CA1203539A - N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides - Google Patents
N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicidesInfo
- Publication number
- CA1203539A CA1203539A CA000359647A CA359647A CA1203539A CA 1203539 A CA1203539 A CA 1203539A CA 000359647 A CA000359647 A CA 000359647A CA 359647 A CA359647 A CA 359647A CA 1203539 A CA1203539 A CA 1203539A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- amino
- acetyl
- oxazolidin
- 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
- 239000000417 fungicide Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 25
- -1 phenyl-acetyl Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims abstract description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 7
- 208000024386 fungal infectious disease Diseases 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 239000002689 soil Substances 0.000 claims abstract description 7
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 17
- 230000000855 fungicidal effect Effects 0.000 description 14
- 208000015181 infectious disease Diseases 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 231100000674 Phytotoxicity Toxicity 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910001868 water Inorganic materials 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 241001223281 Peronospora Species 0.000 description 5
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- 230000001143 conditioned effect Effects 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CCHJMGDYNLOYKM-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NN CCHJMGDYNLOYKM-UHFFFAOYSA-N 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 241000582441 Peronospora tabacina Species 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- ZLCKDYMZBZNBMJ-UHFFFAOYSA-N 2-bromoethyl carbonochloridate Chemical compound ClC(=O)OCCBr ZLCKDYMZBZNBMJ-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- UOAVOZAOARIKEL-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidine-2,4-dione Chemical class O=C1COC(=O)N1C1=CC=CC=C1 UOAVOZAOARIKEL-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical class C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000432137A CA1296340C (en) | 1979-09-07 | 1983-07-08 | N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25538/79A IT1123564B (it) | 1979-09-07 | 1979-09-07 | N-aril-n-acil-3-ammino-ossazolidin-2-oni fungicidi |
| IT25538A/79 | 1979-09-07 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000432137A Division CA1296340C (en) | 1979-09-07 | 1983-07-08 | N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1203539A true CA1203539A (en) | 1986-04-22 |
Family
ID=11217010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359647A Expired CA1203539A (en) | 1979-09-07 | 1980-09-05 | N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5655381A (en, 2012) |
| AR (1) | AR228138A1 (en, 2012) |
| AU (1) | AU545683B2 (en, 2012) |
| BE (1) | BE885117A (en, 2012) |
| BR (1) | BR8005645A (en, 2012) |
| CA (1) | CA1203539A (en, 2012) |
| CH (1) | CH645513A5 (en, 2012) |
| CY (1) | CY1235A (en, 2012) |
| DE (1) | DE3033161A1 (en, 2012) |
| ES (1) | ES8106713A1 (en, 2012) |
| FR (1) | FR2464649A1 (en, 2012) |
| GB (1) | GB2058071B (en, 2012) |
| GR (1) | GR69955B (en, 2012) |
| IL (1) | IL60950A (en, 2012) |
| IT (1) | IT1123564B (en, 2012) |
| KE (1) | KE3383A (en, 2012) |
| NL (1) | NL8004962A (en, 2012) |
| OA (1) | OA06743A (en, 2012) |
| ZA (1) | ZA805450B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
| DE3231605A1 (de) * | 1981-02-05 | 1983-02-10 | Sandoz Ag | Fungizide |
| WO1982002714A1 (en) * | 1981-02-09 | 1982-08-19 | Sandmeier Rudolf | Fungicides |
| NL8203049A (nl) * | 1981-08-04 | 1983-03-01 | Montedison Spa | Oxazolinonverbinding met fungicidewerking en werkwijzen voor het bereiden en toepassen van deze verbinding. |
| IT1168031B (it) * | 1981-10-01 | 1987-05-20 | Montedison Spa | Composti fungicidi |
| CH654979A5 (de) * | 1982-01-26 | 1986-03-27 | Sandoz Ag | Fungizide und ihre verwendung. |
| IT1152196B (it) * | 1982-05-27 | 1986-12-31 | Montedison Spa | Composto fungicida |
| GB8504181D0 (en) * | 1985-02-19 | 1985-03-20 | Sandoz Ltd | Fungicides |
| US4771063A (en) * | 1985-06-06 | 1988-09-13 | Montedison S.P.A | Fungicidally active N-(2-methyl-5-chlorophenyl)-N-methoxyacetyl-3-amino-1,3-oxazolidin-2-one |
| EP0284555A1 (de) * | 1987-03-12 | 1988-09-28 | Ciba-Geigy Ag | Verfahren zur Herstellung von N-Acyl-N-(oxazolidin-2-on-3-yl)-2,6-dialkyl-3-chloranilinen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097262A (en) * | 1977-04-22 | 1978-06-27 | E. I. Du Pont De Nemours And Company | Herbicidal acetamides |
| CH646158A5 (en) * | 1979-08-16 | 1984-11-15 | Sandoz Ag | Fungicides |
| BE884661A (fr) * | 1979-08-16 | 1981-02-09 | Sandoz Sa | Nouvelles 3-amino-oxazolidine-2-ones, leur preparation et leur utilisation comme agents fongicides |
| EP0030923A1 (de) * | 1979-12-18 | 1981-06-24 | Ciba-Geigy Ag | 3-(N-Acyl-phenylamino)-oxazolidin-2-one, Verfahren zu ihrer Herstellung sowie deren Verwendung als Mikrobizide oder in mikrobiziden Mitteln |
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
-
1979
- 1979-09-07 IT IT25538/79A patent/IT1123564B/it active
-
1980
- 1980-09-01 NL NL8004962A patent/NL8004962A/nl not_active Application Discontinuation
- 1980-09-02 FR FR8018915A patent/FR2464649A1/fr active Granted
- 1980-09-02 IL IL60950A patent/IL60950A/xx unknown
- 1980-09-02 AU AU61949/80A patent/AU545683B2/en not_active Ceased
- 1980-09-02 CH CH660380A patent/CH645513A5/it not_active IP Right Cessation
- 1980-09-03 JP JP12124080A patent/JPS5655381A/ja active Granted
- 1980-09-03 ZA ZA00805450A patent/ZA805450B/xx unknown
- 1980-09-03 DE DE19803033161 patent/DE3033161A1/de not_active Ceased
- 1980-09-04 BR BR8005645A patent/BR8005645A/pt not_active IP Right Cessation
- 1980-09-05 GR GR62813A patent/GR69955B/el unknown
- 1980-09-05 BE BE0/202012A patent/BE885117A/fr not_active IP Right Cessation
- 1980-09-05 CA CA000359647A patent/CA1203539A/en not_active Expired
- 1980-09-06 ES ES494856A patent/ES8106713A1/es not_active Expired
- 1980-09-08 GB GB8028922A patent/GB2058071B/en not_active Expired
- 1980-09-08 AR AR282439A patent/AR228138A1/es active
- 1980-09-08 CY CY1235A patent/CY1235A/en unknown
-
1981
- 1981-02-13 OA OA57326A patent/OA06743A/xx unknown
-
1984
- 1984-03-01 KE KE3383A patent/KE3383A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR8005645A (pt) | 1981-03-17 |
| IT7925538A0 (it) | 1979-09-07 |
| NL8004962A (nl) | 1981-03-10 |
| GB2058071B (en) | 1983-11-09 |
| AR228138A1 (es) | 1983-01-31 |
| JPH0240664B2 (en, 2012) | 1990-09-12 |
| GR69955B (en, 2012) | 1982-07-22 |
| JPS5655381A (en) | 1981-05-15 |
| CY1235A (en) | 1984-06-29 |
| DE3033161A1 (de) | 1981-04-02 |
| FR2464649A1 (fr) | 1981-03-20 |
| GB2058071A (en) | 1981-04-08 |
| ZA805450B (en) | 1981-08-26 |
| CH645513A5 (it) | 1984-10-15 |
| OA06743A (fr) | 1982-06-30 |
| KE3383A (en) | 1984-03-23 |
| ES494856A0 (es) | 1981-09-01 |
| IL60950A (en) | 1985-05-31 |
| BE885117A (fr) | 1981-03-05 |
| FR2464649B1 (en, 2012) | 1983-07-08 |
| IT1123564B (it) | 1986-04-30 |
| ES8106713A1 (es) | 1981-09-01 |
| AU6194980A (en) | 1981-03-12 |
| AU545683B2 (en) | 1985-07-25 |
| IL60950A0 (en) | 1980-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2793956B2 (ja) | トリアジン誘導体およびそれを有効成分とする除草剤 | |
| US4229465A (en) | Cyanopyrrole derivatives | |
| DE69410894T2 (de) | 2-Aminothiazolcarboxamid Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von phytopathogenen Organismen | |
| CS196415B2 (en) | Fungicide and process for preparing effective compounds | |
| CA1203539A (en) | N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides | |
| JPS626548B2 (en, 2012) | ||
| CS201517B2 (en) | Fungicide means | |
| CS241520B2 (en) | Fungicide and/or nematocide and method of active substance preparation | |
| US4152460A (en) | 3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines | |
| CA1296340C (en) | N-aryl-n-acyl-3-amino-oxazolidin-2-ones fungicides | |
| US4771063A (en) | Fungicidally active N-(2-methyl-5-chlorophenyl)-N-methoxyacetyl-3-amino-1,3-oxazolidin-2-one | |
| US4303667A (en) | Phenylprrole derivatives | |
| US4187096A (en) | Biocidally-active 1,3-benzodithiole-2-thione compounds | |
| US4038403A (en) | Benzotriazole ovicides and larvicides | |
| US4331669A (en) | Fungicidal pyridyl arylureas, compositions containing them and method of controlling fungi and bacteria | |
| JPH05125057A (ja) | １−フエニル−４−トリフルオロメチルウラシル誘導体およびそれを有効成分とする除草剤 | |
| JPH027949B2 (en, 2012) | ||
| US4240821A (en) | Biocidally-active 1,3-benzodithiole-2-thione compounds | |
| EP0121344A2 (en) | N,N-substituted azolecarboxamide derivatives useful as fungicides and nematicides | |
| US5721192A (en) | Aminosulfonyl ureas | |
| US4472583A (en) | 4-Isothiocyanato-2,6-bis-(trifluoromethyl)pyridine | |
| US4920142A (en) | Fungicidal imidazole derivatives | |
| US4357346A (en) | N-Haloalkyl thiobenzanilides and their use as fungicides | |
| US4249932A (en) | 5-Phenoxymethyl substituted oxazolidine herbicide antidotes | |
| KR0160329B1 (ko) | N-벤조일 카바메이트 유도체와 이의 제조방법 및 이를 함유하는 농약조성물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |