DE2407915A1 - Diphenylaetherverbindungen, verfahren zur herstellung derselben und herbicides mittel mit einem gehalt derselben - Google Patents
Diphenylaetherverbindungen, verfahren zur herstellung derselben und herbicides mittel mit einem gehalt derselbenInfo
- Publication number
- DE2407915A1 DE2407915A1 DE19742407915 DE2407915A DE2407915A1 DE 2407915 A1 DE2407915 A1 DE 2407915A1 DE 19742407915 DE19742407915 DE 19742407915 DE 2407915 A DE2407915 A DE 2407915A DE 2407915 A1 DE2407915 A1 DE 2407915A1
- Authority
- DE
- Germany
- Prior art keywords
- diphenyl ether
- trifluoromethyl
- compounds
- same
- dichloro
- 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.)
- Pending
Links
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 title claims description 25
- 239000004009 herbicide Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 22
- 230000002363 herbicidal effect Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 9
- 235000019713 millet Nutrition 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 241000287828 Gallus gallus Species 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010053759 Growth retardation Diseases 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- JDTMUJBWSGNMGR-UHFFFAOYSA-N 1-nitro-4-phenoxybenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 JDTMUJBWSGNMGR-UHFFFAOYSA-N 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 3
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 244000088415 Raphanus sativus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 240000008363 Stellaria alsine Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- FBKFIAIRSQOXJR-UHFFFAOYSA-N 1,2,3-trichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(Cl)=C1 FBKFIAIRSQOXJR-UHFFFAOYSA-N 0.000 description 2
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 2
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical compound COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 2
- 241001660456 Eleocharis tenuis Species 0.000 description 2
- 235000003990 Monochoria hastata Nutrition 0.000 description 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 244000155504 Rotala indica Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- -1 copper-I-oxide Chemical compound 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011707 mineral 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
- 239000004323 potassium nitrate Substances 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- 235000005474 African couch grass Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 101150039167 Bex3 gene Proteins 0.000 description 1
- 244000079471 Cardamine flexuosa Species 0.000 description 1
- 235000008477 Cardamine flexuosa Nutrition 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 244000283628 Elatine triandra Species 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 241001520106 Eustachys Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000064140 Lindernia Species 0.000 description 1
- 240000004428 Lindernia procumbens Species 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001577 potassium mineral Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1977873A JPS5248173B2 (https=) | 1973-02-20 | 1973-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2407915A1 true DE2407915A1 (de) | 1974-08-22 |
Family
ID=12008771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742407915 Pending DE2407915A1 (de) | 1973-02-20 | 1974-02-19 | Diphenylaetherverbindungen, verfahren zur herstellung derselben und herbicides mittel mit einem gehalt derselben |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5248173B2 (https=) |
| AU (1) | AU6558274A (https=) |
| BE (1) | BE811203A (https=) |
| BR (1) | BR7401218D0 (https=) |
| CA (1) | CA1020583A (https=) |
| DE (1) | DE2407915A1 (https=) |
| FR (1) | FR2218317B1 (https=) |
| GB (1) | GB1419209A (https=) |
| NL (1) | NL7402073A (https=) |
| SU (1) | SU559640A3 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001427A1 (de) * | 1977-10-06 | 1979-04-18 | Bayer Ag | 2,6-Dichlor-3'-fluor-4-trifluormethyl-6'-nitrodiphenyläther, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Entblätterungsmittel bei Baumwolle |
| EP0173349A1 (en) * | 1984-08-30 | 1986-03-05 | Occidental Chemical Corporation | Method for the preparation of nitrodiphenyl ethers |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6028219A (en) * | 1995-09-13 | 2000-02-22 | Zeneca Limited | Process for the nitration of diphenylethers |
| CN111138364A (zh) * | 2018-11-01 | 2020-05-12 | 东莞市东阳光菌阳氢专利农药有限公司 | 一种氟苯醚酰胺的制备方法 |
| CN111138300A (zh) * | 2018-11-02 | 2020-05-12 | 东莞市东阳光菌阳氢专利农药有限公司 | 一种氟苯醚酰胺及其中间体的制备方法 |
-
1973
- 1973-02-20 JP JP1977873A patent/JPS5248173B2/ja not_active Expired
-
1974
- 1974-02-14 GB GB678174A patent/GB1419209A/en not_active Expired
- 1974-02-14 AU AU65582/74A patent/AU6558274A/en not_active Expired
- 1974-02-15 NL NL7402073A patent/NL7402073A/xx not_active Application Discontinuation
- 1974-02-18 BE BE141068A patent/BE811203A/xx unknown
- 1974-02-19 DE DE19742407915 patent/DE2407915A1/de active Pending
- 1974-02-19 SU SU2001047A patent/SU559640A3/ru active
- 1974-02-19 BR BR121874A patent/BR7401218D0/pt unknown
- 1974-02-19 FR FR7405507A patent/FR2218317B1/fr not_active Expired
- 1974-02-20 CA CA193,058A patent/CA1020583A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001427A1 (de) * | 1977-10-06 | 1979-04-18 | Bayer Ag | 2,6-Dichlor-3'-fluor-4-trifluormethyl-6'-nitrodiphenyläther, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Entblätterungsmittel bei Baumwolle |
| EP0173349A1 (en) * | 1984-08-30 | 1986-03-05 | Occidental Chemical Corporation | Method for the preparation of nitrodiphenyl ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5248173B2 (https=) | 1977-12-08 |
| NL7402073A (https=) | 1974-08-22 |
| CA1020583A (en) | 1977-11-08 |
| BE811203A (fr) | 1974-06-17 |
| FR2218317B1 (https=) | 1978-09-15 |
| AU6558274A (en) | 1975-08-14 |
| BR7401218D0 (pt) | 1974-11-19 |
| GB1419209A (en) | 1975-12-24 |
| SU559640A3 (ru) | 1977-05-25 |
| JPS49108231A (https=) | 1974-10-15 |
| FR2218317A1 (https=) | 1974-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |