Patent EA-001064-B1 (EA)
Title: N-([1,2,4] triazoloazinyl)benzenessulfonamide and pyridinesulfonamide compounds and their use as herbecides
Inventor: JOHNSON TIMOTHY C
IPC: A01N43/90
Filed: 1997-09-23
Abstract: 1. N-(triazolasinyl) arylsulphonamide of formula I   wherein X is N or C-Y; W is O(C1-C3 alkyl), Cl, Br, F or H; Y is H, OCH3, F, Cl, Br, I or CH3, optionally containing as substituents up to 3 atoms of fluoro;  Z is O(C1-C3 alkyl), H, F, Cl, Br, I, S(C1-C3 alkyl) or CH3, optionally containing as substituents up to 3 atoms of fluoro; provided that at least one of W and Z is O(C1-C3 alkyl); Q is C-H or N; A is F, Cl, Br, I or CO2(C1-C4 alkyl) or is (C1-C3 alkyl), O(C1-C4 alkyl), O(C3-C4 alkenyl), O(C3-C4 alkynyl) or S(C1-C3 alkyl), each of them is optionally substituted with one substituent, which is O(C1-C3 alkyl), S(C1-C3 alkyl), chloro, bromo or cyano, or atoms of fluoro up to the greatest possible amount of them, or is a fragment of 2-methyl-1,3-dioxolane-2-yl, and when Q is N, H; B is H, F, Cl, Br, I, NO2, CN, CO2(C1-C4 alkyl), NH(C1-C3 alkyl) or N(C1-C3 alkyl)2, or is (C1-C3 alkyl), O(C1-C4 alkyl), O(C3-C4 alkenyl), O(C3-C4 alkynyl) or S(C1-C3 alkyl), SO(C1-C3 alkyl), SO2(C1-C3 alkyl), S(C3-C4 alkenyl), SO(C3-C4 alkenyl), SO2(C3-C4 alkenyl), S(C3-C4 alkynyl), SO(C3-C4-alkynyl) or SO2(C3-C4 alkynyl), each of them is optionally substituted with one substituent, which is O(C1-C3 alkyl), S(C1-C3 alkyl), chloro, bromo or cyano, or atoms of fluoro up to the greatest possible amount of them; provided that A and B simultaneously are not hydrogen; D is H, F, Cl, Br, I, (C1-C3 alkyl), OCH3, OC2H5, CH2F, CHF2 or CF3; or B and D taken together are a fragment of formula O-CH2-O, optionally substituted with one or two atoms of F or CH3; T is H, SO2R, C(O)R, C(O)OR, C(O)NR'2 or CH2CH2C(O)OR;  R is C1-C4alkyl, C3-C4alkenyl, or C3-C4alkynyl, each of them is optionally substituted with up to two substituents, which are chloro, bromo, O(C1-C4 alkyl) or phenyl and is optionally substituted with atoms of fluoro up to the greatest possible amount of them; and R' is H, C1-C4alkyl, C3-C4alkenyl, or C3-C4alkynyl; and when T is H, their agriculturally acceptable salts. 2. A compound according to claim 1 wherein T is hydrogen. 3. A compound according to claim 1 wherein X is N and Q is C-H. 4. A compound according to claim 1 wherein W is methoxy and Z is methoxy, fluoro, chloro or bromo.  5. A compound according to claim 1 wherein A is methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethoxy, methoxyethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, l-(fluoromethyl)-2-fluoroethoxy, trifluoromethoxy, chloro, or fluoro; B represents hydrogen, methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethyl, methylthio, methyl, trifluoromethyl, trifluoromethoxy, fluoro, chloro, or methoxycarbonyl; and D represents hydrogen, fluoro, chloro, bromo, or methyl. 6. A compound according to claim 5 wherein B represents methoxy and D represents hydrogen; A represents methoxy and D represents hydrogen, methyl, or chloro; or B represents trifluoromethyl and D represents hydrogen. 7. A compound according to claim 1 wherein Q represents C-H and A represents methoxy, ethoxy, propoxy, or 1-methylethoxy, methoxymethoxy, methoxyethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, or 1-(fluoromethyl)-2-fluoroethoxy; B represents hydrogen, methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethyl, trifluoromethyl, fluoro, chloro, or methoxycarbonyl; and D represents hydrogen, chloro, or methyl; or wherein Q represents N and A represents methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethoxy, methoxyethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, or 1-(fluoromethyl)-2-fluoroethoxy; B represents hydrogen, methoxy, ethoxy, propoxy, 1-methylethoxy, trifluoromethyl, or methoxycarbonyl; and D represents hydrogen or methyl. 8. A compound according to claim 1 which is selected from the group: 2-methoxy-6-(trifluoromethyl)-N-(8-chloro-5-methoxy[1,2,4]-triazol[l,5-c]pyrimidin-2-yl)benzenesulfonamide; 2,6-dimethoxy-N-(5,8-dimethoxy[l,2,4]triazol[l,5-c]pyrimidin-2-yl)benzenesulfonamide; 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[l,2,4]triazol[1,5-a]pyridin-2-yl]benzenesulfonamide; 2-methoxy-5-methyl-N-(5,8-dimethoxy[l,2,4]triazol[1,5-c]pyrimidin-2-yl)benzenesulfonamide; 5-chloro-2-methoxy-N-(5,8-dimethoxy[1,2,4]triazol[1,5-c]pyrimidin-2-yl)benzenesulfonamide; 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[l,2,4]triazol[l,5-c]pyrimidin-2-yl)pyridine-3-sulfonamide; 2-(2-fluoroethoxy)-6-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazol[1,5-c]pyrimidin-2-yl)benzenesulfonamide; 2-(2-chloroethoxy)-6-(trifluoromethyl)-N-(5,8-dimethoxy[l,2,4]triazol[1,5-c]pyrimidin-2-yl)benzenesulfonamide; 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazol[1,5-c]pyrimidin-2-yl)benzenesulfonamide, and 2-(l-fluoromethyl-2-fluoroethoxy)-6-(trifluoromethyl)-N-(5,8-dimethoxy[l,2,4]triazol[l,5-c]pyrimidin-2-yl)benzenesulfonamide. 9. A composition characterized by comprising an herbicidal effective amount of N-(triazolazinyl)arylsulfonamide compound of any one of claims 1-8 in admixture with an agriculturally acceptable adjuvant or carrier. 10. A method of controlling undesirable vegetation which is characterized by applying to the vegetation or to the locus thereof an herbicidally effective amount of N-(triazolazinyl)-arylsulfonamide compound of any one of claims 1-8. 11. A sulfonylchloride compound of the formula:    wherein Q represents N or CH; A represents F, Cl, Br, or I, or CO2(C1-C4alkyl) or represents C1-C3alkyl, O(C1-C4alkyl), O(C3-C4alkenyl), O(C3-C4alkynyl), or S(C1-C3alkyl) each optionally substituted with one substituent which is a group O(C1-C3alkyl), S(C1-C3alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, or represents a 2-methyl-1,3-dioxolan-2-yl moiety; B represents H, F, Cl, Br, I, NO2 , CN, CO2(C1-C4 alkyl), NH(C1-C3 alkyl) or N(C1-C3 alkyl)2, or is O(C1-C4 alkyl), O(C3-C4 alkenyl), O(C3-C4 alkynyl), C1-C3 alkyl, S(C1-C3 alkyl), SO(C1-C3 alkyl), SO2(C1-C3 alkyl), S(C3-C4 alkenyl), SO(C3-C4 alkenyl), SO2(C3-C4 alkenyl), S(C3-C4 alkynyl), SO(C3-C4-alkynyl) or SO2(C3-C4 alkynyl), each of them is optionally substituted with one substituent, which is O(C1-C3 alkyl), S(C1-C3 alkyl), chloro, bromo or cyano, or atoms of fluoro up to the greatest possible amount of them;  D represents H, F, Cl, Br, I, C1-C3 alkyl, OCH3, OC2H5, CH2F, CHF2 or CF3; or B and D taken together are a fragment of formula O-CH2-O, optionally substituted with one or two atoms of F or radicals CH3;  with proviso that when Q=N, then at least one of A and B represents O(C1-C4 alkyl), O(C3-C4 alkenyl), or O(C3-C4 alkynyl), each of them optionally substituted with one substituent which represents O(C1-C3alkyl), S(C1-C3alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, and with proviso that when Q=CH, A represents OCH2CF3, OCH2CHF2, OCH2CH2F, OCH2CF2CF3, or OCH(CH2F)2, B represents CF3  and D represents H. 12. A compound according to claim 11 wherein Q represents N, A represents methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethoxy, methoxyethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, 1-(fluoromethyl)-2-fluoroethoxy, trifluoromethoxy, chloro, or fluoro; B represents hydrogen, methoxy, ethoxy, propoxy, 1-methylethoxy, methoxy-methyl, methylthio, methyl, trifluoromethyl, trifluoromethoxy, fluoro, chloro, or methoxycarbonyl; and D represents hydrogen, fluoro, chloro, bromo, or methyl. 13. A compound according to claim 12 wherein A represents methoxy, ethoxy, propoxy, 1-methylethoxy, methoxymethoxy, methoxyethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, or 1-(fluoromethyl)-2-fluoroethoxy; B represents hydrogen, methoxy, ethoxy, propoxy, l-methylethoxy, trifluoromethyl, or methoxycarbonyl; and D represents hydrogen or methyl. 14. 2-amino[l,2,4]triazol[1,5-c]pyrimidine compound of the formula:   wherein W represents O(C1-C3 alkyl), Cl, Br, F, or H; and Z represents O(C1-C3 alkyl), H, F, Cl, Br, I, S(C1-C3 alkyl), or CH3 optionally substituted with up to three fluorine atoms; with the proviso that at least one of W and Z represents O(C1-C3 alkyl). 15. A compound according to claim 14 wherein W represents methoxy and Z represents methoxy, fluoro, chloro, or bromo.