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Claims for Patent: 5,006,158

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Summary for Patent: 5,006,158
Title: Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
Abstract:Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.7 is hydrogen or 3-C.sub.1 -C.sub.4 alkoxy; and R.sup.8 is (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) OCF.sub.3 ; (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, their use as herbicides and herbicidal compositions containing the compounds.
Inventor(s): Carter; Charles G. (San Francisco, CA), Lee; David L. (Martinez, CA), Michaely; William J. (Richmond, CA), Kraatz; Gary W. (San Jose, CA)
Assignee: ICI Americas Inc. (Wilmington, DE)
Application Number:07/128,128
Patent Claims: 1. Compounds of the formula ##STR97## wherein R.sup.31 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.32 is hydrogen or C.sub.1 -C.sub.4 alkyl ; or

R.sup.31 and R.sup.32 together are alkylene having 3 to 6 carbon atoms;

R.sup.33 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.34 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.35 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.36 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.37 is hydrogen or 3-C.sub.1 -C.sub.4 alkoxy; and

R.sup.38 is (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 their herbicidally effective salts.

2. The compounds of claim 1 wherein R.sup.31 is hydrogen or methyl; R.sup.32 is hydrogen or methyl; R.sup.33 is hydrogen or methyl; R.sup.34 is hydrogen or methyl; R.sup.35 is hydrogen or methyl; R.sup.36 is hydrogen or methyl; R.sup.37 is hydrogen or 3-C.sub.1 -C.sub.4 alkoxy; and R.sup.38 is (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 compounds of claim 2 wherein R.sup.37 is hydrogen or 3-methoxy and R.sup.38 is 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.37 is in the 3-position.

4. The compounds of claim 2 wherein R.sup.37 is hydrogen and R.sup.38 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 or C.sub.1 -C.sub.4 haloalkyl.

5. The compound of claim 2 wherein R.sup.31 is methyl; R.sup.32 is methyl, R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is hydrogen.

6. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is methylthio.

7. The compound of claim 2 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluoromethyl.

8. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluoromethyl.

9. The compound of claim 2 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is ClCH.sub.2 SO.sub.2 --.

10. The compound of claim 2 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is fluorine.

11. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is chlorine.

12. The compound of claim 2 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2 --.

13. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is n-C.sub.3 H.sub.7 SO.sub.2.

14. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2.

15. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is C.sub.2 H.sub.5 SO.sub.2.

16. The compounds of claim 2 wherein R.sup.37 is hydrogen.

17. The compounds of claim 4 wherein R.sup.31 and R.sup.32 are both hydrogen or both methyl and R.sup.33, R.sup.34, R.sup.35 and R.sup.36 are hydrogen.

18. The compounds of claim 4 wherein R.sup.38 is --SO.sub.2 CH.sub.3.

19. The compounds of claim 4 wherein R.sup.38 is --SO.sub.2 CH.sub.2 Cl.

20. The compounds of claim 4 wherein R.sup.38 is trifluoromethyl.

21. The compounds of claim 4 wherein R.sup.38 is --SO.sub.2 CH.sub.3.

22. The compounds of claim 4 wherein R.sup.38 is chlorine.

23. The compounds of claim 4 wherein R.sup.38 is --SO.sub.2 CH.sub.2 Cl.

24. The compounds of claim 4 wherein R.sup.38 is --SO.sub.2 --n--C.sub.3 H.sub.7.

25. The compound of claim 2 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen, R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is cyano.

26. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the structural formula ##STR98## wherein R.sup.31 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.32 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.31 and R.sup.32 together are alkylene having 3 to 6 carbon atoms;

R.sup.33 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.34 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.35 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.36 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.37 is hydrogen or 3-C.sub.1 -C.sub.4 alkoxy; and

R.sup.38 is (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 its herbicidally effective salts.

27. The method of claim 26 wherein R.sup.31 is hydrogen or methyl; R.sup.32 is hydrogen or methyl; R.sup.33 is hydrogen or methyl; R.sup.34 is hydrogen or methyl; R.sup.35 is hydrogen or methyl; R.sup.36 is hydrogen or methyl; and R.sup.38 is (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.

28. The method of claim 27 wherein R.sup.37 is hydrogen or methoxy and R.sup.38 is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluromethoxy; cyano; nitro; trifluromethyl; 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.37 is in the 3-position.

29. The method of claim 27 wherein R.sup.37 is hydrogen and R.sup.38 is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R.sup.2 SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl.

30. The method of claim 27 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is hydrogen.

31. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is methylthio.

32. The method of claim 27 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluromethyl.

33. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluoromethyl.

34. The method of claim 27 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is ClCH.sub.2 SO.sub.2 --.

35. The method of claim 27 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is fluorine.

36. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is chlorine.

37. The method of claim 27 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2 --.

38. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is n--C.sub.3 H.sub.7 SO.sub.2.

39. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2.

40. The method of claim 27 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is C.sub.2 H.sub.5 CO.sub.2.

41. The method of claim 27 wherein R.sup.37 is hydrogen.

42. The method of claim 29 wherein R.sup.31 and R.sup.32 are both hydrogen or both methyl and R.sup.33, R.sup.34, R.sup.35 and R.sup.36 are hydrogen.

43. The method of claim 42 wherein R.sup.38 is --SO.sub.2 CH.sub.3.

44. The method of claim 42 wherein R.sup.38 is --SO.sub.2 CH.sub.2 Cl.

45. The method of claim 42 wherein R.sup.38 is trifluoromethyl.

46. The method of claim 27 wherein R.sup.31 as methyl, R.sup.32 is methyl; R.sup.32 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is cyano.

47. An herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione compound of the formula ##STR99## wherein R.sup.31 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.32 is hydrogen or C.sub.1 -C.sub.4 alkyl; or

R.sup.31 and R.sup.32 together are alkylene having 3 to 6 carbon atoms;

R.sup.33 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.34 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.35 is hydrogen or C.sub.1 -C.sub.4 alkyl;

R.sup.36 is hydrogen or C.sub.1 -C.sub.4 alkyl; and

R.sup.37 is hydrogen or 3--C.sub.1 -C.sub.4 alkoxy; and

R.sup.38 is (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 its herbicidally effective salts and an inert carrier therefor.

48. The herbicidal composition of claim 47 wherein R.sup.31 is hydrogen or methyl; R.sup.32 is hydrogen or methyl; R.sup.33 is hydrogen or methyl; R.sup.34 is hydrogen or methyl; R.sup.35 is hydrogen or methyl; R.sup.36 is hydrogen or methyl; and R.sup.38 is (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (b 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.

49. The herbicidal composition of claim 48 wherein R.sup.37 is hydrogen.

50. The herbicidal composition of claim 48 wherein R.sup.37 is hydrogen or methoxy and R.sup.38 is 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.37 is in the 3-position.

51. The herbicidal composition of claim 48 wherein R.sup.37 is hydrogen and R.sup.38 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.

52. The herbicidal composition of claim 48 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is hydrogen.

53. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is methylthio.

54. The herbicidal composition of claim 48 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluoromethyl.

55. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is trifluoromethyl.

56. The herbicidal composition of claim 48 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is chlorine.

57. The herbicidal composition of claim 48 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is fluorine.

58. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is chlorine.

59. The herbicidal composition of claim 48 wherein R.sup.31 is methyl; R.sup.32 is methyl; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2 --.

60. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is n--C.sub.3 H.sub.7 SO.sub.2.

61. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is CH.sub.3 SO.sub.2.

62. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R.sup.35 is hydrogen; R.sup.36 is hydrogen; R.sup.37 is hydrogen; and R.sup.38 is C.sub.2 H.sub.5 SO.sub.2.

63. The herbicidal composition of claim 48 wherein R.sup.31 is methyl, R.sup.32 is methyl, R.sup.33 is hydrogen, R.sup.34 is hydrogen, R.sup.35 is hydrogen, R.sup.36 is hydrogen, R.sup.37 is hydrogen and R.sup.38 is ClCH.sub.2 SO.sub.2.

64. The composition of matter of claim 49 wherein R.sup.31 and R.sup.32 are both hydrogen or both methyl and R.sup.33, R.sup.34, R.sup.35 and R.sup.36 are hydrogen.

65. The composition of matter of claim 64 wherein R.sup.38 is --SO.sub.2 CH.sub.3.

66. The composition of matter of claim 64 wherein R.sup.38 is --SO.sub.2 CH.sub.2 Cl.

67. The composition of matter of claim 64 wherein R.sup.38 is trifluoromethyl.

68. The composition of matter of claim 64 wherein R.sup.38 is --SO.sub.2 CH.sub.3.

69. The herbicidal composition of claim 48 wherein R.sup.31 is hydrogen; R.sup.32 is hydrogen; R.sup.33 is hydrogen; R.sup.34 is hydrogen; R hydrogen; R.sup.37 is hydrogen; and R.sup.38 is cyano.

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Deloitte
US Army

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