JPS6078981A - Pyrazolesulfonylurea derivative, its preparation, and plant growth regulator and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (A is H, lower alkyl, etc.; B and D are H, lower alkyl, halogen, nitro, etc.; E is H, or lower alkyl; Q is O, or S; X is H, CHClF, CHBrF, etc.; Y is H, lower alkyl, halogen, CF3, etc.; Z is N, or CH). EXAMPLE:N-[ ( 4-Difluoromethoxy-6-methylpyrimidin-2-yl )aminocarbonyl ]-1,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide. USE:A selective herbicide, and a plant growth regulator. Showing high safety to important crops, exhibiting high herbicidal activity with a small amount of it, useful as a herbicide for orchards, and nonagricultural lands. PREPARATION:A pyrazolesulfonyl isocyanate derivative shown by the formula IIis reacted with an aminopyrimidine or aminotriazine shown by the formula IIIto give a compound shown by the formula I .

Description

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

JP-A-58-148879 and EPC (application number 83101870.0) disclose pyrazole sulfonylurea derivatives; 77870
No. 58-126873 and JP-A-58-126873 contain substituted difluoromethoxy groups or ha? If f? '; It is described that sulfonylurea derivatives containing pyrimidine and triazine having a fluoromethylthio group are useful as herbicides.

It is essential to use herbicides to protect the city's key crops such as rice, wheat, corn, vines, and ivy from weed damage and increase yields. Particularly in recent years, in areas where these useful crops and weeds coexist, the same u1 treatment is applied to the stems and leaves of crops and weeds. A highly selective herbicide is desired.In addition, it is desirable to have an economical cost I
・From the perspective of reduction, etc., search research has continued for many years to find compounds that can achieve a high herbicidal effect at the lowest possible dose.
There is C.

Some of the compounds with similar properties are currently used as selective herbicides, but some of the newer compounds with these properties are currently used as selective herbicides. , Kaname also exists.

In order to develop selective herbicides for important crops, the present inventors have used a number of methods to develop selective herbicides for important crops. The herbicidal properties of compounds have been investigated. As a result, the compound of the present invention represented by the general formula (1) (111) has high herbicidal activity against many weeds in both the ±1-year treatment and the foliage treatment, and the compound of the present invention represented by the general formula (1) has high herbicidal activity against many weeds, and The present invention has been achieved by discovering that -C has higher safety against important crops compared to derivatives and substituted ginsylolome I-kin groups or substituted difluoromethylnao groups and sulbonyl urea 3A containing bilyzines and triazines. completed. 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-tno1 areas.

Furthermore, when used at low concentrations, the compound of the general formula (1) also has a strong plant growth regulating effect, which results in an increase in cultivated crops or yields. Shortening and strengthening of the stems by use of inhibiting crop height growth also results in a reduction or elimination of the risk of pre-harvest lodging, which in turn leads to pre-harvest increase.

The compound of the present invention represented by the general formula (1) is a new compound, and can be easily produced according to Reaction Formula 1 or 2 below.

[Hydrogen atom, lower)' represents a phenyl group optionally substituted with an alkyl group, a lower alkyl group, a halogen atom, or a 21-group.

B and B each independently represent a hydrogen atom, a lower alkyl group, a halogen atom, a 2I'UJ group, a lower 7-alkoxy group,
Haloalnitrile (-7lylalkyl, allyl, propargyl, lower J' alkoxyalkyl, haloalkyl, lower alkoxycarbonylalkyl, or hensyl group is not shown), CONJ
lh (J is a hydrogen atom, a lower alkyl group or a phenyl group, R2 is a hydrogen atom or a lower alkyl group, or Ri R2 are together - ((:II 2
) m - (m indicates an integer of 4.5 or 6.)
-C112C112 0 C112 C112- or -CH2 Cth N- (CI+3)C112 C
112-1 is shown. ), SOn113 (n represents an integer of 0.1 or 2, R3 represents a lower alkyl group, phenyl group or allyl alkyl group) S(12 NR4
R5 (R4 is a hydrogen atom or a lower alkyl group
represents a lower alkyl group, or R4 +rs taken together - (Cl12)m- (m represents an integer of 4.5 or 6) C112CI+2 0 C112 C11
2- or -C 11 2 C 11 2 N - (
C II 3) C112 CI+2-. ) or a phenyl group which may be substituted with a lower alkyl group, a halogen atom, or a nitro group. E represents a hydrogen atom or a lower alkyl group. 0 represents an oxygen atom or a sulfur atom, and X represents a hydrogen atom , CIICIF group, Cl
Indicates lBrF group, CIIP2 group or CIIFCF3 group. Y is a hydrogen atom, a lower alkyl group, a halogen atom, C
F3J%, -furkyl-J'mino group, dialkylamino group, lower "rruJ1giso-11, or 0CIIFz group. Z represents a nitrogen atom or a C11 group.] Naturally, pyrazole sulfonyl iso So7nar1 derivative is dissolved in a sufficiently dried inert solvent such as cyogysan, acet-'-I-lyl, etc., and 1r-minopyrimidine or '1''-minopyrimidine represented by formula (II) is added to the solution. By adding the derivative and stirring for 1'min, the reaction generally occurs quickly to yield the compound (1) of the present invention. If the reaction is difficult to proceed, the reaction may proceed easily by adding a small amount of a suitable base such as triethylamine, 1-lyethylenediamine, pyridine, sodium alumina, sodium hydrogen, etc. do.

The 1ift oni:11 pizolesulfonyl isocyanate used in the above reaction formula is 4.11 Kaisho 5εI
-148879, patent application No. 1420 G9 1987
Publication No. 57-228261 Shikobe Hu-1
1, S condylar number 5870407, patent application No. 1973
22.
It can be synthesized by referring to the method described in JP-1546112.

The aminopyrimidine or aminotriazine derivative used in the above reaction scheme can be synthesized by referring to the methods described in JP-A-58-23676 and JP-A-58-38264.

Reaction formula 2 (1) [Into the formula, B, D, E, [7, X, Y, I: N, koZ
It has the same meaning as 4Jliif. 1 to 6 represent an alkyl group or a phenyl group. That is, the pyrazole sulfonamide derivative IV) is reacted with ester of LJ sulfuric acid or a carbonic acid ester in a solvent such as acetone or methyl enalgel in the presence of a base such as potassium carbonate. After the reaction, compound (1) is prepared by treating with an acidic substance such as hydrochloric acid.

Then, in a solvent such as toluene, compound (Ill) and h
The compound (1) of the present invention can be purified by H4r.

Specific examples of the compounds of the present invention are shown in Tables 1 to 3, but they are not limited to the compounds of the present invention.

Compound teeth are referred to below.

-Margin below- Table 1 Table 2 A CY Table 3 Ne: Methyl group El Ethyl group Pl.; Propyl group B
u Nibutyl group Ph: Indicates a phenyl group.

Specific synthesis examples of the compounds of the present invention will be explained below in the margins, but the present invention is not limited thereto.

Fugomasu J N-((4-difluoromethoxy-(i methylpyrimidin-2-yl)aminocarbonyl)-1,,3-dimethyl-5-methoxycarbonylpyrazole-4-sulfonamide synthesis (compound tooth 20 )1,3-dimethyl-5-
Methgin carbonylpyrazole-4-sulfonylisocyaner H,I (5g) was dissolved in 5ml of dry acetonitrile (3ml).
To this was added 0.52 g of 2-amino-4-Schiff LI methoxy 6-methylpyrimidine, and the mixture was stirred at room temperature for 17 hours. Filter and wash the formed crystals,
After each drying, 1.1 g of the target product was obtained. Melting point IJ
Synthesis of 5-157'C-N-((4-difluoromethoxy-6-methylpyrimidin-2-yl)aminocarbonyl-4-ethoxycarbonyl-1-methylpyrazole 5-sulfonamide (compound t!+l35) According to Example 1, 4-ethoxycarbonyl-1-methylpyrazole-5-sulbonyl isocyanate and 2-amino-4-difuro-tetramethyl-6-methylpyrimidine were reacted. The desired product was obtained. Melting point: 152-155°C Example 3 N-1: (4-difluoromethoxy-6-methylpyrimidin-2-yl)aminocarbonyl)-4-ethoxycarbonyl-1-methylpifdu Synthesis of 3-sulfonamide (compound No. 95) According to Example 1, 4-
A Lj-like compound was obtained by reacting ethoxycarbonyl-1-methylpyrazole-3-sulbonylisosialyl-1. with 2-amino-4-dinololomethoxy-6-methylpyrimidine. Melting point: 115-120°C When applying the compound of the present invention as a herbicide, it is generally carried out using a suitable carrier, such as a solid carrier such as clay, curcum, bentonite, or diatom, or water, alcohols (methanol, ethanol, etc.), aromatic Liquid carriers such as hydrocarbons (henzene, toluene, quinolene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (acetic acid, chloride, etc.), acid) amides (dinotylborumamide, etc.) It can be used in combination with "ζ", and if desired, an emulsifier,
By adding dispersants, suspending agents, penetrating agents, spreading agents, stabilizers, etc., it can be put to practical use in the form of liquids, emulsions, wettable powders, powders, and granules.

Examples of formulations of herbicides in which the compound of the present invention is effective are shown below, but the invention is not limited to these.

In the following formulation examples, 1 part means part by weight.

Distribute on a plate Wettable powder Compound of the present invention N [L20 =, 5 (1 part Sieglite Δ -4 [1 part (Kaolin clay: Thetalai 1.1-product name) Tsurupol 5039 -=-2 Part (mixture of nonionic surfactant and anionic surfactant: Toho Chemical (species part name) Carplex (anti-caking agent) Part 2 (white carbon: Shiono Yoshiharu Pharmaceutical ()...; 111 product name)
The above is uniformly mixed and pulverized to form a wettable powder. When used, the above-mentioned hydrating agent is diluted 50 to 50,000 times and sprayed at an amount of active ingredient of 0.005 kg to 10 kg per hectare.

Chichiki Tanemata Wettable powder Compound of the present invention Positive 65゛ ~---75 parts Sea Cry l-
A - 19 parts (Kaolin clay: Sea Cry 1 - Industry brand name) Tsurupol 5039 ------- 2 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical @ Motion Co., Ltd.) Part name) Carplex (anti-caking agent) -4 parts or more (Boyte Carbon: Shionogi & Co., Ltd. 1 Kiku brand name) are uniformly mixed and pulverized (to make a wettable powder).

1 part 1 row J-emulsion Compound of the present invention NO, 65--11 2 parts K
Shinshin −−−−−・−−1 −−−−−−−−−
78 parts Methylformamide ---15 parts Tsurpol 2680' ---5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical (11 parts names) Subsidy amount or per hectare Spray it so that 0.005 parts kg = 1'0.

Distribution box E Flowable compound of the present invention NO, 20-=-25 parts Ageliseal S
-7'IO---10 parts (nonionic surfactant:
Kao "l truss (seed part name), ・ Lunosox 1000 C---0, 5 parts (anionic surfactant 2 Toho Chemical (I...trade name) 1% rhodobol water-
--20 parts (thickener: Lone Boulin product name) water --・-・-
−−−・−・−−−−−−−−−1−・・−44,5
・Mix the above ingredients uniformly to make Lalo'I pull agent.

L plate L Granules: Compound of the present invention 11kL20--------0,
1 part bentonite - 55.0 parts 7 talc - 44.9 parts or more are uniformly mixed and pulverized, then a small amount of water is added and stirred. Mix and knead;
It is granulated using an extrusion granulator and dried to form granules.

Formulation example 6 Granules Compound of the present invention Arashi 95----, 0.5 parts bentonite ------, -55.0 parts talc ---
-・----After uniformly mixing and pulverizing 44.5 parts or more,
Add a small amount of water, mix and knead with stirring, granulate using an extrusion granulator, and dry to form granules.

In addition, the compound of the present invention may be used as a preparation or spray as necessary.
I'6 may be applied in combination with other herbicides, various insecticides, fungicides, synergists, etc.

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

In addition, the compounds of the present invention can be applied to control various weeds in non-agricultural fields such as playgrounds, open spaces, and the edges of walls, in addition to agricultural and horticultural fields such as fields, paddy fields, and orchards. The amount of the applied drug varies depending on the application situation, application, exposure, application method, target grass species, cultivated crops, etc., but in general, the amount of active ingredient is 0.005°
Approximately 10 kg is appropriate.

Next, the usability of the compound of the present invention as a herbicide will be specifically explained in the following test examples.

3 Removal by soil treatment 1° 1° 1 - Effect test 1 iii J 5 cm, width 22 cm 5 depth 5 , Hsu Lihu, a mixture of leafminer, dogfish, and soybean, approximately 1.5C1n
After FjL soil was applied, the amount of active ingredient was uniformly spread over the soil surface in a predetermined ratio.

When spraying, use the hydrating agent in the formulation example above, dilute it with water, and spray it over the entire surface with a small sprayer. i11ν1ik'
4. Remove rice and various weeds after 4 weeks? The effects were investigated according to the following criteria.

The results are shown in Table 4.

Some of the compounds of the invention exhibit selectivity towards certain crops.

Judgment Criteria 5- Weed killing rate 90% or more (almost complete death) 4-
Weed killing rate 70-89% 3- Weed killing rate 40-69% 2- Weed killing rate 20-39% 1- Weed killing rate 5-19% o - Weed killing rate 4% or less (almost ineffective) However, the above killing rate The grass percentage was determined by measuring the weight of above-ground plants in the chemically treated area and above-ground plants in the non-treated area using the following formula.

Nariogi Kari Bifurcated Herbicidal Effect Test Board by Stalk and Leaf Treatment 15cIn
, put sterilized diluvial soil in a plastic box with a width of 22 cm and a depth of 6 cln, and store soybeans, crabgrass, Japanese cypress,
Seeds of Koakaza, Hakidamegiku, Ingarashi, and Suherihyu were sown in spots, and the soil was covered with about 1.5 coats of 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.

For the chemical solution applied to cloth in step 11, the hydrating agent of the formulation example described above was diluted with water and applied with a small sprayer to the entire surface of the stems and leaves of grass. Four weeks after spraying the chemical solution, rice and each (・Ii J((
The herbicidal effect on grass was evaluated according to the criteria for the test month (8
It took a while.

The results are shown in Table 5.

Trial wrinkle l Plant growth k ali for cultivated crops, 1 piece J
(Experiment (grass leaf treatment) Sterilized diluvial soil was placed in a pusosu f-tsuku tube with a length of 15 cans and a width of 22 cm, and the seeds of soybeans, green beans, wheat, and barley were sown in a single pattern. The mixture was covered with soil to a depth of approximately 1.5 cm. When each crop reached the stage of 2 = 3 leaf development, the active ingredients were 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 powder or emulsion of the formulation example described above diluted with water and sprayed over the entire foliage of various crops using a small sprayer. Three weeks after spraying the chemical solution, the growth inhibitory effect and phytotoxicity on various crops were investigated.

The survey measured the length of the above-ground part of each crop and compared it with the untreated plot.

The results are shown in Table 6.

Margins below Table 4 Table 5 Table 6 Control compound A 113 Control compound B 113 0Cl13 β nine N-(dimethylamino)succinamic acid C
,C,C(2-chloroethyl)-1-limethylammonium chloride Patent applicant Nissan Chemical Industries, Ltd. Procedural Amendment 21 (voluntary) ■ Case description 1982 Patent Application No. 18 [i 350℃2 Name of the invention'' Pyrazole sulfonylurea derivative, manufacturing method, and Plant growth regulator or herbicide 3 Relationship with the person making the amendment Case: Patent IQ 1 person Address 101 Kami 1, Chiyoda-ku, Tokyo (1 Nishiki-cho 3 T'I)
ff 7th Ll! ! 14 Roy of the amendment order [J 6 Contents of the amendment (1) The following is additionally inserted below the last line of page 20 of the specification.

[ ” (2) The following is additionally inserted from Table 2 on page 23 of Specification 9JS.

(-) (3) The following is additionally inserted from Table 1 on page 24 of the specification.

(4) The following is additionally inserted between lines 14 and 15 on page 26 of the specification.

"Next, the compounds specifically synthesized according to the above Examples 1 and 2.3 are shown in Table 7 below along with the compound synthesized in Examples 1 and 2.3 (compound 20.65.95).

Below margin

Claims (3)

[Claims] (1) General formula (■): 8 [In the formula, Δ represents a hydrogen atom, a lower alkyl group, a lower alkyl group, a halogen atom, or a J-nyl group which may be substituted with a 2l-+:+ group] . B and D each independently represent a lower alkyl group, a halogen atom, a 21/1.1 group, a lower alkoxy group, a haloalkyl group, an arylalkyl group, a COOR group (
R does not represent a hydrogen atom, a lower alkyl group, an allyl group, a p11pagyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkoxycarbonylalkyl group, or a Hensyl group. ), C0NR,1-2 (1 is a hydrogen atom, a lower alkyl group or a phenyl group, ] I1 is a hydrogen atom or a lower alkyl group, or 1 and 2 are together - (Cll 2) m - (m represents an integer of 4, 5 or 6) -C112CI+20 C1
1, ClI2- or Cl12 ClI2 N-(C
113) indicates C112C112-. ), 5Onlt
3 (n represents an integer of 1 or 2, R3 represents a lower alkyl group, phenyl group or allyl alkyl group.) 3
02 NIIa Rs (l-4 is a hydrogen atom or a lower alkyl group, 175 is a lower alkyl group, or R41
5 are together ゛(-(Cll 2 ) m -(m
indicates an integer of 4, 5 or 6. ) -C112C1
120C112Cll2- or -C112C112N
-(C113)Cll2 Indicates Cll2-. ) or represents a phenyl group optionally substituted with a lower alkyl group, a halogen atom, or a 21-group. E represents a hydrogen atom or a lower alkyl group, 7Jo Q represents an oxygen atom or a sulfur atom, and X represents a hydrogen atom, a C11C11i group,
C1111rl' group, C1li2J or CII
FC1i3 group not shown. y is hydrogen atom-1 lower alkyl group, haloken atom, CF3 group, AlS1-l)'mino group,
3-0Z represents a dialkylamino group, a lower)' group, a 1-1-cy group, or an 0C11F2 group.
, 11 units of NJ trash. ] A virazole sulfonol derivative represented by: (2) General formula (■): 1 [In the formula, a hydrogen atom, a lower atom bar group or a low S&
Even when substituted with a 7-alkyl group, J represents a tjunyl group. B and D each independently represent a hydrogen atom, a lower alkyl group, a halogen atom, a YLJ group, a lower alkokene group, a haloalkyl group, an allyl alkyl group, a GOOR group (1 is a hydrogen atom, a lower alkyl group, an allyl group, a propargyl group) group, lower alkoxyalkyl group, haloalkyl group, lower alkoxycarbonylalkyl group, or Hensyl group.)
, CONRI R2 (12 times is hydrogen atom, 1 person 6
and alkyl hydrogen atom or lower alkyl group, or tt, R
2 together - (Cll 2 > m = (m
indicates an integer of 4, 5 or 6. )-C112C11
2 0 C112 C112- or -C112 C1
12 N- <C113) OH2 Cll2- is not shown. ), SOnln3 (11 represents an integer of 0, 1 or 2, 1cy3 (represents a lower alkyl group, phenyl crystal or allyl alkyl group) 502 NR4 1i5 (
R4 is a hydrogen atom or a lower alkyl group, R5 is a lower alkyl group, or In41?5 together represent -(Cll2)Ill-(m represents an integer of 4, 5 or 6). ) -c, ++2C; 112 0
C112 C112- or -C112C112N-
(C113) C112 Indicates C112-. ) or represents a phenyl group optionally substituted with a lower argyl group, a halogen atom, or a nitro group. ] A pyrazole sulfonyl isocyanate derivative represented by the following formula (Ill): [In the formula, E represents a hydrogen atom or a lower alkyl group. 0 indicates oxygen atom or Saoj Kyoryo, X is hydrogen atom, CI
ICIF group, C II B r group, CIIF2 group or CIIPCF3 group. YiJ represents a hydrogen atom, a lower alkyl group, a halokene atom, 1 or 3 groups, an alkylamino group, a dialkyl)'mino group, a lower alkoxy group, or OCllF2M. X does not represent a nitrogen atom or a Cll group. ] General formula (■) characterized by reacting an aminopyrimidine represented by 4; t -j' i no 1 ~ lysine derivative in an inert organic solvent: represents a phenyl group optionally substituted with an atom, a lower alkyl group, a halogen atom, or a lower alkyl group, a halogen atom, or a phenyl group. B and D are each independently a hydrogen atom, a lower alkyl group, a halokene atom, a nitro group, a lower alkokene group, a haloalkyl group, an arylalkyl group, a COOR group (R is a hydrogen atom, a lower alkyl group, an allyl group, a propargyl group, (Does not indicate lower alkoxyalkyl group, haloalkyl group, lower alkoxycarbonylalkyl group or Hensyl group.)
CONRI R2 (12 plates are hydrogen atoms, lower alkyl groups or phenyl groups, 1 to 2 are hydrogen atoms or lower argyl groups, or RIR2 together are -(
Cll2) m-(m represents an integer of 4, 5 or 6) -Cl12C1120C112C112-
or -C11261f2N-(Cll3)C112
Does not show CI+2-. ), 5Onlze3 (r+ is 0.l
Or, it indicates the integer of 2, and 1 and 3 are lower grade -1' Rukiru story,
Indicates a phenyl group or an allylalkyl group. )SO2N
R41ze5 (R4 is a hydrogen atom or LJ lower alkyl group, R5 is a lower)'alkyl group, or R4R5 together represents -(Cll2)m-(m represents an integer of 4.5 or 6). ) −C112CI+2 0 C1
12Cll2 - Manoko is --Cll2 Cl1
2N-(Cll3)C112C112- is shown. )
In addition, (() is a phenyl group which may be substituted with a lower alkyl group, a halogen atom, or a 2! or 11 group. IL represents a hydrogen atom or a lower alkyl group. 0 represents an oxygen atom or a sulfur atom. , X is a hydrogen atom, Cl1CH
i group, CIIBrF gH2CIf l' 2 J
lll, ] indicates Cl1l'CF3 group. ■ is a hydrogen atom, a lower-grade, halogen atom, C113
group, alkylamino group, dialkylamino group, lower)'
Indicates a 1-oxy group or 0C11F2 g. Z is nitrogen 3
- indicates an atom or a C11 group. ] A method for producing a pyrazole sulfonylurea derivative represented by (3) General formula (■): 8 [In the formula, a phenyl group optionally substituted with a hydrogen atom, a lower alkyl group, a halogen atom, or a di-+co group is shown. B and D are each independently a hydrogen atom, a lower alkyl group, a halogen atom, a 2-1'' group, a lower alkoxy group, a haloalkyl group, an allyl alkyl group, a GOOR group (R is a hydrogen atom, a lower alkyl group, an allyl group) , propakyl group, lower alkoxyalkyl group, haloalkyl group, lower alkoxycarbonylalkyl group or Hensyl group!)
, C0NI+'-'R2' (lze is a hydrogen atom,
a lower alkyl group or a phenyl group, 1 and 2 are hydrogen atoms or a lower alkyl group, or l? ,I? 2 are together ゛(-(C"ll 2) II-(m is 4,
Indicates an integer of 5 or 6. -C112C1120C
112Cll2- or -C112C112N-(Cl
l3) C112C112- is not shown. ), 5Onli3
(n represents an integer of 0.1 or 2, and 1 and 3 represent a lower argyl group, a phenyl group, or an alkyl group). ) SC12NR4R5 (R4 hydrogen atom 'I'-u:
or R5 is a lower alkyl group, or R4R5 together are two k''-(C1l 2 ) m=
(m is an integer of 4, 5 or 6.) -C112C
I+20 Cl12 C112- or -(:l12
Cl12N-(1:II3)C112C112- is not shown. ) or a lower alkyl group, a halogen atom, or a phenyl group which may be substituted with 21.+J) 'J', +4 represents a hydrogen atom or a lower alkyl group t0 t> represents an oxygen atom or sulfur represents an atom, X is a hydrogen atom, CIICIF group, CIIBrF group, CIf F
2 m or CII If indicates a CF3 group. y is a hydrogen atom, (1(class argyl group, halogen atom, C1?3
group, alkylamino group, dialkylamino group, lower alkoxy group or OCCl group. Z is a nitrogen atom or b'
=Li:C11l. ] A plant growth regulator manogoha herbicide comprising one or more pyrazolesulfonylurea derivatives represented by the following as a component.