ES2712211T3 - Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas - Google Patents
Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas Download PDFInfo
- Publication number
- ES2712211T3 ES2712211T3 ES14729923T ES14729923T ES2712211T3 ES 2712211 T3 ES2712211 T3 ES 2712211T3 ES 14729923 T ES14729923 T ES 14729923T ES 14729923 T ES14729923 T ES 14729923T ES 2712211 T3 ES2712211 T3 ES 2712211T3
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- Spain
- Prior art keywords
- alkyl
- cycloalkyl
- amino
- case
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000000895 acaricidal effect Effects 0.000 title claims description 9
- 239000000642 acaricide Substances 0.000 title claims description 5
- 125000005361 aryl sulfoxide group Chemical group 0.000 title description 5
- 239000002917 insecticide Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 666
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 334
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 318
- -1 hetarylcarbonyl Chemical group 0.000 claims abstract description 299
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 262
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 261
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 209
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 204
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 166
- 125000003118 aryl group Chemical group 0.000 claims abstract description 154
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 138
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 119
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims abstract description 119
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 96
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 90
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 90
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 90
- 239000001257 hydrogen Substances 0.000 claims abstract description 88
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 88
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 75
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 63
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 61
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 59
- 125000004429 atom Chemical group 0.000 claims abstract description 57
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 55
- 150000002367 halogens Chemical class 0.000 claims abstract description 55
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 53
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 52
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 52
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims abstract description 50
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 49
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 49
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims abstract description 48
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims abstract description 48
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 48
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 47
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 47
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 41
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract description 41
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 41
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 41
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 41
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract description 39
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 37
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims abstract description 37
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract description 37
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 37
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 37
- 125000004986 diarylamino group Chemical group 0.000 claims abstract description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 35
- 239000011593 sulfur Substances 0.000 claims abstract description 35
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 33
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims abstract description 33
- 239000001301 oxygen Substances 0.000 claims abstract description 33
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 32
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 31
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims abstract description 30
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 28
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 23
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 23
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims abstract description 22
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract description 21
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 17
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 16
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims abstract description 16
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims abstract description 16
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims abstract description 16
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 16
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 16
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims abstract description 16
- 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
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims abstract description 15
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 14
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims abstract description 14
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims abstract description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 13
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims abstract description 13
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims abstract description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 13
- 125000004992 haloalkylamino group Chemical group 0.000 claims abstract description 13
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims abstract description 12
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims abstract description 10
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 10
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 7
- 150000002829 nitrogen Chemical class 0.000 claims abstract description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 3
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims abstract description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract 2
- 239000011575 calcium Substances 0.000 claims description 200
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 108
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 93
- 229910052731 fluorine Inorganic materials 0.000 claims description 92
- 239000000460 chlorine Chemical group 0.000 claims description 88
- 229910052801 chlorine Inorganic materials 0.000 claims description 84
- 239000011737 fluorine Chemical group 0.000 claims description 76
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 69
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 67
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 57
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 39
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 39
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 37
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 37
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 36
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 25
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 23
- 125000004001 thioalkyl group Chemical group 0.000 claims description 21
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 20
- 125000004740 (C1-C6) haloalkylsulfanyl group Chemical group 0.000 claims description 19
- 125000004982 dihaloalkyl group Chemical group 0.000 claims description 19
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 15
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical group BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims description 7
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 7
- 108020001305 NR1 subfamily Chemical group 0.000 claims description 7
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims description 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 72
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 64
- 229910052794 bromium Inorganic materials 0.000 claims 28
- 239000003112 inhibitor Substances 0.000 claims 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 11
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 9
- 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 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 6
- 239000005799 Isopyrazam Substances 0.000 claims 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 241000193388 Bacillus thuringiensis Species 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims 4
- 229940097012 bacillus thuringiensis Drugs 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 claims 4
- XVTXMTOYQVRHSK-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-prop-2-enoxyethyl]imidazole;sulfuric acid Chemical compound OS(O)(=O)=O.ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 XVTXMTOYQVRHSK-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- MKIMSXGUTQTKJU-UHFFFAOYSA-N Propamocarb hydrochloride Chemical compound [Cl-].CCCOC(=O)NCCC[NH+](C)C MKIMSXGUTQTKJU-UHFFFAOYSA-N 0.000 claims 3
- 108010052164 Sodium Channels Proteins 0.000 claims 3
- 102000018674 Sodium Channels Human genes 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims 3
- CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims 3
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 3
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 claims 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims 3
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 claims 3
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims 3
- 235000005152 nicotinamide Nutrition 0.000 claims 3
- 239000011570 nicotinamide Substances 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 claims 3
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims 3
- 230000035806 respiratory chain Effects 0.000 claims 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 3
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 claims 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 claims 2
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 claims 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims 2
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 claims 2
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims 2
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- 229960000490 permethrin Drugs 0.000 claims 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 claims 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 claims 1
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 claims 1
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- 230000004260 plant-type cell wall biogenesis Effects 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 150000008117 polysulfides Polymers 0.000 claims 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 claims 1
- 229960003761 propamidine Drugs 0.000 claims 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims 1
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims 1
- 229940015367 pyrethrum Drugs 0.000 claims 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 claims 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 claims 1
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- 229960002132 pyrrolnitrin Drugs 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
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- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 claims 1
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- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 claims 1
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- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 claims 1
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- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 claims 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 claims 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims 1
- 229950004921 temefos Drugs 0.000 claims 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 claims 1
- 229960002722 terbinafine Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 claims 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 claims 1
- 239000004308 thiabendazole Substances 0.000 claims 1
- 235000010296 thiabendazole Nutrition 0.000 claims 1
- 229960004546 thiabendazole Drugs 0.000 claims 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 claims 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 claims 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 claims 1
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- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 claims 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 claims 1
- 230000014616 translation Effects 0.000 claims 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 claims 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 claims 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 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 claims 1
- 229960004740 voriconazole Drugs 0.000 claims 1
- 239000005943 zeta-Cypermethrin Substances 0.000 claims 1
- 229940048462 zinc phosphide Drugs 0.000 claims 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 claims 1
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 125000005362 aryl sulfone group Chemical group 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- AAXFXXDVLCDKPL-UHFFFAOYSA-N 4-[3-[3-(2h-triazol-4-yl)phenyl]sulfanylphenyl]-2h-triazole Chemical class C=1C=CC(C=2N=NNC=2)=CC=1SC(C=1)=CC=CC=1C1=CNN=N1 AAXFXXDVLCDKPL-UHFFFAOYSA-N 0.000 description 1
- VKDMORLIYFMPNN-UHFFFAOYSA-N 5-[3-[3-(1h-pyrazol-5-yl)phenyl]sulfanylphenyl]-1h-pyrazole Chemical class C=1C=CC(C2=NNC=C2)=CC=1SC(C=1)=CC=CC=1C=1C=CNN=1 VKDMORLIYFMPNN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910014585 C2-Ce Inorganic materials 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-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
- A01N43/48—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
- A01N43/64—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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
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- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/34—Ethylene-urea
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13172993 | 2013-06-20 | ||
| PCT/EP2014/062510 WO2014202505A1 (de) | 2013-06-20 | 2014-06-16 | Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide |
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| ES2712211T3 true ES2712211T3 (es) | 2019-05-09 |
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| ES14729923T Active ES2712211T3 (es) | 2013-06-20 | 2014-06-16 | Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas |
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| JP (1) | JP2016526538A (OSRAM) |
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| BR (1) | BR112015031155A2 (OSRAM) |
| ES (1) | ES2712211T3 (OSRAM) |
| WO (1) | WO2014202505A1 (OSRAM) |
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| BR112015031291A2 (pt) * | 2013-06-20 | 2017-07-25 | Bayer Cropscience Ag | derivados de sulfureto de arila e derivados de arilalquil sulfóxido como acaricidas e inseticidas |
| AR102942A1 (es) * | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
| ES2818608T3 (es) | 2016-07-12 | 2021-04-13 | Bayer Cropscience Ag | Compuestos bicíclicos como pesticidas |
| DK3683215T3 (da) | 2017-09-11 | 2023-08-28 | Sumitomo Chemical Co | Tetrazolinonforbindelse og anvendelse deraf |
| WO2019233321A1 (zh) * | 2018-06-05 | 2019-12-12 | 沈阳化工大学 | 一种三氟乙基硫醚(亚砜)取代苯类化合物及其用途 |
| CN111100049A (zh) | 2018-10-25 | 2020-05-05 | 沈阳中化农药化工研发有限公司 | 一种含硫联苯类化合物的制备方法 |
| US11292782B2 (en) | 2018-11-30 | 2022-04-05 | Nuvation Bio Inc. | Diarylhydantoin compounds and methods of use thereof |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN112142646B (zh) * | 2019-06-26 | 2022-08-09 | 沈阳中化农药化工研发有限公司 | 一种吡咯并芳环类化合物及其应用 |
| CN110879267A (zh) * | 2019-12-24 | 2020-03-13 | 金华市农产品质量综合监督检测中心 | 一种乙酰甲胺磷及代谢产物甲胺磷在叶菜中的动态降解分析方法 |
| CN111187188A (zh) * | 2020-01-08 | 2020-05-22 | 普济生物科技(台州)有限公司 | 一种取代的苯硫酚的合成方法 |
| CN113943238B (zh) | 2020-07-17 | 2022-11-01 | 沈阳中化农药化工研发有限公司 | 一种取代的苯硫醚类化合物及其应用 |
| KR20240038029A (ko) | 2021-07-27 | 2024-03-22 | 바이엘 악티엔게젤샤프트 | (2,2,2-트리플루오로에틸)설파닐아닐린 유도체의 제조 방법 |
| CN117049997B (zh) * | 2022-05-05 | 2025-12-05 | 帕潘纳(北京)科技有限公司 | 一种苯基三氟乙基硫醚(亚砜)类化合物及其用途 |
| CN116041232B (zh) * | 2022-12-31 | 2025-02-14 | 浙江工业大学 | 一种三氟乙基硫醚类杀螨剂中间体的制备方法 |
| WO2024153573A1 (de) | 2023-01-19 | 2024-07-25 | Bayer Aktiengesellschaft | Verfahren zur herstellung von (2,2,2-trifluorethyl)sulfanylanilin-derivaten |
| CN120136787A (zh) * | 2023-12-13 | 2025-06-13 | 青岛清原化合物有限公司 | 一种吡唑取代的芳基硫化物类化合物及其应用 |
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-
2014
- 2014-06-16 WO PCT/EP2014/062510 patent/WO2014202505A1/de not_active Ceased
- 2014-06-16 BR BR112015031155A patent/BR112015031155A2/pt not_active Application Discontinuation
- 2014-06-16 US US14/899,260 patent/US9981928B2/en active Active
- 2014-06-16 ES ES14729923T patent/ES2712211T3/es active Active
- 2014-06-16 EP EP14729923.4A patent/EP3010889B1/de not_active Not-in-force
- 2014-06-16 JP JP2016520406A patent/JP2016526538A/ja not_active Ceased
- 2014-06-16 CN CN201480045848.4A patent/CN105722830B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP3010889B1 (de) | 2018-10-03 |
| US20160130240A1 (en) | 2016-05-12 |
| JP2016526538A (ja) | 2016-09-05 |
| EP3010889A1 (de) | 2016-04-27 |
| CN105722830A (zh) | 2016-06-29 |
| WO2014202505A1 (de) | 2014-12-24 |
| BR112015031155A2 (pt) | 2017-07-25 |
| CN105722830B (zh) | 2019-06-04 |
| US9981928B2 (en) | 2018-05-29 |
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