 22P. A compound of Embodiment 21P wherein A is selected from A-l,

A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14, A-15, A-19 and A-20. Embodiment 23P. A compound of Embodiment 22P wherein A is selected from A-l,

A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14 and A-15.

Embodiment 24P. A compound of Embodiment 23P wherein A is selected from A-l,

A-3, A-4, A-5, A-6, A-7, A-14 and A-15.

Embodiment 25P. A compound of Embodiment 24P wherein A is selected from A-l,

A-3, A-4, A-7 and A-15.

Embodiment 26P. A compound of Embodiment 25P wherein A is selected from A-l,

A-4 and A-15.

Embodiment 27P. A compound of Embodiment 26P wherein A is selected from A-l and A-4.

Embodiment 28P. A compound of Embodiment 27P wherein A is A-l .

Embodiment 29P. A compound of Embodiment 27P wherein A is A-4.

Embodiment 3 OP. A compound of any one of Embodiments 2 IP through 29P wherein n is 0 to 2.

Embodiment 3 IP. A compound of Embodiment 3 OP wherein n is 0.

Embodiment 32P. A compound of Formula 1 or any one of Embodiments IP through

30P wherein R ² is halogen, Q-C^ alkyl or C _j-C6 alkoxy.

Embodiment 33P. A compound of Embodiment 32P wherein R ² is halogen, -C3 alkyl or methoxy.

Embodiment 34P. A compound of Embodiment 33P wherein R ² is halogen.

Embodiment 35P. A compound of Embodiment 34P wherein R ² is F or CI.

Embodiment 36P. A compound of Embodiment 33P wherein R ² is methyl or methoxy. Embodiment 37P. A compound of Embodiment 36P wherein R ² is methyl.

Embodiment 38P. A compound of Formula 1 or any one of Embodiments IP through

37P wherein R ³ is C1-C2 alkylene substituted with at least one R ⁵.

Embodiment 39P. A compound of Embodiment 38P wherein R ³ is -C2 alkylene substituted one R ⁵.

Embodiment 40P. A compound of Embodiment 38P wherein R ³ is C ₂ alkylene

substituted with at least one R ⁵. Embodiment 4 IP. A compound of Embodiment 38P wherein R ³ is C^ alkylene substituted with at least one R ⁵.

Embodiment 42P. A compound of Embodiment 4 IP wherein R ³ is C^ alkylene

substituted with one R ⁵.

Embodiment 43P. A compound of Formula 1 or any one of Embodiments IP through

42P wherein W ³ is S.

Embodiment 44P. A compound of Formula 1 or any one of Embodiments IP through

42P wherein W ³ is O.

Embodiment 45P A compound of Formula 1 or any one of Embodiments IP through

44P herein R ⁴ is -OR ⁶ or -SR ⁶, -NH ₂, -NH(CH ₃) or -N(CH ₃) ₂.

Embodiment 46P. A compound of Embodiment 45P wherein R ⁴ is-OR ⁶ or -SR ⁶.

Embodiment 47P. A compound of Embodiment 46P wherein R ⁴ is -OR ⁶.

Embodiment 48P. A compound of Formula 1 or any one of Embodiments IP through

47P wherein R ⁵ is halogen, hydroxy, Ci-C^ alkoxy, Ci-C^ haloalkoxy, Ci-C^ alkylthio, Ci -C3 alkylamino or C ₂-C6 dialkylamino.

Embodiment 49P. A compound of Embodiment 48P wherein R ⁵ is halogen, C1-C3 alkoxy, Ci -C3 haloalkoxy or C1-C3 alkylthio.

Embodiment 50P. A compound of Embodiment 49P wherein R ⁵ is Ci -C3 alkoxy or Ci -

C ₃ alkylthio.

Embodiment 5 IP. A compound of Embodiment 5 OP wherein R ⁵ is C 1 -C2 alkoxy or C^- C ₂ alkylthio.

Embodiment 52P. A compound of Embodiment 49P wherein R5 is halogen.

Embodiment 53P. A compound of Embodiment 52P wherein R5 is F.

Embodiment 54P. A compound of Embodiment 5 IP wherein R5 is methylthio.

Embodiment 55P. A compound of Embodiment 5 IP wherein R5 is C 1 -C2 alkoxy.

Embodiment 56P. A compound of Embodiment 55P wherein R5 is ethoxy.

Embodiment 57P. A compound of Embodiment 55P wherein R5 is methoxy.

Embodiment 58P. A compound of Formula 1 or any one of Embodiments 1 through 57 wherein R ⁶ is H, Ci~C ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, Ci~C ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C ₂-C ₆ haloalkynyl, C ₂-C ₆ alkoxyalkyl, C ₃-C ₈ cycloalkyl, C3-Cg halocycloalkyl, C3-Cg halocycloalkenyl or C3-C10 cycloalkenyl.

Embodiment 59P. A compound of Embodiment 58P wherein R ⁶ is H, i-C^ alkyl, C ₂- C ₆ alkenyl, C ₂-C ₆ alkynyl, Ci~C ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C ₂-C ₆ haloalkynyl or C ₂-C6 alkoxyalkyl.

Embodiment 60P. A compound of Embodiment 59P wherein R ⁶ is H, i-C^ alkyl, C ₂- C3 alkenyl, C1-C3 haloalkyl or C ₂-C3 alkoxyalkyl.

Embodiment 61P. A compound of Embodiment 60P wherein R ⁶ is Ci-C^ alkyl. Embodiment 62P. A compound of Embodiment 6 IP wherein R ⁶ is methyl, ethyl, n- propyl, /-propyl or n-butyl.

Embodiment 63P. A compound of Embodiment 62P wherein R ⁶ is methyl or ethyl. Embodiment 64P. A compound of Embodiment 62P wherein R ⁶ is ethyl.

Embodiment 65P. A compound of Embodiment 62P wherein R ⁶ is methyl.

Embodiment 66P. A compound of Formula 1 or any one of Embodiments 1 through 65 wherein R ⁹ is H or methyl.

Embodiment 67P. A compound Embodiment 66P wherein R ⁹ is methyl.

Embodiment 68P. A compound Embodiment 66P wherein R ⁹ is H.

Embodiment 69P. A compound of Formula 1 or any one of Embodiments IP through

68P wherein R ⁷ when taken alone (i.e. not taken together with R ⁸) is H, y-C^ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C ₃-C ₈ cycloalkyl, C ₃-C ₈

alkoxycarbonylalkyl, y-C^ alkoxy or C ₂-C ₈ dialkylaminosulfonyl.

Embodiment 70P. A compound Embodiment 69P wherein R ⁷ when taken alone is H, y-Cfr alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl C ₃-C ₈ cycloalkyl or C ₃-C ₈ alkoxycarbonylalkyl .

Embodiment 7 IP. A compound of Embodiment 70P wherein R ⁷ when taken alone is H, methyl, ethyl, -CH ₂C=CH ₂, -CH ₂CCH, cyclohexyl or C ₃-C ₈

alkoxycarbonylalkyl .

Embodiment 72P. A compound of Embodiment 7 IP wherein R ⁷ when taken alone is H, methyl, -CH ₂CH ₂C(=0)OCH ₃ or -CH ₂CH ₂C(=0)OCH ₂CH ₃.

Embodiment 73P. A compound of Embodiment 72P wherein R ⁷ when taken alone is methyl.

Embodiment 74P. A compound of Formula 1 or any one of Embodiments IP through 73P wherein R ⁸ when taken alone (i.e. not taken together with R ⁷) is H, methyl or ethyl.

Embodiment 75P. A compound of Embodiment 74P wherein R ⁸ when taken alone is H. Embodiment 76P. A compound of Embodiment 74P wherein R ⁸ when taken alone is methyl.

Embodiment 77P. A compound of Formula 1 or any one of Embodiments IP through 76P wherein a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 2 heteroatoms selected from up to 2 O and up to 2 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, C^-C ₃ alkyl and C^-C ₃ alkoxy on carbon atom ring members and methyl on nitrogen atom ring members. Embodiment 78P. A compound of Embodiment 77P wherein a pair of R ⁷ and R ⁸ attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 1 heteroatom selected from 1 O and 1 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, C1-C3 alkyl and Ci -C3 alkoxy on carbon atom ring members and methyl on nitrogen atom ring members.

Embodiment 79P. A compound of Embodiment 78P wherein a pair of R ⁷ and R ⁸

Embodiment 80P. A compound of Embodiment 78P wherein a pair of R ⁷ and R ⁸

Embodiments of this invention, including Embodiments 1P-80P above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compositions comprising the compounds of Formula 1 but also to the compounds of Formula 1, the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1 unless further defined in the Embodiments. In addition, embodiments of this invention, including Embodiments 1-80 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention. Combinations of Embodiments 1-80 are illustrated by:

Embodiment Bl . A compound of the Summary of the Invention wherein

R ¹ is amino or C1-C3 alkyl;

X ¹ is halogen;

X ² is halogen, cyano or -CF ₃;

W ¹ is O;

W ² is O, S, N(H) or N(CH ₃);

A is phenyl, pyridinyl or a 1 ,3-pyrimidinyl ring selected from A-l through

A-20;

n is 0 to 4;

R ² is halogen, Ci~C ₆ alkyl or Ci~C ₆ alkoxy;

R ³ is Ci -C2 alkylene substituted with at least one R ⁵; W ³ is O;

R ⁴ is -OR ⁶ or -SR ⁶, -NH ₂, -NH(CH ₃) or -N(CH ₃) ₂;

R ⁵ is halogen, hydroxy, -C3 alkoxy, C1-C3 haloalkoxy, -C3 alkylthio, C1-C3 alkylamino or C ₂-C6 dialkylamino; and

R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C _rC ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C ₂-C6 haloalkynyl, C ₂-C6 alkoxyalkyl, C3-Cg cycloalkyl, C3-Cg halocycloalkyl, C3-Cg halocycloalkenyl or C3-C10 cycloalkenyl. Embodiment B2. A compound of Embodiment Bl wherein

R ¹ is C _rC ₃ alkyl;

X ¹ is F or CI;

X ² is halogen or cyano;

W ² is O, S or N(H);

A is selected from A-1, A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14, A-15,

A-19 and A-20;

n is 0 to 2;

R ² is halogen, C1-C3 alkyl or methoxy;

R ³ is C ₁-C ₂ alkylene substituted with one R ⁵;

R ⁴ is -OR ⁶ or -SR ⁶;

R ⁵ is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; and R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₆ alkenyl, C ₂-C ₆ alkynyl, C _rC ₆ haloalkyl, C ₂-C ₆ haloalkenyl, C ₂-C6 haloalkynyl or C ₂-C6 alkoxyalkyl.

Embodiment B3. A compound of Embodiment B2 wherein

R ¹ is methyl or ethyl;

X ¹ is F;

X ² is CI, F or cyano;

W ² is O or S;

A is A-1, A-3, A-4, A-5, A-6, A-7, A-14 and A-15;

R ² is halogen;

R ³ is Ci alkylene substituted with one R ⁵;

R ⁴ is -OR ⁶;

R ⁵ is C1-C3 alkoxy or C1-C3 alkylthio; and

R ⁶ is H, C _rC ₆ alkyl, C ₂-C ₃ alkenyl, C _rC ₃ haloalkyl or C ₂-C ₃ alkoxyalkyl. Embodiment B4. A compound of Embodiment B3 wherein

R ¹ is methyl;

X ² is CI or F;

W ² is O;

A is selected from A-1, A-4 and A-15;

n is 0; R ⁵ is Ci -C2 alkoxy or Ci -C2 alkylthio; and

R ⁶ is methyl, ethyl, n-propyl, /-propyl or n-butyl.

Embodiment B5. A compound of Embodiment B4 wherein

X ² is CI;

A is selected from A-l and A-4;

R ⁵ is ethoxy or methoxy; and

R ⁶ is methyl or ethyl.

Specific embodiments include compounds of Formula 1 selected from the group consisting of:

methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetate, ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetate, methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate ;

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate , methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-3-methoxypropano ate, and

ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)- l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-fluoroacetate.

This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of weeds in perennial plantation crops such as sugarcane and citrus.

Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.

This invention is also directed to a method for pre-plant burndown comprising the steps of (a) contacting a residually effective amount of a compound of Formula 1 with undesired vegetation (i.e. weeds) and its growing medium; and (b) planting desired vegetation (i.e. crops) in said growing medium characterized by providing preemergent control of undesired vegetation without causing injury to said desired vegetation.

This method provides control (both postemergent and preemergent) of undesired vegetation (i.e. weeds) in a growing medium intended to be planted with desired vegetation (i.e. crops). Planting of desired vegetation in said growing medium can be accomplished within hours or days of contacting the undesired vegetation and its growing medium with a residually effective amount of a compound of Formula 1. The method is characterized by providing control of undesired vegetation until the desired vegetation establishes a weed- controlling canopy. The method is also characterized by the absence of injury to said desired vegetation. The method requires contacting a residually effective amount of a compound of Formula 1 with undesired vegetation and its growing medium. A "residually effective amount" is the amount contacted to provide both postemergent and preemergent control of undesired vegetation (without causing injury to said desired vegetation) until the desired vegetation provides a weed-controlling canopy. Once formed, a weed controlling canopy intervenes to provide control of undesired vegetation such that a residually effective amount of a compound of Formula 1 is no longer needed. One skilled in the art can easily determine the "residually effective amount" appropriate to control (both postemergent and preemergent) undesired vegetation so as not cause injury to the desired vegetation until the desired vegetation establishes a weed-controlling canopy. The "residually effective amount" will depend on such factors as species of both undesired and desired vegetation, growing medium, weather conditions and the like.

One or more of the following methods and variations as described in Schemes 1-20 can be used to prepare the compounds of Formula 1. The definitions of R ¹, X ¹, X ², W ¹, A, W ², R ², R ³, W ³, R ⁴, R ⁵, R ⁶, R ⁷ or R ⁸ in the compounds of Formulae 1-30 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae la- Id are various subsets of the compounds of Formula 1, and all substituents for Formulae la- Id are as defined above for Formula 1.

As shown in Scheme 1, a compound of Formula la (wherein R ⁴ is other than H) can be prepared by reacting a compound of Formula 2 wherein R ^3a is C1-C3 alkylene and Y ¹ is a leaving group such as chloride, bromide, iodide or an alkylsulfonate (such as mesylate (-OMs) or tosylate (-OTs)) with a compound of Formula 3 in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride. The reaction can be performed in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide. Scheme 1

As shown in Scheme 2, a compound of Formula 2 can be prepared by the reaction of a compound of Formula 4 with halogenating agents such as bromine, sodium bromite, N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) in a solvent such as acetic acid, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or 1,4-dioxane, or a mixture of water with the aforementioned solvents. The reaction can be performed at temperatures ranging from ambient to the boiling point of the solvent.

As shown in Scheme 3, a compound of Formula lb (i.e. a compound of Formula 1 wherein A is A-l, A-2 or A-3) can be prepared by the reaction of a phenol, thiophenol or aniline of Formula 5 with various alkylating agents such as a compound of Formula 7 wherein Y ³ is a leaving group such as chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide. A compound of Formula 7 is commercially available or its preparation is known. Scheme 3

Preparation of a compound of Formula lc (i.e. a compound of Formula 1 wherein A is pyridine or pyrimidine ring A-4 through A-20) can be prepared as shown in Scheme 4. Reaction of a phenol, thiophenol or aniline of Formula 5a with various alkylating agents such as a compound of Formula 7 wherein Y ³ is a leaving group such as chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide can generate a compound of Formula lc. A compound of Formula 7 is commercially available or its preparation is known.

Scheme 4

Preparation of a compound of Formula lc (i.e. a compound of Formula 1 wherein Y ⁴ is in an ortho relationship with a ring nitrogen) can also be prepared as shown in Scheme 5. Reaction of a compound of Formula 9 wherein Y ⁴ is a leaving group such as fluoride, chloride, bromide, iodide or an alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) with a compound of Formula 10 in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide can generate a compound of Formula lc. A compound of Formula 10 is commercially available or its preparation is known. Scheme 5

As shown in Scheme 6, a compound of Formula 9 wherein Y ⁴ is a leaving group such as a halogen can be prepared by reaction of a compound of Formula 11 with halogenating agents such as oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorous pentachloride or phosphorous oxybromide in solvents such as dichloromethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or 1,4-dioxane, or without solvents at temperatures ranging from 0 °C to 150 °C. Alternatively, a compound of Formula 9 can be prepared by reduction followed by halogenation of a compound of Formula 12. Reduction of the nitro group on a compound of Formula 12 can be achieved by treatment with iron powder in acetic acid or by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature. Halogenation of the resulting amine can be achieved by a Sandmeyer reaction by treatment with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) and copper (I) and/or copper (II) halide, hydrofluoric acid pyridine complex or tetrafluoroboric acid in a solvent such as acetonitrile and at temperatures ranging from 0 °C to the reflux temperature of the solvent to yield the corresponding compound of Formula 9.

Scheme 6

As shown in Scheme 7, a compound of Formula 11 can be prepared by deprotection of a compound of Formula 13 wherein Y ⁵ is a protecting group. For example, when Y ⁵ is methyl, a compound of Formula 11 can be prepared by treatment with boron tribromide in a solvent such as dichloromethane, acetonitrile or 1,4-dioxane, or without a solvent at temperatures ranging from 0 °C to 150 °C. Alternatively, a compound of Formula 11 can be prepared by deprotection of a compound of Formula 13 wherein Y ⁵ is a benzyl group by catalytic hydrogenation in a hydrogen gas atmosphere at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.

Scheme 7

A compound of Formula 13a (wherein W ¹ is O or S, and W ² is O, and X ² is a halogen) can be prepared by reduction followed by a Sandmeyer reaction from a compound of Formula 14. Reduction of the nitro group on a compound of Formula 14 can be achieved by treatment with iron powder in acetic acid at a temperature ranging from 0 °C to 100 °C as shown in Scheme 8 Alternatively, the reduction can be carried out by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature. Halogenation of the resulting amine is facilitated by diazotization with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) followed by treatment with a copper (I) and/or copper (II) halide in a solvent such as acetonitrile at a temperature ranging from 0 °C to the reflux temperature of the solvent to give the corresponding compound of Formula 13a wherein X ² is a halogen such as chloride or bromide.

Scheme 8

14 13a

W ¹ is O or S W ¹ is O or S, W ² is O W ² is O and X is halogen

As shown in Scheme 9, a compound of Formula 14a (wherein W ¹ is O or S) can be prepared by the reaction of a compound of Formula 15 with a compound of Formula 16 (wherein W ¹ is O or S, and W ² is O) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide at temperatures ranging from 0 °C to 150 °C. General methods useful for preparing a compound of Formula 15 are known. See, for example, WO 02/098227 or US 7,548,072 B2.

Scheme 9

15 14a As shown in Scheme 10, a compound of Formula 12 can be prepared by reaction of a compound of Formula 17 (wherein W ¹ is O or S) with a compound of Formula 18 wherein Y ⁶ is a leaving group such as fluoride, chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide. A compound of Formula 18 is commercially available or its preparation is known.

Scheme 10

, 17 Q ¹ is CH or N

W ¹ is O or S

As shown in Scheme 11, a compound of Formula Id (wherein W ¹ is O or S) can be prepared by the reaction of a compound of Formula 17 (wherein W ¹ is O or S) with a compound of Formula 20 wherein the A ring is substituted with an appropriate leaving group Y ⁷. Note the A ring in this Scheme is from Exhibit 1 wherein the bond projecting to the left is connected to Y ⁷ and the bond projecting to the right is connected to W ² in Formula 20. For example, a compound of Formula 20 wherein the A ring is lacking sufficiently electron- withdrawing substituents (i.e. R ²), the use of a metal catalyst (e.g., metal or metal salt) in amounts ranging from catalytic up to superstoichiometric can facilitate the reaction. Typically the leaving group Y ⁷ on a compound of Formula 20 is Br, I or a sulfonate such as OS(0) ₂CF ₃ or OS(0)2(CF ₂)3CF ₃. For example, copper salt complexes (e.g., Cul with NN- dimethylethylenediamine, proline, picolinic acid or bipyridyl), palladium complexes (e.g., tris(dibenzylideneacetone)dipalladium(0) (i.e. Pd ₂(dba) ₃)) or palladium salts (e.g., palladium acetate) with ligands such as 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (i.e. "Xantphos"), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (i.e. "Xphos"), (i?)-l- [(5'p)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-buty lphosphine (i.e. CyPFtBu, "Joshphos") or 2,2'-bis(diphenylphosphino)-l, -binaphthalene (i.e. "BINAP"), in the presence of a base such as potassium carbonate, potassium phosphate (K ₃P0 ₄), cesium carbonate, sodium phenoxide or sodium tert-butoxide, in a solvent such as N,N-dimethylformamide, 1 ,2-dimethoxy ethane, dimethyl sulfoxide, 1,4-dioxane or toluene, optionally mixed with alcohols such as ethanol, can be used. A compound of Formula 20 is commercially available or its preparation is known. General methods useful for preparing a compound of Formula 17 are known. See, for example, WO 02/098227, US 7,548,072 or

EP 1,255,047 wherein W ¹ is O, and EP 1,122,244 wherein W ¹ is S.

Scheme 11

Synthesis of a compound of Formula 21 can be prepared as shown in Scheme 12. A compound of Formula 21 wherein Y ⁸ is a sulfonate leaving group such as trifluoroethanesulfonyl or nonafluorobutylsulfonyl can be prepared by reaction of a phenol of Formula 17a with sulfonating agents such as trifluoromethanesulfonyl chloride trifluoromethanesulfonyl chloride or nonafluorobutylsulfonyl chloride in the presence of base such as triethylamine or pyridine.

Scheme 12

17a 21

As shown in Scheme 13 a compound of Formula 1 can be prepared by a two-step procedure by first reacting a compound of Formula 22 (wherein W ¹ is O or S) with a compound of Formula 21 containing a sulfonate leaving group Y ⁸ to give a compound of Formula 25 by the cross coupling methods previously described for Scheme 11. Note the A ring in this Scheme is from Exhibit 1 wherein the bond projecting to the left is connected to W ¹ and the bond projecting to the right is connected to Y ⁹ in Formula 22. Subsequent reaction of a compound of Formula 25 wherein Y ⁹ is a leaving group such as fluoride, chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) with a compound of Formula 10 as previously described for Scheme 5 or by the cross coupling methods using a compound of Formula 10, as previously described for Scheme 11 (including wherein W ² is NR ⁹). A compound of Formula 22 is commercially available or its preparation is known. Scheme 13

Alternatively, as shown in Scheme 14 a compound of Formula 1 can be prepared by reaction of a compound of Formula 23 wherein W ¹ is O or S with a compound of Formula 21 containing a sulfonate leaving group Y ⁸ using the cross coupling methods as previously described for Scheme 11. A compound of Formula 23 is commercially available or its preparation is known.

Scheme 14

W ¹ is O or S

A compound of Formula 1 can also be prepared by the two-step procedure shown in Scheme 15. A compound of Formula 26 can be prepared by reaction of a compound of Formula 21 containing a sulfonate leaving group Y ⁸ with a compound of Formula 24 wherein W ¹ is O or S by the cross-coupling methods previously described for Scheme 11. Subsequent reaction of a compound of Formula 26 wherein Y ¹⁰ is a protecting group such as a methyl or benzyl group can be deprotected using methods described previously for Scheme 7. A compound of Formula 26 wherein Y ¹⁰ is a protecting group such as an acetyl protecting group (wherein W ² is NR ⁹) can be deprotected by boron trifluoride-methanol complex in solvents such as methanol or dichloromethane at a temperature ranging from 0 °C to 100 °C. Reaction of a comound of Fomula 7 according to the conditions as described for Scheme 3 for a compound of Formula 5 or according to the conditions described for Scheme 4 for a comound of Forumla 5a can be employed to prepare a compound of Formulae lb or lc wherein W ² is NR ⁹ A compound of Formula 24 is commercially available or its preparation is known. Scheme 15

As shown in Scheme 16, a compound of Formula 1 can also be prepared by reacting a compound of Formula 30 wherein L ¹ is amino or a protected amino (e.g., such as an amide, carbamate or nitro) group by methods known in the art. See, for example, WO 2007/083090, WO 2002/098227 or US 7,548,072.

several steps

protected amino

A compound of Formula 30 can be prepared from a compound of Formula 28 (wherein Y ⁹ is the same as Y ⁹ in a compound of Formula 25 above) as shown in Scheme 17. A compound of Formula 28 (wherein Y ⁹ is the same as Y ⁹ in a compound of Formula 25) can be prepared from a compound of Formula 27 (wherein Y ⁸ is the same as Y ⁸ in a compound of Formula 21) and a compound of Formula 22 as previously described in Scheme 13. Note the A ring in this Scheme is from Exhibit 1 wherein the bond projecting to the left is connected to W ¹ and the bond projecting to the right is connected to Y ⁹ in Formula 28. A compound of Formula 27 is commercially available or its preparation is known in the art.

Scheme 17

protected amino A compound of Formula 30 can also be prepared from a compound of Formula 29 (wherein Y ¹⁰ is the same as Y ¹⁰ in a compound of Formula 26) as shown in Scheme 18. A compound of Formula 29 can be prepared by reaction of a compound of Formula 24 with a compound of Formula 27 (wherein Y ⁸ is same as Y ⁸ in a compound of Formula 21) using methods described previously for Scheme 15.

Scheme 18

Alternatively, a compound of Formula 30 can be prepared directly from a compound of Formula 27 (wherein Y ⁸ is same as Y ⁸ in a compound of Formula 21) by reaction with a compound of Formula 23 as shown in Scheme 19 by the cross-coupling reactions as described previously for Schemes 11 and 14.

Scheme 19

27 *~ 30

A compound of Formula lg can be prepared by the procedure shown in Scheme 20. A compound of Formula le wherein R ^ is an allyoxy or benzyloxy group can be prepared by a trans-esterification reaction from a compound of Formula Id. For example when R ^a is a lower alkoxy group such as methoxy and ethoxy it can be reacted with allyl alcohol or benzyl alcohol respectively in the presence of indium chloride or sodium carbonate at a temperature ranging from 0 °C to 120 °C. A compound of Formula le can also be prepared by the method previously described for Schemes 3 or 4 (including wherein R ⁴ is allyloxy or benzyloxy). Subsequent reaction of a compound of Formula le wherein R ^ is allyloxy can be hydrolyzed using tetrakis(triphenylphospine)palladium(0) in the presence of /?-toluenesulfmic acid sodium salt, morpholine or tributyltin hydride in inert solvents such as dichloromethane, tetrahydrofuran or methanol. Reaction of a compound of Formula le wherein R ^ is benzyloxy can be hydrolyzed by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol or ethyl acetate at ambient temperature to prepare a compound of Formula If. A compound of Formula lg wherein R ^c is an alkoxy group or alkylamino group can be prepared from an acid of Formula If with the corresponding alcohol or amine by an esterification reaction in the presence of 0-(7- azabenzotriazol-l-y^-A .A .N' _^N'-tetramethyluronium hexafluorophosphate (i.e. HATU) or 2-chloro-l-methylpyridinium iodide and a base such as triethylamine or N,N-diisopropylethylamine at a temperature ranging from 0 °C to 100 °C. Alternatively, a compound of lg can be prepared from a compound of If using Mitsunobu conditions using triphenylphosphine in the presence of diisopropyl azodicarboxylate or diethyl azodicarboxylate. A compound of Formula lg wherein R ^c is an alkoxy group can also be prepared from an acid of Formula If with an alkylating agent such as di-tert-butyl dicarbonate or R ^4c'OCH ₂Cl (wherein R ^c' is for example a lower alkyl, lower alkylsilyl or phenyl) in the presence of base such as triethylamine, 4-dimethylaminopyridine or N,N-diisopropylethylamine.

Scheme 20

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H ⁺ (molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP ⁺). ¾ NMR spectra are reported at 400 MHz in ppm downfield from tetramethylsilane in CDCI ₃ unless otherwise noted; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet and "br s" means broad singlet.

EXAMPLE 1

Preparation of ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-

1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetate (Compound 2) Step A: Preparation of ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phen oxy]-2- ethoxyacetate

To a solution of 3-[4-chloro-2-fluoro-5-(2-hydroxyphenoxy)phenyl]-l-methyl-6- (trifluoromethyl)-2,4(lH,3H)-pyrimidinedione (450 mg, 1.05 mmol) (prepared as described in WO 02/098227) in N,N-dimethylformamide (5 mL) was added potassium carbonate (289 mg, 2.1 mmol) under a nitrogen atmosphere at ambient temperature. 2-Chloro-2-ethoxy acetic acid ethyl ester (350 mg, 2.10 mmol) was added at the same temperature. The reaction mixture was heated to 50 °C for 16 h, and then allowed to cool. The resulting reaction mixture was filtered and the potassium carbonate was rinsed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (380 mg).

!H NMR δ 7.40 (d, 1H), 7.20 (m, 1H), 7.10 (m, 1H), 7.00 (m, 2H), 6.75 (d, 1H), 6.25 (s, 1H), 5.50 (s, 1H), 4.20 (q, 2H), 3.80 (m, 1H), 3.70 (m, 1H), 3.50 (s, 3H), 1.25 (m, 6H).

EXAMPLE 2

Preparation of methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-

1 (2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-ethoxyacetate (Compound 4) Step A: Preparation of methyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phen oxy]-2- ethoxyacetate

To a solution of compound ethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-ethoxyacetate (i.e. the product of Example 1) (238 mg, 0.43 mmol) in methyl alcohol (5 mL) was added sodium carbonate (476 mg, 4.5 mmol) under a nitrogen atmosphere at ambient temperature. The reaction mixture was heated to 70 °C for 2 h, and then allowed to cool. The resulting reaction mixture was filtered and the sodium carbonate was washed with ethyl acetate. The combined filtrates were concentrated in vacuo. The residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (177 mg).

in NMR δ 7.40 (d, 1H), 7.20 (d, 1H), 7.10-7.00 (m, 3H), 6.73 (m, 1H), 6.25 (s, 1H), 5.53 (d, 1H), 3.80-3.60 (m, 2H), 3.75 (s, 3H), 3.50 (s, 3H), 1.23 (t, 3H).

EXAMPLE 3

Preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)- 1 (2H)-pyrimidinyl] -4-fluorophenoxy] -2-pyridinyl]oxy] -2-methoxyacetate

(Compound 8)

Step A: Preparation of 3-[2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]-4-nitrophenyl]-l- methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione

A mixture of 3-(2,5-difiuoro-4-nitrophenyl)-l-methyl-6-(trifluoromethyl)- 2,4(lH,3H)- pyrimidinedione (2.25 g, 6.4 mmol) (prepared as described in WO 02/098227), 2-methoxy- 3-pyridinol (800 mg, 6.4 mmol) and potassium carbonate (1.06 g, 7.68 mmol) in N,N- dimethylformamide (15 mL) was heated to 70 °C for 2 h, then allowed to cool. The resulting reaction mixture was filtered and the potassium carbonate was washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the resulting residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as a light brown solid (2.82 g).

in NMR δ 7.90 (d, 1H), 7.40 (m, 1H), 6.93 (m, 2H), 6.76 (m, 1H), 6.32 (s, 1H), 3.92 (s, 3H), 3.53 (s, 3H). Ste B: Preparation of Compound 3-[4-amino-2-fluoro-5-[(2-methoxy-3- pyridinyl)oxy]phenyl]- 1 -methyl-6-(trifluoromethyl)-2,4(lH,3H)- pyrimidinedione

To a mixture of iron powder (3.5 g, 62.7 mmol), acetic acid (20 mL) and water (2 mL) was added dropwise a solution of 3-[2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]-4- nitrophenyl]-l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimid inedione (i.e. the product of Step A) (2.82 g, 6.18 mmol) in acetic acid (10 mL), while the temperature of the reaction mixture was kept at 35 °C or lower. After completion, the reaction mixture was stirred for 2 h and then filtered through Celite® diatomaceous filter aid. The filtrate was diluted with ethyl acetate. The mixture was neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give the title compound as a light yellow foam (2.61 g).

in NMR δ 7.90 (m, 1H), 7.18 (m, 1H), 6.84 (m, 1H), 6.60 (m, 2H), 6.31 (2, 1H), 4.15 (br s, 2H), 4.00 (s, 3H), 3.51 (s, 3H).

Step C: Preparation of 3-[4-chloro-2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]phenyl]- l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione

Isoamyl nitrite (3.13 g, 26.7 mmol) was added dropwise to a mixture of 3-[4-amino-2- fluoro-5-[(2-methoxy-3-pyridinyl)oxy]phenyl]-l-methyl-6-(tri fluoromethyl)-2,4(lH,3H)- pyrimidinedione (i.e. the product of Step B) (2.61 g, 6.13 mmol), copper (I) chloride, (1.17 g, 5.88 mmol) and copper (II) chloride (2.5 g, 10.7 mmol) in acetonitrile (50 mL) at room temperature and the reaction mixture was stirred for 1 h at the same temperature. The reaction mixture was poured into 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatograpy eluting with ethyl acetate in hexanes to give the title compound as a light brown solid (1.60 g).

!H NMR δ 7.95 (d, 1H), 7.40 (d, 1H), 7.20 (d, 1H), 6.85 (m, 1H), 6.67 (d, 1H), 6.32 (s, 1H), 3.98 (s, 3H), 3.52 (s, 3H).

Step D: Preparation of 3-[4-chloro-5-[(l ,2-dihydro-2-oxo-3-pyridinyl)oxy]-2- fluorophenyl]-l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimi dinedione A mixture of 3-[4-chloro-2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]phenyl]-l -methyl-6- (trifluoromethyl)-2,4(lH,3H)-pyrimidinedione (i.e. the product of Step C) (1.45 g, 3.3 mmol) and boron tribromide (1.9 mL, 19.6 mmol) in dichloromethane (20 mL) was stirred at room temperature for 2 days. The reaction mixture was slowly quenched with 1 N hydrochloric acid, and the reaction mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as a light brown solid (1.12 g).

!H NMR δ 13.4 (br s, 1H), 7.40 (d, 1H), 7.26 (m, 1H), 7.00-6.95 (m, 2H), 6.32 (s, 1H), 6.20 (m, 1H), 3.52 (s, 3H).

Step E: Preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]-2-p yridinyl]oxy]-2- methoxyacetate

To a solution of compound 3-[4-chloro-5-[(l,2-dihydro-2-oxo-3-pyridinyl)oxy]-2- fluorophenyl]-l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimi dinedione (i.e. the product of Step D) (100 mg, 0.23 mmol) in acetonitrile (1.5 mL) and N,N-dimethylformamide (0.5 mL) was added potassium carbonate (64 mg, 0.46 mmol) under a nitrogen atmosphere at ambient temperature. 2-Bromo-2-methoxy acetic acid methyl ester (42 mg, 0.24 mmol) was added at the same temperature. The reaction mixture was heated to 60 °C for 2 h, and then allowed to cool. The resulting reaction mixture was filtered and the solid potassium carbonate was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the 3 - [2-chloro-5 - [3 ,6-dihydro-3 -methyl-2,6-dioxo-4-(trifluoromethyl)- 1 (2H)-pyrimidinyl] - 4-fluorophenoxy]-2-hydroxy-a-methoxy-l(2H)-pyridineacetic acid (20 mg) as white foam and the title compound as a white foam (55 mg).

in NMR: δ 7.91 (d, 1H), 7.40 (d, 1H), 7.30 (m, 1H), 6.93 (m, 1H), 6.82 (d, 1H), 6.30 (s, 1H), 6.18 (d, 1H), 3.78 (s, 3H), 3.52 (s, 3H), 3.48 (s, 3H).

!H NMR of 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluorome thyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]-2-hydroxy-a-methoxy-l(2H)-pyri dineacetic acid: δ 7.40 (d, 1Η), 7.21 (d, 1Η), 7.00 (d, 1Η), 6.81 (d, 1Η), 6.50 (s, 1Η), 6.30 (s, 1Η), 6.20 (t, 1Η), 3.81 (s, 3Η), 3.55 (s, 3Η), 3.48 (s, 3Η).

EXAMPLE 4

Preparation of ethyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluo romethyl)-

1 (2H)-pyrimidinyl]-4-fluorophenoxy]-2-pyridinyl]oxy]-2-methox yacetate (Compound 9) Step A: Preparation of ethyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]-2-p yridinyl]oxy]-2- methoxyacetate

To a solution of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]-2-pyri dinyl]oxy]-2-methoxyacetate (i.e. the product of Example 3) (163 mg, 0.31 mmol) in ethyl alcohol (5 mL) was added sodium carbonate (40 mg, 0.38 mmol) under a nitrogen atmosphere at ambient temperature. The reaction mixture was heated to 65 °C for 2 h, and then allowed to cool. The resulting reaction mixture was filtered and the precipitate was washed with ethyl acetate. The combined filtrates were concentrated in vacuo. The residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (130 mg).

!H NMR δ 7.90 (d, 1H), 7.39 (d, 1H), 7.25 (m, 1H), 6.92 (m, 1H), 6.82 (d, 1H), 6.25 (s, 1H), 6.10 (d, 1H), 4.25 (q, 2H), 3.50 (s, 3H), 3.47 (s, 3H), 1.25 (t, 3H).

EXAMPLE 5

Alternate preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)- 1 (2H)-pyrimidinyl] -4-fluorophenoxy] -2-pyridinyl]oxy] -2-methoxyacetate

(Compound 8)

Step A: Preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]-2-p yridinyl]oxy]-2- methoxyacetate

To a solution of 3-[4-chloro-2-fluoro-5-(2-hydroxyphenoxy)phenyl]-l-methyl-6- (trifluoromethyl)-2,4(lH,3H)-pyrimidinedione (i.e. the product of Example 4, Step D) (450 mg, 1.05 mmol) (5.28 g, 12.3 mmol) and potassium carbonate (4.75 g, 34.4 mmol) in acetonitrile (45 mL) under a nitrogen atmosphere at ambient temperature was added a solution of 2-chloro-2-methoxy acetic acid methyl ester (2.39 g, 16.1 mmol) in acetonitrile (3 mL) dropwise. The reaction mixture was stirred for 6.5 h at room temperature and concentrated under reduced pressure. The resulting reaction mixture was filtered and the potassium carbonate was rinsed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (5.58 g).

in NMR (300 MHz) δ 7.38 (d, 1H), 7.22 (m, 1H), 7.15-6.99 (m, 3H), 6.74 (m, 1H), 6.29 (s, 1H), 5.48 (d, 1H), 3.76 (s, 3H), 3.50 (s, 3H), 3.47 (s, 3H). ESI-MS m/z 533 [M+H].

EXAMPLE 6

Preparation of 2-propen-l-yl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacetate

(Compound 123)

Step A: Preparation of 2-propen-l-yl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6- dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy ]phenoxy]-2- methoxyacetate

To a stirred solution of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]-2-pyri dinyl]oxy]-2-methoxyacetate (i.e. the product of Example 5) (6.25 g 1 1.7 mmol) in allyl alcohol (66 mL) was added InCl3 (3.17 g, 14.3 mmol) and heated at 75-82 °C for 9 h. The resulting reaction mixture was filtered and the collected solid was rinsed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (6.32 g).

!H NMR δ 7.37 (d, 1H), 7.23 (m, 1H), 7.14-6.99 (m, 3H), 6.74 (m, 1H), 6.29 (d, 1H), 5.93- 5.82 (m, 1H), 5.50 (d, 1H), 5.32-5.28 (m, 1H), 5.23 (d, 1H), 4.66 (d, 2H), 3.50 (s, 3H), 3.48 (s, 3H). ESI-MS m/z 581 [M+Na].

EXAMPLE 7

Preparation of 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetic acid (Compound 126) Step A: 2 2 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4 trifiuoromethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetic acid To a solution of 2-propen-l-yl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacetate (i.e. the product of Example 6) (5.42 g, 9.70 mmol) in 55 mL of a 3: 1 tetrahydrofuran/methanol solution at ambient temperature was added /?-toluenesulfinic acid sodium salt (2.37 g, 12.7 mmol) in 10 mL of a 1 : 1 tetrahydrofuran/methanol solution followed by tetrakis(triphenylphospine)palladium(0) (459 mg, 0.40 mmol). The reaction mixture was stirred for 6 h and concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate (90 mL), dichloromethane (30 mL) and water (15 mL), and the layers were separated. The organic layer was washed with saturated ammonium chloride solution (2x40 mL) and brine (2x40 mL), dried over anhydrous Na ₂S0 ₄, filtered and concentrated under reduced pressure. The crude syrupy residue was diluted with dichloromethane (15 mL) and triturated with hexanes (35 mL). A free-flowing precipitate was decanted, leaving a residual syrup. The process of diluting with dichloromethane, triturating with hexanes and decanting the free flowing precipitate was repeated until all the residual syrup appeared as free flowing precipitate in dichloromethane/hexanes solution. The precipitate was filtered onto Buchner funnel, rinsed with hexanes (75 mL) and 60% tert-butyl methyl ether in hexanes (130 mL), then dried under vacuum to provide the title compound as light yellow powdery solid (4.05 g, semi-pure). About 700 mg of semi-pure product was further purified by reverse-phase CI 8 Combi- flash column chromatography (30 g cartridge size, over 6 loadings, 3X for -120-150 mg and 3X for -170-280 mg loadings) eluting with a gradient of 5% to 100% methanol in water to afford of the title compound as white amorphous solid (420 mg). MP = 163-166 °C.

in NMR (CD ₃OD) δ 7.50 (d, 1H), 7.23 (d, 1H), 7.09 (m, 1H), 7.01-6.94 (m, 3H), 6.34 (s, 1H), 5.20 (s, 1H), 3.46 (s, 3H), 3.35 (d, 3H). ESI-MS m/z 517 [M-H]. EXAMPLE 8

Preparation of cyclobutyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacet

(Compound 144)

Step A: cyclobutyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phen oxy]-2- methoxyacetate

To a solution of 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacetic acid (i.e. the product of Example 7) (68.8 mg, 0.133 mmol), cyclobutanol (32 μΕ, 29.4 mg, 0.408 mmol) and N,N-diisopropylethylamine (0.104 mL, 0.597 mmol) in tetrahydrofuran (3 mL) was added 2-chloro-l-methylpyridinium iodide (108 mg, 0.410 mmol) in 1 portion and the resulting mixture stirred at room temperature for 21 h, during which time a solid formed. The mixture was filtered, rinsed with tetrahydrofuran (5 mL) and the filtrate concentrated under reduced pressure to give a yellowish residue which was purified by preparative thin- layer chromatography eluting with 1 :2 ethyl acetate in hexanes to afford the title compound as a low-melting white solid (50 mg). MP = 44-47 °C.

in NMR δ 7.38 (d, 1H), 7.22 (d, 1H), 7.14-6.99 (m, 3H), 6.74 (m, 1H), 6.29 (d, 1H), 5.44 (d, 1H), 5.04 (m, 1H), 3.50 (s, 3H), 3.46 (s, 3H), 2.37-2.29 (m, 2H), 2.15-2.00 (m, 2H), 1.79 (m, 2H). ESI-MS m/z 595 [M+Na].

EXAMPLE 9

Preparation of 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluor omethyl)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-N,2-dimethoxyacetamide (Compound 142) Step A: 2 2 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifiuoromethy l)-l(2H)- pyrimidinyl]-4-fluorophenoxy]phenoxy]-N,2-dimethoxyacetamide

To a solution of 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacetic acid (i.e. the product obtained in Example 7) (119 mg, 0.229 mmol), O-(7-azabenzotriazol-l-yl)- hexafluorophosphate (97 mg, 0.26 mmol) and N,N-diisopropylethylamine (175 μί, 1.01 mmol) in tetrahydrofuran (5.5 mL) was added methoxylamine hydrochloride (69.7 mg, 0.818 mmol) in one portion and the resulting mixture was stirred at ambient temperature for 19 h. The reaction mixture was concentrated under reduced pressure and purified by preparative thin-layer chromatography eluting with 1 : 1 ethyl acetate in hexanes to afford the title compound as a white solid (75 mg). MP = 66- 69 °C.

lH NMR δ 9.25 (d, 1Η), 7.41 (d, 1Η), 7.24-7.10 (m, 4Η), 6.66 (d, 1Η), 6.32 (d, 1Η), 5.42 (d, 1Η), 3.69 (d, 3Η), 3.52 (s, 3Η), 3.43 (d, 3Η). ESI-MS m/z 548 [Μ+Η]. EXAMPLE 10

Preparation of 2-methoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacet

(Compound 143)

Step A: 2-methoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-

(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phen oxy]-2- methoxyacetate

To a solution of 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy ]-2-methoxyacetic acid (i.e. the product obtained in Example 7, 69 mg, 0.133 mmol) and N,N-diisopropylethylamine (150 μί, 0.861 mmol) in tetrahydrofuran (4 mL) was added chloromethyl methyl ether (55 μί, 0.56 mmol) dropwise and the resulting mixture stirred at ambient temperature for 18 h. The reaction mixture was concentrated under reduced pressure and purified by preparative thin-layer chromatography eluting with 1 :2 ethyl acetate in hexanes) to afford the title compound as a light yellow gum (44 mg).

!H NMR δ 7.38 (d, 1H), 7.24 (d, 1H), 7.14-7.00 (m, 3H), 6.75 (m, 1H), 6.28 (s, 1H), 5.50 (d, 1H), 5.30 (q, 2 H), 3.50 (s, 6H), 3.38 (s, 3H). ESI-MS m/z 585 [M+Na].

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 through 13 can be prepared. The following abbreviations are used in the Tables which follow: n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, z ^'-Pr means isopropyl, Bu means butyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, -CN means cyano, and Ph means phenyl.

ft ⁵ is OCH ₃

OH O-n-Bu OPh

OCH3 O-z ^'-Bu OCH ₂Ph OCH ₂CH ₃ OCH ₂CH=CH ₂ O-c-pentyl OCH ₂CH ₂CH ₃ O-w-pentyl O-c-hexyl OCH(CH ₃) ₂ OCH ₂C≡CH OCH ₂C(=0)OCH ₃ R4 R^

OCH ₂CH2CH ₂Si(CH3)3 O H ₃N ⁺hexyl CP N+(Me) ₄

NHPh O H ₃N ⁺octyl Cr N ⁺(Me) ₃CH ₂Ph O H ₄N+ O H ₃N ⁺hexadecyl Cr S ⁺(Me) ₃ O H ₃N+Me O ^" H ₃N ⁺octadecyl 0 ^~ K+

O H ₃N ⁺z-Pr O H ₃N ⁺cyclohexyl 0 ^~ Na ⁺

O H ₃N ⁺«-Prr O- H ₂N+(Et) ₂ cr Li

O H ₃N ⁺«-butyl O HN ⁺(Et) ₃

The present disclosure also includes Tables 1A through 1Q, each of which is constructed the same as Table 1 above except that the Table Header Row in Table 1 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row shown below. For example, in Table 1 A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 1 above. Thus, the first entry in Table 1A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables IB through 1Q are constructed similarly.

Table Table Header Row Table Table Header Row Table Table Header Row

1A R ⁵ is OEt 1G R ⁵ is S-z-Pr 1M R ⁵ is F

IB R ⁵ is O-n-Pr 1H R ⁵ is NHMe IN R ⁵ is CI

1C R ⁵ is O-z ^'-Pr 11 R ⁵ is NHEt lO R ⁵ is Br

ID R ⁵ is SMe 1J R ⁵ is NMe IP R ⁵ is CF ₃

IE R ⁵ is SEt IK R ⁵ is NH-«-Pr iQ R ⁵ is CN

IF R ⁵ is S-n-Pr 1L R ⁵ is OH

TABLE 1.1

Table 1.1 is constructed the same way as Table 1 except the structure below repl the header structure in Table 1.

The present disclosure also includes Tables 1.1 A through 1.1Q, each of which is constructed the same as Table 1.1 above except that the Table Header Row in Table 1.1 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 1.1 A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 1.1 above. Thus, the first entry in Table 1.1 A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables L IB through 1.1Q are constructed similarly. TABLE 1.2

Table 1.2 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 1.2A through 1.2Q, each of which is constructed the same as Table 1.2 above except that the Table Header Row in Table 1.2 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 1.2A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 1.2 above. Thus, the first entry in Table 1.2A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 1.2B through 1.2Q are constructed similarly.

TABLE 2

Table 2 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 2A through 2Q, each of which is constructed the same as Table 2 above except that the Table Header Row in Table 2 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 2A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 2 above. Thus, the first entry in Table 2A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 2B through 2Q are constructed similarly.

TABLE 3

Table 3 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 3A through 3Q, each of which is constructed the same as Table 3 above except that the Table Header Row in Table 3 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 3 A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 3 above. Thus, the first entry in Table 2A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 3B through 3Q are constructed similarly.

TABLE 4

Table 4 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.

The present disclosure also includes Tables 4A through 4Q, each of which is constructed the same as Table 4 above except that the Table Row Header in Table 4 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 4A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 4 above. Thus, the first entry in Table 4A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 4B through 4Q are constructed similarly.

TABLE 5

Table 5 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 5A through 5Q, each of which is constructed the same as Table 5 above except that the Table Header Row in Table 5 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 5 A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 5 above. Thus, the first entry in Table 5A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 5B through 5Q are constructed similarly.

TABLE 6

Table 6 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.

The present disclosure also includes Tables 6A through 6Q, each of which is constructed the same as Table 6 above except that the Table Header Row in Table 6 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 6A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 6 above. Thus, the first entry in Table 6A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 6B through 6Q are constructed similarly.

TABLE 7

Table 7 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 7A through 7Q, each of which is constructed the same as Table 7 above except that the Table Header Row Table 7 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 7A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 7 above. Thus, the first entry in Table 7A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 7B through 7Q are constructed similarly.

TABLE 8

Table 8 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.

The present disclosure also includes Tables 8A through 8Q, each of which is constructed the same as Table 8 above except that the Table Header Row in Table 8 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above. For example, in Table 8A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 8 above. Thus, the first entry in Table 8A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 8B through 8Q are constructed similarly.

TABLE 9

Table 9 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 9A through 9Q, each of which is constructed the same as Table 9 above except that the Table Header Row in Table 9 (i.e. "R ⁵ is OMe") is replaced with the respective r Table Header Row defined in Tables 1 A through 1Q above. For example, in Table 9A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 9 above. Thus, the first entry in Table 9A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 9B through 9Q are constructed similarly.

TABLE 10

Table 10 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 10A through 10Q, each of which is constructed the same as Table 10 above except that the Table Header Row in Table 10 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above. For example, in Table 10A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 10 above. Thus, the first entry in Table 10A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 10B through 10Q are constructed similarly.

TABLE 10.1

Table 10.1 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 10.1 A through 10.1Q, each of which is constructed the same as Table 10.1 above except that the Table Header Row in Table 10.1 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above. For example, in Table 10.1 A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 10.1 above. Thus, the first entry in Table 10.1 A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 10. IB through 10.1Q are constructed similarly.

TABLE 11

Table 11 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.

The present disclosure also includes Tables 11A through HQ, each of which is constructed the same as Table 11 above except that the Table Header Row in Table 11 (i.e. "R ⁵ is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above. For example, in Table 11A the Table Header Row is "R ⁵ is OEt" and R ⁴ is as defined in Table 11 above. Thus, the first entry in Table 11 A specifically discloses a compound of Formula 1 wherein R ⁴ is OH and R ⁵ is OEt. Tables 1 IB through HQ are constructed similarly.

R ⁴ R ⁴ OMe SMe OMe SMe OEt SEt OEt SEt

A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Weight Percent

Active

Ingredient Diluent Surfactant

Water-Dispersible and Water- 0.001-90 0-99.999 0-15

soluble Granules, Tablets and

Powders

Oil Dispersions, Suspensions, 1-50 40-99 0-50

Emulsions, Solutions

(including Emulsifiable

Concentrates)

Dusts 1-25 70-99 0-5

Granules and Pellets 0.001-99 5-99.999 0-15

High Strength Compositions 90-99 0-10 0-2

Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy- 4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C ₆-C ₂2), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as "surface-active agents") generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides. Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μιη can be wet milled using media mills to obtain particles with average diameters below 3 μιη. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μιη range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry 's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al, Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

Example A

High Strength Concentrate

Compound 5 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%

Example B

Wettable Powder

Compound 55 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0%> sodium silicoaluminate 6.0%> montmorillonite (calcined) 23.0%

Example C

Granule

Compound 24 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet

Compound 126 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0%> sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate

Compound 24 10.0% polyoxyethylene sorbitol hexoleate 20.0% C ₆-C ₁₀ fatty acid methyl ester 70.0%>

Example F

Microemulsion

Compound 5 5.0%> polyvinylpyrrolidone -vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0%> glyceryl monooleate 15.0% water 20.0%

Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent as herbicides and/or plant growth regulants. These compounds generally show highest activity for postemergence weed control and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of the invention are particularly useful for selective control of weeds in perennial plantation crops such as sugarcane and citrus. Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both postemergent and preemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation. A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.00025 to 20 kg/ha with a preferred range of about 0.002 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a herbicidally effective amount of a compound of Formula 1 and a biologicially effective amount of at least one additional biologically active compound or agent and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminopyralid, aminocyclopyrachlor and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop- propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, CUH-35 (2-methoxyethyl 2-[[[4-chloro-2-fluoro-5-[(l-methyl-2-propynyl)oxy]phenyl](3 - fluorobenzoyl)amino]carbonyl]- 1 -cyclohexene- 1 -carboxylate), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, HOK-201 (N-(2,4- difluorophenyl)- 1 ,5 -dihydro-N-( 1 -methylethyl)-5 -oxo- 1 - [(tetrahydro-2H-pyran-2-yl)- methyl]-4H-l ,2,4-triazole-4-carboxamide), imazamethabenz -methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuran, methabenzthiazuran, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, 4-amino- 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecar boxylic acid (CAS number 943832-60-8), 4-amino-3-chloro-6-(4-chloro-2-fiuoro-3-methoxyphenyl)-2- pyridinecarboxylic acid methyl ester (CAS number 943831-98-9), pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A ₄ and A ₇, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1 :3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.

Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, l-bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, diamuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2 -methyl- 1, 3 -dioxolane (MG 191), dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, H-31868, isoxadifen-ethyl, LAB 147886, M-32988, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride and oxabetrinil to increase safety to certain crops. Antido tally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.

Preferred for better control of undesired vegetation (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of ametryn, aminocyclopyrachlor, aminopyralid, atrazine, bromacil, chlorsulfuron, clomazone, diuron, glufosinate, glufosinate ammonium, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate -potassium, glyphosate -trimesium), hexazinone, imazapic, imazapyr, metsulfuron-methyl, norflurazon oryzalin, paraquat dichloride, pendimethalin, rimsulfuron, simazine, sulfometuron-methyl, triclopyr, triclopyr-butotyl, and triclopyr-triethylammonium.

Specific mixtures (compound numbers refer to compounds in Index Table A are listed in Tables Al through A12. In Table Al, each line below the column headings "Component (a)" and "Component (b)" specifically discloses a mixture of Component (a), which is Compound 1, with a Component (b) herbicide. For example, the first line of Table Al discloses a mixture of Compound 1 with ametryn.

TABLE Al

Component (a) Component (b)

Compound 1 ametryn

Compound 1 aminocyclopyrachlor

Compound 1 aminopyralid

Compound 1 atrazine

Compound 1 bromacil

Compound 1 chlorsulfuron

Compound 1 clomazone

Compound 1 diuron

Compound 1 glufosinate

Compound 1 glyphosate

Compound 1 hexazinone

Compound 1 imazapic

Compound 1 imazapyr

Compound 1 metsulfuron-methyl

Compound 1 norflurazon

Compound 1 oryzalin

Compound 1 Paraquat dichloride

Compound 1 pendimethalin

Compound 1 rimsulfuron Compound 1 simazme

Compound 1 sulfometuron-methyl

Compound 1 triclopyr

Tables A2 through A12 are each constructed the same as Table Al above except that entries below the "Component (a)" column heading are replaced with the respective Component (a) Column Entry shown below. Thus, for example, in Table A2 the entries below the "Component (a)" column heading all recite "Compound 2", and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with ametryn. Tables A3 through A12 are constructed similarly.

Table Number Component (a) Column Entries Table Number Component (a) Column Entries

Compound 2 A8 Compound 8

Compound 3 A9 Compound 9

Compound 4 A10 Compound 10

Compound 5 Al l Compound 11

Compound 6 A12 Compound 12

Compound 7

Table Bl lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. The second column of Table Bl lists the specific Component (b) compound (e.g., "ametryn" in the first entry). The third, fourth and fifth columns of Table Bl lists ranges of weight ratios for rates at which the Component (b) compound is typically applied to a field-grown crop relative to Component (a). Thus, for example, the first line of Table Bl below the column headings specifically discloses the combination of Compound 5 with ametryn is typically applied in a weight ratio between 1 :364 to 3: 1, more typically applied in a weight ratio between 1 : 121 to 1 :2 and most typically applied in a weight ratio between 1 :22 to 1 :4. The remaining lines of Table Bl are constructed similarly.

Table Bl

Typical More Typical Most Typical

Component (a) Component (b)

Weight Ratio Weight Ratio Weight Ratio

Compound 5 ametryn 1:364 to 3:1 1: 121 to 1:2 1:22 to 1:4

Compound 5 aminocyclopyrachlor 1:205 to 6:1 1:68 to 2: 1 9: 1 to 1:2

Compound 5 aminopyralid 1:41 to 112: 1 1: 13 to 38:1 1: 1 to 7: 1

Compound 5 atrazine 1:205 to 6:1 1:68 to 2: 1 l: 17 to 1:3

Compound 5 bromacil 1:768 to 6:1 1:256 to 2: 1 1:24 to 1:3

Compound 5 chlorsulfuron 1: 13 to 336: 1 1:4 to 112:1 2: 1 to 21:1

Compound 5 clomazone 1:74 to 16: 1 1:24 to 6: 1 1:6 to 2: 1 Typical More Typical Most Typical

Component (a) Component (b)

Weight Ratio Weight Ratio Weight Ratio

Compound 5 diuron 1:768 to 6:1 1:256 to 2:1 1:24 to 1:3

Compound 5 glufosinate 1:137 to 9:1 1:45 to 3:1 1:11 to 1:2

Compound 5 glyphosate 1:137 to 9:1 1:45 to 3:1 1:11 to 1:2

Compound 5 hexazinone 1:1028 to 2:1 1:342 to 1:3 1:85 to 1:11

Compound 5 imazapic 1:41 to 112:1 1:13 to 38:1 1:1 to 7:1

Compound 5 imazapyr 1:171 to 27:1 1:57 to 9:1 1:5 to 2:1

Compound 5 metsulfuron-methyl 1:4 to 1120:1 1:1 to 374:1 7:1 to 70:1

Compound 5 norflurazon 1:1509 to 1:2 1:503 to 1:4 1:125 to 1:16

Compound 5 oryzalin 1:1028 to 5:1 1:342 to 2:1 1:32 to 1:4

Compound 5 Paraquat dichloride 1:298 to 4:1 1:99 to 2:1 1:24 to 1:4

Compound 5 pendimethalin 1:380 to 4:1 1:126 to 2:1 1:31 to 1:4

Compound 5 rimsulfuron 1:12 to 96:1 1:4 to 32:1 1:1 to 8:1

Compound 5 simazine 1:13 to 9:1 1:4 to 3:1 1:4 to 2:1

Compound 5 sulfometuron-methyl 1:6 to 17:1 1:2 to 6:1 1:2 to 4:1

Compound 5 triclopyr 1:45 to 3:1 1:15 to 1:2 1:15 to 1:2

Tables B2 through B17 are each constructed the same as Table Bl above except that entries below the "Component (a)" column heading are replaced with the respective Component (a) Column Entry shown below. Thus, for example, in Table B2 the entries below the "Component (a)" column heading all recite "Compound 13", and the first entry below the column headings in Table B2 specifically discloses a mixture of Compound 13 with ametryne is typically applied in a weight ratio between 1:364 to 3:1, more typically applied in a weight ratio between 1:121 to 1:2 and most typically applied in a weight ratio between 1 :22 to 1 :4. Tables B3 through B17 e constructed similarly.

Table Number Component (a) Column Entries Table Number Component (a) Column Entries

B2 Compound 13 B10 Compound 51

B3 Compound 18 Bll Compound 55

B4 Compound 19 B12 Compound 56

B5 Compound 20 B13 Compound 70

B6 Compound 21 B14 Compound 126 B7 Compound 24 B15 Compound 127 B8 Compound 27 B16 Compound 137 B9 Compound 50 B17 Compound 147

The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A, B, C, D, E and F for compound descriptions. The following abbreviations are used in Index Table A, B, C, D and E which follows: c is cyclo, n is normal, t is tertiary, Me is methyl, Et is ethyl, Pr is propyl, Bu is butyl, hex is hexyl, tetrahydropyran-4-yl is a tetrahydopyran ring attached at the 4- position, tetrahydrofuran-2-yl is a tetrahydrofuran ring attached at the 2-position, OMe is methoxy, OEt is ethoxy, SMe is methylthio, Ph is phenyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. Unless otherwise noted, mass spectra are reported in the following tables as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H ⁺ (molecular weight of 1) to the molecule, observed by mass spectrometry using either atmospheric pressure chemical ionization (AP ⁺) or electro-spray ionization (ESI). The abbreviation "Cmpd. No." stands for Compound Number.

Cmpd No. A R5 R ⁴ 1H N.M.R/M.S.

1 A-l F OEt @

2 (Ex. 1) A-l OEt OEt **

3 A-l OMe OMe @

4 (Ex. 2) A-l OEt OMe **

5 A-l OMe OEt @

6 A-l CH ₂OCH ₃ OMe 547

7 A-l CH ₂OH OMe 533 Cmpd No. A R5 R4 1H .M.R/M.S.

8 (Ex. 3,5) A-4 OMe OMe **

9 (Ex. 4) A-4 OMe OEt **

10 A-4 OEt OEt @

11 A-4 OMe O-n-Pr 562

12 A-4 SMe OMe 550

13 A-l OMe 0- -Pr 583*

14 A-l OMe O-w-Bu 597*

15 A-l OMe OCH ₂Ph 631*

16 A-l OMe OCH ₂CH(Me) ₂ 597*

17 A-l OMe OCH(Me)Et 597*

18 A-l OMe OCH ₂-c-Pr 595*

19 A-l OMe OCH ₂CH ₂OMe 599*

20 A-l OMe OCH ₂CH ₂OEt 613*

21 A-l OMe OCH ₂C0 ₂Me 613*

22 A-l OMe OCH ₂C0 ₂Et 627*

23 A-l OMe O-c-pentyl 609*

24 A-l OMe OCH ₂CH ₂CH ₂F 601*

25 A-l OMe OPh 617*

26 A-l OMe OCH ₂CHF ₂ 605*

27 A-l OMe OCH ₂CH ₂Cl 603*

28 A-l OMe OCH ₂CF ₂CHF ₂ 655*

29 A-l OMe OCH ₂C≡CH 579*

30 A-l OMe 0-(4-F-Ph) 635*

31 A-l OMe ONHC(=0)Me 574[M-H]

32 A-l OMe OCH ₂CHF ₂ 587*

33 A-l OMe 0(pyridin-3-yl) 596

34 A-l OMe OCH ₂-c-Bu 609*

35 A-l OMe OCH(Me)-c-Pr 609*

36 A-l OMe OCH ₂CH ₂Br 647*

37 A-l OMe OCH ₂CH ₂SMe 615*

38 A-l OMe OCH ₂CH ₂CH(Me) ₂ 611*

39 A-l OMe ON(Me) ₂ 562

40 A-l OMe 0(tetrahydropyran-4-yl) 625* Cmpd No. A R5 R4 N.M.R/M.S.

41 A-l OMe OCH ₂CH ₂CH(Me)OMe 627*

42 A-l OMe OCH2CF2CF2CF3 723*

43 A-l OMe OCH ₂CH ₂0- -Pr 627*

44 A-l OMe OCH ₂CH ₂C(Me) ₃ 625*

45 A-l OMe O-4-Me-c-hex 637*

46 A-l OMe OCH ₂CH ₂CH ₂OMe 613*

47 A-l OMe OCH(Me)CF ₃ 637*

48 A-l OMe OCH ₂CF ₂CF ₃ 673*

49 A-l OMe OCH CH ₂Ph 645*

51 A-l OMe OCH(Me)C0 ₂Me 627*

52 A-l OMe OCH ₂CF ₂CH ₃ 619*

53 A-l OMe OCH ₂CH ₂CN 594*

54 A-l OMe OCH(Et) ₂ 611*

55 A-l OMe OCH ₂CF ₃ 601

56 A-l OMe O-c-hex 623*

57 A-l OMe OCH ₂-c-pentyl 623*

58 A-l OMe OCH ₂CH ₂SEt 629*

59 A-l OMe O-w-pentyl 611*

60 A-l OMe OCH ₂CH ₂CH(Me)Et 625*

61 A-l OMe OCH ₂CH ₂I 695*

62 A-l OMe OCH(Me)Ph 645*

63 A-l OMe OCH ₂CH ₂SPh 677*

64 A-l OMe OCH(CH ₂F) ₂ 619*

65 A-l OMe OCH ₂CH(OEt) ₂ 657*

66 A-l OMe OCH ₂CH ₂CH ₂Cl 595

67 A-l OMe OCH ₂CH ₂CF ₂CF ₃ 687*

68 A-l OMe OCH(CF ₃) ₂ 669*

69 A-l OMe OCH ₂COEt 611*

70 A-l OMe OCH ₂CH ₂0(CH ₂) ₂OMe 643*

71 A-l OMe OCH ₂CH ₂OC(=0)Me 627* Cmpd No. A R5 R4 ^ N.M.R/M.S.

72 A-l OMe OCH ₂(CH ₂)2CH ₂Cl 631 *

73 A-l OMe OCH ₂C(=0)Ph 659*

74 A-l OMe OCH(Me)CH ₂Cl 617*

75 A-l OMe OCH ₂CH ₂S0 ₂Me 647*

76 A-l OMe OCH ₂CH ₂CH ₂Si(Me) ₃ 655*

77 A-l OMe OCH ₂(CH ₂) ₂CF ₃ 651 *

78 A-l OMe OCH ₂CH(OMe) ₂ 629*

79 A-l OMe OCH ₂CH ₂C≡CMe 607*

80 A-l OMe OCH ₂CH=CHMe 595*

81 A-l OMe OCH ₂CH ₂Si(Me) ₃ 641 *

82 A-l OMe OCH ₂C≡CSi(Me) ₃ 651 *

83 A-l OMe OCH ₂CH ₂CF ₃ 637*

84 A-l OMe OCH ₂CH=C(Me) ₂ 609*

85 A-l OMe OCH ₂CH ₂C(Me)=CH ₂ 609*

86 A-l OMe OCH ₂CH ₂CH ₂C≡CH 607*

87 A-l OMe OCH ₂CH ₂C≡CH 593*

88 A-l OMe OCH ₂CCl ₃ 671 *

89 A-l OMe OCH ₂CH ₂-c-Pr 609*

90 A-l OMe OCH ₂CH ₂CH=CH ₂ 595*

91 A-l OMe OCH ₂C≡CMe 593*

92 A-l OMe OCH ₂CH=CH ₂Si(Me) ₃ 653*

93 A-l OMe OCH ₂(tetrahydro£ i-an-2-yl) 625*

94 A-l OMe OCH ₂OEt 599*

95 A-l OMe OCH ₂OCH ₂Ph 661 *

96 A-l OMe OCH ₂OCH ₂CH ₂OMe 629*

97 A-l OMe OCH ₂OCH ₂CH ₂Si(Me) ₃ 671 *

98 A-l OMe N(Me) ₂ 546

99 A-l OMe NHPh 594

100 A-l OMe NHEt 568*

101 A-l OMe NHOEt 562

102 A-l OEt O-z-Pr 597*

103 A-l OEt OCH ₂Ph 645*

104 A-l OEt OCH ₂CH(Me) ₂ 611 * Cmpd No. A R5 R4 ^lU N.M.R/M.S.

105 A-l OEt NHEt 560

106 A-3 OMe OEt 547

107 A-3 OMe OMe 533

108 A-l CH ₂OMe OEt 561

109 A-l CI, OMe OMe 568

110 A-3 OEt OEt 561

111 A-3 OEt OMe 547

112 A-l CH ₂CH ₂OH OMe 547

113 A-l CH ₂F OMe 535

114 A-l CH ₂CH ₂F OMe 549

115 A-l CH ₂CH ₂F OEt 563

116 A-l CH ₂CH ₂OH OEt 561

117 A-l OEt O-n-Bu 589

118 A-2 OEt OEt 583*

119 A-2 OMe OMe 555*

120 A-l OEt OCH ₂CH=CH ₂ 573

121 A-2 OEt OMe 569*

122 A-2 OMe OEt 569*

123 (Ex. 6) A-l OMe OCH ₂CH=CH ₂ **

124 A-l SMe OMe 549

125 A-l OEt OH 533

126 (Ex. 7) A-l OMe OH **

127 A-l OMe O-n-Pr 583*

128 A-l SMe OEt 585*

129 A-l CH ₂C1 OMe 551

130 A-l CH ₂OH OEt 547

131 A-l CH ₂C1 OEt 565

132 A-l OMe O-i-Bu 575

133 A-l SMe O-n-Pr 599*

134 A-l CH ₂SMe OMe 563

135 A-l CH ₂SEt OMe 577

136 A-l CH ₂SEt OEt 591

137 A-l CH ₂F OEt 549 Cmpd No. A R5 R4 N.M.R/M.S.

138 A-l CH ₂CH ₂Br OEt 623

139 A-l SMe 0-«-Bu 613*

140 A-l SEt OMe 585*

141 A-l SEt OEt 599*

142 (Ex. 9) A-l OMe NHOMe **

143 (Ex. 10) A-l OMe OCH ₂OMe **

144 (Ex. 8) A-l OMe O-c-Bu **

145 A-l SEt OCH ₂CH=CH ₂ 611*

146 A-l SEt OH 547[M-H]

147 A-l OMe OCH ₂(pyridine-4-yl) 610

149 A-l C0 ₂Et OEt 589

@ See Index Table G for ^lU HMR data. ** See synthesis example for !H NMR data.

* Mass spectra (i.e. M.S.) data reported as [M+Na].

INDEX TABLE B

Cmpd No. R ² R ⁵ R ⁴ M.S.

201 5-Me OMe OEt 561

202 5-Cl OMe OEt 581 Cmpd No. R2 R5 R4 M.S.

203 5-Cl OEt OEt 595

204 5-Me OEt OEt 575

205 3-OMe OMe OEt 577

206 5-Cl OMe OMe 567

207 5-Cl OEt OMe 581

211 5-Cl OMe 0-«-Bu 609

212 5-Cl OMe O-z-Pr 595

214 5-F OMe OMe 551

215 4-F OMe OMe 551

216 4-F OMe OEt 565

217 5-F OMe OEt 565

218 3 -Me OMe OMe 547

Cmpd No. R ² R ⁵ R ⁴ M.S.

208 5-OMe OEt OEt 591

209 5-OMe OMe OMe 563

210 5-OMe OMe OEt 577 213 5-OMe OEt OMe 577

Cmpd No. X2 Cmpd No. X2 R5 R4 M.S.

301 CI OMe OEt 563

302 N0 ₂ OMe OEt 574

INDEX TABLE G

Cmpd No. NMR Data (CDCI3 solution unless indicated otherwise) ^a

i 7.40 (d, IH), 7.30 (m, IH), 7.18 (m, 2H), 7.00 (m, IH), 6.80 (m, IH), 6.30 (d, IH), 6.01 and

5.85 (d, IH), 4.30 (q, 2H), 3.55 (s, 3H), 1.28 (t, 3H).

δ 7.38 (d, IH), 7.22 (d, IH), 7.14-7.00 (m, 3H), 6.75 (m, IH), 6.29 (s, IH), 5.48 (s, IH), 3.75 (s, 3H), 3.50 (s, 3H), 3.47 (s, 3H).

δ 7.40 (d, IH), 7.20 (d, IH), 7.10-6.98 (m, 3H), 6.75 (dd, IH), 6.27 (s, IH), 5.47 (s, IH), 4.23 (q, 2H), 3.5 (two s, 6H), 1.21 (t, 3H).

δ 7.90 (m, IH), 7.38 (m, IH), 7.23 (m, IH), 6.95-6.80 (m, 2H), 6.30 (s, IH), 6.18 (d, IH), 4,20

(q, 2H), 3.8-3.6 (m, 2H), 3.51 (s, 3H), 2.12 (m, 6H).

Cmpd. No. means Compound number. ^a NMR data are in ppm downlield from tetramethylsilane.

Couplings are designated by (s)-singlet, (m)-multiplet, (d)-doublet, (q)-quartet and (t)-triplet.

BIOLOGICAL EXAMPLES OF THE INVENTION

TEST A

Seeds of barnyardgrass {Echinochloa crus-galU), large crabgrass (crabgrass, lg; Digitaria sanguinalis), giant foxtail (foxtail, giant; Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time these species were also treated with postemergence applications of test compounds formulated in the same manner.

Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatments. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Table A Compounds

125 g ai/ha 1 2 6 7 10 11 12 13 14 15 16 17 18 19

Postemergence

Barnyardgrass 100 100 100 100 70 70 100 100 100 100 100 100 100 100

Corn 80 100 70 0 50 70 70 90 100 60 90 90 90 70

Crabgrass, Lg 100 100 100 80 70 70 70 100 100 100 100 100 100 100

Foxtail, Giant 100 100 100 100 70 80 70 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 60 90 70 50 70 70 60 80 100 100 90 90 80 90

Table A Compounds

125 g ai/ha 20 21 22 23 24 25 26 27 55 56 102 103 104 105

Postemergence

Barnyardgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 70

Corn 100 100 80 80 80 90 80 90 100 80 90 100 80 80

Crabgrass, Lg 100 100 100 100 100 100 100 100 100 100 100 90 100 60

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 50

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 70 80 90 70 80 90 70 90 80 80 50 60 90 50

Table A Compounds

125 g ai/ha 106 107 108 109 110 111 112 113 114 115 116 117 118 119

Postemergence

Barnyardgrass 100 90 100 0 100 90 100 100 100 100 100 100 100 100

Corn 70 80 80 0 70 80 80 90 80 60 60 60 90 90 Crabgrass, Lg 90 100 100 10 90 90 100 100 90 100 60 100 100 100

Foxtail, Giant 100 100 100 20 90 100 100 100 100 100 60 100 100 100

Morningglory 100 100 100 40 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 40 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 30 100 100 100 100 100 100 100 100 100 100

Wheat 60 50 90 0 60 60 50 100 60 50 50 60 90 80

Table A Compounds

125 g ai/ha 120 121 122 123 124 125 126 127 128 129 130 131 132 133

Postemergence

Barnyardgrass 100 100 100 100 100 100 100 100 100 100 100 100 80 100

Corn 100 90 100 100 30 60 100 80 50 60 70 70 70 70

Crabgrass, Lg 100 90 100 100 60 70 100 100 100 90 100 90 80 100

Foxtail, Giant 100 100 100 100 60 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 60 60 70 100 60 60 90 100 80 80 60 50 50 50

Table A Compounds

125 g ai/ha 134 135 136 137 138 139 140 141 148 149 150 151 152 153

Postemergence

Barnyardgrass 100 100 100 100 70 100 100 100 70 100 100 90 50 100

Corn 80 70 50 80 50 70 70 70 50 70 40 50 40 70

Crabgrass, Lg 90 80 70 90 80 90 90 100 70 100 100 80 70 90

Foxtail, Giant 100 90 90 100 80 100 100 100 80 100 100 80 60 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 60 60 60 80 50 40 50 50 60 70 60 50 40 50

Table A Compounds

125 g ai/ha 201 202 203 204 205 206 207 208 209 210 211 212 213 301

Postemergence

Barnyardgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 50

Corn 100 70 30 50 50 80 70 100 100 100 70 50 90 20

Crabgrass, Lg 100 70 60 60 70 100 60 60 70 70 100 90 90 40

Foxtail, Giant 100 100 100 50 90 100 100 80 100 80 100 100 100 20

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 70 60 40 50 80 60 50 70 90 90 60 70 70 30

Table A Compounds Table A Compounds

125 g ai/ha 302 401 402 125 g ai/ha 302 401 402

Postemergence Postemergence

Barnyardgrass 100 100 100 Morningglory 100 100 100

Corn 80 70 60 Pigweed 100 100 100

Crabgrass, Lg 70 50 100 Velvetleaf 100 100 100

Foxtail, Giant 100 60 100 Wheat 50 50 50

Table A Compounds

31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14

Postemergence

Barnyardgrass 100 100 100 100 100 90 60 60 90 50 50 60 100 100

Corn 40 90 80 80 50 30 0 50 60 40 30 30 50 50

Crabgrass, Lg 60 100 100 100 100 80 70 80 70 60 50 60 70 70

Foxtail, Giant 80 100 100 100 100 100 80 80 80 60 70 50 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 90 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 60 60 60 80 50 40 50 70 50 40 40 40 80

Table A Compounds

31 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28

Postemergence

Barnyardgrass 100 90 100 100 100 100 90 90 70 100 100 100 100 100

Corn 30 50 70 90 60 60 70 70 30 50 40 30 40 70

Crabgrass, Lg 60 100 90 90 80 80 70 100 70 80 80 70 90 100

Foxtail, Giant 70 100 100 100 100 100 100 100 100 100 100 90 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 50 50 50 50 50 40 60 40 50 50 50 60 60

Table A Compounds

31 g ai/ha 29 30 31 32 36 38 40 41 42 43 44 45 46 47

Postemergence

Barnyardgrass 100 100 50 100 90 100 100 100 80 100 90 100 100 100

Corn 50 80 80 50 50 40 100 50 20 80 100 70 90 80

Crabgrass, Lg 100 80 80 100 100 100 90 100 80 90 100 100 100 100 Foxtail, Giant 100 100 60 100 100 90 100 100 80 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 70 70 50 50 50 50 60 60 50 50 60 50 70 50

Table A Compounds

31 g ai/ha 48 49 50 51 52 55 56 60 61 62 63 64 65 66

Postemergence

Barnyardgrass 20 100 80 100 100 100 100 100 90 100 50 100 100 100

Corn 20 70 30 80 80 50 20 30 30 70 20 70 70 80

Crabgrass, Lg 50 100 70 100 100 80 80 100 100 100 50 100 100 100

Foxtail, Giant 60 100 100 100 100 100 100 - 100 100 50 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 90 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 50 40 50 50 50 50 40 50 50 30 60 50 60

Table A Compounds

31 g ai/ha 67 68 69 70 71 72 73 74 75 76 77 78 79 80

Postemergence

Barnyardgrass 100 80 90 100 80 80 90 100 100 100 60 100 100 100

Corn 70 70 90 80 60 50 60 60 70 50 30 80 50 70

Crabgrass, Lg 100 100 100 100 100 100 90 100 100 80 60 100 90 100

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 80 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 60 50 50 50 70 50 60 50 60 50 30 50 60 60

Table A Compounds

31 g ai/ha 81 82 83 84 85 86 87 88 89 90 91 92 93 94

Postemergence

Barnyardgrass 100 100 100 20 100 100 100 100 100 100 100 90 100 100

Corn 40 100 80 20 80 70 80 70 90 70 80 70 90 60

Crabgrass, Lg 80 100 90 40 100 100 100 90 100 100 100 90 100 100

Foxtail, Giant 100 100 100 50 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 80 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 40 50 60 20 60 50 70 50 60 50 50 50 60 60

Table A Compounds

31 g ai/ha 95 96 97 98 99 101 102 103 104 105 106 107 108 109

Postemergence

Barnyardgrass 100 100 90 40 20 80 100 100 90 30 60 70 100 0

Corn 80 100 50 20 30 70 50 40 50 40 50 50 40 0

Crabgrass, Lg 100 100 90 30 60 100 90 60 80 50 60 70 70 0

Foxtail, Giant 100 100 100 30 0 100 100 90 100 20 70 70 100 10

Morningglory 100 100 100 60 100 100 100 100 100 100 100 100 100 30

Pigweed 100 100 100 70 60 100 100 100 100 100 100 100 100 20

Velvetleaf 100 100 100 70 70 100 100 100 100 100 100 100 100 10

Wheat 50 60 50 30 40 50 40 40 50 30 40 40 50 0

Table A Compounds

31 g ai/ha 110 111 112 113 114 115 116 117 118 119 120 121 122 123

Postemergence

Barnyardgrass 50 50 100 90 90 100 100 100 80 80 100 90 100 100

Corn 40 20 40 30 50 40 50 40 30 40 50 40 60 50

Crabgrass, Lg 50 40 50 60 50 50 40 70 30 40 80 50 70 90

Foxtail, Giant 40 40 40 80 50 50 50 60 60 90 100 70 100 100

Morningglory 100 100 100 100 100 100 70 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 50 30 30 50 40 30 50 50 50 50 50 50 60

Table A Compounds

31 g ai/ha 124 125 126 127 128 129 130 131 132 133 134 135 136 137

Postemergence

Barnyardgrass 50 40 100 100 100 100 80 80 70 100 70 60 50 100

Corn 20 30 40 50 30 20 50 20 30 30 30 30 30 30

Crabgrass, Lg 30 40 70 80 70 60 60 60 60 70 60 50 50 70

Foxtail, Giant 40 60 100 100 80 60 100 60 70 70 60 50 50 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 90 80 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 30 40 70 50 50 50 40 40 40 30 50 50 50 70

Table A Compounds

31 g ai/ha 138 139 140 141 142 143 144 145 146 147 148 149 150 151

Postemergence Barnyardgrass 50 70 80 100 100 100 100 90 70 90 40 100 80 60

Corn 20 30 30 30 80 50 80 50 20 90 20 30 30 20

Crabgrass, Lg 60 60 60 60 90 100 100 80 70 80 50 70 90 50

Foxtail, Giant 50 70 90 70 100 100 100 90 70 100 50 100 90 60

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 90

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 30 30 30 50 60 60 40 50 50 40 40 40 30

Table A Compounds

31 g ai/ha 152 153 201 202 203 204 205 206 207 208 209 210 211 212

Postemergence

Barnyardgrass 20 100 100 90 90 50 70 100 90 70 50 50 100 100

Corn 30 20 40 30 20 20 20 50 40 50 60 60 30 30

Crabgrass, Lg 30 60 60 50 40 20 20 50 50 40 50 50 70 60

Foxtail, Giant 20 90 100 70 50 20 40 50 30 30 30 50 90 100

Morningglory 60 100 100 100 60 80 60 100 70 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 30 30 60 40 30 20 50 50 40 50 40 40 40 40

Table A Compounds

31 g ai/ha 213 214 215 216 217 301 302 401 402

Postemergence

Barnyardgrass 100 100 100 100 100 10 80 50 100

Corn 30 90 70 60 50 20 20 50 40

Crabgrass, Lg 50 100 90 90 90 10 50 40 80

Foxtail, Giant 40 100 100 100 100 10 50 50 90

Morningglory 100 100 100 100 100 100 100 80 100

Pigweed 100 100 100 100 100 80 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100

Wheat 40 60 60 60 60 10 30 40 40

Table A Compounds

16 g ai/ha 3 4 5 8 9 33 34 35 37 39 53 54 57 58

Postemergence

Barnyardgrass 100 100 100 50 50 50 20 20 0 60 60 0 10 10

Corn 70 70 40 30 30 10 10 10 0 20 20 10 10 0

Crabgrass, Lg 100 90 90 70 60 60 20 20 0 70 70 0 10 30

Foxtail, Giant 100 100 100 70 60 70 20 30 0 70 60 0 0 0 Morningglory 100 100 100 100 100 100 20 100 30 100 100 10 20 0

Pigweed 100 100 100 100 100 100 30 100 0 100 100 - 10 20

Velvetleaf 100 100 100 100 100 100 100 100 40 100 100 40 30 40

Wheat 60 60 60 50 40 30 0 10 0 20 20 0 0 0

Table A Compounds Table A Compounds

16 g ai/ha 59 100 218 16 g ai/ha 59 100 218

Postemergence Postemergence

Barnyardgrass 80 50 10 Morningglory 50 100 20

Corn 10 30 10 Pigweed 60 100 20

Crabgrass, Lg 20 60 0 Velvetleaf 90 100 50

Foxtail, Giant 50 60 10 Wheat 0 20 0

Table A Compounds

8 g ai/ha 3 4 5 8 9 28 29 30 31 32 36 38 40 41

Postemergence

Barnyardgrass 100 90 90 30 30 90 100 80 40 90 80 100 80 100

Corn 50 40 30 30 20 20 20 30 40 20 20 20 50 20

Crabgrass, Lg 90 80 70 60 60 70 60 60 60 80 80 80 70 70

Foxtail, Giant 100 100 90 70 50 80 80 80 50 90 80 80 100 80

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 50 50 40 40 40 30 50 50 40 30 30 30 40 30

Table A Compounds

8 g ai/ha 42 43 44 45 46 47 48 49 50 51 52 60 61 62

Postemergence

Barnyardgrass 60 80 70 100 100 90 20 80 50 100 90 60 80 100

Corn 20 40 30 30 40 40 20 30 30 40 60 20 20 30

Crabgrass, Lg 60 70 60 70 80 70 50 60 60 70 70 90 70 60

Foxtail, Giant 70 100 100 100 100 100 50 80 60 70 100 100 100 80

Morningglory 100 100 100 100 100 100 80 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 80 100 80 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 30 30 30 50 50 40 10 40 30 40 50 30 30 40

Table A Compounds

8 g ai/ha 63 64 65 66 67 68 69 70 71 72 73 74 75 76

Postemergence

Barnyardgrass 30 100 100 100 90 70 80 100 70 80 70 100 100 60 Corn 20 30 30 40 50 30 30 50 40 30 30 30 50 30

Crabgrass, Lg 10 70 80 60 60 60 80 70 70 70 70 70 80 60

Foxtail, Giant 20 100 100 90 80 70 100 80 80 80 100 100 90 70

Morningglory 60 100 100 100 100 100 90 100 100 100 100 100 100 100

Pigweed 70 100 100 100 100 100 100 100 100 100 100 100 100 80

Velvetleaf 70 100 100 100 90 100 100 100 100 100 100 100 100 100

Wheat 10 40 40 40 40 30 40 40 60 40 50 50 50 40

Table A Compounds

8 g ai/ha 77 78 79 80 81 82 83 84 85 86 87 88 89 90

Postemergence

Barnyardgrass 40 100 80 80 60 60 100 10 90 100 80 100 80 50

Corn 30 50 40 40 20 100 50 10 50 40 30 40 50 30

Crabgrass, Lg 30 70 70 70 60 70 80 10 70 70 70 60 70 70

Foxtail, Giant 40 80 100 100 70 100 80 20 90 80 80 60 100 70

Morningglory 100 100 100 100 100 100 80 70 100 100 100 100 100 100

Pigweed 100 100 90 100 100 100 100 70 100 100 100 100 100 80

Velvetleaf 100 100 100 100 100 100 100 70 100 100 100 100 100 100

Wheat 20 30 50 40 20 30 50 0 40 40 40 40 50 40

Table A Compounds

8 g ai/ha 91 92 93 94 95 96 97 98 99 101 142 143 144 145

Postemergence

Barnyardgrass 80 50 70 50 100 100 30 30 10 80 50 70 100 50

Corn 40 30 70 20 30 60 30 0 20 30 20 20 20 20

Crabgrass, Lg 80 60 70 60 60 80 70 20 0 60 70 70 70 60

Foxtail, Giant 90 70 90 70 90 90 90 10 0 80 90 90 100 70

Morningglory 100 100 100 100 100 100 100 30 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 - 0 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 30 60 100 100 100 100 100

Wheat 40 40 40 40 40 40 30 0 30 40 30 40 40 30

Table A Compounds

8 g ai/ha 146 147 214 215 216 217

Postemergence

Barnyardgrass 40 70 100 60 80 100

Corn 20 30 50 30 50 20

Crabgrass, Lg 50 70 60 70 60 60

Foxtail, Giant 40 80 80 80 100 100

Morningglory 100 100 100 100 100 100 Pigweed 100 100 100 100 90 100

Velvetleaf 100 100 100 100 100 100

Wheat 30 40 50 50 50 50

Table A Compounds

4 g ai/ha 3 4 5 8 9 33 34 35 37 39 53 54 57 58 Postemergence

Barnyardgrass 80 80 60 30 20 10 10 10 0 20 40 0 0 0 Corn 40 30 20 30 20 10 10 0 0 10 10 10 0 0

Crabgrass, Lg 90 70 60 50 50 40 0 10 0 40 50 0 0 20

Foxtail, Giant 90 90 90 60 40 50 10 10 0 30 40 0 0 0

Morningglory 100 100 100 100 100 100 0 30 0 100 60 0 0 0

Pigweed 100 100 100 100 100 100 20 100 0 100 100 0 0 0

Velvetleaf 100 100 100 100 100 100 100 100 30 100 100 10 20 20

Wheat 40 40 40 30 20 10 0 0 0 10 0 0 0 0

Table A Compounds Table A Compounds 4 g ai/ha 59 100 218 4 g ai/ha 59 100 218 Postemergence Postemergence

Barnyardgrass 0 40 0 Morningglory 0 40 0 Corn 10 20 10 Pigweed - 100 0

Crabgrass, Lg 20 50 0 Velvetleaf 60 100 30 Foxtail, Giant - 50 0 Wheat 0 0 0

Table A Compounds

125 g ai/ha 1 2 6 7 10 11 12 13 14 15 16 17 18 19

Preemergence

Barnyardgrass 70 80 80 70 40 70 60 90 100 100 100 90 90 100

Corn 0 60 20 0 0 30 90 50 70 60 60 20 50 50

Crabgrass, Lg 90 100 100 90 70 90 70 80 100 100 100 100 100 100

Foxtail, Giant 90 100 90 90 70 80 90 80 100 100 100 100 90 100

Morningglory 100 100 100 100 - 100 80 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 70 30 0 40 80 70 60 80 80 90 90 70 80

Table A Compounds

125 g ai/ha 20 21 22 23 24 25 26 27 55 56 102 103 104 105

Preemergence

Barnyardgrass 100 90 80 80 90 100 90 100 100 80 70 70 90 50

Corn 30 60 50 30 0 50 0 70 30 20 50 60 60 50 Crabgrass, Lg 100 90 100 100 100 100 100 100 100 100 100 100 100 70

Foxtail, Giant 100 90 100 100 100 100 100 100 100 100 80 100 100 80

Morningglory 90 100 100 100 100 100 100 90 100 100 80 100 100 10

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 90

Wheat 70 90 70 20 80 60 70 90 80 70 0 70 80 80

Table A Compounds

125 g ai/ha 106 107 108 109 110 111 112 113 114 115 116 117 118 119

Preemergence

Barnyardgrass 40 50 80 0 40 20 80 60 40 40 60 90 50 50

Corn 20 40 50 0 30 30 60 70 60 50 50 80 40 50

Crabgrass, Lg 70 90 90 0 50 40 100 100 100 90 80 90 80 80

Foxtail, Giant 70 80 90 0 60 60 90 80 90 70 70 80 80 100

Morningglory 100 100 100 0 100 100 100 100 100 100 100 100 100 100

Pigweed 100 100 100 0 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 10 100 100 100 100 100 100 100 100 100 100

Wheat 10 0 50 0 50 40 30 70 60 50 60 40 40 30

Table A Compounds

125 g ai/ha 120 121 122 123 124 125 126 127 128 129 130 131 132 133

Preemergence

Barnyardgrass 90 50 80 100 60 80 90 100 50 50 90 50 70 50

Corn 80 30 50 60 0 70 70 60 10 60 - 20 20 10

Crabgrass, Lg 100 60 90 100 70 100 100 100 70 70 100 20 100 80

Foxtail, Giant 90 80 100 100 70 80 100 100 70 70 90 60 90 90

Morningglory 100 80 100 100 60 80 100 100 100 100 70 50 70 80

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 70 100 100

Wheat 80 80 90 80 10 30 90 80 70 80 50 10 50 40

Table A Compounds

125 g ai/ha 134 135 136 137 138 139 140 141 148 149 150 151 152 153

Preemergence

Barnyardgrass 0 0 0 80 70 40 40 50 60 60 70 50 0 50

Corn 0 0 0 50 0 0 0 0 0 50 0 0 - 20

Crabgrass, Lg 40 0 50 90 100 80 80 80 90 100 90 80 10 80

Foxtail, Giant 60 30 60 100 90 80 70 70 90 90 90 70 20 70

Morningglory 50 0 0 100 70 90 70 70 70 80 40 40 20 100

Pigweed 100 90 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 70 100 60 100 100 100 100 100 100 100 100 100 60 100

Wheat 0 0 0 60 0 0 0 0 0 40 50 20 10 40

Table A Compounds

125 g ai/ha 201 202 203 204 205 206 207 208 209 210 211 212 213 301

Preemergence

Barnyardgrass 90 50 20 40 100 50 50 50 100 70 60 40 80 0

Corn 70 30 0 0 50 50 40 60 90 80 60 30 80 0

Crabgrass, Lg 80 70 60 60 100 90 60 100 100 100 70 60 70 0

Foxtail, Giant 100 70 20 80 100 100 70 100 100 100 100 90 100 0

Morningglory 100 60 60 60 60 90 90 100 100 100 90 70 100 40

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 50

Velvetleaf 100 100 100 80 100 100 100 100 100 100 100 100 100 50

Wheat 60 50 20 0 50 40 40 40 90 90 60 40 70 0

Table A Compounds Table A Compounds

125 g ai/ha 302 401 402 125 g ai/ha 302 401 402

Preemergence Preemergence

Barnyardgrass 50 70 90 Morningglory 70 100 100

Corn 0 60 60 Pigweed 100 100 100

Crabgrass, Lg 70 90 100 Velvetleaf 100 100 100

Foxtail, Giant 60 100 90 Wheat 0 70 50

Table A Compounds

31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14

Preemergence

Barnyardgrass 30 40 60 60 60 30 0 20 60 20 60 0 30 50

Corn 0 40 20 40 0 0 0 60 0 0 0 0 0 30

Crabgrass, Lg 80 90 90 90 90 80 70 80 80 40 60 10 10 60

Foxtail, Giant 70 90 80 70 70 70 40 90 90 50 60 30 40 80

Morningglory 100 100 100 90 40 60 30 0 50 0 - 60 50 100

Pigweed 100 100 100 90 100 100 100 100 100 100 - 80 100 100

Velvetleaf 60 80 100 90 100 50 100 100 100 100 100 80 80 100

Wheat 20 20 40 50 10 0 0 20 30 0 40 0 0 20

Table A Compounds

31 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28

Preemergence

Barnyardgrass 70 60 50 40 50 40 40 20 20 50 30 50 50 50

Corn 10 20 0 0 0 0 0 0 20 0 0 0 20 0

Crabgrass, Lg 90 90 70 80 60 70 60 90 80 70 80 100 80 90 Foxtail, Giant 80 80 80 80 70 70 60 90 70 70 70 70 80 80

Morningglory 100 80 80 40 50 90 40 60 70 100 80 60 80 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 50 10 0 30 0 40 40 30 0 20 0 0 40 40

Table A Compounds

31 g ai/ha 29 30 31 32 36 38 40 41 42 43 44 45 46 47

Preemergence

Barnyardgrass 70 70 50 40 60 60 50 60 40 50 50 30 70 50

Corn 10 10 0 0 10 0 10 10 10 0 10 0 0 0

Crabgrass, Lg 90 90 100 70 60 - 70 80 60 70 80 100 90 90

Foxtail, Giant 90 90 80 60 60 70 70 80 60 70 70 60 60 70

Morningglory 80 80 0 80 70 70 90 90 70 80 90 50 60 70

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 90 70 80 70 80 100 70 100 100 100 100

Wheat 40 50 0 20 20 10 20 30 10 30 30 0 0 0

Table A Compounds

31 g ai/ha 48 49 50 51 52 55 56 60 61 62 63 64 65 66

Preemergence

Barnyardgrass 10 20 0 50 50 50 10 50 60 10 0 50 50 20

Corn 0 0 0 0 0 0 0 0 20 0 0 0 0 0

Crabgrass, Lg 0 70 40 90 90 80 70 70 60 70 0 90 80 70

Foxtail, Giant 0 70 50 60 70 80 70 90 60 60 0 70 60 50

Morningglory 0 60 20 70 70 60 90 100 80 40 0 60 60 10

Pigweed 0 100 80 100 100 100 100 100 100 100 0 100 100 90

Velvetleaf 0 100 70 100 100 100 100 100 100 100 0 100 100 70

Wheat 0 0 0 0 0 50 0 0 20 0 0 0 0 0

Table A Compounds

31 g ai/ha 67 68 69 70 71 72 73 74 75 76 77 78 79 80

Preemergence

Barnyardgrass 50 40 60 60 50 40 50 40 50 50 0 30 40 50

Corn 0 0 0 0 20 0 0 0 0 10 0 0 0 0

Crabgrass, Lg 70 90 100 90 70 70 80 80 90 80 0 80 70 70

Foxtail, Giant 60 80 70 80 50 60 70 70 70 60 0 60 60 60

Morningglory 60 60 90 60 100 10 60 70 80 60 0 70 30 60

Pigweed 90 100 100 100 100 100 100 100 100 100 0 100 100 80

Velvetleaf 90 90 100 100 90 80 100 100 90 100 0 80 90 100 Wheat 0 0 0 0 10 20 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 81 82 83 84 85 86 87 88 89 90 91 92 93 94

Preemergence

Barnyardgrass 50 40 50 0 50 50 50 60 40 60 40 40 50 60

Corn 0 20 0 0 0 0 - 0 - 0 0 0 0 0

Crabgrass, Lg 60 70 70 0 90 90 90 80 80 70 90 70 70 90

Foxtail, Giant 40 60 60 0 70 60 80 70 70 60 70 60 70 70

Morningglory 30 40 80 0 50 40 80 60 90 20 30 70 60 100

Pigweed 80 100 100 0 100 100 80 100 100 80 100 100 100 100

Velvetleaf 70 80 90 0 100 90 100 70 80 70 90 100 100 100

Wheat 0 0 0 0 10 0 0 0 0 0 0 0 0 50

Table A Compounds

31 g ai/ha 95 96 97 98 99 101 102 103 104 105 106 107 108 109

Preemergence

Barnyardgrass 50 50 60 0 0 10 40 30 50 0 0 0 40 0

Corn 0 0 0 0 10 0 20 0 0 0 0 0 30 0

Crabgrass, Lg 70 70 80 0 50 - 50 70 60 0 10 60 50 0

Foxtail, Giant 70 60 50 0 0 50 50 60 50 0 20 40 40 0

Morningglory 70 60 60 0 30 20 70 60 70 10 100 - 70 0

Pigweed 100 100 100 0 60 100 100 100 100 90 100 90 100 0

Velvetleaf 100 90 100 30 0 100 80 100 100 70 50 60 100 0

Wheat 30 0 30 0 0 0 0 0 60 40 0 0 20 0

Table A Compounds

31 g ai/ha 110 111 112 113 114 115 116 117 118 119 120 121 122 123

Preemergence

Barnyardgrass 0 0 20 30 10 10 10 50 0 10 40 30 10 60

Corn - - - 10 0 0 0 50 0 20 50 0 0 10

Crabgrass, Lg 0 0 20 40 50 70 50 50 10 0 30 0 10 70

Foxtail, Giant 10 20 40 50 50 10 30 60 0 30 50 10 70 80

Morningglory 100 100 10 100 100 80 60 100 100 90 100 60 100 -

Pigweed 100 100 100 100 100 90 80 100 100 100 100 100 100 100

Velvetleaf 30 50 30 90 70 60 60 100 100 60 100 100 100 100

Wheat 0 20 0 0 30 20 30 0 20 0 30 40 0 60

Table A Compounds

31 g ai/ha 124 125 126 127 128 129 130 131 132 133 134 135 136 137

Preemergence Barnyardgrass 30 10 50 60 10 30 30 0 20 0 0 0 0 50

Corn 0 0 0 0 0 50 0 0 0 0 0 0 0 0

Crabgrass, Lg 10 60 50 70 10 0 40 0 70 60 0 0 0 80

Foxtail, Giant 0 20 80 70 10 10 50 0 60 10 0 0 0 70

Morningglory 0 50 70 100 30 70 50 30 50 70 0 0 0 70

Pigweed 100 100 100 100 100 100 100 80 100 100 100 80 60 100

Velvetleaf 60 60 100 100 80 80 70 40 60 100 0 20 30 100

Wheat 0 0 20 60 50 70 40 0 0 0 0 0 0 20

Table A Compounds

31 g ai/ha 138 139 140 141 142 143 144 145 146 147 148 149 150 151

Preemergence

Barnyardgrass 0 0 0 0 50 60 60 0 10 50 0 10 20 40

Corn 0 0 0 0 0 0 0 0 0 10 0 30 0 0

Crabgrass, Lg 60 30 10 30 90 90 100 0 30 70 50 80 70 50

Foxtail, Giant 70 40 10 10 60 90 90 30 30 70 40 60 60 50

Morningglory 50 10 0 10 80 80 70 20 0 80 40 60 - 0

Pigweed 100 100 90 80 100 100 100 100 - 100 100 100 100 100

Velvetleaf 80 80 30 0 100 100 100 60 40 100 100 100 50 100

Wheat 0 0 0 0 0 0 0 0 0 20 0 0 0 0

Table A Compounds

31 g ai/ha 152 153 201 202 203 204 205 206 207 208 209 210 211 212

Preemergence

Barnyardgrass 0 0 30 0 0 10 10 30 40 10 30 50 20 0

Corn 0 0 0 0 0 0 0 0 0 0 10 60 0 0

Crabgrass, Lg 0 0 10 10 0 10 20 30 40 30 60 40 30 20

Foxtail, Giant 0 30 20 10 0 30 50 30 10 50 90 90 50 40

Morningglory 0 50 100 10 0 0 10 50 30 60 60 100 20 10

Pigweed 20 100 - 100 80 80 70 100 100 100 100 100 100 90

Velvetleaf 10 50 80 60 50 60 60 80 70 100 100 100 100 50

Wheat 0 0 20 0 0 0 30 0 0 0 0 10 0 0

Table A Compounds

31 g ai/ha 213 214 215 216 217 301 302 401 402

Preemergence

Barnyardgrass 0 60 60 70 50 0 0 20 50

Corn 20 10 0 0 0 0 0 0 40

Crabgrass, Lg 20 70 70 70 80 0 0 40 90

Foxtail, Giant 70 80 70 70 70 0 0 20 70 Morningglory 80 90 70 100 100 0 60 60 90

Pigweed 100 100 90 100 100 0 100 100 100

Velvetleaf 100 100 100 100 100 0 70 40 100

Wheat 20 0 0 0 0 0 0 0 0

Table A Compounds

16 g ai/ha 3 4 5 8 9 33 34 35 37 39 53 54 57 58

Preemergence

Barnyardgrass 50 50 50 0 30 10 0 10 0 10 0 0 0 0

Corn 0 0 0 50 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 60 50 80 40 10 80 0 0 0 70 40 0 0 0

Foxtail, Giant 70 50 60 50 30 60 0 0 0 60 10 0 0 0

Morningglory 100 30 0 0 0 70 0 10 0 50 0 0 0 0

Pigweed 100 90 100 100 0 90 60 40 0 100 - 0 0 0

Velvetleaf 100 70 60 100 10 100 30 0 0 100 100 0 0 0

Wheat 30 40 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds Table A Compounds

16 g ai/ha 59 100 218 16 g ai/ha 59 100 218

Preemergence Preemergence

Barnyardgrass 0 0 0 Morningglory 0 0 70

Corn 0 0 0 Pigweed 0 100 0

Crabgrass, Lg 0 60 0 Velvetleaf 0 30 60

Foxtail, Giant 0 60 0 Wheat 0 0 0

Table A Compounds

8 g ai/ha 3 4 5 8 9 28 29 30 31 32 36 38 40 41

Preemergence

Barnyardgrass 10 30 10 0 0 10 20 20 0 0 20 10 0 10

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 50 30 60 - 0 70 30 60 70 40 0 10 50 10

Foxtail, Giant 60 0 60 0 0 60 10 60 30 20 40 40 40 10

Morningglory 100 0 0 0 - 40 30 60 0 50 10 50 40 10

Pigweed 100 90 100 100 0 60 100 100 90 100 60 100 100 80

Velvetleaf 50 40 0 50 0 80 60 80 60 10 30 50 40 0

Wheat 0 0 0 0 0 0 0 10 0 0 0 0 0 0

Table A Compounds

8 g ai/ha 42 43 44 45 46 47 48 49 50 51 52 60 61 62

Preemergence

Barnyardgrass 0 0 20 0 40 0 0 0 0 10 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 0 0 10 30 50 50 0 0 0 10 60 20 40 40

Foxtail, Giant 0 20 20 0 10 40 0 30 0 0 40 50 10 0

Morningglory 0 20 10 0 0 30 0 0 0 20 50 30 30 0

Pigweed 70 90 50 90 100 80 0 80 0 80 100 90 90 70

Velvetleaf 0 0 0 20 50 50 0 30 0 60 60 0 20 40

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

8 g ai/ha 63 64 65 66 67 68 69 70 71 72 73 74 75 76

Preemergence

Barnyardgrass 0 0 0 0 10 30 20 30 30 10 10 10 30 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 0 50 60 0 40 50 70 40 20 10 20 10 60 0

Foxtail, Giant 0 40 30 10 30 40 50 40 10 0 40 10 50 0

Morningglory 0 20 0 0 0 30 30 30 10 0 20 20 50 10

Pigweed 0 80 90 60 70 60 70 70 30 80 60 70 90 10

Velvetleaf 0 40 60 40 50 50 30 50 60 50 60 70 80 60

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

8 g ai/ha 77 78 79 80 81 82 83 84 85 86 87 88 89 90

Preemergence

Barnyardgrass 0 0 20 20 0 0 30 0 10 10 0 40 0 10

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 0 20 30 40 0 50 40 0 70 50 60 40 50 10

Foxtail, Giant 0 10 0 10 0 30 40 0 60 40 50 30 30 0

Morningglory 0 40 10 10 0 20 50 0 - 0 10 30 20 0

Pigweed 0 70 70 50 60 80 100 0 50 60 0 40 40 10

Velvetleaf 0 60 70 40 30 40 70 0 40 60 60 60 40 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

8 g ai/ha 91 92 93 94 95 96 97 98 99 101 142 143 144 145

Preemergence

Barnyardgrass 20 0 10 0 40 10 0 0 0 0 0 10 10 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 60 20 40 30 60 40 30 0 0 0 40 60 60 0

Foxtail, Giant 50 20 30 40 30 30 30 0 0 0 40 60 60 0

Morningglory 0 0 30 0 50 0 30 0 0 0 40 60 60 0 Pigweed 90 60 20 100 70 100 40 0 0 0 100 100 100 10

Velvetleaf 20 20 50 50 60 80 50 0 0 10 10 60 60 0

Wheat 0 0 0 20 0 0 0 0 0 0 0 0 0 0

Table A Compounds Table A Compounds

8 g ai/ha 146 147 214 215 216 217 8 g ai/ha 146 147 214 215 216 217

Preemergence Preemergence

Barnyardgrass 0 0 10 10 10 10 Morningglory 0 10 60 10 60 70

Corn 0 0 0 0 0 0 Pigweed 0 70 80 80 100 90

Crabgrass, Lg 0 0 50 40 10 30 Velvetleaf 0 0 60 40 70 50

Foxtail, Giant 0 20 40 50 30 50 Wheat 0 0 0 0 0 0

Table A Compounds

4 g ai/ha 3 4 5 8 9 33 34 35 37 39 53 54 57 58

Preemergence

Barnyardgrass 0 0 0 0 0 10 - 0 0 0 0 0 0 0

Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Crabgrass, Lg 0 20 0 - 0 60 0 0 0 50 20 0 0 0

Foxtail, Giant 40 0 50 0 0 40 0 0 0 50 0 0 0 0

Morningglory 10 0 0 0 0 20 0 0 0 30 0 0 0 0

Pigweed 90 70 80 30 0 90 - 0 0 70 0 0 0 0

Velvetleaf 40 20 0 0 0 80 - 0 0 30 10 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds Table A Compounds

4 g ai/ha 59 100 218 4 g ai/ha 59 100 218

Preemergence Preemergence

Barnyardgrass 0 0 0 Morningglory 0 0 10

Corn 0 0 0 Pigweed 0 - 0

Crabgrass, Lg 0 30 0 Velvetleaf 0 0 0

Foxtail, Giant 0 30 0 Wheat 0 0 0

TEST B

Seeds of plant species selected from blackgrass {Alopecurus myosuroides), downy bromegrass (bromegrass, downy; Bromus tectorum), green foxtail (foxtail, green; Setaria viridis), Italian ryegrass (ryegrass, Italian; Lolium multiflorum), wheat (Triticum aestivum), wild oat (oat, wild; Avena fatua), catchweed bedstraw (gallium; Galium aparine), bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), large crabgrass (crabgrass, lg; Digitaria sanguinalis), woolly cupgrass (cupgrass, woolly; Eriochloa villosa), giant foxtail (foxtail, giant; Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nightshade (Solarium ptycanthum), yellow nutsedge (nutsedge, yellow; Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (Ambrosia elatior), soybean (Glycine max), common (oilseed) sunflower (sunflower; Helianthus annuus), velvetleaf (Abutilon theophrasti) and Russian thistle (Salsola kali) were planted into a blend of loam soil and sand and treated preemergence with test compounds formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also winter barley (barley; Hordeum vulgare), canarygrass (Phalaris minor), chickweed (Stellaria media), henbit deadnettle (deadnettle; Lamium amplexicaule), and windgrass (Apera spica- venti) were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Plant species in the flooded paddy test consisted of rice (Oryza sativa), umbrella sedge (sedge, umbrella; Cyperus difformis), duck salad (ducksalad; Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At the time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test.

Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Table B Compounds

250 g ai/ha 6 16 27 113 124 125 130 131 132 149 150 211 212 213

Flood

Barnyardgrass 75 100 100 30 20 0 100 85 100 65 95 85 80 0

Ducksalad 100 100 100 80 100 100 100 100 100 100 100 100 100 100

Rice 85 100 100 40 35 30 90 40 45 90 80 35 45 50

Sedge, Umbrella 100 100 100 65 80 80 100 100 100 100 100 100 100 100

Table B Compounds

125 g ai/ha 1 2 13 15 17 18 19 20 28 29 30 32 33 34

Flood

Barnyardgrass 65 30 40 40 85 70 80 95 60 80 70 75 65 0

Ducksalad 95 85 100 100 100 100 100 100 100 100 95 100 100 0

Rice 50 35 35 40 60 75 80 75 60 80 50 60 80 0

Sedge, Umbrella 100 100 65 90 100 100 100 100 100 100 95 100 100 0 Table B Compounds

125 g ai/ha 35 36 37 38 39 40 41 42 43 44 45 46 47 48

Flood

Barnyardgrass 65 45 0 100 85 55 40 35 80 100 50 50 40 20

Ducksalad 85 100 0 100 100 100 100 100 100 100 100 100 100 75

Rice 30 75 0 85 50 95 65 40 65 100 70 70 70 65

Sedge, Umbrella 65 95 0 100 100 100 100 100 100 100 100 100 100 50

Table B Compounds

125 g ai/ha 49 50 51 52 53 54 55 57 58 59 60 61 62 63

Flood

Barnyardgrass 85 0 30 65 40 0 70 0 0 0 75 100 40 0

Ducksalad 100 70 100 100 100 0 100 0 0 0 100 100 100 0

Rice 95 30 45 45 45 0 75 0 0 0 80 100 65 0

Sedge, Umbrella 100 70 95 100 100 0 100 0 0 0 100 100 100 0

Table B Compounds

125 g ai/ha 64 65 66 67 68 69 70 71 72 73 74 77 79 80

Flood

Barnyardgrass 65 60 45 15 20 45 25 45 20 40 30 30 30 45

Ducksalad 100 100 100 100 100 100 100 - 90 70 - 80 80 100

Rice 75 50 40 20 30 40 40 35 20 40 25 5 30 65

Sedge, Umbrella 100 100 100 85 75 100 100 80 20 85 65 75 70 100

Table B Compounds

125 g ai/ha 81 82 84 85 86 87 88 89 90 91 94 98 99 100

Flood

Barnyardgrass 60 0 0 60 25 0 0 20 30 30 60 40 15 85

Ducksalad - - 65 100 100 100 - - - 100 100 80 80 100

Rice 50 35 15 45 45 30 30 40 35 45 45 60 15 60

Sedge, Umbrella 95 60 65 100 60 85 95 85 90 100 100 100 85 100

Table B Compounds

125 g ai/ha 101 104 105 110 111 112 113 122 123 124 125 126 127 128

Flood

Barnyardgrass 75 75 0 20 0 0 25 20 40 0 0 40 0 65

Ducksalad 100 100 60 80 85 100 70 100 100 75 75 100 0 100

Rice 70 75 55 30 25 45 30 40 60 30 30 50 0 70

Sedge, Umbrella 100 100 80 60 60 60 40 95 100 40 0 100 0 85 Table B Compounds

125 g ai/ha 130 131 132 133 134 135 136 137 141 142 143 144 145 146 Flood

Barnyardgrass 50 70 45 65 25 0 20 30 55 50 70 80 35 20

Ducksalad 100 90 100 100 90 30 80 100 100 100 100 100 90 70

Rice 45 45 45 75 35 30 35 40 60 90 80 60 35 20

Sedge, Umbrella 90 100 100 100 90 0 75 100 100 100 100 100 90 30

Table B Compounds

125 g ai/ha 147 149 151 152 153 201 202 203 204 205 206 207 208 209 Flood

Barnyardgrass 50 45 65 20 40 0 60 20 0 0 0 0 0 0

Ducksalad 100 100 100 85 100 80 100 50 0 0 60 30 40 40

Rice 60 60 70 30 45 40 60 30 0 0 0 0 0 0

Sedge, Umbrella 100 100 100 65 100 95 100 80 0 0 50 0 0 0

Table B Compounds Table B Compounds

125 g ai/ha 210 218 125 g ai/ha 210 218

Flood Flood

Barnyardgrass 0 0 Rice 30 0

Ducksalad 65 0 Sedge, Umbrella 0 0

Table B Compounds

62 g ai/ha 1 2 4 5 6 7 8 12 13 14 15 16 17 18 Flood

Barnyardgrass 40 0 0 15 55 20 25 0 30 0 30 40 40 30

Ducksalad 85 50 100 100 100 80 100 80 95 40 100 100 100 100

Rice 35 30 20 40 75 35 50 40 30 0 30 40 45 45

Sedge, Umbrella 95 65 85 80 100 80 95 65 0 0 65 98 100 100

Table B Compounds

62 g ai/ha 19 20 27 28 29 30 32 33 34 35 36 37 38 39 Flood

Barnyardgrass 50 30 50 25 40 20 60 30 0 0 40 0 80 30

Ducksalad 100 100 100 100 90 90 100 100 0 0 100 0 100 100

Rice 70 70 30 40 35 25 50 45 0 0 40 0 70 30

Sedge, Umbrella 100 100 100 95 70 70 100 75 0 0 80 0 85 85

Table B Compounds

62 g ai/ha 40 41 42 43 44 45 46 47 48 49 50 51 52 53 Flood Barnyardgrass 50 30 30 30 100 40 30 0 0 75 0 15 40 30

Ducksalad 100 100 100 100 100 100 100 100 75 100 40 100 100 100

Rice 20 40 20 43 90 50 50 45 40 40 25 30 25 20

Sedge, Umbrella 80 95 85 100 100 100 100 80 0 80 50 80 100 65

Table B Compounds

62 g ai/ha 54 55 57 58 59 60 61 62 63 64 65 66 67 68

Flood

Barnyardgrass 0 45 0 0 0 40 80 30 0 30 20 15 15 15

Ducksalad 0 95 0 0 0 100 100 100 0 100 100 85 90 85

Rice 0 50 0 0 0 40 85 40 0 40 30 30 20 20

Sedge, Umbrella 0 95 0 0 0 80 100 90 0 80 85 80 40 40

Table B Compounds

62 g ai/ha 69 70 71 72 73 74 77 79 80 81 82 84 85 86

Flood

Barnyardgrass 20 20 0 10 20 15 15 20 30 20 0 0 25 20

Ducksalad 100 100 - - - - 60 - 100 - - 40 100 95

Rice 15 30 25 20 30 15 5 15 30 25 20 0 30 30

Sedge, Umbrella 80 30 80 0 0 65 40 50 80 85 20 65 90 0

Table B Compounds

62 g ai/ha 87 88 89 90 91 94 98 99 100 101 102 104 105 106

Flood

Barnyardgrass 0 0 10 20 20 60 30 15 0 0 25 65 0 15

Ducksalad 85 90 - 100 100 100 75 0 75 95 95 95 0 100

Rice 20 20 20 20 35 35 50 10 40 45 40 70 45 40

Sedge, Umbrella 0 60 80 60 90 75 0 0 80 95 65 95 60 95

Table B Compounds

62 g ai/ha 107 108 109 110 111 112 113 118 119 122 123 124 125 126

Flood

Barnyardgrass 0 0 0 20 0 0 0 0 0 0 0 0 0 30

Ducksalad 100 70 75 60 30 70 0 65 85 75 100 20 0 100

Rice 40 30 10 20 10 25 30 30 30 40 50 20 0 40

Sedge, Umbrella 65 60 75 55 0 40 0 60 60 60 80 0 0 75

Table B Compounds

62 g ai/ha 127 128 130 131 132 133 134 135 136 137 141 142 143 144

Flood

Barnyardgrass 0 30 40 20 20 60 25 0 15 25 30 40 60 30 Ducksalad 0 90 85 85 80 100 85 0 80 80 85 80 100 100

Rice 0 45 30 30 40 40 25 20 20 40 35 50 40 25

Sedge, Umbrella 0 75 80 85 90 100 85 0 40 70 85 70 80 95

Table B Compounds

62 g ai/ha 145 146 147 148 149 150 152 153 201 202 203 204 205 206

Flood

Barnyardgrass 20 20 40 15 0 70 0 30 0 30 15 0 0 0

Ducksalad 70 70 100 95 100 100 50 85 60 60 20 0 0 0

Rice 25 20 20 45 30 50 30 35 30 40 25 0 0 0

Sedge, Umbrella 70 30 80 85 95 100 50 60 0 70 40 0 0 0

Table B Compounds

62 g ai/ha 207 208 209 210 211 212 213 218

Flood

Barnyardgrass 0 0 0 0 40 40 0 0

Ducksalad 0 30 0 0 80 85 95 0

Rice 0 0 0 0 35 35 30 0

Sedge, Umbrella 0 0 0 0 45 80 65 0

Table B Compounds

31 g ai/ha 1 4 5 7 8 9 10 11 12 13 14 15 17 18

Flood

Barnyardgrass 20 0 0 0 20 20 0 0 0 20 0 0 30 0

Ducksalad 65 80 75 60 85 95 0 0 60 90 0 75 95 100

Rice 0 20 35 25 30 5 0 0 30 20 0 20 45 20

Sedge, Umbrella 0 30 45 70 95 95 0 0 65 0 0 50 90 100

Table B Compounds

31 g ai/ha 19 20 28 29 30 32 33 34 35 36 37 38 39 40

Flood

Barnyardgrass 20 20 30 20 15 40 0 0 0 35 0 60 20 40

Ducksalad 95 90 90 90 90 95 100 0 0 100 0 100 85 100

Rice 25 30 20 20 15 45 30 0 0 20 0 70 25 0

Sedge, Umbrella 85 70 30 60 50 75 0 0 0 90 0 75 60 70

Table B Compounds

31 g ai/ha 45 46 47 48 49 50 52 53 54 55 57 58 59 60

Flood

Barnyardgrass 20 20 0 0 0 0 0 0 0 30 0 0 0 20

Ducksalad 90 85 100 40 80 0 100 60 0 85 0 0 0 80 Rice 40 30 30 0 30 20 20 15 0 20 0 0 0 40

Sedge, Umbrella 60 75 60 0 20 50 75 40 0 75 0 0 0 50

Table B Compounds

31 g ai/ha 62 63 64 65 66 77 84 94 98 99 100 101 102 104

Flood

Barnyardgrass 20 0 20 20 10 0 0 15 0 0 0 0 0 30

Ducksalad 90 0 75 85 60 0 40 100 0 0 20 60 85 85

Rice 30 0 20 20 25 5 0 20 20 0 15 25 30 25

Sedge, Umbrella 30 0 65 80 75 0 0 30 0 0 20 60 50 85

Table B Compounds

31 g ai/ha 105 106 107 109 110 111 112 113 118 119 122 123 124 125

Flood

Barnyardgrass 0 0 0 0 20 0 0 0 0 0 0 0 0 0

Ducksalad 0 100 75 40 60 0 40 0 0 60 0 100 0 0

Rice 0 25 25 0 15 0 0 20 20 0 20 30 0 0

Sedge, Umbrella 40 85 55 70 40 0 30 0 0 50 40 75 0 0

Table B Compounds

31 g ai/ha 126 127 128 130 131 132 134 135 136 137 141 142 143 144

Flood

Barnyardgrass 20 0 10 40 10 0 0 0 0 20 20 40 20 0

Ducksalad 85 0 65 80 80 85 40 0 20 55 80 70 85 100

Rice 30 0 40 20 25 30 0 0 0 30 20 30 20 20

Sedge, Umbrella 65 0 40 80 65 0 50 0 0 45 40 30 70 20

Table B Compounds

31 g ai/ha 145 146 147 148 149 151 152 153 201 202 203 204 205 206

Flood

Barnyardgrass 20 10 30 0 0 20 0 0 0 0 0 0 0 0

Ducksalad 0 0 100 30 85 95 0 70 50 30 0 0 0 0

Rice 10 10 15 20 20 0 0 20 15 20 20 0 0 0

Sedge, Umbrella 10 0 75 60 70 65 0 50 0 0 30 0 0 0

Table B Compounds

31 g ai/ha 207 208 209 210 218

Flood

Barnyardgrass 0 0 0 0 0

Ducksalad 0 0 0 0 0

Rice 0 0 0 0 0 Sedge, Umbrella 0 0 0 0 0

Table B Compounds

16 g ai/ha 1 4 5 7 8 12 13 14 15 17 18 19 20 28

Flood

Barnyardgrass 0 0 0 0 0 0 0 0 0 20 0 10 0 30

Ducksalad 0 0 0 50 65 0 0 0 0 75 70 80 60 85

Rice 0 0 20 20 20 0 0 0 0 35 20 20 20 0

Sedge, Umbrella 0 0 0 70 60 50 0 0 0 50 70 30 0 20

Table B Compounds

16 g ai/ha 29 30 32 33 34 35 36 37 38 39 40 45 46 47

Flood

Barnyardgrass 15 10 30 0 0 0 30 0 60 20 40 20 0 0

Ducksalad 80 75 90 70 0 0 100 0 85 50 85 40 60 75

Rice 10 10 30 30 0 0 10 0 15 25 0 30 20 20

Sedge, Umbrella 0 15 0 0 0 0 60 0 60 80 60 50 60 0

Table B Compounds

16 g ai/ha 48 49 50 52 53 54 55 57 58 59 60 62 63 64

Flood

Barnyardgrass 0 0 0 0 0 0 10 0 0 0 0 15 0 20

Ducksalad 0 0 0 75 0 0 40 0 0 0 60 0 0 50

Rice 0 25 15 20 0 0 15 0 0 0 10 30 0 20

Sedge, Umbrella 0 0 0 70 0 0 0 0 0 0 0 20 0 50

Table B Compounds

16 g ai/ha 65 66 77 84 94 98 99 100 101 102 104 105 106 107

Flood

Barnyardgrass 20 10 0 0 15 0 0 0 0 0 10 0 0 0

Ducksalad 70 45 0 40 75 0 0 20 40 0 30 0 65 65

Rice 15 20 5 0 10 15 0 0 20 15 20 0 0 0

Sedge, Umbrella 60 70 0 - 0 0 0 0 0 30 20 0 40 25

Table B Compounds

16 g ai/ha 108 109 110 Ill 112 118 119 122 123 126 127 128 134 135

Flood

Barnyardgrass 0 0 20 0 0 0 0 0 0 0 0 10 0 0

Ducksalad 40 65 0 0 20 0 0 0 80 80 0 0 0 0

Rice 0 0 0 0 0 10 0 10 20 10 0 20 0 0

Sedge, Umbrella 40 70 30 0 0 0 30 0 0 0 0 20 0 0 Table B Compounds

16 g ai/ha 136 137 141 142 143 144 145 146 147 152 153 201 202 203

Flood

Barnyardgrass 0 0 10 20 20 0 0 0 0 0 0 0 0 0

Ducksalad 20 30 40 70 85 100 0 0 85 0 60 0 0 0

Rice 0 20 15 15 20 15 0 0 15 0 0 10 0 0

Sedge, Umbrella 0 35 30 0 0 0 0 0 70 0 0 0 0 0

Table B Compounds

16 g ai/ha 204 205 206 207 208 209 210 218

Flood

Barnyardgrass 0 0 0 0 0 0 0 0

Ducksalad 0 0 0 0 0 0 0 0

Rice 0 0 0 0 0 0 0 0

Sedge, Umbrella 0 0 0 0 0 0 0 0

Table B Compounds

8 g ai/ha 4 5 7 8 12 14 102 106 107 109 118 119

Flood

Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0

Ducksalad 0 0 40 0 0 0 0 0 60 75 0 0

Rice 0 15 10 10 0 0 15 0 0 0 0 0

Sedge, Umbrella 0 0 70 0 50 0 0 0 0 70 0 0

Table B Compound Table B Compound

62 g ai/ha 149 62 g ai/ha 149

Postemergence Postemergence

Bermudagrass 98 Kochia 100

Chickweed 100 Lambsquarters 100

Cocklebur 100 Morningglory 100

Corn 100 Nutsedge, Yellow 20

Crabgrass, Lg 100 Pigweed 100

Cupgrass, Woolly 100 Ragweed 100

Foxtail, Giant 100 Soybean 100

Goosegrass 75 Surinam Grass 100

Johnsongrass 100 Velvetleaf 100

Table B Compounds

31 g ai/ha 6 7 13 14 15 16 17 18 Postemergence

Barley 35 100 55 60 100 100 85 80 100 100 100 100 100 Bermudagrass 70 100 100 98 100 100 98 75 100 98 100 100 100 100

Blackgrass - - - 80 85 70 70 75 100 100 100 100 100 90

Bromegrass, Downy 60 85 85 90 90 100 65 55 100 100 100 100 75 100

Canarygrass - 90 55 60 100 100 98 70 100 100 - - 100 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 0 100

Cocklebur - - 100 100 100 100 100 100 100 100 100 - 0 100

Corn 55 100 100 100 100 100 100 20 100 100 100 100 0 100

Crabgrass, Lg 100 100 100 100 100 100 90 60 100 100 100 100 35 98

Cupgrass, Woolly 100 100 100 100 100 100 100 70 100 100 100 100 0 100

Deadnettle - - - - - - 30 85 100 100 85 100 100 80

Foxtail, Giant 100 100 100 100 100 100 100 70 100 100 100 100 35 100

Foxtail, Green 100 100 100 100 100 100 100 85 100 65 100 100 100 100

Galium - - - - - - 100 100 100 100 - 100 100 100

Goosegrass 75 100 98 90 100 100 65 75 100 100 100 100 0 100

Johnsongrass 70 100 80 75 100 100 100 95 100 100 100 100 0 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 55 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 45 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 60 100

Nutsedge, Yellow 10 30 10 10 20 15 15 0 45 75 15 25 0 25

Oat, Wild 75 100 100 100 100 100 80 70 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 85 100

Ragweed 75 100 100 100 100 100 90 100 100 100 100 100 40 100

Ryegrass, Italian 60 100 100 100 80 100 45 60 100 95 100 85 70 80

Soybean 100 100 100 100 100 100 90 100 100 100 100 100 0 100

Surinam Grass 100 100 100 100 100 100 30 60 100 100 100 100 40 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 75 100

Wheat 50 100 100 100 100 100 80 50 100 100 100 100 100 100

Windgrass 65 100 100 100 100 100 50 100 100 85 85 100 100 85

Table B Compounds

31 g ai/ha 19 20 21 22 23 24 25 26 27 28 29 30 31 32

Postemergence

Barley 100 100 85 100 100 100 100 100 100 100 100 85 80 85

Bermudagrass 98 100 98 98 100 100 100 - 100 100 100 95 98 100

Blackgrass 90 100 100 100 90 100 100 85 100 90 80 85 65 100

Bromegrass, Downy 100 100 100 100 100 100 100 100 100 80 100 90 80 100

Canarygrass 100 100 100 100 100 100 100 100 - 100 100 100 75 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 100 100 100 100 100 - - 100 100 100 100 100 Corn 100 100 100 100 100 100 100 100 100 100 100 100 45 100

Crabgrass, Lg 100 100 100 100 100 100 100 100 100 100 100 100 65 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 98 100

Deadnettle 75 100 100 80 90 90 95 60 100 65 55 60 70 80

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 65 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 95 100

Galium 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Goosegrass 100 100 100 100 100 100 100 98 100 100 100 95 85 98

Johnsongrass 100 100 100 100 100 100 100 - 100 95 100 100 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 20 0 30 25 10 10 0 0 25 0 15 0 0 25

Oat, Wild 100 100 100 100 90 100 100 85 100 80 100 100 60 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 98 100 100

Ryegrass, Italian 100 100 85 80 85 85 80 85 100 70 70 70 50 80

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 98 100 100 100 100 65 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 100 95 100 100 55 100

Windgrass 98 100 98 90 90 85 100 100 100 80 85 85 65 100

Table B Compounds

31 g ai/ha 33 35 36 38 39 40 41 42 43 44 45 46 47 49

Postemergence

Barley 100 100 100 90 100 100 100 100 100 100 - 100 100 100

Bermudagrass 85 100 100 100 100 100 100 100 100 100 98 100 100 98

Blackgrass 85 85 100 80 100 80 85 85 85 65 70 90 85 100

Bromegrass, Downy 80 85 98 100 85 100 85 100 85 85 85 100 100 85

Canarygrass 100 100 100 100 100 100 100 100 100 100 85 100 100 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 - 100 100 100 100 - - 100 100 100 100 100 -

Corn 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Crabgrass, Lg 98 100 100 100 100 100 100 100 100 100 90 98 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 80 - 90 90 80 80 70 80 80 85 - 95 100 85

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Galium 100 100 100 100 100 100 100 80 100 100 100 100 100 100

Goosegrass 85 100 100 100 100 98 98 98 98 95 98 100 98 85

Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 40 0 45 10 20 20 45 15 15 5 0 20 10 20

Oat, Wild 90 85 100 100 100 100 100 85 100 90 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 80 70 100 85 85 100 60 85 85 65 50 75 70 60

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 100 100 70 100 100 100

Windgrass 85 80 100 85 100 100 - 80 100 85 75 100 100 80

Table B Compounds

31 g ai/ha 50 51 52 53 55 56 62 64 65 66 67 70 77 80

Postemergence

Barley 85 100 100 75 100 100 100 100 100 100 100 85 100 85

Bermudagrass 98 100 100 95 100 100 100 98 100 100 98 90 100 100

Blackgrass 85 100 100 85 100 100 80 100 80 100 100 85 100 100

Bromegrass, Downy 100 100 100 100 80 85 85 100 100 100 85 100 100 100

Canarygrass 100 100 100 98 100 100 100 100 100 100 100 100 100 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 - 100 - 100 - 100 100 100 100 - - 100 -

Corn 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Crabgrass, Lg 98 100 100 100 100 100 90 90 100 100 100 100 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 100 80 100 98 85 85 85 - 100 90 85 90 85 65

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Galium 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Goosegrass 100 98 95 100 100 100 95 100 100 85 98 98 95 85

Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Nutsedge, Yellow 10 0 - 20 0 5 10 10 - 0 0 0 20 0

Oat, Wild 100 100 100 100 100 100 85 100 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 60 100 90 70 85 - 40 80 70 70 80 100 - 100

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 - - 100 100

Wheat 100 100 100 100 100 100 80 100 100 100 100 100 100 100

Windgrass 100 100 100 85 100 100 70 100 100 100 100 100 65 100

Table B Compounds

31 g ai/ha 81 85 86 88 90 91 94 100 101 102 103 104 108 113

Postemergence

Barley 100 80 98 98 95 80 98 100 100 100 100 100 100 100

Bermudagrass 98 95 98 - 98 100 100 60 100 100 85 100 100 90

Blackgrass - 100 100 100 85 90 85 55 85 65 100 100 65 85

Bromegrass, Downy 100 100 100 85 100 100 100 50 100 100 100 100 100 100

Canarygrass 100 100 100 100 100 100 100 60 70 100 100 75 75 85

Chickweed 100 100 100 100 100 100 100 80 100 100 100 100 100 100

Cocklebur - 100 - 100 100 - 100 95 100 100 - 100 100 100

Corn 100 100 100 100 100 100 100 40 100 100 100 100 100 100

Crabgrass, Lg 100 100 100 100 100 100 98 45 85 100 100 100 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 45 100 100 100 100 100 100

Deadnettle 80 100 100 80 100 90 70 98 100 - 85 100 - 100

Foxtail, Giant 100 100 100 100 100 100 100 60 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 80 100 100 100 100 100 100

Galium 100 100 100 100 100 100 100 100 100 - 70 80 - 85

Goosegrass 90 100 85 95 98 100 95 70 95 100 95 100 95 90

Johnsongrass 98 100 100 100 100 100 100 60 100 100 100 100 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 - 100

Nutsedge, Yellow 0 0 0 0 0 0 10 0 10 40 15 20 15 50

Oat, Wild 100 100 100 100 100 100 100 60 100 85 - 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 80 85 80 80 100 100 75 45 80 60 80 70 100 100

Soybean 100 100 100 100 100 100 100 100 100 95 100 100 100 100 Surinam Grass 100 100 100 100 100 100 100 55 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 35 100 100 100 100 100 100

Windgrass 100 100 100 100 100 100 85 65 100 90 100 100 98 100

Table B Compounds

31 g ai/ha 119 120 122 123 125 126 127 128 130 137 140 141 142 143

Postemergence

Barley 100 100 100 100 85 100 100 100 100 98 100 100 80 100

Bermudagrass 85 75 98 100 100 75 100 85 98 100 98 95 98 100

Blackgrass 100 85 100 100 90 100 100 85 80 90 80 85 85 100

Bromegrass, Downy 100 100 100 100 90 100 100 100 65 100 80 85 55 100

Canarygrass 100 70 50 80 100 100 100 100 100 100 100 100 100 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 100 - 100 100 100 100 100 100 100 100 100 100

Corn 100 100 100 100 100 100 100 100 70 100 100 100 100 100

Crabgrass, Lg 100 100 100 100 100 100 100 100 95 100 98 100 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 100 - - 100 70 100 80 100 100 80 60 100 65 55

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 50 100 100 - 100 100 100 100 100 100 100 100

Galium 100 60 100 100 100 100 100 70 70 100 - 100 100 100

Goosegrass 98 85 85 100 100 90 100 85 85 100 95 80 95 100

Johnsongrass 100 100 100 100 100 100 100 100 100 100 98 100 80 100

Kochia 100 80 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 55 50 65 45 20 40 40 20 10 20 10 5 0 10

Oat, Wild 100 85 100 85 100 100 100 100 80 100 80 85 100 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 - 100 100 100 100 70 100 100 100 100 100

Ryegrass, Italian 100 85 100 98 80 100 100 70 40 100 60 45 70 98

Soybean 100 100 100 100 100 100 100 95 85 100 95 85 100 100

Surinam Grass 100 100 100 100 100 100 100 100 60 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Windgrass 100 75 80 85 100 90 100 80 80 90 65 80 - 100 Table B Compounds

31 g ai/ha 144 146 147 149 150 153 201 211 212 214 215 216 217 402

Postemergence

Barley 100 65 98 - 100 - 100 100 100 100 85 100 90 35

Bermudagrass 100 98 100 85 100 90 50 100 60 95 100 100 98 100

Blackgrass 100 80 85 - 70 70 100 100 90 85 98 85 80 60

Bromegrass, Downy 100 100 100 - 90 80 100 100 100 100 100 98 - 70

Canarygrass 100 85 100 - 100 80 60 100 80 100 100 100 100 60

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 - 100 100 100 100 - - 100 100 100 100 100

Corn 100 100 100 100 100 100 100 100 100 100 100 100 100 65

Crabgrass, Lg 100 98 100 100 100 100 95 100 90 100 100 90 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 100 80 60 - - 100 100 85 85 90 85 75 - -

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 - 100 100 45 100 90 100 100 100 100 100

Galium 100 80 100 - - 100 80 90 70 100 100 100 100 -

Goosegrass 98 75 100 70 100 75 95 98 65 100 90 100 100 90

Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Kochia 100 100 100 100 100 100 50 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 15 15 15 60 45 15 15 45 0 0 0 10

Oat, Wild 85 90 100 - 100 100 100 100 100 85 85 100 100 90

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 98

Ryegrass, Italian 100 70 50 - 80 70 65 50 45 80 85 - 80 80

Soybean 100 95 100 100 100 100 100 100 90 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 95 65 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 - 100 60 100 100 100 100 100 100 100 45

Windgrass 100 - 80 - 100 100 75 80 75 90 100 - - 100

Table B Compounds

16 g ai/ha 1 2 3 4 5 6 7 9 13 14 15 16 17 18

Postemergence

Barley 35 - 50 60 - 100 80 50 100 100 100 100 100 100

Bermudagrass 15 100 100 98 100 100 95 70 100 98 98 98 100 100

Blackgrass - 60 60 70 80 65 60 70 100 100 75 85 85 85 Bromegrass, Downy - 80 85 90 90 100 50 40 100 100 100 100 70 90

Canarygrass - - 50 55 100 100 80 60 100 100 - 85 100 100

Chickweed 100 100 100 100 100 100 98 95 100 100 100 100 0 100

Cocklebur - 100 100 100 100 100 100 100 100 100 100 - 0 100

Corn 40 100 100 100 100 100 90 20 100 100 100 100 0 100

Crabgrass, Lg 80 100 98 100 100 100 80 45 100 100 98 100 20 98

Cupgrass, Woolly 100 100 100 100 100 100 50 25 100 100 100 100 0 100

Deadnettle - - - - - - 30 80 100 100 80 85 100 80

Foxtail, Giant 100 100 100 100 100 100 100 50 100 100 100 100 20 100

Foxtail, Green 100 100 100 100 100 100 100 85 100 40 100 100 100 100

Galium - - - - - - 70 100 85 70 100 85 100 -

Goosegrass 70 100 90 85 100 100 55 60 95 100 98 100 0 98

Johnsongrass 65 100 70 70 100 100 90 85 100 100 100 100 0 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 55 100

Lambsquarters 100 100 100 100 100 100 95 100 100 100 100 100 45 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 50 100

Nutsedge, Yellow 10 15 10 10 20 15 5 0 45 60 15 20 0 10

Oat, Wild 65 100 100 100 100 100 80 70 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 85 100

Ragweed 75 100 100 100 100 100 70 100 100 100 100 100 40 100

Ryegrass, Italian 40 100 100 100 70 80 35 45 80 95 70 85 70 70

Soybean 98 100 100 100 100 95 80 100 100 100 100 100 0 100

Surinam Grass 75 100 100 100 100 100 25 40 100 100 100 100 5 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 45 100

Wheat 50 100 100 100 100 100 50 45 100 100 100 100 100 100

Windgrass 60 90 85 100 100 100 50 70 100 85 85 100 100 85

Table B Compounds

16 g ai/ha 19 20 21 22 23 24 25 26 27 28 29 30 31 32

Postemergence

Barley 85 100 80 100 100 90 100 100 100 85 100 85 60 85

Bermudagrass 98 100 98 95 98 100 100 - 98 98 100 80 75 100

Blackgrass 90 100 85 85 85 100 85 85 100 85 75 85 65 100

Bromegrass, Downy 85 80 100 98 85 85 100 85 100 80 100 70 60 100

Canarygrass 100 100 100 100 100 100 100 100 - 100 100 100 75 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 100 100 100 100 100 - - 100 100 100 100 100

Corn 100 100 100 100 100 100 100 100 100 100 100 100 30 100

Crabgrass, Lg 100 100 100 95 98 100 100 100 100 100 100 98 40 100 Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 85 100

Deadnettle 75 75 60 55 80 85 95 50 100 55 50 55 70 60

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 60 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 85 100

Galium 100 100 100 100 80 100 100 100 80 100 100 100 85 100

Goosegrass 100 100 100 100 100 100 100 95 100 85 95 85 75 95

Johnsongrass 95 100 100 98 100 100 100 - 100 85 100 100 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 5 0 25 5 10 5 0 0 20 0 5 0 0 25

Oat, Wild 100 100 100 100 90 100 100 85 100 75 100 80 55 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 98 100 100

Ryegrass, Italian 80 70 80 80 60 65 80 70 80 65 70 60 50 80

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 90 100 100 100 100 65 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 100 90 80 85 50 100

Windgrass 80 85 70 90 85 75 100 80 98 70 85 65 65 100

Table B Compounds

16 g ai/ha 33 35 36 38 39 40 41 42 43 44 45 46 47 49

Postemergence

Barley 85 85 100 85 100 100 100 98 100 85 100 85 70 100

Bermudagrass 85 100 98 100 85 100 100 100 100 100 98 100 100 75

Blackgrass 80 85 100 80 75 80 85 85 80 65 55 80 80 100

Bromegrass, Downy 60 85 85 100 70 100 85 60 70 85 55 100 100 80

Canarygrass 100 100 100 100 100 100 100 100 100 100 85 85 100 85

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 100 100 - 100 100 - 100 100 100 100 100 -

Corn 100 100 100 100 100 100 100 100 100 100 85 100 100 100

Crabgrass, Lg 95 100 85 85 80 85 100 100 100 100 80 95 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 60 65 70 70 70 65 60 70 50 85 100 75 80 85

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 80 100 100 100

Galium 100 100 100 100 100 100 100 80 100 100 100 100 100 100

Goosegrass 80 100 90 80 100 98 95 80 90 75 85 100 90 70 Johnsongrass 100 100 100 100 95 100 100 100 100 100 100 100 85 98

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 - 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 30 0 25 10 20 15 45 10 15 5 0 5 5 10

Oat, Wild 70 75 100 100 100 90 100 85 100 80 85 100 100 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 65 65 100 60 60 85 60 60 70 60 50 70 70 30

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 95

Surinam Grass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 85 100 100 100 85 100 100 60 100 100 100

Windgrass 75 60 100 75 85 100 100 50 80 85 50 100 100 50

Table B Compounds

16 g ai/ha 50 51 52 53 55 56 62 64 65 66 67 70 77 80

Postemergence

Barley 85 85 85 75 100 100 100 100 100 85 100 80 100 85

Bermudagrass 98 98 90 85 100 100 98 98 98 100 75 85 100 95

Blackgrass 85 80 100 85 100 100 60 80 80 100 100 80 100 100

Bromegrass, Downy 100 100 75 100 80 70 85 100 100 85 85 100 100 100

Canarygrass 100 100 100 95 100 100 75 100 100 100 85 100 70 85

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 - 100 - 100 - 100 100 100 100 - - 100 -

Corn 100 100 100 100 98 98 100 100 100 100 100 100 100 100

Crabgrass, Lg 95 95 90 100 100 100 85 90 98 100 100 100 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle - - 80 45 75 85 85 98 80 90 80 80 85 65

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Galium 100 100 100 100 85 100 100 100 100 100 100 100 100 100

Goosegrass 100 95 90 100 100 98 80 100 100 80 85 80 85 80

Johnsongrass 100 100 100 100 100 100 100 100 100 100 90 85 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 10 0 10 0 0 0 0 5 5 0 0 0 10 0

Oat, Wild 100 100 90 90 100 100 85 100 100 100 85 100 100 100 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 55 85 60 60 85 75 40 60 50 70 60 80 50 55

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 - - 100 100

Wheat 98 100 75 98 100 100 60 80 100 85 100 100 100 100

Windgrass 100 100 80 85 70 85 70 85 85 100 85 100 60 80

Table B Compounds

16 g ai/ha 81 85 86 88 90 91 94 100 101 102 103 104 108 113

Postemergence

Barley 98 80 - 75 95 80 98 100 100 100 100 100 100 100

Bermudagrass 95 85 - 98 95 100 85 60 100 90 80 98 100 55

Blackgrass 98 100 100 80 80 90 80 50 80 65 100 100 65 85

Bromegrass, Downy 100 100 100 85 100 80 90 50 45 100 100 100 100 100

Canarygrass 80 - 80 100 100 100 85 55 70 100 85 75 70 85

Chickweed 100 98 100 100 100 100 100 70 100 100 100 - 100 100

Cocklebur - 100 100 100 - - 100 90 100 100 - 100 100 100

Corn 100 100 100 100 100 100 100 20 65 100 100 100 100 100

Crabgrass, Lg 100 95 85 100 98 100 85 20 80 100 95 95 100 100

Cupgrass, Woolly 100 100 100 100 100 100 100 10 100 100 100 100 100 100

Deadnettle 80 65 80 80 100 80 55 50 80 - 85 80 - 90

Foxtail, Giant 100 100 100 100 100 100 100 45 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 70 100 100 100 100 100 80

Galium 100 100 100 100 100 100 100 100 100 - 70 70 - 85

Goosegrass 80 95 80 75 85 90 85 65 75 100 85 95 95 45

Johnsongrass 80 100 100 100 98 100 100 25 100 100 100 100 100 100

Kochia 98 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 - 100

Nutsedge, Yellow 0 0 0 0 0 0 10 0 10 15 15 10 15 45

Oat, Wild 85 100 100 100 100 100 70 60 100 85 - 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 95 65 100 100 100 100 100 100

Ryegrass, Italian 60 85 70 60 85 70 75 40 80 60 50 70 80 80

Soybean 100 100 100 100 100 100 100 85 100 80 95 100 100 100

Surinam Grass 100 100 100 100 100 100 100 45 100 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 100 100 100 100 100 100 85 30 100 100 100 100 100 100

Windgrass 80 85 100 85 100 100 80 55 85 80 80 85 80 100

Table B Compounds

16 g ai/ha 119 120 122 123 125 126 127 128 130 137 140 141 142 143

Postemergence

Barley 100 100 100 100 85 100 100 100 85 85 85 80 70 100

Bermudagrass 75 75 98 98 100 65 90 75 85 100 95 95 98 98

Blackgrass 100 85 85 100 85 85 100 85 65 80 70 70 85 85

Bromegrass, Downy 100 100 100 100 85 100 95 80 60 100 60 60 50 100

Canarygrass 100 70 50 80 100 - 100 80 60 100 85 80 85 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 - 100 - 100 100 100 100 100 100 100 100 100 100

Corn 100 98 100 100 100 100 100 98 20 100 100 100 100 100

Crabgrass, Lg 100 100 98 100 100 100 100 100 85 100 95 98 100 98

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 100 - - 100 70 100 80 70 80 70 60 100 65 55

Foxtail, Giant 100 100 100 100 100 100 100 100 98 100 100 98 100 100

Foxtail, Green 55 80 45 45 100 80 100 100 100 100 100 100 100 100

Galium 80 60 98 100 80 100 100 50 60 100 100 75 100 100

Goosegrass 85 85 85 98 100 70 90 65 75 100 75 75 80 90

Johnsongrass 100 100 100 100 98 100 100 100 100 95 85 100 75 98

Kochia 100 80 98 98 100 100 100 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 45 30 20 35 10 40 25 10 10 15 5 5 0 0

Oat, Wild 100 85 100 85 100 100 100 100 80 95 70 70 80 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 - 100 100 100 100 65 100 100 100 100 100

Ryegrass, Italian 80 60 70 75 70 55 90 50 35 65 45 35 70 85

Soybean 100 90 100 100 90 100 100 90 80 100 85 70 100 100

Surinam Grass 100 100 100 100 100 100 100 95 45 95 100 98 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 100 100 85 98 100 98

Windgrass 95 75 80 80 70 70 85 65 60 90 65 65 80 100

Table B Compounds

16 g ai/ha 144 146 147 149 150 153 201 211 212 214 215 216 217 402

Postemergence Barley 100 65 - - 100 100 98 100 100 100 85 100 90 35

Bermudagrass 98 25 100 75 100 60 20 98 50 90 98 85 95 100

Blackgrass 90 65 85 - 50 50 85 80 60 85 60 80 70 -

Bromegrass, Downy 90 85 100 - 90 70 100 100 100 80 100 85 100 70

Canarygrass 100 65 100 - 55 55 50 70 70 100 100 100 100 -

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cocklebur 100 100 - 100 100 100 100 - - 100 100 100 100 -

Corn 95 95 100 75 85 100 100 100 100 100 98 100 100 60

Crabgrass, Lg 98 75 100 95 100 100 85 98 90 100 100 90 85 80

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 55

Deadnettle 100 75 60 - - 100 100 85 85 90 65 60 70 -

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 98 100 - 100 65 40 65 80 100 100 100 100 100

Galium 100 65 100 - - 60 60 70 70 100 98 100 100 -

Goosegrass 95 55 100 70 100 45 80 98 60 100 85 95 100 75

Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Kochia 100 100 100 100 100 100 20 100 100 100 100 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 15 10 15 60 10 15 10 0 0 0 0 10

Oat, Wild 85 85 100 - 100 100 60 100 - 85 85 85 100 60

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 80 100 100 100 100 100 100 100 100 100 80

Ryegrass, Italian 70 60 50 - 60 55 60 45 40 75 60 70 60 50

Soybean 100 75 100 100 100 95 100 100 80 100 80 85 100 80

Surinam Grass 100 85 100 100 100 100 85 95 65 100 100 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 98 100 - 100 60 100 100 100 100 100 90 100 45

Windgrass 100 70 80 - 100 80 50 65 75 85 60 85 80 80

Table B Compounds

8 g ai/ha 1 2 3 4 5 6 7 9 13 14 15 16 17 18

Postemergence

Barley 35 100 40 60 100 100 70 50 100 100 100 100 100 85

Bermudagrass 5 100 100 95 100 95 90 65 85 75 75 85 100 100

Blackgrass 30 55 50 65 70 60 35 70 85 100 75 85 85 80

Bromegrass, Downy 50 80 60 90 80 70 45 40 100 100 100 100 60 85

Canarygrass 50 65 40 55 100 100 60 45 80 100 60 65 100 100

Chickweed 98 100 100 100 100 100 85 80 100 100 100 100 0 100 Cocklebur 45 - 100 100 100 100 100 100 100 100 100 - 0 100

Corn 25 95 100 100 100 100 20 15 90 100 95 100 0 100

Crabgrass, Lg 75 100 85 90 100 100 50 35 100 100 95 98 10 85

Cupgrass, Woolly 100 100 100 100 100 100 20 10 100 100 100 98 0 100

Deadnettle - - - - - - 30 70 98 - 80 85 80 60

Foxtail, Giant 100 100 100 100 100 100 85 35 100 100 100 100 10 100

Foxtail, Green 100 100 100 100 100 100 50 80 55 40 85 100 100 100

Galium - - - - - - 50 100 60 40 80 75 75 -

Goosegrass 10 100 85 85 100 100 45 60 85 75 90 85 0 90

Johnsongrass 60 100 65 70 100 100 75 55 100 100 100 100 0 100

Kochia 100 100 100 100 100 100 98 100 100 - 100 100 0 100

Lambsquarters 100 100 100 100 100 100 45 98 100 100 100 100 0 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 0 100

Nutsedge, Yellow 10 10 10 5 15 10 0 0 40 50 15 15 0 10

Oat, Wild 60 95 100 100 75 85 50 40 100 100 100 100 100 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 75 100

Ragweed 70 100 95 100 100 100 20 100 100 100 100 100 35 98

Ryegrass, Italian 30 95 70 70 70 75 10 30 75 70 60 60 35 70

Soybean 80 100 100 98 100 95 70 95 100 100 100 100 0 100

Surinam Grass 70 100 100 100 100 100 20 10 100 100 75 95 0 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 45 100

Wheat 45 80 85 100 100 85 35 40 100 100 100 100 100 90

Windgrass 55 80 75 90 100 80 40 45 100 70 80 85 50 70

Table B Compounds

8 g ai/ha 19 20 21 22 23 24 25 26 27 28 29 30 31 32

Postemergence

Barley 85 85 80 98 100 90 100 100 100 80 100 75 50 85

Bermudagrass 98 100 98 95 98 100 100 - 90 90 85 80 65 95

Blackgrass 85 100 80 75 85 85 80 75 85 80 70 65 55 70

Bromegrass, Downy 85 60 80 65 85 70 50 80 100 80 100 50 45 100

Canarygrass 100 100 100 100 100 100 100 100 100 85 85 80 55 100

Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 85 100

Cocklebur 100 100 100 100 100 100 100 - - 100 100 100 100 100

Corn 85 100 100 95 95 98 100 100 100 100 100 90 20 100

Crabgrass, Lg 100 100 98 95 98 100 100 100 98 98 98 95 20 100

Cupgrass, Woolly 100 100 100 100 100 100 100 100 98 100 100 100 15 100

Deadnettle 50 70 60 55 80 65 80 50 85 55 50 50 70 50

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 50 100 Foxtail, Green 100 100 100 100 100 100 100 100 100 100 100 100 70 100

Galium 100 100 100 98 75 100 80 - 80 100 100 100 85 100

Goosegrass 100 100 98 90 100 100 100 95 85 80 80 80 65 85

Johnsongrass 85 100 100 90 100 100 100 - 100 80 80 100 90 100

Kochia 100 100 100 100 100 100 100 100 100 100 98 100 100 85

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 75 100

Nutsedge, Yellow 5 0 25 5 5 0 0 0 20 0 5 0 0 25

Oat, Wild 85 100 100 100 85 100 100 85 100 70 75 70 55 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 95 100 100

Ryegrass, Italian 80 70 55 50 55 60 60 60 60 55 65 60 40 80

Soybean 100 100 100 100 100 100 100 100 100 100 100 100 95 100

Surinam Grass 100 100 100 100 100 100 100 85 95 100 100 100 55 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 90 100 100 85 100 85 80 70 50 100

Windgrass 80 80 70 50 85 70 80 60 80 45 80 60 60 100

Table B Compounds

8 g ai/ha 33 35 36 38 39 40 41 42 43 44 45 46 47 49

Postemergence

Barley 60 60 100 85 100 100 100 85 100 60 100 - 70 80

Bermudagrass 80 98 95 98 85 100 98 65 85 75 75 95 85 75

Blackgrass 60 65 80 65 70 80 75 60 75 60 50 80 80 85

Bromegrass, Downy 60 60 85 100 60 85 50 50 70 30 55 85 100 50

Canarygrass 85 65 100 100 100 100 100 80 100 85 60 85 75 45

Chickweed 100 100 98 100 100 100 100 100 98 100 100 98 98 100

Cocklebur 100 100 100 100 - 100 100 - 100 100 100 100 100 100

Corn 100 98 95 100 100 100 100 85 100 100 45 100 100 100

Crabgrass, Lg 95 98 80 85 80 80 80 80 85 98 80 85 90 80

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 95

Deadnettle 45 65 60 70 50 50 55 55 40 60 85 75 80 85

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 100 100 100 100 90 100 100 80 100 100 100

Galium 100 100 100 100 100 100 100 65 100 100 50 100 - -

Goosegrass 65 55 65 75 65 80 80 75 65 70 70 95 85 65

Johnsongrass 100 100 100 100 95 100 100 98 100 - 100 100 85 65

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Lambsquarters 98 100 100 100 100 100 100 - 100 100 100 100 100 100 Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 10 0 20 10 10 10 10 10 15 5 0 5 5 5

Oat, Wild 60 60 60 90 90 80 80 60 80 80 50 100 100 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 - 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 50 60 60 60 60 60 40 50 50 45 30 50 45 30

Soybean 100 100 100 100 100 100 100 100 100 100 95 100 100 80

Surinam Grass 95 100 95 100 100 100 100 85 100 95 85 100 100 100

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 98 60 100 85 100 100 100 85 100 85 45 100 100 100

Windgrass 70 55 80 75 80 80 70 50 80 60 50 80 60 50

Table B Compounds

8 g ai/ha 50 51 52 53 55 56 62 64 65 66 67 70 77 80

Postemergence

Barley 85 85 85 70 80 100 80 100 70 85 80 70 100 80

Bermudagrass 98 85 85 85 100 100 90 98 80 98 70 80 90 95

Blackgrass 80 80 75 60 75 70 60 80 60 100 70 80 70 60

Bromegrass, Downy 85 85 70 70 70 65 60 85 100 85 85 100 100 50

Canarygrass 100 100 100 70 100 100 50 100 80 100 80 100 70 80

Chickweed 100 100 100 100 100 100 100 100 100 95 98 100 100 100

Cocklebur 100 - 100 100 100 - 100 100 100 100 - - 100 100

Corn 100 100 100 100 95 90 65 100 100 100 65 100 100 98

Crabgrass, Lg 95 85 85 85 100 98 85 85 80 100 80 100 80 95

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Deadnettle 100 65 80 40 70 70 80 70 70 80 70 65 85 60

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Foxtail, Green 100 100 100 85 100 100 85 100 100 100 100 100 100 100

Galium 100 100 100 100 80 100 100 100 - 100 100 100 100 100

Goosegrass 98 75 80 80 98 98 70 100 80 70 70 75 75 80

Johnsongrass 100 80 100 100 100 98 100 100 100 100 80 70 100 100

Kochia 100 100 100 100 100 100 100 100 100 100 100 100 100 85

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 10 0 5 0 0 0 0 0 5 0 0 0 10 0

Oat, Wild 100 85 75 75 100 75 85 100 90 85 85 100 100 70

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, Italian 50 85 50 60 60 45 30 45 45 70 60 80 40 55 Soybean 100 100 100 100 100 98 90 100 100 100 100 100 95 85

Surinam Grass 100 100 100 100 100 80 100 100 85 100 100 100 100 98

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 98 100 - 80 100 100 40 80 50 50 100 100 100 100

Windgrass 90 85 75 60 70 50 50 80 60 70 60 85 55 70

Table B Compounds

8 g ai/ha 81 85 86 88 90 91 94 100 101 102 103 104 108 113

Postemergence

Barley 50 60 80 70 85 80 85 55 100 100 100 100 100 100

Bermudagrass 80 - 90 95 60 65 85 60 75 45 45 85 100 55

Blackgrass 40 100 100 70 70 80 75 45 80 60 55 100 45 65

Bromegrass, Downy 60 80 80 85 70 80 85 45 40 100 95 100 100 100

Canarygrass 70 100 80 80 100 100 85 50 35 100 55 60 60 65

Chickweed 98 98 90 100 95 100 100 60 95 100 100 - 100 100

Cocklebur 100 100 100 100 100 100 100 45 100 100 - 100 100 100

Corn 75 100 100 90 98 100 100 15 45 100 100 100 100 80

Crabgrass, Lg 90 80 80 100 95 80 85 10 75 95 80 95 80 100

Cupgrass, Woolly 100 100 100 100 100 100 100 10 100 100 98 100 100 100

Deadnettle - - 80 80 60 65 50 50 80 - 80 80 - 60

Foxtail, Giant 100 100 100 100 100 100 100 40 100 100 100 100 100 100

Foxtail, Green 75 100 100 100 100 100 85 70 100 100 80 100 70 45

Galium - 100 100 100 100 100 100 100 100 - 50 50 - 55

Goosegrass 75 90 75 75 85 75 80 60 60 85 80 85 75 45

Johnsongrass 75 98 100 98 85 75 80 0 100 100 60 100 100 80

Kochia 90 98 100 95 100 100 100 100 100 100 55 100 100 100

Lambsquarters 100 80 98 100 100 98 98 100 100 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 - 100

Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 10 15 10 10 35

Oat, Wild 75 100 100 80 80 100 70 50 80 85 100 100 80 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 95 45 100 100 100 100 100 100

Ryegrass, Italian 60 70 55 55 60 60 60 15 35 55 45 50 65 60

Soybean 98 98 100 100 100 100 100 85 90 80 65 90 80 100

Surinam Grass 100 100 100 98 100 100 90 30 100 100 98 98 100 85

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 100 100 100 100 100 100 80 30 100 100 100 100 85 65

Windgrass 65 85 75 70 80 85 80 50 60 65 70 65 75 65 Table B Compounds

8 g ai/ha 119 120 122 123 125 126 127 128 130 137 140 141 142 143

Postemergence

Barley 100 100 100 100 80 100 100 100 60 85 80 80 65 100

Bermudagrass 65 65 10 35 100 40 85 45 60 100 95 75 80 90

Blackgrass 100 75 85 60 75 85 - 65 65 80 70 60 75 70

Bromegrass, Downy 80 70 55 100 85 80 65 80 50 80 55 60 50 70

Canarygrass 65 50 40 80 90 100 85 80 50 85 80 80 80 100

Chickweed 100 10 80 100 100 100 100 100 100 100 100 100 100 98

Cocklebur 100 - 100 - 100 100 100 100 80 100 100 100 100 100

Corn 100 95 80 98 100 98 100 50 15 95 90 85 100 100

Crabgrass, Lg 100 85 60 75 100 70 100 95 85 95 95 75 85 98

Cupgrass, Woolly 100 100 100 100 100 100 100 100 20 100 100 100 100 100

Deadnettle 50 - - 95 55 - 80 70 70 65 50 80 60 50

Foxtail, Giant 100 100 85 100 100 100 100 100 80 100 100 98 100 100

Foxtail, Green 50 55 30 40 100 55 100 100 80 100 80 100 100 100

Galium 60 - 60 100 70 100 70 50 50 - 70 70 100 100

Goosegrass 45 50 20 60 100 60 85 25 65 98 75 50 75 85

Johnsongrass 100 100 100 100 85 100 100 100 95 95 85 100 75 98

Kochia 100 75 85 45 100 100 100 100 100 100 100 98 100 100

Lambsquarters 100 98 100 100 100 100 100 100 100 100 100 100 100 98

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 45 25 20 0 10 40 25 0 10 10 5 5 0 0

Oat, Wild 100 65 60 85 100 55 100 80 60 85 60 70 80 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 - 98 100 100 100 60 100 100 100 95 90

Ryegrass, Italian 70 40 55 50 50 55 60 40 35 65 45 30 60 60

Soybean 100 80 100 100 90 100 100 80 80 100 75 65 100 100

Surinam Grass 100 100 100 100 100 100 100 80 25 85 75 75 100 100

Velvetleaf 100 100 100 100 100 100 100 100 95 100 100 100 100 100

Wheat 100 100 100 100 100 100 100 100 50 100 80 80 70 70

Windgrass 90 25 65 55 45 70 60 60 45 85 60 60 70 75

Table B Compounds

8 g ai/ha 144 146 147 149 150 153 201 211 212 214 215 216 217 402

Postemergence

Barley 100 60 98 - 60 60 80 100 100 100 - 85 85 35

Bermudagrass 98 5 98 25 98 10 10 90 15 90 65 80 85 100

Blackgrass 80 55 70 - 45 35 45 45 60 65 60 65 55 20 Bromegrass, Downy 85 85 85 - 80 50 85 60 60 75 80 80 80 65

Canarygrass 100 55 100 - 50 55 45 40 60 100 100 100 80 20

Chickweed 100 20 100 70 100 100 45 100 90 100 98 100 100 100

Cocklebur 100 100 - 100 100 100 100 - - 100 55 100 100 65

Corn 95 65 100 15 70 85 95 100 80 100 98 98 100 60

Crabgrass, Lg 95 15 98 80 95 100 65 95 50 98 90 85 85 80

Cupgrass, Woolly 100 98 100 100 100 100 95 100 85 100 100 100 100 55

Deadnettle 70 50 50 - - 98 100 80 80 85 65 55 60 -

Foxtail, Giant 100 80 100 100 100 70 70 100 80 100 100 100 100 65

Foxtail, Green 100 85 100 - 100 40 15 50 45 100 100 100 100 100

Galium 100 65 100 - - 60 60 55 70 100 80 100 100 -

Goosegrass 95 10 85 55 100 10 65 90 10 90 65 80 100 70

Johnsongrass 100 100 100 100 100 100 75 100 75 100 100 100 100 65

Kochia 100 100 100 100 100 100 10 100 100 100 100 100 100 100

Lambsquarters 100 85 100 98 100 100 45 100 80 100 100 100 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 10 10 15 55 10 15 10 0 0 0 0 10

Oat, Wild 85 70 85 - 85 100 60 50 100 70 85 60 80 60

Pigweed 100 100 100 60 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 80 100 95 100 100 100 100 100 90 100 75

Ryegrass, Italian 60 45 50 - 55 50 55 40 40 60 55 45 55 50

Soybean 100 60 100 100 95 90 80 100 75 100 75 85 98 75

Surinam Grass 90 55 100 85 100 100 70 90 60 100 80 100 100 100

Velvetleaf 100 100 100 70 100 100 100 100 100 100 100 100 100 100

Wheat 100 75 100 - 80 55 100 80 100 100 100 85 65 40

Windgrass 60 10 80 - 80 60 50 50 50 70 60 80 60 60

Table B Compounds

4 g ai/ha 1 2 3 4 5 6 7 9 13 14 15 16 17 18

Postemergence

Barley 30 80 35 40 80 80 70 40 98 100 100 100 85 80

Bermudagrass 5 100 90 85 100 90 80 5 45 55 10 75 98 100

Blackgrass 30 55 30 50 50 55 15 40 55 55 45 85 80 80

Bromegrass, Downy 20 20 60 70 80 55 20 40 85 80 100 100 50 80

Canarygrass 50 50 25 20 100 85 50 45 60 70 60 60 80 85

Chickweed 70 100 100 100 100 65 5 5 98 100 100 98 0 98

Cocklebur - 100 100 100 100 100 40 90 100 100 100 - 0 100

Corn 25 45 100 98 100 100 20 15 85 100 75 65 0 90

Crabgrass, Lg 60 100 80 75 98 75 10 35 100 100 70 90 0 85 Cupgrass, Woolly 65 100 100 100 100 100 20 10 100 100 100 98 0 100

Deadnettle - - - - - - 15 60 60 70 70 85 65 55

Foxtail, Giant 65 100 95 100 100 100 65 10 100 100 98 100 0 100

Foxtail, Green 80 100 85 100 100 100 50 60 35 40 80 100 90 85

Galium - - - - - - 50 80 60 40 80 50 60 100

Goosegrass 10 100 75 85 98 75 15 55 25 50 85 60 0 90

Johnsongrass 55 100 65 65 100 100 5 40 100 75 100 100 0 85

Kochia 100 100 100 100 100 100 80 98 100 - 100 100 0 98

Lambsquarters 98 100 100 100 100 95 15 90 100 100 100 100 0 100

Morningglory 100 70 100 100 100 100 10 100 100 100 100 100 0 100

Nutsedge, Yellow 5 10 10 5 10 10 0 0 40 50 15 10 0 5

Oat, Wild 50 50 75 80 70 75 40 40 85 100 80 70 80 100

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 55 100

Ragweed 70 100 80 85 100 95 10 65 100 100 100 100 0 95

Ryegrass, Italian 30 10 60 60 60 55 5 25 45 60 30 45 35 50

Soybean 70 85 100 85 100 80 70 65 85 100 100 85 0 100

Surinam Grass 25 100 80 95 100 100 10 10 100 100 75 65 0 90

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 0 100

Wheat 35 60 65 60 85 70 30 40 100 100 60 100 80 85

Windgrass 30 20 50 70 70 80 40 40 70 45 60 60 45 70

Table B Compounds

4 g ai/ha 19 20 21 22 23 24 25 26 27 28 29 30 31 32

Postemergence

Barley 85 85 80 90 70 70 80 100 100 80 85 75 50 85

Bermudagrass 95 98 95 95 95 100 98 80 70 75 80 80 50 85

Blackgrass 70 80 70 60 80 85 65 70 65 60 60 60 50 65

Bromegrass, Downy 80 50 70 65 70 70 50 80 100 45 20 40 45 98

Canarygrass 100 100 100 80 90 100 100 85 70 80 70 60 55 100

Chickweed 100 100 100 100 98 100 100 85 98 98 90 75 55 95

Cocklebur 100 - 100 100 100 100 10 - - 100 100 100 80 65

Corn 80 100 95 75 75 95 75 85 70 25 100 25 20 100

Crabgrass, Lg 98 100 98 95 95 100 100 75 85 75 90 80 10 98

Cupgrass, Woolly 100 100 100 100 100 100 100 100 98 100 100 90 10 100

Deadnettle 50 70 60 50 80 60 60 50 65 50 50 50 60 50

Foxtail, Giant 100 100 100 100 100 100 100 75 100 100 100 100 45 100

Foxtail, Green 100 100 100 80 85 85 100 98 85 85 100 85 70 100

Galium 100 80 70 60 70 70 70 100 50 100 75 100 85 100

Goosegrass 90 98 95 85 90 100 95 45 70 70 75 70 65 75 Johnsongrass 85 100 98 85 90 98 100 - 100 80 70 100 75 98

Kochia 100 100 100 100 98 100 100 90 100 100 98 100 100 85

Lambsquarters 100 100 98 100 100 100 100 100 100 95 100 90 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 75 100

Nutsedge, Yellow 5 0 20 5 5 0 0 0 20 0 5 0 0 5

Oat, Wild 80 100 80 85 50 85 60 60 100 60 40 50 55 80

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 95 100 100 100 85 100 95 100 80 80 100

Ryegrass, Italian 50 60 50 40 30 50 50 45 50 40 55 25 40 60

Soybean 90 100 98 100 100 100 90 100 90 98 100 98 90 100

Surinam Grass 100 98 98 90 80 95 90 80 70 85 70 75 55 90

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 85 100 85 85 80 100 95 60 100 50 65 60 40 100

Windgrass 55 80 50 40 60 40 45 50 70 45 70 50 60 60

Table B Compounds

4 g ai/ha 33 35 36 38 39 40 41 42 43 44 45 46 47 49

Postemergence

Barley 45 - 85 85 80 100 100 80 85 - 45 80 70 60

Bermudagrass 40 90 80 98 60 80 95 65 70 65 45 95 45 75

Blackgrass 50 50 55 65 50 60 50 50 70 45 35 60 50 70

Bromegrass, Downy 60 45 50 60 60 60 40 50 70 - 50 60 70 35

Canarygrass 55 65 100 100 65 100 85 45 85 35 40 85 70 30

Chickweed 100 75 80 98 75 95 98 100 95 95 90 90 98 100

Cocklebur 80 - 100 100 100 100 - 100 - 100 100 100 100 100

Corn 60 75 85 100 95 95 100 55 100 45 0 100 65 55

Crabgrass, Lg 75 75 80 80 75 80 75 75 80 85 65 80 80 75

Cupgrass, Woolly 100 100 100 100 100 100 100 100 100 100 100 100 100 95

Deadnettle 45 50 60 40 50 40 55 55 40 60 70 75 80 85

Foxtail, Giant 95 100 80 100 98 100 100 75 100 98 100 98 100 75

Foxtail, Green 70 80 100 100 85 100 100 80 85 100 60 100 85 85

Galium 70 65 100 100 100 100 100 65 100 100 45 100 100 100

Goosegrass 60 40 60 20 60 75 55 60 60 55 65 75 80 5

Johnsongrass 80 85 100 100 - 100 100 85 80 90 100 85 70 60

Kochia 100 100 85 85 95 100 100 100 100 100 100 100 100 100

Lambsquarters 98 100 98 100 100 98 100 100 - 90 75 100 100 90

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 10 5 10 10 5 10 10 5 0 5 0 0

Oat, Wild 40 60 60 80 85 80 40 60 60 55 50 80 70 65 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 85 100 60 100 100 100 100 100

Ryegrass, Italian 40 40 50 50 45 50 40 40 45 30 10 35 40 20

Soybean 100 90 100 95 100 100 100 98 90 100 80 100 100 75

Surinam Grass 65 80 85 100 85 65 80 65 85 65 50 100 80 75

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 50 40 100 50 60 100 85 50 40 50 45 95 55 85

Windgrass 60 45 55 50 65 75 55 40 60 40 35 55 40 30

Table B Compounds

4 g ai/ha 50 51 52 53 55 56 62 64 65 66 67 70 77 80

Postemergence

Barley 85 75 80 20 80 80 10 40 55 60 50 60 100 50

Bermudagrass 90 85 30 85 98 100 85 45 0 90 70 75 65 70

Blackgrass 80 80 60 45 75 70 40 60 45 70 30 60 70 60

Bromegrass, Downy 85 85 70 70 65 65 40 60 50 85 70 80 98 50

Canarygrass 80 100 60 60 100 100 50 35 60 80 70 100 70 70

Chickweed 98 100 100 100 100 100 100 98 90 90 98 100 100 100

Cocklebur 100 100 100 100 100 - 75 100 100 100 - - 100 100

Corn 100 85 85 80 90 85 10 75 75 85 55 85 10 85

Crabgrass, Lg 90 80 75 75 100 95 70 75 75 75 70 95 75 75

Cupgrass, Woolly 100 100 100 98 100 100 90 100 100 100 100 100 90 100

Deadnettle 80 65 70 40 70 70 70 70 70 80 60 60 80 60

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 98 100 100 100

Foxtail, Green 80 100 85 85 100 100 80 85 85 80 70 80 98 100

Galium 100 100 100 100 65 80 70 85 100 100 80 100 70 100

Goosegrass 98 75 65 75 95 95 65 65 70 70 70 70 55 70

Johnsongrass 95 70 100 98 100 98 75 85 100 70 75 70 100 80

Kochia 100 100 100 100 98 100 100 100 100 70 80 95 100 85

Lambsquarters 100 100 100 100 100 98 100 85 100 100 80 98 100 80

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 10 0 - 0 0 0 0 0 0 0 0 0 0 0

Oat, Wild 85 80 75 70 60 75 65 80 55 85 80 100 80 70

Pigweed 100 100 100 100 100 100 100 100 - 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 95 100 100 100

Ryegrass, Italian 50 50 45 35 45 45 30 40 35 50 45 60 30 50

Soybean 100 85 100 100 95 90 80 100 100 100 85 100 90 85

Surinam Grass 100 100 80 70 100 75 70 80 85 100 85 100 100 60

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 80 100 75 65 85 70 30 45 40 50 100 98 100 70

Windgrass 45 65 60 60 70 50 30 50 55 65 40 70 45 50

Table B Compounds

4 g ai/ha 81 85 86 88 90 91 94 100 101 102 103 104 108 113

Postemergence

Barley 50 60 80 55 85 80 85 55 85 100 80 100 70 100

Bermudagrass 80 65 - 80 40 60 80 55 70 10 10 65 65 15

Blackgrass 35 65 100 55 60 80 75 40 75 50 - 85 45 50

Bromegrass, Downy 30 70 80 60 45 80 45 45 40 85 55 60 100 65

Canarygrass 60 70 80 60 80 85 80 20 35 85 50 60 55 65

Chickweed 98 85 90 100 95 100 100 10 95 100 80 100 65 100

Cocklebur - 100 100 100 100 100 100 15 100 100 - 100 95 100

Corn 65 60 85 80 45 65 90 10 10 95 40 98 100 20

Crabgrass, Lg 80 70 75 75 80 75 70 5 70 65 80 90 60 85

Cupgrass, Woolly 100 100 100 100 100 100 98 5 100 100 75 100 100 100

Deadnettle 80 60 60 80 60 65 45 50 80 - 80 80 - 60

Foxtail, Giant 100 100 100 100 100 100 100 10 100 100 98 100 100 100

Foxtail, Green 75 85 85 100 85 80 85 55 100 80 80 100 70 40

Galium 100 100 100 70 100 100 100 98 80 - 50 10 - 50

Goosegrass 75 75 60 70 70 65 70 45 10 10 10 70 30 30

Johnsongrass 70 65 65 75 45 65 75 0 70 100 - 100 100 80

Kochia 75 95 100 70 55 100 100 100 100 100 10 95 100 100

Lambsquarters 98 80 85 95 75 98 98 80 100 100 98 85 75 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 - 100

Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 10 0 35

Oat, Wild 50 80 80 80 80 70 70 45 75 85 50 80 80 85

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 90 95 90 25 100 70 70 100 40 75

Ryegrass, Italian 30 45 50 40 60 50 50 10 35 50 40 45 50 25

Soybean 80 80 85 85 80 90 95 70 85 60 25 65 70 80

Surinam Grass 70 100 80 80 95 70 75 30 100 100 65 75 65 55

Velvetleaf 100 100 100 75 100 100 100 100 100 100 70 100 100 100

Wheat 40 85 100 70 85 85 80 30 80 85 100 100 85 55

Windgrass 50 60 70 50 60 50 50 40 55 60 50 40 55 50

Table B Compounds

4 g ai/ha 119 120 122 123 125 126 127 128 130 137 140 141 142 143

Postemergence Barley 70 60 90 80 70 55 100 98 55 85 80 80 65 98

Bermudagrass 10 10 10 35 100 10 85 15 60 100 85 70 80 75

Blackgrass 90 40 50 60 60 50 100 65 60 50 65 50 60 60

Bromegrass, Downy 80 70 40 100 70 50 40 65 45 80 55 50 45 60

Canarygrass 65 35 40 45 70 50 85 40 35 85 55 70 80 100

Chickweed 65 10 10 10 100 65 100 100 100 98 98 100 95 90

Cocklebur 100 - 100 - 100 65 100 80 15 100 100 65 100 100

Corn 95 80 75 95 100 60 90 40 15 75 55 15 0 90

Crabgrass, Lg 65 80 55 70 100 55 85 85 65 95 75 60 80 85

Cupgrass, Woolly 100 90 98 85 100 100 98 100 20 100 98 100 100 100

Deadnettle 50 - - 85 55 98 80 70 60 50 50 60 50 50

Foxtail, Giant 85 100 75 75 100 100 100 98 80 100 100 75 98 90

Foxtail, Green 40 40 30 40 100 55 100 75 60 100 70 60 100 100

Galium 50 60 50 45 55 100 50 50 45 100 65 65 100 100

Goosegrass 10 45 10 60 100 45 75 10 65 95 70 50 65 70

Johnsongrass 100 70 100 100 80 90 100 98 70 - 75 98 70 85

Kochia 100 10 80 10 100 65 100 95 95 100 100 98 100 95

Lambsquarters 100 10 85 100 98 100 100 100 80 100 98 100 100 98

Morningglory 100 70 100 100 100 100 100 100 80 100 100 100 100 100

Nutsedge, Yellow 45 20 20 0 5 30 25 0 0 5 0 5 0 0

Oat, Wild 85 40 60 85 60 50 100 50 45 70 60 50 70 50

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 60 90 - 95 100 100 100 60 98 90 70 90 90

Ryegrass, Italian 60 40 30 35 30 40 40 35 30 40 40 30 50 50

Soybean 90 75 60 100 85 85 100 60 70 95 45 65 100 95

Surinam Grass 100 75 75 100 100 100 75 65 10 70 65 65 75 98

Velvetleaf 100 100 100 100 100 100 100 100 75 100 100 100 100 100

Wheat 100 60 85 100 85 100 100 85 45 80 60 60 65 70

Windgrass 70 20 50 35 45 50 50 45 40 70 50 45 60 60

Table B Compounds

4 g ai/ha 144 146 147 150 153 201 211 212 214 215 216 217 402

Postemergence

Barley 85 35 85 45 40 55 100 85 80 85 80 85 30

Bermudagrass 80 5 85 65 10 10 65 15 85 55 75 70 65

Blackgrass 80 40 65 30 35 30 45 55 60 40 60 50 20

Bromegrass, Downy 85 30 70 50 50 65 40 60 75 80 80 70 50

Canarygrass 100 50 100 50 40 25 30 30 85 85 98 80 20

Chickweed 100 10 98 100 95 45 100 80 100 85 100 100 100 Cocklebur 100 10 - 100 70 95 - - 100 10 100 100 -

Corn 85 10 100 55 50 65 65 35 98 80 80 85 55

Crabgrass, Lg 95 10 85 80 45 65 75 40 90 80 85 80 75

Cupgrass, Woolly 100 85 95 100 70 75 100 75 100 100 95 100 45

Deadnettle 65 50 50 - 98 98 50 80 50 60 45 50 -

Foxtail, Giant 100 5 100 98 70 60 100 70 100 100 100 100 55

Foxtail, Green 98 65 100 95 40 10 20 40 85 98 70 85 100

Galium 80 65 100 - 50 45 30 50 70 70 65 65 -

Goosegrass 65 10 75 75 10 10 85 10 85 40 75 70 65

Johnsongrass 100 100 100 98 70 60 100 50 95 100 95 90 65

Kochia 100 100 100 100 100 10 100 65 100 100 98 100 100

Lambsquarters 100 75 100 98 60 10 100 80 100 80 100 100 98

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 10 5 50 0 10 0 0 0 0 0 10

Oat, Wild 65 45 80 80 85 60 50 45 60 65 60 60 50

Pigweed 100 100 100 100 100 100 100 98 100 100 100 100 100

Ragweed 100 100 100 100 35 100 100 85 100 100 90 80 70

Ryegrass, Italian 50 30 50 30 40 50 30 25 45 35 40 40 45

Soybean 100 20 100 75 60 65 80 20 100 75 80 90 75

Surinam Grass 85 15 98 75 75 65 90 10 95 20 98 100 60

Velvetleaf 100 75 100 100 100 50 100 70 100 100 100 100 100

Wheat 100 60 100 80 50 85 80 80 60 100 60 40 35

Windgrass 40 10 75 65 60 40 30 35 40 30 50 50 50

Table B Compound Table B Compound

125 g ai/ha 19 62 g ai/ha 19

Preemergence Preemergence

Bermudagrass 100 Bermudagrass 100

Blackgrass 90 Blackgrass 50

Bromegrass, Downy 80 Bromegrass, Downy 60

Cocklebur 100 Cocklebur 100

Corn 90 Corn 75

Crabgrass, Lg 100 Crabgrass, Lg 100

Cupgrass, Woolly 100 Cupgrass, Woolly 100

Foxtail, Giant 100 Foxtail, Giant 75

Foxtail, Green 100 Foxtail, Green 100

Galium 100 Galium 100

Goosegrass 100 Goosegrass 85

Johnsongrass 100 Johnsongrass 98 Kochia 100 Kochia 98

Lambsquarters 100 Lambsquarters 100

Morningglory 100 Morningglory 100

Nightshade 100 Nightshade 100

Nutsedge, Yellow 70 Nutsedge, Yellow 65

Oat, Wild 45 Oat, Wild 40

Pigweed 100 Pigweed 100

Ragweed 100 Ragweed 100

Russian Thistle 100 Russian Thistle 80

Ryegrass, Italian 70 Ryegrass, Italian 55

Soybean 100 Soybean 100

Sunflower 100 Sunflower 100

Surinam Grass 100 Surinam Grass 100

Velvetleaf 100 Velvetleaf 100

Wheat 40 Wheat 40

Table B Compounds

31 g ai/ha 1 2 3 4 5 13 14 15 16 17 19 20 24 25

Preemergence

Bermudagrass 90 45 95 80 95 98 98 100 100 100 80 100 98 100

Blackgrass 5 30 30 30 50 90 55 80 100 70 50 80 70 85

Bromegrass, Downy 0 25 55 60 70 70 60 98 100 98 40 80 80 80

Cocklebur 0 0 50 45 50 80 98 - - 45 100 100 100 100

Corn 0 0 0 0 20 60 65 65 85 75 10 75 30 45

Crabgrass, Lg 80 98 95 100 100 100 100 100 70 100 95 100 100 100

Cupgrass, Woolly 80 100 80 70 100 100 100 100 100 100 100 100 100 100

Foxtail, Giant 55 80 95 90 60 80 75 98 65 70 65 100 95 95

Foxtail, Green 85 98 100 100 100 98 100 100 100 100 98 100 100 100

Galium 0 90 100 75 100 100 100 100 100 100 100 100 100 100

Goosegrass 100 100 80 85 80 95 85 60 90 98 85 98 95 90

Johnsongrass 100 100 80 65 85 85 75 80 98 85 70 100 98 90

Kochia 98 75 100 10 95 80 100 60 100 100 0 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 0 100 90 100 100 100 100 100 100 98 98 100 100 100

Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 0 15 60 20 45 40 60 55 20 45 35 55

Oat, Wild 0 5 5 10 0 30 40 - 80 40 30 40 45 10

Pigweed 100 100 100 100 100 100 100 100 100 100 98 100 100 100 Ragweed 60 90 100 90 100 100 100 100 100 100 100 100 100 100

Russian Thistle - - - - - 100 90 - - 98 50 100 100 100

Ryegrass, Italian 0 40 50 20 100 45 45 70 60 60 50 65 90 100

Soybean 0 0 50 50 80 98 100 100 100 100 90 100 95 95

Sunflower 0 75 85 60 90 100 85 100 100 100 80 100 100 100

Surinam Grass 60 95 100 60 80 95 100 100 100 100 98 100 100 100

Velvetleaf 80 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 10 0 0 0 0 10 35 35 40 25 20 30 30 40

Table B Compounds

31 g ai/ha 27 28 29 30 32 41 44 49 55 56 77 94 101 126

Preemergence

Bermudagrass 98 100 100 75 98 100 100 65 100 100 25 100 20 100

Blackgrass 98 40 50 10 30 30 20 5 60 70 25 45 30 85

Bromegrass, Downy 100 35 60 10 60 10 10 10 100 80 30 60 15 -

Cocklebur - 100 100 100 100 40 100 20 100 100 100 100 0 100

Corn 80 45 25 15 10 20 20 45 10 0 45 5 10 65

Crabgrass, Lg 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Cupgrass, Woolly 98 80 100 100 100 100 100 100 100 100 98 95 100 100

Foxtail, Giant 98 80 98 90 95 85 70 60 100 98 70 90 80 70

Foxtail, Green 100 98 100 98 100 80 95 80 100 100 85 100 100 98

Galium 100 100 100 90 100 100 100 100 100 100 95 100 100 100

Goosegrass 75 65 98 55 95 80 80 60 90 98 95 98 98 10

Johnsongrass 90 75 95 65 85 70 75 60 90 98 60 95 35 100

Kochia 100 0 100 100 100 100 100 100 98 100 98 45 100 98

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 100 0 60 0 100 100 75 75 85 20 40 98 20 100

Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 45 0 65 100 0 0 0 100 65 0 0 50 0 20

Oat, Wild 70 10 40 0 40 0 5 0 40 60 0 20 0 -

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 100 100 100 100 100 100 100 -

Russian Thistle - 100 100 75 95 80 50 100 100 100 100 100 100 -

Ryegrass, Italian 70 30 40 35 10 20 0 10 60 40 45 45 10 90

Soybean 100 40 98 20 100 55 95 60 100 20 98 85 95 100

Sunflower 100 60 100 45 100 85 100 100 100 100 100 100 65 100

Surinam Grass 100 80 100 100 95 85 70 100 100 100 98 100 65 65

Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 40 5 5 0 5 5 5 0 30 15 10 0 5 30 Table B Compounds

31 g ai/ha 142 143 147 214 216 217 402

Preemergence

Bermudagrass 100 100 100 75 65 98 45

Blackgrass 45 60 55 20 40 15 30

Bromegrass, Downy 45 65 30 15 5 60 5

Cocklebur 0 45 100 100 100 100 0

Corn 15 0 5 5 5 0 15

Crabgrass, Lg 100 100 100 100 100 100 100

Cupgrass, Woolly 100 95 100 100 100 95 75

Foxtail, Giant 85 85 95 98 70 85 100

Foxtail, Green 100 100 98 100 95 90 98

Galium 98 80 98 100 85 85 -

Goosegrass 100 70 90 95 95 98 65

Johnsongrass 75 75 85 90 85 70 100

Kochia 100 100 100 100 0 100 100

Lambsquarters 100 100 100 100 100 100 100

Morningglory 0 85 100 90 45 40 100

Nightshade 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 0 60 0 0 0

Oat, Wild 5 35 60 10 0 10 0

Pigweed 100 100 100 100 100 100 100

Ragweed 100 100 100 100 100 100 45

Russian Thistle 100 100 90 90 35 100 -

Ryegrass, Italian 60 50 30 5 20 30 50

Soybean 100 40 100 100 0 0 0

Sunflower 65 100 100 100 0 45 40

Surinam Grass 80 100 95 100 70 95 0

Velvetleaf 100 100 100 100 100 100 100

Wheat 0 10 0 0 0 5 0

Table B Compounds

16 g ai/ha 1 2 3 4 5 13 14 15 16 17 19 20 24 25

Preemergence

Bermudagrass 20 - 20 70 80 98 95 80 80 95 65 100 98 98

Blackgrass 0 30 15 20 45 35 50 - 90 70 30 60 60 65

Bromegrass, Downy 0 20 50 45 70 40 30 80 100 55 5 80 80 80

Cocklebur 0 0 0 20 30 0 25 - - 15 20 100 100 20

Corn 0 0 0 0 0 50 45 60 45 25 0 5 10 15 Crabgrass, Lg 80 95 90 75 80 100 80 85 25 100 55 85 100 98

Cupgrass, Woolly 70 95 80 70 40 95 98 100 100 100 98 98 65 100

Foxtail, Giant 40 75 70 55 25 65 45 60 45 65 55 75 85 70

Foxtail, Green 50 80 90 100 85 95 90 100 75 100 85 100 90 100

Galium 0 50 100 75 100 90 85 100 95 100 80 100 100 100

Goosegrass 100 60 80 55 60 45 80 20 70 90 40 90 65 75

Johnsongrass 55 100 75 65 65 65 65 75 80 70 0 100 95 80

Kochia 55 0 85 0 35 75 80 45 55 98 0 100 100 100

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 0 98 50 50 100 20 0 55 100 40 20 60 20 100

Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Yellow 0 0 0 0 55 0 0 0 0 0 0 0 0 25

Oat, Wild 0 0 0 0 0 30 30 55 50 40 30 40 45 10

Pigweed 100 100 100 100 100 100 100 100 100 100 98 100 100 100

Ragweed 45 80 100 70 95 100 100 100 100 100 98 100 100 100

Russian Thistle - - - - - 100 40 - - 98 50 100 100 100

Ryegrass, Italian 0 10 10 - 100 30 10 40 50 50 10 - 75 45

Soybean 0 0 - 0 70 20 15 90 90 80 65 100 0 25

Sunflower 0 65 50 45 75 100 65 100 100 45 45 100 65 100

Surinam Grass - 75 75 50 60 75 65 100 100 70 98 100 75 100

Velvetleaf 0 100 100 100 100 100 100 100 100 100 100 100 100 100

Wheat 0 0 0 0 0 0 0 30 25 25 5 0 30 25

Table B Compounds

16 g ai/ha 27 28 29 30 32 41 44 49 55 56 77 94 101 126

Preemergence

Bermudagrass 80 0 85 0 65 45 98 0 90 98 20 100 0 100

Blackgrass 35 40 20 0 5 10 0 5 50 55 5 45 5 10

Bromegrass, Downy 100 5 30 5 40 5 5 0 80 45 5 40 5 -

Cocklebur - 0 98 0 90 - 0 0 15 0 100 0 0 100

Corn 70 10 15 5 0 10 15 20 - 0 25 5 0 65

Crabgrass, Lg 95 65 100 100 98 90 100 80 100 98 70 90 100 70

Cupgrass, Woolly 65 0 100 65 100 85 100 80 98 100 85 50 98 20

Foxtail, Giant 35 40 75 55 65 65 55 55 85 65 40 55 65 15

Foxtail, Green 100 95 85 80 90 75 - 80 100 100 80 85 98 85

Galium 100 98 5 50 100 80 100 100 100 98 95 50 100 100

Goosegrass 5 40 95 40 60 45 60 20 90 80 35 75 20 0

Johnsongrass 65 45 85 45 80 55 55 55 85 90 55 80 20 100

Kochia 95 0 0 0 100 100 98 100 98 20 65 - 0 50 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 65 0 50 0 55 45 65 0 60 0 0 45 0 60

Nightshade 100 100 100 100 100 100 100 98 100 100 100 100 100 100

Nutsedge, Yellow 0 0 55 0 0 0 0 0 0 0 0 5 0 0

Oat, Wild 55 0 40 0 - 0 0 0 40 40 0 20 0 80

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 100 100 100 95 100 98 100 100 100 100 100 100 0 -

Russian Thistle - 60 50 75 90 15 20 70 100 30 100 30 100 -

Ryegrass, Italian 45 30 30 30 10 5 0 0 45 - 5 20 5 5

Soybean 100 0 45 0 98 20 20 0 45 0 80 45 75 100

Sunflower 45 0 85 0 98 20 85 65 80 40 85 45 60 100

Surinam Grass 70 20 70 90 65 70 65 100 98 80 85 95 60 45

Velvetleaf 100 90 100 100 100 80 100 98 100 85 100 100 100 100

Wheat 10 0 0 0 0 0 5 0 20 5 0 0 0 5

Table B Compounds

16 g ai/ha 142 143 147 214 216 217 402

Preemergence

Bermudagrass 100 100 45 45 45 55 10

Blackgrass 10 30 - 5 5 15 25

Bromegrass, Downy 45 40 30 5 0 5 5

Cocklebur - 0 100 100 0 100 0

Corn 0 0 5 0 0 0 0

Crabgrass, Lg 100 80 98 85 95 100 0

Cupgrass, Woolly 100 75 100 60 70 85 65

Foxtail, Giant 70 50 70 40 55 50 55

Foxtail, Green 100 85 95 90 85 90 45

Galium 50 40 90 50 85 85 0

Goosegrass 100 0 65 55 0 20 45

Johnsongrass 60 70 80 45 85 65 85

Kochia 80 0 100 0 0 65 20

Lambsquarters 100 100 100 100 100 100 100

Morningglory 0 25 45 20 0 0 0

Nightshade 100 100 100 100 100 100 80

Nutsedge, Yellow 0 0 0 15 0 0 0

Oat, Wild 5 5 20 0 0 5 0

Pigweed 100 100 100 100 100 100 100

Ragweed 100 100 100 100 98 100 0

Russian Thistle 85 30 0 40 - 70 - Ryegrass, Italian 50 10 30 5 5 30 0

Soybean 0 0 98 45 0 0 0

Sunflower 0 55 100 100 0 0 0

Surinam Grass 75 70 65 80 65 50 -

Velvetleaf 90 100 100 100 100 100 65

Wheat 0 5 0 0 0 0 0

Table B Compounds

8 g ai/ha 1 2 3 4 5 13 14 15 16 17 20 24 25 27

Preemergence

Bermudagrass 10 0 0 60 70 60 75 25 65 80 100 98 40 50

Blackgrass 0 20 10 10 20 30 40 - 40 10 60 50 45 35

Bromegrass, Downy 0 5 20 0 0 10 30 35 100 10 30 40 50 100

Cocklebur 0 0 0 0 0 0 - - - 0 35 25 0 -

Corn 0 0 0 0 0 0 0 25 40 15 5 0 10 55

Crabgrass, Lg 0 75 50 60 15 85 50 0 20 98 85 100 98 60

Cupgrass, Woolly 0 75 65 60 20 80 25 75 45 95 80 45 100 30

Foxtail, Giant 0 65 0 50 15 15 0 0 0 45 0 25 65 0

Foxtail, Green 50 80 20 80 70 65 90 85 55 95 85 90 90 70

Galium 0 50 50 75 80 30 20 100 95 100 98 100 80 100

Goosegrass 98 50 60 55 45 45 0 0 0 80 0 20 20 0

Johnsongrass 0 100 65 60 20 45 0 0 55 55 75 75 55 60

Kochia 0 0 0 0 - 0 65 0 45 85 100 98 20 45

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 0 75 0 35 70 20 0 50 10 20 0 15 55 25

Nightshade 98 90 100 95 60 98 98 100 100 100 100 98 100 100

Nutsedge, Yellow 0 0 0 0 25 0 0 0 0 0 0 0 0 0

Oat, Wild 0 0 0 0 0 0 0 55 45 30 40 - 10 50

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 0 40 70 0 80 100 100 100 100 100 100 100 100 100

Russian Thistle - - - - - 40 - - - 98 98 95 70 -

Ryegrass, Italian 0 - 0 0 100 30 10 35 35 30 50 35 45 -

Soybean 0 0 0 0 50 0 0 90 80 50 0 0 10 90

Sunflower 0 55 0 20 65 0 65 100 0 40 40 25 20 0

Surinam Grass - 20 70 25 55 70 25 65 60 45 90 70 75 0

Velvetleaf 0 25 75 55 98 100 65 95 100 100 100 65 65 100

Wheat 0 0 0 0 0 0 0 20 20 5 0 - 20 5 Table B Compounds

8 g ai/ha 28 29 30 32 41 44 49 55 56 77 94 101 126 142

Preemergence

Bermudagrass 0 0 0 45 0 85 0 0 15 10 100 0 25 100

Blackgrass 0 0 0 5 0 0 5 40 40 5 5 0 5 0

Bromegrass, Downy 5 0 0 25 0 0 0 30 5 0 5 0 - 0

Cocklebur - 0 0 0 0 - 0 0 0 0 - 0 0 0

Corn 5 10 0 0 5 15 0 0 0 20 0 0 15 0

Crabgrass, Lg 0 70 60 20 65 65 0 98 70 65 65 98 0 95

Cupgrass, Woolly 0 100 0 70 45 100 55 98 65 75 45 80 0 65

Foxtail, Giant 15 60 15 40 0 40 55 65 0 40 40 0 0 35

Foxtail, Green 65 50 80 85 20 60 40 90 80 70 80 70 75 60

Galium 20 0 20 100 80 0 95 98 0 0 40 98 100 20

Goosegrass 0 20 20 35 0 55 0 0 0 10 5 0 0 15

Johnsongrass 5 60 0 20 5 0 10 65 45 45 5 10 100 45

Kochia 0 0 0 45 0 80 0 95 0 20 0 0 0 0

Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Morningglory 0 0 0 55 0 20 0 0 0 0 0 0 40 0

Nightshade 98 100 95 100 100 100 90 100 85 98 100 100 100 100

Nutsedge, Yellow 0 15 0 0 0 0 0 0 0 0 0 0 0 0

Oat, Wild 0 5 0 40 0 0 0 30 30 0 0 0 0 0

Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Ragweed 98 98 85 100 55 100 100 100 100 100 100 0 - 20

Russian Thistle 0 0 20 20 10 0 - 70 0 0 30 20 - 10

Ryegrass, Italian 10 5 0 5 0 0 0 35 0 0 20 5 5 20

Soybean 0 0 0 0 0 0 0 0 0 50 0 70 95 0

Sunflower 0 0 0 60 0 65 0 65 20 15 0 45 65 0

Surinam Grass 0 45 10 45 60 65 60 98 80 40 65 0 15 60

Velvetleaf 20 100 95 75 65 70 50 65 70 80 90 55 100 0

Wheat 0 0 0 0 0 0 0 10 5 0 0 0 0 0

Table B Compounds

8 g ai/ha 143 147 214 216 217 402

Preemergence

Bermudagrass 0 0 0 0 0 0

Blackgrass 5 50 0 0 5 20

Bromegrass, Downy 0 30 0 0 0 0

Cocklebur - 70 0 0 0 0

Corn 0 5 0 0 0 0 Crabgrass, Lg 65 20 60 85 98 0

Cupgrass, Woolly 0 95 40 25 0 0

Foxtail, Giant 35 40 35 50 45 45

Foxtail, Green 80 40 90 85 85 40

Galium 40 80 50 60 35 0

Goosegrass 0 10 45 0 0 0

Johnsongrass 50 40 45 45 60 0

Kochia 0 0 0 0 20 0

Lambsquarters 100 100 100 100 100 98

Morningglory 0 45 0 0 0 0

Nightshade 100 100 98 20 100 70

Nutsedge, Yellow 0 0 0 0 0 0

Oat, Wild 0 0 0 0 0 0

Pigweed 100 100 100 98 100 100

Ragweed 100 100 80 60 100 0

Russian Thistle - 0 0 - 0 -

Ryegrass, Italian 0 10 5 5 0 0

Soybean 0 40 20 0 0 -

Sunflower 45 60 20 0 0 0

Surinam Grass 45 50 75 55 45 -

Velvetleaf 75 100 60 40 20 0

Wheat 0 0 0 0 0 0

Table B Compounds

4 g ai/ha 1 2 3 4 5 13 14 15 16 17 20 24 25 27

Preemergence

Bermudagrass 0 0 0 35 65 0 0 0 60 45 20 20 0 40

Blackgrass 0 0 0 0 5 0 0 20 0 10 30 50 45 30

Bromegrass, Downy 0 0 0 0 0 0 10 30 85 10 30 0 30 100

Cocklebur 0 0 0 0 0 0 - - - 0 - 0 - -

Corn 0 0 0 0 0 0 0 0 10 0 0 0 0 0

Crabgrass, Lg 0 65 40 50 0 0 40 0 20 80 55 75 55 0

Cupgrass, Woolly 0 - - 35 - 45 0 0 20 65 0 0 35 0

Foxtail, Giant 0 65 0 40 0 0 0 0 0 20 0 15 45 0

Foxtail, Green 40 80 - 50 70 55 40 55 30 70 85 60 70 5

Galium 0 0 0 30 10 30 0 0 0 10 80 20 80 70

Goosegrass 20 0 - 40 20 0 0 0 0 0 0 15 0 0

Johnsongrass 0 95 65 60 - 45 0 0 0 20 65 20 45 50

Kochia 0 0 0 0 0 0 40 0 40 0 0 0 0 0 Lambsquarters 85 98 100 95 40 100 100 100 100 100 100 100 100 100

Morningglory 0 0 0 0 40 20 0 0 0 0 - 0 0 0

Nightshade 0 45 100 80 - 65 75 45 60 95 100 98 98 65

Nutsedge, Yellow 0 0 0 0 20 0 0 0 0 0 0 0 0 0

Oat, Wild 0 0 0 0 0 - 0 50 45 0 30 40 10 50

Pigweed 100 100 50 95 70 100 100 100 100 100 100 100 100 100

Ragweed 0 0 10 0 60 85 0 100 90 100 100 100 100 100

Russian Thistle - - - - - 20 0 - - 0 0 0 0 -

Ryegrass, Italian 0 - 0 0 100 0 0 35 0 30 5 0 45 45

Soybean 0 0 0 0 30 0 0 85 75 0 0 0 0 85

Sunflower 0 55 0 0 60 0 0 0 0 0 - 0 0 0

Surinam Grass 0 0 50 0 0 45 0 10 40 20 65 70 65 0

Velvetleaf 0 0 60 30 65 50 0 75 80 0 - 40 45 98

Wheat 0 0 0 0 0 0 0 0 20 5 0 0 20 0

Table B Compounds

4 g ai/ha 28 29 30 32 41 44 49 55 56 77 94 101 126 142

Preemergence

Bermudagrass 0 0 0 0 0 0 0 0 0 0 0 0 0 65

Blackgrass 0 0 0 0 0 0 0 40 30 0 0 0 5 0

Bromegrass, Downy 0 0 0 0 0 0 0 0 5 0 0 0 - 0

Cocklebur 0 0 - 0 0 0 0 - 0 0 0 - - 0

Corn 0 5 0 0 0 5 0 0 0 20 0 0 0 0

Crabgrass, Lg 0 0 0 0 55 10 0 65 0 55 0 45 0 60

Cupgrass, Woolly 0 85 0 60 0 100 0 0 15 60 0 45 0 55

Foxtail, Giant 0 55 0 20 0 20 10 0 0 10 35 0 0 20

Foxtail, Green 60 0 20 70 20 60 40 60 75 20 0 5 5 5

Galium 0 0 20 55 80 0 95 0 0 0 10 90 0 0

Goosegrass 0 0 15 0 0 40 0 0 0 0 0 0 0 0

Johnsongrass 0 50 0 0 0 0 0 45 0 10 0 0 100 10

Kochia 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Lambsquarters 100 100 100 100 100 100 98 100 100 100 100 100 100 100

Morningglory 0 0 0 45 0 0 0 0 0 0 0 0 0 0

Nightshade 0 100 20 100 100 98 75 100 0 85 95 98 100 100

Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Oat, Wild 0 0 0 0 0 0 0 30 30 0 0 0 0 0

Pigweed 100 100 100 85 85 75 100 100 90 100 95 100 100 100

Ragweed 0 98 55 45 40 95 100 100 100 95 95 0 - 0

Russian Thistle 0 0 0 0 0 0 0 30 0 - 0 0 - 0 Ryegrass, Italian 5 0 0 5 0 0 0 0 0 0 0 0 - 10

Soybean - 0 0 0 0 0 0 0 0 45 0 0 45 0

Sunflower 0 0 0 20 0 0 0 0 0 0 0 0 - 0

Surinam Grass 0 40 0 0 0 20 45 45 40 25 0 0 0 10

Velvetleaf 0 75 65 40 0 20 20 60 0 75 55 45 20 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table B Compounds

4 g ai/ha 143 147 214 216 217 402

Preemergence

Bermudagrass 0 0 0 0 0 0

Blackgrass 0 0 0 0 0 0

Bromegrass, Downy 0 0 0 0 0 0

Cocklebur 0 0 - 0 0 0

Corn 0 0 0 0 0 0

Crabgrass, Lg 45 0 0 0 65 0

Cupgrass, Woolly 0 60 0 20 0 0

Foxtail, Giant 25 0 0 20 0 0

Foxtail, Green 80 30 35 60 60 0

Galium 0 0 0 0 30 0

Goosegrass 0 0 0 0 0 0

Johnsongrass 45 0 0 25 40 0

Kochia 0 0 0 0 0 0

Lambsquarters 100 100 100 98 100 0

Morningglory 0 40 0 0 0 0

Nightshade 95 100 0 20 98 65

Nutsedge, Yellow 0 0 0 0 0 0

Oat, Wild 0 0 0 0 0 0

Pigweed 100 65 20 45 100 100

Ragweed 100 95 70 0 80 0

Russian Thistle 0 0 0 10 0 -

Ryegrass, Italian 0 0 0 0 0 0

Soybean 0 40 0 0 0 0

Sunflower 0 40 0 0 0 0

Surinam Grass 0 5 50 10 0 0

Velvetleaf 65 40 0 35 0 0

Wheat 0 0 0 0 0 0 TEST C

Seeds of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (crabgrass, lg; Digitaria sanguinalis), naked crabgrass (crabgrass, nk; Digitaria nuda), green foxtail (foxtail, green; Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), morningglory (Ipomoea lacunosa), purple nutsedge (nutsedge, purple; Cyperus rotundus), ragweed (Ambrosia elatior), black mustard (Brassica nigra), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloa crus-galli), sandbur (Cenchrus echinatus), sowthistle (Sonchus oleraceous), prickly sida (Sida spinosa), Italian ryegrass (ryegrass, It; Lolium multiflorum), purslane (Portulaca oleracea), signalgrass (Brachiaria platyphylla), groundsel (Senecio vulgaris), chickweed (Stellaria media), dayflower (dayflower, VA; Commelina virginica), bluegrass (Poa annua), itchgrass (Rottboellia cochinchinensis), quackgrass (Elytrigia repens), field bindweed (Convolvulus arvensis), spanishneedles (Bidens bipinnata), mallow (Malva sylvestris) and Russian thistle (Salsola kali) were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants from these weed species were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Table C Compound Table C Compound

250 g ai/ha 25 125 g ai/ha 25

Postemergence Postemergence

Barnyardgrass 100 Barnyardgrass 100

Bermudagrass 100 Bermudagrass 100

Black Mustard 100 Black Mustard 100

Bluegrass 50 Bluegrass 50

Chickweed 100 Chickweed 100

Crabgrass, Lg 100 Crabgrass, Lg 100

Crabgrass, Nk 100 Crabgrass, Nk 100

Dallisgrass 100 Dallisgrass 100

Dayflower, VA 100 Dayflower, VA 100

Field Bindweed 100 Field Bindweed 100

Foxtail, Green 100 Foxtail, Green 100

Goosegrass 95 Goosegrass 95 Groundsel 100 Groundsel 100

Guineagrass 100 Guineagrass 100

Itchgrass 100 Itchgrass 100

Johnsongrass 100 Johnsongrass 100

Kochia 100 Kochia 100

Mallow 100 Mallow 100

Morningglory 100 Morningglory 100

Nutsedge, Purple 60 Nutsedge, Purple 40

Prickly Sida 100 Prickly Sida 100

Purslane 100 Purslane 100

Quackgrass 100 Quackgrass 98

Ragweed 100 Ragweed 100

Russian Thistle 100 Russian Thistle 100

Ryegrass, It 75 Ryegrass, It 35

Sandbur 100 Sandbur 100

Signalgrass 98 Signalgrass 98

Spanishneedles 100 Spanishneedles 100

Surinam Grass 100 Surinam Grass 100

Table C Compounds Table C Compounds

62 g ai/ha 2 25 62 g ai/ha 2 25

Postemergence Postemergence

Barnyardgrass 100 100 Johnsongrass 100 100

Bermudagrass 100 100 Kochia - 100

Black Mustard 100 100 Mallow - 100

Bluegrass 80 35 Morningglory 100 100

Chickweed - 100 Nutsedge, Purple 60 25

Crabgrass, Lg 100 100 Prickly Sida - 100

Crabgrass, Nk 100 100 Purslane 100 100

Dallisgrass 100 95 Quackgrass 100 98

Dayflower, VA 100 100 Ragweed - 100

Field Bindweed - 100 Russian Thistle - 100

Foxtail, Green 100 100 Ryegrass, It 98 20

Goosegrass 98 80 Sandbur 100 100

Groundsel - 100 Signalgrass 100 75

Guineagrass 100 100 Spanishneedles - 100

Itchgrass 100 100 Surinam Grass 100 100 Table C Compounds

31 g ai/ha 2 6 13 14 19 20 25 27 55 113 119 120 122 125

Postemergence

Barnyardgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Bermudagrass 95 75 75 40 95 98 95 98 95 70 75 40 60 35

Black Mustard 100 90 90 30 60 100 95 90 80 70 100 75 100 95

Bluegrass 75 30 15 5 20 65 35 35 35 60 10 10 25 5

Chickweed - 100 100 100 100 100 100 100 100 100 100 100 100 -

Crabgrass, Lg 98 98 100 100 98 100 100 100 100 100 70 95 75 95

Crabgrass, Nk 100 90 100 100 100 100 100 100 100 100 100 100 100 98

Dallisgrass 100 80 80 65 100 80 85 100 85 100 100 0 85 65

Dayflower, VA 100 100 100 - 100 100 100 100 100 - 100 100 100 100

Field Bindweed - 100 100 100 100 100 100 100 100 100 100 100 100 98

Foxtail, Green 100 95 100 100 100 100 100 100 100 95 100 100 100 100

Goosegrass 98 50 35 25 90 100 80 85 85 40 20 40 35 20

Groundsel - 95 - - 100 100 100 100 100 - - 100 100 100

Guineagrass 100 98 100 90 100 100 100 100 100 100 100 100 100 100

Itchgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Kochia - 100 - - 100 100 100 100 100 - - 100 - 100

Mallow - 100 100 100 100 100 100 100 100 100 100 95 100 100

Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Nutsedge, Purple 60 35 - - 10 20 10 20 10 - - 25 10 20

Prickly Sida - 100 100 100 100 100 100 100 100 100 100 100 100 100

Purslane 100 100 100 100 100 100 100 100 100 100 100 100 100 100

Quackgrass 100 98 98 100 98 98 98 100 98 98 95 95 50 95

Ragweed - 98 100 100 100 100 100 100 100 100 100 100 100 100

Russian Thistle - 100 100 100 100 100 100 100 100 100 100 100 100 100

Ryegrass, It 70 65 60 - 25 15 5 20 10 65 95 35 75 25

Sandbur 100 35 100 50 100 100 100 100 100 75 100 100 100 100

Signalgrass 100 75 80 70 70 98 65 60 75 35 25 40 30 65

Sowthistle - 100 100 100 - - - - - 100 100 100 100 100

Spanishneedles - 98 100 100 100 100 100 100 100 100 100 100 100 100

Surinam Grass 100 40 100 50 100 100 100 85 95 85 98 100 90 100

Table C Compounds Table C Compounds

31 g ai/ha 126 127 149 150 31 g ai/ha 126 127 149

Postemergence Postemergence

Barnyardgrass 100 100 100 95 Kochia - 100 98 Bermudagrass 70 - 35 70 Mallow 98 100 60 100

Black Mustard 100 100 75 95 Morningglory 100 100 100 100

Bluegrass 10 20 5 70 Nutsedge, Purple 25 20 35 40

Chickweed 100 100 100 100 Prickly Sida 100 100 100 100

Crabgrass, Lg 100 98 60 80 Purslane 100 100 100 100

Crabgrass, Nk - 100 95 - Quackgrass 95 95 40 60

Dallisgrass 95 100 20 50 Ragweed - 100 75 100

Dayflower, VA 100 100 50 100 Russian Thistle 100 100 - 100

Field Bindweed 100 100 100 100 Ryegrass, It 70 30 25 65

Foxtail, Green 100 100 60 100 Sandbur 100 100 98 35

Goosegrass 50 75 35 40 Signalgrass 95 75 40 50

Groundsel 100 100 85 100 Sowthistle 100 100 100 100

Guineagrass 100 100 - 100 Spanishneedles 100 100 40 95

Itchgrass 100 100 100 100 Surinam Grass 100 100 95 100

Johnsongrass 100 100 100 98

Table C Compounds

16 g ai/ha 2 3 4 5 6 13 14 19 20 27 55 113 119 120

Postemergence

Barnyardgrass 100 100 100 100 100 100 80 100 100 100 100 100 80 100

Bermudagrass 90 50 95 85 75 75 40 95 95 95 90 70 60 35

Black Mustard 100 50 70 75 95 75 30 50 80 80 65 35 65 65

Bluegrass 65 20 20 40 20 10 5 20 40 30 30 10 5 10

Chickweed - 100 100 100 100 100 100 100 100 100 100 100 100 100

Crabgrass, Lg 98 95 90 98 90 90 100 95 100 100 98 85 65 95

Crabgrass, Nk 100 - - 100 90 100 95 98 98 100 98 95 65 100

Dallisgrass 98 70 70 95 - 80 35 95 75 100 - 65 75 0

Dayflower, VA 100 100 90 100 100 100 100 90 100 100 100 100 100 100

Field Bindweed - 100 100 100 100 100 100 100 100 100 100 95 100 100

Foxtail, Green 100 95 100 100 70 100 100 100 100 95 100 65 95 95

Goosegrass 95 75 80 75 40 20 25 85 65 85 75 10 20 10

Groundsel - 100 98 100 95 - - 100 100 98 100 - - 100

Guineagrass 100 98 100 100 98 100 75 100 100 100 100 95 100 40

Itchgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 98

Johnsongrass 100 100 100 100 100 95 98 100 100 100 100 - 75 95

Kochia - 100 100 100 85 - - 100 100 100 100 - - 100

Mallow - 100 100 100 100 100 100 100 100 100 100 98 100 85

Morningglory 100 100 100 100 100 100 - 100 100 - 100 100 100 100 Nutsedge, Purple 20 35 35 50 30 - - 10 20 20 5 - - 10

Prickly Sida - - 100 100 100 100 100 100 100 100 100 100 100 100

Purslane 100 100 100 100 100 100 100 100 100 100 100 95 100 98

Quackgrass 100 90 75 80 90 95 95 - 95 80 50 95 80 30

Ragweed - 100 100 100 90 100 100 100 100 100 100 100 100 100

Russian Thistle - - - - 100 95 85 100 100 100 100 100 100 100

Ryegrass, It 60 - 40 50 40 60 70 5 15 5 5 60 60 35

Sandbur 100 60 100 100 35 75 15 100 100 100 100 50 75 100

Signalgrass 95 50 50 70 70 10 35 40 70 60 50 10 20 35

Sowthistle - 100 100 100 100 100 100 - - - - 100 100 100

Spanishneedles - 100 100 100 75 100 100 100 100 100 100 100 100 100

Surinam Grass 100 - 100 100 - 100 30 100 100 85 75 65 85 90

Table C Compounds

16 g ai/ha 122 125 126 127 149 150

Postemergence

Barnyardgrass 75 100 100 100 100 90

Bermudagrass 50 35 50 95 30 60

Black Mustard 100 75 50 95 35 75

Bluegrass 20 5 5 5 5 60

Chickweed 100 100 100 100 70 100

Crabgrass, Lg 75 75 75 95 50 75

Crabgrass, Nk 95 90 98 95 80 -

Dallisgrass 75 5 0 100 5 50

Dayflower, VA 100 95 100 100 30 100

Field Bindweed 100 95 100 100 75 98

Foxtail, Green 90 100 100 100 35 98

Goosegrass 25 15 15 65 25 40

Groundsel 100 - 100 100 85 100

Guineagrass 95 100 95 100 100 98

Itchgrass 100 100 100 100 90 100

Johnsongrass 75 75 98 100 98 95

Kochia 100 100 100 100 70 98

Mallow 75 80 75 95 60 100

Morningglory 100 100 100 100 75 98

Nutsedge, Purple 10 10 25 10 25 35

Prickly Sida 100 100 100 100 70 100

Purslane 100 100 75 100 100 100

Quackgrass 25 85 95 90 25 35 Ragweed 100 100 100 100 60 95

Russian Thistle 100 100 100 100 - 100

Ryegrass, It 65 10 35 30 10 65

Sandbur 98 20 100 100 35 25

Signalgrass 30 - 30 60 35 50

Sowthistle 100 100 100 100 80 100

Spanishneedles 100 100 100 100 35 95

Surinam Grass 35 85 100 100 10 75

Table C Compounds

8 g ai/ha 2 3 4 5 6 13 14 19 20 27 55 113 119 120

Postemergence

Barnyardgrass 100 100 100 100 100 100 80 100 100 100 100 85 40 100

Bermudagrass 80 35 70 75 70 75 40 75 - 95 75 50 60 25

Black Mustard 100 30 65 70 65 65 30 50 65 75 60 20 50 10

Bluegrass 60 15 10 35 10 10 5 20 40 30 25 5 0 5

Chickweed - 100 100 100 100 100 100 100 100 100 100 100 98 100

Crabgrass, Lg 98 80 85 75 75 70 60 95 80 100 70 35 40 85

Crabgrass, Nk 90 - 100 100 75 85 95 85 95 100 75 - 50 100

Dallisgrass 95 5 50 90 70 35 35 70 75 70 65 65 75 0

Dayflower, VA 98 100 90 100 100 100 100 70 100 75 70 100 100 100

Field Bindweed - 100 100 100 98 100 95 100 100 100 100 95 100 95

Foxtail, Green 100 95 75 75 70 65 98 100 95 95 100 25 70 95

Goosegrass 70 65 65 75 40 5 20 30 35 25 - 10 5 10

Groundsel - 95 98 98 - - - 100 95 90 95 100 100 5

Guineagrass 100 70 100 100 98 100 - 100 100 100 98 95 75 40

Itchgrass 100 100 100 100 100 100 100 100 100 100 98 100 80 98

Johnsongrass 100 100 100 100 100 95 85 100 100 100 100 100 75 95

Kochia - 100 100 98 - - - 100 100 100 100 - - 80

Mallow - 100 100 100 65 85 95 100 100 100 100 95 65 40

Morningglory 100 100 100 100 100 90 85 100 100 - 100 100 100 100

Nutsedge, Purple 20 30 35 50 20 - - 5 10 15 5 - - 10

Prickly Sida - 100 100 100 100 100 100 100 100 100 100 100 80 100

Purslane 100 100 100 100 95 95 98 100 100 100 98 65 100 98

Quackgrass 95 80 70 65 60 70 70 95 75 75 25 80 65 25

Ragweed - 100 100 100 85 100 100 100 100 100 100 100 100 100

Russian Thistle - - - - - 95 85 100 100 100 100 75 100 5

Ryegrass, It 60 40 40 40 40 30 25 5 5 5 5 40 10 35

Sandbur 100 60 100 100 35 50 15 100 100 100 100 15 50 30 Signalgrass 90 40 40 70 40 5 40 30 50 30 5 10 35 Sowthistle 100 100 100 100 100 - 100 100 80 Spanishneedles 100 100 100 75 100 100 100 100 100 100 100 100

Surinam Grass 100 100 100 100 - 75 70 50 35 65 20 50 80

Table C Compounds

8 g ai/ha 122 125 126 127 149 150

Postemergence

Barnyardgrass 70 100 100 100 100 75

Bermudagrass 35 5 50 10 15 40

Black Mustard 50 60 30 95 35 65

Bluegrass 5 5 5 5 5 15

Chickweed 98 40 100 60 10 100

Crabgrass, Lg 35 50 50 95 35 65

Crabgrass, Nk 50 15 50 85 15 -

Dallisgrass 65 5 0 35 5 35

Dayflower, VA 100 80 90 100 30 100

Field Bindweed 100 95 100 100 75 75

Foxtail, Green 75 98 75 100 30 70

Goosegrass 5 5 5 15 10 35

Groundsel 100 70 100 100 60 95

Guineagrass 65 98 65 100 30 90

Itchgrass 50 95 95 98 65 95

Johnsongrass 75 35 98 90 90 95

Kochia 95 98 70 100 70 95

Mallow 60 65 75 95 35 100

Morningglory 100 98 100 100 75 95

Nutsedge, Purple 0 5 10 10 5 15

Prickly Sida 100 40 100 100 50 100

Purslane 100 100 75 100 35 100

Quackgrass 20 70 15 80 25 35

Ragweed 100 98 100 95 40 80

Russian Thistle 100 100 90 100 70 100

Ryegrass, It 50 10 10 20 5 65

Sandbur 20 - 100 100 35 25

Signalgrass 20 35 30 35 30 40

Sowthistle 100 95 100 100 60 100

Spanishneedles 100 100 100 100 20 75

Surinam Grass 10 50 100 75 - 60 Table C Compounds

4 g ai/ha 3 4 5 6 13 14 19 20 27 55 113 119 120 122

Postemergence

Barnyardgrass 100 98 98 98 100 25 100 100 100 98 85 40 95 35

Bermudagrass 35 65 75 70 70 40 75 80 95 65 35 20 20 5

Black Mustard 20 50 60 65 0 25 20 - 75 10 0 50 - 5

Bluegrass 15 10 20 10 5 5 5 20 5 5 5 0 5 5

Chickweed 100 - 100 85 100 100 90 100 100 100 100 90 75 85

Crabgrass, Lg 70 75 60 70 35 60 70 75 50 35 25 25 75 25

Crabgrass, Nk - - 100 75 80 90 70 95 100 50 - - 95 50

Dallisgrass 5 30 35 35 - 35 70 50 50 10 65 75 0 0

Dayflower, VA 90 75 100 50 100 100 50 100 20 50 100 100 35 50

Field Bindweed 100 100 100 80 95 90 100 100 100 100 90 95 95 98

Foxtail, Green 95 75 70 40 65 75 85 80 70 70 25 60 60 60

Goosegrass 65 50 65 35 5 15 10 25 10 15 5 5 5 5

Groundsel - 80 80 70 - - 100 90 80 95 100 100 5 100

Guineagrass 35 95 95 95 95 35 100 100 100 95 35 75 - 10

Itchgrass 100 100 100 100 100 100 95 100 75 90 95 70 80 50

Johnsongrass 98 98 100 100 70 80 95 90 100 30 70 70 95 75

Kochia 100 98 98 75 - - 100 100 100 100 - - 70 95

Mallow 100 100 100 65 75 65 100 100 95 70 95 60 40 60

Morningglory 95 100 100 90 90 - 100 100 100 98 75 100 100 100

Nutsedge, Purple 25 25 50 10 - - 5 10 5 5 - - 0 0

Prickly Sida 100 100 100 100 70 98 100 100 100 100 70 15 20 35

Purslane 100 100 100 95 80 10 100 100 85 98 0 50 80 100

Quackgrass 75 50 65 40 30 40 65 20 40 15 40 25 20 20

Ragweed 100 100 100 70 100 100 100 100 100 100 100 100 100 100

Russian Thistle - - - 100 85 85 100 100 100 100 70 98 5 100

Ryegrass, It 40 30 35 25 5 25 5 5 5 5 25 10 35 25

Sandbur 60 100 100 25 50 10 95 70 85 40 5 35 - 20

Signalgrass 35 30 50 40 5 15 40 30 35 - 5 5 35 0

Sowthistle 100 95 100 95 100 100 - - - - 85 100 65 100

Spanishneedles 100 100 95 70 98 - 100 100 100 100 100 100 60 100

Surinam Grass - - 98 - 65 15 25 20 35 25 10 50 25 5

Table C Compounds Table C Compounds

4 g ai/ha 125 126 127 149 150 4 g ai/ha 125 126 127 149 150

Postemergence Postemergence

Barnyardgrass 100 100 100 95 75 Kochia 95 - 100 60 95 Bermudagrass 5 50 5 15 20 Mallow 65 0 95 15 100

Black Mustard 50 20 65 35 65 Morningglory 98 100 100 35 70

Bluegrass 0 5 5 5 10 Nutsedge, Purple 5 5 5 0 10

Chickweed 40 98 - - 100 Prickly Sida 30 40 80 20 75

Crabgrass, Lg 50 35 80 20 60 Purslane 90 60 100 0 50

Crabgrass, Nk 5 35 70 - - Quackgrass 10 15 75 0 20

Dallisgrass 5 0 35 0 35 Ragweed 80 100 95 15 80

Dayflower, VA 5 - 90 5 50 Russian Thistle 95 90 100 50 95

Field Bindweed 75 100 98 75 70 Ryegrass, It 5 5 20 5 35

Foxtail, Green 98 75 100 20 50 Sandbur 5 50 70 5 25

Goosegrass 5 5 5 0 25 Signalgrass 5 10 35 30 35

Groundsel 60 75 70 35 95 Sowthistle 70 100 95 50 98

Guineagrass 35 65 100 0 70 Spanishneedles 100 65 100 5 60

Itchgrass 75 70 75 10 60 Surinam Grass 35 10 75 - 50

Johnsongrass 25 65 80 30 50

Table C Compounds Table C Compounds

2 g ai/ha 3 4 5 62 g ai/ha 2 6 15 27

Postemergence Preemergence

Barnyardgrass 20 98 98 Barnyardgrass 98 50 70 80

Bermudagrass 0 50 60 Bermudagrass 95 90 100 70

Black Mustard 5 30 60 Black Mustard 100 100 30 80

Bluegrass 10 10 5 Bluegrass 35 70 25 35

Chickweed 100 100 100 Chickweed - - 98 98

Crabgrass, Lg 50 60 60 Crabgrass, Lg 100 100 100 100

Crabgrass, Nk 100 - - Crabgrass, Nk - - 100 100

Dallisgrass 5 15 5 Dallisgrass 98 100 98 98

Dayflower, VA 90 15 30 Dayflower, VA 98 - 100 100

Field Bindweed 100 75 100 Field Bindweed - 100 100 100

Foxtail, Green 40 40 35 Foxtail, Green 100 80 95 100

Goosegrass 40 35 40 Goosegrass 98 50 85 90

Groundsel 80 80 80 Groundsel - - 100 100

Guineagrass 5 95 95 Guineagrass - 100 100 100

Itchgrass 90 100 95 Itchgrass 100 65 75 75

Johnsongrass 20 95 75 Johnsongrass 98 100 98 98

Kochia 95 60 98 Kochia - 100 100 100

Mallow 100 90 75 Mallow - 100 100 100

Morningglory 60 100 100 Morningglory 100 100 100 100 Nutsedge, Purple 20 25 35 Nutsedge, Purple 50 50 25 35

Prickly Sida 90 100 100 Prickly Sida - 100 100 100

Purslane 100 95 100 Purslane 100 100 100 100

Quackgrass 50 35 25 Quackgrass 35 60 40 65

Ragweed 100 85 100 Ragweed - 100 100 100

Ryegrass, It 10 20 35 Russian Thistle - 100 25 100

Sandbur 25 40 95 Ryegrass, It 40 60 40 35

Signalgrass 20 30 40 Sandbur 100 80 100 100

Sowthistle 85 95 98 Signalgrass 100 100 100 100

Spanishneedles 100 50 95 Sowthistle - 100 100 100

Surinam Grass 5 - 98 Spanishneedles - 100 100 100

Surinam Grass 100 100 100 98

Table C Compounds

31 g ai/ha 2 6 14 15 27 149 150

Preemergence

Barnyardgrass 70 40 90 35 40 15 20

Bermudagrass 90 60 60 60 70 0 35

Black Mustard 50 100 98 0 50 0 95

Bluegrass 30 40 65 20 0 0 0

Chickweed - - - 98 98 - -

Crabgrass, Lg 100 100 95 100 100 50 40

Crabgrass, Nk - - 100 100 100 65 95

Dallisgrass 80 100 95 95 80 0 35

Dayflower, VA 98 - 100 70 95 0 100

Field Bindweed - 100 100 100 100 80 95

Foxtail, Green 75 25 60 65 95 0 60

Goosegrass 35 25 35 70 0 0 40

Groundsel - - - 100 100 - -

Guineagrass - 100 100 100 95 75 100

Itchgrass 90 40 60 35 35 0 20

Johnsongrass 75 98 95 95 98 20 50

Kochia - 100 100 98 35 0 100

Mallow - 100 100 98 100 98 98

Morningglory 85 90 100 100 75 65 50

Nutsedge, Purple 0 0 30 25 20 0 5

Prickly Sida - 100 100 100 100 0 100

Purslane 100 100 100 100 100 70 100 Quackgrass 20 30 35 15 10 0 35

Ragweed - 100 - 90 100 70 100

Russian Thistle - 80 - - 0 0 100

Ryegrass, It 15 35 20 20 10 0 30

Sandbur 50 25 100 35 75 0 25

Signalgrass 95 65 100 80 90 30 20

Sowthistle - 100 100 100 100 100 -

Spanishneedles - 100 - 100 100 50 100

Surinam Grass 100 100 100 95 95 10 80

Table C Compounds

16 g ai/ha 2 3 4 5 6 14 15 27 149 150

Preemergence

Barnyardgrass 70 40 10 30 0 20 20 0 10 20

Bermudagrass 50 65 25 70 60 50 60 0 0 15

Black Mustard 0 0 0 50 0 65 0 25 0 0

Bluegrass 30 20 10 20 30 35 15 0 0 0

Chickweed - 100 100 100 - - 65 95 - -

Crabgrass, Lg 98 65 75 80 90 20 75 75 50 0

Crabgrass, Nk - 100 98 98 - 100 98 0 0 90

Dallisgrass 75 10 15 40 50 50 95 0 0 0

Dayflower, VA 98 50 50 95 - 100 0 70 0 100

Field Bindweed - 100 100 95 100 100 100 100 70 60

Foxtail, Green 35 95 20 60 20 15 10 20 0 15

Goosegrass 35 35 0 0 15 0 0 0 0 0

Groundsel - - - - - - 100 95 - -

Guineagrass - 100 100 90 75 100 75 75 20 100

Itchgrass 50 20 20 50 30 0 0 25 0 20

Johnsongrass 35 75 25 75 30 70 50 65 20 0

Kochia - 98 85 100 75 100 25 0 0 90

Mallow - - 100 100 90 98 85 100 95 95

Morningglory 60 - 65 100 - 100 20 70 65 -

Nutsedge, Purple 0 20 0 20 0 20 0 0 0 5

Prickly Sida - 100 100 100 100 100 100 100 0 100

Purslane 70 100 100 95 100 100 100 98 0 60

Quackgrass 10 25 25 25 0 0 0 0 0 0

Ragweed - 90 80 95 95 - 90 0 70 60

Russian Thistle - - - 0 0 - - 0 0 100

Ryegrass, It 0 25 15 50 15 15 0 0 0 25 Sandbur 20 10 10 95 0 0 0 0 0 0

Signalgrass 75 98 60 65 25 0 65 10 20 0

Sowthistle - 100 90 100 100 100 95 98 65 -

Spanishneedles - 100 60 90 100 - 100 100 50 100

Surinam Grass 100 100 100 100 100 70 95 35 0 80

Table C Compounds

8 g ai/ha 2 3 4 5 6 14 15 27 149 150

Preemergence

Barnyardgrass 70 25 10 10 0 10 0 0 10 20

Bermudagrass - 65 15 20 0 20 40 0 0 0

Black Mustard - 0 0 0 0 20 0 0 0 0

Bluegrass 10 10 0 10 0 35 0 0 0 0

Chickweed - 100 100 98 - - 65 95 - -

Crabgrass, Lg 25 40 30 60 35 10 50 50 0 0

Crabgrass, Nk - 75 0 98 - 98 0 0 0 60

Dallisgrass 35 0 0 25 0 0 65 0 0 0

Dayflower, VA 98 0 0 20 - 60 0 0 0 100

Field Bindweed - 95 80 80 80 100 65 100 60 60

Foxtail, Green 35 25 10 0 0 0 10 0 0 0

Goosegrass 30 0 0 0 0 0 0 0 0 0

Groundsel - - - - - - 35 65 - -

Guineagrass - 100 70 0 0 25 75 65 0 0

Itchgrass 25 20 10 40 0 0 0 0 0 0

Johnsongrass - 30 0 35 30 0 50 - 20 0

Kochia - 65 85 20 20 100 0 0 0 0

Mallow - - 100 100 65 40 75 98 50 50

Morningglory 60 98 60 75 50 100 0 70 35 0

Nutsedge, Purple 0 0 0 0 0 0 0 0 0 0

Prickly Sida - 100 100 100 25 100 100 90 0 50

Purslane 70 100 90 95 65 100 98 90 0 0

Quackgrass 0 0 0 15 0 0 0 0 0 0

Ragweed - 65 60 70 0 - 0 0 0 35

Russian Thistle - - 0 - 0 - 0 0 0 100

Ryegrass, It 0 25 0 0 0 0 0 0 0 -

Sandbur - - 0 10 0 0 0 0 0 0

Signalgrass 75 90 10 25 25 0 25 0 0 0

Sowthistle - 90 90 100 100 100 35 0 - -

Spanishneedles - 70 - - - - 100 50 35 65 Surinam Grass 100 100 98 100 25 10 70 30 - 0

Table C Compounds Table C Compounds

4 g ai/ha 3 4 5 149 150 4 g ai/ha 3 4 5 149 150

Preemergence Preemergence

Barnyardgrass 0 0 0 0 0 Kochia 0 0 0 0 0

Bermudagrass 0 0 0 0 0 Mallow - 0 - - 0

Black Mustard 0 0 0 0 0 Morningglory 90 0 70 35 0

Bluegrass 0 0 0 0 0 Nutsedge, Purple 0 0 0 0 -

Chickweed 100 100 98 - - Prickly Sida 100 35 75 0 50

Crabgrass, Lg 35 0 60 0 0 Purslane 0 0 - 0 0

Crabgrass, Nk 75 0 0 0 35 Quackgrass 0 0 0 0 0

Dallisgrass 0 0 0 0 0 Ragweed 65 50 50 0 -

Dayflower, VA 0 0 0 0 100 Russian Thistle - 0 0 0 0

Field Bindweed 70 30 40 0 - Ryegrass, It 0 0 0 0 15

Foxtail, Green 25 0 0 0 0 Sandbur - 0 - 0 0

Goosegrass 0 0 0 0 0 Signalgrass 15 0 20 0 0

Guineagrass 75 0 - 0 - Sowthistle - 0 50 0 -

Itchgrass 20 0 0 0 0 Spanishneedles 65 25 0 0 0

Johnsongrass 0 0 0 0 0 Surinam Grass 50 0 35 0 0

Table C Compounds Table C Compounds

2 g ai/ha 3 4 5 2 g ai/ha 3 4 5

Preemergence Preemergence

Barnyardgrass 0 0 0 Kochia 0 0 0

Bermudagrass 0 0 0 Mallow - 0 -

Black Mustard 0 0 0 Morningglory 0 0 -

Bluegrass 0 0 0 Nutsedge, Purple 0 0 0

Chickweed 100 25 98 Prickly Sida 0 0 65

Crabgrass, Lg 35 0 30 Purslane - 0 0

Crabgrass, Nk 75 0 0 Quackgrass 0 0 0

Dallisgrass 0 0 0 Ragweed 65 0 50

Dayflower, VA 0 0 0 Russian Thistle - 0 0

Field Bindweed 70 0 20 Ryegrass, It 0 0 0

Foxtail, Green 0 0 0 Sandbur - 0 0

Goosegrass 0 0 0 Signalgrass 0 0 0

Guineagrass 0 0 - Sowthistle 0 0 0

Itchgrass 0 0 0 Spanishneedles 60 0 0

Johnsongrass 0 0 0 Surinam Grass 0 0 0 TEST D

Seeds of plant species selected from wheat (Triticum aestivum), corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), wild poinsettia (poinsettia, wild; Euphorbia heterophylla), palmer amaranth (Amaranthus palmeri), waterhemp (Amaranthus rudis), ladysthumb smartweed (smartweed; Polygonum persicaria), Surinam grass (Brachiaria decumbens), large crabgrass (crabgrass, lg; Digitaria sanguinalis), Brazilian crabgrass (crabgrass, Br; Digitaria horizontalis), fall panicum (panicum, fall; Panicum dichotomiflorum), giant foxtail (foxtail, giant; Setaria faberii), green foxtail (foxtail, green; Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), ragweed (Ambrosia elatior), pigweed (Amaranthus retroflexus), barnyardgrass (Echinochloa crus-galli), sandbur (Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), Italian ryegrass (ryegrass, It; Lolium multiflorum), dayflower (dayflower, VA; Commelina virginica), field bindweed (Convolvulus arvensis), cocklebur (Xanthium strumarium), morningglory (Ipomoea coccinea), nightshade (Solanum ptycanthum), kochia (Kochia scoparia), yellow nutsedge (nutsedge, yellow; Cyperus esculentus) and hairy beggarticks (hairy beggar; Bidens pilosa), were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants from these crop and weed species were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Postemergence results at 0.5, 1, 2, 4, and 8 g ai/ha are the mean of three replicates for compounds 5, 20 and 126.

Table D Compound Table D Compound

31 g ai/ha 14 16 g ai/ha 14

Postemergence Postemergence

Corn 100 Corn 100

Crabgrass, Lg 98 Crabgrass, Lg 98

Foxtail, Giant 100 Foxtail, Giant 100

Goosegrass 100 Goosegrass 100

Johnsongrass 100 Johnsongrass 100

Lambsquarters 100 Lambsquarters 100

Pigweed 100 Pigweed 100

Ragweed 100 Ragweed 100

Soybean 100 Soybean 100 Surinam Grass 100 Surinam Grass 100

Velvetleaf 100 Velvetleaf 100

Wheat 100 Wheat 100

Table D Compounds

8 σ ai/ha 5 14 20 24 55 126

Postemergence

Arrowleaf Sida - - - 75 90 -

Barnyardgrass - - - 100 100 -

Corn 78 90 68 40 100 38

Crabgrass, Br - - - 65 98 -

Crabgrass, Lg 90 85 85 - - 73

Dayflower, VA - - - 98 98 -

Field Bindweed - - - 100 90 -

Foxtail, Giant 100 100 100 - - 100

Goosegrass 77 100 78 - - 75

Hairy Beggar - - - 100 100 -

Johnsongrass 87 100 100 - - 98

Lambsquarters 100 100 100 - - 100

Palmer Amaranth - - - 100 100 -

Panicum, Fall - - - 85 100 -

Pigweed 100 100 100 - - 100

Poinsettia, Wild - - - 100 100 -

Ragweed 100 100 100 - - 100

Ryegrass, It - - - 50 65 -

Sandbur - - - 100 100 -

Smartweed - - - 100 100 -

Soybean 100 98 100 98 100 99

Surinam Grass 98 100 98 - - 88

Velvetleaf 100 100 100 - - 100

Waterhemp - - - 100 100 -

Wheat 100 100 100 - - 100

Table D Compounds

4 g ai/ha 5 14 20 24 55 126

Postemergence

Arrowleaf Sida - - - 65 80 -

Barnyardgrass - - - 98 100 -

Corn 23 25 25 35 30 23 Crabgrass, Br - - - 65 75 -

Crabgrass, Lg 73 75 70 - - 70

Dayflower, VA - - - 95 98 -

Field Bindweed - - - 100 90 -

Foxtail, Giant 99 100 92 - - 92

Goosegrass 65 65 74 - - 77

Hairy Beggar - - - 100 100 -

Johnsongrass 93 100 97 - - 97

Lambsquarters 100 100 100 - - 100

Palmer Amaranth - - - 100 100 -

Panicum, Fall - - - - 98 -

Pigweed 100 100 100 - - 100

Poinsettia, Wild - - - 100 100 -

Ragweed 100 100 100 - - 95

Ryegrass, It - - - 35 40 -

Sandbur - - - 75 90 -

Smartweed - - - 100 100 -

Soybean 100 95 98 95 98 83

Surinam Grass 78 100 94 - - 77

Velvetleaf 100 100 100 - - 98

Waterhemp - - - 100 100 -

Wheat 93 90 90 - - 100

Table D Compounds

2 g ai/ha 5 14 20 24 55 126

Postemergence

Arrowleaf Sida - - - 65 75 -

Barnyardgrass - - - 98 98 -

Corn 15 25 25 20 10 20

Crabgrass, Br - - - 65 60 -

Crabgrass, Lg 52 70 75 - - 62

Dayflower, VA - - - 80 75 -

Field Bindweed - - - 100 80 -

Foxtail, Giant 83 75 97 - - 75

Goosegrass 40 60 45 - - 67

Hairy Beggar - - - 100 100 -

Johnsongrass 86 100 92 - - 87

Lambsquarters 99 100 100 - - 95

Palmer Amaranth - - - 100 100 - Panicura, Fall - - - 70 98 - Pigweed 100 100 100 - - 100

Poinsettia, Wild - - - 100 100 -

Ragweed 100 100 95 - - 88

Ryegrass, It - - - 30 20 -

Sandbur - - - 40 80 -

Smartweed - - - 100 100 -

Soybean 85 80 80 95 90 63

Surinam Grass 77 75 63 - - 52

Velvetleaf 100 100 100 - - 98

Waterhemp - - - 80 100 -

Wheat 62 75 43 - - 83

Table D Compounds

125 g ai/ha 20 24 28 32 56 94 126 142 143

Preemergence

Arrowleaf Sida - 100 100 100 - 100 100 - 65

Barnyardgrass - 70 50 80 - 70 98 - 35

Cocklebur - 100 - 100 - 10 100 - -

Corn 0 60 30 20 10 25 40 30 0

Crabgrass, Br - 100 90 100 - 100 100 - 75 Crabgrass, Lg 100 100 - 100 100 100 100 100 98 Dayflower, VA - 100 100 95 - 100 100 - 98 Field Bindweed - 100 100 100 - 95 100 - 100 Foxtail, Giant 70 80 90 70 100 90 100 100 50 Foxtail, Green - 98 75 90 - 100 100 - 95 Goosegrass 98 65 40 95 98 98 95 95 35 Johnsongrass 95 98 75 98 95 95 100 70 65 Kochia - 100 100 100 - 100 100 - 100

Lambsquarters 100 100 100 100 100 100 100 100 100 Morningglory - 95 100 100 - 80 100 - 65 Nightshade - 100 100 100 - 100 100 - 100 Nutsedge, Yellow - 65 0 65 - 50 35 - 80 Palmer Amaranth - 100 100 100 - 100 100 - 100 Panicum, Fall - 98 100 98 - 98 100 - 98 Pigweed 100 - - - 100 - - 100 -

Poinsettia, Wild - 75 100 100 - 100 100 - 100 Ragweed 100 100 100 100 100 100 98 70 30 Ryegrass, It - 60 35 60 - 70 70 - 75 Sandbur - 60 95 100 - 95 100 - 100

Smartweed - 100 - 98 - - 100 - -

Soybean 100 50 0 65 60 25 75 75 0

Surinam Grass 100 90 100 100 95 80 100 98 95

Velvetleaf 100 100 100 100 100 100 100 100 95

Waterhemp - 100 100 100 - 100 100 - 100

Wheat 98 - - - 40 - - 25 -

Table D Compounds

62 g ai/ha 20 24 28 32 56 94 126 142 143

Preemergence

Arrowleaf Sida - 98 100 100 - 80 100 - 50

Barnyardgrass - 50 35 50 - 35 60 - 35

Cocklebur - 100 0 100 - 0 25 - -

Corn 0 15 0 15 10 25 30 25 0

Crabgrass, Br - 100 90 100 - 95 100 - 75

Crabgrass, Lg 100 100 - 100 100 98 98 100 50

Dayflower, VA - 100 100 75 - 100 100 - 70

Field Bindweed - 98 65 100 - 80 100 - 98

Foxtail, Giant 70 70 40 - - 30 60 100 15

Foxtail, Green - 65 10 90 - 95 75 - 40

Goosegrass 90 65 10 65 65 60 70 90 0

Johnsongrass 75 80 50 70 65 65 75 35 50

Kochia - 100 100 60 - 98 100 - 70

Lambsquarters 100 90 95 100 100 80 100 100 100

Morningglory - 75 35 85 - 80 65 - 30

Nightshade - 100 100 100 - 100 100 - 100

Nutsedge, Yellow - 50 0 35 - 0 35 - 0

Palmer Amaranth - 100 100 100 - 100 100 - 100

Panicum, Fall - 98 95 98 - 50 100 - 50

Pigweed 100 - - - 100 - - 100 -

Poinsettia, Wild - 75 100 100 - 100 100 - 80

Ragweed 90 98 90 90 80 25 95 60 30

Ryegrass, It - 50 30 40 - 50 40 - 25

Sandbur - 40 90 35 - 65 65 - 20

Smartweed - 65 - - - - 98 - -

Soybean 60 50 0 20 40 25 50 25 0

Surinam Grass 98 80 70 70 80 20 65 - 20

Velvetleaf 100 100 100 100 100 95 100 95 95 Waterhemp - 100 100 100 - 100 100 - 100

Wheat 35 - - - 30 - - 20 -

Table D Compounds

31 g ai/ha 20 24 28 32 56 94 126 142 143

Preemergence

Arrowleaf Sida - 65 30 100 - 80 80 - 0

Barnyardgrass - 35 25 30 - 20 25 - 15

Cocklebur - 0 0 100 - - - - -

Corn 0 0 0 0 0 0 20 0 0

Crabgrass, Br - 95 90 98 - 95 95 - 60

Crabgrass, Lg 100 65 100 95 100 95 95 100 50

Dayflower, VA - 80 80 75 - 90 100 - 0

Field Bindweed - 98 35 100 - 65 75 - 50

Foxtail, Giant 70 40 30 20 90 10 40 35 0

Foxtail, Green - 20 - 75 - 30 40 - 0

Goosegrass 70 30 0 40 20 0 70 70 0

Johnsongrass 65 65 10 70 40 35 40 35 10

Kochia - 100 60 50 - 95 98 - 40

Lambsquarters 100 90 30 100 100 50 85 100 100

Morningglory - 65 0 35 - 50 40 - 20

Nightshade - 100 100 100 - 100 100 - 100

Nutsedge, Yellow - 0 0 35 - 0 35 - 0

Palmer Amaranth - 100 100 100 - 100 100 - 80

Panicum, Fall - 98 60 85 - 0 100 - 0

Pigweed 100 - - - 100 - - 100 -

Poinsettia, Wild - 75 100 40 - 65 60 - 70

Ragweed 60 98 80 0 70 25 95 50 0

Ryegrass, It - 20 0 0 - 10 40 - 0

Sandbur - 0 75 35 - 20 0 - 0

Smartweed - 0 - 98 - - 98 - -

Soybean 60 40 0 0 20 0 50 0 0

Surinam Grass 40 20 0 65 50 20 65 90 0

Velvetleaf 100 80 70 100 50 50 95 60 35

Waterhemp - 100 100 75 - 100 100 - 30

Wheat - - - - 0 - - 0 -

Table D Compounds

16 g ai/ha 20 24 28 32 56 94 126 142 143 Preemergence

Arrowleaf Sida - 30 0 70 - 0 65 - 0

Barnyardgrass - 15 0 20 - 0 25 - 0

Cocklebur - - - 85 - - - - 0

Corn 0 0 0 0 0 0 0 0 0

Crabgrass, Br - 35 25 65 - 0 95 - 20

Crabgrass, Lg 98 20 100 70 98 80 40 85 20

Dayflower, VA - - 0 65 - 0 95 - 0

Field Bindweed - 70 0 85 - 20 65 - 0

Foxtail, Giant 0 35 0 15 25 0 15 - 0

Foxtail, Green - 15 0 5 - 5 15 - 0

Goosegrass 20 0 0 40 0 0 40 40 0

Johnsongrass 0 40 10 20 30 0 0 10 0

Kochia - 40 40 40 - 40 65 - 0

Lambsquarters 40 80 30 60 100 - 50 100 0

Morningglory - 35 0 35 - 0 30 - 0

Nightshade - 100 100 95 - 100 100 - 90

Nutsedge, Yellow - 0 0 0 - 0 0 - 0

Palmer Amaranth - 100 80 100 - 70 90 - 40

Panicum, Fall - 65 0 75 - 0 95 - 0

Pigweed 70 - - - 65 - - 100 -

Poinsettia, Wild - 75 50 40 - - 60 - 0

Ragweed 15 75 30 0 70 - 0 20 0

Ryegrass, It - 0 0 0 - 0 20 - 0

Sandbur - 0 0 0 - 10 0 - 0

Smartweed - - - 95 - - 95 - -

Soybean 50 15 0 0 0 0 50 0 0

Surinam Grass 20 0 0 10 20 0 10 10 0

Velvetleaf 65 50 20 70 50 30 85 0 0

Waterhemp - 100 100 - - 100 100 - -

Wheat 0 - - - 0 - - 0 -

Table D Compounds

8 g ai/ha 20 24 28 32 56 94 126 142 143

Preemergence

Arrowleaf Sida - 0 0 0 - 0 50 - 0

Barnyardgrass - 0 0 0 - 0 0 - 0

Cocklebur - 0 - 0 - 0 - - 0

Corn 0 0 0 0 0 0 0 0 0 Crabgrass, Br - 20 0 65 - 0 65 - 0

Crabgrass, Lg 75 0 0 50 25 35 30 - 0

Dayflower, VA - 50 0 65 - 0 0 - 0

Field Bindweed - 25 0 65 - 0 60 - 0

Foxtail, Giant 0 0 0 0 0 0 0 0 0

Foxtail, Green - 0 0 0 - 0 0 - 0

Goosegrass 0 0 0 0 0 0 0 35 0

Johnsongrass 0 5 0 0 0 0 0 0 0

Kochia - 20 0 30 - 0 30 - 0

Lambsquarters - 0 - 0 100 0 0 98 0

Morningglory - 35 0 20 - 0 30 - 0

Nightshade - 75 0 90 - 65 95 - 90

Nutsedge, Yellow - 0 0 0 - 0 0 - 0

Palmer Amaranth - 80 65 90 - 50 90 - 0

Panicum, Fall - 65 0 75 - 0 75 - 0

Pigweed 25 - - - 0 - - 75 -

Poinsettia, Wild - 35 35 0 - 30 0 - 0

Ragweed 0 20 0 0 60 0 0 0 0

Ryegrass, It - 0 0 0 - 0 0 - 0

Sandbur - 0 0 0 - 0 0 - 0

Smartweed - - - - - - 95 - -

Soybean 0 0 0 0 0 0 50 0 0

Surinam Grass 5 0 0 0 - 0 0 0 0

Velvetleaf 0 20 0 50 10 0 65 0 0

Waterhemp - 70 35 - - 35 80 - 0

Wheat 0 - - - 0 - - 0 -

TEST E

This test evaluated the effect of mixtures of Compound 5 with several commercial herbicides on two plant species. Seeds of plant species selected from giant foxtail (SETFA Setaria faberii) and velvetleaf (ABUTH Abutilon theophrasti) were planted approximately 1 cm deep into pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent and starter nutrients. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of about 16 hours; daytime and nighttime temperatures were about 24-30 °C and 19-21 °C, respectively. Balanced fertilizer was applied through the watering system. The plants were grown for 9 to 14 days to reach an appropriate stage of growth prior to application. Treatments consisted of Compound 5 and the commercial herbicides alone and in combination, suspended or dissolved in a non-phytotoxic solvent mixture which included a surfactant and applied as a foliage spray using a volume of 281 L/ha. Each treatment was replicated three times. Treated plants and controls were maintained in a greenhouse and watered as needed with care to not wet the foliage for the first 24 hours. After 14 days, treated plants were compared to controls and visually evaluated. Plant response ratings, calculated as the mean of the three replicates, are summarized in Table E, and are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Colby's Equation was used to determine the expected herbicidal effects from the mixtures. Colby's Equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:

Pa ₊b = Pa + Pb - (PaP _b 100)

wherein P _a+¾ is the percentage effect of the mixture expected from additive contribution of the individual components:

P _a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and

P¾ is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

In Table E, the "Obsd" value is the observed effect and the "Exp." value is the expected effect calculated from Colby's Equation.

Table El - Observed and Expected Results from Compound 5 Alone and in Combination

with Glyphosate

Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Glyphosate Obsd. Exp. Obsd. Exp.

0.125 5 65

0.25 5 77

62 60 35

125 72 72

0.125 62 45 77

0.125 125 50 90

0.25 62 58 85

0.25 125 68 93 Table E2 - Observed and Expected Results from Compound 5 Alone and in Combination with Glyphosate

Table E3 - Observed and Expected Results from Compound 5 Alone and in Combination with Aminocyclopyrachlor

Table E4 - Observed and Expected Results from Compound 5 Alone and in Combination with Quizalofop-P-ethyl

Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Quizalofop-P- Obsd. Exp. Obsd. Exp.

ethyl

0.25 5 77

0.75 22 100

4 90 0

0.25 4 90 91 73 77

0.75 4 90 92 98 100 Table E5 - Observed and Expected Results from Compound 5 Alone and in Combination with Sulfometuron-methyl

Table E6 - Observed and Expected Results from Compound 5 Alone and in Combination with Glyphosate

Table E7 - Observed and Expected Results from Compound 5 Alone and in Combination with Glyphosate

Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Glyphosate Obsd. Exp. Obsd. Exp.

0.25 5 77

0.75 22 100

16 0 0

31 37 0

0.25 16 8 5 73 77

0.25 31 43 40 86 77 Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Glyphosate Obsd. Exp. Obsd. Exp.

0.75 16 25 22 100 100

0.75 31 40 50 100 100

Table E8 - Observed and Expected Results from Compound 5 Alone and in Combination with Aminocyclopyrachlor

Table E9 - Observed and Expected Results from Compound 5 Alone and in Combination with Sulfometuron-methyl

Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Sulfometuron- Obsd. Exp. Obsd. Exp.

methyl

0.5 35 88

1 70 100

0.25 10 53

3 75 95

0.5 0.25 37 42 81 95

0.5 3 60 84 97 99

1 0.25 68 73 100 100

1 3 68 93 98 100 Table E10 - Observed and Expected Results from Compound 5 Alone and in Combination with Metsulfuron-methyl

Observed and Expected Results from Compound 5 Alone and in Combination with Quizalofop-P-ethyl

Table E12 - Observed and Expected Results from Compound 5 Alone and in Combination with Glyphosate

Application Rate (g a.i./ha) SETFA ABUTH

Cmpd 5 Glyphosate Obsd. Exp. Obsd. Exp.

0.5 35 88

1 70 100

250 95 87

500 99 88

0.5 250 75 97 97 98

0.5 500 95 100 97 99

1 250 75 99 100 100

1 500 88 100 100 100

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