JPS58216175A - Substituted urea derivative and its preparation, intermediate for preparing the same, preparation thereof and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X and Y are halogen or together with a heterocyclic ring to which they are linked may form benzo-condensed heterocyclic ring; A and B are O or S; R is CH3 or OCH3). EXAMPLE:1,1-Dimethyl-3-[4-(4,5-dichloro-2-thiazolyloxy)phenyl]urea. USE:A herbicide effective particularly against broad-leaved weeds in the cultivation of leguminous plants. PROCESS:A compound of formula II is reacted with a compound of formula IIIor a compound of formula IV is reacted with a compound of formula V in an inert solvent or diluent at 0-100 deg.C and ordinary pressure to give the aimed compound of formula I . The compounds of formulas II and IV are novel substances.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel substituted phenylurea derivatives, intermediates for their production, processes for producing the derivatives and intermediates, and herbicides.

More specifically, the present invention relates to a substituted phenylurea derivative represented by the following general formula (1). That is, the general formula: % Formula % In the formula, X and Y each represent a rhodane atom, and X and Y, together with the heterocycle to which they are bonded, form a benzo-fused heterocycle. The whole can be formed, where:
The benzo-fused complex term is... The rhodan atom and lower A and B each represent an oxygen atom or a sulfur atom, and R represents a methyl group or a methoxylic group.

The substituted phenylurea derivative of the above general formula (1) of the present invention can be produced, for example, by the following method.

The invention also relates to the process. That is, Manufacturing method 1); General formula: %formula% In the formula, X, Y and A are the same as above, HalFi indicates a halogen atom, A compound represented by General formula: In the formula, B and R are the same as above, M represents a hydrogen atom or an alkali metal atom.

A method for producing a substituted phenylurea derivative of the general formula (1), which comprises reacting a compound represented by the formula (1).

Production method 11); A compound represented by the general formula: where X, Y, A and B are the same as above, and a compound represented by the general formula: where R and Hαl are the same as above are reacted. characterized by
A method for producing a substituted phenylurea derivative of the general formula (1).

Production method 1i); A compound represented by the general formula: where X, Y, A and B are the same as above, and a compound represented by the general formula: where R is the same as above, are reacted. Characterized by
A method for producing a #xyrophenylurea derivative of the general formula (1).

The present invention also relates to a herbicide containing the phenylurea derivative of the general formula (I) as an active ingredient.

Furthermore, the present invention also relates to the aniline derivative of the above general formula (IV), which is an intermediate for forming the substituted phenylurea derivative of the above general formula (1), and the phenyl isocyanate derivative of the above general formula (Vl).

The 64 anilines of the above general formula (1v) and the phenyl isocyanate derivatives of the above general formula (Vl) are each
For example, ``By the above method! The present invention also relates to the manufacturing method. That is, Production method 1■); characterized by reacting the compound represented by the general formula (1) with an aminophenol or a salt thereof represented by the general formula: where B and M are the same as above. A method for producing the aniline derivative of general formula (IV).

Production method v); A method for producing the phenyl isocyanate derivative of the general formula (■), which comprises reacting the aniline derivative represented by the general formula (fV) with phosdane or trichloromethyl chloroformate.

The purpose of this book is to create herbicidally active compounds, and 18
− Undertook experimental research.

The Ministry of the Invention and others have now successfully synthesized a substituted phenylurea derivative of the general formula (1), and found that the compound is a completely new compound that has not been described in any known literature, and that it has a useful herbicidal activity. I discovered that it is something.

According to the research of the present inventors, the general formula (1) of the present invention
The new compound can accurately kill and control undesirable weeds in the cultivation of useful crops such as soybean, cotton, corn, incandescent, rice, wheat, sugar beet, and peanut temple, and can also cause chemical damage to these useful crops. It has been discovered that this compound exhibits an excellent selective herbicidal effect that prevents herbivory. And the selectivity of the active compounds is, inter alia, Glycin
It has been found that both Pha-seolultf and Pha-seolultf exhibit extremely superior herbicidal activity against a spectrum of weeds that are undesirable in the cultivation of leguminous crops, especially broad-leaved hybrids.

The characteristics of the active compounds of the invention reside not only in the above-mentioned biological action but also in their structure. That is, the basic skeleton is phenyl urea, and to the phenyl group, a heterocyclic group as defined in the general formula (1) is ether-bonded to form a structure, and in particular, the heterocyclic group has more ambiguous activity when it is ether bonded at the meta- or iR-position of the phenyl group.

Furthermore, the aniline derivatives of the general formula (IV) of the present invention as well as the phenyl isocyanate derivatives of the general formula (Vl) are also novel compounds and proboscises that have not been described in the known literature, and as mentioned above, they have excellent properties. It is industrially useful as an intermediate for producing a novel active compound of the general formula (1) having selective herbicidal activity, and is particularly useful for the amino group in the general formula (1v) as well as the general formula ( Vl)
The incyanato group in is a phenyl group meta- or noe
The intermediate substituted at the - position is extremely useful industrially.

Therefore, the object of the present invention is to provide a novel aniline conductor of the general formula (1), a novel aniline conductor of the general formula (IVN) as a production intermediate thereof, and a new aniline conductor of the general formula (IVN) as a production intermediate thereof. The present invention provides a novel phenyl isocyanate derivative, a method for producing the derivative, and its use as a demulcent agent.

The above objects and many other objects and advantages of the present invention will become more apparent from the following description.

The herbicide of the present invention has low toxicity to warm-blooded animals and has good selectivity for cultivation tank I proboscis, that is, it has the characteristics that there is no phytotoxicity to cultivated plants at the usual concentration of 1. It can be advantageously used as an agent for weed control. When the weed remover of the present invention is used as a soil treatment agent for weeds in field cultivation before they sprout, or as a soil treatment agent for foliage and foliage, it exhibits excellent selective control efficacy.

As mentioned above, the active compound of the present invention is excellent in safety and exhibits an outstanding herbicidal effect, and has a wide herbicidal spectrum.

for example, Polygonum sp.

Chenopodil Lm alburn L
innaeusvar, centrorubrwm A
4akin.

Shiroza Chenopodiurn alburn L
innaeus hako-z Stellariawre
diaVillars1 Ohu Amaranthus
retrofLexus L.

Portulaca oleracea L
inner-eus.

Dogfish Aynαranthus asce? +den
s Loisel.

H:r-Echinochloa crus-gaLL
i P,Beartv.

υa, r.

Mehishiba I) igitaria adsce'rLd
c? ls Henr.

22- -/)-Y tree isu (4perus m1croiri
a 5teud.

Sagina ja, pon, ica Oh
wi Suka'/p Godeu Rorippa Palust
risBa5s.

Himesuipa Rumex Acetosella L.

CommeLina communis L
.

Sparrow Poa annwa L.

It has been recognized that it has a strong removal effect on plants such as 44. , e.g. overbarq sy (Cyperrts
ro tundus L.), etc., excellent weeding and locust control effects are also observed.

The compound '$lJ of the general formula (1) of the present invention can be produced, for example, in the methods 1), 11), and 111) of manure.

(B (1) (1) (where X, Y, A, B, R, l1aL and M(ti
@7 Same as myself. ) In the above reaction formula, X and Y respectively represent a halogen atom such as fluoro-1chlor; zolom; iodine, etc., and the separated X and Y are:
Together with the heterocycle to which they are attached, they can form benzo-fused heterocycles such as benzoxazole, benzothiazole, etc., where these rings contain the same halogen atoms as exemplified above, and For example, methyl; ethyl; propyl; isoprogyl; n-(1so-,5e
It may be substituted with at least one selected from the group consisting of a lower alkoxy group having a lower alkyl group having 1 to 4 carbon atoms such as c- or tert-)butyl.

A and B each represent a boron atom or a sulfur atom, R represents a methyl group or a methoxy group.

Examples of Hαl include halogen atoms similar to those exemplified above,
Preferred examples include chloro and bromine.

M represents, for example, a hydrogen atom or an alkali metal atom such as lithium; sodium; potassium, etc.

In the method for producing the compound of general formula N) of the present invention shown in the above reaction formula, specific examples of the compound of general formula (II) as a raw material include 2.4.5-trichlorothiazole, 2.4. 5-) Lichloroxazole, 2-chlorobenzothiazole, 2-chlorobenzoxazole, 2-chloro-6-fluorobenzothiazole, 25-2.4-nochlorpenzotheazole, 2.5.7-) IJ dichloro 6-nitoxopenzotheazole can be exemplified, and instead of the above-mentioned 2-chloro substituted product, 2-brome substituted product can also be mentioned.

Specific examples of the compound of general formula (1) in the above reaction formula, which is also a raw material, include 1.1--/methyl-3-(4-hydroxyphenyl)urea, 1.1-methyl-3- (3-hydroquinphenyl)urea, 1.1-methyl-3-(4-mercazotophenyl)urea, 1-methyl-1-methoxy-3-(4-hydroxyphenyl)urea, 1-methyl-1 Examples include -methoxy-3-(3-hydro-26-xyphenyl)urea.

Next, the above manufacturing method will be specifically explained using representative examples.

The above method can desirably be carried out using a solvent or diluent. For this purpose all inert solvents and diluents can be used.

Examples of such molten malt or diluent include water; aliphatic, cycloaliphatic, and aromatic carbonized scales (which may be diluted depending on the situation), such as hexane, cyclohexane, petroleum ether, ligroin, and benzene. , toluene, xylene, methylene chloride, chloroform, carbon tetracarbon,
Ethylene chlorite, trichlorethylene, chlorobenzene; other ether chains such as diethyl ether, methyl ethyl ether, di-180-propyl ether, subbutyl ether, propion oxide, dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl- 1so-globyl ketone, methyl-1so-butylketone; Nitriles such as acetonitrile, zolobionitrile, acrylonitrile; Alcohols such as methanol, ethanol,
1ao-zolono-7nol, butanol, ethylene glycol esters such as ethyl acetate, amyl acetate; acid amides such as trimethylformamide, trimethylacetamide; sulfones, sulfoxides such as zomethyl
Mention may be made of sulfoxide, sulfolane; and bases such as pyridino.

Also, as mentioned above, the reaction of the present invention is r++t l'l''
It can be carried out in the presence of a mixture. Such acid binders include commonly used alkali metals in water.
compounds, carbonates, bicarbonates, alcoholados, etc., and tertiary
For example, triethylamine, diethylaniline, birinone, etc. can be mentioned.

The method of the invention can be carried out within a wide temperature range. For example, the reaction can be carried out between about -20"C and the boiling point of the mixture, preferably between about 0 and about 100"C.Also, the reaction is preferably carried out under normal pressure, but under elevated pressure. Alternatively, it is also possible to operate under reduced pressure.

Production method 11): (It/> (V)29- (1) (In the formula, X, Y, A, B, R and J-1aL are the same as above.) In the above reaction formula, X, Y, A, Examples of B, R and HaL include those having the same meanings as described above.

In the method shown in the above reaction formula, specific examples of the compound of general formula (IV) as a raw material include 4-(4,5-dichloro-2-thiazolyloxy)aniline, 3-(4,5-dichloro) -2-thiazolyloxy)aniline, 4-(4,5-cyclo-2-oxazolyloxy)aniline, 4-(2-benzothiazolyloxy)aniline 53-(
2-Benzothiazolyloxy)aniline, 4-(2-benzoxasilyloxy)aniline, 3-(2-benzoxasilyloxy)aniline, 4-(6-fluoro-2-benzothiazolyloxy7) Aniline, 4-(4-chloro-2-benzothiazolyloxy)aniline, 4-(5,7-dichloro-6-nitoquine-2-benzothiazolyloxy)aniline, 4-(2-benzothiazolylthio) ) Aniline 4 can be exemplified.

Examples of the compound V1j of the general formula (V) which is a raw material for the isomer include all examples such as N-methyl-N-methoxycarbamoyl chloride, dimethylcarbamoyl chloride, etc., and bromide instead of the chloride. You can also display your body.

Next, we give a typical example and explain the above production method in detail. In order to carry out the above method, the same inert solvent or diluent as mentioned above is used to obtain the target product with high purity and high yield. I can do it. The process can also be carried out within a wide temperature range, for example between about -20°C and the boiling point of the mixture, preferably between about θ and about 100°C. Further, although the reaction is preferably carried out under normal pressure, it is also possible to operate under increased pressure or ld# pressure.

Production method ii): (■) (■) (1) (In the formula, X, Y, A, B and R are the same as above.) In the above reaction formula, examples of X, Y, A, B and R are , those having the same meaning as those described above can be exemplified.

33- In the method shown by the above reaction formula, specific examples of the compound of general formula (Vl) as a raw material include 4-(4,5-dichloro-2-thiazolyloxy)phenyl incyanate, 3-(4 , 5-dichloro-2-thiazolyloxy) phenyl isocyanate, 4-(4,5-cyclo-2-oxacylyloxy) phenyl isocyanate, 4-(2-benzothiazolyloxy) phenyl isocyanate, a-(g-benzothia Zolyloxy) phenyl isocyanate, 4-(2-pendio-xazolyloxy) phenyl icanate, 3-(2-benzooxasilyloxy) phenyl inocyanate, 34- 4-(6-fluoro-2-benzothiazolyl) oxy) phenyl isocyanate, 4-(4-chloro-2-benzothiazolyloxy) phenyl isocyanate, 4-(5,7-dichloro-6-ethoxy-2-benzothiazolyloxy) phenyl isocyanate, 4-( An example is 2-benzotheazolylthio)phenylisocyanate.

Similarly, specific examples of the compound of general formula (vl) which is a raw material include trimethylamine and N-methylmethoxyamineff1-IAI.

The above manufacturing method will be explained in detail by giving representative examples.

In order to carry out the above method, the same inert solvent or diluent as described above is used, and the desired product can be obtained with high purity and high yield. The above process can also be carried out within a wide temperature range, for example between about -20°C and the boiling point of the mixture, preferably from about 0°C to about 1°C.
It can be carried out between 00°C. Further, although it is preferable to carry out the reaction under normal pressure, it is also possible to operate under increased pressure or reduced pressure.

Furthermore, in the compound VC of the general formula (1) of the present invention, a compound of the following general formula (1) in which R is a methoxy group can also be produced by the following method.

That is, (IX) (In the formula, X, Y, A and B are the same as above.) In the above method iC, all examples of the methylating agent include egret, methyl iodide, diazomethane, dimethyl sulfate, etc. I can do it.

The above process can be carried out using the same inert solvents or diluents as described above and over a wide range of temperatures and pressures as described above.

Next, the aniline derivative of the general formula (IV) of the present invention, which is an intermediate for the production of the compound of the general formula (1), can be produced by the method iv) described below.

Production method 1v): (11) (In the formula, X, Y, A, B, Jial and M Vi are the same as above.) In the above reaction formula, examples of X, Y, A, B, HCl and M are @ Examples of the same meanings as those mentioned above can be given.

In the method shown by the above reaction formula, specific examples of the compound of general formula (11) as a raw material include the same compounds as those exemplified in the production method 1), and 38- can be obtained.

Similarly, specific examples of compounds of general formula (Vlll) which are raw materials include 3-aminophenol, 4-aminebenzenethiol, 4-aminophenol, etc. Alkali metal atoms such as salts, sodium salts, potassium salts, etc. can be mentioned.

Next, the above manufacturing method will be specifically explained using representative examples.

In order to carry out the above method, the same inert solvent freezing or diluent as described above is used, and the desired product can be obtained with high purity and high yield. Freezing The above method can be carried out within a wide temperature range, e.g.
It can be carried out between the boiling point of the substance, preferably about 0 to about t o
It can be carried out between 0°C and 0°C. Further, although it is preferable to carry out the reaction under normal pressure, it is also possible to operate under increased pressure or reduced pressure.

Similarly, the phenyl isocyanol 1 conductor of the general formula (■) of the present invention, which is a production intermediate, can be produced by the following method V).

Manufacturing method v): (IVI (wherein, X +' Y , A and B are the same as above)
In the above reaction formula, examples of X, Y, A and B are:
The same meanings as those mentioned above can be exemplified.

Regarding the method shown in the above reaction formula, the compound 8-compound of general formula ([V), which is a raw material, can be produced by the above-mentioned production method iv), and a specific example thereof is exemplified in the above-mentioned production method 11). All examples of compounds similar to the above can be shown.

In the above method, phosdan (COCl) can also be used instead of trichloromethyl chloroformate.

Next, the above manufacturing method will be specifically explained using representative examples.

41- In order to carry out the above method, the same inert solvent or diluent as described above except for water and alcohol may be used to obtain the desired product with high purity and high yield. Furthermore, the above method can be carried out within a wide temperature range,
For example, the reaction can be carried out between about -20"C and the boiling point of the mixture, preferably between about θ and about 100°C. However, the reaction is preferably carried out at normal pressure. It is also possible to operate under pressure or reduced pressure.

When the compound of the present invention is used as a herbicide, it can be used as it is, directly diluted with water, or it can be used in various ways using a pesticide auxiliary by a method commonly used in the field of pesticide manufacturing. It can be used in the form of a preparation. In actual use, these preparations A and 4 can be used directly as they are, or diluted with 42- or water to a desired concentration.

Examples of pesticide adjuvants mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, fixing agents, aerosols. Examples include propellants and synergists.

Solvents include water: organic solvents; hydrocarbons [e.g.
-Hexane, petroleum ether, naphtha, petroleum fractions (seven waxes, kerosene, light oil, medium oil, heavy oil), benzene, toluene, quince], halogenated hydrocarbons [e.g.
Chlormethylene, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene tribromide, chlorobenzene,
chloroform], alcohol M (for example, methyl alcohol, ethyl alcohol, flobyl alcohol, ethylene glycol), ether m [for example, ethyl ether, ethylene oxide, sooxane], alcohol ethers [for example, ethyl ether, ethylene oxide, sooxane], glycol monomethyl ether], ketones [e.g. acetone, isophorone], esters [e.g. ethyl acetate, amyl acetate], amides [e.g. dimethylformamide, dimethylacetamide], sulfoxides [e.g. dimethylsulfoxide)'e I can list many things.

Inorganic powders and granules as fillers or carriers; slaked lime, magnesium lime, gypsum, carbonate, silica, gillite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. phyllite, talc, montmorillonite, beidellite, vermiculite, kaolinite, mica): vegetable powder; grain flour, starch, modified starch, sugar, glucose, crushed plant stems: synthetic resin powder; phenolic resin, Examples include urea resin and vinyl chloride resin.

Examples of surfactants include anionic surfactants: natural agents; alkyl sulfate esters [e.g. sodium lauryl sulfate], arylsulfonic acids [e.g. alkylaryl sulfonate, sodium alkylnaphthalene sulfonate], and Acid salts, polyethylene glycol alkylaryl ether sulfate salts: cationic surfactants; alkylamines [e.g.
laurylamine, stearyltrimethylammonium chloride, alkylzmethylbenzylammonium chloride], polyoxyethylene alkylamines: nonionic surfactants; polyoxyethylene glycol esters [e.g., polyoxyethylene alkylaryl ether, and condensates thereof] , polyoxyethylene glycol esters [for example, polyoxine ethylene fatty acid ester], 45-polyhydric alcohol esters [for example, polyoxyethylene sorbitan monolaurate] - amphoteric surfactants, and the like.

Other stabilizers, fixing agents [e.g., agricultural soap, casein lime, sodium alginate, polyvinyl alcohol (
PVA), vinyl acetate adhesive, acrylic adhesive],
Efficacy extenders: Dispersion stabilizers (for example, casein, tora-kakanto, cal-xymethylcellulose (CAfC), polyvinyl alcohol (PVA)): Synergists can be mentioned.

The compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field.

Forms of preparations include emulsions, oils, wettable powders, aqueous solutions, suspensions, powders, granules, powders, and the like.

The herbicide of the present invention contains the active ingredient in an amount of about 0.001 to 100%.
% by weight, preferably from about 0.005 to about 95% by weight.

For actual use, the various preparations mentioned above are ready-to-use-prepara.
The active compound content in
~95% by weight, preferably about 0.05% to about 60% by weight
A range of is appropriate.

The content of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and weed growth status.

The compound of the present invention may further be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators, attractants [e.g. Organic phosphoric acid ester compounds, carbamate compounds, dithio(
or thiol) carbamate-based compounds, organic chlorine-based compounds, dinitro-based compounds, organic sulfur or metal-based compounds, antibiotics, diphenyl ether-based compounds, urea-based compounds, triazone-based compounds] or/manufactured fertilizers, etc. You can also do that.

Freeze or ready-to-use preparations containing the active ingredients of the present invention.
Application methods, spraying, spraying, spraying, misting, atomizing, etc., which are commonly used in the agricultural chemical manufacturing field.
tornizing), powder, powder, water surface application,
Boring (pourina)]: soil application, [
For example, soil contamination, 5 prinkli
? 1g)] etc. In addition, the so-called ultra-high concentration small amount spraying method (ml tra-tow-vo
lume). In this way it is possible to contain 100 grams of active ingredient.

The application rate per unit area is from about 0.1 to about 5.0% active compound per hectare. OKg, preferably about 0.2
~2.0 Kg can be used. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

According to the present invention, the compound of general formula (1) is included as an active ingredient, and a diluent (solvent and/or
II or carrier) and/or surfactant,
If necessary, the sail can be provided with a herbicidal composition containing, for example, stabilizers, fixing agents, synergists.

According to the present invention, weeds and/or their growth sites are treated with the compound of general formula (1) alone or in the presence of a diluent (solvent and/or filler or carrier).
and/or surfactants (stabilizers, if necessary)
A weed control method can be provided in which a fixing agent, synergist, etc. are mixed and applied.

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

49- Example 1 (hydrating powder) 1.15 parts of the compound of the present invention, a mixture of powdered diatomaceous earth and powdered clay (1:5), 80 parts, alkylbenzenesulfonic acid) IJum = 2gL alkylnaphthalenesulfone Three parts of sodium mortar formalin condensate were ground and mixed to make an irrigation agent. This is diluted with water and sprayed onto weeds and/or their growing areas.

Example 2 (emulsion) 2.30 parts of the compound of the present invention vlJA, key yvy, 55
4. Polyoxyethylene alkylphenyl ether.

8 parts, calcium alkylbenzenesulfonate.

7 parts were mixed and stirred to form an emulsion. Dilute this with water and
Spray weeds and/or their growing areas.

Example 3 (Powder) 43, 1.5 parts of the compound of the present invention, 5 parts of Ingrobil High 50-Dorodan Phosphate (PAP), 0, 98% of powdered clay were ground and mixed to make a powder, and a powder was prepared. /Or sprinkle powder on their growing areas.

Example 4 (granules) 4.4.10 parts of the compound of the present invention, bentonite (montmorillonite), ao61s, talc (talc), 58 parts,
Add 25 parts of water to a mixture of 2 parts of lignin sulfonate, knead well, and use an extrusion granulator to make 10~4
Dry at 40 to 50°C to form granules with a concentration of 0 mets/yu. Sprinkle this on weeds and/or their growing areas.

The observed effects of the active compounds of the present invention can be summarized from the following results.

Trial distribution example 1 Pre-emergence soil treatment test Preparation of active compound Carrier: Acetone 5 parts Emulsifier: Pensoloxypolyglycol edel 1 part Preparation of active compound The drug is 1 part active compound and the above amount. A carrier and an emulsifier are mixed to obtain an emulsion. The drug is prepared by diluting it with water to a predetermined size.

Test method: In a greenhouse, soybean seeds were sown in a 1000 cJ pot filled with field soil, and soil mixed with Aobifolia and Shiroza mulberry was poured on top to a depth of 1a.

One day after sowing and covering the soil, the above-mentioned preparation system g was uniformly spread on the soil surface layer of each test pot to a predetermined concentration. Four weeks after spraying, the herbicidal effect and the degree of chemical damage to crops VC were investigated.

Evaluation of weeding effect 10: Weed killing rate 100% (complete death) in the untreated area 9: Kill rate 90 or more and less than 100% in the untreated area 8
: 〃 80th person 〃 90% 〃7
: l/ 70% 〃 80chi
〃6: // 60% 〃7
Person in charge 0〃5: // 50%
〃 60% 〃4: // 4
0% 〃 50% 〃3: //
30% I/4Q Section 〃2: //
20% 〃 30chi 〃1:
// 10% 〃 20% 〃0:
〃 Less than 10% (no herbicidal effect) Evaluation of phytotoxicity 10 Phytotoxicity rate of 90% or more compared to untreated area (damage to several items) 9 〃 80% or more and less than 90% 8 〃 70% 〃80% 〃7
〃 60chi 770% 〃6
〃 50% 〃60% 〃5
〃 40% /150% 〃53-4 〃 30% 〃40 Section
〃3/l 20%//3
0% 〃2 〃 10% //
20% 〃l // o 10%
Less than 0% (no drug damage) Test results are shown in Table 1.

Table 1 Eaves: Compound products are the same as in the synthesis examples below and Tables 5 and 6.

54- Trial jd Example 2 Stem and leaf treatment test In a greenhouse, 2000-pots filled with field soil were
Sow soybean seeds and mix 11 tons of soil with Aobiyu and Shiroza seeds on top! It was covered with soil to a depth of r1 cm.

Ten days after sowing (in the early stages of leaf development for soybeans), a chemical solution prepared in the same manner as in Test Example 1 was uniformly sprayed onto the stems and leaves of the test plants in each test pot to a predetermined concentration.

Three weeks after spraying, the herbicidal effect and phytotoxicity of 5 liters were investigated in the same manner as Test Test 1. The test results are shown in Table 2.

Notes to Table 2 (fl) Compound composition is the same as in Synthesis Examples below and Tables 5.6 and 7.

(2) Comparative chloroxuron: 3-(4-(4-chlorophenox7)phenyl)-1,x-tumethylurea It was confirmed that the active compounds of the present invention other than those exemplified in the above test also exhibited excellent selective herbicidal effects. did.

Next, a synthesis example will be shown, and aniIJ of the general formula (IV) of the present invention will be described.
We will specifically describe the method for producing the ion derivative.

Synthesis Example 1 (Compound V-1) 4-Aminephenol 10.9F'5 Dissolved in 50I+Il of methyl sulfoxide, and added potassium carbonate 1 to this solution.
52 t is added and the contents are heated at 90° C. for 1 hour in a stream of desired gas. Then cool to 50°C, 2-chlorobenzothiazole 17. Of'550-60℃, then 70℃
Heat to ~80°C and react for 3 hours. After cooling to room temperature, the contents were poured into ice water, the separated oil was extracted with chloroform, the chloroform layer was thoroughly washed with water, and the chloroborm layer was distilled off to obtain the target product, 4-(2-benzothia). 20.69 of zolyloxy)aniline are obtained. ? 1261, 6 3 5 By almost the same method as above, as shown in Table 3 below,
An IJ derivative of the general formula (IV) of the present invention was prepared.

-5'3- Next, the method for producing the phenyl isocyanate derivative of the general formula (Vl) of the present invention will be specifically described.

Synthesis Example 2 (Kakugyomono Vl-1) 4-(2-Benzothiazolyloxy)aniline 24.2
1-) Dissolve in 150ml of toluene and dropwise add 30*lf of a toluene solution of 11.9f of trichloromethyl chloroformate at 5 to 1O<0>C over 1 hour while stirring. After dropping, gradually heat the mixture for 70 minutes until the generation of hydrogen chloride gas stops.
Heat to ~80°C. After the reaction is complete, toluene is distilled off under reduced pressure and the residue is left at room temperature to form the desired crystal 4.
-(2-Benzothiazolyloxy)phenylisocyanate 25,5f is obtained.

mp, 72-74°C 60- In almost the same method as above, as shown in Table 4 below,
A phenyl isocyanate derivative of the general formula (1) of the present invention was produced.

61- In the 61st generation, Yumei Moto's activation combination power is your heart - 1 to 1 of the silver formula (1)
%Phenylurea J conductor manufacturing method k will be specifically described.

Synthesis Example 3 (Compound AI) 1.1-methyl-3-(4-hydroxyphenyl)urea tsr'1-methylformamide 80IRI VC
Then, 14.5 minutes of anhydrous potassium carbonate was added to this solution, and the mixture was heated at 85 to 90° C. for 1 hour in a nitrogen gas stream. Shun, who slightly VC'd the contents at t-50℃, 2.4.5
-) Dichlorteazole 1 & 9f ligation. After adding the mixture dropwise, stir gently at 55-60°C for 2 hours. After cooling to 4℃, pour Uchiya Nazu into ice water and dry the precipitated crystals in an oven to obtain the target product 63-1,1-tmethyl-3-(:4-(4,5-dichloro-
2-thiazolyloxy)phenyl]urea 26.92 is served. ? ? 171.159-162℃ Above Synthesis Example 3
Substituted phenylurea derivatives obtained by using almost the same method as above are shown in Table 5 below.

64- Note (1) In the table, the bonding position indicates the bonding position of the ureido group (OC1i, )\ to the phenyl side, "p" indicates the zora position, and "脩" indicates the meta position, respectively.

(2) In the table, for example, compound &2 represents the following formula.

(1-Methyl-1-methoxy-3-[4-(2-benzothiazolyloxy)phenyl]urea) Synthesis example 4 (Compound No Aj) 3-(2-benzothiazolyloxy)aniline 24,2
f, triethylamine 11.12 to toluene 120
ml, and at 30-35°C add 30-30ml of a toluene solution of 11.8f of trimethylcarbamoyl chloride. Thereafter, the contents were reacted at 40 to 55°C for 4 hours, cooled, and the toluene layer was dissolved in 1% aqueous hydrochloric acid solution and 1% water hydrated.
Wash sequentially with IJum aqueous solution and water. Toluene was distilled off under reduced pressure, and the entire residue was washed with a small amount of methanol to obtain the target product, 1.1-tmethyl-3-(3-(2
-Benzothiazolyloxy)phenyl]urea 17.5
t is obtained. ? yIp, 158-160°C The fLf-substituted phenylurea derivatives produced by substantially the same method as in Synthesis Example 4 above are shown in Table 6 below.

67- 68- Synthesis Example 5 0 (Compound 10) 26.81 of 4-(2-benzothiazolyloxy) phenyl isocyanate was dissolved in 80 l of toluene, and 40 g of trimethylamine was added to the solution while stirring well at both temperatures. Add 12.4 f of aqueous solution and stir for an additional hour. Precipitated Ll
When you encounter a mostly colorless crystal IF, the object 1, 1-
trimethyl-3-(4-(2-benzothiazolyloxy)
Phenyl]urea 2852 is obtained. mp, 15
The tt-substituted phenylurea derivatives produced at 4 to 155° C. in substantially the same manner as in Synthesis Example 5 are shown in Table 7 below.

Claims (1)

[Claims] 1. General formula: In the formula, X and Y each represent a -logon atom, and together with the heterocycle to which they are bonded, X and Y represent benzo- A fused heterocycle can be formed entirely, where:
The benzo-fused heterocycle is formed by at least one member selected from the group consisting of a rhodane atom and a lower alkoxy group.
, A and B each represent an oxygen atom or a sulfur atom, and R represents a methyl group or a methoxy group, which may be substituted. 2. The substituted phenylurea derivative according to claim 1, which is bonded to the z-ra position. 1 Formula: 1.1-dimethyl-3-(4-(4,s-cyclo-2-thiazolyloxy)phenyltourea) according to claim 1, represented by the formula: 44 Formula: 1.1 described in Scope No. 1
. -Tmethyl-3-(4-(2-benzothiazolyloxy)phenyl iorea. 5. General formula: In the formula, X and Y each represent a halogen atom, and
and Y together with the heterocycle to which they are bonded can form a benzo-fused heterocycle, where the benzo-fused ring is at least one member selected from the group consisting of a halogen atom and a lower alkoxy group. A is an oxygen atom, Hαl is a halogen atom, and a compound represented by the general formula: where B represents an oxygen atom or a sulfur atom. R represents a methyl group or a methoxy group, and M represents a hydrogen atom or an alkali gold 17-4 atom. A method for producing a substituted phenylurea derivative, wherein B and R are the same as above. 6. General formula: In the formula, X and yit each represent a rhodane atom, and XIY can be combined with the heterocycle to which they are bonded to form a benzo-fused heterocycle. , wherein the benzo-fused heterocycle is at least -gvcx selected from the group consisting of -.rodane atoms and lower alkoxy groups.
A and B each represent an oxygen atom or a sulfur atom, which may be substituted by 5- A method for producing an ft-substituted phenyl urea derivative represented by the general formula: where X, Y, A, B and R are the same as above. 7. General formula: In the formula, X and Y each represent a halogen atom, and
(!l: Y can be taken together with the heterocycle to which they are attached to form a benzo-fused heterocycle, where the benzo-fused heterocycle consists of a halogen atom and a lower alkoxy group. By at least one glue selected from the group.
6-A and B, which may be substituted, each represent a sulfur atom as an acid atom, and a compound represented by the general formula: where R is a methyl group or a methoxy group, and A method for producing an f#-substituted phenylurea derivative represented by the general formula: wherein X, Y, A, B and R are the same as above. 8. General formula: In the formula, X and Y each represent a rhodan atom, and together with the heterocycle to which they are bonded, X and Y form a benzo-fused complex atom. can be done here,
The benzo-fused complex may be substituted with at least one member selected from the group consisting of a lozenge atom and a lower alkoxy group, A and B each represent a sulfur atom or a sulfur atom, R A herbicide characterized by containing as an active ingredient a substituted phenylurea derivative represented by: methyl group or methoxy group. 9. General formula: In the formula, X and Y each represent a rhodane atom, and together with the heterocycle to which they are bonded, X and Y form a benzo-fused heterocycle. can be done here,
The benzo-fused heterocycle may be substituted with at least one member selected from the group consisting of a rhodane atom and a lower alkoxy group, and A and B each represent an oxygen atom or a sulfur atom. Aniline derivative represented by 10. The aniline derivative according to claim 9, wherein the amino group (-NH!) is bonded to the methano-position. 11. General formula: In the formula, X and Y each represent a halodane atom, and
and Y together with the heterocycle to which they are attached can form a benzo-fused heterocycle, where the pen'zo-fused ring is a halodane atom and the lower alkoxy A is an oxygen atom or a sulfur atom. A compound represented by: where Hαt represents a rhodan atom. In the formula, B represents an oxygen atom or a sulfur atom, and M represents a hydrogen atom or an alkali metal atom. A method for producing an aniline derivative represented by the formula, where X, Y, A and Bit are the same as above. 1z General formula: In the formula, X and Y each represent a rodan atom, and X and Y together with the heterocycle to which they are bonded form a benzo-fused heterocycle. can be done, where:
The benzo-fused heterocycle may be substituted with at least one member selected from the group consisting of a rhodane atom and a lower alkoxy group, and A and B each represent an oxygen atom or a sulfur atom. Phenyl isocyanate derivative. 13. The phenyliso7anate derivative according to claim 12, wherein the isocyanato group (-N, , C=0) is bonded to the meta- or vara-position. 14. General formula; In the formula, X and Y each represent a halodane atom, and
and Y together with the heterocycle to which they are attached,
A and B may form a benzo-fused heterocycle, where the benzo-fused heterocycle may be substituted with at least one type of V selected from the group consisting of a halocarbon atom and a lower alkoxy group, and A and B are The general formula is: where X, Y, A and B are the same as above A method for producing a phenylinocyanate derivative represented by .