AU2005215927B2 - Pesticidal emulsifiable concentrate - Google Patents

Description

AUSTRALIA PATENTS ACT 1990 COMPLETE SPECIFICATION NAME OF APPLICANT(S):: Sumitomo Chemical Company, Limited ADDRESS FOR SERVICE: DAVIES COLLISON CAVE Patent Attorneys I Nicholson Street, Melbourne, 3000, Australia INVENTION TITLE: Pesticidal emulsifiable concentrate The following statement is a full description of this invention, including the best method of performing it known to me/us: 5102 la FIEDL OF THE INVENTION The present invention relates to a pesticidal 5 emulsifiable concentrate. More specifically, it relates to a pesticidal emulsifiable concentrate comprising pyridalyl as an effective ingredient. BACKGROUND OF THE INVENTION 10 Pyridalyl, i.e., 2, 6-dichloro-4-

(

3 , 3 dichloroallyloxy)phenyl 3- [5- (trifluoromethyl) -2 pyridyloxylpropyl ether, represented by the formula (1): CI o o C1

F

3 C N (1) has been known in W096/11909 as an effective ingredient of 15 a pesticide. Further, a pesticidal emulsifiable concentrate comprising pyridalyl as an effective ingredient has also been disclosed in W096/11909.

P')PER\MIC2( 5215927 amndmn doc-13)1/21X)9 -2 However, the pesticidal emulsifiable concentrate comprising pyridalyl as the effective ingredient disclosed in Preparation Example 1 of W096/11909 has not always sufficient emulsion stability depending upon conditions, 5 when it is diluted with water. Then, it is desired to develop a pesticidal emulsifiable concentrate which comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability. In one aspect the invention provides a pesticidal 10 emulsifiable concentrate which comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability upon dilution with water. This and other advantages of the present invention will become apparent to those skilled in the art from the 15 following description. SUMMARY OF THE INVENTION The present inventors have studied intensively to obtain a pesticidal emulsifiable concentrate which 20 comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability upon dilution with water. As a result, they have found that a pesticidal emulsifiable concentrate containing an aromatic hydrocarbon as a solvent, and a polyoxyethylene polyoxypropylene 25 polyarylphenol and an alkylarylsulfonate as surfactants maybe attained. That is, the pesticidal emulsifiable concentrate of the present invention comprises pyridalyl, a 3 polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon. The proportion of the respective ingredients in the pesticidal emulsifiable concentrate of the present 5 invention is usually 5 to 60% by weight of pyridalyl, 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol, 2 to 15% by weight of the alkylarylsulfonate and 10 to 90% by weight of the aromatic hydrocarbon. 10 The pesticidal emulsifiable concentrate of the present invention may essentially consist of pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon. Alternatively, it may further contain other auxiliaries 15 such as other solvents, antioxidants, preservatives, coloring agents, and the like. Examples of the other solvent include esters such as methyl oleate and dibutyl adipate; aliphatic hydrocarbons such as octane and decane; ketones such as cyclohexanone; 20 and amides such as N,N-dimethylformamide and N methylpyrrolidone. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Pyridalyl to be used in the present invention can be 25 produced, for example, by the process disclosed in 4 W096/11909. As described above, usually, the pesticidal emulsifiable concentrate can contain 5 to 60% by weight of pyridalyl. In the present invention, the polyoxyethylene 5 polyoxypropylene polyarylphenol is a nonionic surfactant wherein ethylene oxides and propylene oxides are addition polymerized to the hydroxy moieties of a polymerized phenol compound having two or more aromatic rings, and is also called as a polyoxyethylene polyoxypropylene polyarylphenyl 10 ether. Examples thereof include polyoxyethylene polyoxypropylene polystyrylphenol (or polyoxyethylene polyoxypropylene polystyrylphenyl ether) such as polyoxyethylene polyoxypropylene distyrylphenol and polyoxyethylene polyoxypropylene tristyrylphenol. In the 15 present invention, polyoxyethylene polyoxypropylene tristyrylphenol is preferably used. In the present invention, a commercially available polyoxyethylene polyoxypropylene polyarylphenol as such can be used, and examples the polyoxyethylene polyoxypropylene 20 polyarylphenol include Soprophor .796/P (trade name of polyoxyethylene polyoxypropylene tristyrylphenol manufactured by Rhodia Nicca Co., Ltd.), and Soprophor TSP/461 (trade name of polyoxyethylene polyoxypropylene tristyrylphenol manufactured by Rhodia Nicca Co., Ltd.). 25 Usually, the pesticidal emulsifiable concentrate of the 5 present invention contains 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol. The alkyl group of the alkylarylsulfonate to be used in the present invention usually has 8 to 15 carbon atoms. 5 Further, examples of the salt of the alkylarylsulfonate include alkali metal salts such as sodium salt, potassium salt, etc.; and alkaline earth metal salts such as calcium salt, magnesium salt, etc.; amine salts such as aklylamine salts, alkanol amine salts, cyclohexylamine salt, etc.; and 10 ammonium salt. Examples of the alkylarylsulfonate to be used in the present invention include alkylbenzenesulfonate. As specific examples thereof, there are sodium dodecylbenzenesulfonate and calcium dodecylbenzenesulfonate. 15 The pesticidal emulsifiable concentrate of the present invention usually contains 2 to 15% by weight of the alkylarylsulfonate. Examples of the aromatic hydrocarbon to be used in the present invention include liquid aromatic hydrocarbon 20 solvents such as alkylbenzenes (e.g., toluene, etc.), dialylbenzenes (e.g., xylene, etc.), trialkylbenzenes (e.g., trimethylbenzene, etc.), alkylnaphthalenes (e.g., methylnaphthalene, etc.), dialkylnaphthalenes (e.g., dimethylnephthalene, etc.), trialkylnaphthalenes (e.g., 25 dimethyl-monopropylnaphthalene, etc.), phenylxylylethane, 6 and the like. In the present invention, as the aromatic hydrocarbon, a commercially available solvent as such can be used. Examples commercially available solvents include Hisol SAS 5 296 (trade name of a mixture of 1-phenyl-l-xylylethane and 1-phenyl-1-ethylphenylethane manufactured by Nippon Oil Corporation), Cactus Solvent HP-MN (trade name of methylnaphthalene 80% manufactured by Nikko Petrochemical Company), Cactus Solvent HP-DMN (dimethylnaphthalene 80% 10 manufactured by Nikko Petrochemical Company), Cactus Solvent P-100 (trade name of C 910 alkylbenzene manufactured by Nikko Petrochemical Company), Cactus Solvent P-150 (trade name of alkylbenzene manufactured by Nikko Petrochemical Company), Cactus Solvent P-180 (trade name of 15 a mixture of methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent P-200 (trade name of a mixture of methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent P-220 (trade name of a mixture 20 methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent PAD-1 (dimethyl-monoisopropylnaphthalene manufactured by Nikko Petrochemical Company), Solvesso 100 (trade name of aromatic hydrocarbon manufactured by Exxon Chemical 25 Company), Solvesso 150 (trade name of aromatic hydrocarbon 7 manufactured by Exxon Chemical Company), Solvesso 200 (trade name of aromatic hydrocarbon manufactured by Exxon Chemical Company), Solvesso 150 ND (manufactured by ExxonMobil Chemical Company), Solvesso 200 ND (manufactured 5 by ExxonMobil Chemical Company), ULTRA LOW NAPHTHALENE AROMATIC 150 (manufactured by ExxonMobil Chemical Company), ULTRA LAW NAPHTHALENE AROMATIC 200 (manufactured by ExxonMobil Chemical Company), Swasol 100 (trade name of toluene manufactured by Maruzen Petrochemical Company, 10 Limited) and Swasol 200 (trade name of xylene manufactured by Maruzen Petrochemical Company, Limited). The pesticidal emulsifiable concentrate of the present invention usually contains 10 to 90% by weight of the aromatic hydrocarbon. 15 The pesticidal emulsifiable concentrate of the present invention can be produced, for example, by stirring pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon, if necessary, with heating (80*C of lower) to 20 obtain a uniform mixture and, if necessary, filtering the resultant mixture. The pesticidal emulsifiable concentrate of the present invention is usually applied to pests or pest inhabiting places after water dilution. That is, for example, the 25 pesticidal emulsifiable concentrate is applied by diluting 8 the concentrate about 10 to 5,000 times with water and spraying the diluted solution on pest inhabiting plants and/or soil. Further, the pesticidal emulsifiable concentrate of the present invention can be applied by 5 aerial spraying such as by a helicopter, etc. The application amount of the pesticidal emulsifiable concentrate of the present invention is usually 0.1 to 100 g/10 a in terms of pyridalyl. The present invention will hereinafter be further 10 illustrated by the following production examples, comparative production examples and test example; however, the present invention is not limited to these examples. Production Example 1 Ten parts by weight of pyridalyl, 14.0 parts by weight 15 of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide were mixed at room temperature to 20 obtain the pesticidal emulsifiable concentrate of the present invention (hereinafter referred to as the present invention emulsifiable concentrate 1). Production Example 2 Ten parts by weight of pyridalyl, 14.0 parts by weight 25 of polyoxyethylene polyoxypropylene tristyrylphenol 9 (Soprophor TSP/724 manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide were mixed at room temperature to 5 obtain the pesticidal emulsifiable concentrate of the present invention (hereinafter referred to as the present invention emulsifiable concentrate 2). Production Example 3 Fifty parts by weight of pyridalyl, 9.3 parts by 10 weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 4.0 parts by weight of calcium dodecylbenzenesulfonate, 18.35 parts by weight of xylene and 18.35 parts by weight of N,N-dimethylformamide were mixed at room temperature to 15 obtain the pesticidal emulsifiable concentrate of the present invention. Production Example 4 Fifty parts by weight of pyridalyl, 9.3 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol 20 (Soprophor TSP/724 manufactured by Rhodia Nicca Co., Ltd.), 4.0 parts by weight of calcium dodecylbenzenesulfonate, 18.35 parts by weight of xylene and 18.35 parts by weight of N,N-dimethylformamide were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the 25 present invention.

10 Production Example 5 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 5 6.0 parts by weight of calcium dodecylbenzenesulfonate and 70.0 parts by weight of xylene were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention. Comparative Production Example 1 10 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene tristyrylphenol (Soprophor TS10 manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N 15 dimethylformamide were mixed at room temperature to obtain a pesticidal emulsifiable concentrate (hereinafter referred to as the comparative emulsifiable concentrate 1). Comparative Production Example 2 Ten parts by weight of pyridalyl, 14.0 parts by weight 20 of polyoxyethylene tristyrylphenol (Soprophor BSU manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N dimethylformamide were mixed at room temperature to obtain 25 a pesticidal emulsifiable concentrate (hereinafter referred 11 to as the comparative emulsifiable concentrate 2). The following Test Example illustrates emulsion stability of the pesticidal emulsifiable concentrate of the present invention. 5 Test Example In water, 3.04 g of potassium chloride and 1.39 g of magnesium chloride 6 hydrate were dissolved, and the solution was made up to 100 ml with water to prepare a hard water stock. One ml of the hard water stock was diluted 10 and made up to 1,000 ml with water to prepare a test hard water having the water hardness of 34.2 ppm. Likewise, 14.6 ml of the hard water stock was diluted and made up to 1,000 ml with water to prepare a test hard water having the water hardness of 500 ppm. 15 Ninety five ml of the above test hard water having the water hardness of 34.2 ppm was placed in a 100 ml-measuring cylinder with a stopper and the measuring cylinder was allowed to stand in a constant temperature water bath at 20*C for a while to adjust the water temperature to 200C. 20 Then, 5 ml of the present invention emulsifiable concentrate obtained in the above Production Example was added to the measuring cylinder, and the measuring cylinder was repeatedly turned upside down 30 times at a rate of once per 2 seconds. After that, the measuring cylinder was 25 allowed to stand again in a constant temperature water bath 12 at 200C for 1 hour. When the state of the emulsion in the measuring cylinder was observed after standing, both of the present invention emulsifiable concentrates 1 and 2 maintained uniform emulsion states. When the same test was 5 conducted by using the pesticidal emulsifiable concentrate obtained in the above Comparative Production Example, a small amount of creamy separation was observed in case of using the comparative emulsifiable concentrate 1, and a trace amount of creamy separation was observed in case of 10 using the comparative emulsifiable concentrate 2. When the same test was conducted by using the above test hard water having the water hardness of 500 ppm to observe the state of the emulsion, both of the present invention emulsifiable concentrates 1 and 2 maintained 15 uniform emulsion states. However, 0.5 cc of creamy separation was observed in case of using the comparative emulsifiable concentrate 1, and a small amount of creamy separation was observed in case of using the comparative emulsifiable concentrate 2. 20 As described hereinabove, the pesticidal emulsifiable concentrate of the present invention is excellent in emulsion stability upon water dilution, and is useful as a pesticide.

POPER\MIC\M)S215927 andmntdoc-211)l/2)19 - 13 Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of 5 a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any 10 matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates. 15

Claims (6)

1. A pesticidal emulsifiable concentrate which comprises pyridalyl, a polyoxyethylene polyoxypropylene 5 polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon.

2. A pesticidal emulsifiable concentrate according to claim 1, which comprises 5 to 60% by weight of pyridalyl, 2 10 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol, 2 to 15% by weight of the alkylarylsulfonate and 10 to 90% by weight of the aromatic hydrocarbon. 15

3. A pesticidal emulsifiable concentrate according to claim 1 or 2, wherein the polyoxyethylene polyoxypropylene polyarylphenol is polyoxyethylene polyoxypropylene tristyrylphenol. 20

4. A pesticidal emulsifiable concentrate according to claim 3, wherein the alkylarylsulfonate is a dodecylbenzenesulfonate.

5. A pesticidal emulsifiable concentrate according to 25 claim 3, wherein the alkylarylsulfonate is calcium dodecylbenzenesulfonate.

6. A pesticidal emulsifiable concentrate according to any one of claims 1 to 5 substantially as hereinbefore 30 described.