JPWO2021191035A5 - - Google Patents
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- Publication number
- JPWO2021191035A5 JPWO2021191035A5 JP2022557685A JP2022557685A JPWO2021191035A5 JP WO2021191035 A5 JPWO2021191035 A5 JP WO2021191035A5 JP 2022557685 A JP2022557685 A JP 2022557685A JP 2022557685 A JP2022557685 A JP 2022557685A JP WO2021191035 A5 JPWO2021191035 A5 JP WO2021191035A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- alkoxy
- cyano
- fluorine
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 378
- 239000001257 hydrogen Substances 0.000 claims description 274
- 229910052739 hydrogen Inorganic materials 0.000 claims description 274
- 239000011737 fluorine Substances 0.000 claims description 188
- 229910052731 fluorine Inorganic materials 0.000 claims description 188
- -1 nitro, hydroxyl Chemical group 0.000 claims description 163
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 158
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 156
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 155
- 239000000460 chlorine Substances 0.000 claims description 155
- 229910052801 chlorine Inorganic materials 0.000 claims description 154
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 144
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 132
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 132
- 229910052794 bromium Inorganic materials 0.000 claims description 132
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 124
- 229910052736 halogen Inorganic materials 0.000 claims description 95
- 150000002367 halogens Chemical class 0.000 claims description 95
- 150000002431 hydrogen Chemical class 0.000 claims description 92
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 91
- 230000002363 herbicidal effect Effects 0.000 claims description 81
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 76
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 70
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 68
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 239000004009 herbicide Substances 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 238000009472 formulation Methods 0.000 claims description 49
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 38
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 28
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 15
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 description 52
- 150000002148 esters Chemical class 0.000 description 38
- 150000003839 salts Chemical class 0.000 description 33
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- 239000003112 inhibitor Substances 0.000 description 21
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- 235000010469 Glycine max Nutrition 0.000 description 13
- 244000068988 Glycine max Species 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- 240000006394 Sorghum bicolor Species 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
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- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 5
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DE2059990A1 (de) * | 1970-12-05 | 1972-06-15 | Bayer Ag | Fungizide Mittel |
CZ244394A3 (en) * | 1993-10-08 | 1995-06-14 | Shell Int Research | Herbicidal 1,2,4-oxadiazolecarboxylic acids amides, esters or halides |
US5591695A (en) * | 1995-02-08 | 1997-01-07 | American Cyanamid Co. | Herbicidal [1,3,4]oxadiazoles and thiadiazoles |
EP0726263A3 (en) * | 1995-02-08 | 1996-10-09 | American Cyanamid Co | Herbicides (1,3,4) oxadiazoles and thiadiazoles |
MX2007002645A (es) | 2004-09-03 | 2007-04-27 | Syngenta Ltd | Derivados de isoxazolina y su uso como herbicidas. |
AU2005291117B2 (en) | 2004-10-05 | 2011-06-09 | Syngenta Limited | Isoxazoline derivatives and their use as herbicides |
GB0526044D0 (en) | 2005-12-21 | 2006-02-01 | Syngenta Ltd | Novel herbicides |
GB0603891D0 (en) | 2006-02-27 | 2006-04-05 | Syngenta Ltd | Novel herbicides |
EP2691379B1 (de) * | 2011-03-31 | 2016-11-02 | Bayer Intellectual Property GmbH | Herbizid und fungizid wirksame 3-phenylisoxazolin-5-carboxamide und 3- phenylisoxazolin-5-thioamide |
WO2014004882A2 (en) | 2012-06-30 | 2014-01-03 | Solarreserve, Llc | Position-encoded optical proxy for sensing and pointing of light sources |
JP6285937B2 (ja) * | 2012-09-25 | 2018-02-28 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 除草性および殺真菌性の5−オキシ置換3−フェニルイソオキサゾリン−5−カルボキサミドおよび5−オキシ置換3−フェニルイソオキサゾリン−5−チオアミド |
EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
RU2745802C2 (ru) | 2015-07-13 | 2021-04-01 | Фмк Корпорейшн | Арилоксипиримидиниловые эфиры в качестве гербицидов |
AU2018285212B2 (en) | 2017-06-13 | 2022-06-30 | Bayer Aktiengesellschaft | Herbicidally active 3-phenylisoxazoline-5-carboxamides of tetrahydro and dihydrofuran carboxylic acids and esters |
PL3638666T3 (pl) | 2017-06-13 | 2022-01-03 | Bayer Aktiengesellschaft | Chwastobójczo skuteczne 3-fenyloizoksazolino-5-karboksyamidy amidów kwasu tetrahydro- i dihydrofuranokarboksylowego |
BR112020003266A2 (pt) | 2017-08-17 | 2020-10-13 | Bayer Aktiengesellschaft | 3-fenil-5-trifluorometilisoxazolina-5-carboxamidas herbicidamente ativas de ésteres e ácidos ciclopentilcarboxílicos |
JP7217751B2 (ja) | 2018-01-25 | 2023-02-03 | バイエル・アクチエンゲゼルシヤフト | 除草活性を示すシクロペンテニルカルボン酸誘導体の3-フェニルイソオキサゾリン-5-カルボキサミド類 |
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