DE1024745B - Gastropod antipoders - Google Patents

Gastropod antipoders

Info

Publication number
DE1024745B
DE1024745B DEF18509A DEF0018509A DE1024745B DE 1024745 B DE1024745 B DE 1024745B DE F18509 A DEF18509 A DE F18509A DE F0018509 A DEF0018509 A DE F0018509A DE 1024745 B DE1024745 B DE 1024745B
Authority
DE
Germany
Prior art keywords
trichloro
nitrosalicylanilide
gastropod
nitro
acetoxybenzanilide
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
DEF18509A
Other languages
German (de)
Inventor
Dr Ernst Schraufstaetter
Dr Rudolf Goennert
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 AG
Original Assignee
Bayer 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
Priority to BE551294D priority Critical patent/BE551294A/xx
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF18509A priority patent/DE1024745B/en
Priority to CH352868D priority patent/CH352868A/en
Publication of DE1024745B publication Critical patent/DE1024745B/en
Pending legal-status Critical Current

Links

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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/48—Nitro-carboxylic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Description

Gastropoden-Bekämpfungsmittel Schnecken sind nicht nur landwirtschaftliche Schädlinge, ihnen kommt auch große Bedeutung als Zwischenwirte für menschliche und tierische Infektionen zu. Die Saugwürmer (Trematoden) machen z. B. in der Schnecke eine Entwicklung durch, in deren Verlauf es zu einer ungeschlechtlichen Vermehrung der Larvenstadien kommt. Der Entwicklungszyklus der Saugwürmer der Gattung Schistosoma, welche die Bilharzioseerkrankung des Menschen hervorrufen, verläuft auch über Schnecken als Zwischenwirte. Die Wurmeier der Schistosoma werden mit den Fäkalien ausgeschieden. Sie enthalten schon eine vollentwickelte Larve (Miracidium), die im Wasser aus dem Ei schlüpft und in Schnecken eindringt. In diesen entwickeln sich aus dem Miracidium bis zu 40000 Cercarien, die aus der Schnecke auswandern und befähigt sind, die intakte menschliche Haut zu durchbohren. Im Menschen wachsen die Parasiten dann zur Geschlechtsreife heran.Gastropod Controls Snails are not just agricultural Pests, they are also of great importance as intermediate hosts for human and animal infections too. The flukes (trematodes) make z. B. in the snail a development in the course of which there is asexual reproduction the larval stage comes. The development cycle of the flukes of the genus Schistosoma, which cause schistosomiasis disease in humans also runs through snails as intermediate hosts. The worm eggs of the Schistosoma are excreted with the faeces. They already contain a fully developed larva (Miracidium) that emerges from the water in the water Egg hatches and enters snails. In these develop from the Miracidium up to 40,000 cercariae that migrate from the snail and are capable of keeping the intact pierce human skin. In humans, the parasites then grow to sexual maturity approach.

Für eine Bekämpfung der Trematodenerkrankungen ist demnach nicht nur eine medikamentöse Behandlung der infizierten Menschen oder Tiere wichtig, sondern ebenso die Vernichtung der als Zwischenwirte dienenden Schnecken, damit eine Unterbrechung des Entwicklungszyklus der Parasiten eintritt. Für epidemiologische Bekämpfungsmaßnahmen scheint der zweite Weg sogar der erfolgversprechendere zu sein, da es mit Hilfe der Chemotherapeutika bisher nicht gelungen ist, die Zahl der Bilharziosekranken wesentlich zu vermindern.For a fight against the trematode diseases is therefore not only drug treatment of infected humans or animals is important, rather likewise the destruction of the snails serving as intermediate hosts, thus an interruption the development cycle of the parasite occurs. For epidemiological control measures the second way seems to be even more promising, since it is with help The chemotherapeutic agents so far have not succeeded in reducing the number of schistosomiasis sufferers to decrease significantly.

Als Schneckenbekämpfungsmittel wird nun seit langem Kupfersulfat verwendet. Neuerdings wird weiter Pentachlorphenol als Molluscicid empfohlen und vor einiger Zeit wurde auch die schneckenabtötende Wirkung des 5,5'-Dibromsalicils bekannt. Die Spezifität der genannten Verbindungen ist jedoch noch relativ gering. So zeigen die bisher untersuchten Substanzen bestenfalls eine Wirkung bis zur Verdünnung von 10-5 bis 10-5#5.Copper sulfate has long been used as a snail control agent. Recently, pentachlorophenol has continued to be recommended as a molluscicide, and more than a few The snail-killing effect of 5,5'-dibromosalicil also became known. However, the specificity of the compounds mentioned is still relatively low. So show the substances investigated so far have at best an effect up to a dilution of 10-5 to 10-5 # 5.

Es wurde nun gefunden, daß gewisse 2-Oxybenzanilide bzw. deren 0-Acylderivate wirksame Schneckenbekämpfungsmittel darstellen, die noch in Konzentrationen bis 10-'Schnecken abzutöten vermögen. Besonders wirksam sind diejenigen 2-Oxybenzanilidderivate, die mit mindestens 2 Halogenatomen oder mit mindestens 1 Halogenatom und einer Nitrogruppe substituiert sind. Es können jedoch auch zusätzliche Substituenten, wie z. B. Alkyl-oder Alkoxygruppen, im Molekül vorhanden sein. Geeignete Verbindungen sind z. B.: 5-Chlor-4'-nitrosalicylanilid (Schmp. 260°) 5,2'-Dichlor-4'-nitrosalicylanilid (Schmp. 233') 5-Nitro-4'-chlorsalicylanilid (Schmp. 252°) 3,5,4'-Trichlorsalicylanilid (Schmp. 192°) 5,3',5'-Trichlor-2'-nitrosalicylanilid (Schmp. 190°) 5,2',5'-Trichlor-4'-nitrosalicylanilid (Schmp. 218°) 5,2'-Dichlor-5'-trifluormethylsalicylanilid (Schmp. 179'') 5,2', 5'-Trichlor-3-methyl-4'-nitrosalicylanilid (Schmp. 194°) 5,5'-Dichlor-2'-methyl-4'-nitrosalicylanilid (Schmp. 235') 5,3'-Dichlor-4'-nitrosalicylanilid (Schmp. 241') 5,2',5'-Trichlor-3,4'-dinitrosalicylanilid (Schmp. 199°) 5,2',3',6'-Tetrachlor-4'-nitrosalicylanilid (Schmp. 195°) 5,4',6'-Trichlor-2'-nitrosalicylanilid (Schmp. 204°) 5-Brom-2',5'-dichlor-4'-nitrosalicylanilid (Schmp. 234°) 5,2',4'-Trichlor-2-acetoxybenzanilid (Schmp. 157") 5,3',5'-Trichlor-2-acetoxybenzanilid (Schmp. 138°) 5,3',5'-Trichlor-2-chloracetoxybenzanilid (Schmp. 149") 5,2',5'-Trichlor-4'-nitro-2-acetoxvbenzanilid (Schmp. 169°) 5,4'-Dichlor-3'-nitro-2-acetoxybenzanilid (Schmp. 172°) 5,2',5'-Trichlor-3-methy 1-4'-nitro-2-acetoxybenzanilid (Schmp. 165') 5,2',5'-Trichlor-2-acetoxybenzanilid (Schmp. 145°) 5,2',6'-Trichlor-4'-nitrosalicylanilid (Schmp. 230°) 3,5,2',5'-Tetrachlor-4'-nitrosalicylanilid (Schmp. 226°) 5,4'-Dichlor-3-jod-salicylanilid (Schmp. 185') 5,4'-Dichlor-2'-nitro-salicylanilid (Schmp. 175°) Die Herstellung dieser erfindungsgemäß verwendbaren Verbindungen erfolgt nach bekannten Methoden aus den entsprechenden 2-Oxybenzoesäuren und deren funktionellen Derivaten und den entsprechenden Anilinderivaten. Es können aber auch in 2-Oxybenzanilid und seinen Derivaten nachträglich die wirkungsverstärkenden Halogenatome und/oder Nitrogruppen eingeführt werden.It has now been found that certain 2-oxybenzanilides or their 0-acyl derivatives are effective snail control agents that are still available in concentrations of up to Able to kill 10 'snails. Those 2-oxybenzanilide derivatives are particularly effective, those with at least 2 halogen atoms or with at least 1 halogen atom and one nitro group are substituted. However, additional substituents, such as. B. alkyl or Alkoxy groups, be present in the molecule. Suitable compounds are e.g. E.g .: 5-chloro-4'-nitrosalicylanilide (Mp. 260 °) 5,2'-dichloro-4'-nitrosalicylanilide (mp. 233 ') 5-nitro-4'-chlorosalicylanilide (M.p. 252 °) 3,5,4'-trichlorosalicylanilide (m.p. 192 °) 5,3 ', 5'-trichloro-2'-nitrosalicylanilide (Mp. 190 °) 5,2 ', 5'-trichloro-4'-nitrosalicylanilide (mp. 218 °) 5,2'-dichloro-5'-trifluoromethylsalicylanilide (M.p. 179 ") 5,2 ', 5'-trichloro-3-methyl-4'-nitrosalicylanilide (mp. 194 °) 5,5'-dichloro-2'-methyl-4'-nitrosalicylanilide (M.p. 235 ') 5,3'-dichloro-4'-nitrosalicylanilide (m.p. 241') 5,2 ', 5'-trichloro-3,4'-dinitrosalicylanilide (Mp. 199 °) 5,2 ', 3', 6'-tetrachloro-4'-nitrosalicylanilide (mp. 195 °) 5,4 ', 6'-trichloro-2'-nitrosalicylanilide (M.p. 204 °) 5-bromo-2 ', 5'-dichloro-4'-nitrosalicylanilide (m.p. 234 °) 5,2', 4'-trichloro-2-acetoxybenzanilide (M.p. 157 ") 5,3 ', 5'-trichloro-2-acetoxybenzanilide (mp. 138 °) 5,3', 5'-trichloro-2-chloroacetoxybenzanilide (Mp. 149 ") 5,2 ', 5'-trichloro-4'-nitro-2-acetoxybenzanilide (mp. 169 °) 5,4'-dichloro-3'-nitro-2-acetoxybenzanilide (Mp. 172 °) 5,2 ', 5'-trichloro-3-methy 1-4'-nitro-2-acetoxybenzanilide (mp. 165') 5,2 ', 5'-trichloro-2-acetoxybenzanilide (mp. 145 °) 5,2', 6'-trichloro-4'-nitrosalicylanilide (Mp. 230 °) 3,5,2 ', 5'-tetrachloro-4'-nitrosalicylanilide (mp. 226 °) 5,4'-dichloro-3-iodo-salicylanilide (Mp. 185 ') 5,4'-dichloro-2'-nitro-salicylanilide (mp. 175 °) The production these compounds which can be used according to the invention are carried out by known methods from the corresponding 2-oxybenzoic acids and their functional derivatives and the corresponding aniline derivatives. But it can also be in 2-oxybenzanilide and its Derivatives subsequently add the effect-enhancing halogen atoms and / or nitro groups to be introduced.

Die wirksamen Verbindungen können allein oder als Gemisch von zwei oder mehreren solcher Verbindungen angewandt werden. Sie können als solche oder nach Verarbeitung mit einem geeigneten Träger, wobei gegebenenfalls noch ein anderes molluscicides Mittel zugesetzt werden kann, angewendet werden. Geeignete Träger für staubförmige Zubereitungen sind z. B. Fullererde, Bentonit, Talkum, Holzmehl usw. Diesen pulverförmigen Produkten können auch noch Netzmittel zugesetzt werden. Flüssige Zubereitungen erhält man, wenn man die Wirkstoffe mit einem Emulgator und Wasser und oder einem organischen Lösungsmittel verarbeitet. Die 2-Oxybenzanilidderivate können auch in Form ihrer Alkalisalze Verwendung finden.The active compounds can be used alone or as a mixture of two or more such compounds are used. You can as such or after processing with a suitable carrier, optionally with another molluscicides agent can be added, can be applied. Suitable carriers for powdery preparations are z. B. Fuller's earth, Bentonite, Talc, wood flour, etc. These powdery products can also contain wetting agents can be added. Liquid preparations are obtained by using the active ingredients an emulsifier and water and / or an organic solvent. The 2-oxybenzanilide derivatives can also be used in the form of their alkali salts.

Beispiel 1 Je zehn Schnecken (Australorbis guadelupensis) werden in Bechergläsern verschiedenen Konzentrationen der zu untersuchenden Substanzen ausgesetzt und hierbei diejenige Konzentration ermittelt, bei der nach 24stündiger Einwirkung sämtliche Schnecken abgetötet werden. Die Ergebnisse dieser Prüfung sind in folgender Tabelle zusammengestellt Geprüfte Verbindung Wirksame Konzentration Pentachlorphenol . . . . . . . . . . . . . . . . . . 10-5 5,5'-Dibromsalicyl . . . . . . . . . . . . . . . . . 10-5 5,2',5'-Trichlor-4'-nitrosalicylanilid ... 10 6.5 5,2',5'-Trichlor-3-methyl-4'-nitro- 2-acetoxybenzanilid .............. 10-6,5 Beispiel 2 50 g feingemahlenes 5,2',5'-Trichlor--l'-nitrosalicylanilid mit einer Teilchengröße von 5 Mikron oder kleiner werden mit 50 g Talkum gut vermischt und diese Mischung zur Bekämpfung von Gastropoden verwendet.EXAMPLE 1 Ten snails (Australorbis guadelupensis) are exposed to different concentrations of the substances to be examined in beakers and the concentration at which all snails are killed after 24 hours of exposure is determined. The results of this test are summarized in the following table Tested connection effective concentration Pentachlorophenol. . . . . . . . . . . . . . . . . . 10-5 5,5'-dibromosalicylic. . . . . . . . . . . . . . . . . 10-5 5,2 ', 5'-trichloro-4'-nitrosalicylanilide ... 10 6.5 5,2 ', 5'-trichloro-3-methyl-4'-nitro- 2-acetoxybenzanilide .............. 10-6.5 Example 2 50 g of finely ground 5,2 ', 5'-trichloro-l'-nitrosalicylanilide with a particle size of 5 microns or smaller are mixed well with 50 g of talc and this mixture is used to control gastropods.

Beispiel 3 15 g feingemahlenes 5,2',5'-Trichlor-3-methyl--1'-nitro-2'-acetoxybenzanilid werden mit 80 g Glykolmonobutyläther und 5 g eines Polyglykolphenylätheremulgators zu einer Suspension verarbeitet und diese Suspension zur Schneckenbekämpfung verwendet.Example 3 15 g of finely ground 5,2 ', 5'-trichloro-3-methyl-1'-nitro-2'-acetoxybenzanilide are with 80 g of glycol monobutyl ether and 5 g of a polyglycol phenyl ether emulsifier processed into a suspension and this suspension used to control snails.

Claims (3)

PATENTANSPRC CfiE: 1. Gastropoden-Bekämpfungsmittel, enthaltend 2-Oxybenzanilide bzw. deren O Acylderivate, die mit mindestens 2 Kernhalogenatomen oder mit mindestens einer Nitrogruppe und mindestens 1 Halogenatom neben gegebenenfalls weiteren Substituenten substituiert sind. PATENT APPLICATION: 1. Gastropod control agents containing 2-oxybenzanilides or their O acyl derivatives with at least 2 nuclear halogen atoms or with at least a nitro group and at least 1 halogen atom in addition to optionally further substituents are substituted. 2. Gastropoden-Bekämpfungsmittel nach Anspruch 1, dadurch gekennzeichnet, daß es den Wirkstoff in Staubform, mit einem staubförmigen Träger gemischt, enthält. 2. gastropod control agent according to claim 1, characterized in that that it contains the active ingredient in the form of a powder mixed with a carrier in the form of a powder. 3. Gastropoden-Bekämpfungsmittel nach Anspruch 1, dadurch gekennzeichnet, daß es den Wirkstoff in suspendierter Form enthält.3. gastropod control agent according to claim 1, characterized in that it contains the active ingredient in suspended form.
DEF18509A 1955-09-26 1955-09-26 Gastropod antipoders Pending DE1024745B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE551294D BE551294A (en) 1955-09-26
DEF18509A DE1024745B (en) 1955-09-26 1955-09-26 Gastropod antipoders
CH352868D CH352868A (en) 1955-09-26 1956-08-25 Use of oxybenzyl anilides or their O-acyl derivatives or salts as gastropod control agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18509A DE1024745B (en) 1955-09-26 1955-09-26 Gastropod antipoders

Publications (1)

Publication Number Publication Date
DE1024745B true DE1024745B (en) 1958-02-20

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ID=7088978

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF18509A Pending DE1024745B (en) 1955-09-26 1955-09-26 Gastropod antipoders

Country Status (3)

Country Link
BE (1) BE551294A (en)
CH (1) CH352868A (en)
DE (1) DE1024745B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1126374B (en) * 1959-08-27 1962-03-29 Bayer Ag Process for the preparation of alkanolamine salts of salicylanilides
US3074848A (en) * 1960-02-02 1963-01-22 Bayer Ag 2-hydroxy-5,2'-dichloro-4'-nitrobenzanilide for combating tapeworms
DE1148804B (en) * 1961-03-14 1963-05-16 Bayer Ag Means for protecting against termite damage

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1126374B (en) * 1959-08-27 1962-03-29 Bayer Ag Process for the preparation of alkanolamine salts of salicylanilides
US3074848A (en) * 1960-02-02 1963-01-22 Bayer Ag 2-hydroxy-5,2'-dichloro-4'-nitrobenzanilide for combating tapeworms
DE1148804B (en) * 1961-03-14 1963-05-16 Bayer Ag Means for protecting against termite damage

Also Published As

Publication number Publication date
BE551294A (en)
CH352868A (en) 1961-03-15

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