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DE1075372B - Pesticides with fungicidal properties - Google Patents

Pesticides with fungicidal properties

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Publication number
DE1075372B
DE1075372B DENDAT1075372D DE1075372DA DE1075372B DE 1075372 B DE1075372 B DE 1075372B DE NDAT1075372 D DENDAT1075372 D DE NDAT1075372D DE 1075372D A DE1075372D A DE 1075372DA DE 1075372 B DE1075372 B DE 1075372B
Authority
DE
Germany
Prior art keywords
isothiourea
pesticides
hcl
ether
fungicidal
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
Application number
DENDAT1075372D
Other languages
German (de)
Inventor
Wiesbaden Dr. Alfred Englisch Eltville Dr. Rolf Zimmermann (Rheingau) und Dr. Ernst August Bartels, Wiesbaden
Original Assignee
Chemische Werke Albert, Wiesbaden-Biebrich
Priority date (The priority date 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 date listed.)
Publication date
Publication of DE1075372B publication Critical patent/DE1075372B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

DEUTSCHESGERMAN

INTERNAT.INTERNAT.

kl. AOInkl. AOIn

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFT 1075 372EXPLAINING EDITORIAL 1075 372

C 17219 IVa/451C 17219 IVa / 451

ANMELDETAG: 25.JULI1958REGISTRATION DATE: JULY 25, 1958

B EKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AÜSLEGESCHRIFT: 11. FEBRUAR 1960NOTICE
THE REGISTRATION
AND ISSUE OF THE
LEGEND: FEBRUARY 11, 1960

Es wurde gefunden, daß Isothioharnstoff-methylalkyläther-hydrochloride der allgemeinen FormelIt has been found that isothiourea methyl alkyl ether hydrochloride the general formula

R-O-CH9 RO-CH 9

NHNH

NH9 NH 9

HClHCl

in der R einen aliphatischen Rest von CH3 bis C18H37 bedeutet, Verbindungen mit sehr guter fungizider Wirksamkeit darstellen. Man erhält diese Körper nach einem älteren Verfahren in nahezu quantitativer Ausbeute, indem man Alkylchlormethyläther in Lösung, z. B. in acetonischer Lösung, mit Thioharnstoff zur Reaktion bringt. Die fungizide Wirksamkeit dieser Isothioharnstoffmethylalkyläther-hydrochloride ist abhängig von der Anzahl der C-Atome im Alkylrest und nimmt mit steigender Kettenlänge zu.in which R denotes an aliphatic radical from CH 3 to C 18 H 37 , represent compounds with very good fungicidal activity. This body is obtained by an older process in almost quantitative yield by adding alkyl chloromethyl ether in solution, e.g. B. in acetone solution, reacts with thiourea. The fungicidal effectiveness of these isothiourea methyl alkyl ether hydrochlorides depends on the number of carbon atoms in the alkyl radical and increases with increasing chain length.

Folgende Tabelle bringt eine Zusammenstellung der Prüfungsergebnisse gegen Alternaria tenuis:The following table summarizes the test results against Alternaria tenuis:

Schädlingsbekämpfungsmittel mit fungizider WirkungPesticides with fungicidal properties

Anmelder:Applicant:

Chemische Werke Albert, Wiesbaden-Biebrich, Albertstr. 10-14Chemical works Albert, Wiesbaden-Biebrich, Albertstr. 10-14

Dr. Rolf Zimmermann, Wiesbaden,Dr. Rolf Zimmermann, Wiesbaden,

Dr. Alfred Englisch, Eltville (Rheingau),Dr. Alfred English, Eltville (Rheingau),

und Dr. Ernst August Bartels, Wiesbaden, sind als Erfinder genannt wordenand Dr. Ernst August Bartels, Wiesbaden, have been named as the inventor

Verbindunglink NH2 NH 2 ?? NH2 NH 2 •• NH2 NH 2 HClHCl Wirkstoffmenge / qcm
DL100 / 24 Stunden
BeobachtungsdauerAmount of active ingredient / qcm
DL 100/24 hrs
Observation period 1.1. Isothioharnstoff-methyhnethylather-hydrochloridIsothiourea methyl ether hydrochloride NHNH NHNH NHNH
ΛΛ 79 bis 80 γ 79 to 80 γ VV
•• 2.2. NH
CH3-O-CH2-S-C^NH
CH 3 -O-CH 2 -SC ^ NH2 NH 2 HClHCl Isothioharnstoff-methylbutyläther-hydrochloridIsothiourea methyl butyl ether hydrochloride 80 bis 90 γ 80 to 90 γ 3.3. CH3 — (CH2)3 — 0 — CH2 — S — C ( CH 3 - (CH 2 ) 3 - 0 - CH 2 - S - C ( HClHCl Isothioharnstoff-methylamyläther-hydrochloridIsothiourea methyl amyl ether hydrochloride 40 γ 40 γ 4.4th CH3 — (CH2), — 0 — CH2- S — C ( CH 3 - (CH 2 ), - 0 - CH 2 - S - C ( HClHCl Isothioharnstoff-methyloctyläther-hydrochloridIsothiourea methyl octyl ether hydrochloride 2Oy2Oy CH3- (CH2)7 — 0 — CH2-S — C^CH 3 - (CH 2 ) 7-0 -CH 2 -S-C ^

1 U/t) ό /2 1 U / t) ό / 2

33 Verbindunglink NHNH CH3 — (CH2)9 — 0 — CH2 — S — C fCH 3 - (CH 2 ) 9-0 - CH 2 - S - C f NH2 NH 2 6. Isothioharnstoff-methyllauryläther-hydrochlorid6. Isothiourea methyl lauryl ether hydrochloride NHNH CH3 — (CH2)U — O — CH2 — S — C 'f CH 3 - (CH 2 ) U - O - CH 2 - S - C 'f NH2 NH 2 8. Isothioharnstoff-methylcetyläther-hydrochlorid8. Isothiourea methylcetyl ether hydrochloride NHNH 9. Mischung von C12-, C14- und C16-Derivaten9. Mixture of C 12 , C 14 and C 16 derivatives HClHCl 44th 5. Isothioharnstoff-methyldecyläther-hydrochlorid5. Isothiourea methyl decyl ether hydrochloride 7. Isothioharnstoff-methylmyristyläther-hydrochlorid7. Isothiourea methyl myristyl ether hydrochloride CH3 — (CH2J15 — 0 — CH2 — S — C^CH 3 - (CH 2 J 15 - 0 - CH 2 - S - C ^ 10. Isothioharnstoff-methyl-2-äthylhexyläther-hydrochlorid10. Isothiourea methyl 2-ethylhexyl ether hydrochloride Wirkstoffmenge / qcm
DL100 / 24 Stunden
BeobachtungsdauerAmount of active ingredient / qcm
DL 100/24 hrs
Observation period ^NH^ NH NH2 NH 2 NH
CH3-(CH2)3 — CH-CH2- 0— CH2-S-C^NH
CH 3 - (CH 2 ) 3 - CH-CH 2 - 0 - CH 2 -SC ^ OXI3 (OXI2J13 ^ ^J^-2 ^ \ *OXI3 (OXI2J13 ^ ^ J ^ -2 ^ \ * NH2 NH 2 HClHCl 2Oy2Oy HClHCl 1Oy1Oy HClHCl unter 10 yunder 10 y HClHCl 2Oy2Oy 1Oy1Oy 1Oy1Oy

Die Wirksamkeit der neuen Wirkstoffe ist beispielsweise auch gegenüber Rebenperonospora (Plasmopara viticola) und gegenüber Kartoffelkrautfäule (phytophthora infestans) vorhanden. Ihre Pflanzenverträglichkeit ist gut, ihre Töxizität gegenüber Warmblütern gering.The effectiveness of the new active ingredients is, for example, also against vine peronospora (Plasmopara viticola) and against potato leaf blight (phytophthora infestans) present. Your plant tolerance is good, its toxicity towards warm-blooded animals is low.

Zur Herstellung von fungiziden Präparaten können die Wirkstoffe mit Netz- oder Emulgiermitteln, Füllstoffen, Trägerstoffen, Lösungsmitteln u. dgl. versehen werden. Sie können als Stäubemittel, Spritzmittelpulver und Emulsionen zur Anwendung kommen. Darüber hinaus sind Kombinationen mit anderen bekannten Fungiziden möglich.For the production of fungicidal preparations, the active ingredients can be mixed with wetting or emulsifying agents, fillers, Carriers, solvents and the like are provided. They can be used as a dusting agent, spray powder and Emulsions are used. In addition, there are combinations with other known fungicides possible.

In der Literatur werden S-acylierte sowie alkylierte Isothioharnstoffe beschrieben, die als Schädlingsbekämp-: fungsmittel dienen. Im Gegensatz dazu handelt es sich bei den Produkten gemäß vorliegender Erfindung um Methylalkyl Äther-Derivate des Isothioharnstoffes, also um eine andere Gruppe von Verbindungen.In the literature S-acylated be described and alkylated isothiourea, as pest: fung medium used. In contrast to this, the products according to the present invention are methylalkyl ether derivatives of isothiourea, that is to say another group of compounds.

Ausgangsprodukte sind für die bekannten Verbindungen Alkylhalogenide, die mit Thioharnstoff erst nach mehrstündigem Kochen die Alkylderivate in wenig reiner Form und in Ausbeuten von maximal nur 60 % liefern. Die vorliegende Erfindung dagegen geht von Chlormethyläthern aus, die mit Isothioharnstoff schon bei Raumtemperatur die entsprechenden Isothioharnstoff-Äther-Derivate in quantitativer Ausbeute und großer Reinheit ergeben. Die zur Herstellung der Äther verwendeten Alkohole sind billig und leicht zugänglich, was für die Alkylhalogenide nicht zutrifft. Die Ätherbildung selbst verläuft ebenfalls glatt und einfach.The starting materials for the known compounds are alkyl halides, those with thiourea only after several hours Cooking gives the alkyl derivatives in a poorly pure form and in yields of a maximum of only 60%. The present invention, however, is based on chloromethyl ethers, which with isothiourea already at room temperature the corresponding isothiourea ether derivatives in quantitative yield and high purity result. The alcohols used to make the ethers are cheap and readily available, which is what the Alkyl halides does not apply. The ether formation itself is also smooth and simple.

Vergleichsversuche an jungen Bohnen- und Senfpflanzen zeigten außerdem eine wesentlich geringere Phytotoxizität der erfindungsgemäßen Produkte.Comparative tests on young bean and mustard plants also showed a significantly lower rate Phytotoxicity of the products according to the invention.

Claims (2)

Patentansprüche·.Claims ·. 1. Schädlingsbekämpfungsmittel mit fungizider Wirkung, daduich gekennzeichnet, daß sie als wirksame Substanzen Isothioharnstoff-methylalkylätherhydrochloride der allgemeinen Formel1. Pesticides with fungicidal action, characterized in that they are active substances isothiourea-methylalkylether hydrochloride of the general formula NHNH R_O —CH2-S —C;R_O —CH 2 —S — C; HClHCl NH,NH, enthalten, in der R einen aliphatischen Rest von CH3 bis C18H37 bedeutet.in which R is an aliphatic radical from CH 3 to C 18 H 37 . 2. Schädlingsbekämpfungsmittel gemäß Anspruch 1, dadurch gekennzeichnet, daß sie die Wirkstoffe in Kombination mit Netzmitteln, Emulgiermitteln, Füllstoffen, Trägerstoffen, Lösungsmitteln und/oder mit anderen bekannten fungiziden Mitteln enthalten.2. Pesticides according to claim 1, characterized in that they contain the active ingredients Combination with wetting agents, emulsifiers, fillers, carriers, solvents and / or with contain other known fungicidal agents. In Betracht gezogene Druckschriften:
Deutsche Patentschriften Nr. 940 554, 947 209.Considered publications:
German patent specifications No. 940 554, 947 209. © 909 729/418 2.60© 909 729/418 2.60
DENDAT1075372D 1958-07-08 Pesticides with fungicidal properties Pending DE1075372B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEC0017144 1958-07-08
DEC0017249 1958-07-25

Publications (1)

Publication Number Publication Date
DE1075372B true DE1075372B (en) 1960-02-11

Family

ID=25969214

Family Applications (1)

Application Number Title Priority Date Filing Date
DENDAT1075372D Pending DE1075372B (en) 1958-07-08 Pesticides with fungicidal properties

Country Status (3)

Country Link
CH (1) CH374982A (en)
DE (1) DE1075372B (en)
GB (1) GB886325A (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE940554C (en) * 1952-01-08 1956-03-22 Bataafsche Petroleum Treatment of plants for the purpose of combating pathogens
DE947209C (en) * 1952-09-21 1956-08-09 Bataafsche Petroleum Treatment of plants to combat pathogens, particularly fungi

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE940554C (en) * 1952-01-08 1956-03-22 Bataafsche Petroleum Treatment of plants for the purpose of combating pathogens
DE947209C (en) * 1952-09-21 1956-08-09 Bataafsche Petroleum Treatment of plants to combat pathogens, particularly fungi

Also Published As

Publication number Publication date
CH374982A (en) 1964-02-15
GB886325A (en) 1962-01-03

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