Ester compounds

Details Ester compounds Ester compounds

1999-02-24

2001-05-01

Killos, Paul J. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C514S531000

Reexamination Certificate

active

06225495

ABSTRACT:

The present invention relates to ester compounds and pesticides containing thereof as an active ingredient.
Japanese Patent Publications describe some ester compounds such as (4-allylphenyl)methyl 1RS-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate in JP-sho-47-43333A and (2,3,5,6-tetrafluorophenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate in JP-hei-5-32509A. However, these ester compounds are not satisfactorily effective. The problem of the present invention is to provide a compound having an excellent pesticidal activity.
The present invention provides an ester compound (hereinafter referred to as “the present compound”) shown by the formula (I):
wherein R
1
represents a hydrogen atom, halogen atom, C
1
-C
3
alkyl group optionally substituted by halogen atom(s), C
2
-C
3
alkenyl group optionally substituted by halogen atom(s), C
1
-C
3
alkoxy group optionally substituted by halogen atom(s), C
1
-C
3
alkylthio group optionally substituted by halogen atom(s) or (C
1
-C
3
alkoxy)methyl group optionally substituted by halogen atom(s), n represents an integer of 1 to 4 and X represents a hydrogen atom or C
1
-C
3
alkyl group, and a pesticide containing thereof as an active ingredient.
The halogen atoms in the present invention are exemplified by a fluorine atom, chlorine atom, bromine atom; the C
1
-C
3
alkyl group optionally substituted by halogen atom(s) is exemplified by a methyl group, ethyl group, trifluoromethyl group; the C
2
-C
3
alkenyl group optionally substituted by halogen atom(s) is exemplified by an allyl group, 2,2-dichlorovinyl group; the C
1
-C
3
alkoxy group optionally substituted by halogen atom(s) is exemplified by a methoxy group, trifluoromethoxy group; the C
1
-C
3
alkylthio group optionally substituted by halogen atom(s) is exemplified by a methylthio group; and the (C
1
-C
3
alkoxy)methyl group optionally substituted by halogen atom(s) is exemplified by a methoxymethyl group.
The present compounds can be produced by the following methods.
(Method A)
The method for producing the present compound by reacting the carboxylic acid compound shown by the formula (II):
wherein X has the same meaning defined above, or its reactive derivative, with the alcohol compound shown by the formula (III):
wherein R
1
and n have the same meanings defined above, or its reactive derivative.
The reaction is usually carried out in an organic solvent. It may be done in the presence of a condensing agent or while removing by-products from the reaction system if necessary.
The reaction time is usually within a range between 5 minutes and 72 hours and the reaction temperature is usually within a range between −80° C. and the boiling point of the solvent used in the reaction or up to 200° C.
The reactive derivatives of the carboxylic acid compounds shown by the formula (II) are exemplified by acid halides, acid anhydrides, C
1
-C
4
alkyl esters.
The reactive derivatives of the alcohol compounds shown by the formula (III) are exemplified by halides, sulfonate esters, quarternary ammonium salts.
The molar ratio of the carboxylic acid compound shown by the formula (II) or its reactive derivative to the alcohol compound shown by the formula (III) or its reactive derivative can be optionally set and it is preferably equimolecular amount or nearby.
The examples of the condensing agents include organic bases such as tertiary amines (triethylamine, 4-dimethyaminopyridine, diisopropylethylamine and the like), nitrogen-containing aromatic compounds (pyridine and the like), alkali metal alkoxides (sodium methoxide, potassium tert-butoxide and the like); inorganic bases such as sodium hydroxide, potassium carbonate; Lewis acids such as titanium (IV) phenoxide, proton acids (e.g. p-toluenesulfonic acid, sulfuric acid), etc.; dicyclohexylcarbodiimide; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; diethyl azodicarboxylatetriphenylphosphine.
These condensing agents are suitably selected according to the kind of the carboxylic acid compounds shown by the formula (II) or its reactive derivatives or the kind of the alcohol compounds shown by the formula (III) or its reactive derivatives. The amount of the reagents are suitably selected according to the type of the reaction.
Examples of the solvent include hydrocarbons such as benzene, toluene, hexane and the like; ethers such as diethyl ether, tetrahydrofuran and the like; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and the like; amides such as dimethylformamide and the like; and ketones such as acetone and the like.
After the completion of the reaction, the reaction solution can be subjected to a usual work-up treatment such as extraction with organic solvent, concentration, and so on to give the present compound. If necessary, it may be purified by usual procedure such as chromatography, distillation, recrystallization and/or the like.
The carboxylic acid compounds shown by the formula (II) or its reactive derivatives can be prepared according to the methods described in J. Chem. Soc. 1076 (1970), JP-sho-47-43333A or JP-sho-49-47531A. The alcohol compounds shown by the formula (III) or its reactive derivatives can be prepared according to the methods described in JP-sho-57-123146A, JP-sho-53-79845A or JP-sho-56-97251A.
(Method B)
The method for producing the present compound by reacting the aldehyde compound shown by the formula (IV):
wherein R
1
and n have the same meanings defined above, with the phosphorane compound shown by the formula (V):
wherein X has the same meaning defined above and Z
1
, Z
2
and Z
3
are the same or different and represent C
1
-C
8
alkyl group or optionally substituted phenyl group.
The reaction is usually carried out in a solvent. The reaction time is usually within a range between 5 minutes and 72 hours and the reaction temperature is usually within a range between −80° C. and the boiling point of the solvent used in the reaction or up to 100° C.
Examples of the solvent include hydrocarbons such as benzene, toluene, hexane and the like; ethers such as diethyl ether, tetrahydrofuran and the like; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and the like; amides such as dimethylformamide and the like; and alcohols such as methanol and the like.
The amount of the phosphorane compound shown by the formula (V) used in the reaction is usually from 1 mole to an excess, preferably from 1 mole to 5 moles based on 1 mole of the aldehyde compound shown by the formula (IV).
After the completion of the reaction, the reaction solution can be subjected to a usual work-up treatment such as filtration, extraction with organic solvent, concentration, and so on to give the present compound. If necessary, it may be purified by usual procedure such as chromatography, distillation, recrystallization and/or the like.
The aldehyde compound shown by the formula (IV) can be prepared according to the method described in JP-sho-49-47531A and the phosphorane compound shown by the formula (V) can be prepared according to the method described in “Jikkenkagakukoza” (Experimental Chemistry Course) (4th ed., Maruzen Co.) vol. 19, 59.
The present compounds have optical isomers (R, S) based on an asymmetric carbon, geometrical isomers (E, Z) based on a double bond and geometrical isomers (cis, trans) based on a cyclopropane ring. The present invention includes all the optical isomers, geometrical isomers and their mixtures having pesticidal activity.
Examples of the carboxylic acid compounds shown by the formula (II) include the followings:
2,2-dimethyl-3-vinylcyclopropanecarboxlic acid
2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxlic acid
3-(1-butenyl)-2,2-dimethylcyclopropanecarboxlic acid
Examples of the alcohol compounds shown by the formula (III) include the followings:
(2,3,5,6-tetrafluorophenyl)methanol
(2,3,5,6-tetrafluoro-4-methylphenyl)methanol
(2,3,5,6-tetrafluoro-4-methoxyphenyl)methanol
(2,3,4,5,6-pentafluorophenyl)methanol
Examples of the aldehyde compounds shown by the formula (IV) include the fol

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