3,5-DIALKYL-4-HYDROXYGENZOATES THIONOBENZOATES, THIOLOBENZOATES AND DITHIOBENZOATES AND THEIR INSECTICIDAL COMPOSITIONS

摘要

1421976 Ablialkyl hydroxybenzoates and their sulphur analogues CHEVRON RESEARCH CO 14 Aug 1973 [16 Aug 1972 5 July 1973] 39527/73 Heading C2C The novel compounds of general Formula I wherein Y is S or O; U is S or O; RSP1/SP and RSP2/SP are, independently, branched C 3-6 alkyl groups attached to the ring by a secondary or tertiary carbon atom and RSP3/SP is (a) C 4-6 tert-alkyl, (b) C 3-10 cycloalkyl, (c) C 3-6 alkenyl, (d) C 3-6 alkynyl, (e) C 2-6 alkoxymethyl, (f) C 2-6 alkylthiomethyl, (g) C 7-12 phenalkyl optionally substituted on the ring with 1 or 2 substituents selected from C 1-4 alkyl, C 1-4 alkoxy, F, Cl, Br and alkylenedioxy of 1-4 carbon atoms, (h) C 1-4 alkyl substituted with a mono or bicyclic heterocyclic group having 3 to 10 carbon atoms and 1 to 3 atoms selected from O, N or S or (i) a mono- or bicyclic heterocyclic group having from 3 to 10 carbon atoms and 1 to 3 hetero atoms selected from O, S and N provided that (i) when RSP1/SP is isopropyl, RSP2/SP is t-butyl, Y is O and U is O then RSP3/SP is not cyclohexyl and (ii) when RSP1/SP and RSP2/SP are t-butyl, Y is O and U is S, RSP3/SP is not benzyl or 4-t-butyl benzyl may be prepared by (a) reaction of compounds of Formula II with an organic halide of formula RSP3/SPX - wherein M is a metal cation and X is a halogen, (b) reacting a compound of Formula V with a mercaptan or alcohol of formula RSP3/SPUH in the presence of an acid acceptor (X being a halogen), or (c) reacting a compound of Formula VIII with an olefin of formula IX wherein RSP4/SP and RSP5/SP are H or C 1-4 alkyl or RSP6/SP and RSP7/SP are independently H, C 1-4 alkyl, phenyl optionally substituted by 1 or 2 substituents selected from alkyl, alkoxy, F, Cl, or alkylenedioxy or a heterocyclic radical of 3 to 10 carbon atoms and 1 to 3 heteroatoms selected from O, S and N provided that only one of RSP6/SP and RSP7/SP is alkyl, phenyl or substituted phenyl or heterocyclic. 3,5 - Di - t - butyl - 4 - hydroxythiolobenzoic acid is prepared by reacting 2,6-di-t-butylphenol with NaH followed by reaction with carbon oxysulphide. Insecticidal compositions having morphogenetic hormonal mimetic activity comprise a compound of Fcrmula I in which RSP1/SP, RSP2/SP, RSP3/SP U and Y are as defined above except that RSP3/SP may be any C 1-6 aklyl group or a C 7-12 phenalkyl group optionally substituted as defined above for C 7-10 phenalkyl groups or one of the compounds excluded by the provisos associated above with Formula I together with a biologically inert carrier.