US3904624A - Pyrido(1,2a)pyrimidinone thiophosphates - Google Patents

Pyrido(1,2a)pyrimidinone thiophosphates Download PDF

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Publication number
US3904624A
US3904624A US394078A US39407873A US3904624A US 3904624 A US3904624 A US 3904624A US 394078 A US394078 A US 394078A US 39407873 A US39407873 A US 39407873A US 3904624 A US3904624 A US 3904624A
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Prior art keywords
pyrido
pyrimidine
compound
carbon atoms
mixture
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Expired - Lifetime
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US394078A
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English (en)
Inventor
Jacques Perronnet
Laurent Taliani
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Sanofi Aventis France
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Roussel Uclaf SA
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Priority to US05/589,466 priority Critical patent/US4000267A/en
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    • 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

Definitions

  • R is selected from the group consisting of methine and nitrogen
  • R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and N0
  • R is selected from the group consisting of hydrogen, straight or branched alkyl of l to 3 carbon atoms, chlorine, bromine, alkoxycarbonyl of 2 to 4 carbon atoms, phenyl and thioalkyl of 1 to 4 carbon atoms
  • R is branched or straight chain alkyl of l to 3 carbon atoms and R, is selected from the group consisting of straight and branched chain alkyl of 1 to 3 carbon atoms, alkoxy of l to 3 carbon atoms and wherein R and R are individually selected from the group consisting of hydrogen and branched and straight chain alkyl of 1 to 3 carbon atoms having pesticidal properties and their preparation.
  • R is selected from the group consisting of methine and nitrogen
  • R is selected from the group consisting of hydrogen, alkyl of l to 3 carbon atoms and N 0
  • R is selected from the group consisting of hydrogen, straight or branched alkyl of l to 3 carbon atoms, chlorine, bromine, alkoxycarbonyl of 2 to 4 carbon atoms, phenyl and thioalkyl of l to 4 carbon atoms
  • R is branched or straight chain alkyl of l to 3 carbon atoms and R; is selected from the group consisting of straight and branched chain alkyl of l to 3 carbon atoms, alkoxy of l to 3 carbon atoms and wherein R, R and R have the above definitions with a halogeno phosphate of the formula s LL/ORH wherein R and K; have the above definitions and Hal is chlorine or bromine in the presence of a hydrogen halide acceptor to form the corresponding compound of formula I.
  • the reaction is preferably effected in an organic solvent such as acetone, ethyl acetate or acetonitrile and Hal is chlorine and the acid.
  • acceptor may be potassium carbonate, triethylamine or pyridine, for example.
  • the starting material of formula II may be prepared by condensation of a 2-amino-pyridine or Z-aminopyrimidine, optionally substituted, with an ,optionally substituted aryl or alkyl malonate.
  • the compounds of formula II wherein R is chlorine or bromine can be prepared by reacting the corresponding compound of formula II wherein R is hydrogen with Nchloroor N- bromo-succinimide.
  • the compounds of formula II wherein R is alkoxycarbonyl may be prepared by reacting a trisalkoxycarbonylmethane with an optionally substituted aminopyridine or aminopyrimidine.
  • the novel pesticidal compositions of the invention are comprised of an effective amount of at least one compound of formula I and a carrier.
  • the compositions may also contain one or more other pesticidal agents and may be in the form of powders, granules, suspensions, emulsions or solutions containing the active ingredient in admixture, for example, with a vehicle and- /or cationic, anionic or non-ionic surface active agent to ensure a uniform dispersion of the substances in the composition.
  • the vehicle may be a liquid such as water, alcohol, hydrocarbons or other organic solvents, a mineral, vegetable or animal oil or a powder such as talc, clays, silicates or kieselguhr.
  • the liquid compositions preferably contain 5 to percent by weight of the active ingredient.
  • An example of an insecticidal composition of the invention is an emulsifiable concentrate consisting of 15 percent by weight of 2-( dimethoxythiophosphoryloxy pyrido [2, la]-pyrimidine-4-one:, 6.4 percent by weight of Atlox 4851 (oxyethylene triglyceride with a sulfonate having an acid No. of 1.5), 3.2 percent by weight of Atlox 4855 (oxyethylene triglyceride with a sulfonate having an acid No. of 3) and 75.4 percent by weight of xylene.
  • compositions are useful as insecticides, acari cides and nematocides. Tests have shown them to be useful to combat insects such as Aphis fabae, Prodenia lirura, Musca domestica, Drosopilila melanogaster, Blabera germanica, Simphilus granarius, Tribolium (0nfusum, Carpocapsa pomonella and C eraritis cupitata, to combat nematodes such as Mel oidogyn and to combat acarids such as Telranychus urlicae.
  • insects such as Aphis fabae, Prodenia lirura, Musca domestica, Drosopilila melanogaster, Blabera germanica, Simphilus granarius, Tribolium (0nfusum, Carpocapsa pomonella and C eraritis cupitata, to combat nematodes such as Mel oidogyn and to combat acarids such as Tel
  • the novel method of the invention for combatting acarids, insects or nematodes comprises contacting insects, nematodes and/or acarids with a lethal amount of at least one compound of formula I.
  • the oil was chromatographed over silica gel using as the eluant a l-l-l chloroform-acetonecyclohexane.
  • the eluant was evaporated to obtain 58 mg of 2-(diethoxythiophosphoryloxy )-pyrimido 1,2a]- pyrimidine-4-one in the form of a yellow oil.
  • EXAMPLE 8 2-( diethoxythiophosphoryloxy)-3-carbethoxy-pyrido l,2a]-pyrimidine-4-one
  • STEP A 2-hydroxy-3-carbethoxy-pyrido 1,2a]-pyrimidine-4-one
  • a mixture of 9.4 g of 2-amino-pyridine and 23.2 g of tricarbethoxymethane was heated at 200C until the distillation of ethanol ceased and after cooling, the residue was taken up in acetone.
  • the resulting crystals were recovered by vacuum filtration to obtain 15.5 g of 2hydroxy-3-carbethoxy-pyrido 1,2a1-pyrimidine- 4-0ne melting at 198C.
  • STEP B 2-(diethoxythiophosphoryloxy)-3-ch1oro-pyrido[ 1- l-pyrimidine-4-
  • the product was crystallized from 300 ml of an 8-2 isopropyl ether-benzene mixture to obtain 19 g of 2-(diethoxythiophosphoryloXy)-3- chloro-pyrido [1,2a]-pyrimidine-4one as white crystals melting at C.
  • STEP 1B 2-( diethoxythiophosphoryloxy )-7-nitro-pyrido 1,2a]-pyrimicline-4-one
  • a mixture of 21 g of the product of Step A and 12 g of potassium tert.-buty1ate in ml of methanol was stirred for 2 hours at room temperature and was then evaporated to dryness.
  • the crystals were taken up in ether, filtered and then suspended in 300 m1 of acetonitrile:
  • Table I shows that compound A has interesting insecticidal activity against Aphis fabae.
  • Table III shows that compound B has interesting insecticidal activity against Musca domestica.
  • insects were placed in Petri dishes connected with a tergal velum to a crystallizer of the same diameter into which is placed an acetone solution of the test product which can be evaporated before introduction of the insects. 25 adult insects less than 48 hours were used for each test and three tests were run for each concentration. The percentage of mortality was determined by comparison with untreated controls after 4 and then 24 hours.
  • Test IV shows that compound B has interesting insecticidal activity against Drosophila melanogaster.
  • Cockroaches were selected by the criteria of their length and received a p. of an acetone solution of compound B between the second and third pairs of feet and after treatment, the insects were held penumbral at 20C and the percent of mortality was determined 24 and 48 hours and 5 days after the treatment. The results are in Table V.
  • NEMATOCIDAL ACTIVITY The nematocidical activity of compound B was determined with dirt infested with Meloidogyne S.p.p. placed in plastic sacks with a volume of about 3 liters. Nematocidal treatment was considered efficacious at a depth of 30 cm, a volume of 3 liters of dirt correspond ing to a surface of 100 or 10 ha (l00"' X 30 cm 3,000 cc or 3 liters). Each volume of infested dirt received 100 ml of an aqueous suspension containing 0.250 g of compound B to 250 Kg/ha.
  • the controls received 100 ml of water and the plastic sacks containing the dirt were sealed immediately after treatment and then stirred in a manner to obtain a good distribution of the product. Two weeks after the treatment, the sacks were opened and the dirt was used to plant St. Pierre tomato plants in different pots. 2 months after the planting, the number of galls existing on the roots were counted and there existed in effect a relation be tween the population of Meloidogynes in each pot and the number of galls. The results are reported for compound B as compared to controls in Table lX.
  • Ovicide Test Bean leaves were infested with 10 female Tetranychus urticae per leaf and had a coating of glue about its perimeter. The females were left for 24 hours and then were removed from the leaves. The infested leaves were divided into 2 groups: (a) the first group was treated with a spray of 2.5 ml of an aqueous solution of compound B for each leaf at a concentration of 50 or 10 mg per liter while using 4 leaves for each concentration and (b) the second control group was untreated. The number of eggs living was determined 9 days after the treatment and the results expressed as percent mortality of the eggs are reported in Table X.
  • R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms.
  • a compound of claim 1 which is 2-(diethoxythiophosphoryloxy)-pyrido l ,2a]-pyrimidine-4-one.
  • a compound of claim 1 which is 2- (dimethoxythiophosphoryloxy)-8-methyl-pyrido l,2a]-pyrimidine4-one.
  • a compound of claim 1 which is 2- (diethoxythiophosphoryloxy )-3-methyl-pyrido 1 ,2a pyrimidine-4-one.
  • a compound of claim 1 which is 2- (diethoxythiophosphoryloxy )-3-carbethoxy-pyrido l,2a]-pyrimidine-4-one.
  • a compound of claim 1 which is 2- (diethoxythiophosphoryloxy)3-chloro-pyrido 1 ,2a]- pyrimidine-4-one.
  • a compound of claim 1 which (diethoxythiophosphoryloxy )-7-nitro-pyrid0 pyrimidine-4-one.

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  • 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)
US394078A 1972-09-11 1973-09-04 Pyrido(1,2a)pyrimidinone thiophosphates Expired - Lifetime US3904624A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/589,466 US4000267A (en) 1972-09-11 1975-06-23 Insecticidal and acaricidal compositions employing pyrido[1,2a]pyrimidinone thiophosphates

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FR7232088A FR2198697B1 (ru) 1972-09-11 1972-09-11

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

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4152427A (en) * 1977-01-29 1979-05-01 Bayer Aktiengesellschaft Combating pests with substituted pyrimidinone [(di)-thio]-phosphoric(phosphonic) acid esters and ester-amides
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
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
US5863920A (en) * 1991-04-08 1999-01-26 Duquesne University Of The Holy Ghost Furo-pyrimidine derivatives and methods of making and using these derivatives
US5877178A (en) * 1991-04-08 1999-03-02 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
US6114339A (en) * 1991-04-08 2000-09-05 Duquesne University Of The Holy Ghost Derivatives of pyrido [2,3-D] and [3,2-D] pyrimidine method of 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
US6962920B2 (en) 1992-09-23 2005-11-08 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60125077U (ja) * 1984-01-30 1985-08-23 織田　義男 釘打用支持具
JP2532677Y2 (ja) * 1991-03-13 1997-04-16 株式会社 日本バノック 固縛具
JP6250656B2 (ja) * 2012-06-19 2017-12-20 ダウ グローバル テクノロジーズ エルエルシー 水含有システムにおける抗微生物用複素環式化合物の使用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2245386A1 (de) * 1971-09-16 1973-03-22 Roussel Uclaf Heterocyclische organophosphorderivate, verfahren zu deren herstellung und diese verbindungen enthaltende insektizide zusammensetzungen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1239695B (de) * 1964-12-24 1967-05-03 Bayer Ag Verfahren zur Herstellung von Phosphor-, Phosphon-, Thionophosphor- oder Thiono-phosphonsaeureestern

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2245386A1 (de) * 1971-09-16 1973-03-22 Roussel Uclaf Heterocyclische organophosphorderivate, verfahren zu deren herstellung und diese verbindungen enthaltende insektizide zusammensetzungen
FR2152469A1 (ru) * 1971-09-16 1973-04-27 Roussel Uclaf

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4152427A (en) * 1977-01-29 1979-05-01 Bayer Aktiengesellschaft Combating pests with substituted pyrimidinone [(di)-thio]-phosphoric(phosphonic) acid esters and ester-amides
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
US5939420A (en) * 1991-04-08 1999-08-17 Duquesne University Of The Holy Ghost Pyrrolo 2,3d!derivatives
US6103727A (en) * 1991-04-08 2000-08-15 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US5736547A (en) * 1991-04-08 1998-04-07 Duquesne University Of The Holy Ghost Derivatives of pyrido 2,3-D! and 3,2-D! Pyrimidine and quinazoline and method of using these derivatives
US5863920A (en) * 1991-04-08 1999-01-26 Duquesne University Of The Holy Ghost Furo-pyrimidine derivatives and methods of making and using these derivatives
US5866580A (en) * 1991-04-08 1999-02-02 Duguesne University Of The Holy Ghost Quinazoline derivatives and methods of using the same
US5877178A (en) * 1991-04-08 1999-03-02 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these 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
US6077844A (en) * 1991-04-08 2000-06-20 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US6096750A (en) * 1991-04-08 2000-08-01 Duquesne University Of The Holy Ghost Furopyrimidines and methods of making and using the same 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
US6696455B1 (en) 1991-04-08 2004-02-24 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US6114339A (en) * 1991-04-08 2000-09-05 Duquesne University Of The Holy Ghost Derivatives of pyrido [2,3-D] and [3,2-D] pyrimidine method of using these derivatives
US6420370B1 (en) 1991-04-08 2002-07-16 Duquesne University Of The Holy Ghost Pyrimidine derivatives and method of making and using derivatives
US6518426B1 (en) 1991-04-08 2003-02-11 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and 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

Also Published As

Publication number Publication date
ES418627A1 (es) 1976-02-16
SU733504A3 (ru) 1980-05-05
ZA735709B (en) 1974-10-30
NL7312432A (ru) 1974-03-13
CH575430A5 (ru) 1976-05-14
IT1047946B (it) 1980-10-20
FR2198697B1 (ru) 1975-09-12
DE2345762A1 (de) 1974-03-21
HU168852B (ru) 1976-07-28
JPS4992096A (ru) 1974-09-03
DK138899C (ru) 1979-04-23
SU507246A3 (ru) 1976-03-15
TR18108A (tr) 1976-09-30
JPS5648481B2 (ru) 1981-11-16
IL43034A (en) 1976-05-31
YU240473A (en) 1981-08-31
BR7306999D0 (pt) 1974-06-27
DD109316A5 (ru) 1974-11-05
BE804654A (fr) 1974-03-11
OA04553A (fr) 1980-04-30
GB1408718A (en) 1975-10-01
DK138899B (da) 1978-11-13
FR2198697A1 (ru) 1974-04-05
IL43034A0 (en) 1973-11-28
GT198065690A (es) 1982-03-27
DE2345762B2 (de) 1977-04-21
YU36304B (en) 1982-06-18

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