TITLE HERBICIDAL FYRROLESULFONYLUREAS

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of U.S.S.N. 07/573,074 filed August 29, 1990.

BACKGROUND OF THE INVENTION

The present invention relates to herbicidal pyrrolesulfonylureas, compositions thereof and a method for their use as preemergence and/or postemergence herbicides or plant growth regulants. New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few.

Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, -SO2NHCONH-, linking two aromatic or heteroaromatic rings.

U.S. 4,368,067 discloses herbicidal sulfonylureas of the formula

wherein:

Rl is H, C1-C4 alkyl, N0 ₂ , CN, C(0)CC1 ₃ , S0 ₂ Rn, C(0)R ₅ or

C0 ₂ H;

R ₂ is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, Cl or Br;

R4 is H, C1-C4 alkyl, cyanoethyl, C5-C6 cycloalkyl, benzyl, phenyl substituted with Cl or N0 , or C(0)Rg;

R5 is C1-C4 alkyl or C1-C4 alkoxy;

Rg is C1-C4 alkyl, C1-C4 alkoxy or NR Rg; and R7 and Rg are independently Cι-C ₂ alkyl.

U.S. 4,549,898 discloses herbicidal sulfonamides of the formula

wherein:

X is O, S, NR4 or -C(Rδ)=N-;

R ₂ is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, N0 ₂ , C1-C3 alkoxy, C(W)R ₈ , S0 ₂ NR ₆ R7, S(0) _n -Cι-C ₃ alkyl or C(0)R ₉ ; R4 is H, C1-C4 alkyl, C1-C4 cyanoalkyl, C3-C5 cycloalkyl, benzyl,

C(0)Cι-C4 alkoxy, C(0)NR ₆ R ₇ or C(0)Cι-C4 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms; Rg is H, Cχ-C6 alkyl, C1-C4 cyanoalkyl, OCH3 or OCH2CH3;

R7 is H, CI-CQ alkyl or C3-Cg alkenyl; or Rg and R7, together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated heterocyclic ring which may contain an oxygen; and Y is O or S. .

EP-A-126,711 discloses herbicidal sulfonamides of the formula

wherein: Q is halogen, C1-C alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, N0 ₂ , NH ₂ , C1-C4 alkylamino, C1-C4 dialkylamino, CN, C1-C4 alkoxycarbonyl, CHO, C ₂ -C4 alkoxyalkyl, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkenyl or C1-C4 alkynyl; Ri is H, halogen, NO2, CRg(OCι-C4 alkyl)2,

C. (C ₃ -C ₅ alkylene), C(W)R ₆ ,

S0 ₂ NR ₇ R ₈ , C(0)R ₉ or ODmRio; X is O, S, NR5, C(R ₅ )=N, CH=CH or

R5 is H, C1-C4 alkyl or C3-C4 alkenyl.

EP-A-161,211 discloses herbicidal stdfonamides of the formula

wherein: G is

Q is O, S or NR ⁷ ;

A is O, S, SO, S0 ₂ or -(CRι ₀ Rii) _m -; mis 0, 1 or 2;

Η is H, C1-C4 alkyl, C3-C cycloalkyl, benzyl or phenyl; and RlO and RU are independently H or C1-C4 alkyl.

SUMMARY OF THE INVENTION The invention comprises compounds of Formula I, agriculturally suitable compositions thereof and a method of use as preemergence and/or postemergence herbicides or plant growth regulants.

W II JSWJJNHCNA

R

wherein: J is

J-l J-2 J-3

W is O or S; R is H or CH3;

R ¹ is H; CH _3; CH ₂ OCH _3; CH2OC2H5. CH ₂ CN _; CH ₂ SCH ₃ ,

CH2SC2H5; C ₂ -Cg alkyl optionaUy substituted with one Cι-C alkoxy, Cι-C ₂ alkylthio, CN or one or more halogens; C3-C4 alkenyl; C3-C4 haloalkenyl; C3-Cg cycloalkyl; C(0)R ⁵ ; N(CH ₃ ) ₂ ; or Ql;

R2 is C1-C4 alkyl optionally substituted with one CN, C2-C3 alkylcarbonyl, methoxycarbonyl, Cι-C ₂ alkoxy, Cι-C alkylthio, C1-C2 alkylsulfonyl, S(0) ₂ NR ⁶ R ⁷ , OH or one or more halogens; C2-C4 alkenyl optionally substituted with one Cι-C ₂ alkoxy, Cι-C ₂ alkylthio, CN or one or more halogens; (CH ₂ ) _m ² ; CN; C(0)R8; C(0)0R9; C(O)NR10RH; CCR^NOR ¹³ ; CCR^XOR^XO ¹⁶ ); S(0) _n R ¹⁷ ; S(0) ₂ NR ¹⁸ R ¹⁹ ; N0 ₂ ; halogen or OR ⁷³ ;

R ³ is H, halogen or C1-C4 alkyl;

R ⁴ is H, C1-C4 alkyl optionally substituted with one CN, C2-C3 alkylcarbonyl, methoxycarbonyl, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfonyl, S(0)2NR ⁶ R ⁷ , OH or one or more halogens; C2-C4 alkenyl optionally substituted with one C1-C2 alkoxy, C1-C2 alkylthio, CN or one or more halogens; CN; C(0)Rδ; C(0)OR ⁹ ; C(O)NR10RU; C(R ¹² )=NOR ¹³ ;

S(0) _n R ¹⁷ ; S(0) ₂ NR ¹⁸ R ¹⁹ ; or halogen;

Rδ is C1-C4 alkyl, C1-C4 alkoxy or NR20R21 _;

R ⁶ is H, Cι-C ₂ alkyl or OCH3;

R ⁷ is C1-C2 alkyl; or R6 and R ⁷ can be taken together as -(CH2)3- or- (CH2)4

R° is H, C1-C3 alkyl or cyclopropyl;

R ⁹ is CH3; C2-C3 alkyl optionally substituted with one C1-C2 alkoxy, OH, CN or one or more halogens; C3-C4 alkenyl; or propargyl; R ^χ 0 is H, C1-C3 alkyl or OCH3;

R ¹¹ is C1-C3 alkyl; or

R ¹⁰ and R ¹¹ can be taken together as -(CH )3-, -(CH2)4-, -(CH2>5- or -(CH ₂ )2θ(CH ₂ )2-; R ¹² is H, C1-C3 alkyl, allyl, halogen, CN, N3, C1-C2 alkoxy, C1-C2 alkylthio or SCN;

R ¹³ is C1-C3 alkyl or allyl;

R ¹⁴ is H or C1-C3 alkyl; Rl5 and IG are independently C1-C2 alkyl; * ⁷ is C1-C4 alkyl, optionally substituted with one C1-C2 alkoxy, C1-C2 alkylthio, CN or one or more halogens; C3.C4 alkenyl; or cyclopropylmethyl; Rl8 is H, C1-C3 alkyl or OCH3;

R ¹⁹ is H or C1-C2 alkyl; or

R ¹⁸ and R ¹⁹ can be taken together as -(CH ₂ >3-, -(CH ₂ )4- or

-(CH ₂ ) ₅ -; R20 and R21 QJ-Q independently Cι-C ₂ alkyl; or R ²⁰ and R ²¹ can be taken together as -(CH )3-, -(CH ₂ )4-, -(CH >5- or -(CH ₂ )2θ(CH ₂ )2-; R ⁷¹ is H, halogen or CF3;

R ⁷³ is C1-C4 alkyl optionally substituted with one or more halogens, CN, C C ₂ alkoxy, or C C ₂ alkylthio; C(0)R ⁷⁴ ; S0 ₂ R ⁷ 5; C3-C4 alkenyl; or propargyl; R ⁷⁴ is C1-C4 alkyl optionally substituted with C1-C2 alkoxy, one or more halogens, or CN; C3-C4 alkenyl; or C1-C3 alkoxy;

R ⁷⁵ is C C ₃ alkyl or CF3; m is 0 or 1; n is 0, 1 or 2;

Q1 is phenyl, phenyl substituted with one to two groups selected from halogen and CH3, a fully unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from

0-1 S, 0-1 O and 0-4 N and a fully unsaturated 5- or 6- membered heterocyclic ring substituted with one to two groups selected from C1-C4 alkyl, C3-C4 alkenyl, halogen, C1-C3 alkoxy, Cι-C haloalkoxy, C1-C3 alkylthio, C3-C4 alkenylthio and Cj-C ₂ haloalkylthio, said Q bound through a carbon atom;

Q ² is phenyl, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O and 0-2 S, a partially saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N, a fully unsaturated 5- or

6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N, phenyl substituted with one to two groups selected from halogen and CH3, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from

0-2 O and 0-2 S substituted with one to two C1-C3 alkyl

groups, a partially saturated heterocycUc ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N substituted with one to two C1-C3 alkyl groups, and an unsaturated 5- or

6-membered heterocycUc ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N substituted with one to two groups selected from C1-C4 alkyl, C3-C4 alkenyl, halogen,

C1-C3 alkoxy, Cι-C ₂ haloalkoxy, C1-C3 alkylthio, C3-C4 alkenylthio and Cι-C ₂ haloalkylthio;

A is

A-l A-2 A-3

A-4

A-5 A-6

A-7

X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alkylthio, halogen, C ₂ - C5 alkoxyalkyl, C ₂ -C5 alkoxyalkoxy, amino, C1-C3 alkylamino or di(Cι-C3 alkyDamino; Y is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy, amino, C1-C3 alkylamino, di(Cι-C3 alkyDamino, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkylthioalkyl, C - C5 alk lsulfinylalkyl, C2-C5 alkylsulfonylalkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C3-C5 cycloalkyl, azido, cyano,

or N(OCH ₃ )CH ₃ ; p is 2 or 3;

Q ³ and Q ⁴ are independently O or S; R ²² is H or C1-C3 alkyl;

R23 and R ²⁴ are independently C1-C3 alkyl;

Z is CH or N;

Zl is CH or N;

Yi is O or CH^, Xl is CH3, OCH3 or OCF ₂ H;

X ² is CH3, CH ₂ CH ₃ or CH ₂ CF ₃ ;

Y ² is OCH3, OCH ₂ CH ₃ , SCH3, SCH ₂ CH ₃ , CH3 or CH ₂ CH ₃ ;

X ³ is CH3 or OCH3;

Y ³ is H or CH3; X ⁴ is CH3, OCH3, OCH ₂ CH ₃ , CH ₂ OCH ₃ or Cl; and

Y ⁴ is CH3, OCH3, OCH2CH3 or Cl; and their agriculturaUy suitable salts;

provided that:

(a) when X and/or Y is C haloalkoxy, then Z is CH;

(b) when m is zero, Q ² is bound through carbon to the pyrrole ring in J;

(c) when X is F, Cl, Br or I, then Z is CH and Y is OCH3, OCH ₂ CH ₃ , N(OCH ₃ )CH ₃ , NHCH3, N(CH ₃ ) ₂ or OCF ₂ H;

(d) when W is S, then R is H, A is A-l and Y is CH3, OCH3, OCH ₂ CH ₃ , CH ₂ OCH ₃ , CH ₂ CH ₃ , CF3, SCH3, OCH ₂ CH=CH ₂ , OCH ₂ C=CH, OCH2CH2OCH3, CH(OCH ₃ ) ₂ or

(e) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of Q^ and Q ² for each is less than or equal to eight;

(f) when A is A-2, A-3, A-4, A-5 , A-6 or A-7, then R is H; (g) when J is J-l, A is A-l and X and/or Y is alkyl, then R ² is other than CN or N0 ₂ ;

(h) when J is J-l, A is A-2, A-3 or A-4 and R ¹ is C(0)R ⁵ , then R ² is other than alky and (i) when J is J-l, A is A-l and X and or Y is Cj haloalkoxy, then R ² is other than C(0)OR ⁹ .

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", includes straight chain and branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl and the different butyl isomers.

Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers.

Alkenyl includes straight chain and branched alkenes, e.g., 1- propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. Alkylsulfonyl includes methylsulfonyl and ethylsulfonyl.

Alkylthio, etc. are used analogously to the above examples.

Cycloalkyl includes cyclopropyl, cyclobut l, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in compound words such as

"haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fuUy substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH ₂ CH ₂ F, CF ₂ CF3 and

CH ₂ CHFC1.

The total number of carbon atoms in a substituent group is indicated by the Ci-Cj prefix where i and j are numbers from 1 to 6. For example, Cι-C ₂ alkylsulfonyl would designate methylsulfonyl through ethylsulfonyl; C ₂ -C3 alkoxycarbonyl would designate methoxy and ethoxy attached through a carbonyl radical.

Compounds of the invention preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are: 1. Compounds of Formula I wherein Q ^x is the fuUy unsaturated substituted or unsubstituted heterocycUc ring, and Q ^x is selected from pyridinyl, pyrimidinyl, thienyl, furanyl, 1,2,4- triazolyl, 1,2,3-thiadiazolyl, oxazolyl, thiazolyl, imidazolyl or tetrazolyl, and Q ² is the substituted or unsubstituted heterocycUc ring containing 1 to 2 heteroatoms or the substituted or unsubstituted partially saturated heterocycUc ring containing 1 to 2 heteroatoms and Q ² is elected from 1,3-dioxolanyl, 1,3-dioxanyl, pyridinyl, pyrimidinyl, thienyl, furanyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, oxazolyl, thiazolyl, imidazolyl or tetrazolyl.

Compounds of Preferred 1 wherein:

Q ¹ -! Q!-2 Q!-3

Ql.4 Q ^x -5 Q!-6

Q!-7 Q!-8 Q!-9

Qi-10 Q ¹ -!! Q ^x -12

_R 43

N-N // \

^N γ ^N

Q!-19

q is 0 or 1;

R ² 5 and R ²⁶ are independently H, CH3 or Cl;

R ²⁷ and R ²⁸ are independently H, F, or CH3;

^" R ²⁹ isH,CH ₃ orOCH3; R ³ 0 is H or CH3;

R ³¹ , R ³² and R ³³ are independently H, CH3 or OCH3;

R ³⁴ , R ³⁵ and ³ ^ are independently H, CH ₃ , CH ₂ CH ₃ , Cl, Br,

OCH ₃ or OCH ₂ CH ₃ ;

R ³⁷ isHorCι-C ₂ alkyl;

R ³⁸ is CH3;

R ³⁹ is H, Cι-C ₂ alkyl, OCH3 or SCH3; R ⁴⁰ is H, CH3 or CH ₂ CH ₃ ;

R ⁴¹ and R ⁴² are independently H or CH3;

R ⁴³ is H, CH3, CH ₂ CH ₃ or C3H7;

W ¹ is O or S; W ² is O, S or NR ⁴⁴ ; R ⁴⁴ is H or CH3;

Q is

Q2-4 Q -5 Q ² -6

Q -7 Q ² -8 Q -9

Q ² -10 Q ² -ll Q ² -12

Q ² -13 Q ² -14 Q ² -15

Q ² -16 Q ² -17 Q ² -18

Q2-19 Q ² -20 Q ² -21

r is 0 or 1;

R ⁴ 5 and R ⁴⁶ are independently H, CH3 or Cl;

R ⁴⁷ is H or C^ alkyl;

R ⁴⁸ is H or CH3; R ⁴⁹ and R ⁵⁰ are independently H or CH3 ;

R51 is H, CH3 or OCH3;

R52 is H or CH3;

R53 R54 and R^5 are independently H, CH3 or OCH3;

R ⁵⁶ , R ⁵⁷ and R58 are independently H, CH3, CH2CH3, Cl, Br, OCH3 or OCH2CH3;

Rδ ⁹ is H or Cι-C ₂ alkyl;

R60 is CH3;

R ^β l is H, Cι-C ₂ alkyl, OCH3 or SCH3;

R62 ig H, CH3 or CH ₂ CH ₃ ; R ⁶³ and R ⁶⁴ are independently H or CH3;

R65 is H, CH3, CH ₂ CH ₃ or C3H7;

W ³ is O or S; W is O, S or NR66; and 66 is H or CH ₃ .

3. Compounds of Preferred 2 wherein:

W is O;

R ¹ is H, Ci-Ce alkyl, allyl, CH ₂ OCH ₃ , CH ₂ OC ₂ H5, CH ₂ SCH ₃ phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C(0)OCH3 or C(0)N(CH ₃ ) ₂ ; X is Cι-C ₂ alkyl, Cχ-C ₂ alkoxy, F, Cl, Br, I, OCF ₂ H, CH F,

CF ₃ , OCH ₂ CH ₂ F, OCH ₂ CHF ₂ , OCH ₂ CF ₃ , CH ₂ C1 or CH ₂ Br; and Y is H, Cι-C ₂ alkyl, Cι-C alkoxy, CH ₂ OCH ₃ , CH2OCH2CH3, NHCH3, N(OCH ₃ )CH ₃ , N(CH ₃ ) ₂ , CF3, SCH3, OCH ₂ CH=CH ₂ , OCH ₂ C≡CH, OCH ₂ CH ₂ OCH ₃ ,

CH ₂ SCH ₃ , C(0)R ²² ,

OCF ₂ H, SCF2H, cyclopropyl, C≡CH or C=CCH3.

4. Compounds of Preferred 3 wherein: R ³ is H, CH3, Cl or Br; and

R ⁴ is H, Cι-C ₂ alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0) ₂ CH3, Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(O)NR ¹⁰ R ⁿ , C(R ¹² )=NOR ¹³ , C(Rl ⁴ )(ORl5)(OR ¹⁶ ), S(0) _n Rl ⁷ , S(0) ₂ NRl ⁸ R ¹⁹ , F, Cl or Br; R ⁸ is H or Cι-C ₂ alkyl;

R ⁹ is Cχ-C ₂ alkyl or CH ₂ CH ₂ C1; RlO is H or CH3; Rll is CH3; l is H, CH3, C ₂ H ₅ or Cl; Rl ³ is CH3;

Rl ⁴ is H or Cι-C ₂ alkyl;

l5 and R* ⁶ are CH ₃ ;

R ¹⁷ is C1-C2 alkyl; R ¹⁸ is H or CH3; R ¹⁹ is CH3; and n is 0 or 2.

5. Compounds of Preferred 4 wherein:

R ² is C1-C2 alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0) ₂ CH ₃ , Q ² , C(0)R ⁸ , C(0)OR ⁹ , CCOJNRiOR ¹¹ , C(R ¹² )=NOR ¹³ , C(R ¹⁴ )(OR15)(OR16 _)J S(0) _n R ¹⁷ , S(0) ₂ NR1 ⁸ R1 , F, Cl, Br or OR ⁷³ .

6. Compounds of Preferred 5 wherein: R is H; and R ⁷¹ is H.

7. Compounds of Preferred 6 wherein: J is J-l.

8. Compounds of Preferred 6 wherein: J is J-2.

9. Compounds of Preferred 6 wherein: J is J-3.

10. Compounds of Preferred 7 wherein:

R ² is C1-C2 alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH2SCH ₃ ,

CH ₂ S(0) ₂ CH ₃ , Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ , S(0) ₂ CH ₃ , S(0) ₂ C ₂ H ₅ , S(0) ₂ N(CH ₃ ) ₂ , C _r C ₂ alkoxy, OC(0)CH ₃ , or OS0 ₂ CH ₃ ;

R ⁴ is H, Cι-C ₂ alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH SCH ₃ ,

CH ₂ S(0) ₂ CH ₃ , Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ , S(0) ₂ CH ₃ , S(0) ₂ C ₂ H ₅ or S(0) ₂ N(CH ₃ ) ₂ ;

R ⁸ is C1-C2 alkyl;

R ⁹ is Cι-C ₂ alkyl; Q ² is Q -l, Q -4, Q ² -5, Q -6, Q ² -10, Q ² -ll, Q ² -20 or Q ² -21;

_R 45, R46, _R 49 _f R50, _R 56, _R 57 and Rδδ are H; R65 is CH3;

W ³ is S; and r is O.

11. Compounds of Preferred 8 wherein:

R ² is Cι-C ₂ alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0) ₂ CH ₃ , Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ , S(0) ₂ CH _3> S(0) ₂ C ₂ H ₅ , S(0) ₂ N(CH ₃ ) ₂ , C C ₂ alkoxy, OC(0)CH ₃ , or OS0 ₂ CH ₃ ;

R ⁴ is H, Cι-C ₂ alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0) ₂ CH3, Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ , S(0) ₂ CH ₃ or S(0) ₂ N(CH ₃ ) ₂ ; R ⁸ is C1-C2 alkyl; R ⁹ is Cι-C ₂ alkyl;

Q ² is Q ² -l, Q ² -4, Q ² -5, Q ² -6, Q -10, Q ² -ll, Q ² -20 or Q ² -21; R45, R46 _} R49, R50, R56, _R 57 _{and R} 58 ^ _H ;

R65 i _s CH3;

W ³ is S; and r is 0.

12. Compounds of Preferred 9 wherein:

R ² is C1-C2 alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0)2CH ₃₎ Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ ,

S(0) ₂ CH _3> S(0) ₂ C ₂ H ₅ , S(0) ₂ N(CH ₃ ) ₂ , C C ₂ alkoxy,

OC(0)CH ₃ , or OS0 ₂ CH ₃ ;

R ⁴ is H, Cι-C ₂ alkyl, CH ₂ CN, CH ₂ OCH ₃ , CH ₂ SCH ₃ ,

CH ₂ S(0) ₂ CH ₃ , Q ² , C(0)R ⁸ , C(0)OR ⁹ , C(0)N(CH ₃ ) ₂ , S(0) ₂ CH ₃ or S(0) ₂ N(CH ₃ ) ₂ ; R ⁸ is C1-C2 alkyl;

R ⁹ is C1-C2 alkyl;

Q ² is Q -l, ² -4, Q -5, Q ² -6, ² -10, Q -ll, Q -20 or Q ² -21; R45 _J R46 _> R49 _? R50 _? R56, _R 57 ^a _R 58 are H;

R65 is CH3; W ³ is S; and r is 0.

13. Compounds of Preferred 10 wherein:

A is A-l; X is CH3, OCH3, OCH ₂ CH ₃ , OCH ₂ CF ₃ or Cl; and

Y is CH3, OCH3, NHCH3 or N(CH ₃ ) ₂ .

14. Compounds of Preferred 11 wherein:

A is A-l; X is CH3, OCH3, OCH ₂ CH ₃ , OCH ₂ CF ₃ or Cl; and

Y is CH3, OCH3, NHCIΪ3 or N(CH ₃ ) ₂ .

15. Compounds of Preferred 12 wherein

A is A-l; X is CH3, OCH3, OCH ₂ CH ₃ , OCH ₂ CF ₃ or Cl; and

Y is CH3, OCH3, NHCH3 or N(CH ₃ ) ₂ .

Compounds of the invention specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:

Methyl 3-[[[[(4,6-dirnethoxy-2-pyrinudinyl)amino]carbonyl]- amino]sulfonyl]-l-methyl-lH-pyrrole-2-carboxylate;

Methyl 3-[[[[[4-ethoxy-6-(methylamino)-l,3,5-triazin-2-yl]- amino]carbonyl]amino]-sulfonyl]-l-methyl-lH-pyrrole-2- carboxylate; N -[[(4-ethyl-6-methoxy-l,3,5-triazin-2-yl)-amino]carbonyl]- N ² ,N ² , 1-trimethyl- lH-pyrrole-2 ,3-disulfonamide ; N ³ -[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-

N ² ,N ² ,l-trimethyl-lH-pyrrole-2,3-disulfonamide; Methyl l-ethyl-2-[[[[(4-πιethoxy-6-nιethyl-l,3,5-triazin-2-yl)-a nιino]- carbonyl]amino]sulfonyl]-lH-pyrrole-3-carboxylate; 2-(ethylsulfonyl)-N-[[(4-methoxy-6-methyl-l ,3 ,5-triazin-2-yl)amino]- carbonyl]-l-methyl-lH-pyrrole-3-sulfonamide; and

2-[[[[(4,6-dimethoxy-2 pyrimidinyl)an_ήno]carbonyl]-amino]sulfonyl]- N,N,l-trimethyl-lH-pyrrole-3-carboxamide.

The invention also comprises novel compounds, such as the bromopyrrolesulfonamides of Formula II, useful as intermediates to the compounds of Formula I.

wherein:

R67 is H, C(CH ₃ ) ₃ or Si(CH3) ₂ C(CH ₃ )3; and ⁷ 2 is H or Si(CH(CH ₃ ) ₂ )3.

Another embodiment of the invention is the process for preparing any of the above compounds, said process comprising reacting

(a) the compounds of Equation 1 in an inert polar aprotic solvent for 5 minutes to 24 hours or more at 20° to 80°C

J-S0 NCO + R-NH-A — > I ; or 2. . 2

(b) the compounds of Equation 2 in an inert solvent followed by treatment with aqueous acid

O

II

J-S0 ₂ NH ₂ + R ^β δOCNR-A — > I ; or έ 5

(c) the compounds of Equation 3 in an inert solvent for 0.5 to 24 hours

O

J-Sθ2NHCOAr + RNH-A — > I ; or fi 3*

(d) the compounds of Equation 4 in an inert solvent at 20° to

80°C for 0.5 to 24 hours and in the presence of 1 to 1.4 equivalents of a base

O II

J-S0 ₂ NH ₂ + ArOCNRA — > I .

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The sulfonylureas of Formula I can be prepared by a number of methods. These methods are described below along with the appropriate references for greater detail.

Equation 1

J-S0 ₂ NCO + R-NH-A — > I W W

One of the methods of synthesis of sulfonylureas of Formula I is depicted in Equation 1 where J, R, and A are as defined above. A sulfonyHsocyanate of Formula . is contacted with a heterocyclic amine of Formula & in an inert polar aprotic solvent, such as acetonitrile, dichloromethane, etc. for periods of several minutes to 24 hours or more, preferably at a temperature in the range of 20° to 80°C to afford a sulfonylurea of Formula I.

U.S. Patents Nos. 4,127,405; 4,257,802; and 4,221,585 disclose this equation and are herein incorporated by reference. Equation 2

O

II

J-S0 ₂ NH ₂ + R ⁶⁸ OCNR-A 4 £

Another method of synthesis of compounds of Formula I is depicted in Equation 2 where J, R, and A are as defined previously and R" ⁸ is lower alkyl such as methyl or ethyl. A sulfonamide of Formula 4 is contacted with an alkyl carbamate of Formula 5 n the presence of a trialkylaluminum in an inert solvent such as dichloromethane, 1,2- dichloroethane, etc., and subsequently treated with aqueous acid to afford a sulfonylurea of Formula I. This reaction is taught in European Patent Publication EP-A-83,975 (published July, 20 1983).

Equation 3

O

II J-S0 ₂ NHCOAr + RNH-A — > I £ a

Alternatively, compounds of Formula I can be prepared by the method shown in Equation 3 where A, J, and R are as defined previously and Ar represents an aryl group, for example a phenyl group. In this reaction, a sulfonylcarbamate of Formula fi is contacted with a heterocycHc amine of Formula 3. in an inert solvent such as j>-dioxane for a period of 0.5 to 24 hours, as taught in European Patent PubHcation EP- A-44,807.

Equation 4

A fourth method of preparation for compounds of Formula I is depicted in Equation 4 where A, R, and J are as defined previously and Ar represents an aryl group, for example a phenyl or substituted phenyl group. In this reaction, a sulfonamide of Formula is contacted with a heterocycHc carbamate of Formula 7 in an inert solvent such as p.-dioxane or acetonitrile preferably at temperatures in the range of from 20° to 80°C for periods of 0.5 to 24 hours in the presence of 1 to 1.4 equivalents of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resultant products are isolated by dilution of the reaction mixture with aqueous acid to afford sulfonylureas of Formula I. The reaction is taught in European Patent Publications EP-A-44,807, and EP-A-85,028.

Intermediate Compounds

HeterocycHc sulfonyl isocyanates of Formula _ can be prepared by treatment of sulfonamides of Formula 4 by the procedures taught in U.S. 4,127,405. Heterocyclic carbamates of Formula f> are prepared by procedures taught in European Patent PubHcation EP-A-83,975. The sulfbnylcarbamates of Formula £ and heterocycHc carbamates of Formula 2 can be prepared by procedures taught in European Patent Pubhcations EP-A-44,807, EP-A-72,347, EP-A-173,498 and U.S. Patent 4,666,506 and references cited therein.

The intermediate pyrrole sulfonamides of Formula 4 can be prepared by a variety of methods, some of which are described in the sequence of reactions shown in Equations 5 through 24.

The sulfonamides of Formula 4 of this invention where J is J-l, J-2 or J-3 as defined above can be synthesized from the precursor sulfonamides of Formula fi where J is as defined above and R^ ⁹ is a suitable protecting group such as tert-alkyl or trialkylsilyl, by appropriate methods known to one skilled in the art, as depicted in Equation 5.

Equation 5

acid

£ 4

Sulfonamides of Formula 8_ where J is J-2 or J-3, is as defined above or is a masked synthon thereof, R ² is as defined above or is a masked synthon thereof, R*> ⁹ is as previously defined and R ⁴ is other than H, X^ is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, may be prepared by methods similar to the depiction in Equation 6. The general methodology described for the instance when J is J-2 is directly applicable to the instances where J is J-3. Further, the synthetic necessity, and selection of specific masked

synthons for specific definitions of R and R ² are known to one skilled in the art, for the introduction of R ⁴ into the sulfonamide of Formula £. Equation 6

A sulfonamide of Formula £ can be metalated on carbon using an excess of an organometalHc base, preferably an organoHthium reagent such as ji-butylHthium, a-butyUithium/tetranιethylethylenedianιine (TMEDA) or Hthium diisopropylamide in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100° to -70°C, foUowed by quenching with the appropriate electrophiHc reagent (R ⁴ -X*>) affording sulfonamide of Formula _£ after standard aqueous workup. A sulfonamide of Formula £ where J is J-2, R*, R ² and R^ are as previously defined, ^~ X9 is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, acid chloride or N,N- dialkylamide, can be prepared by methods similar to those depicted in Equation 7.

Equation 7

10. 2

A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometaUic base, as described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc. Perkin Trans.. I, p. 1343, (1982) and the references cited therein, preferably an organoHthium reagent such as n-butylHthium, n-butyllithium/ tetramethylethylenediamine (TMEDA) or Hthium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100° to -70°C, followed by quenching with an appropriate electrophihc reagent (R -X°) affording sulfonamide of Formula fi after standard aqueous workup. A sulfonamide of Formula £ where J is J-3, R , R ² and > ⁹ are as previously defined, X is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, can be prepared by methods similar to those depicted in Equation 8. Equation 8

11

A sulfonamide of Formula H can be treated with a base such as an alkaH metal alkoxide, hydride or tertiary amine and an appropriate electrophiHc reagent (Rl-X^) as shown in an inert solvent, preferably a polar aprotic solvent such as dimethylforπiamide (DMF) to afford a sulfonamide of Formula £. Sulfonamides of Formula 1£, where J is J-2, Rl, R^ ⁹ and X> are as previously defined, can be prepared by methods similar to those depicted in Equation 9. Equation 9

¹² lfl

A sulfonamide of Formula 12 is treated with a base such as an alkali metal alkoxide, hydride or tertiary amine and an appropriate electrophiHc reagent (Rl-χ5) as shown in an inert solvent, preferably a polar aprotic solvent such as dimethylformamide (DMF), at a temperature in the range of 20° to 80°C, for a period of 1 to 24 hours to afford a sulfonamide of Formula 10.

Pyrrole sulfonamides of Formula 12, where R^ is a suitable protecting group as defined above are available from the corresponding bromopyrroles 12. as outHned in Equation 10, where ™ is lower alkyl, such as isopropyl.

N-Silyl-protected pyrrole IS where R™ is preferably an isopropyl group, is treated with an alkylHthium reagent such as fi-butylHthium as described in Chem. Ber.. Vol 122 p.169 (1989), and references cited therein. The resultant metalated species is treated with sulfur dioxide to afford stilfinate salt 14 which can be converted to sulfonamide 2 . by any of several known methods, for example treatment with N- chlorosucciiiimide followed by amination with an appropriate primary amine as disclosed in U.S. Patent 4,481,029. The N-silyl group is then removed, most conveniently with an alkaH fluoride or quaternary ammonium fluoride salt to afford pyrrole-3-sulfonamide 12.

Sulfonamides of Formula H, where J is J-3, R ² , R^ ⁹ and X^ are as previously defined, can be prepared by methods similar to those depicted in Equation 11, where R™ is lower alkyl, such as isopropyl. Equation 11

IS 12 11

A sulfonamide of Formula IS undergoes metal-halogen exchange on carbon using an excess of organometaUic base, as described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc. Perkin Trans.. I, p. 1343, (1982) and the references cited therein, preferably an organoHthium reagent such as B-butyUithium, β-butyl- Hthium/tetrainethylethylenediamine (TMEDA) in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100° to -70°C, foUowed by quenching with an appropriate electrophiHc reagent (R ² -X°) affording intermediate sulfonamide of Formula 12- The N-silyl group is then removed, most conveniently with an alkali fluoride or quaternary ammonium fluoride salt to afford sulfonamide H.

A pyrrole sulfonamide of Formula i >, where R^ ⁹ is a suitable protecting group as defined above can be prepared from the corresponding bromopyrrole 12. as outHned in Equation 12, where R ⁷ ^ is lower alkyl, such as isopropyl. Equation 12

12 lfi ιa lfi

N-silyl-protected pyrrole 12. where R ⁷ ^ is preferably an isopropyl group, is treated with an alkylHthium reagent such as n.-butylHthium as described in Chem. Ber.. Vol. 122, p. 169 (1989), and references cited therein. The resultant metalated species is treated with sulfur dioxide to afford sulfinate salt Jj£ which can be converted to sulfonamide 1£ by any of several known methods, for example treatment with N-chloro- succinimide in a solvent such as acetic acid, methylene chloride/H2θ,

l,l,2-trichlorotrifluoroethene/H2θ at a temperature from 0°C to ambient temperature foUowed by amination with an appropriate primary amine as disclosed in U.S. Patent 4,481,029. Sulfonamide 1£ can be converted to a compound of Formula 23. by treatment with N-bromosuccinimide in an inert solvent such as tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100 to -70°C as described in J. Org. Chem.. Vol. 55, No. 26, pp. 637-28 (1990) and the references cited therein.

In the cases where R ² is not directly obtainable as an electrophiHc reagent (R ² -X ⁵ ), wherein R ² is defined as -S(0)2NR1 ⁸ 1 ⁹ , -CONRIORH, C(R ¹² )=NOR ¹³ , -S(0) _n -Rl ⁷ , C(0)R ⁸ , (CH ₂ ) _m -Q ² or "CN the desired compounds can be obtained through a series of functional group transformations known to one skilled in the art. The general methodology described for the instance when J is J-2 is directly appHcable to the instances where J is J-l or J-3 with modifications known to one skilled in the art. Therefore, only the instances where J is J-2, Rl is CH3 and R^ ⁹ is a suitable protecting group such as tert-alkyl or trialkylsilyl will be described in Equations 13 to 19.

Equation 13 depicts a sequence of reactions whereby one can obtain a sulfonamide of Formula 21 where J is J-2, Rl and R^ ⁹ are as previously defined and R ² is -S(0)2NR1 ⁸ R ⁹ wherein Rl ⁸ and Rl ⁹ are as defined above. Equation 13

lfi 2fi 21

A precursor sulfonamide of Formula 1_Q_ can be metalated on carbon using an excess of organometaUic base, similar to that described in _J

Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc- Pprkin Trans.. I, p. 1343, (1982) and the references cited therein, preferably an organoHthium reagent such as a-butyUithium, a-butylHthium/tetra- methylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100° to -70°C. The resultant metalated species is treated with sulfur dioxide to afford sulfinate salt 20. which can be converted to sulfonamide 21 by any of several known methods, for example treatment with N-cMorosuccimmide foUowed by amination with an appropriate amine in an analogous manner to that disclosed in U.S. Patent 4,481,029.

In an analogous manner Equation 14 outlines a sequence wherein one can prepare a sulfonamide of Formula 22 where J is J-2, Rl and R^ are as previously defined and R ² is -C(O)NR10R11. Equation 14

A precursor sulfonamide of Formula £ where R ² is defined for example as -C(0)OR ⁹ where R ⁹ is preferably methyl or ethyl, can be converted to amide 22 by any of several known methods, for example contacting the ester with an appropriate amine in the presence of an organometaUic base in an analogous manner to that disclosed in Tetrahedron Letters. No. 21, p. 1791, (1970). Equation 15 outHnes a sequence whereby one can prepare a sulfonamide of Formula 23 where J is J-2, Rl and R^ ⁹ are as previously defined and R ² is -CN.

Equation 15

A precursor sulfonamide of Formula £ where R ² is defined for example as -CONH2 can be converted to nitrile 22. by any of several known methods, for example contacting the amide with triphenylphosphine and CCI4 in an inert solvent, in an analogous manner to that disclosed in Tetrahedron Letters. No. 21, p. 4383, (1970), or by dehydration with thionyl chloride as described in Org. Syn.. coll. vol. r , p. 436, (1963).

Equation 16 depicts a sequence whereby one can prepare a sulfonamide of Formula 25 where J is J-2, Rl and R*> ⁹ are as previously defined, R ² is (CH ₂ ) _m -Q ² , Q ² is Q ² -l, Q ² -4, Q ² -5, Q ² -6, Q ² -7, Q ² -8, Q ² - 9, Q ² -10 or Q ² -ll, r is 0, m is 0 and M is ZnCl _x , ZnBr _x , or B(OH)2- Equation 16

lfl 24 25

A sulfonamide of Formula IQ can be metalated on carbon using an excess of organometaUic base, similar to that described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc- pr in T pns-, I, p. 1343, (1982) and the references cited therein, preferably an organolithium

reagent such as a-butyUithium, fl-butylHthium/tetramethylethylene- diamine (TMEDA) or Hthium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of - 100° to -70°C. The metalated species can be transmetalated with anhydrous zinc chloride, by methods similar to those described in Tetrahedron Letters. Vol.29, No.39, pp. 5013-5016, (1988). The transmetalated species 24 can be coupled to an arylhaHde substrate, for instance 2-bromopyridine, in the presence of excess zinc chloride and a palladium catalyst to afford the biaryl species of Formula 25. Alternatively, the metalated species can be quenched with an alkyl borate, for instance trimethylborate affording the corresponding 2-boronic acid species 24 upon hydrolysis. The pyrrole boronic acid species can be coupled to an arylhaHde substrate by methods similar to those described in Tetrahedron Letters, vol. 26, No. 49, pp. 5997-6000, (1985) and Tetrahedron Letters, vol. 29, No. 43, p. 5459-5462, (1988) and the references cited therein, for instance 2-bromopyridine in the presence of a paUadium catalyst and a base, in an inert solvent such as toluene or dimethoxyethane (DME), at reflux temperature for periods of 1 to 24 hours affording the biaryl species of Formula 25.

Equation 17 outlines a sequence whereby one can prepare a sulfonamide of Formula 22 where J is J-2, Rl and R^ are as previously defined, R ² is -C(Rl ² )=NORl ³ , R ⁱ² is H and R ⁱ³ is as previously defined. Equation 17

SOoNHR ⁶⁹

in 2£ 22

A sulfonamide of Formula 1Q can be metalated on carbon using an excess of organometaUic base, similar to that described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc. Parkin Trans.. I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as a-butylHthium, a-butyUithium/tetramethylethylene- diamine (TMEDA) or Hthium dusopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of - 100° to -70°C. The metalated species, quenched with dimethylformamide (DMF) affords the corresponding pyrrole-2-aldehyde 2fi following aqueous workup. The aldehyde species 26. is contacted with an alkoxy amine

(H2N-OR ³ ), for instance methoxylamine hydrochloride in the presence of a base, for example sodium acetate, in an inert solvent such as acetone, tetrahydrofuran, dioxane or methanol. The reaction is carried out at temperatures in the range of 20°C to reflux for a period of 1 to 24 hours and optionally in the presence of a phase transfer catalyst such as a crown ether.

Equation 18 depicts a sequence whereby one can prepare a sulfonamide of Formula 2£ where J is J-2, Rl and R^ ⁹ are as previously defined and R ² is -C(0)R ⁸ where R ⁸ is as defined above. Equation 18

lfi 22 22

A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometaUic base, similar to that described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc. Perkin Trans.. I, p. 1343,

(1982) and the references cited therein, preferably an organoHthium reagent such as a-butyUithium, n-butyUithium/tetramethyl- ethylenediamine (TMEDA) or Hthium dusopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100° to -70°C. The metalated species, quenched with an aldehyde (R ⁸ -CHO) affords the alcohol 2£ foUowing aqueous workup. Alcohol 2£ can be oxidized to a ketone of Formula 2£ by contact with one of several oxidants known to one skilled in the art, for example tetra-n-propylammonium perruthenate/ N-methylmorpholine N-oxide as described in Aldriς.foimica Acta. Vol. 23, No. 1, p. 13-17, (1990) and the references cited therein.

Equation 19 outlines a sequence whereby one can prepare a sulfonamide of Formula 21 where J is J-2, Rl and R^ ⁹ are as previously defined and R ² is -S(0) _n -R , where Rl ⁷ is as defined above and n is 1 or 2.

Equation 19

ifi 22 21

A sulfonamide of Formula 1£ can be metalated on carbon using an excess of organometaUic base, similar to that described in J. Org. Chem.. vol. 50, p. 4362-4368, (1985) and J. Chem Soc. Perkin Trans.. I, p. 1343, (1982) and the references cited therein, preferably an organoHthium reagent such as n-butylHthium, n-butyUithium/tetramethyl- ethylenediamine (TMEDA) or Hthium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a

temperature in the range of -100° to -70°C. The metalated species, quenched with an appropriate disulfide (R1 ⁷ -S-S-R1 ⁷ ) affords thioether 30 foUowing aqueous workup. The thioether can be oxidized selectively to the corresponding sulfoxide or sulfone of Formula .21 by contact with one of several suitable oxidants such as a peroxy acid or hydrogen peroxide.

Pyrrole sulfonamide precursors of Formula 2fi where J is J-l, R ³ is H or alkyl and R^ ⁹ is a trialkylsilyl protecting group can be prepared from the corresponding N-substituted pyrrole 22 as outHned in Equation 20. Equation 20

22 22. 24

4 22 22

Pyrroles of Formula 22 are generaUy known in the art or can be prepared by a variety of known alkylation or acylation procedures such as those reviewed in "Pyrroles", R. Alan Jones, Ed., "The Chemistry of HeterocycHc Compounds", Vol. 48, Part 1 (John Wiley & Sons, Inc., 1990, New York) p. 397. Metalation of pyrroles 22 is likewise known to produce reactive 2-lithio intermediates as described in Synthetic r.oτnmnn rat. nn _H Vol. 12, p. 231 (1982) and in J. Org. Chem.. Vol. 46, p. 157 (1981) and references cited therein. Treatment of these reactive

metalated species with sulfur dioxide affords sulfinate salts 22- These can be converted to sulfonamides 34 by methods described above, or directly by treatment with hydroxylamine-O-sulfonic acid in aqueous media as described in Synthesis, p. 1031 (1986). Treatment of sulfonamides 24 with a base and a trialkylsilyl chloride such as t- butyldimethylsUyl chloride affords the protected sulfonamides 35.

Metalation of 5 with two equivalents of an organometaUic base such as n-butylHthium, Hthium dusopropylamide or Hthium 2,2,6,6- tetramethylpiperidide (LTMP) and quenching with an appropriate electrophiHc reagent R χ5 affords substituted sulfonamides 36. Directed metalations of this type on 1,2-disubstituted pyrroles have been described in J. Org. Chem.. Vol. 50, p. 4362 (1985) and J. Chem. Soc Pa Trans. I, p. 1343 (1982) and references cited therein. When 22 contains Rl groups that are incompatible with strongly basic conditions of the subsequent reactions, such as when R is CO2CH3 or C(0)CH3, a suitable protecting group in place of Rl can be substituted such as those described in J. Org. Chem.. Vol 46, p. 157 (1981), ibid., p. 3760, and in Vol. 42, p. 3723 (1986). This protecting group can be removed at a suitable point in the synthesis, such as after the synthesis of sulfonamide 2fi, and replaced with the appropriate Rl group by standard alkylation or acylation methods as described above.

Intermediates 24 or 25 where R ³ is hydrogen can be directly halogenated to afford the corresponding substituted sulfonamides 24 or 25 where R ³ is halogen. Conversion of these intermediates to sulfonamides of Formula 36 where R ³ is halogen is best carried out using a substituted Hthium amide base, such as Hthium dusopropylamide, foUowed by treatment with an electrophilHc reagent as described above.

Intermediate sulfonamides of Formula 22 where J is J-l and R ⁷ 1 is other than H can be prepared as depicted in Equation 21 from the corresponding sulfonamides 2_6_, where X" is chloro, bromo or iodo.

Equation 21

⁹

2& 22 afi

Treatment of sulfonamides 20. with a halogenating agent affords sulfonamides 22 where X ⁸ is chloro, bromo, or iodo. Further treatment of 37 where X ⁸ is bromo or iodo with an alkylHthium in an inert solvent followed by an alkyl hahde affords sulfonamides 22 where R ⁷ is lower alkyl. Likewise treatment of 22 with an alkylHthium reagent and subsequently with a mild fluorinating agent such as that described in _J Am. Chem. Soc. Vol. 106, p. 452 (1984) affords sulfonamides 22 wherein R is a fluoro substituent. Compounds of 22 where X ⁸ is bromo or iodo to 3_S where R ⁷ 1 is CF3 can be accomplished by first treatment with an alkylHthium reagent foUowed by quenching with carbon dioxide to afford an intermediate acid 22 where R ⁷ 1 is COOH, and subsequent reaction with sulfur tetrafluoride or the like.

An intermediate pyrrole of Formula 4Q where Rl is defined as Ql above, can be prepared by the method outlined in Equation 22. Equation 22

22 42

Amine 2£ can be condensed with 2,5-dimethoxy tetrahydrofuran by the method described in Org. Svn.. coll. vol. V, pp. 716-717, affording pyrrole 4Q-

Intermediate sulfonamides of Formula 44 where J is J-l, R ³ is H, is Q and R ⁸⁹ is a trialkylsUyl protective group can be prepared from the corresponding N-substituted pyrrole 4£ as depicted in Equation 23. Equation 23

1) n-Buϋ

^ 41 42

? SO — ₂ NH ₂ 9

42 42 44

Pyrroles of Formula 4£ can be metalated on carbon using an organometaUic base, as described in Org. React., vol. 26, p. 21 (1979) and the references cited therein, preferably using an organoHthium reagent such as n-butyUithium, Hthium diisopropyl amide, or n- butyUithium/tetrainethylethylenediamine. Treatment of the metalated species with sulfur dioxide affords the sulfinate salts 41. These can be converted to sulfonamides 42 by methods described above. Treatment of 42 with a base and a trialkylsU l chloride affords protected sulfonamides 43. Metalation of 42 with two equivalents of an organometalHc base as described above, and quenching with an appropriate electrophiHc reagent χ5 affords substituted sulfonamides 44. Intermediate sulfonamides of Formula 4£ where J is J-2, R ⁴ is H,

Rl is Ql and R ⁸⁹ is a trialkylsUyl protecting group can be prepared from the corresponding N-substituted pyrrole Q as outHned in Equation 24.

Equation 24

S0 ₂ NH ₂

42 45 42 42

42 42 42

Pyrroles of Formula 4Q can be brominated by methods similar to those reviewed in "Pyrroles," R. Alan Jones, Ed., "The Chemistry of HeterocycHc Compounds," vol. 48, Prt. 1 (John Wiley & Sons, Inc., 1990, New York) p. 372, affording 3-bromo pyrroles of Formula 45- Pyrroles of Formula 45 can undergo metal halogen exchange by the methods described above with an organometaUic base, preferably an organoHthium reagent. Treatment of the metalated species with sulfur dioxide affords sulfinite salts 4£. These salts can be converted to sulfonamides 42 by methods described above. Treatment of 4 with a base and a trialkylsUyl chloride affords protected sulfonamides 48.

Metalation of 4S with two equivalents of an organometaUic base such as n-butyUithium, lithium diisopropyl amide or n-butyllithium/tetramethyl- ethylenediamine and quenching with an appropriate electrophiHc reagent R ² χ5 affords substituted sulfonamides 4£ Directed metalation of 1,3- disubstituted pyrroles is described above.

Compounds of Formula 52 can be prepared by the method outHned in Equation 25.

Equation 25

Compound 5£, prepared by the method described in J. Org. Chem.. 55, 6317 (1990), is treated with 1 equivalent of an alkylHthium reagent such as n-butyUithium, and the resulting metalated species is treated with sulfur dioxide to obtain sulfinate salt 51 which can be converted to sulfonamide 52 by any of several known methods. For example treatment with N-cMorosuccinimide in acetic acid, foUowed by amination. The sulfonamide 52 is treated with a base such as an alkaU metal alkoxide, hydride or tertiary amine and an appropriate ele ϊrophilic reagent (R -X ⁵ ) as shown in an inert solvent, to give a sulfonamide of Formula 53.

Sulfonamides of Formula 54 or 55 can be prepared by methods similar to those depicted in Equation 26. Equation 26

54

55

Sulfonamide 52 can be treated with cupric cyanide in a polar aprotic solvent preferably DMF, at a temperature in the range of 100° to 155°C. For a period of 6 to 28 hours to afford a sulfonamide of Formula 54- Treatment of sulfonamide 52 with an aryl boronic acid in the presence of a palladium (O) catalyst, such as tetrakis (triphenylphosphine) palladium, and an inorganic base, such as sodium carbonate, by methods similar to those described in Synthetic Comm.. 11 513 (1981), affords sulfonamides of Formula 55. Sulfonamides of Formula H may also be prepared by the method depicted in Equation 27. Equation 27

56 ⁵⁷ 11

N-SUyl-protected pyrrole Ω where i _s preferably an isopropyl group, is treated with an alkylHthium reagent such as n-butyUithium, and the resulting metalated species is treated with an appropriate electrophiHc reagent (R ² -X^) as shown in an inert solvent to afford compound 5fi. Similar treatment of compound 5S with an alkylHthium reagent such as n-butyUithium and quenching of the metalated species thus formed with sulfur dioxide affords the sulfinate salt 52 which can be

converted to sulfonamide 11 by any of several known methods as described above.

The synthesis of heterocyclic amine derivatives such as those depicted in Formulas _> 5 and 2 are either known, or can be prepared by obvious methods known to one skiUed in the art. For a review of the synthesis and reactions of 2-amino- and 2-methylam opyrimidines see The _' h ^p mistry of Heterocycli CQmpQtøη«fø _r vol 16, Wiley-Inter science, New York (1962). For a review of the synthesis and reactions of 2-amino- and 2-methylamino-s-triazines, see ? Ch mistry of HeterocycHc Compoun ;^ vol 13, WUey-Interscience, New York (1959), F.C. Schaefer U.S. Patent 3,154,537 and F.C. Schaefer and KR. Huffman J. Org.

Chem.. 28, 1812 (1963). J. Chem. Soc. 2031 (1966), EP-A-173,498 and U.S. Patent No. 4,666,506 describes further methods. The synthesis of the bicyclic amines of Formula 2 where A is A-2 and A-3 is taught in U.S. Patent No. 4,339,267. The synthesis of bicycHc amines of Formula 2, where A is A-4 is taught in European Patent PubHcation EP-A-46,667. The synthesis of compounds of Formula 2 where A is A-5 are described European Patent Publication EP-A-73,562. The synthesis of compounds of Formula 2 where A is A-6 are described European Patent PubHcation EP-A-94,260. The compounds of Formula 2 where A is A-7 can be prepared by methods taught in EP-A-125,864 (pubhshed 11/21/84) or by suitable modifications that would be obvious to one skiUed in the art.

The amines of Formula A where χl is OCF2H can be prepared by methods taught in EP-A-72,347, or by suitable modifications that would be obvious to one skilled in the art.

The pyrimidines of Formula 2 where A is A-l (Z=CH) and where Y is

can be prepared according to the method taught in European Patent Publication EP-A-84,224 or suitable modifications thereof known to one skiUed in the art.

Agricultural suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkaH or alkaUne earth metal salt having a sufficiently basic anion ( e.g., hydroxide, alkoxide, carbonate or hydroxides). Quaternary amine salts can be made by similar techniques. Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., potassium, sodium or calcium salt.

Acid addition salts useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., o- toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further iUustrated by the following specific examples. Abbreviations for nuclear magnetic resonance (NMR) signals are: s = singlet, bs = broad singlet, d = doublet, t = triplet, m = multiplet, q = quartet, and peak positions are reported as parts per million downfield from internal tetramethylsUane. Infrared (IR) peak positions are given in reciprocal centimeters (cm"l) and sh denotes shoulder.

N-(l.l-Dimethylethyl)-l-rtris(l-methylethyl)sUyll- lH-3-sulfonamide A solution of 30.25 g (0.10 mol) of 3-bromo-N-triisopropyl- sUylpyrrole in 500 mL of anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -78°C. The colorless solution was treated with 44 mL of 2.38 M n-butyUithium in hexanes (0.105 mol) dropwise at such a rate as to keep the temperature below -65°C. After ca. 1 hour at -78°C, Hquified sulfur dioxide was added (25.8 ml, 0.6 mol). The amber solution was warmed to room temperature and stirred for ca. 1 hour. The THF was removed under reduced pressure. The resulting amber oU was dissolved in 500 mL glacial acetic acid, cooled to 20°C and then treated with 13.35 g (0.1 mol) of N-cMorosuccinimide. After ca. 1 hour at room temperature the acetic acid was evaporated at reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed successively with water, NaHC03 solution, brine, then dried

(MgSθ4) and evaporated ia vacuo. The resulting amber oU residue was dissolved in methylene chloride 500 mL cooled to -20°C and treated with t-butylamine. The resulting dark brown turbid solution was aUowed to warm to room temperature and stir overnight ca. 16 hours. The solution was washed with IN HCl, dried (MgS04) and evaporated to a dark oU.

Chromatography on siHca gel (20% ethyl acetate/80% hexanes) afforded 10.48 g of the title compound as a cream colored soHd, m.p. 103-104°C. iH NMR (CDC1 ₃ , 200 MHz.) δ : 7.28 (d,lH), 6.74(m,lH), 6.56(bs,lH),

4.39(bs,lH), 1.45(m,3H), 1.23(s,9H), 1.08(d,18H). Example 2

N-( 1. l-Dimethylethyl)-lH-pyrrole-3-su)fon a mi d P A solution of N-(l,l-dimethylethyl)-l-[tris-(l-methylethyl)silyl]- lH-3-sulfonamide (10.48 g, 0.0293 mol) in 100 mL diethyl ether under a nitrogen atmosphere was treated with tetrabutylammoniumfluoride- hydrate 10.16 g (0.0388 mol) followed by 1.8 mL of glacial acetic acid. After stirring ca. 1.5 hours at room temperature, the reaction mixture was filtered through siHca with diethyl ether rinse. The filtrate was

concentrated ia vaςuo affording 4.1 g of the title compound as a white solid, m.p. 146-148°C. iH NMR (CDC1 ₃ , 200 MHz.) δ : 8.58(bs,lH), 7.32(s,lH), 6.79(d,lH),

6.52(d,lH), 4.34(bs,lH), 1.26(s,9H).

N-(l.l-Dimethylethyl)-l-methyl-lH-pyrrole-3-sulfonf mif| ^p

A solution of N-(l,l-dimethylethyl)-lH-pyrrole-3-sulfonamide 9 g (0.044 mol) in 90 mT ^, N,N-dimethylforamide was cooled to 15°C under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide foUowed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60°C for 2 hours then aUowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was dUuted with ethyl acetate, washed three times with IN HCl, once with brine, dried (MgSθ4) and evaporated to an oily soHd which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, mp. 134-135°C. lH NMR (CDCI3, 200 MHz.) δ: 7.11(s,lH), 6.59(d,lH), 6.41(d,lH),

4.32(bs,lH), 3.67(s,3H), 1.26(s,9H).

Eftλmple 4 Methvl 3-rr(l . ^ ^ p byl^ D Tn olsulfonvn-l- methvl-lH-pvrrole-2-carboxvlate

To a solution of 1 g (4.62 mmol) of N-(l,l-dimethylethyl)-l-methyl- lH-pyrrole-3-sulfonamide in 150 mL THF under a nitrogen atmosphere cooled to -78°C was added dropwise at such a rate as to keep the temperature below -65°C 4.1 mL (9.48 mmol) 2.32 M n-butylHthium in hexanes. The resulting amber turbid solution was stirred at -78°C for ca. 30 minutes. Methyl chloroformate (0.37 mL, 4.86 mmol) was added in one portion and the resulting gold reaction mixture was allowed to warm to room temperature and stirred for ca. 1.5 hours. The gold reaction mixture was cooled to 0°C and acidified with IN HCl. The THF phase was separated washed with brine, dried (MgS04) and concentrated to an amber oil. The NMR of the crude reaction product was consistent with the title compound, additionally the NMR indicated that a trace of the

starting material was also present. The crude material was combined with the product from a similar reaction run on the scale described below and chromatographed to give the title compound.

To a solution of 5 g (23 mmol) of N-(l,l-dimethylethyl)-l-methyl- lH-pyrrole-3-sulfonamide in 150 mT ^, THF under nitrogen atmosphere cooled to -78°C was added dropwise, at such a rate as to keep the temperature below -65°C, 20 mL (47.4 mmol) 2.32 M n-butyUithium in hexanes. The resulting amber turbid solution was stirred at -78°C for ca. 30 minutes. 1.87 mL (24.3 mmol) of methyl chlorofoπnate was add in one portion and the resulting gold reaction mixture was aUowed to warm to room temperature and stir for ca. 1.5 hours. The gold reaction mixture was cooled to 0°C and acidified with IN HCl. The THF phase was separated, washed with brine, dried (MgS04) and concentrated to an amber oU. The oil was combined with the crude product from the previous example and chromatographed on silica (30% ethyl acetate/70% hexanes) affording 3.53 g of the title compound as a solid.

!H NMR (CDCI3, 200 MHz.) δ: 6.71(dd,2H), 5.72(bs,lH), 3.95(s,3H),

3.91(s,3H), 1.24(s,9H).

F,τaτnp1p Ft

Methyl 3-(aminosuuOnv -l-methyl-lH-pyrrole-2-carboxylate To a solution of 3.53 g of methyl 3-[[(l,l-dimethylethyl)amino]- sxιlfonyl]-l-methyl-lH-pyrrole-2-carboxylate in 40 mL of methylene chloride under an nitrogen atmosphere was added 80 mL of trifluoroacetic acid (TFA). The gold solution was stirred at room temperature overnight ca. 16 hours. The gold solution was concentrated to an oily residue. Diethyl ether was added to the residue and removed by evaporation to remove residual TFA. The resulting soHd was suspended in diethyl ether and filtered affording the title compound as a tan soHd, m.p. 105-107°C. iH NMR (Acetone-d ₆ , 200 MHz.) δ: 7.01(d,lH), 6.51(d,lH), 6.28(bs,2H), 3.95(s,3H), 3.93(s,3H).

Methyl 3-rrrr 4.6^di™gthoxy-2-pyrimiflny )- ^flm ,i ⁿ olCffrbonvllamino1sulfonvl-l-methvl-lH-pyrrole-2-carbo xvlate 0.22 g (1 mmol) of methyl 3-(aminosulfonyl)-l-naethyl-lH-pyrrole- 2-carboxylate and 0.28 g (1 mmol) of phenyl (4,6-dimethoxy-2-pyrimi- dinyl) carbamate were combined in 4 mL of acetonitrile, 0.2 mL (1.33 mmol) of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added and the resulting amber reaction mixture was aUowed to stand at room temperature overnight ca. 16 hours. The reaction mixture was diluted with 6 mT, of water and ca. 2 mL of shaved ice, acidified with cone HCl (ca. 8 drops) to pH 4. The resulting precipitate was filtered washed with water followed by diethyl ether and air dried affording 0.2 g of the title compound as a soHd m.p. 182.5-186.5°C. H NMR (Me2SO-de, 200 MHz.) δ: 12.45(bs,lH), 10.45(bs,lH),

7.21(d,lH), 6.65(d,lH), 6.01(s,lH), 3.93(s,6H), 3.85(s,3H), 3.7(s,3H). Example 7

N-(l.l-Dimethylethyl)-l-methyl-2-

(methylthio)-lH-pyrrole-3-sulfnnami^

To a solution of 6.48 g (30 mmol) of N-(l,l-dimethylethyl)-l- methyl-lH-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78°C was added dropwise at such a rate as to keep the temperature below -65°C 25.52 mL (61.5 mmol) 2.41 M n- butylHthium in hexanes. The reaction was stirred at -78°C for ca. 30 minutes. To the reaction mixture was added 2.97 mL (33 mmol) of dimethyldisulfide in one portion and the resulting reaction mixture was aUowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to 0°C and acidified with IN HCl. The THF phase was separated washed with brine, dried (MgSθ4) and concentrated iS vacuo. The crude residue was chromatographed on siHca (20% ethyl acetate/80% hexanes) affording 4.63 g of the title compound as an off white soHd, m.p. 116-119°C. iH NMR (CDCI3, 200 MHz.) δ: 6.72(d,lH), 6.58(d,lH), 4.96(bs,lH),

3.74(s,3H), 2.35(s,3H), 1.23(s,9H).

l-Methvl-2-(methvlthio)-lH-pvrro1p-a-p ι1fπη^mi^P

To a solution of 4.63 g (17.66 mmol) N-(l,l-dimethylethyl)-l- methyl-2-(methylthio)-lH-pyrrole-3-sulfonamide in 50 L of methylene chloride was added 50 mL of trifluoroacetic acid (TFA) under a nitrogen atmosphere. The orange reaction mixture was stirred at room temperature overnight ca. 16 hours. The reaction mixture was concentrated to a tan soHd. Diethyl ether was added to the tan soHd and was removed by evaporation to remove residual TFA. The soHd was suspended in diethyl ether and filtered giving 2.9 g of the title compound as a soHd, m.p. 135-137°C.

1H NMR (Acetone-d ₆ , 200 MHz.) δ: 6.93(d,lH), 6.45(d,lH), 6.19(bs,2H),

3.78(s,3H), 2.33(s,3H).

E-gflm Ip

2-Bromo-N-(l.l-dimethvIethyl)- l-methyl-lH-pyrrole-3-sulfon ami d p

To a solution of 8.85 g (41 mmol) of N-(l,l-dimethylethyl)-l- methyl-lH-pyrrole-3-sulfonamide in 200 mT. diethyl ether under a nitrogen atmosphere cooled to -78°C was added dropwise, at such a rate as to keep the temperature below -65°C, 36.0 mL (85 mmol) 2.41 M n- butyUithium in hexanes. The reaction was stirred at -78°C for ca. 15 minutes. To the reaction mixture was added 2.2 mL (41 mmol) of bromine dropwise. The Hght orange reaction mixture was aUowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture darkened as it stirred at room temperature. The reaction mixture was cooled to 0°C and acidified with IN HCl. The ether phase was separated, washed with brine, dried (MgS04) and concentrated in vacuo. The crude residue was chromatographed on siHca (25% ethyl acetate/80% hexanes) affording 7.11 g of the title compound as an orange oil. iH NMR (CDCI3, 200 MHz.) δ: 6.73(d,lH), 6.62(d,lH), 3.63(s,3H), 1.24(s,9H).

Example 10

2-Bromo- l-methyl-lH-pyrrole-3-sιι lfon gmi <Je To a solution of 7.11 g (24 mmol) of 2-bromo-N-(l,l-dimethylethyl)- 1 -methyl- lH-pyrrole-3-suKonamide in 50 mL methylene chloride under a nitrogen atmosphere was added 50 mL of TFA. The reaction mixture was aUowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated ia vacuo. Three portions of diethyl ether were added to the crude residue and was removed by evaporation to remove residual TFA, which yielded 1.23 g of the title compound as a light brown solid. iH NMR (Acetone-d ₆ , 200 MHz.) δ: 7.36(d,lH), 6.49(d,lH), 6.3(bs,2H)

3.68(s,3H).

Example 11

N-Q.l-Dimethylethyl)-2-formyl-l-methyl- lH-pyrrole-3- ^g ιι1fnnpmid ^p To a solution of 12.96 g (60 mmol) of N-(l,l-dimethylethyl)-l- methyl-lH-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78°C was added dropwise, at such a rate as to keep the temperature below -65°C, 52.35 mL (123 mmol) 2.35 M n- butylHthium in hexanes. The reaction was stirred at -78°C for ca. 30 minutes. To the reaction mixture was added 4.64 mL (60 mmol) of N,N- dimethylformamide dropwise. The reaction mixture was aUowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture was cooled to 0°C and acidified with IN HCl. The THF phase was separated, washed with brine, dried (MgS04) and concentrated ia vacuo. The crude residue was chromatographed on siHca (25% ethyl acetate/80% hexanes) affording 5.72 g of the title compound as a white solid, m.p. 101.5-103°C. iH NMR (CDCI3, 200 MHz.) δ: 10.25(s,lH), 6.81(d,lH), 6.6(d,lH),

4.93(bs,lH), 3.98(s,3H), 1.27(s,9H).

Example 12 -f 1 ,1 -Pimt»t.hyl^thyl)-2-r(me oγyiminn ^' )- methyll- lH-pyrrole-3-sn 1 frm ^ mi ήe

To a suspension of 3.91 g (46.8 mmol) of methoxyamine hydrochloride in 60 mT. of methanol was added 3.84 g (46.8 mmol) of sodium acetate. After stirring the white suspension for ca. 15 minutes

5.72 g (23 mmol) of N-(l,l-dimethylethyl)-2-formyl-l-methyl-lH-pyrrole-

3-sulfonamide was added in one portion. The white suspension was heated at a gentle reflux overnight ca. 16 hours. The reaction mixture was cooled to room temperature and poured into 500 mL of water. The aqueous mixture was extracted with four 100 mL portions of methylene chloride. The combined extracts were washed with water, dried (MgSθ4) and concentrated ia vacuo yielding 5.74 g of the title compound as a white soHd, m.p. 99-101°C. H NMR (CDC1 ₃ , 200 MHz.) δ: 8.51(s,lH), 6.66(d,lH), 6.54(d,lH), 4.82(bs,lH), 3.97(s,3H), 3.82(s,3H), 1.24(s,9H).

2-f(M< ^a t n yimino)methyl1-l- methvl-lH-pvrr"^-3-a"1 ""a ^

To a solution of 5.74 g (21.9 mmol) of N-(l,l-dimethylethyl)-2- [(naethoxyim___no)-πιethyl]-lH-pyrrole-3-sulfonamide in 75 mT ^, methylene chloride under a nitrogen atmosphere was add 75 mT. of TFA. The clear orange reaction mixture was aUowed to stir at room temperature overnight ca. 16 hours. The orange reaction mixture was concentrated ia vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 3.49 g of the title compound as a gray soHd, m.p. 120-122°C. H NMR (CDCI3, 200 MHz.) δ: 8.43(s,lH), 6.66(d,lH), 6.54(d,lH), 6.1-

6.7(bs,2H), 3.96(s,3H), 3.79(s,3H).

itornple H

M ³ -(^, Pim9 h le hyl)■N ² i ² - riime hyl- lH-pvrrole-2.3-Hisu1fonamide

A solution of 6.48 g (30 mmol) of N-(l,l-dimethylethyl)-l-methyl- lH-pyrrole-3-sutfonamide in 150 mL of anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -78°C. The colorless reaction was treated with 61.5 mmol of 2.38 M n-butyUithium in hexanes dropwise at such a rate as to keep the temperature below -65°C. After ca.

1 hour at -78°C, Hquified sulfur dioxide was added (180 mmol). The amber solution was warmed to room temperature and stirred for ca. 1 hour. The THF was removed under reduced pressure. The residue was dissolved in 150 mL glacial acetic acid, cooled to 20°C and then treated with 31 mmol of N-chlorosuccinimide. After ca. 1 hour at room temperature the acetic acid was evaporated at reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed successively with water, NaHCθ3 solution, brine, dried (MgSθ4) and evaporated invacuo. The residue was dissolved in methylene chloride

(150 T/), cooled to -20°C and treated with 75 mmol of Hquified dimethylamine. The reaction mixture was aUowed to warm to room temperature and stir overnight ca. 16 hours. The solution was washed with IN HCl, dried (MgS04) and evaporated. The crude material was dissolved in acetonitrile and treated with activated charcoal, filtered and concentrated. The residue was triturated with hexanes/n-butyl chloride to yield 6.95 g of the title compound as a Hght brown soHd, m.p. 98-101°C. iH NMR (CDCI3, 200 MHz.) δ: 6.79(d,lH), 6.69(d,lH), 5.77(bs,lH), 3.89(s,3H), 2.92(s,6H), 1.23(s,9H). ffixλ_mp)e 1 (> N ² .N ² .l-Trimethyl-lH-pyrrole-2.3-diaιι|f"η^mif1p

To a solution of 6.95 g (21 mmol) of N ³ -(l,l-dimethylethyl)- N ,N ,l-trimethyl-lH-pyrrole-2,3-disulfonamide in 75 mL of methylene chloride under a nitrogen atmosphere was added 75 mL of TFA. The reaction mixture was aUowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated ia vacuo. Three portions of

diethyl ether were added to the soHd residue and removed by evaporation to remove residual TFA. The solids were suspended in diethyl ether and filtered to yield 4.52 g of the title compound as a soHd, m.p. 146-148°C. H NMR (Acetone-d ₆ , 200 MHz.) δ: 7.1(d,lH), 6.59(d,lH), 6.28(bs,2H),

3.95(s,3H), 2.93(s,6H). F. am l lfi

N-rrf4-Ethyl-6-methoxy-1.3.5-triazinv1-2-vn _a minn1- carbonyl-N.N.l-trimethyl-2 _f 3- i?"1fo"amid ^p 0.27 g (1 mmol) of N ² ,N ² ,l-trimethyl-lH-pyrrole-2,3-disulfonamide and 0.28 g (1 mmol) of phenyl (4-ethyl-6-methoxy-2-triazinyl) carbamate were combined in 4 mT. of acetonitrile 0.2 mL (1.33 mmol) of 1,8- diazabicyclo[5.4.0]undec-7-ene was added and the resulting amber reaction mixture was aUowed to stand at room temperature overnight ca.

16 hours. The reaction mixture was diluted with 6 mL of water and ca. 2 of shaved ice, and was acidified with cone. HCl. The resulting precipitate was filtered, washed with water foUowed by diethyl ether, and air dried affording 0.19 g of the title compound as a solid, m.p. 159-

160.5°C.

!H NMR (Me ₂ SO-d ₆ , 200 MHz.) δ: 12.52(bs,lH), 11.0(s,lH), 7.27(d,lH),

6.75(d,lH), 3.97(s,3H), 3.85(s,3H), 2:80(s,6H), 2.73(q,2H), 1.25(t,3H). Example 17

3-rr(l.l-DimPt v1 ^p γ^amino1sulfonyll-NJ^.l- t.rimet.hv1-1H- yrrθle-2-cqτh ra^if} ^p To a solution of 6.48 g (30 mmol) of N-(l,l-dimethylethyl)-l- methyl-lH-pyrrole-3 -sulfonamide in 150 mT ^, THF under a nitrogen atmosphere cooled to -78°C was added dropwise, at such a rate as to keep the temperature below -60°C, 25 mL (61.5 mmol) 2.46 M n-butyUithium in hexanes. The reaction mixture was stirred at -78°C for ca. 30 minutes. To the reaction mixture was added dropwise a solution of 3.1 mT. (33 mmol) of N,N-dimethylcarbamyl chloride in 10 mL of THF at such a rate as to maintain the temperature below -65°C. The reaction mixture was aUowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to ca. 5°C and 60 mL of 50% ammonium

chloride solution was added. The reaction mixture was stirred for ca. 15 minutes. The pH was adjusted to ca. 3 with IN HCl (ca. 30 mL), and the aqueous phase was separated from the THF phase and extracted with ethyl acetate. The combined THF and ethyl acetate extracts were washed with brine, dried (MgS04) and concentrated ia vacuo to an oU. The oU was chromatographed on siHca with (20% ethyl acetate/80% n-butyl chloride) affording.4.33 g of the title compound as a pale yeUow soHd. iH NMR(CDC1 ₃ , 200 MHz.) δ: 6.61(d,lH), 6.46(d,lH), 4.62(bs,lH),

3.59(s,3H), 3.1(s,3H), 2.95(s,3H), 1.24(s,9H).

Example 18 3-{Aminoanlfonyl)-N.N.l- t.rirn^t ⁿ yl-lH-pyrrole-2-carbn7rpmiflp To a solution of 5.63 g of 3-[[(l,l-ά^nιethylethyl)amino]sulfonyl]- N,N,l-trimethyl-lH-pyrrole-2-carboxamide in 75 mL of methylene chloride was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated ia vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 4.21 g of the title compound as a gray soHd, m.p. 185-190.5°C. lH NMR(Me ₂ SO-de, 200 MHz.) δ: 6.99(bs,2H), 6.88(d,lH), 6.34(d,lH), 3.47(s,3H), 2.96(s,3H), 2.81(s,3H).

Exflrppk l ⁹ N-(l.l-Dimethylethyl)-l-methyl-lH A solution of 10 g (0.12 mol) of N-methyl-pyrrole in 120 mL of anhydrous THF under nitrogen atmosphere was cooled to below -70°C then treated with 56 mL of 2.4 M n-butyUithium in hexanes (0.13 mol) dropwise at such a rate as to keep the temperature below -60°C. The resulting brown colored mixture was stirred for 16 h at ambient temperature, then recooled to below -70°C at which time Hquified sulfur dioxide (9.0 mL, 0.21 mol) was added rapidly, causing an exotherm at - 20°C and the formation of a thick golden colored precipitate. After stirring for 1 h at ambient temperature, the THF was removed under

reduced pressure. The solids were triturated with ether and coUected by filtration with an ether rinse then dried under nitrogen. This intermediate sulfinate salt was added to a weU stirred mixture of 350 mL water and 250 mL dichloromethane chiUed to 0°C. N-Chlorosucci_nimide was then added in portions so as to keep the temperature below 3°C. The mixture was stirred vigorously for 30 min at ambient temperature, after which time, the layers were separated and the organic layer was washed successively with 10% aq NaHSθ3, twice with aq NaHCθ3, dried

(MgSθ4) and filtered. This dichloromethane solution was then cooled to

0°C and stirred whUe 32 mL (0.30 mol) of t-butylamine was added over 2 min. After stirring for 1 h at ambient temperature, soHds had precipitated from the brown solution which was then left stirring for 3 days. The mixture was dUuted with more dichloromethane then washed three times with IN HCl, once with saturated aq NaCl, dried (MgS04) and evaporated. The resulting soHd residue was triturated and coUected with a mixture of hexanes and n-chlorobutane to afford 7.4 g of the title compound as tan crystals, m.p. 125-126°C. H NMR (CDCI3, 200 MHz.) δ: 6.82 (m,lH), 6.78 (m,lH), 6.10 (m,lH),

4.53 (bs,lH), 3.83 (s,3H), 1.23 (s,9H). Methyl 2-rr(l.l-Dimethylethv1)amino1su1fonvn- l-methvl-lH-pvrrole-3-carboxvlate

To a solution of 2.5 g (11.5 mmol) of N-(l,l-dimethylethyl)-l- methyl-lH-pyrrole-2-suffonamide in 50 mT ^, THF under nitrogen atmosphere cooled to below -70°C was added dropwise 13 mL (32.5 mmol) of 2.5 M n-butyUithium at such a rate as to keep the temperature below

-58°C. After stirring at -20°C to -10°C for 30 min then 1 h at 0°C, the mixture was recooled to -70°C and treated with a solution of 1.63 g (17.3 mmol) of methyl chloroformate in 6 mL THF causing an exotherm to

-57°C. The reaction mixture was stirred overnight at ambient temperature then dUuted with 200 mL of ethyl acetate. This solution was washed successively with two 60 mL portions of IN HCl, brine, then dried (Na2S04) and evaporated to a dark oil. The crude product was

purified by chromatography on siHca gel (30% ethyl acetate/70% hexanes) then collected from hexanes to afford 0.45 g of the title compound, m.p. 105-108°C. iH NMR (CDCI3, 200 MHz.) δ: 7.00 (bs,lH), 6.61 (m,2H), 3.94 (s,3H),

3.85 (s,3H), 1.21 (s,9H). Example 21

Methyl 2-fAminnfliιlfonyl)-l-methyl- lH-pvrrole-3-carboxvlate A solution of 0.45 g (1.64 mmol) of methyl 2-[[(l,l- dimethylethyl)aπ-ino]sulfonyl]-l-πιethyl-lH-pyrrole-3-car boxylate in 20 mL TFA was prepared and stirred at ambient temperature for 3 hours. The TFA was then removed under reduced pressure and chloroform added to the residue and evaporated again to remove residual TFA The resulting soHd was suspended in water, filtered, and dried under vacuum to afford 0.25 g of the title compound, m.p. 119-121°C, (dec). !H NMR (Me ₂ SO-de, 200 MHz.) δ: 7.40 (bs,2H), 7.02 (d,lH), 6.48 (d,lH),

3.84 (s,3H), 3.76 (s,3H).

Example 22 carbonvnaminolsulfonvl-1-methyl-lH- pyτrote-3-carb9χylate

Methyl 2-(aminosulfonyl)-l-methyl-lH-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4,6-dimethoxy-2- pyrimidinyl)carbamate were combined in 2 T/ of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was dUuted with 15 mL of water and acidified with 0.5 mL IN HCl and the resulting precipitate was coUected by filtration and rinsed successively with water and ether, then dried to afford 0.15 g of the title compound as a white soHd, m.p. 192-193°C (dec). iH NMR (Me ₂ SO-d ₆ , 200 MHz.) δ: 12.7 (NH), 10.7 (NH), 7.22 (d,lH),

6.60 (d,lH), 6.02 (s,lH), 3.98 (s,3H), 3.96 (s,6H), 3.68 (s,3H).

F.yflm j 23

Methyl 2-rrrr(4-Methoxy-6-methyl-1.3.5-triazin- 2-vl^min l p bnnyηpminn ^g ιι1fonyl1-l-methvl-lH-pyrrole-3-carboxvlate Methyl 2-(aminosuHbnyl)-l-πιethyl-lH-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4-methoxy-6-methyl- l,3,5-triazin-2-yl)carbamate were combined in 2 mT/ of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was dUuted with 15 mL of water and acidified with 0.5 mL IN HCl and the resulting precipitate was coUected by filtration and rinsed successively with water and ether, then dried to afford 0.13 g of the title compound as a white soHd, m.p. 189-190°C (dec). iH NMR (Me ₂ SO-d ₆ , 200 MHz.) δ: 12.5 (NH), 11.1 (NH), 7.22 (d,lH),

6.60 (d,lH), 4.01 (s,3H), 3.98 (s,3H), 3.71 (s,3H), 2.49 (s,3H).

By applying the procedures of Examples 1 through 23 and

Equations 1 through 24, one skilled in the art can prepare the compounds in Tables 1 through 5. In the foUowing tables, abbreviations for various alkyl chains and rings have been used with the foUowing corresponding definitions. Et = ethyl = CH2CH3, iPr = isopropyl = CH(CH3)2, nPr = n-propyl = CH2CH2CH3, cPr = cyclopropyl = CH(CH2)2» cBu = cyclobutyl = CH(CH2)3, CC5H9 = cyclopentyl = CH(CH2)4- t-Bu = tert-butyl = C(CH3) ₃ n-Bu = n-butyl = (CH2)3CH3 cCρHii = cyclohexyl = CH(CH2)δ

R=H, R ¹ =CH ₃ , R ² =CO ₂ CH ₃ , R =H, R ⁷¹ =H

X

Z=CH

OCH ₃ CH ₂ S0 ₂ CH ₃

OCH ₃ cBu

CH ₃ 0(CH ₂ ) ₂ CH=CH ₂

SCH ₂ CF ₃ OCH ₃

SCHF ₂ CHg

CF ₃ CF ₃

CH ₂ CI OCH ₃

CH ₂ Br OCH ₃

CH ₂ F OEt

I OCH ₃

OCH ₂ CHF ₂ CH ₃

NHiPr CH ₃

N(iPr) ₂ CH ₃

OCH ₂ CF ₃ OCH ₂ CF ₃

NEt ₂ NEt ₂

OCH _{3 3}

CH ₃ cPr

CH ₃ CH2SEt

OCH ₃ cC ₅ H ₉

C CH ₂ ) ₃ C1 O(CH ₂ ) ₃ Cl

_fi 22 _fl 3 _fi 23 _Q 4 _fi 24

_fi 22 Q3 Q4

Z=CH

fi ²² Q? a. ⁴

R ² =C0 ₂ CH ₃ , R ⁷¹ =H, R=R ⁴ =H, R=H, R ¹ =CH ₃ , R ⁷¹ =H, R ² =C0 ₂ C ₂ H ₅ , R ¹ =CH ₂ OCH ₃ R ⁴ =H

X

R=R ⁴ =H, R ⁷¹ =H, R ² =S0 ₂ CHg, R=H, R =H, R ¹ =CHg, R ⁷¹ =H, R ¹ =CH ₃ R ² =S0 ₂ N(CH ₃ ) ₂

R=H, R^CHg, R =H, R ⁷¹ =H, R=H, R ¹ =CH ₃ , R =H, R ⁷¹ =H, R ² =C(0)CH ₃ R ² =C(H)=NOCH ₃

CHg

CH ₃

R ¹ =CH ₃ , R ⁷¹ =H, R ² =CH ₂ S0 ₂ CH ₃ , R ¹ ^^, R =H, R ⁷¹ =H, R ² =CH ₂ OH R ⁴ =H

B B

R ¹ =CH ₃ , R ⁷¹ =H, R ² =CHF ₂ , R =H R ¹ =CH ₃ , R ⁴ =H, R ⁷¹ =H, R ² =CN

B X B

R=H, R ⁴ =H, R ⁷¹ =H, R- ^~ CH ₃ , R ² =SCHg R=H, R ⁴ =H, R ¹ =CH ₃ , R ⁷¹ =H, R ² =C(0)N(CH ₃ ) ₂

X

R^H, R ⁷¹ =H, R ² =C0 ₂ CH ₃ , R ⁴ =H R ¹ =H, R ⁴ =H, R ⁷¹ =H, R ² =S0 ₂ N(CH ₃ ) ₂

B B

R^R^H, R ⁷¹ =H, R ² =CHO R ¹ =R ⁴ =H, R ⁷¹ =H, R ² =C0 ₂ Et

B X B

X=Y=OCH ₃ , Z=CH, R=H, R ⁷¹ =H

B ¹ B ² B ⁴

X=CH ₃ , Y=OCH ₃ , Z=N, R=H, R ¹ =CH ₃ , R4=H, R2= _B (CH ₂ ) _m ² , R ⁷¹ =H

ffi Q2 _E 45 _S 46 _E 47 _£ 48

X=OCH ₃ , Y=OCH ₃ , Z=N, R=H, R ¹ =CH ₃ , 4=H, R ² =(CH ₂ ) _m Q ² , R ⁷¹ =H

m _∑ Q? £49 _E 50 _E 51 _E 52 _S 53 _E 54 _E 55

H H3 H

X=.γ=OCH ₃ , Z=CH, R=R4=H, R ¹ =CH ₃ , R2=(CH ₂ ) _m Q ² , R71=H

« r

X=CH ₃ , Y=OCH ₃ , Z=CH, R=R4=H, Rl=CH ₃ , R2=(CH ₂ ) _m Q ² , =0, R71=H

Q2 _π 4 _E 59 _E 60 _E 61 _E 62 _E 63 _E 64 _fi 65

X=Y=OCH ₃ , Z=CH, R=R4=H, R2=C0 ₂ CH ₃ , R71=H

Ql.l R 5= 26 _=H

Ql-1 R 5 ₌ 4-C1, 26=H

Ql-4 q=0, R ₌ 28 _=H

Ql-5 29 _β R30 _=R 31 ₌ H

Ql-6 R32 _β R33 _=H

Ql-8 Wl=0, R34=R35 ₌ R36 _=H

Ql-8 Wl=S, R34=R35 ₌ R36 _=H

Ql-9 Wl=S, R34=R35 _=R 36 ₌ H

Qi-10 R 7=H, 38=CH ₃

Ql-11 R39 ₌ SCH ₃

Qi-lδ W ² =S, R63=R64 _=H

Ql-21 R65 ₌ CH ₃

TΔE E.2

R=H, R ¹ =CH ₃ , R ² =SO ₂ N(CH ₃ ) ₂ , R ⁴ =H, R ⁷¹ =H

X z.

CH ₃ CH3 CH NHCH3 OCH3 N

CH ₃ OCH3 CH N(CH ₃ ) ₂ OCH3 N

OCH3 OCH3 CH C2H5 OC ₂ H ₅ N

Cl OCH3 CH NHCH3 OC ₂ H ₅ N

CH ₃ OC ₂ H ₅ CH N(CH ₃ ) ₂ OC ₂ H ₅ N

C ₂ H ₅ OCH3 CH NHCH3 OCH ₂ CF ₃ N

H OCH3 CH N(CH ₃ ) ₂ OCH ₂ CF ₃ N

H OC ₂ H ₅ CH CH3 OC ₂ H ₅ N

OCH3 CH ₂ OCH ₃ CH CF3 OCH3 N

CH3 CH(OCH ₃ ) ₂ CH OCF ₂ H OCH3 N

OCHF ₂ OCH3 CH CH3 OCH ₂ CH=»CH2 N

OCH3 SCH3 CH

CH ₃ OCH3 N

OCH3 OCH3 N

R=R ⁴ =H, R ⁷¹ =H, R ² =S0 ₂ CH ₃ , R ¹ =CH ₃ R=R ⁴ =H, R ¹ =CH ₃ , R =Br, R ⁷¹ =H

X X

R ¹ =CH ₃ , R ⁴ =H, R ⁷¹ =H, R ² =CHO R ¹ =CH ₃ , R ⁴ =H, R ⁷¹ =H, R ² =CHF ₂

E B

R ¹ =CH ₃ , R =H, R ⁷¹ =H, R ² =CH ₂ OCH ₃ R ¹ =CH ₃ , R ⁴ =H, R ⁷¹ =H, R ² =CH ₂ CN

B B

X=Y=OCH ₃ , Z=CH, R=H, R71 _=H

E ¹ E ² E ⁴

TABLE 3

R=H, R!=CH ₃ , R ² =C0 ₂ CH ₃ , R ³ =H, R ⁷¹ =H

Z=CH X

OCH ₃ CH2S0 ₂ CH ₃

OCH ₃ cBu

CH ₃ 0(CH ₂ ) ₂ CH=CH ₂

SCH ₂ CF ₃ OCH ₃

SCHF ₂ CH ₃

CF ₃ CF ₃

CH ₂ CI OCH ₃

CH ₂ Br OCH ₃

CH ₂ F OEt

I OCH ₃

OCH ₂ CHF ₂ CH ₃

NHiPr CH ₃

N(iPr) ₂ CH ₃

OCH ₂ CF ₃ OCH ₂ CF ₃

NEt ₂ NEt ₂

OCH ₃ Ng

CH ₃ cPr

CH ₃ CH ₂ SEt

OCH ₃ cC ₅ H ₉ c CH ₂ ) ₃ CKCH ₂ ) ₃ α

R=R ³ =H, R ⁷¹ =H, R ¹ =CH ₂ OCH ₂ CH _3> R=H, R!=CH ₃ , R ⁷¹ =C1, R ³ =H, R ² =C0 ₂ Et R ² =C0 ₂ Et

R=R ³ =H, R ⁷¹ =H, R ¹ =CH ₃ , R ² =S0 ₂ CH ₃ R=R ³ =H, R^CH^ R ⁷¹ =H, R ² =S0 ₂ N(CHg) ₂

R=R ³ =H, R ⁷¹ =H, R ² =C(O)CH ₃ R=R ³ =H, R!=CH ₃ , R ⁷¹ =H, R ² =C(OCH ₃ )=NOCH ₃

R!=CH _3> R ³ =H, R ⁷¹ =H, R ² =N0 ₂ R!=CH ₃ , R ³ =H, R ⁷ⁱ =H, R ² =S(0)Et

B X B

E X E X

R ¹ =CH _3> R ³ =H, R ⁷ 1=H, R ² =C1 R ¹ =CH ₃ , R ³ =H, R ⁷¹ =H, R ² =CH ₂ OCH ₃

B B

R1=CH _3I R ³ =H, R ⁷ 1=H, R ² =SC ₂ H ₅ R!=CH ₃ , R ³ =H, R ⁷¹ =H, R ² =CHF ₂

B B X

R ¹ =C ₂ H ₅ R ³ =R ⁷¹ =H, R ² =OCH ₃ R!=CH ₃ , R ³ =R ⁷¹ =H, R ² =OC O)CH ₃

B B

R ¹ =CH ₃ , R =R ⁷¹ =H, R ² =OS0 ₂ CH ₃ R ¹ =CH ₃ , R ³ =R ⁷¹ =H, R ² =OiPr

£ £

X=Y=OCH ₃ , Z=CH, R=H, R ⁷ 1=H

TABI.E

o

II J-S(0) ₂ NHCN-A

R

R=H, Rl=CH ₃ , R3=R ₌ H, R2=C0 ₂ CH ₃ , R?1=H

Δ X ¹ γi X ³

R=H, R ¹ =CH ₃ , R3=R4=H, R2=C0 ₂ CH ₃ , R^H

*L Δ ¹ X ¹ X ³

J-3 A-5 CH ₂ CF ₃ OCH3

TABlJjg

R3=R4=H, Rl=CH ₃ , R ⁷¹ =H

E ² Σ

The procedures of Examples 1 through 18 and Equations 1 through 21 were followed in the synthesis of the following compounds.

INDEX TABLE

J is J-2, Rl is CH ₃ , R ⁴ and R ⁷ 1 are H

²

GMED E ² X 2 2UCJ

^{1 2} 71

⁷¹

?71

CMEDE E E 71 m.p.CC)

JisJ-3,R ⁷¹ isH

£MEE E ¹ E ² E ⁴ m.p.(°C)

180 CH ₃ C0 ₂ CH ₃ H 181-183

181 CH ₃ C0 ₂ CH ₃ H 216-218

182 CH ₃ SO ₂ N(CH ₃ ) ₂ H 223-225

183 CH ₃ SO ₂ N(CH ₃ ) ₂ H 207-209

184 CH ₃ SO ₂ N(CH ₃ ) ₂ H 204-206

185 CH ₃ S0 ₂ N(CH ₃ ) ₂ H 206-208

186 CH ₃ S0 ₂ N(CH ₃ ) ₂ H 185-187

187 CH ₃ S0 ₂ N(CH ₃ ) ₂ H 176-178

188 CH ₃ SO ₂ N(CH ₃ ) ₂ H 166-168

189 CH ₃ S0 ₂ N(CH ₃ )2 H 143-145

190 CH ₃ S0 ₂ N(CH ₃ ) ₂ H 174-176

191 CH ₃ SO ₂ N(CH ₃ ) ₂ H 178-180

192 CH ₃ SO ₂ N(CH ₃ ) ₂ H 213-215

193 CH ₃ C(0)N(CH ₃ ) ₂ H 190-196

194 CH ₃ C(O)N(CH ₃ ) ₂ H 170-176

195 CH ₃ C(O)N(CH ₃ ) ₂ H 193-197

196 CH ₃ C(O)N(CH ₃ ) ₂ H 143-145

197 CH ₃ C(OJN(CH ₃ ) ₂ H 123-125

198 CH ₃ C(0)N(CH ₃ ) ₂ H 139.5-142.5

199 CH ₃ C(O)N(CH ₃ ) ₂ H 189-196

200 CH ₃ C(O)N(CH ₃ ) ₂ H 154.5-162

201 CH ₃ C(O)N(CH ₃ ) ₂ H 183-185

202 CH ₃ C(O)N(CH ₃ ) ₂ H 127-129

203 CHg S0 ₂ CHg H CH ₃ CHg CH 215-216 204 CH ₃ S0 ₂ CH ₃ H CH ₃ OCH ₃ CH 211-212 205 CH ₃ S0 ₂ CH ₃ H OCHg OCHg CH 224-226

^{; 4}

^{2 4}

CMED E ¹ E E ⁴ m.p.fC)

268 Et C0 Et H OCH ₃ OCH ₃ N 174-175 269 Et C0 ₂ Et H CT OCH ₃ CH 181-182 270 CH ₂ OCH ₃ S0 ₂ CH ₃ H CH ₃ CHg CH 182-189 271 CH ₂ OCH ₃ S0 ₂ CH ₃ H CH ₃ OCHg CH 162-169 272 CH ₂ OCH ₃ SO ₂ CH ₃ H OCH ₃ OCHg CH 179-187 273 CH ₂ OCH ₃ S0 ₂ CH ₃ H CH ₃ OCHg N 167-170 274 CH ₂ OCH ₃ S0 ₂ CH ₃ H OCH ₃ OCHg N 195-198 275 CH ₂ 0CH ₃ S0 ₂ CH ₃ H CT COHg CH 187-192 276 Et C0 ₂ CH ₃ H NHCH ₃ OEt N 188-190 277 Et C0 ₂ CH ₃ H N(CH ₃ ) ₂ OEt N 171-174 278 Et C0 ₂ CH ₃ H N(CH ₃ ) ₂ OCH2CFg N 186-188 279 CH ₃ C0 ₂ iPr H N(CH ₃ ) ₂ OCH ₂ CFg N 167-169 280 Et C0 ₂ Et H NHCH ₃ OEt N 162-164 281 Et C0 ₂ Et H N(CH ₃ ) ₂ OCH ₂ CFg N 178-180 282 CH ₃ C0 ₂ Et H N(CH ₃ ) ₂ OCH ₂ CFg N 173-174 283 CH ₃ C0 ₂ CH ₃ Br CH ₃ CHg CH 148-150 284 CH ₃ C0 ₂ CH ₃ Br CH ₃ OCHg CH 137-140 285 CH ₃ C0 ₂ CH ₃ Br OCH ₃ OCHg CH 154-156 286 CH ₃ C0 ₂ CH ₃ Br CH ₃ OCHg N 150-151 287 CH ₃ C0 ₂ CH ₃ Br OCH ₃ OCHg N 157-160 288 CH ₃ CO ₂ CH ₃ Br Cl OCHg CH 152-155 289 CH ₃ C0 ₂ CH ₃ Br N(CH ₃ ) ₂ OEt N 145-147

J ia J-3, R ⁷¹ ia H

290 CH ₃ SCH ₃ H CH ₃ COH ₃ CH 217-220 291 CH ₃ SCH ₃ H OCH ₃ OCH ₃ CH 230-235 292 CH ₃ SCH ₃ H CHg OCH ₃ N 186-189 293 CH ₃ SCH ₃ H Cl OCH ₃ CH 188-190

C ED E ¹ E ² E mjiΛlΩl

315 Ph CO ₂ CH ₃ H CH ₃ CH ₃ CH 209-212 316 Ph C0 ₂ CH ₃ H CH ₃ OCH ₃ CH 212-215 317 Ph C0 ₂ CH ₃ H OCH ₃ OCH ₃ CH 185-188 318 Ph C0 ₂ CH ₃ H CHg OCH ₃ N 165-170 319 Ph C0 ₂ CH ₃ H OCHg OCH ₃ N 160-164

t

CMEfi E ¹ E ² E ⁴ X m.p.rC)

338 CH ₃ CN CO ₂ CH ₃ CH ₃ OCH ₃ CH >260 339 CH ₃ CN C0 ₂ CH ₃ OCH ₃ OCH ₃ CH 183-185 340 CH ₃ CN C0 ₂ CHg CH ₃ OCH ₃ N 180-183 341 CH ₃ CN C0 ₂ CHg OCH ₃ OCH ₃ N 231-235 342 CHg CN C0 ₂ CHg Cl 0CH ₃ CH >255

Ji8J-2,R ⁷¹ iBH

CMPDR ¹ E ² E ⁴ m.p.ro

343 Ph S0 ₂ CH ₃ H CH ₃ OCH ₃ CH 225-226 344 Ph S0 ₂ CH ₃ H OCH ₃ OCH ₃ CH 212-216 345 Ph S0 ₂ CH ₃ H CH ₃ OCH ₃ N 199-201 346 Ph SO ₂ CH ₃ H OCH ₃ CT CH 209-211

JisJ-3,R ⁷¹ isH

CMEΠE ¹ B E ⁴ X m.p.CC)

347 CH ₃ CN CHO CHg OCH ₃ CH 179-180 348 CH ₃ CN CHO OCHg OCHg CH 181-184 349 CH ₃ CN CHO CH ₃ OCH ₃ N 229-233 350 CH ₃ CN CHO CT COH ₃ CH 155-159

isJ-2,R ⁷¹ isH

^{1 2 4}

JisJ-3,R ⁷¹ i8H

J is J-2, R ⁷¹ is H

GMEH E ¹ E ² E ⁴ m.p.( ^e C)

384 CH ₃ C(=0)N(CH ₃ ) ₂ H CH ₃ CH ₃ CH 159-166

385 CH ₃ C(=0)N(CH ₃ ) ₂ H CH ₃ OCH ₃ CH 131-136

386 CH ₃ C(=0)N(CH ₃ ) ₂ H OCH ₃ OCH ₃ CH 140-147

387 CH ₃ C(=0)N(CH ₃ ) ₂ H Cl OCH ₃ CH 103-107

388 CH ₃ C(=0)N(CH ₃ ) ₂ H CH ₃ OCH ₃ N oil

389 CH ₃ C(=0)N(CH ₃ ) ₂ H OCH ₃ OCH ₃ N oil

390 CH ₃ C(=0)N(CH ₃ ) ₂ H NHCH ₃ OEt N 140-142

391 CH ₃ C(=0)N(CH ₃ ) ₂ H N(CH ₃ ) ₂ OEt N 178-180

392 CH ₃ C(=0)N(CH ₃ ) ₂ H OEt OEt N 121-125

393 CH ₃ C(=O)N(CH ₃ ) ₂ H NHCH ₃ OCH ₂ CF ₃ N 155-160

394 CH ₃ C(=0)N(CH ₃ ) ₂ H N(CH ₃ ) ₂ OCH ₂ CF ₃ N 250

395 CH ₃ C(=O)N(CH ₃ ) ₂ H N(CH ₃ ) ₂ OCH ₃ N gum

396 CH ₃ C(=0)N(CH ₃ ) ₂ H Et OEt N gum

397 CH ₃ C(=0)N(CH ₃ ) ₂ H Et OCH ₃ N gum

398 CH ₃ CHO H CH ₃ OCH ₃ CH 140-141.5

399 CH ₃ CHO H OCH ₃ OCH ₃ CH 172-174.5

400 CH ₃ CHO H CT OCH ₃ CH 172-175

401 CH ₃ CHO H CH ₃ OCH ₃ N 156-160

402 CH ₃ CHO H OCH ₃ OCH ₃ N 173-177

403 CH ₃ CHO H NHCH ₃ OEt N 176-179

404 CH ₃ CHO H OEt OEt N 102-104

405 CH ₃ CHO H Et OEt N 149-151.5

406 CH ₃ CHO H Et OCH ₃ N 148-150

CMEΠ R ¹ E ² R ⁴ X m.p.f'C)

CH ₃ CH 179-180 OCH ₃ CH 181-184 CH ₃ N 229-233 CT CH 155-159

CHg CH 92-95 OCHg CH 168-171 CH ₃ N 120-123 CT CH 165-170 N(CH ₃ ) ₂ N 129-131

^{1 4}

GMED. R ¹ E ² R ⁴ m.p.fC)

OCH ₃ CH ₃ CH 172-173 OCH ₃ OCH ₃ CH 183-184 CH ₃ OCH ₃ N 189-190 OCH ₃ OCH ₃ N 193-194

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to severed hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

i r n *

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

* Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are some-

times desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufac- tuf ed, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and

Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples lOthrough 41;

R. W. Luckenbaugh, U.S. Patent 3,309,192, Marchl4, 1967, Col. 5, line 43 through Col. 7, hne 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, Hne 17 and Examples 1-4; G. C. KHngman, "Weed Control as a Science", John Wiley and Sons,

Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

Example A High Strength Concentrate methyl 3-[[[[(4,6-dirnethoxy-2-pyιin_ύdmyl)amino]- carbonyl]amino]sulfonyl]-l-methyl-lH-pyrrole-2- carboxylate 99% trimethylnonyl polyethylene 1% glycol ether The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U. S. S. no. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

Pimple ft Wettable Powder methyl 3[[[[[4-ethoxy-6-(methylamino)-l,3,5-triazin-2- yl]amino]carbonyl]amino]sulfonyl]- 1-methyl- lH-pyrrole- 2-carboxylate 65% dodecylphenol polyethylene glycol ether 2% sodium Hgninsulfonate 4% sodium siHcoaluminate 6% montmorillonite (calcined) 23%

The ingredients are thoroughly blended. The Hquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged. Example C

Aqueous Suspension methyl 3-[[[C(4,6-din_ιethoxy.2-pyr-jnidinyl)amino]- carbonyl]am_ino]suKonyl]-l-methyl-lH-pyrrole-2- carboxylate 50.0% polyacryHc acid thickener 0.3% dodecylphenol polyethylene 0.5% glycol ether disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%

The ingredients are blended and ground together in a sand mill to produce particles essentiaUy aH under 5 microns in size.

Exqmple T) Oil Suspension πιethyl 3[[[[[4-ethoxy-6-(nιethylamino).l,3,5-triazin-2- yl]amino]carbonyl]amino]sulfonyl]-l.methyl.lH-pyrrole- 2-carboxylate 35% blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates 6% xylene 59%

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

Example E

Oil Suspension methyl 3-[[[[(4,6-dirnethoxy-2-p3rriιnid--αyl)arj_ιino]- carbonyl]amino]sulfonyl]-l-methyl-lH-pyrrole-2- carboxylate 25% polyoxyethylene sorbitol hexaoleate 5% highly aHphatic hydrocarbon oil 70%

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

Example F Aqueous Suspension methyl 3[[[[[4-ethoxy-6-(methylamino)-l,3 ,5-triazin-2- yl]an_ύno]carbonyl]amino]sulfonyl]-l-methyl-lH-pyrrole- 2-carboxylate 25% hydrated attapulgite 3% crude calcium ligninsulfonate 10% sodium dihydrogen phosphate 0.5% water 61.5%

The ingredients are ground together in a ball or roUer null until the soHd particles have been reduced to diameters under 10 microns.

_Exam£l≤_G_ Wettable Powder m^ethyl 3-[[[[(4,6-din.ιethoxy-2-pyrimidinyl)amino]- carbonyl]amino]sulfonyl]-l-methyl-lH-pyrrole-2- carboxylate 40.0% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3% low viscosity methyl cellulose 1.5% attapulgite 54%

The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

AU compounds of the invention may be formulated in the same manner.

yflτnp1? H Granule wettable powder of Example G 15% gypsum 69% potassium sulfate 16%

The ingredients are blended in a rotating mixer and water sprayed on to accompHsh granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S.#18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.

Wettable Po der methyl 3[[[[[4-ethoxy-6-(methylammo)-l,3,5-tri.azin-2- yl]an__dno]carbonyl]amino]suuOnyl]-l-nietiiyl-lH-pyrrole- 2-carboxylate 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46%

The ingredients are blended, coarsely hammer-miUed and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

F-gflmplf. J

Extruded PeHet methyl 3-[[[[(4,6-d-unethoxy-2-pyr.jmdmyl)amino]- carbonyl]amino]su]fonyl]-l-methyl-lH-pyrrole-2- carboxylate 25% anhydrous sodium sulfate 10% crude calcium ligninsulfonate 5% sodium alkylnaphthalenesulfonate 1% calcium/magnesium bentonite 59%

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

Example K Wettable Powder methyl 3[[[[[4-ethoxy-6-(methylamino)-l,3,5-triazin-2- yl]ammo]carbonyl]amino]suuOnyl]-l-methyl-lH-pyrrole-2- carboxylate 80% sodium alkylnaphthalenesulfonate 2% sodium Hgninsulfonate 2% synthetic amorphous silica 3% kaolinite 13%

The ingredients are blended and then ground in ahammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.

Example

High Strength Concentrate methyl 3-[[[[(4,6-d_unethoxy.2-pyrimidinyl)amino]- carbonyl]amino]sulfonyl]-l-nιethyl-lH-pyrrole-2- carboxylate 98.5% siHca aerogel 0.5% synthetic amorphous fine silica 1.0%

The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentiaUy all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.

Solution methyl 3[[[[[4-ethoxy-6-(methylamino)-l,3 ,5-triazin-2- yl]an__bi o]carbonyl]an ino]sulfonyl]-l-ιnethyl-lH-pyrrole- 2-carboxylate sodium salt 5% water 95%

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

F.τflτnp

Solution ιnethyl 3-[[[[(4,6-dinιethoxy-2-pyrin__ddinyl)amino]- carbonyl]ammo]suHonyl]-l-methyl-lH-pyrrole-2- carboxylate sodium salt 5% water 95%

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

Utility

Test results indicate compounds of this invention are active postemergence and preemergence herbicides. Compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include, but are not limited to barley (Hordes vulgare). cotton f / ^g ftypju,τη hirsutum). rape ⁽ Brassica napiis), rice ⁽ Oryza sativa ⁾ . and wheat ⁽ Tritjcy , .agsϋmsa). Grass and broadleaf weed species controUed include, but are not limited to, bedstraw f alin spp.), brome (Bromus spp.), lambsquarters and umbrella sedge (Cyperus spp.). A few compounds in this invention are useful for the control of selected broadleaf weeds such as umbrella sedge in upland and paddy rice.

These compounds also have utility for control of vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth or as citrus abscission agents.

A herbicidaUy effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of appHcation, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of the subject compounds is appHed at rates from 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha. One skiUed in the art can easUy determine application rates necessary for the desired level of weed control. Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The foUowing list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control.

Common Nam

acetochlor 2-chloro-N-(ethoxymethyl)-N- (2-ethyl-6-methylphenyl)acetamide

acifluorfen 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoic acid

acrolein 2-propenal

alachlor 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamide

anilofos S-4-chloro-N-isopropylcarbanUoyl- methyl-0,0-dimethyl phosphorodi- thioate

ametryn N-ethyl-N'-(l-methylethyl)-6- (methylthio)-l,3 ,5-triazine-2 ,4- diamine

amitrole lH-l,2,4.triazol-3-amine

AMS ammonium sulfamate

asulam methyl [(4-aminophenyl)sulfonyl]- carbamate

atrazine 6<hloro-N-ethyl-N ^, -(l-methylethyl)- 1 ,3 ,5-triazine-2 ,4-diamine

barban 4-chloro-2-butynyl 3-chlorocarbamate

benefin N-butyl-N-ethyl-2,6-dinitro-4<tri- fluoroπιethyl)benzenamine

25 bifenox methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoate

bromacil 5-bromo-6-methyl-3-(l-methylpropyl)-

30 2,4(lH,3H)p3rrimidinedione

bromoxynil 3 ,5-dibromo-4-hy droxybenzonitrile

butachlor N-(butoxymethyl)-2-chloro-N-(2,6-

35 diethylphenyl)acetamide

buthidazole 3-[5-(l,l-dimethylethyl)-l,3,4-thia- diazol-2-yl]-4-hydroxy-l-methyl-2- imidazoHdinone

40 butralin 4-(l,l-dimethylethyl)-N-(l-methyl- propyl)-2,6-dinitrobenzenamine

butylate S-ethyl bis(2-methylpropyl)- carbamothioate

45

dimethyl arsinic oxide

2-chloro-N,N-di-2-propenylacetamide

2-chloroaUyl diethyldithiocarbamate

3-(4,6-dimethoxy-l,3 ,5-triazin-2-yl)- l-[2-(2-methoxyethoxy)-pehnyl- sulfonyl]-urea

3-amino-2,5-dichlorobenzoic acid

3-(4-bromo-3-chlorophenyl)-l-methoxy-l- methylurea

2-[[[[(4-chloro-6-methoxy-2-pyrimi- dinyl)ethylamino]carbonyl]- amino]sulfonyl]benzoic acid, ethyl ester

2,4-dichlorophenyl 4-nitro-3- methoxyphenyl ether

2,4,6-trichlorophenyl-4-nitro- phenyl ether

N'-[4-(4-chlorophenoxy)phenyl]-N,N- dimethylurea

1-methylethyl 3-chlorophenylcarbamate

2-chloro-N-[[(4-methoxy-6-methyl-l,3,5- triazin-2-yl)amino]carbonyl]benzene- sulfonamide

N'-(3-chloro-4-methylphenyl)-N,N- dimethylurea

propylamino)-s-triazine cyprazole N-[5-(2-chloro-l,l-dimethylethyl)-l,3,4- thiadiazol-2-yl]cyclopropanecarbox- amide

cypromid 3',4'-dichlorocyclopropanecarboxaniHde

dalapon 2,2-dichloropropanoic acid

πnm πη ™*

dazomet tetrahydro-3,5-dim.ethyl-2H-l,3,5-thia- diazine-2-thione DCPA dimethyl 2 ,3 ,5 ,6-tetrachloro- 1 ,4-benzene- dicarboxylate

desmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyljcarbamate

desmetryn 2-(isopropylamino)-4-(nιethylamino)-6- (methylthio)-a-triazine

diaUate S-(2,3-dichloro-2-propenyl)bis(l- methylethyl)carbamothioate

dicamba 3,6-dichloro-2-metho^benzoic acid

dichlobeml 2,6-dichlorobenzonitrile

dichlorprop (±)-2-(2,4-dichlorophenoxy)propanoic acid

dichlofop (±)-2-[4-(2,4-dichlorophenoxy)phenoxy3- propanoic acid, methyl ester

diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)- glycine

difenzoquat l,2-dimethyl-3,5-diphenyl-lH-pyrazoHum

dimepiperate S-1-methyl-l-phenylethylpiperidine- 1-carbothioate

dinitramine N ³ ,N ³ -diethyl-2,4-dinitro-6-(trifluoro- methyl)-l,3-benzenediamine

dinoseb 2-(l-methylpropyl)-4,6-dinitrophenol

diphenamid N,N-dimethyl-a-phenylbenzeneacetamide

ethofumesate (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 5-benzofuranyl methanesulfonate

fenac 2,3,6-trichlorobenzeneacetic acid

fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]propanoic acid

fenuron N,N-dimethyl-N'-phenylurea

fenuron TCA Salt of fenuron and TCA

methyl)phenyl]-4( lH)-pyridinone

fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamide

fosamine ethyl hydrogen (aminocarbonyl)- phosphate

glyphosate N-(phosphonomethyl)glycine

haloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid

hexaflurate potassium hexafluoroarsenate

< mfflpn N?m* C-hgπricnl flT ? hexazinone 3-cyclohexyl-6-(dimethylamino)-l-methyl- l,3,5-triazine-2,4(lH,3H)-dione

imazametha- 6-(4-isopropyl-4-methyl-5-oxo-2- benz imidazolin-2-yl)-iB-toluic acid, methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazoHn-2-yl)- p_-toluic acid, methyl ester

imazapyr (±)-2-[4,5-dihydro-4-methyl-4-(l-methyl- ethyl)-5-oxo-lH-imidazol-2-yl]-3- pyridinecarboxylic acid

imazaquin 2-[4 ,5-dihydro-4-methyl-4-( 1-methyl- ethyl)-5-oxo-lH-imidazol-2-yl]-3- quinolinecarboxylic acid

imazethapyr (±)-2-[4,5-dihydro-4-methyl-4-(l-methyl- ethyl)-5-oxo-lH-imidazol-2-yl]-5- ethyl-3-pyridinecarboxyHc acid

ioxynil 4-hydroxy-3 ,5-duodobenzonitrile

isopropalin 4-(l-methylethyl)-2,6-dinitro-N,N- dipropylbenzenamine

isoproturon N-(4-isopropylphenyl)-N ^, ,N'-dimethylurea

isouron N'-[5-(l,l-dimethylethyl)-3-isoxazolyl]- N,N-dimethylurea

isoxaben N-[3-(l-ethyl-l-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamide

karbutilate 3-[[(diπιethylamino)carbonyl]anιino]- phenyl-(l,l-dimethylethyl)carbamate

lactofen (±)-2-ethoxy-l-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoate

Chemical Name

3-cyclohexyl-6,7-dihydro-lH-cyclopenta- pyrimidine-2,4(3H,5H)-dione

N'-(3,4-dichlorophenyl)-N-methoxy-N- methylurea

methylarsonic acid

monoammonium salt of MAA

(4-chloro-2-methylphenoxy)acetic acid

4-(4-chloro-2-methylphenoxy)butanoic acid

S,S-dimethyl-2-(difluoromethyl)-4- (2-methylpropyl)-6-(trifluoromethyl)- 3 ,5-pyridinedicarbothionate

(±)-2-(4-chloro-2-methylphenoxy)- propanoic acid

mefenacet 2-(2-benzothiazolyloxy-N-methyl-N- phenylacetamide

mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)- sulfonyl]armno]phenyl]acetamide

methal- N-(2-methyl-2-propenyl)-2,6-dinitro-N- propaHn propyl-4-(trifluoromethyl)benzenamide

methabenz- l,3-dimethyl-3-(2-benzothiazolyl)urea thiazuron

metham methylcarbamodithioic acid

methazole 2-(3,4-dichlorophenyl)-4-methyl-l,2,4- oxadiazolidine-3 ,5-dione

Ch miyfll λ ,?

N'-(3-chloro-4-methoxyphenyl)-N,N- dimethylurea

2-chloro-N-(2-ethyl-6-methylphenyl)-N- (2-methoxy-l-methylethyl)acetamide

4-amino-6-(l,l-diπιethylethyl)-3-(πιethyl- thio)-l ,2 ,4-triazin-5(4H)-one

2-[[[[(4-methoxy-6-methyl-l,3,5-tri- azin-2-yl)amino]carbonyl]- amino]sulfonyl]benzoic acid, methyl ester

l,2-dihydro-3,6-pyridazinedione

S-ethyl hexahydro-lH-azepine-1-carbo- thioate

3-(E-chlorophenyl)-l-methoxy-l-methyl- urea

N'-(4-chlorophenyl)-N^-dimethylurea

Salt of monuron and TCA

MSMA monosodium salt of MAA

35 napropamide N,N-diethyl-2-(l-naphthalenyloxy)- propanamide

naptalam 2-[( l-naphthalenylamino)carbonyl]- benzoic acid

40 neburon l-butyl-3-(3,4-dichlorophenyl)-l-methyl- urea

nicosulfuron 2-[[(4,6-dimethoxypyrimidin-2-yD-

45 aminocarbonyl]aminosulfonyl]-N,N- dimethyl-3-pyridinecarboxamide

Common Nam Che.τn.ra) ^TΠ

nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N- dipropylaniHne

nitrofen 2,4-dichloro-l-(4-nitrophenoxy)benzene

nitrofluorfen 2-chloro-l-(4-nitrophenoxy)-4-(tri- fluoromethyDbenzene

norea N,N-dimethyl-N'-(octahydro-4,7-methano- lH-inden-5-yl)urea 3aa,- 4a,5a,7a,7aa-isomer

norflurazon 4-chloro-5-(methylamino)-2-[3-(tri- fluoromethyl)phenyl]-3(2H)- pyridazinone

oryzalin 4-(dipropylamino)-3 ,5-dinitro- benzenesulfonamide

oxadiazon 3-[2,4-dichloro-5-(l-methylethoxy)- phenyl]-5-(l,l-dimethyIethyl)- 1,3 ,4-oxadiazol-2(3H)-one

oxyfluorfen 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene

paraquat l,l'-dimethyl-4,4'-dipyridinium ion

pebulate S-propyl butylethylcarbamothioate

pendimethalin N-(l-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamine

perfluidone l,l,l-trifluoro-N-[2-methyl-4-(phenyl- su FonyDphenyllmethanesulfonamide

phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamate

C mon Name _ ^ftτ nicffl ^N aπift picloram 4-amino-3,5,6-trichloro-2-pyridine- carboxyHc acid

PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl ester

pretilachlor a-chloro-2,6-diethyl-N-(2-propoxy- ethyDacetanilide

procyazme 2-[[4-chloro-6-(cyclopropylamino)-l,3,5- triazine-2-yl]amino]-2-methylpropane- nitrile

N-(cyclopropylmethyl)-2,6-dinitro-N- propyl-4-(trifluoromethyl)benzenamine

6-methoxy-N,N'-bis(l-methylethyl)-l,3,5- triazine-2 ,4-diamine

N,N'-bis(l-methylethyl)-6-(methylthio)- 1 ,3 , 5-triazine-2 ,4-diamine

3,5-dichloro-N-(l,l-dimethyl-2-propyn- yDbenzamide

2-chloro-N-(l-methylethyl)-N- phenylacetamide propanil N-(3 ,4-dichlorophenyl)propanamide

propazine 6-chloro-N,N'-bis( 1-methylethyl)- 1 ,3 , 5-triazine-2 ,4-diamine

propham 1-methylethyl phenylcarbamate

Common, fl ^ em ^l Name prosulfalin N-[[4-(dipropylamino)-3 ,5-dinitro- phenyl]sulfonyl]-S ,S-dimethylsulfil- imine

prynachlor 2-chloro-N-(l-methyl-2-propynyl)acet- aniHde

pyrazolate 4-(2,4-dichlorobenzoyl)-l,3-dimethyl- pyrazol-5-yl-β-toluenesulphonate pyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinone

pyrazosulfuron ethyl S-[3-(4,6-dimethoxypyrimidin-2- ethyl yl)ureadosulfonyl]-l-methylpyrazole- 4-carboxylate

quinclorac 3,7-dichloro-8-quinoline carbox Uc acid

quizalofop (±)-2-[4-[(6-chloro-2-quinoxalinyl)- ethyl oxy]phenoxy]propanoic acid, ethyl ester

secbumeton N-ethyl-6-methoxy-N'-(l-methylpropyl)- 1,3 ,5-triazine-2 ,4-diamine

sethoxydim 2-[l-(eth xyimino)butyl]-5-[2-(ethyl- thio)propyl]-3-hydroxy-2-cyclohexen- 1-one

siduron N-(2-methylcyclohexyl)-N'-phenylurea

simazme 6-chloro-N,N'-diethyl-l,3,5-triazine- 2,4-diamine

SK-233 l-(a,a-dimethylbenzyl)-3-(4-methyl- phenyDurea

Common Npmp hemical Naine sulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)- methyl amino]carbonyl]amino]sulfonyl]- benzoic acid, methyl ester

TCA trichloroacetic acid

tebuthiuron N-[5-(l,l-dimethylethyl)-l,3,4-thiadi- azol-2-yl]-N,N'-dimethylurea

terbaril 5-chloro-3-(l,l-dimethylethyl)-6- methyl-2 ,4( lH,3H)-pyrimidinedione

terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(l,l- dimethylethyl)-6-methylphenyl]- acetamide

terbuthyl- 2-(tert-butylamino)-4-chloro-6-(ethyl- azine amino)-§-triazine

terbutol 2 _τ 6-di-tert-butyl-p-tolyl methylcar- bamate

terbutryn N-(l,l-dimethylethyl)-N'-ethyl-6- (methylthio)-l,3 ,5-triazine- 2,4-diamine

thifensul- 3-[[[[(4-methoxy-6-methyl-l,3,5-triazin- furon 2-yl)amino]carbonyl]amino]sulfonyl]- methyl 2-thiophenecarboxylic acid, methyl ester

thiobencarb S-[(4-chlorophenyl)methyl] diethylc ar- bamothioate

triallate S-(2,3,3-trichloro-2-propenyl) bis(l- methylethyDcarbamothioate

(l-methylethyl)acetamide

Herbicidal properties of the subject compounds were discovered in 35 a number of greenhouse tests. Test procedures and results foUow.

40

TESTA

Seeds of barley ⁽ Hortfc m vulgar e) _f barnyardgrass (EfihjaQsblΩa crus-gaUi). blackgrass (Alopecurus mvosuroides). cheatgrass (Bromus secalinus). chickweed (Stellaria media), cocklebur (Xanthium pensylvani^nmV corn (Zea mays), cotton (Qo^y iy hirsutum). crabgrass (Digitaria spp.), bedstraw (Galium aparine). giant foxtail (Setaria faberii). lambsquarters fChp-n orliiim album), morningglory (Ipomoea hederacea). rape (Brassica napus). rice (Oryza sativa). sorghum (Sorghum bicolor). soybean (Glvcine max), sugar beet (Befra vulgaris). velvetleaf (Abutilon theophrasti). wheat (Trit.i iirη a≤stiyum), wild buckwheat CPolygonnm convolvulus), and wild oat (Avena fatua) and purple nutsedge tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visuaUy evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Table A COMPOUND

Rate (50 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58

POSTEMERGENCE

Barley 9 9 8 8 9 8 9 6 6 3 0 8 5 3 0 0 0 4 2 4 7 8 9 9 6 3 7 8 7

Barnyardgrass 9 9 9 8 9 9 9 2 8 3 3 9 6 1 3 1 3 1 1 6 9 9 - 9 9 9 9 9 9

Bedstraw 8 7 6 6 5 8 9 4 7 9 5 9 7 0 5 0 0 3 2 6 9 10 2 7 8 7 8 9 9

Blackgrass 7 8 7 6 9 10 9 0 3 2 0 4 3 4 2 2 0 3 0 0 9 9 2 9 7 7 8 9 9

Cheatgrass 9 8 7 8 9 8 8 4 5 3 0 6 5 2 3 0 3 5 0 2 9 9 3 9 7 6 7 8 9

Chickweed 9 6 6 9 10 8 10 6 9 - 3 10 10 - 10 0 2 9 4 9 9 10 4 10 10 8 3 10 9

Cocklebur 10 10 - 10 10 9 9 10 9

Corn 10 9 9 9 9 9 9 8 9 9 4 9 9 3 7 1 6 9 7 9 9 9 - 9 9 5 9 9 9

Cotton 10 9 9 8 8 9 9 0 7 9 5 9 9 0 3 0 0 2 0 9 9 9 - 9 9 9 9 9 9

Crabgrass 9 7 1 2 7 8 9 3 0 0 0 3 1 0 0 3 0 0 2 1 3 9 - 9 4 0 0 4 1

Giant foxtail 10 9 7 7 9 9 9 2 4 2 0 8 4 1 0 0 0 3 0 2 9 9 - 9 7 1 3 9 9

Lambsquarters 10 8 10 9 9 9 10 9 9 9 9 - 8 4 7 9 8 2 5 9 10 10 7 10 10 8 7 - 10

Morningglory 9 9 9 9 9 9 9 8 9 8 4 10 9 5 8 6 6 5 7 9 10 10 - 9 10 9 0 9 9

Nutsedge - 2 0 0 0 0 8 - 6 8 0 5 0 0 0 0 - 0 0 0 9 10 - 9 9 - 9 9 10

Rape 10 7 3 8 8 1 9 7 8 8 8 10 10 2 2 0 4 6 0 9 9 10 8 9 9 9 9 9 10

Rice 9 9 9 9 10 9 9 8 8 7 2 9 9 4 3 1 3 9 4 8 9 10 - 9 9 8 9 9 9

Sorghum 10 9 9 9 9 9 9 4 8 2 0 9 4 1 1 0 0 3 1 3 8 9 - 9 9 3 9 9 9

Soybean 9 9 9 5 8 8 9 4 8 7 2 9 9 2 3 0 2 3 2 9 9 9 - 9 9 6 8 9 9

Sugar beet 10 9 8 9 9 9 9 9 10 8 9 10 9 3 9 8 8 9 8 9 10 9 7 9 9 8 7 9 9

Velvetleaf 9 7 8 7 6 8 9 9 9 9 2 9 8 1 7 2 0 1 4 5 9 10 - 9 8 9 9 10 10

Wheat 9 8 7 8 9 8 9 2 3 2 0 8 6 1 1 1 2 3 0 3 7 9 8 9 2 2 3 7 7

Wild buckwheat 10 3 0 6 3 6 8 8 7 9 9 9 9 0 3 2 0 5 2 6 7 10 2 8 8 7 - 8 7

Wild oat 10 9 9 9 9 9 9 3 6 4 0 9 6 1 0 0 0 5 0 3 8 9 8 8 7 0 8 8 7

Table. A COMPOUND

Rate (50 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87

POSTEMERGENCE

Barley 8 7 2 8 9 8 8 6 3 9 0 5 0 0 7 7 4 2 8 6 5 2 9 9 8 8 8 - 4

Barnyardgrass 8 7 5 9 9 9 9 8 9 9 8 9 5 3 9 9 4 1 9 9 7 0 9 9 9 9 4 9 4

Bedstraw 9 10 8 5 8 8 7 8 8 5 7 9 9 6 7 9 8 8 6 8 4 2 6 8 9 8 8 - 3

Blackgrass 8 8 5 9 10 10 9 9 8 7 1 7 5 3 9 9 6 2 9 9 8 3 9 9 10 9 9 - 8

Cheatgrass 9 8 6 9 10 10 9 7 9 9 8 3 2 3 9 9 2 3 9 9 4 2 9 9 10 9 8 - 8

Chickweed 10 10 8 5 10 9 9 0 9 - 9 9 9 - 9 9 10 9 10 9 4 0 9 10 10 9 7 - 2

Cocklebur 10 10 9 9 10 10 9 9 10 9 9 - 9 8 9 9 9 - - - - - - - - - - - -

Corn 9 9 3 0 9 9 9 9 3 9 5 9 9 2 7 9 9 7 5 9 6 2 0 7 9 9 9 1 0

Cotton 9 9 9 9 9 10 9 9 9 9 9 9 9 8 9 9 10 9 9 9 6 2 9 9 9 9 9 9 9

Crabgrass 6 0 0 5 5 9 10 4 2 6 2 6 3 0 4 5 2 0 6 7 0 0 5 7 - 6 3 3 2

Giant foxtail 8 5 0 7 9 9 9 5 5 8 5 8 2 1 9 10 8 6 9 9 7 0 8 9 9 9 3 6 2

Lambsquarters 9 9 7 9 10 10 9 9 10 9 - 9 9 8 9 9 9 8 9 9 8 3 10 10 10 10 9 - 7

Morningglory 9 9 9 9 10 10 9 9 9 9 9 9 10 7 9 10 7 8 9 9 7 5 10 10 10 9 9 10 9

Nutsedge 10 10 9 9 9 10 6 7 9 - 9 9 - 5 8 10 5 0 10 10 0 0 3 9 10 7 0 8 0

Rape 9 9 10 9 10 9 9 8 10 9 9 10 9 7 9 9 9 9 9 9 9 7 9 9 9 9 9 - 8

Rice 9 9 8 9 9 9 9 9 8 9 7 9 8 4 9 9 9 7 9 9 9 8 9 9 9 10 9 9 8

Sorghum 9 9 3 10 9 10 9 8 9 9 3 4 1 2 9 9 3 2 9 9 3 0 9 9 9 9 9 9 8

Soybean 9 9 7 9 9 9 9 8 9 9 9 9 9 1 9 9 8 8 9 9 6 3 9 9 9 9 9 9 6

Sugar beet 9 9 10 9 9 9 9 9 9 10 10 10 10 10 9 9 10 9 10 9 9 7 9 9 9 9 9 - 7

Velvetleaf 9 9 9 9 9 10 9 9 9 9 9 9 9 8 9 9 9 8 9 9 5 0 9 10 10 9 9 9 9

Wheat 7 3 1 9 9 9 9 9 2 6 0 0 0 0 7 7 3 0 8 9 8 2 8 9 9 9 8 - 4

Wild buckwheat 9 9 9 10 9 9 9 8 10 7 7 10 4 0 8 9 7 1 8 9 5 0 9 9 9 9 9 - 7

Wild oat 8 7 0 9 9 9 10 9 3 8 0 2 0 0 9 9 8 2 9 9 9 2 9 8 4 9 9 - 3

Table A COMPOUND

Rate (50 g/ha) 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112

POSTEMERGENCE

Barley 7 8 8 3 3 8 8 9 8 8 8 6 4 7 9 9 9 9 3 9 9 9 9 9 8

Barnyardgrass 9 9 7 0 5 9 9 9 9 8 8 7 7 6 9 9 9 8 4 9 9 9 9 9 9

Bedstraw 8 - 8 8 7 8 9 9 8 7 9 7 7 5 9 9 7 8 7 9 9 9 9 8 9

Blackgrass 8 9 9 9 9 9 9 9 9 9 9 9 9 8 9 9 9 9 5 9 9 9 10 9 9

Cheatgrass 8 9 8 7 9 9 9 9 6 8 9 4 3 6 9 9 9 9 5 9 9 9 9 9 9

Chickweed 10 9 9 10 3 9 9 9 10 9 9 9 9 3 9 10 3 7 2 10 9 10 9 10

Cocklebur _ _ _ _ _ _ _ _ _ _ _ _

Corn 5 9 9 9 0 9 9 9 9 9 9 9 7 0 0 0 0 9 0 9 9 9 9 9 6

Cotton 9 10 9 9 9 9 9 9 10 9 9 9 9 2 8 9 5 8 4 10 9 10 10 10 10

Crabgrass 5 6 6 2 0 8 7 8 5 3 5 2 1 2 3 1 5 7 0 9 9 9 9 8

Giant foxtail 5 8 8 3 0 9 9 9 9 8 9 5 4 3 7 7 7 8 0 9 7 9 10 9 6

Lambsquarters 8 9 9 - 5 9 9 10 9 9 - 8 7 8 9 10 3 8 - 10 10 10 10 10 9

Mo ningglory 10 9 9 9 9 9 10 9 9 9 10 9 9 8 9 9 9 9 8 9 9 8 10 10 9

Nutsedge _{9 9} _ o - - - - - - - - - - 10 8 0 0 0 10 9 9 9 10 9

Rape 9 9 9 9 6 9 9 9 9 9 9 9 9 9 9 9 9 5 7 9 9 9 10 9 8

Rice 9 8 9 9 9 9 9 9 9 -9 9 9, 9 9 10 9 10 9 7 9 10 9 10 9 9

Sorghum 9 9 9 9 9 9 9 9 9 9 9 9 9 5 9 9 9 9 8 9 9 9 9 9 9

Soybean 9 8 9 9 3 9 9 9 9 8 9 9 9 0 3 9 0 2 1 9 9 9 9 9 9

Sugar beet 9 10 9 10 5 10 9 9 9 9 9 9 9 9 9 9 8 9 9 9 9 9 9 9 8

Velvetleaf 10 10 8 9 6 9 9 9 9 8 9 10 9 7 7 9 5 5 2 10 9 10 10 10 10

Wheat 4 4 4 4 1 9 9 9 9 9 9 3 3 6 9 9 9 9 4 9 9 9 9 9 8

Wild buckwheat 7 9 9 9 5 - - - - 9 - 9 9 6 9 - - - - 10 10 10 - - 9

Wild oat 4 2 7 7 0 9 9 9 9 9 9 9 8 6 9 9 9 9 0 9 9 9 9 7 6

o cM in t- t- to o τr to so so m co o o o) H CM t- CM So i m O) O H CM in t- I O 0 ⁾ O in t- fO «3< O O O ⁾ rH SO CO CM CM I so oo

H

00 O H O SO t- O CM CO O OO OO T O I- O OO O CM fO O O I *T 00

I- cM so so ø) θ oo oo σ) SD σ) σ) tn «3< ιn so σ) oo σ) f- ιn oo i r-

00 so i— O) co o) O O) oo oi O) O O) O) t- t- 0) O O) 0i oo r- oo I t- oo rH rH H m tO O) t- O) 0I OO OO 0) O) OI Ol O1 01 O OI O 0I OO t- SD O I CM

00 m fi N oi oi i i— 0) oo o) 0) 0) so oo m eo o) 0) i— i— >o i t—

CO H O so σi eo σi o σj oo σi to o o o so o co σi σi σi i- co r- I I— ω H rH rH rH

CM oo oo 0) O) 0) O) t- 0i oo O) Oi oo so r- r- O) oo O) O) t- i— I oo

00

H o σi cM in t- σi o oo o σi σi m cM øi cM oi σi H r- o so i 00

H o *3 ^, o r- O 0> o> co o o o t- 0) O co o i- I

00 H σ, O O O CM O O O O O O O CM O O O O O O CM O O I CO

I-

CO O O CM CO CM xJ O O O O T CO H O O O O O CM O CM I O 1- O O O CO CM CO O O O O O O O O O O O O O O O I o

O r-

U H so O O O O in O O O O CM SO I O O O O O O CM O O I o

I- m o σι o t- oo «3< CM >o o σι t- σι «ι o o σι σι ιn so o so I τj<

I- o i- H CM t- cM O so cM so in in so o co r- t- xj' in cM O I o t- to to so in oo oo oo cM oo os oo co σi f oo eo σi co co oo t- i- I to

I—

CM cM co cM r- oo r- o tn in o) O) O) so o ^' t- i- in 0) in i- I *τ t-

H o m o i i o i H o r- co i- o o o tO H O so o o o o I- o o o so 0) co eo in m m oo 0) i '* 0i o r- ^ ^, O) 0) ^ ^, M I- H

01 o co so cM O t- I θ "w ιn ι ι- CM θ oι øι o f øι co cM co cM o

. H -srl

O O O O O O O O O O O O O O O O O O O O O I o r to

O O O O O I © © O O O O O O O O O O O O O I o to o O O O O O I O O O O O O O O O O O O O O O I O

Oi CM CM CO t- Ol l— H CO CO 'a' CM t- tO O O I— ^T I- CM O CM I 00 to

00 o cM o co t- m o cM 'a' in cM in H o o m co H CM O o i to » in O) OO 0) O) O) CM 0) OO O) 0) 0) 0) OO O) 0) 0I OO O) CO SO I o o O O in SD I- l- CM CM O O © I I * to in CM CM H t- 00 00 © 0) in in CM OO tO fO CM O t- in t- H OO I 00 t rr oo i— øι øι oι øι r^ oι ø) θ) øι ø) θθ ø) θ) ø) ø) ø) ø) øι θ) to to 0) ^< 0) 01 0) O) CM 0) 0) 0) 0) 0) ι30 0) 0) 0) 0) 0) 0) 00 0) I 01 oo cM ø) co θ) θ) m ø) eo oo t_o θ) to αo θ) ø) ø) θι σι t— co I oo

O O O O O O O O O O O O O O O O O O O O O O O to

O O O O O O O O O O O O O O O O O O O O O I o

O co ϋ cn O O H O O O CM O O O O O O O O O O O O H O I O

O H

O en

00 © O O O O O CM O O O O fO CM O O O O O O O O O O H co r- O O ^T O O O O O O O O CM O O O O O O O O O I o

H co o o o cM o o m o o o o o eo o o o o o o o o o i o

H to in O O O O O O O O O O O O O O O O O O O O O I o

H co

O O O CM CM O O CM SD O O O O O O O O O O O O I O

H en en © o eM H O O co o ^ ^ ^r m o o o o o o o o o i ©

H

© o co-f- in o m T in cM in oi eo co t- o o to so so cM i t

H o «a< © to © I c o o c t σi in iN i c CM 'β' i- t o i co H to

io t- i in

H (M H O 'i' so o o so o ^j' co o o 'S' eM t- o o co o eo I CM CO o CM H O t- 01 I CM CO H CO in O CO O CM Ol CM CM H O OO I 00

CO

Ol σi oo H t— 0) oi t- O) oo o) O) O) so o o) O O) O) O) t- oi I t- CO H H co Q oo oo i— m i— θ) ø) so ø) t— O) 0) o r- i- O ⁾ O ⁾ oo o ⁾ O) in eo i oo

Z CO

D co On, i- © 0 © 0 © 000 © © 000 © 0 © © 0 © © 0 I © g CO O O O SO O O O O O O O O O O O O O O O O O O O O O i o O co m O O O O O I o o o o o o o o o o o o o o o I o co co

O O CM-O O O O O O O O CM O O O O O O O O O I o

CO CO

CO O O O O O O O O O O O CM O O O O O O O O O I o co co

<! (0 O

Φ

H 3

Λ H

(fl H

H S

Table A COMPOUND

Rate (10 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58

POSTEMERGENCE

Barley 9 8 7 7 7 7 8 2 5 2 0 4 2 3 0 0 2 3 0 2 4 5 8 8 2 2 6 7 4

Barnyardgrass 9 7 5 3 3 9 9 0 1 1 0 7 2 0 0 0 0 0 0 2 9 9 9 9 7 7 8 8 8

Bedstraw 8 4 6 4 3 6 7 2 3 2 2 3 2 0 2 0 0 3 0 3 7 9 - 6 7 5 4 7 7

Blackgrass 8 8 4 2 7 8 9 0 0 0 0 2 3 2 3 2 0 0 0 0 9 8 - 8 2 4 4 8 5

Cheatgrass 9 7 7 6 8 5 5 0 0 2 0 2 3 0 3 0 0 2 0 2 9 7 - 7 3 3 5 7 6

Chickweed 9 4 - 8 7 4 9 0 6 8 0 9 9 3 5 0 0 0 0 9 9 9 4 9 10 7 0 7 5

Cocklebur _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ 9 i0 9 l0 9 1 10 9 9

Corn 10 9 3 2 9 8 9 5 7 3 2 9 2 0 1 0 0 5 0 7 8 9 4 8 8 3 8 9 9 Cotton 9 2 3 0 5 9 9 0 0 0 0 1 5 0 0 0 0 0 0 0 9 9 9 9 9 8 9 9 9

Crabgrass 7 2 0 0 5 4 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 4 6 0 0 0 3 0

Giant foxtail 9 8 6 4 8 7 9 0 1 0 0 1 0 0 0 0 0 0 0 0 8 8 7 9 2 0 3 8 6

Lambsquarters 9 - 7 8 5 9 9 3 3 7 7 9 - 0 3 7 7 0 3 3 9 10 6 8 9 5 2 8 -

Morningglory 10 8 8 8 9 9 9 4 5 1 2 6 2 0 5 0 0 0 7 7 9 10 2 9 10 9 0 3 9

Nut sedge 5 - 0 0 0

Rape 10 2 2 5 7

Rice 9 9 9 7 9

Sorghum 10 9 4 3 7

Table A COMPOUND

Rate (10 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87

POSTEMERGENCE

Barley 4 2 0 7 7 5 4 3 1 9 0 5 0 0 3 3 0 0 4 3 2 0 7 7 7 6 3 2 2

Barnyardgrass 6 3 1 8 9 9 7 3 8 9 3 9 0 0 5 7 0 0 6 9 0 0 8 9 9 3 0 8 2

Bedstraw 8 8 - 2 8 7 4 7 5 3 7 7 6 0 5 7 4 5 4 7 0 0 3 6 9 7 7 7 0

Blackgrass 5 5 0 7 9 9 8 4 3 1 0 2 0 0 2 4 5 0 5 8 5 0 9 9 9 9 8 9 4

Cheatgrass 7 7 - 9 10 9 6 3 6 7 7 0 0 0 8 8 0 0 8 9 0 0 9 9 9 6 4 8 4

Chickweed 10 9 2 0 6 8 5 0 4 - - - - - 5 7 8 3 - 9 0 0 4 9 10 9 3 3 2

Cocklebur 10 10 9 5 9 9 7 7 9 9 6 9 9 2 - 9 9 7 9 9 0 - - - - - - - -

Corn 8 5 0 0 7 9 9 7 0 9 2 9 7 0 3 7 6 2 0 7 1 1 0 1 5 7 7 0 0

Cotton 10 9 9 7 9 9 6 4 7 9 6 9 9 2 6 9 5 5 7 9 2 0 8 9 9 8 7 8 6

Crabgrass 1 0 0 3 8 3 2 0 0 3 0 1 0 0 0 1 0 0 1 3 0 0 1 5 5 4 3 2 0

Giant foxtail 2 0 0 6 9 8 7 0 4 4 3 3 2 0 7 9 5 0 7 9 3 0 6 9 7 4 0 4 0

Lambsquarters 9 9 3 9 10 9 7 5 9 8 9 10 7 7 8 9 9 2 9 9 5 0 9 9 - 9 9 8 1

Morningglory 9 10 8 7 9 10 8 6 9 10 9 9 10 2 9 9 0 1 9 9 2 0 9 9 9 9 8 9 9

Nutsedge 9 8 9 6 8 9 0 0 7 - - 0 0 5 0 9 - 0 - 5 0 0 0 - - 0 0 - 0

Rape 9 9 9 9 9 9 7 5 6 8 8 9 8 5 9 8 8 8 9 9 7 0 9 9 9 9 5 8 8

Rice 9 9 6 9 8 9 9 9 4 8 4 8 5 0 7 8 1 0 9 9 9 0 9 9 9 9 9 9 3

Sorghum 7 6 2 9 9 9 8 4 9 9 1 3 0 0 5 8 0 0 7 9 0 0 9 9 9 9 9 9 5

Soybean 9 9 3 9 9 9 9 7 7 5 8 9 9 1 8 8 6 3 8 9 1 0 8 8 9 7 8 7 0

Sugar beet 9 9 9 8 9 9 6 4 7 9 9 10 10 9 9 9 8 9 - 9 5 2 8 9 10 9 9 9 0

Velvetleaf 9 9 9 9 9 9 6 4 9 9 9 9 9 5 6 8 7 6 7 9 0 0 9 10 10 8 6 8 5

Wheat 2 2 0 8 7 4 8 5 0 2 0 0 0 0 1 0 0 0 5 3 2 0 8 6 5 5 3 0 0

Wild buckwheat 9 8 0 10 7 8 8 5 7 2 7 6 2 0 0 8 2 0 4 9 0 0 7 7 7 8 - 7 3

Wild oat 4 2 0 8 7 4 8 5 0 5 0 0 0 0 6 3 7 0 7 6 2 0 8 5 3 7 5 0 0

<x> o σi oo o ^r to t— σi σi O T øi øi t- oo σi r- eo so eo o oo o i- øi σi oo σi o o t- σi σi cM oo o σi σi σi σi øi σi i— σi oo o σi so rH rH rH H

SO oi σi ϊ— oo oi co oi oi oi ^ r— 0) <_D r— 00 0) 0) 0) 0 0) 0) 1— σi SO H in ι^ oo co oo oo ιn oo σι ι- ιn f- σι ιn to t- σι oo σι t- σι co ι— t- O cM *r t- σι t- co σι © σι © © r- σι σι σι σι σι σι r- σι o I CM cM o øi σ c- t- σi oo σi o cM o σi f- σi σi oo σi σi oo co I *r

© t— t 00 01 0) 0) 0) S 0) H SO O) 0) 0) 0) O) 0) 0) 0) 0) C0 I O) m

H σi CO 0) O) O) O) O O OO 0) O 0) O O 0) 01 0) 0 ⁾ O ⁾ 0) O 0) 1 t— fl< rH rH rH H H

00 i— 0) oo 0i 0) O) o i o) o o o o) 0) 0) 0> 0i 0) O 0) i m

H rH rH H t- t- 0 ⁾ t- 0l 0 ⁾ t- 01 O OI O CM 0 ⁾ O 0) 0) O) 0 ⁾ O) i O t- I oo

H H

SO in so t- øi oo co o cM øi o cM oo σi σi σi σi σi oo σi σi co i in "3" H in fO O CO OO CO O I— O OO O O OO OI O Φ øl f— CO OI CO ^* I 00

"3 ¹ I— CM C— σi io so σi co co o so oo σi σi σi σi σi σi σi io σi I 0)

S co CO 01 I— 0 ⁾ 01 O O 01 01 CO CO O 0l 01 t__O 01 O1 0l 01 O t__ I CO O "* rH rH H

O H CM r- σι t- σι t— so o) oo oi co in o so 0) 0) O) Oi co 0i 0i i_— I so

H r- so m co r- m 0i o co o cM t- H oo co o) O) 0) t- 0) So ι t— o so t- so øi σi m t— so σi cM t- oo oi in o oo oo oo oo oo i— l t- σi in to t- co co o cM co r- o cM co σi o o σi 'ϊ σi eo σi so I co to co oo t- oo 0) 0) r- t- so oi co t- oo o oi o 0i 0i oo 0i oo oo I ø) co H H

I— m oo i- t- oo ^r so i— 0) CM ^J ^, in oi so to 0i o so 0) «o t- I oo CO so CM ^r oi o co o io co so o cM in t- i co oo co σi t- t- co i to t

H in co r- oo f- t- m oo co σι θ to «3 ^, σi "S ^< © øι σι eo oι so co I σi co

H

CM CM SO CO O CM O O SO tr O CM CO ^r O OO t— O T oo m o øi o CM CM

O CM CO CO O O O CO O O O CM © I co co T in ^r o o co o

CM CM

O H co co oo in to I σi cM O ^r σi co o σi σi co σi co cM σi o cM CM CM ø) co σι so in m r- i co σi o m σi σi σi oo σi cM co σi σi to σi σi H CM oo <t_r eo so to co in I oo en cM so σi σi t— r- σi so co o σi — ' r- σi

CM

I— σi σi m σi co o l σi so co t— oi σi t— o oi oi io oi oi oi βi o

H CM

IO co co in σ> co o i eo so o i— oi oi o o oi oi to co co oi cM Oi en eo en

"* t- CM øi co ø o 1 ø) o o to o oi i o σi σi σi σi io so oi σi

H rH r-i rH r-l CM

CO I— 0) 0) 0) O) O O 01 © CM OO O1 O 01 O 0) 0) OI O 0) OO 0) 0) H rH rH rH rH H CM

CM oi 0) 0) 0) 0) t- e) O O in 0) 0) O) O 0) O) O 0) a_) O) 0> oo o H H rH r rH H CM

O) O) 0) 0) 0) ^ι I O) 01 C 0I 0) O CM OO 0) 0) 0) I— 0) CO SD 01 t- ø) t— f- σi oM o σi i— co t— σi σi ι m m βi ω o σi cn co o) oo o co oo i- o I CM θ CM CM co m o o øι «a' o o o t- o r- 00 00 0 ⁾ 00 0) 0) 0) I 0 ⁾ 0 ⁾ 10 0 ⁾ 0 0 ⁾ 01 01 01 01 10 0 01 01 01 01

©

CM t- 01 0) 0) 0) 1— øi i øi oo p- o r— oi N oi oi o oi o oi o oi oi o H rH r.

CM so 0) 01 01 0) 0) 01 I 0 0! 0I 0 0 0) ^' 0! 0) O C0 0 0) 0) 0) 0 o rH r-i rH rH τ-i rH

CM m 0) O1 O) O) O O) OO O 0) OI O O O O 01 0I O 0I 0) 0) OI 0| O1 o H H H H H H H

CM

0) 0) 00 0) 0) 01 I 0) 00 01 0) 0 0 01 0 0) 0) 0) 0 0) 0 00 0) o rH ri rl t-i H

CM

CO 01 01 00 0) 01 0) 00 0) 00 0) 10 0) 0) I 0) 01 0) 0) 0) 00 0 01 0) o

CM

CM oo e f-"'σ) t- «o ^' øι oo oo σ) t- σ) <o ιn σ) σι σι oo o>ι oo i σι 01 co so i- r- m o t- so j- o so oi oo co m oi so t— t- m m i t-

O) H

A

- a co H CO (β O •H H ι Φ CO (0 Φ U

^l S co co A A O 4-> <H tn to cn O m - M H Φ O O 0, O S (fl (fl φ 3 w o to tn Φ Φ Φ ϋ A

"5 . (0 φ XI ca <H ? tn tn g C Λ H 3 (0

>ι rt tn tn s Φ C w a n 3 (fl 4J A 0

Φ . w O , Λ! 4-1 X H O & ⁾ 4-1 CO -rl φ A Φ Φ 4->

H Φ E-i H C cn θ tU θ *. C 4J _Q C C co φ φ &ι J (lJ > cβ ^, O O

Λ 4-i W "O (fl Φ -H O 4J (0 t0 >H 4-l ft O M > tD H Φ H H

⁽ 0 ⁽ 0 O tfl tβ Φ H Λ Λ O O O -H O 3 ( (00 --.HH. O O 3 Φ Λ -H -H fn m w m u u o o o o u μi s z 0- 0, w w co > S S S

so co in r— σi eo «3< r— σi co o oo I en ι so σi σ σi m eo t- oo oo so

CM in t— t- t- oo oo ^ t— σi m o oo σi σi m σi σi σi co oo oo m i— so

CM so so t- t- t— © tr eo CM co *tr t— σi o in co co m o eo co co t-

SO CM co in co in cM ^ in H i— ØI O CM CO ØI I σi σi σi σi r- σi m T io so

CM CM in to so oo oo o i- H O i— i— σi i i- i— i— co in co co σi t- so

CM H co oi r- o oi so oo oi T in oi r- o I oo σi σi oo so r- σi oo σi o

CM o oo i— t- oi m H Oi cM f- oo I co o t- o σi σi m r- eo oo σi o H

CM ø) øi r- i— σi t- σi co oo o) oo 0) 0) 0) CM O) ^_f< co 0i o o o) r— θ) øι øι ι— oi oo oo cn m H H

CM m t— oi oi βi n oi oi oi oi I σi σi σi rø ir σi co tn σ) cM CM t- t- in o o H in o o in t- I i— co co cM o m o t- cM

T CM I— i— so σi t— σi o cM o σi I øi σi co σi co cM CM σi t- ιn co t- r- ι— oo t- σi eo cM so i σi ι σi σi σi øi σi σi co σi i- r— i— i— øi øi in oo σi oo m co I σi o σi σi σi σi co co r- o m in σi r- σi cD cM cn oo co r- σi fO t- σi σi σi m w oo i m m

CM o n <r i- i— so o o co CM o ^i* I in o in co CD so I in r in in m

CM

0) SO SO t- I CO I— I OO 0) SO SO O 0) I OO Ol I- t- OO CO ^_r | SD

00 co so c- co *a* σi I σi ø) ι t- o σi 'q' oo σi σi t- eo oi t- I r-

H CM I— ø) co c- σ) oo t- I i— o oo σi σi σi σi m σi σi so σi oo t- i co

H CM SO t- so m t— so i i oi oi m u oi I- I ιn oι <j H oo < i oι ιn CM in o) oi o o) ø) tn i ø) ø) i 0) 0 0 0 0) 0) 0) ^* 0) 0) 0) 0) 0)

CM

co co O w o o, τ> S tfl tfl Φ 3

H ω rt Φ X)

— S ! ι (fl w cn tn * Φ φ -

H Φ EH H C co υ io o ! C 4-ι _ t ja 4-l C M U 'U t0 Φ -H O 4J t0 tfl g M 4-i α θ W >ι tn H Φ H H tfl t0 θ t0 lfl Φ H Λ Λ θ θ θ M H (fl θ 3 (fl -ri O O 3 φ _C -H -H

H « <j o, α, m ι- α υ o u u υ ci) ι-q S ι_ -; c w w s s s

Table A COMPOUND

Rate (10 g/ha) 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310

POSTEMERGENCE

Barley 9 7 9 4 8 2 2 6 3 2 4 9 8 9 7 5 8 6 8 7 5 7

Barnyardgrass 9 6 9 5 9 2 2 4 3 1 0 9 9 9 8 3 9 2 8 2 8 9

Bedstraw 7 3 . 5 3 4 3 2 3 5 0 0 7 5 7 3 5 6 6 6 6 6 6

Blackgrass 9 9 9 6 8 4 7 4 7 4 4 9 9 7 5 3 9 8 9 7 7 7

Cheatgrass 9 8 9 4 7 2 5 2 2 0 0 9 8 9 8 0 7 3 7 5 7 6

Chickweed 9 2 7 7 3 3 3 3 7 2 0 7 7 9 9 6 6 7 2 2 0 2

Cocklebur _ _ _ _ _ _ _ _ _ _ - _ _ - _ _ - - 5 i 8 9

Corn 9 6 9 6 9 2 1 2 2 2 0 5 9 9 1 0 8 6 7 6 8 9

Cotton 8 7 8 6 7 1 7 3 7 4 0 9 9 9 9 6 9 8 6 9 9 9

Crabgrass 7 2 9 2 5 1 1 1 0 0 0 5 7 8 5 4 7 2 4 2 6 0

Giant foxtail 9 6 9 6 8 3 3 4 3 3 2 8 9 9 3 2 9 3 7 3 7 6

Lambsquarters 9 7 10 7 8 5 8 7 9 5 5 9 9 - - - - 4 - 8 8 9

Morningglory 9 6 9 6 5 6 3 2 2 2 1 5 9 9 8 3 9 3 6 3 9 10

Nutsedge 4 0 - 0 0 0 0 0 0 - 0 - 5 7 0 0 0 - 4 3 3 7

Rape 0 8 9 9 7 0 3 5 5 0 0 8 9 9 9 7 7 0 7 6 7 -9

Rice 9 8 9 8 7 2 8 6 7 3 0 9 9 9 3 0 9 8 9 6 9 9

Sorghum 9 7 9 8 9 2 2 3 6 3 0 9 9 9 8 3 9 8 8 4 6 8

Soybean 9 2 6 1 6 1 4 2 4 2 0 7 8 7 1 0 8 2 8 8 8 9

Sugar beet 8 7 9 9 5 3 2 7 8 2 3 8 8 9 8 5 8 2 5 6 7 8

Velvetleaf 6 6 9 7 5 3 6 1 0 0 0 7 8 8 7 1 6 3 7 5 6 9

Wheat 9 7 9 5 3 0 1 3 2 0 2 9 9 9 3 1 7 0 5 3 7 4

Wild buckwheat 8 6 9 7 8 3 0 3 6 0 2 8 7 7 8 7 7 6 7 2 5 7

Wild oat 9 8 9 5 7 2 2 5 3 3 1 8 8 8 5 2 7 5 8 2 6 9

O O O O O O O O O O O O O O O O O O O O O I o to

O O O O O O O O O O O O O O O O O O O O O I o to to o o o o o o o o o o o o to o o o o o o o o o I o

CO to 0) T H in tO CD CM H OI CO CM l- CO H O O Ol CO OI in O l- I 00

CM CO

00 CM o m o i- o o -c cM o in H H o o co H cM co o o I r- CM CO

I— I— CO O) CO CO O) OO 0) 0) CO O) O) 0) _— O) O) 0) OO 0) CO H I CM CM CO

SO CO O SO rJ ⁱ m so O H O O O CO H O CO O) H . CM f- O 00 I if CM to m m n* so m ι- ι— o σi øi cM i- m oo I σ) σ) σ> oo co o σ> ι øi

CM t u< θ) øι θ) oo θ) ø) ø) ø) ø) m ø) ø) θ co ø) ø) øι øι øι θ) ø) i ø) CM H O

CO øl SO C— 0) 0) 0) 00 0) 0) 00 0) I O OO OI 01 0) 0) 0) 0 0) I 0) CM CO

CM σi to so t— σi co σi øi σi t— co o m m oi O) O) eo o) 0) O) ι σi CM CO

O O O O O O O O O O O O O O O O O O O O O I O to g o O O O O O O CM O O O O O CM I o o o o o o © I o CM

O to S 0) O O O O O O H O O O O O H O CM O O O CM O O I O

O H U O oo O O O O O O t- O O O O O H' O U' U' O O CO O H I H

H to » O O CM O O O O O O O O O O I CM CMO O CM O O I O

H to so o o o o o o o o o o o m o o o cM o o o o o I o

H t m O O O O O O O O O O O O O O O O O O O O O I o

H O n ¹ O CM IO CM O O O O O O O O I- O CM U' CO O CO O O CM O

H O to m CM CO CM CO O O O CM O CM CO H O CO P- CO CM in o CO O CO

H to

CM to σi t- oo eo o r- r- r- o in i σi f t- t- co m i co co i m H CO t- OI SO 0) OO © 0) l- 0 ⁾ fO SO © O ⁾ CM I— OI OI OI OO CM ^ OI OO

H H CO

^' a tn

A C_> W

^ Z tfl tn a tn tn

O tn to co O M

O P, T3 S ro (fl Φ 3 rii H H M (fl M l-i φ £}

^ 2 ι Λ M tn tn ϊ Φ Φ m o >t *J . H Φ EH H C co υ ta υ ^ 4-) _ _

_Q 4J W O tβ Φ -rl ϋ l-l +J lfl Cfl g 4J C_ 0 (H l>ι tn H Φ H H Λ « O (fl (0 Φ H _! J-! O O O -H (3 Q 3 (fl ->i O O 3 Φ Λ -rl -H

CO CO CO t— 00 00 0 ⁾ O ⁾ 0 ⁾ t— OO O 0 ⁾ m O ⁾ 0I O IO O) CO OO I CO f H H to

0 ⁾ tO ιf ø ⁾ t- O O SO O CM CO CM CO H m 0 ⁾ SO H t0 0 0) I 0) if to o 0 ⁾ SO CM Ol O ⁾ in H 0 ⁾ O H I"- CM CM O OO O ⁾ OI CM H H 0l I 0) if to

01 σι ø) ø) ø) øι o © σι o t— o o ø) co ø! ø) ø) ø) o o ø) I ø) ro to

B OO 0) 0) t— 0) 0) 0) 0 0) 0) 1— 01 0 0) 00 01 01 01 0) 0) 0) 0) I 0) CO H H

O co t- O O O O O O O O O O O O O O O O O O O O O I o O co

U O so O O O O O O O O O O O O O O O O O O O O O I o

CO CO m O O O O O O O O O O O O O O O O O O O O O I o

O O O O O O O O O O O O O O O O O O O O O I o to

O O O O O O O O O O O O O O O O O O O O O I o

Φ

H ^, ti

A H

- -rl

H S

Table A COMPOUND

Rate (10 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58

PREEMERGENCE

Barley 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 3 0 0 3 0 2

Barnyardgrass 4 2 0 0 0 1 3 0 1 0 0 0 0 0 0 0 0 0 0 0 9 9 5 9 2 7 3 9 8

Bedstraw 4 0 2, 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 1 8 0 5 8 2 4 7 2

Blackgrass 2 3 0 0 0 4 0 0 0 0 2 0 1 2 0 2 1 2 0 1 7 6 0 8 2 0 3 8 4

Cheatgrass 7 3 0 0 3 9 6 0 0 2 3 2 2 0 0 3 2 2 0 2 7 7 0 6 0 0 4 8 6

Chickweed 9 0 0 0 2 6 6 0 3 0 0 - 0 0 0 5 0 0 0 - - 9 3 9 10 10 0 9 8

Cocklebur _ _ _ _ _ _ _ _ _ _ _ _ _ _ - _ _ - _ _ 4 9 ₇ 5 ₉ 4 0 2 1

Corn 8 2 1 0 2 8 6 0 0 0 0 0 0 0 0 0 0 0 0 0 5 7 0 8 5 0 1 9 7

Cotton 3 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 6 9 0 8 3 0 0 6 2

Crabgrass 9 5 0 0 0 2 7 0 0 0 0 0 0 0 0 0 0 0 0 0 4 9 3 5 2 0 0 1 0

Giant foxtail 9 4 0 0 0 2 6 0 0 0 0 0 0 0 0 0 0 0 0 0 6 7 2 7 0 0 0 7 2

Lambsquarters 8 9 2 0 0 7 9 0 0 9 - 3 0 0 0 0 0 0 0 0 7 9 7 9 8 - 6 8 5

Morningglory 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 9 2 3 9 3 0 0 0

Nutsedge 7 0 - 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 9 9 - 5 0 0 0 - 5

Rape 0 0 0 0 2 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 7 9 2 8 8 8 5 9 8

Rice 9 4 0 0 3 8 8 2 2 0 0 2 0 0 0 0 0 0 0 0 9 10 8 9 9 7 5 8 8

Sorghum 2 2 0 0 0 5 7 0 0 0 0 0 0 0 0 0 0 0 0 0 5 5 2 2 2 1 1 6 1

Soybean 7 2 0 0 1 2 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 7 7 0 0 5 3

Sugar beet 8 2 3 2 4 8 9 0 2 2 0 0 2 0 0 0 0 0 0 0 7 9 5 8 9 7 6 7 7

Velvetleaf 2 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 2 8 2 6 0 0 0 5 1

Wheat 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 4 0 0 2 2 0

Wild buckwheat 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 3 7 0 2 4 2

Wild oat 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 5 0 5 2 0 2 3 3

P O O tO CM O O O O O O O O O O CO O O O CM O O tO CM to o o cM to o ro co o o o o m o o cM o o o r- o o m o t o o in cM CM in o ro o o o σi o r j' o o o co o o to cM

O O O CM tO CO O O O CM O I- O CM iT O O O r m O ir CM o O O O CM CM CO O O O O O øl O O l— o o o m o o cM O

© o o o o o o o o o o m o o o o o o cM o o co o

00 O O O CM O O O O O O O O O O CM O O O U O O O O

O O O O O O CM O O O O I O O O O O O t- O O CM O

IO CM O O U' CM CO CO CM H CO CM CM CM O m n' CM O CO O O O CM m o cM i if co H o o o o m o o fo o o o r- o o i CM

CM

H o o so t- co co o eo o o i o o t- cM o o m o co m u' u ^, u ^, o o cM o o m o o H CM O o eo o o o m f- σi i øι vo cM H σ) co to to σι σι r- co cM θ co co t- oo i t- co co cM ø) θ) oo co eo t- f- oo m to m m o o — ' H m r- co i i- to io cM Oi oi oo co o in co co so o H CM ø) u< σ> CM t- r- σi i oo oo σi co o eo cM Oi σi oo co σi t- i- co m

CO O O O O CM CM I O O O O r- H O O O O O CM O O O O t- o cM in cM co σi σi o co eM o o σi co so m H to ω cM O fo o

H H

H so © co r- to r- m i m oo m o oi σi so r- t- ni it co i- o co o

H H O H CM in r- c i m o o o o o co o co so cM in cM O O CM

H H

H i o co t- so r- i eo to o cM Oi H O t- r- r cM in ro o H CM

H H to o <N m <f lo o i H O O © i O O CO H O O CM O O O O

co H (0 (fl

A W •rl 1 Φ ^ U tfl Φ u A t z co co A A 0 ~ w tn tn tn O U W M i-l H Φ (fl X o ca ^■ 0 » tfl Φ 3 to o (fl tn Φ § Φ Φ O 4-1

Hi H ι_ w (fl n Φ Λ ea <μ 3 tn tn C Λ H 3 ⁽ fl ι to M tn cn * Φ a μ σ σ ¹ cc ΌΌ ⁽ fl 4J

Φ 2 0) >, 4-1 x x H o XI O _ e .n .-ι co H . Φ_ _C Φ Φ 4J

H II U H n υ ⁽ fl υ __ 4-ι _) C A C n Φ t A (d > π) 'α O

W lH O (fl Φ -H O 4J (fl (fl B 4-l (_ υ >ι tn H Φ H H

(0 tβ 2 ^{' '} 4) rH A A O O O ^' - ^' t _m O ^{' '} - ^' 0 0 ^' <V A - - -rl in α α» i, oi _, _i) U u u u u u t!i _ S 2 « « n n oi s $ s

co O O O tO m O OO O O O O OO CO O O SO O O O H O O O

I— o m to m i— ø) o o o o m ø) CM θ o oo o H to o o cM θ o

H so o o o u f— σi o ir o o o σi cM O O in o cM cM co cM CM O o m cM o σ σi o o I © o o co o cM o øi so o o σi o m o σ so H rH H H

CM o o i— i— co t- O H O o o m π o m oi CM CM m o o I o m

O O I CM CM T H CM O O O O iT O O m o m CM O O i o o o o m o oo t- H CM o o o r- m o H t- © ιr ι— o co ι o m

H

01 m m co m o oo H m t- o o co to t- co σi co so co co ui i CM T oo H U< I— >* co co o ^ ^, © o cM O) o o) p- ao cM co eo o so I CM u< r- H CM CM CO CO I H O O O O I- O iT H OI O m sO O CM I m T H

O ⁱ r t- m cO I- H H CM O CM t- CM O I- O I ⁱ m oO CM CM I o T H H m o o m cM O 1 H CM I o o o o o o co cM to o o o i o u< CM H i- t- cM i- cM so cM co o cM so m øi m io to cM co i m u< s co co r- m r- co r- r- oo so to oo oo so o) Oi O) m 0i co so m i CM

O u" α H

^ ^• ^• r- so σi r- in so in in so oo co co i- σi so co oi co t- i

CM O O CM f- O CM O CM O O m O V C t- CM CM CO O U' I SO o o o o m r- t- o o o o o r- o o o o o o i- cM CM I CM

O) © O CM CM OO O O O O O O OO CM O O O O O f- O O I o ro

H oo CM CM CM SO OO m cM O CM O O IO H O O t- O CM r- O CM I m co

H r- CM O fO CM t- SO O O O O O O O O CM H O t- O CO O CM ro o o o co r- i o o o o o m H o o o o o r- cM CM i ^■ * m o o * co f- ^' O H o o o o o o fo ir o t- o cM i to

3 ffl

Φ Λ Φ M Φ 4-1 ___

H Φ Φ tn Λ ⁽ fl ⁽ fl O O Λ P- O W >ι tn H Φ H H Cβ ⁽ fl -H θ 0 3 Φ 4-! -H -H

H « α c ι - 2 _2 3:

CM O O O O O O I O O O O O O O O O O O O O O O © CM CM

O O O O O O I O O O O I o o o o o o o o o o o

CM

CM

O O O O O CM O O O O O O O O O O O O O O O O O © σi O O CM O t- t— O O O O O CM O O O O O O O O O H CM

H

CM H CM t- 0 ⁾ I O O CM CM OI O O H O O O CM O H H CM

H H CM * in ιn I O O CM CM tO O CM CM O O O CM H O I— tO

O O O O CM U" I O O O O SO O O O O O O CM O O O CM in O CO CM CM m øl I O O O O øl O O H CM O O m CO O CM CM

H

"* H O CM CO 00 01 I CM t- H H Ol CM CO lO CO O t- CO O H 'a' CM H CM

CO H u ⁱ m cM σi øi o σi o so cM cn to o co cΛ cM r- cn c— H CM CM H CM

CM H CO CO OO CD I O SO CM CM lT OO CM O m m CO CM CM H SO CO CO

CM o so cM in co σi I co to so co σi o o t— so cM so co m oo rH io

O CM H CO SO t- O O O CM CM CO O O O O CM CM CM O CM CM CM

O CM

O O O O O O O O O O O O O O O O O O O O O O O

O o υ CM

00 so t- ro t- oo m cM oo "β ^, sD oo m so oo σι σι σ) ij' i- CM So c4 m o

CM r- H H I— r- r- t- βs to iM ^' CM m iN O H co to m H CM so co r- o CM

SO CM ir t- r- co co © oo fθ co t— oi t- I H øi so r- so in f- o t— O H CM in θ) ø) t— t- o) 0) o r- m o) 0i i (- o oo co co m co so oo m co o H H

CM f H* CM © tO f- I— I OI H OI β Ol f Pl OK fl in i' OO O in o

CM t cM CM o m co m i in o in o m cM in o oo cM u' CM O ii' fO in o

CM

CM o o o m o m o so o ^ so cM o o o ^ o co o o o I co 0) H

H O O O O O O O O O O O O O O O O O O O O O I o

0)

Φ

H Φ !

Λ θ _< o μ ι t H Φ H H

(0 (0 -H O θ 3 Φ J-! -H τl

En κ α n w n > ϊ ϊ ϊ

f CM m m m so σi ι co so cn io σi ro cM so r- i- co oo io so co to IT CM O cN so r- cn t- ø) i σ> CM σ> so σ> ιn co r- σ> oo ιn _- ι- τ co co CM

CM so so ^ m t- oi i so m σi co σi m t- so co fo u' co so m i— so T CM

H m co to i- co σi i σι cM σι σι σι u ^, σι ιn σι oo ιn tn cM so cM so T CM o i— CM i— co m i σi r σi i— m so m u< σι σι ι— <τ <» eo to IO

IT CM

0) o o o to o o i o o o o o o o o o o o o o o o o CO CM

00 o o cM CM o o i o o o o o o i o o o o o o o o o CO CM

I- o o o o o o i o o o o o o o o o o o o o o o © fO CM so O O O O O O I O O O O O H I o o o o o o o o o

CO CM m O O O O O O I o o o o o o o o o o o o o o o © O CM 3* O O CM O O O I O O O O O O O O O O O H O O CM O co

CM CO O O CM CM U" O I O I O O O H I O O O O O O CO O CM to

CM

§ CM O O O O I- O I CM O O O CM H O O CO CM CM O O CM O U" to

O CM

O H O O I- CO I SO CM H ^, CM CO © in θ U ^, ι* SO O H ll ^, CM CM

O co

U CM o O O O CM I- C4 I H I O O CO H O O fO H CM O H O O CM O CM

0) I H I I I I I CM O O H I CM O I H CM fO I H I I I CM CM

00 O O O f C- O I O O CM H iT O I O O CM O O O O O CM CM CM

I- O O O O O O I O O O O I O O O O O O O O O O O CM CM

SO O O O O O * I O O O O I O O O O O O O O O O O CM CM in O O O O O O O O O O O I O O O CO O CM O O O O O

CM CM u< O O H O O in O O O CM CM O O O H O O CM fO CM O O O CM CM O O O O O O t- I O O O O f- O O CM O O O O O O CO O CM CM

Φ rt! tn τ)

Φ Φ H co φ Φ

A 4-i i-. o ι t H Φ H H (0 3 fβ -rj O O 3 Φ _C -H -H EH z α ^β, c w co s :s s

oo CM O ir cM co oo in cM So in in oD tn co so to i— cM f- so o cM CM

CO CM r- H CM O CM 01 1 CM CM OO ⁽ O 01 CO O 0 ⁾ CN O CO OO CM O CM

00 CM so H to ir T i— co so to cM oo to fo m I eo cM m o m to o o cM O CM in o o H H m co «q ^, o o m tO 0) H o sD o o o r to o H O

CO CM

IT rH CM ( m <» O ⁾ m CO H r CO 0 ⁾ CO CM CO CO fO rH CO r CM m CM co

CM

(O ro o o so oo co r m cM m cM I to o co m to u< ι— r co «* CM 00 CM

CM O O O O O O O O O O O I © O O O O O fO O O I o CO CM

O O O H O O O O O O O O O O O O O O O O O I O

CO CM o o o o o o o I o o o o o o o o o o o o o o i o

00 CM øi O O O O O I O O O O O O O O O O O O H O O I o

I— CM O o o o o o o o o o o o I O O O O O O O O O I o I- CM

I- O O O O O O O O O O O O O O O O O O O O O I o I- CM

Z so O O O O O O O O O O O I O O O O O O O O O I o O t- O CM

∑ (- oo cM co eo co o oo so ø) ø) i' co o cM θ) ø) m cM θ t- o so

3 r-

U CM u ^« O O O CM in O O CM CM O O O O O O fO CM O O O O O CM t-

CM CO O O O CM t- O O H O CM H O O O O m H H O O CM O CM t-

CM

CM H CM CM m co co o cM co eo σi σi iN o o σi H H fO o o o fo r-

CM

O H H rn oo io o o cM n' o m fo o o m cM o i o co so co r-

CM o o o o t- σi o o H CM m o i o co o m cM CM O o r m m t-

CM

0) o o o o m o o o o o o to o o o o o o o o o o o so CM oo o o o co σi oi o H Co o o in co o H co fo cM H O O O in

SO CM

I— o cM O co co o o m cM o o I o o H in in in ro H co o co SO CM

A (0 0 τ) H -H κ

O O O O O I O O O O O O O O O O O O O O O I O t to

O O O O O I O O O O O O O O O O O O O O O I o to to o O O O O O O O O O O O O O O O O O O O O O I o to

0) O H O O rO CM O CM CM O O CO O O O CO CM CM O O O I CM co O H O O O O O CM CM CM O O O O O O O O O O O I O to

I- cM o m m r- σi H σi m m so σi ti r- σi σi co r σi H O i CM to so O O O O O CM O O O O O CM H O O CO O O fO O O I CM ro o o o m t- oo o i H o o fO H i o co co cM in o cM i ro t fO m t- OI 0) H O) CO SO CO 0) tO O) 0) O) CO 0) OO CO SO I IO to co H oo co 0) 0! O co in r- co 0) in fO 0 ⁾ O) co O ⁾ oo to oo I co

CM to cM H H t- σι ø) o σ> CM in ro σι cM in r- ø) eo ι- σι ιn ιn i t—

O O O O O O O O O O O O O O O O O O O O O O O to

§ o O O O O O O O O O O O O O O O O O O O O O I o

O en

S ø) O O O O O O O O O O O O O O O O O O O O O I o

8 H υ to

O O O O O O O O O O O O O O O O O O O O O i o

O O CM O O O O O O O O O O O O O O O O O O I o so o o o o o o o o o o o o o o o o o o o o o o o

H to m O O O O O O O O O O O O O O O O O O O O O I o

H to

O O O H O O O O O O O O O O O O O O O O O I O

H to fO O O O H O O I O O O O I O O O O O O O O O I O H to

O O O H CO O CM O I O CM in rO O O O O CM fO CO O I o

O O O O O O CO O CM O CM O in O O O O CO O CM O I o to

4J co H co eg co ^• H μ ι φ α) ra Φ μ A μ co o 4-> 4-> o 4J IH tn co co O μ to w μ H φ - V * CO ⁽ fl Φ 3 co o S tn Φ 0 A μ fo M μ <u Λ d H-ι a, tn t 9 (I) ι ra μ tn tn * Φ _ r μ. _ σ _ c Ό „ 3 (0 *J Λ O

0) , 4-> __ -P >! H o _ »t.n. —4-t eo .H _C Φ μ φ 4J __ rH G in o ea o X G A A - G ^{J "} C co tnΛ (β !> (β τ3 τ3 μ μ O tβ Φ -H υ μ -< ro (θ μ 4_ Λ O μ >ι gin Φ H H

Λ to Φ H A A o o o M -ri B δ _ ?t -H δ o" 5 i - -H ca _-j « m u u u u u u j) ^ S 2 oαs α-! OTOT OT OT > i_e s 3:

CM cM θ o o co [- CM 3 ^, CM to co øι u ^, o ιn co σι co r- cN in i ^■ * u< co

O O O CM CO O O O I O O O O O O O O O O O O I o o o o o r- i O O O O O O O O O CO O O O O CM I CM ι? co

01 co r o in σi σi iø i— lø σi σi σi cM Φ øi βi øi in αi in co i CM co to

§ 00 m cM CM o σi oi cM oo n' CM in oo m so m i- H so cM CM oo i CM co CO o Q. I- O O O O O O O O O O O O O O O O O O O O O I o

§ co

O co

U so O O O O O O O O O O O O O O O O O O O O O I o to

CO m O O O O O O O O O O O O O O O O O O O O O I o to co n« O O O O O I O O O O O O O O O O O O O O O I o to

CO to O O O O O I O O O O O O O O O O O O O O O I o

CO to

_C - Φ Φ Cn Λ fO > (fl 3 O θ, o μ ι tιi H Φ H H tq H O O D Φ --! -H -H a ci en w w - > - x s - s -

TEST B The compounds evaluated in this test were formulated in a non- phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Houieuffl vulgare). bedstraw (Galium aparine). blackgrass (Alopecurus myosuroides). chickweed (Stellaria media), corn (Zea mays), cotton (Gossvpium lι siϊ-___Q), crabgrass (Digitaria sanguinalis). downy brome (Bromus isstfflQlffi), duck salad (Heteranthera lin Qsa), giant foxtail (Setaria faberii). lambsquarters f ⁽ - ^h eηopo iyτn album), morningglory (Ipomoea hederacea). pigweed ^A"?pr ^flr>thl1H retroflexus). rape (Brassica napus). ryegrass ⁽ T olttim multiflorum), sorghum (Sfirghuffl bicolor) _τ soybean (Glycine max), speedwell (Veronica persica). sugar beet (Beta vulgaris), velvetleaf ( Abutilon theophrasti). wheat aestivum). wild buckwheat (Polvgonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli). rice (Orvza sativa). and umbrella sedge (Cyperus difformis). All plant species were grown using normal greenhouse practices.

Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty- one days after application of test compounds. Plant response ratings, summarized in Table B, are recorded on a o to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result.

t

C

CO 01 O O 0 ⁾ O O O 0 ⁾ O O O O O O O O 0) CO O O 0I O 0) O 0I 0) o rH rH rH rH rH rH rH rH rH rH rH rH rH rH rH rH H

C

CO 0) O 0) O O O) O O 0) [— O O O O O O O (— O O 0) 0I O) O) O) O) O H rH rH rH rH rH rH rH rH rH rH rH rH rH c ro 0 ⁾ O O 0 ⁾ 0 ⁾ O) 0) 0) m 0) 0) O 0) 0) 0) 0) 0) co 0i co 0) O 0) so 0) co i-

H

CM σi σi o σi σi so co σi t— 0 0) 0) O) so 0i io 0) O 0) 0) 0i 0i 0i t— r— co I— H H

O 0) I 0) 0 0 0 0 0) 0) 0 0 0 0 0 0 0 0 0) 0 0 0) 0) 0) 0 0) 0) I- H H H H rH rH rH rH rH rH rH rH rH rH H

0) O 0) o o o co 0) 0) O) o o o o 0) o o m o o o) 0) O) O co 0)

SO H H H H H H H H H H H H H

0 ⁾ 0 0 ⁾ 0 0 00 00 0) 01 0 ⁾ 0 0 0 0 0 ⁾ 0 0 ⁾ 0 ⁾ 0 0 ⁾ 0 ⁾ 0 ⁾ 0 ⁾ 0 ⁾ 0 ⁾ 0 rH rH rH rH rH rH r rH H H m O SO OO Ol in OI O O J' CM O O OO OD O in O) I 0 0) 0 0) 0 1 10 0)

CM rH rH H H

CM o o o o o o i— øi oi r- o o o o o o o o o σi øi o σi σi øi σi CM H H H H H H H H H H H H H H H

0 0 0 0 0 0 0) 01 0) 0 0 0 0 0 0 0 0 0 0 0 0) 00 0) 0) 0) 0)

CM H H H H H H H H H H H H H H H H H H

O 0) O O O O O r- 0) O) O O O O O SO O O OO O O Ol O SO 0) OO O) CM H H H H H rH rt rH rH rH rH rH H rH H

0 0 0 0 0 0 00 0 0) 0 0 0 0 0 0 0 0 0 0 0 0) 0 01 0) 00 0) H H H H H H H rH rH rH rH rH rH rH rH rH rH rH H co m i σi co in co o o in o co σi i- o so o H øi in u' o σi fo eo r- co r o σi o tn o o o so co m o co o so σi σi o σi σi o σi m so co σ)

O H r rH rH rH H U H so SO O 0) O OO 0) CM OO i Ol 0) O O) O 0) 0) O O O) Ol il' O O_> eO f- 0)

H rH rH rH rH rH rH H H tn ιjι o σι σ) ø) σi ι θ ii ^, ι o o so ø) in αι σ) oo ø) σ) ^' σ) «u ø> ι- σ>

H H r 0) 0) 0) 0) 0! CM SO ^ ^, 00 0! 00 f— 0) 0) C0 C0 0) 0) CO SO OI 0) 00 CO 0)

H H H

04 oo o o o) oo ø) so ι— o so o o o o t- o ø) θ o o m ø) so co co co rH rH H H H H H H H H H σi o o o o o so øi co σi o o o o σi o o σi o o co o i- co σl oo

H H H H H H H H H r rH rH rH H o o o o o o σi o o o o o o o o o o o o o σi σi o σi oi oi

H H H H H H H H H H H H H H H H H H H H

0) 0 0 0 0 01 0) 01 0) 0) 01 0 00 0 0 0 0) 0) 0 0) 0 0) 0) 0) 0 ⁾ 0 ⁾ 00 O H H H H rH rH rH rH rH rH H

CO oo o o o o o f- ø) o so o o o o o o o i © o m o σi σi σi ø) O H H H H H H H H H H H H H rH rH H

cn φ

H Λ

_H fβ

oi o o o o 0i ro o "-* t— o o o o o o o o o c— o o o o co m so rH rH rH rH H H H H H H H H H H t- 0) O O O O 0) « O fO so o o o o o o o o o 0) 0i o oi oo oo m SO CM

SO 0) o o so o m o 0) 0i o co o m oi CM O o co so o oo 0) O) fO 0i r SO rH r rH r rH rH rH H CM o o o σi o ir o σi i— o o o o o o o σi co o σi σi o øi σi σi σi

0) 0) 0 0) 0 00 1— O in o o 0) o o) o o 0) fo o co 0i 0) 0i o> 0) in m H H H H H H H H

CM o e__n o) o o m o 0) 0) O o o o o 0) o o o 0) O 0) 0) 0i 0) O) O) m

CM

SO 0) O 0) O O O 0) 0) so o o o o o o o o fO 0) O 0) 0) O) 0) 0) 0) m H H H H H H H H H H H H a_> O 0) O 0) O ⁾ O CO CO tO CO O 0I O O> 0> O ir O) in !< O 0) CO CO OO

CM 0) o o o o r- O) o o o) o o o 0i O) O O) o o co 0) 0) O) O 0) m O CM

CO CM

0) 0 0) 0 0 i ni σi co i— o o σi σ cM øi σi o co o co σi σi o o so

σi σi ao o o o σi σ eo o o σi o o o o o i- o o σi o co eo σi oi

H H H H H H H H H H H rH rH H σi t— o oo o o iT— ^" t— so so o o o σi oo oo o m o βi c— oi t- 0) O) 0)

H H H H H H H H H CM

00 CO CO CO O O 0) SO OO CO OO O O O O) 0 ⁾ O ⁾ O C O O 0I OI 0) 0) OO 0 ⁾ H CM

I- O) ao oi 0) O o ao o) 0) 0i o o o o 0i o oi r- 0i o oi 0i O) cD 0) O)

H rH rH rH rH rH rH rH rH CM ι* oo o σi o o o m co o t- o o o o oo o o σi o t— so o e— 0) O) 0i H H rH rH rH rH rH rH rH rH rH rH H H CM

CO l- O OO O O O OO OO 0) O O O O O O O O O O O t- O I- 0) O) 0) H H rH rH rH TH rH rH r-l rH rH rH rH rH rH rH H CM

CM OI O OI OO O O Γ^ OI OI O O O C— o oo o o co oo o co øi oo oo ao ø) H H rH rH rH rH rH rH rH rH H CM

H O O O O O O f- O O O O O O O) I 0 0 0) 0 0 0) 0) 0) 0) 0) 0 H rH rH r r rH rH rH rH rH rH rH rH rH rH rH rH H CM σi o o m o u ^, o o o o m o u< o o o t- o o o o o o o o '» o o

CM

ffl φ

H ) fO

H

o σi o o r- øi co ii' σi o øi σi o oo σi σi øi σi o o σi so oi σi t- ni fo

H rH rH H rH rH to m o co

O O O O O O) O O 0) O O O O O) O O O OO O O 0) O) O O CD 0) o rH rH rH rH ri rH r-H rH rH H rH rH rH rH rH rH rH rH to

H o o o o o oo 0> 0) in o o o 0i oi 0i o 0) o o r- O) 0) O 0> t- 0) O rH rH rH rH rH rH rH rH rH rH r H CO

CM t- o o σι θ co σι nι oo o oo so ι- øi (- o cM øι øι ι- oo I oo in N to 0) CM

§ 0) o o o o o o co σi σj o o o σi in oo o oo co o t- σi σi øi r- co co OO H H H H H H H H H H H CM O

I lO Ol H OO O CO I O O fO r- OO O C OO U' O u• I O I o ι- o

O CM U m 0I O O O O OO O 0) CO O O CO O O O O CO I- 0) t- 0) O 0) 0) O) 0) t-

CM u ¹ 0) 0) 0> o o cM m 0i o so o o u ^, io 0) 0 ^{) (} o o t- ro 0i i ø> o so fo

I— CM

O O O O O O) O O tO O O O O O) O O 0) (O O) O 0) O 0) 0) 0) O)

I- CM

O o o o co o o) o o o o o o o 0) 0) o eo so 0) 0) o o o n" Oi o t-

CM

0) cn o o cM CD in o σi o fO o r- r- o ιn co r- co i ιr m o m r- <β ι— SO rH rH rH H CM

a φ

H _q

(0 h

Table B COMPOUND

Rate -(62 g/ha) 1 2 3 5 7 11 13 14 35 50 51 53 58 59 60 63 64 71 77 78 81 82 83 84 86 88 89 102 103

PREEMERGENCE

Barley Igri 8 9 6 7 2 0 3 0 3 8 9 9 7 7 4 9 9 2 6 5 9 6 6 8 9 6 8 8 9

Bedstraw 10 10 10 10 0 9 9 8 10 10 10 10 10 10 10 9 9 9 6 8 8 9 9 7 9 9 9 9 9

Blackgrass 9 10 9 9 6 8 8 6 8 9 9 10 8 8 8 10 10 7 8 8 9 10 10 9 9 9 9 10 10

Chickweed 7 10 10 10 0 10 10 10 10 10 10 10 10 10 10 9 10

Corn 4 9 10 7 0 4 9 3 6 2 10 7 8 8 7 10 10

Cotton 4 4 7 8 0 4 9 3 7 8 10 9 5 9 9 9 9

Crabgrass 7 8 9 8 3 6 4 0 8 9 10 10 7 7 6 10 9

Downy brome 9 10 9 10 5 7 7 6 10 9 9 9 7 8 7 10 9

Duck salad

Giant foxtail

Lambsquarters

Morningglory

Pigweed

Rape

Ryegrass

Sorghum

Soybean

Speedwell

Sugar beet

Velvetleaf

Wheat

Wild buckwheat

Wild oat

Barnyardgrass

Rice Japonica

Umbrella sedge

00 0) 0 0) 0) 0 00 0 0) I 0) O O) O O O O CO 0) O) O 01 O) I— I o

CM O σi oo σi σi σi co co o i v oi os oi o oi o r^ to oi oi oi oi ici ι O CM to o oo 0 ⁾ oo 0 ⁾ co 0) co I σi o m σi i— 0) 0) oo o 0i t— o o o I r- H rH rH

H

CM m oo o ø) n< so σi.ir I σi o so σi fo in io so o o so f- o u< i t-

H

O CM O øi o o σi σi so ι σi o cn σi o σi cn σ O O øi σi oo in ι I- rH rH rH H H H H t- O 0) 0) 0i o fo co 0) i co o m oo cn σi σi fo oo o t- i ⁱ σi m i

SD

SO t— iD Oi σi σi f— σi ø) i o o f— oi o) 0) O) i— o o co co i— m I O H o co o ⁾ 0) o fo co o i o o m o σi cM O CM o σi i- o oi o i

CM

CM σ o o o o o t— o I so 0i oi oi o o o o m o o) 0i o 0) i CM H H H H H H rH rH rH H H H

H 0 ⁾ 0 0 0 0 0 00 0 I 00 0 0 ⁾ 0 0 0 0 0 0 0 0 0) 0 01 I CM H H H H H H H H H H H H H H H H H

O 0) 0) 0 0 0) 00 10 0) I OO O OI 0) O O) 0) CO O O OI OI O SO I CM

H 0) i co i t— i

SO OI OI OI O OI OI OI OO I 00 0 01 0) 0 0) 0) 0) 0 0) 01 ^* 0) 00 I m cM ø øi co cn m m m i t- oo øι σι σι m σ) D> o σι oo H θ) to i

OO 0) 0) O 0) SO CO CO I O) 0) O) 0) 0) 0) O) t- O 0) 0) SO O) (— i

CM m o o σi so σi f- σi i t— σι σ) σι σ) σι o ιn o σι © a ^, σ> ιn i rH rH rH rH rH rH

H

H in o o σi in co i- σi i øi øi i- o σ eo o io σi σi σi m o o i rH rH rH H rH H

H

O 0) 0 0 01 0) 0 01 0) I O) O 0I O O) 0) O) O O OI O t— 01 0) I

H rH rH H rH H rH rH rH

H øi 0 0 0 0) 00 0) 0) 0) i σι σι co øι oι o ø) co θ) o ø) øι θ) ø) i

O H H rH rH

H oo σi o o o o o o σi i σi o o o o o o o r- o σi σi σi ø ⁾ i

O H H H H H H H H H H H H H H

ffl φ

H Λ (0

B

CO σi o o o σi σi so o I so σi σi σi ø so σi co co σi fo so σi m i l so

CM

I— σi o o o o σi t- o ι so o σi σi σi σi o co σ σi co σi σi so ι I O H H H H H H rH rH CM

SO to ø) o co ι— so in ø) i ir σi oo t— ι— co σi so σi in co to o m I I O H H CM

O) o o 0i -0) oi 0) o I σi o σi o σi o o i— σi σi t— co σi ø) ι I O rH rH H rH rH rH rH CM

01 vo 0) O 0) O co co o i 0i o m 0) 0) 0) 0) vo oo o) r- O) O) 0i ι ι m rH rH rH H

CM co oo o o o o co øi o I σi o c— 0) 0) O 0i r- _— ø) ø) co σι ø) ι ι m H H H H H H H

CM o σi o o so σi o co o i co o σi oo σi o o co σi m σi σi σi σi ι I m rH rH rH rH H rH rH

CM σi σi øi øi σi i- o σi co I I CM CM ØI O O OO CO IT O i so σi o c- σi m σi so o cD m o σi cM i i rH rH rH H

CM

CM σι o σι cM θi co t- o I so o σi o m oo σi co o σi m σi oo co l i O H rH rH rH CM

0) O 0) 0) 0) 0) t— O I t— 0l 0) 01 tO 01 O 0) 0) 0) O) 0) 0) 0) I I ro

CM o m oi oi oi co i t- t- I vo io cM co co o σi io σi in n ⁱ in σi cM I I

CO CM

§ 01 0) 0> 0i 0i so co i* r— i O O 1T 0) O CM 0) SO 0) CO 0) OO CO SO | I CM H H O CM

§ tfl i— σi m oo o σi co i I m ι θ) øι co o σι σι i co σι co σι ιr ι I

O CM H CM

CM O CO O O O O CO I o co <Jl ^ ol '» « < o ιn o oι <» i ι rH rH rH H O OO Ol OI O OO t— CO 0I ι- o m σι ιn vo σ) io σ> ø) oo r- σ> ιn ι i H H H CM t- σi σi σi o σi r- vo σi i m o co co o) a> o m o o) oo 0) co t- I i

H H H H CM r σi o co σi o o t- σi l «* o o o o r- o o eo o t- m σι ιo ι I

H H rH rH H H H H rH rH H CM O 00 0 0) 0 0 0 0) 0) I 0) 0 0 0 0 0) 0 0 0 0 0 0) 0) 1- I I H H H H H rH rH rH rH rH rH rH r rH CM

CM (0 0 0) 0 0) 10 00 00 oo αi io oi oi f oi io o oi in n oK i H H CM

H so o σi o o oo o ø) i O 0) i* o o) co o t- o o) oo p- 0) in i i

H rH rH H H H rH rH

0) o co o co o o o in i o o o o o to co o o u' o o fo o I i O

to

Φ

H

_• Q Λ

(0

EH

o oo σι σι u ^, θ) θ θ i o o t- » co cM o m o o co o ø) θ I

H rH rH m O) O) o o t- co i- 0) i σi o i- σi n' t- σi m o o so m σi so i o rH rH H rH rH to

CM σi o o o co σi σi o i σi o tΛ øi o o σi io o o σi σi o σi ι o rH rH r-i rH H rH rH rH rH H co in eo σi σi cM oo r- σi I t- o t- σi so m m co o σi vo so co m I o H H to o u' r σi i— in ir in oo I co σ) i- σ> vo ^< so (o co σι ιo so 3« ιi< o to

CM o o o o o cM O i O O O O O O H O i rr o o in o I

§ 0) CM

O 0 ⁾ m ø) øι σ) io o cM i— t I— o o o) H so oi o o oi ij ^, H co in U so o o m co o o o o i co o o o o o oo o io o m o eo o i

I- CM m o o o o o σi o o i σi o m σi σi o o so o o o o o ø) I ι- rH rH rH rH rH rH rH H rH rH rH rH rH rH

CM ir cM o cn o o o co σi i m o o m o o ^ o o o ro r- i o i i-

CM

0) O) O O l— - 00 0) 0 I 0) O) 0) OO 0) 0l lI ^, O) O U ^, OI 0) 0) I r- CM o 0) 0) 0 0 0) 0 0) 0 i 0i 0) f 0) 0) 0) O) fO 0) o m 0) 0) 0) i t- rH rH H

CM

0) O SO OI O O O H fO I O 01 O I- CM O CM O 0 ⁾ I H O 01 O I O CM

4-> φ

(0 H to (fl co ffl tn

A •H μ ι Φ co o O

-- υ a ■ ^' Φ ro Φ μ 43 (0 -H φ tn Z μ eo g tj 4-1 4 o 4-1 <M 9 μ C co ω tn to τ3 eo o to Ά H H φ (β x b) o

CM CD M 9 ea Φ eo μ H o tβ tn H Φ Φ υ 4J O a (fl ra so o- (fl - μ. Φ_ (fl .0 (fl MH 3, tn O W g C Φ Λ H S ffl μ tO H

— w >ι μ tn a c μ w σ c Φ rt 3 rt - - 3 A ^. O ^. (fl ^. . t H φ S φ +J ! Λ! 0 tn >ι 4J C0 -H Φ μ 43 φ O μ φ 4J ι φ

H Φ Ϊ- H eo o o C 4J _Q C _« C Λ C * Φ tn t_nΛ Φ (fl (fl τ) ^, a C Φ μ Λ -ι ω ^, d (0 -H μ 4 (fl * θ (0 g μ σι a φ μ ι Φ tnH Φ H H μ υ Λ

(fl (fl 2 (0 Φ H Λ O θ μ θ 3 -rl (fl θ -H (β ι θ θ a 3 Φ _! -H .H (0 τl g i _- _J m m m o u o u Q Q U ^ S ^ a ^ w c co w 3: s S ffl i- 5

Table B COMPOUND

Rate (31 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310

POSTEMERGENCE

Barley Igri 3 9 7 10 10 10 10 10 10 9 10 5 10 10 10 9 9

Bedstraw 2 10 6 10 10 10 10 10 10 10 10 8 10 10 10 10 10

Blackgrass 9 10 . 9 10 10 10 10 10 10 10 10 9 10 10 10 10 9

Chickweed 0 10 1 10 10 10 10 10 10 10 10 8 10 10 10 10 6

Corn 9 10 8 10 10 10 10 10 10 10 10 10 9 10 10 10 9

Cotton

Crabgrass

Downy brome

Duck salad

Giant foxtail

Lambsquarters 0 9 0 10 10 10 10 10 10 9 10 8 10 10 10 10 9

Morningglory 0 7 7 9 10 10 10 10 10 9 9 5 7 9 10 10 10

Pigweed 4 10 7 10 10 10 10 10 9 9 10 7 8 9 10 8 7

Rape 0 9 0 10 10 10 10 10 10 3 10 9 9 9 9 9 9

Ryegrass 0 10 2 10 8 4 10 10 7 6 10 5 10 9 10 9 7

Sorghum 9 10 8 10 10 10 10 10 10 10 10 10 9 10 10 10 9

Table B COMPOUND

Rate (31 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 PREEMERGENCE

Barley Igri 5 7 6 6 0 0 0 0 2 1 2 2 2 0 2 0 0 2 6 9 9 3 7 3 9 9 0 4 5

Bedstraw 9 10 10 10 0 5 8 8 8 8 8 9 9 10 8 9 9 10 9 10 10 10 10 10 9 9 9 2 8

Blackgrass 8 8 9 , 7 4 7 7 4 8 8 9 8 9 7 4 4 7 8 9 9 10 8 8 7 9 9 6 8 7

Chickweed 6 10 10 10 0 10 8 10 8 9 9 8 9 10 0 8 10 10 10 10 10 9 10 10 9 9 8 5 7

Corn 0 8 8 6 0 4 8 3 9 9 9 10 10 10 8 0 2 3 0 10 6 7 7 4 9 10 0 0 6

Cotton 3 3 6 7 0 4 9 3 6 7 8 5 9 9 2 0 7 9 8 10 8 4 9 9 8 9 7 0 7

Crabgrass 3 8 7 7 0 2 2 0 8 10 9 8 9 9 7 7 4 8 8 10 9 6 7 3 9 9 3 3 6

Downy brome 8 9 6 10 4 3 6 3 4 3 4 7 7 9 1 0 8 8 8 9 9 6 7 7 10 8 2 6 4

Duck salad _ _ _ _ _ _ _ _ _ _ _ -. _ _ - _ - - - - - - - - - - _ _ _

Giant foxtail 3 8 8 4 3 5 3 2 7 9 9 7 9 9 8 6 7 9 8 8 9 6 3 0 9 9 0 5 7

Lambsquarters 9 10 10 10 5 10 9 10 3 9 10 5 9 8 5 6 10 10 10 10 10 9 10 10 10 10 8 6 7

Morningglory 0 3 5 8 0 2 6 0 6 7 2 7 9 9 5 2 3 8 9 10 5 0 10 10 9 10 8 2 9

Pigweed 7 10 7 10 6 7 9 8 9 9 8 8 9 10 7 8 8 9 10 10 10 9 9 9 9 10 9 9 9

Rape 6 10 9 10 0 4 9 8 6 4 8 9 8 8 3 0 6 8 9 9 9 10 10 10 10 10

Ryegrass 6 4 2 8 0 5 7 3 5 8 5 9 4 8 3 0 6 7 9 9 10 7 10 8 10 9

Sorghum 7 8 9 9 4 8 9 5 10 10 9 9 10 10 7 5 9 9 8 10 9 10 10 8 9 10

Soybean 4 5 4 7 0 2 3 2 3 5 4 4 9 8 2 2 2 6 7 10 7 4 8 8 9 9

Speedwell 7 10 5 10 0 4 8 7 8 8 2 8 9 3 0 6 10 8 9 10 10 10 10 9 9 8 5 0 2

Sugar beet 8 10 10 10 0 9 8 8 9 9 8 8 9 10 2 9 10 10 9 9 9 10 10 10 10 10 9 9 9

Velvetleaf 6 7 5 8 0 4 8 0 7 7 8 7 9 8 3 0 5 8 8 9 8 8 10 8 9 9 9 4 7

Wheat 6 8 7 8 0 0 0 2 4 4 0 2 3 1 2 0 3 0 5 9 9 0 5 3 9 9 2 3 4

Wild buckwheat 9 10 10 10 0 6 8 7 7 7 7 8 9 8 0 0 9 10 - 9 9 8 9 8 9 8 5 6 7

Wild oat 3 5 3 3 0 0 0 0 5 4 0 3 4 3 2 3 4 3 5 9 8 3 6 6 6 5 0 0 1

Barnyardgrass _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ - - _ -- _ -- _ _ _ _ _ -.

Rice Japonica _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

Umbrella sedge _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __ _

0 σi o o o σi o c- o i m σi σi σi o o o o m o σi σi o ø) ! I 4 rH rH rH rH rH rH rH rH rH rH H

H σ o o o o o m o 1 in o σi σi o o o o o o σi σi σi σi 1 1

H H H H H H H rH rH rH rH rH rH H

O so i— o o co co so t- 1 c- o σi σi o m σi i— o o oi vo o _* * 1 1 04 r rH rH rH rH rH rH H

0 ⁾ 0 ⁾ O ⁾ O O 0) O ⁾ t- O I OO O O) 0) O O 0) CO O O 0) 0) O CO I I

00 o øi r- oo ir m cj co i H Oi vo c- vo vo co o o co csi o σi o i 1 ir σi co σi m øi vo m 1 ιn σι o σ> σ) t- σ) oo co σ) ø) o σ> ιn 1 1

H

IO CO 0) 0) 0l l_D 0) CO r- | OO O) 0) O) 0) 0) 0) OO O Ol 0) H Ol OO I 1 m o σi σi oo so csi co co I m co i— σι σι m σ ι co ι— ι— o σi o 1 ir vo σι σι oι σι n< t- t- 1 σi σ oo σi oi co σi vo σi σi i— to ø) m 1 1

H

CN u' o σi σi in co u' vo 1 m oi 9i Di βi (it o ifl o ιιι ιιι <f 1 o 1 1 H H rH rH H

H co σi o σ co vo ir vo 1 t- σi i— o σi i— ir vo co en r- in o o 1 1 H H rH rH

O 0) 0 0 0) 00 0 0) 0) I 0) 0 00 0 0) 0) 0) 0) 0 0) 0) 1— t— CO I I H rH rH rH rH rH H H

§ 0) 0) 0 0 0) 1— 0) 00 0) I 00 0) 1- 0) 0) 0 0) 00 0) 0) 0) 0) I O) I I O rH rH H H OQj 00 0) 0 0 0) 0 0 0) 00 1 eo o o o o o o øi t- o σ vo σi øi 1 1 a o rH rH rH rH rH rH rH rH rH rH H

O H u r- 0) 0 0 0 0 0 0) 0) I 0) 0 0 0 0 0 0) 0 0 0 0 0) 0) 01 I I o H H H H H H H H H H rH rH rH rH

CO oo 0) 0) 0) O 0) co co 1 1— o 0i oi oi i 0) Vo co 0i co t- 0) in 1 1 o H

H

04 1— o o oi r- ^r o m 1 ^ o ffl ιJι βι H Oι o βι (n » oι <J 1 1 o H

H

0) lo σi σi øi t- t— m m 1 ι^ o oι βι βι αι βι α oi ()i α <r ιo cι 1 1 00 H

CO vo o) 0) 0 so o) so 1 in co in co øi vø oi t- øi oi io φ σi o 1 1 CO so v 0i 0) 0i »* 0i _— so 1 oo o co eo oi in o vo øi βi co co σi i 1 1

00 H fo o co t- o oo io i ι vo oι c- t- to ιr σι oo σι ^' t- j' vo ι 1 00 H

CO r oi o o i 1 I m 1 1 σi 1 i ^β i m i ι o ø) i co oo csι ι 1 00 rH rH H

04 so ø) σi o 1 1 1 1- 1 i σi i 1 ø) in 1 1 o σι 1 in 01 1 1

CO H H oo c— σι t- ι 1 i co i ι ø) i i σi vo t 1 ø) o) 1 r- ø ⁾ t— 1 1

n Φ

H

A _q to H 5

σi oo σi i— u cN Co i— I I— σi cN tD o cN oo ir co in .— I— U« CN I I m m ø ⁾ m ι— t- σi cN m i i σi i— m o 0) c- o) i 0) i oi cN i i

0) o σ so σi o i— o i— I o co cN so vo m cN cN o øi csi o oo cN t I H ⁽ N

00 vo oo σi o m t- m ø) I T O T OO T SO SO VO I σi m io co co i i

H CN

I- lo co σi σi n ⁱ in in σ) i IT ι co i- co vo σi co σi σi c- m so m i i H CM

H< so o co σi o o so oo I co o σi σi o c- co cπ co o i- u' øi m I I H rH rH rH rH rH H CN O I— 0 0) 0 0 0 00 0) I 00 0 0 0 0 0) 0 0 0 0 0 0) 0) 10 I I H H H H H rH rH rH rH rH rH rH rH rH CN

CN o co ø) o m m t- so i ι- i in so so o vo r o so fo o in o i i H H H ? øι co ø ⁾ co vø ø) co I 0) 0) fO o oi m o vo 0) O) t- r- 0i to I I

O O O O O O O CO I O O O O O O CN O O iT O O CO O I I CN

00 0) 0) 0) 0) 0) I O O) I 0) 0) 0) O O 0> O t- 0) O1 0) 0) OI I- I I O 04

I- 1— 0) 0) 0) 0 00 0) 0) I O) 0) CO O) O) 0) O CO CO O) O) 0) OO I— I I O σi o σi oi o σi σi o I 0i o co o o) O) o i- 0i 0) 0) O) 0) co I I

H H H rH rH H

S m 01 0 0 ⁾ 0) 0 0 ⁾ 0 0 ⁾ I 0 ⁾ 0 0 ⁾ 0 0) 0 ⁾ 0 1— 00 0 0) 0) 0 ⁾ 1- I δ o H H H H H H H

O CN ir 00 0 0) 0) 00 00 0 0) I O OI t- O O OO O I- CO O OO CO CD VO I I H H H rH rH rH rH to oo i— co σi iji c— oo ø) I co σi vo σi o eo σi vo i- σi σi σi σi vo I ι o to o so σi i m so oo m i σi σi t øi cN so io σi σi ir o σi o i i

I-

CN U' CJ vo co n' r- u' I t- o m o) to m m co 0) 0) vo u« 0i o I I o o oi i- oi o o) 0) vo i 0) o a> 0) o oi 0i co o o oi 0) oo cN i I

I-

H

I— o oi 0) 0) O) O oo m I ι* o ιn oo t- ιn σ> c I ØI SO O C- IN i so so vo σi oo σi σi c- σi oo i σι oo ιn o> σ> σι ø) in o o r- t- i n< i so m o m m oo o o c o i o σi to co ω o o o oi σi m o σi o i i

CN

A Φ rt H CO rt w to tn

A IH • μ ι Φ co o O ^■ H Φ _ rt Φ μ A (fl -H Φ

CD Z μ co g O 4J 4J o 4J SM ϊ μ c OT ω tn co t) co o to « μ H H φ (0 _K tn o

^~ H ϊ tO Φ m μ H θ co tn_ H Φ Φ U 4-1 O Oι O co to* a « μ φ (O A Λ Η ' c^O C Φ - A H 3 (0 μ co H

^•~* W ι M oi } C M n σ c Φ (fl rt s A 0 rt H

Φ 2 β) 4 ! ! O tϋ !x 4-l co -H Φ μ Λ Φ Ό μ Φ 4J l Φ

H Φ ω H w o υ C 4-i A C i β A i tιι A Φ (0 ϊ> (0 ^, θ O C Φ μ

A 4-i w μ O (0 -H μ J (fl a o (0 g &ι ft φ >ι Φ tJiH Φ H H μ θ A

- - Ά (0 Φ H _C O θ μ θ 3 H (3 θ -H m |> ₁ O O ft 3 Φ A -H -H _0 -H ε

H a c iii i. ffl u u uu a Q U J a (r; n i» toa s j K D

CN CN OO O O CN C— O O I 0 ⁾ t— O O OO CO SO O O O) VO CO I CN I I

I— rH rH rH rH H CN

H σi co o o ^ co σi o I ØI CO IO CΛ CO VO ØI CN Γ- I— - ro σi øi c— I i I— CN o so co o o øi co co co i in co cN 0) in u< in cN co o cN r— øi t— I t

I— H H 04

0) O CN ØI O' O O O I l o σi o m o o cN o σi i o o oo o i I SO CN

CO m o o σi co oo m o I co cn σi co σi ir σi co iN σ fO 'j ⁱ ø r I ι vo rH rH H

CN l- σi o o i— m co i— o I ιo σι co ø) so vo σ> ι— o σi oo co σi m I i o

<M SO H co o vo m to m t- I «a ^, σ) oo r- u' o σι ιn ι— to co o co cN I I so H

CN σi o o σi σi σi f- o I oo σι co σι θ) σ) o m oι ø) c- oo σι øι i ι

SO rH rH H H CN

0) r vo o oi o t- r- o I r- o oj o ij σi σi in vo σi i- co t- I i m rH rH H H

C*l

CO co o o o o co co co I co o f- o oo σi σi i— f- t- co m cn co I I m H H H H H

CN so O) 0) o vo 0i in t- 0i i c- oi m t- 0) O) o t- 0) O) c- øi σi oo i i m H H

CN σi in o øi c- I I ir co o oo o i I O) t- 0) O) OO I I i* 00 0 0 0 0 0) 0) 0 I 0) 0) 0) 0 0 0 0 0 0 0 00 0) 0) 00 i rH rH rH rH H rH rH rH rH rH H 04

CO 0) 0 0 0) 0 0 1- 0 I f- O 0) O O O O 0) O 0) O) 0) | 0) l I i* H rH rH rH rH H CN

CN VO O O O) 0) V0 0) O) I oi oi vo o oi 0) Oi t- oo 0) O) m o vo I i f H H H H CN r- in σi in i I

O σi o o σi σi so σi o i co o f- σi σi o σi r- o o r- σi øi oo i i n« H H rH rH

CN

CN σi o σi o in m in o ιr ø) oo øι o ι— σi r- o σi m co so i I CO H H CN

H oi o oi m T 0) f- oi i SO 0) O) CO O OO O CO SO 0I 0) 0) C- O) I I CO H H CN o o m σ) in c<j cN in ^« I u< I o m co o c- csι m ιr < to σ) θ I i

CO CN

03

π) IH

— ft h - > ω » ft PI <n M ft CO A W

CO CO H Z A ft μ- ft

A ft t -J i l o i o to o oo to o o o oo I o o o o o oo o o to M -1

I I OO vø ω o vo ω o to sø vo n- vø vø o vo oo O O O O vo UI t

-1

I O O O tO O I O tn O O O O O tO I O O O O O ib O O 0) to

00

I I vo io vo tπ so o -i vo o oo vo σi o oo I o σi øi vo o o o so ω to

M I-- - • M M M M M 00

I I to o I oo o o ω so oo vø vø tn o oo i o oo oo vo o o o i n- ι

00 i I to o o ui vo n- to to ω vo oo ui o ω I ω t -i n- o vo n- o UI to

00

I i vo vø o tβ o o vø vo o o io vø vø iø i o so so σi o o o o OI to

M M M 00

■ vo oo to o to σi to vø o vo io o oo I o w ιe _- o o o eo -1

I I M SO UI OO

I i to oo o ω

I I ιi-. ω to t_n to vo

I I O t0 O O O *» O O O O O O O O I o o o o to o o o to ω o

I 1 to _c- ^> ιt ^! » ιn vo -4 o m to uι vo to ι~ι -J I tn <ι» *> ω * ct ⁾ _o ω o ω o

I I ut -i tπ tn io o tO iCi- o σi oo iπ vø n- I CO «- -I H VO VO ØI H ω

M M t- ^ι - • M M o

I I ω io so oo o o iπ oo oo co io iπ o io I o -j oo to o o vo tπ IO UI o

I o vo o tπ o o tϋ vo t-i ω vo -i o vo I oo -i -i ω vo o oo oo in

I o io o σi o o tn o o o oo tπ o o I O O OD .to -0 00 ^1 0

ISS -0/ lόSfl/IDd 6l£tO/Z6 OΛV

0) CO 01 0) OO Ol O fO C- O I— OO øl OO IO lT CO CO CN lO CO I- IO CO O O O CN CN m σi oo vo σi o t— t— O) o oo o o) 0 o m o) o m o co so co m to oo t—

CN CN

OI vo o c— o r- vo o vo o o o r- co co t— τ ι— co o oo m oo m m oo oo H rH rH H H 04

00 t— co t- O) O) ir co r- o o o t- f- vo c- 0i o o) oo m oo m vo oo oo H CN t- 0I VO CO VO O SO VO CO O C— O O t— O) 0) O t- CO 0) OO O) t- 0) tO OO CO H H rH rH H CN vo o r— o σi o to c- σi m o o o o vo o o t- o r co o vo m oo σi

H rH rH rH rH rH rH rH rH rH rH H CN

CO m o co o o 0i ir c- oi vo o o o o eo o o o o 0) VD o vo 0) co O) H H H H rH H rH H rH rH rH rH H CN

CN rø o oo vo o i- m σi co co o o m σi fo o σi o t- co i- σi vo vo oo ø) H H H rH rH H CN

0) O) O OO O) SO O) O OO O O O CO << t- O OO CO O CO I- V O1 01 Ol H H H H H H H

CN

0) o o m o o o o o o tn o o o o o tn o o o o o o o o o o O M

00 0i o o co 0) Oi 0) O) o o o o o o o o i- m o o) oo O) vo o) 0) O) O H H H H H H H H H H H CN

I— 0 ⁾ O O O ⁾ O SO O O Ol O O t— O ⁾ 0) VO O O O 0) l- OO t- O) OO 0 ⁾ 0l o H H H H H H H H H

CN

§ SO O) 0) O O O t- O O O) O O C- O O O O O OO O CO O) 0I O) 0) O) 0) o H H H rH rH rH rH rH rH r rH rH H

O CN

! t o o o o o oo o o o o o o o o o o o fo o o σi o σi σi øi σi 5l o rH rH rH rH rH rH rH r-t rH rH rH rH rH rH rH rH rH rH H

O CN u o σi o o o m o o σi σi o o o o o o o co o o σi σi o σi σi σi o H H H H H H H H H H H H H rH rH H

CN ro oo oo oi co o i— ø) o co vo o o o o o o oo m o o r- σι oo H θ) θ)

O H H H H H H H H H H CN

CO 0 ⁾ 0 ⁾ O S0 0) 00 0) ø ⁾ f0 0 ⁾ 01 0! 0 ⁾ t— 0 ⁾ O ⁾ 0) VO 01 f— 0) 0) O ⁾ O «3* f— t- H

04 oi 0i o vo co m vo 0i o4 oo oi oi 0) O 0 ⁾ vo 0) O) co t- 0) I øi o o m t- o m o o) o o o o vo 0) o o oi o o eo o o 0i o O) O) Oi m o) 0i t- I- H H H H H H H H H rH rH H

I— σi o σi o o i— fO 0) t- t- o o) in o 0) o co ir o 0) co co 0) o in 0i O H O co o) 0) o o t— m t— co t- o oo oo o co o ø) co o ø) co ι— eo cN so o O rH rH rH rH rH rH H o o ^- ir co oo o o H O oo o oo cn o co co o cΛ oo o I o o o σi N

cn

Φ

H

A rt

0I O CO SO 0) V CN CO O CO CO O VO O) 1I< CO 0) 0I O 0) 1T OO O) O O O H rH rH m σi o o σi σi m co co m o σi co co σi σi o co o σi t- σi t— oo øi i— m o O tN o o o o o cD O CD r- o o σi σi σi o o o m o co σi σi o σi ^' co o rH H rH rH rH rH rH rH r rH rH rH H

CO

0) 0 0 01 0) 1— co 0) O 0) O co 0) 0) O) O) oi o o m 0) oo o vo m m

O rH rH H rH rH rH to

O 0i O) o o o) m a_) 0) u< 0) O vo t— σi σi oo co σi σi in σi σi σi ϊ VD o O CO

CN co t- 0) oo o m ro o vo H t- 0) '3 ^, 0) o o o) u ^, C O) ^' o c O O) CN

H 0) O O O O |— O) 0) SO O 0) CO 0) O) 0) O OO O OI SO 0) 0) O) CN CO t- 0) H H H H H H CN

01 σi o o o o co t- σi o σi oo co f- o m o oo τ σi j' 0) I co o o co CO H H H H H O CN

§ 00 o o o o o i— t- øι σι o o o σ_> o vo o o o o o σι o σι σι oo σι

C5 oo rH rH rH rH H rH rH rH H H H H H H H

O 04 c- o o o o o o σi o oo o o o o o σi o o o o m σi o øi σi σi eo

00 H H H H H H H H H H H H H H H H CN

VO o o o o o o o o vo o I 0 0 0 0 0 0 0 0 0 0 0 0) 01 01 00 CO H H H H H H H H H H H H H H H H H H H H m o o o o o o oo o cN o o o o o co o ø) θ ø) o σ> o øι o fo σι

00 H H H H H H H H H H H H H H H CM u< O O 0) O O OO O VO O O O O O C- O 0) t- CO O OI O 0) C f O)

00 rH rH rH rH rH H H H H H H H H H CN

CO o o o o o o σi o oo o o eo o o o o σi r- co co σi o o co co σi CO H H H H H H H H H H H H H rH rH CN

SO ι- σ) o oo o o v o o^ o o m o o eo o o ι H ^ ^, i VO O H O t- CN m co o o co o in o σi in o øi r- σi σi o o io co σi in øi i σi r- co vo t- rH rH rH r rH rH rH

CN

IT CO O 0I O CO O CN SO O CN O O CN O O CO O O O O VO SO __< O O O t- 04

Φ t _nH Φ H H μ υ - ft 3 Φ A -H τ< rt -r) en e > rZ rZ rZ m i-,

Table B COMPOUND

Rate (16 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78

PREEMERGENCE

Barley Igri 4 6 4 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 9 9 1 6 2 8 8 0 1 3

Bedstraw 7 9 10 10 0 5 8 7 8 8 8 8 9 10 2 6 9 10 9 10 10 8 10 9 9 9 9 0 8

Blackgrass 7 7 6 5 0 6 6 0 8 8 9 7 7 4 3 3 7 7 8 8 9 7 8 6 9 9 5 6 7

Chickweed 6 10 9 9 0 10 8 10 5 9 9 7 9 9 0 7 10 10 9 10 10 9 10 10 9 8 7 2 7

Corn 0 6 7 3 0 4 6 2 8 9 5 9 10 10 8 0 2 2 0 9 3 4 6 3 9 9 0 0 4

Cotton 0 3 5 7 0 3 6 2 5 7 7 5 9 8 0 0 7 8 7 10 8 3 9 9 8 9 6 0 6

Crabgrass 0 6 6 6 0 0 0 0 7 9 8 7 9 9 2 4 4 8 7 10 9 5 4 0 9 9 0 0 5

Downy brome 6 7 5 10 4 0 5 0 2 2 3 5 5 5 0 0 7 7 5 9 9 5 7 6 9 8 0 5 2

Duck salad

Giant foxtail

Lambsquarters

Morningglory

Pigweed

Rape

Ryegrass

Sorghum

Soybean

Speedwell

Sugar beet

Velvetleaf

Wheat

Wild buckwheat

Wild oat

Barnyardgrass

Rice Japonica

Umbrella sedge

00

I I tn vo tπ l vo io l I 4-. VO I i so l l ø l I I one oi oi M

CO

I I A Iβ <k I IO ID I I 4-. V0 I I SO I l -] | I i so vo vo tπ t

M 00 I I IO 00 UI I SO VO I I UI VO I I SO I I UI I I I O SO V0 4-.

00 t I u o u b u o N o b ω u ui I to I ω to oo vo to co o to _c-

M 00

I I to oo tϋ -i vo vo tπ io tπ vo oo oo o — l I ιπ 4» vø ιυ c_o ιo to <e> 0)

00 I I o vo to it- so vø -i vø ui vo αo ui σi ui I *- o l to vo vo vo in CO

00 1 I o oo tϋ tn io vo øi oo σi so oo σi vo ui I tπ ui ^ -j so so vo ø) o

O

I I to co to ιn vø to o co o ιø co -j ιø κ- I ω o to to ui oo oo iπ to

O

I I ω io ui oo vo αo to vo o vo vo -j vo tπ I øi o oo o vo so sø ø) to i-'

I I -I V0 03 0 t I -i sø o vø

I I -J I αo vo

M I-- l-> M M M

I I OO - -] -! S0 0) t _O I0 S _O O -l O _l 0 I V ₀ 0 _I V0 OO VO O O 0) o

M M

I I O I U> -l tO C» _-> >C- 4-. -] SO 0) VO «- I *> O Ul » CO lO VO tO M

M

M M

I i o vo to ω vø vø ω in -j vø vø oo vø ω ι øi ω oo ω vo vo o o to

M M

1 I .Ck VO O -J lO VO lO VO CO VO lO CD VO OO i tn - I tO IO OO VO VO U! -C-

I I O IO O —l -J OO O —1 u> α> SO —I 00 » l tO tO A CS IO VO O

I I -j vo o so vø o oo to co sø so so vø co 0I O3 VO OO VO SO VO — I

I I A vo o αo io -J σi so tπ so oo o oo to I _ t ιo _-< ιo j ιc ω

I I O VO O O Λ IO O O --. .— σi tπ vo o i tό o io ω — I W -J O oo

M M M M I-- 1-- I-* \-> - M

I I σi o σo oo o o co io oo o vo oo o oo I o ø — i vo o o io so so

M M M M M M to

I I t-i o σi -i o vo in .— IΠ O CD OO O Ø) I tπ ui σi -i o o I σi o

M to

I I o io so oo o o o vo vo o vo vo o to I oo to o o o o vo so

I l αo o oo oo o _. ^j vo vo o ιo vo so to l cx) tπ vo vo o vo o oo to

8ZS

ZZ8S0/I6Sα/JDd 6l£W)/Z6 OΛV

co o o o in co ø) i ø) i— o o c- m cN o o o) to vo i o i. co co o oo co cN t- o i i— co vo σi o co co o ir m co co σi vo I I so in σi o r oo t— co I in r- o oi o ir cN o eo cn cN io eo c—

0) O O CO O O O O O I O CN O O O O O O O) I O O CO O I I

00 ir σi σi co co co iT σi i i co r- i— in o co vo o oo co o oo o i I so σo σi σi vo in i— m o I m σi i— i— so vo øi m o co m co oo m I I

O t- 01 «3< O O CN T I O σi CN CN CO O m CN SO H VO O t- O I l so

01 O) O) 0) 0) ^> m O) I VD 0> CO CO OI SO 0l i 0) OO CO l- 0> SO I I co m t- r- cN I I ι i so co σi o o rø co vo ø) i so co co in cn m co σi vo co σi oo I I m H N T 0) CO 0) T O) O eO I O t- 0) CO O) VO CO OO OO O) lN O 01 C I I

O SO 0) 0) SO O O SD I O t— O m vo o CO CN O T O O CO O I I oi o o co cn vo oo o) i ι— o oo σι ø) o σι m o øι t- σι oo oo I I m o o o o σi σi σi ι O OI CO O OI CO O OO O OI OO IT OI CO I I t- O O 0) O O t- O I t- 0) O) O O O O 0) O 0) O) 0) O) O) I I

IT rH rH rH rH H rH rH H rH H r o o øι σι ιn ø) σι I σi øi vo o r- σi øi t- ^' σi vo ro co co i i

IT rH rH H i— σι o o σι co ø) θ i σ) θ in σ) øι σ) βι vo o σι r- ιn σι ^< ι i T i- σi o σi oi co oo σi i vo o vo oo σi t- øi m σi øi vo eo øi i I I IT

^■ q ⁱ t- t- o m u' ^r o i co cN f- ω o cN øi t- o fO i m i M I I co co co o o co ir cn ι co τ oo eo o co σι eo o «* co σι o co i i o o so m o o cN O i H iT o m o o cN o m ^' o co ^' O i I co

m

Φ

H A υ A rt -<-| e B ι- 5

o r o iT CN oo o o i O O CN CO O O O CN O) i vo o σ> © i ro i- σi vo to m co co i m oo vo oo o o co o o øi m o oo o o ro

CN o i- øi o cN oo r- r- I σ> θ (θ ø) ir ^' in τ o o ιo cN σι o I o co o m t- ø ⁾ o co o co I CN O ⁾ to c- 'a ^, o cN o o 0) co iT io o i o H to o O O I- CO CN CN O CO I CN CN O I- T O CN O m SO tO CN CO O I o to fN O O O CN O O O O I O O O O O O O O I O O O O O I 01 C

H tO CN I- OO CN CO m I CO CO O O) m iT iT O t- 0) CN CN CO CO I

01

CN

01 cN so øi co cv ^j o o in I CN O o co o o cN o σi t- o o t- cN ι CO O CN

I CO o o σi o co t- t- σi i vo o tn oi oi in ^ to o o t- ir oi o I

J5 co rH rH H rH rH

O CN

I- o o σi o o co t- o i ^ o tn σi o r in cN o o o to σi cN ι co rH rH rH rH rH H CN vo øl O O O VO øl CO O I 0) 01 0) 0) 0 0 ⁾ 0 ⁾ 0 ⁾ 0 0 0) 0 ⁾ 0) 0 I

CO H H H H H rH rH CN m O I Oi O CN VO O O I H O) CM OO VO O O H iN 0i m O 0) O I

00 H CN

IT σi oo o o T in vD ø) i vo o in o σi cN vo o o co r- σi σi © I 00 rH rH H H CN

CO øi o o o v m vo o i iO oi in oi i o ø) cN © σ) in σι en f- i CO H H H H rH rH ■ vo O O O O O O O O I o o o o o o cN o m o o o I O I r-

CN m σi o o o m r- oo ø) I OI VO IN O) 0) SO O CN I- O) CN 0) O IT I t- rH rH rH H H

CN T O O VO O O O O O I O O O O O O O O O O O O I O I I- CN φ rt H CO co rt tn A ω •H M , W O O

*•-. υ •H Φ ea Φ M rt -H Φ t 55 M eo g "ϋ A A 0 A "W M C O ω tn co x) tn o ea H H Φ ea tn o vo ID H Ϊ CD Φ co M H O rt tn CO H Φ Φ o A Xi ft ea ffl H Cύ rβ M Φ Λ Λ * *< 3 tU l to C Φ A H ^' eo M rt H ι M tn s C M w < C Φ A rt 9 A A o rt - > H φ Σ φ 4-1 X X θ tT ⁾ >l 4J C0 -H Φ M A φ V M φ 4-1 1 Φ H Φ ia H W θ θ C 4-i A C i C Δ C S Φ tn tn A Φ rt > rt ^, 0 ^, σ C Φ M A 4-ι ω M O rt H M A rt S U rt lf M tn ft Φ M ^i Φ tn H Φ H H M O .g

(0 (Ij OH rt Φ H A θ O M θ 3 τ4. rt θ -H rt ι θ O ft 3 Φ A -H H rt -rj i-t & a, ffl m m u o o υ o Q U ι^ s o, Λ ι_ w w t w > _2 S 2 ffl α

w ro 3! ϊ! 3! < cn cn ω ω j0 50 n3 μ. nt μ- μ- T ft c Ό o o > aϊ μ- . • Ό so

00 σ o to Λ vo o ui σi to -J o o oo -i oo tπ m o ω to ui o ui vo tπ to M

M M 00

-l Ol CD O — I UI SO SO 4-< OO I 4- l OO O OO 0) 0) tO tO I ih O ID ~J ft lo

M M M M M 00 oo -j oo o oo to vo o o vo σ o -i o o o -i -J to tπ vo øi vo vo vo tπ ω

O U) U) lπ 4-. t _ lO I OO V O VO OO -J SO 4-. O O tO OO 0) -I VO -) 4-< uι σι α_> o tπ to ø) θo ι σι ιo o so .t-. co ι _θ 4-. -ι u> θ - o to co σ) iπ 0)

00

O O O M OO _ tO VO OO CD -I U) IO tO VO CO tO O UI O -] M OO OO OO U) -- \ - M 00

*- tO tO O OO U) 0) <0 4» <X) CD O O tO O VO O -J 0 0 4^ -J tn sO O tn vo o o o o tπ w oo M vo I tπ vo ω vo -i -J vo A O -i o to o ui vo oo α) t o uι o to uι uι σι -j ιo OO VO tO -J IO OO tO tO O øl O —I O OO OO OO OO ω o

IO SO OO SO VO OO O O I o o o o o o o σi o oo tπ o o O O O -I

O

M o oo oo -i -i o ω σi o I o vo -J vo oo o o to vo ω o o o o oo o ø)

M M o oo oo oo vo oo to oo vo oi oo vo o o oo tn o cn vo so ii- oo itk io o oo o so

M M oo cs oo vø vø to to o oo o oo o o co 0 -l lO SO «- CD VO VO O SO O o

M M M M M M M M

00 —I 0) 0) 0 0 4-. O O -J O O 0 O 4-. O OO O O IO OI O SO OO

M

- co σi ui -i tπ oo oo vo oo to σi o o o o o σi tπ o oo co oo o iø ø) to

— I α> co in ] Λ oo ø) vo oo _^ j ~j ιo σι -) tπ ø) 4-. 4-. o — I VO -J IO SO ØI »

M

M M rø -j oo o ∞ ₄ -. to uι to ∞ oo ω ιø (_~ι sø ιπ uι o o o oo vø ιn _t ø o u _! ςπ

M

M M M M M

VO -1 0l i_-> IO O IO VO OO ( IO VO -l O U1 4-^ 0l tO O VO 4-. O OO O 4-> 0)

M M \-> \-- Y- ⁱ oo o) (_-i t-) vo o o) vo o vo -i tn io tn o o o m o o sD O O -i o o -i

M M

-i Λ U) θ θo o o ω 4-. o o 4i so o oo o o to o o t_o o o σ) io o oo

M M M M M M M M M >-• * M vo σi σi oo o io o σ so o io so o o o o -j αo vo o so o o o oo io so

M

M M M M M M M M M M M M M IO

OO (jJ UI iJ-. O tn O O O O O UI O O O O 0l 01 -I O O O O O SO tn o i-- t-> b-* I-* - ' I-' t-* >-* i-> t-> M t

OO OO OO VO OO I O O O O SD VO O O O O -J CP CD tu O O O VO O -J M

M M M M M M M M tO oo ^i to oo io tn σi o o o oo cD O O O -^ to -i σi ui oo o o so o tπ to

2 Z

ZZ8S0/I6Sa/JDd 6l£frO/Z6 OΛV

0) i— øi øi t— co o cN vn o vo co oo r- m o co oo I C4 i- m m vo o o o CN CN m co i— m oo o) vo io vo o so o co co 0) cn co t- f 0) vo r vo ir o m o

CN H CN σi m σi so co t— IT O I O O O T I— Γ- SO Π I— tn σi r- co t— » ιη <n n

H H CN

CO m t- vo co t- ir cN i— o m o σι vo t- r vo co o σ) m τ f- τ H i— I H H CN t- co in r— cn co so in t- o so o o in σi in co vo c co in co co co o t- CN H H H CN T ιr o r- o oo o cN so co r o o σ) θ So o o (- o c o ø) iτ r co σ) H rH rH rH rH rH rH rH rH rH CN cn T O i— o σi oo c c— i— m o o σi o oo o o o o oo m o m co oo σi

H H H H H H H H H H H CN

CN t- øl Cθ m θ SO '3' VO CO I- O O C CO CN O VO O t- CO ιT OO lT VO CO OO H H rH rH H CN

H σi co oi co co T cn σi σi oo o oo eo vD r i— σι r- co co r~ ι- m σι co σι H CN

O) O O CN O O O O O O O O O O O O CΠ O O O O O O O O O O O CN

CO r- o øι t- σι ι— co ιn σ> o o o o o r- o vo f o r- ιo r- ιn σι σ> σι O H H H H H H H H CN

I- i— co o t- o so o o oi o 0i r- m o) vo o oo o oo m t- t- co t- 0) O) O rH H rH rH H CN

§ VO 0) 0) O O O T O O O) O O i— O O) O O O CO O t- f- O) 0l O) CO 01 O H H H rH rH rH rH rH rH rH rH H O CN

Im O O O O O OO O O 0) O O O O O O O O t ) O O O> 0) 0) OO 0) O) D o rH rH rH rH rH rH rH rH rH rH rH rH rH rH rH rH rH

O N

IT σi σi o σi o i _T o σi w co o o o o o o o ^i o co co σi σi in vo σ) o H H H H H H H H H H H

CN ro ι- r- σ) i- o vo oo σ) i- m o σ) o ø) » θ f- m o t- m oo ι- H σ) t- o H H H H H

CN en σι ø) θ ιτ oo m eo øι o σι σι oo σι vo σι oo σι CN σι m øι oo oo o o τ t-

CN σi vo o m co m m co o co σi øi oo o vo vo co oi oo vo σi σi vo o o cN i- H

H

O ir σi øi o o σi o T oo o o σi o o co o co σi o σi co σi co co vo I- H H H H H H H H H øi σi co øi o t- d øi so iT o c- m σ oo o oo o o t- oo vo oo o o σv vo H H H H

VO vo σi co o o m m i— cD m o cD T σi oo σi co i- o co co so co o T σ) vo H H H H

H in o o o o o r- o o o o r- o co σi O N m o r- eo o I o o o βi

CN H

A φ

H co rt to co tn co υ •H M ι Φ co o τ3

A 53 -H Φ __ rt Φ M A rt -H Φ

^»■ - H M CO g O 4-1 A O A <H 9 M C co tno tτι co Ό t O 01 M M H H Φ (0 X Ci O i- H Φ eo M H o rt tn to H Φ Φ O 4-1 O ft rt m co w co M Φ rt A rt Ή 3 J5 ttnn Ό t ⁾ co g c Φ A H 3 rt M rt H

— a .ι. M.. t_n s_ C „ M.. m σ . G.. Φ - rt ., 3_ e.a- 9- A O CO ^ H

Φ , . φ 4J _ϋ! θ tT ⁾ ι A CO -H Φ M A Φ O M Φ A _^ I φ

H Φ IH H C0 O ϋ C A A C _i C A C i Φ Cn t3i A Φ rt > rt '0 ^, σ C Φ M A 4J W M - rt -H M 4-l rt ϊ θ rt M & ⁾ ft Φ M ι Φ U ⁾ H Φ H H M θ A rt rt O rt H A O O M O S -H rt O -H rt ^ O O ft S Φ A -rl -H rt -rl g α & _J oj ffl m u o u o Q Q ϋ ^ S ι-j i-i -; w tQ w s a s ι-j c-; 5

σi σi o o o m i- σi o o σi co co σi o o so i σi cn σi o σi o eo co r- ri rH rH rH rH rH H

CD O O O O t— t- O O 0) O OO O) 0) O ⁾ O r- O 0) 1T OI O 0) O CN lT rH rH rH rH H H H H σ o ⁾ 0) O OT O (- co I © io o oo o co in o in cN 0) ^' 0i o 0) o m co t- H H rH rH rH rH in vo øi o vo o o m o o o r in vo o vo o o o o co vo v o tN © o co VO 0 ⁾ 0 ⁾ 0 ⁾ O VO O CO O CN O O ⁾ CO 0) I— O) 0) O O) C) — ^< 0) l— O O O vo øi o o t- σi t- o σi o c I co σι oι oo © σ) t- σ) t- co σ) co © so cN o vo o) O) O 0) o o i- o vo I O CN VO O OI CO O O CN CO I- in o o o vo

CN

0) 0> 0) r- o o 'J' 0) O o eo o 0> o 0i o r- o r- cN f- o i- oo eo co so H rH rH rH H

CM

0) i- m 0) f 0) o o oi o 0) O vo O) co 0) o t- o 0i r r- © oo m i_— o m H H

CN

CO σi σi σi σi o o oo σi o o o o øi o øi o σi o σi oo i— σi σi ^ o σi m H H H H H H

IN IO OO 0) 0) OO © O t- O) O 0) 0) O) CO 0) 0 ⁾ O m O VO t- !- 0) OO O CO OO m

CN m ø) co θ) i— oo o vo cN θ θ σ) oo σ) τ α> σ) θ ø) θ o σ) Vθ o vo cn m

CN

2 CM vo o σi co øi oo cN øi o so ι co ιn σι o σ> co cN in ιr ιn i <f o <J ID

5 m O M

∑ m σi o o o o t— co co f— co co o o o øi o σi ^i øi co co øi øi co co co O "f H H H rH rH rH rH U CM

IT i— o o o o co oo o ir o m o o o σi o σi o o co vo eo σi o m co IT rH rH rH rH H H rH rH rH H H CN cn σi o o o o co σi o t- σi o o o o o o øi o o co o σi o αi oo r- T rH rH rH rH H rH rH rH rH rH rH rH rH rH H CN

CN o o o o o oo oo o oo σi o o o o o o σi i o oι o o o so t- co

H H H H H H rH rH rH rH rH rH H rH rH rH CN

O) O O © O CO CO 0> VO © 0> O O) O 0) O O CO 0> t- O) © 0) CN © OO T H H H H rH rH H rH rH H CN

© 0i o o o o ^ ^, vo oi m oo oi 0) © 0) O 0) eo p ^r ) 0) m 0) O 0i o fO f- T rH rH rH rH rH H CN

CN r- tD Oi o oo v ^i oo o ro o t- ir m vo o o) i i— oo oo t— o o © CO CN vo o) 0) T oo m oo © m oi oo o 0i oi 0i O) i ØI CO ØI CO OO O CN O co

C

O vo vo σ) <n co o o ιn cN in θ) σ) co vø o co co o cM vθ io t- o o o ro CM.

A tZ ^{■ '}

S KI H tn O tn o, H 9

CQ co H rt — ^■ ≤ ι M φ 0) A

H Φ H H Cθ

A A W M O rt rt O tO Φ

& c ^' c ^' , ^' _<

O t— ø ⁾ i— ιn oo ^« a ^, cM in o vo r- σι ιn σι o oo co σ ⁾ θ co m co ιn o o © H ro in σι © o ø) ø) CM i— oo cM 0 ⁾ O) t— t— σi m o oo σi øi ^r co i t— vo vo CN © rH rH H co

CM o o σi o o t- σi σi co σi o σi oo σi øi o o o o vo σi vo σi t- cn vo O H H H H H H H H CO

H 0) © o o) O) ^ ^, vo o) o oo o t- oo oi f— σi oo o σi cN co co σi fo cn cM © rH rH H H ro

© oi O ⁾ O ⁾ Oi oo ir vo o ⁾ co 0 ⁾ O co m o) oo t- oo oo 0) i oo oo oi iT o o © H cn

CN CN So o) co 0) iT i ^, CM O ^, m o r- O) co oi © m oi cM O t- iT O o o

01

CM σi σi o σi σi i- co øi cN O øi oo σi σi σi o w o co vo σi σi σi o iN ro

0)

CN

Z ø) αD σι o oι o r- ι- σι © σι oo f- l- o ιτ øι eo τ σi fM t- I vo o o vo £__> oo O CN i _ 00 σι o © o o vo <' σ) σ) ø) θ o co o m o o σ) © σ) oo o σι co oo σ)

O co H H H H rH rH r rH rH rH H

CJ CN

I- o o o) © © 0) co © <ro o 0) © o © oo © o © O H m o 0) c- t- o 00 rH rH rH rH H H H H H rH rH H H CN vo O © O O © 0) O ⁾ O CO O O O O O O O © O © O) O O OI VO CO O

CO H H H H H H H H H H H H H H H H rH rH CN m 0) O O) O O O V O © O O O OO O O O 0) O OI O 01 O m O CN VO

00 H rH rH rH H rH rH rH H H H H CN

IT o o σi o o co in σi in σi o o co o ir o σi vo I o σi I øi o tn co 00 rH rH rH rH rH rH rH rH H CN en 0i o o o o © cD O co o o) vo o o o) O O) m co t- 0) © o vo r- O) oo rH rH rH rH rH rH rH rH rH rH rH rH

CN so vo cN co o co o o m o o o m m o o co o o o o T o ^ ⁱ o o o I—

CN m CO SO O VO O 1T CO O) CN O 0) VO OO O ⁾ 0) O m O 0) H 0) O O) O OO T t- rH rH H H H

04 o o oo o o o o T o o o o o o o o o o o o m i co o o ©

I- CN

4-> φ

~ 1- H to rt co rt CT)

(0 •H M ι Φ co υ Ό

A 2 ■_-. Φ rt Φ M A ea -Ή Φ

^■ ^ w M CO g O A A 0 A <M S M C CO tn ϋ tn CO T) eo o rt M M H H φ rt _*< tn o cc. H S tfl φ eo M H O rt tn _, H φ φ u J O ft rt ^β Ξ- _* (O M Φ (O A rt Η d O ' C φ A H 3 rt M rt H , M tn S C M co σ c Φ rt 9 4J A 0 C0 κ> H

Φ Ξ O Qi) A 4 X X X X θ O tCnJi Plι A 4J CO0 ⁾ -τH1 ΦΦ M M A 4-. Φ φ V O M M φ φ A 4-> l Φ «

H Φ IH H t0 O O C 4-i A C _i<! C A C ? Φ tn tnA Φ rt > t0 ^, O ^, C Φ M

A 4-i W M O rt -H M 4-l t0 » O ⁽ 0 g M σι ft φ M t>ι Φ tnH Φ H H M O A to rt O rt Φ H A O O M O 3 -H rt O H (0 ι O O ft 3 Φ A H .H rt -r-l f- tx ι_ ffl m m u o u t__) Q Q C3 ^ s c-ι α o- w w co w 3: 3: S ffl ι-, 5

Table B COMPOUND

Rate (8 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53

PREEMERGENCE

Barley Igri 2 5 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 6 6

Bedstraw - 4 6 10 0 5 7 5 5 6 3 5 5 8 2 3 3 8 8 10 9

Blackgrass 5 6 6 3 0 4 3 0 7 7 7 5 5 4 2 0 5 6 7 8 9

Chickweed 4 8 9 7 0 8 8 10 2 8 4 5 9 8 0 4 8 10 9 10 10

Corn 0 4 3 0 0 4 0 0 4 4 4 4 6 8 2 0 0 2 0 7 0

Cotton 0 2 2 7 0 2 5 2 4 6 7 5 8 8 0 0 4 7 6 9 7

Crabgrass 0 5 5 5 0 0 0 0 4 8 7 6 7 8 0 2 2 5 6 9 9

Downy brome 5 6 0 6 0 0 3 0 0 0 0 4 3 4 0 0 4 4 5 8 9

Duck salad

Giant foxtail

Lambsquarters

Morningglory

Pigweed

Rape

Ryegrass

Sorghum

Soybean

Speedwell

Sugar beet

Velvetleaf

Wheat

Wild buckwheat

Wild oat

Barnyardgrass

Rice Japonica

Umbrella sedge

M O OO VO øl t— Oo m m i O O ⁾ OO CD O O CO lD C O VO CO O ^ ^, l I

H

H I— OD 0 ⁾ O O 0) O CO I O O 0 ⁾ CO O CO O ⁾ CO O O CO O) I OO I I o co tN O O ⁾ m vo m i o oo oo 0 ⁾ ii< «3 ^< m 0) o vo c i CM l l

CN H H H H cn 0i r o o co t- m 0) i vo o co o) o co co co © o t- i— o m i I co o o m vo fo o o o i o co co so ir o o o σi co o o co o i I i— CN øi i— co ir co o c i o co σi co cn m σi m i- σi so o co r i I

H H so m σ) co σ) t- σ) t- m ι vo σ) σ) σ) σ) oo σ) oo o σ) ø) o σι m ι I

H H

H m o oo co t- ir o cN CN i cn vD t- σi t- o f o r- i— m o o o i I

H H

«τ CN 0i oo co co i m m i co oo t- 0) O) co oo cN 0) 0i i— o oo c l I

H H

CN © 0i co oo cM m o c i O 0i m co oi u" m H Oi 0i co cM f- © l I

H H

H o ro σi co cM m o o l o σi m co vo co ^ co t- øi m co co o i I o vo o 0) O) c- co u O) I co o ir) 0> 0) O) 0) in 0) O) tn vo I t- I I

H H H

§ 0! eo øι © σι tn vo r- co I t- σi vo σi ø) ©) !- so oi oi m vo i m I I o H H o (___! CD •Φ o σi αi σi o i- m i ID OI OI OI OI CI OI CO N O O O OI * i i

2 O oH O I- oo o σi σi o o oo oo I oo o o σι ø) o σι o o © o r- σ) vo i i o O ^• σi co vo o oo o m I CN øi r- σi r- o σi o t- σi vo o co co i i o

H

CN in r- io co o o o cN I co m r oo i- o t- o oo oi m oi co fN I I

© H

O) ι øι oι σι vr M « ιi) i in σi vo eo σi m co ^' co σi co o r- o i i CO

00 ro «τ ø) r- H m o co ι cN i o r- co ιr iΩ in σι øι cM θ co o ι i CO

VO co oo σi m c i u' o i fl' i m i— σi ^ øi m σi σ vo o oo o i i 00 u O O t- O OO CO CM CM I CM m <* CN O CO 0) VO VO O CO O O O i I

CO O o σi øi σi i i ι r ι i σi i i o n i l oi oi i o t- cM i i CO

CN o σi øi ΌI i i i m i i σi i i øi T i i σi σi i m eo o i i CO if in o n i I i m i i σi i I OI ^- I ι t- oι i c t- ι i

m

Φ

H

A rt f-

M t

I I O OO O O CD -J O O O tn Ul O VO © I O O O O -1 4k t0 O I

01

I I o u) θ _t- ιo o to α> tπ oo co 4k to σι I n- -j --> ι_π ιo -ι vo o 0)

M 01

I I O 0) O .t- -| O O 4k O 4-. 0) O CD O I H- ft O N lC OI -J O -J

-J o -i o oo vo vo σi vo ui vo vo -i vo σ i ui cΛ Oo cn -i ω oo o o

-1

I l o i o tO Λ Oo o to o o tn to vo tπ i o to to o i -i to o to

M -1

I I O U) O O tn 4k O tO O O tπ O -l tn I O U) U) U) O 00 O O o to o

I I tO 4k U) U) 0) O U) 4k tO O3 -J U) - O I -J lπ UI O fO O> Ul tO u> t o

I I .i- vø in tn vo io ui oo -i αo o σi oo -j ι lo -i o tπ io oo -i tπ 4k to O

I I _tk OO 4-v -] VO -O 0) VO OO VO VO VO O IO I -I O -] -l SO IO S0 4k to O

0 eg

I to oo oo co vo αo øi vo oo tn oo -j co ø) oo tπ -j io — i so io o 01 z to o

I I U) tn -i -j oo o 4-. o -i ut oo ~j oo o) I -J -j σι σ> ιo σo αo 4k -J to o

I I U) -l 00 00 CD 00 4k O CS V0 V0 00 -l 00 I C0 CD 4k - 00 00 I 00 CD t o

I I O UJ O O O O O O O O O O O O I o o o o o o o o so t

M

I l o ∞ έk σi oo oo ω øi o oo oo o oo øi l σι ~j to tπ vo -ι oo to to

M

I I o o o o *ι. (_π to ω © o ω 4k ø) to I to tn o in -j oi o o to t

M

4k vo tn vo o o oo o -ι o vo vo o σι I -i tπ o o o -i o to o to

M

I I ut vo o ui io ui -J oo ui o io io vo o I -l o so σi αo iπ vo to 4k to

M

I I IO tO 4k N> ^l lO O -l tO 4k 0) O O I 0) tO U) tO O --l tO 4k -1 to

M

I I o o to to ø) θ to tπ o o -l to -i 4k i tπ to to to vo tπ o o CO to

M

I i o -j o o oo o to o o ιn σι o tπ o I ω o o o oo ._ oo o VO to to

I ι o to o ^ι σι σι *k -o o o t_o to -ι o O O OO tO I 4k O O tn to to o o o to o σi o tπ o o to o σi to i o to o o o o to to so

ZZSS0/l6S /ΛDd 683 6l£fr0/Z6 OM

CM o o σi σi o cN t- oo i co o o co vo cN o o o t- π m i o i I t- CN

^■ q* co σι cN © o t- co i m vo cN t- o cM o o r m cN m vo o I I r-

CN o ^ ^• co oi o cN f- co m i cN m o t- o co o o t- oi o m m cM I I

I- CN

01 © o co o o o o © i © o o o o o o o o I O O I O I I vo

CN CO CM I- CO O CO CO O O) I © VO t- O CN O t- fO O SO O O OO O I I vo

CN r- VD Oi oi o m cN CN Oi i ^* o co f- o o oi f u' n* ro o o cN I I vo

CN vo © O CO O O O O © I O OO O O O O fO O CN H CO O I O I I vo

CN

I— t- øi r- vo co co σi i m σi cN oo m vo σi o oo r- o m σi vo I I vo

CN σi © o i— © tr m m ø) i co oo o m o vo co c o co cN ^r vo © i i m

CM

00 © vo σι øι ιn ro ^* r- i t- ø) CM eo *α ^, co ^* fM © m m cn ø) ro i m

CM vo co co o) © m cM ^* 0) I m ir © m oo 0i O) o r- oo cN t- o) oo I I

CN 0) t- oo co vo ⁱ _— OO O) CN O O) | I I O CN -O O O O ØI CN O O CO O I I t- CO 0) O) 0) C O) O) »S< CO CO f i I T cN cn o o o m t- vo I m σi vo oo o i— o m o o vo cN øi o I I IT H H H H CN

CO CN 0) O 0) O O m oO | VO O) O) 0) O) 0) O OO O O) Oo m i VO I I u< rH rH rH rH rH

CM

CN ^ σi σi σi vo m eo i ia' co c oo i so u' vo o σi in c i c i I

U< CN co co o o) O) CN 0i vo i co o m σι σ vo ι- ιr σι σι cN m σι ιι< I I

13* H H CN

O m σi σi σi vo co vo σi I <» o ιo β oι ιn oi M θi βι *<nn βι ιι ^ι I I IT CM

CN cN co m o co cN co m i cM o m ir o o oi m o cM o co m © i i O CN m vo oo o o m cN ø) I o o ^r co o o oi t- o cM t- r- o © I I

CO CN

O O O CN CO O O O O I © I O CN O O O O m CM O C O O i I CO CN

H CO ra w •H M ι

A U • - Φ rt Φ M

^• . Z M t g O A A O tn a tn eo ^* d co o rt M M H

H S CO Φ co M H O rt tn β co tr. g n II ra A ra <n a. Cn O ι M tn _ϊ C M M & C Φ βJ 4-i X X θ 3ι ι A C0 -H Φ , • r ^~ H φ 0 H to υ υ c A e e β ϊ φ & cn Φ n »> ra O '. 6 M

A A W M O rt -H M A rt S O rt l M &i ft φ tki OiH Φ H H M U A rt to 0- rt Φ H A O O M δ S Η rt ό -ri ra ^i O O ft S Φ A H -H rt 'H

H (X Oi

O CN O H* O H* O O l o I © ro o o o o r σi CN O in o I m O iT VO iT CN CN CN O I CN VO T OO O O C- O CD OI CO O OO O I o co

CN o m oo o H C iT co I in oo co co cM O CN o σi oo r o eo o i o co o cN co m o o o o I o vo o m ro © o o σι σ) θ fN H* o I o

CO

© O O m o © I O O I O O O IO H O O O CO O CM O O O I o co

O O O O O O O O I © O O O O O O O O O O O O O o o o cN i o o m o i VO CN 0I O I r- o θ) ø) θ o co co m I oo o) CM oo σ) CN m o o o o o o) o I

00 CM O H o o o vo σi oo t- I t- σ co oo øi t- σ vo o o co o t- o I 00 H H H rH rH CM m O CO m O O OO O O I O Ol CN CO CM O O O O f CN O CO O I oo

CN T t- oi o cN c c co I ιr o «τ co m o ro o o vo ro τ σι o ι CO CN

CO in σi σi σi co co co vo i co σι m oo m co t- o σι σi τ τ σι o i CO CM vo O O O O O O O O I O O O O O O O O CN O O O O O I

I-

CN m 0) CO O 01 CN t- t- 0i I iT T O lf> CN iT 0) O I— I- O 0) I I t- H

CN

O O O O O O O O I O O O O O O O O O O O O I O I I- CN

A φ

H to ra co co tn rt 1- •H M ι Φ o o Ό

A U ^{■ '} Φ ra Φ M A ffl -H φ

^- 2 M CO g -α 4-ι - ⁾ o 4-1 1-1 9 M C to tn ω tn co O co o ra M M H H Φ ra X 3 ⁾ O

IS H ea Φ co M H o ra tn CO H Φ Φ O A tJ ft rt ca oo P ra M Φ rt A 10 Η & 3 _, ttnn Ό T) tfl g C Φ A H 3 rt M tO H

— ω ι M tn ? C M w c Φ <ϋ 3 Λ 9 A 0 IO _. rH φ Σ ϋ) A X X θ tn ι A W -H M A Φ O M Φ A I φ

H φ S H i θ θ G A A β *; C A c_! 5 φ tn tn A Φ (fl ⁽ 0 ^, θ 3 β φ M

A A ω M O rt H M A rt fc CJ rt g M σι ft φ M >ι φ tn H Φ H H M υ A rt « 2 rt φ H A 0 0 M 0 3 *H <3 0 H rt ι 0 0 ft 3 Φ A *H H rt τj K Dι ffi O l- U U U U Q Q U hl £ -< K I- n (i] lιl u > ϊ ϊ !t n κ i5

so m m oo eo ø ⁾ co ^ ^< CN oo m o t— cN t- co o) co vo 0) t- m m vo o iT Oi so ,-ι

CM m o øi o o vo o m cN O CN O O O so co o o o m m σi io cN O Co

C H H H rH rH rH rH rH

H m © oo © o oo © m co ^* oi © © o o) 0) o o o 0) m oo oi so r- t-

CN

O r r- o σi o o o co o sD oo o o o ro o o o o o ir t- CM O CN co CN

0 ⁾ 0 ⁾ OO O ⁾ 0 ⁾ 0 ⁾ CO O CO VO VO O O 0) O) OO O) 0) O) 0) O) 0) O ^* O © 0) oo o eo m o o cN O O O o o r- o co cN o o I co o o m o cN ir o

H H

I— o o m o o σi o o m o o o ir σi tN i— σi o σi m o σi co o m co rH rH rH H

H vo co o co 0) ^* a> © © vo cN m 0) VO 0) t- oo co o 0) Oi O 0) CO U* vo co rH rH H

H m cM o oi iT t- oo o o o co cN σi o oi o oo oo cN m co co i— © ir vo co

H H

H m t» σι co co m o co c vo m f- co θ) i- t- ι- σ) co ι- ιτ m ^ι< t- oo vo ts m oo oi io t- vo o m o o oi o o o sD w oo t- oo r- co i- ir m oo co

H H i- o) © m o) » © t- o iT o o o o m 0) 0i ij' 0) co m _- vo vo r- r-

D o 0) 0i o co co vD CN O) 0) m o o to o o co o oo 0) co 0) I σ> oo r- co

O H H H H H H H

O O) 0I OO O m C OO CN O) CO 1T O CO OO 0) O) 0) IO VO OO t- 0) OO O) OO OO I— U O H H

H

00 ro o vo o o oi o o oo o o o oo cΛ m co o I o m o o vo m co oo o H H H rH rH rH rH rH t- r- o ø) θ θ o cN SC I O) IT O O O O O 0) O i o o ι- θ) oo vo oo σ> o H H H H H H H H H H rH rH

H CO i— co oo i— o ιc > o m o o I oo eo vo o ø) t- I ø) τ vo τ ιnι θ θ θ o

CM CO f- OO m O O O iT O CN 0) t- l- O) O CO >i3* I 0) 0 00 <* C O O O o

H

0) ro σi oo r in cM O O ^' o σi o o o o r- σi o eo co o cN O O CN CN

00 H H

CO co i- oo n' O f- o ^' o cM oo t- o oo cN i- oo oo oo fM CN m o o o o 00

IO ro io co o o cN o o o co vo vo o f- o øi m o co r tN in o t- o o CO T C O 0)'VO ^' CN O O O CN 0) SO lO 0) O 01 «3' CM CO C O "a' C CM CM O CO

CO co co oo oo m oi m o fM r- 0i 0i o vo o 0) oo I ØI CO C OO O VO VO CO 00

A φ

-~. a _* -ι tn (0 co rt ea U -H M ι Φ co υ

A Z -H rt Φ M A CO - l Φ

-^ 1-4 M 0) E "3 J A O A <H M c to tn u tn w τ) W O Λ M M H H Φ rt a tn o

C- H S rt Φ W M H O rt tn to H φ φ O A O ft ffl T W (O M Φ rt A ffl Η 3, & ⁾ T ⁾ t G Φ A H 3 tO M tO

— 2 5ι M tJ» * C M OT σ C Φ rt « S A A o to ^■ >

Φ a 0) A X X 0 Cn ι A to -ri M .. _ A, φ_ O_ M.. Φ_ _ A _ _ .ι. H Φ H H co o ϋ C A β >i C Δ fi ? Φ tn θ)Δ Φ rt rt ^, d τi C Φ

A A ω M O rt -H M A rt ϊ θ (0 g M 6l ft φ M >ι Φ tn H Φ H H M θ rt rt O rt Φ H A θ θ M 0 3 -r| (O θ -H rt >ι θ θ ft 3 Φ H τ4. rt -H h _- _- α o n u u u u Q Q U ι4 ε ιiι K i- ι7) n (f] n $ _{ S i- κ

T ø ⁾ θ ø ⁾ o o co m σι ιι< eo σ) θ i— 0) O O) co m co oo o) I t— O CN C— CO CN

CO σi σi σi øi σi m i— oi m oo oo m σi o oo o oi co co t— Ø) Ø) O CN VO CO 00 rH rH H CN m o H' O r O O OO O O O U' CN O O OO O O O O CN I O O O O

CN i— vo 0i m o o t- 0 ⁾ O 0i vo oo oo 0i 0i o ⁾ ir o m o oo o oo o t- co t- H H

CN

13* O O CN O O O O O O O O O O O O O O O O O O I O O O O f- CN

CN 0 ⁾ t- o o ⁾ o cN r- 0i o o 0) m oo co oo 0) m o o) co oo 0) O) o vo co t- r H H CN co 0) 0) 0) o co t- 0i o i— O) co eo o) i' 0i i— o θ) θ co ø) m o o co t- CN

O ø) vo eo «j< o co r- ι— o in oo i— o co «<a* o ι>' o σι o σι σι co o © r- I- CN

00 m o) O) co 0) H o so o o o oo i— oι n oι oι o α) o ** M^ o o o vo

CN I- vo 0) oi csi oo m o oo o o t- oo oo co oo 0) oo m 0) m vo vo o o o so

CM

SO u* t- o) o oi o o m o i3* o 0) o * o oi co o o o o t- "» o o o vo

CN

I— O) OO t- O O O OO O O eO OO CO Ol OO O) H< O t- O I- 0) t- VO CO H vo H H

CN

§ 0) vo m co oo o o o oo o m oo m oo t- co o i- o o o vo o r- o m o m

O CN

§ °o eo 0i oo 0) O o r- co o o o o co o) 0i o 0> o co r- r- eo eo o o co O m H H H H H υ " vo oo oo σi t- o o i- σi o t- oi øi oo oo oi o m o vo vo r- oi t- o vo vo m

CN CN vo σi σi o σi o o co o m σ t- m oo o σi co o o o m I u* o co o m

CN co o oi o oi m vo vo m t- oo o o) O) co o oo f>i oo i- m 0) i» f- oo i-

D* H rH rH •

U* m o o o o co t- σi o i- ^' O oo σi 'S' o σi o o f- ir I σi o ~ ^» co ιa

CN

CO i— σi o o o t— θ) øι ι— oo o oi o o o o σi o o oo oo σi o vo vo vo «3* CN

OJ o o o o o t— co 0> i* 0) o o o o o o o> vo o 0) 0i i o m i- i-

IT H H H H H H H H H H H H H

CN co 0) o oo o r- m oo cN O oo o r- 0) r- o oo ^p o oo vo o) O) 0) o o i—

D< CN øi eo o σi m co σi σi o o t—

A φ

— 1- H 10 rt co ffl tn rt u •H M ι Φ co o O

A 2. •<-) φ (0 Φ M A rt -H φ

^-» a M to __ g TJ A A O A SM 9 M G tn tn U & to O W O rt !<! M H H Φ rt x tn o ex. H 9 « Φ to M H o ra tn 10 H Φ Φ O A O ft rt

O <J H (0 M Φ eo A to - < ά 3 t tTnV Ό CO . g ₌ C .. Φ_ A..., H . 3 (0 M (0 H

" S >ι tJi ϊ C M CO σ C (0 3 (0 _S A A O rt tj H φ Ui 0) A X X θ tn >ι CO -H Φ M A Φ O M Φ A I φ

H Φ IH H C0 ϋ O C 4 Δ R Λ< C Δ C * Φ tn t_n A Φ rt ⁽ 0 ^, O 'd C Φ M A 4J W M O rt -H M A ra S υ rt E M σι ft φ M ι Φ tn H Φ H H M ϋ A rt f0 O rt Φ H A θ θ M θ 3 -H (0 θ -H rt t»ι θ θ ft 3 Φ _t C -H -rl « -rj l ι c ^' c a a- a υ u o a Q θ A X c c6 rύ in ιn t i > mt r-. rt. rQ κ s

Table B COMPOUND

Rate (4 g/ha) 1 3 5 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 81 82

PREEMERGENCE

Barley Igri 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 5 6 0 5 0 5 5 0 0 0 2 3

Bedstraw 2 4 7 4 4 3 2 2 0 2 5 2 0 0 3 8 7 10 8 7 9 9 6 9 8 0 4 0 8

Blackgrass 4 4 0 2 0 0 4 4 4 3 4 2 0 0 4 5 7 7 9 5 7 4 9 9 3 2 3 7 9

Chickweed 0 -o 6 8 8 7 0 2 - - 9 5 0 3 6 8 9 10 9 7 9 10 5 7 7 0 3 0 9

Corn 0 2 0 4 0 0 4 2 4 2 4 4 0 0 0 0 0 7 0 0 4 2 3 9 0 0 0 - -

Cotton 0 2 5 0 3 0 4 5 6 5 8 7 0 0 0 6 4 9 7 0 9 9 4 8 4 0 - - -

Crabgrass 0 3 4 0 0 0 2 6 4 4 5 8 0 0 0 2 5 8 7 3 0 0 5 8 0 0 4 - -

Downy brome 2 0 6 0 0 0 0 0 0 3 0 0 0 0 3 3 3 7 7 2 6 3 9 8 0 0 0 4 4

Duck salad Giant foxtail Lambsquarters Morningglory Pigweed Rape

Ryegrass Sorghum Soybean Speedwell Sugar beet Velvetleaf Wheat

Wild buckwheat Wild oat Barnyardgrass Rice Japonica Umbrella sedge

Table B COMPOUND

Rate (4 g/ha) 83 84 86 88 89 102 103 107 108 109 110 111 112 114 115 116 117 118 119 120 121 122 166

PREEMERGENCE

Barley Igri 0 0 0 3 0 3 3 4 0 6 5 0 0 0 0 4 0 0 7 3 6 0 0

Bedstraw 9 0 6 4 9 2 8 10 10 8 6 3 8 8 7 9 9 0 0 2 4 8 0

Blackgrass 9 3 8 8 8 4 8 9 9 9 9 8 7 8 7 8 5 4 9 9 3 5 6

Chickweed 9 0 4 7 7 3 6 9 9 8 9 7 8 8 7 8 8 4 9 9 9 9 8

Corn - 5 0 0 0 0 0 10 8 4 6 2 0 6 0 6 0 0 7. 4 10 7 4

Cotton - 4 3 2 0 0 3 10 9 6 4 4 3 2 0 9 8 0 7 6 9 8 3

Crabgrass - 0 1 0 1 0 0 7 6 4 3 0 0 3 0 5 0 0 5 3 0 2 6

Downy brome 3 0 0 3 4 0 4 7 2 8 5 0 0 4 0 5 0 0 8 2 5 5 0

Duck salad

Giant foxtail

Lambsquarters

Morningglory

Pigweed

Rape

Ryegrass

Sorghum

Soybean

Speedwell

Sugar beet

Velvetleaf

Wheat

Wild buckwheat

Wild oat

Barnyardgrass

Rice Japonica

Umbrella sedge

i^ φ tr M ro

to

_Ck

I I 4k VO l-> tO OO OO O t0 4k O) -l 4k V M I 4k ^k © 4k 4k lO U1 4-. o t

4k

I I O VO U1 t VO VO M 4k ^k O) 09 tO Vθ ω I U1 U1 M OO VO O 0I O to

I I O I O tO -I O 0) tO Ul U) CO tO CD fO I -J UI .I-. .tk V0 VO -J O to t lb

I I t0 <O 4k CD IO SD -J O σi S0 00 00 <__0 4k I ui ω -i o oo vo oo o to to

M M M 4k

I I O OO O 4k VO o o o tO -J -1 4k I to I 4k 4k n 00 O © 00 o ._->

I I o -ι u) θ io ιo to vo to co co ιπ vo 4k i vø ui ite σi oo vø vo ω t tn

I I o o o o -loo oω oo i o i u>ooo tn σι *. o to to in

I I tn VO 0) O O -J O CO 4> 4k O O 4k ) I -J O O tO O IO t i 01 to o tn O

I I to vo ω ui (_π o o 4k tπ uι -J θ iø 4k I σi to o tn -i vo σi o ⁰ to ⁰ 5O tn q

I I O I O O tO O O -J 4k O tO O OO O I k O | O θ i O O vo Z to

01

I i 4-. vo tπ o ø) ω o oo _ik, to -o o ! ι OI M M Λ O IO Π UI M t

01 i i o -i o to o to o to o o o o ω o i o o o o o ω o o 01 to

01

I o i O O M i to oo o o σi to σ *. i oo to o o o co ui *- -I

I i o oo o o o o o tn o o o to σ o i CΛ O O O O I O O to

-1 i l o tπ to o to o. o o o o to o i o O O tO O O øl O U) o t

-1

I l o σi o to i to o o o o ω o σi to i o ω o o o oo o to M to

-1 o ui o o o o o o o to to o o ca I ui 4 θ o — i σ o o to to -J

I i o I o o o o o o o o o o o o i o o o o o o o o 4k to -J

I I O I 4k © — l O O Jk Ul tO UI O Ul tO I VO Ut tO O O VO UT -l tn to -J

I i o o o o o o o o o o o o o © i o o o o o o o o 01 to α>

I l O VO O Λ øl l O tO t l OO IjO VO O I tO O tO tO SO SO CD O to to oo

I i o oo o to σι vo o o o to oo _tk vo M I o o to o o σi -o o

09S

ZZ8S0/l6Sfl/I_Od 6iεW)/Z6 OΛV

O CN O O O O O O I 0 0 0 0 0 0 0 © U* CN O O I © I m o o co o cN o o o I o o o m o o m o © »< cN © t- o I o cn

CM O U ^< J* m O fM O O I CN t- O t- O O O O OO VO O O t- O I o co

H © cM CN in o o o o i © ^" o o o o o o m t- o cN U* © I

© ro

© o o oo o o o o o I o o o oo o o o o o o o o o o i o o

§ H O O fO CN O O CN CN I fO in o iO fM O CN O CN C O O O © I 01 O CM

S øi o o oo t- o o o © i © o o t- o o o o σi m o o m o i

O oo U CM

00 O O t- 0I O CM "β* 00 I © O CM CO OO O O O O CO fO O OO O I 00 H rH rH CM

I- © co ιn o © <α* © o I o en o eo cn o cM O O cn o o co o I 00 CM vo o o r oi m t- so u* i r- σi i- oo σi ij' oo ^' o σi co o ^' © I

00 CM in o i U* OI O CN O O i o m o t- o o o o o ir o o t- o co

CM

H co rt ω •H M ι

A u -H φ (fl Φ M

- ^« - Z M CO E X) A A 0 tn ω tn co *0 CO O (0 ~ M H tfl H * rt Φ co M H o rt tn ___

0) « (i; rt M Φ rt A ea Ή 3 tn O

— ω ι M tn 9 C M co σ ¹ c Φ

Φ 2 Φ A X X o tn ι A co ^■ - Φ

H Φ M H co θ O C A A C __ C A β * Φ A A _-j M τ) rt -H M A (0 3: υ rt E M & ⁾ ft ι (0 ra 2 rt Φ H A O O M O 3 -H rt O H rt ι O O ft 3 Φ A H -H (0 -H

-ι Λ a, -} C U θ u u a a o A ^~ : a. m. c- _t t> uj tn ^' ι > χ s s m cmi

m co o σi o o vo o so o σi σi o oo io o σi σi o σi o m I CN O H O

CD rH rH rH H H CN

IT co σi σi o o r- fo m o vo σi m r- i— o σi oo tn oo oo co eo vo o o m 00 H H CM

CO σi co cn σi σi co m i— CN (- co «a* O) O) co oi vo © vo t- 0i co co o <N oo CO CN

CN m O 0) 0) 0) O VO t— © O t- C0 I— CO CN O) '<3* © VD O ^* 0) m © H CM

I- H CN m β a βi o oi tj ^ 'j iMo β β o iΛ 'j o io o I in u_< σι r m r- o n*

CN r u* O) 0) © o oo ii* co © vo co 0i r- oo © © co © o vo f I t- o o © m* H H rH rH

CN en vo σi o σi o m oo o m oo o oo o oo o o o w o r- m vo o co cN co u* H H H H H H H H

CN

CN oi co oi a_i o cM r- oi O 0) o a_) O o m o o) o o) vo t- 0) 0) co vo t- n* H H H H H

CN

H vo vo σi vo σi co ^r m o oo i— co r- σi cN O oo cN co vo m I co σ o co U* CN o co i— σi in o H in in o in co co σ t— t— øi in o σi in t— øi co o o o

»3< CN u* vo σι ιn ι— o r- i— oo t— co m co r- I © VO O J' CN U' CO IO O VO © o H

CN

SO r- ir o vo o cN t- σi o t- σi vo σi σi vo o t- co σi PO VD O t- o co co O H

§ CN o m o o σι u< © σι σι σi o o o σi o o o o i— oo i— oo øi m co σi O o rH rH rH H rH rH r-i rH rH rH

Oj CM

O "3* i— m o co oo o oo co o vo o t— © m vo o oo I co ι- ιj* vo ι- o co r- υ o rH rH H

CN

I- ij* O σi o o o © co t- CN o o o σi oo co © I o øi co σi vo u i- oo O H rH rH rH rH rH rH rH rH H

VO CM 00 ^* CO O CO CO "fl* I t— oo t- i— vo cM o oo o σi m cN CM ir o o I en H H

<* o © O CN t- O CO O I m o m so o o vo co o co o o o o o o cN tn

H «* m m* o vo o o © I vo m ^ m o o oo cn o fn o o o o o © co o I- I— m o o vo m m i oi o o t- oo o o o o o t- oo σi vo o o o co H H rH rH rH rH rH σi vo o vo øi © t- m σi i o o co r- t- i- o o m o t- vo σi 's' H © ©

CM H H rH rH r-t rH rH

00 m ^* I- © I- CM O SO I vo co o io t- in øi r- CN io in ^ in o t- in t- CN H t- vo oo f- 01 O T U* H* I t- o øi oo so co o o o to m co t- m cN O co CN

IO m vo øi -vo © CN N CM I t- o <_D U" CN Vo 0) io o u* ir r I — « o o m CM H H m co vo t- m r- o cθ "* I vo vD t- m oθ fl* o vo cM m ι< m vo m o o cM

CM

__ a fl Φ

Φ φ

H ?

Δ t <iJ ι Φ nH Φ H H υ rt -H ι O O ft 3 Φ A H H (0 -r| J

£H r r< en tn tn w > m-* X 9 Λ κ S

Table B COMPOUND

Rate (2 g/ha) 25 26 27 28 29 30 31 34 36 107 204 205 206 207 240 241 242 243 244 245 272 283 284 285

PREEMERGENCE

Barley Igri 0 0 0 0 0 0 0 0 0 3 2 0 - 0 2 0 0 0 0 3 0 0 0 0

Bedstraw 0 0 0 0 3 0 0 0 7 10 0 7 5 2 3 2 6 7 7 9 0 5 7 2

Blackgrass 0 0 0 2 3 0 0 0 3 9 7 8 7 0 8 5 9 7 7 8 4 6 5 2

Chickweed 0 0 - 5 7 4 0 0 6 9 8 8 5 2 0 6 9 8 9 5 3 9 9 7

Corn 2 0 4 2 4 2 0 0 0 10 2 0 3 3 3 2 3 10 5 5 0 3 0 0

Cotton 3 5 5 4 5 5 0 0 6 10 0 4 3 3 0 0 4 6 2 3 0 0 0 0

Crabgrass 0 3 3 2 4 7 0 0 0 7 4 7 3 3 0 3 0 0 0 2 3 0 0 0

Downy brome 0 0 0 0 0 0 0 0 0 5 2 4 - 3 3 0 0 0 3 5 3 0 0 0

Duck salad

Giant foxtail

Lambsquarters

Morningglory

Pigweed

Rape

Ryegrass

Sorghuitl

Soybean

Speedwell

Sugar beet

Velvetleaf

Wheat

Wild buckwheat

Wild oat

Barnyardgrass

Rice Japonica

Umbrella sedge

TEST C

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica rice (Oryza sativa) seedlings at the 2.0 and 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) _τ duck salad umbrella sedge (Cyperus difformis), and tubers selected from arrowhead (Safittaria spp.), waterchestnut (Eleocharis spp.), were planted into this soil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

Test D

Compounds evaluated in this test were formulated in a non- phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one- to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley 'Igri'), bedstraw ( f.). ιm aparine) _τ blackgrass (Alopecurus myosuroides). chickweed (Stellaria media), downy brome (Bromus tesfcΩΣHB-), field violet (Viola arvensis). green foxtail (Setaria viridis). kochia (Kochia scoparia). lambsquarters Persian speedwell (Veronica persica), rape (Brassica napus cv. 'Jet Neuf ), ryegrass ( oliiim pηι1ffflnr τn . sugar beet (jBeta vulgaris cv. "USD, sunflower (Helignthiia _pnτwιιs r.v 'Russian Giant'), spring wheat (Tritimm flt»,« γ m cv. 'ERA'), winter wheat (Trit im fl citø υm cv. 'Talent'), wild buckwheat J y on m convolvulus), wild mustard

(Sinapis arvensis). wild oat (Avena fatua), and wild radish (Raphanus Blackgrass and wild oat were treated postemergence at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table D, are based upon a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash response (-) means no test result.

Table D COMPOUND

Rate (250 g/ha) 36 PREEMERGENCE

Blackgrass (1) 10

Blackgrass (2) 10

Chickweed 10

Downy brome 10

Field violet 10

Galium (1) 10

Green foxtail 10

Kochia 10

Lambsquarters 10

Persn Speedwell 9

Rape 10

Ryegrass 10

Sugar beet 10

Sunflower 10

Wheat (Spring) 10

Wheat (Winter) 10

Wild buckwheat 10

Wild mustard 10

Wild oat (1) 10

Wild oat (2) 10

Wild radish 10

Winter Barley 10

Table D COMPOUND

Rate (125 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289 POSTEMERGENCE

Blackgrass (1) - 10 7 10 10 10 7 10 7 8 10 10 10 4 10 10

Blackgrass (2) - 10 7 10 9 10 6 10 7 9 10 10 10 4 10 10

Chickweed - 10 10 10 8 10 10 10 7 6 9 10 4 0 10 10

Downy brome - 7 7 5 3 7 5 10 7 9 10 10 10 5 10 10

Field violet - 10 9 8 2 10 10 10 6 8 8 10 8 0 9 6

Galium (1) - 10 10 10 9 10 10 10 9 9 10 10 10 4 10 9

Galium (2) - 10 10 10 8 10 10 10 9 9 10 10 10 3 10 10

Green foxtail - 9 7 9 5 10 5 8 6 9 5 10 10 3 10 10

Kochia - 10 10 10 2 10 10 10 3 6 4 6 4 6 10 10

Lambsquarters - 8 6 7 5 10 4 6 7 10 3 7 4 0 10 8

Persn Speedwell - 10 3 0 2 10 0 4 0 0 3 2 4 0 7 4

Rape - 10 10 10 10 10 10 10 10 10 10 10 10 7 10 7

Ryegrass - 10 8 7 4 10 10 10 5 2 10 10 6 3 9 9

Sugar beet - 10 10 10 9 10 10 10 6 8 9 10 5 2 10 10

Sunflower - 10 10 10 10 10 10 10 10 10 10 10 10 6 10 10

Wheat (Spring) - 6 4 7 3 8 5 - 5 7 , 6 10 10 8 2 10 10

Wheat (Winter) - 5 3 6 3 7 4 5 8 7 10 10 8 2 10 10

Wild buckwheat - 10 10 8 4 10 10 10 6 7 5 10 3 10 10 6

Wild mustard - 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10

Wild oat (1) - 10 8 4 2 10 8 10 10 10 10 10 9 3 10 10

Wild oat (2) - 9 8 3 2 10 7 10 10 10 10 10 8 2 10 10

Wild radish - 10 10 10 10 10 10 10 9 9 10 10 10 9 10 10

Winter Barley - 9 7 7 4 9 7 9 10 10 10 10 8 4 10 10

Ϊ Ϊ Ϊ Ϊ Ϊ Ϊ Ϊ 2 tn tn χo χo x. t^ ^ Q tn cn ^ σ o tii m tJ W H ^{' ■ ' ■} H- ^{' • ' • ' •} XT XT G G Xi 01 Φ o iu oi H- o tr M M tό ni βi ^~ I- ¹ - > (i φ 3 sQ φ O H Ω - I ι t rt o. o, 0, p. p. o> nι M) (u i£j Φ w 6" " H-

to ø) θ o uι uι o o αo vo — . oo o o io -i i -i co as o oo σι

M y^ y-> M M - t - t - t M M M UI oα o vo oo o o ^ _> o o so o o o o oo o o o ->.0 09 00

M M M M M M M M M 0) ui o o) 0) O (o io i o o ui © -i vo oo ui © o o ui O 0) Ui o

M M M M M M M M 00

Λ θ θ o o co o o o o -k θ -k θ <__π -ι o so o to so σ) iπ Ul

M M as o © © © o ω o © -ι m o oo ω *k © o oo oo uι o σ) to to vo

M M M M M - • i-> I- ¹ l- ¹ \-> l-^ M M M o O O O O O -k O O O O O O 00 -1 O O O Ul O 0) 0) -I M

M M M M M M o vo vo ø) ø) o vo ω ω o o (_π vo ø) so -ι ω o oo o ω o ω ω 00

M M M M ω m to to o o o o σ> o ) 0 -k -J tO J-. VO <__0 0 0) 00 --. Λ 4 to to

Λ o to to o o øi ui o o o o o o o o i to o ui o o o o to ω o to o o o o o o o o to o o o o o o o to o w o o o °to •§ ω O to o ω ui to o to to to o o o o o o to o o o ui o o o to g to D

*k uι -j ιtk υι θ ιι- u) to o o σ) vo κ> oo ω vo vo vo oo vo o -j oo ^k to

Ul to <b θ o σ) θ to to o to o to ω ._ © (_ι_) to to ω to u) ιb iπ t

0) o o o o o o o o o o o o o o o o o o o o o o o vo to

00 ω o to to o -j ω to vo vo to oo o oo -i to ui n- o to o to to 00 to

03 o o o o ω to o o to *. o o to o ω uι ω u) o to ø) to to VO

ZZ8S0/l6Sn/lDd L9Z 6l£frO/Z6 O

0) co so so o o cM c-i io t- cM o o cM in o r- i— o o oo t- m so 00 CM

00 vo fl fl t— cM m fl t- r- cs o o cn r- oo w fl in o eo vo o fl 00 H rH rH CM

01 O O O O O O O O O O O O O O O O O CM fl O O O O so

CM o fl i— t- o o io fl in oo o o o o in o o in w r- o o o o fl fl H rH rH rH rH rH rH rH

CM CM fl in o m cM cn m o o o o cΛ fl O o ro fl o oo cn oo co cn

O cn

I CM

O o cM CM o m o o o cM O iN o m o o oo o o o σi in fl fn cM U cn M ø) cM o o cM o cn fl o o o o cn o o øv o o o t- fl in o fl

CM CM cM CM o m o m m cM fl o o o cM o o o o oo o fl in o cM

H rH rH rH rH rH

CM

e O O fl O O CM O rO CM O O O O rO O O O O CM O O O ©

00 CM oo o o oo o oo cM cn o in t- oo vo o t- in o o in o o o oo o

00 H CM

0) O O O O O O O O O O O O O O O O O O O O O O O vo

CM

CM CM CM O O O O CM O CM CM O O O O O O O tn o O CM O fl vo ιn o t- vo vo (- ιo o t- © ιn fl © o © o cM ø) CM CM fl co fl H rH H

CM CM © O O m O O O O O O O O O O O O O O O CM CM O O

O ro

I CM

O o O O O O O O O O O O O O O O O O O O O O O O O U m

CM

01 O O O O O O I O O O O O O O O CM CO O O O O O CM M CM

CM CM Vo m o vo r- cM O fl co o cM oi in o o co o o o fl CM

CM 00 o o o cM o m t- o m io co io cn σi o cM CM t- O A in io i-

©

H t- ro ro o fl O 0) © in vo o) o o oo o o (n tn o) o oo oo oi t- ©

O) © O O O CM in fl O O CM CM I- O CM CO O O O O O O O © 00 rH rH en (n fl t- o oo oo oo fl co 0) CM O co 0) O o o _ ' o o o o cn

00 rH rH rH rH o fl in o cM o o o cM r- oo vo o oo o o cM CM oo o fl in σi cM ø) ι- ι- o vø o o o ι- cn o o o co o o m m o o r- r- o r- m H H H H rH rH rH rH rH rH rH H

VO fl fl ø) in vo ιn i m o t- © vo cM so fl o o m cM o o fl o m

CO

W rt tn

>! ϋ rt H . ffl

O ⁾ O O CM Cn O O O O CM O O O O O fl CM CM O I- CM CM O tn

00

CM o o o o o o © o o o o o o o m o o o m o o m o

CM © o o cM O O o o o o o m o o o o o o fl CM cn cM O cn H

CM oo o o cM o o cn tn o o o o in o σi m o o cM in o o o o o

H u i- © o cn o cn n m o cn o o cn i- oi o o o cM o o o cM ©

O rH rH vo o o o cn o o i fl o o o m cM cn cΛ o o o fl CM cn cn o n

10

I I I I I I I I I I I I I I I I I I I I 0) uι σ) M t vo σ) θ θ <o vo uι uι oo ι_π to o ι_π 4k σ) θ <__o o o -J

M O

O Q to to o o -i ω o o vo ui o to o ω o o to o ui o -j o o °° S to o i o o o o o o o o o o o o o o o o o o o o o o o o ^M S to

Ul o o o o o o o o o o o o o o o o o o o o o o o to

IO 00 o o oo o o o oooo o o o o o o o o o o oo vo

ZZ8_0/l6Sα/IOd 2LZ 6iεW)/Σ6 OΛV