CH213902A - Process for the preparation of a thiuram sulfide heavy metal compound. - Google Patents
Process for the preparation of a thiuram sulfide heavy metal compound.Info
- Publication number
- CH213902A CH213902A CH213902DA CH213902A CH 213902 A CH213902 A CH 213902A CH 213902D A CH213902D A CH 213902DA CH 213902 A CH213902 A CH 213902A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- heavy metal
- metal compound
- preparation
- thiuram sulfide
- Prior art date
Links
- 229960002447 thiram Drugs 0.000 title claims description 9
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 title claims description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 title claims description 6
- 150000002736 metal compounds Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 4
- 150000001880 copper compounds Chemical class 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- -1 thiuram sulfides Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 241000722133 Tilletia Species 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung einer Thinramsulfid-Schwermetallverbindung. Es ist bekannt, zum Beizen von Getreidesaatgut Thiuramsulfide der allgemeinen Formel
EMI0001.0003
worin X - Alliyl oder Aralkyl Y = Alkyl, Aralkyl oder Aryl und n = 1-3 bedeuten, zu verwenden (E. P. Nr. 406996). Weiter ist bekannt, Tetraalliylthiuram- sulfide zur Bekämpfung von im Obstbau auf tretenden Pilzkrankheiten, wie Fusikladium etc., zu verwenden. Nach D. R. P.
Nr. 642"032 sollen die erwähnten Verbindungen als Saat gutbeizen zu wenig wirksam sein.
Es wurde nun die überraschende Beobach tung gemacht, dass Thiuramsulfide, und zwar sowohl symmetrische wie unsymmetrische von der allgemeinen Formel
EMI0001.0018
worin W, X, Y, Z Wasserstoff oder beliebige, aliphatische, araliphatische oder aromatische Reste sein können, sich mit Schwermetall salzen in neutralem bis saurem Illedium ohne Entschwefelung der organischen Komponente verbinden. Die Natur dieser Verbindungen ist nicht ganz abgeklärt, doch dürfte es sich um Komplexverbindungen, in einzelnen Fällen vielleicht auch um metallorganische Verbin dungen handeln.
In den fertigen Metall verbindungen kamt man auch nachträglich die vorhandenen Säurereste gegen andere aus tauschen oder auch noch andere Umsetzungen damit vornehmen. Gegenüber den Alkylthiuramsulfiden zei gen die erwähnten Schwermetallsalzverbin- dungen eine vielfach stärkere Wirkung als Fungizide und Saatgutbeizmittel.
Die nachfolgende Tabelle zeigt die be deutend verstärkte Wirkung der neuen Metall verbindungen gegen Tilletia
EMI0002.0005
<B>30'/.</B> <SEP> 20'/. <SEP> <B>15'/, <SEP> 10-/. <SEP> 50/, <SEP> 3-/.</B> <SEP> 2'/.
<tb> Tetramethylthiuramdisulfid <SEP> - <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++
<tb> Mercurichloridverbindung <SEP> -- <SEP> - <SEP> - <SEP> - <SEP> Cupricbloridverbindungen <SEP> - <SEP> -- <SEP> - <SEP> - <SEP> - <SEP> + <SEP> ++
<tb> Kupfersulfatverbindung <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> + <SEP> +
<tb> Cuprochloridverbindung <SEP> - <SEP> -- <SEP> - <SEP> - <SEP> - <SEP> - <SEP> Ferrichloridverbindung <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> + <SEP> +
<tb> Zinkchloridverbindung <SEP> - <SEP> Antimontrichloridverbindung <SEP> - <SEP> - <SEP> - <SEP> - <SEP> +++
<tb>
Bleiacetatverbindung <SEP> - <SEP> - <SEP> - <SEP> + <SEP> +
<tb> Erklärung: <SEP> - <SEP> kein <SEP> Wachstum, <SEP> + <SEP> schwaches <SEP> Wachstum, <SEP> ++ <SEP> mittleres <SEP> Wachstum,
<tb> +++ <SEP> starkes <SEP> Wachstum. Auch gegen andere Saatpilze wie z. B. Fusarium etc. zeigen die neuen Verbindungen eine ebenso gute Wirkung. Ferner ist zu er wähnen, dass sich die Blei-, Antimon- und Arsenverbindungen als Frassgifte eignen. Die Kupferverbindungen werden mit Vorteil als Fungizide im Obst- und Weinbau verwendet.
Ausserdem dürften einzelne Verbindungen, so die Ag-V erbindungen, als Desinfektionsmittel und als pharmazeutische Zwischenprodukte in Betracht kommen. Die Verbindungen können mit den üblichen Streckungs- und Verdün nungsmitteln coupiert werden, ausserdem kann man geeignete Netz- und Emulgiermittel zu setzen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Thiuram- sulfid-Schwermetallverbindung, dadurch ge kennzeichnet, dass Tetramethylthiuramdisulfid rnit Cuprichlorid in Gegenwart organischer Lösungsmittel in neutralem Medium zur Reak tion gebracht wird.
Die Kupferverbindung ist ein olivegrünes Pulver mit 29,8 % Kupfer- gehalt, in Wasser mit grüner Farbe teilweise löslich und beim trockenen Erwärmen be ständig. Es ist ein ausgezeichnet wirksames Saatgutbeizmittel.
<I>Beispiel:</I> 12 Teile Tetramethylthiuramdisulfid wer den in 150 Teilen Benzol gelöst und die etwas abgekühlte Lösung in eine solche von 20 Teilen Cuprichlorid (crist.) in 100 Teilen Alkohol gegossen. Die entstandene Fällung wird ab gesaugt, mit Alkohol und Benzol gut aus gewaschen und bei 30-401 C im Vakuum getrocknet. Olivegrünes Pulver, in Wasser teilweise mit grüner Farbe löslich. Die Ver- bindung ist beim trockenen Erwärmen be ständig.
Kupfergehalt 29,8 ,1o. Die Kupfer verbindung ist ein vorzügliches Saatgutbeiz mittel, das sowohl gegen Tilletia wie Fusarium und die andern Saatgutpilze ausgezeichnet wirksam ist.
Mit dem gleichen Resultat geht die Reak tion vor sich bei Anwendung einer acetonischen Cuprichloridlösung.
Process for producing a thinram sulfide heavy metal compound. It is known for the dressing of cereal seeds thiuram sulfide of the general formula
EMI0001.0003
where X - alliyl or aralkyl, Y = alkyl, aralkyl or aryl and n = 1-3, are to be used (E.P. No. 406996). It is also known that tetraalliylthiuram sulfide can be used to combat fungal diseases that occur in fruit growing, such as fusikladium, etc. According to D. R. P.
No. 642 "032, the compounds mentioned are said to be insufficiently effective as seed dressing.
The surprising observation has now been made that thiuram sulfides, both symmetrical and asymmetrical, of the general formula
EMI0001.0018
where W, X, Y, Z can be hydrogen or any aliphatic, araliphatic or aromatic radicals, combine with heavy metal salts in neutral to acidic medium without desulfurization of the organic component. The nature of these compounds has not been fully clarified, but they are likely to be complex compounds, and in individual cases perhaps also organometallic compounds.
In the finished metal compounds, the existing acid residues can also be subsequently exchanged for others or other conversions can be carried out with them. Compared to the alkylthiuram sulfides, the heavy metal salt compounds mentioned show a much stronger effect than fungicides and seed dressings.
The following table shows the significantly increased effect of the new metal compounds against Tilletia
EMI0002.0005
<B> 30 '/. </B> <SEP> 20' /. <SEP> <B> 15 '/, <SEP> 10- /. <SEP> 50 /, <SEP> 3- /. </B> <SEP> 2 '/.
<tb> Tetramethylthiuram disulfide <SEP> - <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++ <SEP> +++
<tb> Mercury chloride compound <SEP> - <SEP> - <SEP> - <SEP> - <SEP> Cupric chloride compound <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> + <SEP> ++
<tb> Copper sulfate compound <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> + <SEP> +
<tb> Cuprous chloride compound <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> - <SEP> ferric chloride compound <SEP> - <SEP> - <SEP> - <SEP> - < SEP> - <SEP> + <SEP> +
<tb> Zinc Chloride Compound <SEP> - <SEP> Antimony Trichloride Compound <SEP> - <SEP> - <SEP> - <SEP> - <SEP> +++
<tb>
Lead acetate compound <SEP> - <SEP> - <SEP> - <SEP> + <SEP> +
<tb> Explanation: <SEP> - <SEP> no <SEP> growth, <SEP> + <SEP> weak <SEP> growth, <SEP> ++ <SEP> medium <SEP> growth,
<tb> +++ <SEP> strong <SEP> growth. Also against other seed fungi such. B. Fusarium etc. show the new compounds an equally good effect. It should also be mentioned that the lead, antimony and arsenic compounds are suitable as food poisons. The copper compounds are used with advantage as fungicides in fruit growing and viticulture.
In addition, individual compounds, such as the Ag compounds, may be used as disinfectants and as pharmaceutical intermediates. The compounds can be couped with the usual extenders and diluents, and suitable wetting and emulsifying agents can also be added.
The subject matter of the present patent is a process for the production of a thiuram sulfide heavy metal compound, characterized in that tetramethylthiuram disulfide is reacted with cuprichloride in the presence of organic solvents in a neutral medium.
The copper compound is an olive green powder with 29.8% copper content, partially soluble in water with a green color and permanent when heated dry. It is an excellent seed dressing agent.
<I> Example: </I> 12 parts of tetramethylthiuram disulfide are dissolved in 150 parts of benzene and the somewhat cooled solution is poured into one of 20 parts of cuprichloride (crist.) In 100 parts of alcohol. The resulting precipitate is filtered off with suction, washed well with alcohol and benzene and dried at 30-401 ° C. in vacuo. Olive green powder, partially soluble in water with a green color. The connection is permanent when heated dry.
Copper content 29.8, 1o. The copper compound is an excellent seed dressing that is extremely effective against both Tilletia and Fusarium and the other seed fungi.
The reaction proceeds with the same result when using an acetone cuprichloride solution.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213902T | 1939-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213902A true CH213902A (en) | 1941-03-31 |
Family
ID=4448461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH213902D CH213902A (en) | 1939-07-03 | 1939-07-03 | Process for the preparation of a thiuram sulfide heavy metal compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH213902A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1149940B (en) * | 1959-07-13 | 1963-06-06 | Morton Salt Company | Method of treating seeds |
-
1939
- 1939-07-03 CH CH213902D patent/CH213902A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1149940B (en) * | 1959-07-13 | 1963-06-06 | Morton Salt Company | Method of treating seeds |
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