DE958968C - Pest repellants - Google Patents
Pest repellantsInfo
- Publication number
- DE958968C DE958968C DEF16106A DEF0016106A DE958968C DE 958968 C DE958968 C DE 958968C DE F16106 A DEF16106 A DE F16106A DE F0016106 A DEF0016106 A DE F0016106A DE 958968 C DE958968 C DE 958968C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- acid ester
- dimethyl
- flies
- phenylthiophosphoric
- 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 description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 241000255925 Diptera Species 0.000 description 9
- 150000003014 phosphoric acid esters Chemical class 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 6
- 241000257159 Musca domestica Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 3-chloro-phenylthiophosphoric acid ester Chemical class 0.000 description 1
- ZEFMBAFMCSYJOO-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)phenol Chemical compound OC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 ZEFMBAFMCSYJOO-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- NZNRRXXETLSZRO-UHFFFAOYSA-N chlorthion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(Cl)=C1 NZNRRXXETLSZRO-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
In der Schädlingsbekämpfung nimmt die Vernichtung sogenannter hygienischer Schädlinge einen breiten Raum ein. Die Bekämpfung der als Überträgerin mancher Krankheiten bekannten Hausfliege (Musca domestica) wird auf breitester Basis durchgeführt, und zwar wurden hierbei im letzten Jahrzehnt bevorzugt Kontaktinsektizide aus der Reihe der chlorierten Kohlenwasserstoffe verwendet. Resistenzerscheinungen zwangen jedoch zur Suche nach immer neuen Mitteln. Auch organische Phosphorsäureester wurden für die sogenannte hygienische Schädlingsbekämpfung in Betracht gezogen. In pest control, the destruction of so-called hygienic pests occupies a large area. The control of the house fly (Musca domestica), which is known to be the carrier of some diseases, is carried out on a very broad basis, and in the last decade contact insecticides from the range of chlorinated hydrocarbons have been preferred. However, signs of resistance forced the search for new remedies. Organic phosphoric acid esters have also been considered for so-called hygienic pest control.
In neuester Zeit sind nun neutrale Phosphorsäureester bekanntgeworden, die bei einer sehr guten Insektiziden Wirkung für Warmblüter verhältnismäßig ungiftig sind, so unter anderem der O, O-Dimethyl-O - 4 - nitro-3 - chlor - phenylthiophosphorsäureester mit einer letalen Dosis von 500 mg/kg Ratte.Recently, neutral phosphoric acid esters are now available became known, which is relatively with a very good insecticidal effect for warm-blooded animals are non-toxic, including O, O-dimethyl-O - 4 - nitro-3 - chloro - phenylthiophosphoric acid ester with a lethal dose of 500 mg / kg rat.
Es wurde nun gefunden, daß Schädlingsbekämpfungsmittel mit einem Gehalt an einer Verbindung der allgemeinen FormelIt has now been found that pesticides containing a compound of the general formula
Alkyl—O,Alkyl-O,
Alkyl —O'Alkyl —O '
.Ρ—X.Ρ — X
NO,NO,
worin X = O oder S und Alkyl = Methyl, Äthyl, Propyl oder Butyl bedeutet, gegenüber den bisher bekannten Phosphorsäureestern bedeutende Fortschrittewhere X = O or S and alkyl = methyl, ethyl, propyl or butyl means significant advances over the previously known phosphoric acid esters
bringen. So ist z. B. das O, O-Dimethyl-O^-nitro-s-trifluormethyl-phenylthiophosphat bei gleicher Toxizität für Warmblüter dem entsprechenden 3-Chlor-phenylthiophosphorsäureester in der Wirksamkeit auf Fliegen etwa sechs- bis zehnfach überlegen, wie aus den nachstehenden Beispielen hervorgeht. Von besonderer Bedeutung ist hierbei die Tatsache, daß es mit den neuen Produkten auch in Aerosolform gelingt, eine Dauerwirksamkeitzu erzielen, wie sie bei den Vergleichs-Substanzen nicht beobachtet werden kann.bring. So is z. B. the O, O-dimethyl-O ^ -nitro-s-trifluoromethyl-phenylthiophosphate with the same toxicity for warm-blooded animals the corresponding 3-chloro-phenylthiophosphoric acid ester about six to ten times superior in effectiveness on flies, as shown in the following Examples. Of particular importance here is the fact that it is with the new products, also in aerosol form, succeed in achieving a long-term effectiveness, as is the case with the comparison substances cannot be observed.
Man kann zu den Verbindungen der obigen Formel gelangen, wenn man die entsprechenden O, O-Dialkylthiophosphorsäurechloride in bekannter Weise mit 4-Nitro-3-trifluormethylphenol umsetzt.The compounds of the above formula can be obtained by using the corresponding O, O-dialkylthiophosphoric acid chlorides Reacts in a known manner with 4-nitro-3-trifluoromethylphenol.
Die Verbindungen können auch für die allgemeine Schädlingsbekämpfung eingesetzt werden, z. B. als Spritz-, Stäube-, Streumittel oder Lösung, gegebenenfalls in Kombination mit anderen Schädlingsbekämpfungsmitteln oder Synergisten.The compounds can also be used for general pest control, e.g. B. as Spray, dust, grit or solution, possibly in combination with other pesticides or synergists.
Will man im Petrischalentest mit 1 ecm acetonischer Lösung pro Halbschale erreichen, daß binnen 30 Minuten Einwirkungszeit bei 210 sämtliche Fliegen (Musca domestica) in dauernder Rückenlage sind, so genügt hierzu bei O, O-Dimethyl-O-s-trifluormethyM-nitrophenyl-thiophosphorsäureester und O, O-Diäthyl-O-3-trinuormethyl-4-nitro-phenylthiophosphorsäureester eine Konzentration der Lösung von 0,005 °/o-Im Vergleich hierzu ist für O, O-Dimethyl-O-4-nitro-3-chlor-phenylthiophosphat 0,05% erforderlich, also die zehnfache Konzentration.If one wishes to achieve in the Petri dish test with 1 cc of acetone solution per half-shell, that within 30 minutes of exposure time at 21 0 all fly (Musca domestica) in constant supine position are so this is sufficient for O, O-dimethyl-O-trifluormethyM-nitrophenyl-thiophosphoric and O, O-diethyl-O-3-trinuomethyl-4-nitro-phenylthiophosphoric acid ester has a concentration of 0.005% in the solution .05% required, i.e. ten times the concentration.
Durch Auflösen von o,i°/0 O, O-Dimethyl-O-3-trifluormethyl-4-nitro-phenylthiophosphorsäureesteroder O, O-Diäthyl-O-s-trmuormethyl^-nitro-phenylthiophosphorsäureester in Petroleum erhält man Sprühmittel, die in einer Aufwandmenge von 2 cm3/m3RaumBy dissolving o, i ° / 0 , O-dimethyl-O-3-trifluoromethyl-4-nitro-phenylthiophosphoric acid ester or O, O-diethyl-Os-trmuormethyl ^ -nitro-phenylthiophosphoric acid ester in petroleum, sprays are obtained which are applied in one application rate of 2 cm 3 / m 3 space
z. B. Musca domestica in 15 bis 30 Minuten in fortbewegungsunfähigen Zustand versetzen.z. B. Musca domestica immobilized in 15 to 30 minutes Move state.
Vergleicht man diese Wirkung mit der von O, O-Dimethyl - O-4-nitro - 3 - chlor - phenylthiophosphat unter gleichen Bedingungen, so stellt man fest, daß von letzteren eine mehr als fünffache Konzentration erforderlich ist.If one compares this effect with that of O, O-dimethyl - O-4-nitro - 3 - chloro - phenylthiophosphate under the same conditions, it is found that of the latter a more than fivefold concentration is required.
Die Prozentzahlen der in dauernder Rückenlage befindlichen Fliegen im Alter von 4 Tagen bei 270 zeigt folgende Tabelle:The percentage of flies in the supine position at the age of 4 days at 27 0 is shown in the following table:
O, O-Dimethyl-O-3-trinuormethyl-4-nitro-phenylthio- O, O-dimethyl-O-3-trinuomethyl-4-nitro-phenylthio-
phosphorsäureester 0.1%phosphoric acid ester 0.1%
O, O-Diäthyl-O-3-trifluormethyl-4-nitro-phenylthio- O, O-diethyl-O-3-trifluoromethyl-4-nitro-phenylthio-
phosphorsäureester °>lO/ophosphoric acid esters °> 10 / o
O, O-Dirnethyl-O-4-nitro-3-chlor-phenylthiophosphorsäureester 0,5 %O, O-Dimethyl-O-4-nitro-3-chlorophenylthiophosphoric acid ester 0.5%
95 97 7395 97 73
9696
9999
9797
9797
9999
97 Ein Vergleich bei 230 zwischen O, O-Dimethyl-O -3 - trifluor-methyl-4-nitro-phenylthiophosphorsäureesterund O, O-Diäthyl-O-s-trifluor-methyl^-nitro-phenylthiophosphorsäureester einerseits und der gleichen und doppelten Konzentration von O, O-Dimethyl-O^-nitro-s-chlor-phenylthiophosphorsäureester andererseits ist aus folgender Tabelle ersichtlich: 97 A comparison at 23 0 between O, O-dimethyl-O -3 - trifluoro-methyl-4-nitro-phenylthiophosphoric acid ester and O, O-diethyl-Os-trifluoro-methyl ^ -nitro-phenylthiophosphoric acid ester on the one hand and the same and double concentration of O, O-dimethyl-O ^ -nitro-s-chloro-phenylthiophosphoric acid ester, on the other hand, can be seen from the following table:
O, O-Dimethyl-O-3-trinuormethyl-4-nitro-phenylthio- O, O-dimethyl-O-3-trinuomethyl-4-nitro-phenylthio-
phosphorsäureester 0.1%phosphoric acid ester 0.1%
O, O-Diäthyl-O-3-trinuormethyl-4-nitro-phenylthio- O, O-diethyl-O-3-trinuomethyl-4-nitro-phenylthio-
phosphorsäureester 0,1 %phosphoric acid ester 0.1%
O, O-Dimethyl-O-4-nitro-3-chlor-phenylthiophosphor- O, O-dimethyl-O-4-nitro-3-chlorophenylthiophosphorus
säureester 0.2%acid ester 0.2%
O, O-Dimethyl-O-4-nitro-3-chlor-phenylthiophosphorsäureester °»lO/oO, O-Dimethyl-O-4-nitro-3-chloro-phenylthiophosphoric acid ester - 10 / o
NachTo
15 I 30 I 45 Minuten15 I 30 I 45 Minutes
3737
2323
93 99 77 5893 99 77 58
9999
100100
8888
8282
Ähnliche, zum Teil noch größere Unterschiede ergeben sich, wenn man die Substanzen in wäßriger Emulsion versprüht.Similar, in some cases even greater, differences emerge when the substances are mixed with water Sprayed emulsion.
Ein Aerosol zur Bekämpfung von Fliegen und anderen Insekten läßt sich herstellen, indem man 5 Gewichtsteile O, O-Dimethyl-O-s-trifluormethyl^-nitrophenylthiophosphorsäureester mit 6,5 Teilen Petroleum und 3,5 Teilen Dipenten mischt und mit dieser Lösung und 85 Gewichtsteilen Dichlordifluormethan als Treibmittel Niederdruck-Aerosoldosen in der Kälte füllt. Entläßt man aus diesen Dosen z. B. im geschlossenen Raum 0,3 g Aerosol pro m3 Luftraum, so erreicht man, daß z. B. bei einer Raumtemperatur von 22° die Hälfte der Fliegen (Musca domestica) nach 15 Minuten, etwa 90 % nach 25 Minuten und der Rest spätestens bis zum Ablauf einer Stunde bewegungsunfähig am Boden liegen und ohne besondere Erregung schnell absterben. Besonders wertvoll ist, daß diese »*o geringen Aerosolmengen den Raum auf längere Zeit für Ungeziefer, wie Fliegen, unbewohnbar machen. Selbst nach mehrstündiger Lüftung gehen Fliegen, die an den folgenden Tagen in einen so behandelten Raum gekommen sind, binnen weniger Stunden in derselben "5 unauffälligen Weise zugrunde.An aerosol for combating flies and other insects can be prepared by mixing 5 parts by weight of O, O-dimethyl-Os-trifluoromethyl ^ -nitrophenylthiophosphoric acid ester with 6.5 parts of petroleum and 3.5 parts of dipentene and with this solution and 85 parts by weight of dichlorodifluoromethane as a propellant fills low-pressure aerosol cans in the cold. If you discharge from these doses z. B. in a closed space 0.3 g aerosol per m 3 of air space, it is achieved that z. B. at a room temperature of 22 ° half of the flies (Musca domestica) after 15 minutes, about 90% after 25 minutes and the remainder are immobile on the ground by an hour at the latest and die quickly without any particular excitement. It is particularly valuable that these small amounts of aerosol make the space uninhabitable for a long time for vermin such as flies. Even after several hours of ventilation, flies that enter a room treated in this way on the following days perish within a few hours in the same inconspicuous manner.
Ein entsprechendes Aerosol mit O, O-Dimethyl-O - 4- nitro - 3 - chlor - phenylthiophosphorsäureester als wirksame Substanz wirkt unter gleichen Umständen schon zu Anfang wesentlich langsamer, so daß nach iao einer halben Stunde noch keine spürbare Erleichterung eingetreten und nach einer Stunde keine Fliegenfreiheit erreicht ist. Besetzt man ein mit O, O-Dimethyl-O^-nitro-s-chlor-phenylthiophosphorsäureester in der angegebenen Weise behandeltes Zimmer nach 3 Tagen mit Fliegen und hält Fenster und Türen geschlossen,A corresponding aerosol with O, O-dimethyl-O - 4-nitro-3-chloro-phenylthiophosphoric acid ester as an active substance acts under the same circumstances already at the beginning much slower, so that after iao Half an hour there was still no noticeable relief and after an hour no freedom from flies is reached. If one is occupied with O, O-dimethyl-O ^ -nitro-s-chlorophenylthiophosphoric acid ester Room treated in the specified manner after 3 days with flies and keeps windows and doors closed,
so nehmen selbst nach weiteren 24 Stunden die Fliegen kaum ab.so the flies hardly decrease even after a further 24 hours.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF16106A DE958968C (en) | 1954-11-10 | 1954-11-11 | Pest repellants |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE339426X | 1954-11-10 | ||
DEF16106A DE958968C (en) | 1954-11-10 | 1954-11-11 | Pest repellants |
Publications (1)
Publication Number | Publication Date |
---|---|
DE958968C true DE958968C (en) | 1957-02-28 |
Family
ID=25817323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF16106A Expired DE958968C (en) | 1954-11-10 | 1954-11-11 | Pest repellants |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE958968C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1208115B (en) * | 1959-09-03 | 1965-12-30 | Sumitomo Chemical Co | Insecticides |
-
1954
- 1954-11-11 DE DEF16106A patent/DE958968C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1208115B (en) * | 1959-09-03 | 1965-12-30 | Sumitomo Chemical Co | Insecticides |
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