Patent IL-42156-A (IL)
Title: Substituted butenoic acid derivatives their manufacture and use as pesticides
IPC: C07C59/60
Filed: 1973-05-01
Abstract: 1422181 Aromatic derivatives of but-2- enoic acid CIBA-GEIGY AG 9 May 1973 [10 May 1972 29 Sept 1972 29 March 1973] 22213/73 Heading C2C The invention comprises a compound of Formula I wherein R 1 represents a cyclohexyl or cyclohexyloxy group or a group of Formula Ia in which n represents 0 or 1, Y represents an oxygen atom or a group of formula and R 6 represents a hydrogen or halogen atom or a C 1-5 alkyl or alkoxy group and R 7 represents a C 1-3 alkyl, formyl or acetyl group; R 2 represents a hydrogen or halogen atom, CH 3 or C 2 H 5 ; R 3 represents H, CH 3 or C 2 H 5 ; R 4 represents a hydrogen atom or a C 1-3 alkyl group; R<SP>5</SP> represents a carboxyl, (C 1-5 alkoxy)carbonyl, unsubstituted or halosubstituted (C 3-5 alkenyloxy)carbonyl, (C 3-5 alkynyloxy)carbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl or cyano group or a group of Formula Ib in which R 8 represents a hydrogen atom or a C 1-5 alkyl, C 3-5 alkenyl, or C 3-5 alkynyl group and R 9 represents a C 1-5 alkyl, C 3-5 alkenyl or C 3-5 alkynyl group or R 8 and R 9 together with their attached nitrogen represent a saturated heterocyclic group having 5 or 6 ring atoms which atoms may comprise an oxygen, sulphur or further nitrogen atom; Z represents -O-, -NH-, -NR 7 - or -CH(R 10 )O- the latter being carbon linked to the phenyl nucleus and R 10 being H or C 1-3 alkyl. The compounds of Formula I may be prepared by reacting (a) a compound of Formula II in the presence of a base with a compound of Formula III (III) X-CHR 3 -CR 4 = CH-R 5 in which R 1 to R 5 and z are as defined above and x-halogen, (b) a compound of Formula V with a compound of Formula VIII R 1 to R 5 and z being as defined above, R 11 represents a C 1-5 alkyl, phenyl or p-chlorophenyl group and Me represents an alkali or alkaline earth metal of valency n, (c) a compound of Formula IX (i) in the presence of an acid catalyst with a compound of formula R 12 OH or (ii) in the presence of a base with a compound of formula R 12 X wherein R 12 represents a C 1-5 alkyl, C 3 to C 5 alkenyl, C 3 to C 5 alkynyl or cyclohexyl group and X is halogen to obtain compounds of Formula I in which R 1 to R 4 and z are as defined above and R 5 represents a (C 1-5 alkoxy)carbonyl, (C 3-5 alkenyloxy)carbonyl, (C 3-5 alkynyloxy)- carbonyl or cyclohexyloxycarbonyl groups or (d) a compound of Formula I in which Y and/or Z represents -NH- with an alkylating or acylating agent to obtain compounds of Formula I in which Y and/or Z represents -NR 7 - R 7 being as defined above other than hydrogen. 1 - [4 - Benzylphenoxy]propan - 2 - one, 1 - [4 - phenoxyphenoxy] - propan - 2 - one, 1 - [4 - benzoylphenoxy]propan - 2 - one and 2 - [4 - phenoxyphenoxy] - butan - 3 - one are prepared by hydrolysis of their dimethyl ketals. 1 - [4 - Benzylphenoxy] - propan - 2 - ondimethylketal is prepared by reacting 4- benzylpropargyloxybenzene with a mixture of HgO, CCl 3 CO 2 H, BF 3 .(C 2 H 5 ) 2 O and CH 3 OH. Pesticidal compositions comprise a compound of Formula I together with a solid extender, a solid extender and a surface active agent or a liquid diluent and a surface active agent.
[GB1422181A]