BR112018001414B1 - Compostos derivados de 1, 2, 4-triazol do ponto de vista pesticida com substituintes contendo enxofre, composição pesticida, método para controle de pragas e método para aproteção de material de propagação de plantas do ataque por pragas - Google Patents
Compostos derivados de 1, 2, 4-triazol do ponto de vista pesticida com substituintes contendo enxofre, composição pesticida, método para controle de pragas e método para aproteção de material de propagação de plantas do ataque por pragas Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 360
- 239000000203 mixture Substances 0.000 title claims description 142
- 238000000034 method Methods 0.000 title claims description 118
- 241000607479 Yersinia pestis Species 0.000 title claims description 27
- 239000000463 material Substances 0.000 title claims description 14
- 239000000575 pesticide Substances 0.000 title abstract description 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 8
- 229910052717 sulfur Inorganic materials 0.000 title description 8
- 239000011593 sulfur Substances 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 106
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 230000000361 pesticidal effect Effects 0.000 claims description 7
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- -1 stereoisomers Chemical class 0.000 abstract description 139
- 150000001204 N-oxides Chemical class 0.000 abstract description 20
- 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 18
- 239000002917 insecticide Substances 0.000 abstract description 4
- 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 141
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 79
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 76
- 238000002360 preparation method Methods 0.000 description 76
- 239000007787 solid Substances 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 53
- 230000014759 maintenance of location Effects 0.000 description 52
- 239000000243 solution Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 49
- 238000005160 1H NMR spectroscopy Methods 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 239000003053 toxin Substances 0.000 description 39
- 231100000765 toxin Toxicity 0.000 description 39
- 108700012359 toxins Proteins 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000000126 substance Substances 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 37
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 239000002904 solvent Substances 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 32
- 229910052801 chlorine Inorganic materials 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 31
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- 229910052938 sodium sulfate Inorganic materials 0.000 description 28
- 235000011152 sodium sulphate Nutrition 0.000 description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 27
- 229910052794 bromium Inorganic materials 0.000 description 27
- 239000002253 acid Substances 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 23
- 239000012442 inert solvent Substances 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
- 238000011161 development Methods 0.000 description 21
- 230000018109 developmental process Effects 0.000 description 21
- 241000244206 Nematoda Species 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 20
- 238000001816 cooling Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 238000000746 purification Methods 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- 241000238631 Hexapoda Species 0.000 description 18
- 229910052740 iodine Inorganic materials 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 235000013311 vegetables Nutrition 0.000 description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 239000011630 iodine Substances 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- 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 16
- 229910000029 sodium carbonate Inorganic materials 0.000 description 16
- 241000894007 species Species 0.000 description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 235000011181 potassium carbonates Nutrition 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 229910052786 argon Inorganic materials 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 239000002671 adjuvant Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
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- 239000012044 organic layer Substances 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 13
- 241000254173 Coleoptera Species 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 150000008052 alkyl sulfonates Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 11
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 11
- 235000009973 maize Nutrition 0.000 description 11
- 239000007800 oxidant agent Substances 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- 230000009261 transgenic effect Effects 0.000 description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 10
- 244000025254 Cannabis sativa Species 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000005228 aryl sulfonate group Chemical group 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 125000004076 pyridyl group Chemical group 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 9
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- 238000007792 addition Methods 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
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- 239000000654 additive Substances 0.000 description 8
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
- 150000008041 alkali metal carbonates Chemical class 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 8
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- 230000001590 oxidative effect Effects 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
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- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- DZQBSWZVIZGETK-UHFFFAOYSA-N 4-[5-[6-(3-chloro-1,2,4-triazol-1-yl)-3-ethylsulfonylpyridin-2-yl]-4-methyl-1,2,4-triazol-3-yl]-6-(trifluoromethyl)pyrimidine Chemical compound ClC1=NN(C=N1)C1=CC=C(C(=N1)C=1N(C(=NN=1)C1=NC=NC(=C1)C(F)(F)F)C)S(=O)(=O)CC DZQBSWZVIZGETK-UHFFFAOYSA-N 0.000 description 6
- XOIFGWBEYMHQKV-UHFFFAOYSA-N 5-bromo-3-ethylsulfonyl-2-[4-methyl-5-[4-(trifluoromethyl)pyridin-2-yl]-1,2,4-triazol-3-yl]pyridine Chemical compound BrC=1C=C(C(=NC=1)C1=NN=C(N1C)C1=NC=CC(=C1)C(F)(F)F)S(=O)(=O)CC XOIFGWBEYMHQKV-UHFFFAOYSA-N 0.000 description 6
- LJLKPMJBRGBMKA-UHFFFAOYSA-N 5-ethenyl-3-ethylsulfonyl-2-[4-methyl-5-[4-(trifluoromethyl)pyridin-2-yl]-1,2,4-triazol-3-yl]pyridine Chemical compound C(C)S(=O)(=O)C=1C(=NC=C(C=1)C=C)C1=NN=C(N1C)C1=NC=CC(=C1)C(F)(F)F LJLKPMJBRGBMKA-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 6
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- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
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- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
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Classifications
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15178308 | 2015-07-24 | ||
| EP15178308.1 | 2015-07-24 | ||
| EP15186015.2 | 2015-09-21 | ||
| EP15186015 | 2015-09-21 | ||
| EP16154598 | 2016-02-08 | ||
| EP16154598.3 | 2016-02-08 | ||
| PCT/EP2016/067003 WO2017016910A1 (en) | 2015-07-24 | 2016-07-18 | Pesticidally active 1,2,4-triazole derivatives with sulphur containing substituents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112018001414A2 BR112018001414A2 (pt) | 2018-09-11 |
| BR112018001414B1 true BR112018001414B1 (pt) | 2022-02-22 |
Family
ID=56413685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112018001414-1A BR112018001414B1 (pt) | 2015-07-24 | 2016-07-18 | Compostos derivados de 1, 2, 4-triazol do ponto de vista pesticida com substituintes contendo enxofre, composição pesticida, método para controle de pragas e método para aproteção de material de propagação de plantas do ataque por pragas |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10292391B2 (https=) |
| EP (1) | EP3325470B1 (https=) |
| JP (1) | JP6862416B2 (https=) |
| CN (1) | CN107849027B (https=) |
| BR (1) | BR112018001414B1 (https=) |
| ES (1) | ES2895729T3 (https=) |
| WO (1) | WO2017016910A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| US11039617B2 (en) | 2013-01-30 | 2021-06-22 | Agrofresh Inc. | Large scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness |
| WO2017155879A1 (en) | 2016-03-07 | 2017-09-14 | Agrofresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| JP2019513739A (ja) | 2016-04-07 | 2019-05-30 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する殺有害生物的に活性な複素環式誘導体 |
| ES2913985T3 (es) * | 2016-09-15 | 2022-06-07 | Nippon Soda Co | Compuesto de diaril-azol y formulación para el control de organismos nocivos |
| CN109456902B (zh) * | 2018-12-25 | 2020-07-07 | 广西大学 | 一株白及内生真菌1-n2及其应用 |
| US20250019362A1 (en) | 2021-11-19 | 2025-01-16 | Nippon Soda Co., Ltd. | Method for producing 2-heteroarylpyridine compound |
| WO2023090344A1 (ja) | 2021-11-19 | 2023-05-25 | 日本曹達株式会社 | ２－ヘテロアリールピリジン化合物の製造方法 |
| EP4680028A1 (en) | 2023-03-14 | 2026-01-21 | Syngenta Crop Protection AG | Control of pests resistant to insecticides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1123287E (pt) | 1998-10-23 | 2003-12-31 | Dow Agrosciences Llc | 1-(piridil substituido)-1,2,4-triazoles insecticidas |
| AU2005230864A1 (en) * | 2004-03-29 | 2005-10-20 | Merck Sharp & Dohme Corp. | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| EP1799659A1 (en) * | 2004-10-13 | 2007-06-27 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| JP2015131783A (ja) * | 2014-01-14 | 2015-07-23 | 株式会社日本ファインケム | アリール−１，２，４−トリアゾール誘導体の製造方法 |
| EP3122740B1 (en) * | 2014-03-28 | 2019-09-18 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulphur containing substituents |
| JP6493394B2 (ja) * | 2014-04-24 | 2019-04-03 | 住友化学株式会社 | ジアリール−アゾール化合物 |
-
2016
- 2016-07-18 BR BR112018001414-1A patent/BR112018001414B1/pt active IP Right Grant
- 2016-07-18 ES ES16739169T patent/ES2895729T3/es active Active
- 2016-07-18 EP EP16739169.7A patent/EP3325470B1/en active Active
- 2016-07-18 JP JP2018503527A patent/JP6862416B2/ja not_active Expired - Fee Related
- 2016-07-18 US US15/747,215 patent/US10292391B2/en active Active
- 2016-07-18 CN CN201680043434.7A patent/CN107849027B/zh active Active
- 2016-07-18 WO PCT/EP2016/067003 patent/WO2017016910A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3325470B1 (en) | 2021-08-18 |
| US10292391B2 (en) | 2019-05-21 |
| WO2017016910A1 (en) | 2017-02-02 |
| BR112018001414A2 (pt) | 2018-09-11 |
| EP3325470A1 (en) | 2018-05-30 |
| US20180213781A1 (en) | 2018-08-02 |
| ES2895729T3 (es) | 2022-02-22 |
| JP2018527325A (ja) | 2018-09-20 |
| CN107849027B (zh) | 2021-03-12 |
| CN107849027A (zh) | 2018-03-27 |
| JP6862416B2 (ja) | 2021-04-21 |
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Legal Events
| Date | Code | Title | Description |
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| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 18/07/2016, OBSERVADAS AS CONDICOES LEGAIS. |