KR102642423B1 - 제초제성 화합물 - Google Patents

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Publication number

KR102642423B1

KR102642423B1 KR1020207022476A KR20207022476A KR102642423B1 KR 102642423 B1 KR102642423 B1 KR 102642423B1 KR 1020207022476 A KR1020207022476 A KR 1020207022476A KR 20207022476 A KR20207022476 A KR 20207022476A KR 102642423 B1 KR102642423 B1 KR 102642423B1

Authority

KR

South Korea

Prior art keywords

alkyl

compound

formula

phenyl

alkoxy

Prior art date

2018-01-09

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 title claims abstract description 180
• 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
• 239000000203 mixture Substances 0.000 claims abstract description 103
• 238000000034 method Methods 0.000 claims abstract description 22
• GXZLRCBECYMKCZ-UHFFFAOYSA-N 5-phenylpyridazine-3,4-dione Chemical class C1(=CC=CC=C1)C=1C(C(N=NC=1)=O)=O GXZLRCBECYMKCZ-UHFFFAOYSA-N 0.000 claims abstract description 4
• 230000008635 plant growth Effects 0.000 claims abstract description 3
• -1 C 2 -C 4 haloalkenyl Chemical group 0.000 claims description 131
• 239000001257 hydrogen Substances 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical class 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 238000009472 formulation Methods 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 239000004009 herbicide Substances 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 9
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
• 239000000575 pesticide Substances 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• 229910052717 sulfur Chemical group 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 3
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000005494 pyridonyl group Chemical group 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 230000012010 growth Effects 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 150000001204 N-oxides Chemical class 0.000 claims 10
• 241000196324 Embryophyta Species 0.000 abstract description 43
• 238000002360 preparation method Methods 0.000 abstract description 11
• TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 abstract description 5
• 244000038559 crop plants Species 0.000 abstract description 5
• 239000000543 intermediate Substances 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
• 239000003054 catalyst Substances 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• 239000002904 solvent Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
• 239000000243 solution Substances 0.000 description 25
• 239000002585 base Substances 0.000 description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• 235000019439 ethyl acetate Nutrition 0.000 description 20
• 239000012043 crude product Substances 0.000 description 18
• 238000011065 in-situ storage Methods 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 235000019441 ethanol Nutrition 0.000 description 14
• 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 14
• 125000001309 chloro group Chemical group Cl* 0.000 description 13
• 238000003818 flash chromatography Methods 0.000 description 13
• 238000002156 mixing Methods 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 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 12
• 239000004094 surface-active agent Substances 0.000 description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
• 229920002554 vinyl polymer Polymers 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• 150000002148 esters Chemical group 0.000 description 11
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 240000008042 Zea mays Species 0.000 description 8
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
• 235000005822 corn Nutrition 0.000 description 8
• 239000003480 eluent Substances 0.000 description 8
• 239000004530 micro-emulsion Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 241000894007 species Species 0.000 description 8
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
• LNVKXEWNSUCHRX-UHFFFAOYSA-N [5-(2-bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl] 2-methylpropanoate Chemical compound CC(C(=O)OC=1C(=NN(C(C=1C1=C(C(=CC=C1F)Cl)Br)=O)C)C)C LNVKXEWNSUCHRX-UHFFFAOYSA-N 0.000 description 7
• SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 7
• 239000004495 emulsifiable concentrate Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000007921 spray Substances 0.000 description 7
• 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 6
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 125000000623 heterocyclic group Chemical group 0.000 description 6
• NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
• 239000000080 wetting agent Substances 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 235000001465 calcium Nutrition 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• CVKBMWWNKUWISK-UHFFFAOYSA-L dichloromethane;dichloropalladium Chemical compound ClCCl.Cl[Pd]Cl CVKBMWWNKUWISK-UHFFFAOYSA-L 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 239000004546 suspension concentrate Substances 0.000 description 5
• 125000001544 thienyl group Chemical group 0.000 description 5
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-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
• 241001621841 Alopecurus myosuroides Species 0.000 description 4
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• 229920000742 Cotton Polymers 0.000 description 4
• 244000299507 Gossypium hirsutum Species 0.000 description 4
• 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 4
• 240000007218 Ipomoea hederacea Species 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• PNJXXXLANXKEAV-UHFFFAOYSA-N OC(=O)Cc1c(F)ccc(Cl)c1Br Chemical compound OC(=O)Cc1c(F)ccc(Cl)c1Br PNJXXXLANXKEAV-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
• 244000061457 Solanum nigrum Species 0.000 description 4
• 235000002594 Solanum nigrum Nutrition 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 239000000654 additive Substances 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 230000004071 biological effect Effects 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• DZNFQIYYEXFFGV-UHFFFAOYSA-M chloropalladium(1+) 2-phenylaniline tritert-butylphosphane Chemical compound [Pd+]Cl.CC(C)(C)P(C(C)(C)C)C(C)(C)C.NC1=CC=CC=C1C1=CC=CC=[C-]1 DZNFQIYYEXFFGV-UHFFFAOYSA-M 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• 239000004491 dispersible concentrate Substances 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 238000011156 evaluation Methods 0.000 description 4
• 239000000194 fatty acid Substances 0.000 description 4
• 229930195729 fatty acid Natural products 0.000 description 4
• 150000004665 fatty acids Chemical class 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000010353 genetic engineering Methods 0.000 description 4
• 125000004970 halomethyl group Chemical group 0.000 description 4
• 125000001072 heteroaryl group Chemical group 0.000 description 4
• 125000005647 linker group Chemical group 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 239000012041 precatalyst Substances 0.000 description 4
• 239000002994 raw material Substances 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 239000000377 silicon dioxide Substances 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• 235000017550 sodium carbonate Nutrition 0.000 description 4
• 239000002689 soil Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 239000003053 toxin Substances 0.000 description 4
• 231100000765 toxin Toxicity 0.000 description 4
• 108700012359 toxins Proteins 0.000 description 4
• 239000004562 water dispersible granule Substances 0.000 description 4
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