Claims for Patent: 5,006,158

Summary for Patent: 5,006,158

Title:	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
Abstract:	Compounds of the formula wherein R1 is hydrogen or C1-C4 alkyl; R2 is hydrogen, C1-C4 alkyl or wherein Ra is C1-C4 alkyl; R1 and R2 together are alkylene having 3 to 6 carbon atoms; R3 is hydrogen or C1-C4 alkyl; R4 is hydrogen or C1-C4 alkyl; R5 is hydrogen or C1-C4 alkyl; R6 is hydrogen or C1-C4 alkyl; R7 is hydrogen or 3-C1-C4 alkoxy; and R8 is (1) hydrogen; (2) halogen; (3) C1-C4 alkyl; (4) C1-C4 alkoxy; (5) OCF3; (6) cyano; (7) nitro; (8) C1-C4 haloalkyl; (9) RbSOn- wherein n is the integer 0, 1 or 2; and Rb is (a) C1-C4 alkyl; (b) C1-C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) -NRcRd wherein Rc and Rd independently are hydrogen or C1-C4 alkyl; (11) ReC(O)- wherein Re is C1-C4 alkyl or C1-C4 alkoxy; or (12) SO2NRcRd wherein Rc and Rd are as defined, their use as herbicides and herbicidal compositions containing the compounds.
Inventor(s):	Charles G. Carter, David L. Lee, William J. Michaely, Gary W. Kraatz
Assignee:	Zeneca Inc , Syngenta Crop Protection LLC
Application Number:	US07/128,128
Patent Claims:	1. Compounds of the formula ##STR97## wherein R31 is hydrogen or C1 -C4 alkyl;R32 is hydrogen or C1 -C4 alkyl ; or R31 and R32 together are alkylene having 3 to 6 carbon atoms; R33 is hydrogen or C1 -C4 alkyl; R34 is hydrogen or C1 -C4 alkyl; R35 is hydrogen or C1 -C4 alkyl; R36 is hydrogen or C1 -C4 alkyl; and R37 is hydrogen or 3-C1 -C4 alkoxy; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1 -C4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined, and their herbicidally effective salts. 2. The compounds of claim 1 wherein R31 is hydrogen or methyl; R32 is hydrogen or methyl; R33 is hydrogen or methyl; R34 is hydrogen or methyl; R35 is hydrogen or methyl; R36 is hydrogen or methyl; R37 is hydrogen or 3-C1 -C4 alkoxy; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1 -C4 alkoxy; (5)trifluoromethoxy; (6) cyano; (7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined. 3. The compounds of claim 2 wherein R37 is hydrogen or 3-methoxy and R38 is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; Rb SOn -- wherein n is the integer 2 and Rb is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; Re C(O)-- where Re is C1 -C4 alkyl or C1 -C4 alkoxy or SO2 NRc Rd wherein Rc and Rd are as defined and R37 is in the 3-position. 4. The compounds of claim 2 wherein R37 is hydrogen and R38 is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or Rb SO2 wherein Rb is C1 -C4 alkyl or C1 -C4 haloalkyl. 5. The compound of claim 2 wherein R31 is methyl; R32 is methyl, R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is hydrogen. 6. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is methylthio. 7. The compound of claim 2 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluoromethyl. 8. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluoromethyl. 9. The compound of claim 2 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is ClCH2 SO2 --. 10. The compound of claim 2 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is fluorine. 11. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is chlorine. 12. The compound of claim 2 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2 --. 13. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is n-C3 H7 SO2. 14. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2. 15. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is C2 H5 SO2. 16. The compounds of claim 2 wherein R37 is hydrogen. 17. The compounds of claim 4 wherein R31 and R32 are both hydrogen or both methyl and R33, R34, R35 and R36 are hydrogen. 18. The compounds of claim 4 wherein R38 is --SO2 CH3. 19. The compounds of claim 4 wherein R38 is --SO2 CH2 Cl. 20. The compounds of claim 4 wherein R38 is trifluoromethyl. 21. The compounds of claim 4 wherein R38 is --SO2 CH3. 22. The compounds of claim 4 wherein R38 is chlorine. 23. The compounds of claim 4 wherein R38 is --SO2 CH2 Cl. 24. The compounds of claim 4 wherein R38 is --SO2 --n--C3 H7. 25. The compound of claim 2 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen, R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 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 R31 is hydrogen or C1 -C4 alkyl;R32 is hydrogen or C1 -C4 alkyl; or R31 and R32 together are alkylene having 3 to 6 carbon atoms; R33 is hydrogen or C1 -C4 alkyl; R34 is hydrogen or C1 -C4 alkyl; R35 is hydrogen or C1 -C4 alkyl; R36 is hydrogen or C1 -C4 alkyl; and R37 is hydrogen or 3-C1 -C4 alkoxy; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1 -C4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined, or its herbicidally effective salts. 27. The method of claim 26 wherein R31 is hydrogen or methyl; R32 is hydrogen or methyl; R33 is hydrogen or methyl; R34 is hydrogen or methyl; R35 is hydrogen or methyl; R36 is hydrogen or methyl; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1 -C4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C.sub. 1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined. 28. The method of claim 27 wherein R37 is hydrogen or methoxy and R38 is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluromethoxy; cyano; nitro; trifluromethyl; Rb SOn -- wherein n is the integer 2 and Rb is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; Re C(O)-- where Re is C1 -C4 alkyl or C1 -C4 alkoxy or SO2 NRc Rd wherein Rc and Rd are as defined and R37 is in the 3-position. 29. The method of claim 27 wherein R37 is hydrogen and R38 is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R2 SO2 wherein Rb is C1 -C4 alkyl. 30. The method of claim 27 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is hydrogen. 31. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is methylthio. 32. The method of claim 27 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluromethyl. 33. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluoromethyl. 34. The method of claim 27 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is ClCH2 SO2 --. 35. The method of claim 27 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is fluorine. 36. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is chlorine. 37. The method of claim 27 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2 --. 38. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is n--C3 H7 SO2. 39. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2. 40. The method of claim 27 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is C2 H5 CO2. 41. The method of claim 27 wherein R37 is hydrogen. 42. The method of claim 29 wherein R31 and R32 are both hydrogen or both methyl and R33, R34, R35 and R36 are hydrogen. 43. The method of claim 42 wherein R38 is --SO2 CH3. 44. The method of claim 42 wherein R38 is --SO2 CH2 Cl. 45. The method of claim 42 wherein R38 is trifluoromethyl. 46. The method of claim 27 wherein R31 as methyl, R32 is methyl; R32 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is cyano. 47. An herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione compound of the formula ##STR99## wherein R31 is hydrogen or C1 -C4 alkyl;R32 is hydrogen or C1 -C4 alkyl; or R31 and R32 together are alkylene having 3 to 6 carbon atoms; R33 is hydrogen or C1 -C4 alkyl; R34 is hydrogen or C1 -C4 alkyl; R35 is hydrogen or C1 -C4 alkyl; R36 is hydrogen or C1 -C4 alkyl; and R37 is hydrogen or 3--C1 -C4 alkoxy; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1-C 4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined, or its herbicidally effective salts and an inert carrier therefor. 48. The herbicidal composition of claim 47 wherein R31 is hydrogen or methyl; R32 is hydrogen or methyl; R33 is hydrogen or methyl; R34 is hydrogen or methyl; R35 is hydrogen or methyl; R36 is hydrogen or methyl; and R38 is (1) hydrogen; (2) halogen; (3) C1 -C4 alkyl; (4) C1 -C4 alkoxy; (5) trifluoromethoxy; (6) cyano; (b 7) nitro; (8) C1 -C4 haloalkyl; (9) Rb SOn -- wherein n is the integer 0, 1 or 2; and Rb is (a) C1 -C4 alkyl; (b) C1 -C4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; (11) Re C(O)-- wherein Re is C1 -C4 alkyl or C1 -C4 alkoxy; or (12) SO2 NRc Rd wherein Rc and Rd are as defined. 49. The herbicidal composition of claim 48 wherein R37 is hydrogen. 50. The herbicidal composition of claim 48 wherein R37 is hydrogen or methoxy and R38 is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; Rb SOn -- wherein n is the integer 2 and Rb is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NRc Rd wherein Rc and Rd independently are hydrogen or C1 -C4 alkyl; Re C(O)-- where Re is C1 -C4 alkyl or C1 -C4 alkoxy or SO2 NRc Rd wherein Rc and Rd are as defined and R37 is in the 3-position. 51. The herbicidal composition of claim 48 wherein R37 is hydrogen and R38 is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or Rb SO2 wherein Rb is C1 -C4 alkyl. 52. The herbicidal composition of claim 48 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is hydrogen. 53. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is methylthio. 54. The herbicidal composition of claim 48 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluoromethyl. 55. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is trifluoromethyl. 56. The herbicidal composition of claim 48 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is chlorine. 57. The herbicidal composition of claim 48 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is fluorine. 58. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is chlorine. 59. The herbicidal composition of claim 48 wherein R31 is methyl; R32 is methyl; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2 --. 60. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is n--C3 H7 SO2. 61. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is CH3 SO2. 62. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R35 is hydrogen; R36 is hydrogen; R37 is hydrogen; and R38 is C2 H5 SO2. 63. The herbicidal composition of claim 48 wherein R31 is methyl, R32 is methyl, R33 is hydrogen, R34 is hydrogen, R35 is hydrogen, R36 is hydrogen, R37 is hydrogen and R38 is ClCH2 SO2. 64. The composition of matter of claim 49 wherein R31 and R32 are both hydrogen or both methyl and R33, R34, R35 and R36 are hydrogen. 65. The composition of matter of claim 64 wherein R38 is --SO2 CH3. 66. The composition of matter of claim 64 wherein R38 is --SO2 CH2 Cl. 67. The composition of matter of claim 64 wherein R38 is trifluoromethyl. 68. The composition of matter of claim 64 wherein R38 is --SO2 CH3. 69. The herbicidal composition of claim 48 wherein R31 is hydrogen; R32 is hydrogen; R33 is hydrogen; R34 is hydrogen; R hydrogen; R37 is hydrogen; and R38 is cyano.