阅读说明：本技术 杂环酰胺化合物的结晶及其制造方法 (Crystals of heterocyclic amide compound and process for producing the same ) 是由 中屋洁彦 伊与部阳子 小室敬济 于 2020-03-13 设计创作，主要内容包括：本发明的课题是杂环酰胺化合物的结晶及其制造方法。解决手段是阐明了式(1)所示的、作为具有作为除草剂有用的活性的化合物的杂环酰胺化合物具有新的结晶。(The present invention addresses the problem of providing crystals of heterocyclic amide compounds and a method for producing the same. The solution is to clarify that a heterocyclic amide compound represented by the formula (1) has a novel crystal as a compound having an activity useful as a herbicide.)

1. A crystal of the heterocyclic amide compound represented by formula (1) having peaks at diffraction angles 2 theta of 7.29 DEG + -0.2, 12.62 DEG + -0.2, 14.13 DEG + -0.2, 17.51 DEG + -0.2, 18.64 DEG + -0.2, 19.03 DEG + -0.2, 20.56 DEG + -0.2, 20.89 DEG + -0.2, 21.76 DEG + -0.2, 23.37 DEG + -0.2, 25.41 DEG + -0.2, 27.70 DEG + -0.2 and 30.34 DEG + -0.2 in powder X-ray diffraction using Cu-K alpha rays,

2. a composition in suspension comprising the crystallization and dispersion medium of claim 1.

3. A method for controlling weeds, which comprises the step of applying the composition in the form of a suspension according to claim 2 in an amount effective for controlling weeds.

Technical Field

The present invention relates to a 2 [ 2](isopropylsulfonyl) methyl]-N- (5-methyl-1, 3, 4-)Oxadiazol-2-yl) -5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]Pyridine-8-carboxamide [ hereinafter, abbreviated as Compound (1) ]]The novel crystal and a process for preparing the crystal.

Background

The solid state of a chemical compound can be amorphous (i.e., the distance of atoms has no long range order) or crystalline (i.e., the atoms are arranged in an ordered reflective pattern). Furthermore, it has not been possible to predict physicochemical properties such as melting point or solubility of a crystal form in which a solid state of a chemical compound can exist. Furthermore, it has hitherto been difficult to predict whether the solid state of a compound may exist in an amorphous or crystalline state.

On the other hand, the compound (1) contained in the present invention is known as one of heterocyclic amide compounds useful as herbicides (for example, see patent documents 1 to 4).

Documents of the prior art

Patent document

Patent document 1: international publication No. 2014/192936

Patent document 2: japanese patent laid-open publication No. 2016-153397

Patent document 3: japanese laid-open patent publication No. 2017-025054

Patent document 4: japanese patent laid-open publication No. 2019-019118

Disclosure of Invention

Problems to be solved by the invention

In general, it has not been possible to produce a specific crystal of a compound and to predict physical properties such as melting point and water solubility of the obtained crystal.

The purpose of the present invention is to provide a novel crystal of compound (1) and a method for producing the same.

Means for solving the problems

The present inventors have conducted intensive studies and, as a result, have found that the compound (1) has a novel crystal. That is, the present invention relates to crystals of the compound (1) described in [ 1] to [ 4] below (hereinafter, simply referred to as "crystals of the present invention"), compositions containing the crystals of the present invention described in [ 5 ] to [ 8 ] below (hereinafter, simply referred to as "compositions of the present invention"), and a method for controlling weeds using the crystals of the present invention described in [ 9 ] to [ 10 ] below.

〔1〕

Crystals of the heterocyclic amide compound represented by formula (1) have peaks at diffraction angles 2 θ of 7.29 ° ± 0.2, 12.62 ° ± 0.2, 14.13 ° ± 0.2, 17.51 ° ± 0.2, 18.64 ° ± 0.2, 19.03 ° ± 0.2, 20.56 ° ± 0.2, 20.89 ° ± 0.2, 21.76 ° ± 0.2, 23.37 ° ± 0.2, 25.41 ° ± 0.2, 27.70 ° ± 0.2, and 30.34 ° ± 0.2 in powder X-ray diffraction using Cu — K α rays.

〔2〕

Crystals of the heterocyclic amide compound represented by formula (1) have peaks at diffraction angles 2 θ of 7.29 ° ± 0.1, 12.62 ° ± 0.1, 14.13 ° ± 0.1, 17.51 ° ± 0.1, 18.64 ° ± 0.1, 19.03 ° ± 0.1, 20.56 ° ± 0.1, 20.89 ° ± 0.1, 21.76 ° ± 0.1, 23.37 ° ± 0.1, 25.41 ° ± 0.1, 27.70 ° ± 0.1, 30.34 ° ± 0.1 in powder X-ray diffraction using Cu — K α rays.

〔3〕

The crystal of the heterocyclic amide compound represented by formula (1) has peaks at diffraction angles 2 θ of 7.29 °, 12.62 °, 14.13 °, 17.51 °, 18.64 °, 19.03 °, 20.56 °, 20.89 °, 21.76 °, 23.37 °, 25.41 °, 27.70 °, and 30.34 ° in powder X-ray diffraction using Cu — K α rays.

〔4〕

The crystal of the heterocyclic amide compound according to any one of [ 1] to [ 3] above, which shows a diffraction curve substantially the same as that shown in FIG. 1 of the drawings of the present application in powder X-ray diffraction using Cu-K.alpha.rays.

〔5〕

A pesticidal composition comprising the crystal according to any one of [ 1] to [ 3] above.

〔6〕

A herbicidal composition comprising the crystal according to any one of [ 1] to [ 3] above.

〔7〕

A composition in suspension comprising the crystal according to any one of [ 1] to [ 3] above and a dispersion medium.

〔8〕

An aqueous suspension composition comprising the crystal according to any one of [ 1] to [ 3], a surfactant and water as a dispersion medium.

〔9〕

A method for controlling weeds, which comprises the step of applying an amount of the composition according to any one of [ 5 ] to [ 8 ] above, which is effective for controlling weeds.

〔10〕

The method for controlling weeds described above under [ 9 ], which comprises a step of spraying the stem and leaf of the composition described above under [ 5 ] to [ 8 ] in an amount effective for controlling weeds.

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, the crystals of the compound (1) can be obtained with good reproducibility.

Drawings

FIG. 1 is a powder X-ray diffraction pattern of the crystal of the present invention

FIG. 2 is a differential scanning calorimetry chart of the crystal of the present invention

FIG. 3 is a powder X-ray diffraction pattern of an amorphous compound (1) of reference example 1

FIG. 4 is a differential scanning calorimetry chart of an amorphous body of Compound (1) in reference example 1

Detailed Description

Compound (1) is 3- [ (isopropylsulfonyl) methyl]-N- (5-methyl-1, 3, 4-)Oxadiazol-2-yl) -5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]Pyridine-8-carboxamide, the structure of which is shown below.

The powder X-ray diffraction peaks of the crystals of the present invention are shown below.

2θ＝7.29°、12.62°、14.13°、17.51°、18.64°、19.03°、20.56°、20.89°、21.76°、23.37°、25.41°、27.70°、30.34°。

Further, the error of the powder X-ray diffraction peak is usually ± 0.2, and ± 0.1 may be taken depending on the case, and therefore the peak value of the crystal of the present invention in consideration of the error is usually 7.29 ° ± 0.2, 12.62 ° ± 0.2, 14.13 ° ± 0.2, 17.51 ° ± 0.2, 18.64 ° ± 0.2, 19.03 ° ± 0.2, 20.56 ° ± 0.2, 20.89 ° ± 0.2, 21.76 ° ± 0.2, 23.37 ° ± 0.2, 25.41 ° ± 0.2, 27.70 ° ± 0.2, 30.34 ° ± 0.2, and depending on the case, 2 θ is 7.29 ° ± 0.1, 12.62 ° ± 0.1, 14.13 ° ± 0.1, 17.51 ° ± 0.1, 18.64 ° ± 0.1, 19.03 ° ± 0.1, 20.76 ° ± 0.1, 27.1, 27.35 ° ± 0.1, 27.1, 3 ° ± 0.1.1, 3 ° ± 0.2.

The measurement conditions of the powder X-ray diffraction peaks shown above are as follows.

[ powder X-ray diffraction ]

The device comprises the following steps: x' PERT-PRO MPD (スペクトリス Kabushiki Kaisha)

The determination method comprises the following steps: transmission method

X-ray: Cu-K alpha

Voltage: 45kV

Current: 40mA

Sampling interval: 0.0070deg

Data range: 2 theta 5 to 40deg

The melting point of the crystal is 216-218 ℃, and an endothermic peak in a low temperature region compared with the melting point is not observed in differential scanning calorimetry.

The conditions for differential scanning calorimetry in the melting point measurement shown above are as follows.

[ differential scanning calorimetry measurement conditions ]

The device comprises the following steps: DSC-60 (manufactured by Shimadzu Kagaku Co., Ltd.)

And (3) heating: 20 deg.C- (10 deg.C/min) -450 deg.C

Atmosphere: nitrogen gas

Comparison: al (Al)₂O₃

A container: SUS-made products

Sampling: 1 second

Next, a method for producing the crystal of the present invention will be described below.

The crystals of the present invention can be obtained by a method in which the compound (1) is dissolved in a solvent by heating and the obtained solution is crystallized by slowly cooling, or a method in which the solvent is distilled off from the obtained solution and crystallized. The solvent used may be any solvent which is inactive with respect to the compound (1), and examples thereof include diethyl ether, methyl-t-butyl ether, tetrahydrofuran, dimethoxymethane, diethoxymethane, 1, 2-dimethoxyethane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, and 1, 4-diethylene glycol dimethyl etherEther solvents such as alkanes, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, 2-methyl-2-propanol, methyl cellosolve, ethyl cellosolve, isopropyl cellosolve, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, cyclohexanol, benzyl alcohol, alcohol solvents such as n-pentane, n-hexane, cyclohexane, methylcyclohexane, n-heptane, n-octane, and n-decaneAliphatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, nitrobenzene, and tetrahydronaphthalene, nitrile solvents such as acetonitrile and propionitrile, ester solvents such as methyl acetate, ethyl acetate, butyl acetate, and ethyl propionate, halogenated hydrocarbon solvents such as methylene chloride, chloroform, carbon tetrachloride, 1, 2-dichloroethane, and 1,1, 2-trichloroethane, amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone, urea solvents such as1, 3-dimethylimidazolidinone, and N, N, N ', N' -tetramethylurea, sulfur-containing polar solvents such as dimethyl sulfoxide and sulfolane, pyridine solvents such as 2-picoline, 3-picoline, 4-picoline, and 5-ethyl-2-picoline, pyridine solvents such as dimethyl sulfoxide and sulfolane, and the like, Ketone solvents such as acetone, methyl ethyl ketone, diethyl ketone and methyl isobutyl ketone, and water, and these solvents may be used alone or in combination of 2 or more. Among these solvents, preferred are ether solvents, aromatic hydrocarbon solvents, ester solvents, halogenated hydrocarbon solvents, and amide solvents, and more preferred is 1, 4-bisAlkane, toluene, ethyl acetate, 1, 2-dichloroethane, and N, N-dimethylformamide.

The amount of the solvent used is usually 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight, based on1 part by weight of the compound (1).

The temperature for dissolving the compound (1) in the solvent is usually 30 to 150 ℃, preferably 30 to 100 ℃.

The cooling rate is usually 0.1 to 80 ℃/hr, preferably 1 to 60 ℃/hr, and any cooling rate can be optionally changed within the above range.

The temperature of the solution when the precipitated crystals are taken out is usually-30 to 50 ℃ and preferably-20 to 30 ℃.

The time required for crystallization is usually 0.1 to 100 hours, preferably 1 to 50 hours.

In addition, in the case of distilling off the solvent, it can be distilled off by heating at atmospheric pressure up to the boiling point of the solvent or more. Further, by adjusting the degree of reduced pressure in the vessel, the solvent can be distilled off at an arbitrary temperature up to the boiling point of the solvent under reduced pressure.

The crystal of the present invention is superior to the amorphous compound (1) in terms of characteristics such as chemical stability, photostability, hygroscopicity, suspendability, filterability, and the like, and manufacturing characteristics such as removability of a residual solvent.

Next, the composition of the present invention will be described in detail.

When the composition of the present invention is an aqueous suspension-type agricultural chemical composition, water or an organic liquid in which the crystal of the present invention is hardly soluble can be used as a dispersion medium that can be used. Examples of the organic liquid include alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and isopropyl alcohol, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as γ -butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, aromatic hydrocarbons such as xylene, alkylbenzene, phenylxylylethane, and alkylnaphthalene, aliphatic hydrocarbons such as machine oil, N-paraffin, isoparaffin, and cycloparaffin, mixtures of aromatic hydrocarbons such as kerosene and aliphatic hydrocarbons, and oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, and castor oil.

The content of the crystal of the present invention is usually 0.1 to 50 parts by weight, and more preferably 1 to 30 parts by weight, based on 100 parts by weight of the composition of the present invention.

In addition, in addition to the crystal of the present invention, 1 or more kinds of known agricultural chemicals, for example, herbicides, safeners, insecticides, acaricides, nematicides, antiviral agents, plant growth regulators, bactericides, synergists, attractants, repellents and the like may be further contained, and in this case, more excellent control effects can be exhibited. As well-known pesticides, herbicides, safeners, bactericides, nematicides and insecticides are particularly preferred. Specifically, the following description will be made if its common name is exemplified, but the present invention is not necessarily limited thereto.

Herbicide: 4-CPA, salts of 4-CPA (4-CPA-salts), 4-CPB, 4-CPP, 2,4-D (2,4-PA), salts of 2,4-D (2,4-D-salts), esters of 2,4-D (2,4-D-esters), 3,4-DA, 2,4-DB, salts of 2,4-DB (2,4-DB-salts),Esters of 2,4-DB (2,4-DB-esters), 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,4,5-T, salts of 2,4,5-T (2,4,5-T-salts), esters of 2,4,5-T (2,4,5-T-esters), 2,4,5-TB, 2,3,6-TBA (TCBA), salts of 2,3,6-TBA (2,3,6-TBA-salts), acetochlor (acetochlor), acifluorfen-ethyl (acifluorfen), acifluorfen-methyl ester (acifluorfen-methyl), acifluorfen-sodium salt (acifluorfen-sodium), phenyl ether (acifluorfen), acrolein (acifluorfen), alachlor (acifluorfen), dipropyl chloride (Acfluorfen-methyl), dipropyl chloride (CDalloxan), salts of butachlor (CDalloxan), salts of Acfluorfen-methyl ester (Acfluorfen-methyl), Acfluorfen-sodium salt (Acfluorfen-sodium salt), Acrylamide (Acrylamide), Acrylamide (Acrylamide, or Acrylamide, or, Allyl alcohol (allylalcohol), pentachlorothioic acid (alorac), metribuzin (ametryn), ametryn (ametryn), tebufenon (amibuzin), amicarbazone (amicarbazone), alachlor (amicochlor), amidosulfuron (amicarbazone), chloropyrimidine (amicarbazochrome), methyl clofenamate (amicarbazochrome), potassium chloropyrimidine-potassium salt (amicarbazochrome-potassiurn), aminopyralid (amicarbazalid), amicarbazone (amicarbazone-methyl), propulfos (amicarbazone), amicarbazone (ammonium), amicarbazone (amicarbazone), pyrithion (azothion), pyrithion (azobenzosulfuron), pyrithion (azothion (azobenzoxim), pyrithion (azon), pyrithion (azone (amicarbazone), ametryn (amicarbazone), ames), ametryn (amicarbazone), ames), pyrithion (amicarbazone), ames), pyrithion (amicarbazone), pyrithion (amicarbazone), pyrithion (amicarbazone) salts of chlorazone, pyrithion (amicarbazone), pyrithion (amicarbazone), pyrithion (amicarbazone) and pyrithion (amicarbazone) salts of pyrithion), pyrithion (amicarbazone) salts of pyrithion (amicarbazone), pyrithion (amicarbazone), pyrithion (amicarbazone) and pyrithion (amicarbazone), pyrithion (amicarbazone) salts of pyrithion), pyrithion (amicarbazone) salts of pyrithion, pyribenazolone), pyrithion (amicarbazone) and pyrithion (amicarbazone), pyrithion (amicarbazone), pyrithion (amicarbazone) and pyrithion (amicarbazone), pyrithion (amicarbazone), pyrithion (amicarbazone) and pyrithion (amicarbazone), pyrithion (amicarbazone, pyrithion (amicarbazone), pyrithio, Flubendiamide (beflubutamid-M), benazolin acid (benazolin), benazolin-ethyl, benazolin-sodium, benfuresate (benfuresate), bensulfuron-methyl, bensulide (bensulide, SAP), bentazon (bentazon, bentazone), bentazone sodium (bentazone-sodium), benfurazone (bentranin), bensulfuron-methyl, bensultap (bentazon-methyl), bentazone (bentazone-ammonium), bensulide (bensulam), bensulam (bensulam-ammonium, bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), bensulam (bensulam), benZoylprop-ethyl), benzthiazuron (benthiazuron), fluoxyfen (bicyclophoron), bifenox (bifenox), bialaphos (bilanafos, bialaphos), bialaphos (bilanafos-sodium), binafosinate (bilanafos-sodium), binapacryl (binapacryl), bispyribac (bispyribac-sodium), ビクスロゾン (bixozone) sodium tetraborate decahydrate (borax), bromacil (brofenadine), salts of bromacil (brofenamide-salts), furoyl cyanide (bromobonil), butyryl cyanide (brofenbuthionide), bromophenol (brofenamide), ブロモピラゾン (broxypyrazon), bromoxynil (broxytralkoxydim), bromoxynil (bromoxynil), bromoxynil potassium salt (brofenflurate-potassium), butralin (butralin-butyl-sodium), butralin (butralin-butyl-ethyl, butyl-ethyl, butyl-ethyl, butyl-, Buthylate (buthylate), cafenstrole (cafenstrole), calcium cyanamide (calcium cyanamide), clofenacet (camfendiclol), calcium chlorate (calcium chloride), chlorsulfuron (carbasulam), fenpyroxate (carbazamide), fenoxaprop (carboxazole), carfentrazone-ethyl (carfentrazone-ethyl), CDEA, CEPC, metoxyfen (chloroxyfen, chloroxynil), chlorafen (chlorofenuron), chloracetyl (chlorofenethyl), chloran-methyl ester (chlorofenpropi), chlorambucil (chlorofenpyr-methyl), chlorambucil (chlorofenprophen), chlorazone (chlorofenfluridone), chlorambucil (chlorofenpyr-ethyl), chlorambucil (chlororon), chlorambucil-ethyl (chlororon), chlorambucil (chlorobenbenbenbencarb), chlorambucil (chlororon (chlorobenbencarb), chlorambucil (chlororon), chlorambucil (chlorobenbenbenbenbenbenbencarb), benbenbenbencarb (chlorobenbenbenbenbencarb), bencarb (chlororon (chlorobencarb), bencarb (chlorocarb), bencarb (halocarb), bencarb (halocarb), bencarb (halocarb), bencarb (methyl chloride (methyl), bencarb (methyl chloride (methyl), bencarb), bencarb-methyl chloride (methyl chloride, bencarb, Plastic alcohols (chlorotrifluoroethol-methyl), chloranil (chlorotdazon, PAC, pyrazon), chlorimuron-ethyl (chlorimuron-ethyl), chlorpropham (chlorimurine), cumyl ether (chlorimuron, CNP), chloroacetic acid (chloroacetic acid, monochloroacetic acid), sodium chloroacetate (sodium chloroacetate, SMA), chlorotoluron (chlorotoluon), hay-bacillus subtilis), and so onLong (chloroxuron), chlorodinonitrile (chloroxynil), chloranilron (chlorophthalanim), chlorpropham (IPC), chlorsulfuron (chloroxuron), chlorophthalic acid (chlorothal, TCTP), esters of chlorophthalic acid (chlorothal-esters), chlorothiooxamine (chlorothiaamid, DCBN), cinidon-ethyl, cinmethylin (cinmethylin), sulforon (cinsulfuron), pyroxene (cisanilide), chlorophyllin (closyfos), clethodim (clethodim), iodochlordinate (clinodine), clodinafop (clodinafop), clodinafop-propargyl (clodinafop), clodinafop-propyl propionate (clothrobutan-isopropyl), isobuton (closant-isopropyl), clodinyl (clodinafop), clodinafop-isopropyl), clodinafop (closantonin-ethyl), clodinyl (clodinafop-propyl clofenapyr), closanto-isopropyl (closanto-isopropyl), closanto (closanto-ethyl, clodinyl-isopropyl-clodinyl, clodinafop-methyl, clodinyl, clodinafop-isopropyl (clodinafop-isopropyl, clodinyl, or (clodinyl, or (clodinyl, or a, or (clodinyl, or aClomazone, clomeprop, clopropam, clopropaquin, clophysalm, clophym, clopyralid-methyl, clopyralid salts (cloyralid-salts), cloransulam, copper sulfate (2-valent) (coppersulfate), CPMF, CPPC, proparazine, cresols, cumyluron, cyanazine, cyanamid, cyanazine, comorbid, cyclopyranine, シクロピラニル, cy シクロピリモレート, cyropyram, cyclopropamon, sulfometuron, cyclosulfometyl, cyhalon-butyl, cyhalon-methyl, cyhalon (cyhalon-methyl, cyhalon-methyl, cyhalon-methyl, cyhalon-methyl, cyhalon (cyhalon, cyhalon-methyl, cyhalon-methyl, cyhalon-methyl, cyhalo, Cyrochlor (cypromid), desmuron (daimuron, dymron), dalapon (dalapon), salts of dalapon (dalapon-salts), dazomet (dazomet), dazomet sodium salt (dazomet-sodium), butachlor (deachlor), desmedipham (desmedipham), dimethomon (desmetryn), dichlofeninate (di-acrylate), dicamba (dicamba, MDBA), salts of dicamba (dicamba-salts), esters of dicamba (dicamba-esters), dichlobenil (dichlobenil, DBN), ジクロラウレア (dichlorarea, U), benzylamine (DCdichlormate), o-dichlorobenzene (o-dichlorobenzene, DCB), 2, 4-diproprionic acid (dichloruro)P), salts of 2, 4-dichlopropionic acid (dichlorprop-salts), esters of 2, 4-dichlopropionic acid (dichlorprop-esters), 2, 4-dichlopropionic acid (dichloprop-P), salts of 2, 4-dichlopropionic acid (dichloprop-P-salts), esters of 2, 4-dichlopropionic acid (dichloprop-P-esters), diclofop-P-esters, diclofop-P-clo-P-diclol-P-diclol-P-diclol-P-diclol-P-diclol-P-, Diflufenican, diflufenzopyr sodium salt (diflufenzopyr-sodium),Dazomet (dimefuron), dimeflubenz (dimepiperate), dimethenamid (dimethachlo), dimethyethrin (dimethametryn), dimethenamid (dimethenamid-p), dimethenamid (dimethenamid), dinofenate (dinenanate), nitrophenol (dinosp), dinicone (dinosem), dinotefuran (dinoseb, DNBP), salts of dinophenol (dinoseb-salts), esters of dinotefuran (dinoseb-esters), terbenol (dinoteoper), salts of terbenol (dinin-salts), esters of terbinal (dinotefuran-esters), dimeglumide (dimethenamid), dimethenamid (dimethenamid-p), dimethenamid-sodium (dimethenamid-salts), dimethenamid-bromide (dimethenamid-salts), dimethenamid (sodium (dimethenamid, dimethenamid-salts), dimethenamid (dimethenamid, dimethenamid-salts), dimethenamid (dimethenamid, dimethenamid-salts), dimethenamid (dimethenamid, dimethenamid-salts), dimethenamid (dimethenamid, dimethenamid (dimethenamid, dimethenamid-salts), dimethenamid-salts of (dimethenamid, dimethenamid-salts of (dimethenamid, dimethenamid-salts of (dimethenamid, dimethenamid-salts of (dimethenamid, dimethenamid, DMPA, DNOC, salts of DNOC (DNOC-salts), EBEP, metribuzin (eglinazine), liquirizine-ethyl (eglinazine-ethyl), endothal (endothal), salts of endothal (endothal), triazasum (epronaz), EPTC, furazol (erbon), esprocarb (esprocarb), ethachlor (ethachlor), ethalfluorine (ethalflurin), ethametsulfuron (ethametsulfuron), ethametsulfuron (et)halosulfuron-methyl), ethametsulfuron (ethaprochlor), thifensulfuron-methyl (ethidimuron), ethiofen (ethiolate), ethiozin (ethiozin), ethofumesate (ethofumesate), fluroxypyr (ethofuran), ethofenprox (ethofen-ethyl), ethofencuron (ethofencuron), nitrophenol (ethiofen), pyrimethanil (ethopromid), ethofenpyramide (ethofenzanid), EXD, carbosulfan (fenasulam), 2,4, 5-rhinopropionic acid (fenoprop, 2,4,5-TP, silvex), salts of 2,4, 5-rhinopropionic acid (fenoprop-sas), esters of 2,4, 5-rhinopropionic acid (fenoprop-esters), 2,4, 5-rhinopropionic acid (ethofes), salts of 2,4, 5-rhinorrhea (ethofenprox-esters), and esters of thiopropionic acid (ethofenprox-esters),Fenoxaprop-p-ethyl,Fenoxaprop-ethyl and ethylFenoxaprop-p, and mefenpyr-diethylFenoxaprop-p-ethyl and bensulamPyraclonil (fenoxasulfone), quinoxyfen (fenquinotrione), triclosan (fenteracol), thiazoxol (fenteracol), thiazofurazoic acid (fenthiaprop), thiazopyr (fenthiaprop-ethyl), fentrazamide (fentrazamide), ferric sulfate (2-valent) (ferrous sulfate), fenuron (fenuron), fenuron TCA (fenuron-TCA), ryegrass-fluorine (flamprop), esters of ryegrass-esters (flamprop-esters), and semolina-fluorine (flamprop-M), esters of ryegrass fluoride (flamprop-M-esters), flazasulfuron (flazasulfuron), florasulam (florasulam), fluroxypyr (flurpyrauxfen), fluroxypyr (flurpyraux-benzol), fluazifop (fluazifop), fluazifop-P (fluazifop-esters), isopyrap (fluazolate), fluxasulfuron (flucarbazone), fluxasulfuron-methyl.(Flurbazone-sodium), flucetosulfuron (fluetosulfuron), flufluralin (fluorochloralin), flufenacet (flufenacet), diflufenican (flufenacet), flufenacet (flufenacet), flurazinam (flufenoyr), flurazinam-ethyl (flufenpyr), flumetsulam (fluetsulam), flumethazine (fluazin), flumiclorac (fluiclorac), flumetsulam (flunixin), flumetsul (fludioxonil), flumuron (flufenin-sodium), flumetsul (flufenin), flumetsul (fluxon-sodium), flumetsul (flufenim), flumetsul (flufenacet-sodium), flumetsul (flufenacetron (flufenacet), flumetsul (flufenacetron), flumetsul (fluroxypyr), flumetsul (flufenacetron (flufenacet), flumetsul (fluroxypyr), flumetsul (fluridon-sodium, flufenacet (fluridon), fluroxypyr, flufenacet (fluridon), fluroxypyr, flumetsul (fluroxypyr, fluridon (fluroxypyr), fluridon (fluroxypyr), fluroxypyr, fluroxypetryn (fluroxypyr), fluroxypyr, Flazasulfuron sodium salt (flupyrsulfuron-methyl-sodium), fluazinone (fluridone), fludioxonil (fluroxypyr), fluroxypyr (fluroxypyr), esters of fluroxypyr (fluroxypyr), flurtamone (flurtamone), fluthiamide (fluthiamide), fluthiamide methyl ester (fluthiamide), fomesafen (fomesafen), fomesafen sodium salt (fomesafen-sodium), foramsulfuron (fomasulfuron), glufosinate (fosinate), glufosinate-ammonium (fomamine), furazaisofen (furazafen), glufosinate-ammonium (glufosinate-sodium), glufosinate-ammonium (glufosinate), salt of glufosinate (glufosinate), glufosinate-ammonium (glufosinate), glufosinate (glufosinate), salt of glufosinate (glufosinate), glufosinate-ammonium (glufosinate), glufosinate-ammonium (salt of glufosinate), glufosinate-ammonium (glufosinate), glufosinate (glufosinate), halosulfuron-ammonium (glufosinate), glufosinate-ammonium (salt (glufosinate), halosulfuron-ammonium (salt (glufosinate), halosulfuron-ammonium (salt of glufosinate), halosulfuron-ammonium (salt (glufosinate), halosulfuron-ammonium (salt, halosulfuron-ammonium (glufosinate), halosulfuron-ammonium (salt, halosulfuron-sodium), halosulfuron-ammonium (salt, halosulfuron-sodium), halosulfuron-sodium (salt, halosulfuron-sodium), halosulfuron-sodium (salt), halosulfuron-sodium (salt), halosulfuron-sodium (salt), halosulfuron-sodium (salt, halosulfuron-sodium), halosulfuron-sodium (salt, glufosinate), halosulfuron-sodium), halosulfur, Halosulfuron-methyl (halosulfuron-methyl), halopyr (haloxydine), haloxyfop (haloxyfop), haloxyfop sodium salt (haloxyfop-sodium), esters of haloxyfop (haloxyfop-esters), haloxyfop (haloxyfop-P), esters of haloxyfop (haloxyfop-P-esters), herbimycin (herbimycin), hexachloroacetone (hexachloroacetone, HCA), hexazinone (hexazinone), imazamethabenz (imazamethabenz), imazamethamidomethyl oxalate (imazamethabenz-methyl)nz-methyl), imazapic (imazamox), imazapic ammonium salt (imazamox-ammonium), imazapic (imazapic), imazapic ammonium salt (imazapic-ammonium), imazapic (imazapyr), imazapic isopropyl ammonium (imazapyr-isopropyl), imazaquin (imazaquin), imazaquin methyl ester (imazaquin-methyl), imazaquin salt (imazin-salts), imazaquin-sodium, imazethapyr (imazethapyr), imazapic ammonium salt (imazethapyr-ammonium), imazosulfuron (imazosulfuron-methyl), indomethacin (indoxaconazole), indoxachlor (indoziflazam), ioxynil (iodofenil), iodosulfuron (methyl iodosulfuron), iodosulfuron sodium salt (iodosulfuron), iodosulfuron-methyl-iodosulfuron (iodosulfuron), iodosulfuron-methyl-sodium salt (iodosulfuron), iodosulfuron-sodium, iodosulfuron-methyl-iodosulfuron (iodosulfuron-methyl-iodosulfuron), iodosulfuron-methyl-sodium salt (iodosulfuron), iodosulfuron-methyl-iodosulfuron (iodosulfuron-methyl-sodium salt (iodosulfuron), iodosulfuron-methyl-iodosulfuron (iodosulfuron), iodosulfuron-methyl-sodium salt (iodosulfuron-methyl-iodosulfuron, iodosulfuron-methyl-iodosulfuron (iodosulfuron), iodosulfuron-methyl-iodosulfuron (iodosulfuron, iodosulfuron-methyl-iodosulfuron, iodosulfuron-methyl-iodosulfuron, iodosulfuron-methyl-ethyl-methyl-ethyl, iodosulfuron-methyl-ethyl-methyl-ethyl, iodosulfuron, iodonium, ethyl-methyl, Salts of ioxynil (ioxynil-salts), esters of ioxynil (ioxynil-esters), metrizazine (ipazone), triafamone (ipfencarbazone), propadine (iprimidim), cimetimide (isocarbamid), isofluridine (isocoryl, isoprocil), butazone (isomethazine), isoproconium (isoprocurone), isoprothiolane (isoprothiolane), isoproturon (isoproturon), isoproturon (isoprothiolane), isoprothiolane (isoprothiolane), isoprothiolane (isoprothiolane), isoprothiolane, isopLongon (isouron), isoOxamide (isoxaben), clethodim (isoxacachlorortole), isoxabenCarfentrazone-ethyl (isoxaflutole), isoxaflutoleCajeput (isoxapyrifop), tetramine (karbutilate), clenbuterol (ketospiradox), clenbuterol potassium salt (ketospiradox-potassium), lactofen (lactofen), ランコトリオン (lancotrione), ランコトリオン ナ ト リ ウ ム (lancotrione-sodium), lenacil (lenacil), linuron (linuron), MCPA, and Tributine,Salts of MCPA (MCPA-salts), esters of MCPA (MCPA-esters), MCPB, salts of MCPB (MCPB-salts), esters of MCPB (MCPB-esters), 2 methyl 4 chloropropionic acid (mecoprop, MCPP), salts of 2 methyl 4 chloropropionic acid (mecoprop-salts), esters of 2 methyl 4 chloropropionic acid (mecoprop-esters), 2 methyl 4 chloropropionic acid P (mecoprop-P), salts of 2 methyl 4 chloropropionic acid (mecoprop-P-salts), esters of 2 methyl 4 chloropropionic acid (mecoprop-P-esters), mediolate (mediloterb), medicinamide (medicinamide), medicinamide acetate (medicinamide), mefenacet (mefenacet), mefenacet (flusufide), salts of flusilamide (mesosorb-salts), ametryn (mesotrione), salts of flusilazole (mesotrione), dimerate (methazine), dimerate (methasone), salts of mesotrione (mesotrione), salts of sodium, mesotrione, salts of sodium sulfate, salts of mesotrione, salts of sodium sulfate, salts of,Metolachlor (metamifop), metamitron (metamitron), metazachlor (metazachlor), metazosulfuron (metazosulfuron), metamitron (metaflumuron), mefenpyr (metaflumuron), methabenzuron (methabenzuron), metamitron (methamphetalin), imazazole (methazole), methiocarb (methabencarb), methiuron (methauron), metoclopramide (methaprotryne), metocloprofen (methabenzuron), metamitron (methamphetamine), metamitron (methabenzuron), methimazone (methasulfofenuron), methimazone (methasulforon), metosul (metosuluron), metosul (metosul), metosul (metosuluron), metosul (metosul-methyl), metosul (metosul-methyl), metosul-methyl, metosul (metosul-methyl ), metosul-methyl, metosul (metosul-methyl, metosul, Molinate, heptanoyl ammonium, tebuconazoleCarfentrazone (monisouron), chlorsulfuron (monellinon), monosulfuron (monosulfuron), monosulfuron methyl ester (monosulfuron-methyl), meturon (CMU), and imazapyrMethyl TCA (monuron-TCA), vaaxyl (morarumquat), vaaxyl dichloride (morarumquat dichloride), napropamide (naproanilide), napropamide (napropamide), R-laevo-fenamid (napropamide-M), napropamide (napalmam, NPA), napropamide sodium salt (naptalamam-sodium), bensulfuron (neburon), nicosulfuron (nicosulfuron), fluorochlorofoam (nipyraclofon), metalaxyl (nitrolin), aclonifen (nifrofen, NIP, nilofen), trifluoromethoxyfen (nifluorofluorfen), norflurazon (norflurron), OCH, oleic acid (olenic acid), benazeron (orbetaron), pyrithiobac (anil), sulindron (meton), sulindron (sulfadiazine), sulindac (sulfaprofalin), sulindac (nitrosulfuron-M-M), napropamide (nifloran-M), napropamide (naloxonol (nifloran-M), napropamide (nifloran-N, napropamide (nifloran-M-N), napropamide (nifloran-N, napropamide(oxadiargyl) and,Oxadiazon, oxadiargyn, salts of oxadiargyn, oxasulfuron,Metribuzin (oxaziclomefone), oxyfluorfen (oxyfluorfen), paraflurron (paraflurron), paraquat (paraquat), paraquat dichloride (paraquat dichloride), paraquat dimethionate (paraquat dimethysulfonate), clenbuterol (pelbutile), pelargonic acid (nonanic acid), pendimethalin (pendimethalin), penoxsulam (penoxsulam), pentachlorophenol (pentachlorophenol), sodium pentachlorophenol (sodium pentachlorophenoxide), pentachlorophenol laurate (penuchlorophenyl laurate), mechlorethamine (penstanthanochloride, solanum, CMMP), cyclopentadien (cyclopentadienone), cloquine (paraquat chloride), and mixtures thereofClomazone (benzoxazone), fluazinam (fluazinam), pethoxamid (pethoxamid), phenprom (phenisopham), phenmedipham (phenmedipham), phenmedipham-ethyl ester (phenmedipham-ethyl), arobenzol (phenobenzuron), picloram (picloram), picloram-salts (picloram-salts), picloram-esters (picloram-e)steris), picolinafen (picolinafen), pinoxaden (pinoxaden), piperaphos (piperaphos), potassium azide (potasium azide), potassium cyanate (potasium cyanate), pretilachlor (pretilachlor), primisulfuron acid (primisulfuron), primisulfuron-methyl (primisulfuron-methyl), propineb (procyanizine), prodiamine (prodiamine), flumetsulam (profluazol), ciprofloxacin (profluorin), cycloprotodim (profoxdim), ganbaypren (proglinazine), ethyl ester of propazine (proglinazine-ethyl), prometon (prometon), prometryn (propyn, proryne), metrafron (propachloryne), propachlorfon (paprochlor), pyributicamine (paprochloride), pyributicarb (propanil), propanil (propanil),Oxalic acid (propaquizafop), propaquinone (propazine), propalaxyl (propham), propisochlor (propysochlor), propylbenzene sulfonic acid (propycarbazone), propyzamide (propyzamide), benazol (propyzazolin), prosulfuron (propyrisulfuron), propyzamide (propyzamide, propamid), methidathion (propufalin), prosulfocarb (propafecarb), prosulfuron (propyriron), prometryn (IPX), prometryn-sodium (propyzamide), propyzamide (propyzachlor), bendazol (pydanone), pyraclonil (pyrazoxynil), pyrafluazin (pyrazosulfuron), pyraflufen-ethyl (pyraflufen-ethyl), pyraflufen-ethyl (pyrazosulfuron), pyrithion-ethyl (pyrazosulfuron), pyrithion (pyrithion-ethyl), pyrithion (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyrazofen), pyriproxyfen (pyrazofen-pyriproxyfen (pyrazofen), pyriproxyfen (pyriftone (pyriproxyfen (pyriftone), pyrifturon (pyriftone), pyriftalid (pyriftalid), pyriftone (pyriftalid), pyriftone (pyriftalid), pyriftalid (pyriftalid), pyriftalid (pyriftone (pyriftalid), pyriftone (pyriftalid), pyriftalid (pyriftone (pyriftalid), pyriftalid (pyrifton (pyriftalid), pyriftalid (pyriftalid), pyrifton (pyriftalid (pyrifton (pyriftalid), pyrifton (pyriftalid), pyriftalid (pyrifton (pyrift, Pyridate (pyribac), pyriftalid (pyriftalid), pyriminobac-acid (pyriminobac), pyriminobac-methyl (pyriminobac-methyl), pyriminosulf-methyl (pyrimisulfan), pyriminosulf-acid (pyrithiobac-sodium), pyriminosulf-methyl (pyriminobac-sodium), pyroxasulfone (pyroxsulam), pyroxsulam (pyroxsulam), quinclorac (quinclorac), dimethyl ammonium quinclorac (quinclorac-dimethyl ammonium), methyl quinclorac-methyl (quinclorac-methyl), quinclorac (quinmerac), quinophthalone (quinophthalone, ACN), pyriminostrobin (quinonamide), quinamide (quinamide)Examples of suitable salts include but are not limited to but may include but are not limited to, but are also limited to, but include, but are not limited to, ethyl (quinalofop), quizalofop-esters (quinalofop-esters), quizalofop-P-esters (quizalofop-P-esters), thiocyananilides (rhodexethail), rimsulfuron (rimsulfuron), saflufenacil (saflufenacil), terbuthylazine (sibutryne), sec-buteton (secbuteton), sethoxydim (setron), siduron (simazine, CAT), simeton (simetryne), simetryn (simetryn, simetryne), sodium azide (sodiurazide), sodium chlorate (sodiumchloronate), sulcotrione (sulcotrione), esproc (sulfosulfuron), esproc (cdfalafete, sultamsultamsul), sultamsultam (sultam), sultam (s (sul), sul (s (sul-s (sul), sul (s (sul-s(s), sul (s (sul), sul (s (sul) s (sul), sul (s (sul) s (sul(s), sul (sul) s (sul (s (sul) s (sul) s), sul (s (sul), sul (s (sul) s(s) s (sul(s), sul (sul) s (sul) s(s), s (sul) s(s), sul (s (sul(s), s) s (sul (s (sul(s) s (sul(s) s (sul) s), sul (sul) s (sul(s) s (sul(s) s (sul(s), s (sul) s), s), s) s (sul, The compound is selected from the group consisting of, for example, ammonium, sulfometuron (terbutam), tebuthiuron (tebuthiorone), tefuryltrione (tefuryltrione), tembotrione (temaloxydim), terfenadine (terbacil), terbufarb (terbuterol), terbutol (MPMC), terbutrolol (terbuchlur), terbutyron (terbuteton), terbuthylazine (terbutyrazine), terbutryn (terbutryn), テトフルピロリメット (teflupentyrolme), tetraflurron (tefluuron), dimethenamid (theylchloride), thifluuron (thiazaflurazone), thiazopyr (thiazopyr), thidiazuron (thidiazuron), thifenuron (thifenuron), thifenuron (thionine (thifenuron), thifenuron (thiuron), thifenuron (トルピラレート), thifensulfuron (thiobenzofenapyr), thifensulfuron (thionine (thiobenzofenapyr), thifenuron (thionine (thiobenuron (thionine), thifenuron (thiobenuron (thionine (thifenflurazone), thifenuron (thiobenuron (thionine (thifenuron), thifenuron (thifenuron), thifenuron (thifenpyrane), thifenpyrane (thifenpyrane), thifenpyrane (thifenpyrane), thifenpyrane (thifenthiopyrane), thifenthiopyrane (thifenthiopyrane), thifenthiopyrane (thiopyrane), thifenthiopyrane (thiopyrane), thifenthiopyrane (thiopyrane), thifenthiobenzol), thifenthiobenzothiobenzothiopyrane (thiopyrane), thifenthiobenzothiobenzol (thiobenzothiobenzol), thifenthiobenzothiobenzol (thiobenzol), thifenthiobenzothiobenzol), thifenthiobenzothiobenzothiobenzothiobenzol (thiobenzothiobenzothiobenzol), thifenthiobenzothiobenzothiobenzothiobenzol), thifenthiobenzol), thifenthiobenzothiobenzol (thiobenzothiobenzol), thifenthiobenzothiobenzol (thiobenzothiobenzothiobenzothiobenzothiobenzothiobenzol), thiobenzothiobenzol), thiobenzol), thiobenzothiobenzothiobenzothiobenzothio, Triallate (triallate, tri-allolate), triasulfuron (triasulfuron), triaziflam (triaziflam), tribenuron-acid (tribenuon), tribenuron-methyl (tribenuon-methyl), dicamba (tricamba), triclopyr (triclopyr), salts of triclopyr (triclopyr-salts), esters of triclopyr (triclopyr-esters), chlorambucil (triclopyr), metribuzin (triclopyr), norflurazon (triclopyr)(trifloxysulfuron), trifloxysulfuron sodium salt (trifloxysulfuron-sodium), トリフルディモキサジン (triflumimoxadin), trifluralin (trifluralin), triflusulfuron-ic acid (triflusulfuron), triflusulfuron (triflusulfuron-methyl), トリホップ (trifop), トリホップ メ チ ル (triflop-methyl), triflusfenoxime (trifluroxime), trihydroxytriazine (trihydroxytrizine, cyanuric acid), trimetreuron (trimeturon), indene oxalyl (tripclaimed), pradacron (tritac), triflusulfuron (tritosulfuron), dichlofen (vernollate), xylazine (xylacor), ジメスルファゼット (diumzelfat), 6- { (trifluoromethyl) sulfenyl (CAS 56, N-465, N-5- (triflusulfuron) -2- (2-5-bis (diisopropylphenoxy) -2- (3-5-isopropyl-2-5-bis (Triazolyl-2-5-2-5-bis (Triazolyl-2-methyl-3, 3-5-2-5-bis (Triazolyl-methyl-2-3, 3-5-2-5-2-5-bis (diisopropylaniline, 3-5-2-5-one, 3,4, 3,4, 3,4, 3 Oxy } oxy radical]Methyl propionate (CAS 103055-25-0), propan-2-one O- (12H-dibenzo [ d, g)][1,3]Dioxacyclooctatriene-6-carbonyl) oxime (CAS503819-68-9), [ { (2- (N-methylmethylsulfonamide) -2-oxoethyl) amino } methyl]Phosphonic acid (CAS 98565-18-5), 2- [ {2- (4- ((6-chloroquinoxalin-2-yl) oxy) phenoxy) propanoyl } oxy]-ethyl 3-methyl-3-butenoate (CAS 1191932-79-2), 2- (3, 7-dichloroquinoline-8-carbonyl) -3-hydroxy-2-cyclohexen-1-one (CAS 1350901-36-8), O- (2, 4-dimethyl-6-nitrophenyl) O-methylisopropylthiophosphoramide (CAS 189517-75-7), 5- [ N- { (4, 6-dimethylpyrimidin-2-yl) carbamoyl } sulfamoyl]-1- (pyridin-2-yl) -1H-pyrazole-4-carboxylic acid methyl ester (CAS 104770-29-8), 4- [ 2-chloro-3- { (3, 5-dimethyl-1H-pyrazol-1-yl) methyl } -4- (methylsulfonyl) benzoyl]-1, 3-dimethyl-1H-pyrazol-5-yl 1, 3-dimethyl-1H-pyrazole-4-carboxylate (CAS 1911613-97-2), 4- [ 2-chloro-4- (methylsulfonyl) -3- { (2,2, 2-trifluoroethoxy) methyl } benzoyl]-1-ethyl-1H-pyrazol-5-yl 1, 3-dimethyl-1H-pyrazole-4-carboxylate (CAS 1992017-55-6), 1- { 2-chloro-3- (3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl) -6- (trifluoromethyl) phenyl } piperidin-2-one (CAS 1855929-45-1), 1, 3-dimethyl-4- {2- (methylsulfonyl) -4- (trifluoromethyl) benzoyl } -1H-pyrazol-5-yl 1, 3-dimethyl-1H-pyrazole-4-carboxylate (CAS 1622908-18-2), 2- [ {3- (2-chloro-4-fluoro-5- (3-methyl-2, 6-dioxo-4- (trifluoromethyl) -3, 6-dihydropyrimidin-1 (2H) -yl) phenoxy) pyridin-2-yl } oxy]Acetic acid BEsters (CAS 353292-31-6), 2-methyl-N- (5-methyl-1, 3,4-Oxadiazol-2-yl) -3- (methylsulfonyl) -4- (trifluoromethyl) benzamide (CAS 1400904-50-8), 2-chloro-N- (1-methyl-1H-tetrazol-5-yl) -3- (methylthio) -4- (trifluoromethyl) benzamide (CAS 1361139-71-0), 2-chloro-N- (1-methyl-1H-tetrazol-5-yl) -3- (methylsulfonyl) -4- (trifluoromethyl) benzamide (CAS1361139-73-2), 4- (4-fluorophenyl) -6- (2-hydroxy-6-oxo-1-cyclohexene-1-carbonyl) -2-methyl-1, 2, 4-triazine-3, 5(2H, 4H) -dione (CAS 1353870-34-4), F4050 (test name), F9960 (test name), OK-701 (test name), SL-1201 (test name), and the like.

A safener: benoxacor (benoxacor), bpcms (csb), cloquintocet (cloquintocet), cloquintocet-mexyl (cloquintocet-mexyl), cumyluron (cumyluron), chloranil (cyclotrinil), cyprosulfamide (cyprosulfamide), jimuron (damuron, dymron), dichlormid (dichlormid), dicyclonon (dicyclonon, diclonon), phosmet (dietholate), dimerate (dimepipe), disulfoton (disulfoton), fenchlorazole (fenchlorazole), fenchlorazole ethyl (fenchlorazole-ethyl), fenclorim (fenclorim), acetochlor (fluzole), fluxofenam (xofenam), oxaziclo (mexyl), benazol (fenflurazole)Oxazole (furilazole), ヘキシム (hexim), bisbenzeneAzoic acid (isoxadifen), bisbenzenePyrazoate (isoxadifen-ethyl), MCPA, 2-methyl-4-chloropropionic acid (mecoprop), mefenamic acid (mefenpyr), mefenpyr-diethyl, mephen-ate (mephen), メトカミフェン (methamifen), benzophenone (methoxyphenone), 1, 8-Naphthalic Anhydride (NA), octamethylenediamine (octamethylenediamine), oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5]Decane (AD67,MON4660), 4-carboxy-3, 4-dihydro-2H-1-benzopyran-4-acetic acid (CL304415), 2-dichloro-N- [ 2-oxo-2- (propenyl amino) ethyl]-N-2-propenylacetamide (DKA-24), 2- (dichloromethyl) -2-methyl-1, 3-dioxolane (MG191), 2-propenyl 1-oxa-4-azaspiro [4,5 ]]Decane-4-dithioformate (MG838), (3-dichloroacetyl-5- (2-furyl) -2, 2-dimethylOxazolidine) (MON13900), (N-allyl-N- [ (1, 3-dioxolan-2-yl) methyl]Dichloroacetamide (PPG-1292), 3- (dichloroacetyl) -2, 2-dimethyl-1, 3-Oxazolidine (R28725), 3- (dichloroacetyl) -2,2, 5-trimethyl-1, 3-Oxazolidines (R29148) and 1-dichloroacetoazepine (TI-35).

And (3) bactericide: activated ester (acibenzolar-S-methyl), octaninety-mixed acid (acibenzolar), esmolorph (aldimorph), allyl alcohol (allyl alcohol), ametoctradin (ametoctradin), アミノピリフェン (aminopyrifen), amisulbrom (amisulbactam), amobam (amobam), aminopropyl phosphonic acid (amprophyllos), trichlofen (anilazine), epoxiconazole (azaconazol), azoxycarb (azothiiram), azoxystrobin (azoxystrobin), barium polysulfide (barnium polysulphide), benalaxyl (benalaxyl-M), benalaxyl (benalaxyl), benalaxyl (benazol-M), benalaxyl (benazol), benomyl (benomyl), quinoxalone (benquinazox), propiron (benuron), fenpyrad (benthiazolirtin-S-methyl), fenpyrad (fenpyrad-ethyl), fenpyrad (biphenyl-ethyl), fenpyrad (benthiazolin), fenpyrad (bentazocarb-ethyl), fenpyrad (benthiazolin (albendan), fenpyrad (fenpyr-ethyl), fenpyrad (fenpyr-benazol-ethyl), fenpyr-benazol (benazol-ethyl), fenpyrad (benazol-benazol (benazol-benazol), benazol-benazol (benazol-ethyl), benazol-benazol (benazol-benazol (benazol-ethyl), benazol-benazol (benazol-benazol (benazol-benazol), benazol-benoxanil), benazol-benoxanil), benazol (benoxanil), benazol-benoxanil), benoxanil (benazol (benoxanil), benoxanil (benoxanil), bordeaux mixture (Bordeaux mixture), nicotinamide (boscalid), bromuconazole (bromoconazole), bupirimate (bupirimate), buthiosulphate (buthiobate), butylamine (buthylamine), lime sulphur (calcium polysulphide), dichlorvos (buthylamide)Dane (captafol), captan (captan), carbaryl (carbamorph), carbendazim (carbazazim), carboxin (carboxin), carpropamid (carpropamid), carvone (carvone), cherent mix (cheshunt mix), chlorfenapyr (chinomethionat), fenchlorazole (chlorobenhiazone), dichlofluanid (chlororaniformene), chloranil (chloronicil), benzimidazole (chlorofenazole), anisole (chloroneb), chloropicrin (chloroquine), chlorothalonil (chlorothalonil), tetrachloroquine (chloroquine), etcChlozolinox, chlozolinate, climbazole (climbazole), copper acetate (copperacetate), basic copper carbonate (basic), copper hydroxide (copperhydroxide), copper naphthenate (copperphenate), copper oleate (copperlate), copper oxychloride (copperoxolate), copper sulfate (coppersulfate), basic copper sulfate (coppersulfate, basic), copper chromate (copperzinc chromate), coumoxystrobin (coumoxystrobin), cresol (cresol), thiabendazole (cuebaneka), copper chloride (cuprobam), cyazofamid (cyazofamid), cyromazine (cyazofamid), cyflufenamide (cyazofamid (ジクロベンチアゾクス), cyflufenamide (fenpyraclostrobin (cyazofamid), cyflufenamide (fenfenamide (cyazofamid), cyflufenamide (cyazofamid (cyflufenamide (cyazofamid), cyflufenamide (cyazofamid), cyflufenamide (cyhalofenamide (cyazofamid), cyflufenamide (cyhalofenamide), cyhalofenamide (cyhalofenamide), cyhalofenamide (cyhalofenamide), cyhalofenamide (cyhalofenamide), cyhalofenamide (cyflufenamide (cyhalofenamide), cyhalofenamide (cyhalofenamide), cyhalofenamide (cyflufenamide (cyhalofenamide (cyflufenamide), cyflufenamide (cyhalofenamide), cyhalofenamide (cyflufenamide), cyhalofenamide (cyhalofenamide), cyflufenamide (cyhalofenamide), cyflufenamide), cyhalofenamide (cyflufenamide (cyhalofenamide), cyhalofenamide (cyflufenamide), cyflufenamide (cyhalofenamide (cyflufenamide (cy, Dichloronaphthoquinone (dichlone), dichlorophen (dichlorophohen), sclerotinia (dichlorzoline), diclorotriazol (diclosurazol), diclocyanide (diclocymet), pyridaben (diclomezine), niclosamide (dicloran), diethofencarb (diethofencarb), difenoconazole (difenoconazole), fluopyram (diflumetorim), dimetrimol (dimethirimol), dimethomorph (dimethomorph), dimoxystrobin (dimoxystrobin), diniconazole (diniconazole-M), dicroton (diniconazole), diniconazole ester (diniconazole), diniconazole (diniconazole), diniconazole-4 (diniconazole-4), diniconazole-6 (diniconazole-6), diniconazole (diniconazole), dinazole (octyl ester (diniconazole), dinazole (diniconazole), nitrodinazole (dinazole), nitrodinazole) nitrate (diniconazole), diniconazole) and diniconazole (dinazole), diniconazole, dinazole, diniconazole, dinazole, diniconazole, dinazole, diniconazole, dinazole, diniconazole, dinil, diniconazole, or(dinoterbon), diphenylamine (diphenylamine), ジピメチトロン (dipyrometron), pyrithion (dipyrithione), disulfiram (disulphiram), sterile phosphorus (dithimafos), dithianon (dithianon), 4, 6-dinitro-o-cresol (DNOC), dodemorph (dodemorph), dodekine (dodine), drexolone (draxolon), edifenphos (edifenphos), enestroburin (enestrobin), エノキサストロビン (enoxabin), epoxiconazole (epoxyazole), ethaboxam (ethaboxam), epoxiconazole (ethacryazole), thiophanate (ethionam), ethirimol (ethirimol), ethoxyquin (ethloxyquin), etridiazole (etridiazol),Famoxadone (fenpyroxadone), fenamidone (fenamidone), disodium diuron (fenaminosulf), fenaminostrobin (fenaminostrobin), fenapanil (fenapanil), fenaminophen (fenarimol), fenbuconazole (fenbuconazole), methylflutolanil (fenfuram), fenhexamid (fenhexamid), fenpyrad (fenpropan), fenoxanil (fenoxanil), fenpiclonil (fenpiclonil), フェンピコキサミド (fenamidod), fenpropidin (fenpropidin), fenpropimorph (fenpropamorph), fenpyrazamide (fenpyrazamide), fenpyrazamide (fenpyrazamine), fentin (fentin), ferbam (fenpyram), pyriizone (fenpyrazone), picolimide (fenpyrazoxamide), flufenamidone (flufenamidone), flufenamidone (flufenamidone), flufenamidoflufenamidone (flufenamidone), flufenamidone (flufenamidone), flufenamidoflufenamidone (flufenamidoflufenamidone), flufenamidone (flufenamidone), flufenamidone (flufenamidoflufenamidone (flufenamidone), flufenamidoflufenamidone (flufenamidone (flufenamidoflufenamidone), flufenamidone (flufenamidone), flufenamidone (flufenamidoflufenamidoflufenamidoflufenamidone), flufenamidoflufenamidone), flufenamidone (flufenamidoflufenamidone (flufenamidone), flufenamidone (flufenamidone), flufenamidoflufenamidone (flufenamidone (flufenamidoflufenamidone), flufenamidoflufenamidone (flufenamidone (flufenamidoflufenamidoflufenamidoflufenamidoflufenamidoflufenamidoflufenamidoflufenamidone (flufenamidoflufenamidoflufenamidone (flufenamidone (flufenamidoflufenamidone), flufenamidone (flufenamidone), flufenamidoflufenamidone (flufenamidone), flufenamidoflufenamidoflufenamidoflufenamidone (flufenamidone (flufenamidoflufenamidone (flufenamidone), flufenamidone (flufenamidone), flufenamidone (flu, Fluoxastrobin (fluoxastrobin), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flusulfamide (flusulfamide), flutolanil (flutolanil), fluthiacet (fluthianil), flutriafol (flutriafol), fluxapyroxad (fluxapyroxad), folpet (folpet), fosetyl-aluminum (fosetyl-aluminum), tetrachlorophthalide (fthalide), fuberidazole (fureridazole), furalaxyl (furalaxyl), furametpyr (furametpyr), difuracil (furaranil), furconazole (furconazol-cis),Fenpyroxim (furmecyclox), furametpyr (furophanate), glyodin (glyodin), griseofulvin (griseofulvin), guazatine (guazatine), quinolinylacrylate (halaricinate), hexachlorobenzene (hexachlorobenone), hexaconazole (hexaconazole), cyclohexaphos (hexythiofos), 8-hydroxyquinoline sulfate (8-hydroxyquinoline sulfate),Myclofen (hymexazol), imazalil (imazalil), imibenconazole (imibenconazole), iminoctadine-benzalkonium sulfonate (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), インピルフルキサム (immunoperfluorxam), iodopropynyl butylcarbamate (iodocarb), ipconazole (ipconazole), イプフェントリフルコナゾール (ipfentrifiunazole), イプフルフェノキン (ipflufenoquin), iprobenfos (iprobenfos), iprodione (iprodione), iprovalicarb (iprovalicarb), iprothiamide (isoflufenamid), イソフルシプラム (isofluquinacram), isothiavalicarb (isothianil), isoprothiolane (isoprothiolane), isoprothiolane (isopyrazam), imazalone (isoproturon), pyrimethanil (iprodione), pyrimethanil (isoprocarb), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione), pyrimethanil (iprodione (, Anthranilamide (mebenil), benzocarb (mecarbazid), meperflutonazole (mefenthiflunazole), mepanipyrim (mepanipyrim), mefenamidone (mepronil), meptyldinocap (meptyldinocap), metalaxyl (metalaxyl), mefenoxam (metalaxyl-M), metam (metam), metoclopramide (metazoxolone (metzoxolone), metconazole (metconazol), sulfocarb (methalostrobarb), furametocam (metfuloxaxam), メチルテトラプロール (metyltriproprole), metiram (metam), metominostrobin (metominostrobin), metrafenone (metrafenone), tiadinil (metsulfovx), metrafenone (neb), myclobutanil (myclobutanil), metsulcil (metrafenone), thiuram (metrafenone), thiuracil (metrafenone), thifluzamide (metrafin (metrafenone), thifenpyroxate (e), thiuracil (sodium), metafenim), metafenidone (metafenim), metafenicol (metafenim), thiflufenican (e (metafenican (e), thiflufenim), thiflufenican (e), thiflubensulbensulbensulbensulbensulbensulbenazol-sodium, thiuracil (e), thiuracil (thiobenazol (e), thiuracil (e), thibenazol (thiobenazol), thiuracil (e), thibenazol (e), thiuracil (thiobenazol) and (e), thibenazol (e) and (thiobenazol) and (thiobenazol) may, thifluanib), thibenazol (e) may, thibenazol (thiobenazol (e) may, thibenazol (e) may be (thiobenazol, thifluanib) may be (thiobenazol (thifluanib), thifluanib) may, thifluanib) may be (thifluani (thifluanib, thifluanib), thifluanib, thiPyrimidinol (nurimol), octhiolone (octilinone), furosemide (ofaracace), orysastrobin (orysastrobin),Oxadixyl (oxadixyl), oxathidiazuron (oxathiapigenin), oxine copper (oxine copper),Imidazole fumarate (oxyponazole fumarate), carboxin (oxypyroxin), pefurazoate (pefurazoate), penconazole (penconazol), pencycuron (pencycuron), penflufen (penflufen), pentachlorophenol (pentachlorophenonol), penthiopyrad (penthiopyrad), orthophenylol (2-phenylphenol), phosophos (phosdiphen), phthalide (phthalide), pyrazopyrad (pyraclostrobin), picoxystrobin (picoxystrobin), pyradizole (piperalin), zineb (propineb), ziram (piperacillin), ziram (phenazine), pyrimethanil (propineb), pyriproxyfen (propineb), pyriproxyfen (propicarb), pyriproxyfen (propicarb), pyrimethanil (propicarb), pyrimethan (propicarb), pyrimethan (propicarb), pyrimethan), pyrimethanil (propicarb), pyrimethan (propicarb), pyrimethan (propicarb), pyricarb (propicarb), pyrimethanil (propicarb), pyrimethan), pyricarb (propicarb), pyrimethan (propicarb), pyricarb (propicarb), pyricarb (propicarb), pyricarb (propicarb), pyricarb (propicarb), pyricarb (propicarb), pyri (propicarb), pyrim (propicarb), pyricarb (propicarb), pyrim), pyricarb), pyri (propicarb), pyri, Pyriminostrobin (pyriminostrobin), pyroquilon (pyroquilon), thionocarb (prothioconazole), prothioconazole (prothioconazole), pyraflufen (pydiflumetofen), pyraclostrobin (pyraclostrobin), ピリダクロメチル (pyraclostrobin), pyridonitrile (pyridinipyril), pyridinolone (pyridinolone), pyrimethanil (pyridinil), pyriminostrobin (pyridinifolin), pyrimethanil (pyraclostrobin)Oxazole (pyrisoxazole), pyriproxyfen (pyroxychlor), pyriproxyfen (pyroxyfur), quinate (quinatetol-sulfate), quinonebizone (quinazamid)キンコナゾール (quinconazol), phenoxyquinoline (quinoxyfen), キノフメリン (quinofumelin), quintozene (quintozene), pyrimidazole (rabenzazole), salicylanilide (salicylanilide), sedaxane (sedaxane), silthiofam (silthiofam), simeconazole (simeconazole), sodium bicarbonate (sodium hydrosylate), spiroxamine (spiroxamine), sulfur (sulfur), tebuconazole (tebuconazole), isobutoxyquinoline (tebufloquin), phylloxsulam (tecloftalam), tetrachlor (tetrachlor), thiophanate (thiophanate), thifluzamide (thiophanate), thiflufenamide (thiophanate), thifenpyrad (thiophanate), thiflufenamide (thiophanate), thifenpyrad (thiophanate), thiflufenamide (thiophanate), thifenpyr (thiophanate), thiflufenamide (thiophanate), thiflufenamide (thiophanate), thifenpyr (thiophanate (thiofenamide), thiflufenamide (thiophanate), thifenpyr (thiofenamide (thiophanate), thiflufenamide (thiofenamide), thiflufenamide (thiflufenamide), thifenpyrad-methyl), thiflufenamide (thifenpyrad-methyl), thiflufenamide (thifenpyrad-methyl, thifenpyrad-methyl thiflufenamide (thiflufenamate), thiflufenamide (thifenpyrad-methyl, thiflufenamate), thiflufenamide (thiflufenapyr-methyl, thiflufenamide (thiflufenapyr-methyl, thiflufenamate), thifenthiflufenapyr, thiflufenamide (thiflufenapyr, thiflufenamide (thiflufenamide, thiflufenapyr), thiflufenapyr, thiflufenamide (thiflufenapyr-methyl thiflufenamide, thiflufenapyr), thiflufenamide (thiflufenamide, thiflufenapyr, thiflufenamide (thiflufenamide, thiflufenapyr, thiflufenamide (thiflufenamide, thiflufenapyr, thiflufenamide, thiflufenapyr, thi, Tolylfluanid (tolyfluoride), triadimefon (triadeifen), triadimenol (triadeinol), fenvinphos (triamamphophos), pyrimethanil (triacimol), rustic acid (triazbutil), triazoxide (triazoxide), tributyltin oxide (tributyrin oxide), trichlamide (trichlamide), triclopyricarb (triclopyr), tricyclazole (tricyconazole), tridemorph (tridemorph), trifloxystrobin (trifloxystrobin), triflumizole (triflumizole), fluvalicarb (triflumizole), triforine (triforine), triticonazole (triticonazole), validamycin (validamycin), validamide (valinate), vinclozolin (fenpyrad), cyclamide (zilene), thifluzamide (thifluzamide), zinc sulfate (zinc sulfate), zinc sulfate (fenpyrad), zinc sulfate (fenpyraclostrobin (zinc sulfate), etc.

Nematocides: aldicarb (aldoxycarb), ベンクロチアズ (benclothiaz), cadusafos (cadusafos), Dibromochloropropane (DBCP), ethoprophos (dichlofenthion), Dodine (DSP), ethoprophos (ethoprophos), fenamiphos (fenamiphos), fengsulfosum (fensulfoion), triflumidine amide (fluzanolidine), diflunisone (flunsulfuron), fosthiazate (fosthiazate), thiophosphor (fosthiacetan), novalufos (imayafos), イサミドホス (isoamidofosfos), triazophos (isazofos), oxamyl (oxamyl), チオキサザフェン (thiazafen), ethoprophos (thionazin), チオキサザフェン (xadizofen) and シクロブトリフルラム (cycloflumiob), etc.

Insecticide: abamectin (abamectin), acephate (acephate), acequinocyl (acefenacyl), acetamiprid (acetamiprid), fluthrin (acrinathrin), アシノナピル (acyclonapryr), afidopyropen (afidopyropen), alfurane (aflavoraner), bollworm (alanycarb), aldicarb (aldicarb), allethrin (allethrin), alpha-cypermethrin (alpha-cypermethrin), alpha-endosulfan (alpha-osulfan), sulphaminostrobin (amidoflume), amitraz (amitraz), picolinate (picolinate), alpha-carbothion (alpha-cyhalon), alpha-carbosulfan (amidofluzine), alpha-carboxim (amitraz), and alpha-carboxim (flunixin), alpha-carboxim (amitraz)Phosphorus (azamethiphos), azinphos-ethyl, bazinpho-methyl, azocyclotin, Bacillus thuringiensis,Bendiocarb (bendiocarb), transfluthrin (benfluthrin), benfuracarb (benfuracarb), bensultap (bensultap), benfenate (benzoximate), ベンズピリモキサン (benzpyrimoxan), cyfluthrin (beta-cyfluthrin), cyhalothrin (beta-cypermethrin), bifendate (bifenazate), bifenthrin (bifenthrin), bioallethrin (bioallethrin), bioresmethrin (bioresmethrin), bistriflururon (bistrifluron), brofenflurobiluride (brofentianilide), bromopropylate (brotrophe), buprofezin (buprofezin), butocarbocarb (buticarb), carbaryl (carbaryl), carbofuran (carbofuran), carbosulfan (carbosulfan), chlorfenapyr (fenapyr), chlorfenapyr (lox), chlorfenapyr (lox (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr), chlorfenapyr (chlorfenapyr)robeziate, d-trans-propargyl thrin (chlorprophylin), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl, chromafenozide (chromafenozide), clofentezine (clofentezine), clothianidin (clothianidin), cyanophos (cycloprothons), cyantraniliprole (cyranilprol), cyromanilide (cyhalothrin), cycloprothrin (cycloprothrin), cyfluthrin (cyflumethofen), cyfluthrin (cyflumethrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cyhalothrin (cyhalothrin), cy, Dimethoate (dimethoate), methoprene (dimethylvinphos), dinotefuran (dinotefuran), benfenolan (diofenolan), ethoprophos (disulphon), 4, 6-dinitro-o-cresol (DNOC), d-T-80-tetramethrin (d-tetramethrin), emamectin benzoate (emamectin-benzoate), empenthrin (empenthrin), endosulfan (endosulfan), thiophosphine (EPN), epsilon-metofluthrin (epsilon-methofluthrin), イプシロン - モムフルオロトリン (epsilon-momfluothrin), fenpropathrin (esfenvalerate), ethiofencarb (ethiofencarb), ethofenprox (etofenprox), etofenprox (fentefuran), fentezine (fentebuconazole), fenpropiconazole (fenthion), fentefuran (fenthion), fenpropiconazole (fenthion), fentebuconazole (fenthion), fenthion (fenoxafen), fenthion (fenthion), fentebuconazole (fenthion), fenthion (fenthion), fenthion (fenthiofenthion), fenthion (fenthion), fenthiofenthion (fenthion), fenthion (fenthiofenthion), fenthion (fenthiofenthiofenthion (fenthion), fenthion (fenthion), fenthiofenthion (fenthiofenthiofenthion), fenthiofenthion (fenthion), fenthion (fenthion), fenthiofenthion (fenthion (fenthiofenthion), fenthion (fenthiofenthiofenthiofenthion (fenthiofenthion), fenthion (fenthion), fenthion (fenthiofenthiofenthion), fenthiofenthion), fenthion (fenthion), fenthiofenthiofenthiofenthion (fenthion (fenthiofenthiofenthion), fenthion (fenthion), fenthion (fenthion), fenthion (fenthiofenthion), fenthion), fenthiofenthion (fenthiofenthiofenthion), fenthion), fenthiofenthiofenthiofenthiofenthiofenthiofenthion (fenthiofenthiofenthiofenthion), fenthiofenthion (fenthion), fenthion (fenthion), fenthion (fenthion), fenthiofenthion), fenthiofenthiofenthion), fenthion (fenthiofenthion (fenthiofenthiofenthion (fenthiofenthion), fenthion (fenthion), fen, Fenpropathrin (fenpropathrin), fenpyroximate (fenpyroximate), fenthion (fenthion), fenvalerate (fenvalate), fipronil (fipronil), フロメトキン (flometoquin), flonicamid (flonicamid), fluacrypyrim (fluacrypyrim), fluazuron (fluazuron), flubendiamide (flubendiamide), flucycloxuron (flucyloxeuron), flucyanogen (flubendiamide), flubendiamide (flubendiamide), flubenconazole (flubenconazole), flubendiamide (flubendiamide), flubencarb (flubencarb), fluben (fluben-one), fluben-methyl-ethyl, ethyl-methyl-ethyl, etcPentylene (fluythrinate), pyriminostrobin (flufenerim), flufenoxuron (flufenoxuron), trifloxystrobin (flufenprox), butene-fipronil (flufiprole), フルヘキサホン (fluxafon), flumethrin (fluethrin), flupirfenidone (flupyradifurone), フルピリミン (flupyrminim), flucyanamide (fluuraner), fluvalinate (fluvalinate), フルキサメタミド (fluxamide), fonofos (thiophos), vamipramid (formamidine), thiophanate (thiophanate), furametphos (furamethocarb), lambda-cyhalothrin (gamma-cyhalothrin), benzofen (halofenprox), chlorhydrazide (halofenpyr), heptafluthrin (hexythrox), flufenoxuron (flufenuron), fenacetrin (pyrazothrin), pyrazothrin (flufenacetrin), pyraflufenacetrin (pyrazothrin), pyrazothrin (flufenoxuron), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazofenoxaflufenoxathifluthrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrazothrin (pyrazothrin), pyrafluthrin (pyrazothrin), pyraTolfenpyrad (isocycloseram), isoprofos (isofenphos), isoprocarb (isoprocarb),Triazophos (isoxathion), R-bifenthrin (kappa-bifenthrin), R-tefluthrin (kappa-tefluthrin), lambda-cyhalothrin (lambda-cyhalothrin), lepimectin (lepimectin), lufenuron (lufenuron), malathion (malathion), meperfluthrin (meperfluthrin), metaflumizone (metaflumizone), methiocarb (metaflumuron), metaldehyde (metaldehyde), methaldehyde (methamphetamine), methidathion (methidathion), methomyl (methomyl), methoprene (methomyl), methomyl (methomyl), methoxyfenozide (halothrin), methomyl (methoxyfenozide), methoxyfenozide (halothrin), methoxyfenozide (halothrin (オキサゾスルフィル), methoxyfenozide (halothrin), methoxyfenozide (halothrin), methoxyfenozide (halothrin), methoxyfenozide), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), halothrin (halothrin), chlorbenbenbenbenbenbenbenbenbenbenflurbenflurbenflurbenbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenbenbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurbenflurben, Sulfoxide phosphorus (oxydemeton-methyl), sulfoxide phosphorus (oxydeprofos), and p-sulfurPhosphorus (parathion), parathion-methyl (parathion-methyl), pentachlorophenol (pentachlorophenol), permethrin (permethrin), phenothrin (phenothrin), phenthoate (phenothrin), phorate (phorate), phorate (phosrate), phosmet (phosalon), phosmet (phosmet), phoxim (phoxim), pirimiphos (pirimiphos), Praziquantel (profenofos), proffluthrin (profluthrin), propaphos (propaphos), propargite (propaggitate), prothiofos (prothiofos), phenothrin (prothiofos), prothromazine (prothiofos), pyraflunilide (pyflumuron), pymetrozine (pyrozine), pyrazofos (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyradinil), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyriprox, Silafluofen (silafluofen), spinetoram (spinetoram), spinosad (spinosad), spirodiclofen (spirodiclofen), spirotetramat (spiromesifen), meperidine (spiroperidinofen), thioprophos (sulfoprofos), tau-fluvalinate (tau-fluvalinate), tebufenozide (tebufenozide), tebufenpyrad (tebufenpyrad), teflubenzuron (teflubenuron), tefluthrin (tefluthrin), terbufos (tefluthrin), tefluthrin (tebufenpyrazone), tefluthrin (tefluthrin), tefluthrin (tebufenpyrad), tefluthrin (tefluthrin), tefluthrin (thifenphos (tetramethrin), tefluthrin (tefluthrin), tefluthrin (thifenphos), tefluthrin (thifenphos (tefluthrin), tefluthrin (thifenphos), tefluthrin (thifenphos), tefluthrin (thifenphos), tefluthrin), thifenphos (thifenphos), tefluthrin), thifenphos), tefluthrin (thifens (thifenphos), thifenphos (thifenphos), thifenphos (thifenphos), thifenphos (thifenphos), thifens (thifenphos-methyl), thifenphos (thifenphos), thifenphos (, Triazamate (triazuron), trichlorfon (trichlorfon), triflumylpyrimidine (triflumzopyrim), triflumuron (triflumuron), チクロピラゾフロル (tyropyrazoflor), vamidothion (vamidothion), zeta-cypermethrin (zeta-cypermethrin), フルペンチオフェノックス (flupentiofenox)) And pyraclonil (cyetpyrafen), and the like.

In the composition of the present invention, a surfactant may be added as needed. Examples of these surfactants include the following (a), (B), (C), (D) and (E).

(A) Nonionic surfactant:

(A-1) polyethylene glycol type surfactant: for example, polyoxyethylene alkyl (e.g. C)_8～18) Ethers, ethylene oxide adducts of alkylnaphthols, polyoxyethylene (mono-or di-) alkyl radicals (e.g. C)_8～12) Phenyl ethers, polyoxyethylene (mono-or di) alkyl (e.g. C)_8～12) Formaldehyde condensates of phenyl ethers, polyoxyethylene (mono, di or tri) phenyl ethers, polyoxyethylene (mono, di or tri) benzyl phenyl ethers, polyoxypropylene (mono, di or tri) benzyl phenyl ethers, polyoxyethylene (mono, di or tri) styrylphenyl ethers, polyoxypropylene (mono, di or tri) styrylphenyl ethers, polymers of polyoxyethylene (mono, di or tri) styrylphenyl ethers, polyoxyethylene polyoxypropylene block polymers, alkyl groups (e.g. C)_8～18) Polyoxyethylene polyoxypropylene Block Polymer ethers, alkyl groups (e.g. C)_8～12) Phenyl polyoxyethylene polyoxypropylene Block Polymer ether, polyoxyethylene Diphenyl Ether, polyoxyethylene resin acid ester, polyoxyethylene fatty acid (e.g. C)_8～18) Monoester, polyoxyethylene fatty acid (e.g. C)_8～18) Diester, polyoxyethylene sorbitan (mono-, di-or tri-) fatty acid (e.g. C)_8～18) Esters, glycerol fatty acid ester ethylene oxide adducts, castor oil ethylene oxide adducts, hydrogenated castor oil ethylene oxide adducts, alkyl groups (e.g., C)_8～18) Amine ethylene oxide adducts and fatty acids (e.g. C)_8～18) Amide ethylene oxide adducts, and the like.

(A-2) polyol-type surfactant: for example, glycerin fatty acid ester, polyglycerin fatty acid ester, pentaerythritol fatty acid ester, sorbitol fatty acid (e.g., C)_8～18) Esters, sorbitan (mono-, di-or tri-) fatty acids (e.g. C)_8～18) Esters, sucrose fatty acid esters, polyol alkyl ethers, alkyl glycosides, alkyl polyglycosides, and fatsAlkanolamides, and the like.

(A-3) acetylene-based surfactant: for example, acetylene diols, acetylene alcohols, ethylene oxide adducts of acetylene diols, ethylene oxide adducts of acetylene alcohols, and the like.

(B) Anionic surfactant:

(B-1) carboxylic acid type surfactant: for example, polyacrylic acid, polymethacrylic acid, polymaleic anhydride, copolymers of maleic acid or maleic anhydride with olefins (e.g., isobutylene and diisobutylene, etc.), copolymers of acrylic acid with itaconic acid, copolymers of methacrylic acid with itaconic acid, copolymers of maleic acid or maleic anhydride with styrene, copolymers of acrylic acid with methacrylic acid, copolymers of acrylic acid with methyl acrylate, copolymers of acrylic acid with vinyl acetate, copolymers of acrylic acid with maleic acid or maleic anhydride, polyoxyethylene alkyl (e.g., C)_8～18) Ether acetic acid, N-methyl-fatty acid (e.g. C)_8～18) Sarcosinate, resin acids and fatty acids (e.g. C)_8～18) And the like carboxylic acids, and salts of these carboxylic acids.

(B-2) sulfate-type surfactant: for example, alkyl (e.g. C8-18) sulfates, polyoxyethylene alkyl (e.g. C)_8～18) Ether sulfates, polyoxyethylene (mono-or di) alkyl (e.g. C)_8～12) Phenyl ether sulfates, polyoxyethylene (mono-or di) alkyl (e.g. C)_8～12) Sulfuric acid esters of polymers of phenyl ethers, polyoxyethylene (mono, di, or tri) phenyl ether sulfuric acid esters, polyoxyethylene (mono, di, or tri) benzyl phenyl ether sulfuric acid esters, polyoxyethylene (mono, di, or tri) styryl phenyl ether sulfuric acid esters, sulfuric acid esters of polymers of polyoxyethylene (mono, di, or tri) styryl phenyl ethers, sulfuric acid esters of polyoxyethylene polyoxypropylene block polymers, sulfated oils, sulfated fatty acid esters, sulfated fatty acids, sulfated olefins, and the like, and salts of these sulfuric acid esters.

(B-3) sulfonic acid type surfactant: for example, paraffins (e.g. C)_8～22) Sulfonic acids, alkyl radicals (e.g. C)_8～12) Benzenesulfonic acids, alkyl radicals (e.g. C)_8～12) Formaldehyde condensates of benzenesulfonic acid, formaldehyde condensates of cresolsulfonic acid, alpha-olefins (e.g. C)_8～16) Sulfonic acids, dialkyl radicals (e.g. C)_8～12) Sulfosuccinic acid, lignosulfonic acid, polyoxyethylene (mono-or di) alkyl (e.g. C)_8～12) Phenyl Ether sulfonic acid, Polyoxyethylene alkyl (e.g. C)_8～18) Ether sulfosuccinic acid half-esters, naphthalenesulfonic acids, (mono-or di) alkyl (e.g. C)_1～6) Naphthalenesulfonic acid, formaldehyde condensates of naphthalenesulfonic acid, (mono-or di-) alkyl (e.g. C)_1～6) Formaldehyde condensates of naphthalenesulfonic acids, of creosote sulfonic acids, alkyl radicals (e.g. C)_8～12) Diphenyl ether disulfonic acid, イゲポン T (trade name), sulfonic acids such as polystyrene sulfonic acid and a copolymer of styrene sulfonic acid and methacrylic acid, and salts of these sulfonic acids.

(B-4) phosphate ester type surfactant: for example, alkyl (e.g. C)_8～12) Phosphoric acid esters, polyoxyethylene alkyl (e.g. C)_8～18) Ether phosphates, polyoxyethylene (mono-or di) alkyl (e.g. C)_8～12) Phenyl ether phosphates, polyoxyethylene (mono-, di-or tri) alkyl (e.g. C)_8～12) Phosphoric acid esters of phenyl ether polymers, polyoxyethylene (mono, di, or tri) phenyl ether phosphoric acid esters, polyoxyethylene (mono, di, or tri) benzyl phenyl ether phosphoric acid esters, polyoxyethylene (mono, di, or tri) styryl phenyl ether phosphoric acid esters, phosphoric acid esters of polyoxyethylene (mono, di, or tri) styryl phenyl ether polymers, phosphoric acid esters of polyoxyethylene polyoxypropylene block polymers, phosphoric acid esters of phosphatidylcholine, phosphatidylethanolamine, condensed phosphoric acid (e.g., tripolyphosphate), and the like, and salts of these phosphoric acid esters.

Examples of the counter ion of the salt in the above-mentioned (B-1) to (B-4) include alkali metals (lithium, sodium, potassium, etc.), alkaline earth metals (calcium, magnesium, etc.), ammonium, and various amines (for example, alkylamine, cycloalkylamine, alkanolamine, etc.).

(C) Cationic surfactant:

for example, alkylamine, alkyl quaternary ammonium salt, ethylene oxide adduct of alkylamine, ethylene oxide adduct of alkyl quaternary ammonium salt and the like.

(D) Amphoteric surfactant:

(D-1) betaine type surfactant: examples thereof include, for example, alkyl (e.g., C)_8～18) Dimethylaminoacetic acid betaines, acyl radicals (e.g. C)_8～18) Aminopropyl dimethyl aminoacetic acid betaine, alkyl (e.g. C)_8～18) Hydroxysultaines and 2-alkyl radicals (e.g. C)_8～18) -N-carboxymethyl-N-hydroxyethyl imidazolineBetaine.

(D-2) amino acid type surfactant: examples thereof include, for example, alkyl (e.g., C)_8～18) Aminopropionic acids, alkyl radicals (e.g. C)_8～18) Aminodipropionic acid and N-acyl radicals (e.g. C)_8～18) -N '-carboxyethyl-N' -hydroxyethylethylenediamine.

(D-3) amine oxide type surfactant: examples thereof include, for example, alkyl (e.g., C)_8～18) Dimethylamine oxides and acyl radicals (e.g. C)_8～18) Aminopropyl dimethylamine oxide, and the like.

(E) Other surfactants:

(E-1) silicon-based surfactant: examples thereof include polyoxyethylene/methylpolysiloxane copolymers, polyoxypropylene/methylpolysiloxane copolymers and poly (oxyethylene/oxypropylene)/methylpolysiloxane copolymers.

(E-2) fluorine-based surfactant: examples thereof include perfluoroalkylbenzenesulfonates, perfluoroalkylsulfonates, perfluoroalkyl carboxylates, perfluoroalkylpolyoxyethylene ethers, perfluoroalkyl polyoxyethylene ethers, and perfluoroalkyl trimethylammonium salts.

These surfactants may be used alone or in combination of 2 or more, and the ratio in the case of mixing may be freely selected. The content of the surfactant in the composition of the present invention may be appropriately selected, but is preferably in the range of 0.1 to 20 parts by weight based on 100 parts by weight of the composition of the present invention.

The composition of the present invention may further contain various adjuvants. Examples of the auxiliary agents that can be used include thickeners, organic solvents, antifreezes, antifoaming agents, antifungal agents, and coloring agents, and the following are mentioned.

The thickener is not particularly limited, and organic and inorganic natural products, synthetic products and semi-synthetic products can be used, and examples thereof include heteropolysaccharides such as xanthan gum (xanthan gum), welan gum and neutral gum, water-soluble high molecular compounds such as polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, sodium polyacrylate and polyacrylamide, cellulose derivatives such as methyl cellulose, carboxymethyl cellulose, carboxyethyl cellulose, hydroxyethyl cellulose and hydroxypropyl cellulose, and smectite clay minerals such as montmorillonite, saponite, hectorite, bentonite, laponite and laponite. These thickeners may be used in 1 kind or mixed in 2 or more kinds, and the ratio in the case of mixing may be freely selected. These thickeners may be added as they are, or may be added in the form of a material dispersed in water in advance. Furthermore, the content in the composition of the present invention can also be freely selected.

Examples of the organic solvent include alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and isopropyl alcohol, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as γ -butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, aromatic hydrocarbons such as xylene, alkylbenzene, phenylxylylethane, and alkylnaphthalene, mechanical oils, aliphatic hydrocarbons such as N-paraffin, isoparaffin, and cycloparaffin, mixtures of aromatic hydrocarbons such as kerosene and aliphatic hydrocarbons, and oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, and castor oil.

As antifreeze agents, for example, ethylene glycol, diethylene glycol and propylene glycol, glycerol and the like can be used. Propylene glycol and glycerin are preferred. Furthermore, the content in the composition of the present invention can also be freely selected.

Further, defoaming agents such as silicone emulsions, antibacterial and antifungal agents, coloring agents, and the like can be blended.

The method for producing the composition of the present invention is not particularly limited, and the composition can be obtained by adding the above-mentioned components to a dispersion medium and mixing them with a stirrer. Further, the pesticidal active ingredient, the surfactant and other adjuvants may be finely pulverized by a dry-type pulverizer and a wet-type pulverizer, either individually or in combination, as required.

The dry pulverization can be carried out by a hammer mill, a pin mill, a jet mill, a ball mill, a roll mill or the like. The fine pulverization by wet pulverization can be carried out by a wet pulverizer such as an in-line mill or a bead mill.

The composition of the present invention can be used as a herbicide for paddy fields in any of the methods of soil treatment and foliage treatment under irrigation (Japanese: flood). Preferably, it can be used in a treatment method using stem and leaf treatment. Examples of paddy field weeds include those represented by the moleplant (Chinese sprinage, Leptochloa chinensis), the moleplant (bearded spatgletop, Leptochloa fascicularis), barnyard grass (barnyard grass, Echinochloa crus-galli), barnyard grass (junglerice, Echinochloa colonum), barnyard grass (late watering grass, Echinochloa oryzicola), Leptochloa grass (southern grass, Leersia hexandra), Paspalum bicolor (Knotgrass, Paspalum paniculatum), field platypodium (Saramonia paniculata, Ishium paniculatum), Cyanophora cylindrical grass (triticum paniculatum), Graphyceae grass (rice paniculate grass), Gracilaria japonica, Graves (indica), Graves grass (sorghum paniculata), Graves (Graves), Graves (rice grass), Graves (sorghum paniculatum), Graves (rice grass), rice grass, Fimbristylis miliacea, Iris lactuca (Japanese white rush, Schizophyllum juncoides), Cyperus trifoliatus (Schizophyllus nipponicus), Cyperus chinensis (Cyperus rotundus), Cyperus rotundus (Schizophyllus communis), Cyperus rotundus (Cyperus serotinas), Cyperus rotundus (Smallanthus sonchifolius), Cyperus rotundus (Cyperus sempervirens (Smilaxus sempervirens), Cyperus brevicaulis (Cyperus sempervirens), Cyperus rotundus (Cyperus nutgrass, Cyperus rotundus), Cyperus nutgrass (Cyperus indicus, Cyperus perus), and Sparganium vulus crispus (Sargassaceae, Saakkura, Samalus chinensis, and the like), and Morchella indica (Moraceae), Moraceae, Morus chinensis (Morinaceae, Morus indica, Morinaceae, and the, Monochoria vagiana, Verbascum (Heteranthera limacina), and Eichhornia crassipes (Water hyacinths, Eichhornia crassipes) as representative of the Racanidae (Ponteriaceae) weeds, Verbenaceae (Eltinaceae) weeds as representative of the triple-pistil (Thamese waterstem, Elatine triandra) and the like, Amaranthus longifolia (redstem, Ammannia coccinea) as representative of the triple-pistil, and Arthropoda japonica (Indian. benthamiana) as representative of the triple-muff, Rotala indica as representative of the Veratridae (Lythraceae) weeds, Salicis (Ludwigia indica) as representative of the Veronica and the Veronica officinalis (Linteobacilaria officinalis), and Veronica (Linteobacilaria officinalis), Lippia japonica (Linteum nigriperidae) as representative of the Veronica officinalis, Veronica officinalis) as representative of the Veronica officinalis, Veronica indica (Linteobacilaria officinalis) as representative of the Veronica indica, Veronica indica (Valeriana officinalis) as the family, Veronica indica (Linteobacilaria officinalis), and the Veronica indica (Linteobacilaria officinalis) as representative of the Veronica), and the Verbenaria officinalis (Linteobacilaria officinalis, Linteobacilaria japonica, and the Verbenaria japonica, Linteobacilaria japonica, Linipes (Linipecacalia, and the Verbenaria officinalis, Linteobacilaria officinalis, and the Eichia indica, the Eichia indica (Linteobacilaria officinalis) as the extract of the family of the Eichia indica, the Verbenaria officinalis, the family of the family, Amaranthaceae (Amaranthaceae) weeds represented by Alternanthera philoxeroides, Amaranthus spinosus, Amaranthus spinosus, Polygonaceae (water pepper, Polygonum hydropiper) and the like, spiraceae (sphaecales) weeds represented by spiraea japonica, Sphenothecaceae (sphaerotheca) and the like, Fabaceae (Fabaceae) weeds represented by Aeruginea, achynomene indica, Sesbania sessilifolia, Sesbania seganica and the like, pennisetum vulgare (wolfsberi) weeds represented by pennisetum, Agastache rugosa, Sesbania segalanta, Sesbania exaltata and the like, pennisetum vulgare (wolfsberi) weeds represented by pennisetum' grasses, Bitteraria japonica, pennisetum parthenocauliflora, pennisetum americana, pennisetum partnerium sativum, pennisetum americana and the like, Asteraceae (araliaceae) weeds represented by Marsileaceae, Echinacea and the like, and the like, And Lemnaceae (lemnae) weeds typified by duckweed (Lemna paucicostata), and ophthalmonaceae (Potamogetonaceae) weeds typified by gynura pombe (rodleaf pondweed, Potamogeton distentis).

The composition of the present invention is useful as a herbicide for upland and orchard, and can be used in any of soil treatment, soil mixing treatment and foliage treatment. Examples of upland field weeds include those selected from the group consisting of wild millet (wild Panicum, Panicum dichotomiforum), wild Sorghum (shattercane, Sorgham bicolor), carex (johnson grass, Sorghum halepense), barnyard grass (barnyard grass, ecochloa cruris-galli), Phalaris (cocksper grass, ecochloa cruris-galli), Echinochloa crassa (cockochloa crura, Echinochloa cruris-galli var. pratica), Echinochloa cruris (japanese barnyard, Echinochloa cois), Digitaria crassa (southern craving, Digitaria ciliata), Digitaria auriculata (Digitaria auricularia auricula), Digitaria auricula, Digitaria auriculata (Digitaria auriculata), Sorghum, Digitaria auriculata, Sorghum, Poa annua), goosegrass (goose grass, Eleusine indica), green foxtail (green foxtail, Setaria virilia), big green foxtail (giant foxtail, Setaria faberi), signalized grass (signalgrass, Brachiaria decumbens), and tribulus terrestris (southern sandbur, Cenchrus echiana) and the like, Cyperaceae (Cyperaceae) weeds represented by Cyperus rotundus and the like, Solanum nigrum (black belly, Solanum nigrum), and Datura stramonium(fungal weed, Amaranthus roseus, Amaranthus rose, Matricaria matricarioides), achyranthes aspera (Galinsoga, Cirsium villosa), Silybum marianum (canada thistle, Cirsium arvense), Senecio vulgaris (common grounese, Senecio vulgaris), and Elaeis annua (annual fleabane, Erigeron annua), and the like, Compositae (Asteraceae), Indian (greengrocery, Rorippa indica), Arabidopsis thaliana (wild musta, Sinapis arvensis), and camelina sativa (shepherd)_’Cruciferae (Brassicaceae) weeds represented by s pull, Capsella bursa-pastoris, etc., Polygonaceae (Polygonaceae) weeds represented by Polygonum longiradiatum (oriented lady's tuber, Persicaria longiseta), and Polygonaceae (Polygonaceae) weeds represented by Polygonum convolvulus (Polygonum convolvulus), Portulaca oleraceae (Portulacaceae) weeds represented by Portulaca oleracea, etc., quinoa (lambsquarquaters, Chenopodium album), Chenopodium quinoa (fifth gordonia gooseefoot, Chenopodium fistulosum), Kochia scoparia, and Chenopodium album (moisture, etc.), Chenopodium quinoa (Salacia, bamboo) represented by Chenopodium villosa, etcThe weeds of plantago (Plantaginaceae) represented by alabastrum (persian speedwell, Veronica persica) and the like, the weeds of Commelinaceae (Commelinaceae, Commelina communis) represented by Commelina (asiatic dayflower, Commelina communis) and rice grass (benghal dayflower, Commelina benghalensis) and the like, the weeds of Lamiaceae (Lamiaceae) represented by lapis (lanuca), the weeds of lamiophytum (lamiophytum, Lamium amplexicaule) represented by lamiophytum (purple detangle, Lamium purpureum) and the like, the weeds of lamiophytum (lamiophytum, Euphorbia maculata) and the weeds of pachydermata (wild spipe, Euphorbia), the weeds of Euphorbiaceae (lilac), the weeds of rubus (purpurea), the weeds of rubus and the plants of rubus (purpurea), the weeds of the family Rubiaceae (purpurea), the plants (purpurea), the weeds of the plants of the family Sesbania exaltata), legume (Fabaceae) weeds typified by senecio (Cassia obtusifolia ) and the like, and Oxalis (Oxalidaceae) weeds typified by creeping woodsorrel (Oxalis corniculata) and the like.

Further, the composition of the present invention can weed a wide range of weeds which are generated in, for example, a non-agricultural land requiring control of the growth of weeds, such as an industrial facility land including a slope surface of a dam, a river land, a road shoulder and a slope surface, a railway land, a park green land, a sports field, a parking lot, an airport, a work site, a storage facility and the like, a fallow land, an idle land in an urban area and the like, or a fruit garden land, a pasture land, a lawn land, a forestry land and the like. Examples of the weeds include, in addition to those described for weeds in upland and orchard, bluegrass (annual bluegrass, Poa annua), dandelion (dandelion, Taraxacum officinale), sweetclover (hair cream, Conyza bonariensis), eriensis canadensis (horseweeed, Conyza canadensis), thauma surname (guenthe white wine, Conyza sumatriensis), Cardamine flexneri (road bit, Cardamine flexuosa), white clover (white clover, Trifolium repens), coriander (lawn pennywort), centipede (centipede ), and the like.

The composition of the present invention can control the growth of plants which are not desired for useful plants by acting on the useful plants, or on the locus where the useful plants are intended to grow or have grown, or on non-agricultural lands, simultaneously or separately. The above-mentioned useful plants include dry crops, paddy field crops, horticultural crops, grasses, fruit trees and the like.

In the present invention, specific examples of useful plants include crops such as corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, and tobacco; solanaceous vegetables (eggplant, tomato, sweet pepper, hot pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, mustard, broccoli, cauliflower, etc.), compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), liliaceae vegetables (onion, garlic, asparagus, etc.), umbelliferae vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceae vegetables (spinach, beet, etc.), labiatae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, japanese yam, taro, etc.; pomes (apple, pear, japanese pear, chinese quince, etc.), stone fruits (peach, plum, nectarine, plum, prunus cerasus, apricot, prunus humilis, etc.), citrus (satsuma mandarin, sweet orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (cowberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, loquat, banana, coffee, date palm, coconut, oil palm, etc.; tea, mulberry, street tree (ash, birch, dahlia, eucalyptus, ginkgo, syringa, maple, oak, poplar, cercis, maple, sycamore, zelkova, japanese cedar, japanese fir, japanese hemlock, juniper, pine, spruce, yew, elm, horse chestnut, etc.), coral tree, Japanese cedar, Japanese cypress, Japanese metaphylium, Japanese winged euonymus, photinia glabra, etc., trees other than fruit trees; lawns such as zoysia (zoysia japonica, zoysia sulcata, etc.), cibot roots (bermudagrass, etc.), glume-grass (giant glume-grass, siberian glume-grass, thin glume-grass, etc.), poaceae (meadow grass, common poa, etc.), fescue (festuca arundinacea, fine fescue, etc.), secale grass (ryegrass, etc.), dactylicao, timothy grass, etc.; oil palm, jatropha and other oil and grain crops; flowers (roses, carnations, chrysanthemums, eustoma grandiflorum, hamamelis, flint flowers, marigold, sage, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily, lavender, violet, kale, primula, poinsettia, gladiolus, cattail, marguerite, vervain, cymbidium, beggarland, etc.); foliage plants, but are not limited thereto.

The composition of the present invention can be applied by, for example, diluting the composition with a stock solution or water to about 50 to 5000 times, and spraying the diluted composition on crops, trees, or soil where the trees grow on the diluted composition with a sprayer or the like; diluted to about 2 to 100 times with a stock solution or water, and applied by spraying from the air using a helicopter or the like.

The composition of the present invention is excellent in, for example, storage stability, flowability, herbicidal effect and the like of the uncured compound (1) in the composition, when compared with a composition comprising an amorphous compound (1). In particular, the present invention is more remarkable in the case where the composition is in the form of a suspension or an aqueous suspension.

Examples

The present invention will be described in further detail below by specifically describing production examples of the crystal of the present invention as examples, but the present invention is not limited thereto.

The various measurement conditions are as follows.

[ conditions for measuring powder X-ray diffraction ]

The device comprises the following steps: x' PERT-PRO MPD (スペクトリス Kabushiki Kaisha)

The determination method comprises the following steps: transmission method

X-ray: Cu-K alpha

Voltage: 45kV

Current: 40mA

Sampling interval: 0.0070deg

Data range: 2 theta 5 to 40deg

[ differential scanning calorimetry measurement conditions ]

The device comprises the following steps: DSC-60 (manufactured by Shimadzu Kagaku Co., Ltd.)

And (3) heating: 20 deg.C- (10 deg.C/min) -450 deg.C

Atmosphere: nitrogen gas

Comparison: al (Al)₂O₃

A container: SUS-made products

Sampling: 1 second

[ production example 1 ]: production of crystals of the present invention 1

In 3- [ (isopropylsulfonyl) methyl]-5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]To a mixed solution of 34.83g of pyridine-8-carboxylic acid and 348.30g of 1, 2-dichloroethane were added 14.90g of thionyl chloride under heating reflux. After the end of the addition, the reaction mixture was stirred under heating reflux for 4.5 hours. After completion of the stirring, 80.62g of the solvent was distilled off at 60 ℃ under reduced pressure. After the completion of the distillation, 5-methyl-1, 3,4-9.83g of diazole-2-amine and 174.20g of 1, 2-dichloroethane. After the end of the addition, 179.00g of the solvent of the reaction mixture was distilled off under reduced pressure at 60 ℃. After completion of the distillation, 175.00g of 1, 2-dichloroethane, 2.51g of potassium acetate and 175.00g of water were added at 60 ℃ to separate the mixture. The resulting aqueous layer was extracted with 175.00g of 1, 2-dichloroethane. The organic layer thus obtained was washed with water, and 307.45g of the solvent was distilled off at 70 ℃ under reduced pressure. After completion of the distillation, 1, 4-bis (tert-butyl) was added to the resulting slurry at 70 ℃209.00g of alkyl. After the end of the addition, the resulting slurry was cooled down to-2 ℃ at a cooling rate of 1 hour at 25 ℃ whereAfter stirring at temperature for 1 hour, filtration was performed. The obtained crystals were washed with 105.00g of ethyl acetate at 0 ℃ and then dried under reduced pressure, whereby 31.40g of the crystals of the objective substance were obtained.

The powder X-ray diffraction of the obtained crystal was measured, and the diffraction pattern of fig. 1 was shown.

Further, the obtained crystal was subjected to differential scanning calorimetry, and the peak pattern of fig. 2 was shown.

[ production example 2 ]: production of crystals of the present invention 2

In 3- [ (isopropylsulfonyl) methyl]-5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]To a mixed solution of 9.93g of pyridine-8-carboxylic acid and 99.3g of 1, 2-dichloroethane, 4.10g of thionyl chloride was added under heating and refluxing. After the end of the addition, the reaction mixture was stirred under heating under reflux for 4 hours. After completion of the stirring, 20.5g of the solvent was distilled off under reduced pressure at 60 ℃. After the completion of the distillation, 5-methyl-1, 3,4-2.80g of diazole-2-amine and 49.7g of 1, 2-dichloroethane. After the end of the addition, 66.5g of the solvent of the reaction mixture was distilled off under reduced pressure at 60 ℃. After completion of the distillation, 66.5g of 1, 2-dichloroethane was added at 60 ℃. After the end of the addition, 56.6g of the solvent of the reaction mixture was distilled off under reduced pressure at 60 ℃. After completion of the removal by distillation, 56.6g of 1, 2-dichloroethane, 0.69g of potassium acetate and 44.7g of water were added thereto at 60 ℃ to separate the mixture. The resulting aqueous layer was extracted with 39.7g of 1, 2-dichloroethane. The organic layer thus obtained was washed with water, and 69.5g of the solvent was distilled off at 60 ℃ under reduced pressure. After completion of the distillation, 9.93g of N, N-dimethylformamide was added to the resulting slurry at 60 ℃. After the addition was completed, the mixed solution was stirred at 85 ℃ to dissolve the crystals. The mixed solution was cooled to 60 ℃, and 5mg of a seed crystal of the target substance (crystal using the target substance obtained in production example 1) was added while stirring. After the completion of the addition, the mixture was stirred at 60 ℃ and the precipitation of crystals was visually confirmed, followed by cooling at 30 ℃ for 1 hourThe cooling rate was increased to-2 ℃. The resulting slurry was stirred at-2 ℃ for 3 hours, and then filtered. The obtained crystals were washed with 9.93g of 1, 2-dichloroethane at 0 ℃ and then dried under reduced pressure, whereby 9.51g of crystals of the objective substance was obtained.

The powder X-ray diffraction of the obtained crystal was measured, and the diffraction pattern of fig. 1 was shown.

Further, the obtained crystal was subjected to differential scanning calorimetry, and the peak pattern of fig. 2 was shown.

[ production example 3 ]: production of crystals of the present invention 3

Step 1: synthesis of 3- [ (isopropylsulfonyl) methyl ] -5- (trifluoromethyl) - [1,2,4] triazolo [4,3-a ] pyridine-8-carbonyl chloride

To a mixed solution of 1.00g of 3- [ (isopropylsulfonyl) methyl ] -5- (trifluoromethyl) - [1,2,4] triazolo [4,3-a ] pyridine-8-carboxylic acid and 10g of toluene was added 0.43g of thionyl chloride under heating and refluxing. After the end of the addition, the reaction mixture was stirred under heating under reflux for 1 hour. After completion of the stirring, the solvent was distilled off under reduced pressure, whereby 1.10g of the objective substance was obtained as a pale brown solid.

Melting point: 140-142 deg.C

And a step 2: production of crystals of the invention

In 3- [ (isopropylsulfonyl) methyl]-5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]5-methyl-1, 3, 4-pyridine-8-carbonyl chloride (1.10 g) and toluene (10 g) are added to a mixed solution at room temperature0.285g of diazole-2-amine. After the end of the addition, the reaction mixture was stirred under heating reflux for 2 hours. After the stirring was completed, the reaction mixture was cooled to room temperature. The resulting slurry was stirred at room temperature for 1 hour, and then filtered. The obtained crystals were washed with 5.0g of toluene at room temperature and then dried under reduced pressure, whereby 1.00g of crystals of the objective substance was obtained.

The powder X-ray diffraction of the obtained crystal was measured, and the diffraction pattern of fig. 1 was shown.

[ production example 4 ]: production of crystals of the present invention 4

Step 1: synthesis of 3- [ (isopropylsulfonyl) methyl ] -5- (trifluoromethyl) - [1,2,4] triazolo [4,3-a ] pyridine-8-carbonyl chloride

To a mixed solution of 1.00g of 3- [ (isopropylsulfonyl) methyl ] -5- (trifluoromethyl) - [1,2,4] triazolo [4,3-a ] pyridine-8-carboxylic acid and 10g of 1, 2-dichloroethane was added 0.43g of thionyl chloride under heating and refluxing. After the end of the addition, the reaction mixture was stirred under heating under reflux for 4 hours. After completion of the stirring, the solvent was distilled off under reduced pressure, whereby 1.08g of the objective substance was obtained as a pale brown solid.

And a step 2: production of crystals of the invention

In 3- [ (isopropylsulfonyl) methyl]-5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]5-methyl-1, 3, 4-pyridine-8-formyl chloride (1.08 g) and 1, 2-dichloroethane (10 g) were added to a mixed solution at room temperature0.285g of diazole-2-amine. After the end of the addition, the reaction mixture was stirred under heating reflux for 3 hours. After the stirring was completed, the reaction mixture was cooled to room temperature. The resulting slurry was stirred at room temperature for 1 hour, and then filtered. The obtained crystals were washed with 3.0g of 1, 2-dichloroethane at room temperature and then dried under reduced pressure, whereby 0.484g of crystals of the objective substance was obtained.

The powder X-ray diffraction of the obtained crystal was measured, and the diffraction pattern of fig. 1 was shown.

[ reference example 1 ]: production of an amorphous compound (1) was carried out according to the description of synthetic example 2 in example of International publication No. 2014/192936.

In 3- [ (isopropylsulfonyl) methyl]-5- (trifluoromethyl) - [1,2,4]Triazolo [4,3-a]Pyridine-8-carboxylic acid 200mg, 5-methyl-1, 3,4-67.8mg of diazol-2-amine and 5ml of N, N-dimethylformamide were added to a mixed solution at room temperature, 1-ethyl-3- (3)-dimethylaminopropyl) carbodiimide hydrochloride 131.1mg and 1-hydroxy-7-azabenzotriazole 93.2 mg. After the end of the addition, the reaction mixture was stirred at room temperature for 24 hours. After completion of the stirring, water was added to stop the reaction, and the mixture was extracted with chloroform (10ml × 1 times). After the obtained organic layer was washed with water, it was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography { n-hexane: ethyl acetate: methanol 50: 50: 0 to 0: 100: 0 to 0: 80: 20 (volume ratio) } purification to obtain 204.4mg of an amorphous substance of compound (1).

The powder X-ray diffraction of the resulting amorphous body was measured, and the diffraction pattern of FIG. 3 was shown.

In addition, differential scanning calorimetry measurement of the obtained amorphous body was performed, and the result showed the peak pattern of fig. 4.

Industrial applicability

According to the present invention, crystals of the compound (1) can be produced.