ES2700352T3 - Compuestos bicíclicos como pesticidas - Google Patents
Compuestos bicíclicos como pesticidas Download PDFInfo
- Publication number
- ES2700352T3 ES2700352T3 ES15801466T ES15801466T ES2700352T3 ES 2700352 T3 ES2700352 T3 ES 2700352T3 ES 15801466 T ES15801466 T ES 15801466T ES 15801466 T ES15801466 T ES 15801466T ES 2700352 T3 ES2700352 T3 ES 2700352T3
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- ES
- Spain
- Prior art keywords
- alkyl
- spp
- series
- formula
- optionally substituted
- Prior art date
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- 125000002619 bicyclic group Chemical group 0.000 title claims description 29
- 239000000575 pesticide Substances 0.000 title description 28
- -1 nitro, amino Chemical group 0.000 claims abstract description 269
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 224
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 239000001257 hydrogen Substances 0.000 claims abstract description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 123
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 116
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 97
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 90
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 85
- 239000001301 oxygen Substances 0.000 claims abstract description 85
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 82
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 68
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 64
- 150000002367 halogens Chemical class 0.000 claims abstract description 59
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 51
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 39
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 36
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 34
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 32
- 150000001721 carbon Chemical group 0.000 claims abstract description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 31
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 27
- 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 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims abstract description 17
- 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
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 10
- 125000002541 furyl group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- 125000005880 oxathiolanyl 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
- IIKUBFGKDMSATI-UHFFFAOYSA-N 3-(oxathiolan-3-yloxy)oxathiolane Chemical compound S1OCCC1OC1SOCC1 IIKUBFGKDMSATI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims abstract description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 5
- 125000005968 oxazolinyl 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
- DAGYVIDJCUSBGI-UHFFFAOYSA-N C1CCOSC1OC1SOCCC1 Chemical compound C1CCOSC1OC1SOCCC1 DAGYVIDJCUSBGI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims abstract description 4
- 125000004992 haloalkylamino 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
- 229910052717 sulfur Chemical group 0.000 claims description 52
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 46
- 239000011593 sulfur Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
- 241000607479 Yersinia pestis Species 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 150000003463 sulfur Chemical class 0.000 claims description 15
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 150000001768 cations Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 8
- 125000005108 alkenylthio group Chemical group 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 5
- 125000004457 alkyl amino carbonyl 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
- 125000005879 dioxolanyl 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
- 239000004094 surface-active agent Substances 0.000 claims description 4
- SWQJWGBHPSUNSM-UHFFFAOYSA-N 3-(oxathiocan-3-yloxy)oxathiocane Chemical compound C1CCCCOSC1OC1SOCCCCC1 SWQJWGBHPSUNSM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000006319 alkynyl amino 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
- 125000006254 cycloalkyl carbonyl 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
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 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
- DNNMCYZOLVTTCF-UHFFFAOYSA-N 3-(oxathiepan-3-yloxy)oxathiepane Chemical compound C1CCC(OC2CCCCOS2)SOC1 DNNMCYZOLVTTCF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000005091 alkenylcarbonylamino 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
- 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
- 125000005088 alkynylcarbonylamino group Chemical group 0.000 claims description 2
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls 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
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 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
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical class [H]O* 0.000 claims 1
- 102200127349 rs11547328 Human genes 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 57
- 125000005883 dithianyl group Chemical group 0.000 abstract description 2
- 125000005257 alkyl acyl group Chemical group 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 description 88
- 125000005843 halogen group Chemical group 0.000 description 69
- 239000000203 mixture Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 50
- 238000000034 method Methods 0.000 description 49
- 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 49
- 238000009472 formulation Methods 0.000 description 44
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 42
- 150000003254 radicals Chemical class 0.000 description 32
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 230000008569 process Effects 0.000 description 20
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 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
- 239000002253 acid Substances 0.000 description 14
- 239000000645 desinfectant Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 13
- 239000002671 adjuvant Substances 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 230000004224 protection Effects 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 125000004434 sulfur atom Chemical group 0.000 description 12
- 230000009261 transgenic effect Effects 0.000 description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 10
- 230000009471 action Effects 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 9
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- 229940052303 ethers for general anesthesia Drugs 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 238000003306 harvesting Methods 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 7
- 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
- 241000238421 Arthropoda Species 0.000 description 7
- 240000002791 Brassica napus Species 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 7
- 239000005799 Isopyrazam Substances 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 241000209149 Zea Species 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000193388 Bacillus thuringiensis Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229930191978 Gibberellin Natural products 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000003337 fertilizer Substances 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 239000003448 gibberellin Substances 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
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- 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 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
- 241000701366 unidentified nuclear polyhedrosis viruses Species 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 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
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14195948 | 2014-12-02 | ||
| PCT/EP2015/078056 WO2016087368A1 (de) | 2014-12-02 | 2015-11-30 | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2700352T3 true ES2700352T3 (es) | 2019-02-15 |
Family
ID=52002809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15801466T Active ES2700352T3 (es) | 2014-12-02 | 2015-11-30 | Compuestos bicíclicos como pesticidas |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20170260183A1 (enExample) |
| EP (1) | EP3227288B1 (enExample) |
| JP (1) | JP2017537914A (enExample) |
| CN (1) | CN107207497A (enExample) |
| BR (1) | BR112017011669A2 (enExample) |
| ES (1) | ES2700352T3 (enExample) |
| WO (1) | WO2016087368A1 (enExample) |
Families Citing this family (21)
| 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 |
| JP6740239B2 (ja) | 2015-03-12 | 2020-08-12 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | 複素環置換二環式アゾール殺有害生物剤 |
| EP3280713B1 (en) | 2015-04-09 | 2019-06-05 | FMC Corporation | Bicyclic pyrazole pesticides |
| MX2019000512A (es) | 2016-07-12 | 2019-05-02 | Bayer Cropscience Ag | Compuestos biciclicos como plaguicidas. |
| BR112019000735A2 (pt) * | 2016-07-15 | 2019-05-07 | Fmc Corporation | composto, composição, método para controlar uma praga de invertebrados e semente tratada |
| JOP20190278A1 (ar) | 2017-05-31 | 2019-11-28 | Novartis Ag | مركبات 5، 6-ثنائية الحلقة مندمجة وتركيبات لعلاج الأمراض الطفيلية |
| CN112262140B (zh) | 2018-06-06 | 2024-05-28 | 先正达农作物保护股份公司 | 具有含亚砜亚胺取代基的杀有害生物活性杂环衍生物 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020141135A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| CN116348458A (zh) | 2019-08-14 | 2023-06-27 | 因赛特公司 | 作为cdk2抑制剂的咪唑基嘧啶基胺化合物 |
| CN119930611A (zh) | 2019-10-11 | 2025-05-06 | 因赛特公司 | 作为cdk2抑制剂的双环胺 |
| CN112410808A (zh) * | 2020-10-04 | 2021-02-26 | 浙江埃森化学有限公司 | 含n-吡啶基吡唑的邻氨基苯甲酸酯类杀虫剂合成方法 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| EP4522598A1 (en) | 2022-05-11 | 2025-03-19 | PI Industries Ltd. | Bicyclic compounds and their use as pest control agents |
| WO2025202955A1 (en) | 2024-03-28 | 2025-10-02 | Pi Industries Ltd. | Fused bicyclic compounds and their use as pest control agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3050874T3 (pl) * | 2008-11-14 | 2019-07-31 | Merial Inc. | Wzbogacone enancjomerycznie aryloazol-2-ilocyjanoetyloaminowe związki pasożytobójcze |
| ES2626601T3 (es) * | 2010-06-28 | 2017-07-25 | Bayer Intellectual Property Gmbh | Compuestos heterocíclicos como pesticidas |
| US9908887B2 (en) * | 2012-12-21 | 2018-03-06 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
| WO2014126580A1 (en) * | 2013-02-15 | 2014-08-21 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| 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 |
-
2015
- 2015-11-30 EP EP15801466.2A patent/EP3227288B1/de not_active Not-in-force
- 2015-11-30 ES ES15801466T patent/ES2700352T3/es active Active
- 2015-11-30 US US15/531,471 patent/US20170260183A1/en not_active Abandoned
- 2015-11-30 CN CN201580075199.7A patent/CN107207497A/zh active Pending
- 2015-11-30 WO PCT/EP2015/078056 patent/WO2016087368A1/de not_active Ceased
- 2015-11-30 JP JP2017529033A patent/JP2017537914A/ja active Pending
- 2015-11-30 BR BR112017011669-3A patent/BR112017011669A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP3227288B1 (de) | 2018-08-29 |
| BR112017011669A2 (pt) | 2018-02-27 |
| JP2017537914A (ja) | 2017-12-21 |
| WO2016087368A1 (de) | 2016-06-09 |
| US20170260183A1 (en) | 2017-09-14 |
| EP3227288A1 (de) | 2017-10-11 |
| CN107207497A (zh) | 2017-09-26 |
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