JP2907936B2 - Herbicide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a compound represented by the general formula (I): (Wherein R ₁ and R ₂ are the same or different and represent a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, or R ₁ and R ₂ together with the nitrogen atom to which they are bonded) Represents an azacycloalkane having 4 to 6 carbon atoms, A is the following formula X is a hydrogen atom, a lower alkyl group or a cycloalkyl group which may be substituted with a hydroxyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxybenzyl Represents a group, a halogen atom, a nitro group, an amino group or a trifluoromethyl group, m represents an integer of 0 to 3, n represents an integer of 0 to 2, and p and q each represent an integer of 2 to 5. The present invention relates to a herbicidal composition characterized by containing a triazole-based compound represented by the formula (1) and pyrazosulfuron-ethyl and dimelone as active ingredients. A herbicide which has a herbicidal spectrum and further has a compound represented by the general formula (I), which is a component of the herbicide of the present invention, which has significantly reduced phytotoxicity to rice under adverse conditions such as sandy loam. It relates to a composition.

[Problems to be solved by conventional technology and invention]

The compound represented by the general formula (I) is a compound invented by the present inventors and described in Japanese Patent Application Laid-Open No. 2-1481 filed earlier, which is represented by the general formula (I). It is described that the compound exhibits an excellent herbicidal effect on foxglove and the like. Further, pyrazosulfuron-ethyl is disclosed in JP-A-59-12248.
8. This compound is described in JP-A-59-219281, and it is described that this compound is effective at a very low dose in broadleaf weeds, Spodoptera mori and Urikawa.

Daimron is a compound described in JP-B-48-35454, which is known to be highly effective against Cyperaceae weeds such as fireflies and sedges.

By the way, the compound represented by the general formula (I) has a weak herbicidal effect on a growing broadleaf weed or a cyperaceae weed, and a high dose is required to show a sufficient effect. In addition, there are problems such as the possibility of chemical damage to rice under adverse conditions represented by extremely loamy sandy loam.

Further, pyrazosulfuron-ethyl has a low herbicidal activity against the rice millet, and often shows phytotoxicity to rice when the dose is further increased. Daimron also has almost no effect on sand millet and broadleaf weeds, and there are various problems when used alone.

On the other hand, the usefulness of the composition of pyrazosulfuron-ethyl and thyrone is disclosed in JP-A-62-56406, but the combination is particularly effective in the present invention. No mention is made of the use of the compound represented by the general formula (I) in combination, and the composition of pyrazosulfuron-ethyl and Daimrone exhibits a high herbicidal effect on most weeds in the early stage of weed development. However, it is difficult to completely kill the rice flour, and there is a problem that the herbicidal effect is extremely low especially for the mature rice flour.

Further, the composition of the compound represented by the general formula (I) and pyrazosulfuron-ethyl is disclosed in European Patent Publication No. 0332133, but there is no mention of the combination of the composition of the present invention. Absent. Further, the composition described in European Patent Publication No. 0332133 is intended to have a synergistic herbicidal activity, and does not specifically describe a phytotoxicity-reducing effect.

In recent years, the occurrence of perennial weeds such as sea bream, which is a strongly harmful weed in paddy fields, broadleaf weeds, shrubs, fireflies, and urikawa, has become a problem. Tend not to be expected. For this reason, the same or different herbicides must be used several times or in large quantities, and many problems such as phytotoxicity to rice and soil persistence are raised as well as labor and cost. .

[Means for Solving the Problems] As a result of intensive studies to solve the above problems, the present invention has found that a composition comprising a compound represented by the general formula (I) and pyrazosulfuron-ethyl and Daimulon as active ingredients Surprisingly, however, a broad herbicidal spectrum was obtained beyond the application range obtained for each of them alone, and a high effect was also obtained on the high-leaved stage of the Japanese millet. In addition, the present invention has found a completely unpredictable usefulness, such as showing a remarkable herbicidal effect at a low dose without giving substantial phytotoxicity to rice and having a long-lasting efficacy. Furthermore, it was also found that the paddy field showed a phytotoxicity-reducing effect on rice under bad conditions, and the present invention was achieved.

General formula (I) which is one of the active ingredients of the mixture of the present invention
The compound represented by the general formula (II) (Wherein A and n have the same meanings as described above). (Wherein Y represents a halogen atom, and R ₁ and R ₂ represent the above-mentioned meanings), and oxidized with an appropriate oxidizing agent if necessary.

In the above reaction, the target compound I is a sulfinyl compound (n = 1) or a sulfonyl compound (n =
In case 2), a compound of formula II in which the S moiety has been similarly oxidized may be used as the starting material, or
To produce a compound of formula I, which is not oxidized, which may be oxidized if necessary. Oxidized or unoxidized compound II
The step of reacting with III is at least 1 equivalent, preferably 1 to 2 equivalents, preferably 1 to 1.2 equivalents in a suitable solvent in the presence of 1 to 2 equivalents of a deoxidizing agent relative to compound II. The compound III is reacted. The reaction temperature is 0-100 ° C, preferably 20-70 ° C.
C is appropriate. Here, as the deoxidizing agent, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate,
Inorganic bases such as sodium hydride, organic bases such as triethylamine and pyridine, or solvents such as hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, diethyl ether, tetrahydrofuran and dioxane Ethers, ketones such as acetone and methyl ethyl ketone, and other solvents such as ethyl acetate, acetonitrile, dimethylformamide, pyridine, dimethyl sulfoxide, and water, or a suitable mixed solvent thereof.

The oxidation step can be performed, for example, by oxidizing with an oxidizing agent in a suitable solvent.

As the oxidizing agent used here, hydrogen peroxide, potassium permanganate, inorganic oxidizing agents such as chromic acid, peracetic acid,
Organic oxidizing agents such as m-chloroperbenzoic acid can be mentioned, and examples of the solvent used in this case include methylene chloride, chloroform, acetone, acetic acid, water and the like, or a mixed solvent thereof. The reaction temperature is suitably from 0 to 50 ° C, but may be appropriately heated or cooled depending on the type of solvent or the progress of the reaction.

Among the compounds represented by the general formula (I) thus obtained, a preferred embodiment of the mixture of the present invention is represented by the general formula (IV) (Wherein X and m represent the same as described above), and more preferably a compound represented by the formula (V) Equation (VI) And the like.

Further, pyrazosulfuron-ethyl as an active ingredient of the mixture of the present invention has the formula And can be obtained, for example, by the method described in JP-A-59-122488.

Daimlon has the formula And can be obtained, for example, by the method described in JP-B-48-35454.

The admixture according to the invention is a novel combination which has not been described in the literature, and of course there is no literature which mentions its specific enhancement of potency.

The effect according to the present invention is observed in a wide range of mixing ratio,
With respect to 1 part by weight of the compound represented by the general formula (I), 0.01 to 10 parts by weight of pyrazosulfuron-ethyl and 0.
Useful herbicides can be made by mixing 1 to 20 parts by weight. The herbicide of the present invention thus obtained has high effects by soil treatment before and after germination of weeds, and can be used safely without substantially damaging rice.

The mixture of the present invention may spray the active ingredient itself,
Mixable with various solid and liquid carriers used in general pesticide preparations for more convenient use, wettable powders, emulsions,
It can be manufactured into oils, powders, granules, flowables and the like. Further, auxiliary agents such as dispersants, diluents, emulsifiers, spreading agents, wetting agents, adsorbents, thickeners, defoamers, antifreezing agents and the like can be added to the drug.

The carrier mentioned here may be either solid or liquid,
Also, a combination of these may be used. Here are some examples:
Talc, clay, bentonite, kaolin, diatomaceous earth,
Examples include calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene, cyclohexane, methylnaphthalene, benzene, acetone, dimethylformamide, glycol ether, N-methylpyrrolidone, and the like.

Examples of the auxiliary agent include polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate esters, petroleum oil Sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonic acids, aliphatic amine salts, quaternary
Grade mammonium salts, alkylpyridinium salts, alkyldimethyl betaine, alkylaminoethylglycine, polyglycol sulfate, alkylaminesulfonic acid, isopropyl phosphate, carboxymethylcellulose, polyvinyl alcohol, hydroxypropylcellulose, ethylene glycol, xanthan gum, etc. Can be

In formulating, the mixing ratio can generally be freely selected from 0.05% to 95% by weight of the mixture of the present invention, but preferably contains 0.5 to 70%, Carrier is 1-99%, preferably 40-90%, adjuvant is 0%
Formulations containing -20%, preferably 1-7%, are preferred.
In addition, a wider range of effects can be expected by mixing and using other fungicides, pesticides such as herbicides, plant growth regulators, insecticides, acaricides, and fertilizers.

When actually using the mixture of the present invention, it is known to those skilled in the art that the amount to be used is appropriately selected depending on the time of use, weather conditions, method of use, form of use, place of use, target weed, target crop, etc. As is evident, the dosage used is generally from 5 to 500 g per 10 ares, preferably from 10 to 300 g per 10 arms, as the admixture according to the invention.

 Next, the usefulness of the present invention will be specifically described with reference to test examples.

Test Example 1 Fill paddy soil into a 1/5000 arel Wagner pot,
Water was added for padding, and seeds of red foxtail, annual broadleaf weeds (Azena, Kikasigusa, Mizohakobe) and fireflies were sown, tubers of Mizugayatsuri and Urikawa were planted and flooded to 3 cm.

Eleven days after weed sowing, a predetermined amount of the granules obtained according to Preparation Example 1 described below was hand-sprayed on the water surface. Management and rearing were performed in a greenhouse, and the herbicidal effect was investigated 20 days after the chemical treatment. Table 1 shows the results.

In addition, the numerical value in a table | surface shows the weeding effect, and it is as follows specifically.

Numerical value Herbicidal effect 5 Herbicidal rate 90% or more (almost completely dead) 4 Herbicidal rate 70-89% 3 Herbicidal rate 40-69% 2 Herbicidal rate 20-39% 1 Herbicidal rate 6-19% 0 Herbicide 5% or less (Almost no effect) Test Example 2 Fill paddy soil into a 1/5000 are Wagner pot,
Water was added to the plants, and rice plants at the 2 leaf stage were transplanted to a depth of 1 cm and submerged to 3 cm.

One day after transplanting the rice, a predetermined amount of a wettable powder manufactured according to Preparation Example 2 described below was diluted to 5 ml and dropped into a pot. Management and cultivation were performed in a greenhouse, and 30 days after chemical treatment, the above-ground live weight of rice was measured to determine the ratio of the untreated group to the plant. The results are shown in Table 2.

Test Example 3 20 rice seeds were placed on a petri dish having an inner diameter of 9 cm, and for each compound, 20 ml of a water diluent adjusted to a predetermined concentration was added, and the mixture was placed in a thermostat at 25 ° C., an illuminance of 500 Lux, and light and dark for 12 hours to 12 hours. For 10 days.

In the survey, the first true leaf length was measured, and the ratio to the untreated section was determined. Table 3 shows the results.

Test Example 4 Field Test A paddy field was divided into 10 m ² in one section, and 2.5-leaf rice was planted (transplant depth: 1 cm).

The weeds are the foxtail, the annual broadleaf weed (Kikasigusa,
Azena, Mizohakobe) and firefly seeds were sown, and tubers of Mizugayatsui and Urikawa were mixed.

For the treatment of the drug, a predetermined amount of the wettable powder obtained according to Formulation Example 2 to be described later was diluted with water 3 days and 14 days after rice transplantation, and the entire surface was uniformly flooded with Joro. The water depth should be between 3 and
It was kept at 5 cm.

The survey was performed by observation 30 days after drug treatment. The results are shown in Tables 4 and 5. The numerical values in the table indicate the herbicidal effect and the phytotoxicity on rice, and the herbicidal effect is the same as that shown in Test Example 1.
It is as follows.

Numerical value Rice phytotoxicity 0 None 1 Slight harm 2 Low harm 3 Moderate harm 4 Major harm 5 Serious harm Next, preparation examples of the herbicidal composition of the present invention will be described.

Formulation Example 1 Granules Compound of formula (V) 1 part by weight Pyrazosulfuron-ethyl 0.1 Daimulon 2 Sodium ligninsulfonate 2 Bentonite 20 Clay 74.9 These components are mixed well until uniform, and granulated to obtain granules .

Formulation Example 2 wettable powder 10 parts by weight of the compound of formula (VI) pyrazosulfuron-ethyl 1 Daimulon 20 sodium alkyl sulfate 2.5 polyoxyethylene alkyl phenyl ether 2.5 clay 64 These components are thoroughly mixed until uniform, and finely pulverized. To obtain a wettable powder.

Continued on the front page (51) Int.Cl. ⁶ identification code FI A01N 47:30) (58) Investigated field (Int.Cl. ⁶ , DB name) A01N 47/38 A01N 47/36 A01N 47/30 CA ( STN)

Claims (1)

(57) [Claims] (1) General formula (Wherein R ₁ and R ₂ are the same or different and represent a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, or R ₁ and R ₂ together with the nitrogen atom to which they are bonded) Represents an azacycloalkane having 4 to 6 carbon atoms; X is a hydrogen atom, a lower alkyl group or a cycloalkyl group which may be substituted with a hydroxyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxybenzyl Represents a group, a halogen atom, a nitro group, an amino group, or a trifluoromethyl group, m is an integer of 0 to 3, n is an integer of 0 to 2, p and q are each 2 to 5
Represents an integer. A) a triazole compound represented by the formula:
A herbicidal composition characterized by containing pyrazosulfuron-ethyl and Daimulon as active ingredients.