PL126290B1 - Method of manufacture of novel oxazolydinylacetamides and fungicide - Google Patents
Method of manufacture of novel oxazolydinylacetamides and fungicide Download PDFInfo
- Publication number
- PL126290B1 PL126290B1 PL1980226259A PL22625980A PL126290B1 PL 126290 B1 PL126290 B1 PL 126290B1 PL 1980226259 A PL1980226259 A PL 1980226259A PL 22625980 A PL22625980 A PL 22625980A PL 126290 B1 PL126290 B1 PL 126290B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- carbon atoms
- model
- furyl
- pattern
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 14
- 239000000417 fungicide Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- FKAWHEVTKRDZCI-UHFFFAOYSA-N N-(1,3-oxazolidin-2-yl)acetamide Chemical class C(C)(=O)NC1OCCN1 FKAWHEVTKRDZCI-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241000233866 Fungi Species 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 241001281803 Plasmopara viticola Species 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000025221 Humulus lupulus Species 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000233654 Oomycetes Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000918585 Pythium aphanidermatum Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 240000003829 Sorghum propinquum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- CCHJMGDYNLOYKM-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NN CCHJMGDYNLOYKM-UHFFFAOYSA-N 0.000 description 1
- GQKQMDUOOZVZFD-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine;hydron;chloride Chemical compound [Cl-].CC1=CC=CC(C)=C1N[NH3+] GQKQMDUOOZVZFD-UHFFFAOYSA-N 0.000 description 1
- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
- DABGYYJVDOKEEV-UHFFFAOYSA-N 2-chloroethyl n-(2,6-dimethylanilino)carbamate Chemical compound CC1=CC=CC(C)=C1NNC(=O)OCCCl DABGYYJVDOKEEV-UHFFFAOYSA-N 0.000 description 1
- AAUZVQSFZKPZGG-UHFFFAOYSA-N 2-chloroethyl n-(n-(2-methoxyacetyl)-2,6-dimethylanilino)carbamate Chemical compound ClCCOC(=O)NN(C(=O)COC)C1=C(C)C=CC=C1C AAUZVQSFZKPZGG-UHFFFAOYSA-N 0.000 description 1
- 241000233684 Bremia Species 0.000 description 1
- 241000233685 Bremia lactucae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 241000596141 Peronosclerospora sorghi Species 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000582441 Peronospora tabacina Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 241000342317 Sclerospora Species 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7928603 | 1979-08-16 | ||
| GB8013720 | 1980-04-25 | ||
| GB8013719 | 1980-04-25 | ||
| GB8013721 | 1980-04-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL226259A1 PL226259A1 (it) | 1981-04-24 |
| PL126290B1 true PL126290B1 (en) | 1983-07-30 |
Family
ID=27449134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980226259A PL126290B1 (en) | 1979-08-16 | 1980-08-15 | Method of manufacture of novel oxazolydinylacetamides and fungicide |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT380014B (it) |
| AU (1) | AU534946B2 (it) |
| BR (1) | BR8005179A (it) |
| CA (1) | CA1303046C (it) |
| CH (1) | CH646158A5 (it) |
| DK (1) | DK151960C (it) |
| DZ (1) | DZ248A1 (it) |
| FR (1) | FR2463132A1 (it) |
| HU (1) | HU186740B (it) |
| IE (1) | IE50501B1 (it) |
| IL (1) | IL60837A (it) |
| IT (1) | IT1194679B (it) |
| KE (1) | KE3439A (it) |
| NL (1) | NL188751C (it) |
| PL (1) | PL126290B1 (it) |
| YU (1) | YU42530B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1123564B (it) * | 1979-09-07 | 1986-04-30 | Montedison Spa | N-aril-n-acil-3-ammino-ossazolidin-2-oni fungicidi |
| IT1152196B (it) * | 1982-05-27 | 1986-12-31 | Montedison Spa | Composto fungicida |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH633942A5 (en) * | 1977-02-04 | 1983-01-14 | Ciba Geigy Ag | Microbicidal composition, process for the preparation of the active substance, and its use for controlling phytopathogenic fungi |
-
1980
- 1980-08-08 CH CH603580A patent/CH646158A5/de not_active IP Right Cessation
- 1980-08-10 DZ DZ805942A patent/DZ248A1/fr active
- 1980-08-13 YU YU2040/80A patent/YU42530B/xx unknown
- 1980-08-13 NL NLAANVRAGE8004584,A patent/NL188751C/xx not_active IP Right Cessation
- 1980-08-14 IL IL60837A patent/IL60837A/xx unknown
- 1980-08-14 IT IT24168/80A patent/IT1194679B/it active
- 1980-08-14 IE IE1723/80A patent/IE50501B1/en not_active IP Right Cessation
- 1980-08-14 AT AT0416080A patent/AT380014B/de not_active IP Right Cessation
- 1980-08-14 AU AU61462/80A patent/AU534946B2/en not_active Expired
- 1980-08-14 CA CA000358259A patent/CA1303046C/en not_active Expired - Lifetime
- 1980-08-15 PL PL1980226259A patent/PL126290B1/pl unknown
- 1980-08-15 BR BR8005179A patent/BR8005179A/pt not_active IP Right Cessation
- 1980-08-15 HU HU802045A patent/HU186740B/hu unknown
- 1980-08-15 DK DK355280A patent/DK151960C/da not_active IP Right Cessation
- 1980-08-18 FR FR8018043A patent/FR2463132A1/fr active Granted
-
1984
- 1984-08-13 KE KE3439A patent/KE3439A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8024168A0 (it) | 1980-08-14 |
| CH646158A5 (en) | 1984-11-15 |
| DZ248A1 (fr) | 2004-09-13 |
| HU186740B (en) | 1985-09-30 |
| PL226259A1 (it) | 1981-04-24 |
| IT8024168A1 (it) | 1982-02-14 |
| ATA416080A (de) | 1985-08-15 |
| IE801723L (en) | 1981-02-16 |
| DK151960C (da) | 1988-07-11 |
| AU534946B2 (en) | 1984-02-23 |
| YU204080A (en) | 1983-02-28 |
| DK151960B (da) | 1988-01-18 |
| DK355280A (da) | 1981-02-17 |
| IE50501B1 (en) | 1986-04-30 |
| NL188751B (nl) | 1992-04-16 |
| CA1303046C (en) | 1992-06-09 |
| NL188751C (nl) | 1992-09-16 |
| BR8005179A (pt) | 1981-03-04 |
| KE3439A (en) | 1984-08-24 |
| IT1194679B (it) | 1988-09-22 |
| NL8004584A (nl) | 1981-02-18 |
| IL60837A (en) | 1984-02-29 |
| AU6146280A (en) | 1981-02-19 |
| FR2463132B1 (it) | 1983-11-18 |
| FR2463132A1 (fr) | 1981-02-20 |
| AT380014B (de) | 1986-03-25 |
| YU42530B (en) | 1988-10-31 |
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