DE2405733C2 - Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Pilzen - Google Patents
Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und PilzenInfo
- Publication number
- DE2405733C2 DE2405733C2 DE2405733A DE2405733A DE2405733C2 DE 2405733 C2 DE2405733 C2 DE 2405733C2 DE 2405733 A DE2405733 A DE 2405733A DE 2405733 A DE2405733 A DE 2405733A DE 2405733 C2 DE2405733 C2 DE 2405733C2
- Authority
- DE
- Germany
- Prior art keywords
- cjh
- preparation
- fungi
- mites
- acid derivatives
- 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
- 239000002253 acid Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 9
- 241000233866 Fungi Species 0.000 title description 6
- 238000000034 method Methods 0.000 title description 6
- 241000238876 Acari Species 0.000 title description 5
- 241000238631 Hexapoda Species 0.000 title description 4
- 150000003839 salts Chemical class 0.000 title description 4
- 239000000460 chlorine Substances 0.000 description 40
- 239000004480 active ingredient Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical class O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NWWZLDXOHWTTKD-UHFFFAOYSA-N 1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CN1C(=O)CC(=O)N(C)C1=S NWWZLDXOHWTTKD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 101100279441 Caenorhabditis elegans egg-5 gene Proteins 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101100408383 Mus musculus Piwil1 gene Proteins 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241001608568 Phaedon Species 0.000 description 1
- 241000308483 Phialophora cinerescens Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- -1 ligroin Chemical class 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07D239/66—Thiobarbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2405733A DE2405733C2 (de) | 1974-02-07 | 1974-02-07 | Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Pilzen |
| EG43/75A EG11930A (en) | 1974-02-07 | 1975-02-01 | Amidocarbonythiobarbituric acid derivatives process for their preparation and their use as insecticides and plant protection agents |
| BE153028A BE825150A (fr) | 1974-02-07 | 1975-02-04 | Nouveaux acides amidocarbonylthiobarbituriques et leurs sels, leur procede de preparation et leur application,comme insecticides,acaricides et fongicides |
| AU77862/75A AU486146B2 (en) | 1974-02-07 | 1975-02-04 | Pesticidal 2-amidocarbonyl-thiobarbituric acids agents |
| IL7546560A IL46560A0 (en) | 1974-02-07 | 1975-02-04 | Amidocarbonylthiobarbituric acid derivatives,their preparation and their use as insecticides and plant protection agents |
| LU71798A LU71798A1 (en, 2012) | 1974-02-07 | 1975-02-05 | |
| US05/547,421 US3961061A (en) | 1974-02-07 | 1975-02-05 | Pesticidal 2-amidocarbonylthiobarbituric acids |
| JP50014466A JPS6028824B2 (ja) | 1974-02-07 | 1975-02-05 | アミドカルボニルチオバルビツル酸誘導体の製造法 |
| RO7581350A RO72872A (ro) | 1974-02-07 | 1975-02-05 | Procedeu pentru prepararea derivatilor acidului aminocarbonil tiobarbituric |
| DD184020A DD118787A5 (en, 2012) | 1974-02-07 | 1975-02-05 | |
| CH137075A CH569721A5 (en, 2012) | 1974-02-07 | 1975-02-05 | |
| IT19966/75A IT1046799B (it) | 1974-02-07 | 1975-02-05 | Derivati dell acido amido carbonillio barbiturico e loro sali procedimento per la loro preparazione e loro impiego cme insetticidi acaricidi e funghicidi |
| SU7502102624A SU578826A3 (ru) | 1974-02-07 | 1975-02-05 | Способ борьбы с насекомыми, клещами и грибками |
| JP50014467A JPS6012322B2 (ja) | 1974-02-07 | 1975-02-05 | 作物保護剤 |
| BR763/75A BR7500763A (pt) | 1974-02-07 | 1975-02-06 | Processo para a preparacao de derivados de acido amidocarboniltiobarbiturico com os seus sais bem como composicoes inseticidas acaricidas e fungicidas a base destes |
| IE241/75A IE40586B1 (en) | 1974-02-07 | 1975-02-06 | Aminocarbonylthiobarbituric acid derivatives, process for their preparation and their use as insecticides, and plantprotection agents |
| ZA00750776A ZA75776B (en) | 1974-02-07 | 1975-02-06 | Amidocarbonylthiobarbituric acid derivatives, process for their preparation and their use as insecticides and plant protection agents |
| TR18425A TR18425A (tr) | 1974-02-07 | 1975-02-06 | Amido karboniltiobarbitrueik asit tuerevleri ve bunlarin tuzlari bunlarin hazirlanmasina mahsus usul ve bunlarin insektisid akarisid ve fungisid olarak kullanilmalari |
| DK41675A DK137126C (da) | 1974-02-07 | 1975-02-06 | Insecticidt,acaricidt og fungicidt virksomme aminocarbonylthiobarbitursyrederivater og deres salte til anvendelse ved plantebeskyttelse og andre tekniske formaal |
| NLAANVRAGE7501429,A NL180214C (nl) | 1974-02-07 | 1975-02-06 | Werkwijze voor het bereiden van op de 5-plaats gesubstitueerde thiobarbituurzuurderivaten alsmede werkwijze voor het bereiden van preparaten met een pesticide werking op basis van dergelijke thiobarbituurzuurderivaten. |
| GB508475A GB1454471A (en) | 1974-02-07 | 1975-02-06 | Aminocarbonyl-thiobarbituric acid derivatives process for their preparation and their use as insecticides and plant protection agents |
| PL1975177829A PL99856B1 (pl) | 1974-02-07 | 1975-02-06 | Srodek owadobojczy,roztoczobojczy i grzybobojczy |
| CA219,504A CA1034128A (en) | 1974-02-07 | 1975-02-06 | Amidocarbonylthiobarbituric acid derivatives, process for their preparation and their use as insecticides, and plant protection agents |
| HU75BA00003200A HU171226B (hu) | 1974-02-07 | 1975-02-07 | Insekticidnye, akaricidnye i fungicidnye kompozicii, i sposob poluchenija proizvodnykh amidokarbonil-tiobarbiturovojj kisloty i soli primenimykh aktivnymi agentami |
| FR7503892A FR2260578B1 (en, 2012) | 1974-02-07 | 1975-02-07 | |
| AT95275*#A AT334689B (de) | 1974-02-07 | 1975-02-07 | Insektizides, akarizides bzw. fungizides mittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2405733A DE2405733C2 (de) | 1974-02-07 | 1974-02-07 | Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Pilzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2405733A1 DE2405733A1 (de) | 1975-08-21 |
| DE2405733C2 true DE2405733C2 (de) | 1984-12-13 |
Family
ID=5906793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2405733A Expired DE2405733C2 (de) | 1974-02-07 | 1974-02-07 | Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Pilzen |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3961061A (en, 2012) |
| JP (2) | JPS6012322B2 (en, 2012) |
| AT (1) | AT334689B (en, 2012) |
| BE (1) | BE825150A (en, 2012) |
| BR (1) | BR7500763A (en, 2012) |
| CA (1) | CA1034128A (en, 2012) |
| CH (1) | CH569721A5 (en, 2012) |
| DD (1) | DD118787A5 (en, 2012) |
| DE (1) | DE2405733C2 (en, 2012) |
| DK (1) | DK137126C (en, 2012) |
| EG (1) | EG11930A (en, 2012) |
| FR (1) | FR2260578B1 (en, 2012) |
| GB (1) | GB1454471A (en, 2012) |
| HU (1) | HU171226B (en, 2012) |
| IE (1) | IE40586B1 (en, 2012) |
| IL (1) | IL46560A0 (en, 2012) |
| IT (1) | IT1046799B (en, 2012) |
| LU (1) | LU71798A1 (en, 2012) |
| NL (1) | NL180214C (en, 2012) |
| PL (1) | PL99856B1 (en, 2012) |
| RO (1) | RO72872A (en, 2012) |
| SU (1) | SU578826A3 (en, 2012) |
| TR (1) | TR18425A (en, 2012) |
| ZA (1) | ZA75776B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2601780B2 (de) * | 1976-01-20 | 1979-07-26 | Bayer Ag, 5090 Leverkusen | N-Phenyl-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE2719777A1 (de) * | 1976-05-06 | 1977-11-24 | Ciba Geigy Ag | Neue 5-phenylcarbamoyl-barbitursaeuren |
| PL103086B1 (pl) * | 1976-05-06 | 1979-05-31 | Ciba Geigy Ag | Srodek owadobojczy |
| DE2832698A1 (de) * | 1978-07-26 | 1980-02-07 | Bayer Ag | Substituierte 5-phenylcarbamoyl- barbitursaeuren, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| US4283444A (en) * | 1978-09-12 | 1981-08-11 | Ciba-Geigy Corporation | Method of protecting keratinous material from attack by insects that feed on keratin by treatment with 5-phenylcarbamoylbarbituric acid compounds |
| GB2145087B (en) * | 1983-08-19 | 1987-02-04 | Ciba Geigy Ag | Barbituric acid derivatives |
| IL73840A (en) * | 1983-12-19 | 1988-11-15 | Uniroyal Chem Co Inc | 2-thio-5-(thio)carbamoyl barbituric acid derivatives,their preparation and pharmaceutical compositions containing them |
| GB8431832D0 (en) * | 1983-12-19 | 1985-01-30 | Uniroyal Inc | 5-pyrimidinecarboxamides |
| EP0167491A3 (de) * | 1984-07-06 | 1986-12-30 | Ciba-Geigy Ag | Thiobarbitursäurederivate |
| PH24423A (en) * | 1985-02-15 | 1990-06-25 | Ciba Geigy Ag | 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics |
| US4636508A (en) * | 1985-04-22 | 1987-01-13 | Uniroyal Chemical Company, Inc. | 5-pyrimidinecarboxyamides and treatment of leukemia therewith |
| US4845217A (en) * | 1985-05-17 | 1989-07-04 | Uniroyal Chemical Ltd./Ltee | Purification of 5-pyrimidinecarboxamides |
| GB8531815D0 (en) * | 1985-12-24 | 1986-02-05 | Wellcome Found | Insecticidal compounds |
| US4920126A (en) * | 1988-05-10 | 1990-04-24 | Uniroyal Chemical Ltd/Uniroyal Chemical Ltee | Barbituric acid derivative and treatment of leukemia and tumors therewith |
| US20020192841A1 (en) * | 2001-04-27 | 2002-12-19 | Masayoshi Kojima | Measurement chip for biosensor |
| US20250185656A1 (en) * | 2022-03-09 | 2025-06-12 | Adeka Corporation | Piperidinone derivative or salt thereof, harmful organism control agent containing said compound, and method for using same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636080A (en) * | 1967-02-27 | 1972-01-18 | Hoffmann La Roche | Substituted phenylmalonic acid and phenylalkyl malonic acid esters |
| GB1339748A (en) * | 1970-07-02 | 1973-12-05 | Ici Ltd | Pyrimidine derivatives |
-
1974
- 1974-02-07 DE DE2405733A patent/DE2405733C2/de not_active Expired
-
1975
- 1975-02-01 EG EG43/75A patent/EG11930A/xx active
- 1975-02-04 BE BE153028A patent/BE825150A/xx not_active IP Right Cessation
- 1975-02-04 IL IL7546560A patent/IL46560A0/xx unknown
- 1975-02-05 RO RO7581350A patent/RO72872A/ro unknown
- 1975-02-05 SU SU7502102624A patent/SU578826A3/ru active
- 1975-02-05 CH CH137075A patent/CH569721A5/xx not_active IP Right Cessation
- 1975-02-05 JP JP50014467A patent/JPS6012322B2/ja not_active Expired
- 1975-02-05 JP JP50014466A patent/JPS6028824B2/ja not_active Expired
- 1975-02-05 DD DD184020A patent/DD118787A5/xx unknown
- 1975-02-05 IT IT19966/75A patent/IT1046799B/it active
- 1975-02-05 LU LU71798A patent/LU71798A1/xx unknown
- 1975-02-05 US US05/547,421 patent/US3961061A/en not_active Expired - Lifetime
- 1975-02-06 NL NLAANVRAGE7501429,A patent/NL180214C/xx not_active IP Right Cessation
- 1975-02-06 BR BR763/75A patent/BR7500763A/pt unknown
- 1975-02-06 ZA ZA00750776A patent/ZA75776B/xx unknown
- 1975-02-06 PL PL1975177829A patent/PL99856B1/pl unknown
- 1975-02-06 DK DK41675A patent/DK137126C/da not_active IP Right Cessation
- 1975-02-06 IE IE241/75A patent/IE40586B1/xx unknown
- 1975-02-06 CA CA219,504A patent/CA1034128A/en not_active Expired
- 1975-02-06 GB GB508475A patent/GB1454471A/en not_active Expired
- 1975-02-06 TR TR18425A patent/TR18425A/xx unknown
- 1975-02-07 HU HU75BA00003200A patent/HU171226B/hu unknown
- 1975-02-07 FR FR7503892A patent/FR2260578B1/fr not_active Expired
- 1975-02-07 AT AT95275*#A patent/AT334689B/de not_active IP Right Cessation
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