JPH0285269A - Oxazolidine derivative and production thereof - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R<1> is H, alkyl, cyanoalkyl, cycloalkyl, aralkyl, alkenyl, alkynyl or lower alkyloxycarbonyl; R<2> is alkyl or cycloalkyl; X<1> and X<2> are halogen). EXAMPLE:3-(2'-Fluoro-4'-chloro-5'-isopropoxyphenyl)-5-isopropyl-1,3-ox azolidine-2,4- dione. USE:A herbicide exhibiting excellent herbicidal activity against various harmful weeds and high selectivity to useful crops. PREPARATION:The objective compound of formula I can be produced by cyclizing a carbamic acid ester of formula II (R<3> is lower alkyl) in the presence of a base (e.g., sodium acetate or triethylamine) in a solvent (e.g., toluene). There is no particular restriction in the reaction temperature.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application 1] The present invention relates to a novel oxazolidine derivative having herbicidal activity. More specifically, the present invention relates to a novel oxazolidine derivative having strong herbicidal activity against various harmful weeds and high selectivity against useful crops, and a method for producing the same.

[Prior art] Derivatives having a substituted phenyl group on the nitrogen atom at the 3-position of the oxazolidine ring and various substituents at the 5-position are known, but among these derivatives, there are few practical examples. There are no derivatives with herbicidal activity (e.g. US Patent Publication 320141).
See No. 0, control compounds 1 and 2).

[Problems to be Solved by the Invention] The present invention provides novel compounds that have both high selectivity and strong herbicidal activity against various harmful weeds among oxazolidine derivatives, and furthermore, The present invention provides an industrial method for producing α-products.

[Means for Solving the Problems] As a result of intensive studies on various oxazolidine derivatives, the present inventors have determined that halogen atoms are added to the 2' and 4' positions of the phenyl ring and at the 5' position of the nitrogen atom at the 3' position of the oxazolidine ring. 1,3-oxazolidine-2,4- with ether bond introduced
The present invention was completed by discovering that dione derivatives exhibit strong herbicidal activity against various harmful weeds and high selectivity against useful crops.

[Disclosure of the Invention] That is, the present invention relates to the general formula [wherein R1 is a hydrogen atom, an alkyl group, a cyanoalkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group,
It represents an alkynyl group or a lower alkyloxylcarbonyl group, and R2 represents an alkyl group or a cycloalkyl group. The above alkyl group, cycloalkyl group, aralkyl group, alkenyl group and alkynyl group may be substituted.

Xl and X2 each independently represent a halogen atom. ] of the phenyl ring on the 3-position nitrogen atom.
The present invention relates to a novel oxazolidine derivative characterized by having a halogen atom at the `` and 4'' positions and a substituent such as an ether bond represented by an R'O group at the 5'' position, and a method for producing the same.

When the novel oxazolidine derivative of the present invention is used in rice fields, it exhibits a strong herbicidal effect against annual weeds such as Japanese barnyard grass, Japanese grasshopper, and Japanese grasshopper, as well as perennial weeds such as Cyperus japonica, Firefly, Uricula spp. Even in fields, it is possible to selectively kill field weeds such as goldenrod, Japanese grasshopper, foxtail grass, whiteweed, knotweed, blueberry, purslane, and plantain.

Furthermore, the compounds of the present invention have strong weedicidal activity, and not only can initial effects be obtained with a small amount, but also have extremely low phytotoxicity to useful cultivated plants. In other words, the chemical of the present invention kills weeds of the grass family such as barnyard grass, grasshopper, and foxtail grass, but does not cause almost any chemical damage to transplanted rice, wheat, corn, etc., which are grass family crops. Similarly, almost no phytotoxicity is observed on crops other than the family, such as soybeans and cotton.

The amount of the herbicide containing the herbicide of the present invention as an active ingredient varies depending on the application method, timing, type of target plant, etc., but the amount of the compound is 10 to 500 g per 10 ares, preferably about 30 to 300 g. be.

According to the present invention, the novel oxazolidine derivative represented by the above formula (+) can be produced, for example, by the method shown in the following reaction formula.

1 (In the formula, Rl, R2, R3, It can be manufactured using the following method.

Preparation of Mim↑'1 (In the formula, R", R2, R', X' and X2 have the same meanings as above. Y is a leaving group.) Production method 3 (In the formula, Rl, R2 , R), χ1 and X2 have the same meanings as above. Z is an incyanato group or a salt f
Represents a hycarbamoyl group. ) Production method 2 of raw fil'' (wherein R1, l' (2, R5, R!, (In the formula,
R', R'', It', R', R', X- and X2 have the same meanings as above.) In the above and below descriptions of this specification, various Preferred examples and explanations of definitions are detailed below.

Suitable [alkyl groups] are linear or branched alkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, and inpropyl groups.

Butyl group, t-butyl group, 9ee-butyl group, pentyl group, 3-pentyl group, hexyl group, 2-hexyl group, octyl group, dodecyl group, 2-dodecyl group, hexadecyl group, octadecyl group, octyl group, etc. Preferably, it has 1 to 1.2 carbon atoms.

Suitable "cyanoalkyl groups" are linear or branched cyanoalkyl groups having 1 to 4 carbon atoms in the alkyl moiety, such as cyanomethyl groups, 1-cyanoethyl groups,
Examples include 2-cyanoethyl group and 3-cyanopropyl group, but preferably 1 carbon atom in the alkyl moiety.
~2 pieces. The cyano group may be substituted at the terminal or other than the terminal of the alkyl group.3 Suitable "cycloalkyl groups" are cyclic alkyl groups having 1 to 12 carbon atoms, such as cyclopropyl group, cyclopentyl group. , cyclohexyl group, cyclooctyl group, cyclododecyl group, etc., but preferably 1 carbon atom
~6 pieces.

Suitable "aralkyl groups" are aralkyl groups such as benzyl group and α-phenethyl group, and the phenyl group is a halogen atom such as fluorine, chlorine or bromine, such as methyl group, ethyl group, proyl group, isopropyl group, Lower alkyl groups such as butyl group, butyl group, e.g. methoxy group, ethoxy group, propoxy group, inpropoxy group,
It may be substituted with one or more substituents such as a lower alkoxy group such as L-butoxy group or a nitro group.

Suitable "alkenyl groups" are linear or branched alkenyl groups having 3 to 10 carbon atoms, such as allyl, methallyl, propenyl, butenyl, pentenyl, hexenyl, prenyl, geranyl, Neryl group etc. can be obtained.

Suitable [alkynyl group j is a straight chain or branched alkynyl group having 3 to 8 carbon atoms, 10 pargyl group, ■-methylpropargyl group, 1.1-dumenal 1
Examples thereof include 0pargyl group, 1-ethylpropargyl group, 2-butynyl group, 3-butynyl group, 2-pentynyl group, and 3-pentynyl group.

"Lower", unless otherwise specified, shall mean groups having 1 to 6 carbon atoms. Therefore, examples of the [lower alkoxycarbonyl group] include methoxycarbonyl group, ethoxycarbonyl group, inbutyloxycarbonyl group, hexyloxycarbonyl group, and the like.

"As the halogen atom J, fluorine atom, chlorine atom, bromine atom, or iodine atom may be mentioned, but fluorine atom, chlorine atom, or bromine atom is preferred as a suitable example of the "leaving group" of "Y" Examples include halogen atoms such as fluorine atom, chlorine atom, bromine atom or iodine atom, substituted sulfonyloxy groups such as trisulfonyloxy group, phenylsulfonyloxy group and methylsulfonyloxy group.

"Z" represents an isocyanate group or a carbamoyl chloride group.

Next, the oxazolidine derivative represented by the above formula (1), which is a compound of the present invention! ! 8! The manufacturing method will be explained in detail below.

Missing 1 L↓! Iλ Tomo - Compound a of the present invention (1) can be produced by a cyclization reaction of a carbamate ester represented by formula (II) -a.

Reactions are usually carried out in the presence of a base. Suitable bases include, for example, tertiary amines such as l-ethylamine, tripropylamine, tributylamine, N-methylmorpholine, dimethylaniline, aromatic amines such as pyridine, lutidine, pyrimidine, sodium methoxide, sodium ethoxy 1, an alkali metal alkoxide such as potassium-L-butoxide, an alkali metal hydride such as sodium hydride, hydroxide, or carbonate, potassium carbonate, sodium hydroxide, hydroxide Basic inorganic metal salts such as sodium acetate, potassium acetate, lithium acetate, etc. can be used.

This reaction is carried out in an organic solvent. Suitable organic solvents include aromatic solvents such as benzene, [-toluene, and xylene, ether solvents such as dioxane, tetrahydrofuran, and dimethoxyethane, alcohol solvents such as methanol, ethanol, and impropatol, and ethyl acetate. , dimethylformamide, dimethyl sulfoxide, acetonitrile and the like, but the reaction can be carried out in any other solvent as long as it does not adversely affect the reaction.

The reaction temperature is 1! but not limited to, usually room temperature, heating, heating,
Alternatively, the reaction is carried out under heating under reflux in the solvent used.

After completion of the reaction, the product can be obtained by conventional post-treatment, and if necessary, it can be purified by column chromatography, recrystallization, etc.

Establishment Punishment 93 Biographies - In this production method, - Among the compounds of the present invention represented by the formula (1), carbonic acid esters represented by R″oC as R′ are C1 of the hydroxyl group, and have a carbonic acid ester as a protecting group. It is made from an oxazolidine derivative (I゛). That is,
The carbonate ester of compound (d) is treated under basic conditions to obtain a phenol derivative represented by -max (d°) or its alkali gold sample salt, and then this is combined with the phenol derivative represented by formula (I[[)]. The oxazolidine derivative represented by the following formula is produced by reacting with an alkylating agent. The original Itth product (bi) in this production method
and the reaction intermediate (bi) are both new and have the general formula (
It is included in the present invention & product shown in 1).

The hydrolysis reaction of the carbonate ester is carried out in the presence of a base, and is characterized by selectively hydrolyzing only the carbonate ester under basic conditions such that the oxazolidine ring is not hydrolyzed. Suitable bases include metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, etc.
Examples include alkali metal hydroxide monoarsenides such as sodium hydroxide, potassium hydroxide, and monohyrlithium hydroxide, and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and lithium methoxide. The amount of base used is preferably 0.5 to 2.0 equivalents relative to the substrate.

The reaction is carried out in common organic solvents, including methanol,
It is preferable to carry out the experiment in a protic solvent such as ethanol, isopropyl alcohol, butanol, and aromatic solvents such as benzene, toluene, xylene, ether solvents such as dioxane, tetrahydrofuran, dimethoxyethane, or dimethyl Aprotic solvents such as formamide and dimethyl sulfoxide can also be reacted in a mixed solvent with a protic solvent as long as they do not adversely affect the reaction.

Next, the compound (1'') of the present invention can be produced by reacting the oxazolidine derivative (I'') obtained in this way with a compound represented by -maximum (III). can.

This reaction is carried out in the presence of a base.

For example, tertiary amines such as triethylamine, tripropylamine, tributylamine, N-methylmorpholine, dimethylaniline, aromatic amines such as pyridine, lutidine, pyrimidine, sodium methoxide, sodium ethoxide, potassium L-butoxide. Alkali metal alkoxides such as sodium hydride, alkali metal hydrides such as potassium hydride, or sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, hydroxide (
Basic mineralization a, such as hysodium, potassium hydroxide
carboxylic acid gold salts such as sodium acetate, potassium acetate, lithium acetate, alkyl lithium reagents such as methyl lithium, +1-butyl lithium, or alkali metal amides such as sodium amide and lithium amide. can.

Preferably, the reaction is carried out in an organic solvent. Suitable organic solvents include aromatic solvents such as benzene, toluene and xylene, ether solvents such as diethyl ether, dioxane, tetrahydrofuran and dimethoxyethane, ketones such as acetone and methyl ethyl ketone, acetonitrile,
Nitriles such as inbutyronitrile, organic solvents such as ethyl acetate, N,N-dimethylformamide, dimethyl sulfoxide, and sulfolane, or mixed solvents thereof can be used.

In addition, when a salt arsenide, bromide, or sulfonic acid ester is used as the compound represented by the general formula ([11)] in this reaction, depending on the compound, iodides such as sodium iodide or sodium iodide, or tetra - The progress of the reaction can be accelerated by adding a quaternary ammonium salt such as laethylammonium bromide, benzyltriethylammonium bromide or iosite.

The reaction temperature varies depending on the base or solvent used, but is not particularly limited, and the reaction may be carried out under cooling, at room temperature, under heating, or under heating.

After completion of the reaction, the product can be obtained by conventional post-treatment, and if necessary, it can be purified by column chromatography, recrystallization, etc.

Furthermore, in carrying out this reaction, a metal salt of compound (1'') of phenol can be used. This metal salt is (
It can be obtained by treating the compound (d) or the alpha compound (d) with a base, but in either case it can be used in the next reaction whether or not it is isolated from the reaction system.

Invention 1 (1) is a derivative in which a methylidene group is substituted with 5 (i) and a methylidene group is substituted with a double bond under hydrogenation conditions. It can be produced by hydrogenating.

A normal olefin reduction reaction can be used for this reduction reaction, but it is possible to use a common olefin reduction reaction. carbon, platinum oxide, lye
- Unrestricted contact such as Ningel, etc.) with catalysts, palladium
A homogeneous hydrogenation catalyst consisting of a J1m transfer metal J8 tree such as ROJIN, IRIJI, RUTHENIU 11, etc. can be used.

This reaction is preferably carried out in an organic solvent. Suitable V1 solvents include alcoholic solvents such as methanol, ethanol, inglobanol, ethylene glycol, benzene, toluene, xylene, etc., although they vary depending on the catalyst used. Aromatic solvents such as ethereal solvents such as silyl ether, dioxane, tetrahydrofuran, dimethoxyethane, organic solvents such as ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and imbutyronitrile, or Mixed solvents thereof can be used. Particularly when using a heterogeneous catalytic hydrogenation catalyst, it is preferable to use an alcohol solvent from the viewpoint of yield and selectivity.

Although the reaction proceeds satisfactorily even at normal hydrogen pressure, the reaction time can be shortened by carrying out the reaction under hydrogen pressure of about several atmospheres.

After the completion of the reaction, the hydrogenation catalyst can be recovered by filtration, and the product can be obtained by normal post-treatment, but if necessary, it can be purified by column chromatography, recrystallization, etc.

Next, the method for producing the raw material compound will be explained in detail below.

The carbamic acid ester derivative represented by the maximum (II) of 8-1 is obtained by combining an aryl isocyanate or carbamoyl chloride represented by the -ffi formula (V) with a tz-hydroquine carboxylic acid ester represented by the general formula (Vl). It can be produced by reaction.

This reaction is usually carried out in the presence of a base. Suitable bases include, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, alkalis such as sodium helium methoxide, sodium methoxide, ethoxide, lithium methoxide, potassium t-butoxide, etc. Base ash alkoxide, triethylamine,
Tertiary amines such as tripropylamine, tributylamine, N-methylmorpoline, dimethylaniline, etc., aromatic amines such as pyridine, lutidine, pyrimidine, etc. can be used.

This reaction is carried out in an organic solvent. Suitable organic solvents include aromatic solvents such as benzene, toluene, and xylene; ether solvents such as diethyl ether, dioxane, tetrahydrofuran, and dimethoxyethane;
Organic solvents such as ethyl acetate, dimenalformamide, dimethylanilinde, and acetonyl-lyl can be used, but the reaction can be carried out in any other solvent as long as it does not adversely affect the reaction.

The reaction temperature is not particularly limited, and is usually room temperature, cured product, heating,
or (:E m The reaction is carried out under heating under reflux with 7 g of medium J
>lL.

After the completion of the reaction, product 3 can be obtained by conventional treatment, but if necessary, color 11 chromaography,
Tn'lJ by recrystallization or the like.

The carbamate derivative represented by the tongue+1-/IZ formula (f[) of production method 2 to If' is the known f described in JP-A-62-174065.
A carbamic acid ester derivative having a double bond in the molecule represented by the general formula (■), which is a hydrogen compound, has one hydrogen atom f ↑
It can be produced by hydrogenating the double knot underneath.

For this reduction reaction, a normal olefin reduction reaction (11m
However, heterogeneous catalytic hydrogenation of palladium carbon, palladium blank, palladium asbestos, palladium\silica, palladium alumina, rhodium, carbon, rhodium asbestos, rhodium silica, rhodium alumina, platinum carbon, platinum oxide, Raney nickel, etc. A catalyst or a homogeneous hydrogenation catalyst made of a transition metal such as palladium, rhodium, iridium, or rhdenium can be used.

This reaction is preferably carried out in an organic solvent.

Suitable organic solvents vary depending on the catalyst used, but include alcoholic solvents such as methanol, ethanol, in-10panol, and ethylene glycol, aromatic solvents such as benzene, toluene, and xylene, dienal ether,
Ether solvents such as dioxane, tetrahydrofuran and dimethoxyethane, organic solvents such as ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and imbutyronitrile, or mixtures thereof can be used. Particularly when using a heterogeneous catalytic hydrogenation catalyst, it is preferable to use an alcohol solvent from the viewpoint of yield and selectivity.

Although the reaction proceeds satisfactorily even at normal hydrogen pressure, the reaction time can be shortened by carrying out the reaction under hydrogen pressure of about several atmospheres.

After the completion of the reaction, the hydrogen (hydrogen) catalyst can be recovered by filtration, and the product can be obtained by ordinary post-treatment, but if necessary, it can be purified by column chromatography, recrystallization, etc.

In this way, one of the most important expressions of the present invention that can be achieved is (
Typical oxazolidine derivatives represented by r) are shown in Section 3, 1k.

Table 1 Oxazolidine Derivatives Table 1 Oxazolidine; ^ Water Conduction (Continued) The present invention will be explained in more detail below with reference to Examples and Production Examples.

Okawa” LL [Compound 1] (240 mg, yield 55%) was obtained.

Ethyl 2-(N-<2'-fluoro-4'-chloro-5'-isopropoxyphenyl)carbamoyloxy)isovalerate (500 mg, 1.
A catalytic amount of sodium acetate was added to a solution of 33 mmol) in toluene <30 ml, and the mixture was stirred under reflux for 5 hours.

After the reaction was completed, the solution was washed with I N t=acid, and the organic layer was dried and the solvent was distilled off under reduced pressure. The obtained oil was purified by silica gel column chromatography (eluent: ethyl acetate/hexane-1□710) to obtain pure 3-(2'-fluoro-4°-chloro-5'-isopropoxyphenyl). -5-yne 10-pyl-1,3-oxazolidine-2,4-ditertiary-(2'-fluoro-4°-
Riroro 5'-isopropoxyphenyl)-5-isopropylidene 1,3-oxazolidine-2,4-dione (
400 export S.

A catalytic amount of 10% P d/C (80119) was added to a solution of 1,22 mmo I) in ethanol (30 zl), and the reaction was carried out at room temperature under a hydrogen atmosphere at normal pressure until the absorption of hydrogen gas stopped. The catalyst was separated and the liquid was concentrated under reduced pressure to obtain a colorless and transparent oil.Then, this product was purified by silica gel column chromatography (elution?i!: ethyl acetate/hexane = 1/10). In particular, pure 3-(2'-fluoro-4°-
Chloro-5-inpropoxyphenyl)-5-isopropyl-13-oxazolidine 2,4-dione [Compound 1
] White crystals (310I+y, volume 7796) were obtained.

2.4-Dichloro-5-yne 10-boxyphenyl isocyanate (1,0y, 4.06mwo) and ethyl 2-hydroxyynevalerate (890+B, 6.09nnol)
) in toluene (50zt') was stirred at 80°C for 3 hours.

The incyanate completely disappeared from the IR and 'H-NMR spectra of the hot reaction product, and the adduct, 21N-<2.4'-dichloro-5-
It was confirmed that ethyl (impropoxyphenyl)carbamoyloxy)isovalerate was produced. Then, a catalytic amount of sodium/lium acetate was added, and the solution was stirred for 5 hours under heating under reflux. After washing with acid and drying the V1 layer, it was concentrated under reduced pressure. The obtained oil was purified with silica gel caranoide and 20 madography (eluent: ethyl acetate/hexane; 1/10) to obtain pure 3-(24゛-dichloro-5°-isopropoxyphenyl) 5- Isopropyl-1,3-oxazolidine2.
4-dione [chemical & compound 2] (470I6i?, +(! rate 3
3%).

Fire level 1L 21N-(2'-fluoro-
Ethyl 4-chloro-5°-cyclopentyloxyphenyl)carbamoyloxy)-3-methyl-3-butenoate (
800mg, 2.0m+*ol) of toluene (30zZ
) A catalytic amount of sodium acetate was added to the solution and stirred under reflux for 3 hours. After the reaction was completed, the solution was washed with IN hydrochloric acid, the organic layer was dried, and the solvent was distilled off under reduced pressure. The obtained oil was purified by silica gel column chromatography (eluent: ethyl acetate/hexane 115) to obtain pure 3=(2°-fluoro-4′-chloro-5′-cyclopentyloxyphenyl)-5. -Impropylidene 1.
White solid of 3-oxazolidine-2,4-dione (54
0B, yield 76%). 'H-NMR (CD CI
,,TMS, δp+oa): 1.58-1.91(
811, m) 2.00 (311, s), 2.26 (3
11, s), 4.73 (ill, n), 6.77
(ill, d) 7.27 (ill, cl); I
R(K B rdisk, cu-'): 1820.

1743.1693; MP: 98-99.5°C6 Next, the thus obtained 3-(2'-fluoro-4'-chloro-5'-cyclopentyloxyphenyl)-5-inpropylidene-1 ,3-oxazolidine 2,4-dione (500B, 1.41 mmol) in ethanol (3C
1+1> A catalytic amount of 10% Pd/C (100rgy
) was added, and the reaction was allowed to proceed at room temperature under a hydrogen atmosphere at normal pressure until absorption of hydrogen gas stopped. After the reaction is complete, separate the catalyst from P
The liquid was condensed under reduced pressure to obtain a colorless and transparent oil. Then, a small amount of methanol was added, and after cooling, white crystals were precipitated (360 mg, yield 72%). This product is the desired 3-(2-fluoro-4'-chloro-5'-cyclopentyloxyphenyl)-5-yne 10vir-1,3-oxazolidine-2,4-dione [Compound 3
] was confirmed by spectra etc.

1 inhibition-3-(2'-fluoro-4°-chloro-5'-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione (700+o&, 2.43mmo
Potassium carbonate (340 rag) was added to a solution of 1) in acetonitrile (30++1) and stirred under reflux for 1 hour.

Then, propargyl bromide (2zf) was added and the mixture was further stirred under reflux for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, IN hydrochloric acid was added, and the mixture was extracted with ether.

After drying the organic layer, the solvent was distilled off under reduced pressure to obtain a pale yellow oil. This product was purified by silica gel column chromatography (eluent:!!il: ethyl acid/hexane = 1/10) to obtain pure 3-(2
-fluoro-4"-chloro-5°-propargyloxyphenyl)-5-isopropyl 1,3-oxazolidine-2,4-dione [compound 4] (480 s2 yield 61
%) was obtained.

E1 Propoxyphenyl)-5-(2”-butylidene)1.
3-oxazolidine-2,4-dione (300B, 0.
A catalytic amount of 10% Pd/C (60 rag>) was added to a solution of 88 mmol) in ethanol (30 ml), and the reaction was carried out at room temperature under a hydrogen atmosphere at normal pressure until the absorption of hydrogen gas stopped. The separated rrnα was concentrated under reduced pressure to obtain a colorless and transparent oil.

This product was then subjected to silica gel column chromatography (eluent: ethyl acetate 7.'hexane-17.'10).
Pure 3-(2'-fluoro-4'-chloro-5°-ingloboxyphenyl)-5 was purified by
-(2°′-Butyl”)-1,3-oxazolidine-2
,4-dione [compound a 5] (240B, yield 80%)
I got it.

Tue 1 Takumi L 3-(2'-fluoro-4゜chloro-5゜-iso According to the method of production example, 2-fluoro-4-chloro-5
2-(N-(2°-fluoro-4'-chloro-5'-isopropoxyphenyl)rubamoyloxy prepared from -improboxyphenylisocyanate and ethyl 2-hydroxy-2-cyclopentylacetate) )-2-cyclopentyl acetate menal (400+@y, 1.0+uao
A catalytic amount of sodium acetate was added to a solution of 1) in N,N-dimethylformamide (30 zl), and the mixture was stirred at 50°C for 8 hours. After the reaction was completed, IN hydrochloric acid was added to the solution and extracted with ether. The ether layer was washed three times with IN hydrochloric acid, dried and concentrated under reduced pressure. The obtained oily substance was purified by 20 silica gel column (elution) ethyl acetate/'hexane-1/10), and further recrystallized from methanol to obtain pure 3=(2°-fluoro-4'- 4 low 5
°-isopropoxyphenyl)-5-diclopentyl-
1,3-oxazolidine-2,4-dione [compound 6] white solids (170+++ g, yield 48%) were obtained.

Real JlfL oily (approximately 60%) sodium hydride (170my25
After washing 3-(2'-fluoro-4°-chloro-5°-hydroxyphenyl)5-isopropyl-1,3-oxazolidine 24-dione (1 ，
0y, 3.48 wheels (01) was added, and the mixture was stirred at room temperature until hydrogen generation stopped. 3-( by removing the solvent
A white solid of 2°-fluoro-4-lichloro-5°-storiumoxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione was obtained. Ethyl iodide (2xl) was added to an acetonitrile solution <30d) of this product and stirred under reflux for 3 hours.After the reaction was completed, IN hydrochloric acid was added and extracted with chloroporum. A pale yellow oil is obtained by removing 11.

By recrystallizing this from methanol, 3i2
'-Fluoro-4'-chloro-5-ethoxyphenyl)
-5-inpropyl-1,3-oxazolisone-2,
4-Sion [1hi group 1 course 7] (700tng yield 6
4%).

Aim 11υ A colorless and transparent oil was obtained by concentrating to the bottom.

Then, the desired 3-(2°-fluoro-4′-chloro-5°hexyloxyphenyl)-5-isoalrobyl 1,3-oxazolidine-2,4-dione [1] was recrystallized from methanol. 8] (330+ay
, yield 66%).

Hiseho-10- 3-(2'-Fluoro-4'-chloro-5'-hexyloxyphenyl)-5-isopropylidene 1,3-oxazolidine-24-dione (500 s, 1.35 scale 5 o
Add a catalytic amount of 10% P to the ethanol <30 ml solution of l).
d/C (100 m1t) was added, and the reaction was allowed to proceed at room temperature under a hydrogen atmosphere at normal pressure until absorption of hydrogen gas stopped. After the reaction is completed, the catalyst is separated from each other and P liquid 3 is depressurized 3-〈2°-fluoro-
4'-Chloro-5'-methoxycarbonyloxyphenyl)-5-isopropyl-1,3-oxazolidine-2
,4-dione (15.2 g, 44.0-mol) in dry methanol (150 zl) with potassium carbonate <3.0
4y, 22.0 +++ mol) was added thereto and stirred at room temperature for 3 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ether.

After drying the ether layer, the solvent was distilled off under reduced pressure to obtain a pale yellow oil. This product was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane = 1
3-(2'-Fluoro-4°-chloro-5°-hydroxydiphenyl)-5
-Isopropyl-1,3oxazolidine-2,4-dione [Compound 14] (10.5g, yield 83%) was obtained.
Next, this phenol derivative (700-g, 2.43 mm
Allyl bromide (2 ml) and potassium carbonate (3401111?) were added to a solution of ol) in acetonitrile (30d) and stirred under reflux for 3 hours. 6 After the reaction was completed, the solvent was distilled off under reduced pressure, IN hydrochloric acid was added and extracted with ether. did. Dry the organic layer? & The solvent was distilled off under reduced pressure to obtain a pale yellow oil.

This product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane-1/10) to obtain pure 3-(2°-fluoro4°-chloro-
5°-allyloxyphenyl)-5isopropyl-1,
3-oxazolidine-2,4 dione [monster 9] (54
0 mg, yield 68%).

LargeILLL 3-(2°-fluoro-4°-chloro-5-methoxycarbonyloxyphenyl)-5-isopropyl-1,3
-oxazolidine-2,4-dione (800B, 2.3
Potassium carbonate (160B, 1.16 mol) was added to a solution of 11 mol) in dry methanol (30*j'), and the mixture was stirred at room temperature for 2 hours. Then, the solvent was distilled off under reduced pressure, and acetonitrile (30z1) and allyl bromide (2
z1) was added and stirred under reflux for 3 hours.

After the reaction was completed, the solvent was distilled off under reduced pressure, IN hydrochloric acid was added, and the mixture was extracted with ether. After drying the ether layer, the solvent was distilled off under reduced pressure to obtain a pale yellow oil. By purifying this product by silica gel column chromatography (eluent: ethyl acetate/hexane = 1/IQ), 3-(2'-fluoro-4'-chloro-5'-allyloxyphenyl) = 5-yne 10 Pyr-1,3-oxazolidine=2,4-dione [Compound 9] (240MIF
, yield 32%).

Potassium carbonate (34Q+@g) was added to the N,N-dimethylformamide solution of LL2 Yupeng, and the mixture was stirred at 70°C for 40 minutes. Then add methallyl chloride (2.0a1) and add 70
Stirred for an additional 12 hours at .degree. After the reaction was completed, IN hydrochloric acid was added to the solution, and the mixture was extracted with ether.

The ether layer was washed three times with IN hydrochloric acid, the organic layer was dried, and the solvent was distilled off under reduced pressure to obtain a pale yellow oil. This product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane-1/10) to obtain pure 3-(2fluoro-4°-chloro-
5゛-methallyloxyphenyl)-5-yne 10vir-
1.3-Oxazolidine-2,4-dione [Compound 10
] A colorless transparent oil (480 mII, yield 58%) was obtained.

E1 life 11 3-(2'-Fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione (700 mg, 2.43 Examples By the same operation as shown in 5, 3-("2'
-fluoro-4″-chloro-5°-hydroxyphenyl>-5-isopropyl-1,3-oxazolidine-2,
'3-(2'-Fluoro4'-chloro-5'-dodecyloxyphenyl)5-isopropyl-1,3-oxazolidine 2.4- from 4-dione (700B, 2.43++ aol) and 1-iodododecane Dione [Compound 11
] (760+self g, yield 69%) was obtained.

Friend 1 Salmon destination 10? Add Pd/'C (100 g) and react at room temperature under a hydrogen atmosphere at normal pressure until absorption of hydrogen gas stops. After the reaction is complete, remove the catalyst and concentrate the p liquid under reduced pressure. This gave a colorless and transparent oil.

This product was then purified by silica gel column chromatography (eluent: ethyl acetate/hexane-1/10) to obtain pure 3-(2'-fluoro-4'-
A colorless transparent oil of chloro-5°-dodecyloxydiphenyl)-5-isopropyl-1,3-oxazolidine 2,4-dione (compound 11) was obtained (420 ml, yield 84%).

3-(2'-fluoro-4'-chloro-5'-dodecyloxyphenyl)-51 sobropylidene 1,3-oxazolidine-2,4-dione (500mg, 1, 1
A catalytic amount of 3-
(2°-fluoro-4°-chloro-5°-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione (800u+y, 2.78m+nol
) and (1-promoenal)benzene 3 i2'
-Fluoro-4'-ri4-5'-(1'-phenylethyl)oxyphenyl)-5-isopropyl-13oxazolidine-2,4-dione [1H:'I'1ll1
2] (490+II!?, yield 45?≦) was obtained.

1bL Color Loli 3-(2'-Fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-2,11-dione (700B, 2.43 mIIo
I) N,N-dimethylformamide (3011)
Add potassium carbonate (340 mg) to the solution and heat at 70°C for 4 hours.
The mixture was heated and stirred for 0 minutes. Then 2-iodododecane (0,7
iZ) was added, and the mixture was further stirred at 70°C for 12 hours.

After completion of the reaction 10 IN hydrochloric acid was added to the solution and extracted with ether. Wash the ether layer three times with IN hydrochloric acid and dry the organic layer.
If the solvent was distilled off under reduced pressure, a pale yellow oil was obtained. This was mixed with Zilica gel carano, Chroma 1 Hegelafy (eluent ethyl acetate/hexane-1/'1)
0) to obtain pure 312′-fluoro-11°-chloro-5′(2°°-dodecyl)oxyphenyl)-5-isopropyl-1,3-oxazolidine-2,tl-dione [f A colorless and transparent oil (490+ay, yield 44%) of compound 13 was obtained.

Okawa I Hikiage 1-3-(2-fluoro-4°-chloro-5°-hydroxyphenyl)-5-yne 10pylidene-1,3oxazolidine-2,4-dione (2001mg).

A catalytic amount of 10% Pd/C (40 u) was added to a solution of 0.70 m5 ol) of ethanol (20 d), and the reaction was carried out at room temperature under a hydrogen atmosphere at normal pressure until the absorption of hydrogen gas stopped.
After the reaction was completed, the catalyst was evaporated and the furnace liquid was concentrated under reduced pressure to obtain a colorless and transparent oil.This product was then subjected to silica gel column chromatography (eluent: ethyl acetate/hexane = 1/10). Purification yields pure 3-(2°-fluoro-4°-chloro-5°-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine 2,4-dione [Seven Kimono 14] (180% , yield 89%).

Ethyl oxyphenyl)carbamoyloxy)isovalerate (24.5 g, 62.5 mmol) 77) Toluene (
200z &> Touch the solution v1. After the completion of the reaction, IN hydrochloric acid was added to the solution and extracted with ether. The organic layer was washed three times with IN hydrochloric acid, dried and concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (elution overnight, ethyl acetate/hexane-1/3) to give 3(2-fluoro-4°-chloro-5°-methoxycarbonyloxyphenyl)-5- In 10 Building 1.3-Oxazolidine-
2,4-dione [compound ¥(Is 15 ](15,21
1, yield 7o%).

2-(N-(2°-Fluoro-4'-chloro-5'-methoxycarbonyl 3-(2
'-Fluoro-4'-chloro-5'-methoxycarbonyloxyphenyl)-5-impropylidene-1,3-
Oxazolidine-2,4-dione (370 mg, 1.0
A catalytic amount of 10% Pd/C (80 μl) was added to a 30 μl phosphorus solution of 8 + usol), and the reaction was carried out at room temperature under a hydrogen atmosphere at normal pressure until the absorption of hydrogen gas stopped. After completion of the reaction, The catalyst was separated from the furnace and the furnace liquid was concentrated under reduced pressure to obtain a colorless and transparent oil.This product was then subjected to silica gel column chromatography (eluent: ethyl acetate/
Pure 3-(2°-fluoro-4°-chloro-5°-methoxycarbonyloxyphenyl)-5-isopropyl-1,
3-Oxazolidine-2,4-dione [Compound 15] (
35011 g (yield 94%) was obtained.

11 Salmon I was added to 3 (2゛-
Chloro-4°-ri-4ro-5°-hydroxyphenyl)-
5-isopropyl-1,3-oxazolidine-2,4-
3-(2°-chloro-4°-
Chloro-5'-propargyloxyphenyl)5-yne 10vir-1,3-oxazolidine 2,4-dione [Compound 16] (264 mg, yield 81%) was obtained.

Large m (Compound 16) 3 (2°, 4
°-dichloro-5°-hydroxyphenyl)5-(2”
-hexyl)-1,3-oxazolidine-2,4-dione (350 s, 1.0+a++ol) and propargyl bromide, 3-(2',4'-dichloro5-propargyloxyphenyl)-5 -(2'“hexyl)-1
,3-oxazolidine-2,4-dione [Compound 17
] (3151117, yield 82%) was obtained.

3(2°-
Fluoro-4'-fluoro-5'-hydroxyphenyl)-5-inpropyl-1,3-oxazolidine-2,
From 4-dione (878+B, 3.25m+5ol) and propargyl bromide, 3-(2'-fluoro-4'
-Fluoro-5゛-propargyloxyphenyl)-5
-Isopropyl-1,3-oxazolidine-2,4-dione [Compound 18] (503+^g yield 52%) was obtained.

2-(N(2°, 4°-difluoro-
Potassium carbonate (150+9) was added to an acetonitrile solution (30 companies) of methyl 5'-propoxyphenyl)carbamoyloxy)lactate (635+ay, 2.0IIaol) and stirred at room temperature for 6 hours. After completion of the reaction, IN hydrochloric acid was added to the solution and ether was added. (50mZX3). I have lfi
After drying the layer and removing the solvent, the obtained oil was purified by silica gel column chromatography (eluent: chloroform/hexane 1/3) to obtain pure 3
-(2°,4'-difluoro-5'-propoxyphenyl)-5-methyl-1,3-oxazolidine-24-dione U compound 19] (320Ini?, yield 5.6
%) was obtained.

In the same manner as in Production Example 1, 2-fluoro-4
-2-+ prepared from chloro-5-proboxyphenylinthio-t and methyl 2-hydroxyisovalerate
N12°-Fluoro4°-chloro-5-propoxyphenyl)carbamoyloxy)methyl isovalerate (362
+ay, 1.01 uaol) in acetonitrile solution (3
Potassium carbonate (50n++) was added to the mixture and stirred at room temperature for 6 hours. By performing the same treatment as in Example 23, 3-(2″-fluoro4°-chloro-5′-
propoxyphenyl)-5isopropyl 1,3-oxazolidine-2,4dione (205+ny, yield 62%)
I got it.

3 (2°) using the same procedure as in Example 5
-Fluoro-4°-fluoro)-5'-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-
2,4-dione (650+++9.2.41mmo I
) and (th)-2-chloropropionitrile,
3-(<2°-fluoro-4'-fluoro)-5'-<
2 cyanethyl)oxyphenyl)-5-isopropyl-1,3-oxazolidine-2,4-dione [chemical 2
1] (380 rag, yield: 19%) was obtained.

3(
2°-chloro-4′-chloro)-5′-hydroxyphenyl)-5-isopropyl-1,3-oxazolidine-
2,4-dione (202+n, 0.67m5ol) (
±)-2-chloropropionitrile and 3((2°
-chloro-4゛-chloro)-5°-(2-cyanoethyl)oxyphenyl)-5-isopropyl 1,3-oxazolidine-2,4-dione [Monster 22] (114w+
y, yield 48%).

2-fluoro-4-chloro-5-isopropoxyphenylisocyanate (500B, 2.18 Tamol) and ethyl 2-hydroxyisovalerate <476 tag.

A small amount of propylene oxide and triethylamine (0,2
Jll') was added and stirred at room temperature for 2 hours. After the reaction was completed, the solution was washed three times with IN hydrochloric acid, and the organic layer was concentrated under reduced pressure at a dry time. The obtained pale brown oil was purified by silica gel column chromatography (eluent: ethyl acetate/hexane-1/l O) to obtain pure 2-
IN-<2'-fluoro-4'-chloro5°-iso10
Ethyl boxyphenyl)carbamoyloxy)isovalerate (550B, yield 67%) was obtained.

Sigandon 1 2-fluoro-4-chloro-5-cyclopentyloxyphenyl isocyanate (800 mg, 3.13 o
Add a small amount of propylene oxide and triethylamine (0.2ml) to the ether (301) i8 solution of f) and ethyl 2-hydroxy-3-methyl-3-butenoate (679 + y, 4.71 + poultry tool) at room temperature. Stirred for 2 hours. After the reaction was completed, the solution was washed three times with IN hydrochloric acid, and after drying the organic layer, 141i! Shita. The obtained pale brown oil was subjected to silica gel column chromatography (eluent:
Pure 2-(N-(2°-fluoro4'-chloro-5'-cyclopentyloxyphenyl ) Carbamoyloxy)
Ethyl-3-methyl-3-butenoate (1,01y, yield 81%) was obtained. Next, ethanol (30ml)
) A catalytic amount of 10% Pd/C (100+5fI) was added to the solution, and the reaction was allowed to proceed at room temperature under a hydrogen atmosphere at normal pressure until absorption of hydrogen gas ceased.

After the reaction, the catalyst was separated from P and the P solution was concentrated under reduced pressure to obtain a colorless and transparent oil. Next, recrystallization from methanol yielded the desired 2-+N-(2'-fluoro-4゛-Chloro-5°-cyclopentyloxyphenyl)carbamoyloxy)ethyl isovalerate<730
mg, yield 72%).

11 Shinyo 2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl isocyanate (25g102 mmol
) and ethyl 2-hydroxyisovalerate (22,4L l
Propylene oxide (3xl) and triethylamine <2
01e) was added and stirred at room temperature for 3 hours. After the reaction was completed, the solution was washed three times with IN hydrochloric acid, and the organic layer was dried and concentrated under reduced pressure. The obtained oil was chromatographed on silica gel and chromatographed (eluent, ethyl acetate/hexane-1).
/3) to obtain 2(N-(2'-fluoro-1°-chloro-5°-methquinecarbonyloxyphenyl)carbamoyloxy)yne ethyl valerate (2
4.5 g, yield 61%) was obtained. MP Near: 9 to 81°C The thus obtained compound of the present invention has excellent performance as an active ingredient of a herbicide, as described above.

When using the compound of the present invention as a herbicide, it can be used as it is, but it can be used as a herbicide by mixing one or several kinds of auxiliary agents with -m. usually,
As adjuvants, various single substances, extenders, solvents, surfactants,
Distributing stabilizers etc. and using conventional methods, such as hydrating agents,? It is preferable to use the preparation in the form of L preparation, powder, granule, etc.

Examples of solvents that are one of the adjuvants in herbicides containing the compound of the present invention as an active ingredient include water, alcohols, ketones, ethers, aliphatic and aromatic carbons, arsenic compounds, and halogenated hydrocarbons. , acid amides, Nisdels, nitriles, etc., and one or a mixture of two or more of these may be used. In addition, as fillers, clays such as kaolin and bentonite, talcs such as talc and pyrophyllite, mineral powders such as oxides such as diatoms and white carbon, soybean powder, and physical powders such as CMC are used. used. Surfactants may also be used as spreading agents, dispersants, emulsifiers, and penetrants.

Examples of the surfactant include nonionic surfactants, cationic surfactants, and amphoteric surfactants. These surfactants are used singly or as a mixture of two or more depending on the purpose.

Preferred methods of using the herbicide containing the herbicide of the present invention as an active ingredient include soil treatment, water surface treatment, foliage treatment, etc.
It can be applied to control weeds before they germinate or when they are young, giving a particularly effective effect.

Furthermore, the herbicide containing the herbicide of the present invention as an active ingredient may contain other active ingredients that do not inhibit the herbicidal activity of the active ingredient.
For example, it is also possible to mix or use other herbicides, insecticides, fungicides, plant growth regulators, and the like.

Next, the present invention will be explained in more detail by giving formulation examples of herbicides containing the present herbicide as an active ingredient, and test examples of the herbicidal effects of the present herbicides. Note that parts indicate parts by weight.

1st place RLJI! 20 parts of In compound, 35 parts of xylene, 40 parts of cyclohexanone, and 5 parts of Trupol 900A (Toho Kagaku ¥J) were uniformly mixed to obtain an emulsion. Emulsions were obtained using the same method for each of compounds 213.16-20.

A mixture of 50 parts of kidney embryo iuI, 25 parts of diatomaceous earth, 22 parts of clay, and 3 parts of Lunox R100C (manufactured by Toho Chemical) was evenly mixed and ground. A predetermined amount of water was added to the wheat to obtain a hydrating powder.

Wettable powders were obtained in the same manner for each of Compounds 2-13 and 16-20.

Nezumi LΣmouth Rainbow Rule 1 (A mixture of 5 parts of Hikimono 1, 35 parts of bentonite, 55 parts of talc, and 5 parts of sodium lignin sulfonate was uniformly mixed and ground, then water was added and kneaded. The granules were made into granules using an extrusion granulator, dried at 92°C, sized and made into 100ml granules.18x 1x2x
-13.16-20 were also obtained in the same manner to obtain granules.

■Water: Pack paddy soil into a Wagner bonoto with a size of 1/5,000 are, and sow or transplant seeds of Japanese barnyard grass, Japanese grasshopper, and Japanese grasshopper, as well as rice seedlings (variety: Nipponbare) at the 2- to 3-leaf stage and keep them moist. kept in condition. Five days later, the fish entered the water to a depth of 4 cm.

Thereafter, the water surface was treated with a predetermined amount of diluent so that the compound of the present invention was made into a wettable powder or emulsion according to the formulation example, and the amount was 20.10.5 grams per area. On the 20th day after treatment, the herbicidal effect on the test plants and the chemical damage to rice were confirmed.
), an investigation was conducted using the following criteria, and the results shown in Table 4 were obtained.

In addition, the herbicidal activity of the grain control products was investigated using the same criteria, and the results are also shown in Table 4, Effects on Paddy Weeds.

Table 4: Effect on paddy field weeds (continued) Effect on 1st surface water Ill'Bl grass (continued) Area 16:<
Fill a vat of 11c + 2, depth 7c + e with field soil,
9 days after sowing seeds of crabgrass, whiteberry, goldeneye, and soybean and covering the seeds with 1 cm of soil, 20.10.5 grams of the present invention made into a wettable powder or emulsion according to the formulation example was applied per are. A predetermined amount of the diluted solution was evenly spread over the soil covering. On the f&20th day of treatment, the sparrowcidal effect on Hongzu weeds and the chemical damage to soybeans were investigated in the same manner as in Test Example 1. The results are shown in Table 5.

Table 4: Effects on paddy field weeds (continued) Table 5: Effects of field soil treatment Table 5: Effects of field soil treatment (continued) Table 5: Effects of field soil treatment (continued) 1/5000 are Wagnerbot Fill the field with soil and add corn, cilantro, Japanese knotweed,
20 days after sowing weeds such as dogweed? Each test sample f formulated in the emulsion shown in Formulation Example 1 was applied to the stems and leaves of plants grown in the flame.
A chemical solution of a predetermined concentration obtained by diluting a compound with water is added to 1001/
The test plants were uniformly sprayed at an application rate of 10a. On the 20th day after the treatment, the herbicidal effect and phytotoxicity were evaluated in the same manner as in Test Example 1. The results are shown in Table 6.

Table 5 Effects of field soil treatment (continued) Table 6 Effects of stem and leaf treatment Table 6 Effects of foliage treatment (continued) Table 6 Effects of stem and leaf treatment (continued)

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, R^1 is a hydrogen atom, an alkyl group, a cyanoalkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, or It represents a lower alkyloxylcarbonyl group, and R^2 represents an alkyl group or a cycloalkyl group. The above alkyl group, cycloalkyl group, aralkyl group, alkenyl group and alkynyl group may be substituted. X^1 and X^2 each independently represent a halogen atom. ] An oxazolidine derivative represented by. (2) 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (II) [In the formula, R^1 is a hydrogen atom, an alkyl group, a cyanoalkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group , or a lower alkyloxylcarbonyl group, and R^2 represents an alkyl group or a cycloalkyl group. The above alkyl group, cycloalkyl group, aralkyl group, alkenyl group, and alkynyl group may be substituted. R^3 represents a lower alkyl group. X^1 and X^2
independently represent halogen atoms. ] By reacting the carbamate ester shown under basic conditions, the general formula ▲mathematical formula, chemical formula, table, etc.▼(I) [In the formula, R^1, R^2, X^1, and X^2 represents the same meaning as above. 2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I') [In the formula, R^2 is an alkyl group or a cycloalkyl group, and R^4 is a lower It is an alkyl group. The above alkyl group and cycloalkyl group may be substituted, X^
1 and X^2 each independently represent a halogen atom. This compound is a compound in which R^1 in the general formula (I) is a lower alkyloxylcarbonyl group. ] By hydrolyzing the carbonate group of the oxazolidine derivative represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ ( I ″) [wherein, R^2, X^1 and This compound has the same meaning as R in the general formula (I) above.
This is a compound when ^1 is a hydrogen atom. ], and then combine this with the general formula R^1'-Y(III) [wherein R^1' is an alkyl group, a cyanoalkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, or The alkyl group, cycloalkyl group, aralkyl group, alkenyl group and alkynyl group representing the alkynyl group may be substituted. Y is a leaving group. ] There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼( I
″′) [wherein R^1', R^2, X^1, and X^2 represent the same meanings as above. This compound has the above general formula (I
) in which R^1 is neither a hydrogen atom nor a lower alkyloxylcarbonyl group. ] or 3) general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (IV) [In the formula, R^1 is a hydrogen atom, an alkyl group, a cyanoalkyl group, a cycloalkyl group, Represents an aralkyl group, alkenyl group, alkynyl group, or lower alkyloxylcarbonyl group. R^5 and R^6 can independently form a hydrogen atom, an alkyl group, or together R^5 and R^6 can form a polymethylene chain. The above alkyl group, cycloalkyl group, aralkyl group, alkenyl group and alkynyl group may be substituted, X^
1 and X^2 each independently represent a halogen atom. ] By hydrogenating the double bond of a 5-substituted methylideneoxazolidinedione derivative represented by 1, R^2, X^1 and X^2 have the same meanings as above. ] A method for producing a novel oxazolidine derivative.