JPWO2021170464A5 - - Google Patents

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Publication number

JPWO2021170464A5

JPWO2021170464A5 JP2022551250A JP2022551250A JPWO2021170464A5 JP WO2021170464 A5 JPWO2021170464 A5 JP WO2021170464A5 JP 2022551250 A JP2022551250 A JP 2022551250A JP 2022551250 A JP2022551250 A JP 2022551250A JP WO2021170464 A5 JPWO2021170464 A5 JP WO2021170464A5

Authority

JP

Japan

Prior art keywords

alkyl

hydrogen

alkoxy

cyano

cycloalkyl

Prior art date

2024-02-22

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 442
• 239000001257 hydrogen Substances 0.000 claims description 343
• 229910052739 hydrogen Inorganic materials 0.000 claims description 343
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 209
• 239000011737 fluorine Substances 0.000 claims description 177
• 229910052731 fluorine Inorganic materials 0.000 claims description 177
• -1 nitro, hydroxyl Chemical group 0.000 claims description 164
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 147
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 147
• 239000000460 chlorine Substances 0.000 claims description 146
• 229910052801 chlorine Inorganic materials 0.000 claims description 146
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 141
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 127
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 127
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 127
• 229910052794 bromium Inorganic materials 0.000 claims description 127
• 230000002363 herbicidal effect Effects 0.000 claims description 127
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 126
• 239000000203 mixture Substances 0.000 claims description 123
• 229910052736 halogen Inorganic materials 0.000 claims description 119
• 150000002367 halogens Chemical class 0.000 claims description 119
• 150000002431 hydrogen Chemical class 0.000 claims description 115
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 86
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 79
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 73
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
• 239000004009 herbicide Substances 0.000 claims description 56
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 53
• 238000009472 formulation Methods 0.000 claims description 49
• 125000004432 carbon atom Chemical group C* 0.000 claims description 46
• 229920006395 saturated elastomer Polymers 0.000 claims description 46
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 44
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 150000002148 esters Chemical class 0.000 claims description 39
• 238000000034 method Methods 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 33
• 125000001153 fluoro group Chemical group F* 0.000 claims description 30
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 28
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 27
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 24
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 24
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 23
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 21
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 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
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 11
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 11
• 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 10
• 150000001408 amides Chemical class 0.000 claims description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 7
• 150000007970 thio esters Chemical class 0.000 claims description 7
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
• 239000012752 auxiliary agent Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
• 241000196324 Embryophyta Species 0.000 description 52
• 239000000243 solution Substances 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 27
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 21
• 239000003112 inhibitor Substances 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 21
• 108090000623 proteins and genes Proteins 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• 239000003960 organic solvent Substances 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000013543 active substance Substances 0.000 description 18
• 244000038559 crop plants Species 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• BTTOSJPNLDNHSK-UHFFFAOYSA-N methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]furan-2-carboxylate Chemical compound COC(=O)C1=CC(NC(=O)OC(C)(C)C)=CO1 BTTOSJPNLDNHSK-UHFFFAOYSA-N 0.000 description 17
• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• 229910002091 carbon monoxide Inorganic materials 0.000 description 16
• 235000014113 dietary fatty acids Nutrition 0.000 description 16
• 239000000194 fatty acid Substances 0.000 description 16
• 229930195729 fatty acid Natural products 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• 108700019146 Transgenes Proteins 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 235000010469 Glycine max Nutrition 0.000 description 13
• 244000068988 Glycine max Species 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 239000000839 emulsion Substances 0.000 description 12
• 150000004665 fatty acids Chemical class 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 239000012043 crude product Substances 0.000 description 11
• 150000005690 diesters Chemical class 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 239000004094 surface-active agent Substances 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• 240000008042 Zea mays Species 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 229920000742 Cotton Polymers 0.000 description 9
• 241000219146 Gossypium Species 0.000 description 9
• 239000007821 HATU Substances 0.000 description 9
• 235000002595 Solanum tuberosum Nutrition 0.000 description 9
• 244000061456 Solanum tuberosum Species 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 239000007921 spray Substances 0.000 description 9
• 150000003871 sulfonates Chemical class 0.000 description 9
• 230000009261 transgenic effect Effects 0.000 description 9
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 8
• ONOZLMFKBURXKK-UHFFFAOYSA-N ClC=1C=C(NC(C(C(=O)OCC2=CC=CC=C2)OC)=O)C=C(C=1)Cl Chemical compound ClC=1C=C(NC(C(C(=O)OCC2=CC=CC=C2)OC)=O)C=C(C=1)Cl ONOZLMFKBURXKK-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
• 150000001735 carboxylic acids Chemical class 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000003086 colorant Substances 0.000 description 8
• 238000010790 dilution Methods 0.000 description 8
• 239000012895 dilution Substances 0.000 description 8
• 238000002703 mutagenesis Methods 0.000 description 8
• 231100000350 mutagenesis Toxicity 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 238000011282 treatment Methods 0.000 description 8
• 241000238631 Hexapoda Species 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Chemical class 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 7
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 239000000080 wetting agent Substances 0.000 description 7
• 235000003222 Helianthus annuus Nutrition 0.000 description 6
• 240000007594 Oryza sativa Species 0.000 description 6
• 235000007164 Oryza sativa Nutrition 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 240000006394 Sorghum bicolor Species 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
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
• 239000012267 brine Substances 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
• 239000002270 dispersing agent Substances 0.000 description 6
• 238000010410 dusting Methods 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 150000002500 ions Chemical class 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 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
• OVRPSWLZMQASRV-UHFFFAOYSA-N 2-fluoro-2,3-dimethoxy-3-oxopropanoic acid Chemical compound COC(=O)C(F)(OC)C(O)=O OVRPSWLZMQASRV-UHFFFAOYSA-N 0.000 description 5
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• PYQWBYOEFWTFPZ-UHFFFAOYSA-N ClC=1C=C(NC(C(C(=O)OC)(OC)F)=O)C=C(C=1)Cl Chemical compound ClC=1C=C(NC(C(C(=O)OC)(OC)F)=O)C=C(C=1)Cl PYQWBYOEFWTFPZ-UHFFFAOYSA-N 0.000 description 5
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• YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 description 5
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• RKEXKLRKXLRNMV-UHFFFAOYSA-N methyl 4-bromofuran-2-carboxylate Chemical compound COC(=O)C1=CC(Br)=CO1 RKEXKLRKXLRNMV-UHFFFAOYSA-N 0.000 description 5
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