Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-02-20
2003-05-13
Stockton, Laura L. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S319500
Reexamination Certificate
active
06562853
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to ester compounds, methods of controlling a pest and uses of the ester compounds for controlling a pest.
BACKGROUND ART
U.S. Pat. No. 4,176,189 describes utilizing as an active ingredient of an acaricidal composition, certain compounds such as the compound encompassed by formula (A):
SUMMARY OF THE INVENTION
The present invention provides ester compounds, methods of controlling a pest and uses of the ester compounds. The ester compounds are encompassed by formula (1):
wherein, R represents a C1 to C3 alkyl group. The methods of controlling a pest comprise applying a pesticidally effective amount of an ester compound encompassed by formula (1) to at least one location selected from the pest and a habitat of the pest.
DETAILED DESCRIPTION OF THE INVENTION
The ester compounds encompassed by formula (1) can be designated as 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl 2,2-dimethyl-3-(alkenyl)cyclopropanecarboxylate compounds. In the present invention, there can be mentioned as the C1 to C3 alkyl group in formula (1), a methyl group, an ethyl group, a propyl group and an isopropyl group.
The ester compounds encompassed by formula (1) include various pesticidal isomeric forms thereof such as an optical isomer or a geometrical isomer form thereof. Examples of such isomers of the ester compounds encompassed by formula (1) include an optical isomer based on 2 asymmetric carbon atoms present in the cyclopropane ring moiety (R,S), a geometrical isomer based on the C═C double bond therein (E,Z) and the like. Further, the ester compounds encompassed by formula (1) include isomers that are both optical isomers and geometric isomers.
Examples of such isomers of the ester compounds encompassed by formula (1) include the ester compounds wherein in formula (1) the absolute configuration at the 1 position of the cyclopropane ring moiety is a R configuration; the ester compounds wherein in formula (1) the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a trans configuration; the ester compounds wherein in formula (1) the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a cis configuration; the ester compounds wherein in formula (1) the relative configuration of the C═C double bond at the 3 position of the cyclopropane ring moiety is a Z configuration; the ester compound wherein in formula (1) the absolute configuration at the 1 position of the cyclopropane ring moiety is a R configuration and the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a trans configuration; the ester compounds wherein in formula (1) the absolute configuration at the 1 position of the cyclopropane ring moiety is a R configuration and the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a cis configuration; the ester compounds wherein in formula (1) the absolute configuration at the 1 position of the cyclopropane ring moiety is a R configuration, the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a trans configuration and the relative configuration of the C═C double bond at the 3 position of the cyclopropane ring moiety is a Z configuration; and the ester compounds wherein in formula (1) the absolute configuration at the 1 position of the cyclopropane ring moiety is a R configuration, the relative configuration of the substituent at the 1 position of the cyclopropane ring moiety with the substituent at the 3 position of the cyclopropane ring moiety is a cis configuration and the relative configuration of the C═C double bond at the 3 position of the cyclopropane ring moiety is a Z configuration.
When controlling pests, it is preferred that there is utilized the ester compounds wherein in formula (1) the absolute configuration of the 1 position of the cyclopropane ring moiety is a R configuration. Alternatively, when controlling pests, it is preferred that there is utilized the ester compounds wherein in formula (1) R is a methyl group or ethyl group.
When utilizing a mixture of the isomers of the ester compounds to control pests, the mixture of he isomers thereof may contain at least 70% by moles, and preferably at least 80% by moles, of the ester compounds wherein in formula (1) the relative configuration of the C═C double bond at the 3 position of the cyclopropane ring is a Z configuration. Further, when controlling pests with a mixture of isomers of the ester compounds, it is preferred that the isomer mixture is abundant in the ester compound wherein in formula (1) the absolute configuration of the 1 position of the cyclopropane ring moiety is a R configuration.
The ester compound encompassed by formula (1) can be produced, for example, by the following production methods.
Production Method 1
Production method 1 is a method which has an alcohol compound encompassed by formula (2):
react with at least one of the carboxylic acid compounds encompassed by formula (3):
wherein R represents a C1-C3 alkyl group.
The reaction can be carried out by mixing together the alcohol compound encompassed by formula (2) with at least one of the carboxylic acid compounds encompassed by formula (3) in the presence of a condensing agent or acid catalyst, and usually in a solvent.
As examples of the condensing agent utilized in the reaction, there is mentioned dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the like. As the examples of the acid catalyst utilized in the reaction, there is mentioned inorganic acids such as sulfuric acid, organic acids such as paratoluene sulfonic acid and methane sulfonic acid and the like.
The solvent utilized in the reaction, is not particularly limited if inert in the reaction. As examples of such solvents, there is mentioned hydrocarbons such as toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane and 1,2 dichloroethane and the like and solvent mixtures thereof.
The reaction time for such a reaction is usually within a range of from immediately to 72 hours.
The reaction temperature for such a reaction is usually within a range of from −20° C. to 100° C. When utilizing the solvent, it is preferable to have the reaction temperature below the boiling point of the utilized solvent, particularly when the boiling point of the utilized solvent in the reaction is below 100° C.
The reaction may employ a molar ratio wherein, 1 mole of the alcohol compound encompassed by formula (2) maybe utilized for every 1 mole of said at least one of the carboxylic acid compounds encompassed by formula (3). However, it should be noted that the reaction may employ a molar ratio wherein 0.5 to 1.5 moles of the alcohol compound encompassed by formula (2) is utilized for every 1 mole of said at least one of the carboxylic acid compounds encompassed by formula (3).
In carrying out said reaction in the presence of the condensing agent, the amount of the condensing agent utilized in the reaction may change with the conditions of the reaction. Under typical conditions, the reaction usually employs a molar ratio wherein 1 mole of the condensing agent for every 1 mole of said at least one of the carboxylic acid compounds encompassed by formula (3).
Alternatively, when conducting said reaction in the presence of the acid catalyst, a catalytic amount of the acid catalyst be utilized in the reaction.
After the reaction, typical work-up procedures may be conducted with the reaction mixture, such as work-up procedures including pouring the reaction mixture into
Iwasaki Tomonori
Mori Tatsuya
Stockton Laura L.
Sumitomo Chemical Company Limited
LandOfFree
2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3049019