CA1221380A - 2-halogenoacetanilides herbicides - Google Patents
2-halogenoacetanilides herbicidesInfo
- Publication number
- CA1221380A CA1221380A CA000373332A CA373332A CA1221380A CA 1221380 A CA1221380 A CA 1221380A CA 000373332 A CA000373332 A CA 000373332A CA 373332 A CA373332 A CA 373332A CA 1221380 A CA1221380 A CA 1221380A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- trifluoromethyl
- methyl
- chloroacetanilide
- ethyl
- 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
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- 238000000034 method Methods 0.000 claims abstract description 41
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- 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 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
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- 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 3
- 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 3
- 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 3
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- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
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- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 239000003350 kerosene Substances 0.000 description 1
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 231100000817 safety factor Toxicity 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 239000008247 solid mixture Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 238000009736 wetting Methods 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)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13371880A | 1980-03-25 | 1980-03-25 | |
| US133,718 | 1980-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1221380A true CA1221380A (fr) | 1987-05-05 |
Family
ID=22459986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000373332A Expired CA1221380A (fr) | 1980-03-25 | 1981-03-18 | 2-halogenoacetanilides herbicides |
Country Status (40)
| Country | Link |
|---|---|
| JP (1) | JPS56145260A (fr) |
| AR (1) | AR228451A1 (fr) |
| AT (1) | AT370279B (fr) |
| AU (1) | AU537092B2 (fr) |
| BE (1) | BE887997A (fr) |
| BG (1) | BG36192A3 (fr) |
| BR (1) | BR8101599A (fr) |
| CA (1) | CA1221380A (fr) |
| CH (1) | CH644586A5 (fr) |
| CS (1) | CS227326B2 (fr) |
| CY (1) | CY1278A (fr) |
| DD (1) | DD157295A5 (fr) |
| DE (1) | DE3110523C2 (fr) |
| DK (1) | DK157189C (fr) |
| EG (1) | EG15025A (fr) |
| FI (1) | FI73972C (fr) |
| FR (1) | FR2479204B1 (fr) |
| GB (1) | GB2072181B (fr) |
| GR (1) | GR66543B (fr) |
| HU (1) | HU189497B (fr) |
| IE (1) | IE51698B1 (fr) |
| IL (2) | IL62420A (fr) |
| IT (1) | IT1194040B (fr) |
| KE (1) | KE3480A (fr) |
| LU (1) | LU83232A1 (fr) |
| MA (1) | MA19103A1 (fr) |
| MW (1) | MW1181A1 (fr) |
| MX (1) | MX6765E (fr) |
| NL (1) | NL8101326A (fr) |
| NO (1) | NO151617C (fr) |
| NZ (1) | NZ196541A (fr) |
| OA (1) | OA06771A (fr) |
| PL (1) | PL125386B1 (fr) |
| PT (1) | PT72685B (fr) |
| RO (3) | RO85641B (fr) |
| SE (1) | SE462093B (fr) |
| SG (1) | SG86784G (fr) |
| TR (1) | TR20869A (fr) |
| ZA (2) | ZA828914B (fr) |
| ZW (1) | ZW6081A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA861043B (en) * | 1985-02-13 | 1987-01-28 | Monsanto Co | 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 (fr) * | 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 FI FI810834A patent/FI73972C/fi not_active IP Right Cessation
- 1981-03-18 DK DK120681A patent/DK157189C/da active
- 1981-03-18 MW MW11/81A patent/MW1181A1/xx unknown
- 1981-03-18 MA MA19309A patent/MA19103A1/fr unknown
- 1981-03-18 IL IL62420A patent/IL62420A/xx unknown
- 1981-03-18 ZA ZA828914A patent/ZA828914B/xx unknown
- 1981-03-18 CS CS811984A patent/CS227326B2/cs unknown
- 1981-03-18 DE DE3110523A patent/DE3110523C2/de not_active Expired
- 1981-03-18 GB GB8108383A patent/GB2072181B/en not_active Expired
- 1981-03-18 AR AR284653A patent/AR228451A1/es active
- 1981-03-18 RO RO110026A patent/RO85641B/ro unknown
- 1981-03-18 ZA ZA00811808A patent/ZA811808B/xx unknown
- 1981-03-18 SE SE8101736A patent/SE462093B/sv not_active IP Right Cessation
- 1981-03-18 CY CY1278A patent/CY1278A/xx unknown
- 1981-03-18 GR GR64439A patent/GR66543B/el unknown
- 1981-03-18 NO NO810927A patent/NO151617C/no unknown
- 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 OA OA57357A patent/OA06771A/fr unknown
- 1981-03-18 AT AT0125681A patent/AT370279B/de not_active IP Right Cessation
- 1981-03-18 EG EG144/81A patent/EG15025A/xx active
- 1981-03-18 RO RO81103729A patent/RO81727A/fr unknown
- 1981-03-18 TR TR20869A patent/TR20869A/xx unknown
- 1981-03-18 NZ NZ196541A patent/NZ196541A/en unknown
- 1981-03-18 RO RO110027A patent/RO85642B/ro unknown
- 1981-03-18 IE IE596/81A patent/IE51698B1/en unknown
- 1981-03-18 ZW ZW60/81A patent/ZW6081A1/xx unknown
- 1981-03-18 FR FR8105442A patent/FR2479204B1/fr not_active Expired
- 1981-03-18 CH CH185581A patent/CH644586A5/de not_active IP Right Cessation
- 1981-03-18 AU AU68490/81A patent/AU537092B2/en not_active Ceased
- 1981-03-18 IT IT20413/81A patent/IT1194040B/it active
- 1981-03-18 BE BE0/204164A patent/BE887997A/fr not_active IP Right Cessation
- 1981-03-18 PL PL1981230198A patent/PL125386B1/pl unknown
- 1981-03-18 JP JP3808481A patent/JPS56145260A/ja active Granted
- 1981-03-18 NL NL8101326A patent/NL8101326A/nl not_active Application Discontinuation
- 1981-03-18 IL IL62411A patent/IL62411A/xx unknown
- 1981-03-18 PT PT72685A patent/PT72685B/pt unknown
- 1981-03-18 LU LU83232A patent/LU83232A1/fr unknown
- 1981-03-18 MX MX819355U patent/MX6765E/es unknown
- 1981-03-18 DD DD81228415A patent/DD157295A5/de not_active IP Right Cessation
- 1981-03-18 CA CA000373332A patent/CA1221380A/fr not_active Expired
- 1981-03-18 BR BR8101599A patent/BR8101599A/pt 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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| MKEX | Expiry | ||
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