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Details for Patent: 4,816,066

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Details for Patent: 4,816,066

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 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): Michaely; William J. (El Cerrito, CA), Kraatz; Gary W. (San Jose, CA)
Assignee: Stauffer Chemical Company (Westport, CT)
Filing Date:Dec 04, 1987
Application Number:07/129,026
Claims:1. A compound having the structural formula ##STR95## wherein R.sup.10 is C.sub.1 -C.sub.6 alkyl;

R.sup.11 is hydrogen, C.sub.1 -C.sub.6 alkyl, or ##STR96## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl or R.sup.10 and R.sup.11 together are alkylene having 3 to 6 carbon atoms;

R.sup.12 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy;

R.sup.13 and R.sup.14 independently are: (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 aliphatic alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; ##STR97## wherein R.sup.c is C.sub.1 -C.sub.4 alkyl and R.sup.j is hydrogen; (11) R.sup.f C(O) wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; (12) --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (13) R.sup.13 and R.sup.14 together can form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached; or (14) R.sup.13 and R.sup.14 are the groups phenoxy or substituted phenoxy wherein the substituent is halogen or halomethyl or both;

R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.16 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.15 and R.sup.16 together may form a substituted or unsubstituted alkylene ring of 2-5 carbon atoms, the substituent being one or two methyl groups; and their salts.

2. The compound of claim 1 wherein R.sup.10 is C.sub.1 -C.sub.4 alkyl; R.sup.11 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR98## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; or R.sup.10 and R.sup.11 together are alkylene having 3 to 6 carbon atoms; R.sup.12 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; R.sup.13 and R.sup.14 independently are: (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 aliphatic alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; or (9) R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.16 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; and their salts.

3. The compound of claim 1 wherein R.sup.10 is is C.sub.1 -C.sub.4 alkyl; R.sup.11 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.12 is chlorine, bromine, iodine or methoxy; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.16 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; and their salts.

4. The compound of claim 2 wherein R.sup.10 is methyl; R.sup.11 is hydrogen or methyl; R.sup.12 is chlorine, bromine, iodine or methoxy; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen or methyl; R.sup.17 is hydrogen or methyl; and R.sup.18 is hydrogen or methyl; and their salts.

5. The compound of claim 3 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4-chlorine, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

6. The triethanolammonium salt of the compound of claim 5.

7. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--CH.sub.3 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen and its salts.

8. The compound of claim 2 wherein R.sup.10 is methyl; R.sup.11 is hydrogen or methyl; R.sup.12 is chlorine or bromine; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen or methyl; R.sup.17 is hydrogen or methyl; and R.sup.18 is hydrogen or methyl; and their salts.

9. The compound of claim 2 wherein R.sup.10 is methyl; R.sup.11 is methyl; R.sup.12 is chlorine; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen; R.sup.17 is hydrogen or methyl; and R.sup.18 is hydrogen.

10. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--C.sub.2 H.sub.5 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen and its salts.

11. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methoxy, R.sup.14 is 4--CH.sub.3 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen and its salts.

12. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methoxy, R.sup.14 is 4-bromine, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

13. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-ethoxy, R.sup.14 is 4-bromine, R.sup.15 is methyl, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

14. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--n--CH.sub.3 H.sub.7 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

15. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methylthio, R.sup.14 is 4--C.sub.2 H.sub.4 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

16. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--C.sub.2 H.sub.5 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

17. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--C.sub.2 H.sub.4 SO--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

18. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--CH.sub.3 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen, R.sup.18 is hydrogen, and its salts.

19. The compound of claim 2 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--CH.sub.3 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

20. 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 ##STR99## wherein R.sup.10 is C.sub.1 -C.sub.4 alkyl;

R.sup.11 is hydrogen, C.sub.1 -C.sub.4 alkyl, or ##STR100## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl or R.sup.10 and R.sup.11 together are alkylene having 3 to 6 carbon atoms;

R.sup.12 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy;

R.sup.13 and R.sup.14 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 aliphatic alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2, ##STR101## wherein R.sup.c is C.sub.1 -C.sub.4 alkyl and R.sup.j is hydrogen; (11) R.sup.f C(0) wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; (12) --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (13) R.sup.13 and R.sup.14 together can form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached; or (14) R.sup.13 and R.sup.14 are the groups phenoxy or substituted phenoxy wherein the substituent is halogen or halomethyl or both;

R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.16 is hydrogen or C.sub.1 -C.sub.1 -C.sub.4 alkyl;

R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.15 and R.sup.16 together may form a substituted or unsubstituted alkylene ring of 2-5 carbon atoms, the substituent being oe or two methyl groups; and their salts.

21. The method of claim 20 wherein R.sup.10 is C.sub.1 -C.sub.4 alkyl; R.sup.11 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR102## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; or; R.sup.10 and R.sup.11 are alkylene having 3 to 6 carbon atoms; R.sup.12 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; R.sup.13 and R.sup.14 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 aliphatic alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; or (9) R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; and R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.16 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; and their salts.

22. The method of claim 21 wherein R.sup.10 is C.sub.1 -C.sub.4 alkyl; R.sup.11 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.12 is chlorine, bromine, iodine or methoxy; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alky; and n is the integer 0 or 2; R.sup.15 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.16 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.17 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.18 is hydrogen or C.sub.1 -C.sub.4 alkyl; and their salts.

23. The method of claim 21 wherein R.sup.10 is methyl; R.sup.11 is hydrogen or methyl; R.sup.12 is chlorine, bromine, iodine or methoxy; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen or methyl; R.sup.17 is hydrogen or methyl; and R.sup.18 is hydrogen or methyl; and their salts.

24. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4-chlorine, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

25. The method of claim 24 wherein the salt is the triethanolammonium salt.

26. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--CH.sub.3 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen and its salts.

27. The method of claim 20 wherein R.sup.10 is methyl; R.sup.11 is hydrogen or methyl; R.sup.12 is chlorine or bromine; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen or methyl; R.sup.17 is hydrogen or methyl; R.sup.18 is hydrogen or methyl; and their salts.

28. The method of claim 20 wherein R.sup.10 is methyl; R.sup.11 is methyl; R.sup.12 is chlorine; R.sup.13 and R.sup.14 independently are hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl; and n is the integer 0 or 2; R.sup.15 is hydrogen or methyl; R.sup.16 is hydrogen; R.sup.17 is hydrogen or methyl; and R.sup.18 is hydrogen; and their salts.

29. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--C.sub.2 H.sub.5 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

30. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methoxy, R.sup.14 is 4-CH.sub.3 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen, R.sup.18 is hydrogen, and its salts.

31. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methoxy, R.sup.14 is 4-bromine, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

32. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-ethoxy, R.sup.14 is 4-bromine, R.sup.15 is methyl, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

33. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--n--C.sub.3 H.sub.7 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

34. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-methylthio, R.sup.14 is 4--C.sub.2 H.sub.5 SO.sub.2 --, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

35. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--C.sub.2 H.sub.5 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

36. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--C.sub.2 H.sub.5 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

37. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is hydrogen, R.sup.14 is 4--CH.sub.3 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen, R.sup.18 is hydrogen, and its salts.

38. The method of claim 21 wherein R.sup.10 is methyl, R.sup.11 is methyl, R.sup.12 is chlorine, R.sup.13 is 3-chlorine, R.sup.14 is 4--CH.sub.3 S--, R.sup.15 is hydrogen, R.sup.16 is hydrogen, R.sup.17 is hydrogen and R.sup.18 is hydrogen, and its salts.

39. An herbicidal composition comprising an herbicidally active 2-(2'halogen or alkoxy substituted benzoyl)-4-alkyl-1,3-cyclohexanedione and an inert carrier therefor.

40. The herbicidal composition of claim 39 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy.

41. The herbicidal composition of claim 39 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or methoxy.

42. The herbicidal composition of claim 39 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy and the 4-position of the 1,3-cyclohexanedione moiety substituted with one or two C.sub.1 -C.sub.4 alkyl groups.

43. The herbicidal composition of claim 39 wherein the 2-position of the benzoyl moiety is substituted with chlorine or bromine and the 4-position of the 1,3-cyclohexanedione moiety is substituted with one or two methyl groups.
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