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A class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)octanes

Assignee: University of California Berkeley
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Filing: 1985-01-30
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Granted: —
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Expires: 2005-01-30
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Abstract

Abstract A pesticidal composition comprising a compound having the formula R-C(CH 2 O) 3 C-X wherein R and X are each organic substituents and wherein the compound has an LD 50 , in micrograms of compound per gram of body weight of Musca domestica, of less than about 400 and or an LD 50 in the presence of synergist of less than about 60 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.

Inventors

  • 👤 John E. Casida
  • 👤 Christopher J. Palmer

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-30 10:40
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A01; A01N; A01N43/00; A01N43/90

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 42 words
A compound R-C(CH 2 0) 3 C-X wherein R and X are each organic substituents, the compound exhibiting an LD 50 for pesticidal activity, in micrograms of compound per gram of body weight of Musca domestica of no more than about 400.
Claim 2
Dependent Claim 42 words
A compound R-C(CH 2 0) 3 C-X wherein R and X are each organic substituents, the compound exhibiting an LD 50 for pesticidal activity, in micrograms of compound per gram of body weight of Musca domestica of no more than about 400.
Claim 3
Dependent Claim 33 words
A compound as defined in claim 1 in admixture with a synergist, the combination exhibiting an LD 50 for pesticidal activity against Musca domestica of no more than about 60 micrograms per aram.
Claim 4
Dependent Claim 43 words
A compound R-C(CH 2 O) 3 C-X wherein R is propyl, butyl, C 3-10 cycloalkyl or phenyl and X is C 6-10 cycloalkyl, C 6-10 cycloalkenyl, alkynyl or substituted phenyl, as hereinbefore defined, provided that R is not phenyl when X is 4-fluorophenyl.
Claim 5
Dependent Claim 43 words
A compound R-C(CH 2 O) 3 C-X wherein R is propyl, butyl, C 3-10 cycloalkyl or phenyl and X is C 6-10 cycloalkyl, C 6-10 cycloalkenyl, alkynyl or substituted phenyl, as hereinbefore defined, provided that R is not phenyl when X is 4-fluorophenyl.
Claim 6
Dependent Claim 58 words
A compound according to claim 3 wherein R is propyl, butyl, C 5-6 cycloalkyl or phenyl and X is cyclohexyl, cycloheptyl, cyclohexenyl, ethynyl or phenyl substituted by halo, cyano, azido, nitro or C l-2 alkyl, the said C l-2 alkyl being substituted by 1 to 3 halogen atoms, provided that R is not phenyl when X is 4-fluorophenyl.
Claim 7
Dependent Claim 41 words
A compound according to either claim 3 or 4 wherein R is n-propyl, butyl, cyclopentyl or cyclohexyl and X is cyclohexyl, cycloheptyl, or phenyl substituted in the 3- and/or 4- position by substituents independently selected from halo, cyano, azido and nitro.
Claim 8
Dependent Claim 33 words
A compound according to either claim 3 or 4 wherein R is phenyl and X is phenyl substituted in the 3- and/or 4- positions by a substituent independently selected from chloro and bromo.
Claim 9
Dependent Claim 33 words
A compound selected from the group consisting of l-(4-chlorophenyl)-4-n-propyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-n-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-s-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-chlorophenyl)-4-t-butyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-cyclopentyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-chlorophenyl)-4-phenyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-cyclohexyl-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cycloheptyl-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-fluorophenyl}-4-t-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-bromophenyl)-4-t-butyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-nitrophenyl)-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-cyanophenyl)-4-t-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(3,4-dichlorophenyl)-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cyclohexyl-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cycloheptyl-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane,'1-(4-fluorophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-bromophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-cyanophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, and 1-(3,4-dichlorophenyl)-4-cyclohexyl-2,6,7- trioxabicyclo[2.2.2]octane.
Claim 10
Dependent Claim 33 words
A compound selected from the group consisting of l-(4-chlorophenyl)-4-n-propyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-n-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-s-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-chlorophenyl)-4-t-butyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-cyclopentyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-chlorophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-chlorophenyl)-4-phenyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-cyclohexyl-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cycloheptyl-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-fluorophenyl}-4-t-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-bromophenyl)-4-t-butyl-2,6,7- trioxabicyclo[2.2.2]octane, 1-(4-nitrophenyl)-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-cyanophenyl)-4-t-butyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(3,4-dichlorophenyl)-4-t-butyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cyclohexyl-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-cycloheptyl-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane,'1-(4-fluorophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, 1-(4-bromophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo-[2.2.2]octane, 1-(4-cyanophenyl)-4-cyclohexyl-2,6,7-trioxabicyclo[2.2.2]octane, and 1-(3,4-dichlorophenyl)-4-cyclohexyl-2,6,7- trioxabicyclo[2.2.2]octane.
Claim 11
Dependent Claim 22 words
A pesticidal composition comprising a compound according to any of claims 1 to 4 and 7 in admixture with an inert carrier.
Claim 12
Dependent Claim 15 words
A pesticidal composition according to claim 8 which further comprises a synergist as hereinbefore defined.
Claim 13
Dependent Claim 18 words
A compound as defined in any of claims 1 to 4 and 7 for the control of pests.
Claim 14
Independent Claim 40 words
A method of controlling pests comprising contacting said pests or their environment with an effective amount for controlling said pests of a compound R-C(CH 2 0) 3 C-X as defined in any one of claims 1 to 4 and 7.
Claim 15
Dependent Claim 24 words
A method of controlling insects according to claim 11 wherein said pests or their environment are also contacted with a synergist as hereinbefore defined.
Claim 16
Independent Claim 72 words
A method of preparing a compound R-C(CH 2 O) 3 C-X according to any one of claims 1 and 3 to 7: a) from a triol R-C(CH 2 OH) 3 which comprises acid catalysed condensation of the triol with an orthocarboxylate (R'O) 3 C-X or b) by the rearrangement of an acylated hydroxymethyloxetane wherein R and X are as defined in relation to any one of claims 1 and 3 to 7.

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