WO2020133090A1 - 吡啶氧基硫酯衍生物及其制备方法、除草组合物和应用 - Google Patents
吡啶氧基硫酯衍生物及其制备方法、除草组合物和应用 Download PDFInfo
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- WO2020133090A1 WO2020133090A1 PCT/CN2018/124458 CN2018124458W WO2020133090A1 WO 2020133090 A1 WO2020133090 A1 WO 2020133090A1 CN 2018124458 W CN2018124458 W CN 2018124458W WO 2020133090 A1 WO2020133090 A1 WO 2020133090A1
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- alkyl
- halogen
- substituted
- alkoxy
- cycloalkyl
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- 0 CCCN(*)CC Chemical compound CCCN(*)CC 0.000 description 4
- UQFQONCQIQEYPJ-UHFFFAOYSA-N C[n]1nccc1 Chemical compound C[n]1nccc1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 2
- MYDVTZNUNWJXTJ-UHFFFAOYSA-N CC(C(SCCON=C(C)C)=O)[BrH]C Chemical compound CC(C(SCCON=C(C)C)=O)[BrH]C MYDVTZNUNWJXTJ-UHFFFAOYSA-N 0.000 description 1
- MHULSFRXFKVOBK-UHFFFAOYSA-N CC(C)=NOCCS Chemical compound CC(C)=NOCCS MHULSFRXFKVOBK-UHFFFAOYSA-N 0.000 description 1
- WWKLDHMLHHWLKP-UHFFFAOYSA-N CCSC(C(C)Br)=O Chemical compound CCSC(C(C)Br)=O WWKLDHMLHHWLKP-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N CN1CCOCC1 Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- YCQHTIDVLROXSL-UHFFFAOYSA-N IN1CCOCC1 Chemical compound IN1CCOCC1 YCQHTIDVLROXSL-UHFFFAOYSA-N 0.000 description 1
- IYWQCCHIVFXZML-UHFFFAOYSA-N I[n]1nccc1 Chemical compound I[n]1nccc1 IYWQCCHIVFXZML-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the invention belongs to the technical field of pesticides, and specifically relates to a pyridyloxythioester derivative, a preparation method thereof, a herbicidal composition and applications.
- the present invention provides a pyridyloxythioester derivative, its preparation method, herbicidal composition and application.
- the compound has excellent herbicidal activity and higher crop safety, especially for rice and other key crops. Good selectivity.
- a and B independently represent halogen, with or without halogen alkyl or cycloalkyl
- C represents hydrogen, halogen, alkyl, haloalkyl
- Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl, alkyl or alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio without or containing halogen , Alkylcarbonyl, alkoxycarbonyl, alkylaminoalkyl or alkoxyalkyl, unsubstituted or substituted aryl, heteroaryl, arylalkyl, heteroarylalkyl;
- M represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, -alkyl-R, free or containing halogen And unsubstituted or substituted heterocyclic, aryl, heteroaryl;
- R stands for Cyano, nitro
- R 3 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, and unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl Group, heteroarylalkyl;
- R 4 , R 5 , and R 6 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl, and unsubstituted or substituted heterocyclic group, aryl, Heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl;
- R 11 independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, unsubstituted or substituted aryl, Heteroaryl
- R 12 represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy;
- R 13 represents H, alkyl, haloalkyl, phenyl, benzyl or CHR 31 C(O)OR 32 ;
- R 31 represents H, alkyl or alkoxy;
- R 32 represents H, alkyl or benzyl;
- R 14 represents alkyl, haloalkyl
- R 15 represents H, alkyl, formyl, alkyl acyl, haloalkyl acyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl;
- R 16 represents H, alkyl;
- R 17 represents H, alkyl, unsubstituted or substituted with 1-3 groups in halogen, alkyl, alkoxy;
- R 21 and R 24 independently represent H or alkyl
- R 22 and R 23 independently represent H or alkyl; or NR 22 R 23 represents a 5- or 6-membered saturated or unsaturated ring that does not contain or contains an oxygen atom, sulfur atom or other nitrogen atom;
- R 25 represents an alkyl group.
- a and B independently represent halogen, C1-C8 alkyl or C3-C8 cycloalkyl with or without halogen;
- C represents hydrogen, halogen, C1-C8 alkyl, halogenated C1-C8 alkyl;
- Q represents halogen, cyano, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, amino, nitro, formyl, C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2- C8 alkynyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylamino C1-C8 alkyl Group or C1-C8 alkoxy C1-C8 alkyl, unsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl;
- M stands for C1-C18 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, or -(C1-C8 Alkyl)-R, And unsubstituted or substituted heterocyclic, aryl, heteroaryl;
- R stands for Cyano, nitro
- R 3 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, and unsubstituted or substituted heterocycle Aryl, aryl, heteroaryl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl;
- R 4 , R 5 , R 6 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl , C1-C8 alkoxycarbonyl and unsubstituted or substituted heterocyclic C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl;
- R 11 independently represents halogen, hydroxy, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylthio, halogenated C1-C8 alkylthio, amino, C1-C8 alkylamino , Di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl, unsubstituted or substituted by halogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, nitro 1- 3 groups substituted phenyl, naphthyl,
- R 12 represents H, C1-C18 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, phenyl, phenoxy or benzyloxy;
- R 13 represents H, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl, benzyl or CHR 31 C(O)OR 32 ;
- R 31 represents H, C1-C8 alkyl or C1-C8 alkoxy Radical;
- R 32 represents H, C1-C8 alkyl or benzyl;
- R 14 represents C1-C8 alkyl, halogenated C1-C8 alkyl
- R 15 represents H, C1-C8 alkyl, formyl, C1-C8 alkyl acyl, halogenated C1-C8 alkyl acyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl;
- R 16 represents H, C1-C8 alkyl;
- R 17 represents H, C1-C8 alkyl, unsubstituted or substituted by 1-3 groups in halogen, C1-C8 alkyl, C1-C8 alkoxy;
- R 21 and R 24 independently represent H or C1-C8 alkyl
- R 22 and R 23 independently represent H or C1-C8 alkyl; or NR 22 R 23 represents
- R 25 represents C1-C8 alkyl
- heterocyclic group means a group having 0, 1, or 2 oxo groups
- aryl refers to phenyl and naphthyl; the “heteroaryl” refers to an aromatic ring containing 3 to 6 ring atoms and also fused through a benzo ring Group, 1 to 4 heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example, Wherein it is substituted by at least one group selected from halogen, alkyl, alkoxy, unsubstituted or substituted by halogen, nitro, cyano, cyanothio, hydroxy, carboxy, mercapto, formyl, etc.
- R'independently represents hydrogen, nitro, hydroxy, amino, alkyl with or without halogen, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyl Oxygen, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylthiocarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkane Group, alkylacyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, dialkylphosphono;
- R" independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl, respectively.
- a and B independently represent halogen, C1-C6 alkyl or C3-C6 cycloalkyl with or without halogen;
- C represents hydrogen, halogen, C1-C6 alkyl, halogenated C1-C6 alkyl;
- Q represents halogen, cyano, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, amino, nitro, formyl, C1-C6 alkyl without or containing halogen, C2-C6 alkenyl, C2- C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylamino C1-C6 alkyl Group or C1-C6 alkoxy C1-C6 alkyl, unsubstituted or substituted aryl, heteroaryl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl;
- M represents C1-C12 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, or -(C1-C6 Alkyl)-R, And unsubstituted or substituted heterocyclic, aryl, heteroaryl;
- R stands for Cyano, nitro
- R 3 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, and unsubstituted or substituted heterocycle Group, aryl, heteroaryl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl;
- R 4 , R 5 , R 6 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl , C1-C6 alkoxycarbonyl and unsubstituted or substituted heterocyclic C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl;
- R 11 independently represents halogen, hydroxy, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, amino, C1-C6 alkylamino , Di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl, unsubstituted or substituted by halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, nitro 1- 3 groups substituted phenyl, naphthyl,
- R 12 represents H, C1-C14 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy or benzyloxy;
- R 13 represents H, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, benzyl or CHR 31 C(O)OR 32 ;
- R 31 represents H, C1-C6 alkyl or C1-C6 alkoxy Radical;
- R 32 represents H, C1-C6 alkyl or benzyl;
- R 14 represents C1-C6 alkyl, halogenated C1-C6 alkyl
- R 15 represents H, C1-C6 alkyl, formyl, C1-C6 alkyl acyl, halogenated C1-C6 alkyl acyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl;
- R 16 represents H, C1-C6 alkyl;
- R 17 represents H, C1-C6 alkyl, unsubstituted or substituted by 1-3 groups in halogen, C1-C6 alkyl, C1-C6 alkoxy;
- R 21 and R 24 independently represent H or C1-C6 alkyl
- R 22 and R 23 independently represent H or C1-C6 alkyl; or NR 22 R 23 represents
- R 25 represents C1-C6 alkyl
- heterocyclic group means a group having 0, 1, or 2 oxo groups
- aryl refers to phenyl and naphthyl; the “heteroaryl” refers to Among them, it is selected from halogen, nitro, cyano, cyanothio, hydroxyl, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy at least Phenyl, benzyl, benzyloxy, phenoxy substituted with one group, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl with or without halogen , C3-C6 cycloalkyl C1-C6 alkyl, OR", SR", -(C1-C6)alkyl-OR", -(C1-C6)alkyl-SR", COR",
- R'independently represents hydrogen, nitro, hydroxy, amino, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, with or without fluorine, chlorine, or bromine C3-C6 cycloalkenyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy , C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C6
- R" independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl.
- a and B independently represent halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, and C3-C6 cycloalkyl;
- C represents hydrogen, halogen, C1-C6 alkyl, halogenated C1-C6 alkyl;
- Q represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, cyano, amino, nitro, formyl, C1- C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C2 alkyl, cyano C1-C2 alkyl, C1-C6 alkyl Amino C1-C2 alkyl, benzyl, naphthyl, furanyl, thienyl, thiazolyl, pyridyl, pyrimidinyl, and unsubstituted or substituted by C1-C6 alkyl Unsubstituted or substituted by at least one group of C1-C6 alkyl, halogenated C1
- M represents C1-C12 alkyl (preferably C1-C8 alkyl, more preferably C1-C6 alkyl), halogenated C1-C8 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 Alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, cyano C1-C6 alkyl, nitro C1-C6 alkyl, C1-C6 Alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C2-C6 alkenyloxycarbonyl C1-C6 alkyl, -(C1-C6 alkyl)-R, Tetrahydrofuranyl, pyridyl, naphthyl, furyl, thienyl, And un
- R 3 independently represents C1-C6 alkyl
- R 4 , R 5 , and R 6 independently represent hydrogen, C1-C6 alkyl, and C1-C6 alkoxycarbonyl;
- R’ represents C1-C6 alkyl, halogenated C1-C6 alkyl
- X represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino, phenylcarbonylamino, benzylamino, unsubstituted or halogenated C1-C6 alkyl-substituted furylmethyleneamino.
- a and B independently represent fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, trifluoromethyl, and cyclopropyl;
- C represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl
- Q represents methyl, ethyl, propyl, isopropyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, cyano, amino, nitro, formyl, methoxy, methylthio, Methoxycarbonyl, monochloromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, hydroxymethyl, Benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl, pyrimidinyl, and unsubstituted or substituted with methyl Phenyl that is unsubstituted or substituted with at least one group among methyl, trifluoromethyl, chlorine and methoxy;
- R’ represents methyl, ethyl, difluoromethyl
- M represents methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl Alkyl, dodecyl, trifluoromethyl, pentafluoroethyl, 3-chlorobutyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 4,4,4-trifluorobutyl, 2,2,3,3,3-pentafluoropropyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, allyl, 2-propynyl, methoxy, ethoxycarbonyl, methyls
- alkyl groups having more than two carbon atoms may be straight-chain or Branched.
- the alkyl group may be -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )-, -C(CH 3 ) 2 -, etc.
- the alkyl group is , For example, methyl; ethyl; n-propyl or isopropyl; n-butyl, isobutyl, tert-butyl or 2-butyl; pentyl; hexyl, such as n-hexyl, isohexyl and 1,3- Dimethylbutyl.
- Halogen is fluorine, chlorine, bromine or iodine.
- a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups which are the same or different groups 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 compounds of general formula I may exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may appear.
- the stereoisomers can be obtained from the mixture obtained in the preparation by a conventional separation method, for example, by a chromatographic separation method.
- the stereoisomers can also be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries.
- the invention also relates to all stereoisomers and mixtures thereof which are included in the general formula I but not specifically defined.
- the preparation method of the pyridyloxythio ester derivative includes the following steps:
- W represents alkali metal, preferably K, Na;
- Hal represents halogen, preferably Br, Cl;
- the reaction is carried out in the presence of a catalyst and a solvent, preferably, the catalyst is TBAB, and the solvent is DCM, DCE, One or more combinations of ACN, THF, DMF.
- the halide is preferably a chloride or a bromide
- the reaction is carried out in the presence of a base and a solvent
- the base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and cesium carbonate One or more than two
- the solvent is selected from one of THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, methylene chloride, and chloroform One or more combinations
- a catalyst may also be added during the reaction, preferably DMAP.
- a herbicidal composition comprising (i) at least one of pyridyloxythioester derivatives represented by formula I; preferably, further comprising (ii) one or more additional herbicides and/or safe Agents; more preferably, (iii) agrochemically acceptable formulation aids.
- a method for controlling weeds comprising using a herbicidally effective amount of at least one of the pyridyloxythioester derivatives or the herbicide composition on plants or weed areas, preferably
- the plants are rice (such as japonica rice, indica rice), the weeds are grasses (such as barnyard grass, crabgrass, Qianjin, and foxtail), broad-leaved grasses (such as velvetleaf, ragweed), and sedge weeds (Such as crushed miza grass).
- the useful crops are transgenic crops or crops treated by genome editing technology, more preferably, the crops are rice (such as japonica, indica), and the weeds are grasses (such as barnyard grass, horse Tang, Qianjinjin, Setaria), broad-leaved grasses (such as velvetleaf, ragweed) and sedge weeds (such as crushed sedge).
- the crops are rice (such as japonica, indica)
- the weeds are grasses (such as barnyard grass, horse Tang, Qianjinjin, Setaria), broad-leaved grasses (such as velvetleaf, ragweed) and sedge weeds (such as crushed sedge).
- the compounds of formula I according to the invention have outstanding herbicidal activity.
- the active substance of the present invention is also effective for perennial weeds, which grow from rhizomes, rhizomes, or other perennial organs, and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before germination or after germination. Particular mention is made of representative examples of monocotyledonous and dicotyledonous weed colonies that can be controlled by the compounds of the present invention, and there is no limitation to certain species.
- weed species in which the active substance works effectively include monocotyledons: annual oats, rye, grasses, hordeum, ferraris, barnyardgrass, crabgrass, foxtail and sedge, and perennial ice Grasses, bermudagrass, chrysanthemum and sorghum, and perennial sedges.
- dicotyledonous weed species the effects of which can be extended to species such as the annual Swigella, Viola, Pompona, Wild Sesame, Stellaria, Amaranthus, Sphaeropsis, Ipomoea, Hirsch Genus, Matricaria and Abutilon, and perennial weeds Convolvulus, Thistle, Rumex and Artemisia.
- the active substance of the present invention can effectively control harmful plants, such as barnyardgrass, genus Astragalus, Alisma, water chestnut, cane grass and sedge, under such conditions as rice seeding.
- weed seedlings can be completely prevented before the weeds grow, or the weeds can stop growing when they grow cotyledons, and finally die completely after three to four weeks.
- the compounds of the present invention are particularly active against the following plants: Apila, Ono sesame, Polygonum sibiricum, Stellaria, Ivy leaf Pomna, Arab Pomna, Pansy and Amaranthus, Potentilla and Kochia .
- the compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, it is not harmful to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybean , Or the damage is negligible. Especially compatible with cereal crops, such as wheat, barley and corn, especially wheat. Therefore, the compound of the present invention is very suitable for selectively controlling useless plants in agricultural or ornamental plants.
- Transgenic plants Due to their herbicidal properties, these active substances can be used to control harmful plants in the cultivation of genetically engineered plants that are known or will appear.
- Transgenic plants generally have superior traits, such as resistance to specific insecticides, especially specific herbicides, resistance to plant diseases or pathogenic microorganisms of plant diseases, such as specific insect or fungal, bacterial or viral microorganisms.
- Other special characteristics are related to the following conditions of the product, for example, quantity, quality, storage stability, components and special ingredients. As such, it is known that the obtained transgenic plant products have increased starch content or improved starch quality or different fatty acid compositions.
- the compounds of the formula I of the present invention or salts thereof are preferably used for economically important transgenic crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or for sugar beet, Cultivation of cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants.
- the compounds of formula I are preferably used as herbicides for the cultivation of useful plants, which plants are resistant or have a resistance to the toxic effects of the herbicides through genetic engineering.
- 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-suppression effect, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcription products 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 DNA molecules that contain only a portion of the coding sequence, which must be long enough to achieve antisense in the cell Effect. It is also possible to use sequences that have a high degree of homology to the gene product coding sequence but are not completely identical.
- the synthesized protein When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired plant cell compartment. However, in order to locate in a specific chamber, it is possible, for example, to connect the coding region and the DNA sequence to ensure the localization at a specific position. These sequences are known to those skilled in the art (see, for example, 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 recombined into whole plants using known techniques.
- the control can be improved or expanded
- the range of weeds, improved application rates during application preferably a good combination of the resistance of transgenic crops and the performance of herbicides, and the effects of growth and yield of transgenic crop plants. Therefore, the present invention also provides the use of the compound as a herbicide for controlling harmful plants in transgenic crop plants.
- the compounds of the present invention can significantly regulate the growth of crop plants. By regulating participation in plant metabolism, these compounds are used to directionally control plant components and promote harvesting, such as drying and dwarfing plant growth. And they are also suitable for regulating and inhibiting undesired plant growth without destroying the growth of crops. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops, because this can reduce or completely prevent lodging.
- the compound of the present invention can be applied using general preparations, and wettable powders, concentrated emulsions, sprayable solutions, powders or granules can be used.
- the present invention also provides herbicide compositions comprising compounds of formula I.
- the compound of formula I can be formulated in a variety of ways according to the usual biological and/or chemical physical parameters.
- wettable powders WP
- water-soluble powders SP
- water-soluble concentrates such as oil-in-water dispersion and water-in-oil dispersion emulsion (EW)
- Sprayable solution suspension concentrate (SC)
- dispersible oil suspension OD
- suspension with oil or water as diluent solution of miscible oil
- powder DP
- capsule suspension CS
- seeddressing composition particles for spreading and soil application, spraying particles, coating particles and absorbing particles
- water-dispersible particles WG
- water-soluble particles SG
- ULV super Low volume
- Necessary formulation aids such as inert substances, surfactants, solvents and other additives are also known and described in the following documents, such as Watkins'"Handbook of Powder Diluent Insecticides and Carriers", Second Edition, Darland book Caldwell NJ; Hv01phen "Introduction to Clay Colloid Chemistry", Second Edition, 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 polyethoxyalkylphenol, poly Ethoxy fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2,2'-dinaphthyl methane -6,6'-Sodium disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoyl methyl taurine.
- the active substances of the herbicides are finely ground, for example, using commonly used instruments, such as hammer mills, fan mills and jet mills, and the adjuvants are mixed simultaneously or sequentially.
- Solvents such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and then add one One or more ionic and/or nonionic surfactants (emulsifiers).
- emulsifiers examples include calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbitan such as polyoxyethylene sorbitan fatty acid ester Polysaccharide ester.
- calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or poly
- the active substance and finely divided solid substance are ground to obtain a powder, such as talc, natural clay such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- a powder such as talc, natural clay such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- the suspension based on water or oil can be prepared by a method such as wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of the other formulation type described above.
- an organic solvent containing water can be used, a stirrer, a colloid grinder, and/or a static mixer, and if necessary, a surfactant of another formulation type as described above is added.
- granules by the following method, spray the active substance onto the adsorbate, granulate with inert material, or concentrate the active substance to the surface of the carrier such as sand, kaolinite, granulate the inert material through a binder, stick Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil.
- the method of preparing fertilizer granules can be used to pelletize suitable active substances, and fertilizers can be mixed if necessary.
- Aqueous granules are prepared using conventional methods, such as spray-drying, fluidized bed granulation, milling disk granulation, mixing using a high-speed mixer, and extruding without solid inert materials.
- Agrochemical formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% of active substance formula I.
- the concentration of the active substance in the wettable powder is, for example, from about 10 to 99% by weight, and the usual formulation components constitute the remaining amount to 100% by weight.
- the concentration of the active substance in the concentrated emulsion can be about 1 to 90% by weight, preferably 5 to 80%.
- Powder formulations contain 1 to 30% by weight of active substance, usually preferably 5 to 20% by weight of active substance, whereas sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% of active substance .
- Regarding the content of active substances in water-suspended granules it mainly depends on whether the active substances are liquid or solid, and the auxiliary agents, fillers, etc. used in granulation.
- the content of active substance in the water-suspended 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 a tackifier, wetting agent, dispersant, emulsifier, penetrant, preservative, antifreeze, solvent, filler, carrier, colorant, defoamer, evaporation inhibitor and PH and viscosity modifiers are commonly used in all cases.
- the mixing method may be For pre-mixing or filling and mixing.
- suitable active substances that can be mixed with the active substance of the present invention are, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the documents cited here Known substances.
- the herbicide active substances mentioned below can be mixed with the mixture of formula I, (note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, where appropriate, code): acetochlor Amine, butachlor, alachlor, propolachlor, metolachlor, sinoprofen, alachlor, alachlor, toxachlor, oxachlor, naproxen, R-levonal Alachlor, Dipropanil, fenclofen, difenochlor, fenfluramide, alafenamide, flufenacetamide, bromobutanil, dimethyl thiazopyr, highly effective dimethyl Tetrachlor, ethoxyfen, chlorfenapyr, tetromethoxam, metazachlor, clomazone, high-efficiency methyl strawgrass, high-efficiency propylpropoxylate, dimethochlor, dimethoprim , Butachlor, cyprochlor,
- the commercially available formulations are diluted in the usual manner, for example, in the case of wettable powders, concentrated emulsions, suspensions and particles suspended in water, diluted with water. Powders, granules for soil application or solutions for spreading and spraying generally do not need to be further diluted with inert substances before use.
- the external conditions change, the required amount of the compound of formula I is also different.
- the external conditions are, for example, temperature, humidity, the nature of the herbicide used, and so on. It can have a large range of variation, for example between 0.001 and 1.0 kg/ha, or more active substances, but preferably between 0.005 and 750 g/ha, especially between 0.005 and 500 g/ha.
- step (2) Place compound a (400 mg, 2.13 mmol), compound 66-2 (1.2 g, crude product) obtained in step (1), catalytic amount of TBAB (10 mg), DMF (10 mL) in a 50 mL round bottom flask , Heated to 85 °C for 12 hours. After the liquid quality detection, the raw materials were reacted, the reaction was cooled to room temperature, water (100 mL) and methyl tert-butyl ether (50 mL x 2) were extracted, the organic phase was dried and concentrated, and compound 66 (300 mg, yield 56) was obtained after column separation %), compound 66 is a white solid.
- reaction solution was concentrated to remove methanol, extracted with water (100 mL) and ethyl acetate (100 mL x 2), and the organic phase was dried and concentrated to obtain compound 97-3 (500 mg, crude product), which was directly used in the next reaction without purification.
- compound 4 was prepared, and then compound 4 (200 mg, 0.67 mmol), potassium carbonate (185 mg, 1.34 mmol), compound 130-1 (161 mg, 1.00 mmol), catalytic amount of DMAP (10 mg), Acetonitrile (20 mL) was placed in a 50 mL round bottom flask and heated to 80°C for 12 hours. After the liquid quality detection of the raw materials was completed, the reaction was cooled to room temperature, concentrated, and separated by column chromatography to obtain compound 130 (150 mg, yield 59%). Compound 130 was a colorless oil.
- the standard of activity level of harmful plant destruction (ie growth control rate) is as follows:
- Level 5 The growth control rate is above 85%;
- Level 4 The growth control rate is greater than or equal to 60% and less than 85%;
- Level 3 Growth control rate is greater than or equal to 40% and less than 60%;
- Level 2 The growth control rate is greater than or equal to 20% and less than 40%;
- Level 1 The growth control rate is greater than or equal to 5% and less than 20%;
- Level 0 The growth control rate is less than 5%.
- the above growth control rate is the fresh weight control rate.
- Post-emergence test experiment Place monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet, sorghum) in a plastic pot filled with soil, and then cover 0.5-2 Centimeters of soil to grow in a good greenhouse environment, treat the test plants at the 2-3 leaf stage after sowing for 2 weeks, dissolve the tested compounds of the invention with acetone, then add Tween 80 at 1.5 liters/ha
- the emulsifiable concentrate of methyl oleate is used as a synergist, diluted with a certain amount of water to a solution of a certain concentration, and sprayed onto the plants with a spray tower. After the application, the plants were cultivated in the greenhouse for 3 weeks. After 3 weeks, the experimental effects of weeds are listed in Table 3-4.
- the application dose is 600 g/ha for the active ingredient and the water content is 450 kg/ha.
- Barnyard grass and crushed rice sedges were collected from Ningxia, China, and developed resistance to ALS herbicides.
- Control compound A is a known compound, which has poor safety to rice and low selection index, and is difficult to use commercially.
- the compound of the present invention has a high selection index for rice, good safety, and good commercial value. Moreover, it has an excellent effect on ALS barnyard grass and crushed rice sedge in rice fields, and can solve resistant weeds.
- the compound of the present invention to be tested was dissolved in acetone, then Tween 80 was added, diluted with a certain amount of water to a solution of a certain concentration, and sprayed immediately after sowing.
- the compounds of the present invention generally have better weed control effects, especially for the major grass weeds such as barnyardgrass, horsetail, foxtail, and velvetleaf widely occurring in corn fields, rice fields, and wheat fields.
- Broadleaf, needleweed and other major broad-leaved weeds have good results and have good commercial value.
- the broadleaf weeds that are resistant to ALS inhibitors such as Chestnut, Artemisia sibiricum, Shepherd's purse, Maijiagong, Swamp, and Stellaria, have extremely high activity.
- the water-dilutable solution of the wettable powder or suspending agent prepared by the compound of the present invention according to the usual preparation method is evenly distributed with a pipette. Drop treatment to achieve the specified amount of active ingredients.
- the compound of the present invention was treated in the same manner as described above.
- the seeds of Agaricus platyphylla are all collected from Heilongjiang, China. After testing, they are resistant to the conventional doses of pyrazosulfuron-methyl and penoxsulam.
- the compounds of the present invention have excellent activity against weeds that face serious challenges in the mechanism of anti-ALS inhibition, and can solve the increasingly serious problem of resistance.
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Abstract
Description
化合物序号 | 猪殃殃 | 千金子 | 马唐 | 狗尾草 | 苘麻 | 鸭舌草 |
1 | 5 | 5 | 5 | 5 | 5 | 5 |
2 | 5 | 5 | 5 | 5 | 5 | 5 |
3 | 5 | 5 | 5 | 5 | 5 | 5 |
4 | 5 | 5 | 5 | 5 | 5 | 5 |
5 | 5 | 5 | 5 | 5 | 5 | 5 |
6 | 5 | 5 | 5 | 5 | 5 | 5 |
7 | 5 | 5 | 5 | 5 | 5 | 5 |
8 | 5 | 5 | 5 | 5 | 5 | 5 |
9 | 5 | 5 | 5 | 5 | 5 | 5 |
10 | 5 | 5 | 5 | 5 | 5 | 5 |
11 | 5 | 5 | 5 | 5 | 5 | 5 |
12 | 5 | 5 | 5 | 5 | 5 | 5 |
13 | 5 | 5 | 5 | 5 | 5 | 5 |
14 | 5 | 5 | 5 | 5 | 5 | 5 |
15 | 5 | 5 | 5 | 5 | 5 | 5 |
16 | 5 | 5 | 5 | 5 | 5 | 5 |
17 | 5 | 5 | 5 | 5 | 5 | 5 |
18 | 5 | 5 | 5 | 5 | 5 | 5 |
19 | 5 | 5 | 5 | 5 | 5 | 5 |
20 | 5 | 5 | 5 | 5 | 5 | 5 |
21 | 5 | 5 | 5 | 5 | 5 | 5 |
22 | 5 | 5 | 5 | 5 | 5 | 5 |
23 | 5 | 5 | 5 | |||
24 | 5 | 5 | 5 | |||
25 | 5 | 5 | 5 | |||
26 | 5 | 5 | 5 | |||
27 | 5 | 5 | 5 | |||
28 | 5 | 5 | 5 | |||
29 | 5 | 5 | 5 | |||
30 | 5 | 5 | 5 | |||
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32 | 5 | 5 | 5 | |||
33 | 5 | 5 | 5 | |||
34 | 5 | 5 | 5 | |||
35 | 5 | 5 | 5 | |||
36 | 5 | 5 | 5 | |||
37 | 5 | 5 | 5 | |||
38 | 5 | 5 | 5 | |||
39 | 5 | 5 | 5 | |||
40 | 5 | 5 | 5 | |||
41 | 5 | 5 | 5 | |||
42 | 5 | 5 | 5 | |||
43 | 5 | 5 | 5 | |||
44 | 5 | 5 | 5 | |||
45 | 5 | 5 | 5 | |||
46 | 5 | 5 | 5 | |||
47 | 5 | 5 | 5 | |||
48 | 5 | 5 | 5 | |||
49 | 5 | 5 | 5 | |||
50 | 5 | 5 | 5 | |||
51 | 5 | 5 | 5 |
52 | 5 | 5 | 5 | |||
53 | 5 | 5 | 5 | |||
54 | 5 | 5 | 5 | |||
55 | 5 | 5 | 5 | |||
56 | 5 | 5 | 5 | |||
57 | 5 | 5 | 5 | |||
58 | 5 | 5 | 5 | |||
59 | 5 | 5 | 5 | |||
60 | 5 | 5 | 5 | |||
61 | 5 | 5 | 5 | |||
62 | 5 | 5 | 5 | |||
63 | 5 | 5 | 5 | |||
64 | 5 | 5 | 5 | |||
65 | 5 | 5 | 5 | |||
66 | 5 | 5 | 5 | 5 | 5 | 5 |
67 | 5 | 5 | 5 | 5 | 5 | 5 |
68 | 5 | 5 | 5 | 5 | 5 | 5 |
69 | 5 | 5 | 5 | 5 | 5 | 5 |
70 | 5 | 5 | 5 | 5 | 5 | 5 |
71 | 5 | 5 | 5 | 5 | 5 | 5 |
72 | 5 | 5 | 5 | 5 | 5 | 5 |
73 | 5 | 5 | 5 | 5 | 5 | 5 |
74 | 5 | 5 | 5 | 5 | 5 | 5 |
75 | 5 | 5 | 5 | 5 | 5 | 5 |
76 | 5 | 5 | 5 | 5 | 5 | 5 |
77 | 5 | 5 | 5 | 5 | 5 | 5 |
78 | 5 | 5 | 5 | 5 | 5 | 5 |
79 | 5 | 5 | 5 | 5 | 5 | 5 |
80 | 5 | 5 | 5 | 5 | 5 | 5 |
81 | 5 | 5 | 5 | 5 | 5 | 5 |
82 | 5 | 5 | 5 | 5 | 5 | 5 |
83 | 5 | 5 | 5 | 5 | 5 | 5 |
84 | 5 | 5 | 5 | 5 | 5 | 5 |
85 | 5 | 5 | 5 | 5 | 5 | 5 |
86 | 5 | 5 | 5 | 5 | 5 | 5 |
87 | 5 | 5 | 5 | 5 | 5 | 5 |
88 | 5 | 5 | 5 | 5 | 5 | 5 |
89 | 5 | 5 | 5 | 5 | 5 | 5 |
90 | 5 | 5 | 5 | 5 | 5 | 5 |
91 | 5 | 5 | 5 | 5 | 5 | 5 |
92 | 5 | 5 | 5 | 5 | 5 | 5 |
93 | 5 | 5 | 5 | 5 | 5 | 5 |
94 | 5 | 5 | 5 | 5 | 5 | 5 |
95 | 5 | 5 | 5 | 5 | 5 | 5 |
96 | 5 | 5 | 5 | 5 | 5 | 5 |
97 | 5 | 5 | 5 | 5 | 5 | 5 |
98 | 5 | 5 | 5 | 5 | 5 | 5 |
99 | 5 | 5 | 5 | 5 | 5 | 5 |
100 | 5 | 5 | 5 | 5 | 5 | 5 |
101 | 5 | 5 | 5 | 5 | 5 | 5 |
102 | 5 | 5 | 5 | 5 | 5 | 5 |
103 | 5 | 5 | 5 | 5 | 5 | 5 |
104 | 5 | 5 | 5 | 5 | 5 | 5 |
105 | 5 | 5 | 5 | 5 | 5 | 5 |
106 | 5 | 5 | 5 | 5 | 5 | 5 |
107 | 5 | 5 | 5 | 5 | 5 | 5 |
108 | 5 | 5 | 5 | 5 | 5 | 5 |
109 | 5 | 5 | 5 | 5 | 5 | 5 |
110 | 5 | 5 | 5 | 5 | 5 | 5 |
111 | 5 | 5 | 5 | 5 | 5 | 5 |
112 | 5 | 5 | 5 | 5 | 5 | 5 |
113 | 5 | 5 | 5 | 5 | 5 | 5 |
114 | 5 | 5 | 5 | 5 | 5 | 5 |
115 | 5 | 5 | 5 | 5 | 5 | 5 |
116 | 5 | 5 | 5 | 5 | 5 | 5 |
117 | 5 | 5 | 5 | 5 | 5 | 5 |
118 | 5 | 5 | 5 | 5 | 5 | 5 |
119 | 5 | 5 | 5 | 5 | 5 | 5 |
120 | 5 | 5 | 5 | 5 | 5 | 5 |
121 | 5 | 5 | 5 | 5 | 5 | 5 |
122 | 5 | 5 | 5 | 5 | 5 | 5 |
123 | 5 | 5 | 5 | 5 | 5 | 5 |
124 | 5 | 5 | 5 | 5 | 5 | 5 |
125 | 5 | 5 | 5 | 5 | 5 | 5 |
126 | 5 | 5 | 5 | |||
127 | 5 | 5 | 5 | 5 | 5 | 5 |
128 | 5 | 5 | 5 | 5 | 5 | 5 |
129 | 5 | 5 | 5 | 5 | 5 | 5 |
130 | 5 | 5 | 5 | 5 | 5 | 5 |
131 | 5 | 5 | 5 | 5 | 5 | 5 |
132 | 5 | 5 | 5 | 5 | 5 | 5 |
133 | 5 | 5 | 5 | 5 | 5 | 5 |
134 | 5 | 5 | 5 | 5 | 5 | 5 |
135 | 5 | 5 | 5 | 5 | 5 | 5 |
136 | 5 | 5 | 5 | 5 | 5 | 5 |
139 | 5 | 5 | 5 | 5 | 5 | 5 |
140 | 5 | 5 | 5 | 5 | 5 | 5 |
141 | 5 | 5 | 5 | 5 | 5 | 5 |
142 | 5 | 5 | 5 | 5 | 5 | 5 |
143 | 5 | 5 | 5 | 5 | 5 | 5 |
144 | 5 | 5 | 5 | 5 | 5 | 5 |
145 | 5 | 5 | 5 | 5 | 5 | 5 |
146 | 5 | 5 | 5 | 5 | 5 | 5 |
147 | 5 | 5 | 5 | 5 | 5 | 5 |
148 | 5 | 5 | 5 | 5 | 5 | 5 |
149 | 5 | 5 | 5 | 5 | 5 | 5 |
150 | 5 | 5 | 5 | 5 | 5 | 5 |
151 | 5 | 5 | 5 | 5 | 5 | 5 |
152 | 5 | 5 | 5 | 5 | 5 | 5 |
153 | 5 | 5 | 5 | 5 | 5 | 5 |
154 | 5 | 5 | 5 | 5 | 5 | 5 |
155 | 5 | 5 | 5 | 5 | 5 | 5 |
156 | 5 | 5 | 5 | 5 | 5 | 5 |
157 | 5 | 5 | 5 | 5 | 5 | 5 |
158 | 5 | 5 | 5 | 5 | 5 | 5 |
159 | 5 | 5 | 5 | 5 | 5 | 5 |
160 | 5 | 5 | 5 | 5 | 5 | 5 |
161 | 5 | 5 | 5 | 5 | 5 | 5 |
化合物序号 | 籼稻 | 粳稻 | 抗ALS的稗草 | 抗ALS类的碎米莎草 |
3 | 0 | 0 | 5 | 5 |
4 | 0 | 0 | 5 | 5 |
7 | 0 | 0 | 5 | 5 |
66 | 0 | 0 | 5 | 5 |
74 | 0 | 0 | 5 | 5 |
77 | 0 | 0 | 5 | 5 |
79 | 0 | 0 | 5 | 5 |
82 | 0 | 0 | 5 | 5 |
87 | 0 | 0 | 5 | 5 |
88 | 0 | 0 | 5 | 5 |
97 | 0 | 0 | 5 | 5 |
98 | 0 | 0 | 5 | 5 |
130 | 0 | 0 | 5 | 5 |
对照化合物A(600克/公顷) | 3 | 3 | 5 | 5 |
对照化合物A(300克/公顷) | 2 | 3 | 4 | 4 |
双草醚(100克/公顷) | 2 | 4 | 1 | 1 |
化合物序号 | 水稻 | 鸭舌草 |
3 | 0 | 5 |
4 | 0 | 5 |
7 | 0 | 5 |
66 | 0 | 5 |
74 | 0 | 5 |
77 | 0 | 5 |
79 | 0 | 5 |
82 | 0 | 5 |
87 | 0 | 5 |
88 | 0 | 5 |
97 | 0 | 5 |
98 | 0 | 5 |
130 | 0 | 5 |
五氟磺草胺50克/公顷 | 1 | 1 |
Claims (10)
- 一种如式Ⅰ所示的吡啶氧基硫酯衍生物,其中,A、B分别独立地代表卤素,含有或不含有卤素的烷基或环烷基;C代表氢、卤素、烷基、卤代烷基;Q代表卤素,氰基,氰基烷基,羟基烷基,氨基,硝基,甲酰基,不含或含有卤素的烷基、烯基、炔基、环烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、烷基氨基烷基或烷氧基烷基,未取代或取代的芳基、杂芳基、芳基烷基、杂芳基烷基;R 3分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基以及未取代或取代的杂环基、芳基、杂芳基、杂环基烷基、芳基烷基、杂芳基烷基;R 4、R 5、R 6分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基羰基以及未取代或取代的杂环基、芳基、杂芳基、杂环基烷基、芳基烷基、杂芳基烷基;X代表硝基或NR 1R 2,其中R 1代表H,任选地可被1-2个R 11取代的烷基、烯基或炔基,-COR 12,硝基,OR 13,SO 2R 14,NR 15R 16,N=CR 17R 18,烷基氨基甲酰基,二烷基氨基甲酰基,三烷基甲硅烷基或二烷基膦酰基;R 2代表H,任选地可被1-2个R 11取代的烷基或-COR 12;或者NR 1R 2代表N=CR 21NR 22R 23,N=CR 24OR 25,未取代或被1-2个独立选自卤素、烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、氨基、烷基氨基、二烷基氨基、烷氧基羰基中的基团所取代的不含有或含有氧原子、硫原子或其它氮原子的5-或6-元饱和或不饱和环;其中R 11独立地代表卤素,羟基,烷氧基,卤代烷氧基,烷硫基,卤代烷硫基,氨基、烷基氨基,二烷基氨基,烷氧基羰基,未取代或取代的芳基、杂芳基;R 12代表H、烷基、卤代烷基、烷氧基、苯基、苯氧基或苄氧基;R 13代表H、烷基、卤代烷基、苯基、苄基或CHR 31C(O)OR 32;R 31代表H、烷基或烷氧基;R 32代表H、烷基或苄基;R 14代表烷基、卤代烷基;R 15代表H、烷基、甲酰基、烷基酰基、卤代烷基酰基、烷氧基羰基、苯基羰基、苯氧基羰基或苄氧基羰基;R 16代表H、烷基;R 21、R 24分别独立地代表H或烷基;R 22、R 23分别独立地代表H或烷基;或者NR 22R 23代表不含有或含有氧原子、硫原子或其它氮原子的5-或6-元饱和或不饱和环;R 25代表烷基。
- 根据权利要求1所述的吡啶氧基硫酯衍生物,其特征在于,A、B分别独立地代表卤素,含有或不含有卤素的C1-C8烷基或C3-C8环烷基;C代表氢、卤素、C1-C8烷基、卤代C1-C8烷基;Q代表卤素,氰基,氰基C1-C8烷基,羟基C1-C8烷基,氨基,硝基,甲酰基,不含或含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C1-C8烷氧基、C1-C8烷硫基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷基氨基C1-C8烷基或C1-C8烷氧基C1-C8烷基,未取代或取代的芳基、杂芳基、芳基C1-C8烷基、杂芳基C1-C8烷基;R 3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烷基以及未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C8烷基、芳基C1-C8烷基、杂芳基C1-C8烷基;R 4、R 5、R 6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、C1-C8烷氧基羰基以及未取代或取代的杂环基C1-C8烷基、芳基C1-C8烷基、杂芳基C1-C8烷基;X代表硝基或NR 1R 2,其中R 1代表H,任选地可被1-2个R 11取代的C1-C8烷基、C2-C8烯基或C2-C8炔基,-COR 12,硝基,OR 13,SO 2R 14,NR 15R 16,N=CR 17R 18,C1-C8烷基氨基甲酰基,二C1-C8烷基氨基甲酰基,三C1-C8烷基甲硅烷基或二C1-C8烷基膦酰基;R 2代表H,任选地可被1-2个R 11取代的C1-C8烷基或-COR 12;或者NR 1R 2代表N=CR 21NR 22R 23,N=CR 24OR 25,未取代或被1-2个独立选自卤素、C1-C8烷基、C1-C8烷氧基、卤代C1-C8烷氧基、C1-C8烷硫基、卤代C1-C8烷硫基、氨基、C1-C8烷基氨基、二C1-C8烷基氨基、C1-C8烷氧基羰基中的基团所取代的其中R 11独立地代表卤素,羟基,C1-C8烷氧基,卤代C1-C8烷氧基,C1-C8烷硫基,卤代C1-C8烷硫基,氨基,C1-C8烷基氨基,二C1-C8烷基氨基,C1-C8烷氧基羰基,未取代或被卤素、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基、硝基中的1-3个基团所取代的苯基、萘基、R 12代表H、C1-C18烷基、卤代C1-C8烷基、C1-C8烷氧基、苯基、苯氧基或苄氧基;R 13代表H、C1-C8烷基、卤代C1-C8烷基、苯基、苄基或CHR 31C(O)OR 32;R 31代表H、C1-C8烷基或C1-C8烷氧基;R 32代表H、C1-C8烷基或苄基;R 14代表C1-C8烷基、卤代C1-C8烷基;R 15代表H、C1-C8烷基、甲酰基、C1-C8烷基酰基、卤代C1-C8烷基酰基、C1-C8烷氧基羰基、苯基羰基、苯氧基羰基或苄氧基羰基;R 16代表H、C1-C8烷基;R 21、R 24分别独立地代表H或C1-C8烷基;R 25代表C1-C8烷基;所述“杂环基”是指具有0、1或2个氧代基团的 所述“芳基”是指苯基、萘基;所述“杂芳基”是指 其中,其被选自卤素,硝基,氰基,氰硫基,羟基,羧基,巯基,甲酰基,未取代或被选自卤素、烷基、烷氧基中的至少一个基团所取代的苯基、苄基、苄氧基、苯氧基,含有或不含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、OR”、SR”、-烷基-OR”、-烷基-SR”、COR”、COOR”、COSR”、SOR”、SO 2R”、OCOR”、SCOR”,以及被选自氢、烷基、烯基、炔基、环烷基、环烷基烷基、苯基、苄基、苄氧基、苯氧基、COR”、COOR”、SO 2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基中的至少一个基团所取代;R’分别独立地代表氢,硝基,羟基,氨基,含有或不含有卤素的烷基、烯基、炔基、环烷基、环烯基、环烷基烷基、烷氧基、烯基氧基、炔基氧基、环烷基氧基、烷氧基烷基、烷氧基羰基、烷硫基羰基、烷基磺酰基、烷基磺酰基烷基、烷基羰基、烷基羰基烷基、烷基酰氧基、烷基氨基、烷基氨基羰基、烷氧基氨基羰基、烷氧基羰基烷基、烷氨基羰基烷基、三烷基甲硅烷基、二烷基膦酰基;R”分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基。
- 根据权利要求2所述的吡啶氧基硫酯衍生物,其特征在于,A、B分别独立地代表卤素,含有或不含有卤素的C1-C6烷基或C3-C6环烷基;C代表氢、卤素、C1-C6烷基、卤代C1-C6烷基;Q代表卤素,氰基,氰基C1-C6烷基,羟基C1-C6烷基,氨基,硝基,甲酰基,不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基C1-C6烷基或C1-C6烷氧基C1-C6烷基,未取代或取代的芳基、杂芳基、芳基C1-C6烷基、杂芳基C1-C6烷基;R 3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烷基以及未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C6烷基、芳基C1-C6烷基、杂芳基C1-C6烷基;R 4、R 5、R 6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、C1-C6烷氧基羰基以及未取代或取代的杂环基C1-C6烷基、芳基C1-C6烷基、杂芳基C1-C6烷基;X代表硝基或NR 1R 2,其中R 1代表H,任选地可被1-2个R 11取代的C1-C6烷基、C2-C6烯基或C2-C6炔基,-COR 12,硝基,OR 13,SO 2R 14,NR 15R 16,N=CR 17R 18,C1-C6烷基氨基甲酰基,二C1-C6烷基氨基甲酰基,三C1-C6烷基甲硅烷基或二C1-C6烷基膦酰基;R 2代表H,任选地可被1-2个R 11取代的C1-C6烷基或-COR 12;或者NR 1R 2代表N=CR 21NR 22R 23,N=CR 24OR 25,未取代或被1-2个独立选自卤素、C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、氨基、C1-C6烷基氨基、二C1-C6烷基氨基、C1-C6烷氧基羰基中的基团所取代的其中R 11独立地代表卤素,羟基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,氨基,C1-C6烷基氨基,二C1-C6烷基氨基,C1-C6烷氧基羰基,未取代或被卤素、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、硝基中的1-3个基团所取代的苯基、萘基、R 12代表H、C1-C14烷基、卤代C1-C6烷基、C1-C6烷氧基、苯基、苯氧基或苄氧基;R 13代表H、C1-C6烷基、卤代C1-C6烷基、苯基、苄基或CHR 31C(O)OR 32;R 31代表H、C1-C6烷基或C1-C6烷氧基;R 32代表H、C1-C6烷基或苄基;R 14代表C1-C6烷基、卤代C1-C6烷基;R 15代表H、C1-C6烷基、甲酰基、C1-C6烷基酰基、卤代C1-C6烷基酰基、C1-C6烷氧基羰基、苯基羰基、苯氧基羰基或苄氧基羰基;R 16代表H、C1-C6烷基;R 21、R 24分别独立地代表H或C1-C6烷基;R 25代表C1-C6烷基;所述“杂环基”是指具有0、1或2个氧代基团的 所述“芳基”是指苯基、萘基;所述“杂芳基”是指 其中,其被选自卤素,硝基,氰基,氰硫基,羟基,羧基,巯基,甲酰基,未取代或被选自卤素、C1-C6烷基、C1-C6烷氧基中的至少一个基团所取代的苯基、苄基、苄氧基、苯氧基,含有或不含有卤素的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、OR”、SR”、-(C1-C6)烷基-OR”、-(C1-C6)烷基-SR”、COR”、COOR”、COSR”、SOR”、SO 2R”、OCOR”、SCOR”,以及被选自氢、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、苯基、苄基、苄氧基、苯氧基、COR”、COOR”、SO 2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基中的0、1、2或3个基团所取代;R’分别独立地代表氢,硝基,羟基,氨基,含有或不含有氟、氯、溴的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烯基、C3-C6环烷基C1-C6烷基、C1-C6烷氧基、C2-C6烯基氧基、C2-C6炔基氧基、C3-C6环烷基氧基、C1-C6烷氧基C1-C6烷基、C1-C6烷氧基羰基、C1-C6烷硫基羰基、C1-C6烷基磺酰基、C1-C6烷基磺酰基C1-C6烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷基酰氧基、C1-C6烷基氨基、C1-C6烷基氨基羰基、C1-C6烷氧基氨基羰基、C1-C6烷氧基羰基C1-C6烷基、C1-C6烷氨基羰基C1-C6烷基、三C1-C6烷基甲硅烷基、二C1-C6烷基膦酰基;R”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。
- 根据权利要求3所述的吡啶氧基硫酯衍生物,其特征在于,A、B分别独立地代表卤素、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基;C代表氢、卤素、C1-C6烷基、卤代C1-C6烷基;Q代表C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、C2-C6烯基、C2-C6炔基、卤素、氰基、氨基、硝基、甲酰基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氧羰基、羟基C1-C6烷基、C1-C6烷氧基C1-C2烷基、氰基C1-C2烷基、C1-C6烷氨基C1-C2烷基、苄基、萘基、呋喃基、噻吩基、噻唑基、吡啶基、嘧啶基,以及未取代或被C1-C6烷基取代的 未取代或被C1-C6烷基、卤代C1-C6烷基、卤素和C1-C6烷氧基中的至少一个基团所取代的苯基;M代表C1-C12烷基、卤代C1-C8烷基、C3-C6环烷基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷氧羰基、C1-C6烷基磺酰基、氰基C1-C6烷基、硝基C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6烷氧羰基C1-C6烷基、C2-C6烯氧基羰基C1-C6烷基、-(C1-C6烷基)-R、 四氢呋喃基、吡啶基、萘基、呋喃基、噻吩基、 以及未取代或C1-C6烷基取代的 未取代或被C1-C6烷基、卤代C1-C6烷基、C1-C6烷基氨基、卤素或C1-C6烷氧基取代的苯基;R 3分别独立地代表C1-C6烷基;R 4、R 5、R 6分别独立地代表氢、C1-C6烷基、C1-C6烷氧基羰基;R’代表C1-C6烷基、卤代C1-C6烷基;X代表氨基、C1-C6烷基氨基、C1-C6烷基羰基氨基、苯基羰基氨基、苄基氨基、未取代或卤代C1-C6烷基取代的呋喃基亚甲基氨基。
- 根据权利要求4所述的吡啶氧基硫酯衍生物,其特征在于,A、B分别独立地代表氟、氯、溴、碘、甲基、乙基、丙基、异丙基、三氟甲基、环丙基;C代表氢、氟、氯、溴、碘、甲基、三氟甲基;Q代表甲基、乙基、丙基、异丙基、环丙基、乙烯基、乙炔基、氟、氯、溴、氰基、氨基、硝基、甲酰基、甲氧基、甲硫基、甲氧羰基、一氯甲基、一氟甲基、二氟甲基、三氟甲基、2-氯乙基、2,2,2-三氟乙基、羟基甲基、 苄基、萘基、呋喃基、噻吩基、噻唑基、吡啶基、嘧啶基,以及未取代或被甲基取代的 未取代或被甲基、三氟甲基、氯和甲氧基中的至少一个基团所取代的苯基;R’代表甲基、乙基、二氟甲基;M代表甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、三氟甲基、五氟乙基、3-氯丁基、2-氟乙基、2-氯乙基、2-溴乙基、2,2-二氟乙基、2,2,2-三氟乙基、4,4,4-三氟丁基、2,2,3,3,3-五氟丙基、环丙基、环丁基、环戊基、环己基、烯丙基、2-丙炔基、甲氧基、乙氧羰基、甲基磺酰基、 四氢呋喃基、吡啶基、萘基、呋喃基、噻吩基、 以及未取代或甲基取代的 未取代或被甲基、二甲基氨基、氯、甲氧基、三氟甲基或异丙基取代的苯基;
- 根据权利要求5所述的吡啶氧基硫酯衍生物,其特征在于,其选自表1中的任意一个。
- 一种如权利要求1-6任意一项所述的吡啶氧基硫酯衍生物的制备方法,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通式I所示的化合物;其反应方程式如下:其中,W代表碱金属,优选K、Na;Hal代表卤素,优选Br、Cl;所述反应在催化剂和溶剂的存在下进行,优选地,所述催化剂为TBAB,所述溶剂为DCM、DCE、ACN、THF、DMF中的一种或多种组合;其中,卤代物优选氯代物或溴代物;所述反应在碱和溶剂的存在下进行,所述碱选自氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸铯中的一种或两种以上;溶剂选自THF、1,4-二氧六环、甲苯、1,2-二氯乙烷、乙酸乙酯、乙腈、DMF、丙酮、二氯甲烷和氯仿中的一种或多种组合;所述反应过程中也可加入催化剂,优选DMAP。
- 一种除草组合物,其特征在于,包括(i)权利要求1-6任意一项所述的吡啶氧基硫酯衍生物中的至少一种;优选地,还包括(ii)一种或多种另外的除草剂和/或安全剂;更优选地,还包括(iii)农业化学上可接受的制剂助剂。
- 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任意一项所述的吡啶氧基硫酯衍生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,优选地,所述植物为水稻(如粳稻、籼稻),所述杂草为禾本科(如稗草、马唐、千金子、狗尾草)、阔叶草(如苘麻、鸭舌草)和莎草科杂草(如碎米莎草)。
- 如权利要求1-6任意一项所述的吡啶氧基硫酯衍生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,将所述的吡啶氧基硫酯衍生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,更优选地,所述作物为水稻(如粳稻、籼稻),所述杂草为禾本科(如稗草、马唐、千金子、狗尾草)、阔叶草(如苘麻、鸭舌草)和莎草科杂草(如碎米莎草)。
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