Patent EA-000868-B1 (EA)
Title: Pyridazin-3-one derivatives, their use as herbicides, and intermediates for their production
Inventor: KATAYMA TADASHI
IPC: C07D237/14
Filed: 1996-08-19
Abstract: A compound of the formula:   wherein R<1> is C1-C3 haloalkyl; R<2> and R<3> are the same or different and are hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or C1-C3 alkoxy C1-C3 alkyl; and Q is [Q-l], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula:   wherein in formula Q-1 X is H, F or Cl, Y is Cl, F or Br, R<1> is CF3 R<2>  is H or CH3, R<3> is H or Ch3, B is hydrogen, nitro, OR<10>, SR<10>, SO2OR<10>, N(R<11>)R<12>, SO2N(R<11>)R<12>, NR<11>(COR<13>), NR<11>(SO2R<14>), N(SO2R<14>) (SO2R<15>), N(SO2R<14>)(COR<13>), NHCOOR<13>, COOR<10>, CSN(R<11>)R<12>, COR<16>, CR<17>=CR<18>COR<16>, CR<17>=CR<18>COOR<13>, CR<17>=CR<18> CON(R<11>)R<12>, CR<17>=NOR<33>, CR<17>(Z2R<34>)2, OCO2R<19>, or OCOR<19>; wherein R<10> is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonyl C1-C6 alkyl, (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkyl}carbonyl C1-C6 alkyl, (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl, CH2CON (R<11>)R<12>, CH2COON(R<11>)R<12>, CH(C1-C4 alkyl)CON(R<11>)R<12>, CH(C1-C4 alkyl)COON(R<11>)R<12>, {(C1-C6 alkoxy)carbonyl (C1-C6 alkyl}oxycarbonyl (C1-C6 alkyl, or hydroxy (C1-C6 alkyl; R<11> and R<12> are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl (C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy) C1-C4 alkoxy} carbonyl C1-C6 alkyl, or R<11> and R<12> are combined together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R<13> is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, or C3-C8 alkenyl; R<14> and R<15> are independently C1-C6 alkyl, C1-C6 haloalkyl, or phenyl optionally substituted with methyl or nitro; R<16> is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C8-alkoxyalkyl, or hydroxy C1-C6 alkyl; R<17> and R<18> are independently hydrogen or C1-C6 alkyl; R<19> is C1-C6 alkyl; R<33> is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, or (C1-C6 alkoxy)carbonyl C1-C6 alkyl; R<34> is C1-C6 alkyl, or two R<34>,s are combined together to form (CH2)2 or (CH2)3; and in formula Q-2 X is H or F, Z<1> is O or S, N is 0 or 1, R<1> is CF3, R<2> is H or CH3, R<3> is H or CH3,  R<4> is H, R<5> is propargyl or butyl; in formula Q-3 X is F, Y is Cl, Z<2> is O, R<1> is CF3, R<2> is CH3, R<3> is H, R<6> is CH3; in formula Q-4 X is F, Y is Cl, R<1> is CF3, R<2> is CH3, R<3> is H, R<7> is CH3, R<8> is CH3, COOCH3, CH2OH or CH2OCOCH3, W is H, Cl or Br. 2. A compound according to claim 1, wherein R<1> is trifluoromethyl. 3. A compound according to claim 1, wherein R<2> is hydrogen or C1-C3 alkyl, and R<3> is hydrogen or C1-C3 alkyl. 4. A compound according to claim 1, wherein R<1> is trifluoromethyl, R<2> is hydrogen or C1-C3 alkyl, and R<3> is hydrogen or C1-C3 alkyl. 5. A compound according to claim 1,2,3, or 4, wherein Q is [Q-1]. 6. A compound according to claim 1, 2, 3, or 4, wherein Q is [Q-2]. 7. A compound according to claim 1, 2, 3, or 4, wherein Q is [Q-3]. 8. A compound according to claim 1, 2, 3, or 4, wherein Q is [Q-4]. 9. A compound according to claim 5, wherein B is OR<10>. 10. A compound according to claim 5, wherein B is SR<10>. 11. A compound according to claim 5, wherein B is N(R<11>)R<12>. 12. A compound according to claim 5, wherein B is NR<11>(SO2R<14>). 13. A compound according to claim 5, wherein B is COOR<10>. 14. A compound according to claim 5, wherein X is fluorine and Y is chlorine. 15. A compound according to claim 5, wherein X is fluorine, Y is chlorine, and B is OR<10>. 16. A compound according to claim 6, wherein Z<1> is oxygen and n is 1. 17. A compound according to claim 1, which is 7-fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-631). 18. A compound according to claim 1, which is 7-fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-251). 19. A compound according to claim 1, which is 6-(5-trifluoromethyl-3 pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-583). 20. A compound according to claim I, which is 6-(4-methyl-5-trifluoro methyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-203). 21. A compound according to claim 1, which is 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifiuorometbylpyridazin-3-one (compound 1-476). 22. A compound according to claim 1, which is 2-(4-chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-474). 23. A compound according to claim 1, which is 2-(4-chloro-2-fluoro-5-ethoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-475). 24. A compound according to claim 1, which is 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethyl pyridazin-3-one (compound 1-486). 25. A compound according to claim 1, which is methyl 2-chloro-4-fluoro 5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-495). 26. A compound according to claim 1, which is ethyl 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-496). 27. A compound according to claim 1, which is propyl 2-chloro-4-fluoro 5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-497). 28. A compound according to claim 1, which is isopropyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-500). 29. A compound according to claim 1, which is butyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-498). 30. A compound according to claim 1, which is pentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-499). 31. A compound according to claim 1, which is cyclopentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound 1-501). 32. A compound according to claim 1, which is ethyl 2-{2-chloro-4-fluoro-5-(4-me thyl-5-trifluoromethyl-3-p yridazinon-2-y l)phenoxy} propionate (compound 1-504). 33. A compound according to claim 1, which is methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-y l)phenoxy}propionate (compound 1-503). 34. A compound according to claim 1, which is ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate (compound 1-577). 35. A compound according to claim 1, which is methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate (compound 1-576). 36. A compound according to claim 1. which is ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate (compound 1-585). 37. A compound according to claim 1, which is methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate (compound 1-584). 38. A compound according to claim 1, which is methyl 2-{2-chloro-4-fluoro-5-(5-trifluoro methy 1-3-pyridazinon-2-yl)phenoxy}propionate (compound 1-1140). 39. A compound according to claim 1, which is ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate (compound 1-1141). 40. A compound according to claim 1, which is ethyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate (compound 1-1214). 41. A compound according to claim 1, which is methyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate (compound 1-1213). 42. A compound according to claim 1, which is ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate (compound 1-1222). 43. A compound according to claim 1, which is methyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate (compound 1-1221). 44. A compound according to claim 1, which is isopropyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate (compound 1-1226). 45. A compound according to claim 1. which is ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate (compound 1-420). 46. A compound according to claim 1, which is ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate (compound 1-1057). 47. A compound according to claim 1, which is N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl} methanesulfonamide (compound 1-367). 48. A compound according to claim 1, which is N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}chloromethanesulfonamide (compound 1-369). 49. A compound according to claim 1, which is N-{2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide (compound 1-398). 50. A compound according to claim 1, which is methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate (compound 1-641). 51. A compound according to claim 1, which is ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate (compound 1-642). 52. A compound according to claim 1, which is ethyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate (compound 1-621). 53. A compound according to claim 1, which is isopropyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate (compound 1-625). 54. A compound according to claim 1, which is 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-6-methyl-5-trifluorometbylpyridazin-3-one (compound 1-1441). 55. A herbicidal composition comprising a herbicidally effective amoun