DE1642260C3 - Thiophosphoric acid esters, process for their preparation and pesticides containing them - Google Patents
Thiophosphoric acid esters, process for their preparation and pesticides containing themInfo
- Publication number
- DE1642260C3 DE1642260C3 DE19671642260 DE1642260A DE1642260C3 DE 1642260 C3 DE1642260 C3 DE 1642260C3 DE 19671642260 DE19671642260 DE 19671642260 DE 1642260 A DE1642260 A DE 1642260A DE 1642260 C3 DE1642260 C3 DE 1642260C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- acid esters
- mol
- thiophosphoric acid
- methyl
- 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
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000575 pesticide Substances 0.000 title description 3
- 238000000034 method Methods 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- -1 propargyloxycarbonyl Chemical group 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZSQZLMGTNQMFAH-UHFFFAOYSA-N 2-hydroxypyrazolo[4,3-d]pyrimidine Chemical class N1=CN=CC2=NN(O)C=C21 ZSQZLMGTNQMFAH-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- LXCIHXPVYQKJAG-UHFFFAOYSA-N N-[aziridin-1-yl-(2-methylaziridin-1-yl)phosphoryl]-N-prop-2-enylprop-2-en-1-amine Chemical compound CC1CN1P(=O)(N(CC=C)CC=C)N1CC1 LXCIHXPVYQKJAG-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003581 thiophosphoric acid halides Chemical class 0.000 description 1
Description
O — CHO - CH
2 "52 "5
worin R1 Wasserstoff, Chlor oder Brom, R, die Propargyloxycarbonyl- oder Dimethylamidogruppe und R3 Wasserstoff oder die Methylgruppe bedeutet.wherein R 1 is hydrogen, chlorine or bromine, R is the propargyloxycarbonyl or dimethylamido group and R 3 is hydrogen or the methyl group.
2. 2 - (O,O - Diäthylthionophosphoryl) - 5,7 - dimethyl-5-carbäthoxy-pyrazolo-pyrimidin. 2. 2 - (O, O - diethylthionophosphoryl) - 5,7 - dimethyl-5-carbethoxy-pyrazolo-pyrimidine.
3. Verfahren zur Herstellung der Thiophosphorsäureester der Formel gemäß Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise ein Thiophosphorsäurehalogenid der Formel 3. Process for the preparation of the thiophosphoric acid esters of the formula according to Claim 1, characterized in that characterized in that a thiophosphoric acid halide of the formula is used in a manner known per se
C2H5O SC 2 H 5 OS
\T\ T
P—HaiP — shark
C2H5O7 C 2 H 5 O 7
3535
worin Hai für ein Halogenatom steht, mit den entsprechend substituierten 2-Hydroxy-pyrazolopyrimidinen oder deren Alkalisalzen umsetzt.where Hai stands for a halogen atom, with the corresponding substituted 2-hydroxy-pyrazolopyrimidines or their alkali salts.
4. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an einer Verbindung gemäß Anspruch 1.4. Pesticides, characterized in that they contain a compound according to claim 1.
4545
Gegenstand der Erfindung sind die in den Ansprüchen bezeichneten Gegenstände.The subject matter of the invention is the subject matter specified in the claims.
Die neuen Verbindungen gemäß der Erfindung wirken sehr gut gegen phytopathogene Pilze und zeigen außerdem insektizide und akarizide Eigenschaften. The new compounds according to the invention are very effective against phytopathogenic fungi and also show insecticidal and acaricidal properties.
Die neuen Verbindungen können als Wirkstoffe in Schädlingsbekämpfungsmitteln in Mischungen mil den üblichen festen oder flüssigen inerten Trägermaterialien als Stäubemittel oder als Spritzmittel in Form einer wäßrigen Spritzbrühe oder als Emulsion, wenn gewünscht auch zusammen mit anderen Wirkstoffen, angewandt werden.The new compounds can be used as active ingredients in pesticides in mixtures with mil the usual solid or liquid inert carrier materials as dusts or sprays in In the form of an aqueous spray liquor or as an emulsion, if desired also together with other active ingredients, can be applied.
Die Verbindungen zeigen gegenüber bekannten Präparaten eine bessere Wirksamkeit.The compounds are more effective than known preparations.
Folgende, in der Tabelle als I, II, 111, IV bezeichneten Wirkstoffe gemäß der Erfindung wurden gegenüber dem bekannten Vergleichsmittel PFU 26 (Wirkstoff: 2 - Bis - dimethylamido - (3 - amino - 5 - phenyll,2,4-triazolyl)-phosphinoxyd) und einer unbehandelten Kontrollversuchsreihe getestet.The following, designated in the table as I, II, 111, IV Active ingredients according to the invention were compared to the known comparative agent PFU 26 (active ingredient: 2 - bis - dimethylamido - (3 - amino - 5 - phenyll, 2,4-triazolyl) phosphine oxide) and an untreated control series.
1 = 2-(O,O-Diäthylthionophosphoryl)-5,7-di-1 = 2- (O, O-diethylthionophosphoryl) -5,7-di-
methyl-6-carbäthoxy-pyrazoIopyrimidin.
II = 2-(O,O-Diäthylthionophosphoryl)-5-methyl-6-dimethylamido-pyrazolopyrimidin.
methyl-6-carbethoxy-pyrazoIopyrimidine.
II = 2- (O, O-diethylthionophosphoryl) -5-methyl-6-dimethylamido-pyrazolopyrimidine.
III = 2-(0.O-Diäthylthionophosphoryl)-5-methyl - 6 - propargyloxycarbonyl - pyrazolopyrimidin. III = 2- (0.O-diethylthionophosphoryl) -5-methyl - 6 - propargyloxycarbonyl - pyrazolopyrimidine.
IV = 2-(0,0-Diäthylthionophosphoryl)-3-brom-IV = 2- (0,0-diethylthionophosphoryl) -3-bromo-
5 - lneihyi - 6 - propargyioxycarbonyl - puazolopyrimidin. 5 - lneihyi - 6 - propargyioxycarbonyl - puazolopyrimidine.
Gurkenpflanzen einer mehltauempfindlichen Sorte wurden mit einer Konidiensuspension des Gurkenmehltaus (Erysiphe cichoracearum) stark infiziert. 3 Tage nach der Infektion wurden die Gurkenpflanzen mit den oben angeführten Verbindungen, die alle gleichmäßig als 10% Wirkstoff enthaltende emulgierbare Mittel hergestellt waren, behandelt. Die Zusammensetzung der Mittel war folgende:Cucumber plants of a mildew-sensitive variety were treated with a conidia suspension of cucumber powdery mildew (Erysiphe cichoracearum) heavily infected. 3 days after the infection, the cucumber plants became with the compounds listed above, all of which are emulsifiable as 10% active ingredient Means were made, treated. The composition of the funds was as follows:
10,0% Wirkstoff,10.0% active ingredient,
80,0% Äthylalkohol als Lösungsmittel.80.0% ethyl alcohol as a solvent.
10,0% Nonylphenol mit 10 AeO als Emulgator.10.0% nonylphenol with 10 AeO as an emulsifier.
Das so hergestellte emulgierbare Konzentrat wurde mit so viel Wasser emulgiert, daß die Anwendungskonzentration jeweils 200, 100, 50, 25, 10 und 5 mg Wirkstoffe Liter Spritzbrühe betrugen. Als Vergleichsmittel diente eine mehltauwirksame, handelsübliche Phosphorsäureverbindung, PFU 26, die in den gleichen Anwendungskonzentrationen und unter gleichen Anwendungsbedingungen gespritzt wurde, sowie eine unbehandelte Kontrolle. Die Versuche wurden in 4facher Wiederholung durchgeführt.The emulsifiable concentrate prepared in this way was emulsified with so much water that the application concentration was 200, 100, 50, 25, 10 and 5 mg in each case Active ingredients liters of spray liquid. A powdery mildew-effective, commercially available agent was used as a comparison agent Phosphoric acid compound, PFU 26, in the same use concentrations and under the same Application conditions was sprayed, as well as an untreated control. The attempts were made in Repeated 4 times.
Das Ergebnis der Auswertung dieser Versuche 3 Wochen nach der Behandlung zeigt die Tabelle. Die Mittel gemäß der Erfindung zeigen eine dem Vergleichsmittel weit überlegene Wirkung.The result of the evaluation of these tests 3 weeks after the treatment is shown in the table. The agents according to the invention show an effect that is far superior to the comparison agent.
Präparat Mehltaubefall in % nach Anwendung von mg Wirkstoff je Liter SpritzbrühcPreparation powdery mildew infestation in% after application of mg of active ingredient per liter of spray mixture
200 mg/1 100 mg/1 50mgl 25 mg/1200 mg / 1 100 mg / 1 50 mg / 1 25 mg / 1
10 mg,-110 mg, -1
5 mg, I5 mg, I.
Beispiel 1 Oexample 1 O
HC=C-CI-U-O-CHC = C-CI-U-O-C
0-P(OC2H5), ίο0-P (OC 2 H 5 ), ίο
Ein Gemisch aus 23 g(O,l Mol)2-Hydroxy-5-methyl-6 - propargyloxycarbonyl - pyrazolo - pyrimidin, 19 g (0,1 Mol) Diäthylthiophosphorylchlorid, 12 g (0,12MoI) Triäthylamin und 250 ml Benzol wird IO Stunden lang bei 50'C gerührt. Danach wird das Triäthylaminhydrochlorid mit Wasser ausgewaschen und das Benzol abdestilliert.A mixture of 23 g (0.1 mol) of 2-hydroxy-5-methyl-6-propargyloxycarbonyl-pyrazolo-pyrimidine, 19 g (0.1 mol) diethylthiophosphoryl chloride, 12 g (0.12 mol) triethylamine and 250 ml benzene Stirred for 10 hours at 50.degree. The triethylamine hydrochloride is then washed out with water and the benzene is distilled off.
Als Rückstand hinterbleibt 2-(O,O-Diäthylthionophosphoryl) - 5 - methyl - 6 - propargyloxycarbonylpyrazolo-pyrimidin als helles öl.The residue is 2- (O, O-diethylthionophosphoryl) - 5 - methyl - 6 - propargyloxycarbonylpyrazolo-pyrimidine as a light oil.
Ausbeute 34 g.Yield 34g.
Analyse (Molgewicht 383):Analysis (molecular weight 383):
Berechnet... P 8,1, N 11,0%;Calculated ... P 8.1, N 11.0%;
nefunden .... P 7,8, N 11,2%.found .... P 7.8, N 11.2%.
(CH3)2NC(CH 3 ) 2 NC
0-P(OC2Hj)2 0-P (OC 2 Hj) 2
34,2 g (0,15 Mol) Natriumsalz des 2-Hydroxy-5-methyl-6-dimethylamido-pyrazolo-pyrimidin werden in 250 ml Methyläthylketon suspendiert und mit 28,4 g (0,15MoI) Diätiiylthiophosphorsäurechlorid versetzt und 8 Stunden lang unter Rückfluß erhitzt. Aus dem vom NaCl befreiten Filtrat erhält man 54 g 2- (O,O - Diäthylthionophosphory!)- 5- methyl - 6 -dimethylamido-pyrazolo-pyrimidin als rotbraunes öl. welches erstarrt.34.2 g (0.15 mol) of the sodium salt of 2-hydroxy-5-methyl-6-dimethylamido-pyrazolo-pyrimidine are suspended in 250 ml of methyl ethyl ketone and treated with 28.4 g (0.15 mol) of diethylthiophosphoric acid chloride and refluxed for 8 hours. 54 g are obtained from the filtrate from which the NaCl has been removed 2- (O, O-diethylthionophosphory!) -5-methyl-6-dimethylamido-pyrazolo-pyrimidine as a red-brown oil. which freezes.
Analyse (Molgewicht 372):Analysis (molecular weight 372):
Berechnet ... P 8,3, N 15,1%;
gefunden .... P 7,9, N 15,2%.Calculated ... P 8.3, N 15.1%;
found .... P 7.9, N 15.2%.
Beispiel 2 OExample 2 O
HCsC-CH2-O-CHCsC-CH 2 -OC
3535
22 g (0,07 Mol) 2 - Hydroxy - 3 - brom - 5 - methyl-6-propargyloxycarbonyl-pyrazolo-pyrimidin werden in 250 ml Aceton gelöst, 9 g (0,09 Mol) Triäthylamin zugegeben und 13,5 g (0,07 Mol) Ο,Ο-Diäthylthionophosphorsäurechlorid zugetropft. Nach 5stündigem Kochen unter Rückfluß wird vom ausgefallenen Triäthylaminhydrochlorid abfiltriert. Aus der organischen Phase erhält man 26 g 2-(O,O-Diäthylthionophosphoryl) - 3 - brom - 5 - methyl - 6 - propargyloxycarbonyl - pyrazolo - pyrimidin ais langsam erstarrendes öl.22 g (0.07 mol) of 2-hydroxy-3-bromo-5-methyl-6-propargyloxycarbonyl-pyrazolo-pyrimidine are dissolved in 250 ml of acetone, 9 g (0.09 mol) of triethylamine are added and 13.5 g ( 0.07 mol) Ο, Ο-diethylthionophosphoric acid chloride was added dropwise. After refluxing for 5 hours, the precipitated triethylamine hydrochloride is filtered off. 26 g of 2- (O, O-diethylthionophosphoryl) -3-bromo-5-methyl-6-propargyloxycarbonyl-pyrazolo-pyrimidine are obtained as a slowly solidifying oil from the organic phase.
Analyse (Molgewicht 462):
Berechnet ... P 6,7, N 9,1%: gefunden .... P 6,9, N 8,9%.Analysis (molecular weight 462):
Calculated ... P 6.7, N 9.1%: found .... P 6.9, N 8.9%.
C2H5OCC 2 H 5 OC
O — P(OC2H5I2 O - P (OC 2 H 5 I 2
23,5g (0,1 Mol) 2-Hydroxy-5,7-dimethyl-6-carbäthoxy-pyrazolo-pyrimidin werden in 250 ml Benzol gelöst und mit 11 g (0,11 Mol) Triäthylamin und 19 g (0,1 Mol) O^-Diäthylthionophosphorsäurechlorid unter Rühren 15 Stunden lang auf 60° C erhitzt. Nach Filtrieren und Abdestillieren des Lösungsmittels erhält man 37 g 2-(O,O-Diäthylthionophosphoryl)-5,7-dimethyl-6-carbäthoxy-pyrazolo-pyrimidin als langsam erstarrendes öl.23.5 g (0.1 mol) of 2-hydroxy-5,7-dimethyl-6-carbethoxy-pyrazolo-pyrimidine are dissolved in 250 ml of benzene and mixed with 11 g (0.11 mol) of triethylamine and 19 g (0.1 mol) O ^ -diethylthionophosphoric acid chloride heated to 60 ° C. for 15 hours with stirring. After filtering and distilling off the solvent is obtained 37 g of 2- (O, O-diethylthionophosphoryl) -5,7-dimethyl-6-carbethoxy-pyrazolo-pyrimidine as a slowly solidifying oil.
Analyse (Molgewicht 387):Analysis (molecular weight 387):
Berechnet ... P 8,0, N 10,8%;
gefunden .... P 7,9, N 10,4%.Calculated ... P 8.0, N 10.8%;
found .... P 7.9, N 10.4%.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052467 | 1967-05-20 | ||
| DEF0052467 | 1967-05-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1642260A1 DE1642260A1 (en) | 1971-12-02 |
| DE1642260B2 DE1642260B2 (en) | 1975-07-31 |
| DE1642260C3 true DE1642260C3 (en) | 1976-03-11 |
Family
ID=
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