JP5130774B2 - Herbicidal composition - Google Patents

Description

  The present invention relates to a herbicidal composition.

Currently, many herbicides are commercially available and used (see, for example, Non-Patent Document 1). However, there are many types of weeds to be controlled, and the generation is long-lasting, so the herbicidal effect is higher and wider. There is a need for herbicides that have a herbicidal spectrum, have long-lasting effects, and do not cause phytotoxicity problems on crops.
Crop Protection Handbook 2003 (Crop Protection Handbook, Vol. 89 (2003), Meister Publishing Company, ISBN: 1-892829-06-1)

  An object of the present invention is to provide a technique for controlling a wide range of weeds, which has a higher herbicidal effect and does not cause a problem of phytotoxicity to crops.

で表される化合物とを有効成分として含有する除草用組成物（以下、本発明組成物と記す。）。
［発明２］
水田又は畑地において雑草を防除するための除草用組成物であり、有効成分として
[ａ]１−（２−クロロイミダゾ［１，２−ａ］ピリジン−３−イルスルホニル）−３−（４，６−ジメトキシピリミジン−２−イル）ウレアと、
[ｂ]式（II）で表される化合物とを、[ａ]と[ｂ]との重量比が１：０．１〜１：１０の範囲で含有することを特徴とする除草用組成物。
［発明３］
[ａ]と[ｂ]との重量比が１：０．５〜１：２の範囲であることを特徴とする前項２記載の除草用組成物。
［発明４］
水田又は畑地において雑草を防除する方法であり、同時に若しくは併用して
[ａ]１−（２−クロロイミダゾ［１，２−ａ］ピリジン−３−イルスルホニル）−３−（４，６−ジメトキシピリミジン−２−イル）ウレアと、
[ｂ]式（II）で表される化合物とを雑草が生育している若しくは生育する場所の土壌又は雑草に施用することを特徴とする方法。
［発明５］
水田又は畑地において雑草を防除する方法であり、同時に若しくは併用して
[ａ]１−（２−クロロイミダゾ［１，２−ａ］ピリジン−３−イルスルホニル）−３−（４，６−ジメトキシピリミジン−２−イル）ウレアと、
[ｂ]式（II）で表される化合物とを、[ａ]と[ｂ]との重量比が１：０．１〜１：１０の範囲で雑草が生育している若しくは生育する場所の土壌又は雑草に施用することを特徴とする方法。
［発明６］
[ａ]と[ｂ]との重量比が１：０．５〜１：２の範囲であることを特徴とする前項５記載の方法。
［発明７］
水田又は畑地において雑草を防除するための除草用組成物の有効成分としての、
[ａ]１−（２−クロロイミダゾ［１，２−ａ］ピリジン−３−イルスルホニル）−３−（４，６−ジメトキシピリミジン−２−イル）ウレアと、
[ｂ]式（II）で表される化合物との組み合わせの使用。 As a result of intensive studies in such a situation, the present inventors have reached the present invention.
That is, the present invention provides the following inventions and the like.
[Invention 1]
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

A herbicidal composition comprising a compound represented by formula (I) as an active ingredient (hereinafter referred to as the present composition).
[Invention 2]
A herbicidal composition for controlling weeds in paddy fields or upland fields, as an active ingredient
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] A herbicidal composition comprising a compound represented by formula (II) in a weight ratio of [a] to [b] in the range of 1: 0.1 to 1:10. .
[Invention 3]
3. The herbicidal composition according to item 2 above, wherein the weight ratio of [a] to [b] is in the range of 1: 0.5 to 1: 2.
[Invention 4]
It is a method to control weeds in paddy fields or upland fields, and at the same time or in combination
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] A method comprising applying a compound represented by the formula (II) to soil or weeds where weeds grow or grow.
[Invention 5]
It is a method to control weeds in paddy fields or upland fields, and at the same time or in combination
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] a compound represented by the formula (II), wherein the weight ratio of [a] to [b] is in the range of 1: 0.1 to 1:10, and where weeds grow or grow Applying to soil or weeds.
[Invention 6]
6. The method according to item 5 above, wherein the weight ratio of [a] to [b] is in the range of 1: 0.5 to 1: 2.
[Invention 7]
As an active ingredient of a herbicidal composition for controlling weeds in paddy fields or upland fields,
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Use of a combination with a compound represented by the formula (II).

  According to the present invention, it can be applied at a low dose in paddy fields or upland fields, and a wide range of weeds can be controlled.

で表され、一般名をイマゾスルフロン（imazosulfuron、CAS RN 122548-33-8）とする化合物（以下、化合物１と記す。）であり、特開昭64-38091号公報に記載される公知の製造法により製造することができ、化合物１を含有する市販の製剤を入手することもできる。式（II）で表される化合物（以下、化合物２と記す。）は、特開2004-123690号公報に記載される公知の製造法により製造することができる。 In the present invention, 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea has the formula (I)

A compound having a general name of imazosulfuron (CAS RN 122548-33-8) (hereinafter referred to as Compound 1), and a known production method described in JP-A No. 64-38091 A commercially available preparation containing Compound 1 can also be obtained. The compound represented by the formula (II) (hereinafter referred to as compound 2) can be produced by a known production method described in JP-A-2004-123690.

  The composition of the present invention has herbicidal activity against a wide range of weeds, and can effectively control a wide range of weeds in paddy fields or upland where normal tillage cultivation and non-tillage cultivation are performed. Cause no phytotoxicity.

Examples of the field in the present invention include crop fields and vegetable fields.
Examples of the crop field in the present invention include food crop fields such as peanut fields, soybean fields, corn fields, and wheat fields, feed crop fields such as sorghum fields and oat fields, industrial crop fields such as cotton fields, and sugar families such as sugar cane fields. Crop fields can be mentioned. As a vegetable field in the present invention, a field for cultivating solanaceous vegetables (eggplant, tomato, pepper, pepper, potato, etc.), a field for cultivating cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae Fields where vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.) are grown, fields where asteraceae vegetables (burdock, garlic, artichokes, lettuce, etc.) are cultivated, lilies , Fields that cultivate onions, garlic, asparagus), fields that cultivate celery vegetables (carrots, parsley, celery, etc.), fields that cultivate vegetables such as spinach, spinach, chard, etc. Fields for cultivating perilla, mint, basil, lavender), strawberry field, sweet potato field Yam field, mention may be made of the taro fields and the like.

  The composition of the invention, barnyardgrass (Echinochloa oryzicola), barnyardgrass (Echinochloa crus-galli), Scirpus (Scirpus juncoides), Himekan Galei (Scirpus mucronatus), Koukiyagara (Scirpus planiculmis), pulp (Scirpus nipponicus), smallflower umbrellaplant (Cyperus difformis) , Cyperus serotinus, Krogwai (Eleocharis kuroguwai), Japanese oak (Monochoria vaginalis), Urikawa (Sagittaria pygmaea), Omodaka (Sagittari) pocumbens), Amerikaazena (Lindernia dubia), Taketoazena (Lindernia dubia), Azetougarashi (Lindernia angustifolia), Ooabunome (Gratiola japonica), Rotala indica (Rotala indica), Elatine triandra Schk (Elatine triandra), alisma canaliculatum (Alisma canaliculatum), e buckwheat Hime Misohagi (Ammannia coccinea), Taukogi (Bidens tripartita), American Sendangsa (Bidens frontosa), Kusanem (Aeschynomene indica), American Tsunosanane (Sesbania exaltata), Seri (Oenanthe) avanica, Potamogeton distinctus, Galium spurium, Sinapi arvensis, Brassica juncea, Hakobe (Stellaria mesi) ), Polygonum, Ibibi (Abutilon theophrasti), Ona fir (Xanthium strumaria), Ragweed (Ambrosia artemisifolia), Taraxumum officinaro (C) s), annual perennial weeds and perennial weeds occurring in paddy fields and / or upland fields such as Cyperus esculentus can be effectively controlled, and high safety (low phytotoxicity to paddy rice and wheat) ).

  The composition of the present invention can be used in the form of general agricultural chemicals, that is, the above active ingredients are dissolved or dispersed in a suitable liquid carrier, or mixed or adsorbed with a suitable solid carrier, for example, emulsion, oil agent, It may be formulated into a preparation such as a spray, wettable powder, powder, DL (driftless) powder, granule, fine granule, fine granule F, flowable, dry flowable, jumbo granule, tablet or the like. These preparations may further contain an emulsifier, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a mucilage agent, a stabilizer and the like, if necessary, and can be prepared by a method known per se.

  Examples of the liquid carrier (solvent) that can be used in formulating the composition of the present invention include water, alcohols (eg, methanol, ethanol, 1-propanol, 2-propanol, etherene glycol, etc.), and ketones. (Eg, acetone, methyl ethyl ketone, etc.), ethers (eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (eg, kerosene, fuel oil, machine oil, etc.) ), Aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (eg, dimethylformamide) , Dimethylacetoa Etc.), esters (eg, ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles (eg, acetonitrile, propionitrile, etc.) and the like. May be mixed and used at an appropriate ratio. Solid carriers (dilution / extension agents) include vegetable powders (eg, soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (eg, kaolin, bentonite, acid clay, clays such as clay, talc Talc such as powder, wax stone powder, silica such as diatomaceous earth, mica powder, etc.), alumina, sulfur powder, activated carbon, and the like. These may be used alone or in combination of two or more in an appropriate ratio. Also good. The liquid carrier or solid carrier is usually used in an amount of about 1 to 99% by weight, preferably about 1 to 80% by weight, based on the whole preparation.

  Surfactants that can be used as emulsifiers, spreaders, penetrants, dispersants, etc. when formulating the composition of the present invention include, for example, soaps, polyoxyethylene alkylaryl ethers (eg, Neugen, E. A 142; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), polyoxyethylene aryl esters (eg, Nonal; manufactured by Toho Chemical Co., Ltd.), alkyl sulfates (eg, Yumar 10, Yumar 40; manufactured by Kao Corporation) , Alkylbenzene sulfonates (eg, Neogen, Neogen T; manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neopelex; manufactured by Kao Corp.), polyethylene glycol ethers (eg, Nonipol 85, Nonipol 100, Nonipol 160; Sanyo Kasei) Non-ionic and anionic polymers such as polyhydric alcohol esters (eg, Tween 20, Tween 80; manufactured by Kao Corporation). Emissions-based surfactant is used. The surfactant can be used usually in an amount of about 0.1 to about 50% by weight, preferably about 0.1 to 25% by weight, based on the whole preparation.

In the composition of the present invention, the total amount of Compound 1 and Compound 2 is usually about 0.01 to 90% by weight. For emulsions, wettable powders, sprays, dry flowables, flowables, etc., a ratio of about 1 to 90% by weight, for oils, powders, DL (driftless) type powders, etc., a ratio of about 0.01-10% by weight, In the case of a fine granule, fine granule F, jumbo agent, granule, tablet or the like, it may be contained in a proportion of about 0.05 to 10% by weight.
Emulsions, wettable powders, and the like are sprayed after being appropriately diluted and increased (for example, 100 to 100,000 times) with water or the like.

  When the composition of the present invention is used in paddy fields, it is usually applied after direct sowing of paddy rice, after direct sowing of dry rice, and at or after transplanting of paddy rice. Further, when the composition of the present invention is used in a field, particularly when used in a wheat field, it is usually used in a pre-germination soil treatment or a foliage / soil treatment. The composition of the present invention can be safely used without any chemical damage even after 2 to 3 weeks after treatment.

The amount used in the case of using the herbicidal composition of the present invention varies depending on the application scene, application time, application method, target weed, cultivated crop, etc., but generally the amount of active ingredient (total amount of Compound 1 and Compound 2) is: In the case of paddy field, it is usually about 30 to 400 g, preferably about 50 to 200 g per hectare, and in the case of upland, it is about 30 to 2000 g, preferably about 50 to 1000 g per hectare.
In the composition of the present invention, the mixing ratio of Compound 1 and Compound 2 used as active ingredients is usually 1: 0.01 to 100, preferably 1: 0.1 to 10, and more preferably 1: by weight. It is in the range of 0.5-2.

The composition of the present invention can be prepared by formulating each active ingredient by the above-described formulation technique and then mixing them.
The composition of the present invention can be used by mixing with other herbicides as necessary. Further, it can be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, safeners, soil improvers and the like.

  The method for controlling weeds in paddy fields or upland fields in the present invention can be carried out by applying a preparation containing Compound 1 and Compound 2 as described above, and further a preparation containing Compound 1 and a compound. You may carry out by processing together with the formulation containing 2.

  Hereinafter, the present invention will be described in more detail with reference to Examples such as formulation examples and test examples, but the present invention is not limited thereto. The “parts” described in the examples all mean parts by weight.

Formulation Example 1
In a small kneader, 1.0 part of Compound 1, 1.0 part of Compound 2, Neocor YSK (dialkylsulfosuccinic acid ester surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 0.5 part, Toxanone GR31A (polycarboxylic acid type anionic surfactant: Sanyo Chemical Industries Co., Ltd.) 2.0 parts, Kunigel V1 (Bentonite: made by Kuminin Industry) 30.0 parts and calcium carbonate 65.5 parts, mixed and kneaded, extrusion granulator (RG-5M, Kikusui Seisakusho) Granules), dried with a fluidized bed dryer (MDB-400, manufactured by Fuji Powder), and then sieved with 16 to 48 mesh to produce granules.

Formulation Example 2
Compound 1 1.9 parts, Compound 2 1.9 parts, Ethylene glycol 9.0 parts, Antifoam E-20 (manufactured by Kao Corporation) 0.3 part, Sorbic acid 0.1 part, Isoelite L (manufactured by Shisui Port Sugar Co., Ltd.) 10.0 parts, After mixing 3.0 parts of New Calgen D-1518 (manufactured by Kao Corporation) and 2.0 parts of Agrisol FL-2017 (manufactured by Kao Corporation) with 71.8 parts of water and dispersing with a homomixer, the mixture was mixed with dynomill (Shin A flowable agent is produced by wet pulverization (one pass) using 1.0 mm glass beads, a filling rate of 85%, and a peripheral speed of 10 m / s.

Formulation Example 3
Compound 1 2.4 parts, Compound 2 2.4 parts, Microsphere F-80E (plastic hollow body: manufactured by Matsumoto Yushi Seiyaku Co., Ltd.) 2.4 parts, Olphine E1010 (manufactured by Nissin Chemical Industry Co., Ltd.) 3.0 parts, Toxanone GR-31A (Sanyo Chemical Industry Co., Ltd.) 2.0 parts, sodium tripolyphosphate 5.0 parts, Serogen 7A (Daiichi Kogyo Seiyaku Co., Ltd.) 3.0 parts, Kunigel V1 (Bentonite: made by Kuminin Industry) 10.0 parts and calcium carbonate 69.8 parts , Mixed with a predetermined amount of water, kneaded, granulated by an extrusion granulator equipped with a 1.5 mm screen (RG-5M, manufactured by Kikusui Seisakusho), and fluidized bed dryer (MDB-400, Granules are produced by drying with two powders.

Test Example 1: Herbicidal effect on Tainubier (greenhouse pot test)
Paddy soil was packed in a 50 cm ² foamed polystyrene pot, seeded with Tainubie seeds, and when Tainubier reached the 2.5 to 3.0 leaf stage, the flooding was made 5 cm.
Each of Compound 1 and Compound 2 is dissolved in acetone containing 2% (W / V) of Tween 20 (surfactant) and diluted with water so that the acetone concentration in the diluted solution becomes 10%. A dilution was prepared. Each of the drug dilutions was applied to the pots on which the above-mentioned Tainubies had grown so as to have the amounts described in Table 1.
Three weeks after the drug treatment, the effect on Tainubier (no action was set to 0 and complete death was set to 100) was observed and evaluated. The results are shown in Table 1.

Test Example 2: Herbicidal effect on the oak (greenhouse pot test)
Paddy soil was packed in a 50 cm ² foamed polystyrene pot, seeded with konagi seeds, and when the konagi reached the 2.5 to 3.0 leaf stage, the brine was set to 5 cm.
Compound 1 and Compound 2 are dissolved in acetone containing 2% (W / V) Tween 20 (surfactant) and diluted with water so that the acetone concentration in the diluted solution is 10% to prepare a drug diluted solution did. The drug dilution solution was applied to the pot where the above-mentioned poppies were grown so as to obtain the amount described in Table 2.
Three weeks after the drug treatment, the effect on the snapper was observed and evaluated (no action was 0 and complete death was 100). The results are shown in Table 2.

Test Example 3: Herbicidal effect on yamgra (pot test in greenhouse)
Steam-sterilized soil was packed in a 590 cm ² × 8 cm plastic pot, seeds of Yamgra were sown, and 1 cm of soil was covered.
Imazosulfuron suspension (suspension containing 40% of compound 1, trade name: Shibatite 40, manufactured by Sumika Takeda Agricultural Chemical Co., Ltd.) was diluted in water to prepare a drug diluent containing compound 1. Compound 2 is dissolved in acetone containing 2% (W / V) of Tween 20 (surfactant) and diluted with water so that the acetone concentration in the diluted solution becomes 10%. Was prepared. Furthermore, imazosulfuron suspension (suspension containing 40% of Compound 1, trade name: Shibatite 40, manufactured by Sumika Takeda Agrochemicals) and 2% of Tween 20 (surfactant) of Compound 2 (W / V) A solution of acetone was diluted at a predetermined ratio to prepare a drug diluent containing Compound 1 and Compound 2. Each of the drug dilutions was sprayed at an amount of 500 L of water per ha from the top of the pot seeded with the above-mentioned Yamgra seeds so as to have the amount shown in Table 3.
Three weeks after the drug treatment, the effect on Yaemgura (no action was set to 0 and complete death was set to 100) was observed and evaluated. The results are shown in Table 3.

Test Example 4: Herbicidal effect against peppers (greenhouse pot test)
Steam-sterilized soil was packed in a 590 cm ² × 8 cm plastic pot, seeds of Noharagarashi were sown, and 1 cm of soil was covered.
Imazosulfuron suspension (suspension containing 40% of compound 1, trade name: Shibatite 40, manufactured by Sumika Takeda Agricultural Chemical Co., Ltd.) was diluted in water to prepare a drug diluent containing compound 1. A 2% (W / V) acetone solution of compound 2 in Tween 20 (surfactant) is diluted with water so that the acetone concentration in the diluent is 10%, and a drug diluent containing compound 2 is diluted. Prepared. Furthermore, imazosulfuron suspension (suspension containing 40% of Compound 1, trade name: Shibatite 40, manufactured by Sumika Takeda Agrochemicals) and 2% of Tween 20 (surfactant) of Compound 2 (W / V) A solution of acetone was diluted at a predetermined ratio to prepare a drug diluent containing Compound 1 and Compound 2. Each of the drug dilutions was sprayed at an amount of 500 L of water per ha from the top of the pot seeded with the above seeds of Noharagara so that the amounts shown in Table 4 were obtained.
Three weeks after the drug treatment, the effect on Noragarashi (no action was set to 0 and complete death was set to 100) was observed and evaluated. The results are shown in Table 4.

Test Example 5: Damage to wheat (greenhouse pot test)
Steam-sterilized soil was packed in a 590 cm ² × 8 cm plastic pot, seeded with wheat seeds, and covered with 1 cm.
Imazosulfuron suspension (suspension containing 40% of Compound 1, trade name: Shibatite 40, manufactured by Sumika Takeda Agrochemicals) and Tween 20 (surfactant) of Compound 2 containing 2% (W / V) of acetone The solution was diluted at a predetermined ratio to prepare a drug diluent containing Compound 1 and Compound 2. The drug diluted solution was sprayed with an amount of water of 500 L per ha from the top of the pot seeded with the above wheat seeds so that the amount described in Table 5 was obtained.
Three weeks after the drug treatment, the effect on wheat (no action was set to 0 and complete death was set to 100) was observed and evaluated. The results are shown in Table 5.

試験例より明らかなように、本発明組成物は雑草（ヤエムグラ、ノハラガラシ等）に対する除草効果が高い。一方、作物（コムギ）に対する薬害は問題にならなかった。

As is clear from the test examples, the composition of the present invention has a high herbicidal effect on weeds (Yamegura, Noharagara, etc.). On the other hand, phytotoxicity to crops (wheat) was not a problem.

  According to the present invention, it can be applied at a low dose in paddy fields or upland fields, and a wide range of weeds can be controlled.

Claims (7)

[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

A herbicidal composition comprising a compound represented by the formula: A herbicidal composition for controlling weeds in paddy fields or upland fields, as an active ingredient
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

A herbicidal composition, wherein the weight ratio of [a] to [b] is in the range of 1: 0.1 to 1:10. The herbicidal composition according to claim 2, wherein the weight ratio of [a] to [b] is in the range of 1: 0.5 to 1: 2. It is a method to control weeds in paddy fields or upland fields, and at the same time or in combination
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

A method comprising applying the compound represented by the formula to soil or weed where weed grows or grows. It is a method to control weeds in paddy fields or upland fields, and at the same time or in combination
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

Applying the compound represented by the above to the soil or weed where the weed grows or grows in a weight ratio of [a] to [b] of 1: 0.1 to 1:10. A method characterized by. 6. The method according to claim 5, wherein the weight ratio of [a] to [b] is in the range of 1: 0.5 to 1: 2. As an active ingredient of a herbicidal composition for controlling weeds in paddy fields or upland fields,
[a] 1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;
[b] Formula (II)

Use in combination with a compound represented by