DE2719777A1 - Neue 5-phenylcarbamoyl-barbitursaeuren - Google Patents
Neue 5-phenylcarbamoyl-barbitursaeurenInfo
- Publication number
- DE2719777A1 DE2719777A1 DE19772719777 DE2719777A DE2719777A1 DE 2719777 A1 DE2719777 A1 DE 2719777A1 DE 19772719777 DE19772719777 DE 19772719777 DE 2719777 A DE2719777 A DE 2719777A DE 2719777 A1 DE2719777 A1 DE 2719777A1
- Authority
- DE
- Germany
- Prior art keywords
- acid according
- methyl
- carbamoyl
- barbituric acid
- carbamoy1
- 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.)
- Granted
Links
- ACJWUHXBHCZMAF-UHFFFAOYSA-N 2,4,6-trioxo-5-phenyl-1,3-diazinane-5-carboxamide Chemical class C=1C=CC=CC=1C1(C(=O)N)C(=O)NC(=O)NC1=O ACJWUHXBHCZMAF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- -1 3-trifluoromethylphenyl- Chemical group 0.000 claims description 21
- 241000238631 Hexapoda Species 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 241000258916 Leptinotarsa decemlineata Species 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 241000254175 Anthonomus grandis Species 0.000 claims description 5
- 241000736227 Lucilia sericata Species 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 241000255925 Diptera Species 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- JWITUPUOSQIZMF-UHFFFAOYSA-N 1,3-diethyl-2,4,6-trioxo-5-[4-(trifluoromethyl)phenyl]-1,3-diazinane-5-carboxamide Chemical compound O=C1N(CC)C(=O)N(CC)C(=O)C1(C(N)=O)C1=CC=C(C(F)(F)F)C=C1 JWITUPUOSQIZMF-UHFFFAOYSA-N 0.000 claims 1
- RIOZXLMGZMUXMB-UHFFFAOYSA-N 1,3-dimethyl-2,4,6-trioxo-5-[3-(trifluoromethyl)phenyl]-1,3-diazinane-5-carboxamide Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=CC(C(F)(F)F)=C1 RIOZXLMGZMUXMB-UHFFFAOYSA-N 0.000 claims 1
- SBAMLXNTFGVOBJ-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(Cl)C=C1Cl SBAMLXNTFGVOBJ-UHFFFAOYSA-N 0.000 claims 1
- BVASGROKESFRKD-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-1-ethyl-3-methyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(CC)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(Cl)C=C1Cl BVASGROKESFRKD-UHFFFAOYSA-N 0.000 claims 1
- BKZUCQWGFMEILT-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-1-methyl-3-(2-methylpropyl)-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound ClC1=C(C=CC(=C1)Cl)C1(C(N(C(N(C1=O)C)=O)CC(C)C)=O)C(N)=O BKZUCQWGFMEILT-UHFFFAOYSA-N 0.000 claims 1
- OGYVCRQGPJIRLW-UHFFFAOYSA-N 5-(4-bromophenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical class O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(Br)C=C1 OGYVCRQGPJIRLW-UHFFFAOYSA-N 0.000 claims 1
- VBEWJDQJSFHQTA-UHFFFAOYSA-N 5-(4-bromophenyl)-1-ethyl-3-methyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound BrC1=CC=C(C=C1)C1(C(N(C(N(C1=O)C)=O)CC)=O)C(N)=O VBEWJDQJSFHQTA-UHFFFAOYSA-N 0.000 claims 1
- VMQDYYQQWZPQKB-UHFFFAOYSA-N 5-(4-chloro-2-methylphenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound ClC1=CC(=C(C=C1)C1(C(N(C(N(C1=O)C)=O)C)=O)C(N)=O)C VMQDYYQQWZPQKB-UHFFFAOYSA-N 0.000 claims 1
- DBRUAMAAQFNADQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(Cl)C=C1 DBRUAMAAQFNADQ-UHFFFAOYSA-N 0.000 claims 1
- MSTOQLUTVUMEMX-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-methyl-2,4,6-trioxo-3-propan-2-yl-1,3-diazinane-5-carboxamide Chemical compound ClC1=CC=C(C=C1)C1(C(N(C(N(C1=O)C)=O)C(C)C)=O)C(N)=O MSTOQLUTVUMEMX-UHFFFAOYSA-N 0.000 claims 1
- QIQKNTFENLJLHO-UHFFFAOYSA-N 5-(4-fluorophenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(F)C=C1 QIQKNTFENLJLHO-UHFFFAOYSA-N 0.000 claims 1
- QVYQQYGJKNEPLX-UHFFFAOYSA-N 5-(4-iodophenyl)-1,3-dimethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(C(N)=O)C1=CC=C(I)C=C1 QVYQQYGJKNEPLX-UHFFFAOYSA-N 0.000 claims 1
- NOYLJWYLPOXYGO-UHFFFAOYSA-N 5-[3,5-bis(trifluoromethyl)phenyl]-1,3-diethyl-2,4,6-trioxo-1,3-diazinane-5-carboxamide Chemical compound O=C1N(CC)C(=O)N(CC)C(=O)C1(C(N)=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NOYLJWYLPOXYGO-UHFFFAOYSA-N 0.000 claims 1
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- 150000002085 enols Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH568776A CH617067A5 (en) | 1976-05-06 | 1976-05-06 | Insecticide containing a 5-phenylcarbamoylbarbituric acid as active ingredient |
| CH1385076 | 1976-11-03 | ||
| CH1530176 | 1976-12-03 | ||
| CH398177 | 1977-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2719777A1 true DE2719777A1 (de) | 1977-11-24 |
| DE2719777C2 DE2719777C2 (enrdf_load_stackoverflow) | 1989-09-21 |
Family
ID=27428711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772719777 Granted DE2719777A1 (de) | 1976-05-06 | 1977-05-03 | Neue 5-phenylcarbamoyl-barbitursaeuren |
Country Status (12)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936457A1 (de) * | 1978-09-12 | 1980-03-20 | Ciba Geigy Ag | Verfahren zum schuetzen von keratinischen materialien vor dem befall durch keratinfressende insekten und neue 5-phenylcarbamoyl-barbitursaeureverbindungen |
| EP0191474A1 (de) * | 1985-02-15 | 1986-08-20 | Ciba-Geigy Ag | Barbitursäurederivate |
| EP0192180A1 (de) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)barbitursäure-derivate als Wirkstoffe für Anthelmintika |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2832698A1 (de) * | 1978-07-26 | 1980-02-07 | Bayer Ag | Substituierte 5-phenylcarbamoyl- barbitursaeuren, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| US4636508A (en) * | 1985-04-22 | 1987-01-13 | Uniroyal Chemical Company, Inc. | 5-pyrimidinecarboxyamides and treatment of leukemia therewith |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2405733A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Amidocarbonylthiobarbitursaeurederivate und deren salze, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und fungizide |
-
1977
- 1977-05-03 DE DE19772719777 patent/DE2719777A1/de active Granted
- 1977-05-03 NZ NZ183999A patent/NZ183999A/xx unknown
- 1977-05-04 FR FR7713509A patent/FR2350344A1/fr active Granted
- 1977-05-04 NL NL7704917A patent/NL7704917A/xx not_active Application Discontinuation
- 1977-05-04 CA CA277,691A patent/CA1074316A/en not_active Expired
- 1977-05-05 AT AT319077A patent/AT353553B/de not_active IP Right Cessation
- 1977-05-05 BE BE177291A patent/BE854287A/xx not_active IP Right Cessation
- 1977-05-05 AU AU24925/77A patent/AU508533B2/en not_active Expired
- 1977-05-05 IT IT23237/77A patent/IT1075534B/it active
- 1977-05-05 IL IL52019A patent/IL52019A/xx unknown
- 1977-05-05 GB GB18901/77A patent/GB1539493A/en not_active Expired
- 1977-05-06 JP JP5193477A patent/JPS52136181A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2405733A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Amidocarbonylthiobarbitursaeurederivate und deren salze, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und fungizide |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2936457A1 (de) * | 1978-09-12 | 1980-03-20 | Ciba Geigy Ag | Verfahren zum schuetzen von keratinischen materialien vor dem befall durch keratinfressende insekten und neue 5-phenylcarbamoyl-barbitursaeureverbindungen |
| EP0191474A1 (de) * | 1985-02-15 | 1986-08-20 | Ciba-Geigy Ag | Barbitursäurederivate |
| EP0192180A1 (de) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)barbitursäure-derivate als Wirkstoffe für Anthelmintika |
| US4762830A (en) * | 1985-02-15 | 1988-08-09 | Ciba-Geigy Corporation | 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2350344A1 (fr) | 1977-12-02 |
| DE2719777C2 (enrdf_load_stackoverflow) | 1989-09-21 |
| GB1539493A (en) | 1979-01-31 |
| IL52019A (en) | 1980-09-16 |
| NZ183999A (en) | 1978-09-20 |
| FR2350344B1 (enrdf_load_stackoverflow) | 1981-08-21 |
| JPS52136181A (en) | 1977-11-14 |
| AT353553B (de) | 1979-11-26 |
| IL52019A0 (en) | 1977-07-31 |
| ATA319077A (de) | 1979-04-15 |
| BE854287A (fr) | 1977-11-07 |
| AU508533B2 (en) | 1980-03-27 |
| NL7704917A (nl) | 1977-11-08 |
| CA1074316A (en) | 1980-03-25 |
| JPS6231712B2 (enrdf_load_stackoverflow) | 1987-07-09 |
| AU2492577A (en) | 1978-11-09 |
| IT1075534B (it) | 1985-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |