BE659656A - - Google Patents
Info
- Publication number
- BE659656A BE659656A BE659656DA BE659656A BE 659656 A BE659656 A BE 659656A BE 659656D A BE659656D A BE 659656DA BE 659656 A BE659656 A BE 659656A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- agents
- formula
- carbon atoms
- thiol
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 159000000011 group IA salts Chemical class 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000003096 antiparasitic agent Substances 0.000 claims description 2
- 229940125687 antiparasitic agent Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- -1 aliphatic nitriles Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001414987 Strepsiptera Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- C07F9/28—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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
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)
Description
<EMI ID=1.1>
L'objet du brevet principal est un procédé de préparation
<EMI ID=2.1> et l'on fait réagir ensuite l'halogénure de �-cyanoéthylmercaptométhyle obtenu comme produit intermédiaire, sans purification ou isolation préalable, avec des acides dialcoylthiolou -thionothiolphosphoriques, -phosphoniques, -phosphiniques
<EMI ID=3.1>
<EMI ID=4.1>
de préférence sous forme des sels correspondants alcaline ou
<EMI ID=5.1>
<EMI ID=6.1>
alcoyle ou alcoxy identiques ou différents contenant de préfé- rence 1 à 4 atomes de carbone, tandis que X représente un atome d'oxygène ou de soufre.
D'après le procédé revendiqué dans le brevet principal on obtient des composés de structure générale
<EMI ID=7.1>
<EMI ID=8.1>
signification donnée plus haut.
Au cour? de travaux ultérieurs sur l'objet de l'invention, on vient de faire la découverte que la réaction d'halogénation
<EMI ID=9.1>
<EMI ID=10.1>
<EMI ID=11.1>
<EMI ID=12.1>
-aralooyl-) éthers de formule générale
<EMI ID=13.1>
Dans les formules qui précèdent R représente un groupe alcoyle ayant 2 à 6 atomes de oarbone, un reste aryle éventuellement halo-substitué, de préférence phényle, ou un reste araleoyle, de préférence benzyle, tandis que Hal est un atome d'halogène, surtout de chlore.
<EMI ID=14.1>
avantageusement sans purification ou isolation préalable - être mis à réagir avec des acides dialcoylthiol- ou -thionothiolphosphoriques, -phosphoniques, -phosphiniques de formule
<EMI ID=15.1>
<EMI ID=16.1>
de préférence sous forme des sels correspondants alcaline ou d'ammonium ou en présence d'agents fixateurs d'acide.
La réaction conforme à l'invention est illustrée par le
<EMI ID=17.1>
<EMI ID=18.1>
<EMI ID=19.1>
la même signification que plus haut.
Comme agents d'halogénation on envisage surtout le ohlorure de sulfuryle ou le chlore élémentaire. Le premier stade du procédé selon l'invention s'effectue déjà à de basses températures de manière aisée et avec une vitesse suffisante, et c'est pourquoi l'halogénation est de préférenoe exécutée entre
-20 et +10[deg.]C. L'utilisation de solvants ou diluants organiques inertes s'avère avantageuse. On envisage surtout les hydrocarbures aliphatiques chlorés comme le chlorure de méthylène, le tri- et le tétrachloréthylène, le chloroforme, le tétrachlorure de carbone ainsi que le. tri- et tétrachloréthane. En outre il <EMI ID=20.1>
<EMI ID=21.1>
<EMI ID=22.1> -phoephiniques cités préoédemment. Comme solvants ont donné en l'occurrence satisfaction surtout les oétones et nitriles aliphatiques inférieurs comme l'acétone, la méthyléthyl-, <EMI ID=23.1>
propionitrile. Il s'avère avantageux d'effectuer la réaction
<EMI ID=24.1>
et d'agiter encore le mélange de réaction ici aussi pendant un certain temps (30 minutes à 2 heures), éventuellement avec chauffage.
<EMI ID=25.1> .éthers nécessaires comme matières de départ pour le procédé selon l'invention sont obtenables facilement et avec de bons <EMI ID=26.1>
le tableau suivant on donne à titre d'exemple quelques représentants des composés à utiliser conformément à l'invention, en indiquant leurs propriétés physiques
<EMI ID=27.1>
<EMI ID=28.1> <EMI ID=29.1>
i
espèces les plus diverses d'insectes parasites, par exemple les mites fileuses, les pucerons, les chenilles et les mouches; c'est pourquoi ils trouvent une utilisation comme agents antiparasitaires ou respectivement comme agents de protection des plantes.
Les exemples suivants donnent un aperçu sur le procédé revendiqué.
<EMI ID=30.1>
<EMI ID=31.1>
<EMI ID=32.1>
<EMI ID=33.1>
on évapore alors le solvant à une température aussi basse que
<EMI ID=34.1>
<EMI ID=35.1>
ment de l'addition goutte à goutte on chauffe le mélange de
<EMI ID=36.1>
ensuite dans de l'eau glacée et on reprend l'huile déposée dans 300 cm3 de benzène. On lave la solution benzénique avec de l'eau et on la sèche ensuite sur du sulfate de sodium. Après
<EMI ID=37.1>
oyanoéthyle) sous forme d'huile de couleur jaune faible, insoluble dans l'eau.
<EMI ID=38.1>
<EMI ID=39.1>
<EMI ID=40.1>
mouches et les mites fileuses. ,
Exemple 2 :
<EMI ID=41.1>
<EMI ID=42.1>
éther dans 400 cm3 de chlorure de méthylène. A cette solution
<EMI ID=43.1>
on maintient encore le mélange de réaction pendant 30 minutes
<EMI ID=44.1>
<EMI ID=45.1>
<EMI ID=46.1>
<EMI ID=47.1>
<EMI ID=48.1>
Analyse : calculé pour un poids moléculaire de 255
<EMI ID=49.1>
Les solutions à 0,1% du produit tuent à 100% les mites fileuses*'
Exemple 3 :
<EMI ID=50.1>
On dissout 58 g (0,5 mole) de /3-cyanoéthyl-thioéthyl- éther dans 400 cm3 de chlorure de méthylène, on ajoute goutte à;
<EMI ID=51.1>
de sulfuryle, on agite le mélange ensuite encore 30 minutes à
<EMI ID=52.1>
<EMI ID=53.1>
tout en agitant à 30 - 40[deg.]C à 90 g de méthyl-0-méthyl-thiono- <EMI ID=54.1>
nitrile. Après achèvement de l'addition goutte à goutte on chauffe le mélange pendant encore une heure à 50-60*0 et l'on opère ensuite comme décrit à l'exemple 1. On obtient 88 g
<EMI ID=55.1>
incolore, Insoluble dans l'eau.
Analyse calculé pour un poids moléculaire de 255
<EMI ID=56.1>
<EMI ID=57.1>
fileuses.
<EMI ID=58.1>
<EMI ID=59.1>
On chlore une solution de 58 g (0,5 mole) de /3-oyanoéthyl-thioéthyléther dans 400 cm3 de chlorure de méthylène à
<EMI ID=60.1>
le solvant à basse température. On ajoute goutte à goutte
<EMI ID=61.1>
<EMI ID=62.1>
<EMI ID=63.1>
<EMI ID=64.1>
<EMI ID=65.1>
<EMI ID=66.1>
<EMI ID=67.1>
<EMI ID=68.1>
Exemple 5.
<EMI ID=69.1>
<EMI ID=70.1>
<EMI ID=71.1>
rure de eulfuryle, on agite enduite le mélange pendant encore
<EMI ID=72.1>
<EMI ID=73.1>
thio-(4-onlorophényl)éther ainsi obtenu tout en agitant à
20-30[deg.]C à 112 g d'0,0-diéthyl-thionothiolphosphate de potassium dissous dans 300 cm3 d'acétonitrile. Ensuite on chauffe le mélange encore une heure à 60[deg.]C, puis on opère de la manière
<EMI ID=74.1>
cyanoéthyle/ sous forme d'huile jaune insoluble dans l'eau.
<EMI ID=75.1>
<EMI ID=76.1>
Les solutions à 0,001� du composé tuent encore à concurrence de 65� les mites fileuses.
De la même manière on obtient par réaction du (3 -cyano-
<EMI ID=77.1>
<EMI ID = 1.1>
The subject of the main patent is a preparation process
<EMI ID = 2.1> and the � -cyanoethylmercaptomethyl halide obtained as an intermediate product is then reacted, without prior purification or isolation, with dialkylthiolou -thionothiolphosphoric, -phosphonic, -phosphinic acids
<EMI ID = 3.1>
<EMI ID = 4.1>
preferably in the form of the corresponding alkaline salts or
<EMI ID = 5.1>
<EMI ID = 6.1>
The same or different alkyl or alkoxy preferably containing 1 to 4 carbon atoms, while X represents an oxygen or sulfur atom.
According to the process claimed in the main patent, compounds of general structure are obtained
<EMI ID = 7.1>
<EMI ID = 8.1>
meaning given above.
The heart? of subsequent work on the subject of the invention, we have just made the discovery that the halogenation reaction
<EMI ID = 9.1>
<EMI ID = 10.1>
<EMI ID = 11.1>
<EMI ID = 12.1>
-aralooyl-) ethers of general formula
<EMI ID = 13.1>
In the above formulas, R represents an alkyl group having 2 to 6 carbon atoms, an optionally halo-substituted aryl residue, preferably phenyl, or an araleoyl residue, preferably benzyl, while Hal is a halogen atom, especially of chlorine.
<EMI ID = 14.1>
advantageously without prior purification or isolation - be reacted with dialkylthiol- or -thionothiolphosphoric, -phosphonic, -phosphinic acids of formula
<EMI ID = 15.1>
<EMI ID = 16.1>
preferably in the form of the corresponding alkaline or ammonium salts or in the presence of acid scavenging agents.
The reaction in accordance with the invention is illustrated by
<EMI ID = 17.1>
<EMI ID = 18.1>
<EMI ID = 19.1>
the same meaning as above.
Particularly suitable halogenating agents are sulfuryl chloride or elemental chlorine. The first stage of the process according to the invention is already carried out at low temperatures easily and with a sufficient speed, and that is why the halogenation is preferably carried out between
-20 and +10 [deg.] C. The use of inert organic solvents or diluents proves to be advantageous. Chlorinated aliphatic hydrocarbons such as methylene chloride, tri- and tetrachlorethylene, chloroform, carbon tetrachloride as well as. tri- and tetrachloroethane. Additionally there <EMI ID = 20.1>
<EMI ID = 21.1>
<EMI ID = 22.1> -phoephinics mentioned above. As solvents in this case have given satisfaction above all oetones and lower aliphatic nitriles such as acetone, methylethyl-, <EMI ID = 23.1>
propionitrile. It is advantageous to carry out the reaction
<EMI ID = 24.1>
and further stir the reaction mixture here too for a while (30 minutes to 2 hours), optionally with heating.
<EMI ID = 25.1>. Ethers required as starting materials for the process according to the invention are obtainable easily and with good <EMI ID = 26.1>
the following table gives by way of example some representatives of the compounds to be used in accordance with the invention, indicating their physical properties
<EMI ID = 27.1>
<EMI ID = 28.1> <EMI ID = 29.1>
i
the most diverse species of parasitic insects, for example spinning mites, aphids, caterpillars and flies; therefore they find use as antiparasitic agents or respectively as plant protection agents.
The following examples give an overview of the claimed process.
<EMI ID = 30.1>
<EMI ID = 31.1>
<EMI ID = 32.1>
<EMI ID = 33.1>
the solvent is then evaporated off at a temperature as low as
<EMI ID = 34.1>
<EMI ID = 35.1>
of the dropwise addition, the mixture is heated
<EMI ID = 36.1>
then in ice water and the oil deposited in 300 cm3 of benzene. The benzene solution is washed with water and then dried over sodium sulfate. After
<EMI ID = 37.1>
oyanoethyl) as a faint yellow oil, insoluble in water.
<EMI ID = 38.1>
<EMI ID = 39.1>
<EMI ID = 40.1>
flies and spinning moths. ,
Example 2:
<EMI ID = 41.1>
<EMI ID = 42.1>
ether in 400 cm3 of methylene chloride. To this solution
<EMI ID = 43.1>
the reaction mixture is still maintained for 30 minutes
<EMI ID = 44.1>
<EMI ID = 45.1>
<EMI ID = 46.1>
<EMI ID = 47.1>
<EMI ID = 48.1>
Analysis: calculated for a molecular weight of 255
<EMI ID = 49.1>
0.1% solutions of the product kill 100% spinning moths * '
Example 3:
<EMI ID = 50.1>
58 g (0.5 mol) of / 3-cyanoethyl-thioethyl-ether are dissolved in 400 cm3 of methylene chloride, and are added dropwise to;
<EMI ID = 51.1>
sulfuryl, the mixture is then stirred for a further 30 minutes at
<EMI ID = 52.1>
<EMI ID = 53.1>
while stirring at 30 - 40 [deg.] C to 90 g of methyl-0-methyl-thiono- <EMI ID = 54.1>
nitrile. After completion of the dropwise addition, the mixture is heated for a further hour at 50-60 ° 0 and the procedure is then carried out as described in Example 1. 88 g are obtained.
<EMI ID = 55.1>
colorless, Insoluble in water.
Analysis calculated for a molecular weight of 255
<EMI ID = 56.1>
<EMI ID = 57.1>
spinners.
<EMI ID = 58.1>
<EMI ID = 59.1>
A solution of 58 g (0.5 mol) of / 3-oyanoethyl-thioethyl ether in 400 cm3 of methylene chloride is chlorinated at
<EMI ID = 60.1>
the solvent at low temperature. We add drop by drop
<EMI ID = 61.1>
<EMI ID = 62.1>
<EMI ID = 63.1>
<EMI ID = 64.1>
<EMI ID = 65.1>
<EMI ID = 66.1>
<EMI ID = 67.1>
<EMI ID = 68.1>
Example 5.
<EMI ID = 69.1>
<EMI ID = 70.1>
<EMI ID = 71.1>
eulfuryl rure, the mixture is stirred for a further
<EMI ID = 72.1>
<EMI ID = 73.1>
thio- (4-onlorophenyl) ether thus obtained while stirring at
20-30 [deg.] C at 112 g of potassium 0,0-diethyl-thionothiolphosphate dissolved in 300 cm3 of acetonitrile. Then the mixture is heated for another hour at 60 [deg.] C, then the procedure is carried out as
<EMI ID = 74.1>
cyanoethyl / as yellow oil insoluble in water.
<EMI ID = 75.1>
<EMI ID = 76.1>
The solutions at 0.001 � of the compound still kill up to 65%. spinning moths.
In the same way one obtains by reaction of (3 -cyano-
<EMI ID = 77.1>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41994A DE1200806B (en) | 1964-02-13 | 1964-02-13 | Process for the production of thiol or thionothiolphosphorus (-phosphonic, -phosphine) - acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE659656A true BE659656A (en) | 1965-05-28 |
Family
ID=7098898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE659656D BE659656A (en) | 1964-02-13 | 1965-02-12 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE659656A (en) |
| DE (1) | DE1200806B (en) |
-
1964
- 1964-02-13 DE DEF41994A patent/DE1200806B/en active Pending
-
1965
- 1965-02-12 BE BE659656D patent/BE659656A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1200806B (en) | 1965-09-16 |
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