JPH053442B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a herbicidal composition characterized by containing an N-substituted chloroacetanilide and an amide derivative as active ingredients. The following four properties are essentially required of herbicides. First, it must be safe for crops; second, it must have a broad herbicide spectrum necessary to completely kill the many types of weeds that grow in crop-growing areas; and third, it must be safe for crops. Fourth, it has long-lasting efficacy and, fourth, it has more effective herbicidal action when applied in small amounts. The present inventors have conducted extensive research with the aim of developing an excellent herbicide that satisfies the above properties, and have obtained the following general formula [] (However, in the formula, A represents a halogen atom, an alkoxy group, or an alkylthio group, and R ₁ , R ₂ and
We have already proposed an N-substituted chloroacetanilide represented by (R ₃ represents the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group, or alkylthio group) (Japanese Patent Application No. 111077/1983).
issue). The present inventor further found that a herbicidal composition containing an N-substituted-chloroacetanilide represented by the above general formula [] and a specific amide derivative as active ingredients,
It was discovered that each compound exhibits a synergistic effect that could not be expected from their individual properties, that is, they have a wide herbicidal spectrum at low doses. Based on these new findings, the present inventors have completed and proposed the present invention. That is, the present invention provides the following general formula [] (However, in the formula, A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively. , represents an alkylthio group) and the following general formula [] (However, R ₄ is an alkyl group, X is a halogen atom,
Y ₁ and Y ₂ are the same or different hydrogen atoms, respectively;
It is a halogen atom, an alkyl group, or an alkoxy group. ) as an active ingredient. One component of the herbicidal composition of the present invention is an N-substituted chloroacetanilide represented by the following general formula []. (However, in the formula, A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively. , represents an alkylthio group) In the N-substituted chloroacetanilide represented by the above general formula [], A is a hydrogen atom or an alkyl group, R ₁ is an alkyl group, and R ₂ is a hydrogen atom, an alkyl group, or an alkyl group. is an alkoxy group,
Compounds in which R ₃ is a hydrogen atom, an alkyl group or a halogen atom are known from US Pat. No. 3,901,917. However, most of the others are new compounds. In the general formula [], specific examples of the halogen atoms represented by A, R ₁ , R ₂ and R ₃ include chlorine, bromine, fluorine and iodine atoms. In the above general formula [], the alkoxy group represented by A, R ₁ , R ₂ and R ₃ is not particularly limited, but is generally a linear or branched saturated or unsaturated group having 1 to 6 carbon atoms. groups are preferred. Specific examples of the alkoxy group that are generally preferably used include methoxy group, ethoxy group, n-propoxy group, t-
Examples include butoxy group, n-pentoxy group, n-hexoxy group, allyloxy group, and the like. In the above general formula [], the alkylthio groups represented by A, R ₁ , R ₂ and R ₃ are not particularly limited and known ones can be used, but generally have 1 to 6 carbon atoms.
Straight-chain or branched saturated or unsaturated groups are preferred. Specific examples of the alkylthio group that are preferably used include methylthio group, ethylthio group, n-propylthio group, t-butylthio group, n-pentylthio group, n-hexylthio group,
Examples include allylthio group. Furthermore, in the above general formula [], the alkyl groups represented by A, R ₁ , R ₂ and R ₃ are not particularly limited and any known alkyl group can be used, but they are generally straight chain groups having 1 to 6 carbon atoms. Suitable are saturated or unsaturated groups that are shaped or branched. Specific examples of the alkyl group that are generally preferably used include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-
Butyl group, t-butyl group, n-pentyl group, n-
Examples include hexyl group, allyl group, and ethynyl group. The structure of the N-substituted-chloroacetanilide represented by the general formula [] can be confirmed by the following means. (b) By measuring the infrared absorption spectrum (IR), it is possible to observe absorption based on the CH bond in the vicinity of 3150 to 2800 cm ^-1 and characteristic absorption based on the carbonyl bond of the amide group in the vicinity of 1680 to 1670 cm ^-1 . I can do it. (b) Measure the mass spectrum (ms) and calculate the composition formula corresponding to each observed peak (generally expressed as m/e, which is the ion mass number m divided by the ion charge number e). Accordingly, it is possible to know the molecular weight of the compound subjected to measurement and the bonding mode of each atomic group within the molecule. In other words, the sample subjected to measurement is expressed by the general formula [] When expressed as The molecular weight of can be determined. Furthermore, regarding the N-substituted-chloroacetanilide represented by the general formula [], M-C1, M-
COCH ₂ C1 and

A characteristic strong peak corresponding to [Formula] is observed, and the bonding mode of the molecule can be known. (c) 1H-nuclear magnetic resonance spectrum (1H-NMR)
By measuring , it is possible to know the bonding mode of hydrogen atoms present in the N-substituted chloroacetanilide represented by the general formula []. 1H-NMR (δ, ppm:
(based on tetramethylsilane, in deuterated chloroform solvent), N-[2'-(5'-bromo)
-thienylmethyl]-N-chloroaceto-2,
The 1H-NMR diagram of 6-dimethylanilide is shown in Figure 1. The analysis results are as follows. In other words, a singlet corresponding to 6 protons was observed at 2.0 ppm, and 2 and 6 protons of the phenyl group
It can be attributed to the methyl group (d) substituted at position. A singlet corresponding to two protons was observed at 3.6 ppm, and can be attributed to the methylene group (h) in the chloroacetyl group. A singlet corresponding to two protons was observed at 4.57 ppm, and can be attributed to the methylene group (c). A quartet corresponding to two protons was observed at 6.67ppm,
This can be attributed to protons (a) and (b) substituted on the thiophene ring. A multiplet corresponding to three protons was observed at 6.95 to 7.30 ppm, and can be attributed to protons (e), (f), and (g) substituted with phenyl groups. To summarize the 1H-NMR characteristics of the N-substituted-chloroacetanilide represented by the above general formula [], the methylene proton of the chloroacetyl group is usually a singlet around 3.6 to 3.8 ppm, and the methylene proton of the aminomethylene group is a singlet at around 4.8 ppm (however, it may appear as a double line if there is an asymmetric substituent at the 2 and 6 positions on the aniline side), and the proton on the thiophene ring side is at 5.8 to 5.8 ppm. At 7.4 ppm, protons on the benzene side tend to show a characteristic peak at 6.0 to 7.7 ppm. (d) Calculate the weight percent of oxygen by determining the weight percent of each of carbon, hydrogen, nitrogen, sulfur, and halogen by elemental analysis, and then subtracting the sum of the weight percent of each recognized element from 100. is possible,
Therefore, the compositional formula can be determined. In addition, N-substituted-chloroacetanilide is
Although its properties differ somewhat depending on the types of A, R ₁ , R ₂ , and R ₃ in the above general formula [], it is generally a pale yellow or yellow viscous liquid or solid at room temperature and normal pressure, and is extremely Many have high boiling points. More specifically, as shown in the synthesis examples described later, the boiling point of the above compound tends to increase as the molecular weight increases, like general organic compounds. The compound is soluble in common organic solvents such as benzene, ether, alcohol, chloroform, carbon tetrachloride, acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide, but almost insoluble in water. The method for producing the N-substituted chloroacetanilide represented by the general formula [] is not particularly limited. A typical manufacturing method is described below. general formula (However, A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, or alkylthio groups, respectively. A compound represented by the general formula [ ] is reacted with a chloroacetyl halide represented by the general formula ClCH ₂ COX (where X represents a halogen atom). N-substituted-chloroacetanilide can be obtained. The aniline derivative represented by the above general formula [], which is a raw material, can be obtained by any method. In the reaction between the compound represented by the above general formula [] and chloroacetyl halide, the molar ratio of both compounds may be appropriately determined as necessary, but it is usually the same molar ratio or a slightly excess molar amount of chloroacetyl halide. It is common to use Further, in the above reaction, hydrogen halide is produced as a by-product. This hydrogen halide reacts with the compound represented by the general formula [] in the reaction system, causing a decrease in the yield of the product, so it is usually not recommended to coexist with a hydrogen halide scavenger in the reaction system. preferable. The hydrogen halide scavenger is not particularly limited, and any known one can be used. Examples of the scavenger that are generally suitably used include trialkylamines such as trimethylamine, triethylamine, and tripropylamine, pyridine, sodium alcoholate, and sodium carbonate. It is generally preferable to use an organic solvent in the reaction. Examples of solvents preferably used include benzene, toluene, xylene,
Aliphatic or aromatic hydrocarbons or halogenated hydrocarbons such as hexane, heptane, petroleum ether, chloroform, and ethylene chloride; Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Acetonitrile, etc. Nitriles;
Examples include N,N-dialkylamides such as N,N-dimethylformamide and N,N-diethylformamide; dimethylsulfoxide and the like. The order of addition of the raw materials in the reaction is not particularly limited, but generally, the compound represented by the general formula [] is dissolved in a solvent, charged into a reactor, and the chloroacetyl halide dissolved in the solvent is added under stirring. good. Of course, it is also possible to continuously add raw materials to the reaction system and take out the produced reactants continuously from the reaction system. The temperature in the reaction can be selected from a wide range, generally -20°C to 150°C, preferably 0°C to 120°C.
It is sufficient to choose from the range of ℃. Reaction time varies depending on the type of raw material, but is usually 5 minutes to 10 days.
Preferably, it is sufficient to select from the range of 1 to 40 hours. Further, during the reaction, it is preferable to perform stirring. The method for isolating and purifying the desired product, ie, the N-substituted chloroacetanilide represented by the above general formula [], from the reaction system is not particularly limited, and any known method can be employed. For example, the reaction solution is cooled or allowed to cool naturally to return to room temperature or near room temperature, the reaction solvent and the remaining hydrogen halide scavenger are distilled off, and the residue is extracted with benzene. In the above operation, the salt and high molecular weight compound produced from the by-produced hydrogen halide and the hydrogen halide scavenger are separated. The benzene layer is dried with a desiccant such as Glauber's salt or calcium chloride, and then benzene is distilled off and the residue is vacuum distilled to obtain the desired product.
In addition to isolation and purification by vacuum distillation, it can also be produced by purification by chromatography, or if the product is a solid, by recrystallization from a solvent such as hexane. Furthermore, the general formula (However, A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and X represents a halogen atom.) 2-substituted thiophene represented by the general formula (However, R ₁ , R ₂ and R ₃ represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, and alkylthio groups.) An N-substituted-chloroacetanilide represented by the formula [] can be obtained. The 2-substituted thiophene and the chloroacetanilide used as raw materials can be obtained by any method. In addition, the conditions and isolation and purification method for carrying out this reaction are almost the same as those used in the reaction of the compound represented by the general formula [] with chloroacetyl halide as described above. Conditions can be adopted. The N-substituted chloroacetanilide represented by the above general formula [] has a wide herbicidal spectrum against annual weeds such as field weeds and cogina that occur in paddy fields, as well as perennial weeds such as firefly, cypress, omodaka, and urikawa. It is an excellent herbicide that can efficiently control paddy rice without causing chemical damage. In particular, it has an outstanding herbicidal activity unparalleled by other herbicides, even when sprayed in a very small amount, against the perennial cypress, which has become a problem in recent years. General formula [] (However, R ₄ is an alkyl group, X is a halogen atom,
Y ₁ and Y ₂ are the same or different hydrogen atoms, respectively;
It is a halogen atom, an alkyl group, or an alkoxy group. ) is an amide derivative represented by In the above general formula [], the alkyl groups represented by R ₄ , Y ₁ and Y ₂ are not particularly limited in the number of carbon atoms, and any group can be used. Among these, those having 1 to 4 carbon atoms are preferred. Suitable alkyl groups in the present invention include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl groups. Further, in the above general formula [], the number of carbon atoms of the alkoxy groups represented by Y ₁ and Y ₂ is not particularly limited, but those having 1 to 4 carbon atoms are preferred from the viewpoint of easy availability of raw materials. Suitable alkoxy groups in the present invention include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, and t-butoxy groups. Further, in the above general formula [], the halogen atoms represented by X, Y ₁ and Y ₂ include fluorine, chlorine, bromine, and iodine atoms. Among the amide derivatives represented by the above general formula [], those in which Y ₁ and Y ₂ are hydrogen atoms and X is a bromine atom are preferably used because they have particularly high herbicidal activity. As a method for producing the amide derivative represented by the above general formula [], any known production method can be employed without any restriction. The amide derivative represented by the general formula [] is
It is known to have a strong growth control effect on paddy field weeds belonging to the Cyperaceae family, such as Cyperus japonica, Cyperus japonica, and Cyperus japonica, and it is said that it always shows a stable herbicidal effect on Cyperus japonica, regardless of the depth of its infestation. have a property. The herbicidal composition of the present invention provides excellent herbicidal effects over a wide range of usage ratios of the N-substituted chloroacetanilide represented by the above general formula [] and the amide derivative represented by the above general formula []. However, the ratio of the amide derivative to 1 part by weight of N-substituted chloroacetanilide is 0.01 part by weight.
It is generally in the range of ~50 parts by weight. More preferably, by using 1 to 20 parts by weight of the amide derivative per 1 part by weight of the N-substituted chloroacetanilide, the herbicidal effect becomes even more excellent. When the herbicide composition of the present invention is used against wildflowers and paddy rice that are sown at the same time in paddy soil, the germination of wildflowers treated at a concentration of 0.1g per are is completely inhibited, but when paddy rice is treated with 100g. Even if you do, there will be no effect at all. Therefore, it is generally sufficient to use the active ingredient in paddy fields in an amount of 0.15 to 200 g, preferably 0.5 to 50 g per are. The herbicide composition of the present invention is effective even when treated before and after weed germination, and is highly effective in soil treatment and foliage treatment. It is useful in a wide range of areas where it can be applied, including rice fields, fields of various grains, legumes, cotton, vegetable crops, orchards, lawns, pastures, tea gardens, mulberry gardens, forests, non-agricultural lands, etc. . The herbicidal composition of the present invention may be sprayed as a raw material itself, or may be sprayed as a preparation prepared by mixing it with a carrier and, if necessary, other adjuvants. The formulation form is not particularly limited, and conventionally known formulation forms can be used. For example, it can be prepared and used in powders, coarse powders, fine granules, powders, wettable powders, emulsions, flowable preparations, oil suspensions, and the like. When preparing the herbicidal composition of the present invention into a formulation, any conventionally known solid carrier can be used without any restriction as an appropriate solid carrier. Examples of solid carriers preferably used in the present invention are as follows. For example, clays represented by kaolinite group, montmorillonite group, attapulgite group, ziecrite, etc.; talc, mica, phyllite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth magnesium, lime, phosphorus. Ashite, zeolite, silicic anhydride,
Inorganic substances such as synthetic calcium silicate; vegetable organic substances such as soybean flour, tobacco powder, walnut flour, wheat flour, wood flour, starch, and crystalline cellulose; chroman resin, petroleum resin, alkyd resin, polyvinyl chloride,
Synthetic or natural polymer compounds such as polyalkylene glycol, ketone resin, ester gum, copal gum, and dammar gum; waxes such as carnauba wax and beeswax; and urea. Further, as the liquid carrier used in the present invention, conventionally known carriers can be used without any restriction. Examples of liquid carriers preferably used in the present invention are as follows. kerosene, mineral oil,
Paraffinic or naphthenic hydrocarbons such as spindle oil and white oil; Aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene; carbon tetrachloride, chloroform, trichloroethylene, monochlorobenzene, o-chlorotoluene Chlorinated hydrocarbons such as dioxane, ethers such as tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, diethylene glycol acetate, maleic Esters such as dibutyl acid and diethyl succinate; Alcohols such as methanol, n-hexanol, ethylene glycol, and diethylene glycol; Ether alcohols such as ethylene glycol phenyl ether, diethylene glycol ethyl ether, and diethylene glycol butyl ether; dimethyl formamide, dimethyl sulfoxide, etc. Examples include polar solvents such as water and water. In addition, the preparation of the formulation in the present invention includes emulsification,
Conventionally known surfactants can be used without any restriction for purposes such as dispersion, wetting, mineral expansion, binding, disintegration control, active ingredient stabilization, fluidity improvement, and rust prevention. As the surfactant, nonionic, cationic, anionic and amphoteric surfactants can be used, and usually nonionic and/or anionic surfactants are used. Suitable nonionic surfactants include, for example, those obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; and those obtained by polymerizing and adding ethylene oxide to alkyl phenols such as isooctylphenol and nonylphenol. ethylene oxide is polymerized and added to alkyl phenols such as isooctylphenol and nonylphenol; ethylene oxide is polymerized and added to alkylnaphthols such as butylnaphthol and octylnaphthol; palmitic acid, stearic acid, oleic acid, etc. Products obtained by polymerizing and adding ethylene oxide to higher fatty acids; Products obtained by polymerizing and adding ethylene oxide to mono- or dialkyl phosphoric acids such as stearyl phosphoric acid and dilauryl phosphoric acid; Products obtained by polymerizing and adding ethylene oxide to amines such as dodecylamine and stearic acid amide. Examples include higher fatty acid esters of polyhydric alcohols such as sorbitan and those obtained by polymerizing and adding ethylene oxide to them; those obtained by polymerizing and adding ethylene oxide and propylene oxide; and esters of polyhydric fatty acids and alcohols such as dioctyl succinate. Suitable anionic surfactants include, for example, alkyl sulfate salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonate salts such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate. ; Aryl sulfonates such as sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzenesulfonate; and phosphates such as sodium tripolyphosphate. Furthermore, in the formulation of the present invention, conventionally known adjuvants can be used without any restrictions. Adjuvants are used for various purposes, and are also used, for example, when attempting to enhance the herbicidal effect by improving properties such as disintegration of granules. Examples of adjuvants suitably used in the present invention are as follows. casein, gelatin, albumin, glue,
Examples include polymeric compounds such as sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose, and polyvinyl alcohol. The above-mentioned carrier, surfactant, and adjuvant are used individually or in combination as appropriate depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc. The method for preparing the formulation in the present invention is not particularly limited, and conventionally known methods can be used. For example, one specific method for preparing a wettable powder is to dissolve 10 parts by weight of an amide derivative and 1 part by weight of N-substituted chloroacetanilide in an organic solvent, add a surfactant and a carrier to the solution, and then thoroughly pulverize and mix. There is a method of obtaining a wettable powder by removing the organic solvent. For example, as a specific method for preparing an emulsion, an emulsion is obtained by thoroughly mixing 10 parts by weight of an amide derivative, 5 parts by weight of an N-substituted chloroacetanilide, and 15 parts by weight of a surfactant in a petroleum solvent such as xylene. There is a way. Furthermore, as a specific method for preparing granules, for example, 10 parts by weight of an amide derivative, 1 part by weight of N-substituted chloroacetanilide, a surfactant and water are thoroughly kneaded, and then a carrier and a surfactant are added. Add, stir well, and extrude to the specified particle size.
There is a method of obtaining granules by drying. The herbicidal composition of the present invention described above exhibits a herbicidal effect that cannot be expected from the properties of each component alone. That is, it has a broad herbicidal spectrum.
Furthermore, it has a greater herbicidal effect at the same level as the application amount of each component alone. Moreover, it is safe for crops. Therefore, the herbicidal composition of the present invention fully satisfies the properties required of a herbicide and is extremely useful. EXAMPLES The herbicidal composition of the present invention will be specifically explained below using Examples, but the present invention is not limited to these Examples. Synthesis of N-substituted-chloroacetanilide (Synthesis Example 1) N-[2'-(5'-bromo)-thienylmethyl]-
2,6-dimethylaniline 1.81g (6.14×10 ^-3
mole) was dissolved in 40 ml of benzene, 0.81 g (7.98 x 10 ^-3 mole) of triethylamine was added, and the mixture was placed in ice water. Then 0.83g of chloroacetyl chloride
(7.37×10 ^-3 mole) in benzene solution (15 ml) was gradually added. After stirring for 3 hours, the mixture was heated at 50°C for 1 hour. After cooling the reaction mixture to room temperature,
It was washed successively with 50 ml of water, 50 ml of 2N hydrochloric acid, and then 50 ml of water, and the benzene layer was dried over anhydrous sodium sulfate. Thereafter, it was purified by column chromatography to obtain 1.13 g of a yellow solid. As a result of measuring the infrared spectrum of this product, it showed an absorption based on the C-H bond at 3110 to 2900 cm ^-1 and a strong absorption based on the carbonyl bond of the amide group at 1670 cm ^-1 . Its elemental analysis value is
C48.43%, H4.05%, N3.99%, _{C15 H15}
C48.20 is the calculated value for NSOBrCl (372.71)
%, H4.32%, and N3.75%. In addition, when mass spectra were measured, m/
Molecular ion peak corresponding to molecular weight at e371,
M, peak corresponding to M−Cl at m/e336,
A peak corresponding to M−COCH ₂ Cl at m/e293,
m/e143 (100%) Each corresponding peak is shown. Furthermore, regarding the 1H-nuclear magnetic resonance spectrum,
This is as shown as a specific example in the specification. From the above results, it is clear that the isolated product is N-[2'-(5'-
bromo)-thienylmethyl]-N-chloroaceto-
It became clear that it was 2,6-dimethylanilide (hereinafter abbreviated as compound (1)). The yield is N
-[2'-(5'-bromo)-thienylmethyl]-2,6
−49.5% (3.04×10 ^-3 for dimethylaniline)
mole). (Synthesis Example 2) The properties, physical properties (boiling point), characteristic absorption values in the infrared absorption spectrum, and elemental analysis results of N-substituted-chloroacetanilide synthesized in the same manner as in Synthesis Example 1 are summarized in Table 1. General formulas in Table 1 is the general formula [] Corresponding to, D is

[Formula], B is

[Formula] means.

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[Table] Next, formulation examples and examples of the herbicide composition of the present invention are shown. In addition, in the formulation examples and examples, N-substituted-chloroacetanilides are represented by compound numbers [(1) to (52)] in the synthesis examples, and amide derivatives are represented by the following symbols ([A] to [I]). expressed.

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[Table] Formulation example 1 10 parts by weight of compound [A], 1 part by weight of compound (1), surfactant Solpol 800A [trademark of Toho Chemical Industry Co., Ltd.]
1.5 parts by weight, 1.5 parts by weight of surfactant Detargent 60 (trademark of Lion Yushi Co., Ltd.) and Siegrite 86
Parts by weight were thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 10 parts by weight of compound [A], 5 parts by weight of compound (10), 15 parts by weight of surfactant Solpol SM100 (trademark of Toho Chemical Industries, Ltd.) and 70 parts by weight of xylene were thoroughly mixed to obtain an emulsion. . Formulation Example 3 10 parts by weight of compound [A], 1 part by weight of compound (20), 4 parts by weight of dioctyl succinate, 4 parts by weight of sodium tripolyphosphate, 41 parts by weight of bentonite and 40 parts by weight of talc were thoroughly mixed and ground, and mixed with water. After adding and kneading, the mixture was granulated and dried, and the granules were sized to 14 to 32 mesh to obtain granules. Formulation example 4 40 parts by weight of bentonite, 55 parts by weight of talc, and 5 parts by weight of sodium tripolyphosphate were ground and mixed,
After adding water and kneading, the mixture is granulated and dried to produce granules that do not contain active ingredients. Add compound [A] to 85 parts by weight of this granular material.
The mixture was impregnated with 10 parts by weight of compound (30) and 5 parts by weight of compound (30) to obtain granules. Example 1 A Wagner pot equivalent to 1/5000 are is filled with water-mixed paddy soil, seeds of broad-leaved weeds such as Japanese grasshopper, Japanese cypress, firefly, and broad-leaved weeds such as cypress, azalea, and cypress are sown on the surface layer of the soil, and tubers of Japanese cypress and Japanese cypress are sown. embedded. moreover
Three rice seedlings (variety name: Akinishiki) at the 2.5 leaf stage were planted at a depth of 2 cm. After that, the rice was submerged in water to a depth of about 3 cm, and grown in a glass room at 20 to 25°C, and 7 days after transplanting (when the rice plants were at about 0.8 leaf stage) and 14 days later.
After a few days (when the wildflowers were at about the two-leaf stage), the wettable powder prepared according to Formulation Example 1 was diluted with water and a predetermined amount was dropped. After that, they are grown in a glass room and treated with chemicals.
On the 21st day, the herbicidal effect and the chemical damage to paddy rice were investigated. The results are shown in Table 2. Weeding effect Paddy rice chemical damage Weed suppression rate (%) −: Normal 5:100 (complete death) ±: Slight damage 4: 75-99 +: Slight damage 3: 50-74: Medium damage 2: 25-49 1: 1- 24 0:0 (no effect observed at all)

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【table】 [Brief explanation of the drawing]

FIG. 1 shows a 1H-NMR chart of N-substituted-chloroacetanilide obtained in Synthesis Example 1.

Claims (1)

[Claims] Linear formula (However, in the formula, A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively. , represents an alkylthio group) and the following formula: (However, R ₄ is an alkyl group, X is a halogen atom,
Y ₁ and Y ₂ are the same or different hydrogen atoms, respectively;
It is a halogen atom, an alkyl group, or an alkoxy group. ) A herbicidal composition comprising an amide derivative represented by the following as an active ingredient.