AU2011256730B2 - Fungicidal oximes and hydrazones - Google Patents

Info

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

2010-05-20

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

Links

• Espacenet
• Global Dossier
• Discuss

• 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
• 230000018109 developmental process Effects 0.000 description 8
• 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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