HETEROCYCLIC ACETYLENE COMPOUNDS

摘要

Heterocyclic acetylene compounds The novel compounds of the formula I Z - C ? C - Het - Y - Q - A (I) are useful selective herbicides for post-emergence application in crops of cereals, rice and maize. The symbols in the formula I have the following meanings: Het is a 5-6-membered heterocyclic radical which is unsubstituted or substituted by one to three radicals R, and which contains as ring members 1 to 3 hetero atoms from the group comprising nitrogen, oxygen and sulfur, oxygen and sulfur being present at most once per heterocyclic radical, A is a group -NR1R2 or -N?HR1R2X?, R1 and R2 independently of one another are each hydrogen, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, or C1-C6-alkyl which is unsubstituted or substituted by halogen, hydroxyl, C1-C4-alkoxy, alkoxycarbonyl having at most 5 carbon atoms, cyano or carboxyl, or R1 and R2 together with the nitrogen atom carrying them form a 5- or 6-membered, saturated heterocyclic radical having in all at most 2 hetero atoms, which radical can be substituted by C1-C3-alkyl, X? is an anion, Y is oxygen, sulfur or a radical -NR3-, R3 is hydrogen, C3-C6-alkenyl, C3-C6-alkynyl or C3-C8- cycloalkyl, or C1-C6-alkyl which is unsubstituted or substituted by hydroxyl, C1-C4-alkoxy, alkoxycarbonyl having at most 5 carbon atoms, cyano or carboxyl, Q is a straight-chain or branched-chain C2-C6-alkylene bridge, R is hydrogen, nitro, cyano, trifluoromethyl, C1-C4- alkoxy, C1-C4-alkylthio, -NR4R5, -CO-NR6R7, -COOR8, -CO-SR9, halogen or -N3, or C1-C4-alkyl which is unsubstituted or substituted by C1-C4-alkoxy, hydroxyl, cyano or -COOR8, R4, R6, R7, R8 and R9 independently of one another are each hydrogen or C1-C6-alkyl, C3-C8-alkenyl or C3-C8-alkynyl, R5 is hydrogen, C1-C6-alkyl, C3-C8-alkenyl, C3-C8- alkynyl, -CO-R10, -COO-R11 or -CO-NHR12, and R10, R11 and R12 have the same meanings as R3, and Z is a phenyl, naphthyl or heterocyclic, aromatic group which contains at least one oxygen, sulfur or nitrogen atom, and which is unsubstituted or is substituted by one to three radicals which have the same meaning as that given for R, or are formyl, -SO2NR6R7, -NH-NH2, -NHOH, -SO-R8, -SO2-R8, -N=CH-NR6R7 or COO?M? , or C2-C6-alkenyl which is unsubstituted or substituted by nitro, cyano or -COOR8, M? being a sodium, potassium, calcium or magnesium cation.