JPS59219281A - Pyrazolesulfonylurea derivative, its preparation and selective herbicide containing it - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [A is H, lower alkyl, or phenyl; B is H, or lower alkyl; D is H, COOR(R is lower alkyl), COAr(Ar is phenyl which can be replaced with halogen), etc,; X and Y are H, lower alkyl, etc.; Z is N, etc.]. EXAMPLE:N-[(4, 6 - Dimethyoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl)- 1-methylpyrazole-5-sulfonamide. USE:A selective herbicide. Having high herbicidal action and high safety to important crops such as rice plant, wheat, etc. Since a small amount of it is effective, it is also usedful as a herbicide for orchards, or nonagricultural lands. PREPARATION:A derivative shown by the formula II is dissolved in a sufficiently dried inert soluvent such as dioxane, etc. and a pyrimidine or triazine derivative shown by the formula III, to give a compound shown by the formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel pyrazolesulfonylurea 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-56-139
No. 466 f'H describes that pyri-synsulfonylurea derivatives are useful as herbicides, and JP-A-56-169988 describes that pyrrolesulfonylurea derivatives are useful as herbicides.

On the other hand, conventional pyrazole derivatives are described, for example, in Japanese Patent Publication Nos. 54-36648, 41872-1972, 2276-1976, 58670-1987, and 133265-1980. It is known that compounds such as these 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 producing a postcard on 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.

The above-mentioned pyridine sulfonylurea derivatives and pyrrolesulfonylurea derivatives exhibit superior herbicidal effects at lower doses than conventional herbicides, but do not exhibit selectivity for useful crops. Furthermore, although some of the pyrazole derivatives known so far have shown selectivity for rice, they require relatively high dosages and cannot necessarily be said to have satisfactory properties.

The present inventors have continued research over many years in order to develop pesticides that are selective for important crops. We have investigated its herbicidal properties. As a result, the compound of the present invention represented by the general formula (1) is significantly effective against many weeds in both soil treatment and foliage treatment, compared to known pyridine sulfonylurea derivatives and pyrrolesulfonylurea derivatives. The present invention was completed after discovering that it has 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 desired compound, and can be easily produced by selecting any one of Reaction Formulas 1 to 3 below.

(1) [In the formula, Δ, B, , D, , X, Y and Z have the same meanings as above. ] That is, 1. Generally, a pyrazole sulfonyl isocyanate derivative is dissolved in a sufficiently dried inert solvent such as dioxane or acetonitrile, and a pyrimidine or triazine derivative represented by formula (Ill) is added thereto and stirred each time. Compound (1) of the present invention by reacting with
is obtained. If the reaction is difficult to proceed, use an appropriate base,
For example, the reaction can easily proceed by adding a small amount of triethylamine, triethylenediamine, pyridine, sodium alkoxide, sodium hydride, or the like.

Anti-Map J- (RI [in the formula ^, 11, l), X, Y and Z have the same meanings as above. 1 is an alkyl group or F, T
, indicates a nyl group. ] That is, pyrazole sulfonamide derivative (IV)
is reacted with chloroformate or carbonate in a solvent such as acetone or methyl ethyl ketone in the presence of a base such as potassium carbonate, and after the reaction is treated with an acidic substance such as acid to obtain compound (Vl). Next, the compound (+) of the present invention can be obtained by heating the compound (Ill) in a solvent such as toluene.

-Less than 1 margin Evening” 1 set 1 (IX) [In the formula, A, B and D have the same meanings as above.

E and FGJ halogen atom, R5 represents a lower alkyl group, and G represents a nitrogen atom or =CH- group. []] Referring to JP-A-56-154471, the compound (■) which is a part of the compounds of the present invention is prepared by reacting the pyrazole sulfonamide derivative (IV) with pyrimidine or triazine isocyanate (■). Compound (IX), which is also part of the compounds of the present invention, can also be synthesized by synthesis and then reaction with sodium alcoholade. Pyrazole sulfonyl isocyanate, the raw material used in Reaction Formula 1, is synthesized into pyrazole sulfonamide by the method described below, and further disclosed in JP-A-55-13'.
It can be synthesized by referring to the method described in Japanese Patent No. 266. Although the intermediate pyrazole sulfonamide is also a new compound, it can be synthesized by appropriately selecting several synthetic routes 1 to 1 described below.

One or less margin one (IV)
(n)i) POCl3 1i) Na5llezl (Be zl represents a benzyl group) iii) C12/ MeCOOH・
+120iv) N114011 v) l'23B vi) Na5H vii) Na0ll ・NlI4011 -NaOC
lviit) KMnO4 1X') 1,'N aN oZ + II C1
/2, SO2+copper salt x) n-Bu■OC [In the formula, A, 13, D, X, Y and Z have the same meanings as above. ] An example of the synthesis of the intermediate pyrazole sulfonamide used in the second invention is described below as a reference example.

Example 4-L 4-ethoxycarbonyl-! -Mejiru Pirazono 5-
Synthesis of sulbonamide =-,! Synthesis of ethyl 5-hydroxy-1-methylpyrazole-4-carboxylate 2168 diethyl nidoxymethylene malonate was dissolved in 216 g of ethane-ethanol, and methylhydrazine 4
68 was added at 10°C. Thereafter, the mixture was stirred at room temperature for 1 hour, and further heated under reflux for 1 hour. The precipitated crystals were filtered and dried to obtain the target compound +4h with a melting point of 134-135°C.

"knee? -Synthesis of ethyl 5-chloro-1-methylpyrazole-4-carboxylate A mixture of 10 g of ethyl 5-hy-10x-1-methylpyrazole-4-carboxylate and 50 ml of phosphorus oxychloride was mixed with 90 to 10 (1'C The mixture was stirred for 65 hours at . Excess phosphorus oxychloride was distilled off under reduced pressure, and the residue was poured into ice water.

When the precipitated crystals are filtered and dried, the melting point is 194-195℃.
4.5 g of 5-chloro-1-methylpyrazole-4-carboxylic acid was obtained. Further, the filtrate was made alkaline with aqueous ammonia, extracted with ether, dried, and then the solvent was distilled off to obtain 4.0 g of oily ethyl 5-chloro-1-methylpyrazole-4-carboxylate. 5 ~ Add 30 ml of thionyl chloride and 0.2 ml of dimethylbormamide to 4.5 g of chloro-1-methylpyrazole-4-carboxylic acid.
After heating under reflux for an hour, excess thionyl chloride was distilled off under reduced pressure and added to dry ethanol and alcohol. After stirring at room temperature for 3 hours, the solvent was distilled off, ether was added, washed with water, dried, and the solvent was distilled off.
4.5 g of ethyl -chloro-1-methylpyrazole-4-carboxylate was obtained. Total target object: 8.5g.

↓Nizu-5-mercapto-1-methylpyrazole-4-
Synthesis of ethyl carboxylate Add 2.2 g (0,094 mol) of sodium gold mud to 5 ml of ethanol; after melting, add 5 ml of dimethylformamide.
0ml was added and most of the ethanol was distilled off. Next, under cooling, hydrogen sulfide gas was blown in to saturate the 5-
7.4 g (0,039 mol) of ethyl chloro-1-methylpyrazole-4-carboxylate was added. 70~B
After stirring at θ°C for 3.5 hours, the mixture was concentrated under reduced pressure, ice water was added to the residue, and the resulting insoluble matter was filtered. After making the filtrate acidic, it was extracted with chloroform, and after drying, the solvent was distilled off.
6.8 g of oily target product was obtained.

Synthesis of 1-44-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide 5-mercapto-1-methylpyrazole-4-carboxylic acid: [chill 7, 20 ml of an aqueous solution of tg and 1.6 g of sodium hydroxide, 2 ))% was added to 100 ml of aqueous ammonia.

Add 61 g of 5% Na0C1 aqueous solution to 1 solution of this water bath.
Added at 0°C. The precipitated crystals were filtered and washed with water, and 5.6 g of the obtained sulfenamide was suspended in water, and a saturated aqueous solution of 5.5 g of potassium permanganate was added at room temperature.

After stirring vigorously at room temperature, the mixture was filtered and the filtrate was acidified and extracted with ethyl acetate. After drying, the solvent was distilled off to obtain 1.8 g of crystals of the desired product.

Synthesis of -14-dioxycarbonyl-1-methylpyrazole-5-sulfonamide (alternative method) 3.0 g of ethyl 5-mercapto-1-methinolipyrazole-4-carboxylate at a melting point of 102-104°C 15-20℃ in 50ml acetic acid solution
The mixture was stirred while blowing chlorine gas. Next, after blowing in nitrogen gas, the reaction mixture was poured into ice water and the precipitated crystals were separated by filtration.

The sulfonyl chloride obtained as described above was dissolved in 20 ml of tetrahydrofuran, and the solution was added to 50 ml of 28% ammonia water while cooling with water. After stirring at room temperature for 2 hours, the mixture was concentrated under reduced pressure, and the precipitated crystals were filtered, washed with water, and further washed with n-hexane. 1.3 g of dry warts was obtained. The melting point matched that of the previously synthesized product.

Synthesis of 4-Me1-:+-Dicarbonyl-1-methylpyrazole-5-sulfonamide Synthesis was carried out according to Reference Example 1 above.

Melting point 127-128℃ The physical properties of each intermediate are as follows.

Methyl 5-hydroxy-1-methylpyrazole-4-carboxylate Melting point 111-113°C Methyl 5-chloro-1-methylpyrazole-4-carboxylate Melting point 70-71°C 5-mercapto-1-methylpyrazole-4-carboxylate Methyl acid melting point 64-65℃

Synthesis of 4-chloro-1,3-dimethylpyrazole-5-sulponamide and 1,3-dimethylpyrazole-5-sulfonamide 3-11.Synthesis of 3-dimethyl-5-mercaptopyrazole 1.3- in 630 ml of xylene Add 84 g (0.75 mol) of dimethyl-5-hydroxypyrazole,
Heated to 10-120°C. Phosphorus pentasulfide 65.3g (0
, 294 mol) was added little by little, and the mixture was further heated under reflux for 1.5 hours. After filtration while hot, the solvent is distilled off to obtain crystals of the target product 21. h was precipitated. Melting point 130~132℃
Synthesis of 1-1,3-dimethylpyrazole-5-sulponamide Add 1,3-dimethyl-5 obtained above to 109 ml of acetic acid.
- 12 g (0,094 mol) of mercaptopyrazole and 15 ml of water were added. Chlorine gas was blown into this at 10°C until it became saturated. After stirring for 2 hours, the mixture was added to ice water, extracted with ether, and washed with water. After drying,
When the ether was distilled off, an oily 4-trifluoride 1:1 to 1
, 19.5 g of 3-dimethylpyrazole-5-sulbonyl chloride were obtained. Add this to 50ml of tetrahydrofuran
Dissolve it in a temperature below 10℃? It was dropped into 130 ml of 28% ammonia water at 1 degree. Room? After stirring in an FA Tr for 3 hours, a portion of the solvent was concentrated to precipitate crystals. This was filtered to obtain 10.8 g of target crystals. Melting point 135
~138°C 3-'Synthesis of 3-1.3-dimethylpyrazole-=5-fluoronamide'' The filtrate obtained when the target product sulponamide was filtered in Reference Example 3-2 was washed several times with Hensen. After washing, part of the water was distilled off under reduced pressure and concentrated, followed by extraction with ethyl acetate. The extract was dried and concentrated to obtain 4.0 g of the desired product. Melting point 63-66"C0- or below margin- pot-technical side 1. Synthesis of 3-dimethyl-4-nitropyrazole-5=sulbonamide A-21-5-chloro-1,3-dimethyl-4-21~
Synthesis of pyrazole Add 35g of concentrated sulfuric acid to 10ml of 90% concentrated nitric acid, and add 35g of concentrated sulfuric acid to 75~
5-chloro-1,3-dimethylpyrazole 1 at 85°C
3g ((1.1 mol) was added dropwise. After dropping, the temperature was 75-85°C.
The reaction mixture was poured into ice for 1.5 hours (stirred in a haze), and the precipitated solid was filtered once, washed with water, and dried to obtain 14.5 g of the target product. -Synthesis of 1,3-dimethyl-4-nitropyrazole To a solution of 21 g of 1-lium methoxide in 400 ml of dimethylformamide F, 50 ml of Hensyl mercaptan was added under water cooling.
．． 8 g (0,41 T-nyl) was added, followed by 65.2 g of 5-chloro-1゜3-syndi-4-nitropyrazole.
g (0.37 mol) was added. After stirring the reaction mixture at room temperature for 3 hours, dimethylformamide was distilled off under reduced pressure, and the residue was poured into ice water. When the precipitated solid was filtered, washed with water and n-hexano, and dried, 82.4 g of the target product was obtained as iii
It was done. Melting point 82-83℃ Soil, Main 1. 3~ Synthesis of dimethyl-4-dimethyl-1,3-dimethyl-4-pyrazole 408 (0,152 mol) in vinegar rM, 300n+I containing 30 ml of water The solution of tt'knee 3~ll''c: L,: -(1!,,1) was bubbled with elementary gas and stirred for 1.5 hours.Then, the reaction mixture was poured into ice water and diluted with ether. 1' by extracting
1,3-dimethyl-4-nito-1-pyrazole-5-sulfonylchloride 1'' manufactured by Ill. was obtained as a Ura method product.

The sulbonyl chloride obtained here was dissolved in 1 part of tetrahydrofuran, and this was dissolved in 1 part of 28% ammonia water.
50m+ under ice cooling. Stir at room temperature 1'1 51hj1
i) After step 1, concentrate under reduced pressure, filter the obtained solid, add water and
After washing with J-bitohexane and drying, the target object 1! 1
, fi (, H was subjected to IH. Melting point 138-140
'C1 friend 1 1.3-dimethyl-4-dimethylsulfamoylvirazole 5-sulfonamide synthesis-12,j N,N
Synthesis of -dimethyl-(5-chloro-1゜3-u'methylpyrazole)-4-sulfonamide 5-
30 g (0.23 mol) of chloro-1,3-dimethylpyrazole was added dropwise. After the dropwise addition, the mixture was heated and stirred at 100°C for 8 hours. After that, the temperature was lowered to 80°C and thionyl chloride 36
8 was added dropwise over 30 minutes. After the dropwise addition, the mixture was stirred at 100°C for 2 hours. Thereafter, the reaction mixture was cooled with ice water and carefully poured into ice water to obtain 50 g of t115-1:I-1,3-dimethylpyrazole-4-sulfonyl chloride as crystals.

Next, add 40 g of dimethylamine to 25 g of tetrahydrofuran.
The sulfonyl chloride was added to the solution under water cooling, and the mixture was stirred at room temperature for 3 hours. After the reaction, tetrahydrofuran was distilled off under reduced pressure, ether was added to the residue, washed with water, dried, and the solvent was distilled off to obtain 47 g of the desired product. Melting point 53-55℃-L2N,N-dimethyl-(5
-1, fucilnaor 1,3-dimethylpyrazole)-4
Synthesis of -Sulbonamide According to Reference Examples 4 to 2, N,N-dimethyl-(5-chloro-1,3-dimethylpyrazole)-4-no,irbonamide was obtained as a raw material.

Melting point: 108-109°C Synthesis of cephamoylpyrazole-5-sulfonamide N,N-dimethyl-(5-hensylthio-1, IM was performed using 3-dimethylpyrazole)-11-sulbonamide as a raw material.

Yutun 209-210℃ Synthesis of 4-(2,4-dichlorobenzoyl)-1-methylpyrazole-5-sulfonamide 1''52-5-chloro-4-(2,4-dichloro-・Synthesis of (2,1 dichlorobenzoyl)-1-methylpyrazole 4 (0,148 mol) of (2,1 dichlorobenzoyl)-5-hydroxy-1-methylpyrazole was added to 150 ml of phosphorus oxychloride and heated at 100°C for 6 hours. After the reaction, phosphorus oxychloride was distilled off under reduced pressure L2, added to ice water, and extracted with Hensen.The solvent was distilled off, and the target product 5 was extracted.
2. , ig was obtained as an oil.

-26-=2- 4-(2,4-dichlorobenzoyl)
Synthesis of -1-methyl-5-mercaptopyrazole 50 g of 1-1-4-(2,4-dichlorobenzoyl)-1-methylpyrazole, thorium bisulfide dihydrate (70%) 225B and ethanol 10100
The mixture of O was heated to reflux for 5 hours. After the reaction, ethanol was distilled off under reduced IF L7, and then water was distilled off at 500 ml.
Add n+ 1 to this]／・ノ! Pa, /Y extracted.

The aqueous layer was made acidic with concentrated hydrochloric acid and washed with 7ml of t7rl. The organic layer was washed with water and dried, and the solvent was distilled off to remove 41.4g of the desired product.

Melting point F) 1-・)(3°(' Isu-nihiro34-(2,4-dichlorobenzoyl)-1-
Synthesis of methylpyrazole-5-sulfonamide 1-4-<2,4-dichlorobenzoyl)-1-methyl-
5-Mercaptopyrazole 12.5. , acetic acid 120m
Add 3 to 8 chlorine gas to a mixture of 1 and 20 n + 1 water.
After the reaction was completed, the reaction solution was poured into ice water, and the precipitated solid was filtered, washed with water, and dried. This was added to 100 ml of 2%-1' ammonia water under water cooling. Stir at room temperature.
After 2 hours, the solid obtained by concentrating under reduced pressure was filtered, washed with water and n-hexano, and dried.
was iυ. Melting point: 165-167℃ Medicine dish 1 5-amino-1,3-dimethyl in a mixed solution of 118 ml of synthetic salt rv of 4-ethoxycarbonyl-1,3-dimethylpyrazole-5-sulfonamide, 18 ml of acetic acid, and 10 ml of phosphoric acid. 9.15 g (0.(15 mol)) of ethyl pyrazole-4-carboxylate was added. It was cooled to -10°C, and 3.8 g of sodium nitrite dissolved in 7.6 ml of water was added dropwise. Next, sulfur dioxide was added. 1.Og of cuprous chloride in 60W of acetic acid saturated solution
was added, and the previously prepared solution was added little by little into the solution that had been cooled to 0°C. At the end of the dropwise addition, the reaction solution was stirred for 1 hour at -Yf&H)'c, and the reaction solution was poured into ice water and extracted with ether to obtain 7.2 g of crude 4-ethoxycarbonyl-1,3-dimethylpyrazole-5-sulfonyl chloride. Obtained.

Here, the recovered sulfonyl chloride was dissolved in 1ml of tetrahydrofuran, and the solution was added to 40ml of 28% ammonia water under water cooling at a temperature below 10°C. After stirring at room temperature for 3 hours, the obtained solution was concentrated under reduced pressure. The resulting solid was filtered, washed with water, and dried to obtain 5.8 g of the desired product. Melting point 11 (i = 118°C 8") Synthesis Synthesized from methyl 5-amino-1,3-dimethylpyrazole-4-carboxylate according to Reference Example 7. Melting point 16
2-164℃ Vehicle weight 1. - 4-ethoxycarbonyl-1-phenylpyrazole-5
-Synthesis of sulbonamide From ethyl 5-amino-1-phenylpyrazole-4-carboxylate according to Reference Example 7 (synthesized 7).

Melting point 197-200°C 1 Control Uρ Synthesis of 4-ethoxycarbonylpyrazole-5(3)-sulfonamide 5 Synthesized from ethyl aminopyrazole-4-carboxylate according to Reference Example 7.

Melting point 179-180℃ Similar to car weight
Synthesis of 5-sulfonamide 13.8 g of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide was added to 100 ml of 50% methanol water containing 4.74 g of rythrium hydroxide.
The mixture was heated to reflux for a minute. After the reaction, the solvent was distilled off and the residue was
1 of water was added, and then 10% hydrochloric acid water was added.

When the precipitated crystals were filtered out, 4-lupoxy-
Crystals of 1-methylpyrazole-5-sulbonamide++
, ++C was pissed. Melting point: 192-195° C. Then, 13 g of the obtained sulfonamide 6.13 g was heated in 60 ml of n-butanol at 80° C. for 3 hours while blowing hydrogen chloride gas. After n-butanol was distilled off, the mixture was heated again at 80° C. for 3 hours with tobuknol and hydrogen chloride. After n-butanol was distilled off, the crude crystals obtained were subjected to p1 crystallization with benzene to obtain 5.8 g of the desired product.

A specific synthesis example of the compound of Ichiki's invention will be described below using the substituted pyrazole sulfonamides obtained in Reference Examples 1 to 11 with a melting point of 96 to 119°C, but the present invention is not limited thereto. There is no one.

Example 1 - N-((4,6-dimethoxypyrimidin-2-yl)
Synthesis of aminocarbonyl-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (compound N
o, 8) 5.0 g of 4-engineered 1-xycarbonyl-1-methylpyrazole-5 sulfonamide, 4.45 g of dry carlyrum carbonate
To a mixture of 50 ml of acetone was added 13 g of n-butyl isocyanate at room temperature, and the mixture was stirred under continuous heating for 3+ hours. After the reaction, acetone was distilled off under reduced pressure and
Ice water was added to the residue, and insoluble matter was filtered. Precipitate the strained liquid with hydrochloric acid and obtain 111゛ crystals. Separately, wash with water, dry
-(Dobutylcarbamoyl)-4-ethoxycartonyl-1-methylpyrazoyl-5-sulponyl/amide5.
1g of the mixture was added to a drying tank (17120ml), heated under reflux, 9.1g of phosgene was blown in, and then added for another 1.5 hours.
44 tl flowed. After the reaction was completed, it was concentrated under reduced pressure to remove the crude sulfonyl isocyanate. This crude sulfonyl isoyu′/
0.4111 g of annate was added to 2-amino-4,6-synthoxypyrimidine 40 (1 mB of dry ace[nitrile 2
(l m l 熔?Il.

and stirred at room temperature. The generated crystals are separated by 1.5,
By washing and drying the object 0.88 i!
I...

Melting point 170-172°C Example N-((4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1
-Synthesis of methylpyrazole-5-Z-1-amide (
Compound No. 2) Using the sulfonamide obtained in Reference Example 2, N-<n-butylcarbamoyl)-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide is obtained according to the method of Example 1. Melting point 88-90
℃. Furthermore, according to Example 1, sulfonylisocyanate-1
The desired product was obtained by reacting . with 17.2 amino-4-methoxy-6-methylpyrimidine. Melting point 1
83-184°C.

Example N-Synthesis of [(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-chloro-1,3-dimethylpyrazole-5-sulfonamide (compound No.)
5) (1) N-(ethoxysulfonyl)-4-chloro-1,
Synthesis of 3-dimethylpyrazole-5-sulfonamide In 30+nl of dry acetone, 2.1 g of sulfonamyl obtained in Reference Example 3-2, 1.73 g of potassium carbonate,
Ethyl chloroformate 1.41. was added and stirred at room temperature for 18 hours. The solvent was distilled off, water was added, acidified with concentrated hydrochloric acid, and extracted with 1(:[--chill). After drying and concentrating the organic layer, the precipitated crude crystals were recrystallized with a mixed solvent of benzene-hexane. 2.0 g of the target product was obtained.

Melting point: 106-109°C (2) Synthesis of N-((4,6-dimethylpyrimicin-2-yl)aminocarbonyl]-4-chloro 1°3-dimethylpyrazole-5-sulbonamide Add the above compound 1 to 10ml of xylene. .41 g, 0.74 g of 2-amino-4,6-dimethylpyrimidine was added, and 2
The mixture was heated to reflux for an hour. When the mixture was left to stand at room temperature, 1.2 g of the target product precipitated. Melting point: 191-194°C.

Jitsuebenj - Raw N-((4,6-simethoxypyrimicin-2-yl)aminocarbonyl)-4-ethyl-1-quincarbonylpyrazole-5 (3)-Synthesis of sulponami 1 (Compound No. ,
64) (1) Synthesis of r, I-phenoxycarbonyl-4-ethoxycarbonylpyrazole-5(3)-sulbonamide 4-1 Toxicityluponylpyrazole-5(3)-sulponamyl” 8.76 fl dimethyl Formamide 40
1I11 solution 55 Sodium silohydride 1.75g dimethylborumamide 15ml 1ft! It was added dropwise to the cloudy solution while cooling with water. Next, a solution of 8.56 g of diphenyl carbonate in 30 ml of dimethylformamide was added dropwise under water cooling, and the mixture was stirred overnight at room temperature. The precipitated solid was collected by filtration and mixed with 50ml of 5% hydrochloric acid, 5ml of ice and 300ml of ethyl acetate.
1 of the mixture and stirred. After washing the organic layer with water, dry it.
After concentration, the precipitated 111 crystals were washed with ether and dried, and the desired product was obtained! +, (l 1. was obtained.

Melting point: 153-155°C (2) Synthesis of N-((4,6-cymethoxypyrimidin-2-yl)aminocarbonyl]-4-oxycarbonylpyrano'-5(3)-sulfonamide Into 10 ml of anhydrous dioxane, the N-phenoxycarbonyl-4-ethoxycarbonylpyrazole obtained above was added.
1.02 g of 5(3)-sulfonamide and 465 rra of 2-amino-4,6-dimethoxypyrimidine were added, and the mixture was heated under reflux for 1 hour. After the reaction was completed, dioxane was distilled off under reduced pressure, and 5n11 of benzene was added to the residue and stirred. The precipitated crystals were filtered through a sieve, washed with ethyl chloride, and dried to obtain 0.92 g of the desired product. Melting point 1
89-191 "C Next, the physical property values of the compounds synthesized according to the above examples are shown in Table 1 below, along with the compounds synthesized in Examples 1 to 4. The compounds of the present invention have 1; p It is not determined.

-Space below- ne: methyl: 'pj F,? : Ethyl 1 2.4
-CI, Bnz: 2,4-dichloro)b<7 zoyl group Pll: p54nyl group Bu-n: n-butyl group
represents.

- Space below 1 The compound of the present invention is generally applied as a herbicide using a suitable carrier, such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, or water, alcohol (methanol, ethanol, etc.) , aromatic W group hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ether la'n, u-L: / J, 4't, esters (ethyl acetate, etc.), acid amides ( It can be applied by mixing it with a liquid carrier such as dimethylbormamide (dimethylbormamide, etc.), and if desired, emulsifiers, thickening agents, clouding agents, penetrants, spreading agents, stabilizers, etc. can be added. It can be put to practical use in any desired dosage form, such as emulsion, wettable powder, powder, or granule.

Examples of formulations of herbicides containing the compound of the present invention as an active ingredient are shown below, but the invention is not limited to these.

In addition, in the following formulation example, ``Part j has a flavor of 81%.

1. Hydrating agent Compound of the present invention No. 3 -----・-----,
, 50 parts Siegrite Δ −−1−−−・−1−4
Part 6 (Kaolin clay: Sieglite T industrial goods) Product name) Tsurupol 5 (13!) ・--- Part 2 (Non-
Io: Mixture of dielectric surfactant and anionic surfactant 2 Toho Chemical (Kiku brand name) Carplex (anti-caking agent) - 2 parts (10 wide carbon: Shionogi & Co. brand name) The above mixture is uniformly mixed and pulverized to form a wettable powder. When using, add 50% of the above hydrating agent.
It is diluted ~50,000 times and applied so that the amount of active ingredient is 0.005 kg to 10 kg per hectare.

n [Color luLs Wettable powder Compound of the present invention No. 8---1・-----7
Part 5 Sea Cry 1Δ −−−−−−−−−−−−−～
19 parts (Kaolin thread 1.-' - Niji-Krite Kogyo (■Product name) Tsurupol 5039 -------=-2
part (mixture of nonionic surfactant and anionic surfactant: Toho Kagaku Pilgrimage) trade name) Curve 2. Kus (anti-caking agent) --- 4 parts (Bois carbon: Shionogi) Pharmaceutical products (product name) are uniformly mixed and pulverized to make wettable powders.

Formulation - Example - 1 - Hydrating agent Compound of the present invention No. 12. ,−,−,,−−−−,
5 Q section seek cry i・△ −−−−−−−−−1
+ 7 parts (Kaolin light Ray: Sieglite T-gyo Q11 commercial crystal 1),) Tsurupol 5039 --- 2 parts (non-ionic surfactant and Annie', /Sex'7F +
Mixture with fii activator: Toho Chemical (4M3 trade name) Carplex (anti-caking agent) 2 parts (white carbon: Shiono 4-ren f (ll product/, p, )) Mix and grind evenly on a ginoru and sprinkle with water. Japanese medicine and talent.

Loss of 19L of R Hydrating agent Compound of the present invention Nosu ----, -25 parts Ziclaite △ -1---71 parts (Kao I/Kiri Reniji! Cry l-T↑7) Product 1'
1) Tsurupol 5 (139--------2 parts (mixture of nonionic surfactant and anionic!Si'Ii/II activator: Toho Chemical (trade name) Curve L/ NOX (Anti-caking agent) 2 parts (White Carbon: Shionogi & Co., Ltd.) Product/?1) Mix and grind the above ingredients evenly and use it as a wettable powder.

Hydrating agent Compound of the present invention Positive 5N-----50 parts Siclaite△--1------・--------
・-44 parts (kaolin light/'/1) -1 Sieglite Industries product name) Tsurupol 5039 -1----------------------
------4 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Ogiku brand name) Carplex (anti-caking agent) ---2 parts (Boyte carbon: Shionogi & Co. ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder.

Formulation example - Hydrating agent Compound of the present invention Teeth, i ---------・------
Part 45 Seecry 1-A-・----11------
・-51 parts (Kaolin-based I7re: Sieglite Kogyo ■
Product name) Tsurupol 5 fl 39 -=-1---
−−−−−−−−2 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical brand name) − Carplex (anticaking agent) −−−2 parts (white Carbon: Shionogi & Co. ■Product name) The above is mixed and pulverized uniformly to make a wettable powder.

■ Combined 1-7 emulsion Compound of the present invention 1----- 2 parts xy
- 78 parts dimethylformamide - 15 parts Tsurpol 2680 - 5 parts (mixture of nonionic surfactant and anionic surfactant) : Toho Kagaku brand name) Mix the above ingredients uniformly to make an emulsion. When used, the above emulsion is IO to 10. Diluted to O'00 times L5 and active ingredient M
kkahe') Tar hit? Q O, 005 kg ~ l O
Spread it to make a total of kg.

JI! , gold side” - Flowable compound of the present invention! llo, 5g ----- 25 parts Agelisil S-710-in part (nonionic surfactant: Kao Atlas (11) trade name) Lunosox I 000 G ---ni (1.5 parts (anionic surfactant: Kao Atlas (11) product name) Activator: Toho Kagaku A1 trade name) 1% rhodobol water ------------------------ 20 parts (thickener:
Lone Boulin product name) Water
--1-----------44, 5 parts or more of J: are uniformly mixed to prepare a flowable agent.

Formulation Example 9 Granules Compound of the Invention No. 52--1 0.1 parts Hentoni I-1--55.0
part talc =−−−−1−−−−−1・−
After uniformly mixing and pulverizing 44.9 parts or more, a small amount of water is added, the mixture is stirred and kneaded, the granules are increased using an extrusion type granulator, and the mixture is dried to form granules.

Granules Compound of the present invention No. 3-・-----1----0
, 5 parts Bentonai I-----------------------55,
0 parts talc −−−−−−−−−−−4
After uniformly mixing and pulverizing 4 to 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.

Poor mouth resistance 11% Granules Compound of the present invention NOTE 5---------- 1.0 parts Pentosu・It --------------1・-
55.0 parts talc −−−−−−−−−−
After uniformly mixing and pulverizing 44.0 parts or more, a small amount of water is added to the mixture until Ifit1≧mixing, the granules are enlarged using an extrusion type granulator, and dried to form granules.

In addition, the compound of the present invention may be used in preparations or lt! l
It may be applied in combination with other types of herbicides, various insecticides, step-filtering agents, etc. at the time of cloth application.

Other types of herbicides mentioned above include, for example, fu, y-j, ・
GEMICALS, HANDBOOK (Farm Chemica)
lslandbook) 68th edition (1982).

In addition, the compound of the present invention can be used in fields other than agricultural and horticultural fields such as fields, paddy fields, and orchards, as well as playgrounds, vacant lots, railway edges, etc.
It can also be applied to control various weeds in cultivated land.
The amount of the applied drug varies depending on the situation, application time, application method, target grass species, cultivated crops, etc., but in general, the appropriate amount of active ingredient is 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.

Extraction example knee ↓ Weeding effect test by soil treatment N & s
Put sterilized diluvial soil in a plastic box measuring 5 cm, width 22 cm, and depth 5 cm, and grow rice, wild grass, crabgrass, cyperus, koakaza, purslane, leafminer, etc.
Dog mustard was mixed and covered with soil to a depth of about 1.5 cm, and then the active ingredient was evenly distributed over the soil surface in 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.

The results are shown in Table 2.

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

Judgment 11Lj4 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 to 20% () - Weed killing rate 5% or less (hardly effective) (old -
The weed killing rate shown in -Lx was determined by measuring the weight of grass in one part of the land in the chemical treatment area and the above-ground grass weight in the untreated area, and using the formula shown in -1.

Plasti of length 15cm, width 22cm, depth 5 can,
Put the sterilized diluvial soil in a box and add rice, crabgrass, cyperus, koakaza, leafminer, dogmustard, 1.
- Seeds of sorghum, soybean, wheat, and sorghum were sown in spots and covered with soil to a depth of about 1.5 cm. When the various plants reached the 2-3 leaf stage, the grass was uniformly sprayed so that the amount of self-supporting material was at a predetermined ratio.

At the time of spraying, the chemical solution was prepared by diluting the hydrating powder of the formulation example above with water and spraying it over the entire surface of the stems and leaves of various weeds.

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 3.

Test example-3 Herbicidal effect test under flooded conditions 1150
After putting alluvial soil in Wagner Bosoto of 00 ares,
Add water and mix to create freshwater conditions at a depth of 2 cm. Seeds of R. japonicus, P. japonicum, Japanese azalea, Kikasig. j', and Firefly.

Furthermore, rice seedlings at the 2.5 leaf stage were transferred. The next day, a diluted solution of the second drug was dropped onto the water surface using a measuring pipette to a predetermined dose.

Three weeks after the chemical solution treatment, the herbicidal effect on various weeds was investigated according to the 1' standard 1F of Test Example 1. The results are shown in Table 4.

Control compound Δ (described in JP-A-56-169688)
Control compound B (! I5 Kaisho 56169688℃ public (・1
) vs. 11 (1 Compound C (Japanese Unexamined Patent Publication No. 56-169
No. 688 Publication: 1.
(:) Continuation of Table 2, Table 3, Table 4, Page 1 39100 311100 722-1 Nissan Chemical Industries, Ltd. Central Research Laboratory Author: Takashi Inokai 0: Shiraoka, Shiraoka-machi, Minamisaitama-gun, Saitama Author: Toshihiko Oguchi 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Prefecture Inside the Biological Chemistry Research Institute, Nissan Chemical Industries, Ltd. Continuation of amendment (spontaneous) October 91, 1980 Kazuo Wakasugi, Commissioner of the Japan Patent Office ■ Indication of the case 1982 Patent Application No. 70407 2 Name of the invention Pyrazole sulfonylurea derivative, its 'IIJ? b
and Selective Herbicide 3 Containing the Derivatives Relationship with the Amendment Case Patent Applicant Address 101 3-7 Kanda Nishiki-cho, Chiyoda-ku, Tokyo Name (39B) Representative of Nissan Chemical Industries, Ltd.
Misao Kusano (contact phone number (1474-65-fill) 4
Voluntary amendment with an amendment order 5 Detailed description of the invention in the specification subject to amendment 6 Contents of the amendment ``Unexamined Japanese Patent Publication No. 169988'' on page 6, line 1 of the specification issue d1 pressure.

Procedural Amendment I Indication of the Case 1982 Patent Application No. 70407 2 Name of the Invention Pyrazole Sulfonylurea 6B > 7, Process for Producing the Same,
and Selective Herbicide 3 Containing the Derivatives Relationship with the Sleeve Straightening Case Patent Applicant Address 3-7-1 Kanda Nishiki-cho, Chiyoda-ku, Tokyo Name (
39B) Nissan Chemical Industries, Ltd. 5 Number of inventions increased due to sleeve correction 16 Claims column of specification q subject to amendment and Detailed description of invention column 7 Contents of amendment (11 Scope of claims after amendment amended as shown in the attached sheet.

(2) On page 17, line 18 of the specification, the phrase ``precipitated crystals were filtered out'' was replaced with [Hensen extraction, drying, and evaporation of the solvent to form an oily 4-dioxycarbonyl-1-methylpyrazole- 5-sulfonyl chloride (boiling point 130/1.2
+++ml1g) was obtained. ” he corrected.

(3) Insert the following additionally between the 9th and 10th lines of the 29th line of the details.

Synthesis of Reference Example 1-1-Hairienkon 4-'' 21-dicarbonyl-5-sulponamide F 1.36 g of diethyl sulfate was added to 3.5 g of the sulponamide obtained in Reference Example 1O, and the mixture was heated to 1.5 g at 150°C. The mixture was heated and stirred for hours. After cooling the reaction mixture, add 30 ml of ethyl acetate.
Then, 30 ml of ice water and 10 ml of a saturated aqueous solution of hydrogen carbonate and hydrochloric acid were added. Dry the ethyl acetate layer and remove the solvent.
.

Distillation to give 4-ethoxycarbonyl-1-ethylpyrazole-5-sulfonamide and 4-ethoxycarbonyl-
1-Ethylpyrazole-3-sulfonamide mixture 2
．． 8g was obtained. The desired product was obtained from the mixture using silica gel chromatography (eluent: ethyl acetate/methanol = 5/l). h was isolated. Melting point: 147-152℃ 4-Ethoxycarbonyl-1-t-butylpyrazole-
Synthesis of 5-sulfonamide 13-1 Synthesis of ethyl 1-L-butylpyrazole-4-carboxylate In a mixed solution of 15.5 g of concentrated sulfuric acid, 60 ml of phosphoric acid (85%), and 200 ml of water, 3-amino- 31.7 g of ethyl 1-t-butylpyrazole-4-carboxylate was melted and cooled to 0 to 5° C., and 11.4 g of sodium nitrite dissolved in 40 ml of water was added dropwise. The diazotization reaction solution was added dropwise to 50 g of hypophosphorous acid aqueous solution at room temperature.

After stirring at room temperature for 1.5 hours, 28% aqueous ammonia was added until the pH reached 116, followed by extraction with ether, washing with water, drying, and evaporation of the solvent to obtain 29.1 g of the target compound in the form of an oil.

13-2 Synthesis of 4-ethoxycarbonyl-1-t-butylpyrazole-5-sulbonamide 9.8 g of ethyl 1-t-butylpyrazole-4-carboxylate was suspended in 100 ml of dry ether and cooled to below -60°C. did. Then, an ether solution of lithium diisopropylamide (1.2 times the mole) was added dropwise. The mixture was stirred as it was for 1 hour, and then sulfur dioxide gas was blown into the mixture for about 30 minutes. After reacting at -60°C for 1 hour, the mixture was further stirred at room temperature for 2 hours. The precipitated crystals were filtered and dried to obtain 12 g of solid 4-ethoxycarbonyl-1-butylpyrazole-5-sulfonic acid lithium salt.

Next, mix this with 200ml of ice water and 150ml of dichloromethane.
ml of solution, add 6.4 mL of N-chlorosuccinimide
g was added at a temperature of 0-5°C. After stirring at room temperature for 45 minutes, the dichloromethane layer was separated, and the aqueous layer was added with dichloromethane 1
00ml was extracted and totaled. The obtained dichloromethane solution of 4-ethoxycarbonyl-1-t-butylpyrazole-5-sulfonyl chloride was added dropwise to 159 ml of aqueous ammonia (28.chi.) cooled to 10.degree. C. or lower. After stirring at room temperature for 1 hour, the solvent was distilled off to obtain 5.1 g of the desired sulbonamide.

Melting point 109~ll’c Hair pulling bandan 4-Ethonidodicarbonyl- Sol- It was synthesized according to the method of Reference Example 13.

Melting point: 130-135°C" (4) "Crude sulfonyluy" on page 30, line IO of the specification box was corrected to "crude 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonyluy", same line 11. After “Socyanato”, “(boiling point 110℃ 10.07mm
Hg) Insert additional J.

(5) The following is additionally inserted between lines 5 and 6 of section 34 of the specification.

[Fruit spot] Synthesis of N-((4,5-dimethoxypyrimidin-2-yl)aminocarbonyl-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (compound 11)
h8) (IIN-(ethoxycarbonyl)-4-ethoxycarbonyl-l-methylpyrazole-5-sulfonamide 4-ethoxycarbonyl- in 30 ml of dry acetone)
1-Methylpyrazole-5-sulfonamide 4, 66g
, ethyl chloroformate 2.5 g, anhydrous potassium carbonate 4.
14 g was added and refluxed for 3 hours. After cooling, acetin was distilled off, ice water was added, insoluble materials were removed, and then acid precipitation was performed with hydrochloric acid. After extraction with ether, drying, and distillation of the solvent, crystals were precipitated from a mixed solvent of benzene and xane. Obtained m 5, 4 g Melting point 110-112°C (21 + 1- ( (4. 6-
(cymethoxypyrimidin-2-yl)aminocarbonyl)
-4-ethoxycarbonyl-1-methylpyrazole-5
- Sulfonamide 2.5 g of the sulfonyl carbamate obtained in 1 ml of toluene and 1.4 g of 2-amino-4,6-simethoxypyrimidine were added to 20 ml of toluene, and the mixture was refluxed while gradually distilling off the toluene. The reduced amount of toluene was added from time to time. After 8 hours of reflux, some of the toluene was distilled off, and when the mixture was left to stand, crystals of the target substance precipitated.

Obtained m 3.1g Melting point 170-172°C
yl)aminocarbonyl-4-ethoxycarbonyl-
Synthesis of 1-methylpyrazo-5-sulbonamide (Compound 9) (IIN-(soenoxycarbonyl)-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide 55χ thorium hydride in 10 ml of dimethylbormamide) 0.436 g and 2.33 g of 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide were added. Next, 2.57 g of diphenyl carbonate I was added under water cooling.
was added and stirred overnight at room temperature. Next, after distilling off dimethylbormamide, the residue was washed with ether and dissolved in ice water. After removing insoluble matter, the mixture was acidified with hydrochloric acid to precipitate a solid. After extraction with Hensen, the extract was dried, the solvent was distilled off, and crystals were precipitated from a mixed solvent of benzene and hexane.

Bone mass 3. Og Melting point 103-106℃ (21N-((
4-Methoxy-6-methyltriazin-2-yl)aminocarbonyl 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide 1- In 10 ml of anhydrous dioxane, the sulfonyl carbonyl H obtained in step 11, 8 g and 0.71 g of 2-amino-4-methoxy-6-methyltriazine were added and heated under reflux for 1 hour. After the reaction was completed, the solvent was distilled off and a small amount of Hensen was added to the residue. When left to stand, crystals precipitated. Obtained 110.8 g.
Melting point 138-139°C Example 7 N-((4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl-4-ethoxycarbonyl-1
- Synthesis of methylpyrazole-5-sulbonamide (compound N07) According to Example 5, N-(methoxycarbonyl)-4-ethoxycarbonyl-1-methylpyrazole-5-sulbonamide was synthesized using methyl chloroformate. Melting point: 93-95° C. Then, the desired product was obtained by reacting with 2-amino-4-methoxyl 6-methylpyrimidine in the same manner as in Example 5.

Melting point: 152-154° C.” (6) On page 34, line 7 of the specification, “1 Examples 1-4” is corrected to “Examples 1-7.”

(7) Add the following to the end of Table 1 on page 39 of the detailed accounting.

[“I “I °1” Attachment 2, Claims (1) General formula (■): [In the formula, a hydrogen atom, a lower alkyl group, or a phenyl group is shown. 0 represents a hydrogen atom or a lower alkyl group. D
is a hydrogen atom, C00II (R represents a lower alkyl group), C0Ar (Ar represents a phenyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, or 5O2NR'R''(R' R2 each represents a lower alkyl group.
Z may be a nitrogen atom or -C-R' (R3 may be a hydrogen atom or together with Y form a 5-membered ring structure containing an oxygen atom.

) is shown. ] A pyrazole sulfonylurea derivative represented by

(2) General formula (It): 8 [Formula LIJ/l represents a hydrogen atom, a lower alkyl group or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D represents a hydrogen atom, C00Ii (+1 is lower)' alkyl group. ), CO^r (Ar represents a phenyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, or 5(lzNR'l?"(R'
R'' each represents a lower alkyl group.] A birazolesulfonylisocyanato derivative represented by the following formula (■): ゝV [wherein X and Y are each independently Z represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group, and Z is a nitrogen atom or
73 (113 may form a 5-membered ring structure containing 6.1 oxygen atoms together with a hydrogen atom or V). ] General formula (I) characterized by reacting an aminopyrimidine or an aminotriazine derivative represented by the following in an inert solvent: ε In the formula, A represents a hydrogen atom, a lower alkyl group, or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D
is a hydrogen atom, GOOR (R does not represent a lower alkyl group)
, C0Ar (Ar represents a phenyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, or 5O2NR'll''(R'l?2 each represents a lower alkyl group), , x and Y each independently represent a hydrogen atom, a lower alkyl group, a lower alkyl group, a halogen atom, or a dimethylamino group; 1.2 is a nitrogen atom or -C-R' ([+3 is a hydrogen atom or V A method for producing a pyrazole sulfonyl urea-inducing compound represented by:

TAHASO□NL! 'l+2 (R'R2 is each lower class 1) kM to Uiaf jJ et al-L B, 1] O-1,.

8.N72""'5O2NIIGOOR'
(V) Indicates the entry by the following formula - ('' nee 辷 2 imitation 斌 - RUYOU 14. D is a hydrogen atom, COO (rj-'' A is 4° above.), CO^r (^ r is) λ (4) general formula (
I): [In the formula, ^ represents a hydrogen atom, a lower alkyl group, or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D is a hydrogen atom, C0OR (R represents a lower alkyl group), C0Ar (Ar represents phenyl 2B which may be substituted with a halogen atom), a halogen atom, a nitro group, or 5OJll'R2 (R' R2 each represents a lower alkyl group. X and V each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group, and Z
is a nitrogen atom or =C-R"(1 (3 may be a hydrogen atom or together with Y form a 5q ring structure containing an oxygen source Y.

) is shown. ] or 24 (k to t) as an active ingredient.

Claims (3)

[Claims] (1) General formula (I): [In the formula, represents a hydrogen atom, a lower alkyl group, or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D
is a hydrogen atom, C0OR (R represents a lower alkyl group)
, C0Ar (Ar represents a phenyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, or So, NR' I? "(R'R" each represents a lower alkyl group). X and Y each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group,
2 is a nitrogen atom or =C-R” (R is a hydrogen atom or V
A five-membered ring structure containing an oxygen atom may be formed together with the above. )
shows. ] A pyrazole sulfonylurea derivative represented by (2) General formula (■): 8 [In the formula, ^ represents a hydrogen atom, a lower alkyl group, or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D
is a hydrogen atom, C00I? (R represents a lower alkyl group), COAr (Ay- does not represent a phenyl group which may be substituted with a halogen atom), a halogen atom,
Nitro group, or 5O2NR' l? ” (R' R”
each represents a lower alkyl group. ) is shown. ] A pyrazole sulfonyl isocyanate derivative represented by the following formula (III): represents a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group, and 2 is a nitrogen atom or -
C-R" (R3 may form a 5-membered ring structure containing an oxygen atom together with a hydrogen atom or y).] An aminopyrimidine or an aminotriazine derivative represented by General formula (1) characterized by the reaction: [In the formula, A represents a hydrogen atom, a lower alkyl group, or) 1. Enyl group. B represents a hydrogen atom or a lower alkyl group. D represents a hydrogen atom. , C0OR (R represents a lower alkyl group), C0Ar (Ar represents a phenyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, or SO□NR11+" (Ill and R2 are each (lower alkyl group). X and Y each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group, and Z represents a nitrogen atom or =C-R' (R represents a hydrogen atom or an oxygen atom together with Y) may form a five-membered ring structure containing ] A method for producing a pyrazole sulfonylurea derivative. (3) General formula (■): [In the formula, represents a hydrogen atom, a lower alkyl group, or a phenyl group. B represents a hydrogen atom or a lower alkyl group. D
is a hydrogen atom, Cool? (R represents a lower alkyl group), CO^r (^r represents a phenyl group which may be substituted with a)\rogen atom. ), a halogen atom, a nitro group, or So, NR'R'' (R1 and R'' each represent a lower alkyl group). X and Y each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dimethylamino group,
Z represents a nitrogen atom or =C-R15 (R3 may form a hydrogen atom or a 5-membered ring structure containing an oxygen atom together with Y). ]. ] A selective herbicide characterized by containing one or more pyrazolesulfonylurea derivatives represented by the following as an active ingredient.