DD233372A5 - Verfahren zur herstellung von n-substituierten aminopropansulfonsaeure-derivaten - Google Patents
Verfahren zur herstellung von n-substituierten aminopropansulfonsaeure-derivaten Download PDFInfo
- Publication number
- DD233372A5 DD233372A5 DD85276517A DD27651785A DD233372A5 DD 233372 A5 DD233372 A5 DD 233372A5 DD 85276517 A DD85276517 A DD 85276517A DD 27651785 A DD27651785 A DD 27651785A DD 233372 A5 DD233372 A5 DD 233372A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- phenyl
- preparation
- amino
- propane
- Prior art date
Links
- -1 N-SUBSTITUTED AMINOPROPANSULFONIC ACID Chemical class 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 239000007858 starting material Substances 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- JLXDVWLXRBMSDS-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-propylacetamide Chemical compound CCCN(C(=O)CCl)C1=C(C)C=CC=C1C JLXDVWLXRBMSDS-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 239000013543 active substance Substances 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 27
- 229910052717 sulfur Inorganic materials 0.000 description 22
- 229910052801 chlorine Inorganic materials 0.000 description 21
- 238000011282 treatment Methods 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000003306 harvesting Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- JCFQYIHWBUNKNN-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-propylacetamide Chemical compound CCCN(C(=O)CCl)C1=C(C)C=CC=C1CC JCFQYIHWBUNKNN-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
- 238000009395 breeding Methods 0.000 description 5
- 230000001488 breeding effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 244000020551 Helianthus annuus Species 0.000 description 3
- 240000008415 Lactuca sativa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- RVNGEWZRYLAOGF-UHFFFAOYSA-N 3-(n-(2-chloroacetyl)-2-ethylanilino)propane-1-sulfonic acid Chemical compound CCC1=CC=CC=C1N(CCCS(O)(=O)=O)C(=O)CCl RVNGEWZRYLAOGF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 244000013123 dwarf bean Species 0.000 description 2
- 235000021331 green beans Nutrition 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- ZIRURAJAJIQZFG-UHFFFAOYSA-N 1-aminopropane-1-sulfonic acid Chemical class CCC(N)S(O)(=O)=O ZIRURAJAJIQZFG-UHFFFAOYSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- CNUAGZDNUCVEGZ-UHFFFAOYSA-N 2-ethyl-6-methyl-n-propylaniline Chemical compound CCCNC1=C(C)C=CC=C1CC CNUAGZDNUCVEGZ-UHFFFAOYSA-N 0.000 description 1
- HRECXDAXWNCBBP-UHFFFAOYSA-N 2-ethyl-n-propylaniline Chemical compound CCCNC1=CC=CC=C1CC HRECXDAXWNCBBP-UHFFFAOYSA-N 0.000 description 1
- GGHLXLVPNZMBQR-UHFFFAOYSA-N 3,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC(Cl)=C1 GGHLXLVPNZMBQR-UHFFFAOYSA-N 0.000 description 1
- YYLLHTCECJVDFD-UHFFFAOYSA-N 3,5-dimethyl-n-propylaniline Chemical compound CCCNC1=CC(C)=CC(C)=C1 YYLLHTCECJVDFD-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydroponics (AREA)
- Cultivation Of Plants (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU84448A HU193197B (en) | 1984-02-03 | 1984-02-03 | Preparatives regulating the growth of plants containing as reagent derivatives of n-substituated amin-prophansulphonic acid and process for production of the reagent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD233372A5 true DD233372A5 (de) | 1986-02-26 |
Family
ID=10949644
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85276517A DD233372A5 (de) | 1984-02-03 | 1985-02-01 | Verfahren zur herstellung von n-substituierten aminopropansulfonsaeure-derivaten |
| DD85272977A DD231277A5 (de) | 1984-02-03 | 1985-02-01 | Pflanzenwachstumsregulierende mittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85272977A DD231277A5 (de) | 1984-02-03 | 1985-02-01 | Pflanzenwachstumsregulierende mittel |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4588435A (es) |
| JP (1) | JPS60248655A (es) |
| AU (1) | AU571050B2 (es) |
| BE (1) | BE901612A (es) |
| BG (2) | BG43689A3 (es) |
| CH (1) | CH663612A5 (es) |
| CS (1) | CS259524B2 (es) |
| DD (2) | DD233372A5 (es) |
| DE (1) | DE3503684A1 (es) |
| DK (1) | DK48385A (es) |
| ES (1) | ES8605793A1 (es) |
| FI (1) | FI80257C (es) |
| FR (1) | FR2559148B1 (es) |
| GB (1) | GB2153822B (es) |
| GR (1) | GR850291B (es) |
| HU (1) | HU193197B (es) |
| IT (1) | IT1184310B (es) |
| NL (1) | NL8500276A (es) |
| NO (1) | NO160710C (es) |
| PH (1) | PH20214A (es) |
| PL (2) | PL145843B1 (es) |
| PT (1) | PT79921B (es) |
| SE (1) | SE8500451L (es) |
| SU (2) | SU1375126A3 (es) |
| YU (1) | YU15385A (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02274612A (ja) * | 1989-04-17 | 1990-11-08 | Sanden Corp | 自動車用空調装置の制御装置 |
| EP2654433B1 (en) | 2010-12-21 | 2017-08-30 | Bayer Cropscience LP | Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
| EP2755485A1 (en) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH155446A (de) * | 1931-06-18 | 1932-06-30 | Ig Farbenindustrie Ag | Verfahren zur Herstellung eines Netz-, Emulgier-, Egalisier-, Disglomerier- und Waschmittels. |
| US4046911A (en) * | 1974-04-02 | 1977-09-06 | Ciba-Geigy Corporation | N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal composition and methods |
| FR2457281A1 (fr) * | 1979-05-23 | 1980-12-19 | Meram Lab | Nouveaux derives de l'acide 3-aminopropanesulfonique ayant une activite membranaire renforcee |
| MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
| DE3123731A1 (de) * | 1981-06-15 | 1982-12-30 | Basf Ag, 6700 Ludwigshafen | Chloressigsaeurecyclohexylamide, ihre herstellung, ihre verwendung zur herbizidbekaempfung und mittel dafuer |
-
1984
- 1984-02-03 HU HU84448A patent/HU193197B/hu not_active IP Right Cessation
-
1985
- 1985-01-25 PH PH31769A patent/PH20214A/en unknown
- 1985-01-29 CH CH384/85A patent/CH663612A5/de not_active IP Right Cessation
- 1985-01-31 US US06/696,658 patent/US4588435A/en not_active Expired - Fee Related
- 1985-01-31 BE BE1/11181A patent/BE901612A/fr not_active IP Right Cessation
- 1985-02-01 BG BG068650A patent/BG43689A3/xx unknown
- 1985-02-01 SE SE8500451A patent/SE8500451L/ not_active Application Discontinuation
- 1985-02-01 DK DK48385A patent/DK48385A/da not_active Application Discontinuation
- 1985-02-01 GB GB08502543A patent/GB2153822B/en not_active Expired
- 1985-02-01 AU AU38283/85A patent/AU571050B2/en not_active Ceased
- 1985-02-01 ES ES540302A patent/ES8605793A1/es not_active Expired
- 1985-02-01 FR FR8501443A patent/FR2559148B1/fr not_active Expired
- 1985-02-01 YU YU00153/85A patent/YU15385A/xx unknown
- 1985-02-01 SU SU853848402A patent/SU1375126A3/ru active
- 1985-02-01 FI FI850426A patent/FI80257C/fi not_active IP Right Cessation
- 1985-02-01 IT IT19335/85A patent/IT1184310B/it active
- 1985-02-01 NO NO850386A patent/NO160710C/no unknown
- 1985-02-01 NL NL8500276A patent/NL8500276A/nl not_active Application Discontinuation
- 1985-02-01 BG BG076833A patent/BG45381A3/xx unknown
- 1985-02-01 PT PT79921A patent/PT79921B/pt unknown
- 1985-02-01 GR GR850291A patent/GR850291B/el unknown
- 1985-02-01 PL PL1985256017A patent/PL145843B1/pl unknown
- 1985-02-01 CS CS85702A patent/CS259524B2/cs unknown
- 1985-02-01 JP JP60016681A patent/JPS60248655A/ja active Pending
- 1985-02-01 DD DD85276517A patent/DD233372A5/de not_active IP Right Cessation
- 1985-02-01 PL PL1985251805A patent/PL139979B1/pl unknown
- 1985-02-01 DD DD85272977A patent/DD231277A5/de not_active IP Right Cessation
- 1985-02-04 DE DE19853503684 patent/DE3503684A1/de not_active Withdrawn
- 1985-06-13 SU SU853912655A patent/SU1505426A3/ru active
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