University of California

Other

Roussel Uclaf

Christopher J Palmer

John E Casida

John P Larkin

Ian H Smith

John B Weston

Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2,]-octanes and bicyclo-[2,2,3]-nonanes having 2 or 3 ring hetero atoms selected from O, S and N, substituted at the 1-position by a 4-alkynylphenyl group and at the 4-position and optionally at the 3 and/or 5-position are valuable pesticides, particularly insecticides and acaracides. The compounds may be prepared by reacting an alkyne with the corresponding 4-iodophenyl substituted compound or by debromination of the corresponding 4-dibromomethylphenyl substituted compound.

Trithiabicyclo[2,2,2]octanes

The present invention provides compounds of the formula (I): ##STR1## wherein R is a phenyl group, substituted fluorine atoms formulations containing them and their use in controlling pest infestation.

Pesticidal compounds

Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo-[2,2,3]-nonanes having 2 or 3 ring hetero atoms selected from O, S and N, substituted at the 1-position by a 4-alkynylphenyl group and at the 4-position and optionally at the 3 and/or 5-position are valuable pesticides, particularly insecticides and acaracides. The compounds may be prepared by reacting an alkyne with the corresponding 4-iodophenyl substituted compound or by debromination of the corresponding 4-dibromomethylphenyl substituted compound.

Pesticidally-active alkynylphenyl-substituted 1,3-oxathianes and related substituted compounds of the formula: ##STR1## and their use in controlling pests such as arthropods and helminths are described.

Alkynylphenyl-substituted 1,3-oxathione compounds with pesticidal

Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo[2,2,3]-nonanes having 2 or 3 ring hetero atoms selected from O, S and N, substituted at the 1-position by a 4-alkynylphenyl group and at the 4-position and optionally at the 3 and/or 5-position are valuable pesticides, particularly insecticides and acaracides. The compounds may be prepared by reacting an alkyne with the corresponding 4-iodophenyl substituted compound or by debromination of the corresponding 4-dibromomethylphenyl substituted compound.

Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo-[2,2,3]-nonanes, having 2 or 3 ring hetero atoms selected from O, S and N, substituted at the 1-position by a 4-alkynylphenyl group and at the 4-position and optionally at the 3 and/or 5-position are valuable pesticides, particularly insecticides and acaracides. The compounds may be prepared by reacting an alkyne with the corresponding 4-iodophenyl substituted compounds or by debromination of the corresponding 4-dibromomethylphenyl substituted compound.

The present invention relates to a compound of the formula (I): ##STR1## wherein R is C.sub.2-10 alkyl, alkenyl or alkynyl, each optionally substituted by or methyl substituted by cyano, C.sub.3-4 cycloalkyl, halo, C.sub.1-4 alkoxy or a group S(O)m R.sup.4 where R.sup.4 is C.sub.1-4 alkyl and m is 0, 1 or 2, or Ris C.sub.3-10 cycloalkyl, C.sub.4-10 cycloalkenyl or phenyl, each optionally substituted by C.sub.1-4 alkoxy, C.sub.1-3 alkyl, C.sub.2-4 alkynyl, halo, cyano or a group S(O)m R.sup.4 as defined hereinbefore; R.sup.1 is halo, C.sub.1-3 alkyl, C.sub.2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C.sub.1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R.sup.4 as defined hereinbefore or alkynyl substituted by tri-C.sub.1-4 alkylsilyl, or R.sup.1 is cyano, spiro-cyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano of C.sub.1-3 alkyl optionally substituted by fluorine, or R.sup.1 and R and the carbon atoms to which they are attached form a C.sub.5-7 carbocyclic ring optionally substituted by halo, C.sub.1-3 alkyl or alkoxy or C.sub.2-3 alkenyl, R.sup.2 is phenyl substituted by an C.sub.2-3 alkynyl group or by a tri-C.sub.1-4 alkylsilylalkynyl group and R.sup.3 is hydrogen, C.sub.1-3 alkyl, C.sub.2-3 alkenyl or alkynyl each optionally substituted by cyano, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy or halo, or R.sup.3 is cyano or halo, its use in medicine, pharmaceutical compositions containing it and its preparation.

A pesticidal composition comprising a compound having the formula R--C(CH.sub.2 O).sub.3 C--X wherein R and X are each organic substituents and wherein the compound has an LD.sub.50, in micrograms of compound per gram of body weight of a selected pest, of less than about 400 and/or an LD.sub.50 in the presence of synergist of less than about 20 is disclosed along with its use in killing pests. Pesticidal activity has been found against a broad range of types of insects. The pesticidal activity of the composition is strongly enhanced by the use of a selected synergist.

New class of pesticides comprising

A compound of the formula ##STR1## wherein R is C.sub.3 -C.sub.10 normal- or branched- alkyl or cycloalkyl, C.sub.3 -C.sub.10 normal- or branched- alkyl or cycloalkyl having one or more halogen, cyano, C.sub.1 -C.sub.2 partially or completely halogenated alkyl, or C.sub.1 -C.sub.3 alkoxy or partially or completely halogenated alkoxy substituents, C.sub.3 -C.sub.10 cycloalkyl having C.sub.1 -C.sub.2 alkyl substituents, phenyl, or phenyl having one or more halogen, cyano, nitro, ethynl, C.sub.1 -C.sub.2 alkyl or partially or completely halogenated alkyl, or C.sub.1 -C.sub.3 alkoxy or partially or completely halogenated alkoxy substituents; wherein at least one of R.sub.2 -R.sub.6 is ethynyl; and wherein the remainder of R.sub.2 -R.sub.6 are independently either hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, partially or completely halogenated C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.3 alkoxy, partially or completely halogenated C.sub.1 -C.sub.3 alkoxy, ethynyl, nitro, cyano, or azido. Such a compound is useful in killing pests, particularly insects.

Growing community of inventors

Ipswich, United Kingdom

Christopher J Palmer