JPS61145101A - Herbicide composition - Google Patents

Abstract

PURPOSE:The titled composition having stable herbicidal effects with a small amount of it, suable in a wide range such as paddy fields, plowed fields for beans, orchards, etc., showing effects by treatment before and after germination, obtained by adding a specifid amount of white carbon to an N-substituted chloroacetanilide. CONSTITUTION:An N-substituted chloroacetanilide shown by the formula I (R1, R2 and R3 are H, halogen, alkyl, alkoxy, etc.; R4 is H, or alkyl; R5, R6, and R7 are H, halogen, alkyl, alkenyl, alkynyl, etc.) is blended with 15-400 times, preferably 30-200 times as much white carbon by weight. When it is used, it is preferably used as granular. The white carbon is a general term for silica white filler including artificially produced ultrafine silicic acid or silicate. The active ingredient compound shown by the formula I is obtained by reacting an aniline derivative shown by the formula II with a compound shown by the formula III (X is halogen).

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a herbicidal composition characterized by mixing N-substituted chloroacetanilide with white carbon (hereinafter abbreviated as whiker).

[Problem 3 to be solved by the prior art and the invention There are the following four properties that are essentially required of the herbicidal preparation. That is, one, it must be safe for crops, and two, it must be safe for crops.
Firstly, it should exhibit an even and stable weeding effect against weeds. The third is that the herbicide's effectiveness lasts for a long time;
Fourthly, due to environmental issues, cost, etc., it is necessary to have a more effective herbicidal action with a lower content of active ingredients.

The present inventors have conducted extensive research with the aim of developing a formulation represented by the following general formula as an excellent herbicide.

The following general formula (1), R5 (wherein R+, Rz and R3 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups or alkylthioalkyl groups, and R1 represents a hydrogen atom or an alkyl group, Rs, Rh and R1 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups,
An N-1t-substituted chloroacetanilide represented by ), which represents an alkoxy group or an alkylthio group, has already been proposed (Japanese Patent Application No. 111077/1983 and others). Naturally, the role of formulations in the expression of herbicide effects is very important.

That is, it is almost impossible to expect a sufficient herbicidal effect unless the physical or chemical properties of the drug substance are carefully considered and the optimal formulation is formulated.

The present inventors have discovered that the N-substituted-
With the aim of using chloroacetanilide more effectively as a herbicide, we have continued intensive research on its formulation, and have found that N
- The herbicidal composition obtained by mixing Horica with substituted chloroacetanilide exhibits a synergistic effect that could not be expected from the properties of each alone, that is, stable herbicidal effects at low dosages. I discovered something. Based on these new findings, the present inventors have completed and proposed the present invention.

[Means for solving problems]

The present invention is based on the following general formula (I), Rs (where Rt, Rt and R3 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups or alkylthioalkyl groups). R1 represents a hydrogen atom or an alkyl group, R5, R.

and R9 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, or alkylthio groups. This is a herbicide composition characterized by mixing an N-substituted chloroacetanilide represented by the following formula and a herbicide.

In the present invention, Holica is a general term for white silica fillers containing artificially produced fine particles of silicic acid and silicate.

The component of the herbicidal composition of the present invention is N-11-chloroacetanilide represented by the following general formula (11).

In the N-substituted-chloroacetanilide represented by the above general formula CI), the 2-position of the thiophene ring and -CH- are bonded, R, is a hydrogen atom or an alkyl group, Rt, R
Compounds in which a and R4 are hydrogen atoms, Rs is an alkyl group, R6 is a hydrogen atom, an alkyl group, or an alkoxy group, and R1 is a hydrogen atom, an alkyl group, or a halogen atom are disclosed in US Pat. No. 3,901,917. It is publicly known. However, most of the others are new compounds.

In the general formula CI), specific examples of the halogen atoms represented by R3, R2, R3, R1, R, and R1 include chlorine, bromine, fluorine, and iodine atoms. Also,
In the general formula, R,, Rz, Rs, Ra, Rs,
The alkyl groups represented by R6 and R1 may be linear or branched, and the number of carbon atoms is not particularly limited.

However, from the viewpoint of easy availability of raw materials, the number of carbon atoms is preferably 1 to 6. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, 1so-propyl group, n-butyl group, 1so-butyl group, 1-butyl group, n-pentyl group, n-hexyl group. etc.

In the general formula [T), the alkoxy groups represented by R, R2, R3, R3, R6 and R1 are not particularly limited, but
In general, linear or branched saturated or unsaturated groups having 1 to 6 carbon atoms are preferred. Specific examples of the alkoxy group that are generally preferably used include methoxy group, ethoxy group, n-propoxy group, t-butoxy group, n
-pentoxy group, n-hexoxy group, allyloxy group and the like.

In the general formula [■], RI, Rz, R3, Rs, R
The alkylthio group represented by 6 and R7 is not particularly limited and any known alkylthio group can be used, but -i has 1 to 1 carbon atoms.
Six linear 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,
Examples include n-hexylthio group and allylthio group. Further, in the above general formula, the alkoxyalkyl group represented by R+, Rz and R1 is not particularly limited in the number of carbon atoms, but a linear or branched saturated or unsaturated group having 2 to 6 carbon atoms is preferable. Specific examples of the alkoxyalkyl group include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an n-propoxymethyl group, a t-butoxyethyl group, an allyloxyethyl group, and the like. Furthermore, in the general formula, the alkylthioalkyl groups represented by RI, Rz and R1 are not particularly limited in number of carbon atoms, but are preferably linear or branched saturated or unsaturated groups having 2 to 6 carbon atoms. Specific examples of the alkylthioalkyl group include methylthiomethyl group, methylthioethyl group, ethylthiomethyl group, n-propylthiomethyl group, t-butylthioethyl group, and allylthioethyl group.

In addition, in the general formula, the alkenyl group represented by R, R, and R7 may be linear or branched,
- Eagle (the number of carbon atoms is not particularly limited, but from the viewpoint of easy availability of raw materials, the number of carbon atoms is preferably 2 to 4. Specific examples of the alkenyl group include vinyl group, allyl group, 1so -propenyl group, 2-butenyl group, 3-
Examples include butenyl group. Furthermore, in the general formula, R5
, R4 and R6, regardless of whether they are linear or branched, and the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms is 2 to 4 as described above. Specific examples of the alkynyl group include ethynyl group, 2-propynyl group, and the like.

Among the above N-substituted-chloroacetanilides, R3 is the same or different halogen atom, alkoxy group, alkylthio group, alkoxyalkyl group, or alkylthio group,
an alkoxyalkyl group or an alkylthioalkyl group, in which R2 and R3 are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups,
an alkoxyalkyl group or an alkylthioalkyl group, R4 is a hydrogen atom or an alkyl group, R6, R
1 and R7 are the same or different hydrogen atoms, halogen atoms,
Compounds that are alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups or alkylthio groups: 15g/10a
Even when used at lower concentrations, it not only has an excellent herbicidal effect that can completely kill annual weeds such as field weeds and perennial weeds such as water cypress.
Since it is completely harmless to rice even when used at a high concentration of 500 g/10a, it is suitably used in the present invention. In particular, at least one of RI-Rs is a substituent other than a hydrogen atom, and this substituent is substituted at the ortho position of one CH- bonded to the 1,000-offene ring, and R4 is a hydrogen atom. , Furthermore, at least two of R2-R1 are substituents other than hydrogen atoms, and N-substituted-chloroacetanilide in which these substituents are substituted at the 2- and 6-positions of the phenyl group has stronger the above properties. , is particularly preferably used.

The structure of the N-W substituted chloroacetanilide represented by the general formula (1) can be confirmed by the following means.

(b) By measuring the infrared absorption spectrum (rR), it is possible to observe the absorption based on the CH bond in the vicinity of 3150 to 2800 cm+-' and the carbonyl bond of the amide group in the vicinity of 1680 to 1660 cm-' (observing the characteristic absorption I can do it.

(b) 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. In other words, when a sample subjected to measurement is expressed by the general formula (1), the molecular ion peak ■ (hereinafter abbreviated as M) generally varies in intensity according to the isotope abundance ratio depending on the number of halogen atoms contained in the molecule. Since it is observed as a ratio, it is possible to determine the molecular weight of the compound subjected to measurement. Furthermore, it is represented by the general formula CI) and
A characteristic strong peak corresponding to R+ is observed, and the binding mode of the molecule can be known.

(c) lH-nuclear magnetic resonance spectrum ('H-NMR
), it is possible to know the bonding mode of hydrogen atoms present in the N-substituted-chloroacetanilide represented by the general formula (1). 'H-NM of N-substituted-chloroacetanilide represented by the general formula (1)
As a specific example of R (δ, 1) pH: based on tetramethylsilane, in deuterated chloroform solvent), N-[2”-(5”
-bromo)-thenylmethyl)-N-chloroacetyl)-2
, 6-dimethylanilide.
The analysis results shown in the figure are as follows.

H(a) H(bl CHs (d)
H(e) i.e. 6 protons at 2.0 ppm
A singlet corresponding to two protons was observed, and this can be attributed to the methyl group (dl) substituted at the 2 and 6 positions of the phenyl group.A singlet corresponding to two protons was observed at 3-6pl'lll. This can be attributed to the methylene group 1hl in the chloroacetyl group.4.75ppT
A singlet corresponding to two protons was observed at @, and this can be attributed to the methylene group (C). 6.67
A quartet corresponding to two protons is observed in pp-,
This can be attributed to the thiophene ring di[111 proton (a), mountain). 6.95-7.30ppm
A multiplet corresponding to three protons was observed in
It can be attributed to

Summarizing the IH-NMR characteristics of the N-substituted chloroacetanilide represented by the general formula (1) above, the methylene proton of the chloroacetyl group is normally 3.6 to 3.6 to
It appears around 3,8 pp+s, and when R4 is a hydrogen atom, the methylene proton of the aminomethylene group is a singlet around 4.7 to 5.099 ta (however, the 2.6 position on the aniline side is asymmetrically If a substituent exists, it may appear as a double line), and when R4 is an alkyl group, the methine proton of the aminomethine group is 5.7
~6.7 ppm, and the proton of the thiophene ring example is 5.5 ppm.
8 to 7.4 ppm, and the proton on the benzene side is 6.0
It tends to show a characteristic peak at ~7.799rs.

(d) The weight percent of oxygen can be calculated by determining the weight percent 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. Therefore, the compositional formula can be determined.

Further, N-substituted-chloroacetanilide is Rr, Rt, Rs, Ra, Rs, Ra in the general formula (1).
and R? Although its properties differ somewhat depending on the type, it is generally a pale yellow or yellow viscous liquid or solid at room temperature and normal pressure, and many have an extremely high boiling point.Specifically, as shown in the synthesis examples below, As with general organic compounds, the boiling point of the above compound tends to increase as the molecular weight increases. 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 [1] is not particularly limited. A typical production method is described below. General formula (wherein R, , R, and R1 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, or alkylthioalkyl groups, and R4 represents a hydrogen atom or
・−.

represents an alkyl group, and Rs, Ri, and R7 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, or alkylthio groups) and an aniline derivative represented by the general formula Cl1cHz
By reacting with chloroacetyl halide represented by cox (wherein, X represents a halogen atom), the N-substituted-chloroacetanilide represented by the general formula (I) can be obtained.

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 CI) and chloroacetyl halide, the molar ratio of the compound to be added may be appropriately determined as necessary, but it is usually the same molar amount 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 aniline derivative represented by the general formula (III) in the reaction system and causes a decrease in the yield of the product, a hydrogen halide scavenger is usually coexisted in the reaction system. The hydrogen halide scavenger, which is preferred, 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.

In the reaction, it is generally preferable to use an organic solvent. Examples of suitable solvents include:
Benzene, toluene, xylene, hexane, heptane,
Aliphatic or aromatic hydrocarbons or halogenated hydrocarbons such as petroleum ether, chloroform, methylene chloride, and ethylene chloride; Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Acetonitrile, etc. Nitriles; N,N-dialkylamides such as N,N-dimethylformamide and N,N-diethylformamide; dimethylsulfoxide and the like.

The order of addition of raw materials in the reaction is not particularly limited, but generally, the aniline derivative represented by the general formula [111] is dissolved in a solvent, the mixture is charged into a reactor, and the chloroacetyl halide dissolved in the solvent is added under stirring. It is better.

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 above reaction can be selected from a wide range, and generally it is sufficient to select it from the range of -20°C to 150°C, preferably 0°C to 120°C. The reaction time varies depending on the type of raw material, but is usually 5 minutes to 10 days, preferably 1 to 40 days.
It is sufficient to choose from the time range. It is also preferable to stir the reaction mixture during the reaction.

The method for isolating and purifying the desired product, ie, the N-substituted-chloroacetanilide represented by the general formula CI) 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 purified by chromatography, or if the product is a solid, by recrystallization from a solvent such as hexane.

As another method for producing the N-substituted-chloroacetanilide represented by the general formula (1), the following method is also preferably employed.

General formula (wherein R+, Rz and R1 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, alkylthioalkyl groups, and R4 represents a hydrogen atom or an alkyl group) and X represents a halogen atom. basis,
The N-substituted chloroacetanilide represented by the general formula (T) can also be obtained by reacting with chloroacetanilide represented by ), which represents an alkoxy group or an alkylthio group.

The substituted thiophene and the chloroacetanilide used as raw materials can be obtained by any method.

In addition, the conditions and isolation and purification method used to carry out this reaction are almost the same as those used in the reaction of the aniline derivative represented by the general formula Cl11) with chloroacetyl halide as described above. conditions can be adopted.

The N-substituted-chloroacetanilide represented by the above general formula (1) has a wide herbicidal spectrum against annual weeds such as field weeds and grasshoppers that occur in rice fields, as well as perennial weeds such as fireflies and snails, It is also an excellent herbicide that can efficiently control paddy rice without causing chemical damage.

The other component of the herbicidal composition of the present invention is a herbicide. There are no particular limitations on the Holaika species, and known ones can be used as they are.
Used.

For example, artificially produced silicic acid and silicate as shown in "Practical Handbook of Additives for Plastics and Rubber" published by Kagaku Kogyo Co., Ltd. (published August 10, 1970), pages 541 to 560 are suitable. Can be used. Particularly suitable are hydrated silicic acid produced by a wet method, and whica called anhydrous silicic acid produced by a dry method. Among silicates, fine powder calcium silicate is preferred. These squids may be used simply or in a mixture of different types.

As mentioned above, the herbicidal composition of the present invention has the general formula (I)
It consists of a mixture containing an N-substituted chloroacetanilide represented by In herbicide compositions containing Z-substituted chloroacetanilides, N-substituted chloroacetanilides and Horicas can provide excellent herbicidal effects in extremely wide ranges of usage ratios. However, it is generally preferable to select the amount of holica to be used in a range of 15 to 400 times, preferably 30 to 200 times, the weight of the N-substituted-chloroacetanilide.

Some of the herbicide compositions of the present invention are effective when used in the form of granules, but the method for producing the granules is not particularly limited, and any known method can be used as is. For example, in addition to the above-mentioned N-substituted chloroacetanilide and Holica, adjuvants used for improving properties such as surfactants, carriers, and disintegration properties, which are commonly used in granules.
In general, polymer compounds such as casein, gelatin, glue, cellulose, etc. can be appropriately selected and used as long as the effects of the present invention are not impaired.

For example, the following method can be suitably employed. That is, N
-Knead 1 part by weight of substituted chloroacetanilide, a surfactant, and water, then add a carrier containing starch and a surfactant, stir well, extrude to a predetermined particle size, and dry. There is a method of obtaining granules by

The carrier may be appropriately selected from known carriers, but examples of carriers that are generally preferably used include, for example, kaolinite group,
Clay aggregates represented by montmorillonite group, attapulgite group, gicrite, etc. talc, mica, phyllite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth magnesium, lime, apatite, zeolite, anhydrous silica Inorganic substances such as acids and synthetic calcium silicate; Vegetable organic substances such as soybean flour, tobacco powder, walnut flour, wheat flour, wood flour, and crystalline cellulose; Coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol Examples include synthetic or natural polymeric compounds such as , ketone resin, ester gum, copal gum, and dammar gum; solid carriers of waxes such as carnauba wax and beeswax, and urea.

Liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, and white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, and methylnaphthalene; carbon tetrachloride, and chloroform. , trichlorethylene, monochlorobenzene, 0-chlorotoluene; ethers such as dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate, Ethylene glycol acetate, diethylene glycol acetate,
Esters such as diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, n-
Examples include alcohols such as 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.

Furthermore, as the surfactant, nonionic, cationic, anionic, and amphoteric surfactants are used, but nonionic and/or anionic surfactants are usually preferably used. . Suitable nonionic surfactants include:
For example, ethylene oxide is polymerized and added to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol; ethylene oxide is polymerized and added to alkyl phenols such as isooctylphenol and nonylphenol; ethylene oxide is polymerized and added to alkylphenols such as isooctylphenol and nonylphenol. Added Nibutylnaphthol,
Ethylene oxide is polymerized and added to alkylnaphthols such as octylnaphthol; ethylene oxide is polymerized and added to higher fatty acids such as balmitic acid, stearic acid, and oleic acid; stearyl phosphoric acid (dilauryl phosphoric acid can also be converted to mono- or dialkyl phosphoric acid) Polymerized addition of ethylene oxide to amines such as dodecylamine and stearic acid amide; Higher fats of polyhydric alcohols such as sorbitan
Examples include esters and those obtained by polymerizing and adding ethylene oxide to them; esters of polyhydric fatty acids and alcohols such as nidioctyl succinate, which is obtained by polymerizing and adding ethylene oxide and propylene oxide.

a Suitable anionic surfactants include, for example, alkyl sulfate ester salts such as sodium lauryl sulfate and oleyl alcohol sulfate amine salt; alkyl sulfonic acids such as sodium sulfosuccinate dioctyl ester and sodium 2-ethylhexene sulfonate; Salts: Aryl sulfonates such as sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, sodium dodecylbenzenesulfonate; phosphates such as sodium tripolyphosphate; and the like.

(Actions and Effects) The herbicidal composition of the present invention exhibits significantly more stable medicinal efficacy than those that do not contain any N-terminus or have a small amount of N-
Replacement - Even if the content of chloroacetanilide is reduced, the same or higher herbicidal effect will be achieved. However, it is still not clear what kind of mechanism of action produces these effects. Granules containing Tazohoika have a lower disintegration and spreadability in water compared to granules that do not contain Tazohowaika. Considering the negative phenomena, it is presumed that this difference in disintegration spreadability has some influence on the biological effect.

The herbicide composition of the present invention is effective even when treated before and after weed germination, and is also highly effective in soil treatment and foliage treatment. It is useful in a wide range of areas including rice fields, fields of various grains, pulses, cotton, vegetable crops, orchards, lawns, old grasslands, tea gardens, mulberry gardens, forests, non-agricultural lands, etc. .

Furthermore, 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.

N--chloroacetanilide person (synthesis example 1) N-[2°-(5''-bromo)-thenylmethyl)-
2,6-dimethylaniline 1,81 g (6,14X
10-'+5ole) in 40ml of benzene and 0.81 g of triethylamine (7,98
mole) and placed in ice water. Then 0.83 g of chloroacetyl chloride (7,37X 10-'
A benzene solution (15 mJ) of mol) 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, 5 Qml of water, 5 Qml of 2N-hydrochloric acid
0m7! Then, the benzene layer was washed with 5 Qml of water and 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 absorption spectrum of this material, 3110
Absorption based on C-H bond at ~2900 cm-', 167
A strong absorption based on the carbonyl bond of the amide group was observed at 0c+w-'. Its elemental analysis value is C48, 43%, H4
,05%, N3.99%, C+sl(+5NS
OBr Cj! The calculated values for (372,71) were C 48.20%, H4 32%, and N 3.75%.

In addition, when the mass spectrum was measured, ■ M -CHCH! Peak corresponding to C1, m/e1
Each peak corresponding to 43 (100%) is shown.

Furthermore, the 'H-nuclear magnetic resonance vector 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)-thenylmethyl-
-Simethylanilide (hereinafter abbreviated as compound (1))
It became clear that. The yield is N-[2゜-(5
°-bromo)-thenylmethyl]-2,6-dimethylaniline, 49.5% (3,04%
ole).

(Synthesis Example 2) The properties, physical properties (boiling point), characteristic absorption values in the infrared spectrum, and elemental analysis results of N-substituted-chloroacetanilide synthesized in the same manner as in Synthesis Example 1 are summarized in Table 1.

In addition, single-vessel type in Table 1 is the general formula [1] means.

Formulation Example 1 1 part by weight of the compound No. 39 in Table 1, 50 parts by weight of Tokusil P (trade name of white carbon obtained by a wet method, manufactured by Tokuyama Soda), 4 parts by weight of dioctyl succinate, 4 parts by weight of sodium tripolyphosphate Part by weight, bentonite 25
Parts by weight and 16 parts by weight of talc were thoroughly mixed and pulverized, water was added and kneaded, and the mixture was granulated and dried, and the particles were sized to 14 to 32 mesh sizes to obtain granules.

Formulation Example 2 Fluorite R (Tokuyama Soda Specialty, trade name of calcium silicate) 30 parts by weight, bentonite 15 parts by weight, talc 50 parts by weight
Parts by weight and 5 parts by weight of sodium tripolyphosphate were pulverized and mixed, added with water, kneaded, and then granulated and dried to obtain granules. To 99 parts by weight of this granule, 1 part of the compound N140 of Table 1 was added.
It was impregnated with part by weight to form granules.

Formulation Example 3 5 parts by weight of the compound listed in Compound 50 in Table 1, 60 parts by weight of Carbrex #80 (manufactured by Shionogi & Co., Ltd., trade name of White Carbon), 3 parts by weight of sodium lignin sulfonate, 1 part by weight of dioctyl succinate. , 20 parts by weight of bentonite, and 11 parts by weight of talc were thoroughly mixed and pulverized, water was added and kneaded, and the mixture was granulated and dried, and the particles were sized to 14 to 32 mesh sizes to obtain granules.

Comparative Formulation Example For those containing no white carbons, granules were obtained in the same manner as in Formulation Example 1.2.3 using various clay minerals instead of white carbons.

<Example> A Wagnerbot with an area equivalent to 1/8850 are was filled with paddy soil that had been mixed with water, and wild grass seeds were sown on the surface layer of the soil, submerged in water to a depth of approximately 3 cm, and placed in a glass room at 20 to 25°C. After 14 days (when the wildflowers are at the two-leaf stage), a predetermined amount (3 kg/10
a) Treated. Thereafter, the plants were grown in a glass room, and the herbicidal effect was investigated on the 21st day after the chemical treatment. The results are shown in Table 2.

In addition, the compound group in Table 2 indicates the compound magnetic compound confirmed in Table 1. In addition, the herbicidal effect was evaluated using the following 6-level method.

Weeding effect Weed suppression rate (%) 5:100 (completely dead) 4 near 5~99 3:50-74 2:25-49 1: 1-24 0: 0 (No effect observed at all.) (Table 2)

[Brief explanation of drawings]

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

Claims (1)

[Claims] The following general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ Represents an alkyl group or an alkylthioalkyl group, R_4 represents a hydrogen atom or an alkyl group, and R_5, R_6, and R_7 represent the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, or alkylthio A herbicidal composition characterized in that white carbon is mixed 15 to 400 times by weight N-substituted-chloroacetanilide represented by the following formula.