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DE1076435B - Preparations for the control of nematodes - Google Patents

Preparations for the control of nematodes

Info

Publication number
DE1076435B
DE1076435B DESCH25241A DESC025241A DE1076435B DE 1076435 B DE1076435 B DE 1076435B DE SCH25241 A DESCH25241 A DE SCH25241A DE SC025241 A DESC025241 A DE SC025241A DE 1076435 B DE1076435 B DE 1076435B
Authority
DE
Germany
Prior art keywords
days
nematodes
day
preparations
control
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
DESCH25241A
Other languages
German (de)
Inventor
Dr Horst Werres
Ernst-Albrecht Pieroh
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
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.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Priority to DESCH25241A priority Critical patent/DE1076435B/en
Publication of DE1076435B publication Critical patent/DE1076435B/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14Di-thio analogues thereof

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Mittel zur Bekämpfung von Nematoden Eine Bekämpfung der im Boden lebenden Nematoden, die besonders in letzter Zeit größere Schäden in der Landwirtschaft verursachen, ist bekanntlich schwierig, da sie gegen die meisten der bekannten Schädlingsbekämpfungsmittel resistent sind. Es wurden schon Nematocide vorgeschlagen, wie ein Gemisch von 1,3-Dichlorpropen und 1,2-Dichlorpropan, 1,2-Dibromäthan oder Dimethyldithiocarbaminsäuremethylester, jedoch ist insbesondere das letztgenannte in seiner Wirksamkeit nicht voll befriedigend.Means of controlling nematodes A control of those living in the ground Nematodes, which have caused major damage to agriculture, especially recently, is known to be difficult as it works against most of the known pesticides are resistant. Nematocides, such as a mixture of 1,3-dichloropropene, have been proposed and 1,2-dichloropropane, 1,2-dibromoethane or dimethyldithiocarbamic acid methyl ester, however, the latter in particular is not entirely satisfactory in terms of its effectiveness.

Es wurde nun gefunden, daß Verbindungen der allgemeinen Formel worin R einen Alkyl-, Aryl- oder Aralkylrest darstellt, sehr gut gegen Nematoden wirksam sind. Es kommen unter anderem Verbindungen in Frage, für die das R der obigen Formel einen Methyl-, Äthyl-, Propyl-, Phenyl- oder Benzylrest darstellt, jedoch dürfte sich diese Verbindungsklasse ganz allgemein durch eine gute nematocide Wirksamkeit auszeichnen, während z. B. die am Stickstoff disubstituierten Verbindungen nicht wirksam zu sein scheinen.It has now been found that compounds of the general formula wherein R represents an alkyl, aryl or aralkyl radical, are very effective against nematodes. There are, inter alia, compounds for which the R of the above formula represents a methyl, ethyl, propyl, phenyl or benzyl radical, but this class of compounds should generally be characterized by a good nematocidal activity, while z. B. the compounds disubstituted on nitrogen do not appear to be effective.

Die Anwendung der Verbindungen im Boden erfolgt als solche oder unter Benutzung eines inerten Verdünnungsmittels, wie Wasser, organische Flüssigkeit oder festem Trägerstoff, z. B. als Dispersion in Wasser oder Lösung in organischen Lösungsmitteln, wie z. B. Alkohol, Aceton, aromatische Kohlenwasserstoffe, wie Benzol, Xylol u. a.The application of the compounds in the ground takes place as such or under Use of an inert diluent such as water, organic liquid or solid carrier, e.g. B. as a dispersion in water or a solution in organic solvents, such as B. alcohol, acetone, aromatic hydrocarbons such as benzene, xylene and the like. a.

Die gute Wirksamkeit geht aus folgenden Versuchen hervor: A. Laborversuche In wäßrige Aufschwemmungen der nachfolgenden Substanzen wurden Larven von Aphelenchoides ritzemabosi (Schwartz), Ditylenchus dipsaci (Kühn) und Meloiddgyne sp. (Chitwood) eingebracht und nach-24 bzw. 48 Stunden die Aktivität der Tiere getestet. Die Durchführung der Versuche erfolgte bei 20' C. 10011/ö =vollständige Abtötung der Larven; 0% =nicht geschädigte Larven.The good effectiveness is evident from the following tests: A. Laboratory tests Aphelenchoides larvae were found in aqueous suspensions of the following substances ritzemabosi (Schwartz), Ditylenchus dipsaci (Kühn) and Meloiddgyne sp. (Chitwood) introduced and tested the activity of the animals after -24 or 48 hours. The implementation the experiments were carried out at 20 ° C. 10011 / ö = complete destruction of the larvae; 0% = not damaged larvae.

Cysten von Heterodera schachtii (Schmidt) wurden 48 Stünden in wäßrige Aufschwemmung der Substanzen gegeben, anschließend gewaschen und mit Rübenwurzeldiffusat zum Larvenschlüpfen angesetzt. Während beiden Kontrollschalen schon nach 3 Tagen ein starkes Larvenschlüpfen einsetzte, konnten aus den behandelten Cysten nach 40 Tagen noch keine Larven gelockt werden. Der Eiinhalt war nach Öffnen der Cysten stark granuliert und gebräunt. 1. Methylen-bis-(N-methyldithiocarbamat) ; F. = 104 bis 105' C (Zersetzung). Konzentration Aphelenchoides Ditylenchus Meloidogyne (Wirkstoff) 1 Tag 2 Tage 1 Tag 2 Tage 1 Tag 2 Tage 0,1 . . . . . . . . . . . . . . . . . . 1000/0 1001/0 1000/0 1000/0 1001/0 1000/0 0,05 . . . . . . . . . . . . . . . . 1001/0 1001/0 1001/0 10011/0 1001/0 1001/0 0,01 ................ 700/0 1000/0 - 70% 1000/0 1000/0 Heterodera schachtii: Anzahl der geschlüpften Larven: 0 nach 40 Tagen. 2. Methylen-bis-(N-äthyldithiocarbamat) ; F. = 100 bis 102' C (Zersetzung). Konzentration Aphelenchoides Ditylendius Meloidogyne (Wirkstoff) 1 Tag 2 Tage ,[ 1 Tag 2 Tage 1 Tag 2 Tage 0,1 . . . . . . . . . . . . . . . . . . 1000/0 1001/0 1000/0 10011/0 1000/0 1000/0 0,05 .... . . . . . . . . . . . . 1000/0 1000/0 1000/0 1000/0 1000/01 1000/0 0,01 . . . . . . . . . . . . . . . . 700/0 701/o - 50% 951/o 1000/0 #jeterodera schachtii: Anzahl der geschlüpften Larven: 0 nach 40 Tagen. 3. Methylen-bis-(N-benzyldithiocarbamat) ; F. = 115 bis 1160 C (Zersetzung). Konzentration Aphelenchoides Ditylenchus Meloidogyne (Wirkstoff) 1 Tag ( 2 Tage 1 Tag- 2 Tage 1 Tag 2 Tage 0,05 0,1 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1000/0 1000/0 1001/0 1000/0 30% 50110 900/0 701/9 1000/0 1000/0 1000/0 1001/0 0,01 ................ 500/0 900/0 00/0 30% 70% 800/0 B. Gewächshausversuche Die nematocide Wirkung von Methylen-bis-(N-methyldithiocarbamat) wurde im Vergleich zu 1,3-Dichlorpropen+1,2-Dichlorpropan; 1,2-Dibromäthan und Dimethyldithiocarbaminsäuremethylester im Gewächshaus über verseuchtem Boden geprüft.Cysts of Heterodera schachtii (Schmidt) were placed in an aqueous suspension of the substances for 48 hours, then washed and prepared with beet root diffusate for larvae to hatch. While both control dishes began to hatch vigorously after 3 days, no larvae could be attracted from the treated cysts after 40 days. After opening the cysts, the egg contents were heavily granulated and browned. 1. methylene bis (N-methyldithiocarbamate); F. = 104 to 105 ° C (decomposition). Concentration Aphelenchoides Ditylenchus Meloidogyne (Active ingredient) 1 day 2 days 1 day 2 days 1 day 2 days 0.1. . . . . . . . . . . . . . . . . . 1000/0 1001/0 1000/0 1000/0 1001/0 1000/0 0.05. . . . . . . . . . . . . . . . 1001/0 1001/0 1001/0 10011/0 1001/0 1001/0 0.01 ................ 700/0 1000/0 - 70% 1000/0 1000/0 Heterodera schachtii: number of hatched larvae: 0 after 40 days. 2. methylene bis (N-ethyldithiocarbamate); F. = 100 to 102 ° C (decomposition). Concentration Aphelenchoides Ditylendius Meloidogyne (Active ingredient) 1 day 2 days, [1 day 2 days 1 day 2 days 0 , 1. . . . . . . . . . . . . . . . . . 1000/0 1001/0 1000/0 10011/0 1000/0 1000/0 0.05 ..... . . . . . . . . . . . 1000/0 1000/0 1000/0 1000/0 1000/01 1000/0 0.01 . . . . . . . . . . . . . . . . 700/0 701 / o - 50% 951 / o 1000/0 #jeterodera schachtii: Number of hatched larvae: 0 after 40 days. 3. methylene bis (N-benzyldithiocarbamate); F. = 115 to 1160 C (decomposition). Concentration Aphelenchoides Ditylenchus Meloidogyne (Active ingredient) 1 day (2 days 1 day - 2 days 1 day 2 days 0.05 0.1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1000/0 1000/0 1001/0 1000/0 30% 50 110 900/0 701/9 1000/0 1000/0 1000/0 1001/0 0.01 ................ 500/0 900/0 00/0 30% 70% 800/0 B. Greenhouse Experiments The nematocidal effect of methylene bis (N-methyldithiocarbamate) was compared to 1,3-dichloropropene + 1,2-dichloropropane; 1,2-Dibromoethane and methyl dimethyldithiocarbamate were tested in the greenhouse over contaminated soil.

Methylen-bis-(N-methyldithiocarbamat) und Dimethyldithiocarbaminsäuremethylester wurden als Verreibungen gleichmäßig in die Erde gebracht, 1,3-Dichlorpropen-f-1,2-Dichlorpropan und 1,2-Dibromäthan mg Aktive Nematocide Präparat Substanz Wirkung /1 Erde 0/0 Methylen-bis-(N-methyl- 120 100 d_ithiocarbamat) 100 100 80 100 60 87 Dimethyldithiocarbamin- 120 36 säuremethylester 100 0 80 0 1,3-Dichlorpropen -1- 1,2-Di- 120 0 Chlorpropan 100 0 80 0 1,2-Dibromäthan 120 46 100 33 80 18 60 0 in die Erde injiziert, die durch Wurzelgallennema toden, Meloidogyne sp. (Chitwood) verseucht war. Nach einer Karenzzeit von 8 Tagen, bei einer Temperatur von 15' C, wurde die behandelte Erde in Tonschalen gebracht, Tomaten ausgesät und 30 Tage bei einer Bodentemperatur von 22 bis 25' C kultiviert. Danach erfolgte die Wertung der nematociden Wirkung durch Zählen der sich an den Wurzeln gebildeten Wurzelgallen.Methylene bis (N-methyldithiocarbamate) and methyl dimethyldithiocarbamate were brought into the earth as triturations, 1,3-dichloropropene-f-1,2-dichloropropane and 1,2-dibromoethane mg of active nematocides Preparation substance effect / 1 earth 0/0 Methylene-bis- (N-methyl-120 100 d_ithiocarbamate) 100 100 80 100 60 87 Dimethyldithiocarbamine- 120 36 acid methyl ester 100 0 80 0 1,3-dichloropropene -1- 1,2-di- 120 0 Chloropropane 100 0 80 0 1,2-dibromoethane 120 46 100 33 80 18 60 0 injected into the soil, killed by root knot nema, Meloidogyne sp. (Chitwood) was contaminated. After a waiting period of 8 days at a temperature of 15 ° C., the treated soil was placed in clay bowls, tomatoes were sown and cultivated for 30 days at a soil temperature of 22 to 25 ° C. The nematocidal effect was then assessed by counting the root galls formed on the roots.

Die Darstellung der Verbindungen erfolgt durch Umsetzung der entsprechenden Dithiocarbamate in alkoholischem oder wäßrigem Medium mit Methylenchlorid. Beim Arbeiten in wäßrigem Medium wird unter Rückfluß bei einer Badtemperatur von etwa 45' C gearbeitet, j edoch erfolgt auch schon bei Zimmertemperatur eine Umsetzung.The connections are represented by implementing the corresponding Dithiocarbamates in alcoholic or aqueous medium with methylene chloride. At the Working in an aqueous medium is under reflux at a bath temperature of about 45 ° C worked, but a conversion takes place even at room temperature.

Claims (1)

PATENTANSPRUCH: Mittel zur Bekämpfung von Nematoden, gekennzeichnet durch einen Gehalt an einer Verbindung der allgemeinen Formel worin R einen Alkyl-, Aryl- oder Aralkylrest darstellt.PATENT CLAIM: Agent for combating nematodes, characterized by a content of a compound of the general formula wherein R represents an alkyl, aryl or aralkyl radical.
DESCH25241A 1958-12-24 1958-12-24 Preparations for the control of nematodes Pending DE1076435B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH25241A DE1076435B (en) 1958-12-24 1958-12-24 Preparations for the control of nematodes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH25241A DE1076435B (en) 1958-12-24 1958-12-24 Preparations for the control of nematodes

Publications (1)

Publication Number Publication Date
DE1076435B true DE1076435B (en) 1960-02-25

Family

ID=7430100

Family Applications (1)

Application Number Title Priority Date Filing Date
DESCH25241A Pending DE1076435B (en) 1958-12-24 1958-12-24 Preparations for the control of nematodes

Country Status (1)

Country Link
DE (1) DE1076435B (en)

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