CA1080226A - 6-oxo-pyrimidinyl(thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricides - Google Patents
6-oxo-pyrimidinyl(thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricidesInfo
- Publication number
- CA1080226A CA1080226A CA281,807A CA281807A CA1080226A CA 1080226 A CA1080226 A CA 1080226A CA 281807 A CA281807 A CA 281807A CA 1080226 A CA1080226 A CA 1080226A
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- methyl
- propyl
- butyl
- hydroxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 6-oxo-pyrimidinyl(thiono) Chemical class 0.000 title claims description 99
- 239000002253 acid Substances 0.000 title claims description 41
- 150000002148 esters Chemical class 0.000 title claims description 24
- 150000003573 thiols Chemical class 0.000 title claims description 15
- 230000000895 acaricidal effect Effects 0.000 title abstract description 8
- 239000000642 acaricide Substances 0.000 title abstract description 3
- 239000002917 insecticide Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 239000000203 mixture Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 241000244206 Nematoda Species 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 241000238421 Arthropoda Species 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762630054 DE2630054A1 (de) | 1976-07-03 | 1976-07-03 | 6-oxo-pyrimidinyl(thiono)(thiol)- phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080226A true CA1080226A (en) | 1980-06-24 |
Family
ID=5982170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,807A Expired CA1080226A (en) | 1976-07-03 | 1977-06-30 | 6-oxo-pyrimidinyl(thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricides |
Country Status (28)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130344A1 (de) * | 1981-07-31 | 1983-02-17 | Bayer Ag, 5090 Leverkusen | Oxo-chinazolin-(thiono)-phosphor(phosphon)- saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| 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 |
| DE3439363A1 (de) * | 1984-10-27 | 1986-04-30 | Bayer Ag, 5090 Leverkusen | Phosphorsaeureester |
| DE3605002A1 (de) * | 1986-02-18 | 1987-08-20 | Bayer Ag | Phosphorsaeureester |
| DE3704689A1 (de) * | 1987-02-14 | 1988-08-25 | Bayer Ag | Thionophosphonsaeureester |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE383635B (sv) * | 1971-03-04 | 1976-03-22 | Sandoz Ag | Insekticida och nematocida pyrimidinylfosforsyraestrar |
| US4045561A (en) * | 1973-03-23 | 1977-08-30 | Sandoz Ltd. | Pesticidal pyrimidinyl phosphorus esters |
| DE2523324A1 (de) * | 1975-05-27 | 1976-12-09 | Bayer Ag | Pyrimidin(4,6)diyl-bis-(thiono) (thiol)phosphor-(phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
-
1976
- 1976-07-03 DE DE19762630054 patent/DE2630054A1/de not_active Withdrawn
-
1977
- 1977-06-15 US US05/806,887 patent/US4152426A/en not_active Expired - Lifetime
- 1977-06-28 BG BG036746A patent/BG28069A3/xx unknown
- 1977-06-28 PT PT66731A patent/PT66731B/pt unknown
- 1977-06-28 CH CH795577A patent/CH627346A5/de not_active IP Right Cessation
- 1977-06-28 BG BG037553A patent/BG28422A3/bg unknown
- 1977-06-30 CS CS774353A patent/CS192487B2/cs unknown
- 1977-06-30 CA CA281,807A patent/CA1080226A/en not_active Expired
- 1977-06-30 IL IL7752420A patent/IL52420A/xx unknown
- 1977-06-30 NL NL7707289A patent/NL7707289A/xx not_active Application Discontinuation
- 1977-06-30 CS CS78445A patent/CS192498B2/cs unknown
- 1977-06-30 PH PH19939A patent/PH13898A/en unknown
- 1977-06-30 NZ NZ184524A patent/NZ184524A/xx unknown
- 1977-06-30 AR AR268257A patent/AR216474A1/es active
- 1977-06-30 GB GB27423/77A patent/GB1536643A/en not_active Expired
- 1977-06-30 SE SE7707604A patent/SE7707604L/xx unknown
- 1977-07-01 FR FR7720358A patent/FR2356663A1/fr active Granted
- 1977-07-01 AU AU26674/77A patent/AU508005B2/en not_active Expired
- 1977-07-01 ES ES460330A patent/ES460330A1/es not_active Expired
- 1977-07-01 JP JP7796077A patent/JPS535177A/ja active Pending
- 1977-07-01 AT AT472377A patent/AT356967B/de not_active IP Right Cessation
- 1977-07-01 DD DD7700199845A patent/DD131451A5/xx unknown
- 1977-07-01 BR BR7704324A patent/BR7704324A/pt unknown
- 1977-07-01 BE BE178998A patent/BE856371A/xx unknown
- 1977-07-01 ZA ZA00773986A patent/ZA773986B/xx unknown
- 1977-07-01 DK DK295277AA patent/DK141485B/da unknown
- 1977-07-02 PL PL1977199318A patent/PL102267B1/pl unknown
- 1977-07-02 RO RO7790906A patent/RO70727A/ro unknown
- 1977-07-03 EG EG392/77A patent/EG12866A/xx active
- 1977-07-04 TR TR19339A patent/TR19339A/xx unknown
-
1978
- 1978-05-29 ES ES470284A patent/ES470284A1/es not_active Expired
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