Avermectins substituted in the 4″-position having pesticidal properties

A compound of the formula

• in which
• R1 is C1-C12alkyl, C3-C8cycloalkyl or C2-C12alkenyl;
• R2 is H, unsubstituted or mono- to pentasubstituted C1-C12alkyl or unsubstituted or mono- to pentasubstituted C2-C12alkenyl;
• R3 is, mono- to pentasubstituted C1-C12alkyl, unsubstituted or mono- to pentasubstituted C3-C12cycloalkyl, unsubstituted or mono- to pentasubstituted C1-C6alkoxy-C1-C6alkyl, unsubstituted or mono- to pentasubstituted C2C12alkenyl, unsubstituted or mono- to pentasubstituted C2-C12alkynyl;
• or
• R2 and R3 together are a three- to seven-membered alkylene or a four- to seven membered alkenylene bridge, in which a CH2 group may be substituted by O, S or NR4;
• in which the substituents of the mono- to pentasubstituted C1-C12 alkyl, mono- to pentasubstituted C3-C12cycloalkyl, mono- to pentasubstituted C1-C6alkoxy-C1-C6alkyl, mono- to pentasubstituted C2-C12alkenyl, or mono- to pentasubstituted C2-C12alkynyl groups are selected from the group consisting of OH, halogen, halo-C1-C2alkyl, CN, SCN, NO2, C2-C6alkynyl, C3-C8-cycloalkyl which is unsubstituted or substituted by one to three methyl groups;
• norbornylenyl, C3-C8cycloalkenyl which is unsubstituted or substituted by one to three methyl groups;
• C3-C8halocycloalkyl, C1-C12alkoxy, C3-C8cycloalkoxy, C1-C12alkylthio, C3-C8cycloalkylthio, C1-C12-haloalkylthio, C1-C12alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C12haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C12alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C12haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl, C2-C8alkynyl, —N(R8)2, wherein the two R8 are independent of each other;
• —C(═O)R5, —O—C(═O)R6, —NHC(═O)R5, —S—C(═S)R6, —P(═O)(OC1-C6alkyl)2, —S(═O)2R9;
• —NH—S(═O)2R9, —OC(═O)—C1-C6alkyl-S(═O)2R9,
• aryl, benzyl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy, arylthio, benzylthio, and heterocyclylthio;
• wherein said aryl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy, arylthio, benzylthio or heterocyclylthio may be unsubstituted or, depending on the possibilities of substitution on the ring, are mono- to pentasubstituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C3-C8cycloalkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio, C1-C12haloalkylthio, C1-C6alkoxy-C1-C6alkyl, dimethylamino-C1-C6alkoxy, C2-C8alkenyl, C2-C8alkynyl, phenoxy, phenyl-C1-C6alkyl;
• methylenedioxy, —C(═O)R5, —O—C(═O)—R6, —NH—C(═O)R6, —N(R8)2, wherein the two R8 are independent of each other;
• C1-C6alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C6haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C6alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl and C3-C8halocycloalkylsulfonyl;
• R4 is H, C1-C8alkyl, hydroxy-C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, phenyl, benzyl, —C(═O)R5, or —CH2—C(═O)—R5;
• R5 is H, OH, SH, —N(R8)2, wherein the two R8 are independent of each other;
• C2-C12alkenyl, C1-C8hydroxyalkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12--haloalkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkyl, C1-C12alkylthio, C2-C8alkenyloxy, C2-C8alkynyloxy, NH—C1-C6alkyl-C(═O)R7, —N(C1-C6alkyl)-C1-C6alkyl-C(═O)—R7, —O—C1-C2alkyl-C(═O)R7, —C1-C6alkyl-S(═O)2R9;
• aryl, benzyl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy;
• or aryl, benzyl, heterocyclyl, aryloxy, benzyloxy or heterocyclyloxy, which are unsubstituted or mono- to trisubstituted in the ring independently of one another by halogen, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6haloalkyl or C1-C6haloalkoxy;
• R6 is H, C1-C24alkyl, C1-C12haloalkyl, C1-C12hydroxyalkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C6alkoxy-C1-C6alkyl, (NR8)2, wherein the two R8 are independent of each other;
• —C1-C6alkyl-C(═O)R8, —C1-C6alkyl-S(═O)2R9, aryl, benzyl, heterocyclyl;
• or aryl, benzyl or heterocyclyl which, depending on the possibilities of substitution on the ring, are mono- to trisubstituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio and C1-C12haloalkylthio;
• R7 is H, OH, C1-C24alkyl which is optionally subsituted with OH, or —S(═O)2—C1-C6alkyl;
• C1-C12alkenyl, C1-C12alkynyl, C1-C12alkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, C2-C8alkenyloxy, aryl, aryloxy, benzyloxy, heterocyclyl, heterocyclyloxy or —N(R8)2, wherein the two R8 are independent of each other;
• R8 H, C1-C6alkyl, which is optionally substituted with one to five substituents selected from the group consisting of halogen, C1-C6alkoxy, hydroxy and cyano;
• C1-C8-cycloalkyl, aryl, benzyl, heteroaryl;
• or aryl, benzyl or heteroaryl, which, depending on the possibilities of substitution on the ring, are mono- to trisubstituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio and C1-C12haloalkylthio;
• R9 is H, C1-C6alkyl, which is optionally substituted with one to five substituents selected from the group consisting of halogen, C1-C6alkoxy, hydroxy and cyano;
• aryl, benzyl, heteroaryl;
• or aryl, benzyl or heteroaryl, which, depending on the possibilities of substitution on the ring, are mono- to trisubstituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio and C1-C12haloalkylthio;
• with the proviso that R1 is not sec-butyl or isopropyl if R2 is H and R3 is 2-hydroxyethyl, or benzyl;
• or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer thereof.