AU2009206522B2 - Fungicidal amides - Google Patents
Fungicidal amides Download PDFInfo
- Publication number
- AU2009206522B2 AU2009206522B2 AU2009206522A AU2009206522A AU2009206522B2 AU 2009206522 B2 AU2009206522 B2 AU 2009206522B2 AU 2009206522 A AU2009206522 A AU 2009206522A AU 2009206522 A AU2009206522 A AU 2009206522A AU 2009206522 B2 AU2009206522 B2 AU 2009206522B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- independently
- pct
- ring
- compound
- 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.)
- Ceased
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- 230000000855 fungicidal effect Effects 0.000 title claims description 93
- 150000001408 amides Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 412
- -1 cyano, hydroxy Chemical group 0.000 claims description 240
- 239000000417 fungicide Substances 0.000 claims description 226
- 239000000203 mixture Substances 0.000 claims description 112
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 100
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 31
- 150000001204 N-oxides Chemical class 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 239000003085 diluting agent Substances 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 21
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 14
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 8
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 8
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 241000233654 Oomycetes Species 0.000 claims description 7
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 5
- 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 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 4
- 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 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- 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 claims description 2
- 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
- QWJXAWWCZNATCY-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)piperidine-1-carboxamide Chemical compound CC1=CC=C(C)C(C2N(CCCC2)C(N)=O)=C1 QWJXAWWCZNATCY-UHFFFAOYSA-N 0.000 claims description 2
- NDDLYBISMAOQOM-UHFFFAOYSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[5-(2-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 NDDLYBISMAOQOM-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
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 2
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000009471 action Effects 0.000 description 65
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 241000196324 Embryophyta Species 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 33
- 150000001412 amines Chemical class 0.000 description 30
- 241000233866 Fungi Species 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- 229920000728 polyester Polymers 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000009472 formulation Methods 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 230000012010 growth Effects 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 21
- 239000000047 product 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
- 239000000243 solution Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 125000000304 alkynyl group Chemical group 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 125000000232 haloalkynyl group Chemical group 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 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 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000007429 general method Methods 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 11
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 9
- 101150065749 Churc1 gene Proteins 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102100038239 Protein Churchill Human genes 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 150000001299 aldehydes Chemical group 0.000 description 8
- 230000003115 biocidal effect Effects 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000002538 fungal effect Effects 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000009466 transformation Effects 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-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
- 150000001298 alcohols Chemical group 0.000 description 7
- 125000003302 alkenyloxy group Chemical group 0.000 description 7
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- 230000009974 thixotropic effect Effects 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 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 compound 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
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 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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- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 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
- 108010013280 ubiquinol oxidase Proteins 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- 229940045145 uridine Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 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 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
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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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU2009206522A1 AU2009206522A1 (en) | 2009-07-30 |
| AU2009206522B2 true AU2009206522B2 (en) | 2013-12-19 |
Family
ID=40791146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009206522A Ceased AU2009206522B2 (en) | 2008-01-25 | 2009-01-22 | Fungicidal amides |
Country Status (9)
| Country | Link |
|---|---|
| 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=) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| US8349870B2 (en) | 2008-01-25 | 2013-01-08 | E I Du Pont De Nemours And Company | Fungicidal hetercyclic compounds |
| AU2009322486A1 (en) | 2008-12-02 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| CN102292334A (zh) | 2008-12-11 | 2011-12-21 | 拜尔农作物科学股份公司 | 噻唑基肟醚和腙植物保护剂 |
| US20100267706A1 (en) * | 2009-04-20 | 2010-10-21 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Pyridazine Derivatives |
| US8927551B2 (en) | 2009-05-18 | 2015-01-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US9149465B2 (en) | 2009-05-18 | 2015-10-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| KR20120101019A (ko) | 2009-10-30 | 2012-09-12 | 바이엘 크롭사이언스 아게 | 헤테로아릴피페리딘 및 -피페라진 유도체 |
| MX2012007200A (es) * | 2009-12-21 | 2012-07-10 | Bayer Cropscience Ag | Bis(difluorometil)pirazoles como fungicidas. |
| BR112012016733A2 (pt) * | 2010-01-07 | 2015-09-01 | Du Pont | "composto, composição fungicida e método" |
| BR112012027762B1 (pt) | 2010-04-28 | 2018-06-05 | Bayer Intellectual Property Gmbh | Derivados de cetoheteroarilpiperidina e - piperazina como fungicidas |
| US8815775B2 (en) | 2010-05-18 | 2014-08-26 | Bayer Cropscience Ag | Bis(difluoromethyl)pyrazoles as fungicides |
| BR112012026708A2 (pt) | 2010-05-20 | 2015-09-22 | Du Pont | composto selecionado, composição fungicida e método para controlar doenças vegetais |
| EP2576539B1 (de) | 2010-05-27 | 2017-12-13 | Bayer CropScience AG | Pyridinylcarbonsäure derivate als fungizide |
| US20120122928A1 (en) | 2010-08-11 | 2012-05-17 | 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 |
| US8759527B2 (en) | 2010-08-25 | 2014-06-24 | 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 |
| EP2632922B1 (de) | 2010-10-27 | 2019-02-27 | Bayer CropScience Aktiengesellschaft | Heteroarylpiperidin und -piperazinderivate als fungizide |
| CN103384470A (zh) * | 2010-12-17 | 2013-11-06 | 纳幕尔杜邦公司 | 杀真菌偶氮环酰胺 |
| WO2012104273A1 (de) | 2011-02-01 | 2012-08-09 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| EP2532233A1 (en) | 2011-06-07 | 2012-12-12 | Bayer CropScience AG | Active compound combinations |
| US10004232B2 (en) | 2011-09-15 | 2018-06-26 | Bayer Intellectual Property Gmbh | Piperidine pyrazoles as fungicides |
| DK2797899T3 (en) | 2011-12-27 | 2016-04-04 | Bayer Ip Gmbh | Heteroarylpiperidin and -piperazinderivater as fungicides |
| US9266876B2 (en) | 2012-02-02 | 2016-02-23 | Actelion Pharmaceuticals Ltd. | 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives |
| MX360174B (es) | 2012-02-27 | 2018-10-12 | Bayer Ip Gmbh | Combinaciones de compuestos activos que contienen una tiazolilisoxazolina y un fungicida. |
| MX355542B (es) | 2012-08-30 | 2018-04-20 | Bayer Cropscience Ag | Procedimiento de descarboxilacion de derivados de acido 3,5-bis(haloalquil)-pirazol-4-carboxilico. |
| WO2014054635A1 (ja) * | 2012-10-02 | 2014-04-10 | 大日本住友製薬株式会社 | イミダゾール誘導体 |
| EP2801575A1 (en) | 2013-05-07 | 2014-11-12 | Bayer CropScience AG | Heteroaryldihydropyridine derivatives as fungicides |
| WO2014206896A1 (en) * | 2013-06-24 | 2014-12-31 | Bayer Cropscience Ag | Piperidinecarboxylic acid derivatives as fungicides |
| EA030067B1 (ru) | 2013-07-22 | 2018-06-29 | Идорсиа Фармасьютиклз Лтд | Производные 1-(пиперазин-1-ил)-2-([1,2,4]триазол-1-ил)этанона |
| US9924721B2 (en) | 2013-08-28 | 2018-03-27 | Bayer Cropscience Aktiengesellschaft | Malonic ester derivatives of heteroarylpiperidines and -piperazines as fungicides |
| AR099789A1 (es) | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
| PT3122746T (pt) | 2014-03-24 | 2018-07-27 | Bayer Cropscience Ag | Derivados de fenilpiperidinacarboxamida como fungicidas |
| TWI665192B (zh) * | 2014-05-28 | 2019-07-11 | 德商拜耳作物科學股份有限公司 | 製備二氫異唑衍生物之方法 |
| WO2015181097A1 (en) * | 2014-05-28 | 2015-12-03 | Bayer Cropscience Ag | Process for preparing thiazole derivatives |
| MX380241B (es) | 2014-06-11 | 2025-03-12 | Bayer Cropscience Ag | Proceso para preparar 3-cloro-2-vinilfenol. |
| JP6603242B2 (ja) | 2014-06-11 | 2019-11-06 | 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 | ピペリジン−４−カルボチオアミドの製造 |
| WO2016024350A1 (ja) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | 縮合１１員環化合物及びそれらを含有する農園芸用殺菌剤 |
| JP6337218B2 (ja) | 2015-01-15 | 2018-06-06 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｃｘｃｒ３受容体調節剤としてのヒドロキシアルキル−ピペラジン誘導体 |
| AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
| ES2712915T3 (es) | 2015-03-05 | 2019-05-16 | Bayer Cropscience Ag | Procedimiento para la preparación de clorhidrato de piperidina-4-carbotioamida |
| EP3265446B1 (en) | 2015-03-05 | 2019-08-14 | Bayer CropScience Aktiengesellschaft | Process for preparing substituted phenylisoxazoline derivatives |
| WO2016202761A1 (en) | 2015-06-17 | 2016-12-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| KR102605762B1 (ko) | 2016-02-08 | 2023-11-27 | 고완 크롭 프로텍션 리미티드 | 살균성 조성물 |
| CN108602765B (zh) | 2016-02-08 | 2022-05-03 | 高文有限公司 | 1,2-苯二甲醇化合物的制造方法 |
| TW201838974A (zh) | 2017-04-19 | 2018-11-01 | 印度商Ｐｉ工業公司 | 具殺菌性質之雜環化合物 |
| CN109456317A (zh) * | 2017-09-06 | 2019-03-12 | 华中师范大学 | 含环丙基的化合物及其制备方法和应用以及杀菌剂 |
| WO2019048988A1 (en) | 2017-09-08 | 2019-03-14 | Pi Industries Ltd. | Novel fungidal heterocyclic compounds |
| CA3073637A1 (en) | 2017-09-08 | 2019-03-14 | Pi Industries Ltd | Novel fungicidal heterocyclic compounds |
| WO2021028421A1 (de) | 2019-08-13 | 2021-02-18 | Bayer Aktiengesellschaft | Substituierte 5-(2-heteroaryloxyphenyl)isoxazoline sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| GB201916676D0 (en) * | 2019-11-15 | 2020-01-01 | Syngenta Crop Protection Ag | Improvements in or relating to organic compounds |
| CN113185509A (zh) * | 2020-04-17 | 2021-07-30 | 华中师范大学 | 一种含吲哚环结构的化合物及其制备方法和应用、一种杀菌剂 |
| TW202236965A (zh) | 2020-12-15 | 2022-10-01 | 印度商皮埃企業有限公司 | 包含哌啶噻唑化合物之新穎農業化學組成物 |
| AR125834A1 (es) | 2021-05-15 | 2023-08-16 | Pi Industries Ltd | Composición agroquímica que comprende compuestos de piperidin-tiazol |
| CN115594670B (zh) * | 2021-06-28 | 2025-07-04 | 浙江省化工研究院有限公司 | 一类含三氟甲基噁二唑类衍生物、其制备方法及应用 |
| CN116199683A (zh) * | 2021-11-30 | 2023-06-02 | 江苏中旗科技股份有限公司 | 一种含有噁二唑结构的化合物及其制备方法和应用以及一种杀菌剂 |
| CN116655592A (zh) * | 2022-02-17 | 2023-08-29 | 顺毅南通化工有限公司 | 一种氟噻唑吡乙酮的中间体的制备方法 |
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| WO2005087765A1 (en) * | 2004-03-04 | 2005-09-22 | Arena Pharmaceuticals, Inc. | Ligands of follicle stimulating hormone receptor and methods of use thereof |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| TWI428091B (zh) * | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
-
2009
- 2009-01-22 EP EP09703779A patent/EP2238133A2/en not_active Withdrawn
- 2009-01-22 KR KR1020107018518A patent/KR20100105890A/ko not_active Ceased
- 2009-01-22 WO PCT/US2009/031618 patent/WO2009094407A2/en not_active Ceased
- 2009-01-22 JP JP2010544400A patent/JP5535941B2/ja not_active Expired - Fee Related
- 2009-01-22 CN CN200980102836.XA patent/CN101925598B/zh not_active Expired - Fee Related
- 2009-01-22 MX MX2010007974A patent/MX2010007974A/es active IP Right Grant
- 2009-01-22 US US12/811,126 patent/US20100286147A1/en not_active Abandoned
- 2009-01-22 BR BRPI0905758-7A patent/BRPI0905758A2/pt not_active Application Discontinuation
- 2009-01-22 AU AU2009206522A patent/AU2009206522B2/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005087765A1 (en) * | 2004-03-04 | 2005-09-22 | Arena Pharmaceuticals, Inc. | Ligands of follicle stimulating hormone receptor and methods of use thereof |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2238133A2 (en) | 2010-10-13 |
| WO2009094407A3 (en) | 2009-10-29 |
| MX2010007974A (es) | 2010-08-04 |
| US20100286147A1 (en) | 2010-11-11 |
| WO2009094407A2 (en) | 2009-07-30 |
| KR20100105890A (ko) | 2010-09-30 |
| JP2011510925A (ja) | 2011-04-07 |
| CN101925598B (zh) | 2014-03-05 |
| BRPI0905758A2 (pt) | 2015-07-14 |
| AU2009206522A1 (en) | 2009-07-30 |
| JP5535941B2 (ja) | 2014-07-02 |
| CN101925598A (zh) | 2010-12-22 |
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