DD215535A5 - Verfahren zu herstellung von neuen dinitrophenolen - Google Patents
Verfahren zu herstellung von neuen dinitrophenolen Download PDFInfo
- Publication number
- DD215535A5 DD215535A5 DD84259849A DD25984984A DD215535A5 DD 215535 A5 DD215535 A5 DD 215535A5 DD 84259849 A DD84259849 A DD 84259849A DD 25984984 A DD25984984 A DD 25984984A DD 215535 A5 DD215535 A5 DD 215535A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- group
- deep
- trifluoromethyl
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- RLXKADBMLQPLDV-UHFFFAOYSA-N 2-chloro-1,5-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C(C(F)(F)F)=C1 RLXKADBMLQPLDV-UHFFFAOYSA-N 0.000 claims abstract description 5
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 230000004071 biological effect Effects 0.000 abstract description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- GPGNBSPUWGESET-UHFFFAOYSA-N 2,4-dinitro-6-(trifluoromethyl)phenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1C(F)(F)F GPGNBSPUWGESET-UHFFFAOYSA-N 0.000 description 10
- 240000008042 Zea mays Species 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011734 sodium Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 210000003763 chloroplast Anatomy 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 235000012735 amaranth Nutrition 0.000 description 3
- 239000004178 amaranth Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical group CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- QJQKPQISRLUNHD-UHFFFAOYSA-L disodium;2-methyl-4,6-dinitrophenol;methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O.CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QJQKPQISRLUNHD-UHFFFAOYSA-L 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- FXZGYEWQIGIFMC-UHFFFAOYSA-N 2,6-dinitro-4-(trifluoromethyl)phenol Chemical compound OC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O FXZGYEWQIGIFMC-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JSWPEXGHOFWWKT-UHFFFAOYSA-N cyclohexanone;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound O=C1CCCCC1.CC1=CC(=O)CC(C)(C)C1 JSWPEXGHOFWWKT-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 244000230030 foxtail bristlegrass Species 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000276 potassium ferrocyanide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- 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 |
|---|---|---|---|
| HU83362A HU190439B (en) | 1983-02-03 | 1983-02-03 | Herbicidal, akaricidal and plant growth regulating compsitions comprising 2-/trifluoromethyl/-4,6-dinitrophenol or its salts as active substance and process for preparing the active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD215535A5 true DD215535A5 (de) | 1984-11-14 |
Family
ID=10949254
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84259849A DD215535A5 (de) | 1983-02-03 | 1984-02-03 | Verfahren zu herstellung von neuen dinitrophenolen |
| DD84266211A DD231714A5 (de) | 1983-02-03 | 1984-08-13 | Pflanzenschutzmittel und verfahren zum bekaempfen von schaedlingen und unkraeutern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84266211A DD231714A5 (de) | 1983-02-03 | 1984-08-13 | Pflanzenschutzmittel und verfahren zum bekaempfen von schaedlingen und unkraeutern |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS6041639A (cs) |
| AT (1) | AT384422B (cs) |
| AU (1) | AU579090B2 (cs) |
| BR (1) | BR8400453A (cs) |
| CH (1) | CH658243A5 (cs) |
| CS (1) | CS257773B2 (cs) |
| DD (2) | DD215535A5 (cs) |
| DE (1) | DE3403437A1 (cs) |
| DK (1) | DK47384A (cs) |
| ES (1) | ES529614A0 (cs) |
| FR (1) | FR2540489B1 (cs) |
| GB (2) | GB8402445D0 (cs) |
| GR (1) | GR81696B (cs) |
| HU (1) | HU190439B (cs) |
| IT (1) | IT1173208B (cs) |
| PL (1) | PL137335B1 (cs) |
| RO (1) | RO88543A (cs) |
| YU (1) | YU19584A (cs) |
| ZA (1) | ZA84689B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6377834B1 (ja) * | 2017-12-24 | 2018-08-22 | Ｏａｔアグリオ株式会社 | ニトロフェノール化合物及び殺ダニ活性化合物を含有する相乗的殺ダニ剤組成物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2733682A1 (de) * | 1977-07-26 | 1979-02-08 | Bayer Ag | Verfahren zur herstellung von trifluormethylphenolen |
| JPS55139341A (en) * | 1979-04-18 | 1980-10-31 | Kumiai Chem Ind Co Ltd | Dinitrophenol derivative, its preparation, and agricultural and horticultural germicidal and herbicidal agent, containing it as effective component |
| DE3315798A1 (de) * | 1983-04-30 | 1984-10-31 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 6-chlor-2,4-dinitrophenol |
-
1983
- 1983-02-03 HU HU83362A patent/HU190439B/hu not_active IP Right Cessation
-
1984
- 1984-01-30 ZA ZA84689A patent/ZA84689B/xx unknown
- 1984-01-31 GB GB848402445A patent/GB8402445D0/en active Pending
- 1984-02-01 DE DE19843403437 patent/DE3403437A1/de not_active Withdrawn
- 1984-02-01 FR FR8401542A patent/FR2540489B1/fr not_active Expired
- 1984-02-02 BR BR8400453A patent/BR8400453A/pt unknown
- 1984-02-02 AU AU24094/84A patent/AU579090B2/en not_active Ceased
- 1984-02-02 IT IT19428/84A patent/IT1173208B/it active
- 1984-02-02 DK DK47384A patent/DK47384A/da not_active Application Discontinuation
- 1984-02-02 PL PL1984246022A patent/PL137335B1/pl unknown
- 1984-02-02 AT AT0033384A patent/AT384422B/de not_active IP Right Cessation
- 1984-02-02 GR GR73688A patent/GR81696B/el unknown
- 1984-02-03 ES ES529614A patent/ES529614A0/es active Granted
- 1984-02-03 JP JP59017226A patent/JPS6041639A/ja active Pending
- 1984-02-03 CS CS84801A patent/CS257773B2/cs unknown
- 1984-02-03 DD DD84259849A patent/DD215535A5/de not_active IP Right Cessation
- 1984-02-03 YU YU00195/84A patent/YU19584A/xx unknown
- 1984-02-03 GB GB08402952A patent/GB2135993B/en not_active Expired
- 1984-02-03 RO RO84113507A patent/RO88543A/ro unknown
- 1984-02-03 CH CH513/84A patent/CH658243A5/de not_active IP Right Cessation
- 1984-08-13 DD DD84266211A patent/DD231714A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK47384A (da) | 1984-08-04 |
| ATA33384A (de) | 1987-04-15 |
| YU19584A (en) | 1988-04-30 |
| IT1173208B (it) | 1987-06-18 |
| CS80184A2 (en) | 1987-11-12 |
| GB8402952D0 (en) | 1984-03-07 |
| HU190439B (en) | 1986-09-29 |
| DD231714A5 (de) | 1986-01-08 |
| FR2540489B1 (fr) | 1987-08-21 |
| GB2135993A (en) | 1984-09-12 |
| BR8400453A (pt) | 1984-09-11 |
| DE3403437A1 (de) | 1984-08-09 |
| IT8419428A0 (it) | 1984-02-02 |
| DK47384D0 (da) | 1984-02-02 |
| CS257773B2 (en) | 1988-06-15 |
| ES8506581A1 (es) | 1985-08-01 |
| GB8402445D0 (en) | 1984-03-07 |
| AT384422B (de) | 1987-11-10 |
| PL137335B1 (en) | 1986-05-31 |
| AU579090B2 (en) | 1988-11-17 |
| GR81696B (cs) | 1984-12-12 |
| RO88543A (ro) | 1986-02-28 |
| ZA84689B (en) | 1984-11-28 |
| CH658243A5 (de) | 1986-10-31 |
| AU2409484A (en) | 1984-08-09 |
| ES529614A0 (es) | 1985-08-01 |
| PL246022A1 (en) | 1985-01-30 |
| GB2135993B (en) | 1987-05-07 |
| HUT33948A (en) | 1985-01-28 |
| JPS6041639A (ja) | 1985-03-05 |
| FR2540489A1 (fr) | 1984-08-10 |
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