AU2011344161A1 - Fungicidal azocyclic amides - Google Patents
Fungicidal azocyclic amides Download PDFInfo
- Publication number
- AU2011344161A1 AU2011344161A1 AU2011344161A AU2011344161A AU2011344161A1 AU 2011344161 A1 AU2011344161 A1 AU 2011344161A1 AU 2011344161 A AU2011344161 A AU 2011344161A AU 2011344161 A AU2011344161 A AU 2011344161A AU 2011344161 A1 AU2011344161 A1 AU 2011344161A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- haloalkyl
- ring
- formula
- independently selected
- 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.)
- Abandoned
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- 230000000855 fungicidal effect Effects 0.000 title claims description 91
- 150000001408 amides Chemical class 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 410
- 239000000417 fungicide Substances 0.000 claims description 244
- 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 240
- -1 cyano, amino Chemical group 0.000 claims description 159
- 239000000203 mixture Substances 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
- 239000001257 hydrogen Substances 0.000 claims description 99
- 229910052736 halogen Inorganic materials 0.000 claims description 95
- 150000002367 halogens Chemical class 0.000 claims description 92
- 125000001424 substituent group Chemical group 0.000 claims description 88
- 150000001721 carbon Chemical group 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 78
- 125000003545 alkoxy group Chemical group 0.000 claims description 76
- 125000001188 haloalkyl group Chemical group 0.000 claims description 72
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000004122 cyclic group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000004429 atom Chemical group 0.000 claims description 34
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 29
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 29
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 28
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 27
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 150000001204 N-oxides Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 15
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 14
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 12
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 claims description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 11
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 11
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 9
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 8
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 8
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 7
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 5
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- 238000007667 floating Methods 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 2
- 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 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims 1
- 125000006771 (C1-C6) haloalkylthio 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
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 1
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 101100248300 Mus musculus Rhbdf2 gene Proteins 0.000 claims 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 1
- 101150113676 chr1 gene Proteins 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 230000009471 action Effects 0.000 description 69
- 239000002253 acid Substances 0.000 description 54
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 52
- 150000001412 amines Chemical class 0.000 description 51
- 125000003342 alkenyl group Chemical group 0.000 description 49
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 47
- 125000000304 alkynyl group Chemical group 0.000 description 46
- 241000196324 Embryophyta Species 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- 238000002360 preparation method Methods 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 241000233866 Fungi Species 0.000 description 31
- 239000002585 base Substances 0.000 description 29
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 238000009472 formulation Methods 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- MNYPIQZZKPKMSN-UHFFFAOYSA-N 5-chloro-3-[3-[3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]propyl]-1,3-benzothiazol-2-one Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(CCCN3C(SC4=CC=C(Cl)C=C43)=O)ON=2)CC1 MNYPIQZZKPKMSN-UHFFFAOYSA-N 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
- 230000012010 growth Effects 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- 235000011181 potassium carbonates Nutrition 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 229930182558 Sterol Natural products 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 235000003702 sterols Nutrition 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000002516 radical scavenger Substances 0.000 description 16
- 150000003432 sterols Chemical class 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 229940125782 compound 2 Drugs 0.000 description 15
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- JWODWKHBAMCDKG-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-2-[3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]acetamide Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(CC(=O)NCC=3C(=CC=CC=3F)F)ON=2)CC1 JWODWKHBAMCDKG-UHFFFAOYSA-N 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 14
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- 229940125773 compound 10 Drugs 0.000 description 13
- 229940126142 compound 16 Drugs 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 238000007429 general method Methods 0.000 description 13
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 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 description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 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
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 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
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-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
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 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
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/72—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
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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 |
|---|---|---|---|
| US201061424228P | 2010-12-17 | 2010-12-17 | |
| US61/424,228 | 2010-12-17 | ||
| PCT/US2011/064324 WO2012082580A2 (en) | 2010-12-17 | 2011-12-12 | Fungicidal azocyclic amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011344161A1 true AU2011344161A1 (en) | 2013-06-20 |
| AU2011344161A2 AU2011344161A2 (en) | 2013-06-27 |
Family
ID=45446208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011344161A Abandoned AU2011344161A1 (en) | 2010-12-17 | 2011-12-12 | Fungicidal azocyclic amides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20130261154A1 (https=) |
| EP (1) | EP2651219A2 (https=) |
| JP (1) | JP2014501246A (https=) |
| KR (1) | KR20140017520A (https=) |
| CN (1) | CN103384470A (https=) |
| AU (1) | AU2011344161A1 (https=) |
| BR (1) | BR112013015166A2 (https=) |
| CL (1) | CL2013001722A1 (https=) |
| MX (1) | MX2013006936A (https=) |
| WO (1) | WO2012082580A2 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009322486A1 (en) * | 2008-12-02 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| PL2651902T3 (pl) | 2010-12-17 | 2018-04-30 | Reata Pharmaceuticals, Inc. | Pirazolilowe i pirymidynylowe tricykliczne enony jako modulatory zapalenia o działaniu przeciwutleniającym |
| CN103282359A (zh) | 2010-12-17 | 2013-09-04 | 诺华股份有限公司 | 5-氯-n2-(2-异丙氧基-5-甲基-4-哌啶-4-基-苯基)-n4-[2-(丙烷-2-磺酰基)-苯基]-嘧啶-2,4-二胺的结晶形式 |
| WO2012104273A1 (de) * | 2011-02-01 | 2012-08-09 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| 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 |
| EP2864326A1 (en) * | 2012-06-22 | 2015-04-29 | E. I. Du Pont de Nemours and Company | Fungicidal heterocyclic compounds |
| EP2801575A1 (en) | 2013-05-07 | 2014-11-12 | Bayer CropScience AG | Heteroaryldihydropyridine derivatives as fungicides |
| US8906951B1 (en) | 2013-06-24 | 2014-12-09 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
| US9198898B2 (en) | 2013-06-24 | 2015-12-01 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
| 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 |
| 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 |
| 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 |
| KR102605762B1 (ko) | 2016-02-08 | 2023-11-27 | 고완 크롭 프로텍션 리미티드 | 살균성 조성물 |
| WO2018071535A1 (en) * | 2016-10-14 | 2018-04-19 | Merial, Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| 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 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| TW202115024A (zh) | 2019-08-14 | 2021-04-16 | 美商英塞特公司 | 作為cdk2 抑制劑之咪唑基嘧啶基胺化合物 |
| AU2020364007A1 (en) | 2019-10-11 | 2022-04-28 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN114644634B (zh) * | 2020-12-21 | 2023-06-20 | 深圳市祥根生物医药有限公司 | 一种吡咯衍生物及其制备方法和用途 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
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| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4089672A (en) | 1972-12-20 | 1978-05-16 | The Upjohn Company | 1-(Substituted-hydrocarbyl)-di- and trihalopyrazoles |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| US4584014A (en) | 1984-07-02 | 1986-04-22 | Rohm And Haas Company | Ethylideneaminooxyacetic acids and esters |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DE69033861T2 (de) | 1989-08-30 | 2002-06-06 | Kynoch Agrochemicals (Proprietary) Ltd., Sandton | Herstellung eines Dosierungsmittels |
| ES2065680T3 (es) | 1990-03-12 | 1995-02-16 | Du Pont | Granulos de plaguicida dispersables en agua o solubles en agua a partir de aglutinantes activados por calor. |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| GB9416364D0 (en) | 1994-08-12 | 1994-10-05 | Fine Organics Ltd | Preparation of thioamides |
| AU2000267381A1 (en) | 2000-08-28 | 2002-03-13 | Korea Research Institute Of Chemical Technology | Resins having vinyl ether linker for the solid phase organic synthesis |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| TW200837064A (en) | 2006-10-04 | 2008-09-16 | Pharmacopeia Inc | 8-substituted 2-(benzimidazolyl)purine derivatives for immunosuppression |
| WO2008103615A1 (en) | 2007-02-21 | 2008-08-28 | Kalypsys, Inc. | Isoquinolines useful as inducible nitric oxide synthase inhibitors |
| TWI428091B (zh) * | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
| EP2238133A2 (en) * | 2008-01-25 | 2010-10-13 | E. I. du Pont de Nemours and Company | Fungicidal amides |
| 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 |
| US20120122928A1 (en) * | 2010-08-11 | 2012-05-17 | Bayer Cropscience Ag | Heteroarylpiperidine and -Piperazine Derivatives as Fungicides |
-
2011
- 2011-12-12 CN CN2011800678071A patent/CN103384470A/zh active Pending
- 2011-12-12 KR KR1020137018596A patent/KR20140017520A/ko not_active Withdrawn
- 2011-12-12 JP JP2013544634A patent/JP2014501246A/ja active Pending
- 2011-12-12 US US13/990,542 patent/US20130261154A1/en not_active Abandoned
- 2011-12-12 AU AU2011344161A patent/AU2011344161A1/en not_active Abandoned
- 2011-12-12 MX MX2013006936A patent/MX2013006936A/es unknown
- 2011-12-12 WO PCT/US2011/064324 patent/WO2012082580A2/en not_active Ceased
- 2011-12-12 BR BR112013015166A patent/BR112013015166A2/pt not_active IP Right Cessation
- 2011-12-12 EP EP11805311.5A patent/EP2651219A2/en not_active Withdrawn
-
2013
- 2013-06-14 CL CL2013001722A patent/CL2013001722A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2651219A2 (en) | 2013-10-23 |
| KR20140017520A (ko) | 2014-02-11 |
| BR112013015166A2 (pt) | 2016-07-12 |
| JP2014501246A (ja) | 2014-01-20 |
| US20130261154A1 (en) | 2013-10-03 |
| WO2012082580A2 (en) | 2012-06-21 |
| WO2012082580A3 (en) | 2013-08-01 |
| MX2013006936A (es) | 2013-07-22 |
| AU2011344161A2 (en) | 2013-06-27 |
| CL2013001722A1 (es) | 2014-04-11 |
| CN103384470A (zh) | 2013-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 30 MAY 2013 |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |