DE2339012A1 - Imidazochinoxaline als fungizide - Google Patents
Imidazochinoxaline als fungizideInfo
- Publication number
- DE2339012A1 DE2339012A1 DE2339012A DE2339012A DE2339012A1 DE 2339012 A1 DE2339012 A1 DE 2339012A1 DE 2339012 A DE2339012 A DE 2339012A DE 2339012 A DE2339012 A DE 2339012A DE 2339012 A1 DE2339012 A1 DE 2339012A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- imidazo
- ethyl
- quinoxaline
- chloro
- 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.)
- Pending
Links
- 239000000417 fungicide Substances 0.000 title claims description 7
- YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical compound N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- -1 ethoxycarbonylmethyl Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 5
- 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 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical class 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- GLURLAOFZMNBIQ-UHFFFAOYSA-N 6-chloro-2-ethyl-3h-imidazo[4,5-b]quinoxaline Chemical compound ClC1=CC=C2N=C(NC(CC)=N3)C3=NC2=C1 GLURLAOFZMNBIQ-UHFFFAOYSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000221785 Erysiphales Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 240000008067 Cucumis sativus Species 0.000 description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- FCTIZUUFUMDWEH-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC=N3)C3=NC2=C1 FCTIZUUFUMDWEH-UHFFFAOYSA-N 0.000 description 3
- PDGNZSMHXXKYAJ-UHFFFAOYSA-N 2-ethyl-1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC(CC)=N3)C3=NC2=C1 PDGNZSMHXXKYAJ-UHFFFAOYSA-N 0.000 description 3
- RQWVBQOUWJUMRS-UHFFFAOYSA-N 6-chloroquinoxaline-2,3-diamine Chemical compound C1=C(Cl)C=C2N=C(N)C(N)=NC2=C1 RQWVBQOUWJUMRS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RCCAJEUVMYNEFU-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)pentan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)CCCC)C(CC)=NC3=NC2=C1 RCCAJEUVMYNEFU-UHFFFAOYSA-N 0.000 description 2
- QRZBGBHHGQSEAW-UHFFFAOYSA-N 6-chloro-2-ethyl-4,9-dioxido-3H-imidazo[4,5-b]quinoxaline-4,9-diium Chemical compound ClC1=CC=C2[N+]([O-])=C(NC(CC)=N3)C3=[N+]([O-])C2=C1 QRZBGBHHGQSEAW-UHFFFAOYSA-N 0.000 description 2
- JJJRXRYQULGOTB-UHFFFAOYSA-N 6-chloro-2-methyl-3h-imidazo[4,5-b]quinoxaline Chemical compound ClC1=CC=C2N=C(NC(C)=N3)C3=NC2=C1 JJJRXRYQULGOTB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical group 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- SAEMKKTVBSCOFX-UHFFFAOYSA-N quinoxalin-1-ium;chloride Chemical compound Cl.N1=CC=NC2=CC=CC=C21 SAEMKKTVBSCOFX-UHFFFAOYSA-N 0.000 description 2
- LUDZVVVPVCUUBP-UHFFFAOYSA-N quinoxaline-2,3-diamine Chemical compound C1=CC=C2N=C(N)C(N)=NC2=C1 LUDZVVVPVCUUBP-UHFFFAOYSA-N 0.000 description 2
- 150000003252 quinoxalines Chemical class 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- XNQWJCZESZXTGA-UHFFFAOYSA-N (6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)-(2-fluorophenyl)methanone Chemical compound CCC1=NC2=NC3=CC(Cl)=CC=C3N=C2N1C(=O)C1=CC=CC=C1F XNQWJCZESZXTGA-UHFFFAOYSA-N 0.000 description 1
- LCVOCDOSGJHZFH-UHFFFAOYSA-N 1,1,2,2-tetrachloroethyl thiohypochlorite Chemical compound ClSC(Cl)(Cl)C(Cl)Cl LCVOCDOSGJHZFH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BOMPNTVEUWSFLI-UHFFFAOYSA-N 1-(2-butylimidazo[4,5-b]quinoxalin-3-yl)ethanone Chemical compound C1=CC=C2N=C(N(C(CCCC)=N3)C(C)=O)C3=NC2=C1 BOMPNTVEUWSFLI-UHFFFAOYSA-N 0.000 description 1
- WSDJWWPBZYWUBI-UHFFFAOYSA-N 1-(6-chloro-2-ethyl-4-oxido-9-oxoimidazo[4,5-b]quinoxalin-9-ium-1-yl)hexan-1-one Chemical compound ClC1=CC=C2[N+]([O-])=C3N(C(=O)CCCCC)C(CC)=NC3=[N+]([O-])C2=C1 WSDJWWPBZYWUBI-UHFFFAOYSA-N 0.000 description 1
- QEGOTFUEPYDYLM-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)-2-methylbutan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)C(C)CC)C(CC)=NC3=NC2=C1 QEGOTFUEPYDYLM-UHFFFAOYSA-N 0.000 description 1
- MZGLKPGQRRFLJT-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)-3-methylbut-2-en-1-one Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)C(=O)C=C(C)C)C3=NC2=C1 MZGLKPGQRRFLJT-UHFFFAOYSA-N 0.000 description 1
- FBKFKSIPQQFASA-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)decan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)CCCCCCCCC)C(CC)=NC3=NC2=C1 FBKFKSIPQQFASA-UHFFFAOYSA-N 0.000 description 1
- RUGGQFTYJLHRTB-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)hexan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)CCCCC)C(CC)=NC3=NC2=C1 RUGGQFTYJLHRTB-UHFFFAOYSA-N 0.000 description 1
- SCGPSHIYMBSHJT-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)nonan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)CCCCCCCC)C(CC)=NC3=NC2=C1 SCGPSHIYMBSHJT-UHFFFAOYSA-N 0.000 description 1
- QLDDOBPXFHUPEC-UHFFFAOYSA-N 1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)octan-1-one Chemical compound ClC1=CC=C2N=C3N(C(=O)CCCCCCC)C(CC)=NC3=NC2=C1 QLDDOBPXFHUPEC-UHFFFAOYSA-N 0.000 description 1
- VKMYERONEMZQPD-UHFFFAOYSA-N 2-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)acetic acid Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)CC(O)=O)C3=NC2=C1 VKMYERONEMZQPD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- ZAEDWRLGLPNQPQ-UHFFFAOYSA-N 2-methyl-1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC(C)=N3)C3=NC2=C1 ZAEDWRLGLPNQPQ-UHFFFAOYSA-N 0.000 description 1
- ZLVYTWOMKAXMHB-UHFFFAOYSA-N 2-propyl-1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC(CCC)=N3)C3=NC2=C1 ZLVYTWOMKAXMHB-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- VFQYSPNSMMMHNC-UHFFFAOYSA-N 3-methylimidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C3N(C)C=NC3=NC2=C1 VFQYSPNSMMMHNC-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- OJMSERXVMXKNBD-UHFFFAOYSA-N 6-bromo-2-ethyl-3h-imidazo[4,5-b]quinoxaline Chemical compound BrC1=CC=C2N=C(NC(CC)=N3)C3=NC2=C1 OJMSERXVMXKNBD-UHFFFAOYSA-N 0.000 description 1
- NLMMUTVMNOEDEE-UHFFFAOYSA-N 6-chloro-1,2-diethylimidazo[4,5-b]quinoxaline Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)CC)C3=NC2=C1 NLMMUTVMNOEDEE-UHFFFAOYSA-N 0.000 description 1
- IZGSTDDCBHYOPV-UHFFFAOYSA-N 6-chloro-2-cyclopropyl-3h-imidazo[4,5-b]quinoxaline Chemical compound N=1C2=NC3=CC(Cl)=CC=C3N=C2NC=1C1CC1 IZGSTDDCBHYOPV-UHFFFAOYSA-N 0.000 description 1
- HDJXZLNXYFHKPZ-UHFFFAOYSA-N 6-chloro-2-ethyl-1-(1,1,2,2-tetrachloroethylsulfanyl)imidazo[4,5-b]quinoxaline Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)SC(Cl)(Cl)C(Cl)Cl)C3=NC2=C1 HDJXZLNXYFHKPZ-UHFFFAOYSA-N 0.000 description 1
- TXAIXDKNUNVKPZ-UHFFFAOYSA-N 6-chloro-2-ethyl-1-methylimidazo[4,5-b]quinoxaline Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)C)C3=NC2=C1 TXAIXDKNUNVKPZ-UHFFFAOYSA-N 0.000 description 1
- FIYKSPFSMHPPNK-UHFFFAOYSA-N 6-chloro-2-ethyl-1-prop-2-ynylimidazo[4,5-b]quinoxaline;hydrochloride Chemical compound Cl.ClC1=CC=C2N=C(N(C(CC)=N3)CC#C)C3=NC2=C1 FIYKSPFSMHPPNK-UHFFFAOYSA-N 0.000 description 1
- SYCANHMRPHNURZ-UHFFFAOYSA-N 6-chloro-2-ethyl-n-methylimidazo[4,5-b]quinoxaline-1-carboxamide Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)C(=O)NC)C3=NC2=C1 SYCANHMRPHNURZ-UHFFFAOYSA-N 0.000 description 1
- OCFNBEPTHKXPGL-UHFFFAOYSA-N 6-chloro-2-ethyl-n-phenylimidazo[4,5-b]quinoxaline-1-carboxamide Chemical compound CCC1=NC2=NC3=CC(Cl)=CC=C3N=C2N1C(=O)NC1=CC=CC=C1 OCFNBEPTHKXPGL-UHFFFAOYSA-N 0.000 description 1
- XJAGHSWVTWHCFK-UHFFFAOYSA-N 6-fluoroquinoxaline-2,3-diamine Chemical compound C1=C(F)C=C2N=C(N)C(N)=NC2=C1 XJAGHSWVTWHCFK-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- OTUSNLYWMRAMQJ-UHFFFAOYSA-N methyl 6-chloro-2-ethylimidazo[4,5-b]quinoxaline-1-carboxylate Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)C(=O)OC)C3=NC2=C1 OTUSNLYWMRAMQJ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- RJOGLVWHIOTFGF-UHFFFAOYSA-N n,2-dimethylimidazo[4,5-b]quinoxaline-3-carboxamide Chemical compound C1=CC=C2N=C3N(C(=O)NC)C(C)=NC3=NC2=C1 RJOGLVWHIOTFGF-UHFFFAOYSA-N 0.000 description 1
- GUTALTICIZXUBM-UHFFFAOYSA-N n-(1,2,2,2-tetrachloroethyl)formamide Chemical compound ClC(Cl)(Cl)C(Cl)NC=O GUTALTICIZXUBM-UHFFFAOYSA-N 0.000 description 1
- XLJHDMMTSGBZLN-UHFFFAOYSA-N n-(3-aminoquinoxalin-2-yl)acetamide Chemical compound C1=CC=C2N=C(N)C(NC(=O)C)=NC2=C1 XLJHDMMTSGBZLN-UHFFFAOYSA-N 0.000 description 1
- KUBBFQOVCJRENS-UHFFFAOYSA-N n-[2,2,2-trichloro-1-(6-chloro-2-ethylimidazo[4,5-b]quinoxalin-1-yl)ethyl]formamide Chemical compound ClC1=CC=C2N=C(N(C(CC)=N3)C(NC=O)C(Cl)(Cl)Cl)C3=NC2=C1 KUBBFQOVCJRENS-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- SKLIKROKBBLQNU-UHFFFAOYSA-N n-butyl-6-chloro-2-ethylimidazo[4,5-b]quinoxaline-1-carboxamide Chemical compound ClC1=CC=C2N=C3N(C(=O)NCCCC)C(CC)=NC3=NC2=C1 SKLIKROKBBLQNU-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HEBPLCPSDSDYRG-UHFFFAOYSA-N quinoxaline;sodium Chemical compound [Na].N1=CC=NC2=CC=CC=C21 HEBPLCPSDSDYRG-UHFFFAOYSA-N 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/08—Systemic pesticides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27760472A | 1972-08-01 | 1972-08-01 | |
| US369740A US3919423A (en) | 1972-08-01 | 1973-06-13 | Imidazoquinoxaline fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2339012A1 true DE2339012A1 (de) | 1974-02-14 |
Family
ID=26958588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2339012A Pending DE2339012A1 (de) | 1972-08-01 | 1973-08-01 | Imidazochinoxaline als fungizide |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0681755B2 (ja) * | 1988-04-11 | 1994-10-19 | 富士写真フイルム株式会社 | イミダゾキノキサリニウム塩化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3705174A (en) * | 1970-02-27 | 1972-12-05 | Merck & Co Inc | Polyhaloalkyl benzimidazoles |
-
1973
- 1973-06-13 US US369740A patent/US3919423A/en not_active Expired - Lifetime
- 1973-07-30 ES ES417393A patent/ES417393A1/es not_active Expired
- 1973-07-30 JP JP48085033A patent/JPS4975726A/ja active Pending
- 1973-07-30 AU AU58663/73A patent/AU5866373A/en not_active Expired
- 1973-07-30 CH CH1108873A patent/CH585012A5/xx not_active IP Right Cessation
- 1973-07-31 IT IT27345/73A patent/IT995104B/it active
- 1973-07-31 HU HUDU207A patent/HU168197B/hu unknown
- 1973-07-31 IL IL42856A patent/IL42856A/en unknown
- 1973-07-31 FR FR7328047A patent/FR2194371B1/fr not_active Expired
- 1973-07-31 DK DK421473AA patent/DK133578B/da unknown
- 1973-07-31 DD DD170089A patent/DD108194A5/xx unknown
- 1973-07-31 CA CA177,829A patent/CA1010451A/en not_active Expired
- 1973-08-01 GB GB3500175A patent/GB1430278A/en not_active Expired
- 1973-08-01 NL NL7310658A patent/NL7310658A/xx unknown
- 1973-08-01 PH PH14874A patent/PH10508A/en unknown
- 1973-08-01 GB GB3649973A patent/GB1430277A/en not_active Expired
- 1973-08-01 MX MX145289A patent/MX147028A/es unknown
- 1973-08-01 DE DE2339012A patent/DE2339012A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1430277A (en) | 1976-03-31 |
| ES417393A1 (es) | 1976-07-16 |
| FR2194371A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-01 |
| HU168197B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-28 |
| IL42856A0 (en) | 1973-10-25 |
| US3919423A (en) | 1975-11-11 |
| IT995104B (it) | 1975-11-10 |
| IL42856A (en) | 1976-03-31 |
| JPS4975726A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-22 |
| PH10508A (en) | 1977-05-24 |
| NL7310658A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-05 |
| AU5866373A (en) | 1975-01-30 |
| FR2194371B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-13 |
| CH585012A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-28 |
| CA1010451A (en) | 1977-05-17 |
| DK133578C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-01 |
| MX147028A (es) | 1982-09-23 |
| DK133578B (da) | 1976-06-14 |
| GB1430278A (en) | 1976-03-31 |
| DD108194A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-12 |
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