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Details for Patent: 4,853,028

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Details for Patent: 4,853,028

Title: Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
Abstract:Compounds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro, (S(O).sub.n R wherein R is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.2 through R.sup.8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.
Inventor(s): Carter; Charles G. (San Francisco, CA), Lee; David L. (Martinez, CA), Michaely; William J. (Richmond, CA)
Assignee: Stauffer Chemical Company (Westport, CT)
Filing Date:Dec 04, 1987
Application Number:07/128,126
Claims:1. Compounds of the formula ##STR96## wherein n is the integer 0, 1 or 2;

R.sup.40 is C.sub.1 -C.sub.4 alkyl;

R.sup.41 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.42 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR97## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; or R.sup.41 and R.sup.42 together are alkylene having 3 to 6 carbon atoms;

R.sup.43 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.44 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.45 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.46 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.47 and R.sup.48 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n 13 wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.r R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined, with the proviso that R.sup.47 is not attached to the 6-position and their salts.

2. The compound of claim 1 wherein n is 2; R.sup.40 is methyl; R.sup.41 is hydrogen or methyl; R.sup.42 is hydrogen or methyl; R.sup.43 is hydrogen or methyl; R.sup.44 is hydrogen or methyl; R.sup.45 is hydrogen or methyl; R.sup.46 is hydrogen or methyl; R.sup.47 and R.sup.48 indepently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined.

3. The compound of claim 2 wherein R.sup.47 and R.sup.48 are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n --wherein n is the integer 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.e C(O)--where R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.47 is in the 3-position.

4. The compound of claim 2 wherein R.sup.47 is hydrogen and R.sup.48 is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl.

5. The compound of claim 1 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is hydrogen.

6. The compound of claim 1 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is methyl; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is hydrogen.

7. The compound of claim 1 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is chlorine.

8. The compound of claim 1 wherein n is two; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is chlorine.

9. The compound of claim 1 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

10. The compound of claim 1 wherein n is two; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

11. The compound of claim 1 wherein n is zero; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

12. The compound of claim 1 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

13. The compound of claim 1 wherein n is one; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

14. The compound of claim 1 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is methylthio.

15. The compound of claim 1 wherein n is one; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is CH.sub.3 S(O)--.

16. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula ##STR98## wherein n is the integer 0, 1 or 2;

R.sup.40 is C.sub.1 -C.sub.4 alkyl;

R.sup.41 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.42 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR99## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; or R.sup.41 and R.sup.42 together are alkylene having 3 to 6 carbon atoms;

R.sup.43 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.44 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.45 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.46 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.47 and R.sup.48 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--whrein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined, with the proviso that R.sup.47 is not attached to the 6-position or its salts.

17. The method of claim 16 wherein n is 2; R.sup.40 is is methyl; R.sup.41 is hydrogen or methyl; R.sup.42 is methyl; R.sup.43 is hydrogen or methyl; R.sup.44 is hydrogen or methyl; R.sup.45 is hydrogen or methyl; R.sup.46 is hydrogen or methyl; R.sup.47 and R.sup.48 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined.

18. The method of claim 17 wherein R.sup.47 and R.sup.48 are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n --wherein n is the integer 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.e C(O)--where R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.47 is in the 3-position.

19. The method of claim 16 wherein R.sup.47 is hydrogen and R.sup.48 is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl.

20. The method of claim 16 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is hydrogen.

21. The method of claim 16 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is methyl; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is hydrogen.

22. The method of claim 16 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is chlorine.

23. The method of claim 16 wherein n is two; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is chlorine.

24. The method of claim 16 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

25. The method of claim 16 wherein n is two; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

26. The method of claim 16 wherein n is zero; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

27. The method of claim 16 wherein n is two; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

28. The method of claim 16 wherein n is one; R.sup.40 is methyl; R.sup.41 is methyl; R.sup.42 is methyl; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is hydrogen; and R.sup.48 is trifluoromethyl.

29. The method of claim 16 wherein n is zero; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is methylthio.

30. The method of claim 16 wherein n is one; R.sup.40 is methyl; R.sup.41 is hydrogen; R.sup.42 is hydrogen; R.sup.43 is hydrogen; R.sup.44 is hydrogen; R.sup.45 is hydrogen; R.sup.46 is hydrogen; R.sup.47 is 3-chlorine; and R.sup.48 is CH.sub.3 S(O)--.

31. An heribicidal composition comprising an herbicidally active 2-(2-C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl benzoyl)1,3-cyclhexanedione or its salts and an inert carrier therefor.

32. The herbicidal composition of claim 31 wherein the 2-(2-C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl benzoyl-1,3-cyclohexanedione is a compound of the formula ##STR100## wherein n is the integer 0, 1 or 2;

R.sup.40 is C.sub.1 -C.sub.4 alkyl;

R.sup.41 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.42 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR101## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; or R.sup.41 and R.sup.42 together are alkylene having 3 to 6 carbon atoms;

R.sup.43 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.44 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.45 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.46 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.47 and R.sup.48 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined, with the proviso that R.sup.47 is not attached to the 6-position.

33. The herbicidal composition of claim 32 wherein n is 2; R.sup.40 is methyl; R.sup.41 is hydrogen or methyl; R.sup.42 is hydrogen or methyl; R.sup.43 is hydrogen or methyl; R.sup.44 is hydrogen or methyl; R.sup.45 is hydrogen or methyl; R.sup.46 is hydrogen or methyl; R.sup.47 and R.sup.48 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (=b 5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 to 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined.

34. The herbicidal composition of claim 33 wherein R.sup.47 and R.sup.48 are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n --wherein n is the integer 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.e C(O)--where R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.47 is in the 3-position.
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