JP5535941B2 - 殺菌性アミド - Google Patents
殺菌性アミド Download PDFInfo
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- JP5535941B2 JP5535941B2 JP2010544400A JP2010544400A JP5535941B2 JP 5535941 B2 JP5535941 B2 JP 5535941B2 JP 2010544400 A JP2010544400 A JP 2010544400A JP 2010544400 A JP2010544400 A JP 2010544400A JP 5535941 B2 JP5535941 B2 JP 5535941B2
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- Japan
- Prior art keywords
- formula
- compound
- alkyl
- fungicides
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 48
- 150000001408 amides Chemical class 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 389
- -1 1 -Methyl-3,5-dioxo-1,2,4-triazolidin-4-yl Chemical group 0.000 claims description 167
- 238000000034 method Methods 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 150000001204 N-oxides Chemical class 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 150000001721 carbon Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 244000000004 fungal plant pathogen Species 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 3
- 241000233654 Oomycetes Species 0.000 claims description 3
- PVDYADKFRYXEGR-UHFFFAOYSA-N 1-[4-[4-[5-[2-fluoro-6-(1,2,4-triazol-1-yl)phenyl]-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 compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)N2N=CN=C2)CC1 PVDYADKFRYXEGR-UHFFFAOYSA-N 0.000 claims description 2
- DCBHAFISNQAOPP-UHFFFAOYSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-(4-phenylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 DCBHAFISNQAOPP-UHFFFAOYSA-N 0.000 claims description 2
- KSKYUOQCQXXQTM-UHFFFAOYSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-[2-(1,2,4-triazol-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)N2N=CN=C2)CC1 KSKYUOQCQXXQTM-UHFFFAOYSA-N 0.000 claims description 2
- RALLPMAZSMMNKM-UHFFFAOYSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-[3-(1,2,4-triazol-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C=C(C=CC=2)N2N=CN=C2)CC1 RALLPMAZSMMNKM-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
- CPHWKUGPGDJWEF-UHFFFAOYSA-N n-(2,5-dimethylphenyl)-4-[4-[5-(2-phenylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboxamide Chemical compound CC1=CC=C(C)C(NC(=O)N2CCC(CC2)C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 CPHWKUGPGDJWEF-UHFFFAOYSA-N 0.000 claims description 2
- YXFRAKAXEGMENR-UHFFFAOYSA-N n-(2,5-dimethylphenyl)-4-[4-[5-[2-(1,2,4-triazol-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboxamide Chemical compound CC1=CC=C(C)C(NC(=O)N2CCC(CC2)C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)N2N=CN=C2)=C1 YXFRAKAXEGMENR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 1
- 239000000417 fungicide Substances 0.000 description 273
- 230000000855 fungicidal effect Effects 0.000 description 126
- 239000000203 mixture Substances 0.000 description 104
- 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 90
- 125000000217 alkyl group Chemical group 0.000 description 68
- 230000009471 action Effects 0.000 description 66
- 125000001424 substituent group Chemical group 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 48
- 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 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 229910052736 halogen Inorganic materials 0.000 description 44
- 241000196324 Embryophyta Species 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 150000002367 halogens Chemical class 0.000 description 41
- 239000003899 bactericide agent Substances 0.000 description 37
- 125000000623 heterocyclic group Chemical group 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 34
- 125000003545 alkoxy group Chemical group 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- 150000001412 amines Chemical class 0.000 description 29
- 239000002585 base Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000009472 formulation Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000007788 liquid Substances 0.000 description 25
- 125000004093 cyano group Chemical group *C#N 0.000 description 24
- 125000004122 cyclic group Chemical group 0.000 description 24
- 125000004663 dialkyl amino group Chemical group 0.000 description 24
- 229910052717 sulfur Inorganic materials 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- 230000012010 growth Effects 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- 241000233866 Fungi Species 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- 239000003085 diluting agent Substances 0.000 description 21
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
- 125000004429 atom Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 17
- 230000002538 fungal effect Effects 0.000 description 17
- 125000005842 heteroatom Chemical group 0.000 description 17
- 229910052740 iodine Inorganic materials 0.000 description 17
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 16
- 125000001188 haloalkyl group Chemical group 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000006467 substitution reaction Methods 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 125000003282 alkyl amino group Chemical group 0.000 description 13
- 125000004438 haloalkoxy group Chemical group 0.000 description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000002619 bicyclic group Chemical group 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 11
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 238000007429 general method Methods 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 230000001954 sterilising effect Effects 0.000 description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 239000000645 desinfectant Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 229930182558 Sterol Natural products 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 230000029058 respiratory gaseous exchange Effects 0.000 description 7
- 150000003432 sterols Chemical class 0.000 description 7
- 235000003702 sterols Nutrition 0.000 description 7
- 150000003871 sulfonates Chemical class 0.000 description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 6
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 6
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- 0 CC(CC=C)(**)SCNC Chemical compound CC(CC=C)(**)SCNC 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 102000029749 Microtubule Human genes 0.000 description 6
- 108091022875 Microtubule Proteins 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 210000004688 microtubule Anatomy 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- YLZGKZDEFJIHIJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl) carbamate Chemical compound C1=CC=C2N(C)C(OC(N)=O)=NC2=C1 YLZGKZDEFJIHIJ-UHFFFAOYSA-N 0.000 description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 5
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 5
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 150000003626 triacylglycerols Chemical class 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical group CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
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- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- PQHXFGUTAAIHOC-XZZSYSLUSA-N α-(methoxyimino)-n-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1\C=N\OC(C)C1=CC=CC(C(F)(F)F)=C1 PQHXFGUTAAIHOC-XZZSYSLUSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
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| US6236708P | 2008-01-25 | 2008-01-25 | |
| US61/062,367 | 2008-01-25 | ||
| PCT/US2009/031618 WO2009094407A2 (en) | 2008-01-25 | 2009-01-22 | Fungicidal amides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510925A JP2011510925A (ja) | 2011-04-07 |
| JP2011510925A5 JP2011510925A5 (https=) | 2012-03-01 |
| JP5535941B2 true JP5535941B2 (ja) | 2014-07-02 |
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| JP2010544400A Expired - Fee Related JP5535941B2 (ja) | 2008-01-25 | 2009-01-22 | 殺菌性アミド |
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|---|---|
| US (1) | US20100286147A1 (https=) |
| EP (1) | EP2238133A2 (https=) |
| JP (1) | JP5535941B2 (https=) |
| KR (1) | KR20100105890A (https=) |
| CN (1) | CN101925598B (https=) |
| AU (1) | AU2009206522B2 (https=) |
| BR (1) | BRPI0905758A2 (https=) |
| MX (1) | MX2010007974A (https=) |
| WO (1) | WO2009094407A2 (https=) |
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| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| US9090604B2 (en) | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| AU2014202324B2 (en) * | 2007-10-23 | 2016-05-19 | Corteva Agriscience Llc | Fungicidal compounds and mixtures |
| TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
| CN101970432B (zh) | 2008-01-25 | 2014-05-28 | 杜邦公司 | 杀真菌杂环化合物 |
| TW201036966A (en) | 2008-12-02 | 2010-10-16 | Du Pont | Fungicidal heterocyclic compounds |
| BRPI0923366A2 (pt) | 2008-12-11 | 2019-09-24 | Bayer Cropscience Ag | éteres e hodrazonas de oxima de tiazolila como agentes protetors de culturas. |
| US20100267706A1 (en) * | 2009-04-20 | 2010-10-21 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Pyridazine Derivatives |
| US9149465B2 (en) | 2009-05-18 | 2015-10-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US8927551B2 (en) | 2009-05-18 | 2015-01-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| EP2493886B1 (de) | 2009-10-30 | 2014-11-26 | Bayer CropScience AG | Heteroarylpiperidin und -piperazin derivate |
| JP5785560B2 (ja) | 2009-12-21 | 2015-09-30 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺真菌剤としてのビス（ジフルオロメチル）ピラゾール |
| KR20120112755A (ko) * | 2010-01-07 | 2012-10-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 살진균제 복소환 화합물 |
| JP5960683B2 (ja) | 2010-04-28 | 2016-08-02 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺真菌剤としてのケトヘテロアリールピペリジンおよび−ピペラジン誘導体 |
| US8815775B2 (en) | 2010-05-18 | 2014-08-26 | Bayer Cropscience Ag | Bis(difluoromethyl)pyrazoles as fungicides |
| EP2571866A1 (en) * | 2010-05-20 | 2013-03-27 | E.I. Du Pont De Nemours And Company | Fungicidal oximes and hydrazones |
| JP2013528169A (ja) | 2010-05-27 | 2013-07-08 | バイエル・クロップサイエンス・アーゲー | 殺菌剤としてのピリジニルカルボン酸誘導体 |
| US20120122928A1 (en) | 2010-08-11 | 2012-05-17 | Bayer Cropscience Ag | Heteroarylpiperidine and -Piperazine Derivatives as Fungicides |
| EP2423210A1 (de) | 2010-08-25 | 2012-02-29 | Bayer CropScience AG | Heteroarylpiperidin- und -piperazinderivate als Fungizide |
| US8759527B2 (en) * | 2010-08-25 | 2014-06-24 | Bayer Cropscience Ag | Heteroarylpiperidine and -piperazine derivatives as fungicides |
| AU2015261660B2 (en) * | 2010-08-25 | 2017-01-05 | Bayer Cropscience Aktiengesellschaft | Heteroarylpiperidine and -piperazine derivatives as fungicides |
| PE20141002A1 (es) | 2010-10-27 | 2014-08-17 | Bayer Ip Gmbh | Derivados de heteroarilpiperidina y -piperazina como fungicidas |
| WO2012082580A2 (en) * | 2010-12-17 | 2012-06-21 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| KR101848116B1 (ko) | 2011-02-01 | 2018-04-11 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 살진균제로서의 헤테로아릴 피페리딘 및 헤테로아릴 피페라진 유도체 |
| EP2532233A1 (en) | 2011-06-07 | 2012-12-12 | Bayer CropScience AG | Active compound combinations |
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| DE19642863A1 (de) * | 1996-10-17 | 1998-04-23 | Bayer Ag | Amide |
| GB0230162D0 (en) * | 2002-12-24 | 2003-02-05 | Metris Therapeutics Ltd | Compounds useful in inhibiting angiogenesis |
| WO2005087765A1 (en) * | 2004-03-04 | 2005-09-22 | Arena Pharmaceuticals, Inc. | Ligands of follicle stimulating hormone receptor and methods of use thereof |
| US7713998B2 (en) * | 2004-11-10 | 2010-05-11 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic compound and pharmaceutical use thereof |
| TW200738701A (en) * | 2005-07-26 | 2007-10-16 | Du Pont | Fungicidal carboxamides |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| TWI428091B (zh) * | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
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| MX2010007974A (es) | 2010-08-04 |
| CN101925598B (zh) | 2014-03-05 |
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| AU2009206522A1 (en) | 2009-07-30 |
| JP2011510925A (ja) | 2011-04-07 |
| KR20100105890A (ko) | 2010-09-30 |
| WO2009094407A3 (en) | 2009-10-29 |
| AU2009206522B2 (en) | 2013-12-19 |
| EP2238133A2 (en) | 2010-10-13 |
| US20100286147A1 (en) | 2010-11-11 |
| BRPI0905758A2 (pt) | 2015-07-14 |
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