ES2468794T3 - Derivados de sulfuro sustituidos con 3-triazolilfenilo como acaricidas e insecticidas - Google Patents
Derivados de sulfuro sustituidos con 3-triazolilfenilo como acaricidas e insecticidas Download PDFInfo
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- ES2468794T3 ES2468794T3 ES10744515.7T ES10744515T ES2468794T3 ES 2468794 T3 ES2468794 T3 ES 2468794T3 ES 10744515 T ES10744515 T ES 10744515T ES 2468794 T3 ES2468794 T3 ES 2468794T3
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- Prior art keywords
- methyl
- spp
- carboxamide
- phenyl
- pyrazol
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- -1 3-triazolylphenyl Chemical group 0.000 title claims abstract description 134
- 230000000895 acaricidal effect Effects 0.000 title claims description 9
- 239000000642 acaricide Substances 0.000 title claims description 8
- 239000002917 insecticide Substances 0.000 title description 12
- 125000000101 thioether group Chemical group 0.000 title 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 150000003568 thioethers Chemical class 0.000 claims abstract description 14
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract description 11
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 69
- 241000196324 Embryophyta Species 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000003112 inhibitor Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- 238000002360 preparation method Methods 0.000 claims description 37
- 230000000694 effects Effects 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 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 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 244000000054 animal parasite Species 0.000 claims description 10
- 150000003852 triazoles Chemical class 0.000 claims description 10
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 9
- 229940097012 bacillus thuringiensis Drugs 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 241000238631 Hexapoda Species 0.000 claims description 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- 150000002429 hydrazines Chemical class 0.000 claims description 8
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 239000000556 agonist Substances 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000035515 penetration Effects 0.000 claims description 6
- 230000035806 respiratory chain Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 5
- 150000002019 disulfides Chemical class 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- 235000016709 nutrition Nutrition 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000005660 Abamectin Substances 0.000 claims description 4
- 102000012440 Acetylcholinesterase Human genes 0.000 claims description 4
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 229920002101 Chitin Polymers 0.000 claims description 4
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 4
- 102000015782 Electron Transport Complex III Human genes 0.000 claims description 4
- 108010024882 Electron Transport Complex III Proteins 0.000 claims description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 102000034337 acetylcholine receptors Human genes 0.000 claims description 4
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims description 4
- 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 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 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 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229960002125 enilconazole Drugs 0.000 claims description 4
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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 description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 4
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 claims description 4
- 230000010627 oxidative phosphorylation Effects 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000029058 respiratory gaseous exchange Effects 0.000 claims description 4
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 3
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 239000005821 Propamocarb Substances 0.000 claims description 3
- 150000001411 amidrazones Chemical class 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
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- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- WBTCZEPSIIFINA-MSFWTACDSA-J dipotassium;antimony(3+);(2r,3r)-2,3-dioxidobutanedioate;trihydrate Chemical compound O.O.O.[K+].[K+].[Sb+3].[Sb+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O.[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O WBTCZEPSIIFINA-MSFWTACDSA-J 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
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- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 3
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- 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 description 3
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 3
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- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 claims description 2
- ATROHALUCMTWTB-WYMLVPIESA-N (z)-n-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide Chemical compound CCOP(=S)(OCC)O\N=C(/C#N)C1=CC=CC=C1 ATROHALUCMTWTB-WYMLVPIESA-N 0.000 claims description 2
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 claims description 2
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims description 2
- IHGSAQHSAGRWNI-UHFFFAOYSA-N 1-(4-bromophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Br)C=C1 IHGSAQHSAGRWNI-UHFFFAOYSA-N 0.000 claims description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 2
- RQTVIKMRXYJTDX-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-phenylpiperidine-4-carbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC(C=2C=CC=CC=2)(C#N)CC1 RQTVIKMRXYJTDX-UHFFFAOYSA-N 0.000 claims description 2
- IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 claims description 2
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 2
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 2
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 claims description 2
- ULCWZQJLFZEXCS-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-5-(2,2,2-trifluoroethoxy)oxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(OCC(F)(F)F)CCC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ULCWZQJLFZEXCS-UHFFFAOYSA-N 0.000 claims description 2
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N43/48—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09168284 | 2009-08-20 | ||
| EP09168284 | 2009-08-20 | ||
| PCT/EP2010/004844 WO2011020567A1 (de) | 2009-08-20 | 2010-08-07 | 3-triazolylphenyl-substituierte sulfid-derivate als akarizide und insektizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2468794T3 true ES2468794T3 (es) | 2014-06-17 |
Family
ID=41323636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10744515.7T Active ES2468794T3 (es) | 2009-08-20 | 2010-08-07 | Derivados de sulfuro sustituidos con 3-triazolilfenilo como acaricidas e insecticidas |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8722717B2 (Direct) |
| EP (1) | EP2467367B1 (Direct) |
| JP (1) | JP6140446B2 (Direct) |
| KR (1) | KR20120060217A (Direct) |
| CN (1) | CN102471291B (Direct) |
| BR (1) | BR112012003870B1 (Direct) |
| ES (1) | ES2468794T3 (Direct) |
| IN (1) | IN2012DN01531A (Direct) |
| MX (1) | MX2012001786A (Direct) |
| WO (1) | WO2011020567A1 (Direct) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005022147A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| AU2010272872B2 (en) * | 2009-07-16 | 2014-08-28 | Bayer Intellectual Property Gmbh | Synergistic active substance combinations containing phenyl triazoles |
| RU2012105122A (ru) * | 2009-07-16 | 2013-08-27 | Байер Кропсайенс Аг | Способ получения хиральных производных 3-триазолилсульфоксида |
| JP5736373B2 (ja) * | 2009-08-20 | 2015-06-17 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺ダニ剤及び殺虫剤として使用するための３−［１−（３−ハロアルキル）−トリアゾリル］−フェニル−スルフィド誘導体 |
| US9161542B2 (en) | 2011-05-26 | 2015-10-20 | Dow Agrosciences Llc | Pesticidal compositions and related methods |
| EP2604118A1 (en) * | 2011-12-15 | 2013-06-19 | Bayer CropScience AG | Active ingredient combinations having insecticidal and acaricidal properties |
| BR112014026358A2 (pt) * | 2012-04-27 | 2017-06-27 | Basf Se | composição pesticida, processo para a preparação da composição pesticida, utilização da composição pesticida, método para o controle das pragas de invertebrados, método para o tratamento e/ou para a proteção dos vegetais e método para a proteção do material de propagação do vegetal e/ou o vegetal |
| CN103493809A (zh) * | 2012-06-12 | 2014-01-08 | 永农生物科学有限公司 | 一种含有螺螨酯和环虫酰肼的复配农药组合物及其制剂 |
| CN102696651B (zh) * | 2012-06-12 | 2013-11-06 | 永农生物科学有限公司 | 一种含有螺螨酯的复配农药组合物及其制剂 |
| CN103493812A (zh) * | 2012-06-12 | 2014-01-08 | 永农生物科学有限公司 | 一种含有螺螨酯和三氟甲吡醚的复配农药组合物及其制剂 |
| CN102948419B (zh) * | 2012-11-06 | 2014-06-11 | 南京市白蚁防治研究所 | 一种杀白蚁药物复配组合 |
| CN103843795A (zh) * | 2012-12-07 | 2014-06-11 | 陕西美邦农药有限公司 | 一种含胺苯吡菌酮的杀菌组合物 |
| CN103858904A (zh) * | 2012-12-10 | 2014-06-18 | 陕西美邦农药有限公司 | 一种含胺苯吡菌酮的杀菌组合物 |
| CN103875696B (zh) * | 2012-12-24 | 2015-10-14 | 陕西汤普森生物科技有限公司 | 一种含胺苯吡菌酮的杀菌组合物 |
| WO2015036380A1 (de) * | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Verfahren zur reduktion von arylsulfoxiden zu arylthioethern |
| DE102014014266B3 (de) * | 2014-09-26 | 2015-08-27 | Skw Stickstoffwerke Piesteritz Gmbh | Verwendung von Pyrazol-Verbindungen als Mittel zur Verbesserung der Trockenstresstoleranz |
| CA2979549C (en) | 2015-03-27 | 2023-09-26 | Bayer Cropscience Lp | Methods and compositions for reducing fungal infestation and improving grass quality |
| CN105028437A (zh) * | 2015-09-09 | 2015-11-11 | 江苏省绿盾植保农药实验有限公司 | 一种含有三环唑和氟啶菌酯的杀菌剂 |
| ES2872003T3 (es) * | 2016-09-14 | 2021-11-02 | Janssen Pharmaceutica Nv | Inhibidores espirobicíclicos de la interacción de menina-MLL |
| CN111902043B (zh) | 2018-04-13 | 2023-05-16 | 拜耳公司 | 杀虫混合物的固体制剂 |
| MX2020010792A (es) * | 2018-04-13 | 2020-10-28 | Bayer Ag | Combinaciones de ingredientes activos con propiedades insecticidas, fungicidas y acaricidas. |
| CN109762016B (zh) * | 2019-02-22 | 2021-03-16 | 成都欣科医药有限公司 | 一种具有抗肿瘤活性的炔基膦酸双芳基锡配合物及其应用 |
| CN112724092B (zh) * | 2019-10-28 | 2022-04-01 | 山东康乔生物科技有限公司 | 一种芳基硫化物衍生物及其合成方法和应用 |
| IL293965A (en) | 2019-12-19 | 2022-08-01 | Janssen Pharmaceutica Nv | History of Spiro straight chain transformed |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7528974A (en) * | 1973-11-13 | 1976-06-10 | Commonwealth Scientific And Industrial Research Organization | Triazoles |
| DE3869167D1 (de) * | 1987-03-27 | 1992-04-23 | Kumiai Chemical Industry Co | Phenyltriazol-derivate und insectizid. |
| JPH01230562A (ja) * | 1987-03-27 | 1989-09-14 | Kumiai Chem Ind Co Ltd | フェニルトリアゾール誘導体及び殺虫剤 |
| WO1992000964A1 (fr) | 1990-07-05 | 1992-01-23 | Nippon Soda Co., Ltd. | Derive d'amine |
| JP3720131B2 (ja) * | 1995-08-15 | 2005-11-24 | 富士写真フイルム株式会社 | 熱現像感光材料 |
| AR005142A1 (es) * | 1995-12-21 | 1999-04-14 | Sumitomo Chemical Co | Derivados de triazol y su utilizacion |
| AU3536699A (en) | 1998-04-27 | 1999-11-16 | Ihara Chemical Industry Co. Ltd. | 3-arylphenyl sulfide derivatives and insecticides and miticides |
| JP4407062B2 (ja) * | 2001-02-14 | 2010-02-03 | 宇部興産株式会社 | ジフェニルジスルフィド誘導体の製造法 |
| UA79404C2 (en) | 2003-10-02 | 2007-06-11 | Basf Ag | 2-cyanobenzenesulfonamide for controlling pests |
| MX281941B (en) | 2004-02-18 | 2010-12-10 | Ishihara Sangyo Kaisha | Anthranilamide compounds, process for their production and pesticides containing them |
| NZ553200A (en) | 2004-10-20 | 2009-09-25 | Kumiai Chemical Industry Co | 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient |
| WO2006056433A2 (en) | 2004-11-26 | 2006-06-01 | Basf Aktiengesellschaft | Novel 2-cyano-3-(halo)alkoxy-benzenesulfonamide compounds for combating animal pests |
| DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
| DE602006019560D1 (de) | 2005-03-24 | 2011-02-24 | Basf Se | 2-cyanobenzolsulfonamidverbindungen zur behandlung von samen |
| US7491738B2 (en) | 2005-06-01 | 2009-02-17 | Meiji Seika Kaisha, Ltd. | Pest control agents |
| TWI388282B (zh) | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | 害蟲控制劑 |
| DK1937664T3 (da) | 2005-10-14 | 2011-07-18 | Sumitomo Chemical Co | Hydrazidforbindelse og pesticid anvendelse af den samme |
| US20090069317A1 (en) | 2005-11-21 | 2009-03-12 | Basf Se | Insecticidal Methods Using 3-Amino-1,2-Benzisothiazole Derivatives |
| TWI398433B (zh) | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺 |
| DE102006015470A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| DE102006015468A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| JP2007284356A (ja) * | 2006-04-12 | 2007-11-01 | Kumiai Chem Ind Co Ltd | ３−トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する農園芸用殺虫・殺ダニ・殺線虫剤 |
| JP2007284386A (ja) * | 2006-04-18 | 2007-11-01 | Kumiai Chem Ind Co Ltd | ３−ピラゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 |
| JP2007284387A (ja) * | 2006-04-18 | 2007-11-01 | Kumiai Chem Ind Co Ltd | ３−ピラゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 |
| TWI381811B (zh) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
| DE102006057036A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
| EA200901143A1 (ru) | 2007-03-01 | 2010-04-30 | Басф Се | Пестицидные активные смеси, включающие аминотиазолиновые соединения |
| US8802713B2 (en) | 2007-10-18 | 2014-08-12 | Kumiai Chemical Industry Co., Ltd. | 3-alkoxy-1-phenylpyrazole derivatives and pesticides |
| WO2009069312A1 (ja) * | 2007-11-30 | 2009-06-04 | Ihara Chemical Industry Co., Ltd. | （１ｈ－１，２，４－トリアゾール－１－イル）アリール化合物及びその製造方法 |
| CN101910139B (zh) * | 2008-01-10 | 2012-09-26 | 北兴化学工业株式会社 | 苯基三唑啉酮类的制造方法 |
| WO2009135613A1 (de) | 2008-05-07 | 2009-11-12 | Bayer Cropscience Aktiengesellschaft | Synergistische wirkstoffkombinationen |
| EP2269455A1 (en) | 2009-06-24 | 2011-01-05 | Bayer CropScience AG | Combinations of biological control agents and insecticides |
| EP2274982A1 (de) | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| RU2012105122A (ru) | 2009-07-16 | 2013-08-27 | Байер Кропсайенс Аг | Способ получения хиральных производных 3-триазолилсульфоксида |
| AU2010272872B2 (en) | 2009-07-16 | 2014-08-28 | Bayer Intellectual Property Gmbh | Synergistic active substance combinations containing phenyl triazoles |
| JP5736373B2 (ja) | 2009-08-20 | 2015-06-17 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺ダニ剤及び殺虫剤として使用するための３−［１−（３−ハロアルキル）−トリアゾリル］−フェニル−スルフィド誘導体 |
-
2010
- 2010-08-07 ES ES10744515.7T patent/ES2468794T3/es active Active
- 2010-08-07 WO PCT/EP2010/004844 patent/WO2011020567A1/de not_active Ceased
- 2010-08-07 KR KR1020127007100A patent/KR20120060217A/ko not_active Withdrawn
- 2010-08-07 BR BR112012003870-2A patent/BR112012003870B1/pt not_active IP Right Cessation
- 2010-08-07 JP JP2012525069A patent/JP6140446B2/ja not_active Expired - Fee Related
- 2010-08-07 CN CN201080036655.4A patent/CN102471291B/zh not_active Expired - Fee Related
- 2010-08-07 EP EP10744515.7A patent/EP2467367B1/de not_active Not-in-force
- 2010-08-07 MX MX2012001786A patent/MX2012001786A/es not_active Application Discontinuation
- 2010-08-07 IN IN1531DEN2012 patent/IN2012DN01531A/en unknown
- 2010-08-19 US US12/859,350 patent/US8722717B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012003870A2 (pt) | 2015-09-08 |
| US8722717B2 (en) | 2014-05-13 |
| JP6140446B2 (ja) | 2017-05-31 |
| MX2012001786A (es) | 2012-02-29 |
| JP2013502387A (ja) | 2013-01-24 |
| WO2011020567A1 (de) | 2011-02-24 |
| KR20120060217A (ko) | 2012-06-11 |
| EP2467367A1 (de) | 2012-06-27 |
| BR112012003870B1 (pt) | 2018-11-21 |
| CN102471291B (zh) | 2015-04-22 |
| EP2467367B1 (de) | 2014-04-09 |
| US20110046194A1 (en) | 2011-02-24 |
| CN102471291A (zh) | 2012-05-23 |
| IN2012DN01531A (Direct) | 2015-06-05 |
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