DE3143303A1 - Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide - Google Patents
Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizideInfo
- Publication number
- DE3143303A1 DE3143303A1 DE19813143303 DE3143303A DE3143303A1 DE 3143303 A1 DE3143303 A1 DE 3143303A1 DE 19813143303 DE19813143303 DE 19813143303 DE 3143303 A DE3143303 A DE 3143303A DE 3143303 A1 DE3143303 A1 DE 3143303A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- phenyl
- formula
- parts
- pyridazinone
- 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.)
- Withdrawn
Links
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000417 fungicide Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Chemical group 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- -1 cyclohexyl sulfonyl Chemical group 0.000 claims description 37
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 230000002538 fungal effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 239000004480 active ingredient Substances 0.000 description 29
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 229960000583 acetic acid Drugs 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
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- 238000010410 dusting Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- 240000004160 Capsicum annuum Species 0.000 description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
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- 239000012990 dithiocarbamate Substances 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002917 insecticide Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- PKDBSOOYVOEUQR-UHFFFAOYSA-N mucobromic acid Natural products OC1OC(=O)C(Br)=C1Br PKDBSOOYVOEUQR-UHFFFAOYSA-N 0.000 description 1
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- HZFSIJCQPSIJHB-UHFFFAOYSA-L zinc;n-methylcarbamodithioate Chemical compound [Zn+2].CNC([S-])=S.CNC([S-])=S HZFSIJCQPSIJHB-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/18—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813143303 DE3143303A1 (de) | 1981-10-31 | 1981-10-31 | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE8282109671T DE3266708D1 (en) | 1981-10-31 | 1982-10-20 | Pyridazinone derivatives, process for their preparation and their use as fungicides |
| EP82109671A EP0078450B1 (de) | 1981-10-31 | 1982-10-20 | Pyridazinon-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| AT82109671T ATE15896T1 (de) | 1981-10-31 | 1982-10-20 | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide. |
| IL67056A IL67056A (en) | 1981-10-31 | 1982-10-25 | Fungicidal compositions containing 5-halo-4-sulphinyl(sulphonyl)pyridazin-6-one derivatives,certain novel such compounds and their preparation |
| CA000414165A CA1192195A (en) | 1981-10-31 | 1982-10-26 | Pyridazinone derivatives, their preparation and their use as fungicides |
| JP57187663A JPS5885869A (ja) | 1981-10-31 | 1982-10-27 | ピリダジノン誘導体、該誘導体を含有する殺菌剤及び該誘導体による菌の防除方法 |
| DD82244345A DD204606A5 (de) | 1981-10-31 | 1982-10-28 | Fungizide mittel |
| HU823480A HU187795B (en) | 1981-10-31 | 1982-10-29 | Fungicides containing pyridazinone-derivatives and process for the production of the active substances |
| AU89887/82A AU551618B2 (en) | 1981-10-31 | 1982-10-29 | Pyridazinone derivatives |
| NZ202325A NZ202325A (en) | 1981-10-31 | 1982-10-29 | Pyridazinones and plant-protecting fungicides |
| CS827700A CS233739B2 (en) | 1981-10-31 | 1982-10-29 | Fungicide agent and processing of effective component |
| PL1982238801A PL130664B2 (en) | 1981-10-31 | 1982-10-29 | Fungicide and method of manufacture of novel derivative of pyridazinone used as an active substance |
| ZA827922A ZA827922B (en) | 1981-10-31 | 1982-10-29 | Pyridazinone derivatives, their preparation and their use as fungicides |
| US06/754,666 US4820704A (en) | 1981-10-31 | 1985-07-11 | Pyridazinone derivatives and their use as fungicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813143303 DE3143303A1 (de) | 1981-10-31 | 1981-10-31 | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3143303A1 true DE3143303A1 (de) | 1983-05-11 |
Family
ID=6145325
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813143303 Withdrawn DE3143303A1 (de) | 1981-10-31 | 1981-10-31 | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE8282109671T Expired DE3266708D1 (en) | 1981-10-31 | 1982-10-20 | Pyridazinone derivatives, process for their preparation and their use as fungicides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282109671T Expired DE3266708D1 (en) | 1981-10-31 | 1982-10-20 | Pyridazinone derivatives, process for their preparation and their use as fungicides |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4820704A (en, 2012) |
| EP (1) | EP0078450B1 (en, 2012) |
| JP (1) | JPS5885869A (en, 2012) |
| AT (1) | ATE15896T1 (en, 2012) |
| AU (1) | AU551618B2 (en, 2012) |
| CA (1) | CA1192195A (en, 2012) |
| CS (1) | CS233739B2 (en, 2012) |
| DD (1) | DD204606A5 (en, 2012) |
| DE (2) | DE3143303A1 (en, 2012) |
| HU (1) | HU187795B (en, 2012) |
| IL (1) | IL67056A (en, 2012) |
| NZ (1) | NZ202325A (en, 2012) |
| PL (1) | PL130664B2 (en, 2012) |
| ZA (1) | ZA827922B (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663324A (en) * | 1983-08-10 | 1987-05-05 | Basf Aktiengesellschaft | Pyridazinone derivatives, their preparation and their use as fungicides |
| US4837217A (en) * | 1985-04-19 | 1989-06-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
| US4874861A (en) * | 1984-11-29 | 1989-10-17 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
| US4877787A (en) * | 1983-06-23 | 1989-10-31 | Nissan Chemical Industries | Benzylthio pyridazinone derivatives, preparation thereof, and insecticidal acaricidal, fungicidal compositions |
| US4906627A (en) * | 1986-02-08 | 1990-03-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4945091A (en) * | 1987-07-30 | 1990-07-31 | Nissan Chemical Industries, Ltd. | 3(2H)-pyridazinone compounds derivatives and compositions for controlling and/or preventing insect pests intermediates for such compounds, and a process for their manufacture |
| DE3824211A1 (de) * | 1988-07-16 | 1990-01-18 | Basf Ag | 2-tert.-butyl-4-chlor-5-(4-tert.- butylbenzylthio)-3(2h)-pyridazinon zur bekaempfung von schnecken |
| DE3844227A1 (de) * | 1988-12-29 | 1990-07-05 | Basf Ag | 3(2h)-pyridazinonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| US5286725A (en) * | 1990-09-17 | 1994-02-15 | Ministero Dell'universita' E Della Ricerca Scientifica E Technologica | Pyridazinones endowed with acaricide and insecticide action |
| JPH0557344U (ja) * | 1991-12-26 | 1993-07-30 | テイケイ気化器株式会社 | 気化器の速度制限装置 |
| JPH0557343U (ja) * | 1991-12-26 | 1993-07-30 | テイケイ気化器株式会社 | 気化器 |
| US5670504A (en) * | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| KR20240166533A (ko) * | 2022-03-28 | 2024-11-26 | 니혼노야쿠가부시키가이샤 | 1-아릴테트라히드로피리다진-3,5-디온 유도체 또는 그의 염류 및 해당 화합물을 함유하는 살충제 그리고 그 사용 방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3063824A (en) * | 1960-01-29 | 1962-11-13 | Stauffer Chemical Co | Method of combatting weeds |
| BE627826A (en, 2012) * | 1960-09-09 | |||
| US3050440A (en) * | 1960-10-13 | 1962-08-21 | Velsicol Chemical Corp | New fungicidal compositions of matter |
| GB938890A (en) * | 1961-02-03 | 1963-10-09 | Boots Pure Drug Co Ltd | New fungicidal compositions and compounds |
| US4089964A (en) * | 1969-02-13 | 1978-05-16 | Kumiai Chemical Industry Co., Ltd. | Method of controlling fungal diseases in plants and compositions effective therefor |
-
1981
- 1981-10-31 DE DE19813143303 patent/DE3143303A1/de not_active Withdrawn
-
1982
- 1982-10-20 EP EP82109671A patent/EP0078450B1/de not_active Expired
- 1982-10-20 DE DE8282109671T patent/DE3266708D1/de not_active Expired
- 1982-10-20 AT AT82109671T patent/ATE15896T1/de active
- 1982-10-25 IL IL67056A patent/IL67056A/xx unknown
- 1982-10-26 CA CA000414165A patent/CA1192195A/en not_active Expired
- 1982-10-27 JP JP57187663A patent/JPS5885869A/ja active Granted
- 1982-10-28 DD DD82244345A patent/DD204606A5/de not_active IP Right Cessation
- 1982-10-29 NZ NZ202325A patent/NZ202325A/en unknown
- 1982-10-29 CS CS827700A patent/CS233739B2/cs unknown
- 1982-10-29 AU AU89887/82A patent/AU551618B2/en not_active Ceased
- 1982-10-29 ZA ZA827922A patent/ZA827922B/xx unknown
- 1982-10-29 HU HU823480A patent/HU187795B/hu not_active IP Right Cessation
- 1982-10-29 PL PL1982238801A patent/PL130664B2/xx unknown
-
1985
- 1985-07-11 US US06/754,666 patent/US4820704A/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4877787A (en) * | 1983-06-23 | 1989-10-31 | Nissan Chemical Industries | Benzylthio pyridazinone derivatives, preparation thereof, and insecticidal acaricidal, fungicidal compositions |
| US5026850A (en) * | 1983-06-23 | 1991-06-25 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, fungicidal compositions |
| US4663324A (en) * | 1983-08-10 | 1987-05-05 | Basf Aktiengesellschaft | Pyridazinone derivatives, their preparation and their use as fungicides |
| US4874861A (en) * | 1984-11-29 | 1989-10-17 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
| US4837217A (en) * | 1985-04-19 | 1989-06-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
| US4906627A (en) * | 1986-02-08 | 1990-03-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5885869A (ja) | 1983-05-23 |
| NZ202325A (en) | 1985-08-30 |
| EP0078450A2 (de) | 1983-05-11 |
| ZA827922B (en) | 1983-09-28 |
| CA1192195A (en) | 1985-08-20 |
| AU8988782A (en) | 1983-05-05 |
| IL67056A0 (en) | 1983-02-23 |
| DD204606A5 (de) | 1983-12-07 |
| PL130664B2 (en) | 1984-08-31 |
| HU187795B (en) | 1986-02-28 |
| ATE15896T1 (de) | 1985-10-15 |
| EP0078450B1 (de) | 1985-10-02 |
| JPH0480906B2 (en, 2012) | 1992-12-21 |
| US4820704A (en) | 1989-04-11 |
| CS233739B2 (en) | 1985-03-14 |
| AU551618B2 (en) | 1986-05-08 |
| EP0078450A3 (en) | 1983-06-22 |
| PL238801A2 (en) | 1983-07-04 |
| DE3266708D1 (en) | 1985-11-07 |
| IL67056A (en) | 1985-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |