4″-deoxy-4″-(S)-amido avermectin derivatives

1. A compound of formula

that has the S-configuration at the 4″-position and wherein

the bond between carbon atoms 22 and 23 is a single or a double bond;

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

R 2 is H, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, —C(═O)—R 5 , aryl; wherein the C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, aryl substituents may be unsubstituted or mono-to penta-substituted;

R 3 is H, C 2 -C 12 alkenyl or C 2 -C 12 alkynyl; wherein the C 2 -C 12 alkynyl and C 2 -C 12 alkynyl substituents may be unsubstituted or mono-to penta-substituted;

X is a bond, O, NR 4 or S;

Z is C═O, C═S or SO 2 ;

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

R 2 and R 4 together are a three-to seven membered alkylene or alkenylene bridge, wherein the alkylene or elkenylene bridges are unsubstituted or mono to tri-substituted; and wherein one of the methylene groups of the three-to seven membered alkylene-or alkenylene-bridge may be replaced by O, NH, S, S(═O) or SO 2 ; and

wherein the substituents of the mentioned alkyl, alkeny, alkynyl, cycloalkyl, alkylene, alkenylene, aryl radicals as defined under R 2 , R 3 and R 4 are selected from the group consisting of OH, ═O, halogen, halo-C 1 -C 2 alkyl, CN, NO 2 , —N 3 , C 3 -C 8 cycloalkyl that is unsubstituted or substituted by from one to three methyl groups; norbornylenyl; C 3 -C 8 cycloalkenyl that is 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 alkythio, 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 , ═NO—C 1 -C 6 alkyl, —P(═O)(OC 1 -C 6 alkyl) 2 ; aryl, pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furyl, tetrahydrofuranyl, pyranyl, tetrahydropyranyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, quinolinyl, quinoxalinyl, benzofuranyl, benzimidazolyl, benzopyrrolyl, benzothiazolyl, indolyl, coumarinyl, indazolyl, aryloxy; and aryl, pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furyl, tetrahydrofuranyl, pyranyl, tetrahydropyranyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, quinolinyl, quinoxalinyl, benzofuranyl, benzimidazolyl, benzopyrrolyl, benzothiazolyl, indolyl, coumarinyl, indazolyl, and aryloxy that, depending upon the possibilities of substitution at the ring, are mono- to penta-substituted by substituents selected from the group consisting of OH, ═O, halogen, CN, NO 2 , —N 3 , 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 and phenyl-C 1 -C 6 alkyl; phenoxy that is 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 that is 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 8 , —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 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 3 -C 8 cycloalkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 6 alkoxy-C 1 -C 12 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 each of which is 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 6 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,-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;

or, where applicable, an E/Z isomer, a mixture of E/Z isomers and/or a tautomer, in each case in free form or in salt form;

with the proviso that Z is not C═O when X is a bond, R 2 is H, R 3 is hydrogen, the bond between carbon atoms 22 and 23 is a double bond and R 1 is i-propyl or sec-butyl.

2. A pesticidal composition comprising as active ingredient at least one compound of formula (I) as described in claim 1 , and at least one adjuvant.

3. A method of controlling pests, which comprises applying a composition as described in claim 2 to the pests or to the locus thereof.

4. A process for the preparation of a composition comprising at least one adjuvant, as described in claim 2 , which comprises intimately mixing and/or grinding the active ingredient with the adjuvant(s).

5. A method according to claim 3 for protecting a plant propagation material, which comprises treating the propagation material or a planting site of the propagation material.