JP2011190196A - Herbicidal composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a herbicidal composition that exhibits high herbicidal effects on principal weeds growing in a paddy field and yet is highly safe to a paddy rice plant. <P>SOLUTION: The herbicidal composition comprises as effective ingredients at least one compound selected from the group consisting of compounds represented by general formula (I) [wherein R<SP>1</SP>-R<SP>5</SP>are each H, F, Cl, Br, I, a methyl group or the like; and X is H, a 4-methylbenzoyl group or the like] and salts thereof, and a compound represented by ethyl(RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate or the like. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to one or more compounds selected from the group consisting of 3-phenoxy-4-pyridazinol compound (I) and ethyl (RS) -2-chloro-3- [2-chloro-5- (4-difluoro). Methyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) -4-fluorophenyl] propionate and / or 1- {3-[(4,6 The present invention relates to a herbicidal composition containing -dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] -2-pyridyl} -2-fluoropropyl = methoxyacetate as an active ingredient, and a method of using the herbicidal composition.

  Currently, many herbicides have been put to practical use as paddy field herbicides and are widely used as single agents and mixed agents. However, there are many types of paddy field weeds, and the germination and growth periods of each weed are not uniform. The occurrence is long-term. Therefore, it is very difficult to control all weeds with a single herbicide spray. Therefore, as a herbicide, many kinds of weeds including annual and perennial weeds can be killed, that is, it has a broad herbicidal spectrum and is effective for weeds that have grown, and the herbicidal effect can be maintained for a certain period. In addition, there is a strong demand for the emergence of highly safe drugs in paddy rice.

  On the other hand, a 3-phenoxy-4-pyridazinol derivative is known to have herbicidal activity, and this derivative has a high effect on annual and perennial weeds, but some weeds (for example, main paddy weeds) The effect on a certain log is not necessarily sufficient (Patent Document 1). In addition, a combination example of this derivative and a specific sulfonylurea herbicide (bensulfuron methyl and azimusulfuron) and a combination example of this derivative and a part of a herbicide having a whitening action (for example, pyrazolate) (Patent Documents 2 and 3), but ethyl (RS) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-) is also known. 5-oxo-1H-1,2,4-triazol-1-yl) -4-fluorophenyl] propionate and 1- {3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl) No combination example with sulfamoyl] -2-pyridyl} -2-fluoropropyl methoxyacetate is known.

  Ethyl (RS) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1- Yl) -4-fluorophenyl] propionate (hereinafter compound A, generic name: carfentrazone ethyl) is a known compound, and can be applied simultaneously with other herbicides, if necessary. Examples of herbicides include acetamide herbicides, triazine herbicides, dinitroaniline herbicides, 2,4-D or sulfonylurea herbicides, and specific examples of combined use of compound A and 2,4-D Specific examples of combined use of Compound A and a sulfonylurea herbicide (thifensulfuron methyl) are known (Patent Documents 4 and 5), but with 3-phenoxy-4-pyridazinol derivatives Example is not known.

  1- {3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] -2-pyridyl} -2-fluoropropyl = methoxyacetate (hereinafter compound B, generic name: flucetosulfuron) is It is a known compound and can be applied at the same time as other herbicides if necessary. Examples of other herbicides include carfentrazone ethyl, sulfonylurea herbicides, acetamide herbicides or benzoyl herbicides. Specific examples of combined use of Compound B and carfentrazone-ethyl, specific examples of combined use of Compound B and a sulfonylurea herbicide (azimusulfuron, etc.) are known (Patent Documents 6 to 6). 9) No combination examples with 3-phenoxy-4-pyridazinol derivatives are known.

WO03 / 016286 JP 2004-262939 A JP 2004-262937 A WO90 / 02120 Publication Japanese National Patent Publication No. 08-501797 JP-T-2004-511478 JP 2006-273441 A JP 2007-045805 A Special table 2008-524206 gazette

  In order to improve the above-mentioned problems of conventional herbicides, the present inventors completely control various weeds with a single spray, and have a high level of safety against paddy rice. As a result of continuing the search for a low and safe herbicide, one or more compounds selected from the group consisting of 3-phenoxy-4-pyridazinol derivatives and salts thereof and ethyl (RS) -2-chloro-3- [2- Chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) -4-fluorophenyl] propionate (compound A) and 1- {3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] -2-pyridyl} -2-fluoropropyl = methoxyacetate (Compound B) is blended as an active ingredient As a result, the herbicidal spectrum is expanded and important weeds can be controlled with a smaller amount of active ingredients, resulting in an unexpectedly superior effect (synergistic action) and also causing phytotoxicity to transplanted rice. As a result, the present invention was completed.

  That is, the present invention has the general formula

[Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an isopropyl group, 2 R ¹ , R ² , R ³ , R ^4, and R ⁵ may be a cyclopropyl group or a methoxy group that may be substituted by one chlorine atom, -CH ₂ CH ₂ CH ₂ - to form a group represented by the proviso, ^{R 1} is not hydrogen atom,
X is a hydrogen atom, 4-methylbenzoyl group, 4-morpholinylcarbonyl group, 1-azetidinecarbonyl group, dimethylcarbamoyl group, 1-propanesulfonyl group or 4-methylbenzenesulfonyl group] One or more compounds selected from the group consisting of (hereinafter referred to as Compound (I)) and salts thereof;

  Ethyl (RS) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1- Yl) -4-fluorophenyl] propionate (hereinafter referred to as Compound A) and / or 1- {3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] -2-pyridyl} -2-fluoropropyl = A herbicidal composition containing methoxyacetate (hereinafter referred to as Compound B) as an active ingredient.

The herbicidal composition of the present invention has a broad herbicidal spectrum, and various weeds that are problematic in paddy fields and the like, for example, grass weeds such as Tainubie; Azena, Azepera, Kakashigusa, Mizohakobe, Abnome, Himemisohagi, Konagi, etc. Broad-leaved weeds; Cypridaceae weeds such as Tamagayatsuri, Inuhotarui, Matsubai, Mitsugayatsuri, Krogwai, etc .; It has an unpredictable herbicidal activity (synergistic action) against certain dog fireflies, scallops, and crocodiles, and does not exhibit any harmful phytotoxicity to crops such as rice.
Therefore, weeding and growth of weeds can be suppressed and weeds can be killed with a small amount of active ingredient and the number of uses. The labor required for the control work can be reduced.

  Unless otherwise stated, each term used in the claims and specification of the present application is defined as commonly used in the field of chemistry, as well as WO03 / 016286, WO90 / 02120, and Special Table 2004. This is based on the definition described in Japanese Patent No. 51478.

  The salt of compound (I) is a salt usually used for agricultural chemicals. When an acidic group (for example, carboxy group) is present in the molecule, for example, an alkali metal salt (for example, lithium salt, sodium salt, potassium) Salt, etc.), alkaline earth metal salts (eg calcium salt, magnesium salt etc.) or ammonium salt, preferably sodium salt, potassium salt or calcium salt ammonium salt, more preferably sodium salt And when a basic group (for example, an amino group) is present in the molecule, for example, a salt with an inorganic acid such as sulfate, hydrochloride, nitrate, phosphate, acetate, oxalate, It can be a salt with an organic acid such as succinate, and can be a sulfate, hydrochloride, nitrate or phosphate, preferably a hydrochloride.

  Further, a solvate of compound (I) or a salt thereof is also included in the present invention.

In formula (I) of the present invention,
R ¹ , R ² , R ³ , R ⁴ and R ⁵ are
Independently of each other, is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an isopropyl group, a cyclopropyl group or a methoxy group optionally substituted by two chlorine atoms Or two adjacent groups of R ¹ , R ² , R ³ , R ⁴ and R ⁵ together form a group represented by —CH ₂ CH ₂ CH ₂ —, wherein R ¹ is hydrogen Not atoms
X is
A hydrogen atom, 4-methylbenzoyl group, 4-morpholinylcarbonyl group, 1-azetidinecarbonyl group, dimethylcarbamoyl group, 1-propanesulfonyl group or 4-methylbenzenesulfonyl group.

  Representative examples of compound (I) are shown in Table 1.

In Table 1 above, in R ^{1 to} R ⁵ , “2-cPr” means that R ¹ is a cyclopropyl group, “6-Me” means that R ⁵ is a methyl group, “2-CH ₂ CH ₂ CH ₂ -3 "indicates that R ¹ and R ² together form a trimethylene group, which is attached to the 2- and 3-positions of the phenoxy ring, and" Me " Represents a methyl group, “cPr” represents a cyclopropyl group, “Ph” represents a phenyl group, and “Morp” represents a morpholinyl group.

The compounds in Table 1 are shown below.
(I) -1; 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinol,
(I) -2; 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol,
(I) -3; 6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol,
(I) -4; 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 4-methylbenzenesulfonate,
(I) -5; 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate,
(I) -6: 6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-methylbenzenesulfonate,
(I) -7: 6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 4-morpholine carboxylate,
(I) -8; 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-morpholinecarboxylate,
(I) -9; 6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-morpholinecarboxylate.

  Compound (I) and a salt thereof, Compound A, and Compound B, which are active ingredients of the herbicidal composition of the present invention, are easily produced by those skilled in the art using known techniques. In particular, WO 03/016286, It can be produced according to the description of WO 90/02120 and JP-T 2004-511478 and according to the description.

  The herbicidal composition of the present invention contains at least one compound selected from the group consisting of compound (I) and a salt thereof and compound A and / or compound B as active ingredients. Various weeds, for example, Gramineae weeds such as Tainubie; broad-leaved weeds such as Azena, Azetope, Kakashigusa, Mizohakobe, Abnome, Himeisohagi, Konagi; Herbicidal weeds; and herbicidal activity such as Urikawa, Omodaka, Heramodaka and herbicidal activity against rice.

  The herbicidal composition of the present invention can be used not only in paddy fields, but also in fields, orchards, mulberry fields, and non-agricultural lands.

  The herbicidal composition of the present invention comprises one or more compounds selected from the group consisting of compound (I) and salts thereof and compound A and / or compound B as active ingredients, thereby synergistic herbicidal The synergistic effect is recognized in a wide range of mixing ratios. For example, compound A and / or compound B can be mixed at a ratio of 0.001 to 10 parts by mass with respect to 1 part by mass of compound (I) or a salt thereof to produce a useful herbicide. The mixing ratio is preferably 0.005 to 5 parts by mass, and more preferably 0.01 to 1 part by mass. The herbicidal composition of the present invention produced in this way has a high herbicidal effect by soil treatment or foliage treatment before and / or after germination of weeds.

  In the present invention, one or more compounds selected from the group consisting of compound (I) and a salt thereof and compound A and / or compound B can be used simultaneously or separately with time.

The herbicidal composition of the present invention may be the active ingredient itself, or may be sprayed with the active ingredient itself, or is usually used as a herbicide by mixing with a carrier and other auxiliary agents as required. It can also be prepared and used as a pharmaceutical form, for example, powder, coarse powder, fine granule, granule, wettable powder, emulsion, aqueous suspension, granular wettable powder, oil suspension, paddy thrower . As used herein, a carrier is a synthetic or natural inorganic or organic substance that is mixed in a herbicide to help reach the plant of an active ingredient compound or to facilitate the storage, transport or handling of the active ingredient. obtain.
Suitable solid carriers are, for example, clays represented by the kaolinite group, montmorillonite group, attapulgite group, etc .; talc, mica, foliar, pumice, vermiculite, gypsum, dolomite, diatomaceous earth, magnesium lime, phosphorus lime , Zeolite, hydrous amorphous silicon dioxide, anhydrous calculation, synthetic calcium silicate, kaolin, bentonite, calcium carbonate and other inorganic substances; soy flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose and other plants Organic substances; synthetic or natural polymer compounds such as coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, dammar gum; wax such as carnauba wax, paraffin wax, beeswax Or urea.
Suitable liquid carriers are, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene; carbon tetrachloride, Chlorinated hydrocarbons such as chloroform, trichloroethylene, monochlorobenzene, chlorotoluene; ethers such as dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, and isophorone; ethyl acetate, amyl acetate, ethylene glycol Esters such as acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate; methanol, hexanol, ethylene glycol, diethylene glycol Call, cyclohexanol, alcohols such as benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether, ether alcohols such as diethylene glycol butyl ether; may be or water; dimethylformamide, polar solvents such as dimethyl sulfoxide.

The herbicidal composition of the present invention contains a surfactant for the purposes of emulsification, dispersion, wetting, spreading, binding, disintegration control, stabilizing active ingredients, improving fluidity, preventing rust, promoting absorption into plants, and the like. You can also The surfactant may be ionic or nonionic.
Suitable nonionic surfactants include, for example, sucrose esters of fatty acids, ethylene oxide polymerized adducts of higher aliphatic alcohols such as lauryl alcohol, stearyl alcohol, oleyl alcohol, and ethylene oxide polymerized addition of alkylphenols such as isooctylphenol and nonylphenol. , Ethylene oxide polymerization adducts of alkyl naphthols such as butyl naphthol and octyl naphthol, ethylene oxide polymerization adducts of higher fatty acids such as palmitic acid, stearic acid and oleic acid, mono- or dialkyl phosphoric acids such as stearyl phosphate dilauryl phosphate Ethylene oxide polymerization adducts, ethylene oxide polymerization adducts of higher aliphatic amines such as dodecylamine and stearamide, higher fatty acid esters of polyhydric alcohols such as sorbitan and their oxidation It may be a copolymer of alkylene polymer adduct and ethylene oxide and propylene oxide.
Suitable anionic surfactants are, for example, alkyl sulfate salts such as sodium lauryl sulfate, oleyl alcohol sulfate ester amine salts, dioctyl sulfosuccinate sodium salts, fatty acid salts such as sodium oleate, sodium stearate, isopropyl naphthalene sulfone. It may be an alkyl aryl sulfonate such as sodium acid, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, sodium dodecylbenzene sulfonate.
Suitable cationic surfactants can be, for example, higher aliphatic amines, quaternary ammonium salts, alkylpyridinium salts.

  Furthermore, the herbicidal composition of the present invention has other components such as gelatin, gum arabic, casein, albumin, glue, sodium alginate, polyvinyl alcohol, carboxymethylcellulose for the purpose of improving the properties of the preparation and enhancing the biological effect. Further, it may contain a polymer compound such as methylcellulose and hydroxymethylcellulose, a thixotropic agent such as sodium polyphosphate and bentonite, and other auxiliary agents.

For example, the powder and coarse powder usually contain 0.1 to 25 parts by mass of an active ingredient, and the balance is a solid carrier.
The wettable powder and granular wettable powder contain, for example, usually 1 to 90 parts by mass of an active ingredient, and the balance is a solid carrier and a dispersion wetting agent. If necessary, a protective colloid, a thixotropic agent and an antifoaming agent are used. The agent is added. These preparations are suspended and dispersed in water when stirred in water.
Granules and fine granules contain, for example, usually 0.1 to 35 parts by mass of an active ingredient, and the remainder is mostly a solid carrier. The active ingredient compound is uniformly mixed with the solid carrier, or is fixed or adsorbed uniformly on the surface of the solid carrier, and the particle diameter is usually 0.2 to 1.5 mm.
The emulsion usually contains, for example, 1 to 70 parts by mass of an active ingredient compound, which contains 5 to 30 parts by mass of an emulsifier, the balance being a liquid carrier, and if necessary, a rust inhibitor. Other adjuvants such as are added.
Aqueous suspensions and oil suspensions are prepared by suspending or emulsifying an active ingredient in water or a high-boiling organic solvent using an appropriate surfactant. Etc. are added to maintain the stability over time.
In paddy field throwing agent, the active ingredient is formulated into an appropriate dosage form, for example, powder, granule, tablet, emulsion, bulk tablet, etc., and if necessary, these are packaged in a water-soluble film or container. However, in use, several to several hundreds of these are used as they are in the paddy field.

  Other herbicides may be added to the herbicidal composition of the present invention in order to broaden the herbicidal spectrum, extend the duration of herbicidal effect, or impart an effect on weeds of high leaf age. it can. Herbicides to be blended are, for example, butachlor, pretilachlor, tenylchlor, piributicalbu, mefenacet, fentrazamide, oxadiclomephone, indanophan, fenfentrol, ipfencarbazone, molinate, beniocarb, esprocarb, dimethylpiperate, anilophos, piperophos, butamifos, etopenzail, etopenzail Halohopbutyl, metamihop, phenoxapropethyl, pyriminobacmethyl, pyriftalide, pentoxazone, biphenox, pyraclonyl, oxadiazone, oxadiargyl, pyrazolate, pyrazoxifene, benzophenap, benzobicyclone, mesotrione, tefriltrione, pyrasulfol, Benfresate, Bromobutide, Daimlon, Kumi Ron, Chlomeprop, MCPB, MCP, Bentazone, Cimethrin, Dimetamethrin, ACN, Bensulfuron methyl, Azimusulfuron, Pyrazosulfuron ethyl, Imazosulfuron, Halosulfuron, Ethoxysulfuron, Orthosulfamron, Cyclosulfamlone, Bispyribac Na, It can be penoxsulam, pyrimisulphan, propyrisulfuron, phenoxasulfone or NC-620, preferably pyrazolate, pyrazoxifene, benzophenap, benzobicyclon, mesotrione or tefryltrione.

  When the herbicidal composition of the present invention prepared in various dosage forms in this way is treated with soil before or after germination of weeds in a paddy field, for example, 0.1 g to 1000 g as an active ingredient per 10a Preferably, weeds can be controlled effectively by treating 1 g to 300 g.

  The herbicidal composition of the present invention is treated with soil, foliage or flooding before germination of weeds or within about one month after emergence, using the herbicidal composition of the present invention formulated by a usual method. Can do. Soil treatment includes soil surface treatment, soil admixing treatment, etc., and foliage treatment includes treatment from the top of the plant body, extreme treatment that treats only weeds so as not to adhere to crops, The flooding treatment includes spraying of granules and flowables and irrigation treatment on the water surface.

  In addition, the herbicidal composition of the present invention can be used by mixing with, for example, a plant growth regulator, fungicide, insecticide, acaricide, nematicide or fertilizer.

  In the present invention, one or more compounds selected from the group consisting of the above-mentioned compound (I) and salts thereof, and compound A and / or compound B may be mixed and sprayed as one preparation, Both active ingredients may be sprayed simultaneously without mixing them, or one active ingredient may be sprayed first and the other active ingredient sprayed later. The order of application is arbitrary. Accordingly, the present invention is a method for weeding weeds, comprising one or more compounds selected from the group consisting of compounds represented by general formula (I) and salts thereof, and compounds A and / or B A herbicidal composition containing one or more compounds selected from the group consisting of a compound represented by formula (I) and a salt thereof is sprayed with a herbicidal composition containing the compound represented by formula (I) And simultaneously spraying the herbicidal composition containing the compound represented by Compound A and / or Compound B, or spraying one herbicidal composition and then spraying the other herbicidal composition It also relates to the method. That is, in a herbicidal method in which one or more compounds selected from the group consisting of the compound represented by the general formula (I) and a salt thereof and the compounds A and / or B are used simultaneously or separately over time. is there.

  Although the formulation example and test example of this invention composition are shown below and demonstrated concretely, this invention is not limited to these. In the following formulation examples, “%” indicates mass%.

Formulation Example 1
Wetting agent Compound (I-8) (6.3 parts by mass), Compound A (4.5 parts by mass), Carplex # 80D (manufactured by Shionogi & Co., Ltd., 10 parts by mass), Gohsenol GL05-S (Japan) Synthetic Chemical Co., Ltd., 2 parts by mass), New Coal 291PG (dioctylsulfosuccinate sodium salt, Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd., 5 parts by mass) ), Radiolite # 200 (manufactured by Showa Chemical Industry Co., Ltd., 10 parts by mass) and H fine powder (manufactured by Keiwa Furnace Co., Ltd., 61.7 parts by mass) were sufficiently mixed. The mixture was pulverized with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Enterprise Co., Ltd.), and mixed wettable powder of Compound (I-8) (6.3%) and Compound A (4.5%) Got.

Formulation Example 2
Wetting agent Compound (I-8) (6.3 parts by mass), Compound B (0.6 parts by mass), Carplex # 80D (manufactured by Shionogi & Co., Ltd., 10 parts by mass), Gohsenol GL05-S (Japan) Synthetic Chemical Co., Ltd., 2 parts by mass), New Coal 291PG (dioctylsulfosuccinate sodium salt, Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen Powder (Daiichi Kogyo Seiyaku Co., Ltd., 5 parts by mass) ), Radiolite # 200 (manufactured by Showa Chemical Industry Co., Ltd., 10 parts by mass) and H fine powder (manufactured by Keiwa Furnace Co., Ltd., 65.6 parts by mass) were sufficiently mixed. The mixture was pulverized with an air mill (SK-JET O MIZER model 0101, manufactured by Seishin Enterprise Co., Ltd.), and mixed wettable powder of Compound (I-8) (6.3%) and Compound B (0.6%) Got.

Test example 1
Herbicidal effect of pretreatment for weed generation under flooded conditions Paddy soil was filled in a 1 / 10000a pot, and after seeding, seeds of dog firefly (SCI) were sown and mixed with the surface layer of the soil. In addition, paddy soil was filled in another 1 / 10,000a pot, and after crushing, a dormant awakened Crogwei (ELE) tuber was planted. Furthermore, after filling another 1 / 10000a pot with paddy soil and plucking, 1.8 leaf-old rice (ORY, variety: Nipponbare) was transplanted at a depth of 2 cm. One day after the scraping, the prescribed amount of wettable powder prepared according to Formulation Example 1 was diluted with water and treated with flooded soil. 31 days after drug treatment, the herbicidal effect was determined according to the following criteria. The results are shown in Table 2. In the table, the value (expected value) representing the additive effect when two compounds are mixed according to the Colby formula (Weeds 15, P20-22, 1967) is shown together with the survey results 31 days after the treatment. When the actual experimental result exceeds the expected value, it means a combination having a synergistic effect.
Criterion 0: Growth inhibition rate 0-9%
1: 10-18% growth inhibition rate
2: Growth inhibition rate 19-27%
3: Growth inhibition rate 28-36%
4: Growth inhibition rate 37-45%
5: Growth inhibition rate 46-54%
6: Growth inhibition rate 55 to 63%
7: Growth inhibition rate 64-72%
8: Growth inhibition rate 73-81%
9: Growth suppression rate 82-90%
10: Growth inhibition rate 91-100%

Test example 2
Herbicidal effect of pretreatment for weed generation under flooded conditions Paddy soil was filled in a 1 / 10000a pot, and after seeding, seeds of dog firefly (SCI) were sown and mixed with the surface layer of the soil. In addition, paddy soil was filled in another 1 / 10,000a pot, and after scouring, tubers of Mizugayatsuri (CYP) and Krogwei (ELE) awakened to sleep were planted. Furthermore, after filling another 1 / 10000a pot with paddy soil and plucking, 1.8 leaf-old rice (ORY, variety: Nipponbare) was transplanted at a depth of 2 cm. Five days after the substitution, the prescribed amount of wettable powder prepared according to Formulation Example 2 was diluted in water and treated with flooded soil. 38 days after drug treatment, the herbicidal effect was determined according to the above criteria. The results are shown in Table 3. As in Table 2, the expected values according to the Colby equation are also shown in the table.

Test example 3
Herbicidal effect of weed growing season treatment under flooded condition Paddy soil was filled in a 1 / 10,000a pot, and tubers of Mizugayatsuri (CYP) and Krogwei (ELE) were planted. Eleven days after cleaving (CYP: 1-2 leaf stage, ELE: 3-5 cm), a predetermined amount of wettable powder prepared according to Formulation Example 1 was diluted with water and treated with flooded soil. 21 days after drug treatment, the herbicidal effect was determined according to the above criteria. The results are shown in Table 4. As in Table 2, the expected values according to the Colby equation are also shown in the table.

Test example 4
Herbicidal effect of weed growing season treatment under flooded conditions After paddy soil was filled in a 1 / 10000a pot, and seeded with fireflies (SCI), seeds of Inuta firefly (SCI) were sown and mixed into the surface layer of the soil. In addition, paddy soil was filled in another 1 / 10000a pot, and after crushing, tubers of Krogwei (ELE) were planted. After 14 days of scratching (SCI: 1 to 1.5 leaf stage, ELE: 4 to 6 cm), a predetermined amount of wettable powder prepared according to Formulation Example 2 was diluted with water and treated with flooded soil. 34 days after drug treatment, the herbicidal effect was determined according to the above criteria. The results are shown in Table 5. As in Table 2, the expected values according to the Colby equation are also shown in the table.

Test Example 5
Herbicidal effect of pretreatment of weeds (combination with other herbicides)
After filling paddy field soil into a 1 / 10000a pot and plucking, seeds of Tainubie (ECH) and Inuta firefly (SCI) were sown and mixed into the surface layer of the soil. In addition, paddy soil was filled in another 1 / 10000a pot, and after planting, tubers of Omodaka (SAT), Urikawa (SAP), Mizugayatsuri (CYP), and Krogwei (ELE) were planted. Each pot was sowed after seeding or transplanting and grown in a greenhouse. One day after transplantation, a predetermined amount of wettable powder prepared according to Formulation Example 1 was diluted with water and treated with flooded soil, and 31 days after drug treatment, herbicidal effects were determined according to the above criteria. . The results are shown in Table 6.

Test Example 6
Herbicidal effect of pretreatment of weeds (combination with other herbicides)
After filling paddy field soil into a 1 / 10000a pot and plucking, seeds of Tainubie (ECH) and Inuta firefly (SCI) were sown and mixed into the surface layer of the soil. In addition, paddy soil was filled in another 1 / 10000a pot, and after planting, tubers of Omodaka (SAT), Urikawa (SAP), Mizugayatsuri (CYP), and Krogwei (ELE) were planted. Each pot was sowed after seeding or transplanting and grown in a greenhouse. Five days after transplantation, the prescribed amount of wettable powder prepared according to Formulation Example 2 was diluted with water and treated with flooded soil, and the herbicidal effect was determined according to the above-mentioned criteria after 38 days of drug treatment. . The results are shown in Table 7.

  As is clear from Test Examples 1 to 6, by using a mixed wettable powder prepared by combining Compound (I) and Compound A and / or Compound B, the synergistic effect surpassed expectations for the weeds tested. Compared with the case where each compound was treated with a single use, a higher herbicidal effect was achieved with a smaller dosage and high safety against paddy rice.

  The herbicidal composition of the present invention can be used as an agricultural and horticultural herbicide, and has an unexpected synergistic effect of expanding the herbicidal spectrum and enabling control of important weeds with a smaller amount of active ingredients. In addition, since it does not cause phytotoxicity to crops, it is an excellent herbicide for agriculture and horticulture.

Claims (7)

General formula

[Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an isopropyl group, 2 R ¹ , R ² , R ³ , R ^4, and R ⁵ may be a cyclopropyl group or a methoxy group that may be substituted by one chlorine atom, -CH ₂ CH ₂ CH ₂ - to form a group represented by the proviso, ^{R 1} is not hydrogen atom,
X is a hydrogen atom, 4-methylbenzoyl group, 4-morpholinylcarbonyl group, 1-azetidinecarbonyl group, dimethylcarbamoyl group, 1-propanesulfonyl group or 4-methylbenzenesulfonyl group] And one or more compounds selected from the group consisting of salts thereof and ethyl (RS) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl) -5-oxo-1H-1,2,4-triazol-1-yl) -4-fluorophenyl] propionate and / or 1- {3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] A herbicidal composition containing 2-pyridyl} -2-fluoropropyl methoxyacetate. The compound represented by the general formula (I) is:
6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinol,
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol,
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinol,
6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 4-methylbenzenesulfonate,
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate,
6-chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl) oxy] -4-pyridazinyl 4-methylbenzenesulfonate,
6-chloro-3- (2,3-dihydro-1H-inden-4-yloxy) -4-pyridazinyl 4-morpholinecarboxylate,
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-morpholine carboxylate, or 6-chloro-3-[(5-methyl-2,3-dihydro-1H-indene- The herbicidal composition according to claim 1, which is 4-yl) oxy] -4-pyridazinyl 4-morpholinecarboxylate. The compound represented by the general formula (I) is:
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol,
6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4-methylbenzenesulfonate, or 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinyl 4 The herbicidal composition according to claim 1 or 2, which is a morpholine carboxylate.   The weeding according to any one of claims 1 to 3, wherein the compounding ratio of the compound A and / or the compound B with respect to 1 part by mass of the compound represented by the general formula (I) is 0.001 to 10 parts by mass. Sex composition.   The weeding according to any one of claims 1 to 3, wherein the compounding ratio of the compound A and / or the compound B with respect to 1 part by mass of the compound represented by the general formula (I) is 0.005 to 5 parts by mass. Sex composition.   The weeding according to any one of claims 1 to 3, wherein the compounding ratio of the compound A and / or the compound B with respect to 1 part by mass of the compound represented by the general formula (I) is 0.01 to 1 part by mass. Sex composition.   A herbicidal method in which one or more compounds selected from the group consisting of the compound represented by the general formula (I) and a salt thereof and the compounds A and / or B are used simultaneously or separately over time.