DE1003494B - Pest repellants - Google Patents
Pest repellantsInfo
- Publication number
- DE1003494B DE1003494B DEF14486A DEF0014486A DE1003494B DE 1003494 B DE1003494 B DE 1003494B DE F14486 A DEF14486 A DE F14486A DE F0014486 A DEF0014486 A DE F0014486A DE 1003494 B DE1003494 B DE 1003494B
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- compounds
- pest repellants
- pesticides
- content
- 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
Links
- 241000607479 Yersinia pestis Species 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical compound C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 claims 1
- 241000118205 Ovicides Species 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
- PEXKIPRKGNEQPD-UHFFFAOYSA-N 1,2-dichloro-3-(2,2,2-trichloro-1-phenylethyl)benzene Chemical compound ClC=1C(=C(C=CC=1)C(C(Cl)(Cl)Cl)C1=CC=CC=C1)Cl PEXKIPRKGNEQPD-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- -1 B. octachlor-1 Chemical class 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YUQZCZNRGWZEQQ-UHFFFAOYSA-N ClC1(C(C2(C(C3=CC=CCC13)(C2)Cl)Cl)(Cl)Cl)Cl Chemical compound ClC1(C(C2(C(C3=CC=CCC13)(C2)Cl)Cl)(Cl)Cl)Cl YUQZCZNRGWZEQQ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/38—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with three condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Schädlingsbekämpfungsmittel Es wurde gefunden, daß ungesättigte Verbindungen der allgemeinen Formel wobei X für H oder Halogen, mindestens 4 Halogenatome und Hal für Halogen steht, z. B. Oktachlor-1, 4-endomethylen-oktahydronaphthalin, vorzüglich zur Bekämpfung von tierischen Schädlingen geeignet sind.Pesticides It has been found that unsaturated compounds of the general formula where X is H or halogen, at least 4 halogen atoms and Hal is halogen, e.g. B. octachlor-1, 4-endomethylene-octahydronaphthalene, are particularly suitable for combating animal pests.
Derartige Verbindungen können z. B. folgendermaßen durch Umsetzung von Halocyclopentadien mit Cyclohexadien und anschließende Halogenierung erhalten werden: 272 g Hexachlorcyclopentadien werden mit 500 g Toluol gemischt und nach Zusatz von 140 g Cyclohexadien-1, 3 in einer Bombe auf etwa 140° erhitzt. Nach 24 Stunden ist die Reaktion beendet, das Addukt Hexachlormethano-hexahydronaphthalin wird durch Abdestillieren des Lösungsmittels vorzugsweise unter vermindertem Druck isoliert und in einem inerten Lösungsmittel in Gegenwart eines Chlorüberträgers, z. B. Jod, FeCls oder A1C13, oder unter UV-Licht-Bestrahlung so lange chloriert, bis 2 Chloratome aufgenommen sind.Such compounds can be, for. B. by implementation as follows obtained from halocyclopentadiene with cyclohexadiene and subsequent halogenation are: 272 g of hexachlorocyclopentadiene are mixed with 500 g of toluene and after Addition of 140 g of cyclohexadiene-1,3 heated to about 140 ° in a bomb. After 24 The reaction is complete for hours, the adduct hexachloromethanohexahydronaphthalene is made by distilling off the solvent, preferably under reduced pressure isolated and in an inert solvent in the presence of a chlorine carrier, z. B. iodine, FeCls or A1C13, or chlorinated under UV light irradiation for as long as until 2 chlorine atoms are added.
Die Herstellung der genannten Verbindungen ist nicht Gegenstand des vorliegenden Schutzrechts.The production of the compounds mentioned is not part of the present property right.
Die Verbindungen gemäß der obigen Formel eignen sich zur Vernichtung verschiedenartiger Insekten und Milben, und zwar sowohl fressender als auch saugender Schädlinge in der Land- und Forstwirtschaft sowie von Vorrats-oder sogenannten hygienischen Schädlingen und übertreffen in ihrer Wirkung die Mittel auf der Basis von Dichlordiphenyltrichlormethylmethan. Die Substanzen können für sich allein oder in der üblichen Weise unter Zusatz von Lösungs-, Emulgier-, Netz-, Haft- und Trägerstoffen als Spritz-, Stäube-, Streumittel oder in anderen bekannten Formen verwendet werden, gegebenenfalls in Mischung mit anderen Insektiziden, Acariziden, Synergisten oder Fungiziden. Für warmblütige Tiere sind die Verbindungen ungefährlich.The compounds according to the above formula are suitable for destruction of various insects and mites, both eating and sucking Pests in agriculture and forestry as well as from storage or so-called hygienic Pests and outperform the means based on dichlorodiphenyltrichloromethylmethane in their effect. The substances can be used alone or in the customary manner with the addition of Solvents, emulsifiers, wetting agents, adhesives and carriers as spraying, dusting and scattering agents or in other known forms, optionally mixed with other insecticides, acaricides, synergists or fungicides. For warm-blooded animals the connections are harmless.
Im Gegensatz zu den erfindungsgemäßen Verbindungen weisen die des USA.-Patents 2 655 513 eine zusätzliche Sauerstoffbrücke und eine weitere Doppelbindung auf. Ihrer LDbo von 50 bis 100 mg (Ratte) steht die LDSO von etwa 200 bis 300 mg der neuen Verbindungen vorteilhaft gegenüber, die außerdem eine erhöhte insektizide Wirksamkeit zeigen. Die Verbindungen gemäß dem USA.-Patent 2 657 165 besitzen eine Endoäthylenbrücke und keine Doppelbindung. Sie sind nach den Angaben der Patentschrift nur insektizid wirksam. Abgesehen von einer überlegenen Wirksamkeit gegen Fliegen sind die neuen Verbindungen auch akarizid wirksam, so daß sie sich zur Bekämpfung von Rote Spinne, Vogelmilben und Zecken eignen.In contrast to the compounds according to the invention, the des USA.-Patent 2,655,513 an additional oxygen bridge and a further double bond on. Your LDbo of 50 to 100 mg (rat) stands for the LDSO of around 200 to 300 mg the new compounds advantageous over, which also have increased insecticidal properties Show effectiveness. The compounds of U.S. Patent 2,657,165 have one Endoethylene bridge and no double bond. They are according to the specifications of the patent specification only effective as an insecticide. Apart from a superior effectiveness against flies The new compounds are also acaricidally active, so that they can be used to combat from red spiders, poultry mites and ticks.
Beispiel 1 Ein Spritzpulver aus 15 °/o Oktachlor-1, 4-endomethylen-oktahydronaphthalin, 200/, einer kolloiden Kieselsäure, 10 °/o Zellpech, 10/, eines Kondensationsproduktes einer höhermolekularen Fettsäure mit Methyltaurin, hochkonz., und 540/, Kreide tötet Raupen, z. B. von Schwammspinner (Lymantria dispar), die mit einer Suspension von 1 °/o dieses Spritzpulvers bespritzt werden, binnen weniger Stunden ab.EXAMPLE 1 A wettable powder made from 15% octachloro-1,4-endomethylene-octahydronaphthalene, 200%, a colloidal silica, 10% cell pitch, 10 %, a condensation product of a higher molecular weight fatty acid with methyl taurine, high concentration, and 540 /, Chalk kills caterpillars, e.g. B. of gypsy moth (Lymantria dispar), which are sprayed with a suspension of 1% of this wettable powder, within a few hours.
Beispiel 2 Ein emulgierbares Spritzmittel läßt sich herstellen, indem man 30 °/o des im Beispiel 1 genannten Wirkstoffs in 50 °/o Dioxan löst und mit 20 °/o oxäthyliertem Alkylphenol als Netzmittel versetzt. Emulsionen aus dieser Mischung sind insektizid und acarizid, z. B. gegen Raupen, Blattläuse und Rote Spinne (Tetranychus-Arten).Example 2 An emulsifiable spray composition can be produced by 30% of the active ingredient mentioned in Example 1 is dissolved in 50% of dioxane and mixed with 20% oxethylated alkylphenol was added as a wetting agent. Emulsions from this Mixture are insecticidal and acaricidal, e.g. B. against caterpillars, aphids and red spiders (Tetranychus species).
Beispiel 3 Ein Stäubemittel aus 5 °/o des im Beispiel 1 genannten Wirkstoffs, 15 °/o hydratisierter Kieselsäure und Rest Talkum eignet sich für die Einstäubung von lagerndem Getreide mit Beizapparaten oder Schaufeln gegen Befall durch Kornkäfer (Calandra granaria). Im Verhältnis 1 : 1000 dem Getreide gleichmäßig beigemischt, macht ein solches Stäubemittel die Kornkäfer binnen eines Tages unschädlich. Es übertrifft dabei in der Stärke und Schnelligkeit der Wirkung entsprechende Zubereitungen auf der Basis von Dichlordiphenyltrichlormethylmethan.Example 3 A dust made from 5% of that mentioned in Example 1 Active ingredient, 15% hydrated silica and the remainder talc is suitable for the Dusting of stored grain with pickling devices or shovels against infestation by grain weevils (Calandra granaria). In a ratio of 1: 1000 to the grain evenly mixed in, such a dust renders the grain beetles harmless within a day. It surpasses the corresponding preparations in terms of strength and speed of action based on dichlorodiphenyltrichloromethylmethane.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF14486A DE1003494B (en) | 1954-04-17 | 1954-04-17 | Pest repellants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF14486A DE1003494B (en) | 1954-04-17 | 1954-04-17 | Pest repellants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1003494B true DE1003494B (en) | 1957-02-28 |
Family
ID=7087617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF14486A Pending DE1003494B (en) | 1954-04-17 | 1954-04-17 | Pest repellants |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1003494B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115244B (en) * | 1958-10-29 | 1961-10-19 | Hoechst Ag | Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) -yl- (5) -cyclo-propane compounds suitable for pest control |
| DE1150242B (en) * | 1955-11-21 | 1963-06-12 | Benzol Products Company | Insect repellants |
| DE1254147B (en) * | 1962-02-22 | 1967-11-16 | Sankyo Co | Process for the preparation of insecticidally active 1, 9, 10, 11, 12, 12-hexachloro-tricyclo- [7, 2, 1, 0] -dodeca-3, 6, 10-triene |
-
1954
- 1954-04-17 DE DEF14486A patent/DE1003494B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1150242B (en) * | 1955-11-21 | 1963-06-12 | Benzol Products Company | Insect repellants |
| DE1115244B (en) * | 1958-10-29 | 1961-10-19 | Hoechst Ag | Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) -yl- (5) -cyclo-propane compounds suitable for pest control |
| DE1254147B (en) * | 1962-02-22 | 1967-11-16 | Sankyo Co | Process for the preparation of insecticidally active 1, 9, 10, 11, 12, 12-hexachloro-tricyclo- [7, 2, 1, 0] -dodeca-3, 6, 10-triene |
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