WO2019163946A1 - Phytotoxicity reducing agent containing bactericidal compound as active ingredient, and phytotoxicity-reduced herbicidal composition containing said phytotoxicity reducing agent and herbicidal compound - Google Patents

Abstract

This phytotoxicity reducing agent contains, as an active ingredient, at least one compound selected from the group consisting of hydroxyisoxazole, picarbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate-methyl, isoprothiolane, and amisulbrom, or a salt thereof.

Description

A safener having an antibacterial compound as an active ingredient, and a herbicidal composition with a safener comprising the safener and herbicidal compound

The present invention relates to a safener. More specifically, the present invention relates to a phytotoxicity reducing agent containing a bactericidal compound as an active ingredient, and a phytotoxicity-reduced herbicidal composition comprising the phytotoxicity reducing agent and a herbicidal compound.

The use of herbicides is indispensable in the cultivation of crops in order to secure an appropriate yield of the crops and to realize efficient cultivation of the crops. Currently, the herbicides used are given selectivity to the crops, and except for the plants to be controlled, the crops are not damaged in principle.

However, the crop selectivity of the herbicide is not always sufficient, and depending on the use conditions of the herbicide, the growth failure, growth suppression, growth suppression, brown spot appearance, and tillering suppression of the crop by the herbicide May cause known or unknown undesirable phytotoxicity such as yellowing, leaf wilt, withering, wilting, whitening, torsion, browning, root growth inhibition and the like.

So far, in order to avoid such phytotoxicity, combined use of herbicides having different actions, combined use of a compound (Safener) having a phytotoxicity-reducing effect and herbicides (Patent Documents 1 to 4) 4, Non-Patent Document 1).

Compounds selected from the group consisting of hydroxyisoxazole, picalbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane, and amisulbrom are known fungicidal compounds, and each compound is shown in Table 1 below. As described in the corresponding patent literature.

In the past, it has been reported that 3-hydroxy-5-isoxazole (hereinafter referred to as “hydroxyisoxazole”), which is a bactericidal compound, has an effect of reducing herbicide phytotoxicity in rice (Non-patent Document 2).

In addition, it is known that the isothiazole carboxamides, which are resistance inducers, have a herbicidal phytotoxicity-reducing effect by applying seed treatment and seedling box application (Patent Documents 16 to 18).

Further, isoprothiolane having bactericidal activity and insecticidal activity is known to have a phytotoxicity-reducing effect on tefryltrione, which is a herbicide (Patent Document 19).

Japanese Unexamined Patent Publication No. 2016-40235 WO2010 / 070822 WO2011 / 145318 WO2011 / 145329 Japanese Patent Publication No.42-25660 WO2003 / 016303 JP-A-1-131163 Japanese Patent Publication No.42-6818 US Pat. No. 3,290,353 US Pat. No. 3,631,176 US Patent 4020095 Japanese Examined Patent Publication No. 47-34126 Japanese Patent No. 4438919 JP 2001-187786 A Japanese Patent Laying-Open No. 2005-112738 JP-T-2001-522840 JP 2004-346030 A JP 2007-137833 A JP 2008-69091 A

However, these conventional safeners are compounds that have herbicidal activity or compounds that do not have biological activity (herbicidal activity, bactericidal activity, insecticidal activity, etc.) when used alone. By limiting to cultivated plants, the phytotoxicity by the herbicide was reduced only about the specific herbicide. Therefore, existing safeners cannot be universally used for various cultivated crops (Patent Documents 1 to 4, Non-Patent Document 1).

Specifically, herbicides that have been confirmed to be effective in reducing the phytotoxicity of hydroxyisoxazole, which is a bactericidal compound, include cimetrin and DCPA (propanil; Dimethyl 2,3,5,6-tetrachlorobenzene-1,4- Mainly photosynthesis inhibiting herbicides such as dicarboxylate), MCC (swep), MCP (ethyl 2-methyl-4-chlorophenoxyacetate). Therefore, no knowledge has been obtained regarding the phytotoxicity-reducing effects of herbicides developed in recent years.

In addition, with regard to isoprothiolane, although herbicide phytotoxicity reduction against tefryltrione is known, no knowledge has been obtained regarding the phytotoxicity reduction effect against other herbicides.

Furthermore, the herbicide damage-reducing effects of fungicidal compounds having bactericidal activity such as picalbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane and amisulbrom have not been clarified at present.

The subject of the present invention has biological activity other than the herbicidal effect, exhibits a phytotoxicity-reducing effect for various herbicides that exhibit different actions, and has an excellent phytotoxicity-reducing effect on cultivated plants than the existing phytotoxicity-reducing agents, And it is to find a novel safening agent with a wide range of use in which cultivated plants are not limited.

As a result of various studies to solve the above-mentioned problems, the present inventors have found that a predetermined fungicidal compound exhibits a herbicide phytotoxicity reducing effect. That is, the present inventors have found that a phytotoxicity reducing agent containing a predetermined bactericidal compound as an active ingredient and a herbicidal composition containing the phytotoxicity reducing agent and a herbicidal compound have a good phytotoxicity reducing effect, and have completed the present invention.

That is, the present invention is as follows [1]-[19].
[1] For crops containing, as an active ingredient, at least one compound selected from the group consisting of hydroxyisoxazole, picalbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane and amisulbromine as an active ingredient Safener.
[2] The safener according to [1], wherein the active ingredient is hydroxyisoxazole, picalbutrazox, amisulbrom or a salt thereof.
[3] The crop is rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, green beans, pea, broad bean, azuki bean, strawberry, cabbage, Japanese radish, mibuna, mizuna, turnip, nabana, Chinese cabbage, broccoli, cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, iris The phytotoxicity-reducing agent according to any one of [1] and [2], which is chrysanthemum, fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
[4] The safener according to any one of [1] to [3], wherein the crop is rice.
[5] A herbicidal composition comprising at least one herbicidal compound or a salt thereof and a safener for a crop according to any one of [1] to [4].
[6] The herbicidal compound is at least one herbicidal compound or a salt thereof selected from the group consisting of the following (A1) to (A6):
(A1) ACCase-inhibiting herbicidal compound,
(A2) an acetolactate synthase-inhibiting herbicidal compound,
(A3) Whitening type herbicidal compound,
(A4) VLCFA-inhibiting herbicidal compound,
(A5) Protopolyfilinogen IX oxidase-inhibiting herbicidal compound,
(A6) synthetic auxin herbicidal compound,
The herbicidal composition according to [5], wherein the active ingredient contained in the safener is at least one compound selected from the group consisting of hydroxyisoxazole, picarbutrazox and amisulbrom or a salt thereof. object.
[7] The crop is rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, green beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, nabana , Chinese cabbage, broccoli, cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, The herbicidal composition according to [5] or [6], which is iris, chrysanthemum, fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
[8] The herbicidal composition according to any one of [5] to [7], wherein the crop is rice.
[9] The method according to any one of [5] to [8], wherein the herbicidal compound is at least one herbicidal compound selected from the group consisting of the following (A2) and (A3) or a salt thereof. Herbicidal composition.
(A2) an acetolactate synthase-inhibiting herbicidal compound,
(A3) Whitening type herbicidal compound.
[10] The herbicidal composition according to [9], wherein the herbicidal compound is at least one herbicidal compound or a salt thereof selected from the group consisting of the following (A2-1) and (A3-1): .
(A2-1) sulfonylurea herbicidal compound, pyrimidinylbenzoic acid herbicidal compound or triazolopyrimidine herbicidal compound,
(A3-1) A pyrazole herbicidal compound or a triketone herbicidal compound.
[11] A method for reducing phytotoxicity to crops by an application method selected from the group consisting of the following (B1) to (B4).
(B1) A method in which the phytotoxicity reducing agent a according to any one of [1] to [4] and the herbicidal composition b not containing the phytotoxicity reducing agent are mixed and applied,
(B2) A method of independently applying the safener a in any one of [1] to [4] and the herbicidal composition b not containing the safener to the same crop,
(B3) The phytotoxicity reducing agent a according to any one of [1] to [4] and the herbicidal composition c according to any one of [5] to [10] are independently applied to the same crop. how to,
(B4) A method of applying the herbicidal composition c according to any one of [5] to [10].
[12] The safener a, the herbicidal composition b, or the herbicidal composition c is treated to the plant body and / or seed, or applied to the soil and / or treated to the root or the rhizome of the plant body. [11] A method for reducing phytotoxicity.
[13] The method for reducing phytotoxicity according to [12], wherein the treatment on the seed is spraying, smearing, dipping, powdering or spraying on the seed.
[14] The method for reducing phytotoxicity according to [12], wherein the application to soil is treatment to paddy soil, treatment to the soil surface, irrigation to soil, or mixing with soil.
[15] The crop is rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, green beans, pea, broad bean, azuki bean, strawberry, cabbage, Japanese radish, mibuna, mizuna, turnip, nabana, Chinese cabbage, blocky, cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, pepper, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honeybee, ginger, arabic, tobacco, carnation, iris [11] The method of reducing phytotoxicity according to [11], which is chrysanthemum, fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
[16] The method for reducing phytotoxicity according to [11] or [15], wherein the crop is rice.
[17] The application method selected from the group consisting of (B1) to (B4) is performed once or twice on the plant body before transplantation, or once on the soil and / or the root or rhizome of the plant body. Or the method of reducing the phytotoxicity as described in [11] performed twice.
[18] In the application method of (B2), the safener agent a is applied once or twice to the plant body before transplanting, and the herbicidal composition b not containing the safener agent is transplanted into the soil and / or Or the method applied to a plant body, The said crop is rice, The method of reducing the phytotoxicity as described in [11] or [17].
[19] The safener a is hydroxyisoxazole, picalbutrazox, amisulbrom or a salt thereof, and the herbicidal composition b is selected from the group consisting of the above (A2-1) and (A3-1) The method for reducing phytotoxicity according to [11], [17] or [18], which is at least one herbicidal compound or a salt thereof.

The present invention is based on the finding that the bactericidal compound exhibits a herbicide phytotoxicity-reducing effect. That is, according to the present invention, a disease control effect derived from bactericidal activity can be expected by treating a phytotoxicity-reducing agent before and after herbicide treatment or at the time of herbicide treatment, and universally applied to various cultivated crops. Can be used effectively, and a good phytotoxicity reduction effect can be obtained.

Next, various terms used in this specification will be explained.

“Damage mitigation agent” means that when agricultural materials are used in cultivated crops to control weeds and pests, growth damage, growth suppression, growth suppression, brown spot appearance, and tillering suppression are reduced. , Yellowing, leaf blight, withering, wilting, whitening, torsion, browning, root growth inhibition, etc., when known or unknown undesired phytotoxicity is expected, use together with agricultural materials or use agricultural materials It is a composition that reduces its phytotoxicity by single use before and after.

The salt of “a compound selected from the group consisting of hydroxyisoxazole, picarbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane, and amisulbromine” refers to a metal salt, an acid addition salt, etc. of the compound. For example, alkali metal salts such as lithium, sodium, potassium, for example, alkaline earth metal salts such as calcium, barium, magnesium, for example, aluminum salts or transition metal salts such as manganese, copper, zinc, iron, for example, Hydrohalic acid salts such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, for example, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, such as methanesulfone Acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benze Salts of sulfonic acids such as sulfonic acid and p-toluenesulfonic acid, such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, Examples include salts of carboxylic acids such as ascorbic acid, lactic acid, gluconic acid, and citric acid, and salts of amino acids such as glutamic acid and aspartic acid.

“ACCase-inhibiting herbicidal compound” refers to, for example, allyloxypropionic acid-based compounds, cyclohexadione oxime-based compounds, and the like, for example, propaxahop, quizalofop, haloxyhop, fluazifopbutyl, fluazifop-P-butyl. , Cihalohop butyl, clodinahop propargyl, diclohop methyl, phenoxaprop-P-ethyl, butroxidim, propoxydim, cretodim, tepraxidim, tolalkoxydim, cetoxydim, cycloxydim, pinoxaden and the like.

“Acetolactate synthase-inhibiting herbicidal compound” refers to, for example, sulfonylurea compounds, sulfonylaminocarbonyltriazolinone compounds, pyrimidinylbenzoic acid compounds, triazolopyrimidine compounds, imidazolinone compounds, and the like. For example, amidosulfuron, azimusulfuron, trifloxysulfuron, bensulfuronmethyl, cyclosulfamuron, flupirsulfuronmethyl, forumsulfuron, chlorimuronethyl, etamethsulfuronmethyl, halosulfuronmethyl, nicosulfuron, Chlorsulfuron, ethoxysulfuron, imazosulfuron, oxasulfuron, pyrazosulfuron ethyl, tritosulfuron, synosulfuron, frazasulfuron, iodosulfuron methyl, primisul Ron methyl, rimsulfuron, thifensulfuron methyl, mesosulfuron methyl, metsulfuron methyl, prosulfuron, trisulfuron, triflusulfuron methyl, sulfosulfuron, tribenuron methyl, trifloxysulfuron, flucetsulfuron, metazosulfuron, Propyrisulfuron, Flucarbazone, Propoxycarbazone, Bispyribac, Pyribenzoxim, Pyrithiobac, Pyriphthalide, Pyriminobacmethyl, Pyrimyrphan, Triamon, Chloransrammethyl, Diclosram, Floraslam, Flumethoslam, Methoslam, Penoxsulam, Imazapic, Imazapyr, Imazapyr Metabenzmethyl, imazaquin, imazamox, imazetapill, etc., preferably azimusulfuron, benz Freon methyl, halosulfuron methyl, imazosulfuron, pyrazosulfuron ethyl, flucetosulfuron, metazosulfuron, propyrisulfuron, bispyrivac, pyriftalide, pyriminobacmethyl, pyrimisulfurphan, triamon, penoxsulam, and more preferably imazosulfuron, Pyrimisul fans.

The “whitening type herbicidal compound” refers to, for example, a pyrazole compound, a triketone compound, and the like. For example, pyrazolate, pyrazoxifene, benzophenap, pyrasul photole, topramone, tolpyralate, mesotrione, sulcotrione, benzobicyclo , Tefryltrione, tembotrione, bicyclopyrone, lancotrione, cyclopyrimolate, fenquinotrione, etc., preferably pyrazolate, pyrazoxifene, benzophenap, mesotrione, sulcotrione, benzobicyclone, tefryltrione , Lancotrione, cyclopyrimolate, fenquinotrione, and the like, and more preferably sulcotrione, tefryltrione, and the like.

The “VLCFA-inhibiting herbicidal compound” refers to, for example, a chloroacetamide compound and the like, for example, acetochlor, butachlor, alachlor, dimetachlor, dimethenamide, propachlor, tenyl chlor, metazachlor, metolachlor, S-metolachlor , Pretilachlor, petoxamide, mefenacet, fenfentrol, fentolazamide, ipfencarbazone, phenoxasulfone, and the like.

“Protopolyfilinogen IX oxidase-inhibiting herbicidal compound” refers to, for example, a diphenyl ether compound, a triazolinone compound, and the like, for example, acifluophene, bifenox, fomesafen, lactophene, oxyfluorfen, carfentrazone ethyl, Sulfentrazone, pentoxazone, pyraclonyl, oxadiazone, oxadialgyl and the like.

The “synthetic auxin-based herbicidal compound” refers to, for example, a phenoxycarboxylic acid-based compound and the like, for example, chromeprop, MCPA, MCPB, 2,4-DB, and fluoropyraloxifene benzyl.

The term “crop” as used in the present invention refers to a plant that protects and manages human propagation and growth. Crop is categorized by comprehensively judging its cultivation method, commercial value, purpose of use, use part, botany classification, etc. Generally, crops are roughly classified into agricultural crops and horticultural crops. The
Agricultural crops are divided into food crops, craft crops, feed crops, and green manure crops according to the purpose of use. Specifically, for example, rice, wheat, barley, potato, corn, grape, apple, pear, peach, nectarine, ume, apricot, sweet potato, oyster, quince, quince, chestnut, cui fruit, blueberry, loquat, banana, Citrus, fig, olive, papaya, akebi, oil palm, soybean, peanut, green beans, pea, broad bean, azuki bean, strawberry, cabbage, Japanese radish, mikona, mibuna, turnip, komatsuna, Chinese cabbage, broccoli, cauliflower, nabana, lettuce, non-headed Lettuce, tomato, eggplant, bell pepper, capsicum, gangan, leek, onion, scallop, cucumber, bitter melon, melon, watermelon, pumpkin, zucchini, carrot, ginger, ginger, burdock, udo, taranki, spinach, sugar beet Lagas, okra, seri, safflower, rapeseed, honeybee, sweet potato, taro, yam, konjac, sugar cane, tobacco, tea, coffee, sunflower, tulip, carnation, basil, iris, aster, rose, chrysanthemum, cotton, pop, gentian, Lily, Button, Peonies, Cyclamen, Pepper, Pepper, Garlic, Buffalo, Perilla, Cinnamon, Wasabi, Taranki, Lotus root, Sorghum, Western turf (Bentgrass, Bermudagrass, Bluegrass, Ryegrass), Japanese turf, Orchardgrass, Italian ryegrass , Alfalfa, red clover, valerian, mulberry, celosia, physalis, calendula, safflower, azalea, cherry blossom, oak, bokeh, poplar, velvet, ginseng, trees, timber (seedlings) It is.
Among them, rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugar cane, potato, grape, soybean, kidney beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, nabana, Chinese cabbage, broccoli, cauliflower , Lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, iris, chrysanthemum, fig, Citrus, timber (seedlings), western turf (bentgrass, ryegrass, bluegrass), Japanese turf, etc. are preferred. Rice, sugar beet, western turf, Japanese turf, wheat, barley, corn, rapeseed, cotton, sunflower, sugar cane, potato More preferably such dough, but rice is particularly preferred, but the invention is not limited thereto.

The “plant” in the present invention is a general term for all parts constituting the “crop”, and examples thereof include stems, leaves, roots, seeds, flowers, fruits and the like.
The “seed” as used in the present invention refers to a seed that stores nutrients for germination of young plants and is used for agricultural propagation. Specifically, for example, seeds such as corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, green pepper, rape, potato, potato, etc. , Seed potatoes such as sweet potato and konjac, edible lily, bulbs such as tulips, and seed balls such as raccoon, etc .; it is a plant produced by artificially manipulating genes, etc., and does not exist in nature Genetically modified crops; for example, soybeans, corn, cotton, etc. that have been given herbicide tolerance, adapted to cold regions, such as rice, tobacco, etc .; or, for example, seeds of corn, cotton, etc., that have been given the ability to produce insecticides, potatoes Tuber etc., but is not limited to these .

Next, a phytotoxicity-reducing agent comprising the fungicidal compound of the present invention as an active ingredient, and a phytotoxicity-reduced herbicidal composition containing the phytotoxicity-reducing agent and a herbicidal compound will be described.

First, the phytotoxicity reducing agent containing the bactericidal compound of the present invention as an active ingredient will be described.
The safener of the present invention comprises, as an active ingredient, at least one compound selected from the group consisting of hydroxyisoxazole, picarbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane, and amisulbrom. contains.
What are the active ingredients? From the viewpoint of the effect of the present invention, hydroxyisoxazole, picalbutrazox, amisulbrom or a salt thereof is preferable.

The phytotoxicity reducing agent of the present invention may be used as it is, but is usually used by mixing with a carrier, and if necessary, a surfactant, a binder, a disintegrant, a stabilizer, a pH adjuster, an antibacterial agent. Add adjuncts such as antifungal agents (preservatives), thickeners, antifoaming agents, wetting agents, fixing agents, coloring agents, etc., according to conventional methods, timely, wettable powder, flowable powder, granular wettable powder , OD agents, powders, liquids, emulsions, granules, packs, and the like. The dosage form is not limited to those compositions as long as the effect is exhibited.

The carrier used in the safener of the present invention is a synthetic or natural compound formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transport and handling of the active ingredient compound. As long as it is an inorganic or organic substance and is usually used for agricultural and horticultural agents, it can be used in either solid or liquid form and is not limited to a specific one.

Examples of the solid carrier that can be used for the safener of the present invention include inorganic substances such as bentonite, montmorillonite, diatomaceous earth, white clay, talc and clay; plant organic substances such as wood flour and sawdust; Can be mentioned.

Examples of the liquid carrier that can be used for the safener of the present invention include aromatic hydrocarbons such as toluene; naphthenes; paraffinic hydrocarbons such as n-paraffin, liquid paraffin, and kerosene; acetone and methyl ethyl ketone. Ketones such as dioxane and diethylene glycol dimethyl ether; alcohols such as ethanol and ethylene glycol; carbonates such as ethylene carbonate; aprotic solvents such as dimethylformamide; and water.

Furthermore, in order to enhance the efficacy of the safener of the present invention, it is possible to use adjuvants, either alone or in combination, depending on the purpose, taking into consideration the dosage form, processing method, etc. of the preparation. . Examples of the adjuvant include surfactants, binders, disintegrants, stabilizers, pH adjusters, antibacterial / antifungal agents, thickeners, antifoaming agents, antifreeze agents and the like.

As the surfactant that can be used for the safener of the present invention, a surfactant that is usually used for the purpose of emulsifying, dispersing, spreading, and / or wetting the agricultural chemical preparation can be used. Such as, for example, sorbitan fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polyoxypropylene block polymer Nonionic interfaces such as ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene bisphenyl ethers, polyoxyalkylene adducts of higher alcohols and polyoxyethylene ethers and ester type silicones and fluorosurfactants Active agent;
Alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene benzyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, paraffin sulfonate, alkane sulfonate, AOS, dialkyl sulfosuccinate, alkylbenzene sulfonate, lignin sulfonate, polyoxyethylene alkylphenyl Ether sulfonate, fatty acid salt, N-methyl-fatty acid sarcosinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene phenyl ether phosphate, polyoxyethylene polyoxypropylene block polymer phosphate, phosphatidylcholine, phosphatidylethanolimine, alkyl phosphate, tripoly Anionic surfactants such as sodium;
A polyanionic polymer surfactant derived from acrylic acid, acrylonitrile, and acrylamidomethylpropanesulfonic acid;
Cationic surfactants such as alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, benzethonium chloride;
Alternatively, amphoteric surfactants such as dialkyldiaminoethyl bentine and alkyl dimethyl benzyl bentine are listed.

Examples of the binder include sodium alginate, polyvinyl alcohol, gum arabic, carboxymethyl cellulose (hereinafter referred to as “CMC sodium”), bentonite and the like.

Examples of the disintegrant include CMC sodium and croscarmellose sodium.

Examples of the stabilizer include hindered phenol-based antioxidants; or benzotriazole-based and hindered amine-based ultraviolet absorbers.

Examples of the pH adjuster include phosphoric acid, acetic acid, sodium hydroxide and the like.

Examples of the antibacterial / antifungal agent include industrial bactericides such as 1,2-benzisothiazolin-3-one, and antibacterial / antifungal agents.

Examples of the thickener include xanthan gum, guar gum, sodium CMC, gum arabic, polyvinyl alcohol, montmorillonite and the like.

Examples of antifoaming agents include silicone compounds.

Examples of the antifreezing agent include propylene glycol and ethylene glycol.

The adjuvants described above are examples, and the adjuvant of the present invention is not limited to the above.

The content of the active ingredient in the safener of the present invention is usually in the range of 0.1 to 100% by weight, preferably in the range of 0.1 to 90%, more preferably 1 It is in the range of ˜80%, particularly preferably in the range of 5 to 50%.

The phytotoxicity reducing agent of the present invention can exert an effect on various phytotoxicity to cultivated crops, for example, phytotoxicity to crops caused by herbicidal compounds, for example, growth disorder, growth inhibition, growth inhibition, appearance of brown spots It is possible to reduce phytotoxicity such as tillering suppression, yellowing, leaf wilt, withering, wilting, whitening, torsion, browning, root growth inhibition and the like.
Especially the phytotoxicity reducing agent of this invention is especially excellent in the phytotoxicity suppression effect with respect to the crop resulting from a herbicidal compound.

The phytotoxicity reducing agent comprising the fungicidal compound of the present invention as an active ingredient is phytotoxicity to crops caused by the herbicidal compound, for example, growth disorder, growth inhibition, growth inhibition, appearance of brown spots, tillering inhibition, yellowing, It is possible to avoid leaf blight, death, wilting, whitening, torsion, browning, root growth inhibition, and the like.
Examples of target crops include rice, wheat, barley, potato, corn, grape, apple, pear, peach, nectarine, ume, apricot, sweet potato, oyster, quince, quince, chestnut, cucumber fruit, blueberry, loquat, banana, citrus , Figs, olives, papaya, akebi, oil palm, soybean, groundnut, green beans, peas, green peas, broad bean, azuki bean, strawberry, cabbage, radish, mizuna, mibuna, turnip, komatsuna, Chinese cabbage, broccoli, cauliflower, nabana, lettuce, tomato , Eggplant, pepper, capsicum, tougan, leek, onion, scallop, cucumber, bitter melon, melon, watermelon, pumpkin, zucchini, carrot, ginger, ginger, burdock, ud, taranki, spinach, sugar beet, Sparagas, okra, seri, safflower, rapeseed, honeybee, sweet potato, taro, yam, konjac, sugar cane, tobacco, tea, coffee, sunflower, tulip, carnation, basil, iris, aster, rose, chrysanthemum, cotton, pop, gentian, Lily, Button, Peonies, Cyclamen, Pepper, Pepper, Garlic, Buffalo, Perilla, Cinnamon, Wasabi, Taranki, Lotus root, Sorghum, Western turf (Bentgrass, Bermudagrass, Bluegrass, Ryegrass), Japanese turf, Orchardgrass, Italian ryegrass , Alfalfa, red clover, valerian, mulberry, celosia, physalis, calendula, safflower, azalea, cherry blossom, oak, bokeh, poplar, velvet, ginger, tree, timber (seedling), etc. And the like.
Among them, rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugar cane, potato, grape, soybean, kidney beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, nabana, Chinese cabbage, broccoli, cauliflower , Lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, iris, chrysanthemum, fig, Citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass), Japanese turf are preferred, rice, sugar beet, western turf, Japanese turf, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, en More preferably such c, rice is particularly preferred

In the present invention, rice refers to an annual plant of the genus Oryza, and is classified into two ecotypes, japonica species (O. sativa subsp. Japonica) and indica species (O. sativa subsp. Indica). The Starch, the main component of the edible portion of rice, is classified into amylose and amylopectin due to the difference in molecular structure, and varieties containing about 20% amylose are cultivated (粳), and the amylose content is 0% due to genetic defects. Varieties that are categorized as Mochi (ち). As specific varieties, for example, Koshihikari, Nipponbare, Akitakomachi, Kirara 397, Kinuhikari, Hitomebore, Nanatsuboshi, Hoshinoyume, Haenuki, Domannaka, Sasanishiki and Hinohikari etc. As the low amylose varieties, for example, Aya, Taisho, Koganemochi, Miyakoganemochi, Asahi Kaoru, Fujikura Kaoru, Hiyokumochi, Himenomochi, Mochihikari, Yume no Hachimochi, Hakuchomochi, Toyohatamochi, Wataboshi, etc. , Milky Queen, Dream Gotchi, Ikuhikari, Milky Pearl, Himenomochi, etc. are sake brewing suitable rice, for example, Yamada Nishiki, Hyakumangoku, Miyama Nishiki, Omachi, Hachiso, Hachimannishiki, Ginfu, Yumesansa, Wakamizu For fodder, dream incense, ferry, etc., for example, Hoshiyutaka, Hoshiaoba, Kusanohoshi, Kusayutaka, Nichiaoba And Southern Yutaka, and the like. In addition, upland rice, black rice, red rice, green rice and special varieties bred using disease resistance and insect resistance as an index, herbicide resistance, insecticidal effect, pest resistance by classical breeding methods or genetic recombination techniques Also included are varieties that have been given sex.

In the present invention, target crops include rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, green beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip , Nabana, cabbage, broccoli, cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, red pepper, tobacco, Carnation, iris, chrysanthemum, fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf are preferred. The phytotoxicity reducing agent of the present invention is particularly excellent in the effect of reducing phytotoxicity caused by herbicidal compounds in these crops.

The safener that contains the fungicidal compound of the present invention as an active ingredient can also be used for controlling plant diseases caused by the original fungicidal activity. As diseases that can be controlled,
For example, rice blast (Magnaporthe grisea), blight blight (Thanatephorus cucumeris), brown sclerotia (Ceratobasidium setariae), brown sclerotia nuclei (Waiteria circinata), brown rot eucalyptus (T) Disease (Sclerotium hydrophilum), red sclerotia (Wairrea circinata), scab (Entyloma dactylidis), staphylococcal sclerotia (Magnaporthe salivinii), gray sclerotia (Ceratobasidoma) Sphaerulina ory ina), stupid seedling disease (Gibberella fujikuroi), seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spy., Rhizoctonia sp., Rhizoctonia sp. , Dictyuchus spp.), Rice leaf blight (Claviceps virens), Black-headed blight (Tilleletia barclayana), Brown rice (Curvularia spp., Alternaria spp.), Yellowing dwarf disease (Sclerothrophas disease) pv. oryzae), brown stripe disease (Acidovorax aven) e subsp. oryzae), strain rot (Erwinia chrysanthemi), yellow wilt (Phytoplasma oryzae), stripe stripe (Rice stripe tenuivirus), dwarf disease (Rice dwarf reovirus);

Wheat powdery mildew (Blumeria graminis f.sp.hordei; f.sp.tritici), rust (Puccinia strimiformis, Puccinia graminis, Pucciniarecondita leaf disease) Pyrenophora teres), Red mold disease (Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nitralis), Snow rot (Typhra incarnivalis, Typhalis mirai sialis) Scotch disease (Ustilago nuda), Namagusa smut (Tilletia caries, Tilletia controversa), Eye spot disease (Pseudocercosporella herpotrichoides), Bacterial disease (Ceratobasminidia) Blight (Phaeosphaeria nodorum), Seedling blight (Fusarium spp., Pythium spp., Rhizotonia spp., Septoria spp., Pyrenophora spp.), Bacilli (minerum) . Otrichum graminicola), ergot disease (Claviceps purpurea), leaf spot (Cochliobolus sativus), black clause disease (Pseudomonas syringae pv syringae);

Corn mold blight (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp, Phythium spp., Rhizoctonia spr.), Rust disease (Puccinia sorghihos disease, black leaves) Ustilago maydis, Colletotrichum graminicola, Northern spot disease (Cochliobolus carbonum), Brown disease (Acidovorax avenae subb. Avenis), Bacterial disease, Burr disease disease, Burr. hemi pv. zeae, wilt bacterial disease (Erwinia stewartii); grape downy mildew (Plasmopara avitolicola), rust disease (Physopella ampelopdisidi), powdery mildew (Uncinulane black and white rot) Diseases (Glomerella cingulata, Colletotrichum accutatum), black rot (Guignardia bidwelliii), vine split disease (Phomopsis vitipedra), scab (Zyophialajaisensis disease) Hermaphroditis (H licobasidium mompa), Shiromon rot (Rosellinia necatrix), crown gall temple petitioner disease (Agrobacterium vitis);

Apple powdery mildew (Podosphaera leukotricha), black spot disease (Venturia inaequalis), spotted leaf disease (Alternaria maria), red star disease (Gymnosporium yamadae), Monilia disease, spoilage disease Botryosphaeria berengeriana), Anthracnose (Colletotrichum accutatum, Glomerella cingula), Soot spot (Zyophiala jamicensis), Soot spot (Gloodesporum) sidium mompa, white leaf blight (Rosellinia necatrix), blight (Phomopsis mary, Diaporthe tanakae), brown spot (Diplocaromia terumiarumiatrum), burn injury (Erwiniaorumiarumia head disease) ), Hair root disease (Agrobacterium rhizogenes); pear black spot disease (Alternaria kikuchiana), black star disease (Venturia nashicola), red star disease (Gymnosporangia asiaticum), ring-rot disease (B. rotifera sp. Pho opsis fukushii, blight blight (Erwinia sp.), root cancer tumor (Agrobacterium tumefaciens), rust blossom blight (Erwinia chrysanthemimi pv. chrysanthemia pv. chrysanthemia peu. Pests of pear (Phytophthora cactorum, Phytophthora syringae), blight blight (Erwinia sp.); Peach black scab (Cladosporium carpophilum), homoposis rot (Phomopthos disease) Colletotrichum gloe osporioides), leaf curl disease (Taphrina deformans), perforated bacterial disease (Xhanthomonas campestris pv.). pruni), Agrobacterium tumefaciens; sweet potato anthracnose (Glomerella cinulata), larvae nuclear disease (Monilinia kusanoi), ash scab (Monilinia fracticacrum) head disease ), Resinous bacterial disease (Pseudomonas syringae pv. Syringae); oyster anthracnose (Glomerella cinulata), deciduous leaf disease (Cercospora kakii; Mycosphaerella nawae, ivy aquatic palae) s); citrus black spot disease (Diaporthe citri), green mold disease (Penicillium digitatum), blue mold disease (Penicillium italicum), common scab (Elsinophaephathophorthophorthopathia) citri), brown spot bacterial disease (Pseudomonas syringae pv. syringae), greening disease (Liberactor asiaticus), root cancer tumor (Agrobacterium tumefaciens);

Gray mold disease (Botrytis cinerea) such as tomato, cucumber, beans, strawberry, potato, cabbage, eggplant, lettuce; sclerotia disease such as tomato, cucumber, legume, strawberry, potato, rapeseed, cabbage, eggplant, lettuce, etc. (Sclerotinia sclerotiorum) ); Seedling blight of various vegetables such as tomato, cucumber, beans, radish, watermelon, eggplant, rapeseed, pepper, spinach, sugar beet (Rhizotonia spp., Phythium spp., Fusarium spp., Phytophthora spp., Sclero, etc.) ; Bacterial wilt of solanaceous plants (Ralstonia solanacearum); downy mildew of cucurbits (Pseudoperonospora) cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine blight (Didymella bryoniae), Fusarium disease (Fusarium oxysporum), plague (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici Etc.), brown spot bacterial disease (Xhanthomonas campestris pv. Cucurbitae), soft rot (Erwinia carotovora subsp. Carotovora), spotted bacterial disease Pseudomonas syringae pv. Lacrymans), Bacterial blight (Pseudomonas marginalis pv. Marginalis), Cancer disease (Streptomyces sp.), Hairy root disease (Agrobacterium cucumber) (Alternaria solani), leaf mold (Fulvia fulva), plague (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Phythium myriotylum, Phythium citrus illness) ooosporioides), scab (Clavibacter michiganensis), stem rot (Pseudomonas corrugata), black spot bacilli (Pseudomonas viridiflava), soft rot (Erwinobia s.) carotovora), leaf-knot disease (Crynebacterium sp.), dwarf disease (Phytoplasma asteris), yellow dwarf disease (Tabaco leaf curl subgroup cigeviris), eggplant powdery mildew. Phytophthora infestans, brown rot disease (Phytophthora capsici), brown spot bacterial disease (Pseudomonas citrichii), stem rot (Pseudomonas corrugata), stem rot wilt disease . Arotovora subsp carotovora), spot bacterial disease (Pseudomonas sp).;

Rapeseed black spot disease (Alternaria brassicae), black rot (Xhanthomonas campestris pv. Campestris), black spot bacterial disease (Pseudomonas syringae pav. Maculicola or black rot) Etc.), white spot disease (Cercosporella brassicae), root rot disease (Phoma lingam), root-knot disease (Plasmodiophora brassicasae), downy mildew (Peronospora parasitica), black rot (Xhanthompastrastocristocralcristocrustacto). (Pseudomonas syringae pv. Maculacola), soft rot (Erwinia carotovora) subsp. Carotovoria (Tanephophorus cumcumeris), yellow rot (Fusirum rot) dahlia); green rust (Puccinia alliii), black spot (Alternaria porri), white silkworm (Sclerotium rolfsii), white plague (Phytophthora porri), black rot (Sclerotium cedar) Curtob .. Cterium flaccumfaciens), soft rot (Erwinia carotovora subsp carotovora), spot Bacterial (Pseudomonas syringae pv syringae), rot (Erwinia rhapontici), scale rot (Burkholderia gladioli), yellows disease (Phytoplasma asteris); Garlic soft rot Disease (Erwinia carotovora subsp. Carotovora), Spring rot (Pseudomonas marginalis pv. Marginalis); Soybean purpura (Cercospora kikuchiii), Black scab (Elsinores) porthe phaseolorum), Rhizoctonia root rot (Rhizoctonia solani), stems late blight (Phytophthora sojae), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthracnose (Colletotrichum truncatum, etc.), leaf grilled disease (Xhanthomonas campestris pv . Lycines), spotted bacterial disease (Pseudomonas syringae pv. Glycinea);

Kidney anthracnose (Colletotrichum lindemuthianum), bacterial wilt (Ralstonia solanacearum), bacterial wilt (Pseudomonas syringaee pv. Black astringent disease (Mycosphaerella berkeleyi), brown spot disease (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); pea powdery mildew (Erysiphe pisi), downy mildew (Peronisporum) (Pseudomonas syringae pv. Pisi), vine rot fungus (Xhanthomonas campestris pv. Pisi); cucumeris, plague (Phytophthora infestans), silver scab (Helminthosporum solani), dry rot (Fusarium oxysporum, Fusarium solani), powdery scab (Spongosporasora teresa) anacearum), black foot disease (Erwinia carotovora subsp. atroseptica), scab (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. carotovora), viscous rot (Crostridium spp.), Wakusabyo (Clavibacter michiganensis subsp. sepedonicus); sweet potato blight (Streptomyces ipomoea); sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachtii), black root disease (Aphanomyces) ioides), snake eye disease (Phoma betae), root cancer tumor (Agrobacterium tumefaciens), scab (Streptomyces scabies), spot bacterial disease (Pseudomonas syringae pv. Aptta);

Carrot black leaf blight (Alternaria dauci), knot disease (Rhizobacter dauci), root cancer disease (Agrobacterium tumefaciens), Streptomyces orporosis, roinva spr. Strawberry powdery mildew (Sphaerotheca aphanis var. Aphanis), plague (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot (Pythium ultimatum), and bacterial rot (Xanthomas) c mpestris), Bacterial Blight (Pseudomonas marginalis pv. marginalis); Chamodium wilt (Exobasidium reticulatum), white rot (Elsinois leucospira), anthracnose (Colletostris rot) Burning disease (Pseudomonas syringae pv. Theae), bitter sickness (Xhanthomonas campestris pv. Theicola), crow's nest disease (Pseudomonas sp.); Erumum, anthrax (Colletotrichum gloeosporioides), plague (Phytophthora nicotianae), wildfire (Pseudomonas syringaeepuvaetabialum), yellowseed bacteria disease (Pseudomonaseusoleisellae disease). Blight (Ralstonia solanacerum), tobacco mosaic virus (Tobaco mosaic virus); Cotton wilt (Fusarium oxysporum); Sunflower mycorrhizal disease (Sclerotinia sclerotiorum), Hornpoint disease (Xhanthonoma) stris pv. malvacearum), cavernous disease Erwinia carotovora subsp. carotovora), spotted bacterial disease (Pseudomonas syringae pv. helicanthi); Scab (Agrobacterium tumefaciens); Brown leaf spot of chrysanthemum (Septoria obesa), White rust (Puccinia horiana), Phytophthora tocrobocrum (Pseudorotoruscosis) ra), root cancer tumor (Agrobacterium tumefaciens), hair root disease (Agrobacterium rhizogenes), greening disease (Phytoplasma aurantifolia disease), turf brown patch disease (Rhizoctonia solapolia disease) (Curvularia sp.), Rust (Puccinia zoysiae), Helmintosporium leaf blight (Cochliobolus sp.), Cloud disease (Rhynchosporium secalis), Blight (Gaeumnomyces gramriscori) spp. Tan Nuclear disease (Typhula incarnata), Snow rot black granule nuclei (Typhula ishikariiensis), Snow rot large particle nuclei (Myriosclerotinia borealis), Fairy ring disease (Marasmius oreides, etc.), Phium disease (Pyum disease, etc.) Pyricularia grisea) and the like.

Secondly, a herbicidal composition with reduced phytotoxicity comprising a safener and a herbicidal compound will be described.

The above-mentioned safener agent is used as the safener included in the “herbicide-reduced herbicidal composition comprising a safener and herbicidal compound” (hereinafter referred to as herbicidal composition) of the present invention. it can.

Examples of the herbicidal compound contained in the herbicidal composition of the present invention include, in addition to herbicidal compounds selected from the group consisting of the following (A1) to (A6) or salts thereof, for example, bromobutide, cimethrin, dimetamethrin, bentazone. , Daimlon, Cumyluron, Oxadichromene, Esprocarb, Pyributicarb, Molinate, Synmethylin and the like.

From the viewpoint of the effect of the present invention, the herbicidal composition of the present invention is preferably at least one herbicidal compound selected from the group consisting of the following (A1) to (A6) or a salt thereof, More preferably, it is at least one herbicidal compound selected from the group consisting of the following (A2) and (A3) or a salt thereof.
(A1) ACCase-inhibiting herbicidal compound (A2) acetolactate synthase-inhibiting herbicidal compound (A3) whitening-type herbicidal compound (A4) VLCFA-inhibiting herbicidal compound (A5) protopolyfilinogen IX oxidase-inhibiting herbicidal compound Compound (A6) synthetic auxin herbicidal compound

The (A2) is preferably (A2-1) a sulfonylurea herbicidal compound, a pyrimidinylsalicylic acid herbicidal compound or a triazolopyrimidine herbicidal compound, and the (A3) is (A3-1) a pyrazole herbicidal compound Or triketone herbicidal compounds are preferred.

In the present invention, at least one herbicidal compound selected from the group consisting of (A2-1) and (A3-1) or a salt thereof is more preferable.

The herbicidal composition of the present invention can contain the carrier and the adjuvants exemplified in the phytotoxicity reducing agent in addition to these herbicidal compounds.

The content of the herbicidal compound in the composition of the present invention is usually in the range of 0.1 to 90% by weight, preferably in the range of 1 to 80%, and more preferably in the range of 5 to 50. % Range.
The total content of the safener and the herbicidal compound in the composition of the present invention is usually in the range of 0.1 to 90% by weight, preferably in the range of 1 to 80%, Preferably, it is in the range of 5 to 50%.

The mixing ratio of the safener and the herbicidal compound in the composition of the present invention is usually a ratio of 0.001 to 1000 of the safener with respect to the herbicidal compound by weight, preferably 0.01 to 1,000. A ratio of 100.

The herbicidal composition of the present invention can be produced according to a conventional method relating to the production of general agricultural chemicals. At least two kinds of active ingredients, a bactericidal compound and a herbicidal compound, which are active ingredients of a safener, are mixed, and if necessary, the above-mentioned carrier, the above-mentioned auxiliary agent, etc. are mixed as necessary. A composition containing either a fungicidal compound or a herbicidal compound that is an active ingredient of a safener or the herbicidal compound, and then adding the other to the composition. A herbicidal composition with reduced phytotoxicity containing both active ingredients may be produced.

Usually, preferably a mixture in which both active ingredients are mixed is prepared to produce the herbicidal composition with reduced phytotoxicity.
The herbicidal composition of the present invention can be formulated into dosage forms such as wettable powders, flowable powders, granular wettable powders, OD drugs, powders, liquids, emulsions, granules, and packs.

From the viewpoint of the effects of the present invention, the herbicidal composition of the present invention is such that the active ingredient contained in the safener is at least one selected from the group consisting of hydroxyisoxazole, picalbutrazox and amisulbrom. The compound or a salt thereof, and the herbicidal compound is preferably at least one compound selected from the group consisting of (A1) to (A6) or a salt thereof.

The herbicidal composition of the present invention has bactericidal activity and can also be used as weed control due to the original herbicidal activity. Weeds that can be controlled include, for example, barb, bean bark, enokirogusa, akinoenokorogusa, kienokorokusa, inubibies, okisakiki, texas panicum, melicennium millet, seiban sorghum, shutter cane, gypsywheat, oats, blackgrass, blackgrass, blackgrass Canary Creek Saeyoshi, Alaska Plover, Vulgaris, Shibumugi, Kogomegatsutsu, Hamasuge, Kihamasuge, Surihiyu, Blue-headed Oyster, Hagaga Ogatetou, Ichibibi, American King Deer, Buckwheat , Inuta, Inu Dazuki, White-bellied morning glory, Malba morning glory, American morning glory, Ma North American morning glory, Bean morning glory, Atlantic convolvulus, Giant scorpionfish, Photonosa, Onamomi, Wild sunflower, Dog chamomile, Chamomile, Corn marigold, Oroshagiku, Ragweed, Oobakusa, Himemukashimugi, Mugwort, Sawlet moth White clover, kuzu, raven, cypress, bumblebee, yamgra, chickweed, wild radish, black-bellied pear, prunus, blue-billed puffer, freckled grass, field pansy, wild pansy, daisies, forget-me-nots, giant white-headed scots , Field weeds such as horsetail, Tainubie, Himetariinubie, Tamagayatsuri, Kogomega Tsuri, Hiderico, Matsubai, Inuhotarui, Taiwan Yamai, Mizugayatsuri, Kurowai, Koukiyagara, Shizui, Konagi, Azena, Abnome, Kikashigusa, Himeisohagi, Mizohakobe, Chuteidae, Urikawa, Heramoda, Omodahaze But not limited to, paddy field weeds such as, but not limited to, Ibokusa, Kishuusuzumenohie, Ezonosayanucagusa, Taketoazena, Giant Abnome, Hosobahimemesohagi, Taukogi, American Sendangsa, Kusanem, American Tsunosanem, Azegaya, Algae, etc.

Since the herbicidal composition of the present invention contains the phytotoxicity reducing agent of the present invention, avoiding phytotoxicity to crops caused by the herbicidal compound, for example, growth inhibition, appearance of brown spots, yellowing, withering, wilt etc. Is possible.
Examples of target crops include crops exemplified in the safeners.

Third, a method for reducing phytotoxicity to crops using the phytotoxicity reducing agent of the present invention or the herbicidal composition of the present invention will be described.

In the present invention, phytotoxicity to crops can be reduced by an application method selected from the group consisting of the following (B1) to (B4).
(B1) The phytotoxicity reducing agent of the present invention (hereinafter referred to as phytotoxicity reducing agent a) and the herbicidal composition not containing phytotoxicity reducing agent a (hereinafter referred to as herbicidal composition b) are mixed and applied. Method,
(B2) a method of independently applying the safener agent a and the herbicidal composition b to the same crop,
(B3) a method of applying the safener a and the herbicidal composition of the present invention (hereinafter referred to as herbicidal composition c) independently to the same crop,
(B4) A method of applying the herbicidal composition c.

As the herbicidal composition b, the same herbicidal composition of the present invention can be used except that it does not contain a safener.
In the present invention, the safener a is hydroxyisoxazole, picalbutrazox, amisulbrom or a salt thereof, and the herbicidal composition b is selected from the group consisting of the above (A2-1) and (A3-1) And at least one herbicidal compound or a salt thereof.

In the present invention, the application method selected from the group consisting of (B1) to (B4) is performed once or twice on the plant body before transplanting, or on the soil and / or the root or rhizome of the plant body. Can be performed once or twice.
In the application method of (B2), the safener agent a is applied once or twice to the plant body before transplanting, and the herbicidal composition b not containing the safener agent is transplanted into the soil and / or the plant body. It is preferable that the crop is rice.

In these application methods, the safener a, the herbicidal composition b or the herbicidal composition c is treated to the plant body and / or seed, or applied to the soil and / or the root or rhizome of the plant body. To process. Below, the application method of said (B1) thru | or (B4) is demonstrated in detail.

Examples of the method for applying the safener agent a, the herbicidal composition b or the herbicidal composition c in the above (B1) to (B4) include, for example, foliage spraying treatment, seedling box treatment, paddy field soil to plant individuals Treatment, application to the soil surface, soil mixing after application to the soil surface, injection into the soil, soil mixing after injection in the soil, soil irrigation, soil mixing after soil irrigation, Examples include spraying treatment on plant seeds, smearing treatment on plant seeds, dipping treatment on plant seeds, dressing treatment on plant seeds, spraying treatment on plant seeds, etc., which are usually used by those skilled in the art. Even in such application methods, it exhibits sufficient efficacy.

In the application methods (B1) to (B4), the dosage and application concentration of the safener a, the herbicidal composition b or the herbicidal composition c are the target crop, the target disease, the degree of occurrence of the disease, Although it varies depending on the dosage form, application method, various environmental conditions, etc., when spraying or irrigating, the amount of active ingredient is suitably 50 to 1,000,000 g per hectare, preferably 100 to 500 per hectare. 1,000 g. The amount used for seed treatment is 0.001 to 50 g, preferably 0.01 to 10 g, per 1 kg of seed. When the safener a, herbicidal composition b or herbicidal composition c is applied to a plant individual, foliage spraying treatment, soil surface spraying treatment, soil injection treatment, soil irrigation treatment, suitable carrier The treatment may be performed after dilution to an appropriate concentration. When contacting with plant seeds, they may be used after being diluted to an appropriate concentration and then dipped, dressed, sprayed, sprayed or smeared on plant seeds. In the case of powder coating, spraying, spraying and smearing treatment, the amount of preparation used is usually about 0.05 to 50%, more preferably 0.1 to 30% of the dry plant seed weight. The amount used is not limited to these ranges, and may vary depending on the form of the preparation and the type of plant seed to be treated.

The safener a, herbicidal composition b or herbicidal composition c may be treated alone and in combination with fungicides, insecticides, acaricides, nematicides or planting agents, simultaneously or sequentially. May be processed.

Examples of fungicides to be treated in combination include phenylamide fungicides, mitotic and mitotic inhibitors, succinate dehydrogenase inhibitors (SDHI agents), quinone external inhibitors (QoI agents), quinone internals Inhibitor (QiI killer), oxidative phosphorylation uncoupling inhibitor, quinone external stigmateline binding subsite inhibitor (QoSI agent), amino acid biosynthesis inhibitor, protein biosynthesis inhibitor, signal transduction inhibitor, lipid and cell membrane Biosynthesis inhibitors, demethylation inhibitors (DMI agents), amine fungicides, 3-ketoreductase inhibitors in C4-demethylation of sterol biosynthesis, squalene epoxidase inhibitors of sterol biosynthesis, cell wall biosynthesis Synthesis inhibitor, melanin biosynthesis inhibitor, host plant resistance inducer, dithiocarbamate fungicide, phthalimide fungicide, gua Jin fungicides, multifunctional point contact active fungicides, mention may be made of other fungicides and the like. Examples of insecticides, acaricides, and nematicides treated in combination include carbamate acetylcholinesterase (AChE) inhibitors, organophosphorus acetylcholinesterase (AChE) inhibitors, GABAergic chloride channel blockers , Sodium channel modulator, nicotinic acetylcholine receptor (nAChR) competitive modulator, nicotinic acetylcholine receptor (nAChR) allosteric modulator, glutamatergic chloride channel (GluCl) allosteric modulator, juvenile hormone analog, non-specific ( Multisite) inhibitors, mite growth inhibitors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers that disrupt proton gradients, nicotinic acetylcholine receptors (n ChR) channel blocker, chitin biosynthesis inhibitor type 0, chitin biosynthesis inhibitor type 1, fly insect molting inhibitor, molting hormone (ecdysone) receptor agonist, mitochondrial electron transport complex III inhibitor, mitochondrial electron transfer Complex I inhibitor (METI), voltage-gated sodium channel blocker, acetyl CoA carboxylase inhibitor, mitochondrial electron transport complex IV inhibitor, mitochondrial electron transport complex II inhibitor, ryanodine receptor modulator, stringed organ Modulator Target site unspecified, other agents, and the like can be used, and one or more can be used in combination, but are not limited thereto.

Examples of fungicides include, for example, benalaxyl, benalaxyl M or chiralaxyl (benalaxyl-M or kiralaxyl), furalaxyl, metalaxyl (x), metalaxyl (x), or mephenoxam (x). , Phenylamide fungicides such as ofurase;
Carbendazim (carbendazim), fuberidazole (fuberidazole), thiabendazole (thiabendazole), thiophanate (thiophanate), diethofencarb (diethofencarb), zoxamide (zoxamide), ethaboxam (ethaboxam), pencycuron (pencycuron), fluopicolide (fluopicolide), Fenamakuriru (phenamacril) Mitotic and mitotic inhibitors such as;
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flupyranf, fluxilaf ), Furametopyr, isofetamide, isopyrazam, mepronil, oxycarboxin, penthiopyrad, flufluto n), sedaxane, thifluzamide, pyraziflumid, isoflupyram, fluindapyr, inpyrflupromopine, inpyrflupromopine Agent (SDHI agent);
Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenamidone, fenamine Phenoxystrobin, fluoxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, oryastrostrobin (orysastrobine) icoxystrobin, pyraclostrobin, pyramethostrobin, pyraoxystrobin, pyribencarb, triclopyrytyl, tricropyribine, tritropyrbin ) External quinone inhibitors (QoI agents):
Oxidative phosphorylation uncoupling inhibitors such as binapacryl, meptyldinocap, dinocap, fluazinam;
A quinone external stigmaterin binding subsite inhibitor (QoSI agent) such as amethoctradin;
Amino acid biosynthesis inhibitors such as cyprodinil, mepanipyrim, pyrimethanil;
Protein biosynthesis inhibitors such as streptomycin, blastcidin-S, oxytetracycline;
Fenpiclonil, fludioxonil, quinoxyphene, proquinazide, clozolinate, dimethaclone, iprodione, iprodione, iprodione, iprodione ;
Edifenphos, iprobenfos, pyrazophos, biphenyl,
Chloroneb, dichloran, quintozene, technazene, tolclofos-methyl, etiodiazole (ecloromol), iodocarbo, p Lipid and cell membrane biosynthesis inhibitors;
Azaconazole, bittertanol, bromuconazole, cyproconazole, difenoconazole, dinicoconazole, dinicoconazole, dinicoconazole, dinicoconazole, dinicoconazole. Conazole (epoxiconazole), etaconazole, fenarimol, fenbuconazole, fluquinconazole, fluconconole, fluconconole, fluconazole, fluconazole Hall (flutia fol), hexaconazole (hexazolole), imidazole (imazoleol), imiconazole (mol) ), Oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconol , Pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconiole, triaditrifone, triazidifonol Demethylation inhibitors (DMI agents) such as (trifoline), triticonazole, mefentrifluconazole, ipfentrifluconazole, etc .;
Aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine (spiroxamine), etc.
3-keto reductase inhibitors in C4-demethylation of sterol biosynthesis such as fenhexamide, fenpyrazamine;
Squalene epoxidase inhibitors of sterol biosynthesis, such as piributicalb, [b-15.2] naphthifine, [b-15.3] terbinafine;
Polyoxins, dimethomorph, dimorphorph, pyrimorph, benthiavalicrub, benchavalipropyl Cell wall biosynthesis inhibitors such as varifenate;
Phthalide or fthalide, pyroquilon, tricyclazole, carpropamide, diclocymet, phenoxanil, olprocarbin, olprocarbin, olprocarbin
Host plant resistance inducers such as acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, laminarin, dicloventiazox, etc .;
Mancozeb, manzeb or manzeb, manneb, methiram, propineb, thiuram, zineb, ziram, felbamate, etc. ;
Captan, captafol, holpet, fluorophorpet, etc .;
Phthalimide fungicide:
Guanidine fungicides such as guazatine, iminoctadin, iminoctaine albecylate, iminoctaine triacetate;
Basic copper chloride, cupric hydroxide (copper (II) hydroxide), basic copper sulfate, organic copper compound (organocopper compound), bisethylenediamine copper complex salt of dodecylbenzenesulfonate ] (Dodecyl benzene sulphonic acid bisethylene diamine copper [II] salt, DBEDC), sulfur, fluorimide, dicyclofluanid, dilfluanide, diluluanide Multi-acting point contact active fungicides such as onato (chinomesionat or quinomethionate), extract from cotyledons of lumberjack seedlings (BLAD);
Dicloventiazox, fenpicoxamide, dipymethitrone, bupirimate, dimethylirimol, dimethylirimol, triphenyltinate, intritritinate acetate fentin chloride, triphenyltin hydroxide, oxolinic acid, hymexazole, octylinone, fosetyl, phosphorous acid, phosphorous acid salt (Sodiu phosphite, ammonium phosphite, potassium phosphite, teclophthalam, triazolide, trisulfide, flusulfide flusulfide, flusulfide flusulfide Diflumetrim, metasulfocarb, cyflufenamide, metraphenone, priofenone, dodine, [fluthianil, flutiilil mzone), oxathiapiproline, tebufloquin, validamycins, cymoxanil, quinofumelin, fenpicominamide (fenpicominamide) Other fungicides such as (pyridachlomethyl), ipflufenoquin, fluopimimide, florylpicoxamide, and the like.

Insecticides include phosphocarb, aranicarb, butocarboxim, butoxycarboxim, thiodicarb, thiophanodib, thiophanodib, thiophanodix, , Benfuracarb, carbaryl, carbofuran, carbosulfan, etiofencarb, fenobucarb, formethanate, formetanate b), isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxyur, trimetacarb, trimetacarb, trimetacarb, trimetacarb, trimetacarb, trimetacarb allylcarb, aldoxycarb, bufencarb, butacarb, carbanolate, metocarb, xylylcarb, xylylcarb, xylylcarb, xylylcarb, xylylcarb b), carbamates acetylcholinesterase such as bendiocarb (bendiocarb) (AChE) inhibitor;
Acephate, azamethiphos, azinephos-methyl, azinephos-ethyl, ethephone, cadusafos, chloroethoxyphos, chloroethoxyphos chlorfenvinphos), chlormefos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demethon-S-methyl-demethon-S-methyl (demethon) The Difenfothion, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, O-ethyl O-4-nitrophenyl phenylphosphonothiol O-4-nitrophenyl phenylphosphothioate, etion, ethophos, femfur, fenamifos, fenitrothion, fenthion, fenthito Heptenophos, isofenphos-methyl, isocarbophos, isoxathion, malathion, mecarbamine, methamidhothium, methamidometh Tocrofos, nared, ometoate, oxydemethon-methyl, parathions, parathion-methyl, phentoate e), forate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenophos, propetrofos, ropetrophos ), Pyraclofos, pyridafenthion, quinalphos, sulfotep, tebupyrimfos, temephos, tebufos, tebufos, tebufos, tebufos iazophos, trichlorfon, vamidion, chlorthion, bromfenvinfos, bromphos, bromphos, ethylphosphine, thiophos, ethyl. ), Chlorphoxim, Sulprofos, Diamidafos, Tetrachlorvinphos, Propaphos, Mesulfenfos, Dioxabenzofos (dioxen) offos), etrimfos, oxydeprofos, formothion, fensulfothion, isazofos, imiciafos, osamifoth, osamifos Organic phosphorus acetylcholinesterase (AChE) inhibitors;
GABAergic chloride ion blockers such as chlordane, endosulfan, lindane, dienochlor, etiprole, fipronil, and acetoprole;
Acrinathrin, Allethrin [(1R) -isomer] (Allethrin [(1R) -isomer]), Bifenthrin, Bioallethrin, Bioarethrin S-Cyclopentenyl isomer (bioS) Bioresmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothin-cylathrin thrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, beta-cypermethrin, zeta-cypermethrin (zeta-permethrin). Phenothrin [(1R) -trans-isomer] (cyphenothrin [(1R) -trans-isomer]), deltamethrin (deltamethrin), empentrin [(EZ)-(1R) -isomer] (empentrin [(EZ)-(1R) -Isomer]), esfenvalerate, etofenprox (ethofenprox) rox), fenpropatrin, fenvalerate, flucitrate, flumethrinate, flumethrin, tau-fluvalinate, halfenproxin, iproprothrin Methotrin, methfluthrin, epsilon-methfluthrin, monfluorothrin, epsilon-monfluthrin, persil-methrintrin, persilin [(1R) -trans-isomer] (phenothrin [(1R) -trans-isomer]), praretrin, resmethrin, cadethrin, silafluofen, tefluthrin (f) tetramethrin), tetramethrin [(1R) -isomer] (tetramethrin [(1R) -isomer]), tralomethrin, transfluthrin, ZXI8901 (3- (4-bromophenoxy) phenyl difluoromethod) -α- (1- methylethyl) benzeneacetate), biopermethrin, furamethrin, profluthrin, flurothrinate, flurothrinate, dimethurthrin, dimethurthrin. sodium channel modulators such as phenothrin, fluvalinate;
Acetamiprid, clothianidin, dinotefuran, imidacloprid, itenocropride, ti, thimethoxam, thimethoxam ), Nicotinic acetylcholine receptor (nAChR) competitive modulators such as flupiradifurone, triflumezopyrim;
Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as spinosad, spinetoram;
Glutamatergic chloride channel (GluCl) allosteric modulators such as abamectin, emamectin benzoate, lepimectin, milbemectin;
Juvenile hormone analogs such as hydroprene, kinoprene, methoprene, phenoxycarb, pyriproxyfen, etc .;
Methyl bromide, chloropicrin, cryolite, sulfuryl fluoride, borax, boric acid, disodium octaborate, disodium octoate Non-specific (multisite) inhibitors such as sodium metaborate tartaretic, dazomet, metham, metham sodium, etc .;
Chordal organ TRPV channel modulators such as pymetrozine, pyrifluquinazone;
Mite growth inhibitors such as clofentezine, diflovidazin, hexythiazox, etoxazole;
Mitochondrial ATP synthase inhibitors such as diafenthiuron, azocyclotin, cyhexatin, phenbutatin oxide, propargite, tetradiphone, etc .;
Oxidative phosphorylation uncouplers that disrupt proton gradients, such as chlorfenapyl, DNOC (dino-ortho-cresol), binapacryl, sulfuramide;
Nicotinic acetylcholine receptor (nAChR) channel blockers such as bensultap, cartap hydrochloride, thiocyclam, monosultap;
Bistrifluron, chlorfluazuuron, diflubenzuron, flucycloxuron, flufenoxuron, hexafluururon, hexafluururon ), Nobiflumuron, teflubenzuron, triflumuron and other chitin biosynthesis inhibitors type 0;
Chitin biosynthesis inhibitor type 1 such as buprofezin;
Fly insect insect molting inhibitors such as cyromazine;
Molting hormone (ecdysone) receptor agonists such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide, etc .;
Octopamine receptor agonists such as amitraz;
Mitochondrial electron transport complex III inhibitors such as hydramethylnon, acequinocyl, fluacrylpyrim, bifenazate;
Fenazaquin, fenpyroximate, pyridaben, pyrimidifene, tebufenpyrad, tolfenpyrad, ME mitochondria e
Voltage-gated sodium channel blockers such as indoxacarb, metaflumizone;
Acetyl CoA carboxylase inhibitors such as spirodiclofen, spiromesifen, spirotetramat;
Aluminum phosphide, calcium phosphide, hydrogen phosphine, zinc phosphide, calcium cyanide, sodium cyanide (potassium cyanide), potassium cyanide (potassium cyanide), potassium cyanide (potassium cyanide), potassium cyanide (potassium cyanide) mitide mitochondrial electron transport complex IV inhibitor;
Mitochondrial electron transport system complex II inhibitors such as cenopyrafen, cyflumethofen, piflubumide;
Ryanodine receptor modulators such as chlorantaniprole, [c cyantraniliprole, fulbendamide];
Chord sound modulator such as flonicamid Target site unspecified;
Azadirachtin, benzoximate, phenisobromolate, quinomethionate, dicofol, pyridalyl, bromopropirate, bromopropilazyl ), Dinobuton, dinocap, hydrogen cyanide, methyl iodide, caranjin, mercuric chloride, methyl isothiocyanate is thiocynate, pentachlorophenol, phosphine, piperonyl butoxide, polyactin complex, sabadilla, sulcobul, sodium sulcoulone ), Aldrin, amidithione, amidothioate, aminocarb, amiton, aramite,] athithion, azotoate, azopolyate Barium polysulfide, benclothiaz, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone (5- (1,3-benzodioxole-5) -Yl) -3-hexylcyclohexa-2-enone), 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (1,1-bis (4-chlorophenyl) -2-ethylethanol, butonate), Butopyronoxyl, 2- (2-butoxyethoxy) ethyl thiocyanate (2- (2-butoxyethoxy) ethyl thiocyanate), camphechlor lor), chlorbenside, chlordecone, chlordiform, chlorfenethol, chlorfenson, fluorazol, fluoramilone (Levamisol), amidoflumet, pyrafluprole, pyriprole, tralopyril, flupirazofos, difenenolate, orophenolate. benzilate, flufenzine, benzomate, flufenerim, albendazole, oxybendazole, fenbendazole, etam-sodium, metam sodium -Dichloropropene, flometoquin, cyclaniprole, tetraniliprole, brofuranilide, dichloromezothiaziozirozide ene dibromide, acrylonitrile, bis (2-chloroethyl) ether (bis (2-chloroethyl) ether), 1-bromo-2-chloroethane, 3-bromo-1-chloroprop -1-ene (3-bromo-1-chloro), bromocyclen, carbon disulfide, carbon tetrachloride, nemadectin, cymamipolysulfide (cymazole polysulfide) calcium polysulfide), cytokinin, 2- (oct Lucio) ethanol, potassium oleate, sodium oleate, machine oil, tar oil, anabasine, morantel tartarate, insecticide (Pyrethrum), rapeseed oil, soybean reticin, starch, hydroxypropyl starch, fatty acid glyceryl ester, propyl monoglyceryl ester ester), diatomite. Afoxolaner, fluazaindolizine, aphidopyropene, cyhalodiamide, thioxafenel, fluhexaflurane Roll (tetrachloranlaniprole), saloraner (sarolaner), rotilaner (rotilaner), cycloxapride, fluenesulfone (fluensulfone), TPIC (tripropropyl isocyanurate), D-D (1,3-Dichloropropene), peroxocarbonate, MB-599 (verbutin), bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl)) ether), DCIP (bis (2-chloro-1-methylethyl) ether), ENT-8184 (N- (2-Ethylhexyl) bicyclohept-5-ene-2,3-dicarboximide), Bayer 22408 (O, O-diethyl) O-naphthalimido phosphorothioate), Bayer 32394 (tris (1-dodecyl-3-methyl-2-phenyl) enzimidazolium) hexacynoferrate), benzpyrimoxan, acynonapyr, flupyrimin, icyclopirosulfone, oxazospirol, p It is done.

The following shows formulation examples, test examples, and application examples of a phytotoxicity-reducing agent comprising the bactericidal compound of the present invention as an active ingredient, and a phytotoxicity-reduced herbicidal composition comprising the phytotoxicity-reducing agent and a herbicidal compound, The present invention will be specifically described, but the present invention is not limited thereto.

In addition, all the compounding parts of each component described in the following formulation examples mean parts by weight.

<Reference Example 1 (Synthesis of Pical Butrazozox)>
In accordance with the method described in Production Example 24 of Patent Document 6,
(1-Methyl-1H-5-tetrazolyl) -phenyl-methanone oxime 3.46 g and t-butyl benzoyl- (6- (bromomethyl) pyridin-2-yl) carbamate [CAS No. 1334119-10-6] t-butyl benzoyl- {6-((Z)-(1-methyl-1H-5-tetrazolyl) phenylmethylene-aminooxymethyl) -2-pyridyl which is a synthetic intermediate from 13.69 g } After 2.47 g of carbamate was obtained, it was reacted with 20% NaOH aqueous solution in a methanol solvent to obtain 1.68 g of picarbutrazox.
¹ H-NMR (CDCl ₃ ) δ: 7.86 (1H, d, J = 8.3 Hz), 7.65 (1H, t, J = 8.0 Hz), 7.51 (2H, t, J = 4.3 Hz), 7.44 (1H, dd, J = 8.4, 6.3 Hz), 7.38 (2H, t, J = 7.5 Hz), 7.22 (1H, s), 6.93 (1H, d, J = 7.3 Hz), 5.25 (2H, s), 3.98 (3H, s), 1.52 (9H, s).

<Formulation Example 1 (Picbutrazox wettable powder)>
Picalbutrazox: 10 parts, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite (registered trademark) : 0.8 part, H fine powder: the balance, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 2 (hydroxyisoxazole / pyrimisulphan wettable powder)>
Hydroxyisoxazole: 30 parts, Pyrimisulphan: 2 parts, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part , Radiolite: 0.8 part, H fine powder: remainder, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 3 (Amisulbrom / Imazosulfuron wettable powder)>
Amisulbrom: 20 parts, Imazosulfuron: 1 part, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite (registered) Trademark): 0.8 parts, H fine powder: the balance, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 4 (Chiazofamide / Imazosulfuron wettable powder)>
Cyazofamid: 10 parts, Imazosulfuron: 0.5 part, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite (Registered trademark): 0.8 parts, H fine powder: remainder, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 5 (Kasugamycin pyrazolate wettable powder)>
Kasugamycin: 1 part, Pyrazolate: 50 parts, Neogen powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite (registered) Trademark): 0.8 parts, H fine powder: the balance, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 6 (Chlorothalonyl sulcotrione wettable powder)>
Chlorotalonyl: 30 parts, Sulcotrione: 10 parts, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite ( (Registered trademark): 0.8 parts, H fine powder: remainder, 100 parts in total were ground and mixed to obtain a wettable powder.

<Formulation example 7 (benomyl tenyl chlor wettable powder)>
Benomyl: 20 parts, Tenilchlor: 5 parts: 50 parts, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radio Light (registered trademark): 0.8 part, H fine powder: remaining part, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 8 (Thiophanate methyl pyrimisulfane wettable powder)>
Methyl thiophanate: 40 parts, Pyrimisulphan: 3 parts, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part, Radiolite (Registered trademark): 0.8 parts, H fine powder: remainder, 100 parts in total were pulverized and mixed to obtain a wettable powder.

<Formulation Example 9 (Picalbutrazox / pyrimisulphan wettable powder)>
Pical butrazoz: 10 parts, Pyrimisulphan: 1 part, Neogen Powder (registered trademark): 0.5 part, Carplex (registered trademark): 0.5 part, Gohsenol (registered trademark): 0.2 part Radiolite (registered trademark): 0.8 part, H fine powder: remaining part, and a total of 100 parts were ground and mixed to obtain a wettable powder.

<Formulation Example 10 (Pical Butrazozus / Pyrimisulphan Granules)>
Picalbutrazox: 3 parts, Pyrimisulphan: 0.3 part, 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of CMC sodium, 64.5 parts of clay, 27.7 parts of talc After uniformly pulverizing and mixing, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 11 (hydroxyisoxazole / pyrimisulphan granule)>
Hydroxyisoxazole: 5 parts, Pyrimisulphan: 0.2 parts, 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of CMC sodium, 62.6 parts of clay, 27.7 parts of talc After uniformly pulverizing and mixing, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 12 (Amisulbrom / Imazosulfuron Granules)>
Amisulbrom: 5 parts, imazosulfuron: 0.4 parts, polyoxyethylene / polyoxypropylene condensate 1.5 parts, CMC sodium 3 parts, clay 56.4 parts, talc 33.7 parts, after uniformly mixing Then, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 13 (Chiazofamide / Imazosulfuron Granules)>
Cyazofamid: 2.5 parts, Imazosulfuron: 0.2 parts, 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of CMC sodium, 59.1 parts of clay, 33.7 parts of talc After mixing, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 14 (Kasugamycin / Pyrazolate Granules)>
Kasugamycin: 0.1 parts, pyrazolate: 20 parts, polyoxyethylene / polyoxypropylene condensate 1.5 parts, CMC sodium 3 parts, clay 53.7 parts, talc 21.7 parts, after uniformly grinding and mixing Then, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 15 (Chlorothalonyl sulcotrione granules)>
Chlorotalonyl: 4 parts, Sulcotrione: 1 part, Polyoxyethylene / polyoxypropylene condensate 1.5 parts, CMC sodium 3 parts, clay 65.8 parts, talc 33.7 parts Water was added and kneaded and granulated and dried to obtain granules.

<Formulation example 16 (benomyl tenyl chlor granules)>
Benomyl: 5 parts, Tenylchlor: 1 part, 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of CMC sodium, 68.8 parts of clay, 29.7 parts of talc And kneaded, granulated and dried to obtain granules.

<Formulation Example 17 (Thiophanate methyl pyrimisulfuran granules)>
Thiophanate methyl: 5 parts, pyrimisulphan: 0.4 parts, polyoxyethylene / polyoxypropylene condensate 1.5 parts, CMC sodium 3 parts, clay 62.4, talc 27.7 parts Then, water was added and kneaded and granulated and dried to obtain granules.

<Formulation Example 18 (Isoprothiolane / pyrimisulphan granule)>
Isoprothiolane: 12 parts, Pyrimisulphan: 0.4 parts, 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of CMC sodium, 55.4 parts of clay, 27.7 parts of talc, and above are uniformly ground and mixed Then, water was added and kneaded and granulated and dried to obtain granules.

Reagent (B1) Hydroxyisoxazole solution (trade name / Tatigalen (registered trademark) solution, active ingredient hydroxyisoxazole, 30% by weight, manufactured by Mitsui Chemicals Agro Co., Ltd.)
(B2) Picalbutrazox wettable powder obtained in Formulation Example 1 (B3) Amisulbrom granule wettable powder (trade name / Oracle (registered trademark) granule wettable powder, active ingredient amisulbrom, 50% by weight, Nissan Chemical Industries (Made by Co., Ltd.)
(B4) Ciazofamide wettable powder (trade name / Ranman (registered trademark) flowable, active ingredient cyazofamide, 9.4% by weight, manufactured by Ishihara Bioscience Co., Ltd.)
(B5) Kasugamycin solution (trade name / Kasmin (registered trademark) solution, active ingredient kasugamycin, 2% by weight, manufactured by Hokuko Chemical Co., Ltd.)
(B6) Chlorothalonil wettable powder (trade name / Daconil (registered trademark) 1000 wettable powder, active ingredient chlorothalonil, 40% by weight, manufactured by SDS Biotech Co., Ltd.)
(B7) Benomyl wettable powder (trade name / Benrate (registered trademark) wettable powder, active ingredient benomyl, 50% by weight, manufactured by Sumitomo Chemical Co., Ltd.)
(B8) Thiophanate methyl wettable powder (trade name / Topgin (registered trademark) M wettable powder, active ingredient thiophanate methyl, 70% by weight, manufactured by Nippon Soda Co., Ltd.)
(B9) Isoprothiolane granules (trade name / Fuji One (registered trademark) granules, active ingredient isoprothiolane, 12% by weight, manufactured by Nippon Agricultural Chemicals Co., Ltd.)
(B10) Hydroxyisoxazole powder (trade name / Tachigalen (registered trademark) powder, active ingredient hydroxyisoxazole, 4% by weight, manufactured by Mitsui Chemicals Agro Co., Ltd.)

<Test Example 1>
The chemical solutions of (B1) to (B8) are diluted to concentrations of 600 ppm, 100 ppm, 250 ppm, 94 ppm, 5000 ppm, 800 ppm, 1000 ppm, and 1000 ppm, respectively (500 times, 1000 times, 2000 times, 1000 times, 4 times, respectively) Fold, 500 times, 500 times and 700 times), irrigation of soil (B1, B2, B3, B4, B6, B7, B8; 500 ml / nursing box equivalent, B5; 50 ml / nursing box equivalent), or (B9 ) Was treated with 50 g / nursery box and (B10) was treated with 6 g / nursery box, and then a prototype (rice cultivar: Koshihikari) was sown. The seedlings (about 2.1 leaf stage) grown in a greenhouse at 26 ° C. for 17 days were again irrigated with the chemical solutions (B1) to (B8) diluted to a predetermined concentration or 50 g / (B9). After the treatment in the nursery box, the drug-treated and transplanted seedlings were obtained.

In a container (30 × 30 cm) containing paddy paddy soil, the transplanted seedlings that were not treated with drugs and transplanted were transplanted at 10 cm depth, with two at one transplantation depth of 1.5 cm. . Four days after transplantation, with a water depth of 2 cm, the pyrimylsulfur 0.66% granule (trade name / Best Partner (registered trademark) granule, manufactured by Kumiai Chemical Industry Co., Ltd.) was treated in an amount equivalent to 20 kg / ha. did. In order to eliminate the effect of weeds on paddy rice as a control, a complete weeding area where only weeds were removed was set up.
After 21 days of drug treatment, a sampling survey of the plant body was conducted.
In addition, dry weight cut into the above-ground part and a root part, and measured the weight dried at 100 degreeC for 1 hour and 80 degreeC for 2 days.
Compared with the complete weeding group, phytotoxicity was confirmed in the dry weight of the ground part and the dry part of the root part in the 0.67% granule treatment group. Regarding the group in which the phytotoxicity was confirmed, the above-mentioned sterilizer-treated group increased the above-ground dry weight and the root dry matter weight as compared with the above-mentioned sterilizer-untreated group, and it was confirmed that it had a phytotoxicity mitigating effect.

<Test Example 2>
Dilute the hydroxyisoxazole solution (B1), picalbutrazox wettable powder (B2), and amisulbrom granule wettable powder (B3) to concentrations of 600 ppm, 100 ppm and 250 ppm, respectively (500 times, 1000 times and 2000 times) Times), after irrigating the soil (500 ml / nursery box equivalent), a prototype (rice cultivar: Koshihikari) was sown. The seedlings grown in a greenhouse at 26 ° C. for 17 days (about 2.1 leaf stage) are once again diluted with the chemical solutions (B1) to (B3) diluted to a predetermined concentration, and then treated with chemicals and transplanted seedlings. It was.

In a container (30 × 30 cm) containing paddy paddy soil, the transplanted seedlings that were not treated with drugs and transplanted were transplanted at 10 cm depth, with two at one transplantation depth of 1.5 cm. . 4 days after transplantation, with a water depth of 2 cm, oxadichromephone 0.8%, tefriltrione 3% granule (trade name / A1 (registered trademark) granule, manufactured by Hokuko Chemical Co., Ltd.) equivalent to 20 kg / ha Amount processed. Moreover, 20 kg / ha equivalent amount of the pyrimyl fan 0.67% granule was processed into another container. In order to eliminate the effect of weeds on paddy rice as a control, a complete weeding area where only weeds were removed was set up.
Twenty-six days after the drug treatment, a sampling survey of the plant body was conducted.
In addition, dry weight cut into the above-ground part and a root part, and measured the weight dried at 100 degreeC for 1 hour and 80 degreeC for 2 days.

Compared with the completely weeded area, phytotoxicity was confirmed in the above-ground dry weight and root dry weight in the oxadichromephone 0.8%, tefriltrione 3% granule treated group, and the pyrimylsulfan 0.67% granule treated group. Regarding the group where the phytotoxicity was confirmed, the dry weight of the ground part and the dry part of the root part increased in the hydroxyisoxazole solution-treated group compared to the non-treated group of hydroxyisoxazole solution. confirmed.

Compared with the completely weeded area, phytotoxicity was confirmed in the above-ground dry weight and root dry weight in the oxadichromephone 0.8%, tefriltrione 3% granule treated group, and the pyrimylsulfan 0.67% granule treated group. Regarding the area where phytotoxicity was confirmed, the dry weight of the ground part and the dry part of the root part increased in the area treated with the picalbutrazox wettable powder compared with the non-treated area of the picalbutrazox wettable powder. It was confirmed to have

Compared with the completely weeded area, phytotoxicity was confirmed in the above-ground dry weight and root dry weight in the oxadichromephone 0.8%, tefriltrione 3% granule treated group, and the pyrimylsulfan 0.67% granule treated group. Regarding the area where phytotoxicity has been confirmed, the dry weight of the ground part and the dry part of the root part increased in the treated area of amisulbrom granule wettable powder compared to the untreated section of amisulbrom granule wettable powder. confirmed.

<Test Example 3>
Hydroxyisoxazole solution (B1) was diluted to give a concentration of 600 ppm (500 times) and then irrigated with seedlings (rice varieties: Sagabi) grown for 21 days (500 ml / nursery box equivalent) .

In the paddy paddy field (within Agricultural Chemistry Research Institute, Mitsui Chemicals Agro Co., Ltd., Yasu City, Shiga Prefecture), 3 treated seedlings were transplanted with 3 treated seedlings that were not treated with drugs. Five days after transplantation, 20 kg / ha equivalent amount of oxadichromephone 0.8% and tefryltrione 3% granule was treated while maintaining the water depth at 5 cm. Moreover, 20 kg / ha equivalent amount of the pyrimyl fan 0.67% granule was processed into another container. In order to eliminate the effect of weeds on paddy rice as a control, a complete weeding area where only weeds were removed was set up.
30 days after the herbicide treatment, the plant height, the number of stems, and the plant body were sampled.
In addition, dry weight cut into the above-ground part and a root part, and measured the weight dried at 100 degreeC for 1 hour and 80 degreeC for 2 days.

Compared to complete weeding plot, oxadichromemephone 0.8%, tefril trione 3% granule doubled treatment group, pyrimysulfan 0.67% granule doubled treatment group, plant height, number of stems, above-ground dry weight, root Drug damage was confirmed in dry matter weight. Regarding the group where phytotoxicity was confirmed, the number of stems, above-ground dry weight and root dry weight increased in the hydroxyisoxazole solution-treated group compared to the hydroxyisoxazole solution-untreated group. It was confirmed to have.

According to the present invention, compared with the existing safeners, the safeners can be universally used for various cultivated crops, and the safeners containing the safeners and herbicidal compounds are reduced. A herbicidal composition can be obtained.

This application claims priority based on Japanese Patent Application No. 2018-030986 filed on February 23, 2018, the entire disclosure of which is incorporated herein.

Claims (19)

1. A safener for crops comprising, as an active ingredient, at least one compound selected from the group consisting of hydroxyisoxazole, picalbutrazox, cyazofamide, kasugamycin, chlorothalonil, benomyl, thiophanate methyl, isoprothiolane and amisulbrom as an active ingredient .
2. The safener according to claim 1, wherein the active ingredient is hydroxyisoxazole, picarbutrazox, amisulbrom or a salt thereof.
3. The crops are rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugar cane, potato, grape, soybean, kidney beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, navana, Chinese cabbage, broccoli , Cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, iris, chrysanthemum, The phytotoxicity reducing agent according to any one of claims 1 and 2, which is fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
4. The phytotoxicity reducing agent according to any one of claims 1 to 3, wherein the crop is rice.
5. A herbicidal composition comprising at least one herbicidal compound or a salt thereof and a safener for a crop according to any one of claims 1 to 4.
6. The herbicidal compound is selected from the group consisting of the following (A1) to (A6), at least one herbicidal compound or a salt thereof:
   (A1) ACCase-inhibiting herbicidal compound,
   (A2) an acetolactate synthase-inhibiting herbicidal compound,
   (A3) Whitening type herbicidal compound,
   (A4) VLCFA-inhibiting herbicidal compound,
   (A5) Protopolyfilinogen IX oxidase-inhibiting herbicidal compound,
   (A6) synthetic auxin herbicidal compound,
   The herbicidal composition according to claim 5, wherein the active ingredient contained in the safener is at least one compound selected from the group consisting of hydroxyisoxazole, picarbutrazox and amisulbrom or a salt thereof. object.
7. The crop is rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, green beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, navana, Chinese cabbage, Broccoli, cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, pepper, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, raccoon, tobacco, carnation, iris, chrysanthemum The herbicidal composition according to claim 5, wherein the composition is a turf, fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
8. The herbicidal composition according to any one of claims 5 to 7, wherein the crop is rice.
9. The herbicidal property according to any one of claims 5 to 8, wherein the herbicidal compound is at least one herbicidal compound selected from the group consisting of the following (A2) and (A3) or a salt thereof. Composition.
   (A2) an acetolactate synthase-inhibiting herbicidal compound,
   (A3) Whitening type herbicidal compound.
10. The herbicidal composition according to claim 9, wherein the herbicidal compound is at least one herbicidal compound selected from the group consisting of the following (A2-1) and (A3-1) or a salt thereof.
    (A2-1) sulfonylurea herbicidal compound, pyrimidinylbenzoic acid herbicidal compound or triazolopyrimidine herbicidal compound,
    (A3-1) A pyrazole herbicidal compound or a triketone herbicidal compound.
11. A method for reducing phytotoxicity to crops by an application method selected from the group consisting of the following (B1) to (B4).
    (B1) A method of applying a mixture of the phytotoxicity reducing agent a according to any one of claims 1 to 4 and the herbicidal composition b not containing the phytotoxicity reducing agent,
    (B2) A method of independently applying the safener agent a according to any one of claims 1 to 4 and the herbicidal composition b not containing the safener agent to the same crop,
    (B3) The safener agent a according to any one of claims 1 to 4 and the herbicidal composition c according to any one of claims 5 to 10 are independently applied to the same crop. how to,
    (B4) A method of applying the herbicidal composition c according to any one of claims 5 to 10.
12. 12. The safener a, the herbicidal composition b or the herbicidal composition c is treated to plants and / or seeds, or applied to soil and / or treated to roots or rhizomes of plants. A method for reducing the phytotoxicity described in 1.
13. 13. The method for reducing phytotoxicity according to claim 12, wherein the treatment on the seed is spraying, smearing, dipping, powdering or spraying on the seed.
14. The method for reducing phytotoxicity according to claim 12, wherein the application to soil is treatment to paddy soil, treatment to the soil surface, irrigation to soil, or mixing with soil.
15. The crops are rice, wheat, barley, corn, rapeseed, cotton, sunflower, sugarcane, potato, grape, soybean, kidney beans, pea, broad bean, azuki bean, strawberry, cabbage, radish, mibuna, mizuna, turnip, navana, cabbage, blocky , Cauliflower, lettuce, non-headed lettuce, tomato, cherry tomato, eggplant, pepper, capsicum, onion, cucumber, melon, watermelon, pumpkin, spinach, sugar beet, okra, honey bee, ginger, radish, tobacco, carnation, iris, chrysanthemum, The method of reducing phytotoxicity according to claim 11, which is fig, citrus, timber (seedling), western turf (bentgrass, ryegrass, bluegrass) or Japanese turf.
16. The method for reducing phytotoxicity according to claim 11 or 15, wherein the crop is rice.
17. The application method selected from the group consisting of (B1) to (B4) is performed once or twice on the plant body before transplanting, or once or twice on the soil and / or the root or rhizome of the plant body The method of reducing the phytotoxicity of Claim 11 performed.
18. Soil and / or plant after transplanting the herbicidal composition b which does not contain the said safener agent in the application method of said (B2), applying the safener agent a once or twice to the plant body before transplanting The method for reducing phytotoxicity according to claim 11 or 17, wherein the crop is rice.
19. The safener a is hydroxyisoxazole, picalbutrazox or amisulbrom or a salt thereof, and the herbicidal composition b is selected from the group consisting of the above (A2-1) and (A3-1), at least 1 The method for reducing phytotoxicity according to claim 11, 17 or 18, which is a herbicidal compound of a kind or a salt thereof.