JPH0479339B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula (): (In the formula, X represents a halogen atom; R represents a lower alkyl group; a lower haloalkyl group; a cycloalkyl group; a phenyl group or a benzyl group; n represents an integer from 0 to 2; R ₁ represents a hydrogen atom; an alkali metal Atom; ammonium salt; alkyl group having 1 to 6 carbon atoms; lower haloalkyl group; cycloalkyl group; cyanoalkyl group; alkenyl group; alkynyl group; lower alkoxyalkyl group; lower alkylthioalkyl group; lower alkoxyalkoxyalkyl group; hydroxy carbonylalkyl group; lower alkoxycarbonylalkyl group; phenyl group; benzyl group which may be substituted with a halogen atom or lower alkyl group; phenoxyalkyl group; phenethyl group; tetrahydrofurfuryl group) , 2,4-triazolin-5-one derivatives, their production methods, and herbicides. The present inventors have discovered that the compound represented by the above general formula () is a compound useful as an agricultural drug, especially a herbicide. The compound of the present invention is a novel compound described at the end of the literature. Surprisingly, the present invention was completed by discovering that the compound of the present invention exhibits an excellent herbicidal effect at a low dose and has little phytotoxicity to crops. Examples of methods for producing the compound represented by the general formula () of the present invention include the methods shown below. (In the formula, X, R, R ₁ , n and Z are the same as above.) That is, the compound represented by the general formula () is
Compounds represented by general formula () and general formula ()
It can be obtained by reacting the compound represented by in the presence of an inert solvent. The inert solvent used in this reaction may be any solvent as long as it does not significantly inhibit the progress of this type of reaction, such as aromatic hydrocarbons such as benzene, toluene, and xylene, and aliphatic solvents such as n-hexane and cyclohexane. Hydrocarbons, alcohols such as methanol, ethanol, propanol, and glycol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, lower fatty acid esters such as ethyl acetate, ethers such as tetrahydrofuran and dioxane, dimethylformamide, dimethylacetamide, etc. Examples include lower fatty acid amides, water, dimethyl sulfoxide, and the like. These solvents are used alone or in mixtures. Bases that can be used in this reaction include:
Inorganic bases such as sodium carbonate, sodium hydride, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydroxide, potassium hydroxide and alcoholates of alkali metals, pyridine, trimethylamine, triethylamine, diethylaniline, 1,8-diazabicyclo −[5,
Organic bases such as 4,0]-7-undecene can be mentioned. The reaction of the present invention can be allowed to proceed at an appropriately determined temperature within the range of, for example, 0°C to 150°C. The reactions of the compounds in each reaction route are equimolar reactions, but it is okay to add one or the other in slightly excess. The reaction time is preferably selected from the range of 0.5 to 48 hours. After the reaction is completed, the target product can be collected by treating the reaction product in a conventional manner. Moreover, the compound represented by the general formula () can also be produced by the method shown below. (In the formula, X, R and R ₁ are the same as above.) That is, the compound represented by the general formula (-a) is the same as the compound represented by the general formula (-a) and R ₁
It can also be produced by reacting with a corresponding alcohol and esterifying it. A compound represented by the general formula () where n=1 or 2 can also be produced by oxidizing a corresponding compound where n=0 with a suitable oxidizing agent. Representative examples of the compounds represented by the general formula () are shown in Table 1 below.

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[Table] The compound represented by the general formula () can be synthesized by the following reaction route. (In the formula, X is the same as above, R ² and R ³ represent a lower alkyl group, Z represents a halogen atom, and A
represents an oxygen atom or a sulfur atom. ) That is, the compound represented by the general formula () is
Compounds represented by general formula () and general formula ()
A compound represented by the formula () is reacted with heating in an inert solvent, and the resulting compound represented by the general formula () is isolated, or without isolation, a ring-closing reaction is performed in the presence of a base to form the compound represented by the general formula ( ), reacting the compound () with a halide represented by the general formula () to obtain a compound represented by the general formula (), and reacting the compound () with hydrogen bromide to form the compound represented by the general formula A compound represented by () can be obtained. Note that when producing the compound represented by the general formula () from the compound represented by the general formula (), hydrogen iodide or an alkylthiolate may be used instead of hydrogen bromide. Examples of the present invention are shown below, but the present invention is not limited thereto. Example 1 Methyl α-[2-chloro-5-(4-
Difluoromethyl-3-methyl-Δ ² -triazolin-5-one-1-yl)-4-fluorophenoxy]α-methylthioacetate (Compound No.
35) 249g of 1-(4-chloro-2-fluoro-5-
hydroxyphenyl)-4-difluoromethyl-
3-Methyl-Δ ² -1,2,4-triazoline-
5-one, 1.35 g (0.011 mol) of methyl α-chloro-α-methylthioacetate and 2.94 g of K ₂ CO ₃
Suspend in 50 ml of acetone and heat under reflux for 3 hours.
After the reaction is completed, the reaction solution is cooled to room temperature, insoluble matter is removed, and acetone is distilled off to obtain an oily substance. The obtained oil is purified by dry column chromatography to obtain 3.5 g of the desired product. n ²⁶ _D 1.5357 Yield 92.1% Example 2 3-chloropropyl α-[2,4-
Dichloro-5-(4-difluoromethyl-3-methyl-Δ ² -1,2,4-triazolin-5-one-1-yl)phenoxy]-α-isopropylthioacetate (Compound No. 71) 0.52 g (3.7 mmol) of potassium carbonate in 50 ml of N,
Suspended in N-dimethylformamide, 1-(2,4-dichloro-4-hydroxyphenyl)-3-methyl-4-difluoromethyl- ^{Δ 2}
-1,2,4-triazolin-5-one 1.18g
(0.034 mol) and stirred at room temperature for 30 minutes, then 1.1 g (0.0034 mol) of 3-chloropropyl α-bromo-α-isopropylthioacetate was added.
The reaction was carried out at 50°C for 3 hours. After the reaction was completed, the reaction solution was brought to room temperature, poured into ice water, and the product was extracted with diethyl ether. After washing the extract with water and drying, diethyl ether was distilled off to obtain the desired product. n ²⁵ _D 1.5377 Yield 89% Example 3 4-chlorobenzyl α-[2-chloro-5-(4-difluoromethyl-3-methyl-
Δ ² -1,2,4-triazolin-5-one-1
-yl)-4-fluorophenoxy]-α-methylthioacetate (Compound No. 45) 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-difluoromethyl-Δ ² -1,2,4-triazolin-5-one 1.5 g (0.0051 mol), potassium carbonate 1.5g and 4-
1.73 g (0.0056 mol) of chlorobenzyl α-bromo-α-methylthioacetate was added to 50 ml of methyl ethyl ketone, and the mixture was heated under reflux for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, insoluble materials were separated, the solution was concentrated, and the residue was purified by dry column chromatography to obtain the desired product. n ²⁵ _D 1.5601 Yield 72% Example 4 Sodium α-[2.4-dichloro-5-
(4-difluoromethyl-3-methyl-Δ ² −1.24
-Triazolin-5-one-1-yl)phenoxy]-α-difluoromethylthioacetate (Compound No. 112) 0.45 g (0.001 mol) of α-[2,4-dichloro-5
-(4-difluoromethyl-3-methyl-Δ ² -
0.04 g of 1.24-triazolin-5-on-1-yl)phenoxy]-α-difluoromethylthioacetic acid
The mixture was added to 30 ml of methanol solution containing (0.001 mol) of NaOH and stirred for 30 minutes. After the reaction is complete, methanol is distilled off, and the resulting crystals are washed with ether and dried to obtain 0.45 g of the desired product. m・p＞250℃ Yield 95.7% Example 5 Methyl α-[2.4-dichloro-5-
(4-difluoromethyl-3-methyl-Δ ² -1,
2,4-triazolin-5-one-1-yl)phenoxy]-α-phenylsulfinyl acetate (Compound No. 129) 2.4 g (0.005 mol) of methyl α-[2,4-dichloro-5-(4-difluoromethyl-3-methyl- ^{Δ 2} -1,2,4-triazolin-5-one-
1-yl)-phenoxy]-α-phenylthioacetate was dissolved in 50 ml of dichloromethane and stirred at room temperature.
After adding 0.94 g (0.0055 mol) of metachloroperbenzoic acid and reacting for 6 hours, the product was poured into water.
Extract with ether and process in a conventional manner to obtain 2.1 g of the desired product. mp142.8℃ Yield 84% Example 6 Ethyl α-[2-chloro-5-(4-
Difluoromethyl-3-methyl-Δ ² -1,2,
4-triazolin-5-one-1-yl)-4-
Fluorophenyl]-α-methylsulfonylacetate (Compound No. 130) 4.26 g (0.01 mol) of ethyl α-[2-chloro-
5-(4-difluoromethyl-3-methyl-Δ ² −
Dissolve 1,2,4-triazolin-5-one-1-yl)-4-fluorophenoxy]-α-methylthioacetate in 70 ml of dichloromethane and add 3.78 g (0.022 mol) of metachloroperbenzoic acid at room temperature. was added and the reaction was carried out for 6 hours. After the reaction is completed, the reaction product is poured into water, the dichloromethane layer is separated, and the mixture is treated in a conventional manner to obtain 4.1 g of the desired product. n ²⁵ _D 1.5238 Yield 89.7% 1,2,4 represented by the general formula () of the present invention
-Triazolin-5-one derivatives are used, for example, in the grass field (a common name for Japanese field grass. An annual grass of the Poaceae family. A typical harmful grass of paddy fields) and Konagi (an annual grass of the Poaceae family).
A harmful grass of paddy fields), Cyperus japonica (an annual grass of the Cyperaceae family, a harmful grass of rice fields), Matsubai (a perennial grass of the Cyperaceae family, which occurs in wetlands, waterways, and rice fields. A typical perennial harmful grass of rice fields), Urikawa (family Cyperaceae). annual and perennial weeds in paddy fields such as bulrush (a perennial grass of the Cyperaceae family, which occurs in rice fields, wetlands, and ditches); ), Mugwort (a perennial grass of the Asteraceae family. Occurs in fields and fields), Mugwort (an annual grass of the Poaceae family, a typical harmful grass in fields and remote areas), Gishigishi (a perennial grass of the Polygonaceae family. Occurs in fields and roadsides) , Cyperaceae (Cyperaceae 1)
Occurs in fields and orchards, such as annual grasses, fields, and roadsides), Aobiyu (an annual grass in the barnyard family, which occurs in vacant lots, roadsides, and fields), and Japanese staghorn (an annual grass, in the Asteraceae family, which is a strong soybean plant). It has the effect of controlling annual and perennial weeds. Triazoline represented by the above general formula ()
Since 5-one derivatives exhibit excellent herbicidal activity against weeds before emergence and during the growing season, they can be used for sowing (planting) of field crops such as soybeans, cotton, and corn.
The compound of the present invention is useful as a herbicide for pre-soil treatment, post-sowing (planting) soil treatment, soil treatment during the crop growing season, foliage treatment before crop sowing (planting), and foliage treatment during the crop growing season. It is useful as a medium-term herbicide and also as a weed killer for general weeds, such as mowing remains, fallow fields, ridges, farm roads, waterways, pasture land, cemeteries, parks, roads, playgrounds, open spaces around buildings, cleared land, and railroad tracks. It can also be used to exterminate common weeds in forests, etc. In this case, it is economically most effective to treat weeds before they begin to emerge, but this is not necessarily the case. By the way, when the compound of the present invention is used as a herbicide, it is generally formulated into a convenient form for use in accordance with the conventional method for planting pesticide formulations. That is, the above compound can be dissolved, separated, suspended, mixed, impregnated, etc. by blending it with a suitable inert carrier in an appropriate proportion together with an auxiliary agent if necessary.
It is advisable to adsorb or adhere the compound and formulate it into an appropriate dosage form, such as a suspension, emulsion, solution, wettable powder, powder, granule, or tablet. The inert carrier that can be used in the present invention may be either solid or liquid, and examples of materials that can be solid carriers include soybean flour,
Vegetable powders such as grain flour, wood flour, bark powder, saw flour, tobacco stem powder, walnut flour, bran, cellulose powder, and residues of plant extract extraction; textile products such as paper and cardboard boxes and furugiri; pulverized synthesis Synthetic polymers such as resins;
Clays (e.g. kaolin, bentonite, acid clay), talcs (e.g. talc, hylofilite), silicas (e.g. diatomaceous earth, silica sand, mica, white carbon [synthetic highly dispersed silicic acid, also called hydrated differential silica or hydrated silicic acid; Some products contain calcium silicate as a main component]), activated carbon,
Sulfur powder, pumice, calcined diatomaceous earth, crushed bricks,
Inorganic mineral powders such as fly ash, sand, calcium carbonate, calcium phosphate; ammonium sulfate, ammonium phosphorus, ammonium nitrate,
Examples include chemical fertilizers such as urea and ammonium chloride, and compost. These may be used alone or in a mixture of two or more. Materials that can serve as liquid carriers include those that themselves have solvent ability;
They are selected from those that enable the active ingredient compound to be dispersed with the help of an adjuvant even without solvent ability, such as the following, which may be used alone or in the form of a mixture of two or more. ru; water;
Alcohols (e.g. methanol, ethanol,
isopropanol, butanol, ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone), ethers (e.g. ethyl ether, dioxane, cellosolve,
dipropyl ether, tetrahydrofuran), aliphatic hydrocarbons (e.g. gasoline, mineral oil), aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha, alkylnaphthalene),
halogenated hydrocarbons (e.g. dichloroethane,
chlorinated benzene, chloroform, carbon tetrachloride),
Esters (e.g. ethyl acetate, dibutyl phthalate, diisopropyl phthalate, dioctyl phthalate), acid amides (e.g. dimethylformamide, diethylformamide, dimethylacetamide), nitriles (e.g. acetonitrile),
Dimethyl sulfoxide etc. The following may be mentioned as adjuvants. These adjuvants are used depending on the purpose.
In some cases, two or more adjuvants are used together. In other cases, no adjuvant may be used at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing or wetting the active ingredient compounds. Examples include: polyoxyethylene, furkylaryl ether, polyoxyethylene, alkyl ether, polyoxyethylene, higher fatty acid ester, polyoxyethylene,
Resin acid ester, polyoxyethylene, sorbitan monolaurate, polyoxyethylene, sorbitan monooleate, alkylaryl, sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, higher alcohol sulfate, etc.
For the purpose of dispersion stabilization, adhesion or binding of the active ingredient compounds, the following may be used, for example: casein, gelatin, starch, alginic acid, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil, Sugar oil, bentonite, lignin sulfonate, etc. For the purpose of improving the flow of solid products, the following may also be used: waxes, etc., stearates, phosphoric acid alkyl esters, etc. The following may also be used as peptizers for suspendable products: naphthalene sulfonic acid condensates, condensed phosphates, etc. It is also possible to add antifoaming agents such as silicone oil. The combination of active ingredients can be adjusted as necessary. Usually 0.5 to 20% (by weight) when used as a powder or granule, and 0.1 to 20% (by weight) when used as an emulsion or wettable powder.
50% (by weight) is appropriate. The herbicide of the present invention can be used as it is, or in an appropriately diluted or suspended form with water, etc., to kill or suppress the growth of various weeds, or to protect useful plants from weed damage. An effective amount is applied to the weeds or to the foliage or soil in locations where the emergence or growth of the weeds is unfavorable. The amount of the herbicide of the present invention to be used depends on various factors, such as the purpose, target weeds, weed or crop emergence/growth conditions, weed emergence trends, weather, environmental conditions, dosage form, application method, application location, and application time. It changes over time. When the herbicide of the present invention is used alone as a selective herbicide, it is appropriate to select the dosage of the compound of the present invention from 0.1 to 500 g per 10 ares, for example.
When the herbicide of the present invention is used in combination with other herbicides, the dosage of the compound of the present invention is often lower, considering that it is effective at a lower dose than when used alone. It is also possible to select from a range. The herbicide of the present invention is particularly valuable as a treatment agent from before the emergence of weeds in field crops to the growing season, or as an early to mid-stage herbicide in paddy fields. It is also possible to use it in combination with other herbicides in order to reduce the amount of herbicides, and this falls within the scope of the present invention. For example, phenoxy fatty acid herbicides such as 2,4-PA (e.g. 2,4
-ethyl dichlorophenoxyacetate), MCP (e.g. ethyl 2-methyl-4-chlorophenoxyacetate, sodium 2-methyl-4-chlorophenoxyacetate, allyl 2-methyl-4-chlorophenoxyacetate), MCPB (ethyl 2-methyl-4-chlorophenoxyacetate), Diphenyl ether herbicides such as NIP (2,4-dichlorophenoxy-ethyl acetate), dichlohopmethyl (methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate) phenyl ether), CNP (2,4,
6-trichlorophenyl-4'-nitrophenyl ether), chromethoxynil (2,4-dichlorophenyl-3'-methoxy-4'-nitrophenyl ether), acifluorfen (5-(2-chloro-α) , α,α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid and its salts), fluadihop-butyl-((±)-2[4-
[[5-(trifluoromethyl)-2-pyridyl]oxy]phenoxy]propionic acid butyl ester); triazine herbicides such as CAT [2-chloro-4,6-bis(ethylamino)-s-triazine], Promethrin [2-methylthio-4,6
-bis(isopropylamino)-s-triazine], cymetrine [2-methylthio-4,6-bis(ethylamino)-s-triazine], metribuzine (4-amino-6-t-butyl-3-methylthio-1 , 2,4-triazin-5(4H)-one); carbamate herbicides such as molinate (s-ethylhexahydro-1H-azevin-1-
carbothioate), MCC [methyl N-(3,4-
dichlorophenyl)-carbamate], IPC [isopropyl N-(3-chlorophenyl)carbamate], benticaobe [s-(4-chlorobenzyl) dimethylthiocarbamate]; toluidine herbicides such as trifluralin (α,α,α-trifluoro- 2,6-dinitro-N,N-diprovir-p-toluidine), benzimesaline (N-(1
-ethylpropyl)-2,6-dinitro-3,4
-xylidine); acid amide herbicides such as DCPA
(3,4-dichloropropionanilide), ptachlor [2-chloro-2',6'-diethyl-N-
(butoxymethyl)-acetanilide], alachlor [2-chloro-2',6'-diethyl-N-(methoxyethyl)acetanilide], metolachlor (2-chloro-N(2-ethyl-6-methylphenyl)- N-(2-methoxy-1-methylethyl)acetamide), pretilachlor (2-chloro-2',6'-diethyl-N-(2-propoxyethyl)acetanilide); other herbicides e.g.
DCMU (3-(3,4-dichlorophenyl)1,
1-dimethylurea), bentazone (3-isopropyl-(1H)-2,1,3-benzothiadiazin-4(3H)-one 22-dioxide, pyrazolate (4-(2,4-dichlorobenzoyl) -1,
3-dimethylpyrazol-5-yl-p-toluninsulfonate, pyrazoxyphene (1,3-dimethyl-4(2,4-dichlorobenzoyl)-5-
Phenacyloxypyrazole, MY-71 (4-
(2,4-dichloro-3-methylbenzoyl)-
An embodiment may be mentioned in which it is mixed with one or more herbicides such as 1,3-dimethylpyrazol-5-yl-p-toluenesulfonate. Some test examples and formulations are shown below, but the present invention is not limited thereto. Test example 1: Effect on paddy field weeds before budding Fill a 1/10,000th R pot with soil, make it into a paddy field, and treat the paddy field weeds such as field weeds, Japanese grasshopper, Japanese cypress, firefly seeds, and urikawa tubers before budding. It was adjusted. This was treated with active ingredients (compounds listed in Table 1) as a spray solution at a predetermined concentration. The herbicidal effects of each treatment were compared with those without treatment after 21 days of treatment, and judgments were made based on the following criteria. Judgment criteria for herbicidal activity 5...100% weed killing 4...90% to less than 100% weed killing 3...80% to less than 90% weed killing 2...70% to less than 80% weed killing 1...less than 70% weed killing Shown in Table 2.

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[Table] Test Example 2: Effect on paddy field weeds after germination Soil was put into a 1/10,000-are pot, and the noxious weeds in the following leaf stages were grown in a paddy field condition. Furthermore, the day before the chemical treatment, paddy rice seedlings (variety: Nipponbare) at the 2nd and 5th leaf stage were transplanted and treated with the chemical. 21 days after the treatment, the herbicidal effect and the degree of chemical damage to paddy rice were investigated in comparison with no treatment. Tested weed species and their leaf stages: Japanese grasshopper, 1-leaf stage, Konagi, 2-3-leaf stage, Cyperus 1-2-leaf stage, Hotaru, 2-3-leaf stage, Urhikawa, 3-leaf stage, Cyperus japonica, 1-2 leaf stage Judgment criteria for chemical damage H ...Large (including withering) M...Medium L...Small N...No Criteria for determining herbicidal activity are in accordance with Test Example 1. The results are shown in Table 3.

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[Table] Test Example 3: Effect on upland weeds before they emerge Soil was packed in a polyethylene bucket measuring 10 cm x 20 cm x 5 cm deep, and upland weeds such as oat, wild grass, blackberry, blueberry, mugwort, staghorn grass, staghorn snail, and staghorn were removed. The seeds were sown and covered with soil. This was treated with the active ingredient after being sprayed at a predetermined concentration, and 21 days after the treatment, the herbicidal effects of each were investigated in comparison with the untreated condition. The criteria for determining herbicidal activity were in accordance with Test Example 1. The results are shown in Table 4.

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[Table] Test Example 4: Effect on field weeds after germination In a polyethylene vat measuring 10 cm x 20 cm x 5 cm deep, the noxious weeds and soybean seeds shown below were sown and covered with soil, and each was allowed to grow until it reached the lower leaf stage. The drug was processed to contain the active ingredient at a predetermined dose. 21 days after the treatment, the herbicidal effect and the degree of phytotoxicity on soybean were investigated in comparison with the untreated condition. Test weed species and their leaf stages, and soybean leaf stage Oat, 2-leaf stage, Black-seed grass, 2-leaf stage, Blueberry, 1-leaf stage, Artemisia, 1-leaf stage, Crested lily, 2-leaf stage, Kogomega spp., 1-leaf stage, Japanese fir tree, 1-leaf stage, Soybean, 1st compound-leaf stage Judgment criteria for herbicidal activity and the criteria for determining drug damage were in accordance with Test Examples 1 and 2, respectively. The results are shown in Table 5.

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[Table] Formulation example 1 Compound No. 1 50 parts Clay/white carbon mixture mainly consisting of clay 45 parts Polyoxyethylene nonyl phenyl ether
A hydrating agent made by uniformly mixing and pulverizing 5 parts. Formulation example 2 Compound No. 7 5 parts Bentonite clay mixture 90 parts Calcium ligninsulfonate 5 parts are uniformly mixed and ground, and an appropriate amount of water is added, kneaded well, and granulated. Formulation Example 3 An emulsion made by uniformly mixing 50 parts of Compound No. 31, 40 parts of xylene, and 10 parts of a mixture of polyoxyethylene nonyl phenyl ether and calcium alkylbenzenesulfonate.

Claims (1)

[Claims] 1 General formula (): (In the formula, X represents a halogen atom; R represents a lower alkyl group; a lower haloalkyl group; a cycloalkyl group; a phenyl group or a benzyl group; _n represents an integer from 0 to 2; Metal atom; ammonium salt; alkyl group having 1 to 6 carbon atoms; lower haloalkyl group; cycloalkyl group; cyanoalkyl group; alkenyl group; alkynyl group; lower alkoxyalkyl group; lower alkylthioalkyl group; lower alkoxyalkoxyalkyl group; Hydroxycarbonylalkyl group; Lower alkoxycarbonylalkyl group; Phenyl group; Benzyl group which may be substituted with a halogen atom or lower alkyl group; Phenoxyalkyl group; Phenethyl group; Tetrahydrofurfuryl group) 1,2,4-triazolin-5-one derivative. 2 General formula (): (In the formula, X represents a halogen atom.) Compounds represented by and general formula (): (In the formula, R represents a lower alkyl group; a lower haloalkyl group; a cycloalkyl group; a phenyl group or a benzyl group; n represents an integer of 0 to 2; R ₁ is a hydrogen atom; an alkali metal atom; an ammonium salt;
Alkyl group having 1 to 6 carbon atoms; lower haloalkyl group; cycloalkyl group; cyanoalkyl group;
Alkenyl group; Alkynyl group; Lower alkoxyalkyl group; Lower alkylthioalkyl group; Lower alkoxyalkoxyalkyl group; Hydroxycarbonylalkyl group; Lower alkoxycarbonylalkyl group; Phenyl group; Benzyl group optionally substituted with a halogen atom or lower alkyl group ; phenoxyalkyl group; phenethyl group; tetrahydrofurfuryl group, and Z represents a halogen atom. ) A general formula () characterized by reacting a compound represented by: (In the formula, XRR ₁ and n are the same as above.) A method for producing a 1,2,4-triazolin-5-one derivative represented by: 3 General formula (): (In the formula, X represents a halogen atom; R represents a lower alkyl group; a lower haloalkyl group; a cycloalkyl group; a phenyl group or a benzyl group; n represents an integer from 0 to 2; R ₁ represents a hydrogen atom; an alkali metal Atom; ammonium salt; alkyl group having 1 to 6 carbon atoms; lower haloalkyl group; cycloalkyl group; cyanoalkyl group; alkenyl group; alkynyl group; lower alkoxyalkyl group; lower alkylthioalkyl group; lower alkoxyalkoxyalkyl group; hydroxy carbonylalkyl group; lower alkoxycarbonylalkyl group; phenyl group; benzyl group which may be substituted with a halogen atom or lower alkyl group; phenoxyalkyl group; phenethyl group; tetrahydrofurfuryl group) , 2,4-triazolin-5-one derivative as an active ingredient.