NL1042280B1 - Liquid agrochemical - Google Patents

Liquid agrochemical Download PDF

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Publication number
NL1042280B1
NL1042280B1 NL1042280A NL1042280A NL1042280B1 NL 1042280 B1 NL1042280 B1 NL 1042280B1 NL 1042280 A NL1042280 A NL 1042280A NL 1042280 A NL1042280 A NL 1042280A NL 1042280 B1 NL1042280 B1 NL 1042280B1
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weight
manufactured
benzyl alcohol
present
liquid agrochemical
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NL1042280A
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Dutch (nl)
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NL1042280A (en
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Watanabe Atsushi
Abe Toru
Kawanaka Hideo
Teramoto Takeshi
Nakagawa Kota
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Sumitomo Chemical Co
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/12—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Management, Administration, Business Operations System, And Electronic Commerce (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

The present invention provides a liquid agrochemical comprising a pyridazine compound of the formula (I): wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom, a surfactant(s), and benzyl alcohol and an aromatic hydrocarbon(s) at a given content and content ratio thereof, which has an excellent property.

Description

LIQUID AGROCHEMICAL
TECHNICAL FIELD
[0001]
This application claims priority to and benefit of Japanese Patent Application Serial No. 2016-041875 filed on March 4,2016, the entire contents of which are incorporated by reference.
The present invention relates to a liquid agrochemical.
BACKGROUND ART
[0002]
Hereto, it has been known (see Patent Documents 1 and 2) as an active compound for controlling plant diseases a pyridazine compound of the formula (I):
(I) wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom.
CITATION LIST PATENT DOCUMENT
[0003]
Patent Document 1: WO 2005/121104 Patent Document 2: WO 2006/001175 SUMMARY OF THE INVENTION (PROBLEMS TO BE SOLVED BY INVENTION) [0004]
The object of the present invention is to provide a liquid agrochemical comprising the above-mentioned pyridazine compound and having an excellent property. (MEANS TO SOLVE PROBLEMS) [0005]
The inventors have intensively studied to find out a liquid agrochemical comprising the above-mentioned pyridazine compound and having an excellent property, and as a result, found out that a liquid agrochemical comprising the above-mentioned pyridazine compound, a surfactant(s), benzyl alcohol and an aromatic hydrocarbon(s) has an excellent property.
That is, the present invention provides the followings [1] to [8].
[1] A liquid agrochemical comprising 1 to 11% by weight of a pyridazine compound of formula (I):
(I) wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom, 1 to 30% by weight of a surfactant(s), benzyl alcohol and an aromatic hydrocarbon(s), wherein the total content of benzyl alcohol and the aromatic hydrocarbon(s) is within the range of 50 to 98% by weight and the weight ratio of benzyl alcohol to the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is within the range of 30:70 to 85:15.
[2] The liquid agrochemical as described in [1] wherein the weight ratio of benzyl alcohol to the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) is within the range of 30:70 to 80:20.
[3] The liquid agrochemical as described in [1] or [2] wherein the aromatic hydrocarbon(s) is at least one alkylbenzene or at least one alkylnaphthalene.
[4] The liquid agrochemical as described in any one of [1] to [3] wherein the content of pyridazine compound is within the range of 4 to 10% by weight.
[5] The liquid agrochemical as described in any one of [1] to [3] wherein the content of pyridazine compound is within the range of 4 to 8% by weight.
[6] The liquid agrochemical as described in any one of [ 1 ] to [5] wherein the surfactant comprises a combination of a nonionic surfactant(s) and an anionic surfactant(s).
[7] The liquid agrochemical as described in any one of [ 1] to [5] wherein the surfactant(s) comprises dodecylbenzene sulfonate in combination with polyoxyalkylene polyaryl ether or polyoxyalkylene alkyl ether.
[8] The liquid agrochemical as described in any one of [ 1] to [7] which is an emulsifiable concentrate.
[0006]
The present invention can provide a liquid agrochemical comprising the above-mentioned pyridazine compound and also having excellent property in terms of emulsion stability and storage stability at low temperature.
MODE FOR CARRYING OUT THE INVENTION
[0007]
The liquid agrochemical of the present invention (herein after referred to as "present agrochemical") comprises a pyridazine compound of formula (I):
(I) wherein R1 is chloro atom, bromo atom, cyano group or methyl group; and R2 is hydrogen atom or fluoro atom (hereinafter referred to as "present pyridazine compound").
[0008]
The present pyridazine compound of formula (I) wherein R1 is chloro atom or bromo atom may be prepared according to a method known in the art, as disclosed in WO 2005/121104, which hereby is incorporated by reference.
The present pyridazine compound of formula (I) wherein R1 is methyl group may be prepared according to a method known in the art, as disclosed in WO 2006/001175, which hereby is incorporated by reference.
The present pyridazine compound of formula (I) wherein R1 is cyano group may be prepared according to a method known in the art, as disclosed in WO 2014/013841, which hereby is incorporated by reference.
[0009]
Examples of the present pyridazine compound include:
The compound of formula (I) wherein R1 is chloro atom and R2 is hydrogen atom;
The compound of formula (I) wherein R1 is bromo atom and R2 is hydrogen atom;
The compound of formula (I) wherein R' is cyano group and R2 is hydrogen atom;
The compound of formula (1) wherein R' is methyl group and R2 is hydrogen atom;
The compound of formula (I) wherein R1 is chloro atom and R2 is fluoro atom;
The compound of formula (I) wherein R1 is bromo atom and R2 is fluoro atom;
The compound of formula (I) wherein R1 is cyano group and R2 is fluoro atom; and The compound of formula (I) wherein R1 is methyl group and R2 is fluoro atom.
[0010]
The present agrochemical comprises 1 to 11% by weight, preferably 4 to 10% by weight, or more preferably 4 to 8% by weight of the present pyridazine compound.
[0011]
The present agrochemical comprises benzyl alcohol. Any commercially available benzyl alcohol may be used.
[0012]
The present agrochemical comprises an aromatic hydrocarbon(s). Examples of the aromatic hydrocarbon(s) include alkylbenzenes such as monoalkylbenzenes, dialkylbenzenes and trialkylbenzenes; alkylnaphthalenes such as monoalkylnaphthalene, dialkylnaphthalene, trialkylnaphthalene; phenylxylylethane; and 1-phenyl-1-ethylphenylethane; and mixtures thereof.
Examples of alkylbenzene include toluene, xylene, trimethylbenzene, ethylbenzene, methylethylbenzene, methylpropylbenzene, dimethylethylbenzene, and octadecylbenzene. Specific examples of alkylnaphthalene include methylnaphthalene, dimethylnaphthalene, dodecylnaphthalene, and tridecylnaphthalene.
[0013]
In the present agrochemical, any commercially available aromatic hydrocarbon solvent may be used as the aromatic hydrocarbon(s). Examples of such commercially available aromatic hydrocarbon solvent include Nisseki Hisol SAS-296 (a mixture of 1-phenyl-l-xylylethane and 1-phenyl-1-ethylphenylethane, manufactured by JX Nippon Oil & Energy Corporation), Solvesso 100 (mainly composed of as aromatic hydrocarbons, C9-C10 dialkyl and trialkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.), Solvesso 150 (mainly composed of, as aromatic hydrocarbons, C10-C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.), Solvesso 150ND (mainly composed of, as aromatic hydrocarbons, C10-C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.), Solvesso 200 (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.), Ipsol 100 (mainly composed of C9 aromatic hydrocarbons, manufactured by Idemitsu Kosan Co., Ltd.), Ipsol 150 (mainly composed of CIO aromatic hydrocarbons, manufactured by Idemitsu Kosan Co., Ltd.), T-SOL 150 FLUID (manufactured by TonenGeneral Sekiyu K.K.), SELLSOL A 100 (mainly composed of C9-C10 aromatic hydrocarbons, manufactured by Shell Chemicals), SELLSOL A150 (mainly composed of C9-C11 aromatic hydrocarbons, manufactured by Shell Chemicals) and the others.
[0014]
The weight ratio of benzyl alcohol and the aromatic hydrocarbon(s) (benzyl alcohol: aromatic hydrocarbon(s)) in the present agrochemical is within the range of 30:70 to 85:15, preferably 30:70 to 80:20, and more preferably 30:70 to 70:30.
[0015]
The total content of benzyl alcohol and the aromatic hydrocarbon(s) in the present agrochemical is 50 to 98% by weight, and preferably 70 to 98% by weight, and more preferably 70 to 95% by weight.
[0016]
The present agrochemical comprises a surfactant(s). Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants and amphoteric surfactants.
[0017]
Examples of the nonionic surfactant include polyoxyethylene-polyoxypropylene block copolymers; polyoxyalkylene fatty acid esters such as polyoxyethylene fatty acid esters and polyoxyethylene polyoxypropylene fatty acid esters; polyoxyalkylene polyaryl ethers such as polyoxyethylene tristyrylphenyl ethers, polyoxyethylene polyaryl ethers, and polyoxyethylene polyoxypropylene polyaryl ethers; polyoxyalkylene alkylaryl ethers such as polyoxyethylene alkylaryl ethers, and polyoxyethylene polyoxypropylene alkylaryl ethers; polyoxyalkylene alkyl ethers such as polyoxyethylene alkyl ethers, and polyoxyethylene polyoxypropylene alkyl ethers; polyoxyalkylene vegetable oils such as polyoxyethylene castor oil and polyoxyethylene polyoxypropylene castor oil; polyoxyalkylene hydrogenated vegetable oils such as polyoxyethylene hydrogenated castor oil; glycerin fatty acid esters; sorbitan fatty acid esters such as sorbitan laurate, sorbitan stearate, sorbitan oleate, and sorbitan trioleate; and polyoxyalkylene sorbitan fatty acid esters such as polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, and polyoxyethylene sorbitan trioleate. Among the above-mentioned nonionic surfactants, one or more nonionic surfactant selected from the group consisting of polyoxyalkylene polyaryl ethers and polyoxyalkylene alkyl ethers is preferably used.
[0018]
Examples of the anionic surfactant include alkylarylsulfonates such as dodecylbenzene sulfonate; dialkyl sulfosuccinates such as di-(2-ethylhexyl)sulfosuccinate; polyoxyalkylene polyaryl ether sulfate ester salts such as polyoxyethylene distyiylphenyl ether sulfate ester salts; polyoxyalkylene polyaryl ether phosphate ester salts such as polyoxyethylene tristyryl phenyl ether phosphate ester salts; polyoxyalkylene alkylaryl ether phosphate ester salts such as polyoxyethylene alkylaryl ether phosphate ester salts; polyoxyalkylene alkyl ether phosphate ester salts such as polyoxyethylene alkyl ether phosphate ester salts. Examples of such sulfonate, sulfate ester salts and phosphate ester salts include sodium salt, potassium salt, calcium salt and ammonium salt. Among the above-mentioned anionic surfactants, dodecylbenzene sulfonate is preferably used.
[0019]
Examples of the cationic surfactant include alkylamine hydrochlorides such as dodecylamine hydrochloride; alkyl quaternary ammonium salts such as dodecyltrimethyl ammonium salt, alkyldimethylbenzyl ammonium salt, alkylpyridinium salt, alkylisoquinolinium salt, and dialkylmorpholinium salt; benzethonium chloride; and polyalkyl vinyl pyridinium salt.
[0020]
Examples of the amphoteric surfactant include N-laurylalanine, Ν,Ν,Ν-trimethylaminopropionic acid, Ν,Ν,Ν-trihydroxyethylaminopropionic acid, N-hexyl-N,N-dimethylamino acetic acid, l-(2-carboxyethyl) pyrimidinium betaine, and lecithin.
[0021]
In the present agrochemical, one or more of these surfactants are used, and the total content thereof is within the range of 1 to 30% by weight, preferably 1 to 20% by weight, more preferably 1 to 15% by weight, and still more preferably 1 to 10% by weight.
[0022]
The present agrochemical may further comprise another active ingredient(s) for controlling plant diseases, in combination with the present pyridazine compound.
[0023]
The present agrochemical may further comprise an auxiliary agent(s) for formulation, such as a defoaming agent. When the present agrochemical comprises the auxiliary agent(s) for formulation, the total content of such auxiliary agent(s) is within the range of0.0001 to 30% by weight.
[0024] A method of applying the present agrochemical is not limited to specific ones. Although the present agrochemical as itself can be applied as a plant diseases control agent, it also can be applied as an emulsifiable concentrate according to a commonly used method in agrochemical art, for example, applying its diluted liquid with water for controlling plant diseases.
The present agrochemical exists in the liquid state at 25°C.
EXAMPLES
[0025]
The present invention is described in more detail below by way of Examples including Preparation Examples and Test Examples and the like, but the present invention is not limited only to these Examples.
In the following Examples, the above-mentioned pyridazine compound of formula (I) wherein R1 is chloro atom and R2 is hydrogen atom is referred to as "present pyridazine compound (1)".
[0026]
First, Preparation Examples for the present agrochemical are described.
[0027]
Preparation Examples 1 to 4
The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 1, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0028]
Table 1
[0029]
Preparation Examples 5 to 8
The present pyridazine compound (1), Agnique AMD 810 (a mixture ofN,N-dimethyloctane amide and Ν,Ν-dimethyldecanamide, manufactured by BASF), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 2, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0030]
Table 2
[0031]
Preparation Examples 9 to 12
The present pyridazine compound (1), Rhodasurf 860/P (polyoxyethylene alkyl ether, manufactured by Solvay Nicca, Ltd.), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 3, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0032]
Table 3
[0033]
Preparation Examples 13 to 16
The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 150ND (mainly composed of, as aromatic hydrocarbons, C10-C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 4, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0034]
Table 4
[0035]
Preparation Examples 17 to 20
The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS 290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), and benzyl alcohol and xylene were mixed at each weight ratio shown in Table 5, and the mixture was stirred until a homogeneous solution was formed to obtain each of the present agrochemicals.
[0036]
Table 5
[0037]
Preparation Example 21
Eight (8) parts by weight of the present pyridazine compound (1), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 69.7 parts by weight of benzyl alcohol and 12.3 parts by weight of Solvesso 200ND (mainly composed ofi, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0038]
Preparation Example 22
Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts by weight of PURASOLV ML (methyl L-lactate, manufactured by Corbion purac), 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0039]
Preparation Example 23
Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts by weight of Sulfadone LP 100 (N-octyl-2-pyrrolidone, manufactured by ASHLAND), 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0040]
Preparation Example 24
Eight (8) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 20 parts by weight of diethyl oxalate, 27 parts by weight of benzyl alcohol and 25 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0041]
Preparation Example 25
Ten (10) parts by weight of the present pyridazine compound (1), 10 parts by weight of ATPLUS 245 (polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 10 parts by weight of N,N'-dimethylpropyleneurea, 30 parts by weight of benzyl alcohol and 30 parts by weight of Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed to obtain the present agrochemical.
[0042]
Next, Reference Preparation Examples are described.
[0043]
Reference Preparation Examples 1 to 3
The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 6, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0044]
Table 6
[0045]
Reference Preparation Examples 4 to 6
The present pyridazine compound (1), Agnique AMD 810 (a mixture ofN,N-dimethyloctane amide and Ν,Ν-dimethyldecanamide, manufactured by BASF), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 7, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0046]
Table 7
[0047]
Reference Preparation Examples 7 and 8
The present pyridazine compound (1), Rhodasurf 860/P (polyoxyethylene alkyl ether, manufactured by Solvay Nicca, Ltd.), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 200ND (mainly composed of, as aromatic hydrocarbons, C10-C13 alkylnaphthalene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 8, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0048]
Table 8
[0049]
Reference Preparation Examples 9 and 10
The present pyridazine compound (1), Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), benzyl alcohol and Solvesso 150ND (mainly composed of, as aromatic hydrocarbons, C10-C11 alkylbenzene, manufactured by ExxonMobil Chemical Company, Inc.) were mixed at each weight ratio shown in Table 9, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals.
[0050]
Table 9
[0051]
Reference Preparation Example 11
Eight (8) parts by weight of the present pyridazine compound (1), 3 parts by weight of Phenylsulfonat Cal (calcium dodecylbenzenesulfonate, manufactured by Clariant), 7 parts by weight of Emulsogen TS290 (polyoxyethylene tristyrylphenyl ether, manufactured by Clariant), 82 parts by weight of xylene were mixed, and the mixture was stirred until a homogeneous solution was formed to obtain a liquid agrochemical.
[0052]
Further, Test Example is described.
[0053]
Test Example 1
Twenty (20) ml of each of the liquid agrochemicals obtained in the Preparation Examples 1 to 25 and the Reference Preparation Examples 1 to 11 was put into a glass tube, and kept at 0°C. Each of the liquid agrochemicals was kept for 7 days, followed by checking whether there is any crystal precipitation in each of the liquid agrochemicals.
In the result, no crystal precipitation was found in the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 3, 6 and 8. On the other hand, the crystal precipitation was found in the liquid agrochemicals obtained in Reference Preparation Examples 1, 2, 4,5,7, 9, 10 and 11.
[0054]
Test Example 2
The following test was conducted using the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 1 to 11.
Ninety nine (99) ml of CIPAC standard water D (hardness: 342 ppm) at 30°C was put in a 100 ml measuring cylinder with a stopper. One (1) ml of the testing liquid agrochemical was dropped slowly from a height of approximately 8 cm above the surface of the water, and the measuring cylinder was then stoppered. The measuring cylinder was inverted by 180 degrees in 1 second and then returned into its original position in 1 second. After repeating this operation 10 times, the measuring cylinder was allowed to stand in a thermostat chamber at 30°C for 2 hours. Thereafter, state of the liquid in the measuring cylinder was visually observed to evaluate the emulsion stability.
In the result, the liquid containing each of the present agrochemicals obtained in Preparation Examples 1 to 25 and the liquid agrochemicals obtained in Reference Preparation Examples 1,2,4, 5, 7,9, 10 and 11 were kept in a homogeneous emulsified state. On the other hand, the crystal precipitation was found on the bottom face of the cylinder in the liquid containing each of the liquid agrochemicals obtained in Reference Preparation Examples 3, 6 and 8.

Claims (8)

1. Vloeibare agrochemische verbinding met inbegrip van 1 tot 11 % per gewicht van een pyridazine met de formule (I):A liquid agrochemical compound including 1 to 11% by weight of a pyridazine of the formula (I): (I) waarbij R1 staat voor een chloor atoom, een broom atoom, een cyaan groep of een methyl groep; en R2 staat voor een waterstof atoom of een fluor atoom, 1 tot 30 % per gewicht van een oppervlakte actieve stof(fen), en benzylalcohol en een aromatische koolwaterstoffen), waarbij het totale gehalte aan benzylalcohol en de aromatische koolwaterstoffen) in het traject is van 50 tot 98 % per gewicht en de gewichtsverhouding van benzylalcohol tot de aromatische koolwaterstoffen) (benzylalcohol: aromatische koolwaterstoffen)) in het traject is van 30:70 tot 85:15.(I) wherein R 1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group; and R2 represents a hydrogen atom or a fluorine atom, 1 to 30% by weight of a surfactant (s), and benzyl alcohol and an aromatic hydrocarbon), the total content of benzyl alcohol and aromatic hydrocarbons being in the range from 50 to 98% by weight and the weight ratio of benzyl alcohol to aromatic hydrocarbons) (benzyl alcohol: aromatic hydrocarbons)) is in the range of 30:70 to 85:15. 2. De vloeibare agrochemische verbinding, zoals uiteen wordt gezet in conclusie 1, waarbij de gewichtsverhouding van benzylalcohol tot de aromatische koolwaterstoffen) (benzylalcohol: aromatische koolwaterstof) in het traject is van 30:70 tot 80:20.The liquid agrochemical compound as set forth in claim 1, wherein the weight ratio of benzyl alcohol to the aromatic hydrocarbons (benzyl alcohol: aromatic hydrocarbon) is in the range of 30:70 to 80:20. 3. De vloeibare agrochemische verbinding, zoals uiteen wordt gezet in conclusie 1 of 2, waarbij de aromatische koolwaterstoffen) uit ten minste een alkylbenzeen of ten minste een alkylnaftaleen bestaat.The liquid agrochemical compound as set forth in claim 1 or 2, wherein the aromatic hydrocarbons consists of at least one alkyl benzene or at least one alkyl naphthalene. 4. De vloeibare agrochemische verbinding, volgens om het even welke van de conclusies 1 tot en met 3, waarbij het gehalte van de pyridazine verbinding in het traject is van 4 tot 10 % per gewicht.The liquid agrochemical compound according to any of claims 1 to 3, wherein the content of the pyridazine compound is in the range of 4 to 10% by weight. 5. De vloeibare agrochemische verbinding, volgens om het even welke van de conclusies 1 tot en met 3, waarbij het gehalte van de pyridazine verbinding in het traject is van 4 tot 8 % per gewicht.The liquid agrochemical compound according to any of claims 1 to 3, wherein the content of the pyridazine compound is in the range of 4 to 8% by weight. 6. De vloeibare agrochemische verbinding, volgens om het even welke van de conclusies 1 tot en met 5, waarbij de oppervlakte actieve stof een combinatie is van een niet ionogene oppervlakte actieve stof(fen) en een anionogene oppervlakte actieve stof(fen).The liquid agrochemical compound according to any of claims 1 to 5, wherein the surfactant is a combination of a nonionic surfactant (s) and an anionic surfactant (s). 7. De vloeibare agrochemische verbinding, volgens om het even welke van de conclusies 1 tot en met 5, waarbij de oppervlakte actieve stof(fen) met inbegrip is van dodecylbenzeensulfonaat in combinatie met polyoxyalkyleen polyaryl ether of polyoxyalkyleen alkylether.The liquid agrochemical compound according to any of claims 1 to 5, wherein the surfactant (s) is including dodecyl benzene sulfonate in combination with polyoxyalkylene polyaryl ether or polyoxyalkylene alkyl ether. 8. De vloeibare agrochemische verbinding, volgens om het even welke van de conclusies 1 tot en met 7, die uit een emulgeerbaar concentraat bestaat.The liquid agrochemical compound according to any of claims 1 to 7, which consists of an emulsifiable concentrate.
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