[go: up one dir, main page]

CN1261884A - Benzothiophene derivatives used as herbicides - Google Patents

Benzothiophene derivatives used as herbicides Download PDF

Info

Publication number
CN1261884A
CN1261884A CN 98806742 CN98806742A CN1261884A CN 1261884 A CN1261884 A CN 1261884A CN 98806742 CN98806742 CN 98806742 CN 98806742 A CN98806742 A CN 98806742A CN 1261884 A CN1261884 A CN 1261884A
Authority
CN
China
Prior art keywords
alkyl
alkoxy
haloalkyl
alkenyl
alkynyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN 98806742
Other languages
Chinese (zh)
Inventor
H·雷普弗勒
A·埃德蒙兹
A·德梅斯迈克
K·塞金杰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Novartis AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novartis AG filed Critical Novartis AG
Publication of CN1261884A publication Critical patent/CN1261884A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • A01N43/12—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 condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A compound of the general formula (I) wherein R1Is C1－C4Alkyl radical, C1－C4Haloalkyl, C1－C4alkoxy-C1－C4Alkyl radical, C1－C4Alkoxycarbonyl, cyano C1－C4Alkyl, hydroxy-C1－C4Alkyl, amino-C1－C4Alkyl, CHO, C1－C4alkyl-ON = CH, C2－C6Alkenyl radical, C1－C4alkoxycarbonyl-C2－C6Alkenyl OR the radical-CH 20)OR21;R20And R21Independently of one another are C1－C4Alkyl, or R20And R21Together are- (CH)2)nl－;n1Is 2,3 or 4, R2Is hydrogen or C1－C4Alkyl radical R3And R4Independently of one another are hydrogen, C1－C4Alkyl or halogen, n is 0,1 or 2, R5Is C1－C4Alkyl radical, C1－C4Haloalkyl, C2－C6Alkenyl radical, C2－C6Alkynyl, C1－C4Alkoxy radical, C1－C4Halogenoalkoxy, C1－C4alkyl-S (O)n2,(C1－C4Alkyl radical)2NS(O)2,C1－C4alkyl-S (O)2O, halogen, nitro or cyano, n2Is 0,1 or 2, Q is OH, halogen or radical (Q)1)、(Q2)、(Q3)、(Q4)、(Q5) Or (Q)6) And R6－R14W, Y and n6As defined in claim 1, and the agrochemically acceptable salts and stereoisomers of the compounds of formula have good pre-and post-emergent selective herbicidal properties. Processes for the preparation of these compounds and their use as herbicidal active ingredients are described.

Description

用作除草剂的苯并噻吩衍生物Benzothiophene derivatives used as herbicides

本发明涉及新型的除草活性的取代双环苯甲酰基衍生物，涉及其制备方法，涉及包括这些化合物的组合物，和涉及它们在控制杂草，尤其控制在有用植物的作物例如禾谷米，玉米，稻谷，棉花，大豆，油菜，高梁，甘蔗，糖用甜菜，向日葵，蔬菜，种植作物和饲料植物中的杂草的用途，或在抑制植物生长上的用途。The present invention relates to novel herbicidally active substituted bicyclic benzoyl derivatives, to processes for their preparation, to compositions comprising these compounds, and to their use in controlling weeds, especially crops of useful plants such as cereals, maize , rice, cotton, soybean, rapeseed, sorghum, sugar cane, sugar beet, sunflower, vegetables, the use of weeds in planting crops and forage plants, or the use in inhibiting the growth of plants.

具有除草活性的异噁唑基-和吡唑基-苯甲酰基和双环苯甲酰基衍生物是已知的和描述在例如WO 96/26192，WO 96/26206和WO 97/08164中。Herbicidally active isoxazolyl- and pyrazolyl-benzoyl and bicyclic benzoyl derivatives are known and described, for example, in WO 96/26192, WO 96/26206 and WO 97/08164.

现已发现新的具有除草和生长抑制性能的取代双环苯甲酰基衍生物。Novel substituted bicyclic benzoyl derivatives having herbicidal and growth inhibitory properties have now been discovered.

所以本发明涉及通式I的化合物；

Figure A9880674200101
其中R1是C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基-C1-C4烷基，C1-C4烷氧基羰基，氰基，氰基C1-C4烷基，羟基-C1-C4烷基，氨基-C1-C4烷基，CHO，C1-C4烷基-ON＝CH，C2-C6链烯基，C1-C4烷氧基羰基-C2-C6链烯基或基团-CH(OR20)OR21；The present invention therefore relates to compounds of general formula I;
Figure A9880674200101
wherein R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy- C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl, cyano, Cyano C 1 -C 4 alkyl, hydroxy-C 1 -C 4 alkyl, amino - C 1 -C 4 alkyl, CHO, C 1 -C 4 alkyl-ON=CH, C 2 -C 6 chain Alkenyl, C 1 -C 4 alkoxycarbonyl-C 2 -C 6 alkenyl or group -CH(OR 20 )OR 21 ;

R20和R21相互独立地是C1-C4烷基；或R20和R21一起是-(CH2)n1-；n1是2，3或4；R2是氢或C1-C4烷基；R3和R4相互独立地是氢，C1-C4烷基或卤素；n是0，1或2；R5是C1-C4烷基，C1-C4卤代烷基，C2-C6链烯基，C2-C6炔基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基-S(O)n2，(C1-C4烷基)2NS(O)2，C1-C4烷基-S(O)2O，卤素，硝基或氰基；n2是0，1或2；Q是OH，卤素或基团

Figure A9880674200111
Figure A9880674200112
R6和R7相互独立地是氢，OH，C1-C4烷基，C2-C6链烯基，C2-C6炔基，C1-C4烷氧基羰基，C1-C4烷基-S(O)n2，C1-C4烷基-NHS(O)2，苯基或被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，氨基，C1-C4烷基氨基，二-C1-C4烷基氨基，C1-C4烷基-S(O)n2，C1-C4烷基-S(O)2O，C1-C4卤代烷基-S(O)n2，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代的苯基；或R6和R7相互独立地是C1-C4卤代烷基，-NH-C1-C4烷基，-N(C1-C4烷基)2，C1-C6烷氧基，氰基，硝基或卤素；或相邻R6和R7一起是-(CH2)n3-；n3是2，3，4，5或6；W是氧，硫，-C(R18)2-或-N(R22)-；n6是0或1，或当W是-C(R18)2-时，n6另外可以是2或3；各R18独立地是氢，C1-C4烷基，C1-C4卤代烷基或C1-C4烷氧基羰基；或当n6是1时，R18与相邻取代基R7中的一个形成单键，和剩下的成对的R6和R7是氢以外的基团；R22是氢，C1-C4烷基或C1-C4烷氧基羰基；R8是OH，C1-C4烷氧基，C1-C4烷基羰基氧基，C1-C4烷氧基羰基氧基，R23R24N-C(O)O，苯硫基，C1-C4烷硫基，C1-C4烷基-S(O)2O，(C1-C4烷氧基)2P(O)O，C1-C4烷基(C1-C4烷氧基)P(O)O，H(C1-C4烷氧基)P(O)O或苯甲酰氧基；R23和R24相互独立地是氢或C1-C4烷基；Y是氧，硫或-(CH2)n5-；n5是0，1，2，3或4；R9是氢，C1-C6烷基，C1-C4烷基羰基，C1-C4烷氧基羰基，(C1-C4烷基)NHCO或(C1-C4烷基)2NCO；R10，R11和R12各自独立地是氢，C1-C4烷基，C1-C4烷氧基羰基，苯基或被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，氨基，C1-C4烷基氨基，二-C1-C4烷基氨基，C1-C4烷基-S(O)n2，C1-C4烷基-S(O)2O，C1-C4卤代烷基-S(O)n2，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代的苯基；R13是氢；卤素；C1-C4烷基；被未取代或R17取代的苯基所取代的C1-C4烷基；C1-C4卤代烷基；C2-C6链烯基；被未取代或R17-取代的苯基所取代的C2-C6链烯基；C2-C6炔基；被来取代或R17取代的苯基所取代的C2-C6炔基；C3-C6卤代链烯基；C3-C6卤代炔基；C3-C6环烷基；被卤素，R15或COOR16取代的C3-C6环烷基；COOR16；COR15；氰基；硝基；CONH2；(C1-C4烷基)NHCO；(C1-C4烷基)2NCO；(C1-C4卤代烷基)NHCO；(C1-C4卤代烷基)2NCO；C1-C4烷基S(O)n2；被未取代或R17-取代的苯基所取代的C1-C4烷基-S(O)n2；C1-C4烷氧基-C2-C6烷基-S(O)n2；C2-C6链烯基-S(O)n2；被未取代或R17-取代的苯基所取代的C2-C6链烯基-S(O)n2；C2-C6炔基-S(O)n2；或被未取代或R17-取代的苯基所取代的C2-C6炔基-S(O)n2；R15是C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基，苯基或R17-取代的苯基；R16是氢，C1-C4烷基或C1-C4卤代烷基；R17是卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基，C1-C4烷氧基-C1-C4烷基，C1-C4烷氧基-C3-C6链烯基，C1-C4烷氧基-C3-C6炔基，氰基，硝基，COOH，C1-C4烷氧基羰基，C1-C4卤代烷氧基羰基，C1-C4烷基S(O)n2，C1-C4卤代烷基-S(O)n2，苯基-S(O)n2；在苯环上被卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6炔基，氰基，硝基，COOH，C1-C4烷氧基羰基，C1-C4烷基-S(O)n2，C1-C4卤代烷基-S(O)n2，C1-C4烷基羰基，二-C1-C4烷基氨基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基-S(O)2O或C1-C4卤代烷基-S(O)2O取代的苯基-S(O)n2；C1-C4烷基羰基，二-C1-C4烷基氨基，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，C1-C4卤代烷基-S(O)2NH，C1-C4卤代烷基-S(O)2N(C1-C4烷基)，NH2S(O)2，(C1-C4烷基)NHS(O)2，(C1-C4烷基)2NS(O)2，CONH2，(C1-C4烷基)NHCO，(C1-C4烷基)2NCO，NH2CS，(C1-C4烷基)NHCS，(C1-C4烷基)2NCS，C1-C4烷氧基，C1-C4卤代烷氧基，C3-C6链烯基氧基，C3-C6炔基氧基，C1-C4烷基-S(O)2O，C1-C4卤代烷基-S(O)2O，苯基-S(O)2O或在苯环上被卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6炔基，氰基，硝基，COOH，C1-C4烷氧基羰基，C1-C4烷基-S(O)n2，C1-C4卤代烷基S(O)n2，C1-C4烷基羰基，二-C1-C4烷基氨基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基S(O)2O或C1-C4卤代烷基-S(O)2O取代的苯基S(O)2O；和R14是C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基，C3-C6环烷基或被以下基团取代的C3-C6环烷基：卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基，苯基或被卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6炔基，氰基，硝基，COOH，C1-C4烷氧基羰基，C1-C4烷基-S(O)n2，C1-C4卤代烷基-S(O)n2，C1-C4烷基羰基，二-C1-C4烷基氨基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基-S(O)2O或C1-C4卤代烷基S(O)2O取代的苯基，及通式I化合物的农业化学上可接受的盐类和其立体异构体。R 20 and R 21 are independently C 1 -C 4 alkyl; or R 20 and R 21 together are -(CH 2 ) n1 -; n 1 is 2, 3 or 4; R 2 is hydrogen or C 1 - C 4 alkyl; R 3 and R 4 are independently hydrogen, C 1 -C 4 alkyl or halogen; n is 0, 1 or 2; R 5 is C 1 -C 4 alkyl, C 1 -C 4 Haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl-S(O) n2 , (C 1 -C 4 alkyl) 2 NS(O) 2 , C 1 -C 4 alkyl-S(O) 2 O, halogen, nitro or cyano; n 2 is 0, 1 or 2; Q is OH, halogen or radical
Figure A9880674200111
Figure A9880674200112
R 6 and R 7 are independently hydrogen, OH, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl-S(O) n2 , C 1 -C 4 alkyl-NHS(O) 2 , phenyl or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, amino, C 1 -C 4 alkylamino, di-C 1 -C 4 Alkylamino, C 1 -C 4 Alkyl-S(O) n2 , C 1 -C 4 Alkyl-S(O) 2 O, C 1 -C 4 Haloalkyl-S(O) n2 , C 1 -C 4 haloalkyl-S(O) 2 O, C 1 -C 4 alkyl-S(O) 2 NH, C 1 -C 4 alkyl-S(O) 2 N(C 1 -C 4 alkyl ), halogen, nitro, COOH or cyano-substituted phenyl; or R 6 and R 7 are independently C 1 -C 4 haloalkyl, -NH-C 1 -C 4 alkyl, -N(C 1 -C 4 alkyl) 2 , C 1 -C 6 alkoxy, cyano, nitro or halogen; or adjacent R 6 and R 7 together are -(CH 2 ) n3 -; n 3 is 2,3, 4, 5 or 6; W is oxygen, sulfur, -C(R 18 ) 2 - or -N(R 22 )-; n 6 is 0 or 1, or when W is -C(R 18 ) 2 -, n6 can additionally be 2 or 3; each R18 is independently hydrogen, C1 - C4 alkyl, C1 - C4 haloalkyl or C1 - C4 alkoxycarbonyl; or when n6 is 1 , R 18 forms a single bond with one of the adjacent substituents R 7 , and the remaining pair of R 6 and R 7 is a group other than hydrogen; R 22 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl; R 8 is OH, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyloxy, C 1 -C 4 alkoxycarbonyloxy, R 23 R 24 NC(O)O, phenylthio, C 1 -C 4 alkylthio, C 1 -C 4 alkyl-S(O) 2 O, (C 1 -C 4 alkoxy) 2 P(O)O , C 1 -C 4 alkyl(C 1 -C 4 alkoxy)P(O)O, H(C 1 -C 4 alkoxy)P(O)O or benzoyloxy; R 23 and R 24 are independently hydrogen or C 1 -C 4 alkyl; Y is oxygen, sulfur or -(CH 2 ) n5 -; n 5 is 0, 1, 2, 3 or 4; R 9 is hydrogen, C 1 -C 6 alkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, (C 1 -C 4 alkyl) NHCO or (C 1 -C 4 alkyl) 2 NCO; R 10 , R 11 and R 12 are each independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl, phenyl or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, amino, C 1 -C 4 alkylamino, di- C 1 -C 4 alkylamino, C 1 -C 4 alkyl-S(O) n2 , C 1 -C 4 alkyl-S(O) 2 O, C 1 -C 4 haloalkyl-S(O) n2 , C 1 -C 4 haloalkyl-S(O) 2 O, C 1 -C 4 alkyl-S(O) 2 NH, C 1 -C 4 alkyl-S(O) 2 N(C 1 - C 4 alkyl), halogen, nitro, COOH or cyano substituted phenyl; R 13 is hydrogen; halogen; C 1 -C 4 alkyl; C 1 substituted by unsubstituted or R 17 substituted phenyl -C 4 alkyl; C 1 -C 4 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 alkenyl substituted by unsubstituted or R 17 -substituted phenyl; C 2 -C 6 alkynyl; C 2 -C 6 alkynyl substituted by substituted or R 17 substituted phenyl; C 3 -C 6 haloalkenyl; C 3 -C 6 haloalkynyl; C 3 -C 6 cycloalkyl; C 3 -C 6 cycloalkyl substituted by halogen, R 15 or COOR 16 ; COOR 16 ; COR 15 ; cyano; nitro; CONH 2 ; (C 1 -C 4 alkyl)NHCO; (C 1 -C 4 alkyl) 2 NCO; (C 1 -C 4 haloalkyl) NHCO; (C 1 -C 4 haloalkyl) 2 NCO; C 1 -C 4 alkyl S(O) n2 ; C 1 -C 4 alkyl-S(O) n2 substituted or R 17 -substituted phenyl; C 1 -C 4 alkoxy-C 2 -C 6 alkyl-S(O) n2 ; C 2 -C 6 alkenyl-S(O) n2 ; C 2 -C 6 alkenyl-S(O) n2 substituted by unsubstituted or R 17 -substituted phenyl; C 2 -C 6 alkynyl -S(O) n2 ; or C 2 -C 6 alkynyl-S(O) n2 substituted by unsubstituted or R 17 -substituted phenyl; R 15 is C 1 -C 4 alkyl, C 1 - C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, phenyl or R 17 -substituted phenyl; R 16 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 17 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl , C 1 -C 4 alkoxy-C 3 -C 6 alkenyl, C 1 -C 4 alkoxy-C 3 -C 6 alkynyl, cyano, nitro, COOH, C 1 -C 4 alkane Oxycarbonyl, C 1 -C 4 haloalkoxycarbonyl, C 1 -C 4 alkyl S(O) n2 , C 1 -C 4 haloalkyl-S(O) n2 , phenyl-S(O) n2 ; Halogenated on the benzene ring, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyano, nitro, COOH, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl-S(O) n2 , C 1 -C 4 haloalkyl-S(O) n2 , C 1 -C 4 alkylcarbonyl, di-C 1 - C 4 alkylamino, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl-S(O) 2 O or C 1 -C 4 haloalkyl-S(O ) 2 O-substituted phenyl-S(O) n2 ; C 1 -C 4 alkylcarbonyl, di-C 1 -C 4 alkylamino, C 1 -C 4 alkyl-S(O) 2 NH, C 1 -C 4 alkyl-S(O) 2 N(C 1 -C 4 alkyl), C 1 -C 4 haloalkyl-S(O) 2 NH, C 1 -C 4 haloalkyl-S(O) 2 N(C 1 -C 4 alkyl), NH 2 S(O) 2 , (C 1 -C 4 alkyl)NHS(O) 2 , (C 1 -C 4 alkyl) 2 NS(O) 2 , CONH 2 , (C 1 -C 4 alkyl) NHCO, (C 1 -C 4 alkyl) 2 NCO, NH 2 CS, (C 1 -C 4 alkyl) NHCS, (C 1 -C 4 alkyl) ) 2 NCS, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 4 alkyl -S(O) 2 O, C 1 -C 4 haloalkyl-S(O) 2 O, phenyl-S(O) 2 O or halogenated on the benzene ring, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyano, nitro, COOH, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl-S (O) n2 , C 1 -C 4 haloalkyl S(O) n2 , C 1 -C 4 alkylcarbonyl, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, C 1 - C 4 haloalkoxy, C 1 -C 4 alkylS(O) 2 O or C 1 -C 4 haloalkyl-S(O) 2 O substituted phenyl S(O) 2 O; and R 14 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 halo Alkynyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by: halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 Alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, phenyl or halogenated, C 1 -C 4 alkyl, C 1 - C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyano, nitro, COOH, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl-S( O) n2 , C 1 -C 4 haloalkyl-S(O) n2 , C 1 -C 4 alkylcarbonyl, di-C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, C 1 - C 4 haloalkoxy, C 1 -C 4 alkyl-S(O) 2 O or C 1 -C 4 haloalkyl S(O) 2 O substituted phenyl, and the agrochemically acceptable compound of general formula I salts and their stereoisomers.

在以上定义中，卤素被理解为碘或优选氟，氯或溴。In the above definitions, halogen is understood as iodine or preferably fluorine, chlorine or bromine.

取代基定义中的烷基，链烯基和炔基可以是直链或支链的，这同样适用于下面基团的烷基，链烯基和炔基部分：烷基羰基，氰基烷基，烷氧基烷基，烷硫基，烷基磺酰基，烷基氨基羰基，二烷基氨基羰基，(烷基)2NS(O)2，烷基(烷氧基)P(O)O，被未取代或R17-取代的苯基所取代的烷基，被未取代或R17-取代的苯基所取代的链烯基，烷氧基羰基链烯基，烷基S(O)2N(烷基)，(烷基)2NCO，(烷基)2NCS，被未取代或R17-取代的苯基所取代的链烯基-S(O)n2，烷氧基链烯基，链烯基氧基和炔基氧基。The alkyl, alkenyl and alkynyl groups in the substituent definitions may be straight-chain or branched, the same applies to the alkyl, alkenyl and alkynyl moieties of the following groups: alkylcarbonyl, cyanoalkyl , Alkoxyalkyl, Alkylthio, Alkylsulfonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, (Alkyl) 2 NS(O) 2 , Alkyl(Alkoxy)P(O)O , alkyl substituted by unsubstituted or R 17 -substituted phenyl, alkenyl substituted by unsubstituted or R 17 -substituted phenyl, alkoxycarbonyl alkenyl, alkyl S(O) 2 N(alkyl), (alkyl) 2 NCO, (alkyl) 2 NCS, alkenyl substituted by unsubstituted or R 17 -substituted phenyl-S(O) n2 , alkoxyalkene radical, alkenyloxy and alkynyloxy.

烷基是，例如，甲基，乙基，正丙基，异丙基，正丁基，仲丁基，异丁基，叔丁基以及戊基和己基的各种异构体。甲基，乙基，正丙基，异丙基和正丁基是优选的。Alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and the various isomers of pentyl and hexyl. Methyl, ethyl, n-propyl, isopropyl and n-butyl are preferred.

可提及的链烯基例子是乙烯基，烯丙基，甲代烯丙基，1-甲基乙烯基，丁-2-烯-1-基，戊烯基和2-己烯基，更优选链长为3-5个碳原子的链烯基。Examples of alkenyl groups that may be mentioned are vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl and 2-hexenyl, more Alkenyl groups having a chain length of 3 to 5 carbon atoms are preferred.

可提及的炔基实例是乙炔基，炔丙基，1-甲基炔丙基，3-丁炔基，丁-2-炔-1-基，2-甲基丁-3-炔-2-基，丁-3-炔-2-基，1-戊炔基，戊-4-炔-1-基和2-己炔基，优选链长为2-4个碳原子的炔基。Examples of alkynyl groups that may be mentioned are ethynyl, propargyl, 1-methylpropargyl, 3-butynyl, but-2-yn-1-yl, 2-methylbut-3-yn-2 -yl, but-3-yn-2-yl, 1-pentynyl, pent-4-yn-1-yl and 2-hexynyl, preferably alkynyl with a chain length of 2 to 4 carbon atoms.

合适的卤代烷基是被卤素单或多取代的，尤其单-至三-取代的烷基，卤素尤其是碘或特别为氟，氯或溴，例如氟甲基，二氟甲基，三氟甲基，氯甲基，二氯甲基，三氯甲基，2-氟乙基，2，2-二氟乙基，2-氯乙基，2，2-二氯乙基，2，2，2-三氟乙基和2，2，2-三氯乙基。Suitable haloalkyl groups are mono- or polysubstituted, especially mono- to tri-substituted alkyl groups, by halogen, especially iodine or especially fluorine, chlorine or bromine, e.g. fluoromethyl, difluoromethyl, trifluoromethyl Base, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2, 2-trifluoroethyl and 2,2,2-trichloroethyl.

合适的卤代链烯基是被卤素单-或多-取代的链烯基，卤素尤其是溴，碘或特别为氟或氯，例如2或3-氟丙烯基，2-或3-氯丙烯基，2-或3-溴丙烯基，2，3，3-三氟丙烯基，2，3，3-三氯丙烯基，4，4，4-三氟丁-2-烯-1-基和4，4，4-三氯丁-2-烯-1-基。被卤素单-、二-或三-取代的链烯基中，优选链长为3或4个碳原子的那些。链烯基可被卤素在饱和或不饱和碳原子上取代。Suitable haloalkenyl groups are alkenyl groups which are mono- or poly-substituted by halogen, especially bromine, iodine or especially fluorine or chlorine, for example 2- or 3-fluoropropenyl, 2- or 3-chloropropenyl Base, 2- or 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluorobut-2-en-1-yl and 4,4,4-trichlorobut-2-en-1-yl. Of the alkenyl groups mono-, di- or tri-substituted by halogen, those having a chain length of 3 or 4 carbon atoms are preferred. Alkenyl groups may be substituted by halogen on saturated or unsaturated carbon atoms.

合适的卤代炔基是，例如，被卤素单或多取代的炔基，卤素是溴，碘或特别为氟或氯，例如3-氟丙炔基，3-氯丙炔基，3-溴丙炔基，3，3，3-三氟丙炔基和4，4，4-三氟-丁-2-炔-1-基。Suitable haloalkynyl groups are, for example, mono- or polysubstituted alkynyl groups by halogen, which is bromine, iodine or especially fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl propynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluoro-but-2-yn-1-yl.

烷基磺酰基是，例如，甲基磺酰基，乙基磺酰基，丙基磺酰基，异丙基磺酰基，正丁基磺酰基，异丁基磺酰基，仲丁基磺酰基，叔丁基磺酰基或戊基-磺酰基或己基磺酰基的异构体；优选甲基磺酰基或乙基磺酰基。Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butyl Sulfonyl or isomers of pentyl-sulfonyl or hexylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.

卤代烷基磺酰基是，例如，氟甲基磺酰基，二氟甲基磺酰基，三氟甲基磺酰基，氯甲基磺酰基，三氯甲基磺酰基，2-氟乙基磺酰基，2，2，2-三氟乙基磺酰基或2，2，2-三氯乙基磺酰基。Haloalkylsulfonyl is, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2- , 2,2-trifluoroethylsulfonyl or 2,2,2-trichloroethylsulfonyl.

链烯基磺酰基是，例如，烯丙基磺酰基，甲代烯丙基磺酰基，丁-2-烯-1-基磺酰基，戊烯基磺酰基或2-己烯基磺酰基。Alkenylsulfonyl is, for example, allylsulfonyl, methallylsulfonyl, but-2-en-1-ylsulfonyl, pentenylsulfonyl or 2-hexenylsulfonyl.

氰基烷基是，例如，氰基甲基，氰基乙基，氰基乙-1-基或氰基正丙基。Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl or cyano-n-propyl.

烷基氨基是，例如，甲基氨基，乙基氨基或丙基-或丁基-氨基的异构体。Alkylamino is, for example, methylamino, ethylamino or the isomers of propyl- or butyl-amino.

二烷基氨基是，例如，二甲基氨基，二乙基氨基或二丙基-或二丁基-氨基的异构体。Dialkylamino is, for example, dimethylamino, diethylamino or the isomers of dipropyl- or dibutyl-amino.

烷基羰基尤其是乙酰基或丙酰基。Alkylcarbonyl is especially acetyl or propionyl.

烷氧基是，例如，甲氧基，乙氧基，正丙氧基，异丙氧基，正丁氧基，异丁氧基，仲丁氧基或叔丁氧基。Alkoxy is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy.

链烯基氧基是，例如，烯丙氧基，甲代烯丙氧基或丁-2-烯-1-基氧基。Alkenyloxy is, for example, allyloxy, methallyloxy or but-2-en-1-yloxy.

炔氧基是，例如，炔丙氧基或1-甲基炔丙氧基。Alkynyloxy is, for example, propargyloxy or 1-methylpropargyloxy.

烷氧基烷基是，例如，甲氧基甲基，甲氧基乙基，乙氧基甲基，乙氧基乙基，正丙氧基甲基，正丙氧基乙基，异丙氧基甲基或异丙氧基乙基。Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy oxymethyl or isopropoxyethyl.

烷氧基羰基是，例如，甲氧基羰基，乙氧基羰基，正丙氧基羰基，异丙氧基羰基或正丁氧基羰基，优选甲氧基羰基或乙氧基羰基。Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl or n-butoxycarbonyl, preferably methoxycarbonyl or ethoxycarbonyl.

卤代烷氧基是，例如，氟甲氧基，二氟甲氧基，三氟甲氧基，2，2，2-三氟乙氧基，1，1，2，2-四氟乙氧基，2-氟乙氧基，2-氯乙氧基，2，2，2-三氯乙氧基或五氟乙氧基。Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy.

适合作为取代基的环烷基是，例如，环丙基，环丁基，环戊基和环己基。Suitable cycloalkyl groups as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

适合作取代基的卤代环烷基是，例如，单-，二-或全-卤代环烷基，例如氟环丙基，氯环丙基，溴环丙基，2，2-二氯环丙基，2，2-二氟环丙基，2，2-二溴环丙基，2-氟-2-氯环丙基，2-氯-2-溴环丙基，2，2，3，3-四氟环丙基，2，2，3，3-四氯环丙基，五氟环丙基，氟环丁基，氯环丁基，2，2-二氟环丁基，2，2，3，3-四氟环丁基，2，2，3-三氟-3-氯环丁基，2，2-二氯-3，3-二氟环丁基，氟环戊基，二氟环戊基，氯环戊基，全氟环戊基，氯环己基和五氯环己基。Halocycloalkyl groups suitable as substituents are, for example, mono-, di- or per-halocycloalkyl groups, such as fluorocyclopropyl, chlorocyclopropyl, bromocyclopropyl, 2,2-dichloro Cyclopropyl, 2,2-difluorocyclopropyl, 2,2-dibromocyclopropyl, 2-fluoro-2-chlorocyclopropyl, 2-chloro-2-bromocyclopropyl, 2,2, 3,3-tetrafluorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, pentafluorocyclopropyl, fluorocyclobutyl, chlorocyclobutyl, 2,2-difluorocyclobutyl, 2,2,3,3-tetrafluorocyclobutyl, 2,2,3-trifluoro-3-chlorocyclobutyl, 2,2-dichloro-3,3-difluorocyclobutyl, fluorocyclopentyl difluorocyclopentyl, chlorocyclopentyl, perfluorocyclopentyl, chlorocyclohexyl and pentachlorocyclohexyl.

烷硫基是，例如，甲硫基，乙硫基，丙硫基或丁硫基或其支化异构体。Alkylthio is, for example, methylthio, ethylthio, propylthio or butylthio or branched isomers thereof.

苯基本身，或作为取代基的一部分，例如，苯硫基或苯甲酰氧基，可以是未取代或取代的，在这种情况下取代基可以在邻-，间-或对-位。除非另有说明，取代基是，例如，C1-C4烷基，C1-C4烷氧基，卤素或C1-C4卤代烷基。Phenyl by itself, or as part of a substituent, eg, thiophenyl or benzoyloxy, may be unsubstituted or substituted, in which case the substituent may be in the ortho-, meta- or para-position. Unless otherwise stated, substituents are, for example, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or C 1 -C 4 haloalkyl.

相应含义也适用于相结合的定义中的取代基，例如，烷基-S(O)-，烷基-ON＝CH-，(烷基)2NCO-，链烯基-SO-，炔基-S(O)n2-，烷基羰基氧基-，卤代烷氧基羰基-，卤代烷基-S(O)2O-，卤代烷基-SO-，(烷基)2NS(O)2-，烷基-S(O)2O-，被未取代或R17-取代的苯基所取代的烷基，被未取代或R17-取代的苯基所取代的链烯基，烷基-S(O)2NH-，卤代烷基-S(O)2NH-，烷基NHS(O)2-，烷基NHCO-，卤代烷基NHCO-，(烷基)2NCS-，H(烷氧基)P(O)O-，烷基(烷氧基)P(O)O-，(烷氧基)2P(O)O-，烷氧基羰基-链烯基，被未取代或R17-取代的苯基所取代的烷基-S(O)n2，烷氧基-烷基-S(O)n2-和炔基-S(O)n2-。Corresponding meanings also apply to the substituents in the combined definitions, e.g. alkyl-S(O)-, alkyl-ON=CH-, (alkyl) 2NCO- , alkenyl-SO-, alkynyl -S(O) n2 -, alkylcarbonyloxy-, haloalkoxycarbonyl-, haloalkyl-S(O) 2 O-, haloalkyl-SO-, (alkyl) 2 NS(O) 2 -, Alkyl-S(O) 2 O-, alkyl substituted by unsubstituted or R 17 -substituted phenyl, alkenyl substituted by unsubstituted or R 17 -substituted phenyl, alkyl-S (O) 2 NH-, Haloalkyl-S(O) 2 NH-, Alkyl NHS(O) 2 -, Alkyl NHCO-, Haloalkyl NHCO-, (Alkyl) 2 NCS-, H(Alkoxy )P(O)O-, alkyl(alkoxy)P(O)O-, (alkoxy) 2P (O)O-, alkoxycarbonyl-alkenyl, unsubstituted or R 17 -substituted phenyl-substituted alkyl-S(O) n2 , alkoxy-alkyl-S(O) n2- and alkynyl-S(O) n2- .

在氰基烷基，烷基羰基，烷氧基羰基链烯基，烷基羰基氧基，烷氧基羰基，烷氧基羰基氧基和卤代烷氧基羰基的定义中，在每种情况下给出的碳原子数的上限和下限不包括氰基或羰基碳原子，根据具体情况。In the definitions of cyanoalkyl, alkylcarbonyl, alkoxycarbonylalkenyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy and haloalkoxycarbonyl, give in each case The upper and lower limits given for the number of carbon atoms do not include cyano or carbonyl carbon atoms, as the case may be.

其中Q是基团Q1至Q4和R8为OH的通式I化合物能够是以下异构体形式I1-I4和Ic的混合物形式：

Figure A9880674200171
在式I1-I4和Ic的以上异构体化合物中：当Z1＝C(R6)R7，Z2＝(W)n6，Z3＝C(R6)R7和n4＝0时，异构体化合物的右手部分表示基团Q1；当Z1＝CH，Z2＝O，S或-(CH2)n5-，Z3＝CH和n4＝2时，异构体化合物的右手部分表示基团Q2；当Z1＝CH2，Z2＝CHNHR9，Z3＝CH2和n4＝O时，异构体化合物的右手部分表示基团Q3；或或当Z1＝NR10，Z2＝O，Z3＝C(R6)R7和n4＝0时，异构体化合物的右手部分表示基团Q4。Compounds of general formula I in which Q is a group Q1 to Q4 and R8 is OH can be in the form of a mixture of the following isomeric forms I1 - I4 and Ic:
Figure A9880674200171
Among the above isomer compounds of formulas I 1 -I 4 and Ic: when Z 1 =C(R 6 )R 7 , Z 2 =(W) n6 , Z 3 =C(R 6 )R 7 and n 4 =0, the right-hand part of the isomer compound represents the group Q 1 ; when Z 1 =CH, Z 2 =O, S or -(CH 2 ) n5 -, Z 3 =CH and n 4 =2, the isomeric The right-hand part of the isomer compound represents the group Q2 ; when Z1 = CH2 , Z2 = CHNHR9 , Z3 = CH2 and n4 =O, the right-hand part of the isomer compound represents the group Q3 ; Or or when Z 1 =NR 10 , Z 2 =O, Z 3 =C(R 6 )R 7 and n 4 =0, the right-hand part of the isomeric compound represents the group Q 4 .

其中Q是基团Q5的通式I化合物也可以是以下异构体形式I6，I7和Ie的混合物形式： Compounds of general formula I in which Q is a group Q5 may also be in the form of mixtures of the following isomeric forms I6 , I7 and Ie:

本发明包括所有这些异构体形式I1-I4，Ic，I6，I7和Ie以及它们的混合物I1至I4和Ic，和I6，I7和Ie。The present invention includes all these isomeric forms I 1 -I 4 , I c , I 6 , I 7 and Ie and mixtures thereof I 1 to I 4 and Ic, and I 6 , I 7 and Ie.

本发明同样包括盐类，即具有叠氮化物氢的通式I化合物，例如式I3和I6 的化合物，和具有羧酸和磺酰胺基团(例如羧基取代的苯基，烷基-S(O)2NH和卤代烷基-S(O)2NH基团)的衍生物能够与碱形成的盐。这些盐类例如是碱金属盐类，例如钠和钾盐；碱土金属盐类，例如钙盐和镁盐；铵盐，即未取代的铵盐和单-或多-取代的铵盐，例如三乙基铵盐和甲基铵盐；或与其他有机碱的盐类。The invention also includes salts, i.e. compounds of general formula I having an azide hydrogen, for example formulas I3 and I6 compounds, and derivatives with carboxylic acid and sulfonamide groups (such as carboxy-substituted phenyl, alkyl-S(O) 2NH and haloalkyl-S(O) 2NH groups) capable of forming with bases Salt. Such salts are, for example, alkali metal salts, such as sodium and potassium; alkaline earth metal salts, such as calcium and magnesium; ammonium salts, i.e. unsubstituted ammonium salts and mono- or poly-substituted ammonium salts, such as tris Ethylammonium and methylammonium salts; or salts with other organic bases.

在作为成盐物的碱金属和碱土金属氢氧化物中，可考虑锂、钠、钾、镁和钙的氢氧化物；但优选钠和钾的氢氧化物。合适的成盐物描述在例如WO97/41112中。Among the alkali metal and alkaline earth metal hydroxides as salt formers, lithium, sodium, potassium, magnesium and calcium hydroxides come into consideration; however, sodium and potassium hydroxides are preferred. Suitable salt formers are described, for example, in WO97/41112.

在碱金属和碱土金属氢化物中，可考虑氢化钠和氢化钙，对于碳酸盐，可考虑钠、钾、铯、钙、钡、镁和锂的碳酸盐。Among the alkali metal and alkaline earth metal hydrides, sodium hydride and calcium hydride come into consideration, and as carbonates, sodium, potassium, cesium, calcium, barium, magnesium and lithium carbonates come into consideration.

适合形成铵盐的胺的实例包括氨以及伯，仲和叔C1-C18烷基胺类，C1-C4羟基烷基胺类和C2-C4烷氧基烷基胺类，例如甲基胺，乙基胺，正丙基胺，异丙基胺，丁基胺的四种异构体，正戊基胺，异戊基胺，己基胺，庚基胺，辛基胺，壬基胺，癸基胺，十五烷基胺，十六烷基胺，十七烷基胺，十八烷基胺，甲基乙基胺，甲基异丙基胺，甲基己基胺，甲基壬基胺，甲基十五烷基胺，甲基十八烷基胺，乙基丁基胺，乙基庚基胺，乙基辛基胺，己基庚基胺，己基辛基胺，二甲基胺，二乙基胺，二-正丙基胺，二异丙基胺，二-正丁基胺，二-正戊基胺，二异戊基胺，二己基胺，二庚基胺，二辛基胺，乙醇胺，正丙醇胺，异丙醇胺，N，N-二乙醇胺，N-乙基丙醇胺，N-丁基乙醇胺，烯丙基胺，正丁烯基-2-胺，正戊烯基-2-胺，2，3-二甲基丁烯基-2-胺，二丁烯基-2-胺，正己烯基-2-胺，丙二胺，三甲基胺，三乙基胺，三-正丙基胺，三异丙基胺，三-正丁基胺，三异丁基胺，三-仲丁基胺，三-正戊基胺，甲氧基乙基胺和乙氧基乙基胺；杂环胺类，例如吡啶，喹啉，异喹啉，吗啉，硫代吗啉，哌啶，吡咯烷，二氢吲哚，奎宁环和吖庚因；伯芳基胺类，例如苯胺类，甲氧基苯胺类，乙氧基苯胺类，o-，m-和p-甲苯胺类，苯二胺类，联苯胺类，萘胺类和o-，m-和p-氯苯胺类；但优选三乙基胺，异丙基胺和二异丙基胺。Examples of amines suitable for the formation of ammonium salts include ammonia and primary, secondary and tertiary C1 - C18 alkylamines, C1 - C4 hydroxyalkylamines and C2 - C4 alkoxyalkylamines, For example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomers of butylamine, n-pentylamine, isopentylamine, hexylamine, heptylamine, octylamine, Nonylamine, Decylamine, Pentadecylamine, Hexadecylamine, Heptadecylamine, Octadecylamine, Methylethylamine, Methylisopropylamine, Methylhexylamine, Methylnonylamine, Methylpentadecylamine, Methyloctadecylamine, Ethylbutylamine, Ethylheptylamine, Ethyloctylamine, Hexylheptylamine, Hexyloctylamine, Dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-pentylamine, diisoamylamine, dihexylamine, diheptylamine Amine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl- 2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, tris Methylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-pentylamine, methylamine Oxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepines; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but triethylamine, isopropylamine and diisopropylamine are preferred.

在R6，R7或R17的定义中具有碱性基团，尤其具有碱性氨基，例如烷基氨基和二烷基氨基的通式I化合物的盐类是，例如，与无机或有机酸，例如氢卤酸如氢氟酸、盐酸、氢溴酸或氢碘酸，及硫酸，磷酸，硝酸，和有机酸类，如乙酸，三氟乙酸，三氯乙酸，丙酸，乙醇酸，硫氰酸，柠檬酸，苯甲酸，草酸，甲酸，苯磺酸，对-甲苯磺酸，和甲烷磺酸形成的盐类。Salts of compounds of the general formula I with basic groups in the definition of R 6 , R 7 or R 17 , especially basic amino groups, such as alkylamino and dialkylamino groups, are, for example, with inorganic or organic acids , such as hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, and sulfuric acid, phosphoric acid, nitric acid, and organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, sulfur Salts of cyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid, and methanesulfonic acid.

至少一个不对称碳原子在通式I化合物中，例如在取代基R1(其中R1是支化烷基，链烯基，卤代烷基或烷氧基烷基或其中R1和R2和/或R3和R4，及R6和R7互不相同)中存在的可能性意味着该化合物能够以旋光活性的单一异构体存在或以外消旋混合物形式存在。 At least one asymmetric carbon atom is in the compound of general formula I , for example in the substituent R or R 3 and R 4 , and R 6 and R 7 are different from each other) means that the compound can exist as an optically active single isomer or as a racemic mixture.

因为在苯甲酰基和Q1至Q6环体系之间的旋转受阻，通式I化合物也能够以旋转异构体(阻转异构体(atropisomer))形式存在。Because of the hindered rotation between the benzoyl group and the Q1 to Q6 ring system, compounds of the general formula I can also exist in the form of rotational isomers (atropisomers).

在本发明中，“通式I化合物”被理解为包括纯旋光对映体和外消旋体或非对映异构体和阻转异构体。In the present invention, "compounds of general formula I" are understood to include pure optical enantiomers and racemates or diastereomers and atropisomers.

当存在脂族C＝C或C＝N-O双键(syn/anti)时，可存在几何异构现象。本发明还涉及这些异构体。Geometric isomerism can exist when aliphatic C=C or C=N-O double bonds (syn/anti) are present. The present invention also relates to these isomers.

优选满足以下条件的通式I化合物：其中R1是C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基-C1-C4烷基，C1-C4烷氧基羰基，氰基，氰基-C1-C4烷基，CHO，C1-C4烷基-ON＝CH，C2-C6链烯基，C1-C4烷氧基羰基-C2-C6链烯基或基团-CH(OR20)OR21；W是氧，硫，-C(R18)2-或-N(R22)-；各R18独立地是氢，C1-C4烷基或C1-C4烷氧基羰基；和R22是氢，C1-C4烷基或C1-C4烷氧基羰基。Preferred are compounds of general formula I satisfying the following conditions: wherein R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 - C 4 alkoxycarbonyl, cyano, cyano- C 1 -C 4 alkyl, CHO, C 1 -C 4 alkyl-ON=CH, C 2 -C 6 alkenyl, C 1 -C 4 alkane Oxycarbonyl-C 2 -C 6 alkenyl or group -CH(OR 20 )OR 21 ; W is oxygen, sulfur, -C(R 18 ) 2 -or -N(R 22 )-; each R 18 independently hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl; and R 22 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl.

也优选的是满足以下条件的通式I化合物：其中Q是基团

Figure A9880674200201
R6和R7各自独立地是C1-C4烷基或C1-C4烷基-S(O)n2；n2是O；R8是OH，C1-C4烷氧基，C1-C4烷基羰基氧基，苯硫基或C1-C4烷硫基；R10，R11和R12各自独立地是氢，C1-C4烷基或C1-C4烷氧基羰基；R13是卤素，C1-C4烷基，C3-C6环烷基，COOR16，COR15或氰基；R14是C1-C4烷基，C3-C6炔基，C3-C6环烷基或被卤素，C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基或苯基取代的C3-C6环烷基；R15是C1-C4烷基，C1-C4卤代烷基，C3-C6链烯基，C3-C6卤代链烯基，C3-C6炔基，C3-C6卤代炔基或苯基；以及R16和Y如通式I中所定义。Also preferred are compounds of general formula I where Q is a group
Figure A9880674200201
R 6 and R 7 are each independently C 1 -C 4 alkyl or C 1 -C 4 alkyl-S(O) n2 ; n 2 is O; R 8 is OH, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyloxy, phenylthio or C 1 -C 4 alkylthio; R 10 , R 11 and R 12 are each independently hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl; R 13 is halogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, COOR 16 , COR 15 or cyano; R 14 is C 1 -C 4 alkyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl or halogenated, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 halo Alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl or phenyl substituted C 3 -C 6 cycloalkyl; R 15 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl or phenyl; and R 16 and Y as defined in Formula I.

也优选的是满足以下条件的通式I化合物：其中Q为基团

Figure A9880674200211
R6和R7相互独立地是C1-C4烷基或C1-C4烷基-S(O)n2；n2是O；R8是OH，C1-C4烷氧基，C1-C4烷基羰基氧基，苯硫基或C1-C4烷硫基；W是氧或-C(R18)2-；R18是氢；n6是1；和R9是(C1-C4烷基)-NHCO或(C1-C4烷基)2NCO。Also preferred are compounds of general formula I that satisfy the following conditions: wherein Q is a group
Figure A9880674200211
R 6 and R 7 are independently C 1 -C 4 alkyl or C 1 -C 4 alkyl-S(O) n2 ; n 2 is O; R 8 is OH, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyloxy, phenylthio or C 1 -C 4 alkylthio; W is oxygen or -C(R 18 ) 2 -; R 18 is hydrogen; n 6 is 1; and R 9 is (C 1 -C 4 alkyl)-NHCO or (C 1 -C 4 alkyl) 2 NCO.

还优选其中n为1或2的通式I化合物。Preference is also given to compounds of the general formula I in which n is 1 or 2.

根据本发明的制备通式I化合物的方法

Figure A9880674200212
其中R1-R5和n如通式I中所定义，Q是基团
Figure A9880674200213
Figure A9880674200214
R8是OH；以及R6，R7，R9，R10，W，n6和Y如通式I中所定义，是按照与已知方法类似的方式进行的，并包括a)让通式III的化合物
Figure A9880674200215
其中R1-R5和n如前所定义和X是离去基团，例如卤素，在惰性有机溶剂中在碱存在下与通式IV的化合物反应
Figure A9880674200221
其中Z1是C(R6)R7，Z2是(W)n6，Z3是C(R6)R7和n4是0(＝基团Q1)；Z1是CH，Z2是氧，硫或-(CH2)n5-(＝Y)，Z3是CH和n4是2(＝基团Q2)；Z1是CH2，Z2是CHNHR9，Z3是CH2和n4是O(＝基团Q3)；或Z1是NR10，Z2是氧，Z3是C(R6)R7和n4是O(＝基团Q4)，和R6，R7，R9，R10，W，n6和n5如通式I中所定义，形成通式Ic的化合物：
Figure A9880674200222
和然后将该化合物在例如碱和催化量的氰化物源存在下异构化；或b)让通式Id的化合物其中R1-R5和n如前所定义，与通式IV的化合物，
Figure A9880674200224
其中Z1，Z2，Z3和n4如前所定义，在惰性有机溶剂中在碱和偶联剂存在下进行反应，形成通式Ic的化合物：
Figure A9880674200231
然后，按照路径a)中所述将该化合物异构化。According to the method for the preparation of compounds of general formula I of the present invention
Figure A9880674200212
wherein R 1 -R 5 and n are as defined in general formula I, Q is the group
Figure A9880674200213
Figure A9880674200214
R 8 is OH; and R 6 , R 7 , R 9 , R 10 , W, n 6 and Y are as defined in general formula I, carried out in a manner similar to known methods and including a) allowing Compound of formula III
Figure A9880674200215
wherein R1 - R5 and n are as previously defined and X is a leaving group, such as a halogen, reacted with a compound of general formula IV in the presence of a base in an inert organic solvent
Figure A9880674200221
where Z 1 is C(R 6 )R 7 , Z 2 is (W) n6 , Z 3 is C(R 6 )R 7 and n 4 is 0 (=group Q 1 ); Z 1 is CH, Z 2 is oxygen, sulfur or -(CH 2 ) n5 -(=Y), Z 3 is CH and n 4 is 2 (=group Q 2 ); Z 1 is CH 2 , Z 2 is CHNHR 9 , Z 3 is CH 2 and n 4 are O (=group Q 3 ); or Z 1 is NR 10 , Z 2 is oxygen, Z 3 is C(R 6 )R 7 and n 4 is O (=group Q 4 ), and R 6 , R 7 , R 9 , R 10 , W, n 6 and n 5 are as defined in general formula I, forming a compound of general formula Ic:
Figure A9880674200222
and then isomerizing the compound in the presence of, for example, a base and a catalytic amount of a cyanide source; or b) allowing the compound of general formula Id Wherein R 1 -R 5 and n are as previously defined, and the compound of general formula IV,
Figure A9880674200224
Wherein Z 1 , Z 2 , Z 3 and n 4 are as defined above, react in the presence of a base and a coupling agent in an inert organic solvent to form a compound of general formula Ic:
Figure A9880674200231
This compound is then isomerized as described in route a).

根据本发明的制备通式I化合物的方法

Figure A9880674200232
其中R1-R5和n如通式I中所定义，Q是基团 以及R11和R12如通式I中所定义，是按照与已知方法类似的方式进行的，并包括c)让通式III的化合物
Figure A9880674200234
其中R1-R5和n如前所定义和X是离去基团，例如卤素，在惰性有机溶剂中在碱存在下与通式IVa的化合物反应
Figure A9880674200235
其中R11和R12如前所定义，形成通式Ie的化合物：
Figure A9880674200241
和然后将该化合物在例如碱和催化量的氰化物源存在下异构化；或b)让通式Id的化合物
Figure A9880674200242
其中R1-R5和n如前所定义，与通式IVa的化合物，其中R11和R12如前所定义，在惰性有机溶剂中在碱和偶联剂存在下进行反应，形成通式Ie的化合物：然后，按照路径a)中所述将该化合物异构化。According to the method for the preparation of compounds of general formula I of the present invention
Figure A9880674200232
wherein R 1 -R 5 and n are as defined in general formula I, Q is the group and R 11 and R 12 are as defined in general formula I, are carried out in a manner similar to known methods, and include c) letting the compound of general formula III
Figure A9880674200234
wherein R1 - R5 and n are as previously defined and X is a leaving group, such as a halogen, reacted with a compound of general formula IVa in the presence of a base in an inert organic solvent
Figure A9880674200235
wherein R 11 and R 12 are as defined previously, forming compounds of general formula Ie:
Figure A9880674200241
and then isomerizing the compound in the presence of, for example, a base and a catalytic amount of a cyanide source; or b) allowing the compound of general formula Id
Figure A9880674200242
Wherein R 1 -R 5 and n are as previously defined, and the compound of general formula IVa, Wherein R 11 and R 12 are as previously defined, react in the presence of a base and a coupling agent in an inert organic solvent to form a compound of general formula Ie: This compound is then isomerized as described in route a).

根据本发明的制备通式I化合物的方法其中R1-R5和n如通式I中所定义，Q是基团

Figure A9880674200246
R13是氢，C1-C4烷基，被未取代或R17-取代的苯基所取代的C1-C4烷基，C1-C4卤代烷基，C2-C6链烯基，被未取代或R17-取代的苯基所取代的C2-C6链烯基，C2-C6炔基，被未取代或R17-取代的苯基所取代的C2-C6炔基，C3-C6卤代链烯基，C3-C6卤代炔基，C3-C6环烷基，被卤素，R15或COOR16取代的C3-C6环烷基；C1-C4烷基-S(O)n2，被未取代或R17取代的苯基所取代的C1-C4烷基-S(O)n2，C1-C4烷氧基-C2-C6烷基-S(O)n2，C2-C6链烯基-S(O)n2，被未取代或R17-取代的苯基所取代的C2-C6链烯基-S(O)n2，C2-C6炔基-S(O)n2或被未取代或R17-取代的苯基所取代C2-C6炔基S(O)n2；和R14-R17和n2如通式I中所定义，是按照与已知方法类似的方式进行的，并包括：a)将通式V的化合物其中R1-R5，R14和n如前所定义，在碱、二硫化碳和通式VI的烷基化试剂：R25-X1(VI)，其中R25是C1-C4烷基，被未取代或R17-取代的苯基所取代的C1-C4烷基，C1-C4烷氧基-C2-C6烷基，C2-C6链烯基，被未取代或R17取代的苯基所取代的C2-C6链烯基，C2-C6炔基或被未取代或R17取代的苯基所取代的C2-C6炔基；R17如通式I中所定义，和X1是离去基团，例如卤素或磺酸根，存在下转化成式VII的化合物：
Figure A9880674200252
其中R1-R5，R14，R25和n如前所定义，然后用羟基胺盐酸盐在碱存在下，任意性地在溶剂中，将该化合物环化而形成通式If的化合物：
Figure A9880674200261
其中R1-R5，R14和n如前所定义，R13是R25S和R25是C1-C4烷基，被未取代或R17-取代的苯基所取代的C1-C4烷基，C1-C4烷氧基-C2-C6烷基，C2-C6链烯基，被未取代或R17-取代的苯基所取代的C2-C6链烯基，C2-C6炔基或被未取代或R17-取代的苯基所取代的C2-C6炔基，和然后用例如间-氯过苯甲酸(m-CPBA)将该化合物氧化；或b)用通式VIII的原酸酰胺
Figure A9880674200262
其中R13是氢，C1-C4烷基，被未取代或R17取代的苯基所取代的C1-C4烷基，C1-C4卤代烷基，C2-C6链烯基，被未取代或R17-取代的苯基所取代的C2-C6链烯基，C2-C6炔基，被未取代或R17取代的苯基所取代的C2-C6炔基，C3-C6卤代链烯基，C3-C6卤代炔基，C3-C6环烷基或被卤素，R15或COOR16所取代的C3-C6环烷基；R15-R17如通式I中所定义；和R26和R27相互独立地是C1-C4烷基，将通式V的化合物
Figure A9880674200263
其中R1-R5，R14和n如前所定义，转化成通式IX的化合物：
Figure A9880674200264
其中R1-R5，R13，R14，n和R27如以上所定义，和然后在羟基胺盐酸盐存在下，任选在溶剂中，在碱存在下将该化合物环化，形成通式If的化合物：根据本发明的制备通式Id的化合物的方法，
Figure A9880674200272
其中R1，R3-R5和n如通式I中所定义和R2是CH3，与已知方法类似地进行并包括：a)用通式XXV的化合物其中R1，R3和R4如通式I中所定义，和Hal是卤素，将通式XX的化合物加以醚化，
Figure A9880674200274
其中R5如通式I中所定义以及R28是C1-C4烷基，形成通式XXI的化合物：
Figure A9880674200275
其中R1，R3-R5和R28如以上所定义，让该化合物进行Claisen重排和然后用通式XXVI的化合物：
Figure A9880674200281
其中Hal是氯、溴或碘将所得通式XXII的化合物加以酰化而得到通式XXIII的化合物，
Figure A9880674200283
该化合物进行重排并得到通式XXIV的化合物：
Figure A9880674200284
然后将该化合物水解和环化而形成通式Id的化合物
Figure A9880674200285
其中R1和R3-R5如以上所定义，R2是CH3和n为O，然后将该化合物氧化(n是1或2)；或b)首先将通式XX的化合物溴化，
Figure A9880674200291
其中R5和R28如以上所定义，得到通式XXb的化合物
Figure A9880674200292
在催化剂和通式XXVb的有机金属试剂存在下让该化合物进行偶联反应，其中R1，R3和R4如以上所定义和R29是C1-C4烷基，得到通式XXII的化合物：其中R1，R3-R5和R28如以上所定义，然后与路径a)所述方法类似地让该化合物进一步反应而形成通式Id的化合物。According to the method for the preparation of compounds of general formula I of the present invention wherein R 1 -R 5 and n are as defined in general formula I, Q is the group
Figure A9880674200246
R 13 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted by unsubstituted or R 17 -substituted phenyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl C 2 -C 6 alkenyl substituted by unsubstituted or R 17 -substituted phenyl, C 2 -C 6 alkynyl, C 2 -substituted by unsubstituted or R 17 -substituted phenyl C 6 alkynyl, C 3 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 substituted by halogen, R 15 or COOR 16 Cycloalkyl; C 1 -C 4 alkyl-S(O) n2 , C 1 -C 4 alkyl-S(O) n2 substituted by unsubstituted or R 17 substituted phenyl, C 1 -C 4 Alkoxy-C 2 -C 6 alkyl-S(O) n2 , C 2 -C 6 alkenyl-S(O) n2 , C 2 -substituted by unsubstituted or R 17 -substituted phenyl C 6 alkenyl-S(O) n2 , C 2 -C 6 alkynyl-S(O) n2 or C 2 -C 6 alkynyl S(O) substituted by unsubstituted or R 17 -substituted phenyl n2 ; and R 14 -R 17 and n 2 are as defined in general formula I, and are carried out in a manner similar to known methods, and include: a) compounding the compound of general formula V Wherein R 1 -R 5 , R 14 and n are as defined above, in base, carbon disulfide and the alkylating agent of general formula VI: R 25 -X 1 (VI), wherein R 25 is C 1 -C 4 alkyl , C 1 -C 4 alkyl substituted by unsubstituted or R 17 -substituted phenyl, C 1 -C 4 alkoxy-C 2 -C 6 alkyl, C 2 -C 6 alkenyl, by C 2 -C 6 alkenyl, C 2 -C 6 alkynyl substituted by unsubstituted or R 17 substituted phenyl or C 2 -C 6 alkynyl substituted by unsubstituted or R 17 substituted phenyl; R 17 is as defined in general formula I, and X 1 is a leaving group, such as a halogen or sulfonate, in the presence of conversion to a compound of formula VII:
Figure A9880674200252
wherein R 1 -R 5 , R 14 , R 25 and n are as defined above, then the compound is cyclized with hydroxylamine hydrochloride in the presence of a base, optionally in a solvent, to form a compound of the general formula If :
Figure A9880674200261
wherein R 1 -R 5 , R 14 and n are as defined above, R 13 is R 25 S and R 25 is C 1 -C 4 alkyl, C 1 substituted by unsubstituted or R 17 -substituted phenyl -C 4 alkyl, C 1 -C 4 alkoxy-C 2 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C substituted by unsubstituted or R 17 -substituted phenyl 6 alkenyl, C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by unsubstituted or R 17 -substituted phenyl, and then with e.g. m-chloroperbenzoic acid (m-CPBA) Oxidation of the compound; or b) with the orthoamide of general formula VIII
Figure A9880674200262
wherein R 13 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted by unsubstituted or R 17 substituted phenyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenes C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C substituted by unsubstituted or R 17 -substituted phenyl, C 2 -C substituted by unsubstituted or R 17 -substituted phenyl 6 alkynyl, C 3 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl or C 3 -C 6 substituted by halogen, R 15 or COOR 16 Cycloalkyl; R 15 -R 17 are as defined in general formula I; and R 26 and R 27 are C 1 -C 4 alkyl independently of each other, the compound of general formula V
Figure A9880674200263
Wherein R 1 -R 5 , R 14 and n are as previously defined, converted into compounds of general formula IX:
Figure A9880674200264
wherein R 1 -R 5 , R 13 , R 14 , n and R 27 are as defined above, and the compound is then cyclized in the presence of hydroxylamine hydrochloride, optionally in a solvent, in the presence of a base to form Compounds of the general formula If: According to the method for preparing the compound of general formula Id of the present invention,
Figure A9880674200272
wherein R 1 , R 3 -R 5 and n are as defined in general formula I and R 2 is CH 3 , proceed analogously to known methods and include: a) using a compound of general formula XXV wherein R 1 , R 3 and R 4 are as defined in general formula I, and Hal is a halogen, the compound of general formula XX is etherified,
Figure A9880674200274
wherein R 5 is as defined in general formula I and R 28 is C 1 -C 4 alkyl, forming compounds of general formula XXI:
Figure A9880674200275
wherein R 1 , R 3 -R 5 and R 28 are as defined above, subjecting the compound to a Claisen rearrangement and then using a compound of general formula XXVI:
Figure A9880674200281
Wherein Hal is chlorine, bromine or iodine and the compound of general formula XXII obtained is acylated to give a compound of general formula XXIII,
Figure A9880674200283
This compound undergoes rearrangement and gives compounds of general formula XXIV:
Figure A9880674200284
This compound is then hydrolyzed and cyclized to form compounds of general formula Id
Figure A9880674200285
wherein R 1 and R 3 -R 5 are as defined above, R 2 is CH 3 and n is O, then the compound is oxidized (n is 1 or 2); or b) the compound of general formula XX is first brominated,
Figure A9880674200291
wherein R and R are as defined above, yielding compounds of general formula XXb
Figure A9880674200292
Allowing the compound to undergo a coupling reaction in the presence of a catalyst and an organometallic reagent of general formula XXVb, wherein R 1 , R 3 and R 4 are as defined above and R 29 is C 1 -C 4 alkyl, yielding compounds of general formula XXII: wherein R 1 , R 3 -R 5 and R 28 are as defined above, then the compound is further reacted analogously to the method described in route a) to form a compound of general formula Id.

根据本发明的制备通式Id化合物的方法，

Figure A9880674200295
其中R1，R3-R5和n如通式I中所定义以及R2是CH3，与已知方法类似地进行并包括让通式XXa的化合物
Figure A9880674200296
其中R5如前所定义和R28是C1-C4烷基，与通式XXVa的化合物反应其中R1，R3和R4如前所定义，得到通式XXIa的化合物让该化合物进行Claisen重排，得到通式XXIIa的化合物：
Figure A9880674200303
它然后进行水解和环化而形成通式Id的化合物：其中R1和R3-R5如前所定义，R2是CH3和n是O，然后将该化合物氧化(n是1或2)。According to the method for preparing the compound of general formula Id of the present invention,
Figure A9880674200295
wherein R 1 , R 3 -R 5 and n are as defined in general formula I and R 2 is CH 3 , carried out analogously to known methods and comprising letting compounds of general formula XXa
Figure A9880674200296
wherein R 5 is as previously defined and R 28 is C 1 -C 4 alkyl, reacted with a compound of general formula XXVa wherein R 1 , R 3 and R 4 are as defined previously, yielding compounds of general formula XXIa Subjecting this compound to a Claisen rearrangement affords compounds of general formula XXIIa:
Figure A9880674200303
It then undergoes hydrolysis and cyclization to form compounds of general formula Id: wherein R 1 and R 3 -R 5 are as defined before, R 2 is CH 3 and n is O, and the compound is then oxidized (n is 1 or 2).

根据本发明的制备通式I化合物的方法，

Figure A9880674200305
其中R1-R5和n如通式I中所定义和Q是卤素，与已知方法类似地进行并包括用卤化试剂处理通式Id的化合物，
Figure A9880674200311
其中R1-R5和n如以上所定义。According to the method for preparing the compound of general formula I of the present invention,
Figure A9880674200305
wherein R 1 -R 5 and n are as defined in general formula I and Q is a halogen, carried out analogously to known methods and comprising treating a compound of general formula Id with a halogenating reagent,
Figure A9880674200311
wherein R 1 -R 5 and n are as defined above.

在下面的反应方案1-6中更详细地说明通式I化合物的制备。反应方案1路径a)：

Figure A9880674200321
路径b)： The preparation of compounds of general formula I is illustrated in more detail in Reaction Schemes 1-6 below. Reaction scheme 1 path a):
Figure A9880674200321
Path b):

在反应方案1中当Z1＝C(R6)R7，Z2＝(W)n6，Z3＝C(R6)(R7)和n4＝O时，通式I的化合物的右手部分表示基团Q1；当Z1＝CH，Z2＝O，S或-(CH2)n5-，Z3＝CH和n4＝2时，通式I的化合物的右手部分表示基团Q2；当Z1＝CH2，Z2＝CHNHR9，Z3＝CH2和n4＝O时，通式I的化合物的右手部分表示基团Q3；或当Z1＝NH10，Z2＝O，Z3＝C(R6)R7和n4＝O时，通式I的化合物的右手部分表示基团Q4。反应方案2路径a)：

Figure A9880674200341
路径b)：
Figure A9880674200342
反应方案3路径a)：
Figure A9880674200351
Figure A9880674200352
If(R13＝R25SO-或R25SO2-)路径b)：
Figure A9880674200353
In Reaction Scheme 1, when Z 1 =C(R 6 )R 7 , Z 2 =(W) n6 , Z 3 =C(R 6 )(R 7 ) and n 4 =O, the compound of general formula I The right-hand part represents the group Q1 ; when Z1 =CH, Z2 =O, S or -( CH2 ) n5- , Z3 =CH and n4 =2, the right-hand part of the compound of general formula I represents the group Group Q 2 ; when Z 1 ＝CH 2 , Z 2 ＝CHNHR 9 , Z 3 ＝CH 2 and n 4 ＝O, the right-hand part of the compound of general formula I represents the group Q 3 ; or when Z 1 ＝NH 10 , Z 2 ═O, Z 3 ═C(R 6 )R 7 and n 4 ═O, the right-hand part of the compound of general formula I represents the group Q 4 . Reaction scheme 2 path a):
Figure A9880674200341
Path b):
Figure A9880674200342
Reaction scheme 3 path a):
Figure A9880674200351
Figure A9880674200352
If (R 13 =R 25 SO- or R 25 SO 2 -) path b):
Figure A9880674200353

对于其中Q是基团Q1-Q4和R8是OH的通式I化合物的制备(根据反应方案1，路径a))，所使用的起始原料是满足以下条件的通式III的羧酸衍生物：其中X为离去基团例如卤素(例如碘，溴或尤其氯)，N-氧基邻苯二甲酰亚胺或N，O-二甲基羟基氨基或活化酯的一部分，例如

Figure A9880674200361
(从二环己基碳化二亚胺(DCC)和对应的羧酸形成)或
Figure A9880674200362
(从N-乙基-N′-(3-二甲基氨基丙基)碳化二亚胺(EDC)和对应的羧酸形成)。这些起始原料是在惰性有机溶剂，例如卤代烃类(例如二氯甲烷)，腈类(例如乙腈)，或芳族烃类(例如甲苯)的存在下和在碱如烷基胺类(例如三乙基胺)，芳族胺类(例如吡啶或4-二甲基氨基吡啶(DMAP))存在下与通式IV的二酮衍生物反应，形成通式Ic的异构化烯醇醚类。酯化在O-110℃的温度下进行。For the preparation of compounds of general formula I in which Q is a group Q1 - Q4 and R8 is OH (according to reaction scheme 1, path a)), the starting material used is a carboxyl group of general formula III satisfying the following conditions Acid derivatives: wherein X is part of a leaving group such as a halogen (e.g. iodine, bromine or especially chlorine), N-oxyphthalimide or N,O-dimethylhydroxylamino or an activated ester, For example
Figure A9880674200361
(formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or
Figure A9880674200362
(formed from N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) and the corresponding carboxylic acid). These starting materials are prepared in the presence of inert organic solvents such as halogenated hydrocarbons (such as dichloromethane), nitriles (such as acetonitrile), or aromatic hydrocarbons (such as toluene) and in the presence of bases such as alkylamines ( e.g. triethylamine), aromatic amines (e.g. pyridine or 4-dimethylaminopyridine (DMAP)) react with diketone derivatives of general formula IV in the presence of to form isomerized enol ethers of general formula Ic kind. Esterification is carried out at a temperature of 0-110°C.

通式Ic的酯衍生物异构化形成通式I(R8＝OH)的二酮衍生物例如能够在碱，例如烷基胺(例如三乙基胺)或碳酸盐(例如碳酸钾)，和催化量的氰化物源(例如丙酮合氰化氢或氰化钾)存在下与EP-A-0 369 803类似地进行。The isomerization of ester derivatives of general formula Ic to form diketone derivatives of general formula I (R 8 =OH) can for example , and in the presence of a catalytic amount of a cyanide source (eg acetone cyanohydrin or potassium cyanide) analogously to EP-A-0 369 803.

根据反应方案1，路径b)，通式I(R8＝OH)的所需二酮例如能够按照与Chem.Lett.1975，1045中类似的方法，在惰性溶剂，例如卤代烃(例如二氯甲烷)，腈(例如乙腈)或芳族烃(例如甲苯)中在碱例如烷基胺(如三乙基胺)和偶联剂(例如2-氯-1-甲基-吡啶鎓碘化物)存在下通过用通式IV的二酮衍生物将通式Id的羧酸加以酯化而获得。酯化(取决于所使用的溶剂)是在0-110℃之间的温度下进行的，首先(如路径a)所述)得到通式Ic的异构化酯，然后，例如在碱和催化量氰化物源存在下，按路径a)所述被异构化而形成通式I(R8＝OH)的所需二酮衍生物。According to reaction scheme 1, route b), the desired diketone of general formula I (R 8 =OH) can be, for example, in an inert solvent, such as a halogenated hydrocarbon (such as di Chloromethane), nitriles (such as acetonitrile) or aromatic hydrocarbons (such as toluene) in bases such as alkylamines (such as triethylamine) and coupling agents (such as 2-chloro-1-methyl-pyridinium iodide ) is obtained by esterification of a carboxylic acid of general formula Id with a diketone derivative of general formula IV in the presence of . Esterification (depending on the solvent used) is carried out at a temperature between 0-110° C., first (as described in route a)) to the isomerized ester of the general formula Ic, and then, for example, in the presence of base and catalysis The desired diketone derivatives of general formula I (R 8 =OH) are formed by isomerization as described in route a) in the presence of a small amount of cyanide source.

根据反应方案2，其中Q为基团Q5的通式I化合物能够按照与例如反应方案1或《四面体》36，2409(1976)中所述方法类似地获得：a) 在惰性有机溶剂中在碱存在下用通式IVa的羟基吡唑衍生物将通式III的羧酸衍生物加以酯化，或b) 在惰性溶剂中在碱和偶联剂存在下用通式IVa的羟基吡唑衍生物将通式Id的羧酸加以酯化，随后，例如借助于碱和催化量的氰化物源将中间形成的通式Ie的酯加以异构化。According to Reaction Scheme 2, the compound of general formula I wherein Q is group Q can be obtained according to the methods described in, for example, Reaction Scheme 1 or "Tetrahedron" 36, 2409 (1976): a) in an inert organic solvent Esterification of the carboxylic acid derivative of the general formula III with a hydroxypyrazole derivative of the general formula IVa in the presence of a base, or b) derivatization with a hydroxypyrazole of the general formula IVa in the presence of a base and a coupling agent in an inert solvent The esterification of the carboxylic acid of the general formula Id with the compound is followed by isomerization of the intermediately formed ester of the general formula Ie, for example by means of a base and a catalytic amount of a cyanide source.

其中Q是基团Q6的通式I化合物的制备能够根据反应方案3由以下两路径有利地进行：The preparation of compounds of general formula I wherein Q is a group Q can be advantageously carried out according to reaction scheme 3 by the following two routes:

由路径a)，例如与《合成》1991，301；ibid.1988，793或《四面体》32，3055(1976)类似地，让通式V的β-二酮衍生物与二硫化碳在碱，例如碳酸盐(碳酸钾)，金属氢化物(例如氢化钠)或氟化钾/铝，和通式VI的烷基化试剂存在下进行反应，在通式VI中X1是离去基团，例如卤素(例如碘，溴或尤其氯)，R25OSO2O-，CH3SO2O-或

Figure A9880674200371
。该反应有利地在溶剂，例如酰胺(例如N，N-二甲基甲酰胺(DMF))，亚砜(例如二甲基亚砜(DMSO))，或腈(例如乙腈)中进行。所得到的通式VII的乙烯酮缩硫代醇(ketene thioacetal)在碱例如乙酸钠存在下，在溶剂例如醇类(例如乙醇)或醚类(例如四氢呋喃)中用羟基胺盐酸盐加以环化而形成其中R13为R25S-的通式If化合物。该环化反应有利地在0-100℃之间的温度下进行。如果需要，通式If的化合物能够与已知的标准方法类似地用例如过酸(例如间-氯过苯甲酸(m-CPBA)或过乙酸)加以氧化而形成相应的通式If的砜或亚砜(R13＝R25SO-或R25SO2-)；或By route a), such as "synthesis"1991,301; ibid.1988,793 or "tetrahedron" 32,3055 (1976) similarly, let the β-diketone derivative of general formula V and carbon disulfide be in base, for example Carbonate (potassium carbonate), metal hydride (such as sodium hydride) or potassium fluoride/aluminum, reacts under the presence of the alkylating agent of general formula VI, in general formula VI X 1 is a leaving group, For example halogen (eg iodine, bromine or especially chlorine), R 25 OSO 2 O-, CH 3 SO 2 O- or
Figure A9880674200371
. The reaction is advantageously carried out in a solvent such as an amide such as N,N-dimethylformamide (DMF), a sulfoxide such as dimethylsulfoxide (DMSO), or a nitrile such as acetonitrile. The resulting ketene thioacetal of general formula VII is cyclized with hydroxylamine hydrochloride in a solvent such as alcohols (e.g. ethanol) or ethers (e.g. tetrahydrofuran) in the presence of a base such as sodium acetate. to form compounds of the general formula If wherein R 13 is R 25 S-. The cyclization reaction is advantageously carried out at a temperature between 0-100°C. If desired, compounds of the general formula If can be oxidized analogously to known standard methods with, for example, peracids such as m-chloroperbenzoic acid (m-CPBA) or peracetic acid to form the corresponding sulfones of the general formula If or Sulfoxide (R 13 =R 25 SO- or R 25 SO 2 -); or

由路径b)，与《杂环化学杂志》20，645(1983)类似地，用通式VIII的原酸酰胺(例如二甲基甲酰胺缩二甲醇)将通式V的β-二酮衍生物转化成通式IX的烯胺衍生物，然后在碱例如乙酸钠存在下在溶剂例如醇(例如乙醇)中用羟基胺盐酸盐将该衍生物加以环化而形成通式If的化合物。By route b), similar to "Journal of Heterocyclic Chemistry" 20,645 (1983), the β-diketone of general formula V is derivatized with orthoacid amides (such as dimethylformamide dimethyl acetal) of general formula VIII Compounds are converted to enamine derivatives of general formula IX, which are then cyclized with hydroxylamine hydrochloride in the presence of a base such as sodium acetate in a solvent such as an alcohol (eg ethanol) to form compounds of general formula If.

也能够与WO96/21357和其中引用的文献类似地进行其中R13为COOR16，COR15，氰基，硝基或CONH2的通式I(Q＝Q6)的4-苯甲酰基异噁唑衍生物的制备。4-Benzoylisoxanes of the general formula I (Q=Q 6 ) wherein R 13 is COOR 16 , COR 15 , cyano, nitro or CONH 2 can also be carried out analogously to WO96/21357 and the literature cited therein. Preparation of azole derivatives.

通式Id的羧酸能够与已知方法类似地，例如根据下面的反应方案4和5所给方法制备。反应方案4路径a)：

Figure A9880674200381
路径b)：
Figure A9880674200391
反应方案5 Carboxylic acids of general formula Id can be prepared analogously to known methods, for example according to the methods given in Reaction Schemes 4 and 5 below. Reaction scheme 4 path a):
Figure A9880674200381
Path b):
Figure A9880674200391
Reaction scheme 5

其中R28为C1-C4烷基的通式XX的水杨酸衍生物根据反应方案4中的路径a)的链烯基化例如能够与标准的醚化方法类似地通过与其中Hal为卤素(例如氯、溴或碘)的通式XXV的烯丙基卤化物在非质子传递溶剂例如酰胺(例如N，N-二甲基甲酰胺(DMF)或1-甲基-2-吡咯烷酮(NMP))，亚砜(例如二甲基亚砜(DMSO))，酮(例如丙酮)或腈(例如乙腈)中，在碱，例如碳酸盐(例如碳酸钾或碳酸铯)或金属氢化物(例如氢化钠)存在下反应来进行。反应温度一般是0-110℃。The alkenylation of salicylic acid derivatives of the general formula XX in which R 28 is C 1 -C 4 alkyl according to route a) in Reaction Scheme 4 can for example be carried out analogously to the standard etherification method by Allyl halides of the general formula XXV of halogens (e.g. chlorine, bromine or iodine) are dissolved in aprotic solvents such as amides (e.g. N, N-dimethylformamide (DMF) or 1-methyl-2-pyrrolidone ( NMP)), sulfoxides (e.g. dimethyl sulfoxide (DMSO)), ketones (e.g. acetone) or nitriles (e.g. acetonitrile), in bases such as carbonates (e.g. potassium carbonate or cesium carbonate) or metal hydrides (such as sodium hydride) in the presence of the reaction to carry out. The reaction temperature is generally 0-110°C.

按反应方案4，通式XXI的烯丙基醚的随后Claisen重排例如能够在100℃-300℃下加热，任选在惰性溶剂例如芳族烃(例如二甲苯)中进行。此外，加热途径的Claisen重排例如也能够在没有溶剂的情况下在微波炉中进行。该Claisen重排例如描述在C.Ferri，“有机合成反应(Reaktionen der organischen Synthese)”，Georg ThiemeVerlag，Stuttgart，1978，461页及以后各页。According to Reaction Scheme 4, the subsequent Claisen rearrangement of allyl ethers of general formula XXI can be carried out, for example, with heating at 100° C. to 300° C., optionally in an inert solvent such as an aromatic hydrocarbon (eg xylene). Furthermore, thermally routed Claisen rearrangements, for example, can also be performed without solvents in a microwave oven. The Claisen rearrangement is described, for example, in C. Ferri, "Reactions in Organic Synthesis (Reaktionen der organischen Synthese)", Georg Thieme Verlag, Stuttgart, 1978, pages 461 ff.

根据反应方案4，所得到的通式XXII的苯酚衍生物然后例如用通式XXVI的硫代氨基甲酰卤(例如N，N-二甲基-硫代甲酰氯)在非质子传递溶剂例如酰胺(例如N，N-二甲基甲酰胺(DMF)或1-甲基-2-吡咯烷酮(NMP))，亚砜(例如二甲基亚砜(DMSO))，酮(例如丙酮)或腈(例如乙腈)中在碱例如碳酸盐(例如碳酸钾或碳酸铯)或金属氢化物(例如氢化钠)存在下加以酰化。酰化反应有利地在0-110℃之间的温度下进行。According to Reaction Scheme 4, the resulting phenol derivative of general formula XXII is then, for example, treated with a thiocarbamoyl halide of general formula XXVI (e.g. N,N-dimethyl-thioformyl chloride) in an aprotic solvent such as amide (such as N,N-dimethylformamide (DMF) or 1-methyl-2-pyrrolidone (NMP)), sulfoxides (such as dimethylsulfoxide (DMSO)), ketones (such as acetone) or nitriles ( eg acetonitrile) in the presence of a base such as a carbonate (eg potassium carbonate or cesium carbonate) or a metal hydride (eg sodium hydride). The acylation reaction is advantageously carried out at a temperature between 0-110°C.

在反应方案4中通式XXIII的硫代氨基甲酸酯的重排例如在惰性溶剂例如醚(例如二苯基醚)中通过在100-300℃之间的温度下加热进行并得到通式XXIV的硫醇氨基甲酸酯。该化合物然后使用碱或酸催化方法进行水解和环化而形成其中R2＝CH3和n＝0的通式Id的化合物。这可有利地用金属氢氧化物，例如氢氧化钠，或用无机酸，例如盐酸或硫酸在0℃-110℃之间的温度下进行。合适的溶剂例如是水，醚类例如四氢呋喃，卤代烃类例如二氯甲烷和芳族烃类例如甲苯。Rearrangement of thiocarbamates of general formula XXIII in reaction scheme 4 is carried out, for example, by heating at temperatures between 100-300° C. in an inert solvent such as an ether (eg diphenyl ether) and leads to general formula XXIV of thiol carbamates. This compound is then hydrolyzed and cyclized using base or acid catalyzed methods to form compounds of general formula Id where R2 = CH3 and n=0. This can advantageously be carried out with metal hydroxides, such as sodium hydroxide, or with mineral acids, such as hydrochloric acid or sulfuric acid, at temperatures between 0°C and 110°C. Suitable solvents are, for example, water, ethers such as tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.

所得其中R2为甲基和n为0的通式Id的苯并噻吩衍生物然后根据各种标准方法加以氧化。有利地，氧化例如在酸性溶剂例如有机酸(例如乙酸)中用过氧化氢或在惰性溶剂例如卤代烃(例如二氯甲烷)或芳族烃(例如甲苯)中用有机过酸如间-氯过苯甲酸(m-CPBA)来进行。氧化反应的温度一般是在0℃-110℃之间。在硫原子上的氧化程度(n＝1或2)能够由氧化剂的量来控制。The resulting benzothiophene derivatives of general formula Id wherein R2 is methyl and n is 0 are then oxidized according to various standard methods. Advantageously, oxidation, for example with hydrogen peroxide in an acidic solvent such as an organic acid (e.g. acetic acid) or with an organic peracid such as m- Chloroperbenzoic acid (m-CPBA) was used. The temperature of the oxidation reaction is generally between 0°C and 110°C. The degree of oxidation (n=1 or 2) on the sulfur atom can be controlled by the amount of oxidizing agent.

经历通式XXII的苯酚衍生物的酰化形成通式XXIII的硫代氨基甲酸酯，后一种化合物进行重排形成通式XXIV的硫醇氨基甲酸酯和然后水解和环化形成通式Id的化合物(n＝0)的以上反应序列例如能够与《有机合成》51，139(1971)类似地进行，而氧化形成通式Id的化合物(n＝1或2)的反应例如可按照H.O.House，“现代合成反应”W.A.Benjamin，Inc.，Menlo ParK，California，1972年，334-335页和353-354中所述进行。undergoes acylation of phenol derivatives of general formula XXII to form thiocarbamates of general formula XXIII, the latter compound undergoes rearrangement to form thiol carbamates of general formula XXIV and then hydrolyzes and cyclizes to form thiocarbamates of general formula The above reaction sequence of the compound (n=0) of Id, for example, can be carried out similarly to "Organic Synthesis" 51,139 (1971), and the reaction of the compound (n=1 or 2) of the general formula Id formed by oxidation, for example, can be carried out according to H.O. House, "Modern Synthetic Reactions" W.A. Benjamin, Inc., Menlo Park, California, 1972, pp. 334-335 and 353-354.

根据反应方案4的路径b)的亲电溴化例如与Chem.Communic.，1972年，214中类似地进行。通式XX的水杨酸衍生物的溴化能够在惰性溶剂例如卤代烃(例如二氯甲烷)中和在路易斯酸例如卤化钛(例如四氯化钛)存在下，在0-100℃的温度下进行。随后，所制备的通式XXb的溴代水杨酸衍生物与其中R29为C1-C4烷基的通式XXVb的三烷基锡-烯烃的偶联反应可与Angew.Chem.98，504(1986)中类似地在有机溶剂例如醚(例如四氢呋喃)，芳族烃(例如甲苯)中和在钯催化剂例如四(三苯基膦)钯存在下来进行。反应温度有利地为0-200℃。由路径b)获得的通式XXII的偶联产物例如能够按照与路径a)所述方法类似地被酰化，重排，水解和环化，和任选被氧化而形成通式Id的化合物。The electrophilic bromination according to route b) of reaction scheme 4 is carried out analogously, for example, in Chem. Communic., 1972, 214. Bromination of salicylic acid derivatives of general formula XX can be carried out in the presence of Lewis acids such as titanium halides (such as titanium tetrachloride) in an inert solvent such as halogenated hydrocarbons (such as dichloromethane) at 0-100 ° C temperature. Subsequently, the coupling reaction of the bromosalicylic acid derivative of the prepared general formula XXb with the trialkyltin-alkene of the general formula XXVb wherein R 29 is C 1 -C 4 alkyl can be compared with Angew.Chem.98 , 504 (1986) similarly in organic solvents such as ethers (eg tetrahydrofuran), aromatic hydrocarbons (eg toluene) and in the presence of palladium catalysts such as tetrakis(triphenylphosphine)palladium. The reaction temperature is advantageously from 0 to 200°C. Coupling products of general formula XXII obtained by route b) can, for example, be acylated, rearranged, hydrolyzed and cyclized, and optionally oxidized to form compounds of general formula Id analogously to those described for route a).

在反应方案5中其中R28为C1-C4烷基的通式XXa的邻溴代苯甲酸酯的芳族亲核取代反应能够与已知方法类似地进行，例如按照J.March“高等有机化学”第四版，John Wiley & Sons，New York，1992年，641-676页中所述那样。因此，通式XXa的苯甲酸酯与通式XXVa的链烯基硫化物在非质子传递溶剂例如酰胺(例如N，N-二甲基甲酰胺(DMF)或1-甲基-2-吡咯烷酮(NMP))，亚砜(例如二甲基亚砜(DMSO))，酮(例如丙酮)或腈(例如乙腈)中，在碱例如碳酸盐(例如碳酸钾或碳酸铯)或金属氢化物(例如氢化钠)存在下，在0-200℃的温度下进行反应。The aromatic nucleophilic substitution reaction of o-bromobenzoates of general formula XXa in which R 28 is C 1 -C 4 alkyl in reaction scheme 5 can be carried out analogously to known methods, for example according to J.March " As described in Advanced Organic Chemistry, Fourth Edition, John Wiley & Sons, New York, 1992, pp. 641-676. Therefore, the benzoic acid ester of general formula XXa and the alkenyl sulfide of general formula XXVa are in aprotic solvent such as amide (for example N,N-dimethylformamide (DMF) or 1-methyl-2-pyrrolidone (NMP)), sulfoxides (such as dimethylsulfoxide (DMSO)), ketones (such as acetone) or nitriles (such as acetonitrile), in bases such as carbonates (such as potassium carbonate or cesium carbonate) or metal hydrides The reaction is carried out at a temperature of 0-200° C. in the presence of (eg, sodium hydride).

在反应方案5中所制备的通式XXIa的硫代烯丙基醚的随后Claisen重排能够有利地按照《有机化学杂志》USSR 13，2437(1977)和关于通式XXI的烯丙基醚的反应方案4中所述方法类似地在100-300℃的温度下进行。通式XXIIa的苯硫酚的随后水解和环化和所得通式Id(n＝0)的二氢苯并[b]噻吩衍生物的选择性氧化同样有利地按照早已在反应方案4中描述的方法进行。The subsequent Claisen rearrangement of the thioallyl ethers of general formula XXIa prepared in Reaction Scheme 5 can be advantageously performed according to "Journal of Organic Chemistry" USSR 13,2437 (1977) and on allyl ethers of general formula XXI The process described in Reaction Scheme 4 is similarly carried out at a temperature of 100-300°C. The subsequent hydrolysis and cyclization of thiophenols of the general formula XXIIa and the selective oxidation of the resulting dihydrobenzo[b]thiophene derivatives of the general formula Id (n=0) are likewise advantageously carried out as already described in Reaction Scheme 4 method to proceed.

在反应方案1和2(路径a))中，其中X是离去基团例如卤素(例如溴，碘或尤其氯)的通式III和I的活化羧酸衍生物能够根据已知的标准方法来制备，按照例如由C.Ferri在“有机合成反应”，Georg ThiemeVerlag，Stuttgart，1978年，461页及以下各页中所述方法，例如根据下面的反应方案6。In reaction schemes 1 and 2 (pathway a)), the activated carboxylic acid derivatives of general formula III and I, wherein X is a leaving group such as a halogen (e.g. bromine, iodine or especially chlorine) can be synthesized according to known standard methods. To prepare, according to the method described for example by C. Ferri in "organic synthesis reaction", Georg ThiemeVerlag, Stuttgart, 1978, pp. 461 et seq., for example according to the following reaction scheme 6.

反应方案6：

Figure A9880674200421
Reaction scheme 6:
Figure A9880674200421

根据反应方案6，通式III(X＝离去基团)和I(X＝卤素)的化合物的制备例如有利地通过使用卤化剂例如亚硫酰卤(例如亚硫酰氯或溴)，卤化磷或三卤氧化磷(例如五氯化磷或三氯氧化磷，或五溴化磷或磷酰溴)，或草酰卤(例如草酰氯)，或通过使用一种用于形成活化酯类的试剂(例如通式X的N，N′-二环己基碳化二亚胺(DCC)或N-乙基-N′-(3-二甲基氨基丙基)碳化二亚胺(EDC))来进行。当通式X的化合物是卤化剂时，基团X例如是离去基团，例如卤素(例如氟，溴，碘或尤其氯)，和W1是例如PCl2，SOCl，SOBr或ClCOCO。According to Reaction Scheme 6, compounds of general formula III (X=leaving group) and I (X=halogen) are prepared, for example, advantageously by using halogenating agents such as thionyl halides (for example thionyl chloride or bromine), phosphorus halides or phosphorus oxyhalides (such as phosphorus pentachloride or phosphorus oxychloride, or phosphorus pentabromide or phosphorus oxybromide), or oxalyl halides (such as oxalyl chloride), or by using a Reagents (such as N,N'-dicyclohexylcarbodiimide (DCC) or N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) of the general formula X) to conduct. When the compound of general formula X is a halogenating agent, the group X is for example a leaving group such as halogen (eg fluorine, bromine, iodine or especially chlorine), and W 1 is eg PCl 2 , SOCl, SOBr or ClCOCO.

该操作任选是在惰性有机溶剂中，例如在脂族，卤代脂族，芳族或卤代芳族烃，例如正己烷，苯，甲苯，二甲苯，二氯甲烷，1，2-二氯乙烷或氯苯中，在-20℃至反应混合物的回流温度之间，优选在40-150℃之间的反应温度下，和在催化量的N，N-二甲基甲酰胺存在下进行。该反应是已知的且就离去基团X而言的其各种变化形式在文献中有描述。The operation is optionally in an inert organic solvent, such as an aliphatic, haloaliphatic, aromatic or halogenated aromatic hydrocarbon, such as n-hexane, benzene, toluene, xylene, dichloromethane, 1,2-bis In ethyl chloride or chlorobenzene, at a reaction temperature between -20°C and the reflux temperature of the reaction mixture, preferably between 40-150°C, and in the presence of a catalytic amount of N,N-dimethylformamide conduct. This reaction is known and various variations thereof with respect to the leaving group X are described in the literature.

通式V，VII和IX(反应方案3)的化合物是新颖的。它们是合成通式If的化合物的重要中间体。所以，本发明也涉及这些化合物。Compounds of general formula V, VII and IX (Scheme 3) are novel. They are important intermediates for the synthesis of compounds of general formula If. Therefore, the present invention also relates to these compounds.

其中Z1＝C(R6)R7，Z2＝(W)n6，Z3＝C(R6)R7和n4＝O的通式IV化合物(反应方案1)是已知的并能够按照例如US-A-5 006 150，WO97/08164，DE-OS-3 818 958和DE-OS-3 902 818中所述的方法类似制备。Compounds of the general formula IV (Scheme 1) in which Z 1 =C(R 6 )R 7 , Z 2 =(W) n6 , Z 3 =C(R 6 )R 7 and n 4 =0 are known and It can be prepared analogously as described, for example, in US-A-5 006 150 , WO 97/08164 , DE-OS-3 818 958 and DE-OS-3 902 818 .

其中Z1＝CH，Z2＝O，S或-(CH2)n5-，Z3＝CH和n4＝2的通式IV化合物(反应方案1)是已知的并能够按照与EP-A-0 338 992中描述的方法类似制备。Compounds of general formula IV (Scheme 1) in which Z 1 =CH, Z 2 =O, S or -(CH 2 ) n5 -, Z 3 =CH and n 4 =2 are known and can be used in accordance with EP- Prepared analogously to the method described in A-0 338 992.

其中Z1＝CH2，Z2＝CHNHR9，Z3＝CH2和n4＝0的通式IV化合物(反应方案1)是已知的并能够按照与EP-A-0 278 907中描述的方法类似制备。Compounds of the general formula IV (Scheme 1) in which Z 1 =CH 2 , Z 2 =CHNHR 9 , Z 3 =CH 2 and n 4 =0 are known and can be obtained as described in EP-A-0 278 907 The method is similar to the preparation.

其中Z1＝NR10，Z2＝O，Z3＝C(R6)R7和n4＝0的通式IV化合物(反应方案1)是已知的并能够按照与WO96/26192和US-A-5 336 662中描述的方法类似制备。Compounds of the general formula IV (Scheme 1) wherein Z 1 =NR 10 , Z 2 =O, Z 3 =C(R 6 )R 7 and n 4 =0 are known and can be obtained according to WO96/26192 and US - Prepared analogously to the method described in A-5 336 662.

其中R11和R12如通式I中所定义的通式IVa化合物(反应方案2)是已知的并能够按照与WO96/26206和WO97/08164中描述的方法类似制备。Compounds of general formula IVa in which R11 and R12 are as defined in general formula I (Scheme 2) are known and can be prepared analogously to the methods described in WO96/26206 and WO97/08164.

在反应方案3中的通式V的化合物能够根据标准方法，例如从通式XXVII的对应酯获得：

Figure A9880674200431
其中R1-R5和n如通式I中所定义和R28是C1-C4烷基，例如经过Claisen缩合，或通过与通式XXVIII的酮基羧酸盐反应而从通式III的化合物获得：
Figure A9880674200432
其中R14如通式I中所定义和M+是碱金属离子(例如参见WO96/26192，EP-A-0 496 631)。Compounds of general formula V in Reaction Scheme 3 can be obtained according to standard methods, e.g. from the corresponding esters of general formula XXVII:
Figure A9880674200431
wherein R 1 -R 5 and n are as defined in general formula I and R 28 is C 1 -C 4 alkyl, e.g. via Claisen condensation, or from general formula III by reaction with a ketocarboxylate of general formula XXVIII The compound obtains:
Figure A9880674200432
wherein R 14 is as defined in general formula I and M + is an alkali metal ion (see eg WO96/26192, EP-A-0 496 631).

通式XX(反应方案4)的水杨酸衍生物是已知的(其中一些是可商购的，例如当R5是氨基(4-氨基水杨酸))或能够容易地由标准方法制备，例如从4-氨基水杨酸开始经过重氮化反应，Sandmeyer反应和芳族亲核取代反应(例如参见J.March，“高等有机化学”，第4版，John Wiley& Sons，New Yoork，1992，641-676页)或所制备卤化物的Heck反应。Salicylic acid derivatives of general formula XX (Scheme 4) are known (some of which are commercially available, for example when R is amino( 4 -aminosalicylic acid)) or can be easily prepared by standard methods , for example starting from 4-aminosalicylic acid via diazotisation, Sandmeyer and aromatic nucleophilic substitution reactions (see for example J. March, "Advanced Organic Chemistry", 4th edition, John Wiley & Sons, New Yoork, 1992 , pp. 641-676) or the Heck reaction of the prepared halides.

通式XXa的苯甲酸衍生物(反应方案5)是已知的或能够容易地通过溴化对应的苯甲酸衍生物而获得(参见反应方案4，路径b))。Benzoic acid derivatives of general formula XXa (reaction scheme 5) are known or can be easily obtained by bromination of the corresponding benzoic acid derivatives (see reaction scheme 4, route b)).

在反应方案3-6中使用的通式VI、VIII、X、XXV、XXVa、XXVb和XXVI的试剂是已知的或能够与所公开方法类似地制备。The reagents of general formula VI, VIII, X, XXV, XXVa, XXVb and XXVI used in Reaction Schemes 3-6 are known or can be prepared analogously to the disclosed methods.

为了制备依据R1和R2的定义(二氢苯并[b]噻吩的2-位)来官能化的所有通式I的其它化合物，大量已知的标准方法是可行的，例如烷基化，卤化，酰化，酰胺化，肟化，氧化和还原，合适制备方法的选择受到各中间体中取代基的性能(反应活性)的主宰。For the preparation of all other compounds of the general formula I which are functionalized according to the definition of R and R ( 2 -position of dihydrobenzo[b]thiophene), a number of known standard methods are possible, such as alkylation , halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of a suitable preparation method is governed by the properties (reactivity) of the substituents in the respective intermediates.

为了制备其中Q为基团Q1-Q4的依据R8的定义被官能化的所有通式I的其它化合物，大量已知的标准方法是可行的，例如烷基化，酰化和用硫试剂(例如P2S5或Lawesson)处理，合适制备方法的选择受到各中间体中取代基的性能(反应活性)的主宰(参见WO97/08164和DE-OS-3 902 818)。For the preparation of all other compounds of the general formula I in which Q is a radical Q 1 -Q 4 which is functionalized according to the definition of R 8 , a large number of known standard methods are possible, such as alkylation, acylation and reaction with sulfur Treatment with reagents (eg P 2 S 5 or Lawesson), the choice of a suitable preparation method is governed by the properties (reactivity) of the substituents in the respective intermediates (see WO 97/08164 and DE-OS-3 902 818).

在通式I的范围内所有的其它化合物(考虑二氢苯并[b]噻吩的化学性能或与二氢苯并[b]噻吩的结构有关的Q部分或Q环)能够容易地按照与制备实施例P1-P11中所述方法类似的方式，或例如与所给出专利说明书中描述的方法类似的方法制备。All other compounds within the scope of general formula I (considering the chemical properties of dihydrobenzo [b] thiophene or the Q moiety or Q ring related to the structure of dihydrobenzo [b] thiophene) can be easily prepared according to the Prepared in an analogous manner to the methods described in Examples P1-P11, or eg to the methods described in the given patent specification.

通式I的最终产物能够按常规方式通过浓缩或蒸发溶剂来分离，并通过固体残余物在不易溶解它们的溶剂(例如醚，芳族烃或氯代烃)中的重结晶或研制，或蒸馏或借助于柱色谱和合适的洗脱剂加以提纯。反应序列(其中有利的是进行某些反应以避免可能发生的二级反应)对于本技术领域中普通技术人员是十分熟悉的。除非该合成尤其体现在纯异构体的分离上，否则产物能够以两种或多种异构体的混合物形式获得。异构体能够根据本身已知的方法分离。The final products of general formula I can be isolated in a conventional manner by concentration or evaporation of the solvent, and by recrystallization or trituration of the solid residue in solvents which do not readily dissolve them (e.g. ethers, aromatic or chlorinated hydrocarbons), or distillation Or purify by means of column chromatography and a suitable eluent. Reaction sequences, in which it is advantageous to perform certain reactions to avoid possible secondary reactions, are well known to those of ordinary skill in the art. Unless the synthesis involves in particular the isolation of pure isomers, products can be obtained as mixtures of two or more isomers. Isomers can be separated according to methods known per se.

对于通式I化合物的根据本发明的用途，或包括这些化合物的组合物的用途，必须考虑农业中常见的所有施用方法，例如出芽前施用，出芽后施用和拌种，以及各种方法和技术，如活性成分的受控释放。为了该目的，活性成分的溶液被施加在矿物粒状载体上或聚合物粒料(脲/甲醛树脂)上和然后加以干燥。如果需要，还有可能涂敷一涂层(包衣粒料)，这使得活性成分在特定时间内以预计的量释放出来。For the use according to the invention of the compounds of the general formula I, or the use of compositions comprising these compounds, all application methods customary in agriculture, such as pre-emergence application, post-emergence application and seed dressing, as well as various methods and techniques must be considered , such as the controlled release of active ingredients. For this purpose, a solution of the active ingredient is applied to a mineral granular carrier or to polymer pellets (urea/formaldehyde resin) and then dried. If desired, it is also possible to apply a coating (coated granules), which allows the active ingredient to be released in a predetermined amount within a specific time.

通式I的化合物能够以未改性形式使用，也就是说在合成后原样使用，但它们优选按常规方式与配方技术中常常使用的助剂一起被配制成例如可乳化的浓缩物，直接可喷雾的或可稀释的溶液剂，稀乳液，可湿性粉剂，可溶性粉剂，粉剂，粒剂或微胶囊剂。这类配制剂例如描述在WO97/34485的第9-13页。与组合物的性质一样，施用方法如喷雾、雾化、粉化、润滑、撒播或浇泼可根据预定的目的和现场环境来选择。The compounds of the general formula I can be used in unmodified form, that is to say as synthesized, but they are preferably formulated in a customary manner together with the auxiliaries usually used in formulation technology, for example as emulsifiable concentrates, directly available Sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, powders, granules or microcapsules. Such formulations are described, for example, on pages 9-13 of WO 97/34485. Like the nature of the composition, the method of application such as spraying, atomizing, pulverizing, lubricating, broadcasting or pouring can be selected according to the intended purpose and site conditions.

配制剂，也就是说包括通式I的化合物(活性成分)或至少一种通式I的化合物和通常一种或多种固体或液体配方助剂的组合物、制剂或混合物是按已知方式制备，例如，通过将活性成分与配方助剂例如溶剂或固体载体一起均匀混合和/或研磨。表面活性化合物(表面活性剂)也可另外用于配制剂的制备中。溶剂和固体载体的实例，例如，在WO97/34485的第6页中给出。Formulations, that is to say compositions, preparations or mixtures comprising a compound of the general formula I (active ingredient) or at least one compound of the general formula I and usually one or more solid or liquid formulation auxiliaries are prepared in a known manner Preparation, for example, by uniformly mixing and/or grinding the active ingredient with formulation auxiliaries such as solvents or solid carriers. Surface-active compounds (surfactants) can additionally also be used in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, on page 6 of WO97/34485.

取决于待配制的通式I化合物的性质，合适的表面活性化合物是具有良好乳化、分散和润湿性能的非离子、阳离子和/或阴离子表面活性剂和表面活性剂混合物。合适的阴离子、非离子和阳离子表面活性剂的例子例如列于WO97/34485的第7和8页中。Depending on the nature of the compounds of the general formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, on pages 7 and 8 of WO97/34485.

另外，在配方技术中常用的表面活性剂，它们尤其被描述在“McCutcheon′s Detergents and Emulsifier Annual”MC出版公司，Ridgewoood New Jersey，1981年，Stache，H.，“Tensid-Taschenbuch”，Carl Hanser Verlag，Munich/Vienna 1981，以及M.和J.Ash，“表面活性剂大全”，I-III卷，Chemical Publishing Co.，New York，1980-81，也适合制备本发明的组合物。In addition, commonly used surfactants in formulation technology, they are described inter alia in "McCutcheon's Detergents and Emulsifier Annual" MC Publishing Company, Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Munich/Vienna 1981, and M. and J. Ash, "Encyclopedia of Surfactants", Volumes I-III, Chemical Publishing Co., New York, 1980-81, are also suitable for preparing the compositions of the invention.

除草组合物一般含有0.1-99wt％，尤其0.1-95wt％的除草剂，1-99.9wt％，尤其5-99.8wt％的固体或液体配方助剂，以及0-25wt％，尤其0.1-25wt％的表面活性剂。尽管商购产品优选被配制为浓缩物，最终的用户一般使用稀释的配制剂。组合物也可包括其它成分，如稳定剂，例如植物油或环氧化植物油(环氧化椰子油，菜籽油或大豆油)，消泡剂(例如硅油)，防腐剂，粘度调节剂，粘结剂，增粘剂，和肥料或其它活性成分。The herbicidal composition generally contains 0.1-99wt%, especially 0.1-95wt% of herbicide, 1-99.9wt%, especially 5-99.8wt% of solid or liquid formulation auxiliaries, and 0-25wt%, especially 0.1-25wt% of surfactants. While commercially available products are preferably formulated as concentrates, end users typically use dilute formulations. The composition may also include other ingredients such as stabilizers, such as vegetable oils or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents (such as silicone oils), preservatives, viscosity regulators, viscosity Binders, tackifiers, and fertilizers or other active ingredients.

通式I的化合物能够成功地以异构体形式I1-I4和Ic(Q是基团Q1-Q4和R8是OH)或I6，I7和Ie(Q是基团Q5)的混合物形式或以纯异构体形式I1-I4或Ic，或I6，I7或Ie的形式使用，一般使用在植物或其生长场所上，施用率是0.001-4kg/ha，尤其0.005-2kg/ha。需要达到所需效果的浓度能够由实验测定。取决于该作用的性质，栽培植物和杂草的发展阶段，和取决于应用(地方，时间，方法)并能够作为这些参数的函数在宽的范围内变化。Compounds of general formula I can be successfully obtained in the isomeric forms I 1 -I 4 and Ic (Q is a group Q 1 -Q 4 and R 8 is OH) or I 6 , I 7 and Ie (Q is a group Q 5 ) in the form of mixtures or in the form of pure isomers I 1 -I 4 or Ic, or I 6 , I 7 or Ie, generally used on plants or their growth sites, the application rate is 0.001-4kg/ha, Especially 0.005-2kg/ha. The concentration needed to achieve the desired effect can be determined experimentally. Depending on the nature of the action, the stage of development of the cultivated plants and weeds, and on the application (place, time, method) and can vary within wide ranges as a function of these parameters.

通式I的化合物突出表现在除草和生长抑制性能，使它们用于有用植物的作物，尤其是禾谷类，棉花，大豆，甘蔗，糖用甜菜，种植作物，油菜，玉米和稻谷，和用于非选择性杂草控制。术语“作物”被理解为包括：由于普通的育种方法或基因技术已经能够耐受除草剂或一类除草剂的作物。待控制的杂草可以是单子叶或双子叶杂草，例如，繁缕属(Stellaria)，水田芥属(Nasturtium)，翦股颖属(Agrostis)，马唐属(Digitaria)，燕麦属(Avena)，狗尾草属(Setaria)，芥属(Sinapis)，毒麦属(Lolium)，茄属(Solanum)，菜豆属(Phaseolus)，稗属(Echinochloa)，莞草属(Scirpus)，雨久花属(Monochoria)，慈菇属(Sagittaria)，雀麦属(Bromus)，看麦娘属(Alopecurus)，阿拉伯高粱(Sorghum halepense)，筒轴茅属(Rottboellia)，莎草属(Cyperus)，苘麻属(Abutilon)，黄花稔属(Sida)，苍耳属(Xanthium)，苋属(Amaranthus)，藜属(Chenopodium)，甘薯属(Ipomoea)，菊属(Chrysanthemum)，猪殃殃属(Galium)，堇菜属(Viola)和婆婆纳属(Veronica)。The compounds of the general formula I are distinguished by their herbicidal and growth-inhibiting properties, making them useful for crops of useful plants, especially cereals, cotton, soybean, sugar cane, sugar beet, plantation crops, rapeseed, maize and rice, and for Non-selective weed control. The term "crops" is understood to include crops which have been made tolerant to a herbicide or a class of herbicides as a result of common breeding methods or genetic technology. The weeds to be controlled may be monocotyledonous or dicotyledonous, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena ), Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Yujiuhua (Monochoria), Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium , Viola and Veronica.

下面的实施例进一步说明本发明但不限定本发明的范围。The following examples further illustrate the invention but do not limit the scope of the invention.

制备实施例：Preparation Examples:

实施例P1：2-烯丙氧基-4-氯苯甲酸甲酯 Example P1: Methyl 2-allyloxy-4-chlorobenzoate

在搅拌下将50g(0.36mol)的碳酸钾加入到56g(0.3mol)的4-氯水杨酸甲酯在200ml二甲基亚砜中的溶液中。当轻微的放热反应平息下来后，在25℃下滴加40g(0.33mol)的烯丙基溴。反应混合物在22℃下搅拌16小时，倾倒在水中和通过用乙醚振荡进行萃取。合并的醚相用水洗涤，用硫酸钠干燥和通过蒸发进行浓缩。残余物从少量己烷中重结晶。获得了62g(理论值的91.2％)熔点为61-62℃的所需产物。50 g (0.36 mol) of potassium carbonate were added to a solution of 56 g (0.3 mol) of methyl 4-chlorosalicylate in 200 ml of dimethylsulfoxide with stirring. After the slightly exothermic reaction had subsided, 40 g (0.33 mol) of allyl bromide was added dropwise at 25°C. The reaction mixture was stirred at 22°C for 16 hours, poured into water and extracted by shaking with diethyl ether. The combined ether phases are washed with water, dried over sodium sulfate and concentrated by evaporation. The residue was recrystallized from a small amount of hexane. 62 g (91.2% of theory) of the desired product with a melting point of 61-62° C. are obtained.

实施例P2：2-羟基-3-(3-丙烯基)-4-氯苯甲酸甲酯 Example P2: Methyl 2-hydroxy-3-(3-propenyl)-4-chlorobenzoate

在圆底烧瓶中熔解97.9g(0.432mol)的2-烯丙氧基-4-氯苯甲酸甲酯(实施例P1)并在500瓦的微波炉中辐射5分钟。发生放热反应。反应混合物被冷却，得到97.1g(理论值的99.1％)熔点为32-35℃的所需产物。97.9 g (0.432 mol) of methyl 2-allyloxy-4-chlorobenzoate (Example P1 ) were melted in a round bottom flask and irradiated in a microwave at 500 watts for 5 minutes. An exothermic reaction occurred. The reaction mixture was cooled, yielding 97.1 g (99.1% of theory) of the desired product with a melting point of 32-35°C.

实施例P3：2-氧基-(N，N-二甲基-硫代氨基甲酰基)-3-(3-丙烯基)-4-苯甲酸甲酯

Figure A9880674200473
Example P3: 2-Oxy-(N,N-dimethyl-thiocarbamoyl)-3-(3-propenyl)-4-benzoic acid methyl ester
Figure A9880674200473

97g(0.428mol)的2-羟基-3-(3-丙烯基)-4-氯苯甲酸甲酯(实施例P2)和69g(0.5mol)的碳酸钾搅拌在400ml二甲基甲酰胺中达1/2小时。然后向其中滴加55.6g(0.45mol)的N，N-二甲基硫代氨基甲酰氯在200ml二甲基甲酰胺中的溶液。反应混合物在22℃下搅拌22小时。为了完成反应，添加11g(0.09mol)的N，N-二甲基-硫代氨基甲酰氯和15g(0.11mol)碳酸钾。在22℃下保持另外24小时后，，反应混合物被倾入冰水混合物中，通过用乙酸乙酯振荡进行萃取。乙酸乙酯相用水洗涤，然后用盐水洗涤，用硫酸钠干燥和蒸发浓缩。残余物在硅胶上进行柱色谱分离(洗脱液：乙酸乙酯/己烷1/3)，得到114.5g(理论值的85％)油形式的所需产物。97g (0.428mol) of 2-hydroxyl-3-(3-propenyl)-4-chlorobenzoic acid methyl ester (embodiment P2) and the potassium carbonate of 69g (0.5mol) are stirred in 400ml dimethylformamide to reach 1/2 hour. A solution of 55.6 g (0.45 mol) of N,N-dimethylthiocarbamoyl chloride in 200 ml of dimethylformamide was then added dropwise thereto. The reaction mixture was stirred at 22°C for 22 hours. To complete the reaction, 11 g (0.09 mol) of N,N-dimethyl-thiocarbamoyl chloride and 15 g (0.11 mol) of potassium carbonate were added. After a further 24 hours at 22°C, the reaction mixture was poured into a mixture of ice and water and extracted by shaking with ethyl acetate. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and concentrated by evaporation. The residue is subjected to column chromatography on silica gel (eluent: ethyl acetate/hexane 1/3) to give 114.5 g (85% of theory) of the desired product in the form of an oil.

实施例P4：2-巯基-(N，N-二甲基-氨基甲酰基)-3-(3-丙烯基)-4-氯苯甲酸甲酯

Figure A9880674200481
Example P4: Methyl 2-mercapto-(N,N-dimethyl-carbamoyl)-3-(3-propenyl)-4-chlorobenzoate
Figure A9880674200481

经5小时在205-210℃下向100ml二苯基醚中滴加已溶于150ml二苯基醚中的114.5(0.365mol)的2-氧基-(N，N-二甲基-硫代氨基甲酰基)-3-(3-丙烯基)-4-苯甲酸甲酯(实施例P3)。温度在205℃下保持另外1.5小时。在冷却之后，二苯基醚在0.04毫巴的压力下被蒸馏出来。残余物在硅胶上进行柱色谱分离(洗脱液：乙酸乙酯/己烷1/1)，得到90.2g(理论值的78.8％)油形式的所需产物。Add dropwise 114.5 (0.365 mol) of 2-oxyl-(N,N-dimethyl-thio Carbamoyl)-3-(3-propenyl)-4-benzoic acid methyl ester (Example P3). The temperature was maintained at 205°C for an additional 1.5 hours. After cooling, the diphenyl ether was distilled off at a pressure of 0.04 mbar. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/hexane 1/1), which gave 90.2 g (78.8% of theory) of the desired product in the form of an oil.

实施例P5：4-氯-2-甲基-2，3-二氢-苯并[b]噻吩-7-羧酸

Figure A9880674200482
Example P5: 4-Chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid
Figure A9880674200482

将90.2g(0.287mol)的2-巯基-(N，N-二甲基-氨基甲酰基)-3-(3-丙烯基)-4-氯苯甲酸甲酯(实施例P4)在150ml乙酸和200ml浓盐酸中加热回流20小时。反应混合物在旋转蒸发器中浓缩，残余物与水一起搅拌和冷却。固体物质被过滤出来，在60℃下真空干燥，得到66g(理论值的100％)熔点为215-218℃的所需产物。90.2g (0.287mol) of 2-mercapto-(N,N-dimethyl-carbamoyl)-3-(3-propenyl)-4-chlorobenzoic acid methyl ester (embodiment P4) in 150ml acetic acid and 200ml of concentrated hydrochloric acid and heated to reflux for 20 hours. The reaction mixture was concentrated in a rotary evaporator, the residue was stirred with water and cooled. The solid material was filtered off and dried in vacuo at 60°C, yielding 66 g (100% of theory) of the desired product with a melting point of 215-218°C.

实施例P6：4-氯-2-甲基-1，1-二氧代-2，3-二氢-苯并[b]噻吩-7-羧酸 Example P6: 4-Chloro-2-methyl-1,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid

将20g(0.0875mol)的4-氯-2-甲基-2，3-二氢-苯并[b]噻吩-7-羧酸(实施例P5)悬浮于150ml乙酸中并加热至70℃。然后滴加24ml大约35％的过氧化氢。反应是放热的。在80℃下，移走加热浴，以一种使温度保持在80℃下的方式连续滴加。反应混合物然后在70-75℃下保持1小时。反应混合物然后使用旋转蒸发器进行浓缩，直至沉积晶体。添加水；混合物被冷却和过滤出沉淀的晶体。在60℃下真空干燥，获得17g(理论值的74％)熔点为223-225℃的所需产物。20 g (0.0875 mol) of 4-chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P5) were suspended in 150 ml acetic acid and heated to 70°C. Then 24ml of approximately 35% hydrogen peroxide was added dropwise. The reaction is exothermic. At 80°C, the heating bath was removed and the addition continued dropwise in such a way that the temperature was maintained at 80°C. The reaction mixture was then maintained at 70-75°C for 1 hour. The reaction mixture was then concentrated using a rotary evaporator until crystals were deposited. Water was added; the mixture was cooled and the precipitated crystals were filtered off. Drying in vacuo at 60° C. gives 17 g (74% of theory) of the desired product with a melting point of 223-225° C.

实施例P7：4-氯-2-甲基-1，1-二氧代-2，3-二氢-苯并[b]噻吩-7-羧酰氯 Example P7: 4-Chloro-2-methyl-1,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride

将16.7g(0.06mol)的4-氯-2-甲基-1，1-二氧代-2，3-二氢-苯并[b]噻吩-7-羧酸(实施例P6)在100ml甲苯中加热至90℃。滴加3滴二甲基甲酰胺，然后经20分钟滴加9.5g(0.08mol)的亚硫酰氯，获得透明的溶液。反应混合物在100℃下加热3小时，然后通过使用旋转蒸发器进行蒸发来浓缩，得到17g固体物质形式的所需产物。16.7g (0.06mol) of 4-chloro-2-methyl-1,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P6) in 100ml Heated to 90°C in toluene. 3 drops of dimethylformamide and then 9.5 g (0.08 mol) of thionyl chloride were added dropwise over 20 minutes to obtain a clear solution. The reaction mixture was heated at 100°C for 3 hours and then concentrated by evaporation using a rotary evaporator to afford 17 g of the desired product as a solid material.

实施例P8：(2，3-二氢-4-氯-2-甲基苯并[b]噻吩-7-基)(2-羟基-6-氧代-1-环己烯-1-基)甲酮S，S-二氧化物 Example P8: (2,3-dihydro-4-chloro-2-methylbenzo[b]thiophen-7-yl)(2-hydroxy-6-oxo-1-cyclohexen-1-yl ) Methanone S, S-dioxide

在5℃下将9.5g(0.094mol)三乙胺加入到3.6g(0.0314mol)的1，3-环己烷二酮在80ml二氯甲烷中的溶液中。在5℃下，滴加8.8g(0.0314mol)的4-氯-2-甲基-1，1-二氧代-2，3-二氢-苯并[b]噻吩-7-羧酰氯(实施例P7)在20ml二氯甲烷中的溶液。在22℃下1小时后，添加0.5ml的丙酮合氰化氢。在5.5小时后，反应混合物通过用2N盐酸振荡进行萃取。分离出二氯甲烷相，用硫酸钠干燥，蒸发浓缩，然后将残余物溶解在少量温热的丙酮中。在静置过程中产物结晶出来。在过滤后，获得5.5g(理论值的50％)熔点为170-172℃的所需产物。9.5 g (0.094 mol) of triethylamine were added to a solution of 3.6 g (0.0314 mol) of 1,3-cyclohexanedione in 80 ml of dichloromethane at 5°C. At 5° C., 8.8 g (0.0314 mol) of 4-chloro-2-methyl-1,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride ( Example P7) Solution in 20 ml of dichloromethane. After 1 hour at 22° C., 0.5 ml of acetone cyanohydrin was added. After 5.5 hours, the reaction mixture was extracted by shaking with 2N hydrochloric acid. The dichloromethane phase is separated off, dried over sodium sulfate, concentrated by evaporation and the residue is dissolved in a little warm acetone. The product crystallized out during standing. After filtration, 5.5 g (50% of theory) of the desired product with a melting point of 170-172° C. are obtained.

实施例9：4-氯-2-甲基-2，3-二氢-苯并[b]噻吩-7-羧酰氯 Example 9: 4-Chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride

将45.7g(0.2mol)4-氯-2-甲基-2，3-二氢-苯并[b]噻吩-7-羧酸(实施例P5)、23.8g(0.22mol)亚硫酰氯和几滴二甲基甲酰胺在300ml甲苯中于100℃下加热18小时。蒸发浓缩得到所需产物，其无需提纯而进一步使用。45.7 g (0.2 mol) of 4-chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P5), 23.8 g (0.22 mol) of thionyl chloride and A few drops of dimethylformamide were heated in 300 ml of toluene at 100°C for 18 hours. Concentration by evaporation gave the desired product which was used further without purification.

实施例10：(2，3-二氢-4-氯-2-甲基苯并[b]噻吩-7-基)(1，3-二甲基-5-羟基-1H-吡唑-4-基)甲酮 Example 10: (2,3-Dihydro-4-chloro-2-methylbenzo[b]thiophen-7-yl)(1,3-Dimethyl-5-hydroxy-1H-pyrazole-4 -yl)methanone

将2.3g(0.02mol)1，3-二甲基吡唑啉酮-5和2.2g(0.022mol)三乙胺悬浮于80ml乙酸乙酯中并冷却至5℃，然后加入50g(0.02mol)4-氯-2-甲基-2，3-二氢-苯并[b]噻吩-7-羧酰氯(实施例P9)在20ml乙酸乙酯中的溶液。反应混合物于22℃搅拌18小时，滤出盐并使用旋转蒸发器进行蒸发浓缩。将残余物溶于70ml二甲基甲酰胺中并加入2.2g(0.022mol)三乙胺和0.2g氰化钾。于22℃将反应混合物静置18小时并蒸发二甲基甲酰胺。将乙酸乙酯和5ml冰乙酸加入残余物中并通过用水振荡而萃取所得溶液。分离有机相，用硫酸钠干燥并蒸发浓缩。用乙醚研制得到熔点为191-193℃的所需产物。Suspend 2.3g (0.02mol) of 1,3-dimethylpyrazolone-5 and 2.2g (0.022mol) of triethylamine in 80ml of ethyl acetate and cool to 5°C, then add 50g (0.02mol) Solution of 4-chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride (Example P9) in 20 ml ethyl acetate. The reaction mixture was stirred at 22° C. for 18 hours, the salt was filtered off and concentrated by evaporation using a rotary evaporator. The residue was dissolved in 70 ml of dimethylformamide and 2.2 g (0.022 mol) of triethylamine and 0.2 g of potassium cyanide were added. The reaction mixture was allowed to stand at 22°C for 18 hours and dimethylformamide was evaporated. Ethyl acetate and 5 ml of glacial acetic acid were added to the residue and the resulting solution was extracted by shaking with water. The organic phase is separated off, dried over sodium sulfate and concentrated by evaporation. Trituration with ether gave the desired product, mp 191-193°C.

实施例P11：(2，3-二氢-4-氯-2-甲基苯并[b]噻吩-7-基)(1，3-二甲基-5-羟基-1H-吡唑-4-基)甲酮S，S-二氧化物 Example P11: (2,3-Dihydro-4-chloro-2-methylbenzo[b]thiophen-7-yl)(1,3-Dimethyl-5-hydroxy-1H-pyrazole-4 -yl)methanone S,S-dioxide

将已溶于30ml二氯甲烷中的2.0g(0.0115mol)的3-氯过苯甲酸加入到已溶于40ml二氯甲烷中的1.7g(0.0052mol)的(2，3-二氢-4-氯-2-甲基苯并[b]噻吩-7-基)(1，3-二甲基-5-羟基-1H-吡唑-4-基)甲酮(实施例P10)中。反应混合物在22℃下静置2天，然后用饱和的碳酸氢钠水溶液振荡进行萃取。碳酸氢盐相用浓盐酸酸化，过滤出所形成的沉淀物。如此获得的固体物质用乙醚研制，通过过滤加以分离，得到1.6g熔点为230-233℃的所需产物。2.0g (0.0115mol) of 3-chloroperbenzoic acid dissolved in 30ml of dichloromethane was added to 1.7g (0.0052mol) of (2,3-dihydro-4 -Chloro-2-methylbenzo[b]thiophen-7-yl)(1,3-dimethyl-5-hydroxy-1H-pyrazol-4-yl)methanone (Example P10). The reaction mixture was left standing at 22°C for 2 days, and then extracted with saturated aqueous sodium bicarbonate solution by shaking. The bicarbonate phase was acidified with concentrated hydrochloric acid and the precipitate formed was filtered off. The solid material thus obtained was triturated with ether and isolated by filtration to give 1.6 g of the desired product, mp 230-233°C.

按照类似方式并根据反应方案1-5中和本文中引用的参考文献所述的那些方法，也有可能制备出在下表中列出的优选化合物。In a similar manner and according to those described in Reaction Schemes 1-5 and in the references cited therein, it is also possible to prepare the preferred compounds listed in the table below.

表1：优选的一组通式I化合物对应于通式Id

Figure A9880674200512
其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Id的特定化合物。Table 1: A preferred group of compounds of general formula I corresponding to general formula Id
Figure A9880674200512
Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of the general formula Id are thus disclosed.

表2：优选的另一组通式I化合物对应于通式Ig

Figure A9880674200521
其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Ig的特定化合物。Table 2: Another preferred group of compounds of general formula I corresponds to general formula Ig
Figure A9880674200521
Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of the general formula Ig are thus disclosed.

表3：优选的另一组通式I化合物对应于通式Ih

Figure A9880674200522
其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Ih的特定化合物。Table 3: Another preferred group of compounds of general formula I corresponds to general formula Ih
Figure A9880674200522
Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of the general formula Ih are thus disclosed.

表4：优选的另一组通式I化合物对应于通式Ii

Figure A9880674200523
其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Ii的特定化合物。Table 4: Another preferred group of compounds of general formula I corresponds to general formula Ii
Figure A9880674200523
Wherein the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of general formula Ii are thus disclosed.

表5：优选的另一组通式I化合物对应于通式Ij其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Ij的特定化合物。Table 5: Another preferred group of compounds of general formula I corresponds to general formula Ij Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of the general formula Ij are thus disclosed.

表6：优选的另一组通式I化合物对应于通式Ik

Figure A9880674200531
其中对应取代基R1-R5和n的定义在表A中给出，这样公开了819种通式Ik的特定化合物。表A化合物号  R2  R1    R3  R4    R5          n.001    H    CH3    H    H      Cl           0.002    H    CH3    H    H      F            0.003    H    CH3    H    H      Br           0.004    H    CH3    H    H      SO2Me       0.005    H    CH3    H    H      SMe          0.006    H    CH3    H    H      SO2NMe2    0.007    H    CH3    H    H      CF3         0.008    H    CH3    H    H      CH3         0.009    H    CH3    H    H      CH(CH3)2   0.010    H    CH3    H    H      NO2         0.011    H    CH3    H    H      OCH3        0.012    H    CH3    H    H      OCF2CF3    0.013    H    CH3    H    H      CN           0.014    H    CH3    H    H      Cl           1.015    H    CH3    H    H      F            1.016    H    CH3    H    H      Br           1.017    H    CH3    H    H      SO2Me       1.018    H    CH3    H    H      SMe          1.019    H    CH3    H    H      SO2NMe2    1.020    H    CH3    H    H      CF3         1化合物号  R2    R1      R3  R4     R5          n.021    H      CH3      H    H       CH3         1.022    H      CH3      H    H       CH(CH3)2   1.023    H      CH3      H    H       NO2         1.024    H      CH3      H    H       OCH3        1.025    H      CH3      H    H       OCF2CF3    1.026    H      CH3      H    H       CN           1.027    H      CH3      H    H       Cl           2.028    H      CH3      H    H       F            2.029    H      CH3      H    H       Br           2.030    H      CH3      H    H       SO2Me       2.031    H      CH3      H    H       SMe          2.032    H      CH3      H    H       SO2NMe2    2.033    H      CH3      H    H       CF3         2.034    H      CH3      H    H       CH3         2.035    H      CH3      H    H       CH(CH3)2   2.036    H      CH3      H    H       NO2         2.037    H      CH3      H    H       OCH3        2.038    H      CH3      H    H       OCF2CF3    2.039    H      CH3      H    H       CN           2.040    H    CH3CH2    H    H       Cl           0.041    H    CH3CH2    H    H       F            0.042    H    CH3CH2    H    H       Br           0.043    H    CH3CH2    H    H       SO2Me       0.044    H    CH3CH2    H    H       SMe          0.045    H    CH3CH2    H    H       SO2NMe2    0.046    H    CH3CH2    H    H       CF3         0.047    H    CH3CH2    H    H       CH3         0.048    H    CH3CH2    H    H       CH(CH3)2   0.049    H    CH3CH2    H    H       NO2         0.050    H    CH3CH2    H    H       OCH3        0.051    H    CH3CH2    H    H       OCF2CF3    0化合物号   R2    R1        R3  R4     R5         n.052     H      CH3CH2    H    H       CN          0.053     H      CH3CH2    H    H       Cl          1.054     H      CH3CH2    H    H       F           1.055     H      CH3CH2    H    H       Br          1.056     H      CH3CH2    H    H       SO2Me      1.057     H      CH3CH2    H    H       SMe         1.058     H      CH3CH2    H    H       SO2NMe2   1.059     H      CH3CH2    H    H       CF3        1.060     H      CH3CH2    H    H       CH3        1.061     H      CH3CH2    H    H       CH(CH3)2  1.062     H      CH3CH2    H    H       NO2        1.063     H      CH3CH2    H    H       OCH3       1.064     H      CH3CH2    H    H       OCF2CF3   1.065     H      CH3CH2    H    H       CN          1.066     H      CH3CH2    H    H       Cl          2.067     H      CH3CH2    H    H       F           2.068     H      CH3CH2    H    H       Br          2.069     H      CH3CH2    H    H       SO2Me      2.070     H      CH3CH2    H    H       SMe         2.071     H      CH3CH2    H    H       SO2NMe2   2.072     H      CH3CH2    H    H       CF3        2.073     H      CH3CH2    H    H       CH3        2.074     H      CH3CH2    H    H       CH(CH3)2  2.075     H      CH3CH2    H    H       NO2        2.076     H      CH3CH2    H    H       OCH3       2.077     H      CH3CH2    H    H       OCF2CF3   2.078     H      CH3CH2    H    H       CN          2.079    CH3    CH3CH2    H    H       Cl          0.080    CH3    CH3CH2    H    H       F           0.081    CH3    CH3CH2    H    H       Br          0.082    CH3    CH3CH2    H    H       SO2Me      0化合物号  R2       R1       R3  R4   R5          n.083    CH3    CH3CH2    H    H     SMe          0.084    CH3    CH3CH2    H    H     SO2NMe2    0.085    CH3    CH3CH2    H    H     CF3         0.086    CH3    CH3CH2    H    H     CH3         0.087    CH3    CH3CH2    H    H     CH(CH3)2   0.088    CH3    CH3CH2    H    H     NO2         0.089    CH3    CH3CH2    H    H     OCH3        0.090    CH3    CH3CH2    H    H     OCF2CF3    0.091    CH3    CH3CH2    H    H     CN           0.092    CH3    CH3CH2    H    H     Cl           1.093    CH3    CH3CH2    H    H     F            1.094    CH3    CH3CH2    H    H     Br           1.095    CH3    CH3CH2    H    H     SO2Me       1.096    CH3    CH3CH2    H    H     SMe          1.097    CH3    CH3CH2    H    H     SO2NMe2    1.098    CH3    CH3CH2    H    H     CF3         1.099    CH3    CH3CH2    H    H     CH3         1.100    CH3    CH3CH2    H    H     CH(CH3)2   1.101    CH3    CH3CH2    H    H     NO2         1.102    CH3    CH3CH2    H    H     OCH3        1.103    CH3    CH3CH2    H    H     OCF2CF3    1.104    CH3    CH3CH2    H    H     CN           1.105    CH3    CH3CH2    H    H     Cl           2.106    CH3    CH3CH2    H    H     F            2.107    CH3    CH3CH2    H    H     Br           2.108    CH3    CH3CH2    H    H     SO2Me       2.109    CH3    CH3CH2    H    H     SMe          2.110    CH3    CH3CH2    H    H     SO2NMe2    2.111    CH3    CH3CH2    H    H     CF3         2.112    CH3    CH3CH2    H    H     CH3         2.113    CH3    CH3CH2    H    H     CH(CH3)2   2化合物号  R2     R1       R3   R4    R5       n.114    CH3   CH3CH2   H     H       NO2       2.115    CH3   CH3CH2   H     H       OCH3      2.116    CH3   CH3CH2   H     H       OCF2CF3 2.117    CH3   CH3CH2   H     H       CN         2.118    H      CH3       H     CH3    Cl         0.119    H      CH3       H     CH3    F          0.120    H      CH3       H     CH3    Br         0.121    H      CH3       H     CH3    SO2Me     0.122    H      CH3       H     CH3    SMe        0.123    H      CH3       H     CH3    SO2NMe2 0.124    H      CH3       H     CH3    CF3       0.125    H      CH3       H     CH3    CH3       0.126    H      CH3       H     CH3    CH(CH3)20.127    H      CH3       H     CH3    NO2       0.128    H      CH3       H     CH3    OCH3      0.129    H      CH3       H     CH3    OCF2CF3 0.130    H      CH3       H     CH3    CN         0.131    H      CH3       H     CH3    Cl         1.132    H      CH3       H     CH3    F          1.133    H      CH3       H     CH3    Br         1.134    H      CH3       H     CH3    SO2Me     1.135    H      CH3       H     CH3    SMe        1.136    H      CH3       H     CH3    SO2NMe2  1.137    H      CH3       H     CH3    CF3       1.138    H      CH3       H     CH3    CH3       1.139    H      CH3       H     CH3    CH(CH3)2 1.140    H      CH3       H     CH3    NO2       1.141    H      CH3       H     CH3    OCH3      1.142    H      CH3       H     CH3    OCF2CF3  1.143    H      CH3       H     CH3    CN         1.144    H      CH3       H     CH3    Cl         2化合物号  R2  R1         R3   R4    R5       n.145    H    CH3        H     CH3    F          2.146    H    CH3        H     CH3    Br         2.147    H    CH3        H     CH3    SO2Me     2.148    H    CH3        H     CH3    SMe        2.149    H    CH3        H     CH3    SO2NMe2  2.150    H    CH3        H     CH3    CF3       2.151    H    CH3        H     CH3    CH3       2.152    H    CH3        H     CH3    CH(CH3)22.153    H    CH3        H     CH3    NO2       2.154    H    CH3        H     CH3    OCH3      2.155    H    CH3        H     CH3    OCF2CF3  2.156    H    CH3CH2    H     CH3    CN         2.157    H    CH3CH2    H     CH3    Cl         0.158    H    CH3CH2    H     CH3    F          0.159    H    CH3CH2    H     CH3    Br         0.160    H    CH3CH2    H     CH3    SO2Me     0.161    H    CH3CH2    H     CH3    SMe        0.162    H    CH3CH2    H     CH3    SO2NMe2  0.163    H    CH3CH2    H     CH3    CF3       0.164    H    CH3CH2    H     CH3    CH3       0.165    H    CH3CH2    H     CH3    CH(CH3)2 0.166    H    CH3CH2    H     CH3    NO2       0.167    H    CH3CH2    H     CH3    OCH3      0.168    H    CH3CH2    H     CH3    OCF2CF3  0.169    H    CH3CH2    H     CH3    CN         0.170    H    CH3CH2    H     CH3    Cl         1.171    H    CH3CH2    H     CH3    F          1.172    H    CH3CH2    H     CH3    Br         1.173    H    CH3CH2    H     CH3    SO2Me     1.174    H    CH3CH2    H     CH3    SMe        1.175    H    CH3CH2    H     CH3    SO2NMe2  1化合物号  R2    R1       R3   R4     R5       n.176    H    CH3CH2    H     CH3    CF3       1.177    H    CH3CH2    H     CH3    CH3       1.178    H    CH3CH2    H     CH3    CH(CH3)2 1.179    H    CH3CH2    H     CH3    NO2       1.180    H    CH3CH2    H     CH3    OCH3      1.181    H    CH3CH2    H     CH3    OCF2CF3  1.182    H    CH3CH2    H     CH3    CN         1.183    H    CH3CH2    H     CH3    Cl         2.184    H    CH3CH2    H     CH3    F          2.185    H    CH3CH2    H     CH3    Br         2.186    H    CH3CH2    H     CH3    SO2Me     2.187    H    CH3CH2    H     CH3    SMe        2.188    H    CH3CH2    H     CH3    SO2NMe2  2.189    H    CH3CH2    H     CH3    CF3       2.190    H    CH3CH2    H     CH3    CH3       2.191    H    CH3CH2    H     CH3    CH(CH3)2 2.192    H    CH3CH2    H     CH3    NO2       2.193    H    CH3CH2    H     CH3    OCH3      2.194    H    CH3CH2    H     CH3    OCF2CF3  2.195    H    CH3CH2    H     CH3    CN         2.196    CH3 CH3CH2    H     CH3    Cl         0.197    CH3 CH3CH2    H     CH3    F          0.198    CH3 CH3CH2    H     CH3    Br         0.199    CH3 CH3CH2    H     CH3    SO2Me     0.200    CH3 CH3CH2    H     CH3    SMe        0.201    CH3 CH3CH2    H     CH3    SO2NMe2  0.202    CH3 CH3CH2    H     CH3    CF3       0.203    CH3 CH3CH2    H     CH3    CH3       0.204    CH3 CH3CH2    H     CH3    CH(CH3)2 0.205    CH3 CH3CH2    H     CH3    NO2       0.206    CH3 CH3CH2    H     CH3    OCH3      0化合物号  R2        R1        R3   R4     R5       n.207    CH3    CH3CH2     H     CH3    OCF2CF3  0.208    CH3    CH3CH2     H     CH3    CN         0.209    CH3    CH3CH2     H     CH3    Cl         1.210    CH3    CH3CH2     H     CH3    F          1.211    CH3    CH3CH2     H     CH3    Br         1.212    CH3    CH3CH2     H     CH3    SO2Me     1.213    CH3    CH3CH2     H     CH3    SMe        1.214    CH3    CH3CH2     H     CH3    SO2NMe2  1.215    CH3    CH3CH2     H     CH3    CF3       1.216    CH3    CH3CH2     H     CH3    CH3       1.217    CH3    CH3CH2     H     CH3    CH(CH3)2 1.218    CH3    CH3CH2     H     CH3    NO2       1.219    CH3    CH3CH2     H     CH3    OCH3      1.220    CH3    CH9CH2     H     CH3    OCF2CF3  1.221    CH3    CH3CH2     H     CH3    CN         1.222    CH3    CH3CH2     H     CH3    Cl         2.223    CH3    CH3CH2     H     CH3    F          2.224    CH3    CH3CH2     H     CH3    Br         2.225    CH3    CH3CH2     H     CH3    SO2Me     2.226    CH3    CH3CH2     H     CH3    SMe        2.227    CH3    CH3CH2     H     CH3    SO2NMe2  2.228    CH3    CH3CH2     H     CH3    CF3       2.229    CH3    CH3CH2     H     CH3    CH3       2.230    CH3    CH3CH2     H     CH3    CH(CH3)2 2.231    CH3    CH3CH2     H     CH3    NO2       2.232    CH3    CH3CH2     H     CH3    OCH3      2.233    CH3    CH3CH2     H     CH3    OCF2CF3  2.234    CH3    CH3CH2     H     CH3    CN         2.235    CH3    CH3CH2     CH3  CH3    Cl         0.236    CH3    CH3CH2     CH3  CH3    F          0.237    CH3    CH3CH2     CH3  CH3    Br         0化合物号  R2        R1       R3    R4      R5       n.238    CH3    CH3CH2    CH3    CH3    SO2Me     0.239    CH3    CH3CH2    CH3    CH3    SMe        0.240    CH3    CH3CH2    CH3    CH3    SO2NMe2  0.241    CH3    CH3CH2    CH3    CH3    CF3       0.242    CH3    CH3CH2    CH3    CH3    CH3       0.243    CH3    CH3CH2    CH3    CH3    CH(CH3)2 0.244    CH3    CH3CH2    CH3    CH3    NO2       0.245    CH3    CH3CH2    CH3    CH3    OCH3      0.246    CH3    CH3CH2    CH3    CH3    OCF2CF3  0.247    CH3    CH3CH2    CH3    CH3    CN         0.248    CH3    CH3CH2    CH3    CH3    Cl         1.249    CH3    CH3CH2    CH3    CH3    F          1.250    CH3    CH3CH2    CH3    CH3    Br         1.251    CH3    CH3CH2    CH3    CH3    SO2Me     1.252    CH3    CH3CH2    CH3    CH3    SMe        1.253    CH3    CH3CH2    CH3    CH3    SO2NMe2  1.254    CH3    CH3CH2    CH3    CH3    CF3       1.255    CH3    CH3CH2    CH3    CH3    CH3       1.256    CH3    CH3CH2    CH3    CH3    CH(CH3)2 1.257    CH3    CH3CH2    CH3    CH3    NO2       1.258    CH3    CH3CH2    CH3    CH3    OCH3      1.259    CH3    CH3CH2    CH3    CH3    OCF2CF3  1.260    CH3    CH3CH2    CH3    CH3    CN         1.261    CH3    CH3CH2    CH3    CH3    Cl         2.262    CH3    CH3CH2    CH3    CH3    F          2.263    CH3    CH3CH2    CH3    CH3    Br         2.264    CH3    CH3CH2    CH3    CH3    SO2Me     2.265    CH3    CH3CH2    CH3    CH3    SMe        2.266    CH3    CH3CH2    CH3    CH3    SO2NMe2  2.267    CH3    CH3CH2    CH3    CH3    CF3       2.268    CH3    CH3CH2    CH3    CH3    CH3       2化合物号  R2     R1       R3     R4     R5       n.269    CH3   CH3CH2  CH3   CH3   CH(CH3)2  2.270    CH3   CH3CH2  CH3   CH3   NO2        2.271    CH3   CH3CH2  CH3   CH3   OCH3       2.272    CH3   CH3CH2  CH3   CH3   OCF2CF3   2.273    CH3   CH3CH2  CH3   CH3   CN          2.274    H      CH3       H      Cl     Cl          0.275    H      CH3       H      Cl     F           0.276    H      CH3       H      Cl     Br          0.277    H      CH3       H      Cl     SO2Me      0.278    H      CH3       H      Cl     SMe         0.279    H      CH3       H      Cl     SO2NMe2   0.280    H      CH3       H      Cl     CF3        0.281    H      CH3       H      Cl     CH3        0.282    H      CH3       H      Cl     CH(CH3)2  0.283    H      CH3       H      Cl     NO2        0.284    H      CH3       H      Cl     OCH3       0.285    H      CH3       H      Cl     OCF2CF3   0.286    H      CH3       H      Cl     CN          0.287    H      CH3       H      Cl     Cl          1.288    H      CH3       H      Cl     F           1.289    H      CH3       H      Cl     Br          1.290    H      CH3       H      Cl     SO2Me      1.291    H      CH3       H      Cl     SMe         1.292    H      CH3       H      Cl     SO2NMe2   1.293    H      CH3       H      Cl     CF3        1.294    H      CH3       H      Cl     CH3        1.295    H      CH3       H      Cl     CH(CH3)2  1.296    H      CH3       H      Cl     NO2        1.297    H      CH3       H      Cl     OCH3       1.298    H      CH3       H      Cl     OCF2CF3   1.299    H      CH3       H      Cl     CN          1化合物号  R2   R1      R3   R4   R5      n.300    H    CH3       H    Cl    Cl        2.301    H    CH3       H    Cl    F         2.302    H    CH3       H    Cl    Br        2.303    H    CH3       H    Cl    SO2Me    2.304    H    CH3       H    Cl    SMe       2.305    H    CH3       H    Cl    SO2NMe2 2.306    H    CH3       H    Cl    CF3      2.307    H    CH3       H    Cl    CH3      2.308    H    CH3       H    Cl    CH(CH3)22.309    H    CH3       H    Cl    NO2      2.310    H    CH3       H    Cl    OCH3     2.311    H    CH3       H    Cl    OCF2CF3 2.312    H    CH3       H    Cl    CN        2.313    H    CH3CH2   H    Cl    Cl        0.314    H    CH3CH2   H    Cl    F         0.315    H    CH3CH2   H    Cl    Br        0.316    H    CH3CH2   H    Cl    SO2Me    0.317    H    CH3CH2   H    Cl    SMe       0.318    H    CH3CH2   H    Cl    SO2NMe2 0.319    H    CH3CH2   H    Cl    CF3      0.320    H    CH3CH2   H    Cl    CH3      0.321    H    CH3CH2   H    Cl    CH(CH3)20.322    H    CH3CH2   H    Cl    NO2      0.323    H    CH3CH2   H    Cl    OCH3     0.324    H    CH3CH2   H    Cl    OCF2CF3 0.325    H    CH3CH2   H    Cl    CN        0.326    H    CH3CH2   H    Cl    Cl        1.327    H    CH3CH2   H    Cl    F         1.328    H    CH3CH2   H    Cl    Br        1.329    H    CH3CH2   H    Cl    SO2Me    1.330    H    CH3CH2   H    Cl    SMe       1化合物号  R2     R1        R3   R4    R5      n.331    H      CH3CH2    H    Cl    SO2NMe2  1.332    H      CH3CH2    H    Cl    CF3       1.333    H      CH3CH2    H    Cl    CH3       1.334    H      CH3CH2    H    Cl    CH(CH3)2 1.335    H      CH3CH2    H    Cl    NO2       1.336    H      CH3CH2    H    Cl    OCH3      1.337    H      CH3CH2    H    Cl    OCF2CF3  1.338    H      CH3CH2    H    Cl    CN         1.339    H      CH3CH2    H    Cl    Cl         2.340    H      CH3CH2    H    Cl    F          2.341    H      CH3CH2    H    Cl    Br         2.342    H      CH3CH2    H    Cl    SO2Me     2.343    H      CH3CH2    H    Cl    SMe        2.344    H      CH3CH2    H    Cl    SO2NMe2  2.345    H      CH3CH2    H    Cl    CF3       2.346    H      CH3CH2    H    Cl    CH3       2.347    H      CH3CH2    H    Cl    CH(CH3)2 2.348    H      CH3CH2    H    Cl    NO2       2.349    H      CH3CH2    H    Cl    OCH3      2.350    H      CH3CH2    H    Cl    OCF2CF3  2.351    H      CH3CH2    H    Cl    CN         2.352    CH3   CH3CH2    H    Cl    Cl         0.353    CH3   CH3CH2    H    Cl    F          0.354    CH3   CH3CH2    H    Cl    Br         0.355    CH3   CH3CH2    H    Cl    SO2Me     0.356    CH3   CH3CH2    H    Cl    SMe        0.357    CH3   CH3CH2    H    Cl    SO2NMe2  0.358    CH3   CH3CH2    H    Cl    CF3       0.359    CH3   CH3CH2    H    Cl    CH3       0.360    CH3   CH3CH2    H    Cl    CH(CH3)2 0.361    CH3   CH3CH2    H    Cl    NO2       0化合物号  R2     R1        R3   R4     R5       n.362    CH3    CH3CH2    H    Cl     OCH3      0.363    CH3    CH3CH2    H    Cl     OCF2CF3  0.364    CH3    CH3CH2    H    Cl     CN         0.365    CH3    CH3CH2    H    Cl     Cl         1.366    CH3    CH3CH2    H    Cl     F          1.367    CH3    CH3CH2    H    Cl     Br         1.368    CH3    CH3CH2    H    Cl     SO2Me     1.369    CH3    CH3CH2    H    Cl     SMe        1.370    CH3    CH3CH2    H    Cl     SO2CMe2  1.371    CH3    CH3CH2    H    Cl     CF3       1.372    CH3    CH3CH2    H    Cl     CH3       1.373    CH3    CH3CH2    H    Cl     CH(CH3)2 1.374    CH3    CH3CH2    H    Cl     NO2       1.375    CH3    CH3CH2    H    Cl     OCH3      1.376    CH3    CH3CH2    H    Cl     OCF2CF3  1.377    CH3    CH3CH2    H    Cl     CN         1.378    CH3    CH3CH2    H    Cl     Cl         2.379    CH3    CH3CH2    H    Cl     F          2.380    CH3    CH3CH2    H    Cl     Br         2.381    CH3    CH3CH2    H    Cl     SO2Me     2.382    CH3    CH3CH2    H    Cl     SMe        2.383    CH3    CH3CH2    H    Cl     SO2NMe2  2.384    CH3    CH3CH2    H    Cl     CF3       2.385    CH3    CH3CH2    H    Cl     CH3       2.386    CH3    CH3CH2    H    Cl     CH(CH3)2 2.387    CH3    CH3CH2    H    Cl     NO2       2.388    CH3    CH3CH2    H    Cl     OCH3      2.389    CH3    CH3CH2    H    Cl     OCF2CF3  2.390    CH3    CH3CH2    H    Cl     CN         2.391    H       CH3         H    H      Cl         0.392    H       CH3         H    H      F          0化合物号  R2   R1   R3   R4   R5      n.393    H    CH3    H    H    Br         0.394    H    CH3    H    H    SO2Me     0.395    H    CH3    H    H    SMe        0.396    H    CH3    H    H    SO2NMe2  0.397    H    CH3    H    H    CF3       0.398    H    CH3    H    H    CH3       0.399    H    CH3    H    H    CH(CH3)2 0.400    H    CH3    H    H    NO2       0.401    H    CH3    H    H    OCH3      0.402    H    CH3    H    H    OCF2CF3  0.403    H    CH3    H    H    CN         0.404    H    CH3    H    H    Cl         1.405    H    CH3    H    H    F          1.406    H    CH3    H    H    Br         1.407    H    CH3    H    H    SO2Me     1.408    H    CH3    H    H    SMe        1.409    H    CH3    H    H    SO2NMe2  1.410    H    CH3    H    H    CF3       1.411    H    CH3    H    H    CH3       1.412    H    CH3    H    H    CH(CH3)2 1.413    H    CH3    H    H    NO2       1.414    H    CH3    H    H    OCH3      1.415    H    CH3    H    H    OCF2CF3  1.416    H    CH3    H    H    CN         1.417    H    CH3    H    H    Cl         2.418    H    CH3    H    H    F          2.419    H    CH3    H    H    Br         2.420    H    CH3    H    H    SO2Me     2.421    H    CH3    H    H    SMe        2.422    H    CH3    H    H    SO2NMe2  2.423    H    CH3    H    H    CF3       2化合物号 R2   R1   R3   R4   R5        n.424     H    CH3    H    H    CH3         2.425     H    CH3    H    H    CH(CH3)2   2.426     H    CH3    H    H    NO2         2.427     H    CH3    H    H    OCH3        2.428     H    CH3    H    H    OCF2CF3    2.429     H    CH3    H    H    CN           2.430     H    CH2OH  H    H    Cl           0.431     H    CH2OH  H    H    F            0.432     H    CH2OH  H    H    Br           0.433     H    CH2OH  H    H    SO2Me       0.434     H    CH2OH  H    H    SMe          0.435     H    CH2OH  H    H    SO2NMe2    0.436     H    CH2OH  H    H    CF3         0.437     H    CH2OH  H    H    CH3         0.438     H    CH2OH  H    H    CH(CH3)2   0.439     H    CH2OH  H    H    NO2         0.440     H    CH2OH  H    H    OCH3        0.441     H    CH2OH  H    H    OCF2CF3    0.442     H    CH2OH  H    H    CN           0.443     H    CH2OH  H    H    Cl           1.444     H    CH2OH  H    H    F            1.445     H    CH2OH  H    H    Br           1.446     H    CH2OH  H    H    SO2Me       1.447     H    CH2OH  H    H    SMe          1.448     H    CH2OH  H    H    SO2NMe2    1.449     H    CH2OH  H    H    CF3         1.450     H    CH2OH  H    H    CH3         1.451     H    CH2OH  H    H    CH(CH3)2   1.452     H    CH2OH  H    H    NO2         1.453     H    CH2OH  H    H    OCH3        1.454     H    CH2OH  H    H    OCF2CF3    1化合物号  R2   R1     R3   R4   R5       n.455    H    CH2OH    H    H    CN          1.456    H    CH2OH    H    H    Cl          2.457    H    CH2OH    H    H    F           2.458    H    CH2OH    H    H    Br          2.459    H    CH2OH    H    H    SO2Me      2.460    H    CH2OH    H    H    SMe         2.461    H    CH2OH    H    H    SO2NMe2  2.462    H    CH2OH    H    H    CF3        2.463    H    CH2OH    H    H    CH3        2.464    H    CH2OH    H    H    CH(CH3)2  2.465    H    CH2OH    H    H    NO2        2.466    H    CH2OH    H    H    OCH3       2.467    H    CH2OH    H    H    OCF2CF3   2.468    H    CH2OH    H    H    CN          2.469    H    CO2CH3  H    H    Cl          0.470    H    CO2CH3  H    H    F           0.471    H    CO2CH3  H    H    Br          0.472    H    CO2CH3  H    H    SO2Me      0.473    H    CO2CH3  H    H    SMe         0.474    H    CO2CH3  H    H    SO2NMe2   0.475    H    CO2CH3  H    H    CF3        0.476    H    CO2CH3  H    H    CH3        0.477    H    CO2CH3  H    H    CH(CH3)2  0.478    H    CO2CH3  H    H    NO2        0.479    H    CO2CH3  H    H    OCH3       0.480    H    CO2CH3  H    H    OCF2CF3   0.481    H    CO2CH3  H    H    CN          0.482    H    CO2CH3  H    H    Cl          1.483    H    CO2CH3  H    H    F           1.484    H    CO2CH3  H    H    Br          1.485    H    CO2CH3  H    H    SO2Me      1化合物号  R2   R1        R3  R4   R5         n.486    H    CO2CH3    H    H    SMe          1.487    H    CO2CH3    H    H    SO2NMe2    1.488    H    CO2CH3    H    H    CF3         1.489    H    CO2CH3    H    H    CH3         1.490    H    CO2CH3    H    H    CH(CH3)2   1.491    H    CO2CH3    H    H    NO2         1.492    H    CO2CH3    H    H    OCH3        1.493    H    CO2CH3    H    H    OCF2CF3    1.494    H    CO2CH3    H    H    CN           1.495    H    CO2CH3    H    H    Cl           2.496    H    CO2CH3    H    H    F            2.497    H    CO2CH3    H    H    Br           2.498    H    CO2CH3    H    H    SO2Me       2.499    H    CO2CH3    H    H    SMe          2.500    H    CO2CH3    H    H    SO2NMe2    2.501    H    CO2CH3    H    H    CF3         2.502    H    CO2CH3    H    H    CH3         2.503    H    CO2CH3    H    H    CH(CH3)2   2.504    H    CO2CH3    H    H    NO2         2.505    H    CO2CH3    H    H    OCH3        2.506    H    CO2CH3    H    H    OCF2CF3    2.507    H    CO2CH3    H    H    CN           2.508    H    CH＝O       H    H    Cl           0.509    H    CH＝O       H    H    F            0.510    H    CH＝O       H    H    Br           0.511    H    CH＝O       H    H    SO2Me       0.512    H    CH＝O       H    H    SMe          0.513    H    CH＝O       H    H    SO2NMe2    0.514    H    CH＝O       H    H    CF3         0.515    H    CH＝O       H    H    CH3         0.516    H    CH＝O       H    H    CH(CH3)2   0化合物号  R2   R1      R3   R4  R5        n.517    H    CH＝O      H    H    NO2        0.518    H    CH＝O      H    H    OCH3       0.519    H    CH＝O      H    H    OCF2CF3   0.520    H    CH＝O      H    H    CN          0.521    H    CH＝O      H    H    Cl          1.522    H    CH＝O      H    H    F           1.523    H    CH＝O      H    H    Br          1.524    H    CH＝O      H    H    SO2        1.525    H    CH＝O      H    H    SMe         1.526    H    CH＝O      H    H    SO2NMe2   1.527    H    CH＝O      H    H    CF3        1.528    H    CH＝O      H    H    CH3        1.529    H    CH＝O      H    H    CH(CH3)2  1.530    H    CH＝O      H    H    NO2        1.531    H    CH＝O      H    H    OCH3       1.532    H    CH＝O      H    H    OCF2CF3   1.533    H    CH＝O      H    H    CN          1.534    H    CH＝O      H    H    Cl          2.535    H    CH＝O      H    H    F           2.536    H    CH＝O      H    H    Br          2.537    H    CH＝O      H    H    SO2Me      2.538    H    CH＝O      H    H    SMe         2.539    H    CH＝O      H    H    SO2NMe2   2.540    H    CH＝O      H    H    CF3        2.541    H    CH＝O      H    H    CH3        2.542    H    CH＝O      H    H    CH(CH3)2  2.543    H    CH＝O      H    H    NO2        2.544    H    CH＝O      H    H    OCH3       2.545    H    CH＝O      H    H    OCF2CF3   2.546    H    CH＝O      H    H    CN          2.547    H    CH＝NOCH3 H    H    Cl          0化合物号  R2   R1         R3   R4  R5        n.548    H    CH＝NOCH3    H    H    F           0.549    H    CH＝NOCH3    H    H    Br          0.550    H    CH＝NOCH3    H    H    SO2Me      0.551    H    CH＝NOCH3    H    H    SMe         0.552    H    CH＝NOCH3    H    H    SO2NMe2   0.553    H    CH＝NOCH3    H    H    CF3        0.554    H    CH＝NOCH3    H    H    CH3        0.555    H    CH＝NOCH3    H    H    CH(CH3)2  0.556    H    CH＝NOCH3    H    H    NO2        0.557    H    CH＝NOCH3    H    H    OCH3       0.558    H    CH＝NOCH3    H    H    OCF2CF3   0.559    H    CH＝NOCH3    H    H    CN          0.560    H    CH＝NOCH3    H    H    Cl          1.561    H    CH＝NOCH3    H    H    F           1.562    H    CH＝NOCH3    H    H    Br          1.563    H    CH＝NOCH3    H    H    SO2Me      1.564    H    CH＝NOCH3    H    H    SMe         1.565    H    CH＝NOCH3    H    H    SO2NMe2   1.566    H    CH＝NOCH3    H    H    CF3        1.567    H    CH＝NOCH3    H    H    CH3        1.568    H    CH＝NOCH3    H    H    CH(CH3)2  1.569    H    CH＝NOCH3    H    H    NO2        1.570    H    CH＝NOCH3    H    H    OCH3       1.571    H    CH＝NOCH3    H    H    OCF2CF3   1.572    H    CH＝NOCH3    H    H    CN          1.573    H    CH＝NOCH3    H    H    Cl          2.574    H    CH＝NOCH3    H    H    F           2.575    H    CH＝NOCH3    H    H    Br          2.576    H    CH＝NOCH3    H    H    SO2Me      2.577    H    CH＝NOCH3    H    H    SMe         2.578    H    CH＝NOCH3    H    H    SO2NMe2   2化合物号  R2   R1           R3  R4  R5         n.579    H    CH＝NOCH3     H    H    CF3         2.580    H    CH＝NOCH3     H    H    CH3         2.581    H    CH＝NOCH3     H    H    CH(CH3)2   2.582    H    CH＝NOCH3     H    H    NO2         2.583    H    CH＝NOCH3     H    H    OCH3        2.584    H    CH＝NOCH3     H    H    OCF2CF3    2.585    H    CH＝NOCH3     H    H    CN           2.586    H    CH2NH2       H    H    Cl           0.587    H    CH2NH2       H    H    F            0.588    H    CH2NH2       H    H    Br           0.589    H    CH2NH2       H    H    SO2Me       0.590    H    CH2NH2       H    H    SMe          0.591    H    CH2NH2       H    H    SO2NMe2    0.592    H    CH2NH2       H    H    CF3         0.593    H    CH2NH2       H    H    CH3         0.594    H    CH2NH2       H    H    CH(CH3)2   0.595    H    CH2NH2       H    H    NO2         0.596    H    CH2NH2       H    H    OCH3        0.597    H    CH2NH2       H    H    OCF2CF3    0.598    H    CH2NH2       H    H    CN           0.599    H    CH2NH2       H    H    Cl           1.600    H    CH2NH2       H    H    F            1.601    H    CH2NH2       H    H    Br           1.602    H    CH2NH2       H    H    SO2Me       1.603    H    CH2NH2       H    H    SMe          1.604    H    CH2NH2       H    H    SO2NMe2    1.605    H    CH2NH2       H    H    CF3         1.606    H    CH2NH2       H    H    CH3         1.607    H    CH2NH2       H    H    CH(CH3)2   1.608    H    CH2NH2       H    H    NO2         1.609    H    CH2NH2       H    H    OCH3        1Table 6: Another preferred group of compounds of general formula I corresponds to general formula Ik
Figure A9880674200531
Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table A, 819 specific compounds of the general formula Ik are thus disclosed. Compound No. in Table A R 2 R 1 R 3 R 4 R 5 n.001 H CH 3 H H Cl 0.002 H CH 3 H H F 0.003 H CH 3 H H Br 0.004 H CH 3 H H SO 2 Me 0.005 H CH 3 H H SMe 0.006 H CH 3 H H SO 2 NMe 2 0.007 H CH 3 H H CF 3 0.008 H CH 3 H H CH 3 0.009 H CH 3 H H CH(CH 3 ) 2 0.010 H CH 3 H H NO 2 0.011 H CH 3 H H OCH 3 0.012 H CH 3 H H OCF 2 CF 3 0.013 H CH 3 H H CN 0.014 H CH 3 H H Cl 1.015 H CH 3 H H F 1.016 H CH 3 H H Br 1.017 H CH 3 H H SO 2 Me 1.018 H CH 3 H H SMe 1.019 H CH 3 H H SO 2 NMe 2 1.020 H CH 3 H H CF 3 1 compound number R 2 R 1 R 3 R 4 R 5 n.021 H CH 3 H H CH 3 1.022 H CH 3 H H CH(CH 3 ) 2 1.023 H CH 3 H H NO 2 1.024 H CH 3 H H OCH 3 1.025 H CH 3 H H OCF 2 CF 3 1.026 H CH 3 H H CN 1.027 H CH 3 H H Cl 2.028 H CH 3 H H F 2.029 H CH 3 H H Br 2.030 H CH 3 H H SO 2 Me 2.031 H CH 3 H H SMe 2.032 H CH 3 H H SO 2 NMe 2 2.033 H CH 3 H H CF 3 2.034 H CH 3 H H CH 3 2.035 H CH 3 H H CH(CH 3 ) 2 2.036 H CH 3 H H NO 2 2.037 H CH 3 H HOCH 3 2.038 H CH 3 H H OCF 2 CF 3 2.039 H CH 3 H H CN 2.040 H CH 3 CH 2 H H Cl 0.041 H CH 3 CH 2 H H F 0.042 H CH 3 CH 2 H H Br 0.043 H CH 3 CH 2 H H SO 2 Me 0.044 H CH 3 CH 2 H H SMe 0.045 H CH 3 CH 2 H H SO 2 NMe 2 0.046 H CH 3 CH 2 H H CF 3 0.047 H CH 3 CH 2 H H CH 3 0.048 H CH 3 CH 2 H H CH(CH 3 ) 2 0.049 H CH 3 CH 2 H H NO 2 0.050 H CH 3 CH 2 H H OCH 3 0.051 H CH 3 CH 2 H H OCF 2 CF 3 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.052 H CH 3 CH 2 H H CN 0.053 H CH 3 CH 2 H H Cl 1.054 H CH 3 CH 2 H H F 1.055 H CH 3 CH 2 H H Br 1.056 H CH 3 CH 2 H H SO 2 Me 1.057 H CH 3 CH 2 H H SMe 1.058 H CH 3 CH 2 H H SO 2 NMe 2 1.059 H CH 3 CH 2 H H CF 3 1.060 H CH 3 CH 2 H H CH 3 1.061 H CH 3 CH 2 H H CH(CH 3 ) 2 1.062 H CH 3 CH 2 H H NO 2 1.063 H CH 3 CH 2 H H OCH 3 1.064 H CH 3 CH 2 H H OCF 2 CF 3 1.065 H CH 3 CH 2 H H CN 1.066 H CH 3 CH 2 H H Cl 2.067 H CH 3 CH 2 H H F 2.068 H CH 3 CH 2 H H Br 2.069 H CH 3 CH 2 H H SO 2 Me 2.070 H CH 3 CH 2 H H SMe 2.071 H CH 3 CH 2 H H SO 2 NMe 2 2.072 H CH 3 CH 2 H H CF 3 2.073 H CH 3 CH 2 H H CH 3 2.074 H CH 3 CH 2 H H CH(CH 3 ) 2 2.075 H CH 3 CH 2 H H NO 2 2.076 H CH 3 CH 2 H H OCH 3 2.077 H CH 3 CH 2 H H OCF 2 CF 3 2.078 H CH 3 CH 2 H H CN 2.079 CH 3 CH 3 CH 2 H H Cl 0.080 CH 3 CH 3 CH 2 H H F 0.081 CH 3 CH 3 CH 2 H H Br 0.082 CH 3 CH 3 CH 2 H H SO 2 Me 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.083 CH 3 CH 3 CH 2 H H SMe 0.084 CH 3 CH 3 CH 2 H H SO 2 NMe 2 0.085 CH 3 CH 3 CH 2 H H CF 3 0.086 CH 3 CH 3 CH 2 H H CH 3 0.087 CH 3 CH 3 CH 2 H H CH(CH 3 ) 2 0.088 CH 3 CH 3 CH 2 H H NO 2 0.089 CH 3 CH 3 CH 2 H H OCH 3 0.090 CH 3 CH 3 CH 2 H H OCF 2 CF 3 0.091 CH 3 CH 3 CH 2 H H CN 0.092 CH 3 CH 3 CH 2 H H Cl 1.093 CH 3 CH 3 CH 2 H H F 1.094 CH 3 CH 3 CH 2 H H Br 1.095 CH 3 CH 3 CH 2 H H SO 2 Me 1.096 CH 3 CH 3 CH 2 H H SMe 1.097 CH 3 CH 3 CH 2 H H SO 2 NMe 2 1.098 CH 3 CH 3 CH 2 H H CF 3 1.099 CH 3 CH 3 CH 2 H H CH 3 1.100 CH 3 CH 3 CH 2 H H CH(CH 3 ) 2 1.101 CH 3 CH 3 CH 2 H H NO 2 1.102 CH 3 CH 3 CH 2 H H OCH 3 1.103 CH 3 CH 3 CH 2 H H OCF 2 CF 3 1.104 CH 3 CH 3 CH 2 H H CN 1.105 CH 3 CH 3 CH 2 H H Cl 2.106 CH 3 CH 3 CH 2 H H F 2.107 CH 3 CH 3 CH 2 H H Br 2.108 CH 3 CH 3 CH 2 H H SO 2 Me 2.109 CH 3 CH 3 CH 2 H H SMe 2.110 CH 3 CH 3 CH 2 H H SO 2 NMe 2 2.111 CH 3 CH 3 CH 2 H H CF 3 2.112 CH 3 CH 3 CH 2 H H CH 3 2.113 CH 3 CH 3 CH 2 H H CH(CH 3 ) 2 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.114 CH 3 CH 3 CH 2 H H NO 2 2.115 CH 3 CH 3 CH 2 H H OCH 3 2.116 CH 3 CH 3 CH 2 H H OCF 2 CF 3 2.117 CH 3 CH 3 CH 2 H H CN 2.118 H CH 3 H CH 3 Cl 0.119 H CH 3 H CH 3 F 0.120 H CH 3 H CH 3 Br 0.121 H CH 3 H CH 3 SO 2 Me 0.122 H CH 3 H CH 3 SMe 0.123 H CH 3 H CH 3 SO 2 NMe 2 0.124 H CH 3 H CH 3 CF 3 0.125 H CH 3 H CH 3 CH 3 0.126 H CH 3 H CH 3 CH(CH 3 ) 2 0.127 H CH 3 H CH 3 NO 2 0.128 H CH 3 H CH 3 OCH 3 0.129 H CH 3 H CH 3 OCF 2 CF 3 0.130 H CH 3 H CH 3 CN 0.131 H CH 3 H CH 3 Cl 1.132 H CH 3 H CH 3 F 1.133 H CH 3 H CH 3 Br 1.134 H CH 3 H CH 3 SO 2 Me 1.135 H CH 3 H CH 3 SMe 1.136 H CH 3 H CH 3 SO 2 NMe 2 1.137 H CH 3 H CH 3 CF 3 1.138 H CH 3 H CH 3 CH 3 1.139 H CH 3 H CH 3 CH(CH 3 ) 2 1.140 H CH 3 H CH 3 NO 2 1.141 H CH 3 H CH 3 OCH 3 1.142 H CH 3 H CH 3 OCF 2 CF 3 1.143 H CH 3 H CH 3 CN 1.144 H CH 3 H CH 3 Cl 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.145 H CH 3 H CH 3 F 2.146 H CH 3 H CH 3 Br 2.147 H CH 3 H CH 3 SO 2 Me 2.148 H CH 3 H CH 3 SMe 2.149 H CH 3 H CH 3 SO 2 NMe 2 2.150 H CH 3 H CH 3 CF 3 2.151 H CH 3 H CH 3 CH 3 2.152 H CH 3 H CH 3 CH(CH 3 ) 2 2.153 H CH 3 H CH 3 NO 2 2.154 H CH 3 H CH 3 OCH 3 2.155 H CH 3 H CH 3 OCF 2 CF 3 2.156 H CH 3 CH 2 H CH 3 CN 2.157 H CH 3 CH 2 H CH 3 Cl 0.158 H CH 3 CH 2 H CH 3 F 0.159 H CH 3 CH 2 H CH 3 Br 0.160 H CH 3 CH 2 H CH 3 SO 2 Me 0.161 H CH 3 CH 2 H CH 3 SMe 0.162 H CH 3 CH 2 H CH 3 SO 2 NMe 2 0.163 H CH 3 CH 2 H CH 3 CF 3 0.164 H CH 3 CH 2 H CH 3 CH 3 0.165 H CH 3 CH 2 H CH 3 CH(CH 3 ) 2 0.166 H CH 3 CH 2 H CH 3 NO 2 0.167 H CH 3 CH 2 H CH 3 OCH 3 0.168 H CH 3 CH 2 H CH 3 OCF 2 CF 3 0.169 H CH 3 CH 2 H CH 3 CN 0.170 H CH 3 CH 2 H CH 3 Cl 1.171 H CH 3 CH 2 H CH 3 F 1.172 H CH 3 CH 2 H CH 3 Br 1.173 H CH 3 CH 2 H CH 3 SO 2 Me 1.174 H CH 3 CH 2 H CH 3 SMe 1.175 H CH 3 CH 2 H CH 3 SO 2 NMe 2 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.176 H CH 3 CH 2 H CH 3 CF 3 1.177 H CH 3 CH 2 H CH 3 CH 3 1.178 H CH 3 CH 2 H CH 3 CH(CH 3 ) 2 1.179 H CH 3 CH 2 H CH 3 NO 2 1.180 H CH 3 CH 2 H CH 3 OCH 3 1.181 H CH 3 CH 2 H CH 3 OCF 2 CF 3 1.182 H CH 3 CH 2 H CH 3 CN 1.183 H CH 3 CH 2 H CH 3 Cl 2.184 H CH 3 CH 2 H CH 3 F 2.185 H CH 3 CH 2 H CH 3 Br 2.186 H CH 3 CH 2 H CH 3 SO 2 Me 2.187 H CH 3 CH 2 H CH 3 SMe 2.188 H CH 3 CH 2 H CH 3 SO 2 NMe 2 2.189 H CH 3 CH 2 H CH 3 CF 3 2.190 H CH 3 CH 2 H CH 3 CH 3 2.191 H CH 3 CH 2 H CH 3 CH(CH 3 ) 2 2.192 H CH 3 CH 2 H CH 3 NO 2 2.193 H CH 3 CH 2 H CH 3 OCH 3 2.194 H CH 3 CH 2 H CH 3 OCF 2 CF 3 2.195 H CH 3 CH 2 H CH 3 CN 2.196 CH 3 CH 3 CH 2 H CH 3 Cl 0.197 CH 3 CH 3 CH 2 H CH 3 F 0.198 CH 3 CH 3 CH 2 H CH 3 Br 0.199 CH 3 CH 3 CH 2 H CH 3 SO 2 Me 0.200 CH 3 CH 3 CH 2 H CH 3 SMe 0.201 CH 3 CH 3 CH 2 H CH 3 SO 2 NMe 2 0.202 CH 3 CH 3 CH 2 H CH 3 CF 3 0.203 CH 3 CH 3 CH 2 H CH 3 CH 3 0.204 CH 3 CH 3 CH 2 H CH 3 CH(CH 3 ) 2 0.205 CH 3 CH 3 CH 2 H CH 3 NO 2 0.206 CH 3 CH 3 CH 2 H CH 3 OCH 3 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.207 CH 3 CH 3 CH 2 H CH 3 OCF 2 CF 3 0.208 CH 3 CH 3 CH 2 H CH 3 CN 0.209 CH 3 CH 3 CH 2 H CH 3 Cl 1.210 CH 3 CH 3 CH 2 H CH 3 F 1.211 CH 3 CH 3 CH 2 H CH 3 Br 1.212 CH 3 CH 3 CH 2 H CH 3 SO 2 Me 1.213 CH 3 CH 3 CH 2 H CH 3 SMe 1.214 CH 3 CH 3 CH 2 H CH 3 SO 2 NMe 2 1.215 CH 3 CH 3 CH 2 H CH 3 CF 3 1.216 CH 3 CH 3 CH 2 H CH 3 CH 3 1.217 CH 3 CH 3 CH 2 H CH 3 CH(CH 3 ) 2 1.218 CH 3 CH 3 CH 2 H CH 3 NO 2 1.219 CH 3 CH 3 CH 2 H CH 3 OCH 3 1.220 CH 3 CH 9 CH 2 H CH 3 OCF 2 CF 3 1.221 CH 3 CH 3 CH 2 H CH 3 CN 1.222 CH 3 CH 3 CH 2 H CH 3 Cl 2.223 CH 3 CH 3 CH 2 H CH 3 F 2.224 CH 3 CH 3 CH 2 H CH 3 Br 2.225 CH 3 CH 3 CH 2 H CH 3 SO 2 Me 2.226 CH 3 CH 3 CH 2 H CH 3 SMe 2.227 CH 3 CH 3 CH 2 H CH 3 SO 2 NMe 2 2.228 CH 3 CH 3 CH 2 H CH 3 CF 3 2.229 CH 3 CH 3 CH 2 H CH 3 CH 3 2.230 CH 3 CH 3 CH 2 H CH 3 CH(CH 3 ) 2 2.231 CH 3 CH 3 CH 2 H CH 3 NO 2 2.232 CH 3 CH 3 CH 2 H CH 3 OCH 3 2.233 CH 3 CH 3 CH 2 H CH 3 OCF 2 CF 3 2.234 CH 3 CH 3 CH 2 H CH 3 CN 2.235 CH 3 CH 3 CH 2 CH 3 CH 3 Cl 0.236 CH 3 CH 3 CH 2 CH 3 CH 3 F 0.237 CH 3 CH 3 CH 2 CH 3 CH 3 Br 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.238 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 Me 0.239 CH 3 CH 3 CH 2 CH 3 CH 3 SMe 0.240 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 NMe 2 0.241 CH 3 CH 3 CH 2 CH 3 CH 3 CF 3 0.242 CH 3 CH 3 CH 2 CH 3 CH 3 CH 3 0.243 CH 3 CH 3 CH 2 CH 3 CH 3 CH(CH 3 ) 2 0.244 CH 3 CH 3 CH 2 CH 3 CH 3 NO 2 0.245 CH 3 CH 3 CH 2 CH 3 CH 3 OCH 3 0.246 CH 3 CH 3 CH 2 CH 3 CH 3 OCF 2 CF 3 0.247 CH 3 CH 3 CH 2 CH 3 CH 3 CN 0.248 CH 3 CH 3 CH 2 CH 3 CH 3 Cl 1.249 CH 3 CH 3 CH 2 CH 3 CH 3 F 1.250 CH 3 CH 3 CH 2 CH 3 CH 3 Br 1.251 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 Me 1.252 CH 3 CH 3 CH 2 CH 3 CH 3 SMe 1.253 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 NMe 2 1.254 CH 3 CH 3 CH 2 CH 3 CH 3 CF 3 1.255 CH 3 CH 3 CH 2 CH 3 CH 3 CH 3 1.256 CH 3 CH 3 CH 2 CH 3 CH 3 CH(CH 3 ) 2 1.257 CH 3 CH 3 CH 2 CH 3 CH 3 NO 2 1.258 CH 3 CH 3 CH 2 CH 3 CH 3 OCH 3 1.259 CH 3 CH 3 CH 2 CH 3 CH 3 OCF 2 CF 3 1.260 CH 3 CH 3 CH 2 CH 3 CH 3 CN 1.261 CH 3 CH 3 CH 2 CH 3 CH 3 Cl 2.262 CH 3 CH 3 CH 2 CH 3 CH 3 F 2.263 CH 3 CH 3 CH 2 CH 3 CH 3 Br 2.264 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 Me 2.265 CH 3 CH 3 CH 2 CH 3 CH 3 SMe 2.266 CH 3 CH 3 CH 2 CH 3 CH 3 SO 2 NMe 2 2.267 CH 3 CH 3 CH 2 CH 3 CH 3 CF 3 2.268 CH 3 CH 3 CH 2 CH 3 CH 3 CH 3 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.269 CH 3 CH 3 CH 2 CH 3 CH 3 CH (CH 3 ) 2 2.270 CH 3 CH 3 CH 2 CH 3 CH 3 NO 2 2.271 CH 3 CH 3 CH 2 CH 3 CH 3 OCH 3 2.272 CH 3 CH 3 CH 2 CH 3 CH 3 OCF 2 CF 3 2.273 CH 3 CH 3 CH 2 CH 3 CH 3 CN 2.274 H CH 3 H Cl Cl 0.275 H CH 3 H Cl F 0.276 H CH 3 H Cl Br 0.277 H CH 3 H Cl SO 2 Me 0.278 H CH 3 H Cl SMe 0.279 H CH 3 H Cl SO 2 NMe 2 0.280 H CH 3 H Cl CF 3 0.281 H CH 3 H Cl CH 3 0.282 H CH 3 H Cl CH(CH 3 ) 2 0.283 H CH 3 H Cl NO 2 0.284 H CH 3 H Cl OCH 3 0.285 H CH 3 H Cl OCF 2 CF 3 0.286 H CH 3 H Cl CN 0.287 H CH 3 H Cl Cl 1.288 H CH 3 H Cl F 1.289 H CH 3 H Cl Br 1.290 H CH 3 H Cl SO 2 Me 1.291 H CH 3 H Cl SMe 1.292 H CH 3 H Cl SO 2 NMe 2 1.293 H CH 3 H Cl CF 3 1.294 H CH 3 H Cl CH 3 1.295 H CH 3 H Cl CH(CH 3 ) 2 1.296 H CH 3 H Cl NO 2 1.297 H CH 3 H Cl OCH 3 1.298 H CH 3 H Cl OCF 2 CF 3 1.299 H CH 3 H Cl CN 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.300 H CH 3 H Cl Cl 2.301 H CH 3 H Cl F 2.302 H CH 3 H Cl Br 2.303 H CH 3 H Cl SO 2 Me 2.304 H CH 3 H Cl SMe 2.305 H CH 3 H Cl SO 2 NMe 2 2.306 H CH 3 H Cl CF 3 2.307 H CH 3 H Cl CH 3 2.308 H CH 3 H Cl CH(CH 3 ) 2 2.309 H CH 3 H Cl NO 2 2.310 H CH 3 H Cl OCH 3 2.311 H CH 3 H Cl OCF 2 CF 3 2.312 H CH 3 H Cl CN 2.313 H CH 3 CH 2 H Cl Cl 0.314 H CH 3 CH 2 H Cl F 0.315 H CH 3 CH 2 H Cl Br 0.316 H CH 3 CH 2 H Cl SO 2 Me 0.317 H CH 3 CH 2 H Cl SMe 0.318 H CH 3 CH 2 H Cl SO 2 NMe 2 0.319 H CH 3 CH 2 HCl CF 3 0.320 H CH 3 CH 2 H Cl CH 3 0.321 H CH 3 CH 2 H Cl CH(CH 3 ) 2 0.322 H CH 3 CH 2 H Cl NO 2 0.323 H CH 3 CH 2 H Cl OCH 3 0.324 H CH 3 CH 2 H Cl OCF 2 CF 3 0.325 H CH 3 CH 2 H Cl CN 0.326 H CH 3 CH 2 H Cl Cl 1.327 H CH 3 CH 2 H Cl F 1.328 H CH 3 CH 2 H Cl Br 1.329 H CH 3 CH 2 H Cl SO 2 Me 1.330 H CH 3 CH 2 H Cl SMe 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.331 H CH 3 CH 2 H Cl SO 2 NMe 2 1.332 H CH 3 CH 2 HCl CF 3 1.333 H CH 3 CH 2 HCl CH 3 1.334 H CH 3 CH 2 H Cl CH(CH 3 ) 2 1.335 H CH 3 CH 2 H Cl NO 2 1.336 H CH 3 CH 2 H Cl OCH 3 1.337 H CH 3 CH 2 H Cl OCF 2 CF 3 1.338 H CH 3 CH 2 H Cl CN 1.339 H CH 3 CH 2 H Cl Cl 2.340 H CH 3 CH 2 H Cl F 2.341 H CH 3 CH 2 H Cl Br 2.342 H CH 3 CH 2 H Cl SO 2 Me 2.343 H CH 3 CH 2 H Cl SMe 2.344 H CH 3 CH 2 H Cl SO 2 NMe 2 2.345 H CH 3 CH 2 H Cl CF 3 2.346 H CH 3 CH 2 H Cl CH 3 2.347 H CH 3 CH 2 H Cl CH(CH 3 ) 2 2.348 H CH 3 CH 2 H Cl NO 2 2.349 H CH 3 CH 2 H Cl OCH 3 2.350 H CH 3 CH 2 H Cl OCF 2 CF 3 2.351 H CH 3 CH 2 HCl CN 2.352 CH 3 CH 3 CH 2 H Cl Cl 0.353 CH 3 CH 3 CH 2 H Cl F 0.354 CH 3 CH 3 CH 2 H Cl Br 0.355 CH 3 CH 3 CH 2 H Cl SO 2 Me 0.356 CH 3 CH 3 CH 2 H Cl SMe 0.357 CH 3 CH 3 CH 2 H Cl SO 2 NMe 2 0.358 CH 3 CH 3 CH 2 H Cl CF 3 0.359 CH 3 CH 3 CH 2 H Cl CH 3 0.360 CH 3 CH 3 CH 2 H Cl CH (CH 3 ) 2 0.361 CH 3 CH 3 CH 2 H Cl NO 2 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.362 CH 3 CH 3 CH 2 H Cl OCH 3 0.363 CH 3 CH 3 CH 2 H Cl OCF 2 CF 3 0.364 CH 3 CH 3 CH 2 H Cl CN 0.365 CH 3 CH 3 CH 2 H Cl Cl 1.366 CH 3 CH 3 CH 2 H Cl F 1.367 CH 3 CH 3 CH 2 H Cl Br 1.368 CH 3 CH 3 CH 2 H Cl SO 2 Me 1.369 CH 3 CH 3 CH 2 H Cl SMe 1.370 CH 3 CH 3 CH 2 H Cl SO 2 CMe 2 1.371 CH 3 CH 3 CH 2 H Cl CF 3 1.372 CH 3 CH 3 CH 2 H Cl CH 3 1.373 CH 3 CH 3 CH 2 H Cl CH(CH 3 ) 2 1.374 CH 3 CH 3 CH 2 H Cl NO 2 1.375 CH 3 CH 3 CH 2 H Cl OCH 3 1.376 CH 3 CH 3 CH 2 H Cl OCF 2 CF 3 1.377 CH 3 CH 3 CH 2 H Cl CN 1.378 CH 3 CH 3 CH 2 H Cl Cl 2.379 CH 3 CH 3 CH 2 H Cl F 2.380 CH 3 CH 3 CH 2 H Cl Br 2.381 CH 3 CH 3 CH 2 H Cl SO 2 Me 2.382 CH 3 CH 3 CH 2 H Cl SMe 2.383 CH 3 CH 3 CH 2 H Cl SO 2 NMe 2 2.384 CH 3 CH 3 CH 2 H Cl CF 3 2.385 CH 3 CH 3 CH 2 H Cl CH 3 2.386 CH 3 CH 3 CH 2 H Cl CH(CH 3 ) 2 2.387 CH 3 CH 3 CH 2 H Cl NO 2 2.388 CH 3 CH 3 CH 2 H Cl OCH 3 2.389 CH 3 CH 3 CH 2 H Cl OCF 2 CF 3 2.390 CH 3 CH 3 CH 2 H Cl CN 2.391 H CH 3 H H Cl 0.392 H CH 3 H H F 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.393 H CH 3 H H Br 0.394 H CH 3 H H SO 2 Me 0.395 H CH 3 H H SMe 0.396 H CH 3 H H H SO 2 NMe 2 0.397 H CH 3 H H CF 3 0.398 H CH 3 H H CH 3 0.399 H CH 3 H H CH(CH 3 ) 2 0.400 H CH 3 H H NO 2 0.401 H CH 3 H H OCH 3 0.402 H CH 3 H H OCF 2 CF 3 0.403 H CH 3 H H CN 0.404 H CH 3 H H Cl 1.405 H CH 3 H H F 1.406 H CH 3 H H Br 1.407 H CH 3 H H SO 2 Me 1.408 H CH 3 H H SMe 1.409 H CH 3 H H SO 2 NMe 2 1.410 H CH 3 H H CF 3 1.411 H CH 3 H H CH 3 1.412 H CH 3 H H CH(CH 3 ) 2 1.413 H CH 3 H H NO 2 1.414 H CH 3 H H OCH 3 1.415 H CH 3 H H OCF 2 CF 3 1.416 H CH 3 H H CN 1.417 H CH 3 H H Cl 2.418 H CH 3 H H F 2.419 H CH 3 H H Br 2.420 H CH 3 H H SO 2 Me 2.421 H CH 3 H H SMe 2.422 H CH 3 H H SO 2 NMe 2 2.423 H CH 3 H H CF 3 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.424 H CH 3 H H CH 3 2.425 H CH 3 H H CH(CH 3 ) 2 2.426 H CH 3 H H NO 2 2.427 H CH 3 H H OCH 3 2.428 H CH 3 H H OCF 2 CF 3 2.429 H CH 3 H H CN 2.430 H CH 2 OH H H Cl 0.431 H CH 2 OH H H F 0.432 H CH 2 OH H H Br 0.433 H CH 2 OH H H SO 2 Me 0.434 H CH 2 OH H H SMe 0.435 H CH 2 OH H H SO 2 NMe 2 0.436 H CH 2 OH H H CF 3 0.437 H CH 2 OH H H CH 3 0.438 H CH 2 OH H H CH(CH 3 ) 2 0.439 H CH 2 OH H H NO 2 0.440 H CH 2 OH H H OCH 3 0.441 H CH 2 OH H H OCF 2 CF 3 0.442 H CH 2 OH H H CN 0.443 H CH 2 OH H H Cl 1.444 H CH 2 OH H H F 1.445 H CH 2 OH H H Br 1.446 H CH 2 OH H H SO 2 Me 1.447 H CH 2 OH H H SMe 1.448 H CH 2 OH H H SO 2 NMe 2 1.449 H CH 2 OH H H CF 3 1.450 H CH 2 OH H H CH 3 1.451 H CH 2 OH H H CH(CH 3 ) 2 1.452 H CH 2 OH H H NO 2 1.453 H CH 2 OH H H OCH 3 1.454 H CH 2 OH H H OCF 2 CF 3 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.455 H CH 2 OH H H CN 1.456 H CH 2 OH H H Cl 2.457 H CH 2 OH H H F 2.458 H CH 2 OH H H Br 2.459 H CH 2 OH H H SO 2 Me 2.460 H CH 2 OH H H SMe 2.461 H CH 2 OH H H SO 2 NMe 2 2.462 H CH 2 OH H H CF 3 2.463 H CH 2 OH H H CH 3 2.464 H CH 2 OH H H CH(CH 3 ) 2 2.465 H CH 2 OH H H NO 2 2.466 H CH 2 OH H H OCH 3 2.467 H CH 2 OH H H OCF 2 CF 3 2.468 H CH 2 OH H H CN 2.469 H CO 2 CH 3 H H Cl 0.470 H CO 2 CH 3 H H F 0.471 H CO 2 CH 3 H H Br 0.472 H CO 2 CH 3 H H SO 2 Me 0.473 H CO 2 CH 3 H H SMe 0.474 H CO 2 CH 3 H H SO 2 NMe 2 0.475 H CO 2 CH 3 H H CF 3 0.476 H CO 2 CH 3 H H CH 3 0.477 H CO 2 CH 3 H H CH(CH 3 ) 2 0.478 H CO 2 CH 3 H H NO 2 0.479 H CO 2 CH 3 H HOCH 3 0.480 H CO 2 CH 3 H H OCF 2 CF 3 0.481 H CO 2 CH 3 H H CN 0.482 H CO 2 CH 3 H H Cl 1.483 H CO 2 CH 3 H H F 1.484 H CO 2 CH 3 H H Br 1.485 H CO 2 CH 3 H H SO 2 Me 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.486 H CO 2 CH 3 H H SMe 1.487 H CO 2 CH 3 H H SO 2 NMe 2 1.488 H CO 2 CH 3 H H CF 3 1.489 H CO 2 CH 3 H H CH 3 1.490 H CO 2 CH 3 H H CH(CH 3 ) 2 1.491 H CO 2 CH 3 H H NO 2 1.492 H CO 2 CH 3 H H OCH 3 1.493 H CO 2 CH 3 H H OCF 2 CF 3 1.494 H CO 2 CH 3 H H CN 1.495 H CO 2 CH 3 H H Cl 2.496 H CO 2 CH 3 H H F 2.497 H CO 2 CH 3 H H Br 2.498 H CO 2 CH 3 H H SO 2 Me 2.499 H CO 2 CH 3 H H SMe 2.500 H CO 2 CH 3 H H SO 2 NMe 2 2.501 H CO 2 CH 3 H H CF 3 2.502 H CO 2 CH 3 H H CH 3 2.503 H CO 2 CH 3 H H CH(CH 3 ) 2 2.504 H CO 2 CH 3 H H NO 2 2.505 H CO 2 CH 3 H H OCH 3 2.506 H CO 2 CH 3 H H OCF 2 CF 3 2.507 H CO 2 CH 3 H H CN 2.508 H CH=OH H Cl 0.509 H CH=OH H F 0.510 H CH=OH H Br 0.511 H CH=OH H SO 2 Me 0.512 H CH=OH H SMe 0.513 H CH=OH H SO 2 NMe 2 0.514 H CH=OH H CF 3 0.515 H CH=OH H CH 3 0.516 H CH=OH H CH(CH 3 ) 2 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.517 H CH=OH H NO 2 0.518 H CH=OH H OCH 3 0.519 H CH=OH H OCF 2 CF 3 0.520 H CH=OH H CN 0.521 H CH=OH H Cl 1.522 H CH =OH H F 1.523 H CH=OH H Br 1.524 H CH=OH H SO 2 1.525 H CH=OH H SMe 1.526 H CH=OH H SO 2 NMe 2 1.527 H CH=OH H CF 3 1.528 H CH=OH H CH 3 1.529 H CH=OH H CH (CH 3 ) 2 1.530 H CH=OH H NO 2 1.531 H CH=OH H OCH 3 1.532 H CH=OH H OCF 2 CF 3 1.533 H CH=OH H CN 1.534 H CH=OH H Cl 2.535 H CH=OH H F 2.536 H CH=OH H Br 2.537 H CH=OH H SO 2 Me 2.538 H CH=OH H SMe 2.539 H CH=OH H SO 2 NMe 2 2.540 H CH=OH H CF 3 2.541 H CH=OH H CH 3 2.542 H CH=OH H CH(CH 3 ) 2 2.543 H CH=OH H NO 2 2.544 H CH=OH H OCH 3 2.545 H CH=OH H OCF 2 CF 3 2.546 H CH=OH H CN 2.547 H CH=NOCH 3 H H Cl 0 Compound No. R 2 R 1 R 3 R 4 R 5 n .548 H CH=NOCH 3 H H F 0.549 H CH=NOCH 3 H H Br 0.550 H CH=NOCH 3 H H SO 2 Me 0.551 H CH=NOCH 3 H H SMe 0.552 H CH=NOCH 3 H H SO 2 NMe 2 0.553 H CH=NOCH 3 H H CF 3 0.554 H CH=NOCH 3 H H CH 3 0.555 H CH=NOCH 3 H H CH(CH 3 ) 2 0.556 H CH=NOCH 3 H H NO 2 0.557 H CH=NOCH 3 H H OCH 3 0.558 H CH=NOCH 3 H H OCF 2 CF 3 0.559 H CH=NOCH 3 H H CN 0.560 H CH=NOCH 3 H H Cl 1.561 H CH=NOCH 3 H H F 1.562 H CH=NOCH 3 H H Br 1.563 H CH=NOCH 3 H H SO 2 Me 1.564 H CH= NOCH 3 H H SMe 1.565 H CH=NOCH 3 H H H SO 2 NMe 2 1.566 H CH=NOCH 3 H H CF 3 1.567 H CH=NOCH 3 H H CH 3 1.568 H CH=NOCH 3 H H CH(CH 3 ) 2 1.569 H CH= NOCH 3 H H NO 2 1.570 H CH＝NOCH 3 H H OCH 3 1.571 H CH＝NOCH 3 H H OCF 2 CF 3 1.572 H CH＝NOCH 3 H H CN 1.573 H CH＝NOCH 3 H H Cl 2.574 H CH＝NOCH 3 H H F 2.575 H CH=NOCH 3 H H Br 2.576 H CH=NOCH 3 H H SO 2 Me 2.577 H CH=NOCH 3 H H SMe 2.578 H CH=NOCH 3 H H SO 2 NMe 2 2 Compound No. R 2 R 1 R 3 R 4 R 5 n. 579 H CH=NOCH 3 H H CF 3 2.580 H CH=NOCH 3 H H CH 3 2.581 H CH=NOCH 3 H H CH(CH 3 ) 2 2.582 H CH=NOCH 3 H H NO 2 2.583 H CH=NOCH 3 H H OCH 3 2.584 H CH＝NOCH 3 H H OCF 2 CF 3 2.585 H CH＝NOCH 3 H H CN 2.586 H CH 2 NH 2 H H Cl 0.587 H CH 2 NH 2 H H F 0.588 H CH 2 NH 2 H H Br 0.589 H CH 2 NH 2 H H SO 2 Me 0.590 H CH 2 NH 2 H H SMe 0.591 H CH 2 NH 2 H H SO 2 NMe 2 0.592 H CH 2 NH 2 H H CF 3 0.593 H CH 2 NH 2 H H CH 3 0.594 H CH 2 NH 2 H H CH(CH 3 ) 2 0.595 H CH 2 NH 2 H H NO 2 0.596 H CH 2 NH 2 H H OCH 3 0.597 H CH 2 NH 2 H H OCF 2 CF 3 0.598 H CH 2 NH 2 H H CN 0.599 H CH 2 NH 2 H H Cl 1.600 H CH 2 NH 2 H H F 1.601 H CH 2 NH 2 H H Br 1.602 H CH 2 NH 2 H H SO 2 Me 1.603 H CH 2 NH 2 H H SMe 1.604 H CH 2 NH 2 H H SO 2 NMe 2 1.605 H CH 2 NH 2 H H CF 3 1.606 H CH 2 NH 2 H H CH 3 1.607 H CH 2 NH 2 H H CH(CH 3 ) 2 1.608 H CH 2 NH 2 H H NO 2 1.609 H CH 2 NH 2 H H OCH 3 1

化合物号    R2   R1        R3   R4   R5        nCompound No. R 2 R 1 R 3 R 4 R 5 n

.610    H    CH2NH2    H    H    OCF2CF3    1.610 H CH 2 NH 2 H H OCF 2 CF 3 1

.611    H    CH2NH2    H    H    CN           1.611 H CH 2 NH 2 H H CN 1

.612    H    CH2NH2    H    H    Cl           2.612 H CH 2 NH 2 H H Cl 2

.613    H    CH2NH2    H    H    F            2.613 H CH 2 NH 2 H H F 2

.614    H    CH2NH2    H    H    Br           2.614 H CH 2 NH 2 H H Br 2

.615    H    CH2NH2    H    H    SO2Me       2.615 H CH 2 NH 2 H H SO 2 Me 2

.616    H    CH2NH2    H    H    SMe          2.616 H CH 2 NH 2 H H SMe 2

.617    H    CH2NH2    H    H    SO2NMe2    2.617 H CH 2 NH 2 H H SO 2 NMe 2 2

.618    H    CH2NH2    H    H    CF3         2.618 H CH 2 NH 2 H H CF 3 2

.619    H    CH2NH2    H    H    CH3         2.619 H CH 2 NH 2 H H CH 3 2

.620    H    CH2NH2    H    H    CH(CH3)2   2.620 H CH 2 NH 2 H H CH(CH 3 ) 2 2

.621    H    CH2NH2    H    H    NO2         2.621 H CH 2 NH 2 H H NO 2 2

.622    H    CH2NH2    H    H    OCH3        2.622 H CH 2 NH 2 H H OCH 3 2

.623    H    CH2NH2    H    H    OCF2CF3    2.623 H CH 2 NH 2 H H OCF 2 CF 3 2

.624    H    CH2NH2    H    H    CN            2.624 H CH 2 NH 2 H H CN 2

.625    H    CN           H    H    Cl           0.625 H CN H H H Cl 0

.626    H    CN           H    H    F            0.626 H CN H H H F F 0

.627    H    CN           H    H    Br           0.627 H CN H H H Br 0

.628    H    CN           H    H    SO2Me       0.628 H CN H H SO 2 Me 0

.629    H    CN           H    H    SMe          0.629 H CN H H H SMe 0

.630    H    CN           H    H    SO2NMe2    0.630 H CN H H SO 2 NMe 2 0

.631    H    CN           H    H    CF3         0.631 H CN H H CF 3 0

.632    H    CN           H    H    CH3         0.632 H CN H H CH 3 0

.633    H    CN           H    H    CH(CH3)2   0.633 H CN H H CH(CH 3 ) 2 0

.634    H    CN           H    H    NO2         0.634 H CN H H NO 2 0

.635    H    CN           H    H    OCH3        0.635 H CN H H OCH 3 0

.636    H    CN           H    H    OCF2CF3    0.636 H CN H H OCF 2 CF 3 0

.637    H    CN           H    H    CN           0.637 H CN 0

.638    H    CN           H    H    Cl           1.638 H CN H H H Cl 1

.639    H    CN           H    H    F            1.639 H CN H H H F 1

.640    H    CN           H    H    Br           1化合物号  R2   R1        R3  R4   R5         n.641    H    CN           H    H    SO2Me       1.642    H    CN           H    H    SMe          1.643    H    CN           H    H    SO2NMe2    1.644    H    CN           H    H    CF3         1.645    H    CN           H    H    CH3         1.646    H    CN           H    H    CH(CH3)2   1.647    H    CN           H    H    NO2         1.648    H    CN           H    H    OCH3        1.649    H    CN           H    H    OCF2CF3    1.650    H    CN           H    H    CN           1.651    H    CN           H    H    Cl           2.652    H    CN           H    H    F            2.653    H    CN           H    H    Br           2.654    H    CN           H    H    SO2Me       2.655    H    CN           H    H    SMe          2.656    H    CN           H    H    SO2NMe2    2.657    H    CN           H    H    CF3         2.658    H    CN           H    H    CH3         2.659    H    CN           H    H    CH(CH3)2   2.660    H    CN           H    H    NO2         2.661    H    CN           H    H    OCH3        2.662    H    CN           H    H    OCF2CF3    2.663    H    CN           H    H    CN           2.664    H    CH(OH)CH3   H    H    Cl           0.665    H    CH(OH)CH3   H    H    F            0.666    H    CH(OH)CH3   H    H    Br           0.667    H    CH(OH)CH3   H    H    SO2Me       0.668    H    CH(OH)CH3   H    H    SMe          0.669    H    CH(OH)CH3   H    H    SO2NMe2    0.670    H    CH(OH)CH3   H    H    CF3         0.671    H    CH(OH)CH3   H    H    CH3         0化合物号  R2   R1         R3   R4   R5          n.672    H    CH(OH)CH3    H    H    CH(CH3)2     0.673    H    CH(OH)CH3    H    H    NO2           0.674    H    CH(OH)CH3    H    H    OCH3          0.675    H    CH(OH)CH3    H    H    OCF2CF3      0.676    H    CH(OH)CH3    H    H    CN             0.677    H    CH(OH)CH3    H    H    Cl             1.678    H    CH(OH)CH3    H    H    F              1.679    H    CH(OH)CH3    H    H    Br             1.680    H    CH(OH)CH3    H    H    SO2Me         1.681    H    CH(OH)CH3    H    H    SMe            1.682    H    CH(OH)CH3    H    H    SO2NMe2      1.683    H    CH(OH)CH3    H    H    CF3           1.684    H    CH(OH)CH3    H    H    CH3           1.685    H    CH(OH)CH3    H    H    CH(CH3)2     1.686    H    CH(OH)CH3    H    H    NO2           1.687    H    CH(OH)CH3    H    H    OCH3          1.688    H    CH(OH)CH3    H    H    OCF2CF3      1.689    H    CH(OH)CH3    H    H    CN             1.690    H    CH(OH)CH3    H    H    Cl             2.691    H    CH(OH)CH3    H    H    F              2.692    H    CH(OH)CH3    H    H    Br             2.693    H    CH(OH)CH3    H    H    SO2Me         2.694    H    CH(OH)CH3    H    H    SMe            2.695    H    CH(OH)CH3    H    H    SO2NMe2      2.696    H    CH(OH)CH3    H    H    CF3           2.697    H    CH(OH)CH3    H    H    CH3           2.698    H    CH(OH)CH3    H    H    CH(CH3)2     2.699    H    CH(OH)CH3    H    H    NO2           2.700    H    CH(OH)CH3    H    H    OCH3          2.701    H    CH(OH)CH3    H    H    OCF2CF3      2.702    H    CH(OH)CH3    H    H    CN             2化合物号  R2   R1         R3   R4  R5         n.703    H    CH＝CHCH3    H    H    Cl           0.704    H    CH＝CFCH3    H    H    F            0.705    H    CH＝CHCH3    H    H    Br           0.706    H    CH＝CHCH3    H    H    SO2Me       0.707    H    CH＝CHCH3    H    H    SMe          0.708    H    CH＝CHCH3    H    H    SO2NMe2    0.709    H    CH＝CHCH3    H    H    CF3         0.710    H    CH＝CHCH3    H    H    CH3         0.711    H    CH＝CHCH3    H    H    CH(CH3)2   0.712    H    CH＝CHCH3    H    H    NO2         0.713    H    CH＝CHCH3    H    H    OCH3        0.714    H    CH＝CHCH3    H    H    OCF2CF3    0.715    H    CH＝CHCH3    H    H    CN           0.716    H    CH＝CHCH3    H    H    Cl           1.717    H    CH＝CHCH3    H    H    F            1.718    H    CH＝CHCH3    H    H    Br           1.719    H    CH＝CHCH3    H    H    SO2Me       1.720    H    CH＝CHCH3    H    H    SMe          1.721    H    CH＝CHCH3    H    H    SO2NMe2    1.722    H    CH＝CHCH3    H    H    CF3         1.723    H    CH＝CHCH3    H    H    CH3         1.724    H    CH＝CHCH3    H    H    CH(CH3)2   1.725    H    CH＝CHCH3    H    H    NO2         1.726    H    CH＝CHCH3    H    H    OCH3        1.727    H    CH＝CHCH3    H    H    OCF2CF3    1.728    H    CH＝CHCH3    H    H    CN           1.729    H    CH＝CHCH3    H    H    Cl           2.730    H    CH＝CHCH3    H    H    F            2.731    H    CH＝CHCH3    H    H    Br           2.732    H    CH＝CHCH3    H    H    SO2Me       2.733    H    CH＝CHCH3    H    H    SMe          2化合物号  R2 R1             R3  R4   R5          n.734    H  CH＝CHCH3       H    H    SO2NMe2      2.735    H  CH＝CHCH3       H    H    CF3           2.736    H  CH＝CHCH3       H    H    CH3           2.737    H  CH＝CHCH3       H    H    CH(CH3)2     2.738    H  CH＝CHCH3       H    H    NO2           2.739    H  CH＝CHCH3       H    H    OCH3          2.740    H  CH＝CHCH3       H    H    OCF2CF3      2.741    H  CH＝CHCH3       H    H    CN             2.742    H  CH＝CHCO2CH3   H    H    Cl             0.743    H  CH＝CHCO2CH3   H    H    F              0.744    H  CH＝CHCO2CH3   H    H    Br             0.745    H  CH＝CHCO2CH3   H    H    SO2Me         0.746    H  CH＝CHCO2CH3   H    H    SMe            0.747    H  CH＝CHCO2CH3   H    H    SO2NMe2      0.748    H  CH＝CHCO2CH3   H    H    CF3           0.749    H  CH＝CHCO2CH3   H    H    CH3           0.750    H  CH＝CHCO2CH3   H    H    CH(CH3)2     0.751    H  CH＝CHCO2CH3   H    H    NO2           0.752    H  CH＝CHCO2CH3   H    H    OCH3          0.753    H  CH＝CHCO2CH3   H    H    OCF2CF3      0.754    H  CH＝CHCO2CH3   H    H    CN             0.755    H  CH＝CHCO2CH3   H    H    Cl             1.756    H  CH＝CHCO2CH3   H    H    F              1.757    H  CH＝CHCO2CH3   H    H    Br             1.758    H  CH＝CHCO2CH3   H    H    SO2Me         1.759    H  CH＝CHCO2CH3   H    H    SMe            1.760    H  CH＝CHCO2CH3   H    H    SO2NMe2      1.761    H  CH＝CHCO2CH3   H    H    CF3           1.762    H  CH＝CHCO2CH3   H    H    CH3           1.763    H  CH＝CHCO2CH3   H    H    CH(CH3)2     1.764    H  CH＝CHCO2CH3   H    H    NO2           1化合物号  R2   R1              R3   R4   R5      n.765    H     CH＝CHCO2CH3    H    H    OCH3      1.766    H     CH＝CHCO2CH3    H    H    OCF2CF3  1.767    H     CH＝CHCO2CH3    H    H    CN         1.768    H     CH＝CHCO2CH3    H    H    Cl         2.769    H     CH＝CHCO2CH3    H    H    F          2.770    H     CH＝CHCO2CH3    H    H    Br         2.771    H     CH＝CHCO2CH3    H    H    SO2Me     2.772    H     CH＝CHCO2CH3    H    H    SMe        2.773    H     CH＝CHCO2CH3    H    H    SO2NMe2  2.774    H     CH＝CHCO2CH3    H    H    CF3       2.775    H     CH＝CHCO2CH3    H    H    CH3       2.776    H     CH＝CHCO2CH3    H    H    CH(CH3)2 2.777    H     CH＝CHCO2CH3    H    H    NO2       2.778    H     CH＝CHCO2CH3    H    H    OCH3      2.779    H     CH＝CHCO2CH3    H    H    OCF2CF3  2.780    H     CH＝CHCO2CH3    H    H    CN         2.781    CH3  CH3              H    H    Cl         0.782    CH3  CH3              H    H    F          0.783    CH3  CH3              H    H    Br         0.784    CH3  CH3              H    H    SO2Me     0.785    CH3  CH3              H    H    SMe        0.786    CH3  CH3              H    H    SO2NMe2  0.787    CH3  CH3              H    H    CF3       0.788    CH3  CH3              H    H    CH3       0.789    CH3  CH3              H    H    CH(CH3)2 0.790    CH3  CH3              H    H    NO2       0.791    CH3  CH3              H    H    OCH3      0.792    CH3  CH3              H    H    OCF2CF3  0.793    CH3  CH3              H    H    CN         0.794    CH3  CH3              H    H    Cl         1.795    CH3  CH3              H    H    F          1化合物号  R2     R1     R3  R4   R5      n.796    CH3    CH3    H    H    Br         1.797    CH3    CH3    H    H    SO2Me     1.798    CH3    CH3    H    H    SMe        1.799    CH3    CH3    H    H    SO2NMe2  1.800    CH3    CH3    H    H    CF3       1.801    CH3    CH3    H    H    CH3       1.802    CH3    CH3    H    H    CH(CH3)2 1.803    CH3    CH3    H    H    NO2       1.804    CH3    CH3    H    H    OCH3      1.805    CH3    CH3    H    H    OCF2CF3  1.806    CH3    CH3    H    H    CN         1.807    CH3    CH3    H    H    Cl         2.808    CH3    CH3    H    H    F          2.809    CH3    CH3    H    H    Br         2.810    CH3    CH3    H    H    SO2Me     2.811    CH3    CH3    H    H    SMe        2.812    CH3    CH3    H    H    SO2NMe2  2.813    CH3    CH3    H    H    CF3       2.814    CH3    CH3    H    H    CH3       2.815    CH3    CH3    H    H    CH(CH3)2 2.816    CH3    CH3    H    H    NO2       2.817    CH3    CH3    H    H    OCH3      2.818    CH3    CH3    H    H    OCF2CF3  2.819    CH3    CH3    H    H    CN         2表7：通式II的化合物

Figure A9880674200801
化合物号  R2  R1  R3   R4   R5       n   n2 物理数据7.001    H   CH3   H     H    Cl         0   07.002    H   CH3   H     H    F          0   07.003    H   CH3   H     H    Br         0   07.004    H   CH3   H     H    SO2Me     0   07.005    H   CH3   H     H    SMe        0   07.006    H   CH3   H     H    SO2NMe2  0   07.007    H   CH3   H     H    CF3       0   07.008    H   CH3   H     H    CH3       0   07.009    H   CH3   H     H    CH(CH3)2 0   07.010    H   CH3   H     H    NO2       0   07.011    H   CH3   H     H    OCH3      0   07.012    H   CH3   H     H    OCF2CF3  0   07.013    H   CH3   H     H    CN         0   07.014    H   CH3   H     H    Cl         1   07.015    H   CH3   H     H    F          1   07.016    H   CH3   H     H    Br         1   07.017    H   CH3   H     H    SO2Me     1   07.018    H   CH3   H     H    SMe        1   07.019    H   CH3   H     H    SO2NMe2  1   07.020    H   CH3   H     H    CF3       1   07.021    H   CH3   H     H    CH3       1   07.022    H   CH3   H     H    CH(CH3)2 1   07.023    H   CH3   H     H    NO2       1   07.024    H   CH3   H     H    OCH3      1   07.025    H   CH3   H     H    OCF2CF3  1   0化合物号   R2  R1  R3  R4  R5       n   n2  物理数据7.026    H   CH3   H   H    CN         1   07.027    H   CH3   H   H    Cl         2   0   129-130℃7.028    H   CH3   H   H    F          2   07.029    H   CH3   H   H    Br         2   07.030    H   CH3   H   H    SO2Me     2   07.031    H   CH3   H   H    SMe        2   07.032    H   CH3   H   H    SO2NMe2  2   07.033    H   CH3   H   H    CF3       2   07.034    H   CH3   H   H    CH3       2   07.035    H   CH3   H   H    CH(CH3)2 2   07.036    H   CH3   H   H    NO2       2   07.037    H   CH3   H   H    OCH3      2   07.038    H   CH3   H   H    OCF2CF3  2   07.039    H   CH3   H   H    CN         2   07.040    H   CH3   H   H    Cl         0   07.041    H   CH3   H   H    F          0   07.042    H   CH3   H   H    Br         0   07.043    H   CH3   H   H    SO2Me     0   07.044    H   CH3   H   H    SMe        0   07.045    H   CH3   H   H    SO2NMe2  0   07.046    H   CH3   H   H    CF3       0   07.047    H   CH3   H   H    CH3       0   07.048    H   CH3   H   H    CH(CH3)2 0   07.049    H   CH3   H   H    NO2       0   07.050    H   CH3   H   H    OCH3      0   07.051    H   CH3   H   H    OCF2CF3  0   07.052    H   CH3   H   H    CN         0   07.053    H   CH3   H   H    Cl         1   07.054    H   CH3   H   H    F          1   07.055    H   CH3   H   H    Br         1   07.056    H   CH3   H   H    SO2Me     1   07.057    H   CH3   H   H    SMe        1   0化合物号  R2  R1  R3  R4  R5       n   n2 物理数据7.058    H   CH3   H   H    SO2NMe2  1   07.059    H   CH3   H   H    CF3       1   07.060    H   CH3   H   H    CH3       1   07.061    H   CH3   H   H    CH(CH3)2 1   07.062    H   CH3   H   H    NO2       1   07.063    H   CH3   H   H    OCH3      1   07.064    H   CH3   H   H    OCF2CF3  1   07.065    H   CH3   H   H    CN         1   07.066    H   CH3   H   H    Cl         2   07.067    H   CH3   H   H    F          2   07.068    H   CH3   H   H    Br         2   07.069    H   CH3   H   H    SO2Me     2   07.070    H   CH3   H   H    SMe        2   07.071    H   CH3   H   H    SO2NMe2  2   07.072    H   CH3   H   H    CF3       2   07.073    H   CH3   H   H    CH3       2   07.074    H   CH3   H   H    CH(CH3)2 2   07.075    H   CH3   H   H    NO2       2   07.076    H   CH3   H   H    OCH3      2   07.077    H   CH3   H   H    OCF2CF3  2   07.078    H   CH3   H   H    CN         2   07.079    H   CH3   H   H    Cl         0   17.080    H   CH3   H   H    F          0   17.081    H   CH3   H   H    Br         0   17.082    H   CH3   H   H    SO2Me     0   17.083    H   CH3   H   H    SMe        0   17.084    H   CH3   H   H    SO2NMe2  0   17.085    H   CH3   H   H    CF3       0   17.086    H   CH3   H   H    CH3       0   17.087    H   CH3   H   H    CH(CH3)2 0   17.088    H   CH3   H   H    NO2       0   17.089    H   CH3   H   H    OCH3      0   1化合物号  R2  R1  R3  R4 R5        n   n2 物理数据7.090    H   CH3   H   H    OCF2CF3  0   17.091    H   CH3   H   H    CN         0   17.092    H   CH3   H   H    Cl         1   17.093    H   CH3   H   H    F          1   17.094    H   CH3   H   H    Br         1   17.095    H   CH3   H   H    SO2Me     1   17.096    H   CH3   H   H    SMe        1   17.097    H   CH3   H   H    SO2NMe2  1   17.098    H   CH3   H   H    CF3       1   17.099    H   CH3   H   H    CH3       1   17.100    H   CH3   H   H    CH(CH3)2 1   17.101    H   CH3   H   H    NO2       1   17.102    H   CH3   H   H    OCH3      1   17.103    H   CH3   H   H    OCF2CF3  1   17.104    H   CH3   H   H    CN         1   17.105    H   CH3   H   H    Cl         2   17.106    H   CH3   H   H    F          2   17.107    H   CH3   H   H    Br         2   17.108    H   CH3   H   H    SO2Me     2   17.109    H   CH3   H   H    SMe        2   17.110    H   CH3   H   H    SO2NMe2  2   17.111    H   CH3   H   H    CF3       2   17.112    H   CH3   H   H    CH3       2   17.113    H   CH3   H   H    CH(CH3)2 2   17.114    H   CH3   H   H    NO2       2   17.115    H   CH3   H   H    OCH3      2   17.116    H   CH3   H   H    OCF2CF3  2   17.117    H   CH3   H   H    CN         2   17.118    H   CH3   H   H    Cl         0   27.119    H   CH3   H   H    F          0   27.120    H   CH3   H   H    Br         0   27.121    H   CH3   H   H    SO2Me     0   2化合物号  R2  R1   R3  R4  R5      n   n2 物理数据7.122    H   CH3   H   H    SMe        0   27.123    H   CH3   H   H    SO2NMe2  0   27.124    H   CH3   H   H    CF3       0   27.125    H   CH3   H   H    CH3       0   27.126    H   CH3   H   H    CH(CH3)2 0   27.127    H   CH3   H   H    NO2       0   27.128    H   CH3   H   H    OCH3      0   27.129    H   CH3   H   H    OCF2CF3  0   27.130    H   CH3   H   H    CN         0   27.131    H   CH3   H   H    Cl         1   27.132    H   CH3   H   H    F          1   27.133    H   CH3   H   H    Br         1   27.134    H   CH3   H   H    SO2Me     1   27.135    H   CH3   H   H    SMe        1   27.136    H   CH3   H   H    SO2NMe2  1   27.137    H   CH3   H   H    CF3       1   27.138    H   CH3   H   H    CH3       1   27.139    H   CH3   H   H    CH(CH3)2 1   27.140    H   CH3   H   H    NO2       1   27.141    H   CH3   H   H    OCH3      1   27.142    H   CH3   H   H    OCF2CF3  1   27.143    H   CH3   H   H    CN         1   27.144    H   CH3   H   H    Cl         2   27.145    H   CH3   H   H    F          2   27.146    H   CH3   H   H    Br         2   27.147    H   CH3   H   H    SO2Me     2   27.148    H   CH3   H   H    SMe        2   27.149    H   CH3   H   H    SO2NMe2  2   27.150    H   CH3   H   H    CF3       2   27.151    H   CH3   H   H    CH3       2   27.152    H   CH3   H   H    CH(CH3)2 2   27.153    H   CH3   H   H    NO2       2   2化合物号 R2   R1  R3  R4  R5        n   n2 物理数据7.154  H     CH3  H   H    OCH3       2   27.155  H     CH3  H   H    OCF2CF3   2   27.156  H     CH3  H   H    CN          2   27.157  CH3  CH3  H   H    Cl          0   07.158  CH3  CH3  H   H    F           0   07.159  CH3  CH3  H   H    Br          0   07.160  CH3  CH3  H   H    SO2Me      0   07.161  CH3  CH3  H   H    SMe         0   07.162  CH3  CH3  H   H    SO2NMe2   0   07.163  CH3  CH3  H   H    CF3        0   07.164  CH3  CH3  H   H    CH3        0   07.165  CH3  CH3  H   H    CH(CH3)2  0   07.166  CH3  CH3  H   H    NO2        0   07.167  CH3  CH3  H   H    OCH3       0   07.168  CH3  CH3  H   H    OCF2CF3   0   07.169  CH3  CH3  H   H    CN          0   07.170  CH3  CH3  H   H    Cl          1   07.171  CH3  CH3  H   H    F           1   07.172  CH3  CH3  H   H    Br          1   07.173  CH3  CH3  H   H    SO2Me      1   07.174  CH3  CH3  H   H    SMe         1   07.175  CH3  CH3  H   H    SO2NMe2   1   07.176  CH3  CH3  H   H    CF3        1   07.177  CH3  CH3  H   H    CH3        1   07.178  CH3  CH3  H   H    CH(CH3)2  1   07.179  CH3  CH3  H   H    NO2        1   07.180  CH3  CH3  H   H    OCH3       1   07.181  CH3  CH3  H   H    OCF2CF3   1   07.182  CH3  CH3  H   H    CN          1   07.183  CH3  CH3  H   H    Cl          2   07.184  CH3  CH3  H   H    F           2   07.185  CH3  CH3  H   H    Br          2   0化合物号 R2    R1    R3 R4   R5      n   n2 物理数据7.186   CH3   CH3   H   H    SO2Me     2   07.187   CH3   CH3   H   H    SMe        2   07.188   CH3   CH3   H   H    SO2NMe2  2   07.189   CH3   CH3   H   H    CF3       2   07.190   CH3   CH3   H   H    CH3       2   07.191   CH3   CH3   H   H    CH(CH3)2 2   07.192   CH3   CH3   H   H    NO2       2   07.193   CH3   CH3   H   H    OCH3      2   07.194   CH3   CH3   H   H    OCF2CF3  2   07.195   CH3   CH3   H   H    CN         2   0表8：优选的另一组通式I化合物对应于通式Im其中对应取代基R1-R5和n的定义在表B中给出，这样公开了78种通式Im的特定化合物。.640 H CN H H Br 1 Compound No. R 2 R 1 R 3 R 4 R 5 n.641 H CN H H SO 2 Me 1.642 H CN H H SMe 1.643 H CN H H SO 2 NMe 2 1.644 H CN H H CF 3 1.645 H CN H H CH 3 1.646 H CN H H CH(CH 3 ) 2 1.647 H CN H H NO 2 1.648 H CN H H OCH 3 1.649 H CN H H OCF 2 CF 3 1.650 H CN H H CN 1.651 H CN H H Cl 2.652 H CN H H F 2.653 H CN H H Br 2.654 H CN H H SO 2 Me 2.655 H CN H H SMe 2.656 H CN H H SO 2 NMe 2 2.657 H CN H H CF 3 2.658 H CN H H CH 3 2.659 H CN H H CH(CH 3 ) 2 2.660 H CN H H NO 2 2.661 H CN H H OCH 3 2.662 H CN H H OCF 2 CF 3 2.663 H CN H H CN 2.664 H CH(OH)CH 3 H H Cl 0.665 H CH(OH)CH 3 H H F 0.666 H CH(OH)CH 3 H H Br 0.667 H CH(OH)CH 3 H H SO 2 Me 0.668 H CH(OH)CH 3 H H SMe 0.669 H CH(OH)CH 3 H H SO 2 NMe 2 0.670 H CH(OH)CH 3 H H CF 3 0.671 H CH(OH) CH 3 H H CH 3 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.672 H CH(OH)CH 3 H H CH(CH 3 ) 2 0.673 H CH(OH)CH 3 H H NO 2 0.674 H CH( OH)CH 3 H H OCH 3 0.675 H CH(OH)CH 3 H H OCF 2 CF 3 0.676 H CH(OH)CH 3 H H CN 0.677 H CH(OH)CH 3 H H Cl 1.678 H CH(OH)CH 3 H H F 1.679 H CH(OH)CH 3 H H Br 1.680 H CH(OH)CH 3 H H SO 2 Me 1.681 H CH(OH)CH 3 H H SMe 1.682 H CH(OH)CH 3 H H SO 2 NMe 2 1.683 H CH(OH) CH 3 H H CF 3 1.684 H CH(OH)CH 3 H H CH 3 1.685 H CH(OH)CH 3 H H CH(CH 3 ) 2 1.686 H CH(OH)CH 3 H H NO 2 1.687 H CH(OH)CH 3 H H OCH 3 1.688 H CH(OH)CH 3 H H OCF 2 CF 3 1.689 H CH(OH)CH 3 H H CN 1.690 H CH(OH)CH 3 H H Cl 2.691 H CH(OH)CH 3 H H F 2.692 H CH(OH )CH 3 H H Br 2.693 H CH(OH)CH 3 H H SO 2 Me 2.694 H CH(OH)CH 3 H H SMe 2.695 H CH(OH)CH 3 H H SO 2 NMe 2 2.696 H CH(OH)CH 3 H H CF 3 2.697 H CH(OH)CH 3 H H CH 3 2.698 H CH(OH)CH 3 H H CH(CH 3 ) 2 2.699 H CH(OH)CH 3 H H NO 2 2.700 H CH(OH)CH 3 H HOCH 3 2.701 H CH(OH)CH 3 H H OCF 2 CF 3 2.702 H CH(OH)CH 3 H H CN 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.703 H CH=CHCH 3 H H Cl 0.704 H CH=CFCH 3 H H F 0.705 H CH=CHCH 3 H H Br 0.706 H CH=CHCH 3 H H SO 2 Me 0.707 H CH=CHCH 3 H H SMe 0.708 H CH=CHCH 3 H H SO 2 NMe 2 0.709 H CH=CHCH 3 H H CF 3 0.710 H CH=CHCH 3 H H CH 3 0.711 H CH=CHCH 3 H H CH(CH 3 ) 2 0.712 H CH=CHCH 3 H H NO 2 0.713 H CH=CHCH 3 H HOCH 3 0.714 H CH=CHCH 3 H H OCF 2 CF 3 0.715 H CH=CHCH 3 H H CN 0.716 H CH=CHCH 3 H H Cl 1.717 H CH=CHCH 3 H H F 1.718 H CH=CHCH 3 H H Br 1.719 H CH=CHCH 3 H H SO 2 Me 1.720 H CH=CHCH 3 H H SMe 1.721 H CH=CHCH 3 H H SO 2 NMe 2 1.722 H CH=CHCH 3 H H CF 3 1.723 H CH=CHCH 3 H H CH 3 1.724 H CH=CHCH 3 H H CH(CH 3 ) 2 1.725 H CH=CHCH 3 H H NO 2 1.726 HCH = CHCH3HHOCH3 1.727HCH = CHCH3HHOCF2CF31.728HCH = CHCH3HHCN1.729HCH = CHCH3HHCl2.730HCH = CHCH3HHF2.731HCH= CHCH3HHBr 2.732 H CH=CHCH 3 H H SO 2 Me 2.733 H CH=CHCH 3 H H SMe 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.734 H CH=CHCH 3 H H SO 2 NMe 2 2.735 H CH=CHCH 3 H H CF 3 2.736 H CH=CHCH 3 H H CH 3 2.737 H CH=CHCH 3 H H CH(CH 3 ) 2 2.738 H CH=CHCH 3 H H NO 2 2.739 H CH=CHCH 3 H H OCH 3 2.740 H CH=CHCH 3 H H OCF 2 CF 3 2.741 H CH=CHCH 3 H H CN 2.742 H CH=CHCO 2 CH 3 H H Cl 0.743 H CH=CHCO 2 CH 3 H H F 0.744 H CH=CHCO 2 CH 3 H H Br 0.745 H CH=CHCO 2 CH 3 H H SO 2 Me 0.746 H CH=CHCO 2 CH 3 H H SMe 0.747 H CH=CHCO 2 CH 3 H H SO 2 NMe 2 0.748 H CH=CHCO 2 CH 3 H H CF 3 0.749 H CH=CHCO 2 CH 3 H H CH 3 0.750 H CH=CHCO 2 CH 3 H H CH(CH 3 ) 2 0.751 H CH=CHCO 2 CH 3 H H NO 2 0.752 H CH=CHCO 2 CH 3 H HOCH 3 0.753 H CH=CHCO 2 CH 3 H H OCF 2 CF 3 0.754 H CH=CHCO 2 CH 3 H H CN 0.755 H CH=CHCO 2 CH 3 H H Cl 1.756 H CH=CHCO 2 CH 3 H H F 1.757 H CH=CHCO 2 CH 3 H H Br 1.758 H CH=CHCO 2 CH 3 H H H SO 2 Me 1.759 H CH=CHCO 2 CH 3 H H SMe 1.760 H CH=CHCO 2 CH 3 H H SO 2 NMe 2 1.761 H CH=CHCO 2 CH 3 H H CF 3 1.762 H CH=CHCO 2 CH 3 H H CH 3 1.763 H CH=CHCO 2 CH 3 H H CH(CH 3 ) 2 1.764 H CH=CHCO 2 CH 3 H H NO 2 1 compound number R 2 R 1 R 3 R 4 R 5 n.765 H CH=CHCO 2 CH 3 H HO CH 3 1.766 H CH= CHCO 2 CH 3 H H OCF 2 CF 3 1.767 H CH=CHCO 2 CH 3 H H CN 1.768 H CH=CHCO 2 CH 3 H H Cl 2.769 H CH=CHCO 2 CH 3 H H F 2.770 H CH=CHCO 2 CH 3 H H Br 2.771 H CH=CHCO 2 CH 3 H H SO 2 Me 2.772 H CH=CHCO 2 CH 3 H H SMe 2.773 H CH=CHCO 2 CH 3 H H SO 2 NMe 2 2.774 H CH=CHCO 2 CH 3 H H CF 3 2.775 H CH=CHCO 2 CH 3 H H CH 3 2.776 H CH=CHCO 2 CH 3 H H CH(CH 3 ) 2 2.777 H CH=CHCO 2 CH 3 H H NO 2 2.778 H CH=CHCO 2 CH 3 H H OCH 3 2.779 H CH=CHCO 2 CH 3 H H OCF 2 CF 3 2.780 H CH=CHCO 2 CH 3 H H CN 2.781 CH 3 CH 3 H H Cl 0.782 CH 3 CH 3 H H F 0.783 CH 3 CH 3 H H Br 0.784 CH 3 CH 3 H H SO 2 Me 0.785 CH 3 CH 3 H H SMe 0.786 CH 3 CH 3 H H SO 2 NMe 2 0.787 CH 3 CH 3 H H CF 3 0.788 CH 3 CH 3 H H CH 3 0.789 CH 3 CH 3 H H CH(CH 3 ) 2 0.790 CH 3 CH 3 H H NO 2 0.791 CH 3 CH 3 H H OCH 3 0.792 CH 3 CH 3 H H OCF 2 CF 3 0.793 CH 3 CH 3 H H CN 0.794 CH 3 CH 3 H H Cl 1.795 CH 3 CH 3 H H F 1 Compound No. R 2 R 1 R 3 R 4 R 5 n. 796 CH 3 CH 3 H H Br 1.797 CH 3 CH 3 H H SO 2 Me 1.798 CH 3 CH 3 H H SMe 1.799 CH 3 CH 3 H H SO 2 NMe 2 1.800 CH 3 CH 3 H H CF 3 1.801 CH 3 CH 3 H H CH 3 1.802 CH 3 CH 3 H H CH(CH 3 ) 2 1.803 CH 3 CH 3 H H NO 2 1.804 CH 3 CH 3 H H OCH 3 1.805 CH 3 CH 3 H H OCF 2 CF 3 1.806 CH 3 CH 3 H H CN 1.807 CH 3 CH 3 H H Cl 2.808 CH 3 CH 3 H H F 2.809 CH 3 CH 3 H H Br 2.810 CH 3 CH 3 H H SO 2 Me 2.811 CH 3 CH 3 H H SMe 2.812 CH 3 CH 3 H H SO 2 NMe 2 2.813 CH 3 CH 3 CH 3 CH H H CF 3 2.814 3 CH 3 H H CH 3 2.815 CH 3 CH 3 H H CH(CH 3 ) 2 2.816 CH 3 CH 3 H H NO 2 2.817 CH 3 CH 3 H H OCH 3 2.818 CH 3 CH 3 H H OCF 2 CF 3 2.819 CH 3 CH 3 H H CN 2 Table 7: Compounds of general formula II
Figure A9880674200801
Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.001 H CH 3 H H Cl 0 07.002 H CH 3 H H F 0 07.003 H CH 3 H H Br 0 07.004 H CH 3 H H SO 2 Me 0 07.005 H CH 3 H H SMe 0 07.006 H CH 3 H H SO 2 NMe 2 0 07.007 H CH 3 H H CF 3 0 07.008 H CH 3 H H CH 3 0 07.009 H CH 3 H H CH(CH 3 ) 2 0 07.010 H CH 3 H H NO 2 0 07.011 H CH 3 H H OCH 3 0 07.012 H CH 3 H H OCF 2 CF 3 0 07.013 H CH 3 H H CN 0 07.014 H CH 3 H H Cl 1 07.015 H CH 3 H H F 1 07.016 H CH 3 H H Br 1 07.017 H CH 3 H H SO 2 Me 1 07.018 H CH 3 H H SMe 1 07.019 H CH 3 H H SO 2 NMe 2 1 07.020 H CH 3 H H CF 3 1 07.021 H CH 3 H H CH 3 1 07.022 H CH 3 H H CH(CH 3 ) 2 1 07.023 H CH 3 H H NO 2 1 07.024 H CH 3 H H OCH 3 1 07.025 H CH 3 H H OCF 2 CF 3 1 0 Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.026 H CH 3 H H CN 1 07.027 H CH 3 H H Cl 2 0 129-130℃7.028 H CH 3 H H F 2 07.029 H CH 3 H H Br 2 07.030 H CH 3 H H SO 2 Me 2 07.031 H CH 3 H H SMe 2 07.032 H CH 3 H H SO 2 NMe 2 2 07.033 H CH 3 H H CF 3 2 07.034 H CH 3 H H CH 3 2 07.035 H CH 3 H H CH(CH 3 ) 2 2 07.036 H CH 3 H H NO 2 2 07.037 H CH 3 H H OCH 3 2 07.038 H CH 3 H H OCF 2 CF 3 2 07.039 H CH 3 H H CN 2 07.040 H CH 3 H H Cl 0 07.041 H CH 3 H H F 0 07.042 H CH 3 H H Br 0 07.043 H CH 3 H H SO 2 Me 0 07.044 H CH 3 H H SMe 0 07.045 H H CH 3 H SO 2 NMe 2 0 07.046 H CH 3 H H CF 3 0 07.047 H CH 3 H H CH 3 0 07.048 H CH 3 H H CH(CH 3 ) 2 0 07.049 H CH 3 H H NO 2 0 07.050 H CH 3 H H OCH 3 0 07.051 H CH 3 H H OCF 2 CF 3 0 07.052 H CH 3 H H CN 0 07.053 H CH 3 H H Cl 1 07.054 H CH 3 H H F 1 07.055 H CH 3 H H Br 1 07.056 H CH 3 H H SO 2 Me 1 07.057 H CH 3 H H SMe 1 0 Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.058 H CH 3 H H SO 2 NMe 2 1 07.059 H CH 3 H H CF 3 1 07.060 H CH 3 H H CH 3 1 07.061 H CH 3 H H CH(CH 3 ) 2 1 07.062 H CH 3 H H NO 2 1 07.063 H CH 3 H H OCH 3 1 07.064 H CH 3 H H OCF 2 CF 3 1 07.065 H CH 3 H H CN 1 07.066 H CH 3 H H Cl 2 07.067 H CH 3 H H F 2 07.068 H CH 3 H H Br 2 07.069 H CH 3 H H SO 2 Me 2 07.070 H CH 3 H H SMe 2 07.071 H CH 3 H H SO 2 NMe 2 2 07.072 H CH 3 H H CF 3 2 07.073 H CH 3 H H CH 3 2 07.074 H CH 3 H H CH(CH 3 ) 2 2 07.075 H CH 3 H H NO 2 2 07.076 H CH 3 H H OCH 3 2 07.077 H CH 3 H H OCF 2 CF 3 2 07.078 H CH 3 H H CN 2 07.079 H CH 3 H H Cl 0 17.080 H CH 3 H H F 0 17.081 H CH 3 H H Br 0 17.082 H CH 3 H H SO 2 Me 0 17.083 H CH 3 H H SMe 0 17.084 H CH 3 H H SO 2 NMe 2 0 17.085 H CH 3 H H CF 3 0 17.086 H CH 3 H H CH 3 0 17.087 H CH 3 H H CH(CH 3 ) 2 0 17.088 H CH 3 H H NO 2 0 17.089 H CH 3 H H OCH 3 0 1 Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 physical data 7.090 H CH 3 H H OCF 2 CF 3 0 17.091 H CH 3 H H CN 0 17.092 H CH 3 H H Cl 1 17.093 H CH 3 H H F 1 17.094 H CH 3 H H Br 1 17.095 H CH 3 H H SO 2 Me 1 17.096 H CH 3 H H SMe 1 17.097 H CH 3 H H SO 2 NMe 2 1 17.098 H CH 3 H H CF 3 1 17.099 H CH 3 H H CH 3 1 17.100 H CH 3 H H CH(CH 3 ) 2 1 17.101 H CH 3 H H NO 2 1 17.102 H CH 3 H H OCH 3 1 17.103 H CH 3 H H OCF 2 CF 3 1 17.104 H CH 3 H H CN 1 17.105 H CH 3 H H Cl 2 17.106 H CH 3 H H F 2 17.107 H CH 3 H H Br 8 H Br 2 17.1 CH 3 H H SO 2 Me 2 17.109 H CH 3 H H SMe 2 17.110 H CH 3 H H SO 2 NMe 2 2 17.111 H CH 3 H H CF 3 2 17.112 H CH 3 H H CH 3 2 17.113 H CH 3 H H CH(CH 3 ) 2 2 17.114 H CH 3 H H NO 2 2 17.115 H CH 3 H H OCH 3 2 17.116 H CH 3 H H OCF 2 CF 3 2 17.117 H CH 3 H H CN 2 17.118 H CH 3 H H Cl 0 27.119 H CH 3 H H F 0 H2 27.1 CH 3 H H Br 0 27.121 H CH 3 H H H SO 2 Me 0 2 Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.122 H CH 3 H H SMe 0 27.123 H CH 3 H H SO 2 NMe 2 0 27.124 H CH 3 H H CF 3 0 27.125 H CH 3 H H CH 3 0 27.126 H CH 3 H H CH(CH 3 ) 2 0 27.127 H CH 3 H H NO 2 0 27.128 H CH 3 H H OCH 3 0 27.129 H CH 3 H H OCF 2 CF 3 0 27.130 H CH 3 H H CN 0 27.131 H CH 3 H H Cl 1 27.132 H CH 3 H H F 1 27.133 H CH 3 H H Br 1 27.134 H CH 3 H H SO 2 Me 1 27.135 H CH 3 H H SMe 1 27.136 H H CH 3 H SO 2 NMe 2 1 27.137 H CH 3 H H CF 3 1 27.138 H CH 3 H H CH 3 1 27.139 H CH 3 H H CH(CH 3 ) 2 1 27.140 H CH 3 H H NO 2 1 27.141 H CH 3 H H OCH 3 1 27.142 H CH 3 H H OCF 2 CF 3 1 27.143 H CH 3 H H CN 1 27.144 H CH 3 H H Cl 2 27.145 H CH 3 H H F 2 27.146 H CH 3 H H Br 2 27.147 H CH 3 H H SO 2 Me 2 27.148 H CH 3 H H SMe 2 27.149 H CH 3 H H SO 2 NMe 2 2 27.150 H CH 3 H H CF 3 2 27.151 H CH 3 H H CH 3 2 27.152 H CH 3 H H CH(CH 3 ) 2 2 27.153 H CH 3 H H NO 2 2 2 compounds No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.154 H CH 3 H H OCH 3 2 27.155 H CH 3 H H OCF 2 CF 3 2 27.156 H CH 3 H H CN 2 27.157 CH 3 CH 3 H H Cl 0 07.158 CH 3 CH 3 H H F 0 07.159 CH 3 CH 3 H H Br 0 07.160 CH 3 CH 3 H H SO 2 Me 0 07.161 CH 3 CH 3 H H SMe 0 07.162 CH 3 CH 3 H H SO 2 NMe 2 0 07.163 CH 3 CH 3 H H CF 3 0 07.164 CH 3 CH 3 H H CH 3 0 07.165 CH 3 CH 3 H H CH(CH 3 ) 2 0 07.166 CH 3 CH 3 H H NO 2 0 07.167 CH 3 CH 3 H H OCH 3 0 07.168 CH 3 CH 3 H H OCF 2 CF 3 0 07.169 CH 3 CH 3 H H CN 0 07.170 CH 3 CH 3 H H Cl 1 07.171 CH 3 CH 3 H H F 1 07.172 CH 3 CH 3 H H Br 1 07.173 CH 3 CH 3 H H SO 2 Me 1 07.174 CH H 3 S Me CH 3 H 1 07.175 CH 3 CH 3 H H SO 2 NMe 2 1 07.176 CH 3 CH 3 H H CF 3 1 07.177 CH 3 CH 3 H H CH 3 1 07.178 CH 3 CH 3 H H CH( CH 3 ) 2 1 07.179 CH 3 CH 3 H H NO 2 1 07.180 CH 3 CH 3 H H OCH 3 1 07.181 CH 3 CH 3 H H OCF 2 CF 3 1 07.182 CH 3 CH 3 H H CN 1 07.183 CH 3 CH 3 H H Cl 2 07.184 CH 3 CH 3 H H F CH 2 07.185 3 CH 3 H H Br 2 0 Compound No. R 2 R 1 R 3 R 4 R 5 n n 2 Physical Data 7.186 CH 3 CH 3 H H SO 2 Me 2 07.187 CH 3 CH 3 H H SMe 2 07.188 CH 3 CH 3 H H SO 2 NMe 2 2 07.189 CH 3 CH 3 H H CF 3 2 07.190 CH 3 CH 3 H H CH 3 2 07.191 CH 3 CH 3 H H CH(CH 3 ) 2 2 07.192 CH 3 CH 3 H H NO 2 2 07.193 CH 3 CH 3 H H OCH 3 2 07.194 CH 3 CH 3 H H OCF 2 CF 3 2 07.195 CH 3 CH 3 H H CN 2 0 Table 8: Another preferred group of compounds of general formula I corresponding to general formula Im wherein the definitions of the corresponding substituents R 1 -R 5 and n are given in Table B, thus disclosing 78 specific compounds of general formula Im.

表9：优选的另一组通式I化合物对应于通式In

Figure A9880674200862
其中对应取代基R1-R5和n的定义在表B中给出，这样公开了78种通式In的特定化合物。Table 9: Another preferred group of compounds of general formula I corresponds to general formula In
Figure A9880674200862
Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table B, 78 specific compounds of the general formula In are thus disclosed.

表10：优选的另一组通式I化合物对应于通式Io其中对应取代基R1-R5和n的定义在表B中给出，这样公开了78种通式Io的特定化合物。Table 10: Another preferred group of compounds of general formula I corresponds to general formula Io Where the definitions of the corresponding substituents R 1 -R 5 and n are given in Table B, 78 specific compounds of general formula Io are thus disclosed.

表11：优选的另一组通式I化合物对应于通式Ip

Figure A9880674200872
其中对应取代基R1-R5和n的定义在表B中给出，这样公开了78种通式Ip的特定化合物。表B化合物号  R2  R1   R3 R4   R5       n.001    H   CH3   H   H    Cl          0.002    H   CH3   H   H    F           0.003    H   CH3   H   H    Br          0.004    H   CH3   H   H    SO2Me      0.005    H   CH3   H   H    SMe         0.006    H   CH3   H   H    SO2NMe2   0.007    H   CH3   H   H    CF3        0.008    H   CH3   H   H    CH3        0.009    H   CH3   H   H    CH(CH3)2  0.010    H   CH3   H   H    NO2        0.011    H   CH3   H   H    OCH3       0.012    H   CH3   H   H    OCF2CF3   0化合物号  R2    R1    R3  R4   R5      n.013    H     CH3    H    H    CN         0.014    H     CH3    H    H    Cl         1.015    H     CH3    H    H    F          1.016    H     CH3    H    H    Br         1.017    H     CH3    H    H    SO2Me     1.018    H     CH3    H    H    SMe        1.019    H     CH3    H    H    SO2NMe2  1.020    H     CH3    H    H    CF3       1.021    H     CH3    H    H    CH3       1.022    H     CH3    H    H    CH(CH3)2 1.023    H     CH3    H    H    NO2       1.024    H     CH3    H    H    OCH3      1.025    H     CH3    H    H    OCF2CF3  1.026    H     CH3    H    H    CN         1.027    H     CH3    H    H    Cl         2.028    H     CH3    H    H    F          2.029    H     CH3    H    H    Br         2.030    H     CH3    H    H    SO2Me     2.031    H     CH3    H    H    SMe        2.032    H     CH3    H    H    SO2NMe2  2.033    H     CH3    H    H    CF3       2.034    H     CH3    H    H    CH3       2.035    H     CH3    H    H    CH(CH3)2 2.036    H     CH3    H    H    NO2       2.037    H     CH3    H    H    OCH3      2.038    H     CH3    H    H    OCF2CF3  2.039    H     CH3    H    H    CN         2.040    CH3  CH3    H    H    Cl         0.041    CH3  CH3    H    H    F          0.042    CH3  CH3    H    H    Br         0.043    CH3  CH3    H    H    SO2Me     0.044    CH3  CH3    H    H    SMe        0化合物号  R2    R1    R3 R4  R5       n.045    CH3   CH3   H   H    SO2NMe2  0.046    CH3   CH3   H   H    CF3       0.047    CH3   CH3   H   H    CH3       0.048    CH3   CH3   H   H    CH(CH3)2 0.049    CH3   CH3   H   H    NO2       0.050    CH3   CH3   H   H    OCH3      0.051    CH3   CH3   H   H    OCF2CF3  0.052    CH3   CH3   H   H    CN         0.053    CH3   CH3   H   H    Cl         1.054    CH3   CH3   H   H    F          1.055    CH3   CH3   H   H    Br         1.056    CH3   CH3   H   H    SO2Me     1.057    CH3   CH3   H   H    SMe        1.058    CH3   CH3   H   H    SO2NMe2  1.059    CH3   CH3   H   H    CF3       1.060    CH3   CH3   H   H    CH2       1.061    CH3   CH3   H   H    CH(CH3)2 1.062    CH3   CH3   H   H    NO2       1.063    CH3   CH3   H   H    OCH3      1.064    CH3   CH3   H   H    OCF2CF3  1.065    CH3   CH3   H   H    CN         1.066    CH3   CH3   H   H    Cl         2.067    CH3   CH3   H   H    F          2.068    CH3   CH3   H   H    Br         2.069    CH3   CH3   H   H    SO2Me     2.070    CH3   CH3   H   H    SMe        2.071    CH3   CH3   H   H    SO2NMe2  2.072    CH3   CH3   H   H    CF3       2.073    CH3   CH3   H   H    CH3       2.074    CH3   CH3   H   H    CH(CH3)2 2.075    CH3   CH3   H   H    NO2       2.076    CH3   CH3   H   H    OCH3      2化合物号  R2   R1   R3  R4   R5       n.077    CH3   CH3   H   H    OCF2CF3  2.078    CH3   CH3   H   H    CN         2表12：通式Iq的化合物
Figure A9880674200901
化合物号 R6(C3) R7     R6(C5)   R18   n    物理数据12.001    CH3    CH3    H          H      012.002    CH3    CH3    CH3       H      012.003    CH3    CH3    CH＝CH2   H      012.004    CH3    CH3    Br         H      012.005    CH3    CH3    SMe        H      012.006    CH3    CH3    H          H      112.007    CH3    CH3    CH3       H      112.008    CH3    CH3    CH＝CH2   H      112.009    CH3    CH3    Br         H      112.01     CH3    CH3    SMe        H      112.011    CH3    CH3    H          H      2    159-161℃12.012    CH3    CH3    CH3       H      2    157-159℃12.013    CH3    CH3    CH＝CH2   H      212.014    CH3    CH3    Br         H      212.015    CH3    CH3    SMe        H      212.016    CH3    CH3    CH3       CH3   012.017    CH3    CH3    CH＝CH2   CH3   012.018    CH3    CH3    Br         CH3   0化合物号   R6(C3) R7    R6(C5)  R18   n    物理数据12.019    CH3    CH3    SMe      CH3    012.02     CH3    CH3    H        CH3    112.021    CH3    CH3    CH3     CH3    112.022    CH3    CH3    CH＝CH2 CH3    112.023    CH3    CH3    Br       CH3    112.024    CH3    CH3    SMe      CH3    112.025    CH3    CH3    H        CH3    212.026    CH3    CH3    CH3     CH3    212.027    CH3    CH3    CH＝CH2 CH3    212.028    CH3    CH3    Br       CH3    212.029    CH3    CH3    SMe      CH3    2Table 11: Another preferred group of compounds of general formula I corresponds to general formula Ip
Figure A9880674200872
Wherein the definitions of the corresponding substituents R 1 -R 5 and n are given in Table B, 78 specific compounds of the general formula Ip are thus disclosed. Compound No. in Table B R 2 R 1 R 3 R 4 R 5 n.001 H CH 3 H H Cl 0.002 H CH 3 H H F 0.003 H CH 3 H H Br 0.004 H CH 3 H H SO 2 Me 0.005 H CH 3 H H SMe 0.006 H CH 3 H H SO 2 NMe 2 0.007 H CH 3 H H CF 3 0.008 H CH 3 H H CH 3 0.009 H CH 3 H H CH(CH 3 ) 2 0.010 H CH 3 H H NO 2 0.011 H CH 3 H H OCH 3 0.012 H CH 3 H H OCF 2 CF 3 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.013 H CH 3 H H CN 0.014 H CH 3 H H Cl 1.015 H CH 3 H H F 1.016 H CH 3 H H Br 1.017 H CH 3 H H SO 2 Me 1.018 H CH 3 H H SMe 1.019 H CH 3 H H SO 2 NMe 2 1.020 H CH 3 H H CF 3 1.021 H CH 3 H H CH 3 1.022 H CH 3 H H CH(CH 3 ) 2 1.023 H CH 3 H H NO 2 1.024 H CH 3 H H OCH 3 1.025 H CH 3 H H OCF 2 CF 3 1.026 H CH 3 H H CN 1.027 H CH 3 H H Cl 2.028 H CH 3 H H F 2.029 H CH 3 H H Br 2.030 H CH 3 H H SO 2 Me 2.031 H CH 3 H H SMe 2.032 H CH 3 H H SO 2 NMe 2 2.033 H CH 3 H H CF 3 2.034 H CH 3 H H CH 3 2.035 H CH 3 H H CH(CH 3 ) 2 2.036 H CH 3 H H NO 2 2.037 H CH 3 H HOCH 3 2.038 H CH 3 H H OCF 2 CF 3 2.039 H CH 3 H H CN 2.040 CH 3 CH 3 H H Cl 0.041 CH 3 CH 3 H H F 0.042 CH 3 CH 3 H H Br 0.043 CH 3 CH 3 H H SO 2 Me 0.044 CH 3 CH 3 H H SMe 0 Compound No. R 2 R 1 R 3 R 4 R 5 n.045 CH 3 CH 3 H H SO 2 NMe 2 0.046 CH 3 CH 3 H H CF 3 0.047 CH 3 CH 3 H H CH 3 0.048 CH 3 CH 3 H H CH(CH 3 ) 2 0.049 CH 3 CH 3 H H NO 2 0.050 CH 3 CH 3 H H OCH 3 0.051 CH 3 CH 3 H H OCF 2 CF 3 0.052 CH 3 CH 3 H H CN 0.053 CH 3 CH 3 H H Cl 1.054 CH 3 CH 3 H H F 1.05 3 CH 3 H H Br 1.056 CH 3 CH 3 H H SO 2 Me 1.057 CH 3 CH 3 H H SMe 1.058 CH 3 CH 3 H H SO 2 NMe 2 1.059 CH 3 CH 3 H H CF 3 1.060 CH 3 CH 3 H H CH 2 1.061 CH 3 CH 3 H H CH(CH 3 ) 2 1.062 CH 3 CH 3 H H NO 2 1.063 CH 3 CH 3 H H OCH 3 1.064 CH 3 CH 3 H H OCF 2 CF 3 1.065 CH 3 CH 3 H H CN 1.066 CH 3 CH 3 H H Cl 2.067 CH 3 CH 3 H H F 2.068 CH 3 CH 3 H H Br 2.069 CH 3 CH 3 H H SO 2 Me 2.070 CH 3 CH 3 H H SMe 2.071 CH 3 CH 3 H H SO 2 NMe 2 2.072 CH 3 CH 3 H H CF 3 2.073 CH 3 CH 3 H H CH 3 2.074 CH 3 CH 3 H H CH(CH 3 ) 2 2.075 CH 3 CH 3 H H NO 2 2.076 CH 3 CH 3 H HOCH 3 2 Compound No. R 2 R 1 R 3 R 4 R 5 n.077 CH 3 CH 3 H H OCF 2 CF 3 2.078 CH 3 CH 3 H H CN 2 Table 12: Compounds of general formula Iq
Figure A9880674200901
Compound No. R 6 (C 3 ) R 7 R 6 (C 5 ) R 18 n Physical Data 12.001 CH 3 CH 3 H H 012.002 CH 3 CH 3 CH 3 H 012.003 CH 3 CH 3 CH=CH 2 H 012.004 CH 3 CH 3 Br H 012.005 CH 3 CH 3 SMe H 012.006 CH 3 CH 3 H H 112.007 CH 3 CH 3 CH 3 H 112.008 CH 3 CH 3 CH=CH 2 H 112.009 CH 3 CH 3 Br H 112.01 CH 3 CH 3 CH 3 H 112.01 CH 3 H H 2 159-161°C 12.012 CH 3 CH 3 CH 3 H 2 157-159°C 12.013 CH 3 CH 3 CH=CH 2 H 212.014 CH 3 CH 3 Br H 212.015 CH 3 CH 3 SMe H 212.016 CH 3 CH 3 CH 3 CH 3 012.017 CH 3 CH 3 CH=CH 2 CH 3 012.018 CH 3 CH 3 Br CH 3 0 Compound No. R 6 (C 3 ) R 7 R 6 (C 5 ) R 18 n Physical Data 12.019 CH 3 CH 3 SMe CH 3 012.02 CH 3 CH 3 H CH 3 112.021 CH 3 CH 3 CH 3 CH 3 112.022 CH 3 CH 3 CH=CH 2 CH 3 112.023 CH 3 CH 3 Br CH 3 112.024 CH 3 CH 3 SMe CH 3 112.0 CH 3 H CH 3 212.026 CH 3 CH 3 CH 3 CH 3 212.027 CH 3 CH 3 CH=CH 2 CH 3 212.028 CH 3 CH 3 Br CH 3 212.029 CH 3 CH 3 SMe CH 3 2

以上表12中的′R6(C3)′是指取代基R6键接于通式Iq化合物的碳原子3上；和因此′R6(C5)′是指取代基R6键接于通式Iq化合物的碳原子5上。表13：通式Ir的化合物

Figure A9880674200911
化合物号   R6   R6   R7   R7   R18     n    物理数据13.001    H    H    H    H    CH3          0    粘稠油13.002    H    H    H    H    CF3          013.003    H    H    H    H    CO2CH2CH3 0    粘稠油13.004    H    H    H    H    CH3          113.005    H    H    H    H    CF3          113.006    H    H    H    H    CO2CH2CH3 1化合物号   R6    R6   R7   R7    R18         n    物理数据13.007    H      H     H      H    CH3           2    129-132℃13.008    H      H     H      H    CF3           213.009    H      H     H      H    CO2CH2CH3  2    粘稠油13.010    CH3   H     H      H    H              013.011    CH3   H     H      H    CH3           013.012    CH3   H     H      H    CF3           013.013    CH3   H     H      H    CO2CH2CH3  013.014    CH3   H     H      H    H              113.015    CH3   H     H      H    CH3           113.016    CH3   H     H      H    CF3           113.017    CH3   H     H      H    CO2CH2CH3  113.018    CH3   H     H      H    H              213.019    CH3   H     H      H    CH3           213.020    CH3   H     H      H    CF3           213.021    CH3   H     H      H    CO2CH2CH3  213.022    CH3   H     CH3   H    H              0    139-140℃13.023    CH3   H     CH3   H    CH3           013.024    CH3   H     CH3   H    CF3           013.025    CH3   H     CH3   H    CO2CH2CH3  013.026    CH3   H     CH3   H    H              113.027    CH3   H     CH3   H    CH3           113.028    CH3   H     CH3   H    CF3           113.029    CH3   H     CH3   H    CO2CH2CH3  113.030    CH3   H     CH3   H    H              2    179-180℃13.031    CH3   H     CH3   H    CH3           213.032    CH3   H     CH3   H    CF3           213.033    CH3   H     CH3   H    CO2CH2CH3  213.034    CH3   CH3  CH3   H    H              0    粘稠油13.035    CH3   CH3  CH3   H    CH3           013.036    CH3   CH3  CH3   H    CF3           013.037    CH3   CH3  CH3   H    CO2CH2CH3  013.038    CH3   CH3  CH3   H    H              1    无定形化合物号   R6      R6     R7     R7   R18        n    物理数据13.039    CH3     CH3    CH3    H    CH3          113.040    CH3     CH3    CH3    H    CF3          113.041    CH3     CH3    CH3    H    CO2CH2CH3 113.042    CH3     CH3    CH3    H    H             2    树脂13.043    CH3     CH3    CH3    H    CH3          213.044    CH3     CH3    CH3    H    CF3          213.045    CH3     CH3    CH3    H    CO2CH2CH3 213.046    CH3     CH3    CH3    CH3 H             013.047    CH3     CH3    CH3    CH3 CH3          013.048    CH3     CH3    CH3    CH3 CF3          013.049    CH3     CH3    CH3    CH3 CO2CH2CH3 013.050    CH3     CH3    CH3    CH3 H             113.051    CH3     CH3    CH3    CH3 CH3          113.052    CH3     CH3    CH3    CH3 CF3          113.053    CH3     CH3    CH3    CH3 CO2CH2CH3 113.054    CH3     CH3    CH3    CH3 H             213.055    CH3     CH3    CH3    CH3 CH3          213.056    CH3     CH3    CH3    CH3 CF3          213.057    CH3     CH3    CH3    CH3 CO2CH2CH3 213.058    SCH3    H       CH3    H    H             0    125-128℃13.059    SO2CH3 H       CH3    H    H             0    粘稠油13.060    SCH3    H       CH3    H    CH3          013.061    SCH3    H       CH3    H    CF3          013.062    SCH3    H       CH3    H    CO2CH2H3  013.063    SCH3    H       CH3    H    H             113.064    SCH3    H       CH3    H    CH3          113.065    SCH3    H       CH3    H    CF3          113.066    SCH3    H       CH3    H    CO2CH2CH3 113.067    SCH3    H       CH3    H    H             213.068    SCH3    H       CH3    H    CH3          213.069    SCH3    H       CH3    H    CF3          213.070    SCH3    H       CH3    H    CO2CH2CH3 2化合物号  R6      R6     R7     R7    R18           n  物理数据13.071   SCH3    CH3   CH3    H       H              0  111-113℃13.072   SCH3    CH3   CH3    H       CH3           013.073   SCH3    CH3   CH3    H       CF3           013.074   SCH3    CH3   CH3    H       CO2CH2CH3  013.075   SCH3    CH3   CH3    H       H              113.076   SCH3    CH3   CH3    H       CH3           113.077   SCH3    CH3   CH3    H       CF3           113.078   SCH3    CH3   CH3    H       CO2CH2CH3  113.079   SCH3    CH3   CH3    H       H              2  树脂13.080   SO2CH3 CH3   CH3    H       H              2  244-246℃13.081   SCH3    CH3   CH3    H       CH3           213.082   SCH3    CH3   CH3    H       CF3           2  粘稠油(E异构体)13.083   SCH3    CH3   CH3    H       CF3           2  粘稠油(Z异构体)13.084   SCH3    CH3   CH3    H       CO2CH2CH3  213.085   SCH3    H      CH3    CH3    H              013.086   SCH3    H      CH3    CH3    CH3           013.087   SCH3    H      CH3    CH3    CF3           013.088   SCH3    H      CH3    CH3    CO2CH2CH3  013.089   SCH3    H      CH3    CH3    H              113.090   SCH3    H      CH3    CH3    CH3           113.091   SCH3    H      CH3    CH3    CF3           113.092   SCH3    H      CH3    CH3    CO2CH2CH3  113.093   SCH3    H      CH3    CH3    H              213.094   SCH3    H      CH3    CH3    CH3           213.095   SCH3    H      CH3    CH3    CF3           213.096   SCH3    H      CH3    CH3    CO2CH2CH3  213.097   SCH3    CH3   CH3    CH3    H              013.098   SCH3    CH3   CH3    CH3    CH3           013.099   SCH3    CH3   CH3    CH3    CF3           013.100   SCH3    CH3   CH3    CH3    CO2CH2CH3  013.101   SCH3    CH3   CH3    CH3    H              113.102   SCH3    CH3   CH3    CH3    CH3           1化合物号   R6      R6      R7     R7     R18          n    物理数据13.103    SCH3    CH3     CH3    CH3   CF3           113.104    SCH3    CH3     CH3    CH3   CO2CH2CH3  113.105    SCH3    CH3     CH3    CH3   H              213.106    SCH3    CH3     CH3    CH3   CH3           213.107    SCH3    CH3     CH3    CH3   CF3           213.108    SCH3    CH3     CH3    CH3   CO2CH2CH3  213.109    SCH3    SCH3    H       H      H              013.110    SCH3    SCH3    H       H      CH3           013.111    SCH3    SCH3    H       H      CF3           013.112    SCH3    SCH3    H       H      CO2CH2CH3  013.113    SCH3    SCH3    H       H      H              113.114    SCH3    SCH3    H       H      CH3           113.115    SCH3    SCH3    H       H      CF3           113.116    SCH3    SCH3    H       H      CO2CH2CH3  113.117    SCH3    SCH3    H       H      H              213.118    SCH3    SCH3    H       H      CH3           213.119    SCH3    SCH3    H       H      CF3           213.120    SCH3    SCH3    H       H      CO2CH2CH3  213.121    SCH3    SCH3    CH3    CH3   H              013.122    SCH3    SCH3    CH3    CH3   CH3           013.123    SCH3    SCH3    CH3    CH3   CF3           013.124    SCH3    SCH3    CH3    CH3   CO2CH2CH3  013.125    SCH3    SCH3    CH3    CH3   H              113.126    SCH3    SCH3    CH3    CH3   CH3           113.127    SCH3    SCH3    CH3    CH3   CF3           113.128    SCH3    SCH3    CH3    CH3   CO2CH2CH3  113.129    SCH3    SCH3    CH3    CH3   H              2    128-130℃(内消旋形式)13.130    SCH3    SCH3    CH3    CH3   H              2    189-192℃(E异构体)13.131    SCH3    SCH3    CH3    CH3   CH3           213.132    SCH3    SCH3    CH3    CH3   CF3           213.133    SCH3    SCH3    CH3    CH3   CO2CH2CH3  213.134    OCH3    H        H        H      H              0化合物号   R6      R6   R7   R7   R18          n    物理数据13.135    OCH3    H    H     H    CH3            013.136    OCH3    H    H     H    CF3            013.137    OCH3    H    H     H    CO2CH2CH3   013.138    OCH3    H    H     H    H               113.139    OCH3    H    H     H    CH3            113.140    OCH3    H    H     H    CF3            113.141    OCH3    H    H     H    CO2CH2CH3   113.142    OCH3    H    H     H    H               213.143    OCH3    H    H     H    CH3            213.144    OCH3    H    H     H    CF3            213.145    OCH3    H    H     H    CO2CH2CH3   213.146    OCH3    H    CH3  H    H               013.147    OCH3    H    CH3  H    CH3            013.148    OCH3    H    CH3  H    CF3            013.149    OCH3    H    CH3  H    CO2CH2CH3   013.150    OCH3    H    CH3  H    H               113.151    OCH3    H    CH3  H    CH3            113.152    OCH3    H    CH3  H    CF3            113.153    OCH3    H    CH3  H    CO2CH2CH3   113.154    OCH3    H    CH3  H    H               213.155    OCH3    H    CH3  H    CH3            213.156    OCH3    H    CH3  H    CF3            213.157    OCH3    H    CH3  H    CO2CH2CH3   213.158    OCH3    CH3 CH3  H    H               0    树脂(E异构体)13.159    OCH3    CH3 CH3  H    H               0    104-105℃(Z异构体)13.160    OCH3    CH3 CH3  H    CH3            013.161    OCH3    CH3 CH3  H    CF3            013.162    OCH3    CH3 CH3  H    CO2CH2CH3   013.163    OCH3    CH3 CH3  H    H               113.164    OCH3    CH3 CH3  H    CH3            113.165    OCH3    CH3 CH3  H    CF3            113.166    OCH3    CH3 CH3  H    CO2CH2CH3   1化合物号  R6      R6     R7     R7    R18          n  物理数据13.167   OCH3    CH3   CH3    H       H              2  树脂(Z异构体)13.168   OCH3    CH3   CH3    H       H              2  树脂(E异构体)13.169   OCH3    CH3   CH3    H       CH3           213.170   OCH3    CH3   CH3    H       CF3           213.171   OCH3    CH3   CH3    H       CO2CH2CH3  213.172   OCH3    CH3   CH3    CH3    H              013.173   OCH3    CH3   CH3    CH3    CH3           013.174   OCH3    CH3   CH3    CH3    CF3           013.175   OCH3    CH3   CH3    CH3    CO2CH2CH3  013.176   OCH3    CH3   CH3    CH3    H              113.177   OCH3    CH3   CH3    CH3    CH3           113.178   OCH3    CH3   CH3    CH3    CF3           113.179   OCH3    CH3   CH3    CH3    CO2CH2CH3  113.180   OCH3    CH3   CH3    CH3    H              213.181   OCH3    CH3   CH3    CH3    CH3           213.182   OCH3    CH3   CH3    CH3    CF3           213.183   OCH3    CH3   CH3    CH3    CO2CH2CH3  213.184   OCH3    H      OCH3   H       H              013.185   OCH3    H      OCH3   H       CH3           013.186   OCH3    H      OCH3   H       CF3           013.187   OCH3    H      OCH3   H       CO2CH2CH3  013.188   OCH3    H      OCH3   H       H              113.189   OCH3    H      OCH3   H       CH3           113.190   OCH3    H      OCH3   H       CF3           113.191   OCH3    H      OCH3   H       CO2CH2CH3  113.192   OCH3    H      OCH3   H       H              213.193   OCH3    H      OCH3   H       CH3           213.194   OCH3    H      OCH3   H       CF3           213.195   OCH3    H      OCH3   H       CO2CH2CH3  213.196   OCH3    CH3   OCH3   CH3    H             013.197   OCH3    CH3   OCH3   CH3    CH3          013.198   OCH3    CH3   OCH3   CH3    CF3          0化合物号  R6      R6     R7      R7     R18        n    物理数据13.199   OCH3    CH3    OCH3    CH3    CO2CH2CH3 013.200   OCH3    CH3    OCH3    CH3    H             113.201   OCH3    CH3    OCH3    CH3    CH3          113.202   OCH3    CH3    OCH3    CH3    CF3          113.203   OCH3    CH3    OCH3    CH3    CO2CH2CH3 113.204   OCH3    CH3    OCH3    CH3    H             213.205   OCH3    CH3    OCH3    CH3    CH3          213.206   OCH3    CH3    OCH3    CH3    CF3          213.207   OCH3    CH3    OCH3    CH3    CO2CH2CH3 213.208   SCH3    CH3    OCH3    H       H             0    无定形13.209   SCH3    CH3    OCH3    H       CH3          013.210   SCH3    CH3    OCH3    H       CF3          013.211   SCH3    CH3    OCH3    H       CO2CH2CH3 013.212   SCH3    CH3    OCH3    H       H             113.213   SCH3    CH3    OCH3    H       CH3          113.214   SCH3    CH3    OCH3    H       CF3          113.215   SCH3    CH3    OCH3    H       CO2CH2CH3 113.216   SCH3    CH3    OCH3    H       H             2    166-168℃13.217   SCH3    CH3    OCH3    H       CH3          213.218   SCH3    CH3    OCH3    H       CF3          213.219   SCH3    CH3    OCH3    H       CO2CH2CH3 213.220   SCH3    CH3    OCH3    CH3    H             013.221   SCH3    CH3    OCH3    CH3    CH3          013.222   SCH3    CH3    OCH3    CH3    CF3          013.223   SCH3    CH3    OCH3    CH3    CO2CH2CH3 013.224   SCH3    CH3    OCH3    CH3    H             113.225   SCH3    CH3    OCH3    CH3    CH3          113.226   SCH3    CH3    OCH3    CH3    CF3          113.227   SCH3    CH3    OCH3    CH3    CO2CH2CH3 113.228   SCH3    CH3    OCH3    CH3    H             213.229   SCH3    CH3    OCH3    CH3    CH3          213.230   SCH3    CH3    OCH3    CH3    CF3          2化合物号   R6     R6   R7     R7             R18            n    物理数据13.231    SCH3   CH3  OCH3   CH3            CO2CH2CH3   213.232    CH3    H     CH3    CH2CH＝CH2    H               013.233    CH3    H     CH3    CH2CH＝CH2    CH3            013.234    CH3    H     CH3    CH2CH＝CH2    CF3            013.235    CH3    H     CH3    CH2CH＝CH2    CO2CH2CH3   013.236    CH3    H     CH3    CH2CH＝CH2    H               113.237    CH3    H     CH3    CH2CH＝CH2    CH3            113.238    CH3    H     CH3    CH2CH＝CH2    CF3            113.239    CH3    H     CH3    CH2CH＝CH2    CO2CH2CH3   113.240    CH3    H     CH3    CH2CH＝CH2    H               2    粘稠油13.241    CH3    H     CH3    CH2CH＝CH2    CH3            213.242    CH3    H     CH3    CH2CH＝CH2    CF3            213.243    CH3    H     CH3    CH2CCH         CO2CH2CH3   213.244    CH3    H     CH3    CH2CCH         H               013.245    CH3    H     CH3    CH2CCH         CH3            013.246    CH3    H     CH3    CH2CCH         CF3            013.247    CH3    H     CH3    CH2CCH         CO2CH2CH3   013.248    CH3    H     CH3    CH2CCH         H               13.249    CH3    H     CH3    CH2CCH         CH3            113.250    CH3    H     CH3    CH2CCH         CF3            113.251    CH3    H     CH3    CH2CCH         CO2CH2CH3   113.252    CH3    H     CH3    CH2CCH         H               2    粘稠油13.253    CH3    H     CH3    CH2CCH         CH3            213.254    CH3    H     CH3    CH2CCH         CF3            213.255    CH3    H     CH3    CH2CCH         CO2CH2CH3   213.256    CH3    CH3  CH3    CH2CH＝CH2    H               013.257    CH3    CH3  CH3    CH2CH＝CH2    CH3            013.258    CH3    CH3  CH3    CH2CH＝CH2    CF3            013.259    CH3    CH3  CH3    CH2CH＝CH2    CO2CH2CH3   0化合物号   R6     R6     R7     R7            R18          n    物理数据13.260    CH3    CH3    CH3    CH2CH＝CH2   H             113.261    CH3    CH3    CH3    CH2CH＝CH2   CH3          113.262    CH3    CH3    CH3    CH2CH＝CH2   CF3          113.263    CH3    CH3    CH3    CH2CH＝CH2   CO2CH2CH3 113.264    CH3    CH3    CH3    CH2CH＝CH2   H             213.265    CH3    CH3    CH3    CH2CH＝CH2   CH3          213.266    CH3    CH3    CH3    CH2CH＝CH2   CF3          213.267    CH3    CH3    CH3    CH2CCH        CO2CH2CH3 213.268    CH3    CH3    CH3    CH2CCH        H             013.269    CH3    CH3    CH3    CH2CCH        CH3          013.270    CH3    CH3    CH3    CH2CCH        CF3          013.271    CH3    CH3    CH3    CH2CCH        CO2CH2CH3 013.272    CH3    CH3    CH3    CH2CCH        H             113.273    CH3    CH3    CH3    CH2CCH        CH3          113.274    CH3    CH3    CH3    CH2CCH        CF3          113.275    CH3    CH3    CH3    CH2CCH        CO2CH2CH3 113.276    CH3    CH3    CH3    CH2CCH        H             213.277    CH3    CH3    CH3    CH2CCH        CH3          213.278    CH3    CH3    CH3    CH2CCH        CF3          213.279    CH3    CH3    CH3    CH2CCH        CO2CH2CH3 2'R 6 (C 3 )' in the above Table 12 means that the substituent R 6 is bonded to carbon atom 3 of the compound of general formula Iq; and therefore 'R 6 (C 5 )' means that the substituent R 6 is bonded to On carbon atom 5 of the compound of general formula Iq. Table 13: Compounds of general formula Ir
Figure A9880674200911
Compound No. R 6 R 6 R 7 R 7 R 18 n Physical data 13.001 H H H H CH 3 0 Viscous oil 13.002 H H H H CF 3 013.003 H H H H CO 2 CH 2 CH 3 0 Viscous oil 13.004 H H H H CH 3 113.005 H H H H CF 3 H H CO 3 113.006 H H 2 CH 2 CH 3 1 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical data 13.007 H H H H CH 3 2 129-132℃13.008 H H H H CF 3 213.009 H H H H CO 2 CH 2 CH 3 2 Viscous oil 13.010 CH 3 H H H H 013.011 CH 3 H H C 3 013.012 CH 3 H H CF 3 013.013 CH 3 H H CO 2 CH 2 CH 3 013.014 CH 3 H H H H H H H H H H H H H H H H H Ch 3 113.016 H H CF 3 113.017 CH H H H H CH 2 CH 3 113.018 CH 3 H H H H 213.019 CH 3 H H H CH 3 213.020 CH 3 H H H CF 3 213.021 CH 3 H H H CO 2 CH 2 CH 3 213.022 CH 3 H CH 3 H H 0 139-140°C 13.023 CH 3 H CH 3 H CH H 3 4 013. 3 H CF 3 013.025 CH 3 H CH 3 H CO 2 CH 2 CH 3 013.026 CH 3 H CH 3 H H 113.027 CH 3 H CH 3 H CH 3 113.028 CH 3 H CH 3 H CF 3 113.029 CH 3 H CH 3 H CO 2 CH 2 CH 3 113.030 CH 3 H CH 3 H H 2 179-180°C 13.031 CH 3 H CH 3 H CH 3 213.032 CH 3 H CH 3 H CF 3 213.033 CH 3 H CH 3 H CO 2 CH 2 CH 3 213.034 CH 3 CH 3 CH 3 H H 0 Viscous oil 13.035 CH 3 CH 3 CH 3 H CH 3 013.036 CH 3 CH 3 CH 3 H CF 3 013.037 CH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 013.038 CH 3 CH 3 CH 3 H H 1 Amorphous Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.039 CH 3 CH 3 CH 3 H CH 3 113.040 CH 3 CH 3 CH 3 H CF 3 113.041 CH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 113.042 CH 3 CH 3 CH 3 H H 2 Resin 13.043 CH 3 CH 3 CH 3 H CH 3 213.044 CH 3 CH 3 CH 3 H CF 3 213.045 CH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 213.046 CH 3 CH 3 CH 3 CH 3 H 013.047 CH 3 CH 3 CH 3 CH 3 CH 3 013.048 CH 3 CH 3 CH 3 CH 3 CF 3 013.049 CH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 013.050 CH 3 CH 3 CH 3 CH 3 H 113.051 CH 3 CH 3 CH 3 CH 3 CH 3 113.052 CH 3 CH 3 CH 3 CH 3 CF 3 113.053 CH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 113.054 CH 3 CH 3 CH 3 CH 3 H 213.055 CH 3 CH 3 CH 3 CH 3 CH 3 213.056 CH 3 CH 3 CH 3 CH 3 CF 3 213.057 CH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 213.058 SCH 3 H CH 3 H H 0 125-128 ℃13.059 SO 2 CH 3 H CH 3 H H 0 Viscous oil 13.060 SCH 3 H CH 3 H CH 3 013.061 SCH 3 H CH 3 H CF 3 013.062 SCH 3 H CH 3 H CO 2 CH 2 H 3 013.063 SCH 3 H CH 3 H H 113.064 SCH 3 H CH 3 H CH 3 113.065 SCH 3 H CH 3 H CF 3 113.066 SCH 3 H CH 3 H CO 2 CH 2 CH 3 113.067 SCH 3 H CH 3 H H 213.068 SCH 3 H CH 3 H CH 3 213.069 SCH 3 H CH 3 H CF 3 213.070 SCH 3 H CH 3 H CO 2 CH 2 CH 3 2 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.071 SCH 3 CH 3 CH 3 H H 0 111-113℃ 13.072 SCH 3 CH 3 CH 3 H CH 3 013.073 SCH 3 CH 3 CH 3 H CF 3 013.074 SCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 013.075 SCH 3 CH 3 CH 3 H H 113.076 SCH 3 CH 3 CH 3 H CH 3 113.077 SCH 3 CH 3 CH 3 H CF 3 113.078 SCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 113.079 SCH 3 CH 3 CH 3 H H 2 Resin 13.080 SO 2 CH 3 CH 3 CH 3 H H 2 244-246 ℃13.081 SCH 3 CH 3 CH 3 H CH 3 213.082 SCH 3 CH 3 CH 3 H CF 3 2 viscous oil (E isomer) 13.083 SCH 3 CH 3 CH 3 H CF 3 2 viscous oil (Z isomer )13.084 SCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 213.085 SCH 3 H CH 3 CH 3 H 013.086 SCH 3 H CH 3 CH 3 CH 3 013.087 SCH 3 H CH 3 CH 3 CF 3 013.088 SCH 3 H CH 3 CH 3 CO 2 CH 2 CH 3 013.089 SCH 3 H CH 3 CH 3 H 113.090 SCH 3 H CH 3 CH 3 CH 3 113.091 SCH 3 H CH 3 CH 3 CF 3 113.092 SCH 3 H CH 3 CH 3 CO 2 CH 2 CH 3 113.093 SCH 3 H CH 3 CH 3 H 213.094 SCH 3 H CH 3 CH 3 CH 3 213.095 SCH 3 H CH 3 CH 3 CF 3 213.096 SCH 3 H CH 3 CH 3 CO 2 CH 2 CH 3 213.097 SCH 3 CH 3 CH 3 CH 3 H 013.098 SCH 3 CH 3 CH 3 CH 3 CH 3 013.099 SCH 3 CH 3 CH 3 CH 3 CF 3 013.100 SCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 013.101 SCH 3 CH 3 CH 3 CH 3 H 113.102 SCH 3 CH 3 CH 3 CH 3 CH 3 1 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.103 SCH 3 CH 3 CH 3 CH 3 CF 3 113.104 SCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 113.105 SCH 3 CH 3 CH 3 CH 3 H 213.106 SCH 3 CH 3 CH 3 CH 3 CH 3 213.107 SCH 3 CH 3 CH 3 CH 3 CF 3 213.108 SCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 213.109 SCH 3 SCH 3 H H H 013.110 SCH 3 SCH 3 H H CH 3 013.111 SCH 3 SCH 3 H H CF 3 013.112 SCH 3 SCH 3 H H CO 2 CH 2 CH 3 013.113 SCH 3 SCH 1 H H HCH 113.114 3 1 SCH H 3 S SCH 3 SCH 3 H H CF 3 113.116 SCH 3 SCH 3 H H CO 2 CH 2 CH 3 113.117 SCH 3 SCH 3 H H H 213.118 SCH 3 SCH 3 H H CH 3 213.119 SCH 3 SCH 3 H H CF 3 213.120 SCH 3 SCH 2 H CH 2 CH 3 213.121 SCH 3 SCH 3 CH 3 CH 3 H 013.122 SCH 3 SCH 3 CH 3 CH 3 CH 3 013.123 SCH 3 SCH 3 CH 3 CH 3 CF 3 013.124 SCH 3 SCH 3 CH 3 CH 3 CO 2 CH 2 CH 3 013.125 SCH 3 SCH 3 CH 3 CH 3 H 113.126 SCH 3 SCH 3 CH 3 CH 3 CH 3 113.127 SCH 3 SCH 3 CH 3 CH 3 CF 3 113.128 SCH 3 SCH 3 CH 3 CH 3 CO 2 CH 2 CH 3 113.329 SCH SCH 3 CH 3 CH 3 H 2 128-130°C (meso form) 13.130 SCH 3 SCH 3 CH 3 CH 3 H 2 189-192°C (E isomer) 13.131 SCH 3 SCH 3 CH 3 CH 3 CH 3 213.132 SCH 3 SCH 3 CH 3 CH 3 CF 3 213.133 SCH 3 SCH 3 CH 3 CH 3 CO 2 CH 2 CH 3 213.134 OCH 3 H H H H 0 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.135 OCH 3 H H H CH 3 013.136 OCH H H CF 3 013.137 OCH 3 H H CO 2 CH 2 CH 3 013.138 OCH 3 H H H 113.139 OCH 3 H H CH 3 113.140 OCH 3 H H CF 3 113.141 OCH 3 H H CH 2 CH 3 113.142 OCH 3 H H H H 213.14333.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.1433.143.13.143.13.143.13.143.13.143.13.143 . 3 H H H CH 3 213.144 OCH 3 H H H CF 3 213.145 OCH 3 H H H CO 2 CH 2 CH 3 213.146 OCH 3 H CH 3 H H 013.147 OCH 3 H CH 3 H CH 3 013.148 OCH 3 H CH 3 HCH CF 3 3 H CH 3 013.149 O 3 H CO 2 CH 2 CH 3 013.150 OCH 3 H CH 3 H H 113.151 OCH 3 H CH 3 H CH 3 113.152 OCH 3 H CH 3 H CF 3 113.153 OCH 3 H CH 3 H CO 2 CH 2 CH 3 113.154 OCH 3 H CH 3 H H 213.155 OCH 3 H CH 3 H CH 3 213.156 OCH 3 H CH 3 H CF 3 213.157 OCH 3 H CH 3 H CO 2 CH 2 CH 3 213.158 OCH 3 CH 3 CH 3 H H 0 Resin (E isomer) 13.159 OCH 3 CH 3 CH 3 H H 0 104-105° C (Z isomer) 13.160 OCH 3 CH 3 CH 3 H CH 3 013.161 OCH 3 CH 3 CH 3 H CF 3 013.162 OCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 013.163 OCH 3 CH 3 CH 3 H H 113.164 OCH 3 CH 3 CH 3 H CH 3 113.165 OCH 3 CH 3 CH 3 H CF 3 113.166 OCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 1 compound number R 6 R 6 R 7 R 7 R 18 n Physical data 13.167 OCH 3 CH 3 CH 3 H H 2 Resin (Z isomer) 13.168 OCH 3 CH 3 CH 3 H H 2 Resin (E isomer) 13.169 OCH 3 CH 3 CH 3 H CH 3 213.170 OCH 3 CH 3 CH 3 H CF 3 213.171 OCH 3 CH 3 CH 3 H CO 2 CH 2 CH 3 213.172 OCH 3 CH 3 CH 3 CH 3 H 013.173 OCH 3 CH 3 CH 3 CH 3 CH 3 013.174 OCH 3 CH 3 CH 3 CH 3 CF 3 013.175 OCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 013.176 OCH 3 CH 3 CH 3 CH 3 H 113.177 OCH 3 CH 3 CH 3 CH 3 CH 3 113.178 OCH 3 CH 3 CH 3 CH 3 CF 3 113.179 OCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 113.180 OCH 3 CH 3 CH 3 CH 3 H 213.181 OCH 3 CH 3 CH 3 CH 3 CH 3 213.182 OCH 3 CH 3 CH 3 CH 3 CF 3 213.183 OCH 3 CH 3 CH 3 CH 3 CO 2 CH 2 CH 3 213.184 OCH 3 H OCH 3 H H 013.185 OCH 3 H OCH 3 H CH 3 013.186 OCH 3 H OCH 3 H CF 3 013.187 OCH 3 H OCH 3 H CO 2 CH 2 CH 3 013.188 OCH 3 H OCH 3 H H 113.189 OCH 3 H OCH 3 H CH 3 113.190 OCH 3 H OCH 3 H CF 3 113.191 OCH 3 H OCH 3 H CO 2 CH 2 CH 3 113.192 OCH 3 H OCH 3 H H 213.193 OCH 3 H OCH 3 H CH 3 213.194 OCH 3 H OCH 3 H CF 3 213.195 OCH 3 H OCH 3 H CO 2 CH 2 CH 3 213.196 OCH 3 CH 3 OCH 3 CH 3 H 013.197 OCH 3 CH 3 OCH 3 CH 3 CH 3 013.198 OCH 3 CH 3 OCH 3 CH 3 CF 3 0 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.199 OCH 3 CH 3 OCH 3 CH 3 CO 2 CH 2 CH 3 013.200 OCH 3 CH 3 OCH 3 CH 3 H 113.201 OCH 3 CH 3 OCH 3 CH 3 CH 3 113.202 OCH 3 CH 3 OCH 3 CH 3 CF 3 113.203 OCH 3 CH 3 OCH 3 CH 3 CO 2 CH 2 CH 3 113.204 OCH 3 CH 3 OCH 3 CH Amorphous _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ 13.209 SCH 3 CH 3 OCH 3 H CH 3 013.210 SCH 3 CH 3 OCH 3 H CF 3 013.211 SCH 3 CH 3 OCH 3 H CO 2 CH 2 CH 3 013.212 SCH 3 CH 3 OCH 3 H H 113.213 SCH 3 CH 3 OCH 3 H CH 3 113.214 SCH 3 CH 3 OCH 3 H CF 3 113.215 SCH 3 CH 3 OCH 3 H CO 2 CH 2 CH 3 113.216 SCH 3 CH 3 OCH 3 H H 2 166-168°C 13.217 SCH 3 CH 3 OCH 3 H CH 3 213.218 SCH 3 CH 3 OCH 3 H CF 3 213.219 SCH 3 CH 3 OCH 3 H CO 2 CH 2 CH 3 213.220 SCH 3 CH 3 OCH 3 CH 3 H 013.221 SCH 3 CH 3 OCH 3 CH 3 CH 3 013.222 SCH 3 CH 3 OCH 3 CH 3 CF 3 013.223 SCH 3 CH 3 OCH 3 CH 3 CO 2 CH 2 CH 3 013.224 SCH 3 CH 3 OCH 3 CH 3 H 113.225 SCH 3 CH 3 OCH 3 CH 3 CH 3 113.226 SCH 3 CH 3 OCH 3 CH 3 CF 3 113.227 SCH 3 CH 3 OCH 3 CH 3 CO 2 CH 2 CH 3 113.228 SCH 3 CH 3 OCH 3 CH 3 H 213.229 SCH 3 CH 3 OCH 3 CH 3 CH 3 213.230 SCH 3 CH 3 OCH 3 CH 3 CF 3 2 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.231 SCH 3 CH 3 OCH 3 CH 3 CO 2 CH 2 CH 3 213.232 CH 3 H CH 3 CH 2 CH =CH 2 H 013.233 CH 3 H CH 3 CH 2 CH=CH 2 CH 3 013.234 CH 3 H CH 3 CH 2 CH=CH 2 CF 3 013.235 CH 3 H CH 3 CH 2 CH=CH 2 CO 2 CH 2 CH 3 013.236 CH 3 H CH 3 CH 2 CH=CH 2 H 113.237 CH 3 H CH 3 CH 2 CH=CH 2 CH 3 113.238 CH 3 H CH 3 CH 2 CH=CH 2 CF 3 113.239 CH 3 H CH 3 CH 2 CH=CH 2 CO 2 CH 2 CH 3 113.240 CH 3 H CH 3 CH 2 CH=CH 2 H 2 Viscous oil 13.241 CH 3 H CH 3 CH 2 CH=CH 2 CH 3 213.242 CH 3 H CH 3 CH 2 CH =CH 2 CF 3 213.243 CH 3 H CH 3 CH 2 CCH CO 2 CH 2 CH 3 213.244 CH 3 H CH 3 CH 2 CCH H 013.245 CH 3 H CH 3 CH 2 CCH CH 3 013.246 CH 3 H CH 3 CH 2 CCH CF 3 013.247 CH 3 H CH 3 CH 2 CCH CO 2 CH 2 CH 3 013.248 CH 3 H CH 3 CH 2 CCH H 13.249 CH 3 H CH 3 CH 2 CCH CH 3 113.250 CH 3 H CH 3 CH 2 CCH CF 3 113.251 CH 3 H CH 3 CH 2 CCH CO 2 CH 2 CH 3 113.252 CH 3 H CH 3 CH 2 CCH H 2 Viscous oil 13.253 CH 3 H CH 3 CH 2 CCH CH 3 213.254 CH 3 H CH 3 CH 2 CCH CF 3 213.255 CH 3 H CH 3 CH 2 CCH CO 2 CH 2 CH 3 213.256 CH 3 CH 3 CH 3 CH 2 CH=CH 2 H 013.257 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CH 3 013.258 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CF 3 013.259 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CO 2 CH 2 CH 3 0 Compound No. R 6 R 6 R 7 R 7 R 18 n Physical Data 13.260 CH 3 CH 3 CH 3 CH 2 CH=CH 2 H 113.261 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CH 3 113.262 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CF 3 113.263 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CO 2 CH 2 CH 3 113.264 CH 3 CH 3 CH 3 CH 2 CH=CH 2 H 213.265 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CH 3 213.266 CH 3 CH 3 CH 3 CH 2 CH=CH 2 CF 3 213.267 CH 3 CH 3 CH 3 CH 2 CCH CO 2 CH 2 CH 3 213.268 CH 3 CH 3 CH 3 CH 2 CCH H 013.269 CH 3 CH 3 CH 3 CH 2 CCH CH 3 013.270 CH 3 CH 3 CH 3 CH 2 CCH CF 3 013.271 CH 3 CH 3 CH 3 CH 2 CCH CO 2 CH 2 CH 3 013.272 CH 3 CH 3 CH 3 CH 2 CCH H 113.273 CH 3 CH 3 CH 3 CH 2 CCH CH 3 113.274 CH 3 CH 3 CH 3 CH 2 CCH CF 3 113.275 CH 3 CH 3 CH 3 CH 2 CCH CO 2 CH 2 CH 3 113.276 CH 3 CH 3 CH 3 CH 2 CCH H 213.277 CH 3 CH 3 CH 3 CH 2 CCH CH 3 213.278 CH 3 CH 3 CH 3 CH 2 CCH CF 3 213.279 CH 3 CH 3 CH 3 CH 2 CCH CO 2 CH 2 CH 3 2

表C：在以上表1-6和A以及8-11和B中所制备的化合物的物理化学数据。小数点之前的数表示表的号码，例如1.027表示在表1中表A的化合物027，和11.027表示在表11中表C的化合物027。 化合物号 物理化学数据  1.0011.0021.003  m.p.215-218℃m.p.180℃m.p.204-206℃ 化合物号 物理化学数据  1.0051.0081.0161.0271.0291.0301.0311.0331.0342.0012.0022.0032.0052.0082.0272.0282.0292.0302.0332.0342.8073.0273.0293.0335.0276.0056.0276.0299.0019.02710.00110.003  m.p.225-226℃m.p.213-216℃m.p.194-196℃m.p.223-225℃m.p.220-230℃m.p.222℃m.p.263-264℃m.p.187-189℃m.p.220-221℃m.p.123-126℃m.p.127-129℃m.p.112-114℃m.p.133-134℃m.p.173-174℃m.p.170-172℃m.p.168-171℃m.p.173-174℃m.p.252℃m.p.132-135℃m.p.206℃m.p.134-135℃m.p.183-184℃m.p.185-186℃m.p.141-144℃树脂树脂m.p.194-195℃m.p.189-190℃m.p.129-130℃m.p.178-180℃m.p.191-193℃m.p.192-193℃ 化合物号 物理化学数据  10.01610.02710.02910.03311.00111.02711.04011.066  m.p.199-200℃m.p.230-233℃m.p.191-192℃m.p.222-224℃m.p.185-188℃m.p.216-218℃m.p.117-120℃m.p.213-215℃ Table C: Physicochemical data for the compounds prepared in Tables 1-6 and A and 8-11 and B above. The number before the decimal point indicates the number of the table, for example 1.027 indicates the compound 027 of Table A in Table 1, and 11.027 indicates the compound 027 of Table C in Table 11. Compound No. Physicochemical data 1.0011.0021.003 mp215-218℃mp180℃mp204-206℃ Compound No. Physicochemical data 1.0051.0081.0161.0271.0291.0301.0311.0331.0342.0012.0022.0032.0052.0082.0272.0282.0292.0302.0332.0342.8073.0273.0293.0335.0276.0056.0276.0299.0019.02710.00110.003 mp225-226℃mp213-216℃mp194-196℃mp223-225℃mp220-230℃mp222℃mp263-264℃mp187-189℃mp220-221℃mp123-126℃mp127-129℃mp112-114℃mp133-134℃ mp173-174℃mp170-172℃mp168-171℃mp173-174℃mp252℃mp132-135℃mp206℃mp134-135℃mp183-184℃mp185-186℃mp141-144℃resin resin mp194-195℃mp189-190℃ mp129-130℃mp178-180℃mp191-193℃mp192-193℃ Compound No. Physicochemical data 10.01610.02710.02910.03311.00111.02711.04011.066 mp199-200℃mp230-233℃mp191-192℃mp222-224℃mp185-188℃mp216-218℃mp117-120℃mp213-215℃

通式I化合物的特定配方的实例，如乳化浓缩物，溶液，可湿性粉剂，包衣粒料，挤出粒料，粉剂和悬浮浓缩液，描述在WO97/34485的第9-13页。Examples of specific formulations of compounds of general formula I, such as emulsified concentrates, solutions, wettable powders, coated granules, extruded granules, dusts and suspension concentrates, are described on pages 9-13 of WO 97/34485.

生物实施例：Biological example:

实施例B1：植物出芽前的除草作用(出芽前作用)Example B1: Herbicidal action on plants before emergence (preemergence action)

在塑料盆中的标准土壤中种下单子叶和双子叶试验植物。在播种之后立即以对应于2000g活性成分/ha(500升水/ha)的浓度通过喷雾来施用试验化合物，试验化合物的施用形式是从例如WO97/34485中描述的25％可湿性粉剂(实施例F3，b)制得的水悬浮液或乳液形式，或乳液形式(从例如WO97/34485中描述的25％可乳化浓缩物(实施例F1，c)制得)。试验植物然后在最佳条件下在温室中生长。在试验经过3周后，根据9个判分等级(1＝完全损害，9＝没有作用)来评价试验结果。1-4(尤其1-3)的判分等级表示良好至非常良好的除草作用。Monocotyledonous and dicotyledonous test plants were grown in standard soil in plastic pots. Immediately after sowing, the test compound is applied by spraying at a concentration corresponding to 2000 g active ingredient/ha (500 liters of water/ha) in the form of a 25% wettable powder as described in WO 97/34485 (Example F3 , b) prepared in the form of an aqueous suspension or emulsion, or in the form of an emulsion (prepared, for example, from a 25% emulsifiable concentrate as described in WO 97/34485 (Example F1, c)). The test plants are then grown in a greenhouse under optimal conditions. After 3 weeks of testing, the test results were evaluated according to a 9-point scale (1=complete impairment, 9=no effect). A rating of 1-4 (especially 1-3) indicates good to very good herbicidal action.

试验植物：莎草属，芥属，茄属Test plants: Cyperus, Brassica, Solanum

根据本发明的化合物显示出良好的除草作用。The compounds according to the invention show good herbicidal action.

在表B1中给出了通式I化合物的良好除草活性的实例。表B1：出芽前作用浓度试验植物    莎草属    芥属    茄属    浓度Examples of good herbicidal activity of compounds of the general formula I are given in Table B1. Table B1: Pre-emergent concentration test plants Cyperus Brassica Solanum Concentration

                                [ga.i./ha]化合物号ld No.2.001        6        2        2      20002.003        1        1        1      20002.027        3        2        2      20002.029        1        1        1      20002.034        3        5        3      20002.807        2        2        5      20003.027        3        1        1      20006.029        3        2        2      20009.001        3        2        1      200010.001       4        5        3      200010.027       3        3        2      200011.027       4        4        1      200012.012       3        7        3      200013.007       2        2        2      200013.022       3        2        2      200013.030       4        4        2      200013.038       3        2        2      2000[GA.I./HA] compound LD No.2.001 6 2 20002.003 1 10002.027 3 2 20002.029 1 10002.034 3 3 3 20002.807 2 5 20003.027 3 1 20006.029 3 2 20009.001 3 2 1000.001 20000.001 4 5 3 200010.027 3 3 2 200011.027 4 4 1 200012.012 3 7 300013.007 2 2 200013.022 3 2 200013.030 4 4 2 200013.038 3 2 2 2000

当根据例如WO97/34485中描述的实施例F2-F8来配制通式I的化合物时，获得了同样的结果。The same results were obtained when the compounds of general formula I were formulated according to examples F2-F8 described eg in WO97/34485.

实施例B2：出芽后除草作用Example B2: Post-emergence herbicidal action

在温室中，在塑料盆中的标准土壤中种下单子叶和双子叶试验植物，在4至6叶阶段，以对应于2000g活性成分/ha(500升水/ha)的浓度用通式I试验化合物的水悬浮液或乳液(从例如WO97/34485中描述的25％可湿性粉剂(实施例F3，b)制得)或用该化合物的乳液形式(从例如WO97/34485中描述的25％可乳化浓缩物(实施例F1，c)制得)进行喷雾。试验植物然后在最佳条件下在温室中生长。在试验经过18天后，根据9个判分等级(1＝完全损害，9＝没有作用)来评价试验结果。1-4(尤其1-3)的判分等级表示良好至非常良好的除草作用。Monocotyledonous and dicotyledonous test plants were planted in standard soil in plastic pots in the greenhouse and were tested with the general formula I at a concentration corresponding to 2000 g active ingredient/ha (500 liters of water/ha) at the 4 to 6 leaf stage An aqueous suspension or emulsion of the compound (prepared from, for example, the 25% wettable powder described in WO 97/34485 (Example F3, b)) or an emulsion form of the compound (from the 25% wettable powder described in, for example, WO 97/34485) The emulsified concentrate (produced in Example F1, c)) was sprayed. The test plants are then grown in a greenhouse under optimal conditions. After 18 days of the test, the test results were evaluated according to a 9-point scale (1=complete damage, 9=no effect). A rating of 1-4 (especially 1-3) indicates good to very good herbicidal action.

试验植物：狗尾草属，芥属，茄属，繁缕属Test plants: Setaria, Brassica, Solanum, Chickweed

在这些试验中，通式I的化合物同样显示出强力除草作用。In these tests, the compounds of the general formula I likewise exhibit potent herbicidal action.

在表B2中给出了通式I化合物的良好除草活性的实例。Examples of good herbicidal activity of compounds of the general formula I are given in Table B2.

表B2：出芽后作用Table B2: Postemergence effects

试验植物    狗尾草属  芥属    茄属  繁缕属  浓度Test Plant Setaria Mustard Solanum Chickweed Concentration

                                         [g a.i/ha][g a.i/ha]

化合物号Compound No.

2.001          3       1        2     4     20002.001 3 1 2 4 2000

2.002          6       2        1     4     20002.002 6 2 1 4 2000

2.003          4       2        2     3     20002.003 4 2 2 3 2000

2.005          4       2        2     3     20002.005 4 2 2 3 2000

2.008          5       2        2     2     20002.008 5 2 2 2 2 2000

2.027          3       1        2     3     20002.027 3 1 2 3 2000

2.028          3       2        2     3     20002.028 3 2 2 2 3 2000

2.029          5       2        2     2     20002.029 5 2 2 2 2 2000

2.030          5       2        2     2     20002.030 5 2 2 2 2 2000

2.034          3       2        2     3     20002.034 3 2 2 2 3 2000

2.807          3       2        1     2     20002.807 3 2 1 2 2000

3.027          4       1        1     4     20003.027 4 1 1 1 4 2000

3.029          5       2        2     2     20003.029 5 2 2 2 2 2000

5.027          3       2        1     2     20005.027 3 2 1 2 2000

6.005          2       2        2     2     20006.005 2 2 2 2 2 2000

6.027          5       1        4     3     20006.027 5 1 1 4 3 2000

6.029          7       1        1     2     20006.029 7 1 1 2 2000

7.027          8       2        2     4     20007.027 8 2 2 4 2000

9.001          4       1        1     3     20009.001 4 1 1 1 3 2000

9.027          3       2        2     4     20009.027 3 2 2 2 4 2000

10.001      3       1        1     3     2000 10.003    3    1    2    3    200010.016    3    2    3    3    200010.027    3    1    2    4    200010.029    3    3    2    3    200011.001    2    1    2    3    200011.027    2    2    2    2    200011.040    1    2    2    2    200011.066    2    1    2    2    200012.012    3    1    1    3    200013.001    4    1    1    3    200013.007    3    1    2    2    200013.022    5    1    1    2    200013.030    5    1    1    2    200013.034    3    1    1    3    200013.038    3    1    1    2    200013.042    4    1    1    2    200013.058    6    2    2    3    200013.059    7    3    2    4    200013.071    7    2    1    2    200013.079    4    1    1    3    200013.080    6    1    1    2    200013.158    2    1    1    2    200013.159    3    3    3    3    200013.167    2    1    1    2    200013.168    2    2    2    2    200013.216    6    2    4    2    200013.240    3    1    2    3    200013.252    3    3    2    3    200010.001 3 1 1 3 2000 10.003 3 1 2 3 200010.016 3 2 3 300010.027 3 1 4 200010.029 3 3 200011.001 2 1 2 3 200011.027 2 2 2 200011.040 1 2 2 2 2 2 2 200012.012 3 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 3 200013.001 4 1 1 3 200013.007 3 1 2 2 200013.022 5 1 1 200013.030 5 1 200013.034 3 1 3 200013.038 3 1 200013.042 4 1 2 200013.058 6 2 3 200013.071 7 2 1 1 2 200013.079 4 1 1 3 200013.080 6 1 2 200013.158 2 1 2 200013.159 3 3 3 300013.167 2 1 2 200013.168 2 2 2 200013.216 6 2 200013.240 3 100013.252 3 3 3 3 2 200000

当根据例如WO97/34485中描述的实施例F2-F8来配制通式I的化合物时，获得了同样的结果。The same results were obtained when the compounds of general formula I were formulated according to examples F2-F8 described eg in WO97/34485.

Claims (9)

1st, a kind of compounds of formula I：
Figure A9880674200021
Wherein R1It is C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxy -C1-C4Alkyl, C1-C4Alkoxy carbonyl, cyano group, cyano group C1-C4Alkyl, hydroxyl-C1-C4Alkyl, amino-C1-C4Alkyl, CHO, C1-C4Alkyl-ON=CH, C2-C6Alkenyl, C1-C4Alkoxy carbonyl-C2-C6Alkenyl or group-CH (OR20)OR21；
R20And R21It is C independently of each other1-C4Alkyl；Or R20And R21It is-(CH together2)n1-；n1It is 2,3 or 4；R2It is hydrogen or C1-C4Alkyl；R3And R4It is hydrogen, C independently of each other1-C4Alkyl or halogen；N is 0,1 or 2；R5It is C1-C4Alkyl, C1-C4Haloalkyl, C2-C6Alkenyl, C2-C6Alkynyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-S (O)n2, (C1-C4Alkyl)2NS(O)2, C1-C4Alkyl-S (O)2O, halogen, nitro or cyano group；n2It is 0,1 or 2；Q is OH, halogen or group
Figure A9880674200022
R6And R7It is hydrogen, OH, C independently of each other1-C4Alkyl, C2-C6Alkenyl, C2-C6Alkynyl, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Alkyl-NHS (O)2, phenyl or by C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, amino, C1-C4Alkyl amino, two-C1-C4Alkyl amino, C1-C4Alkyl-S (O)n2, C1-C4Alkyl-S (O)2O, C1-C4Haloalkyl-S (O)n2, C1-C4Haloalkyl-S (O)2O, C1-C4Alkyl-S (O)2NH, C1-C4Alkyl-S (O)2N(C1-C4Alkyl), halogen, nitro, the phenyl that COOH or cyano group replace；Or R6And R7It is C independently of each other1-C4Haloalkyl ,-NH-C1-C4Alkyl ,-N (C1-C4Alkyl)2, C1-C6Alkoxy, cyano group, nitro or halogen；Or adjacent R6And R7It is-(CH together2)n3-；N3 is 2,3,4,5 or 6；W is oxygen, sulphur ,-C (R18)2- or-N (R22)-；n6It is O or 1, or when W is-C (R18)2- when, n6Can be 2 or 3 in addition；Each R18It is independently hydrogen, C1-C4Alkyl, C1-C4Haloalkyl or C1-C4Alkoxy carbonyl；Or work as n6When being 1, R18With adjacent substituents R7In a formation singly-bound, and remaining paired R6And R7It is the group beyond hydrogen；R22It is hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl；R8It is OH, C1-C4Alkoxy, C1-C4Alkyl carbonyl epoxide, C1-C4Alkoxy-carbonyl oxy, R23R24N-C (O) O, thiophenyl, C1-C4Alkylthio group, C1-C4Alkyl-S (O)2O, (C1-C4Alkoxy)2P (O) O, C1-C4Alkyl (C1-C4Alkoxy) P (O) O, H (C1-C4Alkoxy) P (O) O or benzoyloxy；R23And R24It is hydrogen or C independently of each other1-C4Alkyl；Y is oxygen, sulphur or-(CH2)n5-；n5It is 0,1,2,3 or 4；R9It is hydrogen, C1-C6Alkyl, C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, (C1-C4Alkyl) NHCO or (C1-C4Alkyl)2NCO；R10, R11And R12It is hydrogen, C independently of one another1-C4Alkyl, C1-C4Alkoxy carbonyl, phenyl or by C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-carbonyl, C1-C4Alkoxy carbonyl, amino, C1-C4Alkyl amino, two-C1-C4Alkyl amino, C1-C4Alkyl-S (O)n2, C1-C4Alkyl-S (O)2O, C1-C4Haloalkyl-S (O)n2, C1-C4Haloalkyl-S (O)2O, C1-C4Alkyl-S (O)2NH, C1-C4Alkyl-S (O)2N(C1-C4Alkyl), halogen, nitro, the phenyl that COOH or cyano group replace；R13It is hydrogen；Halogen；C1-C4Alkyl；By unsubstituted or R17The C that substituted phenyl is replaced1-C4Alkyl；C1-C4Haloalkyl；C2-C6Alkenyl；By unsubstituted or R17The C that the phenyl of-substitution is replaced2-C6Alkenyl；C2-C6Alkynyl；By unsubstituted or R17The C that substituted phenyl is replaced2-C6Alkynyl；C3-C6Halogenated alkenyl；C3-C6Halo alkynyl；C3-C6Cycloalkyl；By halogen, R15Or COOR16Substituted C3-C6Cycloalkyl；COOR16；COR15；Cyano group；Nitro；CONH2；(C1-C4Alkyl) NHCO；(C1-C4Alkyl)2NCO；(C1-C4Haloalkyl) NHCO；(C1-C4Haloalkyl)2NCO；C1-C4Alkyl S (O)n2；By unsubstituted or R17The C that the phenyl of-substitution is replaced1-C4Alkyl-S (O)n2；C1-C4Alkoxy -C2-C6Alkyl-S (O)n2；C2-C6Alkenyl-S (O)n2；By unsubstituted or R17The C that the phenyl of-substitution is replaced2-C6Alkenyl-S (O)n2；C2-C6Alkynyl-S (O)n2；Or by unsubstituted or R17The C that the phenyl of-substitution is replaced2-C6Alkynyl-S (O)n2；R15It is C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, phenyl or R17The phenyl of-substitution；R16It is hydrogen, C1-C4Alkyl or C1-C4Haloalkyl；R17It is halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, C1-C4Alkoxy -C1-C4Alkyl, C1-C4Alkoxy -C3-C6Alkenyl, C1-C4Alkoxy -C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Halo alkoxy carbonyl, C1-C4Alkyl S (O)n2, C1-C4Haloalkyl-S (O)n2, phenyl-S (O)n2；By halogen on phenyl ring, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl-S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-S (O)2O or C1-C4Haloalkyl-S (O)2Phenyl-the S (O) of O substitutionsn2；C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkyl-S (O)2NH, C1-C4Alkyl-S (O)2N(C1-C4Alkyl), C1-C4Haloalkyl-S (O)2NH, C1-C4Haloalkyl-S (O)2N(C1-C4Alkyl), NH2S(O)2, (C1-C4Alkyl) NHS (O)2, (C1-C4Alkyl)2NS(O)2, CONH2, (C1-C4Alkyl) NHCO, (C1-C4Alkyl)2NCO, NH2CS, (C1-C4Alkyl) NHCS, (C1-C4Alkyl)2NCS, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C3-C6Alkenyl oxy, C3-C6Alkynyl epoxide, C1-C4Alkyl-S (O)2O, C1-C4Haloalkyl-S (O)2O, phenyl-S (O)2O or on phenyl ring by halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl S (O)2O or C1-C4Haloalkyl-S (O)2The phenyl S (O) of O substitutions2O；And R14It is C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, C3-C6Cycloalkyl or the C by following substituent group3-C6Cycloalkyl：Halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, phenyl or by halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl-S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-S (O)2O or C1-C4Haloalkyl S (O)2The phenyl of O substitutions, and acceptable salt and its stereoisomer on the agriculture chemistry of compound of Formula I.
2nd, compound according to claim 1, wherein R1It is C1-C4Alkyl, C1-C4Haloalkyl, C1-C4Alkoxy -C1-C4Alkyl, C1-C4Alkoxy carbonyl, cyano group, cyano group-C1-C4Alkyl, CHO, C1-C4Alkyl-ON=CH, C2-C6Alkenyl, C1-C4Alkoxy carbonyl-C2-C6Alkenyl or group-CH (OR20)OR21；W is oxygen, sulphur ,-C (R18)2- or-N (R22)-；Each R18It is independently hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl；And R22It is hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl.
3rd, a kind of method for preparing compounds of formula I
Figure A9880674200051
Wherein R1-R5With n as defined in claim 1, Q is group
Figure A9880674200052
Figure A9880674200053
R8It is OH；And R6, R7, R9, R10, W, n6With Y as defined in claim 1, this method includes a) allowing compounds of formula III
Figure A9880674200061
Wherein R1-R5It is as defined above leaving group with X with n, is reacted in the presence of a base with compounds of formula IV in inert organic solvents
Figure A9880674200062
Wherein Z1It is C (R6)R7, Z2It is (W)n6, Z3It is C (R6)R7And n4It is O (=group Q1)；Z1It is CH, Z2It is oxygen, sulphur or-(CH2)n5- (=Y), Z3It is CH and n4It is 2 (=group Q2)；Z1It is CH2, Z2It is CHNHR9, Z3It is CH2And n4It is O (=group Q3)；Or Z1It is NR10, Z2It is oxygen, Z3It is C (R6)R7And n4It is O (=group Q4), and R6, R7, R9, R10, W, n6And n5As defined in claim 1, formula Ic compound is formed：
Figure A9880674200063
With and then by the compound isomerizate；Or d) allow formula Id compound
Figure A9880674200064
Wherein R1-R5With n as defined above, with compounds of formula IV,
Figure A9880674200065
Wherein Z1, Z2, Z3And n4As defined above, reacted in inert organic solvents in the presence of alkali and coupling agent, form formula Ic compound：
Figure A9880674200071
Then, by the compound isomerizate.
4th, a kind of compounds of formula V
Figure A9880674200072
Wherein R1-R5, R14It is as defined in claim 1 with n.
5th, a kind of compounds of formula VII
Figure A9880674200073
Wherein R1-R5, R14It is as defined in claim 1 with n；R25It is C1-C4Alkyl, by unsubstituted or R17The C that substituted phenyl is replaced1-C4Alkyl, C1-C4Alkoxy -C2-C6Alkyl, C2-C6Alkenyl, by unsubstituted or R17The C that substituted phenyl is replaced2-C6Alkenyl, C2-C6Alkynyl, by unsubstituted or R17The C that substituted phenyl is replaced2-C6Alkynyl；R17It is halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, C1-C4Alkoxy -C1-C4Alkyl, C1-C4Alkoxy -C3-C6Alkenyl, C1-C4Alkoxy -C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Halo alkoxy carbonyl, C1-C4Alkyl S (O)n2, C1-C4Haloalkyl-S (O)n2, phenyl-S (O)n2；By halogen on phenyl ring, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl-S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-S (O)2O or C1-C4Haloalkyl-S (O)2Phenyl-the S (O) of O substitutionsn2；C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkyl-S (O)2NH, C1-C4Alkyl-S (O)2N(C1-C4Alkyl), C1-C4Haloalkyl-S (O)2NH, C1-C4Haloalkyl-S (O)2N(C1-C4Alkyl), NH2S(O)2, (C1-C4Alkyl) NHS (O)2, (C1-C4Alkyl)2NS(O)2, CONH2, (C1-C4Alkyl) NHCO, (C1-C4Alkyl)2NCO, NH2CS, (C1-C4Alkyl) NHCS, (C1-C4Alkyl)2NCS, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C3-C6Alkenyl oxy, C3-C6Alkynyl epoxide, C1-C4Alkyl-S (O)2O, C1-C4Haloalkyl-S (O)2O, phenyl-S (O)2O or on phenyl ring by halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl S (O)2O or C1-C4Haloalkyl-S (O)2The phenyl S (O) of O substitutions2O；And n2It is 0,1 or 2.
6th, a kind of compounds of formula IX：
Figure A9880674200081
Wherein R1-R5, R14It is as defined in claim 1 with n；R13It is hydrogen, C1-C4Alkyl, by unsubstituted or R17The C that substituted phenyl is replaced1-C4Alkyl, C1-C4Haloalkyl, C2-C6Alkenyl, by unsubstituted or R17The C that the phenyl of-substitution is replaced2-C6Alkenyl, C2-C6Alkynyl, by unsubstituted or R17The C that substituted phenyl is replaced2-C6Alkynyl, C3-C6Halogenated alkenyl, C3-C6Halo alkynyl, C3-C6Cycloalkyl or by halogen, R15Or COOR16The C replaced3-C6Cycloalkyl；R17It is halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, C1-C4Alkoxy -C1-C4Alkyl, C1-C4Alkoxy -C3-C6Alkenyl, C1-C4Alkoxy -C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Halo alkoxy carbonyl, C1-C4Alkyl S (O)n2, C1-C4Haloalkyl-S (O)n2, phenyl-S (O)n2；By halogen on phenyl ring, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl-S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl-S (O)2O or C1-C4Haloalkyl-S (O)2Phenyl-the S (O) of O substitutionsn2；C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkyl-S (O)2NH, C1-C4Alkyl-S (O)2N(C1-C4Alkyl), C1-C4Haloalkyl-S (O)2NH, C1-C4Haloalkyl-S (O)2N(C1-C4Alkyl), NH2S(O)2, (C1-C4Alkyl) NHS (O)2, (C1-C4Alkyl)2NS(O)2, CONH2, (C1-C4Alkyl) NHCO, (C1-C4Alkyl)2NCO, NH2CS, (C1-C4Alkyl) NHCS, (C1-C4Alkyl)2NCS, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C3-C6Alkenyl oxy, C3-C6Alkynyl epoxide, C1-C4Alkyl-S (O)2O, C1-C4Haloalkyl-S (O)2O, phenyl-S (O)2O or on phenyl ring by halogen, C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl, cyano group, nitro, COOH, C1-C4Alkoxy carbonyl, C1-C4Alkyl-S (O)n2, C1-C4Haloalkyl S (O)n2, C1-C4Alkyl-carbonyl, two-C1-C4Alkyl amino, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkyl S (O)2O or C1-C4Haloalkyl-S (O)2The phenyl S (O) of O substitutions2O；And n2It is 0,1 or 2；R15It is C1-C4Alkyl, C1-C4Haloalkyl, C3-C6Alkenyl, C3-C6Halogenated alkenyl, C3-C6Alkynyl, C3-C6Halo alkynyl, phenyl or R17The phenyl of-substitution；R16It is hydrogen, C1-C4Alkyl or C1-C4Haloalkyl；And R27It is C1-C4Alkyl.
7th, a kind of weeding and plant growth composite inhibiting, compound of Formula I and inert carrier comprising weeding effective content.
8th, a kind of method for controlling undesired plant growth, wherein compounds of formula I or the composition including the compound are applied on the crop of useful plant with herbicidally effective amount or in it grows place.
9th, composition according to claim 7 is used for the purposes for controlling undesired plant growth.
CN 98806742 1997-08-20 1998-08-18 Benzothiophene derivatives used as herbicides Pending CN1261884A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1950/1997 1997-08-20
CH195097 1997-08-20

Publications (1)

Publication Number Publication Date
CN1261884A true CN1261884A (en) 2000-08-02

Family

ID=4222392

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 98806742 Pending CN1261884A (en) 1997-08-20 1998-08-18 Benzothiophene derivatives used as herbicides

Country Status (6)

Country Link
EP (1) EP1005467A1 (en)
CN (1) CN1261884A (en)
AU (1) AU732154B2 (en)
BR (1) BR9811314A (en)
CA (1) CA2291101A1 (en)
WO (1) WO1999009023A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112430228A (en) * 2020-11-25 2021-03-02 四川大学 Chiral 2, 3-dihydrobenzo [ b ] thiophene 1, 1-dioxide, derivative and preparation method

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU760018B2 (en) * 1998-10-06 2003-05-08 Idemitsu Kosan Co. Ltd Triketone derivative and herbicide
DE19935218A1 (en) 1999-07-27 2001-02-01 Aventis Cropscience Gmbh Isoxazolyl-substituted benzoylcyclohexanediones, process for their preparation and their use as herbicides and plant growth regulators
PL201229B1 (en) * 1999-09-08 2009-03-31 Aventis Cropscience Uk Ltd New herbicidal compositions
AU2001242451A1 (en) * 2000-03-09 2001-09-17 Syngenta Participations Ag Acylated phenyl or pyridine herbicides
US20040058957A1 (en) * 2000-12-21 2004-03-25 Seiji Tomita Benzothiophene derivatives and herbicidal compositions containing the same
WO2015000715A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
WO2023094304A1 (en) 2021-11-25 2023-06-01 Syngenta Crop Protection Ag Microbiocidal heterobiaryl amide derivatives

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5946272A (en) * 1982-09-09 1984-03-15 Nissan Chem Ind Ltd Pyrazole derivative, its preparation and selective herbicide containing said derivative
DE3862944D1 (en) * 1987-02-09 1991-07-04 Ciba Geigy Ag NEW CYCLOHEXANDIONE.
US5006150A (en) * 1987-06-05 1991-04-09 Sandoz Ltd. Substituted heterocyclohexane-3,5-diones
HU206242B (en) * 1988-04-18 1992-10-28 Sandoz Ag Herbicidal compositions comprising substituted benzoyl bicyclodione derivatives as active ingredient
CN1071091C (en) * 1994-08-01 2001-09-19 罗纳-普朗克农业有限公司 Novel herbicide composition
US5627131A (en) * 1995-01-09 1997-05-06 Zeneca Limited Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor
JPH11501009A (en) * 1995-02-24 1999-01-26 ビーエーエスエフ アクチェンゲゼルシャフト Isoxazolylbenzoyl derivative
DK0811007T3 (en) * 1995-02-24 2006-02-06 Basf Ag Pyrazol-4-yl benzoyl derivatives and their use as herbicides
AU6777896A (en) * 1995-08-25 1997-03-19 E.I. Du Pont De Nemours And Company Bicyclic herbicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112430228A (en) * 2020-11-25 2021-03-02 四川大学 Chiral 2, 3-dihydrobenzo [ b ] thiophene 1, 1-dioxide, derivative and preparation method
CN112430228B (en) * 2020-11-25 2021-09-07 四川大学 A kind of chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxide, derivative and preparation method

Also Published As

Publication number Publication date
AU9344198A (en) 1999-03-08
EP1005467A1 (en) 2000-06-07
CA2291101A1 (en) 1999-02-25
WO1999009023A1 (en) 1999-02-25
AU732154B2 (en) 2001-04-12
BR9811314A (en) 2000-08-29

Similar Documents

Publication Publication Date Title
CN1036305C (en) Herbicidal composition and its application
JP4965050B2 (en) Substituted pyridine herbicides
JP7515544B2 (en) Herbicidal 4-difluoromethylbenzoylamide
CN1076351C (en) Heterocyclic substituted benzene derivatives and herbicides
CN1170825C (en) isoxazoline derivative and herbicide containing the same as active ingredient
CN1376032A (en) Herbicidal composition
CN1042334C (en) Herbicide composition containing 4-benzoyl isoxazole derivative and its use
US5824802A (en) 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides
CN1371244A (en) herbicidal composition
CN1295570A (en) N-pyriconyl herbicides
CN1527812A (en) Novel substituted aniline derivatives having herbicidal activity
CN1310714A (en) Substituted Benzoylcyclohexanediones
DK3160945T3 (en) HERBICID-EFFECTIVE ARYLCARBOXYLIC ACIDAMIDS
CN1376031A (en) Herbicidal composition
CN1468055A (en) Phenylpropynylhydroxypyridine herbicide
CN1045439C (en) Heteroaroyl isoxazole derivatives, their preparation and application, and compositions containing the derivatives
CN1261884A (en) Benzothiophene derivatives used as herbicides
US20020156285A1 (en) Novel herbicides
TW200301078A (en) N-heteroaryl nicotinamid derivatives
CN1332738A (en) 3- (heterocyclyl) -substituted benzoylpyrazoles
JPH03153685A (en) Nitrogen containing n-aryl heterocyclic compound
TW474916B (en) Substituted pyrazol-3-ylbenzazoles
HU202055B (en) Herbicidal composition comprising cyclohexane derivatives and process for producing the active ingredient
JPH04500075A (en) Bactericidal benzodioxanamine derivatives
HK1039335A1 (en) Substituted benzoylcyclohexandiones

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication