CA1125753A - Pyridazine derivatives and their use as agricultural fungicides - Google Patents
Pyridazine derivatives and their use as agricultural fungicidesInfo
- Publication number
- CA1125753A CA1125753A CA350,128A CA350128A CA1125753A CA 1125753 A CA1125753 A CA 1125753A CA 350128 A CA350128 A CA 350128A CA 1125753 A CA1125753 A CA 1125753A
- Authority
- CA
- Canada
- Prior art keywords
- group
- atom
- atoms
- phenyl
- dichloro
- 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
- 239000000417 fungicide Substances 0.000 title abstract description 23
- 150000004892 pyridazines Chemical class 0.000 title abstract description 5
- -1 N-substituted carbamoyloxy, carbamoylthio, thiocarbamoyl-oxy Chemical group 0.000 claims abstract description 49
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 149
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- ZGJMBHQAWVLWRN-UHFFFAOYSA-N butyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCCCC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 ZGJMBHQAWVLWRN-UHFFFAOYSA-N 0.000 claims description 5
- 244000053095 fungal pathogen Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- ZTCCXLJAHREOAV-UHFFFAOYSA-N [6-(3-bromophenyl)pyridazin-3-yl] morpholine-4-carboxylate Chemical compound BrC1=CC=CC(C=2N=NC(OC(=O)N3CCOCC3)=CC=2)=C1 ZTCCXLJAHREOAV-UHFFFAOYSA-N 0.000 claims description 3
- SFUKLUKIFPPXDZ-UHFFFAOYSA-N methyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 SFUKLUKIFPPXDZ-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- LRUBHXBHIDBKOV-UHFFFAOYSA-N [6-(3,5-dichloro-4-methylphenyl)pyridazin-3-yl] morpholine-4-carboxylate Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C(N=N1)=CC=C1OC(=O)N1CCOCC1 LRUBHXBHIDBKOV-UHFFFAOYSA-N 0.000 claims description 2
- BTOCHYCVYKTBLB-UHFFFAOYSA-N ethyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 BTOCHYCVYKTBLB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 229940060038 chlorine Drugs 0.000 claims 4
- 235000017168 chlorine Nutrition 0.000 claims 4
- HFYRNGCBWSQUCQ-UHFFFAOYSA-N benzyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(C(=O)OCC=2C=CC=CC=2)C(=O)C=C1 HFYRNGCBWSQUCQ-UHFFFAOYSA-N 0.000 claims 2
- VEVIXLHRQQVXEU-UHFFFAOYSA-N butyl 3-(3-bromophenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCCCC)N=C1C1=CC=CC(Br)=C1 VEVIXLHRQQVXEU-UHFFFAOYSA-N 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 abstract description 22
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 abstract description 16
- YQQSRZSUGBETRS-UHFFFAOYSA-N 1h-pyridazine-6-thione Chemical compound SC1=CC=CN=N1 YQQSRZSUGBETRS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000004009 herbicide Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 230000003902 lesion Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 241001617088 Thanatephorus sasakii Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 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 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
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- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- QWFIEKREUYUENM-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-propanethioylpyridazin-3-one Chemical compound C1=CC(=O)N(C(=S)CC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 QWFIEKREUYUENM-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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- 235000009852 Cucurbita pepo Nutrition 0.000 description 2
- 240000001980 Cucurbita pepo Species 0.000 description 2
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- 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
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 235000002597 Solanum melongena Nutrition 0.000 description 2
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- CDCLQDAODSNARQ-UHFFFAOYSA-N [6-(3,5-dichloro-4-methoxyphenyl)pyridazin-3-yl] morpholine-2-carboxylate Chemical compound ClC=1C=C(C=C(C=1OC)Cl)C1=CC=C(N=N1)OC(=O)C1CNCCO1 CDCLQDAODSNARQ-UHFFFAOYSA-N 0.000 description 2
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- 235000013339 cereals Nutrition 0.000 description 2
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- 238000004440 column chromatography Methods 0.000 description 2
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- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- UVBGBOYCUYAZLE-UHFFFAOYSA-N ethyl 3-(3,5-dichloro-4-methoxyphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCC)N=C1C1=CC(Cl)=C(OC)C(Cl)=C1 UVBGBOYCUYAZLE-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FMHOUTOUDUGWGC-UHFFFAOYSA-N hexyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCCCCCC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 FMHOUTOUDUGWGC-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- QDESFMLRHRZCSV-UHFFFAOYSA-M potassium;n-(hydroxymethyl)-n-methylcarbamodithioate Chemical compound [K+].OCN(C)C([S-])=S QDESFMLRHRZCSV-UHFFFAOYSA-M 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- WTQGLKIWEZOEMM-UHFFFAOYSA-N propan-2-yl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OC(C)C)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 WTQGLKIWEZOEMM-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- SNZPKGZOQOSGIC-UHFFFAOYSA-N propyl 3-(3,5-dichloro-4-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OCCC)N=C1C1=CC(Cl)=C(C)C(Cl)=C1 SNZPKGZOQOSGIC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- ZIGCWMHFDQRVMQ-UHFFFAOYSA-N s-[6-(3,5-dichloro-4-methylphenyl)pyridazin-3-yl] morpholine-4-carbothioate Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C(N=N1)=CC=C1SC(=O)N1CCOCC1 ZIGCWMHFDQRVMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
- AZXQLMRILCCVDW-UHFFFAOYSA-M sodium;5-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(C(C)C)=CC=CC2=C1S([O-])(=O)=O AZXQLMRILCCVDW-UHFFFAOYSA-M 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- 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
- C07D237/14—Oxygen atoms
-
- 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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4820979A JPS55139363A (en) | 1979-04-19 | 1979-04-19 | Pyridazine derivative, and agricultural and horticultural germicide containing pyridazine derivative as effective component |
| JP54-48209 | 1979-04-19 | ||
| JP54-48210 | 1979-04-19 | ||
| JP4821079A JPS55139364A (en) | 1979-04-19 | 1979-04-19 | Pyridazone derivative, and agricultural and horticultural germicide containing said derivative as effective component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125753A true CA1125753A (en) | 1982-06-15 |
Family
ID=26388443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA350,128A Expired CA1125753A (en) | 1979-04-19 | 1980-04-18 | Pyridazine derivatives and their use as agricultural fungicides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4279908A (Direct) |
| BR (1) | BR8002397A (Direct) |
| CA (1) | CA1125753A (Direct) |
| DE (1) | DE3014991A1 (Direct) |
| ES (1) | ES8104246A1 (Direct) |
| FR (2) | FR2454440A1 (Direct) |
| GB (1) | GB2047702B (Direct) |
| IT (1) | IT1128423B (Direct) |
| NL (1) | NL8002312A (Direct) |
| PH (1) | PH16653A (Direct) |
| SU (1) | SU984408A3 (Direct) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5826802A (ja) * | 1981-08-10 | 1983-02-17 | Sankyo Co Ltd | 農園芸用殺菌剤 |
| ATE54401T1 (de) * | 1985-06-14 | 1990-07-15 | Lilly Co Eli | Fungizide pyridazine. |
| AT397598B (de) * | 1990-04-05 | 1994-05-25 | Agrolinz Agrarchemikalien | Herbizides mittel |
| DE69122865T2 (de) * | 1990-05-15 | 1997-03-27 | Du Pont | Arthropodizide tetrahydropyridazine |
| CN1038249C (zh) * | 1991-08-28 | 1998-05-06 | 罗姆和哈斯公司 | 含有二氢哒嗪酮及其相关化合物的杀菌组合物 |
| KR100494058B1 (ko) * | 2001-05-24 | 2005-06-13 | 윤용진 | 신규한 1-아실(혹은 아로일) 피리다진-6-온 유도체, 그의제조방법 및 아실화 시약으로서의 용도 |
| EP1429604A4 (en) * | 2001-09-27 | 2005-03-30 | Monsanto Technology Llc | FUNGICIDE COMPOSITIONS AND ITS APPLICATION IN AGRICULTURE |
| RU2416609C2 (ru) * | 2005-12-07 | 2011-04-20 | Сумитомо Кемикал Компани, Лимитед | Соединение пиридазина и его применение |
| WO2008121877A2 (en) * | 2007-04-02 | 2008-10-09 | Institute For Oneworld Health | Cftr inhibitor compounds and uses thereof |
| WO2009131957A2 (en) * | 2008-04-21 | 2009-10-29 | Institute For Oneworld Health | Compounds, compositions and methods comprising oxadiazole derivatives |
| US20090270398A1 (en) * | 2008-04-21 | 2009-10-29 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Pyridazine Derivatives |
| WO2009131958A2 (en) * | 2008-04-21 | 2009-10-29 | Institute For Oneworld Health | Compounds, compositions and methods comprising triazine derivatives |
| US8236838B2 (en) * | 2008-04-21 | 2012-08-07 | Institute For Oneworld Health | Compounds, compositions and methods comprising isoxazole derivatives |
| US20110237528A1 (en) * | 2008-09-19 | 2011-09-29 | Institute For Oneworld Health | Compositions and methods comprising imidazole and triazole derivatives |
| US8511216B2 (en) * | 2009-03-30 | 2013-08-20 | Kanzaki Kokyukoki Mfg. Co., Ltd. | Hydraulic actuator unit |
| US8343976B2 (en) * | 2009-04-20 | 2013-01-01 | Institute For Oneworld Health | Compounds, compositions and methods comprising pyrazole derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2624730A (en) * | 1950-08-16 | 1953-01-06 | Sterling Drug Inc | 6-haloaryl-3-pyridazones |
| ES355900A1 (es) * | 1968-06-27 | 1969-12-16 | Inst De Investigaciones Terape | Procedimiento para la obtencion de compuestos de la serie de la piridazona. |
| US3862943A (en) * | 1971-09-08 | 1975-01-28 | Sandoz Ag | 2-Hydroxyalkyl-4,5-dihydropyridazin-3(2H)-one derivatives |
| US4052395A (en) * | 1975-09-11 | 1977-10-04 | Sankyo Company Limited | Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones |
-
1980
- 1980-04-07 US US06/137,779 patent/US4279908A/en not_active Expired - Lifetime
- 1980-04-15 GB GB8012333A patent/GB2047702B/en not_active Expired
- 1980-04-17 PH PH23912A patent/PH16653A/en unknown
- 1980-04-18 ES ES490722A patent/ES8104246A1/es not_active Expired
- 1980-04-18 DE DE19803014991 patent/DE3014991A1/de not_active Withdrawn
- 1980-04-18 IT IT67620/80A patent/IT1128423B/it active
- 1980-04-18 CA CA350,128A patent/CA1125753A/en not_active Expired
- 1980-04-18 SU SU802910349A patent/SU984408A3/ru active
- 1980-04-18 BR BR8002397A patent/BR8002397A/pt unknown
- 1980-04-21 FR FR8008889A patent/FR2454440A1/fr active Granted
- 1980-04-21 NL NL8002312A patent/NL8002312A/nl not_active Application Discontinuation
- 1980-09-19 FR FR8020170A patent/FR2460936A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2047702B (en) | 1983-08-03 |
| FR2454440B1 (Direct) | 1983-06-24 |
| FR2454440A1 (fr) | 1980-11-14 |
| IT8067620A0 (it) | 1980-04-18 |
| GB2047702A (en) | 1980-12-03 |
| US4279908A (en) | 1981-07-21 |
| ES490722A0 (es) | 1981-04-01 |
| FR2460936A1 (fr) | 1981-01-30 |
| NL8002312A (nl) | 1980-10-21 |
| DE3014991A1 (de) | 1980-10-30 |
| SU984408A3 (ru) | 1982-12-23 |
| BR8002397A (pt) | 1980-12-02 |
| ES8104246A1 (es) | 1981-04-01 |
| PH16653A (en) | 1983-12-06 |
| FR2460936B1 (Direct) | 1983-04-22 |
| IT1128423B (it) | 1986-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |