Heterocyclic Compounds as Pesticides

Abstract

The present application relates to novel heterocyclic compounds of the formula (I)

##STR00001##

in which G, R.sup.1, R.sup.2, Q and V have the meanings given in the description, to processes for their preparation and to their use for controlling animal pests.

Claims

1. A compound of formula (I) ##STR00035## in which G represents N or C-A.sup.1, A.sup.1 represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy or in each case optionally substituted cycloalkyl or cycloalkenyl, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00036##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents NR.sup.7R.sup.8, or represents an in each case optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S(O).sub.m-alkyl, R.sup.7—CO-alkyl, NR.sup.7R.sup.8—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, W represents a radical from the series O, S, SO and SO.sub.2, X represents a radical from the series hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and cycloalkyl, Y represents a radical from the series hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl and NR.sup.5R.sup.6, R.sup.2 represents hydrogen or alkyl, Q represents nitrogen or C—R.sup.3 in which R.sup.3 represents a radical from the series hydrogen, halogen, cyano, nitro, hydroxyl, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, cycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, SH, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphonyl, NH.sub.2, alkylamino and dialkylamino, V represents a radical from the series oxygen, sulphur and NR.sup.4 and R.sup.4 represents a radical from the series hydrogen, cyano, alkyl, haloalkyl, cycloalkyl, nitro, carbonylalkyl, carbonylhaloalkyl and carbonylalkoxy, R.sup.5 represents a radical from the series hydrogen, alkyl and haloalkyl, R.sup.6 represents a radical from the series hydrogen, alkyl and haloalkyl, or R.sup.5 and R.sup.6 together with the nitrogen to which they are bonded represent an optionally substituted saturated or unsaturated 3- to 6-membered ring which optionally contains further heteroatoms, R.sup.7 represents hydrogen, hydroxyl, or an in each case optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkyl-S(O).sub.m-alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, R.sup.8 represents hydrogen, a metal ion, an optionally substituted ammonium ion or an in each case optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkyl-S(O).sub.m— alkyl and m represents a number from 0, 1 and 2.

2. The compound of formula (I) according to claim 1, in which G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl and C.sub.3-C.sub.6-cycloalkyl, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00037##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents NR.sup.7R.sup.8 or represents C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkyl-S(O).sub.m—C.sub.1-C.sub.4-alkyl, each of which is optionally substituted by halogen or cyano, or represents R.sup.7—CO—C.sub.1-C.sub.4-alkyl, or represents NR.sup.7R.sup.8—CO—C.sub.1-C.sub.4-alkyl, or represents C.sub.3-C.sub.8-cycloalkyl, each of which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents C.sub.3-C.sub.8-cycloalkenyl, each of which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents heterocyclyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents heterocyclyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents phenyl, phenyl-C.sub.1-C.sub.4-alkyl, hetaryl and hetaryl-C.sub.1-C.sub.4-alkyl, each of which is optionally monosubstituted to trisubstituted by halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, m represents a number from 0, 1 and 2, W represents a radical from the series O, S, SO and SO.sub.2, X represents a radical from the series hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and C.sub.3-C.sub.6-cycloalkyl. Y represents a radical from the series hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkyl and NR.sup.5R.sup.6, R.sup.2 represents hydrogen or C.sub.1-C.sub.6-alkyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen, hydroxyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.4-alkyl, SH, C.sub.1-C.sub.6-alkylsulphanyl, C.sub.1-C.sub.6-alkylsulphinyl, C.sub.1-C.sub.6-alkylsulphonyl, NH.sub.2, C.sub.1-C.sub.6-alkylamino and di-(C.sub.1-C.sub.6-alkyl)-amino, V represents a radical from the series oxygen, sulphur and NR.sup.4, R.sup.4 represents a radical from the series hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-haloalkyl and C.sub.3-C.sub.6-cycloalkyl, R.sup.5 represents a radical from the series hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.2-C.sub.6-haloalkyl, R.sup.6 represents a radical from the series hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.2-C.sub.6-haloalkyl, R.sup.5 and R.sup.6 can also together with the nitrogen atom to which they are bonded represent a saturated to triunsaturated 3- to 6-membered ring which is optionally substituted by halogen, cyano, 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, R.sup.7 represents a radical from the series hydrogen, hydroxyl, or C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkyl-S(O).sub.m—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.3-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.3-alkyl, each of which is optionally monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by cyano, and represents phenyl, phenyl-C.sub.1-C.sub.3-alkyl, hetaryl and hetaryl-C.sub.1-C.sub.3-alkyl, each of which is optionally monosubstituted to tetrasubstituted by 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.3-C.sub.6-cycloalkyl, halogen or cyano, and R.sup.8 represents hydrogen, a metal ion, or represents an ammonium ion which is optionally monosubstituted to tetrasubstituted by C.sub.1-C.sub.4-alkyl, or represents a radical from the series C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-alkyl-S(O).sub.m-alkyl, each of which is optionally monosubstituted or polysubstituted by halogen or monsubstituted or disubstituted by cyano.

3. A compound of formula (I) according to claim 1, wherein G represents N or C-A.sup.1, A.sup.1 represents a radical from the series halogen, fluorine, chlorine, bromine, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00038##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents NR.sup.7R.sup.8, or represents C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.m—C.sub.1-C.sub.3-alkyl, each of which is optionally monosubstituted to heterosubstituted by halogen or monosubstituted or disubstituted by oxygen (leads to C═O) or monosubstituted or disubstituted by cyano, or represents R.sup.7—CO—C.sub.1-C.sub.2-alkyl, or represents NR.sup.7R.sup.8—CO—C.sub.1-C.sub.2-alkyl, or represents C.sub.3-C.sub.8-cycloalkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents C.sub.3-C.sub.8-cycloalkenyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents saturated or unsaturated C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents heterocyclyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents heterocyclyl-C.sub.1-C.sub.4-alkyl which is optionally monosubstituted or disubstituted by oxygen (leads to C═O), C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkyl, or represents phenyl, phenyl-C.sub.1-C.sub.3-alkyl, hetaryl and hetaryl-C.sub.1-C.sub.3-alkyl, each of which is optionally monosubstituted to trisubstituted by halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, iodine, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, iodine, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, R.sup.2 represents hydrogen or C.sub.1-C.sub.4-alkyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen, hydroxyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.4-haloalkoxy-C.sub.1-C.sub.3-alkyl, SH, C.sub.1-C.sub.4-alkylsulphanyl, C.sub.1-C.sub.4-alkylsulphinyl, C.sub.1-C.sub.4-alkylsulphonyl, NH.sub.2, C.sub.1-C.sub.4-alkylamino and di-(C.sub.1-C.sub.4-alkyl)-amino, V represents oxygen, R.sup.7 represents hydrogen, hydroxyl, or represents a radical from the series C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.m—C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.3-alkyl, each of which is optionally monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by cyano, and represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl, each of which is optionally monosubstituted to trisubstituted by C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano, and R.sup.8 represents hydrogen, a metal ion, or represents an ammonium ion optionally monosubstituted to tetrasubstituted by C.sub.1-C.sub.4-alkyl or a radical from the series C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.4-alkyl-S(O).sub.m—C.sub.1-C.sub.2-alkyl, each of which is optionally monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by cyano, m represents a number from the series 0, 1 and 2.

4. The compound of the formula (I) according to claim 1, in which G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl and 2,2-difluoroethyl, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00039##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents NR.sup.7R.sup.8, or represents a radical from the series C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-alkenyl, C.sub.3-C.sub.4-alkynyl, C.sub.1-C.sub.2-alkoxy-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.2-alkyl-S(O).sub.m—C.sub.1-C.sub.2-alkyl, each of which is optionally monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted by fluorine, chlorine or disubstituted by cyano, or represents R.sup.7—CO—C.sub.1-C.sub.2-alkyl, or represents NR.sup.7R.sup.8—CO—C.sub.1-C.sub.2-alkyl, or represents C.sub.3-C.sub.6-cycloalkyl which is optionally monosubstituted or disubstituted by halogen, cyano, C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl or by an oxygen atom (leads to C═O), or represents C.sub.3-C.sub.6-cycloalkenyl which is optionally monosubstituted or disubstituted by C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl or by an oxygen atom (leads to C═O), or represents C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.2-alkyl which is optionally monosubstituted to disubstituted by halogen, cyano, C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl, or represents C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.2-alkyl which is optionally monosubstituted or disubstituted by C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl, or represents heterocyclyl which is optionally monosubstituted or disubstituted by C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl, or represents heterocyclyl-C.sub.1-C.sub.2-alkyl which is optionally monosubstituted or disubstituted by C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.2-haloalkyl, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl or thiazolylmethyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, R.sup.2 represents hydrogen or methyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen, methyl, trifluoromethyl and cyclopropyl, V represents oxygen, R.sup.7 represents a radical from the series hydrogen, hydroxyl, or C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.m—C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, heterocyclyl and heterocyclyl-C.sub.1-C.sub.3-alkyl which is optionally monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentasubstituted by fluorine, chlorine or monosubstituted or disubstituted by cyano, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl, each of which is optionally monosubstituted to trisubstituted by C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano, R.sup.8 represents hydrogen, an alkali or alkaline-earth metal ion, an ammonium ion which is optionally monosubstituted to tetrasubstituted by C.sub.1-C.sub.4-alkyl, or represents a radical from the series C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl and C.sub.1-C.sub.4-alkyl-S(O).sub.m—C.sub.1-C.sub.2-alkyl, each of which is optionally monosubstituted or polysubstituted by fluorine, chlorine or is monosubstituted or disubstituted by cyano, and m represents a number from series 0, 1 and 2.

5. The compound of formula (I) according to claim 1, wherein G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen and fluorine, T represents an electron pair or oxygen, R.sup.1 represents the radical from the series ##STR00040##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl, propargyl, 2-butynyl, each of which is optionally monosubstituted, disubstituted or trisubstituted by fluorine or monosubstituted by cyano, or represents C.sub.3-C.sub.6-cycloalkyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or represents C.sub.3-C.sub.6-cycloalkylmethyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy or trifluoromethyl, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl and pyridinylmethyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy, R.sup.2 represents hydrogen or methyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen, methyl, trifluoromethyl and cyclopropyl, V represents oxygen.

6. The compound of formula (I) according to claim 1, wherein G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen and fluorine, T represents an electron pair, R.sup.1 represents the radical of the formula ##STR00041##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl, propargyl, 2-butynyl, each of which is optionally monosubstituted, disubstituted or trisubstituted by fluorine or monosubstituted by cyano, or represents C.sub.3-C.sub.6-cycloalkyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or represents C.sub.3-C.sub.6-cycloalkylmethyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy or trifluoromethyl, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl and pyridinylmethyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, R.sup.2 represents hydrogen or methyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen and methyl, V represents oxygen.

7. The compound of formula (I) according to claim 1, wherein G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen and fluorine, T represents an electron pair, R.sup.1 represents the radical of the formula ##STR00042##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl, propargyl, 2-butynyl, each of which is optionally monosubstituted, disubstituted or trisubstituted by fluorine or monosubstituted by cyano, or represents C.sub.3-C.sub.6-cycloalkyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or represents C.sub.3-C.sub.6-cycloalkylmethyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy or trifluoromethyl, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl and pyridinylmethyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, R.sup.2 represents hydrogen or methyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen and methyl, V represents oxygen.

8. The compound of formula (I) according to claim 1, wherein G represents N or C-A.sup.1, A.sup.1 represents a radical from the series hydrogen or fluorine, T represents an electron pair, R.sup.1 represents the radical of the formula ##STR00043##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl, propargyl, 2-butynyl, each of which is optionally monosubstituted, disubstituted or trisubstituted by fluorine or monosubstituted by cyano, or represents C.sub.3-C.sub.6-cycloalkyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or represents C.sub.3-C.sub.6-cycloalkylmethyl which is optionally monosubstituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy or trifluoromethyl, or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl and pyridinylmethyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, W represents a radical from the series S, SO and SO.sub.2, X represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, Y represents a radical from the series hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl and trifluoromethyl, R.sup.2 represents hydrogen or methyl, Q represents nitrogen or C—R.sup.3, R.sup.3 represents a radical from the series hydrogen and methyl, V represents oxygen.

9. The compound of formula (I) according to claim 1, wherein G represents C-A.sup.1, A.sup.1 represents hydrogen, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00044##  in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents a radical from the series methyl, trifluoroethyl and cyclopropylmethyl, W represents a radical from the series S and SO, X represents a radical from the series hydrogen, fluorine, chlorine and methyl, Y represents a radical from the series hydrogen, chlorine and methyl, R.sup.2 represents hydrogen, Q represents nitrogen or C—R.sup.3, R.sup.3 represents hydrogen or methyl and V represents oxygen.

10. A composition, comprising a content of at least one compound of the formula (I) according to claim 1 and one or more customary extenders and/or surface-active substances.

11. The compound of formula (I) according to claim 1 for controlling pests.

12. The compound of formula (II) ##STR00045## in which G represents N or C-A.sup.1, A.sup.1 represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy or in each case optionally substituted cycloalkyl or cycloalkenyl, T represents an electron pair or oxygen, R.sup.1 represents the radical of the formula ##STR00046## in which the bond with the nitrogen atom in the C(═V)—N-Q group in formula (I) is marked by the asterisk (*), R represents NR.sup.7R.sup.8, or represents an in each case optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S(O).sub.m-alkyl, R.sup.7—CO-alkyl, NR.sup.7R.sup.8—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, W represents a radical from the series O, S, SO and SO.sub.2, X represents a radical from the series hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and cycloalkyl, Y represents a radical from the series hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl and NR.sup.5R.sup.6, R.sup.2 represents hydrogen or alkyl, Q represents nitrogen or C—R.sup.3 in which R.sup.3 represents a radical from the series hydrogen, halogen, cyano, nitro, hydroxyl, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, cycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, SH, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphonyl, NH.sub.2, alkylamino and dialkylamino, V represents a radical from the series oxygen, sulphur and NR.sup.4 and R.sup.4 represents a radical from the series hydrogen, cyano, alkyl, haloalkyl, cycloalkyl, nitro, carbonylalkyl, carbonylhaloalkyl and carbonylalkoxy, R.sup.5 represents a radical from the series hydrogen, alkyl and haloalkyl, R.sup.6 represents a radical from the series hydrogen, alkyl and haloalkyl, or R.sup.5 and R.sup.6 together with the nitrogen to which they are bonded represent an optionally substituted saturated or unsaturated 3- to 6-membered ring which optionally contains further heteroatoms, R.sup.7 represents hydrogen, hydroxyl, or an in each case optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkyl-S(O).sub.m-alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, R.sup.8 represents hydrogen, a metal ion, an optionally substituted ammonium ion or an in each case optionally substituted radical from the series alkyl, alkoxy, alkoxyalkyl, alkyl-S(O).sub.m— alkyl and m represents a number from 0, 1 and 2

13. The compound of formula (VIII-1) ##STR00047##

Description

PREPARATION EXAMPLES

Example 1

5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (I-1-1)

Step 1: 3-Amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1-(pyridin-3-yl)-1H-pyrazole-4-carboxamide (II-1)

[0345] ##STR00024##

[0346] 2.09 ml of a 2M trimethylaluminium solution in toluene were slowly added dropwise to 500 mg (2.09 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline in 1.3 ml 1,2-dichloroethane, and the mixture was stirred for 1 hour (h) at room temperature. 562 mg (2.09 mmol) of ethyl-3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1) were added to 1.3 ml of 1,2-dichloroethane, and the reaction mixture was refluxed overnight. After cooling, the reaction mixture was diluted with water and carefully poured into a 10% potassium sodium tartrate solution. The mixture was extracted by shaking three times with methylene chloride, and the organic phase was removed, dried over sodium sulphate, filtered and concentrated. The residue was adsorbed onto silica gel and purified by preparative MPLC over a silica gel cartridge (mobile phase cyclohexane/ethyl acetate). The isolated fraction gave 551 mg (purity 100% as per LC/MS, 62% of theory) of the title compound.

[0347] log P[a]: 2.72; log P[b]: 2.63; 1H NMR (D6-DMSO 400 MHz) δ ppm: 9.61 (d, 1H), 9.05 (s, 1H), 8.95 (d, 1H), 8.49-8.48 (m, 1H), 8.06-8.02 (m, 1H), 7.91 (d, 1H), 7.57-7.53 (m, 1H), 7.29 (d, 1H), 5.89 (s, 2H), 3.85 (q, 2H), 2.41 (s, 3H)

Step 2: 5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (I-1-1)

[0348] ##STR00025##

[0349] 34.0 mg (0.20 mmol) of p-toluenesulphonic acid and 200 μl (178 mmol, 1.20 mmol) of triethyl orthoformate were added to 170 mg (0.40 mmol) of 3-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluorethyl)sulphanyl]phenyl}-1-(pyridin-3-yl)-1H-pyrazole-4-carboxamide (II-1) in 2 ml of N,N-dimethylacetamide. The reaction mixture was heated to 130° C. at 200 watts in a CEM Discover microwave for 1 h. After cooling, the reaction mixture was mixed with RP-18 material, and the solvent was removed under reduced pressure. The residue was purified over an RP-18 cartridge by means of preparative MPLC (mobile phase water/acetonitrile). The isolated fraction contained 80.0 mg (purity 96% according to LC/MS, 44% of theory) of the title compound.

[0350] log P[a]: 2.65; log P[b]: 2.63; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 9.59 (d, 1H), 9.29 (s, 1H), 8.68 (dd, 1H), 8.47-8.44 (m, 1H), 8.36 (s, 1H), 7.87 (d, 1H), 7.68-7.64 (m, 1H), 7.46 (d, 1H), 4.03 (q, 2H), 2.46 (s, 3H)

Example 2

3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-6-(3-pyridyl)pyrazolo[3,4-d]triazin-4-one (I-1-2) and 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-6-(3-pyridyl)pyrazolo[3,4-d]triazin-4-one (I-1-3)

[0351] ##STR00026##

[0352] A solution of 248 mg (3.60 mmol) of sodium nitrite in 5 ml of water was added dropwise to 180 mg (0.42 mmol) of 3-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1-(pyridin-3-yl)-1H-pyrazole-4-carboxamide (II-1) in 5 ml of water and 5 ml of concentrated hydrochloric acid. The mixture was stirred at 70° C. for 6 hours. After cooling, the reaction mixture was poured into methylene chloride, and the pH was adjusted to 7 with concentrated sodium bicarbonate solution. The mixture was extracted three times with methylene chloride, and the combined organic phases were washed with water, dried over sodium sulphate, filtered and concentrated. The residue was adsorbed onto RP-18 and purified by preparative MPLC (mobile phase water/acetonitrile) over an RP-18 cartridge. The isolated fractions contained 64.0 mg (purity 100% according to LC/MS, 33% of theory) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-6-(3-pyridyl)pyrazolo[3,4-d]triazin-4-one (I-1-2) and 72.0 mg (purity 100% according to LC/MS, 39% of theory) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-6-(3-pyridyl)pyrazolo[3,4-d]triazin-4-one (I-1-3).

[0353] (I-1-2) log P[a]: 2.22; log P[b]: 2.19; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 9.84 (s, 1H), 9.37 (s, 1H), 9.36 (d, 1H), 8.78-8.76 (m, 1H), 8.20 (d, 1H), 7.75-7.71 (m, 1H), 7.64 (d, 1H), 4.39-4.01 (m, 2H), 3H under the DMSO peak.

[0354] (I-1-3) log P[a]: 3.18; log P[b]: 3.14; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 9.84 (s, 1H), 9.36 (s, 1H), 8.78-8.76 (m, 1H), 8.56-8.53 (d, 1H), 7.95 (d, 1H), 7.75-7.71 (m, 1H), 7.52 (d, 1H), 3.99 (q, 2H), 3H under the DMSO peak.

Example 3

5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyridin-3-yl)-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (I-1-4)

[0355] ##STR00027##

[0356] 35.4 mg (0.14 mmol) of meta-chloroperbenzoic acid were added at 0° C. to a solution of 61.0 mg (0.14 mmol) of 5-{2-fluoro-4-methyl-5-[(2,2,2-trifluorethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (I-1-1) in 3 ml of methylene chloride. The reaction mixture was stirred for 2 hours at room temperature and then diluted with methylene chloride and treated with concentrated sodium bicarbonate solution. After 10 minutes, the phases were separated, the organic phase was mixed with RP-18 material, and the solvent was removed under reduced pressure. The residue was purified by preparative MPLC (mobile phase water/acetonitrile) over an RP-18 cartridge. The isolated fraction contained 36.0 mg (purity 98.5% according to LC/MS, 56% of theory) of the title compound.

[0357] log P[a]: 1.79; log P[b]: 1.78; 1H NMR (D6-DMSO 400 MHz) δ ppm: 9.60 (s, 1H), 9.30 (d, 1H), 8.68 (d, 1H), 8.47-8.42 (m, 2H), 8.11 (d, 1H), 7.67-7.65 (m, 1H), 7.58 (d, 1H), 4.35-4.05 (m, 2H), 3H under the DMSO peak

Example 4

5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(1-oxidopyridin-1-ium-3-yl)pyrazolo[3,4-d]pyrimidin-4-one (I-1-5)

[0358] ##STR00028##

[0359] 119 mg (0.48 mmol) of meta-chloroperbenzoic acid were added at 0° C. to a solution of 100 mg (0.23 mmol) of 5-{2-fluoro-4-methyl-5-[(2,2,2-trifluorethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (I-1-1) in 3 ml of methylene chloride. The reaction mixture was stirred overnight at room temperature and subsequently treated with 28.0 mg (0.12 mmol) of meta-chloroperbenzoic acid. After a further night at room temperature, the reaction mixture was diluted with methylene chloride and treated with concentrated sodium bicarbonate solution. After 10 minutes, a solid was filtered off with suction and washed with water and dichloromethane and dried. The solid contained 43.0 mg (purity 78% according to LC/MS, 31% of theory) of the title compound.

[0360] log P[a]: 1.39; log P[b]: 1.33; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 9.60 (s, 1H), 9.02 (s, 1H), 8.44 (s, 1H), 8.31 (d, 1H), 8.11 (d, 1H), 8.03 (d, 1H), 7.65-7.57 (m, 2H), 4.32-4.05 (m, 2H), 3H under the DMSO peak

Synthesis of Intermediates

Ethyl 5-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (IIIa-1) and ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1) by process B

[0361] ##STR00029##

[0362] 82.3 g (0.59 mol) of potassium carbonate were initially charged in a three-neck flask. The flask was baked out under argon and the following were added in succession: 2.70 g (0.014 mol) of copper(I) iodide, 44.0 g (0.28 mol) of ethyl 3-amino-4-pyrazolecarboxylate and 440 ml of N,N-dimethylacetamide. The suspension was stirred for 10 minutes and then 7.18 g (0.056 mol) of trans-1,2-diaminocyclohexane and 53.77 g (0.34 mol) of 3-bromopyridine were added. The reaction mixture was brought to reflux temperature and stirred at 145° C. overnight. After cooling, the reaction mixture was filtered off with suction, the mother liquor was concentrated and the residue was purified by means of MPLC using an RP(C-18) column with acetonitrile/water/0.1% formic acid. A first fraction contained 39 g of a mixture of 70% ethyl 5-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (IIIa-1) and 30% ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1), according to LC/MS. A second fraction contained 10 g, consisting of 83% ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (IIIb-1) according to LC/MS. A separation of (IIIa-1) and (III-1) from the first fraction by means of preparative HPLC gave a further 24.5 g (96% purity) of ethyl 5-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate as the formate (IIIa-1) and 11.5 g (99% purity) of ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1).

[0363] (IIIa-1).HCOOH log P[a]: 1.18; log P[b]: 1.27; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 12.8 (bs, 1H), 8.78 (d, H), 8.62 (dd, 1H), 8.14 (s, H), 7.99-7.96 (m, 1H), 7.76 (s, 1H), 7.58 (dd, H), 6.51 (bs, 2H), 4.23 (q, 2H), 1.28 (t, 3H)

[0364] (III-1) log P[a]: 1.12; log P[b]: 1.32; 1H NMR (D6-DMSO, 400 MHz) δ ppm: 9.06 (d, 1H), 8.86 (s, 1H), 8.47 (d, H), 8.19 (bd, H), 7.49 (dd, 1H), 5.78 (bs, 2H), 4.26 (q, 2H), 1.30 (t, 3H)

Ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1) by process C

Step 1: Benzaldehyde pyridin-3-yl hydrazone (VII-1)

[0365] ##STR00030##

[0366] To 15.00 g (103.0 mol) of 3-hydrazinopyridine hydrochloride (1:1) and 9.49 g (68.7 mmol) of potassium carbonate in 150 ml of toluene were slowly added 7 ml (68.7 mmol) of benzaldehyde dissolved in 100 ml of toluene. The reaction mixture was stirred under reflux (with a water separator) overnight. After cooling, the insoluble fractions were filtered off with suction. The solid residue was stirred repeatedly in ethyl acetate. The solids were filtered off with suction and stirred repeatedly in hot isopropanol. The insoluble fractions were filtered off with suction and discarded; the filtrate was concentrated. The resulting 5.50 g (98% pure, 40% of theory) of the title compound were converted further directly.

[0367] log P[a]: 0.86; log P[b]: 2.22

Step 2: Ethyl 3-[2-benzylidene-1-(pyridin-3-yl)hydrazino]-2-cyanoacrylate (VIII-1)

[0368] ##STR00031##

[0369] To 5.50 g (27.9 mmol) of benzaldehyde pyridin-3-yl hydrazone in 14 ml of toluene were added 4.72 g (27.9 mmol) of ethyl 2-cyano-3-ethoxyacrylate. The reaction mixture was heated under reflux first for 2 h and, after addition of a spatula-tip of para-toluenesulphonic acid, for a further 2 h. After cooling, the precipitated solids were filtered off with suction and the organic phase was discarded. The solids were initially charged once again in 15 ml of toluene and admixed with 1.69 g (10.0 mmol) of ethyl 2-cyano-3-ethoxyacrylate. The reaction mixture was heated overnight under reflux, left to stand until cold and subsequently diluted with toluene. After addition of approximately 0.5 ml of acetonitrile, the insoluble residue was filtered off with suction and dried under vacuum. 3.11 g (purity 90%, 31% of theory) of the title compound were isolated.

[0370] log P[a]: 2.54; log P[b]: 2.48

Step 3: Ethyl 3-amino-1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (III-1)

[0371] ##STR00032##

[0372] 3.00 g (9.37 mmol) of ethyl 3-[2-benzylidene-1-(pyridin-3-yl)hydrazino]-2-cyanoacrylate were initially charged in 11 ml of ethanol, and 1.1 ml (13.11 mmol) of a 37% hydrochloric acid solution were added. The reaction mixture was heated under reflux for 1 h, cooled and then concentrated. The residue was stirred twice in lukewarm toluene. The solids were filtered off with suction and dried under reduced pressure. 2.64 g (purity 92%, 97% of theory) of the title compound were isolated.

[0373] Further compounds of the formula (I) are compiled in the table which follows.

TABLE-US-00001 TABLE 1 Compounds of the formula (I-1) (I-1) [00033] in which V represents oxygen, R.sup.2 represents hydrogen and the remaining variables have the meanings stated in the table Ex. No. G Q R X Y W T I-1-1 CH CH CF.sub.3CH.sub.2 2-F 4-CH.sub.3 S — I-1-2 CH N CF.sub.3CH.sub.2 2-F 4-CH.sub.3 SO — I-1-3 CH N CF.sub.3CH.sub.2 2-F 4-CH.sub.3 S — I-1-4 CH CH CF.sub.3CH.sub.2 2-F 4-CH.sub.3 SO — I-1-5 CH CH CF.sub.3CH.sub.2 2-F 4-CH.sub.3 SO O I-1-6 CH CH CH.sub.3 H H S — I-1-7 CH CH CF.sub.3CH.sub.2 H 4-CH.sub.3 S — I-1-8 CH CH CF.sub.3CH.sub.2 H 4-CH.sub.3 SO — I-1-9 CH CH CF.sub.3CH.sub.2 2-F H S — I-1-10 CH CH CF.sub.3CH.sub.2 2-F H SO — I-1-11 CH CH cPrCH.sub.2 H H S — I-1-12 CH CH CF.sub.3CH.sub.2 H H S — I-1-13 CH CH CF.sub.3CH.sub.2 2-F 4-Cl S — I-1-14 CH CH CF.sub.3CH.sub.2 2-Cl 4-Cl S — I-1-15 CH CH CF.sub.3CH.sub.2 2-Cl 4-Cl SO O I-1-16 CH CH CF.sub.3CH.sub.2 H H SO — I-1-17 CH CH CF.sub.3CH.sub.2 2-CH.sub.3 4-CH.sub.3 S — I-1-18 CH CH CF.sub.3CH.sub.2 2-F 4-Cl SO — I-1-19 CH CH CF.sub.3CH.sub.2 2-Cl 4-Cl SO — I-1-20 CH CH CF.sub.3CH.sub.2 2-CH.sub.3 4-CH.sub.3 SO — I-1-21 CH CH cPrCH.sub.2 H H SO — I-1-22 CH C—CH.sub.3 CF.sub.3CH.sub.2 2-F 4-CH.sub.3 S —

TABLE-US-00002 TABLE 2 Analytical data for the compounds reported Ex. No. logP[a] logP[b] 1H-NMR (D6-DMSO, 400 MHz) σ (ppm) I-1-6 1.82 1.78 9.58(s, 1H), 9.30(d, 1H), 8.67(d, 1H), 8.46(d, 1H), 8.34(s, 1H), 7.67-7.64(m, 1H), 7.51-7.38(m, 3H), 7.27(d, 1H), 3H under the DMSO peak I-1-7 2.51 2.56 9.58(s, 1H), 9.30(s, 1H), 8.68-8.67(m1H), 8.46(d, 1H), 8.31(s, 1H), 7.70-7.64(m, 2H), 7.43(d, 1H), 7.33(d, 1H), 4.08(q, 2H), 2.42(s, 3H) I-1-8 1.65 1.67 9.59(s, 1H), 9.31(d, 1H), 8.67(d, 1H), 8.45(dd, 1H), 8.41(s, 1H), 7.96(d, 1H), 7.69-7.64(m, 2H), 7.56(d, 1H), 4.26-4.10(m, 2H), 2.47(s, 3H) I-1-9 2.32 2.35 9.61(s, 1H), 9.30(d, 1H), 8.68(dd, 1H), 8.48-8.44(m, 1H), 8.39(s, 1H), 7.88(dd, 1H), 7.74-7.71(m, 1H), 7.68- 7.64(m, 1H), 7.51(t, 1H), 4.10(q, 2H) I-1-10 1.53 1.55 9.63(s, 1H), 9.30(d, 1H), 8.68(dd, 1H), 8.48-8.43(m, 2H), 8.15-8.14(m, 1H), 8.05-8.01(m, 1H), 7.80(t, 1H), 7.68- 7.65(m, 1H), 4.35-4.10(m, 2H)

TABLE-US-00003 TABLE 3 Compounds of the formula (I-2) (I-2) [00034] in which V represents oxygen, R.sup.2 represents hydrogen and the remaining variables have the meanings stated in the table: Ex. No. G Q R X Y W T I-2-23 CH CH CH.sub.3 H H S —

NMR Data of Selected Examples

NMR Peak List Method

[0374] The 1H NMR data of selected examples are stated in the form of 1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ value—signal intensity—number pairs for different signal peaks are listed with separation from one another by semicolons.

[0375] The peak list for one example therefore takes the form of:

δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; (intensity.sub.i); . . . ; δ.sub.n, (intensity.sub.n)

[0376] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0377] For calibration of the chemical shift of the 1H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0378] The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0379] In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject matter of the invention, and/or peaks of impurities.

[0380] In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-d.sub.6 and the peak of water, which usually have a high intensity on average.

[0381] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0382] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of our preparation process with reference to “by-product fingerprints”.

[0383] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation.

[0384] Further details of 1H NMR peak lists can be found in Research Disclosure Database Number 564025.

TABLE-US-00004 Ex. No. logP [b] logP [a] I-1-11 2.41 2.50 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.574(15.4); 9.300(5.3); 9.294(5.4); 8.677(3.7); 8.674(4.0); 8.665(3.9); 8.662(4.0); 8.475(2.3); 8.472(2.7); 8.468(2.6); 8.465(2.3); 8.454(2.5); 8.451(2.7); 8.448(2.9); 8.444(2.4); 8.330(16.0); 7.670(3.2); 7.658(3.1); 7.649(3.1); 7.637(3.0); 7.501(2.2); 7.493(4.4); 7.489(7.9); 7.482(10.1); 7.462(8.9); 7.453(3.9); 7.450(6.3); 7.446(3.9); 7.434(1.6); 7.430(2.2); 7.306(2.7); 7.302(4.1); 7.298(2.8); 7.288(2.4); 7.283(3.3); 7.279(2.3); 7.120(2.8); 7.100(2.5); 3.332(56.6); 3.331(57.8); 3.008 (12.4); 2.990(12.6); 2.676(0.5); 2.672(0.7); 2.667(0.5); 2.525(2.5); 2.507(84.9); 2.503(110.7); 2.498(82.7); 2.334(0.6); 2.329(0.8); 2.325(0.6); 2.288(10.6); 1.103(0.6); 1.096(0.7); 1.091(0.5); 1.084(1.4); 1.077(1.3); 1.073(1.1); 1.065(2.3); 1.057(1.1); 1.053(1.4); 1.046(1.5); 1.034(0.8); 1.027(0.6); 0.571(1.9); 0.560(5.8); 0.556(6.2); 0.546(3.0); 0.540(6.0); 0.536(5.7); 0.526(2.2); 0.302(2.3); 0.292(6.7); 0.288(6.7); 0.280(6.1); 0.276(7.0); 0.265(1.9); 0.008(2.3); 0.000(57.8); −0.008(2.5) I-1-12 2.18 2.25 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.826(1.1); 9.587(15.8); 9.306(6.6); 9.300(6.8); 9.006(1.9); 8.958(0.9); 8.952(0.9); 8.677(5.0); 8.668(4.8); 8.666(5.0); 8.499(0.8); 8.479(3.2); 8.476(3.2); 8.473(2.9); 8.461(2.8); 8.458(3.3); 8.455(3.4); 8.452(2.9); 8.344(16.0); 8.065(0.4); 8.043(0.5); 7.861(1.1); 7.696(8.2); 7.675(3.7); 7.663(3.7); 7.654(3.6); 7.642(3.6); 7.630(3.4); 7.610(5.7); 7.594(0.9); 7.573(0.8); 7.562(4.3); 7.552(1.0); 7.543(6.9); 7.523(3.4); 7.482(0.9); 7.462(1.0); 7.439(4.6); 7.418(3.4); 7.381(0.6); 7.361(1.0); 7.342(0.6); 7.260(0.7); 7.240(0.5); 7.119(0.8); 7.099(0.7); 4.172(2.6); 4.146(8.0); 4.120(8.3); 4.094(2.9); 4.027(0.4); 4.001(1.3); 3.975(1.3); 3.950(0.5); 3.437(3.4); 3.387(4.5); 2.944(0.8); 2.784(0.7); 2.672(0.8); 2.565(0.7); 2.551(1.5); 2.537(1.4); 2.507(98.1); 2.503(126.9); 2.499(102.5); 2.330(0.9); 2.287(2.9); 2.076(0.9); 1.958(0.8); 0.000(13.4) I-1-13 2.65 2.70 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.798(0.4); 9.619(16.0); 9.299(6.6); 9.292(6.7); 8.688(4.5); 8.686(4.8); 8.676(4.7); 8.674(4.8); 8.474(2.5); 8.471(2.9); 8.468(2.8); 8.465(2.6); 8.454(2.8); 8.450(3.0); 8.448(3.1); 8.444(2.6); 8.378(15.3); 8.071(6.0); 8.053(5.9); 7.918(6.7); 7.894(6.7); 7.678(3.7); 7.667(3.6); 7.658(3.6); 7.646(3.5); 4.214(1.8); 4.189(5.5); 4.163(5.7); 4.138(2.0); 3.330(72.0); 2.945(1.7); 2.785(1.5); 2.672(0.9); 2.507(101.2); 2.503(131.6); 2.499(99.0); 2.334(0.6); 2.330(0.9); 2.288(0.8); 1.958(1.6); 1.630(0.5); 0.146(0.4); 0.007(3.8); 0.000(88.1); −0.008(4.5); −0.060(0.5); −0.150(0.5) I-1-14 2.83 2.91 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.609(16.0); 9.293(9.4); 8.689(7.2); 8.678(7.2); 8.466(5.1); 8.446(5.3); 8.321(16.0); 8.078(14.9); 8.045(15.1); 7.680(4.6); 7.669(4.9); 7.659(4.8); 7.648(4.3); 7.482(1.1); 7.464(1.2); 7.122(1.2); 7.102(1.1); 4.308(0.4); 4.282(1.1); 4.266(1.9); 4.242(4.9); 4.226(5.4); 4.216(5.5); 4.201(5.0); 4.176(1.8); 4.162(1.1); 4.137(0.4); 3.524(0.3); 3.498(0.4); 3.473(0.6); 3.346(468.3); 3.229(0.7); 2.945(1.7); 2.786 (1.7); 2.674(1.3); 2.504(198.5); 2.400(0.5); 2.374(0.4); 2.331(1.4); 2.289(3.3); 2.075(5.2); 1.959(1.7); 0.146(0.4); 0.000(79.6); −0.149(0.5) I-1-15 1.67 1.66 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.621(12.4); 9.602(10.7); 9.346(0.3); 9.025(7.3); 9.021(8.4); 9.017(7.9); 8.509(2.0); 8.443(0.3); 8.413(1.9); 8.361(10.9); 8.344(2.5); 8.318(16.0); 8.307(8.0); 8.273(9.6); 8.256(11.5); 8.231(12.9); 8.212(10.7); 8.045(6.2); 8.023(6.8); 7.903(1.8); 7.898(1.5); 7.894(1.1); 7.887(1.1); 7.720(0.6); 7.699(0.8); 7.656(6.2); 7.640 (6.7); 7.635(6.5); 7.619(5.3); 7.568(0.9); 7.548(1.4); 7.528(0.6); 5.187(0.3); 5.163(1.0); 5.139(1.0); 5.114(0.4); 4.556(0.4); 4.529(1.3); 4.518(0.6); 4.502(1.5); 4.492(1.7); 4.475(0.7); 4.465(1.6); 4.437(0.5); 4.343(0.4); 4.316(1.1); 4.306(1.0); 4.289(1.3); 4.280(2.7); 4.268(1.1); 4.263(1.0); 4.253(2.8); 4.242(2.6); 4.226(1.2); 4.214(2.7); 4.204(1.5); 4.187(1.2); 4.176(2.3); 4.165(0.7); 4.149(2.0); 4.138(1.5); 4.122(0.8); 4.112(1.4); 4.085(0.5); 3.327(160.1); 2.945(0.7); 2.785(0.7); 2.671(1.9); 2.506(232.5); 2.502(287.1); 2.329(1.9); 1.958(0.7); 1.235(0.8); 0.000(32.0); −0.062(0.4) I-1-16 1.41 1.46 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.613(15.2); 9.312(5.4); 9.306(5.4); 9.072(0.5); 8.682(3.7); 8.679(4.0); 8.671(3.9); 8.667(4.1); 8.612(0.4); 8.603(0.4); 8.487(2.1); 8.484(2.4); 8.480(2.3); 8.477(2.1); 8.466(2.3); 8.463(2.4); 8.459(2.6); 8.456(2.2); 8.431(16.0); 8.191(0.4); 7.967(3.4); 7.963(6.4); 7.959(4.1); 7.932(2.0); 7.928(3.3); 7.924(1.8); 7.914(2.7); 7.910(4.7); 7.906(2.6); 7.854(2.2); 7.834(5.5); 7.815(4.6); 7.808(5.7); 7.804(3.3); 7.793(1.2); 7.789(1.7); 7.784(0.9); 7.676(2.9); 7.664(2.8); 7.655(2.8); 7.643(3.0); 7.628(0.4); 7.622(0.6); 7.618(0.4); 7.603(0.4); 7.491(0.4); 4.307(1.0); 4.298(0.8); 4.280(1.3); 4.271(2.6); 4.253(1.0); 4.244(2.7); 4.229(2.5); 4.217(1.2); 4.202(2.8); 4.193(1.3); 4.176(1.1); 4.166(1.2); 4.139(0.4); 3.355(0.3); 3.331(124.0); 2.676(0.6); 2.672(0.8); 2.667(0.6); 2.525(1.9); 2.512(47.3); 2.507(96.4); 2.503(126.6); 2.498(92.1); 2.494(45.1); 2.334(0.6); 2.329(0.8); 2.325(0.6); 0.146(1.0); 0.024(0.4); 0.008(7.4); 0.000(205.8); −0.009(7.8); −0.150(1.0) I-1-17 2.72 2.75 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.568(5.9); 9.291(4.2); 8.680(3.2); 8.670(3.2); 8.464(2.4); 8.446(2.5); 8.220(5.7); 7.674(2.2); 7.662(2.5); 7.655(2.5); 7.643(2.2); 7.609(5.6); 7.333(5.1); 4.044(1.7); 4.019(4.1); 3.993(4.1); 3.967(1.6); 3.334(29.9); 2.670(0.6); 2.503(62.1); 2.398(15.5); 2.330(0.8); 2.288(0.4); 2.061(16.0); 0.000(10.6) I-1-18 1.94 2.02 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.626(16.0); 9.302(6.0); 9.296(6.2); 8.689(4.3); 8.686(4.5); 8.677(4.5); 8.674(4.5); 8.478(2.3); 8.474(2.7); 8.471(2.6); 8.468(2.3); 8.457(2.5); 8.453(2.8); 8.450(2.9); 8.447(2.4); 8.420(14.4); 8.226(5.6); 8.207(5.6); 8.107(4.8); 8.084(4.8); 7.681(3.2); 7.669(3.1); 7.660(3.1); 7.648(3.1); 5.758(0.5); 4.350(0.6); 4.342(0.6); 4.244(0.8); 4.217(0.9); 3.331(66.1); 2.677(0.5); 2.672(0.7); 2.668(0.5); 2.526(1.6); 2.512(39.6); 2.508(79.2); 2.503(103.5); 2.499(76.3); 2.334(0.5); 2.330(0.7); 2.325(0.5); 1.233(0.4); 0.008(1.0); 0.000(30.7); −0.008(1.3) I-1-19 2.09 2.17 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.629(16.0); 9.609(13.3); 9.300(11.0); 9.293(11.2); 8.690(7.5); 8.687(7.8); 8.678(7.8); 8.675(7.8); 8.472(4.6); 8.470(4.4); 8.466(3.9); 8.455(4.2); 8.451(4.7); 8.449(4.8); 8.446(4.0); 8.350(13.0); 8.318(0.6); 8.307(16.0); 8.276(11.5); 8.259(13.8); 8.240(0.3); 8.228(15.6); 8.207(12.9); 7.681(5.9); 7.669(5.7); 7.660(5.7); 7.648(5.6); 5.758(7.1); 4.559(0.4); 4.532(1.3); 4.522(0.6); 4.504(1.6); 4.494(1.8); 4.477(0.7); 4.467(1.8); 4.440(0.6); 4.321(1.0); 4.311(0.9); 4.294(1.2); 4.284(2.9); 4.267(0.7); 4.257(3.2); 4.251(3.0); 4.224(3.0); 4.214(1.6); 4.197(1.2); 4.188(2.6); 4.177(0.6); 4.161(2.2); 4.151(1.5); 4.134(0.8); 4.124(1.5); 4.098(0.5); 3.331 (128.7); 2.677(0.9); 2.672(1.2); 2.668(0.9); 2.526(3.5); 2.508(135.1); 2.503(174.8); 2.499(128.7); 2.335(0.8); 2.330(1.1); 2.326(0.8); 1.234(0.9); 0.008(2.1); 0.000(52.5) I-1-20 1.79 1.84 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.595(7.7); 9.579(4.9); 9.303(4.9); 9.297(5.0); 8.683(3.5); 8.671(3.6); 8.478(1.9); 8.474(2.3); 8.471(2.2); 8.468(1.9); 8.457(2.1); 8.453(2.3); 8.451(2.3); 8.447(1.9); 8.296(8.1); 8.278(5.1); 8.144(0.6); 7.862(5.8); 7.849(3.7); 7.677(2.6); 7.665 (2.5); 7.656(2.6); 7.644(2.5); 7.470(2.8); 7.447(4.3); 5.757(0.9); 4.306(0.5); 4.278(0.6); 4.269(0.7); 4.241(0.7); 4.177(0.9); 4.150(2.9); 4.123(3.0); 4.095(1.1); 4.012(0.6); 3.985(0.7); 3.975(0.6); 3.948(0.6); 3.328(25.6); 2.676(0.5); 2.672(0.6); 2.507(71.2); 2.503(89.7); 2.499(67.4); 2.445(10.4); 2.438(14.4); 2.399(0.4); 2.339(0.6); 2.334(0.6); 2.330(0.7); 2.325(0.6); 2.294(0.8); 2.276(0.3); 2.262(0.7); 2.167(16.0); 2.061(0.4); 0.146(0.4); 0.008(4.4); 0.000(85.5); −0.008(4.5); −0.149(0.4) I-1-21 1.32 1.27 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.600(6.6); 9.594(16.0); 9.308(7.3); 9.302(7.6); 9.081(0.3); 9.067(0.3); 8.680(5.5); 8.677(5.0); 8.668(5.7); 8.666(5.1); 8.482(3.1); 8.479(3.5); 8.476(3.3); 8.461(3.2); 8.458(3.6); 8.455(3.5); 8.424(5.8); 8.405(15.9); 8.317(0.5); 8.088(1.5); 8.084(2.6); 8.080(1.8); 8.034(1.3); 8.014(1.5); 7.940(0.9); 7.935(0.7); 7.923(1.2); 7.918(1.5); 7.873(1.8); 7.854(2.3); 7.833(7.2); 7.829(5.1); 7.823(2.1); 7.819(2.6); 7.803(3.8); 7.800(6.1); 7.796(3.5); 7.786(3.8); 7.767(5.9); 7.748(2.8); 7.714(3.0); 7.710(4.4); 7.705(2.8); 7.695(1.9); 7.691(2.7); 7.687(1.7); 7.674(3.8); 7.662(3.8); 7.653(3.8); 7.641(3.8); 7.577(0.3); 3.360(3.6); 3.342(4.6); 3.329(133.8); 3.269(0.4); 3.251(0.3); 2.948(0.4); 2.930(0.6); 2.914(5.6); 2.910(5.7); 2.897(5.3); 2.891(5.5); 2.877(0.6); 2.858(0.6); 2.676(1.0); 2.672(1.4); 2.667(1.0); 2.525(3.6); 2.507(152.2); 2.503(199.4); 2.498(149.5); 2.447(0.4); 2.438(0.3); 2.334(1.0); 2.329(1.4); 2.325(1.0); 1.514(0.5); 1.299(1.6); 1.259(2.3); 1.234(4.5); 1.216(0.6); 1.209(0.7); 1.022(0.4); 1.016(0.7); 1.004(1.3); 0.997(1.2); 0.985(2.0); 0.973(1.3); 0.966(1.4); 0.954(0.9); 0.947(0.6); 0.935(0.5); 0.917(0.6); 0.910(0.5); 0.899 (0.8); 0.887(0.6); 0.879(0.7); 0.868(0.6); 0.861(0.6); 0.853(0.8); 0.842(0.5); 0.836(0.5); 0.609(0.3); 0.586(1.6); 0.575(5.7); 0.566(3.2); 0.555(5.7); 0.546(1.9); 0.533(0.5); 0.523(0.5); 0.507(0.7); 0.496(1.8); 0.491(2.0); 0.476(2.0); 0.471(2.0); 0.460(0.8); 0.371(0.7); 0.365(1.0); 0.360(1.2); 0.353(1.3); 0.340(2.8); 0.328(2.6); 0.313(0.7); 0.300(0.5); 0.286(2.6); 0.273(2.8); 0.265(1.1); 0.260(1.4); 0.253(1.3); 0.249(1.0); 0.242(0.6); 0.162(0.7); 0.151(2.2); 0.148(2.2); 0.136(2.5); 0.124(0.8); 0.008(1.1); 0.000(31.6); −0.008(1.4) I-1-22 2.69 2.74 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.532(7.3); 9.278(3.0); 9.272(3.1); 8.671(2.2); 8.668(2.2); 8.659(2.3); 8.657(2.2); 8.445(1.2); 8.442(1.4); 8.439(1.3); 8.424(1.3); 8.421(1.4); 8.418(1.5); 8.155(1.7); 7.876(2.6); 7.857(2.7); 7.668(1.6); 7.656(1.6); 7.647(1.7); 7.635(1.6); 7.494 (2.4); 7.468(2.3); 4.100(0.5); 4.086(0.5); 4.074(0.7); 4.060(1.3); 4.035(1.5); 4.015(1.4); 3.989(1.4); 3.976(0.7); 3.963(0.6); 3.950(0.6); 3.326(70.9); 2.671(2.1); 2.506(252.6); 2.502(322.0); 2.498(247.4); 2.457(14.9); 2.416(0.7); 2.328(2.2); 2.242(0.4); 2.205(0.3); 2.178(16.0); 2.150(0.4); 2.075(5.3); 0.146(1.3); 0.008(12.9); 0.000(279.4); −0.034(0.4); −0.150(1.3) I-2-23 1.67 1.65 .sup.1H NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.571(6.2); 9.293(2.2); 9.287(2.2); 8.681(1.6); 8.678(1.6); 8.670(1.7); 8.666(1.6); 8.469(0.9); 8.465(1.0); 8.462(1.0); 8.458(0.9); 8.448(1.0); 8.444(1.0); 8.441(1.1); 8.438(0.9); 8.170(6.5); 7.673(1.2); 7.661(1.2); 7.652(1.2); 7.640(1.1); 7.585 (0.5); 7.582(0.6); 7.565(1.4); 7.562(1.3); 7.547(1.3); 7.544(1.4); 7.527(1.9); 7.524(2.1); 7.507(1.0); 7.504(0.8); 7.496(1.4); 7.493(1.4); 7.477(2.0); 7.474(1.7); 7.392(1.1); 7.388(1.0); 7.373(1.3); 7.370(1.3); 7.355(0.7); 7.351(0.6); 3.332(15.7); 2.944(1.1); 2.785(0.9); 2.511(13.3); 2.507(25.8); 2.503(33.0); 2.498(23.5); 2.494(11.2); 2.442(16.0); 2.075(0.5); 1.958(0.9); 0.008(2.0); 0.000(45.7); −0.009(1.7)

Biological Examples

[0385] Musca domestica Test (MUSCDO)
Solvent: dimethyl sulphoxide

[0386] To prepare an appropriate active ingredient preparation, 10 mg of active ingredient are mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate is diluted with water to the desired concentration.

[0387] Vessels containing a sponge treated with sugar solution and the active ingredient preparation of the desired concentration are populated with 10 adult houseflies (Musca domestica).

[0388] After 2 days, the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.

[0389] In this test, for example, the following compounds of the Preparation Examples showed an efficacy of 80% at an application rate of 100 ppm: I-1-2, I-1-3.

Myzus persicae—Spray Test (MYZUPE)
Solvent: 78 parts by weight of acetone [0390] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0391] To produce an appropriate active ingredient preparation, 1 part by weight of active ingredient is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0392] Discs of Chinese cabbage leaves (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active ingredient preparation of the desired concentration.

[0393] After 6 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that none of the aphids have been killed.

[0394] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-1-2, I-1-3, I-1-4, I-1-5, I-1-10, I-1-11.

[0395] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: I-1-6, I-1-7, I-1-8, I-1-12, I-1-14, I-1-15, I-1-16, I-1-17, I-1-18, I-1-19, I-1-21, I-1-22, I-2-23.

[0396] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 g/ha: I-1-9.

[0397] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 g/ha: I-1-20.

Tetranychus urticae—Spray Test, OP-Resistant (TETRUR)
Solvent: 78.0 parts by weight of acetone [0398] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0399] To produce an appropriate active ingredient preparation, 1 part by weight of active ingredient is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0400] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

[0401] After 6 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that none of the spider mites have been killed.

[0402] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-1-4.

[0403] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: I-1-20.

Myzus Persicae—Spray Test (MYZUPE)

[0404] Solvent: 7 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0405] To produce an appropriate active ingredient preparation, 1 part by weight of active ingredient is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted 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 preparation solution.

[0406] Bell pepper plants (Capsicum annuum) severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active ingredient preparation in the desired concentration.

[0407] After 6 days, the kill in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[0408] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 20 ppm: I-1-1.

[0409] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 4 ppm: I-1-13.