DE767153C - Combating animal pests - Google Patents
Combating animal pestsInfo
- Publication number
- DE767153C DE767153C DEJ62070D DEJ0062070D DE767153C DE 767153 C DE767153 C DE 767153C DE J62070 D DEJ62070 D DE J62070D DE J0062070 D DEJ0062070 D DE J0062070D DE 767153 C DE767153 C DE 767153C
- Authority
- DE
- Germany
- Prior art keywords
- animal pests
- acid
- combating animal
- pests
- phosphoric acid
- 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
- 241000607479 Yersinia pestis Species 0.000 title claims description 10
- 241001465754 Metazoa Species 0.000 title claims description 5
- -1 ester compounds Chemical class 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- LTSHICDODAIOSX-UHFFFAOYSA-N CCO[P]OCC Chemical compound CCO[P]OCC LTSHICDODAIOSX-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000131102 Oryzaephilus Species 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 241001151957 Aphis aurantii Species 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001633993 Cineraria Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000517307 Pediculus humanus Species 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
AUSGEGEBEN AM 31. JANUAR 1952ISSUED JANUARY 31, 1952
REICHSPATENTAMTREICH PATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
KLASSE 45 I GRUPPE 3oiCLASS 45 I GROUP 3oi
/ 62070IV a j' 45I / 62070IV aj '45I
Nachträglich gedruckt durch das Deutsche Patentamt in MünchenSubsequently printed by the German Patent Office in Munich
(§20 des Ersten Gesetzes zur Änderung und Überleitung von Vorschriften auf dem Gebiet des gewerblichen Rechtsschutzes vom 8. Juli 1949)(Section 20 of the First Act on the Amendment and Transition of Regulations in the field of industrial property protection from July 8, 1949)
Dr. Gerhard Schrader, Opladen-Bruchhausen undDr. Gerhard Schrader, Opladen-Bruchhausen and
Dr. Hans Kükenthal, LeverkusenDr. Hans Kükenthal, Leverkusen
sind als Erfinder genannt wordenhave been named as inventors
Farbenfabriken Bayer, LeverkusenPaint factories Bayer, Leverkusen
Bekämpfung tierischer SchädlingeControl of animal pests
Patentiert im Deutschen Reich vom 2. August 1Θ38 an Patenterteilung bekanntgemacht am 20. September 1951Patented in the German Empire from August 2, 138 Patent issued September 20, 1951
Es ist bekannt, Trikresylphosphat und seine Homologen als Einreibmittel gegen Kopfläuse zu verwenden. Als Spritzmittel in den üblichen Konzentrationen angewandt, sind diese Verbindungen als Insekticide unwirksam.It is known to oppose tricresyl phosphate and its homologues as a liniment Use head lice. Used as a spray in the usual concentrations, these compounds are ineffective as insecticides.
Demgegenüber wurde gefunden, daß Phosphorsäure- bzw. Phosphorsulfosäurediialkylesterverbindungen der allgemeinen FormelIn contrast, it has been found that dialkyl phosphoric acid or phosphorus sulfonic acid dialkyl ester compounds the general formula
RORO
0(S)0 (S)
/■/ ■
R1O.R 1 O.
Ac in der R und R1 gegebenenfalls substituierte Alky !raste bedeuten und Ac für einen Säurerest steht, wertvolle Mittel zur Bekämpfung tierischer Schädlinge sind. !Ac in which R and R 1 denote optionally substituted alkyls and Ac denotes an acid residue, which are valuable agents for combating animal pests. !
Für R und R1 kann ein beliebiger Alkylrest, z. B. der Methyl-, Äthyl-, Propyl-, Butyl-, Hexyl- oder Dodecylrest, eintreten. Die Alkylreste für R und R1 können z. B. durch Halogenatome oder Alkoxygruppen substituiert sein, R und R1 können für gleiche oder verschiedene Alkylreste stehen. ■For R and R 1 may be any alkyl group, z. B. the methyl, ethyl, propyl, butyl, hexyl or dodecyl radical occur. The alkyl radicals for R and R 1 can, for. B. substituted by halogen atoms or alkoxy groups, R and R 1 can represent the same or different alkyl radicals. ■
An Stelle von Ac kann ein beliebiger an-· organischer oder organischer Säurereist eintreten. Als anorganischer bzw. anorganisch/ organischer Säurerest kommen z. B. Halogen-Any inorganic or organic acid can be used in place of Ac. As an inorganic or inorganic / organic acid residue z. B. Halogen
atome, wie Fluor, Chlor oder Brom, Cyan, Rhodan, oder ein Sulfurvlrest, wieatoms, such as fluorine, chlorine or bromine, cyano, rhodan, or a sulfur radical, such as
0 —0 -
SOoSOo
OR(R = Alkyl),
Ο —OR (R = alkyl),
Ο -
/
SO, OR /
SO, OR
O—P —OR
O ,O — P — OR
O,
SO.,SO.,
oderor
ο ο
R
Ο —R.
Ο -
SO2 RSO 2 R
bzw. ein Phosphorylrest, z. B. des Typs
O Oor a phosphoryl residue, e.g. B. of the type
OO
R2N-P-O-P-OR ,R 2 NPOP-OR,
OROR
S —S -
S = P-OR oder O = P-ORS = P-OR or O = P-OR
OROR
OROR
in Frage.in question.
Organische Acylreste sind z. B. substituierte Formylreste, wie der Rest C2H5OCO-O-, der Acetylrest bzw. substituierte Acetylreste, wie CHsO-CH2-CO-O- oder Cl-CH2-CO-O-, oder Reste höherer Fettsäuren, wie der Oleylrest.Organic acyl radicals are e.g. B. substituted formyl radicals, such as the radical C 2 H 5 OCO-O-, the acetyl radical or substituted acetyl radicals, such as CHsO-CH 2 -CO-O- or Cl-CH 2 -CO-O-, or radicals of higher fatty acids, like the oleyl radical.
Diese Phosphorsäure- bzw. Phosphoirsulfosäuredialkylesterverbindungen sind besonders als Kontaktgifte wirksam. Sie lassen sich vor allem als Spritzmittel zur Insektenbekämpfung, z. B. von Blattläusen, Heu- und Sauerwurm, Kornkäfer und Raupen, verwenden. Es genügen im allgemeinen Konzentrationen von \ 0,02 bis 0,2% der Phosphorsäure- bzw. Phos- jThese phosphoric acid or phosphoirsulfonic acid dialkyl ester compounds are particularly effective as contact poisons. They can be used mainly as a spray for insect control, z. B. of aphids, hayworms, sour worms, grain beetles and caterpillars. There are generally sufficient concentrations of \ 0.02 to 0.2% of phosphoric acid or phosphate j
phorsulfosäuredialkylesterverbindung, um eine ioo°/oige Abtötung der Schädlinge zu erreichen. Irgendwelche Schädigungen der damit in den praktisch in Frage kommenden Konzentrationen behandelten Pflanzen konnten nicht festgestellt werden.Phosulfosäuredialkylesterverbindungen to achieve a 100% killing of the pests. Any damage to the plants treated with it in the practically relevant concentrations could be caused cannot be determined.
Zur Anwendung als Spritzmittel empfiehlt es sich, den zweckmäßig wässerigen Lösungen der genannten Phosphorsäure- bzw. Phosphorsulfosäuredialkylester noch die üblichen Netz- und Dispergierungsmittel zuzusetzen. Als solche kommen z. B. in Frage Kali- und Natronseifen, gewisse alkylierte Xaphtbalinsulfosäuren, Alkoholsulfonate und Einwirkungsprodukte von Alkylenoxyden auf höhermolekulare reaktionsfähige Wasserstoff atome enthaltende Verbindungen.For use as a spray, it is advisable to use the appropriate aqueous solutions of the said phosphoric acid or phosphorus sulfonic acid dialkyl esters add the usual wetting and dispersing agents. As such come z. B. in question potash and Soda soaps, certain alkylated xaphtbalinsulfonic acids, alcohol sulfonates and other products from alkylene oxides to higher molecular weight reactive hydrogen atoms containing compounds.
Sofern die Phosphorsäure- bzw. Phosphorsulf osäuredialkylesterverbindungen vergasbar sind, wie Fluoride, Chloride und Cyanide, gelingt es mit ihrer Hilfe, Schädlinge, z. B. auch Ratten, Mäuse, Hamster, Fliegen, Wanzen, Flöhe, Läuse und Kakerlaken durch Vergasung, sicher zu bekämpfen. Die höhersiedenden Phosphorsäure- bzw. Phosphorsulfosäuredialkylesterverbindungen kann man auch Ködern einverleiben und diese Verbindungen somit auch als Fraßgifte z. B. gegen Mäuse und Ratten verwenden.Provided that the phosphoric acid or phosphoric acid dialkyl ester compounds can be gasified are, such as fluorides, chlorides and cyanides, it is possible with their help to remove pests such. Belly Rats, mice, hamsters, flies, bugs, fleas, lice and cockroaches by gassing, safe to fight. The higher-boiling phosphoric acid or phosphorus sulfonic acid dialkyl ester compounds you can also incorporate bait and thus also use these compounds as food poisons z. B. against mice and Use rats.
Man wußte, daß Triarylphosphate und Triarylphosphoroxyhalogenide fungicide Eigenschäften haben. Höhere aliphatische Ester von Thiophosphorsäuren sollen Parasiticide und Heilmittel sein. Hieraus konnte nicht abgeleitet werden, daß Thiophosphorsäuredialkylesterverbindungen der vorgenannten Formel hervorragend gegen tierische Schädlinge wirken. Trikresylphosphat wirkt gegen Blattläuse selbst in Konzentrationen von 0,5% noch nicht.Triaryl phosphates and triaryl phosphorus oxyhalides were known to have fungicidal properties to have. Higher aliphatic esters of thiophosphoric acids are said to be parasiticides and Be remedies. It could not be deduced from this that thiophosphoric acid dialkyl ester compounds the aforementioned formula are excellent against animal pests. Tricresyl phosphate is effective against aphids not even in concentrations of 0.5%.
π ... ■π ... ■
i. Man bereitet eine wässerige Lösung, die 0,01 % der folgenden Verbindungen enthält unter Zusatz von 0,01% eines Kondensationsproduktes aus ι Mol Dodecylalkohol und 6 Mol Äthylenoxyd. Diese Lösung wird auf Kirschbäumchen, die von schwarzen Blattläusen befallen sind, und auf Apfelbäumchen, die von grünen Blattläusen befallen sind, gespritzt. Nach etwa 24 Stunden ist vollkommene Abtötung der Schädlinge zu beobachten. Schädigung der Pflanzen tritt nicht ein. Es wurden verwendet: 1. Diäthoxyphosphoroxyfluorid, 2. Äthoxymethoxyphosphoroxyfluorid. 3. Äthoxy-n-propoxyphosphoroxyfluorid, 4. Ähtoxy-n-butoxyphosphoroxyfluorid, 5. Äthoxy - ('/J-methoxyäthoxy) - phosphoroxyfluorid, 6. Diäthoxyphosphorsulfosäurefiuorid, 7. Äthoxyisooctyloxyphosphoroxyfluorid, 8. Äthoxyisohexyloxyphosphoroxyfluorid, 9. Äthoxycyclohexyloxyphosphoroxyfluorid, 10. Äthoxy-n-amyloxyphosphoroxyfluori d.i. Prepare an aqueous solution containing 0.01% of the following compounds with the addition of 0.01% of a condensation product of ι mol of dodecyl alcohol and 6 moles of ethylene oxide. This solution is applied to cherry trees by black aphids are infested, and sprayed on apple trees infested by green aphids. Complete destruction of the pests can be observed after about 24 hours. The plants are not damaged. It were used: 1. diethoxyphosphorus oxyfluoride, 2. ethoxymethoxyphosphorus oxyfluoride. 3. ethoxy-n-propoxyphosphorus oxyfluoride, 4. ethoxy-n-butoxyphosphorus oxyfluoride, 5. ethoxy - ('/ J-methoxyethoxy) - phosphorus oxyfluoride, 6. Diethoxyphosphorsulfosäurefiuorid, 7. Äthoxyisooctyloxyphosphoroxyfluorid, 8. ethoxyisohexyloxyphosphorus oxyfluoride, 9. ethoxycyclohexyloxyphosphorus oxyfluoride, 10. Ethoxy-n-amyloxyphosphoroxyfluorine d.
2. In einem 6o cbm großen Zimmer, das mit Fliegen angefüllt ist, werden z. B. 500 mg Diäthoxyphosphoroxyfluorid verstäubt. Nach 1V2 Minuten fallen die ersten Fliegen herunter, nach 7 .Minuten sind auch die letzten Fliegen getötet. Ähnliche Ergebnisse werden erzielt mit ÄthO'xymethoxyphosphoroxyfluorid, Äthoxy - η - propyloxyphosphoiroxyflttorid, Diäthoxyphosphorsulfosäurefluorid.2. In a 6o cbm room that is filled with flies, z. B. 500 mg Diethoxyphosphorus oxyfluoride dusted. After 1 1/2 minutes the first flies fall after 7 minutes the last of the flies are killed. Similar results will be achieved with ÄthO'xymethoxyphosphoroxyfluorid, Äthoxy - η - propyloxyphosphoiroxyflttorid, Diethoxyphosphorus sulfonic acid fluoride.
3. Man stellt eine o,o2%ige wässerige Lösung des Diäthoxyphosphoroxychlorids her, der man 0,02% eines Kondeasationsproduktes aus 1 Mol Dodecylalkohol und 6 Mol Äthylenoxyd zusetzt. Diese Lösung wird auf Kirschbäumchen, die von schwarzen Blattläusen befallen sind, und auf Apfelbäumchen, die von grünen Blattläusen befallen sind, gespritzt. Nach etwa 24 Stunden ist vollkommene Abtötung der Schädlinge zu beobachten.3. One prepares an o, o2% aqueous solution of the diethoxyphosphorus oxychloride, which is 0.02% of a condensation product from 1 mole of dodecyl alcohol and 6 moles of ethylene oxide added. This solution is on Cherry trees that are infested with black aphids and on apple trees, infested with green aphids. After about 24 hours it is perfect Observe the killing of the pests.
Eine Schädigung der Pflanzen tritt nicht ein.The plants are not damaged.
Zu dem gleichen Ergebnis gelangt man beiOne arrives at the same result in
Verwendung 0,02- bis o,o5%iger wässeriger Lösungen von 1. Äthoxymethoxyphosphoroxychlorid, 2.Äthoxypropoxyphosphoroxychlorid,Use 0.02 to 0.05% aqueous solutions of 1. ethoxymethoxyphosphorus oxychloride, 2. ethoxypropoxyphosphorus oxychloride,
3. Äthoxybutoxyphosphoroxychloirid, 4. Äthoxy-^-chloräthoxyphosphoroxychloTid, 5. Äthoxy -(|5-methoxyäthoxy)-phosphotroxychlorid. Ganz ähnlich wirken in Konzentration von 0,2% folgende Verbindungen: 6. Diäthoxyphosphorsulfosäurechlorid, 7. Dipropylo'xyphosphorsulfosäurechlorid, 8. DimethoxyphosphoTsulfosäurechlorid, 9. Di-(/?-metho>xyäthyloxy)-phosphorsulfosäurechlorid. 3. Äthoxybutoxyphosphoroxychloirid, 4. Äthoxy - ^ - chloräthoxyphosphoroxychloTid, 5. Ethoxy (| 5-methoxyethoxy) phosphotroxy chloride. The following compounds have a similar effect in a concentration of 0.2%: 6. 7. Dipropyloxyphosphorsulfosäurechlorid, 8. DimethoxyphosphoTsulfosäurechlorid, 9. Di - (/? - metho> xyäthyloxy) -phosphorosulfonic acid chloride.
4. Eine wässerige Lösung, die 0,02% DiätboxyphosphoiOxycyanid und 0,02% eines gebräuchlichen Netzmittels enthält, wird auf Cinerarien, die von grünen Blattläusen befallen sind, gesprüht. Nach 10 bis 20 Stunden sind die Schädlinge abgetötet. Ähnlich wirken: 1. Cyanphosphoirsulfosäuredipropylester, 2. Cyanphasphorsulfosäureäthylesterpropylester, 3. Cyanphosphorsulfosäureäthylester-(2-methoxy)-äthylester, 4. Cyanphosphorsulfosäurediäthylester. 4. An aqueous solution containing 0.02% diet boxyphosphoioxycyanide and 0.02% of a common wetting agent is applied Cineraria that are infested with green aphids, sprayed. After 10 to 20 hours the pests are killed. The following have a similar effect: 1. Dipropyl cyanophosphorus sulfate, 2. ethyl cyanophosphorus sulfate propyl ester, 3. ethyl cyanophosphorus sulfate (2-methoxy) ethyl ester, 4. Diethyl cyanophosphorus sulfate.
5. In einem geschlossenen Raum von 1 cbm Inhalt befinden sich Fliegen, Raupen, Kornkäfer und £ine Maus. Es werden 500 mg des Diäthoxyphosphoroxycyaniids in dem Raum zerstäubt. Nach iV2 Minuten sind alle Insekten getötet. Nach etwa 4 bis 5 Minuten geht auch die Maus ein.5. Flies, caterpillars, grain beetles and a mouse are in a closed room with a capacity of 1 cbm. 500 mg of the diethoxyphosphorus oxycyanide are atomized into the room. All insects are killed after 2 minutes. The mouse dies after about 4 to 5 minutes.
6. Als Spritzmittel in Konzentration von 0,02 bis 0,05% wirksamer Verbindungen wirken gegen Raupen, Blattläuse und Kornkäfer die folgenden Verbindungen:6. As a spray in a concentration of 0.02 to 0.05% active compounds the following compounds act against caterpillars, aphids and grain beetles:
CH, 0CH, 0
CH3OCH 3 O
P-S-P-OCH3 PSP-OCH 3
OCH,OCH,
i.i.
(CEy8N-P-O- P- OC2H5 (CEy 8 NPO- P- OC 2 H 5
SO9 SUN 9
OC2H5 OC 2 H 5
0-P-OC2H5 OC2H5 0-P-OC 2 H 5 OC 2 H 5
/
0-P-OC2H5 /
0-P-OC 2 H 5
Oc2H5 0 Oc 2 H 5 0
OC2H5 0OC 2 H 5 O
CH3-SO2-O-P-OC2H5 CH 3 -SO 2 -OP-OC 2 H 5
OC2H5 OC 2 H 5
(CHg)2N-SO2-O-P-OC2H5 (CHg) 2 N-SO 2 -OP-OC 2 H 5
• \• \
OC2H5 OC 2 H 5
C2H5OC 2 H 5 O
C2H5OC 2 H 5 O
C2H5OC 2 H 5 O
C2H5O 0-CO-CH3 C 2 H 5 O 0-CO-CH 3
0-CO-OC2H5 O-CO-OC 2 H 5
3-3-
5-5-
6.6th
7-7-
C2H5O 0C 2 H 5 O 0
0-CO-CH,0-CO-CH,
C2H5OC 2 H 5 O
CH3OCH 3 O
CH3OCH 3 O
0-OC-(CHo)7-CH = CH-C8H17 (Oleyl)0-OC- (CHo) 7 -CH = CH-C 8 H 17 (oleyl)
Ρ—S—Ρ —OCH,Ρ — S — Ρ —OCH,
OCH,OCH,
ίο.ίο.
ΐ5 Die genannten Verbindungen sind zum Teil bekannt. Die Herstellung der Dialkoxyphosphoroxychloride erfolgt z. B. nach »Annalen der Chemie und Pharmazie«, Supplementband VI, 1865, S. 257 bis 280, die der Dialk- oxyphosphoroxyfiuori.de z. B. nach »Berichte 65«, S. 1598, die der Pyrothiophosphoorsäureester nach Carius, »Zur Theorie der mehrbasischen Säuren«, Heidelberg, 1861, S. 62ff. Die anderen Verbindungen lassen sich z. B. durch Umsetzen von Säurechloriden mit den vorzugsweise neutralen Estern von Phosphorbzw. Phosphorsulfosäuren herstellen.ΐ5 Some of the connections mentioned are known. The preparation of the Dialkoxyphosphoroxychloride takes place z. B. after »Annals of chemistry and pharmacy ", Supplementary Volume VI, 1865, pp. 257 to 280, which the dialk oxyphosphoroxyfiuori.de z. B. according to "Reports 65", p. 1598, that of the pyrothiophosphoric acid ester according to Carius, »On the theory of polybasic Acids ", Heidelberg, 1861, p. 62ff. The other connections can be z. B. by reacting acid chlorides with the preferably neutral esters of Phosphorbzw. Manufacture phosphorus sulfonic acids.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEJ62070D DE767153C (en) | 1938-08-02 | 1938-08-02 | Combating animal pests |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEJ62070D DE767153C (en) | 1938-08-02 | 1938-08-02 | Combating animal pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE767153C true DE767153C (en) | 1952-01-31 |
Family
ID=7207545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ62070D Expired DE767153C (en) | 1938-08-02 | 1938-08-02 | Combating animal pests |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE767153C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072703A (en) * | 1959-04-01 | 1963-01-08 | Exxon Research Engineering Co | Preparation of organo and inorgano phosphorus complexes suitable for sulfating and sulfonating organic compounds |
| US3075874A (en) * | 1959-05-15 | 1963-01-29 | Monsanto Chemicals | Mixed anhydrides of aromatic disulfonic acids and dialkylphosphorothioates |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE462688C (en) * | 1925-01-22 | 1928-07-16 | I G Farbenindustrie Akt Ges | Insecticides |
| US2063629A (en) * | 1935-02-19 | 1936-12-08 | Du Pont | Esters of the thio acids of phosphorus |
| US2071017A (en) * | 1936-07-13 | 1937-02-16 | Dow Chemical Co | Aryl phosphoric acid halides |
| US2071323A (en) * | 1935-01-19 | 1937-02-23 | Dow Chemical Co | Organic phosphates and method of making same |
-
1938
- 1938-08-02 DE DEJ62070D patent/DE767153C/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE462688C (en) * | 1925-01-22 | 1928-07-16 | I G Farbenindustrie Akt Ges | Insecticides |
| US2071323A (en) * | 1935-01-19 | 1937-02-23 | Dow Chemical Co | Organic phosphates and method of making same |
| US2063629A (en) * | 1935-02-19 | 1936-12-08 | Du Pont | Esters of the thio acids of phosphorus |
| US2071017A (en) * | 1936-07-13 | 1937-02-16 | Dow Chemical Co | Aryl phosphoric acid halides |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072703A (en) * | 1959-04-01 | 1963-01-08 | Exxon Research Engineering Co | Preparation of organo and inorgano phosphorus complexes suitable for sulfating and sulfonating organic compounds |
| US3075874A (en) * | 1959-05-15 | 1963-01-29 | Monsanto Chemicals | Mixed anhydrides of aromatic disulfonic acids and dialkylphosphorothioates |
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