JPH11349411A - Controlling agent for weed and controlling - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a controlling agent for weeds resistant to sulfonylurea-based herbicides having high herbicidal effects and high safety for paddy rice by including at least one kind of a (dichloro-tolyloxy)propionanilide and an N- phenyl-(naphthyloxy)propionanilide. SOLUTION: This controlling agent for weeds is obtained by including at least one of (A) preferably 0.01-80 pts.wt. of (RS)-2-(2,4-dichloro-m-tolyloxy) propionanilide represented by formula I and (B) preferably 0.01-80 pts.wt. of N-phenyl-2-(2-naphthyloxy)propionanilide represented by formula II as an active ingredient. The controlling agent can be prepared as a granule, an emulsion, a wettable powder, etc., by mixing the active ingredient with a solid or a liquid carrier, a diluent, a surfactant, etc. The optimal amount of the applied controlling agent is preferably 0.1-100 kg per hectare based on the total amount of the active ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a herbicide for paddy fields, and more particularly, it is extremely safe for paddy rice when applied before, during or after transplantation of paddy rice.
The present invention relates to a paddy field herbicide and a herbicidal method showing a high herbicidal effect on a sulfonylurea herbicide-resistant weed.

[0002]

2. Description of the Related Art Many herbicides have been put to practical use for paddy fields, and they have been widely and generally used as a single agent or a mixture containing two or more active ingredients.
In particular, the mainstream is various admixtures containing various gramineous weed controlling agents effective for gramineous weeds and sulfonylurea herbicides effective for annual broadleaf weeds and perennial weeds. However, in recent years, the emergence of weeds having resistance to sulfonylurea herbicides has been observed, and its control has become a problem.

The compound (1) used as an active ingredient of the weed controlling agent of the present invention is disclosed in Japanese Patent Application Laid-Open No. 57-171904.
And a known herbicide described in (1), Compound (2)
Is a known herbicide described in JP-A-51-38419. However, Japanese Patent Publication No. Sho 5
No. 7-171904 or JP-A-51-384.
No. 19 does not disclose that compound (1) or compound (2) exhibits a high herbicidal effect on sulfonylurea-based herbicide-resistant weeds.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a weed controlling agent and a method for controlling weeds which have a high herbicidal effect against sulfonylurea herbicide-resistant weeds and have high safety against rice.

[0005]

Means for Solving the Problems The present inventors have conducted various studies in order to develop a herbicide for paddy fields that meets the needs of the above-mentioned agricultural workers. As a result, unexpectedly, it was found that the compound (1) and the compound (2) have a high herbicidal effect on sulfonylurea-based herbicide-resistant weeds, and the sulfonylurea-based herbicide-resistant weed-controlling agent of the present invention and The control method has been completed.

That is, the present invention provides the following formula (1)

[0007]

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(RS) -2- (2,4-dichloro-m-tolyloxy) propionanilide (general name: clomeprop, described in JP-A-57-171904) represented by the following formula: 2)

[0009]

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Wherein at least one of N-phenyl-2- (2-naphthyloxy) propionanilide (generic name: naproanilide, described in JP-A-51-38419) represented by the following formula is contained as an active ingredient: Application of a pesticide formulation characterized by containing as an active ingredient the above-mentioned herbicide active substance, which is effective against sulfonylurea-based herbicide-resistant weeds and sulfonylurea-based herbicide-resistant weeds, to flooded sewage paddy fields It is intended to provide a method for controlling weeds resistant to sulfonylurea-type herbicides, characterized by performing the following.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The compound (1) used as an active ingredient of the weed controlling agent of the present invention is disclosed in Japanese Patent Application Laid-Open No. 57-17 / 1982.
No. 1904, and the compound (2) is a known herbicide described in JP-A-51-38419.

In the weed controlling agent of the present invention, the compound (1)
When the compound (1) and the compound (2) are used in combination, the content ratio of the compound (1) and the compound (2) is not strictly limited, and depends on the application area of the final weed control agent, the applicable weeds, the application time, and the like. Although it can be varied over a wide range, in general, 0.001 of compound (1) per weed control agent of the present invention is used.
1 to 99 parts by weight, preferably 0.01 to 80 parts by weight, 0.001 to 99 parts by weight of compound (2), preferably 0.01 to
It is appropriate to mix or mix in a proportion of up to 80 parts by weight.

When the weed controlling agent of the present invention is actually used as a herbicide, the above active ingredient is mixed with a known solid or liquid carrier or diluent, surfactant or other auxiliary agent for formulation to form a pesticide. Can be prepared in the usual pharmaceutical forms used as, for example, granules, emulsions, wettable powders, flowables, dry flowables, jumbo and the like.

As the solid carrier which can be used in the production of the weed controlling agent of the present invention, clays represented by kaolinite group, montmorillonite group, illite group or polyglossite group, more specifically, pyrophyllite, attapulgite, sepiolite, kaoli Knight, bentonite,
Inorganic substances such as saponite, vermiculite, mica and talc, and gypsum, calcium carbonate, dolomite, diatomaceous earth, calcite, magnesium lime, apatite, zeolite, silicic anhydride, synthetic calcium silicate;
Plant organic substances such as tobacco flour, walnut flour, wheat flour, wood flour, starch, and crystalline cellulose; such as coumarone resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, copal gum, and dammal gum Synthetic or natural polymer compounds;
Examples include waxes such as carnauba wax and beeswax, and urea.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as xylene, ethylbenzene, cumene and methylnaphthalene; trichloroethylene, monochlorobenzene Chlorinated hydrocarbons such as o-chlorotoluene; ethers such as dioxane and tetrahydrofuran; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone and isophorone; ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, and maleic Esters such as dibutyl acrylate and diethyl succinate; n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol,
Alcohols such as benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethyl sulfoxide; and water.

In addition, emulsification, dispersion, and wetting of the active ingredient
Surfactants, fixing agents and other auxiliaries can be used for the purpose of spreading, fixing, binding, controlling disintegration, stabilizing the active ingredient, improving fluidity, preventing rust, and the like. As examples of surfactants used, any of non-ionic, anionic, cationic and zwitterionic compounds can be used, but usually non-ionic and / or anionic Compounds are used. Suitable nonionic surfactants include, for example, compounds obtained by polymerizing ethylene oxide with higher alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol; compounds obtained by polymerizing ethylene oxide with alkylphenols such as isooctylphenol and nonylphenol; butyl Compounds obtained by polymerization addition of ethylene oxide to alkyl naphthols such as naphthol and octyl naphthol; palmitic acid,
Compounds obtained by polymerizing ethylene oxide with higher fatty acids such as stearic acid and oleic acid; Compounds obtained by polymerizing ethylene oxide with amines such as dodecylamine and stearic acid; higher fatty acid esters of polyhydric alcohols such as sorbitan and ethylene oxide Compounds obtained by polymerization addition; compounds obtained by block polymerization addition of ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, alkyl sulfates such as sodium lauryl sulfate and amine salt of oleic alcohol sulfate; alkyl sulfonates such as sodium dioctyl sulfosuccinate and sodium 2-ethylhexene sulfonate; And arylsulfonic acid salts such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate and sodium dodecylbenzenesulfonate. Furthermore, the composition of the present invention improves the performance of the preparation, and for the purpose of enhancing the herbicidal effect, casein, gelatin, albumin, glue, lignin sulfonate, alginate, acacia, xanthan gum, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose , Polyvinyl alcohol, polyvinylpyrrolidone, polysaccharides and other high molecular compounds and other auxiliaries can also be used in combination.

The above-mentioned carriers and various auxiliaries can be used singly or in combination depending on the purpose, taking into account the dosage form of the preparation, the application scene, and the like.

The content of the active ingredient in the composition of the present invention in the various preparations thus obtained varies depending on the preparation, and is, for example, 0.01 to 99% by weight, preferably 0.1 to 100% by weight. ~ 80% by weight.

In the case of wettable powders, for example, the active ingredient is usually 1
To 90% by weight, with the balance being a solid carrier and a dispersing wetting agent to which a protective colloid agent, an antifoaming agent and the like are added if necessary.

In the case of granules, for example, the active ingredient is usually contained in 0.1 mg.
The content is from 01 to 35% by weight, and the balance is a solid carrier and / or a surfactant. The active ingredient is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the diameter of the particles is about 0.05 to 3.0 m.
m, preferably about 0.2-1.5 mm.

In the case of a flowable, for example, the active ingredient is usually contained in an amount of 0.5 to 50% by weight, and 3 to 10% by weight.
% By weight of a dispersing wetting agent, the balance being water, and if necessary, protective colloids, preservatives, defoamers, antifreezing agents and the like are added.

The appropriate application amount of the weed controlling agent of the present invention prepared as described above depends on weather conditions, soil conditions, formulation of the weed controlling agent, target crop, target weed, application time, application method and the like. However, it is usually 0.01 to 100 per hectare based on the total amount of the active ingredients.
A range of 0 kg, preferably 0.1-100 kg is suitable. Further, the weed control agent of the present invention can be made into a labor-saving control agent by appropriately mixing other herbicides, insecticides, fungicides, plant growth regulators and the like.

Further, if necessary, it can be mixed with other various insecticides, fungicides, plant growth regulators, herbicides and other drugs or fertilizers when spraying.

Hereinafter, the present invention will be described specifically with reference to examples.

[0025]

Example 1 (Floable agent) Compound (1) 10.0% by weight Polyoxyethylene nonylphenyl ether 2.0% by weight Sodium dioctylsulfosuccinate 2.0% by weight Xanthan gum 0.2% by weight Water 85.8 The weight% or more was wet-pulverized by a wet ball mill to obtain a flowable agent.

Example 2 (Granules) Compound (1) 10.0% by weight Sodium ligninsulfonate 3.0% by weight Sodium alkylnaphthalenesulfonate 1.0% by weight Bentonite 30.0% by weight Talc 56.0% by weight After mixing and grinding the above, the mixture was granulated by a usual method using a granulator and dried to obtain granules.

Example 3 (Wettable powder) Compound (1) 10.0% by weight Sodium ligninsulfonate 3.0% by weight Sodium dialkylnaphthalenesulfonate 3.0% by weight Kaolin 84.0% by weight To obtain a wettable powder.

Example 4 (Floable agent) Compound (2) 10.0% by weight Polyoxyethylene nonyl phenyl ether 2.0% by weight Sodium dioctyl sulfosuccinate 2.0% by weight Xanthan gum 0.2% by weight Water 85.8% by weight % Or more was wet-pulverized with a wet ball mill to obtain a flowable agent.

Example 5 (Granules) Compound (2) 10.0% by weight Sodium ligninsulfonate 3.0% by weight Sodium alkylnaphthalenesulfonate 1.0% by weight Bentonite 30.0% by weight Talc 56.0% by weight After mixing and grinding the above, the mixture was granulated by a usual method using a granulator and dried to obtain granules.

Example 6 (Wettable powder) Compound (2) 10.0% by weight Sodium ligninsulfonate 3.0% by weight Sodium dialkylnaphthalenesulfonate 3.0% by weight Kaolin 84.0% by weight To obtain a wettable powder.

Example 7 (Floable agent) Compound (1) 1.5% by weight Compound (2) 7.5% by weight Polyoxyethylene nonylphenyl ether 2.0% by weight Sodium dioctylsulfosuccinate 2.0% by weight Xanthan gum 0 Water of 86.8% by weight or more was wet-ground with a wet ball mill to obtain a flowable agent.

Example 8 (Granules) Compound (1) 1.5% by weight Compound (2) 7.5% by weight Sodium ligninsulfonate 3.0% by weight Sodium alkylnaphthalenesulfonate 1.0% by weight Bentonite 30. After mixing and pulverizing 0% by weight of talc 57.0% by weight or more, the mixture was granulated by a usual method using a granulator and dried to obtain granules.

Example 9 (Wettable powder) Compound (1) 1.5% by weight Compound (2) 7.5% by weight Sodium ligninsulfonate 3.0% by weight Sodium dialkylnaphthalenesulfonate 3.0% by weight Kaolin 85 0.0 wt% or more was mixed and pulverized to obtain a uniform wettable powder.

As Comparative Example 1, a known sulfonylurea-based herbicide, bensulfuron-methyl (JP-A-57-1)
12379) as a 10% wettable powder. As Comparative Example 2, a known sulfonylurea herbicide, pyrazosulfuron-ethyl (Japanese Patent Application Laid-Open No.
Commercially available Sirius granules containing 0.07% (described in No. 122488) were used. Sirius is a registered trademark of Nissan Chemical Industries, Ltd.

The mechanism of action of these known herbicides is all said to be acetolactate biosynthesis enzyme inhibition.

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

Test Example 1 (Herbicidal Effect on Sulfonylurea Herbicide-Resistant Weeds and Damage to Paddy Rice by Soil Treatment before Transplantation) Paddy soil and chemical fertilizer were put in a concrete pot of 0.25 m ² , and an appropriate amount of water was added. And mix well to make the paddy field, and the sulfonylurea-based herbicide-sensitive Mizuoi (Monochoria korsakowii), the sulfonylurea-based herbicide-resistant Mizuoi (Monoc)
horia korsakowii), a sulfonylurea herbicide-sensitive firefly (Sirpus junc)
oidees), sulfonylurea herbicide-resistant firefly (Sirpus juncoides) and sulfonylurea herbicide-resistant bamboo azaena (Linde)
rnia dubia var. dubia Pen
(nell) seeds were sown in fixed amounts. One day after sowing of the weeds, a predetermined amount of the test compound was treated using the preparations prepared according to Examples 1 to 9. Four days after the chemical treatment, two 2-leaf paddy rice seedlings that had been grown in a greenhouse in advance were transplanted as 6 plants per pot.

Table 2 shows the results obtained by examining the herbicidal effect and the degree of phytotoxicity of paddy rice 30 days after the chemical treatment.

The herbicidal effect and the degree of rice phytotoxicity for each herb species in the table are evaluated in six grades from "0" to "5", respectively, as shown in Table 1 below. It is represented by a six-step code from "-" to "++++".

Test Example 2 (Herbicidal Effect on Sulfonylurea Herbicide-Resistant Weeds and Damage to Paddy Rice by Soil Treatment after Transplantation) Paddy soil and chemical fertilizer were put in a concrete pot having an area of 0.25 m ² , and an appropriate amount of water was added. And mix well to make the paddy field, and the sulfonylurea-based herbicide-sensitive Mizuoi (Monochoria korsakowii), the sulfonylurea-based herbicide-resistant Mizuoi (Monoc)
horia korsakowii), a sulfonylurea herbicide-sensitive firefly (Sirpus junc)
oidees), sulfonylurea herbicide-resistant firefly (Sirpus juncoides) and sulfonylurea herbicide-resistant bamboo azaena (Linde)
rnia dubia var. dubia Pen
(nell) seeds were sown in fixed amounts. Five days after sowing of the weeds, two 2-leaf paddy rice seedlings previously grown in a greenhouse
Six strains were transplanted per pot as strains.

On the day of transplantation (after transplantation), a predetermined amount of the test compound was treated with a preparation prepared according to Examples 1 to 9.

Table 3 shows the results obtained by examining the herbicidal effect and the degree of chemical damage to rice 30 days after the chemical treatment.

In addition, the herbicidal effect and the degree of rice phytotoxicity for each grass species in the table are evaluated on a six-point scale from "0" to "5", respectively, as shown in Table 1 below. It is represented by a six-step code from "-" to "++++".

Test Example 3 (Herbicidal Effect on Sulfonylurea Herbicide-Resistant Weeds and Chemical Damage to Paddy Rice by Foliage and Soil Treatment) A test pot was prepared in the same manner as in Test Example 2, and 15 days after transplantation, a test compound was prepared. A predetermined amount was treated with a preparation prepared according to Examples 1 to 9.

Table 4 shows the results obtained by examining the herbicidal effect and the degree of chemical damage to rice 30 days after the chemical treatment.

The herbicidal effect and the degree of rice phytotoxicity for each herb species in the table are evaluated on a six-point scale from "0" to "5", respectively, as shown in Table 1 below. It is represented by a six-step code from "-" to "++++".

[0047]

[Table 1]

[0048]

[Table 2]

[0049]

[Table 3]

[0050]

[Table 4]

[0051]

From the results of the above test examples, it can be seen that the weed controlling agent of the present invention has a high herbicidal effect on sulfonylurea herbicide-resistant weeds.

That is, when a sulfonylurea herbicide was applied at twice the dose of a commonly used drug, it did not show a sufficient herbicidal effect on weeds resistant to the herbicide. The weed controlling agent of the present invention is, as apparent from the above test examples, soil treatment before transplantation, soil treatment after transplantation and foliage and soil treatment, in any dosage form of granules, flowables and wettable powders, The sulfonylurea herbicide showed a high herbicidal effect on resistant weeds showing no herbicidal effect at all, and no or almost no phytotoxicity was observed on rice.

The period of use can be arbitrarily selected from a wide range from before rice transplantation to the weed growth period (about 20 days after transplantation). The highest herbicidal effect can be obtained if the treatment is carried out until about 15 days.

The above results clearly show that compound (1), compound (2), and a mixture of compound (1) and compound (2) have a high herbicidal effect against sulfonylurea-based herbicide-resistant weeds. It shows. Therefore, the present invention can provide a herbicide and a herbicidal method having a higher herbicidal effect on a sulfonylurea-based herbicide-resistant weed, and is a very useful agricultural technique.

Claims (2)

[Claims] [Claim 1] The following formula (1) (RS) -2- (2,4-dichloro-m-tolyloxy) propionanilide represented by the following formula (2): N-phenyl-2- (2-naphthyloxy) represented by
A sulfonylurea herbicide-resistant weed control agent comprising at least one propionanilide as an active ingredient. 2. A pesticide preparation comprising the herbicidal drug substance according to claim 1 as an active ingredient, which is effective against sulfonylurea herbicide-resistant weeds. A method for controlling weeds resistant to sulfonylurea herbicides.