CA1058217A - Selective herbicidal phenylureas - Google Patents
Selective herbicidal phenylureasInfo
- Publication number
- CA1058217A CA1058217A CA205,683A CA205683A CA1058217A CA 1058217 A CA1058217 A CA 1058217A CA 205683 A CA205683 A CA 205683A CA 1058217 A CA1058217 A CA 1058217A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- dimethyl
- urea
- phenylureas
- phenyl
- 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
- 230000002363 herbicidal effect Effects 0.000 title abstract description 8
- 241000196324 Embryophyta Species 0.000 claims abstract description 22
- 229910052801 chlorine Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- -1 1,1-Dimethyl-3-(3-ethyl-4-chlorophenyl)-urea Chemical compound 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 4
- ZFBSFDYGZNPHEO-UHFFFAOYSA-N 3-(3-ethylphenyl)-1,1-dimethylurea Chemical compound CCC1=CC=CC(NC(=O)N(C)C)=C1 ZFBSFDYGZNPHEO-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 230000000885 phytotoxic effect Effects 0.000 claims description 2
- 231100000208 phytotoxic Toxicity 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000006378 damage Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 241000209504 Poaceae Species 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 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 3
- 239000000843 powder Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IVLLJZFRQMSRRX-UHFFFAOYSA-N 1-isocyanato-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(N=C=O)=C1 IVLLJZFRQMSRRX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QWZWEJVCSVTACA-UHFFFAOYSA-N 1,1-dimethyl-3-(3-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC(NC(=O)N(C)C)=C1 QWZWEJVCSVTACA-UHFFFAOYSA-N 0.000 description 1
- XCCNRBCNYGWTQX-UHFFFAOYSA-N 3-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(N)=C1 XCCNRBCNYGWTQX-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000004370 Pastinaca sativa Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1105173A CH575208A5 (enrdf_load_stackoverflow) | 1973-07-30 | 1973-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058217A true CA1058217A (en) | 1979-07-10 |
Family
ID=4369566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA205,683A Expired CA1058217A (en) | 1973-07-30 | 1974-07-26 | Selective herbicidal phenylureas |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5042036A (enrdf_load_stackoverflow) |
| CA (1) | CA1058217A (enrdf_load_stackoverflow) |
| CH (1) | CH575208A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2436108A1 (enrdf_load_stackoverflow) |
| ES (1) | ES428712A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2245623B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1473889A (enrdf_load_stackoverflow) |
| IL (1) | IL45269A (enrdf_load_stackoverflow) |
| ZA (1) | ZA744808B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110938019A (zh) * | 2019-12-10 | 2020-03-31 | 江苏快达农化股份有限公司 | 连续化合成异丙隆方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2739349C3 (de) * | 1977-09-01 | 1980-03-13 | Basf Ag, 6700 Ludwigshafen | N-O-Alkyl-phenyD-N'-methyl-N·methoxyharnstoffe und diese enthaltende Herbizide |
| DK1690853T3 (da) | 1999-01-13 | 2010-06-07 | Bayer Healthcare Llc | Omega-carboxyaryl-substituerede diphenylurinstoffer til anvendelse som raf-kinaseinhibitorer |
| US20020065296A1 (en) | 1999-01-13 | 2002-05-30 | Bayer Corporation | Heteroaryl ureas containing nitrogen hetero-atoms as p38 kinase inhibitors |
| AU2725000A (en) | 1999-01-13 | 2000-08-01 | Bayer Corporation | Omega-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| WO2007053574A2 (en) | 2005-10-31 | 2007-05-10 | Bayer Pharmaceuticals Corporation | Combinations comprising sorafenib and interferon for the treatment of cancer |
| CN102603573B (zh) * | 2012-02-15 | 2013-12-18 | 江苏快达农化股份有限公司 | 一种合成氟草隆原药的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL36220A0 (en) * | 1970-02-27 | 1971-04-28 | Ciba Geigy Ag | Use of a phenylurea for combating weeds in wheat,oats,rye,barley,rice and cotton |
-
1973
- 1973-07-30 CH CH1105173A patent/CH575208A5/xx not_active IP Right Cessation
-
1974
- 1974-07-15 IL IL45269A patent/IL45269A/xx unknown
- 1974-07-23 FR FR7425479A patent/FR2245623B1/fr not_active Expired
- 1974-07-26 CA CA205,683A patent/CA1058217A/en not_active Expired
- 1974-07-26 DE DE2436108A patent/DE2436108A1/de not_active Withdrawn
- 1974-07-29 ES ES428712A patent/ES428712A1/es not_active Expired
- 1974-07-29 GB GB3341174A patent/GB1473889A/en not_active Expired
- 1974-07-29 ZA ZA00744808A patent/ZA744808B/xx unknown
- 1974-07-30 JP JP49087446A patent/JPS5042036A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110938019A (zh) * | 2019-12-10 | 2020-03-31 | 江苏快达农化股份有限公司 | 连续化合成异丙隆方法 |
| CN110938019B (zh) * | 2019-12-10 | 2022-06-24 | 江苏快达农化股份有限公司 | 连续化合成异丙隆方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2245623B1 (enrdf_load_stackoverflow) | 1978-11-24 |
| CH575208A5 (enrdf_load_stackoverflow) | 1976-05-14 |
| DE2436108A1 (de) | 1975-02-13 |
| JPS5042036A (enrdf_load_stackoverflow) | 1975-04-16 |
| GB1473889A (en) | 1977-05-18 |
| ES428712A1 (es) | 1977-01-01 |
| FR2245623A1 (enrdf_load_stackoverflow) | 1975-04-25 |
| IL45269A (en) | 1978-01-31 |
| IL45269A0 (en) | 1974-10-22 |
| ZA744808B (en) | 1975-08-27 |
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