WO2023217275A1 - 杂环取代的芳香类化合物及其制备方法、除草组合物和应用 - Google Patents
杂环取代的芳香类化合物及其制备方法、除草组合物和应用 Download PDFInfo
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- WO2023217275A1 WO2023217275A1 PCT/CN2023/093933 CN2023093933W WO2023217275A1 WO 2023217275 A1 WO2023217275 A1 WO 2023217275A1 CN 2023093933 W CN2023093933 W CN 2023093933W WO 2023217275 A1 WO2023217275 A1 WO 2023217275A1
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- Prior art keywords
- alkyl
- cycloalkyl
- substituted
- alkenyl
- halogen
- Prior art date
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- 230000009261 transgenic effect Effects 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
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- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000005516 engineering process Methods 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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- 125000005843 halogen group Chemical group 0.000 claims 3
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M21/00—Apparatus for the destruction of unwanted vegetation, e.g. weeds
- A01M21/04—Apparatus for destruction by steam, chemicals, burning, or electricity
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M21/00—Apparatus for the destruction of unwanted vegetation, e.g. weeds
- A01M21/04—Apparatus for destruction by steam, chemicals, burning, or electricity
- A01M21/043—Apparatus for destruction by steam, chemicals, burning, or electricity by chemicals
-
- 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
-
- 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
- A01N43/82—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 three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
- A01P13/02—Herbicides; Algicides selective
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
-
- 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
-
- 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
-
- 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
- C07D413/10—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 aromatic rings
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Definitions
- the invention belongs to the technical field of pesticides, and specifically relates to a heterocyclically substituted aromatic compound and its preparation method, herbicidal composition and application.
- patent WO2012059050A discloses the use of substituted biarylbenzenesulfonamide compounds as herbicides.
- the herbicidal properties of these known compounds against harmful plants and their selectivity towards crops are not entirely satisfactory.
- the resistance of weeds, the service life of drugs, the economics of drugs and other issues, as well as people's increasing attention to the environment scientists need to continue to research and develop new efficient, safe, economical and different Herbicide varieties with mode of action.
- the invention provides a heterocyclic-substituted aromatic compound and its preparation method, herbicidal composition and application.
- the compound has excellent herbicidal activity against grass weeds, broadleaf weeds, etc. even at low application rates. , with high selectivity for crops.
- a heterocyclic substituted aromatic compound as shown in the general formula I:
- Y represents halogen, haloalkyl, cyano, nitro or amino
- Z represents hydrogen, halogen or hydroxyl
- M 1 and M 2 independently represent CR 5 or N(O) m ;
- R 1 , R 2 , R 3 , R 4 , and R 5 independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, and cycloalkyl. group, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -OR 11 , -SR 11 , -(SO)R 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , - O(SO 2 )R 11 , -N(R 12 ) 2 , phenyl or benzyl, wherein,
- alkyl alkenyl, alkynyl, “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl” or “cycloalkenylalkyl” are each independently unsubstituted or substituted by halogen, the "phenyl” or “benzyl” are independently unsubstituted or selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio Substituted with at least one group among alkyl, alkylsulfonyl, alkoxy or haloalkoxy;
- alkyl are each independently unsubstituted or selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR", -(CO)R", - SR”, -(SO 2 )R”, -O(CO)H, -O(CO)R”, -O-(SO 2 )R”, -(CO)OR”, -O(CO)OR” , -O(CO)(CO)OH, -O(CO)(CO)OR”, at least one group in -O-alkyl-(CO)OH or -O-alkyl-(CO)OR” replaced,
- cycloalkyl are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, halo Alkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO 2 )R 14 , -N(R 14 ) 2 or - O-Alkyl-(CO)OR 14 is substituted by at least one group, or the two adjacent carbon atoms on the ring are unsubstituted or substituted by hal
- amino aminoalkyl
- aminocarbonylalkyl aminocarbonylalkyl
- aminocarbonyloxyalkyl aminocarbonyloxyalkyl
- aminothiocarbonyloxyalkyl aminosulfonyl
- aminonosulfonyl or “aminosulfonyloxy
- Alkyl are each independently unsubstituted or selected from -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -alkyl-(CO)OR 11 , -(SO 2 )
- R' independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aromatic base, arylalkyl, heterocyclyl or heterocyclylalkyl, wherein the "alkyl”, “alkenyl” or “alkynyl” are independently unsubstituted or substituted by halogen, and the "Cycloalkyl", "cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl", “aryl”, “arylalkyl”, “heterocyclyl” or “heterocyclyl”"Alkyl” is each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalky
- R independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocycle base, heterocyclylalkyl or heterocyclylalkenyl, wherein the "alkyl", “alkenyl” or “alkynyl” are independently unsubstituted or selected from halogen, cyano, trialkyl Substituted with at least one group of silyl, -OR 13 , -SR 13 , -O(CO)R 13 , -(CO)R 13 , -(CO)OR 13 or -O(CO)OR 13 , the "cycloalkyl", “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl", "aryl", “arylalkyl”, “arylal
- W 1 represents O, S or NW 4 ;
- W 2 represents OW 3 , SW 3 or NW 4 W 5 ;
- W 3 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, wherein, the "alkyl”, “alkenyl” or “alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl base, heterocyclyl, aryl, substituted by at least one group in, the "cycloalkyl”, “cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, Cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl
- W 4 and W 5 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, wherein, the "alkyl”, “alkenyl” or “alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl base, heterocyclyl, aryl, substituted by at least one group in, the "cycloalkyl”, “cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, Cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by
- NW 4 W 5 stands for Or an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position
- X 11 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or Arylalkyl, wherein the "cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl” , "aryl” or “arylalkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, Haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 14 ,
- X 12 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or aryl Alkyl, wherein the "cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “"Aryl” or “arylalkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, halo Alkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 14 ,
- R 11 each independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cycloalkenyl alkyl group, a phenyl group or a benzyl group, wherein the "alkyl”, “Alkenyl” or “alkynyl” is independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” is independently unsubstituted or selected from halogen, cyano, nitro Substituted with at least one group of alkyl, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;
- R 12 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or -(CO
- the group N(R 12 ) 2 in )N(R 12 ) 2 or -(SO 2 ) N(R 12 ) 2 independently represents an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position;
- R 13 each independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group, or a phenyl group substituted by at least one group selected from the following: halogen, cyano, nitro, alkyl, haloalkyl, Alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or at least one selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy The phenoxy group substituted by the group;
- R 14 each independently represents hydrogen, alkyl, haloalkyl, phenyl or is selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy A phenyl group substituted by at least one group of a group or a haloalkoxy group;
- n 0 or 1.
- Y represents halogen, halogenated C1-C8 alkyl, cyano, nitro or amino.
- Y represents halogen, halogenated C1-C6 alkyl, cyano, nitro or amino.
- R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C8 alkyl, nitro, cyano, C1 -C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1 -C8 alkyl, -OR 11 , -SR 11 , -(SO)R 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -O(SO 2 )R 11 , -N(R 12 ) 2 , phenyl or benzyl, where,
- C1-C8 alkyl C2-C8 alkenyl
- C2-C8 alkynyl C3-C8 cycloalkyl
- C3-C8 cycloalkyl C1-C8 alkyl C3-C8 cycloalkenyl
- C3-C8 cycloalkenyl or “C3-C8 cycloalkenyl C1-C8 alkyl” are independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” are independently unsubstituted.
- R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -OR 11 , -SR 11 , -(SO)R 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -O(SO 2 )R 11 , -N(R 12 ) 2 , phenyl or benzyl, wherein,
- C1-C6 alkyl C2-C6 alkenyl
- C2-C6 alkynyl C3-C6 cycloalkyl
- C3-C6 cycloalkyl C1-C6 alkyl C3-C6 cycloalkenyl
- C3-C6 cycloalkenyl or “C3-C6 cycloalkenyl C1-C6 alkyl” are independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” are independently unsubstituted.
- R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, -OR 11 , -SR 11 , -(SO)R 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -O(SO 2 )R 11 , -N(R 12 ) 2 , phenyl or benzyl, wherein,
- C1-C6 alkyl C2-C6 alkenyl
- C2-C6 alkynyl C3-C6 cycloalkyl
- C3-C6 cycloalkyl C1-C3 alkyl C3-C6 cycloalkenyl
- C3-C6 cycloalkenyl or “C3-C6 cycloalkenyl C1-C3 alkyl” are independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” are independently unsubstituted.
- X 1 , X 2 , X 3 , and Acyl azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -PO(OR') 2 , -OR”, -(CO)R”, -SR”, -(SO)R”, -(SO 2 )R”, -Si(R”) 3 , -O(CO)R”, -O-(SO 2 )R”, -S(CO)R”, -(SO 2 )OR”, -O(CO)OR”, -(CO)OR”, -(CO)OR”, -(CO)OR”, -(CO)OR”, -(CO)OR”, -(CO)OR
- C1-C8 alkyl C2-C8 alkenyl or “C2-C8 alkynyl” are each independently unsubstituted or selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR” , -(CO)R”, -SR”, -(SO 2 )R”, -O(CO)H, -O(CO)R”, -O-(SO 2 )R”, -(CO)OR ”, -O(CO)OR”, -O(CO)(CO)OH, -O(CO)(CO)OR”, -O-(C1-C8 alkyl)-(CO)OH or -O- (C1-C8 alkyl)-(CO)OR" substituted by at least one group,
- C3-C8 cycloalkyl "C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “hetero Cyclyl”, “heterocyclyl C1-C8 alkyl", “aryl” or “aryl C1-C8 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro , C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, Halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8
- amino amino C1-C8 alkyl
- aminocarbonyl C1-C8 alkyl aminocarbonyloxy C1-C8 alkyl
- aminothiocarbonyloxy C1-C8 alkyl aminothiocarbonyloxy C1-C8 alkyl
- sulfamoyl or “sulfamoyloxy C1-C8 alkyl” are each independently unsubstituted or selected from -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -(C1-C8 alkyl)-(CO)OR 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -(C1-C8 alkyl)-(SO 2 )R 11 ,- Substituted by one or two groups in (CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 ;
- R' independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy, C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 Cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl or Heterocyclyl C1-C8 alkyl, wherein the "C1-C8 alkyl", “C2-C8 alkenyl” or "C2-C8 alkynyl” are independently unsubstituted or substituted by halogen, so Said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl",
- R independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl, heterocyclyl C1-C8 alkyl or heterocyclyl C2-C8 Alkenyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl” are independently unsubstituted or selected from halogen, cyano, tri-C1-C8 Alkylsilyl, -OR 13 , -SR 13 , -O(CO)R 13 , -(CO)R 13
- X 1 , X 2 , X 3 , and X 4 independently represent hydrogen, halogen, nitro, cyano, and cyano.
- C1-C6 alkyl C2-C6 alkenyl or “C2-C6 alkynyl” are each independently unsubstituted or selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR” , -(CO)R”, -SR”, -(SO 2 )R”, -O(CO)H, -O(CO)R”, -O-(SO 2 )R”, -(CO)OR ”, -O(CO)OR”, -O(CO)(CO)OH, -O(CO)(CO)OR”, -O-(C1-C6 alkyl)-(CO)OH or -O- (C1-C6 alkyl)-(CO)OR" substituted by 1, 2 or 3 groups,
- C3-C6 cycloalkyl "C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “hetero Cyclyl”, “heterocyclyl C1-C6 alkyl", “aryl” or “aryl C1-C6 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, Halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6
- amino amino C1-C6 alkyl
- aminocarbonyl C1-C6 alkyl aminocarbonyloxy C1-C6 alkyl
- aminothiocarbonyloxy C1-C6 alkyl aminothiocarbonyloxy C1-C6 alkyl
- sulfamoyl or “sulfamoyloxy C1-C6 alkyl” are each independently unsubstituted or selected from -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -(C1-C6 alkyl)-(CO)OR 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -(C1-C6 alkyl)-(SO 2 )R 11 ,- Substituted by one or two groups in (CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 ;
- R' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 Cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or Heterocyclyl C1-C6 alkyl, wherein the "C1-C6 alkyl", “C2-C6 alkenyl” or "C2-C6 alkynyl” are independently unsubstituted or substituted by halogen, so Said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl",
- R independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl, heterocyclyl C1-C6 alkyl or heterocyclyl C2-C6 alkenyl, wherein, the "C1-C6 alkyl", "C2-C6 alkenyl” or " C2-C6 alkynyl” are each independently unsubstituted or selected from halogen, cyano, tri-C1-C6 alkylsilyl, -OR 13 , -SR 13 , -O(CO)R 13 , -( Substi
- C1-C6 alkyl C2-C6 alkenyl or “C2-C6 alkynyl” are each independently unsubstituted or selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR” , -(CO)R”, -SR”, -(SO 2 )R”, -O(CO)H, -O(CO)R”, -O-(SO 2 )R”, -(CO)OR ”, -O(CO)OR”, -O(CO)(CO)OH, -O(CO)(CO)OR”, -O-(C1-C3 alkyl)-(CO)OH or -O- (C1-C3 alkyl)-(CO)OR" substituted by 1, 2 or 3 groups,
- C3-C6 cycloalkyl "C3-C6 cycloalkyl C1-C3 alkyl”, "C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, "hetero Cyclyl”, “heterocyclyl C1-C3 alkyl", “aryl” or “aryl C1-C3 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, Halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C
- amino amino C1-C3 alkyl
- aminocarbonyl C1-C3 alkyl aminocarbonyloxy C1-C3 alkyl
- aminothiocarbonyloxy C1-C3 alkyl aminosulfonyl or “aminosulfonyloxy C1-C3 alkyl”
- aminonosulfonyl or “aminosulfonyloxy C1-C3 alkyl” are each independently unsubstituted or selected from -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -(C1-C3 alkyl)-(CO)OR 11 , -(SO 2 )R 11 , -(SO 2 )OR 11 , -(C1-C3 alkyl)-(SO 2 )R 11 ,- Substituted by one or two groups in (CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 ;
- R' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy, C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, Aryl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, wherein the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 alkynyl” ” are independently unsubstituted or substituted by halogen, and the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “
- R independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl, heterocyclyl C1-C3 alkyl or heterocyclyl C2-C3 Alkenyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, tri-C1-C6 Alkylsilyl, -OR 13 , -SR 13 , -O(CO)R 13 , -(CO)R 13
- W 3 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl ,Aryl, wherein, the "C1-C8 alkyl", “C2-C8 alkenyl” or “C2-C8 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C8 ring Alkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, substituted by at least one group in, the "C3-C8 cycloalkyl", “C3-C8 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected From oxo, halogen, cyano, nitro
- W 4 and W 5 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic group, aryl, wherein, the "C1-C8 alkyl", “C2-C8 alkenyl” or “C2-C8 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C8 ring Alkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, substituted by at least one group in, the "C3-C8 cycloalkyl", “C3-C8 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected From oxo, halogen, cyano, nitro, C
- NW 4 W 5 stands for or It is unsubstituted or substituted with at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;
- X 11 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, C3-C8 cycloalkene base, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein the "C3-C8 cycloalkyl" , "C3-C8 cycloalkyl C1-C8 alkyl", “C3-C8 cycloalkenyl”, "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", “heterocyclyl C1- C8 alkyl", “aryl” or “aryl C1-C8 alkyl” are each
- X 12 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, wherein, the "C3-C8 cycloalkyl", " C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, "C3-C8 cycloalkenyl C1-C8 alkyl", “heterocyclyl", “heterocyclyl C1-C8 alkyl”"yl","aryl” or “aryl C1-C8 alkyl” are
- W 3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocycle base, aryl group
- the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 ring Alkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, substituted by 1, 2 or 3 groups in
- the "C3-C6 cycloalkyl", “C3-C6 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, cyano,
- W 4 and W 5 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic group, aryl,
- the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 ring Alkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, substituted by 1, 2 or 3 groups in
- the "C3-C6 cycloalkyl", “C3-C6 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, cyano, nitro,
- NW 4 W 5 stands for or It is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;
- X 11 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 cycloalkenyl base, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein the "C3-C6 cycloalkyl" , "C3-C6 cycloalkyl C1-C6 alkyl", “C3-C6 cycloalkenyl”, "C3-C6 cycloalkenyl C1-C6 alkyl", “heterocyclyl", “heterocyclyl C1- C6 alkyl", “aryl” or “aryl C1-C6 alkyl”
- X 12 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein, the "C3-C6 cycloalkyl", " C3-C6 cycloalkyl C1-C6 alkyl", “C3-C6 cycloalkenyl”, "C3-C6 cycloalkenyl C1-C6 alkyl", “heterocyclyl", “heterocyclyl C1-C6 alkyl”"yl","aryl” or "aryl C1-C6 alkyl” are
- W 3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocycle base, aryl group
- the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 ring Alkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, substituted by 1, 2 or 3 groups in
- the "C3-C6 cycloalkyl", “C3-C6 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, cyano,
- W 4 and W 5 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic group, aryl,
- the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 ring Alkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, substituted by 1, 2 or 3 groups in
- the "C3-C6 cycloalkyl", “C3-C6 cycloalkenyl", “heterocyclyl” or “aryl” are independently unsubstituted or selected from oxo, halogen, cyano, nitro,
- NW 4 W 5 stands for or It is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;
- X 11 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C3 alkyl, C3-C6 cycloalkene base, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein the "C3-C6 cycloalkyl" , "C3-C6 cycloalkyl C1-C3 alkyl", “C3-C6 cycloalkenyl”, "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", “heterocyclyl C1- C3 alkyl", “aryl” or “aryl C1-C3 alkyl” are each
- X 12 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein, the "C3-C6 cycloalkyl", " C3-C6 cycloalkyl C1-C3 alkyl", “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl", “heterocyclyl", “heterocyclyl C1-C3 alkyl”"yl","aryl” or "aryl C1-C3 alkyl” are
- R 11 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or benzyl, wherein the "C1-C8 alkyl", “C2-C8 alkenyl” or “C2-C8 alkyne "Group” is independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” is independently unsubstituted or selected from halogen, cyano, nitro, C1-C8 alkyl , at least one of halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C
- R 12 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3- C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or -(CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 in the group N(R 12 ) 2 independently represent It is unsubstituted or substituted with at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;
- R 13 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl or Phenyl group substituted by at least one of the following groups: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy , C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl or selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1 Phenoxy group substituted by at least one group of -C8 alkoxy or halogenated C1-C8 alkoxy;
- R 14 independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, A phenyl group substituted by at least one of C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.
- R 11 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl , C3-C6 cycloalkenyl, C3-C6 cycloalkenyl, C1-C6 alkyl, phenyl or benzyl, wherein the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 "Alkynyl” is independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” is independently unsubstituted or selected from halogen, cyano, nitro, C1-C6 alkyl group, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6
- R 12 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3- C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or -(CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 in the group N(R 12 ) 2 independently represent It is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;
- R 13 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or benzene substituted by 1, 2 or 3 groups selected from the following Base: Halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1- C6 alkylthio, C1-C6 alkylsulfonyl or selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 Phenoxy group substituted by 1, 2 or 3 groups in the alkoxy group;
- R 14 independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, Substituted with 1, 2 or 3 groups of C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy of phenyl.
- R 11 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl , C3-C6 cycloalkenyl, C3-C6 cycloalkenyl, C1-C3 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", “C2-C6 alkenyl” or “C2-C6 "Alkynyl” is independently unsubstituted or substituted by halogen, and the "phenyl” or “benzyl” is independently unsubstituted or selected from halogen, cyano, nitro, C1-C6 alkyl group, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6
- R 12 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3- C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C3 alkyl, or the group N(R 12 ) 2 in -(CO)N(R 12 ) 2 or -(SO 2 )N(R 12 ) 2 independently represents It is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;
- R 13 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or benzene substituted by 1, 2 or 3 groups selected from the following Base: Halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1- C6 alkylthio, C1-C6 alkylsulfonyl or selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 Phenoxy group substituted by 1, 2 or 3 groups in the alkoxy group;
- R 14 independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, Substituted with 1, 2 or 3 groups of C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy of phenyl.
- Alkyl groups with more than two carbon atoms can be straight chain or branched chain.
- the alkyl group in the compound word "-alkyl-(CO)OR 11 " can be -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )-, -C(CH 3 ) 2 -, etc.
- Alkyl groups are, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl base, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl.
- alkenyl is for example vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl base, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl.
- Alkynyl groups are, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position on each unsaturated group.
- Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be in any position.
- Halogen is fluorine, chlorine, bromine or iodine.
- aryl as used herein includes, but is not limited to, phenyl, naphthyl
- the "heterocyclic group” includes but is not limited to saturated or unsaturated non-aromatic cyclic groups. etc., also includes but is not limited to heteroaryl, that is, an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally having a benzo ring fused, 1 to 4 of the ring atoms ( For example 1, 2, 3 or 4) heteroatoms selected from oxygen, nitrogen and sulfur, e.g.
- a group is substituted by a group, this is understood to mean that the group is substituted by one or more groups, which may be identical or different, selected from those mentioned.
- the same or different substitution characters contained in the same or different substituents are independently selected and may be the same or different. The same applies to ring systems formed from different atoms and units. At the same time, the scope of the claims is to exclude compounds which are known to those skilled in the art to be chemically unstable under standard conditions.
- substituted by at least one group refers to being substituted by, for example, 1, 2, 3, 4 or 5 groups; groups whose specific connection positions are not indicated (including heterogeneous groups) Cyclic group, aryl group, etc.), can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it complies with the bond connection rules.
- heteroaryl substituted by 1 methyl group representative wait Such as heteroaryl substituted by 1 methyl group representative wait.
- the stereochemical configuration at the position marked * in formula I is determined as the main (R) or (S) according to the Cahn-Ingold-Prelog system.
- the subject of the present invention also relates to those included in formula I. All stereoisomers at other positions, and mixtures thereof.
- Such compounds of formula I contain, for example, one or more additional asymmetric carbon atoms or other compounds not specified in formula I. Illustrated double bond.
- the present invention includes the pure isomers and mixtures thereof enriched to varying degrees of the pure isomers, wherein the asymmetric carbon atom at the position marked * is in the R-configuration or the S-configuration, or in a mixture in which a compound or compounds of the same chemical structure have the R-configuration or the S-configuration at the position marked *, or compounds having the R-configuration or the S-configuration are predominantly present (at least 60% R-configuration or S-configuration), while other asymmetric carbon atoms may exist in racemic form, or may undergo resolution to varying degrees.
- stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-, provided that the conditions for the stereochemical configuration at the position marked * are met
- the isomers are all included in formula I and may be obtained from mixtures of stereoisomers by conventional methods or may be prepared by stereoselective reactions in combination with stereochemically pure starting materials.
- the present invention also includes any ketone and enol tautomeric forms and mixtures and salts thereof.
- Stereoisomers can be obtained by optical resolution from the mixture obtained in the preparation. Stereoisomers can also be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries.
- conventional methods can generally be used (see Textbooks of Stereochemistry), such as those described below for the resolution of mixtures into diastereoisomers, e.g. physical methods such as crystallization, chromatography, in particular It is column chromatography and high-pressure liquid chromatography, distillation methods carried out under reduced pressure if necessary, extraction methods and other methods, usually using chromatographic separation on a chiral solid phase, to separate the residual mixture of enantiomers.
- Suitable for preparative quantities or for use on an industrial scale are methods such as crystallization of diastereomeric salts, which can be obtained from the compounds using optically active acids and, if acidic groups are present, optionally optically active bases.
- the preparation method of the heterocyclic substituted aromatic compound includes the following steps:
- Hal represents halogen, preferably Cl; the substituents X 1 , X 2 , R 1 , R 2 , R 3 , R 4 , M 1 , M 2 , Q, Y and Z are as defined above;
- the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from nitrogen-containing bases (such as C1-C6 alkylamines, preferably tris-(C1-C6)-alkylamines, e.g. At least one of triethylamine, trimethylamine, N-ethyldiisopropylamine);
- nitrogen-containing bases such as C1-C6 alkylamines, preferably tris-(C1-C6)-alkylamines, e.g. At least one of triethylamine, trimethylamine, N-ethyldiisopropylamine
- the solvent is selected from aromatic hydrocarbons (such as benzene, chlorobenzene, toluene, cresol or o-, m- and p-xylene), THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, At least one of Dioxane, methylene chloride, toluene or ethyl acetate.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresol or o-, m- and p-xylene
- the compound represented by general formula II can be prepared by referring to the methods shown in WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 or WO19145245.
- a herbicide composition which includes a herbicidal effective amount of at least one of the heterocyclic substituted aromatic compounds, and preferably also includes a formulation auxiliary.
- a method for controlling weeds which comprises adding a herbicidally effective amount of at least one of the heterocyclic substituted aromatic compounds
- One or more herbicidal compositions are applied to plants or weedy areas.
- heterocyclically substituted aromatic compounds or the herbicide composition in controlling weeds.
- the heterocyclically substituted aromatic compounds are used for controlling useful crops. weeds, and the useful crops are transgenic crops or crops treated with genome editing technology.
- the compounds of formula I according to the invention have outstanding herbicidal activity against many economically important monocotyledonous and dicotyledonous harmful plants.
- the active substances according to the invention are also effective against perennial weeds which grow from rhizomes, rhizomes or other perennial organs and are difficult to control. In this regard, it generally does not matter whether the substance is applied before sowing, before germination or after germination. Special mention is made of representative examples of monocotyledonous and dicotyledonous weed groups which can be controlled by the compounds of the invention, without being limited to specific species.
- weed species on which the active substances act effectively include monocotyledonous plants: annual Oats, rye, grasses, caladium, phalanx, barnyardgrass, crabgrass, setaria and sedge, and perennial icegrass Grasses, Bermudagrass, Imperata and Sorghum, as well as perennial sedges.
- dicotyledonous weed species its role can be extended to species such as annuals of the spp. spp., Matricaria and Amaranthus, and the perennial weeds Convolvulus, Thistle, Sorrel and Wormwood.
- the active substance of the present invention effectively controls harmful plants, such as Echinacea, Sagittaria, Alisma, Water Chestnut, Saccharomyces and Cyperus under the undetermined conditions of rice sowing. If the compounds according to the invention are applied to the soil surface before emergence, the seedlings of weeds can be completely prevented before they appear, or the growth of the weeds can be stopped as soon as they develop cotyledons and finally die completely after three to four weeks.
- the compounds of the present invention have particularly excellent activity against the following plants: apilla, sesame, Polygonum curly, chickweed, ivy leaf, Arabidopsis, pansy and amaranth, Bosphorus and Kochia .
- the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they do not damage important commercial crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans at all. , or the damage is insignificant. It is particularly compatible with cereal crops such as wheat, barley and corn, especially wheat. The compounds of the invention are therefore very suitable for the selective control of unwanted plants in agricultural crops or ornamental plants.
- these active substances can be used to control harmful plants in known or upcoming genetically engineered plant cultivations.
- Genetically modified plants often have superior traits, such as resistance to specific pesticides, especially specific herbicides, resistance to plant diseases or plant disease-causing microorganisms, such as specific insects or fungal, bacterial or viral microorganisms.
- Other special properties are related to the following conditions of the product, such as quantity, quality, storage stability, composition and special ingredients.
- the transgenic plant products obtained have increased starch content or improved starch quality or different fatty acid composition.
- the compounds of formula I or their salts according to the invention are preferably used in economically important transgenic crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in sugar beet, Cultivation of cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants.
- the compounds of the formula I are preferably used as herbicides in the cultivation of useful plants which are resistant to the herbicides or which have been genetically engineered to be resistant to the toxic effects of the herbicides.
- nucleic acid molecules may be introduced into plasmids, and mutations or sequence changes may occur through the recombination of DNA sequences. Using the standard methods described above, it is possible, for example, to exchange substrates, remove partial sequences or add natural or synthetic sequences. In order to connect DNA fragments to each other, it is possible to attach conjugates or linkers to the fragments.
- Plant cells with reduced activity gene products can be prepared by the following methods, for example, by expressing at least one appropriate antisense-RNA, sense-RNA to achieve a co-suppressive effect, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcripts of the above gene products.
- DNA molecules that contain the entire coding sequence of the gene product including any flanking sequences that may be present, and to use DNA molecules that contain only part of the coding sequence, which parts must be long enough to achieve antisense expression in the cell. Effect. Sequences that are highly homologous to, but not identical to, the gene product coding sequence may also be used.
- the synthesized proteins can be localized in any desired plant cell compartment.
- These sequences are known to those skilled in the art (see, e.g., Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).
- Transgenic plant cells can be reconstituted into whole plants using known techniques.
- the active substance of the present invention When the active substance of the present invention is used on transgenic crops, in addition to the effect of suppressing harmful plants that can be observed on other crops, there will often be special effects on the corresponding transgenic crops, such as improved or expanded control. range of weeds, improved application rates, preferably a good combination of resistance and herbicide performance in the transgenic crop, and the impact on plant growth and yield of the transgenic crop.
- the present invention therefore also provides the use of said compounds as herbicides for controlling harmful plants in transgenic crop plants.
- the compounds of the present invention can significantly regulate the growth of crop plants. By participating in the regulation of plant metabolism, these compounds are used to target plant components and enhance harvesting, such as drying out and stunting growth. And they are also suitable for regulating and suppressing undesirable plant growth without damaging crop growth. Inhibiting plant growth plays a very important role in many monocot and dicot crops, as lodging can be reduced or completely prevented.
- the compounds of the invention can be applied using the usual formulations, wettable powders, concentrated emulsions, sprayable solutions, powders or granules.
- the present invention also provides herbicidal compositions comprising compounds of formula I.
- the compounds of formula I can be formulated in a variety of ways, depending on the usual biological and/or chemical physical parameters.
- Suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsions concentrates (EC), for example oil-in-water and water-in-oil emulsions (EW) , sprayable solution, suspension concentrate (SC), dispersible oil suspension (OD), suspension with oil or water as diluent, miscible oil solution, powder (DP), capsule suspension (CS) ), seeddressing compositions, granules for broadcasting and soil application, spray granules, coated granules and absorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra low volume) formulations, microcapsules and wax products.
- WP wettable powders
- SP water-soluble powders
- EC emulsions concentrates
- EW oil-in-water and water-in-oil emulsions
- SC dispersible oil suspension
- DP
- the necessary formulation auxiliaries such as inert substances, surfactants, solvents and other additives are also known and are described in, for example, Watkins'"Handbook of Powdered Diluent Pesticides and Carriers", 2nd edition, Darland Book Caldwell NJ; Hv01phen "An Introduction to Clay Colloidal Chemistry", 2nd ed., J. Wiley and Sons, NY; C.
- Wettable powders can be uniformly dispersed in water.
- active substances they also include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, poly Ethoxylated fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkylphenyl sulfonate, sodium lignosulfonate, 2,2'-dinaphthylmethane -Sodium 6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoylmethyltaurate.
- the herbicide active substances are finely ground, for example using customary instruments, such as hammer mills, fan mills and jet mills, and auxiliaries are mixed simultaneously or sequentially.
- Concentrated emulsions are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or higher boiling aromatics or hydrocarbons or mixtures of solvents, and adding a One or more ionic and/or nonionic surfactants (emulsifiers).
- organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or higher boiling aromatics or hydrocarbons or mixtures of solvents.
- emulsifiers examples include calcium alkyl aryl sulfonates, such as calcium dodecyl benzene sulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ethers, oxypropylene-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitol such as polyoxyethylene sorbitan fatty acid esters Polysaccharide esters.
- calcium alkyl aryl sulfonates such as calcium dodecyl benzene sulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ethers, oxypropylene-ethylene oxide condensation products, alkyl polyethers,
- a powder is obtained by grinding the active substance and finely divided solid substances such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- Suspensions based on water or oil can be prepared by, for example, wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of another formulation type mentioned above.
- Emulsions such as oil-in-water emulsions (EW) can be prepared using an aqueous organic solvent, using a stirrer, a colloid mill and/or a static mixer and, if necessary, adding a surfactant of another formulation type as described above.
- EW oil-in-water emulsions
- granules by the following method: spray the active material onto the adsorbent and use inert materials to granulate it, or concentrate the active material onto the surface of a carrier such as sand or kaolinite, granulate the inert material through a binder, and stick it to Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil.
- Suitable active substances can be granulated in the same manner as fertilizer granules and, if desired, mixed with fertilizer. Water-suspended granules are prepared using common methods, such as spray-drying, fluidized bed granulation, grinding disc granulation, mixing using a high-speed mixer, and extrusion without solid inert materials.
- Agrochemical preparations generally contain from 0.1 to 99%, in particular from 0.1 to 95% by weight of the active substance of the formula I.
- the concentration of active substance in wettable powders is, for example, from approximately 10 to 99% by weight, with the usual composition of the formulation components remaining to 100% by weight.
- the concentration of active substance in the emulsion concentrate may be from about 1 to 90%, preferably from 5 to 80% by weight.
- Powder formulations contain from 1 to 30% by weight of active substance, usually preferably from 5 to 20% by weight of active substance, whereas sprayable solutions contain from approximately 0.05 to 80% by weight, preferably from 2 to 50% by weight of active substance. .
- the content of active substances in water-suspended granules mainly depends on whether the active substances are liquid or solid, and the additives, fillers, etc. used during granulation.
- the content of active substance in the aqueous suspension granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- the formulation of the active substance may include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, defoaming agents, evaporation inhibitors and Commonly used pH and viscosity regulators in all situations.
- suitable active substances that can be mixed with the active substances of the present invention are, for example, "Encyclopedia of New Pesticide Varieties in the World", China Agricultural Science and Technology Press, 2010.9 and in the literature cited here Known substances.
- the herbicidal active substances mentioned below can be mixed with mixtures of formula I, (Note: the name of the compound is either its common name according to the International Organization for Standardization (ISO) or its chemical name, with a code name when appropriate): Acetate Amine, butachlor, alachlor, metolachlor, metolachlor, sperm metolachlor, metolachlor, picochlor, gramchlor, naprofenamide, R-levonaprofen Amoxamide, propanil, fenacetamide, diphenylpyrmid, flufenacet, flufenacet, flubutyfen, brombutyfen, dimethiofen, high-efficiency dimethyl Cifenacet, ethoxyfenacet, flufenacet, methoxyfenacet, metazachlor, clomazone, high-efficiency wheatgrass methyl ester, high-efficiency wheatgrass propylpropyl, diphenylchlor, methoxy
- the required dosage of the compound of formula I varies with changes in external conditions, such as temperature, humidity, the nature of the herbicide used, etc. It can vary widely, for example between 0.001 and 1.0kg a.i./ha, or more active substance, but is preferably between 0.005 and 750g
- a.i./ha especially between 0.005 and 250g a.i./ha.
- the activity level criteria for plant damage i.e. growth control rate are as follows:
- Level 9 Growth control rate is greater than or equal to 90% and less than 100%
- Level 8 Growth control rate is greater than or equal to 80% and less than 90%
- Level 7 Growth control rate is greater than or equal to 70% and less than 80%;
- Growth control rate is greater than or equal to 60% and less than 70%
- Level 5 Growth control rate is greater than or equal to 50% and less than 60%;
- Level 4 Growth control rate is greater than or equal to 40% and less than 50%;
- Level 3 Growth control rate is greater than or equal to 30% and less than 40%;
- Level 2 Growth control rate is greater than or equal to 20% and less than 30%;
- the above growth control rate is the fresh weight control rate.
- Seeds of monocotyledonous and dicotyledonous weeds (artemisia, shepherd's purse, amaranth, pigweed, chickweed, amaranth, amaranth, amaranth, Japanese amaranth, cowgrass, wormwood, hardweed) Grass, fleabane, candleweed, mother-of-pearl, brome, knotweed, amaranth, amaranth retroflexus, pigweed, commelder, endive, bindweed, amaranth, nightshade, amaranth, horsetail Tang, barnyard grass, green foxtail, golden foxtail, stephanotis, duck tongue, arrowhead, firefly, cyperus, broken rice sedge, special-shaped sedge, flutter grass, purslane, cocklebur, morning glory, white wine Grass, etc.) and main crop seeds (wheat, corn, rice, soybeans, cotton, rapeseed, millet, sorg
- the compound of the present invention to be tested is dissolved in acetone, then Tween 80 is added, diluted with a certain amount of water to a solution of a certain concentration, and sprayed immediately after sowing. After the application, the experimental results were observed after 4 weeks of cultivation in the greenhouse.
Abstract
本发明属于农药技术领域,具体涉及一种杂环取代的芳香类化合物及其制备方法、除草组合物和应用。所述化合物如通式I所示:其中,Y代表卤素、卤代烷基、氰基、硝基或氨基;Z代表氢、卤素或羟基;M1、M2分别独立地代表CR5或N(O)m;Q代表CX3X4;R1、R2、R3、R4、R5分别独立地代表氢、卤素等;X1、X2、X3、X4分别独立地代表氢、卤素等,m代表0或1。所述化合物即使在低施用率下对禾本科杂草、阔叶杂草等也具有优异的除草活性,并对作物具有高选择性。
Description
本发明属于农药技术领域,具体涉及一种杂环取代的芳香类化合物及其制备方法、除草组合物和应用。
杂草的防治是实现高效农业过程中一个至关重要的环节,尽管市场上的除草剂种类多样,比如专利WO2012059050A等公开了取代的联芳香基苯磺酰胺类化合物作为除草剂的用途。然而,这些已知化合物对有害植物的除草性能和对作物的选择性并不完全令人满意。且由于市场的不断扩大、杂草的抗性、药物的使用寿命以及药物的经济性等问题以及人们对环境的日益重视,需要科学家们不断研究进而开发出新的高效、安全、经济以及具有不同作用方式的除草剂品种。
发明内容
本发明提供了一种杂环取代的芳香类化合物及其制备方法、除草组合物和应用,所述化合物即使在低施用率下对禾本科杂草、阔叶杂草等也具有优异的除草活性,并对作物具有高选择性。
本发明采用的技术方案如下:
一种杂环取代的芳香类化合物,如通式I所示:
其中,
Y代表卤素、卤代烷基、氰基、硝基或氨基;
Z代表氢、卤素或羟基;
M1、M2分别独立地代表CR5或N(O)m;
Q代表CX3X4;
R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基烷基、硝基、氰基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,
所述“烷基”、“烯基”、“炔基”、“环烷基”、“环烷基烷基”、“环烯基”或“环烯基烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的;
X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、
-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基烷基、芳基、芳基烷基、氨基、氨基烷基、氨基羰基烷基、氨基羰基氧基烷基、氨基硫代羰基氧基烷基、氨基磺酰基或氨基磺酰基氧基烷基,其中,
所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-烷基-(CO)OH或-O-烷基-(CO)OR”中的至少一个基团所取代的,
所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,
所述“氨基”、“氨基烷基”、“氨基羰基烷基”、“氨基羰基氧基烷基”、“氨基硫代羰基氧基烷基”、“氨基磺酰基”或“氨基磺酰基氧基烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-烷基-(CO)OR11、-(SO2)R11、-(SO2)OR11、-烷基-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;
R’分别独立地代表氢、卤素、烷氧基、烷氧基烷基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、杂环基或杂环基烷基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“杂环基”或“杂环基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
R”分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、芳基烯基、杂环基、杂环基烷基或杂环基烯基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、三烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的至少一个基团所取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“芳基烯基”、“杂环基”、“杂环基烷基”或“杂环基烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
W1代表O、S或NW4;
W2代表OW3、SW3或NW4W5;
W3分别独立地代表氢、烷基、烯基、炔基、环烷基、环烯基、杂环基、芳基、
其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、环烷基、三烷基甲硅烷基、环烯基、杂环基、芳基、
中的至少一个基团所取代的,所述“环烷基”、“环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
W4、W5分别独立地代表氢、烷基、烯基、炔基、环烷基、环烯基、杂环基、芳基、
其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、环烷基、三烷基甲硅烷基、环烯基、杂环基、芳基、
中的至少一个基团所取代的,所述“环烷基”、“环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
或者NW4W5代表或者未取代或取代的1-位为氮原子的杂环基;
X11分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、杂环基、杂环基烷基、芳基或芳基烷基,其中,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X12分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、杂环基、杂环基烷基、芳基或芳基烷基,其中,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X13、X14分别独立地代表氢、卤素、氰基、烷氧基、烷氧基烷基、烷基羰基、烷氧基羰基、烷基磺酰基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、杂环基或杂环基烷基,或者基团CX13X14一起形成未取代或取代的环状结构,或者基团NX13X14一起形成未取代或取代的1-位为氮原子的杂环基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“杂环基”或“杂环基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
R11分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、苯基或苄基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的;
R12分别独立地代表氢、烷基、烯基、炔基、烷氧基、烷基磺酰基、环烷基、环烷基烷基、环烯基或环烯基烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表未取代或取代的1-位为氮原子的杂环基;
R13分别独立地代表烷基、烯基、炔基、环烷基、苯基或被选自以下至少一个基团所取代的苯基:卤素,氰基,硝基,烷基,卤代烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基磺酰基或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基或卤代烷氧基中的至少一个基团所取代的苯氧基;
R14分别独立地代表氢,烷基,卤代烷基,苯基或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的苯基;
m代表0或1。
在一个具体实施方式中,Y代表卤素、卤代C1-C8烷基、氰基、硝基或氨基。
在另一个具体实施方式中,Y代表卤素、卤代C1-C6烷基、氰基、硝基或氨基。
在一个具体实施方式中,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C8烷基、硝基、氰基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、-OR11、-SR11、
-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,
所述“C1-C8烷基”、“C2-C8烯基”、“C2-C8炔基”、“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”或“C3-C8环烯基C1-C8烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的。
在另一个具体实施方式中,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C6烷基、硝基、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,
所述“C1-C6烷基”、“C2-C6烯基”、“C2-C6炔基”、“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”或“C3-C6环烯基C1-C6烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的。
在另一个具体实施方式中,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C6烷基、硝基、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,
所述“C1-C6烷基”、“C2-C6烯基”、“C2-C6炔基”、“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”或“C3-C6环烯基C1-C3烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的。
在一个具体实施方式中,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C8烷基、芳基、芳基C1-C8烷基、氨基、氨基C1-C8烷基、氨基羰基C1-C8烷基、氨基羰基氧基C1-C8烷基、氨基硫代羰基氧基C1-C8烷基、氨基磺酰基或氨基磺酰基氧基C1-C8烷基,其中,
所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C8烷基)-(CO)OH或-O-(C1-C8烷基)-(CO)OR”中的至少一个基团所取代的,
所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,
所述“氨基”、“氨基C1-C8烷基”、“氨基羰基C1-C8烷基”、“氨基羰基氧基C1-C8烷基”、“氨基硫代羰基氧基C1-C8烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C8烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C8烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C8烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;
R’分别独立地代表氢、卤素、C1-C8烷氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、杂环基或杂环基C1-C8烷基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“杂环基”或“杂环基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
R”分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、芳基C2-C8烯基、杂环基、杂环基C1-C8烷基或杂环基C2-C8烯基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C8烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“芳基C2-C8烯基”、“杂环基”、“杂环基C1-C8烷基”或“杂环基C2-C8烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环。
在另一个具体实施方式中,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰
硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C6烷基、芳基、芳基C1-C6烷基、氨基、氨基C1-C6烷基、氨基羰基C1-C6烷基、氨基羰基氧基C1-C6烷基、氨基硫代羰基氧基C1-C6烷基、氨基磺酰基或氨基磺酰基氧基C1-C6烷基,其中,
所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C6烷基)-(CO)OH或-O-(C1-C6烷基)-(CO)OR”中的1、2或3个基团所取代的,
所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,
所述“氨基”、“氨基C1-C6烷基”、“氨基羰基C1-C6烷基”、“氨基羰基氧基C1-C6烷基”、“氨基硫代羰基氧基C1-C6烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C6烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C6烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C6烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;
R’分别独立地代表氢、卤素、C1-C6烷氧基、C1-C6烷氧基C1-C6烷基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、杂环基或杂环基C1-C6烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“杂环基”或“杂环基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
R”分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、芳
基C2-C6烯基、杂环基、杂环基C1-C6烷基或杂环基C2-C6烯基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C6烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“芳基C2-C6烯基”、“杂环基”、“杂环基C1-C6烷基”或“杂环基C2-C6烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环。
在另一个具体实施方式中,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C3烷基、芳基、芳基C1-C3烷基、氨基、氨基C1-C3烷基、氨基羰基C1-C3烷基、氨基羰基氧基C1-C3烷基、氨基硫代羰基氧基C1-C3烷基、氨基磺酰基或氨基磺酰基氧基C1-C3烷基,其中,
所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C3烷基)-(CO)OH或-O-(C1-C3烷基)-(CO)OR”中的1、2或3个基团所取代的,
所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,
所述“氨基”、“氨基C1-C3烷基”、“氨基羰基C1-C3烷基”、“氨基羰基氧基C1-C3烷基”、“氨基硫代羰基氧基C1-C3烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C3烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C3烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C3烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;
R’分别独立地代表氢、卤素、C1-C6烷氧基、C1-C6烷氧基C1-C3烷基、C1-C6烷基、
C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、杂环基或杂环基C1-C3烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“杂环基”或“杂环基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
R”分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、芳基C2-C3烯基、杂环基、杂环基C1-C3烷基或杂环基C2-C3烯基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C6烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“芳基C2-C3烯基”、“杂环基”、“杂环基C1-C3烷基”或“杂环基C2-C3烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环。
在一个具体实施方式中,W3分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、杂环基、芳基、
其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C8环烷基、三C1-C8烷基甲硅烷基、C3-C8环烯基、杂环基、芳基、
中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相
邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
W4、W5分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、杂环基、芳基、
其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C8环烷基、三C1-C8烷基甲硅烷基、C3-C8环烯基、杂环基、芳基、
中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
或者NW4W5代表或者其是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的;
X11分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、杂环基、杂环基C1-C8烷基、芳基或芳基C1-C8烷基,其中,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X12分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、杂环基、杂环基C1-C8烷基、芳基或芳基C1-C8烷基,其中,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、
-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X13、X14分别独立地代表氢、卤素、氰基、C1-C8烷氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷基磺酰基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、杂环基或杂环基C1-C8烷基,或者基团CX13X14一起形成5~8元碳环或含氧、硫或氮的杂环,或者基团NX13X14一起形成
其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“杂环基”或“杂环基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元碳环或含氧、硫或氮的杂环”是未取代的或被选自C1-C8烷基、C1-C8烷氧羰基或苄基中的至少一个基团所取代的,或者与芳基或杂环基形成稠环结构;所述是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的。
在另一个具体实施方式中,W3分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、
其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、
中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
W4、W5分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、
其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、
中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
或者NW4W5代表或者其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;
X11分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、杂环基、杂环基C1-C6烷基、芳基或芳基C1-C6烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X12分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、杂环基、杂环基C1-C6烷基、芳基或芳基C1-C6烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、
-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X13、X14分别独立地代表氢、卤素、氰基、C1-C6烷氧基、C1-C6烷氧基C1-C6烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基磺酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、杂环基或杂环基C1-C6烷基,或者基团CX13X14一起形成5~8元饱和碳环、或者基团NX13X14一起形成其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“杂环基”或“杂环基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元饱和碳环、”是未取代的或被选自C1-C6烷基、C1-C6烷氧羰基或苄基中的1、2或3个基团所取代的,或者与芳基或杂环基形成稠环结构,所述是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的。
在另一个具体实施方式中,W3分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、
其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、
中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
W4、W5分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、
其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、
中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
或者NW4W5代表或者其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;
X11分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、杂环基、杂环基C1-C3烷基、芳基或芳基C1-C3烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X12分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、杂环基、杂环基C1-C3烷基、芳基或芳基C1-C3烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、
-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;
X13、X14分别独立地代表氢、卤素、氰基、C1-C6烷氧基、C1-C6烷氧基C1-C3烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基磺酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、杂环基或杂环基C1-C3烷基,或者基团CX13X14一起形成5~8元饱和碳环、或者基团NX13X14一起形成其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“杂环基”或“杂环基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元饱和碳环、”是未取代的或被选自C1-C6烷基、C1-C6烷氧羰基或苄基中的1、2或3个基团所取代的,或者与苯基或噻吩基形成稠环结构;所述是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的。
在一个具体实施方式中,R11分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、苯基或苄基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的;
R12分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C1-C8烷氧基、C1-C8烷基磺酰基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基或C3-C8环烯基C1-C8烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表
其是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的;
R13分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、苯基或被
选自以下至少一个基团所取代的苯基:卤素,氰基,硝基,C1-C8烷基,卤代C1-C8烷基,C1-C8烷氧基,卤代C1-C8烷氧基,C1-C8烷氧基羰基,C1-C8烷硫基,C1-C8烷基磺酰基或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的苯氧基;
R14分别独立地代表氢,C1-C8烷基,卤代C1-C8烷基,苯基或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的苯基。
在另一个具体实施方式中,R11分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、苯基或苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的;
R12分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷基磺酰基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基或C3-C6环烯基C1-C6烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表
其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;
R13分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、苯基或被选自以下1、2或3个基团所取代的苯基:卤素,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基羰基,C1-C6烷硫基,C1-C6烷基磺酰基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯氧基;
R14分别独立地代表氢,C1-C6烷基,卤代C1-C6烷基,苯基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯基。
在另一个具体实施方式中,R11分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、苯基、苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的;
R12分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷基磺酰基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基或C3-C6环烯基
C1-C3烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表
其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;
R13分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、苯基或被选自以下1、2或3个基团所取代的苯基:卤素,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基羰基,C1-C6烷硫基,C1-C6烷基磺酰基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯氧基;
R14分别独立地代表氢,C1-C6烷基,卤代C1-C6烷基,苯基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯基。
在上述通式所示化合物的定义和以下所有结构式中,所用专业术语不论单独使用或者使用在复合词中,代表如下取代基:具有多于两个碳原子的烷基基团可为直链或支链的。如复合词“-烷基-(CO)OR11”中烷基可为-CH2-、-CH2CH2-、-CH(CH3)-、-C(CH3)2-等。烷基基团为,例如,C1烷基-甲基;C2烷基-乙基;C3烷基-丙基如正丙基或异丙基;C4烷基-丁基如正丁基、异丁基、叔丁基或2-丁基;C5烷基-戊基如正戊基;C6烷基-己基如正己基、异己基和1,3-二甲基丁基。类似地,烯基是例如乙烯基、烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-1-基和1-甲基丁-2-烯-1-基。炔基是例如乙炔基、炔丙基、丁-2-炔-1-基、丁-3-炔-1-基、1-甲基丁-3-炔-1-基。多重键可以在每个不饱和基团的任何位置。环烷基是具有例如三至六个碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基。类似地,环烯基是具有例如三至六个碳环成员的单环烯基,例如环丙烯基、环丁烯基、环戊烯基和环己烯基,其中双键可以在任何位置。卤素为氟、氯、溴或碘。
除非有特别说明的,本发明所述“芳基”包括但不限于苯基、萘基、
所述“杂环基”不仅包括但不限于饱和或不饱和的非芳族环状基团
等,还包括但不限于杂芳基,即含有例如3至6个环原子且还任选地有苯并环稠合的芳族环状基团,所述环原子中的1至4个(例如1、2、
3或4个)杂原子选自氧、氮和硫,例如
如果一个基团被基团所取代,则这应理解为意指该基团被一个或多个相同或不同的选自所提及的那些基团的基团取代。另外,相同或不同取代基中含有的相同或不同的取代字符均独立地选择,可相同也可不同。这同样适用于由不同原子和单元形成的环体系。同时,权利要求的范围将排除那些为本领域技术人员知晓的在标准条件下化学不稳定的化合物。
另外,除非特别限定地,本发明所述“至少一个基团所取代的”是指被如1、2、3、4或5个基团所取代;未标注具体连接位置的基团(包括杂环基、芳基等),可在任意位置连接,包括与C或N相连接的位置;如果其是被取代的,取代基同样可在任何位置取代,只要符合化合键连接规则。如被1个甲基所取代的杂芳基可代表等。
需要指出的,当通式I中与X1和X2相连的碳原子(C*)为手性中心(即X1和X2不相同时)时,其为R构型或S构型。
本发明中,式I中标记为*的位置处的立体化学构型是根据Cahn-Ingold-Prelog系统来确定为主要的(R)或(S),然而本发明的主题也涉及式I所包括的其它位置的所有立体异构体,及其混合物。这类式I化合物包含,例如一种或多种附加的不对称碳原子或其它未在式I中具体
说明的双键。应理解的是,本发明包括纯异构体及其程度不同的富集纯异构体的混合物,其中在标记为*的位置处的不对称碳原子是R-构型或S-构型,或在混合物中,化合物或同样化学构造的化合物在标记为*的位置上具有R-构型或S-构型,或以主要存在具有R-构型或S-构型的化合物(至少60%R-构型或S-构型)的比例存在,同时其它的不对称碳原子可以以外消旋形式存在,或也可以进行程度不同的拆分。只要符合在标记为*的位置上的立体化学构型条件,则由特定的空间形式定义的可能的立体异构体,如对映异构体、非对映异构体、Z-和E-异构体均包括在式I中,并且可以采用常规方法从立体异构体的混合物中获得,或也可以通过与利用立体化学纯初始物质相结合的立体选择反应加以制备。
若存在各种官能团,本发明还包括任何酮和烯醇互变异构体形式及其混合物和盐。
立体异构体可通过光学拆分从在制备中获得的混合物中获得。同样可通过使用立体选择性反应且使用光学活性的起始原料和/或助剂来选择性地制备立体异构体。对于光学拆分而言,通常可以利用常规方法(参见Textbooks of Stereochemistry),例如用于将混合物拆分成非对映异构体的下述方法,例如物理方法,如结晶、层析法,尤其是柱层析和高压液相色谱法,视需要在减压下进行的蒸馏方法,萃取法和其它方法,通常采用在手性固相上的色谱分离,可以分离对映结构体的残余混合物。适用于制备量或用于工业规模的是这样的方法,例如结晶非对映盐,这可以利用光学活性酸从化合物中获得,并且若存在酸性基团,可以视需要利用光学活性碱。
所述的杂环取代的芳香类化合物的制备方法,包括以下步骤:
将通式II所示的化合物与通式III所示的化合物进行反应制得如通式I所示的化合物,其化学反应方程式如下:
其中,Hal代表卤素,优选Cl;取代基X1、X2、R1、R2、R3、R4、M1、M2、Q、Y和Z的定义如前所述;
优选地,所述反应在碱和溶剂的存在下进行;更优选地,所述碱选自含氮碱(如C1-C6烷基胺,优选三-(C1-C6)-烷基胺,例如三乙胺、三甲胺、N-乙基二异丙胺)中的至少一种;
所述溶剂选自芳香烃(如苯、氯苯、甲苯、甲酚或邻-、间-和对-二甲苯)、THF、DMF、DMA、甲醇、乙醇、乙腈、二氯乙烷、DMSO、Dioxane、二氯甲烷、甲苯或乙酸乙酯中的至少一种。
如通式II所示的化合物可参照WO12130798、WO1404882、WO14048882、WO18228985、WO18228986、WO19034602或WO19145245等所示方法制得。
一种除草剂组合物,其包括除草有效量的所述的杂环取代的芳香类化合物中的至少一种,优选地,还包括制剂助剂。
一种控制杂草的方法,其包括将除草有效量的所述的杂环取代的芳香类化合物中的至少
一种或所述的除草剂组合物使用在植物上或者杂草区域。
所述的杂环取代的芳香类化合物中的至少一种或所述的除草剂组合物在控制杂草上的用途,优选地,将所述的杂环取代的芳香类化合物用于防除有用作物中的杂草,所述有用作物为转基因作物或者基因组编辑技术处理过的作物。
对于许多经济上重要的单子叶和双子叶有害植物,本发明的式I化合物具有突出的除莠活性。本发明的活性物质也对于多年生杂草有效,这些杂草从根茎、根状茎、或其它的多年生的器官上生长出来,很难控制。关于这点,是否在播种前、萌发前或萌发后使用该物质一般不重要。特别提及本发明化合物可以控制的单子叶和双子叶杂草群的代表例子,没有限制到的确定的物种。活性物质有效作用的杂草物种的例子包括单子叶植物:一年生燕麦属、黑麦、草属、看麦娘属、法拉里斯、稗、马唐属、狗尾草属和莎草属,和多年生的冰草属、狗牙根属、白茅属和高粱属、以及多年生的莎草属。
关于双子叶杂草物种,其作用可以扩展到的物种例如一年生的猪殃殃属、堇菜属、婆婆纳属、野芝麻属、繁缕属、苋属、白芥属、番薯属、黄花稔属、母菊属和苘麻属,和多年生杂草旋花属、蓟属、酸模属和艾属。本发明活性物质在水稻播种这种待定条件下有效控制有害植物,例如稗、慈姑属、泽泻属、荸荠属、蔗草和莎草属。如果将本发明化合物在萌芽前施用于土壤表面,可以在杂草长出前完全预防杂草的秧苗,或在杂草长出子叶时就停止生长,最后在三到四星期之后完全死亡。本发明化合物特别抗下述植物的活性优良,阿皮拉草、小野芝麻、卷茎蓼、繁缕、长春藤叶婆婆纳、阿拉伯婆婆纳、三色堇和苋、猪殃殃属和地肤。
虽然本发明化合物对于单子叶和双子叶的杂草具有优良的除莠活性,但对于重要的经济类作物植物,例如小麦、大麦、黑麦、稻子、玉米、甜菜、棉花和大豆却根本没有损害,或者是损害是微不足道的。特别是和谷类作物相容得很好,例如小麦、大麦和玉米,特别是小麦。因此,本发明化合物非常适于有选择地控制在农用作物或观赏植物中的无用植物。
由于它们的除莠性质,在已知或将要出现的遗传工程的植物耕种中,这些活性物质可以用于控制有害植物。转基因植物通常具有优越的性状,例如对特定杀虫剂特别是特定除草剂的抵抗力,对植物病害或植物病害的致病微生物的抵抗力,例如特定的昆虫或真菌、细菌或病毒的微生物。其它的特别性状与产品的下述条件有关,例如,数量、质量、贮存稳定性、组分和特殊的成分。如此,已经知道获得的转基因植物产品具有增加的淀粉含量或改进的淀粉质量或不同的脂肪酸成份。
本发明的式I化合物或其盐优选用于,经济上重要的转基因的作物和观赏植物,例如谷类,例如小麦、大麦、黑麦、燕麦、粟、稻子、木薯和玉米、或用于甜菜、棉花、大豆、油菜籽、马铃薯、番茄、豌豆及其他蔬菜类植物的耕种。式I化合物优选用于有用植物耕种的除草剂,这些植物具有抗药性或通过遗传工程对除草剂的毒害作用具有抗药性。
传统的繁育具有比已知植物具有改进形状植物的方法包括,例如传统的交配方法和突变株繁育。换句话说,可以借助于遗传工程的方法(参见,例如EP-0221044 A,EP-0131624 A)来得到具有改进性状的新植物。例如,已经描述了几个方法:
-为了改进植物中的淀粉合成,利用遗传工程改变作物植物(例如WO 92/11376,WO 92/14827,WO 91/19806);
-对特定的除草剂具有抗性的转基因作物植物,对草丁膦除草剂(例如EP-0242236 A,EP-0242246 A)或对草甘膦类除草剂(WO 92/00377),或对磺酰脲类除草剂(EP-0257993 A,US-5013659 A);
-例如棉花的转基因作物植物,它能够产生苏芸金杆菌毒素(Bt毒素),这种毒素可以防御特定害虫对植物的侵害(EP-0142924 A,EP-0193259 A);
-具有改进的脂肪酸成份的转基因作物植物(WO91/13972)。
已经知道许多能够制备具有改进性状转基因植物分子生物技术(参见,例如Sambrook等,1989,分子扩增,实验手册第二版,美国冷泉港实验室出版,冷泉港,纽约;或Winnacker“Gene und Klone”[基因和克隆],VCH Weinheim,第二版1996或Christou,“植物科学的趋势”1(1996)423-431))。为了实现遗传工程的操作,可能将核酸分子引入质粒,通过DNA序列的重组,发生突变或序列改变。利用上述的标准方法,例如可以交换底物、除去部分序列或增加自然的或合成的序列。为了将DNA片段互相连接,有可能在片段上附带有结合体或连接体。
可以用下述方法制备降低活性的基因产品的植物细胞,例如通过表达至少一种适当的反义-RNA、正义-RNA来达到共抑制的效果,或通过表达至少一种适当构造的核糖酶,它特定裂解上述基因产品的转录产物。
为此目的,有可能使用包含基因产物全部编码序列的DNA分子,包括有可能存在的任何旁侧序列,和使用包含仅仅一部分编码序列的DNA分子,这些部分必须足够长以达到在细胞中反义的效果。也可以使用与基因产物编码序列具有高度同源性但不完全相同的序列。
当在植物中表达核酸分子时,合成的蛋白质可以在任何期望的植物细胞室中定位。然而为了在特定的室定位,有可能例如将编码区和DNA序列连接,以确保在特定位置定位。这些序列为本领域所属技术人员已知的(参见,例如Braun等,EMBO J.11(1992)3219-3227;Wolter等,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等Plant J.1(1991),95-106)。
利用已知的技术可以将转基因植物细胞重组到整个植物上。转基因植物可以为任何期望的植物品种,即单子叶和双子叶植物。用这样的方式,通过超表达、禁止或抑制同源(=自然的)基因或基因序列,或通过异种的(=外部的)基因或者基因序列的表达,有可能获得改进性状的转基因植物。
当在转基因的作物上使用本发明的活性物质时,除了具有在其它作物上可观察到的抑制有害植物的效果外,经常在相应的转基因作物上会有特殊的效果,例如可以改进或扩大控制杂草的范围,改进应用时的施用量,优选转基因作物的抗药性和除草剂的性能很好的结合,并且转基因的作物植物的生长和产率的影响。因此本发明也提供了所述化合物的用途,作为除草剂控制转基因作物植物中的有害植物。
另外本发明化合物可以明显调节作物植物的生长。通过调节参与植物代谢,使用这些化合物定向控制植物的组分和促进收获,例如使植物干化和矮化生长。而且它们也适于调节和抑制不希望的植物生长,而不破坏作物的生长。抑制植物的生长在许多单子叶植物和双子叶植物作物中起着非常重要的作用,因为这样可以减少或完全预防倒伏。
可以使用一般的制剂来应用本发明的化合物,可使用可湿性粉剂、浓缩乳剂、可喷洒的溶液、粉末或颗粒。这样本发明也提供了包括式I化合物的除草剂组合物。根据通常的生物学和/或化学的物理参数,可以用多种方式配制式I化合物。适合的制剂选择实例为:可湿性粉剂(WP)、水溶性的粉末(SP)、水溶性的浓缩物、浓缩乳剂(EC)、例如油在水中分散和水在油中分散的乳剂(EW)、可喷洒溶液、悬浮剂浓缩物(SC)、可分散油悬浮剂(OD)、以油或水为稀释剂的悬浮液、可混溶油的溶液、粉末(DP)、胶囊悬浮液(CS)、包核(seeddressing)组合物、用于撒播和土壤施药的颗粒、喷射颗粒、涂覆颗粒和吸收颗粒,水中可分散的颗粒(WG)、水溶性的颗粒(SG)、ULV(超低容量)配方、微囊和蜡制品。这些单个的制剂类型为已知的,在下述文献中有描述,例如Winnacker-Küchler,“Chemische Techonologie”[化学工艺],第7卷,C.Hauser Verlag Munich,第4版1986;Wade van Valkenburg,“Pesticide Formulations”,Marcel Dekker,N.Y.,1973;K.Martens,“Spray Drying”手册,第3版1979,G.Goodwin Ltd.London。
必要的制剂助剂,例如惰性物质、表面活性剂、溶剂及其它添加剂同样为已知的,并在下述文件中描述,例如Watkins的“粉末稀释剂杀虫剂和载体手册”,第二版,Darland书Caldwell N.J.;H.v.01phen“粘土胶体化学的入门”,第二版,J.Wiley和Sons,N.Y.;C.Marsden的“溶剂指南”第二版,Interscience,N.Y.1963;McCutcheon的“洗涤剂和乳化剂年报”,MC发行公司,Ridgewood N.J.;Sisley和Wood,“表面活性剂百科全书”,化学出版公司,N.Y.1964;的[环氧乙烷加成物表面活性剂],Wiss.Verlagagesell.Stuttgart 1976;Winnacker-Küchler的“Chemische Technologie”[化学工艺],第7卷,C.Hauser Verlag Munich,第4版1986。
可湿性粉剂能均匀地可分散在水中,除了活性物质,还包括稀释剂或惰性物质、离子和非离子型表面活性剂(润湿剂、分散剂),例如聚乙氧基烷基酚、聚乙氧基脂肪醇、聚氧乙基脂肪族胺、脂肪醇聚二醇醚硫酸盐、烷基磺酸盐、烷基苯基磺酸盐、木质磺酸钠、2,2’-二萘甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰甲基牛磺酸钠。为了制备可湿性粉剂,将除草剂的活性物质细磨,例如使用常用的仪器,如用锤磨机、风扇磨碎机和喷气式磨碎机,同时或顺序混入助剂。
将活性物质溶解在有机溶剂中制备浓缩乳剂,溶剂例如丁醇、环己酮、二甲基甲酰胺、二甲苯或较高沸点的芳族化合物或碳氢化合物或溶剂的混合物,并再加入一种或多种离子的和/或非离子型表面活性剂(乳化剂)。可以使用的乳化剂的例子为例如十二烷基苯磺酸钙的烷基芳基磺酸钙,或非离子乳化剂,例如脂肪酸聚二醇酯、烷基芳香基聚二醇醚、脂肪醇聚二醇醚、氧化丙烯-环氧乙烷缩合产物、烷基聚醚、例如山梨糖醇酐脂肪酸酯的山梨聚糖酯,或例如聚氧化乙烯山梨糖醇酐脂肪酯的聚氧化乙烯山梨聚糖酯。
将活性物质和细碎的固态物质研磨得到粉末,固态物质例如滑石、如高岭土、皂土和叶蜡石的天然粘土、或硅藻土。以水或油为基底的悬浮液可以通过下述方法制备,例如利用商业上通用的玻珠研磨机进行湿磨,加入或不加入上述另一个制剂类型的表面活性剂。
制备例如水包油乳化剂(EW)的乳剂,可以使用含水的有机溶剂,使用搅拌器、胶体研磨器和/或静态混合器,如果需要,加入如上所述另一个制剂类型的表面活性剂。
用下述方法制备颗粒剂,将活性物质喷到吸附物上,使用惰性物料颗粒化,或将活性物质浓缩到例如沙、高岭石载体的表面,通过粘合剂将惰性物料粒化,粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。可以用制备肥料颗粒剂的方法将合适的活性物质粒化,如果需要可以混有肥料。使用通常的方法制备水悬浮颗粒剂,例如喷洒-干燥,流化床造粒、磨盘造粒、使用高速混合机混合,并在无固体惰性物料的情况下挤压。
关于使用磨盘、流化床、挤压机和喷涂颗粒剂的制备方法,参见下述工艺,例如“Spray Drying手册”第三版1979,G.Goodwin有限公司,伦敦;J.E.Browning,“Agglomeration”,化学和工程1967,147ff页;“Perry’s化学的工程师手册”,第五版,McGraw-Hill,纽约1973,8-57页。如果要知道关于作物保护产品的制剂,参见例如,G.C.Klingman,“Weed Control as a Science”,John Wiley和Sons公司,纽约,1961 81-96页和J.D.Freyer,S.A.Evans“杂草防除手册”,第五版,Blackwell Scientific Rublications,牛津大学1968,101-103页。
农用化学品制剂通常包含按重量计0.1到99%,特别是0.1到95%的活性物质式I。可湿性粉剂中活性物质的浓度为,按重量计例如从大约10到99%,通常的制剂组分构成按重量计剩余量到100%。活性物质在浓缩乳剂中的浓度按重量计可以为大约1到90%,优选5到80%。粉末制剂包含按重量计1到30%的活性物质,通常优选按重量计5到20%的活性物质,然而可喷洒的溶液包含按重量计大约0.05到80%,优选2到50%的活性物质。关于水悬浮颗粒剂中活性物质的含量,主要根据活性物质为液体还是固态,和造粒时使用的助剂、填料等等。水悬浮颗粒剂中活性物质的含量例如按重量计在1到95%之间,优选按重量计在10到80%之间。
另外所述的活性物质的制剂可以包括增粘剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、防冻剂、溶剂、填料、载体、着色剂、消泡剂、蒸发抑制剂和通常在所有情况下都常用的pH和粘度调节剂。
以这些制剂为基础,也可能和其他杀虫剂活性物质例如杀虫剂、杀螨剂、除草剂和杀菌剂混合,也可以和安全剂、肥料和/或植物生长调节剂混合,混合方式可以为预先混合好的或灌装混合。
在混配制剂或桶混制剂中,可以和本发明的活性物质混合的合适的活性物质为,例如《世界农药新品种技术大全》,中国农业科学技术出版社,2010.9和这里引用的文献中的已知物质。例如以下提到的除草剂活性物质可以和式I混合物混合,(备注:化合物的名称,或者为根据国际标准化组织(ISO)的普通名称,或者为化学名称,适当的时候有代号):乙草胺、丁草胺、甲草胺、异丙草胺、异丙甲草胺、精异丙甲草胺、丙草胺、毒草胺、克草胺、萘丙酰草胺、R-左旋萘丙酰草胺、敌稗、苯噻酰草胺、双苯酰草胺、吡氟酰草胺、杀草胺、氟丁酰草胺、溴丁酰草胺、二甲噻草胺、高效二甲噻草胺、乙氧苯草胺、氟噻草胺、甲氧噻草胺、吡草胺、异恶草胺、高效麦草伏甲酯、高效麦草伏丙酯、二丙烯草胺、烯草胺、丁酰草胺、环丙草胺、氟磺酰草胺、庚酰草胺、异丁草胺、丙炔草胺、特丁草胺、二甲苯草胺、二甲草胺、落草胺、三甲环草胺、氯甲酰草胺、炔苯酰草胺、戊酰苯草胺、卡草胺、新燕灵、三环赛草胺、丁烯草胺、牧草胺、苄草胺、醌萍胺、苯氟磺胺、萘丙胺、乙酰甲草胺、萘草胺、噻草胺、吡氰草胺、苯草多克死、草克乐、氯酞亚胺、丁脒胺、氟吡草胺、莠去津、西
玛津、扑草净、氰草净、西草净、莠灭净、扑灭津、异丙净、氟草净、特丁净、特丁津、三嗪氟草胺、环丙津、甘扑津、草达津、扑灭通、西玛通、叠氮净、敌草净、异戊乙净、环丙青津、灭莠津、另丁津、仲丁通、特丁通、甲氧丙净、氰草净、抑草津、可乐津、莠去通、灭草通、甘草津、三聚氰酸、Indaziflam、绿磺隆、甲磺隆、苄嘧磺隆、氯嘧黄隆、苯磺隆、噻磺隆、吡嘧黄隆、甲基二磺隆、甲基碘磺隆钠盐、甲酰氨基嘧磺隆、醚磺隆、醚苯磺隆、甲嘧磺隆、烟嘧磺隆、胺苯磺隆、酰嘧磺隆、乙氧嘧磺隆、环丙嘧磺隆、砜嘧磺隆、四唑嘧磺隆、啶嘧黄隆、单嘧磺隆、单嘧磺酯、氟唑磺隆、氟啶嘧磺隆、氟吡嘧磺隆、环氧嘧磺隆、唑吡嘧磺隆、氟嘧磺隆、丙苯磺隆、三氟丙磺隆、磺酰磺隆、三氟啶磺隆、氟胺磺隆、三氟甲磺隆、甲磺隆钠盐、氟吡磺隆、甲硫嘧磺隆、嘧苯胺磺隆、Propyrisulfuron(丙嗪嘧磺隆)、嗪吡嘧磺隆、三氟羧草醚、氟磺胺草醚、乳氟禾草灵、乙羧氟草醚、乙氧氟草醚、草枯醚、苯草醚、氯氟草醚乙酯、甲羧除草醚、三氟甲草醚、甲氧除草醚、三氟硝草醚、氟化除草醚、氟呋草醚、除草醚、甲草醚、二甲草醚、氟酯肟草醚、氟草醚酯、Halosafen、绿麦隆、异丙隆、利谷隆、敌草隆、莎扑隆、氟草隆、苯噻隆、甲基苯噻隆、苄草隆、磺噻隆、异恶隆、特丁噻草隆、炔草隆、氯溴隆、甲基杀草隆、酰草隆、甲氧杀草隆、溴谷隆、甲氧隆、绿谷隆、灭草隆、环草隆、非草隆、氟硫隆、草不隆、枯草隆、草完隆、异草完隆、环莠隆、噻氟隆、丁噻隆、枯莠隆、对氟隆、甲胺噻唑隆、隆草特、三甲异脲、恶唑隆、Monisouron、Anisuron、Methiuron、Chloreturon、四氟隆、甜菜宁、甜菜宁-乙酯、甜菜安、磺草灵、特草灵、燕麦灵、苯胺灵、氯苯胺灵、二氯苄草酯、灭草灵、氯炔灵、Carboxazole、Chlorprocarb、Fenasulam、BCPC、CPPC、Carbasulam、丁草特、禾草丹、灭草猛、禾草特、野麦畏、哌草丹、禾草畏、稗草丹、环草敌、燕麦敌、菌达灭、乙硫草特、坪草丹、克草猛、苄草丹、仲草丹、硫烯草丹、草灭散、Isopolinate、Methiobencarb、2,4-滴丁酯、2甲4氯钠、2,4-滴异辛酯、2甲4氯异辛酯、2,4-滴钠盐、2,4-滴二甲胺盐、2甲4氯乙硫酯、2甲4氯、2,4-滴丙酸、高2,4-滴丙酸盐、2,4-滴丁酸、2甲4氯丙酸、2甲4氯丙酸盐、2甲4氯丁酸、2,4,5-涕、2,4,5-涕丙酸、2,4,5-涕丁酸、2甲4氯胺盐、麦草畏、抑草蓬、伐草克、赛松、三氯苯酸、氨二氯苯酸、甲氧三氯苯酸、禾草灵、吡氟禾草灵、精吡氟禾草灵、氟吡甲禾灵、高效吡氟氯禾灵、喹禾灵、精喹禾灵、恶唑禾草灵、精恶唑禾草灵、喔草酯、氰氟草酯、恶唑酰草胺、炔草酯、噻唑禾草灵、炔禾灵、羟戊禾灵、三氟禾草肟、异恶草醚、百草枯、敌草快、安磺灵、乙丁烯氟灵、异丙乐灵、甲磺乐灵、环丙氟灵、氨基丙氟灵、乙丁氟灵、氯乙氟灵、氨基乙氟灵、地乐灵、氯乙地乐灵、Methalpropalin、丙硝酚、草甘膦、莎稗膦、草铵膦、甲基胺草磷、草硫膦、哌草膦、双丙氨膦、地散磷、抑草磷、蔓草磷、伐垅磷、双甲胺草磷、草特磷、咪唑烟酸、咪唑乙烟酸、咪唑喹啉酸、甲氧咪草烟、甲氧咪草烟铵盐、甲咪唑烟酸、咪草酯、氯氟吡氧乙酸、氯氟吡氧乙酸异辛酯、二氯吡啶酸、氨氯吡啶酸、三氯吡氧乙酸、氟硫草定、卤草定、三氯吡啶酚、噻草啶、氟啶草酮、氯氨吡啶酸、氟吡草腙、三氯吡氧乙酸丁氧基乙酯、Cliodinate、稀禾啶、烯草酮、噻草酮、禾草灭、环苯草酮、丁苯草酮、肟草酮、吡喃草酮、Buthidazole、嗪草酮、环嗪酮、苯嗪草酮、乙嗪草酮、Ametridione、Amibuzin、溴苯腈、辛酰溴苯腈、辛酰碘苯腈、碘苯腈、敌草腈、二苯乙腈、双唑草腈、羟敌草腈、Iodobonil、唑嘧磺草胺、双氟磺草胺、五氟磺草胺、磺草唑胺、氯酯磺草胺、双氯磺草胺、啶磺草胺、
氟草黄、双草醚、嘧啶肟草醚、环酯草醚、嘧草醚、嘧硫草醚、双环磺草酮、硝磺草酮、磺草酮、Tembotrione、Tefuryltrione、Bicyclopyrone、Ketodpiradox、异恶唑草酮、异恶氯草酮、Fenoxasulfone、Methiozolin、异丙吡草酯、吡草醚、吡唑特、野燕枯、苄草唑、吡草酮、吡氯草胺、Pyrasulfotole、苯唑草酮、Pyroxasulfone、唑草胺、氟胺草唑、杀草强、胺唑草酮、唑啶草酮、氟唑草酮、甲磺草胺、Bencarbazone、双苯嘧草酮、氟丙嘧草酯、除草定、异草定、环草啶、特草定、Flupropacil、吲哚酮草酯、氟烯草酸、丙炔氟草胺、炔草胺、酞苄醚、Flumezin、五氯酚(钠)、地乐酚、特乐酚、特乐酯、戊硝酚、二硝酚、氯硝酚、地乐施、地乐特、丙炔恶草酮、恶草酮、环戊恶草酮、氟唑草胺、嗪草酸甲酯、四唑酰草胺、氟哒嗪草酯、杀草敏、溴莠敏、二甲达草伏、哒草醚、草哒酮、草哒松、哒草伏、Pyridafol、二氯喹啉酸、氯甲喹啉酸、苯达松、哒草特、恶嗪草酮、草除灵、异恶草酮、环庚草醚、异丙酯草醚、丙酯草醚、茚草酮、氯酸钠、茅草枯、三氯醋酸、一氯醋酸、六氯丙酮、四氟丙酸、牧草快、溴酚肟、三唑磺、灭杀唑、呋草酮、呋草磺、乙呋草磺、嘧草胺、氯酞酸、氟咯草酮、稗草稀、丙烯醛、苯草灭、灭草环、燕麦酯、噻二唑草胺、棉胺宁、羟草酮、甲氧苯酮、苯嘧磺草胺、氯酰草膦、三氯丙酸、Alorac、Diethamquat、Etnipromid、Iprymidam、Ipfencarbazone、Thiencarbazone-methyl、Pyrimisulfan、Chlorflurazole、Tripropindan、Sulglycapin、甲硫磺乐灵、Cambendichlor、环丙嘧啶酸、硫氰苯胺、解草酮、解草啶、解草安、解草唑、解草喹、解草腈、解草烷、解草胺腈、解草烯、吡唑解草酯、呋喃解草唑、肟草安、双苯噁唑酸、二氯丙烯胺、氟氯吡啶酯、DOW氯氟吡啶酯、UBH-509、D489,LS82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0744、DOWCO535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127和KIH-2023。
当使用时,如果需要,将市售的制剂以常见的方式稀释,例如在可湿性粉剂、浓缩乳剂、悬浮液和在水中悬浮的颗粒时,使用水稀释。粉末、土壤施药所用的颗粒剂或撒播和喷洒的溶液,一般在使用前不需要进一步用惰性物质稀释。随着外部条件的变化,要求的式I化合物的使用量也不同,外部条件为,例如温度、湿度、使用的除草剂的性质等等。它可以有大的变化幅度,例如在0.001到1.0kg a.i./ha之间,或更多的活性物质,但优选在0.005到750g
a.i./ha之间,特别是在0.005到250g a.i./ha之间。
以下实施例用于举例说明本发明,不应当视其为以任何方式限制本发明。本发明要求保护的权利范围通过权利要求书进行说明。
鉴于化合物的经济性与多样性,我们优选合成了一些化合物,在合成的诸多化合物中,选取部分列于下表1中。具体的化合物结构及相应的化合物信息如表1-2所示。表1中的化合物只是为了更好的说明本发明,但并不限定本发明,对于本领域的技术人员而言,不应将此理解为本发明上述主题的范围仅限于以下化合物。
表1化合物结构
表2化合物1HNMR
制备本发明化合物的数种方法详解说明于以下方案和实施例中。原料可以经市场购买到或者可以通过文献中已知的方法或者如详解所示进行制备。本领域技术人员应当理解,也可以利用其它合成路线合成本发明的化合物。尽管在下文中已经对合成路线中的具体原料和条件进行了说明,但是,可以很容易地将其替换为其它类似的原料及条件,这些对本发明制备方法的变型或者变体而产生的诸如化合物的各种异构等都包括在本发明范围内。另外,如下所述制备方法可以按照本发明公开内容、使用本领域技术人员熟知的常规化学方法进行进一步修饰。例如,在反应过程中对适当的基团进行保护等等。
以下提供的方法实施例用于促进对本发明的制备方法的进一步了解,使用的具体物质、种类和条件确定为是对本发明的进一步说明,并不是对其合理范围的限制。在下表中表明的合成化合物中使用的试剂或者可以市场购买到,或者可以由本领域普通技术人员轻易制备得到。
代表性化合物的实施例如下,其他化合物的合成方法类似,此处不再详细说明。
1、化合物10的合成
(1)将化合物10-1(52.3g,0.21mmol),乙二醇(25.6g,0.42mol),对甲苯磺酸(3.4g,0.02mol)溶解在甲苯(500ml)中,120℃反应8h,液相检测原料消耗完毕,冷却后浓缩,加水,EA萃取三次,饱和食盐水洗三次,有机相干燥浓缩得到粗产物,粗品拌样过柱,得到化合物10-2(55.2g,0.18mol),收率85%。
(2)将化合物10-2(55.2g,0.18mol)溶解在500mL乙醇和100mL水中,加入铁粉(50g,0.9mol),NH4Cl(19g,0.36mmol),升温至60度反应2小时,液相检测反
应结束。反应液降温,垫硅藻土抽滤,母液浓缩得粗品,加入乙酸乙酯和水洗,分液,有机相浓缩得粗品,拌样过柱,得到10-3(30g,0.11mol),收率61%。
(3)将化合物10-3(10g,38mmol)溶解在200mL乙腈中,加入联频哪醇硼酸酯10-4(48g,1.90mol),然后缓慢滴加亚硝酸叔丁酯(7.8g,76mmol),升温至60度反应12h,液相检测原料消失,反应液浓缩得粗品,加水加乙酸乙酯萃取,有机相干燥浓缩,拌样过柱得到化合物10-5(5.5g,14.7mmol),收率39%。
(4)将10-6(0.4g,1.86mmol)、硼酯10-5(1.04g,2.80mmol)和碳酸钾(0.78g,5.6mmol)加入干净的烧瓶中,再加入1,4-dioxane 20ml和水2ml,再氮气保护抽气2-3次,抽气完毕加入1,1'-双(二苯基膦)二茂铁]二氯化钯二氯甲烷络合物(44.74mg,54.79umol),再次抽气,升温至100℃过夜,中控反应完成后,后处理减压蒸馏拉干溶剂,加水洗涤,EA萃取2-3次,再将EA相用饱和食盐水洗涤2-3次,在EA相中加入无水硫酸钠干燥,加入硅胶拌样过柱,正相纯化,得到10-7(600mg,1.42mmol)。
(5)将10-7(0.6g,1.42mmol)、盐酸羟胺(0.48g,7.1mmol)加入干净的烧瓶中,加入乙醇和水混合溶剂(10ml:2ml),80摄氏度下搅拌3小时,中控反应完成后,直接拌样,正向纯化,得到10-8(540mg,1.36mmol)。
(6)将10-8(0.54g,1.36mmol)、NCS(0.36g,2.72mmol)加入干净的烧瓶中,加入10ml DMF溶解,40摄氏度下搅拌3小时,中控反应完成后,加入水洗再加EA萃取(适量EA萃取3次),再将EA相用适量饱和食盐水洗两遍,旋干得到白色固体10-9(580mg,1.35mmol)。
(7)将10-9(0.8g,0.69mmol)和三乙胺(0.14g,1.38mmol)溶于DCM中,冰浴下滴加10-10(0.2g,0.46mmol)的二氯甲烷溶液,滴加完毕,撤冰水浴室温过夜。中控反应完成后,直接拌样,正向纯化得到化合物10(70mg,0.14mmol)。
2、化合物104的合成
(1)在100mL单口瓶中加入104-1(2g,10.62mmol,1.0eq),加入16mL的1,4二氧六环和4mL的水,氟化铯(3.23g,21.23mmol,2.0eq),加入104-2(2.99g,15.92mmol,1.5eq)以及催化量的Pd(dppf)Cl2(0.087g,0.096mmol,0.01eq),加入完毕后氩气置换3次,反应液在100℃条件下搅拌过夜。LCMS检测原料基本反应完全,有一个主要的新峰生成。将反应液旋蒸掉大部分溶剂,加入水100mL和乙酸乙酯(100mL*3)萃取,有机相用饱和食盐水洗涤(100mL*3),有机相浓缩后拌样过柱,得到104-3(2.5g,80%收率,淡黄色固体)。
(2)在100mL单口瓶中依次加入104-3(2.5g,8.44mmol,1.0eq),AIBN(0.45g,2.72mmol,0.2eq),NBS(2.25g,12.66mmol,1.5eq),30mL乙腈,然后氩气置换3次,反应液在80℃条件下搅拌过夜。LCMS检测原料基本反应完全,有一个主要的新峰生成。将反应液旋蒸掉大部分溶剂,加入水20mL和乙酸乙酯(50mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-4(2.3g,粗品,黄色固体),粗品直接投入到下一步。
(3)在100mL单口瓶中依次加入104-4(2.3g,6.13mmol,1.0eq),N-甲基吗啉氧化物(1.44g,12.23mmol,2eq),30mL乙腈,反应液在室温条件下搅拌过夜。LCMS检测原料基本反应完全,有一个主要的新峰生成。将反应液旋蒸掉大部分溶剂,加入水20mL和乙酸乙酯(50mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-5(1.5g,粗品,黄色固体),粗品直接投入到下一步。
(4)在100mL单口瓶中依次加入104-5(1.5g,4.84mmol,1.0eq),盐酸羟胺(0.34g,4.84mmol,1eq),25mL乙醇,反应液在室温条件下搅拌三个小时。LCMS检测原料基本反应完全,有一个主要的新峰生成。将反应液旋蒸掉溶剂,加入水20mL和乙酸乙酯(50mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-6(1.2g,粗品,淡黄色固体),粗品直接投入到下一步。
(5)在100mL单口瓶中依次加入104-6(1.2g,3.69mmol,1.0eq),NCS(0.52g,3.87mmol,1.05eq),20mL DMF,反应液在室温条件下搅拌三个小时。LCMS检测原料基本反应完全,有一个主要的新峰生成。加入水100mL和乙酸乙酯(100mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-7(0.9g,粗品,黄色固体),粗品直接投入到下一步。
(6)25℃下,在100mL单口瓶中依次加入甲基丙烯酸乙酯(0.75g,7.51mmol,3eq),加入三乙胺(0.25g,2.5mmol,1eq),15mL二氯甲烷,滴加化合物104-7(0.9g,2.5mmol,1eq)的二氯甲烷溶液,室温下搅拌5小时。LCMS检测原料基本反应完全,有一个主要的新峰生成。加入水(100mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-8(0.7g,粗品,黄色油状物),粗品直接投入到下一步。
(7)25℃下,在100mL单口瓶中依次加入化合物104-8(0.8g,1.89mmol,1eq),氢氧化锂(0.14g,5.7mmol,3eq),15mL THF和5mL水,室温下搅拌5小时。LCMS检测原料基本反应完全,有一个主要的新峰生成。pH调到弱酸性,加入水100mL和乙酸乙酯(100mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后得到粗品104-9(0.7g,粗品,黄色油状物),粗品直接投入到下一步。
(8)在100mL单口瓶中依次加入104-9(0.1g,0.24mmol,1.0eq),氯甲基甲硫醚(0.047g,0.49mmol,2eq),无水碳酸钾(0.1g,0.74mmol,3.0eq),10mL DMF,45℃下反应3小时。LCMS检测原料基本反应完全,有一个主要的新峰生成。加入水20mL和乙酸乙酯(20mL*3)萃取,有机相用饱和食盐水洗涤(20mL*3),有机相浓缩后拌样过柱,得到化合物104(0.05g,44%收率,无色油状物)。
生物活性评价:
植物破坏(即生长控制率)的活性级别标准如下:
10级:完全死亡;
9级:生长控制率大于等于90%且小于100%;
8级:生长控制率大于等于80%且小于90%;
7级:生长控制率大于等于70%且小于80%;
6级:生长控制率大于等于60%且小于70%;
5级:生长控制率大于等于50%且小于60%;
4级:生长控制率大于等于40%且小于50%;
3级:生长控制率大于等于30%且小于40%;
2级:生长控制率大于等于20%且小于30%;
1级:生长控制率小于20%;
0级:无效果。
以上生长控制率为鲜重控制率。
苗后测试实验:
将单子叶和双子叶杂草种子(播娘蒿、荠菜、苘麻、猪殃殃、繁缕、麦家公、蔊菜、看麦娘、日本看麦娘、牛筋草、菵草、硬草、小飞蓬、蜡烛草、婆婆纳、雀麦、节节麦、虉草、反枝苋、藜、鸭跖草、苣荬菜、田旋花、刺儿菜、龙葵、铁苋菜、马唐、稗草、绿狗尾草、金狗尾草、千金子、鸭舌草、野慈姑、萤蔺、香附子、碎米莎草、异型莎草、飘拂草、马齿苋、苍耳、牵牛、白酒草等)以及主要作物种子(小麦、玉米、水稻、大豆、棉花、油菜、谷子、高粱、马铃薯、芝麻、蓖麻等)放置在装有土壤的塑料盆中,然后覆盖0.5-2厘米土壤,使其在良好的温室环境中生长,播种2周后在2-3叶期处理测试植物,分别将供试的本发明化合物用丙酮溶解,然后加入吐温80,以1.5升/公顷油酸甲酯的乳油作为增效剂,用一定的水稀释成一定浓度的溶液,用喷雾塔喷施到植物上。施药后在温室中培养3周后统计杂草的实验效果,所用化合物计量为500,250,125,60,15,7.5g a.i./ha,重复三次,取平均值。代表性数据列于表3。
表3苗后杂草试验结果
苗前测试实验:
将单子叶和双子叶杂草种子以及主要作物种子(小麦、玉米、水稻、大豆、棉花、油菜、谷子、高粱)放置在装有土壤的塑料盆中,然后覆盖0.5-2厘米土壤,分别将供试的本发明化合物用丙酮溶解,然后加入吐温80,用一定的水稀释成一定浓度的溶液,播种后立即喷施。施药后在温室中培养4周后观察实验结果,发现本发明的药剂多数在250g a.i./ha计量下效果出众,尤其对稗草、马唐、苘麻等杂草,且很多化合物对玉米、小麦、水稻、大豆、有良好的选择性。
同时,我们经过小麦田和水稻田主要杂草测试发现,本发明所述化合物普遍具有较好的杂草防效,尤其是我们注意到对于ALS抑制剂有抗性的野慈姑、萤蔺、异型莎草、播娘蒿、荠菜、麦家公、猪殃殃、香附子等阔叶杂草和莎草有极高的活性,具有非常好的商业价值。
同时经过很多测试发现,本发明所述化合物及其组合物很多对结缕草、狗牙根、高羊茅、早熟禾、黑麦草、海滨雀稗等禾本科草坪有很好的选择性,能防除很多关键禾本科杂草以及阔叶杂草。对不同施药方式下的甘蔗、大豆、棉花、油葵、马铃薯、果树、蔬菜等测试也显示出极好的选择性和商业价值。
Claims (10)
- 一种杂环取代的芳香类化合物,如通式I所示:
其中,Y代表卤素、卤代烷基、氰基、硝基或氨基;Z代表氢、卤素或羟基;M1、M2分别独立地代表CR5或N(O)m;Q代表CX3X4;R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基烷基、硝基、氰基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,所述“烷基”、“烯基”、“炔基”、“环烷基”、“环烷基烷基”、“环烯基”或“环烯基烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的;X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基烷基、芳基、芳基烷基、氨基、氨基烷基、氨基羰基烷基、氨基羰基氧基烷基、氨基硫代羰基氧基烷基、氨基磺酰基或氨基磺酰基氧基烷基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-烷基-(CO)OH或-O-烷基-(CO)OR”中的至少一个基团所取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“氨基”、“氨基烷基”、“氨基羰基烷基”、“氨基羰基氧基烷基”、“氨基硫代羰基氧基烷基”、“氨基磺酰基”或“氨基磺酰基氧基烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-烷基-(CO)OR11、-(SO2)R11、-(SO2)OR11、-烷基-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;R’分别独立地代表氢、卤素、烷氧基、烷氧基烷基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、杂环基或杂环基烷基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“杂环基”或“杂环基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;R”分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、芳基烯基、杂环基、杂环基烷基或杂环基烯基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、三烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的至少一个基团所取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“芳基烯基”、“杂环基”、“杂环基烷基”或“杂环基烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;W1代表O、S或NW4;W2代表OW3、SW3或NW4W5;W3分别独立地代表氢、烷基、烯基、炔基、环烷基、环烯基、杂环基、芳基、 其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、环烷基、三烷基甲硅烷基、环烯基、杂环基、芳基、 中的至少一个基团所取代的,所述“环烷基”、“环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;W4、W5分别独立地代表氢、烷基、烯基、炔基、环烷基、环烯基、杂环基、芳基、 其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、环烷基、三烷基甲硅烷基、环烯基、杂环基、芳基、 中的至少一个基团所取代的,所述“环烷基”、“环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;或者NW4W5代表或者未取代或取代的1-位为氮原子的杂环基;X11分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、杂环基、杂环基烷基、芳基或芳基烷基,其中,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X12分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、杂环基、杂环基烷基、芳基或芳基烷基,其中,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“杂环基”、“杂环基烷基”、“芳基”或“芳基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X13、X14分别独立地代表氢、卤素、氰基、烷氧基、烷氧基烷基、烷基羰基、烷氧基羰基、烷基磺酰基、烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、芳基、芳基烷基、杂环基或杂环基烷基,或者基团CX13X14一起形成未取代或取代的环状结构,或者基团NX13X14一起形成未取代或取代的1-位为氮原子的杂环基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“环烷基”、“环烷基烷基”、“环烯基”、“环烯基烷基”、“芳基”、“芳基烷基”、“杂环基”或“杂环基烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、烷基、烯基、炔基、环烷基、卤代烷基、卤代烯基、卤代炔基、卤代环烷基、被烷基取代的环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-烷基-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所 取代的-OCH2CH2-或-OCH2O-形成稠环;R11分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、环烯基烷基、苯基或苄基,其中,所述“烷基”、“烯基”或“炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的;R12分别独立地代表氢、烷基、烯基、炔基、烷氧基、烷基磺酰基、环烷基、环烷基烷基、环烯基或环烯基烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表未取代或取代的1-位为氮原子的杂环基;R13分别独立地代表烷基、烯基、炔基、环烷基、苯基或被选自以下至少一个基团所取代的苯基:卤素,氰基,硝基,烷基,卤代烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基磺酰基或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基或卤代烷氧基中的至少一个基团所取代的苯氧基;R14分别独立地代表氢,烷基,卤代烷基,苯基或被选自卤素、氰基、硝基、烷基、卤代烷基、烷氧基羰基、烷硫基、烷基磺酰基、烷氧基或卤代烷氧基中的至少一个基团所取代的苯基;m代表0或1。 - 根据权利要求1所述的一种杂环取代的芳香类化合物,其特征在于,Y代表卤素、卤代C1-C8烷基、氰基、硝基或氨基;优选地,Y代表卤素、卤代C1-C6烷基、氰基、硝基或氨基。
- 根据权利要求1或2所述的一种杂环取代的芳香类化合物,其特征在于,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C8烷基、硝基、氰基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,所述“C1-C8烷基”、“C2-C8烯基”、“C2-C8炔基”、“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”或“C3-C8环烯基C1-C8烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的;优选地,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C6烷基、硝基、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”、“C2-C6炔基”、“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”或“C3-C6环烯基C1-C6烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤 代C1-C6烷氧基中的1、2或3个基团所取代的;更优选地,R1、R2、R3、R4、R5分别独立地代表氢、卤素、羟基、巯基、甲酰基、羟基C1-C6烷基、硝基、氰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、-OR11、-SR11、-(SO)R11、-(SO2)R11、-(SO2)OR11、-O(SO2)R11、-N(R12)2、苯基或苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”、“C2-C6炔基”、“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”或“C3-C6环烯基C1-C3烷基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的。
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根据权利要求1-3任意一项所述的一种杂环取代的芳香类化合物,其特征在于,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C8烷基、芳基、芳基C1-C8烷基、氨基、氨基C1-C8烷基、氨基羰基C1-C8烷基、氨基羰基氧基C1-C8烷基、氨基硫代羰基氧基C1-C8烷基、氨基磺酰基或氨基磺酰基氧基C1-C8烷基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C8烷基)-(CO)OH或-O-(C1-C8烷基)-(CO)OR”中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“氨基”、“氨基C1-C8烷基”、“氨基羰基C1-C8烷基”、“氨基羰基氧基C1-C8烷基”、“氨基硫代羰基氧基C1-C8烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C8烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C8烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C8烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;R’分别独立地代表氢、卤素、C1-C8烷氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷基、 C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、杂环基或杂环基C1-C8烷基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“杂环基”或“杂环基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;R”分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、芳基C2-C8烯基、杂环基、杂环基C1-C8烷基或杂环基C2-C8烯基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C8烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“芳基C2-C8烯基”、“杂环基”、“杂环基C1-C8烷基”或“杂环基C2-C8烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;优选地,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C6烷基、芳基、芳基C1-C6烷基、氨基、氨基C1-C6烷基、氨基羰基C1-C6烷基、氨基羰基氧基C1-C6烷基、氨基硫代羰基氧基C1-C6烷基、氨基磺酰基或氨基磺酰基氧基C1-C6烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C6烷基)-(CO)OH或-O-(C1-C6烷基)-(CO)OR”中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基 C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“氨基”、“氨基C1-C6烷基”、“氨基羰基C1-C6烷基”、“氨基羰基氧基C1-C6烷基”、“氨基硫代羰基氧基C1-C6烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C6烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C6烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C6烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;R’分别独立地代表氢、卤素、C1-C6烷氧基、C1-C6烷氧基C1-C6烷基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、杂环基或杂环基C1-C6烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“杂环基”或“杂环基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;R”分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、芳基C2-C6烯基、杂环基、杂环基C1-C6烷基或杂环基C2-C6烯基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C6烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“芳基C2-C6烯基”、“杂环基”、“杂环基C1-C6烷基”或“杂环基C2-C6烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;更优选地,X1、X2、X3、X4分别独立地代表氢、卤素、硝基、氰基、氰硫基、羟基、巯基、磺酸基、甲酰基、卤代甲酰基、叠氮基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6 环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、-PO(OR’)2、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO2)R”、-Si(R”)3、-O(CO)R”、-O-(SO2)R”、-S(CO)R”、-(SO2)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’=N-OH、-CR’=N-O-R”、杂环基、杂环基C1-C3烷基、芳基、芳基C1-C3烷基、氨基、氨基C1-C3烷基、氨基羰基C1-C3烷基、氨基羰基氧基C1-C3烷基、氨基硫代羰基氧基C1-C3烷基、氨基磺酰基或氨基磺酰基氧基C1-C3烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、羟基、巯基、羧基、-OR”、-(CO)R”、-SR”、-(SO2)R”、-O(CO)H、-O(CO)R”、-O-(SO2)R”、-(CO)OR”、-O(CO)OR”、-O(CO)(CO)OH、-O(CO)(CO)OR”、-O-(C1-C3烷基)-(CO)OH或-O-(C1-C3烷基)-(CO)OR”中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“氨基”、“氨基C1-C3烷基”、“氨基羰基C1-C3烷基”、“氨基羰基氧基C1-C3烷基”、“氨基硫代羰基氧基C1-C3烷基”、“氨基磺酰基”或“氨基磺酰基氧基C1-C3烷基”分别独立地是未取代的或被选自-R11、-OR11、-(CO)R11、-(CO)OR11、-(C1-C3烷基)-(CO)OR11、-(SO2)R11、-(SO2)OR11、-(C1-C3烷基)-(SO2)R11、-(CO)N(R12)2或-(SO2)N(R12)2中的一个或两个基团所取代的;R’分别独立地代表氢、卤素、C1-C6烷氧基、C1-C6烷氧基C1-C3烷基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、杂环基或杂环基C1-C3烷基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“杂环基”或“杂环基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;R”分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、芳基C2-C3烯基、杂环基、杂环基C1-C3烷基或杂环基C2-C3烯基,其中,所述“C1-C6烷基”、 “C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、三C1-C6烷基甲硅烷基、-OR13、-SR13、-O(CO)R13、-(CO)R13、-(CO)OR13或-O(CO)OR13中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“芳基C2-C3烯基”、“杂环基”、“杂环基C1-C3烷基”或“杂环基C2-C3烯基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环。
- 根据权利要求1-4任意一项所述的一种杂环取代的芳香类化合物,其特征在于,W3分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、杂环基、芳基、其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C8环烷基、三C1-C8烷基甲硅烷基、C3-C8环烯基、杂环基、芳基、 中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;W4、W5分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、杂环基、芳基、 其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C8环烷基、三C1-C8烷基甲硅烷基、C3-C8环烯基、杂环基、芳基、 中的至少一个基团所取代的,所述“C3-C8环烷基”、“C3-C8环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;或者NW4W5代表或者其是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的;X11分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、杂环基、杂环基C1-C8烷基、芳基或芳基C1-C8烷基,其中,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X12分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、杂环基、杂环基C1-C8烷基、芳基或芳基C1-C8烷基,其中,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“杂环基”、“杂环基C1-C8烷基”、“芳基”或“芳基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X13、X14分别独立地代表氢、卤素、氰基、C1-C8烷氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷基磺酰基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、芳基、芳基C1-C8烷基、杂环基或杂环基C1-C8烷基,或者基团CX13X14一起形成5~8元碳环或含氧、硫或氮的杂环,或者基团NX13X14一起形成 其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被 卤素取代的,所述“C3-C8环烷基”、“C3-C8环烷基C1-C8烷基”、“C3-C8环烯基”、“C3-C8环烯基C1-C8烷基”、“芳基”、“芳基C1-C8烷基”、“杂环基”或“杂环基C1-C8烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、卤代C1-C8烷基、卤代C2-C8烯基、卤代C2-C8炔基、卤代C3-C8环烷基、被C1-C8烷基取代的C3-C8环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C8烷基)-(CO)OR14中的至少一个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元碳环或含氧、硫或氮的杂环”是未取代的或被选自C1-C8烷基、C1-C8烷氧羰基或苄基中的至少一个基团所取代的,或者与芳基或杂环基形成稠环结构;所述是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的;优选地,W3分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、 中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;W4、W5分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、 其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、 中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6 环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;或者NW4W5代表或者其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;X11分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、杂环基、杂环基C1-C6烷基、芳基或芳基C1-C6烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X12分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、杂环基、杂环基C1-C6烷基、芳基或芳基C1-C6烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“杂环基”、“杂环基C1-C6烷基”、“芳基”或“芳基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X13、X14分别独立地代表氢、卤素、氰基、C1-C6烷氧基、C1-C6烷氧基C1-C6烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基磺酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、芳基、芳基C1-C6烷基、杂环基或杂环基C1-C6烷基,或者基团CX13X14一起形成5~8元饱和碳环、或者基团NX13X14一起形成其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C6烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C6烷基”、“芳基”、“芳基C1-C6烷基”、“杂环基”或“杂环基C1-C6烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6 环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C6烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元饱和碳环、”是未取代的或被选自C1-C6烷基、C1-C6烷氧羰基或苄基中的1、2或3个基团所取代的,或者与芳基或杂环基形成稠环结构,所述是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;更优选地,W3分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、 中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;W4、W5分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、杂环基、芳基、 其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被选自卤素、氰基、硝基、C3-C6环烷基、三C1-C6烷基甲硅烷基、C3-C6环烯基、杂环基、芳基、 中的1、2或3个基团所取代的,所述“C3-C6环烷基”、“C3-C6环烯基”、“杂环基”或“芳基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6 烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;或者NW4W5代表或者其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;X11分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、杂环基、杂环基C1-C3烷基、芳基或芳基C1-C3烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X12分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、杂环基、杂环基C1-C3烷基、芳基或芳基C1-C3烷基,其中,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“杂环基”、“杂环基C1-C3烷基”、“芳基”或“芳基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环;X13、X14分别独立地代表氢、卤素、氰基、C1-C6烷氧基、C1-C6烷氧基C1-C3烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基磺酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、芳基、芳基C1-C3烷基、杂环基或杂环基C1-C3烷基,或者基团CX13X14一起形成5~8元饱和碳环、或者基团NX13X14一起形成其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“C3-C6环烷基”、“C3-C6环烷基C1-C3烷基”、“C3-C6环烯基”、“C3-C6环烯基C1-C3烷基”、“芳基”、“芳基C1-C3烷基”、“杂环基”或“杂环基C1-C3烷基”分别独立地是未取代的或被选自氧代、卤素、氰基、硝基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、卤代C1-C6烷基、卤代C2-C6烯基、卤代C2-C6炔基、卤代C3-C6环烷基、被 C1-C6烷基取代的C3-C6环烷基、-OR14、-SR14、-(CO)OR14、-(SO2)R14、-N(R14)2或-O-(C1-C3烷基)-(CO)OR14中的1、2或3个基团所取代的,或者环上相邻两个碳原子与未取代的或被卤素所取代的-OCH2CH2-或-OCH2O-形成稠环,所述“5~8元饱和碳环、”是未取代的或被选自C1-C6烷基、C1-C6烷氧羰基或苄基中的1、2或3个基团所取代的,或者与苯基或噻吩基形成稠环结构;所述是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的。
- 根据权利要求1-5任意一项所述的一种杂环取代的芳香类化合物,其特征在于,R11分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C3-C8环烯基C1-C8烷基、苯基或苄基,其中,所述“C1-C8烷基”、“C2-C8烯基”或“C2-C8炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的;R12分别独立地代表氢、C1-C8烷基、C2-C8烯基、C2-C8炔基、C1-C8烷氧基、C1-C8烷基磺酰基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基或C3-C8环烯基C1-C8烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表 其是未取代或被选自氧代、C1-C8烷基或C1-C8烷氧羰基中的至少一个基团所取代的;R13分别独立地代表C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、苯基或被选自以下至少一个基团所取代的苯基:卤素,氰基,硝基,C1-C8烷基,卤代C1-C8烷基,C1-C8烷氧基,卤代C1-C8烷氧基,C1-C8烷氧基羰基,C1-C8烷硫基,C1-C8烷基磺酰基或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的苯氧基;R14分别独立地代表氢,C1-C8烷基,卤代C1-C8烷基,苯基或被选自卤素、氰基、硝基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基、C1-C8烷氧基或卤代C1-C8烷氧基中的至少一个基团所取代的苯基;优选地,R11分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C3-C6环烯基C1-C6烷基、苯基或苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6 烷氧基中的1、2或3个基团所取代的;R12分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷基磺酰基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基或C3-C6环烯基C1-C6烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表 其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;R13分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、苯基或被选自以下1、2或3个基团所取代的苯基:卤素,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基羰基,C1-C6烷硫基,C1-C6烷基磺酰基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯氧基;R14分别独立地代表氢,C1-C6烷基,卤代C1-C6烷基,苯基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯基;更优选地,R11分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基、C3-C6环烯基C1-C3烷基、苯基、苄基,其中,所述“C1-C6烷基”、“C2-C6烯基”或“C2-C6炔基”分别独立地是未取代的或被卤素取代的,所述“苯基”或“苄基”分别独立地是未取代的或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的;R12分别独立地代表氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷基磺酰基、C3-C6环烷基、C3-C6环烷基C1-C3烷基、C3-C6环烯基或C3-C6环烯基C1-C3烷基,或者-(CO)N(R12)2或-(SO2)N(R12)2中的基团N(R12)2分别独立地代表 其是未取代或被选自氧代、C1-C6烷基或C1-C6烷氧羰基中的1、2或3个基团所取代的;R13分别独立地代表C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、苯基或被选自以下1、2或3个基团所取代的苯基:卤素,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷氧基羰基,C1-C6烷硫基,C1-C6烷基磺酰基或被选自卤素、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯氧基;R14分别独立地代表氢,C1-C6烷基,卤代C1-C6烷基,苯基或被选自卤素、氰基、硝 基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷氧基或卤代C1-C6烷氧基中的1、2或3个基团所取代的苯基;进一步优选地,所述化合物选自表1中任意一个。
- 一种如权利要求1-6任意一项所述的杂环取代的芳香类化合物的制备方法,其特征在于,包括以下步骤:将通式II所示的化合物与通式III所示的化合物进行反应制得如通式I所示的化合物,其化学反应方程式如下:
其中,Hal代表卤素,取代基X1、X2、R1、R2、R3、R4、M1、M2、Q、Y和Z的定义如权利要求1-6任意一项所示;优选地,所述反应在碱和溶剂的存在下进行;更优选地,所述碱选自含氮碱中的至少一种;所述溶剂选自芳香烃、THF、DMF、DMA、甲醇、乙醇、乙腈、二氯乙烷、DMSO、Dioxane、二氯甲烷、甲苯或乙酸乙酯中的至少一种。 - 一种除草剂组合物,其特征在于,包括除草有效量的权利要求1-6任意一项所述的杂环取代的芳香类化合物中的至少一种,优选地,还包括制剂助剂。
- 一种控制杂草的方法,其特征在于,包括将除草有效量的权利要求1-6任意一项所述的杂环取代的芳香类化合物中的至少一种或权利要求8所述的除草剂组合物使用在植物上或者杂草区域。
- 如权利要求1-6任意一项所述的杂环取代的芳香类化合物中的至少一种或权利要求8所述的除草剂组合物在控制杂草上的用途,优选地,将所述的杂环取代的芳香类化合物用于防除有用作物中的杂草,所述有用作物为转基因作物或者基因组编辑技术处理过的作物。
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