Substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones

A compound of the formula (I)

• in which
• Q1 represents oxygen or sulphur,
• Q2 represents oxygen or sulphur,
• R1 represents (i) hydrogen, cyano, or amino;
• (ii) an alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, or alkoxycarbonyl group, each of which groups has 1 to 6 carbon atoms in the alkyl moiety and each of which groups is optionally cyano-, halogen- or C1-C4-alkoxy-substituted;
• (iii) an alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynylcarbonyl, or alkynyloxycarbonyl group, each of which groups has 2 to 6 carbon atoms in the alkenyl or alkynyl moiety and each of which groups is optionally halogen-substituted;
• or (iv) a cycloalkyl or cycloalkylalkyl group, each of which groups has 3 to 6 carbon atoms in the cycloalkyl moiety and optionally has 1 to 4 carbon atoms in the alkyl moiety and each of which groups is optionally cyano-, halogen-, or C1-C4-alkyl-substituted,
• R2 represents (i) hydrogen, halogen, nitro, carboxyl, cyano, thiocarbamoyl, or amino;
• (ii) an alkyl, alkoxy, alkylthio, alkylamino, or dialkylamino group, each of which groups has 1 to 6 carbon atoms in the alkyl moiety and each of which groups is optionally cyano-, halogen-, or C1-C4-alkoxy-substituted;
• (iii) an alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy, or alkynylthio group, each of which groups has 2 to 6 carbon atoms in the alkenyl or alkynyl moiety and each of which groups is optionally halogen-substituted;
• or (iv) a cycloalkyl or cycloalkylalkyl group, each of which groups has 3 to 6 carbon atoms in the cycloalkyl moiety and optionally has 1 to 6 carbon atoms in the alkyl moiety and each of which groups is optionally cyano-, halogen- or C1-C4-alkyl-substituted,
• R3 represents hydrogen, cyano, or halogen,
• R4 represents cyano or thiocarbamoyl,
• R5 represents (i) hydrogen;
• (ii) alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety;
• or (iii) one of the radicals —R7, —O—R7, —SR7, —NH—R7, or —NR7R8,
• R6 represents (i) amino or hydroxyl or (ii) one of the radicals —R7 or —NR7R8,
• R7 represents (i) a straight-chain or branched alkyl that has 1 to 10 carbon atoms and is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of cyano;
• carboxyl;
• carbamoyl;
• thiocarbamoyl;
• halogen;
• an alkoxy, alkoxyalkoxy, alkylcarbonyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl trialkylsilyl, or alkylsulphonylaminocarbonyl group, each of which groups is straight-chain or branched and has 1 to 6 carbon atoms in the individual alkyl moieties;
• or heterocyclyl, where the heterocyclyl radical is a furyl, furylmethyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrrolidinyl, piperidinyl, morpholinyl, or chromanyl group;
• (ii) an alkenyl or alkynyl group, each of which groups has 2 to 8 carbon atoms and is optionally mono- or polysubstituted by identical or different halogens;
• (iii) a cycloalkyl or cycloalkylalkyl group, each of which groups has 3 to 7 carbon atoms in the cycloalkyl moiety and optionally 1 to 4 carbon atoms in the alkyl moiety and each of which groups is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of cyano, halogen, and C1-C4-alkyl;
• or (iv) an aryl, bis-aryl-alkyl, arylalkenyl, arylalkyl, aryloxyalkyl, or arylalkoxyalkyl group, each of which groups has 6 to 10 carbon atoms in the aryl moiety and optionally up to 4 carbon atoms in the alkyl moiety or alkenyl moiety, each said moiety being straight-chain or branched, and each of which groups is optionally mono- or polysubstituted in the aryl moiety by identical or different substituents, or a heterocyclyl radical, where the heterocyclyl radical is a furyl, furylmethyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrrolidinyl, piperidinyl, morpholinyl, or chromanyl group that is optionally mono- or polysubstituted by identical or different substituents,
• wherein the aryl or heterocyclyl substituents are selected from the group consisting of halogen;
• cyano;
• nitro;
• amino;
• methylenedioxy;
• N—(C1-C4-alkyl-carbonyl)amino;
• an alkyl, alkoxy, alkylthio, alkylsulphinyl, or alkylsulphonyl group, each of which groups is straight-chain or branched and has 1 to 6 carbon atoms;
• a halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonyl group, each of which groups is straight-chain or branched and has 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms;
• an alkoxycarbonyl or alkoximinoalkyl group, each of which groups is straight-chain or branched and has 1 to 6 carbon atoms in the individual alkyl moieties;
• and phenyl that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, a straight-chain or branched alkyl or alkoxy group, each of which groups has 1 to 6 carbon atoms, and a straight-chain or branched halogenoalkyl or halogenoalkoxy group, each of which groups has 1 to 6 carbon atoms and 1 to 3 identical or different halogen atoms, and
• R8 represents (i) hydrogen or represents straight-chain or branched alkyl that has 1 to 8 carbon atoms and is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of cyano;
• carboxyl;
• carbamoyl;
• thiocarbamoyl;
• halogen;
• an alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl, or alkylsulphonylaminocarbonyl group, each of which groups is straight-chain or branched and has 1 to 8 carbon atoms in the individual alkyl moieties;
• or heterocyclyl, where the heterocyclyl radical is a furyl, furylmethyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrrolidinyl, piperidinyl, morpholinyl, or chromanyl group;
• (ii) an alkenyl or alkynyl group, each of which groups has 2 to 8 carbon atoms and each of which groups is optionally mono- or polysubstituted by identical or different halogens;
• or (iii) cycloalkyl having 3 to 7 carbon atoms that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of cyano, halogen, and straight-chain or branched alkyl having 1 to 4 carbon atoms, or
• R8 together with R7 represents alkanediyl that has 2 to 6 carbon atoms and is optionally interrupted by O, S, NH, or N—(C1-C4-alkyl).