JPS60109578A - 3-(substituted phenyl)-5-substituted-1,3,4-oxazolin-2-one compound and herbicide containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R<1> is alkyl, alkenyl, haloalkyl, cycloalkyl, etc.; X is halogen; Y and Z are H or halogen; W is NO2, NH2, or group of formula II (R<2> is H, alkyl or aryl; A is OR<3>, SR<4> or NR<5>R<6>; R<3> is H or alkyl; R<4> is alkyl; R<5> and R<6> are H, alkyl, alkenyl, cycloalkyl, aryl, etc.)]. EXAMPLE:5-(t-Butyl)-3-(2,4-dichloro-5-nitrophenyl)-1,3,4-oxadiazolin-2 -one. USE:Herbicide. PREPARATION:The objective compound can be produced, e.g. by reacting the compound of formula III with phosgene or trichloromethyl chlorocarbonate in a solvent such as benzene, chloroform, dioxane, etc. in the presence of a base and/ or a phase-transfer catalyst (e.g. benzyltrimethylammonium chloride) at -20- +150 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel 3-substituted phenyl-S-substituted-/, 3
．． ! -Oxazinone-ones and herbicides containing them as active ingredients.

Polarized 3-phenyl or substituted phenyl-3-substituted-/
, 3. It has been reported that 'I-oxazolin-2-ones have herbicidal activity. (Refer to Tokko Sho+, 2-1:7, No. 8).

The present inventors have demonstrated that 3-@substituted phenyl-5-substituted -i,,y,
As a result of further research on lI-oxazinone-coons, it was found that the phenyl group has a halogen atom at the hi-position, a hydrogen atom or a halogen atom at the co-position and the 6-position independently, and a specific halogen atom at the 3-position. General formula with substituents (
The novel compound group shown in 1) has extremely excellent characteristics as a herbicide, that is, it has extremely strong herbicidal activity against weeds and has a wide herbicidal spectrum, while causing only minimal chemical damage to crops. This discovery led to the present invention.

That is, the gist of the present invention is as follows: General formula (wherein R1 represents a cycloalkyl group optionally substituted with a furkyl group, an alkenyl group, a haloalkyl group, an alkoxyalkyl group, or an alkyl group, X represents a halogen atom, and Y and Zf each independently a hydrogen atom or )・
2 W represents a nitro group, an amine group, or a group represented by -NH-CH-COA.

In the above substituents, Bl is a hydrogen atom, an alkyl group or an aryl group, A is a group represented by OR', a group represented by SR', a group represented by NR'R6, R4 is an alkyl group fsR1' and R6 is an alkyl group, alkenyl group, alkynyl group, alkokene group, alkynylmexy group, /chloroalkyl group, aralkyl group, or aryl group substituted with / or 2 hydrogen atoms, alkyl groups, or alkoxy groups that are the same or different from each other. show. ) 3-
ft-substituted phenyl-3-substituted-/,J,','-oxtuzoline-coons and herbicides containing the same as an active ingredient.

Next, the present invention will be explained in more detail.

3-substituted phenyl-5- represented by the above general formula (1)
Substitution-l, 3. Among the gooxazinone-ones, preferred compounds from the viewpoint of herbicidal activity are compounds in which R1 is the number of carbon atoms/-A
an alkyl group, an alkenyl group having from co to l carbon atoms, a trino-alkyl group,
romethyl group, an alkoxyalkyl group with a total number of carbon atoms of 1, or a cycloalkyl group with a total number of carbon atoms of 3 to 3 g that may be substituted with a methyl group, X is a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom, Y and Z each independently represent a hydrogen atom or a halogen atom such as a fluorine atom or a chlorine atom, W represents a nitro group, an alkyl group or a phenyl group, and A represents a group represented by OR3 or SR' group, N R' represents a group represented by R' or a saturated heterocyclic group containing a nitrogen atom, and in the above substituent, R3 represents a hydrogen atom or an alkyl group having carbon number/-4, and R4 represents a Alkyl groups fc, R1' and R6 are the same or different hydrogen atoms, alkyl groups with a carbon number of 1 - 2, a total number of carbon atoms of 2 to 9, and an alkoxy group with a carbon number of 1 - to 2-substituted alkyl group, alkenyl group with carbon number J - Q, carbon number J
-f alkynyl group, alkoxy group with -4 carbon atoms, 7 alkenyloxy groups with j-4 carbon atoms, 7-chloroalkyl group with 3 carbon atoms, methyl group substituted at the α-position carbon This is a compound showing a benzyl group, a furfuryl group, or a phenyl group, which may be a benzyl group or a phenyl group. More preferably general formula (1)
In this case, R1 is an alkyl group having about 3 to S carbon atoms, particularly a branched alkyl group such as isoprobyl group or t-butyl group, or an optionally substituted methyl group having 3 carbon atoms.
A cycloalkyl group of about 5 to 50% is preferred, particularly a cyclopropyl group.

XFi halogen, especially chlorine atom or bromine atom, Y is halogen, especially fluorine atom or chlorine atom, and 2 is preferably hydrogen atom.

2 W is preferably a group represented by -N)ICHCOA, and R2 is particularly preferably an alkyl group having 1 to 3 carbon atoms.

Further, A is preferably a group represented by NR''R6 or a saturated heterocyclic group, in which R11%R6 are the same or different and are hydrogen atoms, an alkyl group or an alkoxy group with a total number of carbon atoms of 3 to an alkyl group substituted with one alkoxy group having 1-9 carbon atoms or co-substituted alkoxy groups having 1 to 2 carbon atoms;
Alkenyl group or alkynyl group having 3 to 3 carbon atoms, alkenyloxy group, cycloalkyl group having 3 to 3 carbon atoms, benzyl group, α-methyl or α,α-dimethylbenzyl group,
Furfuryl Ms phenyl group, etc. or A is piperidino,
Morpholino, inoxazolino, tetrahydro-19
．． A 2-oxazino group or the like is preferred.

The compound represented by formula (1) of the present invention may exist as optical isomers or diastereomers depending on the case. In many cases, the isomers are obtained as a mixture containing all possible isomers. Each isomer can be obtained by various known methods (e.g.
asymmetric synthesis, synthesis using starting materials with asymmetric carbon sources, optical resolution, recrystallization or column chromatography;
It is possible to obtain this by using top chromatography (such as thin skin chromatography, high performance liquid chromatography, etc.) or a combination thereof. All of these isomers are included in the formula (summer).

The compound represented by formula (1) can be synthesized using various raw materials according to the reaction formula below.

(1) (In the reaction formula, R1, Aromatic hydrocarbons such as xylene, roform,
In a solvent or mixed solvent such as halogenated aliphatic hydrocarbons such as carbon tetrachloride, tetrachloroethane and trichlene, ethers such as dioxane and diisopropyl ether, or water, -SO~/gOc, preferably -2o-isoc
bases such as triethylamine, pyridine% dimethylaminopyridine, LN-diethylaniline, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and/or benzyltrimethyl(ethyl)ammonium. This is carried out by reacting phosgene or trichloromethyl chlorocarbonate in the presence or absence of a phase transfer catalyst such as chloride (promide) or n-butylammonium bromide (yosito).

Note that the compound of formula (11) which is a raw material can be diazotized, for example.
Reduction to the corresponding hydrazine followed by R,C0OH
Alternatively, it can be obtained by reacting with its acid halides, esters, etc.

(In the above reaction formula, RIs Xs Y, Z, and wI have the same meanings as above, and W2 represents an amine group.) Aprotic polar solvents such as formamide, dimethyl sulfoxide, N-methylpyrrolidone, sulfolane, tetrahydrofuran, and dioxane; ketones such as acetone and ethyl methyl ketone;
In solvents such as water, acetate esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, toluene, and xylene, catalysts such as iron, zinc, tin, Raney nickel, palladium black, palladium/carrier, and platinum oxide. , in the presence of acids such as acetic acid and hydrochloric acid, or in the absence of L. If no acids are present, hydrogen is introduced, and the mixture is heated at normal pressure or pressure.
r Conducted at OC.

(3) z (fV) (V) (In the above reaction formula, R1% (W3 represents a group represented by -NH-CH-COA, and R2 and A have the same meanings as above.) This reaction can be carried out without a solvent or with IN, N-dimethylformamide. , aprotic polar solvents such as dimethyl sulfoxide, N-methylpyrrolidone, and sulfolane, and aromatic hydrocarbons such as toluene, xylene, and cumene. Potassium, barium, calcium), metallic sodium (lithium, potassium), sodium hydride (
Lithium, Potassium)% Sodium (Potassium) Amide, Zinc Chloride (Lithium, Sodium, Potassium, Magnesium, Copper(1), Copper(II), Iron011)')
, sodium iodide (lithium, potassium), potassium fluoride (cesium), zinc oxide (calcium, barium, iron (II), iron dll)), lead carbonate, viridi/, terdimethylaminopyridine, triethylamine, N, N -diethylaniline.

Benzyltrimethyl(ethyl)ammonium chloride (
bromide), tetra n-butylammonium bromide (
-20-coOOC, preferably o-1qo
C (In the above reaction formula, R1, ) water, water-〆tanol, water-
In a solvent such as dioxane, in the presence of acids such as hydrochloric acid and sulfuric acid, 0
-/λOC or *gθ~/g in the presence of mep-sulfonic acid, p-toluenesulfonic acid, etc. in a solvent such as acid or acetic acid
carried out at θC = (li) n, n-dimethylformamide % N-methyl-hyroliton, co, 4', A-collidine, 6-lutedine, pyridine, etc., in a solvent such as lithium hydroxide, lithium bromide , lithium iodide, sodium iodide, etc. at 100 to -0 Or:.

(In the above reaction formula, "s , methylene chloride, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, ether, diimpropyl ether,
Acetone, ethylmethylketone, acetonitrile, pyridine, N,N-dimethylformamide, N-methyl-
In solvents such as iopyrrolidone, sulfolane, hydrochloric acid, sulfuric acid.

Phosphoric acid, methanesulfonic acid, p-)luenesulfonic acid,
Thionyl chloride, phosphorus oxychloride, methyl (ethyl) chlorocarbonate, phosgene, trichloromethyl chlorocarbonate, N,
In the presence of N'-dicyclohexylcarbodiimide, etc., sodium bicarbonate (potassium), sodium carbonate (potassium)% sodium hydroxide (potassium, barium, calcium), pyridi7,! -40-/! various alcohols, mercaptans, or amines in the presence or absence of a base such as -dimethylaminopyridine, triethylamine, N,N-diethylaniline, etc. This is done by operating in a temperature range of rθC.

forms various intermediates. It is also possible to isolate and use these intermediates in some cases.

(6) (la) [Ib] (In the above reaction formula, R1, X, Y, Z and W have the same meanings as above, at least one of Y', Y' and Y' is a hydrogen atom, and the other have the same meaning as the corresponding X, Y and Z.) This reaction is performed using acetic acid, chloroform, carbon tetrachloride, benzene,
A halogenating agent such as chlorine, bromine, sulfuryl chloride, sulfuryl bromide, N-chlorosuccinimide, N-bromosuccinimide, etc. in a solvent such as chlorobenzene, water, methanol, or ethanol or a mixed solvent at -7θ~/ kO
It is preferably carried out at a temperature range of -20-/COC.

The compound of the present invention thus obtained can be used as a herbicide as it is, but it is usually mixed with an inert liquid or solid carrier, and a suitable surfactant etc. added thereto.
It is used in the form of emulsions, powders, granules, tablets, and hydrating agents.

Liquid carriers include toluene, xylene, methylnaphthalene, cyclohexane, butanol, fIJ col,
Dimethyl sulfoxide, dimethyl formamide, acetone, methyl isobutyl ketone, animal and vegetable oils, fatty acids, fatty acid esters, water, etc., and solid carriers such as clay, kaolin clay, talc, bentonite, diatomaceous earth, silica, calcium carbonate and soy flour, Plant-based powders such as wheat flour can be opened. Furthermore, if necessary, it can be used in combination with other active ingredients such as agricultural fungicides, insecticides, nematicides or other herbicides, plant growth regulators, soil conditioners and fertilizers. Further, in order to obtain a reliable herbicidal effect, auxiliary agents such as a spreading agent, an emulsifier, a wetting agent, and a fixing agent may be appropriately mixed.

The application amount of the herbicide of the present invention varies depending on the type of compound used, target weeds, treatment time, treatment method, soil properties, etc., but usually one active ingredient is
A range of / to θ grams, preferably θ, from 3 to SO grams is appropriate.

The present inventors have discovered that the compound of the present invention exhibits high herbicidal activity in upland fields and paddy fields, while having almost no effect on crops. In other words, in the field, for example, whiteweed, pigweed, Japanese knotweed, Japanese knotweed, dogweed, purslane, leaf lily, black-and-white fern, hackberry, cyperus, cyperus, and in the paddy field, for example, azalea, commonweed, Japanese knotweed, and Japanese chickweed. It is also possible to control weeds such as Physcomitrella sinensis , Japanese grasshopper, Japanese grasshopper, Japanese grasshopper, and other weeds during the pre-emergence treatment and during the growing season. Moreover, the compound of the present invention can be used as a selective herbicide in the cultivation of crops such as rice, soybean, sunflower, cotton, potato, wheat, sugarcane, and corn.

As described above, the compounds of the present invention have the excellent property of being able to control many weeds while causing almost no harm to crops.

Furthermore, the compound of the present invention can be used against weeds that have been considered difficult to control with existing herbicides, such as field weeds, wild calla, 1. It has also been found that it has high herbicidal activity against cypress, cypress, cypress, black bream, etc. As described above, all the compounds of the present invention have the extremely excellent characteristics of having a very wide herbicidal spectrum and being highly safe for crops.

The scope of application of the compound of the present invention is not limited to the above-mentioned types of plants, and it can be used for other plants by the same application method.

Next, the present invention will be described in more detail by giving Examples and 1 part by weight.

Example 15 Synthesis of (t-butyl)-3-(co,gucyclo-5-nitrophenyl)'+3, teroxadiazolin-kone Toluene solution of phosgene (/9 w/v%) core θm
A! After cooling to ijC, 2f'i of bivaloyruco(,2,goucychloro-5-nitrophenyl)human 2jinguwa, , 2f'i was added to it while stirring, and then a mixed solution of triethylamine S-2 and hydrene/kOml was added to it.
I added it in minutes. After that, it was stirred at room temperature for 1 hour, and the /M
Pour into aqueous sodium hydrogen carbonate solution and press IF vigorously. After separating the organic N and distilling off the solvent under reduced pressure, the residue was
- Washed with hexane and dried to form the compound listed in Table 1 (A
I got 4ri37 and riV.

Synthesis of j-vinyl-3-(co,q-dichloro-5-nitrophenyl)'+3+hiro-oxadiazolin-kone/-acryloyl-co-(,2,q-dichloro-3-nitrophenyl) human 2jin-t, lfoX.

Trichloromethyl chlorocarbonate/g, gr'i was added to a mixture of toluene/ml and cooled to left C.

A mixed solution of triethylamine/triethylamine/-22 and 1 kOml of toluene was added to the mixture over 1 hour while stirring, and the mixture was stirred at room temperature for 1 hour, then poured into an i/M aqueous sodium bicarbonate solution and stirred vigorously.

After extraction with ethyl acetate, the solvent was distilled off under reduced pressure, and the entire residue was washed with n-hexane and dried to obtain the compound shown in the table (AI
), 2g 0g f gold was obtained.

Example, ys-(t-propyl)-,7-(j-aminoco,<1-dichlorophenyl)-/,? , 41-oxadiazoline-coon synthetic iron powder/0. O? , glacial acetic acid i at and water 0ml
ty) The mixture was heated to reflux for 1 hour with stirring and then cooled to gOC. In this, N-methyl-virolidonko0R1f
and then S-(/-methylethyl)-j-(,2
, $-') chloro-yo-nitrophenyl)-/, 3.
After gradually adding 'I-oxadiazoline-coon, g
The mixture was stirred at o-gzC for 7 hours.

After cooling to room temperature, potassium carbonate θ, 7 ftl was added, and after stirring for minutes, acetone was added and filtered. The resulting P solution was poured into ice water to precipitate crystals.

This was collected with tF, washed with water, and recrystallized from ethyl acetate/n-hexane to obtain the compound listed in Table 1 (A/?) 7.72.

Example DA S-Cyclopropyl-J- [Co, Tazichlor-! Synthesis of r-(/-(1-propylcarbamoyl)ethylaminocophenyl) -/, J, II-oxadiazolin-λ-one S-cyclopropyl-,7-(!r-aminocophenyl).

dichlorophenyl) -/, 3. II-Oxadiazoline-co-onco, 92, N-(1-propyl)-
After reacting a mixture of coprompropionamide q, λV and sodium hydrogen carbonate Yari V at /jθC for 7 hours,
The mixture was cooled to 30C and extracted with ethyl acetate. After washing with water and drying with Glauber's salt, the solvent was distilled off, and the entire residue was purified using a silica gel column (developing solvent: ethyl acetate-n-hexane/:3) to obtain the compound (Ak) listed in Table 1. I got an F.

Example left 5-(t-butyl)-JC ter(/-carboxylethyl)aminoco, dichlorophenyl) -/, 3. Synthesis of Q-oxadiazolin-kion 5-(t-butyl)-J-(co,4I-dichloro-r-
(/-ethoxycarbonylethyl)ami/phenyl)
-/, 3.41-oxadiaso+7 y -, 2-one/θ, lIr, methanesulfonic acid λ, Sv and formic acid l
The mixture of θθgrit was heated under reflux for 7 hours while stirring, and then cooled to room temperature. This was poured into cold water to precipitate crystals. This was taken out of the furnace, dissolved in methanol, treated with activated carbon, and the solvent was distilled off to obtain the compounds (A, ? J) listed in Table 1.
t, r r was obtained.

Example A, r-(t-butyl)-,? -[:ko, tl
-dichloro-&-(i-(N-(co,kodimethoxyethyl) -N-methylcarbamoyl]ethylamino]phenyl] -/, 3.'Synthesis of l-oxadiazoline-koone 5-(t-butyl )-, ?-[s-(/-carboxylethyl)aminoco, t-dichlorophenyl] -/,
J, II-Oxadiazoline-one Q, De4/lf
1 pyridine θ, << o y and dichloromethane, 2
3 g of thionyl chloride at 7C with stirring.
．． J J f and dichloromethane / methylaminoacetaldehyde dimethylacetal 0.3θ1, triethylamine 0.3 Of and dichloromethane j a
Add a mixture of t and stir for 0 and s hours, then further stir at room temperature for 1 hr.
．． The mixture was stirred for S hours.

After adding ethyl acetate, washing with water, and drying with sodium sulfate, the solvent was distilled off and the residue was applied to a silica gel column (developing solvent ethyl acetate-n-hexane 2=3). ! ! List of table money listed in L table 1! x
10J) 0.3 Off was obtained.

Table 1 illustrates compounds synthesized in the same manner as in Example/-A. The synthesis method used is shown in the Examples section.

All structures of the compounds listed in Table 1 were confirmed by H-NMR spectra and/or IR spectra.

Formulation Example 1 Wettable powder Compound or comparative agent listed in Table 1! θ Miyako, Hakuto Carplex #gO (trademark of Shionogi & Co., Ltd.) tS part, N,N-kaolin clay (trademark of Ueya Kaolin Co., Ltd.) 30 parts and higher alcohol sulfate ester surfactant Tsurupol toto
(Trademark of Toho Chemical Co., Ltd.) The left part was blended, mixed and pulverized uniformly to obtain an irrigation agent containing the active ingredient Yuta-chi.

Formulation example a Granules Table of formulations/2 parts of the listed compound or comparative agent, 10 parts of clay (Nippon Talc Co., Ltd. M), 55 parts of bentonite (manufactured by Houkai Yoko Co., Ltd.), Chiku/Nate yarn surfactant Nearol CT-/( Toho Chemical Co., Ltd. Trademark) λ part is mixed completely, water is added and kneaded, and granulated using a granulator. Next, this was dried at f60C for 2 hours to obtain granules containing 2% of the active ingredient.

Formulation Example 3 Emulsion 73 parts of the compound listed in Table 1 or the comparative agent was dissolved in a mixed solvent consisting of 30 parts of Kijirenda θ and 30 parts of dimethylformamide, and then the polyoxyethylene surfactant Tsurupol 3o was dissolved.
osx (trademark of Toho Chemical Co., Ltd.) Active ingredient 3 with addition of lS part
An emulsion containing 0% was obtained.

Formulation Example D Flowable Formulation 30 parts of the compound listed in Table 1 or the comparative agent were premixed with the following: 1 part of ethylene glycol, 3 parts of Tulpol AC3032 (trademark of Toho Chemical Co., Ltd.), 0.1 part of xanthan gum, and S6 water. ．． ? It is well mixed and dispersed in the parts.

Next, this slurry-like mixture was wet-milled using a sand grinder (manufactured by Igarashi Machinery Co., Ltd.) to obtain 70 samples of stable 3 parts %.

Test example / Upland soil treatment test (Part 1) Put black volcanic ash soil into a resin vat with a volume of 2.000/l.
After fertilization, dicing and wheat seeds were sown, and 23-day ridge-laying was carried out.

After seeding a mixture of the weed seeds shown in the table in this soil surface layer, an irrigation agent of each compound formulated according to Formulation Example 1 was applied.
It was diluted with water and uniformly sprayed on the soil surface using a small power pressurized sprayer to give the active ingredients shown in Table 2.

The herbicidal effect was investigated on the first day after the chemical spraying, and at the same time, the chemical damage to each crop was also investigated.

The results are shown in Table 2.

The evaluation of herbicidal effect and phytotoxicity was determined by -Y' (%), and expressed as herbicidal effect and phytotoxicity coefficient according to the following criteria.

Table 2 Test example Field soil treatment test (part 2) s, h Put volcanic ash black soil tR into a cotton pot with a capacity of 1/200, and after fertilizing, sow soybeans, cotton, and sunflowers.JIJ
The soil was weighed.

In this soil layer, there is a palmetto, which has been considered difficult to control.
After the weeds shown in Table 3, such as Ichibi and Chrysanthemum japonicum, were mixed and sown, the flowable formulations of each compound prepared according to Formulation Example 9 were diluted with water and added to the soil so that the amount of active ingredients shown in Table 3 was obtained. It was evenly spread over the surface using a small power sprayer.

Then, on the θth day after the chemical spraying, a sea bream examination was conducted for herbicidal effects and chemical damage. For comparison, the same test was carried out using the following compounds.

Comparative agent A Oh.

Comparison agent B The results are shown in Table 3.

In addition, evaluation of herbicidal power and phytotoxicity was expressed in the same manner as in Test Example.

Table 3 Test Example 3 Waterlogged soil treatment test before paddy weed emergence
Paddy alluvial clay loam was put into a resinous vat of 7000/700m, and after fertilizing, it was grown as follows:
Seeds of firefly were sown, and tubers of urikawa were buried at a depth of lα.

On the other hand, 2 plants per vat for healthy seedlings at the 3-leaf stage of paddy rice are approximately 3 c.
implanted to the depth of the IL.

The water depth was maintained at 3 cIIL, and a predetermined amount of granules of each compound prepared according to the formulation example - in the third eye after transplantation was dropped onto the water surface so as to have the active ingredient amount shown in Table D.

After the treatment, the plants were given a water reduction property of J cm 1 day for 3 days and managed in a greenhouse, and the herbicidal effect and phytotoxicity were investigated at -8 g after the treatment.

The results are shown in Table DA.

The herbicidal power and herbicidal damage were measured in the same manner as in Test Example 1.

Table S / 5 Test Example Stalk and leaf treatment test After fertilizing with black volcanic ash and soil in a 1:000 l Aruwatanel pot, all the crops and weeds shown in Table S were sown and cultivated in a greenhouse.

Japanese millet is in the 2-leaf stage, crabgrass is in the 3-leaf stage, and Japanese knotweed is in the 2-leaf stage.
．． When the 5-leaf stage, Shiroza's 2-leaf stage, the 3-leaf stage for wheat, and the co-leaf stage for soybeans, each compound formulated according to Formulation Example 3 was diluted to a volume of 10 liters of water per i/are. The amounts of active ingredients shown in Table 5 were sprayed onto grass leaves using a power sprayer.

The herbicidal effect and phytotoxicity were investigated at the 8th day after the treatment, and the results are shown in Table 5.

The herbicidal power and chemical damage were evaluated in the same way as Test 5F and Topside 1.

table!

Claims (3)

[Claims] (1) General formula (wherein R1 is an alkyl group, an alkenyl group, a haloalkyl group, an alkoxyalkyl group, or a cycloalkyl group which may be substituted with an alkyl group, and x is a cycloalkyl group which may be substituted with an alkyl group)・Rogen atom t”s Y and Z are Each independently represents a hydrogen atom or a halogen atom, and W represents a nitro group, an amine group, or a group represented by R″-NH-CH-COA. In the above substituents, R2 represents a 7JC elementary atom, an alkyl group, or an aryl group, and A represents a group represented by OR'', a group represented by SR', a group represented by N R'R', or a heterocyclic group. In the above substituents, R1 represents a hydrogen atom or an alkyl group.
4 is an alkyl group, and R1' and R6 are the same or different from each other, a hydrogen atom, an alkyl group, an alkyl group substituted with 1 to 2 alkoxy groups, an alkenyl group, an alkynyl group, an alkoxy group, an alkenyloxy group, a cycloalkyl group. group, aralkyl group or aryl group. ) J-substituted phenyl-S-substituted-ts3*4+-oxazinone-noones. (2) In the general formula (1), R1 is substituted with an alkyl group having a carbon number of /~B, an alkenyl group having a carbon number of ~Da, a trihalomethyl group, an alkoxyalkyl group having a total carbon number of a~B, or a methyl group. a cycloalkyl group having a total number of carbon atoms of 3 to 5 g, which may be
Y and 2 are each independently a hydrogen atom or a fluorine atom,
A chlorine atom, W represents a nitro group, amide, and in the above substitution, R
2 is a hydrogen atom, an alkyl group having 1 to 2 carbon atoms or a phenyl radical, A is a group represented by OR'', a group represented by SR', a group represented by NRIIR'', or a nitrogen atom! f-6-membered saturated heterocyclic group, among the above substituents,
R3 is a hydrogen atom or an alkyl group with carbon number/~R
4 is an alkyl group with carbon number/~q, R1 and R6 are the same or different hydrogen atoms, an alkyl group with carbon number 1~2, a total carbon number co~9, and an alkoxy group with carbon number/-4' Alkyl group substituted with 1 to 2 carbon atoms, alkenyl group with 3 carbon atoms, alkynyl group with 3 to 4 carbon atoms, 1 to 2 carbon atoms
O's alkoxy group, alkenyloxy group having 3 to 1/- carbon atoms, cycloalkyl group having 3 to 1 carbon atoms, benzyl group or furfuryl group which may be substituted with 1 to 5 methyl groups at the α-position carbon, or 3-substituted phenyl-j- according to claim 1
Substituted -/, 3,4'-oxazinone-ones. (3) General formula (wherein R1 is an alkyl group, an alkenyl group, a haloalkyl group, an alkoxyalkyl group, or a cycloalkyl group optionally substituted with an alkyl group '6, xi halogen atom gold, Y and 2 are each independently Hydrogen atom or )・
W represents a nitro group, an amino group, or a group represented by 1-NH-CB-COA. Among the above substituents, R2 is a hydrogen atom, an alkyl group or an aryl group, A is a group represented by OR', a group represented by SR', N R' is a group represented by R', R4 is an alkyl group, R5 and R11 are the same or different hydrogen atoms, alkyl groups, alkyl groups substituted with 1 to - alkoxy groups, alkenyl groups, alkynyl groups, alkoxy groups, alkenyloxy groups, cycloalkyl groups, aralkyl groups, or aryl groups shows. ) 3-
substituted phenyl-5-substituted-l, 3. Hiro - Oxazinone - Herbicide containing coons as an active ingredient