WO1998030564A1 - Sulfonamide derivatives - Google Patents

Abstract

The present invention relates to novel sulfonamide derivatives and in particular to novel sulfonamide derivatives of formula (1), their use and composition as agriculturally suitable herbicides, wherein: R?a, Rb, Rc¿, E, X, Y and Z are the same as defined in the detailed description of the present invention.

Description

SULFONAMIDE DERIVATIVES

BACKGROUND OF THE INVENTION Field of the Invention The present invention relates to novel sulfonamide derivatives or in particular to novel sulfonamide derivatives of the following formula (1), and their use and composition as agriculturally suitable herbicides.

wherein :

R^a represents hydrogen; halogen; oxycarbonyl substituent; aminocarbonyl substituent; Cι ~Cβ alkyl group; Cι ~C₃ mono- or polyhalloalkyl group; Ci ^~C₃ alkoxy group; G C mono- or polyhalloalkoxy group; nitro group; G ~C₃ alkylthio group; Cι —C₃ polyhalloalkylthio group; Cι ~C₃ alkylsulfonyl group; Cι ~C polyhalloalkylsulfonyl group; cyano group; carboxy group; Cι ~C₄ alkoxycarbonyl group; C₃~C alkoxyalkoxycarbonyl group; aminosulfonyl group; formyl group; G ~0. alkylcarbonyl group; or C —C₃ mono- or polyhalloalkylcarbonyl group;

R^b represents hydrogen; halogen; O ~C₆ alkyl group; substituted Ci ~C_ή halloalkyl group in which one to three substituents are halogen atoms; Ci — Cβ alkylcarbonyl group ; G ~C₆ alkoxycarbonyl group; phenyl group; or phenoxy group;

R represents hydrogen; halogen; Cι ~C₆ alkyl group; C₃ -C_fi cycloalkyl group; or Ci ~ C₃ halloalkyl group;

E represents N or CH; X, Y and Z independently represent hydrogen; halogen; hydroxy group; carboxy group; G ~G. alkyl group; G ~C6 mono- or polyhalloalkyl group; Ci ~ Cβ alkoxy group; G ~ Cβ mono- or polyhalloalkoxy group; phenyl group; substituted phenyl group in which one to five substituents are selected from halogen, nitro group, G ~C₃ alkyl group, and Ci ~C₃ mono- or polyhalloalkyl group; or G ~ C₆ alkylthio group. Further, Y and Z may be combined together to form 3 ~ 7 membered rings, or combined with one or more hetero atoms selected from nitrogen, oxygen and sulfur to form 3 ~ 7 membered heterocycles.

Description of the Prior Art

Utilization of the compounds with herbicidal activities in order to control the weed growth is an important element in the modern agricultural industry.

Many compounds have been used for the purposes of controlling weed growth. However, the herbicide with a broader herbicidal activities, plant-specific growth suppression, environmentally-friendly property, and cost-effectiveness is still in demand.

The quinoline-based compounds with the above formula (1) has not been reported as of the filing of this application.

SUMMARY OF THE INVENTION

Therefore, the objective of the present invention is to provide novel sulfonamide derivatives having very prominent herbicidal activities toward rice and wheat and also possess a good selectivity for annual and perennial weeds.

Another objective of the present invention is to provide herbicidal compositions containing said derivatives as active ingredients. Detailed Description of the Invention

The present invention is related to novel sulfonamide derivatives of the following formula (1).

wherein : R^a, R^b, R^c, E, X, Y and Z are the same as defined the above formula (1), respectively.

The preferred sulfonamide derivatives of the formula (1) according to the present invention, are as follows:

In case where from the above R^a is hydrogen, halogen, G ~Cβ alkyl group, or G ~C₃ mono- or polyhalloalkyl group; R^b is hydrogen, halogen, G ~ Cβ alkyl group, substituted G — Cβ halloalkyl group in which one to three substituents are selected from halogen atoms, G ~ C₃ alkylcarbonyl group, or G ~ Cβ alkoxycarbonyl group; R^c is hydrogen, halogen, G ~ Cβ alkyl group, or G ~ C₃ halloalkyl group; E is N or CH; X, Y and Z are independently selected from hydrogen, halogen, G ^~-Cβ alkyl group, G ~Cβ mono- or polyhalloalkyl group, G ~Cβ alkoxy group, or G ~Cβ mono- or polyhallo alkoxy group. The sulfonamide derivatives according to the present invention may be prepared by the following reaction schemes 1 and 2. Further, some sulfonamide derivatives may be easily prepared by a person having ordinary skill in the art to which the this invention pertains.

The following reaction scheme 1 is a schematic diagram showing a process for preparing sulfonamide derivatives of the above formula (1) as a target product by means of reacting a compound of the formula (2) and a compound of the formula (3). [Scheme 1]

c

( ) ( 3 )

wherein : R^a, R^b, R^c, E, X, Y and Z are the same as defined in the above formula (1), respectively.

Another process for preparing the sulfonamide derivatives of the above formula (1) as a target product is a reaction of a compound of the formula (2) with a compound of formula (3) in the presence of the general organic bases such as pyridine or methyl pyridine. It is preferred to use pyridine as base in this case. Further, its preparation process is illustrated in the following reaction Scheme 2. [Scheme 2]

( 2 ) ( 3 )

wherein : R^a, R^b, R^c, E, X, Y and Z are the same as defined in the above formula (1), respectively.

A process for preparing the sulfonamide derivatives of the above formula (1) according to the present invention is explained in more detail as set forth hereunder. The compounds of the formula (2) is reacted with compounds of the formula (3) in the molar equivalence or excess to obtain sulfonamide derivatives of the above formula (1) as a target product.

Such reaction is carried out in an inert solvent such as acetonitrile, N,N- dimethylformamide, N-methyl-2-pyrrolidinone, or tetrahydrofuran. It is preferred to use a acetonitrile. The reaction is carried out in the presence of base. Generally the base are used in one to five molar ratio compared with the compounds of the above formula (2). The reaction temperature is kept at -78 °C ~ room temperature. It is heated if necessary.

The completion of reaction is assumed when no more compound of the above formula (2) remains, or a target compound of the above formula (1) is produced in high yield.

The target compounds can be easily obtained by evaporation and then filter, or work-up, etc. A pure compound may be obtained by extraction using nonaqueous organic solvent such as dichloromethane and purification. In addition, the sulfonamide derivatives of the above formula (1) can be easily obtained by purification techniques such as recrystallization or chromatography.

The compounds of the above formula (2) as raw materials are known compounds listed in literatures and may be easily prepared by the known process [US Patent No. 4,954,163, US Patent No. 5,010,195, EP No. 244,948, WO 96/01826 and WO 96/01828].

Also the compounds of the above formula (3) as raw materials are prepared by the following schemes. The following amination of quinolinecarbonyl chloride, a known compound listed in US Patent No. 4,497,651, is disclosed in Organic Syntheses Coll. vol. IV 819(1963). [Scheme 3]

wherein : R^a, R^b and R^c are the same as defined in the above formula (1), respectively.

The quinolinecarbonyl chloride compounds of the above formula (4) may be easily prepared using carboxy compounds of the following formula (5). Further, the above carboxy compounds are prepared by known oxidation of the compounds of the following formula (6). Such oxidation of the methyl group is carried out by the method mentioned in US Patent No. 4,715,889, and explained as shown in the following scheme 4. [Scheme 4]

Oxidant

wherein : R^a, R^b and R^c are the same as defined in the above formula (1), respectively.

Other process for preparing the compounds of the above formula (3) is as shown in scheme 5. The process includes an introduction of a nitro group into the quinoline compound [Ronne E. and Grivas S., Heterocycles 36(1), 101 -105(1993)] and reduction thereafter [Gershon H., Clarke D. D. and Gershon M, Monatsh Chem. 127(3), 331 -337(1996)]. [Scheme 5]

wherein : R^a, R^b and R^c are the same as defined in the above formula (1), respectively. In addition, the compounds of the above formula (3) may be prepared by the method disclosed in literature [Zh. Org. Khim 26(10), 2191 -2198(1990); Chem. Lett 1996, (12), 1077-1078].

Also, the compounds of the above formula (3) may be easily prepared by the prior art using the known compounds listed in GB Patent No. 1,424,359, US Patent Nos. 4,511,393, 4,632,696, 4,717,416 and 4,715,889 etc.

The sulfonamide derivatives according to the present invention are sufficiently tolerant on most broadleaf and grass crops such as rice, soybeans, cotton and wheat. Such derivatives may also be useful for pre-emergent control of grassy weeds in said crops. The sulfonamide derivatives of the present invention may be applied for instance in the form of wettable powder, dust, granules, solutions, suspensions or emulsifiable concentrates etc.

To prepare the above formulations, either solid carrier or liquid carrier can be used.

As the liquid carrier, water, toluene, xylene, petroleum eyher, oils, acetone, methyl ethyl ketone, cyclohexanone, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol or glycerine etc. can be used. It is preferred to use water for a diluent of said concentrate.

As the solid carrier, talc, clay, silica, chalk, siliceous earth, lime, calcium carbonate, bentonite, cotton seed hulls, wheat powder, soy powder, sawdust, lignin etc. can be used.

Surfactants, including cationic, anionic and nonionic surfactants, can be employed in the instance case. As the surfactants, diethanolammonium raurylsulfate, alkyl arylsulfonate (such as calcium dodecylbenzenesulfonate), alkylphenol-alkylene oxide adduct, alcohol-alkylene oxide adduct, soaps, alkyl naphthalenesulfonate salt, sulfosuccinate salt, sorbitol ester tert-ammonium salt, polyethylene glycol ester or alkyl phosphate ester salt etc. can be used.

Also, the herbicidal composition according to the present invention may be formulated with other herbicides, insecticides, fungicides, plant growth regulators or fertilizers. The contents of the sulfonamide derivatives of the formula (1), while varying depending on the formulations, is usually from 0.001 to 98 wt%, preferably from 0.01 to 90 wt%.

Prior to the use, the compositions are diluted with an inert carrier, such as water etc. Further, the compositions are applied by means of common techniques, such as sprayer, granulator etc.

The sulfonamide derivatives according to the present invention are highly active as pre-emergent or post-emergent herbicides or plant growth regulants. When applied in high concentration, said compounds become nonselective herbicide. On the other hand, when applied in low concentration, said compounds become a herbicide with crop selectivity. The possible candidates for the application are corn, wheat, oat, rice, soybean, cotton, etc. However, the compounds as represented by the above formula (1) under the present invention may have varying herbicidal activity, plant- selectivity, and control spectrum, depending on the type of substituents.

The term of "weed control" under the present invention means suppression activity of the natural growth. However, the activities herein vary depending on the type of a plant, environment, or application method. In general, the compounds represented by the above formula (1) under the present invention should be applied during the pre-germination stage or before the full-growth for the optimum result.

The application amount of the sulfonamide derivatives represented by the above formula(l) is from 0.01 to 10 kg/ha. High concentrates are used for non-selective activity where as low concentrates are used for the plant- selective activity.

The present invention is explained in more detail by the following examples but is not limited by these examples.

EXAMPLE 1: Preparation of 5,7-dimethyl-N-(3,7-dichloroquinolin-8-yl)-l,2,4- triazolo [1 ,5-c] pyrimidin-2-sulf onamide

To a stirring solution of 8-amino-3,7-dichloroquinoline(212 mg) in anhydrous tetrahydrofuran(20 ml) cooled to -78 ^°C, 2.5M of n-BuLi(0.44 ml) was added drop wise. After stirring for 20 min at -78 ^°C, a solution of 5,7- dimethyl-l,2,4-triazolo[l,5-a]pyrimidin-2-sulfonyl chloride(500 mg) in anhydrous tetrahydrofuran(10 mL) was slowly injected. The solvent was removed under the reduced pressure, and water was poured into the residue and filtered. The water phase was washed with ethyl ether, acidified to pH 3 with 5% hydrochloric acid, and then extracted three times with dichloromethane. The separated organic layers were dried on MgS0 , filtered, and concentrated under reduced pressure. The crude solid was recrystallized using mixture solvent of dimethyl sulfoxide and ethyl ether for crystallization to give 80 mg of the target compound, m.p. : 248 ~ 250 ^°C

Η-NMR(DMSO-d₆) ppm : δ 2.6(s, 3H), 2.7(s, 3H), 7.4(s, 1H), 7.8(d, 1H), 8.0(d,

1H), 8.1(d, 1H), 8.6(d, 1H), 11.0(br, 1H)

EXAMPLE 2: Preparation of 5,7-dimethyl-N-(7-chloroquinolin-8-yl)-l,2,4- triazolo [1 ,5-c] pyrimidin-2-sulf onamide

The target compound was prepared in the same procedure as described in the example 1, 8-amino-7-chloroquinoline in place of 8-amino-3,7- dichloroquinoline.

EXAMPLE 3: Preparation of 5,7-dimethyl-N-(7-fluoroquinolin-8-yl)-l,2,4- triazolo [1 ,5-c] pyrimidin-2-sulf onamide

The target compound was prepared in the same procedure as described in the example 1, 8-amino-7-fluoroquinoline in place of 8-amino-3,7- dichloroquinoline.

EXAMPLE 4: Preparation of 5,7-dimethoxy-N-(7-fluoroquinolin-8-yl)-l,2,4- triazolo [1 ,5-c] py rimidin-2-sulf onamide

The target compound was prepared in the same procedure as described in the example 1, 8-amino-7-fluoroquinoline in place of 8-amino-3,7- dichloroquinolihe.

EXAMPLE 5: Preparation of N-(7-fluoroquinolin-8-yl)-7-fluoro-5-methoxy- l,2,4-triazolo[l,5-c] py r imidin-2-sulf onamide

To a stirring solution of 8-amino-7-fluoroquinoline(5.4 g) and 2- chlorosulfonyl-7-fluoro-5-methoxy-l,2,4-triazolo[l,5-c]pyrimidine(3.0 g) in anhydrous acetonitrile(20 ml), anhydrous pyridine(0.91 ml) and anhydrous dimethyl sulfoxide(0.16 ml) were added. After stirring for 2 hours at room temperature, a reaction mixture was poured into the mixture solution of water (200 ml) and dichloromethane(80 ml). The mixture was stirred for

1 hour. The separated organic layers were dried on MgS0 , filtered and concentrated under reduced pressure. The concentrated residue was purified by flash column chromatography on silica gel to give the target compound as a solid phase.

EXAMPLE 6: Preparation of N-(7-fluoroquinolin-8-yl)-7-fluoro-5-ethoxy-l,2,4- triazolo [1 ,5-c] py rimidin-2-sulf onamide The target compound was prepared in the same procedure as described in the example 5, 2-chlorosulfonyl-7-fluoro-5-ethoxy-l,2,4-triazolo[l,5- c]pyrimidine in place of 2-chlorosulfonyl-7-fluoro-5-methoxy-l,2,4- triazolo [1 ,5-c] py rimidine.

EXAMPLE 7: Preparation of N-(7-fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4- triazolo[l,5-c]pyrimidin-2-sulfonamide

To a stirring solution of N-(7-fluoroquinolin-8-yl)-7-fluoro-5-methoxy- l,2,4-triazolo[l,5-c]pyrimidin-2-sulfonamide(0.6 g) in dimethyl sulfoxide(20 ml), the solution of potassium methoxide(0.24 g) in anhydrous ethanol(2.4 ml) was added. After stirring for 1 hour, acetic acid(5 ml) was added to a reaction mixture. A reaction mixture was poured into dichloromethane(400 ml) and washed six times with water (200 ml). The separated organic layers were dried on MgS0₄, filtered and concentrated under reduced pressure to give the titled compound.

EXAMPLE 8: Preparation of 8-amino-3,7-dichloroquinoline

To a stirring solution of 3,7-dichloroquinolin-8-carbonyl chloride(6.0 g) in dichloromethane(50 ml), the solution of sodium azide(1.8 g) dissolved in water (20 ml) at 0^°C was slowly added. After stirring for 4 hours at room temperature, the separated dichloromethane layer were washed with water(20 ml) and concentrated under reduced pressure. The residue was dissolved in ethyl ether(50 ml) and refluxing 2 hours. The ethyl ether was concentrated under reduced pressure. To the residue was added to the acetonitrile(50 ml), water(20 ml) and 5% hydrochloric acid(l ml) with the refluxing for 2 hours. The reaction mixture was basified with sodium hydroxide solution and then concentrated under reduced pressure. The residue solid was dried in vacuum and recrystallized using mixture solvent of ethyl ether and n-hexane to give 1.3 g of the target compound as a yellow solid.

Η-NMR(CDC ) ppm : δ 8.57(s, 1H), 7.94(s, 1H), 7.33(d, 1H), 6.92(d, 1H),

5.2(brs, 2H)

EXAMPLE 9 : Preparation of Wettable Powder

N-(7-Fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4-triazolo[l,5-c]pyrimidin-2- sulf onamide 80 wt%

Sodium alkylnaphthalenesulfonate 2 wt%

Sodium ligninsulfonate 2 wt% Synthesized amorphous silica 3 wt%

Kaolinite 13 wt%

The ingredients are blended, hammer-milled until all the solids are essentially under 50 --m, re-blended, and packaged. EXAMPLE 10 : Preparation of Wettable Powder

N-(7-Fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4-triazolo[l,5-c]pyrimidin-2- sulf onamide 20 wt% Sodium alkylnaphthalenesulfonate 4 wt%

Sodium ligninsulfonate 4 wt%

Low viscous methyl cellulose 3 wt%

Attapulgite 69 wt%

The ingredients are thoroughly blended, hammer-milled until all the solids are essentially under 100 ^, re-blended, sifted through a U.S.S. No. 50 sieve(0.3 mm opening) and packaged.

EXAMPLE 11 : Preparation of Low Strength Granule N-(7-Fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4-triazolo[l,5-c]pyrimidin-2- sulfonamide 1 wt%

N,N-dimethylformamide 9 wt%

Attapulgite granule(U.S.S. 20 ~ 40 sieve) 90 wt%

The ingredients are dissolved in the solvent and the solution is sprayed upon de-dusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 12 : Preparation of Aqueous Suspension

N-(7-Fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4-triazolo[l,5-c]pyrimidin-2- sulfonamide 40 wt%

Polyacrylic acid concentrate 0.3 wt%

Dodecylphenol polyethylene glycol ether 0.5 wt%

Disodium phosphate 1 wt% Monosodium phosphate 0.5 wt%

Poly vinyl alcohol 1.0 wt%

Water 56.7 wt%

The ingredients are blended and ground together in a sand mill to produce particles essentially under 5 n.

EXAMPLE 13 : Preparation of Solution

N-(7-Fluoroquinolin-8-yl)-5,7-dimethoxy-l,2,4-triazolo[l,5-c]-pyrimidin-2- sulfonamide 5 wt% Water 95 wt%

The ingredients are dissolved in water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 14 : Preparation of Wettable Powder N-(7-Fluoroquinolin-8-y l)-5,7-dimethoxy-l ,2,4-triazolo [1 ,5-c] pyrimidin-2- sulf onamide 40 wt%

Dioctyl sodium sulfosuccinate 1.5 wt%

Sodium ligninsulfonate 3 wt%

Low viscous methyl cellulose 1.5 wt% Attapulgite 54 wt%

The ingredients are thoroughly blended, passed through an air mill, in order to produce an average particle size under 15 fln, re-blended, sifted through a U.S.S. No. 50 sieve(0.3 mm opening) and packaged.

EXAMPLE 15 : Preparation of Granule

Wettable powder of Example 14 15 wt%

Gypsum 69 wt%

Potassium sulfate 16 wt% The ingredients are blended in a rotating mixer, and water sprayed on to accomplish granulation. When most of the material has reached the target range of from 1.0 to 0.42 cm(U.S.S. No. 18 ~ 40 sieve), the granules are removed, dried, and screened. Oversized material is additionally crushed to the target range.

The herbicidal effect of the compounds of the present invention was tested by the greenhouse test. The method is as follows. TEST 1 : Pre-emergence test To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with 5 parts by weight of acetone, 1 part by weight of alkylaryl polyglycol ether as emulsifier was added and the solution diluted with water to the desired concentration. Seeds of the test plants are shown in normal soil and, after 24 hours, watered with the preparation of the active compound.

It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants was rated in % damage in comparison to the development of the untreated control. The figures denote : 0% : no action(like untreated control) 20% : slight effect 70% : herbicidal effect 100% : total destruction

In this test, the active compounds(l) according to the preparation examples exhibited a better herbicidal activity against mono- and dicotyledon weeds. TEST 2 : post-emergence test

To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with 5 parts by weight of acetone, 1 5 part by weight of emulsifier was added and the solution diluted with water to the desired concentration.

Test plants which had a height of 5 ~ 15 cm were sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of i o the spray liquid was so chosen that the particular amounts of active compound desired were applied in 2,000 / of water/ ha. After three weeks, the degree of damage to the plants was rated in % damage in comparison to the development of the untreated control. The figures denote : 15 0% : no action(like untreated control) 20% : slight effect 70% : herbicidal effect 100% : total destruction

In this test, the active compounds(l) according to the preparation 0 examples exhibited a better herbicidal activity against mono- and dicotyledon weeds.

TEST 3 : Fresh-water treatment paddy submerged test

A plastic pot having a surface of 60 cm² or 140 cm²was filled with a small 5 amount of fertilizer, after then, the sterilized paddy soil of puddled state at the depth of 5 cm.

Seeds of barnyard grass, umbrella plant, dayflower, monochoria, tooth cup, smart weed, and bulrush et al. and perennial nutrition body of flat-sedge and arrowhead et al., were seeded or planted in surface layer of soil, and pre- germinated rice with 2 ~ 3 leaves was transplanted one root per pot at the depth of 2 cm.

After planting, the pot was watered for a day at the depth of 2 cm and the manufactured herbicide was spot-treated on the plant in manner similar to the field condition(4 mg/pot).

Two weeks after treatment, herbicidal effect was measured by the same survey standard as that for field condition.

It is understood that the above examples are illustrative but not limitation of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art.

The following Table 1 represents pre- and post-emergence herbicidal effect of active ingredients of the present invention.

The plant species employed in these tests were selected from the following :

SORBI(common sorghum), ECHCG(Barnyardgrass), DIGSA(Large crabgrass, PANDI(Fall panicum), AESIN(Indian jointvetch),

XANSI(Cocklebur), CAGHE(Bindweed), ECHOR(Barnyardgrass),

SCPJU(Bulrush), MOOVA(Monochoria), CYPSE(Flat sedge), SAGPY(Arrow head).

Table 1. Primary Screening(Herbicide)

Claims

CLAIMS What is claimed is:

1. A sulfonamide derivative of the following formula (1):

5 wherein :

R^a represents hydrogen; halogen; oxycarbonyl substituent; aminocarbonyl substituent; G ~ Cβ alkyl group; G — G mono- or polyhalloalkyl group; G ~C₃ alkoxy group; G ~C mono- or polyhalloalkoxy group; nitro group; G ~ Q, alkyl thio group; G — O I o polyhalloalkylthio group; G ~ C₃ alkylsulfonyl group; G — G polyhalloalkylsulfonyl group; cyano group; carboxy group; G — G alkoxycarbonyl group; G~ G alkoxyalkoxycarbonyl group; aminosulfonyl group; formyl group; G ~ G alkylcarbonyl group; or G ~ G mono- or polyhalloalkylcarbonyl group; 15 R^b represents hydrogen; halogen; G — Cβ alkyl group; substituted

G ~ Cβ halloalkyl group in which one to three substituents are selected from halogen atoms; G ~ Cβ alkylcarbonyl group; G ~ Cβ alkoxycarbonyl group; phenyl group; or phenoxy group;

R^c represents hydrogen; halogen; G ~ Cβ alkyl group; G~ Cβ 0 cycloalkyl group; or G — G halloalkyl group;

E represents N or CH;

X, Y and Z independently represent hydrogen; halogen; hydroxy group; carboxy group; G — Cβ alkyl group; G ~ Cβ mono- or polyhalloalkyl group; G ^~ Cβ alkoxy group; G — Cβ mono- or polyhalloalkoxy group; phenyl group; substituted phenyl group in which one to five substituent are selected from halogen, nitro group, G ~ C3 alkyl group, and G — C3 mono- or polyhalloalkyl group; or G ~ Cβ alkylthio group. Further Y and Z may be combined together to form 3 - 7 membered rings, or combined with one or more hetero atoms selected from nitrogen, oxygen and sulfur to form 3 - 7 membered heterocycles.

2. The sulfonamide derivative according to claim 1, wherein

R^a is hydrogen, halogen, G ~ Cβ alkyl group, or G ~ mono- or polyhalloalkyl group;

R^b is hydrogen, halogen, G — Cβ alkyl group, substituted G — Cβ halloalkyl group in which one to three substituents are selected from halogen atoms, G ~ G alkylcarbonyl group, or G ~ Cβ alkoxycarbonyl group;

R^c is hydrogen, halogen, G ~ Cβ alkyl group, or G — G halloalkyl group;

E is N or CH; X, Y and Z are independently selected from hydrogen, halogen;

G — Cβ alkyl group, G ~Cβ mono- or polyhalloalkyl group, G ~ Cβ alkoxy group, or G ~ Cβ mono- or polyhallo alkoxy group.

3. Herbicidal compositions comprising the sulfonamide derivative of the following formula (1):

wherein : R^a, R^b, R^c, E, X, Y and Z are the same as defined in the above claim 1, respectively.

4. A plant growth regulant comprising the sulfonamide derivative of the following formula (1) as an active component :

wherein : R^a, R^b, R^c, E, X, Y and Z are the same as defined in the above claim 1, respectively.