US 2013/0172390 A1 · Haloalkyl-Substituted Amides as Insecticides and Acaricides

Abstract

The present invention relates to halogen-substituted amide derivatives of the general formula (I) in which R1 to R6, Q1 to Q8, A, V, W, X, Y, n and m are each defined as described in the description—and to a process for preparation thereof and to the use thereof as insecticides and acaricides.

A compound of formula (I) and the diastereomers, enantiomers, E/Z isomers and salts thereof

where
R1 is hydrogen, halogen, nitro, cyano, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6-alkylsulphonylamino, tri(C1-C6-alkyl)silyl, aryl, hetaryl, aryl-C1-C4-alkyl, or hetaryl-C1-C4-alkyl,
where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulphenyl, C1-C6-alkylsulphonyl, aryl, hetaryl, arylalkyl or hetarylalkyl,
where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy or C1-C6-alkylthio,
or
R1 is a C1-C4 carbon chain which optionally contains 1-2 heteroatoms selected from the group consisting of N, S, and O, which is bonded to two adjacent ring positions and which forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring which is optionally mono or polysubstituted by C1-C6-alkyl or halogen, in which case n is 2,
n is 1, 2 or 3,
R2 is hydrogen, cyano, hydroxyl, amino, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, optionally monosubstituted or identically or differently polysubstituted aryl, hetaryl or optionally monosubstituted or identically or differently polysubstituted aryl-C1-C6-alkyl or hetaryl-C1-C4-alkyl,
where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, amino, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C4-alkylcarbonylamino or C1-C4-dialkylcarbonylamino,
or
R2 is an optionally mono- or polysubstituted C2-C4-alkyl chain which is optionally interrupted by O, S or N, forming, with Q1, a 5-7-membered ring optionally interrupted by O, S or N, and the substituents are each independently selected from halogen or C1-C6-alkyl,
R3 is hydrogen, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, aryl-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulphonyl, arylcarbonyl, hetarylcarbonyl, C1-C6-alkoxycarbonyl or aryloxycarbonyl,
where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, aryl, hetaryl, arylalkyl, hetarylalkyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl or C1-C4-dialkylaminocarbonyl, where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy or C1-C6-alkylthio,
V is a bivalent chemical moiety which is selected from —O— or —N(R8)—, and which is bonded to Q4 via a single bond, where the second (right-hand) connection site in each case is connected to Q4, where
R8 is hydrogen, cyano, hydroxyl, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, C1-C6-alkoxycarbonyl, arylalkyl or C1-C4-alkylsulphonyl,
where the substituents are each independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, C1-C4-alkoxycarbonyl, amino, C1-C6-alkylamino, C1-C6-dialkylamino, aminocarbonyl,
C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl and aryl-C1-C6-alkoxy,
R5 is hydrogen, halogen or optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl or C1-C6-alkoxy,
where the substituents are each independently selected from halogen or C1-C6-alkyl,
R6 is hydrogen, halogen, nitro, cyano, amino, hydroxyl, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl, C1-C6-alkylamino, formyl, (C1-C6-alkyl)carbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-dialkylamino, (C1-C6-alkylamino)carbonyl, (C1-C6-dialkylamino)carbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkylaminosulphonyl, C1-C6-alkylsulphonylamino, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, aryl, hetaryl, arylalkyl or hetarylalkyl,
where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy or C1-C6-alkylthio,
or
R6 is a C1-C4 carbon chain which optionally contains 1-2 heteroatoms selected from the group consisting of N, S, and O, which is bonded to two adjacent ring positions Q4 to Q8 and forms an aliphatic, aromatic or heteroaromatic ring which is optionally mono- or polysubstituted by C1-C6-alkyl or halogen, in which case m is 2,
m is 0, 1, 2, or 3,
X is unsubstituted C1-C6-haloalkyl,
W is O,
A-Y together are cyano, or are optionally mono- or polysubstituted hetaryl, heterocyclyl or oxoheterocyclyl,
where the substituents are selected from halogen, nitro, cyano, amino, hydroxyl, from optionally monosubstituted or identically or differently polysubstituted amino,
C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, aryl, hetaryl, C1-C6-arylalkyl, C1-C6-hetarylalkyl, aryloxy, hetaryloxy, sulphonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkoxycarbonyl or C1-C6-alkylaminocarbonyl,
where the substituents are each independently selected from halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, (C1-C6-alkoxy)carbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, C3-C6-cycloalkylamino, (C1-C6-alkyl)C3-C6-cycloalkylamino or di(C1-C4)alkylamino,
or
A is a bivalent chemical moiety which is selected from the moieties —NR13C(═O)—, —C(R11)(R12)NR13C(═O)—, —C(R11)(U)NR13C(═O)—, —C(R11)(R12)N(U)C(═O)—, —C(═O)NR13—, —C(═O)NR13CH2, —C(═O)O, —C(═O)NR13CH2C(═O)NR14—, —C(═O)NR13NR14—, —C(R11)(R12)NR13—, —S(═O)2NR13—, —C(R11)(R12)NR13S(═O)2—, or —C(═O)N(R3)—O—, where the first (left-hand) connection site in the bivalent chemical moieties in each case is connected to the ring at one of positions Q4 to Q8 and the second (right-hand) connection site in each case to Y,
where U is an optionally substituted C2-C4-alkyl which, together with a carbon atom adjacent to the connection site of A to the ring at positions Q4 to Q8, forms a 5-7-membered ring,
where the substituents are each independently selected from C1-C3-alkyl, C1-C3-alkoxy or halogen,
R11 and R12 are each independently hydrogen, cyano or optionally monosubstituted or identically or differently polysubstituted C1-C4-alkyl, or C3-C6-cycloalkyl,
where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy,
or
R11 and R12 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-6-membered ring which optionally contains one to two double bonds,
or
R11 and R13 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-7-membered ring which optionally contains one to two double bonds,
and where R13 and R14 are each independently hydrogen, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy,
or
R13 and R14 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-7-membered ring which optionally contains one to two double bonds,
Y is hydrogen, optionally monosubstituted or identically or differently polysubstituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, aryl, hetaryl, heterocyclyl or oxoheterocyclyl,
where the substituents are selected from halogen, nitro, cyano, or hydroxyl, from optionally monosubstituted or identically or differently polysubstituted amino, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6-alkylsulphonylamino, aryl, hetaryl, C1-C6-arylalkyl, C1-C6-hetarylalkyl, aryloxy, hetaryloxy or heterocyclyl, C1-C6-alkoxy, C1-C6-alkyl, C1-C6-alkylcarbonyl, sulphonyl, sulphinyl, C1-C6-alkylthio, or C1-C6-alkoxycarbonyl,
where the substituents are each independently selected from halogen, C1-C6-alkyl, hydroxyl, amino, C1-C6-alkylcarbonyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkylcarbonyl, cyano, nitro, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, (C1-C6-alkoxy)carbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, C3-C6-cycloalkylamino, (C1-C6-alkyl)C3-C6-cycloalkylamino, di(C1-C4)alkylamino or C1-C6-alkylaminocarbonyl,
Q1 to Q3 are each independently a carbon atom which is substituted by hydrogen or by R1,
Q4 is a carbon atom,
and
Q5 to Q8 are each independently a carbon atom which is substituted by hydrogen, by R6, or A-Y,
where exactly one of Q5, Q6, Q7, Qs is substituted by A-Y.

48 more elements

Haloalkyl-Substituted Amides as Insecticides and Acaricides

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Haloalkyl-Substituted Amides as Insecticides and Acaricides

Life of this patent

Abstract

Claims13