TWI428091B - 殺真菌劑混合物 - Google Patents
殺真菌劑混合物 Download PDFInfo
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- TWI428091B TWI428091B TW097137380A TW97137380A TWI428091B TW I428091 B TWI428091 B TW I428091B TW 097137380 A TW097137380 A TW 097137380A TW 97137380 A TW97137380 A TW 97137380A TW I428091 B TWI428091 B TW I428091B
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- 239000000203 mixture Substances 0.000 title claims description 585
- 230000000855 fungicidal effect Effects 0.000 title claims description 240
- 239000000417 fungicide Substances 0.000 title description 304
- 150000001875 compounds Chemical class 0.000 claims description 373
- -1 5-phenyl-3-isoxazolyl Chemical group 0.000 claims description 232
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 97
- 125000003943 azolyl group Chemical group 0.000 claims description 77
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 61
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 39
- 239000007787 solid Substances 0.000 claims description 33
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 18
- 239000004615 ingredient Substances 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 239000005747 Chlorothalonil Substances 0.000 claims description 6
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 6
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims description 6
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 5
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005740 Boscalid Substances 0.000 claims description 5
- 239000005754 Cyazofamid Substances 0.000 claims description 5
- 239000005756 Cymoxanil Substances 0.000 claims description 5
- 239000005802 Mancozeb Substances 0.000 claims description 5
- 239000005804 Mandipropamid Substances 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 5
- 229940118790 boscalid Drugs 0.000 claims description 5
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 claims description 5
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims description 4
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 4
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 4
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 4
- 239000005750 Copper hydroxide Substances 0.000 claims description 4
- 239000005761 Dimethomorph Substances 0.000 claims description 4
- 239000005772 Famoxadone Substances 0.000 claims description 4
- 239000005774 Fenamidone Substances 0.000 claims description 4
- 239000005780 Fluazinam Substances 0.000 claims description 4
- 239000005782 Fluopicolide Substances 0.000 claims description 4
- 239000005789 Folpet Substances 0.000 claims description 4
- 239000005797 Iprovalicarb Substances 0.000 claims description 4
- 239000005800 Kresoxim-methyl Substances 0.000 claims description 4
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 claims description 4
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005816 Penthiopyrad Substances 0.000 claims description 4
- 239000005824 Proquinazid Substances 0.000 claims description 4
- 239000005831 Quinoxyfen Substances 0.000 claims description 4
- 239000005857 Trifloxystrobin Substances 0.000 claims description 4
- 239000005860 Valifenalate Substances 0.000 claims description 4
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 4
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 claims description 4
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 4
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 claims description 4
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 4
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 claims description 4
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 claims description 4
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 claims description 4
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 claims description 4
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000005821 Propamocarb Substances 0.000 claims description 2
- 239000005869 Pyraclostrobin Substances 0.000 claims description 2
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 2
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims description 2
- IAQLCKZJGNTRDO-LJQANCHMSA-N (R)-oxathiapiprolin Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-LJQANCHMSA-N 0.000 claims 1
- QWZOUWNYDSVFLX-LJQANCHMSA-N 1-[4-[4-[(5r)-5-(2,6-dichlorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2Cl)Cl)CC1 QWZOUWNYDSVFLX-LJQANCHMSA-N 0.000 claims 1
- BGLGDZFPJHFWEZ-OAQYLSRUSA-N 1-[4-[4-[(5r)-5-(2,6-dimethylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2C)C)CC1 BGLGDZFPJHFWEZ-OAQYLSRUSA-N 0.000 claims 1
- HFSOCJMWHBUPMW-HXUWFJFHSA-N 1-[4-[4-[(5r)-5-(2-fluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2)F)CC1 HFSOCJMWHBUPMW-HXUWFJFHSA-N 0.000 claims 1
- FACIKTWBHFNWON-OAQYLSRUSA-N 1-[4-[4-[(5r)-5-(2-methylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2)C)CC1 FACIKTWBHFNWON-OAQYLSRUSA-N 0.000 claims 1
- HFGIAJCHFQMGKC-XMMPIXPASA-N 1-[4-[4-[(5r)-5-methyl-5-phenyl-4h-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@](C)(ON=2)C=2C=CC=CC=2)CC1 HFGIAJCHFQMGKC-XMMPIXPASA-N 0.000 claims 1
- POYLZDKZCBQQKF-HXUWFJFHSA-N 2-[3-methyl-5-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical class N1=C(C)C=C(C(F)(F)F)N1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C=CC=CC=2)CC1 POYLZDKZCBQQKF-HXUWFJFHSA-N 0.000 claims 1
- USWYPSPVHHMZPH-HSZRJFAPSA-N 2-[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-methyl-5-phenyl-4h-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical class C([C@](ON=1)(C)C=2C=CC=CC=2)C=1C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1Cl USWYPSPVHHMZPH-HSZRJFAPSA-N 0.000 claims 1
- ZSZAMVYEGDWEDY-OAQYLSRUSA-N 2-[5-ethyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical class CCC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C=CC=CC=2)CC1 ZSZAMVYEGDWEDY-OAQYLSRUSA-N 0.000 claims 1
- VRFDJVDIZBADRD-JOCHJYFZSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-(2,4,6-trimethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical class COC1=CC(OC)=CC(OC)=C1[C@@H]1ON=C(C=2N=C(SC=2)C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)C1 VRFDJVDIZBADRD-JOCHJYFZSA-N 0.000 claims 1
- CLRPPJBUFODHQQ-JOCHJYFZSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-(2,4,6-trimethylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical class CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC(C)=CC=2C)C)CC1 CLRPPJBUFODHQQ-JOCHJYFZSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 154
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
- 239000011541 reaction mixture Substances 0.000 description 101
- 125000001424 substituent group Chemical group 0.000 description 97
- 229910052799 carbon Inorganic materials 0.000 description 78
- 239000000243 solution Substances 0.000 description 69
- 238000002360 preparation method Methods 0.000 description 68
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 125000004122 cyclic group Chemical group 0.000 description 53
- 229910052736 halogen Inorganic materials 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- 125000000217 alkyl group Chemical group 0.000 description 51
- 238000000034 method Methods 0.000 description 50
- 229940126214 compound 3 Drugs 0.000 description 49
- 150000002367 halogens Chemical class 0.000 description 47
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 150000003839 salts Chemical class 0.000 description 44
- 125000000623 heterocyclic group Chemical group 0.000 description 43
- 230000002829 reductive effect Effects 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 150000001412 amines Chemical class 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- 125000004429 atom Chemical group 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 38
- 125000004093 cyano group Chemical group *C#N 0.000 description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 35
- 125000001072 heteroaryl group Chemical group 0.000 description 35
- 229910052717 sulfur Inorganic materials 0.000 description 32
- 125000005842 heteroatom Chemical group 0.000 description 31
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- 229920006395 saturated elastomer Polymers 0.000 description 29
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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- 230000015572 biosynthetic process Effects 0.000 description 25
- 229910052760 oxygen Inorganic materials 0.000 description 25
- 150000001204 N-oxides Chemical class 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 22
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 20
- 230000012010 growth Effects 0.000 description 20
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 19
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 125000004430 oxygen atom Chemical group O* 0.000 description 18
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 16
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 16
- 125000004663 dialkyl amino group Chemical group 0.000 description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 15
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- 201000010099 disease Diseases 0.000 description 15
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- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 13
- 101150065749 Churc1 gene Proteins 0.000 description 13
- 102100038239 Protein Churchill Human genes 0.000 description 13
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US207P | 2007-10-23 | 2007-10-23 | |
| US6240008P | 2008-01-25 | 2008-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200917963A TW200917963A (en) | 2009-05-01 |
| TWI428091B true TWI428091B (zh) | 2014-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097137380A TWI428091B (zh) | 2007-10-23 | 2008-09-26 | 殺真菌劑混合物 |
Country Status (38)
Families Citing this family (158)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9090604B2 (en) | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| EP2070413A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
| CN101970432B (zh) | 2008-01-25 | 2014-05-28 | 杜邦公司 | 杀真菌杂环化合物 |
| JP5535941B2 (ja) * | 2008-01-25 | 2014-07-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性アミド |
| DE102008001932A1 (de) * | 2008-05-21 | 2009-11-26 | Bayer Cropscience Ag | Substiuierte Spiroisoxazoline |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| BRPI0917394A2 (pt) * | 2008-08-18 | 2019-09-24 | Univ Yale | moduladores de mif |
| WO2010037479A1 (de) | 2008-10-01 | 2010-04-08 | Bayer Cropscience Ag | Heterocyclyl substituierte thiazole als pflanzenschutzmittel |
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