JP5243960B2 - 殺菌活性を有するチエノ−ピリミジン化合物 - Google Patents

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Publication number

JP5243960B2

JP5243960B2 JP2008536556A JP2008536556A JP5243960B2 JP 5243960 B2 JP5243960 B2 JP 5243960B2 JP 2008536556 A JP2008536556 A JP 2008536556A JP 2008536556 A JP2008536556 A JP 2008536556A JP 5243960 B2 JP5243960 B2 JP 5243960B2

Authority

JP

Japan

Prior art keywords

mmol

compound

compounds

insecticides

added

Prior art date

2005-10-21

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.)

Expired - Fee Related

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• 230000000844 anti-bacterial effect Effects 0.000 title claims description 12
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title claims description 8
• 150000001875 compounds Chemical class 0.000 claims description 143
• -1 hydrazidecarbonyl Chemical group 0.000 claims description 77
• 239000000203 mixture Substances 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 27
• 241000233866 Fungi Species 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 239000002689 soil Substances 0.000 claims description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical group 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• 230000002538 fungal effect Effects 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
• 239000012876 carrier material Substances 0.000 claims description 2
• 230000009545 invasion Effects 0.000 claims description 2
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 2
• 150000003222 pyridines Chemical class 0.000 claims description 2
• 241000196324 Embryophyta Species 0.000 description 62
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• 239000002917 insecticide Substances 0.000 description 49
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• 239000000243 solution Substances 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
• 239000007787 solid Substances 0.000 description 32
• 239000002904 solvent Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 239000011734 sodium Substances 0.000 description 25
• 238000002360 preparation method Methods 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• 239000012267 brine Substances 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 238000009472 formulation Methods 0.000 description 20
• 239000000417 fungicide Substances 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 239000000843 powder Substances 0.000 description 18
• 238000001914 filtration Methods 0.000 description 17
• 238000012360 testing method Methods 0.000 description 16
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• 239000000575 pesticide Substances 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• 201000010099 disease Diseases 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000007788 liquid Substances 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• 241000209140 Triticum Species 0.000 description 11
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• 240000008067 Cucumis sativus Species 0.000 description 8
• 235000021307 Triticum Nutrition 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 150000003839 salts Chemical class 0.000 description 8
• 239000004094 surface-active agent Substances 0.000 description 8
• 206010061818 Disease progression Diseases 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 230000005750 disease progression Effects 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
• 241000221785 Erysiphales Species 0.000 description 6
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000007900 aqueous suspension Substances 0.000 description 6
• 239000004495 emulsifiable concentrate Substances 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 244000052769 pathogen Species 0.000 description 6
• 230000001717 pathogenic effect Effects 0.000 description 6
• 239000000377 silicon dioxide Substances 0.000 description 6
• 239000002002 slurry Substances 0.000 description 6
• DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 230000000749 insecticidal effect Effects 0.000 description 5
• 239000004533 oil dispersion Substances 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• QXJAJOAGCZNLMB-UHFFFAOYSA-N 4-[2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCNC1=NC=NC2=C1C(Cl)=CS2 QXJAJOAGCZNLMB-UHFFFAOYSA-N 0.000 description 4
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
• 240000007594 Oryza sativa Species 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 240000003768 Solanum lycopersicum Species 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 230000000855 fungicidal effect Effects 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 239000003415 peat Substances 0.000 description 4
• 230000003032 phytopathogenic effect Effects 0.000 description 4
• ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
• 235000009566 rice Nutrition 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• 239000002169 Metam Substances 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
• 125000000304 alkynyl group Chemical group 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 230000001580 bacterial effect Effects 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 239000012230 colorless oil Substances 0.000 description 3
• 239000012141 concentrate Substances 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 239000002949 juvenile hormone Chemical class 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 229960002523 mercuric chloride Drugs 0.000 description 3
• LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
• 235000010446 mineral oil Nutrition 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
• 239000005077 polysulfide Substances 0.000 description 3
• 229920001021 polysulfide Polymers 0.000 description 3
• 150000008117 polysulfides Polymers 0.000 description 3
• 239000002728 pyrethroid Substances 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 241000894007 species Species 0.000 description 3
• 239000007921 spray Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 229960003732 tyramine Drugs 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
• XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
• CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 2
• KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
• RLLPVAHGXHCWKJ-MJGOQNOKSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-MJGOQNOKSA-N 0.000 description 2
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
• CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
• RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
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• MBTGBRYMJKYYOE-UHFFFAOYSA-N 2,6-difluoropyridine Chemical compound FC1=CC=CC(F)=N1 MBTGBRYMJKYYOE-UHFFFAOYSA-N 0.000 description 2
• MPUUPHNZUMFOSI-UHFFFAOYSA-N 2-(benzylamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1NCC1=CC=CC=C1 MPUUPHNZUMFOSI-UHFFFAOYSA-N 0.000 description 2
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
• JZXVPAJGIVSUOO-UHFFFAOYSA-N 3-[2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl]phenol Chemical compound OC1=CC=CC(CCNC=2C=3C(Cl)=CSC=3N=CN=2)=C1 JZXVPAJGIVSUOO-UHFFFAOYSA-N 0.000 description 2
• FNQYPHFVROWTIU-UHFFFAOYSA-N 3-tert-butyl-5-(6-chloropyridin-2-yl)-1,2,4-oxadiazole Chemical compound CC(C)(C)C1=NOC(C=2N=C(Cl)C=CC=2)=N1 FNQYPHFVROWTIU-UHFFFAOYSA-N 0.000 description 2
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• XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 2
• JCXBWISGPRZELZ-UHFFFAOYSA-N 5-methyl-6-methylsulfanylpyridin-3-amine Chemical compound CSC1=NC=C(N)C=C1C JCXBWISGPRZELZ-UHFFFAOYSA-N 0.000 description 2
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
• 239000005660 Abamectin Substances 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 239000005944 Chlorpyrifos Substances 0.000 description 2
• 239000005945 Chlorpyrifos-methyl Substances 0.000 description 2
• IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 2
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