IL43034A - Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them - Google Patents

Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them

Info

Publication number
IL43034A
IL43034A IL43034A IL4303473A IL43034A IL 43034 A IL43034 A IL 43034A IL 43034 A IL43034 A IL 43034A IL 4303473 A IL4303473 A IL 4303473A IL 43034 A IL43034 A IL 43034A
Authority
IL
Israel
Prior art keywords
carbon atoms
formula
radical
compound
kyl
Prior art date
Application number
IL43034A
Other versions
IL43034A0 (en
Original Assignee
Roussel Uclaf
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf filed Critical Roussel Uclaf
Publication of IL43034A0 publication Critical patent/IL43034A0/en
Publication of IL43034A publication Critical patent/IL43034A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

43034/2 ) PHOSPHORUS-CONTAINING ESTERS OF CONDENSED RING P'IRIMIDINE DERIVATIVES, PROCESS FOR THE PREPARATION OF THESE AND COMPOSITIONS CONTAINING THEM ΓΠ1Π3 ΙΪΒ2Β 017 Τ»-ΡΠ"«Τ>3 «11 111 70 0*nODR m7-»:ran imnirm omarr? "v nn »imt o^aon Π7Κ J1R in which Hal represents a chlorine or bromine atom and R^ and R^ have the. meaning already indicated, in the presence of a hydracid' acceptor.
In a preferred method of working a chlorophosphate is . used as halogeno phosphate of formula III.
The condensation reaction is carried out in an organic solvent such as acetone, ethyl acetate or acetonitrile, in the presence of a hydracid . acceptor such as potassium . , carbonate, triethylamine or pyridine.
The products of formula II, used at the start of the. ■ process of the invention, ma be prepared by condensing a 2-amino-pyridine or a 2-aminopyrimidine , both possibly \ substituted, with a possibly substituted. alky1 or aryl malonate.
The products of formula II, in which R^ represents a chlorine or bromine atom, may be obtained by the action of N-chloro or. N-bromo succinimide on the products of formula II, in which R^ represents hydrogen.
"Finally the products of formula II, in which R, represents: an alkyloxycarbonyl radical,y»iay be prepared by the action of a trisalkyloxycarbonylmethane on an arainopyridine or an aminopyrimidine , both possibly substituted.
The invention also includes pesticidal, in particular insecticidal, nematocidal or acaricidal compositions containin as active material one, at least, of the compounds of formula I. These compositions may appear in the form of powders, granules, suspensions, emulsions and solutions, containing the active · principle, for example in admixture with a vehicle and/or an anionic, cationic or non-ionic surface-active agent, ensuring, inter alia, uniform dispersion of the substances of the Composition. The vehicle used maybe a liquid such as water, alcohol, hydrocarbons or other organic solvents, a mineral, ; :: silicates or kieselguhr. . .
The insecticidal, nematocidal or acaricidal liquids or powders preferably contain from 5 to 9596 by weight of active j ·'■ : material. ί ' ' '."\·-·-. ' ' As insecticidal composition there, is used, for example, j . an emulsifiable concentrate containing, by weight., 15% of i ; 2-(dimethoxythiophosphoryloxy) pyrido 2,laJ pyrimidine 4-one, 6.4 % of Atlox 4851 (o.xyethylenated triglyceride combined with a I sulphonate, acid inde : 1.5)» 5.2 % of Atlox 4855 (oxyethylenated | j triglyceride combined with a sulphonate, acid index : 3) and 75.4 % of xylene. · · In insecticidal, nematocidal or acaricidal control, a composition containing as active material one, at least, of the compounds of formula I, possibly mixed with one or more other pesticidal agents, may be used. : . ' '·'. - ■ ■ ■· ■ .· . '·' - ■:'·,· ■ '.. '.. j The following lixamples illustrate the invention, without, | however, ih any way limiting it: Example 1. 2-(diethoxythiophosphoryloxy) pyrido [1,2a] pyrimidine 4-one : One mixes 40 g of 2-hydroxy pyrido [1,2a] pyrimidine 4-one (Ber. 1168, 1924), 34- g of potassium carbonate in 400 cm^ of acetone and 39 cm^ of diethyl chlorothiophosphate.
The suspension obtained is agitated for sixteen hours at ambient temperature, then brought for five hours to reflux.
After eliminating the mineral salts, one evaporates the solvent to dryness. The oil obtained is chromatographed on silica gel by eluting with a mixture of cyclohexane, acetone and chloroform (1-1-1). After evaporating the eluant, one obtains 19 g of 2-(diethpxythiophosphoryloxy) pyrido [1,2a] - pyrimidine 4-one in the form of white crystals melting at 82°C.
Analysis: 012H151*2 eliminates the mineral salts by vacuum filtering and one evaporates the solvent to dryness. One obtains a red oil which one pours into 300 cm^ of iced water. One vacuum filters and one washes with methanol the precipitate obtained* One dries it and one dissolves it in chloroform, then one filters it on magnesium silicate and one evaporates to dryness.
One thus obtains 9· 5 g of g^imethoxythiophosphorylox ) ^ pyrido Cl,2a] pyrimidine 4-one in the form of white crystals melting at 125°C. i Analysis : C-^N-^N^PS Calculated : C % 41.96 H % 3.88 N % 9.78. P % 10.82 Found : 41.9 . 4.1 9.6 11.0 Example 5. 2-(N-methyl O-ethylthiophosphoramidoxy) pyrido [1,2a] pyrimidine 4-one : One mixes 12 g of 2-hydroxy pyrido [1, 2a] pyrimidine 4-one and 10.3 g of potassium carbonate in 5°0 cm' of acetone. One agitates at ambient temperature for thirty minutes and one adds 13 g of ethyl N-methyl chlorothiophosphoramidate (C.A. 1601, 2828c-1964) and one brings to reflux for twenty-four hours. One vacuum filters the precipitate formed and one concentrates the solvent. One chromatographs on silica gel by eluting with a mixture of chloroform, acetone and cyclohexane (l-l-l). After evaporating the eluant, one obtains 1.5 g of 2-(N-methyl 0-ethyl thiophosphoramidOxy) pyrido [l,¾a] pyrimidine 4-one in the form of a cream-coloured crystallized solid, melting at 95°C» Analysis : C^H^N^PS Calculated : C % 44.29 H % 4.39 % 14.09 P % 10.38 Found : 44.2 4.8 13.8 10.3 Example 4. 2-(diethoxythiophosphoryloxy) 8-methyl pyrido .pyrimidine [1.2aJ/4-one : One mixes 17.6 g of 2-hydroxy 8-methyl pyrido [1,2a] 1 pyrimidine 4-one (J.*, Helv. Chem. 1967 , 1, 523) and 13.8 g of potassium carbonate in 400 cm' of acetone. One agitates for thirty minutes at ambient temperature and one adds 18.8 g> of Ο,Ο-diethyl chlorothiophosphate. One agitates for ' twenty-four hours at ambient temperature and one eliminates the mineral salts by vacuum filtering. One concentrates the solvent and one chromatographs the oil obtained on silica gel by eluting with a mixture of chloroform, . acetone and cyclohexane (1-1-1). After evaporating the eluant, one obtains an oil which one crystallizes in hexane. One vacuum filters and one obtains 11.8 g of 2-(diethoxythiophosphoryl- oxy) 8-methyl pyrido [1,2a] pyrimidine 4-one in the form of light yellow crystals melting at 75°C.
Analysis : C-^H^N^PS Calculated : C % 47. 56 H % 5.22 N % 8,53 P % 9. 3 Found : 7. 5.1 8.3 9.5 Example 5. 2-(dimethoxythiophosphoryloxy) 8-methyl pyrido [1,2a] pyrimidine 4-one i One mixes 17.6 g of 2-hydroxy 8-methyl pyrido [1,2a] pyrimidine 4-one and 13.6 g of potassium carbonate in 400 cm^ of acetone. One agitates for thirty minutes at ambient temperature and one adds 16 g of 0,0-dimethyl chlorothiophosphate. One agitates for twenty-four hours at ambient temperature and one eliminates the mineral salts by vacuum filtering. One concentrates the solvent and one chromatographs the residue on silica gel by eluting with a mixture of chloroform, acetone and cyclohexane (l-l-l). After evaporating the eluant, one obtains 6.2 g of 2-(dimeth xythiophosphoryloxy) 8-methyl pyrido [1,2a] pyrimidine 4-one in the form of yellow crystals melting at 110°C.
Analysis : ci i$!204E'S ; Calculated : C % 44.00 H % 4.36 1 N % 9.33 P % 10,31 Found : 44.0 4.4 9.0 10.3 Example 6. 2-(aiethoxythiophogphoryloxy) pyrimido. Cl«2a3 pyrimidine 4-one : ; One mixes 815 mg °f 2-hydroxy pyrimido [1,2a] pyrimidine 4-one (Monatshefte Chem. 1962, 34) and 690 mg of . potassium carbonate in 8 cur of acetone. One agitates for five minutes and one adds 940 mg of diethyl chlorothiopliosphate. One agitates for one night at ambient temperature and one brings to reflux for two hours. One filters and one evaporates the solvent to dryness. One obtains 600 mg of yellow oil which one chromatographs on silica gel by eluting with a mixture of chloroform, acetone and cyclohexane (l-l-l). After evaporating the eluant, one obtains 58 m j of 2-(diethoxythiophosphoryloxy) pyrimido [1,2a] pyrimidine ! 4-one, in the form of an oil. ' Analysis : C-^H-^N^PS Calculated : C % 41.90 H % 4.48 N % 13.33 P % 9.82 Pound : 42.1 ' 4.7 13.0 9.6 I i Example 7. 2-(diethoxythiophosphoryloxy) 3-methyl pyrido [1,2a] pyrimidine 4-one : One mixes 35 g of 2-hydroxy 3-methyl pyrido [1,2a] pyrimidine 4-one (Ber., 1168, 1924), 31 cnr5 of diethyl chlorothiophosphate and 27 g of potassium carbonate in 35P cm^ I of acetone. One agitates for sixteen hours at ambient ' temperature. One filters and one evaporates the filtrate to dryness. One obtains a red oil which one chromatographs on silica gel by eluting with a cyclohexane-ethyl acetate mixture (3*7)· After evaporating the eluant, one obtains .g of 2-(diethoxythiophosphoryloxy) 3-methyl pyrido [1,2a] pyrimidine 4-one in the form of yellow crystals meltin towards 78°C-80°C. 1 Analysis t O^H^gO^FS Calculated : C % 7- 56 H % 5-22 .., N % 8.55 P % 9.^5 Found : .7 5Λ 8.5 9.
Example 8. 2-(diethoxythiophosphoryloxy) 3-carbethoxy pyrido L"l, 2a3 pyrimidine -one : Stage_A : -hydrox^ 2~car eth^ One mixes 9·4 g of 2-aminopyridine and 23.2 g of tricarbethoxy methane. One heats the suspension obtained at 200°C until ethanol is no longer distilled. After cooling, one takes up the residue with acetone and one vacuum filters the crystals obtained. One obtains 15· 5 g of 2-hydroxy 3-carbethoxy pyrido [1 , 2a] pyrimidine -one, melting at 198°0.
I.R. Spectrum : li712cm-l Qa0 Ι,δβΟ0111"1 C=0 conjugated ester l,636cmrl C=C conjugated.
Stage__B : 2-^diethox^thiophosphorjl Clt2a] pyrimidine -one : One mixes 11.5 S of the product obtained in Stage A, 9»4 g of diethyl chlorothiophosphate and 7 g of potassium carbonate in 115 cur of, acetone. One agitates for sixteen hours at ambient temperature, and for three hours at reflux. After cooling, one filters and one evaporates the filtrate to dryness. One obtains an oil which one chromatographs on silica gel by eluting with a eyelohexane-ethyl acetate mixture (2-8). After evaporating i the eluant, one obtains 5 g of 2-(diethoxythiophosphoryloxy) 3-carbethoxy pyrido LI, 2a] pyrimidine -one in the form of yellow crystals melting at 105°C.
Analysis : C^H^gOgPS Calculated : C % 6.63 H % 4.96 .. N % 7.25 P % 8.01 Pound : 46.7 5.0 7.3 7- 9 Example 9. 2-(diethoxythiophosphoryloxy) 3-chloro pyrido [1.2a3 pyrimidine 4-one : S age_A : 2z≤-2-i2£2_2-hydro y_ jrido-[lJl2a^ : One heats at reflux for five hours a suspension of 45 S of 2-hydroxy pyrido 1.1 , 2a] pyrimidine 4-one and 37 g of N-chlorosuccinimide in 300 crn^ of acetic acid. One vacuum filters in the hot the solid obtained, then one rinses it with ether. One obtains 47 g of 3-chloro 2-hydroxy pyrido [1 , 2a] pyrimidine 4-one in the form of white crystals meltin at 325°C.
I.R. Spectrum : l^OO011^1 0.0 Stage_B : ϊίΐSi^ine_ -one : One mixes 30 g o the product obtained in stage A, 24 crn^ of diethyl chlorothiophosphate, 21.4 cm^ of triethylamine and 400 cnr of acetonitrile. One agitates for sixteen ojie. hours at ambient temperature. One filters and evaporates the filtrate to dryness. One dissolves the crystals obtained in a mixture of water and benzene. One separates the organic phase which one dries on sodium sulphate. After evaporating the benzene, one obtainp a crystallized product which one recrystallizes in 300 cm^ of an isopropyl ether -benzene mixture (8-2). One thus obtains 19 g of 2-(diethoxy- thiophosphoryloxy) 3-chloro pyrido [1,2a] pyrimidine 4-one in -the form of white crystals melting at 130°C.
Analysis : C-^H^Cl N^PS Calculated : C 41.32 H% 4.05 W/o 8.04 01% 10.17 8.89 Found : 41.7 4.1 8.0 10.3 8.9 Example 10. 2-(diethoxythiophosphoryloxy) 7-nitro pyrido [l«2a3 pyrimidine 4-one : S age_A : 2-hydroxy_7-nitro_ pyrido, One mixes, under agitation, 2.8 g of 2-amino ^ττάΧΈ pyridine and 10 g of trichlorophenyl malonate and one heats at 230°C for 15 minutes. One allows to cool and adds, at o -5 about 50 CfHQ cur of acetone. One allows to. cool to ambient temperature and vacuum filters the precipitate obtained.
One obtains 3·2 g of 2-hydroxy 7-nitro pyrido pyrimidine 4-one i the" ~¾ form of brown crystals melting at 320°C, with decomposition.
Analysis : Calculated^: C 46.35 H 2.43 N 20.28 Pound : 46.4 2.3 19.9 Stage_B : ^d^etho^thio os or^ One mixes 21 g of the product as it is obtained in stage A and 12 g of potassium terbutylate in 1 0 cm^ of methanol.
One agitates for 2 hours at ambient temperature and evaporates to dryness. The crystals obtained are dissolved in ether, vacuum filtered and put into suspension in 300 cm- of aoetonitrile. One adds to this suspension 17 cu5 of 0 ,0-diethyl chlorothiophosphate and one heats it at reflux for 20 hours. After cooling, one filters the reaction Λ mixture, evaporates the filtrate to dryness and take-s up the residue with 1 0 cm^ of a cyclohexara-ethyi acetate mixture 1,1. One vacuum filters the precipitate and the filtrate is chromatographed on silica by eluting with a cyclohexane-ethyl acetate mixture 6-4. One thus obtains 3.9 g of 2-(diethoxythiophosphoryloxy) 7-nitro pyrido [1,2a] pyrimidine 4-one in the form of brown crystals melting at 9 °C.
Analysis : C^H-^ ^PS Calculated^: C 40.12 H 3.95 N 11.69 P 8.63 Pound : 0. 3-9 11.9 8.6 Example 11 : Study of the insecticidal activity of 2-(dimethoxy-thiophosphoryloxy) pyrido [1,2a] pyrimidine 4-one (compound A) and 2-(die hoxythiophosphoryloxy) pyrido [1,2a] pyrimidine 4-one (compound B) : A/ Test on Aphis fabae (contact ingestion) ; Broad. , bean plants about 15 cm high, are used and the test insect is Aphis fabae. 4 cm^ of aqueous suspension of the product to be tested s employed, which is sprayed onto each broad bean plant, f Contamination is carried out with about twenty wingless a.phids. There are two. repetitions per treatment. 1 , They are kept with lighting, at 20°C and with 50% relative humidity.
The control of percentage mortality is carried out two hours, twenty-four hours and forty-eight hours after treatment.
The experimental results obtained with compound A are summarized in the following table (results expressed in percentage mortality) : Doses in p.p.m. of 1Q0 10 1 active material 2 hours 51 ' 0 0 24 hours 100 80 0 48 hours 100 100 0 Conclusion : compound A is endowed with interesting insecticidal activity with regard to Aphis fabae.
B/ Test on noctua (ingestion) : Prodenia litura caterpillars are Used. 8 mm diameter circles, cut from lettuce leaves, are introduced into closed plastic boxes. 4 μΐ of acetonfc solution of the product to he tested are put per circle of leaf. 15 caterpillars per treatment (caterpillars aged 10 days on average) are used. The animals are left at 20°C in natural light with a relative humidity of 50%. The individuals are fed after they have consumed the treated lozenge. Controls are carried out one hour, twenty-four hours and forty-eight hours after treatment, ] .
The experimental results obtained with compound B, expressed in percentage mortality, are summarized in the following table: Conclusion : compound B is endowed with interesting insecticidal activity with regard to Prodenia litura caterpillars, C/. Test on adult Musca domestica (micro-contact) : Using an Arnold micro-applicator, 1 μΐ of acetonic solution of the product to be tested is placed on the, dorsal thorax of each insect, previously anaesthetized with ether. The test is carried out on 50 insects per concentration and with concentrations of the products to be tested, equivalent to 1,000, 500, 20 and 100 p.p.m. The results obtained are measured twenty-four hours after treatment, the animals having been fed during this time.
Compound B gives the following results, expressed in percentage mortality: Conclusion : compound B is endowed with interesting insecticidal activity with regard to Musca domestica. . ; D/ Test on adult drosophila (Drosophila melanogaster) : This test measures the activity with vapour. It consists in placing the insects in a Petri dish, connected by a tergal gauze to a crystallizer of the same diameter, in which is put the compound to be tested, in acetonic the solution, which is evaporated before introducing/insects.
Three tests per concentration; are carried out and there are 25 individuals per concentration (adults of less than forty-eight hours). The results are expressed in percentage mortality at the end of four hours.; then twenty-four hours ' Cwith reference to non-treated controls) · The following table summarizes the experimental results obtained with compound B : >'; Conclusion : compound B is endowed with interesting insecticidal activity with regard to Drosophila melanogaster, E/ Test on cockroach : . .
This test is carried out by micro-contact. Cockroaches selected according to the criterion of length receive a micro* litre of acetonic solution between the second and third pairs of legs. After treatment, the "test insects" are kept in dim light at 20°C. Controls are carried out twenty-four hours, forty-eight hours, then five days after treatment,.
The experimental results obtained with compound B and expressed in percentage mortality are summarized in the ! , following table: I G Test on Tribolium confusum : The test is similar to that used for Sitophilus granarius (topical application test). Controls are carried out 5 days after treatment.
The experimental results obtained with compound B and expressed in percentage mortality are summarized in the 'ioliowin table : Conclusion : compound B is endowed with interesting insecticidal activity with regard to Tribolium confusum.
H/ Test on Carpocapsa pomonella : For this test apples are used on each of which cnr - of aqueous solution of the product to be tested are sprayed.
The concentrations of the products to be tested are of 1 , 500 and 7 Ο p.p.m. and ten apples per concentration are .used. Then, on each apple are placed 10 to 15 eggs of Carpocapsa pomonella ready to hatch out, and at the end of 14 days the number of undamaged fruit is evaluated. It .was established that with the concentrations used all the Ifruits were undamaged; compound B is therefore endowed with interesting insecticidal. activity with regard to 7 Carpocapsa pomonella. 1/ Teat on adult Oeratitle capitatat then at the end of five days.
The results obtained with compound B are the following: Conclusion : compound B is endowed with interesting insecticidal activity with regard to Ceratitis capitata, , · , Example 12 : Study of the nematocidal activity of 2-(diethoxy- thiophosphoryloxy) pyrido Cl, 2a3 pyrimidine 4-one (compound B) ' Soil infested with Melo'idogynus S.p.p. is- used, being placed in plastic sacks of about 3 litres' volume.
Nematocidal treatments being considered as efficacious ',· down to a depth of 30 cm, a 3 litres' volume of soil corresponds tc an area of 100 cm^, or 10"*^ ha (since 100 cm^ x 30 cm! - 3 ,000 cm , or 3 litres). Each volume of infested soil ! receives 100 cur of aqueous suspension containing 0^250 g of compound B (which corresponds to 250 kg/ha) . The controls receive 100 cm^ of water. The plastic sacks containing the soil are closed immediately after treatment, then shaken so as to obtain good distribution of the product. .' ' Two weeks after treatment, the sacks are opened and the ;■■ soil' which is contained in them serves for transplantin tomato plants (St. Pierre variety) into different pots.
Two months after transplanting, the number of galls existing on the roots is counted; there is, in fact, a relation between the population of Meloidogynes in each pot and the number of galls.
The results obtained with compound B, compared with a control, are summarized in the following table: · Conclusion : compound B is endowed with good nematocidal activity with regard to Meloidogynus S.p.p.
Example 13. Study of the acaricidal activity of 2-(dimethoxythio-» phosphoryloxy pyrido Cl,2a3 pyrimidine -one (compound A) and of 2-(diethoxythiophosphoryloxy) pyrido Cl«2a] pyrimidine -one (compound B) : A) Ovicidal test Bean leaves infested with 10 females of Tetranyehus urticae per leaf and smeared with glue on their peripheries are used; .the females are allowed to lay for twenty-four hours then they are removed from the leaves. The leaves infested with eggs are divided into two groups: |1 . a) the first group is treated with compound B; work is carried' out by spraying 2.5 ml of aqueous solution of compound B on each leaf at concentrations of 0 and 10 mg per litre. Four · leaves per concentration are used. b) the second group oi? control group is not treated, A count of live eggs takes place 9 days after the beginning of the treatment. The results expressed in percentage mortality of the eggs are summarized in the following table: , B) Test for killing adults t .
Bean leaves infested with 25 adults of Tetranychus urticae per leaf and smeared with glue at their peripheries are used. The infested leaves are divided into three groups:, a) the first two groups are respectively treated by ' Λ spraying with 2.5 ml of an aqueous solution of compounds A or; B ,£t concentrations of ur leaves per concentratio b) the third group or control group is not treated, A count of live acarida takes place forty-eight hours after spraying. The results, expressed in percentage mortality* , are summarized in the following table: Conclusion : compounds A and B are endowed with interesting acaricidal properties.

Claims (11)

WHAT IS CLAIMED IS:
1. ) The organo-phosphorus derivatives of formul a I : In which R-j represents a methlne group (^CH-) or a nitrogen atom, R*2 represents a hydrogen atom, an alkyl radical having from 1 to 3 carbon atoms or the NO2 radical , R3 represents a hydrogen atom, a straight or branched al kyl radical having from 1 to 3 carbon atoms, a chlorine or bromine atom, an al kyl -oxycarbonyl group 1n which the al kyl radical contains from 1 to 3 carbon atoms, R represents a strai ght or branched al kyl radical containing from 1 to 3 carbon atoms, R5 represents an al koxy radical .containing from 1 to 3 carbon atoms, or an amine grouping - ^ , 1n which R represents a straight or branched alkyl radical containing from 1 to 3 carbon atoms .
2. ) The organo-phosphorus derivatives of formula I ' : in which R1 represents a methine group (=»CH-) or a nitrogen atom, R2 represents a hydrogen atom or an al kyl radical having from 1 to 3 carbon atoms, R? represents a hydrogen atom, a straight or branched al kyl radical haying from 1 to 3 carbon atoms , a chlorine r bromine atom, an al kylo^ycarbonyl group In which al kyl radical contains from 1 to 3 carbon atoms, R4 represents a straight or branched al kyl radical containing from 1 to 3 carbon atoms , R5 represents an a koxy radical containing R represents a straight or branched alkyl radical containing from 1 to 3 carbon atoms .
3. ) 2-(d1ethoxyth1ophosphorylo*y) pyrido [1 ,2a] pyrimldine 4-*one,
4. ) 2-(d1metho yth1ophosphorylo*y) pyrldo [1 ,2a] pyHmldlne 4-one,
5. ) A process for preparing the products of formula I as defined in claim 1 , characterized In that a compound of formula II : in which R-j , R'g and R3 have the meaning already Indicated is reacted with a halogenophosphate of formula III : ,in which Hal represents a chlorine or bromine atom and R^ and Rc have the meaning already indicated, in the presence of' a hydracid acceptor.
6. ) A process for preparing the products of formula I' as defined in claim 2, characterized in that a compound of formula II : in which R^, Eg and ^ have the meaning already indicated is reacted with a halogenophosphate of formula III : in which Hal represents a chlorine or bromine atom and ^ and R^ have the meaning already indicated, in the presence of a hydracid ' acceptor.
7. ) Pesticidal compositions containing as active material one. at least, of the compounds of formula I as defined in claim 1.
8. ) Pesticidal compositions containing as active "material one, at least, of the compounds of formula I' as defined in claim 2.
9. ) Insecticidal or nematocidal compositions containing as : active material one; at least, of the compounds of formula 'ΐ' as defined in claim 2.
10. ) Compositions according to claim 8 in which the active material is constituted by the compound of claim 3.
11. ) Compositions according to claim 8 in which the active] material is constituted by the compound of claim 4·.
IL43034A 1972-09-11 1973-08-21 Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them IL43034A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7232088A FR2198697B1 (en) 1972-09-11 1972-09-11

Publications (2)

Publication Number Publication Date
IL43034A0 IL43034A0 (en) 1973-11-28
IL43034A true IL43034A (en) 1976-05-31

Family

ID=9104093

Family Applications (1)

Application Number Title Priority Date Filing Date
IL43034A IL43034A (en) 1972-09-11 1973-08-21 Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them

Country Status (20)

Country Link
US (1) US3904624A (en)
JP (1) JPS5648481B2 (en)
BE (1) BE804654A (en)
BR (1) BR7306999D0 (en)
CH (1) CH575430A5 (en)
DD (1) DD109316A5 (en)
DK (1) DK138899B (en)
ES (1) ES418627A1 (en)
FR (1) FR2198697B1 (en)
GB (1) GB1408718A (en)
GT (1) GT198065690A (en)
HU (1) HU168852B (en)
IL (1) IL43034A (en)
IT (1) IT1047946B (en)
NL (1) NL7312432A (en)
OA (1) OA04553A (en)
SU (2) SU507246A3 (en)
TR (1) TR18108A (en)
YU (1) YU36304B (en)
ZA (1) ZA735709B (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2703712A1 (en) * 1977-01-29 1978-08-03 Bayer Ag SUBSTITUTED PYRIMIDINONE ANGLE CLAMP ON (DI) -THIO ANGLE CLAMP ON -PHOSPHORUS- (PHOSPHONE) -ACIDESTER OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES
US4395551A (en) * 1981-12-10 1983-07-26 Uniroyal, Inc. Pyridopyrimidinone compounds
US4472389A (en) * 1981-12-10 1984-09-18 Uniroyal, Inc. Substituted pyrimidinyl organophosphorus insecticides
US4634690A (en) * 1981-12-10 1987-01-06 Uniroyal Chemical Company, Inc. Substituted pyrimidinyl organophosphorus insecticides
JPS60125077U (en) * 1984-01-30 1985-08-23 織田　義男 Nailing support
JP2532677Y2 (en) * 1991-03-13 1997-04-16 株式会社 日本バノック Lashing device
US5877178A (en) 1991-04-08 1999-03-02 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
WO1992017478A1 (en) * 1991-04-08 1992-10-15 Duquesne University Of The Holy Ghost 5-ALKYL-6-[[AMINO]METHYL]PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AND METHODS OF PREPARING AND USING THESE DERIVATIVES
US5939420A (en) 1991-04-08 1999-08-17 Duquesne University Of The Holy Ghost Pyrrolo 2,3d!derivatives
US5346900A (en) * 1991-04-08 1994-09-13 Duquesne University Of The Holy Ghost 5-alkyl-6-[[amino]methyl]pyrido[2,3-D]pyrimidine derivatives and methods of using these derivatives
US5508281A (en) * 1991-04-08 1996-04-16 Duquesne University Of The Holy Ghost Derivatives of pyrido [2,3-d] and [3,2-d] pyrimidine and methods of using these derivatives
US6962920B2 (en) 1992-09-23 2005-11-08 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US6537999B2 (en) 1996-06-06 2003-03-25 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US6106033A (en) * 1997-08-26 2000-08-22 Ewald Witte Gmbh & Co. Kg Catch-hook arrangement for a front hood or the like on motor vehicles
IN2014DN10069A (en) * 2012-06-19 2015-08-14 Dow Global Technologies Llc

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1239695B (en) * 1964-12-24 1967-05-03 Bayer Ag Process for the preparation of phosphorus, phosphonic, thionophosphorus or thionophosphonic acid esters
BE788828A (en) * 1971-09-16 1973-03-14 Roussel Uclaf NEW HETEROCYCLIC ORGANOPHOSPHORUS DERIVATIVES AND PROCESS OF PREPARATION

Also Published As

Publication number Publication date
DE2345762A1 (en) 1974-03-21
TR18108A (en) 1976-09-30
YU36304B (en) 1982-06-18
HU168852B (en) 1976-07-28
FR2198697A1 (en) 1974-04-05
YU240473A (en) 1981-08-31
JPS4992096A (en) 1974-09-03
FR2198697B1 (en) 1975-09-12
IL43034A0 (en) 1973-11-28
DK138899C (en) 1979-04-23
CH575430A5 (en) 1976-05-14
OA04553A (en) 1980-04-30
JPS5648481B2 (en) 1981-11-16
US3904624A (en) 1975-09-09
DD109316A5 (en) 1974-11-05
IT1047946B (en) 1980-10-20
DE2345762B2 (en) 1977-04-21
GT198065690A (en) 1982-03-27
SU507246A3 (en) 1976-03-15
DK138899B (en) 1978-11-13
GB1408718A (en) 1975-10-01
ES418627A1 (en) 1976-02-16
ZA735709B (en) 1974-10-30
SU733504A3 (en) 1980-05-05
NL7312432A (en) 1974-03-13
BE804654A (en) 1974-03-11
BR7306999D0 (en) 1974-06-27

Similar Documents

Publication Publication Date Title
IL43034A (en) Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them
US2908605A (en) New organic phosphorus compounds and process for their manufacture
US3857838A (en) Organophosphate ester derivatives of heterocyclic compounds and process
HU186981B (en) Pesticide compositions containing alkyl-thio-phosphate with alpha-branching as active substance and process for preparing the active substances thereof
KR870000643B1 (en) Process for the preparation of oxime-phosphate compounds
US3248412A (en) Thiophosphonic acid esters
US3733376A (en) Phosphoric acid esters
US4000267A (en) Insecticidal and acaricidal compositions employing pyrido[1,2a]pyrimidinone thiophosphates
US4020076A (en) Novel phosphoryloxy-thiazoles
US3301749A (en) Pesticidal omicron, omicron-dimethyl-omicron-(2-[or 3-] methoxy-4-cyanophenyl) phosphorothioate
US3265773A (en) Alkoxymethylenamides of omicron, omicron-dialkylthio-or omicron, omicron-dialkyl-dithiophosphorylacetic acids
US3801577A (en) Phosphoric and thiophosphoric acid derivatives of quinoxaline
IL32639A (en) Heterocyclic thio-or dithio-phosphoric acid esters,their manufacture and use as pesticides
US4128562A (en) Novel 3-(phosphoryloxy) and (phosphonyloxy)-thiophenes
US3886274A (en) Control of animal pests with 3H-oxazol-{8 4,5-6{9 pyridine-2-one esters of 3-(-o-)or (-s-)-0,0{40 di(lower alkyl) phosphates and thiophosphates
US3808218A (en) 3h-oxazolo(4,5-b)pyridine-2-one,esters with 3-(-o-)or(-s-)-o,o'-diloweralkyl phosphates or thiophosphates
HU176606B (en) Insecticide,acaricide and nematocide preparations containing new thiophene-phosphor derivatives and process for preparing the nctive substance thereof
US3929809A (en) Oxazolo-{8 4,5-b{9 -pyridine-2-ones and -2-thiones as intermediates
EP0224217B1 (en) Phosphoric acid derivatives, process for their preparation and their use for combatting pests
US3445484A (en) Organic phosphorus compounds
US2943015A (en) Omicron:omicron'-diethyl s-(beta-dimethyl amino-beta-methyl)-propyl phosphorothiolates and pesticidal compositions containing same
US3390209A (en) Sulfur containing diphenylene diphosphates
US3284546A (en) Thiophosphoric esters
US3830884A (en) Dialkylsulfoximinocarbonylmethyl thiophosphates and process for preparation thereof
US3931175A (en) Imidazo(1,2b)pyridazinyl esters, process and insecticidal compositions