AU2011256730B2 - Fungicidal oximes and hydrazones - Google Patents
Fungicidal oximes and hydrazones Download PDFInfo
- Publication number
- AU2011256730B2 AU2011256730B2 AU2011256730A AU2011256730A AU2011256730B2 AU 2011256730 B2 AU2011256730 B2 AU 2011256730B2 AU 2011256730 A AU2011256730 A AU 2011256730A AU 2011256730 A AU2011256730 A AU 2011256730A AU 2011256730 B2 AU2011256730 B2 AU 2011256730B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- fungicides
- alkyl
- methyl
- 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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- 230000000855 fungicidal effect Effects 0.000 title claims description 92
- 150000002923 oximes Chemical class 0.000 title description 13
- 150000007857 hydrazones Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 492
- 239000000417 fungicide Substances 0.000 claims description 245
- 239000000203 mixture Substances 0.000 claims description 129
- 238000000034 method Methods 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 49
- 150000002367 halogens Chemical class 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 34
- 201000010099 disease Diseases 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 31
- 239000007787 solid Substances 0.000 claims description 29
- 239000003085 diluting agent Substances 0.000 claims description 27
- 150000001204 N-oxides Chemical class 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- 239000004094 surface-active agent Substances 0.000 claims description 23
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 9
- 244000000004 fungal plant pathogen Species 0.000 claims description 7
- YMPJINKZPMDWLR-UHFFFAOYSA-N 1-[4-[4-[c-[2-(2,6-difluorophenyl)-2-hydroxyethyl]-n-hydroxycarbonimidoyl]-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(CC(O)C=2C(=CC=CC=2F)F)=NO)CC1 YMPJINKZPMDWLR-UHFFFAOYSA-N 0.000 claims description 3
- SCTAWEVXLMZZSI-UHFFFAOYSA-N 1-[4-[4-[c-[2-(2,6-difluorophenyl)ethenyl]-n-methoxycarbonimidoyl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(=NOC)C=CC1=C(F)C=CC=C1F SCTAWEVXLMZZSI-UHFFFAOYSA-N 0.000 claims description 3
- RLSJXLGPFNBKDJ-UHFFFAOYSA-N [[3-(2,6-difluorophenyl)-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]prop-2-enylidene]amino] acetate Chemical compound C=1SC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=NC=1C(=NOC(=O)C)C=CC1=C(F)C=CC=C1F RLSJXLGPFNBKDJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- -1 cyano, amino Chemical group 0.000 description 123
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
- 125000000217 alkyl group Chemical group 0.000 description 81
- 125000001424 substituent group Chemical group 0.000 description 75
- 230000009471 action Effects 0.000 description 69
- 125000004093 cyano group Chemical group *C#N 0.000 description 64
- 229910052739 hydrogen Inorganic materials 0.000 description 61
- 239000001257 hydrogen Substances 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 54
- 125000003545 alkoxy group Chemical group 0.000 description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
- 241000196324 Embryophyta Species 0.000 description 45
- 125000001188 haloalkyl group Chemical group 0.000 description 45
- 239000002253 acid Substances 0.000 description 44
- 150000001412 amines Chemical class 0.000 description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 238000002360 preparation method Methods 0.000 description 42
- 125000003342 alkenyl group Chemical group 0.000 description 41
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 41
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 40
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 39
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 39
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 39
- 229910052799 carbon Inorganic materials 0.000 description 39
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 description 39
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 38
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 38
- 125000000304 alkynyl group Chemical group 0.000 description 38
- 229940126208 compound 22 Drugs 0.000 description 38
- 229940125833 compound 23 Drugs 0.000 description 38
- 150000001721 carbon Chemical group 0.000 description 37
- 125000000623 heterocyclic group Chemical group 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 125000001309 chloro group Chemical group Cl* 0.000 description 34
- 125000000753 cycloalkyl group Chemical group 0.000 description 33
- 125000001072 heteroaryl group Chemical group 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 241000233866 Fungi Species 0.000 description 31
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 31
- 125000000262 haloalkenyl group Chemical group 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 29
- 125000000232 haloalkynyl group Chemical group 0.000 description 29
- 125000005842 heteroatom Chemical group 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 28
- 125000004122 cyclic group Chemical group 0.000 description 27
- 125000001624 naphthyl group Chemical group 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 230000012010 growth Effects 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 22
- 125000004429 atom Chemical group 0.000 description 22
- 239000002585 base Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 125000004438 haloalkoxy group Chemical group 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000012360 testing method Methods 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 229930182558 Sterol Natural products 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 17
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 17
- 235000003702 sterols Nutrition 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 16
- 150000003432 sterols Chemical class 0.000 description 16
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 15
- 125000004663 dialkyl amino group Chemical group 0.000 description 15
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000005347 halocycloalkyl group Chemical group 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- 239000002516 radical scavenger Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000002837 carbocyclic group Chemical group 0.000 description 12
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 230000002538 fungal effect Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 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 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 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
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 description 10
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 238000007429 general method Methods 0.000 description 9
- 150000002576 ketones Chemical group 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 8
- 230000003115 biocidal effect Effects 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 8
- 238000011161 development Methods 0.000 description 8
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 description 8
- 125000003302 alkenyloxy group Chemical group 0.000 description 7
- 125000005133 alkynyloxy group Chemical group 0.000 description 7
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 7
- 150000003857 carboxamides Chemical class 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 125000004995 haloalkylthio group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 7
- 244000052769 pathogen Species 0.000 description 7
- 150000003904 phospholipids Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 150000003871 sulfonates Chemical class 0.000 description 7
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 101150065749 Churc1 gene Proteins 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 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
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 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
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- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| US34660610P | 2010-05-20 | 2010-05-20 | |
| US61/346,606 | 2010-05-20 | ||
| PCT/US2011/032599 WO2011146182A1 (en) | 2010-05-20 | 2011-04-15 | Fungicidal oximes and hydrazones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011256730A1 AU2011256730A1 (en) | 2013-07-11 |
| AU2011256730B2 true AU2011256730B2 (en) | 2015-07-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011256730A Ceased AU2011256730B2 (en) | 2010-05-20 | 2011-04-15 | Fungicidal oximes and hydrazones |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8722678B2 (enExample) |
| EP (1) | EP2571866A1 (enExample) |
| JP (1) | JP5769799B2 (enExample) |
| KR (1) | KR20130109975A (enExample) |
| CN (1) | CN102933577B (enExample) |
| AR (1) | AR082373A1 (enExample) |
| AU (1) | AU2011256730B2 (enExample) |
| BR (1) | BR112012026708A2 (enExample) |
| IL (1) | IL222549A0 (enExample) |
| MX (1) | MX2012013315A (enExample) |
| TW (1) | TWI501964B (enExample) |
| WO (1) | WO2011146182A1 (enExample) |
| ZA (1) | ZA201207373B (enExample) |
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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 |
| BR112012027762B1 (pt) * | 2010-04-28 | 2018-06-05 | Bayer Intellectual Property Gmbh | Derivados de cetoheteroarilpiperidina e - piperazina como fungicidas |
| EP2921481A1 (de) | 2011-12-27 | 2015-09-23 | Bayer Intellectual Property GmbH | 4-piperidine carboxylic acid derivatives |
| KR101800607B1 (ko) | 2012-02-02 | 2017-11-23 | 액테리온 파마슈티칼 리미티드 | ４-(벤조이미다졸-２-일)-티아졸 화합물 및 관련 아자 유도체 |
| WO2014154530A1 (en) * | 2013-03-25 | 2014-10-02 | Syngenta Participations Ag | Microbiocidal pyrazole derivatives |
| EP2801575A1 (en) | 2013-05-07 | 2014-11-12 | Bayer CropScience AG | Heteroaryldihydropyridine derivatives as fungicides |
| US9717243B2 (en) | 2013-06-24 | 2017-08-01 | Bayer Cropscience Aktiengesellschaft | Piperidinecarboxylic acid derivatives as fungicides |
| JP6330040B2 (ja) | 2013-07-22 | 2018-05-23 | 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 | １−（ピペラジン−１−イル）−２−（［１，２，４］トリアゾール−１−イル）−エタノン誘導体 |
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| ES2753582T3 (es) | 2014-06-11 | 2020-04-13 | Bayer Cropscience Ag | Preparación de piperidin-4-carbotioamida |
| 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 |
| CN104650064B (zh) * | 2014-12-17 | 2017-12-05 | 南开大学 | 一类氨基噻唑羧酸衍生物及其制备方法和用途 |
| CN104650059B (zh) * | 2014-12-17 | 2018-06-22 | 南开大学 | 一类噻唑酮肟醚类衍生物及其制备方法和用途 |
| PT3245203T (pt) | 2015-01-15 | 2019-02-08 | Idorsia Pharmaceuticals Ltd | Derivados de hidroxialquil-piperazina como modeladores do recetor cxcr3 |
| AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
| WO2016139165A1 (en) | 2015-03-05 | 2016-09-09 | Bayer Cropscience Aktiengesellschaft | Process for preparing piperidine-4-carbothioamide hydrochloride |
| JP6371915B2 (ja) * | 2015-09-18 | 2018-08-08 | 株式会社エス・ディー・エス バイオテック | ４−（４−ホルミルチアゾリル）ピペリジン化合物の製造方法 |
| CN106916084B (zh) | 2015-12-25 | 2019-06-11 | 沈阳中化农药化工研发有限公司 | 一种丙二腈肟醚类化合物及其用途 |
| CN114702411A (zh) | 2016-02-08 | 2022-07-05 | 高文作物保护公司 | 1,2-苯二甲醇化合物的制造方法 |
| AU2016392652B2 (en) | 2016-02-08 | 2021-01-21 | Gowan Company, L.L.C. | Fungicidal Composition |
| US12053540B2 (en) | 2018-12-04 | 2024-08-06 | Virox Technologies Inc. | Antimicrobial compositions containing solvents including a C3-C5 N-alkyl-gamma-butyrolactam |
| BR112021006553A2 (pt) | 2018-12-04 | 2021-07-13 | Virox Technologies Inc. | composições antimicrobianas contendo c3-c5 n-alquil-gama-butirolactama e usos dos mesmos |
| US12052990B2 (en) | 2018-12-04 | 2024-08-06 | Virox Technologies Inc. | C3-C5 n-alkyl-gamma-butyrolactam containing antimicrobial compositions and methods of using same |
| CN115304536B (zh) * | 2022-07-26 | 2023-09-22 | 合肥工业大学 | 一种吲哚啉-2-酮化合物衍生物的制备及用途 |
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- 2011-04-15 WO PCT/US2011/032599 patent/WO2011146182A1/en not_active Ceased
- 2011-04-15 BR BR112012026708A patent/BR112012026708A2/pt not_active Application Discontinuation
- 2011-04-15 JP JP2013511164A patent/JP5769799B2/ja not_active Expired - Fee Related
- 2011-04-15 MX MX2012013315A patent/MX2012013315A/es active IP Right Grant
- 2011-04-15 AU AU2011256730A patent/AU2011256730B2/en not_active Ceased
- 2011-04-15 EP EP11717108A patent/EP2571866A1/en not_active Withdrawn
- 2011-04-15 US US13/640,092 patent/US8722678B2/en not_active Expired - Fee Related
- 2011-04-15 CN CN201180025065.6A patent/CN102933577B/zh not_active Expired - Fee Related
- 2011-05-04 TW TW100115643A patent/TWI501964B/zh not_active IP Right Cessation
- 2011-05-20 AR ARP110101745A patent/AR082373A1/es unknown
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| WO2007014290A2 (en) * | 2005-07-26 | 2007-02-01 | E. I. Du Pont De Nemours And Company | Fungicidal carboxamides |
| WO2008013925A2 (en) * | 2006-07-27 | 2008-01-31 | 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 |
| WO2008091594A2 (en) * | 2007-01-24 | 2008-07-31 | E. I. Du Pont De Nemours And Company | Fungicidal mixtures |
| WO2009055514A2 (en) * | 2007-10-23 | 2009-04-30 | E. I. Du Pont De Nemours And Company | Fungicidal mixtures |
| WO2009094445A2 (en) * | 2008-01-25 | 2009-07-30 | E. I. Du Pont De Nemours And Company | Fungicidal hetercyclic compounds |
| WO2009094407A2 (en) * | 2008-01-25 | 2009-07-30 | E. I. Du Pont De Nemours And Company | Fungicidal amides |
| WO2010066353A1 (de) * | 2008-12-11 | 2010-06-17 | Bayer Cropscience Ag | Thiazolyoximether und -hydrazone asl pflanzenschutzmittel |
| WO2011134969A1 (de) * | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Ketoheteroarylpiperidin und -piperazin derivate als fungizide |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2012013315A (es) | 2012-12-05 |
| JP5769799B2 (ja) | 2015-08-26 |
| US20130030002A1 (en) | 2013-01-31 |
| WO2011146182A1 (en) | 2011-11-24 |
| TWI501964B (zh) | 2015-10-01 |
| TW201144305A (en) | 2011-12-16 |
| ZA201207373B (en) | 2014-12-23 |
| US8722678B2 (en) | 2014-05-13 |
| CN102933577A (zh) | 2013-02-13 |
| JP2013528602A (ja) | 2013-07-11 |
| EP2571866A1 (en) | 2013-03-27 |
| CN102933577B (zh) | 2014-08-06 |
| IL222549A0 (en) | 2012-12-31 |
| KR20130109975A (ko) | 2013-10-08 |
| AR082373A1 (es) | 2012-12-05 |
| AU2011256730A1 (en) | 2013-07-11 |
| BR112012026708A2 (pt) | 2015-09-22 |
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