DE1643706C - Thinonophosphon (or) acid esters - Google Patents
Thinonophosphon (or) acid estersInfo
- Publication number
- DE1643706C DE1643706C DE1643706C DE 1643706 C DE1643706 C DE 1643706C DE 1643706 C DE1643706 C DE 1643706C
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- acid ester
- methylsulfinylphenyl
- acid esters
- thinonophosphon
- 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 8
- 150000002148 esters Chemical class 0.000 title claims description 7
- -1 methoxy, ethoxy Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UERPKMLSSINZIO-UHFFFAOYSA-M ClC1=C(C=C(C(=C1)S(=O)C)Cl)[O-].[Na+] Chemical compound ClC1=C(C=C(C(=C1)S(=O)C)Cl)[O-].[Na+] UERPKMLSSINZIO-UHFFFAOYSA-M 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 240000001307 Myosotis scorpioides Species 0.000 description 2
- 230000000895 acaricidal Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000000749 insecticidal Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- YGFPFLRARVYKBZ-UHFFFAOYSA-N 2,5-dichloro-4-methylsulfanylphenol Chemical compound CSC1=CC(Cl)=C(O)C=C1Cl YGFPFLRARVYKBZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 240000005158 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- SHHNZMWZZCIDHE-UHFFFAOYSA-M [Cl-].CCOP(O)(=S)C1=CC=CC=C1 Chemical compound [Cl-].CCOP(O)(=S)C1=CC=CC=C1 SHHNZMWZZCIDHE-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- LMPILSLHAQVENA-UHFFFAOYSA-N dihydroxy-(2-methylpropoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)COP(O)(O)=S LMPILSLHAQVENA-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 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
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Description
Die Erfindung betrifft Thionophosphon(or)säurccsler der allgemeinen FormelThe invention relates to thionophosphonic acids the general formula
R1OR 1 O
SO --: CHjSO -: CHj
SOCH, + KtZSOCH, + KtZ
IOIO
in der R, einen Alkylrest mit I bis 3 C-Atomen, R2 den Methyl-, Äthyl-, Methoxy-, Äthoxy- oder Phenylrest bedeutet.in which R, an alkyl radical with 1 to 3 carbon atoms, R 2 denotes the methyl, ethyl, methoxy, ethoxy or phenyl radical.
Die erfindungsgemäßen .Verbindungen werden hergestellt, indem man gemäß dem ReaktionsschemaThe compounds according to the invention are produced by following the reaction scheme
(Z = Halogenatom, Kt = einwertiges Kation oder ein Äquivalent eines mehrwertigen Kations) ein entsprechenden Thiophosphor- bzw. Thiophosphonsäurehalogenid mit einem geeigneten Phenolsalz umsetzt. Die Umsetzung erfolgt in einem organischen Lösungsmittel, beispielsweise einem Keton, Toluol, Dioxar., oder in wäßriger Lösung, gegebenenfalls bei erhöhter Temperatur. In den Ausgangsstoffen bedeutet Z vorzugsweise ein Chloratom, während als Phenolsalze insbesondere die Alkali- und Ammoniumsalze in Frage kommen.(Z = halogen atom, Kt = monovalent cation or an equivalent of a polyvalent cation) corresponding thiophosphorus or thiophosphonic acid halide is reacted with a suitable phenol salt. The reaction takes place in an organic solvent, for example a ketone, toluene, Dioxar., Or in aqueous solution, optionally at elevated temperature. In the raw materials Z preferably denotes a chlorine atom, while the phenol salts are in particular the alkali metal and ammonium salts come into question.
Die nach dem Verfahren der Erfindung hergestellten Verbindungen sind dünnschichtchromatographisch einheitlich. Als Laufmittel wurde ein Gemisch aus Hexan und Aceton 2:1 verwendet, entwickelt wurde mit 3%iger Palladiumchloridlösung.The compounds prepared by the process of the invention are thin layer chromatography uniformly. A mixture of hexane and acetone 2: 1 was used as the mobile phase and was developed with 3% palladium chloride solution.
Die als Ausgangsstoffe verwendeten Phenole können hergestellt werden, indem man die entsprechenden l.Z^-Trichlor-^methylmercapto-Verbindungen mit wäßrigmethanolischem Natriumhydroxid im Autoklav bei erhöhter Temperatur zum 2,5-Dichlor-4-methylmercaptophenol umsetzt und anschließend mit Wasserstoffperoxid in Eisessig zum Sulfoxid oxydiert.The phenols used as starting materials can be prepared by adding the appropriate l.Z ^ -Trichlor- ^ methylmercapto compounds with aqueous methanolic sodium hydroxide in the autoclave at elevated temperature to 2,5-dichloro-4-methylmercaptophenol and then oxidized to sulfoxide with hydrogen peroxide in glacial acetic acid.
Die erfindungsgemäßen Verbindungen sind stark wirksame Insektizide und Akarizide. Für die Anwendung werden sie in üblicher Weise mit inerten Hilfsund Trägerstoffen, z. B. zu Emulsionen, Stäubemitteln, Streupulvern, formuliert. Die Anwendungskonzentrationen betragen etwa 0,01 bis 5%.The compounds of the invention are highly effective insecticides and acaricides. For the application they are in the usual way with inert auxiliaries and carriers such. B. on emulsions, dusts, Scatter powders, formulated. The use concentrations are about 0.01 to 5%.
Die überlegene Wirksamkeit der erfindungsgemäßen Verbindungen gegenüber dem als Insektizid und Akarizid bewährten Handelsprodukt Ο,Ο-Dimcthyl-O-(4-methylmercapto-3-methylphenyl)-thionophos- phat (A) zeigt sich in den folgenden Vergleichen. Darin wurden die folgenden erfindungsgemäßen Verbindungen untersucht:The superior effectiveness of the compounds according to the invention compared to that as an insecticide and Acaricide proven commercial product Ο, Ο-Dimethyl-O- (4-methylmercapto-3-methylphenyl) -thionophos- phat (A) is shown in the following comparisons. Therein were the following compounds of the invention examined:
B. 0,0-DiHthyl-0-(2,5-dichIor-4-methylsulfinylphenyO-thionophosphorsHureester; B. 0,0-diethyl-0- (2,5-dichloro-4-methylsulfinylphenyO-thionophosphoric acid ester;
C. 0-Äthy!-0-(2,5-dichlor-4-mcthylsulfinylphenyl)-methyl-thionophosphonsUureesler; C. O-Ethy! -0- (2,5-dichloro-4-methylsulfinylphenyl) -methyl-thionophosphonic acid ester;
D. O,O-Dimethyl-O-(2,5-dichlor-4-methylsuirinylphenyO-thionophosphorsäurecster; D. O, O-Dimethyl-O- (2,5-dichloro-4-methylsuirinylphenyO-thionophosphoric acid ester;
E. O - Methyl - O - (2,5 ■ dichlor - 4 - methylsulfinylphenyl)-methylthionophosphonsiiureester; E. O - methyl - O - (2,5 ■ dichloro - 4 - methylsulfinylphenyl) methylthionophosphonic acid ester;
F. 0-n-Propyl-0-(2,5-dichlor-4-methylsulfinylphenyl)-methylthionophosphonsiiureester; F. 0-n-Propyl-0- (2,5-dichloro-4-methylsulfinylphenyl) -methylthionophosphonic acid ester;
G. O-Äthyl- O-(2,5-dichlor-4-methylsulfinylphenyl)-phenylthionophosphonsäureester. G. O-Ethyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -phenylthionophosphonic acid ester.
I. Bekämpfung von Blattläusen auf Bohnen,I. Control of aphids on beans,
Freilandversuch, wäßrige Emulsion der WirkstoffeField experiment, aqueous emulsion of the active ingredients
B
CA.
B.
C.
0,01
0,010.02
0.01
0.01
100
10095
100
100
II. Gespinstmottenraupen, Freilandversuch, wäßrige Emulsion der WirkstoffeII. Spider moth caterpillars, field test, aqueous emulsion of the active ingredients
B
CA.
B.
C.
0,02
0,020.02
0.02
0.02
100
10085
100
100
III. Abtötung von Blattläusen im Gewächshausversuch, Auswertung nach 1 Stunde, wäßrige Emulsion der WirkstoffeIII. Killing of aphids in the greenhouse experiment, evaluation after 1 hour, aqueous emulsion of the active ingredients
WirkstoffActive ingredient
Abtötung in % bei einer Wirkstoffkonzentration von 0,0002% 0,0006% 0,001%Killing in% at an active ingredient concentration of 0.0002% 0.0006% 0.001%
1010
7070
30
9030th
90
80 10080 100
IV. Wirkung gegen StubenfliegenIV. Effect against house flies
V. Wirkung gegen Raupen (Plutella maculipennis)V. Effect against caterpillars (Plutella maculipennis)
GA.
G
0,0003%0.003%
0.0003%
Die Herstellung der erfindungsgcmiißen Wirkstoffe ist nachstehend näher erläutert.The production of the active ingredients according to the invention is explained in more detail below.
B e i s ρ i e I 1B e i s ρ i e I 1
a) O.O-Diäthyl-O-i^S-dichloM-methylsulfinyl-a) O.O-diethyl-O-i ^ S-dichloM-methylsulfinyl-
phenyl)-thionophosphorsäureesterphenyl) thionophosphoric acid ester
(Molgewicht 377,26)(Molecular weight 377.26)
24,7 g (0,1 Mol) Natrium-^S-dichloM-methylsulfinylphenolat, (Schmelzpunkt des Phenols 2100C) werden in 70 ml Methyl-isobutylkeion mit 20,8 g (0,11 Mol) Ο,Ο-Diäthylthionophosphorsäurechloricf Stunden bei 800C gerührt. Das Lösungsmittel wird dann abdestilliert, der Rückstand in Methylenchlorid gelöst, mit Wasser, dann 2 n-Natronlauge, dann wiederum Wasser ausgeschüttelt und über Natriumsulfat getrocknet. Man destilliert das Methylenchlorid ab und erhitzt den Rückstand V2 Stunde auf dem siedenden Wasserbad im ölpumpenvakuum.24.7 g (0.1 mol) of sodium ^ S-dichloM-methylsulfinylphenolat, (melting point of the phenol 210 0 C) in 70 ml of methyl isobutylkeion with 20.8 g (0.11 mol) Ο, Ο-Diäthylthionophosphorsäurechloricf Stirred at 80 ° C. for hours. The solvent is then distilled off, the residue is dissolved in methylene chloride, extracted with water, then 2N sodium hydroxide solution, then water again and dried over sodium sulfate. The methylene chloride is distilled off and the residue V is heated for 2 hours on a boiling water bath in an oil pump vacuum.
Ausbeute: 35,7 g (95% der Theorie), F. 58 bis 59°C. Analyse:Yield: 35.7 g (95% of theory), mp 58 to 59 ° C. Analysis:
Berechnet ... P 8,22, S 17,03, Cl 18,81%; gefunden .... P 8,14, S 16,94, Cl 19,00%.Calculated ... P 8.22, S 17.03, Cl 18.81%; found .... P 8.14, S 16.94, Cl 19.00%.
Analog dem Beispiel 1 a wurden folgende Verbindungen hergestellt:The following compounds were produced analogously to Example 1 a:
b) O,O-Dimethyl-O-(2,5-dichlor-4-methylsulfinylphenyl)-thionophosphorsäureester ausb) O, O-Dimethyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -thionophosphoric acid ester out
Natrium-2,5-dichlor-4-methylsulfinylphenolat und 0,0-DimethylthionophosphorsäurechloridSodium 2,5-dichloro-4-methylsulfinylphenolate and 0,0-dimethylthionophosphoric acid chloride
Ausbeute 31 g (90% der Theorie) Molgewicht 349,21 Analyse:Yield 31 g (90% of theory) molecular weight 349.21 Analysis:
Berechnet ... P 8,87, S 18,36, Cl 20,26%; gefunden .... P 8,72, S 18,3, Cl 20,10%.Calculated ... P 8.87, S 18.36, Cl 20.26%; found .... P 8.72, S 18.3, Cl 20.10%.
c) O-Methyl-O-(2,5-dichlor-4-methylsulfinylphenyl)-methylthionophosphonsäureester ausc) O-methyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -methylthionophosphonic acid ester out
Natrium-2,5-dichlor-4-methylsulfinylphenolat undSodium 2,5-dichloro-4-methylsulfinylphenolate and
MethylthionophosphonsäuremethylesterchloridMethylthionophosphonic acid methyl ester chloride
Ausbeute 30 g (90% der Theorie; Molgewicht 333,21. Analyse:Yield 30 g (90% of theory; molecular weight 333.21. Analysis:
Berechnet ... P 9,30, S 19,28, Cl 21,28%; gefunden .... P 9,40, S 19,20, Cl 21,34%.Calculated ... P 9.30, S 19.28, Cl 21.28%; found .... P 9.40, S 19.20, Cl 21.34%.
d) O-Äthyl-O-(2,5-dichlor-4-methylsuIfinylphenyl)-methylthionophosphonsäureester ausd) O-ethyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -methylthionophosphonic acid ester out
Natnum-2,5-dichlor-4-melhyIsulfinylphenolat und MethylthionophosphonsäureäthylesterchloridNatnum-2,5-dichloro-4-melhyisulfinylphenolate and Methylthionophosphonic acid ethyl ester chloride
Ausbeute 30 gYield 30g
347,24.347.24.
Analyse:Analysis:
Berechnet
gefunden .Calculated
found .
e) O-Äthyl-O-(2,5-dichlor-4-methylsulfinylphenyl)-e) O-ethyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -
üthylthionophosphonsüurecster ausüthylthionophosphonsüurecster from
Natrium^^-dichloM-methylsulfinylphenolat und Äthylthionophosphonsäurcäthylesterchlorid Ausbeute 30 g (83% der Theorie), Molgewicht 361,26.Sodium ^^ - dichloM-methylsulfinylphenolate and Ethylthionophosphonic acid ethyl ester chloride Yield 30 g (83% of theory), molecular weight 361.26.
Analyse:Analysis:
Berechnet ... P 8,56, S 17,78, Cl 19,64%; ίο gefunden .... P 8,50, S 17,92, Cl 19,47%.Calculated ... P 8.56, S 17.78, Cl 19.64%; ίο found .... P 8.50, S 17.92, Cl 19.47%.
0 O-n-Propyl-O-(2,5-dichlor-4-methylsulfinyI-phenylj-methylthionophosphonsäureester aus Natrium-2,5-dichlor-4-methylsulfinylphenolat und Methylthionophosphorsäure-n-propylesterchloridO-n-Propyl-O- (2,5-dichloro-4-methylsulfinyI-phenylj-methylthionophosphonic acid ester from sodium 2,5-dichloro-4-methylsulfinylphenolate and methylthionophosphoric acid n-propyl ester chloride
Ausbeute 29 g (82% der Theorie), Molgewicht 361,26.Yield 29 g (82% of theory), molecular weight 361.26.
Analyse:
Berechnet
gefunden .Analysis:
Calculated
found .
(87% der Theorie); Molgewicht P 8,56, S 17,78, Cl 19,64%; P 8,47, S 17,86, Cl 19,80%».(87% of theory); Molecular weight P 8.56, S 17.78, Cl 19.64%; P 8.47, S 17.86, Cl 19.80% ».
g) O-Isopropyl-O-(2,5-dichlor-4-methylsulfinylphenyl)-methylthionophosphonsaureester aus Natriüm-2,5-dichlor-4-methylsulfinylphenolat und Methylthionophosphorsäureisopropylesterchloridg) O-Isopropyl-O- (2,5-dichloro-4-methylsulfinylphenyl) -methylthionophosphonic acid ester from sodium 2,5-dichloro-4-methylsulfinylphenolate and Isopropyl methylthionophosphoric acid ester chloride
Ausbeute 28 g (80% der Theorie), Molgewicht 361,26.Yield 28 g (80% of theory), molecular weight 361.26.
Analyse:Analysis:
Berechnet
gefunden .Calculated
found .
P 8,56, S 17,78, Cl 19,64%; P 8,50, S 17,52, Cl 19,52%.P 8.56, S 17.78, Cl 19.64%; P 8.50, S 17.52, Cl 19.52%.
h) O-ÄthyI-O-(2,5-dichlor-4-methylsuIfinylphenyl)-h) O-EthyI-O- (2,5-dichloro-4-methylsulfinylphenyl) -
phenylthionophosphonsäureester ausphenylthionophosphonic acid ester from
Natrium-2,5-dichlor-4-methylsulfinylphenolat und PhenylthionophosphonsäureäthylesterchloridSodium 2,5-dichloro-4-methylsulfinylphenolate and phenylthionophosphonic acid ethyl ester chloride
Ausbeute 33 g (82% der Theorie), Molgewicht 409,29.Yield 33 g (82% of theory), molecular weight 409.29.
Analyse:
Berechnet
gefunden .Analysis:
Calculated
found .
P 7,58, S 15,68, Cl 17,35%; P 7,42, S 15,60, C! 17,30%.P 7.58, S 15.68, Cl 17.35%; P 7.42, S 15.60, C! 17.30%.
Claims (3)
Family
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