Avermectin and avermectin monosaccharide derivatives substituted in the 4″-or 4′-position having pesticidal properties

A compound of the formula (I)

• U is —N(R2)OR3 or —N+(O−)═C(RE)(RZ);
• n is 0 or 1;
• X—Y is —CH═CH— or —CH2—CH2—;
• R1 is C1-C12alkyl, C3-C8cycloalkyl or C2-C12alkenyl;
• R2 and R3 are, independently from each other, —Q, —C(O)—Z—Q or —CN;
• RZ and RE are, independently from each other, —Q, —C(O)—Z—Q or —CN;
• or
• RZ and RE together are a three- to seven membered alkylene or alkenylene bridge, which is unsubstituted or mono- to tri-substituted;
• Z is a bond, O or —NR4—;
• R4 is H, C1-C8alkyl, hydroxy-C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, phenyl, benzyl —C(═O)R5, or —CH2—C(═O)—R5;
• Q is H, C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C3-C12-cycloalkyl, C5-C12-cycloalkenyl, aryl, or heterocyclyl, which are unsubstituted or mono- to pentasubstituted;
• wherein the alkyl-, alkenyl-, alkynyl-, alkylene-, alkenylene-, cycloalkyl-, cycloalkenyl-, aryl- and heterocyclyl-radicals of the substituents Q, R2, R3, R4, RZ, RE and Q are independently of each other selected from the group consisting of OH, ═O, SH, ═S, halogen, CN, —N3, SCN, NO2, Si(C1-C8alkyl)3, halo-C1-C2alkyl, C1-C2alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, C2-C12alkenylthio, C2-C12haloalkenylthio, C2-C12alkenylsulfinyl, C2-C12haloalkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12haloalkenylsulfonyl, C3-C8cycloalkyl which is unsubstituted or substituted by one to three methyl groups, norbornylenyl, C3-C8halocycloalkyl, C1-C12alkoxy, C3-C8cycloalkoxy, C1-C12alkylthio, C3-C8cycloalkylthio, C1-C12haloalkylthio, C1-C12alkyl-sulfinyl, 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, heterocyclylthio;
• wherein the aryl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy, arylthio, benzylthio and heterocyclylthio radicals are either unsubstituted or, depending on the possibilities of substitution on the ring, mono- to pentasubstituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C1-C12haloalkyl, Si(C1-C8alkyl)3, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, C3-C8cycloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio, C1-C12haloalkylthio, C1-C6alkoxy-C1-C6alkyl, dimethylamino-C1-C6alkoxy, C2-C8alkenyl, C2-C8alkynyl, phenoxy, phenyl-C1-C6alkyl, methylene-dioxy, —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;
• R5 is H, OH, SH, —N(R8)2 wherein the two R8 are independent of each other, C1-C24alkyl, C2-C12alkenyl, C1-C8hydroxyalkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkyl, C1-C12alkylthio, C2-C8alkenyloxy, C3-C8alkynyloxy, Si(C1-C8alkyl)3, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, 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 independently of one another, depending on the substitution possibilities, mono- to trisubstituted in the ring 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, Si(C1-C8alkyl)3, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, (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, Si(C1-C8alkyl)3, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy and C1-C12halo-alkylthio;
• R7 is H, OH, C1-C24alkyl that is optionally substituted with OH, or —S(O)2—C1-C6alkyl;
• C1-C12alkenyl, C2-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 is H, C1-C6alkyl, which is optionally substituted with one to five substituents selected from the group consisting of halogen, hydroxy, cyano C1-C6alkoxy, ═O, C2-C12alkenyl, C2-C12haloalkenyl, C2-C12haloalkynyl and C3-C12haloalkynyloxy;
• C3-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, Si(C1-C8alkyl)3, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, 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, OH, ═O, C2-C12alkenyl, C2-C12haloalkenyl, C2-C12haloalkynyl, C2-C12haloalkynyl 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, Si(C1-C8alkyl)3, C1-C12alkoxy, C1-C12alkoxy-C1-C12alkoxy, C1-C12haloalkoxy, C3-C8cycloalkoxy, C2-C12alkenyloxy, C2-C12haloalkenyloxy, C2-C12haloalkenyl, C3-C12alkynyloxy, C2-C12haloalkynyl, C3-C12haloalkynyloxy, C1-C12alkylthio and C1-C12haloalkylthio;
• or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer thereof.