JP2008001601A - Herbicide composition with reduced phytotoxicity - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a phytotoxicity reducing agent and a herbicide composition containing the same. <P>SOLUTION: The herbicide composition having reduced phytotoxicity is obtained by combining (a) a herbicidal compound with (b) at least one kind of a substance having a phytotoxicity reducing action selected from the group consisting of a benzisothiazolinone derivative, benzamide derivative, benzothiazole derivative, benzoxazolinone derivative, benzoxazine derivative, Tiadinil (R), isoprothiolane, hexamethylenetetramine, potassium oxalate and a vanillin derivative. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a herbicide composition with reduced phytotoxicity. Specifically, the present invention relates to a herbicide composition with reduced phytotoxicity comprising a compound having herbicidal activity and a specific compound having a phytotoxicity-reducing action.

  Herbicidal benzoylcyclohexadiones are known in several documents (for example, Patent Documents 1 to 3). Many known herbicides are already known (see Non-Patent Document 1).

Although some of these herbicidal active compounds have selectivity for crops, they have a problem that they cause phytotoxicity to crops depending on usage conditions, application scenes, application rates, target crops, and the like. Therefore, in order to suppress such phytotoxicity, search and discovery of a compound having a phytotoxicity reducing action is desired.
WO 98/29406 WO 01/07422 WO 2004/063187 The Pesticide Manual (13th edition, 2003, published by British Crop Protection Council)

  The present inventors have found that the combination shown below reduces the phytotoxicity of the herbicidal active compound on the crop and exhibits the desired herbicidal effect, thereby completing the present invention.

Thus, the present invention
(A) a herbicidal compound;
(B) at least one selected from the group consisting of benzisothiazolinone derivatives, benzamide derivatives, benzothiazole derivatives, benzoxazolinone derivatives, benzoxazine derivatives, thiazinyl, isoprothiolane, hexamethylenetetramine, potassium oxalate and vanillin derivatives. The present invention provides a herbicide composition having a reduced phytotoxicity comprising a combination of compounds.

  Surprisingly, according to the present invention, when the herbicidal compound (a) and the compound (b) are used in combination, the phytotoxic action of the herbicidal compound (a) is reduced by the compound (b). Therefore, even in a crop cultivation area where it has been difficult to apply the herbicidal compound, it is possible to use it. Further, it has been found that the phytotoxicity-reducing action of the compound (b) is novel and extremely useful, which has not been known so far.

  Examples of the herbicidal compounds of (a) include AE198, mesotrione, sulcotrione, benzobicyclone, pyrazolate, benzophenap, pyrazoxifene, oxadiazone, oxadiargyl, oxadichromemeone, anilophos, mefenacet, fentolazamide, diflufenican, bensulfuronmethyl, caffefentrol , Butachlor, pretilachlor, benfrate, cromeprop, dimetamethrin, dimethrin, pyriftalide, pyriminobacmethyl, pyraclonyl, iodosulfuronmethyl, ethoxysulfuron, pyrazosulfuronethyl, pyrimisulfuran, cyclosulfamuron, azimusulfuron, imazosulfuron, Halosulfuron methyl, orthosulfamuron, synosulfuron, metsulfuronme It can be exemplified Le and pyraflufen ethyl.

  The AE198 is represented by the compound name 2- {2-chloro-4- (methylsulfonyl) -3-[(tetrahydrofuran-3-yloxy) methyl] benzoyl} cyclohexane-1,3-dione described in Patent Document 3. Is.

  The compounds other than AE198 are those described in Non-Patent Document 1.

  Among the compounds of (b), examples of benzoisothiazolinone derivatives include 1,2-benzisothiazolin-3-one and its sodium salt, probenazole, and saccharin.

  Examples of benzamide derivatives include phthalimide and benzamide.

  Examples of benzothiazole derivatives include 2-hydroxybenzothiazole.

  An example of a benzoxazolinone derivative is 2-benzoxazolinone.

  Examples of benzoxazine derivatives include 2H-1,4-benzoxazin-3 (4H) -one and isatoic anhydride.

  Examples of vanillin derivatives include vanillin, vanillic acid, vanillyl alcohol, and ethyl vanillin.

  The compound (b) is described in Non-Patent Document 1 or well known in the field of organic chemistry.

  The compound (b) itself has a phytotoxicity-reducing action. In the herbicidal composition with reduced phytotoxicity of the present invention, the mixing ratio of the herbicidal compound (a) and the compound (b) is herbicidal. Although it can be changed within a relatively wide range depending on the kind of the compound, the application time of the composition, the application region, the application method, etc., in general, (b) per 1 part by weight of the herbicidal compound (a) The compound can be used in a proportion of 0.001 to 5 parts by weight, preferably 0.004 to 3 parts by weight.

  The most preferred feature of the herbicide composition with reduced phytotoxicity of the present invention is that it can exhibit a selective herbicidal action between crops and weeds. And by such selective herbicidal action, this composition of this invention can be used between the following plants.

  Genus of dicotyledonous weeds: Sinapis, Lepidimu, Yaemgra Kinutasou (Galium), Stellaria, Akaza Aritasou (Urtica ono) Amaranthus, Amaranthus, Portulaca, Xanathium, Ipomoea, Polygonum, Ambrosia, Noumami fuji, S Potatoes (Solanum), Red peppers (Roripppa), Odorikosou (Lamium), Stag beetles Nunofuguri (Veronica), Datura (Datura), violet pansy (Viola), Chishimaodoro (Galeopsis), poppy (Papaver), knapweed (Centaurea), galinsoga quadriradiata (Galinsoga), toothcup (Rotala), false pimpernel (Lindernia), and the like.

  The genus of dicotyledonous plants: cotton (Gossypium), soybean (Glycine), chard sugar beet (Beta), carrot (Daucus), common bean (Peanus), pea (Pisum), eggplant potato (Solanum) (Linum), sweet potato morning glory (Ipomoe), broad bean nantengagi (Vicia), tobacco (Nicotiana), tomato (Lycopersicon), peanut (Arachis), rapeseed cabbage cabbage (Brassica), aculine c -Melon (Cucumis), pumpkin (Cucurbita), etc.

  The genus of monocotyledonous weeds: Echinochloa, Enokoro Awa (Setaria), Millet (Panicum), Digitaria, Ayugaeri Timothy (Phlum), Strawberry Tuna Suzumenokatabira (Poa), Ushikokesa Tobo Ohishiba Shikokubie (Eleuusine), Dokumugi (Lolium), Swan-growth Inumugi (Bromus), Oats oats (Ovena) (Avena), Cyperus papyrus shichitoui hamasuge (Cyper), Moro-g Konogi (Monochoria), Tentsuki (Fimbristylis), Omodaka Kwai (Sagittaria), Hariy Ku Guwai (Eleocharis), bulrush, Ukiyagura-thick (Scirpus), Paspalum (Paspalum), platypus (Ischaemum), Agrostis (Agrostis), foxtail (Alopecurus), bermudagrass (Cynodon) and the like.

  Genus of monocotyledonous plants: rice (Oryza), corn popcorn (Zea), wheat (Triticum), barley (Hordeum), oats (Ovena), rye (Secale), sorghum (Sorghum), millet (Panicum), sugar cane, Waseobana (Saccharum), pineapple (Ananas), asparagus (Asparagus), leek leek (Allium) and the like.

  Furthermore, the composition of the present invention is not limited to the above plants, and can be applied to other plants as well.

  Further, the composition of the present invention can be used for controlling weeds in perennial plant cultivation, for example, afforestation, ornamental plantation, orchard, vineyard, citrus orchard, nut orchard, and banana cultivation. , Coffee plantation, tea plantation, rubber plantation, Guinea oil palm plantation, cocoa plantation, orchard, hop plantation, etc., and for selective weed control in annual plant cultivation Can be applied for.

  When the composition of the present invention is used for controlling weeds, it can be made into a usual preparation form. Examples of the dosage form include powders, granules, wettable powders, wettable granules, emulsions, flowable (aqueous suspension) preparations, emulsion preparations, jumbo agents, floating granules (water surface spreading agents) and the like. be able to.

  These preparations can be prepared by methods known per se. For example, the present invention includes mixing the herbicidal compound (a) and the compound (b) with a solid or liquid carrier or diluent, and if necessary, a surfactant or other formulation adjuvant. Can be prepared.

Examples of the solid carrier and / or solid diluent that can be used in formulating the composition of the present invention include clay, kaolin, talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acidic clay, activated clay, attapulgous clay, Inorganic substances made from ores such as vermiculite, perlite, pumice, cinnabar, and meteorites;
Synthetic products such as hydrophilic carbon, hydrophobic silica, white carbon such as calcium silicate, synthetic zeolite, titanium dioxide;
Plant organic substances such as soy flour, tobacco powder, corn cob flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose;
Synthetic or natural polymer compounds such as coumarone resin, petroleum resin, alkyd resin, polyalkylene glycol, ketone resin, ester gum;
Waxes such as carnauba wax and beeswax;
Water-soluble substances such as urea, lactose, sucrose, ammonium sulfate and potassium chloride can be exemplified.

Suitable liquid carriers and / or liquid diluents include, for example,
Fats and oils such as coconut oil, rapeseed oil, corn oil, soybean oil, rice bran oil;
Paraffinic or naphthenic hydrocarbon solvents such as kerosene, mineral oil, spindle oil, white oil, normal paraffin, isoparaffin, naphthene;
Aromatic hydrocarbon solvents such as xylene, alkylbenzene, alkylnaphthalene;
Alcohols such as ethanol, benzyl alcohol, isopropanol, cyclohexanol;
Polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, polyethylene glycol;
Ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether;
Ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone, γ-butyrolactone;
Fatty acid methyl esters such as coconut oil fatty acid methyl ester, dimethyl succinate, dibasic acid methyl ester such as dimethyl glutamate and dimethyl adipate, esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate;
Ethers such as dioxane and tetrahydrofuran;
Examples include polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, N-alkylpyrrolidone, water, and the like.

  In addition, for the purpose of emulsifying, dispersing, wetting, spreading, preventing degradation, enhancing efficacy, etc. and / or improving the physical properties of the formulation (controlling disintegration, improving fluidity, preventing freezing, imparting rain resistance, etc.) Surfactants, binders and other adjuvants can be used. As the surfactant that can be used, any type of nonionic, anionic, cationic and zwitterionic compounds can be used, but usually nonionic and / or anionic compounds are used. used. Suitable nonionic surfactants include, for example, sorbitan fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, sucrose fatty acid esters; polyoxyalkylene fatty acid esters, polyoxyalkylene resin acid esters, polyoxyalkylene fatty acid diesters; polyoxy Alkylene castor oil, polyoxyalkylene hydrogenated castor oil; polyoxyalkylene alkyl ether; polyoxyalkylene alkyl phenyl ether, polyoxyalkylene dialkyl phenyl ether, polyoxyalkylene alkyl phenyl ether formalin condensate; polyoxyethylene / polyoxypropylene block polymer, alkyl Polyoxyethylene / polyoxypropylene block polymer ether, alkylphenyl polyoxye Polyoxyalkylene alkylamine, polyoxyalkylene fatty acid amide; polyoxyalkylene benzylphenyl (or phenylphenyl) ether, polyoxyalkylene styrylphenyl or phenylphenyl) ether; polyoxyalkylene ether and ester Type silicon and fluorine-based surfactants.

  Suitable anionic surfactants include, for example, alkyl sulfate salts, polyoxyalkylene alkyl ether sulfate salts, polyoxyalkylene alkyl phenyl ether sulfate salts, polyoxyalkylene benzyl (or styryl) phenyl (or phenylphenyl). Ether sulfate salt, polyoxyethylene / polyoxypropylene block polymer sulfate salt: paraffin (alkane) sulfonate salt, alpha olefin sulfonate salt, dialkyl sulfosuccinate salt, alkylbenzene sulfonate salt, mono or dialkyl naphthalene sulfonate salt, naphthalene sulfonate / formalin condensation Salt, alkyl diphenyl ether disulfonate, lignin sulfonate, polyoxyalkyl Alkyl phenyl ether sulfonate salt, polyoxyalkylene ether sulfosuccinic acid half ester salt; fatty acid salt, N-methyl fatty acid sarcosinate, resin acid salt; polyoxyalkylene alkyl ether phosphate salt, polyoxyalkylene mono- or dialkyl phenyl ether phosphate salt, polyoxy Examples thereof include alkylene benzyl (or styryl) phenyl (or phenylphenyl) ether phosphate salt, polyoxyethylene / polyoxypropylene block polymer phosphate salt; polyacrylate, polycarboxylate and the like.

  Cationic surfactants include alkyl trimethyl ammonium chloride, methyl polyoxyethylene alkyl alkyl ammonium chloride, alkyl N-methyl pyridinium bromide, mono- or dialkyl methylated ammonium chloride, alkyl pentamethylpropylenediamine dichloride, and other ammonium types; alkyl Examples thereof include benzalkonium types such as dimethylbenzalkonium chloride and benzethonium chloride.

  Examples of amphoteric surfactants include betaine types such as dialkyldiaminoethylbetaine and alkyldimethylbenzylbetaine.

  Examples of the binder include bentonite, casein, gelatin, starch, dextrin, lignin sulfonate, alginate, gum arabic, xanthan gum, carboxymethyl cellulose, methyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and the like.

  Examples of other adjuvants include disintegration regulators, antifreezing agents, preservatives, fluidity improvers, antifoaming agents, moisturizing agents, spreading agents, and rain resistance-imparting agents.

  The above carriers, surfactants, binders and various adjuvants can be appropriately used singly or in combination depending on the purpose in consideration of the dosage form of the preparation, application scene, and the like.

  In general, the preparation can contain the herbicidal compound (a) and the compound (b) in a total concentration of 0.1 to 95% by weight, preferably 0.5 to 90% by weight.

  The composition of the present invention can be used as it is or in the form of a preparation for controlling weeds, and can be mixed in a tank at the time of use. Furthermore, other known active compounds, particularly usually It is also possible to add active compounds to be used, such as fungicides, insecticides, plant growth regulators, plant nutrients, soil conditioners, fertilizers and the like.

  The composition of the present invention can be used as it is, in the form of a preparation thereof, or an application form prepared by further diluting from the preparation, for example, a preparation solution for spraying (e.g., ready-to-use solution), emulsion, suspension, It can be used in the form of powder, wettable powder or granule. The thing of these forms can be applied to a paddy field by methods, such as liquid agent watering (watering), spraying (spraying, atomizing), dusting, dusting.

  The composition of the present invention can be used both before and after germination of plants. Moreover, according to this invention, phytotoxicity reduction can be achieved also by applying the compound of (b) before or after application of the herbicidal compound of (a).

  In the present invention, the amount of the composition that can be applied can vary within a substantial range. The application rate can be, for example, in the range of 0.01 to 10 kg / ha, preferably 0.5 to 5 kg / ha as the total amount of the herbicidal compound (a) and the compound (b).

  The excellent effects of the composition according to the present invention will be described more specifically by the following examples. However, the present invention should not be limited to these.

Biological test example and formulation example (test compound)
(A-1): AE198
(B-1): 1,2-benzisothiazolin-3-one (b-2): probenazole (b-3): saccharin Test Example 1 Effect of reducing phytotoxicity (I)
Test method:
The test was conducted in a two-run system. A 500 cm ² pot was filled with light soil, water was added, and rice seedlings (Nipponbare, 2.5 leaf stage) were transplanted. After transplantation, it was in a flooded state. Six days after transplantation, (b-1) was treated in an amount equivalent to 300 g per hectare. After the treatment, 300 g per hectare of the excess drug amount of (a-1) was treated on the same day.

  During the test period, macroscopic observation was performed 16 days after transplantation (0%; no phytotoxicity, 100%; killed), and leaf age was measured 34 days after transplantation and the above-ground weight of paddy rice was measured 35 days after transplantation.

試験例２ 薬害軽減作用効果試験（ＩＩ）
試験方法：
５００ｃｍ^２のポットに軽埴土を充填し、水を加え、水稲の苗（日本晴、２．５葉期）２株を１ポットに移植した。移植後、湛水状態とした。移植２日後、ヘクタール当たり１ｇから２０００ｇ相当の（ｂ−１）を所定のポットに処理した。移植４日後、（ａ−１）の過剰薬量であるヘクタール当たり２５０ｇを処理した。 Test results:

Test Example 2 Drug damage reduction effect test (II)
Test method:
A 500 cm ² pot was filled with light soil, water was added, and two rice seedlings (Nipponbare, 2.5 leaf stage) were transplanted into one pot. After transplantation, it was in a flooded state. Two days after transplantation, (b-1) corresponding to 1 to 2000 g per hectare was treated in a predetermined pot. Four days after transplantation, 250 g per hectare, which was an excessive dose of (a-1), was treated.

During the test period, macroscopic observation (0%; no phytotoxicity, 100%; withering), leaf age and plant height were examined 31 days after transplantation.
Test results:

試験例３ 薬害軽減作用効果試験（ＩＩＩ）
試験方法：
試験は、２連制で行った。５００ｃｍ^２のポットに軽埴土を充填し、水を加え、水稲の苗（日本晴、２．５葉期）を移植した。移植後、湛水状態とした。移植６日後、ヘクタール当たり３００ｇ相当の（ｂ−２）を所定のポットに処理した。処理後、同日、（ａ−１）の過剰薬量をヘクタール当たり３００ｇ処理した。

Test Example 3 Effects of reducing phytotoxicity (III)
Test method:
The test was conducted in a two-run system. A 500 cm ² pot was filled with light soil, water was added, and rice seedlings (Nipponbare, 2.5 leaf stage) were transplanted. After transplantation, it was in a flooded state. Six days after transplantation, (b-2) equivalent to 300 g per hectare was treated in a predetermined pot. After the treatment, 300 g per hectare of the excess drug amount of (a-1) was treated on the same day.

During the test period, macroscopic observation was performed 16 days after transplantation (0%; no phytotoxicity, 100%; killed), and leaf age was measured 34 days after transplantation and the above-ground weight of paddy rice was measured 35 days after transplantation.
Test results:

試験例４ 薬害軽減作用効果試験（ＩＶ）
試験方法：
試験は、２連制で行った。５００ｃｍ^２のポットに軽埴土を充填し、水を加え、水稲の苗（日本晴、２．５葉期）２株を１ポットに移植した。移植後、湛水状態とした。移植２日後、ヘクタール当たり５０ｇあるいは５００ｇの（ｂ−２）及び（ｂ−３）の夫々を所定のポットに処理した。移植４日後、（ａ−１）の過剰薬量であるヘクタール当たり２５０ｇ相当を処理した。

Test Example 4 Drug damage reduction effect test (IV)
Test method:
The test was conducted in a two-run system. A 500 cm ² pot was filled with light soil, water was added, and two rice seedlings (Nipponbare, 2.5 leaf stage) were transplanted into one pot. After transplantation, it was in a flooded state. Two days after the transplantation, 50 g or 500 g of (b-2) and (b-3) per hectare was treated in a predetermined pot. Four days after transplantation, the equivalent of 250 g per hectare, which is an excess dose of (a-1), was treated.

During the test period, macroscopic observation (0%; no phytotoxicity, 100%; withering), leaf age and plant height were examined 31 days after transplantation.
Test results:

製剤例１（押し出し粒剤）
化合物（ａ−１） １重量部、化合物（ｂ−１） ０．２重量部、ナトリウムベントナイト（モンモリロナイト） ３０重量部、リグニンスルホン酸塩 ３重量部及び炭酸カルシウム ６３．３重量部の混合物に、ジアルキルスルホサクシネートナトリウム塩 ０．５重量部、ポリカルボン酸ナトリウム塩 ２重量部を含む水 ２５重量部を加えて良く捏化し、押し出し式造粒機により５００−１７００μｍの粒状とし、８０℃で乾燥し粒剤とした。

Formulation Example 1 (Extruded granules)
To a mixture of 1 part by weight of compound (a-1), 0.2 part by weight of compound (b-1), 30 parts by weight of sodium bentonite (montmorillonite), 3 parts by weight of lignin sulfonate and 63.3 parts by weight of calcium carbonate, Dialkylsulfosuccinate sodium salt 0.5 parts by weight, polycarboxylic acid sodium salt 2 parts by weight of water 25 parts by weight is added and hatched well, made into granules of 500-1700 μm with an extrusion granulator, and dried at 80 ° C. Granules were used.

Formulation Example 2 (Impregnation process)
84.0 parts by weight of clay mineral particles having a particle size distribution of 0.2-0.7 mm are placed in a container-rotating mixer, and 4 parts by weight of compound (a-1) and compound (b-) together with a liquid diluent under rotation. 1) Spray 0.5 parts by weight and add 1.5 parts by weight of white carbon to make fine granules.

Formulation Example 3 (Flowable)
Compound (a-1) 2 parts by weight, Compound (b-1) 0.4 part by weight, propylene glycol 10 parts by weight, polyoxyalkylene tristyryl phenyl ether 5 parts by weight, xanthan gum 1 part by weight, silicone oil emulsion 0.1 After thoroughly stirring a mixture of parts by weight and 81.65 parts by weight of water, the mixture is pulverized with a pulverizer (Dynomill KDL type) to obtain an aqueous suspension preparation.

Claims (4)

(A) a herbicidal compound;
(B) at least one selected from the group consisting of benzisothiazolinone derivatives, benzamide derivatives, benzothiazole derivatives, benzoxazolinone derivatives, benzoxazine derivatives, thiazinyl, isoprothiolane, hexamethylenetetramine, potassium oxalate and vanillin derivatives. A herbicidal composition with reduced phytotoxicity comprising a combination of compounds. (A) the herbicidal compound according to claim 1 is AE198, mesotrione, sulcotrione, benzobicyclone, pyrazolate, benzophenap, pyrazoxifene, oxadiazone, oxadiargyl, oxadichromemephone, anilophos, mefenacet, fentolazamide, diflufenican, bensulfuron methyl , Caffentrol, butachlor, pretilachlor, benfrate, cromeprop, dimethamethrin, dimethrin, pyriftalide, pyriminobacmethyl, pyraclonyl, iodosulfuronmethyl, ethoxysulfuron, pyrazosulfuronethyl, pyrimylsulfan, cyclosulfamuron, azimusulfuron, Imazosulfuron, halosulfuron methyl, orthosulfamuron, sinosulfuron, metsulfuron (B) the compound is 1,2-benzisothiazolin-3-one and its sodium salt, probenazole, saccharin, phthalimide, benzamide, 2-hydroxy, and at least one member selected from the group consisting of methyl and pyraflufenethyl Benzothiazole, 2-benzoxazolinone, 2H-1,4-benzoxazin-3 (4H) -one, isatoic anhydride, thiazinyl, isoprothiolane, hexamethylenetetramine, potassium oxalate, vanillin, vanillic acid, vanillyl The herbicide composition with reduced phytotoxicity according to claim 1, which is at least one selected from the group consisting of alcohol and ethyl vanillin.   As an active ingredient, at least one selected from the group consisting of benzoisothiazolinone derivatives, benzamide derivatives, benzothiazole derivatives, benzoxazolinone derivatives, benzoxazine derivatives, thiazinyl, isoprothiolane, hexamethylenetetramine, potassium oxalate and vanillin derivatives Contains safeners.   4. The safener according to claim 3, wherein the benzoisothiazolinone derivative is at least one selected from the group consisting of 1,2-benzisothiazolin-3-one and its sodium salt, probenazole and saccharin.