JPH0273058A - Aniline derivative, preparation, use and intermediate thereof and preparation of said intermediate - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [X is H or F; Y is halogen; Z is -OCH2COOR1 (R1 is lower alkenyl, lower alkynyl, etc.,), -SCH2COOR2 (R2 is lower alkyl, lower alkenyl, etc.,), etc.; W is O or methylene]. EXAMPLE:8- (4-Chloro-2-fluoro-5-isopropylthiophenyl) -5-isopropylidene-1,3-oxa- zoline-2,4-dione. USE:A herbicide. The compound of formula I exhibits excellent selectivity be tween crop plants and weeds. PREPARATION:A carbamate derivative of formula II (R4 is lower alkyl) is cyclized in the presence of a base (e.g. K2CO3 or sodium methylate) to provide the compound of formula I (W is O).

Description

Detailed Description of the Invention [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH, COOR1,
-5CH, COO represents a group represented by an island or 18l, where R1 represents a lower alkenyl group, a lower alkynyl group or a lower cycloalkyl group, and an island represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or It represents a lower cycloalkyl group, and R3 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group. ), W represents an oxygen atom or a methylene group. ] The aniline conductor C shown in the following is hereinafter referred to as the compound of the present invention. ), its production method, a herbicide characterized by containing it as an active ingredient, an intermediate of the compound of the present invention, and a production method of the intermediate.

As a result of intensive studies aimed at developing an excellent herbicide, the inventors of the present invention have found that the compound of the present invention represented by the above general formula [phantom] exhibits excellent herbicidal activity and excellent selectivity between crops and weeds. This discovery led to the present invention.

The compounds of the present invention can be used to treat various weeds that are problematic in foliar and soil treatments in upland areas, such as buckwheat weeds, snail knotweed, sperihus, chickweed, whiteweed, blue radish, daikon radish, field mustard, American hornwort, Ebisu grass, Japanese thornweed, Japanese goldenrod, Field pansies - broad-leaved weeds such as Japanese morning glory, morning glory, common morning glory, European bindweed, white-winged morning glory, white-eared morning glory, white-spotted fern, Japanese fir, sunflower, dog's chamomile, corn marigold, spurge, etc., barnyard grass, Japanese millet, foxtail grass, blackberry, silver grass, The compound of the present invention has a herbicidal effect on grass weeds such as sycamore, oat, oat, seiban sorghum, grasshopper, horseweed, sorghum, and sorghum, as well as weeds of the family Cyperaceae such as dayflower, and weeds of the cyperus family such as cyperus japonica. It does not cause any harmful effects on major crops such as corn, wheat, barley, rice, soybeans, peanuts, cotton, and turgid gum.

In addition, the compound of the present invention can be applied to various weeds that are a problem in the waterlogging treatment of rice fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, japonica, and chickweed; It has a herbicidal effect on plants such as rice, and there are also questions about rice.

\ \ Next, the method for producing the compound of the present invention will be explained.

[Manufacturing method (a)]

Among the compounds of the present invention, W is an oxygen atom [wherein, X
2. SY and Z represent the same meanings as above, and group represents a lower alkyl group. ] Carbamate 85 conductor (hereinafter referred to as carbamate derivative [river]) can be produced from Iζ by cyclizing it in the presence of a base in a solvent.

The soot used in the above reaction includes benzene,
Examples include aromatic hydrocarbons such as toluene and xylene, ethers such as dioxane and ethylene glycol-5 dimethyl ether, fatty acids such as formic acid and acetic acid, water, and mixtures thereof.

Examples of the base used in the above reaction include potassium carbonate and sodium methylate, and these may be used in catalytic amounts.

The reaction temperature in the above reaction is about 0 to 200°C, and the reaction time is about 1 to 24 hours.

After the reaction is completed, the reaction solution is subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, chromatography,
The desired compound of the present invention can be obtained by purification by operations such as recrystallization.

[Manufacturing method (g)]

Among the compounds of the present invention, the compounds in which W is a methylene group are:
General formula [wherein, X, Y, and Z represent the same meanings as above]. ] It can be produced by condensing the aniline derivative represented by these with terraconic acid or terraconic anhydride.

The amount of the reagent in the above reaction is 1 to 1.2 equivalents of terraconic acid or terraconic anhydride per equivalent of the aniline derivative represented by the general formula (capital).

The above reaction can be carried out without a catalyst or with an inorganic base such as potassium carbonate, sodium carbonate, or sodium hydrogen carbonate, or an organic base such as triethylamine, pyridine, N,N-diethylaniline, etc., without a solvent or with acetic acid, toluene, 0-dichlorobenzene, It is carried out in a solvent such as N,N-dimethylformamide or dimethyl sulfoxide.

The reaction temperature in the above reaction is about 100 to 200°C, and the reaction time is about 1 to 24 hours.

Post-treatment after the completion of the reaction can be carried out in the same manner as in the case of production method (a).

[Manufacturing method (C)]

Among the compounds of the present invention, Z is monosoft -oCH2C00R.

(Here, R1 represents the same meaning as above.) A compound represented by -soft formula [wherein, X% Y and W represent the same meaning as above, and bird represents a lower alkyl group represent. ] In the aniline conductor represented by -soft formula % c formula, R8 represents the same meaning as above. It can be produced by reacting with an alcohol derivative shown in ].

The amount of the reagent in the above reaction is 1 equivalent or more of the alcohol derivative represented by the 1 soft form t+V+ for 1 equivalent of the aniline derivative represented by the 1 soft form t+V+.

The above reaction is carried out without a catalyst or with an inorganic acid such as hydrochloric acid or sulfuric acid or an organic acid such as acetic acid or p-)luenesulfonic acid as a catalyst, without a solvent or in a solvent such as acetic acid, benzene, toluene, or tetrahydrofuran.

The above reaction is carried out at room temperature to solvent reflux temperature and is about 1 to 24
Finish in time.

Post-treatment after the completion of the reaction can be carried out in the same manner as in the case of production method (a) [Production method (d)] Among the compounds of the present invention, Z is of the general formula -5CH, C00R4
(Here, R2 represents the same meaning as above.) A compound represented by -soft formula [wherein, X, Y and W represent the same meaning as above, and bird represents a lower alkyl group] . ] and the aniline derivative represented by -soft formula % (5) [wherein R8 represents the same meaning as above. It can be produced by reacting with an alcohol derivative shown in ].

The amount of the reagent in the above reaction is 1 equivalent or more of the aniline derivative represented by -soft, and 1 equivalent or more of the alcohol derivative represented by -soft. Other reaction conditions and the like are the same as in production method (C).

The following is a production example of the compound of the present invention.

Production Example 1 ■-Methoxycarbonyl-2-methylallyl N-(4-
Chloro-2-fluoro-5-isopropylthiophenyl)carbamate 4.22 and sodium methylate 0
．． 2f was added to 100 mJ of benzene, and the mixture was heated under reflux for 8 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was purified by column chromatography and 8
-(4-10rho2-fluoro-5-isopropylthiophenyl)-6-itubropylidene-1,8-oxazolidine-2,4-dione 2.92 was obtained.

mp 185-140°C Production Example 2 In the same manner as Production Example 1, 1-methoxycarbonyl-2-
Methylallyl N-(4-chloro-2-fluoro-5-
8-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-6-itubropylidene-1,8-oxazolidine-2,4-dione was obtained from methoxycarbonylmethylthiophenyl)carbamate.

NMRδ [solvent: CDC4, internal standard: TMS)7.
75 (d, IH) 7.60 (d, xH) 8.92
(s, 2H) 8.60(s, 8)f) 2.21(
s, 8H) 2.00 (s.

8H) Production Example 8 4-chloro-2-fluoro-5-isopropylthioaniline 8. OF and terraconic anhydride 2.12 to acetic acid 10
0 ml and heated under reflux for 3 hours.

After cooling, the reaction mixture was poured into water and extracted with ethyl acetate.

The organic layer was purified by column chromatography (developing solvent: hexane-ethyl acetate mixture), and N-(4-chloro-
2-Fluoro-5-isopropylthiophenyl)teraconic acid imide 822 was obtained.

NMRδ [Solvent: CDC/3. Internal standard: TMS, ]7
．． 81(s, IH) 7.20(s, 1f() 8
．． 15-8.60 (rn, 8H) 2.88 (S, 8
E () 1.95 (3,8H) 1.30 ((l,
6H) Production Example 4 8-(4-chloro-2-fluoro-5-methoxycarbonylmethoxyphenyl)-5-isopropylidene-1,
8-oxazolidine-2°4-dione 1.02, cyclopentanol 20 ml and p-1 luenesulfonic acid 0
．． The 1F mixture was heated to reflux for 8 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was purified by column chromatography to obtain 8-(4-chloro-2
-fluoro-5-cyclopentyloxycarbonylmethoxyphenyl)-5-isopropylidene-1,8-oxazolidine-2°4-dione 0.8F was obtained.

NMRδ [solvent: CDCjs*internal standard: TMS]7.
80 (d, IH) 6.82 (d, IH) 5.1
0-5,40 (br, IH) 4.60 (s, 2H)
2.25 (s, 8H) 2.02 (s, 8H) 1.
40-1.95 (br, 8H) Production Example 5 In the same manner as Production Example 4, 8-(4-chloro-2-fluoro-5-methoxycarbonylmethoxyphenyl)-5-
Isopropylidene-1,8-oxazolidine-2,4-
8-(4-chloro-2-fluoro-5-allyloxycarbonylmethoxyphenyl)-5-isopropylidene-1,8-oxazolidine-2,4-dione was obtained from the dione.

NMRδ [Solvent: CDCl5. Internal standard: TMS, 17
．． 80 (d, LH) 6.85 (d, IH) 5.0
0-6.40 (m, 8H) 4.65 (S, 2H) 4
．． 00 (2H) 2.25 (S, 8H) 2.02 (
S, 8H) Production Example 6 In the same manner as in Production Example 4, 8-(4-chloro-2-fluoro-5-methoxycarbonylmethoxyphenyl)-5-
Isopropylidene-1,8-oxazolidine-2,4-
8-(4-chloro-2-fluoro-5-propargyloxycarbonylmethoxyphenyl)-5-isopropylidene-1,8-oxazolidine-2°4-dione was obtained from the dione.

NMRδ [solvent: CDC45, internal standard: TMS]7.
25 (d, IH) 6.85 (d, IH) 4.7
5 (d, 2H) 4.66 (s, 2H) 2.50 (t, L
H) 2.25 (Se 88) 2.05 (S g
8H) Production Example 7 In the same manner as in Production Example 4, a-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-5
-isopropylidene-1゜8-oxazolidine-2,4
8-(4-chloro-2-fluoro-5-allyloxycarbonylmethylthiophenyl)-5-isopropylidene-1,8-oxazolidine-2°4-dione was obtained from the -dione.

NMRδ [solvent: CDCl3, internal standard: TMS) 7
．． 40 (d, IH) 7.28 (d, IH) 5.0
0-6.80 (m, 8H) 4.05 (d, 2H) 4
．． 00 (s, 2H) 2.80 (s, 8H) 2.05
(s, 8H) Next, the carbamate derivative (3) which is an intermediate of the compound of the present invention will be explained.

Carbamate derivatives include, for example, the compounds shown in Table 2 below.

The above carbamate derivative (9) is a useful compound because it is not only an intermediate for the compound of the present invention, but also can be used as a herbicide.

Next, a method for producing carbamate derivative (4) will be explained.

[Manufacturing method (d)]

The carbamate derivative (5) has the general formula [wherein, X1Y and Z have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula % formula % [wherein 艮 represents the same meaning as above. It can be produced by condensing alcohol derivatives represented by the following formulas.

The amount of the reagent in the above reaction is 1 to 1.2 equivalents of the alcohol derivative represented by the general formula (2) per 1 equivalent of the phenyl isocyanate derivative represented by the general formula (4).

The above reaction can be carried out without catalyst or using triethylamine, N,N-diethylaniline, 1,4-diazabicyclo(2,2,2
) The reaction can be carried out without a solvent or in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, carbon tetrachloride, etc. using octane or the like as a catalyst.

The reaction can be completed instantly in 10 hours by cooling or heating (0 to 50° C.) as necessary, and the desired product can be obtained.

Note that the phenyl isocyanate derivative represented by the general formula (4) can be obtained by reacting the aniline derivative represented by the general formula (2) with phosgene.

The amount of the reagent in the above reaction is 8 to 10 equivalents of phosgene per equivalent of the aniline derivative represented by general formula (4).

The above reaction is carried out in an organic solvent such as benzene, toluene, xylene, ethyl acetate or a mixture thereof. The reaction can be carried out by heating from 50°C to reflux temperature as necessary.
The process can be completed in 10 hours rather than instantaneously, and the desired product can be obtained in good yield.

Furthermore, the alcohol derivatives shown in the -soft diagram are described, for example, in the literature (J, Am, Chem, Soc, 955
58 (1978)').

Next, the method for producing carbamate-induced closure will be explained in detail by giving a production example.

Production Example 8 4-chloro-2-fluoro-6-itubrobylthiophenyl isocyanate 2.5f and 2-hydroxy-8
-Methyl-8-butenoate 1.82 to benzene 50
Dissolved in mJ. 0.52% of triethylamine was added at room temperature, and the mixture was gradually heated and refluxed for 1 hour. After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate.
-methoxycarbonyl-2-methylallyl N-(4-
Chloro-2-fluoro-5-isopropylthiophenyl)carbamate 8.1 F+ was obtained.

NMRδ [solvent: CDCJ, internal standard: TMS)7.
80 (d, 1) I) 7.22 (d, LH) 5.
85 (s, IH) 4.90-5.10 (2H) 8
．． 80 (s, 8H) 1.70 (S, 8I () 1.4
0(d,6H) When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, liquid carrier, surfactant, or other formulation auxiliary to form an emulsion, wettable powder, or suspension. , formulated into granules, etc.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of about 0.05 to 90%, preferably about 0.1 to 80%.

Examples of solid carriers include fine powders or granules such as kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut shell powder, ice-based materials, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl sulfoxide. ,N,
Examples include N-dimethylformamide, acetonitrile, water and the like.

Surfactants used for emulsification, dispersion, wet carbonization, etc. include anionic interfaces such as alkyl sulfate salts, alkylaryl sulfone'm salts, dialkyl sulfosuccinates, and polyoxyethylene alkylaryl ether phosphate salts. Examples include activators, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxybrobylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Formulation adjuvants include lignin sulfonate, alginate, and polyvinyl alcohol.

Gum arabic, CMC (carboxymethyl cellulose)
, PAP (isopropyl acid phosphate), and the like.

Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts indicate parts by weight.

Formulation Example 1 50 parts each of compound (8), (4), (5), (6) or (7), 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrated silicon oxide were thoroughly ground. Mix to obtain respective hydrating agents.

Formulation Example 2 Compound (12) or (19> 5 parts each, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 80 parts of xylene and 45 parts of cyclohexanone are mixed well to obtain each emulsion. .

Formulation Example 8 Compound (3), (4), (5) or (6), 2 parts each, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay
After thoroughly grinding and mixing, add water and mix thoroughly,
The granules are dried to obtain granules.

Formulation Example 4 Compound (7), (12) or (19), 25 parts each,
8 parts of polyoxyethylene sorbitan monooleate, C
8 parts of MC and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain respective suspensions.

Formulation Example 5 Compounds (a), (4), (5), (6), (7), (1
2) or (19), 5 parts each, 14 parts polyoxyethylene styrylphenyl ether, 6 parts calcium dodecylbenzenesulfonate, 80 parts xylene and N.

45 parts of N-dimethylformamide were thoroughly mixed to obtain each emulsion.

The compound of the present invention thus formulated is treated with soil, foliage, or flooding before or after the emergence of weeds. Earthen wall treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body as well as local treatment that treats only weeds so that they do not attach to crops.

Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.

The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in herbicides for lawns, forests, non-agricultural lands, etc.

When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
Approximately 0.02f to 100y per are, preferably
Approximately 0.05f to 502, and emulsions, wettable powders, suspension agents, etc. are usually used in a predetermined amount of about 1 liter to 1 liter per are.
It is diluted with 0 liters of water (if necessary, auxiliary agents such as spreading agents are added) for treatment, and granules and the like are usually treated as they are without any dilution.

In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene resin acid (ester), lignin sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, and paraffin.

Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 8.

Table 8 In addition, herbicidal efficacy is determined by visually observing the degree of budding and growth inhibition of the test plants during the survey, and ``0'' indicates that there is no or almost no difference from the case where no compound is used. The plant is rated on a scale of 0 to 5, with "5" indicating that the plant has died or its growth has been completely inhibited.
8.4.6.

Test Example 1 Upland Soil Treatment Test Ten cylindrical plastic pots with a diameter of 10 ml and a depth of 10 ml were filled with upland soil, sown with Japanese barnyard grass, Japanese morning glory, and Japanese crocodile, and covered with soil. The test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 4.

Table 4 Test Example 2 Upland Grass Treatment Test A cylindrical plastic pit with a diameter of 10 cIR and a depth of 10 G was filled with upland soil, sown with morning glory and Ichibi, and grown in a greenhouse for 10 days.

Thereafter, the test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. . After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in table @5'.

Table 1 Test Example 3 Upland Stem and Leaves Treatment Test A cylindrical plastic pot with a diameter of 10 m and a depth of 10 cnt is filled with upland soil, sown with radish, and placed in a greenhouse for 10 m
It was grown for days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2 or 5, and a predetermined amount of 10
It was diluted with water containing a liter of spreading agent and treated with a small sprayer from above the plant. 20 days after treatment! ! J
It was grown in a greenhouse and its herbicidal efficacy was investigated. The result is the 6th
Shown in the table.

Test Example 4 Paddy field flooding treatment test diameter 8c! Fill a cylindrical plastic pot with IM1 depth 12c111 with paddy soil and add 1 to 100 Tianubiena seeds.
Mixed to a depth of 20. After turning black water into paddy fields,
Tubers of Urikawa were buried 1 to 2 depths and grown in a greenhouse. Six days later (at the beginning of each weed's emergence), the test compound was made into an emulsion according to Formulation Example 2 or 5, a predetermined amount of the emulsion was diluted with 5 milliliters of water, and the emulsion was applied to the water surface. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 7.

@ 7 tables. Herbicidal efficacy and phytotoxicity were investigated 17 days after treatment. The results are shown in Table 8. Note that this test was conducted in a greenhouse throughout the entire period.

Test Example 5 Field soil stem and leaf treatment test A vat with an area of 26 x 18 ajt and a depth of 8α was filled with field soil, and soybean, Japanese morning glory, Japanese fir tree, and Japanese physalis were sown and grown for 16 days.

Then, make an emulsion of the test compound according to Formulation Example 2, dilute the specified amount with water equivalent to 5 liters per are containing a spreading agent, and use a small sprayer to spread it evenly over the entire stem and leaf area from above the plant body. processed.

At this time, the growth conditions of weeds and crops vary depending on the grass species, but the 1 to 4 leaf stage and the plant height are 2 to 120 ＼ ＼ ＼＼ ゝ＼ ＼, ＼

Claims (8)

[Claims] (1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH_2COOR_1, -SCH_2COOR_2
or represents a group represented by -SR_3 (where R_1
represents a lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, R_2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, and R_3 represents a lower alkyl group, lower alkenyl group, or lower alkynyl group. , represents a lower haloalkyl group or a lower alkoxyalkyl group. ), W represents an oxygen atom or a methylene group. ] Aniline derivative represented by. (2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH_2COOR_1, -SCH_2COOR_2
or represents a group represented by -SR_3 (where R_1
represents a lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, R_2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, and R_3 represents a lower alkyl group, lower alkenyl group, or lower alkynyl group. , represents a lower haloalkyl group or a lower alkoxyalkyl group. ) R_4 represents a lower alkyl group. ] General formula ▲ Numerical formula, chemical formula, table, etc., characterized by cyclizing the carbamate derivative represented by the above in the presence of a base ▼ [In the formula, represent. ] A method for producing an aniline derivative represented by (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH_2COOR_1, -SCH_2COOR_2
or represents a group represented by -SR_3 (where R_1
represents a lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, R_2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, and R_3 represents a lower alkyl group, lower alkenyl group, or lower alkynyl group. , represents a lower haloalkyl group or a lower alkoxyalkyl group. ). ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting the aniline derivative represented by the above with terraconic acid or terraconic anhydride ▼ [In the formula, X, Y and Z are the same as above express meaning. ] A method for producing an aniline derivative represented by (4) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, W represents an oxygen atom or a methylene group, and R_5 is a lower alkyl represents a group. ] An aniline derivative represented by the general formula R_1-OH [wherein R_1 represents a lower alkenyl group, a lower alkynyl group, or a lower cycloalkyl group]. [In the formula, X, Y, W and R_1 represent the same meanings as above. ] A method for producing an aniline derivative represented by (5) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, W represents an oxygen atom or a methylene group, and R_5 is a lower alkyl represents a group. ] Aniline derivatives represented by the general formula R_2-OH [wherein R_2 is a lower alkyl group, a lower alkenyl group,
Represents a lower alkynyl group or a lower cycloalkyl group. [In the formula, X, Y, W and R_2 represent the same meanings as above. ] A method for producing an aniline derivative represented by (6) A herbicide containing the aniline derivative according to claim 1 as an active ingredient. (7) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH_2COOR_1, -SCH_2COOR_2
or represents a group represented by -SR_3 (where R_1
represents a lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, R_2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, and R_3 represents a lower alkyl group, lower alkenyl group, or lower alkynyl group. , represents a lower haloalkyl group or a lower alkoxyalkyl group. ), R_4 represents a lower alkyl group. ] A carbamate derivative represented by (8) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a hydrogen atom or a fluorine atom, Y represents a halogen atom, and Z represents the general formula -OCH_2COOR_1, -SCH_2COOR_2
or represents a group represented by -SR_3 (where R_1
represents a lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, R_2 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower cycloalkyl group, and R_3 represents a lower alkyl group, lower alkenyl group, or lower alkynyl group. , represents a lower haloalkyl group or a lower alkoxyalkyl group. ). ] There are phenyl isocyanate derivatives shown by the general formula ▲ numerical formula, chemical formula, table, etc. ▼ [In the formula, R_4 represents a lower alkyl group. 8. The method for producing a carbamate derivative according to claim 7, which comprises reacting the carbamate derivative with an alcohol derivative represented by the following.