CS249139B2 - Insecticide,acaricide,nematocide and/or fungicide and method of its efficient component production - Google Patents
Insecticide,acaricide,nematocide and/or fungicide and method of its efficient component production Download PDFInfo
- Publication number
- CS249139B2 CS249139B2 CS844736A CS473684A CS249139B2 CS 249139 B2 CS249139 B2 CS 249139B2 CS 844736 A CS844736 A CS 844736A CS 473684 A CS473684 A CS 473684A CS 249139 B2 CS249139 B2 CS 249139B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- align
- group
- formula
- integer
- halogen
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 21
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 20
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000002917 insecticide Substances 0.000 title description 7
- 239000005645 nematicide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- 239000000417 fungicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 19
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 39
- -1 C1 -C6 alkyl Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 244000045947 parasite Species 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000003898 horticulture Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004969 haloethyl group Chemical group 0.000 claims 1
- GLGQMFICPMIOHO-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-sulfanylpyridazin-3-one Chemical compound CC(C)(C)N1N=CC(S)=C(Cl)C1=O GLGQMFICPMIOHO-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 190
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 163
- 238000012360 testing method Methods 0.000 description 69
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 201000010099 disease Diseases 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000013078 crystal Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 240000008067 Cucumis sativus Species 0.000 description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 241000238631 Hexapoda Species 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 13
- 241000239290 Araneae Species 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000004793 Polystyrene Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000011081 inoculation Methods 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000004495 emulsifiable concentrate Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241000819999 Nymphes Species 0.000 description 7
- 241000488589 Tetranychus kanzawai Species 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003905 agrochemical Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 241001143352 Meloidogyne Species 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 230000003071 parasitic effect Effects 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 230000001766 physiological effect Effects 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- 101100231507 Caenorhabditis elegans ceh-2 gene Proteins 0.000 description 4
- 235000009849 Cucumis sativus Nutrition 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000227653 Lycopersicon Species 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 241000358422 Nephotettix cincticeps Species 0.000 description 4
- 241000488581 Panonychus citri Species 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ANFVZRTXGLHTNI-UHFFFAOYSA-N 2-tert-butyl-4,5-dichloropyridazin-3-one Chemical compound CC(C)(C)N1N=CC(Cl)=C(Cl)C1=O ANFVZRTXGLHTNI-UHFFFAOYSA-N 0.000 description 3
- 241000256059 Culex pipiens Species 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241001299255 Henosepilachna Species 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000488585 Panonychus Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UIYKSYBJKIMANV-UHFFFAOYSA-N (4-tert-butylphenyl)methanethiol Chemical compound CC(C)(C)C1=CC=C(CS)C=C1 UIYKSYBJKIMANV-UHFFFAOYSA-N 0.000 description 2
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 2
- WAXIFMGAKWIFDQ-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CCl)C=C1 WAXIFMGAKWIFDQ-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000005944 Chlorpyrifos Substances 0.000 description 2
- 241001672694 Citrus reticulata Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- 241001480796 Haemaphysalis Species 0.000 description 2
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- 241000317981 Podosphaera fuliginea Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 229960005286 carbaryl Drugs 0.000 description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003874 central nervous system depressant Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 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 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000001418 larval effect Effects 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXXNHWIDDXSCBG-UHFFFAOYSA-N 1-(4-tert-butylphenyl)ethyl acetate Chemical compound CC(=O)OC(C)C1=CC=C(C(C)(C)C)C=C1 HXXNHWIDDXSCBG-UHFFFAOYSA-N 0.000 description 1
- RXANAHTWXCJFDF-UHFFFAOYSA-N 1-(bromomethyl)-4-[4-(trifluoromethyl)phenoxy]benzene Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(CBr)C=C1 RXANAHTWXCJFDF-UHFFFAOYSA-N 0.000 description 1
- QZNQSIHCDAGZIA-UHFFFAOYSA-N 1-(bromomethyl)-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(CBr)C=C1 QZNQSIHCDAGZIA-UHFFFAOYSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- DIBZQQBBZISGKH-UHFFFAOYSA-N 2-[(4-tert-butylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CSN1C(=O)C=CC=N1 DIBZQQBBZISGKH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AIMKITGMTPSIPK-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-[(2-methylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound CC1=CC=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 AIMKITGMTPSIPK-UHFFFAOYSA-N 0.000 description 1
- WPSIDNDGSXGJTI-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-[(4-cyclopropylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound O=C1N(C(C)(C)C)N=CC(SCC=2C=CC(=CC=2)C2CC2)=C1Cl WPSIDNDGSXGJTI-UHFFFAOYSA-N 0.000 description 1
- JULYUTQBTUIWFW-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-[(4-heptylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound C1=CC(CCCCCCC)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 JULYUTQBTUIWFW-UHFFFAOYSA-N 0.000 description 1
- VJJHNYCZBDUGCL-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-[(4-hexylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound C1=CC(CCCCCC)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 VJJHNYCZBDUGCL-UHFFFAOYSA-N 0.000 description 1
- XBPQLOGKPPCVCV-UHFFFAOYSA-N 2-tert-butyl-5-[1-(4-tert-butylphenyl)ethylsulfanyl]-4-chloropyridazin-3-one Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(C)SC=1C=NN(C(C)(C)C)C(=O)C=1Cl XBPQLOGKPPCVCV-UHFFFAOYSA-N 0.000 description 1
- KJEYWGXQUPGWLZ-UHFFFAOYSA-N 4,5-dibromo-2-tert-butylpyridazin-3-one Chemical compound CC(C)(C)N1N=CC(Br)=C(Br)C1=O KJEYWGXQUPGWLZ-UHFFFAOYSA-N 0.000 description 1
- GNNWQXXVYMDQMS-UHFFFAOYSA-N 4-bromo-2-tert-butyl-5-[(4-tert-butylphenyl)methylsulfanyl]pyridazin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Br)C(=O)N(C(C)(C)C)N=C1 GNNWQXXVYMDQMS-UHFFFAOYSA-N 0.000 description 1
- POGSRXABAVKYBB-UHFFFAOYSA-N 4-bromo-2-tert-butyl-5-sulfanylpyridazin-3-one Chemical compound CC(C)(C)N1N=CC(S)=C(Br)C1=O POGSRXABAVKYBB-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 241001480737 Amblyomma maculatum Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000537377 Fraxinus berlandieriana Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000179420 Haemaphysalis longicornis Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 241000359016 Nephotettix Species 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 241001480837 Rhipicephalus annulatus Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000003953 foreskin Anatomy 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229940115425 methylbenzyl acetate Drugs 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- PIIHPBHYDCOPKZ-UHFFFAOYSA-N n-fluoro-n-methylmethanamine Chemical compound CN(C)F PIIHPBHYDCOPKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001776 parthenogenetic effect Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58113409A JPS604173A (ja) | 1983-06-23 | 1983-06-23 | ピリダジノン誘導体,その製造法および殺虫・殺ダニ・殺菌剤 |
JP13887883A JPH06761B2 (ja) | 1983-07-29 | 1983-07-29 | ピリダジノン誘導体および殺虫・殺ダニ・殺線虫剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
CS473684A2 CS473684A2 (en) | 1985-12-16 |
CS249139B2 true CS249139B2 (en) | 1987-03-12 |
Family
ID=26452396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS844736A CS249139B2 (en) | 1983-06-23 | 1984-06-21 | Insecticide,acaricide,nematocide and/or fungicide and method of its efficient component production |
Country Status (22)
Country | Link |
---|---|
US (2) | US4877787A (xx) |
EP (2) | EP0239728A3 (xx) |
KR (1) | KR910004173B1 (xx) |
AR (1) | AR241472A1 (xx) |
AU (1) | AU572159B2 (xx) |
BG (1) | BG44025A3 (xx) |
BR (1) | BR8403090A (xx) |
CA (1) | CA1255676A (xx) |
CS (1) | CS249139B2 (xx) |
DD (1) | DD225039A5 (xx) |
DE (1) | DE3473594D1 (xx) |
EG (1) | EG17041A (xx) |
ES (1) | ES8506645A1 (xx) |
GR (1) | GR79933B (xx) |
HU (1) | HU194484B (xx) |
IL (1) | IL72204A (xx) |
PL (1) | PL148603B1 (xx) |
PT (1) | PT78781B (xx) |
RO (2) | RO92793B (xx) |
RU (1) | RU2054422C1 (xx) |
TR (1) | TR21892A (xx) |
YU (1) | YU45185B (xx) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GR79933B (xx) * | 1983-06-23 | 1984-10-31 | Nissan Chemical Ind Ltd | |
EP0183212B1 (en) * | 1984-11-29 | 1990-06-20 | 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 |
ZA87704B (en) * | 1986-02-08 | 1987-09-30 | Nissan Chemical Ind Ltd | Pyridazinone derivatives,preparation thereof,and insecticidal,acaricidal,nematicidal,fungicidal compositions |
JPS63112566A (ja) * | 1986-10-28 | 1988-05-17 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
DE3742266A1 (de) * | 1987-12-12 | 1989-06-22 | Basf Ag | 2-tert.-butyl-5-isoxazolylmethylthio-3(2h)-pyridazin-3-on-derivate |
EP0331529A3 (en) * | 1988-03-03 | 1991-11-21 | Ube Industries, Ltd. | Diphenyl ether derivatives, process for producing the same and insecticide and acaricide containing the same as active ingredient |
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 |
DE3824210A1 (de) * | 1988-07-16 | 1990-01-18 | Basf Ag | 3(2h)-pyridazinonderivate zur bekaempfung von schnecken |
US5004744A (en) * | 1988-12-13 | 1991-04-02 | Bayer Aktiengesellschaft | Pyridazinones as pesticides |
DE3844227A1 (de) * | 1988-12-29 | 1990-07-05 | Basf Ag | 3(2h)-pyridazinonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
IT1229684B (it) * | 1989-04-05 | 1991-09-06 | Mini Ricerca Scient Tecnolog | Piridazinoni ad attivita' insetticida ed acaricida |
JPH02279676A (ja) * | 1989-04-19 | 1990-11-15 | Otsuka Chem Co Ltd | ピリダジノン誘導体 |
US5286725A (en) * | 1990-09-17 | 1994-02-15 | Ministero Dell'universita' E Della Ricerca Scientifica E Technologica | Pyridazinones endowed with acaricide and insecticide action |
ES2104641T3 (es) * | 1990-10-17 | 1997-10-16 | Hoechst Schering Agrevo Gmbh | Derivados de pirimidina, procedimientos para su preparacion, agentes que los contienen y su utilizacion como fungicidas. |
EP0665223A1 (en) * | 1994-01-28 | 1995-08-02 | Takeda Chemical Industries, Ltd. | Antitumor agent, novel 3(2H)-pyridazinone derivatives and their preparation |
DE19615976A1 (de) * | 1996-04-22 | 1997-10-23 | Basf Ag | Mittel und Verfahren zur Bekämpfung von Schadpilzen |
AU6697300A (en) * | 1999-09-29 | 2001-04-30 | Basf Corporation | Pyridaben compounds for fungicidal uses |
CA2317778A1 (en) | 1999-09-29 | 2001-03-29 | Vivienne E. Harris | Synergistic insecticidal formulations of pyridaben and strobilurins |
DE10013914A1 (de) | 2000-03-21 | 2001-09-27 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
IL153440A0 (en) * | 2000-07-06 | 2003-07-06 | Sumitomo Chemical Co | Insecticides |
DE10055941A1 (de) | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
KR100834965B1 (ko) * | 2001-10-10 | 2008-06-03 | 에스케이케미칼주식회사 | 천연 살충 조성물 |
DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
EP2008517A1 (de) | 2007-06-29 | 2008-12-31 | Bayer CropScience AG | Akarizide Wirkstoffkombinationen |
DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
PE20121693A1 (es) | 2010-01-22 | 2012-12-01 | Bayer Ip Gmbh | Combinacion de espiromesifeno y abamectina como insecticidas |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
CN102726411B (zh) * | 2011-04-12 | 2013-12-11 | 深圳诺普信农化股份有限公司 | 一种杀螨剂及其应用 |
AU2013203000B9 (en) | 2012-08-10 | 2017-02-02 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
CN103125495A (zh) * | 2013-03-26 | 2013-06-05 | 海利尔药业集团股份有限公司 | 一种含有嘧螨醚与哒螨灵的杀螨组合物 |
CN103548834A (zh) * | 2013-10-22 | 2014-02-05 | 杭州市农业科学研究院 | 一种防治茶园螨类的复配农药及其使用方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2832780A (en) * | 1955-09-14 | 1958-04-29 | Warner Lambert Pharmaceutical | Hydrazides of pyridazonyl-substituted alkanoic acids |
NL288407A (xx) * | 1960-09-09 | |||
US3346577A (en) * | 1963-07-01 | 1967-10-10 | Sumitomo Chemical Co | Method for the preparation of 4-amino-3 (2h) pyridazinones |
US4177273A (en) * | 1977-02-14 | 1979-12-04 | Sandoz, Inc. | 6-(Substituted phenyl)-4,5-dihydro-pyridazin-3(2H)-ones |
DE3143303A1 (de) * | 1981-10-31 | 1983-05-11 | Basf Ag, 6700 Ludwigshafen | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
US4571397A (en) * | 1982-03-05 | 1986-02-18 | Nissan Chemical Industries | Pyridazinone derivatives, preparation thereof, and agricultural and horticultural fungicidal, insecticidal, acaricidal, nematicidal compositions containing said derivatives |
DE3321007A1 (de) * | 1983-06-10 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Substituierte 4,5-dimethoxypyridazone, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses als herbizide |
GR79933B (xx) * | 1983-06-23 | 1984-10-31 | Nissan Chemical Ind Ltd | |
DE3328770A1 (de) * | 1983-08-10 | 1985-02-28 | Basf Ag, 6700 Ludwigshafen | Pyridazinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
JPS61243078A (ja) * | 1985-04-19 | 1986-10-29 | Nissan Chem Ind Ltd | ピリダジノン誘導体,その製造法および殺虫・殺ダニ・殺線虫・殺菌剤 |
JPS61268672A (ja) * | 1985-05-22 | 1986-11-28 | Nissan Chem Ind Ltd | ピリダジノン誘導体、その製造法および殺虫・殺ダニ・殺菌剤 |
EP0183212B1 (en) * | 1984-11-29 | 1990-06-20 | Nissan Chemical Industries Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
JPS61130275A (ja) * | 1984-11-29 | 1986-06-18 | Nissan Chem Ind Ltd | ピリダジノン誘導体,その製造法および殺虫・殺ダニ・殺菌剤 |
JPH0641454B2 (ja) * | 1985-02-27 | 1994-06-01 | 日産化学工業株式会社 | ピリダジノン誘導体 |
US4837217A (en) * | 1985-04-19 | 1989-06-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
-
1984
- 1984-06-12 GR GR75092A patent/GR79933B/el unknown
- 1984-06-21 CS CS844736A patent/CS249139B2/cs unknown
- 1984-06-21 BG BG8465967A patent/BG44025A3/xx unknown
- 1984-06-21 YU YU1083/84A patent/YU45185B/xx unknown
- 1984-06-22 PT PT78781A patent/PT78781B/pt unknown
- 1984-06-22 RO RO120424A patent/RO92793B/ro unknown
- 1984-06-22 EP EP87100699A patent/EP0239728A3/en not_active Ceased
- 1984-06-22 DD DD84264438A patent/DD225039A5/de not_active IP Right Cessation
- 1984-06-22 HU HU842435A patent/HU194484B/hu unknown
- 1984-06-22 IL IL72204A patent/IL72204A/xx not_active IP Right Cessation
- 1984-06-22 DE DE8484107189T patent/DE3473594D1/de not_active Expired
- 1984-06-22 ES ES533636A patent/ES8506645A1/es not_active Expired
- 1984-06-22 CA CA000457326A patent/CA1255676A/en not_active Expired
- 1984-06-22 RO RO84114973A patent/RO88951A/ro unknown
- 1984-06-22 EP EP84107189A patent/EP0134439B1/en not_active Expired
- 1984-06-22 KR KR1019840003538A patent/KR910004173B1/ko not_active IP Right Cessation
- 1984-06-22 AR AR84296978A patent/AR241472A1/es active
- 1984-06-23 EG EG383/84A patent/EG17041A/xx active
- 1984-06-23 PL PL1984248375A patent/PL148603B1/pl unknown
- 1984-06-25 TR TR21892A patent/TR21892A/xx unknown
- 1984-06-25 AU AU29852/84A patent/AU572159B2/en not_active Expired
- 1984-06-25 BR BR8403090A patent/BR8403090A/pt not_active IP Right Cessation
-
1987
- 1987-03-17 US US07/027,191 patent/US4877787A/en not_active Expired - Lifetime
-
1989
- 1989-06-06 US US07/362,348 patent/US5026850A/en not_active Expired - Lifetime
-
1992
- 1992-02-20 RU SU925010935A patent/RU2054422C1/ru active
Also Published As
Publication number | Publication date |
---|---|
BR8403090A (pt) | 1985-05-28 |
BG44025A3 (en) | 1988-09-15 |
HUT34667A (en) | 1985-04-28 |
EP0134439A1 (en) | 1985-03-20 |
US5026850A (en) | 1991-06-25 |
EP0239728A2 (en) | 1987-10-07 |
KR850000399A (ko) | 1985-02-27 |
PL148603B1 (en) | 1989-11-30 |
RO88951A (ro) | 1986-04-30 |
GR79933B (xx) | 1984-10-31 |
US4877787A (en) | 1989-10-31 |
EP0239728A3 (en) | 1988-01-20 |
AU2985284A (en) | 1985-01-03 |
ES533636A0 (es) | 1985-08-01 |
IL72204A0 (en) | 1984-10-31 |
EP0134439B1 (en) | 1988-08-24 |
YU45185B (en) | 1992-05-28 |
DE3473594D1 (en) | 1988-09-29 |
RO92793A (ro) | 1987-11-30 |
PT78781A (en) | 1984-07-01 |
EG17041A (en) | 1991-08-30 |
RO92793B (ro) | 1987-12-01 |
PL248375A1 (en) | 1985-06-18 |
KR910004173B1 (ko) | 1991-06-24 |
DD225039A5 (de) | 1985-07-24 |
CS473684A2 (en) | 1985-12-16 |
TR21892A (tr) | 1985-10-07 |
HU194484B (en) | 1988-02-29 |
RU2054422C1 (ru) | 1996-02-20 |
AR241472A1 (es) | 1992-07-31 |
PT78781B (en) | 1986-06-26 |
YU108384A (en) | 1986-12-31 |
ES8506645A1 (es) | 1985-08-01 |
IL72204A (en) | 1987-12-31 |
AU572159B2 (en) | 1988-05-05 |
CA1255676A (en) | 1989-06-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CS249139B2 (en) | Insecticide,acaricide,nematocide and/or fungicide and method of its efficient component production | |
DE69104071T2 (de) | Uracilderivate und Pestizide, die diese als wirksame Stoffe enthalten. | |
EP0199281B1 (en) | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions | |
DK166208B (da) | Insekticide pyrazolinderivater og fremgangsmaade til fremstilling deraf, middel indeholdende derivaterne samt derivaternes anvendelse til bekaempelse af insekter og spindemider | |
EP0183212B1 (en) | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions | |
KR900006852B1 (ko) | 피리다지논 유도체 | |
JP2751309B2 (ja) | ピラゾール類およびこれを有効成分とする殺虫、殺ダニ、殺菌剤 | |
JPH0564140B2 (xx) | ||
JPS63112566A (ja) | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 | |
IE47663B1 (en) | Phenyl isothiocyanate derivatives | |
JPH0472830B2 (xx) | ||
JPH0670069B2 (ja) | チアジアビシクロノナン誘導体、その製造方法及び除草剤 | |
US4421761A (en) | Thiophene derivatives | |
KR970011302B1 (ko) | 제초성 퀴놀리닐옥사디아졸 유도체 | |
JPS6117570A (ja) | ピリダジノン誘導体、その製造法および殺虫・殺ダニ・殺菌剤 | |
KR19980702235A (ko) | 이속사졸 유도체 | |
JPS63159372A (ja) | ピリダジノン化合物および殺虫、殺ダニ、殺線虫剤 | |
US4039635A (en) | Soil fungicidal phosphorothioate | |
CN109553615B (zh) | 一种嘧啶盐类化合物及其用途 | |
JPS63159374A (ja) | ピリダジノン誘導体および殺虫、殺ダニ、殺線虫剤 | |
US5525580A (en) | Substituted benzoyl cyclic enone, process for preparation, and herbicide | |
JPS63201174A (ja) | ピリダジノン誘導体、その製造法および殺虫・殺ダニ・殺線虫・殺菌剤 | |
KR940002710B1 (ko) | 치환된 이소옥사졸계 피레스로이드 화합물 | |
SI8411083A8 (sl) | Postopek za pripravo derivatov 3(2h)-piridazinona | |
JPH0434538B2 (xx) |