ZA200006976B - Substituted (4-brompyrazole-3-yl)benzazoles. - Google Patents
Substituted (4-brompyrazole-3-yl)benzazoles. Download PDFInfo
- Publication number
- ZA200006976B ZA200006976B ZA200006976A ZA200006976A ZA200006976B ZA 200006976 B ZA200006976 B ZA 200006976B ZA 200006976 A ZA200006976 A ZA 200006976A ZA 200006976 A ZA200006976 A ZA 200006976A ZA 200006976 B ZA200006976 B ZA 200006976B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- butyl
- formula
- carbonyl
- ethyl
- Prior art date
Links
- MIFWQUSMRKXDDR-UHFFFAOYSA-N 2-(4-bromo-1H-pyrazol-5-yl)-1H-indole Chemical class BrC1=CNN=C1C1=CC2=CC=CC=C2N1 MIFWQUSMRKXDDR-UHFFFAOYSA-N 0.000 title claims description 15
- -1 cyano, nitro, amino, hydroxyl Chemical group 0.000 claims description 438
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000005499 phosphonyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000035613 defoliation Effects 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000002837 defoliant Substances 0.000 claims description 7
- 239000002274 desiccant Substances 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000004094 surface-active agent Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- VGQYGJXBIRIZQJ-UHFFFAOYSA-N 4-azido-5-phenyl-1h-pyrazole Chemical compound [N-]=[N+]=NC1=CNN=C1C1=CC=CC=C1 VGQYGJXBIRIZQJ-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- YLYPTGYHGCWJGN-UHFFFAOYSA-N 5-phenyl-1h-pyrazol-4-amine Chemical compound C1=NNC(C=2C=CC=CC=2)=C1N YLYPTGYHGCWJGN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100224562 Mus musculus Drc7 gene Proteins 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000012954 diazonium Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 46
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
- 239000000460 chlorine Substances 0.000 description 31
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 1
- 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 description 1
- 125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 125000004707 1-methylethylthio group Chemical group CC(C)S* 0.000 description 1
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- CDYUXJBPCIBFNK-UHFFFAOYSA-N [O]C(=O)CC(F)(F)F Chemical group [O]C(=O)CC(F)(F)F CDYUXJBPCIBFNK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004788 dichlorofluoromethoxy group Chemical group ClC(O*)(F)Cl 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19819060 | 1998-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006976B true ZA200006976B (en) | 2002-05-23 |
Family
ID=7866105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006976A ZA200006976B (en) | 1998-04-29 | 2000-11-28 | Substituted (4-brompyrazole-3-yl)benzazoles. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6482774B1 (bg) |
| EP (1) | EP1076660B1 (bg) |
| JP (1) | JP2002513023A (bg) |
| KR (1) | KR20010034834A (bg) |
| CN (1) | CN1186342C (bg) |
| AR (1) | AR015048A1 (bg) |
| AT (1) | ATE219774T1 (bg) |
| AU (1) | AU758553B2 (bg) |
| BG (1) | BG64595B1 (bg) |
| BR (1) | BR9910061B1 (bg) |
| CA (1) | CA2329873A1 (bg) |
| DE (1) | DE59901862D1 (bg) |
| DK (1) | DK1076660T3 (bg) |
| EA (1) | EA003590B1 (bg) |
| ES (1) | ES2179652T3 (bg) |
| HU (1) | HUP0101623A3 (bg) |
| IL (1) | IL139092A0 (bg) |
| NZ (1) | NZ508356A (bg) |
| PL (1) | PL343795A1 (bg) |
| PT (1) | PT1076660E (bg) |
| SK (1) | SK15922000A3 (bg) |
| TW (1) | TW474915B (bg) |
| UA (1) | UA67776C2 (bg) |
| WO (1) | WO1999055702A1 (bg) |
| ZA (1) | ZA200006976B (bg) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001068644A1 (de) | 2000-03-16 | 2001-09-20 | Basf Aktiengesellschaft | Verfahren zur herstellung von 7-(pyrazol-3-yl)benzoxazolen |
| TW200305368A (en) * | 2001-12-19 | 2003-11-01 | Basf Ag | Herbicidal mixtures based on 7-pyrazolylbenzoxazoles |
| DE10235206A1 (de) * | 2002-08-01 | 2004-02-19 | Basf Ag | Verfahren zur Herstellung von (S)-3-Methylmino-1-(thien-2-yl)propan-1-ol |
| CN101279972B (zh) * | 2008-05-12 | 2011-02-02 | 大连理工大学 | 苯并噁唑类除草剂及其制备方法 |
| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5281571A (en) | 1990-10-18 | 1994-01-25 | Monsanto Company | Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles |
| GB9422708D0 (en) * | 1994-11-10 | 1995-01-04 | Zeneca Ltd | Herbicides |
| GB9422667D0 (en) | 1994-11-10 | 1995-01-04 | Zeneca Ltd | Herbicides |
| UA53679C2 (uk) * | 1996-12-16 | 2003-02-17 | Басф Акцієнгезелльшафт | Заміщені піразол-3-ілбензазоли, спосіб їх одержання (варіанти), гербіцидний засіб та спосіб його одержання, засіб для десикації і/або дефоліації рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин та спосіб десикації і/або дефоліації рослин |
| EP0964005A1 (en) * | 1998-06-10 | 1999-12-15 | Teijin Limited | Process for producing hydrogenated alpha-olefin-dicyclopentadiene copolymer, method for molding the same and optical material |
-
1999
- 1999-04-22 NZ NZ508356A patent/NZ508356A/xx unknown
- 1999-04-22 WO PCT/EP1999/002699 patent/WO1999055702A1/de not_active Application Discontinuation
- 1999-04-22 HU HU0101623A patent/HUP0101623A3/hu unknown
- 1999-04-22 US US09/673,996 patent/US6482774B1/en not_active Expired - Fee Related
- 1999-04-22 ES ES99920734T patent/ES2179652T3/es not_active Expired - Lifetime
- 1999-04-22 CN CNB998064572A patent/CN1186342C/zh not_active Expired - Fee Related
- 1999-04-22 AT AT99920734T patent/ATE219774T1/de not_active IP Right Cessation
- 1999-04-22 DK DK99920734T patent/DK1076660T3/da active
- 1999-04-22 IL IL13909299A patent/IL139092A0/xx not_active IP Right Cessation
- 1999-04-22 PL PL99343795A patent/PL343795A1/xx unknown
- 1999-04-22 UA UA2000116787A patent/UA67776C2/uk unknown
- 1999-04-22 PT PT99920734T patent/PT1076660E/pt unknown
- 1999-04-22 KR KR1020007012032A patent/KR20010034834A/ko not_active Application Discontinuation
- 1999-04-22 JP JP2000545862A patent/JP2002513023A/ja active Pending
- 1999-04-22 DE DE59901862T patent/DE59901862D1/de not_active Expired - Lifetime
- 1999-04-22 EA EA200001090A patent/EA003590B1/ru not_active IP Right Cessation
- 1999-04-22 EP EP99920734A patent/EP1076660B1/de not_active Expired - Lifetime
- 1999-04-22 CA CA002329873A patent/CA2329873A1/en not_active Abandoned
- 1999-04-22 AU AU38202/99A patent/AU758553B2/en not_active Ceased
- 1999-04-22 BR BRPI9910061-4A patent/BR9910061B1/pt not_active IP Right Cessation
- 1999-04-22 SK SK1592-2000A patent/SK15922000A3/sk unknown
- 1999-04-29 AR ARP990102000A patent/AR015048A1/es unknown
- 1999-04-29 TW TW088106951A patent/TW474915B/zh not_active IP Right Cessation
-
2000
- 2000-11-07 BG BG104925A patent/BG64595B1/bg unknown
- 2000-11-28 ZA ZA200006976A patent/ZA200006976B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1076660A1 (de) | 2001-02-21 |
| BR9910061A (pt) | 2000-12-26 |
| JP2002513023A (ja) | 2002-05-08 |
| ES2179652T3 (es) | 2003-01-16 |
| CA2329873A1 (en) | 1999-11-04 |
| PT1076660E (pt) | 2002-11-29 |
| BG64595B1 (bg) | 2005-08-31 |
| HUP0101623A3 (en) | 2002-03-28 |
| EP1076660B1 (de) | 2002-06-26 |
| UA67776C2 (uk) | 2004-07-15 |
| TW474915B (en) | 2002-02-01 |
| EA200001090A1 (ru) | 2001-04-23 |
| AR015048A1 (es) | 2001-04-11 |
| BR9910061B1 (pt) | 2009-08-11 |
| CN1302298A (zh) | 2001-07-04 |
| CN1186342C (zh) | 2005-01-26 |
| HUP0101623A2 (hu) | 2001-08-28 |
| IL139092A0 (en) | 2001-11-25 |
| DE59901862D1 (de) | 2002-08-01 |
| AU3820299A (en) | 1999-11-16 |
| DK1076660T3 (da) | 2002-07-22 |
| NZ508356A (en) | 2003-04-29 |
| US6482774B1 (en) | 2002-11-19 |
| AU758553B2 (en) | 2003-03-27 |
| EA003590B1 (ru) | 2003-06-26 |
| BG104925A (bg) | 2001-08-31 |
| SK15922000A3 (sk) | 2001-05-10 |
| WO1999055702A1 (de) | 1999-11-04 |
| PL343795A1 (en) | 2001-09-10 |
| ATE219774T1 (de) | 2002-07-15 |
| KR20010034834A (ko) | 2001-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7381687B2 (en) | 3-heteroaryl substituted 5-methyloxymethyl isoxazolines used as herbicides | |
| US20020025910A1 (en) | 3-heterocycly1 - substituted benzoyl derivatives | |
| ZA200006976B (en) | Substituted (4-brompyrazole-3-yl)benzazoles. | |
| US5958837A (en) | Substituted 2-phenylpyridines | |
| EP1047693A1 (de) | Herbizide 3-(benzazol-4-yl)pyrimidindion-derivate | |
| EP0944623B1 (de) | Substituierte pyrazol-3-ylbenzazole | |
| EP0802903A1 (de) | Substituierte 2-phenylpyridine als herbizide | |
| US6175007B1 (en) | Substituted aromatic phoshonic acid derivatives | |
| US6277790B1 (en) | Substituted herbicide tetrazolinonecarboxylic acid amides | |
| US6197973B1 (en) | Substituted 3-phenylpyrazoles | |
| US6100218A (en) | Substituted 2-phenylpyridines | |
| WO1999006394A1 (de) | Substituierte 2-(benzaryl)pyridine | |
| MXPA99005530A (en) | Substituted pyrazole-3-yl benzazoles | |
| ZA200105476B (en) | 3-(heterocyclyl)-benzoylpyrazole-derivatives. | |
| CZ20003987A3 (cs) | Substituované (4-brompyrazol-3yl)benzazoly | |
| WO2001087863A1 (de) | 3-arylisothiazole und ihre verwendung als herbizide | |
| MXPA00005040A (en) | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives | |
| EP1218350A1 (de) | 1-aryl-1,3-dihydro-imidazol-2-(thi)on derivate, deren herstellung und deren verwendung als herbizide oder zur desikkation/defoliation von pflanzen |