CH480799A - Pesticides - Google Patents
PesticidesInfo
- Publication number
- CH480799A CH480799A CH37867A CH37867A CH480799A CH 480799 A CH480799 A CH 480799A CH 37867 A CH37867 A CH 37867A CH 37867 A CH37867 A CH 37867A CH 480799 A CH480799 A CH 480799A
- Authority
- CH
- Switzerland
- Prior art keywords
- pesticides
- agents
- dimethyl
- active ingredient
- insecticidal
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 241000254179 Sitophilus granarius Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000254112 Tribolium confusum Species 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- OJZGWRZUOHSWMB-UHFFFAOYSA-L ethoxy-dioxido-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP([O-])([O-])=S OJZGWRZUOHSWMB-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Schädlingsbekämpfungsmittel
Die Herstellung von ss-Alkylmercaptoäthyl-thiophos- phorsäureestern sowie die Verwendung dieser Verbindungen als Wirkstoff für Schädlingsbekämpfungsmittel ist bekannt (DBP 836 349, DBP 850677, DBP 935 432). Diese bekannten Mittel besitzen eine ausgezeichnete kontaktinsektizide und innertherapeutische insektizide Wirkung. Bei längerer Anwendung derartiger Mittel erfolgt jedoch - wie allgemein bekannt - eine Gewöhnung der Schädlinge an die Bekämpfungsmittel, so dass diese allmählich ihre Wirksamkeit verlieren und durch andere wirksamere Mittel ersetzt werden müssen.
Zweck und Aufgabe der vorliegenden Erfindung war es nun, neue Schädlingsbekämpfungsmittel zu finden, deren Wirkstoffe bei einer mit den obengenannten Wirkstoffen gleichwertigen Wirksamkeit eine von diesen abweichende Struktur besitzen.
Es wurde gefunden, dass Schädlingsbekämpfungsmittel, die als aktive Komponente einen ss-Alkoxy äthylmercapto-)alkyl-thiophosphorsäure-dialkylester der Formel
EMI1.1
in der R1, R2, Rg für niedere Alkylreste steht, enthalten, den geforderten Bedingungen entsprechen und eine ausgezeichnete insektizide und akarizide Wirkung besitzen.
Diese bisher noch nicht beschriebenen Verbindungen können nach den allgemein bekannten Herstellungsverfahren, beispielsweise durch Umsetzug von Verbindungen der Formel HOC, H4SC2H4OR mit Dialkylchlorthiophosphaten in Gegenwart säurebindender Mittel, erhalten werden.
Beispiel I
In eine Lösung von 90 g ss-Oxy-ss'-oxyäthyl- diäthyl- sulfid in 150 ml Benzol werden 80 g getrocknetes, feingepulvertes Kaliumcarbonat eingetragen. Man tropft unter Rühren innerhalb 30 Minuten bei 35 C 80 g Dimethylchlorthiophosphat zu und rührt weitere 8 Stunden bei der gleichen Temperatur. Danach wird abgesaugt, 3mal mit je 25 ml Benzol gewaschen, die benzolische Lösung mit Wasser gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel abdestilliert.
Bei einem Vakuum von 5 Torr und einer Badtemperatur von 90 bis 95 OC verbleiben als Destillationsrück- stand 118 g 0,0-Dimethyl-0,2-fl'-äthoxy-äthylmercap- to)-äthylthiophosphat in Form eines schwach gelblich gefärbten, wasserunlöslichen ÖIs. Die Ausbeute beträgt 86 O/o der Theorie.
Beispiel 2
Die insektizide Prüfung des 0, 0-Dimethyl-0,2-(K- äthoxy-äthylmercapto)-äthylthiophosphats erfolgte an Fliegen (Musca domestica), an Kornkäfern (Sitophilus granarius) und Blattläusen (Aoyrthosiphon pisum, Aphis fabae) in Äther gelöst (Angabe der Wirkstoffmenge in 1ig/cm2), an Reismehlkäferlarven (Tribolium confusum) als Wirkstoff im Weizenmehl (Angabe der prozentualen Wirkstoffmenge im Mehl).
Der Wirkungsgrad wurde an Kornkäfern und Fliegen nach achtzehnstündiger, an Blattläsuen nach sechsstündiger und an Reismehlkäferlarven nach zehntägiger Expositionszeit bestimmt.
Anwendung gegen Wirkstoffmenge Wirkungsgrad in g/cm2 bzw.0/o in O/o M. domestica 1,25 45
12,50 100 S. granarius 13 80
130 100 A. pisum 10 60
100 100 A. fabae 100 100 T. confusum 0,01 60
0,025 100
Beispiel 3
Mit Spinnmilben (Tetranychus articae) infizierte Phaseolus-Bohnen wurden mit einer 0,2 0/obigen Lösung eines Präparates behandelt, das 25 O/o 0,0-Dimethyl-0,2- (ss-äthoxy-äthylmercapto)-äthylthiophosphat, 25 O/o Aceton und 50 O/o eines oxäthylierten Alkylphenols enthielt.
Bei der Kontrolle nach 3 Tagen konnte ein nahezu hundertprozentiger Bekämpfungserfolg festgestellt werden.
Pesticides
The preparation of β-alkyl mercaptoethyl thiophosphoric acid esters and the use of these compounds as active ingredients for pesticides is known (DBP 836 349, DBP 850677, DBP 935 432). These known agents have an excellent contact insecticidal and intra-therapeutic insecticidal effect. If such agents are used for a long time, however, as is generally known, the pests get used to the control agents, so that they gradually lose their effectiveness and have to be replaced by other more effective agents.
It was the purpose and object of the present invention to find new pesticides whose active ingredients have a structure that differs from the above-mentioned active ingredients while being effective.
It has been found that pesticides which have an s-alkoxy äthylmercapto-) alkyl-thiophosphoric acid dialkyl ester of the formula
EMI1.1
in which R1, R2, Rg stands for lower alkyl radicals, correspond to the required conditions and have an excellent insecticidal and acaricidal effect.
These hitherto not yet described compounds can be obtained by the generally known production processes, for example by reacting compounds of the formula HOC, H4SC2H4OR with dialkyl chlorothiophosphates in the presence of acid-binding agents.
Example I.
80 g of dried, finely powdered potassium carbonate are added to a solution of 90 g of ss-oxy-ss'-oxyethyl diethyl sulfide in 150 ml of benzene. 80 g of dimethyl chlorothiophosphate are added dropwise with stirring at 35 ° C. over the course of 30 minutes, and the mixture is stirred for a further 8 hours at the same temperature. It is then filtered off with suction, washed 3 times with 25 ml of benzene each time, the benzene solution is washed with water and dried over sodium sulfate and the solvent is distilled off.
At a vacuum of 5 torr and a bath temperature of 90 to 95 ° C., 118 g of 0,0-dimethyl-0,2-fl'-ethoxyethyl mercapto) ethyl thiophosphate remain as distillation residue in the form of a pale yellowish, water-insoluble one Oil. The yield is 86% of theory.
Example 2
The insecticidal test of 0, 0-dimethyl-0,2- (K-ethoxy-äthylmercapto) -äthylthiophosphats was carried out on flies (Musca domestica), on grain beetles (Sitophilus granarius) and aphids (Aoyrthosiphon pisum, Aphis fabae) dissolved in ether ( Specification of the amount of active ingredient in 1ig / cm2), on rice flour beetle larvae (Tribolium confusum) as the active ingredient in wheat flour (information on the percentage of active ingredient in the flour).
The degree of effectiveness was determined on grain weevils and flies after eighteen hours of exposure, on leaf lice after six hours and on rice flour beetle larvae after ten days of exposure.
Use against the amount of active ingredient, efficiency in g / cm2 or 0 / o in O / o M. domestica 1.25 45
12.50 100 S. granarius 13 80
130 100 A. pisum 10 60
100 100 A. fabae 100 100 T. confusum 0.01 60
0.025 100
Example 3
Phaseolus beans infected with spider mites (Tetranychus articae) were treated with a 0.2% above solution of a preparation containing 25% of 0.0-dimethyl-0.2- (ss-ethoxy-ethylmercapto) -ethylthiophosphate, 25% O / o acetone and 50 O / o of an oxethylated alkylphenol.
When checking after 3 days, an almost 100% control success could be determined.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD11897166 | 1966-07-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH480799A true CH480799A (en) | 1969-11-15 |
Family
ID=5478998
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH37867A CH480799A (en) | 1966-07-26 | 1967-01-11 | Pesticides |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH480799A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0215570A1 (en) * | 1985-08-13 | 1987-03-25 | Hironori Kushibiki | Organo phosporic acid dithioester insecticides |
-
1967
- 1967-01-11 CH CH37867A patent/CH480799A/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0215570A1 (en) * | 1985-08-13 | 1987-03-25 | Hironori Kushibiki | Organo phosporic acid dithioester insecticides |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1067016B (en) | Process for the manufacture of organic phosphorus compounds | |
DE2163391A1 (en) | Pesticidal phosphorothiolate compounds | |
DE1135905B (en) | Process for the preparation of thiophosphoric acid esters | |
DE1047776B (en) | Process for the preparation of thionophosphoric acid esters | |
DE1809390A1 (en) | Phosphorus, phosphonic or thionophosphorus (- phosphonic) acid esters and process for their production | |
CH480799A (en) | Pesticides | |
DE1280256B (en) | New O, O-dialkylthionophosphoric acid esters and processes for making the same | |
DE1276638B (en) | O, O-dialkyl-thionophosphoric acid ester | |
DE2118495C3 (en) | Insecticidal agent | |
DE1014988B (en) | Process for the production of neutral thionophosphoric acid triesters | |
DE1642363A1 (en) | Pest repellants | |
AT230394B (en) | Process for the preparation of new organophosphorus compounds | |
CH428704A (en) | Process for the preparation of 0,0-dialkyl-0-dichlorovinyl phosphates | |
DE1057112B (en) | Process for the preparation of thionophosphonic acid esters | |
DE1493569B2 (en) | New aromatic phosphoric or phosphonic acid esters, processes for their preparation and insecticidal and acaricidal agents containing them | |
AT214940B (en) | Process for the preparation of new thiophosphorus, thiophosphonic or thiophosphinic acid esters | |
AT255831B (en) | Pesticides | |
CH532083A (en) | Process for the production of new amidothionophosphoric acid phenyl esters, and their use for the production of insecticidal and acaricidal agents | |
DE2040410C3 (en) | Benzisoxazolo (thiono) phosphorus (phosphonic) acid esters, process for their preparation and their use as insecticides and acaricides | |
AT240102B (en) | Vermin killers | |
DE1955967C (en) | Thiophosphoric acid esters and their use as pesticides | |
DE2045121A1 (en) | Insecticidal and acaricidal composition | |
DE1167845B (en) | Process for the production of phosphoric acid, phosphonic acid and phosphinic acid esters or the corresponding thiono-esters of 5-oxypiazthiol | |
DE1046034B (en) | Process for the preparation of thionophosphoric acid esters | |
DE1171427B (en) | Process for the preparation of thiophosphorus, -phosphonic or -phosphinic acid esters or ester amides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |