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Details for Patent: 4,797,150

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Details for Patent: 4,797,150

Title: Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
Abstract:Compounds of the formula ##STR1## wherein R.sup.60 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.61 through R.sup.66 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.
Inventor(s): Carter; Charles G. (Silver Spring, MD)
Assignee: Stauffer Chemical Company (Westport, CT)
Filing Date:Nov 30, 1987
Application Number:07/126,449
Claims:1. Compounds of the formula ##STR17## wherein R.sup.60 is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n - wherein n is 0 to 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy;

R.sup.61 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.62 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.61 and R.sup.62 together are R.sub.2 -C.sub.5 alkylene;

R.sup.63 is C.sub.1 -C.sub.4 alkyl;

R.sup.64 is C.sub.1 -C.sub.4 alkyl; or

R.sup.63 and R.sup.64 together are C.sub.2 -C.sub.5 alkylene;

R.sup.65 and R.sup.66 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; and (13) -N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined and their salts.

2. The compounds of claim 1 wherein R.sup.60 is chlorine, hydrogen, bromine, methyl, methoxy, nitro, trifluoromethyl or methylsulfonyl; R.sup.61, R.sup.62, R.sup.63 and R.sup.64 are methyl; R.sup.65 and R.sup.66 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; or (13) -N-(R.sup.c)C(O)R.sup.d are as defined.

3. The compounds of claim 2 wherein R.sup.65 and R.sup.66 are independently are hydrogen; chlorine; fluorine; bromine; methyl; C.sub.1 -C.sub.4 alkoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n - wherein n is the integer 0 or 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl; ethyl or n-propyl, R.sup.e C(O)- where R.sup.e is C.sub.1 -C.sub.4 alkyl; or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.65 is in the 3-position or 5-position and R.sup.66 is in the 4-position.

4. The compounds of claim 2 wherein R.sup.65 is hydrogen and R.sup.66 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.

5. The compound of claim 2 wherein R.sup.60 is nitro, R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is hydrogen.

6. The compound of claim 2 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is 4-chlorine.

7. The compound of claim 2 wherein R.sup.60 is chlorine; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 CH.sub.3.

8. The compound of claim 2 wherein R.sup.60 is methyl; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 C.sub.2 H.sub.5.

9. The compound of claim 2 wherein R.sup.60 is trifluoromethyl; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-trifluoromethyl.

10. The compound of claim 2 wherein R.sup.60 is nitro, R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 CH.sub.3.

11. The compound of claim 2 wherein R.sup.60 is hydrogen; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.6 is 4-trifluoromethylthio.

12. The compound of claim 2 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-cyano.

13. The compound of claim 2 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 -n-C.sub.3 H.sub.7.

14. The compound of claim 2 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is 4-trifluoromethyl.

15. The compound of claim 2 wherein R.sup.60 is chlorine; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is 3-ethoxy; and R.sup.66 is 4-SO.sub.2 CH.sub.2 CH.sub.3.

16. The compounds of claim 2 wherein R.sup.65 is hydrogen.

17. The compounds of claim 3 wherein R.sup.65 is hydrogen.

18. An herbicidal composition comprising an herbicidally active 2-benzoyl-substituted-1,3,5-cyclohexanetrione compound of the formula ##STR18## wherein R.sup.60 is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is nitro; alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoro-C.sub.1 -C.sub.2 methoxy;

R.sup.61 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.62 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.61 and R.sup.62 together are C.sub.2 -C.sub.5 alkylene;

R.sup.63 is C.sub.1 -C.sub.4 alkyl;

R.sup.64 is C.sub.1 -C.sub.4 alkyl; or

R.sup.63 and R.sup.64 together are C.sub.2 -C.sub.5 alkylene;

R.sup.65 and R.sup.66 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; and (13) -N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined and their salts and an inert carrier therefor.

19. The composition of claim 18 wherein R.sup.60 is hydrogen, chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl or methylsulfonyl; R.sup.61, R.sup.62, R.sup.63 and R.sup.64 are methyl; R.sup.65 and R.sup.66 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 m 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; or (13) -N-(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined.

20. The composition of claim 19 wherein R.sup.65 and R.sup.66 are independently are hydrogen; chlorine; fluorine; bromine; methyl; C.sub.1 -C.sub.4 alkoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n - wherein n is the integer 0 or 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; R.sup.e C(O)- where R.sup.e is C.sub.1 -C.sub.4 alkyl; or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.65 is in the 3-position or 5-position and R.sup.66 is in the 4-position.

21. The composition of claim 19 wherein R.sup.65 is hydrogen and R.sup.66 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.

22. The composition of claim 19 wherein R.sup.60 is nitro, R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is hydrogen.

23. The composition of claim 19 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is 4-chlorine.

24. The composition of claim 19 wherein R.sup.60 is chlorine; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 CH.sub.3.

25. The composition of claim 19 wherein R.sup.60 is methyl; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 C.sub.2 H.sub.5.

26. The composition of claim 19 wherein R.sup.60 is trifluoromethyl; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-trifluoromethyl.

27. The composition of claim 19 wherein R.sup.60 is nitro, R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 CH.sub.3.

28. The composition of claim 19 wherein R.sup.60 is hydrogen; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is 4-trifluoromethylthio.

29. The composition of claim 19 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-cyano.

30. The composition of claim 19 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen and R.sup.66 is 4-SO.sub.2 -n-C.sub.3 H.sub.7.

31. The composition of claim 19 wherein R.sup.60 is nitro; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is hydrogen; and R.sup.66 is 4-trifluoromethyl.

32. The composition of claim 19 wherein R.sup.60 is chlorine; R.sup.61 is methyl; R.sup.62 is methyl; R.sup.63 is methyl; R.sup.64 is methyl; R.sup.65 is 3-ethoxy; and R.sup.66 is 4-SO.sub.2 CH.sub.2 CH.sub.3.

33. The compositions of claim 19 wherein R.sup.65 is hydrogen.

34. The compositions of claim 20 wherein R.sup.65 is hydrogen.

35. Compounds of the formula ##STR19## wherein R.sup.60 is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy;

R.sup.61 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.62 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.61 and R.sup.62 together are C.sub.2 -C.sub.5 alkylene;

R.sup.63 is C.sub.1 -C.sub.4 alkyl;

R.sup.64 is C.sub.1 -C.sub.4 alkyl; or

R.sup.63 and R.sup.64 together are C.sub.2 -C.sub.5 alkylene;

R.sup.65 and R.sup.66 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; and (13) -N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined.
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