Triazolinethione-phosphoric acid derivatives

[0001] The present invention relates to novel triazolimethione-phosphoric acid derivatives, to a process for their preparation and to their use as microbicides.

[0002] It is already known that numerous alkylthio-triazolyl derivatives have fungicidal properties (cf WO 96-16 048). Thus, for example, 2-(1-chlorocyclopropyl)-1-(2-chloro-phenyl)-3-(5-methylthio-1,2,4-triazol-1-yl)-propan-2-ol can be employed for controlling fungi. The activity of this substance is good, but it is sometimes unsatisfactory at low application rates.

[0003] This invention, accordingly, provides novel triazolinethione-phosphoric acid derivatives of the formula

[0004] in which

[0005] R1 and R2 independently of one another each represent alkyl, halogenoalkyl, alkoxy, alkoxyalkoxy, halogenoalkoxy, alkoxyalkyl, alkylthio, alkenlylthio, alkinylthio, cycloalkyl, cycloalkyltlhio, optionally substituted phenyl, optionally substituted phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, optionally substituted phenoxy, optionally substituted phenylthio, optionally substituted phenylalkoxy having 1 to 4 carbon atoms in the alkoxy moiety, optionally substituted heteroaryl or represent a radical of the formula

[0006] in which

[0007] R4 represents hydrogen or alkyl and

[0008] R5 represents alkyl, optionally substituted phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety or represents optionally substituted phenyl or

[0009] R4 and R5 together represent an alkylene chain having 4 or 5 carbon atoms or represent a radical of the formula —CH2—CH2—O—CH2—CH2— or

[0010] in which

[0011] R6 represents hydrogen or alkyl having 1 to 4 carbon atoms,

[0012] R3 represents a radical of the formula

[0013] in which

[0014] R7 and R8 are identical or different and each represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aroxyalkyl, optionally substituted aryl or optionally substituted heteroaryl,

[0015] or

[0016] R3 represents a radical of the formula

[0017] in which

[0018] R9 represents alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms anid 1 to 5 halogen atoms, optionally halogen-substituted cycloalkyl having 3 to 7 carbon atoms, naphthyl or represents phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, phenyl, phenoxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, and

[0019] R10 represents phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms,

[0020] or

[0021] R3 represents a radical of the formula

[0022] in which

[0023] R11 and R12 independently of one another each represent hydrogen or alkyl having 1 to 6 carbon atoms,

[0024] X1 represents halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 4 carbon atoms, phenyl, phenoxy, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms or represents halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, and

[0025] m represents the numbers 0, 1 or 2,

[0026] or

[0027] R3 represents a radical of the formula

[0028] in which

[0029] R13 and R14 independently of one another each represent hydrogen or alkyl having 1 to 6 carbon atoms,

[0030] X2 represents halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms or phenyl,

[0031] n represents the numbers 0, 1 or 2 and

[0032] p represents the numbers 0, 1 or 2,

[0033] or

[0034] R3 represents a radical of the formula

[0035] in which

[0036] R15 represents alkyl having 2 to 18 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, naphthyl or the radical of the formula

[0037] in which

[0038] X3 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms and

[0039] q represents the numbers 0, 1 or 2,

[0040] R16 and R17 independently of one another each represent alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or represent the radical of the formula

[0041] in which

[0042] Y1 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms and

[0043] r represents the numbers 0, 1 or 2,

[0044] or

[0045] R3 represents a radical of the formula

[0046] in which

[0047] R18 represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, optionally substituted aryl or represents optionally substituted aralkyl,

[0048] or

[0049] R3 represents a radical of the formula

[0050] in which

[0051] R19 represents hydrogen, alkyl or optionally substituted cycloalkyl,

[0052] X4 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms,

[0053] s represents the numbers 0, 1, 2 or 3 and

[0054] Y2 represents an oxygen atom, a CH2 group or a direct bond,

[0055] or

[0056] R3 represents a radical of the formula

[0057] in which

[0058] R20 represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7 carbon atoms which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, optionally halogen-substituted phenyl or represents optionally halogen-substituted benzyl,

[0059] X5 represents halogen, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms,

[0060] t represents the numbers 0, 1, 2 or 3 and

[0061] Y3 represents an oxygen atom or represents a CH2 group, or

[0062] R3 represents a radical of the formula

[0063] in which

[0064] A represents alkanediyl having 2 or 3 carbon atoms which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms,

[0065] X6 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, and

[0066] u represents the numbers 0, 1 2 or 3, or

[0067] R3 represents a radical of the formula

[0068] in which

[0069] R21 represents alkyl having 1 to 10 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, fluoroalkoxyalkyl having 1 to 4 carbon atoms in the fluoroalkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, cycloalkyl having 3 to 7 carbon atoms which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, optionally halogen-substituted phenyl or represents optionally halogen-substituted phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,

[0070] X7 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenioalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, and

[0071] v represents the numbers 0, 1, 2 or 3, or

[0072] R3 represents a radical of the formula

[0073] in which

[0074] R22 represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7 carbon atoms which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, optionally halogen-substituted phenyl or represents optionally halogen-substituted benzyl,

[0075] X8 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkythio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms,

[0076] w represents the numbers 0, 1, 2 or 3 and

[0077] Y4 represents an oxygen atom or represents a CH2 group, or

[0078] R3 represents a radical of the formula

[0079] in which

[0080] R23 represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, optionally substituted aryl or represents optionally substituted aralkyl,

[0081] X9 represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthiio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or represents phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms and

[0082] z represents the numbers 0, 1, 2 or 3 and

[0083] Q represents oxygen or sulphur, and their metal salt complexes.

[0084] Numerous substances according to the invention contain one or more asymmetrically substituted carbon atoms. They can therefore be obtained in the form of optical isomers. The present invention relates both to the individual isomers and to their mixtures.

[0085] Furthermore, it has been found that triazolinethione-phosphoric acid derivatives of the formula (1) and their metal salt complexes are obtained when triazolinethiones of the formula

[0086] in which

[0087] R3 is as defined above, are reacted with phosphoric acid derivatives of the formula

[0088] in which

[0089] R1, R2 and Q are each as defined above

[0090] in the presence of an acid binder and, if appropriate, in the presence of a diluent

[0091] and, if appropriate, a metal salt is subsequently added to the resulting compounds of the formula (1).

[0092] Finally, it has been found that the novel triazolinethione-phosphoric acid derivatives of the formula (1) and their metal salt complexes have very good microbicidal properties and can be used both in crop protection and in the protection of materials for controlling undesirable microorganisms.

[0093] Surprisingly, the substances according to the invention have better microbicidal activity, in particular fungicidal activity, then 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methylthio-1,2,4-triazol-1-yl)-propan-2-ol, which is a constitutionally similar active compound of the prior art having the same direction of action.

[0094] The formula (1) provides a general definition of the triazolinethione-phosphoric acid derivatives according to the invention.

[0095] R1 preferably represents straight-chain or branched alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, straight-chain or branched alkoxy having 1 to 6 carbon atoms, all,oxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety, alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, or represents phenyl which may be mono- to trisubstitutedI by identical or different substituenits from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, hialogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or represents phenoxy which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or represents phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, where the phenyl moiety may be mono- to tristibstittited by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phentyl, nitro and cyano, or represents a five- or six-memberedi heteroaromatic radical having 1 or 2 heteroatoms, such as nitrogen, sulphur and/or oxygen, where each of these radicals may be mono- or disubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or

[0096] R1 represents a radical of the formula

[0097] in which

[0098] R4 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms and

[0099] R5 preferably represents alkyl having 1 to 6 carbon atoms or represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different stibstituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or

[0100] R5 preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or

[0101] R4 and R5 together represent an alkylene chain having 4 or 5 carbon atoms or represent a radical of the formula —CH2—CH2—O—CH2—CH2— or

[0102] in which

[0103] R6 represents hydrogen, methyl or ethyl.

[0104] R2 preferably represents straight-chain or branched alkoxy having 1 to 6 carbon atoms, cycloalkoxy having 3 to 6 carbon atoms, alkoxyalkoxy having 1 to 4 carbon atoms in each alkoxy moiety or represents phenoxy which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano, or represents phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano,

[0105] or represents five- or six-membered heteroaryloxy having 1 or 2 heteroatoms, such as nitrogen, sulphur and/or oxygen, in the heterocycle, where each of these radicals may be mono- or disubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl, nitro and cyano.

[0106] R3 preferably represents a radical of the formula

[0107] in which

[0108] R7 preferably represents straight-chain or branched alkyl having 1 to 6 carbon atoms, where these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, alkoxy having 1 to 4 carbon atoms, alkoximino having 1 to 4 carbon atoms in the alkoxy moiety and cycloalkyl having 3 to 7 carbon atoms, or

[0109] represents straight-chain or branched alkenyl having 2 to 6 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkoxy having 1 to 4 carbon atoms and cycloalkyl having 3 to 7 carbon atoms, or

[0110] represents cycloalkyl having 3 to 7 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano and alkyl having 1 to 4 carbon atoms, or

[0111] represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, where the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0112] represents aralkenyl having 6 to 10 carbon atoms in the aryl moiety and 2 to 4 carbon atoms in the alkenyl moiety, where the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0113] represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chain or branched oxyalkyl moiety, where the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0114] represents atryl having 6 to 10 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthlio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0115] represents an optionally benzo-fused, five- or six-membered hetero-aromatic radical having 1 to 3 heteroatoms, such as nitrogen, sulphur and/or oxygen, where each of these radicals may be mono- to trisubstituted by identical or different radicals from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinyl having 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group, acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in alkoxy moiety and 1 to 3 carbon atoms in alkyl moiety, nitro and cyano, and

[0116] R8 preferably represents straight-chain or branched alkyl having 1 to 6 carbon atoms, where these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, alkoxy having 1 to 4 carbon atoms, alkoximino having 1 to 4 carbon atoms in the alkoxy moiety and cycloalkyl having 3 to 7 carbon atoms, or

[0117] represents straight-chain or branched alkenyl having 2 to 6 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkoxy having 1 to 4 carbon atoms and cycloalkyl having 3 to 7 carbon atoms, or

[0118] represents cycloalkyl having 3 to 7 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano and alkyl having 1 to 4 carbon atoms, or

[0119] represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, where the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in (the alkyl moiety, nitro and cyano, or

[0120] represents aralkenyl having 6 to 10 carbon atoms in the aryl moiety and 2 to 4 carbon atoms in the alkenyl moiety, vhere the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0121] represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chain or branched oxyalkyl moiety, where the aryl moiety may in each case be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms andl 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0122] represents aryl having 6 to 10 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitro and cyano, or

[0123] represents an optionally benzo-fused, five- or six-membered hetero-aromatic radical having 1 to 3 heteroatoms, such as nitrogen, sulphur and/or oxygen, where each of these radicals may be mono- to trisubstituted by identical or different radicals from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinyl having 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 carbon atoms, halogenoalkyl, hialogenoalkoxy and halogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxy group, acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atoms in alkoxy moiety and 1 to 3 carbon atoms in alkyl moiety, nitro and cyano.

[0124] R3 furthermore preferably represents a radical of the formula

[0125] , in which

[0126] R9 preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, cycloalkyl having three to six carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, represents naphthyl or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio, and

[0127] R10 preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, isoprropyl, tert-butyl, methoxy, ethoxy, trifluroromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio.

[0128] R3 furthermore preferably represents a radical of the formula

[0129] R11 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

[0130] R12 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

[0131] X1 preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, phenyl, phenoxy, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or trifluoromethyl and

[0132] m also preferably represents the numbers 0, 1 or 2,

[0133] where X1 may represent identical or different radicals if m represents 2.

[0134] R3 furthermore preferably represents a radical of the formula

[0135] R13 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

[0136] R14 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

[0137] X2 preferably represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, trichloromethoxy, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or phenyl,

[0138] n also preferably represents the numbers 0 or 1 and

[0139] p also preferably represents the numbers 0, 1 or 2,

[0140] where X2 may represent identical or different radicals if p represents 2.

[0141] R3 furthermore preferably represents a radical of the formula

[0142] R15 preferably represents alkyl having 2 to 12 carbon atoms, cycloalkyl having 5 or 6 carbon atoms or represents a radical of the formula

[0143] in which

[0144] X3 preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy and

[0145] q also preferably represents the numbers 0, 1 or 2, where X3 represents identical or different radicals if g represents 2,

[0146] R16 preferably represents alkyl having 1 to 4 carbon atoms or represents the radical of the formula

[0147] in which

[0148] Y1 preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy and

[0149] r also preferably represents the numbers 0, 1 or 2, where Y1 represents identical or different radicals if r represents 2, and

[0150] R17 preferably represents alkyl having 1 to 4 carbon atoms.

[0151] R3 furthermore preferably represents a radical of the formula

[0152] in which

[0153] R18 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4 catbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, represents cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl, represents phenyl, benzyl or phenethyl, where each of the three last-mentioned radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or phenoxy which is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms.

[0154] R3 furthermore preferably represents a radical of the formula

[0155] in which

[0156] R19 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 12 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms,

[0157] X4 preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

[0158] s preferably represents the numbers 0, 1, 2 or 3, where X4 represents identical or different radicals if s represents 2 or 3, and

[0159] Y2 preferably represents an oxygen atom, a CH2 group or a direct bond.

[0160] R3 furthermore preferably represents a radical of the formula

[0161] in which

[0162] R20 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine or represents benzyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine,

[0163] X5 preferably represents fluorine, chlorine, bromine, nitro, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifltuoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which is optionally mono- or disubstituted by identical or different sutbstituents from the group consisting of fluorine, chlorine, bromine and methyl or represents phenoxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl,

[0164] t preferably represents the numbers 0, 1, 2 or 3, where X5 represents identical or different radicals if t represents 2 or 3 and

[0165] Y3 preferably represents an oxygen atom or represents a CH2 group.

[0166] R3 furthermore preferably represents a radical of the formula

[0167] in which

[0168] A preferably represents alkanediyl having 2 or 3 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl and tert-butyl,

[0169] X6 preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethoxy, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl or represents phenoxy which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl and

[0170] u preferably represents the numbers 0, 1, 2 or 3, where X6 represents identical or different radicals if u represents 2 or 3.

[0171] R3 furthermore preferably represents a radical of the formula

[0172] in which

[0173] R2 preferably represents straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, fluoroalkoxyalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine atoms in the fluoroalkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety, cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine or phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituled by identical or different substituents from the group consisting of fluorine, chlorine and bromine,

[0174] X7 preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthlio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl or represents phenoxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl and

[0175] v preferably represents the numbers 0, 1, 2 or 3, where X7 represents identical or different radicals if v represents 2 or 3.

[0176] R3 furthermore preferably represents a radical of the formula

[0177] R22 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 to 3 carbon atoms in alkyl moiety, phenyl which is optionally mono- to trisubstituted by identical or different stibstituents from the group consisting of fluorine, chlorine and bromine or represents benzyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine,

[0178] X8 preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl or represents phenoxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl,

[0179] w preferably represents the numbers 0, 1, 2 or 3, where X8 represents identical or different radicals if w represents 2 or 3, and

[0180] Y4 preferably represents an oxygen atom or represents a CH2 group.

[0181] R3 moreover also preferably represents a radical of the formula

[0182] in which

[0183] R23 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms having 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 halogen aitoms, alkoxy having 1 to 4 carbon atoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms,

[0184] X9 preferably represents fluorine, chlorine, bromine, methyl ethiyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethioxy, trifluoromethylthio, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl or represents phenoxy which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine and methyl and

[0185] z preferably represents the numbers 0, 1, 2 or 3, where X9 represents identical or different radicals if z represents 2 or 3.

[0186] Q preferably represents sulphur.

[0187] R1 particularly preferably represents straight-chain or branched alkyl having 1 to 5 carbon atoms, cyclopentyl, cyclohexyl, straight-chain or branched alkoxy having 1 to 5 carbon atoms, alkoxyalkoxy having 1 or 2 carbon atoms in each alkoxy moiety, alkoxyalkyl having 1 or 2 carbon atoms in the alkoxy moiety and 1 or 2 carbon atoms in the alkyl moiety,

[0188] or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano, or represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano, or represents phenoxy which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethlyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano, or represents phenylakoxy having 1 or 2 carbon atoms in the alkoxy moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano, or represents pyridyl, pyrrolyl, thienyl or furanyl, where each of these radicals may be mono- or disubstituted by identical or different substittuents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano,

[0189] or

[0190] R1 represents a radical of the formula

[0191] in which

[0192] R4 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl or n-butyl and

[0193] R5 particularly preferably represents alkyl having 1 to 4 carbon atoms or represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano,

[0194] R5 particiularly preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluorometlhyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano,

[0195] or

[0196] R4 and R5 together represent an alkylene chain having 4 or 5 carbon atoms or represent a radical of the formula —CH2—CH2—O—CH2—CH2— or

[0197] in which

[0198] R6 represents hydrogen, methyl or ethyl,

[0199] R2 particularly preferably represents straight-chain or branched alkoxy having 1 to 5 carbon atoms, cyclopentyloxy, cyclohexyloxy, alkoxyalkoxy having 1 or 2 carbon atoms in each alkoxy moiety, or represents phenyloxy which may be mono- to tristibstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluorometlhyl, trichlorometlhyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano,

[0200] or represents phenylalkoxy having 1 or 2 carbon atoms in the alkoxy moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluorometlyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano, or represents pyridyloxy, pyrrolyloxy, thienyloxy or furanyloxy, where each of these radicals may be mono- or diSLIt)stituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, phenyl, nitro and cyano.

[0201] R3 particularly preferably represents a radical of the formula

[0202] in which

[0203] R7 particularly preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, sphere these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbon atoms in alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

[0204] or

[0205] represents straight-chain or branched alkenyl having 2 to 5 carbon atoms, wvhere each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

[0206] or

[0207] represents cycloalkyl having 3 to 6 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, isopropyl and tert-butyl,

[0208] or

[0209] represents phenylalkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substiluents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

[0210] or

[0211] represents phenylalkenyl having 2 to 4 carbon atoms in the alkenyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

[0212] or

[0213] represents phenoxyalkyl having 1 to 4 carbon atoms in the straight-chain or branched oxyalkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different stibstituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, dilluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano, represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethiyl, 1-methoximinoethyl, nitro and cyano,

[0214] or

[0215] represents pyrazolyl, imidazolyl, 1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl or benzimidazolyl, which each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, chlorodifluoromethtylhio, hydroxymethyl, hydroxyethyl, hydroxyalkinyl having 4 to 6 carbon atoms, methoxycarbonyl, ethoxycarbonyl, methoximinomethlyl, 1-methoximinoethyl, nitro and cyano, formyl, dimethoxymethyl, acetyl and propionyl, and

[0216] R8 paiticularly preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, where these radicals may be mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbon atoms in alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

[0217] or

[0218] represents straight-chain or branched alkenyl having 2 to 5 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

[0219] or

[0220] represents cycloalkyl having 3 to 6 carbon atoms, wvhere each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, isopropyl and tert-butyl,

[0221] or

[0222] represents phenylalkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituenits from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

[0223] or

[0224] represents phenylalkenyl having 2 to 4 carbon atoms in the alkenyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,

[0225] or

[0226] represents phenoxyalkyl having 1 to 4 carbon atoms in the straight- chain or branched oxyalkyl moiety, where the phenyl moiety may be mono- to trisubstituted by identical or different substituents from the group consisting of lluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromctlioxy, trifluoromethyltliio, chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, mcthoximiinometiiyl, 1-methioximinoethyl, nitro and cyano,

[0227] or

[0228] represents plienyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trinfuoromethyl, trifluoromethoxy, trifluoromethylthio, chliorodifluoro-methoxy, difluoromethoxy, chlorodi fluoromethylthiio, methoxy-carbonyl, ethoxycarbonyl, methoximinomethyl, I-methoximinoethyl, nitro and cyano,

[0229] or

[0230] represents pyrazolyl, imidazolyl, 1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl or benzimidazolyl, which each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, chloroclifluoromcthoxy, clilorodifnuoromethylthio, hydroxymethyl, hydroxyethyl, hydroxyalkinyl having 4 to 6 carbon atoms, mcthoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano, formyl, dimethoxymethyl, acetyl and propioniyl.

[0231] R3 furthermore particularly preferably represents a radical of the formula

[0232] R9 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-btityl, sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, represents naphthyl or represents phenyl which may be mono- to tristibstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, phenyl, phienoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy. trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoro-methoxy and trifluoromethylthio, and

[0233] R10 particularly preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, dinluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio.

[0234] R3 furthermore particularly preferably represents a radical of the formula

[0235] R1 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or n-pentyl,

[0236] R12 par-ticularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, telt-butyl or n-pentyl,

[0237] X1 patiticularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, etioxy, phenyl, phenoxy, tricliloromethyl, trifluoromethyl, trifluorometlhoxy, difluorometioxy or trifluorometliyl and

[0238] m also particularly preferably represents the numbers 0, 1 or 2, where X1 may represent identical or different radicals if m represents 2

[0239] R3 furthermore particularly preferably r eprese nts a radical of the formula

[0240] in which

[0241] R13 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, ti-butyl, iso-bLutyl, scc-butyl, tert-buityl or ti-pentyl,

[0242] R 14 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-buityl, sec-butyl, tert-butyl or n-pentyl,

[0243] X2 particularly preferably represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromcthyl, trichloromethyl, difluoiomethyl, trichloromethoxy, trifluoromethioxy, difluoromethoxy, difluorochloromethoxy or phenyl,

[0244] n also particularly preferably represents the numbers 0 or 1 and

[0245] p also particularly preferably represents the numbers 0, 1 or 2, where X2 may represent identical or different radicals if p represents 2.

[0246] R3 furthermore particularly preferably represents a radical of the formula

[0247] in which

[0248] R15 particularly preferably represents the radical of the formula

[0249] in which

[0250] X3 particularly preferably represents fluorine, chlorine, bromine, methyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or phenyl and

[0251] q also particularly preferably represents the numbers 0, 1 or 2, 25 where X3 represents identical or different radicals if q represents 2,

[0252] R16 particularly preferably represents methyl, ethyl, n-propyl, n-butyl or represents the radical of the formula

[0253] in which

[0254] Y1 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, trichloromethiyl, trifluoromethiyl, tri-nuoromethoxy, difluoromethoxy or phenyl, and

[0255] r also particularly preferably represents the numbers 0, 1 or 2, where Y1 represents identical or different radicals if r represents 2, and

[0256] R17 particularly preferably represents methyl, ethyl, n-propyl or n-butyl. R3 furthermore particularly preferably represents a radical of the formula

[0257] ,in which

[0258] Rl8 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-bltyl, sec-butyl, iso-buityl, tert-btityl, halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, cyclopropyl, cyclopentyl or cyclohexyl, which is optionally mono- to irisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl, and also represents phenyl, benzyl or phenethyl, where each of the three last-mentioned radicals may be mono- to trisubstitllted in the phenyl moiety by identical or different substituients from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methioxy, methylthio, trichiloromethiyi, trifluoromiethyl, trinfuoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl and phenoxy.

[0259] R3 furthermore particularly preferably represents a radical of the formula

[0260] , in which

[0261] R19 particularly preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms or represents cyclopropyl, cyclopentyl or cyclohexyl, which is optionally mono- to trisubstitlited by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl and ethyl,

[0262] X4 particularly preferably represents fluorine, chlorine, bromine, methyl, mchoxy, mcthylthio, trichloromethyl, tri fluoromethyl, trifilltoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

[0263] s also particularly preferably represents the numbers 0, 1,2 or 3, where X4 represents identical or different radicals if s represents 2 or 3 and Y2 also particularly preferably represents an oxygen atom, a CH2 group or a direct bond.

[0264] R3 furthermore particularly preferably represents a radical of the formula

[0265] ,in which

[0266] R20 particularly preferably represents methyl, isopropyl, tert-butyl, fluoro- tert-butyl, difluoro-tert-butyl, represents cyclopropyl, cyclopentyl or cyclohexyl, which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, and methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety andl 1 or 2 carbon atoms in alkyl moiety, phenyl which is optionally mono- or disubstituted by identical or different substituentls from the group consisting of fluorine, chlorine and bromine, or represents benzyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine,

[0267] X5 particularly preferably represents fluorine, chlorine, bromine, nitro, methyl, ethyl, tert-butyl, methoxy, methyltlio, trichloromethyl, trifluoromethyl, trifIuoromethoxy, dinluoromethoxy, trifitioromethlylthio, phenyl or phenoxy,

[0268] 1 also particularly preferably represents the numbers 0,1,2 or 3, where X5 represents identical or different radicals if t represents 2 or 3 and

[0269] Y3 also particularly preferably represents an oxygen atom or represents a CH2 group.

[0270] R3 furthermore particularly preferably represents a radical of the formula

[0271] , in which

[0272] A particularly preferably represents alkanediyl having 2 or 3 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl and tert-butyl,

[0273] x6 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, mcthoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoro-methoxy, trifluoromethylthio, difluoromethoxy, phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl and/or represents phenoxy which is optionally mono- to trisubstitrited by identical or different substituents from the group consisting of fluorine, chlorine and methyl and

[0274] u also particularly preferably represents the numbers 0, l, 2 or 3, where X6 represents identical or different radicils if u represents 2 or 3.

[0275] R3 furthermore particularly preferably represents a radical of the formnula

[0276] , in which

[0277] R21 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, fluoroalkoxyalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine atoms in the fluoroalkoxy moiety and 1 or 2 carbon atoms in the alkyl moiety, represents cyclopropyl, cyclopentyl or cyclohexyl, which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine nd methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine or represents benzyl which is optionally mono- or disubstitrited by identical or different substituents from the group consisting of fluorine, chlorine and bromine,

[0278] X7 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy and

[0279] v also particularly preferably represents the numbers 0, 1, 2 or 3, where X7 represents identical or different radicals if v represents 2 or 3.

[0280] R3 furthermore particularly preferably represents a radical of the formula

[0281] in which

[0282] R22 particularly preferably represents methyl, isopropyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, represents cyclopropyl, cyclopentyl or cyclohexyl, which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, or represents benzyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, X8 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

[0283] Y4 also particularly preferably represents an oxygen atom or represents a CH2 group, and

[0284] w also particularly preferably represents the numbers 0, 1, 2 or 3, where X8 represents identical or different radicals if w represents 2 or 3.

[0285] R3 moreover also preferably represents a radical of the formula

[0286] in which

[0287] R23 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, trifluoromethoxy and difluoromethoxy or represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moiety which is optionally mono- or disubstituted in the phenyl moiety by identical or different substituents from the group consisting of fluorine, chlorine, bromine. methyl, ethyl, trifluomethyl, trichloromethyl, methoxy, ethoxy, trifluoromethyoxy and difluoromethoxy,

[0288] X9 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl or phenoxy, and

[0289] z also particularly preferably represents the numbers 0, 1, 2 or 3, where X9 represents identical or different radicals if z represents 2 or 3.

[0290] Q also particularly preferably represents sulphur.

[0291] Preferred compounds according to the invention are also addition products of salts of metals of main groups II to IV and subgroups I and II and IV to VIl of the Periodic Table of the Elements and those triazolinethione-phosphoric acid derivatives of the formula (I) in which R1, R2, R3 and Q each have those meanings which have been mentioned as being preferred for these substituents.

[0292] Particular preference is given here to salts of copper, zinc, manganese, magnesium, tin, iron and nickel. Suitable anions of these salts are those which are derived from acids which lead to physiologically acceptable addition products. Particularly preferred acids of this type are, in this context, the hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, furthermore phosphoric acid, nitric acid and sulphuric acid.

[0293] The triazolinethiones required as starting materials for preparing the substances according to the invention can be present in the “thiono” form of the formula

[0294] or in the tautomefic “mercapto” form of the formula

[0295] Thus, it is possible that the substances according to the invention are derived both from the “thiono” form of the formula (II) and from the “mercapto” form of the formula (IIa). This means that the substances according to the invention are present either as substances of the formula or of the formula

[0296] or as mixtures of substances of the formulae (I) and (Ia). For the sake of simplicity, only the structure of the “thiono” form is given in each case.

[0297] Examples of substances according to the invention which may be mentioned are the triazolinethione-phosphoric acid derivatives listed in the tables below.

1TABLE 1

R7R8R1R2′

—C(CH3)3—CH3—C2H5

—C(CH3)3—C2H5—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—O—CH3—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—NH—CH3—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—CH3—C2H5

—C(CH3)3—C2H5—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—OCH3—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—NH—CH3—C2H5

—C(CH3)3—CH3—C2H5

—C(CH3)3—C2H5—C2H5

—C(CH3)3

—C2H5

—C(CH3)3—NH—CH3—C2H5

—CH3—C2H5

—C2H5—C2H5

—C2H5

—NH—CH3—C2H5

—C4H9-n—CH3—C2H5

—C4H9-n—C2H5—C2H5

—C4H9-n

—C2H5

—C4H9-n—NH—CH3—C2H5

—CH3—C2H5

—OCH3—C2H5

100

—C2H5

101

102

—NH—CH3—C2H5

103

—C(CH3)3—CH3—C2H5

104

—C(CH3)3—OC2H5—C2H5

105

—C(CH3)3

106

—C2H5

107

—C(CH3)3—OCH3—C2H5Cl2CH—CCl2—CH2——C(CH3)3—OCH3—C2H5Cl2CH—CCl2—CH2——C(CH3)3—OC2H5—C2H5Cl2CH—CCl2—CH2—

108

—OCH3—C2H5Cl2CH—CCl2—CH2—

109

—OC2H5—C2H5Cl2CH—CCl2—CH2—

110

—OC3H7—C2H5Cl2CH—CCl2—CH2—

111

—OCH3—C2H5

112

—C(CH3)3—OCH3—C2H5

113

—C(CH3)3—OC2H5—C2H5

114

115

—OCH3—C2H5

116

117

—OC2H5—C2H5

118

119

—OC2H5—C2H5

120

121

—OC2H5—C2H5

122

123

—OCH(CH3)2—C2H5Cl2CH—CCl2—

124

—OCH(CH3)2—C2H5

125

—C(CH3)3—OCH(CH3)2—C2H5

126

—C(CH3)3—OC2H5—C2H5

127

—C(CH3)3

128

—C2H5

[0298]

2

TABLE 2

129

R9
R10
R1
R2′

130

131

—OC2H5
—C2H5

132

133

—OC2H5
—C2H5

134

135

—OC2H5
—C2H5

136

137

—OC2H5
—C2H5

138

139

—OC2H5
—C2H5

140

141

—OC2H5
—C2H5

142

143

—OC2H5
—C2H5

144

145

—OC2H5
—C2H5

146

147

—OC2H5
—C2H5

148

149

—OC2H5
—C2H5

150

151

—OC2H5
—C2H5

152

153

—OC2H5
—C2H5

154

155

—OC2H5
—C2H5

156

157

—OC2H5
—C2H5

158

159

—OC2H5
—C2H5

160

161

—OC2H5
—C2H5

162

163

—OC2H5
—C2H5

164

165

—OC2H5
—C2H5

166

167

—OC2H5
—C2H5

168

169

—OC2H5
—C2H5

170

171

—OC2H5
—C2H5

172

173

—OC2H5
—C2H5

174

175

—OC2H5
—C2H5

176

177

—OC2H5
—C2H5

178

179

—OC2H5
—C2H5

180

181

—OC2H5
—C2H5

182

183

—OC2H5
—C2H5

184

185

—OC2H5
—C2H5

186

187

—OC2H5
—C2H5

188

189

—OC2H5
—C2H5

190

191

—OC2H5
—C2H5

192

193

—OC2H5
—C2H5

194

195

—OC2H5
—C2H5

196

197

—OC2H5
—C2H5

198

199

—NH—CH3
—C2H5

200

201

—NH—CH3
—C2H5

202

203

—NH—CH3
—C2H5

204

205

—NH—CH3
—C2H5

206

207

—NH—CH3
—C2H5

208

209

—NH—CH3
—C2H5

210

211

—NH—CH3
—C2H5

212

213

—OC2H5
—C2H5

214

215

—OC2H5
—C2H5

216

217

—OC2H5
—C2H5

218

219

—OC2H5
—C2H5

220

221

—OC2H5
—C2H5

222

223

—OC2H5
—C2H5

224

225

—OC2H5
—C2H5

226

227

—OC2H5
—C2H5

—CH3

228

—OC2H5
—C2H5

—CH3

229

—OC2H5
—C2H5

—CH3

230

—OC2H5
—C2H5

—C(CH3)3

231

—OC2H5
—C2H5

232

233

—OC2H5
—C2H5

234

235

—C2H5
—C2H5

236

237

—C2H5
—C2H5

238

239

—C2H5
—C2H5

240

241

—C2H5
—C2H5

242

243

—C2H5
—C2H5

244

245

—C2H5
—C2H5

246

247

—C2H5
—C2H5

248

249

—C2H5
—C2H5

250

251

—C2H5
—C2H5

252

253

—C2H5
—C2H5

254

255

—C2H5
—C2H5

256

257

—C2H5
—C2H5

258

259

—C2H5
—C2H5

260

261

—C2H5
—C2H5

262

263

—C2H5
—C2H5

264

265

—C2H5
—C2H5

266

267

—C2H5
—C2H5

268

269

—C2H5
—C2H5

270

271

—C2H5
—C2H5

272

273

—C2H5
—C2H5

274

275

—C2H5
—C2H5

276

277

—C2H5
—C2H5

278

279

—C2H5
—C2H5

280

281

—C2H5
—C2H5

282

283

—C2H5
—C2H5

284

285

—C2H5
—C2H5

286

287

—C2H5
—C2H5

288

289

—C2H5
—C2H5

290

291

—C2H5
—C2H5

292

293

—C2H5
—C2H5

294

295

—C2H5
—C2H5

296

297

—C2H5
—C2H5

298

299

—C2H5
—C2H5

300

301

—C2H5
—C2H5

302

303

—C2H5
—C2H5

304

305

—C2H5
—C2H5

306

307

—C2H5
—C2H5

308

309

—C2H5
—C2H5

310

311

—C2H5
—C2H5

312

313

—C2H5
—C2H5

314

315

—C2H5
—C2H5

316

317

—C2H5
—C2H5

318

319

—C2H5
—C2H5

320

321

—C2H5
—C2H5

322

323

—C2H5
—C2H5

324

325

—C2H5
—C2H5

326

327

—C2H5
—C2H5

328

329

—C2H5
—C2H5

330

331

—C2H5
—C2H5

—CH3

332

—C2H5
—C2H5

—CH3

333

—C2H5
—C2H5

—CH3

334

—C2H5
—C2H5

—C(CH3)3

335

—C2H5
—C2H5

336

337

—C2H5
—C2H5

[0299]

3

TABLE 3

338

R11
R12
R1
R2′
X1m

—CH3
—CH3
—OC2H5
—C2H5
4-Br

—CH3
—CH3
—OC2H5
—C2H5
4-F

—CH3
—CH3
—OC2H5
—C2H5
2,4-Cl2

—CH3
H
—OC2H5
—C2H5
4-Cl

—CH3
—CH3
—OC2H5
—C2H5
—

—CH3
—CH3
—OC2H5
—C2H5
4-CH3

—CH3
—CH3
—OC2H5
—C2H5
2-F,4-Cl

—C2H5
H
—OC2H5
—C2H5
4-Cl

—C2H5
—C2H5
—OC2H5
—C2H5
4-Cl

—C3H7-n
H
—OC2H5
—C2H5
4-Cl

—C2H5
H
—OC2H5
—C2H5
2,4-Cl2

—C2H5
H
—OC2H5
—C2H5
4-F

—C2H5
H
—OC2H5
—C2H5
4-Br

—C2H5
H
—OC2H5
—C2H5

339

—C2H5
H
—OC2H5
—C2H5
4-C4H9-t

—C3H7-i
H
—OC2H5
—C2H5
4-Cl

—C5H11-n
H
—OC2H5
—C2H5
4-Cl

—CH3
—CH3
—OC2H5
—C2H5

340

—CH3
—CH3
—OC2H5
—C2H5
4-C4H9-t

—C4H9-n
H
—OC2H5
—C2H5
4-Cl

—C4H9-i
H
—OC2H5
—C2H5
4-Cl

—CH3
—C2H5
—OC2H5
—C2H5
4-Cl

—CH3
—CH3
—C2H5
—C2H5
4-Cl

—CH3
—CH3
—C2H5
—C2H5
4-Br

—CH3
—CH3
—C2H5
—C2H5
4-F

—CH3
—CH3
—C2H5
—C2H5
2,4-Cl2

—CH3
H
—C2H5
—C2H5
4-Cl

—CH3
—CH3
—C2H5
—C2H5
—

—CH3
—CH3
—C2H5
—C2H5
4-CH3

—CH3
—CH3
—C2H5
—C2H5
2-F, 4-Cl

—C2H5
H
—C2H5
—C2H5
4-Cl

—C2H5
—C2H5
—C2H5
—C2H5
4-Cl

—C3H7-n
H
—C2H5
—C2H5
4-Cl

—C2H5
H
—C2H5
—C2H5
2,4-Cl2

—C2H5
H
—C2H5
—C2H5
4-F

—C2H5
H
—C2H5
—C2H5
4-Br

—C2H5
H
—C2H5
—C2H5

341

—C2H5
H
—C2H5
—C2H5
4-C4H9-t

—C3H7-i
H
—C2H5
—C2H5
4-Cl

—C5H11-n
H
—C2H5
—C2H5
4-Cl

—CH3
—CH3
—C2H5
—C2H5

342

—CH3
—CH3
—C2H5
—C2H5
4-C4H9-t

—C4H9-n
H
—C2H5
—C2H5
4-Cl

—C4H9-i
H
—C2H5
—C2H5
4-Cl

—CH3
—C2H5
—C2H5
—C2H5
4-Cl

—CH3
—CH3
—OC2H5
—C2H5
2-Cl

—CH3
—CH3
—OC2H5
—C2H5
2,3-Cl2

—CH3
—CH3
—OC2H5
—C2H5
4-CF3

—CH3
—CH3
—OC2H5
—C2H5
4-OCF3

—CH3
—CH3
—OC2H5
—C2H5
4-Cl

[0300]

4

TABLE 4

343

R13
R14
R1
X2p
n
R2′

—CH3
—CH3
—OC2H5
4-Br
0
—C2H5

—CH3
—CH3
—OC2H5
4-F
0
—C2H5

—CH3
—CH3
—OC2H5
2,4-Cl2
0
—C2H5

—CH3
H
—OC2H5
4-Cl
0
—C2H5

—CH3
—CH3
—OC2H5
—
0
—C2H5

—CH3
—CH3
—OC2H5
4-CH3
0
—C2H5

—CH3
—CH3
—OC2H5
2-F, 4-Cl
0
—C2H5

—C2H5
H
—OC2H5
4-Cl
0
—C2H5

—C2H5
—C2H5
—OC2H5
4-Cl
0
—C2H5

—C3H7-n
H
—OC2H5
4-Cl
0
—C2H5

—C2H5
H
—OC2H5
2,4-Cl2
0
—C2H5

—C2H5
H
—OC2H5
4-F
0
—C2H5

—C2H5
H
—OC2H5
4-Br
0
—C2H5

—C2H5
H
—OC2H5
4-NO2
0
—C2H5

—C2H5
H
—OC2H5
4-C4H9-t
0
—C2H5

—C3H7-i
H
—OC2H5
4-Cl
0
—C2H5

—C5H11-n
H
—OC2H5
4-Cl
0
—C2H5

—CH3
—CH3
—OC2H5
4-CN
0
—C2H5

—CH3
—CH3
—OC2H5
4-C4H9-t
0
—C2H5

—C4H9-n
H
—OC2H5
4-Cl
0
—C2H5

—C4H9-i
H
—OC2H5
4-Cl
0
—C2H5

—CH3
—C2H5
—OC2H5
4-Cl
0
—C2H5

—CH3
—CH3
—C2H5
4-Cl
0
—C2H5

—CH3
—CH3
—C2H5
4-Br
0
—C2H5

—CH3
—CH3
—C2H5
4-F
0
—C2H5

—CH3
—CH3
—C2H5
2,4-Cl2
0
—C2H5

—CH3
H
—C2H5
4-Cl
0
—C2H5

—CH3
—CH3
—C2H5
—
0
—C2H5

—CH3
—CH3
—C2H5
4-CH3
0
—C2H5

—CH3
—CH3
—C2H5
2-F, 4-Cl
0
—C2H5

—C2H5
H
—C2H5
4-Cl
0
—C2H5

—C2H5
—C2H5
—C2H5
4-Cl
0
—C2H5

—C3H7-n
H
—C2H5
4-Cl
0
—C2H5

—C2H5
H
—C2H5
2,4-Cl2
0
—C2H5

—C2H5
H
—C2H5
4-F
0
—C2H5

—C2H5
H
—C2H5
4-Br
0
—C2H5

—C2H5
H
—C2H5
4-NO2
0
—C2H5

—C2H5
H
—C2H5
4-C4H9-t
0
—C2H5

—C3H7-i
H
—C2H5
4-Cl
0
—C2H5

—C5H11-n
H
—C2H5
4-Cl
0
—C2H5

—CH3
—CH3
—C2H5
4-CN
0
—C2H5

—CH3
—CH3
—C2H5
4-C4H9-t
0
—C2H5

—C4H9-n
H
—C2H5
4-Cl
0
—C2H5

—C4H9-i
H
—C2H5
4-Cl
0
—C2H5

—CH3
—C2H5
—C2H5
4-Cl
0
—C2H5

—CH3
—CH3
—OC2H5
4-OCH3
0
—C2H5

—CH3
—CH3
—OC2H5
2-OCH3
0
—C2H5

—CH3
—CH3
—OC2H5
2-CF3
0
—C2H5

—CH3
—CH3
—OC2H5
4-CF3
0
—C2H5

—CH3
—CH3
—OC2H5
2-OCF3
0
—C2H5

—CH3
—CH3
—OC2H5
2-OCHF2
0
—C2H5

—CH3
—CH3
—OC2H5
4-OCF3
0
—C2H5

—CH3
—CH3
—C2H5
4-OCH3
0
—C2H5

—CH3
—CH3
—C2H5
2-OCH3
0
—C2H5

—CH3
—CH3
—C2H5
2-CF3
0
—C2H5

—CH3
—CH3
—C2H5
4-CF3
0
—C2H5

—CH3
—CH3
—C2H5
2-OCF3
0
—C2H5

—CH3
—CH3
—C2H5
2-OCHF2
0
—C2H5

—CH3
—CH3
—C2H5
4-OCF3
0
—C2H5

—CH3
—CH3
—OC2H5
4-Br
1
—C2H5

—CH3
—CH3
—OC2H5
4-F
1
—C2H5

—CH3
—CH3
—OC2H5
2,4-Cl2
1
—C2H5

—CH3
H
—OC2H5
4-Cl
1
—C2H5

—CH3
—CH3
—OC2H5
—
1
—C2H5

—CH3
—CH3
—OC2H5
4-CH3
1
—C2H5

—CH3
—CH3
—OC2H5
2-F, 4-Cl
1
—C2H5

—C2H5
H
—OC2H5
4-Cl
1
—C2H5

—C2H5
—C2H5
—OC2H5
4-Cl
1
—C2H5

—C3H7-n
H
—OC2H5
4-Cl
1
—C2H5

—C2H5
H
—OC2H5
2,4-Cl2
1
—C2H5

—C2H5
H
—OC2H5
4-F
1
—C2H5

—C2H5
H
—OC2H5
4-Br
1
—C2H5

—C2H5
H
—OC2H5
4-NO2
1
—C2H5

—C2H5
H
—OC2H5
4-C4H9-t
1
—C2H5

—C3H7-i
H
—OC2H5
4-Cl
1
—C2H5

—C5H11-n
H
—OC2H5
4-Cl
1
—C2H5

—CH3
—CH3
—OC2H5
4-CN
1
—C2H5

—CH3
—CH3
—OC2H5
4-C4H9-t
1
—C2H5

—C4H9-n
H
—OC2H5
4-Cl
1
—C2H5

—CH3
—CH3
—OC2H5
4-Cl
1
—C2H5

—CH3
—CH3
—C2H5
4-Cl
1
—C2H5

—C4H9-i
H
—OC2H5
4-Cl
1
—C2H5

—CH3
—C2H5
—OC2H5
4-Cl
1
—C2H5

—CH3
—CH3
—C2H5
4-Cl
1
—C2H5

—CH3
—CH3
—C2H5
4-Br
1
—C2H5

—CH3
—CH3
—C2H5
4-F
1
—C2H5

—CH3
—CH3
—C2H5
2,4-Cl2
1
—C2H5

—CH3
H
—C2H5
4-Cl
1
—C2H5

—CH3
—CH3
—C2H5
—
1
—C2H5

—CH3
—CH3
—C2H5
4-CH3
1
—C2H5

—CH3
—CH3
—C2H5
2-F, 4-Cl
1
—C2H5

—C2H5
H
—C2H5
4-Cl
1
—C2H5

—C2H5
—C2H5
—C2H5
4-Cl
1
—C2H5

—C3H7-n
H
—C2H5
4-Cl
1
—C2H5

—C2H5
H
—C2H5
2,4-Cl2
1
—C2H5

—C2H5
H
—C2H5
4-F
1
—C2H5

—C2H5
H
—C2H5
4-Br
1
—C2H5

—C2H5
H
—C2H5
4-NO2
1
—C2H5

—C2H5
H
—C2H5
4-C4H9-t
1
—C2H5

—C3H7-i
H
—C2H5
4-Cl
1
—C2H5

—C5H11-n
H
—C2H5
4-Cl
1
—C2H5

—CH3
—CH3
—C2H5
4-CN
1
—C2H5

—CH3
—CH3
—C2H5
4-C4H9-t
1
—C2H5

—C4H9-n
H
—C2H5
4-Cl
1
—C2H5

—C4H9-i
H
—C2H5
4-Cl
1
—C2H5

—CH3
—C2H5
—C2H5
4-Cl
1
—C2H5

—CH3
—CH3
—OC2H5
4-OCH3
1
—C2H5

—CH3
—CH3
—OC2H5
2-OCH3
1
—C2H5

—CH3
—CH3
—OC2H5
2-CF3
1
—C2H5

—CH3
—CH3
—OC2H5
4-CF3
1
—C2H5

—CH3
—CH3
—OC2H5
2-OCF3
1
—C2H5

—CH3
—CH3
—OC2H5
2-OCHF2
1
—C2H5

—CH3
—CH3
—OC2H5
4-OCF3
1
—C2H5

—CH3
—CH3
—C2H5
4-OCH3
1
—C2H5

—CH3
—CH3
—C2H5
2-OCH3
1
—C2H5

—CH3
—CH3
—C2H5
2-CF3
1
—C2H5

—CH3
—CH3
—C2H5
4-CF3
1
—C2H5

—CH3
—CH3
—C2H5
2-OCF3
1
—C2H5

—CH3
—CH3
—C2H5
2-OCHF2
1
—C2H5

—CH3
—CH3
—C2H5
2-OCF3
1
—C2H5

—CH3
—CH3
—OC2H5
2-Cl
0
—C2H5

—CH3
—CH3
—OC2H5
2,3-Cl2
0
—C2H5

—CH3
—CH3
—OC2H5
2-Cl
1
—C2H5

—CH3
—CH3
—OC2H5
4-Cl
0
—C2H5

[0301]

5

TABLE 5

344

R15
R16
R17
R1
R2′

345

—CH3
—CH3
—OC2H5
—C2H5

346

—CH3
—CH3
—OC2H5
—C2H5

347

—CH3
—CH3
—OC2H5
—C2H5

348

—CH3
—CH3
—OC2H5
—C2H5

349

—CH3
—CH3
—OC2H5
—C2H5

350

—CH3
—CH3
—OC2H5
—C2H5

351

—C4H9-n
—CH3
—OC2H5
—C2H5

352

353

—CH3
—OC2H5
—C2H5

354

355

—CH3
—OC2H5
—C2H5

356

—CH3
—CH3
—OC2H5
—C2H5

357

—C4H9-n
—CH3
—OC2H5
—C2H5

358

359

—CH3
—OC2H5
—C2H5

360

361

—CH3
—OC2H5
—C2H5

362

363

—CH3
—OC2H5
—C2H5

364

365

—CH3
—OC2H5
—C2H5

366

—C4H9-n
—CH3
—OC2H5
—C2H5

367

—C4H9-n
—CH3
—OC2H5
—C2H5

368

369

—CH3
—OC2H5
—C2H5

370

—C4H9-n
—CH3
—OC2H5
—C2H5

371

372

—CH3
—OC2H5
—C2H5

373

—CH3
—CH3
—C2H5
—C2H5

374

—CH3
—CH3
—C2H5
—C2H5

375

—CH3
—CH3
—C2H5
—C2H5

376

—CH3
—CH3
—C2H5
—C2H5

377

—CH3
—CH3
—C2H5
—C2H5

378

—CH3
—CH3
—C2H5
—C2H5

379

—C4H9-n
—CH3
—C2H5
—C2H5

380

381

—CH3
—C2H5
—C2H5

382

383

—CH3
—C2H5
—C2H5

384

—CH3
—CH3
—C2H5
—C2H5

385

—C4H9-n
—CH3
—C2H5
—C2H5

386

387

—CH3
—C2H5
—C2H5

388

389

—CH3
—C2H5
—C2H5

390

391

—CH3
—C2H5
—C2H5

392

393

—CH3
—C2H5
—C2H5

394

—C4H9-n
—CH3
—C2H5
—C2H5

395

—C4H9-n
—CH3
—C2H5
—C2H5

396

397

—CH3
—C2H5
—C2H5

398

—C4H9-n
—CH3
—C2H5
—C2H5

399

400

—CH3
—C2H5
—C2H5

401

402

—CH3
—OC2H5
—C2H5

403

404

—CH3
—C2H5
—C2H5

405

406

—CH3
—NH—CH3
—OC2H5

[0302]

6

TABLE 6

407

R18
R1
R2′

408

—OC2H5
—C2H5

409

—OC2H5
—C2H5

410

—OC2H5
—C2H5

411

—OC2H5
—C2H5

412

—OC2H5
—C2H5

413

—OC2H5
—C2H5

414

—OC2H5
—C2H5

415

—OC2H5
—C2H5

416

—OC2H5
—C2H5

—C4H9-n
—OC2H5
—C2H5

—C(CH3)3
—OC2H5
—C2H5

—CH(CH3)2
—OC2H5
—C2H5

417

—OC2H5
—C2H5

418

—OC2H5
—C2H5

—CH2—CH(CH3)2
—OC2H5
—C2H5

419

—OC2H5
—C2H5

420

—OC2H5
—C2H5

421

—OC2H5
—C2H5

422

—OC2H5
—C2H5

423

—OC2H5
—C2H5

424

—OC2H5
—C2H5

425

—OC2H5
—C2H5

426

—OC2H5
—C2H5

427

—OC2H5
—C2H5

428

—OC2H5
—C2H5

429

—OC2H5
—C2H5

430

—OC2H5
—C2H5

431

—OC2H5
—C2H5

432

—OC2H5
—C2H5

433

—OC2H5
—C2H5

434

—OC2H5
—C2H5

435

—OC2H5
—C2H5

436

—OC2H5
—C2H5

437

—OC2H5
—C2H5

438

—OC2H5
—C2H5

439

—OC2H5
—C2H5

440

—OC2H5
—C2H5

441

—OC2H5
—C2H5

442

—OC2H5
—C2H5

443

—OC2H5
—C2H5

444

—C2H5
—C2H5

445

—C2H5
—C2H5

446

—C2H5
—C2H5

447

—C2H5
—C2H5

448

—C2H5
—C2H5

449

—C2H5
—C2H5

450

—C2H5
—C2H5

451

—C2H5
—C2H5

452

—C2H5
—C2H5

—C4H9-n
—C2H5
—C2H5

—C(CH3)3
—C2H5
—C2H5

—CH(CH3)2
—C2H5
—C2H5

453

—C2H5
—C2H5

454

—C2H5
—C2H5

—CH2—CH(CH3)2
—C2H5
—C2H5

455

—C2H5
—C2H5

456

—C2H5
—C2H5

457

—C2H5
—C2H5

458

—C2H5
—C2H5

459

—C2H5
—C2H5

460

—C2H5
—C2H5

461

—C2H5
—C2H5

462

—C2H5
—C2H5

463

—C2H5
—C2H5

464

—C2H5
—C2H5

465

—C2H5
—C2H5

466

—C2H5
—C2H5

467

—C2H5
—C2H5

468

—C2H5
—C2H5

469

—C2H5
—C2H5

470

—C2H5
—C2H5

471

—C2H5
—C2H5

472

—C2H5
—C2H5

473

—C2H5
—C2H5

474

—C2H5
—C2H5

475

—C2H5
—C2H5

476

—C2H5
—C2H5

477

—C2H5
—C2H5

478

—C2H5
—C2H5

479

—C2H5
—C2H5

480

—C2H5
—C2H5

481

—OC2H5
—C2H5

482

—NH—CH3
—C2H5

[0303]

7

TABLE 7

483

Xs4
Y2
R19
R1
R2′

4-Cl
CH2
H
—OC2H5
—C2H5

4-CF3
CH2
H
—OC2H5
—C2H5

4-OCF3
CH2
H
—OC2H5
—C2H5

2,4-Cl2
CH2
H
—OC2H5
—C2H5

4-CH3
CH2
H
—OC2H5
—C2H5

2-Cl
CH2
H
—OC2H5
—C2H5

2-F
CH2
H
—OC2H5
—C2H5

4-F
CH2
H
—OC2H5
—C2H5

2-OCHF2
CH2
H
—OC2H5
—C2H5

4-Cl
O
H
—OC2H5
—C2H5

4-CF3
O
H
—OC2H5
—C2H5

4-OCF3
O
H
—OC2H5
—C2H5

2,4-Cl2
O
H
—OC2H5
—C2H5

4-CH3
O
H
—OC2H5
—C2H5

2-Cl
O
H
—OC2H5
—C2H5

2-F
O
H
—OC2H5
—C2H5

4-F
O
H
—OC2H5
—C2H5

2-OCHF2
O
H
—OC2H5
—C2H5

4-Cl
—
H
—OC2H5
—C2H5

4-CF3
—
H
—OC2H4
—C2H5

4-OCF3
—
H
—OC2H5
—C2H5

2,4-Cl2
—
H
—OC2H5
—C2H5

4-CH3
—
H
—OC2H5
—C2H5

2-Cl
—
H
—OC2H5
—C2H5

2-F
—
H
—OC2H5
—C2H5

4-F
—
H
—OC2H5
—C2H5

2-OCHF2
—
H
—OC2H5
—C2H5

4-Cl
CH2
—CH3
—OC2H5
—C2H5

4-CF3
CH2
—CH3
—OC2H5
—C2H5

4-OCF3
CH2
—CH3
—OC2H5
—C2H5

2,4-Cl2
CH2
—CH3
—OC2H5
—C2H5

4-CH3
CH2
—CH3
—OC2H5
—C2H5

2-Cl
CH2
—CH3
—OC2H5
—C2H5

2-F
CH2
—CH3
—OC2H5
—C2H5

4-F
CH2
—CH3
—OC2H5
—C2H5

2-OCHF2
CH2
—CH3
—OC2H5
—C2H5

4-Cl
O
—CH3
—OC2H5
—C2H5

4-CF3
O
—CH3
—OC2H5
—C2H5

2,4-Cl2
O
—CH3
—OC2H5
—C2H5

4-OCF3
O
—CH3
—OC2H5
—C2H5

2-F
O
—CH3
—OC2H5
—C2H5

2-OCHF2
O
—CH3
—OC2H5
—C2H5

4-Cl
—
—CH3
—OC2H5
—C2H5

4-CF3
—
—CH3
—OC2H5
—C2H5

2,4-Cl2
—
—CH3
—OC2H5
—C2H5

4-OCF3
—
—CH3
—OC2H5
—C2H5

2-F
—
—CH3
—OC2H5
—C2H5

2-OCHF2
—
—CH3
—OC2H5
—C2H5

4-Cl
CH2
C4H9-n
—OC2H5
—C2H5

2,4-Cl2
CH2
—CH(CH3)2
—OC2H5
—C2H5

4-OCF3
CH2
—C(CH3)3
—OC2H5
—C2H5

4-Cl
CH2

484

—OC2H5
—C2H5

4-Cl
CH2

485

—OC2H5
—C2H5

4-Cl
CH2

486

—OC2H5
—C2H5

4-Cl
CH2

487

—OC2H5
—C2H5

2,4,6-Cl3
CH2
—CH3
—OC2H5
—C2H5

488

CH2
—CH3
—OC2H5
—C2H5

489

CH2
—CH3
—OC2H5
—C2H5

4-Cl
CH2
H
—C2H5
—C2H5

4-CF3
CH2
H
—C2H5
—C2H5

4-OCF3
CH2
H
—C2H5
—C2H5

2,4-Cl2
CH2
H
—C2H5
—C2H5

4-CH3
CH2
H
—C2H5
—C2H5

2-Cl
CH2
H
—C2H5
—C2H5

2-F
CH2
H
—C2H5
—C2H5

4-F
CH2
H
—C2H5
—C2H5

2-OCHF2
CH2
H
—C2H5
—C2H5

4-Cl
O
H
—C2H5
—C2H5

4-CF3
O
H
—C2H5
—C2H5

4-OCF3
O
H
—C2H5
—C2H5

2,4-Cl2
O
H
—C2H5
—C2H5

4-CH3
O
H
—C2H5
—C2H5

2-Cl
O
H
—C2H5
—C2H5

2-F
O
H
—C2H5
—C2H5

4-F
O
H
—C2H5
—C2H5

2-OCHF2
O
H
—C2H5
—C2H5

4-Cl
—
H
—C2H5
—C2H5

4-CF3
—
H
—C2H5
—C2H5

4-OCF3
—
H
—C2H5
—C2H5

2,4-Cl2
—
H
—C2H5
—C2H5

4-CH3
—
H
—C2H5
—C2H5

2-Cl
—
H
—C2H5
—C2H5

2-F
—
H
—C2H5
—C2H5

4-F
—
H
—C2H5
—C2H5

2-OCHF2
—
H
—C2H5
—C2H5

4-Cl
CH2
—CH3
—C2H5
—C2H5

4-CF3
CH2
—CH3
—C2H5
—C2H5

4-OCF3
CH2
—CH3
—C2H5
—C2H5

2,4-Cl2
CH2
—CH3
—C2H5
—C2H5

4-CH3
CH2
—CH3
—C2H5
—C2H5

2-Cl
CH2
—CH3
—C2H5
—C2H5

2-F
CH2
—CH2
—C2H5
—C2H5

4-F
CH2
—CH3
—C2H5
—C2H5

2-OCHF2
CH2
—CH3
—C2H5
—C2H5

4-Cl
O
—CH3
—C2H5
—C2H5

4-CF3
O
—CH3
—C2H5
—C2H5

2,4-Cl2
O
—CH3
—C2H5
—C2H5

4-OCF3
O
—CH3
—C2H5
—C2H5

2-F
O
—CH3
—C2H5
—C2H5

2-OCHF2
O
—CH3
—C2H5
—C2H5

4-Cl
—
—CH3
—C2H5
—C2H5

4-CF3
—
—CH3
—C2H5
—C2H5

2,4-Cl2
—
—CH3
—C2H5
—C2H5

4-OCF3
—
—CH3
—C2H5
—C2H5

2-F
—
—CH3
—C2H5
—C2H5

2-OCHF2
—
—CH3
—C2H5
—C2H5

4-Cl
CH2
C4H9-n
—C2H5
—C2H5

2,4-Cl2
CH2
—CH(CH3)2
—C2H5
—C2H5

4-OCF3
CH2
—C(CH3)3
—C2H5
—C2H5

4-Cl
CH2

490

—C2H5
—C2H5

4-Cl
CH2

491

—C2H5
—C2H5

4-Cl
CH2

492

—C2H5
—C2H5

4-Cl
CH2

493

—C2H5
—C2H5

2,4,6-Cl3
CH2
—CH3
—C2H5
—C2H5

494

CH2
—CH3
—C2H5
—C2H5

495

CH2
—CH3
—C2H5
—C2H5

4-OCF3
CH2
—CH3
—C2H5
—C2H5

[0304]

8

TABLE 8

496

Xt5
R20
R1
Y3
R2′

2,4-Cl2

497

—OC2H5
O
—C2H5

4-Cl

498

—OC2H5
O
—C2H5

4-Br
—C(CH3)3
—OC2H5
O
—C2H5

—
—C(CH3)3
—OC2H5
O
—C2H5

4-C(CH3)3
—C(CH3)3
—OC2H5
O
—C2H5

2-Cl
—C(CH3)3
—OC2H5
O
—C2H5

3-Cl
—C(CH3)3
—OC2H5
O
—C2H5

4-F
—C(CH3)3
—OC2H5
O
—C2H5

499

—C(CH3)3
—OC2H5
O
—C2H5

500

—C(CH3)3
—OC2H5
O
—C2H5

2,4-Cl2
—C(CH3)3
—OC2H5
O
—C2H5

2-CH3, 4-Cl
—C(CH3)3
—OC2H5
O
—C2H5

3,4-(CH3)2
—C(CH3)3
—OC2H5
O
—C2H5

2,4,5-Cl2
—C(CH3)3
—OC2H5
O
—C2H5

4-Cl
—CH3
—OC2H5
O
—C2H5

4-Cl

501

—OC2H5
O
—C2H5

4-CF3
—C(CH3)3
—OC2H5
O
—C2H5

4-OCF3
—C(CH3)3
—OC2H5
O
—C2H5

2-OCHF2
—C(CH3)3
—OC2H5
O
—C2H5

4-OCH3
—C(CH3)3
—OC2H5
O
—C2H5

2,4-Cl2

502

—C2H5
O
—C2H5

4-Cl

503

—C2H5
O
—C2H5

4-Br
—C(CH3)3
—C2H5
O
—C2H5

—
—C(CH3)3
—C2H5
O
—C2H5

4-C(CH3)3
—C(CH3)3
—C2H5
O
—C2H5

2-Cl
—C(CH3)3
—C2H5
O
—C2H5

3-Cl
—C(CH3)3
—C2H5
O
—C2H5

4-F
—C(CH3)3
—C2H5
O
—C2H5

504

—C(CH3)3
—C2H5
O
—C2H5

505

—C(CH3)3
—C2H5
O
—C2H5

2.4-Cl2
—C(CH3)3
—C2H5
O
—C2H5

2-CH3, 4-Cl
—C(CH3)3
—C2H5
O
—C2H5

3,4-(CH3)2
—C(CH3)3
—C2H5
O
—C2H5

2,4,5-Cl3
—C(CH3)3
—C2H5
O
—C2H5

4-Cl
—CH3
—C2H5
O
—C2H5

4-Cl

506

—C2H5
O
—C2H5

4-CF3
—C(CH3)3
—C2H5
O
—C2H5

4-OCF3
—C(CH3)3
—C2H5
O
—C2H5

2-OCHF2
—C(CH3)3
—C2H5
O
—C2H5

4-OCH3
—C(CH3)3
—C2H5
O
—C2H5

4-Cl

507

—OC2H5
O
—C2H5

4-Cl

508

—OC2H5
O
—C2H5

4-Cl

509

—C2H5
O
—C2H5

4-Cl

510

—C2H5
O
—C2H5

2,4-Cl2

511

—OC2H5
CH2
—C2H5

4-Cl

512

—OC2H5
CH2
—C2H5

4-Br
—C(CH3)3
—OC2H5
CH2
—C2H5

—
—C(CH3)3
—OC2H5
CH2
—C2H5

4-C(CH3)3
—C(CH3)3
—OC2H5
CH2
—C2H5

2-Cl
—C(CH3)3
—OC2H5
CH2
—C2H5

3-Cl
—C(CH3)3
—OC2H5
CH2
—C2H5

4-F
—C(CH3)3
—OC2H5
CH2
—C2H5

513

—C(CH3)3
—OC2H5
CH2
—C2H5

514

—C(CH3)3
—OC2H5
CH2
—C2H5

2,4-Cl2
—C(CH3)3
—OC2H5
CH2
—C2H5

2-CH3, 4-Cl
—C(CH3)3
—OC2H5
CH2
—C2H5

3,4-(CH3)2
—C(CH3)3
—OC2H5
CH2
—C2H5

2,4,5-Cl3
—C(CH3)3
—OC2H5
CH2
—C2H5

4-Cl
—CH3
—OC2H5
CH2
—C2H5

4-Cl

515

—OC2H5
CH2
—C2H5

4-CF3
—C(CH3)3
—OC2H5
CH2
—C2H5

4-OCF3
—C(CH3)3
—OC2H5
CH2
—C2H5

2-OCHF2
—C(CH3)3
—OC2H5
CH2
—C2H5

4-OCH3
—C(CH3)3
—OC2H5
CH2
—C2H5

2,4-Cl2

516

—C2H5
CH2
—C2H5

4-Cl

517

—C2H5
CH2
—C2H5

4-Br
—C(CH3)3
—C2H5
CH2
—C2H5

—
—C(CH3)3
—C2H5
CH2
—C2H5

4-C(CH3)3
—C(CH3)3
—C2H5
CH2
—C2H5

2-Cl
—C(CH3)3
—C2H5
CH2
—C2H5

3-Cl
—C(CH3)3
—C2H5
CH2
—C2H5

4-F
—C(CH3)3
—C2H5
CH2
—C2H5

518

—C(CH3)3
—C2H5
CH2
—C2H5

519

—C(CH3)3
—C2H5
CH2
—C2H5

2,4-Cl2
—C(CH3)3
—C2H5
CH2
—C2H5

2-CH3, 4-Cl
—C(CH3)3
—C2H5
CH2
—C2H5

3,4-(CH3)2
—C(CH3)3
—C2H5
CH2
—C2H5

2,4,5-Cl3
—C(CH3)3
—C2H5
CH2
—C2H5

4-Cl
—CH3
—C2H5
CH2
—C2H5

4-Cl

520

—C2H5
CH2
—C2H5

4-CF3
—C(CH3)3
—C2H5
CH2
—C2H5

4-OCF3
—C(CH3)3
—C2H5
CH2
—C2H5

2-OCHF2
—C(CH3)3
—C2H5
CH2
—C2H5

4-OCH3
—C(CH3)3
—C2H5
CH2
—C2H5

4-Cl

521

—OC2H5
CH2
—C2H5

4-Cl

522

—OC2H5
CH2
—C2H5

4-Cl

523

—C2H5
CH2
—C2H5

4-Cl

524

—C2H5
CH2
—C2H5

4-Cl
—C(CH3)3
—OC2H5
O
—C2H5

4-Cl
—C(CH3)3
—C2H5
O
—C2H5

4-Cl
—C(CH3)3
—NH—CH3
O
—C2H5

[0305]

9

TABLE 9

525

Xu6
A
R1
R2′

2,4-Cl2
—(CH2)3—
—OC2H5
—C2H5

2,4-Cl2
—(CH2)2
—OC2H5
—C2H5

4-Cl

526

—OC2H5
—C2H5

4-CF3

527

—OC2H5
—C2H5

528

—CH2—CH2
—OC2H5
—C2H5

529

530

—OC2H5
—C2H5

4-F

531

—OC2H5
—C2H5

4-OCF3

532

—OC2H5
—C2H5

2,4-F2

533

—OC2H5
—C2H5

2-OCHF2

534

—OC2H5
—C2H5

535

—(CH2)3
—OC2H5
—C2H5

2,4,6-Cl3

536

—OC2H5
—C2H5

—

537

—OC2H5
—C2H5

2,4-F2

538

—OC2H5
—C2H5

539

540

—OC2H5
—C2H5

2,4-Cl2

541

—OC2H5
—C2H5

542

543

—OC2H5
—C2H5

2,4-Cl2

544

—OC2H5
—C2H5

545

546

—OC2H5
—C2H5

2,4-Cl2

547

—OC2H5
—C2H5

2,4-Cl2
—(CH2)3—
—C2H5
—C2H5

2,4-Cl2
—(CH2)2
—C2H5
—C2H5

4-Cl

548

—C2H5
—C2H5

4-CF3

549

—C2H5
—C2H5

550

—CH2—CH2
—C2H5
—C2H5

551

552

—C2H5 —C2H5

4-F

553

—C2H5
—C2H5

4-OCF3

554

—C2H5
—C2H5

2,4-F2

555

—C2H5
—C2H5

2-OCHF2

556

—C2H5
—C2H5

557

—(CH2)3
—C2H5
—C2H5

2,4,6-Cl2

558

—C2H5
—C2H5

—

559

—C2H5
—C2H5

2,4-F2

560

—C2H5
—C2H5

561

562

—C2H5
—C2H5

2,4-Cl2

563

—C2H5
—C2H5

564

565

—C2H5
—C2H5

2,4-Cl2

566

—C2H5
—C2H5

567

568

—C2H5
—C2H5

2,4-Cl2

569

—C2H5
—C2H5

2,4-Cl2

570

—OC2H5
—C2H5

2,4-Cl2

571

—C2H5
—C2H5

2,4-Cl2

572

—NH—CH3
—C2H5

[0306]

10

TABLE 10

573

Xv7
R21
R1
R2′

2,4-Cl2
—CH3
—OC2H5
—C2H5

2,4-Cl2
—C2H5
—OC2H5
—C2H5

2,4-Cl2
—CH(CH3)2
—OC2H5
—C2H5

4-Cl
—C3H7-n
—OC2H5
—C2H5

2,4-Cl2
—C4H9-n
—OC2H5
—C2H5

2,4-Cl2

574

—OC2H5
—C2H5

2,4-Cl2
—C(CH3)3
—OC2H5
—C2H5

2-Cl
—C3H7-n
—OC2H5
—C2H5

2-OCF3
—C3H7-n
—OC2H5
—C2H5

4-CF3
—C3H7-n
—OC2H5
—C2H5

4-CH3
—C3H7-n
—OC2H5
—C2H5

2,4,6-Cl3
—C3H7-n
—OC2H5
—C2H5

2,4-Cl2

575

—OC2H5
—C2H5

4-F
—C3H7-n
—OC2H5
—C2H5

2,4-Cl2

576

—OC2H5
—C2H5

2,4-Cl2

577

—OC2H5
—C2H5

2,4-Cl2

578

—OC2H5
—C2H5

2,4-Cl2

579

—OC2H5
—C2H5

2,4-Cl2

580

—OC2H5
—C2H5

2,4-Cl2

581

—OC2H5
—C2H5

2,4-Cl2

582

—OC2H5
—C2H5

2,4-Cl2

583

—OC2H5
—C2H5

2,4-Cl2

584

—OC2H5
—C2H5

2,4-Cl2

585

—OC2H5
—C2H5

2,4-Cl2
—CH2—O—CF2—CHF2
—OC2H5
—C2H5

2,4-Cl2
—CH2—O—CF2—CH3
—OC2H5
—C2H5

4-Cl
—CH2—O—CF2—CHF2
—OC2H5
—C2H5

2,4-Cl2
—CH2—O—CF3
—OC2H5
—C2H5

4-F
—CH2—O—CF2—CHF2
—OC2H5
—C2H5

2-Cl
—CH2—O—CF2—CHF2
—OC2H5
—C2H5

2,4-Cl2
—CH3
—C2H5
—C2H5

2,4-Cl2
—C2H5
—C2H5
—C2H5

2,4-Cl2
—CH(CH3)2
—C2H5
—C2H5

4-Cl
—C3H7-n
—C2H5
—C2H5

2,4-Cl2
—C4H9-n
—C2H5
—C2H5

2,4-Cl2

586

—C2H5
—C2H5

2,4-Cl2
—C(CH3)3
—C2H5
—C2H5

2-Cl
—C3H7-n
—C2H5
—C2H5

2-OCF3
—C3F7-n
—C2H5
—C2H5

4-CF3
—C3F7-n
—C2H5
—C2H5

4-CH3
—C3H7-n
—C2H5
—C2H5

2,4,6-Cl3
—C3H7-n
—C2H5
—C2H5

2,4-Cl2

587

—C2H5
—C2H5

4-F
—C3H7-n
—C2H5
—C2H5

2,4-Cl2

588

—C2H5
—C2H5

2,4-Cl2

589

—C2H5
—C2H5

2,4-Cl2

590

—C2H5
—C2H5

2,4-Cl2

591

—C2H5
—C2H5

2,4-Cl2

592

—C2H5
—C2H5

2,4-Cl2

593

—C2H5
—C2H5

2,4-Cl2

594

—C2H5
—C2H5

2,4-Cl2

595

—C2H5
—C2H5

2,4-Cl2

596

—C2H5
—C2H5

2,4-Cl2

597

—C2H5
—C2H5

2,4-Cl2
—CH2—O—CF2—CHF2
—C2H5
—C2H5

2,4-Cl2
—CH2—O—CF2—CH3
—C2H5
—C2H5

4-Cl
—CH2—O—CF2—CHF2
—C2H5
—C2H5

2,4-Cl2
—CH2—O—CF3
—C2H5
—C2H5

4-F
—CH2—O—CF2—CHF2
—C2H5
—C2H5

2-Cl
—CH2—O—CF2—CHF2
—C2H5
—C2H5

2,4-Cl2
—CH2—CF3
—OC2H5
—C2H5

2,4-Cl2
—CH2—CF3
—OC2H5
—C2H5

2,4-Cl2
—C3H7-n
—OC2H5
—C2H5

2,4-Cl2
—C3H7-n
—C2H5
—C2H5

2,4-Cl2
—C3H7-n
—NH—CH3
—C2H5

[0307]

11

TABLE 11

598

Xw8
R22
R1
Y4
R2′

2,4-Cl2

599

—OC2H5 O
—C2H5

4-Cl

600

601

—C(CH3)3
—OC2H5
O
—C2H5

602

—C(CH3)3
—OC2H5
O
—C2H5

2,4-Cl2
—C(CH3)3
—OC2H5
O
—C2H5

2-CH3, 4-Cl
—C(CH3)3 —OC2H5
O
—C2H5

3,4-(CH3)2
—C(CH3)3
—OC2H5
O
—C2H5

2,4,5-Cl3
—C(CH3)3
—OC2H5
O
—C2H5

4-Cl
—CH3
—OC2H5
O
—C2H5

4-Cl

603

—OC2H5
O
—C2H5

4-CF3
—C(CH3)3
—OC2H5
O
—C2H5

4-OCF3
—C(CH3)3
—OC2H5
O
—C2H5

2-OCHF2
—C(CH3)3
—OC2H5
O
—C2H5

4-OCH3 —C(CH3)3
—OC2H5
O
—C2H5

2,4-Cl2

604

—C2H5
O
—C2H5

4-Cl

605

606

—C(CH3)3
—C2H5
O
—C2H5

607

—C(CH3)3
—C2H5
O
—C2H5

2,4-Cl2
—C(CH3)3
—C2H5
O
—C2H5

2-CH3, 4-Cl
—C(CH3)3
—C2H5
O
—C2H5

3,4-(CH3)2
—C(CH3)3
—C2H5
O
—C2H5

2,4,5-Cl3
—C(CH3)3
—C2H5
O
—C2H5

4-Cl
—CH3
—C2H5
O
—C2H5

4-Cl

608

—C2H5
O
—C2H5

4-CF3
—C(CH3)3
—C2H5
O
—C2H5

4-OCF3
—C(CH3)3
—C2H5
O
—C2H5

2-OCHF2
—C(CH3)3
—C2H5
O
—C2H5

4-OCH3
—C(CH3)3
—C2H5
O
—C2H5

4-Cl

609

—OC2H5
O
—C2H5

4-Cl

610

—OC2H5
O
—C2H5

4-Cl

611

—C2H5
O
—C2H5

4-Cl

612

—C2H5
O
—C2H5

2,4-Cl2

613

—OC2H5
CH2
—C2H5

4-Cl

614

615

—C(CH3)3
—OC2H5
CH2
—C2H5

616

617

—OC2H5
CH2
—C2H5

4-CF3
—C(CH3)3
—OC2H5
CH2
—C2H5

4-OCF3
—C(CH3)3
—OC2H5
CH2
—C2H5

2-OCHF2
—C(CH3)3
—OC2H5
CH2
—C2H5

4-OCH3
—C(CH3)3
—OC2H5
CH2
—C2H5

2,4-Cl2

618

—C2H5
CH2
—C2H5

4-Cl

619

620

—C(CH3)3
—C2H5
CH2
—C2H5

621

622

—C2H5
CH2
—C2H5

4-CF3
—C(CH3)3
—C2H5
CH2
—C2H5

4-OCF3
—C(CH3)3
—C2H5
CH2
—C2H5

2-OCHF2
—C(CH3)3
—C2H5
CH2
—C2H5

4-OCH3 —C(CH3)3
—C2H5
CH2 —C2H5

4-Cl

623

—OC2H5
CH2
—C2H5

4-Cl

624

—OC2H5
CH2
—C2H5

4-Cl

625

—C2H5
CH2
—C2H5

4-Cl

626

—C2H5
CH2
—C2H5

4-Cl
—C(CH3)3
—OC2H5
O
—C2H5

4-Cl
—C(CH3)3
—C2H5
O
—C2H5

4-Cl
—C(CH3)3
—NH—CH3
O
—C2H5

[0308]

12

TABLE 12

627

Xz9
R23
R1
R2′

4-Cl
—C4H9-n
—OC2H5
—C2H5

2-Cl
—C4H9-n
—OC2H5
—C2H5

2,4-Cl2
—C4H9-n
—OC2H5
—C2H5

4-Br
—C4H9-n
—OC2H5
—C2H5

4-F
—C4H9-n
—OC2H5
—C2H5

4-C(CH3)3
—C4H9-n
—OC2H5
—C2H5

628

—C4H9-n
—OC2H5
—C2H5

4-Cl
—C(CH3)3
—OC2H5
—C2H5

2-Cl
—C(CH3)3
—OC2H5
—C2H5

2,4-Cl2
—C(CH3)3
—OC2H5
—C2H5

2,4,6-Cl3
—C(CH3)3 —OC2H5
—C2H5

4-CF3
—C(CH3)3 —OC2H5
—C2H5

2-OCHF2
—C(CH3)3
—OC2H5
—C2H5

4-Cl

629

—OC2H5
—C2H5

4-Cl

630

—OC2H5
—C2H5

4-Cl

631

—OC2H5
—C2H5

4-Cl

632

—OC2H5
—C2H5

4-Cl

633

—OC2H5
—C2H5

4-Cl

634

—OC2H5
—C2H5

—

635

—OC2H5
—C2H5

4-Cl
—C4H9-n
—C2H5
—C2H5

2-Cl
—C4H9-n
—C2H5
—C2H5

2,4-Cl2
—C4H9-n
—C2H5
—C2H5

4-Br
—C4H9-n
—C2H5
—C2H5

4-F
—C4H9-n
—C2H5
—C2H5

4-C(CH3)3
—C4H9-n
—C2H5
—C2H5

636

—C4H9-n
—C2H5
—C2H5

4-Cl
—C(CH3)3
—C2H5
—C2H5

2-Cl
—C(CH3)3
—C2H5
—C2H5

2,4-Cl2 —C(CH3)3
—C2H5
—C2H5

2,4,6-Cl3
—C(CH3)3
—C2H5
—C2H5

4-CF3
—C(CH3)3
—C2H5
—C2H5

2-OCHF2
—C(CH3)3
—C2H5
—C2H5

4-Cl

637

—C2H5
—C2H5

4-Cl

638

—C2H5
—C2H5

4-Cl

639

—C2H5
—C2H5

4-Cl

640

—C2H5
—C2H5

4-Cl

641

—C2H5
—C2H5

4-Cl

642

—C2H5
—C2H5

—

643

—C2H5
—C2H5

—

644

—C2H5
—C2H5

—

645

—OC2H5
—C2H5

—

646

—NH—CH3
—C2H5

[0309] Using 2-(1 -chloro-cyclopropyl)- 1-(2-chlorophenyl)-3-(4,5-dihydro-5-thiono-1,2,4-triazol-1-yl)-propan-2-ol and diethyl chloro-thiophosphate as starting materials, the course of the process according to thie invention can be illustrated by the formula scheme below.

647

[0310] The formula (II) provides a general definition of the triazolinethiones required as starting materials for carrying out the process according to the invention. In this formula, R3 preferably has those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for this radical.

[0311] The triazolinethiones of the formula (II) are known or can be prepared by known methods (cf. WO 96-16 048, DE-A-195 20 097, DE-A-195 20 098, DE-A-195 20 096, DE-A-195 20 095, DE-A-195 20 597, DE-A-195 20 593, DE-A-195 20 030, DE-A-195 21 487, DE-A-195 28 300, DE-A-195 29 091 and DE-A-195 29 089).

[0312] The formula (III) provides a general definition of the phosphoric acid derivatives required as reaction components for carrying out the process according to the invention. In this formula, R1, R2 and Q each preferably have those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these radicals.

[0313] The phosphoric acid derivatives of the formula (III) arc known or can be prepared by knovn methods.

[0314] Suitahle acid binders for cairying out the process according to the invention are all customary inorganic or organic bases. Preference is given to using alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide. sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

[0315] Suitable diluents for carrying out the process according to the invention are all inert organic solvents. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; esters, such as methyl acetate or ethyl acetate.

[0316] When carrying out the process according to the invention, the reaction temperatures can be varied within a certain range. In general, the process is carried out at temperatures between −20° C. and +40° C., preferably between −10° C. and +30° C.

[0317] The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

[0318] The process according to the invention can also be carried out under an atmosphere of protective gas. Preferred protective gases are nitrogen and argon.

[0319] When carrying out the process according to the invention, generally 1 to 3 mol of phosphoric acid derivative of the formula (III) and an equivalent amount or else an excess of acid binder are employed per mole of triazolinethione of the formula (II). Work-up is carried out by customary methods. In general, the reaction mixture is concentrated, the residue is mixed with water, the resulting mixture is extracted with an organic solvent which is sparingly miscible with water and the combined organic phases are dried and concentrated. The resulting product can, if appropriate, be freed of any impurities which are still present using customary methods, for example recrystallization or chromatography.

[0320] The triazolinethione-phosphoric acid derivatives of the formula (I) obtainable by the process according to the invention can be converted into metal salt complexes.

[0321] Suitable salts for the preparation of metal salt complexes of the compounds of the formula (I) are preferably those of metals which have already been mentioned in connection with the description of the metal salt complexes according to the invention as being preferred metal salts.

[0322] The metal salt complexes of the compounds of the formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol, and adding the solution to compounds of the formula (I). Metal salt complexes can be isolated in a known manner, for example by filtering off, and, if appropnate, purified by recrystallization.

[0323] The compounds according to the invention have a potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

[0324] Fungicides are employed in crop protection for controlling Plasmodioploromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

[0325] Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

[0326] Some pathogens causing fungal and bacterial diseases which come under the generic names listed above are mentioned as examples, but not by way of limitation:

[0327] Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae;

[0328] Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans;

[0329] Erwinia species, such as, for example, Erwinia amylovora;

[0330] Pythium species, such as, for example, Pythium ultimum;

[0331] Phytophthora species, such as, for example, Phytophthora infestans;

[0332] Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;

[0333] Plasmopara species, such as, for example, Plasmopara viticola;

[0334] Bremia species, such as, for example, Bremia lactucac;

[0335] Peronospora species, such as, for example, Peronospora pisi or P. brassicae;

[0336] Erysiphe species, such as, for example, Erysiphe graminis;

[0337] Sphaerotheca species, such as, for example, Spilaerotheca fuliginea;

[0338] Podospilaera species, such as, for example, Podosphaera leucotricha;

[0339] Venturia species, such as, for example, Venturia inaecqualis;

[0340] Pyreilophora species, such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, syn: llelminthospornum);

[0341] Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: lielminthospotium);

[0342] Uromyces species, such as, for example, Uromyces appendiculatus;

[0343] Puccinia species, such as, for exainple, Puccinia recondite:

[0344] Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

[0345] Tilletia species, such as, for example, Tilletia caries;

[0346] Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

[0347] Pellicularia species, such as, for example, Pellicularia sasakii;

[0348] Pyricularia species, such as, for example. Pyricularia oryzae;

[0349] Fusarium species, such as, for example, Fusarium culmorum:

[0350] Botrytis species, such as. for example, Botrytis cinerea;

[0351] Septoria species, such as, for example, Septoria nodorini;

[0352] Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

[0353] Cercospora species, such as, for example, Cercospora canescens:

[0354] Attenaria species, such as, for example, Altemaria brassicae; and

[0355] Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

[0356] The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil.

[0357] The active compounds according to the invention can be employed in particular for controlling Pyricularia oryzae in rice and for controlling cereal diseases, such as Puccinia, Erysiphe and Fusarium species. Furthermore, the compounds according to the invention can be used very successfully against Venturia, Podosphaera and Spaerotheca. They also have very good in vitro action.

[0358] Fuithermore, the active compounds according to the invention may also be employed to increase the yield of crops. They are also of low toxicity and are well tolerated by plants.

[0359] In the protection of materials, the compounds according to the invention can be employed for protecting industrial materials aigainst infection with, and destruction by, undesired microorganisms.

[0360] Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry. For example, industrial materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be adhesives, sizes, paper and board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with, or destroyed by, microorganisms. Parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms, may also he mentioned within the scope of the materials to be protected. Industrial materials which may be mentioned within the scope of the present invention are preferably adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat-transfer liquids.

[0361] Microorganisms capable of degrading or changing the industrial materials which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

[0362] Microorganisms of the following genera may be mentioned as examples:

[0363] Alternaria, such as Altemaria tenuis,

[0364] Aspergillus, such as Aspergillus niger,

[0365] Chaetomium, such as Chaetomium globosum,

[0366] Coniophora, such as Coniophora puetana,

[0367] Lentinus, such as Lentinus tigrinus,

[0368] Penicillium, such as Penicillium glaucum,

[0369] Polyporus, such as Polyporus versicolor,

[0370] Aureobasidium, such as Aureobasidium pullulans,

[0371] Sclerophomai, such as Scierophoma pityophila,

[0372] Triclioderma, such as Trichoderma viride,

[0373] Escherichia, such as Escherichia coli,

[0374] Pseudomiionias, such as Pseudomonas aerugillosa, and

[0375] Staphylococcus, such as Staphylococcus aureus.

[0376] Depending on their particular physical and/or chemical properties, the active compounds can be converted into the customary formulations. such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.

[0377] These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are mainly suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes. chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformrnmide or dimethyl sulphoxide, or else water.

[0378] Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatoraceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates. Suitable solid carriers for granules are, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite. or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are, for example, lignin-sulphite waste liquors and methylcellulose.

[0379] Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

[0380] It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizann dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0381] The fonnulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

[0382] The active compounds according to the invention can be used as such or in their formulations, also mixed with known fungicides, bactericides, acaricides, nematicides or insecticides in order thus, for example, to widen the spectrum of action or to prevent development of resistance. In many cases, synergistic effects are achieved, i.e. tlhe activity of the mixture exceeds the activity of the individual components.

[0383] Examnples of co-components in mixtures are the following compounds:

[0384] Fungicides:

[0385] aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilla.zine, azaconazole. azoxystrobin,

[0386] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl, bialaphos, binapacryl, bilphenyl, bitertanol, blasticidin-S, bromuconazole. bupirimate, buthiobate,

[0387] calcium polysulphiide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0388] debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0389] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole. famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, firametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,

[0390] guazatine, hexachlorobenzene, hexaconazole, hymexazole,

[0391] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminocladine triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, isovaledione,

[0392] kasugamycin, kresoxim-methyl, copper preparations, such as copper hydroxide, copper naphtheneate, copper oxychloride,copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0393] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0394] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0395] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

[0396] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

[0397] quinconazole, quintozene(PCNB),

[0398] sulphur and sulphur preparations,

[0399] tebuconazole, techloftalam, tecnazene, tetcyclasis, tetraconazole, thiabendazole, thicyofen, thifluzamides, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,

[0400] uniconazole,

[0401] validamycin A, vinclozolin, viniconazole,

[0402] zarilamide, zineb, ziram and also

[0403] Dagger G,

[0404] OK-8705,

[0405] OK-8801,

[0406] α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0407] α-(2,4-dichlorophenyl)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

[0408] α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

[0409] α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0410] (5RS,6RS)-6-hydroxy-2,2,7,7,-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0411] (E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0412] isopropyl {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl]-carbamate,

[0413] 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

[0414] 1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

[0415] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

[0416] 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

[0417] 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-1H-imidazole,

[0418] 1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0419] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0420] 2′,6-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5- carboxanilide,

[0421] 2.2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

[0422] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0423] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0424] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0425] 2-(2,3,3,-triodo-2-propenyl)-2H-tetrazole,

[0426] 2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0427] 2-[[6-deoxy-=b 4-O-(=b 4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d)pyrimidine-5-carbonitrile,

[0428] 2-aminobutane,

[0429] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0430] 2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0431] 2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0432] 2-phenylphenol(OPP),

[0433] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

[0434] 3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

[0435] 3-(1,1-dimethylpropyl-1-oxo-1H-indene-2carbonitrile,

[0436] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0437] 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0438] 4-methyl-tetrazolo[1,5-a]quinazolin-594H)-one,

[0439] 8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4,5]decane-2-methanamine,

[0440] 8-hydroxyquinoline sulphate,

[0441] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0442] bis-(1-methylethyl)-3-methyl--[(3-methylbenzoyl)oxy]-2,5-thiophenedicarboxylate,

[0443] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0444] cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methypropyl]-2,6-dimethyl-morpholinehydrochloride,

[0445] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0446] potassium hydrogen carbonate,

[0447] methanetetrathiol sodium salt,

[0448] methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0449] methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0450] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0451] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.

[0452] N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0453] N-(=b 2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0454] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0455] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0456] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0457] N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0458] N_(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

[0459] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0460] N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanemidamide,

[0461] N-formyl-N-hydroxy-DL-alanine-sodium salt,

[0462] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0463] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0464] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0465] spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

[0466] Bactericides

[0467] bromopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furanecarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

[0468] Insecticides/Acaricides/Nematicides

[0469] abamectin, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin, Bacillus thuringiensis, 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,

[0470] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, N-[(6-chloro-3-pyridinyl)-methyl]-N′-cyano-N-methyl-ethanimidamides, chlorpyrifos, chlorpyrifosM, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0471] deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

[0472] edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos,

[0473] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox,

[0474] imadacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda-cyhalothrin, lufenuron,

[0475] malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,

[0476] naled, NC 184, nitenpyram,

[0477] omethoate, oxamyl, oxydemethon M, oxydeprofos,

[0478] parathion A, parathion M, permethrin, phenothoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A. Profenophos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyriadaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos,

[0479] salithion, sebufos, silafluofen, sulfotep, sulprofos,

[0480] tebufenozide, tebufenpyrad, tebuprimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,

[0481] vamidothion, XMC, xylylcarb, zetamethrin.

[0482] It is also possible to admix other known active compounds, such as herbicides, fertilizers and growth-promoting substances.

[0483] The active compounds can be used as such or in the form of their commercial formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, spreading, dusting, foaming, brushing on and the like. It is further possible to apply the active compounds by the ultra-low volume method or to inject the active compound formulation, or the active compound itself, into the soil. The seed of the plants can also be treated.

[0484] When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the application rates of active compound are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seed, the application rates of active compound are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active compound are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.

[0485] The compositions used for protecting industrial materials generally comprise an amount of 1 to 95% by weight, preferably 10 to 75% by weight, of the active compounds.

[0486] The use concentrations of the active compounds according to the invention depend on the species and the occurrence of the microorganisms to the controlled and on the composition of the material to be protected. The optimum rate of application can be determined by test series. In general, the use concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.

[0487] The activity and the activity spectrum of the active compounds to be used according to the invention in the protection of materials and of the compositions, concentrates or quite generally formulations preparable from them can be increased by adding, if appropriate, other antimicrobially active compounds, fungicides, bactericides, herbicides, insecticides or other active compounds for increasing the activity spectrum or achieving particular effects, such as, for example, additional protection against insects. These mixtures may have a broader activity spectrum than the compounds according to the invention.

[0488] The preparation and the use of active compounds according to the invention are illustrated by the examples below.

PREPARATION EXAMPLES

Example 1

[0489]

648

[0490] Under an atmosphere of argon and with stirring at room temperature, a solution of 3.45 g (0.02 mol) of diethyl chlorothiophosphate in 40 ml of absolute acetonitrile is slowly added dropwise to a mixture of 6.88 g (0.02 mol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(4,5-dihydro-5-thiono-1,2,4-triazol-1-yl)-propan-2-ol, 5.52 g (0.04 mol) of dried and ground potassium carbonate, a few drops of diazabicyclooctane (DABCO) and 60 ml of absolute acetonitrile. After the addition has ended, the reaction mixture is stirred at room temperature for another 16 hours and then concentrated under reduced pressure. The residue that remains is stirred with 100 ml of water and the resulting mixture is extracted three times with 75 ml of methylene chloride each time. THe combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. This gives 3.17 g of a product which, according to HPLC analysis, comprises 82% of 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-[4,5-dihydro-5-thiono-4-(O,O-diethylthiophosphonyl)-1,2,4-triazol-1-yl]-propan-2-ol. Thus, the calculated yield is 63.8% of theory.

[0491] NMR spectrum (CDCl3, 162 MHz):

[0492]

31
Pδ=55.4 ppm

[0493] The substances listed in Tables 13 and 14 below are also prepared by the methods mentioned above.

13TABLE 13

649

Ex.No.R7R8R1R2′Physical const.2

650

651

652

—C2H5δ = 55.7 ppm*)3

653

654

655

—C2H5δ = 53.6 ppm*)4

656

657

658

—C2H5δ = 56.1 ppm*)5

659

660

—CH3

661

δ = 80.4 ppm*)6

662

663

—C2H5—C2H5δ = 91.3 ppm*)7

664

665

—NH—CH3—C2H5δ = 63.7 ppm*)8

666

667

668

669

δ = 68.2 ppm*)9

670

671

672

—C2H5δ = 51.2 ppm*)*)In each case, the signal in the 31P NMR spectrum (162 MHz, CDCl3) is stated.

[0494]

14

TABLE 14

673

Ex.

No.
R7
R8
R1
R2′
Physical const.

10

674

675

—OC2H5
—C2H5
δ = 55.4 ppm*)

11

676

677

—OC2H5
—C2H5
δ = 55.4 ppm*)

*)In each case, the signal in the 31P NMR spectrum (162 MHz, CDCl3) is stated.

USE EXAMPLES

Example A

Podosphaera Test (Apple)/Protective

[0495] Solvent: 47 parts by weight of acetone

[0496] Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

[0497] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0498] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causative organism of apple mildew Podosphaera leucotricha. The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.

[0499] Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0500] Active compounds, application rates and test results are shown in the table below.

15TABLE APodosphaera test (apple)/protectiveApplication rateof activecompound inActive compoundg/haEfficacy in %According to the invention:

678

5094(1)

679

5095(2)

680

5090(3)

681

50100 (4)

Example B

Sphaerotheca Test (Cucumber)/Protective

[0501] Solvent: 47 parts by weight of acetone

[0502] Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

[0503] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0504] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca filiginea. The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.

[0505] Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0506] Active compounds, application rates and test results are shown in the table below.

16TABLE BSphaerotheca test (cucumber)/protectiveApplication rateof activecompound inActive compoundg/haEfficacy in %According to the invention:

682

5093(1)

683

5095(4)

Example C

Venturia Test (Apple)/Protective

[0507] Solvent: 47 parts by weight of acetone

[0508] Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

[0509] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0510] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causative organism of apple scab Venturia inaequalis and then remain in an incubation cabin at approximately 20° C. and 100% relative atmospheric humidity for 1 day.

[0511] The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

[0512] Evaluation is carried out 12 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0513] Active compounds, application rates and test results are shown in the table below.

17TABLE CVenturia test (apple)/protectiveApplication rateof activecompound inActive compoundg/haEfficacy in %According to the invention:

684

5099(1)

685

5089(2)

686

5091(3)

687

5086(4)

Example D

Erysiphe Test (Barley)/Curative

[0514] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0515] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0516] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0517] To test for curative activity, young plants are dusted with spores of Erysiphe graminis f.sp. hordei. 48 hours after the inoculation, the plants are sprayed with the preparation of active compound at the stated application rate.

[0518] The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0519] Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0520] Active compounds, application rates and test results are shown in the table below.

18TABLE DErysiphe test (barley)/curativeApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

688

250 100

Example E

Erysiphe Test (Barley)/Protective

[0521] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0522] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0523] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0524] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate.

[0525] After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. hordei.

[0526] The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0527] Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0528] Active compounds, application rates and test results are shown in the table below.

19TABLE EErysiphe test (barley)/protectiveApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

689

250100

690

250100

691

250100

692

250100

693

250100

Example F

Erysiphe Test (Wheat)/Curitive

[0529] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0530] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0531] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0532] To test for curative activity, young plants are dusted with spores of Erysiphe graminis f.sp. tritici. 48 hours after the inoculation, the plants are sprayed with the preparation of active compound at the stated application rate.

[0533] The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0534] Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0535] Active compounds, application rates and test results are shown in the table below.

20TABLE FErysiphe test (wheat)/curativeApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

694

250100

Example G

Erysiphe Test (Wheat)/Protective

[0536] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0537] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0538] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0539] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate.

[0540] After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. tritici.

[0541] The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0542] Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0543] Active compounds, application rates and test results are shown in the table below.

21TABLE GErysiphe test (wheat)/protectiveApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

695

250100

Example H

Fusarium nivale
(Var. nivale) Test (Wheat)/Protective

[0544] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0545] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0546] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0547] To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Fusarium nivale (var. nivale).

[0548] The plants are placed in a greenhouse under transparent incubation hoods at a temperature of approximately 15° C. and a relative atmospheric humidity of approximately 100%.

[0549] Evaluation is carried out 4 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0550] Active compounds, application rates and test results are shown in the table below.

22TABLE HFusarium nivale (var. nivale) test (wheat)/protectiveApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

696

250100

Example I

Puccinia test (wheat)/curative

[0551] Solvent: 25 parts by weight of N,N-dimethylacetamide

[0552] Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

[0553] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier. and the concentrate is diluted with water to the desired concentration.

[0554] To test for curative activity, young plants are sprayed with a conidia suspension of Puccinia recondite. The plants remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 48 hours. The plants are then sprayed with the preparation of active compound at the stated application rate.

[0555] The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of rust pustules.

[0556] Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

[0557] Active compounds, application rates and test results are shown in the table below.

23TABLE IPuccinia test (wheat)/curativeApplicationrate of activecompound inActive compoundg/haEfficacy in %According to the invention:

697

250100

698

250100

699

250100

700

250100

701

250100

	Number	Date	Country
Parent	09859779	May 2001	US
Child	10003374	Nov 2001	US
Parent	09463270	Jan 2000	US
Child	09859779	May 2001	US

Triazolinethione-phosphoric acid derivatives

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Abstract

Description

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Priority Claims (1)

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