DE1950492C3 - 2,4-Dioxo-l 3-benzoxazinothionophosphonic acid ester, process for their preparation and their use - Google Patents
2,4-Dioxo-l 3-benzoxazinothionophosphonic acid ester, process for their preparation and their useInfo
- Publication number
- DE1950492C3 DE1950492C3 DE19691950492 DE1950492A DE1950492C3 DE 1950492 C3 DE1950492 C3 DE 1950492C3 DE 19691950492 DE19691950492 DE 19691950492 DE 1950492 A DE1950492 A DE 1950492A DE 1950492 C3 DE1950492 C3 DE 1950492C3
- Authority
- DE
- Germany
- Prior art keywords
- dioxo
- acid ester
- preparation
- methyl
- benzoxazinothionophosphonic
- 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
- 239000002253 acid Substances 0.000 title claims description 16
- 150000002148 esters Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- -1 ester halides Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000749 insecticidal Effects 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PVEQZIQAQALJSB-UHFFFAOYSA-N 3-hydroxy-1,3-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)OC2=C1 PVEQZIQAQALJSB-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 230000000895 acaricidal Effects 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- HOJNRTMRUQQXMX-UHFFFAOYSA-N COCCP(O)(O)=S Chemical compound COCCP(O)(O)=S HOJNRTMRUQQXMX-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N Dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229940050176 Methyl Chloride Drugs 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N Methyl isopropyl ketone Chemical group CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal Effects 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
N-OHN-OH
in Form seiner Alkali-, Erdalkali- bzw. Ammoniumsalze oder in Gegenwart von Säurebindemitteln mit Alkan-O-alkyl-thionophosphonsäureesterhalogeniden der Formel IIIin the form of its alkali, alkaline earth or ammonium salts or in the presence of acid binders Alkane-O-alkyl-thionophosphonic acid ester halides of formula III
S ORS OR
II/II /
Hal—PHal-P
\
Ri \
Ri
in welcherin which
Hai für ein Halogenatom steht, umsetztHai stands for a halogen atom
3. Verwendung von Verbindungen gemäß Anspruch 1 zur Bekämpfung von Insekten und Milben.3. Use of compounds according to Claim 1 for combating insects and mites.
Aus der NL-OS 67 04 838 ist bereits bekannt, daß 2,4-Dioxo-13-bcnzoxazino-thiono-phosphorsäureester, z. B. der 0,0-Dimethyl-O-[2,4-dioxo-benzoxazin-(3)-yi]-thionophosphoriäureester, insektizide und herbizide Eigenschaften aufweisen.From NL-OS 67 04 838 it is already known that 2,4-dioxo-13-benzoxazino-thionophosphoric acid ester, z. B. the 0,0-dimethyl-O- [2,4-dioxo-benzoxazin- (3) -yi] -thionophosphoric acid ester, have insecticidal and herbicidal properties.
Die vorliegende Erfindung betrifft nun die im Anspruch definierten 2,4-Dioxo-l,3-benzoxazino-thionopliGsphonsäureester, welche insektizide und akarizide Eigenschaften haben, sowie ein Verfahren zu ihrer Herstellung sowie ihre Verwendung.The present invention relates to the 2,4-dioxo-1,3-benzoxazino-thionophosphonic acid esters defined in the claim, which have insecticidal and acaricidal properties and a method for their Manufacture and their use.
Überraschenderweise zeichnen sich die erfindungsgemäßen 2,4- Dioxo-1,3-benzoxazino-thionophosphonsäureester (I) durch eine erheblich bessere insektizide und akarizide Wirkung als die bekannten 2,4-Dioxo-1,3-benzoxazino-thionophosphorsäureester analoger Konstitution und gleicher Wirkungsart aus. Die erfindungsgemäßen Stoffe stellen somit eine echte Bereicherung der Technik dar.Surprisingly, the 2,4-dioxo-1,3-benzoxazino-thionophosphonic acid esters according to the invention are notable (I) by a considerably better insecticidal and acaricidal effect than the known ones 2,4-Dioxo-1,3-benzoxazino-thionophosphoric acid ester analogous constitution and the same type of effect. The substances according to the invention thus represent a real one Enrichment of technology.
Verwendet man beispielsweise 3-Hydroxy-2,4-dioxo-1,3-benzoxazin und Methan-O-methyl-thionophosphonsäureesterchlorid als Ausgangsmaterialien, so kann der Reaktionsablauf durch das folgende Formelschem? wiedergegeben werden:For example, 3-hydroxy-2,4-dioxo-1,3-benzoxazine is used and methane-O-methyl-thionophosphonic acid ester chloride as starting materials, so can the course of the reaction through the following equation? be reproduced:
S OCH,S OCH,
CH3 CH 3
Vorzugsweise stehen R und Ri für Methyl oder Äthyl und Hai für ein Chloratom.Preferably R and Ri are methyl or ethyl and Hal is a chlorine atom.
Als Beispiele für verwendbare Thionophosphonsäureesterhalogenide seien im einzelnen genannt:Examples of thionophosphonic acid ester halides that can be used are:
Methan-O-methyl-, Methan-O-äthyl-, Äthan-O-äthyl-,
Äthan-O-methyl-.Methan-Q-isopropyl-,
Isopropan-O-isopropyl-, Isopropan-O-methyl- und
Isopropan-O-äthyl-thionophosphonsäureesterchlorid.
Die als Ausgangsstoffe zu verwendenden Thionophosphonsäureesterhalogenide
(III) und das 3-Hydroxy-2,4-dioxo-benzoxazin sind in der Literatur beschrieben und können nach bekannten Methoden hergestellt
werden.Methane-O-methyl-, methane-O-ethyl-, ethane-O-ethyl-,
Ethane-O-methyl-.Methane-Q-isopropyl-,
Isopropane-O-isopropyl-, isopropane-O-methyl- and
Isopropane-O-ethyl-thionophosphonic acid ester chloride.
The thionophosphonic ester halides (III) and 3-hydroxy-2,4-dioxobenzoxazine to be used as starting materials are described in the literature and can be prepared by known methods.
Als Solventien kommen bei Durchführung des Verfahrens alle inerten organischen Lösungs- bzw.
Verdünnungsmittel in Frage. Hierzu gehören aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasserstoffe,
wie Benzol, Toluol, Xylol, Benzin, Methylchlorid, Chloroform, Tetrachlorkohlenstoff
Chlorbenzol, Äther, z.B. Diäthyl- und Dibutyläther, Dioxan, ferner Ketone, wie Aceton, Methyläthyl-,
Methylisopropyl- und Methylisobutylketon, außerdem Nitrile, beispielsweise Acetonitril.
Als Säureakzeptoren kommen alle üblichen Säurebindemittel
in Frage. Als besonders geeignet erwiesen sich Alkalicarbonate und -alkoholate, wie Natrium- und
Kaliumcarbonat, -methylat bzw. -äthylat, ferner aliphatische,
aromatische oder heterocyclische Amine, beispielsweise Triäthylamin, Dimethylamin, Dimethylani-Hn,
Dimethylbenzylamin und Pyridin.All inert organic solvents or diluents can be used as solvents when carrying out the process. These include aliphatic and aromatic, optionally chlorinated hydrocarbons such as benzene, toluene, xylene, gasoline, methyl chloride, chloroform, carbon tetrachloride, chlorobenzene, ethers, e.g. diethyl and dibutyl ethers, dioxane, and ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, also nitriles, for example acetonitrile.
All customary acid binders can be used as acid acceptors. Alkali metal carbonates and alcoholates, such as sodium and potassium carbonate, methylate or ethylate, and also aliphatic, aromatic or heterocyclic amines, for example triethylamine, dimethylamine, dimethylani-Hn, dimethylbenzylamine and pyridine, have proven particularly suitable.
Die Reaktionstemperaturen können in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man zwischen —10 und 600C, vorzugsweise bei 0 bis 300C.The reaction temperatures can be varied over a wide range. In general, work is carried out between -10 and 60 ° C., preferably at 0 to 30 ° C.
Die Umsetzung läuft gewöhnlich bei Normaldruck ab. Zur Durchführung des Verfahrens werden die Ausgangsstoffe meist in äquimolarem Verhältnis eingesetzt Ein Überschuß der einen oder anderen Reaktionskomponente bringt keine wesentlichen Vorteile. Die Umsetzung wird in einem geeigneten Lösungsmittel in Anwesenheit eines Säureakzeptors vorgenommen und das Reaktionsgemisch einige Stunden nachgerührt Anschließend gießt man die Mischung in angesäuertes Wasser und arbeitet sie wie Üblich auf.The reaction usually takes place at normal pressure. To carry out the procedure, the Starting materials are usually used in an equimolar ratio. An excess of one or the other reaction component has no significant advantages. the The reaction is carried out in a suitable solvent in the presence of an acid acceptor and the reaction mixture is stirred for a few hours. The mixture is then poured into acidified Water and processes it as usual.
Die erfindungsgemäßen Produkte zeichnen sich durch eine hervorragende insektizide und aksrizide Wirkung bei nur geringer Phytotoxizität aus. Die pestizide Wirkung setzt dabei schnell ein und hält langeThe products according to the invention are characterized by an excellent insecticidal and aksricidal properties Effect with only low phytotoxicity. The pesticidal effect sets in quickly and lasts for a long time
an. Aufgrund dieser Eigenschaften finden die neuen Stoffe im Pflanzen- und Vorratsschutz sowie auf dem Hygienesektor zur Bekämpfung von schädlichen saugenden und beißenden Insekten sowie von Milben Verwendung.on. Because of these properties, the new substances are used in plant and stored product protection as well as on the Hygiene sector for the control of harmful sucking and biting insects as well as mites Use.
Die Formulierungen enthalten im allgei; en zwischen 0,1 und 95 Gewichtsprozent Wirksto,., vorzugsweise zwischen 0,5 und 90%.The formulations generally contain; s between 0.1 and 95 percent by weight active ingredient,., preferably between 0.5 and 90%.
Die Wirkstoffkonzentrationen können in einem größeren Bereich variiert werden. Im allgemeinen verwendet man Konzentrationen von 0,0005 bis 20%, vorzugsweise von 0,005 bis 5%.The active ingredient concentrations can be varied over a wide range. In general concentrations of 0.0005 to 20%, preferably 0.005 to 5%, are used.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder der daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, emulgierbare Konzentrate, Emulsionen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden.The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, Pastes, soluble powders, dusts and granules can be applied.
Zu einer Lösung von 106 g (0,6 Mol) 3-Hydroxy-l,3-benzoxazin-2,4-dion (Fp. 235-2360C) in 200 ml Pyridin tropft man unter Eiskühlung bei einer 300C nicht übersteigenden Temperatur 95 g (0,6 Mol) Methan-O-äthyl-thionophosphonsäureesterchlorid und gießt die Mischung nach einstündigem Rühren in mit Salzsäure angesäuertes Wasser. Das dabei ölig ausfallende Produkt erstarrt bald kristallia Man saugt die Kristalle ab und wäscht sie neutral. Die Rohausbeute an Methan-0-äthyl-0-[2,4-dioxo-1,3-benzoxazino-(3)-y I]-thionophosphonsäureester beträgt 155 g (86% der Theorie). Aus Äthanol (1 g/3 ml) erhält man farblose Kristalle vom Fp. 11 TC.To a solution of 106 g (0.6 mol) of 3-hydroxy-l, 3-benzoxazin-2,4-dione (mp. 235-236 0 C) in 200 ml of pyridine under ice-cooling does not drip at a 30 0 C temperature exceeding 95 g (0.6 mol) of methane-O-ethyl-thionophosphonic acid ester chloride and, after stirring for one hour, pour the mixture into water acidified with hydrochloric acid. The oily product which precipitates out soon solidifies as crystals. The crystals are filtered off with suction and washed neutral. The crude yield of methane-0-ethyl-0- [2,4-dioxo-1,3-benzoxazino- (3) -y I] -thionophosphonic acid ester is 155 g (86% of theory). Colorless crystals with a melting point of 11 TC are obtained from ethanol (1 g / 3 ml).
Für C,, Hi2NO5PS (Molgewicht 301,3):For C ,, Hi 2 NO 5 PS (molecular weight 301.3):
OCH,OCH,
99 g (0,55 Mol) 3-Hydroxy-l,3-benzoxazin-2,4-dion (hergestellt nach USA-Patentschrift 2714105; Fp. 235-236°C) werden in 20 ml Pyridin gelöst Unter Kühlung mit Eiswasser tropft man zu dieser Lösung 73 g (0,5 Mol) Methyl-O-methyl-thionophosphonsäureesterchlorid mit solcher Geschwindigkeit zu, daß eine \$ Innentemperatur von 300C nicht überstiegen wird, und gießt die Mischung nach einstündigem Rühren in mit Salzsäure angesäuertes Wasser. Das zunächst ausfallende öl erstarrt sehr bald kristallin. Man saugt die Kristalle ab und wäscht sie säurefrei Die Rohausbeute an Methan-O-methyl-O-{2,4-dioxo-1,3-benzoxazino-(3)-yi]-thionophosphonsäureester beträgt 80 g (55% der Theorie). Durch Umkristallisieren aus Äthanol (1 g/ 5 ml) erhält man das Produkt in Form farbloser Kristalle vomFp.l41eC99 g (0.55 mol) of 3-hydroxy-1,3-benzoxazine-2,4-dione (prepared according to USA patent specification 2714105; melting point 235-236 ° C.) are dissolved in 20 ml of pyridine, while cooling with ice water to this solution 73 g (0.5 mol) of methyl O-methyl-thionophosphonsäureesterchlorid with such speed that a \ $ internal temperature of 30 0 C is not exceeded, and pouring the mixture after stirring into acidified with hydrochloric acid water. The initially precipitated oil soon solidifies in crystalline form. The crystals are suctioned off and washed acid-free. The crude yield of methane-O-methyl-O- {2,4-dioxo-1,3-benzoxazino- (3) -yi] -thionophosphonic acid ester is 80 g (55% of theory) . (G of 1/5 ml) by recrystallization from ethanol is obtained the product in form of colorless crystals vomFp.l41 e C
Für C10H10NO5PS (Molgewicht 287,2):For C10H10NO5PS (molecular weight 287.2):
Berechnet: N 4,87, P 11,17, S 1031%;
gefunden: N 431, P 11,23, S 1037%.Calculated: N 4.87, P 11.17, S 1031%;
found: N 431, P 11.23, S 1037%.
Berechnet: N 4,64, P !0,64, S 3; gefunden: N 4,70, P 10,81, S 10,47%.Calculated: N 4.64, P! 0.64, S 3; found: N 4.70, P 10.81, S 10.47%.
In analoger Weise wie oben beschrieben wird die Verbindung folgender Struktur hergestellt:In a manner analogous to that described above, the connection with the following structure is established:
40 OC2H5 40 OC 2 H 5
Die Rohausbeute an Äthan-O-äthyl-O-[2,4-dioxo-l,3-benzoxazino-(3)-yl]-thionophosphonsäureester beträgt 176 g (93% der Theorie). Durch Umkristallisieren aus Äthanol (1 g/3 ml) wird das Produkt in Form farbloser, derber Kristalle vom Fp. 1000C erhalten.The crude yield of ethane-O-ethyl-O- [2,4-dioxo-1,3-benzoxazino- (3) -yl] -thionophosphonic acid ester is 176 g (93% of theory). The product is obtained in the form of colorless, coarse crystals with a melting point of 100 ° C. by recrystallizing from ethanol (1 g / 3 ml).
Für Ci2Hi4NO5PS (Molgewicht 315,3):For Ci 2 Hi 4 NO 5 PS (molecular weight 315.3):
Berechnet: N 4,44, P 10,17, S 9,82%; gefunden: N 4,59, P 10,25, S 10,17%.Calculated: N 4.44, P 10.17, S 9.82%; found: N 4.59, P 10.25, S 10.17%.
Claims (2)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE757187D BE757187A (en) | 1969-10-07 | NEW ESTERS OF 2,4-DIOXO-1,3-BENZOXAZINOTHIONOPHOSPHONIC ACID, THEIR PREPARATION PROCESS AND THEIR PREPARATION AS INSECTICIDES AND ACARICIDES | |
| DE19691950492 DE1950492C3 (en) | 1969-10-07 | 2,4-Dioxo-l 3-benzoxazinothionophosphonic acid ester, process for their preparation and their use | |
| IL35309A IL35309A (en) | 1969-10-07 | 1970-09-17 | 2,4-dioxo-1,3-benzoxazinothiono-phosphonic acid esters,process for their preparation and their use as insecticides and acaricides |
| ZA706381A ZA706381B (en) | 1969-10-07 | 1970-09-18 | 2,4-dioxo-1, 3-benzoxazinothionophosphonic acid esters,process for their preparation,and their use as insecticides and acaricides |
| CH1409770A CH528546A (en) | 1969-10-07 | 1970-09-23 | Process for the preparation of 2,4-dioxo-1,3-benzoxazino-thionophosphonic acid esters |
| US00074856A US3717631A (en) | 1969-10-07 | 1970-09-23 | 2,4'dioxo-1,3-benzoxazinothionophosphonic acid esters |
| GB47012/70A GB1267288A (en) | 1969-10-07 | 1970-10-02 | 2,4-dioxo-2,3- dihydro-4h-1,3-benzoxazinothiono-phosphonic acid esters, process for their preparation, and their use as insecticides and acaricides |
| JP45086726A JPS4916943B1 (en) | 1969-10-07 | 1970-10-05 | |
| TR16617A TR16617A (en) | 1969-10-07 | 1970-10-05 | 2,4-DIOXO-1,3-BENZOXAZINOTHIONOPHOSPHONIC ACID ESTERS |
| NL7014599A NL7014599A (en) | 1969-10-07 | 1970-10-05 | |
| JP45086725A JPS502990B1 (en) | 1969-10-07 | 1970-10-05 | |
| IT30650/70A IT968018B (en) | 1969-10-07 | 1970-10-06 | ESTERS OF ACID 2 4 DIOX 1 3 BENZOSSAZIN TION PHOSPHONIC PROCE DIMENTO FOR THEIR PREPARATION AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| ES384280A ES384280A1 (en) | 1969-10-07 | 1970-10-06 | 2,4'dioxo-1,3-benzoxazinothionophosphonic acid esters |
| PL1970143794A PL69658B1 (en) | 1969-10-07 | 1970-10-06 | |
| FR7036284A FR2065156A5 (en) | 1969-10-07 | 1970-10-07 | |
| AT902670A AT297031B (en) | 1969-10-07 | 1970-10-07 | Process for the preparation of new 2,4-dioxo-1,3-benzoxazino-thionophosphonic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691950492 DE1950492C3 (en) | 1969-10-07 | 2,4-Dioxo-l 3-benzoxazinothionophosphonic acid ester, process for their preparation and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1950492A1 DE1950492A1 (en) | 1971-04-29 |
| DE1950492B2 DE1950492B2 (en) | 1977-04-07 |
| DE1950492C3 true DE1950492C3 (en) | 1977-11-24 |
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