WO1993013664A2 - Composes fongicides biheterocycliques - Google Patents
Composes fongicides biheterocycliques Download PDFInfo
- Publication number
- WO1993013664A2 WO1993013664A2 PCT/GB1993/000029 GB9300029W WO9313664A2 WO 1993013664 A2 WO1993013664 A2 WO 1993013664A2 GB 9300029 W GB9300029 W GB 9300029W WO 9313664 A2 WO9313664 A2 WO 9313664A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- optionally substituted
- ring
- give
- carboxylate
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 218
- 230000000855 fungicidal effect Effects 0.000 title description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract description 9
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 7
- 241000233866 Fungi Species 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims abstract description 3
- -1 phenylcarbamoyl Chemical group 0.000 claims description 56
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 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
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000005415 substituted alkoxy 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 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- VQUBNHJPURYQRZ-UHFFFAOYSA-N thieno[2,3-b]pyridin-3-ol Chemical compound C1=CC=C2C(O)=CSC2=N1 VQUBNHJPURYQRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 26
- 238000010898 silica gel chromatography Methods 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000000284 extract Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000012312 sodium hydride Substances 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000012258 stirred mixture Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- VNGMVGWUWHNBBW-UHFFFAOYSA-N methyl 3-hydroxythieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(O)=C(C(=O)OC)SC2=N1 VNGMVGWUWHNBBW-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 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 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- WTAZYMOAYFJBPE-UHFFFAOYSA-N 2-(2-methoxypropyl)-1,1-dioxothieno[2,3-b]pyridin-3-one Chemical compound C1=CN=C2S(=O)(=O)C(CC(C)OC)C(=O)C2=C1 WTAZYMOAYFJBPE-UHFFFAOYSA-N 0.000 description 2
- BROCKUOWLSSWDC-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanylcarbothioyloxythieno[2,3-b]pyridine-2-carboxylic acid Chemical compound OC(=O)C=1SC2=NC=CC=C2C=1OC(=S)SC1=CC=C(Cl)C=C1 BROCKUOWLSSWDC-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- YVYQYTWFDUOYPC-UHFFFAOYSA-N 3-hydroxythieno[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(=O)O)SC2=N1 YVYQYTWFDUOYPC-UHFFFAOYSA-N 0.000 description 2
- BCFOJDYDKLWFKB-UHFFFAOYSA-N 3-methoxy-2-(2-phenylethynyl)thieno[2,3-b]pyridine Chemical compound S1C2=NC=CC=C2C(OC)=C1C#CC1=CC=CC=C1 BCFOJDYDKLWFKB-UHFFFAOYSA-N 0.000 description 2
- XKFKZVHFDUQNRH-UHFFFAOYSA-N 3-methoxy-2-methylthieno[2,3-b]pyridine 1,1-dioxide Chemical compound C1=CC=C2C(OC)=C(C)S(=O)(=O)C2=N1 XKFKZVHFDUQNRH-UHFFFAOYSA-N 0.000 description 2
- CZGBNQUOOFCFKJ-UHFFFAOYSA-N 3-methoxythieno[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2C(OC)=C(C(O)=O)SC2=N1 CZGBNQUOOFCFKJ-UHFFFAOYSA-N 0.000 description 2
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241001668536 Oculimacula yallundae Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001617088 Thanatephorus sasakii Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- NSIJTLULGVMZFY-UHFFFAOYSA-N cyclohexyl 3-hydroxy-5-oxidothieno[3,2-c]pyridin-5-ium-2-carboxylate Chemical compound S1C2=CC=[N+]([O-])C=C2C(O)=C1C(=O)OC1CCCCC1 NSIJTLULGVMZFY-UHFFFAOYSA-N 0.000 description 2
- WKQKSOPEDZWUEA-UHFFFAOYSA-N cyclohexyl 3-hydroxythieno[3,2-b]pyridine-2-carboxylate Chemical compound S1C2=CC=CN=C2C(O)=C1C(=O)OC1CCCCC1 WKQKSOPEDZWUEA-UHFFFAOYSA-N 0.000 description 2
- FXHUTXJYNMDGKN-UHFFFAOYSA-N cyclohexyl 5-acetyl-3-amino-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate Chemical compound NC=1C2=C(C)C(C(=O)C)=C(C)N=C2SC=1C(=O)OC1CCCCC1 FXHUTXJYNMDGKN-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- VKOUOLSMUSGVKZ-UHFFFAOYSA-N ethyl 4-methoxy-2-(2-oxo-2-propan-2-yloxyethyl)sulfanylquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(OC)C(C(=O)OCC)=C(SCC(=O)OC(C)C)N=C21 VKOUOLSMUSGVKZ-UHFFFAOYSA-N 0.000 description 2
- MAKZWGXOEKCMNV-UHFFFAOYSA-N ethyl 4-oxo-2-(2-oxo-2-propan-2-yloxyethyl)sulfanyl-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=C(SCC(=O)OC(C)C)NC2=C1 MAKZWGXOEKCMNV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BQQXUGGTSVMBLL-UHFFFAOYSA-N methyl 2-sulfanylidene-1h-pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CNC1=S BQQXUGGTSVMBLL-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KLHDJBCAYIXOTA-UHFFFAOYSA-N propan-2-yl 2-sulfanylacetate Chemical compound CC(C)OC(=O)CS KLHDJBCAYIXOTA-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- PWSBNTOBQBTNEJ-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=C[CH]C2=C=CSC2=N1 PWSBNTOBQBTNEJ-UHFFFAOYSA-N 0.000 description 2
- IODFIIZCMGDULB-UHFFFAOYSA-N thieno[3,2-b]pyridin-3-ol Chemical class C1=CN=C2C(O)=CSC2=C1 IODFIIZCMGDULB-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SLPHZQXLXZRRCE-UHFFFAOYSA-N (3-methoxythieno[2,3-b]pyridin-2-yl)methyl benzoate Chemical compound S1C2=NC=CC=C2C(OC)=C1COC(=O)C1=CC=CC=C1 SLPHZQXLXZRRCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WLTUFYJLCCSPKS-UHFFFAOYSA-N 1-(3-hydroxythieno[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one Chemical compound C1=CC=C2C(O)=C(C(=O)C(C)(C)C)SC2=N1 WLTUFYJLCCSPKS-UHFFFAOYSA-N 0.000 description 1
- ZNJDNGHDAKMZJN-UHFFFAOYSA-N 1-(3-hydroxythieno[2,3-b]pyridin-2-yl)ethanone Chemical compound C1=CC=C2C(O)=C(C(=O)C)SC2=N1 ZNJDNGHDAKMZJN-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- CJISJWDIVPROJF-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-3-methoxythieno[2,3-b]pyridine Chemical compound S1C2=NC=CC=C2C(OC)=C1C1OCCO1 CJISJWDIVPROJF-UHFFFAOYSA-N 0.000 description 1
- QJPGUOGGXXEKNG-UHFFFAOYSA-N 2-(2-methoxypropyl)thieno[2,3-b]pyridin-3-one Chemical compound C1=CC=C2C(=O)C(CC(C)OC)SC2=N1 QJPGUOGGXXEKNG-UHFFFAOYSA-N 0.000 description 1
- UBPFVQMKXPKJGC-UHFFFAOYSA-N 2-(3,3-dimethyl-2-oxobutyl)sulfanylpyridine-3-carboxylic acid Chemical compound CC(C)(C)C(=O)CSC1=NC=CC=C1C(O)=O UBPFVQMKXPKJGC-UHFFFAOYSA-N 0.000 description 1
- YILCSEPFRCCVIT-UHFFFAOYSA-N 2-(C-cyclohexyl-N-methoxycarbonimidoyl)thieno[2,3-b]pyridin-3-ol Chemical compound CON=C(C1CCCCC1)C1=C(C=2C(=NC=CC2)S1)O YILCSEPFRCCVIT-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 1
- JWIZEODTYIBLTL-UHFFFAOYSA-N 2-cyano-3-thiophen-2-ylprop-2-enethioamide Chemical compound NC(=S)C(C#N)=CC1=CC=CS1 JWIZEODTYIBLTL-UHFFFAOYSA-N 0.000 description 1
- BHPYMZQTCPRLNR-UHFFFAOYSA-N 2-cyanoethanethioamide Chemical compound NC(=S)CC#N BHPYMZQTCPRLNR-UHFFFAOYSA-N 0.000 description 1
- YNPTWGNKQDYUIO-UHFFFAOYSA-N 2-cyclohexyl-1,1-dioxothieno[2,3-b]pyridin-3-one Chemical compound O=S1(=O)C2=NC=CC=C2C(=O)C1C1CCCCC1 YNPTWGNKQDYUIO-UHFFFAOYSA-N 0.000 description 1
- FISGRLRRAVZZJZ-UHFFFAOYSA-N 2-methyl-1,1-dioxothieno[2,3-b]pyridin-3-one Chemical compound C1=CN=C2S(=O)(=O)C(C)C(=O)C2=C1 FISGRLRRAVZZJZ-UHFFFAOYSA-N 0.000 description 1
- JTROGFJDYGHBCQ-UHFFFAOYSA-N 2-methyl-1-oxothieno[2,3-b]pyridin-3-ol Chemical compound C1=CN=C2S(=O)C(C)=C(O)C2=C1 JTROGFJDYGHBCQ-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- NAGNTUBTOMNNRR-UHFFFAOYSA-N 2-o-cyclohexyl 4-o-ethyl 3-amino-6-methylthieno[2,3-b]pyridine-2,4-dicarboxylate Chemical compound NC=1C=2C(C(=O)OCC)=CC(C)=NC=2SC=1C(=O)OC1CCCCC1 NAGNTUBTOMNNRR-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WYKHFQKONWMWQM-UHFFFAOYSA-N 2-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1S WYKHFQKONWMWQM-UHFFFAOYSA-N 0.000 description 1
- FRFLZONFDXWIHG-UHFFFAOYSA-N 2-thieno[2,3-b]pyridin-3-yloxyacetonitrile Chemical compound C1=CC=C2C(OCC#N)=CSC2=N1 FRFLZONFDXWIHG-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- TZZDVPMABRWKIZ-MFTLXVFQSA-N 3-[6-[4-[[1-[4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OC=1C=C2CC[C@@H]([C@@H](C2=CC=1)C1=CC=C(C=C1)N1CCC(CC1)CN1CCN(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C1=CC=CC=C1 TZZDVPMABRWKIZ-MFTLXVFQSA-N 0.000 description 1
- FDWWWHRHTGIPNF-UHFFFAOYSA-N 3-hydroxy-n-phenylthieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 FDWWWHRHTGIPNF-UHFFFAOYSA-N 0.000 description 1
- GBCOPHSMRFZJIL-UHFFFAOYSA-N 3-hydroxythieno[2,3-b]pyridine-2-carbonitrile Chemical compound C1=CC=C2C(O)=C(C#N)SC2=N1 GBCOPHSMRFZJIL-UHFFFAOYSA-N 0.000 description 1
- PREDRCIEXBCVJM-UHFFFAOYSA-N 3-methoxy-2-(2-methoxypropyl)thieno[2,3-b]pyridine 1,1-dioxide Chemical compound C1=CN=C2S(=O)(=O)C(CC(C)OC)=C(OC)C2=C1 PREDRCIEXBCVJM-UHFFFAOYSA-N 0.000 description 1
- NEFHWXJPLJPGOF-UHFFFAOYSA-N 3-methoxy-2-methylthieno[2,3-b]pyridine Chemical compound C1=CC=C2C(OC)=C(C)SC2=N1 NEFHWXJPLJPGOF-UHFFFAOYSA-N 0.000 description 1
- XBSJAUISGGVNJJ-UHFFFAOYSA-N 3-methoxy-4-methylthieno[2,3-b]pyridin-2-ol Chemical compound C1=CC(C)=C2C(OC)=C(O)SC2=N1 XBSJAUISGGVNJJ-UHFFFAOYSA-N 0.000 description 1
- DCRPSNKQBNLJCW-UHFFFAOYSA-N 3-methoxy-n',n'-dimethylthieno[2,3-b]pyridine-2-carbohydrazide Chemical compound C1=CC=C2C(OC)=C(C(=O)NN(C)C)SC2=N1 DCRPSNKQBNLJCW-UHFFFAOYSA-N 0.000 description 1
- JEKGBXLWQGYJHT-UHFFFAOYSA-N 3-methoxythieno[2,3-b]pyridine Chemical compound C1=CC=C2C(OC)=CSC2=N1 JEKGBXLWQGYJHT-UHFFFAOYSA-N 0.000 description 1
- GSZWWFGCPOQERP-UHFFFAOYSA-N 3-methoxythieno[2,3-b]pyridine-2-carbaldehyde Chemical compound C1=CC=C2C(OC)=C(C=O)SC2=N1 GSZWWFGCPOQERP-UHFFFAOYSA-N 0.000 description 1
- GCZXJYGQOYBXDR-UHFFFAOYSA-N 3-methoxythieno[2,3-b]pyridine-2-carbonyl chloride Chemical compound C1=CC=C2C(OC)=C(C(Cl)=O)SC2=N1 GCZXJYGQOYBXDR-UHFFFAOYSA-N 0.000 description 1
- GSGLJVKRQQJKEG-UHFFFAOYSA-N 3-prop-2-ynoxythieno[2,3-b]quinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(C(=C(C(=O)O)S3)OCC#C)C3=NC2=C1 GSGLJVKRQQJKEG-UHFFFAOYSA-N 0.000 description 1
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- SHBJTJAPGQUEPP-UHFFFAOYSA-N 4-ethyl-6-methyl-2-sulfanylidene-1H-pyridine-3-carbonitrile Chemical compound C(C)C1=C(C(=NC(=C1)C)S)C#N SHBJTJAPGQUEPP-UHFFFAOYSA-N 0.000 description 1
- VNQQSJXKDMDYAZ-UHFFFAOYSA-N 4-methoxy-5-methyl-6-methylsulfanyl-2-phenylpyrimidine Chemical compound CSC1=C(C)C(OC)=NC(C=2C=CC=CC=2)=N1 VNQQSJXKDMDYAZ-UHFFFAOYSA-N 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- IOVNUCBOCOSPGO-UHFFFAOYSA-N 5-acetyl-6-methyl-2-sulfanylidene-4-thiophen-2-yl-1h-pyridine-3-carbonitrile Chemical compound CC(=O)C1=C(C)NC(=S)C(C#N)=C1C1=CC=CS1 IOVNUCBOCOSPGO-UHFFFAOYSA-N 0.000 description 1
- HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
- VOEHPGNQQRPOOU-UHFFFAOYSA-N 6-isocyanatohexanenitrile Chemical compound O=C=NCCCCCC#N VOEHPGNQQRPOOU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- YBKIZMSUWVWWMI-UHFFFAOYSA-N C1=CC=C2C(OC)=C(C(OCC#N)=C(S3)C(O)=O)C3=NC2=C1 Chemical compound C1=CC=C2C(OC)=C(C(OCC#N)=C(S3)C(O)=O)C3=NC2=C1 YBKIZMSUWVWWMI-UHFFFAOYSA-N 0.000 description 1
- PMKHOYOFADUQPD-UHFFFAOYSA-N CC(C)OC(=O)C=1SC=2N=C3C=CC=CN3C(=O)C=2C=1OC(=O)C1=CC=CC(C)=C1 Chemical compound CC(C)OC(=O)C=1SC=2N=C3C=CC=CN3C(=O)C=2C=1OC(=O)C1=CC=CC(C)=C1 PMKHOYOFADUQPD-UHFFFAOYSA-N 0.000 description 1
- SYZOFRXZMALRGI-JYJNAYRXSA-N CC1=C(NCC(F)(F)F)C(=O)N(C=C1)[C@@H](CC1CC1)C(=O)N[C@@H](C[C@@H]1CCNC1=O)C#N Chemical compound CC1=C(NCC(F)(F)F)C(=O)N(C=C1)[C@@H](CC1CC1)C(=O)N[C@@H](C[C@@H]1CCNC1=O)C#N SYZOFRXZMALRGI-JYJNAYRXSA-N 0.000 description 1
- VGKAAMLPCAJHEH-UHFFFAOYSA-N CSC(=C1COC(OC1)(C)C)SC Chemical compound CSC(=C1COC(OC1)(C)C)SC VGKAAMLPCAJHEH-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 241000400611 Eucalyptus deanei Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- FRYUUTZQHXAQSQ-UHFFFAOYSA-N N1=C2C=CC=CN2C(=O)C2=C1SC(C(=O)OC(C)C)=C2OC(=O)NCCCC Chemical compound N1=C2C=CC=CN2C(=O)C2=C1SC(C(=O)OC(C)C)=C2OC(=O)NCCCC FRYUUTZQHXAQSQ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- HNTNNLWOQREFLL-UHFFFAOYSA-N O-cyclohexyl 3-hydroxy-4-methylthieno[3,2-c]quinoline-2-carbothioate Chemical compound OC1=C(SC2=C1C(=NC=1C=CC=CC2=1)C)C(=S)OC1CCCCC1 HNTNNLWOQREFLL-UHFFFAOYSA-N 0.000 description 1
- QMACXQZYGQAOKG-UHFFFAOYSA-N O-cyclohexyl 5-hydroxy-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound OC1=C(SC=2N=C(N=CC=21)C)C(=S)OC1CCCCC1 QMACXQZYGQAOKG-UHFFFAOYSA-N 0.000 description 1
- NIBPBGGNJZNNNN-UHFFFAOYSA-N O-methyl 5-hydroxy-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound OC1=C(SC=2N=C(N=CC=21)C)C(=S)OC NIBPBGGNJZNNNN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- JCXPAHAYLMENKT-UHFFFAOYSA-N S1C=2N=C3C=CC=CN3C(=O)C=2C(O)=C1C(=O)OC1CCCCC1 Chemical compound S1C=2N=C3C=CC=CN3C(=O)C=2C(O)=C1C(=O)OC1CCCCC1 JCXPAHAYLMENKT-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfate Natural products OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- DYPUEYQCOVBHQR-UHFFFAOYSA-N [2-(2,2-dimethylpropanoyl)thieno[2,3-b]pyridin-3-yl] acetate Chemical compound C1=CC=C2C(OC(=O)C)=C(C(=O)C(C)(C)C)SC2=N1 DYPUEYQCOVBHQR-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000005604 azodicarboxylate group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- GUUHSHAWOOMFMF-UHFFFAOYSA-N bis[(4-chlorophenyl)sulfanyl]methanethione Chemical compound C1=CC(Cl)=CC=C1SC(=S)SC1=CC=C(Cl)C=C1 GUUHSHAWOOMFMF-UHFFFAOYSA-N 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- CZKGHNHQNPLNKR-UHFFFAOYSA-N cyclohexyl 2-(6-amino-3,5-dicyano-4-methylsulfanylpyridin-2-yl)sulfanylacetate Chemical compound CSC1=C(C#N)C(N)=NC(SCC(=O)OC2CCCCC2)=C1C#N CZKGHNHQNPLNKR-UHFFFAOYSA-N 0.000 description 1
- JTYINBWQGXHZLX-UHFFFAOYSA-N cyclohexyl 2-bromoacetate Chemical compound BrCC(=O)OC1CCCCC1 JTYINBWQGXHZLX-UHFFFAOYSA-N 0.000 description 1
- IBFHBLOKQVCABG-UHFFFAOYSA-N cyclohexyl 2-chloroacetate Chemical compound ClCC(=O)OC1CCCCC1 IBFHBLOKQVCABG-UHFFFAOYSA-N 0.000 description 1
- SYNLVXCQXYVPOA-UHFFFAOYSA-N cyclohexyl 2-hydroxyacetate Chemical compound OCC(=O)OC1CCCCC1 SYNLVXCQXYVPOA-UHFFFAOYSA-N 0.000 description 1
- GINCKTWFJHUYLR-UHFFFAOYSA-N cyclohexyl 3-(5-cyanopentylcarbamoyloxy)thieno[2,3-b]quinoline-2-carboxylate Chemical compound S1C2=NC3=CC=CC=C3C=C2C(OC(NCCCCCC#N)=O)=C1C(=O)OC1CCCCC1 GINCKTWFJHUYLR-UHFFFAOYSA-N 0.000 description 1
- UPMSWNPFZJSOJP-UHFFFAOYSA-N cyclohexyl 3-(methanesulfonamido)thieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=CC=C2C(NS(=O)(=O)C)=C1C(=O)OC1CCCCC1 UPMSWNPFZJSOJP-UHFFFAOYSA-N 0.000 description 1
- UCIVJMZPSZHKMF-UHFFFAOYSA-N cyclohexyl 3-(methoxycarbonylamino)thieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=CC=C2C(NC(=O)OC)=C1C(=O)OC1CCCCC1 UCIVJMZPSZHKMF-UHFFFAOYSA-N 0.000 description 1
- TUJFUAPQDJZVLN-UHFFFAOYSA-N cyclohexyl 3-(trifluoromethylsulfonylamino)thieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=CC=C2C(NS(=O)(=O)C(F)(F)F)=C1C(=O)OC1CCCCC1 TUJFUAPQDJZVLN-UHFFFAOYSA-N 0.000 description 1
- HTFKGQHOCRJTLI-UHFFFAOYSA-N cyclohexyl 3-[bis(trifluoromethylsulfonyl)amino]thieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=CC=C2C(N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)=C1C(=O)OC1CCCCC1 HTFKGQHOCRJTLI-UHFFFAOYSA-N 0.000 description 1
- GKUHWIZQWWSPTD-UHFFFAOYSA-N cyclohexyl 3-acetyloxy-6-methylthieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC(C)=CC=C2C(OC(=O)C)=C1C(=O)OC1CCCCC1 GKUHWIZQWWSPTD-UHFFFAOYSA-N 0.000 description 1
- POAJSGKBUKXBEG-UHFFFAOYSA-N cyclohexyl 3-amino-5-chloro-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate Chemical compound NC=1C=2C(C)=C(Cl)C(C)=NC=2SC=1C(=O)OC1CCCCC1 POAJSGKBUKXBEG-UHFFFAOYSA-N 0.000 description 1
- UGQIJZKGOFFRAS-UHFFFAOYSA-N cyclohexyl 3-hydroxy-5-nitrothieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=C([N+]([O-])=O)C=C2C(O)=C1C(=O)OC1CCCCC1 UGQIJZKGOFFRAS-UHFFFAOYSA-N 0.000 description 1
- AJUKEDUSFKRAFI-UHFFFAOYSA-N cyclohexyl 3-hydroxy-6-methoxythieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC(OC)=CC=C2C(O)=C1C(=O)OC1CCCCC1 AJUKEDUSFKRAFI-UHFFFAOYSA-N 0.000 description 1
- ZJGSJOJKOTZUCJ-UHFFFAOYSA-N cyclohexyl 3-hydroxy-6-methylthieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC(C)=CC=C2C(O)=C1C(=O)OC1CCCCC1 ZJGSJOJKOTZUCJ-UHFFFAOYSA-N 0.000 description 1
- NIPPRISHWNFKIK-UHFFFAOYSA-N cyclohexyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate Chemical compound O1C2=NC=CC=C2C(O)=C1C(=O)OC1CCCCC1 NIPPRISHWNFKIK-UHFFFAOYSA-N 0.000 description 1
- FUSLFKJJJNVUCS-UHFFFAOYSA-N cyclohexyl 3-hydroxythieno[2,3-b]pyridine-2-carboxylate Chemical compound S1C2=NC=CC=C2C(O)=C1C(=O)OC1CCCCC1 FUSLFKJJJNVUCS-UHFFFAOYSA-N 0.000 description 1
- VDXAOEDKMCVJFP-UHFFFAOYSA-N cyclohexyl 3-hydroxythieno[2,3-b]quinoline-2-carboxylate Chemical compound S1C2=NC3=CC=CC=C3C=C2C(O)=C1C(=O)OC1CCCCC1 VDXAOEDKMCVJFP-UHFFFAOYSA-N 0.000 description 1
- RZJWOOIIJOHEFN-UHFFFAOYSA-N cyclohexyl 3-methoxycarbonyloxyfuro[2,3-b]pyridine-2-carboxylate Chemical compound O1C2=NC=CC=C2C(OC(=O)OC)=C1C(=O)OC1CCCCC1 RZJWOOIIJOHEFN-UHFFFAOYSA-N 0.000 description 1
- ZTLKVSCOVOGNAM-UHFFFAOYSA-N cyclohexyl 5-hydroxy-2-methylsulfonylthieno[2,3-d]pyrimidine-6-carboxylate Chemical compound S1C2=NC(S(=O)(=O)C)=NC=C2C(O)=C1C(=O)OC1CCCCC1 ZTLKVSCOVOGNAM-UHFFFAOYSA-N 0.000 description 1
- HFPAXDSZODZVFJ-UHFFFAOYSA-N cyclohexyl 5-hydroxy-2-phenoxythieno[2,3-d]pyrimidine-6-carboxylate Chemical compound N=1C=C2C(O)=C(C(=O)OC3CCCCC3)SC2=NC=1OC1=CC=CC=C1 HFPAXDSZODZVFJ-UHFFFAOYSA-N 0.000 description 1
- FNFRRJBPELNXEJ-UHFFFAOYSA-N cyclohexyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate Chemical compound S1C2=NC=CN=C2C(N)=C1C(=O)OC1CCCCC1 FNFRRJBPELNXEJ-UHFFFAOYSA-N 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HEBBAHSTRIIXNR-UHFFFAOYSA-N diethyl 2-[anilino-(2-oxo-2-propan-2-yloxyethyl)sulfanylmethylidene]propanedioate Chemical compound CC(C)OC(=O)CSC(=C(C(=O)OCC)C(=O)OCC)NC1=CC=CC=C1 HEBBAHSTRIIXNR-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- FPUWAOISRLVMAP-UHFFFAOYSA-N ethyl 2-(3-methoxythieno[2,3-b]pyridin-2-yl)-2-oxoacetate Chemical compound C1=CC=C2C(OC)=C(C(=O)C(=O)OCC)SC2=N1 FPUWAOISRLVMAP-UHFFFAOYSA-N 0.000 description 1
- YVYCNIQHHMEEHM-UHFFFAOYSA-N ethyl 2-methylsulfanyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1=CC=CN2C(=O)C(C(=O)OCC)=C(SC)N=C21 YVYCNIQHHMEEHM-UHFFFAOYSA-N 0.000 description 1
- GDHPVMDAKMWERF-UHFFFAOYSA-N ethyl 2-methylsulfanyl-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC=CC=C2N2C1=NC(SC)=C(C(=O)OCC)C2=O GDHPVMDAKMWERF-UHFFFAOYSA-N 0.000 description 1
- LTMSGJPYYUEEPR-UHFFFAOYSA-N ethyl 3-cyano-2-(2-cyclohexyloxy-2-oxoethyl)sulfanyl-6-methylpyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC(C)=NC(SCC(=O)OC2CCCCC2)=C1C#N LTMSGJPYYUEEPR-UHFFFAOYSA-N 0.000 description 1
- BFSADMQPFIWOPB-UHFFFAOYSA-N ethyl 3-methoxythieno[2,3-b]pyridine-2-sulfonate Chemical compound C1=CC=C2C(OC)=C(S(=O)(=O)OCC)SC2=N1 BFSADMQPFIWOPB-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 244000000008 fungal human pathogen Species 0.000 description 1
- IZLZCXOWFDCZLD-UHFFFAOYSA-N furo[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2OC(C(=O)O)=CC2=C1 IZLZCXOWFDCZLD-UHFFFAOYSA-N 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- CDEHWNZJIVRVOS-UHFFFAOYSA-N methyl 2-(cyanomethylsulfanyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1SCC#N CDEHWNZJIVRVOS-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- MYGAJZBZLONIBZ-UHFFFAOYSA-N methyl 2-chloropyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1Cl MYGAJZBZLONIBZ-UHFFFAOYSA-N 0.000 description 1
- FASOJOLGUAUEPU-UHFFFAOYSA-N methyl 3-bromopyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1Br FASOJOLGUAUEPU-UHFFFAOYSA-N 0.000 description 1
- COMSYKQXHQKFHA-UHFFFAOYSA-N methyl 4-methoxy-6-methylsulfonyl-2-phenylpyrimidine-5-carboxylate Chemical compound N1=C(S(C)(=O)=O)C(C(=O)OC)=C(OC)N=C1C1=CC=CC=C1 COMSYKQXHQKFHA-UHFFFAOYSA-N 0.000 description 1
- DUFVWIHMRDQMJJ-UHFFFAOYSA-N methyl 4-methylsulfanyl-6-oxo-2-phenyl-1h-pyrimidine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=C(SC)N=C1C1=CC=CC=C1 DUFVWIHMRDQMJJ-UHFFFAOYSA-N 0.000 description 1
- ZKYUWXQPZPZJFR-UHFFFAOYSA-N methyl 5-acetyl-3-amino-6-methyl-4-thiophen-2-ylthieno[2,3-b]pyridine-2-carboxylate Chemical compound C=12C(N)=C(C(=O)OC)SC2=NC(C)=C(C(C)=O)C=1C1=CC=CS1 ZKYUWXQPZPZJFR-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- TXPUWXMGKDGSSE-UHFFFAOYSA-N n-cyclohexyl-3-methoxythieno[2,3-b]pyridine-2-carboxamide Chemical compound S1C2=NC=CC=C2C(OC)=C1C(=O)NC1CCCCC1 TXPUWXMGKDGSSE-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- CFLDXCRYDHZNLT-UHFFFAOYSA-N o-cyclohexyl 3,6-diamino-5-cyano-4-methylthieno[2,3-b]pyridine-2-carbothioate Chemical compound NC=1C=2C(C)=C(C#N)C(N)=NC=2SC=1C(=S)OC1CCCCC1 CFLDXCRYDHZNLT-UHFFFAOYSA-N 0.000 description 1
- ULILXQCXFAQLSZ-UHFFFAOYSA-N o-cyclohexyl 3-(5-cyanopentylcarbamoyloxy)-4-methylthieno[3,2-c]quinoline-2-carbothioate Chemical compound N#CCCCCCNC(=O)OC=1C=2C(C)=NC3=CC=CC=C3C=2SC=1C(=S)OC1CCCCC1 ULILXQCXFAQLSZ-UHFFFAOYSA-N 0.000 description 1
- OXUCOTSGWGNWGC-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2-] OXUCOTSGWGNWGC-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 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 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KNKVAUDQVGHCSM-UHFFFAOYSA-N propan-2-yl 2-chloropyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1Cl KNKVAUDQVGHCSM-UHFFFAOYSA-N 0.000 description 1
- YQHLKBJNIVKASU-UHFFFAOYSA-N propan-2-yl 3-(2-trimethylsilylethoxymethoxy)thieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OCOCC[Si](C)(C)C)=C(C(=O)OC(C)C)SC2=N1 YQHLKBJNIVKASU-UHFFFAOYSA-N 0.000 description 1
- QYQCDPIQNVSYIV-UHFFFAOYSA-N propan-2-yl 3-(3-iodoprop-2-ynoxy)thieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OCC#CI)=C(C(=O)OC(C)C)SC2=N1 QYQCDPIQNVSYIV-UHFFFAOYSA-N 0.000 description 1
- GWUHDVKTQNBALR-UHFFFAOYSA-N propan-2-yl 3-(4-aminobenzoyl)oxythieno[2,3-b]pyridine-2-carboxylate Chemical compound CC(C)OC(=O)C=1SC2=NC=CC=C2C=1OC(=O)C1=CC=C(N)C=C1 GWUHDVKTQNBALR-UHFFFAOYSA-N 0.000 description 1
- VZMSYMDBMKJGLX-UHFFFAOYSA-N propan-2-yl 3-(cyanomethoxy)thieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OCC#N)=C(C(=O)OC(C)C)SC2=N1 VZMSYMDBMKJGLX-UHFFFAOYSA-N 0.000 description 1
- DNPJZPKMADNXBB-UHFFFAOYSA-N propan-2-yl 3-(diacetylamino)thieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(N(C(C)=O)C(C)=O)=C(C(=O)OC(C)C)SC2=N1 DNPJZPKMADNXBB-UHFFFAOYSA-N 0.000 description 1
- ZLJKEBREJNCISR-UHFFFAOYSA-N propan-2-yl 3-aminothieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(N)=C(C(=O)OC(C)C)SC2=N1 ZLJKEBREJNCISR-UHFFFAOYSA-N 0.000 description 1
- OCFXOSJAVOCKOV-UHFFFAOYSA-N propan-2-yl 3-benzylsulfanylthieno[2,3-b]pyridine-2-carboxylate Chemical compound CC(C)OC(=O)C=1SC2=NC=CC=C2C=1SCC1=CC=CC=C1 OCFXOSJAVOCKOV-UHFFFAOYSA-N 0.000 description 1
- QEBNUBQHYQVRRO-UHFFFAOYSA-N propan-2-yl 3-diethoxyphosphoryloxythieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OP(=O)(OCC)OCC)=C(C(=O)OC(C)C)SC2=N1 QEBNUBQHYQVRRO-UHFFFAOYSA-N 0.000 description 1
- AWORQUYQNSYZAN-UHFFFAOYSA-N propan-2-yl 3-hydroxy-4-methoxythieno[2,3-b]quinoline-2-carboxylate Chemical compound C1=CC=C2C(OC)=C(C(O)=C(S3)C(=O)OC(C)C)C3=NC2=C1 AWORQUYQNSYZAN-UHFFFAOYSA-N 0.000 description 1
- ZVAHJISUQKEMII-UHFFFAOYSA-N propan-2-yl 3-hydroxy-4-oxo-9h-thieno[2,3-b]quinoline-2-carboxylate Chemical compound N1C2=CC=CC=C2C(=O)C2=C1SC(C(=O)OC(C)C)=C2O ZVAHJISUQKEMII-UHFFFAOYSA-N 0.000 description 1
- UHVXVGMFLZKLTR-UHFFFAOYSA-N propan-2-yl 3-hydroxy-4-propan-2-yloxythieno[2,3-b]quinoline-2-carboxylate Chemical compound C1=CC=C2C(OC(C)C)=C(C(=C(C(=O)OC(C)C)S3)O)C3=NC2=C1 UHVXVGMFLZKLTR-UHFFFAOYSA-N 0.000 description 1
- UJYYQKZFAOPGCI-UHFFFAOYSA-N propan-2-yl 3-hydroxythieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(O)=C(C(=O)OC(C)C)SC2=N1 UJYYQKZFAOPGCI-UHFFFAOYSA-N 0.000 description 1
- OFWMQOUEKFZWHS-UHFFFAOYSA-N propan-2-yl 3-hydroxythieno[2,3-b]quinoline-2-carboxylate Chemical compound C1=CC=C2C=C(C(=C(C(=O)OC(C)C)S3)O)C3=NC2=C1 OFWMQOUEKFZWHS-UHFFFAOYSA-N 0.000 description 1
- GDYXXAGYFFUVLK-UHFFFAOYSA-N propan-2-yl 3-hydroxythieno[2,3-c]pyridine-2-carboxylate Chemical compound N1=CC=C2C(O)=C(C(=O)OC(C)C)SC2=C1 GDYXXAGYFFUVLK-UHFFFAOYSA-N 0.000 description 1
- DMXDZJLSRHRQEI-UHFFFAOYSA-N propan-2-yl 3-methoxythieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OC)=C(C(=O)OC(C)C)SC2=N1 DMXDZJLSRHRQEI-UHFFFAOYSA-N 0.000 description 1
- JCHFQLXZRLMOLT-UHFFFAOYSA-N propan-2-yl 3-methylsulfonyloxythieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(OS(C)(=O)=O)=C(C(=O)OC(C)C)SC2=N1 JCHFQLXZRLMOLT-UHFFFAOYSA-N 0.000 description 1
- YHYDHHLWFYDENK-UHFFFAOYSA-N propan-2-yl 3-prop-2-ynylsulfanylthieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(SCC#C)=C(C(=O)OC(C)C)SC2=N1 YHYDHHLWFYDENK-UHFFFAOYSA-N 0.000 description 1
- FKSUHVURWAIHIF-UHFFFAOYSA-N propan-2-yl 4-(cyanomethoxy)-2-oxo-6-thia-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),4,8,10,12-pentaene-5-carboxylate Chemical compound N1=C2C=CC=CN2C(=O)C2=C1SC(C(=O)OC(C)C)=C2OCC#N FKSUHVURWAIHIF-UHFFFAOYSA-N 0.000 description 1
- NEXPFIPJVKVWBS-UHFFFAOYSA-N propan-2-yl 4-hydroxy-2-oxo-6-thia-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),4,8,10,12-pentaene-5-carboxylate Chemical compound N1=C2C=CC=CN2C(=O)C2=C1SC(C(=O)OC(C)C)=C2O NEXPFIPJVKVWBS-UHFFFAOYSA-N 0.000 description 1
- COIZHEDEBUDNIK-UHFFFAOYSA-N propan-2-yl 4-methoxy-3-prop-2-ynoxythieno[2,3-b]quinoline-2-carboxylate Chemical compound C1=CC=C2C(OC)=C(C(OCC#C)=C(S3)C(=O)OC(C)C)C3=NC2=C1 COIZHEDEBUDNIK-UHFFFAOYSA-N 0.000 description 1
- SLPCXKYWGLDULK-UHFFFAOYSA-N propan-2-yl 5-(cyanomethoxy)-4-methoxy-2-phenylthieno[2,3-d]pyrimidine-6-carboxylate Chemical compound N=1C=2SC(C(=O)OC(C)C)=C(OCC#N)C=2C(OC)=NC=1C1=CC=CC=C1 SLPCXKYWGLDULK-UHFFFAOYSA-N 0.000 description 1
- WEMINFWJAFANIQ-UHFFFAOYSA-N propan-2-yl 5-hydroxy-4-methoxy-2-phenylthieno[2,3-d]pyrimidine-6-carboxylate Chemical compound N=1C=2SC(C(=O)OC(C)C)=C(O)C=2C(OC)=NC=1C1=CC=CC=C1 WEMINFWJAFANIQ-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- BAQLNPIEFOYKNB-UHFFFAOYSA-N pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CC=N1 BAQLNPIEFOYKNB-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- XGCSHAYMNOFFNA-UHFFFAOYSA-N thieno[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2SC(C(=O)O)=CC2=C1 XGCSHAYMNOFFNA-UHFFFAOYSA-N 0.000 description 1
- AIWIVJNRSOBFST-UHFFFAOYSA-N thieno[2,3-b]quinoline Chemical group C1=CC=C2N=C(SC=C3)C3=CC2=C1 AIWIVJNRSOBFST-UHFFFAOYSA-N 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Definitions
- heterocyclyl Especially preferred substituents are hydroxy, chloro, cyano, amino, diethylamino, methyl, methoxy, phenoxy, methylthio, isopropylthio,
- the compounds of the invention are generally formulated in conventional compositions used for fungicides. These compositions can contain one or more additional agents.
- naphthalene-formaldehyde condensates salts of sulfonated phenol-formaldehyde condensates; or more complex
- Leptosphaeria nodorum glume blotch (LN)
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
L'invention se rapporte aux composés de la formule (I) dans laquelle le noyau A est un noyau éventuellement substitué à six membres contenant un ou deux atomes d'azote; x représente 0,5 ou -NR3-; R1 représente Q, cyano, halogène ou nitro; Q représente hydrogène, acyle, -C(=W)R5, -SR3, -C(=NR3)NR4R5, -C(=NR?3)OR4, -C(OR5)R3R4¿, alkyle éventuellement substitué, cycloalkyle éventuellement substitué, alcényle éventuellement substitué, alkynyle éventuellement substitué, aryle ou hétérocyclyle; R2 représente Q, ou -SIR3R4R5, ou lorsque X représente O ou NR3, peut également être -OR4; W représente NR?3, NOR3 ou NNR4R5¿; Z représente S(O)¿n? ou O; R?3, R4 et R5¿, qui peuvent être identiques ou différents, représentent hydrogène, alkyle éventuellement substitué, cycloalkyle éventuellement substitué, alcényle éventuellement substitué, alkynyle éventuellement substitué, aryle ou hétérocyclyle ou R?3 et R4 ou R4 et R5¿ ensemble avec l'atome auquel ils sont rattachés peuvent former un noyau; et n est 0, 1 ou 2. Ces composés peuvent être utilisés pour combattre des champignons phytopathogènes. Beaucoup de ces composés sont nouveaux.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9200557.8 | 1992-01-11 | ||
GB929200557A GB9200557D0 (en) | 1992-01-11 | 1992-01-11 | Pesticides |
GB9213145.7 | 1992-06-20 | ||
GB929213145A GB9213145D0 (en) | 1992-06-20 | 1992-06-20 | Fungicides |
GB9213148.1 | 1992-06-20 | ||
GB929213148A GB9213148D0 (en) | 1992-06-20 | 1992-06-20 | Fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993013664A2 true WO1993013664A2 (fr) | 1993-07-22 |
Family
ID=27265999
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1993/000029 WO1993013664A2 (fr) | 1992-01-11 | 1993-01-08 | Composes fongicides biheterocycliques |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU3262593A (fr) |
WO (1) | WO1993013664A2 (fr) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0780394A1 (fr) * | 1995-12-20 | 1997-06-25 | Novartis AG | Microbicides |
WO2000061586A1 (fr) * | 1999-04-08 | 2000-10-19 | Akzo Nobel N.V. | Composes heteroaromatiques bicycliques utiles en tant qu'agonistes de l'hormone luteinisante (lh) |
WO2000073289A1 (fr) * | 1999-05-28 | 2000-12-07 | Bayer Aktiengesellschaft | Alpha-phenyl-beta-cetosulfones |
US6706740B2 (en) | 1999-07-20 | 2004-03-16 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
EP1493733A3 (fr) * | 1999-08-20 | 2005-01-26 | Dow AgroSciences LLC | Amides hétérocycliques aromatiques fongicides, leurs compositions et mode d'emploi |
WO2005034950A1 (fr) * | 2003-10-10 | 2005-04-21 | Vernalis (Cambridge) Limited | Composes de pyridothiophene |
WO2006068618A1 (fr) * | 2004-12-23 | 2006-06-29 | Astrazeneca Ab | Nouveaux composés |
WO2006119820A1 (fr) * | 2005-05-12 | 2006-11-16 | Henkel Kommanditgesellschaft Auf Aktien | Agents pour colorer des fibres à base de kératine |
WO2007103308A2 (fr) | 2006-03-07 | 2007-09-13 | Array Biopharma Inc. | Dérivés hétérobicycliques de pyrazole et méthodes d'utilisation |
USRE39991E1 (en) | 1999-08-20 | 2008-01-01 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
JP2008523087A (ja) * | 2004-12-07 | 2008-07-03 | アボット・ラボラトリーズ | バニロイド受容体サブタイプ1(vr1)を抑制するチエノピリジル化合物およびこの使用 |
JP2008533019A (ja) * | 2005-03-09 | 2008-08-21 | シェーリング コーポレイション | Kspキネシン活性を阻害するための化合物 |
WO2009042607A1 (fr) | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Composés inhibiteurs de la pi3k à base de thiazolopyrimidine |
US7521473B2 (en) | 2004-02-25 | 2009-04-21 | Wyeth | Inhibitors of protein tyrosine phosphatase 1B |
WO2009107850A2 (fr) | 2008-02-26 | 2009-09-03 | Takeda Pharmaceutical Company Limited | Dérivé hétérocyclique fusionné et son utilisation |
WO2010105008A2 (fr) | 2009-03-12 | 2010-09-16 | Genentech, Inc. | Combinaisons de composés inhibiteurs de phosphoinositide 3-kinase et d'agents chimiothérapeutiques pour le traitement de tumeurs malignes hématopoïétiques |
WO2010138589A1 (fr) | 2009-05-27 | 2010-12-02 | Genentech, Inc. | Composés pyrimidines bicycliques inhibiteurs de pi3k sélectifs pour p110 delta, et procédés d'utilisation |
WO2011130654A1 (fr) | 2010-04-16 | 2011-10-20 | Genentech, Inc. | Foxo3a utilisée comme biomarqueur prédictif pour l'efficacité d'un inhibiteur de la voie des kinases p13k/akt |
US8133998B2 (en) | 2007-05-09 | 2012-03-13 | Zalicus Pharmaceuticals, Ltd. | Bicyclic pyrimidine derivatives as calcium channel blockers |
WO2012088254A1 (fr) | 2010-12-22 | 2012-06-28 | Genentech, Inc. | Polythérapie par inducteur et inhibiteur d'autophagie pour le traitement de néoplasmes |
JP2012519691A (ja) * | 2009-03-04 | 2012-08-30 | イデニク プハルマセウティカルス,インコーポレイテッド | ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 |
EP2518074A1 (fr) | 2006-12-07 | 2012-10-31 | F. Hoffmann-La Roche AG | Composés inhibiteurs de phosphoinositide 3-kinase et procédés d'utilisation |
WO2014130923A2 (fr) | 2013-02-25 | 2014-08-28 | Genentech, Inc. | Procédés et compositions pour détecter et traiter un mutant d'akt résistant aux médicaments |
CN113943308A (zh) * | 2021-12-09 | 2022-01-18 | 中国科学院新疆理化技术研究所 | 一种三环嘧啶类衍生物及用途 |
US11690847B2 (en) | 2016-11-30 | 2023-07-04 | Case Western Reserve University | Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof |
US11718589B2 (en) | 2017-02-06 | 2023-08-08 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase |
-
1993
- 1993-01-08 WO PCT/GB1993/000029 patent/WO1993013664A2/fr active Application Filing
- 1993-01-08 AU AU32625/93A patent/AU3262593A/en not_active Withdrawn
Cited By (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5814629A (en) * | 1995-12-20 | 1998-09-29 | Novartis Finance Corporation | Microbicides |
EP0780394A1 (fr) * | 1995-12-20 | 1997-06-25 | Novartis AG | Microbicides |
WO2000061586A1 (fr) * | 1999-04-08 | 2000-10-19 | Akzo Nobel N.V. | Composes heteroaromatiques bicycliques utiles en tant qu'agonistes de l'hormone luteinisante (lh) |
US6569863B1 (en) | 1999-04-08 | 2003-05-27 | Akzo Nobel Nv | Bicyclic heteroamatic compounds useful as LH agonists |
US6841553B2 (en) | 1999-04-08 | 2005-01-11 | Akzo Nobel N.V. | Bicyclic heteroaromatic compounds useful as LH agonists |
US6849744B2 (en) | 1999-05-28 | 2005-02-01 | Bayer Aktiengesellschaft | α-phenyl-β-keto sulfones |
WO2000073289A1 (fr) * | 1999-05-28 | 2000-12-07 | Bayer Aktiengesellschaft | Alpha-phenyl-beta-cetosulfones |
US6670385B1 (en) | 1999-05-28 | 2003-12-30 | Bayer Aktiengesellschaft | α-phenyl-βketosulfone |
US6706740B2 (en) | 1999-07-20 | 2004-03-16 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
EP1493733A3 (fr) * | 1999-08-20 | 2005-01-26 | Dow AgroSciences LLC | Amides hétérocycliques aromatiques fongicides, leurs compositions et mode d'emploi |
USRE39991E1 (en) | 1999-08-20 | 2008-01-01 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
WO2005034950A1 (fr) * | 2003-10-10 | 2005-04-21 | Vernalis (Cambridge) Limited | Composes de pyridothiophene |
US7521473B2 (en) | 2004-02-25 | 2009-04-21 | Wyeth | Inhibitors of protein tyrosine phosphatase 1B |
US8501769B2 (en) | 2004-12-07 | 2013-08-06 | Abbvie Inc. | Thienopyridyl compounds that inhibit vanilloid receptor subtype 1 (VR1) and uses thereof |
JP2008523087A (ja) * | 2004-12-07 | 2008-07-03 | アボット・ラボラトリーズ | バニロイド受容体サブタイプ1(vr1)を抑制するチエノピリジル化合物およびこの使用 |
WO2006068618A1 (fr) * | 2004-12-23 | 2006-06-29 | Astrazeneca Ab | Nouveaux composés |
JP2008533019A (ja) * | 2005-03-09 | 2008-08-21 | シェーリング コーポレイション | Kspキネシン活性を阻害するための化合物 |
WO2006119820A1 (fr) * | 2005-05-12 | 2006-11-16 | Henkel Kommanditgesellschaft Auf Aktien | Agents pour colorer des fibres à base de kératine |
WO2007103308A2 (fr) | 2006-03-07 | 2007-09-13 | Array Biopharma Inc. | Dérivés hétérobicycliques de pyrazole et méthodes d'utilisation |
EP2518074A1 (fr) | 2006-12-07 | 2012-10-31 | F. Hoffmann-La Roche AG | Composés inhibiteurs de phosphoinositide 3-kinase et procédés d'utilisation |
US8133998B2 (en) | 2007-05-09 | 2012-03-13 | Zalicus Pharmaceuticals, Ltd. | Bicyclic pyrimidine derivatives as calcium channel blockers |
WO2009042607A1 (fr) | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Composés inhibiteurs de la pi3k à base de thiazolopyrimidine |
US8217176B2 (en) | 2008-02-26 | 2012-07-10 | Takeda Pharmaceutical Company Limited | Fused heterocyclic derivative and use thereof |
US8399449B2 (en) | 2008-02-26 | 2013-03-19 | Takeda Pharmaceutical Company Limited | Fused heterocyclic derivative and use thereof |
WO2009107850A2 (fr) | 2008-02-26 | 2009-09-03 | Takeda Pharmaceutical Company Limited | Dérivé hétérocyclique fusionné et son utilisation |
JP2012519691A (ja) * | 2009-03-04 | 2012-08-30 | イデニク プハルマセウティカルス,インコーポレイテッド | ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 |
WO2010105008A2 (fr) | 2009-03-12 | 2010-09-16 | Genentech, Inc. | Combinaisons de composés inhibiteurs de phosphoinositide 3-kinase et d'agents chimiothérapeutiques pour le traitement de tumeurs malignes hématopoïétiques |
WO2010138589A1 (fr) | 2009-05-27 | 2010-12-02 | Genentech, Inc. | Composés pyrimidines bicycliques inhibiteurs de pi3k sélectifs pour p110 delta, et procédés d'utilisation |
WO2011130654A1 (fr) | 2010-04-16 | 2011-10-20 | Genentech, Inc. | Foxo3a utilisée comme biomarqueur prédictif pour l'efficacité d'un inhibiteur de la voie des kinases p13k/akt |
WO2012088254A1 (fr) | 2010-12-22 | 2012-06-28 | Genentech, Inc. | Polythérapie par inducteur et inhibiteur d'autophagie pour le traitement de néoplasmes |
WO2014130923A2 (fr) | 2013-02-25 | 2014-08-28 | Genentech, Inc. | Procédés et compositions pour détecter et traiter un mutant d'akt résistant aux médicaments |
US11690847B2 (en) | 2016-11-30 | 2023-07-04 | Case Western Reserve University | Combinations of 15-PGDH inhibitors with corticosteroids and/or TNF inhibitors and uses thereof |
US11718589B2 (en) | 2017-02-06 | 2023-08-08 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase |
CN113943308A (zh) * | 2021-12-09 | 2022-01-18 | 中国科学院新疆理化技术研究所 | 一种三环嘧啶类衍生物及用途 |
CN113943308B (zh) * | 2021-12-09 | 2023-11-10 | 中国科学院新疆理化技术研究所 | 一种三环嘧啶类衍生物及用途 |
Also Published As
Publication number | Publication date |
---|---|
AU3262593A (en) | 1993-08-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1993013664A2 (fr) | Composes fongicides biheterocycliques | |
EP0982992B1 (fr) | Utilisation de thienopyrimidines comme fongicides | |
EP0717743B1 (fr) | HERBICIDES AU N-ARYL 1,2,4]triazolo 1,5-a]pyridine-2-sulfonamide | |
JP4215824B2 (ja) | N―([1,2,4]トリアゾロアジニル)ベンゼンスルホンアミド及びピリジンスルホンアミド化合物及び除草剤としてのそれらの利用 | |
AU733431B2 (en) | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides | |
EP0750611A1 (fr) | Derives d'anilide utilises comme fongicides | |
EP0794950A1 (fr) | Derives de l'acide anthranilique utiles en tant que fongicides | |
WO1998042698A1 (fr) | Derives de pyrazole en tant qu'herbicides | |
EP1124827B1 (fr) | Composes 3-(substitues phenyle)-5-(substitues heterocyclyle)-1,2, 4-triazole | |
KR900004996B1 (ko) | 디히드로 이미다조피롤로피리딘류 및 그의 유도체 | |
EP1330458B1 (fr) | Composes de n-( 1,2,4 triazoloazinyl)thiophenesulfonamide comme herbicides | |
CA1256439A (fr) | Imidazolidinones et imidazolidine-thiones; methode et produits intermediaires pour les preparer, leur utilisation comme herbicides | |
US3564606A (en) | 3-amino-5-halogenated aryloxymethyl-1,2,4-oxadiazoles | |
WO2010069494A1 (fr) | Utilisation de 5-pyridine-4-yl(1,3)thiazoles pour la lutte contre les champignons phytopathogènes | |
JP5738978B2 (ja) | 二環式ピリジニルピラゾール類 | |
US5098462A (en) | Substituted semi-carbazones and related compounds | |
EP0606228B1 (fr) | Derives d'acide propenoique | |
US4189483A (en) | Pesticidal compounds, compositions and processes | |
AU2012320581A1 (en) | Heterocyclylpyri (mi) dinylpyrazole as fungicidals | |
KR980009261A (ko) | 1,2,3-벤조티아디아졸 유도체 | |
EP2161259A1 (fr) | 4-haloalkyle-diaminopyrimidines substitués | |
DE3818541A1 (de) | Neue substituierte imidazolone mit herbizider wirkung |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AU BG BR CA FI HU JP KR NO NZ PL RO RU SD UA US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
122 | Ep: pct app. not ent. europ. phase | ||
NENP | Non-entry into the national phase in: |
Ref country code: CA |