DE1093361B - Process for the production of new pest control agents - Google Patents
Process for the production of new pest control agentsInfo
- Publication number
- DE1093361B DE1093361B DEF22101A DEF0022101A DE1093361B DE 1093361 B DE1093361 B DE 1093361B DE F22101 A DEF22101 A DE F22101A DE F0022101 A DEF0022101 A DE F0022101A DE 1093361 B DE1093361 B DE 1093361B
- Authority
- DE
- Germany
- Prior art keywords
- production
- pest control
- control agents
- water
- new pest
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 241000607479 Yersinia pestis Species 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- ACZVWYLTJHGUCP-UHFFFAOYSA-N n-(2,2,2-trichloro-1-hydroxyethyl)formamide Chemical compound ClC(Cl)(Cl)C(O)NC=O ACZVWYLTJHGUCP-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 diaryl phosphites Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- LVFUWJLIDMSANU-UHFFFAOYSA-N methoxy(methylsulfanyl)phosphinous acid Chemical compound COP(O)SC LVFUWJLIDMSANU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LOHIPRQJOOCJAD-UHFFFAOYSA-N N-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)formamide Chemical compound CN(C=O)C(C(Cl)(Cl)Cl)O LOHIPRQJOOCJAD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 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
-
- 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
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
Verfahren zur Herstellung von neuen Schädlingsbekämpfungsmitteln Die Herstellung von zur Schädlingsbekämpfung dienenden Phosphonsäureestern aus Chloral und Dialkylphosphiten ist bekannt, besonders ist der ß,ß,ß-Trichlor-a-oxyäthyl-phosphonsäuredimethylester beschrieben worden. Process for the manufacture of new pesticides The production of pest control phosphonic acid esters from chloral and dialkyl phosphites are known, in particular the ß, ß, ß-trichloro-a-oxyethyl-phosphonic acid dimethyl ester has been described.
Es wurde nun gefunden, daß man zu neuen Schädlingsbekämpfungsmitteln mit besonders günstigen Eigenschaften gelangt, wenn man Dialkyl- oder Diarylphosphite bzw. -thiophosphite mit Additionsprodukten aus Chloral und Formamide der Formel in der Y für Wasserstoff oder einen anderen Substituenten steht, umsetzt. Die so entstehenden neuen Verbindungen besitzen bei hoher insektizider Wirkung nur geringfügige Giftigkeit gegen Warmblüter und sind deshalb als Schädlingsbekämpfungsmittel besonders geeignet. Ferner haben die Verfahrensprodukte Bedeutung als innere Therapeutika für Warmblüter. Sie sind teils wasserlöslich, teils in Wasser unlöslich.It has now been found that new pesticides with particularly favorable properties are obtained if dialkyl or diaryl phosphites or thiophosphites are used with addition products of chloral and formamides of the formula in which Y is hydrogen or another substituent. The resulting new compounds have a high insecticidal effect and are only slightly toxic to warm-blooded animals and are therefore particularly suitable as pesticides. The products of the process are also important as internal therapeutics for warm-blooded animals. They are partly soluble in water and partly insoluble in water.
Die hergestellten neuen Verbindungen lassen sich leicht in Abwesenheit von Wasser und in Gegenwart oder Abwesenheit inerter Lösungsmittel bei Temperaturen zwischen 0 und 1500C ohne Verwendung besonderer Reaktionsbeschleuniger in teilweise vorzüglicher Ausbeute herstellen. Bevorzugt werden jedoch die Verfahrensprodukte entweder bei Zimmertemperatur in Äther oder Methanol oder in Abwesenheit von Lösungsmitteln bei Temperaturen von 100 bis 130"C hergestellt. The new compounds made can easily be in the absence of water and in the presence or absence of inert solvents at temperatures between 0 and 1500C without the use of special reaction accelerators in part produce excellent yield. However, the products of the process are preferred either at room temperature in ether or methanol, or in the absence of solvents manufactured at temperatures of 100 to 130 "C.
Die genaue Konstitution der Verfahrensprodukte ist bisher nicht bekannt, so daß der überraschende Vorteil der auffallend geringen Giftigkeit der neuen Produkte bei gleichzeitig guter insektizider Wirkung vorläufig nicht erklärbar ist. The exact constitution of the process products is not yet known, so that the surprising advantage of the remarkably low toxicity of the new products with a good insecticidal effect at the same time cannot be explained for the time being.
Die zu verwendenden Diester entsprechen der Formel in der R1 und R2 Alkyl- oder Arylreste und X Sauerstoff oder Schwefel bedeuten. Derartige Diester sind ebenfalls bekannt.The diesters to be used correspond to the formula in which R1 and R2 are alkyl or aryl radicals and X is oxygen or sulfur. Such diesters are also known.
Besonders sind die verfahrensgemäß unter Verwendung von Dimethylphosphit oder Dimethylthiophosphit und Chloralformamid hergestellten Verbindungen ausgezeichnete Schädlingsbekämpfungsmittel bzw. innere Therapeutika für Warmblüter. Particularly are those according to the method using dimethyl phosphite or dimethylthiophosphite and chloralformamide are excellent Pesticides and internal therapeutics for warm-blooded animals.
Beispiel 1 Zu einer Lösung vcn 88,0 g Chloralformamid in 200,0 ccm Äther tropft man bei Zimmertemperatur unter Rühren 60,0 g Dimethylphosphit, rührt das Gemisch bei gleicher Temperatur noch 8 Stunden und läßt es über Nacht stehen. Das danach unter der Ätherschicht angesammelte Reaktionsprodukt wird abgetrennt und einmal mit trockenem Äther nachgewaschen. Es ist eine nicht destillierbare, honiggelbe, sirupartige, klare Flüssigkeit, die sich in jedem Verhältnis leicht in kaltem Wasser löst. Die Ausbeute von 44,4 g entspricht 30 °/0 der Theorie. Example 1 To a solution of 88.0 g of chloralformamide in 200.0 cc Ether is added dropwise to 60.0 g of dimethyl phosphite at room temperature with stirring, and the mixture is stirred the mixture at the same temperature for 8 hours and left to stand overnight. The reaction product then accumulated under the ethereal layer is separated off and washed once with dry ether. It is a non-distillable one honey-yellow, syrupy, clear liquid that is easy in any proportion dissolves in cold water. The yield of 44.4 g corresponds to 30% of theory.
Beispiel 2 88,0 g Chloralformamid schmilzt man allmählich auf einem Ölbad und tropft bei einer Temperatur von 100 bis 110"C langsam unter Rühren 60,0 g Dimethylphosphit hinzu. Dabei steigt die Temperatur allmählich an. Durch Wasserkühlung verhindert man, daß 130"C überschritten werden und rührt nach dem Abstellen der Kühlung die Mischung bis zum freiwilligen Erkalten der Reaktionsmasse. Man erhält 148,0 g einer klaren, gelben, sirupartigen Flüssigkeit, die sich leicht in jedem Verhältnis mit Wasser mischen läßt. Die Ausbeute beträgt 100°/o der Theorie. Example 2 88.0 g of chloralformamide are gradually melted on a Oil bath and drop at a temperature of 100 to 110 "C slowly with stirring 60.0 g dimethyl phosphite added. The temperature rises gradually. By water cooling prevents 130 "C from being exceeded and stirs after switching off the Cool the mixture until the reaction mass cools down voluntarily. You get 148.0 g of a clear, yellow, syrupy liquid that easily dissolves in any Mix ratio with water. The yield is 100% of theory.
Beispiel 3 88,0 g Chloralformamid schmilzt man allmählich auf dem Ölbad und tropft bei 100 bis 110°C unter Rühren langsam 70,0 g Dimethylthiophosphit hinzu. Man verfährt im übrigen nach dem Beispiel 2 und erhält schließlich 158,0 g einer dunkelbraunen, sirupartigen Flüssigkeit, die in Wasser unlöslich, in organischen Lösungsmitteln dagegen gut löslich ist. Die Ausbeute entspricht 1000/, der Theorie. Example 3 88.0 g of chloralformamide are gradually melted on the Oil bath and 70.0 g of dimethylthiophosphite are slowly added dropwise at 100 to 110 ° C. with stirring added. The rest of the procedure is as in Example 2 and finally 158.0 is obtained g of a dark brown, syrupy liquid that is insoluble in water, in organic Solvents on the other hand is readily soluble. The yield corresponds 1000 /, the theory.
Beispiel 4 96,0 g Chloralformamid werden am Rückflußkühler mit 117,0 g Diphenylphosphit und 25,0 ccm 100/gerNatriummethylatlösung verrührt und dabei allmählich auf 80"C erwärmt. Die Temperatur steigt plötzlich auf 140"C an. Example 4 96.0 g of chloralformamide are added to the reflux condenser at 117.0 g of diphenyl phosphite and 25.0 cc of 100 / ger sodium methylate solution are stirred together gradually heated to 80 "C. The temperature suddenly rises to 140" C.
Anschließend wird die Mischung noch 1 Stunde bei 1200C nachgerührt. Das Reaktionsprodukt wird mit Aceton versetzt, das ausgefallene Natriummethylat abgesaugt und durch Vakuumdestillation wieder vom Aceton befreit. Das erhaltene Produkt ist eine durchsichtige braune, viskose Flüssigkeit, die leicht nach Phenol riecht, in Wasser nicht, in Alkoholen und Ketonen gut löslich ist.The mixture is then stirred for a further 1 hour at 120.degree. The reaction product is mixed with acetone, the precipitated sodium methylate suctioned off and freed from acetone again by vacuum distillation. The received Product is a translucent brown, viscous liquid that is slightly phenolic smells, not in water, is readily soluble in alcohols and ketones.
Die Ausbeute entspricht der Theorie.The yield corresponds to the theory.
Beispiel 5 103,0 g N-Methyl-chloralformamid werden geschmolzen und unter Rückfluß mit 60,0 g Dimethylphosphit und 2,0 ccm 10°/Oiger Natriummethylatlösung verrührt, wobei die Temperatur selbsttätig auf 45" C ansteigt. Anschließend wird die Mischung 1 Stunde bei 120"C nachgerührt. Nach dem Abkühlen der Mischung erhält man in theoretischer Ausbeute eine sirupartige gelbe Flüssigkeit, die sich in Wasser, Alkoholen und Ketonen löst. Example 5 103.0 g of N-methylchloralformamide are melted and under reflux with 60.0 g of dimethyl phosphite and 2.0 ccm of 10% sodium methylate solution stirred, the temperature rising automatically to 45 "C. Then is the mixture is subsequently stirred at 120 ° C. for 1 hour. After cooling, the mixture is obtained one in theoretical Yield a syrupy yellow liquid that dissolves in water, Dissolves alcohol and ketones.
PITENTANSPROCHE: 1. Verfahren zur Herstellung von neuen Schädlingsbekämpfungsmitteln, dadurch gekennzeichnet, daß man Dialkyl- oder Diarylphosphite bzw. -thiophosphite mit Additionsprodukten aus Chloral und Formamiden der Formel in der Y für Wasserstoff oder einen anderen Substituenten steht, umsetzt.PITENTANSPROCHE: 1. Process for the preparation of new pesticides, characterized in that dialkyl or diaryl phosphites or thiophosphites with addition products of chloral and formamides of the formula in which Y is hydrogen or another substituent.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22101A DE1093361B (en) | 1957-01-10 | 1957-01-10 | Process for the production of new pest control agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22101A DE1093361B (en) | 1957-01-10 | 1957-01-10 | Process for the production of new pest control agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1093361B true DE1093361B (en) | 1960-11-24 |
Family
ID=7090322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF22101A Pending DE1093361B (en) | 1957-01-10 | 1957-01-10 | Process for the production of new pest control agents |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1093361B (en) |
-
1957
- 1957-01-10 DE DEF22101A patent/DE1093361B/en active Pending
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