CS274252B2 - Agent for plants growth influencing and method of its active substance production - Google Patents
Agent for plants growth influencing and method of its active substance production Download PDFInfo
- Publication number
- CS274252B2 CS274252B2 CS244578A CS244578A CS274252B2 CS 274252 B2 CS274252 B2 CS 274252B2 CS 244578 A CS244578 A CS 244578A CS 244578 A CS244578 A CS 244578A CS 274252 B2 CS274252 B2 CS 274252B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- group
- active ingredient
- formula
- alkyl
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 12
- 230000012010 growth Effects 0.000 title description 18
- 239000013543 active substance Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- -1 nitrogen heterocyclic compounds Chemical class 0.000 claims abstract description 76
- 239000004480 active ingredient Substances 0.000 claims abstract description 44
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 230000008635 plant growth Effects 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 54
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- CEZMVTBHMCIRFC-UHFFFAOYSA-N n-[2,4-dichloro-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical group C1=C(Cl)C(NS(=O)(=O)C(F)(F)F)=CC(N2C(CCC2)=O)=C1Cl CEZMVTBHMCIRFC-UHFFFAOYSA-N 0.000 claims description 2
- ASRPAYCRIPRJQF-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxopiperidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CCCC1 ASRPAYCRIPRJQF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- KXZFSXQYGMQDQA-UHFFFAOYSA-N 1,1,1-trifluoro-n-(2-methyl-5-piperidin-1-ylphenyl)methanesulfonamide Chemical group C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC=C1N1CCCCC1 KXZFSXQYGMQDQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920001577 copolymer Chemical group 0.000 claims 1
- HAXKZIPFAYRRSP-UHFFFAOYSA-N n-[2,3-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical group FC(F)(F)S(=O)(=O)NC1=C(C)C(C)=CC(N2C(CCC2)=O)=C1 HAXKZIPFAYRRSP-UHFFFAOYSA-N 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 11
- 230000002363 herbicidal effect Effects 0.000 abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 57
- 241000196324 Embryophyta Species 0.000 description 43
- 239000000243 solution Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000001309 chloro group Chemical group Cl* 0.000 description 18
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 12
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229960001701 chloroform Drugs 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000209504 Poaceae Species 0.000 description 8
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- 230000000694 effects Effects 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 240000004296 Lolium perenne Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 5
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- 150000001768 cations Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
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- 230000035784 germination Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- SSXPQLXWKPOYLJ-UHFFFAOYSA-N 4,6-dichlorobenzene-1,3-diamine Chemical compound NC1=CC(N)=C(Cl)C=C1Cl SSXPQLXWKPOYLJ-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- 206010053759 Growth retardation Diseases 0.000 description 4
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- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 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 4
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- NQGLSXLJOHWQMF-UHFFFAOYSA-N n-[2,4-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=C(NS(=O)(=O)C(F)(F)F)C(C)=CC(C)=C1N1C(=O)CCC1 NQGLSXLJOHWQMF-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH470277A CH629076A5 (en) | 1977-04-15 | 1977-04-15 | Herbicidal and plant-growth-inhibiting compositions containing, as active substances, novel N-phenyl-substituted N-heterocycles, and their preparation and use |
| CH1366177A CH632131A5 (en) | 1977-11-09 | 1977-11-09 | Plant growth regulator, and process for the preparation of the novel N-phenyl-substituted N-heterocycles, which they contain as active substances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS244578A2 CS244578A2 (en) | 1990-09-12 |
| CS274252B2 true CS274252B2 (en) | 1991-04-11 |
Family
ID=25696101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS244578A CS274252B2 (en) | 1977-04-15 | 1978-04-14 | Agent for plants growth influencing and method of its active substance production |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US4208202A (da) |
| JP (1) | JPS53130652A (da) |
| AR (1) | AR231634A1 (da) |
| AT (1) | AT370280B (da) |
| AU (1) | AU520407B2 (da) |
| BR (1) | BR7802330A (da) |
| CA (1) | CA1102801A (da) |
| CS (1) | CS274252B2 (da) |
| DD (1) | DD137655A5 (da) |
| DE (1) | DE2815820A1 (da) |
| DK (1) | DK164678A (da) |
| ES (1) | ES468807A1 (da) |
| FR (1) | FR2387219B1 (da) |
| GB (1) | GB1593809A (da) |
| GR (1) | GR73529B (da) |
| HU (1) | HU185923B (da) |
| IL (1) | IL54501A (da) |
| IT (1) | IT1094916B (da) |
| NL (1) | NL7803885A (da) |
| PL (1) | PL111168B2 (da) |
| SE (1) | SE7804244L (da) |
| TR (1) | TR20413A (da) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387219B1 (da) * | 1977-04-15 | 1982-11-19 | Ciba Geigy Ag | |
| US4312663A (en) * | 1980-09-18 | 1982-01-26 | Minnesota Mining And Manufacturing Company | Cyclicacylaminoperfluoroalkanesulfonanilides and derivatives thereof |
| US4534786A (en) * | 1982-06-23 | 1985-08-13 | Chevron Research Company | 1-Alkyl derivatives of 3-aryloxy-4-(2-carbalkoxy)-phenyl-azet-2-ones as plant growth regulators |
| JPS6289651A (ja) * | 1985-06-11 | 1987-04-24 | Kumiai Chem Ind Co Ltd | トリフルオロメタンスルホンアニリド誘導体及びこれを含有する除草剤 |
| EP0338986B1 (de) * | 1988-04-19 | 1993-01-07 | Ciba-Geigy Ag | Pflanzenwuchshemmendes Mittel |
| US4956006A (en) * | 1988-12-27 | 1990-09-11 | Ici Americas Inc. | Substituted 1-phenyl pyrrolidones and their use as herbicides |
| EP0391847A1 (de) * | 1989-04-04 | 1990-10-10 | Ciba-Geigy Ag | 1-Phenyl-piperidin-2,4-dione mit herbizider Wirkung |
| US5223018A (en) * | 1989-04-04 | 1993-06-29 | Ciba-Geigy Corporation | 1-phenyl-piperdine-2,6-diones with herbicidal activity |
| US5278034A (en) * | 1990-04-27 | 1994-01-11 | Fuji Photo Film Co., Ltd. | Process for forming color image |
| DE10043790A1 (de) * | 2000-09-06 | 2002-03-14 | Bayer Ag | Substituierte 1-Aryl-pyridin-2-(thi)one |
| DE10139060A1 (de) * | 2001-08-08 | 2003-02-20 | Merck Patent Gmbh | Phenylderivate |
| JP2004107323A (ja) * | 2002-07-26 | 2004-04-08 | Nippon Nohyaku Co Ltd | 新規なハロアルキルスルホンアニリド誘導体及び除草剤並びにその使用方法 |
| AU2003252259A1 (en) * | 2002-07-26 | 2004-02-16 | Nihon Nohyaku Co., Ltd. | Novel haloalkylsulfonanilide derivatives, herbicides and usage thereof |
| US6818593B2 (en) * | 2003-03-24 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Production of 5-Methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with nitro compounds |
| US6855731B2 (en) * | 2003-03-24 | 2005-02-15 | E. I. Du Pont De Nemours And Company | Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with nitro compounds |
| EP2336104A4 (en) * | 2008-09-02 | 2012-01-25 | Nissan Chemical Ind Ltd | ORTHO-SUBSTITUTED HALOGENOALKYLSULFONANILIDE DERIVATIVE AND HERBICIDE |
| CN116888097A (zh) * | 2021-02-16 | 2023-10-13 | Fmc公司 | 卤代烷基磺酰苯胺基n-取代的除草环酰胺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1349517A (fr) * | 1962-01-09 | 1964-04-15 | Rohm & Haas | Composés herbicides à base de lactames |
| FR2387219B1 (da) * | 1977-04-15 | 1982-11-19 | Ciba Geigy Ag | |
| JPS5471550A (en) * | 1977-11-18 | 1979-06-08 | Hitachi Ltd | Base metal material for direct heating oxide cathode |
-
1978
- 1978-04-12 FR FR7810761A patent/FR2387219B1/fr not_active Expired
- 1978-04-12 DE DE19782815820 patent/DE2815820A1/de active Granted
- 1978-04-12 NL NL7803885A patent/NL7803885A/xx not_active Application Discontinuation
- 1978-04-12 US US05/896,970 patent/US4208202A/en not_active Expired - Lifetime
- 1978-04-13 CA CA301,079A patent/CA1102801A/en not_active Expired
- 1978-04-13 DD DD78204774A patent/DD137655A5/xx unknown
- 1978-04-13 AU AU35084/78A patent/AU520407B2/en not_active Expired
- 1978-04-13 AR AR271769D patent/AR231634A1/es active
- 1978-04-13 IL IL54501A patent/IL54501A/xx unknown
- 1978-04-14 CS CS244578A patent/CS274252B2/cs unknown
- 1978-04-14 GB GB14762/78A patent/GB1593809A/en not_active Expired
- 1978-04-14 SE SE7804244A patent/SE7804244L/xx unknown
- 1978-04-14 HU HU78CI1825A patent/HU185923B/hu unknown
- 1978-04-14 BR BR787802330A patent/BR7802330A/pt unknown
- 1978-04-14 TR TR20413A patent/TR20413A/xx unknown
- 1978-04-14 AT AT0264078A patent/AT370280B/de active
- 1978-04-14 DK DK164678A patent/DK164678A/da not_active IP Right Cessation
- 1978-04-14 IT IT22345/78A patent/IT1094916B/it active
- 1978-04-14 ES ES468807A patent/ES468807A1/es not_active Expired
- 1978-04-15 JP JP4473978A patent/JPS53130652A/ja active Granted
- 1978-04-15 PL PL1978206125A patent/PL111168B2/xx unknown
- 1978-04-15 GR GR55990A patent/GR73529B/el unknown
-
1980
- 1980-01-14 US US06/111,552 patent/US4294606A/en not_active Expired - Lifetime
-
1981
- 1981-10-26 US US06/314,620 patent/US4394156A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT7822345A0 (it) | 1978-04-14 |
| IL54501A0 (en) | 1978-07-31 |
| FR2387219B1 (da) | 1982-11-19 |
| AT370280B (de) | 1983-03-10 |
| ATA264078A (de) | 1982-08-15 |
| JPH0321545B2 (da) | 1991-03-22 |
| GR73529B (da) | 1984-03-12 |
| PL111168B2 (en) | 1980-08-30 |
| IT1094916B (it) | 1985-08-10 |
| PL206125A1 (pl) | 1979-06-04 |
| DD137655A5 (de) | 1979-09-19 |
| ES468807A1 (es) | 1979-12-16 |
| BR7802330A (pt) | 1979-02-13 |
| US4294606A (en) | 1981-10-13 |
| TR20413A (tr) | 1981-06-10 |
| AU520407B2 (en) | 1982-01-28 |
| DK164678A (da) | 1978-10-16 |
| CS244578A2 (en) | 1990-09-12 |
| GB1593809A (en) | 1981-07-22 |
| US4394156A (en) | 1983-07-19 |
| SE7804244L (sv) | 1978-10-16 |
| DE2815820C2 (da) | 1989-12-28 |
| JPS53130652A (en) | 1978-11-14 |
| IL54501A (en) | 1982-09-30 |
| NL7803885A (nl) | 1978-10-17 |
| HU185923B (en) | 1985-03-28 |
| US4208202A (en) | 1980-06-17 |
| CA1102801A (en) | 1981-06-09 |
| AU3508478A (en) | 1979-10-18 |
| DE2815820A1 (de) | 1978-10-26 |
| FR2387219A1 (da) | 1978-11-10 |
| AR231634A1 (es) | 1985-01-31 |
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