KR20210146968A - 살충 활성 디아진-아미드 화합물 - Google Patents

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Publication number

KR20210146968A

KR20210146968A KR1020217034551A KR20217034551A KR20210146968A KR 20210146968 A KR20210146968 A KR 20210146968A KR 1020217034551 A KR1020217034551 A KR 1020217034551A KR 20217034551 A KR20217034551 A KR 20217034551A KR 20210146968 A KR20210146968 A KR 20210146968A

Authority

KR

South Korea

Prior art keywords

formula

compounds

species

compound

spp

Prior art date

2019-03-29

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.)

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• 150000001875 compounds Chemical class 0.000 claims abstract description 491
• -1 stereoisomers Chemical class 0.000 claims abstract description 110
• 150000003839 salts Chemical class 0.000 claims abstract description 48
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 10
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
• 239000000203 mixture Substances 0.000 claims description 134
• 238000000034 method Methods 0.000 claims description 95
• 229910052739 hydrogen Inorganic materials 0.000 claims description 85
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 150000002367 halogens Chemical class 0.000 claims description 63
• 241000607479 Yersinia pestis Species 0.000 claims description 56
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 49
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
• 241001465754 Metazoa Species 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 239000004480 active ingredient Substances 0.000 claims description 26
• 241000238631 Hexapoda Species 0.000 claims description 23
• 241000244206 Nematoda Species 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 244000045947 parasite Species 0.000 claims description 18
• 230000000749 insecticidal effect Effects 0.000 claims description 16
• 241000238876 Acari Species 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 239000000463 material Substances 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000002671 adjuvant Substances 0.000 claims description 12
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 11
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 230000000895 acaricidal effect Effects 0.000 claims description 8
• 241000237852 Mollusca Species 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 3
• 239000000642 acaricide Substances 0.000 claims 1
• 239000002917 insecticide Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 257
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
• 241000894007 species Species 0.000 description 129
• 239000011541 reaction mixture Substances 0.000 description 108
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
• 239000000243 solution Substances 0.000 description 76
• 238000005481 NMR spectroscopy Methods 0.000 description 74
• 238000002360 preparation method Methods 0.000 description 74
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 71
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 66
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 49
• 239000000543 intermediate Substances 0.000 description 49
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
• 239000000741 silica gel Substances 0.000 description 44
• 229910002027 silica gel Inorganic materials 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 43
• 230000002829 reductive effect Effects 0.000 description 43
• 239000002904 solvent Substances 0.000 description 43
• 238000006243 chemical reaction Methods 0.000 description 42
• 241000196324 Embryophyta Species 0.000 description 41
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
• 229910052938 sodium sulfate Inorganic materials 0.000 description 40
• 235000011152 sodium sulphate Nutrition 0.000 description 40
• 238000003818 flash chromatography Methods 0.000 description 38
• 239000003053 toxin Substances 0.000 description 38
• 231100000765 toxin Toxicity 0.000 description 38
• 108700012359 toxins Proteins 0.000 description 38
• 239000000460 chlorine Substances 0.000 description 37
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
• 229910052794 bromium Inorganic materials 0.000 description 34
• 229910052786 argon Inorganic materials 0.000 description 33
• 239000002585 base Substances 0.000 description 33
• 150000001412 amines Chemical class 0.000 description 32
• 229910052801 chlorine Inorganic materials 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• 229910052740 iodine Inorganic materials 0.000 description 30
• 239000010410 layer Substances 0.000 description 30
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 description 29
• 239000000725 suspension Substances 0.000 description 29
• 239000013058 crude material Substances 0.000 description 27
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 26
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 240000008042 Zea mays Species 0.000 description 24
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 24
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 23
• 239000007787 solid Substances 0.000 description 23
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 22
• 238000009472 formulation Methods 0.000 description 22
• 239000003054 catalyst Substances 0.000 description 21
• 230000008569 process Effects 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 238000010438 heat treatment Methods 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 17
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
• 235000013311 vegetables Nutrition 0.000 description 16
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 238000001816 cooling Methods 0.000 description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 14
• 235000005822 corn Nutrition 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 230000014759 maintenance of location Effects 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 229910052763 palladium Inorganic materials 0.000 description 13
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 239000011630 iodine Substances 0.000 description 12
• 108090000623 proteins and genes Proteins 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
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• 238000003786 synthesis reaction Methods 0.000 description 12
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• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
• 241000254173 Coleoptera Species 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 239000012442 inert solvent Substances 0.000 description 11
• 229910000029 sodium carbonate Inorganic materials 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 241000255925 Diptera Species 0.000 description 10
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• 239000012267 brine Substances 0.000 description 10
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• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 235000011181 potassium carbonates Nutrition 0.000 description 10
• 102000004169 proteins and genes Human genes 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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• 229910000024 caesium carbonate Inorganic materials 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
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• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 150000001340 alkali metals Chemical class 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
• 229910052796 boron Inorganic materials 0.000 description 8
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• RTTTVBWZAQOVJU-UHFFFAOYSA-N 2-(1-cyanocyclopropyl)-6-(trifluoromethyl)pyridine-4-carboxylic acid Chemical compound C(#N)C1(CC1)C1=NC(=CC(=C1)C(=O)O)C(F)(F)F RTTTVBWZAQOVJU-UHFFFAOYSA-N 0.000 description 7
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• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 125000001153 fluoro group Chemical group F* 0.000 description 7
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• 239000000126 substance Substances 0.000 description 7
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• PXHHCCZONIYUTA-BYPYZUCNSA-N ClC=1C(=NC=CN=1)[C@H](C)N Chemical compound ClC=1C(=NC=CN=1)[C@H](C)N PXHHCCZONIYUTA-BYPYZUCNSA-N 0.000 description 6
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• OXNHVYXTLJNSCP-UHFFFAOYSA-N FC(OC=1C=NC(=NC=1)C=1C(=NC=CN=1)C(C)N)F Chemical compound FC(OC=1C=NC(=NC=1)C=1C(=NC=CN=1)C(C)N)F OXNHVYXTLJNSCP-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
• KWULFTQOKHWZSZ-UHFFFAOYSA-N NC(C)C=1C(=NC=CN=1)C1=CC=C(C=N1)C#N Chemical compound NC(C)C=1C(=NC=CN=1)C1=CC=C(C=N1)C#N KWULFTQOKHWZSZ-UHFFFAOYSA-N 0.000 description 6
• 241001674048 Phthiraptera Species 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 240000003768 Solanum lycopersicum Species 0.000 description 6
• 239000000654 additive Substances 0.000 description 6
• 150000001540 azides Chemical class 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 6
• 239000004009 herbicide Substances 0.000 description 6
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 6
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 239000011591 potassium Substances 0.000 description 6
• 229960003975 potassium Drugs 0.000 description 6
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
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