CA1082185A - Substituted isoxazolines for control of plant phytopathogens - Google Patents
Substituted isoxazolines for control of plant phytopathogensInfo
- Publication number
- CA1082185A CA1082185A CA277,139A CA277139A CA1082185A CA 1082185 A CA1082185 A CA 1082185A CA 277139 A CA277139 A CA 277139A CA 1082185 A CA1082185 A CA 1082185A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- ncs
- isoxazoline
- alkyl
- 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.)
- Expired
Links
- 150000002547 isoxazolines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 230000002538 fungal effect Effects 0.000 claims abstract description 8
- 241000196324 Embryophyta Species 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 34
- -1 isoxazoline compound Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 230000002411 adverse Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- WXSCAAADPSCIEQ-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-pyridin-2-yl-4,5-dihydro-1,2-oxazole Chemical compound O1C(CN=C=S)CC(C=2N=CC=CC=2)=N1 WXSCAAADPSCIEQ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- CVPSVRRTBCYIMK-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-(isothiocyanatomethyl)-4,5-dihydro-1,2-oxazole Chemical compound ClC1=CC=CC(Cl)=C1C1=NOC(CN=C=S)C1 CVPSVRRTBCYIMK-UHFFFAOYSA-N 0.000 claims description 3
- VXKQBEGLIRWDPK-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(isothiocyanatomethyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(Cl)=CC=C1C1=NOC(CN=C=S)C1 VXKQBEGLIRWDPK-UHFFFAOYSA-N 0.000 claims description 3
- VWKLMYQGAUNDDI-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(C)=CC=C1C1=NOC(CN=C=S)C1 VWKLMYQGAUNDDI-UHFFFAOYSA-N 0.000 claims description 3
- RUQRQEFSCXRXKR-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NOC(CN=C=S)C1 RUQRQEFSCXRXKR-UHFFFAOYSA-N 0.000 claims description 3
- 241000219094 Vitaceae Species 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 235000021021 grapes Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 7
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- 125000003118 aryl group Chemical group 0.000 abstract description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 10
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- 241001465180 Botrytis Species 0.000 description 5
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- 235000012333 Vitis X labruscana Nutrition 0.000 description 5
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000070406 Malus silvestris Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 235000021307 Triticum Nutrition 0.000 description 3
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- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- LUVOYHINQVUVDI-UHFFFAOYSA-N (3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methanamine Chemical compound O1C(CN)CC(C=2C=CC=CC=2)=N1 LUVOYHINQVUVDI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
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- PJWAJMSEWZQRRY-UHFFFAOYSA-N 3-(4-bromophenyl)-5-(isothiocyanatomethyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(Br)=CC=C1C1=NOC(CN=C=S)C1 PJWAJMSEWZQRRY-UHFFFAOYSA-N 0.000 description 1
- JIBKUJKWYKAKMX-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-(isothiocyanatomethyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(F)=CC=C1C1=NOC(CN=C=S)C1 JIBKUJKWYKAKMX-UHFFFAOYSA-N 0.000 description 1
- XYFVPKIYTWHWFP-UHFFFAOYSA-N 3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(C)=CC=C1C1=NOCC1 XYFVPKIYTWHWFP-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- MMBUQZYTJHVQCS-UHFFFAOYSA-N 3-isothiocyanato-4,5-dihydro-1,2-oxazole Chemical compound S=C=NC1=NOCC1 MMBUQZYTJHVQCS-UHFFFAOYSA-N 0.000 description 1
- MFGFCOGBOWRZRS-UHFFFAOYSA-N 3-methyl-4-phenyl-4,5-dihydro-1,2-oxazole Chemical compound CC1=NOCC1C1=CC=CC=C1 MFGFCOGBOWRZRS-UHFFFAOYSA-N 0.000 description 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 1
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- ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 1
- OPIJVFIBEWIDRT-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-(2-propan-2-ylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound CC(C)C1=CC=CC=C1C1=NOC(CN=C=S)C1 OPIJVFIBEWIDRT-UHFFFAOYSA-N 0.000 description 1
- FMTFSSWZSHETLN-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC(OC)=CC=C1C1=NOC(CN=C=S)C1 FMTFSSWZSHETLN-UHFFFAOYSA-N 0.000 description 1
- SBMWQOHGBQECHG-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-(4-nitrophenyl)-4,5-dihydro-1,2-oxazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC(CN=C=S)C1 SBMWQOHGBQECHG-UHFFFAOYSA-N 0.000 description 1
- CTIGEQVWZNPRFZ-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-(4-phenylphenyl)-4,5-dihydro-1,2-oxazole Chemical compound O1C(CN=C=S)CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 CTIGEQVWZNPRFZ-UHFFFAOYSA-N 0.000 description 1
- XQQWMKULGRWVNS-UHFFFAOYSA-N 5-(isothiocyanatomethyl)-3-phenyl-4,5-dihydro-1,2-oxazole Chemical compound O1C(CN=C=S)CC(C=2C=CC=CC=2)=N1 XQQWMKULGRWVNS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000607534 Aeromonas Species 0.000 description 1
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000209437 Cabomba Species 0.000 description 1
- 241000209439 Cabomba caroliniana Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000222235 Colletotrichum orbiculare Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241000202938 Mycoplasma hyorhinis Species 0.000 description 1
- KMHBMCMMRGAQMS-UHFFFAOYSA-N N-[2-[3-(2-hydroxy-5-nitrophenyl)-4,5-dihydro-1,2-oxazol-5-yl]ethyl]-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide Chemical compound N=1N=C(C)SC=1N(C(=O)C)CCC(ON=1)CC=1C1=CC([N+]([O-])=O)=CC=C1O KMHBMCMMRGAQMS-UHFFFAOYSA-N 0.000 description 1
- KIAHBFVFCPFRHO-UHFFFAOYSA-N NCC1CC(=NO1)C1=CC2=CC=CC=C2C=C1.C(#N)CCC1CC(=NO1)C1=CC=CC2=CC=CC=C12 Chemical compound NCC1CC(=NO1)C1=CC2=CC=CC=C2C=C1.C(#N)CCC1CC(=NO1)C1=CC=CC2=CC=CC=C12 KIAHBFVFCPFRHO-UHFFFAOYSA-N 0.000 description 1
- 241000721619 Najas Species 0.000 description 1
- 241000555917 Najas marina Species 0.000 description 1
- 241000905012 Neonectria candida Species 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 241000589774 Pseudomonas sp. Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241001533580 Septoria lycopersici Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241001080482 Urbanus proteus Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229940008015 lithium carbonate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- HOKWACLNOVXXRU-UHFFFAOYSA-N methyl n-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]carbamate Chemical compound O1C(CNC(=O)OC)CC(C=2C=CC=CC=2)=N1 HOKWACLNOVXXRU-UHFFFAOYSA-N 0.000 description 1
- RGVMJBAUCBSEGO-UHFFFAOYSA-N methyl n-prop-2-enylcarbamate Chemical compound COC(=O)NCC=C RGVMJBAUCBSEGO-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- UIIZGAXKZZRCBN-UHFFFAOYSA-N n-[(4-bromophenyl)methylidene]hydroxylamine Chemical compound ON=CC1=CC=C(Br)C=C1 UIIZGAXKZZRCBN-UHFFFAOYSA-N 0.000 description 1
- KWJIGKIXKAIUBR-UHFFFAOYSA-N n-[[3-(4-chlorophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]-n-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide Chemical compound N=1N=C(C)SC=1N(C(=O)C)CC(ON=1)CC=1C1=CC=C(Cl)C=C1 KWJIGKIXKAIUBR-UHFFFAOYSA-N 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69566876A | 1976-06-14 | 1976-06-14 | |
| US695,668 | 1976-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082185A true CA1082185A (en) | 1980-07-22 |
Family
ID=24793992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,139A Expired CA1082185A (en) | 1976-06-14 | 1977-04-27 | Substituted isoxazolines for control of plant phytopathogens |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS52153959A (cs) |
| BE (1) | BE855602A (cs) |
| BR (2) | BR7703803A (cs) |
| CA (1) | CA1082185A (cs) |
| CH (1) | CH627049A5 (cs) |
| DE (1) | DE2725763A1 (cs) |
| FR (1) | FR2355010A1 (cs) |
| GB (1) | GB1581583A (cs) |
| IE (1) | IE44819B1 (cs) |
| IL (1) | IL51948A (cs) |
| IT (1) | IT1115337B (cs) |
| NL (1) | NL7706558A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10703732B2 (en) * | 2015-02-27 | 2020-07-07 | Op Bio Factory Co., Ltd. | Method for producing kakeromycin and derivatives thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU757197B2 (en) * | 1998-02-13 | 2003-02-06 | Pharmacia & Upjohn Company | Substituted aminophenyl isoxazoline derivatives useful as antimicrobials |
-
1977
- 1977-04-14 IE IE778/77A patent/IE44819B1/en unknown
- 1977-04-26 IL IL51948A patent/IL51948A/xx unknown
- 1977-04-27 CA CA277,139A patent/CA1082185A/en not_active Expired
- 1977-05-27 IT IT24104/77A patent/IT1115337B/it active
- 1977-06-07 DE DE19772725763 patent/DE2725763A1/de not_active Withdrawn
- 1977-06-09 GB GB24189/77A patent/GB1581583A/en not_active Expired
- 1977-06-10 BE BE1008185A patent/BE855602A/xx unknown
- 1977-06-13 BR BR7703803A patent/BR7703803A/pt unknown
- 1977-06-13 JP JP7043277A patent/JPS52153959A/ja active Pending
- 1977-06-13 FR FR7718050A patent/FR2355010A1/fr active Granted
- 1977-06-14 NL NL7706558A patent/NL7706558A/xx not_active Application Discontinuation
- 1977-06-14 CH CH730777A patent/CH627049A5/de not_active IP Right Cessation
- 1977-06-14 BR BR7703863A patent/BR7703863A/pt unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10703732B2 (en) * | 2015-02-27 | 2020-07-07 | Op Bio Factory Co., Ltd. | Method for producing kakeromycin and derivatives thereof |
| US11753385B2 (en) | 2015-02-27 | 2023-09-12 | Op Bio Factory Co., Ltd. | Method for producing kakeromycin and derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7706558A (nl) | 1977-12-16 |
| JPS52153959A (en) | 1977-12-21 |
| IT1115337B (it) | 1986-02-03 |
| BE855602A (fr) | 1977-12-12 |
| GB1581583A (en) | 1980-12-17 |
| IE44819B1 (en) | 1982-04-07 |
| IL51948A (en) | 1980-06-30 |
| FR2355010B1 (cs) | 1980-02-01 |
| BR7703803A (pt) | 1978-04-18 |
| CH627049A5 (en) | 1981-12-31 |
| FR2355010A1 (fr) | 1978-01-13 |
| BR7703863A (pt) | 1978-04-25 |
| IE44819L (en) | 1977-12-14 |
| DE2725763A1 (de) | 1977-12-22 |
| IL51948A0 (en) | 1977-06-30 |
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