JPH0357098B2 - - Google Patents
Info
- Publication number
- JPH0357098B2 JPH0357098B2 JP15423189A JP15423189A JPH0357098B2 JP H0357098 B2 JPH0357098 B2 JP H0357098B2 JP 15423189 A JP15423189 A JP 15423189A JP 15423189 A JP15423189 A JP 15423189A JP H0357098 B2 JPH0357098 B2 JP H0357098B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- methyl
- carbonate
- sodium hydroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 14
- -1 2-(4-chloro-2-fluoro- 5-isopropoxyphenyl)-3,4,5,6 -tetrahydrophthalimide Chemical compound 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- UHVMWCUMBLQKKZ-UHFFFAOYSA-N (2-bromo-4-fluorophenyl) methyl carbonate Chemical compound COC(=O)OC1=CC=C(F)C=C1Br UHVMWCUMBLQKKZ-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DZLREMGDINSXSK-UHFFFAOYSA-N (2-chloro-4-fluoro-3-methylphenyl) hydrogen carbonate Chemical compound CC1=C(F)C=CC(OC(O)=O)=C1Cl DZLREMGDINSXSK-UHFFFAOYSA-N 0.000 description 1
- OYZZFKIAYSRYMD-UHFFFAOYSA-N (2-chloro-4-fluorophenyl) methyl carbonate Chemical compound COC(=O)OC1=CC=C(F)C=C1Cl OYZZFKIAYSRYMD-UHFFFAOYSA-N 0.000 description 1
- CCFNMXDJVOYPEY-UHFFFAOYSA-N 2-phenyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class O=C1C2CCC=CC2C(=O)N1C1=CC=CC=C1 CCFNMXDJVOYPEY-UHFFFAOYSA-N 0.000 description 1
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は一般式（）
〔式中、Ｘは塩素原子または臭素原子を表わ
す。〕
で示されるメチル ２−ハロ−４−フルオロフエ
ニル カルボナートに関するものである。
一般式（）で示される本発明化合物は、除草
作用を有する下記一般式（）で示される化合物
等の合成中間体として有用なものである。
〔式中、Ｒはアルキル基、アルケニル基または
アルキニル基を表わし、Ｘは前述と同じ意味を表
わす。〕
一般式（）で示される化合物は、トウモロコ
シ，コムギ，イネ，ダイズ，ワタ等の重要作用に
対して薬害が少なく、かつ雑草に対して強力な殺
草力を有するものであり、代表的な化合物とし
て、たとえば２−（４−クロロ−２−フルオロ−
５−イソプロポキシフエニル）−３，４，５，６
−テトラヒドロフタルイミド（第１表の化合物
１）、２−（４−クロロ−２−フルオロ−５−プロ
パルギルオキシフエニル）−３，４，５，６−テ
トラヒドロフタルイミド（第１表の化合物２）、
２−（４−クロロ−２−フルオロ−５−アリルオ
キシフエニル）−３，４，５，６−テトラヒドロ
フタルイミド（第１表の化合物３）があり、それ
らの除草活性は後述のとおりである。
The present invention is based on the general formula () [In the formula, X represents a chlorine atom or a bromine atom. ] This relates to methyl 2-halo-4-fluorophenyl carbonate represented by: The compound of the present invention represented by the general formula () is useful as a synthetic intermediate for the compound represented by the following general formula () having herbicidal activity. [In the formula, R represents an alkyl group, an alkenyl group, or an alkynyl group, and X represents the same meaning as above. ] The compound represented by the general formula () has little phytotoxicity against important effects on corn, wheat, rice, soybean, cotton, etc., and has strong herbicidal power against weeds, and is a typical As a compound, for example, 2-(4-chloro-2-fluoro-
5-isopropoxyphenyl)-3,4,5,6
-tetrahydrophthalimide (compound 1 in Table 1), 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (compound 2 in Table 1),
There is 2-(4-chloro-2-fluoro-5-allyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (compound 3 in Table 1), and their herbicidal activity is as described below. .
【表】
除草剤としての以下の試験例（参考例）におい
て、栽培植物に対する薬害と雑草に対する効力と
の評価はすべて以下に述べる基準にしたがい、０
から５までの整数による評価値で表わした。調査
時点に枯れ残つた植物体の地上部の生重量をはか
り、無処理区の植物体の生重量と比較したときの
比率（％）を計算する。栽培植物と雑草について
下表のような基準にもとづき、薬害と除草効果を
０から５までの数字で評価した。栽培植物に対す
る評価値０または１あるいは雑草に対する評価値
５または４は一般に妥当な栽培植物保護効果、あ
るいは雑草防除効果とみなされる。[Table] In the following test examples (reference examples) for herbicides, evaluations of phytotoxicity to cultivated plants and efficacy against weeds were all based on the criteria described below.
It is expressed as an evaluation value using an integer from to 5. The fresh weight of the above-ground parts of the plants that remained withered at the time of the survey was measured, and the ratio (%) when compared with the fresh weight of the plants in the untreated area was calculated. Cultivated plants and weeds were evaluated on a scale of 0 to 5 for chemical damage and herbicidal efficacy based on the criteria shown in the table below. An evaluation value of 0 or 1 for cultivated plants or an evaluation value of 5 or 4 for weeds is generally considered to be an appropriate cultivated plant protection effect or weed control effect.
【表】
参考例 トウモロコシ除草試験（茎葉処理）
縦35cm、横25cm、高さ10cmのプラスチツクトレ
ーに畑地土壌を詰め、トウモロコシ、イチビ、ヒ
マワリ、エビスグサ、マルバアサガオ、ノハラガ
ラシ、ハコベおよびエノコログサを播種し、温室
内で２週間育成したあと、縦50cm、横100cm、高
さ40cmの枠内にこのトレーを２個並べ、植物体の
上方から小型噴霧器で各薬剤の所定量を枠内全面
に茎葉処理した。薬剤散布後さらに８週間温室内
で育成したあと、各植物ごとに薬害あるいは除草
効力を調査した。その結果を第２表に示す。なお
処理薬剤は乳剤を使用し、展着剤を加えた水に乳
化させたものを供試した。薬剤処理時の植物の大
きさは種類によつて異なるが、ほぼ本葉１〜３葉
期で草丈２〜20cmであつた。[Table] Reference example: Corn weed control test (stem and foliage treatment) A plastic tray measuring 35 cm in length, 25 cm in width, and 10 cm in height was filled with field soil, and corn, Japanese radish, sunflower, Ebisu grass, Maruba morning glory, Wildflower, chickweed, and Japanese foxtail were sown. After growing in a greenhouse for two weeks, two of these trays were lined up in a frame measuring 50cm long, 100cm wide, and 40cm high, and a small sprayer was used from above the plant to apply a prescribed amount of each chemical to the entire area within the frame. . After being grown in a greenhouse for an additional 8 weeks after spraying, each plant was examined for chemical damage or herbicidal efficacy. The results are shown in Table 2. The processing agent used was an emulsion, which was emulsified in water to which a spreading agent was added. The size of the plants at the time of chemical treatment varied depending on the species, but they were approximately 2 to 20 cm tall at the 1 to 3 true leaf stage.
【表】【table】
【表】
一般式（）で示される除草剤として有用な化
合物は、一般式（）で示される本発明化合物よ
り下記の反応径路で合成することができる。
〔式中、ＸおよびＲは前述のとおりである。〕
すなわち、一般式（）のフエノール誘導体
は、ジメチルホルムアミド，ジメチルスルホキシ
ド等の溶媒中、炭酸カリウム等のアルカリ金属炭
酸塩、水酸化カリウム等のアルカリ金属水酸化
物、水酸化ナトルウム等のアルカリ金属水素化
物、ナトリウムアルコキシド等のアルカリ金属ア
ルコキシド等の塩基の存在下、好ましくはアルカ
リ金属炭酸塩の存在下、アルキルハライド、アル
ケニルハライド、アルキニルハライドと０〜100
℃、好ましくは70〜90℃で反応させることにより
一般式（）のＮ−フエニルテトラヒドロフタル
イミド誘導体に変換される。
一般式（）のフエノール誘導体は、一般式
（）のアミノフエノール誘導体と３，４，５，
６−テトラヒドロフタル酸無水物とを酢酸等の不
活性な溶媒中、１〜６時間、一般には２〜４時間
還流することにより製造できる。一般式（）の
アミノフエノール誘導体は、一般式（）のニト
ロフエノール誘導体を還元することにより得るこ
とができる。
芳香環のニトロ基の一般的な還元手段である接
触還元、鉄粉を用いた還元、硫化ナトリウムによ
る還元、硫黄化したNaBH4による還元等のいず
れの手段も可能であるが、二酸化白金を触媒と
し、エタノール溶媒下常温、常圧、水素による還
元が好ましい。この接触還元によつて得られた一
般式（）のアミノフエノール誘導体は、ほとん
ど精製することなしに３，４，５，６−テトラヒ
ドロフタル酸無水物との反応に使用できる。一般
式（）のニトロフエノール誘導体は、一般式
（）の本発明化合物を濃硫酸−濃硝酸を用いた
ニトロ化を常温で行ない、得られた一般式（）
のニトロフエノール誘導体を水酸化ナトリウム等
のアルカリ水溶液を用いて、好ましくは40〜80℃
で加水分解を行なうことにより得ることができ
る。
一般式（）の本発明化合物は、一般式（）
〔式中、Ｘは前述のとおりである。〕
で示されるハロフエノールを水酸化ナトリウム、
水酸化カリウム等の水溶液でアルカリ金属塩とし
た後、クロロ蟻酸メチルと水溶液中、好ましくは
０〜10℃で反応させることにより得ることができ
る。
尚、一般式（）のハロフエノールは、G.C.
Finger らJ.Am.Chem.Soc.81 94（1959）で公
知である。
実施例 １
メチル ２−クロロ−４−フルオロフエノール
カルボナートの合成。
２−クロロ−４−フルオロフエニル83.4gを水
酸化ナトリウム27.7gおよび水450mlより調整した
水酸化ナトリウム水溶液に加え、10℃以下でクロ
ロ蟻酸メチル69.2gを滴下した。生じた結晶を
別、水洗して134.8gの粗製のメチル ２−クロロ
−４−フルオロフエニル カルボナートを得た。
mp 69〜71℃
実施例 ２
メチル ２−ブロモ−４−フルオロフエニル
カルボナートの合成。
２−ブロモ−４−フルオロフエニル28gを水酸
化ナトリウム水溶液（水酸化ナトリウム7gを100
mlの水に溶解したもの）に加え、10℃以下でクロ
ロ蟻酸メチルを滴下し、生じた結晶は別、水洗
し、41gのメチル ２−ブロモ−４−フルオロフ
エニル カルボナートを得た。mp.80.7℃。[Table] A compound useful as a herbicide represented by the general formula () can be synthesized from the compound of the present invention represented by the general formula () by the following reaction route. [In the formula, X and R are as described above.] ] In other words, the phenol derivative of the general formula () can be used as an alkali metal carbonate such as potassium carbonate, an alkali metal hydroxide such as potassium hydroxide, or an alkali metal hydrogen such as sodium hydroxide in a solvent such as dimethylformamide or dimethyl sulfoxide. in the presence of a base such as an alkali metal alkoxide such as sodium alkoxide, preferably in the presence of an alkali metal carbonate, with an alkyl halide, alkenyl halide, or alkynyl halide of 0 to 100
It is converted into an N-phenyltetrahydrophthalimide derivative of the general formula () by reacting at a temperature of 70 to 90°C. The phenol derivative of general formula () is the aminophenol derivative of general formula () and 3,4,5,
It can be produced by refluxing 6-tetrahydrophthalic anhydride in an inert solvent such as acetic acid for 1 to 6 hours, generally 2 to 4 hours. The aminophenol derivative of general formula () can be obtained by reducing the nitrophenol derivative of general formula (). Any of the common methods for reducing the nitro group on the aromatic ring, such as catalytic reduction, reduction using iron powder, reduction with sodium sulfide, and reduction with sulfurized NaBH4 , is possible, but platinum dioxide as a catalyst Reduction with hydrogen in an ethanol solvent at room temperature and pressure is preferred. The aminophenol derivative of the general formula () obtained by this catalytic reduction can be used for reaction with 3,4,5,6-tetrahydrophthalic anhydride almost without purification. The nitrophenol derivative of the general formula () is obtained by nitrating the compound of the present invention of the general formula () using concentrated sulfuric acid and concentrated nitric acid at room temperature.
using an aqueous alkaline solution such as sodium hydroxide, preferably at 40 to 80°C.
It can be obtained by hydrolysis with The compound of the present invention of the general formula () is a compound of the general formula () [In the formula, X is as described above.] ] Halofenol shown by sodium hydroxide,
It can be obtained by making an alkali metal salt with an aqueous solution such as potassium hydroxide and then reacting it with methyl chloroformate in an aqueous solution, preferably at 0 to 10°C. In addition, halophenol in general formula () is GC
Finger et al. J. Am. Chem. Soc. 81 94 (1959). Example 1 Synthesis of methyl 2-chloro-4-fluorophenol carbonate. 83.4 g of 2-chloro-4-fluorophenyl was added to an aqueous sodium hydroxide solution prepared from 27.7 g of sodium hydroxide and 450 ml of water, and 69.2 g of methyl chloroformate was added dropwise at 10°C or lower. The resulting crystals were separated and washed with water to obtain 134.8 g of crude methyl 2-chloro-4-fluorophenyl carbonate.
mp 69-71℃ Example 2 Methyl 2-bromo-4-fluorophenyl
Carbonate synthesis. 28g of 2-bromo-4-fluorophenyl was dissolved in an aqueous solution of sodium hydroxide (7g of sodium hydroxide was dissolved in 100g of
ml of water), methyl chloroformate was added dropwise at below 10°C, and the resulting crystals were separated and washed with water to obtain 41 g of methyl 2-bromo-4-fluorophenyl carbonate. mp.80.7℃.
Claims (1)
す。〕 で示されるメチル ２−ハロ−４−フルオロフエ
ニル カルボナート。[Claims] 1. General formula [In the formula, X represents a chlorine atom or a bromine atom. ] Methyl 2-halo-4-fluorophenyl carbonate represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15423189A JPH0228139A (en) | 1989-06-15 | 1989-06-15 | Methyl 2-halo-4-fluorophenylcarbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15423189A JPH0228139A (en) | 1989-06-15 | 1989-06-15 | Methyl 2-halo-4-fluorophenylcarbonate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18202481A Division JPS5883652A (en) | 1981-03-30 | 1981-11-12 | 4-fluoro-5-nitrophenol derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0228139A JPH0228139A (en) | 1990-01-30 |
| JPH0357098B2 true JPH0357098B2 (en) | 1991-08-30 |
Family
ID=15579715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15423189A Granted JPH0228139A (en) | 1989-06-15 | 1989-06-15 | Methyl 2-halo-4-fluorophenylcarbonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0228139A (en) |
-
1989
- 1989-06-15 JP JP15423189A patent/JPH0228139A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0228139A (en) | 1990-01-30 |
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