CA1068712A - Combinations containing 2,5-substituted 1,3,4-oxadiazoles as plant disease control agents and a process for the manufacture of same - Google Patents
Combinations containing 2,5-substituted 1,3,4-oxadiazoles as plant disease control agents and a process for the manufacture of sameInfo
- Publication number
- CA1068712A CA1068712A CA245,618A CA245618A CA1068712A CA 1068712 A CA1068712 A CA 1068712A CA 245618 A CA245618 A CA 245618A CA 1068712 A CA1068712 A CA 1068712A
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- manufacture
- compounds
- compound
- oxadiazoles
- 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
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 201000010099 disease Diseases 0.000 title abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 4
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- PXMPLVVRNMMKOV-UHFFFAOYSA-N n-phenyl-5-(9h-xanthen-9-yl)-1,3,4-oxadiazol-2-amine Chemical compound N=1N=C(C2C3=CC=CC=C3OC3=CC=CC=C32)OC=1NC1=CC=CC=C1 PXMPLVVRNMMKOV-UHFFFAOYSA-N 0.000 claims description 3
- RTCIJXXXZDUYDV-UHFFFAOYSA-N 5-(9h-fluoren-9-yl)-n-phenyl-1,3,4-oxadiazol-2-amine Chemical compound N=1N=C(C2C3=CC=CC=C3C3=CC=CC=C32)OC=1NC1=CC=CC=C1 RTCIJXXXZDUYDV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 16
- 230000000855 fungicidal effect Effects 0.000 abstract description 9
- 239000004480 active ingredient Substances 0.000 abstract description 8
- 239000000839 emulsion Substances 0.000 abstract description 6
- -1 dusts Substances 0.000 abstract description 3
- 241000233622 Phytophthora infestans Species 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000007921 spray Substances 0.000 abstract description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 239000004141 Sodium laurylsulphate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000000969 carrier Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DGUDFLOTFOKYEG-UHFFFAOYSA-N 1-(9h-fluorene-9-carbonylamino)-3-phenylurea Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1C(=O)NNC(=O)NC1=CC=CC=C1 DGUDFLOTFOKYEG-UHFFFAOYSA-N 0.000 description 1
- HERDEDRJALXJRQ-UHFFFAOYSA-N 1-phenyl-3-(9h-xanthene-9-carbonylamino)urea Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)NNC(=O)NC1=CC=CC=C1 HERDEDRJALXJRQ-UHFFFAOYSA-N 0.000 description 1
- QTUDOGMWPNUCEQ-UHFFFAOYSA-N 9h-fluorene-9-carbohydrazide Chemical compound C1=CC=C2C(C(=O)NN)C3=CC=CC=C3C2=C1 QTUDOGMWPNUCEQ-UHFFFAOYSA-N 0.000 description 1
- VDVNAWMSFFMKDT-UHFFFAOYSA-N 9h-xanthene-9-carbohydrazide Chemical compound C1=CC=C2C(C(=O)NN)C3=CC=CC=C3OC2=C1 VDVNAWMSFFMKDT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 229940098458 powder spray Drugs 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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)
- Character Discrimination (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75CI00001544A HU171563B (hu) | 1975-02-13 | 1975-02-13 | Fungicidnaja kompozicija soderzhahhaja 2,5-zamehhennye 13,4-oksadiazolov i sposob poluchenija ikh |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068712A true CA1068712A (en) | 1979-12-25 |
Family
ID=10994552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,618A Expired CA1068712A (en) | 1975-02-13 | 1976-02-12 | Combinations containing 2,5-substituted 1,3,4-oxadiazoles as plant disease control agents and a process for the manufacture of same |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS51105068A (cs) |
| AT (1) | AT346645B (cs) |
| BE (1) | BE838577A (cs) |
| CA (1) | CA1068712A (cs) |
| CS (1) | CS194949B1 (cs) |
| DD (1) | DD124045A1 (cs) |
| DK (1) | DK56776A (cs) |
| ES (1) | ES445141A1 (cs) |
| FI (1) | FI760343A7 (cs) |
| FR (1) | FR2300504A1 (cs) |
| GB (1) | GB1518044A (cs) |
| HU (1) | HU171563B (cs) |
| IL (1) | IL48967A (cs) |
| NO (1) | NO760451L (cs) |
| PL (1) | PL99166B1 (cs) |
| SE (1) | SE7601450L (cs) |
| SU (1) | SU638236A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113979964A (zh) * | 2021-11-29 | 2022-01-28 | 贵州大学 | 一类含1,3,4-噁二唑硫醚的苯丙氨酸衍生物的制备及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1452710A (fr) * | 1964-07-21 | 1966-04-15 | Basf Ag | Oxdiazoles-1-3-4 et procédé pour leur production |
| DE1670702A1 (de) * | 1966-05-25 | 1970-11-12 | Bayer Ag | Verfahren zur Herstellung von Aminooxadiazolen |
-
1975
- 1975-02-13 HU HU75CI00001544A patent/HU171563B/hu unknown
-
1976
- 1976-02-04 IL IL48967A patent/IL48967A/xx unknown
- 1976-02-06 AT AT82376A patent/AT346645B/de not_active IP Right Cessation
- 1976-02-10 SE SE7601450A patent/SE7601450L/xx unknown
- 1976-02-11 FR FR7603725A patent/FR2300504A1/fr active Granted
- 1976-02-11 DD DD191189A patent/DD124045A1/xx unknown
- 1976-02-12 NO NO760451A patent/NO760451L/no unknown
- 1976-02-12 CA CA245,618A patent/CA1068712A/en not_active Expired
- 1976-02-12 FI FI760343A patent/FI760343A7/fi not_active Application Discontinuation
- 1976-02-12 GB GB5624/76A patent/GB1518044A/en not_active Expired
- 1976-02-12 DK DK56776*#A patent/DK56776A/da unknown
- 1976-02-12 JP JP51013320A patent/JPS51105068A/ja active Pending
- 1976-02-13 CS CS76961A patent/CS194949B1/cs unknown
- 1976-02-13 BE BE164333A patent/BE838577A/xx unknown
- 1976-02-13 SU SU762322551A patent/SU638236A3/ru active
- 1976-02-13 PL PL1976187217A patent/PL99166B1/pl unknown
- 1976-02-13 ES ES445141A patent/ES445141A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA82376A (de) | 1978-03-15 |
| CS194949B1 (en) | 1979-12-31 |
| ES445141A1 (es) | 1977-08-16 |
| JPS51105068A (cs) | 1976-09-17 |
| PL99166B1 (pl) | 1978-06-30 |
| NO760451L (cs) | 1976-08-16 |
| BE838577A (fr) | 1976-05-28 |
| AT346645B (de) | 1978-11-27 |
| IL48967A (en) | 1978-08-31 |
| FI760343A7 (cs) | 1976-08-14 |
| FR2300504B1 (cs) | 1980-02-29 |
| GB1518044A (en) | 1978-07-19 |
| FR2300504A1 (fr) | 1976-09-10 |
| IL48967A0 (en) | 1976-04-30 |
| SU638236A3 (ru) | 1978-12-15 |
| SE7601450L (sv) | 1976-08-14 |
| DK56776A (da) | 1976-08-14 |
| DD124045A1 (cs) | 1977-02-02 |
| HU171563B (hu) | 1978-02-28 |
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