DE2515669A1 - Chlor-pyridylthioalkyl-thiocyanate, sowie verfahren zu ihrer herstellung - Google Patents
Chlor-pyridylthioalkyl-thiocyanate, sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE2515669A1 DE2515669A1 DE19752515669 DE2515669A DE2515669A1 DE 2515669 A1 DE2515669 A1 DE 2515669A1 DE 19752515669 DE19752515669 DE 19752515669 DE 2515669 A DE2515669 A DE 2515669A DE 2515669 A1 DE2515669 A1 DE 2515669A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- reaction
- trichloro
- compound
- compounds
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000000203 mixture Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- -1 3,5,6-trichloro-2- (thiocyanatomethylthio) pyridine Chemical compound 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical compound [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003567 thiocyanates Chemical class 0.000 description 2
- DBPSVFRRAOJDIY-UHFFFAOYSA-N 2-sulfinyl-1h-pyridine Chemical class O=S=C1C=CC=CN1 DBPSVFRRAOJDIY-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241001342895 Chorus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 240000001536 Prunus fruticosa Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US460833A US3895015A (en) | 1974-04-15 | 1974-04-15 | Chloropyridyl thioalkylthio cyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2515669A1 true DE2515669A1 (de) | 1975-10-23 |
Family
ID=23830251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752515669 Pending DE2515669A1 (de) | 1974-04-15 | 1975-04-10 | Chlor-pyridylthioalkyl-thiocyanate, sowie verfahren zu ihrer herstellung |
Country Status (7)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758482A (en) * | 1971-06-30 | 1973-09-11 | Dow Chemical Co | Halopyridyl thiocyanates |
| US3787425A (en) * | 1973-02-09 | 1974-01-22 | Dow Chemical Co | Halopyridyl thiocyanates |
| US3787422A (en) * | 1973-02-09 | 1974-01-22 | Dow Chemical Co | Halopyridyl thiocyanates |
-
1974
- 1974-04-15 US US460833A patent/US3895015A/en not_active Expired - Lifetime
-
1975
- 1975-04-07 ES ES436371A patent/ES436371A1/es not_active Expired
- 1975-04-07 NL NL7504107A patent/NL7504107A/xx unknown
- 1975-04-08 CA CA224,064A patent/CA1027567A/en not_active Expired
- 1975-04-10 JP JP50043856A patent/JPS50140457A/ja active Pending
- 1975-04-10 DE DE19752515669 patent/DE2515669A1/de active Pending
- 1975-04-14 NO NO751312A patent/NO751312L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7504107A (nl) | 1975-10-17 |
| JPS50140457A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-11 |
| ES436371A1 (es) | 1977-01-16 |
| US3895015A (en) | 1975-07-15 |
| CA1027567A (en) | 1978-03-07 |
| NO751312L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2212268B2 (de) | N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen | |
| DE1542879B2 (de) | Verwendung von derivaten des 2,3- dihydro-2,2-dimethyl-7-benzofuranyl-carbamats als nematizide | |
| DE1620161C3 (de) | 1,3,4-Oxadiazolderivate, Verfahren zu deren Herstellung und insektizide Mittel | |
| DE2506275A1 (de) | Cyanophenyl-sulfoxide und -sulfone | |
| DE2515669A1 (de) | Chlor-pyridylthioalkyl-thiocyanate, sowie verfahren zu ihrer herstellung | |
| DE2166953C3 (de) | Antimikrobielles Mittel auf der Basis von Jodoniumsalzen | |
| DE1953422C3 (de) | Fungicides Mittel für Landwirtschaft und Gartenbau | |
| DE2349474C2 (de) | Tri(cylcohexylalkyl)zinnverbindungen und ihre Verwendung zur Bekämpfung von Pilzen und Milben | |
| DE2515773A1 (de) | Halogen-bis-(thiocyanatomethylthio)- pyridine, sowie verfahren zur herstellung derselben | |
| DE2735057A1 (de) | Verfahren zur herstellung von triorganozinnhalogeniden | |
| DE2045098C3 (de) | N-substituierte N-Thioformylhydroxylamine, Verfahren zu ihrer Herstellung und ihre Verwendung als antibacterielles oder fungicides Mittel | |
| DE2519085C3 (de) | Substituierte Benzolmethanolverbindungen und diese enthaltende herbizide Mittel | |
| DE2244745C3 (de) | Thiocarbaminsäureester, ihre Herstellung und diese Ester enthaltende pestizide Mittel | |
| DE1567046A1 (de) | Parasitizides,insbesondere fungizides Mittel | |
| DE2441476A1 (de) | Triorganozinn enthaltende schaedlingsbekaempfungsmittel | |
| DE2548898A1 (de) | Benzothiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE2145733C3 (de) | Thienyl(2)-jodoniumsalze und diese enthaltende antimikrobielle Mittel | |
| DE2515631A1 (de) | Pyridyl-thiomethyl-thiocyanate, sowie verfahren zur herstellung derselben | |
| DE1542849A1 (de) | Fungizide Mittel | |
| DE1542879C3 (de) | Verwendung von Derivaten des 23-Dihydro-2^-dimethyl-7-benzofuranyl-carbamats als Nematozide | |
| DE2515668A1 (de) | Halogen-pyridyl-thioalkyl-thiocyanate sowie verfahren zu ihrer herstellung | |
| DE1768736C (de) | N Acyl N hydrocarbylsulfenyl harn stoffe und diese enthaltende Fungizide | |
| AT339662B (de) | Insektizide, akarizide und nematizide mittel | |
| AT233319B (de) | Fungizide Mittel | |
| AT345816B (de) | Verfahren zur herstellung von neuen thiadiazolylimidazolinonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |