WO2024007862A1 - Para-substituted biphenyl thioether compound, composition, and use thereof - Google Patents
Para-substituted biphenyl thioether compound, composition, and use thereof Download PDFInfo
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- WO2024007862A1 WO2024007862A1 PCT/CN2023/101703 CN2023101703W WO2024007862A1 WO 2024007862 A1 WO2024007862 A1 WO 2024007862A1 CN 2023101703 W CN2023101703 W CN 2023101703W WO 2024007862 A1 WO2024007862 A1 WO 2024007862A1
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- WIPO (PCT)
- Prior art keywords
- para
- formula
- diphenyl sulfide
- buo
- substituted diphenyl
- Prior art date
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- -1 biphenyl thioether compound Chemical class 0.000 title claims abstract description 102
- 239000000203 mixture Chemical class 0.000 title claims abstract description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title abstract description 5
- 235000010290 biphenyl Nutrition 0.000 title abstract description 4
- 239000004305 biphenyl Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 20
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 15
- 241000607479 Yersinia pestis Species 0.000 claims description 32
- 241000238876 Acari Species 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 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 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- 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 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- 239000002917 insecticide Substances 0.000 description 28
- 239000000575 pesticide Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 241000238631 Hexapoda Species 0.000 description 15
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 12
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- 239000000126 substance Substances 0.000 description 12
- 241001454295 Tetranychidae Species 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 229950001664 phoxim Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 5
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 5
- 229960001259 diclofenac Drugs 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- VQZAADXKTFOEKP-UHFFFAOYSA-N 1-fluoro-2-iodo-5-methyl-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound CC1=CC(F)=C(I)C=C1SCC(F)(F)F VQZAADXKTFOEKP-UHFFFAOYSA-N 0.000 description 4
- 239000005946 Cypermethrin Substances 0.000 description 4
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 239000005951 Methiocarb Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- GDZNYEZGJAFIKA-UHFFFAOYSA-N acetoprole Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052956 cinnabar Inorganic materials 0.000 description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 4
- 229960005424 cypermethrin Drugs 0.000 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 description 4
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- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
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- 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 description 3
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
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- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 125000004862 thiobutyl group Chemical group 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
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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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
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- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
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- C07C317/00—Sulfones; Sulfoxides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the invention belongs to the technical field of pesticides, and specifically relates to a para-substituted diphenyl sulfide compound and composition, and the use of these compounds or their acceptable salts as pesticides and compositions as insecticides or acaricides. .
- Trifluoroethyl sulfide (sulfoxide) compounds are a new class of compounds with good acaricidal activity.
- Japan Combinatorial Chemical developed the first commercial trifluoroethyl sulfide compound, Flupentiofenox, which has a good control effect against two-spotted spider mites. Since then, it has triggered a research and development boom in this field.
- the chemical structural formula of Flupentiofenox is as follows:
- R 1 is selected from nitro, cyano, C 1 -C 4 alkylthio, trifluoromethanesulfonyl or SCH 2 CF 3 ;
- R 2 is selected from halogen, cyano or C 1 -C 4 alkyl;
- n choose from 0, 1 or 2.
- the present invention provides a para-substituted diphenyl sulfide compound and its synthesis method and application to solve the above technical problems.
- the inventors synthesized various aryl sulfide derivatives and conducted in-depth studies on their biological activities. It was found that the para-substituted diphenyl sulfide compounds represented by the following general formula are effective against various harmful organisms, especially against spider mites such as spider mites, two-spotted spider mites, Kanzawa spider mites, and Panonychus citrus mites. As the representative spider mites showed excellent control effects, research was continued and the present invention was completed.
- R 1 is selected from H, CN, halogen, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;
- n is selected from an integer from 0 to 2.
- R 1 is selected from H, CN, halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;
- n is selected from an integer from 0 to 2.
- R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3.
- n 0 or 1.
- R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3.
- R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, n-PrO, i-PrO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
- R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, cyclopropyl;
- n 0 or 1.
- the present invention also discloses an insecticidal or acaricidal composition, comprising an insecticidal or acaricidal effective amount of at least one of the above-mentioned para-substituted diphenyl sulfide compounds;
- preparation carriers or preparation auxiliaries are also included.
- the present invention also discloses a method for preventing and controlling pests or mites, which includes adding an effective amount of insecticidal or acaricidal at least one of the above-mentioned para-substituted diphenyl sulfide compounds or the above-mentioned insecticidal compound.
- Pesticide or acaricidal compositions are used on pests or mites and/or their habitats.
- the present invention also discloses the use of at least one of the para-substituted diphenyl sulfide compounds as described above or the insecticidal or acaricidal composition as described above in controlling pests or mites in agriculture and other fields. .
- Halogen or halogen refers to fluorine, chlorine, bromine, and iodine.
- C 1 -C 6 alkyl linear or branched chain alkyl with 1-6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or n-butyl, isobutyl, sec-butyl, tert-butyl et al.
- Halogenated C 1 -C 6 alkyl group a linear or branched chain alkyl group with 1 to 6 carbon atoms.
- the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen, for example, chloromethyl, dimethyl Chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
- C 1 -C 6 alkoxy a linear or branched chain alkyl group with 1 to 6 carbon atoms, connected to the structure through an oxygen atom bond.
- Halogenated C 1 -C 6 alkoxy linear or branched chain alkoxy with 1-6 carbon atoms.
- the hydrogen atoms on these alkoxy groups can be partially or completely replaced by halogen, for example, methyl chloride Oxygen, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
- the synthesis method of the compound described in formula I is specifically to pass the compound of formula VIII through the compound of formula VII, VI, V, IV, III (in the chemical formulas listed below, unless otherwise defined, the substituents and symbols are the same as those defined in formula I The substituents and symbols have the same meaning) to prepare a compound of formula II, and then prepare the target product compound of formula I from the compound of formula II.
- the compound of formula I can be prepared through an oxidation step to prepare the compound I'.
- reaction can be carried out under normal pressure or high pressure, preferably under atmospheric pressure, and post-treatment can be carried out according to conventional methods.
- the active compound of formula (I) of the present invention is suitable for controlling pests or mites, that is, controlling pests or mites, which refers to harmful or unwanted insects or mites, especially in agriculture, forestry, Harmful or unwanted insects or mites encountered in the field of storage protection and material protection as well as hygiene.
- the compounds of the invention are active against both generally sensitive and resistant species and are effective in all areas where the pest or mite develops. It is effective at all stages; the present invention also relates to a method for controlling pests or harmful mites, which method includes using a biologically effective amount of formula on the insect location, insect habitat, pest habitat, claimed area, or directly on the insects to be controlled.
- Compounds The compounds of the present invention may also be used to control other invertebrate pests or organisms.
- the insect habitat, pest habitat or pest mite habitat refers to the environment where insects, pests or pest mites live or where their eggs exist, including the air around them, food eaten or objects they come into contact with.
- insects, pests or pest mites live or where their eggs exist, including the air around them, food eaten or objects they come into contact with.
- the active compound for example, by applying the active compound to the seeds of the plant (before planting), to the seedlings, or planted cuttings, leaves, stems, fruits, grains and/or roots, or to the soil or other growing medium (before the crop is planted). before or after), by controlling insects or pest mites that eat, damage or come into contact with edible produce, ornamental plants, turf, pasture plants or other plants of economic value, and by controlling sap-feeding pests such as mealybugs and planthoppers , aphids, aphids, etc.
- insects or harmful mites such as two-spotted spider mites, cinnabar spider mites, etc. to protect these plants against diseases caused by viruses, fungi or bacteria; the plants include plants reproduced by conventional methods, and also include plants obtained by modern biological methods. Technologically modified genes to produce plants with insect or pest mite resistance, herbicide resistance, high yields and/or other beneficial characteristics. It is contemplated that these compounds may be useful in protecting fabrics, paper, stored grains, seeds and other foodstuffs, houses, buildings and the like, and/or places by applying the compounds of the present invention to or near these objects.
- Preventing and controlling pests or harmful mites, controlling pests or harmful mites, and suppressing pests or harmful mites all refer to reducing the number of viable insects, pests or harmful mites, or reducing the number of eggs of viable insects, pests or harmful mites .
- the degree of reduction achieved by a compound depends on the compound application rate, the specific compound used and the target insect, pest or mite species, at least in amounts that produce an effect.
- insects or other pests and mites that can be suppressed include, but are not limited to:
- Lepidoptera Heliothis spp., Helicoverpa spp., Spodoptera spp., Mythimna unipuncta, Agrotis ipsilon, Earias spp. .), Trichoplusia ni, Anticarsia gemmatalis, Rachiplusia nu, Plutella xylostella, Chilo spp, Scirpophaga incertulas), Sesamia inferens, Cnaphalocrocis medalis, Ostrinia nubilalis, Cydia pomonella, Carposina niponensis, Adoxophyes orana ), Archips argyrospilus, Pandemis heparana, Epinotia aporema, Eupoecilia ambiguella, Lobesia botrana, Polychrosis biteana , Pectinophora gossypiella, Pierisrapae, Phyll
- Coleoptera Diabrotica spp., Leptinotarsadecemlineata, Oulema oryzae, Anthonomusgrandis, Lissorhoptrus oryzophilus, Agriotesspp. ), Melanotus communis, Popillia japonica, Cyclocephala spp., Tribolium spp.;
- Homoptera Aphis spp., Myzus Persicae, Rhopalosiphumspp., Dysaphis plantaginea, Toxoptera spp., Alfalfa aphid (Aphis craccivora Koch), Euphorbia longum Macrosiphum euphorbiae, Aulacorthum solani, Sitobion avenae, Metopolophium dirhodum, Schizaphis graminum, Sitobion aphid Brachycolus noxius), black-tailed leafhopper (Nephotettix spp.), brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), gray planthopper (Laodelphax striatellus), whitefly (Bemisiatabaci), greenhouse whitefly (Trialeurodes vaporariorum) ), Aleurodes proletella, Aleurothrixus floccosus, Quad
- Hemiptera Lygus spp., Eurygaster maura, Nezaraviridula, Piezodorus guildingi, Leptocorisa varicornis, temperate bedbug (Cimex lectularius), tropical bedbug (Cimex hemipterus);
- Thysanoptera Frankliniella occidentalis, Thrips spp., Scirtothrips dorsalis;
- Isoptera Reticulitermes flavipes, Coptotermesformosanus, Reticulitermes virginicus, Heterotermesaureus, Reticulitermes hesperus, Coptotermes frenchii, Shedorhinotermes spp., Reticulitermes santonensis), Reticulitermes grassei, Reticulitermes banyulensis, Reticulitermes speratus, Reticulitermes hageni, Reticulitermes tibialis, Zootermopsis spp., Incisitermes spp., Marginal termite (Marginitermes spp.), Macrotermesspp., Microcerotermes spp., Microtermes spp.;
- Diptera Liriomyza spp., Musca domestica, Aedes spp., Culex spp., Anopheles spp., Fannia spp. ), waste fly (Stomoxys spp.);
- Hymenoptera Red ants (Iridomyrmex humilis), fire ants (Solenopsis spp.), Pharaoh ants (Monomorium pharaonis), Atta spp., harvest ants (Pogonomyrmex spp.), Camponotus spp., house ants ( Monomorium spp.), Tapinoma sessile, Tetramorium spp., Xylocapa spp., Vespula spp., Polistes spp.;
- Orthoptera locusts, crickets: black locust (Melanoplus spp.), East Asian migratory locust (Locustamigratoria), desert locust (Schistocerca gregaria), mole cricket (Gryllotalpidae) (mole crickets);
- Fleas (Ctenophalides spp.), Human Fleas (Pulex irritans);
- Acaridae including Tetranychidae, Eupodidae, Eriophyiade, Phytoseiidae, Acaridae, including but not limited to Tetranychus spp .), spider mite (Panonychus spp.), cinnabar spider mite (Tetranychus cinnabarinus), Oriental spider mite (Eotetranychus carpini), two-spotted spider mite (Tetranychus urticae Koch.), citrus rust mite (Phyllocoptruta oleivora), Aculus pelekassi, Brevipalpus phoenicis, Boophilus spp., Dermacentor variabilis, Rhipicephalussanguineus, Amblyomma americanum, Ixodes spp., Cat dorsal anus Mites (Notoedres cati), scabies (Sarcoptes scabiei), dust mites (
- Class Nematoda Dirofilaria immitis, Meloidogyne spp., Heterodera spp., Hoplolaimus columbus, Belonolaimus spp., root rot Nematodes (Pratylenchus spp.), kidney-shaped nematodes (Rotylenchus reniformis), decorative small ring nematodes (Criconemellaornata), stem nematodes (Ditylenchus spp.), leaf bud nematodes (Aphelenchoides besseyi), rice field hidden root nematodes (Hirschmanniella spp.).
- the compound represented by formula I of the present invention When used at low concentrations, the compound represented by formula I of the present invention also shows excellent control effects against various pests or pest mites. Both pupae and adults have insecticidal or acaricidal activity. The compound of formula I of the present invention also shows excellent control activity against those pests or mites that have developed resistance to traditional insecticides or acaricides.
- the compounds of formula I can be formulated in a variety of ways, depending on the usual biological and/or chemical physical parameters.
- Suitable formulation options are: wettable powder (WP), wettable liquid (SL), soluble powder (SP), dispersible liquid (DC), aqueous (AS), microemulsion (ME), emulsifiable concentrate (EC), water emulsion (EW), sprayable solution, suspension concentrate (SC), dispersible oil suspension (OD), powder (DP), microencapsulated suspension (CS), water-dispersible granule (WG), water-soluble granules (SG), large granules (GG), granules for broadcast and soil application (GR), aerosols (AE), ultra-low volumes (ULV) and wax products.
- Necessary formulation auxiliaries such as inert substances, surfactants, solvents and other additives.
- suitable active substances that can be mixed with the active substances of the present invention are, for example, those known in "Pesticide Handbook" (Beijing: Chemical Industry Press, 1st Edition, May 2015) substance.
- the insecticidal active substances mentioned below can be combined with Mixture of compounds of formula I (note: the name of the compound is either a common name according to the International Organization for Standardization (ISO) or a chemical name, with a code name when appropriate): antibiotic insecticides (e.g., alobactin ( allosamidin) and thuringin); macrolide insecticides (e.g., spinosyn, spinetoram, and other spinosyns including 21-butylspinetoram and their derivatives); Malawitin Bacteriocin pesticides such as abamectin, doramectin, emamectin, eplenomectin, ivermectin and selamectin;
- B. thuringiensis subsp. aizawai B. thuringiensis kurstaki subspecies (B. thuringiensis subsp.kurstaki), B.thuringiensis subsp.tenebrionis, Beauveria bassiana, Cydia pomomella granulosis virus, Spodoptera litura nuclear polyhedrosis virus ( NPV) (Douglas fir tussock moth NPV), gypsy mothNPV (gypsy mothNPV), Helicoverpa zea MPV (Helicoverpa zea MPV), Indian meal moth granulosis virus (India meal moth granulosis virus), Metarhizium anisopliae (Metarhiziumanisopliae) , Nosema locustae, Paecilomyces fumosoroseus, P.lilacinus, Photorhabdus luminesc
- Some of the fungicides that can be used in combination with the compounds of the present invention include: 2-(cyanothiomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, leucospora, quisqualis ), oxyconazole, azoxystrobin, Bacillus subtilis, benoxyl, benomyl, benthiazole, benzylinobenzene-sulfonate (BABS) salt, bicarbonate, biphenyl, phytonzolin, Diphenyltriazole, gray blastin, borax, Bordeaux mixture, boscalid, furfuroconazole, pyrimethonol sulfonate, lime sulfur mixture, captafant, captan, carbendazim, phosphine Spirit, cycloprofen, carvone, Dimaosan (Chloroneb), chlorothalonil, ethanol, Copper hydroxide, copper octoate, copper
- Suspension agent Weigh 20% of the compound of formula (I), 2% FS3000 (phosphate anionic surfactant), 3% NS-500LQ (nonionic hydroxyl polyethylene oxide block copolymer), 0.5% xanthan gum, 1.5% magnesium aluminum silicate, 5% ethylene glycol, 0.5% organically modified silicone defoaming agent, deionized water was added to 100% to make a slurry, and the product was obtained after sanding .
- Emulsifiable concentrate Weigh 25% of the compound of formula (I), 15% cyclohexanone, 8% emulsifier, 20% DMF, add xylene to 100%, and obtain the product after being sheared by a high-shear emulsifying machine.
- Wettable powder Weigh 40% of the compound of formula (I), 7% sodium dodecylbenzene sulfonate, 10% sodium lignin sulfonate, and the rest is kaolin, and obtain the product after airflow pulverization.
- a solution containing 0.1% Tween 80 is used to prepare a test solution of the required concentration and is ready for use. Take pea seedlings at the two-leaf stage, inoculate them with spider mites and investigate the base number. Use a spray tower to spray the entire plant. Each treatment is repeated three times. After treatment, they are placed in a standard observation room. After 72 hours, the number of surviving mites is investigated and the mortality rate is calculated. .
- Compounds with target mortality rates above 80% include: compounds 1-10, 12-16, 18-24, 26, 31-33, 36, and CK1, 8, 9, and 10 among the control compounds CK1-15.
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Abstract
Provided are a para-substituted biphenyl thioether compound, a composition, and use thereof. The compound has a structure represented by formula (I): , the definitions of the groups in the formula are provided in the description. The para-substituted biphenyl thioether compound has superior insecticidal or acaricidal activity to known compounds and good safety for crops.
Description
本发明属于农药技术领域,具体涉及一种对位取代的联苯硫醚类化合物、组合物,并涉及这些化合物或其作为农药可接受的盐、组合物作为杀虫剂或杀螨剂的用途。The invention belongs to the technical field of pesticides, and specifically relates to a para-substituted diphenyl sulfide compound and composition, and the use of these compounds or their acceptable salts as pesticides and compositions as insecticides or acaricides. .
三氟乙基硫醚(亚砜)类化合物是一类杀螨活性良好的新型化合物。2020年日本组合化学开发了第一个商品化三氟乙基硫醚类化合物,Flupentiofenox,对二斑叶螨具有很好的防效,自此引起了对该领域的研发热潮。Flupentiofenox的化学结构式如下所示:
Trifluoroethyl sulfide (sulfoxide) compounds are a new class of compounds with good acaricidal activity. In 2020, Japan Combinatorial Chemical developed the first commercial trifluoroethyl sulfide compound, Flupentiofenox, which has a good control effect against two-spotted spider mites. Since then, it has triggered a research and development boom in this field. The chemical structural formula of Flupentiofenox is as follows:
Trifluoroethyl sulfide (sulfoxide) compounds are a new class of compounds with good acaricidal activity. In 2020, Japan Combinatorial Chemical developed the first commercial trifluoroethyl sulfide compound, Flupentiofenox, which has a good control effect against two-spotted spider mites. Since then, it has triggered a research and development boom in this field. The chemical structural formula of Flupentiofenox is as follows:
沈阳中化农药化工研发有限公司于专利CN113943238A中公布的如下通式化合物具有杀螨活性:
The following general formula compound published by Shenyang Sinochem Pesticide Chemical R&D Co., Ltd. in patent CN113943238A has acaricidal activity:
The following general formula compound published by Shenyang Sinochem Pesticide Chemical R&D Co., Ltd. in patent CN113943238A has acaricidal activity:
其中,R1选自硝基、氰基、C1-C4烷硫基、三氟甲磺酰基或SCH2CF3;R2选自卤素、氰基或C1-C4烷基;n选自0、1或2。Among them, R 1 is selected from nitro, cyano, C 1 -C 4 alkylthio, trifluoromethanesulfonyl or SCH 2 CF 3 ; R 2 is selected from halogen, cyano or C 1 -C 4 alkyl; n Choose from 0, 1 or 2.
沈阳中化农药化工研发有限公司于专利WO2017067500中公布的如下化合物具有很好的杀螨活性:
The following compounds published by Shenyang Sinochem Pesticide Chemical R&D Co., Ltd. in patent WO2017067500 have good acaricidal activity:
The following compounds published by Shenyang Sinochem Pesticide Chemical R&D Co., Ltd. in patent WO2017067500 have good acaricidal activity:
已知以上所提及的文献中所记载的活性化合物在有害动物特别是螨虫防治时仍然具有较低的杀灭活性,但是其在低浓度下其杀螨活性往往不能令人满意,并且对获得了抗药性的叶螨类防治效果更差,因此农业生产中仍然急需高效低毒,对抗性螨虫具有优良杀灭效果的新药。It is known that the active compounds recorded in the above-mentioned documents still have low killing activity when controlling harmful animals, especially mites. However, their miticidal activity is often unsatisfactory at low concentrations and is not effective in obtaining The control effect of resistant spider mites is even worse. Therefore, there is still an urgent need in agricultural production for new drugs with high efficiency, low toxicity and excellent killing effect against resistant mites.
发明内容Contents of the invention
针对现有技术中螨虫防治的药剂杀灭活性不足,本发明提供一种对位取代的联苯硫醚类化合物及其合成方法和应用,以解决上述技术问题。为了开发具有上述理想特性的有害生物防治剂,发明人合成了各种芳基硫化物衍生物并对其生物活性进行了深入研究。结果发现,下述通式表示的对位取代的联苯硫醚类化合物对各种有害生物,特别是对以朱砂叶螨、二斑叶螨、神泽氏叶螨﹑柑桔全爪螨等为代表的叶螨类显示出卓越的防治效果,继续进行研究并完成了本发明。In view of the insufficient killing activity of mite control agents in the prior art, the present invention provides a para-substituted diphenyl sulfide compound and its synthesis method and application to solve the above technical problems. In order to develop pest control agents with the above-mentioned desirable properties, the inventors synthesized various aryl sulfide derivatives and conducted in-depth studies on their biological activities. It was found that the para-substituted diphenyl sulfide compounds represented by the following general formula are effective against various harmful organisms, especially against spider mites such as spider mites, two-spotted spider mites, Kanzawa spider mites, and Panonychus citrus mites. As the representative spider mites showed excellent control effects, research was continued and the present invention was completed.
本发明为实现上述目的采用的技术方案是:一种对位取代的联苯硫醚类化合物,其结构式如式(I)所示:
The technical solution adopted by the present invention to achieve the above object is: a para-substituted diphenyl sulfide compound, the structural formula of which is as shown in formula (I):
The technical solution adopted by the present invention to achieve the above object is: a para-substituted diphenyl sulfide compound, the structural formula of which is as shown in formula (I):
式(I)中,In formula (I),
R1选自H、CN、卤素、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6烷氧基、卤代C1-C6烷氧基、C3-C6环烷基、C3-C6环氧烷基或C3-C6环烷基氧基;R 1 is selected from H, CN, halogen, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;
n选自0-2的整数。n is selected from an integer from 0 to 2.
进一步地,式(I)中,Further, in formula (I),
R1选自H、CN、卤素、C1-C4烷基、卤代C1-C4烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C6环烷基、C3-C6环氧烷基或C3-C6环烷基氧基;R 1 is selected from H, CN, halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;
n选自0-2的整数。n is selected from an integer from 0 to 2.
进一步地,式(I)中,Further, in formula (I),
R1选自H、CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、CCl3、CHCl2、CH2Cl、CBr3、CH2Br、CHBr2、CH2CF3、CH2CFH2、CH2CHF2、乙烯基、乙炔基、MeO、EtO、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基;R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3. CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CH 2 Br , CHBr 2 , CH 2 CF 3 , CH 2 CFH 2 , CH 2 CHF 2 , vinyl, ethynyl, MeO, EtO, n-PrO , i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexaneoxy base;
n为0或1。n is 0 or 1.
进一步地,式(I)中,Further, in formula (I),
R1选自H、CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、CCl3、CHCl2、CH2Cl、CBr3、CH2Br、CHBr2、CH2CF3、MeO、EtO、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基。R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3. CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CH 2 Br, CHBr 2 , CH 2 CF 3 , MeO, EtO, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO , t-BuO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
进一步地,式(I)中,Further, in formula (I),
R1选自CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、MeO、EtO、n-PrO、i-PrO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基。R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, n-PrO, i-PrO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
进一步地,式(I)中,Further, in formula (I),
R1选自CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、MeO、EtO、环丙烷基;R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, cyclopropyl;
n为0或1。n is 0 or 1.
进一步地,式(I)结构化合物选自:
Further, the compound of formula (I) is selected from:
Further, the compound of formula (I) is selected from:
本发明还公开了一种杀虫或杀螨组合物,包括杀虫或杀螨有效量的如上所述的对位取代的联苯硫醚类化合物中的至少一种;The present invention also discloses an insecticidal or acaricidal composition, comprising an insecticidal or acaricidal effective amount of at least one of the above-mentioned para-substituted diphenyl sulfide compounds;
进一步地,还包括制剂载体或制剂助剂。Furthermore, preparation carriers or preparation auxiliaries are also included.
本发明还公开了一种防治害虫或害螨的方法,包括将杀虫或杀螨有效量的如上所述的对位取代的联苯硫醚类化合物中的至少一种或如上所述的杀虫或杀螨组合物使用在害虫或害螨和/或其栖息地上。The present invention also discloses a method for preventing and controlling pests or mites, which includes adding an effective amount of insecticidal or acaricidal at least one of the above-mentioned para-substituted diphenyl sulfide compounds or the above-mentioned insecticidal compound. Pesticide or acaricidal compositions are used on pests or mites and/or their habitats.
本发明还公开了如上所述的对位取代的联苯硫醚类化合物中的至少一种或如上所述的杀虫或杀螨组合物在农业和其它领域中控制害虫或害螨上的用途。The present invention also discloses the use of at least one of the para-substituted diphenyl sulfide compounds as described above or the insecticidal or acaricidal composition as described above in controlling pests or mites in agriculture and other fields. .
在上述化合物结构式的定义中,所使用的专业术语均具有如下含义:In the definition of the above compound structural formula, the professional terms used have the following meanings:
卤或卤素:指氟、氯、溴、碘。Halogen or halogen: refers to fluorine, chlorine, bromine, and iodine.
C1-C6烷基:碳原子数为1-6的直链或支链烷基,例如甲基、乙基、丙基、异丙基或正丁基、异丁基、仲丁基、叔丁基等。C 1 -C 6 alkyl: linear or branched chain alkyl with 1-6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or n-butyl, isobutyl, sec-butyl, tert-butyl et al.
卤代C1-C6烷基:碳原子数为1-6的直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤素所取代,例如,氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。Halogenated C 1 -C 6 alkyl group: a linear or branched chain alkyl group with 1 to 6 carbon atoms. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen, for example, chloromethyl, dimethyl Chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
C1-C6烷氧基:碳原子数为1-6的直链或支链烷基,经氧原子键连接到结构上。C 1 -C 6 alkoxy: a linear or branched chain alkyl group with 1 to 6 carbon atoms, connected to the structure through an oxygen atom bond.
卤代C1-C6烷氧基:碳原子数为1-6的直链或支链烷氧基,在这些烷氧基上的氢原子可部分或全部被卤素所取代,例如,氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。Halogenated C 1 -C 6 alkoxy: linear or branched chain alkoxy with 1-6 carbon atoms. The hydrogen atoms on these alkoxy groups can be partially or completely replaced by halogen, for example, methyl chloride Oxygen, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
式I所述化合物的合成方法,具体是将式VIII化合物经由式VII、VI、V、IV、III化合物(在下列列举的化学式中,只要未另外进行定义,取代基和符号与式I中定义的取代基和符号具有相同的意义)制备得到式II化合物,再由式II化合物制备得到目标产物式I化合物,式I化合物可经过氧化步骤制备得到I’化合物。
The synthesis method of the compound described in formula I is specifically to pass the compound of formula VIII through the compound of formula VII, VI, V, IV, III (in the chemical formulas listed below, unless otherwise defined, the substituents and symbols are the same as those defined in formula I The substituents and symbols have the same meaning) to prepare a compound of formula II, and then prepare the target product compound of formula I from the compound of formula II. The compound of formula I can be prepared through an oxidation step to prepare the compound I'.
The synthesis method of the compound described in formula I is specifically to pass the compound of formula VIII through the compound of formula VII, VI, V, IV, III (in the chemical formulas listed below, unless otherwise defined, the substituents and symbols are the same as those defined in formula I The substituents and symbols have the same meaning) to prepare a compound of formula II, and then prepare the target product compound of formula I from the compound of formula II. The compound of formula I can be prepared through an oxidation step to prepare the compound I'.
进一步地,反应可以在常压或高压下进行,优选在大气压下进行,可根据常规方法进行后处理。Further, the reaction can be carried out under normal pressure or high pressure, preferably under atmospheric pressure, and post-treatment can be carried out according to conventional methods.
本发明式(I)活性化合物适于防治害虫或害螨,也即控制害虫或害螨,所述的害虫或害螨指的有害的或不想要的昆虫或螨类,尤其是农业、林业、储藏品保护和材料保护以及卫生领域所遇到的有害的或不想要的昆虫或螨类,本发明化合物对于一般敏感性和抗性物种都是有活性的,并且在害虫或害螨发育的所有阶段都有效;本发明还涉及抑制害虫或害螨的方法,该方法包括对昆虫所在地、昆虫栖息地、害虫栖息地、要求保护的面积、或直接在要控制的昆虫上使用生物有效量的式(I)化合物。本发明的化合物也可以用来控制其它无脊椎害虫或生物。The active compound of formula (I) of the present invention is suitable for controlling pests or mites, that is, controlling pests or mites, which refers to harmful or unwanted insects or mites, especially in agriculture, forestry, Harmful or unwanted insects or mites encountered in the field of storage protection and material protection as well as hygiene. The compounds of the invention are active against both generally sensitive and resistant species and are effective in all areas where the pest or mite develops. It is effective at all stages; the present invention also relates to a method for controlling pests or harmful mites, which method includes using a biologically effective amount of formula on the insect location, insect habitat, pest habitat, claimed area, or directly on the insects to be controlled. (I) Compounds. The compounds of the present invention may also be used to control other invertebrate pests or organisms.
所述的昆虫栖息地、害虫栖息地或害螨栖息地是指昆虫、害虫或害螨生活或它们的卵存在的环境,包括其周围的空气、食用的食物或接触的物体。例如,通过将活性化合物施用至植株的种子(在种植前)、至秧苗、或种植的插条、叶子、茎、果实、谷粒和/或根,或至土壤或其它生长介质(在作物种植前或之后),可以控制食用、毁坏或接触可食用农产品、观赏植物、草皮、牧草植物或其它具有经济价值的植物的昆虫或害螨,也可以通过控制食汁液的害虫如粉虱、飞虱、蚜虫和蚜虫等或害螨如二斑叶螨、朱砂叶螨等而达到保护这些植物抵抗病毒、真菌或细菌导致的疾病;所述植物包括通过常规方法繁殖得到的植物,也包括通过现代生物技术改变基因得到的具有昆虫或害螨抵抗力、除草剂抵抗力、高产量/或其它有益特性的植物。可以预期这些化合物能适用于保护织物、纸、储存的谷物、种子和其它食品、房屋、建筑物等物品和/或场所,通过将本发明的化合物施用到这些物体上或这些物体附近来实现。The insect habitat, pest habitat or pest mite habitat refers to the environment where insects, pests or pest mites live or where their eggs exist, including the air around them, food eaten or objects they come into contact with. For example, by applying the active compound to the seeds of the plant (before planting), to the seedlings, or planted cuttings, leaves, stems, fruits, grains and/or roots, or to the soil or other growing medium (before the crop is planted). before or after), by controlling insects or pest mites that eat, damage or come into contact with edible produce, ornamental plants, turf, pasture plants or other plants of economic value, and by controlling sap-feeding pests such as mealybugs and planthoppers , aphids, aphids, etc. or harmful mites such as two-spotted spider mites, cinnabar spider mites, etc. to protect these plants against diseases caused by viruses, fungi or bacteria; the plants include plants reproduced by conventional methods, and also include plants obtained by modern biological methods. Technologically modified genes to produce plants with insect or pest mite resistance, herbicide resistance, high yields and/or other beneficial characteristics. It is contemplated that these compounds may be useful in protecting fabrics, paper, stored grains, seeds and other foodstuffs, houses, buildings and the like, and/or places by applying the compounds of the present invention to or near these objects.
所说的防治害虫或害螨、控制害虫或害螨、抑制害虫或害螨,均指的是降低成活昆虫、害虫或害螨的数量,或降低可存活昆虫、害虫或害螨的卵的数量。化合物实现的降低程度取决于化合物的施用率、所用的特定化合物和目标昆虫、害虫或害螨物种,至少需使用能产生效果的量。
Preventing and controlling pests or harmful mites, controlling pests or harmful mites, and suppressing pests or harmful mites all refer to reducing the number of viable insects, pests or harmful mites, or reducing the number of eggs of viable insects, pests or harmful mites . The degree of reduction achieved by a compound depends on the compound application rate, the specific compound used and the target insect, pest or mite species, at least in amounts that produce an effect.
所说的“死亡率”是指足以使被处理的昆虫、害虫或害螨数量发生可测量性降低的量。通常,使用1至1000ppm(按重量计)的活性化合物。例如,可以抑制的昆虫或其它害虫、害螨包括,但不限于:By "mortality" we mean an amount sufficient to cause a measurable reduction in the number of insects, pests or mites being treated. Typically, 1 to 1000 ppm (by weight) of active compound is used. For example, insects or other pests and mites that can be suppressed include, but are not limited to:
鳞翅目:棉铃虫(Heliothis spp.)、棉铃虫(Helicoverpa spp.)、夜蛾(Spodoptera spp.)、秘夜蛾粘虫(Mythimna unipuncta)、小地老虎(Agrotis ipsilon)、金刚钻(Earias spp.)、粉纹夜蛾(Trichoplusia ni)、黎豆夜蛾(Anticarsia gemmatalis)、薄荷灰叶蛾(Rachiplusia nu)、小菜蛾(Plutella xylostella)、二化螟(Chilo spp)、三化螟(Scirpophaga incertulas)、大螟(Sesamia inferens)、稻纵卷叶螟(Cnaphalocrocis medinalis)、玉米螟(Ostrinia nubilalis)、苹果蠹蛾(Cydia pomonella)、桃小食心虫(Carposina niponensis)、棉褐带卷叶蛾(Adoxophyes orana)、果树黄卷蛾(Archips argyrospilus)、苹褐卷叶蛾(Pandemis heparana)、夜小卷蛾(Epinotia aporema)、葡萄与苹果卷叶蛾(Eupoecilia ambiguella)、葡萄花翅小卷蛾(Lobesia botrana)、Polychrosis biteana、棉红铃虫(Pectinophora gossypiella)、菜青虫(Pierisrapae)、Phyllonorycter spp.、旋纹潜蛾(Leucoptera malifoliella)、柑橘潜叶蛾(Phyllocnisitis citrella)、甜菜夜蛾(Podoptera exigua Hübner);Lepidoptera: Heliothis spp., Helicoverpa spp., Spodoptera spp., Mythimna unipuncta, Agrotis ipsilon, Earias spp. .), Trichoplusia ni, Anticarsia gemmatalis, Rachiplusia nu, Plutella xylostella, Chilo spp, Scirpophaga incertulas), Sesamia inferens, Cnaphalocrocis medalis, Ostrinia nubilalis, Cydia pomonella, Carposina niponensis, Adoxophyes orana ), Archips argyrospilus, Pandemis heparana, Epinotia aporema, Eupoecilia ambiguella, Lobesia botrana, Polychrosis biteana , Pectinophora gossypiella, Pierisrapae, Phyllonorycter spp., Leucoptera malifoliella, Phyllocnisitis citrella, Beet armyworm (Podoptera exigua Hübner);
鞘翅目:叶甲(Diabrotica spp.)、马铃薯叶甲(Leptinotarsadecemlineata)、稻负泥虫(Oulema oryzae)、棉铃象甲虫(Anthonomusgrandis)、稻水象甲(Lissorhoptrus oryzophilus)、金针虫叩甲(Agriotesspp.)、Melanotus communis、日本豆金龟子(Popillia japonica)、圆头犀金龟属种(Cyclocephala spp.)、拟谷盗(Tribolium spp.);Coleoptera: Diabrotica spp., Leptinotarsadecemlineata, Oulema oryzae, Anthonomusgrandis, Lissorhoptrus oryzophilus, Agriotesspp. ), Melanotus communis, Popillia japonica, Cyclocephala spp., Tribolium spp.;
同翅目:蚜虫(Aphis spp.)、烟蚜(Myzus Persicae)、Rhopalosiphumspp.、车前圆尾蚜(Dysaphis plantaginea)、桔蚜(Toxoptera spp.)、苜蓿蚜虫(Aphis craccivora Koch)、大戟长管蚜(Macrosiphum euphorbiae)、茄无网蚜(Aulacorthum solani)、麦长管蚜(Sitobion avenae)、麦无网长管蚜(Metopolophium dirhodum)、麦二叉蚜(Schizaphis graminum)、麦双尾蚜(Brachycolus noxius)、黑尾叶蝉(Nephotettix spp.)、褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatella furcifera)、灰飞虱(Laodelphax striatellus)、烟粉虱(Bemisiatabaci)、温室白粉虱(Trialeurodes vaporariorum)、Aleurodes proletella、丝绒粉虱(Aleurothrixus floccosus)、梨园蚧(Quadraspidiotusperniciosus)、矢尖蚧(Unaspis yanonenses)、红蜡蚧(Ceroplastes rubens)、红圆蚧(Aonidiella aurantii);Homoptera: Aphis spp., Myzus Persicae, Rhopalosiphumspp., Dysaphis plantaginea, Toxoptera spp., Alfalfa aphid (Aphis craccivora Koch), Euphorbia longum Macrosiphum euphorbiae, Aulacorthum solani, Sitobion avenae, Metopolophium dirhodum, Schizaphis graminum, Sitobion aphid Brachycolus noxius), black-tailed leafhopper (Nephotettix spp.), brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), gray planthopper (Laodelphax striatellus), whitefly (Bemisiatabaci), greenhouse whitefly (Trialeurodes vaporariorum) ), Aleurodes proletella, Aleurothrixus floccosus, Quadraspidiotusperniciosus, Unaspis yanonenses, Ceroplastes rubens, Aonidiella aurantii;
半翅目:盲蝽(Lygus spp.)、Eurygaster maura、稻绿蝽(Nezaraviridula)、Piezodorus guildingi、稻缘椿象(Leptocorisa varicornis)、温带臭虫(Cimex lectularius)、热带臭虫(Cimex hemipterus);Hemiptera: Lygus spp., Eurygaster maura, Nezaraviridula, Piezodorus guildingi, Leptocorisa varicornis, temperate bedbug (Cimex lectularius), tropical bedbug (Cimex hemipterus);
缨翅目:西花蓟马(Frankliniella occidentalis)、蓟马(Thrips spp.)、茶黄蓟马(Scirtothrips dorsalis);Thysanoptera: Frankliniella occidentalis, Thrips spp., Scirtothrips dorsalis;
等翅目:黄肢散白蚁(Reticulitermes flavipes)、家白蚁(Coptotermesformosanus)、南方散白蚁(Reticulitermes virginicus)、Heterotermesaureus、西方散白蚁(Reticulitermes hesperus)、Coptotermes frenchii、Shedorhinotermes spp.、桑特散白蚁(Reticulitermes santonensis)、Reticulitermes grassei、Reticulitermes banyulensis、黄胸散白蚁(Reticulitermes speratus)、Reticulitermes hageni、美黑胫散白蚁(Reticulitermes tibialis)、湿木白蚁(Zootermopsis spp.)、楹白蚁(Incisitermes spp.)、缘白蚁(Marginitermes spp.)、大白蚁(Macrotermesspp.)、大锯白蚁(Microcerotermes spp.)、蛮白蚁(Microtermes spp.);Isoptera: Reticulitermes flavipes, Coptotermesformosanus, Reticulitermes virginicus, Heterotermesaureus, Reticulitermes hesperus, Coptotermes frenchii, Shedorhinotermes spp., Reticulitermes santonensis), Reticulitermes grassei, Reticulitermes banyulensis, Reticulitermes speratus, Reticulitermes hageni, Reticulitermes tibialis, Zootermopsis spp., Incisitermes spp., Marginal termite (Marginitermes spp.), Macrotermesspp., Microcerotermes spp., Microtermes spp.;
双翅目:斑潜蝇(Liriomyza spp.)、家蝇(Musca domestica)、斑蚊(Aedes spp.)、家蚊(Culex spp.)、疟蚊(Anopheles spp.)、厕蝇(Fannia spp.)、废蝇(Stomoxys spp.);
Diptera: Liriomyza spp., Musca domestica, Aedes spp., Culex spp., Anopheles spp., Fannia spp. ), waste fly (Stomoxys spp.);
膜翅目:红蚁(Iridomyrmex humilis)、火蚁(Solenopsis spp.)、法老蚁(Monomorium pharaonis)、Atta spp.、收获蚁(Pogonomyrmexspp.)、弓背蚁(Camponotus spp.)、小家蚁(Monomorium spp.)、臭家蚁(Tapinoma sessile)、铺道蚁(Tetramorium spp.)、Xylocapa spp.、胡蜂(Vespula spp.)、长足胡蜂(Polistes spp.);Hymenoptera: Red ants (Iridomyrmex humilis), fire ants (Solenopsis spp.), Pharaoh ants (Monomorium pharaonis), Atta spp., harvest ants (Pogonomyrmex spp.), Camponotus spp., house ants ( Monomorium spp.), Tapinoma sessile, Tetramorium spp., Xylocapa spp., Vespula spp., Polistes spp.;
食毛目(羽虱(chewing lice));Chewing lice);
虱目(吸血虱(sucking lice)):耻阴虱(Pthirus pubis)、虱类(Pediculusspp.);Order Lice (sucking lice): Pthirus pubis, Pediculus spp.;
直翅目(蝗虫、蟋蟀):黑蝗(Melanoplus spp.)、东亚飞蝗(Locustamigratoria)、沙漠蝗(Schistocerca gregaria)、蝼蛄(Gryllotalpidae)(蝼蛄(mole crickets));Orthoptera (locusts, crickets): black locust (Melanoplus spp.), East Asian migratory locust (Locustamigratoria), desert locust (Schistocerca gregaria), mole cricket (Gryllotalpidae) (mole crickets);
蜚蠊目(蜚蠊(cockroaches)):东方蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、美洲大蠊(Periplaneta americana)、长须蜚蠊(Supella longipalpa)、澳洲蜚蠊(Periplaneta australasiae)、褐斑大蠊(Periplaneta brunnea)、宾夕法尼亚木蠊(Parcoblatta pennsylvanica)、黑胸大蠊(Periplaneta fuliginosa)、蔗蠊(Pycnoscelus surinamensis);Order Cockroaches: Blatta orientalis, Blattella germanica, Periplaneta americana, Supella longipalpa, Periplaneta australasiae , Periplaneta brunnea, Parcoblatta pennsylvanica, Periplaneta fuliginosa, Pycnoscelus surinamensis;
蚤目:跳蚤(Ctenophalides spp.)、人蚤(Pulex irritans);Order Flea: Fleas (Ctenophalides spp.), Human Fleas (Pulex irritans);
蜱螨目:包括叶螨科(Tetranychidae)、真足螨科(Eupodidae)、瘿螨科(Eriophyiade)、植绥螨科(Phytoseiidae)、粉螨科(Acaridae),具体包括但不限于叶螨(Tetranychus spp.)、蜘蛛螨(Panonychus spp.)、朱砂叶螨(Tetranychus cinnabarinus)、东方叶螨(Eotetranychus carpini)、二斑叶螨(Tetranychus urticae Koch.)、柑桔锈螨(Phyllocoptruta oleivora)、Aculus pelekassi、紫红短须螨(Brevipalpus phoenicis)、牛蜱(Boophilusspp.)、变异革蜱(Dermacentor variabilis)、血红扇头蜱(Rhipicephalussanguineus)、美洲花蜱(Amblyomma americanum)、真蜱(Ixodes spp.)、猫背肛螨(Notoedres cati)、疥螨(Sarcoptes scabiei)、尘螨(Dermatophagoides spp.);Acaridae: including Tetranychidae, Eupodidae, Eriophyiade, Phytoseiidae, Acaridae, including but not limited to Tetranychus spp .), spider mite (Panonychus spp.), cinnabar spider mite (Tetranychus cinnabarinus), Oriental spider mite (Eotetranychus carpini), two-spotted spider mite (Tetranychus urticae Koch.), citrus rust mite (Phyllocoptruta oleivora), Aculus pelekassi, Brevipalpus phoenicis, Boophilus spp., Dermacentor variabilis, Rhipicephalussanguineus, Amblyomma americanum, Ixodes spp., Cat dorsal anus Mites (Notoedres cati), scabies (Sarcoptes scabiei), dust mites (Dermatophagoides spp.);
线虫纲(Nematoda):犬恶丝虫(Dirofilaria immitis)、根结线虫(Meloidogyne spp.)、包囊线虫(Heterodera spp.)、冠线虫(Hoplolaimuscolumbus)、针刺线虫(Belonolaimus spp.)、根腐线虫(Pratylenchusspp.)、肾形线虫(Rotylenchus reniformis)、装饰小环线虫(Criconemellaornata)、茎线虫(Ditylenchus spp.)、叶芽线虫(Aphelenchoides besseyi)、稻田潜根线虫(Hirschmanniella spp.)。Class Nematoda: Dirofilaria immitis, Meloidogyne spp., Heterodera spp., Hoplolaimus columbus, Belonolaimus spp., root rot Nematodes (Pratylenchus spp.), kidney-shaped nematodes (Rotylenchus reniformis), decorative small ring nematodes (Criconemellaornata), stem nematodes (Ditylenchus spp.), leaf bud nematodes (Aphelenchoides besseyi), rice field hidden root nematodes (Hirschmanniella spp.).
本发明的式I所示的化合物在低浓度使用时,对于各种害虫或害螨也显示出优良的防除作用,在害虫或害螨生命周期的每一阶段(如卵、幼虫(若虫)、蛹、成虫)均具有杀虫或杀螨活性,对于那些对传统杀虫剂或杀螨剂产生了抗药性的害虫或害螨,本发明的式I化合物也显示出优良的防除活性。根据通常的生物学和/或化学的物理参数,可以用多种方式配制式I化合物。适合的制剂选择实例为:可湿性粉剂(WP)、可湿性液剂(SL)、可溶性粉剂(SP)、可分散液剂(DC)、水剂(AS)、微乳剂(ME)、乳油(EC)、水乳剂(EW)、可喷洒溶液、悬浮剂(SC)、可分散油悬浮剂(OD)、粉剂(DP)、微囊悬浮剂(CS)、水分散粒剂(WG)、水溶性粒剂(SG)、大粒剂(GG)、用于撒播和土壤施药的颗粒剂(GR)、气雾剂(AE)、超低容量剂(ULV)和蜡制品。必要的制剂助剂,例如惰性物质、表面活性剂、溶剂及其它添加剂。When used at low concentrations, the compound represented by formula I of the present invention also shows excellent control effects against various pests or pest mites. Both pupae and adults have insecticidal or acaricidal activity. The compound of formula I of the present invention also shows excellent control activity against those pests or mites that have developed resistance to traditional insecticides or acaricides. The compounds of formula I can be formulated in a variety of ways, depending on the usual biological and/or chemical physical parameters. Examples of suitable formulation options are: wettable powder (WP), wettable liquid (SL), soluble powder (SP), dispersible liquid (DC), aqueous (AS), microemulsion (ME), emulsifiable concentrate ( EC), water emulsion (EW), sprayable solution, suspension concentrate (SC), dispersible oil suspension (OD), powder (DP), microencapsulated suspension (CS), water-dispersible granule (WG), water-soluble granules (SG), large granules (GG), granules for broadcast and soil application (GR), aerosols (AE), ultra-low volumes (ULV) and wax products. Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives.
在混配制剂或桶混制剂中,可以和本发明的活性物质混合的合适的活性物质为,例如《农药手册》(北京:化学工业出版社,2015年5月第1版)中的已知物质。例如以下提到的杀虫活性物质可以和
式I化合物混合(备注:化合物的名称,或者为根据国际标准化组织(ISO)的普通名称,或者为化学名称,适当的时候有代号):抗生素类杀虫剂(例如,阿洛氨菌素(allosamidin)和苏云金素);大环内酯杀虫剂(例如,多杀菌素、spinetoram、和其它包括21-丁基刺糖菌素的刺糖菌素(spinosyns)及其衍生物);阿维菌素杀虫剂例如,阿维菌素(abamectin)、多拉菌素、埃玛菌素、埃普利诺菌素、伊维菌素和塞拉菌素;密比霉素杀虫剂例如,lepimectin、密灭汀、杀螨菌素肟和莫西菌素);含砷杀虫剂例如,砷酸钙、乙酰亚砷酸铜、砷酸铜、砷酸铅、亚砷酸钾和亚砷酸钠;生物杀虫剂例如金龟子芽孢杆菌(Bacilluspopilliae)、球形芽孢杆菌(B.sphaericus)、苏云金芽孢杆菌鲇泽亚种(B.thuringiensis subsp.aizawai)、苏云金芽孢杆菌kurstaki亚种(B.thuringiensis subsp.kurstaki)、苏云金芽孢杆菌拟步甲亚种(B.thuringiensis subsp.tenebrionis)、白僵菌(Beauveria bassiana)、日本金龟顆粒病毒(Cydia pomomella granulosis virus)、斜纹夜蛾核多角体病毒(NPV)(Douglas fir tussock moth NPV)、舞毒蛾NPV(gypsy mothNPV)、谷实夜蛾NPV(Helicoverpa zea MPV)、印度谷螟颗粒体病毒(India meal moth granulosis virus)、金龟子绿僵菌(Metarhiziumanisopliae)、蝗虫微孢子虫(Nosema locustae)、玫烟色拟青霉(Paecilomyces fumosoroseus)、淡紫拟青霉(P.lilacinus)、发光杆菌(Photorhabdus luminescens)、甜菜夜蛾NPV(Spodoptera exiguaNPV)、胰蛋白酶调节oostatic因子(trypsin modulating oostatic factor)、嗜线虫致病杆菌(Xenorhabdus nematophilus)、和伯氏致病杆菌(Xbovienii),植物加入保护杀虫剂例如Cry1Ab、Cry1Ac、Cry1F、Cry1A.105、Cry2Ab2,Cry3A、mirCry3A、Cry3Bb1、Cry34、Cry35和VIP3A;植物杀虫剂例如,新烟碱、印楝素、d-柠檬烯、烟碱、除虫菊素、瓜菊酯、瓜菊酯I、瓜菊酯II、茉酮菊素I、茉酮菊素II、除虫菊酯I、除虫菊酯II、苦木药(quassia)、鱼藤酮、ryania和藜芦碱);氨基甲酸酯类杀虫剂例如,恶虫威和甲萘威;苯并呋喃基甲基氨基甲酸酯杀虫剂例如,丙硫克百威、克百威、丁硫克百威、decarbofuran和呋线威);二甲基氨基甲酸酯杀虫剂(例如,dimitan、敌蝇威、hyquincarb和抗蚜威);肟氨基甲酸酯杀虫剂(例如,棉铃威、涕灭威、涕灭砜威、丁酮威、丁酮砜威、灭多威、戊氰威、杀线威、噻螨威、抗虫威、硫双威和久效威);苯基甲基氨基甲酸酯杀虫剂(例如,除害威、灭害威、合杀威、畜虫威、氯杀灭威、除线威、dicresyl、二养威、EMPC、乙硫苯威、fenethacarb、仲丁威、异丙威、甲硫威、速灭威、兹克威、蜱虱威、猛杀威、残杀威、混杀威、XMC和灭杀威);二硝基苯酚类杀虫剂(例如,消螨酚、丙硝酚、戊硝酚和DNOC);氟类杀虫剂(例如,六氟硅酸钡、冰晶石、氟化钠、六氟硅酸钠和氟虫胺);甲脒类杀虫剂(例如,双甲脒、杀虫脒、伐虫脒和formparanate);熏蒸剂类杀虫剂(例如,丙烯腈、二硫化碳、四氯化碳、氯仿、氯化苦、对二氯苯、1,2-二氯丙烷、甲酸乙酯、1,2-二氯乙烷、环氧乙烷、氰化氢、碘甲烷、甲基溴、甲基氯仿、二氯甲烷、奈、膦、硫酰氟和四氯乙烷);无机杀虫剂(例如,硼砂、石硫合剂、油酸铜、氯化亚汞、硫氰酸钾和硫氰酸钠);几丁质合成抑配方(例如,双三氟虫脲、噻嗪酮、定虫隆、灭蝇胺、除虫脲、氟环脲、氟虫脲、氟铃脲、虱螨脲、敌草胺(novaluron)、多氟脲(noviflumuron)、氟幼脲、氟苯脲和杀铃脲);拟保幼激素(例如,保幼醚(epofenonane)、苯氧威、烯虫乙酯、烯虫炔酯、烯虫酯、吡丙醚和烯虫硫酯);保幼激素(例如,保幼激素I、保幼激素II、保幼激素III);蜕皮激素促效药(例如,环虫酰肼、氟虫酰肼、甲氧虫酰肼和虫酰肼);蜕皮激素(例如,α-蜕皮素和蜕皮甾醇);蜕皮抑配方(例如,苯虫醚);早熟素(precocenes)(例如,早熟素I、早熟素II、早熟素III);无类别昆虫生
长调节剂(例如,环虫腈(dicyclanil));沙蚕毒素类似物(nereistoxin analogue)杀虫剂(例如,杀虫磺、杀螟丹、杀虫环和杀虫双(thiosultap));烟碱类杀虫剂(例如,氟啶虫酰胺);硝基胍类杀虫剂(例如,可尼丁、呋虫胺、吡虫啉和噻虫嗪);硝基亚甲基(nitromethylene)类杀虫剂(例如,烯啶虫胺和硝噻嗪(nithiazine));吡啶基甲基胺杀虫剂(例如,啶虫脒、烯啶虫胺和噻虫啉);有机氯杀虫剂(例如,溴-DDT、毒杀芬、DDT、pp’-DDT、乙基-DDD、HCH、γ-HCH、林丹、甲氧滴滴涕、五氯苯酚和TDE);环二烯类杀虫剂(例如,艾氏剂、溴杀烯、冰片丹、氯丹、开蓬(chlordecone)、狄氏剂、dilor、硫丹、异狄氏剂、HEOD、七氯、HHDN、碳氯灵、异艾剂、克莱范和灭蚁灵);有机磷酸酯类杀虫剂(例如,bromfenvinfos、毒虫畏、巴毒磷、敌敌畏、百治磷、甲基毒虫畏、甲基氯吡磷、庚烯磷、methocrotophos、速灭磷、久效磷、二溴磷、萘肽磷、磷胺、丙虫磷、TEPP和沙虫畏);有机硫代磷酸酯类杀虫剂(例如,蔬果磷、丁苯硫磷和稻丰散);脂肪族有机硫代磷酸酯类杀虫剂(例如,家蝇磷、胺吸磷(amiton)、硫线磷、氯氧磷、氯甲硫磷、田乐磷、田乐磷-O、田乐磷-S、内吸磷、内吸磷-O、内吸磷-S、甲基内吸磷、O-甲基-内吸磷、S-甲基-内吸磷、砜吸磷(demeton-S-methylsulphon)、乙拌磷、乙硫磷、灭线磷、IPSP、异拌磷、马拉硫磷、虫螨畏、亚砜磷、异亚砜磷、砜拌磷、甲拌磷、治螟磷、特丁硫磷和甲基乙拌磷);脂肪族酰胺有机硫代磷酸酯类杀虫剂(例如,赛硫磷、果虫磷、乐果、益硫磷、安硫磷、灭蚜磷、养乐果、发硫磷、苏硫磷和蚜灭磷);肟有机硫代磷酸酯类杀虫剂(例如,氯辛硫磷、辛硫磷和甲基辛硫磷);杂环有机硫代磷酸酯类杀虫剂(例如,甲基吡噁磷、蝇毒磷、畜虫磷、敌恶磷、因毒磷、灭蚜硫磷、茂硫磷、伏杀硫磷、吡唑硫磷、哒嗪硫磷和quinothion);苯并噻喃有机硫代磷酸酯类杀虫剂(例如,duthicrofos和thicrofos);苯并三嗪有机硫代磷酸酯类杀虫剂(例如,乙基谷硫磷和甲基谷硫磷);异吲哚有机硫代磷酸酯类杀虫剂(例如,氯亚胺硫磷和亚安硫磷);异噁唑有机硫代磷酸酯类杀虫剂(例如,恶唑磷和zolaprofos);吡唑并嘧啶有机硫代磷酸酯类杀虫剂(例如,chlorprazophos和吡菌磷);吡啶有机硫代磷酸酯类杀虫剂(例如,毒死蜱和甲基毒死蜱);嘧啶有机硫代磷酸酯类杀虫剂(例如,butathiofos、二嗪磷、乙嘧硫磷、lirimfos、乙基嘧啶磷、甲基嘧啶磷、primidophos、嘧硫磷和丁嘧硫磷(tebupirimfos));喹喔啉有机硫代磷酸酯类杀虫剂(例如,喹硫磷和甲基喹硫磷);噻二唑有机硫代磷酸酯类杀虫剂(例如,athidathion、噻唑磷、杀扑磷和乙噻唑磷);三唑有机硫代磷酸酯类杀虫剂(例如,氯唑磷和三唑磷);苯基有机硫代磷酸酯类杀虫剂(例如,偶氮磷、溴硫磷、乙基溴硫磷、三硫磷(carbophenothion)、虫螨磷、杀螟腈、畜蜱磷、异氯磷、除线磷、etaphos、伐灭磷、皮蝇磷、杀螟硫磷、丰索磷、倍硫磷、乙基倍硫磷、速杀硫磷、碘硫磷、线虫灵、对硫磷、甲基对硫磷、芬硫磷、对氯硫磷、丙溴磷、丙硫磷、硫丙磷、双硫磷、trichlormetaphos-3和三氯丙养磷);膦酸酯类杀虫剂(例如,丁酯膦和敌百虫);硫代膦酸酯类(phosphonothioate)杀虫剂(例如,四甲磷);苯基乙基硫代膦酸酯杀虫剂(例如,地虫硫膦和毒壤膦);苯基苯基硫代膦酸酯杀虫剂(例如,苯腈膦、EPN和溴苯膦);氨基磷酸酯(phosphoramidate)类杀虫剂(例如,育畜膦、苯线磷、丁硫环磷、地胺磷、硫环磷和pirimetaphos);硫代磷酰胺酯(phosphoramidothioate)杀虫剂(例如,乙酰甲胺磷、水胺硫磷、异柳磷、甲胺磷和胺丙畏);磷酸二酰胺(phosphorodiamide)杀虫剂(例如,甲氟磷、叠氮磷、丙胺氟磷和八甲磷);噁二嗪杀虫剂(例如,茚虫威);邻苯二甲酰亚胺杀虫剂(例如,氯亚胺硫磷、亚胺硫磷和胺菊酯);吡唑杀虫剂(例如,乙酰虫腈(acetoprole)、乙
虫清(ethiprole)、氟虫腈、pyrafluprole、pyriprole、吡螨胺、唑虫酰胺和vaniliprole;拟除虫菊酯类杀虫剂(例如,氟丙菊酯、烯丙菊酯、生物烯丙菊酯、barthrin、联苯菊酯、bioethanomethrin、环虫菊酯、乙氰菊酯、氟氯氰菊酯、β-氟氯氰菊酯、氯氟氰菊酯、γ-氯氟氰菊酯、λ-氯氟氰菊酯、氯氰菊酯、α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、Zeta-氯氰菊酯、苯醚氰菊酯、溴氰菊酯、四氟甲醚菊酯、苄菊酯、炔戊菊酯、五氟苯菊酯、吡氯氰菊酯、甲氰菊酯、氰戊菊酯、顺式氰戊菊酯、氟氰戊菊酯、氟胺氰戊菊酯、氟胺氰菊酯、抗虫菊、炔咪菊酯、甲氧苄氟菊酯、氯菊酯、生物氯菊酯、transpermethrin、苯醚菊酯、右旋炔丙菊酯、拟除虫菊酯丙氟菊酯(profluthrin)、pyresmethrin、苄呋菊酯、生物苄呋菊酯、cismethrin、七氟菊酯、环戊烯丙菊酯、胺菊酯、四溴菊酯和四氟苯菊酯);拟除虫菊酯醚杀虫剂(例如,醚菊酯、三氟醚菊酯、苄螨醚、protrifenbute和氟硅菊酯);嘧啶胺(pyrimidinamine)杀虫剂(例如,flufenerim和嘧螨醚);吡咯杀虫剂(例如,溴虫腈);季酮酸杀虫剂(例如,螺螨酯,螺甲螨酯);硫脲杀虫剂(例如,丁醚脲);脲杀虫剂(例如,flucofuron和sulcofuron);以及未分类的杀虫剂(例如,AKD-3088、氯氰碘柳胺、巴豆酰甲苯胺、丁氟螨酯(cyflumetofen)、E2Y45、EXD、抗螨唑、喹螨醚(fenazaquin)、fenoxacrim、唑螨酯(fenpyroximate)、FKI-1033、flubendiamide、HGW86、氟蚁腙、IKI-2002、稻瘟灵、特螨腈、metaflumizone、恶虫酮、氟蚁灵、NNI-9850、NNI-0101、吡蚜酮、哒螨灵、啶虫丙醚、Qcide、碘醚柳胺、氯虫酰胺(rynaxypyr)、SYJ-159、苯螨噻和唑蚜威及它们的任意组合);及它们的任意组合。In mixed preparations or tank mix preparations, suitable active substances that can be mixed with the active substances of the present invention are, for example, those known in "Pesticide Handbook" (Beijing: Chemical Industry Press, 1st Edition, May 2015) substance. For example, the insecticidal active substances mentioned below can be combined with Mixture of compounds of formula I (note: the name of the compound is either a common name according to the International Organization for Standardization (ISO) or a chemical name, with a code name when appropriate): antibiotic insecticides (e.g., alobactin ( allosamidin) and thuringin); macrolide insecticides (e.g., spinosyn, spinetoram, and other spinosyns including 21-butylspinetoram and their derivatives); avectin Bacteriocin pesticides such as abamectin, doramectin, emamectin, eplenomectin, ivermectin and selamectin; mibimycin pesticides such as , lepimectin, minmetin, acarin oxime, and moxidectin); arsenic-containing pesticides such as calcium arsenate, copper acetyl arsenite, copper arsenate, lead arsenate, potassium arsenite, and Sodium arsenate; biological pesticides such as Bacillus popilliae, B. sphaericus, B. thuringiensis subsp. aizawai, B. thuringiensis kurstaki subspecies (B. thuringiensis subsp.kurstaki), B.thuringiensis subsp.tenebrionis, Beauveria bassiana, Cydia pomomella granulosis virus, Spodoptera litura nuclear polyhedrosis virus ( NPV) (Douglas fir tussock moth NPV), gypsy mothNPV (gypsy mothNPV), Helicoverpa zea MPV (Helicoverpa zea MPV), Indian meal moth granulosis virus (India meal moth granulosis virus), Metarhizium anisopliae (Metarhiziumanisopliae) , Nosema locustae, Paecilomyces fumosoroseus, P.lilacinus, Photorhabdus luminescens, Spodoptera exiguaNPV, trypsin Modulating oostatic factor (trypsin modulating oostatic factor), Xenorhabdus nematophilus, and Xbovienii, adding protective pesticides to plants such as Cry1Ab, Cry1Ac, Cry1F, Cry1A.105, Cry2Ab2, Cry3A , mirCry3A, Cry3Bb1, Cry34, Cry35, and VIP3A; plant pesticides such as neonicotinoids, azadirachtin, d-limonene, nicotine, pyrethrins, cucurrin, curerin I, curerin II, jasmine ketothrin I, jastririn II, pyrethrin I, pyrethrin II, quassia, rotenone, ryania and veratrine); carbamate insecticides such as dipiocarb and carnaphen carbofuran; benzofuranyl methylcarbamate insecticides such as carbofuran, carbofuran, carbofuran, decarbofuran and furacarb); dimethylcarbamate insecticides (e.g., dimitan, dipyrocarb, hyquincarb, and pirimicarb); oxime carbamate insecticides (e.g., aldicarb, aldicarb, aldicarb, butanthiocarb, butalthiocarb, butyrocarb acecarb, pentocyancarb, dimethiocarb, thiocarb, dipiocarb, thiodicarb, and monocarb); phenylmethylcarbamate insecticides (e.g., methiocarb, methiocarb, methiocarb Dimethiocarb, chlormethiocarb, chlormethiocarb, dimethiocarb, dicresyl, fenethacarb, EMPC, ethiobencarb, fenethacarb, sembutylcarb, isopropylcarb, methiocarb, dicresyl, zikocarb, pyrozocarb, mesoxur, propoxur, mixedoxur, Pesticides (e.g., barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate, and sulfluramid); formamidine insecticides (e.g., sulfamidamidine, acetimidamid, valfenamid and formparanate); fumigant pesticides (for example, acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform, chloropicrin, p-dichlorobenzene, 1,2-dichloropropane, ethyl formate, 1,2- Dichloroethane, ethylene oxide, hydrogen cyanide, methyl iodide, methyl bromide, methyl chloroform, methylene chloride, naphtha, phosphine, sulfuryl fluoride and tetrachloroethane); inorganic pesticides (e.g., Borax, lime sulfur, copper oleate, mercurous chloride, potassium thiocyanate and sodium thiocyanate); chitin synthesis inhibitor formulations (e.g., triflufenuron, buprofen, difenzofuron, thiocyanate Cyprosamine, diflubenzuron, fluflubenzuron, fluflubenzuron, fluflubenzuron, lufenuron, novaluron, noviflumuron, fluflubenzuron, fluflubenzuron and fluflubenzuron); Juvenile hormones (e.g., epofenonane, fenoxycarb, methoprene, methoprene, methoprene, pyriproxyfen, and thiomethoxy); juvenile hormones (e.g., Hormone I, juvenile hormone II, juvenile hormone III); ecdysone agonists (e.g., cyclofenozide, flufenozide, methoxyfenozide, and tebufenozide); ecdysone (e.g., α- Ecdysone and ecdysterol); ecdysis-inhibiting formulas (e.g., befendifen); precocenes (e.g., precocene I, precocene II, precocene III); unclassified insect organisms long-term regulators (e.g., dicyclanil); nereistoxin analogue insecticides (e.g., fenfosulfonate, fenitroth, cyclofenac, and thiosultap); tobacco Alkali insecticides (e.g., sulfonicamid); nitroguanidine insecticides (e.g., canidine, dinotefuran, imidacloprid, and thiamethoxam); nitromethylene insecticides agents (e.g., nitenpyram and nithiazine); pyridylmethylamine pesticides (e.g., acetamiprid, nitenpyram, and thiacloprid); organochlorine pesticides (e.g., bromo-DDT, toxaphene, DDT, pp'-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor, pentachlorophenol, and TDE); cyclic diene pesticides (e.g., mugwort Bromicide, bromifene, bornanol, chlordane, chlordecone, dieldrin, dilor, endosulfan, endrin, HEOD, heptachlor, HHDN, carboxylin, isodromycin, clay and mirex); organophosphate insecticides (e.g., bromfenvinfos, fenfos, methophos, dichlorvos, dichlorphos, methylfenfos, methylclofenfos, heptenophos, methocrotophos, methocrotophos, phosphonate, monocrotophos, dibromophos, naphthionphos, phosphatamine, prophophophos, TEPP and sandworm); organothiophosphate insecticides (e.g., vegetaphos, fenfenthion and fenfenphos) Powder); aliphatic organophosphorothioate insecticides (e.g., housefly, amiton, phosphorus, oxychloride, methylthionate, tenophos, tenophos-O , Tianlephos-S, Systemophos, Systemophos-O, Systemophos-S, Methyl systemophos, O-methyl-systemophos, S-methyl-systemophos, Sulfonophos (demeton-S-methylsulphon), acetophos, ethionphos, methiophos, IPSP, isofon, malathion, pyrophosphonate, sulfoxide, isosulfoxide, sulfonphos, phorate phosphorus, phosphorus, terbuphos and methylphosphonate); aliphatic amide organophosphorothioate insecticides (e.g., thionphos, dimethoate, dimethoate, ethion, ethion phoxim, phoxim, dimethoate, phoxim, thionophos, and phoxim); oxime organothiophosphate insecticides (e.g., phoxim, phoxim, and methylphoxim ); Heterocyclic organophosphorothioate pesticides (for example, pyrophos-methyl, pyrophos, phosphos, dimethophos, phosphos, pyrothion, thiophos, phosphos phosphorus, pyrazothion, pyridazinophos, and quinothion); benzothiopyran organothiophosphate insecticides (e.g., duthicrofos and thicrofos); benzotriazine organothiophosphate insecticides (e.g., duthicrofos and thicrofos) For example, azinphos-ethyl and azinphos-methyl); isoindole organophosphorothioate insecticides (for example, chlorethion and phosphin); isoxazole organothiophosphates pesticides (e.g., oxazophos and zolaprofos); pyrazolopyrimidine organothiophosphate pesticides (e.g., chlorprazophos and pyridinate); pyridine organothiophosphate pesticides (e.g., chlorpyrifos and chlorpyrifos-methyl); pyrimidine organophosphorothioate insecticides (e.g., butathiofos, diazinon, pyrimethionate, lirimfos, ethylpyrimidinphos, methylpyrimidinphos, primidophos, pyrimidinphos, and butathiofos tebupirimfos); quinoxaline organothiophosphate insecticides (e.g., quinalphos and methylquinalphos); thiadiazole organothiophosphate insecticides (e.g., athidathion , thiazophos, ethazophos and ethiazophos); triazole organothiophosphate insecticides (e.g., chlorazofos and triazophos); phenyl organothiophosphate insecticides (e.g., Azophos, bromophos, ethyl bromophos, carbophenothion, fenfothion, fenitrothion, phosphos, isochlorphos, ethylphos, etaphos, valfenphos, dermaphos , fenithion, fenthion, fenthion, ethyl fenthion, fenthion, iodophos, nematophos, parathion, methyl parathion, fenthion, parachlorthion , profenofos, prothion, thiophos, dithion, trichlormetaphos-3, and trichlormetaphos); phosphonate insecticides (e.g., butylphosphonate and trichlorfon); thiophosphonates Phosphonothioate pesticides (e.g., tetramethylphosphonate); phenylethylphosphonothioate pesticides (e.g., methotrexate and pyrophosphine); phenylphenylphosphonothioate Ester pesticides (for example, phenylphosphine, EPN and bromophenylphosphonate); phosphoramidate pesticides (for example, phosphine, difenfosine, butaphos, difendophos, thiocycline phosphorus and pirimetaphos); phosphoramidothioate insecticides (e.g., acephate, acetophos, isosaphos, methamidophos, and profenam); phosphorodiamide insecticides pesticides (e.g., methylfluorophos, azidophos, propylamine, and octamethonate); oxadiazine pesticides (e.g., indoxacarb); phthalimide pesticides (e.g., chloracetate) acetoprole, acetoprole, and metamethrin); pyrazole insecticides (e.g., acetoprole, acetoprole); Ethiprole, fipronil, pyrafluprole, pyriprole, fenpyrpyronil, pyrafluprole, and vaniliprole; pyrethroid insecticides (e.g., flumethrin, allethrin, bioallethrin, barthrin, bifenthrin, bioethanomethrin, cypermethrin, cyhalothrin, cyfluthrin, beta-cyhalothrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin , α-cypermethrin, β-cypermethrin, θ-cypermethrin, Zeta-cypermethrin, cypermethrin, deltamethrin, perfluthrin, permethrin, pentythrin, penfluthrin, Cypermethrin, fenpropathrin, fenvalerate, cis-fenvalerate, fluvalerate, fluvalinate, fluvalinate, pyrethrin, fenvalerate, methoxy Perfluthrin, permethrin, biopermethrin, transpermethrin, phenethrin, dexpropargyl, pyrethroid profluthrin, pyresmethrin, permethrin, biopermethrin esters, cismethrin, tefluthrin, cyclomethrin, fenmethrin, deltamethrin, and transfluthrin); pyrethroid ether insecticides (e.g., fenmethrin, trifluthrin esters, befenerim, protrifenbute, and flumethrin); pyrimidinamine insecticides (e.g., flufenerim and pyrimidine); azole insecticides (e.g., bromiprene); tetrafenac insecticides (e.g., spirodiclofen, spirodifenfen); thiourea insecticides (e.g., difenthiuron); urea insecticides (e.g., flucofuron and sulcofuron); and unclassified insecticides (e.g., AKD- 3088, clofenacrim, crotonyltoluidide, cyflumetofen, E2Y45, EXD, fenazaquin, fenoxacrim, fenpyroximate, FKI-1033, flubendiamide , HGW86, flumefenhydrazone, IKI-2002, pyridoxin, metaflumizone, metaflumizone, metaflumizone, flumefenfen, NNI-9850, NNI-0101, pymetrozine, pyridafen, acetamiprid, Qcide, iodosamide, chlorantraniliprole (rynaxypyr), SYJ-159, fenfenzofen, and fenpyrpyr, and any combination thereof); and any combination thereof.
部分可以与本发明化合物结合使用的杀菌剂包括:2-(氰硫基甲硫基)-苯并噻唑、2-苯基苯酚、8-羟基喹啉硫酸盐、白粉寄生孢、使君子(quisqualis)、氧环唑、嘧菌酯、枯草芽孢杆菌、苯霜灵、苯菌灵、苯噻菌胺、苄氨基苯-磺酸盐(BABS)盐、碳酸氢盐、联苯、叶枯唑、联苯三唑醇、灰瘟素、硼砂、波尔多混合剂、啶酰菌胺、糠菌唑、乙嘧酚磺酸酯、石硫合剂、敌菌丹、克菌丹、多菌灵、萎绣灵、环丙酰菌胺、香芹酮、地茂散(Chloroneb)、百菌清、乙菌利、盾壳霉、氢氧化铜、辛酸铜、王铜、硫酸铜、碱式硫酸铜(copper sulfate(tribasic))、氧化亚铜、氰霜唑、syflufenamid、霜脲氰、环丙唑醇、嘧菌环胺、棉隆、咪菌威、乙撑双-(二硫代氨基甲酸)联铵(diammoniumethylenebis-(dithio carbamate))、苯氟磺胺、双氯酚、双氯氰菌胺、哒菌清、二氯喃、乙霉威、苯醚甲环唑、燕麦枯离子(difenzoquat ion)、氟嘧菌胺、烯酰吗啉、醚菌胺、烯唑醇、烯唑醇-M、消螨通、敌螨普、二苯胺、二氰蒽醌、吗菌灵、吗菌灵醋酸盐、多果定、多果定游离碱、敌瘟磷、氟环唑、噻唑菌胺、乙氧喹啉、土菌灵、恶唑菌酮、咪唑菌酮、氯苯嘧啶醇、腈苯唑、甲呋酰胺(fenfuram)、环酰菌胺、氰菌胺、拌种咯、苯锈啶、丁苯吗啉、三苯锡、三苯基乙酸锡、三苯基氢氧化锡、福美铁、嘧菌腙、氟啶胺、咯菌腈、氟吗啉、氟啶酰菌胺、氟氯菌核利、氟嘧菌酯(fluoxastxobin)、氟喹唑、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、甲醛、三乙膦酸、三乙膦酸铝、麦穗宁、呋霜灵、呋吡菌胺、双胍辛、双胍辛乙酸盐、GY-81、六氯苯、己唑醇、恶霉灵、抑霉唑、高效抑霉唑、亚胺唑、双胍辛胺、双胍辛胺乙酸盐、双胍三辛烷基苯磺酸盐(iminoctadine tris(albesilate))、种菌唑、异稻瘟净、异菌脲、异丙菌胺、稻瘟灵、春雷霉素、春雷霉素水合盐酸盐(kasugamycin hydrochloride hydrate)、醚菌酯、代森锰铜、代森锰锌、代森锰、嘧菌胺、灭锈胺、氯化汞、氧化汞、氧化亚汞、甲霜灵、精甲霜灵、高效甲霜灵、威百亩、安百亩、威百亩-钾(metam-pitassium))、威百亩-钠(metam-sodium)、叶菌唑、磺菌威、甲基碘、异硫氰酸甲酯、代森联、
苯氧菌胺、苯菌酮、灭粉霉素、腈菌唑、代森钠、肽菌酯、氟苯嘧啶醇、辛噻酮、呋酰胺、油酸(脂肪酸)、肟醚菌胺、恶霜灵、喹啉铜、恶咪唑富马酸盐、氧化萎锈灵、稻瘟酯、戊菌唑、戊菌隆、五氯苯酚、月桂酸五氯苯酯、吡噻菌胺、乙酸苯汞、膦酸、稻瘟酞、啶氧菌酯、多抗霉素-B、多抗霉素、多氧霉素、碳酸氢钾、羟基喹啉硫酸钾、烯丙苯噻唑、咪鲜胺(prochloraz,)、腐霉利、霜霉威、霜霉威盐酸盐、丙环唑、丙森锌、丙氧喹啉、丙硫菌唑、唑菌胺酯、吡菌磷、稗草丹、啶斑肟、嘧霉胺、咯喹酮、灭藻醌、苯氧喹啉、五氯硝基苯、大虎杖(Reynoutria sachalinensis)提取物、硅噻菌胺、硅氟唑、2-苯基苯酚钠、碳酸氢钠、五氯苯酚钠、螺环菌胺、硫磺、SYP-Z071、焦油油剂、戊唑醇、四氯硝基苯、四氟醚唑、噻菌灵、噻呋酰胺、甲基硫菌灵、福美双、噻酰菌胺、甲基立枯磷、甲苯氟磺胺、三唑酮、三唑醇、咪唑嗪、三环唑、十三吗啉、肟菌酯、氟菌唑、嗪胺灵、灭菌唑、有效霉素、乙烯菌核利、代森锌、福美锌、苯酰菌胺、橄榄假丝酵母、尖孢镰刀菌、粘帚霉属、Phlebiopsis gigantean、灰绿链霉菌、木霉属、(RS)-N-(3,5-二氯苯基)-2-(甲氧基甲基)-琥珀酰亚胺、1,2-二氯丙烷、1,3-二氯-1,1,3,3-四氟丙酮水合物、1-氯-2,4-二硝基萘、1-氯-2-硝基苯烷、2-(2-十七烷基-2-咪唑啉-1-基)乙醇、2,3-二氢-5-苯基-1,4-dithi-inel,1,4,4-四氧化物、2-甲氧基乙基汞乙酸酯、2-甲氧基乙基汞氯化物、2-甲氧基乙基汞硅酸酯、3-(4-氯苯基)-5-甲基绕丹宁、4-(2-硝基丙-1-烯基)苯基thiocyanateme:氨丙膦酸、敌菌灵、氧化福美双杀菌剂、多硫化钡、Bayer 32394、麦锈灵、醌肟腙、环草敌、benzamacril;benzamacril-isobutyl、benzamorf、乐杀螨、双(甲基汞)硫酸盐、氧化双(三丁基锡)、丁硫啶、镉钙铜锌铬酸盐硫酸盐(cadmium calcium copperzinc chromate sulfate)、吗菌威、CECA、chlobenthiazone、chloraniformethan、2-(2-氯苯基)-1H-苯并咪唑(chlorfenazole)、四氯喹恶啉、咪菌酮、二(3-苯基水杨酸)铜、铬酸铜锌、硫杂灵、硫酸亚铜肼、cuprobam、环菌胺、氰菌灵、酯菌胺、癸磷锡、二氯奈醌、菌核利、苄氯三唑醇、二甲嘧酚、敌菌死、硝辛酯杀螨剂、硝丁酯、双吡硫翁、灭菌磷、多地辛、肼菌酮、EBP、ESBP、乙环唑、代森硫、ethirim、敌磺钠、咪菌腈、种衣酯、三氟苯唑、二甲呋酰胺、呋菌胺、呋醚唑、茂谷乐(furmecyclox)、呋甲硫菌灵、glyodine、灰荑霉素、丙烯酸喹啉酯、Hercules 3944、hexylthiofos、ICIA0858、isopamphos、isovaledione、邻酰胺、mecarbinzid、metazoxolon、呋菌胺、甲基汞双氰胺、噻菌胺、代森环、粘氯酸酐、甲菌利、N-3,5-二氯苯基-琥珀酰亚胺、N-3-硝基苯基衣康酰亚胺、纳他霉素、N-乙基mercurio-4-甲苯磺酰苯胺、双(二甲基二硫代氨基甲酸)镍、OCH、二甲基二硫代氨基甲酸苯基汞、硝酸苯基汞、氯瘟磷、硫菌威;硫菌威盐酸盐、比锈灵、啶菌腈、氯甲氧吡啶、氯吡根呋醚、quinacetol;quinacetol sulfate、醌菌腙、quinconazole、rabenzazole、水杨酰苯胺、SSF-109、戊苯砜、tecoram、thiadifluor、噻菌腈、thiochlorfenphim、硫菌灵、克杀螨、tioxymid、威菌磷、嘧菌醇、丁三唑、水杨菌胺、福美甲胂、XRD-563和氰菌酯,以及它们的任何混合。Some of the fungicides that can be used in combination with the compounds of the present invention include: 2-(cyanothiomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, leucospora, quisqualis ), oxyconazole, azoxystrobin, Bacillus subtilis, benoxyl, benomyl, benthiazole, benzylinobenzene-sulfonate (BABS) salt, bicarbonate, biphenyl, phytonzolin, Diphenyltriazole, gray blastin, borax, Bordeaux mixture, boscalid, furfuroconazole, pyrimethonol sulfonate, lime sulfur mixture, captafant, captan, carbendazim, phosphine Spirit, cycloprofen, carvone, Dimaosan (Chloroneb), chlorothalonil, ethanol, Copper hydroxide, copper octoate, copper king, copper sulfate, basic copper sulfate (copper sulfate (tribasic)), cuprous oxide, cyanazole, syflufenamid, cymoxanil, cyproconazole, cyprodinium, methicillin, imidacarb, ethylene bis-(dithiocarbamate) (diammoniumethylenebis-(dithio carbamate)), benzofonamide, diclofenac, diclofenac, diclofenac, diclofenac, dimethocarb, difenoconazole, difenzoquat ion, fluoride Dimethoprim, dimethomorph, dimethoxystrobin, difenconazole, difenconazole-M, Dimethonazole, Dimethop, Diphenylamine, Dicyanoanthraquinone, Mobendazim, Mobendazole acetate, Dipyridin, Dipyridin free base, difenfosin, epoxiconazole, thiazolin, ethoxyquin, terabendazole, oxathiazolin, imidazolin, chlorfenacil, nitrile azole, ethoxyquin Furamide (fenfuram), fenfuram, cyprofen, seed dressing, fenpropidine, fenpropion, triphenyltin, triphenyltin acetate, triphenyltin hydroxide, ferrocarbamate, azoxysporin Hydrazone, fluazinam, fludioxonil, flumorphaline, fluboclofen, fluoxastrobin, fluoxastrobin (fluoxastxobin), fluquinazole, flusilazole, sulfonamid, fluoxonamide, powder Triethyl phosphonate, triethyl phosphonate, aluminum triethyl phosphonate, mesinin, furalaxyl, folopiper, biguanide, biguanide acetate, GY-81, hexachlorobenzene, Hexaconazole, imazalil, imazalil, imazalil, iminazole, biguanitamine, biguanitamine acetate, iminoctadine tris(albesilate), species Isoprodione, isopyrimidin, iprodione, isoprofen, kasugamycin, kasugamycin hydrochloride hydrate, kasugamycin, mancobale, maneb Zinc, maneb, azoxystrobin, promethazine, mercuric chloride, mercury oxide, mercury oxide, metalaxyl, metalaxyl fine, high-efficiency metalaxyl, metamu, metamu, and metabimu -Potassium (metam-pitassium), metam-sodium, metaconazole, sulfonatecarb, methyl iodide, methyl isothiocyanate, methionine, Mefenoxystrobin, fenoxystrobin, fenclomycin, myclobutanil, sodium chloride, peptidostrobin, flufenopyrimidine, octathialone, furamide, oleic acid (fatty acid), oximestrobin, oxamid Frost spirit, quinoline copper, oxamidazole fumarate, oxycarboxylate, rice blast ester, penconazole, pencloconazole, pentachlorophenol, pentachlorophenyl laurate, pyrithiopyramide, phenylmercuric acetate , phosphonic acid, blast phthalide, picoxystrobin, polymycin-B, polymycin, polyoxymycin, potassium bicarbonate, potassium hydroxyquinoline sulfate, allylbenthiazole, prochloraz ,), procymidazole, propamocarb, propamocarb hydrochloride, propiconazole, prosodium zinc, propoxyquin, prothioconazole, pyraclostrobin, pyriclophos, barnyard grass, pyraclostrobin Panoxime, pyrimethanil, pyroquinone, quinone, phenoxyquinone, pentachloronitrobenzene, giant knotweed (Reynoutria sachalinensis) extract, silothiaphen, siloflurazole, sodium 2-phenylphenolate , sodium bicarbonate, sodium pentachlorophenol, spironazine, sulfur, SYP-Z071, tar oil, tebuconazole, tetrachloronitrobenzene, tetrafluoropropazole, thiabendazole, thiofuramide, methyl Thiophanate, thiram, thiostrobin, methylcumfos, tolufenamide, triadimefon, triadimefon, imidazolin, tricyclazole, tritrimorpholine, trifloxystrobin, trifluconazole, Tricarbazole, fenclozolin, valmycin, vinclozolin, tetrazine, thiramizin, benzamide, Candida oleifera, Fusarium oxysporum, Myxosporum spp., Phlebiopsis gigantean, grey-green chain Mold, Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3- Dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitrononaphthalene, 1-chloro-2-nitrophenyl, 2-(2-heptadecanyl -2-Imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-inel, 1,4,4-tetraoxide, 2-methoxyethylmercury Acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2- Nitroprop-1-enyl)phenylthiocyanateme: amphosphonate, diprofen, thiram oxide, barium polysulfide, Bayer 32394, phosphine, quinone oxime hydrazone, cyclofenac, benzamacril; benzamacril -isobutyl, benzamorf, bis(methylmercury) sulfate, bis(tributyltin) oxide, thiobutyl, cadmium calcium copperzinc chromate sulfate (cadmium calcium copperzinc chromate sulfate), mobicarb, CECA, chlobenthiazone, chloraniformethan, 2-(2-chlorophenyl)-1H-benzimidazole (chlorfenazole), tetrachloroquinoxaline, imidazone, copper bis(3-phenylsalicylate), copper zinc chromate , thiamethaline, cuprous hydrazine sulfate, cuprobam, cyclostrobin, cyprostrobin, cyclostrobin, tin decylphosphonate, diclofenac, sclerotium, benzylchlorotriazole, dimethacinol, and antibiotics Diesel, nitroxate acaricide, nitrobutyl, dipyrithione, pyrithione, dodesin, hydromeprodone, EBP, ESBP, econazole, sulfonate, ethirim, sodium pyrithione, imidazole Nitriles, seed coat esters, triflubendazole, dimethofuramide, furosemide, furfurazole, furmecyclox, thiophanate, glycodine, griseocycline, quinoline acrylate, Hercules 3944 , hexylthiofos, ICIA0858, isopamphos, isovaledione, o-amide, mecarbinzid, metazoxolon, furosemide, methylmercuric dicyandiamide, thiobenzidine, desencycline, mycoanhydride, mecarbinzid, N-3,5-di Chlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, bis(dimethyldithioamino) Nickel formate, OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, chlorfenphosate, thiobutanarb; thiobutanarb hydrochloride, bistrogen, picopyronil, pyridine chloride , quinacetol; quinacetol sulfate, quinone hydrazone, quinconazole, rabenzazole, salicylanilide, SSF-109, pentyl sulfone, tecoram, thiadifluor, thiochlorfenphim, thiophanate, gram miticide .
由于采用了上述技术方案,本发明的有益效果是:Due to the adoption of the above technical solutions, the beneficial effects of the present invention are:
通过对具有联苯硫醚结构的芳基硫化物进行化学修饰和分子设计,在苯环的特定位置设置取代基,得到了一系列更加高效、可用于农业或林业杀虫或杀螨用的具有极佳活性的化合物,尤其针对朱砂叶螨、二斑叶螨、神泽氏叶螨﹑柑桔全爪螨等为代表的叶螨类显示出卓越的防治效果,尤为突出的是其具有较佳的作物安全性和靶标特异性。
By chemically modifying and molecularly designing aryl sulfides with a biphenyl sulfide structure, and placing substituents at specific positions of the benzene ring, a series of more efficient compounds with insecticidal or acaricidal properties that can be used in agriculture or forestry were obtained. Excellent active compounds, especially against spider mites represented by cinnabar spider mites, two-spotted spider mites, Kanzawa spider mites, citrus panonychus, etc., showing excellent control effects. What is particularly outstanding is that it has better crop safety and target specificity.
下面将结合本发明实施例,对本发明实施例中的技术方案进行清楚、完整地描述。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts fall within the scope of protection of the present invention.
通过对所合成的化合物的经济性、多样性以及生物活性进行综合考量,优选了部分化合物列于下表中。具体的化合物结构如表1所示、具体的化合物物性数据如表2所示。表1-2中的化合物只是为了更好的说明本发明,并不会对本发明产生限定,本领域的技术人员不应将此理解为本发明上述主题的范围仅限于以下化合物。
Through comprehensive consideration of the economy, diversity, and biological activity of the synthesized compounds, some of the preferred compounds are listed in the table below. The specific compound structure is shown in Table 1, and the specific compound physical property data is shown in Table 2. The compounds in Table 1-2 are only for better illustrating the present invention and do not limit the present invention. Those skilled in the art should not understand this to mean that the scope of the above subject of the present invention is limited to the following compounds.
Through comprehensive consideration of the economy, diversity, and biological activity of the synthesized compounds, some of the preferred compounds are listed in the table below. The specific compound structure is shown in Table 1, and the specific compound physical property data is shown in Table 2. The compounds in Table 1-2 are only for better illustrating the present invention and do not limit the present invention. Those skilled in the art should not understand this to mean that the scope of the above subject of the present invention is limited to the following compounds.
表1式I化合物结构
Table 1 Structure of compounds of formula I
Table 1 Structure of compounds of formula I
表2 1H NMR数据
Table 2 1H NMR data
Table 2 1H NMR data
制备本发明化合物的方法在以下技术方案和实施例中进行了说明。原料可以经市场购买到或者可以通过文献中已知的方法或者如详解所示进行制备。本领域技术人员应当理解,也可以利用其它合成路线合成本发明的化合物。尽管在下文中已经对合成路线中的具体原料和条件进行了说明,但是,可以很容易地将其替换为其它类似的原料及条件,这些对本发明制备方法的变型或者变体而产生的诸如化合物的各种异构体等都包括在本发明范围内。另外,如下所述制备方法可以按照本发明公开内容、使用本领域技术人员熟知的常规化学方法进行进一步修饰。例如,在反应过程中对适当的基团进行保护等等。Methods for preparing the compounds of the present invention are illustrated in the following technical schemes and examples. The starting materials are commercially available or can be prepared by methods known from the literature or as described in detail. Those skilled in the art will understand that other synthetic routes may also be used to synthesize the compounds of the present invention. Although the specific raw materials and conditions in the synthetic route have been described below, they can be easily replaced with other similar raw materials and conditions. These modifications or variations of the preparation method of the present invention produce compounds such as Various isomers and the like are included within the scope of the present invention. In addition, the preparation methods described below can be further modified in accordance with the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protection of appropriate groups during the reaction, etc.
实施例1Example 1
N-(2-氟-4-甲基苯基)-乙酰胺的合成:
Synthesis of N-(2-fluoro-4-methylphenyl)-acetamide:
Synthesis of N-(2-fluoro-4-methylphenyl)-acetamide:
在瓶中称取2-氟-4-甲基苯胺(10.0g,80mmol,1.0eq.)、碳酸氢钠(13.4g,160mmol,2.0eq.),加入二氯甲烷(200mL)溶解,在冰水浴中缓慢滴加乙酸酐(12.2g,120mmol,1.5eq.),滴毕、移去冰水浴,室温下反应三小时,TLC(PE:EA=5:1)确认反应完毕后,将体系抽滤,因产品易凝固、因此需用二氯甲烷多次淋洗滤饼,淋洗完毕后,浓缩脱溶,得到红褐色针状晶体(11.4g,68mmol,85%)。LC-MS(ESI)[M+H]+=168.1,[M+Na]+=190.1。Weigh 2-fluoro-4-methylaniline (10.0g, 80mmol, 1.0eq.) and sodium bicarbonate (13.4g, 160mmol, 2.0eq.) in the bottle, add dichloromethane (200mL) to dissolve, and dissolve on ice. Slowly add acetic anhydride (12.2g, 120mmol, 1.5eq.) in the water bath. After the dripping is completed, remove the ice water bath and react at room temperature for three hours. After TLC (PE:EA=5:1) confirms that the reaction is complete, pump the system Filter, because the product is easy to solidify, so the filter cake needs to be rinsed with methylene chloride multiple times. After the rinse is completed, concentrate and remove the solution to obtain reddish-brown needle-shaped crystals (11.4g, 68mmol, 85%). LC-MS (ESI) [M+H] + =168.1, [M+Na] + =190.1.
实施例2Example 2
5-乙酰氨基-4-氟-2-甲基苯磺酰氯的制备:
Preparation of 5-acetamido-4-fluoro-2-methylbenzenesulfonyl chloride:
Preparation of 5-acetamido-4-fluoro-2-methylbenzenesulfonyl chloride:
在瓶中称取N-(2-氟-4-甲基苯基)-乙酰胺(10.0g,60mmol,1.0eq.),缓慢滴加25mL氯磺酸,加热60℃下加热反应,2小时后TLC监测(DCM:MeOH=10:1)反应完毕后,将反应液倒入冰水中,抽滤,滤饼用水淋洗,滤饼晾干后得到黄色固体(9.3g,35mmol,70%)。LC-MS(ESI)[M+H]+=266.1,[M+Na]+=288.1。Weigh N-(2-fluoro-4-methylphenyl)-acetamide (10.0g, 60mmol, 1.0eq.) in the bottle, slowly add 25mL of chlorosulfonic acid dropwise, and heat the reaction at 60°C for 2 hours. Post-TLC monitoring (DCM:MeOH=10:1) After the reaction is completed, pour the reaction solution into ice water, filter with suction, rinse the filter cake with water, and dry the filter cake to obtain a yellow solid (9.3g, 35mmol, 70%) . LC-MS (ESI) [M+H] + =266.1, [M+Na] + =288.1.
实施例3Example 3
N-(2-氟-5-巯基-4-甲基苯基)乙酰胺的制备:
Preparation of N-(2-fluoro-5-mercapto-4-methylphenyl)acetamide:
Preparation of N-(2-fluoro-5-mercapto-4-methylphenyl)acetamide:
在瓶中称取5-乙酰氨基-4-氟-2-甲基苯磺酰氯(9.3g,35mmol,1.0eq.)加入锌粉(22.7g,350mmol,10eq.)加入冰醋酸(100mL),加热至120℃回流反应,反应约2h后,TLC监测(EA:PE=1:1)原料消失后,降至室温后,加入冰水(100mL)和乙酸乙酯(100mL),抽滤除去过量锌粉,滤饼用乙酸乙酯淋洗。合并有机相后用饱和食盐水洗涤、无水硫酸钠干燥,抽滤,浓缩脱溶剂,得到淡黄色固体(5.4g,27mmol,77%)。LC-MS(ESI)[M+H]+=200.1,[M+Na]+=222.1。Weigh 5-acetamido-4-fluoro-2-methylbenzenesulfonyl chloride (9.3g, 35mmol, 1.0eq.) in the bottle, add zinc powder (22.7g, 350mmol, 10eq.), add glacial acetic acid (100mL), Heat to 120°C for reflux reaction. After about 2 hours of reaction, TLC monitors (EA:PE=1:1) that the raw materials disappear. After cooling to room temperature, add ice water (100 mL) and ethyl acetate (100 mL), and remove excess by suction filtration. Zinc powder, the filter cake was washed with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and concentrated to remove the solvent to obtain a light yellow solid (5.4 g, 27 mmol, 77%). LC-MS (ESI) [M+H] + =200.1, [M+Na] + =222.1.
实施例4Example 4
N-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)乙酰胺的制备:
Preparation of N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)acetamide:
Preparation of N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)acetamide:
在瓶中称取N-(2-氟-5-巯基-4-甲基苯基)乙酰胺(5.4g,27mmol,1.0eq.),加入乙腈(100mL),
碳酸钾(5.6g,40.5mmol,1.5eq.),在氮气氛围保护下,滴加入2,2,2-三氟乙基三氟甲烷磺酸酯(9.4g,40.5mmol,1.5eq.),室温搅拌过夜。TLC监测反应(PE:EA=2:1),原料消失后,加水淬灭,用二氯甲烷稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶得到粗品。硅胶柱层析(PE:EA=4:1)得到白色固体(7g,25mmol,92%)。LC-MS(ESI)[M+H]+=282.1,[M+Na]+=304.1。Weigh N-(2-fluoro-5-mercapto-4-methylphenyl)acetamide (5.4g, 27mmol, 1.0eq.) in the bottle, add acetonitrile (100mL), Potassium carbonate (5.6g, 40.5mmol, 1.5eq.), under the protection of nitrogen atmosphere, add dropwise 2,2,2-trifluoroethyl trifluoromethanesulfonate (9.4g, 40.5mmol, 1.5eq.), Stir at room temperature overnight. TLC monitors the reaction (PE:EA=2:1). After the raw materials disappear, add water to quench, dilute with dichloromethane, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, suction filter, concentrate and remove the solution to obtain the crude product . Silica gel column chromatography (PE:EA=4:1) obtained white solid (7g, 25mmol, 92%). LC-MS (ESI) [M+H] + =282.1, [M+Na] + =304.1.
实施例5Example 5
2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯胺的制备:
Preparation of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline:
Preparation of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline:
在瓶中称取N-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯基)乙酰胺(7g,25mmol,1.0eq.)加入乙醇(50mL)和水(10mL)溶解,加入浓盐酸(50mL),加热至85℃,反应约4小时后,TLC监测反应(PE:EA=5:1),原料消失后用1N NaOH溶液调节pH至中性。减压旋掉大部分甲醇,用二氯甲烷稀释后,用饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到粉红色液体(5.3g,22mmol,88%)。LC-MS(ESI)[M+H]+=240.1,[M+Na]+=262.1。Weigh N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)acetamide (7g, 25mmol, 1.0eq.) in the bottle and add Dissolve ethanol (50mL) and water (10mL), add concentrated hydrochloric acid (50mL), and heat to 85°C. After reacting for about 4 hours, monitor the reaction with TLC (PE:EA=5:1). After the raw materials disappear, adjust with 1N NaOH solution. pH to neutral. Spin off most of the methanol under reduced pressure, dilute with methylene chloride, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, concentrate and remove, to obtain a pink liquid (5.3g, 22mmol, 88% ). LC-MS (ESI) [M+H] + =240.1, [M+Na] + =262.1.
实施例6Example 6
(4-氟-5-碘-2-甲基苯基)(2,2,2-三氟乙基)硫醚的制备:
Preparation of (4-fluoro-5-iodo-2-methylphenyl)(2,2,2-trifluoroethyl) sulfide:
Preparation of (4-fluoro-5-iodo-2-methylphenyl)(2,2,2-trifluoroethyl) sulfide:
取2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基)苯胺(2.39g,10mmol,1.0eq.),用70%硫酸溶液(20mL)搅拌溶解后降温至0℃,缓慢滴加亚硝酸钠(1.02g,15mmol,1.5eq.)的水溶液,滴加完毕后在0℃下搅拌30分钟,得到重氮盐中间体。随后加入碘化钾固体(3.32g,20mmol,2.0eq.),在0℃下搅拌30分钟后,再在室温下搅拌2小时。反应结束后,加入亚硫酸氢钠溶液淬灭反应,乙酸乙酯稀释后,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到红色液体(2.45g,7mmol,70%)。LC-MS(ESI)[M+H]+=351.0。Take 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline (2.39g, 10mmol, 1.0eq.), stir and dissolve with 70% sulfuric acid solution (20mL) Then the temperature was lowered to 0°C, and an aqueous solution of sodium nitrite (1.02g, 15mmol, 1.5eq.) was slowly added dropwise. After the addition was completed, stir at 0°C for 30 minutes to obtain the diazonium salt intermediate. Potassium iodide solid (3.32g, 20mmol, 2.0eq.) was then added, and the mixture was stirred at 0°C for 30 minutes and then at room temperature for 2 hours. After the reaction, sodium bisulfite solution was added to quench the reaction. After dilution with ethyl acetate, the mixture was washed with saturated brine, the organic phases were combined, dried over anhydrous sodium sulfate, suction filtered, concentrated and desolvated to obtain a red liquid (2.45g, 7mmol ,70%). LC-MS (ESI) [M+H] + =351.0.
实施例7Example 7
(4',6-二氟-4-甲基-[1,1'-联苯]-3-基)(2,2,2-三氟乙基)硫醚的制备:
Preparation of (4',6-difluoro-4-methyl-[1,1'-biphenyl]-3-yl)(2,2,2-trifluoroethyl) sulfide:
Preparation of (4',6-difluoro-4-methyl-[1,1'-biphenyl]-3-yl)(2,2,2-trifluoroethyl) sulfide:
取(4-氟-5-碘-2-甲基苯基)(2,2,2-三氟乙基)硫醚(700mg,2mmol,1.0eq.),加入三苯基膦(50mg,0.2mmol,0.1eq.)和4-氟苯硼酸(420mg,3mmol,1.5eq.),碳酸钾(828mg,6mmol,3.0eq.),醋酸钯(44mg,0.2mmol,0.1eq.)用二氧六环(8mL)溶解,用氮气置换后,于80℃下反应4小时。反应结
束后,用乙酸乙酯稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(540mg,1.7mmol,85%)。LC-MS(ESI)[M+H]+=319.0。Take (4-fluoro-5-iodo-2-methylphenyl) (2,2,2-trifluoroethyl) sulfide (700mg, 2mmol, 1.0eq.) and add triphenylphosphine (50mg, 0.2 mmol, 0.1eq.) and 4-fluorophenylboronic acid (420mg, 3mmol, 1.5eq.), potassium carbonate (828mg, 6mmol, 3.0eq.), palladium acetate (44mg, 0.2mmol, 0.1eq.) were treated with dioxane The ring (8 mL) was dissolved, replaced with nitrogen, and reacted at 80° C. for 4 hours. reaction junction After completion, dilute with ethyl acetate, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, concentrate and remove, to obtain a white solid (540 mg, 1.7 mmol, 85%). LC-MS (ESI) [M+H] + =319.0.
实施例8Example 8
(4'-氯-6-氟-4-甲基-[1,1'-联苯]-3-基)(2,2,2-三氟乙基)硫醚的制备:
Preparation of (4'-chloro-6-fluoro-4-methyl-[1,1'-biphenyl]-3-yl) (2,2,2-trifluoroethyl) sulfide:
Preparation of (4'-chloro-6-fluoro-4-methyl-[1,1'-biphenyl]-3-yl) (2,2,2-trifluoroethyl) sulfide:
取(4-氟-5-碘-2-甲基苯基)(2,2,2-三氟乙基)硫醚(700mg,2mmol,1.0eq.),加入三苯基膦(50mg,0.2mmol,0.1eq.)和4-氟苯硼酸(468mg,3mmol,1.5eq.),碳酸钾(828mg,6mmol,3.0eq.),醋酸钯(44mg,0.2mmol,0.1eq.)用二氧六环(8mL)溶解,用氮气置换后,于80℃下反应4小时。反应结束后,用乙酸乙酯稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(587mg,1.76mmol,88%)。LC-MS(ESI)[M+H]+=335.0。Take (4-fluoro-5-iodo-2-methylphenyl) (2,2,2-trifluoroethyl) sulfide (700mg, 2mmol, 1.0eq.) and add triphenylphosphine (50mg, 0.2 mmol, 0.1eq.) and 4-fluorophenylboronic acid (468mg, 3mmol, 1.5eq.), potassium carbonate (828mg, 6mmol, 3.0eq.), palladium acetate (44mg, 0.2mmol, 0.1eq.) were treated with dioxane The ring (8 mL) was dissolved, replaced with nitrogen, and reacted at 80° C. for 4 hours. After the reaction was completed, it was diluted with ethyl acetate, washed with saturated brine, the organic phases were combined, dried over anhydrous sodium sulfate, filtered with suction, concentrated and removed to obtain a white solid (587 mg, 1.76 mmol, 88%). LC-MS (ESI) [M+H] + =335.0.
实施例9Example 9
2'-氟-4'-甲基-5'-((2,2,2-三氟乙基)硫)-[1,1'-联苯]-4-甲腈的制备:
Preparation of 2'-fluoro-4'-methyl-5'-((2,2,2-trifluoroethyl)sulfide)-[1,1'-biphenyl]-4-carbonitrile:
Preparation of 2'-fluoro-4'-methyl-5'-((2,2,2-trifluoroethyl)sulfide)-[1,1'-biphenyl]-4-carbonitrile:
取(4-氟-5-碘-2-甲基苯基)(2,2,2-三氟乙基)硫醚(700mg,2mmol,1.0eq.),加入三苯基膦(50mg,0.2mmol,0.1eq.)和4-氟苯硼酸(441mg,3mmol,1.5eq.),碳酸钾(828mg,6mmol,3.0eq.),醋酸钯(44mg,0.2mmol,0.1eq.)用二氧六环(8mL)溶解,用氮气置换后,于80℃下反应4小时。反应结束后,用乙酸乙酯稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(520mg,1.6mmol,80%)。LC-MS(ESI)[M+H]+=326.0。Take (4-fluoro-5-iodo-2-methylphenyl) (2,2,2-trifluoroethyl) sulfide (700mg, 2mmol, 1.0eq.) and add triphenylphosphine (50mg, 0.2 mmol, 0.1eq.) and 4-fluorophenylboronic acid (441mg, 3mmol, 1.5eq.), potassium carbonate (828mg, 6mmol, 3.0eq.), palladium acetate (44mg, 0.2mmol, 0.1eq.) were treated with dioxane The ring (8 mL) was dissolved, replaced with nitrogen, and reacted at 80° C. for 4 hours. After the reaction was completed, it was diluted with ethyl acetate, washed with saturated brine, the organic phases were combined, dried over anhydrous sodium sulfate, filtered with suction, concentrated and removed to obtain a white solid (520 mg, 1.6 mmol, 80%). LC-MS (ESI) [M+H] + =326.0.
实施例10Example 10
2,4'-二氟-4-甲基-5-((2,2,2-三氟乙基)亚磺酰基)-1,1'-联苯的制备:
Preparation of 2,4'-difluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)-1,1'-biphenyl:
Preparation of 2,4'-difluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)-1,1'-biphenyl:
取(4',6-二氟-4-甲基-[1,1'-联苯]-3-基)(2,2,2-三氟乙基)硫醚(318mg,1mmol,1.0eq.)用二氯甲烷(5mL)溶解,于0℃下加入间氯过氧苯甲酸(346mg,2mmol,2.0eq.)搅拌2小时,TLC监测,原料消失后加入亚硫酸氢钠淬灭反应。用二氯甲烷稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(277mg,0,83mmol,83%)。LC-MS(ESI)[M+H]+=335.0。Take (4',6-difluoro-4-methyl-[1,1'-biphenyl]-3-yl) (2,2,2-trifluoroethyl) sulfide (318mg, 1mmol, 1.0eq .) was dissolved in dichloromethane (5 mL), and m-chloroperoxybenzoic acid (346 mg, 2 mmol, 2.0 eq.) was added at 0°C and stirred for 2 hours. Monitor by TLC. After the raw materials disappeared, sodium bisulfite was added to quench the reaction. Dilute with dichloromethane, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, concentrate and remove, to obtain a white solid (277 mg, 0,83 mmol, 83%). LC-MS (ESI) [M+H] + =335.0.
实施例11
Example 11
4'-氯-2-氟-4-甲基-5-((2,2,2-三氟乙基)亚磺酰基)-1,1'-联苯的制备:
Preparation of 4'-chloro-2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)-1,1'-biphenyl:
Preparation of 4'-chloro-2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)-1,1'-biphenyl:
取(4'-氯-6-氟-4-甲基-[1,1'-联苯]-3-基)(2,2,2-三氟乙基)硫醚(334mg,1mmol,1.0eq.)用二氯甲烷(5mL)溶解,于0℃下加入间氯过氧苯甲酸(346mg,2mmol,2.0eq.)搅拌2小时,TLC监测,原料消失后加入亚硫酸氢钠淬灭反应。用二氯甲烷稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(288mg,0,82mmol,82%)。LC-MS(ESI)[M+H]+=351.0。Take (4'-chloro-6-fluoro-4-methyl-[1,1'-biphenyl]-3-yl) (2,2,2-trifluoroethyl) sulfide (334 mg, 1 mmol, 1.0 eq.) was dissolved in dichloromethane (5 mL), and m-chloroperoxybenzoic acid (346 mg, 2 mmol, 2.0 eq.) was added at 0°C and stirred for 2 hours. Monitor by TLC. After the raw materials disappeared, sodium bisulfite was added to quench the reaction. . Dilute with dichloromethane, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, concentrate and remove, to obtain a white solid (288 mg, 0,82 mmol, 82%). LC-MS (ESI) [M+H] + =351.0.
实施例12Example 12
2'-氟-4'-甲基-5'-((2,2,2-三氟乙基)亚磺酰基)-[1,1'-联苯基]-4-甲腈的合成:
Synthesis of 2'-fluoro-4'-methyl-5'-((2,2,2-trifluoroethyl)sulfinyl)-[1,1'-biphenyl]-4-carbonitrile:
Synthesis of 2'-fluoro-4'-methyl-5'-((2,2,2-trifluoroethyl)sulfinyl)-[1,1'-biphenyl]-4-carbonitrile:
取2'-氟-4'-甲基-5'-((2,2,2-三氟乙基)硫)-[1,1'-联苯]-4-甲腈(325mg,1mmol,1.0eq.)用二氯甲烷(5mL)溶解,于0℃下加入间氯过氧苯甲酸(346mg,2mmol,2.0eq.)搅拌2小时,TLC监测,原料消失后加入亚硫酸氢钠淬灭反应。用二氯甲烷稀释,饱和食盐水洗涤,合并有机相,无水硫酸钠干燥,抽滤,浓缩脱溶,得到白色固体(272mg,0,8mmol,80%)。LC-MS(ESI)[M+H]+=342.0。Take 2'-fluoro-4'-methyl-5'-((2,2,2-trifluoroethyl)sulfide)-[1,1'-biphenyl]-4-carbonitrile (325 mg, 1 mmol, 1.0eq.) was dissolved in dichloromethane (5mL), and m-chloroperoxybenzoic acid (346mg, 2mmol, 2.0eq.) was added at 0°C and stirred for 2 hours. Monitor by TLC. After the raw material disappeared, sodium bisulfite was added to quench it. reaction. Dilute with dichloromethane, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, concentrate and remove, to obtain a white solid (272 mg, 0,8 mmol, 80%). LC-MS (ESI) [M+H] + =342.0.
实施例13Example 13
制剂的制备:Preparation of formulations:
1、悬浮剂:称取20%的式(Ⅰ)化合物、2%FS3000(磷酸酯型阴离子表面活性剂)、3%NS-500LQ(非离子型羟基聚环氧乙烷嵌段共聚物)、0.5%黄原胶、1.5%硅酸镁铝、5%乙二醇、0.5%有机改性硅氧烷消泡剂,去离子水加至100%,制成浆料,进行砂磨后得到产品。1. Suspension agent: Weigh 20% of the compound of formula (I), 2% FS3000 (phosphate anionic surfactant), 3% NS-500LQ (nonionic hydroxyl polyethylene oxide block copolymer), 0.5% xanthan gum, 1.5% magnesium aluminum silicate, 5% ethylene glycol, 0.5% organically modified silicone defoaming agent, deionized water was added to 100% to make a slurry, and the product was obtained after sanding .
2、乳油:称取25%的式(Ⅰ)化合物、15%环己酮、8%乳化剂、20%DMF,二甲苯加至100%,经高剪切乳化机剪切后得到产品。2. Emulsifiable concentrate: Weigh 25% of the compound of formula (I), 15% cyclohexanone, 8% emulsifier, 20% DMF, add xylene to 100%, and obtain the product after being sheared by a high-shear emulsifying machine.
3、可湿性粉剂:称取40%的式(Ⅰ)化合物、7%十二烷基苯磺酸钠、10%木质素磺酸钠,其余为高岭土,经气流粉碎后得到产品。3. Wettable powder: Weigh 40% of the compound of formula (I), 7% sodium dodecylbenzene sulfonate, 10% sodium lignin sulfonate, and the rest is kaolin, and obtain the product after airflow pulverization.
以上均为重量百分比。All the above are weight percentages.
实施例14Example 14
将待测化合物用N,N-二甲基甲酰胺溶解后,然后用含有0.1%吐温80溶液配制成所需浓度的待测液,待用。取二叶期的豌豆苗,接种朱砂叶螨并调查基数,用喷雾塔进行整株喷雾处理,每处理3次重复,处理后置于标准观察室,72小时后调查存活螨数,计算死亡率。After the compound to be tested is dissolved in N,N-dimethylformamide, a solution containing 0.1% Tween 80 is used to prepare a test solution of the required concentration and is ready for use. Take pea seedlings at the two-leaf stage, inoculate them with spider mites and investigate the base number. Use a spray tower to spray the entire plant. Each treatment is repeated three times. After treatment, they are placed in a standard observation room. After 72 hours, the number of surviving mites is investigated and the mortality rate is calculated. .
测试本申请化合物的杀虫活性;并与如下化合物进行杀螨活性的平行测试,具体化合物结构如下:
Test the insecticidal activity of the compounds of this application; and conduct parallel tests on the acaricidal activity with the following compounds. The specific compound structures are as follows:
Test the insecticidal activity of the compounds of this application; and conduct parallel tests on the acaricidal activity with the following compounds. The specific compound structures are as follows:
部分测试结果如下:Some test results are as follows:
药液浓度为2ppm时,When the concentration of the chemical solution is 2ppm,
靶标死亡率在80%以上的化合物有:化合物1-10、12-16、18-24、26、31-33、36,对照化合物CK1-15中的CK1、8、9、10。Compounds with target mortality rates above 80% include: compounds 1-10, 12-16, 18-24, 26, 31-33, 36, and CK1, 8, 9, and 10 among the control compounds CK1-15.
按照以上方法,选取部分化合物与对照化合物CK1、8、9、10进行杀朱砂叶螨活性平行测定,实验结果见下表:According to the above method, some compounds were selected and compared with the control compounds CK1, 8, 9, and 10 for parallel determination of activity against spider mites. The experimental results are shown in the table below:
杀朱砂叶螨活性对照试验:
Controlled test of activity against cinnabar spider mites:
Controlled test of activity against cinnabar spider mites:
上述实施例只是为了说明本发明的技术构思及特点,其目的是在于让本领域内的普通技术人员能够了解本发明的内容并据以实施,并不能以此限制本发明的保护范围。凡是根据本发明内容的实质所作出的等效的变化或修饰,都应涵盖在本发明的保护范围内。
The above embodiments are only for illustrating the technical concepts and characteristics of the present invention. Their purpose is to enable those of ordinary skill in the art to understand the content of the present invention and implement it accordingly. They cannot limit the scope of protection of the present invention. All equivalent changes or modifications made based on the essence of the present invention should be included in the protection scope of the present invention.
Claims (10)
- 一种对位取代的联苯硫醚类化合物,其结构式如式(I)所示:
A para-substituted diphenyl sulfide compound has a structural formula as shown in formula (I):
式(I)中,In formula (I),R1选自H、CN、卤素、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6烷氧基、卤代C1-C6烷氧基、C3-C6环烷基、C3-C6环氧烷基或C3-C6环烷基氧基;R 1 is selected from H, CN, halogen, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;n选自0-2的整数。n is selected from an integer from 0 to 2. - 如权利要求1所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)中,A para-substituted diphenyl sulfide compound as claimed in claim 1, characterized in that, in formula (I),R1选自H、CN、卤素、C1-C4烷基、卤代C1-C4烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C6环烷基、C3-C6环氧烷基或C3-C6环烷基氧基;R 1 is selected from H, CN, halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxy Alkyl or C 3 -C 6 cycloalkyloxy;n选自0-2的整数。n is selected from an integer from 0 to 2.
- 如权利要求2所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)中,A para-substituted diphenyl sulfide compound as claimed in claim 2, characterized in that, in formula (I),R1选自H、CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、CCl3、CHCl2、CH2Cl、CBr3、CH2Br、CHBr2、CH2CF3、CH2CFH2、CH2CHF2、乙烯基、乙炔基、MeO、EtO、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基;R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3. CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CH 2 Br , CHBr 2 , CH 2 CF 3 , CH 2 CFH 2 , CH 2 CHF 2 , vinyl, ethynyl, MeO, EtO, n-PrO , i-PrO, n-BuO, i-BuO, s-BuO, t-BuO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexaneoxy base;n为0或1。n is 0 or 1.
- 如权利要求3所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)中,A para-substituted diphenyl sulfide compound as claimed in claim 3, characterized in that, in formula (I),R1选自H、CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、CCl3、CHCl2、CH2Cl、CBr3、CH2Br、CHBr2、CH2CF3、MeO、EtO、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基。R 1 is selected from H, CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3. CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CH 2 Br, CHBr 2 , CH 2 CF 3 , MeO, EtO, n-PrO, i-PrO, n-BuO, i-BuO, s-BuO , t-BuO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
- 如权利要求1-4中任一项所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)中,A para-substituted diphenyl sulfide compound as claimed in any one of claims 1 to 4, characterized in that, in formula (I),R1选自CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、MeO、EtO、n-PrO、i-PrO、环丙烷基、环戊烷基、环己烷基、环丙烷氧基、环戊烷氧基或环己烷氧基。R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, n-PrO, i-PrO, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
- 如权利要求1所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)中,A para-substituted diphenyl sulfide compound as claimed in claim 1, characterized in that, in formula (I),R1选自CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CHF2、CH2F、CF3、MeO、EtO、环丙烷基;R 1 is selected from CN, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CHF 2 , CH 2 F, CF 3 , MeO, EtO, cyclopropyl;n为0或1。n is 0 or 1.
- 如权利要求1-6中任一项所述的一种对位取代的联苯硫醚类化合物,其特征在于,式(I)结构化合物选自:
A para-substituted diphenyl sulfide compound as claimed in any one of claims 1 to 6, characterized in that the structural compound of formula (I) is selected from:
- 一种杀虫或杀螨组合物,其特征在于,包括杀虫或杀螨有效量的权利要求1-7任一项所述的对位取代的联苯硫醚类化合物中的至少一种;优选的,还包括制剂载体或制剂助剂。An insecticidal or acaricidal composition, characterized by comprising an insecticidal or acaricidal effective amount of at least one of the para-substituted diphenyl sulfide compounds described in any one of claims 1-7; Preferably, formulation carriers or formulation auxiliaries are also included.
- 一种防治害虫或害螨的方法,其特征在于,包括将杀虫或杀螨有效量的权利要求1-7任一项所述的对位取代的联苯硫醚类化合物中的至少一种或如权利要求8所述的杀虫或杀螨组合物使用在害虫或害螨和/或其栖息地上。A method for preventing and controlling pests or harmful mites, characterized by comprising adding an effective amount of insecticidal or acaricidal at least one of the para-substituted diphenyl sulfide compounds described in any one of claims 1-7 Or the insecticidal or acaricidal composition as claimed in claim 8 is used on pests or mites and/or their habitats.
- 如权利要求1-7任一项所述的对位取代的联苯硫醚类化合物中的至少一种或如权利要求8所述的杀虫或杀螨组合物在农业和其它领域中控制害虫或害螨上的用途。 At least one of the para-substituted diphenyl sulfide compounds according to any one of claims 1 to 7 or the insecticidal or acaricidal composition according to claim 8 for controlling pests in agriculture and other fields or use on pest mites.
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US20030069242A1 (en) * | 1998-04-07 | 2003-04-10 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
WO2007034755A1 (en) * | 2005-09-21 | 2007-03-29 | Kumiai Chemical Industry Co., Ltd. | Biphenyl sulfide compounds and insecticides and miticides |
JP2009023910A (en) * | 2007-07-17 | 2009-02-05 | Kumiai Chem Ind Co Ltd | Biphenyl sulfide compound and insecticidal or acaricidal agent |
CN113943238A (en) * | 2020-07-17 | 2022-01-18 | 沈阳中化农药化工研发有限公司 | Substituted diphenyl sulfide compound and application thereof |
CN114957062A (en) * | 2022-07-05 | 2022-08-30 | 海利尔药业集团股份有限公司 | Para-substituted biphenyl thioether compound, composition and application thereof |
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US20030069242A1 (en) * | 1998-04-07 | 2003-04-10 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
WO2007034755A1 (en) * | 2005-09-21 | 2007-03-29 | Kumiai Chemical Industry Co., Ltd. | Biphenyl sulfide compounds and insecticides and miticides |
JP2009023910A (en) * | 2007-07-17 | 2009-02-05 | Kumiai Chem Ind Co Ltd | Biphenyl sulfide compound and insecticidal or acaricidal agent |
CN113943238A (en) * | 2020-07-17 | 2022-01-18 | 沈阳中化农药化工研发有限公司 | Substituted diphenyl sulfide compound and application thereof |
CN114957062A (en) * | 2022-07-05 | 2022-08-30 | 海利尔药业集团股份有限公司 | Para-substituted biphenyl thioether compound, composition and application thereof |
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