JPS5812244B2 - herbicide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a herbicidal composition, and more particularly, the present invention relates to a herbicidal composition containing a specific N-(α·α-dialkylpenzyl)phenylacetamide derivative, which is a new compound, and 3-(2·4-dichloro-5 -isopropoxyphenyl)5-1-butyl-1,3,5-
The present invention relates to a herbicide composition with excellent herbicidal effects containing oxadiazole-2(3H) monoone as an active ingredient.

Currently, various herbicides are used in rice cultivation, etc., but most of them target annual weeds.

As a result, perennial weeds that are not effective have flourished, and their control has become a problem.

In addition, many of the rice field weeds are characterized by their emergence over a long period of time and at different times, and the growth status of the weeds at the time of herbicide application varies from ungerminated to somewhat well-grown. There is usually a mixture of stages.

For this reason, it is not possible to control the herbicide sufficiently by spraying the herbicide once, and it is necessary to spray the same type of herbicide or different types of herbicide several times.

However, spraying such a large amount of herbicide several times requires a lot of labor, and there are problems in terms of economics and chemical residue.

Therefore, the present inventors solved the above-mentioned problems of the conventional technology, and by spraying a low dose of herbicide once, it is possible to sufficiently control from ungerminated annual weeds to well-grown annual weeds and perennial weeds. We conducted extensive research to develop a herbicide that could.

In the course of this research, the present inventors succeeded in producing a specific N-(α・α-dialkylpenzyl)phenylacetamide derivative, which is a new compound, and also demonstrated that this new compound is useful as a herbicide. (Japanese Patent Application Laid-open Nos. 104240/1982 and 110655/1983).

However, when this new compound is used alone as a herbicide, it has a high herbicidal effect on grasshopper, annual cyperus, as well as perennial pine beetle, bulrush, water snail, etc. in the early stage of growth, and is highly safe for paddy rice.
Subsequent research has revealed that once the weeds have grown to a certain extent, they are not effective enough to kill weeds in general, including field weeds.

Therefore, the present inventors conducted research focusing on resolving the drawbacks of the above-mentioned new compound as a herbicide.
・4-dichloro-5-impropoxyphenyl) 5-t
-Butyl-1,3,4-oxadiazole-2(3H)
It is expected that by using I-ON in combination, all ungerminated annual and perennial weeds that have grown to some extent can be controlled almost completely and over a long period of time, at low doses and completely harmless to paddy rice. We have discovered that an extremely excellent synergistic effect can be obtained.

When the above-mentioned 3-(2,4-dichloro-5-isopropoxyphenyl)5-t-butyl-1,3,4-oxadiazole-2(3H) monoone is used alone,
Although it is somewhat effective against annual cyperus, annual broad-leaved weeds, and pine grass in the pre-rice planting and early growth stages, it is significantly less effective against weeds that have advanced to a certain stage of growth. be.

The herbicidal composition of the present invention exhibits a remarkable synergistic effect by combining two components, each of which has drawbacks when used alone, as active ingredients.

The present invention was completed based on this knowledge.

That is, the present invention provides an N-(α −
The active ingredients are α-dialkylbenzyl)phenylacetamide derivative and 3-(2,4-dichloro-5-isopropoxyphenyl)5-t-butyl-13,4-oxadiazole-2(3H) monoone. The present invention provides a herbicide composition that does the following:

As described above, the herbicide composition of the present invention has as one of the active ingredients a compound represented by the structural formula, a compound represented by the structural formula, a compound represented by the structural formula, a compound represented by the structural formula, and a structural formula. selected from the group consisting of compounds represented by 赳N1(α-
An α-dialkylbenzyl)phenylacetamide derivative is used.

The compounds represented by the above structural formulas (I) to (V) can be produced by various methods, but they are usually produced by JP-A-55
-104240 Publication and JP-A-56-110655
It is manufactured by the method disclosed in the publication.

Here, even if the N-(α・α-dialkylbenzyl)phenylacetamide derivative represented by any of the above structural formulas (I) to (V) is used alone or in combination, weeds can grow to a certain extent. At the advanced stage, the herbicidal effect is not sufficient, and 3-(2.4-
The object of the present invention can be achieved by using it in combination with dichloro-5-impropoxyphenyl) 5-t-butyl-13,4-oxadiazole-2(3H) monoone.

Next, the other active ingredient of the herbicide composition of the present invention, 3-(2,4-dichlororuinpropoxyphenyl) 5
-t-butyl-1,3,4-oxadiazole-2(3
H) Oneon is a well-known herbicide that is widely used.

There is no particular restriction on the blending ratio of the above-mentioned two active ingredients in this herbicide composition, and an excellent synergistic effect can be obtained in a wide range of blending ratios, but preferably, the above-mentioned structural formula (I)
A new N-(α・α-
3-(2,4-dichloro-5-ingropoxypheni#)5-t-butyl-1,3,4-oxadiazole-2(3H) monoone per 1 part by weight of dialkylbenzylphenylacetamide derivative 0.1 to 10 parts by weight.

The herbicidal composition of the present invention is prepared by mixing the two active ingredients with a liquid carrier such as an organic solvent or a solid carrier such as fine mineral powder, and formulating it in the form of a wettable powder, emulsion, powder, granular powder, etc. can be used.

A surfactant may be added to impart emulsifying properties, dispersibility, spreading properties, etc. during formulation.

When the herbicide composition of the present invention is used in the form of a wettable powder, it usually contains 5 to 55% by weight of the above-mentioned two compounds as active ingredients, 40 to 88% by weight of a solid carrier, and 2 to 5% of a surfactant.
A composition may be prepared by blending them in a proportion of 5% by weight, and this may be used.

When used in the form of an emulsion, the above two compounds are usually used as active ingredients in an amount of 10 to 50% by weight and a solvent as 35 to 7% by weight.
It may be prepared by mixing 5% by weight of the surfactant and 5-15% by weight of the surfactant.

On the other hand, when used in the form of a powder, it may be prepared by blending the above two compounds in a ratio of 1 to 20% by weight as active ingredients, 75 to 97% by weight of solid carrier, and 2 to 5% by weight of surfactant. .

Furthermore, when used in the form of granules, the above two compounds are used as active ingredients in an amount of 3 to 20% by weight and a solid carrier of 80 to 95% by weight.
It may be prepared by blending the surfactant in a proportion of 2 to 5% by weight.

Here, fine mineral powder is used as the solid carrier, and examples of the fine mineral powder include diatomaceous earth, oxides such as slaked lime, phosphates such as apatite, sulfates such as gypsum, talc, and pyroferite. Examples include silicates such as clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silica powder.

In addition, organic solvents are used as solvents, specifically aromatic hydrocarbons such as xylene, toluene, benzene, etc.
Chlorinated hydrocarbons such as chlorotoluene, trichloromethane, trichlorethylene, alcohols such as cyclohexanol, amyl alcohol, ethylene glycol, ketones such as inphorone, cyclohexanone, cyclohexenyl-cyclohexanone, butyl cellosolp, dimethyl ether, methyl ethyl ether, etc. Ethers, esters such as isoprobyl acetate, benzyl acetate, methyl phthalate,
Amides such as dimethylformamide or mixtures thereof can be mentioned.

Further, as the surfactant, any of anionic, nonionic, cationic, and amphoteric ionic types (amino acids, betaine, etc.) can be used.

The herbicidal composition of the present invention thus obtained has a high herbicidal effect not only on weeds in the early stage of growth, but also on weeds in a somewhat advanced stage of growth, and has a very wide range of suitable application periods.

In addition, there are many types of weeds that can be controlled, and it has been found to be extremely effective against not only annual weeds but also perennial weeds.

Moreover, a small amount of the drug is sufficient, and the effect is long-lasting.

Furthermore, the herbicidal composition of the present invention has no phytotoxic effects on crops such as paddy rice, and has very high utility value as a highly selective herbicide.

Therefore, when the herbicide composition of the present invention is applied to paddy field soil and field soil, it can exert excellent control effects on various weeds without causing chemical damage to paddy rice or various crops, and has an extremely excellent control effect. It can be widely and effectively used as a herbicide in various agricultural fields.

Next, examples of the present invention will be shown.

Example (1) Preparation of herbicide composition 97 parts by weight of talc (trade name: Zeeklite, manufactured by Zeeklite Chemical Industry Co., Ltd.) as a carrier, alkylaryl sulfonate (trade name: Neopellex) as a surfactant. 1.5 parts by weight of powder (registered trademark: manufactured by Kao Atlas Co., Ltd.) and surfactant (trade name: Solpol 800A (product name: Solpol 800A)
155 parts by weight of the product (registered trademark: manufactured by Toho Chemical Industry Co., Ltd.) were uniformly ground and mixed to obtain a wettable powder powder.

Next, various N-(α・α-dialkylbenzyl)phenylacetamide derivatives represented by the above structural formulas (I) to (V) obtained by the method in the synthesis example of JP-A-56-110655 were prepared. (Hereinafter referred to as "active ingredient A."

) or the known 3-(2,4-dichloro-5-impropoxyphenyl)5-t-butyl-1,3,4-oxadiazole-2(3H) monoone (hereinafter referred to as "active ingredient B")
That's what it means.

) and 90 parts by weight of the above-mentioned wettable powder carrier were uniformly ground and mixed to obtain a permanent powder.

Furthermore, predetermined amounts of the above-mentioned hydrating powder containing active ingredient A and aqueous phase agent containing active ingredient B diluted with water were mixed to prepare a herbicidal composition of the present invention.

(2) Biological test results ■ Flooded soil treatment test 1 Fill a 1/15500 are porcelain pot with paddy soil.
Novie seeds were uniformly sown on the surface layer, submerged in water to a depth of 3 cm, and grown in a greenhouse.

When the wildflowers reached the two-leaf stage, they were treated by uniformly spraying a predetermined amount of the herbicide composition obtained in (1) above on the water surface, and the plants were further grown in a greenhouse while being watered at appropriate times.

Thirty days after spraying the herbicide composition, the weight of the above-ground parts of the remaining wild grasses was measured, and the ratio to the untreated area was calculated.

The results are shown in Table 1.

In addition, the numerical values of the herbicidal effect in Table 1 are values calculated based on the following formula.

■ Flooded soil treatment test 2 A 1/400 are concrete pot placed outdoors was filled with gravel to a depth of 5 cm, on top of which was filled 2 cm of sand and 15 cm of paddy soil.

Next, add water until it is saturated, and add chemical fertilizer (product name:
Composite 8-8-8 (manufactured by Seiwa Fertilizer Industry Co., Ltd.) was used to cover 252 liters and seven 10 cm of surface layer per pot.

In addition to this, weeds, annual cyperus, annual broadleaf weeds,
Firefly seeds were uniformly sown, and two Mappai plants and five tubers each of Urikawa and Cyperus japonica were transplanted.

Furthermore, 8 paddy rice plants (Nihonbare, 2-leaf stage) were transplanted with 2 plants per plant, flooded with water to a depth of 3 cm, and 10 days after transplanting, the above (1
A predetermined amount of the herbicide composition obtained in ) was uniformly sprayed onto the water surface for treatment.

For 2 days from the day after the spraying treatment, insert a syringe needle into the rubber stopper of the drain and let the water leak at a rate of 3 cm/day.
The plants were grown by submerging them in water.

Thirty days after the spraying treatment, the above-ground fresh weight of the remaining weeds was measured for each grass species, and the ratio to the untreated plot was calculated.

In addition, the damage to paddy rice plants was observed by using hand-removed grass plots as a control.

The test was conducted in two series starting from the 1st day of May.

The results are shown in Table 2.

The numerical values of the herbicidal effect in Table 2 are values calculated based on the following formula.

In addition, the analysis results of compounds 1 to 5 in Table 1 are shown in Table 3.

In Table 3, infrared absorption spectra were conducted by the KBr tablet method, and proton nuclear magnetic resonance spectra were conducted by CDC.
1, as a solvent and TMS as an internal standard.

Claims (1)

[Scope of Claims] 1 N- selected from the group consisting of a compound represented by the structural formula, a compound represented by the structural formula, a compound represented by the structural formula, a compound represented by the structural formula, and a compound represented by the structural formula. (α・
α-Dialkylbenzyl) phenylacetamide derivative and 3-(2,4-dichloro-5-isopropoxyphenyl)5-t-butyl-1,3,4-oxadiazole-2(3H) monoone are active ingredients. A herbicide composition.