2-(HET)ARYL-SUBSTITUTED CONDENSED HETEROCYCLE DERIVATIVES AS PEST CONTROL AGENTS

Abstract

The invention relates to novel compounds of the formula (I)

##STR00001## in which A.sup.1, A.sup.3, X, R.sup.1, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8 and n have the definitions given above, to the use thereof as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for preparation thereof.

Claims

1. A compound of formula (I) ##STR00037## in which A.sup.1 is nitrogen, =N.sup.+(O.sup.?) or =C(H), A.sup.3 is nitrogen, =N.sup.+(O.sup.?) or =C(H), X is oxygen or sulfur, R.sup.1 is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)haloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfinyl-(C.sub.1-C.sub.6)alkyl or (C.sub.1-C.sub.6)alkylsulfonyl-(C.sub.1-C.sub.6)alkyl, R.sup.3 is hydrogen, cyano, halogen, nitro, hydroxyl, amino, SCN, tri-(C.sub.1-C.sub.6)alkylsilyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, cyano(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino, aminosulfonyl, (C.sub.1-C.sub.6)alkylaminosulfonyl, di(C.sub.1-C.sub.6)alkylaminosulfonyl, (C.sub.1-C.sub.6)alkylsulfoximino, (C.sub.3-C.sub.8)cycloalkylamino or NHCO(C.sub.1-C.sub.6)alkyl ((C.sub.1-C.sub.6)alkylcarbonylamino), R.sup.4 is hydrogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)cyanoalkyl, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)cyanoalkenyl, (C.sub.2-C.sub.4)alkynyl, (C.sub.2-C.sub.4)haloalkynyl, (C.sub.2-C.sub.4)cyanoalkynyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl or (C.sub.1-C.sub.4)haloalkylsulfonyl, R.sup.6 is hydrogen, cyano, halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)alkylaminosulfonyl or di(C.sub.1-C.sub.6)alkylaminosulfonyl, R.sup.7, R.sup.8 are independently hydrogen, cyano, halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, cyano(C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)alkylaminosulfonyl or di(C.sub.1-C.sub.6)alkylaminosulfonyl, n is 0, 1 or 2.

2. The compound of formula (I) according to claim 1, in which A.sup.1 is nitrogen, =N.sup.+(O.sup.?) or =C(H), A.sup.3 is nitrogen, =N.sup.+(O.sup.?) or =C(H), X is oxygen or sulfur, R.sup.1 is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)haloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl or (C.sub.1-C.sub.6)haloalkoxy-(C.sub.1-C.sub.6)alkyl, R.sup.3 is hydrogen, cyano, halogen, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, cyano(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkylhydroxyimino, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)alkylaminosulfonyl, di(C.sub.1-C.sub.6)alkylaminosulfonyl, (C.sub.1-C.sub.6)alkylsulfoximino or NHCO(C.sub.1-C.sub.6)alkyl ((C.sub.1-C.sub.6)alkylcarbonylamino), R.sup.4 is hydrogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)haloalkenyl, (C.sub.2-C.sub.4)alkynyl, (C.sub.2-C.sub.4)haloalkynyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl or (C.sub.1-C.sub.4)haloalkylsulfonyl, R.sup.6 is hydrogen, cyano, halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkylcarbonyl or (C.sub.1-C.sub.6)haloalkylcarbonyl, R.sup.7, R.sup.8 are independently hydrogen, cyano, halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.8)cycloalkyl, halo(C.sub.3-C.sub.5)cycloalkyl, cyano(C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl or (C.sub.1-C.sub.6)haloalkylsulfonyl, n is 0, 1 or 2.

3. The compound of formula (I) according to claim 1, in which A.sup.1 is nitrogen, =N.sup.+(O.sup.?) or =C(H), A.sup.3 is nitrogen, =N.sup.+(O.sup.?) or =C(H), X is oxygen or sulfur, R.sup.1 is (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl or (C.sub.3-C.sub.6)cycloalkyl, R.sup.3 is hydrogen, cyano, halogen, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, cyano(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl or (C.sub.1-C.sub.6)alkylsulfoximino, R.sup.4 is hydrogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4), alkoxy-(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)haloalkyl, R.sup.6 is hydrogen, cyano, halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkylcarbonyl or (C.sub.1-C.sub.6)haloalkylcarbonyl, R.sup.7, R.sup.8 are independently hydrogen, cyano, halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, cyano(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.4)alkoxyimino, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl or (C.sub.1-C.sub.4)haloalkylsulfonyl, n is 0, 1 or 2.

4. The compound of formula (I) according to claim 1, in which A.sup.1 is nitrogen, A.sup.3 is nitrogen or =C(H), X is oxygen, R.sup.1 is (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl or (C.sub.3-C.sub.4)cycloalkyl, R.sup.3 is hydrogen, cyano, halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl or (C.sub.1-C.sub.4)alkoxyimino, R.sup.4 is hydrogen or (C.sub.1-C.sub.4)alkyl, R.sup.6 is hydrogen, R.sup.7 is cyano, halogen, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.3-C.sub.4)cycloalkyl, cyano(C.sub.3-C.sub.4)cycloalkyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkoxycarbonyl, (C.sub.1-C.sub.4)alkoxyimino, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)haloalkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl or (C.sub.1-C.sub.4)haloalkylsulfonyl, R.sup.8 is hydrogen or cyano, n is 0, 1 or 2.

5. The compound of formula (I) according to claim 1, in which A.sup.1 is nitrogen, A.sup.3 is nitrogen or =C(H), X is oxygen, R.sup.1 is methyl, ethyl, n-propyl or i-propyl, R.sup.3 is hydrogen, R.sup.4 is methyl, R.sup.6 is hydrogen, R.sup.7 is cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, methoxycarbonyl, methoxyimino or cyanocyclopropyl, R.sup.8 is hydrogen or chlorine, n is 0, 1 or 2.

6. The compound of formula (I) according to claim 1, in which A.sup.1 is nitrogen, A.sup.3 is nitrogen or =C(H), X is oxygen, R.sup.1 is ethyl, R.sup.3 is hydrogen, R.sup.4 is methyl, R.sup.6 is hydrogen, R.sup.7 is cyano, fluorine, chlorine, bromine, iodine, methoxycarbonyl (COOCH.sub.3), methoxyimino (CH?NOCH.sub.3) or 1-cyano-1-cyclopropyl, R.sup.8 is hydrogen or chlorine, n is 2.

7. The compound of formula (I) according to claim 1, in which A.sup.3 is nitrogen and A.sup.1, X, R.sup.1, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8 and n have the definitions given in claim 1, 2, 3, 4, 5 or 6.

8. The compound of formula (I) according to claim 1, in which A.sup.3 is =C(H) and A.sup.1, X, R.sup.1, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8 and n have the definitions given in claim 1, 2, 3, 4, 5 or 6.

9. The compound of formula (I) according to claim 1, in which the compounds have the following structure: ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042##

10. An Agrochemical formulation comprising a compound of formula (I) according to claim 1, and one or more extenders and/or surfactants.

11. The Agrochemical formulation according to claim 10, additionally comprising a further active agrochemical ingredient.

12. A method of controlling animal pests, comprising allowing a compound according to claim 1 to act on one or more animal pests and/or a habitat thereof.

13. A compound according to claim 1 or an agrochemical formulation thereof for controlling one or more animal pests.

Description

Preparation Examples

Example I-02

2-[5-Ethylsulfonyl-6-[3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridin-2-yl]-2-pyridyl]-4-(4-fluorophenyl)-1,2,4-triazol-3-one

[0477] ##STR00005##

[0478] 59 mg (0.13 mmol) of 2-(3-ethylsulfonyl-6-fluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine was dissolved in 6 ml of acetonitrile, 66.4 mg (0.20 mmol) of caesium carbonate, 11.4 mg (0.06 mmol) of potassium iodide and 38.1 mg (0.20 mmol) of 4-(4-fluorophenyl)-1H-1,2,4-triazol-5-one were added, and the mixture was stirred at room temperature for 20 h. Subsequently, the reaction mixture was filtered, and the filtrate was freed of the solvent under reduced pressure.

[0479] The residue was dissolved in 2 ml of dichloromethane and purified by column chromatography purification with a cyclohexane/ethyl acetate solvent mixture (2:1) as eluent.

[0480] log P (neutral): 3.53; MH.sup.+: 598; .sup.1H-NMR (400 MHz, D6-DMSO) ? ppm: 1.25 (t, 3H), 3.88 (q, 2H), 3.91 (s, 3H), 7.42-7.46 (m, 2H), 7.75-7.79 (m, 2H), 8.50 (d, 1H), 8.67-8.72 (m, 2H), 8.81 (s, 1H), 8.85-8.86 (m, 1H).

2-(3-Ethylsulfonyl-6-fluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine

[0481] ##STR00006##

[0482] 2.20 g (5.41 mmol) of 2-(3-ethylsulfanyl-6-fluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine was dissolved in 120 ml of dichloromethane, 2.44 g (53.0 mmol) of formic acid and 4.87 g (50.0 mmol) of 35% hydrogen peroxide were added at room temperature, and then the mixture was stirred at room temperature for 17 h. The mixture was diluted with 20 ml of water, 3 ml of sodium bisulfite solution was added, the mixture was stirred for 30 min, and then saturated sodium carbonate solution was added. The organic phase was separated off, the aqueous phase was extracted twice with dichloromethane, and then the combined organic phases were freed of the solvent under reduced pressure. The residue was used in the next stage without further purification.

[0483] log P (neutral): 3.33; MH.sup.+: 439; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) ? ppm: 1.22 (t, 3H), 3.79-3.85 (m, 5H), 7.79-7.82 (m, 1H), 8.67 (d, 1H), 8.70-8.74 (m, 1H), 8.85 (d, 1H).

2-(3-Ethylsulfanyl-6-fluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine

[0484] ##STR00007##

[0485] 2.54 g (6.97 mmol) of 2-(3,6-difluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine was dissolved in 32 ml of tetrahydrofuran, the mixture was cooled to ?10? C., and 285 mg (7.11 mmol) of sodium hydride was added. Stirring was continued at ?10 to ?15? C. for a further 15 min, and then 477 mg (7.67 mmol) of ethanethiol, dissolved in 5 ml of tetrahydrofuran, was added dropwise over the course of 50 minutes. The mixture was stirred at ?10 to ?5? C. for a further 3 h and then poured onto ice-water, and the precipitated solids were filtered off. The residue was purified by column chromatography purification by means of preparative HPLC with a water/acetonitrile gradient as eluent.

[0486] log P (acidic): 4.05; MH.sup.+: 407; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) ? ppm: 1.20 (t, 3H), 3.03 (q, 2H), 3.96 (s, 3H), 7.48-7.51 (m, 1H), 8.27-8.31 (m, 1H), 8.63 (d, 1H), 8.81 (d, 1H).

2-(3,6-Difluoro-2-pyridyl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-b]pyridine

[0487] ##STR00008##

[0488] 3.50 g (13.7 mmol) of N2-methyl-5-(1,1,2,2,2-pentafluoroethyl)pyridine-2,3-diamine, 2.83 g (17.2 mmol) of 3,6-difluoropyridine-2-carboxylic acid and 4.01 g (20.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) were stirred in 60 ml of pyridine at room temperature for 16 h. The reaction mixture was freed of the solvent under reduced pressure, and the residue was taken up in 80 ml of glacial acetic acid and stirred under reflux for 6 h. Subsequently, the solvent was distilled off under reduced pressure and the residue was partitioned between dichloromethane and a semisaturated sodium hydrogencarbonate solution.

[0489] The organic phase was removed, dried over sodium sulfate and concentrated. The residue was admixed with 10 ml of methyl tert-butyl ether and stirred. The remaining residue was finally filtered off and dried.

[0490] log P (neutral): 3.30; MH.sup.+: 365; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) ? ppm: 4.07 (s, 3H), 7.59-7.63 (m, 1H), 8.27-8.33 (m, 1H), 8.67 (d, 1H), 8.82 (d, 1H).

[0491] In analogy to the examples and according to the above-described preparation processes, the following compounds of the formula (I) can be obtained:

TABLE-US-00001 Ex. Structure I-01 [00009] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8988 (8.3); 8.8587 (7.0); 8.8330 (0.8); 8.7547 (3.1); 8.7325 (4.2); 8.5943 (4.2); 8.5720 (3.6); 8.4617 (0.4); 8.3684 (0.4); 8.3158 (1.4); 7.7009 (1.1); 7.6986 (1.0); 7.6810 (2.0); 7.6787 (1.7); 7.6706 (2.1); 7.6663 (3.0); 7.6617 (1.4); 7.6204 (1.5); 7.6005 (2.6); 7.5807 (1.3); 7.5547 (0.4); 7.4552 (1.6); 7.4355 (1.2); 4.0645 (16.0); 3.9906 (1.9); 3.8248 (0.9); 3.8065 (3.2); 3.7881 (3.2); 3.7698 (0.9); 3.6532 (0.4); 3.6340 (0.4); 3.3303 (680.0); 2.6758 (2.6); 2.6713 (3.5); 2.6667 (2.5); 2.6623 (1.2); 2.5947 (0.3); 2.5247 (12.4); 2.5199 (19.3); 2.5113 (215.9); 2.5069 (423.1); 2.5023 (543.5); 2.4977 (391.0); 2.4933 (189.0); 2.3382 (1.2); 2.3337 (2.5); 2.3291 (3.3); 2.3246 (2.4); 2.3202 (1.2); 1.8526 (1.1); 1.8400 (3.7); 1.8328 (3.8); 1.8213 (1.5); 1.7563 (0.5); 1.7499 (0.4); 1.6264 (1.5); 1.6138 (3.6); 1.6067 (3.8); 1.5933 (1.1); 1.4683 (0.4); 1.4619 (0.4); 1.2781 (0.5); 1.2622 (3.5); 1.2437 (8.2); 1.2252 (3.5); 1.2170 (0.7); 1.1981 (1.0); 1.1800 (0.4); 0.1460 (1.2); 0.0079 (10.8); ?0.0002 (300.2); ?0.0085 (10.7); ?0.1496 (1.2) I-02 [00010] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8553 (2.2); 8.8505 (2.2); 8.8188 (8.5); 8.7196 (3.2); 8.6975 (4.1); 8.6783 (2.3); 8.6735 (2.2); 8.5145 (4.1); 8.4924 (3.6); 7.7876 (2.1); 7.7819 (0.8); 7.7755 (2.3); 7.7702 (1.3); 7.7648 (2.6); 7.7584 (0.8); 7.7527 (2.4); 7.4612 (2.5); 7.4555 (0.7); 7.4486 (0.3); 7.4440 (0.9); 7.4392 (3.9); 7.4342 (0.8); 7.4227 (0.7); 7.4170 (2.2); 3.9085 (16.0); 3.8912 (3.0); 3.8727 (2.9); 3.8543 (0.8); 3.3285 (141.7); 2.8913 (0.7); 2.7326 (0.6); 2.6762 (0.5); 2.6716 (0.7); 2.6671 (0.5); 2.5252 (2.2); 2.5205 (3.2); 2.5118 (43.7); 2.5073 (89.0); 2.5027 (115.5); 2.4981 (80.7); 2.4935 (37.4); 2.3341 (0.5); 2.3295 (0.7); 2.3250 (0.5); 2.0864 (1.8); 1.2660 (3.2); 1.2475 (7.6); 1.2290 (3.2); 1.0692 (0.5); 0.0080 (0.5); ?0.0002 (16.5); ?0.0085 (0.5) I-03 [00011] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9956 (7.5); 8.8573 (2.5); 8.8528 (2.6); 8.7293 (2.9); 8.7071 (3.7); 8.6814 (2.7); 8.6769 (2.6); 8.5158 (3.7); 8.4937 (3.2); 8.1555 (3.9); 8.1511 (1.4); 8.1384 (1.6); 8.1337 (5.1); 7.9695 (4.9); 7.9650 (1.6); 7.9477 (4.1); 4.3690 (0.6); 4.3564 (1.3); 4.3437 (0.7); 3.9140 (16.0); 3.8920 (15.0); 3.8778 (3.4); 3.8593 (1.0); 3.4741 (0.3); 3.4613 (0.4); 3.4566 (1.1); 3.4439 (1.1); 3.4392 (1.1); 3.4265 (1.1); 3.4217 (0.4); 3.4090 (0.4); 3.3339 (48.4); 2.6725 (0.4); 2.5259 (1.3); 2.5120 (24.9); 2.5082 (48.4); 2.5037 (62.2); 2.4992 (45.3); 2.4950 (22.6); 2.3305 (0.4); 1.2687 (3.4); 1.2503 (7.7); 1.2317 (3.4); 1.0741 (2.4); 1.0567 (4.7); 1.0392 (2.3); 0.0078 (1.5); ?0.0002 (41.7); ?0.0085 (1.6) I-04 [00012] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8884 (7.6); 8.8566 (2.4); 8.8521 (2.5); 8.7187 (3.0); 8.6966 (3.9); 8.6804 (2.5); 8.6757 (2.4); 8.5331 (3.8); 8.5109 (3.3); 8.3157 (3.1); 7.7016 (0.9); 7.6991 (1.0); 7.6968 (1.0); 7.6791 (1.8); 7.6769 (1.6); 7.6643 (1.9); 7.6598 (2.9); 7.6554 (1.5); 7.6167 (1.4); 7.5971 (2.6); 7.5772 (1.3); 7.4557 (1.5); 7.4360 (1.2); 7.4318 (1.0); 3.9018 (16.0); 3.8842 (3.1); 3.8657 (3.1); 3.8472 (0.9); 3.3247 (92.8); 3.3009 (1.7); 2.6757 (0.7); 2.6711 (0.9); 2.6667 (0.6); 2.5245 (3.2); 2.5111 (53.9); 2.5067 (106.6); 2.5022 (138.3); 2.4977 (98.9); 2.4932 (47.7); 2.3335 (0.6); 2.3290 (0.8); 2.3245 (0.6); 1.8501 (1.2); 1.8373 (3.6); 1.8302 (3.7); 1.8186 (1.5); 1.6255 (1.5); 1.6131 (3.6); 1.6061 (3.7); 1.5926 (1.2); 1.2647 (3.4); 1.2463 (7.7); 1.2277 (3.3); 0.1459 (0.4); 0.0079 (3.4); ?0.0002 (84.9); ?0.0085 (3.1); ?0.1497 (0.4) I-05 [00013] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 9.0607 (7.1); 8.8688 (5.7); 8.7768 (3.3); 8.7546 (4.1); 8.5527 (3.8); 8.5305 (3.5); 8.3192 (0.4); 8.2703 (3.5); 8.2652 (3.6); 8.2446 (2.8); 8.2232 (3.5); 8.0678 (2.2); 8.0627 (2.0); 8.0464 (1.8); 8.0411 (1.7); 4.0682 (16.0); 3.8338 (0.9); 3.8153 (3.2); 3.7968 (3.2); 3.7783 (0.9); 3.3354 (122.5); 2.6764 (1.1); 2.6719 (1.4); 2.6674 (1.1); 2.5253 (4.6); 2.5117 (87.9); 2.5074 (172.1); 2.5028 (226.8); 2.4983 (172.0); 2.4940 (86.8); 2.3342 (1.0); 2.3298 (1.4); 2.3252 (1.0); 2.0765 (0.4); 1.2627 (3.6); 1.2442 (8.1); 1.2257 (3.5); ?0.0002 (1.0) I-06 [00014] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 9.0145 (7.9); 8.8606 (6.6); 8.7703 (3.2); 8.7481 (4.0); 8.5668 (4.0); 8.5445 (3.6); 8.1055 (3.1); 8.1005 (1.3); 8.0885 (1.8); 8.0833 (5.9); 8.0337 (5.8); 8.0285 (1.7); 8.0165 (1.3); 8.0114 (3.2); 4.0726 (16.0); 3.8352 (0.9); 3.8167 (3.1); 3.7982 (3.2); 3.7797 (0.9); 3.3282 (74.2); 2.6763 (0.4); 2.6718 (0.6); 2.6672 (0.4); 2.5252 (1.8); 2.5117 (38.9); 2.5074 (77.6); 2.5028 (100.3); 2.4983 (72.0); 2.4938 (34.6); 2.3342 (0.4); 2.3297 (0.6); 2.3251 (0.4); 1.2646 (3.5); 1.2462 (8.1); 1.2277 (3.5); 0.0080 (1.1); ?0.0002 (30.0); ?0.0085 (1.1) I-07 [00015] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9371 (7.2); 8.8587 (2.7); 8.8544 (2.9); 8.7361 (3.1); 8.7140 (3.8); 8.6813 (2.9); 8.6770 (2.8); 8.4906 (3.7); 8.4685 (3.3); 8.4070 (3.3); 8.4005 (3.5); 8.2015 (1.6); 8.1950 (1.5); 8.1793 (2.0); 8.1727 (2.0); 8.0068 (3.4); 7.9846 (2.8); 3.9073 (16.0); 3.8939 (3.5); 3.8754 (3.3); 3.8569 (1.0); 3.3282 (38.8); 2.6721 (0.4); 2.5075 (50.6); 2.5031 (65.2); 2.4987 (49.0); 2.3299 (0.4); 1.2668 (3.6); 1.2484 (7.9); 1.2299 (3.5); 0.0078 (0.6); ?0.0002 (12.2); ?0.0082 (0.6) I-08 [00016] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9465 (6.8); 8.8620 (6.2); 8.7732 (3.0); 8.7510 (3.8); 8.5558 (3.6); 8.5336 (3.1); 8.4108 (3.3); 8.4042 (3.4); 8.3161 (0.7); 8.2600 (0.4); 8.2051 (1.8); 8.1984 (1.6); 8.1828 (2.1); 8.1764 (2.0); 8.0145 (3.4); 7.9923 (2.8); 4.0690 (16.0); 4.0378 (1.8); 3.8950 (0.8); 3.8323 (1.0); 3.8142 (3.2); 3.7956 (3.3); 3.7774 (1.0); 3.3265 (223.7); 2.6755 (2.2); 2.6713 (2.9); 2.6667 (2.1); 2.5708 (0.3); 2.5244 (8.7); 2.5066 (382.2); 2.5022 (478.0); 2.4978 (342.6); 2.3335 (2.1); 2.3291 (2.8); 2.3247 (2.0); 2.0747 (1.4); 1.2637 (3.7); 1.2453 (8.3); 1.2268 (3.6); ?0.0001 (1.8) I-09 [00017] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8734 (7.3); 8.8570 (6.5); 8.7536 (2.9); 8.7314 (3.8); 8.5679 (3.7); 8.5457 (3.1); 8.3163 (0.4); 7.9570 (4.4); 7.9353 (5.1); 7.8229 (0.8); 7.8148 (0.8); 7.8080 (0.7); 7.7957 (0.9); 7.7913 (0.8); 7.7829 (1.0); 7.5835 (5.1); 7.5617 (4.6); 7.4781 (1.0); 7.4653 (1.6); 7.4610 (1.6); 7.3847 (1.1); 7.3705 (0.4); 7.3445 (1.0); 4.0656 (16.0); 3.8281 (1.0); 3.8099 (3.4); 3.7914 (3.4); 3.7730 (1.1); 3.3261 (160.5); 2.6755 (1.2); 2.6713 (1.6); 2.6670 (1.2); 2.5067 (197.4); 2.5023 (252.7); 2.4981 (189.7); 2.3334 (1.2); 2.3291 (1.6); 2.3247 (1.2); 1.2609 (3.8); 1.2425 (8.3); 1.2240 (3.7); 0.1458 (0.6); 0.0079 (6.6); ?0.0001 (122.0); ?0.0078 (5.8); ?0.1495 (0.6) I-10 [00018] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8583 (7.2); 8.8298 (8.2); 8.7562 (3.1); 8.7340 (4.0); 8.5770 (4.1); 8.5665 (0.3); 8.5548 (3.5); 7.7901 (2.3); 7.7847 (1.0); 7.7780 (2.5); 7.7728 (1.5); 7.7675 (2.8); 7.7608 (1.0); 7.7554 (2.6); 7.4663 (2.7); 7.4607 (0.9); 7.4442 (4.4); 7.4276 (0.8); 7.4221 (2.4); 5.7565 (0.6); 4.0703 (16.0); 4.0522 (0.6); 3.8310 (1.0); 3.8126 (3.4); 3.7941 (3.4); 3.7757 (1.0); 3.3264 (123.2); 2.6758 (0.7); 2.6713 (0.9); 2.6667 (0.7); 2.5246 (3.2); 2.5112 (57.6); 2.5069 (112.0); 2.5024 (145.3); 2.4978 (106.6); 2.4935 (52.6); 2.3336 (0.7); 2.3292 (0.9); 2.3246 (0.7); 2.0864 (0.4); 1.2630 (3.7); 1.2445 (8.2); 1.2260 (3.7); 1.2110 (0.4); 1.1402 (0.4); 0.0076 (1.6); ?0.0002 (39.5); ?0.0083 (1.5) I-11 [00019] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9183 (8.2); 8.8590 (7.5); 8.7612 (3.1); 8.7390 (4.0); 8.5699 (4.0); 8.5477 (3.5); 8.0378 (1.9); 8.0330 (3.5); 8.0282 (2.0); 7.8110 (1.5); 7.8081 (1.4); 7.7907 (1.7); 7.7880 (1.6); 7.6749 (1.3); 7.6727 (1.2); 7.6705 (1.1); 7.6547 (1.7); 7.6525 (1.8); 7.5672 (2.1); 7.5470 (3.2); 7.5267 (1.4); 7.4642 (0.5); 7.4598 (0.5); 7.4203 (0.3); 7.4151 (0.3); 7.3837 (0.4); 7.3433 (0.4); 7.3393 (0.4); 5.7569 (3.8); 4.0707 (16.0); 3.8310 (1.0); 3.8126 (3.4); 3.7941 (3.4); 3.7756 (1.0); 3.3262 (33.2); 2.6720 (0.4); 2.5252 (1.4); 2.5075 (52.6); 2.5030 (68.5); 2.4985 (51.1); 2.4943 (26.1); 2.3343 (0.3); 2.3297 (0.4); 1.2642 (3.7); 1.2458 (8.2); 1.2273 (3.6); 0.0078 (0.6); ?0.0002 (16.2); ?0.0084 (0.7) I-12 [00020] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9245 (8.0); 8.8592 (6.8); 8.7628 (3.2); 8.7406 (4.2); 8.5758 (4.1); 8.5536 (3.6); 7.7252 (1.0); 7.7220 (1.2); 7.7172 (0.9); 7.6963 (1.3); 7.6908 (0.9); 7.6673 (0.5); 7.6627 (0.4); 7.6552 (1.9); 7.6520 (2.2); 7.6470 (2.5); 7.6432 (2.6); 7.6247 (1.2); 7.6045 (0.4); 7.4643 (0.4); 7.4600 (0.4); 7.3842 (0.4); 7.3432 (0.8); 7.3356 (0.8); 7.3275 (0.8); 7.3208 (0.9); 7.3172 (0.8); 7.3147 (0.8); 7.3105 (0.6); 7.3023 (0.5); 7.2979 (0.6); 7.2919 (0.4); 4.0722 (16.0); 3.8329 (0.9); 3.8145 (3.3); 3.7960 (3.3); 3.7775 (1.0); 3.3276 (35.7); 2.6763 (0.3); 2.6717 (0.5); 2.6674 (0.4); 2.5253 (1.4); 2.5205 (2.2); 2.5118 (27.6); 2.5074 (56.9); 2.5029 (76.3); 2.4983 (57.2); 2.4939 (29.0); 2.3342 (0.3); 2.3296 (0.5); 2.3250 (0.4); 2.0753 (4.4); 1.2646 (3.6); 1.2462 (8.1); 1.2277 (3.5); 0.0079 (0.7); ?0.0002 (22.8); ?0.0085 (0.9) I-13 [00021] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9236 (6.9); 8.8600 (6.2); 8.7623 (3.0); 8.7401 (3.8); 8.5723 (3.7); 8.5501 (3.1); 8.3158 (0.5); 7.9147 (1.9); 7.9099 (3.4); 7.9051 (1.9); 7.7762 (1.4); 7.7582 (1.7); 7.7559 (1.7); 7.7534 (1.7); 7.6383 (1.5); 7.6181 (3.1); 7.5979 (1.8); 7.5463 (1.8); 7.5441 (1.9); 7.5417 (1.8); 7.5261 (1.2); 7.5239 (1.2); 7.5214 (1.2); 5.7560 (0.7); 4.0706 (16.0); 3.8310 (1.0); 3.8125 (3.4); 3.7940 (3.4); 3.7757 (1.0); 3.3236 (83.4); 2.6752 (1.5); 2.6709 (2.0); 2.6667 (1.5); 2.5063 (249.0); 2.5019 (312.7); 2.4976 (230.1); 2.3331 (1.5); 2.3289 (1.9); 2.3244 (1.4); 1.2638 (3.9); 1.2453 (8.8); 1.2347 (2.2); 1.2270 (4.1); 0.1462 (0.4); 0.0076 (4.1); ?0.0003 (88.5); ?0.0084 (3.7); ?0.1496 (0.4) I-14 [00022] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8833 (8.2); 8.8574 (7.3); 8.7573 (3.2); 8.7351 (4.2); 8.5703 (4.1); 8.5481 (3.6); 7.8091 (3.6); 7.8038 (1.5); 7.7923 (1.8); 7.7868 (6.6); 7.7804 (1.0); 7.7421 (0.8); 7.7355 (6.3); 7.7301 (1.7); 7.7186 (1.3); 7.7132 (3.6); 7.4646 (0.4); 7.4600 (0.4); 7.3841 (0.4); 4.0692 (16.0); 3.8312 (0.9); 3.8127 (3.3); 3.7942 (3.3); 3.7758 (1.0); 3.3264 (42.3); 2.6762 (0.3); 2.6718 (0.5); 2.6675 (0.4); 2.5252 (1.2); 2.5204 (1.9); 2.5117 (27.6); 2.5073 (56.5); 2.5028 (75.2); 2.4982 (55.8); 2.4938 (27.9); 2.3342 (0.3); 2.3297 (0.5); 2.3249 (0.3); 1.2628 (3.6); 1.2444 (8.2); 1.2259 (3.5); 0.0080 (1.0); ?0.0002 (32.8); ?0.0084 (1.2) I-15 [00023] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 20.0119 (0.5); 19.2639 (0.7); 18.5128 (1.5); 16.0399 (0.4); 15.5098 (1.0); 12.5016 (0.5); 9.5488 (0.4); 9.5016 (7.0); 9.5001 (2.8); 9.4964 (0.8); 9.4936 (0.7); 9.4919 (0.7); 9.4787 (0.8); 9.4126 (0.4); 9.4083 (0.4); 9.1768 (0.4); 8.1011 (0.4); 8.0959 (0.5); 8.0943 (0.6); 8.0907 (0.4); 8.0591 (0.4); 8.0384 (0.5); 8.0323 (0.6); 8.0295 (0.4); 8.0237 (1.4); 8.0156 (1.2); 8.0149 (0.9); 8.0119 (1.4); 8.0111 (0.9); 8.0105 (1.6); 8.0097 (2.0); 8.0089 (2.4); 8.0068 (2.2); 8.0060 (3.2); 8.0053 (2.5); 8.0047 (2.0); 8.0038 (3.3); 8.0030 (3.2); 8.0024 (4.7); 8.0017 (7.3); 8.0009 (16.0); 8.0002 (15.9); 7.9727 (0.5); 7.9565 (0.5); 7.9551 (0.5); 7.9533 (0.5); 7.8645 (0.4); 7.7889 (0.5); 7.6530 (0.4); 7.0872 (0.4); 6.4945 (2.1); 6.4914 (0.8); 6.4898 (0.8); 6.4866 (0.9); 6.4808 (0.4); 6.4745 (0.7); 3.4944 (3.3); 3.3295 (1.2); 2.5115 (0.8); 2.5070 (1.1); 0.4998 (0.4); 0.4915 (1.3); 0.0046 (0.7); ?0.0400 (0.4); ?1.7615 (0.4) I-16 [00024] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9132 (7.8); 8.8599 (2.4); 8.8555 (2.5); 8.7265 (3.0); 8.7043 (3.8); 8.6855 (2.6); 8.6809 (2.5); 8.5129 (3.8); 8.4908 (3.4); 7.7229 (1.0); 7.7197 (1.1); 7.7153 (0.8); 7.6941 (1.2); 7.6886 (0.9); 7.6642 (0.5); 7.6598 (0.3); 7.6521 (1.9); 7.6490 (2.1); 7.6437 (2.5); 7.6402 (2.4); 7.6217 (1.1); 7.6015 (0.4); 7.3412 (0.5); 7.3340 (0.7); 7.3256 (0.7); 7.3189 (0.9); 7.3153 (0.8); 7.3129 (0.8); 7.3085 (0.5); 7.3005 (0.5); 7.2959 (0.6); 7.2899 (0.4); 3.9079 (16.0); 3.8911 (3.2); 3.8725 (3.2); 3.8540 (0.9); 3.3229 (65.9); 2.6753 (0.5); 2.6707 (0.7); 2.6662 (0.5); 2.5241 (2.1); 2.5106 (41.6); 2.5063 (83.6); 2.5018 (109.4); 2.4972 (79.2); 2.4928 (38.5); 2.3332 (0.5); 2.3286 (0.6); 2.3241 (0.5); 2.0750 (1.0); 1.2654 (3.4); 1.2470 (7.6); 1.2284 (3.3); ?0.0002 (0.4) I-17 [00025] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 9.0461 (7.4); 8.8626 (2.3); 8.8579 (2.4); 8.7394 (3.2); 8.7173 (4.0); 8.6871 (2.5); 8.6825 (2.4); 8.4878 (3.8); 8.4656 (3.5); 8.2664 (3.3); 8.2612 (3.4); 8.2383 (2.7); 8.2168 (3.4); 8.0630 (2.0); 8.0578 (1.8); 8.0416 (1.6); 8.0363 (1.6); 3.9903 (0.5); 3.9041 (16.0); 3.8904 (3.1); 3.8719 (3.0); 3.8527 (1.4); 3.8160 (0.4); 3.3217 (102.2); 2.6794 (0.5); 2.6751 (1.0); 2.6705 (1.4); 2.6659 (1.0); 2.6613 (0.5); 2.5240 (4.3); 2.5192 (6.5); 2.5106 (85.4); 2.5061 (173.2); 2.5015 (226.8); 2.4969 (162.8); 2.4924 (77.8); 2.3373 (0.4); 2.3330 (1.0); 2.3283 (1.4); 2.3237 (1.0); 2.3192 (0.4); 2.0747 (0.9); 1.2645 (3.4); 1.2461 (7.9); 1.2275 (3.4); 1.2053 (0.4); 0.0080 (2.3); ?0.0001 (72.0); ?0.0085 (2.3) I-18 [00026] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8815 (8.0); 8.8592 (2.2); 8.8545 (2.3); 8.7205 (3.2); 8.6983 (4.1); 8.6846 (2.3); 8.6798 (2.2); 8.5061 (3.9); 8.4840 (3.6); 8.1556 (1.7); 8.1511 (2.8); 8.1465 (1.8); 7.8326 (1.1); 7.8303 (1.4); 7.8288 (1.3); 7.8264 (1.1); 7.8128 (1.1); 7.8106 (1.5); 7.8090 (1.4); 7.8067 (1.3); 7.8008 (1.1); 7.7987 (1.2); 7.7956 (1.1); 7.7935 (1.0); 7.7804 (1.2); 7.7782 (1.1); 7.7751 (1.3); 7.7730 (1.0); 7.3912 (1.7); 7.3711 (2.9); 7.3510 (1.4); 3.9032 (16.0); 3.8860 (2.9); 3.8675 (2.9); 3.8490 (0.8); 3.3220 (56.0); 2.6753 (0.5); 2.6706 (0.8); 2.6661 (0.6); 2.5242 (2.0); 2.5194 (3.0); 2.5107 (44.0); 2.5062 (90.8); 2.5016 (120.3); 2.4970 (86.5); 2.4925 (41.1); 2.3330 (0.5); 2.3285 (0.7); 2.3239 (0.5); 2.0749 (6.6); 1.2638 (3.2); 1.2453 (7.5); 1.2268 (3.1); ?0.0002 (3.9) I-19 [00027] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.9140 (6.9); 8.8583 (2.1); 8.8535 (2.3); 8.7259 (3.2); 8.7038 (4.0); 8.6818 (2.2); 8.6772 (2.1); 8.5100 (3.7); 8.4879 (3.4); 7.9126 (1.6); 7.9075 (3.2); 7.9025 (1.7); 7.7758 (0.9); 7.7734 (1.1); 7.7708 (0.9); 7.7683 (0.9); 7.7556 (1.2); 7.7532 (1.3); 7.7505 (1.3); 7.7480 (1.2); 7.6341 (1.4); 7.6138 (2.9); 7.5936 (1.7); 7.5425 (1.3); 7.5401 (1.5); 7.5375 (1.4); 7.5351 (1.3); 7.5223 (0.8); 7.5199 (0.9); 7.5173 (0.9); 7.5149 (0.8); 4.2749 (0.6); 3.9084 (16.0); 3.8913 (2.9); 3.8728 (2.9); 3.8544 (0.8); 3.3256 (47.7); 2.6758 (0.5); 2.6712 (0.8); 2.6666 (0.5); 2.5247 (2.2); 2.5200 (3.1); 2.5113 (44.4); 2.5068 (91.8); 2.5023 (121.0); 2.4977 (86.0); 2.4931 (40.6); 2.3336 (0.5); 2.3291 (0.7); 2.3245 (0.5); 2.0749 (1.9); 1.2663 (3.2); 1.2478 (7.6); 1.2293 (3.3); 0.1458 (0.6); 0.0079 (4.2); ?0.0002 (139.5); ?0.0086 (4.4); ?0.0134 (0.5); ?0.1498 (0.6) I-20 [00028] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8598 (8.2); 8.8528 (2.4); 8.7172 (3.2); 8.6951 (4.0); 8.6828 (2.2); 8.6781 (2.2); 8.5052 (3.8); 8.4830 (3.5); 7.9604 (0.4); 7.9536 (4.2); 7.9485 (1.4); 7.9367 (1.4); 7.9316 (5.0); 7.9250 (0.6); 7.5865 (0.5); 7.5798 (4.8); 7.5746 (1.5); 7.5629 (1.4); 7.5577 (4.6); 7.5509 (0.5); 3.9015 (16.0); 3.8863 (2.9); 3.8678 (2.9); 3.8493 (0.9); 3.3449 (315.5); 2.6769 (0.4); 2.6723 (0.6); 2.6677 (0.5); 2.5258 (1.7); 2.5211 (2.6); 2.5124 (37.9); 2.5079 (78.8); 2.5033 (104.5); 2.4987 (74.6); 2.4941 (35.1); 2.3346 (0.4); 2.3301 (0.6); 2.3255 (0.4); 2.0751 (3.1); 1.2623 (3.2); 1.2439 (7.6); 1.2254 (3.2); ?0.0002 (8.5) I-21 [00029] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8678 (8.5); 8.8576 (6.7); 8.7539 (3.1); 8.7317 (4.2); 8.5783 (4.1); 8.5561 (3.6); 8.3157 (0.5); 7.7734 (3.9); 7.7684 (1.4); 7.7568 (1.5); 7.7516 (5.0); 7.7450 (0.6); 7.5550 (0.6); 7.5485 (4.7); 7.5435 (1.5); 7.5318 (1.4); 7.5266 (4.0); 7.5200 (0.4); 7.3079 (0.4); 4.0673 (16.0); 4.0555 (0.6); 4.0377 (1.1); 4.0199 (1.1); 4.0020 (0.4); 3.8281 (0.9); 3.8097 (3.0); 3.7912 (3.1); 3.7728 (0.9); 3.5679 (3.8); 3.3243 (216.5); 2.6798 (0.5); 2.6753 (1.1); 2.6708 (1.5); 2.6662 (1.1); 2.6617 (0.6); 2.5243 (4.2); 2.5195 (6.6); 2.5109 (89.0); 2.5064 (183.0); 2.5018 (242.5); 2.4972 (171.9); 2.4927 (80.9); 2.3378 (0.5); 2.3332 (1.0); 2.3286 (1.4); 2.3241 (1.0); 2.3196 (0.5); 1.9888 (4.9); 1.8303 (1.2); 1.8173 (3.1); 1.8104 (3.5); 1.7992 (1.4); 1.6001 (1.4); 1.5875 (3.4); 1.5806 (3.5); 1.5668 (1.1); 1.2616 (3.5); 1.2431 (8.3); 1.2246 (3.5); 1.1927 (1.4); 1.1749 (2.8); 1.1571 (1.3); 0.1459 (0.4); 0.0080 (3.0); ?0.0002 (95.0); ?0.0085 (3.2); ?0.1496 (0.4) I-22 [00030] : .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 8.8777 (8.1); 8.8526 (7.2); 8.7573 (3.2); 8.7351 (4.1); 8.5704 (4.0); 8.5481 (3.5); 7.8067 (0.4); 7.7994 (4.1); 7.7940 (1.4); 7.7825 (1.7); 7.7771 (5.9); 7.7698 (0.6); 7.6825 (0.7); 7.6753 (5.9); 7.6699 (1.6); 7.6583 (1.4); 7.6531 (4.1); 7.6455 (0.4); 4.0698 (16.0); 3.8301 (1.0); 3.8116 (3.3); 3.7931 (3.4); 3.7747 (1.0); 3.3191 (81.4); 2.6755 (0.6); 2.6710 (0.8); 2.6665 (0.6); 2.5242 (2.7); 2.5108 (47.0); 2.5065 (90.4); 2.5019 (116.0); 2.4974 (83.9); 2.4930 (40.9); 2.3332 (0.5); 2.3288 (0.7); 2.3243 (0.5); 2.0736 (0.4); 1.2635 (3.7); 1.2450 (8.3); 1.2266 (3.6); 0.1460 (0.5); 0.0160 (0.4); 0.0079 (4.8); ?0.0002 (121.8); ?0.0085 (4.5); ?0.1496 (0.5) I-23 [00031] : .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): ? = 8.8686 (7.2); 8.8552 (2.6); 8.8508 (2.9); 8.7213 (3.1); 8.6991 (3.9); 8.6777 (2.7); 8.6733 (2.8); 8.5078 (3.7); 8.4857 (3.3); 7.8046 (0.4); 7.7972 (4.0); 7.7920 (1.5); 7.7803 (1.6); 7.7749 (5.7); 7.7675 (0.8); 7.6786 (0.7); 7.6713 (5.6); 7.6660 (1.8); 7.6542 (1.4); 7.6490 (4.0); 5.7555 (8.1); 3.9076 (16.0); 3.8910 (3.3); 3.8724 (3.2); 3.8541 (1.0); 3.3194 (25.1); 2.6714 (0.4); 2.5111 (20.9); 2.5068 (43.0); 2.5023 (59.5); 2.4979 (45.8); 2.3292 (0.4); 1.9891 (1.1); 1.2659 (3.4); 1.2474 (7.7); 1.2289 (3.7); 1.1931 (0.4); 1.1753 (0.7); 1.1575 (0.3); 0.0080 (2.6); ?0.0001 (67.0); ?0.0083 (2.8) I-24 [00032] : .sup.1H-NMR(600.1 MHz, d.sub.6-DMSO): ? = 8.9314 (0.2); 8.9086 (5.9); 8.8556 (1.5); 8.8524 (1.5); 8.7178 (2.3); 8.7030 (2.8); 8.6778 (1.5); 8.6747 (1.4); 8.5157 (2.8); 8.5009 (2.7); 8.3138 (0.3); 8.3026 (3.7); 7.8288 (1.0); 7.8247 (0.5); 7.8180 (0.8); 7.8138 (4.8); 7.8050 (4.2); 7.8009 (0.6); 7.7939 (0.4); 7.7899 (0.9); 3.9698 (0.4); 3.9250 (16.0); 3.9093 (11.8); 3.8981 (0.6); 3.8858 (2.2); 3.8735 (2.2); 3.8611 (0.6); 3.3162 (151.8); 2.6194 (0.4); 2.6164 (0.8); 2.6133 (1.1); 2.6102 (0.8); 2.6073 (0.4); 2.5223 (2.4); 2.5193 (3.0); 2.5161 (2.7); 2.5074 (51.9); 2.5043 (115.3); 2.5013 (161.2); 2.4982 (114.0); 2.4951 (50.4); 2.3912 (0.3); 2.3882 (0.8); 2.3851 (1.0); 2.3821 (0.7); 2.3790 (0.3); 1.2606 (2.6); 1.2483 (5.9); 1.2360 (2.6); 0.0968 (0.4); 0.0054 (3.3); ?0.0001 (125.9); ?0.0057 (3.8); ?0.1003 (0.5)

Use Examples

Boophilus microplusInjection Test

[0492] Solvent: dimethyl sulfoxide

[0493] An appropriate active ingredient formulation is produced by mixing 10 mg of active ingredient with 0.5 ml of solvent and diluting the concentrate with solvent to the desired concentration.

[0494] 1 ?l of the active ingredient solution is injected into the abdomen of 5 engorged adult female cattle ticks (Boophilus microplus). The ticks are transferred into dishes and kept in a climate-controlled room.

[0495] Efficacy is checked after 7 days by laying of fertile eggs. Eggs which are not visibly fertile are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. Efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all the eggs are fertile.

[0496] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 ?g/tick: I-23.

Ctenocephalides felisOral Test

[0497] Solvent: dimethyl sulfoxide

[0498] An appropriate active ingredient formulation is produced by mixing 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide. Dilution with citrated cattle blood gives the desired concentration.

[0499] About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into a chamber which is closed at the top and bottom with gauze. Onto the chamber is placed a metal cylinder with its bottom end closed with parafilm. The cylinder contains the blood/active ingredient formulation, which can be imbibed by the fleas through the parafilm membrane. The cylinder is heated to 37? C., while the flea chambers are kept at room temperature.

[0500] After 2 days, the kill rate in % is determined relative to the untreated control. 100% means that all of the fleas have been killed; 0% means that none of the fleas have been killed.

[0501] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 1-22, 1-23.

Lucilia cuprina Test

[0502] Solvent: dimethyl sulfoxide

[0503] An appropriate active ingredient formulation is produced by mixing 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide and diluting the concentrate with water to the desired concentration.

[0504] About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) are transferred into a test vessel containing minced horsemeat and the active ingredient formulation of the desired concentration.

[0505] After 2 days, the kill rate in % is determined relative to the untreated control. 100% means that all the larvae have been killed; 0% means that no larvae have been killed.

[0506] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 1-22, 1-23.

Musca domestica Test

[0507] Solvent: dimethyl sulfoxide

[0508] An appropriate active ingredient formulation is produced by mixing 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide and diluting the concentrate with water to the desired concentration.

[0509] Vessels containing a sponge treated with sugar solution and the desired concentration of active compound formulation are populated with 10 adult houseflies (Musca domestica).

[0510] After 2 days, the kill rate in % is determined relative to the untreated control. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.

[0511] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 1-22, 1-23.

Diabrotica balteataSpray Test

[0512] Solvent: 78 parts by weight of acetone [0513] 1.5 parts by weight of dimethylformamide

[0514] Emulsifier: alkylaryl polyglycol ether

[0515] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water.

[0516] Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water for one day (5 seed grains per cavity). The germinated wheat grains are sprayed with an active ingredient formulation of the desired concentration. Subsequently, each cavity is infected with 10-20 beetle larvae of Diabrotica balteata.

[0517] After 7 days, efficacy in % is determined. 100% means that all wheat plants have grown as in the untreated, uninfected control; 0% means that no wheat plant has grown.

[0518] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 125 g/ha (=40 ?g/cavity): I-20, I-21.

[0519] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 g/ha (=32 ?g/cavity): I-01, I-02, I-03, I-04, I-05, I-06, I-07, I-08, I-09, I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, 1-18, I-19, I-24.

Meloidogyne incognita Test

[0520] Solvent: 125.0 parts by weight of acetone

[0521] An appropriate active ingredient formulation is produced by mixing 1 part by weight of active ingredient with the stated amount of solvent and diluting the concentrate to the desired concentration with water.

[0522] Vessels are filled with sand, active ingredient solution, an egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0523] After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0524] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 20 ppm: I-02, I-05, I-07, I-08, I-10, I-11, I-12, I-14, I-15, I-16.

[0525] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 ppm: I-09, I-17, I-20, I-21.

Myzus persicaeOral Test

[0526] Solvent: 100 parts by weight of acetone

[0527] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the specified parts by weight of solvent and making the solution up to the desired concentration with water.

[0528] 50 ?l of the active ingredient formulation is transferred into microtitre plates and made up to a final volume of 200 ?l with 150 ?l of IPL41 insect medium (33%+15% sugar). Subsequently, the plates are sealed with parafilm, which a mixed population of green peach aphids (Myzus persicae) within a second microtitre plate is able to puncture and imbibe the solution.

[0529] After 5 days, efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[0530] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 4 ppm: I-21, I-22, I-23.

[0531] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 4 ppm: I-17.

Nezara viridulaSpray Test

[0532] Solvent: 78.0 parts by weight of acetone [0533] 1.5 parts by weight of dimethylformamide

[0534] Emulsifier: alkylaryl polyglycol ether

[0535] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water.

[0536] Barley plants (Hordeum vulgare) are sprayed with an active ingredient formulation of the desired concentration and are infected with larvae of the Southern green shield bug (Nezara viridula).

[0537] After 4 days, efficacy in % is determined. 100% means that all of the shield bugs have been killed; 0% means that none of the shield bugs have been killed.

[0538] In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: I-02, I-04, I-06, I-07.

Phaedon cochleariaeSpray Test

[0539] Solvent: 78.0 parts by weight of acetone [0540] 1.5 parts by weight of dimethylformamide

[0541] Emulsifier: alkylaryl polyglycol ether

[0542] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water.

[0543] Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

[0544] After 7 days, efficacy in % is determined. 100% means that all the beetle larvae have been killed; 0% means that no beetle larvae have been killed.

[0545] In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: 1-22, 1-23.

Spodoptera FrusiperdaSpray Test

[0546] Solvent: 78.0 parts by weight of acetone [0547] 1.5 parts by weight of dimethylformamide

[0548] Emulsifier: alkylaryl polyglycol ether

[0549] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water.

[0550] Leaf discs of maize (Zea mays) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with caterpillars of the fall armyworm (Spodoptera frugiperda).

[0551] After 7 days, efficacy in % is determined. 100% means that all the caterpillars have been killed; 0% means that no caterpillar has been killed.

[0552] In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: I-01, I-04, I-05, I-06, I-07, I-08, I-09, I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-20, I-21, I-22, I-23, I-24.

Tetranychus urticaeSpray Test, OP-Resistant

[0553] Solvent: 78.0 parts by weight of acetone [0554] 1.5 parts by weight of dimethylformamide

[0555] Emulsifier: alkylaryl polyglycol ether

[0556] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water.

[0557] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active ingredient formulation of the desired concentration.

[0558] After 6 days, efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.

[0559] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 500 g/ha: I-03.

Diabrotica balteataDrench Test

[0560] Solvent: 7 parts by weight of dimethylformamide

[0561] Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

[0562] An appropriate active ingredient formulation is produced by mixing 1 part by weight of active ingredient with the specified amounts of solvent and emulsifier, and diluting the concentrate to the desired concentration with water, it being necessary to take account of the volume of soil which is drenched. It should be ensured that a concentration of 40 ppm of emulsifier in the soil is not exceeded. Further test concentrations are produced by diluting with water.

[0563] 5 maize cobs (Zea mays) in each case are sown into pots filled with earth, and the next day the pots are watered with the active ingredient preparation of the desired concentration. After one day, about 25 L2 larvae of the banded cucumber beetle (Diabrotica balteata) are added.

[0564] After 8 days, efficacy in % is determined. 100% means that all 5 plants have germinated and grown; 0% means that none of the plants has emerged.

[0565] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 20 ppm: 1-22, 1-23.

Myzus persicaeSpray Test

[0566] Solvent: 14 parts by weight of dimethylformamide

[0567] Emulsifier: alkylaryl polyglycol ether

[0568] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0569] Bell pepper plants (Capsicum annuum) severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active ingredient formulation in the desired concentration.

[0570] After 6 days, the kill rate in % is determined. 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

[0571] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 20 ppm: I-06.

[0572] In this test, for example, the following compounds from the preparation examples show an efficacy of 98% at an application rate of 20 ppm: I-12.

Nezara viridulaSpray Test

[0573] Solvent: 52.5 parts by weight of acetone [0574] 7 parts by weight of dimethylformamide

[0575] Emulsifier: alkylaryl polyglycol ether

[0576] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0577] Barley plants (Hordeum vulgare) infected with larvae of the Southern green shield bug (Nezara viridula) are sprayed with an active ingredient formulation of the desired concentration.

[0578] After 4 days, efficacy in % is determined. 100% means that all of the shield bugs have been killed; 0% means that none of the shield bugs have been killed.

[0579] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 g ai/ha: I-12, I-13, I-15, I-20, I-23.

[0580] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 g ai/ha: I-11, I-18, I-22.

Spodoptera FrustiperdaSpray Test

[0581] Solvent: 14 parts by weight of dimethylformamide

[0582] Emulsifier: alkylaryl polyglycol ether

[0583] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0584] Cotton leaves (Gossypium hirsutum) are sprayed with an active ingredient formulation of the desired concentration and populated with caterpillars of the armyworm (Spodoptera frugiperda).

[0585] After 7 days, the kill in % is determined. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed.

[0586] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 4 ppm: I-02.

Comparative Experiments

Plutella xylostella Spray Test (PLUTMA)

[0587] Solvent: 14 parts by weight of dimethylformamide

[0588] Emulsifier: alkylaryl polyglycol ether

[0589] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0590] Cabbage leaves (Brassica oleracea) are sprayed with an active ingredient formulation of the desired concentration and infected with larvae of the diamondback moth (Plutella xylostella).

[0591] After 7 days, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

[0592] In this test, for example, the following compounds from the preparation examples show superior efficacy to the prior art: see table.

Heliothis Armigera Spray Test (HELIAR)

[0593] Solvent: 14 parts by weight of dimethylformamide

[0594] Emulsifier: alkylaryl polyglycol ether

[0595] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0596] Cotton plants (Gossypium hirsutum) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with caterpillars of the cotton bollworm (Heliothis armigera).

[0597] After 7 days, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

[0598] In this test, for example, the following compound of the Preparation Examples shows superior efficacy to the prior art: see table

Spodoptera frugtiperdaSpray Test (SPODFR)

[0599] Solvent: 14 parts by weight of dimethylformamide

[0600] Emulsifier: alkylaryl polyglycol ether

[0601] An appropriate active ingredient formulation is produced by dissolving 1 part by weight of active ingredient with the stated parts by weight of solvent and making the solution up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations are produced by diluting the formulation with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0602] Cotton leaves (Gossypium hirsutum) are sprayed with an active ingredient formulation of the desired concentration and populated with caterpillars of the armyworm (Spodoptera frugiperda).

[0603] After 7 days, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

[0604] In this test, for example, the following compounds from the preparation examples show superior efficacy to the prior art: see table.

TABLE-US-00002 % Substance Structure Object Concentration Efficacy Ex. No. I-33 known from WO 2017/055185 [00033] PLUTMA SPODFR 0.16 ppm 0.8 ppm 15 0 Ex. No. I-23 inventive [00034] PLUTMA SPODFR 0.16 ppm 0.8 ppm 90 100 Ex. No. I-16 known from WO 2017/055185 [00035] PLUTMA SPODFR HELIAR HELIAR 0.8 ppm 0.8 ppm 4 ppm 0.8 ppm 85 10 60 20 Ex. No. I-14 inventive [00036] PLUTMA SPODFR HELIAR HELIAR 0.8 ppm 0.8 ppm 4 ppm 0.8 ppm 100 100 100 100