JP2012025721A - Herbicidal composition, and method for controlling weed - Google Patents

Abstract

で示される化合物。
成分（Ｂ）：式（ＩＩ）

で示される化合物。
【選択図】なしA herbicidal composition and a method for controlling weeds are provided.
Weeds can be controlled with a herbicidal composition containing components (A) and (B) as active ingredients.
Component (A): Formula (I)

A compound represented by
Component (B): Formula (II)

A compound represented by
[Selection figure] None

Description

  The present invention relates to a herbicidal composition and a method for controlling weeds.

At present, many herbicides are used, but there are many kinds of weeds to be controlled, and the occurrence is long. Therefore, a herbicide having a high herbicidal effect, a broad herbicidal spectrum, and excellent crop selectivity is desired.
It is known that certain triketone compounds have herbicidal activity (see, for example, Patent Document 1).

JP 2000-178268 A

  An object of the present invention is to provide an excellent herbicidal composition and a method for controlling weeds.

  As a result of studies to find an excellent herbicidal composition and a method for controlling weeds, the present inventor has found that a herbicidal composition containing a compound represented by the following formula (I) and a compound represented by the following formula (II) as active ingredients. The composition (hereinafter referred to as the herbicidal composition of the present invention) can effectively control weeds that are not sufficiently controlled by each compound alone, and also reduces the amount of each compound treated by synergism. The present inventors have found that this is possible and have arrived at the present invention.

で示される化合物。
成分（Ｂ）：式（ＩＩ）

で示される化合物。
［２］ 成分（Ａ）と成分（Ｂ）との重量比が、１：０．００５〜１：５０の範囲である［１］記載の除草組成物。
［３］ 成分（Ａ）と成分（Ｂ）との重量比が、１：０．０５〜１：２５の範囲である［１］記載の除草組成物。
［４］ 成分（Ａ）と成分（Ｂ）との有効量を雑草又は雑草が生育する場所に施用する工程を有する雑草の防除方法。
成分（Ａ）：式（Ｉ）

で示される化合物。
成分（Ｂ）：式（ＩＩ）

で示される化合物。
［５］ 成分（Ａ）と成分（Ｂ）との重量比が、１：０．００５〜１：５０の範囲である［４］記載の雑草の防除方法。
［６］ 成分（Ａ）と成分（Ｂ）との重量比が、１：０．０５〜１：２５の範囲である［４］記載の雑草の防除方法。
［７］ 雑草が生育する場所が、水田又は畑地である［４］〜［６］いずれか一項記載の雑草の防除方法。 That is, the present invention is as follows.
[1] A herbicidal composition containing the component (A) and the component (B) as active ingredients.
Component (A): Formula (I)

A compound represented by
Component (B): Formula (II)

A compound represented by
[2] The herbicidal composition according to [1], wherein the weight ratio of the component (A) to the component (B) is in the range of 1: 0.005 to 1:50.
[3] The herbicidal composition according to [1], wherein the weight ratio of the component (A) to the component (B) is in the range of 1: 0.05 to 1:25.
[4] A method for controlling weeds comprising a step of applying an effective amount of component (A) and component (B) to weeds or a place where weeds grow.
Component (A): Formula (I)

A compound represented by
Component (B): Formula (II)

A compound represented by
[5] The weed control method according to [4], wherein the weight ratio of the component (A) to the component (B) is in the range of 1: 0.005 to 1:50.
[6] The weed control method according to [4], wherein the weight ratio of the component (A) to the component (B) is in the range of 1: 0.05 to 1:25.
[7] The method for controlling weeds according to any one of [4] to [6], wherein the place where weeds grow is a paddy field or a field.

  According to the present invention, weeds can be controlled.

で示される化合物とは、特開２０００−１７８２６８号公報に記載された化合物である。 This invention herbicidal composition contains a component (A) and a component (B) as an active ingredient.
Component (A), ie, formula (I)

Is a compound described in JP 2000-178268 A.

で示される化合物とは、特開２００５−１４５９５８号公報に記載された化合物である。 Component (B), ie formula (II)

Is a compound described in JP-A-2005-145958.

  The herbicidal composition of the present invention contains a component (A) and a component (B). The herbicidal composition of the present invention is usually further added with an inert carrier; and auxiliary agents for preparation such as surfactants, sticking agents, dispersants, stabilizers, etc., and are wettable powder, granular wettable powder, flowable powder, granule. It is formulated into dry flowables, emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules and the like. The total amount of the component (A) and the component (B) is usually 1 to 90% by weight in the herb composition of the present invention.

  Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier.

  Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexane, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg Dioxane, diisopropyl ether), acid amides (e.g., N, N- dimethylformamide, dimethylacetamide), and halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, carbon tetrachloride) and the like.

  Surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylene compounds, polyoxyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohols. Derivatives.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.

The weed control method of the present invention includes a step of applying an effective amount of the component (A) and the component (B) to the weed or a place where the weed grows. The herbicidal composition of the present invention can be used in the weed control method of the present invention. The application method of the herbicidal composition of the present invention includes, for example, a method of treating the foliage of the present herbicidal composition on weeds, a method of treating the herbicidal composition of the present invention on the soil surface where weeds grow, and the present herbicidal composition of paddy field. Examples thereof include a method of treating the surface water, and a method of mixing the herbicidal composition of the present invention with the soil where weeds grow. In the method for controlling weeds of the present invention, component (A) and component (B) are usually used in an amount of 1 to 5000 g, preferably 10 to 1000 g, per 10,000 m ^{2 of} area to control weeds.

  In the present invention, the weight ratio of the component (A) to the component (B) used as the active ingredient is, for example, in the range of 1: 0.005 to 1:50, and in the range of 1: 0.05 to 1:25. Is mentioned.

  In the present invention, weed control in paddy fields, upland fields, orchards, turf fields, etc. where plowing or non-plowing cultivation is performed;

Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), Kin foxtail (Setaria glauca), barnyardgrass (Echinochloa crus-galli), fall panicum (Panicum dichotomiflorum), Texas Pani cam (Panicum texanum), Meriken acne (Brachiaria platyphylla), Alexander glass (Braciaria plantagenea), Surinamegrass (Braciaria decumbens), Sebum sorghum (Sorghum halekeense) Emissions (Andropogon sorghum), bermudagrass (Cynodon dactylon), oats (Avena fatua), darnel (Lolium multiflorum), black grass (Alopecurus myosuroides), downy brome (Bromus tectorum), Arechinochahiki (Bromus sterilis), Hime canary grass (Phalaris minor) , Apera spica-venti, Agropyron repens, Cyperus iria, Cyperus rotundus, Cyperus esculentus or sulyu racea), Amaranthus retroflexus, Amaranthus hybridus, Amaranthus palmi, Sira (Amaranthus palmis), Araanthus palmi (Fallopia convolvulus), Sanaetade (Polygonum scabulum), American Sanaetade (Persicaria pennsylvanica), Harutade (Persicaria vulgaris) ), Japanese knotweed (Fallopia japonica), White-spotted (Chenopodium album), Japanese cypress (America), Japanese pear (Popularum urum) Ipomoea hederacea), Malva American morning glory (Ipomoea hederacea var. integriuscula), beans morning glory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis), Lamium purpureum (Lamium purpureum), henbit (Lamium amplexicaule), cocklebur (Xanthium pensylvanicum), Inukamitsure (Matricaria perforata or inodora), chamomile (Matricaria chamomilla), corn Marigold (Chrysntheumum segetum), Orchardock (Matricaria matricarioides), Ragweed (Ambrosia artemisiifolia), Obraxa (Ambrosia trifida) ), Erigeron canadensis (Erigeron canadensis), mugwort (Artemisia princeps), goldenrod (Solidago altissima), Erigeron bonariensis (Conyza bonariensis), the United States horn Aeschynomene indica (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida Bega Weed (Desmodium tortuosum), white clover (Trifolium repens), Kudu (Pueraria lobata), Caladium pea (Vicia angustifolia), Commelina communis, Camelina benghalensis, Gemula (Gem) lima aparine), chickweed (Stellaria media), wild radish (Raphanus raphanistrum), field sardine (Sinapis arvensis), nazuna (Capella bursa-pasoris) Wild pansies (Viola tricolor), daisies (Papaver rhoeas), forget-me-nots (Myosotis scorpioides), milkweeds (Asclepias syriaca), euphorbia nips C (Chamaesyce nutans), the United States Fuuro (Geranium carolinianum), Netherlands Fuuro (Erodium cicutarium), horsetail (Equisetum arvense) upland weeds and the like;

Ashikaki (Leersia japonica), barnyardgrass (Echinochloa oryzicola), barnyardgrass (Echinochloa crus-galli var. Formosensis), leptochloa chinensis (Leptochloa chinensis), smallflower umbrellaplant (Cyperus difformis), fimbristylis miliacea (Fimbristylis miliacea), Eleocharis acicularis (Eleocharis acicularis), Scirpus ( Sirpus juncoides), Shirapus wallichii, Cyperus serotinus, Kurowai (Eleocharis kuroguwai), Koboga (Bolbochoenus) koshevnikovii), pulp (Schoenoplectus nipponicus), Monochoria (Monochoria vaginalis), false pimpernel (Lindernia procumbens), Abunome (Dopatrium junceum), Rotala indica (Rotala indica), Ammannia multiflora Roxb (Ammannia multiflora), Elatine triandra Schk (Elatine triandra), Choujitade (Ludwigia epilobioides) , Urikawa (Sagitaria pygmaea), Heramodaka (Arisma canaliculatum), Omodaka (Sagitaria trifolia), Hiramshiro (Potamogeton distinctus), Seri Oenanthe javanica), Mizuhakobe (Callitriche palustris), Azetougarashi (Lindernia micrantha), the United States Na (Lindernia dubia), Eclipta prostrata (Eclipta prostrata), Ibokusa (Murdannia keisak), Paspalum distichum (Paspalum distichum), Ezonosayanukagusa (Leersia oryzoides) paddy fields such as weed;

Naganetera phyloxeroides, Frogsbit (Limnobium spongia), Waterfern (Salvinia spp.), Duckweed (Pistia stratiotes), Water pennywort (genus Hydrocotyle spp.) demersum), duckweed (genus Lemna), cabbage carolina, chrome (Hydrilla verticillata), southern naad (Najas guadalupensis), pondwegopongo (Potamogeton) eton illinoensis, Potamogeton pectinatus, etc.), water meal (genus Wolfia), water mill foils (Myriophyllum spicatum, Myriophyllum heterophyllum, etc.)

Mosses, moss, hornworts. Cyanobacteria. Ferns. Suckers of perennial crops (fruits, stones, berries, nuts, citrus, hops, grapes, etc.).

The herbicidal composition of the present invention can be used, for example, in farmland where the following crops are cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbits (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), lily family vegetables (eg, leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American redfish) Etc.), red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricot, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, black beetle, Japanese cypress, Japanese cypress, pine, spruce, yew, elm, cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Nonogusa, Oshionokegusa, Hyoshinokegusa, etc.), Camamoya, Papilio spp.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, safflower, Amanas, switchgrass, miscanthus, kusayoshi, dangiku, kenaf, cassava, willow, etc.), houseplants, etc.

  The above crops include genetically modified crops.

  The herbicidal composition of the present invention has selectivity for paddy rice. Therefore, the herbicidal composition of the present invention is suitable for a paddy field herbicidal composition.

  The herbicidal composition of the present invention can be mixed or used in combination with other herbicides, insecticides, fungicides, plant growth regulators, safeners, fertilizers and the like.

  Hereinafter, the present invention will be described in more detail with reference to Examples such as Reference Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited thereto. In addition, "part" described in an Example means a weight part.

で示される化合物 ４．９４ｇをアセトニトリル５０ｍｌに加えた。１，３−シクロヘキサンジオン１．８０ｇ、トリエチルアミン４．７ｍｌ、アセトンシアンヒドリン０．１５ｍｌを加えて、５０℃で９時間加熱した。反応混合物を減圧下で濃縮し得られた残渣をクロロホルム５０ｍｌに溶解して、３．５%塩酸５０ｍｌで洗浄した。有機相を無水硫酸マグネシウム上で乾燥した。減圧濃縮して得られた残渣をターシャリブチルメチルエーテル５０ｍｌで洗浄した後にアセトンより再結晶化を行い、式（Ｉ）

で示される化合物を２．７６ｇ得た。 Reference production example 1
Formula (III)

Was added to 50 ml of acetonitrile. 1.80 g of 1,3-cyclohexanedione, 4.7 ml of triethylamine, and 0.15 ml of acetone cyanohydrin were added and heated at 50 ° C. for 9 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was dissolved in 50 ml of chloroform and washed with 50 ml of 3.5% hydrochloric acid. The organic phase was dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was washed with 50 ml of tertiary butyl methyl ether and then recrystallized from acetone to obtain a compound of formula (I)

2.76 g of the compound represented by

で示される化合物 ２００ｍｇをトルエン５ｍｌに加え、塩化チオニル０．３ｍｌと触媒量のＮ，Ｎ−ジメチルホルムアミドを加えて１１０℃で1時間加熱した。室温下で冷却後、減圧濃縮して得られた残渣をトルエン５ｍｌに溶解して、フェノール１０７ｍｇと６０％水素化ナトリウム５１ｍｇをＮ，Ｎ−ジメチルホルムアミド５ｍｌ中混合した中に、氷冷下で滴下した。2時間室温下で攪拌した後、氷水１０ｍｌに反応混合物を加え、酢酸エチル２０ｍｌで抽出した。飽和食塩水１０ｍｌで３回洗浄後、無水硫酸マグネシウム上で乾燥した。減圧濃縮して得られた残渣をシリカゲルカラムクロマト精製（酢酸エチル：ヘキサン＝１：２）して、式（III）

で示される化合物を１７１ｍｇ得た。
¹ＨＮＭＲ (ＣＤＣｌ₃)δ［ｐｐｍ］:３．４８(２Ｈ，t,Ｊ=６．９Ｈｚ), ３．６１(２Ｈ，ｔ，Ｊ＝６．９Ｈｚ)，７．２５−７．３４(３Ｈ，ｍ),７．４４−７．４９(２Ｈ，ｍ)，７．７８(１Ｈ，ｄ，Ｊ＝８．０Ｈｚ)，８．１４(１Ｈ,ｄ，Ｊ＝８．０Ｈｚ). Reference production example 2
Formula (IV)

200 mg of the compound represented by the formula was added to 5 ml of toluene, 0.3 ml of thionyl chloride and a catalytic amount of N, N-dimethylformamide were added, and the mixture was heated at 110 ° C. for 1 hour. After cooling at room temperature, the residue obtained by concentration under reduced pressure was dissolved in 5 ml of toluene, and 107 mg of phenol and 51 mg of 60% sodium hydride were mixed in 5 ml of N, N-dimethylformamide and added dropwise under ice cooling. did. After stirring at room temperature for 2 hours, the reaction mixture was added to 10 ml of ice water and extracted with 20 ml of ethyl acetate. The extract was washed 3 times with 10 ml of saturated saline and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 2) to give the formula (III)

171 mg of the compound represented by
¹ HNMR (CDCl ₃ ) δ [ppm]: 3.48 (2H, t, J = 6.9 Hz), 3.61 (2H, t, J = 6.9 Hz), 7.25-7.34 (3H , M), 7.44-7.49 (2H, m), 7.78 (1H, d, J = 8.0 Hz), 8.14 (1H, d, J = 8.0 Hz).

で示される化合物は、例えば、特開２０００−１７８２６８号公報に記載の製造方法により製造できる。 Formula (IV)

The compound shown by can be manufactured by the manufacturing method of Unexamined-Japanese-Patent No. 2000-178268, for example.

Formulation Example 1
An appropriate amount of water is added to the mixture of the following elements and kneaded. The resulting kneaded product is granulated, then dried and sieved to obtain granules.
Component (A) 0.3 part Component (B) 2.0 part Neocol <registered trademark> YSK (dialkylsulfosuccinate ester surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 0.5 part Toxanone <registered trademark> GR31A (polycarboxylic acid type anionic surfactant: manufactured by Sanyo Chemical Industries, Ltd.) 2.0 parts Kunigel <registered trademark> V1 (bentonite: manufactured by Kunimine Industries, Ltd.) 30.0 parts calcium carbonate 65.2 parts

Formulation Example 2
An appropriate amount of water is added to the mixture of the following elements and kneaded. The resulting kneaded product is granulated, then dried and sieved to obtain granules.
Component (A) 0.8 part Component (B) 5.3 parts Matsumoto Microsphere <registered trademark> F-80E (plastic hollow body: manufactured by Matsumoto Yushi Seiyaku Co., Ltd.) 2.4 parts Olphine <registered trademark> E1010 (Nissin Chemical Industry Co., Ltd.) 3.0 parts Toxanone <registered trademark> GR31A (polycarboxylic acid type anionic surfactant: Sanyo Chemical Industries Co., Ltd.) 2.0 parts sodium tripolyphosphate 5.0 parts cellogen <Registered trademark> 7A (Daiichi Kogyo Seiyaku Co., Ltd.) 3.0 parts Kunigel <Registered trademark> V1 (Bentonite: manufactured by Kunimine Kogyo Co., Ltd.) 10.0 parts Calcium carbonate 68.5 parts

Test example 1
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. Sprouted Tainubie (Echinochloa oryzicola) was sown at a depth of about 0.5 cm from the surface of the soil, and water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
Eighteen days after mixing the drug diluent, the herbicidal effect on Tainubier was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 1.

Test example 2
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. Shirapus juncoides seeds were sown on the surface of the soil, and water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
Fourteen days after mixing of the drug diluent, the herbicidal effect on the firefly was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 2.

Test example 3
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. A soil mixed with seeds of Azena (Lindernia pyxidaria L.) was put on the surface of the soil. Water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
27 days after mixing the drug diluent, the herbicidal effect on Azena was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 3.

<Test Example 4>
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. On the surface of the soil was put seeds of Monochori vaginalis. Water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
31 days after mixing the drug diluent, the herbicidal effect on the oak was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 4.

<Test Example 5>
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. Germinated urikawa (Sagitaria pygmaea Miq.) Was placed on the surface of the soil. Water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
31 days after mixing the drug diluent, the herbicidal effect on Urikawa was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 5.

<Test Example 6>
A plastic pot (diameter 6 cm x depth 7 cm) was filled with soil to a depth of about 5 cm. Water was put into this pot and scraped. This was left for 3 days. On the surface of the soil, a germinated sedge (Cyperus serotinus Rotb.) Was placed. Water was poured into the pot to a depth of about 1 to 2 cm from the surface of the soil.
2 mg of each of the component (A) and the component (B) is dissolved in 4 mL of acetone containing 2% (W / V) of Tween <20> (surfactant: manufactured by MP Biomedicals), and the whole amount is dissolved with water. The drug dilution solution was obtained by diluting to 20 mL.
A predetermined amount of each drug diluent was mixed with water accumulated in the plastic pot.
Eighteen days after mixing the drug diluent, the herbicidal effect on the scallop was observed. The herbicidal effect was evaluated by an index of 0 to 100 (0: no action to 100: complete killing). The results are shown in Table 6.

Claims (7)

A herbicidal composition containing component (A) and component (B) as active ingredients.
Component (A): Formula (I)

A compound represented by
Component (B): Formula (II)

A compound represented by   The herbicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is in the range of 1: 0.005 to 1:50.   The herbicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is in the range of 1: 0.05 to 1:25. A method for controlling weeds comprising a step of applying an effective amount of component (A) and component (B) to weeds or a place where weeds grow.
Component (A): Formula (I)

A compound represented by
Component (B): Formula (II)

A compound represented by   The method for controlling weeds according to claim 4, wherein the weight ratio of component (A) to component (B) is in the range of 1: 0.005 to 1:50.   The method for controlling weeds according to claim 4, wherein the weight ratio of component (A) to component (B) is in the range of 1: 0.05 to 1:25.   The method for controlling weeds according to any one of claims 4 to 6, wherein the place where the weeds grow is a paddy field or a field.