CH494247A - Process for the preparation of phosphoric or phosphonic or thionophosphorus or thionophosphonic acid esters - Google Patents

Description

  

  
 



  Process for the production of phosphorus or phosphonic or thionophosphorus or
Thionophosphonic acid esters
The present invention enters into a process for the production of new phosphorus or phosphonic or



  Thionophosphorus or thionophosphonic acid esters of the general formula
EMI1.1
 which have insecticidal and acaricidal properties.



   In the above formula, Rt stands for a straight or branched alkoxy radical with 1 to 6 carbon atoms, optionally substituted one or more times by halogen atoms, or a lower alkylamino or dialkylamino group, R2 stands for a lower alkyl, alkylamino, dialkylamino, alkoxy or the phenyl radical, while X represents an oxygen or sulfur atom.



   US Pat. No. 3,284,455 already discloses phosphonic and thionophosphonic acid quinolyl esters. These products are obtained by reacting alkyl or aryl (thiono) phosphonic acid O-alkyl ester halides with the corresponding hydroxychnolines.



   According to the information in the patent cited above, the compounds in question are characterized by good insecticidal and acaricidal properties and are therefore suitable for controlling aphids, spider mites, flies, ticks, etc.



   It has now been found that compounds of the general structure (I) are obtained if phosphorus or phosphonic or thionophosphorus or thionophosphonic acid ester halides of the general formula
EMI1.2
 with 2-hydroxy-4-methyl-quinoline (2-hydroxy-lepidine).



   In the latter formula, R1, R2 and X have the meaning given above, while Hal stands for a halogen atom.



   The products of the process of constitution (I) are distinguished by their excellent insecticidal properties. They have an excellent effect against both eating and sucking insects and are very effective against spider mites and ticks. In this regard, the compounds that can be prepared according to the invention are clearly superior to the above-mentioned known products of analogous constitution, the former thus represent a real enrichment of technology.



   The course of the process according to the invention is explained in more detail using the following reaction scheme:
EMI2.1

In the last-mentioned equation, the symbols R1, R2, X and Hal have the meaning given above. BeL preferably, however, Rt denotes a lower alkoxy, alkylamino or dialkylamino radical, each with 1 to 4 carbon atoms, such as methoxy, ethoxy.



  2-chloroethoxy, 2,2,2-trichloroethoxy, n- and isopropoxy, is and sec., Butoxy, N-methyl, N-ethyl, N-propyl, N-isopropyl, N- Butyl-, N-isobutyl-, N-sec-butyl- and N-tert-butylamino-, N, N-dimethyl-, N, N-diethyl-, N, N-dipropyl-, N, N-di -isopropyl, N, N-dibutyl and N, N-diisobutylamino radicals; R2 preferably has one of the meanings given above for Rt, where R1 and R2 can be identical to or different from one another; furthermore, R2 preferably represents an alkyl group having 1 to 4 carbon atoms, e.g.

  B. the methyl, ethyl, 2-chloroethyl, n- and isopropyl, n-, iso- and sec-butyl and the phenyl radical; X primarily represents a sulfur and Hal a chlorine or bromine atom.



   The 2-hydroxy-4-methylquinoline (2-hydroxy-lepidine) required as the starting material for the implementation according to the process is already known from the literature and can be prepared, for example, from acetoacetic anilide by the method described in Liebigs Annalen der Chemie, Vol. 236, page 83 a ring closure reaction can be produced using sulfuric acid.



   In the reaction according to the process, the 2-hydroxy-4-methyl-quinoline is preferably used in the form of its salts. The corresponding alkali (especially sodium and potassium), alkaline earth and ammonium salts, but also heavy metal salts, e.g. B. of silver.



   Instead of working with the relevant salts, however, it is also possible to allow the reaction to proceed in the presence of acid binders. Practically all common acid acceptors can be used for this purpose. However, alkali alcoholates and carbonates, such as sodium and potassium methylate or ethylate and potassium and sodium carbonate, and also tertiary aliphatic, aromatic or heterocyclic amines, for example triethylamine, dimethylaniline, dimethylbenzylamine or pyridine, have proven particularly suitable.



   The process according to the invention is preferably carried out with the use of suitable solvents and diluents. Practically all inert organic solvents or mixtures thereof come into consideration as such, such as hydrocarbons, e.g.



  Gasoline, benzene, toluene, chlorobenzene, xylene, ethers, for example diethyl and dibutyl ethers, dioxane, and also ketones, e.g. B.



  Acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone; However, low-boiling aliphatic alcohols, for example methanol, ethanol and, above all, nitriles, e.g. B. aceto- and propionitrile, also dimethylformamide.



   When carrying out the reaction according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the temperature is between 10 and 800 ° C. (or the boiling point of the mixture), preferably at 20 to 600 ° C.



  The starting materials to be reacted in accordance with the process and any auxiliaries (acid binders) to be used are generally used in equimolar amounts.



   After combining the starting components, it is advantageous to post-heat the mixture for a longer time (about 1 to 3 hours), if necessary with stirring, in order to complete the reaction. In this procedure, the process products are obtained in excellent yields and in excellent purity.

 

   The phosphorus, or phosphonic or thionophosphorus or thiophosphonic acid esters which can be prepared according to the present invention are usually obtained in the form of colorless to yellow-colored, viscous, water-insoluble, non-decomposable oils that cannot be distilled without being distilled, however. H. Prolonged heating under reduced pressure to moderately elevated temperatures freed from the last volatile components and cleaned in this way. The determination of the refractive index can be used to characterize it more closely
As already mentioned above, the products of the process are distinguished by their excellent insecticidal and acaricidal effectiveness. At the same time, they only have a low level of warm-blooded animals and phytotoxicity. It takes effect quickly and lasts for a long time.

  For this reason, the compounds which can be prepared according to the invention can be used successfully in crop protection for combating harmful sucking and eating insects and diptera and there and in the veterinary medical sector against mites (acarina). Particularly noteworthy in this context is the excellent effectiveness of the products against phosphoric acid ester-resistant strains of spider mites.



   The sucking insects essentially include aphids (Aphidae) such as the green peach aphid (Myzus persicae), the black bean (Doralis fabae), oat (Rhopalosiphum padi.), Peas (Macrosiphum pisi) and potato mouse (Macrosiphum solanifolii) the currant gall (Cryptomyzus korschelti), floury apple (Sappaphis mali), floury plum (Hyalopterus arundinis) and black cherry aphid (Myzus cerasi), as well as shield and mealybugs (Coccina), e.g.

  B. the ivy shield (Aspidiotus hederae) and cup louse (Lecanium hesperidum) and the mealybug (Pseudococcus maritimus); Bladder feet (Thysanoptera) such as Hercinothrips femoralis and bed bugs, for example, beets (Piesma quadrata), cotton (Dysdercus intermedius), bed (Cimex lectularius), predatory bug (Rhodnius prolixus) and Chagas bug (Triatoma infestans), and also cicadas such as Euscelis bilobatus and Nephotettix bipunctatus.



   Among the biting insects, the following should be mentioned above all: Butterfly caterpillars (Lepidoptera) such as the cabbage moth (Plutella maculipennis), the gypsy moth (Lymantria dispar), golden oyster (Euproctis chrysorrhoea) and ring moth (Malacosoma neustria), furthermore the cabbage (Mamestra brassicae) and the seed owl (Agrotis segetum), the large cabbage whitefly (Pie ris brassicae), small frostworm (Cheimatobia bromata), oak moth (Tortrix viridana), the army (Laphygma frugiperda) and Egyptian cottonworm (Prodenia litura), also the web ( Hyponomeuta padella) flour (Ephestia Kühniella) and large wax moth (Galleria mellonella). The biting insects also include beetles (Coleoptera) e.g.



  Corn (Sitophilus granarius = Calandra granaria), potato (Leptinotarsa decemlineata), dock (Gastrophysa viridula), horseradish leaf (Phaedon cochleariae), rapeseed (Meligethes aeneus), raspberry (Byturus tomentosus =), edible beans Acanthoscelides obtectus), bacon (Dermestes fresh), khapra (Trogoderma granarium), red-brown rice flour (Tribolium castaneum), corn (Calandra or Sitophilus zeamais), bread (Stegobium paniceum), common meal beetle (Tenebrio molitor) and beetles (Oxyzaephilus surinamensis), but also species living in the ground, e.g. B.

  Wireworms (Agriotes spec.) And white grubs (Melolontha melolontha); Cockroaches such as the German (Blatella germanica), American (Periplaneta americana), Madeira (Laucophaea or Rhyparobia madeirae), oriental (Blatta orientalis), giant (Blaberus giganteus) and giant black cockroach (Blaberus fuscus) as well as Henschoutedenia flexivitta; also orthopter z. B. the cricket Gryllus domesticus); Termites such as the terrestrial termites (Reticulitermes flavipes) and Hymenoptera such as ants, for example the meadow ant (Lasius niger).



   The dipteras essentially include flies such as the dew (Drosophila melanogaster), Mediterranean fruit (Ceratitis capitata), house (Muscadomestica), small house (Fannia canicularis), glossy fly (Phormia aegina) and blow fly (Calliphora erythrocephala) and the calf trigger (Stomoxys calcitrans); also Mükken, z. B. Mosquitoes like the yellow fever (Aedes aegypti), house mosquito (Culex pipiens) and malaria mosquito (Anopheles stephensi).



   The mites (Acari) include the spider mites (Tetranychidae) such as the bean (Tetranychus telarius = Tetranychus althaeae or Tetranychus urticae) and the fruit tree spider mite (Paratetranychus pilosus = Panonychus ulmi), gall mites e.g. B. the currant mite (Eriophyes ribis) and tarsonemids, for example the shoot tip mite (Hemitarsonemus latus) and cyclamen mite (Tarsonemus pallidus); and finally ticks like the leather tick (Ornithodorus moubata).



   When used against hygiene pests and pests of stored products, especially flies and mosquitoes, the products of the process are also distinguished by an excellent residual effect on wood and clay and good alkali stability on limed substrates.



   Depending on their intended use, the new active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are made in a known manner, e.g. B. by mixing the active ingredients with extenders, d. H. liquid solvents and / or solid carriers, optionally using surface-active agents that is emulsifying and / or dispersing agents, where z. B. in the case of the use of water as an extender, organic solvents can optionally be used as auxiliary solvents. The following liquid solvents are essentially: aromatics (e.g. xylene, benzene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g.

  Methanol, butanol), strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water; as solid carrier materials: natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g.



  highly disperse silica, silicates); as emulsifiers: nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alylaryl polyglycol ether, Alylsulfonate and Arylsulfonate) as a dispersant z. B. lignin, sulphite waste liquors and methyl cellulose.



   The active ingredients according to the invention can be present in the formulations as a mixture with other known active ingredients. The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90% by weight.

 

   The active ingredient concentrations can be varied within a larger range. In general, concentrations of from 0.00001% to 20%, preferably from 0.01% to 5%, are used.



   The active compounds 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. It is used in the usual way, e.g. by pouring, spraying, atomizing, gasifying, smoking, scattering, dusting, etc.



   Surprisingly, the process products are distinguished, compared to the active ingredients of an analogous constitution and the same direction of action known from the literature, by a significantly better effectiveness with a considerably lower toxicity to the wanmother. They therefore represent a real enrichment of technology. This unexpected superiority and the excellent effect of the compounds which can be prepared according to the method when used against a large number of pests and animal parasites can be seen from the following test results:
Example A LDt00 test
Test animals: grain beetle (Sitophilus granarius) Solvent: acetone
2 parts by weight of active ingredient are taken up in 1000 parts by volume of solvent.

  The solution thus obtained is diluted to the desired concentrations with further solvent.



   2.5 ml of the active ingredient solution are pipetted into a Petri dish. On the bottom of the Petri dish there is a filter paper with a diameter of about 9.5 cm. The Petri dish remains open until the solvent has completely evaporated. Depending on the concentration of the active ingredient solution, the amount of active ingredient per m2 of filter paper varies. Then about 25 test animals are placed in the Petri dish and covered with a glass lid.



   The condition of the test animals is checked after 1 and 3 days after the experiments have been started. The knock down effect is determined in O / o.



     Active ingredients, active ingredient concentrations, test animals and results are shown in Table 1 below:
Table I LDtoo test
EMI4.1


<tb> Active ingredient <SEP> (constitution) <SEP> Active ingredient concentration <SEP> knock-down effect
<tb> <SEP> jn0 / O <SEP> in <SEP> O / o
<tb> <SEP> CH8
<tb> <SEP> 42 <SEP> 100
<tb> <SEP> 5 <SEP> 0.02 <SEP> 100
<tb> <SEP> No-P- (oC2H5) 2 <SEP> 0; 002 <SEP> 0
<tb> <SEP> CH3
<tb> 03 <SEP> 0-S <SEP> / CHs <SEP> 42 <SEP> 100
<tb> <SEP> OPs <SEP> 0.02 <SEP> 100
<tb> <SEP> 0.02 <SEP> 100
<tb> <SEP> OC2H5 <SEP> 0.002 <SEP> 60
<tb> <SEP> C1
<tb> <SEP> N / SI / CH3 <SEP> 0.2 <SEP> 100
<tb> <SEP> O - P
<tb> <SEP> OC2Hs
<tb> (known <SEP> comparator preparation)
<tb> 0 <SEP> 5 <SEP> CH3 <SEP> 0.2 <SEP> 60
<tb> N <SEP> -h.
<tb>



   <SEP> o-P
<tb> <SEP> OC2H5
<tb> (known <SEP> comparator preparation)
<tb>
Example B LTt00 test for Diptera
Test animals: mosquito larvae (Aedes aegypti)
Solvent: acetone
2 parts by weight of active ingredient are taken up in 1000 parts by volume of solvent. The solution obtained in this way is diluted to the desired lower concentrations with further solvent.



   2.5 ml of the active ingredient solution are pipetted into a Petri dish. On the bottom of the Petri dish there is a filter paper with a diameter of about 9.5 cm. The Petri dish remains open until the solvent has completely evaporated. Depending on the concentration of the active ingredient solution, the amount of active ingredient per m2 of filter paper varies. Then about 25 test animals are placed in the Petri dish and covered with a glass lid.



   The condition of the test animals is updated every hour up to 3
Hours controlled. The time is determined which is necessary for a 100 0 / above knock-down effect. (LTtoo)
Test animals, active ingredients, active ingredient concentrations and times at which there is a 100% knock-down effect are shown in Table 2 below:

  :
Table 2 LTtOO test for diptera
EMI5.1

 Active ingredient <SEP> (constitution) <SEP> Active ingredient concentration <SEP> LTtoo <SEP> in <SEP> minutes
<tb> <SEP> of the <SEP> solution <SEP> in <SEP> Oio
<tb> <SEP> CH8
<tb> <SEP> 0.2 <SEP> 60
<tb> <SEP> S <SEP> 0.02 <SEP> 60
<tb> <SEP> \ / <SEP> N <SEP> OPHOC2H5) 2 <SEP> 0.002 <SEP> 180
<tb> <SEP> CH8
<tb> <SEP> IS <SEP> CHs <SEP> 0.2 <SEP> 60
<tb> <SEP> N <SEP> O-P <SEP> 0.02 <SEP> 120
<tb> <SEP> OC2H5 <SEP> 0.002 <SEP> 180
<tb> <SEP> C1
<tb> <SEP> 0 <SEP> CHJ <SEP> 0.2 <SEP>> <SEP> 180
<tb> <SEP> N
<tb> <SEP> oc ± Hs
<tb> <SEP> (known <SEP> comparator preparation)
<tb> <SEP> 2 <SEP> 9 <SEP> gSxCHs <SEP> 0.2 <SEP> 180
<tb> <SEP> O - P
<tb> <SEP> OC2H5
<tb> <SEP> (known <SEP> comparator preparation)
<tb> Table 2 (continued) LTt0O test for dipteras
EMI6.1


<tb> active ingredient

   <SEP> (constitution) <SEP> Active ingredient concentration <SEP> LTtoo <SEP> in <SEP> minutes
<tb> <SEP> the <SEP> solution <SEP> in <SEP> / o
<tb> <SEP> 5 <SEP> CH3 <SEP> 0.2 <SEP> to <SEP> 60
<tb> <SEP> N <SEP> O-P <SEP> 0.02 <SEP>> <SEP> 180
<tb> <SEP> OC2H5
<tb> (known <SEP> comparator preparation)
<tb> <SEP> S <SEP> CHs
<tb> <SEP> 1 /
<tb> <SEP> o-P
<tb> OcHs <SEP> CHs <SEP> 0.2 <SEP>> <SEP> 180
<tb> (known <SEP> comparative preparation, council)
<tb>
Example C
Mosquito larva test
Test animals Aedes aegypti (5th larval stage) Solvent: 99 parts by weight acetone Emulsifier: 1 part by weight O-benzyl-oxydiphenylp olyglycol ether
To produce an appropriate preparation of active ingredient, 2 parts by weight of active ingredient are dissolved in 1000 parts by volume of solvent which contains the emulsifier in the amount indicated above.

  The solution thus obtained is diluted with water to the desired lower concentrations.

 

   The aqueous active ingredient preparations are filled into glasses and about 25 mosquito larvae are then placed in each glass.



   After 24 hours, the degree of destruction is determined in o / o. 100% means that all larvae have been killed. 0 O / o means that no larvae have been killed at all.



   Active ingredients, active ingredient concentrations, test animals and results are shown in Table 3 below:
Table 3 Mosquito larvae test
EMI6.2


<tb> Active ingredient <SEP> (constitution) <SEP> Active ingredient concentration <SEP> Degree of destruction <SEP> in <SEP> O / o
<tb> <SEP> the <SEP> solution <SEP> in <SEP> o / o
<tb> 0.001 <SEP> 100
<tb> <SEP> II <SEP> 00001 <SEP> 100
<tb> <SEP> 0.0001 <SEP> o, ocl <SEP> 0.00 &commat; 1 <SEP> 20
<tb> <SEP> - (OC2HO) 2 <SEP> 0.00001 <SEP> 20
<tb> Table 3 (continued)
Mosquito larva test
EMI7.1


<tb> Active ingredient <SEP> (constitution) <SEP> Active ingredient concentration <SEP> Degree of destruction <SEP> in <SEP> O / o
<tb> <SEP> of the <SEP> solution <SEP> in <SEP> O / o
<tb> <SEP> CHs
<tb> <SEP> S <SEP> CHs <SEP> o, ool <SEP> loo
<tb> <SEP> II /
<tb> N <SEP> oP \ <SEP> o0;

  ; ooo001i <SEP> 100
<tb> <SEP> OC2Hs <SEP> 0.00001 <SEP> o
<tb> <SEP> Cl
<tb> yiS17CH3 <SEP> O, 00t <SEP> 0
<tb> <SEP> P
<tb> <SEP> OC2Hs
<tb> (known <SEP> comparator preparation)
<tb> NX <SEP> ISl <SEP> / CHs <SEP> 0.001 <SEP> So
<tb> <SEP> 11 /
<tb> <SEP> P <SEP> Ps <SEP> 0.001 <SEP> o
<tb> <SEP> OC2H6
<tb> <SEP> (known <SEP> comparator preparation)
<tb> <SEP> 8 <SEP> CH3
<tb> <SEP> 8 /
<tb> <SEP> o-p
<tb> <SEP> / OC2Hs <SEP> 0.001 <SEP> 80
<tb> <4 <SEP> 0.0001 <SEP> 0
<tb> <SEP> (known <SEP> comparator preparation)
<tb>
Example D
Drosophila test Solvent: 3 parts by weight acetone Emulsifier:

   1 part by weight of acylaryl polyglycol ether
To produce a suitable preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount of solvent which contains the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.



   1 cm3 of the active ingredient preparation is pipetted onto a filter paper disk with a diameter of 7 cm.



  They are placed wet on a glass in which there are 50 fruit flies (Drosophila melanogaster) and covered with a glass plate.



   After the specified times, the destruction in O / o is determined. 100% means that all flies have been killed, 0% means that no flies have been killed.



   Active ingredients, active ingredient concentrations, evaluation times and degree of destruction are shown in Table 4 below: Table 4
EMI8.1


<tb> Active ingredient <SEP> (constitution) <SEP> Active ingredient corcentage <SEP> in <SEP> O / o <SEP> Degree of destruction <SEP> in <SEP> O / o
<tb> <SEP> after <SEP> 24 <SEP> hours
<tb> C-wH50 <SEP> S
<tb> <SEP> P-o <SEP> 0.1 <SEP> 100
<tb> <SEP> CH¯ <SEP> AN <SEP> 0.01 <SEP> 0
<tb> (known <SEP> comparator preparation)
<tb> <SEP> CH3
<tb> <SEP> 0.1 <SEP> 100
<tb> (C2H50) 2P¯oA <SEP> 0.01 <SEP> lOo
<tb> <SEP> N <SEP> \ / <SEP> 0.001 <SEP> 99
<tb> <SEP> CH3
<tb> C2H50 <SEP> 5
<tb> <SEP> 0.1 <SEP> 100
<tb> <SEP> CH¯ <SEP> N <SEP> o, ol <SEP> 95
<tb>
Example E
Myzus test (contact effect) Solvent: 3 parts by weight acetone Emulsifier:

   1 part by weight of alkylaryl poly glycol ether
To produce a suitable preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount of solvent which contains the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.



   Cabbage plants (Brassica oleracea) which are heavily infested with peach leaf lice (Myzus persicae) are sprayed to runoff with the preparation of the active compound.



   After the specified times, the degree of destruction is determined in 0/0. 100% means that all aphids have been killed, 0% means that none of the aphids have been killed.



   Active ingredients, active ingredient concentrations, evaluation times and results are shown in Table 5 below: Table 5
EMI9.1


<tb> Active ingredient <SEP> (constitution) <SEP> Active ingredient concentration <SEP> in <SEP> Olo <SEP> Killing <SEP> in <SEP> / o
<tb> <SEP> after <SEP> 24 <SEP> hours
<tb> <SEP> CH8
<tb> <SEP> 5
<tb> P-o <SEP> P-O <SEP> 0.1 <SEP> 100
<tb> (CeH50) 2 '<SEP> 0.01 <SEP> 80
<tb> <SEP> CH8
<tb> C2HsO \ <SEP> 5 <SEP> 0.1 <SEP> 100
<tb> <SEP> -o <SEP> 0.01 <SEP> 100
<tb> <SEP> CHW <SEP> N <SEP> \ / <SEP> 0.001 <SEP> 60
<tb>
The following examples illustrate the claimed process:
Example I.
EMI9.2
 36 g (0.2 mol) of the sodium salt of 2-hydroxy4-methyl-quinoline are suspended in 100 cc of acetonitrile.

  39 g (0.2 mol) of 0,0-diethyl-thionophosphoric acid ester chloride are added to this suspension at 600.degree. C., the reaction mixture is heated to 700.degree. C. for 5 hours and then stirred for several hours at room temperature. The sodium chloride which has precipitated out is then extracted by shaking and the 0 [4-methyl-quinolyl- (2) j ester remaining after the solvent has been distilled off is distilled off under greatly reduced pressure. The yield is 26 g (42% of theory).



   Analysis for C14H18NO8PS (molecular weight 311):
Calculated: N 4.51%; P 9.99 0 / o; S 10.3%
Found: N 4.510 / 0; P 10.25 / o; S 10.67 0/0
In an analogous manner, the compound of the formula
EMI9.3
 with a yield of 27 ovo of theory.

 

   Analysis for Ct3HlNO2PS (molecular weight 281):
Calculated: N 4.99%;
Found N 4.77%.



   Furthermore, the combination of the following constitution is also accessible according to the procedure given above:
EMI9.4

The yield is 300/0 of theory, the melting point is 72 to 740 C.



   Analysis for C18H18NO2PS (molecular weight 343):
Calculated: N 4.09 0 / o; P 9.05 0 / o; S 9.34 / o;
Found: N 3.68%; P 9.16%; S 9.950 / 0.

 

Claims (1)

PATENT CLAIM I Process for the preparation of phosphoric or phosphonic or thionophosphorus or thionophosphonic acid esters of the formula EMI10.1 characterized in that one phosphorus or phosphonic or thionophosphorus or thionophosphonic acid ester halides of the general formula EMI10.2 with 2-hydroxy-4-methylquinoline, where in the aforementioned formula R represents a straight or branched alkoxy radical with 1 to 6 carbon atoms, optionally substituted one or more times by halogen atoms, or a lower alkylamino or dialkylamino group, R2 represents a lower alkyl , Alkylamino, dialkylamino, or sulfur atom and Hal represents a halogen atom. PATENT CLAIM II Use of the compounds obtained by the process according to claim I as at least one active component in insecticidal and acaricidal agents.