WO1998010654A1

WO1998010654A1 - Herbicidal compositions

Info

Publication number: WO1998010654A1
Application number: PCT/JP1997/003158
Authority: WO
Inventors: Shin-Ichiro Ogawa; Kazuyuki Takahashi
Original assignee: Idemitsu Kosan Co., Ltd.
Priority date: 1996-09-11
Filing date: 1997-09-08
Publication date: 1998-03-19
Also published as: JPH1087402A; AU4136397A

Abstract

Herbicidal compositions with which weeds over a wide range, in particular, broad-leaved weeds and grassy weeds can be effectively controlled at a low dosage without damaging crops such as wheat and turf. These compositions containing as the active ingredients (A) triazine derivatives represented by general formula (I) and/or salts thereof; and (B) isoxaben, wherein X1 represents C¿1-4? alkyl or halogeno; n is from 0 to 4; and R?1¿ represents C¿1-10? alkyl optionally having 1 to 4 substituents selected from among C1-4 alkoxy and hydroxy.

Description

Akira Itoda »Herbicide composition

Technical field

The present invention relates to a herbicidal composition, and more particularly, to a wide range of weeds, particularly broadleaf weeds and grasses, at low doses without causing phytotoxicity to crops such as wheat and lawns. Background art on herbicidal compositions that can be effectively controlled

To date, various herbicides have been developed, which has contributed to improving crop productivity and saving labor. However, the herbicides developed so far are not sufficiently wide in herbicidal spectrum, and the number of difficult-to-control weeds is increasing at present. Agents are needed. In addition, there is a need for a herbicide that has a small effect on the environment, a low dose and a high herbicidal effect.

The present inventors have proposed a triazine derivative represented by the following general formula (I) or a salt thereof (hereinafter, referred to as a triazine derivative (I)). It has been found that it is a compound that has high safety and a high herbicidal effect with a low dose, and has already filed a patent application (Japanese Patent Application No. 7-291, International Publication 9). 0-093778 publication).

The triazine derivative (I) has a high crop-to-weed selectivity, but there is a need for a herbicide that can control a wider range of weeds at a lower dose. Disclosure of the invention

The present invention is intended to effectively control a wide range of weeds, particularly broadleaf weeds and gramineous weeds, at a low dose without causing harm to crops such as wheat and lawns in such a situation. It is an object of the present invention to provide a herbicide composition that can contribute to further improving the productivity of agricultural crops and saving labor.

The present inventors have conducted intensive studies to achieve the above object, and as a result, when the triazine derivative (I) and isoxaben are used in combination, the synergistic action of these compounds achieves the object. The present inventors have found that the present invention has been completed based on this finding.

Therefore, the object of the present invention is to provide (A) —general formula (I)

(In the formula, X ¹ is a linear or branched alkyl group having 1 to 4 carbon atoms or a halogen atom, n is an integer of 0 to 4, and n is an integer of 2 or more. In this case, a plurality of X ¹ may be the same or different.

R ¹ is a linear or branched alkyl group having 1 to 10 carbon atoms, and the alkyl group is selected from an alkoxy group having 1 to 4 carbon atoms and a hydroquinol group. Or two or four identical or different groups. )

And (B) a triazine derivative represented by the following formula and / or a salt thereof:

This is achieved by a herbicide composition containing a compound represented by the formula (generic name isoxaben) as an active ingredient. BEST MODE FOR CARRYING OUT THE INVENTION

In the herbicidal composition of the present invention, the first active ingredient is represented by the general formula (I) which is the component (A):

The triazine derivative and Ζ or a salt thereof used in the above are used.

In the above general formula (I), X ′ represents a linear or branched alkyl group having 1 to 4 carbon atoms or a halogen atom.

Here, specific examples of the case where X ¹ is a linear or branched alkyl group having 1 to 4 carbon atoms include, for example, a methyl group, an ethyl group, and η-propyl Groups, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, cyclopropyl group, cyclobutyl group, and preferably a methyl group.

Specific examples when X ¹ is a halogen atom include, for example, a chlorine atom , A bromine atom, a fluorine atom and an iodine atom, and is preferably a fluorine atom.

X ¹ may be substituted at any of positions 2 to 6 of the benzene ring, preferably at position 3 and Z or 5.

In the above general formula (I), n represents an integer of 0 to 4, and is preferably

It is 0, 1 or 2, and particularly preferably 1 or 2.

Here, when n is an integer of 2 or more, a plurality of X ¹ may be the same or different.

In the above general formula (I), R ¹ is a linear or branched alkyl group having 1 to 10 carbon atoms, wherein the alkyl group is an alkoxy group having 1 to 4 carbon atoms and a hydroxyl group. It may be substituted by one group selected from the groups, or 2 to 4 same or different groups. Here, specific examples of R ′, which is not substituted by these groups, is a linear or branched alkyl group having 1 to 10 carbon atoms, are, for example, those described above. in addition to an alkyl group having 1 to 4 carbon atoms described in X ^1, n-pentyl, i-pentyl, sec-pentyl, tert - pentyl, Kishinore group to n, Kishinore group to i, sec - to Kishinore group, tert —hexynole, n-heptyl, i-heptyl, sec-heptyl, tert —heptyl, n-octyl., i-octyl, sec-octyl, tert-octyl , N nonyl group,

1-nonyl group, sec nonyl group, tert-nonyl group, n-decyl group, i-decyl group, sec-decyl group, tert-decyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc. And preferably methyl, ethyl, n-propyl, i-propyl, cyclopropyl, sec-butyl, tert-butyl, i-butyl, n-pentyl, and cyclohexyl. It is a lohexyl group. When R ¹ is an alkyl group having 1 to 10 carbon atoms substituted by an alkoxy group having 1 to 4 carbon atoms, specific examples of the alkoxy group having 1 to 4 carbon atoms as a substituent include: Examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, a tert-butoxy group, and the like. A tert-butyne group, particularly preferably a methoxy group.

When R ¹ is an alkyl group having 1 to 10 carbon atoms substituted with 2 to 4 groups selected from an alkoxy group having 1 to 4 carbon atoms and a hydroxy group, each substituent is They may be the same or different.

Specific examples of the case where R ′ is an alkyl group having 1 to 10 carbon atoms substituted by 1 to 4 groups selected from an alkoxy group having 1 to 4 carbon atoms and a hydroxy group. , for example, CH ₃ 0 CH - group, CH ₃ 0 CH ₄ - group, CH ₃ 0 CH - _{_{_{group, CH 3 0 C 4 H 8}}} - group, CH 0 CH one group, C ₂ H 0 CH, one group, C ₂ H _s 0 C ₃ H ₆ one _{_{group, C 2 H 0 C 4 H}} - group, C ₂ H ₅ OCH,. —Group, HO CH ₂ —Group, HO C ₂ H Group, H0 C ₃ H Group, HOC ₄ H ₈ —Group, (CHO) ₂ CH—Group, (CH ₃ O) ₂ C ₂ H ₃ Group , (CH ₃ 0 CH—group, (CH ₃ 0) CH 1 group, CH ₃ (0 CH) CH—group, C ₂ H ₅ (0 CH ₃ ) CH H_ group, CH ₃ OCH ₂ (CH ₃ ) 〇 11-2 group, (: ^ 1 ₃ 0 ((:} 1 ₃₎ ₂ {: - group, (CH ₃ 0) ₃ C-group, CH OH (CH) C-group, (CH ₃₎ C OH @ - Group, C ₂ H (OH) CH— group, cyclopropyl group substituted with methoxy group, cyclobutyl group substituted with methoxy group, cyclopentyl group substituted with methoxy group, methoxy group To a cyclohexyl group substituted with an ethoxy group, a cyclopentyl group substituted with an ethoxy group or a cyclohexyl group substituted with an ethoxy group. A xyl group and the like.

R ′ is preferably a straight-chain or branched C1-C4 group substituted by 1-4 groups selected from an alkoxy group and a hydroxy group each having 1-4 carbon atoms. 8 is an alkyl group. More preferably, it is a linear or branched alkyl group having 1 to 4 carbon atoms, which is substituted with 1 or 2 alkoxy groups having 1 to 4 carbon atoms, or 1 hydroxy group. It is a substituted linear or branched alkyl group having 1 to 4 carbon atoms. More preferably, R ¹ is a straight or branched C 1 -C 4 alkyl group substituted by one methoxy or one hydroxyl group .

The triazine derivative (I) has an optical isomer and is usually obtained as a racemate, but it is also possible to obtain only one of the enantiomers by a known method such as asymmetric synthesis. . The triazine derivative (I) of the present invention exhibits herbicidal activity whether it is a racemic form or an optical isomer alone. The triazine derivative (I) includes the above-mentioned racemic body and the above-mentioned optical isomers.

Further, the triazine derivative (I) can be used as a herbicidal active ingredient even if it is a salt of an inorganic acid or an organic acid.

Here, as an acid capable of forming a salt with the triazine derivative represented by the general formula (I), for example, hydrochloric acid, hydroiodic acid, hydrobromic acid, hydrofluoric acid And inorganic acids such as sulfuric acid, nitric acid and phosphoric acid; and organic acids such as sulfonic acid such as acetic acid, methanesulfonic acid and toluenesulfonic acid.

Specific examples of the triazine derivative (I) are shown in Tables 1 to 3 below. Table 1

Table 2

Table 3

] —

Le

The triazine derivative (I), which is the component (A) of the herbicidal composition of the present invention, is disclosed in Japanese Patent Application No. 7-291124 filed by the applicant of the present application and in International Publication No. It can be produced by the method disclosed in Japanese Patent Application Laid-Open No. 90-009378.

In other words, the reaction formula · ΗΧ ² of the following

One

(In the reaction formula, X ¹ , n and R ′ are as defined in the above general formula (I), X ² is a halogen atom, and R ² is an alkyl group having 1 to 4 carbon atoms. ) Can be produced by reacting an alkylbiguanide salt (1) with an ester (IV).

This reaction is preferably carried out in the presence of a catalyst. Examples of a catalyst that can be used in this reaction include sodium methoxide, sodium ethoxide, magnesium diethoxide, and the like. Alkoxides; inorganic bases such as sodium phosphate, potassium carbonate, sodium hydroxide and potassium hydroxide; and 1,8-diazabicyclo [5,4,0] — 7 — Dendene (DBU), 1, 5 — Diazabicyclo [4, 3, 0] — 5 — Organic bases such as nonane (DBN), triethylamine, pyridin, etc. Is And preferably sodium methoxide and sodium ethoxide.

The amount of the catalyst to be used is usually 1.1 to 10 equivalents, preferably 1.5 to 2 equivalents, relative to the salt of the alkyl biguanide (1 [1]).

The amount of the ester (IV) used in this reaction is usually 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to the alkyl biguanide salt (III). This reaction is preferably performed in the presence of a solvent. Examples of the solvent that can be used in the reaction include alcohols such as methanol, ethanol, and isopropanol; and acetate. , Methylethyl ketone, cyclohexanone, and other ketones; n-hexane, n-heptane, n-decane, and other aliphatic hydrocarbons; benzene, decalin, alkylnaphthalene Cyclic hydrocarbons such as carbon tetrachloride, methylene dichloride, cyclobenzene, dichlorobenzene, etc .; and ethers such as tetrahydrofuran and dioxane. Preferred are alcohols, and particularly preferred are methanol and ethanol.

In this reaction, a dehydrating agent can be used to prevent hydrolysis of the esters (IV). Examples of the water-removing agent that can be used in the method of the present invention include molecular sieve, anhydrous calcium sulfate, anhydrous sodium sulfate, sodium carbonate, calcium oxide, aluminum oxide, and aluminum oxide. Examples thereof include magnesium sulfate, potassium carbonate, and barium oxide, and molecular sieves and anhydrous calcium sulfate are particularly preferred. The amount of the dehydrating agent is from 10 to 200% by weight, preferably from 50 to 100% by weight, based on the salt of the alkyl biguanide (111).

The reaction temperature of this reaction is usually from 110 to 150 ° C, preferably from 110 to 120 ° C. The reaction time is usually 2 to 30 hours, but preferably about 10 to 15 hours.

I 1 After completion of the reaction, the reaction mixture is poured into water according to a conventional method, the desired product is extracted with an organic solvent such as ethyl acetate, and the obtained organic layer is dehydrated with a dehydrating agent such as anhydrous sodium sulfate. The organic solvent is removed by distillation under reduced pressure. By purifying the obtained residue by means such as silica gel column chromatography or the like, the desired triazine derivative (I) can be isolated as a crystal.

In the herbicidal composition of the present invention, as the second active ingredient, the formula (II), which is the component (B), is used.

Compound represented by: [Chemical name: N— [3— (1—ethyl-1—methyl pill) pill] isoxoxazolu-5—inole] 1,2,6—dimethoxybenzamide, generic name: isoxaben (Isoxaben)] is used. This isoxaben can be produced by a known method, and is also available as a commercial product.

The herbicidal composition of the present invention comprises a mixture of the triazine derivative (I) of the component (A) and the isoxaben of the component (B) (hereinafter, referred to as an active ingredient mixture) in a liquid such as a solvent. It can be mixed with a carrier or a solid carrier such as mineral fine powder and formulated into wettable powders, emulsions, powders, granules and the like. Further, the herbicidal composition of the present invention is obtained by mixing the above-mentioned components (A) and (B) with a liquid carrier or a solid carrier to form separate preparations, and then mixing the two preparations. May be manufactured. Formulation At this time, a surfactant may be added to impart emulsification, dispersibility, spreadability, and the like.

In the herbicidal composition of the present invention, the mixing ratio of the triazine derivative (I) of the component (A) and isoxaben of the component (B) depends on the type of crop, the type of weeds to be controlled, the climate, and the like. It should be determined appropriately depending on the conditions. The weight ratio is preferably 10: 1 to 1: 1100, more preferably 10: 1 to 1:10.

When the herbicidal composition of the present invention is used in the form of a wettable powder, it is usually 10 to 55% by weight of the active ingredient mixture, 40 to 88% by weight of the solid carrier and 2 to 5% by weight of the surfactant. The composition may be prepared by blending at a ratio of 1: 1.

When used in the form of an emulsion, it is usually prepared by mixing 20 to 50% by weight of the active ingredient mixture, 35 to 75% by weight of a solvent and 5 to 15% by weight of a surfactant. do it.

When used in powder form, it is usually prepared by mixing the active ingredient mixture at a ratio of 1 to 15% by weight, a solid carrier at 80 to 97% by weight and a surfactant at a ratio of 2 to 5% by weight. I just need.

In addition, when used in the form of granules, it is usually prepared by mixing 1 to 15% by weight of the active ingredient mixture, 80 to 97% by weight of the solid carrier, and 2 to 5% by weight of the surfactant. do it.

Here, a fine powder of a mineral substance is used as the solid carrier. Examples of the fine powder of the mineral substance include oxides such as silica earth and slaked lime, phosphates such as limestone, and phosphates. Examples thereof include sulfates such as copper, talc, pyrophyllite, cres, kaolin, bentonite, acid clay, white carbon, quartz powder, and gay salts such as gay stone powder.

In addition, an organic solvent is used as the solvent. Aromatic hydrocarbons such as luene and xylene, O—chloro chlorinated hydrocarbons such as toluene, trichloroethane and trichloroethylene, cyclohexanol, amyl alcohol, ethylene glycol Such as ketones such as alcohol, isophorone, cyclohexanone, cyclohexenone and cyclohexanone, ethers such as butyl ether, butyl ether, acetyl ether, and methyl ethyl ether; acetic acid Examples thereof include esters such as isopropyl, benzyl acetate and methyl phthalate, amides such as dimethylformamide and the like, and mixtures thereof.

As the surfactant, any of an anionic type, a nonionic type, a cationic type, and a zwitterionic type (amino acid, betaine, etc.) can be used.

Further, the herbicidal composition of the present invention can contain an insecticide, a fungicide, a plant growth regulator, a fertilizer, and the like, if necessary.

The herbicidal composition of the present invention is applied to a weed or a place where the weed grows, for example, before or after the germination of the weed.

The means of application varies depending on the cultivated plant and the environment of use, but may be, for example, spraying, watering, spraying, water injection and the like.

The herbicidal composition of the present invention is useful, for example, in cultivation of grasses such as rice, wheat, oats, maize, embark, sorghum, and broad-leaved crops such as soybean, peta, beet, beet, sunflower, and rape. It is also useful for vegetables such as fruit trees, fruits and vegetables, root vegetables and leafy vegetables, and lawns. The herbicidal composition according to the present invention may be, for example, a squirrel, a violet, a violet, a yamdara, a potato beetle, an odori koso, a hinagen, a wild sparrow, a wild sparrow, a wild sprout, Ichibi, Onomomi, Asagao, Shiroza, Aobu, Chosen Asagao, Inouhozuki, Enokorogusa, Meishishi, Oninogen, Seyoutapopo, Jyuta —It is useful for controlling weeds such as cane, nobu, konagi, kika sigsa, azena, mizohakobe, inu firefly, tamagayari, pine bye, mizugayaya, perica, omodaka, etc. Example

Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited to these examples.

<Reference Example 1> Production of Compound A-4 (triazine derivative (I)): 2- (3) synthesized using the method described in JP-A-63-264645 ', 5' — dimethyl pyroxy) Isopropylpyruguanide hydrochloride to 5.0 g (16.7 mmol) of sodium methoxide 28% by weight while stirring at room temperature Tanol solution 9.66 g (50.1 mm o

I) was added, and methylcyclopropylcarboxylate 5.01 (50. lmmol) was further added dropwise. After the reaction mixture was heated under reflux for 7 hours, the precipitate was separated by filtration and the filtrate was concentrated by an evaporator. To the obtained residue were added 50 mL of ethyl acetate and 50 mL of water, and the layers were separated. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off using an evaporator. The residue was purified by silica gel column chromatography (developing solvent).

: Hexane Z purified by ethyl acetate di-volume ratio 1 Z 1) L, the desired 2-amino 4-cyclopropyl 1 6-[2-(3,, 5 '-dimethylphenoxy) 1 1- [Methyleluamino] I, 1, 3, 5 — Triazine

(Compound A-4) 4.18 g (80% yield) was obtained.

<Reference Example 2> Production of compound A-5 (triazine derivative (I)): synthesized using the method described in Japanese Patent Application Laid-Open No. Sho 63-264645.

(3'-Fluorophenoxy) isopropylpyruguanide hydrochloride 5.00 g (19.9 mmo1) was added with sodium methoxide 28% by weight One to five g (59.7 mmol) of the no solution was added with stirring at room temperature. Further, 6.93 g (59.7 mmo 1) of methyl trimethyl acetate was added dropwise thereto. After the reaction solution was heated under reflux for 7 hours, the precipitate was separated by filtration and the filtrate was concentrated by evaporation. To the obtained residue were added 5 O ml of ethyl acetate and 50 ml of water, and the layers were separated. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl ester = volume ratio 1/1), and the desired 2—amino-4t-butyl-6— [2— (3 ′ [1, Fluorophenoxy) 1 -methyl-ethylamino] 1,1,3,5-triazine (Compound A-5) (4.77 g, yield 85%) was obtained.

Compounds A-1 to A-3 and A-6 to A-9 were produced according to Reference Examples 1 and 2.

Hereinafter, Formulation Examples of the herbicidal composition of the present invention are shown.

In Formulation Examples 1 to 4, Compounds A-1 to A-9 are the triazine derivatives shown in Tables 1 to 3, and Compound B is a compound represented by the formula (H). Chemical name: N— [3— (1—ethyl-1—methylpropyl) isosoxazole-1-5—yl] 1,2,6—Dimethoxybenzamide, generic name: isoxaben, trade name: tarzain (Dainippon) Ink Chemical Co., Ltd.)].

In the preparation examples, “parts” indicates “parts by weight”.

Formulation Example 1: wettable powder

Compound A-5 parts Compound B 5 parts Silicon earth 7 2 parts White carbon 1 5 parts Sodium alkyl benzenesulfonate 2 parts Sodium lignin sulfonate 1 part A wettable powder was prepared by uniformly mixing and grinding the above components. Formulation Example 2: Emulsion

Compound A-210 parts Compound B 10 parts Xylene 40 parts Dimethylformamide 20 parts Solpol 280 B (Toho Chemical Industry Co., Ltd.) 20 parts To uniformly dissolve and mix the above components Thus, an emulsion was prepared.

Formulation Example 3: Floatable

Compound A-210 parts Compound B 10 parts Methyl cellulose 0.5 parts Colloidal silica 1.5 parts Sodium ligninsulfonate 1 part Polyquineethylene nonylphenyl ether 2 parts Water 75 parts The above components were uniformly mixed and dispersed, and the obtained slurry-like mixture was wet-pulverized to prepare a flowable agent.

Formulation Example 4: Wettable powder

Cle as a carrier (trade name: G-Cryte, manufactured by G-Cryte Industries) 97 parts, Alkyl aryl sulfonate as a surfactant (trade name: Neovelex, manufactured by Kao Atlas Co., Ltd.) 1.5 parts, and a mixture of nonionic and anionic surfactants (trade name: Solpol 800A, Toho Chemical Industry Co., Ltd.) 1.5 parts were uniformly pulverized and mixed to obtain a carrier for wettable powder.

90 parts of this carrier for wettable powders and 10 parts of a triazine derivative (compounds A-1 to A-9) were uniformly ground and mixed to obtain wettable powders A-1 to A-9, respectively. Further, 90 parts of the above-mentioned wettable powder carrier and 10 parts of compound B (isoxaben) were uniformly ground and mixed to obtain wettable powder B.

The wettable powders A-1 to A-9 (hereinafter collectively referred to as wettable powder A) and wettable powder B obtained above correspond to the doses shown in Tables 4 and 7, respectively. By mixing at a weight ratio, a wettable powder as a herbicidal composition of the present invention containing Compounds A-1 to A-9 and Compound B in various combinations was obtained. <Example of weeding test>

Test example 1:

1/2 00 00 Field soil filled with field soil is filled with field soil, and seeds of oats, wheat and embak as crops, and yaemdara, oinu nofuguri and violet as weeds are sown. Then, after covering the soil, they were grown in a greenhouse.

The water-dispersible powder as the herbicidal composition of the present invention produced in Formulation Example 4 was suspended in water to prepare a herbicide suspension at each concentration. Spray was evenly sprayed over the entire surface of the pot at a liquid volume equivalent to 0 liter / hectare, so as to obtain the drug volume shown in Table 4 below.

After that, the plants were grown in a greenhouse, and after the treatment, the herbicidal and herbicidal effects on crops were judged according to the following criteria. The results are shown in Table 4 below. Crop damage

0 not recognized

1 Almost no 2 Somewhat acceptable

3 Accepted

4 Notable

5 Almost dead Herbicidal effect Herbicidal rate ()

0 Less than 5%

15% or more and less than 20%

220% or more and less than 40%

340% or more and less than 70%

4 70% or more and less than 90%

590% or more The herbicidal rate was calculated from the following formula by measuring the fresh amount of the above-ground weeds. Herbicidal rate (%)-(1 fresh amount in one treatment area Z fresh amount in non-treatment area) X100 For comparison, the above-mentioned composition was used instead of the wettable powder as the herbicide composition of the present invention. The phytotoxicity and herbicidal effect were examined by the same evaluation method as above, except that each of the wettable powder A and the wettable powder B prepared in Formulation Example 4 were used alone. The results are shown in Table 5 below. Table 4 Triazine derivatives Compound B Herbicidal effect

Active ingredient medicine heat effective dosage amount

(g / ha) Ingredient (g / ha)

A— 1 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A—? 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0 ∑ Δ — Q R D? N Ω 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A— 4 R 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A-5 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A-6 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A-7 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A-8 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

A-9 1 0 0 B 2 0 0 5 5 5 0 0 0

5 0 1 0 0 5 5 5 0 0 0

Herbicidal effect Pharmaceutical damage Active ingredient Prescription amount

\ 6 / lid no gura nofuguri

A-1 1 0 0 2 5 5 0 0 0

1 3 4 0 0 0

! A-2 1 0 0 3 5 5 0 0 0

J u 2 4 0 0

table

U A-3 1 0 0 3 5 4 0 0 0 Re J u 1 3 0 0

^{3 Three} ⁰⁰

A

A—4 1 0 0 3 4 4 0 0 0

D U 1 2 3 0 0

⁰⁰

Induction A-5 1 0 0 2 5 0 0 0 0 Body J u 2 3 0 0

^4Four

A-6 1 0 0 3 5 5 0 0 0

5 0 2 4 4 0 0

A-7 1 0 0 3 5 4 0 0 0

5 0 1 3 4 0 0 0

A-8 1 0 0 2 4 4 0 0 0

5 0 1 3 2 0 0 0

― One

A-9 1 0 0 2 4 4 0 0

5 0 1 4 2 0 ° o 0 Compound B 2 0 0 2 3 3 0

1 0 0 2 3 2 0 ⁰ ⁰ Based on the results in Tables 4 and 5, the herbicidal composition of the present invention comprising the wettable powder A and the wettable powder B is effective against any of the weeds Yaemudara, Ooi Nunofuguri and Violet. It shows excellent herbicidal effect and does not cause phytotoxicity to wheat, wheat, and endemic plants.However, when wettable powder A and hydrated powder B are applied independently, the herbicidal effect depends on the type of weed. In some cases, sufficient herbicidal effects could not be obtained.

Test example 2:

In order to evaluate the synergistic effect of the herbicidal composition of the present invention, the following formula was used based on the herbicidal rate against yamgra when wettable powder A and wettable powder B measured individually in Test Example 1 were individually treated. The predicted value (QE) was calculated based on the above, and compared with the herbicidal rate (actually measured value) against yamgra when the wettable powder was applied as the herbicide composition of the present invention measured in Test Example 1 above. If the measured value exceeds the predicted value, it is determined that there is a synergistic effect.

Q E = Q a + Q b-(Q a · Q b / 100) Q E: Predicted value

Qa: Actual value of the herbicidal rate when only Compounds A—1 to A-9 are used as active ingredients in a quantity equivalent to hectares of a gram.

Qb: Measured value of the herbicidal rate when compound B alone is applied as an active ingredient in an amount equivalent to b gram Z hectare. The results are shown in Table 6 below. Table 6

* Δ: Actual measured value of herbicidal rate-Predicted value of herbicidal rate From the results in Table 6, the (Α) component (compound A-11 to A-9) and the (B) component (compound B) of the herbicidal composition of the present invention are shown. The synergistic effect of herbicidal effect in combination with) is evident in the case of Yaemdara. That is, in all of the herbicidal compositions of the present invention, the difference (Δ) between the measured value and the predicted value of the herbicidal rate against Yamgra was 37 to 44%, and it was clear that a high synergistic effect was exhibited. became. .

Test example 3:

1 Z 200 Filled with field soil Put the field soil in the Arr. Seeds of Shiva, Oninogeshi and S. dandelion were sown and grown in a greenhouse after covering the soil.

The wettable powder as the herbicidal composition of the present invention produced in Formulation Example 4 was mixed with water. To prepare a herbicide suspension of each concentration, and after 3 days from the seeding, prepare a herbicide suspension in a volume equivalent to 500 liter hectares, each with the amount shown in Table 8 below. It was sprayed evenly over the entire surface of the pot.

Thereafter, the plants were grown in a greenhouse, and on day 30 after the treatment, the phytotoxicity to the lawn and the herbicidal effect were determined based on the same criteria as in Test Example 1. However, in Test Example 1, it was crop damage, but in this example, it was lawn damage. The results are shown in Table 7 below.

For comparison, the same as the above except that the wettable powder A and the wettable powder B prepared in Formulation Example 4 were used alone instead of the wettable powder as the herbicidal composition of the present invention. The phytotoxicity and herbicidal effect were examined by the evaluation method. The results are shown in Table 8 below.

Table 7

Table 8

From the results in Tables 7 and 8, the herbicidal composition of the present invention obtained by mixing the wettable powder A and the wettable powder B shows that the herbicidal composition of the present invention is as follows: It shows herbicidal effects against all the weeds of Campanella, especially shows excellent herbicidal effects against Oninogeshi and Saitama-no-mpopo, and does not cause phytotoxicity to Copa maize and Noshiba. On the other hand, when the wettable powder B was applied alone, the herbicidal effect on Ononi-gesoshi and Acacia catechu was considerably inferior to that of the herbicidal composition of the present invention.

Test example 4:

In order to evaluate the synergistic effect of each component of the herbicidal composition of the present invention, from the herbicidal rate against Oninogeshi when wettable powder A and wettable powder B measured alone in Test Example 3 were each treated alone, The predicted value (QE) was calculated in the same manner as in Test Example 2, and the herbicidal rate against Oninogeshi was determined when the wettable powder as the herbicidal composition of the present invention measured in Test Example 3 was applied. (Measured value). If the measured value exceeds the predicted value, it is determined that there is a synergistic effect. The results are shown in Table 9 below.

Table 9

* Δ: Actual measured value of herbicidal rate-Predicted value of herbicidal rate Based on the results in Table 9, the components (A) (compounds A11 to A-9) and (B) (compound B) of the herbicidal composition of the present invention are shown The synergistic synergistic effect of herbicidal effects in combination with is clear from the example of ononogen. That is, in all the herbicidal compositions of the present invention, the difference (Δ) between the actually measured value and the predicted value of the herbicidal rate against P. aeruginosa was 1 to 13%, and it was clear that a good synergistic effect was exhibited. Was. Industrial applicability

INDUSTRIAL APPLICABILITY The herbicidal composition of the present invention can effectively control a wide range of weeds, particularly broadleaf weeds and gramineous weeds, at low doses without causing harm to crops such as wheat and lawns. This can contribute to further improving the productivity of agricultural crops and saving labor.

Claims

The scope of the claims

(A) General formula (I)

(Wherein, X ′ is a linear or branched alkyl group having 1 to 4 carbon atoms or a halogen atom, n is an integer of 0 to 4, and n is an integer of 2 or more. In the case, multiple X's may be the same or different from each other

And one or more members selected from the group consisting of triazine derivatives and salts thereof, represented by the formula (B):

A herbicidal composition comprising a compound represented by the formula (generic name isoxaben) as an active ingredient.

2. The herbicidal composition according to claim 1, wherein X 'in the general formula (I) is a methyl group or a fluorine atom.

3. The herbicidal composition according to claim 2, wherein n is 1 or 2 in the general formula (I).

4. The herbicidal composition according to claim 3, wherein the substitution position of X 'in the general formula (I) is selected from the group consisting of the 3-position and the 5-position of the phenyl group.

5. The herbicidal composition according to any one of claims 1 to 4, comprising the component (A) and the component (B) in a weight ratio of 10: 1 to 1: 1100.