WO1994004511A1

WO1994004511A1 - Pyrimidine derivative and weedkiller

Info

Publication number: WO1994004511A1
Application number: PCT/JP1992/001057
Authority: WO
Inventors: Yasuo Kawamura; Jun Satow; Kenzou Fukuda; Kaoru Itoh; Hiroshi Kita; Tsutomu Nawamaki; Shigeomi Watanabe; Kimihiro Ishikawa
Original assignee: Nissan Chemical Industries, Ltd.
Priority date: 1992-08-21
Filing date: 1992-08-21
Publication date: 1994-03-03
Also published as: AU2448292A

Abstract

A uracil derivative represented by general formula (I), a weedkiller containing the same, and a method for killing weeds and inhibiting the growth thereof by applying the same, wherein R1 represents NR6R7 (wherein R?6 and R7¿ represent each independently hydrogen or C¿1? to C4 alkyl) or OR?8¿ (wherein R8 represents hydrogen or C¿1? to C4 alkyl); R?2¿ represents C¿1? to C6 alkyl or trifluoromethyl; R?4¿ represents hydrogen or halogen; R5 represents halogen or nitro; and D26 represents C¿1? to C4 alkyl or C1 to C3 haloalkyl.

Description

Specification

Pyrimidine derivatives and herbicides

The present invention relates to a novel peracil derivative and a selective herbicide containing the derivative as an active ingredient. Background art

It has been known that certain compounds of peracyl derivatives exhibit herbicidal activity. For example, The Pesticide Manual, 8th edition, page 89, The 'Pretish' crop Bromacil is described as one of the herbicides having a peracil skeleton in the 'Protection' Council (The British Crop Protection Council) (1987).

Furthermore, JP-A-61-221178 (= U.S. Patent No. 4,746,352, U.S. Patent No. 4,760,163), JP-A-63-41466 (= U.S. Patent No. 4,859,229), JP-A-63-107967 (= U.S. Patent No. 4,812,164), JP-A-54-147923 (= U.S. Patent No. 4, 266, 056, U.S. Patent No.

U.S. Pat.No. 4,927,451, U.S. Pat.No. 4,941,909,

Peracyl derivatives are disclosed in EP 0 408 382 A2, EP 0 489 480 A1 and the like. Disclosure of the invention

Equation (I):

N-S0 ₂ -D 26 (I) [In the formula, R ¹ is NR ^S R ⁷ (R ⁶ and R ⁷ each independently represent a hydrogen atom or a C ₄ alkyl group.) Or OR ⁸ (R ⁸ represents a hydrogen atom or a d- ₄ alkyl group. R ² represents a ₆ alkyl group or a trifluoromethyl group, R ⁴ represents a hydrogen atom or a halogen atom, R ⁵ represents a halogen atom or a nitro group, D ²⁶ represents an alkyl group, C represents a ₃ haloalkyl group. ]

And a selective herbicide containing the derivative as an active ingredient.

Structural features of the present invention compounds have an NR ⁶ R ⁷ or OR ⁸ in 1-position of Urashiru ring, and R ⁴ as 3-position benzene ring substituents of Urashiru ring, R ⁵ and NHS 〇 ₂ D ^{It has 26} unique combinations.

Next, the substituent of the formula (I) will be specifically described.

R ¹ is an amino group, a methylamino group, an ethylamino group, an n-propylamino group, an iso-propylamino group, a tert-butylamino group, a dimethylamino group, a hydroxyl group, a methoxy group, an ethoxy group, or n- Examples include a propoxy group, an iso-propoxy group and an n-butoxy group, and preferably an amino group.

R ² represents trifluoromethyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl , Neo-pentyl and n-hexyl, and the like, preferably trifluoromethyl, methyl, ethyl, n-propyl and iso-propyl.

Hydrogen atom as R ^4, a fluorine atom, a chlorine atom, is mentioned, et al is a bromine atom and an iodine atom, preferably a hydrogen atom, fluorine atom and chlorine atom.

Nitro group as R ^5, a fluorine atom, a chlorine atom, is mentioned, et al is a bromine atom and an iodine atom, preferably a chlorine atom and a bromine atom.

Methyl group as D ^26, Echiru group, n- propyl group, iso- flop π propyl group, _n - Bed methyl group, halogenated methyl, halogenated modified chill, halogenated n- propyl and c Isogenated isopropyl, etc. Halogen here represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Tables 1 and 2 show specific examples of the compound of the present invention, but the present invention is not limited by these.

-i-

(Table 1)

Turbulent NH ₂

CH ₃

NH ₂ NH ₂

CH3CH2CH2

H

-S0 ₂

R ⁵

NH ₂ NH ₂ ₂ -D ²⁶

2-D ²⁶

NH:

Or CF ₃ people 0

N-SO2-D ²⁶

[Table 1 (continued)]

RRD 26

F C1 CH (CH ₃ ) ₂ F C1 Π2θΗ2 rl2Cfl3 F C1 CH (CH ₃ ) CH ₂ CH ₃ F C1 CH ₂ CH (CH ₃ ) ₂ F C1 C (CH ₃ ) ₃

FF CH ₃

FF CH (CH ₃ ) ₂

FF CH (CH ₃ ) CH ₂ CH ₃ FF CH2CHCCH3) 2 FFC (CH ₃ ) ₃ FF CH ₂ CF ₃

HF CH ₃

HF CH2CH2CH3

D

^ 0 ^ 06 / drh> d0 / z60 Sl

) 3 HH. The same

Q H. "

CD CD CD CD CD

c CO CO CO ca ca ca OQ OQ αα CQ OQ DQ z z z

§H. in PC pi: ¾ ^: CJ)> J> CJ -5 J> tJ ^ Cl-

) Ή. Η.

3H3 "H."

). H.

H. [Table 1 (continued) :)

R R D 2 6

F NO 2 CH (CH ₃ ) CH ₂ CH ₃

F NO 2 C (CH ₃ ) ₃ F NO ₂ CH ₂ CF ₃

F NO 2 CH2CH2CH2CI

^ε Η3 ^ζ Η3 ³ ( ^ε Η3) Η00

εΗ3 ^ζ ( ^ε Η3) Η30

εΗ3 ^ζ Η3 ^ε Η3 ^ζ Η30

^εΗ3 ζ Η30

εΗ3 ^Σ Η3 ^ε ΗΟΟ

3 ^ε Η30

ΗΟ

εΗ3 ΗΟ

εΗ0 ^ζ Η3 ^Σ ( ^ε Η3) Ν

εΗ3 ^Σ ( ^ε Η3) Ν

εΗΟ ^ζ ΗΟ ^E HO ^s HOHN

εΗΟ ^ζ ΗΟΗΝ

^{^εΗ3} ζ Η0 ε ΗΟΗΝ

εΗ3ΗΝ

[Halla 2]

One 0 I one

Z. £ 0l0 / 36df / JDd I ISf0 / f6 OAV The compounds of the present invention have systemic and extremely high herbicidal activity. As a result, the compound of the present invention can be applied to various kinds of weeds including perennial weeds in both soil treatment and foliage treatment compared to conventional herbicides. Nevertheless, it has a great feature that it quickly exerts a high effect and also has a moderate residual effect.

The compound of the present invention can be used as a herbicide for upland fields in any of soil treatment, soil admixture treatment and foliage treatment.

The application dose of the compound of the present invention varies depending on the application scene, application timing, application method, cultivated crops, etc., but is generally about 0.0001 to 10 kg, preferably 0.0001 per hectare (ha) as an active ingredient. About 5kg is appropriate.

In applying the compound of the present invention as a herbicide, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or the like, or water, alcohols (isopropanol, butanol, benzyl alcohol) , Furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, etc.), ethers (anilyl, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (E.g., N-methylpyrrolidone) or halogenated hydrocarbons (e.g., chlorobenzene), and can be used as a mixture. If desired, surfactants, emulsifiers, dispersants, penetrants, and spreading agents can be used. , Thickeners, antifreezing agents, anti-caking agents, stabilizers, etc. IF o completion Bull agents, full Roaburu, powders, can be put into practical use in granules such as any dosage form.

Further, the compound of the present invention may be mixed and used with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists, detoxifiers, etc., when necessary in the preparation or spraying.

In particular, by mixing and applying other herbicides, it is possible to reduce costs by reducing the amount of applied herbicide, expand the herbicidal spectrum by synergistic action of the mixed chemicals, and expect a higher herbicidal effect. At this time, a combination with a plurality of known herbicides is also possible. Examples of the types of herbicides used in combination with the compound of the present invention include, for example, There are compounds listed in the 1900 edition of the Calms Handbook (Farm Chemicals Handbook).

In particular, when the compound of the present invention is applied to soybeans, preferable drugs to be used in combination with the compound of the present invention include triuralin (tri ural in), pendimethalin (pendimethal in), alachlor, methacrylol (Metolachlor), metribudine (metribuzin), linuron (linuron), chlorimuron ethyl (chlorimuron ethyl). Imazaquin (imazaquin), imaze evening pinore (imazethapyr) dinoseb (dinoseb), bifunox (bifenox), roma zone, etc. Is given.

The field weeds (Cropland weeds) targeted by the present compound include, for example, Solanaceae weeds represented by Solanum nigrum and Datura stramonium, and Abut i lon theophrast i. ), Malagaceae weeds such as Side spinosa, and Asagao species (Ipomoea spps.) Such as Malva Asagao (ipomoea purpurea) and convolvulus

spps.), Amaranthus viridis (Amaranthus viridis), Amaranthus viridis (Amaranthus viridis), etc. ia), Himamari (Helianthus an drawing) ヽメギ G (Gal insoga ci lat) ィィゲ (Crisium arvense) ノボロ

Asteraceae represented by (Senecio vulgaris) and Himejon (Erigeron annus)

(Compos i tae) is Taku, Rinpapana (Rori ppa indica), Nonodara (Sinapis arvensis), Razana (CapseHa bursapastris), etc.

(Cruciferae) is a table, Inuya (Polygonum blumei) 'Polygonaceae' weeds, represented by Kazura (Polygonum convolvulus), etc.

(Portulaca oleracea) and other weeds (Portulacaceae), weeds, shiroza (Chenopodium album), sorghum (Chenopociium fi ci folium), broom Weeds (Cochopiaacea) and weeds (Cochia scoparia), Weeds (Caryophyl laceae) and weeds (Coleophyl laceae) and weeds (Veronica persica) and so on

(Scrophulariaceae) Weed, duckweed (Commel inaceae) weeds represented by communis (Commel ina communis), etc., Labiatae weeds represented by photokenosa (Lamium amplexicaule), Lamium purpureum, etc. Euphorbiaceae (Euphorbiaceae) weeds, such as Euphorbia supina and Euphorbia maculata, weeds, Galium spurium, Galium aparine and akane Representatives include Rubiaceae weeds, Violaceae weeds such as Viola arvensis, weeds, Sesbania exal tata, and Cassia obtusifol ia. Broad-leaved weeds such as Leguminosae weeds, Bidens pi losa, wild sosole gum (Sorghum bicolor), and oak millet (Pa) ni cum dichotomi f lorum), johnsongrass (Sorghum halepense), linubie (Ec inochloa crus-gal li), meji'nno ku (; Digi taria adscendens), oat (Avena fatua), and saishin hinoki (Eleusine indi ca) Graminaceous weeds such as Setaria viridis, Alopecurus aegual is, and Cyperus rotundus. Cyperus esculentus such as Cyperus rotundus. Cyperus esculentus (Cyperaceous weed). weeds).

Further, the compound of the present invention can be used as a herbicide for paddy fields in any of soil treatment and foliage treatment under flooding. Examples of paddy weeds include paddy weeds, such as Heroda mosquito (Al isma canal icu la turn), Omodaka (Sagi ttaria tri fol ia), and ゥ 'lyca (Sagi ttaria pygmaea).

(Al i smataceae) Weeds, Evening Magyari (Cyperus difformis), Mizugayari (Cyperus serot inus), Na, Evening Sole (Sci rpus juncoides), Black Kwai (Cyperaceae) weeds, such as (Eleocharis kuroguwai);

(Potenderiaceae) Weeds, Beetles (Potamogeton distinctus) and other beetles (Potamogetonaceae) and weeds, Rotala indica and so on, and Lythraceae weeds and Echinochloa (Echinochloa)

crus-galli) and other grasses (Gramineae) weeds.

The compound of the present invention can be safely used for important crops such as wheat, corn, barley, soybean, and rice.

In addition, the compound of the present invention can be applied to the control of various weeds in non-agricultural lands such as athletic fields, vacant lots, track ends, in addition to agricultural and horticultural fields such as fields, paddy fields, and orchards. (Defoliant) is also useful.

The compound of the present invention can be synthesized, for example, by the method shown in Schemes 1 and 2 (R ¹ , R ² , R ⁴ , R ⁵ , Rs, R ⁷ , R ⁸ and D ²⁶ in schemes 1 to ² are the same as those described above). G ¹ represents an alkyl group having 1 to 4 carbon atoms, G ² represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R ′ represents an alkyl group having 1 to 4 carbon atoms. Or a fluorine group.

Scheme 1

(However, R ¹ represents NH _2. )

(1) In scheme 1, the first step is to react a / 3-aminoacrylate (V) with N-phenylcarbamate (VI I) to give a peracyl derivative (Γ), and to isolate (Γ) Alternatively, a method of producing a peracyl derivative (I) by amination of the peracyl ring at position 1 as a second step without isolation.

① First stage reaction

Usually, 0.5 to 1.5 equivalents, preferably 0.8 to 1.2 equivalents, of (VI I) are used relative to (V).

The reaction usually requires a solvent, such as hexane, heptane, lignin, aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, kidylene, and chlorobenzene; Halogenated hydrocarbons such as mouth form and methylene chloride; ethers such as getyl ether, dioxane, and tetrahydrofuran; ketones such as acetone and methyl ethyl ketone; nitriles such as cetonitrile and isobutyronitrile , Pyridine, Ν, Ν — tertiary amines such as getylaniline, Ν, Acid amides such as N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, sulfur-containing compounds such as dimethylsulfoxide and sulfolane, methanol, ethanol, propanol, butanol Alcohols, water and mixtures thereof, and preferably the above-mentioned aliphatic hydrocarbons, aromatic hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof.

Usually, 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents, of the base relative to (V) is used. Nitrogen-containing bases such as pyridine, triethylamine, Ν, Ν-dimethylaniline, Ν, Ν-diethylaniline, 4- (Ν.Ν-dimethylamino) pyridine, 1,4 diazabicyclo [2.2.2] octane Organic bases, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, metal salts such as sodium methoxide, sodium ethoxide, potassium tert-butoxide Examples thereof include metal alkyl mercaptides such as rucolate, sodium methyl mercaptide and sodium ethyl mercaptide, and preferably include inorganic bases such as sodium hydride and metal alcohols such as sodium methoxide.

The reaction temperature is usually 0 to 200, and preferably from room temperature to the reflux temperature of the reaction mixture.

The reaction time usually requires 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

After completion of the reaction, (1 ′) can be isolated by acidification with a mineral acid such as hydrochloric acid, an organic acid such as acetic acid, trifluoroacetic acid, and p-toluenesulfonic acid.

② Stage 2

0.5 to 1.8 equivalents, preferably 0.8 to 1.2 equivalents, of (ミノ) is used.

Examples of the aminating agent include phenoxyamines such as 2,4-dinitrophenoxyamine and the like, and sulfonylamide α-xyamines such as mesitylenesulfonylhydroxyamine, and p-toluenesulfonyloxyamine. And chloramine. The reaction usually requires a solvent, such as hexane, heptane, lignin, stone Aliphatic hydrocarbons such as oil ethers, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, halogenated hydrocarbons such as chloroform and methylene chloride, getyl ether, dioxane, and tetrahi Ethers such as drofuran; ketones such as acetone and methylethyl ketone; nitriles such as acetonitrile and isobutyronitrile; pyridine; tertiary amines such as Ν, Ν—Νethylalanine; —Dimethylacetamide, Ν, Ν-dimethylformamide, Ν —Acid amides such as methylpyrrolidone, sulfur-containing compounds such as dimethylsulfoxide and sulfolane, and alcohols such as methanol, ethanol, propanol and butanol And their mixtures, preferably the aromatic hydrocarbons and acid amides described above. And sulfur-containing compounds and mixtures thereof.

Usually, 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents, of the base relative to (Γ) is used. Bases include pyridine, triethylamine, Ν, Ν-dimethylaniline, Ν. Ν-ethylyloniline, 4- (Ν.Ν-dimethylylamino) pyridine, 1.4 diazabicyclo [2. 2.

2] Nitrogen-containing organic bases such as octane, sodium hydride, potassium hydride, sodium hydroxide, sodium hydroxide, inorganic bases such as sodium carbonate and sodium carbonate, sodium methoxide, sodium trioxide Metal alcoholates such as methoxide and potassium tert-butoxide; metal alkyl mercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide; preferably, sodium hydride, carbonated carbonate and the like. And inorganic bases.

The reaction is carried out usually at a temperature of -30 to 200 ° C, preferably -10 ° C, at a reflux temperature of the reaction mixture.

(I) Scheme 2

(2) In Scheme 2, as the first step, N-phenylacetoacetamide (X) is closed to form an oxazine derivative (XI), and after (XI) is isolated or isolated without isolation, the second step Represents a method for producing peracyl derivative (I) by reacting with hydrazines or hydroxyamines.

① First stage reaction

The reaction usually requires a solvent, such as aliphatic solvents such as hexane, heptane, lignin, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; Mouth form, halogenated hydrocarbons such as methylene chloride, pyridine, Ν, 第三 —tertiary amines such as acetyl-niline, Ν, Ν-dimethyl cetamide, Ν, ジメチル -dimethylformamide, Ν — Acid amides such as methylpyrrolidone; sulfur-containing compounds such as dimethyl sulfoxide and sulfolane; organic acids such as formic acid, acetic acid, butyric acid, and acetic anhydride, and mixtures thereof; preferably, the above-mentioned aliphatic hydrocarbons, Aromatic hydrocarbons, halogenated hydrocarbons and organic acids.

^. The reaction is carried out usually at a temperature of 0 to 200 ° C., preferably at room temperature to the reflux temperature of the reaction mixture.

② Stage 2

0.5 to 10 equivalents, preferably 0.8 to 3 equivalents of hydrazines or hydroxylamines relative to the oxazine derivative (XI) is used. Hydrazines include hydrazine or alkylhydrazines such as methylhydrazine, ethylhydrazine, tert-butylhydrazine, 1,1-dimethylhydrazine, and the like.Hydroxylamines include hydroxylamine or methoxyamine. Rubixamines such as ethoxyamine and isopropoxyamine.

The reaction proceeds without solvent, but is usually accelerated by using a solvent. As a solvent, aliphatic hydrocarbons such as hexane, heptane, lignin, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene, halogenated hydrocarbons such as chloroform and methylene chloride Ethers, such as dimethyl ether, dioxane, and tetrahydrofuran; ketones, such as acetone and methylethyl ketone; nitriles, such as acetonitrile and isopyronitrile; tertiary, such as pyridine and N.N-ethylethylaniline Amides, N, N-dimethyl cetamide, N, N-dimethylformamide, N-methylpyrrolidone and other acid amides, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, methanol, ethanol and propanol Alcohol, water, and mixtures thereof. Better rather aliphatic hydrocarbons mentioned above, aromatic hydrocarbons, ethers, alcohols, halogenated hydrocarbons, acid Ami earth, sulfur-containing compounds and mixtures thereof like et be.

The reaction is usually carried out at -30 to 150 ° C, preferably at -10 ° C to the reflux temperature of the reaction mixture.

The reaction time usually requires 10 minutes to 96 hours, preferably 30 minutes to 48 hours. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, synthesis examples of the compound of the present invention and intermediates will be specifically described as examples, but the present invention is not limited thereto.

(Example 1)

Synthesis of 3- (4-chloro-1-5-ethylsulfonylamino 2-fluorophenyl) -6-trifluoromethyl-1,4 (1H, 3H) -pyrimidindione (intermediate)

1.06 g (5.77 mmol) of ethyl 3-amino-4,4,4-trifluorochlorotonate was dissolved in 6.2 ml of N, N-dimethylformamide, and 0.82 g (14.4 mol) of sodium methoxide was added. After 10 minutes, cool to below 5 and add 1.56 g of 4-chloro-5-ethylsulfonylamine 2-ethylfluorocarbanilide (4.81 concen- trative ol) and heat to 110 ° C. The reaction was performed for 4 hours. After the reaction, N, N-dimethylformamide was distilled off, and the mixture was dissolved by adding water, washed with getyl ether three times, and adjusted to pH 2 with concentrated hydrochloric acid to precipitate crystals. This was filtered, washed with water and dried to obtain 1.54 g (yield 77%) of the desired compound as pale yellow crystals.

Melting point 190-192 ° C 'HN RCds-DMSO) o (ppm): 1.36C3H.t.J = 7Hz) .3.12 (2H, q, J = 7Hz), 6.19 (lH, s), .44C1H, d.J = 9Hz), 7.58 C1H, d.J = 7Hz), 8.86 (lH.br s), 9.20 (1H, br s)

(Example 2)

1-Amino-3- (4-chloro-1-5-ethylsulfonylamino-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione

3- (4-chloro-1--1-ethylsulfonylamino-2-fluorophenyl) -1-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione 0.50g (1.20 ol), anhydrous To a mixed solution of 0.08 g (0.60 mmol) of potassium carbonate and 2 ml of N, N-dimethylformamide was added 0.24 g (1.20 mmol) of 2,4-dinitrophenoxyamine at room temperature, followed by stirring with stirring. After distilling off N, N-dimethylformamide, dissolve in ethyl acetate-wash with water, saturated aqueous solution of sodium bicarbonate and saturated saline, dry with anhydrous sodium sulfate and distill off ethyl acetate to obtain crude product I got something. This was purified by preparative thin-layer chromatography (developing solvent: hexane monoacetate 1: 1) to give 0.28 g (yield: 54.1%) of the desired product as orange crystals.

210 0 ~ 2 i 1 ° C ■ H-NMRCde-D SO) o (ppm): 1.34 (3H.t, J = 7Hz), 3.14 (2H, q, J = 7Hz).

4.14 (2H.br s), 5.30 (lH, br s), 6.25 (1H.s) .7.50 (1H.d.J = 9Hz),

7.63 (1H, d. J = 7Hz)

Next, a formulation example of a preparation when the compound of the present invention is used is specifically shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.

(Wettable powder)

Compound of the present invention 580 parts

Solid support 1 0 8 5 parts

Surfactant 1 110 parts

Other 1 5 copies

Other examples include an anti-caking agent.

(Milk)

Compound of the present invention 1 to 30 parts

Liquid carrier 30 to 95 parts

Surfactant 4 to 15 parts

(Floable agent)

570 parts of the compound of the present invention

Liquid carrier 1 1 5 6 5 parts

Surfactant ■ ~~ 5 1 2 parts

Other 5 3 0 copies

Other examples include an antifreezing agent and a thickener,

[Radiated wettable powder (dry flowable)]

Compound of the present invention 20 to 90 parts

Solid carrier 9 to 60 parts

Surfactant 1 to 20 parts (Granules)

Compound of the present invention 0.1 to 10 parts

Solid carrier 90 to 99.9 parts

Other 0-5 copies

[Formulation Example 1] wettable powder

Compound of the present invention (product of Example 2) ——50 parts

G-Client P F P 4 3 copies

(Riki Olin-based clay: G-Cryet Industrial Co., Ltd.)

Solpol 5050 2 parts

(Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

Lunox 1000 C 3 parts

(Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

Carplex # 80 (Anti-caking agent) 1 2 parts

(White carbon: Shionogi & Co., Ltd. product name)

The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Milk

Compound of the present invention (product of Example 2) --- 3 parts

Xylene 7 6 parts

Isophorone 1 5 parts

Solpol 3005 x 6 parts

(Mixture of nonionic surfactant and Rionionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

The above are uniformly mixed to form an emulsion.

[Compounding Example 3] Flowable agent

Compound of the Present Invention (Product of Example 2) 35 parts

AGRISOL S-71 1 8 parts (Nonionic surfactant: Kao Corporation)

Lunox 1000 C 0.5 part

(Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

1% mouth de Paul water 20 parts

(Thickener: Loan 'Poolan brand name)

Ethylene glycol (antifreeze) 1 8 parts

Water 28.5 parts

The above is uniformly mixed to form a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable)

Compound of the Present Invention (Product of Example 2) 75 parts

Isoban No. 110

(Anionic surfactant: Kuraray Isobrene Chemical Co., Ltd.)

Vanillex N 5 parts

(Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd.)

Carplex # 8 0 1 0

(White carbon: Shionogi & Co., Ltd. product name)

The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granules

Compound of the present invention (product of Example 2) —— 0.1 part

Bentonite 55.0

Talc 44. 9 parts

After the above mixture is uniformly mixed and pulverized, a small amount of water is added, and the mixture is kneaded with stirring, kneaded with an extruder and dried to form an abductant.

When used, the above wettable powders, emulsions, flowables and granular wettable powders are diluted 50 to 1000 times with water so that the active ingredient becomes 0.0001 to 10 kg per hectare (ha). Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples.

[Test Example-1] Herbicidal effect test by soil treatment

Put the sterilized flood soil in a plastic box 15 cm long, 22 cm wide and 6 cm deep, and add the following: The seeds were mixed and covered with soil about 1 cm, and then uniformly sprayed on the soil surface with a small spray so that the effective component amount became a predetermined ratio. As a chemical solution at the time of spraying, a formulation appropriately adjusted according to the above-mentioned formulation examples and the like was diluted with water and used. Three weeks after the application of the chemical, the herbicidal effect on various weeds and crops was examined according to the following criteria. Table 3 shows the results.

Judgment criteria

5—90% or more mortality (almost completely dead)

(4) Weed kill rate 70 to 90%

3 Weed killing rate 4 0 to 70%

2-Herbicidal rate 20-40%

(1) Weed kill rate 5-20%

0—less 5% weed killing (almost no effect)

However, the above-mentioned herbicidal rate was determined by the following formula by judging the above-ground fresh grass weight in the chemical treatment area and the above-ground fresh grass weight in the untreated area.

Weed kill rate = (1 above-ground fresh grass weight in one treatment area Z above-ground fresh grass weight in untreated area) X 100 The symbols in each table indicate the following.

N (Novier), M (Mehishiba), K (Ryarigusa), H (Inuhozuki), D (Hakidamegiku), I (Inugarashi), R (rice), T (corn), W (wheat), S (Soybean), C (ヮ evening) (Table 3) Compound of the present invention

Example Na (g / ha) N M K H D I R T W S C

10 5 5 5 5 5 5 4 0 0 0 3

2 20 5 5 5 5 5 5 5 0 0 0 4

40 5 5 5 5 5 5 5 1 1 0 5

Industrial applicability

The peracyl derivative represented by the formula (I) of the present invention is a compound that can be safely used for important crops and has a high herbicidal effect on many weeds, and is useful as an active ingredient of a herbicide.

Claims

-2 Claims

1. Formula (I)

Wherein, R ¹ is NR ^S R ⁷ (R ⁶ and R ⁷ each independently represent a hydrogen atom or a C, - ₄ alkyl group.), Or OR ⁸ (representative of R ⁸ is a hydrogen atom or an alkyl group.) C, represents, R ² is a - ₆ alkyl group or a triflate Ruo b methyl, R ⁴ represents water atom or a halogen atom, R ⁵ is table halogen atom or a nitro group, D ²⁶ is d- 4 represents an alkyl group or d-3 haloalkyl group. ]

A peracyl derivative represented by

2. The peracil derivative according to claim 1, wherein R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a chlorine atom.

3. The peracil derivative according to claim 1, wherein R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a bromine atom.

4. A herbicide characterized by containing the peracil derivative according to claim 1 as an active ingredient.

5. A method for controlling weed killing and growth, which comprises applying a herbicidally effective amount of the peracil derivative according to claim 1.

6 · A herbicide characterized by containing the peracil derivative according to claim 2 as an active ingredient.

7. A method for controlling weed killing and growth, which comprises applying a herbicidally effective amount of the peracyl derivative according to claim 2.

8. It is characterized in that the peracyl derivative described in claim 3 is contained as an active ingredient. Herbicide to be marked.

9. A method for weed killing and growth suppression of weeds, which comprises applying a herbicidal effective amount of the peracil derivative according to claim 3.