US 12,528,800 B2 · Pesticidal compounds

Abstract

The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description, (I) The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

A compound of formula I

wherein
A is N or CRA;
B1 is N or CRB1;
B2 is N or CRB2;
B3 is N or CRB3;
B4 is N or CRB4;
W is O, S(═O)m, or NR6;
RA is H, halogen, N3, OH, CN, NO2, —SCN, —SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxyl-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or RA is C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthiol, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
RB1, RB2, RB3, and RB4 independently of each other are H, halogen, N3, OH, CN, NO2, —SCN, —SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or RB1, RB2, RB3, and RB4 independently of each other are C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe,
phenyl, phenoxy, phenylcarbonyl, phenylthiol, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Q is —C(R4R5)—O—, —C(═O)—O—, —S(═O)m—C(R7R8)—, —N(R2)—S(═O)m—, —N(R2)—C(R9R10)—, —C(═O)—C(R19R20)—, —N(R2)—C(═O)—, —N(R2)—C(═S)—, —C(R13R14)—C(R15R16)—, —N=C(X)—, or —N(R2)—C(═NR)—;
wherein Ar is bound to either side of Q;
m is 0, 1, or 2;
X is H, halogen, SR7, OR8, or N(R3)2;
R is H, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, or C3-C6-cycloalkyl, wherein the alkyl, alkenyl, and cycloalkyl moieties are unsubstituted or substituted with halogen, or R is selected from OR8 or N(R3)2;
R3 is H, C1-C6-alkyl, or C1-C6-alkoxy-C1-C4-alkyl;
R2 is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, or C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or R2 is C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R4, R5, R7, R8, R9, R10, R13, R14, R15, R16, R19, R20 independently of each other are H, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxyl-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or R4, R5, R7, R8, R9, R10, R13, R14, R15, R16, R19, R20 independently of each other are C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R6 is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxyl-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or R6 is C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C5-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, —CH2—C(═O)—ORa, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RAr, wherein
RAr is halogen, N3, OH, CN, NO2, —SCN, —SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxyl-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, RAr is C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
R1 is a moiety selected from the group consisting of YZT-1 to YZT-8, wherein
denotes attachment to the 6 membered ring:
R11 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or R11 is C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, aryl, aryl-carbonyl, aryl-C1-C4-alkyl, aryloxy-C1-C4-alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, wherein when the aryl groups are a phenyl, the phenyl groups are unsubstituted or substituted with R9 and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9-, or 10-membered bicyclic hetaryl;
R12 is a radical of the formula A1;
wherein # indicates the point of attachment to the remainder of R1;
R121, R122, R123 independently of each other are H, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkenylcarbonyloxy, or C3-C6-cycloalkylcarbonyloxy, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, or R121, R122, R123 independently of each other are NRbRc, or one of R121, R122, or R123 may be oxo;
R124 is H, C1-C6-alkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, or C2-C6-alkenyloxy, wherein the alkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or substituted with halogen;
and where
Rya is H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or wherein Rya is C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Ryc, Rzc are, identical or different, H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;
RT is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or wherein RT is C(═O)—ORa, C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where wherein when the C1-C6-alkylene is linear and in the linear C2-C6-alkenylene a CH2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Rza is H, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, or C1-C4-alkyl-C3-C6-cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or Rza is C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, C(═O)—NRbRc, C(═O)—Rd, phenyl, phenylcarbonyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, wherein when the C1-C6-alkylene is linear and in the linear C2-C6-alkenylene a CH2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Ra, Rb, Rc are, identical or different, H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or Ra, Rb, Rc are, identical or different, C1-C6-alkylene-CN, phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rd is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or Rd is phenyl, or —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Re is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, wherein the alkyl, and cycloalkyl moieties are unsubstituted or substituted with halogen,
or phenyl and —CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;
Rf is halogen, N3, OH, CN, NO2, —SCN, —SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxyl-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or Rf is C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(═O)mRe;
Rg is halogen, N3, OH, CN, NO2, —SCN, —SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxyl-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C6-cycloalkoxy-C1-C4-alkyl-, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, or Rg is C(═O)—ORa, NRbRc, C1-C6-alkylene-NRbRc, O—C1-C6-alkylene-NRbRc, C1-C6-alkylene-CN, NH—C1-C6-alkylene-NRbRc, C(═O)—NRbRc, C(═O)—Rd, SO2NRbRc, or S(=O)mRe;
Rh is halogen, OH, C1-C6-alkyl, C3-C6-cycloalkyl, or CN;
and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof,
wherein the compound tert-butyl-N-[4-(5-[3-(aminocarbonyl)-2,4-difluorophenoxy]methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamate is excluded.

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Pesticidal compounds

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Pesticidal compounds

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Abstract

Claims13