JPH0439466B2 - - Google Patents
Info
- Publication number
- JPH0439466B2 JPH0439466B2 JP15617983A JP15617983A JPH0439466B2 JP H0439466 B2 JPH0439466 B2 JP H0439466B2 JP 15617983 A JP15617983 A JP 15617983A JP 15617983 A JP15617983 A JP 15617983A JP H0439466 B2 JPH0439466 B2 JP H0439466B2
- Authority
- JP
- Japan
- Prior art keywords
- ethylenedioxy
- nitrophenol
- ethylenedioxynitrobenzene
- ethyl
- alkali metal
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- -1 ethylenedioxy-2-nitrophenol Chemical compound 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 4
- LRHFGBDYKMSVMK-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound O1CCOC2=C1C=C(O)C([N+]([O-])=O)=C2 LRHFGBDYKMSVMK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000219095 Vitis Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XDHJIJSXCHOQQI-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=C1C=CC=C2[N+](=O)[O-] XDHJIJSXCHOQQI-UHFFFAOYSA-N 0.000 description 1
- CHSUFMWHKPBFBY-UHFFFAOYSA-N 6-chloro-7-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=C1C=C([N+](=O)[O-])C(Cl)=C2 CHSUFMWHKPBFBY-UHFFFAOYSA-N 0.000 description 1
- MQSGCURTKWHBRX-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC([N+](=O)[O-])=CC=C21 MQSGCURTKWHBRX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- DSRXQXXHDIAVJT-UHFFFAOYSA-N acetonitrile;n,n-dimethylformamide Chemical compound CC#N.CN(C)C=O DSRXQXXHDIAVJT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617983A JPS6048984A (ja) | 1983-08-25 | 1983-08-25 | ４，５−エチレンジオキシ−２−ニトロフェノ−ルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617983A JPS6048984A (ja) | 1983-08-25 | 1983-08-25 | ４，５−エチレンジオキシ−２−ニトロフェノ−ルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6048984A JPS6048984A (ja) | 1985-03-16 |
| JPH0439466B2 true JPH0439466B2 (fr) | 1992-06-29 |
Family
ID=15622078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15617983A Granted JPS6048984A (ja) | 1983-08-25 | 1983-08-25 | ４，５−エチレンジオキシ−２−ニトロフェノ−ルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6048984A (fr) |
-
1983
- 1983-08-25 JP JP15617983A patent/JPS6048984A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6048984A (ja) | 1985-03-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4367336A (en) | 2-Substituted-5-trifluoromethylpyridines and process for producing the same | |
| AU618062B2 (en) | Method for the preparation of o-carboxyarylimidazolinones | |
| JPH0240664B2 (fr) | ||
| JPH0439466B2 (fr) | ||
| DE2033357C3 (de) | Palmitoyl-propandioKl 3)-phosphorsäure-S-trimethylaminophenylester und Verfahren zu dessen Herstellung | |
| JPH0446274B2 (fr) | ||
| JPH0362708B2 (fr) | ||
| JPH0463876B2 (fr) | ||
| US20230088326A1 (en) | Process for preparation of arthropodicidal anthranilamide compounds | |
| US4216008A (en) | Butenoic acid derivatives | |
| JPH0436146B2 (fr) | ||
| JPH0136818B2 (fr) | ||
| JPS6257194B2 (fr) | ||
| JPH01301668A (ja) | マンデル酸誘導体及び除草剤 | |
| JP2001322950A (ja) | ２−アルキレンアダマンタンの製造方法 | |
| JP2920557B2 (ja) | ２−（５−アミノ−２−クロロ−４−フルオロフエニルチオ）酢酸メチルエステルの製造法およびその中間体 | |
| JPH0439465B2 (fr) | ||
| JP2719604B2 (ja) | フッ素置換ピリジン誘導体 | |
| JPS6210500B2 (fr) | ||
| JPH0456B2 (fr) | ||
| JPH01168664A (ja) | シクロヘキセノン誘導体およびその製造法 | |
| JPS58144381A (ja) | β−ケトエステル誘導体及びその製造方法 | |
| JPH08193011A (ja) | 除草性スルホンアミド化合物 | |
| JP2606796B2 (ja) | 置換ピリジン系化合物の製造方法 | |
| JP4828740B2 (ja) | １，２，５−チアジアゾイルメタノン誘導体の製造方法及びジオキシム誘導体 |