DE2120666C3 - 2 Sulfonyhmido 4,5 dicyan 1,3 dithiacyclopentene, Verfahren zu deren Herstellung und deren Verwendung als bakten cide und fungicide Mittel - Google Patents
2 Sulfonyhmido 4,5 dicyan 1,3 dithiacyclopentene, Verfahren zu deren Herstellung und deren Verwendung als bakten cide und fungicide MittelInfo
- Publication number
- DE2120666C3 DE2120666C3 DE2120666A DE2120666A DE2120666C3 DE 2120666 C3 DE2120666 C3 DE 2120666C3 DE 2120666 A DE2120666 A DE 2120666A DE 2120666 A DE2120666 A DE 2120666A DE 2120666 C3 DE2120666 C3 DE 2120666C3
- Authority
- DE
- Germany
- Prior art keywords
- none
- dicyan
- dithiacyclopentene
- dicyano
- crystals
- 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
- 230000000844 anti-bacterial effect Effects 0.000 title description 8
- 239000003899 bactericide agent Substances 0.000 title description 7
- 239000000417 fungicide Substances 0.000 title description 7
- 238000000034 method Methods 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- XWYAZJBWUYNBSL-UHFFFAOYSA-N 1,3-dithiole-4,5-dicarbonitrile Chemical compound N#CC1=C(C#N)SCS1 XWYAZJBWUYNBSL-UHFFFAOYSA-N 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000006378 damage Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 208000014674 injury Diseases 0.000 description 8
- 239000012496 blank sample Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- UQUADKBSFUWAAS-UHFFFAOYSA-N 2,3-bis(sulfanyl)butanedinitrile Chemical compound N#CC(S)C(S)C#N UQUADKBSFUWAAS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- DLGFTUQMUOOJRY-UHFFFAOYSA-N 2,2,3-triethyloxolane Chemical compound CCC1CCOC1(CC)CC DLGFTUQMUOOJRY-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241001140399 Elsinoe sp. Species 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 241000899403 Phaeoisariopsis Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- CXMYOMKBXNPDIW-UHFFFAOYSA-N cyclopenten-1-ylbenzene Chemical compound C1CCC=C1C1=CC=CC=C1 CXMYOMKBXNPDIW-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7495670A JPS4811014B1 (enExample) | 1970-08-28 | 1970-08-28 | |
| JP11573970A JPS4811938B1 (enExample) | 1970-12-23 | 1970-12-23 | |
| JP12129670A JPS4811939B1 (enExample) | 1970-12-29 | 1970-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2120666A1 DE2120666A1 (enExample) | 1972-03-09 |
| DE2120666B2 DE2120666B2 (de) | 1973-04-19 |
| DE2120666C3 true DE2120666C3 (de) | 1973-11-15 |
Family
ID=27301663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2120666A Expired DE2120666C3 (de) | 1970-08-28 | 1971-04-27 | 2 Sulfonyhmido 4,5 dicyan 1,3 dithiacyclopentene, Verfahren zu deren Herstellung und deren Verwendung als bakten cide und fungicide Mittel |
Country Status (9)
| Country | Link |
|---|---|
| BR (1) | BR7104214D0 (enExample) |
| DD (2) | DD101269A5 (enExample) |
| DE (1) | DE2120666C3 (enExample) |
| ES (1) | ES393767A1 (enExample) |
| FR (1) | FR2089706A5 (enExample) |
| GB (1) | GB1327123A (enExample) |
| IL (1) | IL36430A (enExample) |
| NL (1) | NL7104313A (enExample) |
| PL (1) | PL82087B1 (enExample) |
-
1971
- 1971-03-17 IL IL36430A patent/IL36430A/xx unknown
- 1971-03-31 NL NL7104313A patent/NL7104313A/xx unknown
- 1971-04-15 FR FR7113347A patent/FR2089706A5/fr not_active Expired
- 1971-04-27 DE DE2120666A patent/DE2120666C3/de not_active Expired
- 1971-05-20 GB GB1593471*[A patent/GB1327123A/en not_active Expired
- 1971-07-02 BR BR004214/71A patent/BR7104214D0/pt unknown
- 1971-07-30 ES ES393767A patent/ES393767A1/es not_active Expired
- 1971-08-26 PL PL1971150191A patent/PL82087B1/pl unknown
- 1971-08-27 DD DD157376A patent/DD101269A5/xx unknown
- 1971-08-27 DD DD170830*A patent/DD106648A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1327123A (en) | 1973-08-15 |
| DD106648A5 (enExample) | 1974-06-20 |
| IL36430A (en) | 1974-03-14 |
| DE2120666A1 (enExample) | 1972-03-09 |
| ES393767A1 (es) | 1973-09-01 |
| DD101269A5 (enExample) | 1973-11-05 |
| IL36430A0 (en) | 1971-05-26 |
| FR2089706A5 (enExample) | 1972-01-07 |
| DE2120666B2 (de) | 1973-04-19 |
| NL7104313A (enExample) | 1972-03-01 |
| BR7104214D0 (pt) | 1973-05-10 |
| PL82087B1 (enExample) | 1975-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |