Claims
- 1. A Compound of the formula (I) or a salt thereof, in whichR1 is H, (C1-C6)alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkoxy, (C3-C6)cycloalkyl, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkyl, (c1-C4)-haloalkyl and (C1-C4)alkoxy, R2 is H, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfynyl, (C1-C4)alkylsulfonyl, nitro, cyano and thiocyanato, or (C1-C6)alkoxy or (C1C6)alkylthio, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1C4)alkylthio, aryl and substituted aryl, (C3-C7)-cycloalkyl or (C3-C7)cycloalkoxy, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl and halogen, or aryl, substituted aryl, or a radical of the formula NRaRb, R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C4)-alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf, Ra, Rb, Rc, Rd, Re and Rf independently of one another are H, (C1-C4)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, [(C1-C4)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs Ra and Rb, Rc and Rd or Re and Rf together with the N atom linking them are a heterocyclic saturated or unsaturated ring selected from the group consisting of pyrrole, imidazole, pyrazole, triazole, pyrrazolone, oxazole, oxazolene, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine, R4 is H or (C1-C4)alkyl, m is 0 or 1, n is 0, 1 or 2, A is a radical of the formula X and Y independently of one another are H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- disubstituted by (C1-C3)-alkoxy or (C1-C3)alkylthio, or a radical of the formula NR5R6, (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)alkynyloxy, R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)alkenyl, W is O or S, Z is CH, X1 is CH3, OCH3, OC2H5 or OCF2H, Y1 is —O— or —CH2—, Y3 is H or CH3, Y5 is CH3, C2H5 or Cl.
- 2. A compound or a salt thereof, as claimed in claim 1, whereinR1 is H, (C1-C4)alkyl which is unsubstituted or substituted by 1 to 3 radicals selected from the group comprising halogen or by (C1-C2)alkoxy or (C3-C5)cycloalkyl, or R2 is H, (C1-C4)alkyl which is unsubstituted or substituted by one or more halogen atoms or by (C1-C2)alkoxy, or (C2-C4)alkenyl, (C2-C3)alkynyl, (C3-C5)cycloalkyl, (C1-C4)alkoxy which is unsubstituted or substituted by one or more halogen atoms or by phenyl, or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1-C4)alkyl, or R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, (C1-C3)alkoxy or nitro, or A is a radical of the formula in which one of the radicals X and Y is (C1-C3)-alkyl, (C1-C3)alkoxy, (C1-C3)haloalkyl, (C1-C3)-haloalkoxy or [(C1-C2)alkoxy]-(C1-C2)alkyl and the other radical Y or X is (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, where each of the last-mentioned 3 radicals is unsubstituted or mono- or polysubstituted by halogen or mono- or disubstituted by (C1-C3)alkoxy or (C1-C3)-alkylthio, or halogen, or a radical of the formula NR5R6 in which R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)-alkenyl, or (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)alkynyloxy.
- 3. A compound or a salt thereof, as claimed in claim 1, whereinR1 is H, (C1-C4)alkyl, (C1-C4)haloalkyl or [(C1-C2)-alkoxy]-(C1-C2)alkyl, R2 is H, (C1-C4)alkyl, halo-(C1-C4)alkyl, (C2-C4)-alkenyl, (C2-C4)alkynyl, (C1-C4)alkoxy, [(C1-C2)alkoxy]-(C1-C2)alkyl, (C3-C5)cycloalkyl or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1-C4)-alkyl, R3 is (C1-C4)alkyl, halogen, nitro or (C1-C4)alkoxy and n is 0 or 1.
- 4. A compound or a salt thereof, according to claim 1, whereinone of the radicals X or Y is (C1-C2)alkyl, (C1-C2)-alkoxy or OCF2H and the other radical Y or X is (C1-C2)alkyl, (C1-C2)alkoxy, halogen, OCF2H, OCH2CF3 or CF3.
- 5. A herbicidal or plant-growth-regulating agent, which comprises at least one compound of the formula (I) or a salt thereof as claimed in claim 1,and formulation auxiliaries which are customary in crop protection.
- 6. A method of controlling harmful plants or for regulating the growth of plants, which comprises applying an effective amount of at least one compound of the formula (I) or a salt thereof as claimed in claim 1, to the harmful plants or plants, to the seeds of these plants, or to the area on which the plants grow.
- 7. A method of controlling harmful plants wherein a compound of the formula (I) or a salt thereof as claimed in claim 1 is used as a herbicide.
- 8. A compound or a salt thereof, as claimed in claim 1, whereinR1 is H, CH3 or C2H5, R2 is H, (C1-C4)-alkyl, (C1-C2)-haloalkyl, vinyl, cyclopropyl, cyclobutyl, (C1-C2)-alkoxy or N(CH3)2, R3 is (C1-C4)-alkyl, halogen, nitro or (C1-C4)-alkoxy, n is 0 or 1.
- 9. A compound or a salt thereof, as claimed in claim whereinR3 is (C1-C4)-alkyl, halogen, nitro or (C1-C4)-alkoxy, R4 is H, A is a radical of the formula X is (C1-C2)-alkyl or (C1-C2)-alkoxy, Y is (C1-C2)-alkyl or (C1-C2)-alkoxy, m is 0, and n is 0.
- 10. A compound or a salt thereof, as claimed in claim 9, whereinR2 is H, X is methyl or methoxy, and Y is methyl or methoxy.
- 11. A Compound of the formula (I) or a salt thereof, in whichR1 is H, (C1-C6)alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C6)alkoxy, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)alkoxy, R2 is H, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)-alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfynyl, (C1-C4)alkylsulfonyl, nitro, cyano and thiocyanato, or is (C3-C7)-cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting or (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl and halogen, or aryl, substituted aryl, or a radical of the formula NRaRb, R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C4)alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)-alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf, Ra, Rb, Rc, Rd, Re and Rf independently of one another are H, (C1-C4)alkyl, (C3-C6)alkenyl, (C3-C6)-alkynyl, [(C1-C4)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs Ra and Rb, Rc and Rd or Re and Rf together with the N atom linking them are a heterocyclic saturated or unsaturated ring selected from the group consisting of pyrrole, imidazole, pyrazole, triazole, pyrrazolone, oxazole, oxazolene, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine, R4 is H or (C1-C4)alkyl, m is 0 or 1, n in 0, 1 or 2, A is a radical of the formula X and Y independently of one another are H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono-disubstituted by (C1-C3)-alkoxy or (C1-C3)alkylthio, or a radical of the formula NR5R6, (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)-alkynyloxy, R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)alkenyl, W is O or S, Z is CH, X1 is CH3, OCH3, OC2H5 or OCF2H, Y1 is —O— or —CH2—, Y3 is H or CH3, Y5 is CH3, C2H5, or Cl.
- 12. A compound or a salt thereof, as claimed in claim 11, whereinR1 is H, (C1-C6)alkyl which is unsubstituted or substituted by 1 to 3 radicals selected from the group consisting of halogen or by (C1-C2)alkoxy.
- 13. A compound or a salt thereof, as claimed in claim 11, whereinR2 is H, (C1-C4)alkyl which is unsubstituted or substituted by one or more halogen atoms or by (C1-C2)alkoxy, or (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C5)cycloalkyl or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1-C4)alkyl.
- 14. A compound or a salt thereof, as claimed in claim 11, whereinR3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, (C1-C3)alkoxy or nitro and n is 0, 1 or 2.
- 15. A compound or a salt thereof, as claimed in claim 11, whereinA is a radical of the formula in which one of the radicals X and Y is (C1-C3)-alkyl, (C1-C3)alkoxy, (C1-C3)haloalkyl, (C1-C3)-haloalkoxy or [(C1-C2)alkoxy]-(C1-C2)alkyl and the other radical Y or X is (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, where each of the last-mentioned 3 radicals is unsubstituted or mono- or polysubstituted by halogen or mono- or disubstituted by (C1-C3)alkoxy or (C1-C3)-alkylthio, or halogen, or a radical of the formula NR5R6 in which R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)-alkenyl, or (C3-C5)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)-alkynyloxy.
- 16. A compound or a salt thereof, as claimed in claim 11, whereinR1 is H, (C1-C4)alkyl, (C1-C4)haloalkyl or [(C1-C2)-alkoxy]-(C1-C2)alkyl, R2 is H, (C1-C4)alkyl, halo-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, [(C1-C2)alkoxy]-(C1-C2)alkyl, (C3-C5)cycloalkyl or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1C4)alkyl, R3 is (C1-C4)alkyl, halogen, nitro or (C1-C4)alkoxy and n is 0 or 1.
- 17. A compound or a salt thereof, as claimed in claim 11, whereinone of the radicals X or Y is (C1-C2)alkyl, (C1-C2)alkoxy or OCF2H and the other radical Y or X is (C1-C2)alkyl, (C1-C2)alkoxy, halogen, OCF2H, OCH2CF3 or CF3.
- 18. A compound or a salt thereof, as claimed in claim 12, whereinR2 is H, (C1-C4)alkyl which is unsubstituted or substituted by one or more halogen atoms or by (C1-C2)alkoxy, or (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C5)cycloalkyl or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1-C4)alkyl.
- 19. A compound or a salt thereof, as claimed in claim 18, whereinR3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, (C1-C3)alkoxy or nitro and n is 0, 1 or 2.
- 20. A compound or a salt thereof, as claimed in claim 19, whereinA is a radical of the formula in which one of the radicals X and Y is (C1-C3)-alkyl, (C1-C3)alkoxy, (C1-C3)haloalkyl, (C1-C3)-haloalkoxy or [(C1-C2)alkoxy]-(C1-C2)alkyl and the other radical Y or X is (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, where each or the last-mentioned 3 radicals is unsubstituted or mono- or polysubstituted by halogen or mono- or disubstituted by (C1-C3)alkoxy or (C1-C3)-alkylthio, or halogen, or a radical of the formula NR5R6 in which R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)-alkenyl, or (C3-C5)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)-alkynyloxy.
- 21. A compound or a salt thereof, as claimed in claim 20, whereinR1 is H, (C1-C4)alkyl, (C1-C4)haloalkyl or [(C1-C2)-alkoxy]-(C1-C2)alkyl, R2 is H, (C1-C4)alkyl, halo-(C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, [(C1-C2)alkoxy]-(C1-C2)alkyl, (C3-C5)cycloalkyl or a radical of the formula NRaRb in which Ra and Rb independently of one another are H or (C1-C4)alkyl, R3 is (C1-C4)alkyl, halogen, nitro or (C1-C4)alkoxy and n is 0 or 1.
- 22. A compound or a salt thereof, as claimed in claim 21, whereinone of the radicals X or Y is (C1-C2)alkyl, (C1-C2)alkoxy or OCF2H and the other radical Y or X is (C1-C2)alkyl, (C1-C2)alkoxy, halogen, OCF2H, OCH2CF3 or CF3.
- 23. A Compound of the formula (I) or a salt thereof, as claimed in claim 11in whichR1 is H, (C1-C6)alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkoxy, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkyl, (C1-C4)-haloalkyl and (C1-C4)alkoxy, R2 is H, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)-alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfynyl, (C1-C4)alkylsulfonyl, nitro, cyano and thiocyanato, or is (C3-C7)-cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl and halogen, or phenyl, phenyl substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)haloalkyl, nitro, cyano, (C1-C4)alkoxycarbonyl, (C1-C4)alkanoyl, carbamoyl, mono- and di(C1-C4)alkylaminocarbonyl, mono- and di-(C1-C4)alkylamino, (C1-C4)alkylsulfinyl and (C1-C4)alkylsulfonyl or a radical of the formula NRaRb, R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C4)alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)-alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf, Ra, Rb, Rc, Rd, Re and Rf independently of one another are H, (C1-C4)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, [(C1-C4)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs Ra and Rb, Rc and Rd or Re and Rf together with the N atom linking then are a heterocyclic saturated or unsaturated ring selected from the group consisting of pyrrole, imidazole, pyrazole, triazole, pyrrazolone, oxazole, oxazolene, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine, R4 is H or (C1-C4)alkyl, m is 0 or 1, n is 0, 1 or 2, A is a radical of the formula X and Y independently of one another are H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono-disubstituted by (C1-C3)-alkoxy or (C1-C3)alkylthio, or a radical of the formula NR5R6, (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)alkynyloxy, R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)alkenyl, W is O or S, Z is CH, X1 in CH3, OCH3, OC2H5 or OCF2H, Y1 is —O— or —CH2—, Y3 is R or CH3, Y5 is CH3, C2H5 or Cl.
- 24. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is ethyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 25. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is hydrogen, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 26. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is hydrogen, n is zero, X is ethoxy, y is ethoxy and Z is CH.
- 27. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is isopropyl, n is zero, X is methoxy, Y is methoxy and Z in CH.
- 28. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is CF3, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 29. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is cyclopropyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 30. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is methyl, n is zero, X is methyl, Y is methyl and Z is CH.
- 31. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is dimethylamino, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 32. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is phenyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 33. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is ethenyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 34. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 cyclobutyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 35. A compound as claimed in claim 11, wherein R1 is hydrogen, R2 is methoxymethyl, n is zero, X is methoxy, Y in methoxy and Z is CH.
- 36. A compound as claimed in claim 11, wherein R1 is methyl, R2 is methyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 37. A compound as claimed in claim 11, wherein R1 is methyl, R2 is methyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 38. A compound as claimed in claim 11, wherein R1 is methyl, R2 is CF3, h is zero, X is methoxy, Y is methoxy and Z is CH.
- 39. A compound as claimed in claim 11, wherein R1 is methyl, R2 is isopropyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 40. A compound as claimed in claim 11, wherein R1 is methyl, R2 is methyl, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 41. A compound as claimed in claim 11, wherein R1 is ethyl, R2 in hydrogen, n is zero, X is methoxy, Y is methoxy and Z is CH.
- 42. A compound of the formula 1b wherein hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio, or is C1-C4alkyl mono- or poly-substituted by halogen, R1 is hydrogen or methyl; R2 is methyl or methoxy; R4 is hydrogen, C1-C6alkyl, or C1-C6alkyl that is mono- or polysubstituted by halogen, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy or by C1-C6alkylthio; R6 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C2-C6alkynyl; or is C1-C6alkyl or C3-C6cycloalkyl each substituted by halogen or by C1-C4alkoxy; or is C2-C6alkenyl, or C2-C6 substituted by halogen; or is phenyl, benzyl, naphthyl or OR12, or phenyl, benzyl or naphthyl each substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, nitro, cyano, COOR13, NR15R16, C(O)NR17R18, X1R20, SO2NR21R22 or by X2R23; R12 is C1-C6alkyl, C1-C6haloalkyl, oxetan-3-yl, or C4-C6cycloalkyl, which may for its part be substituted by halogen, C1-C4alkyl or by C1-C4alkoxy; or is phenyl, benzyl or naphthyl, or phenyl, benzyl or naphthyl each substituted by C1-Calkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfinyl, nitro, cyano, COOR27, NR25R26, CONR28R29 or by SO2NR30R14; or is C1-C6alkyl substituted by C1-C4alkoxy, C3-C6cycloalkyl, cyano, COOR24 or by CONR32R33; or is C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, X3N35 or X4R36; R13 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or oxetan-3-yl; R14, R15, R16, R17, R18, R21, R22, R25, R26, R28, R29, R30, R32 and R33 are each independently of the others hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; or R15 or R25 are each independently of the other the groups —C(O)—X5—C1-C4alkyl or —C(O)—C1-C4alkyl, which may for their part be substituted by halogen; or R15 and R16 or R17 and R18 or R21 and R22 or R25 and R26 or R28 and R29 or R30 and R14 or R32 and R33 together form a C4-C5alkylene chain, which may for its part be interrupted by oxygen or by NR19, R19 is hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; R20 and R35 are each independently of the other C1-C4alkyl or C1-C4 haloalkyl; R23 and R36 are each independently of the other C1-C4alkyl substituted by COOR34; R24, R27 and R34 are each independently of the other hydrogen or C1-C4alkyl; X1 and X3 are each independently of the other sulfur, SO or SO2; X2 and X4 are each independently of the other oxygen or sulfur; X5 is oxygen or NR37; and R37 is hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; ora compound of the formula (I) or a salt thereof, in whichR1 is H, (C1-C6)alkyl which in unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkoxy, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)alkoxy, R2 is H, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfynyl, (C1-C4)alkylsulfonyl, nitro, cyano and thiocyanato, or is (C3-C7)-cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl and halogen, or aryl, substituted aryl, or a radical of the formula NRaRb, R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C4)alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)-alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf, Ra, Rb, Rc, Rd, Re and Rf independently of one another are H, (C1-C4)alkyl, (C3-C6)alkenyl, (C3-C6)-alkynyl, [(C1-C4)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs Ra and Rb, Rc and Rd or Re and Rf together with the N atom linking them are a heterocyclic saturated or unsaturated ring selected from th group consisting of pyrrole, imidazole, pyrazole, triazole, pyrrazolone, oxazole, oxazolene, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine, R4 is H or (C1-C4)alkyl, m 0 or 1, n is 0, 1 or 2, A is a radical of the formula X and Y independently of one another are H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- disubstituted by (C1-C3)-alkoxy or (C1-C3)alkylthio, or a radical of the formula NR5R6, (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)alkynyloxy, R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)alkenyl, W is O or S, Z is CH, X1 is CH3, OC3, OC2H5; or OCF2H, Y1 in —O— or —CH2—, Y3 is H or CH3, Y5 is CH3, C2H5 or Cl.
- 43. A compound of the formula 1b wherein R is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio, or is C1-C4alkyl mono- or polysubstituted by halogen; R1 is hydrogen or methyl; R2 is methyl or methoxy; R4 is hydrogen, C1-C6alkyl, or C1-C6alkyl that is mono- or polysubstituted by halogen, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy or by C1-C6alkylthio; R6 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C2-C6alkynyl; or is C1-C6alkyl or C3-C6cycloalkyl each substituted by halogen or by C1-C6alkoxy; or is C2-C6alkenyl, or C2-C6 substituted by halogen; or is phenyl, benzyl, naphthyl or OR12, or phenyl, benzyl or naphthyl each substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, nitro, cyano, COOR13, NR15R16, C(O)NR17R18, SO2N21R22 or by X2R23; R12 is C1-C6alkyl, C1-C6haloalkyl, oxetan-3-yl, or C4-C6cycloalkyl, which may for its part be substituted by halogen, C1-C4alkyl or by C1-C4alkoxy; or is phenyl, benzyl or naphthyl, or phenyl, benzyl or naphthyl each substituted by C1-Calkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfinyl, nitro, cyano, COOR27, NR25R26, CONR28R29, or by SO2NR30R14; or is C1-C6alkyl substituted by C1-C4alkoxy, C3-C6cycloalkyl, cyano, COOR24 or by CONR32R33; or is C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, X3R35 or X4R36; R13 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6 alkynyl or oxetan-3-yl; R14, R15, R16, R17, R18, R21, R22, R25, R26, R28, R29, R30, R32 and R33 are each independently of the others hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; or R15 and R25 are each independently of the other the groups —C(O)—X5— C1-C4alkyl or —C(O)—C1-C4alkyl, which may for their part be substituted by halogen; or R15 and R16 or R17 and R18 or R21 and R22 or R25 and R26 or R28 and R29 or R30 and R14 or R32 and R33 together form a C4-C5alkylene chain, which may for its part be interrupted by oxygen or by NR19, R19 is hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; R20 and R35 are each independently of the other C1-C4alkyl or C1-C4haloalkyl; R23 and R36 are each independently of the other C1-C4alkyl substituted by COOR34; R24, R27 and R36 are each independently of the other hydrogen or C1-C4alkyl; X1 and X3 are each independently of the other sulfur, SO or SO2; X2 and X4 are each independently of the other oxygen or sulfur; X5 is oxygen or NR37; and R37 is hydrogen, C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl; ora compound of the formula (I) or a salt thereof, in whichR1 is H, (C1-C6)alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkoxy, (C3-C6)cycloalkyl, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, (C1-C4)alkyl, (C1-C4)-haloalkyl and (C1-C4)alkoxy, R2 is H, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfynyl, (C1-C4)alkylsulfonyl, nitro, cyano and thiocyanato, or (C1-C6)alkoxy or (C1-C6)alkylthio, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)alkylthio, aryl and substituted aryl, (C3-C7) -cycloalkyl or (C3-C7)cycloalkoxy, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl and halogen, or aryl, substituted aryl, or a radical of the formula NRaRb, R3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)-alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf, Ra, Rb, Rc, Rd, Re and Rf independently of one another are H, (C1-C4)alkyl, (C3-C6)alkenyl, (C3-C6)-alkynyl, [(C1-C4)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs Ra and Rb, Rc and Rd or Re and Rf together with the N atom linking them are a heterocyclic saturated or unsaturated ring selected from the group consisting of pyrrole, imidazole, pyrazole, triazole, pyrrazolone, oxazole, oxazolene, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine, R4 is H or (C1-C4)alkyl, m is 0 or 1, n is 0, 1 or 2, A is a radical of the formula X and Y independently of one another are H, halogen, (C1-C3)alkyl, (C1-C3)alkoxy or (C1-C3)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- disubstituted by (C1-C3)-alkoxy or (C1-C3)alkylthio, or a radical of the formula NR5R6, (C3-C6)cycloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C4)alkenyloxy or (C3-C4)alkynyloxy, R5 and R6 independently of one another are H, (C1-C3)alkyl or (C3-C4)alkenyl, W is O or S, Z is CH, X1 is C3, OCH3, OC2H5 or OCF2H, Y1 is —O— or —CH2—, Y3 is H or CH3, Y5 is CH3, C2R5 or Cl.
- 44. A Compound of the formula (I) or a salt thereof as claimed in claim 14, whereinR3 is (C1-C4)alkyl, (C1-C3)haloalkyl, halogen, NO2, CN, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkylthio, (C1-C3)alkoxy-(C1-C3)alkyl, [(C1-C3)-alkoxy]-carbonyl, (C1-C3)alkylamino, di[(C1-C3)-alkyl]-amino, (C1-C6)-alkylsulfynyl, (C1-C3)-alkylsuflonyl, SO2NRcRd or C(O)NReRf.
- 45. A process for the preparation of a compound or a salt thereof as claimed in any one of claims 1, 11, 42 or 43, which comprisesa) reacting a compound of the formula (II) with a heterocyclic carbamate of the formula (III) R*—O—CO—NR4—A (III) in which R* is optionally substituted phenyl or (C1-C4)alkyl, or b) reacting a pyridylsulfonylcarbamate of the formula (IV) with an amino heterocycle of the formula (V) H—NR4—A (V) orc) reacting a sulfonyl isocyanate of the formula (VI) with an amino heterocycle of the formula (V) H—NR4—A (V) ord) reacting, in a one-pot reaction, first an amino heterocycle of the formula H—NR4—A (V) with phosgene in the presence of a base and reacting the intermediate formed with a pyridine-sulfonamide of the formula (II), where, in formulae (II)-(VI), R1, R2, R3, R4, A, m and n are as defined in formula I.
- 46. A process for the preparation of a compound of formula (II) in which R1, R2, R3, m and n are as defined in claim 1, which comprises reacting a compound of the formula (VII) in which R2, m and n are as defined in formula (II), with carboxylic acid halides of the formula Hal—CO—R2 (Hal=halogen) or symmetric or mixed carboxylic anhydrides of the formula R2—CO—O—CO—R+ in which R+ is defined analogously to R2 or is another aliphatic or aromatic radical, and subsequently reacting the resulting 3-(N-acylamino)-pyridine2-sulfamide which is protected with the t-butyl groupa) with a strong acid to give the free 3-(N-acylamino)pyridine-2-sulfamide of the formula (II) in which R1=H, or b) reducing it to the N-alkyl compound, N-acylating the N-alkyl compound with a compound of the formula Hal—CO—R2 or R2—CO—O—CO—R+ and eliminating the t-butyl protective group with a strong acid, giving the free 3-(N-acylamino)pyridine-2-sulfamide of the formula (II) in which R1 is other than hydrogen.
Priority Claims (1)
Number |
Date |
Country |
Kind |
42 04 411 |
Feb 1992 |
DE |
|
Parent Case Info
This application is a continuation of application Ser. No. 08/016,758, filed Feb. 11, 1993.
US Referenced Citations (6)
Foreign Referenced Citations (12)
Number |
Date |
Country |
7804691 |
Dec 1991 |
AU |
0013480 |
Jul 1980 |
EP |
0084224 |
Jul 1983 |
EP |
0103543 |
Mar 1984 |
EP |
0125864 |
Nov 1984 |
EP |
0237292 |
Sep 1987 |
EP |
0272855 |
Jun 1988 |
EP |
0451468 |
Oct 1991 |
EP |
0459949 |
Dec 1991 |
EP |
WO 8804297 |
Jun 1988 |
WO |
WO 9110660 |
Jul 1991 |
WO |
910173 |
Jan 1991 |
ZA |
Non-Patent Literature Citations (4)
Entry |
Chemical Abstracts 108: 21919v, Kimura et al, Abstract of EP 232067, Published Aug. 1987.* |
CA 108: 21919v by Kimura et al. Abstract of EP232067 Published Aug. 1987.* |
Chemical Abstracts 108: 21919v by Kimura et al, Abstract of EP 232067, Published Aug. 1987.* |
Chemical Abstract, vol. 118, No. 15, Apr. 12, 1992, p. 844. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
08/016758 |
Feb 1993 |
US |
Child |
08/333882 |
|
US |