ES2712908T3 - 2H-Pirazolo[4,3-b]piridinas como pesticidas - Google Patents
2H-Pirazolo[4,3-b]piridinas como pesticidas Download PDFInfo
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- ES2712908T3 ES2712908T3 ES15802117T ES15802117T ES2712908T3 ES 2712908 T3 ES2712908 T3 ES 2712908T3 ES 15802117 T ES15802117 T ES 15802117T ES 15802117 T ES15802117 T ES 15802117T ES 2712908 T3 ES2712908 T3 ES 2712908T3
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- alkyl
- spp
- series
- alkoxy
- residue
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- 239000000575 pesticide Substances 0.000 title description 29
- 150000003222 pyridines Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 227
- -1 nitro, amino Chemical group 0.000 claims abstract description 212
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 239000001257 hydrogen Substances 0.000 claims abstract description 126
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 126
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 116
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 98
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 94
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 92
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 86
- 239000001301 oxygen Substances 0.000 claims abstract description 81
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 80
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 70
- 150000002367 halogens Chemical class 0.000 claims abstract description 58
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 36
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 35
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 33
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 29
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 25
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 25
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 24
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims abstract description 15
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims abstract description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000002541 furyl group Chemical group 0.000 claims abstract description 9
- 125000005880 oxathiolanyl group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 6
- SWQJWGBHPSUNSM-UHFFFAOYSA-N 3-(oxathiocan-3-yloxy)oxathiocane Chemical compound C1CCCCOSC1OC1SOCCCCC1 SWQJWGBHPSUNSM-UHFFFAOYSA-N 0.000 claims abstract description 5
- IIKUBFGKDMSATI-UHFFFAOYSA-N 3-(oxathiolan-3-yloxy)oxathiolane Chemical compound S1OCCC1OC1SOCC1 IIKUBFGKDMSATI-UHFFFAOYSA-N 0.000 claims abstract description 5
- DAGYVIDJCUSBGI-UHFFFAOYSA-N C1CCOSC1OC1SOCCC1 Chemical compound C1CCOSC1OC1SOCCC1 DAGYVIDJCUSBGI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005879 dioxolanyl group Chemical group 0.000 claims abstract description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 5
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims abstract description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 5
- 125000004306 triazinyl group Chemical group 0.000 claims abstract description 5
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 5
- DNNMCYZOLVTTCF-UHFFFAOYSA-N 3-(oxathiepan-3-yloxy)oxathiepane Chemical compound C1CCC(OC2CCCCOS2)SOC1 DNNMCYZOLVTTCF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 38
- 229910052717 sulfur Chemical group 0.000 claims description 38
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 239000011593 sulfur Chemical group 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000003463 sulfur Chemical class 0.000 claims description 31
- 241000607479 Yersinia pestis Species 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 239000004606 Fillers/Extenders Substances 0.000 claims description 8
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005108 alkenylthio group Chemical group 0.000 claims description 8
- 150000001768 cations Chemical group 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical class F* 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 102200127349 rs11547328 Human genes 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical compound ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims description 5
- YKOWBJJOJNGCAD-SHYZEUOFSA-N [(2r,3s,5r)-3-hydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate Chemical compound O=C1N=C(NO)C=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 YKOWBJJOJNGCAD-SHYZEUOFSA-N 0.000 claims description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 150000002926 oxygen Chemical class 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000005367 heteroarylalkylthio group Chemical group 0.000 claims description 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims description 3
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 2
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006776 haloalkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 abstract description 7
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 abstract description 4
- 125000000532 dioxanyl group Chemical group 0.000 abstract description 3
- 125000005883 dithianyl group Chemical group 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 150000001721 carbon Chemical group 0.000 abstract 2
- 239000011575 calcium Substances 0.000 description 119
- 241000196324 Embryophyta Species 0.000 description 90
- 239000000203 mixture Substances 0.000 description 65
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 55
- 238000000034 method Methods 0.000 description 53
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 46
- 238000009472 formulation Methods 0.000 description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 37
- 241001465754 Metazoa Species 0.000 description 31
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 27
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 239000002253 acid Substances 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 19
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 18
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- 239000011737 fluorine Substances 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 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 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000645 desinfectant Substances 0.000 description 15
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 14
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 230000009261 transgenic effect Effects 0.000 description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
- 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 11
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- 230000004224 protection Effects 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
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- 229910052700 potassium Inorganic materials 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
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- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
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- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14195939 | 2014-12-02 | ||
| PCT/EP2015/078169 WO2016087422A1 (de) | 2014-12-02 | 2015-12-01 | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2712908T3 true ES2712908T3 (es) | 2019-05-16 |
Family
ID=52002806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15802117T Active ES2712908T3 (es) | 2014-12-02 | 2015-12-01 | 2H-Pirazolo[4,3-b]piridinas como pesticidas |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20180282319A1 (enExample) |
| EP (1) | EP3227290B1 (enExample) |
| JP (1) | JP2017537911A (enExample) |
| CN (1) | CN107207495A (enExample) |
| BR (1) | BR112017011656A2 (enExample) |
| ES (1) | ES2712908T3 (enExample) |
| WO (1) | WO2016087422A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI652014B (zh) | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| KR102536024B1 (ko) | 2015-03-12 | 2023-05-24 | 에프엠씨 코포레이션 | 헤테로환-치환 이환 아졸 살충제 |
| JP6857614B2 (ja) | 2015-04-09 | 2021-04-14 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | 二環式ピラゾール殺有害生物剤 |
| AU2017295745A1 (en) * | 2016-07-12 | 2019-01-31 | Bayer Cropscience Aktiengesellschaft | Bicyclic compounds as pest control agents |
| CN109890807B (zh) * | 2016-07-15 | 2023-04-04 | Fmc 公司 | 杂环取代的双环唑农药 |
| CN109963860A (zh) * | 2016-09-19 | 2019-07-02 | 拜耳作物科学股份公司 | 吡唑并[1,5-a]吡啶衍生物及其作为农药的用途 |
| EP4522598A1 (en) | 2022-05-11 | 2025-03-19 | PI Industries Ltd. | Bicyclic compounds and their use as pest control agents |
| UY41082A (es) | 2024-03-28 | 2025-08-29 | Pi Industries Ltd | Compuestos bicíclicos condensados y su uso como agentes de control de plagas |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0717641B2 (ja) * | 1986-03-31 | 1995-03-01 | 日産化学工業株式会社 | イミダゾリン誘導体、その製法および除草剤 |
| AR074024A1 (es) * | 2008-11-14 | 2010-12-15 | Merial Ltd | Compuesto de arilazol-2-il-cianoetilamino enantiomericamente enriquecidos, composicion plaguicida y su uso para prevenir la infeccion parasitaria |
| CN103119036B (zh) * | 2010-06-28 | 2018-05-08 | 拜耳知识产权有限责任公司 | 作为杀虫剂的杂环化合物 |
| WO2014126580A1 (en) * | 2013-02-15 | 2014-08-21 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US20180368404A1 (en) * | 2014-11-06 | 2018-12-27 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
-
2015
- 2015-12-01 WO PCT/EP2015/078169 patent/WO2016087422A1/de not_active Ceased
- 2015-12-01 BR BR112017011656-1A patent/BR112017011656A2/pt not_active Application Discontinuation
- 2015-12-01 EP EP15802117.0A patent/EP3227290B1/de not_active Not-in-force
- 2015-12-01 US US15/531,748 patent/US20180282319A1/en not_active Abandoned
- 2015-12-01 CN CN201580074522.9A patent/CN107207495A/zh active Pending
- 2015-12-01 ES ES15802117T patent/ES2712908T3/es active Active
- 2015-12-01 JP JP2017529017A patent/JP2017537911A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016087422A1 (de) | 2016-06-09 |
| US20180282319A1 (en) | 2018-10-04 |
| CN107207495A (zh) | 2017-09-26 |
| EP3227290B1 (de) | 2018-11-21 |
| JP2017537911A (ja) | 2017-12-21 |
| BR112017011656A2 (pt) | 2019-05-14 |
| EP3227290A1 (de) | 2017-10-11 |
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