DE3033161A1 - N-aryl-n-acyl-3-amino-oxazolidin-2-one und diese enthaltende fungizide - Google Patents
N-aryl-n-acyl-3-amino-oxazolidin-2-one und diese enthaltende fungizideInfo
- Publication number
- DE3033161A1 DE3033161A1 DE19803033161 DE3033161A DE3033161A1 DE 3033161 A1 DE3033161 A1 DE 3033161A1 DE 19803033161 DE19803033161 DE 19803033161 DE 3033161 A DE3033161 A DE 3033161A DE 3033161 A1 DE3033161 A1 DE 3033161A1
- Authority
- DE
- Germany
- Prior art keywords
- oxazolidin
- amino
- dimethylphenyl
- alkyl
- phenyl
- 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.)
- Ceased
Links
- 239000000417 fungicide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 2,6-dimethylphenyl Chemical group 0.000 claims description 17
- 230000000855 fungicidal effect Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
- 244000061176 Nicotiana tabacum Species 0.000 claims description 3
- KYCJNIUHWNJNCT-UHFFFAOYSA-N 3-Amino-2-oxazolidone Chemical compound NN1CCOC1=O KYCJNIUHWNJNCT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241001281803 Plasmopara viticola Species 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 229960000649 oxyphenbutazone Drugs 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 241000582441 Peronospora tabacina Species 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- 208000015181 infectious disease Diseases 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 231100000674 Phytotoxicity Toxicity 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 150000001266 acyl halides Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 241001223281 Peronospora Species 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000000034 method 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
- 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 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CCHJMGDYNLOYKM-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NN CCHJMGDYNLOYKM-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009472 formulation 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- 239000004471 Glycine Substances 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
- 206010034972 Photosensitivity reaction Diseases 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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003570 air Substances 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
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3033161A1 true DE3033161A1 (de) | 1981-04-02 |
Family
ID=11217010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803033161 Ceased DE3033161A1 (de) | 1979-09-07 | 1980-09-03 | N-aryl-n-acyl-3-amino-oxazolidin-2-one und diese enthaltende fungizide |
Country Status (19)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3231605A1 (de) * | 1981-02-05 | 1983-02-10 | Sandoz Ag | Fungizide |
| DE3231606A1 (de) * | 1981-02-09 | 1983-02-10 | Sandoz Ag | Fungizide |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
Family Cites Families (4)
| 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 |
| BE884661A (fr) * | 1979-08-16 | 1981-02-09 | Sandoz Sa | Nouvelles 3-amino-oxazolidine-2-ones, leur preparation et leur utilisation comme agents fongicides |
| CH646158A5 (en) * | 1979-08-16 | 1984-11-15 | Sandoz Ag | Fungicides |
| 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 |
-
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 IL IL60950A patent/IL60950A/xx unknown
- 1980-09-02 CH CH660380A patent/CH645513A5/it not_active IP Right Cessation
- 1980-09-02 FR FR8018915A patent/FR2464649A1/fr active Granted
- 1980-09-02 AU AU61949/80A patent/AU545683B2/en not_active Ceased
- 1980-09-03 DE DE19803033161 patent/DE3033161A1/de not_active Ceased
- 1980-09-03 JP JP12124080A patent/JPS5655381A/ja active Granted
- 1980-09-03 ZA ZA00805450A patent/ZA805450B/xx unknown
- 1980-09-04 BR BR8005645A patent/BR8005645A/pt not_active IP Right Cessation
- 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
- 1980-09-05 GR GR62813A patent/GR69955B/el unknown
- 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 CY CY1235A patent/CY1235A/en unknown
- 1980-09-08 AR AR282439A patent/AR228138A1/es active
-
1981
- 1981-02-13 OA OA57326A patent/OA06743A/xx unknown
-
1984
- 1984-03-01 KE KE3383A patent/KE3383A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
Non-Patent Citations (2)
| Title |
|---|
| ULLMANN: Encyklopädie der technischen Chemie, Bd.12, 1976, 4.Aufl., Verlag Chemie Weinheim, S.7,11,12 (Fungizide) * |
| WEGLER R.: Chemie der Pflanzenschutz und Schädlingsbekämpfungsmittel, Bd.4, 1977, Springer Verlag, S.164, 165, 208, 212-23, 213-217 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030026A1 (de) * | 1980-08-08 | 1981-03-26 | Sandoz-Patent-GmbH, 79539 Lörrach | Fungizide |
Also Published As
| Publication number | Publication date |
|---|---|
| GR69955B (enrdf_load_stackoverflow) | 1982-07-22 |
| AU545683B2 (en) | 1985-07-25 |
| IL60950A (en) | 1985-05-31 |
| GB2058071A (en) | 1981-04-08 |
| BR8005645A (pt) | 1981-03-17 |
| NL8004962A (nl) | 1981-03-10 |
| AR228138A1 (es) | 1983-01-31 |
| AU6194980A (en) | 1981-03-12 |
| KE3383A (en) | 1984-03-23 |
| ES494856A0 (es) | 1981-09-01 |
| ZA805450B (en) | 1981-08-26 |
| GB2058071B (en) | 1983-11-09 |
| CY1235A (en) | 1984-06-29 |
| OA06743A (fr) | 1982-06-30 |
| BE885117A (fr) | 1981-03-05 |
| IL60950A0 (en) | 1980-11-30 |
| IT1123564B (it) | 1986-04-30 |
| FR2464649A1 (fr) | 1981-03-20 |
| ES8106713A1 (es) | 1981-09-01 |
| JPH0240664B2 (enrdf_load_stackoverflow) | 1990-09-12 |
| CA1203539A (en) | 1986-04-22 |
| JPS5655381A (en) | 1981-05-15 |
| IT7925538A0 (it) | 1979-09-07 |
| FR2464649B1 (enrdf_load_stackoverflow) | 1983-07-08 |
| CH645513A5 (it) | 1984-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69028461T2 (de) | Triazin-derivate und unkrautvertilgungsmittel daraus | |
| DD142042A5 (de) | Verfahren zur herstellung von acylanilinen | |
| EP0212600A2 (de) | Neue Nitromethylen-Derivate | |
| DE2635663C2 (enrdf_load_stackoverflow) | ||
| DE3033161A1 (de) | N-aryl-n-acyl-3-amino-oxazolidin-2-one und diese enthaltende fungizide | |
| DE2757113C2 (enrdf_load_stackoverflow) | ||
| DD147043A5 (de) | Fungizide mittel | |
| DE2514402A1 (de) | Insektizide mittel | |
| DE3014353A1 (de) | Trisubstituierte cyanguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| DD150841A5 (de) | Insektizide mittel enthaltend salze von thiazolyliden-oxo-propionitrilen | |
| CH623458A5 (enrdf_load_stackoverflow) | ||
| CH520128A (de) | Verfahren zur Herstellung von Thioureidobenzolen sowie deren Verwendung in fungiziden und akariziden Mitteln | |
| DE3341343A1 (de) | Neue pyrimidin-4-one, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE2648074A1 (de) | N-chloracetyl-n-phenyl-alaninester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| DE2902832A1 (de) | Mikrobizide mittel | |
| DE2820361A1 (de) | Substituierte alkanyl-azolyl-oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide | |
| DE2702102A1 (de) | N-azolylacetyl-n-phenyl-alaninester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| DD298727A5 (de) | Mikrobizide mittel | |
| DD298723A5 (de) | Biozide mittel | |
| DE2902861A1 (de) | Mikrobizide mittel | |
| DE3139298A1 (de) | Neue fungizide alkylcarbazate und verfahren zu ihrerherstellung | |
| CH628206A5 (de) | Fungizides und nematizides mittel. | |
| DE2328728A1 (de) | Systemisch-fungizide mittel | |
| DE2065044B2 (de) | N-(3,5-dichlorphenyl)-oxa- und thiazolidin-derivate und ihre verwendung zur bekaempfung pflanzenpathogener pilze | |
| DE3638631A1 (de) | Pyrazoline, ihre herstellung und ihre verwendung als mittel mit insektizider und akarizider wirkung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT WEINHOL |
|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |