FR3048331A1

FR3048331A1 - LIQUID PESTICIDE CONTAINING PYRIDAZINE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE USING THE SAME

Info

Publication number: FR3048331A1
Application number: FR1651818A
Authority: FR
Inventors: Hideo Kawanaka; Yuichi Matsuzaki
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2016-03-04
Filing date: 2016-03-04
Publication date: 2017-09-08
Anticipated expiration: 2036-03-04
Also published as: FR3048331B1

Abstract

L'invention concerne un pesticide liquide dans lequel l'activité de maîtrise des maladies des plantes d'un composé de pyridazine représenté par la formule (I) suivante est augmentée. Le pesticide liquide contient : un composé de pyridazine représenté par la formule (I) suivante un composé d'amide représenté par la formule (II) suivante Ra-CO-NRbRc (II) et un tensioactif. L'invention concerne aussi un procédé de maîtrise des maladies des plantes utilisant ce pesticide.The invention relates to a liquid pesticide in which the plant disease control activity of a pyridazine compound represented by the following formula (I) is increased. The liquid pesticide contains: a pyridazine compound represented by the following formula (I) an amide compound represented by the following formula (II): Ra-CO-NRbRc (II) and a surfactant. The invention also relates to a method of controlling plant diseases using this pesticide.

Description

TECHNICAL AREA

[0001]

The present invention relates to a liquid pesticide containing a pyridazine compound, an amide compound and a surfactant.

STATE OF THE ART

[0002]

Conventionally, a pyridazine compound represented by the following formula (I)

(I) wherein represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and represents a hydrogen atom or a fluorine atom, is known as an active compound for controlling plant diseases (for example see patent document 1 and patent document 2). On the other hand, in the application of an active compound for controlling plant diseases, for reasons of reducing the burden on the environment, guaranteeing the safety of workers, and the like, a study on an agent increasing the effect of causing such an active compound to exhibit a significant effect at lower dose has been achieved (for example, see Patent Document 3). However, the active compounds for controlling plant diseases whose effect can be increased by these effect enhancing agents are currently limited, and in the case of the above pyridazine compound, a combination with a compound having an increasing effect. the plant disease control activity is not known.

PRIOR ART DOCUMENTS PATENT DOCUMENTS

[0003]

Patent Document 1: WO2005 / 121104 Patent Document 2: WO2006 / 001175 Patent Document 3: JP-A-8-337502

SUMMARY OF THE INVENTON PROBLEMS TO BE SOLVED BY THE INVENNON

[0004]

An object of the present invention is to provide a liquid pesticide in which the plant disease control activity of the pyridazine compound is increased.

MEANS TO SOLVE THE PROBLEMS

[0005] Following intensive study to find a liquid pesticide in which the plant disease control activity of the pyridazine compound is increased, the present inventors have found that an amide compound represented by the formula (II) is added to the pyridazine compound, which increases the plant disease control activity of the pyridazine compound.

More specifically, the present invention is as described below.

[1] A liquid pesticide containing: a pyridazine compound represented by the following formula (I)

(I) wherein represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and represents a hydrogen atom or a fluorine atom; an amide compound represented by the following formula (II) ## STR2 ## wherein R is a C 5 -C 17 alkyl group, a C 5 -C 17 alkenyl group or a hydroxyalkyl group; C2 to C4, and R * and R 'are the same or different and are C1 to C3 alkyl; and a surfactant.

[2] The liquid pesticide according to [1], wherein the amide compound represented by the formula (II) is an amide compound wherein R 1 is a C 5 -C 17 alkyl group or a C 2 -C 4 hydroxyalkyl group, and R 1 and R 1 are each methyl.

[3] The liquid pesticide according to [1] or [2], wherein the ratio of the contents of the pyridazine compound represented by the formula (I) to the amide compound represented by the formula (II) is 0.1: 1 to 10: 1 in weight ratio.

[4] The liquid pesticide of any one of [1] to [3], further comprising one or more non-polar solvents selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.

[5] The liquid pesticide of any one of [1] to [4], further comprising an amide ester compound represented by the following formula (III)

(III) wherein is (C2-C5) alkylene, and R '", R1 and R4 are the same or different and are (C1-C3) alkyl.

[6] The liquid pesticide of any one of [1] to [5], which is an emulsifiable concentrate.

[7] A method for controlling plant diseases comprising applying the liquid pesticide as defined in any one of [1] to [6] or an aqueous dilution thereof to wheat, wheat barley or soil to grow wheat or barley. EFFECT OF ΕΊΝΥΕΝΉΟΝ [0006]

According to the present invention, a liquid pesticide in which the plant disease control activity of the pyridazine compound is increased can be provided.

MODES OF REALIZING THE INVENTON

[0007]

The liquid pesticide of the present invention (hereinafter referred to as the pesticide of the present invention) contains a pyridazine compound represented by the following formula (I)

(I) wherein represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and represents a hydrogen atom or a fluorine atom (hereinafter referred to as the present pyridazine compound).

[0008]

Exemplary embodiments of the present pyridazine compound used in the pesticide of the present invention include the following pyridazine compounds.

The pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom or a methyl group; pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom; pyridazine compounds represented by the formula (I), wherein R 1 is a methyl group; pyridazine compounds represented by the formula (I), wherein R 1 is a cyano group; pyridazine compounds represented by the formula (I), wherein R 1 is a hydrogen atom; pyridazine compounds represented by the formula (I), wherein R 1 is a fluorine atom; pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom, a cyano group or a methyl group, and R 1 is a hydrogen atom; pyridazine compounds represented by the formula (I), wherein is a chlorine atom, a cyano group or a methyl group, and is a fluorine atom; pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom, and R 1 is a hydrogen atom or a fluorine atom; pyridazine compounds represented by the formula (I), wherein R 1 is a bromine atom, a cyano group or a methyl group, and R 1 is a hydrogen atom; the pyridazine compounds represented by the formula (I), wherein R 1 is a bromine atom, a cyano group or a methyl group, and R 1 is a fluorine atom.

[0009]

Specifically, examples of present pyridazine compounds include the following.

The pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom, and R 1 is a hydrogen atom (hereinafter referred to as the present pyridazine compound (1)); pyridazine compounds represented by the formula (I), wherein R 1 is a bromine atom, and R 1 is a hydrogen atom (hereinafter referred to as the present pyridazine compound (2)); pyridazine compounds represented by the formula (I), wherein R 1 is a cyano group, and R 1 is a hydrogen atom (hereinafter referred to as the present pyridazine compound (3)); pyridazine compounds represented by formula (I), wherein R 1 is methyl, and R 1 is hydrogen (hereinafter referred to as the present pyridazine compound (4)); pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom, and R 1 is a fluorine atom (hereinafter referred to as the present pyridazine compound (5)); pyridazine compounds represented by the formula (I), wherein is a bromine atom, and is a fluorine atom (hereinafter referred to as the present pyridazine compound (6)); pyridazine compounds represented by the formula (I), wherein R 1 is cyano, and R 1 is fluorine (hereinafter referred to as the present pyridazine compound (7)); the pyridazine compounds represented by the formula (I), wherein R 1 is methyl, and R 1 is a fluorine atom (hereinafter referred to as the present pyridazine compound (8)).

[0010]

Among the present pyridazine compounds, the pyridazine compounds represented by the formula (I), wherein R 1 is a chlorine atom or a bromine atom can be produced, for example, by the method described in WO2005 / 121104.

[0011]

Among the present pyridazine compounds, the pyridazine compounds represented by the formula (I), where R 1 is a methyl group can be produced by the process described in WO2006 / 001175.

[0012]

Among the present pyridazine compounds, the pyridazine compounds represented by the formula (I), wherein R 1 is a cyano group can be produced, for example, by the process described in WO2014 / 013841.

[0013]

The pesticide of the present invention contains the present pyridazine compound in an amount usually from 1 to 30% by weight, preferably from 2 to 20% by weight, and more preferably from 3 to 15% by weight, as a quantity. total, based on 100% by weight of the pesticide of the present invention.

[0014]

The pesticide of the present invention contains an amide compound represented by the following formula (II): ## STR2 ## wherein R 1 is C 5 -C 17 alkyl, alkenyl C5 to C17 or a C2 to C4 hydroxyalkyl group, and and are the same or different, and represent a C1 to C3 alkyl group (hereinafter referred to as the present amide compound).

[0015]

In the present amide compound, the C 5 to C 17 alkyl group means a linear or branched saturated hydrocarbon group having a carbon number of 5 to 17. Examples of C 5 to C 17 alkyl groups include a pentyl group, a neopentyl group, a 2-methylibutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-methylheptyl group, a nonyl group, a 3-ethylheptyl group, a decyl group, a group 3,7-dimethyloctyl, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group and a heptadecyl group.

[0016]

In the present amide compound, the C5 to C17 alkenyl group means a linear or branched unsaturated hydrocarbon group having a number of carbon atoms of 5 to 17. Examples of C5 to C17 alkenyl groups include a group of 1 to 5 carbon atoms. pentenyl, 1-hexenyl, 2-hexenyl, 6-heptenyl, 7-octenyl, 8-nonenyl, 9-decenyl, 2-undecenyl, 3-dodecenyl, a 4-tridecenyl group, a 5-tetradecenyl group, a 6-pentadecenyl group, a 7-hexadecenyl group and an 8-heptadecenyl group.

[0017]

In the present amide compound, the C2-C4 hydroxyalkyl group means a linear or branched saturated hydrocarbon group having a number of carbon atoms of 2 to 4, wherein one or more hydrogen atoms bonded to carbon atoms. carbon are replaced by a hydroxyl group (-OH). Examples of C2-C4 hydroxyalkyl groups include a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-methyl-3-hydroxypropyl group, a 2-methyl-2-hydroxypropyl group, and a 2-hydroxyethyl group. l, l-dimethyl-2-hydroxyethyl.

[0018]

In the present amide compound, the C1 to C3 alkyl group means a linear or branched saturated hydrocarbon group having a number of carbon atoms of 1 to 3. Examples of C1 to C3 alkyl groups include a methyl group, an ethyl group, a propyl group and an isopropyl group.

[0019]

Examples of the present amide compounds include N, N-dimethylhexanamide, N, N-dimethyloctanamide, N, N-dimethyl-decanamide, N, N-dimethyldodecanamide, N, N-dimethylocta-decanamide, N N, N-dimethyl-cis-9-octadecenamide, N, N-dimethyl-lactamide and N, N-diethyldodecanamide.

[0020]

Among the present amide compounds, the present amide compound represented by the formula (II), wherein R is a C 5 to C 17 alkyl group or a C 2 to C 4 hydroxyalkyl group, and and R 1 are one and the other a methyl group, is preferably used. The present preferred amide compound specifically includes one or more amide compounds selected from the group consisting of N, N-dimethyloctanamide, N, N-dimethyldecanamide, N, N-dimethyldodecanamide and N, N-dimethyl- lactamide, one or more amide compounds selected from the group consisting of N, N-dimethyloctanamide, N, N-dimethyldecanamide and N, N-dimethyl-lactamide, and one or more amide compounds selected from the group consisting of N, N-dimethyloctanamide and N, N-dimethyldecanamide.

[0021]

In the present invention, a present commercially available amide compound can be used, and the present commercially available amide compound includes Agnique AMD810 (a mixture of N, N-dimethyloctanamide and N, N-dimethyldecanamide, manufactured by BASF), Agnique AMDIO (N, N-dimethyldecanamide, manufactured by BASF), Agnique AMD12 (N, N-dimethyldodecanamide, manufactured by BASF), Rhodiasolv ADMA810 (a mixture of N, N-dimethyloctanamide and N, N-dimethyl- decanamide, manufactured by Solvay Nicca, Ltd.), Rhodiasolv ADMA-10 (N, N-dimethyldecanamide, manufactured by Solvay Nicca, Ltd.), Hallcomid M-8-10 (N, N-dimethyloctanamide and N, N mixture). dimethyldecanamide, manufactured by Stepan Company), Hallcomid M-10 (N, N-dimethyldecanamide, manufactured by Stepan Company), Hallcomid M-12 (N, N-dimethyl-dodecanamide, manufactured by Stepan Company), Hallcomid M-18 ( N, N-dimethyloctadecanamide, manufactured by Stepan Company), Genagen 4166 (fatty acid dimethylamide, fabr by Clariant), Genagen 4296 (fatty acid dimethylamide, manufactured by Clariant), Hallcomid M-180L (N, N-dimethyl-cis-9-octadecenamide, manufactured by Stepan Company), Agnique AMD3L (N, N-dimethyl) , manufactured by BASF), and the like.

[0022]

The pesticide of the present invention contains the present amide compound in an amount usually from 1 to 40% by weight, and preferably from 3 to 30% by weight, as a total amount, based on 100% by weight. of the pesticide of the present invention.

[0023]

The ratio of the contents of the present pyridazine compound to the present amide compound in the pesticide of the present invention is usually 0.1: 1 to 10: 1, preferably 0.2: 1 to 5. 1, and more preferably 0.3: 1 to 4; 1 in weight ratio.

[0024]

The pesticide of the present invention contains a surfactant. The surfactant includes nonionic surfactants, anionic surfactants, cationic surfactants and ampholytic surfactants.

[0025]

Examples of nonionic surfactants include a polyoxyethylene polyoxypropylene block copolymer; polyalkoxylated fatty acid esters such as a polyethoxylated fatty acid ester and a polyethoxylated polypropoxylated fatty acid ester; polyalkoxylated alkyl ethers such as a polyethoxylated alkyl ether and a polyethoxylated polypropoxylated alkyl ether; polyalkoxylated polyarylethers such as polyethoxylated tristyrylphenyl ether, polyethoxylated polyarylether and polypropoxylated polyethoxylated polyarylether; polyalkoxylated alkylarylethers such as polyethoxylated alkylarylethers and polypropoxylated polyethoxylated alkylarylethers; polyalkoxylated vegetable oils such as polyethoxylated castor oil and polypropoxylated polyethoxylated castor oil; hardened polyalkoxylated vegetable oils such as hardened polyethoxylated castor oil; fatty acid and glycerol esters; fatty acid and sorbitan esters such as sorbitan laurate, sorbitan stearate, sorbitan oleate and sorbitan trioleate; and polyaryoxylated fatty acid and sorbitan esters such as polyethoxylated sorbitan laurate, polyethoxylated sorbitan stearate, polyethoxylated sorbitan oleate, and polyethoxylated sorbitan trioleate. Of the above nonionic surfactants, a polyalkoxylated alkyl ether is preferably used.

[0026]

Examples of anionic surfactants include alkylarylsulfonates such as dodecylbenzenesulfonate; dialkylsulfosuccinates such as di (2-ethylhexyl) sulfosuccinate; polyaryloxy polyarylether sulphates such as polyethoxylated distyrylphenyl ether sulphate; polyalkylated polyarylether phosphates such as polyethoxylated tristyrylphenyl ether phosphate; polyaryloxy alkylaryl ether phosphates such as a polyethoxylated alkylarylether phosphate; and polyalkoxylated alkyl ether phosphates such as a polyethoxylated alkyl ether phosphate. Examples of salts in sulfonates, sulfates and phosphates include sodium salts, potassium salts, calcium salts and ammonium salts. Of the above anionic surfactants, calcium dodecylbenzenesulfonate is preferably used.

[0027]

Examples of cationic surfactants include alkylamine hydrochlorides such as dodecylamine hydrochloride; quaternary alkyl ammonium salts such as dodecyltrimethylammonium salts, alkyldimethylbenzylammonium salts, alkylpyridinium salts, alkylisoquinolinium salts and dialkylmorpholinium salts; benzethonium chloride; and polyalkylvinylpyridinium salts.

[0028]

Examples of ampholytic surfactants include N-lauryl-alanine, Ν, Ν, Ν-trimethylaminopropionic acid, Ν, Ν, Ν-trihydroxyethylaminopropionic acid, N-hexyl-N, N-dimethylamino acid and the like. acetic acid, betaine 1- (2-carboxyethyl) pyridinium and lecithin.

[0029]

In the present invention, a surfactant composed of a combination of one or more nonionic surfactants and one or more anionic surfactants is preferably used, and the ratio of the contents of one or more anionic surfactants to one or more surfactants. Nonionic is more preferably in the range of 1: 0.1 to 1: 10 by weight.

[0030]

In the present invention, a commercially available nonionic surfactant can be used, and examples of commercially available nonionic surfactants include Toximul 8323 (a polyoxyethylene polyoxypropylene block copolymer, manufactured by Stepan Company), Atlas G5002L (a block copolymer). butyl, manufactured by Croda International Pic), PEGNOL 24-0 (polyethoxylated fatty acid ester, manufactured by TOHO Chemical Industry Co., Ltd.), PEGNOL 14-S (polyethoxylated fatty acid ester, manufactured by TOHO Chemical Industry Co., Ltd.), PEGNOL ST-7 (polyethoxylated alkyl ether, manufactured by TOHO Chemical Industry Co., Ltd.), ATPLUS245 (polyethoxylated polypropoxylated alkyl ether manufactured by Croda International Pic), Synperonic AB6 (polyalkoxylated alkyl ether, HLB: 12, manufactured by Croda International Pic), Brij 03 (polyethoxylated oilyl ether, HLB: 7, manufactured by Croda International Pic), Emulsogen TS200 (polyethoxylated tristyrylphenyl ether), manufactured by Clariant), SORPOL T26 (polyethoxylated alkylarylether, manufactured by TOHO Chemical Industry Co., Ltd.), Alkamuls OR / 40 (polyethoxylated castor oil, manufactured by Solvay Nicca, Ltd.), NIKKOL HCO-20 (polyethoxylated castor oil) cured, manufactured by Nikko Chemicals Co., Ltd.), NIKKOL MGU (fatty acid ester of glycerol, manufactured by Nikko Chemicals Co., Ltd.), NIKKOL DGS-80 (fatty acid ester of glycerol, manufactured by Nikko Chemicals Co., Ltd.), Newcol 20 (sorbitan laurate, manufactured by NIPPON NYUKAZAI CO., LTD.) and Newcol 25 (polyethoxylated sorbitan laurate, manufactured by NIPPON NYUKAZAI CO., LTD.).

[0031]

In the present invention, a commercially available anionic surfactant may be used, and examples of commercially available anionic surfactants include Rhodacal 70 (branched calcium dodecylbenzene sulfonate, manufactured by Solvay Nicca, Ltd.), Rhodacal 70 / B (Linear calcium dodecylbenzenesulfonate, manufactured by Solvay Nicca, Ltd.), Rhodacal LDS-25 / AP (linear sodium dodecylbenzenesulfonate, manufactured by Solvay Nicca, Ltd.), Calsogen 4814 (calcium dodecylbenzenesulfonate, manufactured by Clariant), Geropon CYA Sodium bis (2-ethylhexyl) sulfosuccinate, manufactured by Solvay Nicca, Ltd.), Soprophor DSS / 7 (polyethoxylated distyrylphenyl ether sulfate, ammonium salt, manufactured by Solvay Nicca, Ltd.), Soprophor FLK (tristyrylphenyl ether phosphate). polyethoxylated potassium, manufactured by Solvay Nicca, Ltd.), Rhodafac PS / 17 (polyethoxylated alkylarylether phosphate, manufactured by Solvay Nicca, Ltd.) and Phosphanol RD-720 (alkylated). polyethoxylated sodium phosphate, manufactured by TOHO Chemical Industry Co., Ltd.).

[0032]

The pesticide of the present invention contains the surfactant in an amount usually from 1 to 25% by weight, preferably from 3 to 15% by weight, and more preferably from 5 to 15% by weight, as a total amount, on the basis of 100% by weight of the pesticide of the present invention. In a further preferred embodiment, the pesticide of the present invention contains the nonionic surfactant in an amount of 1 to 15% by weight, and contains the anionic surfactant in an amount of 1 to 10% by weight. In a particularly preferred embodiment, the pesticide of the present invention contains the nonionic surfactant in an amount of 3 to 10% by weight, and contains the anionic surfactant in an amount of 2 to 6% by weight.

[0033]

The pesticide of the present invention preferably further contains one or more non-polar solvents (hereinafter referred to as the present non-polar solvent) selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons, and an aromatic hydrocarbon is preferably still used.

[0034]

Examples of aromatic hydrocarbons include xylene, ethylbenzene, octadecylbenzene, dodecylnaphthalene, tridecyl-naphthalene and phenylxylylethane. Examples of aliphatic hydrocarbons include decane, tridecane, tetradecane, hexadecane, octadecane, normal paraffin, isoparaffin, cycloparaffin, 1-undecene and 1-heneicosene.

[0035]

In the present invention, a present commercially available non-polar solvent can be used, and examples of present commercially available non-polar solvents include Nisseki Hisol SAS-296 (1-phenyl-1-xylylethane and 1-phenyl-1-xylylethane mixture). phenyl-1-ethylphenylethane, manufactured by JX Nippon Oil & Energy Corporation), SOLVESSO 100 (mainly C9 to C10 dialkyl- and trialkylbenzene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical

Company), SOLVESSO 150 (mainly CIO to Cyl alkylbenzene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical

Company), SOLVESSO 150ND (mainly CIO to Cyl alkylbenzene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical

Company), SOLVESSO 200 (mainly CIO to C14 alkylnaphthalene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical

Company) and SOLVESSO 200ND (mainly C11-C14 alkylnaphthalene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical Company).

[0036]

When the pesticide of the present invention contains the present non-polar solvent, the total content is usually 5 to 60% by weight, and preferably 10 to 50% by weight, based on 100% by weight of the pesticide of the present invention. .

[0037]

The pesticide of the present invention preferably further contains an amide ester compound represented by the following formula (III)

Wherein R '' is C 2 -C 5 alkylene, and R '', R '' and R '' are the same or different and represent a C 1 -C 6 alkyl group; at C3 (hereinafter referred to as the present amide ester compound) This is because the stability of the pesticide of the present invention is improved by addition of the present amide ester compound.

[0038]

In the present amide ester compound, the C1 to C3 alkyl group means a linear or branched saturated hydrocarbon group having a number of carbon atoms of from 1 to 3. Examples of C1 to C3 alkyl groups include a methyl group an ethyl group, a propyl group and an isopropyl group.

[0039]

In the present amide ester compound, the C 2 -C 5 alkylene group means a linear or branched divalent saturated hydrocarbon group having a number of carbon atoms of 2 to 5. Examples of C 2 -C 5 alkylene groups include a group ethylene, a propylene group, a trimethylene group, a butylene group, a tetramethylene group, a 2-methyltrimethylene group and a pentamethylene group.

[0040]

Among the present amide ester compounds, the present amide ester compound represented by the formula (III) wherein is a tetramethylene group, a butylene group or a 2-methyltrimethylene group, and any one of R '", R and R 1 is methyl is preferably used The present preferred amide ester compound specifically includes methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate.

[0041]

In the present invention, a commercially available amide ester compound can be used, and the present commercially available amide ester compounds include Rhodiasolv Polarclean (containing 80 to 90% by weight of 5- (dimethylamino) - Methyl 2-methyl-5-oxopentanoate (based on a total amount of 100% by weight), manufactured by Solvay Nicca, Ltd.

[0042]

When the pesticide of the present invention contains the present amide ester compound, the total content is usually 10 to 60% by weight, and preferably 15 to 50% by weight, based on 100% by weight of the pesticide of the present invention. present invention.

[0043]

The pesticide of the present invention may further contain an active compound for controlling plant diseases different from the present pyridazine compound. Examples of active compounds controlling plant diseases different from the present pyridazine compound include: azole compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazoie, diniconazole, bromuconazole , repoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, ripconazole, simeconazole, hymexazol, etridiazole, flutriafol, [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (R); ) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, the 2 - {[3 - (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H- 1.2.4- triazol-3-thione, 2 - {[rel- (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro -3H-1,2,4-triazol-3-thione, 2 - {[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl ] -methyl} -2,4-dihydro-3H-1,2,4-triazol-3-thione, 2 - {[(2R, 3S) -3- (2-chloro-phenyl) -2- 4-difluorophenyl) oxiran-2-yl] methyl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, the 2 - {[(2S, 3R) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, the 2 - {[(2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazol-3-thione, the 2 - {[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-2,4- triazol-3-thione, 1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxilan-2-yl] methyl} -1H-1,2,4-triazol-5-thiol, 1 - {[rel- (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluoro-phenyl) oxiran-2-yl] methyl} -1H-1,2,4 triazol-5-thiol, 1 - {[rel "(2R, 3R) -3" (2-chlorophenyl) -2- (2,4-dif) luorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-thiol, 1 - {[(2R, 3S) -3- (2-chlorophenyl) -2- -difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-thiol, 1 - {[(2S, 3R) -3- (2-chloro-phenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-thiol, 1 - {[(2R, 3R) -3- (2-chlorophenyl) -2 - (2,4-Difluorophenyl) oxiran-2-yl] methyl] -1H-1,2,4-triazol-5-thiol, 1 - {[(2S, 3S) -3- (2-chlorophenyl) 2- (2,4-Difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-thiol, 1 - {[3- (2-chlorophenyl) -2 thiocyanate - (2,4-difluorophenyl) oxiran-2-yl] methyl] -1H-1,2,4-triazol-5-yl, thiocyanate of 1 - {[rel- (2R, 3S) -3- (2 2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, thiocyanate of 1 - {[rel- (2R, 3R) 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, thiocyanate of 1 - {[(( 2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, the thiocyanate of {[(2S, 3R) -3- (2-chlorop henyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, thiocyanate of 1 - {[(2R, 3R) -3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] -methyl} -1H-1,2,4-triazol-5-yl, thiocyanate of 1 - {[(2S, 35 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, 5- (4-chlorobenzyl); 2-Chloromethyl-2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1RS, 2SR, 5SR) -5- (4-chlorobenzyl) -2-chloromethyl -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1RS, 2RS, 5RS) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1 (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1RS, 2RS, 5SR) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1), 2,4-triazol-1-ylmethyl) cyclopentanol, (1RS, 2SR, 5RS) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol) 1-ylmethyl) cyclopentanol, (1R, 2S, 5S) -2-chloromethyl-5- (4-fluoro-benzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1S, 2R, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1 R, 2 R, 5 R) -2-chloromethyl-5- (4-fluoro-benzyl) -2-methyl 1- (1H-1,2,4-Triazol-1-ylmethyl) cyclopentanol, (1S, 2S, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H- 1,2,4-triazol-1-ylmethyl) cyclopentanol, (1 R, 2 R, 5 S) -2-chloromethyl-5- (4-fluoro-benzyl) -2-methyl-1- (1H-1,2), 4-triazol-1-ylmethyl) cyclopentanol, (1S, 2S, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol) -1- ylmethyl) cyclopentanol, (1R, 2S, 5R) -2-chloromethyl-5- (4-fluoro-benzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1S, 2R, 5S) -2-Chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, 2-chloromethyl (1- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1RS, 2SR, 5SR) -2-chloro-methyl-5- ( 4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) -cyclopentanol, (1RS, 2RS, 5RS) -2-chloromethyl-5- (4-fluorobenzyl) - 2-methyl-l- (lH-l, 2,4-triazol-l-ylmethyl) cyclopentanol, (1RS, 2RS, 5SR) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, ( 1RS, 2SR, 5RS) -2-chloromethyl-5- (4-fluoro-benzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1R, 2S, 5S) -2-Chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1S, 2R, 5R) -2-chloromethyl (1- (4-Fluoro-benzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1 R, 2 R, 5 R) -2-chloromethyl-5- ( 4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1S, 2S, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2 methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1R, 2R, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- ( 1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1S, 2S, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2), 4-triazol-1-ylmethyl) cyclopentanol, (1 R, 2 S, 5 R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol) -1- ylmethyl) cyclopentanol, the (1S, 2R, 5S) -2-chlo romethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-trlazol-1-ylmethyl) cyclopentanol, (2- [2-chloro-4- (4-chlorophenoxy) phenyl) 1- (1,2,4-Triazol-1-yl) pent-3-yn-2-ol, 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- ( 1,2,4-triazol-1-yl) -propan-2-ol, 1- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1-cyclopropyl-2- (1,2) 4-Triazol-1-yl) ethanol, 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -3-methyl-1- (1,2,4-tetrazol-1-yl) butan-2-ol, (R) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1,2,4-trlazol-1-yl) pent-3-yn-2 (R) -2- [4- (4-Chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1,2,4-triazol-1-yl) propan-2-ol, R) -1- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1-cyclopropyl-2- (1,2,4-triazol-1-yl) ethanoI and the (R) -2- [4- (4-Chloro-phenoxy) -2- (trifluoromethyl) phenyl] -3-methyl-1- (1,2,4-triazol-1-yl) butan-2-ol; carboxamide compounds such as bixafen, benzovindiflupyr, fluxapyroxad, penthiopyrad, N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazol-4-carboxylic acid amide , (R) - (-) - N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazol-4-carboxylic acid amide, the acid amide ( S) - (+) - N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazol-4-carboxylic acid, a mixture of R enantiomer and S enantiomer (98: 2 ) of N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazol-4-carboxylic acid amide, isofetamid, isopyrazam, boscalid, fluopyram, sedaxane, penflufen, flutolanil, mepronil, carboxin, thifluzamide, furametpyr, N-cyclopropyl-5-fluoro-3- (difluoromethyl) -N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole 4-carboxamide, N- (5-chloro-2-isopropylbenzyl) -N-cyclo-propyl-5-fluoro-3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- [ l- (2,4-dichlorophenyl) -l-methoxypropan-2-yl] -3 difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N - [(1R, 2R) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-yl; methyl-1H-pyrazole-4-carboxamide, N - [(1R, 25) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole 4-carboxamide, N - [(1S, 2R) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N - [(1S, 2S) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, the rel-N- [(1 R, 2 R) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, rel-N - [(IR 25) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N - [(1R, 2R5) -l (- (2,4-dichloro-phenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N - [(15,2R5) -1- (2) 4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide. N - [(1R5,2R) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N - [( 1RS, 25) -1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, 3-difluoromethyl-N-methoxy-1 methyl-N- [1-methyl-2- (2,4,6-trichloro-phenyl) ethyl] pyrazole-4-carboxamide, 3-difluoromethyl-N-methoxy-1-methyl-N - [(1 R) 1-methyl-2- (2,4,6-trichlorophenyl) ethyl] -pyrazole-4-carboxamide and 3-difluoromethyl-N-methoxy-1-methyl-N - [(1S) -1-methyl-2 - (2,4,6-trichlorophenyl) ethyl] pyrazole-4-carboxamide; Qol compounds such as azoxystrobin, pyraclostrobin, picoxystrobin, trifloxystrobin, mandestrobin, fluoxastrobin, kresoxim-methyl, dimoxystrobin, orysastrobin, metominostrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, triclopyricarb , fenaminstrobin, pyribencarb, famoxadone, and fenamidone; fenpropimorph, fenpropidine, spiroxamine, 5-amino-4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole, 5-amino-4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole. amino-4- (2-bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole, 5-amino-4- (2-chloro-4-fluorophenyl) ) -N- (2-chloro-6-fluoro-phenyl) -1,3-dimethyl-1H-pyrazole, 5-amino-4- (2-bromo-4-fluorophenyl) -N- (2-chloro) -N 6-fluorophenyl) -1,3-dimethyl-1H-pyrazole, 5-amino-4- (2-chloro-4-fluorophenyl) -N- (2,6-difluoro-4-methylphenyl) -1,3- dimethyl-1H-pyrazole, 5-amino-4- (2-bromo-4-fluorophenyl) -N- (2,6-difluoro-4-methylphenyl) -1,3-dimethyl-1H-pyrazole, 5- Amino-N- (2-chloro-6-fluoro-4-methylphenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole, 5-amino-4- (2- bromo-4-fluorophenyl) -N- (2-chloro-6-fluoro-4-methyl-phenyl) -1,3-dimethyl-1H-pyrazole, (3S, 6S, 7R, 8R) -2-methylpropanoate 3 - {[(3-hydroxy-4-methoxy-2-pyrldlnyl) carbonyl] amino} -6-methyl-4,9-d-oxo-8- (phenylmethyl methyl!) -l, 5-dloxonan-7-! yle, the 2-m {[4-methoxy-2 - ({[(3S, 7R, 8R, 9S) -9-methyl-8- (2-methyl-1-oxopropoxy) -2,6-dioxo-7- (phenylmethyl) ethylpropanoate) 1- [5-dloxonan-3-yl] amino] carbonyl) -3-pyridinyl] oxy} methyl, N '- [4 - ({3 - [(4-chlorophenyl) methyl] -1,2,4 -thiadiazol-5-yl} oxy) -2,5-dinethylphenyl] -N-ethyl-N-methyl-imidamide and 2,6-dimethyl-1H, 5H- [1,4] dithiino [2,3-c] : 5,6-c '] dipyrrole-l, 3,5,7 (2H, 6H) -tetrone.

[0044]

When the pesticide of the present invention contains an active compound for controlling plant diseases different from the present pyridazine compound, the total content is usually 1 to 50% by weight, preferably 2 to 30% by weight, and more preferably 3 to 30% by weight. at 15% by weight, based on 100% by weight of the pesticide of the present invention.

[0045]

The pesticide of the present invention may further contain an auxiliary organic solvent (with the exception of the present amide compounds, the present amide ester compounds, aromatic hydrocarbons and aliphatic hydrocarbons). Examples of auxiliary organic solvents include: alcohols such as ethanol, isopropanol, butanol, octanol, cyclohexanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol; esters such as methyl laurate, methyl salicylate, methyl oleate, ethyl acetate, ethyl palmitate, octyl acetate, benzyl acetate, dimethyl phthalate, 2-methylglutaric acid dimethyl ester, 2-ethylsuccinic acid dimethyl ester, dimethyl adipate, diethyl oxalate, dioctyl succinate, didecyl adipate, propylene glycol diacetate, acetoacetate, tert-butyl, allyl acetoacetate, acetic acid 1-methyl-2-methoxyethyl ester, 2-butoxyethyl acetate, methyl lactate, ethyl lactate and 2-ethylhexyl lactate; ethers such as bis- [2- (2-methoxyethoxy) ethyl] ether, bis (2-ethoxyethyl) ether, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and monophenyl ether. propylene glycol; ketones such as methyl diethyl ketone, cyclohexanone and acetophenone; lactones such as γ-butyrolactone, γ-valerolactone and ε-caprolactone; lactams such as N-octyl caprolactam, N-decyl caprolactam, N-dodecyl caprolactam, N-methylpyrrolidone, N-octylpyrrolidone, N-decylpyrrolidone, N-dodecyl- pyrrolidone, N-octyl-valerolactam, N-decyl-valerolactam and N-dodecyl-valerolactam; imidazolidinones such as 1,3-dimethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone and 1,3-diisopropyl-2-imidazolidinone; cyclic urea derivatives such as N, N'-dimethylpropyleneurea; carbonic acid esters such as ethylene carbonate and propylene carbonate; fatty acids such as oleic acid, capric acid and heptanoic acid; animal and vegetable oils such as olive oil, soybean oil, rapeseed oil, castor oil, linseed oil, cottonseed oil, palm oil avocado oil and shark liver oil; mineral oils such as machine oil.

[0046]

In the present invention, a commercially available auxiliary organic solvent can be used, and the commercially available auxiliary organic solvent includes Rhodiasolv Iris (a mixture of dimethyl 2-methylglutarate, dimethyl 2-ethylsuccinate and dimethyl adipate). , manufactured by Solvay Nicca, Ltd.), PURASOLV ML (L-methyl lactate, manufactured by Corbion purac), PURASOLV EL (L-ethyl lactate, manufactured by Corbion purac), PURASOLV EHL (L-lactate 2- ethylhexyl, manufactured by Corbion purac), Jeffsol AG-1555 (propylene carbonate, manufactured by Huntsman International LLC.), and the like.

[0047]

When the pesticide of the present invention contains an auxiliary organic solvent, the total content is usually 1 to 60% by weight, and preferably 5 to 50% by weight, based on 100% by weight of the pesticide of the present invention.

[0048]

Some examples of pesticides of the present invention are presented below. Here, the content of each component is 1% by weight based on 100% by weight of the pesticide of the present invention.

Example 1 of pesticide of the present invention

A liquid pesticide containing 1 to 30% by weight of any compound of the present pyridazine compound (1) to the present pyridazine compound (8), 1 to 40% by weight of N, N-dimethylhexanamide, 5 to 60% by weight the weight of the present non-polar solvent and 1 to 25% by weight of a surfactant.

Examples 2 to 13 of pesticides of the present invention

Liquid pesticides containing the present amide compounds shown below in place of N, N-dimethylhexanamide in Example 1 of the pesticide of the present invention.

Example 2 of the pesticide of the present invention N, N-dimethyloctanamide

Example 3 of the pesticide of the present invention N, N-dimethyldecanamide

Example 4 of the pesticide of the present invention N, N-dimethyldodecanamide

Example 5 of the present invention N, N-dimethyloctadecanamide

Example 6 of the present invention N, N-dimethyl-cis-9-octadecenamide

Example 7 of the pesticide of the present invention N, N-dimethyl lactam

Example 8 of the present invention N, N-diethyldodecanamide

Example 9 of pesticide of the present invention

Agnique AMD810

Example 10 of the pesticide of the present invention Rhodiasolv ADMA810

Example 11 of pesticide of the present invention Hallcomid M-8-10

Example 12 of the pesticide of the present invention Genagen 4166

Example 13 of the pesticide of the present invention Genagen 4296

Examples 14 to 26 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of an anionic surfactant and 1 to 15% by weight of a nonionic surfactant as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention .

Examples 27 to 39 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyoxyethylene polyoxypropylene block copolymer as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention. present invention.

Examples 40 to 52 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyethoxylated tristyrylphenyl ether as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention .

Examples 53 to 65 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyethoxylated fatty acid ester as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention.

Examples 66 to 78 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyethoxylated alkyl ether as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention .

Examples 79 to 91 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyethoxylated alkylarylether as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention .

Examples 92 to 104 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyethoxylated castor oil as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention. present invention.

Examples 105 to 117 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a fatty acid and sorbitan ester as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention.

Examples 118 to 130 of pesticides of the present invention

Liquid pesticides containing 1 to 10% by weight of calcium dodecylbenzenesulfonate and 1 to 15% by weight of a polyalkoxylated fatty acid and sorbitan ester as 1 to 25% by weight of surfactant in Examples 1 to 13 of pesticides of the present invention.

Examples 131 to 260 of pesticides of the present invention

Liquid pesticides additionally containing 10 to 60% by weight of Rhodiasolv Polarclean in Examples 1 to 130 of pesticides of the present invention.

Examples 261 to 520 of pesticides of the present invention

Liquid pesticides containing SOLVESSO 200ND as the present nonpolar solvent in Examples 1-260 of pesticides of the present invention.

Examples 521 to 1040 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of propiconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 1041 to 1560 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of prothioconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 1561 to 2080 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of tebuconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 2081-2600 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of flusilazole in Examples 1 to 520 of pesticides of the present invention.

Examples 2601 to 3120 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of bromuconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 3121-3640 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of epoxiconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 3641 to 4160 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of cyproconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 4161 to 4680 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of metconazole in Examples 1 to 520 of pesticides of the present invention.

Examples 4681 to 5200 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of bixafen in Examples 1 to 520 of pesticides of the present invention.

Examples 5201 to 5720 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of benzovindiflupyr in Examples 1 to 520 of pesticides of the present invention.

Examples 5721 to 6240 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of fluxapyroxad in Examples 1 to 520 of pesticides of the present invention.

Examples 6241 to 6760 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of penthiopyrad in Examples 1 to 520 of pesticides of the present invention.

Examples 6761 to 7280 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazole-4-carboxylic acid amide in Examples 1 to 520 of pesticides of the present invention.

Examples 7281 to 7800 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of (R) - (-) - N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethyl-pyrazole acid amide -4-carboxylic acid in Examples 1 to 520 of pesticides of the present invention.

Examples 7801-8320 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of a mixture of enantiomer R and S (98: 2) enantiomer of N- (1,1,3-trimethylindan-4-yl) acid amide 1-methyl-3-difluoromethylpyrazole-4-carboxylic acid in Examples 1 to 520 of pesticides of the present invention.

Examples 8321-8840 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of isopyrazam in Examples 1 to 520 of pesticides of the present invention.

Examples 8841 to 9360 of pesticides of the present invention

Liquid pesticides additionally containing from 1 to 50% by weight of boscalid in Examples 1 to 520 of pesticides of the present invention.

Examples 9361 to 9880 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of azoxystrobin in Examples 1 to 520 of pesticides of the present invention.

Examples 9881-10400 of pesticides of the present invention

Liquid pesticides additionally containing 1 to 50% by weight of pyraclostrobin in Examples 1 to 520 of pesticides of the present invention.

[0049]

The pesticide of the present invention may take different forms of preparations provided that it is in liquid form, and is preferably an emulsifiable concentrate.

[0050]

When the pesticide of the present invention is an emulsifiable concentrate, for example, it can be produced by dissolving the present pyridazine compound in a mixture containing the present amide compound and a surfactant, and as necessary, the present compound. amide ester, the present non-polar solvent, an auxiliary organic solvent, and the like.

[0051]

The pesticide of the present invention can be used to control a plant disease.

[0052]

The pesticide of the present invention can control plant diseases by applying the pesticide to a plant or a soil for growing a plant. The method of applying the pesticide of the present invention is not particularly limited provided that the pesticide of the present invention can be substantially applied, and the exemplary methods include application to a plant such as foliage and application to a crop field of a plant, such as ground application.

[0053]

The pesticide of the present invention is applied in such a way that the application rate of the present pyridazine compound is usually 1 to 500 g, and preferably 2 to 200 g per 1000 m 2 although it may be modified according to the conditions types of formulations, timing of application, method of application, area of application, target diseases, target plant, and the like. An emulsifiable concentrate is usually applied after dilution with water, and the concentration of the present pyridazine compound in the water-diluted liquid is usually 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight.

[0054]

Examples of plant diseases that can be controlled by the pesticide of the present invention include rice diseases: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi; wheat diseases: Erysiphe graminis, Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P. recondita, Micronectriella nivale, Typhula sp., Ustilago tritici, Tilletia caries, Pseudocercosporella herpotrichoides, Mycosphaerella graminicola, Stagonospora nodorum, Pyrenophora tritici-repentis; barley diseases: Erysiphe graminis, Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale, Puccinia striiformis, P.graminis, P.hordei, Ustilago nuda, Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Rhizoctonia solani; corn diseases: Ustilago maydis, Cochliobolus heterostrophus, Gloeocercospora sorghi, Puccinia polysora, Cercospora zeae-maydis, Rhizoctonia solani; Soy diseases: Cercospora kikuchii, Einsinoe glycines, Diaporthe phaseolorum var. soybean, Septoria glycines, Cercospora sojina, Phakopsora pachyrhizi, Phytophthora soya, Rhizoctonia solani, Corynespora cassiicola, Sclerotinia scierotiorum; bean diseases: Colletotrichum lindemthianum; diseases of the potato: Alternaria solani, Phytophthora infestans, Phytophthora erythroseptica, Spongospora subterranean f. sp. subterranea; rape diseases: Sclerotinia scierotiorum, Rhizoctonia solani; cotton diseases: Rhizoctonia solani, Mycosphaerella areola, Thielaviopsis basicola; diseases of sugar cane: Puccinia melanocephela, Puccinia kuehnii, Ustilago scitaminea; sunflower diseases: Puccinia helianthi; diseases of sugar beet: Cercospora beticola, Thanatephorus cucumeris, Thanatephorus cucumeris, Aphanomyces cochlioides; and banana diseases: Mycosphaerella fijiensis, Mycosphaerella musicola.

[0055]

Examples of target plants of the pesticide of the present invention include field crops: maize, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanut , buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, solanaceous plants (eggplant, tomato, green pepper, pepper, potato, etc.), cucurbit vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), cruciferous plants (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, etc.), composite plants (burdock, hedychium, chrysanthemum, artichoke, lettuce, etc.), lily plants (spring onions) onions, garlic, asparagus, etc.), umbelliferous plants (carrots, parsley, celery, parsnips, etc.), chenopodiac vegetables (spinach, etc.), labial plants (Japanese mint, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc .; flowers; foliage plants; quackgrass; fruit trees; pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince, etc.), fleshy stone fruit (peach, plum, nectarine, Japanese plum, cherry , apricot, prune plum, etc.), citrus (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut , almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), vine, persimmon, olive , loquat, banana, coffee, date, coconut, etc .; and trees other than fruit trees: tea trees, mulberry trees, Jatropha (Jatropha curcas), flowering trees and shrubs, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, Judas tree, sweet gum tree, plane tree, zeikova, Japanese tree of life, fir, Japanese fir-hemlock, needle juniper, pine, spruce, yew), and application to wheat and barley is preferred.

[0056]

The plant can be a plant produced by hybrid technology. The plant produced by hybrid technology is a plant with a characteristic of heterosis (generally resulting in increased yield potential, improved resistance to biological and non-biological stressors, and the like).

[0057]

Also, the plant may be a plant to which resistance has been conferred by gene recombination technology.

EXAMPLES

[0058]

The present invention is described below in detail with reference to the following examples.

[0059]

Production examples 1 to 11

The raw materials indicated in Table 1 were mixed in the weight ratios shown in Table 1, and stirred until the mixture became a uniform solution to obtain the emulsifiable concentrates (hereinafter referred to as EC) 1 to 11. of the present invention. Here, the numbers in the table represent parts by weight.

[Table 1]

The trade names shown in Table 1 are as described below.

Agnique AMD810: Mixture of N, N-dimethyloctanamide and N, N-dimethyldecanamide, manufactured by BASF;

Hallcomid M-8-10: Mixture of N, N-dimethyloctanamide and N, N-dimethyldecanamide, manufactured by Stepan Company;

Agnique AMD3L: N, N-dimethyl-lactamide, manufactured by BASF; SOLVESSO 200ND: Primarily C11-C14 alkylnaphthalene as aromatic hydrocarbon, manufactured by ExxonMobil Chemical Company; Calsogen 4814: Calcium dodecylbenzenesulfonate manufactured by Clariant; ATPLUS245: polyethoxylated polypropoxylated alkyl ether manufactured by Croda International Pic;

Brij 03: polyethoxylated oleyl ether, HLB: 7, manufactured by Croda International Pic;

Atlas G5002L: butyl block copolymer, manufactured by Croda International Pic;

Toximul 8323: polyoxyethylene polyoxypropylene block copolymer, manufactured by Stepan Company;

Rhodiasolv Polarclean: Containing 80 to 90% by weight of methyl 5- (dimethyl-amino) -2-methyl-5-oxopentanoate (based on a total amount of 100% by weight), manufactured by Solvay Nicca, Ltd . PURASOLV ML: L-methyl lactate, manufactured by Corbion purac; PURASOLV EL: L-ethyl lactate, manufactured by Corbion purac; [0061]

Examples of reference production 1 to 3

The raw materials indicated in Table 2 were mixed in the weight ratios shown in Table 2, and the same procedures as in Production Examples 1 to 11 were used to obtain Comparative CEs 1 to 3. Here, the numbers in the table represent parts by weight.

[Table 2]

The trade names shown in Table 2 are as described above.

[0063]

Test example 1

Soil was introduced into a plastic pot, and wheat (variety: Apogee) was sown in it, and grown in a greenhouse for 10 days. An EC was diluted with water so that the dosage of the present pyridazine compound per hectare was 90 g (200 L per hectare of the soil surface area in the treated pot), and sprayed over of the pot in which the wheat was planted. After spraying, the wheat was air-dried, and after 4 days a wheat septoria fungus was inoculated with wheat by spraying an aqueous suspension of the spores of the fungus. This is called a treatment section. On the other hand, wheat was grown in the same manner as in the treatment section except that the EC diluted with water was not sprayed, and a wheat septoria blight was inoculated with wheat. by spraying an aqueous suspension of spores of the fungus. This is called a section without treatment.

After inoculation, the plant was first placed at 18 ° C under high humidity for 3 days and was further placed under illumination for 14 to 18 days, then the lesion area was examined, and the Mastery value was calculated according to the following formula. The test was repeated twice, and the average value is shown in Table 3.

Mastery (%) = (l- (lesion area in the treatment section / lesion area in the untreated section)) x 100 [0064] [Table 3]

[0065]

Test example 2

Soil was introduced into a plastic pot, and wheat (variety: Apogee) was sown in it, and grown in a greenhouse for 10 days. A wheat septoria fungus was inoculated with wheat by spraying with an aqueous suspension of spores of the fungus, the wheat was placed at 18 ° C under high humidity for 3-4 days, and then air-dried. An EC was diluted with water so that the dosage of the present pyridazine compound per hectare was 60 g (200 L per hectare of the soil surface area in the treated pot), and sprayed above of the pot in which the wheat was planted. After spraying, the wheat was air dried. This is called a treatment section. On the other hand, wheat was grown in the same manner as in the treatment section except that the EC diluted with water was not sprayed, and a wheat septoria blight was inoculated with wheat. by spraying an aqueous suspension of spores of the fungus. This is called a section without treatment.

The plant was placed under illumination for 10 to 14 days, then the lesion area was examined, and the control value was calculated according to the following formula. The test was repeated twice, and the average value is shown in Table 4.

Mastery (%) = (l- (lesion area in the treatment section / lesion area in the untreated section)) x 100 [0066] [Table 4]

[0067]

Test example 3

Soil was introduced into a plastic pot, and wheat (variety: Apogee) was sown in it, and grown in a greenhouse for 10 days. An EC was diluted with water so that the dosage of the present pyridazine compound per hectare was 60 g (200 L per hectare of the soil surface area in the treated pot), and sprayed above of the pot in which the wheat was planted. After spraying, the wheat was air-dried, and after one day exposed to rain at 20 mm per hour for 3 hours using an artificial rainfall device. In addition, after 3 days, a wheat septoria fungus was inoculated with wheat by spraying an aqueous suspension of spores of the fungus. This is called a treatment section. On the other hand, wheat was grown in the same manner as in the treatment section except that the EC diluted with water was not sprayed, and a wheat septoria blight was inoculated with wheat. by spraying an aqueous suspension of spores of the fungus. This is called a section without treatment.

After inoculation, the plant was first placed at 18 ° C under high humidity for 3 days and was further placed under illumination for 14 to 18 days, then the lesion area was examined, and the Mastery value was calculated according to the following formula. The test was repeated twice, and the average value is shown in Table 5.

Mastery (%) = (l- (lesion area in the treatment section / lesion area in the untreated section)) x 100 [0068] [Table 5]

[0069]

Test example 4 (storage stability at low temperature)

The ECs 6 and 7 of the present invention were each stored at -5 ° C for 3 months, and the change in appearance was observed. Both EC 6 and 7 of the present invention were both transparent and clear liquid even after storage, and precipitation deposition and the like were not found.

[0070]

Test Example 5 (self-emulsification property, emulsion stability)

In a 100 ml capped test tube were charged with 99 ml of CIPAC D standard water (hardness: 342 ppm) at 30 ° C, and 1 ml of EC was slowly added dropwise from about 8 cm above the surface of the water. The state of an EC droplet in water was visually observed to evaluate the autoemulsification property. Then, the test piece was plugged, and a reversal operation of the test piece of 180 ° in 1 second, and reversal in 1 second was repeated 10 times. Then, the test piece was allowed to stand in a water bath at a constant temperature of 30 ° C for 2 hours, after which the emulsion state of the diluted liquid was visually observed to evaluate the stability of the emulsion. . The criteria for evaluating the self-emulsification property and the stability of the emulsion are presented below. <<Self-emulsifyingproperty>> 1: The droplet self-emulsifies and disappears before reaching the bottom of the test tube. 2: The droplet self-emulsifies but reaches the bottom of the test tube. 3: The droplet does not self-emulsify and precipitates at the bottom of the test tube. <<Stability of the emulsion >> 1: A separation of cream, oil and the like is absolutely not caused. 2: A separation of a small amount (less than 1 ml) of cream or oil is caused. 3: Separation of a large amount (1 ml or more) of cream or oil is caused.

[Table]

Claims

REVENDICATONS

1. A liquid pesticide characterized in that it contains: a pyridazine compound represented by the following formula (I)

(I) wherein represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and R 1 represents a hydrogen atom or a fluorine atom; an amide compound represented by the following formula (II)

(II) wherein R® is (C5-C17) alkyl, (C5-C17) alkenyl or (C2-C4) hydroxyalkyl, and R1 and R1 are the same or different and are (C1-C6) alkyl; at C3; and a surfactant.

The liquid pesticide according to claim 1, characterized in that the amide compound represented by the formula (II) is an amide compound wherein R is a C 5 to C 17 alkyl group or a C 2 to C 4 hydroxyalkyl group and R 1 and R 1 are each methyl.

3. Liquid pesticide according to claim 1 or 2, characterized in that the ratio of the contents of the pyridazine compound represented by the formula (I) to the amide compound represented by the formula (II) is 0.1: 1 to 10 : 1 in weight ratio.

4. Liquid pesticide according to any one of claims 1 to 3, characterized in that it further comprises one or more non-polar solvents selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.

5. Liquid pesticide according to any one of claims 1 to 4, characterized in that it further comprises: an amide ester compound represented by the following formula (III)

(III) wherein is (C2-C5) alkylene, and R ", R" and R4 are the same or different and are (C1-C3) alkyl.

6. Liquid pesticide according to any one of claims 1 to 5, characterized in that it is an emulsifiable concentrate.

7. Process for controlling plant diseases, characterized in that it comprises the application of the liquid pesticide according to any one of claims 1 to 6 or an aqueous dilution thereof to wheat, wheat or barley or soil to grow wheat or barley.