Acylsulfamoylbenzamides, crop protection compositions comprising them, and processes for their preparation

An acylsulfamoylbenzarnide compound having the formula I:

• or, its salt,
• in which
• X is CH or N;
• R1 is hydrogen, heterocyclyl or a hydrocarbon radical, where the two last mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 and Za—Ra;
• R2 is hydrogen, hydroxyl, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, where the five last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio, or R1 and R2 together with the linking nitrogen atom form a 3- to 8-membered saturated or unsaturated ring;
• R3 is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 or Zb—Rb;
• R4 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl;
• R5 is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH2, SO2NH2 or Zc—Rc;
• Ra is a (C2-C20)-alkyl radical whose hydrocarbon chain is interrupted once or more than once by oxygen atoms, is heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-((C1-C4)-alkyl)amino;
• Rb, Rc independently of one another are a (C2-C20)-alkyl radical whose hydrocarbon chain is interrupted once or more than once by oxygen atoms, are heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, anino, hydroxyl, phosphoryl, (C1-C4)-haloalkoxy, mono- and di-((C1-C4)-alkyl)amino;
• Za is a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NRd or SO2NRd;
• Zb, Zc independently of one another are a direct bond or a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NRd, SO2NRd or C(O)NRd;
• Rd is hydrogen, (C1-C4)-alkyl or (C1-C4)-haloalkyl;
• n is an integer from 0 to 4 and
• m, in the case that X is CH, is an integer from 0 to 5, and, in the case that X is N, is an integer from 0 to 4;
• with the proviso that R5 is not attached directly adjacent to X if X is N and that R1 is not phenyl, benzyl or 4-carboxyphenyl if X is CH and R2, R4 and R5 are each hydrogen.