JPWO2021170464A5

JPWO2021170464A5 -

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Publication number: JPWO2021170464A5
Authority: JP; Japan
Prior art keywords: alkyl; hydrogen; alkoxy; cyano; cycloalkyl
Prior art date: 2024-02-22
Legal status : Pending

Application number

JP2022551250A

Other languages

English (en)

Japanese (ja)

Other versions

JP2023514787A (ja

Publication date

2024-02-22

2021-02-17 Application filed filed Critical

2021-02-17 Priority claimed from PCT/EP2021/053846 external-priority patent/WO2021170464A1/en

2023-04-10 Publication of JP2023514787A publication Critical patent/JP2023514787A/ja

2024-02-22 Publication of JPWO2021170464A5 publication Critical patent/JPWO2021170464A5/ja

Status Pending legal-status Critical Current

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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
108010000700 Acetolactate synthase Proteins 0.000 description 5
244000105624 Arachis hypogaea Species 0.000 description 5
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
239000005562 Glyphosate Substances 0.000 description 5
244000020551 Helianthus annuus Species 0.000 description 5
YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 description 5
235000010749 Vicia faba Nutrition 0.000 description 5
240000006677 Vicia faba Species 0.000 description 5
230000009471 action Effects 0.000 description 5
239000002671 adjuvant Substances 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
230000006378 damage Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000008187 granular material Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
230000000749 insecticidal effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
RKEXKLRKXLRNMV-UHFFFAOYSA-N methyl 4-bromofuran-2-carboxylate Chemical compound COC(=O)C1=CC(Br)=CO1 RKEXKLRKXLRNMV-UHFFFAOYSA-N 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
239000012363 selectfluor Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
244000144725 Amygdalus communis Species 0.000 description 4
235000006008 Brassica napus var napus Nutrition 0.000 description 4
235000005979 Citrus limon Nutrition 0.000 description 4
244000131522 Citrus pyriformis Species 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
240000004658 Medicago sativa Species 0.000 description 4
235000002637 Nicotiana tabacum Nutrition 0.000 description 4
244000061176 Nicotiana tabacum Species 0.000 description 4
240000007817 Olea europaea Species 0.000 description 4
235000010617 Phaseolus lunatus Nutrition 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
239000004372 Polyvinyl alcohol Substances 0.000 description 4
240000000111 Saccharum officinarum Species 0.000 description 4
235000007201 Saccharum officinarum Nutrition 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
235000019714 Triticale Nutrition 0.000 description 4
235000007264 Triticum durum Nutrition 0.000 description 4
241000209143 Triticum turgidum subsp. durum Species 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
239000000969 carrier Substances 0.000 description 4
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239000011248 coating agent Substances 0.000 description 4
239000000084 colloidal system Substances 0.000 description 4
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MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
235000013399 edible fruits Nutrition 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
239000000499 gel Substances 0.000 description 4
238000010353 genetic engineering Methods 0.000 description 4
230000012010 growth Effects 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
235000009973 maize Nutrition 0.000 description 4
239000004530 micro-emulsion Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
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239000000047 product Substances 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
241000894007 species Species 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000004564 water dispersible powder for slurry treatment Substances 0.000 description 4
241000228158 x Triticosecale Species 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 3
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 3
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 3
XXQCWXBYAJLHJW-UHFFFAOYSA-N 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoic acid Chemical compound COC(C(O)=O)C(=O)NC1=CC(Cl)=CC(Cl)=C1 XXQCWXBYAJLHJW-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
235000011437 Amygdalus communis Nutrition 0.000 description 3
235000010777 Arachis hypogaea Nutrition 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
240000000385 Brassica napus var. napus Species 0.000 description 3
JNNPUHDRNWZBOE-UHFFFAOYSA-N C1=C(C=C(NC(=O)C(OC)(F)C(=O)O)C=C1Cl)Cl Chemical compound C1=C(C=C(NC(=O)C(OC)(F)C(=O)O)C=C1Cl)Cl JNNPUHDRNWZBOE-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
240000007154 Coffea arabica Species 0.000 description 3
235000007460 Coffea arabica Nutrition 0.000 description 3
239000005504 Dicamba Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005561 Glufosinate Substances 0.000 description 3
235000004341 Gossypium herbaceum Nutrition 0.000 description 3
240000002024 Gossypium herbaceum Species 0.000 description 3
240000007049 Juglans regia Species 0.000 description 3
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235000004431 Linum usitatissimum Nutrition 0.000 description 3
240000006240 Linum usitatissimum Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
235000003447 Pistacia vera Nutrition 0.000 description 3
240000006711 Pistacia vera Species 0.000 description 3
235000010582 Pisum sativum Nutrition 0.000 description 3
240000004713 Pisum sativum Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
235000007238 Secale cereale Nutrition 0.000 description 3
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JP2022551250A 2020-02-28 2021-02-17 マロンアミド除草剤 Pending JP2023514787A (ja)