# US 7,608,595 B2 · 4″-deoxy-4″-(S)-amido avermectin derivatives

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,608,595 B2
- Document ID: US7608595B2
- Status: Granted
- Kind: B2
- Application number: 10/513,247
- Filed: 2003-05-06
- Published: 2005-08-11
- Granted: 2009-10-27
- Earliest claimed: 2002-05-07
- Assignees: Merial Limited
- Inventors: Hans Tobler; Fiona Murphy Kessabi
- Web page: https://patentgrep.com/patent/US7608595B2

## CPC

- C07H 19/01: sharing oxygen
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

A compound of formula (I); 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; R1 is C1-C12alkyl, C3-C8cycloalkyl; or C2-C12alkenyl; R2 is H, or, for example, unsubstituted or mono- to penta-substituted C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl or C1-C6alkoxy-C1-C6alkyl; R3 is H or, for example, C1-C12alkyl; X is a bond, O, NR4 or S; and Z is C═O, C═S or S02; and, where applicable, E/Z isomers, mixtures of E/Z isomers and/or tautomers, in each case in free form or in salt form; a process for the preparation of and the use of those compounds and their isomers and tautomers; starting materials for the preparation of the compounds of formula (I); pesticidal compositions in which the active ingredient has been selected from those compounds and their tautomers; and a method of controlling pests using those compositions are described.

## Claims

### Claim 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;
R1 is C1-C12alkyl, C3-C8cycloalkyl; or C2-C12alkenyl;
R2 is H, C2-C12alkenyl, C2-C12alkynyl, —C(═O)—R5, aryl; wherein the C2-C12alkenyl, C2-C12alkynyl, aryl substituents may be unsubstituted or mono-to penta-substituted;
R3 is H, C2-C12alkenyl or C2-C12alkynyl; wherein the C2-C12alkynyl and C2-C12alkynyl substituents may be unsubstituted or mono-to penta-substituted;
X is a bond, O, NR4 or S;
Z is C═O, C═S or SO2;
R4 is H, C1-C8alkyl, C3-C8Cycloaklkyl, C2-C8alkenyl, C2-C8alkynyl benzyl or —C(═O)-R5; or
R2 and R4 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 SO2; and
wherein the substituents of the mentioned alkyl, alkeny, alkynyl, cycloalkyl, alkylene, alkenylene, aryl radicals as defined under R2, R3 and R4 are selected from the group consisting of OH, ═O, halogen, halo-C1-C2alkyl, CN, NO2, —N3, C3-C8cycloalkyl that is unsubstituted or substituted by from one to three methyl groups; norbornylenyl; C3-C8cycloalkenyl that is unsubstituted or substituted by from one to three methyl groups; C3-C8halocycloalkyl, C1-C12alkoxy, C1-C6alkoxy-C1-C6alkyl, C3-C8cycloalkoxy, C1-C12haloalkoxy, C1-C12alkythio, C3-C8cycloalkylthio, C1-C12haloalkylthio, C1-C12alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C12haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C12alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C12haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl, C2-C8alkynyl, NH(C1-C6alkyl), —N(C1-C6alkyl)2, —C(═O)R5, —NHC(═O)R6, ═NO—C1-C6alkyl, —P(═O)(OC1-C6alkyl)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, NO2, —N3, 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 and phenyl-C1-C6alkyl; phenoxy that is unsubstituted or substituted by from one to three substituents selected independently of one another from halogen, methoxy, trifluoromethyl and trifluoromethoxy; phenyl-C1-C6alkoxy 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-C2-C6alkenyl, phenyl-C2-C6alkynyl, methylenedioxy, —C(═O)R5,—O—C(═O)R8, —NH—C(═O)R6, NH2, NH(C1-C12alkyl), N(C1C12alkyl)2, C1-C6alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C6haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C6alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl and C3-C8halocycloalkylsulfonyl;
R5 is H, OH, SH, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, C1-C12alkyl, C3-C8cycloalkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C6alkoxy-C1-C12alkoxy, C1-C12alkylthio, C2-C8alkenyloxy, C2-C8alkynyloxy; phenyl, phenoxy, benzyloxy, NH-phenyl, —N(C1-C6alkyl)-phenyl, NH—C1-C6alkyl-C(═O)—R7, —N(C1-C6alkyl)-C1-C6alkyl-C(═O)—R7; or phenyl, phenoxy, benzyloxy, NH-phenyl or —N(C1-C6alkyl)-phenyl each of which is substituted in the aromatic ring by from one to three substituents selected independently of one another from halogen, C1-C6alkoxy, C1-C6haloalkyl and C1-C6haloalkoxy;
R6 is H, C1-C12alkyl, C1-C12haloalkyl, C2-C8alkenyl, C2-C6alkynyl, phenyl, benzyl, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, —NH-phenyl or —N(C1-C12alkyl)-phenyl; and
R7 is H, OH, C1-C12alkyl, C,-C12alkoxy, C1-C6alkoxy-C1-C6alkoxy, C2-C8alkenyloxy, phenyl, phenoxy, benzyloxy, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, —NH-phenyl or —N(C1-C12alkyl)-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, R2 is H, R3 is hydrogen, the bond between carbon atoms 22 and 23 is a double bond and R1 is i-propyl or sec-butyl.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 2)

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).

### Claim 5 (depends on 3)

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.