Avermectin B1 and avermectin B1 monosaccharide derivatives having an alkoxymethyl substituent in the 4″-or 4′-position
What is described are a compound of the formula wherein n is 0 or 1; A-B is —CH═CH— or —CH 2 —CH 2 —; R 1 is C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or C 2 -C 12 -alkenyl; R 2 is for example C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl or C 2 -C 12 -alkinyl; which are optionally substituted with one to five substituents selected from the group consisting of OH, halogen, CN, —N 3 , —NO 2 , C 3 -C 8 -Cycloalkyl, norbornylenyl-, C 3 -C 8 -Cycloalkenyl; C 3 -C 8 -halocycloalkyl, C 1 -C 12 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, 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, —NR 4 R 6 , —X—C(═Y)—R 4 , —X—C(═Y)—Z—R 4 , —P(═O)(OC 1 -C 6 -alkyl) 2 , aryl, heterocyclyl, aryloxy, arylthio and heterocyclyloxy; R 3 is for example H, C 1 -C 12 -alkyl or C 1 -C 12 -alkyl which is optionally substituted and, where applicable, to E/Z isomers, mixtures of E/Z isomers and/or tautomers, in each case in free form or in salt form; a process for preparing and using these compounds and their tautomers; pesticides whose active compound is selected from these compounds and their tautomers; and a process for preparing these compounds and compositions, and the use of these compounds and compositions.
1. A compound of formula (I):
wherein
n is 0 or 1;
A-B is —CH═CH— or —CH 2 —CH 2 —;
R 1 is C 1 -C 12 -alkyl, C 3 -C 5 -cycloalkyl or C 2 -C 12 -alkenyl;
R 2 and R 3 together are a three- to seven-membered alkylen- or a four- to seven-membered alkenylen bridge, wherein one or two CH 2 -groups may independently of each other be replaced by a group —C(═O)—, —C(═S)—, O, S, —NR 5 , —OC(═O)—O, —OC(═O)S—, —OC(═O)N(R 5 )—, —C(═O)O—, —C(═O)S, —C(═O)N(R 5 )—, —N(R 5 )C(O)S—, —N(R 5 )C(═O)N(R 5 )—, and wherein the alkylene or alkenylen bridge may be independently of each other be substituted with one or two substituents selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkyl;
R 5 is H, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, benzyl or —C(═O)—C 1 -C 12 -alkyl; and, where applicable, to E/Z isomers, mixtures of E/Z isomers and/or tautomers, in each case in free form or in salt form;
with the proviso, that the compound is not the B1a or B1b derivative when n is 1, and R 2 and R 3 together are unsubstituted —CH 2 —CH 2 —CH 2 —CH 2 —.
2. A compound according to claim 1 wherein R 1 is isopropyl or sec-butyl.
3. A pesticide which contains at least one compound of the formula (I) as described in claim 1 as active compound and at least one auxiliary.
4. A method for controlling pests wherein a composition as described in claim 3 is applied to the pests or their habitat.