DK179289B1 - Liquid agrochemical - Google Patents

Liquid agrochemical Download PDF

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Publication number
DK179289B1
DK179289B1 DKPA201770156A DKPA201770156A DK179289B1 DK 179289 B1 DK179289 B1 DK 179289B1 DK PA201770156 A DKPA201770156 A DK PA201770156A DK PA201770156 A DKPA201770156 A DK PA201770156A DK 179289 B1 DK179289 B1 DK 179289B1
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document
weight
benzyl alcohol
manufactured
agrochemical
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DKPA201770156A
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Danish (da)
Inventor
Atsushi Watanabe
Toru Abe
Hideo Kawanaka
Takeshi Teramoto
Kota Nakagawa
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Sumitomo Chemical Co
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    • 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
    • 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
    • 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
    • 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
    • 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

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

DESCRIPTION
LIQUID AGROCHEMICAL
TECHNICAL FIELD [0001]
The present invention relates to a liquid aqrochemical.
BACKGROUND ART [0002]
Patent documents 1 and 2 describe an active pyridazine compound for controllinq plant disease of the formula (I):
Figure DK179289B1_D0001
wherein
R1 is chloro atom, bromo atom, cyano qroup or methyl qroup; and
R2 is hydroqen atom or fluoro atom.
CITATION LIST
PATENT DOCUMENT
Patent Document 1: WO 2005/121104
Patent Document 2: WO 2006/001175 [0003]
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 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 abovementioned pyridazine compound, one or more surfactant(s), benzyl alcohol and one or more aromatic hydrocarbon (s) has an excellent property.
That is, the present invention provides the following:
[1] A liquid agrochemical comprising to 11% by weight of a pyridazine compound of formula (I):
Figure DK179289B1_D0002
R1 N wherein
R1 is chloro atom, bromo atom, cyano group or methyl group; and
R2 is hydrogen atom or fluoro atom, to 30% by weight of one or more surfactant(s), benzyl alcohol and one or more 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 one or more 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 one or more aromatic hydrocarbon (s) consist of 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 the 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 the 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 one or more nonionic surfactant (s) and one or more 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 provides a liquid agrochemical comprising the above-mentioned pyridazine compound and also having excellent properties 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):
Figure DK179289B1_D0003
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.
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.
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.
[0009]
Examples of the present pyridazine compound include:
The compound of formula (I) wherein R1 is chloro atom and R2
is hydrogen . atom r
The compound of formula (I) wherein R1 is bromo atom and R2
is hydrogen . atom r
The compound of formula (I) wherein R1 is cyano group and R2
is hydrogen atom;
The compound of formula (I) wherein R1 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 one or more 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-lethylphenylethane; 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-lethylphenylethane, 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), and SELLSOL® A150 (mainly composed of C9-C11 aromatic hydrocarbons, manufactured by Shell Chemicals).
[0014]
The weight ratio of benzyl alcohol and 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 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 one or more surfactant(s). Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants and amphoteric surfactants.
[0017]
Examples of nonionic surfactants 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 abovementioned nonionic surfactants, nonionic surfactants selected from the group consisting of polyoxyalkylene polyaryl ethers and polyoxyalkylene alkyl ethers are preferred.
[0018]
Examples of anionic surfactants include alkylarylsulfonates such as dodecylbenzene sulfonate;
dialkyl sulfosuccinates such as di-(2ethylhexyl) sulfosuccinate; polyoxyalkylene polyaryl ether sulfate ester salts such as polyoxyethylene distyrylphenyl 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 preferred.
[0019]
Examples of cationic surfactants 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 amphoteric surfactants include Nlaurylalanine, N,N,N-trimethylaminopropionic acid, Ν,Ν,ΝDK 179289 B1 trihydroxyethylaminopropionic acid, N-hexyl-N,Ndimethylamino acetic acid, 1-(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 one or more additional active ingredient(s) for controlling plant diseases, in combination with the present pyridazine compound.
[0023]
The present agrochemical may further comprise one or more auxiliary agent(s) for formulation, such as a defoaming agent. When the present agrochemical comprises one or more auxiliary agent (s) for formulation, the total content of such auxiliary agent(s) is within the range of 0.0001 to 30% by weight.
[0024]
The methods of applying the present agrochemical are not limited to specific ones. Although the present agrochemical as itself can be applied as a plant diseases control agent, it can also be applied as an emulsifiable concentrate according to a commonly used method in agrochemical art, for example, by applying it diluted 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 but the present invention is not limited 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 the weight ratios 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
Preparation Example No. 1 2 3 4
Present pyridazine compound (1) 10 10 10 10
Phenylsulfonat Cal® 3 3 3 3
Emulsogen® TS290 7 7 7 7
Benzyl alcohol 24 40 56 64
Solvesso® 200ND 56 40 24 16
Benzyl alcohol: Solvesso® 200ND (weight ratio) 30:70 50 :50 70:30 80:20
[0029]
Preparation Examples 5 to 8
The present pyridazine compound (1), Agnique® AMD 810 (a mixture of N,N-dimethyloctane amide and N,Ndimethyldecanamide, 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 the weight ratios 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
Preparation Example No. 5 6 7 8
Present pyridazine compound (1) 8 8 8 8
Agnique® AMD810 10 10 10 10
Phenylsulfonat Cal® 3 3 3 3
Emulsogen® TS290 7 7 7 7
Benzyl alcohol 21.6 36 50.4 57.6
Solvesso® 200ND 50.4 36 21.6 14.4
Benzyl alcohol: Solvesso® 200ND (weight ratio) 30:70 50:50 70:30 80:20
[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 the weight ratios 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
Preparation Example No. 9 10 11 12
Present pyridazine compound (1) 8 8 8 8
Rhodasurf® 860/P 10 10 10 10
Phenylsulfonat Cal® 3 3 3 3
Emulsogen® TS290 7 7 7 7
Benzyl alcohol 21.6 36 50.4 57.6
Solvesso® 200ND 50.4 36 21.6 14.4
Benzyl alcohol: Solvesso® 200ND (weight ratio) 30:70 50:50 70:30 80:20
[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 the weight ratios 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
Preparation Example No. 13 14 15 16
Present pyridazine compound (1) 8 8 8 8
Phenylsulfonat Cal® 3 3 3 3
Emulsogen® TS290 7 7 7 7
Benzyl alcohol 24.6 41 57.4 65.4
Solvesso® 150ND 57.4 41 24.6 16.4
Benzyl alcohol: Solvesso® 30:70 50:50 70:30 80:20
150ND (weight ratio)
[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 the weight ratios 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
Preparation Example No. 17 18 19 20
Present pyridazine compound (1) 8 8 8 8
Phenylsulfonat Cal® 3 3 3 3
Emulsogen® TS290 7 7 7 7
Benzyl alcohol 24.6 41 57.4 65.6
Xylene 57.4 41 24.6 16.4
Benzyl alcohol: Xylene (weight ratio) 30:70 50:50 70:30 80:20
[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), 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 of, 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 Emuisogen® 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 Emuisogen® 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 Emuisogen® 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 Emuisogen® 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), Emuisogen® 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 the weight ratios shown in Table 6, and the mixture was stirred until a homogeneous solution was formed to obtain each of liguid agrochemicals .
[0044]
Table 6
Reference Preparation Example No. 1 2 3
Present pyridazine compound (1) 10 10 10
Phenylsulfonat Cal® 3 3 3
Emuisogen® TS290 7 7 7
Benzyl alcohol 0 16 80
Solvesso® 200ND 80 64 0
Benzyl alcohol: Solvesso® 200ND (weight ratio) 0 :100 20:80 100 : 0
[0045]
Reference Preparation Examples 4 to 6
The present pyridazine compound (1), Agnigue® AMD 810 (a mixture of N,N-dimethyloctane amide and N,Ndimethyldecanamide, manufactured by BASF), Phenylsulfonat
Cal® (calcium dodecylbenzenesulfonate, manufactured by
Clariant), Emuisogen® 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 the weight ratios shown in Table 7, and the mixture was stirred until a homogeneous solution was formed to obtain each of liguid agrochemicals .
[0046] lable 7
Reference Preparation Example No. 4 5 6
Present pyridazine compound (1) 8 8 8
Agnigue® AMD 810 10 10 10
Phenylsulfonat Cal® 3 3 3
Emuisogen® TS290 7 7 7
Benzyl alcohol 0 14.4 72
Solvesso® 200ND 72 57.6 0
Benzyl alcohol: Solvesso® 200ND (weight ratio) 0 :100 20:80 100 : 0
[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), Emuisogen® 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 the weight ratios shown in Table 8, and the mixture was stirred until a homogeneous solution was formed to obtain each of liguid agrochemicals .
[0048]
Table 8
Reference Preparation Example No. 7 8
Present pyridazine compound (1) 8 8
Rhodasurf® 860/P 10 10
Phenylsulfonat Cal® 3 3
Emulsogen® TS290 7 7
Benzyl alcohol 0 72
Solvesso® 200ND 72 0
Benzyl alcohol: Solvesso® 200ND (weight ratio) 0 :100 100 : 0
[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 the weight ratios shown in Table 9, and the mixture was stirred until a homogeneous solution was formed to obtain each of liquid agrochemicals .
[0050]
Table 9
Reference Preparation Example No. 9 10
Present pyridazine compound (1) 8 8
Phenylsulfonat Cal® 3 3
Emulsogen® TS 290 7 7
Benzyl alcohol 0 16.4
Solvesso® 150ND 82 65.6
Benzyl alcohol: Solvesso® 150ND (weight ratio) 0 :100 20:80
[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), parts by weight of Emuisogen® 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 were put into glass tubes, and kept at 0°C. Each of the liquid agrochemicals was kept for 7 days, followed by checking whether there was any crystal precipitation in each of the liquid agrochemicals
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, 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, the state of the liquid in the measuring cylinder was observed visually to evaluate the emulsion stability.
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 remained in a homogeneous emulsified state. On the other hand, crystal precipitation was found on the bottom face of the cylinders with liquids containing each of the liquid agrochemicals obtained in Reference
Preparation Examples 3, 6 and 8.

Claims (8)

Patentkravclaims 1. Flydende agrokemikalie omfattende:A liquid agrochemical comprising: 1 til 11 vægtprocent af en pyridazin-forbindelse af formel1 to 11% by weight of a pyridazine compound of formula R1 er chloratom, bromatom, cyan-gruppe eller methylgruppe; ogR 1 is chlorine atom, bromine atom, cyano group or methyl group; and R2 er hydrogenatom eller fluoratom,R 2 is hydrogen atom or fluorine atom, 1 til 30 vægtprocent af et eller flere overfladeaktive stoffer, og benzylalkohol og et eller flere aromatiske karbonhydrider, hvor det totale indhold af benzylalkohol og det ene eller flere aromatiske karbonhydrid er inden for området på 50 til 98 vægtprocent og vægtforholdet af benzylalkohol til det ene eller flere aromatiske karbonhydrid (benzylalkohol: aromatisk karbonhydrid(er)) er inden for området på 30:70 til 85:15.1 to 30% by weight of one or more surfactants, and benzyl alcohol and one or more aromatic hydrocarbons, wherein the total content of benzyl alcohol and one or more aromatic hydrocarbons is in the range of 50 to 98% by weight and the weight ratio of benzyl alcohol to one or more several aromatic hydrocarbons (benzyl alcohol: aromatic hydrocarbon (s)) are in the range of 30:70 to 85:15. 2. Det flydende agrokemikalie ifølge krav 1, hvor vægtforholdet mellem benzylalkohol og det ene eller flere aromatiske karbonhydrid (benzylalkohol: aromatisk karbonhydrid(er)) er inden for området på 30:70 til 80:20.The liquid agrochemical of claim 1, wherein the weight ratio of benzyl alcohol to one or more aromatic hydrocarbons (benzyl alcohol: aromatic hydrocarbon (s)) is in the range of 30:70 to 80:20. 3. Det flydende agrokemikalie ifølge krav 1 eller 2, hvor det ene eller flere aromatiske karbonhydrid består af mindst ét alkylbenzen eller mindst ét alkylnaftalen.The liquid agrochemical of claim 1 or 2, wherein the one or more aromatic hydrocarbons consists of at least one alkyl benzene or at least one alkyl naphthalene. 4. Det flydende agrokemikalie ifølge et hvilket som helst af kravene 1 til 3, hvor indholdet af pyridazin-forbindelse er inden for området på 4 til 10 vægtprocent.The liquid agrochemical of any one of claims 1 to 3, wherein the content of pyridazine compound is in the range of 4 to 10% by weight. 5. Det flydende agrokemikalie ifølge et hvilket som helst af kravene 1 til 3, hvor indholdet af pyridazin-forbindelsen er inden for området på 4 til 8 vægtprocent.The liquid agrochemical of any one of claims 1 to 3, wherein the content of the pyridazine compound is in the range of 4 to 8% by weight. 6. Det flydende af kravene 1 til en kombination af overfladeaktive stoffer overfladeaktive stoffer.The liquid of claim 1 for a combination of surfactants surfactants. agrokemikalie ifølge et hvilket som helst 5, hvor det overfladeaktive stof omfatter et eller flere ikke-ioniske og et eller flere anioniske og hvilket som helst de overfladeaktive i kombination med polyoxyalkylenan agrochemical according to any of 5, wherein the surfactant comprises one or more nonionic and one or more anionic and any of the surfactants in combination with polyoxyalkylene 7. Det flydende agrokemikalie ifølge et af kravene 1 til 5, hvor det eller stoffer omfatter dodecylbenzensulfonat polyoxyalkylen-polyarylether eller alkylether.The liquid agrochemical according to one of claims 1 to 5, wherein it or substances comprise dodecylbenzenesulfonate polyoxyalkylene polyaryl ether or alkyl ether. 8. Det flydende agrokemikalie ifølge et hvilket som helst af kravene 1 til 7, hvilket er et emulgerbart koncentrat.The liquid agrochemical according to any one of claims 1 to 7, which is an emulsifiable concentrate. IMmsH Fäto? Asm OmaIMmsH Fäto? Asm Grandma SEARCH REPORT - PATENT SEARCH REPORT - PATENT Application No. PA 2017 70156 Application No. PA 2017 70156 1. 1 1 Certain claims were found unsearchable (See Box No. I). 1. 1 1 Certain claims were found unsearchable (See Box No. I). 2. 1 1 Unity of invention is lacking prior to search (See Box No. II). 2. 1 1 Unity of invention is lacking prior to search (See Box No. II). A. CLASSIFICATION OF SUBJECT MATTER A. CLASSIFICATION OF SUBJECT MATTER A 01 N 25/02 (2006.01); A 01 N 43/58 (2006.01) A 01 N 25/02 (2006.01); A 01 N 43/58 (2006.01) According to International Patent Classification (IPC) or to both national classification and IPC According to International Patent Classification (IPC) or to both national classification and IPC B. FIELDS SEARCHED B. FIELDS SEARCHED PCT-minimum documentation searched (classification system followed by classification symbols) PCT minimum documentation searched (classification system followed by classification symbols) IPC/CPC: A01N IPC / CPC: A01N Documentation searched other than PCT-minimum documentation Documentation searched other than PCT minimum documentation DK, NO, SE, FI: IPC-classes as above. DK, NO, SE, FI: IPC classes as above. Electronic database consulted during the search (name of database and, where practicable, search terms used) Electronic database consulted during the search (name of database and, where practicable, search terms used) EPODOC, WPI, FULL TEXT: ENGLISH, GERMAN EPODOC, WPI, FULL TEXT: ENGLISH, GERMAN CAPLUS CAPLUS C. DOCUMENTS CONSIDERED TO BE RELEVANT C. DOCUMENTS CONSIDERED TO BE RELEVANT Category* Citation of document, with indication, where appropriate, of the relevant passages Category * Citation of document, with indication, where appropriate, of the relevant passages Relevant for claim No. Relevant to claim no. A, D EP 1767529 A1 (SUMITOMO CHEMICAL COMPANY, LIMITED (JP)) A, D EP 1767529 A1 (SUMITOMO CHEMICAL COMPANY, LIMITED (JP)) 1-8 1-8 28 March 2007 March 28, 2007 Cited in the application as WO 2005/121104 Cited in the application as WO 2005/121104 See entire document, in particular abstract, paragraphs [0096]-[0100] and [0193]- See entire document, in particular abstract, paragraphs [0096] - [0100] and [0193] - [0199], and claims [0199], and claims 1 δ 1 δ A, D EP 1775290 A1 (SUMITOMO CHEMICAL COMPANY, LIMITED (JP)) A, D EP 1775290 A1 (SUMITOMO CHEMICAL COMPANY, LIMITED (JP)) 18 April 2007 April 18, 2007 Cited in the application as WO 2006/001175 Cited in the application as WO 2006/001175 See entire document, in particular abstract, paragraphs [0085]-[0098] and [0162]- See entire document, in particular abstract, paragraphs [0085] - [0098] and [0162] - [0168], and claims [0168], and claims M Further documents are listed in the continuation of Box C. M Further documents are listed in the continuation of Box C. * Special categories of cited documents: P Document published prior to the filing date but later than the * Special categories of cited documents: P Document published prior to the filing date but later than the A Document defining the general state of the art which is not priority date claimed. A Document defining the general state of the art which is not a priority date claimed. considered to be of particular relevance. T Document not in conflict with the application but cited to considered to be of particular relevance. T Document not in conflict with the application but cited to D Document cited in the application. understand the principle or theory underlying the invention. D Document cited in the application. understand the principle or theory underlying the invention. Έ Earlier application or patent but published on or after the filing date. X Document of particular relevance; the claimed invention cannot beΈ Earlier application or patent but published on or after the filing date. X Document of particular relevance; the claimed invention cannot be considered novel or cannot be considered to involve an inventive considered novel or cannot be considered to involve an inventive L Document which may throw doubt on priority claim(s) or which is when ώ document is taken alone.L Document which may throw doubt on priority claim (s) or which is when ώ document is taken alone . cited to establish the publication date of another citation or other cited to establish the publication date of another citation or other special reason (as specified) Y Document of particular relevance; the claimed invention cannot be special reason (as specified) Y Document of particular relevance; the claimed invention cannot be considered to involve an inventive step when the document is considered to involve an inventive step when the document is ”°” Document referring to an oral disclosure, use, exhibition or other combined with one or more other such documents, such "°" Document referring to an oral disclosure, use, exhibition or other combined with one or more other such documents, such means' combination being obvious to a person skilled in the art. means ' combination being obvious to a person skilled in the art. Document member of the same patent family. Document member of the same patent family. Danish Patent and Trademark Office Date of completion of the search report Danish Patent and Trademark Office Date of completion of the search report Helgeshøj Allé 81 28 September 2017 Helgeshøj Allé 81 September 28, 2017 DK-2630 Taastrnp DK-2630 Taastrnp Denmark Authorized officer Denmark Authorized officer Hans Christian Schiøtz Rudbeck Hans Christian Schiøtz Rudbeck Telephone No.+45 4350 8000 Λ Telephone No. + 45 4350 8000 Λ Facsimile No. +45 4350 8001 1 elePhone No· +45 4350 8125 Facsimile No. +45 4350 8001 1 ele P hone No · + 45 4350 8125
Search ReportSearch Report SEARCH REPORT - PATENT SEARCH REPORT - PATENT Application No. PA 2017 70156 Application No. PA 2017 70156 C (Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT C (Continuation). DOCUMENTS CONSIDERED TO BE RELEVANT Category* Category * Citation of document, with indication, where appropriate, of the relevant passages Citation of document, with indication, where appropriate, of the relevant passages Relevant for claim No. Relevant to claim no. A A EP 1023833 A2 (AMERICAN CYANAMID COMPANY (US)) 08 August 2000 See abstract; paragraphs [0012]-[0018], [0035]-[0036], [0039], and [0051]-[0052]; examples; and claims 1 and 2 EP 1023833 A2 (AMERICAN CYANAMID COMPANY (US)) 08 August 2000 See abstract; paragraphs [0012] - [0018], [0035] - [0036], [0039], and [0051] - [0052]; Examples; and claims 1 and 2 1-8 1-8 A A EP 1025757 A1 (AMERICAN CYANAMID COMPANY (US)) 09 August 2000 See abstract, paragraphs [0034]-[0038] and [0058], and claims 1-6 and 10 EP 1025757 A1 (AMERICAN CYANAMID COMPANY (US)) 09 August 2000 See abstract, paragraphs [0034] - [0038] and [0058], and claims 1-6 and 10 1-8 1-8
Search ReportSearch Report SEARCH REPORT - PATENT SEARCH REPORT - PATENT Application No. PA 2017 70156 Application No. PA 2017 70156 Box No. I Observations where certain claims were found unsearchable Box No. In Observations where certain claims were found unsearchable
This search report has not been established in respect of certain claims for the following reasons: !·□ Claims Nos.:This search report has not been established in respect of certain claims for the following reasons:! □ Claims Nos: because they relate io subject matter not required to be searched, namely:because they relate to subject matter not required to be searched, namely: 2. I I Claims Nos.:2. I I Claims Nos: because they relate to parts of the patent application that do not comply with the prescribed requirements to such an extent that no meaningful search can be carried out, specifically:because they relate to parts of the patent application that do not comply with the prescribed requirements to such an extent that no meaningful search can be performed, specifically: 3. I I Claims Nos.: because of other matters.3. I I Claims Nos .: because of other matters. Box No. II Observations where unity of invention is lacking prior to the searchBox No. II Observations where unity of invention is lacking prior to the search The Danish Patent and Trademark Office found multiple inventions in this patent application, as follows:The Danish Patent and Trademark Office found multiple inventions in this patent application, as follows: Search ReportSearch Report SEARCH REPORT - PATENT SEARCH REPORT - PATENT Application No. PA 2017 70156 Application No. PA 2017 70156 SUPPLEMENTAL BOX SUPPLEMENTAL BOX Continuation of Box [.] Continuation of Box [.]
Search ReportSearch Report
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