WO2011145318A1 - Harmful effect reduction agent for herbicide, herbicide composition having reduced harmful effect, and method for reduction of harmful effect on crops - Google Patents

Abstract

Disclosed are: a harmful effect reduction agent for a herbicide, which can reduce or suppress a harmful effect and can reduce an environmental load without requiring the use of multiple different types of herbicidally active components in combination; a herbicide composition having a reduced harmful effect; and a method for reducing a harmful effect on crops. The harmful effect reduction agent for a herbicide is characterized by containing, as the main component, a compound represented by general formula (I) (wherein R¹ represents a hydrogen atom, a hydroxyl group or a C4-C5 alkyl group; R² represents a hydrogen atom or a C4-C5 alkyl group; R³ represents a C4-C5 alkyl group; X represents a carboxyl group, an amino group, a hydroxyl group or a hydroxymethyl group; and Y represents a hydrogen atom or a hydroxyl group, wherein one of R¹ and R² represents a C4-C5 alkyl group). The herbicide composition having a reduced harmful effect is characterized by containing the harmful effect reduction agent for a herbicide and at least one specific herbicidally active compound.

Description

Herbicide safener, herbicide composition with reduced safeguard, and method for reducing crop damage

The present invention relates to a herbicide safener that can reduce or prevent phytotoxicity and reduce the environmental load without using multiple different herbicidal active ingredients in combination, herbicide composition with reduced phytotoxicity, and crop phytotoxicity. Relates to a method of reducing

Among known herbicides, for example, pyrimisulphan has a high herbicidal effect on low-dose annual perennial weeds such as Novier, Tamagayatsuri, Konagi and Himehoshihagi, and perennial weeds such as pine bay, Urikawa and Omodaka, especially paddy weeds. It is known as having a broad herbicidal spectrum (see Patent Document 1).

However, these herbicides can sometimes cause phytotoxicity to rice, especially under poor environmental conditions such as high temperatures, sandy soils, and leaked fields, and for shallow seedlings, transplants, seedlings immediately after sowing, etc. On the other hand, the phytotoxicity is further increased, and the phytotoxicity may be caused when an excessive amount is applied unintentionally or accidentally.

Therefore, conventionally, in addition to the development of herbicidal active compounds with higher selectivity, the development of herbicide safeners (Safener) for enhancing the selectivity of herbicidal active compounds has been promoted. Examples of the safeners for herbicides that have been put to practical use include fenchlorim for chloroacetanilide compounds of pretilachlor, chlorazole for phenoxaprop-ethyl of allyloxy compounds, and safeners of sulfonylurea compounds An attempt to use a benzoyloxime ether compound (see Patent Document 2) has also been proposed. However, these safeners are used only for specific herbicidally active compounds and are not widely and generally usable.

There has also been proposed an attempt to achieve both a high herbicidal effect and safety to rice by using a combination of pyrimisulphan and other specific herbicidal active compounds such as pretilachlor and butachlor (Patent Literature). 3)), however, a technology that achieves both a high herbicidal effect and safety for rice without using a plurality of herbicidal active compounds has not yet been established.

JP 2000-44546 A (Claims and others) European Patent EP-A122231 (Claims and others) JP 2000-281513 (Claims and others)

The problem of the present invention is that, under such circumstances, when the herbicidal active ingredient is simply applied, the growth of the target crops such as rice, growth inhibition, growth inhibition, phytotoxicity such as lateralization, etc. are manifested. Even if it is such, the phytotoxicity mitigation agent for herbicides that can reduce or prevent the phytotoxicity symptoms of the target crop without using multiple herbicidal active ingredients of different types and without sacrificing the herbicidal effect An object of the present invention is to provide a herbicidal composition with reduced phytotoxicity and a method for reducing phytotoxicity of crops.

As a result of extensive research to develop a herbicidal composition having the above-mentioned preferable characteristics, the present inventors have found that sulfonylurea compounds, sulfonamide compounds, chloroacetanilide compounds, which are known herbicidal active compounds, Thiocarbamate compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds, phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds, and It has been found that a herbicidal composition comprising a specific compound that does not exhibit exceptional agrochemical activity per se in an isoxazoline-based compound or a salt thereof contributes to solving the problems, and the present invention is made based on this finding. It came.

That is, the present invention provides a phytotoxicity reducing agent for herbicides as described below, a herbicide composition with reduced phytotoxicity, and a method for reducing phytotoxicity, particularly for grasses, using the herbicide.

(1) General formula (I)

(Wherein R ¹ represents a hydrogen atom, a hydroxyl group or a C4-C5 alkyl group, R ² represents a hydrogen atom or a C4-C5 alkyl group, R ³ represents a C4-C5 alkyl group, and X represents a carboxyl group. Represents an amino group, a hydroxyl group or a hydroxymethyl group, and Y represents a hydrogen atom or a hydroxyl group, wherein either R ¹ or R ² is a C4-C5 alkyl group.
A herbicide safener characterized by comprising a compound represented by

(2) The phytotoxicity reduction for herbicides according to the above (1), wherein R ¹ is a hydrogen atom or a hydroxyl group, R ² and R ³ are a C4 to C5 alkyl group, and Y is a hydrogen atom or a hydroxyl group Agent.

(3) The weeding according to (1), wherein R ¹ is a hydrogen atom, R ² and R ³ are C4 to C5 alkyl groups, X is a carboxyl group, and Y is a hydrogen atom or a hydroxyl group. Medicinal safener.

(4) R ¹ is a hydrogen atom, R ² and R ³ are C4 to C5 alkyl groups, X is an amino group or a hydroxymethyl group, and Y is a hydrogen atom. A safener for herbicides.

(5) The herbicide phytotoxicity according to the above (1), wherein R ¹ is a hydroxyl group, R ² and R ³ are C4 to C5 alkyl groups, X is a hydroxyl group, and Y is a hydrogen atom. Relief agent.

(6) The herbicide safener according to (1), wherein R ¹ and R ³ are C4 to C5 alkyl groups, R ² is a hydrogen atom, and X and Y are hydroxyl groups.

(7) The phytotoxicity reduction for herbicides according to any one of (1) to (6), wherein the C4 to C5 alkyl group is a tert-butyl group or a 1,1-dimethylpropyl group containing a quaternary carbon. Agent.

(8) (A) a safener for a herbicide according to any one of (1) to (7),
(B) sulfonylurea compounds, sulfonamide compounds, chloroacetanilide compounds, thiocarbamate compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds One or more herbicidal active compounds selected from phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds and isoxazoline compounds, or salts thereof,
A herbicidal composition with reduced phytotoxicity.

(9) The above (8), wherein the sulfonylurea compound is bensulfuron methyl, pyrazosulfuron ethyl, halosulfuron methyl, azimusulfuron, synosulfuron, cyclosulfamuron, flucetosulfuron, imazosulfuron, ethoxysulfuron, or pripyrisulfuron. A herbicidal composition with reduced phytotoxicity.

(10) The herbicidal composition with reduced phytotoxicity according to (8), wherein the sulfonamide compound is penoxsulam.

(11) The herbicidal composition with reduced phytotoxicity according to (8), wherein the chloroacetanilide compound is butachlor, pretilachlor or tenyl chlor.

(12) The herbicidal composition with reduced phytotoxicity according to (8), wherein the thiocarbamate compound is thiobencarb, esprocarb or molinate.

(13) The herbicidal composition with reduced phytotoxicity according to the above (8), wherein the pyrimidinyloxy (thio) benzoic acid compound is pyriminobacmethyl, pyriphthalide, bispyribac sodium or pyribenzoxime.

(14) The herbicidal composition with reduced phytotoxicity according to (8), wherein the tetrazolinone compound is fentolazamide.

(15) The herbicidal composition with reduced phytotoxicity according to (8), wherein the triazole-based compound is caffeentrol or ipfencarbazone.

(16) The herbicidal composition with reduced phytotoxicity according to (8), wherein the pyrazole compound is pyrazolate, pyrazoxifene, pyraclonyl or benzophenap.

(17) The herbicidal composition with reduced phytotoxicity according to (8), wherein the cyclohexanedione compound is benzobicyclone, mesotrione, or tefryltrione.

(18) The herbicidal composition with reduced phytotoxicity as described in (8) above, wherein the phenoxycarboxylic acid compound is 2,4-D, MCPA, MCPB, or chromeprop.

(19) The herbicidal composition with reduced phytotoxicity according to (8), wherein the oxazinone-based compound is oxadiclomephone.

(20) The herbicide composition with reduced phytotoxicity according to (8), wherein the difluoromethanesulfonylanilide compound is pyrimisulphan.

(21) The herbicidal composition with reduced phytotoxicity according to (8), wherein the isoxazoline-based compound is phenoxasulfone or pyroxasulfone.

(22) (A) The herbicide safener according to any one of (1) to (7), and (B) a sulfonylurea compound, a sulfonamide compound, a chloroacetanilide compound, a thiocarbamate compound Compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds, phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds and isoxazoline compounds Or a herbicidal active compound selected from the salts thereof,
A method for reducing phytotoxicity of crops caused by the herbicidal active compound, wherein the method is applied simultaneously or in proximity.

The herbicide reducing agent and herbicide composition with reduced phytotoxicity of the present invention includes a wide range of herbicidally active compounds, and when applied simply, it prevents growth disturbance, growth inhibition, and division inhibition of target crops such as rice. Even if it causes phytotoxicity symptoms such as yellowing, the phytotoxicity symptoms of the target crop can be reduced or prevented without sacrificing sufficient herbicidal effect. It is useful as a phytotoxicity reducing agent for herbicides or a herbicidal composition with reduced phytotoxicity, particularly as a phytotoxicity reducing agent or agrochemical composition for rice action or rice field rice action.

In addition, the method of the present invention can be applied to the target crop, particularly rice, even if the herbicidal active compound is applied so that phytotoxic symptoms such as growth inhibition, growth inhibition, and yellowing occur. Since it can reduce or prevent phytotoxic symptoms, it is useful as a method for reducing phytotoxicity of crops by herbicidal active compounds.

In the compound represented by the general formula (I) used as a main component in the herbicide safener of the present invention, R ¹ represents a hydrogen atom, a hydroxyl group or a C4 to C5 alkyl group, and R ² represents a hydrogen atom. Alternatively, it represents a C4 to C5 alkyl group, R ³ represents a C4 to C5 alkyl group, X represents a carboxyl group, an amino group, a hydroxyl group or a hydroxymethyl group, and Y represents a hydrogen atom or a hydroxyl group. ^One of R ¹ and R ² is a C4 to C5 alkyl group.

As the compound represented by the general formula (I), those in which R ¹ is a hydrogen atom or a hydroxyl group, R ² and R ³ are C4 to C5 alkyl groups, and Y is a hydrogen atom or a hydroxyl group are preferable. .

Of these, compounds in which R ¹ is a hydrogen atom, R ² and R ³ are C4 to C5 alkyl groups, X is a carboxyl group, and Y is a hydrogen atom or a hydroxyl group are preferred. , 5-di-tert-butylbenzoic acid and 3,5-di-tert-butyl-4-hydroxybenzoic acid.

Also preferred are compounds wherein R ¹ is a hydrogen atom, R ² and R ³ are C4-C5 alkyl groups, X is an amino group or a hydroxymethyl group, and Y is a hydrogen atom. Mention may be made of 3,5-di-tert-butylaniline and 3,5-di-tert-butylbenzyl alcohol.

Further, a compound in which R ¹ is a hydroxyl group, R ² and R ³ are C4 to C5 alkyl groups, X is a hydroxyl group, and Y is a hydrogen atom is preferable. Mention may be made of di-tert-butylcatechol.

On the other hand, as the compound represented by the general formula (I), those in which R ¹ and R ³ are C4 to C5 alkyl groups, R ² is a hydrogen atom, and X and Y are hydroxyl groups are also preferred. Specifically, 2,5-di-tert-butylhydroquinone and 2,5-di- (1,1-dimethylpropyl) hydroquinone can be mentioned.

The C4-C5 alkyl group is preferably a tert-butyl group or a 1,1-dimethylpropyl group containing a quaternary carbon. In addition, the safener for a herbicide of the present invention may be a compound represented by one or more general formulas (I) per se or a pesticide carrier described later.

In addition, the herbicidal composition with reduced phytotoxicity of the present invention,
(A) Component: A herbicide safener (B) component comprising as a main component the compound represented by the above general formula (I) component: 1 or 2 or more specific herbicidal active compounds are contained. Is.

Examples of the herbicidal active compounds of the component (B) used in combination with the component (A) include, for example, clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, diclohop-P. Methyl (dicofop-P-methyl), phenoxaprop-P-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyhop-haloxyhop (Haloxy-hop-etyl), Haloxyhop-P (haloxyhop-P), Metamihop (metamif) p), propaquizahop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-p-tefofol-p-tefofol -Ethyl), alloxydim, butroxydim, cletodim, cycloxydim, profoxidim, cetoxidim, tepraxidim (tex) ), Pinoxaden, imazametathenz-methyl, imazamox, imazapic (including salts with amines, etc.), imazapyr (i), isopropyl, ), Imazetapyr, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl salt, pyriminobac-methyl salt pyrimisulfan), fu Lucarbazone sodium salt (flucarbazone-sodium), thiencarbazone (including sodium salts, methyl esters, etc.), propoxycarbazone-sodium salt, procarbazone sodium salt (procarbazone) (Amidosulfuron), azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cinosulfuron amuron, ethamethsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupirsulfuron-urulon, ursulfuron (Halosulfuron-methyl), imazosulfuron, iodosulfuron-methyl sodium salt (iodosulfuron-methyl-sodium), mesosulfuron-methyl, metsulfuron-methyl (methsulfuron-methyl) Lonsulfuron, oxasulfuron, primisulfuron-methyl, prosulfururon-ethyl, pyrazosulfuron-methyl, rimsulfururon-methylsulfimururone , Sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron sodium salt dium), triflusulfuron-methyl, tritosulfuron, orthosulfururon, propysulfuron, metazosulfuron, metazosulfuron, metazosulfuron, metazosulfuron, metazosulfuron Methyl (cloransulam-methyi), dicloslam (florasuram), flumetsulam (flumetsulam), metosulam (penoxsuram), penoxslam (penoxsulm (PC), N-90) Number), desmedifam, phenmedifam, chloridazon, brompyrazone, ametrin, atrazine, esandetamine, neandetaminedine (Dimethametrin), eglinazine-ethyl, promethon, promethrin, propazine, simazine, bimetriter, termethyton Terbutrin, trietazine, metamitron, metribuzine, amicarbazone, bromacil, renail, pentyl, lenpacil ), Chlorbromuron, chlorotoluron, chloroxuron, dimeflon, diuron, etidimuron, fenuron, fluometuron (flumeturon) on), isoproturon (isoproturon), isouron (isoouron), linuron (linuron), metabenzthiazuron (methabenzthiauron), methobromuron (metoxuron) (metoxuron), monolinuron (uronururon) ), Tebuthiuron, Metobenzuron, Bentazone, Bromofenoxim, Bromoxynil (including esters such as butyric acid, octanoic acid or heptanoic acid), ioxyn, ioxyn (Pyr dafol, pyridate, diquat, paraquat dichloride, acifluorfen-sodium, bifenox, clomethoxyphene, thoxyf e-th Fen (fluoroglycen-ethyl), fomesafen, lactofen, oxyfluorfen, cinidon-ethyl, flumicrolac-pentoxine (flulochlor-pentoxine) Chlorphthalim, oxadiaargyl, oxadiazon, pentoxazone, fluazolate, pyraflufen-ethyl, benzzene. ), Fluthiacet-methyl, thidiazimin, azaphenidin, carfentrazone-ethyl, sulfentrazone. , Bencarbazone, norflurazon, diflufenican, picolinaphene, benzobicyclon, isototriole, xylose, folasulfitol Chloritol, benzofenap, pyrazolate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, tembotrione Pyrasulfotole, topramezone, bicyclopyrone, 4-chloro-5- (1,3-dioxocyclohex-2-yl) carbonyl-2,3-dihydrobenzothiophene-1, 1-dioxide, aclonifen, clomazone, amitrole, glyphosate (including salts such as sodium, amine, propylamine, isopropylamine, dimethylamine or trimesium), vilanafos, Glufosinate (including salts such as amines or sodium), ashram, propyzamide (prop zamide, tebutam, chlorthal-dimethyl, benfluralin, butralin, dinitramine, ethalfluralin, fluchlorinin, fluchlorin. (Pendimethalin), prodiamine, trifluralin, amiprofos-methyl, butamifos, dithiopyr, thiazopymid, thiazopyramid ), Chlorpropham (chlorpropham), propham (propham), Sueppu (swep), Karubuchireto (karbutilate), Jifenamido (diphenamid), napropamide (napropamide), naproanilide (

naproanilide, acetochlor, alachlor, butachlor, butenachlor, diethyl-ethyl, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor. ), Metazachlor, metolachlor, metolachlor, petoxamide, pretilachlor, propachlor, propisochlor, or S-metolachlor Nylchlor, flufenacet, mefenacet, fentrazamide, fenoxasulfone, pyroxasulone, isoxaben, isoxaben, isoxaben , Flupoxam, dinoterb, DNOC (including salts such as amines or sodium), benfrateate, etofumesate, dalapon, flupropanate, CA Including salts such as thorium, calcium or ammonia), benzulide, butyrate, cycloate, dimpiperate, EPTC, esprocarb, molinate, orbencarb (Pebulate), prosulfocarb, thiobencarb, thiocarbazil, tri-allate, vernarate, chloramben, 2,3,6-TBA, dican dicamba) (amine, diethylamine, isopropyl) (Including salts such as pyramine, diglycolamine, sodium or lithium), 2,4,5-T, 2,4-D (including salts such as amine, diethylamine, triethanolamine, isopropylamine, sodium or lithium) 2,4-DB, chromeprop, dichloroprop, dichloroprop-P, MCPA, MCPA-thioethyl (MCPA-thioethyl), MCPB (sodium salt, ethyl ester, etc.) ), Mecoprop (including salts of sodium, potassium, isopropylamine, triethanolamine, dimethylamine, etc.), mecoprop-P · potassium salt (mecoprop-P), clopyralide (clo yralid, fluroxypyr, picloram, triclopyr, triclopyr-butotyl, quinclorac, quinmerac salt, quintalam salt Diflufenzopyr, flamprop-M (including methyl, ethyl, isopropyl ester), flampprop (including methyl, ethyl, isopropyl ester), chlorflurenol (Chlorfluoren-methyl), cinmethylin, cumylron (c myluron, daimuron, methyldymuron, difenzoquat, etobenzanide, fosamine, folimine, pirobiccarb, oxadi, Code number), aminocyclopyrchlor, cyanamide, heptamaloxyloglucan, indaziflam, triaziflamin, triaziflamin e), endothal disodium salt, phenisopham, BDPT (BDPT), BAU-9403 (code number), SYN-523 (code number), SYP-249 (code number), JS- 913 (code number), IR-6396 (code number), methiozoline, triamonone, HW-02 (code number), BCS-AA10579 (code number), flufenpyr-ethyl, pro Profluzol, pyraclonil, SYP-298 (code number), SYP-300 (code number), beflubutamide (beflubutamide) , Fluridone, flurochloridone, flurtamone, anilofos, bromobutide, caffentropho, indanophenocarb, indanofen And compounds such as benazoline.

Particularly preferred compounds as the herbicidal active compound of the component (B) are:
For example, sulfonylurea compounds such as bensulfuron methyl, pyrazosulfuron ethyl, halosulfuron methyl, azimusulfuron, synosulfuron, cyclosulfamuron, flucetosulfuron, imazosulfuron, ethoxysulfuron, or propyrisulfuron;
For example, sulfonamide compounds such as penox slam;
Chloroacetanilide compounds such as butachlor, pretilachlor or tenyl chlor;
For example, thiocarbamate compounds such as thiobencarb, esprocarb or molinate;
For example, pyrimidinyloxy (thio) benzoic acid compounds such as pyriminobacmethyl, pyriftalide, bispyribac sodium or pyribenzoxime;
For example, tetrazolinone compounds such as fentolazamide;
For example, triazole compounds such as cavenstrol or ipfencarbazone;
For example, pyrazole compounds such as pyrazolate, pyrazoxifene, pyraclonyl or benzophenap;
For example, cyclohexanedione compounds such as benzobicyclone, mesotrione or tefryltrione;
For example, phenoxycarboxylic acid compounds such as 2,4-D, MCPA, MCPB, or chromeprop;
Oxazinone compounds such as oxadichromemephone;
For example, difluoromethanesulfonylanilide compounds such as pyrimisulphan;
For example, isoxazoline compounds such as phenoxasulfone or pyroxasulfone;
Or salts thereof;
Is mentioned.

Most of the component (B) used in the herbicidal composition of the present invention is, for example, published by The Pesticide Manual 14th edition [British Crop Protection Council]. 2006], WO94 / 008999, WO00 / 021924, and WO03 / 061388.

Pyrimisulphan, that is, N- [2- [4,6-dimethoxypyrimidin-2-yl (hydroxy) methyl] -6- (methoxymethyl) phenyl] difluoromethanesulfonamide is described in WO 00/006553. Has been.

Phenoxasulfone, that is, 3- (2,5-dichloro-4-ethoxybenzylsulfonyl) -4,5-dehydro-5,5-dimethoxyisoxazole is described in WO01 / 012613.

Pyroxasulfone, ie 3-[(5-difluoromethoxy-1-methyl-3-trifluoromethylpyrazol-4-yl) methylsulfonyl] -4,5-dihydro-5,5-dimethylisoxazole, It is described in WO02 / 062770.

On the other hand, examples of the salt include a salt of an alkali metal such as sodium or potassium; a salt of an alkaline earth metal such as calcium, magnesium or barium; a salt of a transition metal such as manganese, copper, zinc or iron; an ammonium salt; Salts with inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid; C1-C4 alkyl sulfonic acids such as methane sulfonic acid, aromatic sulfonic acids such as benzene sulfonic acid or toluene sulfonic acid, oxalic acid, maleic acid And salts with organic acids such as fumaric acid, lactic acid, tartaric acid, adipic acid or benzoic acid.

In addition, in the herbicidal composition of the present invention, a herbicidally active compound other than the above may be used in combination.

In the herbicidal composition of the present invention, the use ratio of the component (A) and the component (B) can be appropriately changed depending on the type of both, the type and growth period of the target crop, for example, the transplanting period in rice and the like. However, the mass of the component (A) is usually 0.1 to 200 times the mass of the component (B).

In the herbicidal composition of the present invention, the application amount of the component (A) is not particularly limited, but is usually 10 to 5000 g, preferably 50 to 3000 g, more preferably 100 to 2000 g per hectare of farmland. Is selected within the range.

In the herbicidal composition of the present invention, the application amount of the component (B) is not particularly limited, but usually per hectare of farmland,
For sulfonylurea compounds, 1 to 200 g, preferably 5 to 100 g,
For sulfonamide compounds, 5 to 50 g, preferably 10 to 30 g,
In the case of chloroacetanilide compounds, 50 to 3000 g, preferably 100 to 2000 g,
For thiocarbamate compounds, 500 to 5000 g, preferably 1000 to 4000 g,
For pyrimidinyloxy (thio) benzoic acid compounds, 5 to 500 g, preferably 10 to 200 g,
For tetrazolinone compounds, 50 to 1000 g, preferably 100 to 500 g,
For triazole compounds, 50 to 1000 g, preferably 100 to 500 g,
For pyrazole compounds, 100 to 5000 g, preferably 500 to 3000 g,
For cyclohexanedione compounds, 5 to 1000 g, preferably 10 to 500 g,
In the case of a phenoxycarboxylic acid compound, 50 to 2000 g, preferably 100 to 1000 g,
For oxazinone compounds, 5 to 200 g, preferably 10 to 100 g,
For difluoromethanesulfonylanilide compounds, 5 to 200 g, preferably 10 to 100 g,
For isoxazoline compounds, 50 to 1000 g, preferably 100 to 500 g,
Is selected within the range.

The herbicidal composition of the present invention can contain additive components usually used in agricultural chemical formulations as necessary. As this additional component, a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Examples include disintegrants and decomposition inhibitors. In addition, you may use a preservative, a plant piece, etc. as an additional component as needed. These additive components may be used alone or in combination of two or more.

The above additive components will be described. Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride Salts: Organic solid carriers such as synthetic silicic acid, synthetic silicates, starches, celluloses, plant powders; plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, and the like.

Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Such alcohols; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone; ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, adipic acid Esters such as dimethyl, lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethylsulfoxide; soybean oil, rapeseed Examples include vegetable oils such as oil, cottonseed oil and castor oil; water and the like.

Examples of the surfactant include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene Ethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid Bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkyl Nonionic surfactants such as styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine surfactant, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil Alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate Alkylnaphthalene sulfonate, formalin condensate salt of naphthalene sulfonic acid, formalin condensate salt of alkyl naphthalene sulfonic acid, fatty acid salt, polycalar Anionic surfactants such as phosphate, N-methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate; laurylamine hydrochloride, stearylamine hydrochloride , Cationic surfactants such as alkylamine salts such as oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, polyoxyethylene alkylamine, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride; amino acid type or betaine Examples include amphoteric surfactants such as molds.

Examples of binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6000. Examples include polyethylene glycol having a molecular weight of ˜20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and phospholipids (for example, cephalin and lecithin).

Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, welan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound and water-soluble polysaccharide; high-purity bentonite, fumed silica Inorganic fine powder such as (fumed silica, white carbon).

Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

Examples of the spreading agent include silicone surfactant, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinyl pyrrolidone, maleic acid and styrene copolymer, (meth) acrylic acid copolymer And a half ester of a polymer composed of a polyhydric alcohol and a dicarboxylic anhydride, a water-soluble salt of polystyrene sulfonic acid, and the like.

Examples of the spreading agent include paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.

Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (fumed silica, white carbon), ester gum, and petroleum resin.

Examples of disintegrating agents include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride Examples include acid copolymers and starch / polyacrylonitrile graft copolymers.

Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide, and UV absorbers such as salicylic acid and benzophenone.

Examples of the preservative include potassium sorbate, 1,2-benzthiazolin-3-one and the like.

Examples of plant pieces include sawdust, coconut husk, corn cob, and tobacco stem.

When the herbicidal composition of the present invention contains the above-mentioned additional components, the content is usually 5 to 95% for the carrier, preferably 20 to 90%, and usually 0.1% to about 10% for the surfactant. It is selected in the range of 30%, preferably 0.5 to 10%, and other additives in the range of 0.1 to 30%, preferably 0.5 to 10%.

The herbicidal composition of the present invention may be any solution, emulsion, wettable powder, powder, oil, granular wettable powder, flowable powder, milk suspension, granule, jumbo drug, suspoemulsion, microcapsule, etc. It is used by formulating into a dosage form. At the time of the formulation, a mixed composition with agrochemicals other than the component (B), for example, other herbicides, insecticides, fungicides, plant growth regulators, fertilizers and the like can also be obtained.

Further, the herbicidal composition of the present invention may be in a form in which the above-mentioned arbitrary preparation is packaged with a water-soluble film, and when applied in this form, it can contribute to labor saving and increase safety.

The herbicidal composition of the present invention can be applied at any time from the occurrence of weeds to the growing season to express both weed control and reduction of phytotoxicity to the target crop. Is preferred because the application effect of the herbicidal composition of the present invention is most remarkable.

On the other hand, in the method for reducing the phytotoxicity of crops by the herbicidal active compound of the present invention, the component (A) and the component (B) may be applied simultaneously or in close proximity. Here, the proximity application means that the component (A) is applied while the period from the application of the component (B) is approached before the phytotoxicity of the target crop due to the component (B) is not manifested. For simultaneous application, it can be applied in the form of a ready mix. For example, the pre-formulated composition of the present invention may be used, or the component (A) and the component (B) may be used separately. And can be applied in the form of an in-situ formulation that is mixed at the time of use, ie in the form of a tank mix.

Although the manufacturing method in particular of the herbicidal composition of this invention is not restrict | limited, Usually, the following methods are used.
(1) A method of adding an appropriate amount of water to a mixture of all raw materials, kneading, extruding from a screen with a hole of a certain size, granulating and drying.
(2) A method in which a safener, a herbicidal active compound and a surfactant are dissolved or suspended in an organic solvent and adsorbed on a carrier.
(3) A method of mixing and pulverizing a mixture of all raw materials with an appropriate pulverizer.

Next, the best mode for carrying out the present invention will be described by way of examples, but the present invention should not be limited to these.

Examples 1 to 16
Hydroponic test Murashige / Skoog medium salt (made by Wako Pure Chemical Industries, Ltd.) 25% aqueous solution of various safeners, that is, (A) component is added to a concentration of 10ppm, and a predetermined amount of weeding The active ingredient, ie component (B), was added. 50 mL of this solution was dispensed into an Erlenmeyer flask to prepare various liquid media. Similarly, a liquid medium (hereinafter referred to as “untreated medium”) containing 50 mL of a 25% salt aqueous solution for Murashige-Skoog medium was prepared. Rice (Kinnan style) grown to the second leaf stage in the seedling culture soil was cut leaving a root portion of 2 cm in length. Rice having a cut root was immersed in the above medium and grown in a growth chamber under the conditions of 25 ° C., light period: 16 hours, dark period: 8 hours. After 7 days, the root length was measured. The average value (n = 3) of the measured values was taken, and the percentage (non-treated group ratio) with respect to the average value of the measured values of the untreated group was determined. The results are shown in Tables 1 and 2.

Comparative Examples 1-5
(A) The rice which cut | disconnected the root part to the length of 1 cm beforehand was grown by the liquid culture medium prepared like the Example except not having added the component, and the length of the root part was measured 7 days afterward. The average value (n = 3) of the measured values was taken, and the percentage (non-treated group ratio) with respect to the average value of the measured values of the untreated group was determined. The results are shown in Tables 1 and 2.

The “untreated section” means a crop classification in which the crop is grown on the untreated medium.

 

 

As is apparent from Table 1, it can be seen that the root of the rice of the example is longer than that of the comparative example, and the phytotoxicity of root suppression is reduced.

Examples of various preparations of the composition of the present invention are shown below. In the following description, “part” means “part by mass”.

Example 17
Add appropriate amount of water to 2 parts of 3,5-di-tert-butylcatechol, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 69 parts of calcium carbonate. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylcatechol and phenoxasulfone were obtained.

Example 18
Add an appropriate amount of water to 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 66 parts of calcium carbonate. After kneading, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzoic acid and phenoxasulfone were obtained.

Example 19
Appropriate amounts of 10 parts 3,5-di-tert-butyl-4-hydroxybenzoic acid, 2 parts phenoxasulfone, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 61 parts calcium carbonate After adding water and kneading, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butyl-4-hydroxybenzoic acid and phenoxasulfone were obtained.

Example 20
Add 10 parts of 3,5-di-tert-butylaniline, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 61 parts of calcium carbonate and knead with appropriate amount of water. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylaniline and phenoxasulfone were obtained.

Example 21
Add appropriate amount of water to 10 parts of 3,5-di-tert-butylbenzyl alcohol, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 61 parts of calcium carbonate. After kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzyl alcohol and phenoxasulfone were obtained.

Example 22
Add appropriate amount of water to 20 parts of 2,5-di-tert-butylhydroquinone, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 51 parts of calcium carbonate. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. The granules containing 2,5-di-tert-butylhydroquinone and phenoxasulfone were obtained by drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving.

Example 23
Impact grinding of 10 parts of 2,5-di- (1,1-dimethylpropyl) hydroquinone, 10 parts of phenoxasulfone, 5 parts of fumed silica (white carbon), 10 parts of sodium salt of alkylnaphthalene sulfonate and 65 parts of clay A wettable powder containing 2,5-di- (1,1-dimethylpropyl) hydroquinone and phenoxasulfone was obtained by mixing and grinding using a machine.

Example 24
Wet 2 parts 3,5-di-tert-butylbenzoic acid, 4 parts phenoxasulfone, 5 parts polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts propylene glycol, 0.3 part xanthan gum and 78.7 parts water A flowable agent containing 3,5-di-tert-butylbenzoic acid and phenoxasulfone was obtained by mixing and pulverizing glass beads as a pulverizing medium using a pulverizer.

Example 25
Appropriate amount for 8 parts of 3,5-di-tert-butylbenzoic acid, 8 parts of phenoxasulfone, 3 parts of enzyme-modified dextrin, 3 parts of acetylenic diol, 12 parts of water-containing plastic hollow beads, 20 parts of anhydrous sodium sulfate and 46 parts of urea After adding water and kneading, extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator. Floating diffusion type containing 3,5-di-tert-butylbenzoic acid and phenoxasulfone after sizing to a length of 3-20 mm, dried in a fluidized bed dryer at 60 ° C., and sieved A granule was obtained.

Example 26
To 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of phenoxasulfone, 1 part of bensulfuron methyl, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 65 parts of calcium carbonate After an appropriate amount of water was added and kneaded, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzoic acid, phenoxasulfone and bensulfuron methyl were obtained.

Example 27
Extruded granulation after kneading an appropriate amount of water into 10 parts of 3,5-di-tert-butylcatechol, 1 part of pyrimisulphan, 3 parts of pregelatinized starch, 1 part of sodium dodecylbenzenesulfonate and 85 parts of clay Extrusion granulation was carried out from a screen having an opening diameter of 1 mm using a machine. Granules containing 3,5-di-tert-butylcatechol and pyrimylsulfan were obtained by drying with a fluid bed dryer at a product temperature of 60 ° C. and sieving.

Example 28
Wet 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of pyrimylsulfan, 5 parts of polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and 77.7 parts of water A flowable agent containing 3,5-di-tert-butylbenzoic acid and pyrimisulfurphan was obtained by mixing and pulverizing glass beads using a pulverizer as a pulverizing medium.

Example 29
Appropriate amount of water in 2 parts of 3,5-di-tert-butylcatechol, 3 parts of pyrimyl fan, 3 parts of enzyme-modified dextrin, 3 parts of acetylenic diol, 12 parts of water-containing plastic hollow beads, 20 parts of anhydrous sodium sulfate and 57 parts of urea After kneading and extruding, extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator. Floating diffusion type granules containing 3,5-di-tert-butylcatechol and pyrimylsulfane by sizing to a length of 3-20 mm, drying in a fluid bed dryer at a product temperature of 60 ° C., and sieving. An agent was obtained.

Example 30
Add appropriate amount of water to 10 parts 3,5-di-tert-butylbenzyl alcohol, 1 part pyriminobac-methyl, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 62 parts calcium carbonate. After kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzyl alcohol and pyriminobac-methyl were obtained.

Example 31
3,5-di-tert-butylbenzoic acid 10 parts, pyriminobacmethyl 2 parts, bensulfuron methyl 3 parts, enzyme-modified dextrin 3 parts, acetylene diol 3 parts, hydrous plastic hollow beads 12 parts, anhydrous sodium sulfate 20 parts After adding an appropriate amount of water to 47 parts of urea and kneading, extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator. After sizing to a length of 3 to 20 mm, drying in a fluidized bed dryer at a product temperature of 60 ° C. and sieving, 3,5-di-tert-butylbenzoic acid, pyriminobacmethyl and bensulfuronmethyl are obtained. The contained floating diffusion type granule was obtained.

Example 32
3,5-di-tert-butylbenzyl alcohol 5 parts, thiobencarb 5 parts, enzyme-modified dextrin 1 part, dioctyl sulfosuccinate sodium salt 1 part, fumed silica (white carbon) 5 parts, diatomaceous earth 10 parts, bentonite 25 parts After adding an appropriate amount of water to 48 parts of calcium carbonate and kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. The granules containing 3,5-di-tert-butylbenzyl alcohol and thiobencarb were obtained by drying with a fluid bed dryer at a product temperature of 50 ° C. and sieving.

Example 33
After kneading an appropriate amount of water in 10 parts of 2,5-di-tert-butylhydroquinone, 3 parts of fentolazamide, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 60 parts of calcium carbonate Extrusion granulation was performed from a screen having an aperture diameter of 1 mm using an extrusion granulator. The granules containing 2,5-di-tert-butylhydroquinone and fentolazamide were obtained by drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving.

Example 34
Wet pulverize 10 parts of 3,5-di-tert-butylhydroquinone, 1 part of oxadichromephone, 5 parts of polyoxyethylene styryl phenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and 73.7 parts of water. The flowable agent containing 3,5-di-tert-butylhydroquinone and oxadichromemephone was obtained by mixing and grinding the glass beads as a grinding medium.

Example 35
35 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of caffeentrol, 4 parts of benzobicyclone, 5 parts of polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and water Seven parts were mixed and pulverized using glass beads as a pulverization medium using a wet pulverizer to obtain a flowable agent containing 3,5-di-tert-butylbenzoic acid, caffeentrol and benzobicyclone.

Example 36
3,5-di-tert-butylbenzyl alcohol 5 parts, butachlor 5 parts, enzyme-modified dextrin 1 part, dioctyl sulfosuccinate sodium salt 1 part, fumed silica (white carbon) 5 parts, diatomaceous earth 10 parts, bentonite 25 parts After adding an appropriate amount of water to 48 parts of calcium carbonate and kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. Granules containing 3,5-di-tert-butylbenzyl alcohol and butachlor were obtained by drying with a fluid bed dryer at a product temperature of 50 ° C. and sieving.

Example 37
After kneading with 20 parts of 3,5-di-tert-butylcatechol, 1 part of penox slam, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 52 parts of calcium carbonate with an appropriate amount of water. Extrusion granulation was performed from a screen having an aperture diameter of 1 mm using an extrusion granulator. By drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylcatechol and penox slam were obtained.

Example 38
2,5-di- (1,1-dimethylpropyl) hydroquinone 3 parts, oxadichromemephone 1 part, chromeprop 3 parts, polyoxyethylene styrylphenyl ether sulfate sodium salt 5 parts, propylene glycol 10 parts, xanthan gum 0.3 part and water A flowable agent containing 2,5-di- (1,1-dimethylpropyl) hydroquinone, oxadichromemephone and chromeprop was prepared by mixing and grinding 77.7 parts with a glass bead as a grinding medium using a wet grinding machine. Obtained.

Example 39
Appropriate amount of 4 parts 3,5-di-tert-butyl-4-hydroxybenzoic acid, 8 parts benzofenap, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 61 parts calcium carbonate After adding water and kneading, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butyl-4-hydroxybenzoic acid and benzophenap were obtained.

Next, an example of the method for reducing the phytotoxicity of crops by the herbicidal active compound of the present invention will be shown.

Example 40
By mixing and grinding 10 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of alkylnaphthalenesulfonic acid sodium salt, 30 parts of diatomaceous earth and 58 parts of clay using an impact pulverizer, 3,5-di- A wettable powder containing tert-butylbenzoic acid was obtained. Separately, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 71 parts of calcium carbonate were kneaded with an appropriate amount of water, and then examined using an extrusion granulator. It was extruded and granulated from a screen with an opening diameter of 1 mm. The granules containing phenoxasulfone were obtained by drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving. This wettable powder and granule were simultaneously applied to paddy weeds.

Example 41
The granule containing phenoxasulfone produced in Example 40 was applied to paddy weeds, and after 3 days, the wettable powder containing 3,5-di-tert-butylbenzoic acid produced in Example 40 was added. Applied to paddy weeds.

Example 42
The wettable powder containing 3,5-di-tert-butylbenzoic acid produced in Example 40 was applied to paddy weeds, and after 7 days, the granule containing phenoxasulfone produced in Example 40 was used. Applied to paddy weeds.

Claims (22)

1. Formula (I)
   

   

   
   (Wherein R ¹ represents a hydrogen atom, a hydroxyl group or a C4-C5 alkyl group, R ² represents a hydrogen atom or a C4-C5 alkyl group, R ³ represents a C4-C5 alkyl group, and X represents a carboxyl group. Represents an amino group, a hydroxyl group or a hydroxymethyl group, and Y represents a hydrogen atom or a hydroxyl group, wherein either R ¹ or R ² is a C4-C5 alkyl group.
   A herbicide safener characterized by comprising a compound represented by
2. The herbicide safener according to claim 1, wherein R ¹ is a hydrogen atom or a hydroxyl group, R ² and R ³ are C4 to C5 alkyl groups, and Y is a hydrogen atom or a hydroxyl group.
3. The herbicide phytotoxicity alleviation according to claim 1, wherein R ¹ is a hydrogen atom, R ² and R ³ are C4-C5 alkyl groups, X is a carboxyl group, and Y is a hydrogen atom or a hydroxyl group. Agent.
4. The herbicide phytotoxicity according to claim 1, wherein R ¹ is a hydrogen atom, R ² and R ³ are C4 to C5 alkyl groups, X is an amino group or a hydroxymethyl group, and Y is a hydrogen atom. Relief agent.
5. The herbicide safener according to claim 1, wherein R ¹ is a hydroxyl group, R ² and R ³ are C4-C5 alkyl groups, X is a hydroxyl group, and Y is a hydrogen atom.
6. The herbicide safener according to claim ^1, wherein R ¹ and R ³ are C4-C5 alkyl groups, R ² is a hydrogen atom, and X and Y are hydroxyl groups.
7. The herbicide safener according to any one of claims 1 to 6, wherein the C4 to C5 alkyl group is a tert-butyl group or a 1,1-dimethylpropyl group containing a quaternary carbon.
8. (A) a herbicide safener according to any one of claims 1 to 7;
   (B) sulfonylurea compounds, sulfonamide compounds, chloroacetanilide compounds, thiocarbamate compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds One or more herbicidal active compounds selected from phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds and isoxazoline compounds, or salts thereof,
   A herbicidal composition with reduced phytotoxicity.
9. 9. The phytotoxicity according to claim 8, wherein the sulfonylurea compound is bensulfuron methyl, pyrazosulfuron ethyl, halosulfuron methyl, azimusulfuron, synosulfuron, cyclosulfamuron, flucetosulfuron, imazosulfuron, ethoxysulfuron or propyrisulfuron. Herbicidal composition with reduced weight.
10. The herbicide composition with reduced phytotoxicity according to claim 8, wherein the sulfonamide compound is penoxsulam.
11. The herbicide composition with reduced phytotoxicity according to claim 8, wherein the chloroacetanilide compound is butachlor, pretilachlor or tenyl chlor.
12. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the thiocarbamate compound is thiobencarb, esprocarb or molinate.
13. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the pyrimidinyloxy (thio) benzoic acid compound is pyriminobacmethyl, pyriphthalide, bispyribac sodium or pyribenzoxime.
14. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the tetrazolinone compound is fentolazamide.
15. The herbicide composition with reduced phytotoxicity according to claim 8, wherein the triazole-based compound is caffeentrol or ipfencarbazone.
16. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the pyrazole compound is pyrazolate, pyrazoxifene, pyraclonyl or benzophenap.
17. The herbicide composition with reduced phytotoxicity according to claim 8, wherein the cyclohexanedione compound is benzobicyclone, mesotrione or tefryltrione.
18. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the phenoxycarboxylic acid compound is 2,4-D, MCPA, MCPB, or chromeprop.
19. The herbicide composition with reduced phytotoxicity according to claim 8, wherein the oxazinone compound is oxadiclomephone.
20. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the difluoromethanesulfonylanilide compound is pyrimisulfuran or pyroxasulfone.
21. The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the isoxazoline-based compound is phenoxasulfone or pyroxasulfone.
22. (A) a herbicide safener according to any one of claims 1 to 7;
    (B) sulfonylurea compounds, sulfonamide compounds, chloroacetanilide compounds, thiocarbamate compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds , One or more herbicidal active compounds selected from phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds and isoxazoline compounds, or salts thereof,
    A method for reducing phytotoxicity of crops caused by the herbicidal active compound, wherein the method is applied simultaneously or in proximity.