Pesticidal compounds

Claim 1

1) A compound of the formula (1): wherein R is C 2-10 alkyl, alkenyl or alkynyl, each optionally substituted by , or methyl substituted by; cyano, C 3-4 cycloalkyl,halo, C 1-4 alkoxy or a group S(O)m R 4 where R 4 is C 1-4 alkyl and m is 0, 1 or 2, or Ris C 3-10 cycloalkyl, C 4-10 cycloalkenyl or phenyl, each optionally substituted by C 1-4 alkox y, C 1-3 alkyl, C 2-4 alk y n y l , halo , cyano or a group S (O)m R 4 as defined hereinbefore; R is halo, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C 1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R 4 as defined hereinbefore or alkynyl substituted by tri-C 1-4 alkylsilyl, or R is cyano, spiro-cyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano or C 1-3 alkyl optionally substituted by fluorine, or R and R and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by halo, C 1-3 alkyl or alkoxy or C 2-3 alkenyl, R is phenyl, C 5 -10 cycloalkyl or cycloalkenyl each optionally substituted and R 3 is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo,or R is cyano or halo. 2) A compound according to claim 1 in which R is n-propyl,n-butyl, i-butyl, s-butyl, t-butyl, cyclopentyl or cyclohexyl. 3) A compound according to either claim 1 or 2 in which R is methyl, ethyl, trifluoromethyl, cyano or ethynyl. 4) A compound according to any oneof claims 1 to 3 inwhich R is cyclohexyl, cycloheptyl, cyclooctyl or phenyl optionally substituted at the 3-, 4- and/or 5- position by halo, cyano, C 2-3 alkynyl, azido or nitro and/or at the 2- and/or 6- position by fluoro. 5) A compound according to claim 4 in which R 2 is phenyl substituted at the 4-position by chlorine, bromine or ethynyl. 6) A compound according to any one of claims 1 to 5 in which R is hydrogen or methyl. 7) A compound of the formula IA: wherein R a is C 2-4 alkyl, alkenyl or alkynyl, C 5-10 cycloaklyl or phenyl, each optionally substituted by cyano or C 1-4 alkoxy, R is cyano or C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkoxy, C 1-4 alkylthio or halo,or R 1a is cyano, gem dimethyl or R 1a and R a and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by C 1-3 alkyl or alkoxy; R 2a is phenyl, C 5-10 cycloaklyl or cycloalkenyl each optionally substituted and R 3a is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo. 8) 1-(4-bromophenyl)-4-cyclohexyl-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-chlorophenyl)-3-methyl-4-iso-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-3-methyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-chlorophenyl)-3-methyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-cyclohexyl-3-methyl-4-iso-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-4-t-butyl-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 1,4-dicyclohexyl-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-I-(4-chlorophenyl)-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-ethynylphenyl)-3-meihyl-4-n-proayl-2,6,7-trioxabicyclo[2,2,2)octane, 3-methyl-4-n-propyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo-[2,2,2]octane, 1-(4-ethynylphenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicycloj2,2,2]octane, 4-n-propyl-3-tritJuoromethyl-1-[4-(2-trimethylsilylethynyl)-phenyl)-2,6,7- trioxabicyclo[2,2,2]octane, 1-(4-chlorophenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-4-n-propyl-3-trifJuoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-chlorophenyl)-4-cyclohexyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-4-cyclohexyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-3-ethenyl-4-n-propyl-2,6,7-trioxabieyclo[2,2,2]octane, 1-cyclohexyl-4-n-propyl-3-trifluoromethyl[2,6,7]trioxabicyclo[2,2,2)octane, 1-(4-bromophenyl)-3-cyano-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 3-cyano-1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-4-cyclohexyl-3-methoxymethyl-2,6,7-trioxabicyclo[2,2,2]octane. 1-cyclohexyl-3-methyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-bromophenyl)-4-t-butyl-3-ethyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-1-cyclohexyl-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-(4-chlorophenyl)-3,5-dimethyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, ]-(4-bromophenyl)-3,5-dimethyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 1-clohexyl-3,5-dimethyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane and 1-(4-cyanophenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2)octane, 1-(4-bromophenyl)-4-n-butyl-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-n-butyl-1-(4-chlorophenyl)-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane 4-t-butyl-3-cyano-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2,2,2)octane 1-(4-cyanophenyl)-3-ethynyl-4-isopropyl-2,6,7-trioxabicyclo[2,2,2)octane 3-cyano-1-(4-cyanophenyl)-4-isopropyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-3-cyano-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2,2,2]octane 4-t-butyl-3-cyano-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2.2.2] octane 1-(4-bromo-3,5-dichlorophenyl)-4-n-propyl-3-trifluoromethyl- 2,6,7-trioxabicyclot2,2,2]-octane or 1-(4-bromo-3-chlorophenyl)-4-n-propyl-3-trifluoromethyl- 2,6,7-trioxabicyclo [2,2,2]-octane, or 4-n-Butyl-1-(4-bromophenyl)-3-trifluoromethyl-2,6,7- trioxabicyclo[2.2.2]octane, 4-n-Butyl-l-(4-indophenyl)-3-methyl-2,6,7-trioxabicyclo-[2.2.2]octane, 4-n-Butyl--3-methyl-1-[4-(2-trimethylsilyl ethynyl)phenyl]-2,6,7-trioxabicyclo[2.2.2]octane, 4-n-Butyl-1-(4-ethynyl phenyl)-3-methyl-2,6,7- trioxabicyclo[2.2.2]octane, 4-t-Butyl-3-cyano-1-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]-octane, 1-(4-Bromophenyl)-3-cyano-4-n-propyl-2,6,7-trioxabicyclo-[2.2.2]octane, 3-Cyano-1-(4-iodophenyl)-4-n-propyl-2,6,7-trioxabicyclo-[2.2.2] octane, 3-Cyano-4-n-propyl-l-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2.2.2]octane, or 3-Cyano-l-(4-ethynylphenyl)-4-n-propyl-2,6,7- trioxabicyclo-[2.2.2]octane. 9) A process for the preparation of a compoundof the formula (I) as defined in any one of claims 1 to 8 which comprises the condensation of an orthocarboxylate of the formula R 2 C(OR 7 ) 3 with a trio; of the formula (II) wherein R to R 3 are as hereinbefore defined and R is C 1-4 alkyl, phenyl or C 7-8 aralkyl. 10) An insecticidal or acaricidal composition comprising a compound of formula (1) as defined in any one of claims 1-8 in admixture with a carrier or diluent. 11) A synergised pesticidal composition comprising a compound of formula (1), as defined in any one of claims 1-8,a synergist for the formula I compound and a carrier or diluent. 12) A mixture of a compound of formula (I) as defined in any one of claims 1-8 and another pesticidal compound. 13) A method for the control of pests comprising application to the pest or to an environment susceptible to pest infestation of a compound according to any one of claims 1-8 or a composition or mixture according to any one of claims 10-12. 14) A compound as defined in any one of claims 1-8 or composition according to any one of claims 10-12 for use in a method of surgery or therapy practised on the human or animal body or in a method of diagnosis practised on the human or animal body. wherein R, R 1 and R 3 are as defined in any one of claims 1-3, 6,7 or 8.