Trifluoromethanesulfonanilide compound and method for producing same

Abstract

The present invention relates to: a trifluoromethanesulfoninanilide compound represented by formula (1) (In the formula, M represents a hydrogen atom or a C1-C6 alkyl.); and a method for producing the same.

Description

Trifluoromethanesulfon anilide compounds and methods for producing the same

[0001] This invention relates to a novel trifluoromethanesulfonanilide compound or a salt thereof, and a method for producing the same. Furthermore, this invention relates to a method for producing the reduction product of the said trifluoromethanesulfonanilide compound or salt thereof.

[0002] For example, Patent Documents 1 and 2 disclose certain trifluoromethanesulfonanilide compounds, but they do not disclose anything about the trifluoromethanesulfonanilide compound according to the present invention, its manufacturing method, or a novel method for producing the reduction product of said trifluoromethanesulfonanilide compound. Furthermore, Patent Documents 3 and 4 disclose a method for producing a compound that has a structure similar to the reduction product of said trifluoromethanesulfonanilide compound.

[0003] International Publication No. 2014 / 046244, International Publication No. 2015 / 060402, International Publication No. 2009 / 049165, International Publication No. 2009 / 049157

[0004] The object of the present invention is to provide a novel trifluoromethanesulfonanilide compound or a salt thereof, a method for producing the same, and a novel method for producing its reduction product.

[0005] The present inventors, through diligent research aimed at solving the above-mentioned problems, have discovered a novel trifluoromethanesulfonanilide compound or a salt thereof represented by the following formula (1), a method for producing the same, and a novel method for producing its reduction product, thereby completing the present invention.

[0006] An embodiment of the present invention is given by formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ It is a trifluoromethanesulfon anilide compound or a salt thereof, represented by [] which represents alkyl.

[0007] A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to an embodiment of the present invention is given by formula (2): A compound represented by or a salt thereof is dissolved in a solvent with hydroxylamine or C１ ~C ６ When reacted with an alkoxyamine having an alkoxy group, formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A trifluoromethanesulfon anilide compound or a salt thereof, represented by [representing alkyl], is produced.

[0008] A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to one embodiment of the present invention is given by formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A trifluoromethanesulfonanilide compound represented by [representing alkyl] or a salt thereof is reduced in a hydrogen atmosphere in the presence of a catalyst to obtain formula (3): A trifluoromethanesulfon anilide compound represented by or a salt thereof is produced.

[0009] A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to another embodiment of the present invention is given by formula (2): The compound represented by is reacted with ammonia in the presence of a catalyst containing at least one of Raney nickel, palladium, and platinum, and the resulting reaction product is further reduced in a hydrogen atmosphere to obtain formula (3): A trifluoromethanesulfon anilide compound represented by or a salt thereof is produced.

[0010] According to the present invention, it is possible to provide novel trifluoromethanesulfonanilide compounds or salts thereof, methods for producing the same, and novel methods for producing the reduction products thereof.

[0011] Embodiments of the present invention will be described in detail below. However, the scope of the present invention is not limited to the specific examples described below. Furthermore, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits.

[0012] In the compound represented by formula (1) (hereinafter also referred to as "the compound of the present invention (1)") or a salt thereof, the existence of tautomers is conceivable, and the compound of the present invention (1) includes all tautomers or a mixture of tautomers contained in any ratio.

[0013] Formula (1): [In the formula, M represents a hydrogen atom or C １ ~C ６ alkyl. ]

[0014] In the compound of the present invention (1), geometric isomers of the E-form and Z-form may exist, and the compound of the present invention (1) includes these E-form, Z-form or a mixture containing the E-form and Z-form in any ratio.

[0015] Further, in the compound of the present invention (1), an optically active form may exist due to the presence of one or more asymmetric carbon atoms, and the compound of the present invention (1) includes all optically active forms or a racemate.

[0016] Also, in the compound of the present invention (1), tautomers may exist depending on the type of substituent, and the compound of the present invention (1) includes all tautomers or a mixture of tautomers contained in any ratio.

[0017] Also, the compound of the present invention (1) may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, and the compound of the present invention (1) includes all rotational isomers or a mixture of diastereomers contained in any ratio.

[0018] Among the compounds (1) of the present invention, those that can be made into salts by conventional methods include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; salts of aluminum; and quaternary ammonium salts such as tetramethylammonium salt, tetrabutylammonium salt, and benzyltrimethylammonium salt.

[0019] Compound (1) of the present invention has excellent herbicidal effects against various weeds. Furthermore, it has excellent mycelial growth inhibitory activity against various pathogenic fungi. Therefore, compound (1) of the present invention can provide a novel trifluoromethanesulfonanilide compound or a salt thereof that is useful as a herbicide and fungicide.

[0020] Next, specific examples of each substituent shown in this specification are given below. Here, n- means normal, i- means iso, s- means secondary, and tert- means tertiary.

[0021] C １ ~C ６ Alkyl refers to a linear or branched hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl.

[0022] C １ ~C ６Alkoxy represents an alkyl - O - group having 1 to 6 carbon atoms as defined above, and examples thereof include methoxy, ethoxy, n - propyloxy, i - propyloxy, n - butyloxy, i - butyloxy, s - butyloxy, tert - butyloxy, n - pentyloxy, n - hexyloxy and the like.

[0023] Next, the production method of the compound (1) of the present invention will be described below. The compound (1) of the present invention can be produced by the following method. Hereinafter, the "compound represented by the formula (2)" is also referred to as "compound (2)". The same applies to other compounds. Also, room temperature is assumed to be within the range of 25 ° C ± 10 ° C, and normal pressure is assumed to be within the range of 0.1 to 0.13 MPa.

[0024] [Production method of the compound (1) of the present invention] The compound (1) of the present invention can be produced by reacting the compound (2) with hydroxylamine or alkoxyamine. That is, the compound (1) of the present invention is produced by oximating the compound (2). [In the formula, M represents a hydrogen atom or C １ ~C ６ alkyl, preferably a hydrogen atom or methyl. ]

[0025] Hydroxylamine and alkoxyamine may be used in the form of an aqueous solution or a salt such as a hydrochloride. The amount (equivalent) of hydroxylamine and alkoxyamine used can preferably be 0.9 to 3 equivalents, more preferably 0.9 to 1.5 equivalents, relative to 1 equivalent of the compound (2).

[0026] Compound (1) of the present invention can be produced by reacting compound (2) in a solvent. The solvent used is not particularly limited as long as it does not inhibit the reaction, but examples include hydrocarbon solvents such as hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, benzene, xylene, and toluene; halogenated hydrocarbon solvents such as dichloromethane, carbon tetrachloride, chloroform, 1,2-dichloroethane, chlorobenzene, and trifluoromethylbenzene; alcohol solvents such as methanol, ethanol, and 2-propanol; nitrile solvents such as acetonitrile and propionitrile; carboxylic acid ester solvents such as ethyl acetate and ethyl propionate; nitrogen-containing aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone; and water. Preferably, hydrocarbon solvents such as xylene and toluene, alcohol solvents such as methanol and ethanol, and water can be used. Two or more of these solvents can also be mixed. Among these, it is more preferable to use a solvent containing at least one of toluene and methanol. In particular, by using a mixed solvent of toluene and water, a mixed solvent of methanol and water, or a mixed solvent of toluene and methanol, the compound (1) of the present invention can be produced in high yield in a short time. However, when using a mixed solvent of methanol and water, if a large amount of water is present, the hydrolysis reaction of the compound (1) of the present invention will proceed more easily, so it is preferable that the water content in the mixed solvent be 50% by mass or less.

[0027] The reaction can also be carried out using a base. Examples of bases that can be used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate, calcium carbonate and potassium carbonate, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, and organic bases such as triethylamine, tributylamine, pyridine, 4-(dimethylamino)pyridine, imidazole, and 1,8-diazabicyclo[5,4,0]-7-undecene. Among these, alkali metal hydroxides are preferred, and sodium hydroxide is more preferred. In particular, when toluene is used as a solvent, compound (1) of the present invention can be quantitatively produced by using sodium hydroxide in combination. The amount of base used (equivalents) is preferably 1 to 10 equivalents, more preferably 1 to 4 equivalents, per equivalent of compound (2).

[0028] The reaction temperature is preferably 0 to 100°C, and more preferably 10 to 30°C. The reaction time varies depending on the type of reaction substrate and solvent, and the reaction temperature, but is preferably 10 minutes to 24 hours, and more preferably 10 minutes to 3 hours.

[0029] Compound (2) can be prepared by known methods described in the literature, for example, by methods described in Eur. J. Org. Chem. 2021, 1466-1473, etc.

[0030] The reaction mixture after the reaction is complete can be concentrated directly, or dissolved in an organic solvent and washed with water before concentration, or immersed in ice water, extracted with an organic solvent, and then concentrated. The desired reaction product can be obtained by these standard post-treatment methods. Furthermore, if purification is required, the mixture can be separated and purified using any purification method, such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatography preparative separation.

[0031] Next, a method for producing compound (3) will be described. Compound (3) may be in the form of the various salts described above, and may include all tautomers or mixtures of tautomers in any proportion, or all rotational isomers or mixtures of diastereomers in any proportion.

[0032] [Method for producing compound (3)] <Production example 1> Compound (3) can be produced by reducing compound (1) of the present invention in a hydrogen atmosphere. That is, hydrogen gas acts as a reducing agent, and compound (3) is produced by a reduction reaction (catalytic hydrogenation) in which hydrogen atoms are added to compound (1) of the present invention. Therefore, compound (3) corresponds to the reduction product of compound (1) of the present invention. [In the formula, M is a hydrogen atom or C １ ~C ６ This represents an alkyl group, preferably a hydrogen atom or a methyl atom.

[0033] Compound (3) can be produced by reacting compound (1) of the present invention in a solvent. There are no particular restrictions on the solvent used as long as it does not inhibit the progress of the reaction, but examples include hydrocarbon solvents such as hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; halogenated hydrocarbon solvents such as dichloromethane, carbon tetrachloride, chloroform, 1,2-dichloroethane, chlorobenzene, and trifluoromethylbenzene; alcohol solvents such as methanol, ethanol, and 2-propanol; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitrile solvents such as acetonitrile and propionitrile; carboxylic acid ester solvents such as ethyl acetate and ethyl propionate; nitrogen-containing aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone; and water. Preferably, aromatic hydrocarbon solvents such as xylene and toluene, alcohol solvents such as methanol and ethanol, and water can be used. Two or more of these solvents can also be used in mixture form. Among these, alcohol solvents are preferred, and methanol is particularly preferred.

[0034] The preparation of compound (3) may be carried out by adding an acid. Examples of acids that can be used include fatty acids such as formic acid, acetic acid, and trifluoroacetic acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and 4-methylbenzenesulfonic acid; carboxylic acids such as benzoic acid; phosphonic acids such as aminomethylphosphonic acid and phenylphosphonic acid; and inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid. It is preferable to select from the group consisting of acetic acid, hydrochloric acid, and sulfuric acid. Two or more of these acids can also be used in mixture form. Among these, hydrochloric acid and sulfuric acid are preferred. In particular, by using sulfuric acid, compound (3) can be prepared in high yield in a short time while reducing the amount of catalyst used. The acid is preferably used in an amount of 10 equivalents or less, more preferably 3 equivalents or less, and even more preferably 0.5 to 1.5 equivalents per equivalent of compound (1) of the present invention.

[0035] The reaction can be carried out in the presence of a catalyst. Examples of catalysts that can be used include palladium, platinum, and Raney nickel, with palladium and Raney nickel being preferred. These catalysts can be used in mixtures of two types, or they may be supported catalysts supported on carbon as a support. In the case of such carbon-supported catalysts, it is preferable that they be of the STD (standard) type. On the other hand, rhodium is not suitable as a catalyst for this reaction because it cannot accelerate the progress of the reaction. The amount of catalyst used can be 0.0001 to 0.8 equivalents per equivalent of compound (1) of the present invention, and the amount of catalyst added is preferably less than 10% by mass, more preferably 3% by mass or less, and even more preferably 2% by mass or less, relative to the amount of compound (1) added.

[0036] The hydrogen atmosphere can be maintained under normal pressure, but it may also be under higher pressure. When introducing hydrogen gas under pressure, the pressure is preferably 0.1 MPa-G or higher, and more preferably in the range of 0.1 MPa-G to 1 MPa-G. For example, when sulfuric acid is used as the acid and the hydrogen atmosphere is under a pressurized state of 0.3 MPa-G or higher, compound (3) can be quantitatively produced while reducing the amount of catalyst used.

[0037] The reaction temperature is preferably 0 to 50°C, and more preferably 10 to 30°C or room temperature. The reaction time varies depending on the type of reaction substrate and solvent, and the reaction temperature, but is preferably 1 to 48 hours, and more preferably 1 to 24 hours.

[0038] The reaction mixture after the reaction is complete can be concentrated directly, or dissolved in an organic solvent and washed with water before concentration, or immersed in ice water, extracted with an organic solvent, and then concentrated. The desired reaction product can be obtained by these standard post-treatment methods. Furthermore, if purification is required, the mixture can be separated and purified using any purification method, such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatography preparative separation.

[0039] <Production Example 2> Compound (3) can be produced by reacting compound (2) with ammonia and then reducing the resulting reaction product in a hydrogen atmosphere. Specifically, the -CHO group of compound (2) reacts with ammonia to form an imine, and then hydrogen gas acts as a reducing agent, adding hydrogen atoms to the formed imine in a reduction reaction (catalytic hydrogenation) to produce compound (3). Therefore, compound (3) can be produced directly from compound (2) without going through the production process of compound (1) of the present invention.

[0040] The imination of compound (2) can be carried out by reacting compound (2) with ammonia in a solvent. The solvent used is not particularly limited as long as it does not inhibit the reaction, but examples include hydrocarbon solvents such as hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, benzene, xylene, and toluene; halogenated hydrocarbon solvents such as dichloromethane, carbon tetrachloride, chloroform, 1,2-dichloroethane, chlorobenzene, and trifluoromethylbenzene; alcohol solvents such as methanol, ethanol, and 2-propanol; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitrile solvents such as acetonitrile and propionitrile; carboxylic acid ester solvents such as ethyl acetate and ethyl propionate; nitrogen-containing aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone; and water. Preferably, hydrocarbon solvents such as xylene and toluene, alcohol solvents such as methanol and ethanol, and water can be used. Two or more of these solvents can also be used in mixture form. Among these, alcohol solvents are preferred, methanol, ethanol, and 2-propanol are more preferred, and methanol is particularly preferred.

[0041] Ammonia may be used in the form of an aqueous solution (ammonia water), or an ammonia salt such as ammonium acetate may be used. The amount of ammonia used (in equivalents) can be 1 to 50 equivalents, more preferably 1 to 5 equivalents, per equivalent of compound (2). In other words, a small amount of ammonia can be used, specifically 50 equivalents or less, preferably 5 equivalents or less.

[0042] The imination of compound (2) can be carried out in the presence of a catalyst containing at least one of Raney nickel, Raney cobalt, palladium, and platinum. Among these, Raney nickel, palladium, and platinum are preferred. In particular, Raney nickel is preferred, as this suppresses the formation of the dimer of compound (3), which is a by-reactant. Two or more of these catalysts can be used in mixture form, and palladium and platinum may be supported catalysts supported on carbon as a support. The amount of catalyst used is preferably 0.0001 to 3 equivalents, more preferably 0.1 to 3 equivalents, per equivalent of compound (2).

[0043] The hydrogen atmosphere may be at normal pressure or under further pressurization. When introducing hydrogen gas under pressurization, the pressure is preferably 0.1 MPa-G or higher, and more preferably in the range of 0.1 to 1 MPa-G.

[0044] The reaction temperature is preferably 0 to 50°C, and more preferably 10 to 30°C or room temperature. The reaction time varies depending on the type of reaction substrate and solvent, and the reaction temperature, but specifically it can range from 1 to 48 hours. More preferably 1 to 24 hours, more preferably 1 to 7 hours, and even more preferably 1 to 4 hours.

[0045] The reaction mixture after the reaction is complete can be concentrated directly, or dissolved in an organic solvent and washed with water before concentration, or immersed in ice water, extracted with an organic solvent, and then concentrated. The desired reaction product can be obtained by these standard post-treatment methods. Furthermore, if purification is required, the mixture can be separated and purified using any purification method, such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatography preparative separation.

[0046] Compound (1) of the present invention exhibits herbicidal effects against various weeds and can be used as an active ingredient in herbicides. The application situation is not particularly limited, and when applied to paddy fields, it can be applied in either soil treatment or foliar treatment under flooded conditions.

[0047] Examples of rice paddy weeds include Chinese sprangletop (Leptochloa chinensis), bearded sprangletop (Leptochloa fascicularis), barnyard grass (Echinochloa crus-galli), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola), southern cutgrass (Leersia hexandra), knotgrass (Paspalum distichum), saramollagrass (Ischaemum rugosum), itchgrass (Rottboellia cochinchinensis), broadleaf signalgrass (Brachiaria platyphylla), and Alexandergrass. Grasses (Gramineae) such as Brachiaria plantaginea, large crabgrass (Digitaria sanguinalis), crowfootgrass (Dactyloctenium aegyptium), goosegrass (Eleusine indica), red rice (Oryza sativa), bermuda grass (Cynodon dactylon), and fall panicum (Panicum dichotomiflorum);Black water chestnut (Eleocharis kuroguwai), globe fringerush (Fimbristylis miliacea), Japanese bulrush (Schoenoplectus juncoides), Japanese bulrush (Schoenoplectus nipponicus), ricefield bulrush (Schoenoplectus mucronatus), water sedge (Cyperus serotinus), smallflower umbrella sedge (Cyperus difformis), rice flat sedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus), and cosmopolitan bulrush (Bolboschoenus) Cyperaceae weeds, such as martimus; Alismataceae weeds, such as water plantain (Alisma canaliculatum), pygmy arrowhead (Sagittaria pygmaea), and threeleaf arrowhead (Sagittaria trifolia); Commelinaceae weeds, such as Asian spiderwort (Murdannia keisak) and benghal dayflower (Commelina benghalensis);Weeds of the Pontederiaceae family, represented by Monochoria korsakowii (heartleaf false pickerelweed), Monochoria vaginalis (oval-leafed pondweed), Heteranthera limosa (ducksalad), and Eichhornia crassipes (water hyacinth); weeds of the Elatinaceae family, represented by Elatine triandra (threestamen waterwort); weeds of the Lythraceae family, represented by Ammannia coccinea (redstem) and Rotala indica (indian toothcup); weeds of Ludwigia epilobioides and Mexican primrose-willow, Weeds of the Onagraceae family, such as Ludwigia octovalvis; weeds of the Scrophulariaceae family, such as rushlike dopatrium (Dopatrium junceum), large dopatrium (Gratiola japonica), dwarf ambulia (Limnophila sessiliflora), prostrate false pimpernel (Lindernia pyxidaria), and yellowseed false pimpernel (Lindernia dubia); weeds of the Amaranthaceae family, such as alligator weed (Alternanthera philoxeroides) and spiny amaranth (Amaranthus spinosus); water pepper (Polygonum cuspidatum) Polygonaceae weeds, such as hydropiper;Weeds of the Sphenocleaceae family, such as gooseweed (Sphenoclea zeylanica); weeds of the Fabaceae family, such as Indian jointvetch (Aeschynomene indica) and hemp sesbania (Sesbania exaltata); weeds of the Asteraceae family, such as devil's beggarticks (Bidens frondosa), three-lobe beggarticks (Bidens tripartita), false daisy (Eclipta prostrata), and goatweed (Ageratum conyzoides); and swamp morningglory (Ipomoea Examples include weeds of the Convolvulaceae family, such as *Aquatica*; weeds of the Marsileaceae family, such as *Marsilea quadrifolia* (water clover); weeds of the Lemnaceae family, such as *Spirodela polyrhiza* (common duckmeat) and *Lemna paucicostata* (duckweed); and weeds of the Potamogetonaceae family, such as *Potamogeton distinctus* (roundleaf pondweed).

[0048] Compound (1) of the present invention can be applied in paddy fields as a simultaneous treatment during rice planting, in addition to the usual pre- and post-planting treatments. Furthermore, compound (1) of the present invention can be applied as a herbicide for fields and orchards by any of the following treatment methods: soil treatment, soil mixing treatment, and foliar treatment.

[0049] Common weeds in fields and orchards include, for example, fall panicum (Panicum dichotomiflorum), shattercane (Sorgham bicolor), Johnson grass (Sorgham halepense), barnyard grass (Echinochloa crus-galli var. crus-galli), cockspur grass (Echinochloa crus-galli var. praticola), cultivated barnyard millet (Echinochloa utilis), southern crabgrass (Digitaria ciliaris), sourgrass (Digitaria insularis), jamaican crabgrass (Digitaria horizontalis), wild oat (Avena fatua), and blackgrass (Alopecurus). myosuroides), shortawn foxtail (Alopecurus aequalis), windgrass (Apera spica-venti), downy brome (Bromus tectorum), Italian ryegrass (Lolium multiflorum), rigid ryegrass (Lolium rigidum), littleseed canarygrass (Phalaris minor), annual bluegrass (Poa annua), goosegrass (Eleusine indica), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), signalgrass,Poaceae weeds such as Brachiaria decumbens and southern sandbur (Cenchrus echinatus); Cyperaceae weeds such as purple nutsedge (Cyperus rotundus); Solanaceae weeds such as black nightshade (Solanum nigrum) and white jimsonweed (Datura stramonium); Malvaceae weeds such as velvetleaf (Abutilon theophrasti) and prickly sida (Sida spinosa); tall morning-glory (Ipomoea purpurea), ivyleaf morning-glory (Ipomoea Weeds of the Convolvulaceae family, such as Hederacea and Japanese bindweed (Calystegia hederacea); Weeds of the Amaranthaceae family, such as Purple amaranth (Amaranthus lividus), Redroot pigweed (Amaranthus retroflexus), Palmer amaranth (Amaranthus palmeri), and Tall waterhemp (Amaranthus tuberculatus); Common cocklebur (Xanthium strumarium), Common ragweed (Ambrosia artemisiifolia), Giant ragweed (Ambrosia trifida), Horseweed (Conyza canadensis), Sunflower (common) sunflower,Asteraceae weeds such as Helianthus annuus, pineappleweed (Matricaria matricarioides), hairy galinsoga (Galinsoga ciliata), Canadian thistle (Cirsium arvense), common groundsel (Senicio vulgaris), and annual fleabane (Erigeron annuus); Brassicaceae weeds such as variableleaf yellowcress (Rorippa indica), wild mustard (Sinapis arvensis), and shepherd's purse (Capsella bursa-pastoris); oriental lady's thumb (Persicaria longiseta), and wild buckwheat vine (wild Weeds of the Polygonaceae family, such as buckwheat (Polygonum convolvulus); weeds of the Portulacaceae family, such as common purslane (Portulaca oleracea); weeds of the Chenopodiaceae family, such as lamb's quarters (Chenopodium album), figleaved goosefoot (Chenopodium ficifolium), kochia (Kochia scoparia), and Russian thistle (Salsola tragus); weeds of the Caryophyllaceae family, such as common chickweed (Stellaria media); weeds of the Plantaginaceae family, such as persian speedwell (Veronica persica); Asiatic dayflower,Commelinaceae weeds, such as Commelina communis and Commelina benghalensis (benghal dayflower); Lamiaceae weeds, such as Lamium amplexicaule (henbit) and Lamium purpureum (purple deadnettle); Euphorbiaceae weeds, such as Euphorbia heterophylla (wild poinsettia) and Euphorbia maculata (spotted spurge); Rubiaceae weeds, such as Galium spurium (false cleavers) and Rubia akane (asian madder); and Viola tricolor (pansy). Examples include weeds of the Violaceae family, such as *Violaceae*; weeds of the Papaveraceae family, such as *Papaver rhoeas*; weeds of the Fabaceae family, such as *Sesbania exaltata* and *Cassia obtusifolia*; and weeds of the Oxalidaceae family, such as *Oxalis corniculata*.

[0050] Furthermore, compound (1) of the present invention can be applied in non-agricultural areas such as turflands, sports fields, open spaces, roadsides, and railway tracks, in addition to agricultural and horticultural fields such as paddy fields, cultivated fields, and orchards, using any of the following treatment methods: soil treatment, soil mixing treatment, and foliar treatment. In addition to those mentioned for weeds in fields and orchards, these weeds include annual bluegrass (Poa annua), dandelion (Taraxacum officinale), hairy fleabane (Conyza bonariensis), horseweed (Conyza canadensis), guernsey fleabane (Conyza sumatrensis), wavy bittercress (Cardamine flexuosa), white clover (Trifolium repens), lawn pennywort (Hydrocotyle sibthorpioides), Chinese plantain (Plantago asiatica), green kyllinga (Kylinga brevifolia), and field horsetail. Examples include Equisetum arvense.

[0051] Furthermore, compound (1) of the present invention can generally be used as a fungicide and mycicide for agricultural and horticultural purposes against various diseases caused by root-leaved molds, oomycetes, zygomycetes, ascomycetes, basidiomycetes, imperfect fungi, bacteria, or viruses.

[0052] "Pathogenic fungi" refers to microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms. Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. (e.g. Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g. Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii, etc.), Mycosphaerella spp. (e.g., Mycosphaerella arachidis, M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. (e.g., Paracercospora egenula, etc.), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g., Pseudocercospora abelmoschi, P. fuligena, P. vitis, etc.), Pseudocercosporella spp.(e.g., Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C.verruculosa spp., Drechslera spp., Pleospora spp., Pleospora herbarum spp., Pyrenophora spp. teres (Setosphaeria spp.) Setosphaeria turcica (Setosphaeria turcica) Stemphylium spp. lycopersici、S. solani、S. vesicarium spp., Venturia spp., Venturia carpophila, V. vesicarium spp. Inaequalis、V. nashicola、V. pyrin activity) and Didymella spp. fabae, Hendersonia spp., Phoma spp., Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae active) Pyrenochaeta spp spp. Botryosphaeria berengeriana f. sp. piricola、B. dothidea activity) Dothiorella spp. Fusicoccum spp. Guignardia spp. Lasiodiplodia spp spp. Phyllosticta spp.(also) Phyllosticta zingiberis spp.(also) Schizothyrium pomi spp.Acrospermum spp.Leptosphaerulina spp.Aspergillus spp., Penicillium spp.(from Penicillium digitatum, p. italicum、P. sclerotigenum spp., Trichophyton spp., Trichophyton mentagrophytes. rubrum spp., Histoplasma spp., Blumeria spp., Blumeria graminis f. sp. hordei、B. gf sp. tritici), Erysiphe spp. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. low activity) Golovinomyces spp. latisporus spp., Leveillula spp., Leveillula taurica spp., Microsphaera spp., Oidium spp., Oidium neolycopersici spp., Phyllactinia spp.(Phyllactinia kakicola)P. mali、P. moricola, Podosphaera spp., Podosphaera fusca, P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii activity) and Sphaerotheca spp. aphanis、S. fuliginea agent) and Uncinula spp. n. var. necator agent) (Uncinuliella spp.) Uncinuliella simulans var. simulans、U.S. s. var. tandae spp., Blumeriella jaapii spp., Cylindrosporium spp., Diplocarpon spp. mespili、D.rosae spp., Gloeosporium spp., Gloeosporium minus spp., Marssonina spp., Tapesia spp. yallundae, Lachnum spp., Scleromitrula spp., Botryotinia spp. byssoidea、B. cinerea、B. elliptic、B. fabae、B. squamosa agent) Ciborinia spp. Grovesinia spp. Monilia mumecola Monilinia spp. fructigena、M. laxa、M. mali、M. vaccinii-corymbosiactivity), Sclerotinia spp. homoeocarp、S. minor、S. sclerotiorum spp., Valdensia heterodoxa spp., Claviceps spp. sorghicola agent) Epichloe spp. Ephelis japonica Villosiclava virens Hypomyces spp. sp. mori、H. sf sp. low activity) Trichoderma spp.(also) Trichoderma viride activity) Calonectria spp.(an activity) Candelospora spp spp., Cylindrocladium spp., Fusarium spp. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. of sp.adzukicola, F. of sp. allii, F. of sp. asparagi, F. of sp. batatas, F. o. f. sp. cepae, F. of sp. colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp. lagenariae, F. of sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. of sp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sf sp. cucurbitae, F. sf sp. eumartii, F. sf sp. glycines, F. sf sp. pisi, F. sf sp. Radicicola, F. virguliforme, etc.), Gibberella spp. (e.g., Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g., Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp.(including Thielaviopsis basicola) and Adisciso spp. Monochaetia spp. (including Pestalotia eriobotrifolia spp.) in Pestalotiopsis spp.(Pestalotiopsis funerea) P. longiseta、P. neglecta、P. theae, Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp nivalis spp., Ophiostoma spp., Cryphonectria spp., Cryphonectria parasitica spp., Diaporthe spp. kyushuensis、D. nomurai、D. tanakae, Diaporthopsis spp., Phomopsis spp. fukushii、P. obscurans、P. vexans , Cryptosporella spp , Discula spp , Discula theae-sinensis , Gnomonia spp , Coniella spp , Coryneum spp , Greeneria spp , Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp.(also, Valsa ceratosperma activity) Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp.(such as Gaeumannomyces graminis) Magnaporthe spp.(such as Magnaporthe grisea) Pyricularia spp.(such as Pyricularia zingiberis (Monilochaetes infuscans), Colletotrichum spp.(e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C. lindemuthianum, C. nigrum, C. orbiculare, C. spinaciae, etc.), Glomerella spp. (e.g., Glomerella cingulata, etc.), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora Ascomycota fungi such as spp. (e.g., Philophora gregata), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., and Helicoceras oryzae. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g., Helicobasidium longisporum, etc.), Coleosporium spp. (e.g., Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. (e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.), Physopella spp. (e.g., Physopella ampelopsidis, etc.), Kuehneola spp.(including Kuehneola japonica species), Phragmidium spp.(including Phragmidium fusiforme), P. mucronatum、P. rosae-multiflorae agent) Gymnosporangium spp. yamadae) and Puccinia spp. brachypodii var. poae-nemoralis、P. crown、P. c. var. crown、P. cynodontis、P. graminis、P. g. subsp. graminicola、P. hordei、P. horiana、P. kuehnii、P. melanocephala、P. recondite、P. striiformis var. striiformis、P. tanaceti var. tanaceti、P. tokyensis、P. zoysiae, Uromyces spp., Uromyces phaseoli var. azukicola、U. p. var. phaseoli、Uromyces viciae-fabae var. viciae-fabae, Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp spp.(including Blastospora smilacis) Uredo spp. Sphacelotheca spp. Urocystis spp. Sporisorium spp spp.(Ustilago maydis,U. nuda, Entyloma spp., Exobasidium spp. vexans agent), Microstroma spp., Tilletia spp.(e.g., controversa, T. laevis), Itersonilia spp. (e.g., Itersonilia perplexans), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum), Conocybe spp. (e.g., Conocybe apala), Marasmius spp. (e.g., Marasmius oreades), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda), Sclerotium spp. (e.g., Sclerotium cepivorum), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis), Athelia spp. (e.g., Athelia Fungi of the phylum Basidiomycota, such as rolfsii, Ceratobasidium spp. (e.g., Ceratobasidium cornigerum), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani), Thanatephorus spp. (e.g., Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp. Fungi of the phylum Chitridiomycota, such as Olpidium spp. Fungi of the phylum Blastocladiomycota, such as Physoderma spp. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R.Fungi of the subphylum Mucoromycotina such as stolonifer var. stolonifer, etc. Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g., Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (e.g., Peronospora alliariae - wasabi, P. chrysanthemi - coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g., Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (e.g., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (e.g., Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P.debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P. ultimum var. ultimum, P. vanterpoolii, P. Oomycetes of the phylum Heterokontophyta, such as P. vexans, P. volutum, etc. Gram-positive bacteria of the phylum Actinobacteria, such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli), and Streptomyces spp. (e.g., Streptomyces ipomoeae). Gram-positive bacteria of the phylum Firmicutes, such as Clostridium sp. Gram-positive bacteria of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g., Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g., Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g., Acidovorax avenae subsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. (e.g., Xanthomonas albilineans, X. arboricola pv. pruni, X. axonopodis pv. vitians, X.campestris e.g. campestris、X. c. e.g. cucurbitae、X. c. e.g. glycines、X. c. e.g. mangiferaeindicae、X. c. e.g. nigromaculans、X. c. e.g. vesicatory、X. citri subsp. citri、X. oryzae e.g. oryzae) and Pseudomonas spp. fluorescence、P. marginalis、P. m. e.g. marginalis、P. savastanoi e.g. glycinea、P. syringae、P. s. e.g. actinidiae、P. s. e.g. eriobotryae、P. s. e.g. helianthi、P. s. e.g. lachrymans、P. s. e.g. maculicola、P. s. e.g. mori、P. s. e.g. morsprunorum, P. s. e.g. spinaciae、P. s. e.g. syringae、P. s. e.g. theae、P. viridiflava spp., Rhizobacter spp., Brenneria spp., Brenneria nigrifluens spp., Dickeya spp. zeae, Erwinia spp., Erwinia amylovora, E. rhapontici, Pantoea spp., Pectobacterium spp. carotovorum, P. carotovorum. wasabiae (Proteobacteria).

[0053] Specific examples of plant diseases caused by infection and proliferation of these pathogens include, but are not limited to, the following. Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), sugar beet leaf spot (Cercospora beticola), bell pepper frogeye leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown leaf spot (Mycosphaerella arachidis), cherry brown leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), black sigatoka (Mycosphaerella fijiensis), yellow sigatoka (Mycosphaerella ell Musicola, Wheat leaf blotch (Mycosphaerella graminicola), Persimmon leaf spot (Mycosphaerella nawae), Pea brown spot (Mycosphaerella pinodes), Ginger leaf spot (Mycosphaerella zingiberis), Tomato leaf mold (Mycovellosiella fulva), Eggplant leaf mold (Mycovellosiella nattrassii), Tomato leaf mold (Pseudocercospora fuligena), Grape leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spotLeaf spot (Pseudocercosporella capsellae), Chrysanthemum black spot (Leaf spot (Septoria chrysanthemella)), Chrysanthemum brown spot (Leaf blight (Septoria obesa)), Grape black rot (Anthracnose (Elsinoe ampelina)), Aralia scab (Spot anthracnose (Elsinoe araliae)), Citrus scab (Scab (Elsinoe fawcettii)), Pea brown spot (Leaf spot (Ascochyta pisi)), Cucumber brown spot (Corynespora leaf spot (Corynespora cassiicola)), Rose branch blight (Stem canker (Leptosphaeria coniothyrium)), Wheat flammability (Glume blotch (Leptosphaeria nodorum)), Rose black spot (Leaf spot (Alternaria alternata)), Cabbage black spot (Alternaria leaf spot (Alternaria brassicae)), Carrot black leaf blight (Leaf blight (Alternaria dauci), pear black spot (Alternaria kikuchiana), apple leaf spot (Alternaria mali), onion leaf spot (Alternaria porri), sorghum purple spot (Bipolaris sorghicola), corn southern leaf blight (Cochliobolus heterostrophus), rice brown spot (Cochliobolus miyabeanus), garlic tip blight (Pleospora herbarum), barley stripe (Pyrenophora graminea), barley net blotch (Pyrenophora teres), sorghum leaf blight (Setosphaeria turcica), corn northern leaf blight (Setosphaeria turcica)turcica), asparagus leaf spot (Stemphylium botryosum), black spot (Venturia carpophila), apple scab (Venturia Inaequalis), pear scab (Venturia nashicola), gummy stem blight (Didymella bryoniae), burdock leaf spot (Phoma exigua var. exigua), wasabi streak (Phoma wasabiae), ring rot (Botryosphaeria berengeriana f. sp. piricola), kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), common green mold (Penicillium digitatum), citrus blue mold Powdery mildew (Penicillium italicum), which occurs in various crops, including barley powdery mildew (Blumeria graminis f. sp. hordei), wheat powdery mildew (Blumeria graminis f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), and bell pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (OidiumPowdery mildew of oysters (Phyllactinia kakicola), powdery mildew of burdock (Podosphaera fusca), powdery mildew of apples (Podosphaera leucotricha), powdery mildew of roses (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), powdery mildew of zucchini and cantaloupe (Podosphaera xanthii), powdery mildew of strawberries (Sphaerotheca aphanis var. aphanis), powdery mildew of watermelons and melons (Sphaerotheca fuliginea), powdery mildew of grapes (Uncinula necator, U. n. var. necator), apple blotch (Diplocarpon mali), rose black spot (Diplocarpon rosae), gray mold neck rot of onions (Botrytis Allii), Gray mold, Botrytis blight (Botrytis cinerea), Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Blossom blight (Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut (Villosiclava virens), Root necrosis (Calonectria sclerotiorum) Fusarium blight (Fusarium crookwellense, F. culmorum,Gibberella avenacea, G. zeae, Monographella nivalis), Fusarium blight of barley (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of taro (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), Fusarium wilt of adzuki bean (Fusarium oxysporum f. sp. adzukicola), Fusarium basal rot of Japanese arrowroot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem rot of sweet potato (Fusarium oxysporum f. sp. batatas, F. solani), Dry rot of taro (Fusarium oxysporum f. sp. colocasiae), Yellows of cabbage and Komatsuna (Fusarium oxysporum f. sp. conglutinans), Panama disease of banana (Fusarium oxysporum f. sp. cubense), Fusarium wilt of strawberry (Fusarium oxysporum f. sp. fragariae), Root rot of lettuce (Fusarium oxysporum f. sp. lactucae), Fusarium wilt of watermelon (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), Fusarium wilt of tomato (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt of melon (Fusarium oxysporum f. sp. melonis), Yellows of radish (Fusarium oxysporum f.Fusarium sp. raphani), spinach wilt (Fusarium oxysporum f. sp. spinaciae), soybean sudden death syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), rice bakanae disease (Gibberella fujikuroi), radish verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, eggplant, and butterbur verticillium wilt (Verticillium dahliae), fig canker (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), tea ring spot (Pestalotiopsis longiseta, P. theae), Endothia canker (Cryphonectria parasitica), Citrus black spot (Diaporthe citri), Asparagus stem blight (Phomopsis asparagi), Pear canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Apple canker (Valsa ceratosperma), Rice blast (Magnaporthe grisea), Strawberry anthracnose (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), Apple anthracnose (Bitter rot (Colletotrichum acutatum, Glomerella cingulata), Anthracnose (Colletotrichum acutatum, Glomerella)Anthracnose of plums (Colletotrichum acutatum), Ripe rot of grapes (Colletotrichum acutatum, Glomerella cingulata), Anthracnose of chrysanthemums (Colletotrichum acutatum), Anthracnose of kidney beans (Colletotrichum lindemuthianum), Anthracnose of cucurbits (Colletotrichum orbiculare), Anthracnose of yams (Glomerella cingulata), Anthracnose of chestnuts (Glomerella cingulata), Anthracnose of persimmons (Glomerella cingulata), Brown stem rot of adzuki beans (Phialophora gregata), Leaf spot of yams (Pseudophloeosporella sporata Dioscoreae), barley scald (Rhynchosporium secalis), wheat brown rust (Puccinia recondita), wheat stripe rust (Puccinia striiformis), rust affecting various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), pear cedar-apple rust (Gymnosporangium asiaticum), apple cedar-apple rust (Gymnosporangium yamadae), rust affecting onions (Puccinia allii), chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisorium)scitamineum), corn smut (Ustilago maydis), barley loose smut (Ustilago nuda), tea net blister blight (Exobasidium reticulatum), tea blister blight (Exobasidium vexans), white mold, stem rot, southern blight (Athelia rolfsii), chrysanthemum root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage seedling damping-off (Rhizoctonia solani), Japanese parsley damping-off (Rhizoctonia solani), lettuce bottom rot (Rhizoctonia solani), grass leaf blight (Brown patch, Large patch, Rhizoctonia solani), rice sheath blight blight (Thanatephorus cucumeris), sugar beet root rot (Thanatephorus cucumeris), sugar beet leaf blight (Thanatephorus cucumeris), fig black mold (Rhizopus rot, Rhizopus stolonifer var. stolonifer), clubroot (Plasmodiophora brassicae), sugar beet black root rot (Aphanomyces cochlioides), white rust (Albugo macrospora), downy mildew affecting various crops, lettuce downy mildew (Bremia lactucae), garland chrysanthemum downy mildew (Peronospora chrysanthemi-coronarii), onion and leek downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp.) spinaciae, soybean mildew (PeronosporaDowny mildew of manshurica, Brassicaceae (Peronospora parasitica), rose downy mildew (Peronospora sparsa), sunflower downy mildew (Plasmopara halstedii), three-leaf downy mildew (Plasmopara nivea), grape downy mildew (Plasmopara viticola), Cucurbitaceae downy mildew (Pseudoperonospora cubensis), Aralia elata root rot (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), pumpkin rot (Phytophthora capsici), bell pepper rot (Phytophthora capsici), watermelon rot (Phytophthora cryptogea), tomato and potato late blight (Phytophthora infestans), fig rot (White powdery blight) rot (Phytophthora palmivora), white blight of the onion family (Phytophthora porri), soybean stem blight (Phytophthora root and stem rot) (Phytophthora sojae), adzuki bean stem blight (Phytophthora vignae f. sp. adzukicola), spinach damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), konjac root rot (Pythium aristosporum), corn root rot (Pythium arrhenomanes, P. graminicola), cabbage seedling damping-off (Pythium buismaniae, P. myriotylum), myoga rhizome rot (Pythium myriotylum), ginger rhizome rot (root disease)rot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato canker (Clavibacter michiganensis subsp. michiganensis), potato scab (Streptomyces spp.), rose crown gall (Rhizobium radiobacter), sorghum bacterial stripe (Burkholderia andropogonis), onion soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), rice bacterial grain rot (Burkholderia gladioli, B. glumae), watermelon bacterial fruit blotch (Acidovorax avenae subsp. Bacterial leaf blight (Acidovorax konjaci), Bacterial leaf blight (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria) nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial leaf spot (Xanthomonas axonopodis pv. vitians), Black rot (Xanthomonas campestris pv. campestris), Bacterial pustule (Xanthomonas campestris pv. glycines), burdock black spot bacterial disease Bacterialspot (Xanthomonas campestris pv. nigromaculans), bacterial spot on bell pepper (Xanthomonas campestris pv. vesicatoria), citrus canker (Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), bacterial blossom blight on kiwi fruit (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), bacterial canker on kiwi fruit (Pseudomonas syringae pv. Actinidiae), loquat canker (Pseudomonas syringae pv. eriobotryae), bacterial spot on cucurbits (Pseudomonas syringae pv. lachrymans), bacterial black spot on brassicas (Pseudomonas syringae pv. maculicola), bacterial canker on plums (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), bacterial shoot blight on tea leaves (Pseudomonas syringae pv. theae), bacterial soft rot on leeks (Dickeya sp., Pectobacterium carotovorum), fire blight on roses (Erwinia amylovora), soft rot on konjac (Pectobacterium carotovorum), bacterial soft rotrot (Pectobacterium carotovorum).

[0054] In addition to its use as a fungicide and mycotic for agricultural and horticultural purposes, compound (1) of the present invention can also be used as a medical antimicrobial agent and veterinary antimicrobial agent used as an antifungal agent or internal parasite control agent, as well as an antibacterial and antifungal agent for wood, paper and pulp, adhesives and paints, textiles and leather, etc., and as an industrial disinfectant for cooling water channels in manufacturing plants, etc.

[0055] Examples of pathogenic fungi targeted by antifungal agents include, but are not limited to, dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, and Cryptococcus fungi such as Cryptococcus neoformas.

[0056] Examples of internal parasites that may be targeted include, but are not limited to, the following: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Couperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, and Strongirus. Nematodes such as *Trichonema*, *Dictyocaulus*, *Capillaria*, *Heterakis*, *Toxocara*, *Ascaridia*, *Oxyuris*, *Ancylostoma*, *Uncinaria*, *Toxascaris*, and *Parascaris*; Nematodes of the family Filariidae, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Nematodes of the family Dracunculidae, such as Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, and Echinococcus granulosus Tapeworms such as *Echinococcus granulosus* and *Echinococcus multilocularis*; liver fluke (*Fasciola hepatica*, F.Species such as giantantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonochis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, and other trematodes; Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria obioidalis Eimeria spp. (such as *Eimeria ovinoidalis*); Trypanosomsa cruzi; Leishmania spp.; Plasmodium spp. (malaria parasite); Babesia spp.; Trichomonadidae spp.; Histomanas spp.; Giardia spp.; Toxoplasma spp.; Entamoeba histolytica; Theileria spp., etc.

[0057] In addition to those mentioned for antifungals and internal parasites, the pathogens targeted by medical or veterinary antibacterial agents include, but are not limited to, dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida such as Candida albicans, Aspergillus such as Aspergillus fumigatus, Cryptococcus such as Cryptococcus neoformas, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae, and Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0058] Examples of fungal strains targeted as antibacterial and antifungal agents include wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor, and material degradation microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria, but are not limited to these.

[0059] Examples of fungal strains targeted for industrial use include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera. In addition to their use as fungicides in agriculture and horticulture, the compounds of the present invention can also be used as agents to control internal parasites in livestock, poultry, or pet animals.

[0060] <Examples of Formulations> When using compound (1) of the present invention as a herbicide or fungicide, compound (1) of the present invention is usually mixed with a suitable solid or liquid carrier, and optionally a surfactant, penetrating agent, spreading agent, thickener, antifreeze, binder, anticaking agent, disintegrant, or decomposition inhibitor is added to produce a formulation in any dosage form, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granule, water-soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, or gel. Furthermore, from the viewpoint of saving labor and improving safety, the formulation in any of the above dosage forms can also be provided enclosed in a water-soluble package.

[0061] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, or diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, or potassium chloride; synthetic silicic acid; or synthetic silicates.

[0062] Examples of liquid carriers include alcohol solvents such as ethylene glycol, propylene glycol, or isopropanol; aromatic hydrocarbon solvents such as xylene, alkylbenzene, or alkylnaphthalene; ether solvents such as butyl cellosolve; ketone solvents such as cyclohexanone; ester solvents such as γ-butyrolactone; acid amide solvents such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, or castor oil; or water. These solid and liquid carriers may be used individually or in combination of two or more.

[0063] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, or polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, or polystyrene sulfonates; cationic surfactants such as alkylamine salts or alkyl quaternary ammonium salts; or amphoteric surfactants such as amino acid type or betaine type.

[0064] The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by mass per 100 parts by mass of the formulation. Furthermore, these surfactants may be used individually or in combination of two or more types.

[0065] When compound (1) of the present invention is used as an agricultural chemical, it may be mixed and applied with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, or soil conditioners, as needed, at the time of formulation or application. In particular, by mixing and applying it with other agricultural chemicals or plant hormones, it is possible to reduce costs by decreasing the amount of chemicals applied, expand the fungicidal and insecticidal spectrum through the synergistic effect of the mixed chemicals, or achieve a higher pest control effect. In this case, it is also possible to combine it with multiple known agricultural chemicals at the same time.

[0066] One example of the type of pesticide used in mixture with compound (1) of the present invention is a compound described in The Pesticide Manual, 18th edition, 2018.

[0067] The amount of compound (1) of the present invention to be applied varies depending on the application situation, timing of application, method of application, or cultivated crop, but generally, an amount of 0.005 to 50 kg per hectare (ha) as the amount of active ingredient is appropriate, and 0.01 to 1 kg is preferred.

[0068] Next, examples of formulations using compound (1) of the present invention are shown. However, the examples of formulations containing compound (1) of the present invention are not limited to these. In the following examples of formulations, "parts" means parts by mass.

[0069] [Wettable Powder] Compound (1) of the present invention: 0.1 to 80 parts solid carrier, 5 to 98.9 parts surfactant, 1 to 10 parts other, 0 to 5 parts other, for example, an anti-caking agent or a decomposition inhibitor.

[0070] [Emulsion] Compound of the present invention (1) 0.1 to 30 parts liquid carrier 45 to 95 parts surfactant 4.9 to 15 parts other 0 to 10 parts other, for example, spreading agents or decomposition inhibitors.

[0071] [Suspension agent] Compound (1) of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreeze or thickener.

[0072] [Granular wettable powder] Compound of the present invention (1) 0.1 to 90 parts solid carrier 0 to 98.9 parts surfactant 1 to 20 parts other 0 to 10 parts other, for example, a binder or a decomposition inhibitor.

[0073] [Liquid Formulation] Compound of the present invention (1) 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreeze or spreading agents.

[0074] [Granules] Compound of the present invention (1) 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders or decomposition inhibitors.

[0075] [Powder] Compound of the present invention (1) 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, drift inhibitors or decomposition inhibitors.

[0076] For use of the formulation, for example, the above-mentioned formulation may be diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or sprayed without dilution.

[0077] Next, we will show more specifically examples of formulations containing compound (1) of the present invention as an active ingredient, but these formulations are not limited to these, including compound (1) of the present invention. Note that No. 1-1 in compound (1) of the present invention shown below refers to (E)-1,1,1-trifluoro-N-(2-((hydroxyimino)methyl)phenyl)methanesulfonamide, as described in Example 1-2 described later. Also, in the following production examples, "parts" refers to parts by mass.

[0078] [Formulation Example 1] Emulsion Compound No. 1-1 of the present invention 5 parts Xylene 75 parts N-methyl-2-pyrrolidone 15 parts Sorpole 2680 5 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) The above components are uniformly mixed to form an emulsion. When using the emulsion, the emulsion is diluted with water 50 to 20,000 times and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0079] [Formulation Example 2] Wettable Powder Compound No. 1-1 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Carplex (registered trademark) #80D 3 parts (White carbon: manufactured by DSL Japan, trade name) Calcium ligninsulfonate 2 parts The above components are uniformly mixed and pulverized to make a wettable powder. When using the wettable powder, dilute the wettable powder with water 50 to 20,000 times and spray so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0080] [Formulation Example 3] Powder Formulation Compound No. 1-1 3 parts Carplex (registered trademark) #80D 0.5 parts (White carbon: manufactured by DSL. Japan, trade name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and ground to form a powder. When using the powder, the amount of the active ingredient in the powder should be 0.005 to 50 kg per hectare.

[0081] [Formulation Example 4] Granular Formulation of the present invention compound No. 1-1 5 parts bentonite 30 parts talc 64 parts calcium ligninsulfonate 1 part The above components are uniformly mixed and ground, a small amount of water is added and stirred, granulated using an extrusion granulator, and dried to obtain granules. When using the granules, the amount of active ingredient of the granules is to be spread so that it is 0.005 to 50 kg per hectare.

[0082] [Formulation Example 5] Flowable formulation Compound No. 1-1 of the present invention 25 parts Solpol 3353 5 parts (nonionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Lunox 1000C 0.5 parts (anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts The above components, excluding the active ingredient (compound No. 1-1 of the present invention), are uniformly dissolved, then compound No. 1-1 of the present invention is added and stirred well, and then wet-milled in a sand mill to obtain a flowable formulation. When using the flowable formulation, the flowable formulation is diluted with water 50 to 20,000 times and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0083] [Formulation Example 6] Dry Flowable Formulation Compound No. 1-1 75 parts Hightenol (registered trademark) NE-15 5 parts (anionic surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name) Vanirex (registered trademark) N 10 parts (anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd., trade name) Carplex (registered trademark) #80D 10 parts (white carbon: manufactured by DSL. Japan, trade name) The above components are uniformly mixed and finely ground, a small amount of water is added and stirred and mixed, granulated using an extrusion granulator, and dried to obtain a dry flowable formulation. When using the dry flowable formulation, dilute it with water 50 to 20,000 times and spray so that the active ingredient is 0.005 to 50 kg per hectare.

[0084] Methods of applying the compound (1) of the present invention include foliar application, soil treatment, and seed disinfection, but it is also effective using general methods commonly used by those skilled in the art.

[0085] Based on the above, embodiments of the present invention relate to the following [1] to

[14] . [1] Formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６[2] A trifluoromethanesulfonanilide compound or a salt thereof represented by [1], wherein M is a hydrogen atom or a methyl atom. [3] Formula (2): A compound represented by or a salt thereof is dissolved in a solvent with hydroxylamine or C １ ~C ６ When reacted with an alkoxyamine having an alkoxy group, formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by [representing alkyl]. [4] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to [3], wherein the solvent comprises at least one of water, toluene, and methanol. [5] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to [3] or [4], wherein the reaction is carried out in the presence of a base. [6] Formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A trifluoromethanesulfonanilide compound represented by [representing alkyl] or a salt thereof is reduced in a hydrogen atmosphere in the presence of a catalyst to obtain formula (3): A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by formula (1). [7] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to [6], wherein the catalyst comprises at least one of Raney nickel, palladium, and platinum. [8] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to [6] or [7], further comprising adding an acid to carry out the reduction. [9] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to any one of [6] to [8], wherein the acid is selected from the group consisting of acetic acid, hydrochloric acid, and sulfuric acid.

[10] The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to any one of [6] to [9], wherein the amount of catalyst used is 0.0001 to 0.8 equivalents per equivalent of the trifluoromethanesulfonanilide compound or a salt thereof represented by formula (1).

[11] A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to any one of [6] to

[10] , wherein the hydrogen atmosphere is further pressurized.

[12] Formula (2): The compound represented by is reacted with ammonia in the presence of a catalyst containing at least one of Raney nickel, palladium, and platinum, and the resulting reaction product is further reduced in a hydrogen atmosphere to obtain formula (3): A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by

[13] . A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to

[12] , wherein the compound is reduced in a hydrogen atmosphere under normal pressure.

[14] A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to

[12] or

[13] , wherein the compound represented by formula (2) is reacted with 5 equivalents or less of ammonia.

[0086] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0087] Furthermore, the following proton nuclear magnetic resonance chemical shift values ​​(hereinafter,１ The chemical shift values ​​(referred to as H-NMR) were measured in deuterated chloroform solvent at 300 MHz (model: ECX300, JEOL) or 400 MHz (model: JNM-ECZ400S, JEOL). The symbols in the proton nuclear magnetic resonance chemical shift values ​​represent the following: s: singlet, d: doublet, t: triplet, q: quartet, br: broad. The products obtained in the following synthesis examples are: １ Analysis was performed using H-NMR.

[0088] Furthermore, the analytical conditions for HPLC (High-Performance Liquid Chromatography) are as follows: Column: Inert Sustain C18, 250 mm, 4.6 mmφ, 5 μm (GL Sciences Co., Ltd.) Flow rate: 1.0 mL / min Column temperature: 40°C UV detection wavelength: 254 nm or 220 nm Eluent: Acetonitrile / 0.1 vol% trifluoroacetic acid aqueous solution = 45 / 55 (0-30 min) - 90 / 10 (32-38 min) - 45 / 55 (40-45 min) (volume ratio) Internal standard: 1,4-diethoxybenzene

[0089] <Synthesis Example> [Example 1-1] Preparation of (E)-1,1,1-trifluoro-N-(2-((methoxyimino)methyl)phenyl)methanesulfonamide (hereinafter referred to as compound (1-2)) A mixed solution of 0.50 g of 1,1,1-trifluoro-N-(2-formylphenyl)methanesulfonamide (hereinafter referred to as compound (2-1)) and 2.50 g of toluene is mixed with 0.57 g of 30% by mass NaOH aqueous solution and 25% by mass NH ２ OCH ３ 0.67 g of HCl aqueous solution was added. After the addition was complete, the reaction mixture was stirred under a nitrogen atmosphere at 25°C for 3 hours. Next, 5.02 g of compound (2-1), 25.0 g of toluene, 5.70 g of 30% by mass of NaOH aqueous solution and 25% by mass of NH4 were added to the reaction mixture. ２ OCH ３6.8 g of aqueous HCl solution was added. After the addition was complete, the reaction mixture was stirred at the same temperature for 1 hour. After the reaction was complete, the mixture was separated. The obtained organic layer was extracted with 14 g of 10% NaOH aqueous solution. After combining the obtained aqueous layers, 8.2 g of 35% hydrochloric acid was added, and the mixture was extracted with 16.5 g of toluene. The obtained organic layer was washed with 11.0 g of water, then dehydrated and dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 6.04 g of the target product as a yellow solid (yield 97.4%).

[0090] Melting point: 47-49°C １ H-NMR (400MHz): δ10.99 (s, 1H), 8.13 (s, 1H), 7.73-7.71 (m, 1H), 7.40-7.35 (m, 1H), 7.25-7.21 (m, 2H), 4.00 (s, 3H)

[0091] [Example 1-2] Production of (E)-1,1,1-trifluoro-N-(2-((hydroxyimino)methyl)phenyl)methanesulfonamide (hereinafter referred to as compound (1-1)) A mixed solution of compound (2-1) and toluene is mixed with 75.0 g of 10% by mass NaOH aqueous solution and NH ２ 4.54 g of OH·HCl was added. After the addition was complete, the mixture was stirred under a nitrogen atmosphere at 25°C for 2.5 hours. After the reaction was complete, the mixture was separated. The obtained organic layer was extracted with 40 g of 10% NaOH aqueous solution. After combining the obtained aqueous layers, 23.0 mL of 35% hydrochloric acid was added and the mixture was extracted with 45.0 g of toluene. Next, 5.0 mL of 35% hydrochloric acid was added to the aqueous layer and the mixture was extracted with toluene (45.0 g x 2 times). After combining the obtained organic layers, the mixture was dehydrated and dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15.3 g of the target product as a yellow solid (yield 96.2%).

[0092] Melting point: 71-74°C １ H-NMR (400MHz): δ10.82 (s, 1H), 8.21 (s, 1H), 7.73-7.71 (m, 1H), 7.47 (s, 1H), 7.41-7.37 (m, 1H), 7.29 (dd, 1H, J = 7.7, 3.9 Hz), 7.21 (dd, 1H, J = 7.7, 3.9 Hz)

[0093] [Example 1-3] Preparation of compound (1-1) To a mixed solution of compound (2-1) 80.0 g and toluene 370 g, 253 g of a 6% by mass NaOH aqueous solution was added and stirred at 60°C for 0.5 hours. After the reaction was complete, liquid-liquid separation was performed. In the aqueous layer containing the sodium salt of compound (2-1), 274 g of a 6% by mass NaOH aqueous solution and 25% by mass NH4 were added at 10°C. ２ 89.6 g of aqueous OH·HCl solution was added and the mixture was stirred at the same temperature for 1 hour. After the reaction was complete, 320 g of toluene and 98.7 g of 35% by mass hydrochloric acid were added and the mixture was separated. The resulting organic layer was washed twice with 160 g of water to obtain 467 g of a toluene solution containing 17.9% by mass of the target product (yield 99.0%). 168 g of the obtained toluene solution was taken, concentrated under reduced pressure, and then 21 g of toluene and 42 g of heptane were added and the mixture was stirred at 60°C. The solution was cooled to 52°C, 0.3 g of compound (1-1) was added, and solid precipitation was confirmed. The mixture was cooled to 30°C, 42 g of heptane was added, and the mixture was stirred at the same temperature for 0.5 hours. The mixture was further cooled to 0°C and stirred at the same temperature for 11 hours. The solid was filtered, washed with a mixed solution of 3.0 g of toluene and 27.0 g of heptane, and dried under reduced pressure to obtain 26.3 g of the target product as a yellow solid (yield 86.7%).

[0094] [Example 1-4] Preparation of compound (1-1) To a mixed solution of compound (2-1) 3.96 g and toluene 18.5 g, 2.37 g of sodium sulfite and 11.9 g of water were added and stirred at 30°C for 1 hour. After the reaction was complete, liquid-liquid separation was performed. In the aqueous layer, which is presumed to contain sodium hydroxy(2-(trifluoromethyl)sulfonamide)phenyl)methanesulfonate, 1.56 g of NaOH and 25% by mass of NH4 were added at 10°C. ２ 4.43 g of aqueous OH·HCl solution was added and the mixture was stirred at the same temperature for 1 hour. After the reaction was complete, 15.8 g of toluene and 4.89 g of 35% by mass hydrochloric acid were added and the mixture was separated. The resulting organic layer was washed twice with 7.9 g of water, dehydrated and dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3.77 g of the target product as a yellow solid (yield 89.9%).

[0095] [Example 2-1] To a mixed solution of 1.02 g of compound (1-2) and 10 g of methanol, a sulfate preparation compound of N-(2-(aminomethyl)phenyl)-1,1,1-trifluoromethanesulfonamide (hereinafter referred to as compound (3-1)) was prepared. To this solution, 0.38 g of 95% sulfuric acid and 0.009 g of 5% palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% water content) were added. After the addition was complete, the resulting reaction mixture was stirred at 25°C for 8 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 1.18 g of the target product (yield 93.1%).

[0096] [Examples 2-2 to 2-3] Production of sulfate of compound (3-1) To a mixed solution of 1.50 g of compound (1-1) and 15 g of methanol, 0.59 g of 95% by mass sulfuric acid and 0.015 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% by mass water content) were added. After the addition was complete, the resulting reaction mixture was stirred at 10°C for 27 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 1.87 g of the target product (yield 94.9%).

[0097] Furthermore, the reaction was carried out under the same conditions as described above, except for changes in reaction temperature and reaction time. The reaction temperature, reaction time, and yield are shown in Table 1 below.

[0098]

[0099] [Example 2-4] Production of sulfate of compound (3-1) To a mixed solution of 0.74 g of compound (1-1) and 7.4 g of methanol, 0.29 g of 95% by mass sulfuric acid and 0.0074 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% water content) were added. After the addition was complete, the resulting reaction mixture was stirred at 35°C for 4 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 0.90 g of the target product (yield 92.9%).

[0100] [Examples 2-5 to 2-6] Preparation of sulfate of compound (3-1) 1.50 g of compound (1-1), 15.0 g of methanol, 0.58 g of 95% by mass sulfuric acid, and 0.015 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% hydrated) were charged into a 200 mL autoclave. The mixture was stirred under a 0.3 MPa-G hydrogen atmosphere at 10°C for 13 hours under magnetic stirring. After the reaction was complete, the resulting reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 1.87 g of the target product (yield 96.1%).

[0101] Furthermore, the reaction was carried out under the same conditions as described above, except for changes in reaction temperature and reaction time. The reaction temperature, reaction time, and yield are shown in Table 2 below.

[0102]

[0103] [Example 2-7] Preparation of sulfate of compound (3-1) 5.02 g of compound (1-1), 50.0 g of methanol, 0.05 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% hydrated) and 1.84 g of 98% by mass sulfuric acid were charged into a 200 mL autoclave. The mixture was stirred at 10°C for 13.5 hours under a 0.3 MPa-G hydrogen atmosphere with a magnetic stirrer. After the reaction was complete, the resulting reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 6.26 g of the target product (yield 96.9%).

[0104] [Example 2-8] Production of sulfate of compound (3-1) To a mixed solution of 1.50 g of compound (1-1) and 15 g of methanol, 0.57 g of 95% by mass sulfuric acid, 0.58 g of trimethyl orthoformate (dehydrating agent), and 0.015 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% water content) were added. After the addition was complete, the resulting reaction mixture was stirred at 25°C for 7 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 1.87 g of the target product (yield 96.6%).

[0105] [Example 2-9] Preparation of compound (3-1) 0.32 g of Raney nickel (manufactured by Tokyo Chemical Industry Co., Ltd., Skeletal Nickel Catalyst slowly in Water [Active Catalyst for Hydrogenation]), 5.73 g of 6% by mass NaOH aqueous solution, and 2.00 g of compound (1-1) were added, and the resulting mixture was stirred at 25°C for 78 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the Raney nickel, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 1.57 g of the target product (yield 82.8%).

[0106] [Example 3-1] Preparation of compound (3-1) 0.4 g of Raney nickel (manufactured by Tokyo Chemical Industry Co., Ltd., Skeletal Nickel Catalyst slowly in Water [Active Catalyst for Hydrogenation]) was weighed and the supernatant was removed. The residue was washed with methanol (1 mL x 3 times), and then 10 g of methanol, 0.76 g of 28% by mass aqueous ammonia solution and 0.63 g of compound (2-1) were added. After the addition was complete, the resulting reaction mixture was stirred at 25°C for 4 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the Raney nickel, and the filtrate was washed with acetonitrile. Quantitative analysis of the obtained filtrate confirmed that it contained 0.55 g of the target product (yield 88.1%).

[0107] [Examples 3-2 to 3-3] Preparation of compound (3-1) 0.21 g of Raney nickel (manufactured by Tokyo Chemical Industry Co., Ltd., Skeletal Nickel Catalyst slowly in Water [Active Catalyst for Hydrogenation]) was weighed and washed with methanol (1 mL x 3 times). 14.4 g of methanol, 1.0 g of 28% by mass aqueous ammonia solution and 0.85 g of compound (2-1) were added to the residue. The resulting mixture was stirred at 25°C for 7 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the Raney nickel, and the filtrate was washed with methanol. Quantitative analysis of the obtained filtrate confirmed that it contained 0.71 g of the target product (yield 84.9%).

[0108] Furthermore, the reaction was carried out under the same conditions as described above, except for changes in the amount of Raney nickel used and the reaction time. The amount of Raney nickel used, reaction time, and yield are shown in Table 3 below.

[0109]

[0110] [Examples 3-4 to 3-5] The reaction was carried out under the same conditions as in Example 3-2, except that the manufacturing solvent and reaction time of compound (3-1) were changed. After the reaction was complete, the reaction mixture was filtered through Celite to remove Raney nickel, and the filtrate was washed with the reaction solvent and 35% by mass hydrochloric acid. The obtained filtrate was then quantitatively analyzed. The solvent, reaction time, and yield are listed in Table 4 below.

[0111]

[0112] [Examples 3-6 to 3-7] The reaction was carried out under the same conditions as in Example 3-2, except that the reaction temperature and reaction time for compound (3-1) were changed. After the reaction was complete, the reaction mixture was filtered through Celite to remove Raney nickel, and the filtrate was washed with the reaction solvent and 35% by mass hydrochloric acid. The obtained filtrate was then quantitatively analyzed. The solvent, reaction time, and yield are listed in Table 5 below.

[0113]

[0114] [Example 3-8] Preparation of compound (3-1) 0.21 g of Raney nickel (manufactured by Tokyo Chemical Industry Co., Ltd., Skeletal Nickel Catalyst slowly in Water [Active Catalyst for Hydrogenation]) was weighed and washed with methanol (1 mL x 3 times). 14.4 g of methanol, 1.26 g of ammonium acetate, 1.36 g of 48% by mass NaOH aqueous solution, and 0.84 g of compound (2-1) were added to the residue. After the addition was complete, the resulting mixture was stirred at 25°C for 30 hours under a hydrogen atmosphere at atmospheric pressure. After the reaction was complete, the reaction mixture was filtered through Celite to remove the Raney nickel, and the filtrate was washed with methanol and 35% by mass hydrochloric acid. Quantitative analysis of the obtained filtrate confirmed that it contained 0.78 g of the target product (yield 94.2%).

[0115] [Reference Examples 1-1 to 1-2] Preparation of 2,1-benzoisoxazole (hereinafter referred to as compound (4-1)) 1.00 g of 2-nitrobenzaldehyde (hereinafter referred to as compound (5-1)), 2.1 g of sodium hypophosphate monohydrate, 2.5 g of toluene, 2.5 g of water, and 0.69 g of 35% by mass hydrochloric acid were mixed with 0.005 g of 5% by mass palladium carbon ("Pd / C", manufactured by N.E. Chemcat, STD type, approximately 50% water content). After the addition was complete, the resulting reaction mixture was stirred at 60°C under a nitrogen atmosphere for 6 hours. After the reaction was complete, the reaction mixture was filtered through Celite to remove the palladium carbon, and the filtrate was washed with toluene. The resulting filtrate was separated, and the organic layer was quantitatively analyzed, confirming that it contained 0.75 g of the target substance (yield 93.6%).

[0116] Furthermore, the reaction was carried out under the same conditions as described above, except for a change in the type of acid. The type of acid, the amount of acid used [1.0 equivalent per compound (5-1)], and the yield are shown in Table 6 below.

[0117]

[0118] [Reference Example 2-1] Preparation of Compound (2-1) 1.19 g of 95% by mass sodium trifluoromethylsulfinate, 0.089 g of anhydrous iron(II) chloride, and 6.02 g of N,N-dimethylacetamide were added, and the mixture was heated to 80°C under a nitrogen atmosphere. To this reaction mixture, a mixture of 0.80 g of Compound (4-1) and 0.80 g of toluene was added over 30 minutes. After the addition was complete, the mixture was stirred at the same temperature for 2 hours. After the reaction was complete, the resulting reaction mixture was diluted with acetonitrile and 1 mol / L hydrochloric acid. Quantitative analysis of the resulting solution confirmed that it contained 1.55 g of the target substance (yield 91.2%).

[0119] [Reference Example 2-2] Preparation of Compound (2-1) 70.9 g of 95% by mass sodium trifluoromethylsulfinate, 1.88 g of iron(II) chloride tetrahydrate, and 338 g of N,N-dimethylacetamide were added, and the mixture was heated to 65°C under a nitrogen atmosphere. To this reaction mixture, a mixture of 45.0 g of compound (4-1) and 45.9 g of toluene was added over 30 minutes. After the addition was complete, the mixture was stirred at the same temperature for 2 hours. After the reaction was complete, the solvent was removed under reduced pressure. 360 g of toluene, 78.7 g of 35% by mass hydrochloric acid, and 270 g of water were added to the residue, and the mixture was separated. The resulting organic layer was washed with 11.8 g of 35% by mass hydrochloric acid and 270 g of water, and then washed with 270 g of water. Quantitative analysis of the resulting solution confirmed that it contained 86.3 g of the target substance (yield 90.2%).

[0120] [Reference Examples 2-3 to 2-6] Compound (2-1) was prepared by adding 0.30 g of compound (4-1), 0.41 g of 95% by mass sodium trifluoromethylsulfinate, 0.032 g of anhydrous iron(II) chloride, and 1.50 g of N,N-dimethylacetamide. The reaction mixture was heated to 80°C under a nitrogen atmosphere and stirred for 4 hours. After the reaction was complete, the resulting reaction mixture was diluted with acetonitrile and 1 mol / L hydrochloric acid. Quantitative analysis of the resulting solution confirmed that it contained 0.45 g of the target substance (yield 70.5%).

[0121] The reaction was carried out under the same conditions as described above, except for changes in the reaction solvent and reaction time. The reaction solvent, reaction time, and yield are shown in Table 7 below.

[0122]

[0123] [Reference Example 2-7] Compound (2-1) was prepared by adding 0.30 g of compound (4-1), 0.45 g of 95% by mass potassium trifluoromethylsulfinate, 0.032 g of anhydrous iron(II) chloride, and 1.50 g of N,N-dimethylacetamide. The reaction mixture was heated to 80°C under a nitrogen atmosphere and stirred for 2 hours. After the reaction was complete, the resulting reaction mixture was diluted with acetonitrile and 1 mol / L hydrochloric acid. Quantitative analysis of the resulting solution confirmed that it contained 0.49 g of the target substance (yield 76.1%).

[0124] [Reference Example 2-8] Preparation of Compound (2-1) 1.51 g of 65% by mass sodium trifluoromethylsulfinate and 5 g of 2-propanol were mixed, and the solid was filtered. The obtained filtrate was concentrated and dried under reduced pressure to obtain 1.08 g of solid. To the obtained solid, 0.053 g of anhydrous iron(II) chloride and 3.76 g of N,N-dimethylacetamide were added, and the mixture was heated to 65°C under a nitrogen atmosphere. To the reaction mixture, a mixture of 0.50 g of compound (4-1) and 0.52 g of toluene was added over 1 minute. After stirring at the same temperature for 8 hours, the temperature was raised to 80°C and the mixture was stirred for 1.5 hours. After the reaction was complete, quantitative analysis of the obtained solution confirmed that it contained 0.88 g of the target substance (yield 83.3%).

[0125] <Test Examples> Next, the usefulness of compound (1) of the present invention as a herbicide will be specifically explained in the following test examples, but the present invention is not limited to these.

[0126] [Test Example 1] Herbicide Efficacy Test by Foliar Treatment Alluvial soil was placed in a 1 / 10000 are Wagner pot, then water was added and mixed to a water depth of 0.1 to 0.5 cm. Seeds of barnyard grass, sedge grass, sedge grass, and rice were sown, and the plants were grown in a greenhouse at 25 to 30°C. After 14 days of growth, an emulsion containing compound (1-1) prepared according to Formulation Example 1 and an emulsion containing compound (1-2) prepared according to Formulation Example 1 were diluted with water to the specified dosage, and the stems and leaves were uniformly treated with a small spray. Two weeks after chemical treatment, the effects on each plant were investigated according to the following criteria. The results are shown in Table 8.

[0127] <Judgment Criteria> 5... Weed killing rate of 90% or more (almost complete death) 4... Weed killing rate of 70% or more but less than 90% 3... Weed killing rate of 40% or more but less than 70% 2... Weed killing rate of 20% or more but less than 40% 1... Weed killing rate of 5% or more but less than 20% 0... Weed killing rate of less than 5% (almost no effect)

[0128] [Test Example 2] Herbicide Efficacy Test by Foliar Treatment Sterilized alluvial soil was placed in a plastic box measuring 21 cm long, 13 cm wide, and 7 cm deep. Seeds of Japanese yew, Amaranthus philoxeroides, Laurel's cogongrass, Chickweed, Galium aparine, Veronica persica, Corn, Soybean, Rice, Wheat, Sugar beet, and Rapeseed were sown in spots, covered with approximately 1.5 cm of soil, and then grown in a greenhouse at 25 to 30°C. After 14 days of growth, an emulsion containing compound (1-1) prepared according to Formulation Example 1 and an emulsion containing compound (1-2) prepared according to Formulation Example 1 were diluted with water to the specified dosage and uniformly applied to the stems and leaves using a small spray. Two weeks after chemical treatment, the effects on each plant were investigated according to the criteria for Test Example 1. The results are shown in Table 9.

[0129] The symbols in Tables 8 through 9 represent the following: A: Barnyard grass, B: Grass, C: Cyperus rotundus, D: Japanese buckwheat, E: Amaranthus philoxeroides, F: Laurel, G: Chickweed, H: Galium aparine, I: Veronica persica, a: Rice, b: Corn, c: Soybean, d: Wheat, e: Beet, f: Rapeseed

[0130] Furthermore, the processing amount (g / ha) indicates that the concentration has been adjusted so that the specified number of grams (g) is processed per hectare (ha).

[0131]

[0132]

[0133] [Test Example 3] Tomato Ring Spot Disease Mycelial Growth Inhibition Test A potato glucose agar medium was prepared with a test agent concentration of 300 ppm. A colony of tomato ring spot disease fungus (Alternaria solani) was punched out using a cork borer (inner diameter φ4 mm), and the punched colonies were placed face down on the prepared agar medium. The medium was then incubated in the dark at 20°C for 3 days. Afterward, the mycelial growth length (mm) was measured from the colonies formed on the medium, and the mycelial growth inhibition rate was calculated according to the following formula: Mycelial growth inhibition rate = (Mycelial growth length without test agent - Mycelial growth length with test agent) / Mycelial growth length without test agent × 100

[0134] As a result, compounds (1-1) and (1-2) used as test agents both showed a mycelial growth inhibition rate of 70% or more.

[0135] [Test Example 4] Test to inhibit the growth of mycelium of onion gray rot fungus. A potato glucose agar medium was prepared so that the test agent was at 300 ppm. A colony of onion gray rot fungus (Botrytis allii) was punched out using a cork borer (inner diameter φ4 mm), and the punched colonies were placed on the prepared agar medium with the colony side down. The medium was incubated in the dark at 20°C for 3 days. After that, the mycelial growth length (mm) was measured from the colonies formed on the medium, and the mycelial growth inhibition rate was calculated using the same formula as in Test Example 3.

[0136] As a result, compounds (1-1) and (1-2) used as test agents both showed a mycelial growth inhibition rate of 70% or more.

[0137] [Test Example 5] Test to inhibit the growth of mycelium of peach gray mold fungus A potato glucose agar medium was prepared so that the test agent was at 300 ppm. A colony of peach gray mold fungus (Monilinia fructicola) was punched out with a cork borer (inner diameter φ4 mm), and the punched colonies were placed on the prepared agar medium with the colony side facing down and incubated in the dark at 20°C for 3 days. After that, the mycelial growth length (mm) was measured from the colonies formed on the medium, and the mycelial growth inhibition rate was calculated using the same formula as in Test Example 3.

[0138] As a result, compounds (1-1) and (1-2) used as test agents both showed a mycelial growth inhibition rate of 70% or more.

[0139] The trifluoromethanesulfonamide compounds of the present invention are novel compounds and are extremely useful as herbicides and fungicides.

Claims

1. Formula (1): [In the formula, M represents a hydrogen atom or C １ to C ６ alkyl] a trifluoromethanesulfonanilide compound represented by or a salt thereof.

2. The trifluoromethanesulfon anilide compound or salt thereof according to claim 1, wherein M is a hydrogen atom or a methyl atom.

3. Formula (2): A compound represented by or a salt thereof is dissolved in a solvent with hydroxylamine or C １ ~C ６ When reacted with an alkoxyamine having an alkoxy group, formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by [representing alkyl].

4. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 3, wherein the solvent comprises at least one of water, toluene, and methanol.

5. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 3 or 4, wherein the reaction is carried out in the presence of a base.

6. Formula (1): [In the formula, M is a hydrogen atom or C １ ~C ６ A trifluoromethanesulfonanilide compound or a salt thereof, represented by [representing alkyl], is reduced in a hydrogen atmosphere in the presence of a catalyst to obtain formula (3): A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by [formula].

7. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 6, wherein the catalyst comprises at least one of Raney nickel, palladium, and platinum.

8. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 6 or 7, further comprising adding an acid to carry out the reduction.

9. The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 8, wherein the acid is selected from the group consisting of acetic acid, hydrochloric acid, and sulfuric acid.

10. A method for producing a trifluoromethanesulfonanilide compound or salt thereof according to claim 6 or 7, wherein the amount of catalyst used is 0.0001 to 0.8 equivalents per equivalent of the trifluoromethanesulfonanilide compound or salt thereof represented by formula (1).

11. The method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 6 or 7, wherein the hydrogen atmosphere is further pressurized.

12. Formula (2): The compound represented by is reacted with ammonia in the presence of a catalyst containing at least one of Raney nickel, palladium, and platinum, and the resulting reaction product is further reduced in a hydrogen atmosphere to obtain formula (3): A method for producing a trifluoromethanesulfonanilide compound or a salt thereof, characterized by producing a trifluoromethanesulfonanilide compound or a salt thereof represented by [formula].

13. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 12, comprising reducing the compound in a hydrogen atmosphere under normal pressure.

14. A method for producing a trifluoromethanesulfonanilide compound or a salt thereof according to claim 12 or 13, comprising reacting a compound represented by formula (2) with 5 equivalents or less of ammonia.

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