DE665214C - Fighting and driving away insects and insect larvae - Google Patents
Fighting and driving away insects and insect larvaeInfo
- Publication number
- DE665214C DE665214C DEG92135D DEG0092135D DE665214C DE 665214 C DE665214 C DE 665214C DE G92135 D DEG92135 D DE G92135D DE G0092135 D DEG0092135 D DE G0092135D DE 665214 C DE665214 C DE 665214C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- alkyl
- fighting
- substituted
- insect larvae
- 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
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Description
Bekämpfen und Vertreiben von Insekten und Insektenlarven Es wurde gefunden, daß Verbindungen, die in ihrem Molekül die Atomgruppierung mit einem 5- oder 6gliedrigen Ring enthalten, wertvolle Insektenbekäxripfungs- und -vertreibungsmittel darstellen.Control and repel insects and insect larvae It has been found that compounds that in their molecule the atomic grouping with a 5- or 6-membered ring, are valuable insect protection and repellants.
In dieser Formel bedeuten X die ringschließende, ein- oder zweigliedrige, gesättigte oder ungesättigte, unsubstituierte oder substituierte Kohlenstoffbrücke, die zugleich Glied von weiteren Ringsystemen sein kann, und R -O-Alkyl, -O-Aralkyl oder deren Substitutionsprodukte, -NH=, -NH-Alkyl, -NH-Aryl, -NH-Cycloalkyl oder entsprechende einfach oder gemischt substituierte, tertiäre Aminogruppen, Ureido-, Guanylreste oder stickstoffhaltige Ringsysteme oder gesättigte oder ungesättigte, einfache oder substituierte Alkyl-oder Arylgruppen.In this formula, X denotes the ring-closing, one- or two-membered, saturated or unsaturated, unsubstituted or substituted carbon bridge, which can also be a member of other ring systems, and R -O-alkyl, -O-aralkyl or their substitution products, -NH =, -NH-alkyl, -NH-aryl, -NH-cycloalkyl or corresponding mono- or mixed substituted, tertiary amino groups, ureido, Guanyl residues or nitrogen-containing ring systems or saturated or unsaturated, simple or substituted alkyl or aryl groups.
Solche Verbindungen sind beispielsweise
Man hat schon substituierte Kondensationsprodukte ungesättigter aromatischer Oxysäuren als Insektenvertreibungsmittel vorgeschlagen. Darunter fallen Halogensubstitutionsprodukte des Cumarins oder dessen Homologen oder deren Derivate; Stoffe, die alle einen substituierten Pyronring enthalten. Genannt werden Fluor-, Brom-, Chlor-, Alkyl-, Aryl- und Thiocumarine. Der erfindungsgemäß verwendete Verbindungstyp kann als ein a,-Keto-y-lakton aufgefaßt werden, wobei jedoch zur Erzielung der ausgezeichneten Wirksamkeit an das a-ständige Kohlenstoffatom noch eine weitere -CO-Gruppe gebunden sein muß. Es ergibt sich aus der chemischen Struktur der schon als Insektenbekämpfungsmittel vorgeschlagenen Cumarinderivate im Vergleich mit den erfindungsgemäß anzuwendenden a-Ketotetronsäuren (a-Carbonyltetro-nsäuren) ohne weiteres der grundsätzliche Unterschied. Die ausgezeichnet wirkende Dehydracetsäure z. B. verhält sich chemisch völlig anders als ein Cumarin. Das gleiche gilt für die x-ketosubstituierten Tetronsäuren.Substituted condensation products of unsaturated aromatic compounds are already present Oxy acids proposed as insect repellants. This includes halogen substitution products of coumarin or its homologues or their derivatives; Substances that all have a substituted one Pyron ring included. Fluorine, bromine, chlorine, alkyl, aryl and thiocoumarins are mentioned. The type of compound used in the present invention can be construed as an α, -keto-γ-lactone be, however, to achieve the excellent effectiveness to the a-standing Another -CO group must be bonded to the carbon atom. It arises from the chemical structure of those already proposed as insect control agents Coumarin derivatives in comparison with the α-ketotetronic acids to be used according to the invention (a-Carbonyltetro-nsäuren) without further ado the fundamental difference. The excellent acting dehydracetic acid z. B. behaves chemically completely different than a coumarin. The same applies to the x-keto-substituted tetronic acids.
Aus nachstehender Zusammenstellung ergibt sich die Wirksamkeit der
a-Ketotetronsäuren verglichen mit den schon für die Insektenbekämpfung und -vertreibung
benutzten Cumarinderivaten. Es wurde eine 2 °/oige alkoholische Lösung hergestellt,
ungefärbter Wollstoff damit getränkt, abgeschleudert, getrocknet und überall eine
gleiche Anzahl Mottenlarven angesetzt. - Nach einigen Tagen wurden Exkremente und
Fraßspuren beurteilt.
Außerdem sind die a-Ketotetronsäuren mit der menschlichen Haut verträglicher (Halogencumarine erzeugen nach A n s c h ü t z , Annalen der Chemie, 36;, S. toi, auf der Haut Bläschen und starken Juckreiz), zudem sind sie vollständig farblos, was im Vergleich zum gelb gefärbten Thiocumarin hervorzuheben ist; der letzte Umstand ist besonders .,wichtig für die Verwendung dieser Insektenvertreibungsmittel auf Textilien.In addition, the a-ketotetronic acids are more compatible with human skin (According to A n s c hü t z, Annalen der Chemie, 36 ;, S. toi, blisters and severe itching on the skin), and they are completely colorless, which should be emphasized in comparison to the yellow colored thiocoumarin; the last circumstance is especially., important to the use of these insect repellants Textiles.
Die Anwendung der obengenannten Insektenvertreibungs- und -bekämpfungsmittel kann nach üblichen Verfahren erfolgen. Lösungen in Wasser oder in billigen organischen Lösungsmitteln können zum Bestreichen, Bespritzen oder Tauchen der zu schützenden Stoffe und Textilien dienen, sie dürfen auch zerstäubt werden, ohne daß schädliche Wirkungen für den Warmblüter festzustellen sind. Pelze, Federn oder Wolle mit solchen Lösungen behandelt, können so dauernd gegen den Angriff von Motten geschützt werden. Zum gleichen Ergebnis führt die Ausfällung der wirksamen Stoffe auf den zu schützenden Gegenstand aus alkalischer Lösung durch Säure. Werden Pflanzenschädlinge bespritzt, so läßt sich beispielsweise an Fliegen oder Stabheuschrecken leicht feststellen, daß die Wirkung der Mittel auch als Berührungsgift sehr gut ist.The use of the above-mentioned insect repellants and control agents can be done according to standard procedures. Solutions in water or in cheap organic ones Solvents can be used for brushing, spraying or dipping the to be protected Substances and textiles are used, they can also be atomized without causing harmful effects Effects for the warm-blooded animal can be determined. Furs, feathers, or wool with them Treated solutions can thus be permanently protected against attack by moths. The precipitation of the active substances on those to be protected leads to the same result Object made from alkaline solution by acid. If plant pests are sprayed, For example, it is easy to determine on flies or stick insects, that the effect of the means is also very good as a poison to the touch.
Ebenso können die Mittel als Lösungen oder Emulsionen in Ölen, Fetten, Cremen oder als Zusätze zu Pulvern für die Zwecke der Insektenabwehr und -bekämpfung angewendet werden.The agents can also be used as solutions or emulsions in oils, fats, Creams or as additives to powders for the purpose of repelling and controlling insects be applied.
Beispiel i , Man löst 2 Teile Dehydracetsäure in 98 Teilen Alkohol, behandelt Pelze, Federn oder Wolle beispielsweise durch Tauehen, schleudert und trocknet. Die so belinä'elte Ware ist mottenecht. Es genügen scl `verdünntere Lösungen, um einen befriede enden Schutz vor Mottenfraß zu erzielen. .Example i, 2 parts of dehydracetic acid are dissolved in 98 parts of alcohol, treats furs, feathers or wool, for example by thawing, spins and dries. The goods so belinä''elte are moth-proof. It suffices `More dilute solutions, in order to achieve a satisfactory protection against moth damage. .
Verwendet man statt der oben angegebenen Dehydracetsäure Tetronsäurederivate, wie Dichlorbenzo- oder Benzotetronsäurecarbonsäureester, beispielsweise die Methyl-, Äthyl-, Propyl- oder Amylester, obenerwähnte a-ketosubstituierteTetronsäurederivate, wieKetone, Carbonsäureamide, Anilide oder Diäthyläthylendiamide, so erzielt man eine gleichwertige Wirkung.If tetronic acid derivatives are used instead of the dehydracetic acid specified above, such as dichlorobenzo- or benzotetronic acid carboxylic acid esters, for example the methyl, Ethyl, propyl or amyl esters, the abovementioned a-keto-substituted tetronic acid derivatives, such as ketones, carboxamides, anilides or diethylethylenediamides, this is how one achieves an equivalent effect.
Bestimmte Schädlinge, wie Stabheuschrekken, werden durch das Bespritzen mit den. oben angegebenen alkoholischen Lösungen getötet. Die genannten Verbindungen können auch als gute Berührungsgifte gegen Fliegen verwendet werden.Certain pests, such as stick insects, are prevented from being sprayed with the. Above specified alcoholic solutions killed. The mentioned connections can also be used as good touch poisons against flies.
Beispiel z Man stellt eine konzentrierte, wäßrige Lösung der in Beispiel i angegebenen Verbindungen mit Hilfe von Alkalien her, taucht die zu behandelnden Stoffe und säuert ab, wodurch ebenfalls ein befriedigender Schutz vor Insektenfraß erzielt wird.Example z A concentrated, aqueous solution of the in example is prepared i specified compounds with the help of alkalis, immersed the to be treated Substances and acidifies, which also provides a satisfactory protection against insect damage is achieved.
Claims (1)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEG92135D DE665214C (en) | 1936-02-08 | 1936-02-08 | Fighting and driving away insects and insect larvae |
US123061A US2127879A (en) | 1936-02-08 | 1937-01-29 | Textile or the like pestproofing medium and use |
FR817182D FR817182A (en) | 1936-02-08 | 1937-02-01 | Method for combating insects and their larvae as well as agents intended for this purpose |
GB3605/37A GB478398A (en) | 1936-02-08 | 1937-02-06 | Improvements in or relating to rendering materials moth-proof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEG92135D DE665214C (en) | 1936-02-08 | 1936-02-08 | Fighting and driving away insects and insect larvae |
Publications (1)
Publication Number | Publication Date |
---|---|
DE665214C true DE665214C (en) | 1938-09-21 |
Family
ID=25979208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEG92135D Expired DE665214C (en) | 1936-02-08 | 1936-02-08 | Fighting and driving away insects and insect larvae |
Country Status (4)
Country | Link |
---|---|
US (1) | US2127879A (en) |
DE (1) | DE665214C (en) |
FR (1) | FR817182A (en) |
GB (1) | GB478398A (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487179A (en) * | 1946-08-23 | 1949-11-08 | Thompson Boyce Plant Res | Organic compounds |
US2474227A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Making carbohydrate foods resistant to microorganisms |
US2567010A (en) * | 1947-01-13 | 1951-09-04 | Dow Chemical Co | Fungistatic wrapper |
DE967185C (en) * | 1947-01-13 | 1957-10-17 | Dow Chemical Co | Packaging or wrapping material, especially for food |
US2474228A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Making proteinaceous and fatty foods resistant to microorganisms |
US2596107A (en) * | 1948-12-04 | 1952-05-13 | Schieffelin & Co | Use of carbalkoxy hydroxy benzo-coumarin against fungi |
US2652399A (en) * | 1950-10-24 | 1953-09-15 | Sterling Drug Inc | Tertiary-aminoalkyl derivatives of coumarilic acids and their preparation |
NL111039C (en) * | 1958-10-01 | |||
US3859312A (en) * | 1972-12-21 | 1975-01-07 | Richardson Merrell Inc | 6h-dibenzo(b,d)pyran-6-ones |
US4078075A (en) * | 1976-09-20 | 1978-03-07 | Ciba-Geigy Corporation | Insecticidally active 3-N-(4-trifluoromethylphenyl)-carbamoyl-4-hydroxy-coumarin |
US5985912A (en) * | 1996-12-20 | 1999-11-16 | Pfizer Inc. | 4-hydroxy coumarin derivatives |
-
1936
- 1936-02-08 DE DEG92135D patent/DE665214C/en not_active Expired
-
1937
- 1937-01-29 US US123061A patent/US2127879A/en not_active Expired - Lifetime
- 1937-02-01 FR FR817182D patent/FR817182A/en not_active Expired
- 1937-02-06 GB GB3605/37A patent/GB478398A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR817182A (en) | 1937-08-27 |
US2127879A (en) | 1938-08-23 |
GB478398A (en) | 1938-01-18 |
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