Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1997-08-22
2003-05-20
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C014S046000, C014S046000, C014S046000, C014S046000, C014S046000, C014S046000, C014S046000, C014S046000, C424SDIG001
Reexamination Certificate
active
06566388
ABSTRACT:
The present invention relates to an emulsifiable composition for the control of insects and a method of use thereof. The emulsifiable compositions of the present invention derive from 1-substituted phenyl pyrazoles insecticides and they do not favor the formation of crystals.
The 1-substituted phenyl pyrazoles insecticides can be liable to generate some crystallizations within the compositions during storage or use. When using such compounds for various applications, there may be problems of crystallization or recrystallization which prohibit a proper and easy application. This may happen in a quite different number of practical applications such as spray applications through a nozzle which may be clogged; dilution in a tank whereby the active ingredient may thus crystallize and fall at the bottom of the tank; application to animal's hair whereby the quality of the hair may be damaged by deposit of crystals thereon. For companion animals a most important requirement is to have a high quality hair, which is nice and pleasant when touching or petting.
Furthermore it is frequent that specialists in the control of insects, especially of termites, prepare a diluted pesticidal liquid the day before the application and utilize the remaining liquid the day after. These liquids, since they contain crystalline active ingredients, are poorly emulsified and are liable to crystallize in several hours after preparation of spraying emulsion, resulting in a great volume of liquid of no use or causing the clogging of pump nozzles employed for foam application.
In the particular situation of methods of control of insects, especially of termites, these methods may generally be divided into two main groups. On one side is the wood treatment according to which wooden parts of a house are subjected to pesticidal treatment and the other is called the soil treatment according to which a liquid pesticide is sprayed onto the underfloor area of a house. The application of a flowable formulation in which the active ingredient is suspended in water is becoming predominant, considering the health of the workers on an application within the limited space under the floor. However such dilution of water has the tendency to generate crystals. The conventional flowable formulation are not satisfactory.
Japanese Patent Publication No. 2-7282 has proposed to prevent the crystallization of some active ingredients which are not 1-substituted phenyl pyrazoles insecticides. Japanese Patent Application No. 50-69230 has described a liquid herbicidal composition containing as active ingredients thereof a dinitroaniline herbicide and a N-allyl-N′-alkoxy urea herbicide. It discloses also the use of an emulsifying agent and a solvent consisting of an alicyclic ketone in order to give to the composition the physical stability under the conditions of transportation, storage and end use.
An object of the present invention is to provide improved emulsifiable compositions which reduce the odor of the solvent(s) and/or prevent the crystallization of the 1-substituted phenyl pyrazoles insecticides upon dilution and/or are generally superior to the conventional flowable formulations.
The emulsifiable compositions of the present invention contain:
an insecticidally active ingredient which is a compound of formula (I), and
one, or more, weakly polar solvent, and
an emulsifying agent, and optionally
one, or more, further solvent(s).
Formula (I) for compounds used as active ingredient in the invention is
1-[4-R
1
2,6-(R
2
)
p
phenyl] 3-cyano 4-[R
4
—S(O)
n
] 5-R
5
pyrazole (I)
wherein:
R
1
is halogen, lower haloalkyl, lower haloalkoxy or SF
5
(lower being an integer from 1 to 4, preferably one),
R
2
is halogen, the various R
2
being identical or different,
R
4
is halogen, lower alkyl or haloalkyl,
R
5
is halogen, lower alkyl or amino,
n is 0 or 1 or 2; p is 0 or 1 or 2, preferably 2.
Halo before the name of a radical means that this radical may be substituted by one or more halogen atoms.
A preferred compound of formula (I) is compound 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole, hereinafter referred to as compound (A).
The compositions of the invention are useful for the treatment of many insects, especially termites, fleas, or arachnids such as ticks, and more generally insects on dogs or cats and other companion animals, as well as other insects as cited in European patent application 295117 which is herein incorporated by reference.
The compounds of formula (I) employed in the emulsifiable composition for the control of insects, especially of termites, of the present invention are known and described in the European patent application No. 295117 as well as in international patent applications WO 93/6089 and 94/21606. They are effective for the control of arthropods, plant nematodes, protozoan pests, insects, especially of termites, farm pests and the like.
Weakly polar solvents which may be used in the invention are generally those which have a dipolar moment positive, preferably higher than 1 (the unit is the debye) and a solubility in water (at 20° C.) of less than 10%. These weakly polar solvent(s) are preferably selected among the cyclic amides and the glycolic ether solvents.
Examples of cyclic amides which may be used are N-octyl-2-pyrrolidone, N-dodecyl-2-pyrrolidone and N-dodecyl-caprolactam.
Examples of weakly polar solvent(s) of the glycolic ether type are ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, ethylene glycol dibutyl ether, diethylene glycol dibutyl ether, propylene glycol monophenyl ether, dipropylene glycol monopropyl ether, ethylene glycol monobenzyl ether and the like. Preferred glycol solvent is diethylene glycol mono-2-ethylhexyl ether.
Emulsifing agents which may be used are preferably one or more of those selected from nonionic or anionic emulsifying agents. Examples of nonionic emulsifying agents which may be mentioned include: polyoxyalkylether, polyoxyethylenealkylphenylether, polyoxyethylenealkylether, polyethyleneglycol fatty ester, sorbitan fatty ester, polyoxyethylene sorbitan fatty ester, polyoxyethylenesorbit fatty ester, polyoxyethylenepolyoxy-propylenealkylether, polyoxyethylene (castor oil) ether. Examples of anionic emulsifying agents which may be mentioned include alkyl sulphates, polyxyethylenealkylether sulphates, sulfosuccinates, taurine derivatives, sarcosine derivatives, alkylbenzenesulfonates and the like. Preferred emulsifying agents are mixtures comprising of polyoxyethylene styrylphenylether and calcium alkylbenzenesulfonate (emulsifying agent a), and mixtures comprising of polyoxyethylene (castor oil) ether and calcium alkylbenzenesulfonate (emulsifying agent b).
Aromatic solvents may be used in the compositions of the present invention, generally to improve the solubility and/or the penetrability of the active ingredient. These aromatic solvent(s) are preferably selected from those being in liquid state at normal temperature (that is to say liquid at room temperature or at some temperature below 30° C.) and having a boiling point of at least 200° C. They may be more particularly selected from petroleum fraction, catalytic cracked oil fraction or synthetic oil and the like. Examples which may be mentioned include: mono- or poly-alkylbenzenes such as alkylbenzene or trimethylbenzene; naphthalenes such as methylnaphthalene, dimethylnaphthalene, dimethylmonopropylnaphthalene, dimethyldipropylnaphthalene or phenylxylylnaphthalene; alkyldiphenylalkanes such as 1-phenyl-1-xylylethane or alkyldiphenylethane; indene derivatives; dibenzylethers; diester phthalates and the like. 1-phenyl-1-xylylethane, dibenzyl ethers, dimethyl monopropyl naphthalene, dimethly dipropyl naphthalene are preferred.
If necessary, the composition of the present invention may contain a more polar solvent. Polar solvents which are not weakly polar solvents are generally those which have a dipolar moment positive, preferably higher than 1 (the unit is the d
Ikeda Michihiko
Kodama Hiroshi
Mizutani Takaaki
Shibayama Masakazu
Burns Doane Swecker & Mathis L.L.P.
Pak John
Rhone-Poulenc Agrochimie
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