BR112017002598B1 - Derivados heterocíclicos ativos do ponto de vista pesticida com substituintes contendo enxofre - Google Patents

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Publication number

BR112017002598B1

BR112017002598B1 BR112017002598-1A BR112017002598A BR112017002598B1 BR 112017002598 B1 BR112017002598 B1 BR 112017002598B1 BR 112017002598 A BR112017002598 A BR 112017002598A BR 112017002598 B1 BR112017002598 B1 BR 112017002598B1

Authority

BR

Brazil

Prior art keywords

spp

formula

alkyl

trifluoromethyl

methyl

Prior art date

2014-08-12

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• 125000001424 substituent group Chemical group 0.000 title claims description 56
• 229910052717 sulfur Inorganic materials 0.000 title abstract description 18
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract description 14
• 239000011593 sulfur Substances 0.000 title abstract description 12
• 125000000623 heterocyclic group Chemical group 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 303
• -1 stereoisomers Chemical class 0.000 claims abstract description 121
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 239000000203 mixture Substances 0.000 claims description 130
• 229910052736 halogen Inorganic materials 0.000 claims description 91
• 150000002367 halogens Chemical group 0.000 claims description 91
• 238000000034 method Methods 0.000 claims description 81
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 71
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 241000607479 Yersinia pestis Species 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 12
• 239000000463 material Substances 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 239000000758 substrate Substances 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 230000000361 pesticidal effect Effects 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 150000002431 hydrogen Chemical group 0.000 claims 4
• 238000002405 diagnostic procedure Methods 0.000 claims 1
• 238000001356 surgical procedure Methods 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 150000001204 N-oxides Chemical class 0.000 abstract description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 5
• 239000002917 insecticide Substances 0.000 abstract description 3
• 239000000575 pesticide Substances 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
• YJXNJQHBVKTWCC-UHFFFAOYSA-N (3-cyclopent-2-en-1-yl-2-methyl-4-oxocyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(C2C=CCC2)C(=O)C1 YJXNJQHBVKTWCC-UHFFFAOYSA-N 0.000 description 163
• 239000000243 solution Substances 0.000 description 93
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
• 235000019439 ethyl acetate Nutrition 0.000 description 69
• 239000000126 substance Substances 0.000 description 52
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 43
• 238000002360 preparation method Methods 0.000 description 39
• 239000007787 solid Substances 0.000 description 39
• 239000003053 toxin Substances 0.000 description 39
• 231100000765 toxin Toxicity 0.000 description 39
• 108700012359 toxins Proteins 0.000 description 39
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 35
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• 238000005481 NMR spectroscopy Methods 0.000 description 33
• 241000196324 Embryophyta Species 0.000 description 32
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
• 239000012074 organic phase Substances 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 238000011161 development Methods 0.000 description 27
• 230000018109 developmental process Effects 0.000 description 27
• 238000005160 1H NMR spectroscopy Methods 0.000 description 26
• 238000010898 silica gel chromatography Methods 0.000 description 25
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• 235000019198 oils Nutrition 0.000 description 24
• 229910052938 sodium sulfate Inorganic materials 0.000 description 24
• 235000011152 sodium sulphate Nutrition 0.000 description 24
• 241000244206 Nematoda Species 0.000 description 23
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
• 240000008042 Zea mays Species 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 21
• 239000002585 base Substances 0.000 description 21
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
• 239000004480 active ingredient Substances 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 19
• 125000000753 cycloalkyl group Chemical group 0.000 description 19
• 229920006395 saturated elastomer Polymers 0.000 description 19
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 18
• 241000238631 Hexapoda Species 0.000 description 18
• 239000003153 chemical reaction reagent Substances 0.000 description 18
• 229910052801 chlorine Inorganic materials 0.000 description 18
• 125000004122 cyclic group Chemical group 0.000 description 18
• 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 239000012267 brine Substances 0.000 description 16
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 16
• 229910000027 potassium carbonate Inorganic materials 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 15
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 15
• 235000005822 corn Nutrition 0.000 description 15
• 235000011181 potassium carbonates Nutrition 0.000 description 15
• 239000007858 starting material Substances 0.000 description 15
• 238000009472 formulation Methods 0.000 description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
• 108090000623 proteins and genes Proteins 0.000 description 13
• 241000894007 species Species 0.000 description 13
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• 241000193388 Bacillus thuringiensis Species 0.000 description 12
• 244000025254 Cannabis sativa Species 0.000 description 12
• 241000254173 Coleoptera Species 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 239000002671 adjuvant Substances 0.000 description 12
• 229910052786 argon Inorganic materials 0.000 description 12
• 229940097012 bacillus thuringiensis Drugs 0.000 description 12
• 125000000232 haloalkynyl group Chemical group 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 239000012312 sodium hydride Substances 0.000 description 12
• 229910000104 sodium hydride Inorganic materials 0.000 description 12
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 12
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 11
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 11
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 11
• 230000029936 alkylation Effects 0.000 description 11
• 238000005804 alkylation reaction Methods 0.000 description 11
• 239000008346 aqueous phase Substances 0.000 description 11
• 229910000024 caesium carbonate Inorganic materials 0.000 description 11
• 239000007789 gas Substances 0.000 description 11
• 102000004169 proteins and genes Human genes 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910000029 sodium carbonate Inorganic materials 0.000 description 11
• 230000009261 transgenic effect Effects 0.000 description 11
• 241000193830 Bacillus <bacterium> Species 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
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• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
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• 238000007792 addition Methods 0.000 description 10
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• DERZERIPTUNNFI-UHFFFAOYSA-N BrC=1C=C(C(=NC=1)C1=NC2=C(C(N(C(=C2)C(F)(F)F)C)=O)N1C)S(=O)(=O)CC Chemical compound BrC=1C=C(C(=NC=1)C1=NC2=C(C(N(C(=C2)C(F)(F)F)C)=O)N1C)S(=O)(=O)CC DERZERIPTUNNFI-UHFFFAOYSA-N 0.000 description 9
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• 125000003118 aryl group Chemical group 0.000 description 9
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• 239000002169 Metam Substances 0.000 description 6
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