Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Fungus – except allergen – or component thereof or substance...
Patent
1981-12-04
1984-07-10
Torrence, Dolph H.
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Fungus, except allergen, or component thereof or substance...
260465D, 548479, 548530, 549 58, 549 79, 549469, 549488, 424275, 424285, 424304, 424305, 560124, A01N 5300, C07C 6974, C07C12175, C07D20948
Patent
active
044593058
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to novel cyclopropanecarboxylic acid ester derivatives having the action of killing insects and ticks, a method of manufacturing those derivatives, and an insecticide and acaricide containing such a derivative as its active ingredient.
BACKGROUND ART
In esters of chrysanthemumic acid which are known as insecticides, various kinds of alcohol components have been studied, and the esters employing such alcohols have been put to practical use. These crysanthemumic esters are, however, liable to be decomposed through oxidation upon exposure to light, and their outdoor use is, therefore, limited. Much recent research has been directed to the acid components of those esters. As a result, there are known compounds which are more stable against light than pyrethroid, for example, esters of dihalovinylcrysanthemumic acid of the formula (X) with halogen atoms substituted for methyl groups: ##STR3## in which X stands for a halogen atom, and esters of tetramethylcyclopropanecarboxylic acid of the formula XI: ##STR4##
The esters of the acid represented by the formula XI have difficulties unsolved in practical use, since it is inferior in insecticidal activity to the esters of chrysanthemumic acid or those of the acids of the formula X, and higher in toxicity to men and cattle. The esters of the acids of the formula X are not always acceptable, either, in view of the problems of environmental pollution, chromic toxicity, etc.
As a result of strenuous researches, the inventors of this invention have discovered that if some of its methyl groups are replaced by halogen atoms or halomethyl groups, the esters of the acid represented by the formula XI surprisingly have remarkably improved insecticidal activities and largely reduced toxicities. The esters of the novel cyclopropanecarboxylic acids compared with the esters of the non-replaced acid exhibit far higher stabilities against light than the known chrysanthemumic acid esters.
The present invention has been accomplished on the basis of the above-mentioned knowledge.
DISCLOSURE OF THE INVENTION
This invention relates to novel cyclopropanecarboxylic acid ester derivatives of the general formula I: ##STR5## in which R.sub.1 stands for a hydrogen atom, a methyl group, a halogen atom, or a halomethyl group, R.sub.1 ' stands for a halomethyl or haloethyl group, R.sub.2 and R.sub.2 ' are the same or different, each standing for any one of a methyl group, a halogen atom, and a halomethyl group, provided that if R.sub.1 is a hydrogen atom, R.sub.1 ' is a halomethyl group, and R.sub.2 and R.sub.2 ' are each a methyl group, and R stands for a group of the formula II, III, IV, V or VI: ##STR6## in which R.sub.3 stands for a hydrogen atom or a methyl group, R.sub.4 stands for an allyl, propargyl, benzyl or 2,4-pentadienyl group, X stands for an oxygen or sulfur atom, or a --CH.dbd.CH-- group, R.sub.5 stands for a hydrogen atom or a cyano, ethynyl, propynyl or trifluoromethyl group, R.sub.6 stands for a hydrogen atom, a methyl group, a halogen atom or a trifluoromethyl group, n is an integer of 1 to 4, R.sub.7 stands for a halogen atom, a lower alkyl, lower haloalkoxy or lower haloalkoxymethyl group, an allyl, propargyl, benzyl, benzoyl or phenoxy group, a phenoxy group having one hydrogen atom in the benzene ring replaced by a halogen atom, a methyl or lower alkoxy group, or a dichlorovinyloxy group, R.sub.5 and R.sub.6 may have their ends bonded to each other to form an ethylene or methyleneoxy chain, and R.sub.6 and R.sub.7 may have their ends bonded to each other to form a trimethylene or tetramethylene chain, R.sub.8 stands for a hydrogen atom or an ethynyl group, R.sub.9 and R.sub.9 ' stand for a hydrogen atom, a methyl group or a halogen atom, R.sub.10 stands for a phenyl or benzyl group, or an alkyl, alkenyl or alkynyl group having 2 to 4 carbon atoms, R.sub.11 stands for a tetrahydrophthalimide or dialkylmaleimide group, and R.sub.12 stands for a phenyl or phenoxy group, and the optical or geometrical isomer thereof. The invention
REFERENCES:
patent: 4279835 (1981-06-01), Martel et al.
patent: 4299839 (1981-11-01), Omura et al.
Katsuda Yoshio
Minamite Yoshihiro
Dainippon Sochugiku Kabushiki Kaisha
Torrence Dolph H.
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