5-Halogenopyrazolecarboxamides

A 1-Methyl-3-dihalogenomethyl-5-halogenopyrazolecarboxamide of formula (I)

• in which
• T represents an oxygen or sulfur atom;
• R represents hydrogen, C1-C6-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkylsulfonyl, halo-C1-C4-alkoxy-C1-C4-alkyl or formyl;
• Hal1 and Hal2 independently of one another represent chlorine or fluorine;
• L represents phenyl which may be substituted by up to 4 identical or different groups R1;
• Q represents phenyl which may be substituted by up to 5 identical or different groups Rb;
• or
• Q represents halogen;
• nitro;
• cyano;
• isonitrile;
• hydroxyl;
• amino;
• sulfanyl;
• pentafluoro-λ6-sulfanyl;
• formyl;
• formyloxy;
• formylamino;
• optionally substituted (hydroxyimino)-C1-C8-alkyl;
• optionally substituted (C1-C8-alkoxyimino)-C1-C8-alkyl;
• optionally substituted (C2-C8-alkenyloxyimino)-C1-C8-alkyl;
• optionally substituted (C2-C8-alkynyloxyimino)-C1-C8-alkyl;
• optionally substituted (benzyloxyimino)-C1-C8-alkyl;
• carboxyl;
• carbamoyl;
• N-hydroxycarbamoyl;
• carbamate;
• optionally substituted C1-C16-alkyl;
• optionally substituted C2-C8-alkenyl;
• optionally substituted C2-C8-alkynyl;
• optionally substituted C1-C16-alkoxy;
• optionally substituted C1-C8-alkylsulfanyl;
• optionally substituted C1-C8-alkylsulfinyl;
• optionally substituted C1-C8-alkylsulfonyl;
• optionally substituted C1-C8-alkylamino;
• optionally substituted di-C1-C8-alkylamino;
• optionally substituted C2-C8-alkenyloxy;
• optionally substituted C3-C8-alkynyloxy;
• optionally substituted C3-C8-cycloalkyl;
• optionally substituted (C3-C8-cycloalkyl)-C1-C8-alkyl;
• optionally substituted (C3-C8-cycloalkyl)-(C3-C8-cycloalkyl;
• optionally substituted (C3-C8-cycloalkyl)-C2-C8-alkenyl;
• optionally substituted (C3-C8-cycloalkyl)-C2-C8-alkynyl;
• optionally substituted tri(C1-C8)alkylsilyl;
• optionally substituted tri(C1-C8)alkylsilyl-C1-C8-alkyl;
• optionally substituted C1-C8-alkylcarbonyl;
• optionally substituted C1-C8-alkylcarbonyloxy;
• optionally substituted C1-C8-alkylcarbonylamino;
• optionally substituted C1-C8-alkoxycarbonyl;
• optionally substituted C1-C8-alkyloxycarbonyloxy;
• optionally substituted C1-C8-alkylcarbamoyl;
• optionally substituted di-C1-C8-alkylcarbamoyl;
• optionally substituted C1-C8-alkylaminocarbonyloxy;
• optionally substituted di-C1-C8-alkylaminocarbonyloxy;
• optionally substituted N—(C1-C8-alkyl)hydroxycarbamoyl;
• optionally substituted C1-C8-alkoxycarbamoyl;
• optionally substituted N—(C1-C8-alkyl)-C1-C8-alkoxycarbamoyl;
• C1-C8-arylalkyl which is optionally substituted by up to 6 identical or different groups Rb;
• C2-C8-arylalkenyl which is optionally substituted by up to 6 identical or different groups Rb;
• C2-C8-arylalkynyl which is optionally substituted by up to 6 identical or different groups Rb;
• aryloxy which is optionally substituted by up to 6 identical or different groups Rb;
• arylsulfanyl which is optionally substituted by up to 6 identical or different groups Rb;
• arylamino which is optionally substituted by up to 6 identical or different groups Rb;
• C1-C8-arylalkyloxy which is optionally substituted by up to 6 identical or different groups Rb;
• C1-C8-arylalkylsulfanyl which is optionally substituted by up to 6 identical or different groups Rb;
• C1-C8-arylalkylamino which is optionally substituted by up to 6 identical or different groups Rb or a bicyclo[2.2.1]heptanyl group;
• R1, Rb independently of one another represent halogen;
• nitro, cyano, C1-C12-alkyl;
• C1-C6-haloalkyl having 1 to 9 identical or different halogen atoms;
• C1-C6-alkoxy;
• C1-C6-haloalkoxy having 1 to 9 identical or different halogen atoms;
• C1-C6-alkylsulfanyl;
• C1-C6-haloalkylsulfanyl having 1 to 9 identical or different halogen atoms;
• C1-C6-alkylsulfonyl;
• C1-C6-haloalkylsulfonyl having 1 to 9 identical or different halogen atoms;
• C2-C12-alkenyl;
• C2-C12-alkynyl;
• C3-C7-cycloalkyl;
• phenyl;
• tri(C1-C8)alkylsilyl;
• tri(C1-C8)alkylsilyl-C1-C8-alkyl;
• where, unless indicated otherwise, a group or a substituent which is substituted is substituted by at least one Rb;
• or
• Q and R1 together with the carbon atoms to which said Q and R1 are attached form an optionally susbstituted 5-, 6- or 7-membered carbocyclic or saturated heterocyclic ring;
• or
• Q and L together form a radical of the formula (W1),
• where
• the bond marked by * is attached to an amide;
• X represents a single bond or a double bond;
• Y represents oxygen, sulfur, N(R27) or (CR28R29)(CR30R31)m(CR32R33)n;
• m represents 0 or 1;
• n represents 0 or 1;
• R21 and R22 independently of one another represent hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R23, R24, R25 and R26 independently of one another represent hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, hydroxymethyl, C1-4-alkoxymethyl, C(O)CH3 or C(O)OCH3;
• R27 represents hydrogen, C1-C4-alkyl, benzyl where the phenyl group is optionally substituted up to three times by a radical independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy, formyl, C(O)C1-C4-alkyl optionally substituted by halogen or C1-C4-alkoxy, C(═O)O—C1-C6-alkyl optionally substituted by halogen, C1-C4-alkoxy or cyano or C1-C4-alkoxy-(C1-C4)-alkylene;
• R28, R29, R30, R31, R32 and R33 independently of one another represent hydrogen, halogen, hydroxyl, C1-C4-alkoxy, C1-C6-alkyl [optionally substituted by halogen, hydroxyl, C1-C4-alkoxy, ═O, aryl, O—C(O)—C1-C4-alkyl or a 3-7-membered carbocyclic ring which is itself optionally substituted by up to three methyl groups or C2-C6-alkenyl [optionally substituted by halogen, hydroxyl, C1-C4-alkoxy, ═O, aryl, O—C(O)—C1-C4-alkyl or a 3-7-membered carbocyclic ring which is itself optionally substituted by up to three methyl groups or a 3-7-membered saturated ring which is optionally substituted by up to three methyl groups and optionally contains a heteroatom selected from the group consisting of nitrogen and oxygen;
• or
• R28 and R29 together with the carbon atom to which said R28 and R29 are attached form a group C═O or a three- to five-membered carbocyclic ring which is optionally substituted by up to three methyl groups and optionally contains up to two heteroatoms independently selected from the group consisting of nitrogen and oxygen;
• or
• R28 and R29 together form a C1-C6-alkylidene which is optionally substituted by up to four groups that can be the same or different and that can be selected from the group in the list consisting of fluorine, chlorine, bromine and methyl, or a C3-C6-cycloalkylidene group which is optionally substituted by up to three methyl groups.