JPH1121203A - Herbicidal composition and its use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition that manifests effective combating activity against weeds that are important in the cultivation of rice plant by using 3-substituted phenyl pyrazole derivative, (RS)-bromo-N-(α,α- dimethylbenzyl)-3,3-dimethylbutyl amide (compound a) and 2-[2-(3- chlorophenyl)-2,3-epoxypropyl]-2-ethylindiane-1,3-dione (compound b). SOLUTION: This herbicidal composition is obtained by using (A) a 3- substituted phenylpyrazole derivative of the formula [R is COOR<6> (R<6> is a 1-6C alkyl); R<1> is a 1-6C alkyl; R<2> is H; X1 and X<2> are each a halogen; Y is O; n is 0, 1], (B) the compound a and (C) the compound b in which the total of the components A, B and C is 3-50 pts.wt. per 100 pts.wt. of the composition and the weight ratio of the component A: the component B: the component C is preferably 1:(1-100):(5-20).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a compound of the general formula (I)

Embedded image [Where R is

Embedded image -Y ¹ R ³ (wherein, R ³ is (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₂ -C ₆₎ alkenyl, (C ₂ -C ₆ ) represents an alkynyl group, and Y ¹ represents an oxygen atom or a sulfur atom.),

Embedded image —Y ² CH (R ⁴ ) —CO—OR ⁵ (wherein, R ⁴ represents a hydrogen atom or a (C ₁ -C ₆ ) alkyl group, and R ⁵ is a (C ₁ -C ₆ ) alkyl Group, halo (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, and Y ² represents an oxygen atom, a sulfur atom or a nitrogen atom.) ,

[0002]

-COOCH (R ⁴ ) -CO-Y ¹ R ⁵ (wherein R ⁴ , R ⁵ and Y ¹ are as defined above), or

Embedded image -COOR ⁶ (wherein, R ⁶ is (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₂ -C ₆₎ alkenyl, (C ₂ -C ₆ ) represents an alkynyl group), and R ¹ represents a (C ₁ -C ₆ ) alkyl group;
R ² is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group or a halo (C ₁ -C ₆ )
X represents an alkyl group, X ¹ and X ² are the same or different and represent a halogen atom, and Y is O, S, SO, SO ₂ or NH
And n represents an integer of 0 or 1. 3-
Substituted phenylpyrazole derivatives and (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutylamide and 2- (2- (3-chlorophenyl)
-2,3-epoxypropyl) -2-ethylindane-
The present invention relates to a herbicide composition containing 1,3-dione and a method for using the same.

[0003]

2. Description of the Related Art A 3-substituted phenylpyrazole derivative represented by the general formula (I) is described in JP-A-3-163630 and JP-A-4-211065, and is described to be useful as a herbicide. (RS) -2-bromo-N-
(Α, α-dimethylbenzyl) -3,3-dimethylbutyramide (hereinafter referred to as compound A) is disclosed in JP-B-56-43.
No. 455, 2- (2- (3-chlorophenyl)-
2,3-epoxypropyl) -2-ethylindane-
1,3-dione (hereinafter referred to as compound B) is disclosed in
It is a compound having a known herbicidal activity described in Japanese Patent No. 304043.

[0004]

At present, as important weeds in paddy rice cultivation, for example, nobies (common name of rice millet, annual grasses of grass family), tamayatsuri (cyperaceae, annual grasses), pine flies (cyperaceae, perennial grasses), urikawa ( There is an important problem to control, such as Omodaca, perennial grass, and fireflies (Cyperaceae, perennial grass). Especially, Urikawa has few drugs that can be controlled accurately, and creation of new drugs is desired.

[0005]

In view of the above situation, the present inventors have conducted intensive studies to create a novel herbicide composition, particularly an agent capable of accurately controlling Urikawa in paddy rice cultivation. Is completed. The present invention uses a mixture of a 3-substituted phenylpyrazole derivative represented by the general formula (I) and a compound A or a compound B to produce important weeds such as Nobie, Tamagatsuri,
It has a synergistic effect that cannot be expected from the effect of single use of each of the drugs, such as pinewood, urikawa, firefly, etc., and especially synergistic effect on urikawa.

Table 1 shows typical examples of the 3-substituted phenylpyrazole derivative represented by the general formula (I) of the present invention, but the present invention is not limited to these compounds. General formula (I)

Embedded image

[0007]

[Table 1]

[0008]

[Table 2]

[0009]

[Table 3]

[0010]

[Table 4]

[0011]

[Table 5]

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The herbicidal composition of the present invention comprises a composition 1
It is sufficient to mix the 3-substituted phenylpyrazole derivative represented by the general formula (I), which is an active ingredient compound, with the compound A and the compound B in a proportion of 3 to 50 parts by weight with respect to 00 parts by weight. 1 to 100 parts by weight of compound A and 5 to 5 parts by weight of compound B are added to 1 part by weight of the 3-substituted phenylpyrazole derivative represented by the general formula (I) in the component compounds.
What is necessary is just to mix | blend in the ratio of the range of 20 weight part. When the herbicidal composition of the present invention is used, a suitable solid carrier and / or a liquid carrier and the like, and if necessary, an auxiliary agent and the like are blended in an appropriate ratio in accordance with a conventional method for agrochemical formulation, and dissolved and suspended. It may be mixed, impregnated, adsorbed or adhered, and prepared and used in an appropriate dosage form depending on the purpose of use, for example, an emulsion, powder, granule, wettable powder or flowable.

The solid carrier used in the present invention includes, for example, clays such as kaolin, bentonite and acid clay, talcs such as talc and pyrophyllite, diatomaceous earth, silica sand, mica, synthetic silicate, and silica such as synthetic highly dispersed silicic acid. Kind, pumice stone,
Inorganic mineral powder such as sand can be exemplified. Examples of the liquid carrier include methyl alcohol, ethyl alcohol, alcohols such as ethylene glycol, acetone,
Ketones such as methyl ethyl ketone and cyclohexanone,
Ethyl ether, dioxane, tetrahydrofuran,
Ethers such as cellosolve, kerosene, aliphatic hydrocarbons such as kerosene, benzene, toluene, xylene, solvent naphtha, aromatic hydrocarbons such as methylnaphthalene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, and chlorobenzene These solid carriers or liquid carriers may be used alone or in combination of two or more.

As the auxiliary agent usable in the present invention, for example, a surfactant, a fixing agent, a dispersant, a thickener, a binder and the like can be used. As the surfactant, for example, a polyoxyethylene alkylaryl Ether, polyoxyethylene sorbitan monolaurate, alkyl allyl sorbitan monolaurate, alkyl benzene sulfonate, alkyl naphthalene sulfonic acid, lignin sulfonate, higher alcohol sulfate ester salt and the like. Can be used alone or in combination of two or more. As a fixing agent, a dispersing agent, a thickening agent and a binder, for example, casein, gelatin, starch, carboxymethylcellulose, alginic acid, agar, polyvinyl alcohol, sodium polyacrylate, gum arabic, xanthan gum and the like may be used as necessary. Can be.

The herbicidal composition of the present invention can be used, for example, as important pests in paddy fields such as nobies (Echinochloacrus-galli), cyperus (Cyperus difformis), and pine trees (Eleochar).
is acicularis), Urikawa (Sagittaria pygmaea),
Hotarui (Scirpus juncoides Roxb.c.subsp. Hotarui
) Etc., and exhibit an excellent herbicidal effect on weeds, and particularly on Urikawa, a synergistic effect which cannot be conceived as compared with the case where each agent is used alone. When using the herbicidal composition of the present invention, the composition in the form of a preparation according to the purpose may be used as it is, or may be diluted with water or the like, and the amount used depends on the size of the paddy rice to be controlled. The amount of the active ingredient compound is usually 0.01 g per 10 ares or more.
The treatment may be performed within the range of 1 kg, preferably 0.1 kg.
g to 0.1 kg.

[0016]

Embodiment 1 Granules 10% powder of compound 19 (containing white carbon) 1.1 parts 90% powder of compound A (containing white carbon) 7.0 parts 90% powder of compound B (containing white carbon) 1.2 parts Powdered polyethylene ( 5.0 parts Potassium chloride 81.2 parts Surfynol 465 (Air Products) 3.0 parts Gohsenol GL-05 (Nippon Gohsei) 0.5 parts Sodium polyacrylate 1.0 Parts ────────────────────────────────── Total 100.0 parts

Embodiment 2 Granules 10% powder of compound 19 (containing white carbon) 1.1 parts 90% powder of compound A (containing white carbon) 7.0 parts 90% powder of compound B (containing white carbon) 1.2 parts Bentonite 30. 0 part Calcium carbonate 57.3 parts Soda ash 1.0 part Toxanone GR-31A (40% product, manufactured by Sanyo Chemical Industries) 2.5 parts Newcol 565SNC (Nippon Emulsifier) 1.0 part Neocol YSK (No. 0.5 parts 製 Total (as dry matter) ) 100.0 parts

Embodiment 3 Flowable formulation 10% powder of compound 19 (containing white carbon) 0.21 part 90% powder of compound A (containing white carbon) 12.60 parts 90% powder of compound B (containing white carbon) 2.10 parts Hytenol N -08 (Daiichi Kogyo Seiyaku Co., Ltd.) 0.30 parts Demol ST (Kao Corporation) 0.50 parts Propylene glycol 10.00 parts Silicon KM-73 0.50 parts Proxel GXL (Zeneca Corporation) 0.10 parts Rhodopol 23 (manufactured by Rope Poulin) 0.20 parts Kunipia G (manufactured by Kunimine Industries) 1.50 parts Water 71.99 parts ───────────────────── １０ Total 100.00 copies

Test Example 1 Weeding effect on paddy rice weeds before emergence The soil was packed into a 1/1000 aret pot to make a paddy field, and Urikawa tuber, a paddy weed, was adjusted to a state before emergence. This was treated with the herbicidal composition of the present invention as a spray solution having a predetermined concentration. Twenty-one days after the treatment, the herbicidal effect was investigated, and the herbicidal effect was calculated in comparison with the non-treatment.

The results are shown in Table 2.

[Table 6]

Test Example 2 Herbicidal effect on paddy rice weeds after germination
The tuber of Urikawa, a paddy field weed, was adjusted to the 1.5 leaf stage. This was treated with the herbicidal composition of the present invention as a spray solution having a predetermined concentration. Twenty-one days after the treatment, the herbicidal effect was investigated, and the herbicidal effect was calculated in comparison with the non-treatment. Third result
It is shown in the table.

[0022]

[Table 7]

Claims (5)

[Claims] 1. A compound of the general formula (I) [In the formula, R is the following formula: -Y ¹ R ³ (wherein, R ³ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) An alkenyl group, a (C ₂ -C ₆ ) alkynyl group, and Y ¹ represents an oxygen atom or a sulfur atom.), -Y ² CH (R ⁴ ) -CO-OR ⁵ (wherein R ⁴ represents a hydrogen atom or a (C ₁ -C ₆ ) alkyl group, R ⁵ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group , (C ₂ -C ₆ ) alkynyl group, and Y ² represents an oxygen atom, a sulfur atom or a nitrogen atom.), Embedded image wherein —COOCH (R ⁴ ) —CO—Y ¹ R ⁵ (wherein R ⁴ , R ⁵ and Y ¹ are the same as described above; or -COOR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group , (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group.), R ¹ represents a (C ₁ -C ₆ ) alkyl group,
R ² is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group or a halo (C ₁ -C ₆ )
X represents an alkyl group, X ¹ and X ² are the same or different and represent a halogen atom, and Y is O, S, SO, SO ₂ or NH
And n represents an integer of 0 or 1. 3-
Substituted phenylpyrazole derivatives and (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutylamide and 2- (2- (3-chlorophenyl)
-2,3-epoxypropyl) -2-ethylindane-
A herbicidal composition comprising 1,3-dione. 2. (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethyl based on 1 part by weight of a 3-substituted phenylpyrazole derivative represented by the general formula (I). 1 to 100 parts by weight of butylamide and 2- (2-
(3-chlorophenyl) -2,3-epoxypropyl)
2. The herbicidal composition according to claim 1, comprising -2-ethylindane-1,3-dione in a proportion of 5 to 20 parts by weight. 3. The herbicidal composition according to claim 1, wherein the herbicidal composition is for paddy rice. 4. A compound of the general formula (I) for controlling undesired weeds. [Wherein, R is the following formula: -Y ¹ R ³ (wherein, R ³ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) An alkenyl group, a (C ₂ -C ₆ ) alkynyl group, and Y ¹ represents an oxygen atom or a sulfur atom.), And Y ² CH (R ⁴ ) —CO—OR ⁵ (wherein R ⁴ represents a hydrogen atom or a (C ₁ -C ₆ ) alkyl group, R ⁵ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group , (C ₂ -C ₆ ) alkynyl group, and Y ² represents an oxygen atom, a sulfur atom or a nitrogen atom.), ## STR9 ## -COOCH (R ⁴ ) -CO-Y ¹ R ⁵ (wherein, R ⁴ , R ⁵ and Y ¹ are the same as described above; or -COOR ⁶ (wherein R ⁶ is a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group , (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group.), R ¹ represents a (C ₁ -C ₆ ) alkyl group,
R ² is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group or a halo (C ₁ -C ₆ )
X represents an alkyl group, X ¹ and X ² are the same or different and represent a halogen atom, and Y is O, S, SO, SO ₂ or NH
And n represents an integer of 0 or 1. 3-
Substituted phenylpyrazole derivatives and (RS) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutylamide and 2- (2- (3-chlorophenyl)
-2,3-epoxypropyl) -2-ethylindane-
A method for using a herbicidal composition, comprising treating an effective amount of a herbicidal composition containing 1,3-dione. 5. The use of the herbicidal composition according to claim 4, wherein the herbicidal composition is for paddy rice.