JPH0495002A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicidal composition, containing a triazine derivative and an imidazolinone-based herbicide as active ingredients, capable of exhibiting high effects in a small amount of chemical and simultaneously having a broad weeding spectrum and a wide range of a suitable period for treatment with the chemical without causing phytotoxicity in crops. CONSTITUTION:A herbicidal composition containing a compound expressed by formula I [A is group expressed by formula II (Z is O or S) or formula III (X<2> is CH3 or F; n us 0-2); R<1> is H or CH3; X<1> is F or Cl] and a compound expressed by formula IV (B is group expressed by formula V, etc.) at (10:1)-(1:100) weight ratio as active ingredients. The aforementioned composition is used by mixing the active ingredients with a liquid carrier or a solid carrier and preparing the resultant mixture into a formulation such as wettable powder, emulsion, dust, granule, flowable or solution. The above-mentioned composition is capable of exhibiting excellent effects by treating soil or leaves and stems of farmland crops such as corn, wheat or barley before or after germination of weeds. Furthermore, the effects are exhibited even on perennial weeds in orchards or non-crop land.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a herbicidal composition containing a triazine derivative and an imidabrinone herbicide as active ingredients.

[Prior art and problems to be solved by the invention] Various herbicides have been developed so far and have contributed to agricultural productivity and labor saving. However, as certain herbicides have been used for many years, there has been an increase in the number of weeds that are difficult to control and to which these herbicides are not effective. It is hoped that a new drug will emerge. Furthermore, in order to solve the problem of environmental pollution caused by conventional herbicides, the development of highly active herbicides is also desired. Furthermore, in order to deal with the uneven emergence of weeds over a long period of time, we are developing a weed control method with excellent residual effect and a wide range of suitable treatment periods that are effective even when treated over a wide range of periods from before weed emergence to the growing season. The emergence of a drug is also awaited.

Under these circumstances, the present inventors discovered that a specific novel haloalkyl-containing triazine derivative does not cause chemical damage to grass field crops and has high herbicidal properties against difficult-to-control weeds in both soil and foliage treatments. It has been found that the compound is effective and has an excellent effect on treating flooded soil (Japanese Patent Application Nos. 1-38178 and 1-154465). The present inventors have conducted repeated studies to further improve the herbicidal activity of the triazine derivatives.

[Means to solve the problem]

As a result, compositions that combine the triazine derivatives with specific imidazolinone herbicides exhibit superior herbicidal activity that cannot be expected from the properties of each individual herbicide, exhibiting high herbicidal effects at lower dosages and a wide range of herbicidal effects. They discovered that it has a herbicidal spectrum and completed the present invention.

That is, the present invention (wherein, X2 represents a methyl group or a fluorine atom, and n
represents an integer between θ and 2. ), R1 represents a hydrogen atom or a methyl group, and Xl represents a fluorine atom or a chlorine atom. The present invention provides a herbicidal composition containing as active ingredients a triazine derivative represented by the following: and an imidazolinone herbicide represented by the following:

Specific examples of the triazine derivatives represented by the general formula CI) include 2-amino-4-[l(benzofuran-2
°-yl)ethylamino]6-(α-fluoro, α-methylethyl)-S-triazine2-amino-4-(1-(benzofuran-2yl)ethylamine)-6-(α-fluoroethyl 2-amino 4-
(1-(benzothiophen-2-yl)ethylamino)-6-(α-fluoro.

α-methylethyl)-s-triazine2-amino-4-(α-fluoro, α-methylethyl)
-6-(2-(3',5'-dimethylphenoxy)-1
-methyl-ethylamino)-S-) riazine 2-amino-4-(α-fluoro, α-methylethyl)
-6-(2-(3°-fluorophenoxy)-1-methyl-ethylamino)-8-)riazine 2-amino-4-
(α-chloro, α-methylethyl)-6-(2-(3°
, 5'-dimethylphenoxy)-1-methyl-ethylamino)-S-) riazine 2-amino-4-(α-chloro, α-methylethyl)-
6-(2-(3',5'-dimethylphenoxy)-1-
Examples include methylethylamino)-s-1 riazine.

The triazine derivative represented by the above general formula (I) can be produced by various methods. Among them, as an efficient manufacturing method, the general formula % formula % [[] [wherein A is the same as above. X3 represents a halogen atom.

] A salt of an alkylamine represented by H and the formula H2N-C-N
By reacting cyanoguanidine represented by H-CN [
In the formula, A and X3 are the same as above. ] and then converting the alkyl biguanide salt to the general formula CH.

R' -C-C00R2 XI...(V) [In the formula, R' and Xl are the same as above. R2 has 1 carbon number
~4 alkyl group is shown. ] A method of reacting an alkyl ester represented by the following can be mentioned.

According to this, a salt of an alkylamine represented by the general formula CI) is reacted with cyanoguanidine to obtain a salt of an alkyl biguanide represented by the general formula (IV), which is then combined with an alkyl ester represented by the general formula (V). By reacting, the desired triazine derivative represented by the general formula CI) can be efficiently obtained.

In the reaction between the alkylamine salt represented by the above general formula (III) and cyanoguanidine, both compounds may be used in approximately equimolar proportions, and the solvent may be a cyclic hydrocarbon such as benzene, decalin, alkylnaphthalene, etc. Furthermore, carbon tetrachloride, ethylene dichloride, tetralobenzene,
Dichlorobenzene.

Chlorinated hydrocarbons such as trichlorobenzene and the like can also be used. Further, the reaction temperature is not particularly limited, and the reaction progresses satisfactorily at a temperature ranging from low to high temperatures, specifically in the range of 80 to 200°C.

Through this reaction, a salt of the alkyl biguanide derivative represented by the general formula (IV) is obtained, and by reacting this with an alkyl ester of the general formula (V), the desired general formula C
A triazine derivative represented by I) is produced. This reaction usually uses methanol.

Alcohols such as ethanol and isopropanol, various ketones, aliphatic hydrocarbons, and various ethers.

The process proceeds efficiently in a solvent such as various cyclic hydrocarbons and chlorinated hydrocarbons in the presence of a catalyst such as a base at about 10 to 100°C.

Furthermore, these compounds have optical isomers, and are usually obtained as racemates, or each enantiomer can be obtained by known methods such as asymmetric synthesis.

In the present invention, racemates or individual optical isomers can be used. Furthermore, in the present invention, salts of inorganic acids or organic acids can also be used.

On the other hand, as a specific example of the imidazolinone herbicide represented by the above general formula (I[), methyl-6(4-isopropyl-4-methyl-5-oxo-2-imidabrinone-2
-yl)-m-) toluate and methyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolinon-2-yl)p-toluate and 2-(4-
Mention may be made of isopropyl-4-methyl-5-oxo-2-imidazolinon-2-yl)nicotinic acid.

The imidazolinone herbicide represented by the above general formula [II] can be obtained by a known production method. Also,
You may use what is commercially available.

These imidazolinone herbicides are highly effective against grass weeds. It is also effective against broad-leaved weeds.
It is also used in wheat, barley fields, and non-agricultural land.

The herbicide composition of the present invention contains a triazine derivative represented by the above general formula [■] and an imidazolinone herbicide represented by the above general formula (II) as active ingredients, and the blending ratio thereof is particularly determined. There are no restrictions and excellent synergistic effects can be obtained in a wide range of compounding ratios. Usually, it is preferable to mix the triazine derivative:imidazolinone herbicide within the range of 10:1 to 1:100 (weight ratio).

The herbicidal composition of the present invention is prepared by mixing a triazine derivative represented by the above general formula CI) and an imidazolinone herbicide represented by the above general formula CII) with a liquid carrier such as a solvent or a solid carrier such as mineral powder. It can be used in the form of formulations such as wettable powders, emulsions, single powders, flowable preparations, and liquid preparations. When formulating, emulsifiers, surfactants such as dispersants, spreading agents, suspending agents, penetrating agents, and stabilizers may be added as desired.
Other adjuvants may be added.

When the herbicide composition of the present invention is used in the form of a wettable powder, the above-mentioned triazine derivative and imidabrinone herbicide are usually used as active ingredients in an amount of 10 to 55% by weight and a solid carrier of 40 to 40% by weight.
A composition may be prepared by blending 88% by weight of the surfactant and 2 to 5% by weight of the surfactant, and then used. When used in the form of an emulsion or a flowable agent, the active ingredients are usually 5 to 50% by weight of the above-mentioned triazine derivative and imidabrinone herbicide, 35 to 90% by weight of a solvent, and 5 to 15% by weight of a surfactant and other adjuvants. What is necessary is just to mix|blend and prepare in the ratio of weight%.

On the other hand, when used in the form of a powder, it is usually prepared by blending the above-mentioned triazine derivative as an active ingredient, 1 to 15% by weight of the imidazolinone herbicide, and 85 to 99% by weight of the solid carrier. Furthermore, when used in the form of granules, the above-mentioned triazine derivative and imidabrinone herbicide as active ingredients, 0.1 to 15% by weight, and 80% by weight of a solid carrier.
It may be prepared by blending the surfactant in a proportion of 97.9% by weight and 2 to 5% by weight of the surfactant. Here, fine mineral powder is used as the solid carrier, and this fine mineral powder is
Oxides such as diatomaceous earth and slaked lime, phosphates such as apatite, sulfates such as ceracola, and talc.

Pyroferrite, clay, kaolin, bentonite,
Acid clay, white carbon, quartz powder.

You can also use silicates such as silica powder.

In addition, liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, and spindle oil, aromatic hydrocarbons such as benzene, toluene, and xylene, and chlorinated hydrocarbons such as 0-chlorotoluene, trichloromethane, and trichloroethylene. , alcohols such as cyclohexanol, amyl alcohol, ethylene glycol, alcohol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, isophorone,
Ketones such as cyclohexanone, cyclohexenyl-cyclohexanone, butyl cellosolve.

Organic solvents such as ethers such as dimethyl ether and methyl ethyl ether, esters such as isopropyl acetate, benzyl acetate, and methyl phthalate, amides such as dimethylformamide, nitrites such as acetonitrile and propionitrile, sulfoxides such as dimethyl sulfoxide, or mixtures thereof. Or you can give them water, etc.

Furthermore, as a surfactant, anionic type (alkylbenzene sulfonate, alkyl sulfonate, lauric acid amide sulfonate, etc.) is used.

Nonionic type (polyoxyethylene octyl ether, polyethylene glycol laurate, sorbitan alkyl ester, etc.), cationic type (dimethyllaurylbenzylammonium chloride, laurylamine, stearyltrimethylammonium chloride, etc.), or zwitterionic type (amino acids, betaine, etc.) You can also use

In addition, sodium alginate is added to the herbicide composition of the present invention for the purpose of improving the properties of the preparation and increasing the herbicidal effect.

A polymer compound such as carboxymethylcellulose, carboxyvinyl polymer, gum arabic, hydroxypropylmethylcellulose, or an adjuvant can also be used in combination.

The herbicide composition of the present invention can be applied to field crops such as corn, sorghum, wheat, barley, and oats by soil or foliage treatment before or after the germination of weeds, allowing it to be highly selective and free from phytotoxicity. It exhibits excellent effects as a herbicide. In addition, it has a high weeding effect on not only annual weeds but also perennial weeds, and it is also effective in orchards and non-agricultural lands (industrial areas, railway sites, roadsides, riverside sites, fallow lands).
It also exhibits excellent control effects against weeds, etc., by treating them with soil or foliage.

The herbicide composition of the present invention has an active ingredient of o per lθ are.
, t-to, o o o g or so, preferably 1~
Apply 1,000g. In addition, when spraying on plant stems and leaves, the concentration is about 1 to 100,000 ppm, preferably 10 to 100,000 ppm.
Apply diluted to 10.000 flpm.

In addition, the herbicidal composition of the present invention can also be used in combination with other herbicidal components. Examples of herbicidal ingredients that can be used here include diphenyl ether-based and triazine-based herbicides, which are conventionally commercially available herbicides.

Examples include phenoxyacetic acid type, carbamate type, thiol carbamate type, acid anilide type, pyrazole type, phosphoric acid type, sulfonylurea type, dinitroaniline type, bromoxynil, ioxynil, and oxacyacin.

Furthermore, the herbicidal composition of the present invention can be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, etc., if necessary.

〔Example〕

Next, the present invention will be explained by examples.

First, the formulation method will be specifically explained using formulation examples. In addition, the following "manufacturing side middle part" means % by weight. The compounds shown in Table 1 were used as triazine derivatives (compound A), and the compounds shown in Table 2 were used as imidazolinone herbicides (compound B).

Table 1 Table 1 (Continued) Table 1 (Continued) Table 2 Production Example 1 Wettable powder Compound A - 15 parts Compound B - 115 parts Diatomaceous earth 62 parts White carbon 15 parts Sodium alkylbenzenesulfonate 2 parts Lignin sulfone At least 1 part of acid soda was mixed and pulverized uniformly to obtain 100 parts of a wettable powder.

Formulation Example 2 Emulsion Compound A - 210 parts Compound B - 230 parts Xylene 20 parts Dimethylformamide 20 parts Tulpol 2
20 parts of 806B (manufactured by Toho Chemical Industries, surfactant) The above components were uniformly dissolved and mixed to obtain 100 parts of an emulsion.

Formulation Example 3 Powder Compound A-30, 6 parts Compound B-1 1.4 parts Diatomaceous earth 20 parts Talc
78 parts or more were mixed and uniformly mixed and pulverized to obtain 100 parts of a powder.

Formulation Example 4 Granules Compound A - 51 parts Compound B - 23 parts Bentonite 30 parts Talc 63 parts Sodium ligninsulfonate 3 parts or more were thoroughly mixed, mixed and pulverized uniformly, and water was added and kneaded well.
The granulation was dried to obtain 100 parts of granules.

Formulation Example 5 Flowable agent Compound A - 710 parts Compound B - 115 parts Methyl cellulose 0.3 parts Colloidal silica 1.5 parts Sodium ligninsulfonate 1 part Polyoxyethylene nonyl 2 parts Phenyl ether water 70
．． Two or more parts were thoroughly mixed and dispersed, and the slurry mixture was wet-pulverized to obtain 100 parts of a stable flowable agent.

Formulation Example 6 97 parts of clay (trade name: Nidikrite, manufactured by Zeeklite Industries) as a wettable powder carrier, 5 parts of alkylaryl sulfonate (trade name: Neoperex, manufactured by Kao Atlas Co., Ltd.) as a surfactant, and 1.5 parts of nonionic and anionic surfactants (trade name: Solpol 800A, manufactured by Toho Chemical Industry Co., Ltd.) were uniformly ground and mixed to obtain a carrier for a wettable powder.

90 parts of this wettable powder carrier and 10 parts of the triazine derivatives (compounds A-1 to A-7) shown in Table 1, or the imidabrinone herbicides (compounds B-1 and B-7) shown in Table 2.
2) 10 parts were uniformly ground and mixed to obtain a wettable powder.

Furthermore, the carrier for a wettable powder containing the triazine derivative obtained above and the carrier for a wettable powder containing an imidazolinone herbicide are mixed in a predetermined amount (active ingredient ratio), uniformly mixed and pulverized, and then I got Japanese medicine.

Example 1 Growing Season Treatment Test A 1/2000 are Wagner pot filled with upland soil was planted with Psyllium japonica and Yaemugura.

After sowing and covering soil with weed seeds such as weed grass and violet and crop seeds of wheat, barley, and oats, they were grown in a greenhouse, and the above formulation example was applied at the 1.5 to 2.5 leaf stage of these weeds and the 3 leaf stage of the crops. A predetermined amount of the herbicide obtained in step 6 was suspended in water, and
A liquid volume equivalent to 07/10 are was uniformly sprayed onto the stems and leaves. Thereafter, the plants were grown in a greenhouse, and on the 20th day after treatment, the crop damage and herbicidal effect were evaluated according to the following criteria.

The results are shown in Table 3.

(Judgment criteria) Degree of herbicidal effect Herbicidal effect (weed killing rate) Less than 5% (hardly no effect) 5-20% 20-40% 40-70% 70-80% 90% or more (almost completely However, the above herbicide rate was determined by measuring the weight of above-ground plants in the chemical-damaged area and the weight of above-ground plants in the non-treated area using the following formula.

Degree of phytotoxicity 0... No phytotoxicity to crops was observed 1...
...Hardly any chemical damage to crops was observed2...
...Some chemical damage to crops is observed 3...
・Phytotoxicity to crops is observed 4... Phytotoxicity to crops is noticeably observed 5... Crops are almost dead Table 3 Some excerpts from the results shown in Table 3 are as follows. The synergistic effect of triazine derivatives and imidazolinone herbicides was investigated using the method described in the following.

[Source: Limpel, L, E,, P, H, 5chu
ldt and t, amont.

Proc, NEWCC, 16, 48-53 (196
2)) Here, the actual value (herbicide rate) of the herbicide obtained by mixing the triazine derivative and the imidazolinone herbicide is Q.
If it is larger than t, it means that a synergistic effect has been expressed in herbicidal activity. The results are shown in Table 4.

Example 2 Soil Treatment Test Weed seeds of crabgrass, morning glory, and Japanese crocodile were sown in a 1/2000 are Wagner pot filled with upland soil. Before weeds germinate, a predetermined amount of the herbicide obtained in Formulation Example 6 above was suspended in water, and the soil surface was uniformly sprayed with a liquid volume equivalent to 100A/10A. after that,
Example 1: Cultivated in a greenhouse and tested for herbicidal effect 30 days after treatment
Judgment was made according to the same criteria. The results are shown in Table 5.

Table 5 Example 3 Field test (soil treatment test) A test plot with an area of 1 plot or 2 m was prepared, and weed seeds of sagebrush, japonica, chickweed, violet, chamomile, violet, poppy, and chrysanthemum, and crops of wheat and barley were prepared. Seeds were sown at the same time.

Thereafter, before wheat, barley and weeds germinate, a predetermined amount of the herbicide diluted solution obtained in Formulation Example 6 above is added to 2C1j'/
A liquid amount equivalent to 10 ares was uniformly sprayed on the soil surface. This test was conducted in triplicate.

After 60 days of spraying, the remaining weeds were cut off from the ground, their fresh weight was measured, and the average weeding rate for the three plots was calculated using the following formula.

In addition, for wheat and barley, the fresh weight of above-ground parts was measured in the same manner as for weeds, and the degree of chemical damage (suppression rate) was determined. 6th result
Shown in the table.

Example 4 Field test (growing season treatment test) A test plot with an area of 2 rri was created, and weed seeds of sagebrush, japonica, chickweed, violets, chamomile, violet, chinese poppy, and chrysanthemum and crop seeds of wheat and barley were grown. Sowed at the same time.

After that, weeds reach the 2-3 leaf stage and wheat and barley reach the 3-leaf stage.
When the leaf stage was reached, a predetermined amount of the diluted herbicide obtained in Production Example 6 was uniformly sprayed on the foliage in a liquid volume equivalent to 20 n/10 are.

Thirty days after the chemical spraying, the herbicidal rate and the degree of chemical damage were determined using the same method as in Example 3. The results are shown in Table 7.

〔Effect of the invention〕

The herbicide composition of the present invention has a synergistic effect between its active ingredients, the triazine derivative and the imidazolinone herbicide.
It exhibits high herbicidal effects at low doses and has a wide herbicidal spectrum. In addition, when used as a herbicide for upland fields, the range of suitable chemical treatment is wider than that of existing herbicides for upland fields, and for difficult-to-control weeds, soil treatment before or at the time of weed germination can also be applied during the weed growth period. It also shows high activity in foliar and foliage treatments, and does not cause any chemical damage to crops.

In particular, the effect is extremely high when applied to soil or foliage treatments in fields of gramineous crops. In addition, it exhibits excellent herbicidal effects on not only annual weeds but also perennial weeds in orchards and non-agricultural land, with a wide herbicidal spectrum at low doses.

Claims (1)

[Claims] General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, A is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, Z represents an oxygen atom or a sulfur atom.) or ▲
There are mathematical formulas, chemical formulas, tables, etc.▼ (However, X^2 represents a methyl group or a fluorine atom,
n represents an integer of 0 to 2. ), R^1 represents a hydrogen atom or a methyl group, and X^1 represents a fluorine atom or a chlorine atom. ] Triazine derivatives represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, B is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas , chemical formulas, tables, etc. Show ▼. ] A herbicide composition containing an imidazolinone herbicide represented by the following as an active ingredient.