BRPI0716262A2 - (heteroaril)-alquil-sulfilminas n-substituÍdas inseticidas - Google Patents
(heteroaril)-alquil-sulfilminas n-substituÍdas inseticidas Download PDFInfo
- Publication number
- BRPI0716262A2 BRPI0716262A2 BRPI0716262-6A BRPI0716262A BRPI0716262A2 BR PI0716262 A2 BRPI0716262 A2 BR PI0716262A2 BR PI0716262 A BRPI0716262 A BR PI0716262A BR PI0716262 A2 BRPI0716262 A2 BR PI0716262A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkenyl
- alkyl
- insecticides
- formula
- haloalkyl
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 10
- 239000002917 insecticide Substances 0.000 title description 58
- 241000238631 Hexapoda Species 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 30
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000000415 inactivating effect Effects 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 6
- -1 6-substituted pyridin-3-yl Chemical group 0.000 description 129
- 239000004009 herbicide Substances 0.000 description 68
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 43
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000003986 organophosphate insecticide Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 14
- 241000607479 Yersinia pestis Species 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 241001124076 Aphididae Species 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 150000003568 thioethers Chemical class 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 241000721621 Myzus persicae Species 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000073 carbamate insecticide Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000003359 percent control normalization Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 241001600408 Aphis gossypii Species 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- 150000002081 enamines Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000002949 juvenile hormone Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002728 pyrethroid Substances 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- 241000193388 Bacillus thuringiensis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ODOSVAWLEGXOPB-UHFFFAOYSA-N Dinocton 6 Chemical compound COC(=O)OC1=C(CCCCCC(C)C)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ODOSVAWLEGXOPB-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001356 alkyl thiols Chemical class 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229930014550 juvenile hormone Natural products 0.000 description 3
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 3
- LFDDUUFFHPNIPZ-UHFFFAOYSA-N methyl n-[4-[[2-(4-chloro-2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C LFDDUUFFHPNIPZ-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- DQMRRIVHEYGQQG-DTWKUNHWSA-N (1r,2s)-2-(6-chloropyridin-3-yl)cyclopentan-1-ol Chemical compound O[C@@H]1CCC[C@H]1C1=CC=C(Cl)N=C1 DQMRRIVHEYGQQG-DTWKUNHWSA-N 0.000 description 2
- VDXWCRIARMBDOX-UHFFFAOYSA-N (4,6-dichloropyridin-3-yl)methanol Chemical compound OCC1=CN=C(Cl)C=C1Cl VDXWCRIARMBDOX-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- ZPWVMEBCBJNTNY-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)cyclopentan-1-ol Chemical compound C=1C=C(Cl)N=CC=1C1(O)CCCC1 ZPWVMEBCBJNTNY-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- PZHIYZLLIBBPFK-UHFFFAOYSA-N 2,4-dichloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CN=C(Cl)C=C1Cl PZHIYZLLIBBPFK-UHFFFAOYSA-N 0.000 description 2
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 2
- NQPBIEURRQSGQI-UHFFFAOYSA-N 2-(1,1-difluoroethyl)-5-methylpyridine Chemical compound CC1=CC=C(C(C)(F)F)N=C1 NQPBIEURRQSGQI-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- UXXLFUVYILHKLO-UHFFFAOYSA-N 2-methoxyethylmercury Chemical compound COCC[Hg] UXXLFUVYILHKLO-UHFFFAOYSA-N 0.000 description 2
- SOPHXJOERHTMIL-UHFFFAOYSA-N 3-methyl-4,6-dinitro-2-propan-2-ylphenol Chemical compound CC(C)C1=C(C)C([N+]([O-])=O)=CC([N+]([O-])=O)=C1O SOPHXJOERHTMIL-UHFFFAOYSA-N 0.000 description 2
- HYAAZWJMWVJCNF-UHFFFAOYSA-N 3-methylidenethiolane Chemical compound C=C1CCSC1 HYAAZWJMWVJCNF-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- PHXBEXGUYNSUFI-UHFFFAOYSA-N 5-(1-bromoethyl)-2-(trichloromethyl)pyridine Chemical compound CC(Br)C1=CC=C(C(Cl)(Cl)Cl)N=C1 PHXBEXGUYNSUFI-UHFFFAOYSA-N 0.000 description 2
- XDXFXDNITMXZGJ-UHFFFAOYSA-N 5-(1-methylsulfanylethyl)-2-(trichloromethyl)pyridine Chemical compound CSC(C)C1=CC=C(C(Cl)(Cl)Cl)N=C1 XDXFXDNITMXZGJ-UHFFFAOYSA-N 0.000 description 2
- MKTJGBDQMYPEFB-UHFFFAOYSA-N 5-(thiolan-3-yl)-2-(trifluoromethyl)pyridine Chemical compound C1=NC(C(F)(F)F)=CC=C1C1CSCC1 MKTJGBDQMYPEFB-UHFFFAOYSA-N 0.000 description 2
- QQOGZMUZAZWLJH-UHFFFAOYSA-N 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-n-ethylsulfonyl-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)CC)=CC(OC=2C(=CC(=CC=2F)C(F)(F)F)Cl)=C1 QQOGZMUZAZWLJH-UHFFFAOYSA-N 0.000 description 2
- OHVLWPYQADZCNA-UHFFFAOYSA-N 6-[chloro(difluoro)methyl]pyridine-3-carbonitrile Chemical compound FC(F)(Cl)C1=CC=C(C#N)C=N1 OHVLWPYQADZCNA-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 241001600407 Aphis <genus> Species 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
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- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- VHXDHGALQPVNKI-UHFFFAOYSA-N thiadiazol-4-ylurea Chemical compound NC(=O)NC1=CSN=N1 VHXDHGALQPVNKI-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical group CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- ITHPEWAHFNDNIO-UHFFFAOYSA-N triphosphane Chemical compound PPP ITHPEWAHFNDNIO-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
(HETEROARIL)-ALQUIL-SULFILIMINAS N-SUBSTITUIDAS INSETICIDAS. A invenção refere-se a (heteroaril)-alquil-sulfiliminas N- 5 substituidas que são eficazes em controlar insetos.
Description
Relatório Descritivo da Patente de Invenção para "(HETEROA- RIL)-ALQUIL-SULFILIMINAS N-SUBSTITUÍDAS INSETICIDAS".
Este pedido de patente reivindica o benefício do pedido de pa- tente provisório n9 de série US 60/841.934 depositado em 12 de setembro de 2006.
A presente invenção refere-se a (heteroaril)-alquil-sulfiliminas N- substituídas inusitadas e seu uso no controle de insetos, particularmente afidídeos e outros insetos sugadores, bem como certos outros invertebrados. Esta invenção inclui também novos procedimentos sintéticos para preparar os compostos, composições pesticidas que contêm os compostos, e méto- dos para controlar insetos usando os compostos.
Há uma necessidade aguda de se obter novos inseticidas. Os insetos estão desenvolvendo resistência aos inseticidas em uso corrente. Pelo menos 400 espécies de artrópodes são resistentes a um ou mais inse- ticidas. O desenvolvimento de resistência a alguns inseticidas mais antigos, tais como DDT, os carbamatos, e os organofosfatos, é bem conhecido. En- tretanto, a resistência se desenvolveu mesmo a alguns dos inseticidas pire- tróides mais novos. Portanto, existe uma necessidade de se obter novos in- seticidas, e particularmente compostos que têm modos de ação novos ou atípicos.
Esta invenção refere-se a compostos úteis para o controle de insetos, especialmente úteis para o controle de afidídeos e outros insetos sugadores. Mais especificamente, a invenção refere-se a compostos da fór- mula (I)
h^vr"
I N-Q
α>
em que
Het representa:
^
N N Ν" X N X representa halogênio, alquila de CrC4, halo-alquila de C1-C4, alquenila de C2-C4, alquimia de C2-C4, halo-alquenila de C2-C4, alcóxi de C1- C4, halo-alcóxi de CrC4, CN, NO2, SOmR6, onde m é um número inteiro en- tre Oe 2, COOR4 ou CONR4R5;
Y representa hidrogênio, halogênio, alquila de Ci-C4, halo-alquila
de Ci-C4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, alcóxi de C1-C4, halo-alcóxi de Ci-C4l CN, NO2, SOmR1, onde m é um núme- ro inteiro entre O e 2, COOR4, CONR4R5, arila ou heteroarila;
Z representa halo-alquila de Ci-C4, alquenila de C2-C 4, alquinila de C2-C4, halo-alquenila de C2-C4l halo-alcóxi de C1-C4, CN, NO2, SOmR1, onde m é um número inteiro entre O e 2, COOR4 ou CONR4R5;
N é um número inteiro entre O e 3;
L representa uma ligação simples, -CH2-, ou -CH(CH2)p-, onde ρ é um número inteiro entre 1 e 3, e R11 S e L ou R2, L e o carbono comum ao qual eles estão anexados são juntados para representar um anel com 4, 5 ou 6 membros e até, porém não mais do que 1 heteroátomo;
R1 representa alquila de C1-C4, halo-alquila de C1-C4, alquenila de C3-C6, alquinila de C3-C6l halo-alquenila de C3-C6, aril-alquila, hetaroaril- alquila, ou, alternativamente, é juntado com L ou R2 para formar um anel com 4, 5, ou 6 membros, saturado;
R2 e R3 representam independentemente hidrogênio, halogênio, alquila de C1-C4, halo-alquila de C1-C4l alquenila de C2-C4l alquinila de C2- C4, halo-alquenila de C2-C4l alcóxi de C1-C4, halo-alcóxi de C1-C4, CN, SO- mR6, onde m é um número inteiro entre 0 e 2, COOR41 CONR4R51 aril-alquila ou heteroaril-alquila, ou, alternativamente, R2 e R3 e o carbono comum ao qual eles estão anexados formam um anel com 3 a 6 membros, ou R2 e R3 juntados formam um anel com 4, 5, ou 6 membros, saturado; R4 e R5 representam independentemente hidrogênio, alquila de
C1-C4, halo-alquila de C1-C4, alquenila de C3-C6, alquinila de C3-C6, halo- alquenila de C3-C6,arila, heteroarila, aril-alquila ou heteroaril-alquila;
R6 representa alquila de C1-C4, halo-alquila de C1-C4, alquenila de C3-C6, alquinila de C3-C6, halo-alquenila de C3-C6, aril-alquila, heteroaril- alquila; e
Q representa NO2 ou CN.
Os compostos da fórmula (I) preferidos incluem as seguintes
classes:
(1) Compostos da fórmula (I) nos quais Het é piridin-3-ila substi- tuída na posição 6 ou tiazol-5-ila substituída na posição 2, e onde Z é halo-
alquila de Ci-C2 e Y é hidrogênio;
(2) Compostos da fórmula (I) nos quais R2 e R3 são como defini- dos anteriormente, R1 é metila, η é 1, e L é uma ligação simples, tendo a estrutura:
R1
R3 N-Q
(3) Compostos da fórmula (I) nos quais η é 1, R1, S e L juntados
foram um anel-padrão com 4, 5, ou 6 membros, de tal modo que L seja - CH(CH2)p-, e R1 seja -CH2-, tendo a estrutura:
Ha d
N—Q
(4) Compostos da fórmula (I) nos quais η é O, R1, S e L juntados foram um anel-padrão com 4, 5, ou 6 membros, de tal modo que L seja - CH(CH2)p-, e R1 seja -CH2-, tendo a estrutura:
Hcl-
L
(5) Compostos da fórmula (I) nos quais Q é CN.
Os versados nessas técnicas devem avaliar que os compostos mais preferidos são geralmente aqueles que compreendem combinações das classes preferidas acima.
A invenção fornece também novos processos para preparar compostos da fórmula (I), bem como novas composições e métodos de uso, que serão discutidos detalhadamente abaixo.
Neste relatório descritivo inteiro, todas temperaturas são forneci- das em graus Celsius, e todas porcentagens são porcentagens em peso, a menos que diferentemente assinalado.
Os termos "alquila", "alquenila", "alquinila", bem como os termos derivados tais como "alcóxi", "acila", "alquil-tio", "aril-alquila", "heteroaril- alquila" e "alquil-sulfonila", como aqui utilizados, incluem dentro do seu âmbi- to grupamentos com cadeia linear, ramificada e cíclica. Assim sendo, os grupos alquila típicos são metila, etila, 1-metil-etila, propila, 1,1-dimetil-etila, e ciclo-propila. A menos que diferentemente especificado, cada um deles pode ser não-substituído ou substituído com um ou mais substituintes sele- cionados, porém sem limitações, entre halogênio, hidroxila, alcóxi, alquil-tio, acila de C1-C6, formila, ciano, arilóxi, ou arila, desde que os substituintes se- jam estericamente compatíveis e as regras de ligação química e energia de deformação sejam satisfeitas. Os termos "halo-alquila" e "halo-alquenila" incluem grupos alquila e alquenila substituídos com entre um e o número máximo possível de átomos de halogênio, estando incluídas todas combina- ções de halogênios. O termo "halogênio" ou "halo" inclui flúor, cloro, bromo e iodo, sendo preferido o preferido. Os termos "alquenila" e "alquinila" preten- dem incluir uma ou mais ligações insaturadas.
O termo "arila" refere-se a um grupo fenila, indanila ou naftila. O termo "heteroarila" refere-se a um anel aromático com 5 ou 6 membros, con- tendo um ou mais heteroátomos, a saber, Ν, O ou S; estes anéis heteroaro- máticos podem estar fundidos a outros sistemas aromáticos. Os substituin- tes arila ou heteroarila podem ser não-substituídos ou substituídos com um ou mais substituintes selecionados entre halogênio, hidroxila, nitro, ciano, arilóxi, formila, alquila de C1-C6, alquenila de CrC6, alquinila de Ci-C6, alcóxi de Ci-C6, alquila de CrC6 halogenada, alcóxi de CrC6 halogenado, acila de CrC6, alquil-tio de C1-C6, alquil-sulfinila de C1-C6, alquil-sulfonila de Ci-C6, arila, 0C(0)-alquila de C1-C6, NHC(0)-alquila de C1-C6, C(O)OH, CO(O)- alquila de C1-C6, C(O)NH2, C(0)NH-alquila de C1-C6, ou C(0)N-(alquila de CrC6)2, desde que os substituintes sejam estericamente compatíveis e as regras de ligação química e energia de deformação sejam satisfeitas.
Os compostos desta invenção podem existir como um ou mais estereoisômeros. Os vários estereoisômeros incluem isômeros geométricos, diastereoisômeros e enantiômeros. Assim sendo, os compostos da presente invenção incluem misturas racêmicas, estereoisômeros individuais e mistu- ras opticamente ativas. Os versados nessas técnicas devem avaliar que um estereoisômero pode ser mais ativo do que outros. Os estereoisômeros indi- viduais e as misturas opticamente ativas podem ser obtidos por procedimen- tos sintéticos seletivos, por procedimentos sintéticos convencionais usando materiais de partida não-resolvidos ou por procedimentos de resolução con- vencionais.
Os compostos da fórmula (I), onde Q é NO2 e R1, R2, R3, η e L são como definidos anteriormente, podem ser preparados pelo método ilus- trado no Esquema A. Esquema A
NO- S—L—(CRW)e-Het ■ jj,
| , "^S—L—(CR7R5) —He»
R· «íNNOl |
<A) Ac2O Ri
(D
Na etapa "a" do Esquema A, o sulfeto de fórmula (A) é reagido com nitramida na presença de anidrido acético para produzir a sulfilimina (I) (Shitov, O.P.; Seleznev, A.P.; Tartakovski, V.A., lnst. Org. Kim. im. Zelinsko- go, Moscou, URSS, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1991), (5), 1237-8).
Os compostos da fórmula (Ia), onde Q é CN e Het, R1, R2, R31 η e L são como definidos anteriormente, podem ser preparados pelo método ilustrado no Esquema B. Consequentemente, o sulfeto precursor é oxidado com diacetato de iodo-benzeno na presença de cianamida a O 0C, para dar a sulfilimina (Ia). A reação pode ser conduzida em um solvente aprótico polar, tal como CH2CI2. Esquema B
.CN
S—L—(CR2R3)n —Hei * j?
J Phl(OAc)lt. NH2CN [
R
(A) R (Ia)
L—(CR2R5)n —Het
Os sulfetos precursores (A) podem, por sua vez, ser preparados
de diferentes maneiras, como ilustrado nos Esquemas C, D, E, F e G.
No Esquema C, o sulfeto da fórmula (A1), onde L é uma ligação simples, η é 1, R3 = H, e R1, R2 e Het são como definidos anteriormente, po- de ser preparado a partir de halogenetos da fórmula (D) por substituição nu- cleofílica com o sal de sódio de um alquil-tiol. Esquema C
R2 R2
^—Het —;—- ^—Het
XR1SNa ρ ι π
X o α. Br, ar I K1 o
(D) (A1)
No Esquema D, o sulfeto da fórmula (A2), onde L é uma ligação simples, η é 3, R3 = H, e R1, R2 e Het são como definidos anteriormente, po- de ser preparado a partir do cloreto da fórmula (E) reagindo com malonato de metila monossubstituído na posição 2, na presença de uma base, tal co- mo t-butóxido de potássio, para produzir o malonato dissubstituído na posi- ção 2,2, hidrólise sob condições básicas, para formar um diácido, descarbo- xilação do diácido aquecendo, para dar um monoácido, redução do monoá- cido com complexo de borano/tetraidrofurano, para produzir um álcool, tosi- lação do álcool com cloreto de toluenossulfonila (cloreto de tosila) na pre- sença de uma base, tal como piridina, para dar um tosilato, e substituição do tosilato pelo sal de sódio do tiol desejado. Esquema D
-Het __ ____ /-Het
MeOjC
C1CH, -Het
(H)
KCMBu
RsCH(OOjMe),
Λ
R1
UOH
HO2C
HO2C
HO3C
Het
BH3THP
HQ
Ri
Het
J)TjO. Py 2) NaSR1
R* R1-S
Het
RJ
(A2)
R2
No Esquema Ε, o sulfeto da fórmula (A3), onde L é uma ligação simples, η é 2, R3 = H, e R1, R2 e Het são como definidos anteriormente, po- de ser preparado a partir da nitrila da fórmula (F) por desprotonação com uma base forte e alquilação com um iodeto de alquila, para dar a nitrila Π- ΙΟ alquilada na presença de um ácido forte, tal como HCI, para dar um ácido, redução do ácido com complexo de borano/tetraidrofurano, para produzir um álcool, tosilação do álcool com cloreto de tosila na presença de uma base, tal como piridina, para dar um tosilato, e substituição do tosilato pelo sal de sódio do tiol desejado. Esquema E
R>
R1
NC
y—Het
(F) RJ.
-Het
HO-
tase R1I
TlCUPy
NC
Het
HO
HO1C
Hat
BH1THF
Sf
NaSR1
R1
-Hct
(A3)
20
No Esquema F, o sulfeto da fórmula (A4), onde η é O, R1 é CH2, L é -CH(CH2)p-, onde ρ é 2 ou 3, e em conjunto com R1, S e L formam um anel com 5 ou 6 membros, e Het é como definido anteriormente, pode ser preparado a partir de tetraidrotiofeno (p = 2) ou sulfeto de pentametileno (p = 3) (G). A cloração do material de partida sulfeto cíclico com N-cloro- succinimida em benzeno, e em seguida, alquilação com certos heterociclos Iitiados ou reagentes de Grignard pode levar aos sulfetos (A4) desejados com rendimento satisfatório. Esquema F
NCS. S Het-M-Xe s
(G) (A4)
Um protocolo mais eficiente para obter os sulfetos cíclicos da
fórmula (A4) está ilustrado no Esquema G1 onde Het é uma piridin-3-ila subs- tituída na posição 6, e Z é como definido anteriormente. Consequentemente, tiouréia é adicionada a uma cloro-metil-piridina substituída, a qual, depois da hidrólise e alquilação com o bromo-cloro-alcano apropriado (p = 1, 2 ou 3) sob condições de base aquosa, produz o sulfeto (Η). A subsequente cicliza- ção de (H) na presença de uma base, tal como t-butóxido de potássio, em um solvente aprótico polar, tal como THF, produz o sulfeto cíclico (A4). Esquema G
TW1HMPA1Ut:
(A4) Wherep= l.2,or3
Certos sulfetos da fórmula (Ai), onde Het é uma piridin-3-ila substituída, e Z é como definido anteriormente, e R1, R2 = CH3, podem ser preparados alternativamente por intermédio dos métodos ilustrados no Es- quema H. Consequentemente, a enona apropriada é acoplada com dimetil- amino-acrilonitrila e ciclizada com acetato de amônio em DMF, para produzir a nicotinonitrila substituída na posição 6 correspondente. O tratamento com brometo de metil-magnésio, redução com boridreto de sódio, cloração com cloreto de tionila, e substituição nucleofílica com o sal de sódio de um alquil- tiol, produz os sulfetos (Ai) desejados. Esquema H
,CN
R1
nr JfytO
β. wíuam qW 2 N THfitijO Z · N
,00OC I NaBH4
I McOH
Rj R1 * R1
soa, ^jÇj-^OH
/y^"' .»»*- JfTla
& N ElOH. R.T. Z N
CH^Hj. It
ElOH1R-T.
(A1)
Uma variação do Esquema H está ilustrada no Esquema I, onde as enaminas, formadas a partir da adição de uma amina, por exemplo, pirro- lidina, com o aduto de Michael de certos sulfetos com aldeídos □ ,□- insaturados adequadamente substituídos, são acopladas com enonas substi- tuídas e ciclizadas com acetato de amônio em CH3CN, para produzir os sul- fetos (A1) desejados, onde R1, R2, R3 e Z são como definidos anteriormente. Esquema I
rKs.h Λ X JS<R>
H JC.. V—/ rr^S -,"^n N HOAc rT^V^S
r3__ λl J=L Cs'"-^- NH-OAc /S^i
Wn KJluene CHjOI Z
. IOO0C (A1)
Uma variação deste método, ilustrada no Esquema J, pode ser usada para preparar sulfetos de piridila cíclicos (A5), onde η = 1, L = -(CH2)-, e R1 e R2 se ligam para formar um anel com 5 membros. Consequentemen- te, a reação de tetraidrotiofen-3-ona com trifenil-fosfina e carbonato de dime- tila produz a olefina correspondente, que é então hidroformilada com hidro- gênio e monóxido de carbono na presença de um catalisador de ródio, para produzir o aldeído (N). As etapas remanescentes para converter o aldeído em sulfeto (A5) seguem o mesmo protocolo descrito anteriormente no Es- quema I. Esquema J
ô
/—\ Ph3P ι—. Hz. σο r—\ w
Oisi^vXs (MeO)2CO -CSS=Ns^s 700 P8' w " Rh/Xantphos (caí) I
O 10
O
CH1CN
NH4OAc CHiCN
(A5)
No Esquema Κ, os sulfetos da fórmula (A6), onde R1 e Z são como definidos anteriormente, η = 1 e L, R2, e o carbono comum ao qual eles estão anexados são ligados para formar um anel com 4, 5 ou 6 mem- bros (x = 0-2), podem ser preparados a partir de 5-bromo-pirídinas substituí- das na posição 2 por intermédio de uma troca de metal halogênio com Grig- nard isopropila ou n-butil-lítio, e em seguida, adição de cetona cílcica, tal como ciclo-pentanona (x = 1), desidratação para dar a olefina sob condições ácidas, hidroboração (borano em tetraidrofurano), clivagem oxidativa (hidró- xido de sódio e peróxido de hidrogênio), conversão do álcool resultante e um grupamento facilmente deslocável, tal como um grupo metanossulfonila (pe- lo tratamento com cloreto de metanossulfonila e trietil-amina), e finalmente substituição nucleofílica com o sal de sódio de um alquil-tiol. Esquema K
OOMflPr [j
_ nr n-BuLJ
Xf
2)
N
O 3» H♦
obh/THF
2) NeOH1HA
3) MsCT, TEA
4) NaSMe, ElOH
"R1
(Ai)
EXEMPLOS Exemplo I Preparação
de
cnifanilirlpnodanamida (1)
F,C
{1-f6-(triflúor-met^0-Piridin-3-in-metil)-λ4
í
N
N-CN
(1)
(A) (A)
Adicionou-se tiometóxido de sódio em uma parcela (1,8 g, 26 mmols) a uma solução de 3-cloro-metil-6-(triflúor-metil)-piridina (5,1 g, 26 mmols) em sulfóxido de dimetila (DMSO; 20 ml_). Uma reação exotérmica violenta foi observada, a qual resultou na reação se tornar escura. A reação foi agitada por 1 h, e depois adicionou-se lentamente mais tiometóxido de sódio (0,91 g, 13 mmols). A reação foi agitada de um dia para o outro, após o que ela foi vertida sobre H2O e foram adicionadas várias gotas de HCI con- centrado. A mistura foi extraída com Et2O (3 χ 50 ml_) e as camadas orgâni- cas foram combinadas, lavadas com salmoura, secadas com MgS04, filtra- das e concentradas. O produto bruto foi purificado por cromatografia (Prep 500, 10% de acetona/hexanos, v/v) para produzir o sulfeto (A) como um óleo amarelo-pálido (3,6 g, 67%). 1H RMN (300 MHz, CDCI3) δ 8,6 (s, 1H), 7,9 (d, 1H), 7,7 (d, 1H), 3,7 (s, 2H), 2,0 (s, 3H); GC-MS: massa calculada para C8H8F3NS [M]+ 207. Encontrado 207. (B)
β^γ^δ"0"5 HjNCN, PM<OA^
A CH3CIrO-C ^J N^__
F1C N FiC N CN
<I4*>
CA) (!)
Adicionou-se diacetato de iodo-benzeno (11,0 g, 34 mmols) de uma só vez a uma solução do sulfeto (A) (3,5 g, 17 mmols) e cianamida (1,4 mg, 34 mmols) em CH2CI2 (30 ml_) a 0 0C. A reação foi agitada por 30 min e depois deixada aquecer até a temperatura ambiente durante a noite inteira. A mistura foi diluída com CH2CI2 (50 ml_) e lavada com H2O. A camada a- quosa foi extraída com acetato de etila (4 χ 50 mL), e as camadas em CH2CI2 e acetato de etila combinadas foram secadas com MgSO4 e concen- tradas. O produto bruto foi triturado com hexanos e purificado por cromato- grafia (Chromatotron, 60% de acetona/hexanos, v/v) para produzir a sulfili- mina (1) como uma goma amarela (0,60 g, 14%). IV (película) 3.008, 2.924, 2.143, 1.693 cm1; 1H RMN (300 MHz, CDCI3) δ 8,8 (s, 1H), 8,0 (d, 1H), 7,8 (d, 1H), 4,5 (d, 1 H), 4,3 (d, 1H), 2,9 (s, 3H); LC-MS (ESI): massa calculada para C9H9F3N3S [M+H]+ 248,04. Encontrado 248. Exemplo Il
Preparação de (1 -í6-rcloro-(diflúor)-metin-Diridin-3-il}-etil)-(metil)-À4- sulfanilidenocianamida (2)
N-CN (2)
(A)
FWF NH4OAc ^Tcn
aW -5-: -L^ CINII
Ps IOluene DMF IOO0C
Oioluene DMF ·
ΙΛΛΙΟ F F
(A)
(3E)-1-Cloro-4-etóxi-1,1-diflúor-but-3-en-2-ona (7,36 g, 40 mmols) foi dissolvida em tolueno anidro (40 mL) e tratada com 3-dimetil- amino-acrilonitrila (4,61 g, 48 mmols) à temperatura ambiente. A solução foi aquecida a 100 0C por 3,5 h. O solvente foi então removido sob pressão re- duzida e a mistura remanescente foi redissolvida em dimetil-formamida (DMF; 20 mL), tratada com acetato de amônio (4,62 g, 60 mmols) e agitada à temperatura ambiente de um dia para o outro. Adicionou-se água à mistura reativa e a mistura resultante foi extraída com éter:CH2CH2 (1:2, v/v) duas vezes. As camadas orgânicas combinadas foram lavadas com salmoura, secadas, filtradas e concentradas. O resíduo foi purificado em sílica-gel para dar 3,1 g de 6-[cloro-(diflúor)-metil]-nicotinonitrila (A) com um óleo de cor clara com 41% de rendimento. GC-MS: massa calculada para C7Hi3CIF2N2 [M]+ 188. Encontrado 188.
(B)
XN
•W
McMgBr
p p " THFZEt1O
(A) (B) A 6-[cloro-(diflúor)-metil]-nicotinonitrila (A) (3,0 g, 15,8 mmols) foi dissolvida em éter anidro (25 mL) e resfriada em um banho de gelo/água. Uma solução 3 M de brometo de metil-magnésio em hexano (6,4 mL, 19 mmols) foi adicionada através de uma seringa. Depois de terminada a adi- ção, a mistura foi agitada a 0 0C por 5 h e depois à temperatura ambiente por 10 h. A reação foi interrompida lentamente com solução aquosa de ácido cítrico 1 N a 0 0C, e a mistura resultante foi agitada à temperatura ambiente por 1 h. O pH foi ajustado de volta para pH 7 com solução aquosa saturada de NaHCO3. As duas fases foram separadas e a fase aquosa foi extraída com acetato de etila duas vezes. As camadas orgânicas combinadas foram lavadas com salmoura, secadas com Na2SO4 anidro, filtradas, e concentra- das. A mistura remanescente foi purificada em sílica-gel eluída com 15% de acetona em hexano (v/v), para dar 0,99 g do produto desejado, 1-{6-[cloro- (diflúor)-metil]-piridin-3-il}-etanona (B) como um óleo amarronzado com ren- dimento de 30%. GC-MS: massa calculada para C8H6CIF2NO [M]+205. En- contrado 205. (C)
Adicionou-se NaBH4 (0,16 g, 4,14 mmols) a uma solução de 1- {6-[cloro-(diflúor)-metil]-piridin-3-il}-etanona (B) (0,85 g, 4,14 mmols) em Me- OH (10 mL) a 0 0C. A mistura foi agitada por 30 min e adicionou-se uma so- lução aquosa 2 M de HCI até atingir pH 7. O solvente foi removido sob pres- são reduzida e a mistura remanescente foi extraída com CH2CI2 (2 χ 50 mL). As camadas orgânicas combinadas foram secadas com Na2SO4 anidro, fil- tradas, concentradas, e secadas sob vácuo, para dar 0,798 g de 1-{6-[cloro- (diflúor)-metil]-piridin-3-il}-etanol (C) analiticamente puro em GC-MS como um óleo amarelo com rendimento de 93%. GC-MS: massa calculada para C8H6CIF2NO [M]+207. Encontrado 207. (D) Adicionou-se cloreto de tionila (0,54 mL, 7,54 mmols) sob a for- ma de gotas à temperatura ambiente a uma solução de 1 -{6-[cloro-(diflúor)- metil]-piridin-3-il}-etanol (0,78 g, 3,77 mmols) em CH2CI2. Depois de 1 h, a reação foi interrompida lentamente com solução aquosa saturada de NaH- CO3 e as duas fases foram separadas. A camada orgânica foi secada com Na2SO4, filtrada, concentrada, secada sob vácuo, para dar 0,83 g de 2- [cloro-(diflúor)-metil]-5-(1-cloro-etil)-piridina (D) como um óleo marrom com rendimento de 98%, que foi usado diretamente na próxima etapa da reação. GC-MS: massa calculada para C8H7CI2F2N [M]+225. Encontrado 225.
(E)
Adicionou-se tiometóxido de sódio (0,52 g, 7,4 mmols) sob agi- tação em uma parcela a 0 0C a uma solução de 2-[cloro-(diflúor)-metil]-5-(1- cloro-etil)-piridina (D) (0,81 g, 3,6 mmols) em etanol (10 mL). Depois de 10 min, a mistura foi deixada aquecer até a temperatura ambiente e agitada de um dia para o outro. O solvente etanol foi então removido sob pressão redu- zida e o resíduo foi recolocado em éter/CH2CI2 e salmoura. As duas fases foram separadas e a fase aquosa foi extraída com CH2CI2 mais uma vez. A camada orgânica combinada foi secada com Na2SO4 anidro, filtrada, con- centrada, e purificada em sílica-gel, usando 5% de acetato de etila em hexa- no (v/v), para dar 0,348 g de 2-[cloro-(diflúor)-metil]-5-[1-(metil-tio)-etil]- piridina (E) com 40% de rendimento. GC-MS: massa calculada para C9H10CIF2NS [M]+237. Encontrado 237. (F) Cl
F F
Phl(OAc)1, NH2CN THF, 0 0C
F P
Il
CN
(E)
(2)
Adicionou-se diacetato de iodo-benzeno (0,44 g, 1,35 mmol) em
uma parcela a O 0C a uma solução de 2-[cloro-(diflúor)-metil]-5-[1-(metil-tio)- etilj-piridina (E) (0,32 g, 1,35 mmol) em tetraidrofurano (THF; 7 mL), sob agi- tação, e a mistura resultante foi agitada nessa temperatura por 1 h e depois à temperatura ambiente por 2 h. O solvente foi removido sob pressão redu- zida e a mistura resultante foi dissolvida em CH2CI2, lavada com salmoura semissaturada, secada com Na2SO4 anidro, filtrada, concentrada, e purifica- da em sólica-gel usando 50% de acetona em hexano (v/v), para dar 0,175 g de (1 -{6-[cloro-(diflúor)-metil]-piridin-3-il}-etil)-(metil)^4-sulfanilidenocianami- da (2) como um óleo amarelo-claro com 48% de rendimento. 1H RMN (300 MHz, CDCI3) δ 8,71 (d, J = 1,8 Hz, 1H), 7,91 (dd, J = 8,4 1,8 Hz, 1H), 7,78 (d, J = 8,4 Hz, 1H), 4,42 (q, J = 6,9 Hz, 1 H), 2,64 (s, 3H), 1,92 (d, J = 6,9 Hz, 3H); LC-MS: massa calculada para Ci0H10CIF2N3S [M+1]+ 278. Encontrado 278. Exemplo Ill
Preparação_de_(1 -f6-(tricloro-metil)-piridin-3-il1-etiD-(metil)^4-
sulfanilidenocianamida (3)
Uma mistura de ácido 5-etil-piridino-2-carboxílico (1,98 g, 13 mmols), dicloreto fenil-fosfônico (2,8 g, 14,3 mmols), e pentacloreto de fósfo- ro (7,7 g, 32 mmols) foi agitada e aquecida lentamente. Depois que um líqui-
(3)
(A)
(A) do amarelo límpido se formou, a mistura foi aquecida sob refluxo durante a noite inteira. Depois de resfriar, os voláteis foram removidos sob pressão reduzida. O resíduo foi vertido cuidadosamente sobre solução aquosa satu- rada de carbonato de sódio resfriada em um banho de gelo/água. A fase a- quosa foi então extraída com CH2CI2 duas vezes. As camadas orgânicas combinadas foram lavadas com salmoura, secadas com Na2S04 anidro, fil- tradas, concentradas e parcialmente purificadas e, sílica-gel eluída com 10% de EtOAc em hexano (v/v), para dar 2,7 g do produto que contém 5-etil-2- (tricloro-metil)-piridina e também 5-(1-cloro-etil)-2-(tricloro-metil)-piridina em uma razão aproximada de 3:1 (dados de GC1 massas calculadas para C8H8CI3N e C8H7CI4N [M]+ 223 e 257, respectivamente. Encontradas 223 e 257, respectivamente).
Uma mistura do produto bruto mencionado acima (2,6 g) em te- tracloreto de carbono (100 mL) foi tratada com cerca de 80% de N-bromo- succinimida (1,9 g, 11 mmols) e peróxido de benzoíla (0,66 g, 0,275 mmol) e refluxada de um dia para o outro. O sólido foi removido por filtração, o filtra- do foi concentrado e o resíduo resultante foi purificado em sílica-gel usando 4% de EtOAc em hexano (v/v), para dar 1,0 g do produto desejado, 5-(1- bromo-etil)-2-(tricloro-metil)-piridina (A) como um sólido amarelo. O rendi- mento combinado para as duas etapas foi de 25%. GC-MS: massa calculada para C8H7BrCI3N [M-1-CI]+ 266. Encontrado 266. (B)
MeSNa
.JDx
EtOH.rt
CljC' "N' CI3C
(A)
Uma solução de 5-(1-bromo-etil)-2-(tricloro-metil)-piridina (A) (0,95 g, 3,14 mmols) em etanol (15 mL) foi tratada com tiometóxido de sódio (0,44 g, 6,29 mmols) em parcelas a 0 0C. A mistura foi agitada à temperatura ambiente durante a noite inteira. O solvente etanol foi então removido sob pressão reduzida e o resíduo foi recolocado em CH2CI2 e salmoura. As duas fases foram separadas e a camada orgânica foi secada com Na2SO4 anidro, filtradas e concentradas. O resíduo foi purificado em sílica-gel usando 5% de 10
15
EtOAc em hexano (v/v), para dar 0,57 g da 5-[1-(metil-tio)-etil]-2-(tricloro- metil)-piridina parcialmente pura com 67% de rendimento bruto. GC-MS: massa calculada para C9HioCI3NS [M]+ 269. Encontrado 269. (C)
JQ^
CLC N
Phl(OAc)1, NH2CN
- N CN
20
'N' THFiO0C CljC' 'N'
(B) (3)
Adicionou-se diacetato de iodo-benzeno (0,75 g, 2,3 mmols) em uma parcela a uma solução de 5-[1-(metil-tio)-etil]-2-(tricloro-metil)-piridina (B) (0,55 g, 2,3 mmols) e cianamida (0,097 g, 2,3 mmols) em THF (7 mL) resfriada até 0 0C, sob agitação. A mistura resultante foi agitada a 0 0C por 1 h e depois à temperatura ambiente por 2 h. O solvente foi removido sob vá- cuo e a mistura resultante foi purificada em sílica-gel usando 50% de aceto- na em hexano (v/v), para dar 0,254 g de {1-[6-(tricloro-metil)-piridin-3-il]-etil}- (metil)-À4-sulfanilidenocianamida (3) como um sólido esbranquiçado com 40% de rendimento. 1H RMN para a mistura diastereoisomérica (300 MHz, de-acetona) δ 8,87 (s, 1H), 8,21-8,25 (m, 2H), 465-4,76 (m, 1H), 2,86-2,66 (m, 3H), 1,88-1,92 (m, 3H). Exemplo IV
Preparação_de_(1EH1 -(2-cloro-pirimidin-5-il)-etilHmetil)^4-
sulfanilidenocianamida (4)
CN
(A)
(4)
nbs,ccí4
(PhaD)1Ot (cai.)
Λ J
(A)
Uma solução de 2-cloro-5-etil-pirimidina (1,15 g, 8,1 mmols) em mL de tetracloreto de carbono foi tratada com N-bromo-succinimida (1,50 g, 8,4 mmols) e uma quantidade catalítica de peróxido de benzoíla, e a mis- tura foi aquecida até 75 0C. Depois de várias horas e mais catalisador, o ma- terial de partida tinha sido completamente consumido. O sólido foi removido e o filtrado foi concentrado sob pressão reduzida. O resíduo resultante foi purificado por cromatografia de coluna em sílica-gel, usando uma mistura de acetato de etila e éter de petróleo como solvente eluente. Os solventes fo- ram removidos sob pressão reduzida, para dar 0,64 g (36%) de 5-(1-bromo- etil)-2-cloro-pirimidina (A) como um líquido límpido. 1H RMN (CDCI3) δ 8,70 (s, 2H), 5,15 (q, J = 8,0 Hz1 1H), 2,10 (d, J = 8,0 Hz, 3H); GC-MS (FID) m/z 222 (M+). Parte do composto dibromo correspondente, 9,44 g (18%) tam- bém foi isolada como um sólido branco: ponto de fusão (p.f.) 84-85 0C; 1H RMN (CDCI3) δ 9,00 (s, 2H), 3,00 (s, 3H); LCMS (ESI) m/z 298 (M+H). (B)
?r MeSN· I
c,xr ^ cXX^
(A) (B)
A 2-cloro-5-[1-(metil-tio)-etil]-pirimidina (B) foi obtida como um xarope amarelo-pálido a partir do brometo (A), usando o mesmo procedi- mento descrito no Exemplo Ill (B) acima. 1H RMN (CDCI3) δ 8,60 (s, 2H), 3,85 (q, J = 8,0 Hz, 1H), 1,98 (s, 3H), 1,65 (d, J = 8,0 Hz, 3H); GCMS (FID m/z 188 (M+). (C)
| PW(OAc)1, I
jsj-^Y^S^ NHiCN ^isVX
Q^vN thf.ooc cr>i ncn
(B) <4)
O composto do título, (1E)-[1-(2-cloro-pirimidin-5-il)-etil]-(metil)-
X4-Sulfanilidenocianamida (4), foi obtido como um xarope laranja-pálido e uma mistura 2:1 de diastereoisômeros a partir do sulfeto (B), usando o mesmo procedimento descrito no Exemplo Ill (C) acima. Diastereoisômero principal: 1H RMN (CDCI3) δ 8,68 (s, 2H), 4,38 (q, J = 8,3 HZ, 1H), 2,68 (s, 3Η), 1,92 (d, J = 8,3 Hz, 3H); LC-MS (ESI) m/z 229 (M+H). Exemplo V
Preparação de (1 E)-metil-(f2-triflúor-metil)-1.3-tiazol-5-il1-metil)-À4- sulfanilidenocianamida (5)
F3cHSjíHC
N CN
(5)
(A)
NaSMe s
F3C-H J -~ F3C-<\ J
N aOH.rt N-1
(A) (B)
O 5-[(metil-tio)-metil]-2-(triflúor-metil)-1,3-tiazol (B) foi obtido co- mo um líquido laranja-pálido a partir de 5-(bromo-metil)-2-(triflúor-metil)-1,3- tiazol (A) (patente n- US 5.338.856) usando o mesmo procedimento descrito no Exemplo Ill (B). 1H RMN (CDCI3) δ 7,75 (s, 1H), 3,90 (s, 2H), 2,10 (s, 3H);
0 GC-MS (FID) m/z 213 (M+). (B)
J -^ fHJ β
N ΕιΟΗ,η N 1^CN
(B) (5)
A (1 E)-metil-{[2-triflúor-metil)-1,3-tiazol-5-il]-metilR4-sulfanili- denocianamida foi obtida como um xarope amarelo-pálido a partir do sulfeto (B) usando o mesmo procedimento descrito no Exemplo Ill (C) acima. 1H
1 RMN (CDCI3) δ 8,00 (s, 1H), 4,60 (s, 2H), 2,85 (s, 3H); LCMS (ESI) m/z 254 (M+H).
Exemplo Vl
Preparação de 3-f6-(triflúor-metil)-piridin-3-ill-tetraidro-1 H-U4-tien-1- ilidenocianamida (6)
CN
JCf^
F3C N
(6) (A)
DMC, PPh
DMC, PPh3
Tetraidrotien-3-ona (9,947 g, 97,37 mmols) foi colocada em uma
bomba Parr de 250 mL. Trifenil-fosfina (28,09 g, 108,0 mmols) foi adiciona- da, e em seguida, adicionou-se CH3I (0,30 mL, 4,8 mmols) e carbonato de dimetila (10,0 mL, 119 mmols). O reator foi purgado com nitrogênio e depois aquecido por 3 h a 175°C. A mistura reativa foi resfriada até a temperatura ambiente e purificada por destilação Kugelrohr, para dar 3-metileno- tetraidrotiofeno como um líquido incolor (7,65 g) que continha a olefina dese- jada junto com metanol e benzeno. A olefina desejada foi usada sem purifi- cação adicional. 1H RMN (CDCI3) δ 4,77 (m, 1H, H olefínico), 4,72 (m, 1H, H olefínico), 2,63 (t, J = 7 Hz, 2H, H5), 2,55 (s, 2H, H2), 2,41 (BR t, J = 7 Hz, 2H, H4). 13C(1H) RMN (CDCI3) δ 107,3 (CH2 olefínico), 36,7, 35,3, 30,4. GC- MS (El): 100 [M]+.
metanol) foi colocado em uma bomba Parr de 25 mL que continha uma barra de agitação magnética. Rh(CO)2(acac) (149 mg, 0,58 mmol) e 4,5-bis- (difenil-fosfino)-9,9-dimetil-xanteno (Xantphos) (355 mg, 0,61 mmol) foram adicionados como sólidos. O reator foi vedado e purgado com CO antes de pressurizar até 2,413 MPa (350 psi). Depois, adicionou-se hidrogênio para levar a pressão total até 4,826 MPa (700 psi). O reator foi aquecido até 80 0C sob agitação magnética por 14 h. A mistura reativa foi resfriada até a temperatura ambiente. A GC-MS indicou a presença de um único regioisô- mero de aldeído junto com benzeno e metanol. Nenhuma olefina de partida estava evidente. O solvente foi removido sob vácuo e o produto (tetraidroti- en-3-il-acetaldeído) foi isolado por destilação Kugelrohr (50 °C/0,01 mm)
(B)
5
3-Metileno-tetraidrotiofeno (5,88 g, como mistura com benzeno e como um líquido incolor (1,1 g). 1H RMN (acetona-d6) δ 9,76 (t, J = 1,4 Hz, 1H, CH2CHO), 2,97 (m, 1H), 2,83 (d, J = 5,7 Hz, 1H), 2,80 (d, J = 5,4 Hz, 1H), 2,62 (br s, 3H), 2,46 (m, 1H), 2,17 (m, 1H), 1,61 (m, 1H). GC-MS (El): 130 [m]+.
colocado em um frasco que foi purgado com nitrogênio. O frasco foi resfriado em um banho de gelo, e adicionou-se K2CO3 sólido (0,584 g, 4,23 mmols). A seguir, adicionou-se pirrolidina (1,70 ml_) na forma de gotas durante 5 min. O banho de gelo foi removido, e a mistura reativa foi agitada sob N2 por 20 h. A GC-MS indicou a formação pura da enamina desejada. O sólido foi lavado com quatro parcelas de 10 mL de éter. Os extratos etéreos combinados fo- ram evaporados sob vácuo, para dar a enamina intermediária como um óleo amarelo-claro (1,617 g). O 3-etóxi-2-triflúor-metil-propenal (1,634 g, 9,72 mmols) foi dissolvido em CH3CN anidra (5 mL) sob nitrogênio. A solução foi resfriada em um banho de gelo. Uma solução de enamina (1,617 g) em 2 mL de CH3CN foi adicionada na forma de gotas durante 10 min. O banho de ge- lo foi removido e a solução foi deixada aquecer até a temperatura ambiente e a agitação foi continuada por 2 h. Adicionou-se acetato de amônio (1,407 g, 18,25 mmols) e a mistura reativa foi refluxada sob nitrogênio por 1 h. A solução foi resfriada até a temperatura ambiente e a CH3CN foi evaporada sob vácuo. O óleo vermelho resultante foi purificado por cromatografia de coluna em sílica com hexano/acetato de etila, para produzir 5-tetraidrotien-3- il-2-(triflúor-metil)-piridina (1,08 g, 52,3% de rendimento) como um sólido cristalino laranja. 1H RMN (CDCI3) δ 8,68 (d, J = 1,6 Hz, 1H H6 de piridina), 7,83 (dd, J = 1,6, 8,0 Hz, 1H, H4 de piridina), 7,65 (d, J = 8,0 Hz, 1H, H3 de piridina), 3,48 (m, 1H), 3,24 (dd, J = 6,8, 10 Hz, 1H), 3,09-2,90 (m, 3H), 2,47 (m, 1H), 2,11 (m, 1H). GC-MS (El): 233 [m]+.
(C)
A seguir, o tetraidrotien-3-il-acetaldeído (1,10 g, 8,45 mmols) foi _ Γ;S=N-Oi (6)
A (1 E)-3-[6-(triflúor-metil)-piridin-3-il]-tetraidro-1 H-1 À4-tien-1 - ilidenocianamida (6) foi obtida a partir de 5-tetraidrotien-3-il-2-(triflúor-metil)- piridina como um pó esbranquiçado usando o mesmo procedimento descrito no Exemplo Ill (C) acima. O espectro de 1H RMN deste sólido apresentou ressonâncias para uma mistura 1:1 de diastereoisômeros. 1H RMN (acetona- d6) δ 8,85 (d, J = 2,2 Hz1 1H, H6 de piridina), 8,83 (d, J = 2,2Hz, 1H, H6 de piridina), 8,26 (dd, J = 2,2, 8,3 Hz, 1H, H4 de piridina), 8,15 (dd, J = 2,2, 8,3 Hz, 1H, H4 de piridina), 7,90 (d, J = 8,3 Hz, 1H, H3 de piridina), 7,86 (d, J = 8,3 Hz, 1 Η, H3 de piridina), 4,38 (dd, J = 8,7, 14 Hz, 1H), 4,23 (tt, J = 6, 12 Hz, 1H), 4,16 (ddd, J = 2,6, 8,3, 11,2 Hz, 1H), 3,83 (td, J = 8,7, 18 Hz, 1H), 3,68-3,48 (m, 3H), 3,29-3,17 (m, 2H), 2,95 (m, 1H), 2,85-2,79 (m, 3H), 2,33 (m,1 H). LC-MS (ELSD): 273 [m]+. Exemplo Vll
Preparação_de_f(5-flúor-6-cloro-piridin-3-il)-metin-(metil)-À4-
sulfanilidenocianamida (7)
(7)
(A)
(PHCO)1OjlNBS F^^V^Br
Ca4 Ci^N
Uma suspensão de 2-cloro-3-flúor-5-metil-piridina (5,1 g, 35 mmols), N-bromo-succinimida (6,1 g, 35 mmols) e peróxido de benzoíla (0,16 g, 0,66 mmol) em tetracloreto de carbono (100 mL) foi refluxada de um dia para o outro. Depois de resfriar, o sólido foi removido por filtração e o filtrado foi concentrado e carregado em uma coluna de sílica-gel eluída com 5% de EtOAc em hexano, para dar 3,77 g da 2-cloro-3-flúor-5-bromo-metil-
(D)
PhI(OAc)i
CHJCN
HJNCN pirídina desejada como um óleo incolor com 48% de rendimento. GC-MS
calculada para C6H4BrCIFN: 224,46. Encontrado: 224.
(B)
1V^Br
li J MeSW* , 'VV^
CJ^vN EiOH1R-T. Ci N
A 2-cloro-3-flúor-5-metil-tiometil-piridina foi obtida a partir de 2- cloro-3-flúor-5-bromo-metil-piridina usando o mesmo procedimento descrito no Exemplo Ill (B) acima. GC-MS calculada para C7H7CIFNS: 191,66. En- contrado: 191. (C)
Phl(OAc)1, NHjCN Cl^N THF, O0C CI-^N nCN
(7)
A [(5-flúor-6-cloro-piridin-3-il)-metil]-(metil)-À4-sulfanilidenociana- mida (7) foi obtida como um sólido esbranquiçado a partir de 2-cloro-3-flúor- 5-metil-tiometil-piridina usando o mesmo procedimento descrito no Exemplo Ill (C). LC-MS calculada para C8H7CIFN3S [M+1]+: 232,69. Encontrado: 232,04. Exemplo Vlll
Preparação_de_f(6-( 1.1 -diflúor-etil-piridin-3-in-metill-(metil)-X4-
sulfanilidenocianamida (8)
F F
(8)
Γ
n^-CN
(A)
^jQT νζΧ
11 r.L PP
F F
(A)
Adicionou-se trifluoreto de dietil-amino-sulfonila (DAST) (25,8 g, 260 mmols) a uma solução de 5-metil-2-acetil-piridina (9,9 g, 73,3 mmols) em CH2CI2 secado em peneiras moleculares (150 ml_) à temperatura ambi- ente, e a mistura foi agitada à temperatura ambiente durante a noite inteira. Mais DAST (12 g, 74 mmols) foi adicionado e a reação continuou por mais dois dias, após o que mais DAST (3,8 g, 23 mmols) foi adicionado e a rea- ção continuou por mais 3 dias. Depois de interromper a reação lentamente com solução saturada de NaHCO3 a 0 0C, a fase orgânica foi separada, se- cada com Na2SO4, filtrada, e concentrada. O resíduo foi purificado em sílica- gel eluída com 8% de EtOAc em hexano (v/v), para dar 3,91 g de 2-(1,1- diflúor-etil)-5-metil-piridina (A) como um óleo amarronzado com 34% de ren- dimento. GC-MS massa calculada para C8H9F2N [M]+: 157. Encontrado: 157.
mmols), N-bromo-succinimida (2,2 g, 12,7 mmols) e peróxido de benzoíla (0,15 g, 0,63 mmol) em tetracloreto de carbono (100 mL) foi refluxada duran- te a noite inteira. Depois de remover o sólido por filtração, o filtrado foi con- centrado. O resíduo foi redissolvido em etanol (40 mL) e adicionou-se tiome- tóxido de sódio (1,33 g, 19 mmols) à temperatura ambiente, e agitou-se por 3 h. O solvente foi removido sob pressão reduzida e a mistura remanescente foi dissolvida em CH2CI2 e água. Depois da separação, a camada orgânica foi secada com Na2SO4, filtrada e concentrada. O produto bruto 2-(1,1- diflúor-etil)-5-metil-tiometil-piridina (B) era 94% puro em GC-MS e foi usado diretamente na próxima reação sem purificação adicional. GC-MS: massa calculada para C9H11F2NS [M]+: 203. Encontrado: 203.
(B)
F
(B)
Uma mistura de 2-(1,1-diflúor-etil)-5-metil-piridina (A) (2,0 g, 12,7
(A)
(C)
(B)
(8)
25
A [(6-(1,1 -diflúor-etil-piridin-3-il)-metil]-(metil)-X4-sulfanilidenocia- namida (8) foi obtida a partir de 2-(1,1-diflúor-etil)-5-metil-tiometil-piridina (B) como um sólido amarronzado, usando o mesmo procedimento descrito no Exemplo Ill (C). LC-MS: massa calculada para Ci0H11F2N3S [M]+: 243,28. Encontrado: [M+1 ]+ 244,11. Exemplo IX
Preparação de cis-f2-(6-cloro-piridin-3-il)-ciclo-pentin-(metil)-À4- sulfanilidenocianamida (9)
etóxi-etano (100 mL) em um frasco de 250 mL com fundo redondo secado em estufa e purgado com nitrogênio, em um banho de gelo seco/acetona sob nitrogênio. Adicionou-se n-BuLi (1,05 g, 16,4 mmols, 6,6 mL de uma so- lução 2,5 M em hexanos) por intermédio de uma seringa, e a mistura laranja homogênea foi deixada agitando por 1 hora. Adicionou-se ciclo-pentanona (1,3 g, 15,6 mmols) por intermédio de uma seringa, e a mistura foi deixada aquecer até -20 0C antes de ser arrefecida com HCI 1 Ν. A mistura foi extra- ída com EtOAc e o extrato orgânico foi lavado com solução saturada de NaHCO3. O água da lavagem com NaHCO3 foi usada para neutralizar a pri- meira camada aquosa, e as camadas aquosas combinadas foram extraídas com mais EtOAc, e as camadas orgânicas combinadas foram secadas (Na2S04), filtradas, concentradas, e purificadas por cromatografia instantâ- nea em sílica-gel (hexanos.EtOAc 2:1), para dar 1-(6-cloro-piridin-3-il)-ciclo- pentanol (2,33 g, 76%) como um sólido esbranquiçado: p.f. 92-93 0C. LC-MS (ESI) m/z 197. 1H RMN (300 MHz, CDCI3) δ 8,50 (d, 1H, J = 2,4 Hz), 7,77 (dd, 1H, J = 8,4, 2,4 Hz), 7,28 (d, 1H, J = 8,4 Hz), 2,05-1,80 (m, 8H), 1,60 (s,
(A)
5-Bromo-2-cloro-piridina (3,0 g, 15,6 mmols) foi dissolvida em 1Η, OH). (B)
α
Cl η
0 1-(6-cloro-piridin-3-il)-ciclo-pentanol (2,1 g, 10,5 mmols) foi tratado com ácido acético (12 mL) e ácido sulfúrico (4 mL), e a mistura foi aquecida sob refluxo por 30 min. Depois de resfriar até a temperatura ambi- ente, gelo e NaOH 2 N (180 mL) foram adicionados e o precipitado bronzea- do resultante foi coletado por filtração, lavada com H2O e secado, dando 2- cloro-5-(ciclo-pent-1-enil)-piridina (1,66 g, 88%) como um sólido bronzeado: p.f. 59-60°C, LC-MS (ESI) m/z 179, 1H RMN (300 MHz, CDCI3) δ 8,41 (d, 1H, D J = 2,4 Hz), 7,66 (dd, 1H, J = 8,4, 2,4 Hz), 7,25 (d, 1H, J = 8,4 Hz), 6,27 (t, 1H, J = 2,1 Hz), 2,69 (bm, 2H), 2,55 (bm, 2H), 2,05 (m, 2H).
vida em THF (30 mL) em um frasco de 250 mL com fundo redondo secado em estufa e purgado com nitrogênio, e a solução resultante foi resfriada em um banho de gelo seco/acetona sob nitrogênio. Adicionou-se o complexo de BH3/THF (2,4 g, 28,0 mmols, 28 mL de uma solução 1 M em THF) sob a for- ma de gotas e agitação por intermédio de uma seringa, e a mistura foi dei- xada aquecer lentamente até a temperatura ambiente e agitada durante a noite inteira. NaOH 2 N (15 mL), etanol (15 mL) e H2O2 a 35% (10 mL) foram adicionados e a mistura foi agirtada por 0,5 h e depois diluída com EtOAc e HCI 1 N. As camadas foram separadas e a camada orgânica foi lavada com salmoura e solução aquosa de NaHSO3, secada com Na2SO4, filtrada atra- vés de Celite, e concentrada. A purificação por cromatografia instantânea (hexanos:EtOAc 10:1 -> 2:1) deu na ordem de eluição os subprodutos 2- cloro-5-ciclo-pentil-piridina (0,45 g, 29%) e 1-(6-cloro-piridin-3-il)-ciclo-
(C)
2-cloro-5-(ciclo-pent-1-enil)-piridina (1,5 g, 8,5 mmols) foi dissol- pentanol (0,44 g,26%), e em seguida, o produto desejado trans-2-(6-cloro- piridin-3-il)-ciclo-pentanol (0,25 g, 15%) como um óleo límpido: LC/MS (ESI) m/z 197, 1H RMN (300 MHz, CDCI3) δ 8,26 (d, 1H, J = 2,4 Hz), 7,55 (dd, 1H, J = 8,4, 2,4 Hz), 7,25 (d, 1H, J = 8,4 Hz), 4,12 (m, 1H), 2,88 (m, 1H), 2,24- 1,62 (m,6H). (D)
O trans-2-(6-cloro-piridin-3-il)-ciclo-pentanol (0,225 g, 1,14 mmol) foi dissolvido em CH2CI2 (10 mL) em um frasco de 50 mL com fundo redon- do, a solução foi resfriada em um banho de gelo sob nitrogênio e tratada com Et3N (0,172 g, 1,71 mmol, 0,24 mL) e cloreto de metanossulfonila (0,163 g, 1,42 mmol, 0,11 mL) por intermédio de uma seringa sob agitação. Depois de 1 j, a TLC (hexanos:EtOAc 2:1) indicou conversão completa. A mistura reativa foi concentrada sob vácuo e depois fracionada entre EtOAc eHCI 1 N. As camadas foram separadas e as frações orgânicas foram seca- das (Na2SO4), filtradas e concentradas, para dar o éster de 2-(6-cloro-piridin- 3-il)-ciclo-pentila do ácido trans-metanossulfônico (0,303 g, 97%) como um óleo: LC/MS (ESI) m/z 275, 1H RMN (300 MHz, CDCI3) δ 8,28 (d, 1H, J = 2,7 Hz), 7,56 (dd, 1H, J = 8,1, 2,7 Hz), 7,3 (d, 1H, J = 8,1 Hz), 4,93 (q aparente, 1H, J = 5,7 Hz), 3,28 (q aparente, 1H, J = 8,7 Hz), 2,86 (m, 2H), 2,10-1,80 (m, 3H), 1,73 (m, 1H). (E)
O éster de 2-(6-cloro-piridin-3-il)-ciclo-pentila do ácido trans- metanossulfônico (0,295 g, 1,07 mmol) foi dissolvido em EtOH (5 mL) em um frasco de 25 mL com fundo redondo e resfriado em um banho de gelo sob nitrogênio. Adicionou-se metano-tiolato de sódio (0,224 g, 3,20 mmols) de uma só vez e a mistura branca turva foi deixada aquecer até a temperatura ambiente e agitando de um dia para o outro. A mistura foi diluída com EtOAc e salmoura, e as camadas foram separadas. A camada orgânica foi lavada com salmoura, secada (Na2SO4), filtrada, e concentrada. A purificação por cromatografia instantânea e, sílica-gel (hexanos:EtOAc 10:1) deu cis-2-cloro- 5-(2-metil-tio-ciclo-pentil)-piridina (0,148 g, 61 %) como um óleo: LC/MS (ESI) m/z 227, 1H RMN (300 MHz, CDCI3) δ 8,27 (d, 1H, J = 2,7 Hz), 7,60 (dd, 1H, J = 8,1, 2,7 Hz), 7,26 (d, 1H, J = 8,1 Hz), 3,30 (m, 2H), 2,24 (m, 1H), 2,15- 1,65 (m, 5H), 1,74 (s, 3H).
sulfanilidenocianamida (9) foi otida como uma mistura oleosa 1:1 de diaste- reoisômeros a partir de cis-2-cloro-5-(2-metil-tio-ciclo-pentil)-piridina, usando o mesmo procedimento descrito no Exemplo Ill (C). LC/MS (ESI) m/z 267, 1H RMN (300 MHz, CDCI3) δ 8,31 (d, 2H, J = 2,7 Hz), 7,70 (dd, 1H, J = 8,4, 2,7 Hz), 7,63 (dd, 1H, J = 8,4, 2,7 Hz), 7,40 (d, 1H, J = 8,4 Hz), 7,32 (d, 1H, J = 8,4 Hz), 3,96 (m, 1H), 3,81 (m, 1H), 3,67-3,51 (m, 2H), 2,73 (s, 3H), 2,59 (m, 1H), 2,45 (s, 3H), 2,40-1,95 (m, 9H), 1,85 (m, 2H). Exemplo X
Preparação_de_f(4.6-dicloro-piridin-3-il)-metill-(metil)-À4-
sulfanilidenocianamida (10)
(F)
10
A
cis-[2-(6-cloro-piridin-3-il)-ciclo-pentil]-(metil)-À4-
(10)
CN
(A)
CO1Bt , UAlH4
THF α Π
OH
Cr N
Adicionou-se uma solução 1 M de LiAIH4 em THF (25 mL, 25 mmols) na forma de gotas a uma solução de 4,6-dicloro-nicotinato de etila (8,8 g, 40 mmols) em THF anidro (75 mL) sob agitação e resfriada em um banho de gelo. Durante a adição, a temperatura não foi deixada ultrapassar 0C. Depois de terminada a adição, a reação foi aquecida até 40 0C por 15 min, resfriada, e depois interrompida pela adição sucessiva de água, solução aquosa a 15% de NaOH (0,95 mL) e água (1,85 mL) na forma de gotas (0,95 mL). A mistura foi filtrada através de Celite e o filtrado foi secado (MgSO4)1 passado através de um leito curto de sílica-gel e concentrado para dar um óleo vermelho. Adicionou-se éter (100 mL) após o que apareceu imediata- mente um precipitado gomoso que foi removido por filtração. A solução eté- rea foi deixada descansando à temperatura ambiente durante a noite inteira, e durante este tempo mais precipitado se formou que foi removido novamen- te por filtração. A solução etérea foiconcentrada e secada para dar 3,25 g do produto 2,4-dicloro-5-hidróxi-metil-piridina com 46% de rendimento como um sólido oleoso quase incolor. 1H RMN (300 MHz, CDCI3) δ 8,5 (s, 1H), 7,4 (s, 1H), 4,8 (s, 2H), 2,7 (bs, 1H); GC-MS: massa calculada para C6H5CI2NO [M]+, 177. Encontrado 177.
18 mmols) foi convertido em 2,0 g de 2,4-dicloro-5-cloro-metil-piridina (57% de rendimento) como um óleo amarelo usando o mesmo procedimento des- crito no Exemplo Il (D). 1H RMN (300 MHz, CDCI3) δ 8,4 (s, 1H), 7,4 (s, 1H), 4,7 (s, 2H); GC-MS: massa calculada para C6H4CI3N [M]+, 195. Encontrado 195.
(B)
O material de partida 2,4-dicloro-5-hidróxi-metil-piridina (3,2 g,
(C)
TKF
A 2,4-dicloro-5-metil-tiometil-piridina (2,0 g, 94% de rendimento) foi preparada como um óleo amarelo a partir de 2,4-dicloro-5-cloro-metil- piridina (2,0 g, 1,0 mmol) usando o mesmo método descrito no Exemplo I, procedimento (A). 1H RMN (300 MHz, CDCI3) δ 8,3 (s, 1H), 7,4 (s, 1H), 3,7 (s, 2H), 2,0 (s, 3H); GC-MS: massa calculada para C7H7CI2NS [M]+, 207. En- contrado 207. (D)
JLx-V5^ HaNCN1Fhi(OAc)j ÍtY
Cl-^N CH3OltO-C Cl-^N NCN
(10)
A [(4,6-dicloro-piridin-3-il)-metil]-(metil)-À4-sulfanilidenocianamida (10) foi preparada como uma goma amarelo-pálida a partir de 2,4-dicloro-5- metil-tiometil-piridina usando o mesmo método descrito no Exemplo I (B). 1H RMN (400 MHz, DMSO) δ 8,48 (s, 1H), 7,93 (s, 1H), 4,68 (d, 1H), 4,49 (d, 1H), 2,95 (s, 3H); LC-MS (ELSD): massa calculada para C8H7CI2N3S [M]+, 248. Encontrado 248. Exemplo Xl Testes Inseticidas
Os compostos identificados nos exemplos precedentes foram
testados contra afidídeo do algodão e afidídeo do pêssego-verde, usando os procedimentos aqui descritos abaixo.
Teste Inseticida para Afidídeo do Algodão (Aphis aossvDii) em Ensaio de Sprav Foliar
As abóboras com folhas de cotilédones completamente expandi-
dos foram podadas até um cotilédone por planta e infestadas com afidídeo de algodão (adulto áptero e ninfa) 1 dia antes da aplicação química. Cada planta foi examinada antes da aplicação química para assegurar infestação apropriada (cerca de 30-70 afidídeos por planta). Os compostos (2 mg) fo-
ram dissolvidos em 2 mL da mistura de solventes acetona:metanol (1:1), formando soluções de insumo de 1.000 ppm. As soluções de insumo foram diluídas 5X com Tween 20 a 0,025% em H2O para obter uma solução a 200 ppm. Concentrações mais baixas (50, 12,5 e 3,13 ppm) foram preparadas fazendo diluições seqüenciais de 4X a partir da solução a 200 ppm com um diluente que consiste em 80 partes de Tween 20 a 0,025% em H2O e 20 par- tes de acetona:metanol (1:1). Um borrifador manual Devilbiss foi usado para aplicar as soluções de aspersão até escorrer por ambos lados das folhas de cotilédone da abóbora. Quatro plantas (4 replicações) foram usadas para cada concentração de cada composto. As plantas referenciais (controle com solvente) foram borrifadas apenas com o diluente. As plantas tratadas foram mantidas em uma sala de contenção por 3 dias a aproximadamente 23 0C e 40% de umidade relativa, antes de o número de afidídeos vivos em cada planta ser registrado. A atividade inseticida foi medida por Controle Percen- tual (%) Corrigido, usando a fórmula de correção de Abbott e está apresen- tada na Tabela 1:
Controle % Corrigido = 100 * (X - Υ) / X onde X = Ne de afidídeos vivos nas plantas de controle com solvente Y = Nq de afidídeos vivos em plantas tratadas Teste Inseticida para Afidídeo do Pêssego Verde (Myzus persicae) em En- saio de Sprav Foliar
Mudas de repolho desenvolvidas em vasos de 7,5 cm (3 in), com 2-3 pequenas (3-5 cm) folhas verdadeiras, foram usadas como substrato do teste. As mudas foram infestadas com 20-50 afidídeos de pêssego verde (adulto áptero e ninfa) 2-3 dias antes da aplicação química. Quatro mudas foram usadas para cada tratamento. Os compostos (2 mg) foram dissolvidos em 2 mL da mistura de solventes acetona:metanol (1:1), formando soluções de insumo de 1.000 ppm. As soluções de insumo foram diluídas 5X com Tween 20 a 0,025% em H2O para obter uma solução a 200 ppm. Concentra- ções mais baixas (50, 12,5 e 3,13 ppm) foram preparadas fazendo diluições seqüenciais de 4X a partir da solução a 200 ppm com um diluente que con- siste em 80 partes de Tween 20 a 0,025% em H2O e 20 partes de aceto- na:metanol (1:1). Um borrifador manual Devilbiss foi usado para borrifar uma solução sobre ambos lados das folhas de repolho até escorrer. As plantas referenciais (controle com solvente) foram borrifadas apenas com o diluente. As plantas tratadas foram mantidas em uma sala de contenção por 3 dias a aproximadamente 23 0C e 40% de umidade relativa, antes da classificação. A avaliação foi conduzida contando o número de afidídeos vivos por planta sob um micriscópio. A atividade inseticida foi medida usando a fórmula de correção de Abbott:
Controle % Corrigido = 100 * (X - Υ) / X onde X = N2 de afidídeos vivos nas plantas de controle com solvente Y = N2 de afidídeos vivos em plantas tratadas
Os valores do Controle Percentual Corrigido dos ensaios estão
indicados na Tabela 1. Tabela 1
Comp. N2 CA 200 CA 50 GPA 200 GPA 50 1 A D G G 2 A A A A 3 A A A A 4 A C F G A E G G 6 A A C E 7 A A C D 8 A A A D 9 D G D G B G G G
CA 200 refere-se a % de controle a 200 ppm contra afidídeo do
algodão em testes de spray foliar
CA 50 refere-se a % de controle a 50 ppm contra afidídeo do algodão em testes de spray foliar
GPA 200 refere-se a % de controle a 200 ppm contra afidídeo do pêssego verde em testes de spray foliar
GPA 50 refere-se a % de controle a 50 ppm contra afidídeo do pêssego verde em testes de spray foliar
Em cada caso da Tabela 1, a escala de pontuação é a seguinte: % de Controle (ou Mortalidade) Pontuação 90-100 A 80-89 B 70-79 C 60-69 D 50-59 E Menos do que 50 F Inativo G Não testado H
Utilidade dos Inseticidas
Os compostos da invenção são úteis para o controle de inverte- brados, incluindo insetos. Portanto, a presente invenção refere-se também a um método para inibir um inseto, compreendendo aplicar uma quantidade inibidora de inseto de um composto da fórmula (I) a um local do inseto, à área a ser protegida, ou diretamente sobre o inseto a ser controlado. Os compostos da invenção podem ser usados também para controlar outras pragas de invertebrados, tais como ácaros e nematódeos.
O "local" de insetos ou outras pragas é um termo aqui utilizado para se referir ao ambiente no qual os insetos ou outras pragas vivem ou onde seus ovos estão presentes, incluindo o ar que os circunda, o alimento que eles comem, ou os objetos com os quais eles entram em contato. Por exemplo, os insetos que comem, danificam ou contatam plantas comestí- veis, comercializáveis, ornamentais, turfosas ou de pasto, podem ser contro- lados aplicando os compostos ativos à semente da planta antes de plantar, à muda, ou broto que é plantado, às folhas, pedúnculos, frutos, grãos e/ou raí- zes, ou ao solo ou outro meio de crescimento, antes que a cultura seja plan- tada. A proteção destas plantas contra doenças virais, fúngicas ou bacteria- nas pode ser conseguida também indiretamente através do controle das pragas que se alimentam de seiva tais como mosca-branca, gafanhoto das plantas, afidídeo e ácaro-aranha. Tais plantas incluem aquelas que são ali- mentadas através de abordagens convencionais e que são geneticamente modificadas usando biotecnologia moderna para ganhar traços de resistên- cia a insetos, resistência a herbicidas, intensificação de nutrição, e/ou quais- quer outros traços benéficos.
Contempla-se que os compostos poderiam ser úteis também para proteger produtos têxteis, papel, grãos armazenados, sementes e ou- tros produtos alimentícios, residências e outros prédios que podem ser ocu- pados por seres humanos e/ou animais de companhia, fazenda, rancho, zoológico, ou outros animais, aplicando um composto ativo a esses objetos ou perto deles. Os animais domesticados, prédios ou seres humanos pode- riam ser protegidos com os compostos controlando pragas de invertebrados e/ou nematódeos que são parasitários ou são capazes de transmitir doenças infecciosas. Essas pragas incluem, por exemplo, bichos-de-pé, carrapatos, piolhos, mosquitos, moscas, pulgas e dirofilárias. As aplicações não- agronômiccas incluem também controle de pragas de invertebrados em flo- restas, quintais, ao longo de acostamentos de estradas, e direitos de passa- gem em ferrovias.
O termo "inibir um inseto" refere-se a uma diminuição nos núme- ros de insetos vivos, ou um decréscimo no número de ovos de insetos viá- veis. O grau de redução realizado por um composto depende, evidentemen- te, da taxa de aplicação do composto, do composto específico usado, e da espécie do inseto-alvo. Pelo menos uma quantidade inativadora deveria ser usada. O termo "quantidade inativadora de inseto" é utilizado para descrever a quantidade que é suficiente para causar uma redução mensurável na po- pulação de insetos tratada. Geralmente, uma quantidade na faixa entre cer- ca de 1 e cerca de 1.000 ppm em peso de composto ativo é usada. Por e- xemplo, os insetos ou outras pragas que podem ser inibidas incluem, porém sem limitações:
Lepidópteros - Heliothis spp., HeHcoverpa spp., Spodoptera spp., Mythimna unipuncta, Agrotis ipsilon, Earias spp., Euxoa auxiiiaris, Tri- choplusia ni, Anticarsia gemmatalis, Rachipiusia nu, PiuteIIa xylostella, Chilo spp., Seirpophaga ineertulas, Sesamia inferens, Cnaphaloeroeis medinalis, Ostrinia nubilalis, Cydia pomonella, Carposina niponensis, Adoxophyes ora- na, Arehips argyrospiius, Pandemis heparana, Epinotia aporema, Eupoecilia ambiguella, Lobesia botrana, Polychrosis viteana, Pectinophora gossypiella, Pieris rapae, Phyllonoryeter spp., Leucoptera malifoliella, Phyllocnisitis eitrel- Ia
Coleópteros - Diabrotiea spp., Leptinotarsa deeemlineata, Ou- lema oryzae, Anthonomus grandis, Lissorhoptrus oryzophilus, Agriotes spp., Melanotus eommunis, PopiHia japoniea, Cyclocephala spp., Tribolium spp.
Homópteros - Aphis spp., Myzus persieae, Rhopalosiphum spp., Dysaphis plantaginea, Toxoptera spp., Maerosiphum euphorbiae, Aulaeor- thum solani, Sitobion avenae, Metopolophium dirhodum, Sehizaphis grami- ) num, Brachycolus noxius, Nephotettix spp., Nilaparvata lugens, Sogatella fureifera, Laodelphax striatellus, Bemisia tabaei, Trialeurodes vaporariorum, Aleurodes proletella, Aleurothrixus floeeosus, Quadraspidiotus pernieiosus, Unaspis yanonensis, Ceroplastes rubens, Aonidieila aurantii
Hemípteros - Lygus spp., Eurygaster maura, Nezara viridula, Piezodorus guildingi, Leptoeorisa varieornis, Cimex leetularius, Cimex hemip- terus
Tisanópteros - Frankliniella spp., Thrips spp., Seirtothrips dorsa-
Iis
Isópteros - Retieuiitermes flavipes, Coptotermes formosanus, Reticulitermes virginieus, Heterotermes aureus, Retieulitermes hesperus, Coptotermes frenehii, Shedorhinotermes spp., Retieulitermes santonensis, Retieulitermes grassei, Retieulitermes banyulensis, Retieulitermes speratus, Retieulitermes hageni, Reticulitermes tibialis, Zootermopsis spp., Ineisitermes spp., Marginitermes spp., Maerotermes spp., Microeerotermes spp., Miero- termes spp.
Dípteros - Liriomyza spp., Musea domestica, Aedes spp., Culex spp., Anophelesspp., Fannia spp., Stomoxys spp.,
Himenópteros - Iridomyrmex humilis, Solenopsis spp., Monomo- rium pharaonis, Atta spp., Pogonomyrmex spp., Camponotus spp., Monomo- rium spp., Tapinoma sessile, Tetramorium spp., Xyloeapa spp., Vespula spp., Polistes spp.
Mallophaga (piolho mastigador) Anopluros (piolho sugador) - Pthirus púbis, Pediculus spp.
Ortópteros (gafanhotos, grilos) - Melanoplus spp., Locusta migra- tória, Schistocerca gregaria, Gryllotalpidae (grilo-toupeira).
Blatídeos (baratas) - Blatta orientalis, Blattella germanica, Peri- planeta americana, Supella longipalpa, Periplaneta australasiae, Periplaneta brunnea, Pareoblatta pennsylvaniea, Periplaneta fuliginosa, Pyenoseelus su- rinamensis,
Sifonápteros - Ctenophalidesspp., Pulexirritans
Ácaros - Tetranyehus spp., Panonyehus spp., Eotetranychus earpini, Phyllocoptruta oleivora, Aculus pelekassi, Brevipalpus phoenieis, Bo- ophilus spp., Dermaeentor variabilis, Rhipicephalus sanguineus, Amblyomma amerieanum, Ixodes spp., Notoedres eati, Sareoptes seabiei, Dermatopha- goides spp.
Nematódeos - Dirofilaria immitis, Meloidogyne spp., Heterodera spp., Hoplolaimus eolumbus, Belonolaimus spp., Pratylenehus spp., Rotylen- ehus reniformis, Crieonemella ornata, Ditylenehus spp., Aphelenehoides bes- seyi, Hirsehmanniella spp. Composições
Os compostos desta invenção são aplicados na forma de com- posições que são modalidades importantes da invenção, e que compreen- dem um composto desta invenção e um veículo inerte fitologicamente acei- tável. O controle das pragas é conseguido aplicando os compostos da in- venção nas formas de sprays, tratamento tópico, géis, revestimentos de se- mentes, microencapsulamentos, absorção sistêmica, iscas, massas, pulveri- zadores, fumigadores, aerossóis, pós e muitos outros. As composições são formulações sólidas ou líquidas concentradas que são dispersadas em água para aplicação, ou são formulações em pó ou granulares que são aplicadas sem tratamento adicional. As composições são preparadas de acordo com procedimentos e fórmulas convencionais nas técnicas de química agrícola, mas que são inusitados e importantes por causa da presença dos compos- tos desta invenção. Alguma descrição da formulação das composições sera fornecida, entretanto, para assegurar que os químicos agrícolas possam preparar facilmente qualquer composição desejada.
As dispersões nas quais os compostos são aplicados são mais freqüentemente suspensões ou emulsões aquosas preparadas a partir de formulações concentradas dos compostos. Essas formulações solúveis em água, que podem ser colocadas em suspensão ou emulsificadas em água, são sólidas, usualmente conhecidas como pós umectáveis, ou líquidas usu- almente conhecidas como concentrados emulsificáveis ou suspensões a- quosas. Os pós umectáveis, que podem ser compactados para formar grâ- nulos dispersáveis em água, compreendem uma mistura íntima do composto ativo, um veículo inerte, e tensoativos. A concentração do composto ativo é usualmente entre cerca de 10% e cerca de 90% em peso. O veículo inerte é usualmente escolhido entre argilas atapulgita, argilas montmorilonita, terras diatomáceas, ou silicatos purificados. Os tensoativos eficazes, que compre- endem entre cerca de 0,5% e cerca de 10% do pó umectável, são encontra- dos entre as Iigninas sulfonadas, os naftalenossulfonatos condensados, os naftalenossulfonatos, os alquil-benzenossulfonatos, os sulfatos de alquilas, e tensoativos não-iônicos tais como adutos óxido de etileno com alquil-fenóis.
Os concentrados emulsificáveis dos compostos compreendem uma concentração conveniente de um composto, tal como entre cerca de 50 e cerca de 500 gramas por litro de líquido, equivalente a cerca de 10% a cerca de 50%, dissolvido em um veículo inerte que é um solvente miscível em água ou uma mistura de solvente orgânico imiscível em água e emulsifi- cantes. Os solventes orgânicos úteis incluem solventes aromáticos, especi- almente os xilenos, e as frações de petróleo, especialmente as partes nafta- lênicas e olefínicas de alto ponto de ebulição do petróleo, tal como nafta a- romática pesada. Outros solventes orgânicos também podem ser usados, tais como solventes terpênicos incluindo derivados de breu, cetonas alifáti- cas tais como ciclo-hexanona, e álcoois complexos tais como 2-etóxi-etanol. Os emulsificantes apropriados para os concentrados emulsificáveis são es- colhidos entre tensoativos aniônicos e/ou não-iônicos convencionais, tais como aqueles discutidos acima.
As suspensões aquosas compreendem suspensões de compos- tos insolúveis em água desta invenção, dispersados em um veículo aquoso em uma concentração na faixa entre cerca de 5% e cerca de 50% em peso. As suspensões são preparadas moendo finamente o composto, e misturan- do-o intensamente dentro de um veículo que compreende água e tensoati- vos escolhidos entre os mesmos tipos discutidos acima. Ingredientes inertes, tais como sais inorgânicos e gomas sintéticas ou naturais, também podem ser adicionados, para aumentar a densidade e a viscosidade do veículo a- quoso. É freqüentemente mais eficaz moer e misturar o composto na mesma hora, preparando a mistura aquosa, e homogeneizando-a em um equipa- mento tal como um moinho de areia, moinho de esferas, ou homogeneizador do tipo êmbolo.
Os compostos podem ser aplicados também como composições granulares, que são particularmente úteis para aplicações ao solo. As com- posições granulares contêm usualmente entre cerca de 0,5% e cerca de 10% em peso do composto, dispersado em um veículo inerte que consiste inteiramente ou em grande parte em argila ou uma substância barata similar. Tais composições são preparadas usualmente dissolvendo o composto em um solvente apropriado e aplicando-o a um veículo granular que foi pré- formado até o tamanho de partícula apropriado, na faixa entre cerca de 0,5 e 3 mm. Tais composições podem ser formuladas também fazendo uma mas- sa ou pasta do veículo e composto e esmagando e secando, para obter o tamanho de partícula granular desejado.
Os pós que contêm os compostos são preparados simplesmente misturando intimamente o composto na forma de pó com um veículo agrícola pulverulento, tal como argila caulim, rocha vulcânica triturada, e similares. Os pós podem conter adequadamente entre cerca de 1% e cerca de 10% do composto.
É igualmente prático, quando desejável por qualquer razão, apli- car o composto na forma de uma solução em um solvente orgânico apropri- ado, usualmente um óleo de petróleo brando, tais como óleos de spray, que são amplamente utilizados em química agrícola.
Os inseticidas e acaricidas são aplicados geralmente na forma de uma dispersão do ingrediente ativo em um veículo líquido. É convencio- nal referir-se às taxas de aplicação em termos da concentração do ingredi- ente ativo no veículo. O veículo mais amplamente usado é a água.
Os compostos da invenção podem ser aplicados também na forma de uma composição de aerossol. Em tais composições o composto ativo é dissolvido ou dispersado em um veículo inerte, que é uma mistura de propelentes geradores de pressão. A composição de aerosol é embalada em um recipiente a partir do qual a mistura é distribuída através de uma válvula atomizadora. As misturas de propelentes compreendem hidrocarbonetos halogenados de baixo ponto de ebulição, que podem ser misturados com solventes orgânicos, ou suspensões aquosas pressurizadas com gases iner- tes ou hidrocarbonetos gasosos.
A quantidade real de composto a ser aplicada aos locais de inse- tos e ácaros não é crítica e pode ser determinada facilmente pelos versados nessas técnicas, levando em consideração os exemplos acima. Geralmente, espera-se que concentrações entre 10 ppm e 5.000 ppm em peso do com- posto proporcionem bom controle. Com muitos dos compostos, concentra- ções entre 100 e 1.500 ppm serão suficientes.
O local ao qual um composto é aplicado pode ser qualquer local inabitado por um inseto ou ácaro, por exemplo, culturas de vegetais, árvores frutíferas e de nozes, videiras de uvas, plantas ornamentais, animais domes- ticados, superfícies internas ou externas de prédios, e o solo ao redor dos prédios.
Por causa da capacidade singular de os ovos de insetos resisti- rem à ação intoxicante, aplicações repetidas podem ser desejáveis para con- trolar larvas recém-emergidas, como é verdadeiro no caso de outros insetici- das e acaricidas conhecidos.
A movimentação sistêmica dos compostos da invenção em plan- tas pode ser utilizada para controlar pragas em uma parte da planta, apli- cando os compostos a uma parte diferente dela. Por exemplo, o controle de insetos de alimentação foliar pode ser feito por irrigação de gotejamento ou aplicação em leiras, ou tratando a semente antes de plantar. Esse tratamen- to pode ser aplicado a todos os tipos de sementes, incluindo aquelas a partir das quais as plantas geneticamente transformadas que expressam traços especializados germinarão. Os exemplos representativos incluem aquelas que expressam proteínas tóxicas para pragas de invertebrados, tais como Bacillus thuringiensis ou outras proteínas inseticidas, aquelas que expres- sam resistência a herbicidas, tais como a semente "Roundup Ready®", ou aquelas com genes estranhos "empilhados" que expressam porteínas inseti- cidas, resistência a herbicidas, intensificação de nutrição e/ou quaisquer ou- tros traços benéficos. Uma composição de isca inseticida que consiste em compostos
da presente invenção e atrativos e/ou estimulantes de alimentação pode ser usada para aumentar a eficácia dos inseticidas contra pragas de insetos em um dispositivo tal como uma armadilha, estação de isca, e similares. A com- posição de isca é usualmente uma matriz de isca sólida, semi-sólida (inclu- indo gel) ou líquida que inclui os estimulantes e um ou mais inseticidas não- microencapsulados ou microencapsulados em uma quantidade eficaz para atuar como agentes exterminadores.
Os compostos da presente invenção (Fórmula I) são freqüente- mente aplicados em conjunto com um ou mais outros inseticidas ou fungici- das ou herbicidas para obter controle de uma série mais ampla de doenças de pragas e ervas daninhas. Quando usados em conjunto com outros inseti- cidas ou fungicidas ou herbicidas, os compostos presentemente reivindica- dos podem ser formulados com os outros inseticidas ou fungicidas ou herbi- cidas, misturados em tanque com os outros inseticidas ou fungicidas ou her- bicidas, ou aplicados seqüencialmente com os outros inseticidas ou fungici- das ou herbicidas.
Alguns dos inseticidas que podem ser empregados de forma be- néfica em combinação com os compostos da presente invenção incluem: "inseticidas antibióticos", tais como alosamidina e turingiensina; "inseticidas de Iactonas macrocíclicas", tais como espinosad, espinetoram, e outras es- pinosinas incluindo as 21-butenil-espinosinas e seus derivados; "inseticidas avermactinas" tais como abamectina, doramectina, emamectina, eprinomec- tina, ivermectina e selamectina; "inseticidas milbemicinas" tais como Iepi- mectina, milbemectina, milbemicina oxima e moxidectina; "inseticidas arsê- nicos" tais como arseniato de cálcio, acetoarsenito de cobre, arseniato de cobre, arseniato de chumbo, arsenito de potássio e arsenito de sódio; "inse- ticidas biológicos" tais como Bacillus popilliae, B. sphaericus, B. thuringiensis subsp. aizawai, B. thuringiensis subsp. kurstaki, B. thuringiensis subsp. te- nebrionis, Beauveria bassiana, vírus de granulose Cydia pomonella, NPV da mariposa-do-álamo de Douglas, NPV da mariposa-cigana, NPV de Helico- verpa zea, vírus da granulose da traça-indiana-da-farinha (Indian meai mo- th), Metarhizium anisopliae, Nosema Iocustae, Paecilomyees fumosoroseus, P. lilaeinus, Photorhabdus lumineseens, NPV de Spodoptera exigua, fator oostástico modulador de tripsina, Xenorhabdus nematophilus, e X. bovienii, "inseticidas protetores incorporados nas plantas" tais como CryIAb, Cry 1 Ac, CrylF, Cry1A.105, Cry2Ab2, Cry3A, mir Cry3A, Cry3Bb1, Cry34, Cry35, e VIP3A; "inseticidas botânicos" tais como anabasina, azadiractina, d- limoneno, nicotina, piretrinas, cinerinas, cinerina I, cinerina II, jasmolina I, jasmolina II, piretrina I, piretrina II, quassia, rotenona, riania e sabadila; "inse- ticidas de carbamatos" tais como bendiocarb e carbaril; "inseticidas de metil- carbamato de benzofuranila" tais como benfuracarb, carbofurano, carbossul- fan, decarbofurano e furatiocarb; "inseticidas de dimetilcarbamato" tais como dimitan, dimetilan, hiquincarb e pirimicarb; "inseticidas de carbamato oxima" tais como alanicarb, aldicarb, aldoxicarb, butocarboxim, butoxicarboxim, me- tomil, nitrilacarb, oxamil, tazimcarb, tiocarboxima, tiodicarb e tiofanox; "inse- ticidas de metilcarbamato de fenila" tais como alixicarb, aminocarb, bufen- carb, butacarb, carbanolato, cloetocarb, dicresilz, dioxacarb, EMPC, etiofen- carb, fenetacarb, fenobucarb, isoprocarb, metiocarb, metolcarb, mexacarba- to, promacil, promecarb, propoxur, trimetacarb, XMC e xililcarb; "inseticidas de dinitrofenol" tais como dinex, dinoprop, dinosam e DNOC; "inseticidas de flúor" tais como hexaflúor-silicato de bário, criolita, fluoreto de sódio, hexa- flúor-silicato de sódio e sulfluramid; "inseticidas de formamidina" tais como amitraz, clordimeform, formetanato e formparanato; "inseticidas fumigantes" tais como acrilonitrila, dissulfeto de carbono, tetracloreto de carbono, cloro- fórmio, cloropicrina, para-dicloro-benzeno, 1,2-dicloro-propano, formiato de etila, dibrometo de etileno, dicloreto de etileno, oxido de etileno, cianeto de hidrogênio, iodo-metano, brometo de metila, metil-clorofórmio, cloreto de metileno, naftaleno, fosfina, fluoreto de sulfurila e tetracloro-etano; "insetici- das inorgânicos" tais como bórax, polissulfeto de cálcio, oleato de cobre, clo- reto mercuroso, tiocianato de potássio, e tiocianato de sódio; "inibidores da síntese de quitinas" tais como bistrifluron, buprofezin, clorfluazuron, ciroma- zina, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, no- valuron, noviflumuron, penfluron, teflubenzuron e triflumuron; "miméticos de hormônios juvenis" tais como epofenonano, fenoxicarb, hidropreno, quino- preno, metopreno, piriproxifeno e tripreno; "hormônios juvenis" tais como hormônio juvenil I, hormônio juvenil Il e hormônio juvenil III; "agonistas de hormônios da muda tais como cromafenozida, halofenozida, metoxifenozida e tebufenozida; "hormônios da muda" tais como α-ecdisona e ecdisterona;
"inibidores da muda" tais como diofenolano; "precocenos" tais como preco- ceno I, precoceno Il e precoceno III; "reguladores do crescimento de insetos não classificados" tais como diciclanil; "inseticidas análogos de nereistoxina" tais como bensultap, cartap, tiociclam e tiosultap; "inseticidas nicotinóides" tais como flonicamid; "inseticidas de nitroguanidina" tais como clotianidina, dinotefurano, imidacloprid e tiametoxam; "inseticidas de nitrometileno" tais como nitenpiram e nitiazina; "iseticidas de piridil-metil-amina" tais como ace- tamiprid, imidacloprid, nitenpiram e tiacloprid; "inseticidas organoclorados" tais como bromo-DDT, canfeclor, DDT, ρρ'-DDT, etil-DDD, HCH, gama-HCH, lindano, metoxiclor, pentaclorofenol e TDE; "inseticidas de ciclodienos" tais como aldrin, bromociclen, clorbiciclen, clordano, clordecona, dieldrin, dilor, endossulfan, endrin, HEOD, heptaclor, HHDN, isobenzan, isodrin, kelevan e mirex; "inseticidas de organofosfatos" tais como bromfenvinfos, clorfenvinfos, crotoxifos, diclorvos, dicrotofos, dimetilvinfos, fospirato, heptenofos, metocro- tofos, mevinfos, monocrotofos, naled, naftalofos, fosfamidon, propafos, TEPP e tetraclorvinfos; "inseticidas de organotiofosfatos" tais como dioxa- benzofos, fosmetilan e fentoato; "inseticidas de organotiofosfatos alifáticos" tais como acetion, amiton, cadusafos, cloretoxifos, clormefos, demefion, de- mefion-O, demefion-S, demeton, demeton-O, demeton-S, demeíon-metila, demeton-O-metila, demeton-S-metila, demeton-S-metilsulfon, dissulfoton, etion, etoprofos, IPSP, isotioato, malation, metacrifos, oxidemeton-metila, oxideprofos, oxidissulfoton, forato, sulfotep, terbufos e tiometon; "inseticidas de organotiofosfatos de amidas alifáticas" tais como amidition, ciantoato, di- metoato, etoato-metila, formotion, mecarbam, ometoato, protoato, sofamida e vamidotion; "inseticidas de organotiofosfatos oximas" tais como clorfoxim, foxim e foxim-metila; "inseticidas de organotiofosfatos heterocíclicos" tais como azametifos, coumafos, coumitoato, dioxation, endotion, menazon, mor- fotion, fosalona, piraclofos, piridafention e quinotion; "inseticidas de organoti- ofosfatos de benzotiopirano" tais como diticrofos e ticrofos; "inseticidas de organotiofosfatos de benzotriazina" tais como azinfos-etila e azinfos-metila; "inseticidas de organotiofosfatos de isoindol" tais como dialifos e fosmet; "in- seticidas de organotiofosfatos de isoxazol" tais como isoxatión e zolaprofos; "inseticidas de organotiofosfatos de pirazolopirimidinas" tais como clorprazo- fos e pirazofos; "inseticidas de organotiofosfatos de píridina" tais como clorpi- rifos e clorpirifos-metila; "inseticidas de organotiofosfatos de pirimidina" tais como butatiofos, diazinon, etrimfos, lirimfos, pirimifos-etila, pirimifos-metilz, primidofos, pirimitato e tebupirimfos; "inseticidas de organotiofosfatos de quinoxalina" tais como quinalfos e quinalfos-metila; "inseticidas de organotio- fosfatos de tiadiazol" tais como atidation, litidation, metidation e protidation; "inseticidas de organotiofosfatos de triazol" tais como isazofos e triazofos; "inseticidas de organotiofosfatos de fenila" tais como azotoato, bromofos, bromofos-etila, carbofenotion, clortiofos, cianofos, citioato, dicapton, diclofen- tion, etafos, famfur, fenclorfos, fenitrotion fensulfotion, fention, fention-etila, heterofos, jodfenfos, mesulfenfos, paration, paration-metila, fenkapton, fosni- clor, profenofos, protiofos, sulprofos, temefos, triclormetafos-3 e trifenofos; "inseticidas de fosfonatos" tais como butonato e triclorfon; "inseticidas de fosfonotioatos" tais como mecarfon; "inseticidas de etilfosfonotioato de fenila" tais como fonofos e tricloronat; "inseticidas de fenilfosfonotioato de fenila" tais como cianofenfos, EPN e leptofos; "inseticidas de fosforamidatos" tais como crufomato, fenamifos, fostietano, mefosfolan, fosfolan e pirimetafos; "inseticidas de fosforamidotioatos" tais como acetato, isocarbofos, isofenfos, metamidofos e propetamfos; "inseticidas de fosforodiamidas" tais como di- mefox, mazidox, mipafox e schradan; "inseticidas de oxadiazinas" tais como indoxacarb; "inseticidas de ftalimidas" tais como dialifos, fosmet e tetrame- trin; "inseticidas de pirazóis" tais como acetoprol, etiprol, fipronil, pirafluprol, piriprol, tebufenpirad, tolfenpirad e vaniliprol; "inseticidas de ésteres piretrói- des" tais como acrinatrin, aletrin, bioaletrin, bartrin, bifentrin, bioetanometrin, cicletrin, cicloprotrin, ciflutrin, beta-ciflutrin, cialotrin, gama-cialotrin, Iambda- cialotrin, cipermetrin, alfa-cipermetrin, beta-cipermetrin, teta-cipermetrin, ze- ta-cipermetrin, cifenotrin, deltametrin, dimeflutrin, dimetrin, empentrin, fenflu- trin, fenpiritrin, fenpropatrin, fenvalerato, esfenvalerato, flucitrinato, fluvalina- to, tau-fluvalinato, furetrin, imiprotrin, metoflutrin, permetrin, biopermetrin, transpermetrin, fenotrin, praletrin, proflutrin, piresmetrin, resmetrin, biorres- metrin, cismetrin, teflutrin, teraletrin, tetrametrin, tralometrin e transflutrin; "inseciticidas de éteres piretróides" tais como etofenprox, flufenprox, halfen- prox, protrifenbuto e silafluofen; "inseciticidas de pirimidinaminas" tais como flufenerim e pirimidifeno; "inseciticidas de pirróis" tais como clorfenapir; "inse- ticidas de ácido tetrônico tais como espirodiclofeno, espiromesifeno e espiro- tetramat; "inseticidas de tiouréias" tais como diafentiuron; "inseticidas de u- réia" tais como flucofuron e sulcofuron; e inseticidas não classificados tais como AKD-3088, closantel, crotamiton, ciflumetofen, E2Y45, EXD, fenaza- flor, fenazaquin, fenoxacrim, fenpiroximato, FKI-1033, flubendiamida, HGW86, hidrametilnon, IKI-2002, isoprotiolano, malonoben, metaflumizona, metoxadiazona, nifluridida, NNI-9850, NNI-0101, pimetrozina, piridaben, piri- dalila, Qcide, rafoxanida, rinaxipir, SYJ-159, triarateno e triazamato e quais- quer combinações deles.
Alguns dos fungicidas que podem ser empregados de forma be- néfica em combinação com os compostos da presente invenção incluem: 2- (tiocianatometil-tio)-benzotiazol, 2-fenil-fenol, sulfato de 8-hidróxi-quinolina, Ampelomyces1 quisqualis, azaconazol, azoxistrobina, Bacillus subtilis, bena- laxil, benomil, bentiavalicarb-isopropila, sal sulfonato de benzil-amino- benzeno (BABS), bicarbonatos, bifenila, bismertiazol, bitertanol, blasticidina- S, bórax, mistura de Bordeaux, boscalid, bromuconazol, bupirimato, polissul- feto de cálcio, captafol, captan, carbendazim, carboxin, carpropamid, carvo- na, cloroneb, clorotalonil, clozolinato, Coniothyrium minitans, hidróxido de cobre, octanoato de cobre, oxicloreto de cobre, sulfato de cobre, sulfato de cobre (tribásico), óxido cuproso, ciazofamid, ciflufenamid, cimoxanil, ciproco- nazol, ciprodinil, dazomet, debacarb, etilenobis-(ditiocarbamato) diamoniacal, diclofluanid, diclorofeno, diclocimet, diclomezina, dicloran, dietofencarb, dife- noconazol, íon difenzoquat, diflumetorim, dimetomorf, dimoxistrobina, dinico- nazol, diniconazol-M,dinobuton, dinocap, difenilamina, ditianon, dodemorf, acetato de dodemorf, dodine, base livre de dodine, edifenfos, epoxiconazol, etaboxam, etoxiquin, etridiazol, famoxadona, fenamidona, fenarimol, fenbu- conazol, fenfuram, fenexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropi- morf, fentin, acetato de fentin, hidróxido de fentin, ferbam, ferimzona, fluazi- nam, fludioxonil, flumorf, fluopicolida, fluoroimida, fluoxastrobin, fluquincona- zol, flusilazol, flussulfamida, flutolanil, flutriafol, folpet, formaldeído, fosetil, fosetil-alumínio, fuberidazol, furalaxil, furametpir, guazatina, acetatos de guazatina, GY-81, hexacloro-benzeno, hexaconazol, himexazol, imazalil, sulfato de imazalil, imibenconazol, iminoctadina, triacetato de iminoctadina, tris-(albesilato) de iminoctadina, ipconazol, iprobenfos, iprodiona, iprovali- carb, isoprotiolano, kasugamicina, cloridrato de casugamicina hidratado, cre- soxim-metila, mancopper, mancozeb, maneb, mepanipirim, mepronil, cloreto mercúrico, óxido mercúrico, cloreto mercuroso, metalaxil, mefeno- xam, metalaxil-M, metam, metam-amônio, metam-potássio, metam-sódio, metconazol, metassulfocarb, iodeto de metila, isotiocianato de metila, meti- ram, metominostrobina, metrafenona, mildiomicina, miclobutanil, nabam, ni- trotal-isopropila, nuarimol, octilinona, ofurace, ácido oléico (ácidos graxos), orisastrobina, oxadixil, oxina-cobre, fumarato de oxpoconazol, oxicarboxina, pefurazoato, penconazol, pencicuron, pentaclorofenol, Iaurato de pentacloro- fenila, pentiopirad, acetato de fenil-mercúrio, ácido fosfônico, ftalida, picoxis- trobina, polioxina B, polioxinas, polioxorim, bicarbonato de potássio, sulfato de hidroxiquinolina potássico, probenazol, procloraz, procimidona, propamo- carb, cloridrato de propamocarb, propiconazol, propineb, proquinazid, protio- conazol, piraclostrobina, pirazofos, piributicarb, pirifenox, pirimetanil, piroqui- Ion1 quinoclamina, quinoxifeno, quintozeno, extrato de Reynoutria sachali- nensis, siltiofam, simeconazol, 2-fenilfenóxido de sódio, bicarbonato de só- dio, pentaclorofenóxido de sódio, espiroxamina, enxofre, SYP-Z071, óleos de alcatrão, tebuconazol, tecnazeno, tetraconazol, tiabendazol, tifluzamida, tiofanato-metila, tiram, tiadinil, tolclofos-metila, tolilfluanid, triadimefon, tria- dimenol, triazóxido, triciciazol, tridemorf, trifloxistrobina, triflumizol, triforina, triticonazol, validamicina, vinclozolin, zineb, ziram, zoxamida, Candida oleo- phila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantean, Strep- tomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dicloro-fenil)-2-(metóxi- metil)-succinimida, 1,2-dicloro-propano, 1,3-dicloro-1,1,3,3-tetraflúor-acetona hidratada, 1-cloro-2,4-dinitronaftaleno, 1-cloro-2-nitropropano, 2-(2- heptadecil-2-imidazolin-1-il)-etanol, 1,1,4,4-tetraóxido de 2,3-diidro-5-fenil- 1,4-ditiino, acetato de 2-metóxi-etil-mercúrio, cloreto de 2-metóxi-etil- mercúrio, silicato de 2-metóxi-etil-mercúrio, 3-(4-cloro-fenil)-5-metil- rhodanina, 4-(2-nitroprop-1-enil)-fenil tiocianateme: ampropilfos, anilazine, azitiram, polissulfeto de bário, Bayer 32394, benodanil, benquinox, bentalu- ron, benzamacril; benzamacril-isobutila, benzamorf, binapacril, sulfato de bis- (metil-mercúrio), óxido de bis-(tributil-estanho), butiobato, sulfato de cromato de cádmio cálcio zinco, carbamorf, CECA, clobentiazona, cloraniformetan, clorfenazol, clorquinox, climbazol, bis(3-fenilsalicilato) de cobre, cromato de cobre e zinco, cufraneb, sulfato de hidrazínio cúprico, cuprobam, ciclafura- mid, cipendazol, ciprofuram, decafentin, diclona, diclozolina, diclobutrazol, dimetirimol, dinocton, dinossulfon, dinoterbon, dipiritiona, ditalimfos, dodicina, drazoxolon, EBP, ESBP, etaconazol, etem, etirim, fenaminossulf, fenapanil, fenitropan, fluotrimazol, furcarbanil, furconazol, furconazol-cis, furmeciclox, furofanato, gliodina, griseofulvina, halacrinato, Hercules 3944, hexiltiofos, ICIA0858, isopamfos, isovalediona, mebenil, mecarbinzida, metazoxolon, metfuroxam, diciandiamida de metil-mercúrio, metsulfovax, milneb, anidrido mucoclórico, miclozolin, N-3,5-diclorofeníl-succinimida, N-3- nitrofenilitaconimida, natamicina, N-etil-mercúrio-4-toluenossulfonanilida, bis- (dimetil-ditiocarbamato) de níquel, OCH, dimetil-ditiocarbamato de fenil- merúrio, nitrato de fenil-mercúrio, fosdifen, protiocarb; cloridrato de protio- carb, piracarbolid, piridinitril, piroxiclor, piroxifur, quinacetol; sulfato de quina- cetol, quinazamid, quinconazol, rabenzazol, salicilanilida, SSF-109, sultro- pen, tecoram, tiadifluor, ticiofeno, tioclorfenfim, tiofanato, tioquinox, tioximid, triamifos, triarimol, triazbutil, triclamida, urbacid, XRD-563, e zarilamid, e quaisquer combinações deles.
Alguns dos herbicidas que podem ser empregados em conjunto com os compostos da presente invenção incluem: "herbicidas de amidas" tais como alidoclor, beflubutamid, benzadox, benzipram, bromobutida, ca- fenstrol, CDEA, clorthiamida, ciprazol, dimetenamida, dimetenamida-P, dife- namida, epronaz, etnipromid, fentrazamida, flupoxam, fomesafen, halosafen, isocarbamid, isoxaben, napropamida, naptalam, petoxamid, propizamida, quinonamid e tebutam; "herbicidas de anilidas" tais como cloranocril, cisani- Iida1 clomeprop, cipromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidida, metamifop, monalida, naproanilida, penta- noclor, picolinafen e propanil; "herbicidas de aril-alaninas" tais como benzoil- prop, flamprop e flamprop-M; "herbicidas de cloroacetanilidas" tais como a- cetoclor, alaclor, butaclor, butenaclor, delaclor, dietatil, dimetaclor, metaza- clor, metolaclor, S-metolaclor, pretilaclor, propaclor, propisoclor, prinaclor, terbuclor, tenilclor e xilaclor; "herbiucidas de sulfoanilidas" tais como benzo- fluor, perfluidona, pirimissulfan e profluazol; "herbicidas de sulfonamidas" tais como asulam, carbasulam, fenasulam e orizalin; "herbicidas antibióticos" tais como bilanafos; "herbicidas de ácido benzóico" tais como cloramben, dicam- ba, 2,3,6-TBA e tricamba; "herbicidas de ácido pirimidiniloxibenzóico" tais como bispiribac e piriminobac; "herbicidas de ácido pirimidiniltiobenzóico" tais como piritiobac; "herbicidas de ácido ftálico" tais como clortal; "herbici- das de ácido picolínico" tais como aminopiralid, clopiralid e picloram; "herbi- cidas de ácido quinolinocarboxílico" tais como quinclorac e quinmerac; "her- bicidas arsênicos" tais como ácido cacodílico, CMA, DSMA, hexaflurato, MAA1 MAMA, MSMA, arsenito de potássio e arsenito de sódio; "herbicidas de benzoil-ciclo-hexanodiona" tais como mesotriona, sulcotriona, tefuriltriona e tembotriona; "herbicidas de alquil-sulfonato de benzofuranila" tais como benfuresato e etofumesato; "herbicidas de carbamatos" tais como asulam, carboxazol clorprocarb, diclormato, fenasulam, karbutilato e terbucarb; "her- bicidas de carb anilatos" tais como barban, BCPC, carbasulam, carbetamida, CEPC, clorbufam, clorprofam, CPPC, desmedifam, fenisofam, fenmedifam, fenmedifam-etila, profam e swep; "herbicidas de ciclo-hexano oxima" tais como aloxidim, butroxidim, cletodim, cloproxidim, cicloxidim, profoxidim, se- toxidim, tepraloxidim e tralkoxidim; "herbicidas de ciclo-propil-isoxazol tais como isoxaclortol e isoxaflutol; "herbicidas de dicarboximidas" tais como benzfendizona, cinidon-etila, flumezin, flumiclorac, flumioxazin e flumipropin; "herbicidas de dimitroanilina" tais como benfluralin, butralin, dinitramina, etal- fluralina, flucloralina, isopropalina, metalpropalina, nitralina, orizalina, pendi- metalina, prodiamina, profluralina e trifluralina; "herbicidas de dinitrofenol" tais como dinofenato, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofe- no e medinoterb; "herbicidas de difenil-éteres" tais como etoxifeno; "herbici- das de nitrofenil-éteres" tais como acifluorfeno, aclonifeno, bifenox, clometo- xifcno, clornitrofeno, etnipromid, fluorodifeno, fluoroglicofeno, fluoronitrofeno, fomesafen, furiloxifeno, halosafeno, lactofeno, nitrofeno, nitrofluorfeno e oxi- fluorfeno; "herbicidas de ditiocarbamatos" tais como dazomet e metam; "her- bicidas alifáticos halogenados" tais como alorac, cloropon, dalapon, flupro- panato, hexacloroacetona, iodo-metano, brometo de metila, ácido monoclo- ro-acético, SMA e TCA; "herbicidas de imidazolinonas" tais como imazame- tabenz, imazamox, imazapic, imazapir, imazaquin e imazetapir; "herbicidas inorgânicos" tais como sulfamato de amônio, bórax, clorato de cálcio, sulfato de cobre, sulfato ferroso, azida de potássio, cianato de potássio, azida de sódio, clorato de sódio, e ácido sulfúrico; "herbicidas de nitrilas" tais como bromobonil, bromoxinil, cloroxinil, diclobenil, iodobonil, ioxinil e piraclonil; "herbicidas organofosforados" tais como amiprofos-metila, anilofos, bensuli- de, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamina, glufosinato, gli- fosato e piperofos; "herbicidas de fenóxi" tais como bromofenoxim, clome- prop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol e trifopsima; "herbicidas fenoxiacéticos" tais como 4-CPA, 2,4-D, 3,4-DA, MC- PA, MCPA-tioetila e 2,4,5-T; "herbicidas fenoxibutíricos" tais como 4-CPB, 2,4-DB, 3,4-DB, MCPB e 2,4,5-TB; "herbicidas fenoxipropiônicos" tais como cloprop, 4-CPP, diclorprop, diclorprop-P, 3,4-DP, fenoprop, mecoprop e me· coprop-P; "herbicidas arilóxi-fenóxi-propiônicos" tais como clorazifop, clodi- nafop, clofop, cialofop, diclofop, fenoxaprop, fenoxaprop-P, fentiaprop, fluazi- fop, fluazifop-P, haloxifop, haloxifop-P, isoxapirifop, metamifop, propaquiza- fop, quizalofop, quizalofop-P e trifop; "herbicidas de fenilenodiaminas" tais como dinitramina e prodiamina; "herbicidas de pirazolila" tais como benzofe- nap, pirazolinato, pirassulfotol, pirazoxifeno, piroxassulfona e topramezona; "herbicidas de pirazolil-fenila! Tais como fluazolato e piraflufeno; "herbicidas de piridazinas" tais como credazina, piridafol e piridato; "herbicidas de pirida- zinonas" tais como brompirazon, cloridazon, dimidazon, flufenpir, metflura- zon, norflurazon, oxapirazon e pidanon; "herbicidas de piridinas" tais como aminopiralid, cliodinato, clopiralid, ditiopir, fluroxipir, haloxidina, picloram, pi- colinafeno, piriclor, tiazopir e triclopir; "herbicidas de pirimidinodiaminas" tais como iprimidam e tioclorim; "herbicidas de amônio quaternário" tais como ciperquat, dietamquat, difenzoquat, diquat, morfamquat e paraquat; "herbici- das de tiocarb amatos" tais como butilato, cicloato, di-alato, EPTC, espro- carb, etiolato, isopolinato, metiobencarb, molinato, orbencarb, pebulato, prossulfocarb, piributicarb, sulfalato, tiobencarb, tiocarbazil, trialato e verno- lato; "herbicidas de tiocarbonatos" tais como dimexano, EXD e proxan; "her- bicidas de tiouréia" tais como metiuron; "herbicidas de triazinas" tais como dipropetrin, triaziflam e triidroxitriazina; "herbicidas de clorotriazinas" tais co- mo atrazina, clorazina, cianazina, ciprazina, eglinazina, ipazina, mesoprazi- na, prociazina, proglinazina, propazina, sebutilazina, simazina, terbutilazina e trietazina; "herbicidas de metóxi-triazinas" tais como atraton, metometon, prometon, secbumeton, simeton e terbumeton; "herbicidas de metil- tiotriazinas" tais como ametrin, aziprotrina, cianatrin, desmetrin, dimetame- trin, metoprotrina, prometrin, simetrin e terbutrin; "herbicidas de triazinonas" tais como ametridiona, amibuzin, hexazinona, isometiozin, metamitron e me- tribuzin; "herbicidas de trizóis" tais como amitrol, cafenstrol, epronaz e flupo- xam; "herbicidas de triazolonas" tais como amicarbazona, bencarbazona, carfentrazona, flucarbazona, propoxicarbazona, sulfentrazona e tiencarba- zona-metila; "herbicidas de triazolopirimidinas" tais como cloransulam, diclo- sulam, florasulam, flumetsulam, metosulam, penoxsulam and piroxsulam; "herbicidas de uracila" tais como butafenacil, bromacil, flupropacil, isocil, Ie- nacil e terbacil; "3-fenil-uracilas"; "herbicidas de uréia" tais como benztiazu- ron, cumiluron, cicluron, dicloraluréia, diflufenzopir, isonoruron, isouron, me- tabenztiazuron, monisouron e noruron; "herbicidas de fenil-uréia" tais como anisuron, buturon, clorbromuron, cloreturon, clorotoluron, cloroxuron, daimu- ron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluotiuron, isopro- turon, linuron, metiuron, metildimron, metobenzuron, metobromuron, metoxu- ron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron e tidiazuron; "herbicidas de pirimidinil-sulfonil-uréia" tais como a- midossulfuron, azimsulfuron, bensulfuron, clorimuron, ciclossulfamuron, eto- xissulfuron, flazassulfuron, flucetossulfuron, flupirsulfuron, foramsulfuron, halossulfuron, imazossulfuron, mesossulfuron, nicossulfuron, ortossulfamu- ron, oxassulfuron, primissulfuron, pirazossulfuron, rimsulfuron, sulfometuron, sulfossulfuron e triflcxissulfuron; "herbicidas de triazinil-silfonil-uréia" tais como clorsulfuron, cinossulfuron, etametsulfuron, iodossulfuron, metsulfuron, prossulfuron, tifensulfuron, triassulfuron, tribenuron, triflussulfuron e tritossul- furon; "herbicidas de tiadiazolil-uréia" tais como butiuron, etidimuron, tebutiu- ron, tiazafluron e tidiazuron; e "herbicidas não classificados" tais como acro- leína, álcool alílico, azafenidin, benazolin, bentazona, benzobiciclon, butida- zol, cianamida de cálcio, cambendiclor, clorfenac, clorfenprop, clorflurazol, clorflurenol, cinmetilin, clomazona, CPMF, cresol, orto-dicloro-benzeno, di- mepiperato, endotal, fluoromidina, fluridona, flurocloridona, flurtamona, flutia- cet, indanofan, metazol, isotiocianato de metila, nipiraclofen, OCH, oxadiar- gil, oxadiazon, oxaziclomefona, pentaclorofenol, pentoxazona, acetato de fenil-mercúrio, pinoxaden, prossulfalin, piribenzoxim, piriftalid, quinoclamina, rhodetanil, sulglicapin, tidiazimin, tridifano, trimeturon, tripropindan e tritac.
Claims (10)
1. Compostos da fórmula (I) <formula>formula see original document page 52</formula> em que Het representa: <formula>formula see original document page 52</formula> X representa halogênio, alquila de CrC4l halo-alquila de CrC4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, alcóxi de Cr C4, halo-alcóxi de CrC4, CN1 NO2, SOmR6, onde m é um número inteiro en- tre O e 2, COOR4 ou CONR4R5; Y representa hidrogênio, halogênio, alquila de CrC4, halo-alquila de C1-C4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, alcóxi de CrC4, halo-alcóxi de CrC4, CN1 NO2, SOmR1, onde m é um núme- ro inteiro entre O e 2, COOR41 CONR4R5, arila ou heteroarila; Z representa halo-alquila de CrC4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, halo-alcóxi de CrC4, CN, NO2, SOmR1, onde m é um número inteiro entre O e 2, COOR4 ou CONR4R5; η é um número inteiro entre O e 3; L representa uma ligação simples, -CH2-, ou -CH(CH2)p-, onde ρ é um número inteiro entre 1 e 3, e R11 S e L ou R2, L e o carbono comum ao qual eles estão anexados são juntados para representar um anel com 4, 5 ou 6 membros e até, porém não mais do que 1 heteroátomo; R1 representa alquila de CrC4, halo-alquila de CrC4, alquenila de C3-C6, alquinila de C3-C6, halo-alquenila de C3-C6, aril-alquila, hetaroaril- alquila, ou, alternativamente, é juntado com L ou R2 para formar um anel com 4, 5, ou 6 membros, saturado; R2 e R3 representam independentemente hidrogênio, halogênio, alquila de CrC4, halo-alquila de C1-C4, alquenila de C2-C4, alquinila de C2- C4, halo-alquenila de C2-C4, alcóxi de CrC4, halo-alcóxi de CrC4, CN, SO- mR6, onde m é um número inteiro entre O e 2, COOR4, CONR4R5, aril-alquila ou heteroaril-alquila, ou, alternativamente, R2 e R3 e o carbono comum ao qual eles estão anexados formam um anel com 3 a 6 membros, ou R2 e R3 juntados formam um anel com 4, 5, ou 6 membros, saturado; R4 e R5 representam independentemente hidrogênio, alquila de CrC4, halo-alquila de C1-C4, alquenila de C3-C6, alquinila de C3-C6, halo- alquenila de C3-C6,arila, heteroarila, aril-alquila ou heteroaril-alquila; R6 representa alquila de C1-C4, halo-alquila de C1-C4, alquenila de C3-C6, alquinila de C3-C6, halo-alquenila de C3-C6, aril-alquila, heteroaril- alquila; e Q representa NO2 ou CN.
2. Composto, de acordo com a reivindicação 1, onde Q repre- senta CN.
3. Composto, de acordo com a reivindicação 1, onde R2 e R3 representam independentemente hidrogênio ou alquila de CrC4, ou R2 e R3 e o carbono comum ao qual eles estão anexados formam um anel com 3 a 6 membros.
4. Composto, de acordo com a reivindicação 1, onde Het repre- senta em que Y representa hidrogênio, halogênio, alquila de CrC4, halo-alquila de C1-C4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, alcóxi de CrC4, halo-alcóxi de C1-C4, CN, NO2, SOmR1, onde m = O - 2, CO- OR4, CONR4R5, arila ou heteroarila; e Z representa halo-alquila de C1-C4, alquenila de C2-C4, alquinila de C2-C4, halo-alquenila de C2-C4, halo-alcóxi de C1-C4, CN, NO2, SOmR1, onde m = O - 2, COOR4 ou CONR4R5.
5. Composto, de acordo com a reivindicação 4, onde Y represen- ta hidrogênio e Z representa halo-alquila de C1-C2.
6. Composto, de acordo com a reivindicação 1, tendo a fórmula <formula>formula see original document page 54</formula> em que Het1 Q, R2 e R3 são como definidos anteriormente.
7. Composto, de acordo com a reivindicação 1, tendo a fórmula <formula>formula see original document page 54</formula> em que ρ é um número inteiro entre 1 e 3, e Het1 Q, R2 e R3 são como defi- nidos anteriormente.
8. Composto, de acordo com a reivindicação 1, tendo a fórmula <formula>formula see original document page 54</formula> em que ρ é um número inteiro entre 1 e 3, e Het e Q são como definidos an- teriormente.
9. Composição para controlar insetos, compreendendo um com- posto como definido na reivindicação 1, em combinação com um veículo fito- Iogicamente aceitável.
10. Método para controlar insetos, compreendendo aplicar a um local onde o controle é desejado uma quantidade inativadora de inseto de um composto como definido na reivindicação 1.
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-
2007
- 2007-02-08 TW TW096104609A patent/TWI387585B/zh not_active IP Right Cessation
- 2007-02-09 US US11/705,185 patent/US7754888B2/en active Active
- 2007-02-09 EP EP11161056A patent/EP2332913A1/en not_active Withdrawn
- 2007-02-09 CA CA2660757A patent/CA2660757C/en not_active Expired - Fee Related
- 2007-02-09 ES ES11161053.1T patent/ES2628039T3/es active Active
- 2007-02-09 MX MX2009002304A patent/MX2009002304A/es active IP Right Grant
- 2007-02-09 EP EP07750614A patent/EP2057121A2/en not_active Withdrawn
- 2007-02-09 BR BRPI0716262A patent/BRPI0716262B8/pt active IP Right Grant
- 2007-02-09 CN CN2007800407779A patent/CN101535261B/zh active Active
- 2007-02-09 WO PCT/US2007/003787 patent/WO2008030266A2/en active Application Filing
- 2007-02-09 EP EP11160995A patent/EP2336110A1/en not_active Withdrawn
- 2007-02-09 JP JP2009526585A patent/JP5266226B2/ja active Active
- 2007-02-09 EP EP11161053.1A patent/EP2338882B1/en active Active
- 2007-02-09 CN CN2012100707884A patent/CN102633712A/zh active Pending
- 2007-02-09 KR KR1020097004252A patent/KR101364320B1/ko active IP Right Grant
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2010
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Also Published As
Publication number | Publication date |
---|---|
HK1135982A1 (en) | 2010-06-18 |
WO2008030266A3 (en) | 2008-08-07 |
KR101364320B1 (ko) | 2014-02-18 |
ES2628039T3 (es) | 2017-08-01 |
KR20090043543A (ko) | 2009-05-06 |
CA2660757C (en) | 2014-06-03 |
EP2338882B1 (en) | 2017-06-07 |
EP2336110A1 (en) | 2011-06-22 |
EP2338882A1 (en) | 2011-06-29 |
CN101535261A (zh) | 2009-09-16 |
WO2008030266A2 (en) | 2008-03-13 |
BRPI0716262B1 (pt) | 2015-08-04 |
US7754888B2 (en) | 2010-07-13 |
JP2010502605A (ja) | 2010-01-28 |
CA2660757A1 (en) | 2008-03-13 |
US8188292B2 (en) | 2012-05-29 |
US20100234398A1 (en) | 2010-09-16 |
EP2332913A1 (en) | 2011-06-15 |
TW200812967A (en) | 2008-03-16 |
TWI387585B (zh) | 2013-03-01 |
JP5266226B2 (ja) | 2013-08-21 |
US20080280915A1 (en) | 2008-11-13 |
EP2057121A2 (en) | 2009-05-13 |
CN101535261B (zh) | 2012-06-20 |
CN102633712A (zh) | 2012-08-15 |
BRPI0716262B8 (pt) | 2022-06-28 |
MX2009002304A (es) | 2009-03-13 |
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