CH497124A - Organic phosphorus cpd used as pesticide - Google Patents
Organic phosphorus cpd used as pesticideInfo
- Publication number
- CH497124A CH497124A CH8061A CH8061A CH497124A CH 497124 A CH497124 A CH 497124A CH 8061 A CH8061 A CH 8061A CH 8061 A CH8061 A CH 8061A CH 497124 A CH497124 A CH 497124A
- Authority
- CH
- Switzerland
- Prior art keywords
- pesticide
- organic phosphorus
- hours
- compound
- cpd used
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims abstract description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 2
- 239000011574 phosphorus Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 abstract description 2
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- VPXIGHWTJSUAIH-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)acetamide Chemical compound COCCNC(=O)CCl VPXIGHWTJSUAIH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 244000046052 Phaseolus vulgaris 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
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000005406 washing 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
- 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
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
Abstract
Organic phosphorus cpd. used as pesticide Cpds. of formula (CH3O)2 -S-CH2-CO-NH-C2H4-O-CH3 are used to destroy insects and acarides during their various stages of development.
Description
Schädlingsbekämpfungsmittel
Im Hauptpatent Nr. 392 981 werden Schädlingsbekämpfungsmittel beschrieben, die als aktive Komponente eine organische Phosphorverbindung der Formel
EMI1.1
enthalten, worin R und R1 Alkyl-, Cycloalkyl-, Aralkyl-, Aryl- oder heterocyclische Reste bedeuten, wobei R und R1 auch Glieder eines Ringsystems sein können, R2 einen durch mindestens ein Sauerstoffatom oder ein Schwefelatom unterbrochenen Alkylrest oder einen Aryloxyalkylrest und R3 Wasserstoff, einen Alkylrest oder den gleichen Rest wie R2 bedeuten.
Es wurde nun gefunden, dass man mit Mitteln, die als aktive Komponente die Verbindung der Formel
EMI1.2
enthalten, genau so gute Ergebnisse zur Bekämpfung von Schädlingen erhält.
Die neue Verbindung ist vor allem zur Bekämpfung von schädlichen Insekten und Akariden geeignet, deren verschiedene Entwicklungsstufen wie Eier, Larven, Imagines vernichtet werden. Die Wirkung tritt sowohl als Kontakt- wie als Frassgift ein.
Für die Art der Herstellung der Verbindung 1 sowie für ihre Formulierung zu Schädlingsbekämpfungsmitteln gilt das im Hauptpatent Gesagte. Die Verbindung kann als einziger Wirkstoff in einem Schädlingsbekämpfungsmittel vorhanden sein oder auch in Kombination mit anderen Insektiziden und/oder Fungiziden.
Herstellungsbeispiel
19,8 g K-Salz der Dimethylthiolphosphorsäure werden in 40 ml Aceton gelöst. Dazu gibt man bei Raumtemperatur eine Lösung von 15,2 g Chloressigsäuremethoxyäthylamid in 20 ml Aceton, rührt eine Stunde lang bei Raumtemperatur und anschliessend 3 Stunden bei 40450 C, filtriert vom ausgeschiedenen KC1 ab und dampft das Filtrat im Vakuum bei 35400 C ein. Nach dem Aufnehmen des Rückstands in Methylenchlorid, Waschen mit NaHCOs-Lösung und Wasser und Trocknen über Na2SO4 zieht man das Lösungsmittel im Vakuum ab.
Als Rückstand erhält man 22,3 g der Verbindung der Formel
EMI1.3
als Öl, das sich im Hochvakuum bei 0,12 Torr und 133-135 C destillieren lässt.
Analyse: S berechnet 12,46 % gefunden 11,9 %
Biologisches Beispiel
A) Man vermischt 2 Teile der Verbindung der Formel (1) mit 1 Teil des Kondensationsproduktes aus 1 Mol tert.-Octylphenol und 8 Mol Äthylenoxyd und 7 Teilen Isopropanol. Man erhält eine klare Lösung, die als Spritzmittelkonzentrat verwendet werden kann und sich durch Eingiessen in Wasser emulgieren lässt.
1. Zur Feststellung der Kontakwirkung auf Blattläuse wurde folgender Versuch durchgeführt, wobei Spritzbrühen mit 0,08, 0,04, 0,02 und 0,01% Wirkstoffgehalt verwendet wurden.
Puff-Bohnen, die stark mit Blattläusen befallen waren, wurden allseitig gespritzt und nach 48 Stunden und 96 Stunden kontrolliert. Wenn bei der ersten Kontrolle vollständige Abtötung beobachtet wurde, fand eine Neubesiedlung der Pflanze mit Blattläusen statt.
Folgendes Resultat wurde erzielt: Konz. des Wirkstoffs Kontaktwirkung auf Blattläuse in der Spritzbrühe nach 48 Std. nach 96 Std.
0,08 % 100 % 100 %
0,04 % 100% 100 %
0,02 % 100% 100 %
0,01% 100 % 100 %
B) Zur Feststellung der Penetrationswirkung wurden die Bohnenpflanzen nur von oben in Richtung der Sprossachse mit der Wirkstofflösung übersprüht. In diesem Falle werden die an den Blattunterseiten sitzenden Versuchstiere nicht vom Sprühstrahl getroffen. Die aktive Substanz wirkt durch Penetration auf die Schädlinge.
Nach 48 Stunden wurden folgende prozentuale Abtötungen für die angegebenen Wirkstoffkonzentrationen erzielt:
Konz. des Wirkstoffs Penetration nach in der Spritzbrühe 48 Stunden 0,08 % 100%
0,04 % 100%
0,02 % 100% 0,01% 100%
Pesticides
In the main patent no. 392 981 pesticides are described, which as an active component an organic phosphorus compound of the formula
EMI1.1
contain, wherein R and R1 are alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radicals, where R and R1 can also be members of a ring system, R2 is an alkyl radical interrupted by at least one oxygen atom or a sulfur atom or an aryloxyalkyl radical and R3 is hydrogen , an alkyl radical or the same radical as R2.
It has now been found that, with agents which act as the active component, the compound of the formula
EMI1.2
contain just as good results for pest control.
The new compound is particularly suitable for combating harmful insects and acarids, the various stages of their development such as eggs, larvae and imagines are destroyed. The effect occurs both as a contact poison and as a food poison.
The statements made in the main patent apply to the type of preparation of compound 1 and to its formulation into pesticides. The compound can be present as the only active ingredient in a pesticide or else in combination with other insecticides and / or fungicides.
Manufacturing example
19.8 g of the K salt of dimethylthiol phosphoric acid are dissolved in 40 ml of acetone. A solution of 15.2 g of chloroacetic acid methoxyethylamide in 20 ml of acetone is added at room temperature, the mixture is stirred for one hour at room temperature and then for 3 hours at 40450 C, the precipitated KC1 is filtered off and the filtrate is evaporated in vacuo at 35400 C. After taking up the residue in methylene chloride, washing with NaHCOs solution and water and drying over Na2SO4, the solvent is removed in vacuo.
The residue obtained is 22.3 g of the compound of the formula
EMI1.3
as an oil that can be distilled in a high vacuum at 0.12 torr and 133-135 ° C.
Analysis: S calculated 12.46%, found 11.9%
Biological example
A) 2 parts of the compound of formula (1) are mixed with 1 part of the condensation product of 1 mol of tert-octylphenol and 8 mol of ethylene oxide and 7 parts of isopropanol. A clear solution is obtained which can be used as a spray concentrate and which can be emulsified by pouring it into water.
1. To determine the contact effect on aphids, the following experiment was carried out using spray liquors with 0.08, 0.04, 0.02 and 0.01% active ingredient content.
Broad beans that were heavily infested with aphids were sprayed on all sides and checked after 48 hours and 96 hours. If complete kill was observed at the first control, aphid repopulation took place.
The following result was achieved: Conc. Of the active ingredient Contact effect on aphids in the spray mixture after 48 hours after 96 hours.
0.08% 100% 100%
0.04% 100% 100%
0.02% 100% 100%
0.01% 100% 100%
B) To determine the penetration effect, the bean plants were sprayed with the active ingredient solution only from above in the direction of the stem axis. In this case, the test animals sitting on the underside of the leaves are not hit by the spray jet. The active substance acts on the pests through penetration.
After 48 hours, the following percentage deaths were achieved for the specified active ingredient concentrations:
Conc. Of the active ingredient penetration after 48 hours in the spray mixture 0.08% 100%
0.04% 100%
0.02% 100% 0.01% 100%
Claims (1)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH8061A CH497124A (en) | 1960-02-24 | 1961-01-04 | Organic phosphorus cpd used as pesticide |
ES0265153A ES265153A1 (en) | 1960-02-24 | 1961-02-23 | Procedure for the preparation of new organic phosphorous compounds (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH207660A CH392981A (en) | 1960-02-24 | 1960-02-24 | Pesticides |
CH8061A CH497124A (en) | 1960-02-24 | 1961-01-04 | Organic phosphorus cpd used as pesticide |
Publications (1)
Publication Number | Publication Date |
---|---|
CH497124A true CH497124A (en) | 1970-10-15 |
Family
ID=25683437
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH8061A CH497124A (en) | 1960-02-24 | 1961-01-04 | Organic phosphorus cpd used as pesticide |
Country Status (2)
Country | Link |
---|---|
CH (1) | CH497124A (en) |
ES (1) | ES265153A1 (en) |
-
1961
- 1961-01-04 CH CH8061A patent/CH497124A/en not_active IP Right Cessation
- 1961-02-23 ES ES0265153A patent/ES265153A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES265153A1 (en) | 1961-08-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |