DE2348487A1 - Neue substituierte crotonanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende zusammensetzungen - Google Patents
Neue substituierte crotonanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende zusammensetzungenInfo
- Publication number
- DE2348487A1 DE2348487A1 DE19732348487 DE2348487A DE2348487A1 DE 2348487 A1 DE2348487 A1 DE 2348487A1 DE 19732348487 DE19732348487 DE 19732348487 DE 2348487 A DE2348487 A DE 2348487A DE 2348487 A1 DE2348487 A1 DE 2348487A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- formula
- radical
- alkyl radical
- methoxycrotonamide
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 alkyl radical Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 12
- HFIOZQGCNMQTKS-HJWRWDBZSA-N (z)-3-methoxy-n-phenylbut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC=C1 HFIOZQGCNMQTKS-HJWRWDBZSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- KDPAUGYGDVPJLA-NTMALXAHSA-N (z)-3-methoxy-n-(3-methylphenyl)but-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC(C)=C1 KDPAUGYGDVPJLA-NTMALXAHSA-N 0.000 claims description 8
- 150000003931 anilides Chemical class 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- ALNLBVSCWBODNE-VURMDHGXSA-N (z)-3-methoxy-n-[3-(trifluoromethyl)phenyl]but-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC(C(F)(F)F)=C1 ALNLBVSCWBODNE-VURMDHGXSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
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- TXTRBYREKXCPKB-VURMDHGXSA-N (z)-n-(3-chlorophenyl)-3-methoxybut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=CC(Cl)=C1 TXTRBYREKXCPKB-VURMDHGXSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 244000025254 Cannabis sativa Species 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
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- 239000002244 precipitate Substances 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 7
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- 240000005979 Hordeum vulgare Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 241000219793 Trifolium Species 0.000 description 6
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- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 5
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- 239000000243 solution Substances 0.000 description 5
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- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
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- ZGCZHWUZVGIDCX-UHFFFAOYSA-N 3,3-dimethoxy-n-phenylhexanamide Chemical compound CCCC(OC)(OC)CC(=O)NC1=CC=CC=C1 ZGCZHWUZVGIDCX-UHFFFAOYSA-N 0.000 description 3
- HMNZRAXGYXHWLG-UHFFFAOYSA-N 3-methoxy-n-phenylhex-2-enamide Chemical compound CCCC(OC)=CC(=O)NC1=CC=CC=C1 HMNZRAXGYXHWLG-UHFFFAOYSA-N 0.000 description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- 239000005573 Linuron Substances 0.000 description 3
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- 229960001866 silicon dioxide Drugs 0.000 description 3
- CUNCJCGEVQJECQ-KTKRTIGZSA-N (z)-3-methoxy-2-methyl-n-phenylbut-2-enethioamide Chemical compound CO\C(C)=C(\C)C(=S)NC1=CC=CC=C1 CUNCJCGEVQJECQ-KTKRTIGZSA-N 0.000 description 2
- TXCFQDKGXCOKTA-SEYXRHQNSA-N (z)-3-phenoxy-n-phenylbut-2-enamide Chemical compound C=1C=CC=CC=1NC(=O)/C=C(/C)OC1=CC=CC=C1 TXCFQDKGXCOKTA-SEYXRHQNSA-N 0.000 description 2
- GICJFGGKRNLMBB-VURMDHGXSA-N (z)-n-(3,4-dichlorophenyl)-3-ethoxybut-2-enamide Chemical compound CCO\C(C)=C/C(=O)NC1=CC=C(Cl)C(Cl)=C1 GICJFGGKRNLMBB-VURMDHGXSA-N 0.000 description 2
- FOSFIXWZAJNJGQ-ALCCZGGFSA-N (z)-n-(3,4-dichlorophenyl)-3-methoxybut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1=CC=C(Cl)C(Cl)=C1 FOSFIXWZAJNJGQ-ALCCZGGFSA-N 0.000 description 2
- JOGAIDHEOAKDMN-UHFFFAOYSA-N 3,3-dimethoxy-n-phenylbutanamide Chemical compound COC(C)(OC)CC(=O)NC1=CC=CC=C1 JOGAIDHEOAKDMN-UHFFFAOYSA-N 0.000 description 2
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- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- A01N37/36—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/44—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7233960A FR2201035B1 (enrdf_load_stackoverflow) | 1972-09-26 | 1972-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2348487A1 true DE2348487A1 (de) | 1974-04-04 |
Family
ID=9104771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732348487 Withdrawn DE2348487A1 (de) | 1972-09-26 | 1973-09-26 | Neue substituierte crotonanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende zusammensetzungen |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2729672A1 (de) * | 1976-06-30 | 1978-01-12 | Kao Corp | Germicide herbicide fuer landwirtschaft und gartenbau |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2268010B1 (enrdf_load_stackoverflow) * | 1974-04-22 | 1976-10-29 | Roussel Uclaf |
-
1972
- 1972-09-26 FR FR7233960A patent/FR2201035B1/fr not_active Expired
-
1973
- 1973-08-21 DD DD173003A patent/DD112712A5/xx unknown
- 1973-08-26 IL IL43076A patent/IL43076A/xx unknown
- 1973-09-04 SE SE7312036A patent/SE408413B/xx unknown
- 1973-09-19 JP JP48105100A patent/JPS5811855B2/ja not_active Expired
- 1973-09-25 CA CA182,013A patent/CA1031789A/en not_active Expired
- 1973-09-25 SU SU731959057A patent/SU645556A3/ru active
- 1973-09-25 HU HURO752A patent/HU169385B/hu unknown
- 1973-09-25 ES ES419038A patent/ES419038A1/es not_active Expired
- 1973-09-25 CH CH1373673A patent/CH587010A5/xx not_active IP Right Cessation
- 1973-09-25 IT IT52745/73A patent/IT1047948B/it active
- 1973-09-25 BE BE136017A patent/BE805281A/xx unknown
- 1973-09-26 DE DE19732348487 patent/DE2348487A1/de not_active Withdrawn
- 1973-09-26 GB GB4511773A patent/GB1393319A/en not_active Expired
- 1973-09-26 NL NL7313245A patent/NL7313245A/xx not_active Application Discontinuation
-
1975
- 1975-08-07 SU SU752162199A patent/SU626675A3/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2729672A1 (de) * | 1976-06-30 | 1978-01-12 | Kao Corp | Germicide herbicide fuer landwirtschaft und gartenbau |
| DE2729672C2 (de) | 1976-06-30 | 1987-03-05 | Kao Soap Co., Ltd., Tokio/Tokyo | Germicide Herbicide für Landwirtschaft und Gartenbau |
Also Published As
| Publication number | Publication date |
|---|---|
| SE408413B (sv) | 1979-06-11 |
| JPS49100040A (enrdf_load_stackoverflow) | 1974-09-20 |
| DD112712A5 (de) | 1975-05-05 |
| BE805281A (fr) | 1974-03-25 |
| JPS5811855B2 (ja) | 1983-03-04 |
| IL43076A (en) | 1978-01-31 |
| FR2201035B1 (enrdf_load_stackoverflow) | 1980-04-25 |
| CH587010A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| IL43076A0 (en) | 1973-11-28 |
| HU169385B (enrdf_load_stackoverflow) | 1976-11-28 |
| ES419038A1 (es) | 1976-03-01 |
| FR2201035A1 (enrdf_load_stackoverflow) | 1974-04-26 |
| SU626675A3 (ru) | 1978-09-30 |
| NL7313245A (enrdf_load_stackoverflow) | 1974-03-28 |
| CA1031789A (en) | 1978-05-23 |
| GB1393319A (en) | 1975-05-07 |
| SU645556A3 (ru) | 1979-01-30 |
| IT1047948B (it) | 1980-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |