BR112019018238B1 - Composto, composição agroquímica, método de controle ou prevenção da infestação de plantas úteis por microrganismos fitopatogênicos e uso do referido composto como um fungicida - Google Patents

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Publication number

BR112019018238B1

BR112019018238B1 BR112019018238-1A BR112019018238A BR112019018238B1 BR 112019018238 B1 BR112019018238 B1 BR 112019018238B1 BR 112019018238 A BR112019018238 A BR 112019018238A BR 112019018238 B1 BR112019018238 B1 BR 112019018238B1

Authority

BR

Brazil

Prior art keywords

methyl

compound

ccn

alternative name

formula

Prior art date

2017-03-03

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 238
• 239000000417 fungicide Substances 0.000 title claims abstract description 69
• 238000000034 method Methods 0.000 title claims description 77
• 230000000855 fungicidal effect Effects 0.000 title claims description 19
• 230000003032 phytopathogenic effect Effects 0.000 title claims description 18
• 244000005700 microbiome Species 0.000 title claims description 13
• 206010061217 Infestation Diseases 0.000 title claims description 12
• 239000012872 agrochemical composition Substances 0.000 title claims description 4
• 244000038559 crop plants Species 0.000 title description 14
• 230000002265 prevention Effects 0.000 title description 5
• -1 hydroxy, amino Chemical group 0.000 claims description 223
• 239000000203 mixture Substances 0.000 claims description 101
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 239000004480 active ingredient Substances 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 239000000460 chlorine Substances 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 239000011737 fluorine Chemical group 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
• QKUHTUUPBXLHEA-UHFFFAOYSA-N [H]N[Cl]C#N Chemical group [H]N[Cl]C#N QKUHTUUPBXLHEA-UHFFFAOYSA-N 0.000 claims description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 244000045561 useful plants Species 0.000 claims 1
• 239000000575 pesticide Substances 0.000 abstract description 8
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• 231100000765 toxin Toxicity 0.000 description 52
• 108700012359 toxins Proteins 0.000 description 52
• 239000000126 substance Substances 0.000 description 46
• 229910052760 oxygen Inorganic materials 0.000 description 40
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• 150000003254 radicals Chemical class 0.000 description 39
• 229910052717 sulfur Inorganic materials 0.000 description 38
• 238000009472 formulation Methods 0.000 description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 238000011161 development Methods 0.000 description 32
• 230000018109 developmental process Effects 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
• 239000000463 material Substances 0.000 description 28
• 239000007787 solid Substances 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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• 201000010099 disease Diseases 0.000 description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
• 239000002904 solvent Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 21
• 229920006395 saturated elastomer Polymers 0.000 description 19
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• 241000233866 Fungi Species 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 239000000243 solution Substances 0.000 description 18
• 239000002671 adjuvant Substances 0.000 description 17
• 229910052799 carbon Inorganic materials 0.000 description 17
• 240000008042 Zea mays Species 0.000 description 16
• 125000005842 heteroatom Chemical group 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 238000002360 preparation method Methods 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000004009 herbicide Substances 0.000 description 15
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
• 125000000753 cycloalkyl group Chemical group 0.000 description 14
• 235000019439 ethyl acetate Nutrition 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 230000014759 maintenance of location Effects 0.000 description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 244000068988 Glycine max Species 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 239000003112 inhibitor Substances 0.000 description 12
• 108090000623 proteins and genes Proteins 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 230000002538 fungal effect Effects 0.000 description 11
• 102000004169 proteins and genes Human genes 0.000 description 11
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 10
• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
• 241000238631 Hexapoda Species 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 125000003342 alkenyl group Chemical group 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 10
• 230000009261 transgenic effect Effects 0.000 description 10
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• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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• 125000000304 alkynyl group Chemical group 0.000 description 9
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 8
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