DE855846C - Process for the manufacture of fungicidal products - Google Patents
Process for the manufacture of fungicidal productsInfo
- Publication number
- DE855846C DE855846C DEB12510A DEB0012510A DE855846C DE 855846 C DE855846 C DE 855846C DE B12510 A DEB12510 A DE B12510A DE B0012510 A DEB0012510 A DE B0012510A DE 855846 C DE855846 C DE 855846C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- manufacture
- trichloro
- fungicidal
- dinitrobenzene
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/16—Aryl or aralkyl ethers
- C08B11/18—Aryl or aralkyl ethers with substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/14—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung fungizider Produkte Es wurde gefunden, daß man sehr wirksame fungizide Produkte erhält, wenn man I, 2, 4-Trichlor-3, 5-dinitrobenzol mit hochmolekularen Polyoxyverbindungen oder deren Äthern umsetzt.Process for the manufacture of fungicidal products It was found that very effective fungicidal products are obtained if I, 2, 4-trichloro-3, 5-dinitrobenzene are used with high molecular weight polyoxy compounds or their ethers.
Das I, 2, 4-Trichlor-3, 5-dinitrobenzol ist durch Nitrieren von 1, 2, 4-Trichlorbellzol leicht erhältlich, das seinerseits aus Hexachlorcyclohexan durch Abspaltung von Chlorwasserstoff entsteht. Geeignete hochmolekulare Polyoxyverbindungen sind z.B. The I, 2, 4-trichloro-3, 5-dinitrobenzene is by nitrating 1, 2,4-Trichlorobellzene easily available, which in turn is made from hexachlorocyclohexane by splitting off hydrogen chloride. Suitable high molecular weight polyoxy compounds are e.g.
Polysaccharide, wie Cellulose, und deren Methyl-, Oxyäthyl- oder Glykolsäureäther, ferner sogenannte Holzäthercarbonsäure (d. h. Umsetzungsprodukte von Holz mit Chloressigsäure) sowie Stärke, Pektinstoffe, Inulin oder Polyvinylalkohol.Polysaccharides, such as cellulose, and their methyl, oxyethyl or glycolic acid ethers, also so-called wood ether carboxylic acid (i.e. reaction products of wood with chloroacetic acid) as well as starch, pectins, inulin or polyvinyl alcohol.
Die Umsetzung erfolgt durch Vermischen oder Verkneten der Komponenten, gewünschtenfalls in Gegenwart von Lösungs- oder Verdünnungsmitteln wie Wasser oder Methanol. Um den entstehenden Chlorwasserstoff zu binden, ist die Mitverwendung säurehindender Mittel, wie Alkalilauge, förderlich. The implementation takes place by mixing or kneading the components, if desired in the presence of solvents or diluents such as water or Methanol. In order to bind the resulting hydrogen chloride, it is also used acid-inhibiting agents, such as alkali, are beneficial.
Zweckmäßig wendet man z. 13. die Cellulose in Form von Alkalicellulose und die carhoxylgruppenhaltigen Äther in Form ihrer Alkalisalze an. Die Umsetzung verläuft im allgemeinen bei Verwendung von I Mol I, 2, 4-Trichlor-3, 5-dinitrobenzol je Saccharid-Einheit bereits bei gewöhnlicher Temperatur im Laufe mehrerer Stunden vollständig; zu-Teilen ist Erhitzen his auf etwa 2000 förderlich. Appropriately, one uses z. 13. Cellulose in the form of alkali cellulose and the ethers containing caroxyl groups in the form of their alkali salts. The implementation generally proceeds when using 1 mole of 1,2,4-trichloro-3,5-dinitrobenzene per saccharide unit even at normal temperature over the course of several hours Completely; Heating up to about 2000 is conducive to dividing.
Man kann auch größere oder kleinere stöchiometrische Verhältnisse anwenden.You can also use larger or smaller stoichiometric ratios use.
Die erhaltenen Reaktionsprodukte sind in Wasser leicht verteilhar und zeigen auch in starker Verdünnung noch eine erheblich größere fungizide Wirkung als das 1,2, -Trichlor-3, s-dinitrol)enzol selbst, ohne wie dieses Blattschädigung zu verursachen. Daß die Kombination des schwach fungiziden I, 2, 4-Trichlor-3, 5-dinitrobenzols mit hochmolekularen Polyoxyverbindungen eine so außerordentliche Steigerung der fungiziden Wirkung hervorruft, ist überraschend; die gleichfalls nur schwache fungizideWirkung desMononitro- 1 ,2,4-trichlorbenzols wird nämlich bei der Kombination mit hochmolekularen Polyoxyverbindungen, wie gleichfalls gefunden wurde, verringert. The reaction products obtained are easily distributed in water and show a considerably greater fungicidal effect even when strongly diluted than 1,2-trichloro-3, s-dinitrol) enzol itself, without leaf damage like this to cause. That the combination of the weakly fungicidal 1,2,4-trichloro-3,5-dinitrobenzene with high molecular weight polyoxy compounds such an extraordinary increase in causes fungicidal effect is surprising; the also only weak fungicidal effect desMononitro- 1, 2,4-trichlorobenzene is used in combination with high molecular weight Polyoxy compounds, as was also found, decreased.
Die in den Beispielen genannten Teile sind Gewichtsteile. The parts mentioned in the examples are parts by weight.
Beispiel I 240 Teile Holzäthercarbonsäure, hergestellt nach Patent 712666, werden in einem Kneter mit einer Lösung von 40 Teilen Ätznatron in 40 Teilen Wasser bei gewöhnlicher Temperatur 2 Stunden gut durchgearl>eitet. Dann fügt man allmählich 272 Teile fein gepulvertes I, 2, 4-Trichlor-3, 5-dinitrobenzol hinzu und knetet 4 Stunden weiter. Das erhaltene Produkt verhindert das Wachstum von Aspergillus-niger-Kulturen auf Agar-Agar in einer Verdünnung von I:30000 völlig; bei I:rooooo ist noch eine starke Wachstumshemmung zu beol)achten. Example I 240 parts of wood ether carboxylic acid, prepared according to the patent 712666, are in a kneader with a solution of 40 parts of caustic soda in 40 parts Water permeates well for 2 hours at normal temperature. Then adds gradually adding 272 parts of finely powdered 1,2,4-trichloro-3,5-dinitrobenzene and knead for 4 hours. The product obtained prevents the growth of Aspergillus niger cultures on agar-agar at a dilution of I: 30000 completely; at I: rooooo is another one strong growth inhibition to be observed.
Beispiel 2 Man trägt bei gewöhnlicher Temperatur unter Rühren in eine Lösung von IooTeilen 1. 2, 4-Trichlor-3, s-dinitrol)enzol in 350 Teilen Methanol loo Teile Alkalicellulose ein. Dann wird das Gemisch auf etwa I00° erhitzt, bis das Methanol verdampft ist. Der Rückstand wird in einer Kugelmühle fein gemahlen. Das erhaltene Produkt zeigt ähnliche Wirkungen wie das gemäß Beispiel I erhaltene. Example 2 One carries in at ordinary temperature with stirring a solution of 100 parts of 1,2,4-trichloro-3, s-dinitrol) enzene in 350 parts of methanol loo parts of alkali cellulose. Then the mixture is heated to about 100 ° until the methanol has evaporated. The residue is finely ground in a ball mill. The product obtained shows effects similar to that obtained in Example I.
Beispiel 3 Man verarl>eitet in einem Kneter bei gewöhnlicher Temperatur 110 Teile der im beispiel 1 genannten Holzäthercarbonsäure mit [o Teilen Wasser und 55 Teilen I, 2, 4-Trichlor-3, s-dinitrobenzol und zerkleinert das nach l/2stündigem Kneten erhaltene Produkt durch 3stündiges Mahlen in einer Kugelmühle. Die Wirkung ist ähnlich der des nach Beispiel 1 erhältlichen Produkts. Example 3 Processing is carried out in a kneader at ordinary temperature 110 parts of the wood ether carboxylic acid mentioned in Example 1 with [o parts of water and 55 parts of I, 2, 4-trichloro-3, s-dinitrobenzene and crushed after 1/2 hour Knead the product obtained by milling for 3 hours in a ball mill. The effect is similar to that of the product obtainable according to Example 1.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB12510A DE855846C (en) | 1950-11-15 | 1950-11-15 | Process for the manufacture of fungicidal products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB12510A DE855846C (en) | 1950-11-15 | 1950-11-15 | Process for the manufacture of fungicidal products |
Publications (1)
Publication Number | Publication Date |
---|---|
DE855846C true DE855846C (en) | 1952-11-17 |
Family
ID=6957158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB12510A Expired DE855846C (en) | 1950-11-15 | 1950-11-15 | Process for the manufacture of fungicidal products |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE855846C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230634B (en) * | 1963-02-28 | 1966-12-15 | Siemens Ag | Valve for vacuum systems, especially for corpuscular beam devices |
-
1950
- 1950-11-15 DE DEB12510A patent/DE855846C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230634B (en) * | 1963-02-28 | 1966-12-15 | Siemens Ag | Valve for vacuum systems, especially for corpuscular beam devices |
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