JPS6045572A - Sulfonylurea derivative, its preparation and selective herbicide containing said derivative - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [A and B are H, lower alkyl, halogen, COOR (R is H or lower alkyl, CONR1R2 (R1 and R2 are R), etc.; W is S or NR8 (R8 is R or phenyl); X and Y are R, lower alkoxy, halogen, lower alkoxyalkyl, etc.; Z is N or CH]. EXAMPLE:N-[ ( 4-Methoxy-6-methylpyrimidin-2-y1 )aminocarbonyl ]-4-chlorothiazole-5-sulfonamide. USE:A selective herbicide. It exhibits strong herbicidal activity to various weeds, and has high safety to rice, wheat and corn. Since the compound exhibits high herbicidal activity at an extremely low dose, it is useful also as the herbicide for orchard, uncultivated land, etc. PREPARATION:The compound of formula I can be prepared e.g. by reacting the pyrazolesulfonyl isocyanate derivative of formula II with aminopyrimidine or aminotriazine derivative of formula III in an inert solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel sulfonylurea derivative, a process for producing the compound, and a selective herbicide containing the compound as an active ingredient.

JP-A-55-102577 and JP-A-561394
No. 66 describes that pyridine sulfonylurea derivatives are useful as herbicides, and JP-A-56-169688 describes that virolsulfonylurea derivatives are useful as herbicides.

It is essential to use herbicides to protect important crops such as rice, wheat, and corn from weed damage and increase yields. Particularly in recent years, in arable land where these useful crops and weeds coexist, there has been a demand for selective herbicides that can selectively kill only weeds without causing chemical damage to crops even when applied to the foliage of crops and weeds simultaneously. It is rare. In addition, environmental pollution prevention,
From the perspective of reducing economic costs during transportation and spraying, search research has been carried out for many years to find compounds that achieve high herbicidal effects with as low a dose as possible. Although some compounds with these properties are currently used as selective herbicides, there is still a need for new compounds with these properties.

In order to develop herbicides that are selective for important crops, the present inventors have spent many years researching many compounds in order to produce compounds with higher herbicidal power and higher selectivity. We have studied its herbicidal properties. As a result, the compound of the present invention represented by the general formula (1) is effective against many weeds in both soil treatment and grass foliage treatment, compared to known pyridine sulfonylurea derivatives and virol sulfonylurea derivatives. The present invention was completed after discovering that it has extremely strong herbicidal power and is highly safe for important crops such as rice, wheat, and corn. On the other hand, since the compound of the present invention exhibits high herbicidal activity at a much lower dose than conventional herbicides, it is also useful as a herbicide for other orchards and non-cultivated land.

The compound of the present invention represented by general formula (1) is a new compound, and can be easily produced by selecting any one of Reaction Formulas 1 to 3 below.

(I) [In the formula ^, TI, u, y, , l and 2 have the same meanings as above. ] That is, the sulfonylisocyanate derivative is dissolved in a sufficiently dried inert solvent such as dioxane or acetonitrile, and the pyrimidine or triazine derivative represented by formula 1) is added to the solution and stirred, generally, the sulfonylisocyanate derivative is quickly dissolved. The reaction yields the compound (I) of the present invention. If the reaction is difficult to proceed, the reaction can be facilitated by adding a small amount of a base such as triethylamine, triethylenediamine, pyridine, sodium alkoxide, sodium hydride, etc.

Anti-empress N) [In the formula, A, , B, W, X, Y and Z have the same meanings as above. R represents alkyl n;m or a phenyl group.

] That is, the sulbonamide derivative (V) is mixed with acetone,
Compound (TV) is obtained by reacting with chloroformic acid ester or carbonic acid ester in a solvent such as methyl ethyl ketone in the presence of a base such as potassium carbonate, and after the reaction, treating with an acidic substance such as hydrochloric acid. The compound (TII) of the present invention is then heated with the compound (TII) in a solvent such as 1 to toluene.
) can be obtained.

(■) (■) [In the formula, A, B and Mi have the same meanings as above.

E and F are halogen atoms, R2 is a lower alkyl group,
G represents a nitrogen atom or a -CI+- group. ]] A compound (■) which is a part of the compounds of the present invention is synthesized by reacting the sulfonamide derivative (V) with pyrimidine or triazine isocyanate (■) with reference to JP-A-56-154471, Next, by reacting with sodium alcoholade, compound (■), which is also a part of the compounds of the present invention, can be synthesized. A part of the raw material sulfonyl isocyanate used in Reaction Formula 1 is synthesized by synthesizing thiazole or imidazole sulfonamide with reference to U.S. Pat. It can be synthesized by referring to.

Many of the intermediate sulfonamides are new compounds, and they can be synthesized by appropriately selecting several synthetic routes 1 to 1 described below.

-The following margins- [In the formula, A, B, W, 1. Y and Z have the same meanings as above. ] Specific examples of the compounds of the present invention are shown in Tables 1 and 2, but the present invention is not limited thereto.

Compound teeth are referred to in the description below.

Table 1 Me: Methyl group Et: Ethyl group Pr: Propyl group B
u Nibutyl group Ph: Indicates a phenyl group.

Examples of the synthesis of intermediate sulfonamides used in the present invention are described below as reference examples.

Reference Synthesis of 4-Chlorthiazole-5-sulfonamide 18 g of 4-chlorothiazole was slowly added to 50 ml of chilled chlorsulfonic acid at -10 to 0°C, and the mixture was heated at 120 to 125°C for 30 minutes, and then heated at 160 to 125°C for 30 minutes. 165°
The reaction was carried out at C for 8 hours. Thereafter, the mixture was cooled to 80° C., 40 ml of thionyl chloride was added, and the mixture was refluxed for 6 hours. After the reaction, the reaction mixture was cooled to room temperature, poured into water, and extracted with chloroform. The chloroborum layer was washed with water, dried and concentrated under pressure. Add 75ml of tetrahydrofuran to the residue and -
40 ml of concentrated ammonia water was added at 5°C. This was concentrated under reduced pressure, and the precipitated crystals were filtered, washed with water, and dried to obtain 17.2 g of 4-chlorothiazole-5-sulfonamide. Melting point: 167-168°C.Synthesis of 2-methylthiazole-5-sulfonamide Obtained from 2-methylthiazole according to Reference Example 1 above.

Melting point 159-160℃ Reference Synthesis of 4-methylthiazole-5-sulfonamide Obtained from 4-methylthiazole according to Reference Example 1 above.

Melting point 141-144°C Dojichi's row j Synthesis of 5-chloro-2-methylthiazole-4-sulfonamide 2-methyl-5-chlorothiazole 13. 4 g was added dropwise. After heating under reflux for 10 hours, sulfuric anhydride was distilled off, 31 g of thionyl chloride was added to the residue, and the mixture was heated at 100°C for 4 hours. After the reaction, the reaction solution was poured into ice water and extracted with ether. After distilling off the ether, 10 ml of tetrahydrofuran was added to the residue, which was dropped into 50 ml of concentrated aqueous ammonia (28%) at 10° C. or lower. This was concentrated under reduced pressure, and the precipitated solid was filtered, washed with water, and dried to give 5-chloro-2-methylthiazole-
2 g of 4-sulfonamide was obtained.

Melting point: 154-155°C Moxibustion lambda 5-methoxycarbonyl-2-methylthiazole-4-
Synthesis of sulponamide A solution of 3.5 g of sodium nitrite was added to a mixed solution of 8.6 g of 4-amino-5methoxycarbonyl-2-methylthiazole, 17.5 ml of concentrated hydrochloric acid, 5 ml of phosphoric acid, and 5 ml of acetic acid at -10°C to 0°C. The solution added at step 1 was stirred at -5° C. for 30 minutes, and then cuprous chloride was added in small portions. Og
In 70 ml of sulfur dioxide gas saturated acetic acid solution containing = 1O~
It was added dropwise at -5°C. After the dropwise addition, the mixture was stirred at 0 to 5°C for 4 hours, then poured into ice water and extracted with ether. The extract was thoroughly washed with water and saturated aqueous sodium bicarbonate, dried, and the solvent was distilled off to obtain crude sulfonyl chloride. The sulfonyl chloride obtained here was dissolved in 5 ml of tetrahydrofuran and added to 12.5 ml of 28% aqueous ammonia under water cooling at a temperature of 10°C or less. After stirring at room temperature for 3 hours, the solid obtained by concentrating under reduced pressure was filtered, washed with water and ether, and dried to obtain 4.9 g of the desired product.

Melting point: 128-134℃ 4-ethoxycarbonyl-2-methylthiazole-5-
Synthesis of sulbonamide Sulfonamide was obtained from 5-amino-4-ethoxycarbonyl-2-methylthiazole according to Reference Example 5 above.

Melting point: 135-137°C Medicine suggestion 1 Synthesis of 1-methylimidazole-4-sulfonamide Add N-methyl 4 to 100 ml of chilled chlorosulfonic acid.
, 25 g of midazole was slowly added at -10 to 0°C, and the mixture was reacted at 120 to 130°C for 18 hours. Then, cool to 80°C, add 40ml of thionyl chloride,
It was run at high speed for 3 hours. After the reaction, the reaction solution was cooled to room salt, poured into water, and extracted with chloroform. The chloroform layer was washed with water, dried and concentrated under shallow pressure. Thereafter, 13 g of the target product was obtained by treating the ammonia water in the same manner as in Reference Example 1.

Melting point: 222-225°C Gai Sani 1 Synthesis of 1,4-dimethylimidazole-5-sulfonamide Synthesis was performed from 1,4-dimethylimidazole according to Reference Example 7. Melting point: 184-186℃
-Synthesis of sulfonamide 1.1 g of 4-ethoxycarbonyl-5-mercapto-2-methylimidazole was dissolved in 30 ml of 85% acetic acid, and 1.5 g of chlorine gas was blown into the solution at 5-6°C. After the reaction, it was added to 20 ml of water and extracted with ether. After the ether was distilled off under reduced pressure, it was added to 30 ml of liquid ammonia. After distilling off the ammonia gas, 5 ml of water was added and the resulting solid was filtered off to obtain 0.75 g of the target product. Melting point: 189-194°C Specific synthesis examples of the compounds of the present invention will be described below using the sulfonamides obtained in Reference Examples 1 to 9, but the present invention is not limited thereto.

N-((4-methoxy-6-methylpyrimidin-2-yl)aminocarbonylgo 4-chlorothiazole-5-
Synthesis of sulfonamide (Compound No. 31) 9.9 g of the sulfonamide obtained in Reference Example 1 was dissolved in 100 ml of acetone, and 13.8 g of anhydrous potassium carbonate, n
5.2 g of -butyl isocyanate was added, the mixture was reacted at room temperature for 1 hour, and then refluxed for 3 hours.

After the reaction, the solvent was removed under reduced pressure, and the residue was dissolved in water and filtered. The filtrate was precipitated with dilute hydrochloric acid, filtered, washed with water, and dried to obtain 12.8 g of N-(n-butylaminocarbonyl)-4-chlorothiazole-5-sulfonamide. Melting point: 148-149°C To 6.0g of the above compound was added 100ml of dehydrated orthodichlorhenzene, and the temperature was 130-149°C.
Approximately 12 g of phosgene was bubbled in over 2 hours at . Thereafter, it was heated for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. Take 1.4 g from this residue and preliminarily add 2-amino-
0.7 g of 4-methoxy-6-methylpyrimidine was heated and melted in 30 ml of acetonitrile and added at room temperature.
Stirred for 8 hours. The precipitated crystals were filtered, washed with acetonitrile, and dried to obtain the target product N-((4-methoxyl 6-
Methylpyrimidin-2-yl)aminocarbonyl go 4
-0.9 g of chlorothiazole-5-sulfonamide was obtained. Melting point: 159-161 °C Synthesis of N-1(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-methyl-5-chloroimidazole-4-sulfonamide (Compound No. 207 ) 1-Methyl- obtained by sulfonating and amidating 1-methyl-5=chloroimidazole in the same manner as in Reference Example 7.8.
5-Chlorimidazole-4-sulbonamide (melting point 1
92-195℃) 10g and anhydrous potassium carbonate 18.3g
, 6.3 g of methyl chlorocarbonate was added dropwise to a mixed solution of 400 ml of dehydrated acetone at room temperature. After stirring at room temperature for 1 hour,
Heat to reflux for 15 hours. The reaction mixture was concentrated under reduced pressure, dissolved in water, and then filtered to remove insoluble matter. The filtrate was made acidic with dilute hydrochloric acid, and the precipitated crystals were filtered, washed with water, and dried to give N-(methoxycarbonyl)-1-methyl-5-chloroimidazole-4-.
9.0 g of sulfonamide was obtained. Melting point 175-178℃
A mixed solution of 2.0 g of the above compound, 0.97 g of 2-amino-4,6-dimethylpyrimicin, and 100 ml of dehydrated xylene was heated under reflux for 5 hours. After the reaction, it was concentrated under reduced pressure, and the precipitated crystals were filtered, washed with a small amount of acetonitrile, and dried to obtain the desired N-((4,6-dimethylpyrimidine-2-
1.6 g of 1-methyl-5-chloroimidazole-4-sulbonamide was obtained. Melting point: 208-210"c Next, according to Example 1.2 above, the compound specifically synthesized was synthesized in Example 1.2 together with the compound synthesized in Example 1.2 (compound omitted, 31,207), as well as the following third compound.
Shown in the table.

Table 3 When applying the compounds of the present invention as herbicides, a suitable carrier is generally used, such as a solid carrier such as clay, talc, bentonite, or diatom, or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons, etc. It can be used in combination with liquid carriers such as esters (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), and acid amides (dimethylformamide, etc.). If desired, emulsifiers, dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, etc. can be added, and the product can be put to practical use in any dosage form such as liquid, emulsion, wettable powder, powder, or granule. I can do it.

Next, examples of formulations of herbicides containing the compound of the present invention as an active ingredient will be shown, but the invention is not limited thereto.

In addition, in the following formulation examples, "parts" mean parts by weight.

However, Masudo Wettable powder Compound of the present invention Positive 2-----------50
Part Sieglite A ---1---------・-----
46 parts (Kaolin clay: Sieglite Industries ■Product name) Tsurupol 5039 ・−・−・−−−−−−−−−
2 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical A11 part name) Carplex (anti-caking agent) ----- 2 parts (white carbon: Shionogi & Co., Ltd. (■Product name) ) The above is mixed and pulverized uniformly to make a hydrating agent.When using, mix the above hydrating agent with 5
Dilute it 0 to 50,000 times and spray it so that the amount of active ingredient is 0.005 kg to 10 +r per hectare.

5B1 Example D Hydrating agent Compound of the present invention Positive 76--------------------- 7
Part 5 Sieglite A -1---------・------
--19 parts (kaolin clay: Zeeklite Kogyo ■trade name) Tsurupol 5039 ---1 ---2 parts (combination of nonionic surfactant and anionic surfactant) Mixture; Toho Chemical (trade name) Carplex (anti-caking agent) ----- 4 parts or more (white carbon: Shionogi & Co., Ltd. (11 brand name)) are uniformly mixed and pulverized to make a wettable powder.

Loss example 1 Wettable powder Compound of the present invention No. 155-------50
Part Sieglite A ----------------46
(Kaolin clay: Sieglite Kogyo Sumikiku product name)
Tsurupol 5039 -, -----・-------2 parts (
Mixture of nonionic surfactant and anionic surfactant: Toho Chemical G'XI (trade name) Carplex (anti-caking agent)---2 parts (white carbon: Shionogi &Co.'s trade name) or more Mix and grind uniformly to make a wettable powder.

Chikki Mawari ↓ Wettable powder Compound of the present invention NO, 1B 2----------------------2
Part 5 Theta Light A ----------------
------- 11 parts (Kaolin clay: Zikrite Industries (■Product name) Tsurupol 5039 -1---
-------2 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical (■Product name) Carplex (anti-caking agent) ----2 parts (White Carbon : Shionogi & Co., Ltd. (trade name) The above ingredients are uniformly mixed and pulverized to make a wettable powder.

Emulsion Compound of the Invention No. 17--
−−−2 part oxygen −−−−−−−−−−−−
---------- 78 parts dimethylformamide ---
---, 15 parts Tsurupol 2680 ---------
5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical o11 part name) The above is mixed uniformly to form an emulsion. When used, the above emulsion is diluted 10 to 10,000 times and spread at an amount of 0.005 kg to 10 active ingredients per hectare.

Circulation box 1 Flowable compound of the present invention It, 183-------2
5 parts Agelisil S-710---10 parts (Nonionic surfactant: Kao Atlas ■Product name) Lunosox 1000 C------0, 5 parts (
Anionic surfactant: Toho Chemical ■Product name) 1% Rhodopol water ---------- 1-20 parts (Thickener: Lone Boulin Co., Ltd. product name) Water ------- −−−1〜−−−−=−−−−−−−−−−−−−−−−44
, 5 parts or more are uniformly mixed to form a flowable agent.

y-touchi granules Compound of the present invention No. 31------------
--- 0.5 part hentonite ---
--55,0 parts talc ---
After uniformly mixing and pulverizing 44.5 parts or more, a small amount of water is added, the mixture is stirred and kneaded, the granules are enlarged using an extrusion type granulator, and the granules are dried to form granules.

Compound of the present invention Granules Part 156 ---------- 0.7 parts bentonite ------- 55.0 parts talc ------- ---After uniformly mixing and pulverizing 44.3 parts or more, a small amount of water is added and the mixture is stirred and kneaded, granulated using an extrusion granulator, and dried to form granules.

Furthermore, the compound of the present invention may be applied in combination with other herbicides, various insecticides, fungicides, synergists, etc. when preparing or spraying, if necessary.

Other types of herbicides mentioned above include, for example, Farm Chemicals Handbook.
llandbook), 68th edition (1982).

The compound of the present invention can be applied to control various weeds in agricultural and horticultural areas such as fields, paddy fields, and orchards, as well as in non-agricultural areas such as playgrounds, vacant lots, and railway edges, and the amount of the applied drug depends on the application situation. Although there are differences depending on the application period, application method, target grass species, cultivated crops, etc., the appropriate amount of active ingredient is generally about 0.005 to 10 kg per hectare.

Next, the usefulness of the compounds of the present invention as herbicides will be specifically explained in the following test examples.

i1 Top Weeding effect test by soil treatment Sterilized diluvial soil was placed in a dark blue plastic box measuring 15 cm wide, 22 cm wide, and 6 cm deep, and rice, Japanese wild grass, Japanese grasshopper, Cyperus japonica, Koakaza, Portulaca purslane, Cucophyllacea japonica, and Japanese dogwood were mixedly sown. After covering the soil to a depth of approximately 1.5 cm, the soil surface was uniformly dispersed so that the amount of active ingredient was at a predetermined ratio.

The chemical solution used for spraying was the wettable powder of the formulation example described above diluted with water and sprayed over the entire surface with a small sprayer. Four weeks after spraying the chemical solution, the herbicidal effect on rice and various weeds was investigated according to the following criteria G.

The results are shown in Table 4.

Some of the compounds of the invention have selectivity for certain crop species.

Judgment Criteria 5- Weed killing rate 90% or more (almost complete death) 4-
Weed killing rate 70-90% 3- Weed killing rate 40-70% 2- Weed killing rate 20-40% 1- Weed killing rate 5-20% 〇 - Weed killing rate 5% or less (almost ineffective) However, the above killing rate The grass rate was determined by measuring the weight of above-ground grass in the chemically treated area and the weight of above-ground grass in the non-treated area using the following formula.

11 Garden 21 Weeding effect test by stem and leaf treatment 15cm long,
Sterilized diluvial soil was placed in a plastic box measuring 22 cm wide and 6 cm deep, and seeds of rice, crabgrass, cyperus, cyperus japonica, leaf lily, dogberry, corn, soybean, wheat, and tomato were sown in rows and rows, respectively. 1.5cmfEt soil. When each plant reached the 2-3 leaf stage, the active ingredient was uniformly sprayed onto the stems and leaves so that the amount of the active ingredient was at a predetermined ratio.

The chemical solution used for spraying was the hydrating agent of the formulation example described above diluted with water and sprayed over the entire surface of the stems and leaves of various weeds using a small sprayer. Four weeks after spraying the chemical solution, the herbicidal effect on rice and various weeds was investigated according to the criteria of Test Example-1.

The results are shown in Table 5.

Margin below Table 4 Margin below Table 5

Claims (4)

[Claims] (1) General formula (I): [In the formula, ^ and B are each independently a hydrogen atom, a lower alkyl group, a halogen atom, COOR (R represents a hydrogen atom or a lower alkyl group) CONR+ Rx (11+
, R2 each independently represent a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, n represents an integer of Oll or 2), 0R4 (Ra represents a hydrogen atom or a lower alkyl group), nitro group, NR5RB (R5R8 each represents (Independently represents a hydrogen atom or a lower alkyl group.)
, NlIC0Rt7 (Rヮ represents a lower alkyl group.)
Alternatively, it represents a phenyl group which may be substituted with a lower alkyl group, a halogen atom, or a nitro group. W is a sulfur atom or NRg (represents an Rg hydrogen atom, a lower alkyl group, or a phenyl group). ? , R
,. (R, R,. Each independently represents a hydrogen atom or a lower alkyl group.) or O'CIIR,, -COOR,l(R,,
R. each independently represents a hydrogen atom or a lower alkyl group. ) group, and 2 represents a nitrogen atom or a CI+ group. ] A sulfonylurea derivative represented by (2) General formula (■): [In the formula, ^ and B each independently represent a hydrogen atom, a lower alkyl group, a halogen atom, COOR (R represents a hydrogen atom or a lower alkyl group) CONR+ R2 (Rt,
R2 each independently represents a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, and n represents an integer of 0, ■ or 2), 0Ra (R4 represents a hydrogen atom or a lower alkyl group), nitro group, NR51? . (R5Re each independently represents a hydrogen atom or a lower alkyl group), NlICORヮ (R represents a lower alkyl group) or a lower alkyl group, a halogen atom,
Indicates a phenyl group which may be substituted with any nitro group. Disease indicates a sulfur atom or NR, (R indicates a hydrogen atom, a lower alkyl group, or a phenyl group). [In the formula, X and Y are each independently a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkoxyalkyl group, NR, lR1, (++9R,, each independently represents a hydrogen atom or a lower alkyl group) or 0CIIR,, -COOR,, (R,, R,
- Each independently represents a hydrogen atom or a lower alkyl group. ) group, and Z represents a nitrogen atom or a CI+ group. ] General formula (I) characterized by reacting an aminopyrimidine or aminotriazine derivative represented by the following in an inert solvent: [wherein A and B each independently represent a hydrogen atom, a lower alkyl group, Halogen atom, C0OR (+1 indicates a hydrogen atom or lower alkyl group) CONJ R2 (R1, R
2 each independently represents a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, and n represents an integer of 0, 1 or 2.)
, 0R4 (174 represents a hydrogen atom or a lower alkyl group), nitro group, NR5Re (R5R8 each independently represents a hydrogen atom or a lower alkyl group), N
lCOR? , (Rヮ represents a lower alkyl group) or a phenyl group optionally substituted with a lower alkyl group, a halogen atom, or a nitro group. The number is a sulfur atom or N Rt (R represents a hydrogen atom, a lower alkyl group or a phenyl group.) X and Y are each independently,
Hydrogen atom, lower alkyl group, lower alkoxy group, halogen atom, lower alkoxyalkyl group, NRq R111
(R4'tb each independently represents a hydrogen atom or a lower alkyl group.) or OCHR,, -COORlz
(R,,R,. Each independently represents a hydrogen atom or a lower alkyl group.) group, and Z represents a nitrogen atom or a CI group. ] A method for producing a sulfonylurea derivative represented by (3) The following formula (■): [In the formula, A and B are each independently a hydrogen atom, a lower alkyl group, a halogen atom, C00II (R represents a hydrogen atom or a lower alkyl group.) CONR+ R2 (R
t and R2 each independently represent a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, n represents an integer of 0, 1 or 2), 0R4 (R4 represents a hydrogen atom or a lower alkyl group), nitro group, NR5R6 (R5R , each independently represents a hydrogen atom or a lower alkyl group.)
, NlICOR, (R represents a lower alkyl group) or a phenyl group optionally substituted with a lower alkyl group, a halogen atom, or a nitro group. K represents a sulfur atom or NR, (R represents a hydrogen atom, a lower alkyl group, or a phenyl group). R1 represents an alkyl group or a phenyl group. ] and the following formula (■): [In the formula, X and Y are each independently a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkoxyalkyl group, Nl ? 41R5° (R?RI6 each independently represents a hydrogen atom or a lower alkyl group) or OC1111,, -COOR,,'(R,,
Each R independently represents a hydrogen atom, I≧ or a lower alkyl group. ) group, and Z represents a nitrogen atom or a C11 group. ] General formula (I) characterized by reacting an aminopyrimidine or aminotriazine derivative represented by the following in an inert solvent: [In the formula, A and B each independently represent a hydrogen atom, a lower alkyl group, Halogen atom, C00I? (R represents a hydrogen atom or a lower alkyl group.) CONR+ R2 (Ra
lR2 each independently represents a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, n represents an integer of 0.1 or 2), 0R4 (Ra represents a hydrogen atom or a lower alkyl group), nitro group, NR5Re (Rs (Re each independently represents a hydrogen atom or a lower alkyl group.)
, NlIC0R9 (11 indicates a lower alkyl group) or a phenyl group which may be substituted with any of a lower alkyl group, a halogen atom, or a 20 group. - represents a sulfur atom or NR, (R represents a hydrogen atom, a lower alkyl group, or a phenyl group.) X and Y each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group,
Halogen atom, lower alkoxyalkyl group, NR, R,
0 (R, R, 0 each independently represent a hydrogen atom or a lower alkyl group) or QC) IR,, -GOOR
, (R, , R, 2 each independently represents a hydrogen atom or a lower alkyl group) group, and 2 represents a nitrogen atom or CI (represents a group). A method for producing a sulfonylurea derivative. (4) General formula (I): [In the formula, ^ and B are each independently a hydrogen atom, a lower alkyl group, a halogen atom, COOR (R represents a hydrogen atom or a lower alkyl group, ,) CONRIR2 (Ra I
R2 each independently represents a hydrogen atom or a lower alkyl group. ), 5OnR3 (R3 represents a hydrogen atom or a lower alkyl group, n represents an integer of 0, 1 or 2), 0R4 (R4 represents a hydrogen atom or a lower alkyl group), nitro group, NR5RG (R511 , each independently represents a hydrogen atom or a lower alkyl group.)
NlICOR, (11 represents a lower alkyl group) or a phenyl group optionally substituted with a lower alkyl group, a halogen atom, or a nitro group. - represents a sulfur atom or NR, (R represents a hydrogen atom, a lower alkyl group, or a phenyl group) ,NRQ RID
(Ral Rr. each independently represents a hydrogen atom or a lower alkyl group.) or 0CIIR-COOR(RRRO 1)L
11 1L each independently represents a hydrogen atom or a lower alkyl group. ) group, and 2 represents a nitrogen atom or a C11 group. ] A selective herbicide characterized by containing one or more sulfonylurea derivatives represented by the following as an active ingredient.