JPH0148260B2 - - Google Patents
Info
- Publication number
- JPH0148260B2 JPH0148260B2 JP56038084A JP3808481A JPH0148260B2 JP H0148260 B2 JPH0148260 B2 JP H0148260B2 JP 56038084 A JP56038084 A JP 56038084A JP 3808481 A JP3808481 A JP 3808481A JP H0148260 B2 JPH0148260 B2 JP H0148260B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- compounds
- compound according
- chloroacetanilide
- methyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 118
- 230000002363 herbicidal effect Effects 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VJULAACBOCJUCR-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-ethyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(CC)C=CC=C1C(F)(F)F VJULAACBOCJUCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- VDSAJKLXUJHUHT-UHFFFAOYSA-N 2-chloro-N-[2-ethyl-6-(trifluoromethyl)phenyl]-N-(propan-2-yloxymethyl)acetamide Chemical compound C(C)(C)OCN(C1=C(C=CC=C1CC)C(F)(F)F)C(CCl)=O VDSAJKLXUJHUHT-UHFFFAOYSA-N 0.000 claims description 2
- YGJGEVWFKMHENL-UHFFFAOYSA-N 2-chloro-n-(2-methylpropoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC(C)COCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F YGJGEVWFKMHENL-UHFFFAOYSA-N 0.000 claims description 2
- KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 claims description 2
- FTHUAISISRFQDD-UHFFFAOYSA-N 2-chloro-n-[2-ethyl-6-(trifluoromethyl)phenyl]-n-(propoxymethyl)acetamide Chemical compound CCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1C(F)(F)F FTHUAISISRFQDD-UHFFFAOYSA-N 0.000 claims description 2
- SWBKUDOYZWYCPU-UHFFFAOYSA-N 2-chloro-n-[2-methyl-6-(trifluoromethyl)phenyl]-n-(propan-2-yloxymethyl)acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F SWBKUDOYZWYCPU-UHFFFAOYSA-N 0.000 claims description 2
- AURQSJHVURCBRX-UHFFFAOYSA-N 2-chloro-n-[2-methyl-6-(trifluoromethyl)phenyl]-n-(propoxymethyl)acetamide Chemical compound CCCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F AURQSJHVURCBRX-UHFFFAOYSA-N 0.000 claims description 2
- QUKFWAXIKVYCKS-UHFFFAOYSA-N 2-chloro-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=CC(C(F)(F)F)=C1NC(=O)CCl QUKFWAXIKVYCKS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- RUAQSKUPQZTMEK-UHFFFAOYSA-N 2-chloro-N-(2-methoxyethoxymethyl)-N-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound COCCOCN(C1=C(C=CC=C1C)C(F)(F)F)C(CCl)=O RUAQSKUPQZTMEK-UHFFFAOYSA-N 0.000 claims 1
- TUYICDQKMSJMRE-UHFFFAOYSA-N 2-chloro-n-(propan-2-yloxymethyl)-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound CC(C)OCN(C(=O)CCl)C1=CC=CC=C1C(F)(F)F TUYICDQKMSJMRE-UHFFFAOYSA-N 0.000 claims 1
- SOTIPGIUELTXMB-UHFFFAOYSA-N 2-chloro-n-[2-methyl-6-(trifluoromethyl)phenyl]-n-(prop-2-ynoxymethyl)acetamide Chemical compound CC1=CC=CC(C(F)(F)F)=C1N(COCC#C)C(=O)CCl SOTIPGIUELTXMB-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
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- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 3
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000237858 Gastropoda Species 0.000 description 3
- -1 However Chemical class 0.000 description 3
- 240000000486 Lepidium draba Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
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- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
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- STKYUBZNDSLORJ-UHFFFAOYSA-N 2-chloro-n-(2-ethoxyethyl)-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCCN(C(=O)CCl)C1=CC=CC=C1C(F)(F)F STKYUBZNDSLORJ-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder 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
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13371880A | 1980-03-25 | 1980-03-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56145260A JPS56145260A (en) | 1981-11-11 |
| JPH0148260B2 true JPH0148260B2 (es) | 1989-10-18 |
Family
ID=22459986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3808481A Granted JPS56145260A (en) | 1980-03-25 | 1981-03-18 | 2-haloacetanilide and its use |
Country Status (40)
| Country | Link |
|---|---|
| JP (1) | JPS56145260A (es) |
| AR (1) | AR228451A1 (es) |
| AT (1) | AT370279B (es) |
| AU (1) | AU537092B2 (es) |
| BE (1) | BE887997A (es) |
| BG (1) | BG36192A3 (es) |
| BR (1) | BR8101599A (es) |
| CA (1) | CA1221380A (es) |
| CH (1) | CH644586A5 (es) |
| CS (1) | CS227326B2 (es) |
| CY (1) | CY1278A (es) |
| DD (1) | DD157295A5 (es) |
| DE (1) | DE3110523C2 (es) |
| DK (1) | DK157189C (es) |
| EG (1) | EG15025A (es) |
| FI (1) | FI73972C (es) |
| FR (1) | FR2479204B1 (es) |
| GB (1) | GB2072181B (es) |
| GR (1) | GR66543B (es) |
| HU (1) | HU189497B (es) |
| IE (1) | IE51698B1 (es) |
| IL (2) | IL62420A (es) |
| IT (1) | IT1194040B (es) |
| KE (1) | KE3480A (es) |
| LU (1) | LU83232A1 (es) |
| MA (1) | MA19103A1 (es) |
| MW (1) | MW1181A1 (es) |
| MX (1) | MX6765E (es) |
| NL (1) | NL8101326A (es) |
| NO (1) | NO151617C (es) |
| NZ (1) | NZ196541A (es) |
| OA (1) | OA06771A (es) |
| PL (1) | PL125386B1 (es) |
| PT (1) | PT72685B (es) |
| RO (3) | RO85642B (es) |
| SE (1) | SE462093B (es) |
| SG (1) | SG86784G (es) |
| TR (1) | TR20869A (es) |
| ZA (2) | ZA828914B (es) |
| ZW (1) | ZW6081A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0192628A1 (en) * | 1985-02-13 | 1986-08-27 | Monsanto Company | Novel acetanilides and their use in the regulation of the natural growth or development of turf grass |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH579348A5 (es) * | 1973-02-08 | 1976-09-15 | Ciba Geigy Ag | |
| CH585191A5 (en) * | 1973-02-08 | 1977-02-28 | Ciba Geigy Ag | N-substd halogen acetanilide herbicides - prepd. from N-substd anilines and chloracetic anhydride or chloracetyl chloride |
| PL103793B1 (pl) * | 1976-03-19 | 1979-07-31 | Monsanto Co | Srodek chwastobojczy |
| DE2803662A1 (de) * | 1978-01-25 | 1979-07-26 | Schering Ag | Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| US4258196A (en) * | 1978-04-17 | 1981-03-24 | Monsanto Company | Process for the production of tertiary 2-haloacetamides |
-
1981
- 1981-03-18 RO RO110027A patent/RO85642B/ro unknown
- 1981-03-18 GB GB8108383A patent/GB2072181B/en not_active Expired
- 1981-03-18 CY CY1278A patent/CY1278A/xx unknown
- 1981-03-18 CS CS811984A patent/CS227326B2/cs unknown
- 1981-03-18 FR FR8105442A patent/FR2479204B1/fr not_active Expired
- 1981-03-18 IL IL62420A patent/IL62420A/xx unknown
- 1981-03-18 DD DD81228415A patent/DD157295A5/de not_active IP Right Cessation
- 1981-03-18 DK DK120681A patent/DK157189C/da active
- 1981-03-18 LU LU83232A patent/LU83232A1/fr unknown
- 1981-03-18 IL IL62411A patent/IL62411A/xx unknown
- 1981-03-18 EG EG144/81A patent/EG15025A/xx active
- 1981-03-18 PT PT72685A patent/PT72685B/pt unknown
- 1981-03-18 ZA ZA828914A patent/ZA828914B/xx unknown
- 1981-03-18 PL PL1981230198A patent/PL125386B1/pl unknown
- 1981-03-18 JP JP3808481A patent/JPS56145260A/ja active Granted
- 1981-03-18 RO RO110026A patent/RO85641B/ro unknown
- 1981-03-18 NZ NZ196541A patent/NZ196541A/en unknown
- 1981-03-18 AU AU68490/81A patent/AU537092B2/en not_active Ceased
- 1981-03-18 ZW ZW60/81A patent/ZW6081A1/xx unknown
- 1981-03-18 AT AT0125681A patent/AT370279B/de not_active IP Right Cessation
- 1981-03-18 NO NO810927A patent/NO151617C/no unknown
- 1981-03-18 ZA ZA00811808A patent/ZA811808B/xx unknown
- 1981-03-18 CA CA000373332A patent/CA1221380A/en not_active Expired
- 1981-03-18 IT IT20413/81A patent/IT1194040B/it active
- 1981-03-18 IE IE596/81A patent/IE51698B1/en unknown
- 1981-03-18 BR BR8101599A patent/BR8101599A/pt unknown
- 1981-03-18 OA OA57357A patent/OA06771A/xx unknown
- 1981-03-18 CH CH185581A patent/CH644586A5/de not_active IP Right Cessation
- 1981-03-18 RO RO81103729A patent/RO81727A/ro unknown
- 1981-03-18 TR TR20869A patent/TR20869A/xx unknown
- 1981-03-18 MW MW11/81A patent/MW1181A1/xx unknown
- 1981-03-18 AR AR284653A patent/AR228451A1/es active
- 1981-03-18 BE BE0/204164A patent/BE887997A/fr not_active IP Right Cessation
- 1981-03-18 NL NL8101326A patent/NL8101326A/nl not_active Application Discontinuation
- 1981-03-18 HU HU81693A patent/HU189497B/hu not_active IP Right Cessation
- 1981-03-18 BG BG8151267A patent/BG36192A3/xx unknown
- 1981-03-18 FI FI810834A patent/FI73972C/fi not_active IP Right Cessation
- 1981-03-18 SE SE8101736A patent/SE462093B/sv not_active IP Right Cessation
- 1981-03-18 MX MX819355U patent/MX6765E/es unknown
- 1981-03-18 GR GR64439A patent/GR66543B/el unknown
- 1981-03-18 DE DE3110523A patent/DE3110523C2/de not_active Expired
- 1981-03-18 MA MA19309A patent/MA19103A1/fr unknown
-
1984
- 1984-11-29 KE KE3480A patent/KE3480A/xx unknown
- 1984-12-04 SG SG867/84A patent/SG86784G/en unknown
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