JPS63139174A - Delta2-1,2,4-triazolin-5-one derivative, its production and use thereof - Google Patents

Abstract

NEW MATERIAL:The DELTA<2>-1,2,4-triazolin-5-one derivative of formula I (R is halogenated alkyl, cycloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, benzyl, phenetyl, etc.; R<1> is haloethyl; X is halogen). EXAMPLE:1{2,4-Dichloro-5-[1-(3-chloropropoxycarbonyl)ethoxy]phenyl}-4- (1,1,2,2- tetrafluoroethyl)-3-methyl-DELTA<2>-1,2,4-triazolin-5-one. USE:A herbicide. PREPARATION:The compound of formula I can be produced by reacting a compound of formula II (X is halogen) with a compound of formula III (Z is halogen).

Description

Detailed Description of the Invention The present invention is based on the general formula (■): (However, in the formula, 几 is an alkyl group substituted with a halogen atom; a cycloargyl group; a cyanoalkyl group; an alkenyl group; an alkynyl group: a lower alkoxyalkyl group) lower alkylthioalkyl group; lower alkylsulfinyl alkyl group; lower alkylsulfonylalkyl group; hydroxycarbonyl alkyl group; lower alkoxycarbonyl alkyl group: benzyl group; benzyl group substituted with a halogen atom or lower alkyl group; R1 represents a haloethyl group, and X represents a halogen atom.) Δ2-1.2.4-triazoline-5-
This article relates to on derivatives, their cleavage methods, and their uses.

The present inventors have discovered that the compound represented by the above general formula (1) is a compound useful as an agricultural drug, especially a herbicide. JP-A-57-181069 discloses compounds similar to the compounds of the present invention as herbicides. However, the compound of the present invention has not been disclosed at all and is a new compound that has not been described in any literature.

Surprisingly, it has been discovered that the compound of the present invention exhibits a worrying herbicidal effect at a low dose and is less harmful to crops than the compound disclosed in the above-mentioned publication. It is a completed invention.

The compound represented by the general formula (1) of the present invention can be produced, for example, by the method shown below.

Base (I) (U (In the formula, R9 and X have the same meanings as above, and Z represents a halogen atom.) That is, the compound represented by the general formula (1) is a compound represented by the general formula (ff) P can be obtained by reacting the compound represented by the formula (1) with the compound represented by the general formula (1) in the presence of an inert solvent.

The inert solvent used in the reaction of the present invention may be any solvent that does not significantly inhibit the progress of this reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, n-hexane, cyclohexane, etc. Aliphatic hydrocarbons, alcohols such as methanol, ethanol, propatool, glycol, etc., acetone, methyl ethyl ketone,
Examples include ketones such as cyclohexanone, lower fatty acid esters such as ethyl acetate, ethers such as tetrahydrofuran and dioxane, lower fatty acid amides such as dimethylformamide and dimethylacetamide, water, and dimethyl sulfoxide.

These solvents are used alone or as a mixture.

Examples of bases that can be used in this reaction include inorganic bases such as sodium carbonate, sodium hydride, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydroxide, potassium hydroxide, and alkali metal alcoholades, pyridine, Triethylamine, triethylamine, diethylaniline, 1,8-diazabicyclo-[
Organic bases such as 5,4,0]-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 a little too much of either one.

The reaction time is preferably selected from the range of 15 to 48 hours.

After the reaction is completed, the target product can be collected by treating the reaction product in a conventional manner.

Further, the compound represented by the general formula (f) can also be produced in seconds according to the formula shown below.

(1-a) (1) (wherein, R
,, R1 and X have the same meanings as above, and R4 represents a hydroxyl group or a halogen atom. ) That is, general formula N-a)
It can also be obtained by reacting the compound represented by with the corresponding alcohol.

In addition, compounds represented by the general formula (1) in which R represents a lower alkylsulfinyl alkyl group or a lower alkylsulfonylalkyl group are compounds represented by the general formula (1) in which the corresponding R is a lower alkylthioalkyl group. It can also be obtained by oxidizing with a suitable oxidizing agent.

Representative examples of the compounds represented by the general formula (1) are shown in Table 1 as follows.

General formula (I): The compound represented by general formula (If) can be synthesized by the following reaction route.

A base (phantom (in the formula, El, Z and ) That is, the compound represented by the general formula (II) is obtained by reacting the compound represented by the general formula (X) with the compound represented by the general formula (1) in an inert solvent under heating. A compound represented by the formula (V) is isolated or not isolated, and a ring-closing reaction is carried out in the presence of a base to obtain a compound represented by the general formula (VID). ) by reacting halides represented by the general formula (
A compound represented by general formula (II) can be obtained by reacting the compound (IV) with hydrogen bromide.

When producing the compound represented by the general formula (1'V) from the compound represented by the general formula (1'V), hydrogen iodide or alkylthiolade 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 1-(2,4-dichloro-5-(1-(3-chloropropoxycarbonyl)ethoxy]phenyl)-4-(1
,1,2,2-tetrafluoroethyl)-6-methyl-
Δ2-1.2.4-) Riazolin-5-one (Compound 7) 1- (2,4-dichloro-5-hydroxyphenyl)
-3-Methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ2-1.2.4- )su7zoli:y-5-
Dissolve 1.8 g (0,0051 mol) of α-chloropropionic acid in 40 grams of anhydrous dimethyl sulfoxide, add 3 g (10,053 mol) of powdered potassium hydroxide, and stir for 30 minutes. -Chloropropyl ester 1. Ofl (α0053 mol) was added and 80
The reaction was carried out at ℃ for □4 hours. After the reaction was completed, the reaction solution was cooled 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 2.39f.

n" 1.5139 0 Yield 89% Example? 1-14-chloro-2-fluoro-5-(1-((3-
10lopropyl)carbonyl)ethoxy]phenyl
4 (1,1,2,2-tetrafluoroethyl-3
-Methyl-42-1,2,4-triazolin-5-one (compound A8) Potassium carbonate + 7A n, 52 g (0,
0037 mol) ts.

d in N,N-dimethylformamide, and to this suspension 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-71 thyl-4-(1,1,2,2- After adding 1.1719 ((10034 mol)) of liazolin-5-one ((tetrafluoroethyl)-Δ2-1.2.4-) and stirring at room temperature for 30 minutes, α-bromopropionic acid 3-diO.

Propyl ester [185 g (0,0034 mol) was added and 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 1.36 g of the desired product.

n241.4989 The obtained oil was purified by silica gel column chromatography (ether "n-hexane-1:2)" and when it was left to stand at room temperature, the desired product was obtained as crystals.

m,p,4a5℃ Yield 82% Example 5 l-(4-chloro-2-fluoro-5-[1-((2-
Ethylthio)ethoxycarbonyl)ethoxy]phenyl 4-(2-chloro-1゜1.2-)IJfluoroethyl)-3-methyl-Δ2 1,2.4-triazolin-5-one F'O 0.15g (0,0057 mol) of 60% NaH13
Suspended in 0 m tetrahydrofuran, this suspension VC
1-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-methyl-4-(2-chloro-1,1,2-
1-! J fluoroethyl)-Δ2-1.2.4- triazolin-5-one 1.26 g ([10034 mol)
was added and stirred for 30 minutes, then α-bromopropionic acid (2-
ethylthio) ethylnistil 0.8951 (10067
mol le was added at 5 o'clock)...The mixture was heated to reflux. After the reaction was completed, the reaction solution was cooled 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 and the residue was purified by dry column chromatography to obtain the desired product 1.639.

Yield 75% Example 4 l-(4-chloro-2-fluoro-5-[1-(4-chlorobenzyloxycarbonyl)ethoxy]phenyl)
4-(1,i,2,2-tetrafluoroethyl)-3-
,% ChiruΔ2-1゜2.4-triazolin-5-one (compound 60) (1-i3 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-(1 ,1゜2.2-tetrafluoroethyl)-Δ2-1.2゜4-driazoline-5
-ony 1.75 g (0,0051 mol), potassium carbonate 1.59 and α-bromopropionic acid 4-chlorobenzyl ester 1.279 (5.6 mmol) in 5
The mixture was added to 0+J of methyl ethyl ketone and heated under reflux for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the insoluble matter was filtered out, the e-liquid was concentrated, and the residue was purified by dry column chromatography to obtain 1.87 g of the desired product.

nD 1.5329 Yield 68% Example 5 1-i 2,4-dichloro-5-(1-(2-methylsulfinyl)ethoxy/carbonyl]-ethoxyphenyl)-5-methyl-4(1,1° 2.2-tetrafluoroethyl)-Δ2-1.2゜4-triazolin-5-one (compound 47)■ CH3 5.05g (0.01 mol) of 1-(2,4-dichloro-5- CI-(2-methylthio)-ethoxycarbonyl]-ethoxyphenyl)-3-methyl-4-(1,1,
2,2-tetrafluoroethyl)-Δ2-1.2.4-
Triazolin-5-one was dissolved in 100-methylene chloride, m of ';tag (0,0106 mol) and chloroperbenzoic acid were added, and the reaction was carried out at room temperature for 5 hours. The reaction mixture was poured into ice water and the chloride was dissolved. The methylene layer is treated in a conventional manner to obtain 48 g of the desired product.

n 'n' 1.5 ' 95 Yield 92.
1% Δ2-1.2 represented by the general formula (1) of the present invention,
4-triazolin-5-one derivatives are, for example,
Common name for Tainubie. An annual grass of the Poaceae family. Typical harmful grass of paddy fields), Konagi (annual grass of the family Chrysanthemum family. A very harmful grass of paddy fields)
, Cyperaceae (annual grass of the family Cyperaceae. Fragrant herb of paddy fields), Cyperus (perennial grass of the family Cyperaceae. Wetlands, waterways,
Occurs in rice fields. Typical perennial herb of paddy fields), Urikawa (family Omodacaceae. A perennial aromatic herb that grows in rice fields, wetlands, and ditches), Hotarui (perennial herb of Cyperaceae family).

annual and perennial weeds in paddy fields such as paddy fields, wetlands, and rice fields; oat (an perennial grass of the Poaceae family; occurs in plains, wastelands, and fields); mugwort (a perennial grass of the Asteraceae family);

Occurs in mountains, fields, and fields), Mehishiba (an annual grass of the Poaceae family, fields,
A typical harmful grass in orchards), Gishigishi (a perennial grass of the Polygonaceae family).

(occurs in fields and roadsides), cyperus (an annual grass of the family Cyperaceae, occurs in fields and roadsides), and cyperus (an annual grass of the family Cyperaceae).

It has the effect of controlling annual and perennial weeds that occur in fields and orchards, such as Asteraceae (an annual grass of the Asteraceae family, a plant that is highly harmful to soybeans).

The triazolin-5-one derivative represented by the above general formula (1) exhibits excellent herbicidal activity against weeds before emergence and during the growing season, so it can be used, for example, in 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 herbicide for general weeds, such as mowing remains, fallow fields, ridges, farm roads, waterways, pasture land, cemeteries, parks, roads, playgrounds, open spaces around buildings, cultivated land, etc. It can also be used to exterminate common weeds on railroad tracks, forests, etc. In this case, it is best to treat weeds before they begin to emerge.
Although it is economically the most effective, it is not necessary to be particular about it.

By the way, when the compound of the present invention is used as a herbicide, it is generally formulated into a form convenient for use according to the conventional method for preparing pickles.

That is, the above-mentioned compound is dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered to an appropriate inert carrier, together with an auxiliary agent if necessary, in an appropriate proportion, and then prepared into an appropriate dosage form. , such as suspensions, emulsions, solutions, aqueous preparations, powders,
It is recommended to formulate it into granules, tablets, etc.

The inert carrier that can be used in the present invention may be either solid or liquid, and materials that can be solid carriers include, for example, quiz flour, grain flour, water flour, bark flour, saw flour, and tobacco stem powder. Plant powders such as flour, walnut shell powder, bran, cellulose powder, and residue after extracting plant extracts; Textile products such as paper, dino balls, and furusare; synthetic polymers such as crushed synthetic resins; clays (e.g. kaolin); , bentonite, acid clay), talcs (e.g. talc, pyrophyllite),
Silicas (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic highly dispersed silicic acid, also known as hydrated fine powder silicon or hydrated silicic acid, and some products contain calcium silicate as a main component]), activated carbon, sulfur powder, Examples include inorganic mineral powders such as pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, and calcium phosphate; chemical fertilizers such as ammonium sulfate, ammonium phosphorous, ammonium nitrate, urea, and ammonium chloride; compost; and the like.

These may be used alone or in the form of a mixture of two or more. Materials that can serve as liquid carriers are selected from those that themselves have solvent ability, as well as those that have solvent ability but can disperse the active ingredient compound with the help of adjuvants, such as the following: , these may be used alone or in the form of a mixture of two or more; water, alcohols (e.g. methanol, ethanol, impropatol, methanol, ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl butyl ketone, diyne butyl ketone, cyclohexanone)
, ethers (e.g. ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran)
, aliphatic hydrocarbons (e.g. Ganlin, mineral oil), aromatic hydrocarbons (e.g. benzene, toluene, xylene, rubent naphtha, alkylnaphthalene), halogenated hydrocarbons (e.g. dichloroethane, chlorinated benzene, chloroform, carbon tetrachloride) ), esters (e.g. ethyl acetate, dibutyl phthalate, diimpropyl 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 can be used for convenience 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, alkylaryl ether, polyoxyethylene, alkyl ether, polyoxyethylene, higher fatty acid ester, polyoxyethylene,
Active ingredients such as wmm ester, polyoxyethylene, nrubitan monolaurate, polyoxyethylene, nrubitan monooleate, alkylaryl, sulfonate, natutalenosulfonic acid condensate, lignin sulfonate, higher alcohol sulfate ester, etc. For the purpose of dispersion stabilization, adhesion and binding of compounds, the following may be used, for example: casein, gelatin, starch, alginic acid, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil. , strained oil, bentonite, lignin sulfonate, etc.

For the purpose of improving the flowability of solid products, the following may be used: waxes, stearates, phosphoric acid alkyl esters, etc.

The following may be used as peptizers for suspendable products: naphthalene sulfonic acid condensates, condensed phosphates, etc.

It is also possible to add an antifoaming agent 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 α1 to 50% when used as an emulsion or wettable powder.
(weight) is appropriate.

The herbicide of the present invention can be used as it is or in the form of an appropriate dilution or suspension with water etc. to kill or suppress the growth of various weeds and to protect useful plants from weed damage. An amount effective for suppressing the growth of the weed is applied to the foliage or soil when the outbreak or growth of the weed is unfavorable.

The amount of the herbicide of the present invention to be used depends on various factors, such as purpose, target weeds, weed size or crop outbreak/growth status, weed outbreak tendency, weather, environmental conditions, dosage form, application method, application location, and application. It varies depending on the time of year, etc.

When the herbicide of the present invention is used alone as a selective herbicide,
For example, the dosage of the compound of the present invention is from 0.1 to 10 ares total.
It is appropriate to choose from a ratio of 500g, but considering that when uninvented herbicides are used in combination with other herbicides, they are often effective at lower doses than when used alone. The dosage of the compound of the present invention can also be selected from a smaller dosage range.

The herbicide of the present invention is particularly valuable as a treatment agent for weeds in field crops during their pre-emergence to growth period, or as an early to mid-stage herbicide in paddy fields. It is also possible to use a mixture with other herbicides 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. ethyl 2,4-dichlorophenoxy acetate), MOPC
For example, ethyl 2-methyl-4-chlorophenoxyacetate,
Sodium 2-methyl-4-chlorophenoxyacetate, 2
-Methyl-4-chlorophenoxyacetate), MCP
B (ethyl 2-methyl-4-chlorophenoxybutyrate),
Diclofop methyl (methyl 2-(4-(2゜4-dichlorophenoxy)phenoxy]propanoate); diphenyl ether herbicides such as he-IP (2,4-dichlorophenyl-4'-nitrophenyl ether), CNP
(2,4,6-dichlorophenyl-4'-nitrophenyl ether), chlormethoxynil (2,4-dichlorophenyl-3'-methoxy-4'-nitrophenyl ether), acifluorfen (5 -(2-chloro-α
, α, α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid and its salts), fluazifop-butyl ((±)-2[4-[5-()lifluoromethyl)-2-pyridyl] (oxy]phenoxy]propionic acid butyl ester); triazine herbicides such as CA
T[2-chloro-4,6-bis(ethylamino)-S-
triazine], promethrin [2-methylthio-4,6
-bis(impropylamino)-5-triazine], cymetrine [2-methylthio-4,6-bis(ethylamino)-3-)riazine], metribuzin (4-amino-
6-butyl-3-methylthio-1,2,4-triazin-5 (41()-one); Examples of carbamate herbicides, t ii: Molinate (S-ethylhexahydro-1
H-azepine-1-carbothioate), MCC (methyl N-(6,4-dichlorophenyl)-carbamate)
, IPC [isopropyl N-(3-chlorophenyl)carbamate], benticaope (s-(4-chlorobenzyl)dimethylthiocarbamate); toluidine herbicides such as trifluralin (α,α,α-trifluoro-2,6-sinitro N,N-dipropyl-p-toluidi/), bentimethalin (N-(1-ethylpropyl)
-2,6-sinitro-6,4-xylidine); acid amide herbicides such as DCPA (3,4-dichloropropionanilide), butachlor [2-chloro-2/,6
1-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 (2-10 Rho 2,
6-dinithyru-(2-propoxyethyl)acetanilide; other herbicides such as DCMU (3-(5,
4-dichlorophenyl) 1.1-dimethylurea)
, pentacine (3-isopropyl-(IH)-2゜1.
6-benzothiadiazin-4(3H)-one 2,2-dioxide, virazolate (4-(2°4-dichlorobenzoyl)-1,5-dimethylhyrasol-5-yl-p-toluenesulfonate, Biradixifene (1,
6-dimethyl-4(2,4-dichlorobenzoyl)-5
-Phenacyloxypyrazole, MY-71(4-(
2゜4-dichloro-3-methylbenzoyl) -1゜5
-Dimethylpyrazol-5-yl-p-)luenosulfonate and the like can be mentioned in an embodiment in which the herbicide is used in combination with one or more herbicides.

Some test examples and prescription examples are shown below, but the present invention is not limited thereto.

Test Example 1: Effect on paddy field weeds before budding 1/10,000 Fill soil in a pot and make it into a paddy field.
The tubers of Urikawa were adjusted so that they were in the pre-emergent state.

This was treated with active ingredients (compounds listed in Table 1) as a spray solution at a predetermined concentration. 21 days after treatment, the herbicidal effects were compared with those without treatment, and the herbicidal effects were evaluated using the following criteria.

Criteria for determining herbicidal activity 5...100% weed killing 4...90% or more and less than 100% weed killing 6...80% or more and less than 90% weed killing 2...70% or more and less than 80% weed killing 1...Less than 70% weed killing The results are shown in Table 2.

In the second table, Compound 7 (1-(2,4-dikuoo-
5-((1-ethoxycarbonyl)ethoxy)phenyl)-4-difluoromethyl-3-methyl-Δ'-1,2
, 4-triazolin-5-one) and compound B as compound 14 (1-(2-chloro-4-fluoro)phenyl-4-(j.

1.2.2-f) 7fluoroethyl)-3-methyl-Δ”-1,2,4-)riazolin-5-one).

tried.

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, on the day before the chemical treatment, 2.5-leaf stage paddy rice seedlings (variety Nihonbare) were transplanted and treated with the chemical.

21 days after the treatment, the herbicidal effect and the degree of phytotoxicity on paddy rice were investigated in comparison with the untreated condition.

Tested weed species and their leaf stages: Nobie, 1-leaf stage Konagi, 2-6 leaf stage Chiron cyperus, 1-2 leaf stage Hotarui, 2-3 leaf stage Urikawa, 3-leaf stage Mizugaya cypress Judgment criteria for chemical damage in 1-2 leaf stage H... ... Dog (including withering) M ... Medium L ... Small N ... Criteria for determining herbicidal activity are in accordance with Test Example 1. The results are shown in Table 3.

Table 6 Test Example 6: Effect on field weeds before emergence 10cWLx
Soil was packed in a polyethylene vat of 20 cm x depth scm, and field weeds such as oat, Japanese wild grass, Japanese grasshopper, blueberry, mugwort, Japanese staghorn, Japanese staghorn, and Japanese fir were sown and covered with soil.

The active ingredient was sprayed at a predetermined concentration and then treated, and 21 days after the treatment, the herbicidal effects were investigated in comparison with the untreated treatment.

The criteria for determining herbicidal activity are based on Test Example 1. The results are shown in Table 4.

Table 4 Test Example 4: Effect on field weeds after emergence 10 cfn
The noxious weeds and dice seeds shown below were sown in a polyethylene vat measuring 20 m x 5 crIL in depth, covered with soil, grown until the leaf stage shown below, and treated with a chemical so that the active ingredient was administered at the prescribed dose. .

21 days after the treatment, the herbicidal effect and the degree of phytotoxicity on dice were investigated in comparison with the untreated condition.

Test weed species and their leaf stages and soybean leaf stage oats
Two-leaf grasshopper Two-leaf Aobiyu One-leaf Artemisia One-leaf Kishigisu Two-leaf Cyperus One-leaf Japanese fir One-leaf Dice The criteria for herbicidal activity and herbicidal damage at the first defoliation stage are Test Example 1, respectively.
and 2. The results are shown in Table 5.

Table 5 Prescription Example 1 Irrigation agent made by uniformly mixing and pulverizing 50 parts of Compound 48.

Formulation example 2 Compound layer 30 5 parts bentonite
Granules made by uniformly mixing and pulverizing 90 parts of a clay mixture and 5 parts of calcium kuninsulfonate, adding an appropriate amount of water, kneading well, and granulating.

Prescription example 3

Claims (3)

[Claims] (1) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, R is an alkyl group substituted with a halogen atom; a cycloalkyl group; a cyanoalkyl group; an alkenyl group; an alkynyl group) Group; lower alkoxyalkyl group; lower alkylthioalkyl group; lower alkylsulfinyl alkyl group; lower alkylsulfonylalkyl group; hydroxycarbonyl alkyl group; lower alkoxycarbonyl alkyl group; benzyl group; benzyl group substituted with a halogen atom or a lower alkyl group ; represents a phenethyl group, R^1 represents a haloethyl group, and X represents a halogen atom) Δ^2-1,2,4-triazoline-5-
on derivatives. (2) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R^1 represents a haloethyl group, and X represents a halogen atom.) Compounds and general formulas (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (However, in the formula, R is an alkyl group substituted with a halogen atom; a cycloalkyl group; a cyanoalkyl group; an alkenyl group; an alkynyl group; a lower alkoxyalkyl group) group; lower alkylthioalkyl group; lower alkylsulfinyl alkyl group; lower alkylsulfonylalkyl group; hydroxycarbonyl alkyl group; lower alkoxycarbonyl alkyl group; benzyl group; benzyl group substituted with a halogen atom or lower alkyl group; , Z represents a halogen atom.) General formula (I) characterized by reacting with a compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) and X are the same as above.) A method for producing a Δ^2-1,2,4-triazolin-5-one derivative. (3) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, R is an alkyl group substituted with a halogen atom; a cycloalkyl group; a cyanoalkyl group; an alkenyl group; an alkynyl group) Group; lower alkoxyalkyl group; lower alkylthioalkyl group; lower alkylsulfinyl alkyl group; lower alkylsulfonylalkyl group; hydroxycarbonyl alkyl group; lower alkoxycarbonyl alkyl group; benzyl group; benzyl group substituted with a halogen atom or a lower alkyl group ; represents a phenethyl group, R^1 represents a haloethyl group, and X represents a halogen atom) Δ^2-1,2,4-triazoline-5-
A herbicide characterized by containing an on derivative as an active ingredient.