UA79245C2 - Pyrazolyl-substituted heterocycles and intermediary compounds, agents for controlling pests and a method for obtaining these agents - Google Patents

Info

Publication number

UA79245C2

UA79245C2 UA20040503843A UA20040503843A UA79245C2 UA 79245 C2 UA79245 C2 UA 79245C2 UA 20040503843 A UA20040503843 A UA 20040503843A UA 20040503843 A UA20040503843 A UA 20040503843A UA 79245 C2 UA79245 C2 UA 79245C2

Authority

UA

Ukraine

Prior art keywords

alkyl

necessary

methyl

formula

compounds

Prior art date

2001-10-22

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 127
• 238000000034 method Methods 0.000 title claims description 88
• 241000607479 Yersinia pestis Species 0.000 title claims description 19
• 125000000623 heterocyclic group Chemical class 0.000 title abstract description 3
• 239000004009 herbicide Substances 0.000 claims abstract description 14
• 230000003641 microbiacidal effect Effects 0.000 claims abstract description 5
• 229940124561 microbicide Drugs 0.000 claims abstract description 5
• -1 trifluoromethyl phenyl Chemical group 0.000 claims description 188
• 239000013543 active substance Substances 0.000 claims description 125
• 229910052760 oxygen Inorganic materials 0.000 claims description 64
• 239000000460 chlorine Substances 0.000 claims description 55
• 229910052801 chlorine Inorganic materials 0.000 claims description 55
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 239000003085 diluting agent Substances 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 41
• 229910052796 boron Inorganic materials 0.000 claims description 39
• 239000001301 oxygen Substances 0.000 claims description 39
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 36
• 229910052794 bromium Inorganic materials 0.000 claims description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 150000002431 hydrogen Chemical class 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 239000003795 chemical substances by application Substances 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 241000233866 Fungi Species 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 11
• 125000004076 pyridyl group Chemical class 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 230000008635 plant growth Effects 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 238000012876 topography Methods 0.000 claims 1
• 241000196324 Embryophyta Species 0.000 description 100
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• 239000002904 solvent Substances 0.000 description 67
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
• 239000011737 fluorine Substances 0.000 description 53
• 229910052731 fluorine Inorganic materials 0.000 description 53
• 239000000203 mixture Substances 0.000 description 50
• 239000002253 acid Substances 0.000 description 48
• 239000000126 substance Substances 0.000 description 48
• 239000003995 emulsifying agent Substances 0.000 description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 125000001153 fluoro group Chemical group F* 0.000 description 36
• 241000894007 species Species 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
• 239000011593 sulfur Substances 0.000 description 34
• 229910052717 sulfur Inorganic materials 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• 239000011230 binding agent Substances 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 32
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 230000003993 interaction Effects 0.000 description 26
• 150000002148 esters Chemical class 0.000 description 25
• 239000000463 material Substances 0.000 description 25
• 230000000694 effects Effects 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 238000002360 preparation method Methods 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• 125000004093 cyano group Chemical group *C#N 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 239000008187 granular material Substances 0.000 description 17
• 239000002689 soil Substances 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 239000012141 concentrate Substances 0.000 description 16
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 238000011160 research Methods 0.000 description 15
• 239000002023 wood Substances 0.000 description 15
• 239000000417 fungicide Substances 0.000 description 14
• 239000002917 insecticide Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 241000238631 Hexapoda Species 0.000 description 13
• 150000002170 ethers Chemical class 0.000 description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• 229910052708 sodium Inorganic materials 0.000 description 13
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 12
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
• 235000005822 corn Nutrition 0.000 description 12
• 230000034994 death Effects 0.000 description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 241000700605 Viruses Species 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• 239000011591 potassium Substances 0.000 description 11
• 229910052700 potassium Inorganic materials 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
• 150000001298 alcohols Chemical class 0.000 description 10
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
• 244000005700 microbiome Species 0.000 description 10
• 229920005989 resin Polymers 0.000 description 10
• 239000011347 resin Substances 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• NTVKSUPEUFXUGS-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)acetic acid Chemical class OC(=O)CC=1C=CNN=1 NTVKSUPEUFXUGS-UHFFFAOYSA-N 0.000 description 9
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• 241000238876 Acari Species 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
• 239000003513 alkali Substances 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 239000000969 carrier Substances 0.000 description 9
• 230000006378 damage Effects 0.000 description 9
• 239000000975 dye Substances 0.000 description 9
• 239000000839 emulsion Substances 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 238000012545 processing Methods 0.000 description 9
• 108090000623 proteins and genes Proteins 0.000 description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
• 235000010469 Glycine max Nutrition 0.000 description 8
• 244000068988 Glycine max Species 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 150000001491 aromatic compounds Chemical class 0.000 description 8
• 239000002270 dispersing agent Substances 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 238000002156 mixing Methods 0.000 description 8
• 239000003960 organic solvent Substances 0.000 description 8
• 239000003973 paint Substances 0.000 description 8
• 239000002798 polar solvent Substances 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 125000001544 thienyl group Chemical group 0.000 description 8
• 239000008096 xylene Substances 0.000 description 8
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
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• 238000009835 boiling Methods 0.000 description 7
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• 239000003054 catalyst Substances 0.000 description 7
• 239000010949 copper Substances 0.000 description 7
• 229910052802 copper Inorganic materials 0.000 description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
• 150000002825 nitriles Chemical class 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 235000011181 potassium carbonates Nutrition 0.000 description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 description 7
• 125000006413 ring segment Chemical group 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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• KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 6
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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 6
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• 244000061176 Nicotiana tabacum Species 0.000 description 6
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• 125000001072 heteroaryl group Chemical group 0.000 description 6
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• 238000007654 immersion Methods 0.000 description 6
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• 150000002576 ketones Chemical class 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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• 239000000370 acceptor Substances 0.000 description 4
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