DE1020481B - Fungicidal agent - Google Patents
Fungicidal agentInfo
- Publication number
- DE1020481B DE1020481B DEB31000A DEB0031000A DE1020481B DE 1020481 B DE1020481 B DE 1020481B DE B31000 A DEB31000 A DE B31000A DE B0031000 A DEB0031000 A DE B0031000A DE 1020481 B DE1020481 B DE 1020481B
- Authority
- DE
- Germany
- Prior art keywords
- diphenylene
- salt
- bis
- fungicidal
- agent according
- 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
- 239000000417 fungicide Substances 0.000 title claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical group 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000000428 dust Substances 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000003595 mist Substances 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- -1 aliphatic amines Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/16—Salts of dithiocarbamic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fungizides Mittel Die Verwendung von Alkylenbisdithiocarbamaten nach der allgemeinen Formel in der R eine zweiwertige Kohlenwasserstoffgruppe oder eine zweiwertige aliphatische Kette mit mehr als 3 Kohlenstoffatomen darstellt, die durch mindestens 1 Stickstoffatom zwecks Bildung von Alkylengruppen mit mindestens je 2 Kohlenstoffatomen voneinander getrennt sind, R' und R" jedes für sich Wasserstoff oder in Verbindung miteinander eine zweiwertige Kohlenwasserstoffgruppe darstellen und M eine salzbildende Gruppe oder ein Metall darstellt, als fungizide Mittel ist bekannt.Fungicidal agent The use of Alkylenbisdithiocarbamaten according to the general formula in which R represents a divalent hydrocarbon group or a divalent aliphatic chain with more than 3 carbon atoms, which are separated from one another by at least 1 nitrogen atom for the purpose of forming alkylene groups with at least 2 carbon atoms each, R 'and R "are each hydrogen or in combination with one another represent a divalent hydrocarbon group, and M represents a salt-forming group or a metal, as fungicidal agents are known.
Verbindungen der obigen Formel lassen sich durch Umsetzung eines Polyamins mit Schwefelkohlenstoff im allgemeinen in Gegenwart einer freien Base herstellen. Diese Herstellungsweise gilt aber nur für aliphatische Amine, während die meisten Diamine der aromatischen Reihe allgemein nur mit einer Aminogruppe mit Schwefelkohlenstoff in Gegenwart einer starken Base unter Bildung einer Dithiocarbaminverbindung reagieren. Die Reaktion der anderen Aminogruppe verläuft im allgemeinen in der Richtung, daB sich unter Abspaltung von H2 S Phenylisothiocyanat bildet Diamine der Diphenylgruppe, wie Benzidin und seine Derivate, reagieren mit Schwefelkohlenstoff jedoch in dem Sinne, daB sich Verbindungen nach folgender Formel bilden: Man bezeichnet sie als Diphenylen-bis-dithiocarbamate. In der Formel III bedeutet R Wasserstoff, Halogen, eine Nitro- oder Aminogruppe, einen Alkyl- oder Aryl-bzw. einen Acylrest, Me einen Metallrest oder eine salzbildende Gruppe. Nach der allgemeinen Formel kommen z. B. folgende Verbindungen in Frage: 1. diphenylen-bis-dithiocarbamidsaures Zink 2. 2,2'dibrom-diphenylen-bis-dithiocarbamidsaures Zink 3. 2-nitro-diphenylen-bis-dithiocarbamidsaures Natrium 4. 3-nitro-diphenylen-bis-dithiocarbamidsaures Ammonium 5. 3,5,3',5'-tetrachlor-diphenylen-bis-dithiocarbamidsaures Mangan 6. 3,3'-dimethyl-diphenylen-bisdithiocarbamidsaures Zink 7. 3,3'-dimethoxy-diphenylen-bisdithiocarbamidsaures Zink B. 2,2'-diäthy 1-diphenylen-bis-dithiocarbamidsaures Natrium Mit zweiwertigen Metallen bilden sich in Wasser schwerlösliche Verbindungen, während Alkali- bzw. Ammoniumverbindungen Salze bilden, die verhältnismäßig leichter in Wasser löslich sind. Diese Salze besitzen fungizide Wirkung und können, ob löslich oder unlöslich, in Wasser suspendiert werden. Mit einem Trägerstoff, wie Talkum, Kaolin, können sie gemischt und dann als Stäube- oder Spritzmittel verwendet werden. Überraschenderweise besitzen, wie durch Versuche g2-funden wurde, die Diphenylen-bis-dithiocarbamate eine starke Fungizide Wirkung, die zum Teil größer als die der Alkylen-bis-dithiocarbamate ist.Compounds of the above formula can generally be prepared by reacting a polyamine with carbon disulfide in the presence of a free base. However, this method of preparation only applies to aliphatic amines, while most diamines of the aromatic series generally only react with one amino group with carbon disulfide in the presence of a strong base to form a dithiocarbamine compound. The reaction of the other amino group generally proceeds in the direction that phenyl isothiocyanate is formed with elimination of H2 S Diamines of the diphenyl group, such as benzidine and its derivatives, react with carbon disulfide in the sense that compounds are formed according to the following formula: They are called diphenylene-bis-dithiocarbamates. In formula III, R denotes hydrogen, halogen, a nitro or amino group, an alkyl or aryl or. an acyl radical, Me a metal radical or a salt-forming group. According to the general formula z. B. the following compounds in question: 1. Diphenylene-bis-dithiocarbamic acid zinc 2. Zinc 2,2'-dibromo-diphenylene-bis-dithiocarbamic acid 3. Sodium 2-nitro-diphenylene-bis-dithiocarbamic acid 4. 3-nitro-diphenylene-bis-dithiocarbamic acid ammonium 5. 3,5,3 ', 5'-tetrachloro-diphenylene-bis-dithiocarbamic acid manganese 6. Zinc 3,3'-dimethyl-diphenylene-bisdithiocarbamic acid 7. Zinc 3,3'-dimethoxy-diphenylene-bisdithiocarbamic acid B. 2,2'-diethy 1-diphenylen-bis-dithiocarbamic acid sodium With divalent metals, compounds that are sparingly soluble in water are formed, while alkali or ammonium compounds form salts that are relatively more easily soluble in water. These salts have a fungicidal effect and, whether soluble or insoluble, can be suspended in water. They can be mixed with a carrier such as talc or kaolin and then used as dust or spray. Surprisingly, as was found by experiments g2, the diphenylene-bis-dithiocarbamates have a strong fungicidal action which is in some cases greater than that of the alkylene-bis-dithiocarbamates.
Es zeigte sich weiter, daß die Verträglichkeit der Diphenylenverbindungen eine bessere ist, im Vergleich mit den bekannten Alkylenverbindungen. Vermutlich sind diese unerwarteten Wirkungen durch das Vorhandensein der Benzidin-Gruppe zu erklären, die die Molekularstruktur dieser fungiziden Verbindung maßgebend beeinflußt und daher so zur Steigerung der Verträglichkeit in der Anwendung bei lebenden Pflanzen und der Fungiziden Wirkungsbreite maßgebend beiträgt.It was also shown that the compatibility of the diphenylene compounds is a better one in comparison with the known alkylene compounds. Allegedly these unexpected effects are due to the presence of the benzidine group too explain, which significantly influences the molecular structure of this fungicidal compound and therefore so as to increase the compatibility in use with living plants and the fungicidal range of action makes a decisive contribution.
Auch zeichnen sich die Salze der Diphenylen-bisdithiocarbamidsäure durch größere Beständigkeit aus als z. B. die in der USA.-Patentschrift 2 317 765 beschriebenen Verbindungen.The salts of diphenylene bisdithiocarbamic acid are also notable by greater resistance than z. See, for example, U.S. Patent 2,317,765 connections described.
Schon bei der Herstellung zeigen die Derivate des Benzidins in Gegenwart von Wasser eine größere Stabilität, so daß deren Trocknung nicht mit den üblichen Vorsichtsmaßregeln vorgenommen zu werden braucht als bei anderen Bis-dithiocarbaminsäurederivaten. Die trockene bzw. trocken vermahlene und verschnittene Substanz zeigt ebenfalls eine größere Stabilität als z. B. Phenylen- oder Äthylendiaminderivate. Ein weiterer Vorteil ist die Veränderung der beiden oder eines der beiden Benzolkerne durch Einführung von Substituenten der obengenannten Art. Durch Einführung derartiger Substituenten läßt sich eine besonders spezifische Wirkung der durch Substitution neu gewonnenen Verbindungen herausarbeiten, so daß eine starke Breitenwirkung durch Veränderung der Benzolkerne erreicht werden kann.The benzidine derivatives are already present during production of water a greater stability, so that their drying does not cope with the usual Precautions need to be taken than with other bis-dithiocarbamic acid derivatives. The dry or dry milled and blended substance also shows greater stability than z. B. phenylene or ethylene diamine derivatives. Another The advantage is that the two or one of the two benzene nuclei can be changed through introduction of substituents of the type mentioned above. By introducing such substituents can be a particularly specific effect of the newly obtained by substitution Work out connections so that a strong broad impact through change the benzene nuclei can be achieved.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB31000A DE1020481B (en) | 1954-05-13 | 1954-05-13 | Fungicidal agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB31000A DE1020481B (en) | 1954-05-13 | 1954-05-13 | Fungicidal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1020481B true DE1020481B (en) | 1957-12-05 |
Family
ID=6963374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB31000A Pending DE1020481B (en) | 1954-05-13 | 1954-05-13 | Fungicidal agent |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1020481B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134063B (en) * | 1960-09-15 | 1962-08-02 | Hoechst Ag | Process for the preparation of aryl bis-dithiocarbamates |
| JP2002114751A (en) * | 2000-08-04 | 2002-04-16 | Aventis Cropscience Sa | Fungicidal derivative of phenyl(thio)urea or phenyl(thio) carbamate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317765A (en) * | 1941-08-20 | 1943-04-27 | Rohm & Haas | Fungicidal composition |
-
1954
- 1954-05-13 DE DEB31000A patent/DE1020481B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317765A (en) * | 1941-08-20 | 1943-04-27 | Rohm & Haas | Fungicidal composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134063B (en) * | 1960-09-15 | 1962-08-02 | Hoechst Ag | Process for the preparation of aryl bis-dithiocarbamates |
| JP2002114751A (en) * | 2000-08-04 | 2002-04-16 | Aventis Cropscience Sa | Fungicidal derivative of phenyl(thio)urea or phenyl(thio) carbamate |
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