JP2001039804A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicidal composition which exhibits higher herbicidal effects, possesses broad weed control spectra, shows herbicidal characteristics excellent in the safety and is useful as a foliage or soil treatment by mixing plural herbicidal active ingredients. SOLUTION: This herbicidal composition is obtained by including (A) 2-[2-(3- chlorophenyl)-2,3-epoxypropyl]-2-ethylindan-1,3-dione or its optical isomer and (B) at least one kind of compounds which have a triazine skeleton, preferably 1,3,5-triazine skeleton and exhibit herbicidal activity as active ingredients. Further, it is favorable that the ingredient A is (-)-2-[2-(3-chlorophenyl)-2,3- epoxypropyl]-2-ethylindan-1,3-dione and the ingredient B is a compound of the structure represented by the formula [R1 to R3 are each -AR4 (A is S or 0; R4 is a 1-3 C alkyl or the like) or a halogen] particularly 2-chloro-4- ethylamino-6-isopropyl-amino-1,3,5-triazine or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a herbicide composition for efficiently controlling various harmful weeds by mixing two kinds of herbicide active ingredients.

[0002]

2. Description of the Related Art At present, many compounds having herbicidal activity are known, some of which are commercially available and put to practical use. However, they have high herbicidal effects, have a wide herbicidal spectrum, and are excellent in herbicides safe for crops. Herbicides having properties are desired. Existing herbicides do not always meet this requirement. Many compounds having a triazine skeleton and having herbicidal activity have been reported, and some of them have been put to practical use. For example, 1,3,5-triazine herbicides used for corn cultivation have a broad spectrum of herbicidal activity, but they are still insufficient and require a large amount of drug. In some cases, usage was restricted. On the other hand, 2-
[2- (3-Chlorophenyl) -2,3-epoxypropyl] -2-ethylindane-1,3-dione is a herbicide described in JP-A-2-304443, and its optically active form is It is a herbicide described in Japanese Patent Application No. 10-285042.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to develop a herbicide having a higher herbicidal effect, a broader herbicidal spectrum, and excellent herbicidal properties.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to find an excellent herbicide, and as a result, have found that 2- [2- (3
-Chlorophenyl) -2,3 epoxypropyl] -2-
When ethylindane-1,3-dione or an optically active compound thereof is used in combination with a herbicide having a triazine skeleton, various weeds can be effectively herbicidally treated by soil treatment or foliage treatment on weeds in agricultural or non-agricultural lands. And their herbicidal efficacy is synergistically increased compared to when they are used alone, can be used at lower doses, further broadens the herbicidal spectrum, and has a wide range, especially in corn fields. It has been found that weeds can be selectively controlled, leading to the present invention. That is, the present invention relates to (I) 2- [2-
(3-chlorophenyl) -2,3-epoxypropyl]
The present invention relates to a herbicidal composition comprising, as active ingredients, -2-ethylindane-1,3-dione or an optical isomer thereof, and (II) at least one compound having a triazine skeleton and having herbicidal activity.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The component (I) constituting the herbicidal composition of the present invention comprises (±)-
2- [2- (3-chlorophenyl) -2,3-epoxypropyl] -2-ethylindane-1,3-dione (racemate, generic name indanophane, hereinafter referred to as "indanophane") or an optically active compound thereof There is (-)
-2- [2- (3-chlorophenyl) -2,3 epoxypropyl] -2-ethylindane-1,3-dione (hereinafter referred to as "(-)-indanophane"). As described above, indanophane is a herbicide described in Japanese Patent Application Laid-Open No. 2-304043, which is mainly used for paddy fields. In addition, (-) indanophan is a herbicide described in Japanese Patent Application No. 10-285042, which is a herbicide that has superior herbicidal activity, particularly greater water solubility than indanophan, and is expected to be used in fields other than rice fields. Yes, it is particularly preferred as the active ingredient of (I). Examples of the compound having a triazine skeleton (II) constituting the composition of the present invention and having herbicidal activity include various known 1,3,5-triazine skeletons or 1,2,2-triazine skeletons.
Although a compound having a 4-triazine skeleton and having a herbicidal activity is exemplified, a compound having a 1,3,5-triazine skeleton is preferable, and particularly, a compound having the following general formula (1)

[0006]

Embedded image

[0007] {wherein, R ^1, R ² and R ³ are each independently, -AR ⁴ (A represents a sulfur atom or an oxygen atom, R ⁴
Represents an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms. ^{), - NR 5 R 6 (} R 5, R 6 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, 3 carbon
6 represents a cycloalkyl group. ) Or a halogen atom. Compounds represented by｝ are preferred.

In the general formula (1), when R ⁴ is an alkyl group, a methyl group, an ethyl group, an n-propyl group, an i-
Represents a propyl group, in the case of an alkenyl group, a vinyl group,
It represents an alkenyl group having 2 to 3 carbon atoms such as an allyl group, and these groups may be further substituted. When R ⁵ and R ⁶ are alkyl groups, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, s
-Represents a linear or branched alkyl group having 1 to 5 carbon atoms such as a butyl group and a pentyl group, and in the case of an alkenyl group, a carbon number having a linear or branched chain such as a vinyl group, an allyl group, and a methallyl group. It represents an alkenyl group of 2 to 5, and in the case of a cycloalkyl group, a cycloalkyl group having 3 to 6 carbon atoms such as a cyclopropyl group and a cyclohexyl group.
These groups may be further substituted by a cyano group, a halogen atom and the like.

[0009] Among the triazine compounds of the general formula (1)
Or R¹ , R^Two And R^Three Of which is -AR^Four Group or
A halogen atom, and the remaining two are -NR^Five R⁶ In the base
Compound. In this case, -AR^Four Is -SC
H_Three , -OCH_Three And the like, and as the halogen atom,
A chlorine atom or a fluorine atom is preferable.^Five , R⁶ Is one side
Is preferably a hydrogen atom and the other is an alkyl group.
In particular, R¹ , R^Two , R ^Three Is one of the halogen atoms
Is preferred. Examples of such triazine compounds include
For example, the common names are norazine, simazine, trietazine, black
Lazine, atrazine, ipazine, terbutyrazine, professional
Pazine, cyanazine, procyazine, cyprazine, meso
Prazin, Eglinazine, Proglinazine, Symmetry
, Terbutryn, dimethamethrin, desmethrin,
Metrin, metoprothrin, cyanatrine, adiproto
Phosphorus, dipropetrine, noraton, simeton, ipato
, Cebumeton, terbumeton, prometon, metmet
And atrazine [2-k].
Rollo-4-ethylamino-6-isopropylamino-
1,3,5-triazine], cyanazine [2- (4-k
Rollo-6-ethylamino-1,3,5-triazine-2
-Yl) amino-2-methylpropionitrile], pro
Pazine [2-chloro-4,6-bis (isopropylamido
No.)-1,3,5-triazine]. Active ingredient
As a combination of (I) and (II), (-) indanophor
Particularly preferred is a combination of the compound and atrazine.

The treatment amount of these active ingredients varies depending on the target crop, weed species, application scene, application conditions and the like.
Usually, the amount of indanophan or (-) indanophan of the active ingredient (I) is preferably from 1 to 4,000 g / ha, more preferably from 10 to 1,000 g / ha. The treatment dose of the active ingredient (II) varies depending on the type of compound,
For example, atrazine is preferably 10 to 10,000 g /
ha, more preferably 100 to 4,000 g / ha, and cyanazine is preferably 10 to 10,000 g / ha,
More preferably, 100 to 3,000 g / ha, and propazine is preferably 10 to 10,000 g / ha, more preferably 100 to 4,000 g / ha. In the herbicidal composition of the present invention, the content ratio of the active ingredients (I) and (II) varies depending on the target weed species, application scene, application conditions and the like, but usually preferably 1 part by weight of the component (I). On the other hand, the component (II) is in the range of 0.025 to 1000 parts by weight, more preferably 0.2 to 1: 200 parts by weight.

The herbicidal composition of the present invention can be mixed with adjuvants into various pesticide preparations according to a conventional method, and the application scene and application method are not particularly limited. The composition of the present invention can effectively control a wide range of weeds both in soil treatment and foliage treatment. In particular, major weeds in corn fields, for example, monocotyledonous plants such as barnyardgrass, enokorogosa, akinoenokorogusa, chinenokoro, crabgrass, ohishiba, shibagi, sorghum, sorghum sorghum, shatter cane, etc .; Ginseng morning glory, sea fir, American stag, American horned frog, Ebisugusa, buckwheat, Sanaetade, Sasaeadae, Suzurigyu, Shiroza, Aoagetou, Oharagarashi, Inouhouki, Sunflower, Scorpionflower Effectively control and can be safely used for corn.

The form of the herbicidal composition of the present invention may be appropriately selected depending on the target crop, the type of weeds to be controlled, the application conditions, and the like. The composition is preferably a soil treatment agent or a foliage treatment agent. The preparation method of the composition of the present invention is not particularly limited, either. The active ingredients (I) and (II) are mixed with an appropriate solid carrier or liquid carrier according to a known method, and if necessary, a surfactant, a permeating agent, Agent, spreading agent,
Solution, emulsion, wettable powder, water solvent, water dispersible granule, water dispersible granule, suspension, milk It can be made into a preparation of any dosage form such as a turbidity, a suspoemulsion, a powder, a granule and a gel. Furthermore, it is also possible to use it enclosed in a water-soluble package. During formulation, as a solid carrier,
For example, natural minerals such as kaolinite, diatomaceous earth, bentonite, synthetic hydrogenated silicon, fubasami clay, acid clay, activated carbon, sericite, talc, quartz powder, attapulgite, zeolite, etc., calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc. Inorganic salts, synthetic silicic acid, synthetic silicate, and the like. Preferred are natural minerals such as kaolinite, diatomaceous earth and bentonite.

Examples of the liquid carrier include water, alcohols (eg, methanol, ethanol, ethylene glycol, propylene glycol, isopropanol), aromatic hydrocarbons (eg, toluene, xylene, alkylbenzene, alkylnaphthalene), and ethers (eg, dioxane, diisopropyl). Ethers, butyl cellosolve, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), nitriles (acetonitrile, isobutyronitrile, etc.) ), Halogenated hydrocarbons (such as dichloroethane) and vegetable oils (such as soybean oil, rapeseed oil, cottonseed oil, castor oil and the like). Preferably, alcohols, vegetable oils and the like are used. The ratio of each carrier to the active ingredient is not particularly limited, but usually 0.1 to 10 parts by weight of the carrier per 1 part by weight of the active ingredient.

Examples of the surfactant include alkyl sulfates, alkyl aryl sulfonates, alkyl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohols Derivatives and the like. Other formulation aids include:
For example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), bentonite, lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.)
And a stabilizer such as vegetable oil, mineral oil, fatty acid, fatty acid ester and the like. In addition, the composition of the present invention can also enhance the herbicidal effect by being used in combination with other herbicides without fear of inhibiting the efficacy of the active ingredient, and furthermore insecticides, fungicides, plant regulators, It can be used in combination with fertilizers and soil conditioners.

[0015]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Formulation Examples and Test Examples, but the present invention is not limited to the following Examples unless it exceeds the gist. In the following examples, parts mean parts by weight.

Formulation Example 1 8 parts of (-)-indanophane, 40 parts of atrazine, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 47 parts of diatomaceous earth were thoroughly mixed and pulverized to obtain a wettable powder.

Formulation Example 2 10 parts of (-)-indanophane, 30 parts of cyanazine, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 55 parts of diatomaceous earth were thoroughly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 12 parts of indanophane, 60 parts of atrazine, 5 parts of polyethylene glycol dialkylaryl ether sulfate, 10 parts of calcium ligninsulfonate and 13 parts of diatomaceous earth are thoroughly mixed and pulverized, and then a small amount of water is added and stirred and mixed. The mixture is kneaded, granulated by an extrusion granulator, and dried to obtain a wettable powder.

Formulation Example 4 10 parts of (-)-indanophane, 70 parts of propazine, 5 parts of polyethylene glycol dialkylaryl ether sulfate, 10 parts of calcium ligninsulfonate and 5 parts of diatomaceous earth are thoroughly mixed and pulverized. In addition, the mixture was mixed and kneaded with stirring, granulated with an extrusion granulator, and dried to obtain a wettable powder.

Formulation Example 5 4 parts of indanophane, 20 parts of atrazine, 5 parts of calcium ligninsulfonate, 3 parts of sodium lauryl sulfate,
After 5 parts of white carbon and 62.8 parts of water were mixed and wet-pulverized, 0.2 part of xanthan gum was added and mixed and stirred to obtain a suspending agent. Next, test examples of the composition of the present invention will be described. In the following test examples, the “expected value” is the activity expected by a specific combination of two herbicides, and can be calculated from Colby's formula below. (Co
lby, SR, Weeds 15: 20-22 (1967))

[0021]

[Equation 1] E = X + Y− (XY · 100)

However, E: the herbicidal effect expected when the herbicide A is mixed with pkg / ha and the herbicide B with qkg / ha; X: the inhibition rate when the herbicide A is treated with pkg / ha; Y: suppression rate when the herbicide B was treated with qkg / ha. If the rate of inhibition when actually mixed with two kinds of herbicides exceeds this E value, it can be said that the combination shows a synergistic effect. The suppression rate was determined according to the following equation.

[0023]

## EQU2 ## Suppression rate (%) = (1−live weight of weed in treated area /
Fresh weight of weeds in untreated area) × 100

Test Example 1: Upland foliage treatment test A resin vat having an area of 200 cm ² was filled with field soil of dilapidated clay loam, and after fertilization, seeds of strawberry and enokorogusa were sown respectively, and the soil was uniformly covered. . Thereafter, cultivation management was continued in a greenhouse, and when the growth leaf age of the test weed reached the 2.0-2.5 leaf stage, each single agent of (−)-indanophane, indanophane, and atrazine was prepared according to Formulation Example 1. And the wettable powder of the mixed agent were diluted and mixed to a predetermined concentration, and uniformly processed with a small power pressurized sprayer. Thereafter, the cultivation management was continued in the greenhouse, and on the 21st day after the treatment, the above-ground living weight of each weed was measured, and the suppression rate and the expected value were obtained by the above-mentioned equations. The results are shown in Tables 1 and 2.

[0025]

[Table 1]

[0026]

[Table 2]

As is clear from Tables 1 and 2, when foliar treatment of indanophan and (-) indanophan with a single agent did not show any herbicidal effect on strawberry at the doses tested, Although it did not show a sufficient effect on Enochorosa, the combined use with atrazine showed an excellent herbicidal effect far exceeding the expected value.

Test Example 2: Upland soil treatment test In the same manner as in Test Example 1, strawberry seeds were sown in a bat, covered with soil, and
Prior to the germination of the weeds, the agents prepared in the same manner as in Test Example 1 were evenly sprayed on the soil surface. On the 21st day after drug treatment, evaluation was performed in the same manner as in Test Example 1. The results are shown in Tables 3 and 4.

[0029]

[Table 3]

[0030]

[Table 4]

As is evident from Tables 3 and 4, when the indanophane and (−) indanophane were treated with the single agent in the soil, the herbicidal effect was not shown at all at the doses tested. However, when treated in combination with atrazine, even in the case of soil treatment, an excellent herbicidal effect far exceeding the expected value was exhibited.

Test Example 3: Upland soil treatment test In the same manner as in Test Example 1, enokorogosa seeds were sown in a bat, covered with soil, and before the germination of weeds, the agent prepared in the same manner as in Test Example 1 was evenly sprayed on the soil surface. On the 21st day after drug treatment, evaluation was performed in the same manner as in Test Example 1. The results are shown in Table-5 and Table-6.

[0033]

[Table 5]

[0034]

[Table 6]

As is clear from Tables 5 and 6, when the indanophane, (-) indanophane, atrazine, and cyanazine were treated with the single agent in the soil, the herbicidal herbicide was sufficiently herbicidally controlled at the doses used in the test. Although no effect was shown, by treating indanophan or (-) indanophan in combination with atrazine or cyanazine, even in the case of soil treatment, an excellent herbicidal effect far exceeding the expected value was exhibited.

[0036]

As is clear from the test examples, the compositions of the present invention each contain a dose of indanophane or (-) indanophane which does not show a sufficient herbicidal effect when used alone, and atrazine is a triazine compound such as cyanazine. When used in combination, a synergistic effect exceeding the sum of the single effects is exhibited, a higher weed control effect can be expected, and it is possible to control weeds at a lower dose.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Osamu Ikeda Inventor: 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Yokohama, Kanagawa Prefecture Mitsubishi Chemical Corporation Yokohama Research Laboratory F-term (reference) 4H011 AB01 AB02 BA01 BA06 BB05 BB09 BC03 BC05 BC06 BC07 BC18 BC19 BC20 DA02 DA15 DA16 DD03 DD04 DH03 DH10 DH11 DH14

Claims (7)

[Claims] 1. A herbicidal composition containing the following (I) and (II) as active ingredients. (I) 2- [2- (3-chlorophenyl) -2,3-epoxypropyl] -2-ethylindane-1,3-dione or an optical isomer thereof. (II) At least one compound having a triazine skeleton and having herbicidal activity. 2. The composition according to claim 1, wherein the component (II) is a compound having a 1,3,5-triazine skeleton.
3. The herbicidal composition according to item 1. 3. The method according to claim 1, wherein the component (I) is (-)-2- [2-
(3-chlorophenyl) -2,3-epoxypropyl]
The herbicidal composition according to claim 1, wherein the composition is -2-ethylindane-1,3-dione. 4. The herbicidal composition according to claim 1, wherein the component (II) is a compound having a structure represented by the following general formula (1). Embedded image Wherein R ¹ , R ² and R ³ are each independently —AR ⁴
(A represents a sulfur atom or an oxygen atom, and R ⁴ has 1 to 1 carbon atoms.
3 represents an alkyl group and an alkenyl group having 2 to 3 carbon atoms. ^{), - NR 5 R 6 (} R 5, R 6 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, 3 carbon 6 represents a cycloalkyl group) or a halogen atom. ｝ 5. The composition of claim 2, wherein the component (II) is 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2- (4-chloro-6-ethylamino-1,
3,5-triazin-2-yl) amino-2-methylpropionitrile and 2-chloro-4,6-bis (isopropylamino) -1,3,5-triazine The herbicidal composition according to any one of claims 1 to 4, wherein: 6. The herbicidal composition according to claim 1, wherein the component (II) is contained in an amount of 0.025 to 1000 parts by weight based on 1 part by weight of the component (I). object. 7. The herbicidal composition according to claim 1, which is a foliage treating agent or a soil treating agent.