Patent EP0162538A2 successfully refreshed from Google Patents.
EP0162538A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Cyclopropane derivates
Assignee: Imperial Chemical Industries Ltd
•
Filing: 1985-03-05
•
Granted: —
•
Expires: 2005-03-05
Abstract
Abstract Novel compounds are provided of formula I wherein: <CHEM> R<2> represents an alpha -branched alkyl group and R represents hydroxy halo or alkyl, useful as intermediates for the preparation of insecticidal compounds of formula I where R represents the residue of an alcohol, the ester of which the crysenthemic acid, permethrin acid or cyhalothrin acid has insecticidal properties.
Inventors
- 👤 Edward Mcdonald
- 👤 Roger Salmon
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 04:13
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; A; A01; A01N; A01N53/00; C07D239/28; C07D239/30; C07D401/00; C07D401/02; C07D401/12
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
67 words
A compound of formula : wherein R 2 represents an α-branched alkyl group containing from 3 to 6 carbon atoms, and R represents either (a) hydroxy, halo or alkoxy of up to six carbon atoms, or (b) the group -OR 1 where R is the residue of an alcohol of formula R 1 0H which forms an insecticidal ester with chrysanthemic acid, permethrin acid or cyhalothrin acid.
Claim 2
Dependent Claim
67 words
A compound of formula : wherein R 2 represents an α-branched alkyl group containing from 3 to 6 carbon atoms, and R represents either (a) hydroxy, halo or alkoxy of up to six carbon atoms, or (b) the group -OR 1 where R is the residue of an alcohol of formula R 1 0H which forms an insecticidal ester with chrysanthemic acid, permethrin acid or cyhalothrin acid.
Claim 3
Dependent Claim
130 words
A compound according to claim 1 wherein R 2 represents an α-branched alkyl group containing from 3 to 6 carbon atoms and R represents a group of formula : wherein X is oxygen, sulphur, vinylene or a group of formula -CR 5 =Y- where Y is nitrogen or CR 5 , R 4 is hydrogen, methyl, cyano or ethynyl, each R 5 is selected from hydrogen, halogen and alkyl of up to 4 carbon atoms optionally substituted with halogen, n is two, and R 6 is hydrogen, halogen, alkyl of up to 4 carbon atoms, alkenyl of up to 6 carbonatoms, phenyl, phenoxy or benzyl, or phenyl, phenoxy or benzyl substituted with halogen or alkyl, provided that R 4 is hydrogen when R 6 is hydrogen, halogen, alkyl or alkenyl.
Claim 4
Dependent Claim
21 words
A compound according to claim 2 wherein R 2 is selected from prop-2-yl, but-2-yl, pent-2-yl, pent-3-yl, 2-methylprop-2-yl, 2-methylbut-2-yl, cyclopropyl and cyclohexyl.
Claim 5
Dependent Claim
24 words
A compound according to claim 2 where R represents pentafluorobenzyloxy, 4-methyl-2,3,5,6-tetrafluoro- benzyloxy, 4-allyl-2,3,5,6-tetrafluorobenzyloxy, 4-methoxymethyl-2,3,5,6-tetrafluorobenzyloxy, 3-phenoxybenzyloxy, α-cyano-3-phenoxybenzyloxy, 4-fluoro-3-phenoxybenzyloxy, α-cyano-4-fluoro-3-phenoxybenzyloxy, α-ethynyl-3-phenoxybenzyloxy, 2-methyl-3-phenylbenzyl, 6-phenoxypyrid-2-ylmethanol, 1-cyano-1-(6-phenoxypyrid-2-yl)methanol, or 1-(6-phenoxypyrid-2-yl)ethanol.
Claim 6
Dependent Claim
5 words
The compound α-cyano-3-phenoxybenzyl trans-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate.
Claim 7
Dependent Claim
5 words
The compound α-cyano-3-phenoxybenzyl trans-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate.
Claim 8
Dependent Claim
24 words
The compound of claim 5 in the form of the enantiomeric pair of isomers represented by (S)-α-cyano-3-phenoxybenzyl (lR,trans)-3-E2-(2-methyl- prop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate and (R)-α-cyano-3-phenoxybenzyl (1S,trans)-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate.
Claim 9
Dependent Claim
5 words
The compound l-cyano-l-(6-phenoxypyrid-2-yl)methyl trans-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate.
Claim 10
Dependent Claim
5 words
The compound l-cyano-l-(6-phenoxypyrid-2-yl)methyl trans-3-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-2,2-dimethylcyclopropane carboxylate.
Claim 11
Dependent Claim
34 words
An insecticidal and acaricidal composition comprising as active ingredient a compound according to claim 1 wherein R represents a group OR 1 , in association with a diluent or carrier for the active ingredient.
Claim 12
Dependent Claim
29 words
A method of combating insect and acarine pests at a locus which comprises treating the locus with an insecticidally and acaricidally effective amount of the composition of claim 8.
Claim 13
Dependent Claim
231 words
A process for preparing a compound of claim 1 wherein either (a) an acid of formula where Q represents the hydroxy group and R 2 has any of the meanings given hereinabove, may be reacted directly with an alcohol of formula R 1- OH (III) where R 1 has any of the meanings given in claim 1 the reaction taking place in the presence of an acid catalyst, or a dehydrating agent, or (b) an acid halide of formula II where Q represents a halogen atom, preferably a chlorine atom, and R 2 has any of the meanings given in claim 1, may be reacted with an alcohol of formula III, the reaction taking place in the presence of a base, or (c) an acid of formula II where Q represents the hydroxy group or an alkali metal salt thereof, may be reacted with halide of formula Q 1- R 1 (IV) wherein Q 1 represents a halogen atom, and R 1 has any of the meanings given in claim 1 or with the quaternary ammonium salts derived from such halides with tertiary amines, or (d) a lower alkyl ester of formula (II) where Q represents a lower alkoxy group containing up to six carbon atoms, and R 2 has any of the meanings given in claim 1, is heated with an alcohol of formula III to effect a transesterification reaction.
Claim 14
Dependent Claim
43 words
A compound of formula : wherein Z is bromo, formyl or a group of formula wherein R 9 is an akyl group of up to 6 carbon atoms, and R 2 is an α-branched alkyl group of from 3 to 6 carbon atoms.
Claim 15
Dependent Claim
43 words
A compound of formula : wherein Z is bromo, formyl or a group of formula wherein R 9 is an akyl group of up to 6 carbon atoms, and R 2 is an α-branched alkyl group of from 3 to 6 carbon atoms.
Claim 16
Dependent Claim
26 words
A conpound of formula : wherein R is alkoxy of up to 6 carbon atoms and R 7 is alkyl of up to 6 carbon atoms.
Claim 17
Dependent Claim
26 words
A conpound of formula : wherein R is alkoxy of up to 6 carbon atoms and R 7 is alkyl of up to 6 carbon atoms.
Claim 18
Dependent Claim
34 words
A compound of formula : wherein G is either OR 7 where R 7 is alkyl of up to 6 carbon atoms or dimethylamino and R is alkoxy of up to 6 carbon atoms.
Claim 19
Dependent Claim
34 words
A compound of formula : wherein G is either OR 7 where R 7 is alkyl of up to 6 carbon atoms or dimethylamino and R is alkoxy of up to 6 carbon atoms.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.