| EP0142152A2 | 1985-05-22 | |||
| EP0244097A2 | 1987-11-04 | |||
| US4178449A | 1979-12-11 |
Chemische Berichte, Vol. 95, No. 12, 1962, Verlag Chemie (Weinheim, DE), R. GOMPPER et al.: "Pyrazole und Isoxazole aus Ketenmercaptalen", pages 2881-2884
CHEMICAL ABSTRACTS, Vol. 83, No. 15, 13 October 1975 (Columbus, Ohio, US), T. OKABE et al.: "Biological Activities of 1, 3, 4-Thiadiazolo (3, 2-a) Pyrimidines and S-Triazolo (1, 5-a) Pyrimidines", pages 140, 141* Abstract No. 127285r, & J. Fac. Agric., Kyushu Univ. 1975, 19(2-3), 91-102*
CHEMICAL ABSTRACTS, Vol. 87, No. 3, 18 July 1977 (Columbus, Ohio, US), K. MAEKAWA et al.: "Control of Seedling Growth by Pseudopurine and Pyrimidine Derivatives", page 153* Abstract No. 17148v, & J. Fac. Agric., Kyushu Univ. 1977, 21(2-3), 99-105*
| 1. | [received by the International Bureau on 23 January 1990 (23.01.90); original claim 1 amended; other claims unchanged (2 pages)! A compound of the formula wherein G and G1 are N or C; Rl is cl~c4 alky!' cl_c4 haloalkyl, C2C4 alkoxyalkyl, C2C4 alkenyl, C2C alkynyl, cl~c4 alkoχY' l~c4 alkylthio, halogen, CN, C2C4 alkylcarbonyl, C C4 alkylamino, C2C4 dialkylamino or C2C4 alkylthioalkyl; . |
| 2. | is halogen, N02 OR S(0)nR3l OSO2R3 C1C. |
| 3. | aloalkyl, C3C. |
| 4. | alocycloalkyl, C3C. |
| 5. | aloalkynyl or C2C haloalkenyl; is C1C4 alkyl, C1C4 haloalkyl, C2C4 ' alkenyl, C2C. |
| 6. | aloalkenyl, C3C. |
| 7. | lkynyl, C3C4 haloalkynyl, or C3C4 halocycloalkyl; is H, halogen, C1C3 alkoxy, C1C3 alkyl or R is H, halogen, j_C4 alkyl, C.C4 haloalkyl, C2C4 alkoxyalkyl, C2C4. alkenyl, C2C4 alkynyl, NC2, OR3 , S(O")nH3, OSQ2R3, phenyl, phenoxy, C2C4 al oxycarbonyl, C2C4 alkylcarbonyl, C , NHSO2CF3, C2C4 haloalkenyl, C3C4 haloalkynyl, C2C4 dialkylamino, or C ~C4 halocycloalkyl; n is 0, 1 or 2; R6 is H or F; X, Y and 2 are independently CS7 or N; and R7 is H, CN, halogen, N02, CO2R3, C2.C3 alkyl, C^C^ haloalkyl or CONH2; provided that (a) G and G are not the same, (b) R^ is not CN when X is N, (c) only one of X, Y, Z can be CR7 and (d) when x is CH3, R2 is OCH3 or SCH3, G is C, G1 is N, X is N, Y is CΞ or CCN, Z is N and both R5 and R<j are H a^d i not H. |
| 8. | 2 A compound of Claim 1 wherein G is CH and G1 is N (Formula la); or G is S and G1 is CH (Formula lb) . lb CLAIMS What is claimed is : 1 A compound of the formula wherein G and G1 are N or C; Rχ is C1C4 alkyl, Cj^ haloalkyl, C2C4 alkoxyalkyl, C2C4 alkenyl, C C4 alkynyl, C;]_C4 alkoxy, C1C4 alkylthio, halogen, CN, C2C4 alkylcarbonyl, C^^C,} alkylamino, C C4 dialkylamino or C2C4 alkylthioalkyl; R2 is halogen, N02, OR3, S(0)nR3, OS02R3, C1C haloalkyl, C3C4 halocycloalkyl, C3C4 haloalkynyl or C C4 haloalkenyl; R3 is CχC alkyl, C1C4 haloalkyl, C2C4 alkenyl, C2C4 haloalkenyl, C3C4 alkynyl, c3" 4 haloalkynyl, or C3C halocycloalkyl; R4 is H, halogen, C1C3 alkoxy, C]_C3 alkyl or CF3; 185 R5 is H, halogen, Cj^ alkyl, CχC4 haloalkyl, C2C4 alkoxyalkyl, C2C4 alkenyl, C2C4 alkynyl, N02, OR3, S(0)nR3, OS02R3, phenyl, phenoxy, C C4 alkoxycarbonyl, C2C4 alkylcarbonyl, CN, NHS02CF3, C2C4 haloalkenyl, C3C4 haloalkynyl, C C4 dialkylamino, or C3C4 halocycloalkyl; n is 0, 1 or 2; R6 is H or F; X, Y and Z are independently CR7 or N; and R7 is H, CN, halogen, N0 , C0 R3, Cj^ alkyl, l~ 3 haloalkyl or CONH2; provided that (a) G and G1 are not the same, (b) R1 is not CN when X is N and (c) only one of X, Y, 2 A compound of Claim 1 wherein G is CH and G1 is N (Formula la); or G is N and G1 is CH (Formula lb) . la lb 3 A compound of Claim 2 wherein Formula I is la; X is CR7; Y is N; and Z is N. |
| 9. | 4 A compound of Claim 2 wherein Formula I is lb; X is CR7; Y is N; and Z is N. |
| 10. | A compound of Claim 2 wherein Formula I is la; X is N; Y is CR7; and Z is N. |
| 11. | A compound of Claim 2 wherein Formula I is lb; X is N; Y is CR7; and Z is N. |
| 12. | A compound of Claim 2 wherein Formula I is la; X is N; Y is N; and Z is CR7. |
| 13. | A compound of Claim 2 wherein Formula I is lb; X is N; Y is N; and Z is CR7. |
| 14. | A compound of Claim 2 wherein Formula I is la; X is N; Y is N; and Z is N. |
| 15. | A compound of Claim 2 wherein Formula I is lb; X is N; Y is N; and Z is N. |
| 16. | A compound of Claim 9 wherein Rg is H; and RL is C1C3 alkyl, SCH3, NHCH3, CH2OCH3 or CHoSCH • . |
| 17. | Compounds of Claim 11 wherein R2 is CF3, SCF3, SCF2H, OCF3, OCH2CHF2, OCH2CF3, OCF2H, CF2CF3, CF2C1, CHF2, CH=CF2 or 2,2diflurocyclopropane; . |
| 18. | Compounds of Claim 12 wherein R3 is CH2CH2F, CH2CF3, CH(CH3)CF3, CH2CH2CF3, CH2CHF2, CF3 or CF2H; and . |
| 19. | Compounds of Claim 13 wherein R5 is H, halogen, OCH3, OCF2H, OCH2CF3, SCF3, C1C3 alkyl, OCF3, OCH2CHF2, OCH2CF3, OCH2CH2F, SCHF2', CF3, CHF2, CF2C1, CH2CF3, CH2F, CCI3, CH2C1 or CN and 5 is in the meta position. |
| 20. | Compounds of Claim 14 wherein R^ is C1C3 alkyl. |
| 21. | Compounds of Claim 10 wherein RL is C1C3 alkyl; R2 is CF3, SCF3, SCF2H, OCF3, OCH2CHF2, OCH2CF3, OCF2H, CF2CF3, CH2C1, CHF2 , CH=CF2 or 2,2diflurocyclopropane; R3 is CH2CH2F, CH2CF3, CH(CH3)CF3, CH2CH2CF3, CH2CHF2, CF3 or CF2H; R4 is H; R5 is H, halogen, OCH3, OCF2H, OCH2CF3, SCF3, C1C3 alkyl, OCF3, OCH2CHF2, OCH2CH2F, SCHF2, CF3, CHF2, CF2C1, CH2CF3, CH2F, CCI3, CH2C1 or CN and R5 is in the meta position; and Rg is H* . |
| 22. | Compounds of Claim 5 wherein RjL is C C3 alkyl; R2 is CF3, SCF3, SCF2H, OCF3, OCH2CHF2, OCH2CF3, OCF2H, CF2CF3, CH2C1, CHF2, CH=CF2 or 2.2diflurocyclopropane; R3 is CH2CH2F, CH2CF3, CH(CH3)CF3, CH2CH2CF3, CH2CHF2, CF3 or CF2H; R5 is H, halogen, OCH3, OCF2H, OCH2CF3, SCF3, C .2 alkyl, OCF3, OCH2CHF2, OCH2CH2F, SCHF2, CF3, CHF2, CF2C1, CH2CF3, CH2F, CCI3, CH2C1 or CN and R5 is in the meta position; Rg is H; and R7 is CN. |
| 23. | Compounds of Claim 6 wherein RL is C1C3 alkyl; R2 is CF3, SCF3, SCF2H, OCF3, OCH2CHF2, OCH2CF3, OCF2H, CF2CF3, CH2C1, CHF2 , CH=CF2 or 2, 2diflurocyclopropane; R3 is CH2CH2F, CH2CF3, CH(CH3)CF3, CH2CH2CF3, CH2CHF2, CF3 or CF2H; R5 is H, halogen, OCH3, OCF H, OCH2CF3, SCF3, C2C3 alkyl, OCF3, OCH2CHF2, OCH2CH2F, SCHF2, CF3, CHF2, CF2C1, CH2CF3, CH2F, CCI3, CH2C1 or CN and R is in the meta position; R is H; and R7 is CN. |
| 24. | The compound of Claim 1 which is: 5methyl2(trifluoromethyl)7[3(trifluoro¬ methyl)phenyl] [l,2,4]triazolo[l, 5a]pyrimi¬ dine;. |
| 25. | The compound of Claim 1 which is: 7(3chlorophenyl)5methyl2(trifluoro¬ methyl) [l,2,4]triazolo[l,5a]pyrimidine;. |
| 26. | The compound of Claim 1 which is: 5methyl2(trifluoromethyl)7[3(trifluoro methyl)phenyl]pyrazolo[l, 5a]ρyrimidine3 carbonitrile;. |
| 27. | The compound of Claim 1 which is: 5methyl2(2,2,2trifluoroethoxy)7[3(tri fluoromethyl)phenyl] [1,2,4] riazolo[l, 5a] pyrimidine;. |
| 28. | The compound of Claim 1 which is: 2(difluoromethoxy)5methyl7[3(trifluoro methyl) henyl] [1,2,4]triazolo[l,5a]ρyrimi dine. |
| 29. | An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of any one of Claims 1 through 23 and at least one of the following: surfactant, solid diluent or liquid diluent. |
| 30. | A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of any one of Claims 1 thorugh 23. |
| 31. | The method of Claim 25 wherein the undesired vegetation is present in wheat or barley. |
INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT
(51) International Patent Classification 5 : (11) International Publication Number: WO 90/0 C07D 471/04, 487/04 A01N 43/90 // (C07D 471/04 C07D 249/00, 221/00) (C07D 487/04, 239/00, 231/00) (C07D 487/04, 237/00, 235/00) Al (C07D 487/04, 239/00, 235/00) (C07D 487/04, 237/00, 231/00) (C07D 487/04, 249/00, 239/00) (43) International Publication Date: 8 February 1990 (08.0 (C07D 487/04. 249/00. 237/00)
(21) International Application Number: PCT/US89/03039 1007 Market Street, Wilmington, DE 19898 (US).
(22) International Filing Date: 18 July 1989 (18.07.89) (72) Inventor; and
(75) Inventor/Applicant (for US only) : SELBY, Thomas,
[US/US]; 116 Hunter Court, Wilmington, DE 1
(US).
(74) Agent: BLIGHT, Samuel, S.; E.I. du Pont de Ne and Company, Legal Department, 1007 Market S Wilmington, DE 19898 (US).
(81) Designated States: AT (European patent), AU, BB, (European patent), BF (OAPI patent), BG, BJ ( patent), BR, CF (OAPI patent), CG (OAPI patent), (European patent), CM (OAPI patent), DE (Euro
(71) Applicant (for all designated States except US): E.I. DU patent), DK, FI, FR (European patent), GA (OAP PONT DE NEMOURS AND COMPANY [US/US]; tent), GB (European patent), HU, IT (European pat JP, KR, LK, LU (European patent), MC, MG, ML ( PI patent), MR (OAPI patent), MW, NL (Europea tent), NO, RO, SD, SE (European patent), SN (O patent), SU, TD (OAPI patent), TG (OAPI patent),
Published
With international search report.
Before the expiration of the time limit for amendin claims and to be republished in the event of the recei amendments.
(54) Title: SUBSTITUTED PHENYLTRIAZOLOPYRIMIDINE HERBICIDES
(57) Abstract
Novel substituted phenyltriazolopyrimidines of formula (I), wherein G and G 1 are N or C; R is halogen, CN or an ganic group; R 2 is halogen, N0 2 or an organic group; R4 is H, halogen or an organic group; R 5 is H, halogen, N0 2 , CN, an organic group; Rg is H or F; X, Y and Z are independently CR or N; and R is H, CN, halogen, N0 2 or an orga group; exhibit herbicidal activity. They may be used inter alia for selective weed control in cereal crops.
TITLE SUBSTITUTED PHENYLTRIAZOLOPYRIMIDINE HERBICIDES
RELATED APPLICATION This application is a continuation-in-part of my copending application U.S. Serial No. 07/335,121 filed April 7, 1989, which is a continuation-in-part of U.S. Serial No. 07/221,155, filed July 19, 1988. BACKGROUND OF THE INVENTION U.S. 4,209,621, issued June 24, 1980, discloses substituted phenyl-1,2,4-triazolo[l,5-a]pyrimidines of the formula
wherein R χ is H or alkyl as anxiolytic agents.
French Patent 1,433,798, published February 21, 1966 (U.S. priority May 1, 1964), discloses 7-hydroxy- 5-methyl-l,2,4-triazolo[l, 5-a]pyrimidine as a herbicide.
EP-A-220,458, published May 6, 1987 (German priority September 28, 1985) and EP-A-217 , 218 , published April 8, 1987 (German priority- September 28, 1985), disclose herbicidal triazolo- pyrimidines of the formula
EP-A-215,382, published March 25, 1987 (German priority September 17, 1985), discloses herbicidal 7-aminoazolo[l,5-a]ρyrimidines of the formula
wherein
A is N, CH, C(alkyl) CBr or CC1.
U.S. 4,740,233, issued April 26, 1988, discloses herbicidal triazolopyrimidines of the formula
wherein
R -, includes phenyl and substituted phenyl.
J. Fac. Agric..Kyushu Univ. 1977, 21 (2-3), 99-105 discloses herbicidal triazolopyrimidines of the formula
wherein
R χ is H, SCN, SCH 3 , Ph or CH 3 ; o is H or CH- and
R 3 is SH, SCH 2 Ph or SCH 2 C0 2 H.
J. Fac. Agric. Kyushu Univ. 1975, 19(2-3), 91-102 discloses s-triazolo[1,5-a]pyrimidines with herbicidal activity. -
The present invention is patentably distinguishable over the foregoing at least in the substitution on the azole and/or the pyrimidine functionality.
SUMMARY OF THE INVENTION
This invention comprises compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or poste ergence herbicides
wherein
G and G 1 are N or C;
R χ ' is C 1 -C 4 alkyl, C-L-C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl,
C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogen, CN, C 2 -C 4 alkylcarbonyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino or C 2 -C alkylthioalkyl; R 2 is halogen, N0 2 , OR 3 , S(0) n R 3 , OS0 2 R 3 , C 1 -C 4 haloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 4 haloalkynyl or C 2 -C 4 haloalkenyl; R 3 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, or C 3 -C 4 halocycloalkyl; R 4 is H, halogen, C 1 -C 3 alkoxy, C 1 -C 3 alkyl or CF 3 ;
R 5 is H, halogen, C±-C^ alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 . alkynyl, N0 2 , 0R 3 , S(0) n R 3 , 0S0 2 R 3 , phenyl, phenoxy, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylcarbonyl, CN, NHS0 2 CF 3 , C 2 -C 4 haloalkenyl, C 3 -C 4 haloalkynyl, C 2 -C 4 dialkylamino, or C 3 -C 4 halocycloalkyl; n is O, l or 2;
R 6 is H or F;
X, Y and Z are independently CR or N; and
R 7 is H, CN, halogen, N0 2 , C0 2 R 3 , C2-C 3 alkyl, C -C-3 haloalkyl or CONH 2 ; provided that (a) G and G^- are not the same, (b) j _ is not CN when X is N and (c) only one of X, Y,
In the above definitions, the term "alkyl," used either alone or in compound words such as
"alkylthio" denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.
The term "halogen," denotes fluorine, chlorine, bromine or iodine.
The term haloalkyl or halocycloalkyl denotes mono to per-halogentaed alkyl isomers e.g. 1-fluroethyl, 1,1,2,2,2 pentafluro ethane, 2.2-diflurocyclopropane.
The total number of carbon atoms in a substitutent group is indicated by the C^-C-: prefix where i and j are numbers from 1 to . For example C 3 -C 4 alkenyl would designate propenyl through butenyl.
Preferred Compounds
Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:
1. Compound of Formula I wherein G is CH and G 1 is N (Formula la); or
G is N and G 1 is CH (Formula lb) .
la lb
2. Compounds of Preferred 1 wherein
Formula I is la;
X is CR 7 ;
Y is N; and Z is N.
3. Compounds of Preferred 1 wherein Formula I is lb; X is CR 7 ;
Y is N; and Z is N.
4. Compounds of Preferred 1 wherein Formula I is la;
X is N;
Y is CR 7 ; and Z is N.
5 . Compounds of Preferred 1 wherein
Formula I is lb ; X i s N ;
Y i s CR 7 ; and Z is N .
6. Compounds of Preferred 1 wherein Formula I is la;
X is N;
Y is N; and Z is CR 7 .
7. Compounds of Preferred 1 wherein Formula I is lb;
X is N; Y is N; and
Z is CR 7 .
8. Compounds of Preferred 1 wherein Formula I is la; X is N;
Y is N; and Z is N.
9. Compounds of Preferred 1 wherein Formula I is lb;
X is N; Y is N; and Z is N.
10. Compounds of Preferred 8 wherein Rg is H; and
R 1 is C ] _-C 3 alkyl, SCH 3 , NHCH 3 , CH 2 0CH 3 or CH SCH 3 .
11. Compounds of Preferred 10 wherein
R 2 is CF 3 , SCF3, SCF 2 H, OCF 3 , 0CH 2 CHF 2 , OCH 2 CF 3 , OCF 2 H, CF 2 CF 3 , CF 2 C1, CHF 2 , CH=CF 2 or 2,2-diflurocyclopropane;
12. Compounds of Preferred 11 wherein R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 ,
CH 2 CH 2 CF 3 , CH 2 CHF 2 , CF3 or CF 2 H; and R 4 is H.
13. Compounds of Preferred 12 wherein
R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF3, C 1 -C 3 alkyl, OCF3, OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 C1, CH 2 CF 3 V CH 2 F, CCI3, CH 2 C1 or CN and R5 is in the meta position.
14. Compounds of Preferred 13 wherein R-L is C 1 -C 3 alkyl.
15. Compounds of Preferred 9 wherein Rl is C-L-C3 alkyl;
R 2 is CF 3 , SCF 3 , SCF 2 H, OCF 3 , OCH 2 CHF 2 , OCH 2 CF 3 , OCF 2 H, CF 2 CF 3 , CH 2 C1, CHF 2 , CH=CF 2 or 2,2-diflurocyclopropane; R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 , CH 2 CH 2 CF 3 , CH 2 CHF 2 , CF 3 or CF 2 H;
R 4 is H;
R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , C2-C 3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 C1, CH 2 CF 3 , CH 2 F, CC1 3 , CH 2 C1 or CN and R 5 is in the meta position; and R 6 is H.
16. Compo.unds of Preferred 4 wherein R-t is C-L-C5 alkyl;
R 2 is CF 3 , SCF 3 , SCF 2 H, OCF 3 , OCH 2 CHF 2 , OCH 2 CF 3 , OCF 2 H, CF 2 CF 3 , CH 2 C1, CHF 2 , CH=CF 2 or 2.2-diflurocyclopropane;
R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 , CH 2 CH 2 CF 3 , CH 2 CHF 2 , CF 3 or CF 2 H;
R 4 is H;
R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , C2-C3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 C1, CH 2 CF 3 , CH 2 F, CC1 3 , CH 2 C1 or CN and R 5 is in the meta position;
R 6 is H; and
R 7 is CN.
17. Compounds of Preferred 5 wherein R 1 is C 1 -C 3 alkyl; R 2 is CF 3 , SCF 3 , SCF 2 H, OCF3, OCH 2 CHF 2 ,
OCH 2 CF 3 , OCF 2 H, CF 2 CF 3 , CH 2 C1, CHF 2 , CH=CF 2 or 2,2-diflurocyclopropane; R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 , CH 2 CH 2 CF 3 , CH 2 CHF 2 , CF3 or CF 2 H; R 4 is H;
R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , CJ-C 3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 C1, CH 2 CF 3 , CH 2 F, CCI3, CH 2 C1 or CN and R 5 is in the meta position;
Rg is H; and R 7 is CN.
Specifically Preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:
5-methyl-2-(trifluoromethyl)-7-[3-(trifluoro- methyl) henyl] [l,2,4]triazolo[l,5-a]pyrimi- dine;
7-(3-chloroρhenyl)-5-methyl-2-(trifluoro- methyl) [1,2,4] riazolo[l,5-a] yrimidine;
5-methyl-2-(trifluoromethyl)-7-[3-(trifluoro- methyl)phenyl]-pyrazolo[l,5-a]pyrimidine-3- carbonitrile;
5-methyl-2-(2,2,2-trifluoroethoxy)-7-[3-(tri- fluoro ethyl)-phenyl] [1,2,4]triazolo[l,5-a]- pyrimi ine;
2-(difluoromethoxy)-5-methyl-7-[3-(trifluoro- ethyl)phenyl] [l,2,4]triazolo[l,5-a]pyrimi- dine.
DETAILED DESCRIPTION OF THE INVENTION Synthesis
Compounds of general Formula I can be prepared using one or more of the reactions and techniques described in Schemes 1-8 of this section as well as by following the specific procedures given in Examples 1-15.
Scheme-1 illustrates the reaction of aminoheterocycles of Formula II with an appropriately substituted diketone of Formula III to afford desired compounds of Formula la where R-, is alkyl, alkenyl, alkoxyalkyl, alkyl substituted by halogen and R 2 , R . R j and Rg are defined as above. This reaction is carried out by heating the reactants neat or in an inert polar protic or aprotic solvent at temperatures between 50° and 130°C. Suitable solvents are glacial acetic acid, ethanol, ethanol, dimethylformamide, and dimethylsulfoxide. Aminoheterocycles of Formula II can be prepared by synthetic methods reviewed in "The Chemistry of Heterocyclic Compounds" Volumes £ (1953), 22. (1967), and 21 (1981), John Wiley & Sons. Beta-diketones of Formula III can be synthesized by standard Claisen acylation procedures such as those taught by C. R. Hauser e . al. in Journal of American Chemical Society 67, pg. 284 (1945), , pg. 2742 (1946), ££ pg. 2649 (1947) and 7J2 pg. 4023 (1948).
Scheme-1
II III
la la
A minor regio isomer la' can also be formed in the reaction shown in Scheme-1. Compounds of Formula la are isolated pure, however, after aqueous workup, trituration, and subsequent purification by
recrystallization or silica gel column chromato- graphy. Silica gel column chromatography can also be used to isolate products of Formula la directly from the crude reaction residue obtained after reaction work up.
Scheme-2 illustrates the preparation of compounds of Formula la (where -^ is hydrogen, alkylthio, or alkoxy and R 2 , R 4 , R5 and Rg are defined as above) by reaction of aminoheterocycles of Formula II with compounds of Formula IV where Q is a suitable leaving group such as dimethylamino, methylthio or methoxy. This reaction is carried out by heating reactants II and IV neat or in an inert polar protic or aprotic solvent such as glacial acetic acid, ethanol, methanol, dimethylformamide, or dimethylsufoxide at temperatures between 50° and 130°C. Compounds of Formula IV can readily be prepared by one skilled in the art by known methods. Scheme-2
II IV
Scheme-2 (continued)
la
Scheme-3 illustrates the diazotization of compounds of Formula V (prepared by the method shown in Scheme-1 where R 2 = NH 2 ) in an aqueous acid medium of Formula HL (where L is equal to halogen) to give compounds of Formula Ic where R 2 is halogen and G, G', X, Y, Z, R- j _, R 4 , R 5 and Rg are defined as above. Acetic acid can be used as a solvent in this diazotization reaction to enhance the solubility of V in the acid medium. The diazotization is conducted intially at temperatures between 5° and 25° and subsequently heated at 30°- to 100°C or maintained throughout at room temperature.
Scheme-3
V Ic .
Scheme-4 illustrates the reaction of compounds of Formula VI (where K is O or S, G', X, Y, w, Z, R χ , R 4 , R- and Rg are defined as above) with an alkylating agent of formula R 3 -Q' (where Q' is a suitable leaving group such as halogen and R 3 is defined as above) in a polar protic or aprotic solvent such as aqueous dioxane or dimethylformamide in the presence of a base such as a metal carbonate, metal hydroxide or metal alkoxide (where the metal is sodium or potassium) at temperatures between 0° and 70°C to give compounds of Formula Id. Compounds of Formula VI can be prepared by the method shown in Scheme-1 where R 2 equals mercapto or hydroxyl . Oxidation of compounds of Formula Id (K is S) with one equivalent of oxidizing agent such as 3-chloroperoxybenzoic acid, sodium periodate, or hydrogen peroxide in a suitable solvent such as
16
methylene chloride (in the case when 3-chloro- peroxybenzoic acid is used) at temperatures between 0° and 40°C gives the corresponding sulfoxide derivatives of Formula le (where n is equal to one) . Use of excess oxidizing agent under these same conditions gives the sulfone derivative le (where n is equal to two). Substituents G, G', X, Y, Z, R-, ,
R, '6 on Id and le are as defined above. Scheme-4
VI Id
le n is 1 or 2
Scheme-5 illustrates the preparation of compounds of Formula If (where G, G -t , X, Y, Z, R-^, 4 , 5 and Rg are defined as above) by reaction of compounds of Formula Ic (where R 2 = halogen) with metal alkoxides and metal haloalkoxides of formula R 3 0"M + (where M = Li, K, or Na and R 3 is defined as above) by heating in polar protic or aprotic solvents such as tetrahydrofuran or dimethylformamide at temperatures between 25°C and 140°C. Scheme-5
Ic I f
Scheme-6 illustrates the reaction of aminoheterocycles of Formula VII with an appropriately substituted ketone of Formula VIII (where Q* is a suitable leaving group such as halogen) to afford compounds of Formula Ig (where R 2 is alkyl or haloalkyl) . The reaction is carried out by heating reactants VII and VIII neat or in an inert polar protic or aprotic solvent such as ethanol,
methanol, dimethylformamide or dimethylsulfoxide at temperatures between 50°C and 130°C. Amino¬ heterocycles of Formula VI where X=N can be prepared by methods such as that taught by H. G. 0. Becker et al., Tetrahedron, 24, 2687 (1968). Scheme-6
VII ig
Scheme-7 illustrates the preparation of compounds of Formula Ih by cyclization of compounds of Formula IX with an acid anhydride or an acid chloride (for R 2 = haloalkyl) or an orthocarbonate (for R 2 « OR3) as taught by Y. Tamura et al., J. Het Che .. 12, 107 (1975) and W. Kantlehner, Synthesis. 73 (1977).
Compounds of Formula IX can be prepared from compounds of Formula VII by reagents such as hydroxylamine-o_-sulfonic acid, o_-mesitylenesulfonyl
hydroxylamine or fi-diphenylphosphinylhydroxylamine as taught by K. T. Potts et al., J. Orσ. Che .. 31, 260 (1961) and Y. Tamura et al., Tet. Lett.. 4133 (1972) and W. Klotzer et al., Synthesis. 592 (1982).
Compounds of Formula IX where X=CR 7 can be prepared by synthetic methods such as those reviewed in "The Chemistry of Heterocyclic Compounds", Volume 14, John Wiley and Sons, or known to one skilled in the art. Scheme-7
IX Ih
Scheme-8 illustrates the preparation of compounds of Formula Ii from compounds of Formula X. The chemistry is analogous to that of Scheme-7.
Scheme-8
Ii
Example 1
Preparation of 5-Methyl-7-phenyl-2-(trifluoromethyl)- 1.2,4-triazolofl,5-a1pyrimidine
By the procedure reported by V. A. Lopyrev Zh. Obshch. Khim. 53 p. 1684, 1983 (Chemical Abstracts 99: 139865y, 1983) a crude sample of 3-amino-5-tri- fluoromethyl-1,2,4-triazole was prepared by the cyclocondensation. of -aminoguanidine bicarbonate with trifluoroacetic acid in refluxing toluene. This material was used effectively without further purification in subsequent ring condensation reactions.
To 30 ml. of glacial acetic acid stirring, 3.0g (19.7 mmol) of 3-amino-5-trifluoromethyl-1,2,4- triazole and 3.5g (21.6 mmol) of benzoylacetone were added and the mixture heated at reflux for 3h. A
solution- soon formed after heating. The solvent was evaporated in vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oily r si iip. Silica gel column chromatography ( ethylene chloride) afforded 3.09g of the title compound which was present as the major component, m.p. 106-108°C.
A minor regioisomer in which the phenyl and methyl groups on the desired product are reversed was also isolated (240 g. , m.p. 143-144°) from the chromatography.
Example 2 Preparation of 7-(3-Chlorophenyl)-5-methyl-2- (trifluoromethyl)-l,2.4-triazolori.5-alpyrimidine
To 10.Og (51.0 mmol) of 3 *-chloroacetophenone stirring in 100 ml of tetrahydrofuran/100 ml of diethyl ether and 20 ml of ethyl acetate, 4.0g of 50% sodium hydride oil dispersion was added portionwise with a certain amount of foaming. The reaction was stirred at ambient temperature overnight. Methanol (5.0ml) was added followed by 150 ml of water and 150 ml of diethyl ether. The aqueous layer was separated and acidified with 10% HC1 to pH -2-3. The aqeuous mixture was re-extracted with 200 ml of diethyl ether, the ether extract was washed with water (2X), brine, dried over magnesium sulfate, and evaporated in vacuo to give 11.6g of 3 '-chlorobenzoylacetone isolated as an oil. This oil was used directly in the next step without further purification.
To 5.0g (32.9 mmol) of 3-amino-5-trifluoro¬ methyl-1,2,4-triazole and 7.0g (36.0 mmol) 3 *-chlorobenzoyl- acetone in a round bottom flask, 50 ml of glacial acetic acid was added and the reaction heated at reflux 3h. The solvent was evaporated in vacuo to give a residue to which excess water and 200 ml of ethyl acetate was added. The organic layer was separated and washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oily residue to which a minimal amount of n-butylchloride was added. On standing, a solid precipitated which was filtered and washed with a small amount of n-butylchloride to give 2.2g of the title compound. The filtrate was concentrated in. vacuo to give an oil which was chromatographed on silica gel (methylene chloride followed by 3:1 ethyl acetate/-methylene chloride) to afford another 2.42g of the title compound, m.p. 115-116°C.
The minor regio isomer formed in this reaction where the phenyl and methyl groups are reversed was also isolated from the chromatography in a yield of 690 mg (m.p. 126-128°C).
Example 3 Prepration of 7-Phenyl-2-(trifluoromethyl)1,2,4- triazolori.5-alρyrimidine
A mixture of 3.0 ml of acetphenone and 4.0 ml of N,N-dimethylformamide dimethylacetal were heated neat at about 90° for 4h. After cooling, 4.0g (26.0 mmol) of 3-amino-5-trifluoromethyl-1,2,4-triazole and 70 ml of glacial acetic acid were added followed by heating at reflux 2h. The reaction mixture was
evaporated to dryness in vacuo and excess water and 200 ml of ethyl acetate added. The ethyl acetate layer was separated, washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromotagraphy afforded 1.4g of the title compound (m.p. 138-142°C). which was the major component present.
Example 4 Preparation of 5-Methγl-2-(methylthio)-7-phenyl- 1.2.4-triazolol " l,5-a1 yrimidine
To 50 ml of stirring glacial acetic acid, 2.5g (19.2 mmol) of 3-amino-5-methylthio-l,2, -triazole and 3.1g (19.1 mmol) of benzoylacetone was added followed by heating at reflux for 2h. The solvent was evaporated in vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Addition of n-butyl chloride resulted in crystallization of a solid which was filtered and washed with n-butyl chloride to give 1.33g of the pure title compound, 'm.p. 121-123°C.
Example 5
Preparation of 5-Methyl-2-(methylsulfonyl)-7-phenyl- 1,2.4-triazolo.l.5-a] yrimidine
To 2.6g (10.2 mmol) of 5-methyl-2-(methylthio)- 7-phenyl-l,2,4-triazolo[1,5-a] pyrimidine stirring in 30 ml of methylene chloride, 4.7g of 3-chloroperoxy
benzoic acid was added portionwise. The mixture was then stirred at ambient temperature for 45 minutes. Methylene chloride (150ml) was added and the solution washed with 10% sodium bisulfite, water, saturated sodium bicarbonate (2X) , brine, dried over magnesium sulfate and evaporated in vacuo to give an oily foam. Addition of n-butyl chloride to the foam resulted in crystallization of a solid which was filtered and washed with the same solvent to give 1.4g of the title compound, m.p. 158-159°C.
Example 6 Preparation of 2-Chloro-5-methyl-7-phenγl-
1.2,4-triazolon,5-a1pyrimidine
A mixture of 14g (141.4 mmol) of 3,5-diamino- 1,2,4-triazole and 24.Og (148.1 mmol) benzoylacetone was heated in 200 ml of glacial acetic acid at reflux for 2 hours. A solution soon formed after heating. The solvent was removed in vacuo and the residue dissolved in 400 ml of methylene chloride which was then washed with water (2X), brine and dried over magnesium sulfate. The solution was concentrated in vacuo (not to complete dryness) and ethyl acetate added to the residue. The precipitated solid was filtered and washed with ethyl acetate to give 16.Og of reasonably pure intermediate 5-methyl-7-phenyl- 1,2,4-triazσlo[l,5-a]pyrimidin-2-amine which was able to be taken on directly to the next step without further purification m.p. 246-250°.
To 2.0g (8.9 mmol) of 5-methyl-7-phenyl-l,2,4- triazolo[l,5-a]pyrimidin-2-amine stirring in 25 ml of concentrated hydrochloric acid, 1.2g (17.4 mmol) of sodium nitrite dissolved in 4.0 ml of water was added
dropwise at ambient temperature. After the addition, the reaction suspension was warmed at about 60° for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X) , saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 179-181°C.
Example 7 Preparation of 2-Bromo-5-methyl-7-phenyl- 1.2 " , 4-triazolori,5-a1 pyrimidine
A mixture of 7.0 g (71 mmol) 3,5-diamino- 1,2 ,4-triazole and 12.0 g (74 mmol) benzoylacetone in 100 ml of glacial acetic acid was heated at reflux 2 hours. After cooling, methylene chloride (200 ml) was added followed by the addition of excess water. The organic layer was separated, washed with water, brine, dried over magensium sulfate and evaporated in vacuo to give a solid residue to which ethyl acetate was added. Filtering gave 16.0 g of crude 5-methyl-7- phenyl-1, 2 , 4-triazolo[1, 5-a]pyrimidin-2-amine (m.p. 246-250°C) which was used directly in the next step. To 2.0g (8.9 mmol) of 5-methyl-7-phenyl-l, 2 , - triazolo[l, 5-a]pyrimidin-2-amine stirring in a mixture of 20 ml of 48% hydrobromic acid and 10 ml of glacial acetic acid, 2.0g (29.0 mmol) of sodium nitrite was slowly added portionwise with good
stirring at ambient temperature. The thick suspension was stirred at about 60°C for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X) , saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 178-180°C.
Example 8 Preparation of 5-methyl-7-phenyl-2-f(tri- fluό omethyl)thiol-1,2,4-triazolori,5-a1pyrimidine
A mixture of 10.0 g (86 mmol) 3-amino-5- mercapto-1,2,4-triazole and 14.0 g (86.5 mmol) of benzoylacetone in 100 ml of glacial acetic acid was heated at reflux 4 hours. Methylene chloride (500 ml) and excess water were added. The organic layer was separated and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a residue to which n-butyl chloride was added. Filtering gave 4.9 g of crude 5-methyl-7-phenyl-l,2, - triazolo[l,5-a]pyrimidin-2-thiol which was used directly in the next step.
To 1.5g (6.2 mmol) of 5-methyl-7-ρhenyl-l,2,4- triazolo[l,5-a]pyrimidin-2-thiol and 1.5g (10.9 mmol) of powdered potassium carbonate stirring in 20 ml of dimethylformamide, 3ml of condensed trifluoromethyl
iodide was added dropwise at ambient temperature. Keeping the dry ice condenser on from the addition, the stirred mixture was warmed to 30°C. At three separate times during a 2h period, 2.0 ml portions of trifluoromethyliodide were added. Excess water was added and the aqueous mixture was extracted with a 1:1 mixture of ethyl acetate/diethyl ether (200 ml) and the organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Silica gel column chromatography (methylene chloride followed by 1:1 methylene chloride/ethyl acetate) afforded 0.4g of the title compound (main component present), m.p, 91-93°C.
Example 9 5-methyl-7-(3-trifluoromethylphenyl)-2(trifluoro- methyl)-1.2,4-triazolori.5-alpyrimi ine
A mixture of 5.5g (23.9 mmol) of 3 '-trifluoro- methylbenzoylacetone (prepared by the same procedure as that shown in the beginning of Example 2 for the preparation of 3 'chlorobenzoylacetone) and 3. Og (19.7 mmol) 3-amino-5-trifluoromethyltriazole (prepared as reported in Example 1) were heated at reflux in 50 ml of glacial acetic acid for 2.5 h. The solvent was removed in vacuo and the resulting residue diluted with excess water and the aqueous mixture extracted with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, and dried over magnesium sulfate and evaporated in vacuo to give an oily residue.
A solid was triturated on addition of n-butyl- chloride/hexane and was filtered and purified by silica gel column chromatography (methylene chloride) to give 0.7g of the title compound, m.p. 133-134°C.
Example 10 Preparation of 5-methyl-7-phenyl-2- \ ( 2 .2.2-tri- fiuoroethoxy " .-1,2, -triazoloπ.5-a1pyrimidine
To 2.5 g (8.7 mmol) of 2-bromo-5-methyl- 7-ρhenyl-l,2,4-triazolo[l,5-a] yrimidine and 4.3 g of 2,2,2-trifluoroethanol stirring in 50 ml of THF, 0.4 g of sodium hydride (60% oil dispersion) was added portionwise with considerable foaming. The stirred reaction . mixture was heated at reflux 16 hours. After cooling, 5.0 ml of methanol of was added followed by the addition of 200 ml of ethyl acetate and excess water. The organic layer was washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give an oil. Trituration with n-butyl chloride/hexane and filtering afforded 1.4 g of the title compound (m.p. 103-104°C) .
Example 11
Preparation of 7-(3-chlorophenyl)-5-methγl-2-. (tri- fluoromethyl)thio1 l.2.4-triazoloQ,5-a1pyrimidine
A mixture of 10.0 g (51 mmol) of 3'-chloro¬ benzoylacetone and 6.0 g (52 mmol) of 3-amino- 5-mercapto-l,2,4-triazole in 100 ml of glacial acetic acid was heated at reflux 10 hours. The reaction mixture was concentrated in vacuo and 500 ml of methylene chloride and excess water added. The organic layer was separated and washed with water,
brine, dried over magnesium sulfate and evaporated in vacuo to give a solid residue to which n-butyl chloride was added. Filtration gave 6.2 g of crude 7-(3-chlorophenyl)-5-methyl-l,2,4-triazolo[l,5-a]- pyrimidin-2-thiol which was used directly in the next step.
To 5.6 g (20 mmol) of crude 7-(3-chlorophenyl)- 5-rnethyl-l,2,4-triazolo[1,5-a]pyrimidin-2-thiol and
2.0 g of potassium hydroxide in 100 ml of dioxane and 30 ml of water, 6.0 ml of trifluoromethyl iodide was added by way of a gas addition funnel equipped with a dry-ice condensor. The mixture was stirred at 60-70°C (keeping the dry-ice condensor on the reaction) under irradiation from a sunlamp for 2 hours. Ethyl acetate (300 ml) and excess water were added. The organic layer was separated and washed with water, brine, dried over magnesium sulfate, and evaporated in vacuo. The isolated residue was chromatographed on silica gel (3:1 followed by 1:1 hexane/ethyl acetate) to afford 2.5 g of the title compound, m.p. 95-96°C.
Example 12
Preparation of 7-(3-chlorophenyD-Tdifluoromethyl)- thiol-5-methyl-l,2.4-triazolori.5-a1 yrimidine
To 5.5 g (20.0 mmol) of crude 7-(3-chloro- phenyl)-5-methyl-l,2, -triazolo[1,5-a]pyrimi in-2-thio 1 and 2.7 g of potassium hydroxide stirring in a mixture of 150 ml of dioxane and 20 ml of water, 8.0 ml of chlorodifluoromethane was added by way of a gas addition funnel equipped with a dry-ice condensor. The mixture was heated at 60°C for 1.5 hours. Excess water and a 1:1 mixture of ethyl acetate and ethyl
ether was added. The organic layer was separated and washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (methylene chloride followed by 4:1 methylene chloride/ethyl acetate) to give 2.5 g of the title
C nmnnnnr., m, n 145—146°C.
Example 13
Preparation of 6-methyl-2-(trifluoromethyl)-8-
((3-trifluoromethyl) henyl)-imiάazoCl,2-blpy idazine
A solution of 3 g (12 mmol) of 6-methyl-4-
((3-trifluoromethyl)phenyl)-3-ρyridazinamine (prepared from 3'-trifluoromethylbenzoylacetone by the method of H. G . 0. Becker et al., Tetrahedron, 24, 2687 (1968)) and 2.5 g (13 mmol) of l-bromo-3,3,3-trifluoro-2-propanone in 75 ml of ethanol was refluxed for 16 hours. The solvent was removed with a rotary evaporator. The residue was dissolved in dichloromethane, was washed with saturated agueous sodium bicarbonate and was dried (sodium sulfate) . The solvent was removed with a rotary evaporator. The residue was purified by silica gel column chromatography to give 2.04 g of the title compound as a solid, m.p. 122-123°C.
Example 14
Preparation of 6-methyl-2-(trifluoromethyl)- 8-((3-trifluoromethyl)phenyl)-^ ri.2,4ltriazolori,5-b1 yridazine
To a slurry of 3.05 g (13 mmol) of Q-diphenyl- phosphinylhydroxylamine in 65 ml of chloroform was added 3.0 g (12 mmol) of 6-methyl-4-((3-trifluoro-
methyl)phenyl-3-ρyridazinamine. The mixture was stirred for 4 hours at room temperature, was refluxed for 2 hours and then was stirred at room temperature for 16 hours.
The solvent was removed with a rotary evaporator. A 100 ml portion of water was added to the residue. The pH was adjusted to 2 with 50% HI. The reaction mixture was filtered and the water was removed from the filtrate with a rotary evaporator to give 2.5 g of solid.
A 1.4 g portion of this solid was placed in a teflon-capped test tube and 5 ml of trifluoroacetic anhydride was added. The test tube was placed in an oil bath heated to 200°C for 15 minutes. After cooling, the residue was dissolved in dichloromethane and was washed with a saturated aqueous sodium . bicarbonate solution and was dried (sodium sulfate) . The solvent was removed with a rotary evaporator. The residue was purified by silica gel column chromatography to give 0.74 g of the title compound as a solid, m.p. 134-135.5°C.
Example 15
Preparation of 5-methyl-7-phenyl-2-(trifluoro¬ methyl)pyrazolo Q .5-al pyrimidin-3-carbonitrile
To a solution of 30 g (0.17 mole) of l, l-dicyano-2-chloro-2-trifluoromethylethylene
(prepared as taught by V. I. Krokhtyak et al., J, Orσ. Chem. (U.S.S.R), 1441 (1981)) in 300 ml of ether at 0°C was added 10.6 ml (0.33 mole) of hydrazine dropwise. The reaction waas stirred 30 minutes at room temperature. It was filtered and the solvent was removed with a rotary evaporator to give 28 g of a yellow semi-solid.
A 5.4 g (30 mmol) sample of this material was dissolved in 90 ml of ethanol and 5.0 g (30 mmol) of benzoylacetone was added. The reaction mixture was heated at reflux for 16 hours. It was cooled and the solvent was removed with a rotary evaporator. The residue was purified by silica gel column chrcrr.r. cgraphy to give 4.7 g of the title compound as a solid, m.p. 143-148°C.
Using the procedures outlined in Schemes 1-8 and Examples 1-15, the compounds of Tables I-VIII can be prepared.
TABLE T
R- R- E 4 E- R-
Me CF Me CH 2 Me CF-. Me CF Me CF-- Me CF : Me CF : Me CF ; Me CF, Me CF, Me CF ; Me CF, Me CF ; Me CF : Me CF : Et CF : Et CH : Et CF-
CF 3 H
Cl H
Br H
CN H
OCF 3 H
OCHF 2 H
OCH 2 CF 3 H
SCF 3 H
SCHF 2 H
S0 2 CF 3 H
CF 3 H
Cl H
Br H
CN H
OCF 3 H
OCHF 2 H
OCH 2 CF 3 H
SCF 3 H
SCHF 2 H
S0 2 CF 3 H
CF-, H H H H H H H
SCF 3 H SCHF 2 H S0 2 CF 3 H CF, H
R- 2-4 R.
Et SCF 3 Et SCF 3 Et SCF 3 Et SCF 3 Et SCF 3 Et SCF 3 Et SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Pr SCF 3 Me SCHF Me SCHF- Me SCHF- Me SCHF ; Me SCHF ; Me SCHF : Me SCHF : Me SCHF Me SCHF : Me SCHF Et SCHF : Et SCHF Et SCHF : Et SCHF-
Hi R- R. E-
CH 3 CO CF 3 H Cl H CH 3 C0 CF 3 H CF 3 H MeOCH- CF 3 H Cl H
CF 3 H CF 3 H F 2 CHO CF 3 H Cl H
FCH 2 CH 2 0 CF 3 H Cl H
CH 3 CH 2 CHC1 SCH 3
CH 2 =CH CF 3
CH 2 =CH CF 3 CH 2 =CH CHF 2
CH 2 =CH OCF 3
CH 2 =CH OCHF 2
CH 2 =CH OCH 2 CF 3
CH 2 =CH SCF 3 CH≡C CF 3
CH≡C CHF 2
CH≡C OCF 3
CH≡C OCHF 2
CH≡C OCH 2 CF 3 CH≡C SCF 3
CH≡C SCHF 2
CH 3 CH=CH CF 3
CH 3 CH=CH CF 3
CH 3 CH=CH SCF 3 CH 3 CH=CH CHF 2
CH 3 CH=CH OCF 3
CH 3 CH=CH OCH 2 CF 3
Me CF 3
Me CF 3 Me CF 3
Me CF 3
Me CF,
Bl
Me Me Me Me Me Me Me Me Me Me Et
TABLE II
B R, -1
Et Br CF 3
Et CF 3 OMe
Me CF 3 CF 3
Et CF 3 Cl
Me CF 3 H
Me CF 3 H
Et CF 3 H
MeSCH 2 CF 3 CF 3
Me Cl CF 3
Et OCH 2 CHF 2 CF 3
Me Cl CF 3
MeNH CF 3 CF 3
Me 2 N CF 3 CF 3
Me S0 2 CHF 2 CF 3
Me S0 2 CH 3 CF 3
Me CF 3 H n-propyl CF 3 H
Et CF 3 H
Et Cl H
Me SCHF 2 CF 3
Me CF 3 Br
HC≡C F 3 CF 3
Me F 3 • H
Me CF 3 Cl
Me CF 3 CF 3
Me CF 2 C1 CF
Et CHF 2 CF 2
FCH 2 CH 2 CF 3 CF ;
Me OCHF-, CF
Table III
l 2 E 7
Me CF 3 CF 3
Et CF 3 Cl
Me CF 3 H
Me CF 3 H
Et CF 3 H
MeSCH 2 CF 3 CF 3
Me Cl CF 3
Et 0CH 2 CHF 2 CF 3
Me Cl CF 3
MeNH CF 3 CF 3
Me 2 N CF 3 CF 3
Me S0 2 CHF 2 CF 3
Me S0 2 CH 3 CF 3
Me CF 3 H n-propyl CF 3 H
Et CF 3 H
Et Cl H
Me S SCCHF 2 CF 3
Me CF 3 Br
HC≡C CF 3 CF 3
Me F 3 H
Me CF 3 Cl
Me F 3 CF 3
Me CF 2 C1 CF 3
Et C CHHIF- CF 3
FCH 2 CH 2 CF 3 CF 3
Me OCHF 2 CF 3
Me OCH 2 CF 3 H Me CF 3 CF 3 Me CF 3 Cl Me CF, CF,
E l E 2 2^
Me CF 3 CF 3 H
Me CF 3 Cl H
Me OCF 2 H CF 3 H
Me OCF 2 H CF 3 H Me OCF 2 H Cl H
Me OCF 2 H Cl H
Me OCF 3 CF 3 H
Me OCF 3 CF 3 H
TABLE TV
Me CF 3 H H
Me CF 3 H H
Et CF 3 H H
Et CF 3 H H
H CF 3 H CN
Me SMe H H
Me Cl H H
Me SEt H H
Me CF 3 H H
Me OCH 2 CF 3 H CN
Me OCH 2 CF 3 H H
Me CF 3 H CN
Me CF 3 H CN
Me CF 3 F CN
Me CF 3 H Br
Et CF 3 H CN n-propyl CFn H CN
. o © ro
© σ.
00 O CN
H r-i o a z z κι fa CJ X X X X X X X X X X X X X X u a x c u x x u X a U z C z 2 J CJ CJ
Kl X X X X X X X fa X fa X X X X X X X X fa X X X X X X X X X X X X
X X X X X X X X ro ro ro ro X X X
ro ro ro ro ro ro ro ro ro Φ fa r-l fa fa fa fa fa fa fa fa a U CJ CJ CJ X X CJ CJ CJ CJ CJ CJ CJ U X CJ X X X J CJ O ro fa CJ CN CN
CN fa fa ro ro ro ro ro ro φ ro ro ro ro ro ro ro X ro ro X ro X ro ro ro ro ro
CN| fa fa fa fa fa fa S fa fa fa fa fa fa fa CJ fa fa rH rH CJ fa CJ fa fa fa fa U fa
Kl CJ CJ CJ CJ CJ CJ tO CJ CJ CJ CJ CJ CJ CJ CJ CQ o u u c cj cj co cj to cj cj cj cj m cj
E l E 2 7
Me CF, CF 3 Et CF : Cl Me CF- H Me H Et CF 3 H
MeSCH 2 CF 3 CF 3 Me Cl CF 3 Et OCH 2 CHF 2 CF 3 Me Cl CF 3 MeNH CF 3 CF 3 Me 2 N CF 3 CF 3 Me S0 2 CHF 2 F 3 Me S0 2 CH 3 CF 3 Me CF 3 H n-propyl CF 3 H Et CF 3 H Et Cl H Me SCHF 2 CF 3 Me CF 3 Br HC≡C CF 3 CF 3 Me CF 3 H Me CF 3 Cl Me CF 3 =CF 3 Me CF 2 C1 CF 3 Et CHF 2 CF 3
FCH 2 CH 2 CF 3 CF 3 Me OCHF 2 CF 3 Me 0CH 2 CF 3 H Me CF 3 CF : Me CF 3 Cl Me CF-, CF-
TABLE V
ι E 2 E 4 E=
E 4 E,
l E- E, E- R t
n-butyl CF 3 CF- H H
FCH 2 CF CF- H H F 2 CH CF Cl H H C1CH 2 CF Cl H H MeO CF Cl H H EtO CF- CF- H H Me OCHF 2 CF 3 H H Me SCHF 2 CF- H H Me SCHF 2 Cl H H Me CHF 2 CF- H H
Me CF 2 C1 CF- H H
Me CF 2 C1 Cl H H
MeOCH 2 CF 3 Cl H H
EtOCH- CF- CF- H H
F 2 CHO CF- Cl H H
FCH 2 0 CF- CF- H H
EtO CF 3 Br H H
Et SMe CF 3 H H
Et CF 3 H 3-NHS0 2 CF 3 H
Et CF. H 3-N0 2 H
Cl H H
Br H H
H H H H H F F F ?-a H
00 to cn o
o l- o ι^ lo- o tτ| x x o lij o ii) o it] o iτ) o
OJ 0J 0J 0J 00 00 to
X X X X
X X X X X X ^l X X X X X X
TABLE VI
R 1 R. E. R> R-
051 X X X X X X X fa X fa X X X X X X X X fa X X X X X X X X X X X X
ro fa φ u CN a CN a o o
CN ιn| u O CO
I I I CD 031 X X X ro X X X X X X X X X ro ro X X X X X X X X ro ro ro ro X X X
ro ro ro ro ro ro ro ro ro Φ rH fa rH fa fa fa fa fa fa fa fa a U U U U X X υ u u υ u u u υ x υ x x x u u o
CN CN fa fa ro ro ro ro ro ro Φ ro ro ro ro ro ro ro X ro X ro ro ro ro ro
CNl fa fa fa fa fa fa a fa fa fa fa fa fa fa C fa U fa fa fa fa U fa Kl u u u υ u u co u u υ u u u u u CQ U CQ U U U U m U
Me CF 3 CF 3
Et F 3 Cl
Me CF 3 H
Me CF 3 H
Et CF 3 H
MeSCH 2 CF 3 CF 3
Me Cl CF 3
Et OCH 2 CHF 2 CF 3
Me Cl CF 3
MeNH CF 3 CF 3
Me 2 N CF 3 CF 3
Me S0 2 CHF 2 CF 3
Me S0 2 CH 3 CF 3
Me CF 3 • H n-propyl CF 3 H
Et CF 3 H
Et Cl H
Me S SCCHF 2 CF 2
Me CF Br
HC≡C CF- CF :
Me CF- H
Me CF- Cl
Me CF- • CF :
Me CF 2 C1 CF :
Et CHF 2 CF
FCH 2 CH 2 CF CF-
Me OCH 2 CF 3 H
Me CF- CF ;
Me CF- Cl
Me CF- CF-
»
TABLE VII
Me CF 3 CF 2 H H H
Me CF 3 Cl H H H
Et CF 3 Cl H H H
Et CF 3 CF 2 H H H
H CF 3 CF 2 H H CN
Me SMe Cl H H H
Me Cl CF 2 H H H
Me SEt CF H H H
Me CF 3 H 3-SCF- H H
Me 0CH 2 CF 3 CF.. H H CN
Me 0CH 2 CF 3 CF, H H H
Me CF 3 CF, H H CN
Me CF 3 Cl H H CN
Me CF 3 CF, H F CN
Me CF 3 CF, H H Br
Et CF 3 CF, H H CN n-propyl CF. CF- H H CN
ro
© ro
© σ. oo CΛ
P CN
H O a a a a a a a
B 031 fa U X X X X X X X X X X X X X X u a x u u a x x u x u u u x u
031 X X X X X X X fa X fa X X X X X X X X fa X X X X X X X X X X X X
X X X X X X X X ro ro ro ro X X X
ro ro fa fa rH rH rH u u υ υ u co u
Φ Φ Φ 4J 4J Φ 4J a a a w w a w
CN
67
^ ϋ B
H H Me
H H C0 2 Me
3-OCH 2 CF 3 H CN
3-SCF 3 H CN
3-SCHF 2 H CN
H H CN
H H Cl
H H CN
H H CF 3
H H CN
H H CN
H H CN
H H CN
3-CN H CN
3-CN H CN
3-SMe H CN
3-CN H H
H H CN
H H CN
3-S0 2 CHF 2 H CN
3-C1 H CN
H H CN
H H CN
H H CN
H H CN
H H H
H H CONH 2
H H CONH 2 H H NO-,
Me CF 3 CF 3 H Me CF 3 Cl H Me OCF 2 H CF 3 H Me OCF 2 H CF 3 H Me OCF 2 H Cl H Me OCF 2 H Cl H Me OCF 3 CF 3 H
TABLE VI IT
70
CN fa
X φ u CN a a a a O r u u co u CO U I I I I I
(A X ro ro ro X X X X X X X X ro ro ro ro X X X ro ro X X X X X X X X
ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro fa fa fa fa fa fa fa fa fa U fa rH fa fa fa fa fa rH fa
0 Y31 1 U X X X U U U U U U U U X X x x u m u x u u u u u x u u u
CN fa ro X fa U CN rH U g fa U CN cN ro ro ro ro ro X X ro ro ro ro ro cN fa ro X ro ro ro oι| fa fa fa fa fa u U fa fa fa fa fa fa X fa U fa fa fa 031 u u u u u u o u co c u co u u u u u υ u υ o u υ υ
C
R- R- E 4 E- E- R-
Me CF 3 CF, H Me CF 3 Cl H Me OCF 2 H CF, H Me OCF 2 H CF, H Me OCF 2 H Cl H Me OCF 2 H Cl H Me OCF 3 CF, H
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 several 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 diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: Weight Percent*
Active Ingredient Diluent. s . Surfactant(s)
Wettable Powders 20-90 0-74 1-10
Oil Suspensions, 3-50 40-95 0-15
Emulsions, Solutions,
(including Emulsifiable
High Strength 90-99 0-10 0-2 Compositions
* 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¬ tured, 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, micro- biological 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, "Agglomeration", Chemical Engineering. December 4, 1967, pp. 147ff. and "Perry's Chemical Enqineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, 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 10 through 41;
R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 thro.ugh Col. 7, line 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, line 17 and Examples 1-4;
G. C. Klingman, "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 Hand¬ book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated.
Example A Wettable Powder 7-(3-chloroρhenyl)-5-methyl-2-(trifluoromethyl)-l,
2,4-triazolo[l,5-a] yrimidine 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13%
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, re- blended, and packaged.
Example B
Wettable Powder
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2,4-triazolo[l,5-a]pyrimidine 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46%
The ingredients are blended, coarsely hammer- milled and then air-milled to produce particles essen¬ tially all below 10 microns in diameter. The product is reblended before packaging.
Example C Granule
Wettable Powder of Example 11 5% attapulgite granules" 95%
(U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
Example D Extruded Pellet 7- (3-chlorophenyl)-5-me hy1-2-(trifluoromethyl )-l,
2,4-triazolo[l, 5-a] pyrimidine 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 E Low Strength Granule
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl )-l, 2 , 4-triazolo[l, 5-a] yrimidine 1% N,N-dimethylformamide 9% attapulgite granules 90%
(U.S.S. 20 to 40 sieve) The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
Example F Granule
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2, 4-triazolo [1, 5-a] pyrimidine 80%
wetting agent 1% crude ligninsulfonate salt (containing 10% 5-20% of the natural sugars) attapulgite clay 9%
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidiza- tion and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example G
Aqueous Suspension
7-(3-chlorophenyl)-5-methy1-2-(trifluoromethyl)-!, 2,4-triazolo[1, 5-a]pyrimidine 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% 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 essentially all under 5 microns in size.
Example H Hiαh Strength Concentrate
7-(3-chlorophenyl)-5-methy1-2-(trifluoromethyl)-l, 2,4-triazolo[l, 5-a]pyrimidine 99%
silica aerogel 0.5% synthetic amorphous silica 0.5% The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
Example I
Wettable Powder
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2, -triazolo[1, 5-a]pyrimidine 90% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 9.9%
The ingredients are blended and ground in a • hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
Example J Wettable Powder
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl ) -1 , 2, 4-triazolo[l, 5-a]pyrimi ine 40% sodium ligninsulfonate 20% montmorillonite clay 40%
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.
Example K Oil Suspension
7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-l, 2 ,4-triazolo [1, 5-a]pyrimidine 35%
blend of polyalcohol carboxylic 6% esters and oil soluble petroleum sulfonates xylene 59%
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.
Example L Dust
7-(3-chlorophenyl)-5-methy1-2-(trifluoromethyl)-l, 2, 4-triazolo[l, 5-a]pyrimidine 10% attapulgite 10%
Pyrophyllite 80%
The active ingredient is blended with attapul¬ gite and then passed through a hammer-mill to produce . particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.
Example M Oil Suspension
7-(3-chloroρhenyl)-5-methyl-2-(trifluoromethyl)-!, 2,4-triazolo[l, 5-a]pyrimidine 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic 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.
Test results indicate that compounds of the present invention are highly active preemergent and/or postemergent herbicides or plant growth regulants. Many of the compounds have utility for pre- and/or postemergence broad-spectrum grass and broadleaf weed control in areas where complete control of all vegetation is desired, such as around storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highways, and railroad structures, and in fallow crop areas. Some compounds have utility in crops such as barley (Hordeum spp.), corn (Zea spp.), cotton (Gossypium spp.), pea (Pisum spp.), peanut (Arachis spp.), rape (Brassica spp.), rice (Oryza spp.), sorghum (Sorghum spp.), soybean ( Glycine spp.), sugar beet (Beta spp.), sunflower (Helianthus spp.), triticale (Triticum-Secale spp.), and wheat (Triticum spp.). Some compounds are particularly useful for preemergence control of troublesome grass and selected small-seeded broadleaf weeds in barley, corn, cotton, rice, soybean, and wheat. In cereal crops such as barley, triticale, and wheat, some compounds are particularly useful for preemergence control of grass weeds such as blackgrass (Alopecurus myosuroides ) , foxtail (Setaria spp.), and wild oat (Aυena fatua) , and selected broadleaf weeds such as kochia (Kochia scoparia) , lambsquarters (Chenopodium album ) , and wild buckwheat (Polygonum convolvulus) . In rice, some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli ) . In cotton, some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli ) , bermudagrass (Cynodon dactylon ) , panicum (Panicum spp.), goosegrass
(Eleusine spp.), crabgrass (Digitaria spp.), and pigweed (Amaranthus spp. ) . In addition, many compounds of this invention are useful for the control of weeds in plantation crops such as banana, citrus crops, cocoa, coffee, palm, rubber, sugar cane, etc. Several of these compounds are also useful for weed control in fruit crops such as cranberries, apples, pears, cherries, etc. Several compounds of this invention are particularly useful for the control of troublesome grass weeds in sugar cane (Saccharum spp.). Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for compounds of this invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types .of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.004 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required, such as a herbicide for fallow land. Preferred rates of application are from 0.025 to 2.0 kg/ha. One skilled in the art can easily determine the application rate needed for the desired level of weed control.
The compounds of the invention may be used in combination with any other commercial herbicide, representative examples of which are those of the sulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether, carbamate, imidazolinone, cineole and bipyridylium types. A partial listing follows:
Common Name Chemical Name
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-diethy1phenyl)- N-(methoxy-methyl)acetamide
ametryn N-ethyl-N'-(l-methylethyl)-6-
(methylthio)-l,3,5-triazine-2,
4-diamine
amitrole 1H-1,2,4-triazol-3-amine
AMS ammonium sulfamate
asulam methyl [ (4-aminophenyl) sulfonyl ] carbamate
atrazine 6-chloro-N-ethyl-N'-(l-methyl ethyl)-l,3,5-triazine-2, 4-diamine
barban 4-chloro-2-butynyl 3-chloro carbamate
benefin N-butyl-N-ethyl-2 , 6-dindtro-4- (tri-fluoromethyl)benzena ine
84
Common Name Chemical Name
bensulfuron 2-[ [ [[ [(4,6-dimethoxy-2-pyrimi methyl dinyl)amino]-methylcarbonyl]amino] sulfonyl]methyl]benzoic acid, methyl ester
υcn-iuiiue 0,0-bis(l-methylethyl) S-[2- [(phenylsulfonyl)amino]ethyl] phosphorodithioate
bentazon 3-(l-methylethyl)-(lH)-2,l,3- benzothia-diazin-4(3H)-one, 2,2-dioxide
benzofluor N-[4-(ethylthio)-2-(trifluoro methy1)-phenyl]methanesuIfona mide
benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)- DL-alanine
bifenox methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoate
bromacil • 5-bromo-6-methyl-3-(1-methyl propyl)-2,4(IH,3H)pyrimidinedione
bro oxynil 3,5-dibromo-4-hydroxybenzonitrile
butachlor N-(butoxymethyl)-2-chloro-N-(2,6- diethyl-phenyl)acetamide
Common Name Chemical Name buthidazole 3-[5-(l,l-dimethylethyl)-l,3,4-thia- diazol-2-yl]-4-hydroxy-l-methyl-2- imidazolidinone butralin 4-(l, l-dimethylethyl)-N-(l-methyl- propyl)-2 , 6-dinitrobenzenamine butylate S-ethyl bis(2-methylpropyl)carbamothioate cacodylic dimethyl arsinic oxide acid
CDAA 2-chloro-N,N-di-2-propenylacetamide
CDEC 2-chloroallyl diethyldithioca bamate chloramben 3-amino-2 , 5-dichlorobenzoic acid chlorbromuron 3-(4-bromo-3-chlorophenyl)-l-methoxy-l- methylurea chlorimuron 2-[ [ [ [ (4-chloro-6-methoxy-2-pyrimidinyl)- ethyl amiho]carbonyl] amino] sulfonyl]benzoic acid, ethyl ester chloroxuron N'-[4-(4-chlorophenoxy)phenyl] -N,N- dimethylurea chlorpropham 1-methylethyl 3-chlorophenylcarbamate chlorsulfuron 2-chloro-N-[ [ (4-methoxy-6-methyl-l, 3 , 5- triazin-2-yl) amino]carbonyl] enzene- sulfonamide chlortoluron N'-(3-chloro-4-methylphenyl)-N,N- dimethylurea cinmethylin exo-1-methy1-4-(1-methylethyl)-2- [ (2- methylphenyl)methoxy]-7-oxabicyclo- [2.2. l]heptane clethodim (E,E)-(±)-2-[l-[ [ (3-chloro-2-propenyl)- oxy] imino]propyl]-5-[2-(ethylthio)- propyl] -3-hydroxy-2-cyclohexen-l-one
86
Common Name Chemical Name
clomazone 2-[ (2-chloroρhenyl)methyl]-4 ,4-dimethyl- 3-isoxazolidinone cloproxydim (E,E)-2-[l-[ [ (3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-1-one clopyralid 3 , 6-dichloro-2-pyridinecarboxylic acid
CMA calcium salt of MAA cyanazine 2-[ [4-chloro-6-(ethylamino)-l,3 , 5-tri- azin-2-yl] amino]-2-methylproρanenitrile cycloate S-ethyl cyclohexylethylcarbamothioate cycluron 3-cyclooctyl-l, 1-dimethylurea cyperquat l-methyl-4-phenylpyridinium cyprazine 2-chloro-4-(cycloproρylamino)-6-(iso- propylamino)-≤.-triazine cyprazole N-[5-(2-chloro-l,l-dimethylethyl)-l,3,4- thiadiazol-2-yl]eyelopropanecarbox- amide cypromid 3 ' ,4 '-dichlorocyclopropanecarbσxanilide dalapon 2 , 2-dichloroproρanoic acid dazomet tetrahydro-3 , 5-dimethyl-2H-l,3 , 5-thia- diazine-2-thione
DCPA dimethyl 2,3,5, 6-tetrachloro-l,4-benzene- dicarboxylate desmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyl]carbamate desmetryn 2-(isopropylamino)-4-(methylamino)-6- (methylthio)-s_-triazine diallate S-(2,3-dichloro-2-propenyl)bis (1- methylethyl)carbamothioate
87
Common Name Chemical Name dicamba 3 , 6-dichloro-2-methoxybenzoic acid dichlobenil 2,6-dichlorobenzonitrile dichlorprop (±)-2-(2 , 4-dichlorophenoxy)propanoic acid dichlofop (±)-2-[4-(2, 4-dichlorophenoxy) phenoxy] - propanoic acid diethatyl N-(chloroacetyl)-N-(2 , 6-diethylphenyl)- glycine difenzoquat 1, 2-dimethy1-3 , 5-diphenyl-lH-pyrazolium dinitramine N 3 ,N 3 -diethy1-2,4-dinitro-6-(trifluoro¬ methyl)-!, 3-benzenediamine dinoseb 2-(l-methylpropyl)-4 , 6-dinitroρhenol diphenamid N,N-dimethyl-α-phenylbenzeneacetamide dipropetryn 6-(ethylthio)-N,N' -bis(1-methylethyl)- 1,3, 5-triazine-2 , 4-diamine diquat 6,7-dihydrodipyrido[l, 2-a:2' ,l'-c]- pyrazinedium ion diuron ' -(3 , 4-dichlorophenyl) -N,N-dimethylurea
DNOC 2-methyl-4 , 6-dinitrophenol
DPX-M6316 3-[ [ [ t (4-methoxy-6-methyl-l, 3,5-triazin- 2-yl) amino] carbonyl] amino] sulfonyl]- 2-thiophenecarboxylic acid, methyl ester
DSMA disodium salt of MAA endothall 7-oxabicyclo[2.2.1]heptane-2 , 3-dicarbox- ylic acid
EPTC S-ethyl dipropylcarbamothioate ethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2 , 6- dinitro-4-(trifluoromethyl)- benzenamine
Common Name Chemical Name ethofumesate (±)-2-ethoxy-2 ,3-dihydro-3 , 3-dimethyl- 5-benzofuranyl methanesulfonate
Express® 2-[ [ [[N-(4-methoxy-6-methyl-l,3, 5-triazine- 2-yl)-N-methylamino]carbonyl] amino]- sulfonyl]benzoic acid, methyl ester 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 flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)- DL-alanine fluazifop (±)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid fluchloralin N-(2-chloroethyl)-2, 6-dinitro-N-propyl- 4-(trifluoromethyl)benzenamine fluometuron N,N-dimethyl-N'-[3-(trifluoromethyl)- phenyl]urea fluorochlor- 3-chloro-4-(chloromethyl)-l-[3-(trifluoro- i one methyl)phenyl]-2-pyrrolidinone fluorodifen p_-nitrophenyl α,α,α-trifluoro-2-nitro- p_-tolyl ether fluoroglycofen carboxymethyl 5-[2-chloro-4-(tri- fluoromethyl)phenoxy]-2-nitrobenzoate fluridone l-methyl-3-phenyl-5-[3-(trifluoro¬ methyl)phenyl]-4(IH)-pyridinone fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy] N-(methylsuIfonyl)-2-nitrobenzamide
89
Common Name Chemical Name 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 hexazinone 3-cyclohexyl-6- (d methyl amino ) -l-methyl- 1 , 3 , 5-tri azine-2 , 4 ( lH, 3H) -dione imazamethabenz 6-(4-isopropyl-4-methyl-5-oxo-2- imidazolin-2-yl)- -toluic acid, methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)- E-toluic acid, methyl ester imazapyr (±) -2-[4,5-dihydro-4-methy1-4-(1-methyl¬ ethyl)-5-oxo-lH-imidazo1-2-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-ρyridinecarboxylic acid ioxynil 4-hydroxy-3,5-diiodobenzonitrile isopropalin 4-(1-methylethyl)-2,6-dinitro-N,N- dipropylbenzenamine isoproturon N-(4-isopropylphenyl)-N' ,N'-dimethylurea isouron N'-[5-(l,l-dimethylethyl)-3-isoxazolyl]- , -dimethylurea isoxaben N-[3-(l-ethyl-l-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamide karbutilate 3-[ [(dimethylamino)carbonyl]amino]- phenyl-(1,1-dimethylethyl)carbamate
Common Name Chemical Name lactofen (±)-2-ethoxy-l-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoate lenacil 3-cyclohexyl-6,7-dihydro-lH-cyclopenta- pyrimidine-2, (3H,5H)-dione linuron N'-(3,4-dichlorophenyl)-N-methoxy-N- methylurea
MAA methylarsonic acid MAMA monoammonium salt of MAA MCPA (4-chlσro-2-methylphenoxy)acetic acid MCPB 4-(4-chloro-2-methylphenoxy)butanoic acid mecoprop (±)-2-(4-chloro-2-methylρhenoxy)- propanoic acid mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)- sulfonyl]amino] henyl]acetamide methal- N-(2-methyl-2-propenyl)-2, 6-dinitro-N- propalin propy1-4-(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 methoxuron N'-(3-chloro-4-methoxyphenyl)-N,N- dimethylurea metolachlor 2-chloro-N-(2-ethyl-6-methylρhenyl)-N- (2-methoxy-1-methylethyl)acetamide
Common Name Chemical Name metribuzin 4-amino-6-(l, 1-dimethylethyl)-3-(methyl- thio)-l,2,4-triazin-5(4H)-one metsulfuron 2-t [ [ [ (4-methoxy-6-rnethyl-l,3,5-tri- methyl azin-2-yl) amino]carbonyl] - amino] sulfonyl]benzoic acid, methyl ester
MH 1,2-dihydro-3 , 6-pyridazinedione molinate S-ethyl hexahydro-lH-azeρine-1-carbo- thioate monolinuron 3-(p_-chlorophenyl)-l-methoxy-l-methyl- urea monuron N' -(4-chlorophenyl)-N, N-dimethylurea monuron TCA Salt of monuron and TCA MSMA monosodium salt of MAA napropamide N,N-diethyl-2-(l-naρhthalenyloxy)- propanamide naptalam 2-[ (1-naphthalenylamino)carbonyl] - benzoic acid neburon l-butyl-3-(3 , 4-dichlorophenyl)-l-methyl- urea nitralin 4-(methylsulfonyl)-2, 6-dinitro-N,N- dipropylaniline nitrofen 2 , 4-dichloro-l-(4-nitrophenoxy) benzene nitrofluorfen 2-chloro-l-(4-nitrophenoxy)-4-(tri- fluoromethy1)benzene norea N,N-dimethyl-N' -(octahydro-4 , 7-methano- lH-inden-5-yl)urea 3aα,- 4α,5α,7α,7act-isomer norflurazon 4-chloro-5-(methylamino)-2-[3-(trifluoro- ethyl)phenyl]-3(2H)-pyri azinone
92
Common Name Chemical Name oryzalin 4-(dipropylamino)-3,5-dinitro- benzenesulfonamide oxadiazon 3-[2,4-dichloro-5-(l-methylethoxy)- phenyl]-5-(l,1-dimethylethyl)-
1,3,4-oxadiazol-2(3H)-one oxyfluorfen 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene paraquat 1,l'-dimethyl-4,4'-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(1-ethylproρyl)-3,4-dimethyl-2,6- dinitrobenzenamine perfluidone 1,1,1-trifluoro-N-[2-methyl-4-(phenyl- sulfonyl) henyl]methanesuIfonamide phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamate • picloram 4-amino-3,5 ,6-trichloro-2-pyridine- carboxylic acid
PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl ester procyazine 2-[[4-chloro-6-(cyclopropylamino)-1,3,5- triazine-2-yl]amino]-2-methylpropane- nitrile profluralin N-(cyclopropylmethyl)-2,6-dinitro-N-propyl ( rifluoromethyl)benzenamine prometon 6-methoxy-N,N'-bis(1-methylethyl)-1,3,5- triazine-2 ,4-diamine rome ryn N, '-bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamine pronamide 3 ,5-dichloro-N-(1,l-dimethyl-2-proρyn- yl)benzamide
Common Name Chemical Name propachlor 2-chloro-N-(1-methylethyl)-N- phenylacetamide propanil N-(3,4-dichloroρhenyl)ρropanamide propazine 6-chloro-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine propham 1-methylethyl phenylcarbamate prosulfalin N-[ [4-(dipropylamino)-3, 5-dinitro- phenyl]sulfonyl]-S,S-dimethylsulfi1- imine prynachlor 2-chloro-N-(l-methyl-2-propynyl)acet- anilide pyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinone quizalofop (+)-2-[4-[(6-chloro-2-quinoxalinyl)- ethyl oxy]phenoxy] ropanoic acid, ethyl ester secbumeton N-ethyl-6-methoxy- '-(1-methylpropy1)- 1,3,5-triazine-2,4-diamine sethoxydim 2-[l-(ethoxyimino)butyl]-5-[2-(ethyl- thio)proρyl]-3-hydroxy-2-cyclohexen- 1-one siduron N-(2-methylcyclohexyl)-N'-phenylurea simazine 6-chloro-N,N'-diethyl-l,3,5-triazine- 2,4-diamine 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)-1,3,4-thiadi- azol-2-yl]-N,N'-dimethylurea terbacil 5-chloro-3-(l,l-dimethylethyl)-6- methyl-2,4(IH,3H)-pyrimidinedione
94
Common Name Chemical Name terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(l,l- dimethylethyl)-6-methylphenyl]- acetamide terbuthyl- 2-(i≤xi.-butylamino)-4-chloro-6-(ethyl- azine amino)-s_-triazine
2,6-di-ie_r£-butyl-p_-tolyl methylcar- bamate terbutryn N-(l,l-dimethylethyl)-N * -ethyl-6- (methylthio)-l,3,5-triazine- 2,4-diamine thiobencarb S-[(4-chlorophenyl)methyl] diethylcar- bamothioate triallate S-(2,3,3-trichloro-2-propenyl) bis(l- methylethyl)carbamothioate triclopyr [(3,5,6-trichloro-2-ρyridinyl)- oxy]acetic acid tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2- trichloroethyl)oxirane trifluralin 2,6-dinitro-N,N-dipropyl-4-(tri- fluoromethyl)benzenamine trimeturon l-(jD-chloroρhenyl)-2,3,3-trimethylpseu- dourea
2,4-D (2,4-dichlorophenoxy)acetic acid 2,4-DB 4-(2,4-dichlorophenoxy)butanoic acid vernolate S-propyl dipropylcarbamothioate xylachlor 2-chloro-N-(2,3-dimethylρhenyl)-N- (1-methylethyl)acetamide
The herbicidal properties of the subject com¬ pounds were discovered in a number of greenhouse tests The test procedures and results follow.
TABLE OF COMPOUNDS
OS0 2 CF 3 Cl H H 131-133
CF 3 Cl H H 96-98
CF 3 H 3-N0 2 H 206-208
CF 3 Cl H H 66-69
CF 3 CF 3 H H 91-94
CF 3 CF 3 H H 54-56
CF 3 Br H H 95-99
CF 3 H 3-CN H 185-189
CF 3 CF 3 H H 66-69 CF 3 H H F 99.5-10 F 3 CF 3 H H 72-74 CF 3 CF 3 H H 120-124
CF 3 H 3-OCF- H 115-117
CF 3 CF 3 H H ' 183-185
CF 3 CF 3 H H 158-160
CF 3 CF 3 H H 142-145
CF 3 Br H H 116-118 SMe CF 3 H H 173-175
OCH 2 CHF 2 CF 3 H H 136-137
0CH(Me)CF 3 CF 3 H H 177-178
CF 3 Cl 3-C1 H 185-190
CF 3 Cl H H 86-88
CF 3 H 3-OPh H 167-170
CF 3 H 3-CN H 109-110
CF 3 H 3-CN H 164-167 F 3 H 3-NMe 2 H 88-90
CF 3 H 3-OCHF- H 103-105 CF 3 H 3-SMe H 95-100
CF 3 H 3-Ph H 165-173 CF H 3-OCHF- H 96-99
£ 2 R 4 m. p
CF 3 2-F H 112- • 115 F 3 H H 191 •194 CF 3 H H 215- ■ 218
CF 3 2-F H 103 •106
CF 3 H H 77 -79
CF 3 H H 96 -99
SCH ; H H 202 -204
CF 3 H H oil
CF 3 H H 93 ■ 95
CF 3 H H 63 • 68
Br H H 90 •92
CF, H H 136 -140
OCH 2 CF 3 CF 3 H H 77 •80
CF 3 CF 2 CF 3 H H 146 -149
CF 3 SCF 2 CF 3 H H oil
CF 3 S0 2 CF 2 CF 3 H H wax
Br Br H H 132 -135
OCH 2 CF 3 Br H H 93 -95
CF 3 Cl 2-OCH 3 H 102 -105
CF 3 CF 3 6-F H 85 -89
Br OCF- H H 126 -129
Br Cl H H 130 -133
OCH 2 CF 3 OCF- H H 144 -143
OCH 2 CF 3 Cl H H oil
OCH 3 CF- H H 173 -174 OCHF- CF- H H 102
CF 3 F 3 OCH 2 CF 3 F 3 CF.
E
CF 3 CF 2 CF Ξ CF 3 CF~ CF ; CF, CF- CF-
TEST A
Seeds of barley ( ordeum vulgar ) , barnyardgrass (Echinochloa crus-galli) , cheatgrass (Bromus secalinus) , cocklebur (Xanthium pensylvanicum ) , corn (Zea mays ) , cotton (Gossypium hirsutum ) , crabgrass (Digitaria spp.), giant foxtail (Setaria faberi ) , morningglory (Ipomoea spp. ) , rice (Oryza sativa ) , sorghum (Sorghum bicolor) , soybean (Glycine max) , sugar beet (Beta vulgar is) , velvetleaf (Abutilon theophι ~ asti) , wheat ( Triticum aestivum ) , and wild oat (Avena fatua ) and purple nutsedge ( Cyperus rotundus ) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytoto-xic 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 (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately sixteen days, after which all species were compared to controls and visually evaluated. The 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
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 (2000g/ha) POSTEMERGENCE
Barley - - 4 0 3 0 0 9 0 0 2 0 1 0 8 1 7 0 0 2 0 0
Barnyardgrass 0 0 6 0 9 0 0 - 0 0 9 2 8 1 9 5 - 0 0 7 0 0 Cheatgrass 0 0 0 0 7 0 0 8 0 0 2 0 2 0 8 2 8 0 0 2 0 0 Cocklebur 2 3 5 1 8 3 2 8 2 0 6 1 7 3 6 4 8 0 1 6 1 2 Corn 0 0 4 0 6 0 0 9 0 0 7 0 7 0 8 6 7 0 0 6 0 0
Cotton 2 6 7 2 9 9 7 10 4 0 7 1 10 7 10 9 10 0 1 9 0 0 Crabgrass 0 6 7 3 7 2 2 9 0 0 10 0 8 2 9 8 - 0 0 8 1 0 Giant Foxtail - - 7 0 9 0 0 9 0 0 8 0 8 2 9 6 9 0 0 5 2 0 Morningglory 5 5 7 5 8 3 6 9 5 0 7 2 9 3 9 8 9 1 2 3 6 1 Nutsedge 0 0 4 0 7 0 0 9 0 0 2 0 5 0 6 3 7 0 0 - 0 0 Rice 0 0 3 1 8 1 0 9 0 0 5 2 8 0 8 3 8 0 0 5 1 0
Sorghum 0 0 2 0 7 1 0 9 0 0 2 0 5 0 7 0 7 0 0 2 0 0 Soybean 3 8 7 3 8 8 2 9 7 3 9 2 9 4 9. 9 9 0 6 9 6 6 Sugar beet 5 2 7 3 9 8 3 9 5 0 8 2 9 3 10 8 9 0 7 9 8 5 Velvetleaf 2 1 4 1 8 2 0 9 1 0 8 0 8 2 7 1 7 0 1 7 3 1 Wheat 0 0 3 0 3. " 0 0 8 0 0 0 0 1 0 7 1 7 0 0 1 0 0 Wild oat 0 0 3 0 7 0 0 9 0 0 3 0 6 0 9 4 7 0 0 6 0 0 PREEMERGENCE
Barley - - 0 0 9 0 0 8 0 0 8 0 8 0 7 4 7 0 0 0 0 0
Barnyardgrass 9 8 9 0 9 0 0 10 7 0 10 0 10 0 10 9 10 0 8 10 4 0 Cheatgrass 5 2 7 0 3 0 0 9 2 0 8 0 10 0 9 2 9 0 0 3 0 0
Cocklebur 2 3 0 0 0 0 2 8 1 0 3 0 6 0 5 2 4 0 0 0 1 0
Corn 4 6 5 0 9 0 0 9 4 0 8 0 7 0 7 5 7 0 0 2 0 0
Cotton 0 0 0 0 2 0 0 6 0 0 0 0 0 0 7 2 5 0 0 0 0 0
Crabgrass 9 8 10 3 9 8 0 10 9 0 10 0 10 0 10 10 10 3 9 10 9 5
Giant Foxtail - - 10 3 9 2 0 10 10 0 10 5 10 0 10 10 10 0 10 8 10 6 Morningglory 9 10 10 0 10 8 8 10 10 0 10 1 10 1 10 10 10 0 9 7 10 8
Nutsedge 2 3 0 0 3 0 0 7 4 0 5 0 9 - 8 - 3 0 0 0 0 0 6
Rice 2 3 7 0 5 0 0 9 1 0 5 0 4 0 6 5 7 0 0 4 0 0 8
Sorghum 1 2 7 0 9 0 0 10 3 0 9 0 10 0 8 6 9 0 0 5 0 0 1
Soybean 5 7 9 0 9 0 0 9 8 3 8 1 9 2 9 9 8 0 8 8 8 8 9
Sugar beet 5 10 10 0 10 3 4 10 10 0 10 5 10 0 10 9 10 0 9 10 9 8 1
Velvetleaf 2 4 10 0 10 6 1 10 9 0 7 0 10 0 10 9 10 0 5 10 7 3 1
Wheat 1 0 2 0 5 0 0 9 0 0 5 0 3 0 6 3 7 0 0 1 0 0 8
Wild oat 8 2 7 0 6 0 0 9 1 0 7 0 10 0 10 3 10 0 0 7 0 0 9
TABLE A COMPOUND
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 59 60 61 62 63 64 (2000g/ha) POSTEMERGENCE
TABLE A COMPODND
65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 94 95 96
( 2000g/ha) POSTEMERGENCE
TABLE A COMPOUND
43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 (400g/ha)
POSTEMERGENCE
TABLE A COMPOOND
75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 94 95 96 97 98 99 100 101 102 103 104 105 (400g/ha) POSTEMERGENCE
rr o o o o o o o
3 t-f o o o αι o y- 3
σ. o σ
TEST B
Seeds of barley (Hordeum vulgare) , barnyardgrass (Echinochloa crus-galli) , blackgrass (Alopecurus myosuroides), chickweed ( Stellar ia media) , cocklebur (Xanthium pensylvanicum) , corn (Zeamays) , cotton (Gossypium hirsutum) , crabgrass (Digitaria spp.), downy brome (Bromus tectorum) , giant foxtail (Setaria faberi) , σrppn foxtail (Setaria viridis) , jimsonweed (Datura stramonium) , johnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , morningglory (Ipomoea spp.), rape (Brassica napus) , rice (Oryza sativa) , sicklepod (Cassia obtusifolia) , soybean (Glycine max), sugar beet (Beta vulgaris) , teaweed (Sida spinosa) , velvetleaf (Abutilon theophrasti) , wheat (Triticum aestivum) , wild buckwheat (Polygonum convolvulus) , and wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) 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 (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. Preemergence and postemergence application rates for each compound are listed in Table B. Plant response ratings, summarized in Table B, 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 B CCMPOϋHD
13 28 43 44 45 75 104
(lOOOg/ha) POSTEMEHGEHCK
TABLE B COMPOUND
3 8 15 16 17 23 25 28 32 33 34 35 36 37 40 43 44 46 48 (125g/ha) POSTEMERGENCE
Barley 0 2 0 0 0 2 1 0 0 0 0 0 2 1 0 0 0 2 0
Barnyardgrass 0 7 8 0 3 5 8 0 3 3 0 2 9 1 0 0 3 3 9
Blackgrass 0 2 8 0 2 8 9 0 2 0 0 0 3 0 0 0 3 3 2
Chickweed 0 3 2 0 2 9 5 0 6 2 0 - 10 6 7 0 3 3 7
Cocklebur 0 2 0 0 2 3 2 0 6 3 0 3 7 5 6 4 0 3 5
Corn 0 2 1 0 2 0 0 0 0 0 0 0 2 2 2 0 0 2 1
Cotton 0 1 4 0 3 2 0 0 5 0 0 4 4 8 7 1 4 3 8
Crabgrass 0 3 9 2 0 8 8 10 3 3 2 1 8 6 6 6 5 3 2
Downy bro e 0 0 2 0 0 2 0 0 0 0 0 0 0 0 0 0 0 2 0
Giant foxtail 0 5 7 0 0 7 9 0 7 6 0 0 10 3 0 - 3 9 6
Green foxtail 0 6 9 0 2 8 8 0 - 5 0 3 9 3 1 0 0 5 5
Jimsonweed 0 5 10 0 0 10 10 2 10 5 3 10 10 8 9 5 5 10 10
Johnsongrass O 2 2 O O 3 2 O - 0 O O 2 O 0 4 3 - 2
Lambsquarters 0 8 10 '2 5 9 9 2 10 6 3 10 10 10 10 6 7 10 10
Morningglory 0 - 7 2 2 0 8 2 5 5 0 5 2 2 1 - 3 7 5
Nutsedge O 2 0 0 O 2 3 O 0 2 O 0 0 O 0 O - O O
Rape 0 7 8 0 2 9 9 2 - 6 2 10 10 8 8 5 4 10 6
Rice 0 2 2 0 0 2 2 0 0 0 0 0 2 3 1 - 0 4 2
Sicklepod 0 3 3 0 3 2 3 0 9 2 0 4 8 2 8 2 3 9 5
Soybean 3 7 7 4 3 3 9 0 5 3 .2 4 5 7 5 4 4 6 5
Sugar beet 0 8 10 0 9 10 9 0 9 10 8 10 10 10 10 8 8 10 10
Teaweed 0 0 3 0 0 2 5 0 3 3 0 4 4 4 - 0 3 0 6
Velvetleaf 0 3 2 2 5 6 7 - 0 0 0 1 4 5 6 0 3 8 5
Wheat 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1
Wild buckwheat 0 5 - - 3 10 9 0 10 9 0 - 10 10 6 10 4 7 0
Wild Oat 0 1 2 0 1 3 3 0 0 0 0 0 2 1 0 0 0 3 1
Johnsongrass 0 1 0 0 0 0 0 8 0 0 0 . - 0 0 - 0 8
Lambsquarters 8 5 8 0 2 8 8 10 5 0 8 10 9 10 9 9 7
Morningglory - - 7 2 0 - 8 5 5 0 3 0 - 1 5 - 6
Nutsedge 0 0 0 0 0 0 2 0 0 0 0 0 - 0 0 0 0
Rape 4 3 7 0 0 8 9 10 5 0 6 10 8 8 5 - 7
Rice 0 0 0 0 0 0 0 0 0 0 0 0 3 1 2 1 0
Sicklepod 4 0 0 0 2 2 3 6 - 0 2 5 1 - 8 5 3
Soybean 4 7 6 3 2 3 9 5 2 0 4 4 6 5 4 4 6
Sugar beet 7 6 10 0 8 10 9 4 10 5 10 10 10 10 10 10 9
Teaweed 3 0 0 0 0 0 2 3 3 0 4 3 3 4 0 5 0
Velvetleaf 3 3 0 0 3 4 5 0 0 0 0 0 4 6 3 4 -
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild buckwheat 5 3 - - 0 8 5 5 3 0 0 8 9 3 7 0 10
Wild Oat 0 0 1 0 0 2 0 0 0 0 0 0 0 0 2 1 0
Johnsongrass 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0
Lambsquarters 5 0 7 5 8 3 0 3 10 9 9 4 4 4 10 10 7 4 9 0
Morningglory - 0 0 7 0 0 0 0 - - - 6 3 3 10 6 7 5 4 0
Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 -
Rape 0 0 7 8 9 3 0 5 10 6 4 2 5 3 4 7 7 4 3 0
Rice 0 0 0 0 0 0 0 0 0 0 1 0 0 0 2 0 0 1 0 0
Sicklepod 0 0 0 0 4 - 0 0 5 1 4 3 3 - 6 3 5 4 4 1
Soybean 6 0 3 9 2 2 0 3 3 5 4 4 4 3 3 6 5 5 0 2
Sugar beet 6 7 10 8 0 9 5 10 10 10 9 8 10 5 10 6 7 10 10 2
Teaweed 0 0 0 0 2 0 0 0 3 3 4 0 0 0 8 5 3 0 3 0
Velvetleaf 3 0 0 2 0 0 0 0 0 - 4 0 6 5 5 3 6 3 3 1
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild buckwheat 0 0 7 5 4 3 0 0 5 2 0 4 10 7 3 7 6 - 4 0
Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 2 0
TAB LB ςcM p qqND
5 8 9 13 15 16 17 23 25 28 32 33 34 35 36 37 40 43 44 45 46 48 (250g/ha) PREEMERGENCE
Barley 0 0 0 0 2 0 0 2 0 0 0 0 0 0 3 3 2 0 2 0 0 2
Barnyardgrass 6 10 0 5 10 8 8 10 10 10 10 10 10 10 10 10 10 8 10 8 9 10
Blackgrass 5 9 0 3 9 4 8 10 10 5 10 8 5 3 10 10 9 7 10 4 10 10
Chickweed 8 10 5 3 7 0 10 8 10 0 7 8 6 5 10 3 6 5 8 3 10 4
Cocklebur 4 3 0 0 0 0 4 0 0 0 0 9 0 - 0 - 0 0 0 0 2 0
Corn 2 5 0 2 3 1 4 7 2 5 2 1 2 3 7 2 2 0 6 1 1 3
Cotton 2 0 0 0 0 0 0 1 0 0 0 0 0 2 2 0 0 0 0 0 1 1
Crabgrass 10 10 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10
Downy bro e 1 0 0 0 2 0 0 3 1 0 0 0 0 0 1 2 2 0 0 0 3 3
Giant foxtail 7 10 7 , 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 7 10 10
Green foxtail 5 10 3 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10
Ji sonweed 5 10 3 5 10 0 10 10 10 2 5 5 9 5 10 9 8 6 8 0 5 8
Johnsongrass 2 10 0 3 10 2 7 10 10 10 10 10 10 10 10 9 8 6 10 8 9 8
Lambsquarters 9 10 10 10 10 9 10 10 10 8 10 10 10 10 10 10 10 10 10 10 8 10
Morningglory 5 10 0 0 9 0 3 10 7 5 7 4 7 8 9 9 10 7 8 7 5 0
Nutsedge 0 3 0 0 2 0 2 8 0 0 0 3 0 0 5 6 4 0 - - 2 0
Rape 8 10 4 8 10 3 9 10 10 4 J.0 0 3 10 10 10 10 6 8 0 8 8
Rice 1 0 0 0 2 0 0 7 10 0 1 0 5 1 1 0 0 0 8 0 1 5
Sicklepod 9 9 0 3 2 0 3 8 0 0 0 - - 3 10 0 5 0 0 2 2 2
Soybean 2 5 0 2 3 0 2 4 0 2 3 0 2 0 4 0 3 0 5 0 2 3
Sugar beet 8 10 3 5 10 2 10 10 10 0 9 9 10 - 10 10 10 5 10 6 9 10
Teaweed 8 7 3 0 8 0 5 5 7 0 4 3 4 3 3 9 8 3 7 0 4 8
Velvetleaf 8 10 3 4 10 8 10 10 8 8 10 8 10 10 10 10 10 8 9 7 8 10
Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 1
Wild buckwheat 9 9 5 6 10 0 8 7 10 2 4 3 0 0 9 7 5 4 5 4 10 9
Wild Oat 5 2 0 0 4 0 2 10 3 0 0 0 0 0 3 5 3 2 0 0 5 6
- 3
CO
TEST C
Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica and Indica rice (Oryza sativa ) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) , bulrush (Scirpus mucronatus) , duck salad (Heteranthera limosa ) , and umbrella sedge ( Cyperus difformis ) , and sprouted tubers of arrowhead (Sagittaria sp . ) and/or waterchestnut (Eleocharis spp.) were planted into this soil. Several days 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 maintaine 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 based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.
Table C Rate CQMgtXIND
5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 74 76 82 103
Arrowhead 1000 - 6 - 9 0 6 8 9 6 7 0 500 0 4 6 - 8 8 0 5 7 9 4 6 9 7 7 6 6 4 0 250 0 0 4 - - 7 6 - 0 0 4 6 0 6 9 8 7 5 4 5 0
Barnyardgrass 1000 - 10 - - - 9 - - 10 - - 10 10 10 - - - - - - 10 10 10 10 10 - - 10 500 8 8 10 10 10 8 - - 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 250 5 6 10 9 7 6 10 10 9 9 10 10 10 9 10 10 10 10 10 10 9 9 10 10 10 10 10 10
Bulrush 1000 - 9 - - - 9 - - 9 - - 9 9 9 10 9 9 10 9 - - 7 500 7 9 10 10 10 9 - - 9 9 10 9 9 9 9 9 10 10 9 9 9 9 10 9 10 8 7 250 7 9 9 9 9 9 10 9 9 9 9 8 8 9 9 9 9 10 9 9 9 9 10 9 9 6 5
Duck Salad 1000 - - - - - - - - 10 - 10 - 10 10 10 - - 10
500 - - - - - - - - 10 10 10 _ 2 - 10 - 10 10 10 10 10 10
250 - - - - - - - - 9 7 10 - 0 - 0 - 10 10 10 10 10 10
Rice (Indica) 1000 - 2 - - - 0 - - 4 - - 4 3 4 0 4 5 5 6 - - 3 500 0 1 2 4 3 0 - - 3 4 3 2 0 2 2 5 5 0 3 3 4 3 0 2 2 250 0 0 0 2 0 0 3 0 2 2 4 1 0 3 0 4 4 0 2 4 4 2 0 0 2
Rice (Japonica)lOOO - 0 - - - 3 6 - - 5 4 4 - - 0 5 6 5 8 - - 3 500 0 0 1 5 4 0 4 5 4 3 2 2 2 5 6 8 0 4 6 5 5 2 3 2 250 0 0 0 4 2 0 0 4 4 1 0 3 0 4 5 8 0 3 4 4 4 0 0 1
Umbrella Sedge 1000 - 9 - - - 10 - - 9 - - 10 10 10 - - - - - - 10 10 10 10 10 - - 10
500 9 9 10 10 10 9 - - 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 250 8 9 9 10 10 9 10 10 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10
Waterchestnut - 9 6 9 10 - - _ _ g 7 9 9 - 3 8 6 10 4 4 7 2 9 9 10 4 8 7 9 8 7 3 5 5 8 0 0 5 0 9 10 9 3 7 9 8 7 2 -
Table C Rate COMPOOND
5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 74 76 82 103
Arrowhead 125 0 0 0 - - - 4 0 - - 4 5- 0 0 0 6 4 5 4 8 5 7 3 2 4
64 - 0 0 - - - 3 0 - - 0 5 0 0 0 0 0 3 3 8 0 6 0 0 3
32 _ _ 0 - - _ 0 0 - - 0 - - - 0 0 0 0 0 5 - 0 0
Barnyardgrass 125 0 0 8 9 7 3 10 8 5 8 10 9 8 7 9 10 10 10 10 10 6 9 10 10 10 9 10 6
64 - 0 5 6 4 0 10 7 0 5 10 8 6 6 6 9 10 10 10 10 4 6 9 10 9 9 8 4
32 - - 3 4 0 - 8 4 - 4 7 - - - 4 6 8 8 9 10 - - - - - 8 6 -
Bulrush 125 8 8 9 9 0 9 6 4 9 9 7 8 9 7 8 8 9 9 9 4 10 9 8 5 4 64 5 7 9 9 0 6 5 0 6 9 5 0 0 6 8 5 9 7 9 0 9 8 6 5 3 32 - 0 6 0 - 5 0 - 0 6 - - 0 6 4 9 7 9 0 4 -
Duck Salad 125 0 6 - 10 - - 0 - - - - _ 10 10 10 10 10 10
64 0 0 - 10 - - 0 - - - - - 10 5 10 10 10 10 32 0 - 0 - - - - - - - - 9 0 -
Rice (Indica) 125 0 0 0 0 0 0 2 0 0 2 4 0 0 0 0 0 0 3 2 5 0 0 2 2 0 0 0 0
64 - 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 4 o o o o o o o o 32 - - 0 0 0 - O 0 - O 0 - - - O 0 O O 2 3 - - - - - 0 0 -
Rice (Japonica) 125 0 0 0 0 0 0 2 0 0 3 4 0 0 0 0 3 0 3 4 6 0 2 4 2 0 0 0 0
64 - 0 0 0 0 0 2 0 0 3 3 0 0 0 0 0 0 0 2 5 0 0 2 0 0 0 0 0
32 - - 0 0 0 - 0 0 - 2 0 - - - 0 0 0 0 0 2 _ - _ _ _ 0 0 -
Umbrella Sedge 125 8 9 10 10 0 10 10 9 9 10 10 9 10 9 10 10 10 10 10 10 10 10 10 9 9 9 9
64 7 9 9 10 0 10 9 8 9 10 9 9 10 8 10 10 10 10 10 9 10 9 9 9 9 8 9 32 - 6 6 5 - 10 7 - 8 10 - - - 5 10 9 10 9 10 - - - - - 9 5 -
Waterchestnut 125 0 8 0 5 4 0 4 0 0 5 0 0 0 0 0 0 0 9 8 9 0 0 9 4 0 -
64 - 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 10 4 9 0 0 0 0 0 - 32 - - 0 0 0 - 0 0 - 0 0 - - - 0 0 0 10 4 9 0 -0 -
Table C Rate COMPODND
5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53 55 56 60 69 71 74 76 82 103 Arrowhead 16 _ _ _ -- _ _ 0 0 - - - - - - - - - - - - - - - - - - - -
Barnyardgrass 16 _ _ - _ _ _ 6 0 Bulrush 16 _ _ _ _ _ - 0 0
Duck Salad 16 - - _ _ _ _ _ _
Rice (Indica) 16 - - _ _ _ _ 0 0
Rice (Japonica) 16 _ _ _ _ _ _ 0 0
Umbrella Sedge 16 _ _ _ _ _ _ g 6
Waterchestnut 16 - _ _ _ _ _ 0 0
I
TEST D
Seeds of spring and winter barley (Hordeum υulgare) , black nightshade (Solanum nigrum ) , blackgrass (Alopecurus myosuroides) , bluegrass (Poa annua) , catchweed bedstraw (Galium aparine) , cheatgrass (Bromus secalinus) , downy brome (Bromus tectorum ) , field pennycress (Thlaspi arvense) , field violet (Viola arvensis) , green foxtail (Setaria viridis) , Italian ryegrass (Lolium multiflorum ) , ivyleaf speedwell (Veronica hederaefolia) , jointed goatgrass (Aegilops cylindrica) , kochia (Kochia scoparia) , lambsquarters ( Chenopodium album ) , Persian speedwell (Veronica persica) , rape (Brassica napus) , Russian thistle (Salsola kali) , scentless chamomile (Matricaria inodora ) , sugar beet (Beta vulgaris) , spring and winter wheat (Triticum aestivum ) , wild buckwheat (Polygonum convolvulus) , and wild oat (Avena fatua ) were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. Postemergence applications of test chemicals were also applied to these same crop and weed species. Plants ranged in height from two to twenty-four cm (two to three leaf stage) for postemergence treatments. Blackgrass and wild oat were treated postemergence at two growth stages — the first stage being at two to three leaves and the second stage being approximately at four leaves or in the initial stages of tillering. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Rates of application of each compound are listed in
Table D. Plant response ratings, summarized in Table D, 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 D COMPOUND
4 9 13 20 23 25 28 32 33 36 37 40 44 46 50 82
(lOOOg/ha) POSTEMERGENCE
TABLE D COMPOOND
13 15 20 23 25 28 32 36 37 40 44 46 49 50 53 55 82
(750g/ha) POSTEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass
Blackgrass (Stage 2) Bluegrass 8 10 10 10 10 9
Catchweed bedstraw 0 0 Cheatgrass 2 • 7 Downy brome 0 8 0 Field pennycress 10 10 10 10 8 10 10 10 10 10 10 10 10 10 10 10 Field violet 10 8 10 10 10 10 10 10 10 10 10 10 10 Green foxtail 10 6 10 9 10 10 9 10 10 10 10 10 10 Italian ryegrass 2 1 8 2 8 3 2 9 9 8 2 Ivyleaf speedwell 10 10 7 10 10 10 10 10 10 10 8 10 10 Jointed goatgrass Kochia 10 8 10 8 10 10 10 10 10 8 10 - 10
Lambsquarters 10 10 10 10 10 10 10 8 10 Persian speedwell 10 10 10 10 8 10 4 10 9 8 Rape 10 9 10 10 10 8 10 10 10 8 Russian thistle 8 8 9 9 9 8
Scentless chamomile 0 2 2 8 0
Sugar beet 8 10 10 10 10 10 10 10 10 10 10 10 10 10
Wheat (Spring)
Wheat (Winter) 0 0
Wild buckwheat 10 10
Wild oat 0 0 8 8
Wild oat (Stage 2) o. 0 8 8
TABLE D COMPOUND
13 15 20 23 25 28 32 33 36 37 40 44 46 48 49
(500g/ha) POSTEMERGENCE
Barley (Spring)
Barley (Winter)
Black nightshade
Blackgrass
Blackgrass (Stage 2)
Bluegrass
Catchweed bedstraw
Cheatgrass
Downy bro e
Field pennycress
Field violet
Green foxtail
Italian ryegrass
Ivyleaf speedwell
Jointed goatgrass
Kochia
Lambsquarters C
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat (Stage 2)
ABLE D COMPOOND
TABLE D COMPOOND
13 15 20 23 25 28 32 33 36 37 40 44 45 46 48 49
(250g/ha) -POSTEMERGENCE
Barley (Spring)
Barley (Winter)
Black nightshade
Blackgrass
Blackgrass (Stage 2)
Bluegrass
Catchweed bedstraw
Cheatgrass
Downy brome
Field pennycress
Field violet
Green foxtail
Italian ryegrass
Ivyleaf speedwell
Jointed goatgrass
Kochia
Lambsquarters
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat (Stage 2)
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100
(250g/ha) POSTEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass
Blackgrass (Stage 2) Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters t Persian speedwell Rape
Russian thistle Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat 10
Wild oat
Wild oat (Stage 2)
TABLE D COMPOUND
13 15 20 23 25 28. 32 33 36 37 40 44 45 46 48 49
(125g/ha) POSTEMERGENCE
Barley (Spring)
Barley (Winter)
Black nightshade
Blackgrass
Blackgrass (Stage 2)
Bluegrass
Catchweed bedstraw
Cheatgrass
Downy bro e
Field pennycress
Field violet
Green foxtail
Italian ryegrass
Ivyleaf speedwell
Jointed goatgrass
Kochia
Lambsquarters C
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat (Stage 2)
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100
Catchweed bedstraw 0 1 1 1 7 3 5 1 4 0 6 8
Cheatgrass 2 3 1 1 2 1 0 0 1 0 1 0
Downy brome 0 2 0 1 2 1 0 0 0 0 1 1
Field pennycress 6 9 8 0 5 3 2 8 5 4 10 3
Field violet 4 9 2 5 7 6 2 7 9 7 6 4
Green foxtail 9 9 , 10 1 8 8 5 2 2 2 10 8
Italian ryegrass 1 7 1 1 4 1 1 1 1 0 3 2
Ivyleaf speedwell 7 7 8 5 7 10 7 9 9 5 10 10
Jointed goatgrass 0 1 1 0 0 1 0 0 1 0 1 0
Kochia 1 2 - 2 6 5 6 8 7 10 8 6 -
•£.
Lambsquarters 0 7 3 1 6 2 0 3 7 5 7 6 ^
Persian speedwell 7 8 6 7 8 8 7 7 9 3 10 8
Rape 6 8 7 3 7 2 4 3 7 3 7 7
Russian thistle - 6 5 0 4 2 0 2 7 4 3 4
Scentless chamomile 0 5 - 0 0 0 0 2 0 0 0 0
Sugar beet 7 9 9 3 9 8 7 9 9 9 10 9
Wheat (Spring) • 0 4 2 0 1 1 1 1 1 0 1 2
Wheat (Winter) 0 2 2 1 1 1 1 1 1 0 1 1
Wild buckwheat 4 1 1 1 0 2 1 2 0 0 6 2
Wild oat 1 2 2 2 2 3 2 1 2 0 3 2
Wild oat (Stage 2) 1 3 2 1 2 1 2 1 2 0 2 1
TABLE D COMPOOND
9 13 15 20 23 32 33 36 37 40 44 45 46 48 49
(64g/ha) POSTEMERGENCE
Barley (Spring)
Barley (Winter)
Black nightshade
Blackgrass
Blackgrass (Stage 2)
Bluegrass
Catchweed bedstraw
Cheatgrass
Downy brome
Field pennycress
Field violet
Green foxtail
Italian ryegrass
Ivyleaf speedwell
Jointed goatgrass
Kochia
Lambsquarters c
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat (Stage 2)
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100 (64g/ha) POSTEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Blackgrass (Stage 2) Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass
KOChia ,&.
Lambsquarters - ~~~
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat ( Stage 2 )
TABLE D COMPOOND
13 23 46 48 56 57 71 73 ' 74 76 82 100
(32g/ha)
POSTEMERGENCE
Barley (Spring)
Barley (Winter)
Black nightshade
Blackgrass
Blackgrass (Stage 2)
Bluegrass
Catchweed bedstraw
Cheatgrass
Downy brome
Field pennycress
Field violet
Green foxtail
Italian ryegrass
Ivyleaf speedwell
Jointed goatgrass
Kochia
Lambsquarters
Persian speedwell
Rape
Russian thistle
Scentless chamomile
Sugar beet
Wheat (Spring)
Wheat (Winter)
Wild buckwheat
Wild oat
Wild oat (Stage 2)
TABLE D COMPOOND
13 20 23 25 28 32 33 36 37 40 44 46 50 82
(lOOOg/ha) , PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass 10 10 10 10 2 Downy brome 10 10 4 Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell 8 10 10 10 10 10 10 10 10 10 8 10 10 10 10 Jointed goatgrass 0 0 Kochia 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 -
Lambsquarters c Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Wheat (Spring) Wheat (Winter) Wild buckwheat 10 10 10 10 10 10 10 10 8 10 10 10 Wild oat 10 10 10 10 10
TABLE D COMPOOND
13 15 20 23 25 28 32 36 37 40 44 46 49 50 53 55 82
(750g/ha) PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet Wheat (Spring) Wheat (Winter) 3 1 0 1 4 1 0 2 2 2 5 9 4 Wild buckwheat 10 10 10 10 10 10 10 10 8 10 10 8 10 10 10 Wild oat 0 0 10 10 4 10 10
TABLE D COMPOOND
13 15 20 23 25 28 32 33 36 37 40 44 46 48 49
(500g/ha) PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw 10 4 10 7 10 1 Cheatgrass Downy brome 0 0 8 Field pennycress 10 1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Field violet 10 9 10 10 10 10 9 10 10 10 10 10 10 10 10 Green foxtail 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass 8 10 2 10 8 8 Ivyleaf speedwell 10 2 10 10 10 10 10 10 9 10 10 8 10 10 10 7 Jointed goatgrass 0 Kochia 9 1 10 10 10 10 9 10 10 10 10 10 10 10 10 10
Lambsquarters 10 8 10 10 10 10 9 10 10 10 9 10 10 10 10 Persian speedwell 10 7 10 10 10 10 10 10 10 10 10 10 10 10 10 10 7 Rape 10 6 8 10 10 10 10 10 10 10 10 10 10 10 10
Russian thistle 10 10 10 8 8 9
Scentless chamomile 8 8 10 7 10
Sugar beet 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10
Wheat (Spring) 0 1 0 2 1 0 1 2 2 2
Wheat (Winter) 1 0 0 1 0
Wild buckwheat 10 10 1 10 10 10 10 10 9 10 10
Wild oat 2 4 2 8 4 6 3 10 9 8 8
TABLE D COMPOOND
50 53 55 56 57 71 73 76 82 84 100
(500g/ha) PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass Downy bro e Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat 10
TABI fs E_D COMPOOND
13 15 20 23 25 28 32 33 36 37 40 44 45 46 48 49
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100
(250g/ha) PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat
COMPOOND
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100
(125g/ha) PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat
TABLE D COMPOOND
4 5 9 13 15 20 23 32 33 36 37 40 44 45 46 48 49 (64g/ha) PREEMERGENCE
Barley (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw
Cheatgrass 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 0
Downy bro e 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0
Field pennycress 0 7 10 6 10 7 10 9 8 10 10 10 10 10 7 8 10
Field violet 0 2 2 3 10 3 10 7 7 8 9 7 8 3 10 8 3
Green foxtail 0 0 1 10 10 8 10 8 10 10 10 10 10 2 8 10 2
Italian ryegrass 0 0 0 0 1 0 2 0 0 5 4 1 1 0 1 1 0
Ivyleaf speedwell 0 0 0 0 2 1 9 8 6 10 7 7 4 0 1 7 0
Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Kochia 0 0 0 7 7 7 1 7 9 , 8 10 5 10 0 4 4 6
Lambsquarters 0 3 2 6 8 3 9 9 7 2 2 1 8 6 2 5 8
Persian speedwell 0 2 0 10 8 3 10 9 2 8 7 7 2 7 10 7 0
Rape 0 8 0 1 7 0 6 7 5 9 8 3 1 0 1 3 0
Russian thistle 0 0 0 2 1 0 2 4 1 2 1 1 1 0 0 0 0
Scentless chamomile 0 0 0 0 0 4 0 3 0 2 1 1 2 0 3 3 0
Sugar beet 0 10 2 6 10 8 10 9 8 9 4 8 7 1 8 8 7
Wheat (Spring) 0 0 * 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wheat (Winter) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Wild buckwheat 0 0 0 0 7 0 5 2 3 2 6 0 0 0 1 0 0
Wild oat 0 0 0 0 1 0 1 0 0 5 2 1 1 0 0 1 0
TABLE D COMPOOND
50 53 55 56 57 71 73 74 76 82 84 100
(64g/ha)
PREEMERGENCE
Barley (Spring) Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw Cheatgrass Downy brome Field pennycress Field violet Green foxtail Italian ryegrass Ivyleaf speedwell Jointed goatgrass Kochia
Lambsquarters Persian speedwell Rape
Russian thistle Scentless chamomile Sugar beet Wheat (Spring) Wheat (Winter) Wild buckwheat Wild oat
TABLE D COMPOOND
5 13 23 46 48 56 57 71 73 74 76 82 100 (32g/ha) PREEMERGENCE
Barley (Spring) 0 0 0 0 0 0 0 0 0 0 0 0 0
Barley (Winter) Black nightshade Blackgrass Bluegrass
Catchweed bedstraw
Cheatgrass 0 0 0 0 0 0 1 0 1 0 0 Q
Downy brome 0 0 0 0 0 0 0 0 0 0 0 0
Field pennycress 3 6 7 2 2 5 7 4 10 10 8 5
Field violet 1 0 9 0 8 7 8 8 7 4 8 3
Green foxtail 0 5 2 8 8 2 9 7 7 7 5 2
Italian ryegrass 0 0 0 0 0 0 2 0 1 1 0 0
Ivyleaf speedwell 0 0 7 0 3 0 3 2 4 8 3 0
Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0
Kochia 0 6 0 0 0 0 2 0 1 5 1 0
Lambsquarters 0 0 7 0 2 6 6 2 9 9 4 0 c
Persian speedwell 0 0 8 3 2 7 8 7 8 10 6 0 c
Rape 3 0 2 0 0 1 2 0 1 2 5 0
Russian thistle 0 0 0 0 0 0 0 0 0 2 1 0
Scentless chamomile 0 0 0 1 0 1 2 2 2 7 1 2
Sugar beet 6 6 10 6 3 6 8 6 7 10 7 3
Wheat (Spring) 0 0 0 0 0 0 0 0 0 0 0 0
Wheat (Winter) 0 0 0 0 0 0 0 0 1 0 0 0
Wild buckwheat 0 0 2 0 0 0 1 0 0 3 2 0
Wild oat 0 0 0 0 0 0 2 2 1 0 0 0
TEST E
Seeds selected from barnyardgrass (Echinochloa crus-galli), bermudagrass (Cynodon dactylon) , cocklebur (Xanthium pensylvanicum) , cotton (Gossypium hirsutum) , fall panicum (Panicum dichotomiβorum) , goosegrass (Eleusine indica) , ground cherry (Physalis heterophylla) , johnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , large crabgrass (Digitaria sanguinalis), morningglory (Ipomoea hederacea) , purslane (Portulaca oleracea) , redroot pigweed (Amaranthus retroβexus) , sicklepod (Cassia obtusifolia) , signalgrass (Brachiaria platyphylla ) , s a r tweed (Polygonum persicaria ) , teaweed (Sida spinosa) , and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
RATE (g/ha) PREEMERGENCE Barnyardgrass Bermudagrass Cocklebur Cotton
Fall Panicum Goosegrass Ground cherry Johnsongrass Lambsquarters Large crabgrass Morningglory Nutsedge Purslane Redroot pigweed 100 100 100 100 70 Sicklepod Signalgrass Smartweed Teaweed Velvetleaf
Table E
Cmpd 53
TEST F
Seeds of barnyardgrass (Echinochloa crus-galli) , black nightshade (Solanum nigrum) , cocklebur (Xanthium pensylvanicum) , corn (Zea mays) , f all panicum (Panicum dichotomiβorum) , giant foxtai l (Setaria faberi) , green foxtai l (Setaria viridis) , hemp sesbania (Sesbania exaltata) , j imson eed (Datura stramonium) , j ohnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album) , large crabgrass (Digitaria sanguinalis) , morningglory (Ipomoea hederacea) , redroot pigweed (Amaranthus retroflexus) , sicklepod (Cassia obtusifolia) , signalgrass (Brachiaria platyphylla ) , sma r weed (Polygonum persicaria ) , soybean ( Gly cine max) , teaweed (Sida spinosa) , and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tubers were planted in a si lt loam soi l and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent . Treated plants and controls were maintained in a greenhouse for approximately 21 days , after which all species were compared to controls and visually evaluated . Response ratings , summarized in Table F , are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control . A dash (-) response means no test result .
165
Table F
Cmpd 13
RATE (g/ha) 1000 500 250 125 64 PREEMERGENCE
Barnyardgrass 100 70 20 0 0
Black nightshade 100 20 0 0 0
Cocklebur 30 20 0 0 0
Corn 40 15 10 0 0
Fail panicum -
Giant foxtail 100 100 100 100 20
Green foxtail 100 100 100 70 30
Kemp sesbania 100 70 30 0 0
Jimsonweed 100 20 0 0 0
Johnsongrass 45 20 0 0 0
Lambsquarters 100 100 98 98 30
Large crabgrass 100 100 100 70 0 Morningglory 100 70 0 0 0
Nutsedge 75 50 0 0 0
Redroot pigweed 100 100 100 100 95
Sicklepod 30 0 0 0 0
Signalgrass 100 100 100 80 70
Smartweed 30 0 0 0 0
Soybean 90 30 10 0 0
Teaweed 30 0 0 0 0 Velvetleaf 100 80 30 0 0
RATE (g/ha) PREEMERGENCE Barnyardgrass Black nightshade Cocklebur Corn
Fall panicum Giant foxtail Green foxtail Hemp sesbania Jimsonweed Johnsongrass Lambsquarters Large crabgrass Morninglory Nutsedge Redroot pigweed Sicklepod Signalgrass Smartweed Soybean Teaweed Velvetleaf
Cmpd 23
RATE (g/ha) 1000 500 250 125 64 PREEMERGENCE Barnyardgrass Black nightshade Cocklebur Corn Fall panicum -- --- C- j- c-'-r-.i-.α-L ±
Green foxtail
Hemp sesbania
Jimsonweed
Johnsongrass
Lambsquarters
Large crabgrass
Morningglory
Nutsedge
Redroot pigweed
Sicklepod
Signalgrass
Smartweed
Soybean
Teaweed
Velvetleaf
Table F
RATE (g/ha) PREEMERGENCE Barnyardgrass Black nightshade Cocklebur Corn
Fall panicum Giant foxtail Green foxtail Hemp sesbania Jimsonweed Johnsongrass Lambsquarters Large crabgrass Morningglory
Nutsedge
Redroot pigweed
Sicklepod
Signalgrass
Smartweed
Soybean
Teaweed
Velvetleaf
TEST G
Seeds of barnyardgrass (Echinochloa crus-galli ) , cocklebur (Xanthium pensylvanicum ) , corn (Zea mays ) , crabgrass (Digitaria spp.)/ fall panicum (Panicum dichotomiβorum. ) , giant foxtail (Setaria faberi ) , green foxtail (Setaria viridis ) , jimsonweed (Datura stramonium ) , johnsongrass (Sorghum halepense) , lambsquarters (Chenopodium album ) , morningglory (Ipomoea hederacea ) , redroot pigweed (Amaranthus retroβexus) , smartweed (Polygonum persicaria) , sorghum (Sorghum bicolor) , soybean (Gly cine max) , and velvetleaf (Abutilon theophrasti) and purple nutsedge ( Cyperus rotundus ) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. Several of the test compounds were also applied postemergence to these crop and weed species . For postemergence applications, plants were from two to twenty-five cm tall.
The soil surface of an additional container of corn (Corn, Perlite) to be treated postemergence was covered with the absorbent, perlite, before postemergence treatments were applied. After application of test compounds, the perlite was removed from the soil surface to remove chemical sorbed onto the perlite. This procedure would therefore allow only that portion of chemical sorbed onto the plant foliage to cause corn injury response.
Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. Test rates for each compound are listed
in Table G. The ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table G Cmpd 5
RATE (g/ha) 1000 500 250 125 64
POSTEMERGENCE
Barnyardgrass 70 35
20 0 0 Cocklebur 35 2 5
Corn o o o
40 20 0 0 0
Corn (Perlite) 25 0
0 0 0
- lu - C (i--5- 80 50 35 0
0
Fall panicum 45 20 0 0 0 Giant foxtail 35 0 0 0 0 Green foxtail 60 25
0 0 0
Jimsonweed 100 95 85 45 0
Johnsongrass 40 25 0 0 0
Lambsquarters --
Morningglory 65 40 35 20 0 Nutsedge 0 0 0 0 n
Redroot pigweed 100 100 95 75
35
Smartweed 40 25
Sorghum 45 2 0 o o o o o o
Soyb an 85 65 40 20 0
Velvetleaf 55 25 20 0 . 0
PREEMERGENCE
Barnyardgrass 75 45 25 0
Cocklebur 0 0 0 0
Corn 25 0 0 0
Crabgrass 65 40 20 0
Fall panicum 50 35 0 0
Giant foxtail 20 0 0 0
Green foxtail 45 25 0 0 Jimsonweed 100 75 35 0
Johnsongrass 55 40 20 0
Lambsquarters 100 100 65 40
Morningglory 40 0 0 0
Nutsedge .0 0 0 0
Redroot pigweed 100 100 70 40
Smartweed 55 35 2 0 0 Sorghum 20 0 0 0
Soybean 40 0 0 0
Velvetleaf 100 60 25 0
Table G
32 16
Table G Cmpd 23
RATE ( g / ha) 1000 500 250 125 54 - - κ
PREEMERGENCE 15
Barnyardgrass Cocklebur Corn
Crabgrass Fall panicum Giant foxtail Green foxtail Jimsonweed Johnsongrass Lambsquarters Morningglory Nutsedge Redroot pigweed Smartweed Sorghum Soybean Velvetleaf
Table G
Cmpd 32
Cmpd 36
Table G
Cmpd 50
TEST H
Seeds of blackgrass (Alopecurus myosuroides ) , catchweed bedstraw (Galium aparine ) , chickweed (Stellaria media) , knotweed (Polygonum aviculare ) , lambsquarters (Chenopodium album ) , Persian speedwell (Veronica persica) , scentless chamo ile (Matricaria inodora ) , sugar beet (Beta vulgaris) , viola (Viola arvensis ) , wheat (Triticum aestiυum) , wild buckwheat (Polygonum convolvulus ) , and wild oat (Avena fatua ) were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. These crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to twenty cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species " were compared to controls and visually evaluated.
Application rates for each test chemical are shown in Table H. Plant response ratings, summarized in Table H, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control- A dash (-) response means no test result.
125
0
0
0
70
50
70
0
0
0
0
0
0
0 0 0 0 0 0
30 0 0 0
20 0
Table H
Cmpd 36
RATE (g/ha) 2000 1500
POSTEMERGENCE Blackgrass Catchweed bedstraw Chickweed Knotweed Lambsquarters Persian speedwell Scentless chamomille Sugar beet Viola Wheat
Wild buckwheat Wild oat
PREEMERGENCE Blackgrass Catchweed bedstraw Chickweed Knotweed Lambsquarters Persian speedwell Scentless chamomille Sugar beet Viola Wheat
Wild buckwheat Wild oat
Table H
Gmpd 68
TEST I
Seeds of alfalfa (Medicago sativa) , barley
(Hordeum vulgare) , bluegrass (Poa pratensis ) , corn (Zea mays ) , cotton (Gossypium hirsutum) , flax (Linum usitatissimum ) , oat (Avena sativa ) , pea (sativum ) , peanut (Arachis hypogaea) , rape (Brassica napus) , rice (Oryza sativa ) , sorghum (Sorghum bicolor) , soybean (Glycine max) , sugar beet (Beta vulgaris ) , sunflower (Helianthus annuus) , tomato (Lycopersicon esculentum) , and wheat (Triticum aestivum) were planted and treated preemergence with a test chemical dissolved in a non-phytotoxic solvent. These crop species were also treated with postemergence applications of the test chemical. Plants ranged in height from four to twenty cm (two to three leaf stage) when post-emergence applications were applied. " Treated plants and controls were grown under greenhouse conditions for approximately twenty-four days, after which all plants treated with the test chemical were compared to untreated controls and visually evaluated for injury response. Application rates for the test chemical are shown in Table I. Plant response ratings, summarized in Table I, are from 0 to 100 where 0 is no injury and 100 is complete control. A dash (-) response means no test result.
Table I
Cmpd 15
125
25 0 0
20 0
0 20 20 20
0 15 25 35
20 0
35 20 65 30
0 40 25
0
0
100
35
35
25
100
0 70 25