AU739470B2

AU739470B2 - Herbicidal composition for paddy fields

Info

Publication number: AU739470B2
Application number: AU68526/98A
Authority: AU
Inventors: Kaoru Ikeda; Hisato Suzuki
Original assignee: Rhone Poulenc Agro SA; Rhone Poulenc Agrochimie SA
Current assignee: Bayer SAS
Priority date: 1997-04-16
Filing date: 1998-04-16
Publication date: 2001-10-11
Anticipated expiration: 2018-04-16
Also published as: TW482654B; JP3992782B2; CN1222829A; JPH10287513A; KR20000016699A; AU6852698A; WO1998046079A1

Description

I,

DESCRIPTION

HERBICIDAL COMPOSITIONS FOR PADDY FIELDS [TECHNICAL FIELD] This invention relates to herbicidal compositions, in more detail, to herbicidal compositions for paddy fields which show high herbicidal activity on various species of paddy field annual and perennial weeds with very high safety on rice plants by applying before, at the same time, or after transplantation of rice seedlings.

[BACKGROUND ART] Hitherto, as herbicides for paddy fields, various herbicides have been introduced into practice, and used widely as single component or as mixed formula containing two or more than two active ingredients. However, generally speaking, these herbicides are effective enough on annual weeds, but not enough on perennial weeds. On the other hand, herbicides showing good effect on perennial weeds show insufficient effect on annual weeds, consequently, there are several problems such as appearance of resistant weeds and phytotoxicity on rice plants. In order to expand the herbicidal spectrum and enhance the herbicidal efficacy, it is usually applied to mix two or more than two herbicides showing different herbicidal function.

However, generally speaking, enlargement of efficacy by mixing herbicides are limited to an additive effect, and there has been observed a tendency that the phytotoxicity on rice plants is also increased with the increase of efficacy.

There has been desired the development of herbicides showing high herbicidal effect on various species of paddy field annual and perennial weeds with high safety on rice plants, as well as high effect on weeds which are resistant against sulfonylurea herbicides.

[DISCLOSURE OF THE INVENTION The inventors of the present invention have studied on the development of paddy field herbicides satisfying the said desires above of farmers. By combining several compounds having different herbicidal mechanisms and herbicidal spectra in appropriate ratio, herbicidal compositions controlling various paddy field weeds in wide range and selectively were founded.

These compositions showed unexpectedly low phytotoxicity on rice plants, nevertheless the herbicidal efficacy was increased synergistically and the herbicidal spectrum was expanded by comparing to their single use.

Thus, the herbicidal compositions of the present invention has been completed.

The present invention can supply herbicidal compositions characterized by containing as active ingredient a compound represented by the following formula O Cl CH 3

H

3 C

C

I I N OCH 2 CO /CH 3

CH

3 2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethyl-1H-pyrazol-5-yloxy]-4'methylacetophenone common name Benzofenap, published in the Patent Laid-open No. S62-19402 and one or plural compounds selected from the chemical group consisting of a compound represented by the following formula

COOCH

3

OCH

3

CH

2

SO

2 NHCONH N C

OCH

3 (2) methyl 3 4 ,6-dimethoxypyrimidin-2-yl)ureido]sulfonyl]-o-toluate (common name: Bensulfuron methyl, published in the Patent Laid-open No.

S57-112379 or a compound represented by the following formula

CH

3

CH

3 I

N

/N SO 2 NHCONH

~N

N<OCH

3

N

NN

[(4,6-dimethoxypyrimidin-2-yl)aminocarboyl] -1-methyl-4-(2- -yl)-1 H-pyrazol-5 -sulfonamide common name: Azimsulfuron, published in the Patent Laid-open No. S63-185906) or a compound represented by the following formula (4)

COOC

2

H

5

OH

N'

IH

OCH

3 (4) ethyl 5 3 4 6 -dimethoxypyrimidin-2-yl)ureido]sulfonyl] -1H-i methylpyrazol-4-carboxylate common name Pyrazosulfuron ethyl, published in the Patent Laid-open No. S59-1480 and No. S59-122488) or a compound represented by the following formula

N

Cl

CH

3 N

N

S0 2 NHCONH

OCH

3 1 -(2-chloroimidazo[ 1,2-cg~pyridin-3 -ylsulfonyl)-3-(4,6dimethoxypyrimidin-2-yl)urea common name :Imazosulfuron, published in the Patent Laid-open No. Hl-139582 [BEST MODE FOR CARRYING OUT THE INVENTION The compound being used as active ingredient in the present invention is an already known herbicide per se published in the Patent laidopen No. Sho 62-19402, and the compounds and are also already known herbicides per se. In addition, there have been recognized the same herbicidal effect and safety on rice plant as the herbicidal compositions of the present invention in the other pyrazole type herbicides besides the compound for example, pyrazolate, pyrazoxyphen, etc.

There is not special limit of mixing ratio of the compound with the compound or therefore, it can be variable in the wide range depending on application area, targeting weeds, application time, etc.

Generally speaking, it is preferable to be 0.001-100 weight part, more preferably 0.01-10 weight part of the compound 0.001~100 weigh part, or more preferably 0.01-10 weight part of the compound 0.001-100 weight part or more preferably 0.01-10 weight part of the compound and 0.001-100 weight part or more preferably 0.01-10 weight part of the compound In the case of practical use as herbicide of the compositions of the present invention, the said active ingredient above can be mixed with already known solid or liquid carrier, diluent, surfactant, or other auxiliary agent for formulation, and prepared into a usual formula as agrochemicals such as granules, emulsified concentrate, wettable powder, flowable, dry flowable, etc.

As solid carrier being used for preparation of herbicide, there can be cited, for example, clay represented by kaolinites, montmorillonites, illites, polygroskites, etc., more specifically, pyrophyllite, atapulgite, sepiolite, kaolinite, bentonite, saponite, vermiculite, mica, talc, etc., and other inorganic substances such as gypsum, calcium carbonate, dolomite, diatomaceous earth, calcite, magnesium lime, phosphorus lime, zeolite, silica anhydride, synthetic calcium silicate, etc.; organic substances of vegetable origin such as soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose, etc., synthetic or natural polymers such as coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, dammar gum, etc.; waxes such as carnauba wax, bee wax, etc., or urea and the like.

As suitable liquid carriers, there can be cited, for example, paraffin or naphthene hydrocarbons such as kerosene, mineral oil, spindle oil, white oil, etc.; aromatic hydrocarbons such as xylene ethylbenzene, cumene, methylnaphthalene, etc.; chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene, o-chlorotoluene, etc.; ether such as dioxane tetrahydrofuran, etc.; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone, etc.; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate, etc.; alcohols such as n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol, etc.; ether alcohol such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, etc.; polar solvents such as dimethylformamide, dimethyl sulfoxide, etc. or water.

In addition, surfactant, adhesive, and other auxiliary agents may be used for various purposes such as emulsification, dispersion, wetting, spreading, adhesion, combination, destruction control, stabilization of active ingredients, improvement of fluidity, corrosion proof, etc. of the active ingredients.

As surfactant, there may be used one of any type among nonionic, anionic, cationic, and amphoteric surfactants. Usually nonionic and/or anionic surfactants are used. Examples of suitable nonionic surfactants include polymerization additives of ethylene oxide with higher alcohol such as lauryl alcohol, stearyl alcohol, oleyl alcohol, etc.; polymerization additives of ethylene oxide with alkylphenol, such as isooctylphenol, nonylphenol, etc; polymerization additives of ethylene oxide with alkylnaphthol such as butylnaphthol, octylnaphthol, etc.; polymerization additives of ethylene oxide with higher fatty acids such as palmitic acid, stearic acid, oleic acid, etc.; polymerization additives of ethylene oxide with amine such as dodecylamine, stearic acid amine, etc., higher fatty acid ester of higher alcohol, such as sorbitan, etc. or polymerization additives of ethylene oxide therewith; block polymerization additives of ethylene oxide with propylene oxide, etc.

As suitable anionic surfactant, there can be cited, for example, alkyl sulfate salts such as sodium laurylsulfate, amine salts of sulfuric acid ester of oleyl alcohol, etc.; alkyl sulfonate salts such as sodium dioctyl sulfosuccinate, sodium 2-ethylhexenesulfonate, etc.; arylsulfonate salts such as sodium isopropylnaphthalenesulfonate, sodium methylene bisnaphthalenesulfonate, sodium ligninsulfonate, sodium dodecyl benzenesulfonate, etc.; and the like.

Furthermore, for the purposes of improvement of properties of formula, enhancement of effects, etc., the herbicides of the present invention may be used in combination with polymers and other auxiliary agents such as casein, gelatin, albumin, glue, lignin sulfonate, sodium alginate, gum arabic, xanthun gum, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, polyvinylpyrrolidone, polysaccharide, etc.

The carriers and various auxiliary agents described above can be used alone or in combination with others depending on the types of formula, application site, application purpose, etc.

The contents of active ingredients in the various formulae of the present invention thus prepared may vary widely depending on forms of formulae, and suitable content is within the range of usually 0.01-99 more preferably 0.1-80 by weight.

The formula of wettable powder contains, for example, active ingredients in amount of usually 1-90% by weight, and the remainder may be solid carrier and dispersion wetting agent. If necessary, colloid protection agent, defoaming agent, etc. may be added thereto.

The formula of granules contains, for example, active ingredients in amount of usually 0.01-35 %by weight, and the remainder may be solid carrier and surfactant. The active ingredients may be mixed with solid carrier uniformly, or fixed to or adsorbed on the surface of solid carriers uniformly. The diameter of a granule particle is preferably in the range of about 0.05-3.0 mm, more preferably 0.2-1.5 mm.

The flowable formula contains, for example, active ingredients in amount of usually 0.5-50 by weight, and in addition 3-10 by weight of dispersion wetting agent, and the remainder being water. If necessary, anticorrosive agent, preservative, defoaming agent, etc. may be added thereto.

Appropriate application doses of the composition of the present invention prepared as described above can not be generally determined because of depending on weather conditions, soil conditions, forms of chemical formula, targeting crops, targeting weeds, application time, application ways, etc. Usually, based on the total amount of active ingredients, the application doses are 0.01-1000 kg, more preferably 0.1-100 kg per hectare. Furthermore, a controlling agent with man power saving can be supplied by adding other insecticide, fungicide, plant growth regulator to the compositions of the present invention.

In addition, if necessary, the compositions can be used by mixing at the time of spraying with some other insecticide, fungicide, plant growth regulator, herbicide, fertilizer, etc. Next, some embodiments of the present invention will be explained with Examples.

[EXAMPLES]

Application Example 1 (Flowable formula) Compound 12.0 weight Compound 1.0 weight,% Polyoxyethylene nonylphenyl ether 2.0 weight Sodium dioctylsulfosuccinate 2.0 weight Xanthun gum 0.2 weight Water 82.8 weight The above mixture was pulverized uniformly using a wet ball mill to obtain flowable formula.

Application Example 2 (Granule formula) Compound 6.0 weight Compound 0.06 weight Sodium ligninsulfonate 3.0 weight Sodium alkylnaphthalenesulfonate 1.0 weight Bentonite 30.0 weight Talc 59.94 weight The above mixture was mixed and pulverized, and granulated by the usual methods with a granulator, and dried to obtain granule formula.

Application Example 3 (Wettable powder) Compound 12.0 weight Compound 0.42 weight Sodium lingninsulfonate 3.0 weight Sodium dialkylnaphthalenefulfonate 3.0 weight Kaolin 81.58 weight The above mixture was mixed and pulverized uniformly to obtain wettable powder formula.

Application Example 4 Flowable formula) Compound 12.0 weight Compound 1.7 weight Polyoxyethylene nonylphenyl ether 2.0 weight Sodium dioctylsulfosuccinate 2.0 weight Xanthun gum 0.2 weight Plu 'S

-IU

rn 2'' Water 82.1 weight The above mixture was pulverized with a wet ball mill to obtain flowable formula.

Next, the efficacy of the compositions of the present invention will be described practically with some test examples.

Test Example 1 Effects of dose reduction and enhancement of herbicidal efficacy by mixed soil application) Suitable amounts of paddy field soil and chemical fertilizers were added into a concrete pot with surface of 0.25 m 2 followed by kneading with a suitable amount of water to convert into the state of paddy field.

Three stocks of rice plant seedlings, each one stock being composed of a pair of two seedlings which had been grown in advance in a greenhouse to the stage of two leave, were transplanted into each pot. Afterwards, there were sown predetermined amounts of seeds of Konagi (Monochoria vaginalis), Azena (Lindernia procumbens), Mizuaoi (Monochoria korsakowii), Tamagayatsuri (Cyperus difformis), Kogomegayatsuri (Cyperus iria), respectively, and bulbs of Mizugayatsuri (Cyperus serotinus), and Urikawa (Sagittaria pygmaea) were planted.

On the same day of transplantation, predetermined amount of test compound was applied as wettable formula.

After 30 days from the application of the chemicals, herbicidal efficacy and phytotoxicity on rice plants were assessed. The results are shown in the tables 2, 3, 4 and In these tables, herbicidal efficacy and phytotoxicity on rice plants were assessed based on the criteria as described in the said table 1 below 6 different points from roJ to [5J for the former, and 6 different points from [-J to for the latter.

In addition, fresh weight of each one stock of rice plant including both upper and lower parts from the water surface was determined as index for assess of phytotoxicity.

Test Example 2 Effect of dose reduction and enhancement of herbicidal efficacy by mixed foliar and soil application) In the same methods as the test example 1, test pots were prepared, and predetermined amount of test samples were applied as wettable powder after 10 days from rice transplantation.

The results of herbicidal efficacy and phytotoxicity on rice plant being assessed after 30 days from the application of chemicals are shown in tables 6, 7, 8, and 9.

In these tables, degree of herbicidal efficacy and phytotoxicity are shown in the same way to the criteria shown in the said table 1 below in six different points from ro0 to r5J for the former, and six different points from to for the latter. Same as the test example 1, fresh weight of one stock of rice plant including both upper and lower parts from the water surface was determined as index for assess of phytotoxicity.

Table 1. Criteria for assessment of herbicidal efficacy and phytotoxicit Herbicidal efficacy Point Efficacy ratio 100 4 over 80 and below 100 3 over 60 and below 80 2 over 40 and below 60 1 over 20 and below 40 0 over 0 and below 20 Point Phytotoxicity Degree withered heavy damage medium damage small damage slight damage no damage Table 2. Test example 1 soil application No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp (1)Comp A B C D E F G rice Comp 250 3 3 3 3 3 2 3 500 4 4 4 4 4 3 4 1000 5 5 5 5 5 4 5 Comp 25 3 3 0 4 4 4 5 5 0 5 5 5 5 This 500 25 5 5 5 5 5 5 Invention 500 50 5 5 5 5 5 5 Control 0 0 0 0 0 0 0 A Konagi (Monochoria vaginalis) B Azena (Lindernia procumbens) C Mizuaoi (Monochoria korsakowii) D Tamagayatsuri (Cyperus difformis) E Kogomegayatsuri (Cyperus iria) F Mizugayatsuri (Cyperus serotinus) G Urikawa (Sagittaria pygmaea) Table 3. Test example 1 soil application No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp Comp A B C D E F G rice COMP 250 33 33 3 2 3 500 4 4 4 4 4 3 4- 1000 5 5 5 5 5 4 Camp 15 3 3 0 4 4 4 4 5 5 0 5 5 5 5 This 500 15 555 5 5 5 Invention 500 30 5 5 5 5 5 5 Control 00 00 0 0 0 A :Konagi (Monochoria vaginalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowil) D :Tamagayatsuri (Cyperus difformis) E :Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pygmaea) Table 4. Test example 1 soil application) No. of Dose_(g ai/ha) Herbicidal efficacy Phytotoxicity Sample Camp Comp A B C ID E F IG rice Camp 250 33 33 3 2 3 500 4 4 4 4 4 3 4- 1000 5 5 5 5 5 4 Camp 10.5 3 3 0 3 2 4 4 21 5 5 0 5 4 5 This 500 10.5 5 5 5 5 5 5 Invention 500 21 5 5 5 5 5 5 Control 00 00 0 0 0 A :Konagi (Monochria va'ginalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowil) D :Tamagayatsuri (Cyperus difformis) E :Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pygmaea) Table 5. Test example 1 soil application) No. of Dose (g ai/ha) Herbicidal efficacy -Phytotoxicity Sample Comp Comp A IB IC D E IF G rice CaMP 250 33 3 33 23 500 4 4 4 4 4 3 4 1000 5 5 5 5 5 4 5 Camp 42.5 3 3 0 2 2 4 4 5 5 0 4 4 5 This 500 42.5 5 5 5 5 5 5 Invention 500 85 5 5 5 5 5 5 Control 0 0 0 0 0 0 0- A :Konagi (Monochria va'gin'alis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowli) D :Tamagayatsuri (Cyperus difformis) E :Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pyglnaea) Table 6. Test example 2 foliar and soil application) No. of Dose_(g ailha) Herbicidal efficacy Phytotoxicity sample Comp (i)Comp A B C D E F G rice CaMP 250 22 22 2 13 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp 25 33 02 2 33 4 4 0 4 3 5 This 500 25 55 55 5 5 invention 500 50 5 5 5 5 5 5 Control 0 0 0 0 0 0 0- A :Konagi (Monochoria va'ginalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowil) D :Tamagayatsuri (Cyperus difformis) E Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pygmaea) Table 7. Test example 2 foliar and soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp Comp A B C D E F G rice CaMP 250 2 2 22 2 1 3 500 3 3 3 3 3 2 4- 1000 4 4 4 4 4 3 Camp 15 3 3 702 2 4 2 4 4 0 4 4 5 4+- This 500 15 55 55 5 5 invention 500 30 5 5 5 5 5 5 Control 0 000 007 0 A Konagi (Monochria vag'inalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowil) D :Tamagayatsuri (Cyperus difformis) E Kogomegayatsuri (Cyperus iria) F Mizugayatsuri (Cyperus serotinus) G Urikawa (Sagittaria pygmaea) 17 Table 8. Test example foliar and soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp (1)Comp A B C D E F G rice Comp 250 22 22 2 13 500 3 33 3 3 2 4 1000 4 4 4 4 4 3 5 Comp 10.5 3 3 03 3 43 21 4 4 0 4 4 5 4+- This 500 10.5 5 5 5 5 5 5 Invention 500 21 5 5 5 5 5 5 Control 0 0 0 0 7 0 A Konagi (Monochoria vaginalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowli) D :Tamagayatsuri (Cyperus di! formis) E :Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pygmaea) Table 9. Test example 2 foliar and soil application No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp Comp A B C D E F G rice Comp 250 22 22 2 13 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp 42.5 3 3 702 2 34 4 4 0 3 3 4 This 500 42.5 5 5 5 5 5 5 invention 500 85 5 5 5 5 5 5 Control 0 0 7 7 7 0Y A Konagi (Monochoria vaginalis) B :Azena (Lindernia procumbens) C :Mizuaoi (Monochoria korsakowii) D :Tamagayatsuri (Cyperus di! formis) E :Kogomegayatsuri (Cyperus iria) F :Mizugayatsuri (Cyperus serotinus) G :Urikawa (Sagittaria pygmaea) [EFFECTS OF INVENTION] Based on the results of the test examples described above, it has been elucidated that the compositions of the present invention show clear enhanced effects compared to those of single use of each active ingredient, and that it can control various weeds at very low doses.

Namely, as clearly seen in the test examples described above, there have been observed enlarged herbicidal spectra and enhanced herbicidal efficacy due to synergism being unexpectedly observed in some weeds compared to those of single use of the compounds or and not observed at all any increased phytotoxicity on rice plants.

The application time can be selected optionally in the wide range from pre-transplantation of rice seedlings to the early growth stage of weeds (approximately after 20 days from transplantation however, the highest herbicidal effects can be obtained by applying in the range from pregermination to growing stage of weeds immediately after transplantation to r the 15th day after transplantation).

i From the outstanding effects of the compositions of the present invention, it can be strongly suggested that the compound has increased herbicidal effects on the weeds being resistant against the compounds or Consequently the compositions of the present invention can supply herbicides showing high herbicidal effects on weeds being resistant against sulfonylurea-group herbicides. Thus, this invention is a technique being very useful in agriculture field, and in addition, it can supply compositions being economic and less loading in the environment, by showing outstanding herbicidal effects at low doses of each herbicide.

P.\OPER\Mil\68526-98 233 doc-.21/0I01 18A- Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

The reference to any prior art in this specification is not, and should not be taken as, an acknowledgment or any form of suggestion that the prior art forms part of the common general knowledge in Australia.

a 0*

Claims

1. Herbicidal compositions for paddy fields characterized by containing as active ingredient a compound of 2-[4-(2,4-dichloro-m-toluoyl)-1 ,3- dimethyl- 1H-pyrazol-5 -yloxy] -methylacetophenone characterized by the general formula (1) O CI CH 3 H 3 C 1 NN OCH

2 CO CH

3 GCl 3 and one or plural compound(s) selected from the chemical groupcnitg of a compound of methyl ct-[[ 3 -(4,6-dimethoxypyrimidin-2- yl)ureido]sulfonyl]-o-toluate characterized by the general formula (2) COOCH 3 OCH 3 N CH 2 SONHCONH OCH 3 (2) or a compound of [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- 1-methyl-

4-(2-methyl-2H-tetrazol-5 -yl)-l H-pyrazol-5 -sulfonamide characterized by the general formula CH 3 N N, )CH 3 N S0 2 NHCONH/ N (3) or a compound of ethyl 5-[[3-(4,6-dimethoxypyrimidin-2- yl)ureido] sulfonyl] -1H-i -methylpyrazol-4-carboxylate characterized by the general formula COOC 2 H I OCH 3 'N S0 2 NHCONH CH 3 OCH 3 (4) or a compound of 1 -(2-chloroimidazo [1 ,2-c]pyridin-3-ylsulfonyl)-3-(4,6- dimethoxypyrimidin-2-yl)urea characterized by the general formula P:\OPER\Ma\68526-98 233.doc-21/08101 -21 Cl SONHCONH 2. Herbicidal compositions substantially as hereinbefore described with reference to any one of the examples. 3. A method of controlling weeds in paddy fields by applying to the soil or foliar a herbicidal composition according to claim 1 either before, during, or after transplantation of the seedlings. DATED THIS 21 st day of August, 2001 Rhone-Poulenc Agro 20 by DAVIES COLLISON CAVE Patent Attorneys for the Applicants 9 9* 9 9* 9