AU6852698A - Herbicidal composition for paddy fields - Google Patents
Herbicidal composition for paddy fields Download PDFInfo
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- AU6852698A AU6852698A AU68526/98A AU6852698A AU6852698A AU 6852698 A AU6852698 A AU 6852698A AU 68526/98 A AU68526/98 A AU 68526/98A AU 6852698 A AU6852698 A AU 6852698A AU 6852698 A AU6852698 A AU 6852698A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Description
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 A
-/
2 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 (1) O C1 CH 3
H
3 C C1 N
OCH
2 CO
CH
3
CH
3 (1) 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 (2):
COOCH
3
OCH
3 N
CH
2
SO
2 NHCONH N~
OCH
3 (2) methyl c-[[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 (3):
CH
3
CH
3 N N
SO
2 NHCONH
N
OCH
3 N N __ CH 3 N (3) 4 [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(2 methyl-2H-tetrazol-5-yl)-1H-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 OCH3 N, N NN N SO 2 NHCONH
CH
3
OCH
3 (4) ethyl 5-[[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonyl]-1H-1 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 (5): N Cl
CH
3 N S0 2 NHCONH /
OCH
3 (5) 1-(2-chloroimidazo[1,2-c]pyridin-3-ylsulfonyl)-3-(4,6 dimethoxypyrimidin-2-yl)urea ( common name : Imazosulfuron, published in the Patent Laid-open No. H1-139582).
5 [BEST MODE FOR CARRYING OUT THE INVENTION] The compound (1) being used as active ingredient in the present invention is an already known herbicide per se published in the Patent laid open No. Sho 62-19402, and the compounds (2), (3), (4) and (5) 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 (1), for example, pyrazolate, pyrazoxyphen, etc. There is not special limit of mixing ratio of the compound (1) with the compound (2), (3), (4), or (5), 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 (2), 0.001-100 weigh part, or more preferably 0.01-10 weight part of the compound (3), 0.001-100 weight part or more preferably 0.01-10 weight part of the compound (4), and 0.001-100 weight part or more preferably 0.01~10 weight part of the compound (5). 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, usr- 6 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, 0-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
-
'Z7 >7Z 'U I 7 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
>~US
8 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. P'U S.
9 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 (1) 12.0 weight % Compound (2) 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. 7' 10 Application Example 2 ( Granule formula) Compound (1) 6.0 weight % Compound (3) 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 (1) 12.0 weight % Compound (4) 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 (1) 12.0 weight % Compound (5) 1.7 weight % Polyoxyethylene nonylphenyl ether 2.0 weight % Sodium dioctylsulfosuccinate 2.0 weight % Xanthun gum 0.2 weight % r U S '71 11 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 ( 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 5. 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 19 12 different points from [0] to [5] for the former, and 6 different points from [-j to [++++j 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 Example2 (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 [0] to [5] for the former, and six different points from [-j to [++++j 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.
13 Table 1. Criteria for assessment of herbicidal efficacy and phytotoxicity Herbicidal efficacy Phytotoxicity Point Efficay ratio%) Pint Degree 5 100 ++++ withered 4 over 80 and below 100 +++ heavy damage 3 over 60 and below 80 ++ medium damage 2 over 40 and below 60 + small damage 1 over 20 and below 40 +/- slight damage 0 over 0 and below 20 - no damage Table 2. Test example 1 ( soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp (1) Comp (2) A B C D E F G rice COmp (1) 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 (2) 25 3 3 0 4 4 4 4 50 5 5 0 5 5 5 5 +/ This 500 25 5 5 5 5 5 5 5 Invention 500 50 5 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) 14 Table 3. Test example 1 ( soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp (1) Comp (3) A B C D E F G rice Comp (1) 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 (3) 15 3 3 0 4 4 4 4 + 30 5 5 0 5 5 5 5 + This 500 15 5 5 5 5 5 5 5 Invention 500 30 5 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) 15 Table 4. Test example 1 ( soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp (1) Comp (4) A B C D E F G rice Comp (1) 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 (4) 10.5 3 3 0 3 2 4 4 +/ 21 5 5 0 5 4 5 5 +/ This 500 10.5 5 5 5 5 5 5 5 Invention 500 21 5 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 5. Test example 1 ( soil application ) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity Sample Comp (1) Comp (5) A B C D E F G rice Comp (1) 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 (5) 42.5 3 3 0 2 2 4 4 85 5 5 0 4 4 5 5 +/ This 500 42.5 5 5 5 5 5 5 5 Invention 500 85 5 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) 16 Table 6. Test example 2 ( foliar and soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp (1) Comp (2) A B C D E F G rice Comp (1) 250 2 2 2 2 2 1 3 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp (2) 25 3 3 0 2 2 3 3 50 4 4 0 4 3 5 5 +/ This 500 25 5 5 5 5 5 5 5 invention 500 50 5 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 7. Test example 2 ( foliar and soil application) No. of Dose (g ai/ha) Herbicidal.efficacy Phytotoxicity sample Comp (1) Comp (3) A B C D E F G rice Comp (1) 250 2 2 2 2 2 1 3 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp (3) 15 3 3 0 2 2 4 2 + 30 4 4 0 4 4 5 4 +/ This 500 15 5 5 5 5 5 5 5 invention 500 30 5 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) 17 Table 8. Test example ( foliar and soil application) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp (1) Comp (4) A B C D E F G rice Comp (1) 250 2 2 2 2 2 1 3 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp (4) 10.5 3 3 0 3 3 4 3 21 4 4 0 4 4 5 4 +/ This 500 10.5 5 5 5 5 5 5 5 Invention 500 21 5 5 5 5 5 5 5 Control 0 0 0 0 0 0 0 A : Konagi (Monochoria vaginaiis) 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 9. Test example 2 ( foliar and soil application ) No. of Dose (g ai/ha) Herbicidal efficacy Phytotoxicity sample Comp (1) Comp (5) A B C D E F G rice Comp (1) 250 2 2 2 2 2 1 3 500 3 3 3 3 3 2 4 1000 4 4 4 4 4 3 5 Comp (5) 42.5 3 3 0 2 2 3 4 85 4 4 0 3 3 4 5 +/ This 500 42.5 5 5 5 5 5 5 5 invention 500 85 5 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) 18 [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 (2), (3), (4) or (5), 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 pre germination to growing stage of weeds ( immediately after transplantation to the 15th day after transplantation). From the outstanding effects of the compositions of the present invention, it can be strongly suggested that the compound (1) has increased herbicidal effects on the weeds being resistant against the compounds (2), (3), (4) or (5). 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.
Claims (5)
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]-4'-methylacetophenone characterized by the general formula (1) : o Cl CH 3 H 3 C C1 I N OCH
2 CO CH3 CH 3 and one or plural compound(s) selected from the chemical group consisting of a compound of methyl a-[[3-(4,6-dimethoxypyrimidin-2 yl)ureido]sulfonyl]-o-toluate characterized by the general formula (2): COOCH
3 OCH 3 N CH 2 SO 2 NHCONH OCH 3 (2) 20 or a compound of [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl
4-(2-methyl-2H-tetrazol-5-yl)-lH-pyrazol-5-sulfonamide characterized by the general formula (3): CH 3 OCH 3 N N SO 2 NHCONH OCH3 NN N N CH3 (3) or a compound of ethyl 5-[[3-(4,6-dimethoxypyrimidin-2 yl)ureido]sulfonyl]-1H-1-methylpyrazol-4-carboxylate characterized by the general formula (4) COOC 2 H
5 OCH3 N N SO 2 NHCONH CH 3 OCH 3 (4) or a compound of 1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6 dimethoxypyrimidin-2-yl)urea characterized by the general formula (5): 21 N Cl CH 3 SO2NHCONH N OCH 3 (5)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9-99439 | 1997-04-16 | ||
JP9943997A JP3992782B2 (en) | 1997-04-16 | 1997-04-16 | Herbicide composition for paddy field |
PCT/JP1998/001749 WO1998046079A1 (en) | 1997-04-16 | 1998-04-16 | Herbicidal composition for paddy fields |
Publications (2)
Publication Number | Publication Date |
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AU6852698A true AU6852698A (en) | 1998-11-11 |
AU739470B2 AU739470B2 (en) | 2001-10-11 |
Family
ID=14247451
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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AU68526/98A Expired AU739470B2 (en) | 1997-04-16 | 1998-04-16 | Herbicidal composition for paddy fields |
Country Status (6)
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JP (1) | JP3992782B2 (en) |
KR (1) | KR20000016699A (en) |
CN (1) | CN1222829A (en) |
AU (1) | AU739470B2 (en) |
TW (1) | TW482654B (en) |
WO (1) | WO1998046079A1 (en) |
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KR20030026623A (en) * | 2001-09-26 | 2003-04-03 | 안현기 | portable light |
TWI327462B (en) | 2002-01-18 | 2010-07-21 | Sumitomo Chemical Co | Condensed heterocyclic sulfonyl urea compound, a herbicide containing the same, and a method for weed control using the same |
JP2010070578A (en) * | 2010-01-05 | 2010-04-02 | Rhone Poulenc Yuka Agro Kk | Method for controlling paddy field weed |
Family Cites Families (3)
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JPS62212309A (en) * | 1986-03-14 | 1987-09-18 | Nissan Chem Ind Ltd | Herbicide composition |
JP2786258B2 (en) * | 1989-06-16 | 1998-08-13 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Herbicide composition |
JP3024855B2 (en) * | 1992-03-16 | 2000-03-27 | 三共株式会社 | Paddy field herbicidal composition |
-
1997
- 1997-04-16 JP JP9943997A patent/JP3992782B2/en not_active Expired - Lifetime
-
1998
- 1998-04-16 CN CN98800482.8A patent/CN1222829A/en active Pending
- 1998-04-16 TW TW87105939A patent/TW482654B/en active
- 1998-04-16 AU AU68526/98A patent/AU739470B2/en not_active Expired
- 1998-04-16 KR KR1019980710302A patent/KR20000016699A/en not_active Application Discontinuation
- 1998-04-16 WO PCT/JP1998/001749 patent/WO1998046079A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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TW482654B (en) | 2002-04-11 |
CN1222829A (en) | 1999-07-14 |
KR20000016699A (en) | 2000-03-25 |
WO1998046079A1 (en) | 1998-10-22 |
AU739470B2 (en) | 2001-10-11 |
JP3992782B2 (en) | 2007-10-17 |
JPH10287513A (en) | 1998-10-27 |
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