DE1695847C3 - 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole - Google Patents
2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazoleInfo
- Publication number
- DE1695847C3 DE1695847C3 DE1695847A DESC040854A DE1695847C3 DE 1695847 C3 DE1695847 C3 DE 1695847C3 DE 1695847 A DE1695847 A DE 1695847A DE SC040854 A DESC040854 A DE SC040854A DE 1695847 C3 DE1695847 C3 DE 1695847C3
- Authority
- DE
- Germany
- Prior art keywords
- sulfonyl
- thiadiazole
- propyl
- bis
- methylpropyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 3-chloropropyl Chemical group 0.000 claims description 11
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000011717 all-trans-retinol Substances 0.000 claims description 5
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 241001281803 Plasmopara viticola Species 0.000 claims description 3
- 241000228452 Venturia inaequalis Species 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 241000123650 Botrytis cinerea Species 0.000 claims description 2
- 241000427940 Fusarium solani Species 0.000 claims description 2
- 241000813090 Rhizoctonia solani Species 0.000 claims description 2
- 241000398309 Satyrium ilicis Species 0.000 claims description 2
- 231100000676 disease causative agent Toxicity 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 229960000583 acetic acid Drugs 0.000 claims 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 241000584609 Alternaria consortialis Species 0.000 claims 1
- 241000228245 Aspergillus niger Species 0.000 claims 1
- VIONLWCXICLRBZ-UHFFFAOYSA-N CCCC1=NN=CS1=S(=O)=O Chemical compound CCCC1=NN=CS1=S(=O)=O VIONLWCXICLRBZ-UHFFFAOYSA-N 0.000 claims 1
- 241001529387 Colletotrichum gloeosporioides Species 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 229940022682 acetone Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000012286 potassium permanganate Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 22
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 9
- VNRIHEIPDHEQIA-UHFFFAOYSA-N 1-sulfonyl-1,3,4-thiadiazole Chemical compound O=S(=O)=S1C=NN=C1 VNRIHEIPDHEQIA-UHFFFAOYSA-N 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 241000233626 Plasmopara Species 0.000 description 2
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 230000004763 spore germination Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 241000222199 Colletotrichum Species 0.000 description 1
- 241000489964 Fusicladium Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000371621 Stemphylium Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000004362 fungal culture Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000011835 investigation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1695847A DE1695847C3 (de) | 1967-06-09 | 1967-06-09 | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
| AT443168A AT281501B (de) | 1967-06-09 | 1968-05-08 | Fungizide Mittel |
| DK224068AA DK117604B (da) | 1967-06-09 | 1968-05-14 | Fungicidt middel. |
| BG009998A BG15729A3 (bg) | 1967-06-09 | 1968-05-18 | Метод за получаване на нови 1,3,4-тиадиазоли |
| SE07193/68A SE347640B (enExample) | 1967-06-09 | 1968-05-29 | |
| CS399068A CS157035B2 (enExample) | 1967-06-09 | 1968-05-30 | |
| YU1277/68A YU32378B (en) | 1967-06-09 | 1968-06-03 | Postupak za dobijanje novih 1, 3, 4-tiadiazola |
| IL30136A IL30136A (en) | 1967-06-09 | 1968-06-06 | Fungicidally active 1,3,4-thiadiazoles |
| ES354798A ES354798A1 (es) | 1967-06-09 | 1968-06-07 | Procedimiento de fabricacion de nuevos compuestos fungici- das. |
| BE716257D BE716257A (enExample) | 1967-06-09 | 1968-06-07 | |
| FR154185A FR1568552A (enExample) | 1967-06-09 | 1968-06-07 | |
| NL6808106.A NL161145C (nl) | 1967-06-09 | 1968-06-08 | Werkwijze voor het bereiden van fungicide-preparaten en daarvoor geschikte actieve verbindingen. |
| CH855568A CH502370A (de) | 1967-06-09 | 1968-06-10 | Verfahren zur Herstellung substituierter 1,3,4-Thiadiazole und deren Verwendung in fungiziden Mitteln |
| GB27558/68A GB1237436A (en) | 1967-06-09 | 1968-06-10 | Fungicidally active 1,3,4-thiadiazoles |
| BG010850A BG15728A3 (bg) | 1967-06-09 | 1968-10-19 | Фунгицидни средства |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1695847A DE1695847C3 (de) | 1967-06-09 | 1967-06-09 | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1695847A1 DE1695847A1 (de) | 1971-05-13 |
| DE1695847B2 DE1695847B2 (de) | 1977-12-29 |
| DE1695847C3 true DE1695847C3 (de) | 1978-09-21 |
Family
ID=7435901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1695847A Expired DE1695847C3 (de) | 1967-06-09 | 1967-06-09 | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT281501B (enExample) |
| BE (1) | BE716257A (enExample) |
| BG (2) | BG15729A3 (enExample) |
| CH (1) | CH502370A (enExample) |
| CS (1) | CS157035B2 (enExample) |
| DE (1) | DE1695847C3 (enExample) |
| DK (1) | DK117604B (enExample) |
| ES (1) | ES354798A1 (enExample) |
| FR (1) | FR1568552A (enExample) |
| GB (1) | GB1237436A (enExample) |
| IL (1) | IL30136A (enExample) |
| NL (1) | NL161145C (enExample) |
| SE (1) | SE347640B (enExample) |
| YU (1) | YU32378B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1093452B (de) * | 1957-07-05 | 1960-11-24 | Berker Geb | Sicherheitssteckdose |
| DE1139173B (de) * | 1961-06-05 | 1962-11-08 | Elisabeth Mausz | Schutzkontaktsteckdose mit Schalteinrichtung |
| DE2044442C2 (de) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
| DE2526308C2 (de) * | 1975-06-12 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | 2-Halogen-5-trichlormethyl-1,3,4-thiadiazole |
| US4432847A (en) * | 1976-07-29 | 1984-02-21 | Standard Oil Company (Indiana) | Poly sulfoxides from 1,3,4-thiadiazole-2,5-dithiol |
| DE2933008A1 (de) * | 1979-08-13 | 1981-04-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
| ES2034371T3 (es) * | 1987-12-18 | 1993-04-01 | Ciba-Geigy Ag | Procedimiento para la preparacion de 2-tio-5-difluormetiltio-1,3,4-tiadiazol y productos nematocidas. |
| DE3838432A1 (de) * | 1988-11-12 | 1990-05-17 | Bayer Ag | 2,5-disubstituierte 1,3,4-thiadiazol-derivate, ein verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
-
1967
- 1967-06-09 DE DE1695847A patent/DE1695847C3/de not_active Expired
-
1968
- 1968-05-08 AT AT443168A patent/AT281501B/de not_active IP Right Cessation
- 1968-05-14 DK DK224068AA patent/DK117604B/da not_active IP Right Cessation
- 1968-05-18 BG BG009998A patent/BG15729A3/bg unknown
- 1968-05-29 SE SE07193/68A patent/SE347640B/xx unknown
- 1968-05-30 CS CS399068A patent/CS157035B2/cs unknown
- 1968-06-03 YU YU1277/68A patent/YU32378B/xx unknown
- 1968-06-06 IL IL30136A patent/IL30136A/en unknown
- 1968-06-07 ES ES354798A patent/ES354798A1/es not_active Expired
- 1968-06-07 BE BE716257D patent/BE716257A/xx not_active IP Right Cessation
- 1968-06-07 FR FR154185A patent/FR1568552A/fr not_active Expired
- 1968-06-08 NL NL6808106.A patent/NL161145C/xx not_active IP Right Cessation
- 1968-06-10 GB GB27558/68A patent/GB1237436A/en not_active Expired
- 1968-06-10 CH CH855568A patent/CH502370A/de not_active IP Right Cessation
- 1968-10-19 BG BG010850A patent/BG15728A3/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695847A1 (de) | 1971-05-13 |
| CH502370A (de) | 1971-01-31 |
| DE1695847B2 (de) | 1977-12-29 |
| NL6808106A (enExample) | 1968-12-10 |
| BG15728A3 (bg) | 1975-12-15 |
| AT281501B (de) | 1970-05-25 |
| BG15729A3 (bg) | 1975-12-15 |
| BE716257A (enExample) | 1968-12-09 |
| YU32378B (en) | 1974-10-31 |
| NL161145C (nl) | 1980-01-15 |
| DK117604B (da) | 1970-05-11 |
| GB1237436A (en) | 1971-06-30 |
| NL161145B (nl) | 1979-08-15 |
| IL30136A0 (en) | 1968-08-22 |
| YU127768A (en) | 1974-04-30 |
| CS157035B2 (enExample) | 1974-08-23 |
| SE347640B (enExample) | 1972-08-14 |
| ES354798A1 (es) | 1969-11-01 |
| IL30136A (en) | 1972-07-26 |
| FR1568552A (enExample) | 1969-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |