JP3230528B2 - Aqueous suspension pesticide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aqueous suspension pesticide composition. In particular, the present invention contains a herbicide as an active ingredient, and it is easy to spray and prepare a spray liquid as an undiluted solution,
It relates to an aqueous suspension composition having a low viscosity and being easily dispersible in water.

[0002]

2. Description of the Related Art Conventionally, granules and fine granules (granules) have been mainly used as herbicide dosage forms. These preparations are prepared by mixing the active ingredient with a carrier such as clay, bentonite, and talc. In order to uniformly apply such preparations, 2 / 10a is required.
~ 6Kg is required. The large weight and volume not only increases the load on the operator, but also has many disadvantages in terms of transportation and storage. There is also a wettable powder as another dosage form, which is mainly used for upland fields. However, since powdering during the preparation of the spray liquid is unavoidable, it tends to be avoided in recent years. In order to solve these difficulties, an aqueous suspension composition has been proposed (see JP-A-60-214701, JP-A-63-107901, and JP-A-1-110605). On the other hand, the applicant of the present invention has reported that a compound represented by the following general formula (I) and a salt thereof have substantially no phytotoxicity to crops and turf such as rice, wheat, barley, corn and soybean, It has been found that weeds in paddy fields and fields have excellent herbicidal activity at low doses (see JP-A-64-38091), but development of more advantageous formulations of these compounds is desired. Was. Therefore, as a result of various studies, the present inventors have found the present invention.

[0003]

According to the present invention, the compound represented by the general formula (I)

Embedded image [Wherein, Q represents a condensed heterocyclic group having an N-atom at the bridgehead which may have a substituent, W represents 0 or S, and R ₁ and R ₂
Represents an alkyl group, an alkoxy group or a halogen atom, and Z represents CH or N. And polyoxyethylene phenyl phenol ether sulfate, polyoxyethylene alkyl ether, polyoxyethylene allyl phenyl ether formaldehyde condensate, polyoxyethylene alkyl phenyl ether, polyoxyethylene phenyl alkyl allyl ether sulfate 1 selected from a salt, a polyoxyethylene alkyl allyl ether sulfate and a sucrose fatty acid ester
The present invention provides an aqueous pesticide composition containing a surfactant comprising a species or a mixture of two or more species. In the above general formula (I), Q represents a condensed heterocyclic group having an N atom at the bridgehead which may have a substituent, wherein the fused heterocyclic group having an N atom at the bridgehead is a bridge-like bond. Means a fused heterocyclic group in which both or one of the atoms at the head and the terminal, ie, the bridgehead atom, is a nitrogen atom. The fused heterocyclic group having an N atom at the bridgehead which may have a substituent represented by Q is, for example, a compound represented by the general formula

[0004]

Embedded image Wherein ring a and ring b each represent a nitrogen-containing heterocyclic ring which may be substituted, and one hydrogen atom bonded to a constituent carbon atom other than the bridgehead is removed from the condensed heterocyclic ring represented by the formula Represents a group. Preferred specific examples of the fused heterocyclic ring include:

[0005]

Embedded image Is included. Particularly preferred are imidazo 1,2-a
Pyridine, imidazo 2,1-b thiazole and imidazo [1,2-b pyridazine. The fused heterocyclic group having an N atom at the bridgehead is, for example, a substituent such as a hydroxy group, an amino group, a cyano group, a sulfamoyl group, a sulfamoyloxy group, a mercapto group, a nitro group, a halogen atom, an organic residue or a sulfo group. May be substituted the same or different from one to three. Preferred substituents among the above are a cyano group, a sulfamoyl group, a sulfamoyloxy group, a nitro group, a halogen atom or an organic residue. Particularly preferred substituents are cyano groups, halogen atoms or organic residues. Here, the halogen atom means, for example, fluorine, chlorine, bromine, iodine and the like. The organic residue is, for example, a hydrocarbon group, a heterocyclic group, an acyl group,

[0006]

Embedded image Wherein Q ₁ and Q ₂ have the same meanings as defined above, a carbamoyl group, a carbamoyloxy group, a ureido group, a thiocarbamoyl group, a carboxyl group or a group represented by the formula —O
—SO ₂ —Q ₂ [wherein Q ₂ has the same meaning as described above]. The alkyl group represented by R1 and R2 preferably represents a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl,
n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-
Pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, cyclohexyl and the like are used, and the alkoxy group preferably means a linear or branched alkoxy group having 1 to 6 carbon atoms, for example, methoxy, ethoxy, n -Propoxy, isopropoxy,
n-butoxy, isobutoxy, sec-butoxy, tert-
Butoxy, n-pentyloxy, n-hexyloxy and the like are used, and halogen, fluorine, chlorine, bromine and iodine are used. R ₁ and R ₂ are more preferably each a lower alkyl group (eg, an alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl) or a lower alkoxy group ( For example, carbon number 1 such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, etc.
To 4 alkoxy groups) or a halogen atom (such as fluorine, chlorine, and bromine). Most preferably, R ₁ and R ₂ are each a methyl group, a methoxy group or chlorine. W is preferably O. Preferably Z is CH. Compound (I) has an acidic group in the molecule.

[0007]

Embedded image And an inorganic base salt or an organic base salt with an acidic group such as a sulfo group and a carboxyl group in the substituted component,
Further, an inorganic acid addition salt or an organic acid addition salt can be formed with a basic nitrogen atom in the molecule and a basic group such as an amino group in the substitution component. As the inorganic base salt of the compound (I), for example, an alkali metal (sodium, potassium, etc.)
Salts with alkaline earth metals (such as calcium) and ammonia, and organic base salts of compound (I) include, for example, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylbenzylamine, pendylamine, ethanol Salts with amines, diethanolamine and the like are used. Examples of the inorganic acid addition salts of compound (I) include hydrochloric acid, hydrobromic acid, sulfuric acid,
Salts with nitric acid, phosphoric acid and the like, and as organic acid addition salts of compound (I), for example, salts with p-toluenesulfonic acid, methanesulfonic acid, formic acid, trifluoroacetic acid and the like are used. Particularly preferred compounds belonging to compound (I) or a salt thereof, which is an active ingredient of the present invention, include:

[0008]

Embedded image

On the other hand, a surfactant is used in the composition of the present invention. As the surfactant, it has been found that an anionic surfactant and a nonionic surfactant are desirable. Examples of the anionic surfactant include sulfonic acid-based, for example, alkyl naphthalene sulfonate, lignin sulfonate, alkylbenzene sulfonate, naphthalene sulfonate formalin condensate, dialkyl sulfosuccinate ester salt, and sulfate-based, for example, poly Preferred are oxyethylene phenyl alkyl allyl ether sulfate, polyoxyethylene alkyl allyl ether sulfate, polyoxyethylene phenyl phenol ether sulfate, and the like.

Examples of the nonionic surfactant include ether-type surfactants such as polyoxyethylene alkyl ether, polyoxyethylene allyl phenyl ether formaldehyde condensate, polyoxyethylene alkyl phenyl ether, polyoxyethylene distyrenated phenyl ether, and polyoxyethylene Preferred are polyoxypropylene block polymers, sucrose fatty acid esters and the like. Further, the nonionic surfactant used in the present invention is HL
Those in which B is 10 to 18 are preferred. More preferably, it is in the range of 12-18.

These surfactants may be used alone or in combination of two or more. In the case of a mixed system, it is particularly preferable to use an anionic surfactant and a nonionic surfactant in combination. The compounding ratio is usually used in a nonionic surfactant: anionic surfactant = 30 to 80:70 to 20 (weight ratio). Preferably 40-70: 60-30,
More preferably, the ratio is 50-60: 50-40.

Among them, polyoxyethylene phenyl phenol ether sulfate [eg, Agrisol FL-2017 (trade name of Kao Corporation), HLB15] and polyoxyethylene alkyl ether [eg, New Calgen D-1518 (Takemoto) YLB Co., Ltd., HLB15], polyoxyethylene allyl phenyl ether formaldehyde condensate [for example, Newcalgen E-300 (Takemoto Yushi)
HLB15], polyoxyethylene alkyl phenyl ether [for example, Newcalgen D-41]
0 (trade name of Takemoto Yushi Co., Ltd.), HLB13, Nonipol 9
5 (trade name of Sanyo Chemical Co., Ltd.), HLB13, Neugen EA
130T (trade name of Daiichi Kogyo Seiyaku Co., Ltd.), HLB13], sucrose fatty acid ester [for example, sucrose laurate ester, H
LB16], a mixture of polyoxyethylene phenylalkyl allyl ether sulfate and a mixture of polyoxyethylene alkyl allyl ether sulfate [for example, Solpol 3078 (trade name of Toho Chemical Co., Ltd.)] (mixing ratio) 1: 1-1: 3) is preferred. The addition amount of these surfactants is 1 to 15% (w / w) in the composition, preferably 3 to
10% (w / w). When surfactants are used as a mixture, the total amount may be within the above range.

The composition of the present invention is obtained by combining a compound of the general formula (I) with a specific surfactant as described above.
Consists of a water-stable dispersion. A third component may be added to such a composition according to the following various purposes.

For the purpose of stabilizing the suspension state and adjusting the viscosity, a water-soluble polymer, a protective colloid agent and a suspension aid are used. Examples thereof include sodium polyacrylate, carboxymethylcellulose, polyvinyl alcohol, agrizole FL-104FA (Kao Corporation, a polyol-based special polymer), gum arabic, gelatin, xanthan gum, Aerosil (Nippon Aerosil). No. These may be used alone or as a mixture of two or more, and the amount of addition is 0.1 to 15% (w / w) in the composition.

To prevent freezing, ethylene glycol,
A hydrophilic solvent such as diethylene glycol, glycerin, and methanol may be added in the composition in an amount of 5 to 15% (w / w). For adjusting the specific gravity, a hydrophobic solvent such as kerosene or liquid paraffin can be added in an amount of 2 to 20% (w / w) in the composition. When foaming occurs during the manufacturing operation, a silicone-based antifoaming agent (for example, Antihome E-20 (Kao Corporation) or the like) is added at 0.05 to 0.5% (w / w) of the composition, Preservatives such as sorbic acid, dehydroacetic acid, propionic acid or salts thereof, and parahydroxybenzoic acid ester may be added in an amount of 0.1 to 2% (w / w) in the composition. In order to spread it, one to three other herbicides may be mixed, which can be expected to be effective against a wide range of weeds. The following is a list of herbicides and their mixing ratios: [] indicates a mixed part per 1 part by weight of compound A. 0-3-tert-
Butylphenyl N- (6-methoxy-2-pyridyl) -N
-Methyl carbamate (pyributicarb) [3 to 15], 1
-(Α, α-dimethylbenzyl) -3- (4-methylphenyl) urea (Dimron) [8-30], 3,7-dichloro-
8-quinolinecarboxylic acid (quinclorac) [2 to 7],
2,6-diethyl-N- (propoxyethyl) -chloroacetanilide (pretilachlor) 2-7], S, S-dimethyl 2- (difluoromethyl) -4- (2-methylpropyl) -6- (trifluoromethyl ) -3,5-pyridinedicarbothioate (dithiopyr) 0.5-2.0], 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide (HW-5
2) [5-20], S-benzyl = 1,2-dimethylpropyl (methyl) thiocarbamate (esprocarb) 5-2
Five].

The composition of the present invention can be prepared according to a preparation method known per se. For example, all components to be used are sufficiently stirred and mixed by a high-speed stirrer (about 20 to 60 minutes)
After that, a method of finely pulverizing and dispersing with a wet pulverizer such as a sand grinder (Production method 1), or a raw powder of a herbicide of an active ingredient is pulverized with a dry pulverizer such as a jet miser, and other ingredients are pulverized. Mix with high-speed stirrer (about 30 ~
(For 90 minutes) and dispersing (manufacturing method 2).
As understood from the above-mentioned production method, the active ingredient of the present invention is required to be dispersed in water in the form of fine particles in the composition. The same applies when other powder components are used. The average particle size of the fine particles is about 10 μ or less, preferably 5 μ or less.

Compound (I) of the active ingredient used in the present invention
Or a salt thereof is a very low dose and a wide range of weeds, such as, for example, foxtail, tamayatsuri, dogfly, konagi, urikawa, pine tree, mizukayatsuri, kuroguwai,
Paddy field weeds such as Heramodaka, Omodaka, Taiwan-Yamamai, Azena, Kikashigusa, Hirumshiro, Chowadad, Mizohakobe, Meechishiba, Enokorogusa, Aoubiyu, Ichibi, Akaza, Inutade, Suberihyu, Pseudomonas terrestris, A. Not only has excellent herbicidal activity against field weeds such as oak millet, seiban sorghum, mussels, oats, blackgrass, umanochiyaki, kohakobe, mustards, shrimp grass, chamomile, and twigs, but also rice, wheat, barley, corn, There is almost no phytotoxicity to crops such as soybeans, indicating high safety. Therefore, the composition containing the compound (I) or a salt thereof according to the present invention exhibits an excellent selective herbicidal effect between crops and various weeds, has low toxicity to mammals and seafood, and is environmentally friendly. Without contamination, it can be used very safely as a herbicide for paddy fields, fields, orchards or non-agricultural lands. The amount of the composition of the present invention varies depending on the application scene, application time, application method, target grass species, cultivated crops, and the like, but is generally an active ingredient (compound (I) or a salt thereof).
About 0.05 to 50 g per 1 paddy field, preferably
It is about 0.1 to 5 g, and about 0.05 to 20 g, preferably about 0.1 to 5 g per are of field.

[0018]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below with reference to embodiments. Example 1 1.8 g of compound A, 3 g of Newcalgen D-1518, 2 g of agrizole FL2017, and agrizole FL104FA10
g, Aerosil COK84 2g, Isoelite L 10g,
Anti-Home E-20 0.2g, Ethylene glycol 10
g, 0.1 g of sorbic acid and 60.9 g of water were weighed, and all components were mixed by a homogenizer for 30 minutes, and then wet-milled with Dynomill KDL to prepare 100 g of a uniform suspension. Examples 2 to 6 Each raw material shown in Table 1 was weighed, and a suspension was prepared in the same manner as in Example 1 below.

[0019]

[Table 1] Table 1 Note 1.) Raw material name Newcalgen D-1515: trade name, manufactured by Takemoto Yushi Co., Ltd. Newcalgen E-300: 〃, １０ Newcargen D-410: 〃, sucrose lauric ester Generic name, manufactured by Takemoto Yushi Co., Ltd. Solpol 3078 Trade name Toho Chemical Industry Co., Ltd. Agrisol FL2017 〃 Kao Corporation Aerosil COK84 〃 Nippon Aerosil Co., Ltd. Isoelite L 〃 Saltwater Port Refining Co., Ltd. Antihome E-20 〃 Kao Corporation 2. Dispersion Properties Dispersion when dropped into water is excellent …… ◎ Good …… ○ Poor …… △ Not dispersed …… ×. Viscosity was measured with a B-type viscometer.

[0020]

[Table 2] The composition thus obtained is applied to a paddy field under flooding per 10a.
Spray 300-1000 g as undiluted solution, and when using it in the field, dilute 200-800 times with water and spray.
Excellent effect on a wide range of weeds.

Test Example A suspension having the composition shown in Table 2 was prepared in the same manner as in Example 1. Dispersibility of these suspensions (Test Examples 1 to 4) and adhesion to plants were observed, and the results are shown in Table 2. For the dispersibility, each suspension was prepared, left at room temperature for 48 hours, and then visually observed for its dispersibility. Attachment to the plant body was performed by keeping the third leaf of the rice at the 5 leaf stage horizontal, dropping 0.2 ml of a suspending agent in each case, observing the degree of wetting with the naked eye, and performing relative comparison.

[0022]

The compound of the general formula (I) used as an active ingredient in the present invention has no phytotoxicity to rice and shows a remarkable herbicidal effect at a low dose on weeds. On the other hand, the composition of the present invention is stable, has low viscosity and good dispersibility in water, and can be directly applied to a flooded sewage paddy field with a small amount of application, and can exhibit a selective herbicidal effect. When a nonionic surfactant having a specific HLB value and an anionic surfactant are used in combination, a stable pesticide suspension having more excellent dispersibility can be obtained. In addition, such a preparation does not adhere to plants after spraying, and can exhibit an effective herbicidal action.

Continuation of the front page (58) Field surveyed (Int.Cl. ⁷ , DB name) A01N 47/36 101 A01N 25/04 102 A01N 25/30 CA (STN)

Claims (6)

(57) [Claims] 1. A compound of the general formula (I) [Wherein, Q represents a condensed heterocyclic group having an N-atom at the bridgehead which may have a substituent, W represents 0 or S, and R ₁ and R ₂
Represents an alkyl group, an alkoxy group or a halogen atom, and Z represents CH or N. And polyoxyethylene phenyl phenol ether sulfate, polyoxyethylene alkyl ether, polyoxyethylene allyl phenyl ether formaldehyde condensate, polyoxyethylene alkyl phenyl ether, polyoxyethylene phenyl alkyl allyl ether sulfate 1 selected from a salt, a polyoxyethylene alkyl allyl ether sulfate and a sucrose fatty acid ester
An aqueous pesticidal composition in the form of a suspension, comprising a surfactant comprising a species or a mixture of two or more species. 2. The composition according to claim 1, wherein a nonionic surfactant having an HLB of 10 to 18 and an anionic surfactant are used. 3. A compound of the general formula (I): 3. The composition according to claim 1, wherein X is CH or N, and Y is a hydrogen atom or a lower alkoxy group. 4. The compound of the general formula (I) is N- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl)-
The composition according to claim 3, which is N '-(4,6-dimethoxy-2-pyrimidinyl) urea. 5. A compound of the formula (I) in an amount of 0.5 to 25% (w /
5. The composition according to any one of claims 1 to 4, comprising w) and 1 to 15% (w / w) of the surfactant. 6. N- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -N '-(4,6-dimethoxy-2-pyrimidinyl) urea 0.8 to 15% (w / w) ) And Newcargen D-1518, Newcargen E-300, Newcargen D-410, Solpol 3078 and Acrysol FL201
7 and 3 to 10% (w / w) of a mixture of one or two selected from sucrose laurate.
A composition as described.