Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
1999-05-28
2001-01-23
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S345000
Reexamination Certificate
active
06177412
ABSTRACT:
FIELD OF THE INVENTION
The present invention is directed to an insecticidal composition and to a method for the use thereof. In particular, the present invention is directed to an insecticidal composition which takes advantage of the synergistic action of two particular insecticides and to a method of using the composition to kill insects such as the tobacco budworm and other Lepidopteran pests of cotton.
BACKGROUND OF THE INVENTION
The tobacco budworm and other Lepidopteran insects are serious pests of cotton fruit (squares and bolls). Moderate or heavy infestations can dramatically reduce lint yields.
The tobacco budworm,
Heliothis virescens
, and cotton bollworm,
Helicoverpa zea
, have developed resistance to major classes of insecticides used to control them, as discussed in Martin et al., “Effects of Selected Synergists on Insecticide Toxicity in Tobacco Budworm (Lepidoptera: Noctuidae) in Laboratory and Field Studies,” J. Econ. Entomol. 90(3)723-731 (1997), Kanga et al., “Tolerance to Cypermethrin and Endosulfan in Field Populations of the Bollworm (Lepidoptera: Noctuidae) from Texas,” J. Econ. Entomol. 89(3)583-589 (1996), Kanga et al., “Monitoring for Resistance to Organophosphorus, Carbamate, and Cyclodiene Insecticides in Tobacco Budworm Adults (Lepidopteria: Noctuidae),” J. Econ. Entomol. 88(5)1144-1149 (1995), and Elzen et al., “Resistance to Pyrethroids, Carbamate, and Organophosphate Insecticides in Field Populations of Tobacco Budworms (Lepidoptera: Noctuidae) in 1990,” J. Econ. Entomol. 85(6):2064-2072 (1992).
New and better control alternatives are always needed to maintain crop production and provide alternative chemistry for rotation purposes, as discussed in Laws, Delta Agricultural Digest, Intertec Publishing (1998).
While the compositions in the art have provided some control of Lepidopteran pests of cotton, there has been a need in the art for significantly greater control.
SUMMARY OF THE INVENTION
An object of the present invention is to provide significantly greater control of tobacco budworm, cotton bollworm, and other Lepidopteran pests of cotton than has been provided previously in the art.
Accordingly, the present inventors conducted extensive experimentation and, as a result, they achieved the present invention, which provides a novel and highly effective, multi-chemistry alternative that provides synergistic results for the control of Lepidopteran insects on cotton and other crops on which they might be present.
In particular, the present invention is directed to an insecticidal composition comprising (1) at least one compound of formula (I):
wherein R, is bromine, chlorine, methyl, or ethyl, R
2
is bromine, chlorine, or ethyl, R
3
is hydrogen, halogen, or trifluoromethyl, X is —O—, —S—, or —NH—, and n is 2, 3, or 4, and (2) at least one compound of formula (II):
wherein R and R
1
independently are an alkyl, alkenyl, or alkynyl group containing up to 6 carbon atoms, R
2
is hydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to 8 carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, R
3
is hydrogen or an alkyl group containing 1 to 6 carbon atoms, and Y is —O— or —S—.
Also, the present invention is directed to a method of killing Lepidopteran insects comprising applying to an area to be treated an insecticidally effective amount of a composition comprising (1) at least one compound of formula (I):
wherein R
1
is bromine, chlorine, methyl, or ethyl, R
2
is bromine, chlorine, or ethyl, R
3
is hydrogen, halogen, or trifluoromethyl, X is —O—, —S—, or —NH—, and n is 2, 3, or 4, and (2) at least one compound of formula (II):
wherein R and R
1
independently are an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms, R
2
is hydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to 8 carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, R
3
is hydrogen or an alkyl group containing 1 to 6 carbon atoms, and Y is —O— or —S—.
DETAILED DESCRIPTION OF THE INVENTION
One component of the composition of the present invention is a compound of formula (I):
where R
1
is bromine, chlorine, methyl, or ethyl, R
2
is bromine, chlorine, 15 or ethyl, R
3
is hydrogen, halogen, or trifluoromethyl, X is —O—, —S—, or —NH—, and n is 2, 3, or 4. This compound and methods for its preparation are described in detail in WO 96/11909, which is incorporated herein by reference.
A particularly preferred compound within formula (I) is one in which R
1
is chlorine, R
2
is chlorine, R
3
is hydrogen, X is —O—, and n is 3, i.e., 2-[3-[2,6-dichloro-4-(3,3-dichloroprop-2-enyloxy)phenoxy]propoxy]-5-(trifluoromethyl)pyridine (which has been revised from 3,5-dichloro-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene).
A compound of formula (I) can be prepared by the following method.
A compound of formula (a)
wherein R
1
is bromine, chlorine, methyl, or ethyl, R
2
is bromine, chlorine, or ethyl, X is —O—, —S—, or —NH—, and n is 2, 3, or 4, is reacted with a compound of formula (b)
where R
3
is hydrogen, halogen, or trifluoromethyl and L is halogen (e.g., chlorine, bromine, or iodine), mesyloxy, or tosyloxy.
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C
1
-C
4
) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C
1
-C
4
) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of formula (a).
The reaction temperature is usually set within the range of −20° C. to 150° C. or the boiling point of a solvent used in the reaction, preferably −5° C. to 100° C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallation.
Another component of the composition of the present invention s a compound of formula (II):
wherein R and R
1
independently are an alkyl, alkenyl, or alkynyl group containing up to 6 carbon atoms, R
2
is hydrogen, an alkyl group containing 1 to 18 carbon atoms, a cycloalkyl group containing 3 to 8 carbon atoms, an alkenyl group containing 2 to 18 carbon atoms, or an alkynyl group containing 3 to 18 carbon atoms, R
3
is hydrogen or an alkyl group containing 1 to 6 carbon at
East David
Kincade Robert T.
Robinson Allen J.
Sughrue Mion Zinn Macpeak & Seas, PLLC
Valent U.S.A. Corporation
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