BR0209050B1 - azóis de ação inseticida, processo para produção e uso dos mesmos, bem como agentes para combate de pragas animais e produção dos referidos agentes. - Google Patents

Info

Publication number

BR0209050B1

BR0209050B1 BRPI0209050-3A BR0209050A BR0209050B1 BR 0209050 B1 BR0209050 B1 BR 0209050B1 BR 0209050 A BR0209050 A BR 0209050A BR 0209050 B1 BR0209050 B1 BR 0209050B1

Authority

BR

Brazil

Prior art keywords

spp

formula

methyl

compounds

agents

Prior art date

2001-04-20

Links

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• 238000000034 method Methods 0.000 title claims description 24
• 241001465754 Metazoa Species 0.000 title claims description 16
• 241000607479 Yersinia pestis Species 0.000 title claims description 16
• 238000004519 manufacturing process Methods 0.000 title claims description 11
• 230000000749 insecticidal effect Effects 0.000 title description 3
• 150000003851 azoles Chemical class 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
• 150000001875 compounds Chemical class 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 239000003153 chemical reaction reagent Substances 0.000 claims description 25
• 239000003795 chemical substances by application Substances 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 19
• 239000000460 chlorine Chemical group 0.000 claims description 18
• 229910052801 chlorine Chemical group 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 241000238631 Hexapoda Species 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 241000239223 Arachnida Species 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 241000244206 Nematoda Species 0.000 claims description 5
• 238000006396 nitration reaction Methods 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 244000078703 ectoparasite Species 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 101000989653 Homo sapiens Membrane frizzled-related protein Proteins 0.000 claims description 2
• 102100029357 Membrane frizzled-related protein Human genes 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 239000004094 surface-active agent Substances 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
• -1 Bicyclic azole derivatives Chemical class 0.000 abstract description 75
• 238000002360 preparation method Methods 0.000 abstract description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 8
• 125000003118 aryl group Chemical group 0.000 abstract description 5
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract description 2
• 125000002619 bicyclic group Chemical group 0.000 abstract 1
• 150000002462 imidazolines Chemical class 0.000 abstract 1
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• 238000009835 boiling Methods 0.000 description 9
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• 230000003373 anti-fouling effect Effects 0.000 description 7
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• 230000000694 effects Effects 0.000 description 7
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• 239000011593 sulfur Substances 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• 241000255925 Diptera Species 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 241000258242 Siphonaptera Species 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 229940052303 ethers for general anesthesia Drugs 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• HKSZSGAPTPXYTI-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=C(Cl)N=C1 HKSZSGAPTPXYTI-UHFFFAOYSA-N 0.000 description 6
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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• 241000257303 Hymenoptera Species 0.000 description 5
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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• 239000007788 liquid Substances 0.000 description 5
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• 229910052757 nitrogen Inorganic materials 0.000 description 5
• CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 5
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• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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• 125000003545 alkoxy group Chemical group 0.000 description 4
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