CN1681388A - 三环衍生物杀虫剂 - Google Patents
三环衍生物杀虫剂 Download PDFInfo
- Publication number
- CN1681388A CN1681388A CNA038221136A CN03822113A CN1681388A CN 1681388 A CN1681388 A CN 1681388A CN A038221136 A CNA038221136 A CN A038221136A CN 03822113 A CN03822113 A CN 03822113A CN 1681388 A CN1681388 A CN 1681388A
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- CN
- China
- Prior art keywords
- alkyl
- hydrogen
- aryl
- alkoxy
- independently selected
- Prior art date
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- 230000000749 insecticidal effect Effects 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 241000238631 Hexapoda Species 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 102
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 150000002431 hydrogen Chemical class 0.000 claims description 70
- -1 halogenAlkyl Chemical group 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
- 230000000361 pesticidal effect Effects 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 21
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 21
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 20
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 18
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 229910021481 rutherfordium Inorganic materials 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 46
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 43
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- 230000002829 reductive effect Effects 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 238000012360 testing method Methods 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 29
- 239000000575 pesticide Substances 0.000 description 29
- 241000196324 Embryophyta Species 0.000 description 26
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- 239000002917 insecticide Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
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- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 239000004480 active ingredient Substances 0.000 description 11
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- 240000002024 Gossypium herbaceum Species 0.000 description 10
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 239000000417 fungicide Substances 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 241001124076 Aphididae Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000003337 fertilizer Substances 0.000 description 8
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N CHCl3 Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 5
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
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Abstract
已发现一些三环衍生物具有未曾预料的杀虫活性。这些化合物由右式I表示。在此,全面描述R1至R8以及X和Y。还公开了组合物,包含杀虫剂有效量的至少一种式I的化合物,和任选的有效量的至少一种第二化合物,与至少一种适于杀虫剂的载体;还公开了防治控制昆虫的方法,包括将所述组合物应用至昆虫出没或预期会出没的所在地域。
Description
发明领域
本发明一般涉及杀虫剂化合物及其在控制昆虫中的应用。具体而言,本发明涉及杀虫剂的三环衍生物及其农业可接受的盐,这些杀虫剂的组合物,及其在控制昆虫方面的应用。
发明背景
已知昆虫会造成对农田种植的作物的严重损害,导致成百万美元与农作物相关的损失。尽管有许多目昆虫能造成严重的农作物损害,“同翅亚目”昆虫是主要的害虫。同翅亚目包括的昆虫仅列举蚜虫,叶蝉,蝉,粉虱和粉蚧几种为例。同翅目昆虫具有刺穿/吸取口器,它们能通过从维管植物抽取液汁进食。同翅目昆虫造成的危害以各种不同方式出现,除了直接进食造成的损害外。例如,许多种昆虫分泌蜜露,一种粘性废物,它们粘附在昆虫进食和生活的植物上。仅蜜露就会对农作物造成外观损害。烟雾病菌常生长在蜜露上,使得粮食或观赏植物看上去不美观,从而降低其外观和经济价值。一些同翅目昆虫有毒性唾液,在它们进食时注入植物。这些唾液会通过毁损外形造成植物损害,有些情况造成植物死亡。同翅目昆虫还是引起疾病的病原体带菌者。与直接损害不同,它不是由大量疾病带菌昆虫来造成对农作物的可观的损害。
因此,一直需要新的杀虫剂,用于控制例如,同翅目和其他目的昆虫;以及新的杀螨剂,它们是更安全、有效和更低成本,可用于诸如小麦,玉米,大豆,土豆和棉花等作物。为保护作物,要求杀虫剂和杀螨剂控制昆虫和螨但不对作物造成损害,并且对哺乳动物和其他生物体没有不利影响。
其相应文献WO93/00811和美国专利5,366,975公开一种控制无脊椎动物害虫的方法,包括使害虫与一种控制害虫量的药剂接触,通过放射性真蛸胺再吸收抑制试验测定,药剂对苯基乙醇胺再摄取迁移(reuptake transporter)具有明显的抑制活性。在WO93/00811和美国专利5,366,975中提出的组合物中的化合物能抑制真蛸胺迁移体,这类化合物包括三环抗抑郁剂和其药学上可接受的盐,其中列举的三环抗抑郁剂是去甲丙咪嗪,阿米替林,丙米嗪,阿莫沙平,去甲替林,普罗替林,马普替林和多虑平。去甲丙咪嗪和阿米替林特别显示具有对烟草天蛾抗进食活性。还公开了三环止痒盐酸二苯环庚啶也具有对烟草天蛾抗进食活性。
在WO93/00811和美国专利5,366,975中,揭示出一些三环抗抑郁剂和止痒剂对无脊椎动物的农药活性,根据其中提供的有限数据,未建议其他未知其抗抑郁或止痒活性的三环衍生物的杀虫活性,或杀虫活性的程度。
美国专利3,436,397要求一类下式的二苯并环戊-5-二烯噻唑烷酮以专利权:
其中,R选自氢和C1-C4烷基。据报道,二苯并环戊-5-二烯噻唑烷酮具有对horse园线虫的杀幼虫活性,对隐匿管状线虫(Syphacia obvelata)的驱肠虫活性,并可用于治疗哺乳动物的蛲虫感染,对一些革兰氏阳性和革兰氏阴性生物体也具有杀菌活性。
在美国专利3,436,397中没有揭示或建议任何具有杀虫剂活性的化合物。
发明概述
根据本发明,发现一些三环衍生物(下面称作“式I化合物”)和其农业上可接受的盐用于本发明杀虫剂组合物和方法时具有令人惊奇的活性。式I化合物可由下面通式I表示:
其中:
R1至R8,独立地选自:氢、卤素、烷基、环烷基、链烯基、炔基、三烷基甲硅烷基炔基、烷氧基、卤烷基、卤烷氧基、烷硫基、烷基亚硫酰基、烷基磺酰基、卤烷硫基、卤烷基亚硫酰基、卤烷基磺酰基、二烷氨基磺酰基、硝基、氰基、氨基、甲酰基或烷基羰基;
X选自:-CR9R10-,-CR11R12CR13R14-,-CR15=CR16-,-NR17-,-CR18R19NR20-或-CR21=N-;
和
Y选自:-CR22R23-,-CR24R25CR26R27-,-CR28=CR29-,-NR30-,-CR31R32NR33-,-O-,-S-,-S(O)-,-S(O)2-,-CR34R35O-,-CR36R37S-,或-CR38=N-;
其中,
R9和R10独立地选自:氢、烷基或(哌啶-4-基)烷基;
或
R9和R10可以与
一起,或与=CHC2H4NR40R41一起,
其中,
R39,R40和R41独立地选自:氢、烷基、羟烷基、烷氧基烷基、烷硫基烷基、烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基,其中,芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R40和R41可与-C2H4N(CH3)C2H4-一起,形成一个哌嗪环;
U是0或1,
且当u是1时,形成N-氧化物;
n是0,Ra是氢;
或
n是1-8,Ra选自下面基团中的一个或多个:烷基、烷氧基烷基、烷氧基羰基和芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R11选自:氢、烷基、烷氨基烷氧基、二烷氨基烷氧基、N(烷基)(烷氨基烷基)、N(烷基)(二烷氨基烷基)、烷氨基烷基炔基、二烷氨烷基炔基、吗啉基、咪唑啉基、烷基吡咯烷氧基、
其中,
v是0或1,
当v是1时,A是选自下列的桥基:-O-,-S-,-NH-和-CH2-;
u按照上面所述;
R42至R45独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中,芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R43和R44可以与-C5H10-一起形成形成一个哌啶环;
m,p和q是0,Rb,Rc和Rd是氢;
或
m是1-8,p是1-7,q是1-10,Rb,Rc和Rd各自独立地选自一个或多个下面基团:烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中,芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R12,不与R11一起时,R13,R14和R16各自选自:氢、羟基、卤素、烷基、烷氧基、烷基羰基,烷基羰氧基,烷氧基羰基,烷氧基羰氧基、烷氨基羰基、二烷氨基羰基、烷氨基羰氧基(carbonyloxy)、二烷氨基羰氧基、烷氨基磺酰基或二烷氨基磺酰基;
R15选自:
其中,m,u,v,A,Rb和R42如上面所述;
其中:
A,v和u如上面所述;
R46选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基;烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰.基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基,其中的芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R47和R48独立地选自:氢和烷基;
或
R47和R48可与-C5H10-一起形成一个哌啶环,或与-C2H4N(CH3)C2H4-或-C2H4N(C2H4OH)C2H4-一起,形成哌嗪环;
R18和R19独立地选自:氢、烷基、氨基、烷氨基烷基和二烷氨基烷基;
R20选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中的芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R21选自:氢、烷基、
其中:
A,v和u如上面所述;
R49至R52独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基,烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基,杂芳烷基、杂芳基烷氨基,其中的芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R50和R51可以和-C5H10-一起形成一个哌啶环;
r,s和t是0,Re,Rf和Rg是氢,
或
r是1-8,s是1-7,t是1-10,Re,Rf和Rg分别独立地选自下面基团中的一个或多个:烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中的芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R22至R29独立地选自:氢和烷基;
R30选自:氢、烷基、烷氧基烷基、烷氧基羰基;二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中的芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R31和R32独立地选自:氢和烷基;
R33选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中的芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R34至R38独立地选自:氢和烷基;
及其农业上可接受的盐。
本发明还涉及一种组合物,包含杀虫剂有效量的至少一种式I的化合物,和有效量的任选第二化合物,和至少一种适于杀虫剂的载体。
本发明还涉及防治昆虫的方法,该方法包括在要求防治地区,将杀虫剂有效量的上述组合物施用到农作物所在地,或预期会出没的所在地域。
发明详细描述
第一方面,本发明提供杀虫剂组合物,包含杀虫剂、有效量的至少一种式I化合物,和至少一种适于杀虫剂的载体,所述式I化合物如下:
其中:
R1至R8,独立地选自:氢、卤素、烷基、环烷基、链烯基、炔基、三烷基甲硅烷基炔基、烷氧基、卤烷基、卤烷氧基、烷硫基、烷基亚硫酰基、烷基磺酰基、卤烷硫基、卤烷基亚硫酰基、卤烷基磺酰基、二烷氨基磺酰基、硝基、氰基、氨基、甲酰基或烷基羰基;
X选自:-CR9R10-,-CR11R12CR13R14-,-CR15=CR16-,-NR17-,-CR18R19NR20-或-CR21=N-;
和
Y选自:-CR22R23-,-CR24R25CR26R27-,-CR28=CR29-,-NR30-,-CR31R32NR33-,-O-,-S-,-S(O)-,-S(O)2-,-CR34R35O-,-CR36R37S-,或-CR38=N-;
其中,
R9和R10独立地选自:氢、烷基或(哌啶-4-基)烷基;
或
其中,
R39,R40和R41独立地选自:氢、烷基、羟烷基、烷氧基烷基、烷硫基烷基、烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基,其中,芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R40和R41可与-C2H4N(CH3)C2H4-一起,形成一个哌嗪环;
U是0或1,
且当u是1时,形成N-氧化物;
n是0,Ra是氢;
或
n是1-8,Ra选自下面基团中的一个或多个:烷基、烷氧基烷基、烷氧基羰基和芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R11选自:氢、烷基、烷氨基烷氧基、二烷氨基烷氧基、N(烷基)(烷氨基烷基)、N(烷基)(二烷氨基烷基)、烷氨基烷基炔基、二烷氨烷基炔基、吗啉基、咪唑啉基、烷基吡咯烷氧基、
其中,
v是0或1,
当v是1时,A选自下列的桥基:-O-,-S-,-NH-和-CH2-;
u按照上面所述;
R42至R45独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中,芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R43和R44可以与-C5H10-一起形成形成一个哌啶环;
m,p和q是0,Rb,Rc和Rd是氢;
或
m是1-8,p是1-7,q是1-10,Rb,Rc和Rd各自独立地选自一个或多个下述基团:烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中,芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
当R12不与R11一起时,R13,R14和R16各自选自:氢、羟基、卤素、烷基、烷氧基、烷基羰基,烷基羰氧基,烷氧基羰基,烷氧基羰氧基,烷氨基羰基、二烷氨基羰基、烷氨基羰氧基、二烷氨基羰氧基、烷氨基磺酰基或二烷氨基磺酰基;
R15选自:
其中m,u,v,A,Rb和R42如上所述;
R17是氢,烷基,烷氧基烷基,烷氧基羰基,二烷氨基烷基,烷氨基羰基,二烷氨基羰基,烷基磺酰基,芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或-C3H6NR47R48;
其中,
A,v和u如上所述;
R46选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基;烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中芳基杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R47和R48独立地选自:氢和烷基;
或
R47和R48与-C5H10-一起形成一个哌啶环,或与-C2H4N(CH3)C2H4-或-C2H4N(C2H4OH)C2H4-一起形成哌嗪环;
R18和R19独立地选自:氢、烷基、氨基、烷氨基烷基和二烷氨基烷基;
R20选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R21选自:氢、烷基、
其中,
A,v和u如上所述;
R49至R52独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基,烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基,杂芳烷基、杂芳基烷氨基,其中,芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或
R50和R51可与-C5H10-一起形成一个哌啶环;
r,s和t是O,Re,Rf和Rg是氢,
或
r是1-8,s是1-7,t是1-10,Re,Rf和Rg分别独立地选自:一个或多个烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R22至R29独立地选自:氢和烷基;
R30选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R31和R32独立地选自:氢和烷基;
R33选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R34至R38独立地选自:氢和烷基;
及其农业上可接受的盐。
本发明较好的杀虫剂组合物包含式I化合物,其中X是-CR9R10-,Y选自:-O-,-S-,-CR22R23-和-CR34R35O-;
其中,
其中,
R39选自:氢、烷基、羟烷基、烷氧基烷基、烷硫基烷基、烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
而,R22,R23,R34和R35独立地选自:氢和烷基。
本发明其他优选的杀虫剂组合物包含式I的化合物,其中,X是-CR11R12CR13R14-,Y选自:-O-,-S-and-CR22R23-;
其中,
R11选自:
其中,
R42和R45独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基;烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R12选自:氢、羟基、卤素、烷基、烷氧基、烷基羰基、烷基羰氧基,烷氧基羰基,烷氧基羰氧基、烷氨基羰基、二烷氨基羰基、烷氨基羰氧基、二烷氨基羰氧基、烷氨基磺酰基和二烷氨基磺酰基;
R13和R14是氢;
和,
R22和R23独立地选自:氢和烷基。
本发明其他优选的杀虫剂组合物包含式I化合物,其中X是-CR18R19NR20-,Y选自:-O-,-S-和-CR22R23-;
其中,
R20选自:氢、烷基、烷氧基烷基、烷氧基羰基,二烷氨基烷基、烷氨基羰基和二烷氨基羰基;
和,
R22和R23独立地选自:氢和烷基。
本发明还有的优选杀虫剂组合物包含式I的化合物,其中X是-CR21=N-,Y选自:-S-和-CR22R23-;
其中R21是
其中,
R49选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基,烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基,杂芳烷基、杂芳基烷氨基,其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
和,
R22和R23独立地选自:氢和烷基。
当然,本领域技术人员认为,如上面提出的X和Y的一些组合,例如,当X是-CR9R10-,Y是-NR30-时,或X是-NR17-,Y是-CR22R23-时,会导致式I化合物的二重性。化合物这样的二重性超出了本发明的范围。
式I范围内的一些化合物可用于本发明的新颖的杀虫剂组合物,它们是新的和具有新颖性的物质组成。此外,在有些情况下,式I范围内的化合物具有不对称中心,它们可以是光学对映体和非对映异构体。式I范围内的化合物可以两种或多种形式,即以多形体(polymorph)存在,它们的物理和化学性质有明显的差异。式I范围内的化合物还可以互变异构体存在,它们处于平衡。式I范围内的化合物还可具有酸部分或碱部分,它们可以形成农业上可接受的盐或农业上可接受的金属配合物。
本发明包括这样的对映体,多形体,互变异构体,盐和金属配合物的形式使用。农业上可接受的盐和金属配合物包括但不限于,例如,铵盐,有机酸和无机酸的盐,如盐酸,磺酸,乙磺酸,三氟乙酸,甲基苯磺酸,磷酸,葡糖酸,双羟萘酸(pamoic acid)和其他酸盐,以及与例如钠,钾,锂,镁,钙和其他金属的碱金属和碱土金属的配合物。
本发明方法意味着可使杀虫剂有效量的式I化合物存在于昆虫内,以杀灭或防治昆虫。优选的杀虫剂有效量是足以杀灭昆虫的量。通过使昆虫与式I化合物的衍生物接触,使所述化合物存在于昆虫内,这也在本发明范围之内,这些衍生物能在昆虫体内转变为式I的化合物。本发明包括上述化合物的应用,这些化合物称作预-杀虫剂(pre-insecticide)。
第二方面,本发明提供组合物,包含杀虫剂、有效量的至少一种式I的化合物,和任选的有效量的至少一种第二化合物,与至少一种适于杀虫剂的载体。
第三方面,本发明提供控制昆虫的方法,通过将杀虫剂有效量的上述组合物施用到农作物的所在地,农作物例如但不限于,谷类,棉花,蔬菜和水果,或昆虫出没或预期会出没的其他地域。
本发明还包括将上述化合物和组合物用于防治非农业昆虫,例如,噬木(wood termites)白蚁和家白蚁;以及用作药剂物和其组合物。
除非特别指出,在本说明书中使用的取代基术语“烷基”,“链烯基”,“炔基”,“烷氧基”,“链烯基”和“炔基”单独使用或作为较大部分的一部分,包括有至少2个碳原子的直链或支链,对取代基合适的,较好最多至12个碳原子,更好最多至10个碳原子,最好最多至7个碳原子,其中“链烯基”有至少一个碳碳双键,“炔基”有至少一个碳碳三键。术语“芳基”指芳环结构,包括稠环,有4-10个碳原子,例如,苯基和萘基。术语“杂芳基”指芳环结构,包括稠环,有4-10个碳原子,其中环上的一个或多个原子不是碳原子,例如,硫,氧或氮。术语“THF”指四氢呋喃。术语“DMF”指N,N-二甲基甲酰胺。术语“卤素”指氟,溴,碘或氯。术语“室温”常缩写为“RT”,例如,参见化学反应化合物的温度,指在20℃至30℃的温度。术语“杀虫剂组合物”指一种含有能杀灭虫害的杀虫剂的组合物。术语“杀虫剂有效量”指一种含有杀虫剂的组合物以能充分杀灭虫害的比例使用。
式I的三环衍生物可采用本领域技术人员已知的各种方法,由能购得的中间体合成。下面过程1说明了合成式I三环衍生物的通用方法,其中,例如,X是-CR9R10-,Y是-O-或-S-,其中,R9和R10与一起,
反应路线1:
I如上所述和制备,其中Ra是
其中R39是例如-CH3
a)TiCl4/Zn/THF/60℃;b)ClCO2CH2CCl3/CH3CN/CHCl3/回流;c)NaOH/H2O/CH3OH/回流;d)LiAlH4/THF/RT
通过,例如,噻吨-9-酮(Y是-S-),1-甲基-4-哌啶酮,氯化钛(IV)和锌在合适溶剂中反应,得到相应的10-(1-甲基-4-亚哌啶基)苯并[b,e]全氢噻庚因(thiane),式I的化合物。
其他的式I化合物可以多步合成制备,例如,呫顿酮(Y是-O-)与1-苯基甲基-4-哌啶酮,锌和氯化钛(IV)在合适溶剂中反应,如上面所述,产生相应的9-(1-苯基甲基-4-亚哌啶基)呫顿。该呫顿中间体又与2,2,2-三氯乙基氯甲酸酯在合适溶剂中反应,提供相应的9-[1-(2,2,2-三氯乙氧基羰基)-4-亚哌啶基]呫顿(Ia)。中间体(Ia)然后用强碱例如氢氧化钠和合适的醇如甲醇反应,产生相应的9-(1-甲氧基羰基-4-亚哌啶基)呫顿(Ib),它又用例如氢化铝锂在合适溶剂中还原,提供9-(1-甲基-4-亚哌啶基)呫顿,式I的化合物。
下面反应路线2说明合成式I的三环衍生物的通用方法,其中,例如,X是-CR21=N-,Y是-O-或-S-,其中R21是
反应路线2
其中Y是例如-S-或-O-;
R2是1-甲基乙基
其中X可以是例如-CR=N-
其中,r,u,和v是0例如R49是-CH3
a)ClCO2Cl3/EtOAc/回流b)AlCl3/C6H5Cl/80-110℃c)POCl3/C6H5N(C2H5)2 /RTd)1-甲基哌嗪/二甲苯/RT
如反应路线2所示,式I的化合物,例如,其中X是-CR21=N-,Y是-O-或-S-,也可以多步合成进行制备。例如,已知的胺,2-[4-(甲基乙基)苯硫基]苯胺(Y是S)与氯甲酸三氯甲酯在合适溶剂中反应,提供相应的异氰酸酯IIa。中间体Iia再用氯化铝在合适的高沸点溶剂如氯苯中环化,产生相应的环化酮衍生物IIb,例如2-(甲基乙基)-10-二苯并[b,f]-1,4-全氢噻吖庚因(thiazaperhydroepin)-11-酮。然后将中间体IIb用例如氧氯化磷在碱催化剂存在下氯化,得到相应的氯化衍生物IIc。如此制备的氯化物衍生物IIc,例如,11-氯-2-(甲基乙基)二苯并[b,f]1,4-噻吖庚因(thiazepine),通过与合适胺如1-甲基哌嗪反应转变为式I化合物,得到化合物2-(甲基乙基)-11-(4-甲基哌嗪基)二苯并[b,f]1,4-噻吖庚因I。
下面过程3说明合成式I三环衍生物的通用方法,其中,例如,X是CR11R12CR13R14,Y是-O-或-S-,R11和R12代表许多部分。
反应路线3
a)Eatons试剂/RT b)NaBH4/CH3OH/THF/RT c)SOCl2/CH2Cl2/DMF/RT d)1-甲基哌嗪/CHCl3/80℃e)C5H5NBr/n-BuLi/Et2O/-50℃至RT f)CH3I/丙酮/NaBH4/EtOH/RT g)SF3N(C2H5)2/CH2Cl2/RT
如反应路线3所示,合成式I三环衍生物的一般工艺,例如,其中X是-CR11R12CR13R14-,Y是-O-或-S-。也可以多步合成制备例如,一种合适取代的乙酸衍生物,如2-{2-[4-(三氟甲氧基)苯硫基]苯基}乙酸,可用Eaton试剂环化,制得相应的酮衍生物IIIa,例如,8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因(thiepan)-10-酮。中间体IIIa用硼氢化钠在合适溶剂中还原为相应的醇,然后,用亚硫酰氯对醇进行氯化,产生相应的氯衍生物IIIb。制备的氯化物衍生物IIIb,例如,11-氯-2-(三氟甲氧基)-10H,11H-二苯并[b,f]全氢噻庚因,然后通过与合适胺例如1-甲基哌嗪反应转化为式I化合物,提供化合物11-(4-甲基哌嗪基)-2-(三氟甲氧基)-10H,11H-二苯并[b,f]全氢噻庚因(thiepane)I。
或者,酮中间体IIIa可直接与合成的碱反应,提供另外的式I化合物。例如,8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-酮IIIa,如上面所述,可在碱性条件下与含卤素化合物如4-溴吡啶在合适溶剂中反应,提供式I的化合物,例如,10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇。
任何含醇部分的式I化合物还可以进一步反应,制备另一种式I化合物。例如,10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇,如上面所述,烷基卤如碘代甲烷碱性烷基化,任何用还原剂在合适溶剂中碱性还原,产生相应的烷基衍生物,式I的化合物,例如,10-(1-甲基(4-1,2,5,6-四氢吡啶))-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇I。
另一种方法,将含醇部分的式I的化合物,如10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇,如上面所述,可以与例如,三氟化(二乙基氨基)硫在合适溶剂中反应,制得另一种式I化合物,例如,10-氟-10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因。
下面的实施例1至7详细描述了制备式I化合物的方法。
当然,本领域的技术人员认为一种毒药的配方和施用方式会影响在确定应用中的毒药的活性。因此,对农业应用,根据要求的施用方式,本发明的杀虫剂化合物可配制成相对较大粒度(例如,8/16或4/8 US Mesh)的颗粒,水溶性或可水分散的颗粒,粉剂尘,湿性粉剂,可乳化的浓缩物,水性乳液,溶液,或农业上可使用的制剂的任何其他形式。应理解,本说明书中列举的量仅是大约的,和列举量前有“约”一词一样。
这些杀虫剂组合物可以水稀释的喷雾剂,或粉剂,或颗粒施用到要求抑制昆虫的地区。这些制剂可含有最少0.1重量%,0.2重量%或0.5重量%,至最多95重量%或更高的活性组分。
粉剂是可自由流动的混合物,有活性组分与细分散的固体如滑石,天然粘土,硅藻土,粉状物如胡桃壳和棉花籽粉以及其他用作毒药的分散剂和载体的有机物和无机物固体;这些细粉碎的固体的平均粒度小于约50微米。在此有用的典型粉尘制剂是一种含有1.0份或更少的杀虫剂化合物和99.0份的滑石的制剂。
湿性粉剂也是对杀虫剂有用的制剂,是精细粉碎的颗粒,易于分散在水和其他分散剂中。湿性粉剂最终可以干粉尘或水中或其他液体中乳液施用到需要防治昆虫的地区。对湿性粉剂的典型载体包括漂泊土,高岭土,硅石和其他高吸收剂,容易润湿的无机稀释剂。可湿性粉剂通常制备成含有约5-80%活性组分,取决于载体的吸收性,通常还含有少量润湿剂、分散剂或乳化剂,以利于分散。例如,有用的可湿性粉剂制剂含有80.0份杀虫剂化合物,17.9份棕榈粘土和1.0份木素磺酸钠和0.3份磺化脂族聚酯作为润湿剂。在混合罐中经常加入另外的润湿剂,以易于在植物叶上进行分散。
其他对杀虫剂应用有用的制剂有可乳化的浓缩物(EC),它们是均匀的液体组合物,可分散于水或其他分散剂中,而整体由杀虫剂化合物和液体或固体的乳化剂组成,或可含有一种液体载体,如二甲苯,重质芳烃石脑油,异佛尔酮(isphorone),或其他非挥发性有机溶剂。对杀虫剂应用,这些浓缩物可分散在水中或其他液体载体,通常以喷雾剂施用到需要处理的地区。主要活性组分的重量百分比可按照这样的方式变化,施用的组合物中活性组分一般占杀虫剂组合物重量的0.5-95%。
可流动的制剂类似于ECs,不同之处是,活性组分悬浮于一般是水的液体载体中。和ECs一样,可流动制剂包含少量表面活性剂,活性组分含量通常在组合物重量的0.5-95重量%,经常是10-50重量%范围。为能施用,可流动制剂可在水或其他液体中稀释,通常以喷雾剂施用到需要处理的地区。
在农用制剂中使用的典型的润湿剂,分散剂或乳化剂包括但不限于,烷基和烷基芳基磺酸盐,以及硫酸盐和其钠盐;烷基芳基聚醚醇;硫酸化高级醇;聚环氧乙烷;磺化的动物和植物油;磺化石油;多元醇的脂肪酸酯和这类酯的环氧乙烷加成产物;长链硫醇和环氧乙烷的加成产物。许多其他有用的表面活性剂可在市场购得。使用表面活性剂时,通常为组合物重量的1-15重量%。
其他有用的制剂包括活性组分在相对非挥发性溶剂如水、玉米油、煤油、丙二醇或其他合适溶剂中的悬浮液。
对杀虫有用的其他制剂包括活性组分能以要求的浓度完全溶解于一种溶剂如丙酮,烷基化萘,二甲苯或其他有机溶剂的简单溶液。其中含有的毒药为相对粗的颗粒的颗粒制剂,对航空播撒或用于穿透覆盖植物的遮篷特别有用。加压喷雾剂,通常是气溶胶,活性组分以细粉碎形式分散,由于低沸点溶剂的蒸发,还可以使用溶剂载体。水溶性或可水分散的颗粒是自由流动的,无粉尘,易溶于水或水混溶。农民在农田中使用颗粒制剂,可乳化浓缩物,可流动浓缩物,水性乳液,溶液等可用水稀释至活性组分浓度在所述0.1%或0.2%至1.5%或2%的范围。
本发明的杀虫剂活性化合物可与一种或多种第二化合物配制和/或施用。这样的组合能提供一些优点,例如但不限于,对更好防治害虫具有增效作用,降低杀虫剂的施用率,从而对环境和操作者的任何损害最小,防治更广谱的虫害,使农作物对危害植物的毒性安全,提高非害虫种类如哺乳动物和鱼类的耐受性。
第二化合物包括但不限于,其他杀虫剂,植物生长调节剂,肥料,土壤调节剂或其他农用化学品。在施用本发明活性化合物时,无论上单独配制,还是与其他农用化学品配制,当然要使用有效量和浓度的活性化合物;有效量可在如约0.001至约3kg/ha,较好约0.03至约1kg/ha范围变化。对农田应用,在有杀虫剂损失的地方,可采用较高的施用率(如,上述施用率的四倍)。
当本发明的活性杀虫剂化合物与一种或多种第二化合物如其他杀虫剂组合使用时,杀虫剂有如除草剂,除草剂包括但不限于,例如:N-(膦酰基甲基)甘氨酸(″草甘膦″);芳氧基链烷酸类如(2,4-二氯苯氧基)乙酸(″2,4-D″),(4-氯-2-甲基苯氧基)乙酸(″MCPA″),(+/-)-2-(4氯-2-甲基苯氧基)丙酸(“MCPP”);脲类如N,N-二甲基-N’-[4-(1-甲基乙基)苯基]脲(“异丙隆″);咪唑啉酮类如2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-3-吡啶羧酸(″灭草烟″),包含(+/-)-2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-4-甲基苯甲酸和(+/-)2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-5-甲基苯甲酸(″咪草酯″),(+/-)-2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-5-乙基-3-吡啶羧酸(″咪草烟″)和(+/-)-2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-3-喹啉羧酸(″灭草喹″)的反应产物;二苯醚类如5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸(″三氟羧草醚″),5-(2,4-二氯苯氧基)-2-硝基苯甲酸甲酯(″甲羧除草醚″)和5-[2-氯-4-(三氟甲基)苯氧基]-N-(甲磺酰基)-2-硝基苯甲酰胺(″氟黄胺草醚(fomasafen)″);羟基苄腈类如4-羟基-3,5-二碘苄腈(″碘苯腈″)和3,5-二溴-4-羟基苄腈(″溴苯腈″);磺酰基脲如2-[[[[(4氯-6-甲氧基-2-嘧啶基)氨基]羰基]氨基]磺酰基]苯甲酸(″氯嘧黄隆″),2-氯-N-[[(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基]羰基]苯磺酰胺(achlorsulfuron″),2-[[[[[(4,6-二甲氧基-2-嘧啶基)氨基]羰基]氨基]磺酰基]甲基]苯甲酸(″苄嘧黄隆″),2-[[[[(4,6-二甲氧基-2-嘧啶基)氨基]羰基]氨基]磺酰基]-1-甲基-1H-吡唑-4-羧酸(″吡嘧黄隆″),3-[[[[(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基]羰基]氨基]磺酰基]-2-噻吩羧酸(″噻黄隆″)和2-(2-氯乙氧基)-N[[(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)氨基]羰基]苯磺酰胺(″醚苯黄隆″);2-(4-芳氧基苯氧基)链烷酸类如(+/-)-2[4-[(6-氯-2-苯并噁唑基)氧]苯氧基]丙酸(噁唑禾草灵″),(+/-)-2-[4[[5-(三氟甲基)-2-吡啶基]氧]苯氧基]丙酸(″吡氟禾草灵″),(+/-)-2-[4-(6氯-2-喹喔啉基)氧]苯氧基]丙酸(″喹禾灵″)和(+/-)-2-[(2,4-二氯苯氧基)苯氧基]丙酸(″禾草灵″);苯并噻二唑酮类如3-(1-甲基乙基)-1H-1,2,3-苯并噻二唑-4(3H)-酮-2,2-二氧化物(″灭草松″);2-氯N-乙酰苯胺类如N-(丁氧基甲基)-2-氯-N-(2,6-二乙基苯基)乙酰胺(″丁草胺″),2-氯-N-(2-乙基-6-甲基苯基)-N-(2-甲氧基-1-甲基乙基)乙酰胺(“异丙甲草胺”),2-氯-N-(乙氧基甲基)-N-(2-乙基-6-甲基苯基)乙酰胺(“乙草胺”)和(RS)-2-氯-N-(2,4-二甲基-3-噻吩基)-N-(2-甲氧基-1-甲基乙基)乙酰胺(“二甲吩草胺(dimethenamide)”);芳烃羧酸如3,6-二氯-2-甲氧基苯甲酸(″麦草畏″);吡啶氧基乙酸类如[(4-氨基-3,5-二氯-6-氟-2-吡啶基)氧]乙酸(″氟草烟″)和其他除草剂。
当本发明的活性杀虫剂与一种或多种第二化合物,如其他杀虫剂组合使用时,其他杀虫剂包括,例如:有机磷酸酯杀虫剂,如毒死蜱,二嗪农,乐果,马拉松,甲基对硫膦和特丁磷;合成除虫菊酯杀虫剂:如杀灭菊酯,溴氰菊酯,甲氰菊酯,氟氯氰菊酯,氟氰戊菊酯,α-氯氰菊酯,氟氯菊酯,拆解的氯氟氰菊酯,醚菊酯,高氰戊菊酯,四溴菊酯,七氟菊酯,乙氰菊酯,β氟氯氰菊酯和氟酯菊酯;氨基甲酸酯类杀虫剂,如涕灭威,西维因、虫螨威和灭多虫;有机氯杀虫剂,如硫丹,异狄氏剂,七氯和林丹;苯甲酰脲类杀虫剂:如除虫脲,杀虫隆,伏虫隆,定虫隆,氟螨脲,氟铃脲,氟虫脲和氟丙氧脲;和其他杀虫剂,如虫螨咪,四螨嗪,唑螨酯,噻螨酮,艾克敌和吡虫啉。
当本发明的活性杀虫剂化合物与一种或多种第二化合物,如其他杀虫剂组合使用时,其他杀虫剂可如杀真菌剂,杀真菌剂包括:例如苯并咪唑类杀真菌剂,如苯菌灵,多菌灵,涕必灵和甲基托布津;1,2,4-三唑类杀真菌剂,如氟环唑(epoxyconazole),环唑醇,氟硅唑,粉唑醇,丙环唑,戊唑醇,三唑酮和唑菌醇;取代的酰替苯胺类杀真菌剂,如甲霜灵,噁霜灵,杀菌利和烯菌酮;有机磷杀菌剂,如藻菌磷,异稻瘟净,定菌磷,克瘟散和甲基立枯磷;吗啉类杀真菌剂,如丁苯吗啉,克啉菌和吗菌灵;其他内吸杀真菌剂,如异嘧菌醇,烯菌灵,丙氯灵,三环唑和嗪氨灵;二硫代氨基甲酸酯类杀真菌剂,如代森锰锌,代森锰,甲基代森锌,代森锌和福美锌;非内吸杀真菌剂,如百菌清,抑菌灵,二噻农和异丙定,克菌丹,敌螨普,多果定,氟啶胺,双瓜辛胺,五氯硝基苯,戊菌隆,五氯硝基苯,tricylamide和有效霉素;无机杀真菌剂,如铜和硫产品和其他杀真菌剂。
当本发明的活性杀虫剂化合物与一种或多种第二化合物,如其他杀虫剂组合使用时,其他杀虫剂是如杀线虫剂,杀线虫剂包括,例如:虫螨威,丁硫克百威,turbufos,涕灭威(aldecarb),灭克磷,虫胺磷(fenamphos),甲氨叉威,氯唑磷,硫线磷和其他杀线虫剂。
当本发明的活性杀虫剂化合物与一种或多种第二化合物,如其他杀虫剂组合使用时,其他杀虫剂是植物生长调节剂,植物生长调节剂包括,例如:马拉酰肼,矮壮素阳离子,乙烯利,九二0(gibberellin),比克,脱叶灵(thidiazon),抗倒胺,抑芽唑,多效唑,烯效唑(unaconazol),DCPA,调环酸,抗倒酯和其他植物生长调节剂。
土壤调节剂是加入到土壤时能促进对植物有效生长有益的各种因素的物质。土壤调节剂用于降低土壤压实,促进和提高排水效力,促进土壤中植物营养含量最佳,促进更好地加入杀虫剂和肥料。当本发明的活性杀虫剂化合物与一种或多种第二化合物,如其他杀虫剂组合使用时,其他杀虫剂是如土壤调节剂,土壤调节剂包括有机物,如腐殖质,能促进土壤中阳离子植物营养的保持;阳离子营养混合物,如钙,镁,碳酸钾,钠和氢配合物;或微生物组合物,能促进有利于植物生长的土壤条件。这样的微生物组合物包括,例如,杆状菌,假单孢菌,固氮菌,azospirillum,根瘤菌和土壤自生藻青菌。
肥料是植物的食物来源,通常含有氮,磷和钾。当本发明的活性杀虫剂化合物与一种或多种第二化合物,如其他物质组合使用时,其他物质是如肥料,肥料包括氮肥,如硫酸铵,硝酸铵和骨粉;磷酸盐肥料,如过磷酸盐,三元过磷酸盐,硫酸铵和硫酸二铵;钾肥,如氯化钾,硫酸钾和硝酸钾,和其他肥料。
下面的实施例进一步说明本发明,但这些实施例不以任何方式构成对本发明范围的限制。将这些实施例组织起来可提供合成本发明式I化合物的方法,列出这样合成的物质和表明这类化合物的有效性的一些生物数据。
实施例1
以此实施例说明制备10-(1-甲基-4-亚哌啶基)苯并[b,e]全氢噻庚因(thiane)(下表中的化合物2)的方法
在氮保护下,将45mL搅拌的THF在冰水浴中冷却。用注射器在其中加入8mL(0.008mole)氯化钛(IV)(1.0M的甲苯溶液),然后在5分钟内,分两部分加入1.0克(0.016mole)锌。之后,搅拌反应混合物10分钟,然后在10分钟内,滴加0.76克(0.0036mole)噻吨-9-酮和0.56克(0.005mole)1-甲基-4-哌啶酮在20mL THF中的溶液。添加完毕后,搅拌反应混合物10分钟后,加热至60℃,搅拌约20小时。之后,冷却反应混合物,并将其倒入50mL 10%碳酸钾水溶液。搅拌混合物约20分钟后,加入50mL乙酸乙酯,混合物再搅拌20分钟。通过硅藻土垫过滤混合物,硅藻土垫用50mL乙酸乙酯洗涤。分离从洗涤液和滤液合并的乙酸乙酯,水相用20mL乙酸乙酯萃取。合并的乙酸乙酯部分用饱和碳酸氢钠水溶液洗涤,用硫酸钠干燥。过滤混合物,减压下浓缩滤液得固体残余物。该残余物用氧化铝(中性活性III)上柱色谱纯化,使用庚烷和乙酸乙酯混合物作为洗脱液。合并合适馏分,减压下浓缩,得0.25克化合物2。NMR谱与提出的结构一致。
实施例2
以此实施例说明制备9-(1-甲基-4-亚哌啶基)呫顿(下表中化合物8)的方法
步骤A
合成9-(1-苯基甲基-4-亚哌啶基)呫顿作为中间体
此化合物按照类似于实施例1的方式,通过0.78克(0.004mole)占吨酮,0.95克(0.005mole)1-苯基甲基-4-哌啶酮,1.6克(0.024mole)锌和12mL(0.012mole)氯化钛(IV)(1.0M甲苯溶液)在70mL THF中反应制备。目标化合物的产量为1.4克。NMR谱与提出的结构一致。
步骤B
合成9-[1-(2,2,2-三氯乙氧基羰基)-4-亚哌啶基]呫顿为中间体
在氮气氛下,搅拌0.7克(0.002mole)9-(1-苯基甲基-4-亚哌啶基)呫顿在50mL 1∶2氯仿∶乙腈的溶液,通过注射器一次加入0.85克(0.004mole)2,2,2-氯甲酸三氯乙酯。添加完毕后,反应混合物加热至回流,并搅拌1小时,然后反应混合物冷却至室温,并搅拌约18小时。之后,将反应混合物倒入50mL水中,用两份40mL乙酸乙酯萃取。合并的萃取液用饱和氯化钠水溶液洗涤,用硫酸钠干燥。混合物过滤,滤液减压下浓缩为残余油。将此油溶解在20mL甲醇中,在其中加入5mL水。混合物在冰水浴中冷却,形成固体沉淀物。过滤收集此固体,真空干燥,得0.73克标题化合物,mp 132-134℃。NMR谱与提出的结构一致。
步骤C
合成9-(1-甲氧基羰基-4-亚哌啶基)呫顿作为中间体
0.6克(0.0013mole)9-[1-(2,2,2-三氯乙氧基羰基)-4-亚哌啶基]呫顿,0.25克(0.0062mole)氢氧化钠和2mL水在20mL甲醇的搅拌溶液加热至回流,并搅拌6小时。之后,反应混合物冷却至室温,并搅拌约18小时。将反应混合物减压下浓缩,除去大部分甲醇,加入饱和碳酸氢钠水溶液。混合物用两份20mL乙酸乙酯萃取,合并的萃取液用硫酸钠干燥。过滤混合物,减压下浓缩滤液得油状残余物。残余物通过二氧化硅上柱色谱纯化,使用5∶1庚烷∶乙酸乙酯作为洗脱液。合并合适的馏分,减压下浓缩,得0.28克标题化合物。NMR谱与提出的结构一致。
注:在上面制备例步骤C中的The需要的中间体是9-(4-亚哌啶基)呫顿。
步骤D
合成化合物8
在氮气氛下,搅拌0.28克(0.0008mole)9-(1-甲氧基羰基-4-亚哌啶基)呫顿在20mL THF的溶液,在10分钟内,用注射器加入3mL氢化铝锂(1.0M在THF中)。之后,将反应混合物加热至40℃,并搅拌2小时。冷却反应混合物,一次加入20mL 0.5N氢氧化钠水溶液。混合物用两份40mL乙酸乙酯萃取,合并的萃取液用20mL饱和碳酸氢钠水溶液洗涤。萃取液用硫酸钠干燥,并过滤。滤液减压下浓缩,产生0.2克化合物5。NMR谱与提出的结构一致。
实施例3
此实施例说明制备2-(甲基乙基)-11-(4-甲基哌嗪基)二苯并[b,f]1,4-噻吖庚因(下表化合物193)的方法
步骤A
合成2-[4-(甲基乙基)苯硫基]苯异氰酸酯作为中间体
在氮气氛下,搅拌1.2克(0.0049mole)2-[4-(甲基乙基)苯硫基]苯基胺(已知化合物)在60mL乙酸乙酯的溶液,用吸液管一次加入2.2克(0.011mole)三氯甲基chlorooate。添加完毕后,反应混合物加热至回流,并搅拌3小时。之后,反应混合物冷却,减压下浓缩为残余物。残余物进一步真空干燥,产生1.5克标题化合物。NMR谱与提出的结构一致。
步骤B
合成2-(甲基乙基)-10-二苯并[b,f]-1,4-全氢噻吖庚因-11-酮作为中间体
在氮气氛下,将1.0克(0.0075mole)氯化铝在5mL氯苯的混合物搅拌加热至80℃,在1分钟内滴加1.4克(0.0052mole)2-[4-(甲基乙基)苯硫基]苯异氰酸酯在1mL氯苯中的溶液。添加完毕后,反应混合物加热至110℃,并搅拌2小时。之后,反应混合物冷却,将其倒入水中。混合物用两份40mL乙酸乙酯萃取,合并萃取液。合并的萃取液用饱和氯化钠水溶液洗涤,用硫酸钠干燥,过滤;滤液减压下浓缩为残余物。残余物通过二氧化硅上柱色谱纯化,使用5∶1和3∶1的庚烷∶乙酸乙酯的混合物作为洗脱液。合并合适的馏分,减压下浓缩,产生0.65克标题化合物。NMR谱与提出的结构一致。
步骤C
合成11-氯-2-(甲基乙基)二苯并[b,f]1,4-噻吖庚因作为中间体
在氮气氛下,搅拌0.62克(0.0023mole)2-(甲基乙基)-10-二苯并[b,f]-1,4-全氢噻吖庚因-11-酮在10mL氧氯化磷的溶液,滴加5滴二乙基苯基胺。添加完毕后,将反应混合物加热至回流,并搅拌3.5小时。反应混合物减压下浓缩,除去大部分氧氯化磷,将残余物倒入50mL冰水中。混合物用三份30mL乙醚萃取。合并的萃取液用饱和氯化钠水溶液洗涤,用硫酸钠干燥,过滤;滤液减压下浓缩,得0.55克标题化合物。NMR谱与提出的结构一致。
步骤D
合成化合物193
在氮气氛下,将0.24克(0.0008mole)11-氯-2-(甲基乙基)二苯并[b,f]1,4-噻吖庚因和0.4mL(0.0036mole)1-甲基哌嗪在25mL二甲苯中的搅拌溶液加热至回流,并搅拌2小时。之后,冷却至室温反应混合物,将其倒入25mL乙醚中。混合物用三份20mL 3N盐酸水溶液萃取。合并含水萃取液,用20mL乙醚洗涤,用10%碳酸钾水溶液使其为碱性;然后用三份20mL乙醚萃取。合并醚萃取液,用硫酸钠干燥,过滤,减压下浓缩得残余物。残余物通过二氧化硅上柱色谱纯化,使用二氯甲烷,1%甲醇的二氯甲烷溶液和3%甲醇的二氯甲烷溶液作为洗脱液。合并合适的馏分,减压下浓缩,得0.21克化合物193。NMR谱与提出的结构一致。
实施例4
此实施例说明制备11-(4-甲基哌嗪基)-2-(三氟甲氧基)-10H,11H-二苯并[b,f]全氢噻庚因(thiopane)(下表化合物106)方法
步骤A
合成2-{2-[4-(三氟甲氧基)苯硫基]苯基}乙酸作为中间体
搅拌26.2克(0.47mole)氢氧化钾和1.1克(0.018mole)铜粉(催化剂)在200mL水中的混合物,加入30.6克(0.117mole)2-碘苯基乙酸和22.7克(0.117mole)4-三氟甲氧基苯酚。添加完毕后,加热反应混合物至回流,并搅拌约18小时。之后,将反应混合物冷却至室温,过滤。将滤液倒入至500mL 10%盐酸水溶液中,对混合物用三份250mL乙酸乙酯萃取。合并的萃取液用饱和氯化钠水溶液洗涤,用硫酸钠干燥,过滤并减压浓缩,得39.6克标题化合物。
步骤B
合成8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-酮作为中间体
搅拌10.0克(0.0304mole)2-{2-[4-(三氟甲氧基)苯硫基]苯基}乙酸在75mLEatons试剂的混合物18小时,在此期间得到溶液。之后,将反应混合物倒入冰水中,用四份150mL乙酸乙酯萃取。合并的萃取液用一份碳酸氢钠稀水溶液,一份饱和氯化钠水溶液洗涤。有机层用硫酸钠干燥,过滤,减压下浓缩得残余物。残余物通过二氧化硅上柱色谱纯化,使用1∶2乙酸乙酯∶己烷作为洗脱液。合并合适的馏分,减压下浓缩,得4.0克标题化合物。NMR谱与提出的结构一致。
步骤C
合成11-氯-2-(三氟甲氧基)-10H,11H-二苯并[b,f]全氢噻庚因作为中间体
搅拌2.3克(0.0073mole)8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-酮在5mL THF和30mL甲醇的混合物中的溶液,加入0.4克硼氢化钠。反应混合物于室温搅拌2小时。之后,将反应混合物倒入100mL 10%盐酸水溶液,在其中加入300mL饱和氯化钠水溶液。混合物用三份100mL乙酸乙酯萃取。合并的萃取液用硫酸钠干燥,过滤,减压下浓缩滤液得残余物。进一步干燥残余物,将其溶解在50mL二氯甲烷,减压下浓缩混合物得残余物。该干燥过程再重复两次,得干残余物。将该残余物再次溶解在50mL二氯甲烷,加入3mL亚硫酰氯。反应混合物于室温搅拌2.5小时。之后,反应混合物减压下浓缩,得2.0克标题化合物。
步骤D
合成化合物106
将1.0克(0.0030mole)11-氯-2-(三氟甲氧基)-10H,11H-二苯并[b,f]全氢噻庚因的溶液溶解在5mL氯仿中,置于一密封管中,随后加入1.2克(0.0119mole)1-甲基哌嗪。然后密封该管,将管内容物于80℃加热18小时。取出反应混合物,通过二氧化硅上柱色谱纯化,使用二氯甲烷,然后是乙酸乙酯作为洗脱液。合并合适的馏分,减压下浓缩,产生0.6克化合物106。NMR谱与提出的结构一致。
实施例5
此实施例说明制备10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇(下表化合物61)方法
将1.0克(0.0051mole)4-溴吡啶盐酸盐与20mL饱和碳酸氢钠水溶液搅拌20分钟。用两份20mL二氯甲烷萃取混合物。合并的萃取液用硫酸钠干燥,过滤,减压下浓缩,得0.5克游离吡啶物。
在氮气氛下,将约0.4克游离吡啶物溶解在40mL乙醚中,在干冰-乙腈浴中冷却至约-50℃。用注射器在此冷溶液中加入1.0mL(0.0025mole)2.5M正丁基锂(己烷中),同时保持反应混合物低于或等于-45℃。添加完毕后,将反应混合物于-50℃搅拌30分钟,然后,一次加入混溶0.6克(0.0020mole)8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-酮(在实施例4步骤B制备)。添加完毕后,反应混合物回热至室温,并搅拌1.5小时。之后,将反应混合物倒入50mL水中,分出有机层。水层用两份30mL乙醚萃取。合并萃取液和有机层,用饱和氯化钠水溶液洗涤。然后,合并液用硫酸钠干燥,过滤,滤液减压下浓缩得残余物。残余物通过二氧化硅上柱色谱纯化,使用3∶1庚烷∶乙酸乙酯,然后用1∶1庚烷∶乙酸乙酯作为洗脱液。合并合适的馏分,减压下浓缩,得0.6克化合物61。NMR谱与提出的结构一致。重复该反应数次。
实施例6
此实施例说明制备10-(1-甲基(4-1,2,5,6-四氢吡啶))-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇(下表化合物215)方法
将0.55克(0.0014mole)10-(4-吡啶)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇(实施例5中制备)和0.43克(0.0030mole)碘甲烷在60mL丙酮中的溶液在一塞好的反应器中搅拌约18小时。之后,反应混合物通过薄层色谱(TLC)分析,表明有些未反应的全氢噻庚因-10-醇。在反应混合物中再加入0.43克碘甲烷,再继续搅拌24小时。之后,反应混合物减压下浓缩为残余固体,用石油醚研制,并干燥。将固体溶解在40mL乙醇中,搅拌,加入0.45克(0.012mole)氢硼化钠。三小时内加完至反应混合物。之后,将反应混合物倒入75mL 1%碳酸氢钠水溶液。混合物用三份20mL乙酸乙酯萃取。合并的萃取液用饱和氯化钠水溶液洗涤,用硫酸钠干燥,过滤和减压下浓缩,得0.40克化合物215。NMR谱与提出的结构一致。
实施例7
此实施例说明制备10-氟-10-(4-吡啶基)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因(下表化合物216)方法
在氮气氛下,搅拌0.12克(0.0003mole)10-(4-吡啶基)-8-(三氟甲氧基)-11H-二苯并[b,f]全氢噻庚因-10-醇(实施例5制备)在10mL二氯甲烷中的溶液,用注射器加入0.12克(0.0008mole)(二乙氨基)三氟化硫。添加完毕后,将反应混合物搅拌20分钟,然后将其倒入30mL碳酸氢钠稀水溶液中。分出有机层,水层用25mL二氯甲烷萃取。合并萃取液和有机层,用饱和氯化钠水溶液洗涤。合并物用硫酸钠干燥,过滤,滤液减压下浓缩为残余物。残余物通过氧化铝上柱色谱纯化(中性,活性III),使用5∶1庚烷∶乙酸乙酯作为洗脱液。合并合适的馏分,减压下浓缩,得0.1克化合物216。NMR谱与提出的结构一致。
本领域技术人员皆知,如本发明式I化合物的化合物可任选含有光学活性和外消旋形式。此外,已知如式I化合物的化合物可任选含有立体异构体形式,互变异构体形式和/或显示多形性。应理解,本发明包括任何外消旋,光学活性,多形体,互变异构体或立体异构体形式,或它们的混合物。应注意,本领域人员皆知如何制备光学活性形式,例如通过拆分外消旋混合物,通过由光学活性中间体合成。
下表列出对本发明有用的式I化合物的另一些例子:
表1
杀虫剂吩噻嗪,吩噁嗪,二氢吩嗪,
二苯并噻庚因(dibenothiepin),二苯并噁庚因(dibenooxepin),
二苯并吖庚因(dibenoazepine)
其中X是-CR9R10-,R9和R10与
一切,其中u是0,Ra是氢,R1和R5至R8是氢:
化合物 | Y | R30 | R2 | R3 | R4 | R39 | Ra | n |
1 | S | ---- | H | H | H | H | H | 0 |
2 | S | ---- | H | H | H | CH3 | H | 0 |
3 | S | ---- | H | H | H | CH(CH3)2 | H | 0 |
4 | S | ---- | Cl | H | H | CH3 | H | 0 |
5 | S | ---- | CF3 | H | H | CH3 | H | 0 |
6 | S | ---- | SCH3 | H | H | CH3 | H | 0 |
7 | S | ---- | H | H | H | CH2C≡N | H | 0 |
8 | O | ---- | H | H | H | CH3 | H | 0 |
9 | O | ---- | F | H | H | CH3 | H | 0 |
10 | O | ---- | H | F | H | CH3 | H | 0 |
11 | O | ---- | H | H | F | CH3 | H | 0 |
12 | O | ---- | C2H5 | H | H | CH3 | H | 0 |
13 | O | ---- | OC2H5 | H | H | CH3 | H | 0 |
14 | O | ---- | C2H4OCH3 | H | H | CH3 | H | 0 |
化合物 | Y | R30 | R2 | R3 | R4 | R39 | Ra | n |
1516171819202122232425 | OOOOOOOONR30NR30NR30 | --------------------------------HCH3CH3 | CF3HClCF3SCH3HHHHHCF3 | HOCF3HHHHHHHHH | HHHHHHHHHHH | CH3CH3CH2PhCH2PhCH2PhC2H4CO2C2H5CH3CH3CH3CH3CH3 | HHHHHH2-CH33-CH3HHH | 00000011000 |
其中,X是-CR9R10-;Y是-CR34R35O-,R1,R3,R4,R5,R7,R8,R34,R35是氢,n是0,Ra是氢:
*其中u是0
其中,X是-CR9R10-;Y是-CR36R37S-,R1至R5,R7,R8,R36和R37是氢,n是0,Ra是氢:
其中u是0
其中,X是-CR9R10-,Y是-CR31R32NR33-,其中R1至R8,R31和R32是氢,n是0,Ra是氢:
其中u是0
其中,X是-CR9R10-;Y是-CR38=N-,R1,R3至R8,R38是氢,n是0,Ra是氢:
*其中u是0
其中,X是-CR11R12CR13R14-;其中R1,R3至R8,R13和R14是氢,n和m是0,Ra和Rb是氢,当注明时,v是1,则A是-O-:
*其中,u是0
**其中,v是1
其中,X是-CR11R12CR13R14-;其中,R12,R13和R14是氢,和
R11是:
其中,v是0;m是0,Rb是氢,R42是-CH3;除非特别注明u是0:
化合物 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | Y | R22 | R23 | R30 | |
63 | H | H | H | H | H | H | H | H | O | ---- | ---- | ---- | |
64 | H | Cl | H | H | H | H | H | H | O | ---- | ---- | ---- | |
65 | H | Br | H | H | H | H | H | H | O | ---- | ---- | ---- | |
66 | H | F | H | H | H | H | H | H | O | ---- | ---- | ---- | |
67 | H | I | H | H | H | H | H | H | O | ---- | ---- | ---- | |
68 | H | CH3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
69 | H | CF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
70 | H | SCH3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
71 | H | OCF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
72a | H | OCF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
73 | H | H | OCF3 | H | H | H | H | H | O | ---- | ---- | ---- | |
74a | H | H | OCF3 | H | H | H | H | H | O | ---- | ---- | ---- | |
75 | H | SCF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
76 | H | S(O)CF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
77 | H | S(O)2CF3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
78 | H | -CH=CH2 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
79 | H | -C≡CH | H | H | H | H | H | H | O | ---- | ---- | ---- | |
80 | H | -C≡CSi(CH3)3 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
81 | H | NO2 | H | H | H | H | H | H | O | ---- | ---- | ---- | |
82 | H | Cl | Cl | H | H | H | H | H | O | ---- | ---- | ---- | |
83 | H | Cl | H | Cl | H | H | H | H | O | ---- | ---- | ---- | |
84 | H | Cl | F | H | H | H | H | H | O | ---- | ---- | ---- | |
85 | H | Cl | H | F | H | H | H | H | O | ---- | ---- | ---- | |
86 | H | F | Cl | H | H | H | H | H | O | ---- | ---- | ---- | |
87 | H | F | H | Cl | H | H | H | H | O | ---- | ---- | ---- | |
88 | H | Br | H | F | H | H | H | H | O | ---- | ---- | ---- | |
89 | H | Br | H | CH3 | H | H | H | H | O | ---- | ---- | ---- | |
902 | H | H | H | H | H | H | H | H | S | ---- | ---- | ---- |
化合物 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | Y | R22 | R23 | R30 | |
912 | H | H | Cl | H | H | H | H | H | S | ---- | ---- | ---- | |
92 | H | H | Cl | H | H | Cl | H | H | S | ---- | ---- | ---- | |
93 | F | H | H | H | H | H | H | H | S | ---- | ---- | ---- | |
94 | H | H | H | F | H | H | H | H | S | ---- | ---- | ---- | |
95 | H | Cl | F | H | H | H | H | H | S | ---- | ---- | ---- | |
968 | H | Cl | H | F | H | H | H | H | S | ---- | ---- | ---- | |
97 | F | H | H | F | H | H | H | H | S | ---- | ---- | ---- | |
989 | H | C2H5 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
99 | H | C(CH3)3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
100 | H | OCH3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
101 | H | H | OCH3 | H | H | H | H | H | S | ---- | ---- | ---- | |
102 | H | H | H | OCH3 | H | H | H | H | S | ---- | ---- | ---- | |
1032 | H | SCH3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
1048 | H | SC2H5 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
105 | H | CF3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
106 | H | OCF3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
107a | H | OCF3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
108 | H | OCF3 | H | H | H | H | F | H | S | ---- | ---- | ---- | |
109 | H | OCF2CHF2 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
1102 | H | H | Cl | Cl | H | H | H | H | S | ---- | ---- | ---- | |
111 | H | CH3 | F | H | H | H | H | H | S | ---- | ---- | ---- | |
112 | c-C3H5 | H | H | H | H | H | H | H | S | ---- | ---- | ---- | |
113 | H | c-C5H9 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
114 | H | NH2 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
115 | H | C(=O)CH3 | H | H | H | H | H | H | S | ---- | ---- | ---- | |
116 | H | H | H | H | F | H | H | H | S | ---- | ---- | ---- | |
11710 | H | H | H | H | F | H | H | H | S | ---- | ---- | ---- | |
118 | H | H | H | H | H | F | H | H | S | ---- | ---- | ---- | |
119 | H | H | H | H | H | H | F | H | S | ---- | ---- | ---- | |
120 | H | H | H | H | H | H | H | F | S | ---- | ---- | ---- | |
121 | H | Cl | H | H | H | F | H | H | S | ---- | ---- | ---- | |
122 | H | SCH3 | H | H | H | F | H | H | S | ---- | ---- | ---- | |
123 | H | SCH3 | H | H | H | H | F | H | S | ---- | ---- | ---- | |
124 | H | SC2H5 | H | H | H | H | F | H | S | ---- | ---- | ---- | |
1254 | H | CF3 | H | H | H | H | F | H | S | ---- | ---- | ---- |
化合物 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | Y | R22 | R23 | R30 |
126 | H | OCF3 | H | H | H | H | F | H | S | ---- | ---- | ---- |
127 | H | CH(CH3)2 | H | H | H | H | F | H | S | ---- | ---- | ---- |
1282 | H | CH(CH3)2 | H | H | H | H | F | H | S | ---- | ---- | ---- |
129 | H | CH(CH3)2 | H | H | H | H | F | H | S(O) | ---- | ---- | ---- |
130 | H | H | H | H | H | H | H | H | CR22R23 | H | H | ---- |
131 | H | OCF3 | H | H | H | H | H | H | CR22R23 | H | H | ---- |
132 | H | H | H | H | H | H | H | H | NR30 | ---- | ---- | H |
133 | H | F | H | H | H | H | H | H | NR30 | ---- | ---- | H |
134 | H | CF3 | H | H | H | H | H | H | NR30 | ---- | ---- | H |
135 | H | SCH3 | H | H | H | H | H | H | NR30 | ---- | ---- | H |
136 | H | OCF3 | H | H | H | H | H | H | NR30 | ---- | ---- | H |
137 | H | H | H | H | H | H | H | H | NR30 | ---- | ---- | CH3 |
au是1,形成N-氧化物
其中,X是-CR11R12CR13R14-;其中,R12,R13和R14是氢和
R11是:
其中,v是0;m是0 and Rb是氢,R3,R4和R8是氢,除非特别注明u是0:
化合物 | R1 | R2 | R5 | R6 | R7 | Y | R42 |
138 | H | OCF3 | H | H | H | O | H |
139 | H | OCF3 | H | H | H | O | C2H5 |
140 | H | OCF3 | H | H | H | O | C(=O)CH3 |
141 | H | SCH3 | H | H | H | O | 2-哌啶基乙基氨基 |
142 | H | H | F | H | H | S | C2H5 |
143 | H | OCF3 | H | H | H | S | H |
144 | H | OCF3 | H | H | H | S | C2H5 |
145 | H | OCF3 | H | H | H | S | CH2CH=CH |
146 | H | SCH3 | H | H | H | S | C2H5 |
14710 | H | H | F | H | H | S | C2H5 |
148 | H | H | H | H | H | S | C≡N |
1499 | H | Cl | H | H | H | S | C≡N |
150 | H | CF3 | H | H | F | S | C2H4OH |
151 | H | S(O)CH3 | H | H | F | S | C2H4OH |
152 | H | OCH3 | H | H | H | S | C3H6OH |
1534 | H | SCH3 | H | H | F | S | C3H6OH |
1542 | H | Cl | H | H | H | S | C2H4OC2H5 |
155 | H | SCH3 | H | H | H | S | CH2CH(OH)C2H5 |
156 | H | OCF3 | H | H | H | S | C2H4OCH3 |
157 | H | OCF3 | H | H | H | S | C2H4OC2H5 |
158 | H | SCH3 | H | H | H | S | C2H4O苯基 |
1592 | H | H | H | Cl | H | S | C2H4O苯基 |
160 | H | Cl | H | H | H | S | C2H4SCH3 |
1614 | H | CH(CH3)2 | H | H | F | S | 2-(4-氟苯氧基)乙基 |
162 | H | OCF3 | H | H | H | S | C(=O)CH3 |
1639 | H | SCH3 | H | H | H | S | C(=O)CH3 |
164 | H | OCF3 | H | H | H | S | CO2CH3 |
165 | H | OCF3 | H | H | H | S | CH2CO2C2H5 |
166 | H | OCF3 | H | H | H | S | C3H6CO2C2H5 |
1674 | H | OCH3 | H | H | H | S | C3H6CO2C4H9 |
168 | H | CH(CH3)2 | H | H | F | S | 3-(4-氟苯基羰基)内基 |
1694 | H | CH(CH3)2 | H | H | F | S | 3-(4-氟苯基羰基)丙基 |
170 | H | SCH3 | H | H | H | S | 苯基甲基 |
1712 | H | Cl | H | H | F | S | 4-氟苯基甲基 |
172 | H | SCH3 | H | H | H | S | 吡啶-4-基 |
173 | H | SCH3 | H | H | H | S | 吡啶-4-基甲基 |
其中,X是-CR11R12CR13R14-;Y是-S-,其中,R1,R3至R8,R12至R14是氢,和
R11是:
其中,v是0;pis 0,Rc是氢:
化合物 | R2 | R43 | R44 |
174 | H | H | CH3 |
175 | H | CH3 | CH3 |
176 | SCH3 | CH3 | CH3 |
177 | CF3 | CH3 | CH3 |
178 | OCF3 | CH3 | CH3 |
179 | -C5H10- |
其中,X是-CR11R12CR13R14-;其中,R1,R3至R8,R12至R14是氢,和
R11是:
其中,v是0;qis 0,Rd是氢,u是0:
化合物 | Y | R2 | R45 |
180181182183184185186 | SSSSSSO | HHHSCH3CF3OCF3OCF3 | HCH3C2H5CH3CH3CH3CH3 |
其中,X是-CR18R19NR20-,其中,R19和R20是氢;
化合物 | R1至R8 | Y | R18 |
187 | H | S | CH2NHCH3 |
其中,X是-CR21=N-;
化合物 | R1 | R2 | R3至R8 | Y | R21 |
188 | H | Cl | H | S | 1-甲基吡咯烷-3-基氧 |
其中,X是-CR21=N-;其中,R4至R8,R12,R13和R14是氢,和
R21是:
其中,v是0;r是0,Re是氢,u是0:
化合物 | R2 | R3 | Y | R49 |
189190191192193194 | ClClClHCH(CH3)2OCF3 | HHHClHH | SS(O)SSSS | CH3CH3CH2CH=CH2CH3CH3CH3 |
其中,X是-NR17-,Y是-CR24R25CR26R27-;其中,R1,R3至R7,R24至R25,是氢,v是0;u是0:
其中,X是-NR17;R1和R3至R8是氢:
化合物 | Y | R30 | R2 | R17 | R47 | R48 |
202 | S | ---- | H | C3H6NR47R48 | H | CH3 |
2032 | S | ---- | Cl | C3H6NR47R48 | H | CH(CH3)CH2Ph |
2046 | S | ---- | Cl | C3H6NR47R48 | CH3 | CH3 |
2054 | S | ---- | OCH3 | C3H6NR47R48 | CH3 | CH3 |
2062 | S | ---- | C(O)CH3 | C3H6NR47R48 | CH3 | CH3 |
2077 | S | ---- | CF3 | C3H6NR47R48 | -C2H4N(CH3)C2H4- | |
2087 | S | ---- | CF3 | C3H6NR47R48 | -C2H4N(C2H4OH)C2H4- | |
209 | O | ---- | H | C3H6NR47R48 | H | CH3 |
210 | O | ---- | H | C3H6NR47R48 | H | C3H7 |
211 | O | ---- | Cl | C3H6NR47R48 | H | CH3 |
212 | O | ---- | H | C3H6NR47R48 | CH3 | CH3 |
213 | NR30 | CH3 | H | C3H6NR47R48 | CH3 | CH3 |
214 | NR30 | C2H5 | H | C3H6NR47R48 | -C5H10- |
其中,X是-CR11R12CR13R14-;其中,R1,R3至R8,R13和R14是氢,v是0;m是0,Rb是氢,u是0:
1甲磺酸盐;2马来酸盐;3二甲磺酸盐;4二马来酸盐;5草酸盐;6盐酸盐;7二盐酸盐;8亚硫酸盐;9硫酸盐;10草酸盐-二配合物
测试对本发明有用的式I化合物的杀虫活性,方法是观察由试验化合物处理的棉花植物上棉蚜(Aphis gossypii)虫口死亡率,与未处理的植物上同样的棉蚜虫口相比。这些试验按照如下方式进行:
对于每个试验化合物的施用比率,选用二盆7至10天龄的大陆棉苗(Gossypium hirsutium),生长于7.6cm直径的花盆以供试验之用。每株试验植物寄生有约120只棉蚜成虫,这些棉蚜源自棉花植物上长大的棉蚜寄生处,放至每片试验植物剪下的叶上。感染后,试验植物最多保持约12小时,让棉蚜完全易位至试验植物上。将每个试验化合物10mg溶于1ml丙酮配成1000ppm溶液。每个溶液用9ml由0.03ml聚氧乙烯(10)异辛基苯醚在100ml水中的溶液进行稀释。每种试验化合物需约2.5ml喷洒至试验植物,每次试验均一式二份喷洒(对每个试验化合物总量为5ml)。如果需要,将上述1000ppm的试验化合物用10%丙酮和300ppm聚氧乙烯(10)异辛基苯基醚在水中的溶液作系列稀释,以提供较低施用比率配比之用,例如300ppm,100ppm,30ppm或10ppm。将试验化合物的溶液对每个试验植物一式二份喷洒,直至在叶子的上表面和下表面都喷到。对所有试验植物的喷洒均用Devilbus AtomizeR152型(SunriseMedical,Carsbad,CA)型器械,以约0.63-0.74kg/cm2的压力,对试验植物的距离约30.5cm进行。为作对照之用,配成标准溶液,诸如(amitraz)或(demethylchlordimeform(DCDM)),以类似上述方法配制,也用10%丙酮和聚氧乙烯(10)异辛基苯醚在水中的300ppm溶液但不含试验化合物,也同样喷洒在试验植物上。将试验化合物的溶液、标准溶液以及不含试验化合物的溶液喷完后,让植物晾干。干燥完全后,将试验植物放至含2.5cm高度水的浅盘中,置培养室中至少24小时。然后,评估每株植物由试验化合物引起的蚜虫虫口密度的减少,与不用试验化合物的蚜虫密度比较。如果用化合物在植物上喷洒后棉蚜的的死亡率为25-75%,则认为该化合物具有杀虫活性(SA)。如果试验植物上棉蚜死亡率为75%或更高,则认为该化合物有较高的杀虫活性(A)。如果棉蚜死亡率仅有20%或更低,则认为该试验化合物无活性(I)
所选的施用率的杀虫活性的结果列于表2。式I的试验化合物用与表1中相应的序号表示。
表2
一些三环衍生物的杀虫活性
化合物 | 棉蚜在棉花植物上的死亡率 | |
20-75%死亡率(SA) | 大于75%死亡率(A) | |
12378**91112131415162024263652 | XXXX | XXXXXXXXXXXXX |
化合物 | 棉蚜在棉花植物上的死亡率 | |
20-75%死亡率(SA) | 大于75%死亡率(A) | |
5354555657596061626364**65**66*67**6869*70*7172**73**74**75**7677**78**79**80**81**82**83**84**85**868788**89** | XXXXX | XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX |
化合物 | 棉蚜在棉花植物上的死亡率 | |
20-75%死亡率(SA) | 大于75%死亡率(A) | |
90919294**9596**97**98**99**100**101**102**103**104**105**106**107**108**109**110**111**112**113**114115**116117118**119**120121122**123**124**125**126** | XXXX | XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX |
化合物 | 棉蚜在棉花植物上的死亡率 | ||
20-75%死亡率(SA) | 大于75%死亡率(A) | ||
127**128**129131138**139**140**141142143144**145**146**147148149**150**151152**153**154**155**156157**158**159160**161**162163**164165166**167**168**169** | XXXXXX | XXXXXXXXXXXXXXXXXXXXXXXXXXXXX |
化合物 | 棉蚜在棉花植物上的死亡率 | |
20-75%死亡率(SA) | 大于75%死亡率(A) | |
170171**172173**178183**185**186**187**188189190191192193194203**204**205**206**2207**208**217 | XXX | XXXXXXXXXXXXXXXXXXXX |
施用比率1000ppm
*施用比率300ppm
**施用比率100ppm
如表2所示,几乎所有测试的式I化合物提供了75%或更高的棉蚜死亡率。
在按照和上面所述相同方式进行试验中,测试一些式I化合物,以确定棉蚜的更高的最后死亡率。表3列出所选施用率的杀虫活性数据和昆虫接触药剂时间。
表3
一些三环衍生物的杀虫活性
化合物 | 施用率(ppm) | 在棉花植物上的棉蚜死亡率 | 蚜虫接触测试化合物(小时) |
2389111215202652646566676970717273757677787980828385878889909294959697 | 100ppm100100100100100100100100300100100100100100100100100100100100100100100100010010010001000100100100010010001000300100 | 80%808826422628378410074100617569571001003586323753358398419297355574481008210065 | 96小时96967296729672727216816816816816816816816816816816816816816816816816816816816816816872727216872 |
化合物 | 施用率(ppm) | 在棉花植物上的棉蚜死亡率 | 蚜虫接触测试化合物(小时) |
9899100101102103104105106107108109110111112113115118119121122123124125126127128131138139140144145146149150151152153154 | 10010001000100100100010010001000100100010003001001001001001001001000100100100100100100010010010001001000100100300100100300300300100 | 9010082603390758510082100100659492789385856588969590100100959010096731009888689372749383 | 16816896727272168969616816816816872727272727272727272721681687216816816816816814472168727216816872 |
化合物 | 施用率(ppm) | 在棉花植物上的棉蚜死亡率 | 蚜虫接触测试化合物(小时) |
155156157158159160161162163166167168169171173183185186187189194205207208 | 100100100300100100100300100010030010010010010001000100010010010001005001000500 | 735564822871733196786677718582100100100945551402543 | 721681447272727216816814416872727296168168168168168168727272 |
如表3所示,这一试验中测试的式I化合物,60%的化合物表明大于或等于75%的棉蚜死亡率,而其余式I化合物,表明26-74%棉蚜对照。
虽然本发明的表述更着眼于优选实施方案的介绍,但本领域中的一般技术人员可理解,可以使用优选实施方案的各种变体,并且将本发明用于实践而不只在此详述。因此,本发明包括所有的变动均未离开如下列权利要求书所限定的实质和范围。
Claims (20)
1.一种杀虫剂组合物,包含杀虫剂有效量的至少一种式I的化合物和至少一种适于杀虫剂的载体,其中,式I的化合物为:
其中:
R1至R8独立地选自:氢、卤素、烷基、环烷基、链烯基、炔基、三烷基甲硅烷基炔基、烷氧基、卤烷基、卤烷氧基、烷硫基、烷基亚硫酰基、烷基磺酰基、卤烷硫基、卤烷基亚硫酰基、卤烷基磺酰基、二烷氨基磺酰基、硝基、氰基、氨基、甲酰基或烷基羰基;
X选自:-CR9R10-,-CR11R12CR13R14-,-CR15=CR16-,-NR17-,-CR18R19NR20-或-CR21=N-:
和
Y选自:-CR22R23-,-CR24R25CR26R27-,-CR28=CR29-,-NR30-,-CR31R32NR33-,-O-,-S-,-S(O)-,-S(O)2-,-CR34R35O-,-CR36R37S-,或-CR38=N-;
其中,
R9和R10独立地选自:氢、烷基或(哌啶-4-基)烷基;
其中,
R39,R40和R41独立地选自:氢、烷基、羟烷基、烷氧基烷基、烷硫基烷基、烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或,R40和R41与-C2H4N(CH3)C2H4-一起形成哌嗪环;
u是0或1,
而当u是1时,形成N-氧化物;
n是0,Ra是氢;
或,n是1-8,Ra选自:一个或多个烷基、烷氧基烷基、烷氧基羰基和芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R11选自:氢、烷基、烷氨基烷氧基、二烷氨基烷氧基、N(烷基)(烷氨基烷基)、N(烷基)(二烷氨基烷基)、烷氨基烷基炔基、二烷氨基烷基炔基、吗啉基、咪唑啉基、烷基吡咯烷氧基、
其中,
v是0或1,
当v是1,A是选自-O-,-S-,-NH-和-CH2-的桥基;
u按上面所述;
R42至R45独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基;烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或,R43和R44与-C5H10-一起形成一个哌啶环;
m,p和q是0,Rb,Rc和Rd是氢;
或,m是1-8,p是1-7和q是1-10,Rb,Rc和Rd分别独立地选自:一个或多个烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或,
R12,当不与R11一起时,R13,R14和R16独立地选自:氢、羟基、卤素、烷基、烷氧基、烷基羰基,烷基羰氧基,烷氧基羰基,烷氧基羰氧基,烷氨基羰基、二烷氨基羰基、烷氨基羰氧基、二烷氨基羰氧基、烷氨基磺酰基或二烷氨基磺酰基;
R15选自:
其中,m,u,v,A,Rb和R42按照上面所述;
R17是氢;烷基;烷氧基烷基;烷氧基羰基;二烷氨基烷基;烷氨基羰基;二烷氨基羰基;烷基磺酰基;芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或-C3H6NR47R48;
其中,
A,v和u按照上面所述;
R46选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R47和R48独立地选自:氢和烷基;
或
R47和R48可与-C5H10-一起形成一个哌啶环,或与-C2H4N(CH3)C2H4-或-C2H4N(C2H4OH)C2H4-一起形成哌嗪环;
R18和R19独立地选自:氢、烷基、氨基、烷氨基烷基和二烷氨基烷基;
R20选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基;
R21选自:氢、烷基、
其中,
A,v和u按照上面所述;
R49至R52独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基,烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基,杂芳烷基、杂芳基烷氨基,其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
或,R50和R51与-C5H10-一起形成一个哌啶环;
r,s和t是0,Re,Rf和Rg是氢,
或,r是1-8,s是1-7,t是1-10,Re,Rf和Rg分别独立地选自:一个或多个烷基、烷氧基烷基、烷氨基、二烷氨基、烷氧基羰基或芳基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R22至R29独立地选自:氢和烷基;
R30选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基;芳基和芳烷基其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R31和R32独立地选自:氢和烷基;
R33选自:氢、烷基、烷氧基烷基、烷氧基羰基、二烷氨基烷基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、芳基和芳烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R34至R38独立地选自:氢和烷基;
及其农业上可接受的盐。
2.如权利要求1所述的杀虫剂组合物,其特征在于,X是-CR9R10-,Y选自:-O-,-S-,-CR22R23-和-CR34R35O-;
其中,
R9和R10与
一起;
其中,
R39选自:氢、烷基、羟烷基、烷氧基烷基、烷硫基烷基、烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基,其中芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
而R22,R23,R34和R35独立地选自:氢和烷基。
3.如权利要求1所述的杀虫剂组合物,其特征在于X是-CR11R12CR13R14-,Y选自:-O-,-S-和-CR22R23-;
其中,
R11选自:
和
其中,
R42和R45独立地选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基烷基、卤烷氧基羰基、芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基、杂芳烷基、杂芳基烷氨基;其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
R12选自:氢、羟基、卤素、烷基、烷氧基、烷基羰基、烷基羰氧基、烷氧基羰基、烷氧基羰氧基、烷氨基羰基、二烷氨基羰基、烷氨基羰氧基、二烷氨基羰氧基、烷氨基磺酰基和二烷氨基磺酰基;
R13和R14是氢;
R22和R23独立地选自:氢和烷基。
4.如权利要求1所述的杀虫剂组合物,其特征在于,X是-CR18R19NR20-,Y选自:-O-,-S-和-CR22R23-;
其中,
R20选自:氢、烷基、烷氧基烷基、烷氧基羰基,二烷氨基烷基、烷氨基羰基和二烷氨基羰基;
而,R22和R23独立地选自:氢和烷基。
5.如权利要求1所述的杀虫剂组合物,其特征在于,X是-CR21=N-,Y选自:-S-和-CR22R23-;
其中,R21是
其中,
R49选自:氢、烷基、链烯基、炔基、羟烷基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基烷基、卤烷氧基羰基;芳烷基、芳氧基烷基、芳基羰基烷基、芳基羰氧基烷基、杂芳基,杂芳烷基、杂芳基烷氨基,其中芳基和杂芳基任选被一个或多个卤素、烷氧基、卤烷基或芳基取代;
而R22和R23独立地选自:氢和烷基。
6.如权利要求1所述的杀虫剂组合物,还包含一种或多种第二化合物。
7.如权利要求2所述的杀虫剂组合物,还包含一种或多种第二化合物。
8.如权利要求3所述的杀虫剂组合物,还包含一种或多种第二化合物。
9.如权利要求4所述的杀虫剂组合物,还包含一种或多种第二化合物。
10.如权利要求5所述的杀虫剂组合物,还包含一种或多种第二化合物。
11.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求1所述的组合物。
12.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求2所述的组合物。
13.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求3所述的组合物。
14.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求4所述的组合物。
15.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求5所述的组合物。
16.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求6所述的组合物。
17.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求7所述的组合物。
18.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求8所述的组合物。
19.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求9所述的组合物。
20.一种防治昆虫的方法,在存在昆虫或预期会出没的所在地域施用杀虫剂有效量的权利要求10所述的组合物。
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US60/411,926 | 2002-09-18 |
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US (1) | US20060111342A1 (zh) |
EP (1) | EP1538906A2 (zh) |
JP (1) | JP2005539076A (zh) |
KR (1) | KR20050048633A (zh) |
CN (1) | CN1681388A (zh) |
AR (1) | AR041197A1 (zh) |
AU (1) | AU2003272362A1 (zh) |
BR (1) | BR0314108A (zh) |
MX (1) | MXPA05002884A (zh) |
TW (1) | TW200418383A (zh) |
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CN105884758A (zh) * | 2015-02-13 | 2016-08-24 | 广东东阳光药业有限公司 | 三环化合物及其在药物中的应用 |
CN110128432A (zh) * | 2018-02-02 | 2019-08-16 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
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WO2003039255A1 (en) * | 2001-11-05 | 2003-05-15 | Basf Aktiengesellschaft | Use of substituted dibenzothiepine derivatives as insecticidal, acaricidal and nematicidal agents |
BRPI0406592A (pt) * | 2003-01-23 | 2005-12-20 | Acadia Pharm Inc | Usos de n-desmetilclozapina, métodos para o tratamento de psicose, de distúrbios afetivos, de demência, de dor neuropática e de glaucoma e composição farmacêutica |
US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
JP4810423B2 (ja) | 2003-06-27 | 2011-11-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 三環式デルタオピオイド調節剤 |
PT1696931E (pt) * | 2003-12-22 | 2009-06-12 | Acadia Pharm Inc | Análogos diaril[a,d]ciclo-hepteno substituídos com amino utilizados como agonistas muscarínicos e métodos de tratamento de perturbações neuropsiquiátricas |
BRPI0509524A (pt) * | 2004-04-01 | 2007-09-18 | Acadia Pharm Inc | formas cristalinas de n-desmetilclozapina |
WO2007030089A1 (en) | 2004-08-05 | 2007-03-15 | Janssen Pharmaceutica N.V. | Tricyclic delta- opioid modulators |
BRPI0519201A2 (pt) | 2004-12-22 | 2008-12-30 | Janssen Pharmaceutica Nv | moduladores de delta-opiàide tricÍclico |
WO2006069276A2 (en) | 2004-12-22 | 2006-06-29 | Janssen Pharmaceutica N.V. | TRICYCLIC ō-OPIOID MODULATORS |
JP2008526878A (ja) | 2005-01-06 | 2008-07-24 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 三環式δ−オピオイド調節剤 |
DE602006018604D1 (de) * | 2005-06-16 | 2011-01-13 | Janssen Pharmaceutica Nv | Tricyclische opioidmodulatoren |
WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
US8461145B2 (en) | 2007-12-05 | 2013-06-11 | Janssen Pharmaceutica Nv | Dibenzoazepine and dibenzooxazepine TRPA1 agonists |
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CN109897027B (zh) * | 2019-04-28 | 2021-11-02 | 梯尔希(南京)药物研发有限公司 | 一种3-羟基地氯雷他定代谢物的合成方法 |
CN114929688A (zh) | 2019-10-21 | 2022-08-19 | 阿莱瑞恩公司 | 作为H1和5-HT2A-受体调节剂、用于治疗睡眠障碍的3-(4-(11H-二苯并[b,e][1,4]吖庚英-6-基)哌嗪-1-基)-和3-(4-(二苯并[b,f][1,4]氧杂吖庚英/硫杂吖庚英/二吖庚英-11-基)哌嗪-1-基)-丙酸衍生物 |
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- 2003-09-12 WO PCT/US2003/028791 patent/WO2004026030A2/en active Application Filing
- 2003-09-12 US US10/528,740 patent/US20060111342A1/en not_active Abandoned
- 2003-09-12 CN CNA038221136A patent/CN1681388A/zh active Pending
- 2003-09-12 EP EP03754541A patent/EP1538906A2/en not_active Withdrawn
- 2003-09-12 KR KR1020057004378A patent/KR20050048633A/ko not_active Application Discontinuation
- 2003-09-15 TW TW092125356A patent/TW200418383A/zh unknown
- 2003-09-16 AR ARP030103353A patent/AR041197A1/es not_active Application Discontinuation
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Cited By (5)
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CN105884758A (zh) * | 2015-02-13 | 2016-08-24 | 广东东阳光药业有限公司 | 三环化合物及其在药物中的应用 |
CN105884758B (zh) * | 2015-02-13 | 2019-12-10 | 广东东阳光药业有限公司 | 三环化合物及其在药物中的应用 |
TWI698430B (zh) * | 2015-02-13 | 2020-07-11 | 南北兄弟藥業投資有限公司 | 三環化合物及其在藥物中的應用 |
CN110128432A (zh) * | 2018-02-02 | 2019-08-16 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
CN110128432B (zh) * | 2018-02-02 | 2021-03-02 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
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AU2003272362A1 (en) | 2004-04-08 |
KR20050048633A (ko) | 2005-05-24 |
US20060111342A1 (en) | 2006-05-25 |
EP1538906A2 (en) | 2005-06-15 |
WO2004026030A3 (en) | 2004-06-03 |
ZA200501774B (en) | 2005-11-30 |
MXPA05002884A (es) | 2005-06-22 |
BR0314108A (pt) | 2006-04-25 |
AR041197A1 (es) | 2005-05-04 |
WO2004026030A2 (en) | 2004-04-01 |
JP2005539076A (ja) | 2005-12-22 |
TW200418383A (en) | 2004-10-01 |
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