DE977119C - Process for the preparation of a pest repellent - Google Patents
Process for the preparation of a pest repellentInfo
- Publication number
- DE977119C DE977119C DEF9944A DEF0009944A DE977119C DE 977119 C DE977119 C DE 977119C DE F9944 A DEF9944 A DE F9944A DE F0009944 A DEF0009944 A DE F0009944A DE 977119 C DE977119 C DE 977119C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- pest repellent
- chloral
- choh
- trichloro
- 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
- 238000000034 method Methods 0.000 title claims 2
- 241000607479 Yersinia pestis Species 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 230000002940 repellent Effects 0.000 title 1
- 239000005871 repellent Substances 0.000 title 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 7
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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)
Description
AUSGEGEBEN AM 11. MÄRZ 1965ISSUED MARCH 11, 1965
F 9944 IVb j 12 οF 9944 IVb j 12 ο
Aus derUSA.-Patentschrift2 48ss73 ist die Herstellung von Kondensationsprodukten aus Chloral und Dialkylphosphiten bekannt. Das Anfangsglied dieser Reihe, der /S.^yS-TrichlO'r-a-oxyäthyldimethylphosphonsäureester, ist jedoch nicht beschrieben.From U.S. Patent 2,48ss73 the manufacture of condensation products from chloral and dialkyl phosphites known. The initial link of this series, the /S.^yS-TrichlO'r-a-oxyäthyldimethylphosphonsäureester, however, it is not described.
Es wurde nun gefunden, daß man zu einem be^ sonders wirksamen Schädlingsbekämpfungsmittel, nämlich dem ^,/J.yS-Trichor-a-oxyäthylphosphonsäuredimethylester gelangt, wenn man Chloral mit Dimethylphosphit umsetzt. Dieses neue Kondensationsprodukt zeigt gegenüber den bekannten Verbindungen sehr günstige insektizide Eigenschaften.It has now been found that one becomes a ^ especially effective pesticides, namely the ^, / J.yS-Trichor-a-oxyäthylphosphonsäuredimethylester when chloral is reacted with dimethyl phosphite. This new condensation product shows very favorable insecticidal properties compared to the known compounds.
Während die höheren Glieder der genannten Reihe wenig wasserlöslich sind, zeigt das Anfangsglied eine ausgesprochene Wasserlöslichkeit, die bei Zimmertemperatur etwa I5fl/o beträgt. Durch diese hohe Wasserlöslichkeit ist es möglich, ohne Zusatz von Emulgatoren wäßrige Lösungen des /?,/?,/J-Trichlora-oxyäthyldimethylphosphonsäureesters direkt zur Schädlingsbekämpfung zu verwenden. Außerdem zeigt das Reaktionsprodukt aus Dimethylphosphit und Chloral gegenüber den bekannten höheren Gliedern eine wesentlich verringerte Giftigkeit gegen Warmblütler. Die insektizide Wirkung, vor allemWhile the higher members of the series mentioned are not very soluble in water, the initial member shows pronounced water solubility, which is about 15 fl / o at room temperature. This high solubility in water makes it possible to use aqueous solutions of /?, /?, / J-trichloro-oxyethyldimethylphosphonic acid ester directly for pest control without the addition of emulsifiers. In addition, the reaction product of dimethyl phosphite and chloral shows a significantly reduced toxicity to warm-blooded animals compared to the known higher members. The insecticidal effects, especially
509 521/7509 521/7
gegen Fliegen, ist gegenüber den vergleichbaren homologen Verbindungen ganz erheblich gesteigert. Folgende Tabelle zeigt die überragende insektizide Wirksamkeit des /^,/^Trichlor-a-oxyathyldimethylphosphonsäureesters im Vergleich zu entsprechend höheren Homologen:against flies, is considerably increased compared to the comparable homologous compounds. The following table shows the outstanding insecticidal effectiveness of the / ^, / ^ trichloro-a-oxyathyldimethylphosphonic acid ester compared to correspondingly higher homologues:
mg/kgMouse subcutaneously
mg / kg
Il O
Il
Cl3C — CHOH — P — (OCH3) 2 Il
Cl 3 C - CHOH - P - (OCH 3 ) 2
IlO
Il
Cl3C — CHOH — P — (OC2Hg)2 Il
Cl 3 C - CHOH - P - (OC 2 Hg) 2
Il O
Il
Cl3C — CHOH — P — (OC3H7) 2 ηIl
Cl 3 C - CHOH - P - (OC 3 H 7 ) 2 η
IlO
Il
Cl3C — CHOH—P — (OC3H7) 2 isoIl
Cl3 C - CHOH-P - (OC 3 H 7) 2 iso
Die Herstellung des /^,/J-Trichlor-a-oxyäthyldimethylphosphonsäureesters kann sehr leicht — vorzugsweise in Abwesenheit inerter Lösungs-The preparation of the / ^, / J-trichloro-a-oxyäthyldimethylphosphonic acid ester can very easily - preferably in the absence of inert solution
Cl3C-CHOCl 3 C-CHO
,0CH3 , 0CH 3
OCH,OCH,
Der neue Ester ist als wenig giftige Wirksubstanz zur Bekämpfung von Fliegen und Bodenschädlingen geeignet.The new ester is a low-toxic active ingredient for combating flies and soil pests suitable.
Zu 4Sog (300 ecm) Chloral (3 Mol), das auf 700 C erwärmt ist, tropft man 360 g (300 ecm) Dimethylphosphit (3,3 Mol) so zu, daß die Temperatur langsam auf 120 bis 1300C ansteigt. Durch eventuelles Kühlen läßt man die Reaktionstemperatur nicht über 1300C steigen. Nach dem Zulauf des Dimethylphosphits wartet man, bis die Temperatur von selbst auf 40 bis 500C gesunken ist und setzt dann 1 1 Tetrachlorkohlenstoff zu. Man kühlt nunmehr auf 5 bis o° C ab. Der körnig ausgeschiedene β,/^/3-Tridilori-a-oxyäthyldimeth.ylphosphonsäureester wird abgesaugt und mit etwas Tetrachlorkohlenstoff gewaschen. Man erhält 708 g des Esters vom Fp. 81 bis 820 C. Ausbeute: 91,5% der Theorie.To 4Sog (300 cc) chloral (3 moles) which is heated to 70 0 C, is added dropwise 360 g (300 cc) of dimethyl phosphite (3.3 mol) so that the temperature slowly rises to 120 to 130 0 C. The reaction temperature is not allowed to rise above 130 ° C. by cooling, if necessary. After the dimethyl phosphite has been fed in, one waits until the temperature has dropped by itself to 40 to 50 ° C. and then 1 liter of carbon tetrachloride is added. It is now cooled to 5 to 0 ° C. The granular β, / ^ / 3-Tridilori-a-oxyäthyldimeth.ylphosphonsäureester precipitated is filtered off with suction and washed with a little carbon tetrachloride. 708 g of the ester with a melting point of 81 to 82 ° C. are obtained. Yield: 91.5% of theory.
150 g Chloral (1 Mol) werden in 330 ecm Tetrachlorkohlenstoff gelöst und auf 700C erwärmt. In rascher Folge tropft man unter Rühren 120 g Dtmethylphosphit zu. Die Temperatur steigt allmäh-150 g of chloral (1 mole) are dissolved in 330 cc of carbon tetrachloride and heated to 70 0 C. 120 g of methylphosphite are added dropwise in rapid succession with stirring. The temperature rises gradually-
mittel — ohne Katalysatoren bei Temperaturen von 20 bis 1300 C nach folgendem Schema durchgeführt werden:medium - carried out without catalysts at temperatures from 20 to 130 0 C according to the following scheme:
Cl3. C — CHOH — P —Cl 3 . C - CHOH - P -
Hch auf 8o° C und wird ι bis 2 Stunden durch Erwärmen dabei gehalten. Nach dem Erkalten und Animpfen kristallisiert der /^,/S-Trichlor-a-oxyäthylphosphonsäuredimethylester aus. Man saugt ab und erhält 159 g des Esters als körniges Kristallpulver in ausgezeichneter Reinheit vom Fp. 850C (61 %>< der Theorie).Hch to 80 ° C. and is kept there for up to 2 hours by heating. After cooling and seeding, the / ^, / S-trichloro-a-oxyäthylphosphonsäuredimethylester crystallizes out. It is filtered off with suction and 159 g of the ester are obtained as a granular crystal powder in excellent purity with a melting point of 85 ° C. (61% of theory).
In 330 ecm Äther werden 150 g (1 Mol) Chloral gelöst. Unter Rühren tropft man 120 g (1,1 Mol) Dimethylph.osph.it zu. Man rührt über Nacht bei Zimmertemperatur, kühlt mit Eiswasser auf 5 bis 100C und saugt das Kristallpulver ab. Man erhält 65 g des jßjySjjS-Trichlor-a-oxyäthylphosphonsäuredimethylesters vom Fp. 850C (25,2% der Theorie).150 g (1 mol) of chloral are dissolved in 330 ecm of ether. 120 g (1.1 mol) of dimethylph.osph.ite are added dropwise with stirring. The mixture is stirred overnight at room temperature, cooled to 5 to 10 ° C. with ice water and the crystal powder is filtered off with suction. This gives 65 g of jßjySjjS-trichloro-a-oxyäthylphosphonsäuredimethylesters mp. 85 C 0 (25.2% of theory).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF9944A DE977119C (en) | 1952-09-20 | 1952-09-21 | Process for the preparation of a pest repellent |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE318818X | 1952-09-20 | ||
| DEF9944A DE977119C (en) | 1952-09-20 | 1952-09-21 | Process for the preparation of a pest repellent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE977119C true DE977119C (en) | 1965-03-11 |
Family
ID=25798699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF9944A Expired DE977119C (en) | 1952-09-20 | 1952-09-21 | Process for the preparation of a pest repellent |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE977119C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2485573A (en) * | 1945-10-05 | 1949-10-25 | Rohm & Haas | Thiocyanated phosphite esters |
-
1952
- 1952-09-21 DE DEF9944A patent/DE977119C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2485573A (en) * | 1945-10-05 | 1949-10-25 | Rohm & Haas | Thiocyanated phosphite esters |
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