TW202000026A - 殺有害生物活性之唑-醯胺化合物 - Google Patents

Info

Publication number

TW202000026A

TW202000026A TW108122879A TW108122879A TW202000026A TW 202000026 A TW202000026 A TW 202000026A TW 108122879 A TW108122879 A TW 108122879A TW 108122879 A TW108122879 A TW 108122879A TW 202000026 A TW202000026 A TW 202000026A

Authority

TW

Taiwan

Prior art keywords

compound

trifluoromethyl

spp

pyridine

methyl

Prior art date

2018-06-29

Links

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• RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 451
• -1 stereoisomers Chemical class 0.000 claims abstract description 143
• 150000003839 salts Chemical class 0.000 claims abstract description 52
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
• 238000000034 method Methods 0.000 claims description 173
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 140
• 239000000203 mixture Substances 0.000 claims description 110
• 229910052739 hydrogen Inorganic materials 0.000 claims description 84
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 150000002367 halogens Chemical group 0.000 claims description 56
• 241000196324 Embryophyta Species 0.000 claims description 46
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 45
• 241001465754 Metazoa Species 0.000 claims description 41
• 241000607479 Yersinia pestis Species 0.000 claims description 37
• 241000238631 Hexapoda Species 0.000 claims description 35
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 241000244206 Nematoda Species 0.000 claims description 30
• 239000004480 active ingredient Substances 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 25
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 20
• 241000238876 Acari Species 0.000 claims description 20
• 244000045947 parasite Species 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 18
• 230000000895 acaricidal effect Effects 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 230000000749 insecticidal effect Effects 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
• 239000000463 material Substances 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 238000006467 substitution reaction Methods 0.000 claims description 11
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 241000237852 Mollusca Species 0.000 claims description 6
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
• 241000282412 Homo Species 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 238000002405 diagnostic procedure Methods 0.000 claims description 2
• 230000002013 molluscicidal effect Effects 0.000 claims description 2
• 230000001069 nematicidal effect Effects 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 150000003222 pyridines Chemical group 0.000 claims 3
• 150000003230 pyrimidines Chemical group 0.000 claims 2
• 150000001350 alkyl halides Chemical class 0.000 claims 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
• 239000012752 auxiliary agent Substances 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 239000002917 insecticide Substances 0.000 abstract description 3
• 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 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 217
• 238000002360 preparation method Methods 0.000 description 115
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 92
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 91
• 239000011541 reaction mixture Substances 0.000 description 91
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• 235000019439 ethyl acetate Nutrition 0.000 description 73
• 238000005160 1H NMR spectroscopy Methods 0.000 description 70
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 47
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 43
• 239000003053 toxin Substances 0.000 description 40
• 231100000765 toxin Toxicity 0.000 description 40
• 108700012359 toxins Proteins 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• 239000011734 sodium Substances 0.000 description 36
• 239000000047 product Substances 0.000 description 34
• 239000012044 organic layer Substances 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• 241001124076 Aphididae Species 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 239000012074 organic phase Substances 0.000 description 29
• 238000010898 silica gel chromatography Methods 0.000 description 29
• 239000012267 brine Substances 0.000 description 28
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
• 239000003921 oil Substances 0.000 description 26
• 235000019198 oils Nutrition 0.000 description 26
• 239000007787 solid Substances 0.000 description 26
• 240000008042 Zea mays Species 0.000 description 24
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 24
• 239000012043 crude product Substances 0.000 description 24
• 230000002829 reductive effect Effects 0.000 description 24
• 229910052938 sodium sulfate Inorganic materials 0.000 description 24
• 235000011152 sodium sulphate Nutrition 0.000 description 24
• 229910052786 argon Inorganic materials 0.000 description 23
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• NSUQZJBDIRFKPY-UHFFFAOYSA-N 4-(1-cyanocyclopropyl)-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide Chemical compound C(#N)C1(CC1)C1=CC=C(C(=O)N(C(C)C=2N(N=CN=2)C2=NC=CC=N2)CC2CC2)C=C1 NSUQZJBDIRFKPY-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 21
• 235000005822 corn Nutrition 0.000 description 21
• 239000000725 suspension Substances 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 19
• 239000002585 base Substances 0.000 description 19
• 238000010438 heat treatment Methods 0.000 description 19
• 241001674048 Phthiraptera Species 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 241000894007 species Species 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 239000002671 adjuvant Substances 0.000 description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
• 241000578422 Graphosoma lineatum Species 0.000 description 16
• 239000002253 acid Substances 0.000 description 16
• 238000009835 boiling Methods 0.000 description 16
• 239000010410 layer Substances 0.000 description 15
• 229910052698 phosphorus Inorganic materials 0.000 description 15
• 239000011574 phosphorus Substances 0.000 description 15
• 108090000623 proteins and genes Proteins 0.000 description 15
• 235000013311 vegetables Nutrition 0.000 description 15
• 241000254173 Coleoptera Species 0.000 description 14
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
• 239000008346 aqueous phase Substances 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• 230000008569 process Effects 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 241001635274 Cydia pomonella Species 0.000 description 13
• 244000078703 ectoparasite Species 0.000 description 13
• 239000007788 liquid Substances 0.000 description 13
• 102000004169 proteins and genes Human genes 0.000 description 13
• 229920000742 Cotton Polymers 0.000 description 12
• 241000255925 Diptera Species 0.000 description 12
• 241000219146 Gossypium Species 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 12
• 229910000024 caesium carbonate Inorganic materials 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• RULDBWPJTJVTJJ-UHFFFAOYSA-N 3-[cyclopropyl(difluoro)methyl]-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide Chemical compound C1(CC1)C(C=1C=C(C(=O)N(C(C)C=2N(N=CN=2)C2=NC=CC=N2)CC2CC2)C=C(C=1)C(F)(F)F)(F)F RULDBWPJTJVTJJ-UHFFFAOYSA-N 0.000 description 11
• ITISFGMSEMUAQD-UHFFFAOYSA-N 6-(2-cyanopropan-2-yl)-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-4-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C(#N)C(C)(C)C1=CC(=CC(=N1)C(=O)N(C(C)C=1N(N=CN=1)C1=NC=CC=N1)CC1CC1)C(F)(F)F ITISFGMSEMUAQD-UHFFFAOYSA-N 0.000 description 11
• 241001124134 Chrysomelidae Species 0.000 description 11
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• ZYHSXFQPVDIXHD-UHFFFAOYSA-N N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-3-(trifluoromethyl)-5-[2-(trifluoromethyl)cyclopropyl]benzamide Chemical compound CC(NC(=O)C1=CC(=CC(=C1)C1CC1C(F)(F)F)C(F)(F)F)C1=NC=NN1C1=NC=CC=N1 ZYHSXFQPVDIXHD-UHFFFAOYSA-N 0.000 description 11
• 241001074088 Urophycis Species 0.000 description 11
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• 150000001408 amides Chemical class 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
• 230000009261 transgenic effect Effects 0.000 description 11
• 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 10
• 241000255777 Lepidoptera Species 0.000 description 10
• 241000500437 Plutella xylostella Species 0.000 description 10
• 235000002595 Solanum tuberosum Nutrition 0.000 description 10
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• 241001414989 Thysanoptera Species 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000007789 gas Substances 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 235000011181 potassium carbonates Nutrition 0.000 description 10
• 229910000029 sodium carbonate Inorganic materials 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• 241000220225 Malus Species 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 241001481703 Rhipicephalus <genus> Species 0.000 description 9
• 150000001340 alkali metals Chemical class 0.000 description 9
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• 125000004093 cyano group Chemical group *C#N 0.000 description 9
• 238000011161 development Methods 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• HVCLPIFLKCTDAB-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C(F)(F)F)=C1 HVCLPIFLKCTDAB-UHFFFAOYSA-N 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• MXWDEFJGDAATQG-UHFFFAOYSA-N N-(cyclopropylmethyl)-3,5-dicyclopropyloxy-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]benzamide Chemical compound C1(CC1)OC=1C=C(C(=O)N(C(C)C=2N(N=CN=2)C2=NC=CC=N2)CC2CC2)C=C(C=1)OC1CC1 MXWDEFJGDAATQG-UHFFFAOYSA-N 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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• NGCHHOUXDHNUJM-UHFFFAOYSA-N 3-(2-cyanopropan-2-yloxy)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide Chemical compound C(#N)C(C)(OC=1C=C(C(=O)NC(C)C=2N(N=CN=2)C2=NC=CC=N2)C=C(C=1)C(F)(F)F)C NGCHHOUXDHNUJM-UHFFFAOYSA-N 0.000 description 7
• DRSRKKJTSUVRLG-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-N-(cyclopropylmethyl)-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-5-(trifluoromethyl)benzamide Chemical compound C1(CC1)COC=1C=C(C(=O)N(C(C)C=2N(N=CN=2)C2=NC=CC=N2)CC2CC2)C=C(C=1)C(F)(F)F DRSRKKJTSUVRLG-UHFFFAOYSA-N 0.000 description 7
• 239000005944 Chlorpyrifos Substances 0.000 description 7
• 235000010469 Glycine max Nutrition 0.000 description 7
• 244000068988 Glycine max Species 0.000 description 7
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• 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 7
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• IORPESXQQCAORG-UHFFFAOYSA-N N-(cyclopropylmethyl)-2-methylsulfonyl-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-6-(trifluoromethyl)pyridine-4-carboxamide Chemical compound C1(CC1)CN(C(=O)C1=CC(=NC(=C1)C(F)(F)F)S(=O)(=O)C)C(C)C=1N(N=CN=1)C1=NC=CC=N1 IORPESXQQCAORG-UHFFFAOYSA-N 0.000 description 7
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• 125000003545 alkoxy group Chemical group 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
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• SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
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• 239000000543 intermediate Substances 0.000 description 7
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• MVILWLLYYQVYNH-UHFFFAOYSA-N pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC=N1.NC(=O)C1=CC=CC=N1 MVILWLLYYQVYNH-UHFFFAOYSA-N 0.000 description 7
• 235000009566 rice Nutrition 0.000 description 7
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