JPS6327483A - Triazoline compound and production and use thereof - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X is halogen; R1 is 2-5C haloalkyl; R2 is 1-5C alkyl, 3-6C cycloalkyl, phenyl or benzyl; R3 is H, alkali metal, quaternary ammonium salt, 1-6C alkyl, 3-6C cycloalkyl, 3-5C alkenyl, 3-6C alkoxyalkoxyalkyl, etc.). EXAMPLE:3-Chloropropyl alpha-{2,4-dichloro-5-[4-(1,1,2,2-tetrafluoromethyl)-DELTA<2>-1,2,4- triazolin-5-on-1-yl]phenoxy}-alpha-methylthioacetate. USE:A herbicide. PREPARATION:A compound of formula II is reacted with a compound of formula III (Y is halogen) in an inert solvent such as benzene at 0-130 deg.C for 0.5-48hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (I):
5 represents a haloalkyl group, melon represents an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group or a hahenzyl group, and a bird represents a hydrogen atom, an alkali metal atom, or a quaternary ammonium atom. salt, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 3 to 5 carbon atoms, and alkenyl group having 3 to 5 carbon atoms. Substituted by an alkynyl group, an alkoxyalkyl group having a total number of carbon atoms of 2 to 6, an alkoxyalkoxyalkyl group having a total number of carbon atoms of 3 to 6, an alkylthioalkyl group having a total number of carbon atoms of 2 to 7, or a cyano group cyanoalkyl group having 1 to 3 carbon atoms, alkenyloxyalkyl group having 4 to 6 carbon atoms in total, alkoxycarbonylalkyl group having 3 to 6 carbon atoms in total, and 1 to 3 and) represents a phenylalkyl group which may be substituted with a rogen atom or a lower alkoxy group having 1 to 3 carbon atoms, and a phenoxyalkyl group in which the alkyl moiety has 1 to 3 carbon atoms. The present invention relates to the represented 1,2,4-triazolin-5-one derivative, its production method, and herbicide.

The present inventors have discovered that the compound represented by the above general formula (I) is a compound useful as an agricultural drug, especially a herbicide.

The compound of the present invention is a new compound that has not been described in any 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 general formula (I) of the present invention include the methods shown below.

(In the formula, R1, Rt, f%, X and Y are the same as above.) That is, the compound represented by the general formula (I) is a compound represented by the general formula compound in the presence of an inert solvent].

The inert solvent used in this reaction may be one that does not significantly inhibit the progress of this type of reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, etc.
Aliphatic hydrocarbons such as n-hexane and cyclohexane,
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.

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, Trimethylamine, triethylamine, diethylaniline, 1,8-diazabicyclo-(
Organic bases such as 5+'yO)-'-undecene can be mentioned.

The reaction of the present invention can be allowed to proceed at an appropriately determined temperature, for example from 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 α5 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 general formula (I) can also be produced by the method shown below.

(I-b) (where x, horse, melon, and bird are the same as above, and Z is...
Indicates a rogen atom. However, this excludes the case where FLM is a hydrogen atom. ) That is, the compound represented by general formula (I-a) is
It can also be produced by reacting the compound represented by the general formula (I-b) with an alcohol or a ride corresponding to RsK and esterifying it.

Representative examples of the compound represented by the general formula (T) are shown below.
Shown in the table.

General Formula (I): The NMR spectrum data of Compound A1 in Table 1 is shown below.

Shi4 (S, IH), &8 (tt, 1m-1).

7.1 (S, 1) 1), 7.55-11.0 (S.

IH) The compound represented by the general formula (l[D is
It can be produced by the method described in Japanese Patent No. 1069.

Examples of non-invention are shown below, but the present invention is not limited thereto.

Example 15-Chloropropyl α-(2,4-dichloro-
5-(4-(1,1,2,2-tetrafluoromethyl-
Δ'-1.2.4-triazolin-5-one-1-yl)phenoxif-α-methylthioacetate (compound 3) Potassium carbonate α52 (cL0037 mol)'j(
Mflj in 50-molar N,N-dimethylformamide,
Add 1-(2,4-dichloro-4-hydroxyphenyl)-3-methyl-'-('+'+2+2-
After adding 36 g (10,034 moles) of 1,2,4-triazolin-5-one (tetrafluoroethyl)-Δ"-1, and stirring at room temperature for 30 minutes, 3-chloropropyl α-bromo-α-methylthioacetyl) cL89? ((LO
34 moles of O2) was added thereto, and the reaction was carried out at 50'C for 3 hours. After the reaction was completed, the reaction solution was poured into ice water at room temperature, 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.
5-(4-(1,1,2,2-tetrafluoroethyl)
-3-Methyl-Δ-1.2.4-triazolin-5-on-1-yl]phenoxy)-α-methylthioacetate (compound 77) 544t (IllL01 mol) of 1-(4-chloro-2
-fluoro-5-hydroxyphenyl)-4-(1,1
,2,2-tetrafluoroethyl)-5-methyl-Δ”
-1,2,4-triazolin-5-one, L84P(a
o 11 mol) (Dif lumi -) o mo a-
50 methylthioacetate and 5,449 potassium carbonate
The mixture was added to ml of acetone and heated under reflux for 3 hours.

After the reaction is completed, the reaction solution is allowed to cool to room temperature, and the insoluble materials are removed.
Acetone is distilled off under reduced pressure to obtain a soybean oil. The resulting oily substance was purified by column chromatography for purpose 1.
I got a score of 4.91.

n, ol, 5149 Yield 9a9% Example 5
4-chlorobenzyl α-(2-ri0low5-(4-(2
-Chloro-1,1,2-trifluoroethyl)-s-methyl-Δ-1121'-triazolin-5-one-1-
yl]-a-fluorophenoxy)-α-methylthioacetate (compound 11; x 141 ) 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-(2-chloro-1, 1,2-trifluoroethyl)-Δ″-1゜2.4-triazolin-5-one 2
．． 05P (α0051 mol), potassium carbonate 1.5 and 4-chlorobenzyl α-bromo-α-methylthioacetate 1,751 (00056 mol) were added to 50 ml of methyl ethyl ketone and heated under reflux for 5 hours. After the reaction solution was cooled to room temperature, the insoluble matter was separated by V, the P solution was condensed to zero, and the residue was purified by dry column chromatography to obtain the desired product.

fn, 9.95°C Yield 78% Example 4 Sodium α-(4-chloro-5-(a-(1,1,2,2
-tetrafluoroethyl)-3-methyl-Δ”-1,2
,4-triazolin-5-one-1-yl]2-fluorophenoxy)-α-difluoromethylthioacetate (compound &76) (a-(4-rioo-5) of L45f (n001 mol)
-(a-(1,1,2,2-tetrafluoroethyl)
-5-methyl-Δ”-1,2,4-triazoline-5-
O/-1-yl2-fluorophenoxy)-α-methylthioacetic acid was added to a methanol solution containing 145f (α001 mol) of NaOH and stirred for 30 minutes. After the reaction is completed, methanol is distilled off, and the obtained crystals are washed with ether and dried to obtain the target product cLast.

m, p, 14S1°C Yield 92.1% Example 5
3-bromopropyl α-(2,4-dichloro-5-(
a-(2-chloro-1,1゜2-trifluoroethyl)
-3-methyl-Δ”-1,2,4-triazoline-5-
on-1-yl]phenoxy)-α-isofurohylthioacetate (compound &59) t 0 3-bromopropatol 1431 (α0031 mol) f
50 mL of tetrahydrofuran, dicyclocarbodiimide 145 @ (α0022 mol) and dimethylaminopyridine 0.02 f were added to this solution, and α-(2,4-dichloro-5- [(2-chloro-1,1,2-trifluoroethyl)-3-methyl-Δ-1,2,4-triazolin-5-one-1-yl]phenoxy)-α-isopropylthioacetic acid t02(α
002 mol) and stirred at room temperature for 2 hours. After the reaction is complete, insoluble materials are removed by FF, the solvent is distilled off under reduced pressure, and the resulting oil is purified by column chromatography to obtain the desired product. Obtained.

n22 t5316 yield 1.5516 fruits 21
[1i Example 6 1-(ethoxycarbonyl)ethyl α-(
2-chloro-4-fluoro-5-(4-(2-chloro-
1,1,2-)lifluoroethyl)-3-methyl-Δ”
-1,2,4-triazolin-5-one-1-yl]phenoxy)-α-7enylthioacetate (compound &1
64) α-(2-chloro-4-fluoro-5-[4-(2-chloro-1,1,2-)lifluoroethyl)-3-methyl-Δ-1.2.4-triazoline-5- on-1-yl]phenoxy)-α-phenykf oacetic acid α74f (α0
0143 mol), ethyl α-bromopropionate α3
Potassium carbonate of 7f ((LOO2 mol) and (L28f) was added to s o mt of acetone and heated under reflux for 5 hours. 6. After the reaction was completed, the solution was allowed to cool to room temperature, the insoluble matter was removed, and the solvent was removed. The residue was distilled off to obtain an oily substance.The obtained oily substance was purified by column chromatography to obtain the target product lyf.

n'' t5577 Yield 79.5 The '+2+'-)'J azolin-5-one derivative of the present invention represented by the general formula (I) is, for example, Noeko (common name for Japanese millet).

1-year-old oxcart of the Poaceae family, a typical harmful grass of paddy fields), and Japanese grass (1-year-old oxcart of the Poaceae family).

(Harmful grass in paddy fields), Cyperus japonica (Cyperaceae, one-year-old oxcart, paddy field government army), Cyperaceae (Cyperaceae, perennial oxcart. Occurs in wetlands, waterways, and paddy fields).

Typical perennial weeds of paddy fields), Urikawa (Omodaceae. A perennial pest that occurs in rice fields, wetlands, and ditches) (Cyperaceae perennial, occurring in oxcarts, paddy fields, wetlands, and inns) '4 Annual and perennial weeds in paddy fields, Oat (Poaceae biannual ox cart.

Occurs on flatlands, wastelands, and fields), Mugwort (perennial oxcart of the Asteraceae family).

Occurs in mountains, fields, and fields), Poaceae (Poaceae, 1 year old oxcart, fields,
Typical harmful grasses in orchards), Gishigishi (Polygonaceae perennial oxcart,
Occurs in fields and roadsides), Cyperaceae (Cyperaceae 1st year ox carts, 1st year ox carts, fields and roadsides), Bluetail (1st year engineering ox carts. Occurs in vacant lots, roadsides and fields), Asteraceae 1 year ox carts. Strength of soybean It has the effect of controlling annual and perennial weeds that occur in fields and orchards, such as harmful plants.

The triazolin-5-one derivative represented by the above general formula (I) exhibits outstanding herbicidal activity against weeds in the pre-emergent and growing stages. ) The compound of the present invention is useful as a herbicide for pre-soil treatment, post-sowing soil treatment, soil treatment during crop growth, foliage treatment before sowing (planting) of crops, and foliage treatment during crop growth. It is useful as an early and mid-term herbicide, and also as a herbicide for general weeds, such as mowing marks, fallow fields, ridges, farm roads, waterways, pasture land, cemeteries, parks, roads, playgrounds, open spaces around buildings, and cultivated land. It can also be used to exterminate common weeds in areas such as railways, 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 an agrochemical formulation in a form suitable for use according to a conventional method.

That is, the above compound is prepared by blending it in a suitable inert carrier in an appropriate proportion together with an auxiliary agent if necessary.
They may be dissolved, separated, suspended, mixed, impregnated, adsorbed, or adhered to form 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 serve as solid carriers include soybean flour, grain flour, wood flour, bark flour, sawdust, Vegetable powders such as tobacco stem powder, walnut flour, bran, cellulose powder, and residue after extracting plant extracts; Textile products such as gi, cardboard, and furusare; Synthetic polymers such as crushed synthetic resins; Clays (e.g. kaolin, bentonite, acid clay), Merck (e.g. talc, hylophyllite),
Silicas (for example, diatomaceous earth, borax, mica, white carbon [synthetic highly dispersed sulfuric acid, also known as hydrated fine powder silicon or hydrated silicic acid, and some products contain calcium silicate as a main component]), activated carbon, Inorganic mineral powders such as sulfur powder, pumice, Seisei diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, calcium phosphate; chemical fertilizers such as ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc., compost, etc. can be mentioned.

These can be used alone or in the form of a mixture of two or more types. Materials that can serve as liquid carriers are selected from those that themselves have solvent capacity, as well as those that allow the active ingredient to be dispersed with the help of adjuvants even if they have one solvent capacity, such as the following: These are used alone or in a mixture of two or more; water,
Alcohols (e.g. methanol, ethanol, isopropanol, butanol, ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diimbutyl ketone, cyclohexanone), ethers (e.g. ethyl ether, dioxane, cellosolve, dioxane), propyl 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 alkylaryl ether, polyoxyethylene alkyl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene
Dispersion stabilization of active ingredient compounds such as resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfone an, naphthalene sulfonic acid condensates, lignin sulfonates, higher alcohol sulfate esters, For adhesion or bonding purposes, the following may be used, for example: casein, gelatin, starch, alginic acid, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil, hemp, hentonite, lignin sulfone. For the purpose of improving the flowability of solid products such as acid salts, the following may be used: waxes, etc., stearic acid salts, 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 oils.

The combination of active ingredients can be adjusted as necessary.

When used as a powder or granule, it is usually 15 to 20 inches (by weight)
When used as an emulsion or an aquarium, a suitable amount is 1 to 50 inches (by weight).

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. Effective 1 is used by applying it to the foliage or soil on the weed or in a place where the emergence or growth of the weed is unfavorable.

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

When the herbicide of the present invention is used alone as a selective herbicide,
For example, if the compound of the present invention is withdrawn fr, 10 ar/α1
It is appropriate to select the herbicide from a ratio of 5,000 to 5,001, but it should be taken into consideration that when the herbicide of the present invention is used in combination with other herbicides, it is often effective at a lower dose than when used alone. For example, the dosage of the compound of the present invention can be selected from a smaller dosage range.

The herbicide of the present invention has high value as a treatment agent from before the emergence of weeds in field crops to the growth period, or as an early to mid-stage herbicide in paddy fields, but it is also useful as a herbicide for expanding the target grass species and the suitable period for control, or as a treatment agent for the growth period of weeds in field crops. It is also possible to mix with other herbicides to reduce the amount and is within the scope of the present invention. for example,
Phenoxy fatty acid herbicides such as 2.4-PA (e.g. ethyl 2.4-dichlorophenoxyacetate), MCP (e.g. [z-methyl-4-chlorophenoquine ethyl acetate,
-Methyl-4-chlorophenoxy vinegar□□□Sodium,
allyl 2-methyl-4-chlorophenoxyacetate), MC
PB (2-methyl-4-chlorophenoxyethyl phosphate)
, diclofopmethyl (methyl 2- (4-(2,4-
dichlorophenoxy)phenoxy]furopanoate);
Diphenyl ether herbicides such as NIP (2m'-"
Chlorphenyl-4-nitrophenyl ether), CN
P(2,A,6-dichlorophenyl-4-nitrophenyl ether), chlormethoxynil (2,a-dichlorophenyl-3-meth)*cy-4-nitrophenyl ether), acifluorfen (5-(2- / Roro α, α.

α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid and its salts), fluazifop-butyl ((±)-2(4-((5-()Ufluoromethyl)-2-pyridyl)okyne [phenoxy]zolopion modified butyl ester); triazine herbicides such as CAT (
2-chloro-4,6-bis(ethylamino)-s-)riazine], chromethrine [2-methylthio-4゜6-bis(inpropylamine)-S-triazine], cymetrine [2-methylthio-4, 6-bis(ethylamino)
-S-triazine], metribuzin (4-amino-6-
1-butyl-3-methylthio-1,2,4-triazin-5(4)1)-one); carbamate herbicides such as moline) (S-ethylhexahydro-1H-azepine-1-carbothioate ), MCC(methyl N”(3+
'-dichlorophenyl)-carbamate], IPC(,
l sozolopyl N-(3-chlorphenyl)carbamate], penticaope (s-(4-chlorobenzyl) dimethylthiocarbamate); toluidine herbicides such as trifluralin (α,α,α-trifluoro2.6
-Sinitro N, N-dipropyl-p-toluidine),
Pendimethalin (N-(1-ethylpropyl)-2,
Acid amide herbicides such as L) CPA (3,a-dichloropropionani IJ)'), butachlor [2-chloro-2'16'-
diethyl-he-(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-
dinityl-N-(2-propoxyethyl)acetanilide; other herbicides such as DCMU (S-(3,a-
(dichlorophenyl)-1,1-dimethylurea), pentacine (3-impropyl-(I H)-2*1.3
-benzothiadiazin-4(5)()-one 2,2-dioxide, virazolate (4-(2*4-9chlorobenzoyl)-1,5-cy)fA'hyrasol-5-
yl-1)-)luninsulfonate, biradixifene (1,3-dimethyl-4(z,4-dichlorobenzoyl)-5-7enacruoxypyrazole, MY-71(4
-(2゜4-dichloro-3-methylbenzoyl)"'s
An embodiment can be mentioned in which the herbicide is used in combination with one or more herbicides such as 3-dimethylpyrazol-5-yl-p-)luene sulfonate.

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

Test Example 1: Effect on pre-emergent paddy field weeds Fill a 1/10,000th R pot with soil to make it into a paddy field, and prepare the paddy field weeds such as field weeds, Japanese grasshopper, Japanese cypress, firefly seeds, and urikawa tubers before they emerge. Adjusted to.

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 of each treatment were compared with those without treatment, and judgments were made based on the following criteria.

Judgment criteria for herbicidal activity 5 - 100% weed killing 4... 90% or more 1t) Less than 0% weeding 3... 80 or more but less than 90 weeding 2... 70% or more and less than 80% weeding 1 ...Less than 70% weed killing result'f: Shown in Table 2.

In Table 2, Control A and Control B are the compounds &7.1-(2,4-dichloro-5-(1
-(ethoxycarbonyl)ethoxy]2-enyl)-4-
difluoromethyl-3-methyl-Δ2-1.2.4-triazolin-5-one, and the compound &14.1-(4-
Chloro2-fluorophenyl)-3-methyl-4-(1
, 1,2,2-tetrafluoroethyl)-Δ2-1.2
．． 4-triazolin-5-one was used.

Test Example 2: Effect on paddy field weeds after germination A 1/10,000 R pot was filled with soil 1, and the paddy field conditions were maintained to grow harmful weeds at the following leaf stages.The day before chemical treatment, paddy rice at the 2.5 leaf stage was grown. Seedlings (variety: Nipponbare) were t-transplanted and treated with drugs. 21 days after the treatment, the herbicidal effect and the degree of phytotoxicity on paddy rice were investigated in comparison with the untreated treatment.

Test weed species and their leaf stages: No. 1 Leaf stage
Ki 2nd to 6th leaf stage
1st to 2nd leaf stage Firefly 2nd to 3rd leaf stage Prunus vulgaris 3rd leaf stage Mizugaya sypera Judgment criteria for chemical damage in 1st to 2nd leaf stage H...Large (including withering) M...Medium L... ...Small N...The criteria for determining herbicidal activity are in accordance with Test Example 1. The results are shown in Table 3.

Table 3 Test Example 3: Effect on field weeds before emergence 10cWIX
20cWIX depth 55! A polyethylene vat was filled with soil, and upland weeds such as oats, Japanese wild grass, Japanese grasshopper, blueberry, mugwort, Japanese grass, Japanese staghorn, and Japanese fir were sown and covered with soil.

The active ingredients were sprayed at a predetermined concentration and treated, and 21 days after the treatment, the herbicidal effects of each were investigated compared to the untreated one.

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 I on field weeds after emergence I QcWI
X 20 t-nt processed.

21 days after the treatment, the herbicidal effect and the degree of chemical damage to soybean were investigated in comparison with the untreated condition.

Test weed species and their leaf stages and soybean leaf stage oats
2-leaf stage Aobiyu 2-leaf stage Aobiyu 1-leaf stage Mugwort 1 leaf stage Gishigishi 2
Leaf stage Kogomega cypress 1 Leaf stage Onamomi 1
Leaf stage soybean 1st compound leaf stage The criteria for herbicidal activity and the criteria for chemical damage are Test Example 1, respectively.
and 2. The results are shown in Table 5.

Table 5 Prescription example 1 Compound IE, 150 parts A hydrating agent made by mixing and pulverizing the metal.

Formulation example 2 Compound product 75 parts Bentonite clay mixture 90 parts Calcium ligninsulfonate 5
Mix and grind the parts uniformly and add an appropriate amount of water. In addition, granules are made by thoroughly kneading and granulating.

Formulation Example 3 Compound J31 50 parts Xylene 40 parts Mixture with calcium nitrate 10 parts Emulsion prepared by uniformly mixing the whole compound.

Claims (6)

[Claims] (1) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X represents a halogen atom, R_1 represents a haloalkyl group having 2 to 5 carbon atoms, and R_2 represents a carbon Number of atoms: 1
-5 alkyl group, cycloalkyl group having 3 to 6 carbon atoms, phenyl group, or benzyl group, R_3 is a hydrogen atom, an alkali metal atom, a quaternary ammonium salt, an alkyl group having 1 to 6 carbon atoms, a carbon Haloalkyl group having 1 to 5 atoms, cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 3 to 5 carbon atoms, alkynyl group having 3 to 5 carbon atoms, and having a total number of carbon atoms of 2 to 6 an alkoxyalkyl group, an alkoxyalkoxyalkyl group having a total of 3 to 6 carbon atoms, an alkylthioalkyl group having a total of 2 to 7 carbon atoms, a cyanoalkyl group having 1 to 3 carbon atoms substituted with a cyano group, An alkenyloxyalkyl group having a total number of carbon atoms of 4 to 6, an alkoxycarbonylalkyl group having a total number of carbon atoms of 3 to 6, an alkyl moiety having 1 to 3 carbon atoms, and a halogen atom or a carbon atom number of 1 to 6. 3, a phenylalkyl group optionally substituted with a lower alkoxy group,
and a phenoxyalkyl group in which the alkyl moiety has 1 to 3 carbon atoms. ) A 1,2,4-triazolin-5-one derivative represented by: (2) The 1,2,4-triazolin-5-one derivative according to claim 1, wherein X is a fluorine atom. (3) General formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (In the formula, X represents a halogen atom, and R_1 represents a haloalkyl group having 2 to 5 carbon atoms.) Compounds and general formula (II): ▲Mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, Y represents a halogen atom, R_3 represents a hydrogen atom,
Alkali metal atom, quaternary ammonium salt, number of carbon atoms: 1
-6 alkyl group, C1-5 haloalkyl group, C3-6 cycloalkyl group, C3-C3 alkyl group
~5 alkenyl groups, alkynyl groups having 5 to 5 carbon atoms, alkoxyalkyl groups having a total number of carbon atoms of 2 to 6, alkoxyalkoxyalkyl groups having a total number of carbon atoms of 3 to 6, total number of carbon atoms an alkylthioalkyl group having 2 to 7 carbon atoms, a cyanoalkyl group having 1 to 3 carbon atoms substituted by a cyano group, an alkenyloxyalkyl group having a total number of carbon atoms of 4 to 6, and a total number of carbon atoms having 3 to 6 an alkoxycarbonylalkyl group, an alkyl moiety having 1 to 3 carbon atoms and a phenylalkyl group which may be substituted with a halogen atom or a lower alkoxy group having 1 to 3 carbon atoms, and an alkyl moiety having 1 to 3 carbon atoms; 3 shows the phenoxyalkyl group. ) General formula (I) characterized by reacting a compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X, R_1, R_2 and R_3 are the same as above.) A method for producing the 1,2,4-triazolin-5-one derivative shown below. (4) The method for producing a 1,2,4-triazolin-5-one derivative according to claim 3, wherein X is a fluorine atom. (5) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X represents a halogen atom, R_1 represents a haloalkyl group having 2 to 5 carbon atoms, and R_2 represents a
-5 alkyl group, cycloalkyl group having 3 to 6 carbon atoms, phenyl group, or benzyl group, R_3 is a hydrogen atom, an alkali metal atom, a quaternary ammonium salt, an alkyl group having 1 to 6 carbon atoms, a carbon Haloalkyl group having 1 to 5 atoms, cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 3 to 5 carbon atoms, alkynyl group having 3 to 5 carbon atoms, and having a total number of carbon atoms of 2 to 6 an alkoxyalkyl group, an alkoxyalkoxyalkyl group having a total of 3 to 6 carbon atoms, an alkylthioalkyl group having a total of 2 to 7 carbon atoms, a cyanoalkyl group having 1 to 3 carbon atoms substituted with a cyano group, An alkenyloxyalkyl group having a total number of carbon atoms of 4 to 6, an alkoxycarbonylalkyl group having a total number of carbon atoms of 3 to 6, an alkyl moiety having 1 to 3 carbon atoms, and a halogen atom or a carbon atom number of 1 to 6. 5, a phenylalkyl group optionally substituted with a lower alkoxy group,
and a phenoxyalkyl group in which the alkyl moiety has 1 to 3 carbon atoms. ) A herbicide characterized by containing a 1,2,4-triazolin-5-one derivative represented by the following as an active ingredient. (6) The herbicide according to claim 5, wherein X is a fluorine atom.