Title of Invention

A PESTICIDAL COMPOSITION CONTAINING PYRIDARYL

Abstract A pesticidal composition which comprises 5 to 60% by weight of pyridaryl, 2-15% by weight of a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, 2-15% by weight of a salt of alkylbenzenesulfonic acid and 10-90% by weight of an aromatic hydrocarbon.
Full Text

Pesticidal composition
Technical Field The present invention relates to a pesticidal composition containing pyridaryl as an active ingredient.
Background Arts Pyridaryl, which is 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-[5-(trifluoromethyl)-2-pyridyloxy]propyl ether and given by the formula (1) below,

is known as an active ingredient of an insecticidal and acaricidal composition. Further, a pesticidal composition formulated to an emulsifiable concentrate containing pyridaryl as an active ingredient is also known in WO96/11909.
Disclosure of the Invention
The present invention provides a pesticidal composition containing pyridaryl as an active ingredient and having an excellent emulsion stability of its dilution with water.
The pesticidal composition comprises pyridaryl, a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, a salt of alkylbenzenesulfonic acid and an aromatic hydrocarbon. The pesticidal composition is generally a pesticidal emulsifiable concentrate and it has excellent emulsion stability when it is diluted with water.
The content of each component for constituting the pesticidal composition of the invention is usually 5-60% by weight of pyridaryl, 2-15%

by weight of a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, 2-15% by weight of a salt of alkylbenzenesulfonic acid and 10-90% by weight of an aromatic hydrocarbon.
The pesticidal composition of the invention may consist essentially of pyridaryl, a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, a salt of alkylbenzenesulfonic acid and an aromatic hydrocarbon, and further may contain the other auxiliaries for formulation such as the other solvent, antioxidant, preservative and dyestuff unless its content is large enough to antagonize the effect of the invention. Examples of the other solvent include carboxylate esters such as methyl oleate and dibutyl adipate, aliphatic hydrocarbons such as octane and decane, ketones such as cyclohexanone, and amides such as N,N-dimethylformamide and N-methylpyrrolidone.
Pyridaryl used for the invention can be, for example, produced by the method described in WO96/11909. The content of pyridaryl in the pesticidal composition of the invention is usually 5-60% by weight as mentioned above.
The alkoxylated castor oil used for the invention is a compound obtained by addition polymerization of alkylene oxide having 2-4 carbon number (e.g., ethylene oxide, propylene oxide) to castor oil in the presence of a base. The examples include ethoxylated castor oil obtained by addition polymerization of ethylene oxide to castor oil and ethoxylated propoxylated castor oil obtained by addition polymerization of ethylene oxide and propylene oxide to castor oil in random or in block. The alkoxylated hydrogenated castor oil is a compound obtained by addition polymerization of alkylene oxide having 2-4 carbon number (e.g., ethylene oxide, propylene oxide) to hydrogenated castor oil (also called hardened castor oil) in the presence of a base. The examples include ethoxylated hydrogenated castor oil obtained by addition polymerization of ethylene oxide to hydrogenated castor oil and ethoxylated propoxylated hydrogenated castor oil obtained by

addition polymerization of ethylene oxide and propylene oxide to hydrogenated castor oil in random or in block. In the present invention, alkoxylated castor oil is preferably used and ethoxylated castor oil is more preferably used.
Examples of the ethoxylated castor oil on the market include Alkamuls R81 (commercial name of Rhodia Nicca), Alkamuls BR (commercial name of Rhodia Nicca), Alkamuls OR40 (commercial name of Rhodia Nicca), Alkamuls 14R (commercial name of Rhodia Nicca), Sorpol CA30 (commercial name of Toho Chemical Industry), Sorpol CA42 (commercial name of Toho Chemical Industry), CO20TX (commercial name of Nikko Chemicals, number of ethylene oxide addition: 20 mols), CO40TX (commercial name of Nikko Chemicals, number of ethylene oxide addition: 40 mols), CO50TX (commercial name of Nikko Chemicals, number of ethylene oxide addition: 50 mols), CO60TX (commercial name of Nikko Chemicals, number of ethylene oxide addition: 60 mols), Etocas 29 (commercial name of Croda Japan, number of ethylene oxide addition: 29 mols), Etocas 35 (commercial name of Croda Japan, number of ethylene oxide addition: 35 mpls), Etocas 40 (commercial name of Croda Japan, number of ethylene oxide addition: 40 mols), Etocas 15 (commercial name of Croda Japan, number of ethylene oxide addition: 15 mols), EMALEX C-20 (commercial name of Nihon-Emulsion, number of ethylene oxide addition: 20 mols), EMALEX C-30 (commercial name of Nihon-Emulsion, number of ethylene oxide addition: 30 mols) and EMALEX C-40 (commercial name of
Nihon-Emulsion, number of ethylene oxide addition: 40 mols). Examples of the ethoxylated hydrogenated castor oil on the market include Croduret 7 Special (commercial name of Croda Japan), Croduret 40 LD (commercial name of Croda Japan), Croduret 50 Special (commercial name of Croda Japan), Croduret 60 (commercial name of Croda Japan), HCO20 (commercial name of Nikko Chemicals, number of ethylene oxide addition: 20 mols), HCO-30 (commercial name of Nikko Chemicals, number of ethylene oxide addition: 30 mols), HCO40 (commercial name of Nikko Chemicals, number of ethylene oxide addition: 40 mols), EMALEX HC-20

(commercial name of Nihon-Emulsion, number of ethylene oxide addition: 20 mols), Toximul 8240 (commercial name of Stepan, number of ethylene oxide addition: 36 mols), Toximul 8241 (commercial name of Stepan, number of ethylene oxide addition: 30 mols) and Toximul 8242 (commercial name of Stepan, number of ethylene oxide addition: 40 mols).
The content of the nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil is usually 2-15% by weight in the pesticidal composition of the invention.
The alkyl group in the salt of alkylbenzenesulfonic acid used for the invention is usually C8-C15 alkyl group. Further, examples of the salt of alkylbenzenesulfonic acid include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt and ammonium salt.
Examples of the salt of alkylbenzenesulfonic acid used for the invention include dodecylbenzenesulfonates such as sodium dodecylbenzenesulfonate and calcium dodecylbenzenesulfonate.
The salt of alkylbenzenesulfonic acid is well known as an anionic surfactant. Examples of the salt of alkylbenzenesulfonic acid on the market include Rhodacal 60/BE (commercial name of Rhodia Nicca), Rhodacal 70 (commercial name of Rhodia Nicca), Rhodacal 70/B (commercial name of Rhodia Nicca), Witconate P-1220EH (commercial name of Akzo Nobel) and NANSA EVM62/H (commercial name of Huntsman).
The content of the salt of alkylbenzenesulfonic acid is usually 2-15%
by weight in the pesticidal composition of the invention.
The aromatic hydrocarbon is used as a solvent for the pesticidal composition of the invention. Examples of the aromatic hydrocarbon used for the invention include alkylbenzene such as toluene, dialkylbenzene such as xylene, trialkylbenzene such as trimethybenzene, alkylnaphthalene such as methylnaphthalene, dialkylnaphthalene such as dimethylnaphthalene, trialkylnaphthalene such as dimethylmonoisopropylnaphthalene, and phenylxylylethane.

The aromatic hydrocarbon on the market as it is can be used for the invention. Examples of the aromatic hydrocarbon include Nisseki-Hisol SAS-296 (commercial name of Nippon Oil Corp., a mixture of 1-phenyl-1-xylylethane with 1-phenyM-ethylphenylethane), Cactus Solvent HP-MN (commercial name of Japan Energy Corp., methylnaphthalene: 80%), Cactus Solvent HP-DMN (commercial name of Japan Energy Corp., dimethylnaphthalene: 80%), Cactus Solvent P-100 (commercial name of Japan Energy Corp., C9-10 alkylbenzene), Cactus Solvent P-150 (commercial name of Japan Energy Corp., alkylbenzene), Cactus Solvent P-180 (commercial name of Japan Energy Corp., a mixture of methylnaphthalene with dimethylnaphthalene), Cactus Solvent P-200 (commercial name of Japan Energy Corp., a mixture of methylnaphthalene with dimethylnaphthalene), Cactus Solvent P-220 (commercial name of Japan Energy Corp., a mixture of methylnaphthalene with dimethylnaphthalene), Cactus Solvent PAD-1 (commercial name of Japan Energy Corp., dimethylmonoisopropylnaphthalene), Solvesso 100 (commercial name of Exxon Mobil Corp., aromatic hydrocarbon), Solvesso 150 (commercial name of Exxon Mobil Corp., aromatic hydrocarbon), Solvesso 200 (commercial name of Exxon Mobil Corp., aromatic hydrocarbon), ULTRA LOW NAPHTHALENE AROMATIC 150 (ExxonMobil Chemical Company), ULTRA LOW NAPHTHALENE AROMATIC 200 (ExxonMobil Chemical Company), Suwazol 100 (commercial name of Maruzen Petrochemical, xylene), Suwazol 200
(commercial name of Maruzen Petrochemical, xylene), Solvesso 150ND
(commercial name of ExxonMobil Chemical Company, aromatic
hydrocarbon, mainly C101 alkylbenzene) and Solvesso 200ND
(commercial name of ExxonMobil Chemical Company, aromatic
hydrocarbon, mainly Cll-14 alkylnaphthalene)
The content of the aromatic hydrocarbon is usually 10-90% by weight in the pesticidal composition of the invention.
The pesticidal composition of the invention can further contain the other auxiliaries for formulation unless its content is large enough to

antagonize the effect of the invention. Examples of the other additives and solvents
include antioxidants such as 3-/2-t-butyl-4-hydroxyanisol and butylated hydroxytoluene,
nitrile solvents such as acetonitrile and isobutyronitrile, ether solvents such as diisopropyl
ether and dioxane, amide solvents such as N, N-dimethylformamide and
N, N-dimethylactamide, halogenated hydrocarbon solvents such as dichloromethane,
trichloroethane and carbon tetrachloride, and vegetable oils such as soybean oil and
cottonseed oil.
The pesticidal composition of the invention can be produced, for example, by stirring a
nonionic surfactant selected from the group consisting of alkoxylated castor oil and
alkoxylated hydrogenated castor oil, a salt of alkylbenzenesulfonic acid, pyridaryl and an
aromatic hydrocarbon, optionally under heating, for example 80°C or less, to be uniform
and filtering, if necessary.
The pesticidal composition of the invention is usually diluted with water and applied to
pests or a place where the pests inhabit. Namely, the pesticidal emulsifiable concentrate
is diluted with water, for example, about 10-5000 times and applied to crops and/or soil
where the pests inhabit. It is also diluted with water about 10-1000 times and provided
for aerial application by helicopter and the like.
The dilution with water is usually performed at the place the dilution is applied. Through
hard water may cause trouble at that time, the pesticidal composition of the invention can
be diluted with hard water as well as soft water.
The application rate of the pesticidal composition of the invention is usually 0.1 to lOOg
per 1000m2 in the amount of pyridaryl.
This invention is not based on research or information on biological resources obtained from India. This invention was completed in Japan.
Examples
Hereinafter, the present invention is explained by production examples, test example and so on in more detail; however, the present invention is not restricted to these examples. Production example 1

Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated castor oil (Alkamuls R81, produced by Rhodia Nicca), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 35.0 parts by weight of xylene and 35.0 parts by weight of N,N- dime thy lformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC l). Production example 2
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated castor oil (Alkamuls BR, produced by Rhodia Nicca), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 2). Production example 3
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated castor oil (Alkamuls OR40, produced by Rhodia Nicca), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 3). Production example 4
Ten (10.0) parts by weight of pyridaryl, 20.0 parts by weight of a mixture of alkoxylated castor oil and calcium dodecylbenzenesulfonate
(Sorpol 4322, produced by Toho Chemical), 35.0 parts by weight of xylene
and 35.0 parts by weight of N,N-dimethylformamide were mixed at room
temperature to give a pesticidal composition (hereinafter, referred to EC 4).
Production example 5
Fifty (50.0) parts by weight of pyridaryl, 9.3 parts by weight of
alkoxylated castor oil (Toximul 8241, produced by Stepan), 4.0 parts by
weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by
Rhodia Nicca), 18.35 parts by weight of xylene and 18.35 parts by weight of

N,N-dimethylformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 5). Production example 6
Fifty (50.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated castor oil (Toximul 8241, produced by Stepan), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 15.0 parts by weight of xylene and 15.0 parts by weight of N,N-dime thy lformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 6). Production example 7
Ten (10.0) parts by weight of pyridaryl, 9.3 parts by weight of alkoxylated castor oil (Alkamuls OR40, produced by Rhodia Nicca), 4.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 38.35 parts by weight of xylene and 38.35 parts by weight of N,N-dimethylformamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 7). Production example 8
Ten (10.0) parts by weight of pyridaryl, 20.0 parts by weight of a mixture of alkoxylated castor oil and calcium dodecylbenzenesulfonate (Sorpol 4322, produced by Toho Chemical) and 70.0 parts by weight of Solvesso 150 (aromatic hydrocarbon, produced by Exxon Mobil Corp.) were mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 8).
Production example 9
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of
alkoxylated castor oil (Toximul 8241, produced by Stepan), 6.0 parts by
weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by
Rhodia Nicca) and 70.0 parts by weight of Solvesso 200 (aromatic
hydrocarbon, produced by Exxon Mobil Corp.) were mixed at room
temperature to give a pesticidal composition (hereinafter, referred to EC 9).
Production example 10

Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated hydrogenated castor oil (HCO-0, produced by Nikko Chemicals), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca), 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide are mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 10). Production example 11
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of alkoxylated hydrogenated castor oil (HCO40, produced by Nikko Chemicals), 6.0 parts by weight of calcium dodecylbenzenesulfonate (Rhodacal 60/BE, produced by Rhodia Nicca) and 70.0 parts by weight of Solvesso 200 (aromatic hydrocarbon, produced by Exxon Mobil Corp.) are mixed at room temperature to give a pesticidal composition (hereinafter, referred to EC 11). Reference production example 1
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of polyoxyethylene tristyrylphenol (Soprophor TS10, produced by Rhodia Nicca), 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 give a pesticidal composition (hereinafter, referred to Reference EC 1).
Reference production example 2
Ten (10.0) parts by weight of pyridaryl, 14.0 parts by weight of polyoxyethylene tristyrylphenol (Soprophor BSU, produced by Rhodia Nicca), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylforrnamide were mixed at room temperature to give a pesticidal composition (hereinafter, referred to Reference EC 2).
The emulsion stability of the pesticidal composition of the invention is demonstrated by the following test example. Test example

In water 3.04g of calcium chloride and 1.39g of magnesium chloride hexahydrate were dissolved, and the solution was made up to 100ml with water to prepare a hard water stock. One milliliter of the hard water stock was diluted and made up to 1000ml with water to prepare a test hard water having the water hardness of 34.2ppm.
In a 100-ml graduated cylinder with a stopper 95ml of the above test hard water having the water hardness of 34.2ppm was placed and the graduated cylinder was allowed to stand in a constant temperature water bath at 20°C for a while to adjust the water temperature to 20°C. Then, 5ml of the pesticidal composition of the invention obtained in the above production examples was added to the graduated cylinder, and the graduated cylinder was repeatedly turned upside down 10 times at a rate of once per two seconds. After that, the graduated cylinder was allowed to stand again in the constant temperature water bath at 20°C for one hour. When the state of the emulsion in the graduated cylinder was observed after standing, ECl to EC9 maintained uniform emulsion states and were observed neither creamy separation nor oily separation.
When the same test was conducted by using the Reference ECs, which are disclosed in Formulation Example 1 of WO96/11909 and obtained in the above reference production examples, a small amount of creamy separation and oily separation was observed in case of using Reference ECl and a slight amount of creamy separation was observed in
case of using Reference EC2.
Industrial Applicability The pesticidal composition of the invention is useful for a pesticide for controlling insects and acarina.

WE CLAIM:
1. A pesticidal composition which comprises 5 to 60% by weight of pyridaryl, 2-15% by weight of a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, 2-15% by weight of a salt of alkylbenzenesulfonic acid and 10-90% by weight of an aromatic hydrocarbon.
2. The pesticidal composition as claimed in claim 1, wherein the nonionic surfactant is an alkoxylated castor oil.
3. The pesticidal composition as claimed in claim 1, wherein the salt of alkylbenzenesulfonic acid is a salt of dodecylbenzenesulfonic acid.
4. The pesticidal composition as claimed in claim 1, wherein the salt of alkylbenzenesulfonic acid is calcium dodecylbenzenesulfonate.



ABSTRACT

Title: A pesticidal composition containing pyridaryl
A pesticidal composition which comprises 5 to 60% by weight of pyridaryl, 2-15% by weight of a nonionic surfactant selected from the group consisting of alkoxylated castor oil and alkoxylated hydrogenated castor oil, 2-15% by weight of a salt of alkylbenzenesulfonic acid and 10-90% by weight of an aromatic hydrocarbon.

Documents:

01099-kol-2006-correspondence-1.1.pdf

01099-kol-2006.abstract.pdf

01099-kol-2006.claims.pdf

01099-kol-2006.correspondence others.pdf

01099-kol-2006.descripotion(complete).pdf

01099-kol-2006.form-1.pdf

01099-kol-2006.form-2.pdf

01099-kol-2006.form-3.pdf

01099-kol-2006.form-5.pdf

01099-kol-2006.priority document.pdf

1099-KOL-2006-(26-04-2013)-CORRESPONDENCE.pdf

1099-KOL-2006-(26-04-2013)-PA.pdf

1099-KOL-2006-(29-04-2013)-ABSTRACT.pdf

1099-KOL-2006-(29-04-2013)-CLAIMS.pdf

1099-KOL-2006-(29-04-2013)-CORRESPONDENCE.pdf

1099-KOL-2006-(29-04-2013)-DESCRIPTION (COMPLETE).pdf

1099-KOL-2006-(29-04-2013)-FORM 1.pdf

1099-KOL-2006-(29-04-2013)-FORM 2.pdf

1099-KOL-2006-(29-04-2013)-FORM 3.pdf

1099-KOL-2006-(29-04-2013)-OTHERS.pdf

1099-KOL-2006-CANCELLED PAGES.pdf

1099-KOL-2006-CORRESPONDENCE-1.1.pdf

1099-KOL-2006-CORRESPONDENCE.pdf

1099-KOL-2006-EXAMINATION REPORT.pdf

1099-kol-2006-form 18.pdf

1099-KOL-2006-FORM 26.pdf

1099-KOL-2006-GRANTED-ABSTRACT.pdf

1099-KOL-2006-GRANTED-CLAIMS.pdf

1099-KOL-2006-GRANTED-DESCRIPTION (COMPLETE).pdf

1099-KOL-2006-GRANTED-FORM 1.pdf

1099-KOL-2006-GRANTED-FORM 2.pdf

1099-KOL-2006-GRANTED-FORM 3.pdf

1099-KOL-2006-GRANTED-FORM 5.pdf

1099-KOL-2006-GRANTED-SPECIFICATION-COMPLETE.pdf

1099-KOL-2006-OTHERS.pdf

1099-KOL-2006-PRIORITY DOCUMENT.pdf

1099-KOL-2006-REPLY TO EXAMINATION REPORT.pdf

1099-KOL-2006-TRANSLATED COPY OF PRIORITY DOCUMENT.pdf


Patent Number 257702
Indian Patent Application Number 1099/KOL/2006
PG Journal Number 44/2013
Publication Date 01-Nov-2013
Grant Date 29-Oct-2013
Date of Filing 19-Oct-2006
Name of Patentee SUMITOMO CHEMICAL COMPANY,LIMITED
Applicant Address 27-1,Shinkawa 2-chome,Chou-ku, Tpkyo 104-8260
Inventors:
# Inventor's Name Inventor's Address
1 YUMIKO KOZUKI 2-9-9, Kiyoshikojin,Takarazuka-shi, Hyogo
2 YASUSHI MIMA 2-10-4-422 sonehigashino-cho, Toyonaka-shi,Osaka
PCT International Classification Number A01P13/00; A01N25/04; A01N25/30;
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2005-315886 2005-10-31 Japan