Salts of avermectins substituted in the 4″-position and having pesticidal properties

1. A compound of formula

wherein X − is an anion;

n is 1, 2, 3 or 4;

R 1 is C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl; or C 2 -C 12 alkenyl;

R 2 is mono- to penta-substituted C 1 -C 12 alkyl, unsubstituted or mono- to penta-substituted C 2 -C 12 alkenyl;

R 3 is mono- to penta-substituted C 1 -C 12 alkyl, unsubstituted or mono- to penta-substituted C 3 -C 12 cycloalkyl, unsubstituted or mono- to penta-substituted C 2 -C 12 alkenyl; unsubstituted or mono- to penta-substituted C 2 -C 12 alkynyl; or R 2 and R 3 together are a three- to seven-membered alkylene bridge, or a four- to seven-membered alkenylene bridge wherein a —CH 2 — group may have been replaced by O, S or NR 4 ;

wherein the substituents of the mono- to penta-substituted C 1 -C 12 alkyl, unsubstituted or mono- to penta-substituted C 3 -C 12 cycloalkyl, unsubstituted or mono- to penta-substituted C 2 -C 12 alkenyl, unsubstituted or mono- to penta-substituted C 2 -C 12 alkynyl are selected from the group consisting of OH, halogen, halo-C 1 -C 2 alkyl, CN, NO 2 , C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, norbomylenyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyl unsubstituted or substituted by from one to three methyl groups, C 3 -C 8 halocycloalkyl, C 1 -C 12 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 3 -C 8 cycloalkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 12 haloalkylthio, C 1 -C 12 alkylsulfinyl, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 12 haloalkylsulfinyl, C 3 -C 8 halocycloalkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 12 haloalkylsulfonyl, C 3 -C 8 halocycloalkylsulfonyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , —C(═O)R 5 , —NHC(═O)R 6 , —P(═O)(OC 1 -C 6 alkyl) 2 , aryl, heterocyclyl, aryloxy, heterocyclyloxy; and also aryl, heterocyclyl, aryloxy and heterocyclyloxy that, depending upon the possibilities of substitution at the ring, are mono- to penta-substituted by substituents selected from the group consisting of OH, halogen, CN, NO 2 , C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, dimethylamino-C 1 -C 6 alkoxy, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenoxy, phenyl-C 1 -C 6 alkyl; phenoxy unsubstituted or substituted by from one to three substituents selected independently of one another from halogen, methoxy, trifluoromethyl and trifluoromethoxy; phenyl-C 1 -C 6 alkoxy unsubstituted or substituted in the aromatic ring by from one to three substituents selected independently of one another from halogen, methoxy, trifluoromethyl and trifluoromethoxy; phenyl-C 2 -C 6 alkenyl, phenyl-C 2 -C 6 alkynyl, methylenedioxy, —C(═O)R 5 , —O—C(═O)R 6 , —NH—C(═O)R 6 , NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , C 1 -C 6 alkylsulfinyl, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 3 -C 8 halocycloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 haloalkylsulfonyl and C 3 -C 8 halocycloalkylsulfonyl;

R 4 is C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, benzyl or —C(═O)—R 5 ;

R 5 is H, OH, SH, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 12 alkylthio, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy; phenyl, phenoxy, benzyloxy, —NH-phenyl, —N(C 1 -C 6 alkyl)-phenyl, NH—C 1 -C 6 alkyl-C(═O)—R 7 , —N(C 1 -C 6 alkyl)-C 1 -C 6 alkyl-C(═O)—R 7 ; or phenyl, phenoxy, benzyloxy, NH-phenyl or —N(C 1 -C 6 alkyl)-phenyl substituted in the aromatic ring by from one to three substituents selected independently of one another from halogen, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy;

R 6 is H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, benzyl, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , —NH-phenyl or —N(C 1 -C 12 alkyl)-phenyl; and

R 7 is H, OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 2 -C 8 alkenyloxy, phenyl, phenoxy, benzyloxy, NH 2 , NH(C 1 -C 12 alkyl), N(C 1 -C 12 alkyl) 2 , —NH-phenyl or —N(C 1 -C 12 alkyl)-phenyl; and, where applicable, an E/Z isomer, E/Z isomeric mixture and/or tautomer thereof.

2. A compound according to claim 1 of formula (I) wherein R 1 is isopropyl or sec-butyl.

3. A pesticidal composition comprising as active ingredient at least one compound according to claim 1 of formula (I), in agrochemically acceptable salt form, and at least one adjuvant.

4. A method of controlling pests, which comprises applying a composition according to claim 3 to the pests or to the locus thereof.

5. A process for the preparation of a composition according to claim 3 comprising at least one adjuvant, which comprises intimately mixing and/or grinding the active ingredient with the adjuvant(s).

6. A method according to claim 4 for the protection of plant propagation material, which comprises treating the propagation material or the planting site of the propagation material.

7. Plant propagation material treated in accordance with the method described in claim 6 .