IL40323A - Substituted pyrimidone organophosphorous derivatives and process for preparation - Google Patents
Substituted pyrimidone organophosphorous derivatives and process for preparationInfo
- Publication number
- IL40323A IL40323A IL40323A IL4032372A IL40323A IL 40323 A IL40323 A IL 40323A IL 40323 A IL40323 A IL 40323A IL 4032372 A IL4032372 A IL 4032372A IL 40323 A IL40323 A IL 40323A
- Authority
- IL
- Israel
- Prior art keywords
- pyrrolo
- insecticidal
- pyrimidone
- carbon atoms
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 5
- 150000008318 pyrimidones Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 230000000749 insecticidal effect Effects 0.000 claims description 7
- 239000011149 active material Substances 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000005947 Dimethoate Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 229960005286 carbaryl Drugs 0.000 description 2
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 2
- MHCWWALYKYDTHV-UHFFFAOYSA-N dihydroxyphosphinothioyl hypochlorite Chemical compound OP(O)(=S)OCl MHCWWALYKYDTHV-UHFFFAOYSA-N 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 235000019695 salad leaves Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 description 1
- NLCIYDBRSJQKTO-UHFFFAOYSA-N chloroform;cyclohexane;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.C1CCCCC1 NLCIYDBRSJQKTO-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- MSQDVGOEBXMPRF-UHFFFAOYSA-N cyclohexane;propan-2-one Chemical compound CC(C)=O.C1CCCCC1 MSQDVGOEBXMPRF-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000020573 organic concentrate Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- DXVAQZJPPDWTNY-UHFFFAOYSA-N pyrrolo[3,2-d]pyrimidin-2-one Chemical compound O=C1N=CC2=NC=CC2=N1 DXVAQZJPPDWTNY-UHFFFAOYSA-N 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
New substituted pyrimidone organophosphorous derivatives and process for preparation New organophosphorous derivatives and process for preparation phosphate of general formula III in which Hal represents a chlorine atom or a bromine and have the aforesaid In a preferred method of one uses a phosphate as halogenophosphate of general formula The condensation reaction is carried out in an organic solvent such as methanol or ethyl in the presence of a basic agent such as an alkali metal carbonate or an alkali metal or in the presence of an organic base such as trimethylamine for the compounds of formula represents a hydrogen represents an radical and represents an alkoxy one can prepare these compounds by reacting a compound general formula with a trialkyl The invention also includes the insecticidal acaricidal compositions containing as active material at least one of the compounds of formula These compositions can take the form of containing the active for example in a mixture with a vehicle cationic surface active a uniform dispersion of the substances of the The vehicle used can be a liquid such as hydrocarbons or other organic a animal or vegetable or a powder such as silicates preferably contain from 10 to of active material by The acaricidal liquids or powders for foliar pulverisation contain preferably from 20 to of active material by As insecticidal composition one will use for an emulsifiable concentrate containing by weight of pyrrolo of triglyceride combined with a acid of Atlox 855 triglyceride combined with a indice of The invention also includes a process for insecticidal acaricidal characterized in to this end one uses a composition containing as active material at least one of the compounds of general formula optionally admixed with one or several other pesticidal The compounds of general formula used as starring material in the process of the can be prepared according to a process analogous to that described by Berre and Renaut The azepino is described by Glushkov and Magidson The thiazolo is described by Dashkevieh 3723 Certain compounds of formula II are not described in the These are pyrido pyrrolo and whose preparation is given further on for information in the experimental can prepared by the with the compounds of general formula The following examples illustrate the invention without however limiting Preparations One introduces of sodium into 300 of after the sodium has 19 of pyridine hydrochloride and of ethyl takes the reaction mixture to keeps it there for 16 removes the insoluble matter formed by concentrates to adds acidifies to by adding an aqueous solution of hydrochloric isolates the precipitate formed by filtering and obtains of 1 pyrido Spectrum absorption at 1709 and 1606 corresponding to absorption at 1587 corresponding to absorption at corresponding to ethyl thio heats this mixture to keeps at this temperature for 15 crushes the residue obtained in the presence of isolates the resulting powder by filtering and obtains 31 of thio 7 dihydro 1 pyrrolo One introduces 60 of pyrrolo into 400 of one then duces 22 of sodium keeps under agitation till the o temperature comes back to 20 removes the precipitate formed by evaporates the filtrate to takes up with triturates isolates by 88 of hydroxy 7 pyrrolo sodium ro One introduces 88 of pyrrolo sodium salt and 63 of ethyl thiophoaphoramido chloridate into of one takes to reflux for 33 removes the precipitate formed by evaporates the filtrate to dryness and obtains 100 of a oil which one chromatogrephs on eluting with a cyclohexane acetone chloroform so as to obtain yellowish crystals which one purifies by washing with essence G one thus obtains of thiophoaphoramido pyrrolo melting at Analysis i 2 Calculated Found Example 4 hoxy thiophoaphoryl thiazolo One introduces of thiazolo and 28 gi of potassium carbonate into a solution of 35 of chlorothiophosphate in 300 of One takes the solution thus obtained to reflux for 16 cy o exane e y ace a one o tains 19 of thiazolo n Analysis Calculated C I Found Example 5 dihydro pyrrolo One introduces of pyrrolo into a suspension including of chlorothiophosphate and of potassium carbonate in 10 of the suspension obtained is agitated for 8 one removes the insoluble matter by evaporates the filtrate to dryness and obtains a grey oil which one chromatographs on silica eluant ethyl afietate One obtains 406 of pyrrolo melting at Analysis Calculated Found Example 6 dihydro pyrrolo One introduces at of pyrrolo and of sodium methylate into 400 of One agitates the solution obtained for 15 minutes at ambient temperature and evaporates to The crystals obtained are triturated in then isolated by thus obtains 134 of hydroxy pyrrolo One introduces of crude sodium salt obtained in Stage into a solution including 0 phate in cc One takes to reflux for 36 removes the precipitate formed by and evaporates the filtrate to One obtains a red oil which one chrpmatographs on silica acetone One obtains a yellow oil which one graphs once again on silica eluant ethyl One thus obtains 20 of 1 pyrrolo n Analysis Calculated Found Example pyrfLmidone One introduces of pyrlmidone 2 according to the method of Schdbert et Annalen der Chemie 91 21 potassium carbonate and chloro thiophosphate in 25Ο of One takes to reflux for 3 removes the formed by evaporates the filtrate to dryness then crystallizes by adding One obtains yellow crystals which one chromatographs on silica cyclohexane chloroform One thus obtains 20 1 of thiophosphoryloxy 2 meltin at Analysis Calculated Found Example 8 and ethyl acetate and 3 Analysis 5 Calculated Found Example 11 pyrrolo One introduces 41 of pyrrolo 400 topanol and 5 of potassium carbonate into a mixture of 300 of acetone and 30 of adds 40 of chloro takes the reaction mixture to keeps it there for one hour and 45 concentrates to dryness by distillation under reduced adds extracts with ethyl dries the organic concentrates it to dryness by distillation under reduced crystallizes the residue in ether and obtains 23 of pyrrolo Analysis Calculated Pound Example 12 thiazolo One introduces 12 of thiazolo of potassium carbonate into 200 of introduces of chloro agitates for 64 hours at ambient removes the mineral salts by concentrates to dryness by distillation under reduced the residue on silica eluting with a cyclohexane and ethyl acetate and obtains 8 of agitates 16 hours at ambient one then takes the reaction mixture to keeps it this temperature for one hour and JO removes the mineral salts concentrates the filtrate to chromatographs the residue on eluting with a cyclohexane and ethyl acetate mixture and obtains 9 of pyrido Analysis Calculated Found Example 16 pyrrolo One introduces of pyrrolo and of potassium carbonate into 300 of takes this mixture to keeps it there for one cools to adds of chloro takes the reaction mixture to keeps it at this temperature for 4 removes the insoluble matter formed by concentrates to dryness under reduced chromatographs the residue on silica gel eluting with a ohloroform and acetone mixture and obtains of pyrrolo Analysis Calculated Found Example 17 pyrrolo One introduces of pyrrolo and of potassium carbonate into 400 of agitates for one hour at ambient temperature Analysis Calculated B Example 20 sopropyloxy thiophosphoryloxy pyrrolo One introduces of 7 pyrrolo and 9 of potassium carbonate into a mixture of of acetone and of adds 15 of isopropyl chloro takes the reaction mixture to keeps it there for 6 hours end One evaporates the solvents under reduced adds extracts with ethyl dries the ethereal concentrates it to chromato raphs the residue on silica eluting with a cyclohexane acetone and chloroform mixture and obtains 10 of pyrrolo Analysis Calculated Found Example 21 C I pyrrolo One introduces of pyrrolo and of potassium carbonate into a mixture of 150 of acetone and 20 of adds 15 of di chloro takes the reaction mixture to reflux keeps it there for 5 concentrates to adds extracts with dries the ethereal concentrates to dryness chromatographs the residue on silica eluting with a chloroform and acetone mixture and obtains 11 of pyrrolo pyrimidone y ro a pyrro o m done One introduces 31 of thio dihydro pyrrolo of potassium carbonate and of chloro thiophosphate into of agitates for 60 hours at ambient removes the mineral salts by concentrates to chromato raphs on silica eluting with a acetone and chloroform crystallizes in ether and obtains 6 of thio pyrrolo Analysis Calculated s C Found A Study of the insectlcidal properties of pyrrolo called compound A in the One uses bean plants which one divides into 3 groups The first group of plants is treated with compound one pulverises 1 ml of solution containing 5 of compound A per litre on each infests each leaf with 20 green fly and surrounds each leaf with gauze so as to prevent the green from The second group of plants is treated in the same way as the group of plants in group replacing compound A by dimethoate or dimethyl The third group of plants or control group is not one infests each leaf directly with 20 green One carries out counting off of the live insects and of those killed by the two the activity of compound A and that of dimethoate are expressed in a percentage of the reduction in the number of live The results are 5 5 1 Conclusion Compound A has very good activity with Ceratitia One uses salad leaves which one cuts up into pieces of 8 in one places each piece in a box at a rate of 1 piece per box and divides the boxes into groups The pieces of salad leaves in the boxes in group are treated with compound A at a rate of 4μ1 of aqueous solution of compound A on each piece and with the solutions including 000 250 and 625 of compound A per One operates in the same manner for group replacing compound A with carbaryl or 1 One places nothing on the pieces of leaves in group In each box of groups and one places a One counts the caterpillars which are still alive and those killed by the two insecticides at different intervals in The activity of compound A and that of carbaryl are expressed in percentage the reduction in number of live The results are summarized in the following table rne xoy op pyrrolo This test is carried out by Cockroach grubs according to length receive a of acetonic solution pf the product to be tested between the second and pair of After treatment the are stored in dim light at and are The tests are carried out hours 48 hours then days after The experimental expressed in percentage of the are summarized in the following table Test on M sea This test is carried out by Plies receive a of acetonic solution of the product to be on the dorsal after having been put to sleep with The insects are stored at and of relative One feeds them with milk or The tests are carried out hour then 24 hours after The experimental results expressed in percentage of the mortality are summarized in the following table 500 5OO 1 hour 96 30 a a One carries out a test by ingestion contact with After pulverisation of the solution of the product to be one proceeds with infesting at a rate of 20 wingless individuals per bean The bean plants are surrounded with gauze so as to prevent the green One carries out counting of the living and the dead depending on the results are expressed in percentage of Abbott efficiency account of the control The following are the results obtained est The test is carried out on the prodenia litura It is made by The acetonic solution of the product to be test is deposited on salad disks of 6 in diameter which are placedin closed plastic boxes of One uses 15 caterpillars per treatment aged 10 days on The caterpillars are stored at and 50 relative humidity and are The tests are carried out one 24 hours and 48 hours after The experimental results expressed in a percentage of are summarized in the following table insufficientOCRQuality
Claims (1)
1. from, 1 to 3 carbon atoms, &2 represents a straight or branched alkyl radical containing from 1 to 3 carbon atoms, an alkoxy radical containing from 1 to 3 carbon atoms or an amino group similar or different represent ight or branched alkyl radical containing from 1 to 3 carbon atoms. 3) The 2-(diethoxy thiophosphoryloxy) 3-bromo [6H] 7,8-dihydro [1,2a] pyrrolo 4-pyrimidone. 7) ThQ 2-(methoxy ethoxy thiophosphoryloxy) [6H] 7»8-dihydro [1,2a] pyrrolo 4-pyrimidone . 8) The 2-(dipropyloxy thiophosphoryloxy) [6H] 7,8-dihydro [1,2a] pyrrolo 4-pyrimidone. "f 40323/2 14) A process for preparing the compounds according to Claim 1), for which Y' represents hydrogen, "^ represents an alkyl radical and R"2 represents and alkoxy radical, characterized 1n that one reacts a compound of general formula: with a trial kyl pho 15) The Insecticidal and/or acaricidal compositions containing as active material at least one of the compounds according to Claim I). 16) The insecticidal and/or acaricidal compositions containing as active material at least one of the compounds according to Claim 2). 17) A process for insecticidal and/or acaricidal control s characterized in that to control the insects and/or acarids there is applied an effective quantity of a composition according to Claim 15). 18) A process for insecticidal and/or acaricidal control, characterized in that to control the 1nse/c†:s and/or acarids there 1s applied an effective quantity of a composition according to Claim 16). Box 33116, Tel Aviv Attorneys for Applicant
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7133434A FR2152469B1 (en) | 1971-09-16 | 1971-09-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40323A0 IL40323A0 (en) | 1972-11-28 |
| IL40323A true IL40323A (en) | 1976-03-31 |
Family
ID=9083063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40323A IL40323A (en) | 1971-09-16 | 1972-09-07 | Substituted pyrimidone organophosphorous derivatives and process for preparation |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3857838A (en) |
| JP (1) | JPS4836189A (en) |
| AU (1) | AU466846B2 (en) |
| BE (1) | BE788828A (en) |
| CA (1) | CA981671A (en) |
| DE (1) | DE2245386A1 (en) |
| ES (1) | ES406728A1 (en) |
| FR (1) | FR2152469B1 (en) |
| GB (1) | GB1396169A (en) |
| IL (1) | IL40323A (en) |
| IT (1) | IT965384B (en) |
| NL (1) | NL7212526A (en) |
| ZA (1) | ZA726212B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198697B1 (en) * | 1972-09-11 | 1975-09-12 | Roussel Uclaf | |
| US4000267A (en) * | 1972-09-11 | 1976-12-28 | Roussel-Uclaf | Insecticidal and acaricidal compositions employing pyrido[1,2a]pyrimidinone thiophosphates |
| US3973009A (en) * | 1974-05-06 | 1976-08-03 | Stauffer Chemical Company | Insecticidal and miticidal method |
| 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 |
| DE3930130A1 (en) * | 1989-09-09 | 1991-03-21 | Boehringer Mannheim Gmbh | NEW AMIDINE GROUP-CONTAINING DIPHOSPHONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| JP2000026465A (en) * | 1998-07-14 | 2000-01-25 | Fuji Photo Film Co Ltd | Pyrrolo[1,2-a]pyrimidine and thermally sensitive recording material using the same |
| EP4241861A3 (en) * | 2017-02-15 | 2024-01-03 | ZURU (Singapore) Pte. Ltd. | Apparatus for housing and revealing a plurality of children's toys |
Family Cites Families (1)
| 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 |
-
0
- BE BE788828D patent/BE788828A/en unknown
-
1971
- 1971-09-16 FR FR7133434A patent/FR2152469B1/fr not_active Expired
-
1972
- 1972-09-07 IL IL40323A patent/IL40323A/en unknown
- 1972-09-12 US US00288393A patent/US3857838A/en not_active Expired - Lifetime
- 1972-09-14 JP JP47091865A patent/JPS4836189A/ja active Pending
- 1972-09-15 DE DE2245386A patent/DE2245386A1/en active Pending
- 1972-09-15 ES ES406728A patent/ES406728A1/en not_active Expired
- 1972-09-15 GB GB4282572A patent/GB1396169A/en not_active Expired
- 1972-09-15 AU AU46740/72A patent/AU466846B2/en not_active Expired
- 1972-09-15 NL NL7212526A patent/NL7212526A/xx not_active Application Discontinuation
- 1972-09-15 CA CA151,877A patent/CA981671A/en not_active Expired
- 1972-09-15 IT IT52790/72A patent/IT965384B/en active
-
1973
- 1973-09-12 ZA ZA726212A patent/ZA726212B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2152469A1 (en) | 1973-04-27 |
| JPS4836189A (en) | 1973-05-28 |
| BE788828A (en) | 1973-03-14 |
| IL40323A0 (en) | 1972-11-28 |
| US3857838A (en) | 1974-12-31 |
| IT965384B (en) | 1974-01-31 |
| NL7212526A (en) | 1973-03-20 |
| ES406728A1 (en) | 1975-10-01 |
| AU466846B2 (en) | 1975-11-13 |
| DE2245386A1 (en) | 1973-03-22 |
| GB1396169A (en) | 1975-06-04 |
| AU4674072A (en) | 1974-03-21 |
| ZA726212B (en) | 1973-10-31 |
| FR2152469B1 (en) | 1974-03-29 |
| CA981671A (en) | 1976-01-13 |
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