JPS60218302A - Herbicide composition - Google Patents

Abstract

PURPOSE:The titled composition contains an N-substituted chloroacetanilide and an amide derivative as active components, exhibits broad herbicidal spectrum at a low rate of application, is effective to the treatment of the fields and orchards of various crops, beans, cotton, etc., and is safe to the crops. CONSTITUTION:The objective composition contains the N-substituted chloroacetanilide of formula I (A is H, halogen, alkyl, alkoxy or alkylthio; R1, R2 and R3 are H, halogen, alkyl, alkoxy or alkylthio) and the amide derivative of formula II (R4 is alkyl; X is halogen; Y1 and Y2 are H, halogen, alkyl or alkoxy), as active components. The amount of the amide derivative is 0.01-50pts.(wt.), preferably 1-20pts. per 1pt. of the compound of formula I . It can be scattered without dilution or as a mixture with a carrier or adjuvant the applied in the form of powder, emulsifiable concentrate, etc.

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. Firstly, it must be safe for crops; secondly, it must have a broad herbicidal spectrum necessary to completely kill the wide variety of weeds that grow in crop-growing areas; and thirdly, it must be a weed killer. that the efficacy of the agent lasts for a long time;
Fourthly, 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 properties described above, and have developed the following general formula (I) (wherein A represents a halogen atom, an alkoxy group, or an alkylthio group). R+, R2, and R2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, and alkoxy groups, respectively.

We have already proposed an N-substituted chloroacetanilide represented by (representing an alkylthio group).
No. 7〉. The present inventors have generally found that a herbicide composition containing an N-substituted-chloroacetanilide represented by the above general formula (1) and a specific amide derivative as active ingredients exhibits a synergistic effect that could not be expected from the properties of each alone. to manifest an effect,
In other words, it has been found that it has 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 (1) (However, in the formula, A is a hydrogen atom or a halogen atom.

An N-substituted chloroacetanilide represented by the following general formula (II) (wherein R4 is an alkyl group, X is a halogen atom, and R4 is an alkyl group, X is a halogen atom, Yl and Yl are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively.

One component of the herbicide composition of the present invention has the following general formula (
1') is an N-substituted chloroacetanilide.

R1 (However, in the formula, A is a hydrogen atom or a halogen atom.

represents an alkyl group, an alkoxy group, or an alkylthio group, and R+, R2, and R3 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups,
Indicates an alkylthio group.

) Among the N-substituted chloroacetanilides represented by the above general formula CI), A is a hydrogen atom or an alkyl group, and R
1 is an alkyl group, R2 is a hydrogen atom, an alkyl group, or an alkoxy group, and R3 is a hydrogen atom, an alkyl group, or a halogen atom.
No. 1917. However, most of these are new compounds.

In the general formula (1), specific examples of the halogen atoms represented by A, R+, R2, and R3 include chlorine, bromine, fluorine, and iodine atoms. In the general formula (I), the alkoxy groups represented by A, R+, R2 and R3 are not particularly limited, but are generally preferably linear or branched saturated or unsaturated groups having 1 to 6 carbon atoms. It is. Specific examples of the alkoxy group that are generally preferably used include methoxy group, ethoxy group, n-propoxy group, t-butoxy group, rl-pentoxy group, n-hexoxy group, allyloxy group, and the like.

In the general formula (I), the alkylthio groups represented by A, R+, R2, and R3 are not particularly limited, and known ones can be used, but they are generally linear or branched groups having 1 to 6 carbon atoms. Saturated or unsaturated groups are preferred. Specific examples of the alkylthio group that are preferably used include methylthio group, ethylthio group, and n-propylthio group.

Examples include t-butylthio group, n-pentylthio group, n-hexylthio group, and allylthio group.

Furthermore, in the general formula (I), A, Rs, R2 and R
The alkyl group represented by 3 is not particularly limited and any known alkyl group can be used, but a linear or branched saturated or unsaturated group having 1 to 6 carbon atoms is generally preferred.

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, 1so-butyl group.

Examples include t-butyl group, n-pentyl group, n-hexyl group, allyl group, and ethynyl group.

The structure of the N-substituted chloroacetanilide represented by the general formula (I) can be confirmed by the following means.

(b) By measuring the infrared absorption spectrum (IR), it is possible to observe a characteristic absorption based on the CH bond in the vicinity of 3150 to 2800 cm'', and a characteristic absorption based on the carbonyl bond of the amide group in the vicinity of 1680 to 1670 cm'. I can do it.

[Note] Measure the mass spectrum (ms) and calculate each peak observed (generally, the ion mass number m is expressed as the ion charge number e).
By calculating the composition formula corresponding to the value expressed by m/e divided by m/e, 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. That is, when a sample subjected to measurement is represented by the general formula (I), a molecular ion peak (hereinafter abbreviated as Me) is generally contained in the molecule! Since the intensity ratio is observed according to the isotope abundance ratio depending on the number of halogen atoms present, the molecular weight of the compound subjected to measurement can be determined. Furthermore, for the N-substituted-chloroacetanilide represented by the general formula (I), characteristic strong peaks corresponding to MΦ-C1 and MΦ are observed, allowing the bonding mode of the molecule to be known.

(c> IH-Nuclear Magnetic Resonance Spectrum (IH-NMR)
By measuring >, it is possible to know the bonding mode of the hydrogen atoms present in the N-substituted chloroacetanilide represented by the general formula (I). I H-N of N-substituted-chloroacetanilide represented by the general formula CI)
As a specific example of MR (δ, ppI: in a 9-fold chloroform solvent based on tetramethylsilane), I H
-The NMR diagram is shown in FIG. The analysis results are as follows.

(k'') That is, a singlet corresponding to 6 protons was observed at 2.0 ppm, and it can be attributed to the methyl group (d) substituted at the 2 and 6 positions of the phenyl group. A singlet corresponding to two protons was observed, and it 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 the methylene group (h) was observed at 4.57 ppm.
It can be attributed to C). A quartet corresponding to two protons was observed at 6.67 ppm, and can be attributed to protons (a) and (b) substituted on the thiophene ring. A weight line corresponding to three protons was observed at 6.95 to 7.30 ppm, and can be attributed to protons (, e), (f), and ((J) substituted with phenyl groups.

To summarize the I H-NMR characteristics of the N-substituted-chloroacetanilide represented by the general formula (I) above, the methylene proton of the chloroacetyl group is usually a singlet around 3.6 to 3.8 ppm, and the amino The methylene proton of the methylene group is a single line at around 4.8 ppm (however, if there is an asymmetric substituent at the 2 and 6 positions on the aniline side, it may appear as a double line)
The protons on the thiophene ring side tend to show characteristic peaks at 5.8 to 7.4 ppm, and the protons on the benzene side tend to show characteristic peaks at 6.0 to 7.7 ppm.

(d) Carbon, hydrogen, and nitrogen by elemental analysis.

The weight percent of oxygen can be calculated by subtracting from 100 the sum of the weight percent of each element and the weight percent of each recognized element, and thus:
The compositional formula can be determined.

In addition, N-substituted-chloroacetanilide includes A, R1゜R21 and R3 in the general formula (I).
Although its properties differ somewhat depending on the type, it is generally a pale yellow or yellow viscous liquid or solid at normal temperature and pressure, and many have extremely 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 compounds include benzene, ether, alcohol, chloroform, carbon tetrachloride, acetonitrile lNlN
-Soluble in common organic solvents such as dimethylformamide and dimethyl sulfoxide, but almost insoluble in water.

The method for producing the N-substituted chloroacetanilide represented by the general formula (I) is not particularly limited. A typical manufacturing method is described below.

General formula (where A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and R1', R2, and R3 are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively) , represents an alkylthio group) and the compound represented by the general formula CI CH2C0X (where X represents a halogen atom).

) The N-substituted-chloroacetanilide represented by the general formula (I) can be obtained by reacting with the chloroacetyl halide represented by the formula (I).

The aniline derivative represented by the general formula (III) as a raw material can be obtained by any method.

In the reaction between the compound represented by the general formula (III) and chloroacetyl halide, the molar ratio of both compounds to be charged may be appropriately determined as necessary, but it is usually the same molar ratio or a slight excess molar amount of chloroacetyl halide. It is common to use

Further, in the above reaction, hydrogen halide is produced as a by-product. Since this hydrogen halide reacts with the compound represented by the general formula (1) in the reaction system and causes a decrease in the yield of the product, a halogenated hydrogen scavenger is usually coexisted in the reaction system. It is 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 alcoholade, and sodium carbonate.

It is generally preferable to use an organic solvent in the reaction. Examples of solvents preferably used include benzene, toluene, xylene, hexane, heptane, petroleum ether, and chloroform.

Aliphatic or aromatic hydrocarbons or halogenated hydrocarbons such as ethylene chloride; ethers such as diethyl ether, dioxane, and tetrahydrofuran; acetone;
Ketones such as methyl ethyl ketone Nitriles such as niacetonitrile; N.

Examples include N,N-dialkylamides such as N-dimethylformamide and N,N-dimethylformamide, and dimethylsulfoxide.

The order of addition of the raw materials in the reaction is not particularly limited, but generally the solvent is added with the general formula (III
) is preferably dissolved in a reactor and chloroacetyl halide dissolved in a solvent is added under stirring. 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 for the reaction can be selected from a wide range, and generally varies from 0°C to 150°C, preferably from 5 minutes to 10 days, preferably from 1 to 40 hours. Further, during the reaction, it is preferable to perform stirring.

The method for isolating and purifying the target product, ie, the N-substituted chloroacetanilide represented by the general formula (I), from the reaction system is particularly special! .

Any known method can be used without being limited to. 1. For example, the reaction solution is cooled or naturally cooled to return it to room temperature or near room temperature, and the reaction solvent is added.

After distilling off the remaining hydrogen halide scavenger, 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 purified by chromatography or, if the product is a solid, by recrystallization from a solvent such as hexane.

Furthermore, 2- represented by the general formula (where A represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, and X represents a halogen atom)
Substituted thiophene and the general formula (where R1, R2 and R3 are the same or different hydrogen atoms or halogen atoms.

Indicates an alkyl group, an alkoxy group, and an alkylthio group. )
The N-substituted-chloroacetanilide represented by the general formula (I) can also be obtained by reacting with the chloroacetanilide represented by the formula (I).

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 general formula (1) and chloroacetyl halognide, which have already been described. conditions can be adopted.

The N-substituted-chloroacetanilide represented by the above general formula (I) is used for annual weeds such as field weeds and cypress that occur in paddy fields, as well as for grasshoppers, watermelon, and other annual weeds.
Omodaka.

It is an excellent herbicide that has a wide spectrum of herbicidal properties against perennial weeds such as Prunus japonicus and can efficiently control them without causing any chemical damage to paddy rice. In particular, it has an excellent herbicidal activity unparalleled by other herbicides, even when applied in a very small amount, against the perennial water cypress, which has become a problem in recent years.

(However, R4 is an alkyl group, X is a halogen atom, and Yl and Y2 are the same or different hydrogen atoms, halogen atoms, alkyl groups, or alkoxy groups, respectively.)

In the above general formula (I), the alkyl groups represented by R4, Yt and Y2 are not particularly limited in terms of carbon number, and any alkyl group may be used. Among these, those having 1 to 4 carbon atoms are preferred. A preferred alkyl group in the present invention is a medyl group.

Examples include ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, and t-butyl group. Furthermore, in the above general formula (If), the number of carbon atoms of the alkoxy group represented by Y, s, and Y2 is not particularly limited; Preferably. Preferred alkoxy groups in the present invention include methoxy and ethoxy groups.

n-propoxy Ji-propoxy group, n-butoxy group,
Examples include i-butoxy group and t-nibutoxy group. Furthermore, in the general formula (If), the halogen atoms represented by X, Yt, and Y2 are fluorine.

Examples include chlorine, bromine, and iodine atoms.

Among the amide derivatives represented by the above general formula (II), Y
Those in which l and Y2 are hydrogen atoms and X is a bromine atom are particularly preferably used because of their high herbicidal activity.

As the method for producing the amide derivative represented by the above general formula (II), any known production method can be employed without any restriction.

The amide derivative represented by the general formula (II) is known to exhibit a strong growth-controlling effect on paddy field weeds belonging to the Cyperaceae family, such as Cyperus japonica, Cyperus japonica, and Cyperus japonica, and in particular, it has a strong growth-controlling effect on rice field weeds belonging to the Cyperaceae family, such as Cyperus japonica, Cyperus japonica, and Cyperus japonica. Regardless of the situation, it has the property of always showing a stable herbicidal effect.

The herbicidal composition of the present invention exhibits excellent herbicidal effects in a wide range of usage ratios of the N-substituted chloroacetanilide represented by the general formula (I) and the amide derivative represented by the general formula (II). It will be done. However, the ratio of the amide derivative to 1 part by weight of the N-substituted chloroacetanilide is generally in the range of 0.01 to 50 parts by weight. More preferably, N-
By adding 1 to 20 parts by weight of the amide derivative to 1 part by weight of the substituted chloroacetanilide, the herbicidal effect becomes even more excellent.

When the herbicide composition of the present invention is used for paddy rice seedlings simultaneously sown in paddy soil, 1
When treated at a concentration of 0.1 g per area, germination of wild plants is completely inhibited, but paddy rice is not affected at all even when treated with 100 g. Therefore, generally 0.15 per are
It may be used in paddy fields in an amount of active ingredient of ~200(), preferably 0.5-50Q.

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 can be applied not only to rice fields, but also to various grains, legumes, and cotton.

Vegetable fields, orchards, lawns, pastures.

It is widely useful in tea gardens, mulberry gardens, forest land, non-agricultural land, 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, powders, coarse powders, and fine granules.

Powders, wettable powders, emulsions, flowable preparations.

It can be prepared and used as an oil suspension.

When preparing the herbicidal composition of the present invention into a formulation, any conventionally known solid carrier may 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, or zicrite; talc, mica, oxalite, pumice, vermiculite,
Gypsum, calcium carbonate.

Dolomite 1. Diatomaceous earth magnesium.

Inorganic substances such as lime, apatite, zeolite, anhydrous silicic acid 1 synthetic calcium silicate, etc.: soybean flour, tobacco flour, walnut flour, wheat flour.

Plant-friendly organic substances such as wood flour, starch, and crystalline cellulose:
Synthetic or natural polymer compounds such as coumaron resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, and dammar gum; Waxes such as carnauba wax and beeswax, or urea, etc. It will be done.

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. Paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene; carbon tetrachloride, chloroform, trichloroethylene, monochlorobenzene, Chlorinated hydrocarbon didioxane such as 0-chlorotoluene, ethers such as tetrahydrofuran; acetone, methyl ethyl ketone, diisobutyl ketone.

Ketones such as cyclohexanone, acetophenone, and isophorone: ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate.

Esters of diethylene glycol acetate, dibutyl maleate, geltyl succinate, etc.: methanol,
Examples include alcohols such as n-hexanol, ethylene glycol, and diethylene glycol; ether alcohols such as ethylene glycol phenyl ether, diethylene glycol ethyl ether, and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethyl sulfoxide; and water.

In addition, in the preparation of the formulation in the present invention, conventionally known surfactants are used for the purposes of emulsification, dispersion, wetting, mineral expansion, binding, disintegration control, active ingredient stabilization, flowability improvement, rust prevention, etc. It can be used without any restrictions. As surfactants, nonionic,
Cationic, anionic and zwitterionic ones are used, but usually nonionic and/or anionic ones are used. Suitable nonionic surfactants include, for example, isooctylphenol, which is obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol.

Polymerization and addition of ethylene oxide to alkylphenols such as nonylphenol: isooctylphenol, polymerization and addition of ethylene oxide to alkylphenols such as nonylphenol, polymerization and addition of ethylene oxide to alkylnaphthols such as nibylnaphthol and octylnaphthol: valmitic acid, Products obtained by polymerizing and adding ethylene oxide to higher fatty acids such as stearic acid and oleic acid: Products obtained by polymerizing and adding ethylene oxide to mono- or dialkyl phosphoric acids such as stearyl phosphoric acid and dilauryl phosphoric acid; To amines such as dodecylamine and stearic acid amide Higher fatty acid esters of polyhydric alcohols such as sorbitan and those obtained by polymerizing and adding ethylene oxide; polyhydric fatty acids such as didioctyl succinate and alcohols obtained by polymerizing and adding ethylene oxide and propylene oxide. Examples include esters of 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. : Sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate.

Examples include arylsulfonates such as sodium dodecylbenzenesulfonate, and phosphates such as sodium nitriplyphosphate.

Furthermore, in the formulation of the present invention, conventional Known adjuvants may be used without any restriction.

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, sodium alginate,
Carboxymethylcellulose, methylcellulose, hydroxyethylcellulose.

Examples include polymer compounds such as 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.

5 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 mixed together. After adding and stirring well,
There is a method of obtaining granules by extruding to a predetermined particle size and drying.

The herbicidal composition of the present invention described above exhibits a herbicidal effect that cannot be predicted from the properties of each component alone. That is,
Has a wide 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)-chenylmethyl)-
2,6-dimethylaniline 1.81g (6,14x 1
0-3 mole) was dissolved in 40 m of benzene, and 0.81 g of triethylamine (7,98 x 10°3 mole) was dissolved in 40 m of benzene.
) and placed in ice water. Then chloroacetyl chloride 0,83a (7,37x 10-3 mo, I
15 ml of the benzene solution of e) was gradually added.3
After stirring for an hour, the mixture was heated at 50° C. for 1 hour. After cooling the reaction mixture to room temperature, 50 ml of water, 50 ml of 2N-hydrochloric acid
1. Subsequently, the benzene layer was washed with 50 ml of water and dried over anhydrous sodium sulfate.

After that, it was purified by column chromatography, and 1.13g of yellow solid was obtained.
I got it. As a result of measuring the infrared spectrum of this substance, 3
Absorption based on the C-1-1 bond was observed at 110-2900aR゛1, and strong absorption based on the carbonyl bond of the amide group was observed at 1670(:l11-1).The elemental analysis value was C4
8,43%, l-14,05%, N 3.99%, (C,, H6N5OBr”Cj! < 37
0 48.20%, which is the calculated value for 2.71).
It was in good agreement with l-14, 32% and N 3.75%.

In addition, when the mass spectrum was measured, l/e37
1 shows the molecular ion peak corresponding to the molecular weight.

M', peak corresponding to Me-(, /Ic) at /e336.

The peak corresponding to Me COCHZ (,j') is shown at m/e293, and the peak corresponding to m/e143 (100%) is shown.

Furthermore, the 1H-nuclear magnetic resonance spectrum 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)-chenylmethyl)-N-chloroaceto-2,6
-Simethylanilide (hereinafter abbreviated as compound (1))
It became clear that. The yield is N-(2'-(5
49.5% (3,04x104 mol
e).

(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 formula % Formula % in Table 1 represents the general formula (I) Next, the formulation layer 1 and Examples of the herbicide composition of the present invention are shown. In addition, in the blended layer and examples, up acetanilide by replacing N- is the compound number [(1) to (52) in the synthesis side.
, ), and the 7mido derivative is represented by the following symbol ([A]
It is expressed as ~ [engineering]).

Below is a blank formulation example 1: 100 parts by weight of compound (A), 1 part by weight of compound (1), 1.5 parts by weight of surfactant Tsurupol 800A (trademark of Toho Chemical Industry Co., Ltd.), and 1.5 parts by weight of surfactant Detergent 60 (Lion Yushi Co., Ltd.) ) 31.5 parts by weight of the trademark and 86 parts by weight of Zikrite 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),
Surfactant Tsurupol 5M100 (Toho Chemical Industry Co., Ltd.)
315 parts by weight of the trademark 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.
Parts by weight were thoroughly mixed and pulverized, water was added, kneaded, granulated and dried, and sized to 14 to 32 meshes to obtain granules.

40 parts by weight of bentonite, 55 parts by weight of talc, and 5 parts by weight of sodium tripolyphosphate are pulverized and mixed, added with water, mixed, and then granulated and dried to produce granules containing no active ingredient. 10 parts by weight of compound (A) and 5 parts by weight of compound (30) were impregnated into 855 parts by weight of the granules to obtain granules.

Example 1 A Wagner pot equivalent to 1/5000 are is filled with watered and kneaded paddy soil, and the surface layer of the soil is planted with wild grasses, cypresses, bulrushes, and porcupines.

Seeds of broad-leaved weeds such as azalea and japonica were sown, and tubers of urikawa and cypress were embedded.

In addition, 2c of rice seedlings (variety name: Akinishiki) at the 2.5M stage
Three plants were planted at the depth of the IR. Thereafter, the rice was grown in a glass room at 20 to 25°C under water conditions of about 3 cm, and 7 days after transplanting the rice (when the wild plants were at about 0.8 leaf stage) and 14 days after (when the wild plants were at about 2 leaf stage). According to Formulation Example 1,
The prepared wettable powder was diluted with water and a predetermined amount was dropped. Thereafter, they were grown in a glass room, and on the 21st day after the chemical treatment, the herbicidal effect and the chemical damage to paddy rice were investigated. The result is the second
Shown in the table.

Weeding effect Paddy rice chemical damage suppression rate (%) -: Normal" 5: 100 (complete withering) ±: Slight damage 4: 15-9
9+: Minor damage 3: 50-74 -1-1-: Nakayori 2: 25-49 1: 1-24. 0:0 (no effect observed at all) Below margin

[Brief explanation of drawings]

FIG. 1 shows a chart of 11-1-1-N of N-substituted-chloroacetanilide obtained in Synthesis Example 1. Patent applicant Tokuyama Sotatsu Co., Ltd.

Claims (1)

[Scope of Claims] The following formula (wherein A is a hydrogen atom, a halogen atom, represents an alkyl group, an alkoxy group, or an alkylthio group, and R+, R2, and R3 are the same or different hydrogen atoms, halogen atoms, Alkyl group, alkoxy group,
Indicates an alkylthio group. ) (wherein, R4 is an alkyl group, X is a halogen atom, and Ys and Y2 are each the same or different hydrogen atom, halogen atom, alkyl group, or alkoxy group) 1. A herbicide composition comprising an amide derivative as an active ingredient.