JPS6365064B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel N-substituted-chloroacetanilide having a specific general formula and a process for producing the same. The present invention also provides a herbicide containing the above compound as an active ingredient. Conventionally, several kinds of compounds of N-substituted-chloroacetanilide are known. Some species are also known to be effective as herbicides.
For example, in Special Publication No. 55-34122, the general formula (However, R ₁ and R ₂ are alkyl groups such as methyl group and ethyl group) N-substituted chloroacetanilide has been shown to have activity as a herbicide. However, the N-substituted-
The selective herbicidal activity of chloroacetanilide is small;
For example, at a concentration of 125 g/10a, it already causes phytotoxicity to rice, and has the disadvantage that it does not exhibit herbicidal activity against wild grass unless the concentration exceeds that concentration. On the other hand, conventionally commercially available herbicides have the disadvantage that they are extremely difficult to apply to flooded, directly sown paddy rice or young seedlings immediately after transplantation. In addition, in order to increase herbicide efficiency, it is common to use extremely high concentrations, for example, 100g/10a or higher, and the use of such high concentrations is not only economical, but also prevents herbicides from flowing into river water, making them less useful. There are also disadvantages that affect aquatic animals. Therefore, it has been desired to develop a new compound that has a herbicidal effect even when used at a low concentration and at the same time has a selective herbicidal activity that kills only weeds. The present inventors have conducted extensive research in order to develop new compounds that meet the above requirements. As a result, we succeeded in synthesizing an excellent new compound that compensates for the various drawbacks mentioned above, and have come to propose it here. That is, the present invention provides the general formula,

[Formula] (However, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, and R ₃
and R ₄ each represent the same or different hydrogen atom or methyl group, and Y represents a hydrogen atom or a chlorine atom. ) is provided. Further, the present invention relates to the general formula,

[Formula] N-halomethyl-chloroacetanilide and general formula,

【formula】 By reacting the alcohol represented by the general formula,

A method for preparing an N-substituted chloroacetanilide of the formula is also provided. However, in the above formula, X represents a halogen atom, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, and R ₃ and R ₄ represent the same or different hydrogen atom or methyl group, respectively. and Y represents a hydrogen atom or a chlorine atom. Furthermore, the present invention provides the general formula,

[Formula] (However, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, R ₃ and R ₄ each represent the same or different hydrogen atom or methyl group, and Y is a hydrogen atom. or a chlorine atom) as an active ingredient. The N-substituted-chloroacetanilide provided by the present invention has the general formula: (However, R ₁ , R ₂ , R ₃ , R ₄ and Y are the same as shown in the general formula above.)
The compound represented by the above general formula () is a novel compound. In addition, as is clear from the examples described later, this compound can be used at a high concentration, for example, 1000g/
Not only is it completely non-toxic and safe to rice even when used at 10a, but it also has an extremely significant selective herbicidal activity that completely kills weeds such as wild grass even when used at a low concentration of 31g/10a or lower. . Such remarkable selective herbicidal activity is evident from the comparison with the comparative example described below, as is evident from the comparison with the comparative example described below.
This effect is mainly brought about by the chlorine atom introduced into the cyclopropane ring, regardless of the type of alkyl group at the 6-position. The compound represented by the general formula () is a novel compound. The structure of the compound represented by the general formula () can be confirmed by the following method. (a) Measurement of infrared absorption spectrum (IR). When measuring the IR of the compound represented by the general formula (), the aromatic ^ring carbon -
Absorption based on hydrogen bonds, absorption based on aliphatic carbon-hydrogen bonds around 3000-2850 cm ^-1 , 1690-
Strong absorption based on the carbon-oxygen double bond of the amide compound near 1650 cm ^-1 , absorption based on the carbon-oxygen bond of the ether bond near 1110 to 1050 cm ^-1 , and absorption based on the carbon-chlorine bond near 830 to 730 cm ^-1 Absorption appears respectively. (b) ¹³ carbon nuclear magnetic resonance spectrum ( ¹³ C−
NMR) measurement. ¹³ C− of the compound represented by the general formula ()
By measuring NMR, the following is revealed. A peak of methylene group of N-CH ₂ -O- appears around 80 ppm. A carbonyl carbon peak appears around 168 ppm. The methyl carbon peak of the chloromethyl group appears around 42 ppm. 3 forms an aromatic ring around 90-170ppm
Peaks of class carbon and quaternary carbon appear. By comparing the relative intensity ratio of each peak under quantitative measurement conditions, the number of different or similar bonding groups can be determined. Considering the results of IR measurement, mass spectrum measurement and elemental analysis described later, ^13C -NMR assignment is performed using the Savitsky rule. (R ₁ and R ₂ in the above general formula ())
It can be seen that they are connected. (c) Measurement of mass spectrum (Mass). Measure the mass of the compound represented by the general formula () and calculate the composition formula corresponding to each observed peak (generally the mass number expressed as m/e, which is the ion molecular weight divided by the ion charge number e) By doing so, the molecular weight and binding mode of the compound can be estimated. That is, in the mass measurement of the compound represented by the general formula (), the molecular ion peak (hereinafter abbreviated as M) appears with an intensity ratio according to the isotope abundance ratio depending on the number of chlorine. You can know the number of chlorine atoms. Furthermore, a split ion peak corresponding to the compositional formula in which the substituted cyclopropylmethoxy group is removed from M 2 and a split ion peak corresponding to the chloroacetyl ion can also be observed. (d) Elemental analysis By conducting elemental analysis of the compound represented by the general formula (), the weight percentages of carbon, hydrogen, nitrogen, and chlorine can be determined. The amount of oxygen can be calculated by subtracting the sum of the four elements mentioned above from 100. The compositional formula can be determined from the above results. Also, N-substituted- represented by the general formula ()
Chloroacetanilide is a colorless liquid or white solid. However, if the purification in the manufacturing process is insufficient, it may turn yellowish brown in color. Further, the compound is almost insoluble in water, but easily soluble in organic solvents such as chloroform, ether, methanol, ethanol, benzene, hexane, N,N-dimethylformamide, and dimethyl sulfoxide. Furthermore, the compound exists stably in an organic solvent or a water-containing organic solvent even when heated to about 100°C, but may decompose when heated for a long time at a temperature of 150°C or higher. The method for producing the compound represented by the general formula () of the present invention is not particularly limited. The following is an example of a typical manufacturing method. general formula (However, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, and X represents a halogen atom.) N-halomethyl-chloroacetanilide represented by the general formula (However, R ₃ and R ₄ represent the same or different hydrogen atoms or methyl groups, respectively, and Y represents a hydrogen atom or a chlorine atom.) By reacting the alcohol represented by the above general formula (), The indicated compound is obtained. N-halomethyl- represented by the general formula ()
Since chloroacetanilide is active against water, the compounds in the reaction system, that is, the compounds represented by the above general formulas () and (), as well as solvents and additives used as necessary, should all be used in a dry state. death,
It is preferable to maintain the gas phase of the reaction system in a dry state. Further, the molar ratio of the compounds represented by the general formulas () and () may be appropriately determined and used as required, but it is common to use equimolar amounts.
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 () and/or () in the reaction system,
Since it causes a decrease in the yield of the product, it is usually preferable to coexist a hydrogen halide scavenger in the reaction system. The hydrogen halide scavenger is not particularly limited and any known one can be used. Examples of scavengers that are generally preferably used include, for example,
Trialkylamines such as trimethylamine, triethylamine, tripropylamine; pyridine;
Sodium alcoholate; sodium carbonate, etc. are preferably used. It is generally preferable to use an organic solvent in the reaction in the present invention. Examples of suitable solvents include benzene, toluene, xylene, hexane, heptane,
Aliphatic or aromatic hydrocarbons or halogenated hydrocarbons such as petroleum ether, chloroform, methylene chloride, ethylene chloride; diethyl ether,
Ethers such as dioxane and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile; N,N-
Examples include N,N-dialkylamides such as dimethylformamide and N,N-diethylformamide; dimethylsulfoxide, and polar nonaqueous solvents are particularly preferred. 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 and charged into a reactor, and the compound represented by the general formula () dissolved in the solvent is added. It is best to add it while 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 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 °C. Although the reaction time varies depending on the type of raw materials, it is usually sufficient to select from a range of 5 minutes to 10 days, preferably 1 to 40 hours. Further, it is preferable to stir the reaction system during the reaction. The method for isolating and purifying the target product, ie, the compound represented by the general formula () from the reaction system, is not particularly limited, and any known method can be employed. For example, the reaction solution is returned to room temperature or close to it by cooling or natural cooling,
After distilling off the reaction solvent and the remaining hydrogen halide scavenger, the residue is extracted with ether. With the above operation,
Salts and high molecular weight compounds produced from the by-produced hydrogen halide and the hydrogen halide scavenger are separated. The ether layer is dried with a desiccant such as Glauber's salt or calcium chloride, then the ether is distilled off, and the residue is recrystallized from hexane, for example, to obtain the desired product. Instead of the recrystallization method, purification by chromatography or both may be used in combination. Some target products exist as solids only at low temperatures, while others exist as liquids at room temperature.
Therefore, it is only necessary to select the most suitable purification means depending on the properties of the desired product. The compound represented by the general formula () of the present invention exhibits remarkable effects as a herbicide. For example, it exhibits an excellent herbicidal effect when treating grass weeds, broad-leaved weeds, and perennial weeds with soil before and after germination. In particular, it shows a remarkable herbicidal effect on grass weeds, for example, it shows an excellent herbicidal effect not only on the harmful weed grass field grass when it germinates but also when it grows at the 1.5 leaf stage. Moreover, it is highly safe for paddy rice not only for young seedlings at the 1.5-leaf stage but also during germination. Since it has a highly selective herbicidal effect, it has the advantage that the suitable treatment period is significantly longer than that of conventional herbicides. Because it has the above characteristics, it can also be applied to flooded direct sowing cultivation, which simplifies the cultivation style and greatly reduces labor, and is also effective in streamlining agricultural work. In addition, when used as a herbicide in upland fields, it exhibits a selective herbicidal effect, so it can be applied not only to broad-leaved crops such as soybeans, cotton, and cornflowers, but also to gramineous crops such as wheat, barley, corn, and upland rice without causing damage. I can do it. Representative examples of specific embodiments in which the compound represented by the general formula () is used as a herbicide will be described below. When the compound represented by the above general formula () is used for wild plants and paddy rice that are sown at the same time in paddy soil, when 31 g per 10 ares is applied, the germination of wild plants is completely inhibited, but 1000 g of paddy rice is treated. In this case, it has no effect at all. Therefore, generally 6.25g to 2000g, preferably 30g to 500g per 10 ares
More preferably, it may be used in paddy fields in an amount of 100g to 250g of the active ingredient. In addition, the amount of medicine applied to the field is 12.5g to 2000g per 10 ares, preferably 200g.
A range of 1500 g to 1500 g is suitable. As mentioned above, it has selective herbicidal activity between grasshoppers and paddy rice, so it can be applied during the long-term growth stage of paddy rice from the germination period to the growth period, and it can be applied particularly safely to flooded and directly sown paddy rice. Advantages are major features of the invention. Although the compounds represented by the above general formula () of the present invention have slightly different herbicidal effects depending on their functional groups, they have little phytotoxicity against gramineous crops, and especially extremely little phytotoxicity against paddy rice. Points are common characteristics. Examples of weeds on which the compound of the present invention exhibits herbicidal effects are as follows. As mentioned above, it has a high herbicidal effect on grass family weeds, especially grasshoppers, and has a particularly favorable herbicidal effect on Cyperaceae, especially Cyperaceae, scallops, and the like. Next to these, it is preferable to use a mixture of known herbicides such as phenoxy compounds, amide compounds, etc., which have a herbicidal effect on broad-leaved weeds, but increase the amount of active ingredients used. Weeds that can be particularly effectively weeded include,
Japanese cabbage, Japanese cyperus, Japanese cypress, water lily, Japanese cyperus, Japanese cyperus, firefly, Japanese cypress, Japanese woodpecker, Japanese red violet, Hideriko, Japanese cyperus, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, silver cypress, silver lily, Japanese cypress, Japanese cypress, Japanese parsley, willow violet , Konagi, Ibokusa, Hoshikusa,
Japanese chickweed, common Japanese chickweed, common Japanese chickweed, common Japanese chickweed, Japanese commonweed, common Japanese chickweed, common Japanese chickweed, common Japanese chickweed, common Japanese chickweed, common Japanese chickweed, common Japanese chickweed, Japanese chickweed
These are paddy field weeds such as Japanese red pepper, sour pepper, Abnome azalea, and red pepper. In addition, weeds in the fields include, for example, blackberry, hackberry, pigweed, Japanese knotweed, cyperus japonica, cyperus japonica,
Japanese clover, red clover, oxalis,
It can be applied to sparrow peas, sycamores, yaemugura, noasagao, kawaraketsumei, crow peas, eggplants, etc. Furthermore, since the compound represented by the general formula () of the present invention affects the growth of plants, it can also be used as a defoliant, a germination inhibitor, and a growth regulator. The manner of use of the general formula () of the present invention is not particularly limited, and the manner of use of known herbicides can be used as is. For example, granules, powders, emulsions, wettable powders,
It can be used in any dosage form such as tablets, oils, aerosols, smokes, etc. Of course, auxiliary agents for formulation, such as spreading agents, diluents, surfactants, solvents, etc., can also be added as appropriate. The compound represented by the general formula () of the present invention can also be used in combination with insecticides, fungicides, other agricultural chemicals, fertilizer substances, soil improvers, and the like. EXAMPLES In order to explain the present invention more specifically, Examples and Comparative Examples will be described below, but the present invention is not limited to these Examples. Example 1 N-chloromethyl-chloroaceto-2,6-dimethylanilide (15 mmole 4.11 g) was converted into N,N-
Dimethylformamide (hereinafter abbreviated as DMF)
Dissolve in 10 ml of 2,2-dichloro-3,3-dimethylcyclopropyl methanol (15 mmole,
A solution of 2.54 g) dissolved in DMF (10 ml) was slowly added dropwise while stirring. A solution of triethylamine (18 mmole, 1.82 g) in DMF (10 ml) was then added dropwise with stirring, and the reaction mixture was stirred at 100° C. for 20 hours. After cooling to room temperature,
DMF and excess dryethylamine were distilled off, the residue was extracted with ether, and the ether layer was dried with sodium sulfate. The ether was distilled off, and the residue was recrystallized with hexane to obtain white plate crystals (3.01 g). The isolated product was determined to be N-(2',2'-dichloro-3',3'-dimethylcyclopropylmethoxymethyl)-chloroaceto-
It was confirmed that it was 2,6-diethylanilide. (b) IR The IR chart was as shown in Figure 1 of the attached drawings. From Figure 1, absorption based on carbon-hydrogen bond of aromatic ring is at 3100-3000 cm ^-1 , 3000-2850
Absorption based on aliphatic carbon-hydrogen bonds in cm ^-1 ,
Strong absorption based on the carbon-oxygen double bond of the amide compound appears at 1670 cm ^-1 , absorption based on the carbon-oxygen bond of the ether bond appears at 1090 cm ^-1 , and absorption based on the carbon-chlorine bond appears at 750 cm ^-1 . (b) ( ^13C -NMR, tetramethylsilane standard,
Sppm) Figure 2 of the attached drawings shows a ¹³ C-NMR chart. A peak based on the carbonyl carbon atom at 167.9ppm, a peak based on the carbon atoms at the 2nd and 6th positions of the benzene ring at 141.7ppm,
A peak based on the carbon atom at the 1st position of the benzene ring at 137.4ppm, a peak based on the carbon atom at the 4th position of the benzene ring at 129.4ppm, a peak based on the carbon atoms at the 3rd and 5th positions of the benzene ring at 127.0ppm,
A peak based on the methylene carbon atom sandwiched between nitrogen and ether bonded oxygen at 79.5ppm,
to 70.3ppm

[Formula] During bonding

The peak based on the carbon atom of [Formula], to 67.3ppm

[Formula] Peak based on methylene carbon atom in bond,
to 42.1ppm

[Formula] Peak based on methylene carbon atom in bond, at 37.5 ppm

[Formula] Carbon atom of methylene in bond peak based on, 29.0ppm

[Formula] Peak based on the carbon atom marked * in the bond,
to 24.7ppm

[Formula] A carbon-based peak based on the equatorial CH ₃ group in the bond,
A peak based on the methylene carbon of the ethyl group substituted at the 2nd and 6th positions of the benzene ring at 23.9ppm,
to 17.4ppm

[Formula] Peak based on carbon of axial CH ₃ group in bond and
At 14.5 ppm, a peak based on the methyl carbon of the ethyl group substituted at the 2nd and 6th positions of the benzene ring is shown. (3) Mass (m/, 20ev) As a result of mass measurement, the following peaks were observed. 406, 408 and 410 (M ⁺ ), 340, 342 and
344 [M ⁺ − (CH ₂ Cl + O)], 238 and 240

[Formula] 79 and 81 [ClCH ₂ Co ) (4) Elemental analysis Elemental analysis values are: carbon 56.20wt%, hydrogen 6.40wt%
%, nitrogen 3.70wt% chlorine 25.98wt%,
Theoretical values of C ₁₉ H ₂₆ NO ₂ Cl ₃ (molecular weight 406, 774): carbon 56.10wt%, hydrogen 6.44wt%, nitrogen 3.44wt
% and chlorine 26.14wt%. That is, from the above measurement results, the structure of the product obtained in this example is N-(2',2'-dichloro-3',
The product was confirmed to be 3'-dimethylcyclopropylmethoxymethyl)chloroaceto-2,6-diethylanilide. Note that the structures of the products in the following examples were also determined by the same method as above. Example 2 Dimethyl sulfoxide (hereinafter abbreviated as DMSO) was used instead of DMF as the solvent in Example 1.
The reaction and post-treatment were carried out in the same manner as in Example 1 except that 3.00 g of the same product as that obtained in Example 1 was obtained. Example 3 The reaction and post-treatment were carried out in the same manner as in Example 1 except that the reaction temperature was 50° C. and the reaction time was 2 hours. Results Example 1
1.5 g of product identical to that obtained in . Example 4 2,2-dichloro-3,3- in Example 1
2 instead of dimethylcyclopropylmethanol
2-dichlorocyclopropylmethanol (15m
The reaction was carried out in the same manner as in Example 1, except that mol) was used. As a product, 2.50 g of a colorless transparent liquid (which solidified if left standing in a cool, dark place for a long time) was obtained. Elemental analysis values are carbon 53.50wt%, hydrogen 5.85wt%, nitrogen
It was 3.81wt% chlorine 28.11wt%, which matched the theoretical values of C ₁₇ H ₂₂ NO ₂ Cl ₃ of 53.92 wt% carbon, 5.86 wt% hydrogen, 3.70 wt% nitrogen, and 28.08 wt% chlorine. moreover
Considering the results of instrumental analysis such as ^13C -NMR, IR, Mass, etc., the product is N-(2',2'-dichlorocyclopropylmethoxymethyl)-chloroaceto-2,
It was confirmed that it was 6-diethylanilide. Example 5 Same as Example 1 except that N-chloromethyl-chloroaceto-2,6-dimethylanilide (15 mmol) was used instead of N-chloromethyl-chloroaceto-2,6-diethylanilide in Example 1. When the reaction was carried out, 1.98 g of a white solid was obtained as a product. The elemental analysis values are carbon 53.63wt%, hydrogen 5.87wt%, nitrogen 3.83wt%, chlorine 27.89wt%, and the theoretical value of C ₁₇ H ₂₂ NO ₂ Cl ₃ is carbon 53.92wt%.
%, hydrogen 5.86wt%, nitrogen 3.70wt%, chlorine 28.08wt
% matched. Taking these results into consideration and the results of instrumental analysis conducted in the same manner as in Example 1, the structure of the product was determined as N-(2',2'-dichloro-3',3'-dimethylcyclopropylmethoxymethyl). -chloroacet-2,
It was confirmed that it was 6-dimethylanilide. Example 6 General formula () The compound represented by (R ₁ , R ₂ , and X are each listed in Table 1) (15 mmol) was dissolved in DMF (10 ml), and the general formula () A solution of the compound represented by (R ₃ , R ₄ and Y are listed in Table 1) (15 mmol) in DMF (10 ml) was slowly added dropwise while stirring. By treating the reaction mixture in the same manner as in Example 1, the general formula () A product represented by (R ₁ , R ₂ , R ₃ , R ₄ and Y are listed in Table 1) was obtained.

[Table] Formulation example 1 (hydrating powder) N-(2',2'-dichloro-3',3'-dimethylcyclopropylmethoxymethyl)-chloroaceto-2,6-diethylanilide obtained in Example 1 20 parts, Zincrite and Kunilite (Product name:
75 parts of a 2:1 mixture of clay minerals (manufactured by Kuniminesha),
The mixture was mixed with 5 parts of Solbol 800 (trade name: manufactured by Toho Chemical Industry Co., Ltd.) as a surfactant and ground to obtain a 20% hydrating powder. Formulation Example 2 (Emulsion) N-(2',2'-dichlorocyclopropylmethoxymethyl)-chloroaceto- obtained in Example 4
2,6-diethylanilide 20 parts, xylene 70 parts,
10 parts of Solbol 800 as a surfactant was mixed and dissolved to obtain a 20% emulsion. Formulation example 3 (granules) N-(2',2'-dichloro-
After mixing and pulverizing 5 parts of 3',3'-dimethylcyclopropylmethoxymethyl)-chloroaceto-2,6-dimethylanilide, 50 parts of bentonite, 40 parts of Kunilite, and 5 parts of Solbol 800 as a surfactant, 10 parts of water was added. Add it, stir it evenly, make it into a paste, extrude it through a sieve hole with a diameter of 0.7 mm, and after drying, 1-2
It was cut into lengths of mm to obtain 5% granules. Example 7 A 1/8850 are porcelain pot was filled with paddy soil (alluvial soil) that had been stirred with water, and after sowing paddy weeds, rice seedlings (variety: Nihonbare) at the 1.5 leaf stage were planted at a depth The plants were transplanted to a depth of 1 cm and water was added to make them submerged to a depth of 3 cm. Next, a predetermined amount of a water diluted solution of a hydrating powder of each compound prepared according to Formulation Example 1 was dropped upon germination of weeds. After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and the herbicidal effects of each test compound were investigated three weeks later. The results are shown in Table 2. The evaluation is in 11 stages, with 0 indicating normal, 1 to 9 indicating an intermediate stage between normal and complete withering, and 10 indicating complete withering.

【table】

[Table] Comparative Example The herbicidal effect of the control compound was investigated in the same manner as in Example 7. The results are shown in Table 3.

【table】

[Table] Example 8 Fill a 1/8850 are porcelain pot with paddy soil (alluvial soil) that has been stirred with water, and add water.
After the water is flooded to a depth of cm, rice and wildflower seeds are sown.
When the plants grew to the 0-leaf stage (at the time of germination), a predetermined amount of a water diluted solution of a hydrating powder of each compound prepared according to Formulation Example 1 was added dropwise. After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and the herbicidal effects of each test compound were investigated two weeks later. The investigation results are shown in Table 4 along with comparative examples of control compounds. Note that the criteria for the herbicidal effect in Table 4 are the same as in Example 7.

【table】

[Table] Example 9 Field soil (plant soil) in a 1/8850 are porcelain pot
Seeds of various plants were sown to a depth of 0.5 to 1 cm, and a predetermined amount of a water diluted solution of a wettable powder of each compound prepared according to Formulation Example 1 was sprayed onto the surface of the soil.
After treatment, the plants were grown in a greenhouse at an average temperature of 25°C, and the herbicidal effects of each test compound were investigated three weeks later. The results of the investigation are shown in Table 5 along with comparative examples of reference compounds. Note that the criteria for the herbicidal effect in Table 5 are the same as in Example 7.

【table】

【table】

【table】 [Brief explanation of drawings]

Figure 1 is an IR chart of the compound obtained in Example 1, and Figure 2 is an IR chart of the compound obtained in Example 1.
^13C -NMR charts are shown.

Claims (1)

[Claims] 1 General formula, N-substituted-chloroacetanilide represented by (In the formula, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, and R ₃
and R ₄ each represent the same or different hydrogen atom or methyl group, and Y represents a hydrogen atom or a chlorine atom. ) 2 N-substitution represented by the general formula, [Formula], characterized by reacting an N-halomethyl-chloroacetanilide represented by the general formula, [Formula] with an alcohol represented by the general formula, [Formula] -Process for producing chloroacetanilide. ₍ In _{the formula ,} (Y represents a hydrogen atom or a chlorine atom.) 3 A herbicide containing an N-substituted chloroacetanilide represented by the general formula, [Formula] as an active ingredient. (In the formula, R ₁ and R ₂ each represent the same or different methyl group, ethyl group, or halogen atom, and R ₃
and R ₄ each represent the same or different hydrogen atom or methyl group, and Y represents a hydrogen atom or a chlorine atom. )