JPH0321522B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula (): (wherein, X represents a halogen atom, R ¹ represents an alkyl group having 1 to 4 carbon atoms, Y represents a hydrogen atom, an alkyloxy group having 1 to 4 carbon atoms,
Alkenyloxy group having 2 to 4 carbon atoms, alkynyloxy group having 3 to 4 carbon atoms, halomethyloxy group, haloethyloxy group, alkyloxycarbonylalkyl group in which the total number of carbon atoms in the alkyl group is 3 to 6. Represents a phenylalkyloxy group in which the oxy group or alkyl group has 1 to 4 carbon atoms, and R ² is 1 to 4 carbon atoms.
to 4 alkyl group, halomethyl group or haloethyl group. However, in the above definitions ^of Y, R ² and In the case of 2 to 4 alkenyloxy groups,
R ² is a haloethyl group, and X is a chlorine atom,
When Y is an alkynyloxy group having 3 to 4 carbon atoms or a phenylalkyloxy group having 1 to 4 carbon atoms,
R ² represents a halomethyl group, and when Y is a halomethyloxy group or a haloethyloxy group, R ² is an alkyl group having 1 to 4 carbon atoms,
Represents a halomethyl group or a haloethyl group, and when Y is an alkyloxycarbonylalkyloxy group in which the total number of carbon atoms in the alkyl group is 3 to 6, R ² is a halomethyl group and X represents a chlorine atom shall be. ) Δ ² -1,2,4-triazoline-
The present invention relates to a herbicide containing 5-ones as an active ingredient. The compound represented by the above general formula () used as an active ingredient in the present invention is a new compound that has not been described in any literature, and a typical synthesis method thereof is A.
Law and B Law are mentioned. The reaction route is diagrammatically shown as follows. (In the formula, X, Y, R ¹ and R ² are the same as above. When Y is a halomethyloxy group or a haloethyloxy group, R ² excludes a hydrogen atom. Z is a chlorine atom, a bromine atom, and an iodine atom. (R ² Z can also represent haloethylene.) (In the formula, X and R ¹ are the same as above. Y ¹ is an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 3 to 4 carbon atoms, a halomethyl group, a haloethyl group. group, an alkyloxycarbonylalkyl group in which the total number of carbon atoms in the alkyl group is 3 to 6, or an alkyl group in which the total number of carbon atoms is 1 to 4
represents a phenylalkyl group, and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halomethyl group or a haloethyl group. However, in the above definitions of Y ¹ , R ² and X, when Y ¹ is an alkyloxy group having 1 to 4 carbon atoms or an alkenyloxy group having 2 to 4 carbon atoms, R ² is a haloethyl group. In addition, when X represents a chlorine atom, and Y ¹ is an alkynyloxy group having 3 to 4 carbon atoms or a phenylalkyloxy group whose alkyl group has 1 to 4 carbon atoms, R ² is a halomethyl group. , and when Y ¹ is a halomethyloxy group or a haloethyloxy group, R ² is a hydrogen atom and has 1 carbon atom.
to 4 alkyl group, halomethyl group, or haloethyl group, and when Y ¹ is an alkyloxycarbonylalkyloxy group in which the total number of carbon atoms in the alkyl group is 3 to 6, R ² is a halomethyl group or haloethyl group. group, and X represents a chlorine atom. ) In other words, in Method A, the compound represented by the general formula () and the compound represented by the general formula () are combined, and in Method B, the compound represented by the general formula () and the compound represented by the general formula It can be obtained by reacting the compound represented by () in an inert solvent in the presence of a base. The inert solvent used in these reactions 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, for example, inorganic bases such as sodium carbonate, sodium hydride, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydroxide, potassium hydroxide and alcoholates of alkali metals;
Examples include organic bases such as pyridine, trimethylamine, triethylamine, diethylaniline, 1,8-diazabicyclo-[5,4,0]-7-undecene, but especially sodium hydroxide,
Inorganic bases such as potassium hydroxide and potassium carbonate are preferred. When reacting the compound represented by the general formula () with the compound represented by the general formula (), the compound represented by the general formula () can be obtained in good yield by performing the reaction in the presence of a quaternary ammonium salt (however, (Except when R ² Z in formula () represents haloethylene). The reaction of the present invention is generally carried out under heating, e.g.
The process can be carried out at an appropriately determined temperature within the range of ~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. After the reaction is completed, the target product can be collected by treating the reaction product in a conventional manner. Representative examples of compounds represented by the general formula () are as follows.

【table】

[Table] The compound represented by the general formula () can be synthesized by the following reaction route. (In the formula, R ¹ , X and Y are the same as above, 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 formula (2) is reacted in an inert solvent under heating, and the resulting compound represented by formula () is isolated, or without isolation, by ring-closing reaction in the presence of a base. Can be done.

【table】

[Table] Furthermore, the compound represented by the general formula () can be synthesized by the following reaction route. (In the formula, X, R ¹ and R ² N are the same as above. R represents an alkyl group having 1 to 3 carbon atoms.) In this reaction, in place of hydrobromic acid, hydrogen iodide or alkylthio Lato may also be used.

[Table] Synthesis example 1 1-(2-fluoro-4-chlorophenyl)-3
-Methyl-4-difluoromethyl-Δ ² -1,2,
Synthesis of 4-triazolin-5-one (Compound No. 3). 0.8 g (0.0035 mol) of 1-(2-fluoro-4-
Chlorophenyl)-3-methyl-Δ ² -1,2,4
About 2 g of chlorodifluoromethane are passed under reflux into a mixture of -triazolin-5-one, 0.2 g of water, 1 g of tetrabutylammonium bromide, 1 g of caustic soda and 30 ml of cyclohexane over the course of 1 hour. After cooling to room temperature, water and ether are added and the organic layer is collected. After washing this in the order of dilute caustic soda solution, water, dilute hydrochloric acid, and water,
Dry and evaporate the solvent to obtain crystals. Recrystallization from n-hexane yields 0.27 g of the desired product. Melting point 118.6°C, yield 27.8% Synthesis example 2 1-(2,4-dichloro-5-propargyloxyphenyl)-3-methyl-4-difluoromethyl-Δ ² -1,2,4-triazoline-5- Synthesis of On (Compound No. 8). 0.54 g of 1-(2,4-dichloro-5-oxyphenyl)-3-methyl-4-difluoromethyl-
Δ ² -1,2,4-triazolin-5-one, 1g
of potassium carbonate, 0.5 g of propargyl bromide and 30 ml of acetone is refluxed for 2 hours. After cooling, potassium carbonate is removed and acetone is distilled off to obtain crystals. This was recrystallized from n-hexane to obtain 0.59 g of the desired product. Melting point 114.4°C, yield 98.3% Synthesis example 3 1-(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-4-(1,1,2,2-
Synthesis of (compound No. 23) -Δ ² -1,2,4-triazolin-5-one (compound No. 23). Dissolve 3.02 g (0.01 mol) of 1-(2,4-dichloro-5-isopropoxyphenyl)-3-methyl-Δ ² -1,2,4-triazolin-5-one in 60 ml of dimethylformamide, and add water. Add 0.40g (0.01 mol) of sodium oxide powder and heat to 50-60°C. Add 16.25g of zinc to this mixture and 120g of methanol.
1,2-dibromo-1,1,
20g of 2,2-tetrafluoroethane in methanol
After bubbling the tetrafluoroethylene gas obtained by dropping the solution dissolved in 20 ml, the reaction mixture was poured into ice water.
Pour into 200 ml, extract with ether, wash twice with 10% aqueous sodium hydroxide solution, wash with water, wash with saturated saline, and dry over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of ethyl ether and petroleum ether to obtain 1.47 g of the desired product. Melting point 102-103.5℃, yield 36.5% Synthesis example 4 1-[2,4-dichloro-5-(2-chloro-1,
1,2-trifluoroethoxy)phenyl]-3
-Synthesis of methyl-4-methyl-Δ ² -1,2,4-triazolin-5-one (compound No. 19). 1-(2,4-dichloro-5-oxyphenyl)
-3-methyl-4-methyl-Δ ² -1,2,4-
0.69 g (0.0025 mol) of triazolin-5-one is dissolved in 30 ml of dimethylformamide, 0.10 g (0.0025 mol) of sodium hydroxide powder is added, and the mixture is heated to 50-60°C. A solution of 5 g of 2-chloro-1,1,2-trifluoromethane dissolved in 10 ml of methanol is added dropwise to a suspension of 6.0 g of zinc in 60 ml of methanol, and the resulting chlorotrifluoroethylene gas is added to the above mixture. After that, the reaction mixture was poured into 110 ml of ice water, extracted with ether, washed twice with 10% aqueous sodium hydroxide solution, washed with water, washed with saturated brine, and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl ether.
Recrystallize with petroleum ether to obtain 0.93g of the desired product. Melting point 108-111℃, yield 98.0% Synthesis example 5 1-[2,4-dichloro-5-(1,1,2,2
Synthesis of -tetrafluoroethoxy)phenyl]-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ ² -1,2,4-triazolin-5-one (Compound No. 26) . 1-(2,4-dichloro-5-oxyphenyl)
0.78 g (0.003 mol) of -3-methyl-Δ ² -1,2,4-triazolin-5-one is suspended in dimethylformamide, 0.25 g of sodium hydroxide is added, and the mixture is heated to 50-60°C. A solution of 10 g of 1,2-dibromo-1,1,2,2-tetrafluoroethane dissolved in 20 ml of methanol is added dropwise to a suspension of 8.13 g of zinc in 80 ml of methanol, resulting in tetrafluoroethylene gas. was aerated into the above mixture, and then the reaction mixture was poured into 100 ml of ice water.
After extraction with ether, treatment is performed according to a conventional method to obtain 0.33 g of the desired product as an oil. n _D ^{15.0 1.4840} , yield 23.9% Synthesis example 6 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-difluoromethyl-3-methyl-Δ ² -1,2,4 -Synthesis of triazolin-5-one (compound No. 30). 0.51 g of 1-(4-chloro-2-fluoro-5-
oxyphenyl)-4-difluoromethyl-3-
Methyl-Δ ² -1,2,4-triazoline-5-
A mixture of 1 g of potassium carbonate, 0.5 g of propargyl bromide and 330 ml of acetone is heated to reflux for 2 hours. After the reaction is completed, the reaction solution is cooled, potassium carbonate is filtered off, acetone is distilled off from the filtrate, and the resulting residue is purified by dry column chromatography to obtain 5.3 g of the desired product. Melting point 84-85℃ Yield 92.1% Reference synthesis example 1 1-(2-fluoro-4-chlorophenyl)-3
-Methyl-Δ ² -1,2,4-triazoline-5
−Synthesis of on. After heating 5 g (0.031 mol) of 2-fluoro-4-chlorophenylhydrazine and 5 g (0.031 mol) of 1-(ethoxy)ethylidene urethane at 80°C for 30 minutes in 30 ml of xylene, 3.2 g (0.031 mol) of 2-fluoro-4-chlorophenylhydrazine mole)
of triethylamine is added and refluxed for 2 hours. After cooling to room temperature, extract twice with 30 ml of 10% aqueous sodium hydroxide solution, wash the aqueous layer with ether, and acidify with hydrochloric acid to obtain 5.5 g of crystals of the desired product. Melting point: 199.7°C, yield: 76.8% Reference synthesis example 2 1-(2,4-dichloro-5-oxyphenyl)
-3-methyl-4-difluoromethyl-Δ ² -1,
Synthesis of 2,4-triazolin-5-one. 6 g (0.017 mol) of 1-(2,4-dichloro-5-
A mixture of 60 ml of 47% hydrobromic acid and 150 ml of acetic acid is refluxed for ⁴ hours. After cooling, most of the acetic acid is distilled off under reduced pressure, 150 ml of ice water is added, and the mixture is cooled with ice. Collect the resulting crystals to obtain 5.03g of the target product. Melting point: 175.3°C, yield: 95.3% Δ ² −1,
Examples of 2,4-triazolin-5-ones include Novie (common name for Japanese millet), an annual grass of the Poaceae family, a typical harmful grass of paddy fields, and Konagi (an annual grass of the Poaceae family).
A grass that is harmful to rice fields), Cyperus japonica (an annual grass of the family Cyperaceae, a harmful grass of rice fields), Cyperus japonica (a perennial grass of the family Cyperaceae, which occurs in wetlands, waterways, and rice fields. A typical harmful perennial grass of rice paddies), Urikawa (family Cyperaceae). A perennial harmful grass that occurs in paddy fields, wetlands, and ditches), firefly (a perennial grass of the Cyperaceae family that occurs in rice paddies, wetlands, and ditches), oat (a perennial grass of the Poaceae family that occurs on flatlands, wastelands,
(occurs in fields), mugwort (a perennial grass of the Asteraceae family. Yamano,
Occurs in fields), Poaceae (grass annual grass, fields,
Typical harmful grass in orchards), Gishigishi (a perennial grass of the Polygonaceae family. Occurs in fields and roadsides), Cyperus japonica (an annual grass of the Cyperaceae family, occurs in fields and roadsides), Aobiyu (an annual grass of the family Arunaceae family. Occurs in open spaces and roadsides) ,
It has the effect of controlling annual and perennial grasses that occur in paddy fields, fields, orchards, wetlands, etc. Compounds represented by the above general formula () exhibit excellent control effects on weeds before budding and in the early stages of emergence, so they may be applied in advance to the area where useful plants are planned to be planted, or after the planting of useful plants ( The characteristic physiology of the compound of the present invention can be further improved by treating the weeds before they begin to emerge (including when useful plants have already been planted in a garden) or after sowing useful plants and before the emergence of crops. The activity can be effectively expressed. However, the herbicide of the present invention does not have to be used only in this manner; for example, the herbicide of the present invention can not only be used as a mid-term herbicide in paddy fields, but also for weeding common weeds. It can also be used as an agent. For example, it can be used to exterminate general weeds in mowing areas, fallow fields, ridges, farm roads, waterways, pasture land, cemeteries, parks, roads, playgrounds, open spaces around buildings, cleared land, railroad tracks, forests, etc. can. 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 form convenient for use according to conventional methods for agricultural chemical formulations. That is, the above-mentioned compound is blended with an appropriate inert carrier in an appropriate ratio together with an auxiliary agent if necessary, and dissolved, dispersed, suspended, mixed, impregnated, adsorbed, or adhered to an appropriate dosage form. For example, it may be formulated into a suspension, emulsion, solution, wettable powder, powder, granule, tablet, etc. 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, residue after extracting plant extracts; textile products such as paper, cardboard, and shavings; pulverization Synthetic polymers such as synthetic resins; clays (e.g. kaolin, bentonite, acid clay), talcs (e.g. talc, hirophyllant), silicas (e.g. diatomaceous earth, silica sand, mica,
White carbon (synthetic highly dispersed silicic acid, also known as hydrated fine powder silica or hydrated silicic acid; some products contain calcium silicate as a main component)), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks. , fly ash, sand, calcium carbonate, calcium phosphate, and other inorganic mineral powders; chemical fertilizers such as ammonium sulfate, ammonium phosphorus, ammonium nitrate, 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 are selected from those that themselves have solvent ability, as well as those that do not have solvent ability but can disperse the active ingredient compound with the help of an adjuvant, such as the following: However, these can be 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, diisobutyl ketone, cyclohexanone), ethers (e.g. ethyl ether, dioxane, cellosolve, dipropyl) 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, diisopropylphthalate,
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,
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, Bran oil, bentonite, lignin sulfonate, etc. For the purpose of improving the flowability 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 amount of active ingredients may be adjusted as necessary. Usually 0.5 to 20% (by weight) when used as a powder or granule, or 0.1% when used as an emulsion or wettable powder.
~50% (by weight) is suitable. 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 foliage or soil on the weeds or in areas where the emergence or growth of the weeds is not desirable. 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 10 to 500 g per 10 ares. When mixed with
Considering that in many cases, the compound of the present invention is effective at a lower dose than when used alone, the dosage of the compound of the present invention can be selected from an even smaller range. The herbicide of the present invention is particularly valuable as a pre-emergence or early-emergence treatment agent in fields or as an early to mid-stage herbicide in paddy fields, but it can also be used to expand the target grass species and the suitable period for control, or to reduce the dosage. Therefore, it is also possible to use the herbicide in combination with other herbicides, which falls within the scope of the present invention. For example, phenoxy fatty acid herbicides such as 2,4-PA (e.g. ethyl 2,4-dichlorophenoxyacetate), MPC (e.g. ethyl 2-methyl-4-chlorophenoxyacetate, sodium 2-methyl-4-chlorophenoxyacetate, −
allyl methyl-4-chlorophenoxyacetate),
MCPB (ethyl 2-methyl-4-chlorophenoxybutyrate): diphenyl ether herbicide e.g.
NIP (2,4-dichlorophenyl-4'-nitrophenyl ether), CNP (2,4,6.trichlorophenyl-4'-nitrophenyl ether), chromethoxynil (2,4-dichlorophenyl-3-methoxy- 4'-nitrophenyl ether); s-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]: Carbamate herbicides such as molinate (s-ethylhexahydro-1H
-Azepine-1-carbothioate), MCC [methyl-N-(3,4-dichlorophenyl)-carbamate], IPC [isopropyl-N-(3-chlorophenyl)carbamate], benthicamine [s
-(4.Chlorbenzyl)-N,N'-dimethylthiocarbamate]; Others DCPA (3,4-dichloropropionanilide),
Butachlor [2-chloro-2',6'-diethyl-N-(butoxymethyl)-acetanilide], Alachlor [2-chloro-2',6'-diethyl-N
-(methoxyethyl)acetanilide], bentazone (3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide), trifluralin (α,α,α-trifluoro-2,6 −
dinitro-N,N-dipropyl-p-toluidine), MCMU[3-(3,4-dichlorophenyl)
-1,1-dimethylurea] and other herbicides in combination with one or more herbicides. The abbreviation is based on the ``Pesticide Handbook - 1978'' published by the Plant Protection Association. Some test examples, examples, and reference examples of the present invention are shown below, but the present invention is not limited to these. Test Example 1: Effect on paddy field weeds before budding Fill a 1/10,000th R pot with soil to make it into a paddy field, and remove 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. After 21 days of 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 but less than 100% weed killing 3...80% or more but less than 90% weed killing 2...70% or more but less than 80% weed killing 1...70 Less than % weed killing The results are shown in Table 2.

【table】

[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 25-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: Nobie, 1-leaf stage, Konagi, 2-3 leaf stage, Cyperus 1-2 leaf stage, Firefly, 2-3 leaf stage, Urikawa, 3 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.

【table】

[Table] Test Example 3: Effect on upland weeds before they emerge Fill a polyethylene bucket measuring 10cm x 20cm x 5cm deep with soil, and sow upland weeds such as oats, wild grasses, crabgrass, blueberry, mugwort, snail, and staghorn. did. 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.

【table】

[Table] Test Example 4: Effect on field weeds after germination In a polyethylene pot 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 the leaf stage shown below. 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 weeds and their leaf stages and soybean leaf stages Oat Two-leaf grasshopper Two-leaf Aobifolia One-leaf mugwort One-leaf Japanese grass 2-leaf stage Japanese cypress One-leaf stage Soybean First compound leaf stage Judgment criteria for herbicidal activity and criteria for chemical damage were based on Test Examples 1 and 2, respectively. The results are shown in Table 5.

【table】

[Table] Example 1 Compound No. 4 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. Example 2 Compound No. 23 5 parts Bentonite clay mixture 90 parts Calcium lignin sulfonate 5 parts were uniformly mixed and ground, and an appropriate amount of water was added, kneaded well, and granulated. Example 3 Compound No. 25 50 parts xylene 40 parts A mixture of polyoxyethylene nonyl phenyl ether and calcium alkylbenzenesulfonate 10 parts were uniformly mixed to form an emulsion.

Claims (1)

[Claims] 1 General formula () (wherein, X represents a halogen atom, R ¹ represents an alkyl group having 1 to 4 carbon atoms, Y represents a hydrogen atom, an alkyloxy group having 1 to 4 carbon atoms,
Alkenyloxy group having 2 to 4 carbon atoms, alkynyloxy group having 3 to 4 carbon atoms, halomethyloxy group, haloethyloxy group, alkyloxycarbonylalkyl group in which the total number of carbon atoms in the alkyl group is 3 to 6. Represents a phenylalkyloxy group in which the oxy group or alkyl group has 1 to 4 carbon atoms, and R ² is 1 to 4 carbon atoms.
to 4 alkyl group, halomethyl group or haloethyl group. However, in the above definitions ^of Y, R ² and In the case of 2 to 4 alkenyloxy groups,
R ² is a haloethyl group, and X is a chlorine atom,
When Y is an alkynyloxy group having 3 to 4 carbon atoms or a phenylalkyloxy group having 1 to 4 carbon atoms,
R ² represents a halomethyl group, and when Y is a halomethyloxy group or a haloethyloxy group, R ² is an alkyl group having 1 to 4 carbon atoms,
When Y represents a halomethyl group or a haloethyl group and Y is an alkyloxycarbonylalkyloxy group in which the total number of carbon atoms in the alkyl group is 3 to 6, R ² is a halomethyl group and X represents a chlorine atom. do. ) Δ ² -1,2,4-triazoline-
A herbicide containing 5-ones as an active ingredient.