WO2020108518A1 - N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or salt thereof, preparation method therefor, herbicidal composition and use thereof - Google Patents
N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or salt thereof, preparation method therefor, herbicidal composition and use thereof Download PDFInfo
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- WO2020108518A1 WO2020108518A1 PCT/CN2019/121224 CN2019121224W WO2020108518A1 WO 2020108518 A1 WO2020108518 A1 WO 2020108518A1 CN 2019121224 W CN2019121224 W CN 2019121224W WO 2020108518 A1 WO2020108518 A1 WO 2020108518A1
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- alkyl
- cycloalkyl
- group
- aryl
- substituted
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Links
- 0 C[*+]N1CCCC1 Chemical compound C[*+]N1CCCC1 0.000 description 3
- VUXKEHWALDRLPQ-UHFFFAOYSA-N CCCC1=CCOC1 Chemical compound CCCC1=CCOC1 VUXKEHWALDRLPQ-UHFFFAOYSA-N 0.000 description 1
- VQKFNUFAXTZWDK-UHFFFAOYSA-N Cc1ccc[o]1 Chemical compound Cc1ccc[o]1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Definitions
- the invention belongs to the technical field of pesticides, and specifically relates to an N-(1,3,4-oxadiazol-2-yl)aryl formamide or a salt thereof, a preparation method, a herbicidal composition and applications.
- WO2014086746A1 discloses some aryl formamides Compounds and their use as herbicides.
- chiral herbicides have been developed on the market, such as aryloxyphenoxypropionic acid herbicides quizalofop, pirfenachlor, cyflufenazone, oxaflufen, and oxacox Carbendazim; aryloxypropionic acid herbicides 2 methyl 4-chloropropionic acid, 2,4-D propionic acid; chloroamide herbicide S metolachlor, the development of these chiral herbicides has greatly reduced The use of invalid bodies provides a higher guarantee for environmental safety, but there has never been commercialization of sulfur-containing chiral herbicides, and this application has surprisingly discovered sulfur-chiral herbicides of aryl formamide compounds , With huge commercial value.
- the invention provides an N-(1,3,4-oxadiazol-2-yl)aryl formamide or its salt, a preparation method, a herbicidal composition and an application, the amount of the compound is low, and the herbicidal activity Excellent, and with higher crop safety, especially for rice and other key crops to establish a good selectivity.
- X represents O, S, SO, SO 2 or NR 1 ;
- Z represents hydrogen, halogen, cyano, OR 4 , -alkyl-OR 4 , -O-alkyl-N(R 5 ) 2 , -alkyl-O-alkyl-N(R 5 ) 2 , N( R 5 ) 2 ,-alkyl-(C ⁇ O) m -N(R 5 ) 2 ,-NH-alkyl-N(R 5 ) 2 , alkyl, alkenyl, alkynyl groups that do not contain or contain halogen , Alkoxycarbonyl, alkoxycarbonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, unsubstituted or substituted Cycloalkyl, unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl,
- M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -alkyl -R, alkyl group, alkenyl group, alkynyl group, cycloalkyl group not containing or containing halogen, and unsubstituted or substituted arylalkyl group, heteroarylalkyl group;
- R 4 , R 6 , and R 11 independently represent hydrogen, an alkyl group containing no or halogen, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, alkoxyalkyl group, and Unsubstituted or substituted heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl, heteroaryl Oxyalkyl;
- R 3 and R 12 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, alkoxyalkyl, and unsubstituted or substituted Heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl;
- R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , alkyl, haloalkyl, alkenyl, haloalkenyl , Alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryl Oxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl,
- R 21 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;
- R 22 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;
- n and r independently represent 0, 1 or 2;
- X represents O, S, SO, SO 2 or NR 1 ;
- Y represents halogen, cyano, cyano C1-C8 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C8)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C8) alkyl -CON (R 2) 2, - (C1-C8) alkyl -N (R 2) 3 + I -, hydroxy C1-C8 alkyl, substituted amino and carboxyl C1- C8 alkyl, OR 3 , SR 3 , -(C1-C8)alkyl-SOR 3 , -(C1-C8)alkyl-OR 3 , -(C1-C8)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C8)alkyl-COR 4 ,-(C1-C8)alkyl-COOR 4 ,-(C1-C8)alkyl-OCOR 3 ,
- -XY represents unsubstituted or selected by halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or substituted by at least one group selected from halogen, alkyl, alkoxy Substituted phenyl, benzyl, phenoxy, and alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkoxyalkyl with or without halogen Substituted by at least one group of alkyl, alkylthioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylacyloxy of
- M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C8 alkyl)-R, C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and unsubstituted or substituted aryl C1-C8 Alkyl, heteroaryl C1-C8 alkyl;
- R 4 , R 6 , and R 11 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkane C1-C8 alkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy C1-C8 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C8 alkyl, heterocyclyloxy C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryloxy C1-C8 alkyl, heteroaryl, heteroaryl C1-C8 alkyl, heteroaryloxy C1-C8 alkyl ;
- R 3 and R 12 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, C3-C8 cycloalkenyl group, C1-C8 alkoxy C1-C8 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C8 alkyl group, aryl group, aryl C1-C8 alkyl group , Heteroaryl, heteroaryl C1-C8 alkyl;
- R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C8 alkyl, halogenated C1-C8 alkyl , C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, halogenated C3-C8 cycloalkane Group, C1-C8 alkoxy C1-C8 alkyl, C3-C8 cycloalkyl C1-
- R 21 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;
- R 22 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;
- n and r independently represent 0, 1 or 2;
- heterocyclic group refers to a group having 0, 1, or 2 oxo groups
- aryl refers to phenyl and naphthyl
- heteroaryl refers to
- halogen nitro, cyano, cyanothio, hydroxy, carboxy, mercapto, formyl, unsubstituted or selected from at least one group selected from halogen, alkyl, alkoxy Phenyl, benzyl, phenoxy substituted by groups, with or without halogen alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, OR", SR", -alkyl-OR ", -alkyl-SR", COR”, COOR", COSR", SOR", SO 2 R", OCOR", SCOR" are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, Amino or aminocarbonyl substituted by one or two groups of cycloalkylalkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2
- 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 or alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl with or without halogen.
- X represents O, S, SO, SO 2 or NR 1 ;
- Y represents halogen, cyano, cyano C1-C6 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C6)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C6) alkyl -CON (R 2) 2, - (C1-C6) alkyl -N (R 2) 3 + I -, hydroxy C1-C6 alkyl, substituted amino and carboxyl C1- C6 alkyl, OR 3 , SR 3 , -(C1-C6)alkyl-SOR 3 , -(C1-C6)alkyl-OR 3 , -(C1-C6)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C6)alkyl-COR 4 ,-(C1-C6)alkyl-COOR 4 ,-(C1-C6)alkyl-OCOR 3 ,
- -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 with or without halogen Cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1- C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfiny
- M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C6 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C1-C6 unsubstituted or substituted aryl Alkyl, heteroaryl C1-C6 alkyl;
- R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C6 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C6 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C6 alkyl, heterocyclyloxy C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy C1-C6 alkyl ;
- R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C6 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C6 alkyl group, aryl group, aryl C1-C6 alkyl group , Heteroaryl, heteroaryl C1-C6 alkyl;
- R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkane Group, C1-C6 alkoxy C1-C6 alkyl, C3-C6 cycloalkyl C1-
- R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;
- R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;
- n and r independently represent 0, 1 or 2;
- heterocyclic group refers to a group having 0, 1, or 2 oxo groups
- aryl refers to phenyl and naphthyl
- heteroaryl refers to
- halogen selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl , C3-C8 cycloalkyl C1-C8 alkyl, OR", SR", -(C1-C8)alkyl-OR", -(C1-C8)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 alk
- R'independently represents hydrogen, nitro, hydroxy, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, with or without fluorine, chlorine, or bromine C3-C8 cycloalkenyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy , C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthiocarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylsulfonyl C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyl C1-C8
- R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl with or without halogen .
- X represents O, S, SO, SO 2 or NR 1 ;
- Y represents halogen, cyano, cyano C1-C2 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C2)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C2) alkyl -CON (R 2) 2, - (C1-C2) alkyl -N (R 2) 3 + I -, hydroxy C1-C2 alkyl, substituted amino and carboxyl C1- C2 alkyl, OR 3 , SR 3 , -(C1-C2)alkyl-SOR 3 , -(C1-C2)alkyl-OR 3 , -(C1-C2)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C2)alkyl-COR 4 ,-(C1-C2)alkyl-COOR 4 ,-(C1-C2)alkyl-OCOR 3 ,
- -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxyl, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 with or without halogen Cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkylthio C1- C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfin
- M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C2 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and unsubstituted or substituted aryl C1-C2 Alkyl, heteroaryl C1-C2 alkyl;
- R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C2 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C2 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C2 alkyl, heterocyclyloxy C1-C2 alkyl, aryl, aryl C1-C2 alkyl, aryloxy C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryloxy C1-C2 alkyl ;
- R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C2 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C2 alkyl group, aryl group, aryl C1-C2 alkyl group , Heteroaryl, heteroaryl C1-C2 alkyl;
- R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkane Group, C1-C6 alkoxy C1-C2 alkyl, C3-C6 cycloalkyl C1-
- R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;
- R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;
- n and r independently represent 0, 1 or 2;
- heterocyclic group refers to a group having 0, 1, or 2 oxo groups
- aryl refers to phenyl and naphthyl
- heteroaryl refers to
- halogen selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl , C3-C6 cycloalkyl C1-C2 alkyl, OR", SR", -(C1-C2)alkyl-OR", -(C1-C2)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6
- 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-C8 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy , C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C2 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 or C3-C6 cycloalkyl C1-C2 alkyl with or without halogen .
- X represents S, SO or SO 2 ;
- Y represents C2-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy C1-C8 alkyl, hydroxy C1-C8 alkyl, cyano, Cyano C1-C8 alkyl, amino C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, di-C1-C8 alkylaminocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy C1- C8 alkyl, C1-C8 alkyl
- heterocyclic group is Heteroaryl is unsubstituted or substituted by C1-C8 alkyl
- R"' independently represents C1-C8 alkyl
- Z represents hydrogen, C1-C8 alkyl
- M represents hydrogen, C1-C8 alkoxycarbonyloxy C1-C8 alkyl
- X represents S, SO or SO 2 ;
- Y represents C2-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, hydroxy C1-C6 alkyl, cyano, Cyano C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, di-C1-C6 alkylaminocarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy C1- C6 alkyl, C1-C6 alkyl
- heterocyclic group is Heteroaryl is unsubstituted or substituted with C1-C6 alkyl
- R"' independently represents C1-C6 alkyl
- Z represents hydrogen, C1-C6 alkyl
- M represents hydrogen, C1-C6 alkoxycarbonyloxy C1-C6 alkyl.
- the compound is preferably The definition of the groups Y, Z and M is as described above.
- 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 )- and so on.
- the alkyl group is, 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 Group, 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, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butylene -3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl.
- Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of 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 having, for example, three to six carbocyclic members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where the double bond can be at any position.
- Halogen is fluorine, chlorine, bromine or iodine.
- the "aryl" in the present invention includes but is not limited to phenyl, naphthyl, Heterocyclyl is a cyclic group containing 3 to 6 ring atoms, which can also be fused through a benzo ring, saturated, partially saturated or completely unsaturated, 1 to 4 of the ring atoms (eg 1, 2, 3, 4) heteroatoms are selected from oxygen, nitrogen and sulfur.
- heterocyclic groups include but are not limited to those with 0, 1 or 2 oxo groups
- Heteroaryl is an aromatic cyclic group containing, for example, 3 to 6 ring atoms and also fused through a benzo ring, 1 to 4 of the ring atoms (e.g. 1, 2, 3, 4) Heteroatoms are selected from oxygen, nitrogen and sulfur.
- heteroaryl is R'is as defined above.
- 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, such as the four R 2 groups in “N(R 2 ) 2 "and “-alkyl-N(R 2 ) 2 "
- the groups are independently selected from those mentioned in R 2 and may be the same or different.
- the three R 3 groups in “Si(R 3 ) 3 ” are independently selected from those mentioned in R 3 , May be the same or different.
- multiple parallel substituents in the present invention have the above-mentioned qualifiers for each subsequent substituent, such as “free or containing halogen” "Alkyl, alkenyl, alkynyl, cycloalkyl” in the “free or containing halogen” has a limiting role for each subsequent group “alkyl” “alkenyl” “alkynyl” “cycloalkyl” .
- the salt derivative is a salt used in general pesticides, for example, it can be made into a metal salt, an amine salt, a sulfonium salt or a phosphonium salt, or, when there is a basic part in the molecule, it can be made into a sulfate salt Salts of acid salts, nitrates, phosphates, etc. These salts are also included in the present invention as long as they are used as herbicides for agriculture and horticulture.
- the "metal salt” may be, for example, an alkali metal salt, an alkaline earth metal salt, an aluminum salt, or an iron salt.
- alkali metal salt may be, for example, a sodium salt, a potassium salt or a lithium salt, preferably a sodium salt or a potassium salt.
- the "alkaline earth metal salt” may be, for example, a calcium salt or a magnesium salt, preferably a calcium salt.
- the "amine salt” may be, for example, a secondary alkyl amine salt, a tertiary alkyl amine salt or a quaternary alkyl amine salt; Quaternary amine salt; primary alkyl alkoxy salt, secondary alkyl amine salt, tertiary alkyl amine salt or quaternary alkyl amine salt; or primary alkoxy alkoxy salt, alkoxy alkane Alcohol secondary amine salts, alkoxyalkanol tertiary amine salts or alkoxyalkanol quaternary amine salts, preferably, wherein the alkyl, alkanol and alkoxy groups are independently saturated and independently contain C1-C4 Carbon atoms, which may also be substituted by phenyl and/or halogen, more preferably monoethanolamine salt, dimethylethanolamine salt, triethanolamine salt, dimethylamine salt, triethylamine salt, isopropylamine salt, choline salt,
- Solvates of the compounds of the invention are also included in the invention.
- the compounds of general formula I may exist as stereoisomers. For example, if one or more asymmetric carbon or sulfur 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.
- a method for preparing the N-(1,3,4-oxadiazol-2-yl)aryl formamide compound includes the following steps:
- the preparation method includes the following steps:
- Q stands for O, S or NR 1 ;
- the reaction in the step (1) is performed in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of NaOH and KOH, and the solvent is selected from DMF, DCM, DCE , ACN, THF, TFA one or more combinations; the reaction temperature is 0 ⁇ 25 °C;
- the reaction in the step (2) is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is n-butyl lithium, and the solvent is selected from one or more of THF, DMF, DCM, DCE, ACN, and TFA Combinations; the reaction temperature is -100 ⁇ -50 °C;
- the reaction in the step (3) is carried out in the presence of a halogenating agent, a catalyst and a solvent; preferably, the halogenating agent is SOCl 2 , the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine; the reaction The temperature is 0 ⁇ 50°C.
- the compound represented by the general formula I-2 is prepared according to the above preparation method of the compound represented by the general formula I-1, and then a dealkylation reaction is performed; preferably, the reaction is in the presence of a solvent; more preferably, The solvent is selected from one or more combinations of DCM, DCE, ACN, DMF, THF, and TFA; the reaction temperature is 20-120°C; and then the prepared compound represented by general formula VII and Hal -Y reaction to prepare a compound represented by general formula I-3; preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate
- the solvent is selected from one or more combinations of DCM, DCE, ACN, THF, and DMF; the reaction temperature is 0-25°C;
- Hal represents halogen, preferably fluorine, chlorine or bromine.
- the compound represented by the general formula I-3 is reacted with peroxide to prepare the compound represented by the general formula I-4 and/or I-5;
- the peroxide is The reaction is carried out in the presence of a solvent; more preferably, the solvent is selected from one or a combination of DCM and DCE; and the reaction temperature is 0-50°C.
- the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate, and the solvent is selected from DCM, DCE, ACN, THF , DMF one or more combinations, the reaction temperature is 0 ⁇ 100 °C;
- the reaction is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is 4-dimethylaminopyridine, the solvent is pyridine, and the reaction temperature is 0-80°C.
- a herbicidal composition comprising (i) an N-(1,3,4-oxadiazol-2-yl)aryl formamide compound represented by general formula I; preferably, it also includes (ii) One or more additional herbicides and/or safeners; more preferably, (iii) agrochemically acceptable formulation aids.
- the additional herbicides include the following compounds or their derivatives such as salts and esters:
- ALS inhibitors pyrazosulfuron-methyl (cas No.: 93697-74-6), penoxsulam (cas No.: 219714-96-2), bischlorfen (cas No.: 125401-92-5) , Pyrachlor (cas No.: 147411-69-6), pyrazosulfuron (cas No.: 868680-84-6), promethazine (cas No.: 570415-88-2), fluoromethoxazole Oxachlor (cas number: 874195-61-6);
- ACCase inhibitors cyflufenazone (cas No.: 122008-85-9), oxacarfen (cas no.: 256412-89-2);
- Hormone inhibitors quinclorac (cas number: 84087-01-4), 2 methyl 4 chloro (cas number: 94-74-6), 2,4-D (cas number: 94-75- 7), 2,4-D butyric acid (cas number: 94-82-6), chlorofluoropyridine acetic acid (cas number: 69377-81-7), chlorofluoropyridine ester (cas number: 1390661-72-9 ), 2 methyl 4 chlorobutyric acid (cas number: 94-81-5), dicamba (cas number: 1918-00-9), diclofenac (cas number: 130901-36-8), dichloro Picolinic acid (cas number: 1702-17-6), triclofenac (cas number: 55335-06-3);
- Lipid synthesis (non-ACC) inhibitors Hecaodan (cas No.: 28249-77-6), Hecao Di (cas no.: 2212-67-1);
- HPPD inhibitors chlorfenapyr (cas No.: 1911613-97-2), chlorfenapyr (cas No.: 1622908-18-2), ciprofloxan (cas No.: 1855929-45 1), mesotrione (cas No.: 104206-82-8), bicyclosulone (cas no.: 156963-66-5), furan sulcotrione (cas no.: 473278-76-1);
- PDS inhibitors flufluramide (cas number: 83164-33-4), fluroxypyr (cas number: 61213-25-0), flubutachlor (cas number: 113614-08- 7);
- PPO inhibitors chlorfenapyr (cas number: 128621-72-7), bisaclostrile (cas number: 158353-15-2), oxadiazon (cas number: 19666-30-9), propionic Oxachlor (cas No.: 39807-15-3), oxyfluorfen (cas No.: 42874-03-3), cyclopentachlor (cas No.: 110956-75-7);
- PSIIinhibitors Xicaojing (cas No.: 1014-70-6), promethazin (cas no.: 7287-19-6), azatrochlor (cas no.: 129909-90-6), iso Binglong (cas No.: 34123-59-6), herbicide (cas no.: 314-40-9), dacao te (cas no.: 55512-33-9), chloromeron (cas no.: 15545-48 -9), bentazone (cas No.: 25057-89-0), diarrhea (cas No.: 709-98-8), diazepam (cas No.: 21087-64-9), atrazine (cas No.: 1912-24-9), bromoxynil (cas number: 1689-84-5), octanoyl bromoxynil (cas number: 1689-99-2), terbutin (CAS number: 5915-41- 3);
- DOXP inhibitor clomazone (cas number: 81777-89-1);
- salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
- 2,4-D or 2,4-D butyric acid derivatives include but are not limited to: 2,4-D or 2,4-D butyrate such as sodium salt, potassium salt, dimethylammonium salt, triethanol Ammonium salts, isopropylamine salts, choline, etc., and 2,4-D or 2,4-D butyrate esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.;
- 2 methyl 4 chloro derivatives include but not Limited to: 2 methyl 4 chloro sodium salt, potassium salt, dimethyl ammonium salt, isopropyl amine salt, etc., and 2 methyl 4 chloro methyl ester, ethyl ester, isooctyl ester, eth
- a method for controlling weeds which comprises weeding an effective amount of at least one of the N-(1,3,4-oxadiazol-2-yl)arylformamide compounds or the herbicide
- the agent composition is used on plants or weed areas.
- the plant is rice (such as indica rice, japonica rice), and the weed is gramineous weed (such as rice barnyardgrass, Qianjinjin, barnyard grass, horse tang, Setaria), broad-leaved weeds (such as gazania, wild mushrooms, velvetleaf, amaranth, chickweed), sedge weeds (such as sedge, fireflies).
- the use of at least one of the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compounds or the herbicide composition for controlling weeds preferably, The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound is used to control weeds in useful crops, which are genetically modified crops or genome editing techniques
- the crops are rice (such as indica rice, japonica rice)
- the weeds are gramineous weeds (such as rice barnyardgrass, Qianjin, barnyardgrass, crabgrass, green bristlegrass), broad-leaved weeds (such as duckweed , Wild champignons, velvetleaf, Amaranthus retroflexus, Stellaria), sedge grass weeds (such as sedge, firefly).
- the compounds of formula I according to the invention have outstanding herbicidal activity.
- the active substances of the present invention are 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 where the active substance works effectively include monocotyledons: annual oats, rye, grass, 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 Swine, 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, Cicus, Alisma, water chestnut, cane grass, and sedge, under such predetermined conditions as rice seeding.
- the weed seedlings can be completely prevented before the weeds grow, or they can stop growing when the weeds 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 grass, Ono sesame, Polygonum sibiricum, Stellaria, Ivy leaf Pompa, Arab Pompa, Pansy and Amaranthus, Swamp, and Kochia .
- the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are 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 usually 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 or salts thereof of the present invention 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 beets, 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 resistant 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-mentioned 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 active substance of the present invention When using the active substance of the present invention on genetically modified crops, in addition to the observable effects on other crops of suppressing harmful plants, there will often be special effects on the corresponding genetically modified crops, for example, to improve or expand control
- 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. Marsden's “Solvent Guide” Second Edition, Interscience, NY1963; McCutcheon's "Detergents and Emulsifiers” Annual Report, MC Publishing Company, Ridgewood NJ; Sisley and Wood, “Surface Encyclopedia", Chemical Publishing Company, NY1964; of [Ethylene oxide adduct surfactant], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler's "Chemische TECH” [Chemical Process], Volume 7, C. Hauser Verlag Kunststoff, 4th edition 1986.
- Wettable powders can be uniformly dispersed in water.
- they also include diluents or inert substances, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, poly Ethoxy fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2,2'-dinaphthyl methane Sodium -6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoyl methyl taurine.
- the active substances of the herbicides are finely ground, for example using commonly used equipment, such as hammer mills, fan mills and jet mills, and the adjuvants are mixed simultaneously or sequentially.
- Dissolve the active substance in an organic solvent to prepare a concentrated emulsion, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and add one more One or more ionic and/or nonionic surfactants (emulsifiers).
- a concentrated emulsion such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents.
- 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, for example, 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.
- 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 .
- the content of the active substance in the water-suspended granules mainly depends on whether the active substance is liquid or solid, and the additives, 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 substances 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.
- 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, propachlor, metolachlor, sinoprofen, alachlor, alachlor, toxachlor, cyproteron, naproxen, R-levonal Alachlor, Dipropanil, fenclofen, difenochlor, fenfluramide, alafenamide, flufenacetamide, bromobutanil, dimethyl thiazopyr, high-efficiency dimethyl Tetrachlor, ethoxyfen, chlorf
- the commercially available formulations are diluted in a 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.
- Table A2 is constructed in the same manner as Table A1, except that the entries below the "Z” column are replaced by the corresponding "Z" column entries shown below. Therefore, the first entry in Table A2 is compound 2-1 (where X is S, Y is Me, Z is Et, and M is H), followed by compound 2-2, compound 2-3, compound 2-4 ...The last entry is compound 2-661. Tables A3 to A152 are constructed similarly.
- Compound 1-136 was prepared by the above synthesis method of compound 1-4, then 1-136 (0.34 g, 1.0 mmol, 1.0 eq) was added to 5 mL of TFA, and then the reaction solution was stirred at 90°C 16 hours. The product was detected by LCMS and spin-dried to give A (0.29g) (yellow oil, crude).
- aqueous phase was extracted once with 50 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried, and separated by column chromatography to obtain g (3.0 g, 90% yield) (colorless oil).
- aqueous phase was extracted once with 50 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried, and separated by column chromatography to obtain j (3.1 g, 92% yield) (colorless oil).
- the standard of activity level of 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.
- Control Compound A N means some data is missing.
- compound 1-4 is more active than compound 1-1 and compound 1-5 than compound 1-2 on major grass weeds (such as rice field major grass weed barnyardgrass, Qianjin or horse tang).
- major grass weeds such as rice field major grass weed barnyardgrass, Qianjin or horse tang.
- compound 1-8 is much higher than compound 1-2, and when the carbon number exceeds 8, its activity decreases significantly, but the change in the number of carbon atoms in other groups in the formula has no significant effect on activity .
- Control Compound B Control Compound C:
- the compound of the present invention is very safe for rice, and its selection index is much greater than 2. It can effectively control grass weeds such as barnyard grass, crabgrass, foxtail and other broad-leaved weeds, and is an ideal herbicide for rice fields.
- Post-emergence test experiment 3-4 weeks after sowing, the test plants were treated at the 1.5-2 leaf stage and the 4-5 leaf stage of the weeds of the 16 varieties of Longyang direct seeding rice. Cultivate in the greenhouse for 25 days after application. After 25 days, the experimental effects of weeds are counted. For test results, see Table 5-6.
- Longyang 16 is a representative of important long-grain rice varieties in Northeast China. Long-grain rice is sensitive to herbicides, especially HPPD-type mesotrione and bicyclosulone, which are prone to phytotoxicity. Surprisingly, 1-8 (R configuration) is more safe for rice (Longyang 16) and has better activity against the key weed, Qianjin.
- the S body is not safe for rice, that is, the crop is seriously toxic to crops, but it is less active against key weeds, and even inactive at low doses. It is inconsistent with the well-known aryloxyphenoxypropionic acid herbicides and phenoxypropionic acid herbicides. The effective body activity is high, the phytotoxicity is heavy, and the invalid body has almost no activity. The structure-activity relationship is inconsistent.
- 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.
- the compounds of the present invention generally have better weed control effects, especially for weeds such as barnyardgrass, horsetail, foxtail, etc., and velvetleaf, which occur widely in corn fields, rice fields, and wheat fields.
- the main broad-leaved weeds such as radix caulis, needle needle grass, etc. have good effects and have good commercial value.
- the broadleaf weeds that are resistant to ALS inhibitors, such as Chestnut, Sophora vulgare, Shepherd's purse, Maijiagong, Swamp, and Stellaria have extremely high activity.
- the compound of the present invention was treated in the same manner as described above.
- the compounds of the present invention have excellent activity against weeds that are facing a serious challenge in the mechanism of anti-ALS inhibition, and can solve the increasingly serious problem of resistance.
- the present invention also relates to a herbicidal composition containing a herbicidally effective amount of an active ingredient (i) (a compound represented by Formula I) and an active ingredient (ii), and may also include one or more safeners And/or agrochemically acceptable formulation aids, etc.
- the stem and leaf treatment method was used to determine the actual control effect of the mixed weeds in the above parts (i) and (ii), that is, when the weeds were in the 3-4 leaf stage, a manual sprayer with a water content of 30 kg/667m 2 was used Spray the stem and leaves evenly.
- Survey 20 days after treatment, and use Gowing method to calculate the theoretical fresh weight suppression rate (E0 X+YX*Y/100) of each combination of treatments, and then compare it with the measured suppression rate (E) to evaluate the mixed use of the two for weeds
- E-E0 value is greater than 10%, it is synergistic, less than -10% is antagonistic, and between -10% and 10% is additive.
- X is the fresh weight suppression rate when the amount of the active ingredient (i) is P
- Y is the fresh weight suppression rate when the amount of the active ingredient (ii) is Q.
- Table B1 lists specific combinations of other components (i) and components (ii), further illustrating the composition of the present invention.
- the compounds in the column of "component (i)/compound number” are identified in the index table A1.
- the second column of Table B1 lists the specific component (ii) compounds (for example "pyrimsulfuron" in the first row). The remaining rows of Table B1 will be constructed similarly.
- Table B2 has the same structure as Table B1 above, except that the entry below the column heading of "Component (i)/Compound No.” is replaced by the corresponding column entry of "Component (i)/Compound No.” shown below.
- the compounds in the column of "component (i)/compound number” are identified in index tables A1-A152. So, for example, in Table B2, the entries under the column heading "Component (i)/Compound No.” all describe "1-5" (ie, index compounds 1-5 identified in Table A1), and Table B2 The first row below the column heading in the detailed disclosure of a mixture of compounds 1-5 and "pyrisulfuron". Tables B3 to B167 are constructed similarly.
Abstract
The present invention relates to the technical field of pesticides, and specifically relates to an N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or a salt thereof, a preparation method therefor, a herbicidal composition and a use thereof. The structural formula of the compound is shown in formula I. X denotes O, S, SO, SO 2 or NR 1; Y denotes halogen, cyano, cyanoalkyl, carboxyl, nitro or etc.; or -X-Y denotes unsubstituted or substituted five-membered or six-membered heterocyclyl or heteroaryl; Z denotes hydrogen, halogen, cyano, OR 4, -alkyl-OR 4, -O-alkyl-N(R 5) 2 or etc.; M denotes hydrogen, OR 6, SR 6, COR 6, COOR 6, CON(R 7) 2 or etc. The compound is low in use amount and excellent in herbicidal activity, has higher crop safety, and establishes good selectivity especially for important crops like paddy and etc.
Description
本发明属于农药技术领域，具体涉及一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类或其盐、制备方法、除草组合物和应用。The invention belongs to the technical field of pesticides, and specifically relates to an N-(1,3,4-oxadiazol-2-yl)aryl formamide or a salt thereof, a preparation method, a herbicidal composition and applications.
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，例如，WO2014086746A1、WO2016146561A1、WO2014086734A1、WO2013017559A1、WO2017144402A1、WO2012126932A1、WO2012028579A1等公开了某些芳基甲酰胺类化合物及其作为除草剂的用途。但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，尤其是随着ALS抑制机理的五氟磺草胺、双草醚、嘧啶肟草醚、烟嘧磺隆，ACCe类抑制机理的氰氟草酯、烯草酮、精喹禾灵、恶唑酰草胺等以及草甘膦等市场主流杂草除草剂抗性的严重发生，小麦、玉米、水稻、棉花、大豆等作物遇到严峻挑战，缺乏有效防除抗性杂草的药剂，这就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。The control of weeds is a crucial link in the process of achieving efficient agriculture, although there are many types of herbicides on the market, for example, WO2014086746A1, WO2016146561A1, WO2014086734A1, WO2013017559A1, WO2017144402A1, WO2012126932A1, WO2012028579A1, etc. disclose some aryl formamides Compounds and their use as herbicides. However, due to the continuous expansion of the market, the resistance of weeds, the service life of drugs and the economics of drugs, and people's increasing attention to the environment, especially with the mechanism of ALS inhibition pentasulam, diquat, Pyridoxime oxachlor, nicosulfuron, ACCe-based inhibitory mechanisms of cyflufenazone, clethodim, quinoxachlor, oxaflufen, etc. as well as glyphosate and other market mainstream weed herbicides are seriously resistant Occurred, wheat, corn, rice, cotton, soybean and other crops encountered severe challenges, lacking effective agents to control resistant weeds, which requires scientists to continue to research and develop new efficient, safe, economic, and different modes of action Varieties of herbicides.
另外，市场上有很多手性的除草剂被开发出来，比如芳氧苯氧丙酸类除草剂精喹禾灵、精吡氟禾草灵、氰氟草酯、恶唑酰草胺、精恶唑禾草灵；芳氧丙酸类除草剂2甲4氯丙酸、2,4-滴丙酸；氯代酰胺类除草剂S异丙甲草胺，这些手性除草剂的开发大幅降低了无效体的使用，对环境安全提供了更高的保障，但从未有含硫的手性除草剂被商业化，而本申请还惊奇地发现了芳基甲酰胺类化合物的硫手性除草剂，具有巨大的商业化价值。In addition, many chiral herbicides have been developed on the market, such as aryloxyphenoxypropionic acid herbicides quizalofop, pirfenachlor, cyflufenazone, oxaflufen, and oxacox Carbendazim; aryloxypropionic acid herbicides 2 methyl 4-chloropropionic acid, 2,4-D propionic acid; chloroamide herbicide S metolachlor, the development of these chiral herbicides has greatly reduced The use of invalid bodies provides a higher guarantee for environmental safety, but there has never been commercialization of sulfur-containing chiral herbicides, and this application has surprisingly discovered sulfur-chiral herbicides of aryl formamide compounds , With huge commercial value.
发明内容Summary of the invention
本发明提供了一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类或其盐、制备方法、除草组合物和应用，所述化合物的用量低，除草活性优异，且具有更高的作物安全性，尤其是对于水稻等关键农作物建立了良好的选择性。The invention provides an N-(1,3,4-oxadiazol-2-yl)aryl formamide or its salt, a preparation method, a herbicidal composition and an application, the amount of the compound is low, and the herbicidal activity Excellent, and with higher crop safety, especially for rice and other key crops to establish a good selectivity.
本发明采用的技术方案如下：The technical scheme adopted by the present invention is as follows:
一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其结构式如下：An N-(1,3,4-oxadiazol-2-yl) aryl formamide compound or its salt, the structural formula is as follows:
其中，X代表O、S、SO、SO
2或NR
1；
Among them, X represents O, S, SO, SO 2 or NR 1 ;
Y代表卤素，氰基，氰基烷基，羧基，硝基，N(R
2)
2，-烷基-N(R
2)
2，CON(R
2)
2，-烷基-CON(R
2)
2，-烷基-N(R
2)
3
+I
-，羟基烷基，被氨基和羧基取代的烷基，OR
3，SR
3，-烷基-SOR
3，-烷基-OR
3，-烷基-SR
3，COR
3，COOR
3，-烷基-COR
4，-烷基-COOR
4，-烷基-OCOR
3，Si(R
3)
3，-烷基-O-Si(R
3)
3，-烷基-O-N＝C(R
3)
2，烷基，卤代烷基，未取代或被选自卤素、氰基、环烷基、烷基羰基、烷氧基羰基、烷氧基、烷硫基、烷基亚硫酰基、烷基磺酰基、三烷基硅基中的至少一个基团所取代的烯基、炔基，未取代或取代的环烷基、环烷基烷基，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；
Y represents halogen, cyano, cyanoalkyl, carboxyl, nitro, N(R 2 ) 2 , -alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , -alkyl-CON(R 2 ) 2, - alkyl -N (R 2) 3 + I -, hydroxyalkyl, amino and carboxy substituted alkyl, OR 3, SR 3, - alkyl -SOR 3, - alkyl -OR 3, -Alkyl-SR 3 , COR 3 , COOR 3 , -alkyl-COR 4 , -alkyl-COOR 4 , -alkyl-OCOR 3 , Si(R 3 ) 3 , -alkyl-O-Si(R 3 ) 3 ,-alkyl-ON=C(R 3 ) 2 , alkyl, haloalkyl, unsubstituted or selected from halogen, cyano, cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxy , Alkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl substituted alkenyl, alkynyl, unsubstituted or substituted cycloalkyl, cycloalkylalkyl , Unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl;
或者-X-Y代表未取代或取代的五元或六元杂环基或杂芳基，该环上除含有C原子和1-位上的N原子外，还含有0-3个以下原子或基团作为环的组成部分：O、N、NR
1、SO
2、C＝O；
Or -XY represents an unsubstituted or substituted five-membered or six-membered heterocyclic group or heteroaryl group, in addition to the C atom and the N atom at the 1-position, the ring also contains 0 to 3 atoms or groups below As a component of the ring: O, N, NR 1 , SO 2 , C=O;
Z代表氢，卤素，氰基，OR
4，-烷基-OR
4，-O-烷基-N(R
5)
2，-烷基-O-烷基-N(R
5)
2，N(R
5)
2，-烷基-(C＝O)
m-N(R
5)
2，-NH-烷基-N(R
5)
2，不含或含有卤素的烷基、烯基、炔基、烷氧基羰基、烷氧基羰基烷基、烷基羰基、烷基羰基烷基、烷基羰基氧基烷基、烷硫基、烷基亚磺酰基、烷基磺酰基，未取代或取代的环烷基，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、杂环基羰基烷基、芳基羰基烷基、杂芳基羰基烷基、杂环基羰基氧基烷基、芳基羰基氧基烷基、杂芳基羰基氧基烷基；
Z represents hydrogen, halogen, cyano, OR 4 , -alkyl-OR 4 , -O-alkyl-N(R 5 ) 2 , -alkyl-O-alkyl-N(R 5 ) 2 , N( R 5 ) 2 ,-alkyl-(C═O) m -N(R 5 ) 2 ,-NH-alkyl-N(R 5 ) 2 , alkyl, alkenyl, alkynyl groups that do not contain or contain halogen , Alkoxycarbonyl, alkoxycarbonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, unsubstituted or substituted Cycloalkyl, unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, heterocyclylcarbonylalkyl, arylcarbonylalkyl , Heteroarylcarbonylalkyl, heterocyclylcarbonyloxyalkyl, arylcarbonyloxyalkyl, heteroarylcarbonyloxyalkyl;
M代表氢，OR
6，SR
6，COR
6，COOR
6，OCOR
6，CON(R
7)
2，N(R
7)
2，NR
8COOR
6，NR
8CON(R
7)
2，-烷基-R，不含或含有卤素的烷基、烯基、炔基、环烷基，以及未取代或取代的芳基烷基、杂芳基烷基；
M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -alkyl -R, alkyl group, alkenyl group, alkynyl group, cycloalkyl group not containing or containing halogen, and unsubstituted or substituted arylalkyl group, heteroarylalkyl group;
R代表不含或含有卤素的烯基、炔基、环烷基，CN，OR
11，OCOR
11，COOR
11，COR
11，-O-(C＝O)-O-R
11，OSO
2R
12，SO
2OR
11，-S(O)
nR
12，N(R
13)
2，CON(R
13)
2，SO
2N(R
13)
2，NR
14COR
11，NR
14SO
2R
12，-O-(C＝O)-N(R
13)
2；
R represents alkenyl, alkynyl, cycloalkyl without or containing halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)-OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O -(C＝O)-N(R 13 ) 2 ;
R
4、R
6、R
11分别独立地代表氢、不含或含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、烷氧基烷基，以及未取代或取代的杂环基、杂环基烷基、杂环基氧基烷基、芳基、芳基烷基、芳基氧基烷基、杂芳基、杂芳基烷基、杂芳基氧基烷基；
R 4 , R 6 , and R 11 independently represent hydrogen, an alkyl group containing no or halogen, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, alkoxyalkyl group, and Unsubstituted or substituted heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl, heteroaryl Oxyalkyl;
R
3、R
12分别独立地代表不含或含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、烷氧基烷基，以及未取代或取代的杂环基、杂环基烷基、芳基、芳基烷基、杂芳基、杂芳基烷基；
R 3 and R 12 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, alkoxyalkyl, and unsubstituted or substituted Heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl;
R
1、R
2、R
5、R
7、R
8、R
13、R
14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R
21)
2、CON(R
21)
2、OR
21、COR
21、CO
2R
21、COSR
21、OCOR
21、S(O)
rR
22、烷基、卤代烷基、烯基、卤代烯基、炔基、卤代炔基、环烷基、环烯基、卤代环烷基、烷氧基烷基、环烷基烷基、芳基、芳基烷基、芳基氧基、芳基氧基烷基、芳基烷基氧基、 芳基羰基、芳基磺酰基、杂芳基、杂芳基烷基、杂芳基氧基、杂芳基氧基烷基、杂芳基烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基烷基、杂环基氧基、杂环基氧基烷基、杂环基烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR
21-烷基、杂芳基-NR
21-烷基、杂环基-NR
21-烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR
21、S(O)
rR
22、N(R
21)
2、NR
21OR
21、COR
21、OCOR
21、SCOR
22、NR
21COR
21、NR
21SO
2R
22、CO
2R
21、COSR
21、CON(R
21)
2和烷氧基烷氧基羰基；
R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , alkyl, haloalkyl, alkenyl, haloalkenyl , Alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryl Oxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyl Oxygen, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclyloxyalkyl, heterocyclylalkyloxy, heterocyclylcarbonyl , Heterocyclylsulfonyl, aryl-NR 21 -alkyl, heteroaryl-NR 21 -alkyl, heterocyclyl-NR 21 -alkyl, wherein the last 35 groups mentioned are each 0, 1 , 2 or 3 group substitutions selected from cyano, halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and alkoxyalkoxycarbonyl;
R
21分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基；
R 21 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;
R
22分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基；
R 22 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;
m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;
当X代表S、SO时，Y不为甲基。When X represents S and SO, Y is not methyl.
优选地，X代表O、S、SO、SO
2或NR
1；
Preferably, X represents O, S, SO, SO 2 or NR 1 ;
Y代表卤素，氰基，氰基C1-C8烷基，羧基，硝基，N(R
2)
2，-(C1-C8)烷基-N(R
2)
2，CON(R
2)
2，-(C1-C8)烷基-CON(R
2)
2，-(C1-C8)烷基-N(R
2)
3
+I
-，羟基C1-C8烷基，被氨基和羧基取代的C1-C8烷基，OR
3，SR
3，-(C1-C8)烷基-SOR
3，-(C1-C8)烷基-OR
3，-(C1-C8)烷基-SR
3，COR
3，COOR
3，-(C1-C8)烷基-COR
4，-(C1-C8)烷基-COOR
4，-(C1-C8)烷基-OCOR
3，Si(R
3)
3，-(C1-C8)烷基-O-Si(R
3)
3，-(C1-C8)烷基-O-N＝C(R
3)
2，C1-C8烷基，卤代C1-C8烷基，未取代或被选自卤素、氰基、C3-C8环烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷氧基、C1-C8烷硫基、C1-C8烷基亚硫酰基、C1-C8烷基磺酰基、三C1-C8烷基硅基中的至少一个基团所取代的C2-C8烯基、C2-C8炔基，未取代或被选自C1-C8烷基、卤素、苯基中的至少一个基团取代的C3-C8环烷基、C3-C8环烷基C1-C8烷基，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；
Y represents halogen, cyano, cyano C1-C8 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C8)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C8) alkyl -CON (R 2) 2, - (C1-C8) alkyl -N (R 2) 3 + I -, hydroxy C1-C8 alkyl, substituted amino and carboxyl C1- C8 alkyl, OR 3 , SR 3 , -(C1-C8)alkyl-SOR 3 , -(C1-C8)alkyl-OR 3 , -(C1-C8)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C8)alkyl-COR 4 ,-(C1-C8)alkyl-COOR 4 ,-(C1-C8)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C8 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C8)alkyl-ON=C(R 3 ) 2 ,C1-C8 alkyl, halogenated C1-C8 alkyl, unsubstituted or selected From halogen, cyano, C3-C8 cycloalkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylsulfinyl , C1-C8 alkylsulfonyl, C2-C8 alkenyl, C2-C8 alkynyl substituted with at least one group of tri-C1-C8 alkylsilyl, unsubstituted or selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl substituted with at least one group of halogen, phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl;
或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，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、苯氧基，以及含有或不含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基、烷硫基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基、烷基亚硫酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基酰氧基中的至少一个基团所取代的
Or -XY represents unsubstituted or selected by halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or substituted by at least one group selected from halogen, alkyl, alkoxy Substituted phenyl, benzyl, phenoxy, and alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkoxyalkyl with or without halogen Substituted by at least one group of alkyl, alkylthioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylacyloxy of
Z代表氢，卤素，氰基，OR
4，-(C1-C8)烷基-OR
4，-O-(C1-C8)烷基-N(R
5)
2，-(C1-C8)烷基-O-(C1-C8)烷基-N(R
5)
2，N(R
5)
2，-(C1-C8)烷基-(C＝O)
m-N(R
5)
2，-NH-(C1-C8)烷基-N(R
5)
2，不含或含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C1-C8烷氧基羰基、C1-C8烷氧基羰基C1-C8烷基、C1-C8烷基羰基、C1-C8烷基羰基C1-C8烷基、C1-C8烷基羰基氧基C1-C8烷基、C1-C8烷硫基、C1-C8烷基亚磺酰基、C1-C8烷基磺酰基，未取代或被选自C1-C8烷基、卤素、苯基中的至少一个基团取代的C3-C8环烷基，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、杂环基羰基C1-C8烷基、芳基羰基C1-C8烷基、杂芳基羰基C1-C8烷基、杂环基羰基氧基C1-C8烷基、芳基羰基氧基C1-C8烷基、杂芳基羰基氧基C1-C8烷基；
Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C8)alkyl-OR 4 , -O-(C1-C8)alkyl-N(R 5 ) 2 , -(C1-C8)alkyl -O-(C1-C8)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C8)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C8)alkyl-N(R 5 ) 2 , C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxycarbonyl, C1- C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy C1-C8 alkyl, C1-C8 alkylthio , C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C8 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl, heterocyclylcarbonyl C1-C8 alkyl , Arylcarbonyl C1-C8 alkyl, heteroarylcarbonyl C1-C8 alkyl, heterocyclic carbonyloxy C1-C8 alkyl, arylcarbonyloxy C1-C8 alkyl, heteroarylcarbonyloxy C1 -C8 alkyl;
M代表氢，OR
6，SR
6，COR
6，COOR
6，OCOR
6，CON(R
7)
2，N(R
7)
2，NR
8COOR
6，NR
8CON(R
7)
2，-(C1-C8烷基)-R，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，以及未取代或取代的芳基C1-C8烷基、杂芳基C1-C8烷基；
M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C8 alkyl)-R, C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and unsubstituted or substituted aryl C1-C8 Alkyl, heteroaryl C1-C8 alkyl;
R代表不含或含有卤素的C2-C8烯基、C2-C8炔基、C3-C8环烷基，CN，OR
11，OCOR
11，COOR
11，COR
11，-O-(C＝O)-O-R
11，OSO
2R
12，SO
2OR
11，-S(O)
nR
12，N(R
13)
2，CON(R
13)
2，SO
2N(R
13)
2，NR
14COR
11，NR
14SO
2R
12，-O-(C＝O)-N(R
13)
2；
R represents C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl without or containing halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;
R
4、R
6、R
11分别独立地代表氢、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、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C1-C8烷氧基C1-C8烷基，以及未取代或取代的杂环基、杂环基C1-C8烷基、杂环基氧基C1-C8烷基、芳基、芳基C1-C8烷基、芳基氧基C1-C8烷基、杂芳基、杂芳基C1-C8烷基、杂芳基氧基C1-C8烷基；
R 4 , R 6 , and R 11 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkane C1-C8 alkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy C1-C8 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C8 alkyl, heterocyclyloxy C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryloxy C1-C8 alkyl, heteroaryl, heteroaryl C1-C8 alkyl, heteroaryloxy C1-C8 alkyl ;
R
3、R
12分别独立地代表不含或含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C1-C8烷氧基C1-C8烷基，以及未取代或取代的杂环基、杂环基C1-C8烷基、芳基、芳基C1-C8烷基、杂芳基、杂芳基C1-C8烷基；
R 3 and R 12 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, C3-C8 cycloalkenyl group, C1-C8 alkoxy C1-C8 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C8 alkyl group, aryl group, aryl C1-C8 alkyl group , Heteroaryl, heteroaryl C1-C8 alkyl;
R
1、R
2、R
5、R
7、R
8、R
13、R
14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R
21)
2、CON(R
21)
2、OR
21、COR
21、CO
2R
21、COSR
21、OCOR
21、S(O)
rR
22、C1-C8烷基、卤代C1-C8烷基、C2-C8烯基、卤代C2-C8烯基、C2-C8炔基、卤代C2-C8炔基、C3-C8环烷基、C3-C8环烯基、卤代C3-C8环烷基、C1-C8烷氧基C1-C8烷基、C3-C8环烷基C1-C8烷基、芳基、芳基C1-C8烷基、芳基氧基、芳基氧基C1-C8烷基、芳基C1-C8烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C8烷基、杂芳基氧基、杂芳基氧基C1-C8烷基、杂芳基C1-C8烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C8烷基、杂环基氧基、杂环基氧基C1-C8烷基、杂环基C1-C8烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR
21-(C1-C8)烷基、杂芳基-NR
21-(C1-C8)烷基、杂环基-NR
21-(C1-C8)烷 基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR
21、S(O)
rR
22、N(R
21)
2、NR
21OR
21、COR
21、OCOR
21、SCOR
22、NR
21COR
21、NR
21SO
2R
22、CO
2R
21、COSR
21、CON(R
21)
2和C1-C8烷氧基C1-C8烷氧基羰基；
R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C8 alkyl, halogenated C1-C8 alkyl , C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, halogenated C3-C8 cycloalkane Group, C1-C8 alkoxy C1-C8 alkyl, C3-C8 cycloalkyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryloxy, aryloxy C1-C8 alkyl Group, aryl C1-C8 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C8 alkyl, heteroaryloxy, heteroaryloxy C1-C8 alkyl , Heteroaryl C1-C8 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C8 alkyl, heterocyclyloxy, heterocyclyloxy C1-C8 Alkyl, heterocyclyl C1-C8 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C8)alkyl, heteroaryl-NR 21 -(C1-C8 )Alkyl, heterocyclyl-NR 21 -(C1-C8)alkyl, wherein the last-mentioned 35 groups are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C8 alkoxy C1-C8 alkoxycarbonyl;
R
21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；
R 21 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;
R
22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；
R 22 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;
m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;
其中，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，“杂芳基”是指
Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers to
其中，其任选地可被选自卤素，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、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”，被选自氢、烷基、烯基、炔基、环烷基、环烷基烷基、COR”、SO
2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基，以及-OCH
2CH
2-，-OCH
2O-，-OCH
2CH
2O-中的至少一个基团所取代；
Wherein, it may optionally be selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxy, mercapto, formyl, unsubstituted or selected from at least one group selected from halogen, alkyl, alkoxy Phenyl, benzyl, phenoxy substituted by groups, with or without halogen alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, OR", SR", -alkyl-OR ", -alkyl-SR", COR", COOR", COSR", SOR", SO 2 R", OCOR", SCOR" are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, Amino or aminocarbonyl substituted by one or two groups of cycloalkylalkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by at least one group;
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'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”分别独立地代表氢，含有或不含有卤素的烷基、烯基、炔基、环烷基或环烷基烷基。R" independently represents hydrogen, alkyl or alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl with or without halogen.
更优选地，X代表O、S、SO、SO
2或NR
1；
More preferably, X represents O, S, SO, SO 2 or NR 1 ;
Y代表卤素，氰基，氰基C1-C6烷基，羧基，硝基，N(R
2)
2，-(C1-C6)烷基-N(R
2)
2，CON(R
2)
2，-(C1-C6)烷基-CON(R
2)
2，-(C1-C6)烷基-N(R
2)
3
+I
-，羟基C1-C6烷基，被氨基和羧基取代的C1-C6烷基，OR
3，SR
3，-(C1-C6)烷基-SOR
3，-(C1-C6)烷基-OR
3，-(C1-C6)烷基-SR
3，COR
3，COOR
3，-(C1-C6)烷基-COR
4，-(C1-C6)烷基-COOR
4，-(C1-C6)烷基-OCOR
3，Si(R
3)
3，-(C1-C6)烷基-O-Si(R
3)
3，-(C1-C6)烷基-O-N＝C(R
3)
2，C1-C6烷基，卤代C1-C6烷基，未取代或被选自卤素、氰基、C3-C6环烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、三C1-C6烷基硅基中的至少一个基团所取代的C2-C6烯基、C2-C6炔基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基、C3-C6环烷基C1-C6烷基，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；
Y represents halogen, cyano, cyano C1-C6 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C6)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C6) alkyl -CON (R 2) 2, - (C1-C6) alkyl -N (R 2) 3 + I -, hydroxy C1-C6 alkyl, substituted amino and carboxyl C1- C6 alkyl, OR 3 , SR 3 , -(C1-C6)alkyl-SOR 3 , -(C1-C6)alkyl-OR 3 , -(C1-C6)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C6)alkyl-COR 4 ,-(C1-C6)alkyl-COOR 4 ,-(C1-C6)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C6 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C6)alkyl-ON=C(R 3 ) 2 ,C1-C6 alkyl, halogenated C1-C6 alkyl, unsubstituted or selected From halogen, cyano, C3-C6 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl , C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl substituted by at least one group of tri-C1-C6 alkylsilyl, unsubstituted or selected from C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl substituted with at least one group of halogen and phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl;
或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，巯基，甲酰基，未取代或被选自卤素、C1-C8烷基、C1-C8烷氧基中的1、2或3个基团所取代的苯基、苄基、苯氧基，以及含有或不含有卤素的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、C1-C8烷硫基、C1-C8烷氧基C1-C8烷基、C1-C8烷硫基C1-C8烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷基亚硫酰基、C1-C8烷基磺酰基、C1-C8烷基氨基、二C1-C8烷基氨基、C1-C8烷基酰氧基中的1、2或3个基团所取代的
Or -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 with or without halogen Cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1- C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, di-C1-C8 alkylamino , C1-C8 alkylacyloxy substituted by 1, 2 or 3 groups
Z代表氢，卤素，氰基，OR
4，-(C1-C6)烷基-OR
4，-O-(C1-C6)烷基-N(R
5)
2，-(C1-C6)烷基-O-(C1-C6)烷基-N(R
5)
2，N(R
5)
2，-(C1-C6)烷基-(C＝O)
m-N(R
5)
2，-NH-(C1-C6)烷基-N(R
5)
2，不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C6烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷基羰基氧基C1-C6烷基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基，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、杂环基羰基C1-C6烷基、 芳基羰基C1-C6烷基、杂芳基羰基C1-C6烷基、杂环基羰基氧基C1-C6烷基、芳基羰基氧基C1-C6烷基、杂芳基羰基氧基C1-C6烷基；
Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C6)alkyl-OR 4 , -O-(C1-C6)alkyl-N(R 5 ) 2 ,-(C1-C6)alkyl -O-(C1-C6)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C6)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C6)alkyl-N(R 5 ) 2 , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxycarbonyl, C1- C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy C1-C6 alkyl, C1-C6 alkylthio , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl, heterocyclylcarbonyl C1-C6 alkyl , Arylcarbonyl C1-C6 alkyl, heteroarylcarbonyl C1-C6 alkyl, heterocyclic carbonyloxy C1-C6 alkyl, arylcarbonyloxy C1-C6 alkyl, heteroarylcarbonyloxy C1 -C6 alkyl;
M代表氢，OR
6，SR
6，COR
6，COOR
6，OCOR
6，CON(R
7)
2，N(R
7)
2，NR
8COOR
6，NR
8CON(R
7)
2，-(C1-C6烷基)-R，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，以及未取代或取代的芳基C1-C6烷基、杂芳基C1-C6烷基；
M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C6 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C1-C6 unsubstituted or substituted aryl Alkyl, heteroaryl C1-C6 alkyl;
R代表不含或含有卤素的C2-C6烯基、C2-C6炔基、C3-C6环烷基，CN，OR
11，OCOR
11，COOR
11，COR
11，-O-(C＝O)-O-R
11，OSO
2R
12，SO
2OR
11，-S(O)
nR
12，N(R
13)
2，CON(R
13)
2，SO
2N(R
13)
2，NR
14COR
11，NR
14SO
2R
12，-O-(C＝O)-N(R
13)
2；
R represents C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl without or with halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;
R
4、R
6、R
11分别独立地代表氢、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、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C1-C6烷氧基C1-C6烷基，以及未取代或取代的杂环基、杂环基C1-C6烷基、杂环基氧基C1-C6烷基、芳基、芳基C1-C6烷基、芳基氧基C1-C6烷基、杂芳基、杂芳基C1-C6烷基、杂芳基氧基C1-C6烷基；
R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C6 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C6 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C6 alkyl, heterocyclyloxy C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy C1-C6 alkyl ;
R
3、R
12分别独立地代表不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C1-C6烷氧基C1-C6烷基，以及未取代或取代的杂环基、杂环基C1-C6烷基、芳基、芳基C1-C6烷基、杂芳基、杂芳基C1-C6烷基；
R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C6 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C6 alkyl group, aryl group, aryl C1-C6 alkyl group , Heteroaryl, heteroaryl C1-C6 alkyl;
R
1、R
2、R
5、R
7、R
8、R
13、R
14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R
21)
2、CON(R
21)
2、OR
21、COR
21、CO
2R
21、COSR
21、OCOR
21、S(O)
rR
22、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、C3-C6环烯基、卤代C3-C6环烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基C1-C6烷基、芳基、芳基C1-C6烷基、芳基氧基、芳基氧基C1-C6烷基、芳基C1-C6烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C6烷基、杂芳基氧基、杂芳基氧基C1-C6烷基、杂芳基C1-C6烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C6烷基、杂环基氧基、杂环基氧基C1-C6烷基、杂环基C1-C6烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR
21-(C1-C6)烷基、杂芳基-NR
21-(C1-C6)烷基、杂环基-NR
21-(C1-C6)烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR
21、S(O)
rR
22、N(R
21)
2、NR
21OR
21、COR
21、OCOR
21、SCOR
22、NR
21COR
21、NR
21SO
2R
22、CO
2R
21、COSR
21、CON(R
21)
2和C1-C6烷氧基C1-C6烷氧基羰基；
R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkane Group, C1-C6 alkoxy C1-C6 alkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy, aryloxy C1-C6 alkyl Group, aryl C1-C6 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy, heteroaryloxy C1-C6 alkyl , Heteroaryl C1-C6 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C6 alkyl, heterocyclyloxy, heterocyclyloxy C1-C6 Alkyl, heterocyclyl C1-C6 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C6)alkyl, heteroaryl-NR 21 -(C1-C6 )Alkyl, heterocyclyl-NR 21 -(C1-C6)alkyl, wherein the last-mentioned 35 groups are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C6 alkoxy C1-C6 alkoxycarbonyl;
R
21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；
R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;
R
22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；
R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;
m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;
其中，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，“杂芳基”是指
Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers to
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-C8烷基、C1-C8烷氧基中的1、2或3个基团所取代的苯基、苄基、苯氧基，含有或不含有卤素的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、OR”、SR”、-(C1-C8)烷基-OR”、-(C1-C8)烷基-SR”、COR”、COOR”、COSR”、SOR”、SO
2R”、OCOR”、SCOR”，被选自氢、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、COR”、SO
2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基，以及-OCH
2CH
2-，-OCH
2O-，-OCH
2CH
2O-中的0、1、2或3个基团所取代；
Among them, it is selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl , C3-C8 cycloalkyl C1-C8 alkyl, OR", SR", -(C1-C8)alkyl-OR", -(C1-C8)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 ring Amino or aminocarbonyl substituted with one or two groups of alkyl C1-C8 alkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by 0, 1, 2 or 3 groups;
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-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、C3-C8环烷基C1-C8烷基、C1-C8烷氧基、C2-C8烯基氧基、C2-C8炔基氧基、C3-C8环烷基氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基羰基、C1-C8烷基磺酰基、C1-C8烷基磺酰基C1-C8烷基、C1-C8烷基羰基、C1-C8烷基羰基C1-C8烷基、C1-C8烷基酰氧基、C1-C8烷基氨基、C1-C8烷基氨基羰基、C1-C8烷氧基氨基羰基、C1-C8烷氧基羰基C1-C8烷基、C1-C8烷氨基羰基C1-C8烷基、三C1-C8烷基甲硅烷基、二C1-C8烷基膦酰基；R'independently represents hydrogen, nitro, hydroxy, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, with or without fluorine, chlorine, or bromine C3-C8 cycloalkenyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy , C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthiocarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylsulfonyl C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkylacyloxy, C1-C8 alkylamino, C1-C8 alkylaminocarbonyl, C1-C8 alkoxyamino Carbonyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylaminocarbonyl C1-C8 alkyl, tri-C1-C8 alkylsilyl, di-C1-C8 alkylphosphono;
R”分别独立地代表氢，含有或不含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基或C3-C8环烷基C1-C8烷基。R” independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl with or without halogen .
进一步优选地，X代表O、S、SO、SO
2或NR
1；
Further preferably, X represents O, S, SO, SO 2 or NR 1 ;
Y代表卤素，氰基，氰基C1-C2烷基，羧基，硝基，N(R
2)
2，-(C1-C2)烷基-N(R
2)
2，CON(R
2)
2，-(C1-C2)烷基-CON(R
2)
2，-(C1-C2)烷基-N(R
2)
3
+I
-，羟基C1-C2烷基，被氨基和羧基取代的C1-C2烷基，OR
3，SR
3，-(C1-C2)烷基-SOR
3，-(C1-C2)烷基-OR
3，-(C1-C2)烷基-SR
3，COR
3，COOR
3，-(C1-C2)烷基-COR
4，-(C1-C2)烷基-COOR
4，-(C1-C2)烷基-OCOR
3，Si(R
3)
3，-(C1-C2)烷基-O-Si(R
3)
3，-(C1-C2)烷基-O-N＝C(R
3)
2，C1-C6烷基，卤代C1-C6烷基，未取代或被选自卤素、氰基、C3-C6环烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、三C1-C6烷基硅基中的至少一个基团所取代的C2-C6烯基、C2-C6炔基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基、C3-C6环烷基C1-C2烷基，未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C2烷基、芳基C1-C2烷基、杂芳基C1-C2烷基；
Y represents halogen, cyano, cyano C1-C2 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C2)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C2) alkyl -CON (R 2) 2, - (C1-C2) alkyl -N (R 2) 3 + I -, hydroxy C1-C2 alkyl, substituted amino and carboxyl C1- C2 alkyl, OR 3 , SR 3 , -(C1-C2)alkyl-SOR 3 , -(C1-C2)alkyl-OR 3 , -(C1-C2)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C2)alkyl-COR 4 ,-(C1-C2)alkyl-COOR 4 ,-(C1-C2)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C2 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C2)alkyl-ON=C(R 3 ) 2 ,C1-C6 alkyl, halogenated C1-C6 alkyl, unsubstituted or selected From halogen, cyano, C3-C6 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl , C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl substituted by at least one group of tri-C1-C6 alkylsilyl, unsubstituted or selected from C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl substituted with at least one group of halogen, phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C2 alkyl, aryl C1-C2 alkyl, heteroaryl C1-C2 alkyl;
或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，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1、2或3个基团所取代的苯基、苄基、苯氧基，以及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-C2烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氧基C1-C2烷基、C1-C6烷硫基C1-C2烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6烷基氨基、二C1-C6烷基氨基、C1-C6烷基酰氧基中的1、2或3个基团所取代的
Or -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxyl, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 with or without halogen Cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkylthio C1- C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, di-C1-C6 alkylamino , Substituted by 1, 2 or 3 groups in C1-C6 alkylacyloxy
Z代表氢，卤素，氰基，OR
4，-(C1-C2)烷基-OR
4，-O-(C1-C2)烷基-N(R
5)
2，-(C1-C2)烷基-O-(C1-C2)烷基-N(R
5)
2，N(R
5)
2，-(C1-C2)烷基-(C＝O)
m-N(R
5)
2，-NH-(C1-C2)烷基-N(R
5)
2，不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C2烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C2烷基、C1-C6烷基羰基氧基C1-C2烷基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基，未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C2烷基、芳基C1-C2烷基、杂芳基C1-C2烷基、杂环基羰基C1-C2烷基、芳基羰基C1-C2烷基、杂芳基羰基C1-C2烷基、杂环基羰基氧基C1-C2烷基、芳基羰基氧基C1-C2烷基、杂芳基羰基氧基C1-C2烷基；
Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C2)alkyl-OR 4 , -O-(C1-C2)alkyl-N(R 5 ) 2 , -(C1-C2)alkyl -O-(C1-C2)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C2)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C2)alkyl-N(R 5 ) 2 , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxycarbonyl, C1- C6 alkoxycarbonyl C1-C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C2 alkyl, C1-C6 alkylcarbonyloxy C1-C2 alkyl, C1-C6 alkylthio , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C2 alkyl, aryl C1-C2 alkyl, heteroaryl C1-C2 alkyl, heterocyclylcarbonyl C1-C2 alkyl , Arylcarbonyl C1-C2 alkyl, heteroarylcarbonyl C1-C2 alkyl, heterocyclic carbonyloxy C1-C2 alkyl, arylcarbonyloxy C1-C2 alkyl, heteroarylcarbonyloxy C1 -C2 alkyl;
M代表氢，OR
6，SR
6，COR
6，COOR
6，OCOR
6，CON(R
7)
2，N(R
7)
2，NR
8COOR
6，NR
8CON(R
7)
2，-(C1-C2烷基)-R，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，以及未取代或取代的芳基C1-C2烷基、杂芳基C1-C2烷基；
M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C2 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and unsubstituted or substituted aryl C1-C2 Alkyl, heteroaryl C1-C2 alkyl;
R代表不含或含有卤素的C2-C6烯基、C2-C6炔基、C3-C6环烷基，CN，OR
11，OCOR
11，COOR
11，COR
11，-O-(C＝O)-O-R
11，OSO
2R
12，SO
2OR
11，-S(O)
nR
12，N(R
13)
2，CON(R
13)
2，SO
2N(R
13)
2，NR
14COR
11，NR
14SO
2R
12，-O-(C＝O)-N(R
13)
2；
R represents C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl without or with halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;
R
4、R
6、R
11分别独立地代表氢、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、C3-C6环烷基C1-C2烷基、C3-C6环烯基、C1-C6烷氧基C1-C2烷基，以及未取代或取代的杂环基、杂环基C1-C2烷基、杂环基氧基C1-C2烷基、芳基、芳基C1-C2烷基、芳基氧基C1-C2烷基、杂芳基、杂芳基C1-C2烷基、杂芳基氧基C1-C2烷基；
R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C2 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C2 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C2 alkyl, heterocyclyloxy C1-C2 alkyl, aryl, aryl C1-C2 alkyl, aryloxy C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryloxy C1-C2 alkyl ;
R
3、R
12分别独立地代表不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C2烷基、C3-C6环烯基、C1-C6烷氧基C1-C2烷基，以及未取代或取代的杂环基、杂环基C1-C2烷基、芳基、芳基C1-C2烷基、杂芳基、杂芳基C1-C2烷基；
R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C2 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C2 alkyl group, aryl group, aryl C1-C2 alkyl group , Heteroaryl, heteroaryl C1-C2 alkyl;
R
1、R
2、R
5、R
7、R
8、R
13、R
14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R
21)
2、CON(R
21)
2、OR
21、COR
21、CO
2R
21、COSR
21、OCOR
21、S(O)
rR
22、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、C3-C6环烯基、卤代C3-C6环烷基、C1-C6烷氧基C1-C2烷基、C3-C6环烷基C1-C2烷基、芳基、芳基C1-C2烷基、芳基氧基、芳基氧基C1-C2烷基、芳基C1-C2烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C2烷基、杂芳基氧基、杂芳基氧基C1-C2烷基、杂芳基C1-C2烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C2烷基、杂环基氧基、杂环基氧基C1-C2烷基、杂环基C1-C2烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR
21-(C1-C2)烷基、杂芳基-NR
21-(C1-C2)烷基、杂环基-NR
21-(C1-C2)烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR
21、S(O)
rR
22、N(R
21)
2、NR
21OR
21、COR
21、OCOR
21、SCOR
22、NR
21COR
21、NR
21SO
2R
22、CO
2R
21、COSR
21、CON(R
21)
2和C1-C6烷氧基C1-C2烷氧基羰基；
R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkane Group, C1-C6 alkoxy C1-C2 alkyl, C3-C6 cycloalkyl C1-C2 alkyl, aryl, aryl C1-C2 alkyl, aryloxy, aryloxy C1-C2 alkyl Group, aryl C1-C2 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryloxy, heteroaryloxy C1-C2 alkyl , Heteroaryl C1-C2 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C2 alkyl, heterocyclyloxy, heterocyclyloxy C1-C2 Alkyl, heterocyclyl C1-C2 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C2)alkyl, heteroaryl-NR 21 -(C1-C2 ) Alkyl, heterocyclyl-NR 21 -(C1-C2)alkyl, wherein the last 35 groups mentioned are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C6 alkoxy C1-C2 alkoxycarbonyl;
R
21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-C2烷基；
R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;
R
22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-C2烷基；
R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;
m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;
其中，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，“杂芳基”是指
Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers to
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1、2或3个基团所取代的苯基、苄基、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-C2烷基、OR”、SR”、-(C1-C2)烷基-OR”、-(C1-C2)烷基-SR”、COR”、COOR”、COSR”、SOR”、SO
2R”、OCOR”、SCOR”，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-C2烷基、COR”、SO
2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基，以及-OCH
2CH
2-，-OCH
2O-，-OCH
2CH
2O-中的0、1、2或3个基团所取代；
Among them, it is selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl , C3-C6 cycloalkyl C1-C2 alkyl, OR", SR", -(C1-C2)alkyl-OR", -(C1-C2)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 ring Amino or aminocarbonyl substituted with one or two groups of alkyl C1-C2 alkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by 0, 1, 2 or 3 groups;
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-C8环烷基C1-C2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-C2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-C2烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C2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-C2烷基、C1-C6烷氨基羰基C1-C2烷基、三C1-C6烷基甲硅烷基、二C1-C6烷基膦酰基；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-C8 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy , C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C2 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyamino Carbonyl, C1-C6 alkoxycarbonyl C1-C2 alkyl, C1-C6 alkylaminocarbonyl C1-C2 alkyl, tri-C1-C6 alkylsilyl, di-C1-C6 alkylphosphono;
R”分别独立地代表氢，含有或不含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基或C3-C6环烷基C1-C2烷基。R" independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C2 alkyl with or without halogen .
进一步优选地，X代表S、SO或SO
2；
Further preferably, X represents S, SO or SO 2 ;
Y代表C2-C8烷基，卤代C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C8烷氧基C1-C8烷基，羟基C1-C8烷基，氰基，氰基C1-C8烷基，氨基C1-C8烷基，C1-C8烷氨基C1-C8 烷基，C1-C8烷基羰基，C3-C8环烷基，C3-C8环烷基C1-C8烷基，二C1-C8烷氨基羰基C1-C8烷基，C1-C8烷基羰基C1-C8烷基，C1-C8烷氧基羰基C1-C8烷基，C1-C8烷基羰基氧基C1-C8烷基，C1-C8烷基亚砜基C1-C8烷基，三C1-C8烷基硅氧基C1-C8烷基，杂环基，杂环基C1-C8烷基，苯基，杂芳基，杂芳基C1-C8烷基，-(C1-C8)烷基-O-N＝C(R”’)
2；
Y represents C2-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy C1-C8 alkyl, hydroxy C1-C8 alkyl, cyano, Cyano C1-C8 alkyl, amino C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, di-C1-C8 alkylaminocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy C1- C8 alkyl, C1-C8 alkylsulfoxide C1-C8 alkyl, tri-C1-C8 alkylsiloxy C1-C8 alkyl, heterocyclic, heterocyclic C1-C8 alkyl, phenyl, hetero Aryl, heteroaryl C1-C8 alkyl, -(C1-C8)alkyl-ON=C(R"') 2 ;
其中，杂环基为
杂芳基为未取代或被C1-C8烷基取代的
R”’分别独立地代表C1-C8烷基；
Among them, the heterocyclic group is Heteroaryl is unsubstituted or substituted by C1-C8 alkyl R"' independently represents C1-C8 alkyl;
Z代表氢，C1-C8烷基；Z represents hydrogen, C1-C8 alkyl;
M代表氢，C1-C8烷氧基羰基氧基C1-C8烷基；M represents hydrogen, C1-C8 alkoxycarbonyloxy C1-C8 alkyl;
优选地，X代表S、SO或SO
2；
Preferably, X represents S, SO or SO 2 ;
Y代表C2-C6烷基，卤代C1-C6烷基，C2-C6烯基，C2-C6炔基，C1-C6烷氧基C1-C6烷基，羟基C1-C6烷基，氰基，氰基C1-C6烷基，氨基C1-C6烷基，C1-C6烷氨基C1-C6烷基，C1-C6烷基羰基，C3-C6环烷基，C3-C6环烷基C1-C6烷基，二C1-C6烷氨基羰基C1-C6烷基，C1-C6烷基羰基C1-C6烷基，C1-C6烷氧基羰基C1-C6烷基，C1-C6烷基羰基氧基C1-C6烷基，C1-C6烷基亚砜基C1-C6烷基，三C1-C6烷基硅氧基C1-C6烷基，杂环基，杂环基C1-C6烷基，苯基，杂芳基，杂芳基C1-C6烷基，-(C1-C6)烷基-O-N＝C(R”’)
2；
Y represents C2-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, hydroxy C1-C6 alkyl, cyano, Cyano C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, di-C1-C6 alkylaminocarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy C1- C6 alkyl, C1-C6 alkyl sulfoxide C1-C6 alkyl, tri-C1-C6 alkylsiloxy C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, phenyl, hetero Aryl, heteroaryl C1-C6 alkyl, -(C1-C6)alkyl-ON=C(R"') 2 ;
其中，杂环基为
杂芳基为未取代或被C1-C6烷基取代的
R”’分别独立地代表C1-C6烷基；
Among them, the heterocyclic group is Heteroaryl is unsubstituted or substituted with C1-C6 alkyl R"' independently represents C1-C6 alkyl;
Z代表氢，C1-C6烷基；Z represents hydrogen, C1-C6 alkyl;
M代表氢，C1-C6烷氧基羰基氧基C1-C6烷基。M represents hydrogen, C1-C6 alkoxycarbonyloxy C1-C6 alkyl.
再进一步优选地，所述化合物优选为
基团Y、Z、M定义如前任一所述。
Still further preferably, the compound is preferably The definition of the groups Y, Z and M is as described above.
在上述通式I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-N(R
2)
2”中烷基可为-CH
2-、-CH
2CH
2-、-CH(CH
3)-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。
In the definition of the compound represented by the above general formula I and all the following structural formulas, the technical terms used, whether used alone or in compound words, represent the following substituents: alkyl groups having more than two carbon atoms may be straight-chain or Branched. For example, in the compound word "-alkyl-N(R 2 ) 2 ", the alkyl group may be -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )- and so on. The alkyl group is, 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 Group, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butylene -3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of 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. Similarly, cycloalkenyl is a monocyclic alkenyl having, for example, three to six carbocyclic members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where the double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.
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、
杂环基为含有3至6个环原子且还可通过苯并环稠合的、饱和的、部分饱和的或完全不饱和的环状基团，所述环原子中的1至4个(例如1、2、3、4个)杂原子选自氧、氮和硫。例如，杂环基包括但不限于具有0、1或2个氧代基团的
杂芳基为含有例如3至6个环原子且还可通过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、4个)杂原子选自氧、氮和硫。例如，杂芳基为
R’同上文中定义。
Unless otherwise specified, the "aryl" in the present invention includes but is not limited to phenyl, naphthyl, Heterocyclyl is a cyclic group containing 3 to 6 ring atoms, which can also be fused through a benzo ring, saturated, partially saturated or completely unsaturated, 1 to 4 of the ring atoms (eg 1, 2, 3, 4) heteroatoms are selected from oxygen, nitrogen and sulfur. For example, heterocyclic groups include but are not limited to those with 0, 1 or 2 oxo groups Heteroaryl is an aromatic cyclic group containing, for example, 3 to 6 ring atoms and also fused through a benzo ring, 1 to 4 of the ring atoms (e.g. 1, 2, 3, 4) Heteroatoms are selected from oxygen, nitrogen and sulfur. For example, heteroaryl is R'is as defined above.
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，如“N(R
2)
2”和“-烷基-N(R
2)
2”中的四个R
2基团独立地选自R
2所提及的那些基团，可相同也可不同，“Si(R
3)
3”中的三个R
3基团独立地选自R
3所提及的那些基团，可相同也可不同。
If 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. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, such as the four R 2 groups in "N(R 2 ) 2 "and "-alkyl-N(R 2 ) 2 " The groups are independently selected from those mentioned in R 2 and may be the same or different. The three R 3 groups in “Si(R 3 ) 3 ”are independently selected from those mentioned in R 3 , May be the same or different.
另外，除非特别限定地，本发明中多个并列取代基(以“、”或者“或”隔开)前述的限定词对其后每一个取代基都有限定作用，如“不含或含有卤素的烷基、烯基、炔基、环烷基”中“不含或含有卤素”对其后每一个基团“烷基”“烯基”“炔基”“环烷基”都有限定作用。In addition, unless otherwise specified, multiple parallel substituents (separated by "," or "or") in the present invention have the above-mentioned qualifiers for each subsequent substituent, such as "free or containing halogen" "Alkyl, alkenyl, alkynyl, cycloalkyl" in the "free or containing halogen" has a limiting role for each subsequent group "alkyl" "alkenyl" "alkynyl" "cycloalkyl" .
所述盐衍生物为通常的农药中使用的盐，例如，可以制成金属盐、胺盐、锍盐或鏻盐，或者，当分子中存在碱性部分时，可以制成例如硫酸盐、盐酸盐、硝酸盐、磷酸盐等的盐。当这些盐只要是作为农业、园艺用的除草剂使用时，也被包含在本发明中。本发明中，“金属盐”例如可以为碱金属盐、碱土金属盐、铝盐或铁盐。“碱金属盐”例如可以为，钠盐、钾盐或锂盐，优选为钠盐或钾盐。“碱土金属盐”例如可以为，钙盐或镁盐，优选为钙盐。本发明中，“胺盐”例如可以为，烷基仲胺盐、烷基叔胺盐或烷基季胺盐；烷醇伯胺盐、烷醇仲胺盐、烷醇叔胺盐或烷醇季胺盐；烷基烷醇伯胺盐、烷基烷醇仲胺盐、烷基烷醇叔胺盐或烷基烷醇季胺盐；或烷氧基烷醇伯胺盐、烷氧基烷醇仲胺盐、烷氧基烷醇叔胺盐或烷氧基烷醇季胺盐，优选地，其中所述烷基、烷醇和烷氧基团独立地为饱和的以及独立地含有C1-C4个碳原子，也可被苯基和/或卤素取代，更优选为单乙醇胺盐、二甲基乙醇胺盐、三乙醇胺盐、二甲胺盐、三乙胺盐、异丙胺盐、胆碱盐、二甘醇胺盐、
本发明中，“锍盐”“鏻盐”例如可以为，烷基锍盐、烷基鏻盐、烷醇鏻盐，优选地，其中所述烷基独立地为饱和的以及独立地含有C1-C4个碳原子，也可被苯基和/或卤素取代，更优选为
The salt derivative is a salt used in general pesticides, for example, it can be made into a metal salt, an amine salt, a sulfonium salt or a phosphonium salt, or, when there is a basic part in the molecule, it can be made into a sulfate salt Salts of acid salts, nitrates, phosphates, etc. These salts are also included in the present invention as long as they are used as herbicides for agriculture and horticulture. In the present invention, the "metal salt" may be, for example, an alkali metal salt, an alkaline earth metal salt, an aluminum salt, or an iron salt. The "alkali metal salt" may be, for example, a sodium salt, a potassium salt or a lithium salt, preferably a sodium salt or a potassium salt. The "alkaline earth metal salt" may be, for example, a calcium salt or a magnesium salt, preferably a calcium salt. In the present invention, the "amine salt" may be, for example, a secondary alkyl amine salt, a tertiary alkyl amine salt or a quaternary alkyl amine salt; Quaternary amine salt; primary alkyl alkoxy salt, secondary alkyl amine salt, tertiary alkyl amine salt or quaternary alkyl amine salt; or primary alkoxy alkoxy salt, alkoxy alkane Alcohol secondary amine salts, alkoxyalkanol tertiary amine salts or alkoxyalkanol quaternary amine salts, preferably, wherein the alkyl, alkanol and alkoxy groups are independently saturated and independently contain C1-C4 Carbon atoms, which may also be substituted by phenyl and/or halogen, more preferably monoethanolamine salt, dimethylethanolamine salt, triethanolamine salt, dimethylamine salt, triethylamine salt, isopropylamine salt, choline salt, Diethylene glycol amine salt, In the present invention, the "sulfonium salt" and the "phosphonium salt" may be, for example, alkylsulfonium salts, alkylphosphonium salts, alkanolphosphonium salts, preferably, wherein the alkyl group is independently saturated and independently contains C4 carbon atoms, which may also be substituted by phenyl and/or halogen, more preferably
本发明化合物的溶剂合物也包含在本发明中。Solvates of the compounds of the invention are also included in the invention.
根据取代基的性质和其被连接的方式，通式I的化合物可作为立体异构体存在。例如，如果存在一个或多个不对称碳原子或硫原子，则可出现对映异构体和非对映异构体。立体异构体可通过常规分离方法、例如通过色谱分离法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。本发明还涉及包含在通式I中但没有具体定义的所有立体异构体及其混合物。Depending on the nature of the substituents and the manner in which they are attached, the compounds of general formula I may exist as stereoisomers. For example, if one or more asymmetric carbon or sulfur 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.
一种所述的N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物的制备方法，包括以下步骤：A method for preparing the N-(1,3,4-oxadiazol-2-yl)aryl formamide compound includes the following steps:
a)当通式I中X代表Q时，其制备方法包括以下步骤：a) When X in the general formula I represents Q, the preparation method includes the following steps:
(1)使用化合物II与如通式III所示的化合物进行反应，制备如通式Ⅳ所示的化合物；(1) Using compound II to react with a compound represented by general formula III to prepare a compound represented by general formula IV;
(2)将如通式Ⅳ所示的化合物与二氧化碳反应，制得如通式Ⅴ所示的化合物；(2) The compound represented by the general formula IV is reacted with carbon dioxide to prepare the compound represented by the general formula V;
(3)在卤化剂的存在下，将如通式Ⅴ所示的化合物与Ⅵ所示的化合物反应制得如通式I-1所示的化合物；(3) In the presence of a halogenating agent, the compound represented by Formula V is reacted with the compound represented by Formula VI to prepare the compound represented by Formula I-1;
其反应方程式如下：The reaction equation is as follows:
其中，Q代表O、S或NR
1；
Among them, Q stands for O, S or NR 1 ;
优选地，所述步骤(1)反应在碱和溶剂的存在下进行；更优选地，所述碱选自NaOH、KOH中的一种或两种组合，所述溶剂选自DMF、DCM、DCE、ACN、THF、TFA中的一种及多种组合；所述反应温度为0～25℃；Preferably, the reaction in the step (1) is performed in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of NaOH and KOH, and the solvent is selected from DMF, DCM, DCE , ACN, THF, TFA one or more combinations; the reaction temperature is 0 ~ 25 ℃;
所述步骤(2)反应在催化剂和溶剂的存在下进行；优选地，所述催化剂为正丁基锂，所述溶剂选自THF、DMF、DCM、DCE、ACN、TFA中的一种及多种组合；所述反应温度为-100～-50℃；The reaction in the step (2) is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is n-butyl lithium, and the solvent is selected from one or more of THF, DMF, DCM, DCE, ACN, and TFA Combinations; the reaction temperature is -100 ~ -50 ℃;
所述步骤(3)反应在卤化剂、催化剂和溶剂的存在下进行；优选地，所述卤化剂为SOCl
2，所述催化剂为4-二甲氨基吡啶，所述溶剂为吡啶；所述反应温度为0～50℃。
The reaction in the step (3) is carried out in the presence of a halogenating agent, a catalyst and a solvent; preferably, the halogenating agent is SOCl 2 , the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine; the reaction The temperature is 0～50℃.
或者，b)当通式I中X代表S时，其制备方法包括如下步骤：Or, b) When X in the general formula I represents S, the preparation method includes the following steps:
依照上述如通式I-1所示化合物的制备方法制得如通式I-2所示的化合物，然后进行脱烷基反应；优选地，所述反应在溶剂的存在下；更优选地，所述溶剂选自DCM、DCE、ACN、DMF、THF、TFA中的一种或多种组合；所述反应温度为20～120℃；然后将制得的如通式Ⅶ所示的化合物与Hal-Y反应制备如通式I-3所示化合物；优选地，该反应在碱和溶剂的存在下进行；更优选地，所述碱选自碳酸钾、碳酸钠中的一种或两种组合，所述溶剂选自DCM、DCE、ACN、THF、DMF中的一种或多种组合；所述反应温度为0～25℃；The compound represented by the general formula I-2 is prepared according to the above preparation method of the compound represented by the general formula I-1, and then a dealkylation reaction is performed; preferably, the reaction is in the presence of a solvent; more preferably, The solvent is selected from one or more combinations of DCM, DCE, ACN, DMF, THF, and TFA; the reaction temperature is 20-120°C; and then the prepared compound represented by general formula VII and Hal -Y reaction to prepare a compound represented by general formula I-3; preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate The solvent is selected from one or more combinations of DCM, DCE, ACN, THF, and DMF; the reaction temperature is 0-25°C;
反应方程式如下：The reaction equation is as follows:
其中，Hal代表卤素，优选氟、氯或溴。Among them, Hal represents halogen, preferably fluorine, chlorine or bromine.
或者，c)当通式I中X代表SO、SO
2时，其制备方法包括如下步骤：
Or, c) When X in the general formula I represents SO and SO 2 , the preparation method includes the following steps:
将如通式I-3所示的化合物与过氧化物反应，制得如通式I-4和/或I-5所示的化合物；The compound represented by the general formula I-3 is reacted with peroxide to prepare the compound represented by the general formula I-4 and/or I-5;
反应方程式如下：The reaction equation is as follows:
优选地，所述过氧化物为
所述反应在溶剂的存在下进行；更优选地，所述溶剂选自DCM、DCE中的一种或两种组合；所述反应温度为0～50℃。
Preferably, the peroxide is The reaction is carried out in the presence of a solvent; more preferably, the solvent is selected from one or a combination of DCM and DCE; and the reaction temperature is 0-50°C.
或者，d)当通式I中M不为氢时，其制备方法包括如下步骤：Or, d) When M in general formula I is not hydrogen, the preparation method includes the following steps:
将如通式I-1、I-4、I-5所示的化合物与Hal-M反应，分别制得如通式I-6、I-7、I-8所示的化合物；Compounds represented by general formulas I-1, I-4, I-5 are reacted with Hal-M to prepare compounds represented by general formulas I-6, I-7, I-8, respectively;
反应方程式如下：The reaction equation is as follows:
优选地，所述反应在碱和溶剂的存在下进行；更优选地，所述碱选自碳酸钾、碳酸钠中的一种或两种组合，所述溶剂选自DCM、DCE、ACN、THF、DMF中的一种或多种组合，所述反应温度为0～100℃；Preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate, and the solvent is selected from DCM, DCE, ACN, THF , DMF one or more combinations, the reaction temperature is 0 ~ 100 ℃;
或者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4-二甲氨基吡啶，所述溶剂为吡啶，所述反应温度为0～80℃。Or the reaction is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is 4-dimethylaminopyridine, the solvent is pyridine, and the reaction temperature is 0-80°C.
一种除草组合物，包括(i)如通式I所示的N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物；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。A herbicidal composition comprising (i) an N-(1,3,4-oxadiazol-2-yl)aryl formamide compound represented by general formula I; preferably, it also includes (ii) One or more additional herbicides and/or safeners; more preferably, (iii) agrochemically acceptable formulation aids.
所述另外的除草剂包括以下化合物或其盐、酯等衍生物：The additional herbicides include the following compounds or their derivatives such as salts and esters:
a)ALS抑制剂：吡嘧磺隆(cas号：93697-74-6)、五氟磺草胺(cas号：219714-96-2)、双草醚(cas号：125401-92-5)、嘧草醚(cas号：147411-69-6)、嗪吡嘧磺隆(cas号：868680-84-6)、丙嗪嘧磺隆(cas号：570415-88-2)、氟酮磺草胺(cas号：874195-61-6)；a) ALS inhibitors: pyrazosulfuron-methyl (cas No.: 93697-74-6), penoxsulam (cas No.: 219714-96-2), bischlorfen (cas No.: 125401-92-5) , Pyrachlor (cas No.: 147411-69-6), pyrazosulfuron (cas No.: 868680-84-6), promethazine (cas No.: 570415-88-2), fluoromethoxazole Oxachlor (cas number: 874195-61-6);
b)ACCase抑制剂：氰氟草酯(cas号：122008-85-9)、噁唑酰草胺(cas号：256412-89-2)；b) ACCase inhibitors: cyflufenazone (cas No.: 122008-85-9), oxacarfen (cas no.: 256412-89-2);
c)激素类抑制剂：二氯喹啉酸(cas号：84087-01-4)、2甲4氯(cas号：94-74-6)、2,4-D(cas号：94-75-7)、2,4-D丁酸(cas号：94-82-6)、氯氟吡氧乙酸(cas号：69377-81-7)、氯氟吡啶酯(cas号：1390661-72-9)、2甲4氯丁酸(cas号：94-81-5)、麦草畏(cas号：1918-00-9)、二氯喹啉草酮(cas号：130901-36-8)、二氯吡啶酸(cas号：1702-17-6)、三氯吡氧乙酸(cas号：55335-06-3)；c) Hormone inhibitors: quinclorac (cas number: 84087-01-4), 2 methyl 4 chloro (cas number: 94-74-6), 2,4-D (cas number: 94-75- 7), 2,4-D butyric acid (cas number: 94-82-6), chlorofluoropyridine acetic acid (cas number: 69377-81-7), chlorofluoropyridine ester (cas number: 1390661-72-9 ), 2 methyl 4 chlorobutyric acid (cas number: 94-81-5), dicamba (cas number: 1918-00-9), diclofenac (cas number: 130901-36-8), dichloro Picolinic acid (cas number: 1702-17-6), triclofenac (cas number: 55335-06-3);
d)细胞***抑制剂：二甲戊灵(cas号：40487-42-1)、仲丁灵(cas号：33629-47-9)；d) Cell division inhibitors: pendimethalin (cas number: 40487-42-1), zhongdingling (cas number: 33629-47-9);
e)脂类合成(非ACC)抑制剂：禾草丹(cas号：28249-77-6)、禾草敌(cas号：2212-67-1)；e) Lipid synthesis (non-ACC) inhibitors: Hecaodan (cas No.: 28249-77-6), Hecao Di (cas no.: 2212-67-1);
f)HPPD抑制剂：***磺草酮(cas号：1911613-97-2)、双唑草酮(cas号：1622908-18-2)、环吡氟草酮(cas号：1855929-45-1)、硝磺草酮(cas号：104206-82-8)、双环磺草酮(cas号：156963-66-5)、呋喃磺草酮(cas号：473278-76-1)；f) HPPD inhibitors: chlorfenapyr (cas No.: 1911613-97-2), chlorfenapyr (cas No.: 1622908-18-2), ciprofloxan (cas No.: 1855929-45 1), mesotrione (cas No.: 104206-82-8), bicyclosulone (cas no.: 156963-66-5), furan sulcotrione (cas no.: 473278-76-1);
g)PDS抑制剂：吡氟酰草胺(cas号：83164-33-4)、氟咯草酮(cas号：61213-25-0)、氟丁酰草胺(cas号：113614-08-7)；g) PDS inhibitors: flufluramide (cas number: 83164-33-4), fluroxypyr (cas number: 61213-25-0), flubutachlor (cas number: 113614-08- 7);
h)PPO抑制剂：唑草酮(cas号：128621-72-7)、双唑草腈(cas号：158353-15-2)、噁草酮(cas号：19666-30-9)、丙炔噁草酮(cas号：39807-15-3)、乙氧氟草醚(cas号：42874-03-3)、环戊噁草酮(cas号：110956-75-7)；h) PPO inhibitors: chlorfenapyr (cas number: 128621-72-7), bisaclostrile (cas number: 158353-15-2), oxadiazon (cas number: 19666-30-9), propionic Oxachlor (cas No.: 39807-15-3), oxyfluorfen (cas No.: 42874-03-3), cyclopentachlor (cas No.: 110956-75-7);
i)长链脂肪酸合成抑制剂：丁草胺(cas号：23184-66-9)、丙草胺(cas号：51218-49-6)、苯噻酰草胺(cas号：73250-68-7)、莎稗膦(cas号：64249-01-0)、四唑酰草胺(cas号：158237-07-1)、异丙甲草胺(cas号：51218-45-2)、哌草磷(cas号：24151-93-7)、砜吡草唑(cas号：447399-55-5)；i) Long chain fatty acid synthesis inhibitors: butachlor (cas No.: 23184-66-9), alachlor (cas No.: 51218-49-6), fenclofen (cas No.: 73250-68- 7), sartorine (cas No.: 64249-01-0), tetrazolamide (cas no.: 158237-07-1), metolachlor (cas no.: 51218-45-2), piper Glufosinate (cas number: 24151-93-7), sulfometramid (cas number: 447399-55-5);
j)PSⅡ抑制剂：西草净(cas号：1014-70-6)、扑草净(cas号：7287-19-6)、胺唑草酮(cas号：129909-90-6)、异丙隆(cas号：34123-59-6)、除草定(cas号：314-40-9)、哒草特(cas号：55512-33-9)、绿麦隆(cas号：15545-48-9)、灭草松(cas号：25057-89-0)、敌稗(cas号：709-98-8)、嗪草酮(cas号：21087-64-9)、莠去津(cas号：1912-24-9)、溴苯腈(cas号：1689-84-5)、辛酰溴苯腈(cas号：1689-99-2)、特丁津(CAS号：5915-41-3)；j) PSⅡinhibitors: Xicaojing (cas No.: 1014-70-6), promethazin (cas no.: 7287-19-6), azatrochlor (cas no.: 129909-90-6), iso Binglong (cas No.: 34123-59-6), herbicide (cas no.: 314-40-9), dacao te (cas no.: 55512-33-9), chloromeron (cas no.: 15545-48 -9), bentazone (cas No.: 25057-89-0), diarrhea (cas No.: 709-98-8), diazepam (cas No.: 21087-64-9), atrazine (cas No.: 1912-24-9), bromoxynil (cas number: 1689-84-5), octanoyl bromoxynil (cas number: 1689-99-2), terbutin (CAS number: 5915-41- 3);
k)DOXP抑制剂：异噁草松(cas号：81777-89-1)；k) DOXP inhibitor: clomazone (cas number: 81777-89-1);
l)其他：噁嗪草酮(cas号：153197-14-9)、环庚草醚(cas号：87818-31-3)、茚草酮(cas号：133220-30-1)。l) Others: Oxachlor (cas number: 153197-14-9), cycloheptachlor (cas number: 87818-31-3), indoxazone (cas number: 133220-30-1).
在本说明书的上下文中，如果使用活性化合物的通用名称的缩写形式，则在每种情况下包括所有的常规衍生物，例如酯和盐，以及异构体，特别是光学异构体，特别是一种或多种市售形式。如果通用名称表示酯或盐，则在每种情况下还包括所有其他的常规衍生物，例如其他的酯和盐、游离酸和中性化合物，以及异构体，特别是光学异构体，特别是一种或多种市售形式。给出的化合物的化学名称表示至少一种被通用名称涵盖的化合物，通常是优选的化合物。在磺酰胺如磺酰脲的情况下，盐还包括通过阳离子与磺酰胺基团中的氢原子交换而形成的盐。例如，2,4-D或2,4-D丁酸衍生物包含但不限于：2,4-D或2,4-D丁酸盐如钠盐、钾盐、二甲铵盐、三乙醇铵盐、异丙胺盐、胆碱等，以及2,4-D或2,4-D丁酸酯如甲酯、乙酯、丁酯、异辛酯等；2甲4氯衍生物包含但不限于：2甲4氯钠盐、钾盐、二甲铵盐、异丙胺盐等，以及2甲4氯甲酯、乙酯、异辛酯、乙硫酯等。In the context of this specification, if the abbreviated form of the common name of the active compound is used, then in each case all conventional derivatives, such as esters and salts, as well as isomers, especially optical isomers, especially One or more commercially available forms. If the generic name denotes an ester or salt, then in each case also include all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, especially optical isomers, especially It is one or more commercially available forms. The chemical names of the compounds given represent at least one compound covered by a common name, and are generally preferred compounds. In the case of sulfonamides such as sulfonylurea, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group. For example, 2,4-D or 2,4-D butyric acid derivatives include but are not limited to: 2,4-D or 2,4-D butyrate such as sodium salt, potassium salt, dimethylammonium salt, triethanol Ammonium salts, isopropylamine salts, choline, etc., and 2,4-D or 2,4-D butyrate esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.; 2 methyl 4 chloro derivatives include but not Limited to: 2 methyl 4 chloro sodium salt, potassium salt, dimethyl ammonium salt, isopropyl amine salt, etc., and 2 methyl 4 chloro methyl ester, ethyl ester, isooctyl ester, ethyl thioester, etc.
一种控制杂草的方法，包括将除草有效量的所述的N-(1,3,4-噁二唑-2-基)芳基甲酰胺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，优选地，所述植物为水稻(如籼稻、粳稻)，所述杂草为禾本科杂草(如稻稗、千金子、稗草、马唐、狗尾草)、阔叶杂草(如鸭舌草、野慈菇、苘麻、反枝苋、繁缕)、莎草科杂草(如异型莎草、萤蔺)。A method for controlling weeds, which comprises weeding an effective amount of at least one of the N-(1,3,4-oxadiazol-2-yl)arylformamide compounds or the herbicide The agent composition is used on plants or weed areas. Preferably, the plant is rice (such as indica rice, japonica rice), and the weed is gramineous weed (such as rice barnyardgrass, Qianjinjin, barnyard grass, horse tang, Setaria), broad-leaved weeds (such as gazania, wild mushrooms, velvetleaf, amaranth, chickweed), sedge weeds (such as sedge, fireflies).
所述的N-(1,3,4-噁二唑-2-基)芳基甲酰胺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N-(1,3,4-噁二唑-2-基)芳基甲酰胺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，所述作物为水稻(如籼稻、粳稻)，所述杂草为禾本科杂草(如稻稗、千金子、稗草、马唐、狗尾草)、阔叶杂草(如鸭舌草、野慈菇、苘麻、反枝苋、繁缕)、莎草科杂草(如异型莎草、萤蔺)。The use of at least one of the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compounds or the herbicide composition for controlling weeds, preferably, The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound is used to control weeds in useful crops, which are genetically modified crops or genome editing techniques Crops, the crops are rice (such as indica rice, japonica rice), the weeds are gramineous weeds (such as rice barnyardgrass, Qianjin, barnyardgrass, crabgrass, green bristlegrass), broad-leaved weeds (such as duckweed , Wild champignons, velvetleaf, Amaranthus retroflexus, Stellaria), sedge grass weeds (such as sedge, firefly).
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。For many economically important monocotyledonous and dicotyledonous harmful plants, the compounds of formula I according to the invention have outstanding herbicidal activity. The active substances of the present invention are 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. Examples of weed species where the active substance works effectively include monocotyledons: annual oats, rye, grass, hordeum, ferraris, barnyardgrass, crabgrass, foxtail and sedge, and perennial ice Grasses, bermudagrass, chrysanthemum and sorghum, and perennial sedges.
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、***婆婆纳、三色堇和苋、猪殃殃属和地肤。Regarding dicotyledonous weed species, the effects of which can be extended to species such as the annual Swine, 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, Cicus, Alisma, water chestnut, cane grass, and sedge, under such predetermined conditions as rice seeding. If the compound of the present invention is applied to the soil surface before germination, the weed seedlings can be completely prevented before the weeds grow, or they can stop growing when the weeds 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 grass, Ono sesame, Polygonum sibiricum, Stellaria, Ivy leaf Pompa, Arab Pompa, Pansy and Amaranthus, Swamp, and Kochia .
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。Although the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are 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.
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。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 usually 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.
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。The compounds of the formula I or salts thereof of the present invention 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 beets, 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 resistant to the toxic effects of the herbicides through genetic engineering.
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：Conventional methods for breeding plants with improved shapes compared to known plants include, for example, traditional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained by means of genetic engineering (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described:
-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)；-In order to improve starch synthesis in plants, genetic engineering is used to change crop plants (eg 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)；-Transgenic crop plants that are resistant to specific herbicides, to glufosinate herbicides (eg EP-0242236 A, EP-0242246 A) or to glyphosate herbicides (WO 92/00377), or Acyl urea herbicides (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)；-Transgenic crop plants such as cotton, which can produce Bacillus thuringiensis toxin (Bt toxin), this toxin can protect plants against specific pests (EP-0142924A, EP-0193259A);
-具有改进的脂肪酸成份的转基因作物植物(WO91/13972)。-Transgenic crop plants with improved fatty acid composition (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。Many molecular biotechnologies that can produce transgenic plants with improved traits are known (see, for example, Sambrook et al., 1989, Molecular Amplification, Second Handbook of Experiments, Published by Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker "Gene Kunde "[Genes and Cloning], VCH Weinheim, Second Edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431)). In order to realize the operation of genetic engineering, a nucleic acid molecule may be introduced into a plasmid, and mutation or sequence change may occur through recombination of DNA sequences. Using the standard methods described above, for example, it is possible 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 binders or linkers to the fragments.
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。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-mentioned gene products.
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。For this purpose, it is possible to use 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.
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)。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).
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。Transgenic plant cells can be recombined into whole plants using known techniques. The transgenic plant can be any desired plant variety, namely monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (=natural) genes or gene sequences, or by expressing heterogeneous (=external) genes or gene sequences.
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。When using the active substance of the present invention on genetically modified crops, in addition to the observable effects on other crops of suppressing harmful plants, there will often be special effects on the corresponding genetically modified crops, for example, to improve or expand control 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.
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。In addition, 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.
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。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. Thus 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. Examples of suitable formulation choices are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), 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) formulas, microcapsules and wax products. These individual formulation types are known and described in documents such as Winnacker-Küchler, "Chemische Techonologie" [Chemical Process], Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade Vank Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" manual, 3rd edition 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。
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. Marsden's "Solvent Guide" Second Edition, Interscience, NY1963; McCutcheon's "Detergents and Emulsifiers" Annual Report, MC Publishing Company, Ridgewood NJ; Sisley and Wood, "Surface Encyclopedia", Chemical Publishing Company, NY1964; of [Ethylene oxide adduct surfactant], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler's "Chemische Technologie" [Chemical Process], Volume 7, C. Hauser Verlag Munich, 4th edition 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。Wettable powders can be uniformly dispersed in water. In addition to active substances, they also include diluents or inert substances, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, poly Ethoxy fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2,2'-dinaphthyl methane Sodium -6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoyl methyl taurine. For the preparation of wettable powders, the active substances of the herbicides are finely ground, for example using commonly used equipment, such as hammer mills, fan mills and jet mills, and the adjuvants are mixed simultaneously or sequentially.
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。Dissolve the active substance in an organic solvent to prepare a concentrated emulsion, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and add one more One or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are 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.
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。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. The suspension 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 the other formulation type described above.
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。To prepare an emulsion such as an oil-in-water emulsifier (EW), 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.
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。Use the following method to prepare granules, spray the active material onto the adsorbate, granulate with inert materials, or concentrate the active material onto the surface of a carrier such as sand or kaolinite, granulate the inert materials through a binder, and 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.
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。For the preparation methods using grinding discs, fluidized beds, extruders and spray granules, see the following processes, such as "Spray Drying Manual" Third Edition 1979, G. Goodwin Ltd., London; JEBrowning, "Agglomeration", Chemistry and Engineering 1967, p. 147ff; "Perry's Chemistry Engineer's Handbook", Fifth Edition, McGraw-Hill, New York 1973, p. 8-57. If you want to know about the formulation of crop protection products, see, for example, GCKlingman, “Weed Controls as Science”, John Wiley and Sons, New York, pp. 81-96, and JDFreyer, SAEvans “Weed Control Manual”, Fifth Edition, Blackwell Scientific Rubblications, Oxford University 1968, pages 101-103.
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。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 the active substance in the water-suspended granules, it mainly depends on whether the active substance is liquid or solid, and the additives, 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.
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。In addition, 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.
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。Based on these preparations, it may also be mixed with other insecticide active substances such as insecticides, acaricides, herbicides and fungicides, and may also be mixed with safeners, fertilizers and/or plant growth regulators, the mixing method may be For pre-mixing or filling and mixing.
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、环戊噁草酮、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、***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，LS 82-556、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。In a compound preparation or a tank-mix preparation, suitable active substances that can be mixed with the active substances 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. For example, 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, propachlor, metolachlor, sinoprofen, alachlor, alachlor, toxachlor, cyproteron, naproxen, R-levonal Alachlor, Dipropanil, fenclofen, difenochlor, fenfluramide, alafenamide, flufenacetamide, bromobutanil, dimethyl thiazopyr, high-efficiency dimethyl Tetrachlor, ethoxyfen, chlorfenapyr, tetromethoxam, metazachlor, clomazone, high-efficiency methyl strawgrass, high-efficiency propylpropoxylate, dimethochlor, dimethoprim , Butachlor, cyproteron, flufenachlor, heptachlor, isobutachlor, propachlor, terbutachlor, xylolachlor, dimethylchlor, alachlor, Trimechlor, chloroformamide, cyproteron, valerox, chloramphenicol, neoyanlin, tricyclachlor, butenochlor, forage, benzalkonium, quinone Phenylamine, fenfluramide, naproxen, acetochlor, naphthachlor, chlorfenapyr, pymetrozine, benomyd, oxamethoxazole, chlorophthalimide, butamidide, fluroxypyr Amine, atrazine, simazine, promethazine, cyanochlor, acetochlor, atrazine, promethazine, isopropyl, fluroxypyr, terbutaline, terbutazone, triazine fluoxamol , Ciprofloxacin, Gampuzin, Caodajin, Promethazine, Cimaton, Azidene, Diquat, Isoprolate, Ciprofloxacin, Methazone, Another Dingjin, Zhongdingtong, Special Ding Tong, Methoxypropyl, Cyanoxystrobin, Imazuron, Clotin, Atrazine, Benzotrin, Glycyrazine, Cyanuric Acid, Indaziflam, Green Suluron, Metsulfuron, Bensulfuron, Chlorine Pysulfuron-methyl, besulfuron-methyl, thisulfuron-methyl, pyrisulfuron-methyl, methyldisulfuron-methyl, methyl iodosulfuron-methyl sodium salt, formamidosulfuron-methyl, ethersulfuron-methyl, ethersulfuron-methyl, sulfometuron-methyl Chlorsulfuron, nicosulfuron, trisulfuron, acrimsulfuron, ethoxysulfuron, cyprosulfuron, sulfasulfuron, tetrazosulfuron, pyrimsulfuron, monosulfuron, Monosulfuron, fluorosulfuron, fluoropyrsulfuron, fluoropyrsulfuron, epoxypyrsulfuron, oxasulfuron, fluorosulfuron, profensulfuron, trifluorosulfuron, Sulsulfuron-methyl, triflusulfuron-methyl, flusulfuron-methyl, trifomesulfuron-methyl, metsulfuron-methyl sodium salt, flufensulfuron-methyl, sulfasulfuron-methyl, pyrimethanuron-sulfuron, propyrisulfuron (promethazine Long), azimesulfuron, triflufenazone, fluoxafen, milflurazine, acetoflufen, acetoflufen, ethoxyfop-methyl, gluconate, befenazone, chlorflufen Ethyl acetate, mecarboxyl ether, triflufon-methyl, methoxytrimfon, triflufoxyn, fluorinated herbicidal ether, fluroxypyr, herbicidal ether, acetochlor, dimethoate, fluoroester oxime Glufosinate, fluroxypyr, Halosafen, chlormeron, isoproturon, rifauron, diuron, sapron, fluroxon, phendiuron, metsulfuron, bensulfuron, sulfathion Long, Isoxuron, Tebusulfuron, Ethylsulfuron, Chlorosulfuron, Methylsulfuron, Fensulfuron, Metochlor, Bromulon, Methonon, Green Valley Long, Huancaolong, Fecaolong, Fluorine Thiuron, chlorpyrrolone, chlorpyrifos, cyprosulfuron, isoproturon, cyclosulfuron, teflon, thidiazuron, trosulfuron, p-fiuron, methamidozone, carbosulfur, trimethoprim, Oxazolon, Monisouron, Anisuron, Methiuron, Chloreturon, Teflon, Betaine, Betaine-Ethyl, Betaine, Sulforazone, Tepronil, Oatrol, Anilin, Chloramphenicol, Diclofenac Ester, chlorpyrifos, chlorhexidine, Carboxazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, butachlor, cyproteron, chlorpyrifos, cyproteron, dicamba, piperazine, cypermethrin, barnyardgrass Caodan, Huancaodi, Oatmeal, Bentachlor, Ethiopyr, Pingcaodan, Kecaomeng, benzalkonium, zhongcaodan, thiomethalin, chlorpyrifos, Isopolinate, Methiobencarb, 2, 4-drop butyl ester, 2 methyl 4 sodium chloride, 2,4-D isooctyl ester, 2 methyl 4 chloro isooctyl ester, 2,4-D sodium salt, 2,4-D dimethylamine salt, 2 A 4 Ethyl chloride, 2 methyl 4 chloro, 2,4-D propionic acid, high 2,4-D propionate, 2,4-D butyric acid, 2 methyl 4 chloropropionic acid, 2 methyl 4 chloropropionate , 2 methyl 4-chlorobutyric acid, 2,4,5-dipyrane, 2,4,5-dipropionic acid, 2,4,5-dibutyric acid, 2 methyl-4 chloramine salt, dicamba, chlorfenapyr, Valerac, saison, triclosan, trichlorobenzoic acid, trimethoprim, chlorpyrifos, diflufenicol, diflufenicol, diflufenar, diflufenicol, high-efficiency pyrimidine Fluclomethol, quizalofop, quizalofop, oxaflufen, oxamethoxam, oxamethoxam, cyflufenazone, oxachlor, cyprodin, thiazofazone , Cypromethrin, oxypentalin, triflufenazone oxime, clomazone, paraquat, diquat, acesulfame, ethamfluran, isoprofen, mesotrimethrin, ciprofloxacin Fipron, Amifoprin, Ethflurane, Chlorethoprim, Amethoprim, Difluralin, Chlordifloxacin, Methalpropalin, Propofol, Glyphosate, Sarcofosine, Glufosinate , Methylamine glufosinate, glufosinate, glufosinate, bisphosphinate, diphosphazin, glufosinate, glufosinate, valerosin, dimeglufosin, glufosinate, imidazole nicotinic acid, imidazole nicotinic acid , Imidazoquinolinic acid, methoxamethoxam, methoxazone ammonium salt, methoxazole nicotinic acid, imazamate, chlorofluoropyroxyacetic acid, chlorofluoropyroxyacetic acid isooctyl ester, diclofenac, ammonia Clopyralid, triclofenac, fluroxypyr, fluroxypyr, triclofenol, thiacloprid, fluroxypyr, clopyralid, fluroxypyr, triclofenac butoxy Ethyl ethyl ester, Cliodinate, diclofenac, clethodim, chlorfenapyr, chlorfenapyr, ciclofenone, bufofenone, oxadiazon, pyranone, buthidazole, imazalone, cycloazinone , Fenoxazone, acetochlor, Ametridione, Amibuzin, bromoxynil, octanoyl bromoxynil, octanoyl iodile nitrile, iodobenzonitrile, diquat, diphenylacetonitrile, bisacrylonitrile, hydroxydimethicone Oxynitrile, Iodobonil, azole Sulfamethoxam, alafenamide, penoxsulam, sulfoxazosin, chlorfenazone, alafenamide, alafenamide, fluoxaron, dimefen, pyrimethanil Ethers, cyclic esters of glufosinate, pyraclostrobin, azoxystrobin, bicyclosulone, mesotrione, sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxachlor, clomazone, Fenoxasulfone, Methiozolin, Ipramethoxam, Mepyrazine, Pyrazolate, Wild Paraquat, Benzoconazole, Metazarone, Pyclofen, Pyrasulfotole, Oxachlor, Pyroxasulfone, Pyraclostrobin, Fluoxamide Oxaconazole, trimethoprim, chlorfenapyr, chlorpyrifosin, fluoxazone, mesotrione, Bencarbazone, fenflurazine, fluoxaprofen, herbicide, clomazone, clomazone Pyridinium, Tetradinium, Flupropacil, Indoxachlor, Flufenoxalic Acid, Propyrhyflur, Mepyramine, Phthalate, Flumezin, Pentachlorophenol (Sodium), Dylenol, Tetral, Tetral Oxalate, pentolphenol, dinitrophenol, chlorophenol, diloxate, diloxate, propynyl oxadiazone, oxadiazone, cyclopentazone, fluoxazone, methyl oxalate, tetramethoate Oxachlor, flupyrazine, fenpyrifos, bromochlor, dimethal, fenpyr, fenpyr, pyridone, pyrazine, pyrrazine, pyridafol, quinclorac, chlormethalin Quinolinic acid, bendazon, dapyrazine, oxachlor, chlorfenapyr, clomazone, cyprofen, isopropyl chlorfen, propyl fenpyr, indoxazone, sodium chlorate, Thatch, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage fast, bromophenol oxime, triazole sulfonate, trimethoxazole, furoxazone, furosemide, acetosulfur, pyrimethanil Amine, chlorophthalic acid, fluroxypyr, barnyardgrass, acrolein, benzeben, chlorfenapyr, oat ester, thiadiazolamide, trimethoprim, hypromone, oxybenzone, benzoin Sulfentrazone, chlorfenapyr, trichloropropionic acid, Alorac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, sulfamethoxazole, Cambendichlor, cyclopyrimidine acid, thiocyanate Aniline, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, acetonitrile, oxazane, oxazalil, oxazin, pyrazolin, pyrazolin, Oximepyral, bisoxazolic acid, dichloropropenylamine, fluorochloropyridinium ester, DOW chlorofluoropyridinium ester, UBH-509, D489, LS 82-556, 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 and 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/ha之间，或更多的活性物质，但优选在0.005到750g/ha之间，特别是在0.005到500g/ha之间。When used, if necessary, the commercially available formulations are diluted in a 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. As 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.
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。The following examples are used to illustrate the present invention and should not be considered as limiting the present invention in any way. The scope of the claimed rights of the present invention is described by the claims.
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A1-A152中。具体的化合物结构及相应的化合物信息如表A1和表1所示。表A1-A152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。In view of the economics and diversity of the compounds, we prefer to synthesize some compounds. Among the many compounds synthesized, selected parts are listed in the following tables A1-A152. The specific compound structure and corresponding compound information are shown in Table A1 and Table 1. The compounds in Tables A1-A152 are only for better description of the present invention, but do not limit the present invention. For those skilled in the art, it should not be understood that the scope of the above subject matter of the present invention is limited to the following compounds.
表A1化合物结构及其
1HNMR数据
Table A1 Compound structure and its 1 HNMR data
表A2以与表A1相同的方式构造，除了“Z”列下面的条目被下文所示的相应“Z”列条目替代。因此，表A2中的第一条目是化合物2-1(其中X为S，Y为Me，Z为Et，M为H)，依次为化合物2-2、化合物2-3、化合物2-4……最后一个条目是化合物2-661。表A3至A152类似地构造。Table A2 is constructed in the same manner as Table A1, except that the entries below the "Z" column are replaced by the corresponding "Z" column entries shown below. Therefore, the first entry in Table A2 is compound 2-1 (where X is S, Y is Me, Z is Et, and M is H), followed by compound 2-2, compound 2-3, compound 2-4 ...The last entry is compound 2-661. Tables A3 to A152 are constructed similarly.
其中，上述表格中部分化合物的
1HNMR数据如下表1：
Among them, the 1 HNMR data of some compounds in the above table are as follows in Table 1:
表1.化合物
1HNMR数据
Table 1. Compound 1 HNMR data
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。Several methods for preparing the compounds of the present invention are explained in detail in the following schemes and examples. The raw materials are commercially available or can be prepared by methods known in the literature or as shown in the detailed explanation. Those skilled in the art should understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific raw materials and conditions in the synthetic route have been described in the following, they can be easily replaced with other similar raw materials and conditions, such as those produced by the modification or modification of the preparation method of the present invention, such as compounds Various isomers and the like are included in the scope of the present invention. In addition, the preparation method described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, the protection of appropriate groups during the reaction and so on.
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。The method examples provided below are used to promote a further understanding of the preparation method of the present invention. The specific substances, types and conditions used are determined to be a further description of the present invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds indicated in the table below are either commercially available or can be easily prepared by those of ordinary skill in the art.
代表性化合物的实施例如下：Examples of representative compounds are as follows:
1、化合物1-4的合成1. Synthesis of Compounds 1-4
(1)在30毫升的DMF中依次加入Ⅱ(3g,16mmol,1.0eq)，NaOH(0.72g,18mmol,1.1eq)然后在0℃条件下逐滴加入a(1.07g,1.2mmol,1.05eq)，然后反应液在0℃条件下搅拌1小时。LCMS检测显示原料基本反应完毕，有一个主要的新峰。将反应液倒入30毫升水中，分液，水相用50毫升乙酸乙酯萃取一次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到b(3.4g,92％收率)(无色的油)。(1) Add Ⅱ (3g, 16mmol, 1.0eq), NaOH (0.72g, 18mmol, 1.1eq) to 30ml of DMF in sequence, then add a (1.07g, 1.2mmol, 1.05eq) dropwise at 0℃ ), and then the reaction solution was stirred at 0°C for 1 hour. LCMS detection showed that the raw materials had basically reacted and there was a major new peak. The reaction solution was poured into 30 ml of water, and the layers were separated. The aqueous phase was extracted once with 50 ml of ethyl acetate. The organic phase was washed three times with saturated brine (50 ml), dried, spin-dried, and separated by column chromatography to obtain b (3.4 g, 92% yield) (colorless oil).
(2)在30毫升的THF中加入b(3g,13mmol,1.0eq)，然后在-78℃条件下缓慢加入n-BuLi(6.42ml,2.5M,16mmol,1.2eq)，然后反应液在-78℃条件下搅拌0.5小时后缓慢通入CO
2，通入10min后反应液缓慢升到室温。LCMS检测到产品。往反应液中倒入20毫升水，分液，水相用30毫升乙酸乙酯萃取一次，水相用浓盐酸逐渐调到pH＝4-5，过滤，干燥得到c(3g,83.6％收率)(白色固体)。
(2) Add b (3g, 13mmol, 1.0eq) to 30ml of THF, then slowly add n-BuLi (6.42ml, 2.5M, 16mmol, 1.2eq) at -78°C, and then After stirring at 78°C for 0.5 hours, CO 2 was slowly introduced, and after 10 minutes, the reaction solution was slowly raised to room temperature. LCMS detected the product. Pour 20 ml of water into the reaction solution, separate the layers, extract the aqueous phase once with 30 ml of ethyl acetate, adjust the aqueous phase to pH=4-5 with concentrated hydrochloric acid, filter, and dry to obtain c(3g, 83.6% yield) ) (White solid).
(3)在30毫升的吡啶中依次加入c(3g,11mmol,1.0eq)，d(1.66g,16.8mmol,1.5eq),DMAP(0.13g,1.1mmol,0.1eq)。然后在0℃条件下缓慢加入SOCl
2(2.0g,16.8mmol,1.5eq)，然后反应液在室温条件下搅拌3小时。LCMS检测到产品。浓缩除掉吡啶后往反应液倒入30毫升水，分液，水相用30毫升乙酸乙酯萃取三次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到化合物1-4(2.5g,64％收率)(白色固体)。
(3) C (3g, 11mmol, 1.0eq), d (1.66g, 16.8mmol, 1.5eq), DMAP (0.13g, 1.1mmol, 0.1eq) were added to 30ml of pyridine sequentially. Then, SOCl 2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0°C, and then the reaction solution was stirred at room temperature for 3 hours. LCMS detected the product. After removing pyridine by concentration, pour 30 ml of water into the reaction solution to separate the liquid. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried and separated by column chromatography. Compound 1-4 (2.5 g, 64% yield) (white solid).
2、化合物1-5的合成2. Synthesis of Compounds 1-5
在10毫升的二氯甲烷中依次加入1-4(1g,2.8mmol,1.0eq)，e(0.54g,3.1mmol,1.1eq)。然后反应液在室温条件下搅拌1小时。LCMS检测到产品，原料基本反应完毕。将反应液倒入10毫升水中，用亚硫酸氢钠淬灭，分液，水相用30毫升二氯甲烷萃取三次，有机相用饱和食盐水(30ml)洗一次，干燥，旋干，柱层析分离得到化合物1-5(0.8g,76.5％收率)(灰白色的固体)。To 10 ml of dichloromethane was added 1-4 (1 g, 2.8 mmol, 1.0 eq), e (0.54 g, 3.1 mmol, 1.1 eq) in sequence. The reaction solution was then stirred at room temperature for 1 hour. LCMS detected the product, and the raw materials were basically reacted. The reaction solution was poured into 10 ml of water, quenched with sodium bisulfite, and the solution was separated. The aqueous phase was extracted three times with 30 ml of dichloromethane. The organic phase was washed once with saturated brine (30 ml), dried, and spin-dried. The compound 1-5 (0.8 g, 76.5% yield) (off-white solid) was obtained by analytical separation.
3、化合物1-6的合成3. Synthesis of Compound 1-6
在10毫升的二氯甲烷中依次加入1-4(1g,2.8mmol,1.0eq)，e(1.24g,7.2mmol,2.5eq)。然后反应液在室温条件下搅拌24小时。LCMS检测到产品，原料基本反应完毕。过滤之后将氯液用亚硫酸氢钠淬灭，浓缩之后柱层析分离得到化合物1-6(0.5g,45.8％收率)(灰 白色的固体)。To 10 ml of dichloromethane were added 1-4 (1 g, 2.8 mmol, 1.0 eq), e (1.24 g, 7.2 mmol, 2.5 eq) in sequence. The reaction solution was then stirred at room temperature for 24 hours. LCMS detected the product, and the raw materials were basically reacted. After filtration, the chlorine solution was quenched with sodium bisulfite, concentrated, and separated by column chromatography to obtain compound 1-6 (0.5 g, 45.8% yield) (off-white solid).
4、化合物1-69的合成4. Synthesis of Compound 1-69
(1)采用上述化合物1-4的合成方法制得化合物1-136，然后在5毫升的TFA中加入1-136(0.34g,1.0mmol,1.0eq)，然后反应液在90℃条件下搅拌16小时。LCMS检测到产品，旋干，得到A(0.29g)(黄色油状，粗品)。(1) Compound 1-136 was prepared by the above synthesis method of compound 1-4, then 1-136 (0.34 g, 1.0 mmol, 1.0 eq) was added to 5 mL of TFA, and then the reaction solution was stirred at 90°C 16 hours. The product was detected by LCMS and spin-dried to give A (0.29g) (yellow oil, crude).
(2)在10毫升的DMF中依次加入A(0.32g,1.0mmol,1.0eq)，K
2CO
3(0.28g,2mmol,2.0eq)和B(0.13g,1.1mmol,1.1eq)，然后反应液在25℃条件下搅拌2小时。LCMS检测到产品。将反应液倒入20毫升水中，分液，水相用20毫升乙酸乙酯萃取三次，有机相用饱和食盐水(20ml)洗3次，干燥，旋干，柱层析分离得到化合物1-69(0.25g,69％收率)(白色固体)。
(2) Add A (0.32g, 1.0mmol, 1.0eq), K 2 CO 3 (0.28g, 2mmol, 2.0eq) and B (0.13g, 1.1mmol, 1.1eq) to 10ml of DMF in sequence, then The reaction solution was stirred at 25°C for 2 hours. LCMS detected the product. The reaction solution was poured into 20 ml of water, and the layers were separated. The aqueous phase was extracted three times with 20 ml of ethyl acetate. The organic phase was washed three times with saturated brine (20 ml), dried, spin-dried, and separated by column chromatography to obtain compound 1-69. (0.25g, 69% yield) (white solid).
5、化合物1-112的合成5. Synthesis of Compound 1-112
化合物1-4(500mg，1.4mmol)，化合物C(367mg，2.1mmol)，碳酸钾(595mg，2.8mmol)，乙腈10mL置于圆底烧瓶中，80℃下搅拌12小时。高效液相色谱检测反应结束后，降温至20℃，将反应体系过滤掉剩余碳酸钾固体，母液直接经prep-HPLC分离，得到化合物1-112(160mg，收率25％，白色固体)。Compound 1-4 (500 mg, 1.4 mmol), compound C (367 mg, 2.1 mmol), potassium carbonate (595 mg, 2.8 mmol), and acetonitrile 10 mL were placed in a round bottom flask and stirred at 80°C for 12 hours. After the reaction was detected by high performance liquid chromatography, the temperature was lowered to 20°C, the reaction system was filtered to remove the remaining potassium carbonate solid, and the mother liquor was directly separated by prep-HPLC to obtain compound 1-112 (160 mg, yield 25%, white solid).
6、化合物1-118的合成6. Synthesis of Compound 1-118
化合物1-4(500mg，1.4mmol)，催化量的4-二甲氨基吡啶(10mg)，吡啶5mL置于圆底烧瓶中，加热至60℃，氮气保护下缓慢滴加化合物D(1.1g，7.0mmol)。高效液相色谱检测反应结束后，降温至20℃，将反应体系浓缩后经prep-HPLC分离，得到化合物1-118(150mg，收率22％，黄色固体)。Compound 1-4 (500mg, 1.4mmol), a catalytic amount of 4-dimethylaminopyridine (10mg), pyridine 5mL was placed in a round bottom flask, heated to 60 ℃, slowly dropwise under the protection of nitrogen compound D (1.1g, 7.0 mmol). After detecting the completion of the reaction by high performance liquid chromatography, the temperature was lowered to 20°C, and the reaction system was concentrated and then separated by prep-HPLC to obtain compound 1-118 (150 mg, yield 22%, yellow solid).
7、化合物1-127的合成7. Synthesis of Compound 1-127
(1)在30毫升的DMF中依次加入Ⅱ(3g,16mmol,1.0eq)，NaOH(0.72g,18mmol,1.1eq)，然后在0℃条件下逐滴加入f(0.8g,17mmol,1.05eq)，然后反应液在0℃条件下搅拌1小时。LCMS检测显示原料基本反应完毕，有一个主要的新峰。将反应液倒入30毫升水中，分液，水相用50毫升乙酸乙酯萃取一次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到g(3.0g,90％收率)(无色的油)。(1) Add Ⅱ(3g, 16mmol, 1.0eq), NaOH (0.72g, 18mmol, 1.1eq) to 30ml of DMF in sequence, then add f(0.8g, 17mmol, 1.05eq) dropwise at 0℃ ), and then the reaction solution was stirred at 0°C for 1 hour. LCMS detection showed that the raw materials had basically reacted and there was a major new peak. The reaction liquid was poured into 30 ml of water, and the liquid was separated. The aqueous phase was extracted once with 50 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried, and separated by column chromatography to obtain g (3.0 g, 90% yield) (colorless oil).
(2)在30毫升的THF中加入g(2.8g,13mmol,1.0eq)，然后在-78℃条件下缓慢加入n-BuLi(6.42ml,2.5M,16mmol,1.2eq)，然后反应液在-78℃条件下搅拌0.5小时后缓慢通入CO
2，通入10min后反应液缓慢升到室温。LCMS检测到产品。往反应液中倒入20毫升水，分液，水相用30毫升乙酸乙酯萃取一次，水相用浓盐酸逐渐调到pH＝4-5，过滤，干燥得到h(2.7g,85％收率)(白色固体)。
(2) Add 30g (2.8g, 13mmol, 1.0eq) to 30ml of THF, then slowly add n-BuLi (6.42ml, 2.5M, 16mmol, 1.2eq) at -78°C, then the reaction solution is After stirring at -78°C for 0.5 hours, CO 2 was slowly introduced, and after 10 minutes, the reaction solution was slowly raised to room temperature. LCMS detected the product. Pour 20 ml of water into the reaction solution and separate the layers. The aqueous phase is extracted once with 30 ml of ethyl acetate. The aqueous phase is gradually adjusted to pH=4-5 with concentrated hydrochloric acid, filtered and dried to obtain h (2.7 g, 85% yield). Rate) (white solid).
(3)在30毫升的吡啶中依次加入h(2.7g,11mmol,1.0eq)，d(1.66g,16.8mmol,1.5eq),DMAP(0.13g,1.1mmol,0.1eq)。然后在0℃条件下缓慢加入SOCl
2(2.0g,16.8mmol,1.5eq)，然后反应液在室温条件下搅拌3小时。LCMS检测到产品。浓缩除掉吡啶后往反应液倒入30毫升水，分液，水相用30毫升乙酸乙酯萃取三次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到化合物1-127(2.3g,63％收率)(白色固体)。
(3) To 30 ml of pyridine, add h (2.7 g, 11 mmol, 1.0 eq), d (1.66 g, 16.8 mmol, 1.5 eq), and DMAP (0.13 g, 1.1 mmol, 0.1 eq). Then, SOCl 2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0°C, and then the reaction solution was stirred at room temperature for 3 hours. LCMS detected the product. After removing pyridine by concentration, pour 30 ml of water into the reaction solution to separate the liquid. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried and separated by column chromatography Compound 1-127 (2.3 g, 63% yield) (white solid).
8、化合物1-132的合成8. Synthesis of Compound 1-132
(1)在30毫升的DMF中依次加入Ⅱ(3g,16mmol,1.0eq)，NaOH(0.72g,18mmol,1.1eq)，然后在0℃条件下逐滴加入i(17ml,1M in THE,17mmol,1.05eq)，然后反应液在0℃条件下搅拌1小时。LCMS检测显示原料基本反应完毕，有一个主要的新峰。将反应液倒入30毫升水中，分液，水相用50毫升乙酸乙酯萃取一次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到j(3.1g,92％收率)(无色的油)。(1) Add Ⅱ(3g, 16mmol, 1.0eq), NaOH (0.72g, 18mmol, 1.1eq) to 30ml of DMF in sequence, then add i(17ml, 1M in THE, 17mmol) dropwise at 0℃ , 1.05eq), and then the reaction solution was stirred at 0°C for 1 hour. LCMS detection showed that the raw materials had basically reacted and there was a major new peak. The reaction solution was poured into 30 ml of water, and the layers were separated. The aqueous phase was extracted once with 50 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried, and separated by column chromatography to obtain j (3.1 g, 92% yield) (colorless oil).
(2)在30毫升的THF中加入j(2.75g,13mmol,1.0eq)，然后在-78℃条件下缓慢加入n-BuLi(6.42ml,2.5M,16mmol,1.2eq)，然后反应液在-78℃条件下搅拌0.5小时后缓慢通入CO
2，通入10min后反应液缓慢升到室温。LCMS检测到产品。往反应液中倒入20毫升水，分液，水相用30毫升乙酸乙酯萃取一次，水相用浓盐酸逐渐调到pH＝4-5，过滤，干燥得到k(2.5g,80％收率)(白色固体)。
(2) Add j (2.75g, 13mmol, 1.0eq) to 30ml of THF, then slowly add n-BuLi (6.42ml, 2.5M, 16mmol, 1.2eq) at -78°C, and then After stirring at -78°C for 0.5 hours, CO 2 was slowly introduced, and after 10 minutes, the reaction solution was slowly raised to room temperature. LCMS detected the product. Pour 20 ml of water into the reaction liquid, separate the liquid, extract the aqueous phase once with 30 ml of ethyl acetate, adjust the aqueous phase gradually to pH=4-5 with concentrated hydrochloric acid, filter, and dry to obtain k (2.5 g, 80% yield) Rate) (white solid).
(3)在30毫升的吡啶中依次加入k(2.5g,11mmol,1.0eq)，d(1.66g,16.8mmol,1.5eq),DMAP(0.13g,1.1mmol,0.1eq)。然后在0℃条件下缓慢加入SOCl
2(2.0g,16.8mmol,1.5eq)，然后反应液在室温条件下搅拌3小时。LCMS检测到产品。浓缩除掉吡啶后往反应液倒入30毫升水，分液，水相用30毫升乙酸乙酯萃取三次，有机相用饱和食盐水(50ml)洗三次，干燥，旋干，柱层析分离得到化合物1-132(2.1g,61％收率)(白色固体)。
(3) In 30 ml of pyridine, add k (2.5 g, 11 mmol, 1.0 eq), d (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq). Then, SOCl 2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0°C, and then the reaction solution was stirred at room temperature for 3 hours. LCMS detected the product. After removing pyridine by concentration, pour 30 ml of water into the reaction solution to separate the liquid. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the organic phase was washed three times with saturated brine (50 ml), dried, spin-dried and separated by column chromatography. Compound 1-132 (2.1 g, 61% yield) (white solid).
9、化合物1-8(R构型)的合成9. Synthesis of Compounds 1-8 (R configuration)
参照上述化合物1-5的制备方法制得化合物1-8，然后将化合物1-8(0.5g,98％purity)通过手性HPLC(Column：CHIRALPAK IG；Column Size：3cm x 25cm,5um；Injection：3.0ml；Mobile phase：Hex(0.2％FA)：IPA＝50：50；Flow rate：28ml/min；Wavelength:UV 254nm；Temperature:25℃；Sample solution：70mg/ml in EtOH/DCM；Run time＝60mins)拆分之后浓缩，经单晶衍射确定得到白色固体1-8(R构型)(0.16g,Rt＝10.51min,100％ee,纯度为98％)和1-8(S构型)(0.13g,Rt＝30.81min,99.8％ee,纯度为96％)。Compound 1-8 was prepared according to the preparation method of compound 1-5 above, and then compound 1-8 (0.5g, 98% purity) was passed through chiral HPLC (Column: CHIRALPAK IG; Column Size: 3cm x 25cm, 5um; Injection : 3.0ml; Mobile phase: Hex (0.2% FA): IPA = 50: 50; Flow: 28ml/min; Wavelength: UV 254nm; Temperature: 25°C; Sample solution: 70mg/ml in EtOH/DCM; Run time = 60mins) after resolution and concentration, it was confirmed by single crystal diffraction to obtain white solids 1-8 (R configuration) (0.16g, Rt = 10.51min, 100%ee, purity 98%) and 1-8 (S configuration ) (0.13g, Rt=30.81min, 99.8%ee, purity 96%).
生物活性评价：Evaluation of biological activity:
植物破坏(即生长控制率)的活性级别标准如下：The standard of activity level of plant destruction (ie growth control rate) is as follows:
5级：生长控制率在85％以上；Level 5: The growth control rate is above 85%;
4级：生长控制率大于等于60％且小于85％；Level 4: The growth control rate is greater than or equal to 60% and less than 85%;
3级：生长控制率大于等于40％且小于60％；Level 3: Growth control rate is greater than or equal to 40% and less than 60%;
2级：生长控制率大于等于20％且小于40％；Level 2: The growth control rate is greater than or equal to 20% and less than 40%;
1级：生长控制率大于等于5％且小于20％；Level 1: The growth control rate is greater than or equal to 5% and less than 20%;
0级：生长控制率小于5％。Level 0: The growth control rate is less than 5%.
以上生长控制率为鲜重控制率。The above growth control rate is the fresh weight control rate.
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、菵草、硬草、蜡烛草、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、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)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)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，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克/公顷，重复三次，取平均值。代表性数据列于表2。Post-emergence test experiment: the monocotyledonous and dicotyledonous weed seeds (Artemisia sophora, shepherd's purse, hemp seed, sorrel, hellebore, wheat family, sorrel, maidenhair, smilax, hard grass, candle grass , Brome, knotweed, pheasant, amaranth, quinoa, dayflower, endive, field bindweed, eryngium, nightshade, amaranth, horsetail, barnyard grass, bristlegrass, golden bristlegrass, Thousands of gold, rhododendron, wild kindness, fireflies, monkshood, broken rice sedge, heterotypic sedge, drift grass, purslane, cocklebur, morning glory) and main crop seeds (wheat, corn, rice, soybean , Cotton, rapeseed, millet, sorghum, potato, sesame, castor) placed in a plastic pot filled with soil, and then covered with 0.5-2 cm soil to grow in a good greenhouse environment, 2 weeks after planting -Treat the test plants at the 3-leaf stage, dissolve the compound of the present invention with acetone separately, then add Tween 80, use 1.5 liters/hectare emulsifiable concentrate of methyl oleate as a synergist, and dilute to a certain concentration with a certain amount of water The solution was sprayed onto the plants with a spray tower. Cultivate in the greenhouse for 3 weeks after application. After 3 weeks, the experimental effects of weeds were counted. The amount of the compound used was 500,250,125,60,15 g/ha, repeated three times, and the average value was taken. Representative data are listed in Table 2.
表2.苗后杂草试验Table 2. Post-emergence weed test
注：对照化合物A：
N表示部分数据缺失。
Note: Control Compound A: N means some data is missing.
表3.苗后杂草试验Table 3. Post-emergence weed test
| 化合物序号Compound number | 稗草Barnyard grass | 苘麻Velvetleaf | 马唐Matang | 狗尾草Bristlegrass | 剂量(g a.i./ha)Dosage (g.a.i./ha) |
| 1-11-1 | NN | 44 | 22 | 22 | 120120 |
| 1-11-1 | 22 | 22 | 11 | 11 | 6060 |
| 1-11-1 | 22 | NN | 11 | 11 | 3030 |
| 1-11-1 | 11 | NN | 00 | 00 | 1515 |
| 1-11-1 | 00 | NN | 00 | 00 | 7.57.5 |
| 1-2(R构型)1-2(R configuration) | 44 | NN | 44 | 33 | 6060 |
| 1-2(R构型)1-2(R configuration) | 33 | NN | 33 | 33 | 3030 |
| 1-2(R构型)1-2(R configuration) | 11 | NN | 11 | 22 | 1515 |
| 1-2(R构型)1-2(R configuration) | 00 | NN | 00 | 00 | 7.57.5 |
| 1-21-2 | 33 | 44 | 33 | 33 | 6060 |
| 1-41-4 | NN | 55 | 55 | 55 | 6060 |
| 1-5(R构型)1-5(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 1-5(R构型)1-5(R configuration) | 55 | NN | 55 | 55 | 3030 |
| 1-5(R构型)1-5(R configuration) | 55 | NN | 55 | 55 | 1515 |
| 1-5(R构型)1-5(R configuration) | 55 | NN | 44 | 44 | 7.57.5 |
| 1-5(R构型)1-5(R configuration) | 44 | NN | 33 | 33 | 3.753.75 |
| 1-51-5 | 55 | 55 | 55 | 55 | 6060 |
| 1-8(R构型)1-8(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 1-8(R构型)1-8(R configuration) | 55 | NN | 55 | 55 | 3030 |
| 1-8(R构型)1-8(R configuration) | 55 | NN | 55 | 55 | 1515 |
| 1-8(R构型)1-8(R configuration) | 55 | NN | 55 | 44 | 7.57.5 |
| 1-8(R构型)1-8(R configuration) | 55 | NN | 44 | 22 | 3.753.75 |
| 1-81-8 | 55 | 55 | 55 | 55 | 6060 |
| 1-14(R构型)1-14(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 1-14(R构型)1-14(R configuration) | 55 | NN | 55 | 55 | 3030 |
| 1-14(R构型)1-14(R configuration) | 55 | NN | 55 | 44 | 1515 |
| 1-14(R构型)1-14(R configuration) | 55 | NN | 44 | 44 | 7.57.5 |
| 1-141-14 | NN | 55 | 55 | 55 | 6060 |
| 1-171-17 | NN | 55 | 55 | 55 | 6060 |
| 1-201-20 | NN | 55 | 55 | 55 | 6060 |
| 1-521-52 | NN | 55 | 55 | 55 | 6060 |
| 1-57(R构型)1-57(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 1-82(R构型)1-82(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 1-392(R构型)1-392(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-395(R构型)1-395(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-397(R构型)1-397 (R configuration) | 55 | NN | 55 | 55 | 125125 |
| 1-398(R构型)1-398(R configuration) | 55 | NN | 55 | 55 | 250250 |
| 1-401(R构型)1-401(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-402(R构型)1-402(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-403(R构型)1-403 (R configuration) | 55 | NN | 55 | 55 | 6060 |
| 1-404(R构型)1-404 (R configuration) | 55 | NN | 55 | 55 | 6060 |
| 1-405(R构型)1-405(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 1-411(R构型)1-411(R configuration) | 55 | NN | 55 | 55 | 250250 |
| 1-412(R构型)1-412(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-413(R构型)1-413 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-414(R构型)1-414 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-427(R构型)1-427(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-428(R构型)1-428 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-429(R构型)1-429 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-430(R构型)1-430 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-431(R构型)1-431 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-432(R构型)1-432 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-441(R构型)1-441(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-443(R构型)1-443(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-444(R构型)1-444(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-446(R构型)1-446(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-447(R构型)1-447(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-448(R构型)1-448(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-523(R构型)1-523 (R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-525(R构型)1-525(R configuration) | 55 | NN | 55 | 55 | 500500 |
| 1-552(R构型)1-552 (R configuration) | 55 | NN | 55 | 55 | 125125 |
| 1-563(R构型)1-563 (R configuration) | 55 | NN | NN | NN | 125125 |
| 1-617(R构型)1-617(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 2-8(R构型)2-8(R configuration) | 55 | NN | 55 | 55 | 250250 |
| 3-43-4 | 55 | NN | 55 | 55 | 250250 |
| 3-5(R构型)3-5(R configuration) | 55 | NN | 55 | 55 | 120120 |
| 3-8(R构型)3-8(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 3-11(R构型)3-11(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 3-14(R构型)3-14(R configuration) | 55 | NN | 55 | 55 | 6060 |
| 3-17(R构型)3-17(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 3-20(R构型)3-20(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 3-52(R构型)3-52(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 3-543-54 | 55 | NN | 55 | 55 | 250250 |
| 3-57(R构型)3-57(R configuration) | 55 | NN | 55 | 55 | 125125 |
| 6-8(R构型)6-8(R configuration) | 55 | NN | 55 | 55 | 250250 |
| 对照化合物AControl Compound A | NN | 33 | 11 | 11 | 120120 |
经过测试发现本发明通式化合物中基团Y由甲基变成乙基或C3-C8烷基时，其杀草活性和杀草谱明显变好。尤其是低剂量时化合物1-4比化合物1-1、化合物1-5比化合物1-2在主要禾本科杂草(如水稻田主要禾本科杂草稗草、千金子或马唐)上活性高2倍以上，化合物1-8比化合物1-2高的更多，而当碳数超过8时，其活性又明显下降，而通式中其他基团中碳原子数量变化对活性并无明显影响。After testing, it is found that when the group Y in the compound of the present invention changes from methyl to ethyl or C3-C8 alkyl, its herbicidal activity and herbicidal spectrum are significantly improved. Especially at low doses, compound 1-4 is more active than compound 1-1 and compound 1-5 than compound 1-2 on major grass weeds (such as rice field major grass weed barnyardgrass, Qianjin or horse tang). More than 2 times, compound 1-8 is much higher than compound 1-2, and when the carbon number exceeds 8, its activity decreases significantly, but the change in the number of carbon atoms in other groups in the formula has no significant effect on activity .
对比实验：Comparative Experiment:
表4.对照实验安全性测试结果(对水稻产生10％药害的平均计量除以对稗草90％防效的平均计量为水稻和稗草间的除草剂选择指数，是重要的评价稻田除草剂安全性的指标。除草剂选择指数小于2时风险较高，不具备商业化价值。)Table 4. Safety test results of control experiments (the average dose of 10% phytotoxicity to rice divided by the average dose of 90% control effect to barnyard grass is the herbicide selection index between rice and barnyard grass, which is an important evaluation of weeding in rice fields An indicator of the safety of pesticides. When the herbicide selection index is less than 2, the risk is higher and it has no commercial value.)
| 化合物序号Compound number | 籼稻(黄华占)Indica rice (Huang Huazhan) | 粳稻(淮稻5号)Japonica rice (Huaidao No. 5) | 计量Measurement | 水稻和稗草的选择指数Selection index of rice and barnyard grass |
| 1-51-5 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-61-6 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-71-7 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-81-8 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-91-9 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-131-13 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-141-14 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-201-20 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-521-52 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-571-57 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-821-82 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 1-1341-134 | 00 | 00 | 250g a.i./ha250g a.i./ha | ＞5＞5 |
| 对照化合物BControl Compound B | 44 | 33 | 250g a.i./ha250g a.i./ha | 0.80.8 |
| 对照化合物BControl Compound B | 33 | 33 | 125g a.i./ha125g.a.i./ha | 0.80.8 |
| 对照化合物CControl Compound C | 55 | 44 | 125g a.i./ha125g.a.i./ha | 1.11.1 |
| 对照化合物DControl Compound D | 55 | 55 | 60g a.i./ha60g.a.i./ha | 11 |
注：对照化合物B：
对照化合物C：
Note: Control Compound B: Control Compound C:
对照化合物D：
Control Compound D:
由此表4可知，本发明化合物对水稻有极高的安全性和选择性，而对照化合物对水稻不安全，不管对于籼稻还是粳稻都产生了不可接受的药害。It can be seen from Table 4 that the compound of the present invention has extremely high safety and selectivity for rice, while the control compound is not safe for rice, and produces unacceptable phytotoxicity for indica rice or japonica rice.
综上可见，本发明化合物对水稻非常安全，选择指数远大于2，能够高效的防除稗草、马唐、狗尾草等禾本科杂草以及多种阔叶杂草，是水稻田的理想除草剂。In summary, the compound of the present invention is very safe for rice, and its selection index is much greater than 2. It can effectively control grass weeds such as barnyard grass, crabgrass, foxtail and other broad-leaved weeds, and is an ideal herbicide for rice fields.
苗后测试实验：播种3-4周后在直播水稻龙洋16品种1.5-2叶期、杂草4-5叶期处理测试植物。施药后在温室中培养25天，25天后统计杂草的实验效果，测试结果参见表5-6。Post-emergence test experiment: 3-4 weeks after sowing, the test plants were treated at the 1.5-2 leaf stage and the 4-5 leaf stage of the weeds of the 16 varieties of Longyang direct seeding rice. Cultivate in the greenhouse for 25 days after application. After 25 days, the experimental effects of weeds are counted. For test results, see Table 5-6.
表5.R构型化合物活性对照实验结果(抑制率％)Table 5. Results of control experiments on the activity of R-configuration compounds (inhibition rate %)
表6.R构型化合物活性对照实验结果(抑制率％)Table 6. Results of control experiments on the activity of R-configuration compounds (inhibition rate %)
龙洋16是中国东北重要的长粒香米的栽培品种代表，长粒香米对除草剂较为敏感，尤其是HPPD类的硝磺草酮，双环磺草酮等品种，都容易出现药害。令人意料之外的是，1-8(R构型)对水稻(龙洋16)有更高的安全性，并且对关键杂草千金子有更好的活性。而S体对水稻不安全，即作物药害重，而对关键杂草活性更低，甚至低剂量下没有活性。与我们熟知的芳氧苯氧丙酸类除草剂、苯氧丙酸类除草剂有效体活性高，药害重，无效体几乎没有活性的构效关系不一致。Longyang 16 is a representative of important long-grain rice varieties in Northeast China. Long-grain rice is sensitive to herbicides, especially HPPD-type mesotrione and bicyclosulone, which are prone to phytotoxicity. Surprisingly, 1-8 (R configuration) is more safe for rice (Longyang 16) and has better activity against the key weed, Qianjin. The S body is not safe for rice, that is, the crop is seriously toxic to crops, but it is less active against key weeds, and even inactive at low doses. It is inconsistent with the well-known aryloxyphenoxypropionic acid herbicides and phenoxypropionic acid herbicides. The effective body activity is high, the phytotoxicity is heavy, and the invalid body has almost no activity. The structure-activity relationship is inconsistent.
苗前测试实验：Pre-emergence test experiment:
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，4周后观察实验结果，发现本发明的药剂多数在250克/公顷计量 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、油菜有良好的选择性。Place monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet, sorghum) in plastic pots filled with soil, and then cover 0.5-2 cm of soil, respectively. 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 4 weeks of cultivation in the greenhouse after application, the experimental results were observed after 4 weeks, and it was found that most of the agents of the present invention are excellent at a dosage of 250 g/ha, especially for weeds such as barnyard grass, horse tang, velvetleaf, and many compounds It has good selectivity to corn, wheat, rice, soybean and rape.
通过实验我们发现本发明所述化合物普遍具有较好的杂草防效，尤其对于玉米田、水稻田、小麦田广泛发生的杂草稗草、马唐、狗尾草等主要禾本科杂草以及苘麻、蔊菜、鬼针草等主要的阔叶杂草有良好的效果，具备良好的商业价值。尤其是我们注意到对于ALS抑制剂有抗性的蔊菜、播娘蒿、荠菜、麦家公、猪殃殃、繁缕等阔叶杂草有极高的活性。Through experiments, we found that the compounds of the present invention generally have better weed control effects, especially for weeds such as barnyardgrass, horsetail, foxtail, etc., and velvetleaf, which occur widely in corn fields, rice fields, and wheat fields. , The main broad-leaved weeds such as radix caulis, needle needle grass, etc. have good effects and have good commercial value. In particular, we have noticed that the broadleaf weeds that are resistant to ALS inhibitors, such as Chestnut, Sophora vulgare, Shepherd's purse, Maijiagong, Swamp, and Stellaria, have extremely high activity.
移栽水稻安全性评价与水田杂草防效评价：Evaluation of the safety of transplanted rice and the evaluation of weed control effectiveness in paddy fields:
在1/1,000,000公顷罐中装入水田土壤后，播种稗草、萤蔺、狼把草、野慈姑、鸭舌草、千金子的种子，在其上轻轻地覆盖土。其后以蓄水深0.5-1厘米的状态静置于温室内，第二天或者2天后植入野慈姑的块茎。其后保持蓄水深3-4厘米，在稗草、萤蔺、狼把草、鸭舌草、千金子达到0.5叶，野慈姑达到初生叶期的时间点，将按照通常的制剂方法调制本发明化合物而成的可湿性粉剂或者悬浮剂的水稀释液，用吸液管进行均匀的滴下处理以达到规定的有效成分量。After filling the paddy field soil in 1/1,000,000 hectares of pots, sow the seeds of barnyard grass, fireflies, wolfgrass, wild kindergarten, rhododendron, and thousand gold, and gently cover the soil with it. After that, it was placed in a greenhouse with a water storage depth of 0.5-1 cm, and the tubers of Yecigu were implanted the next day or 2 days later. Afterwards, the water storage depth is 3-4 cm. When the barnyard grass, firefly, wolfgrass, rhododendron, and sylvestris reach 0.5 leaves, the time when the wild Cigu reaches the primary leaf stage will be prepared according to the usual preparation method. The water dilution of the wettable powder or suspending agent made of the compound of the invention is uniformly dropped with a pipette to achieve the prescribed amount of active ingredients.
另外，在1/1,000,000公顷罐中装入水田土壤后，进行平整，使蓄水深3-4厘米，第二天以移栽深度3厘米来移植3叶期的水稻(粳稻/籼稻)。移植后第5天与上述同样地处理本发明化合物。In addition, after filling the paddy field soil in a 1/1,000,000 hectare pot, it was leveled so that the water storage depth was 3-4 cm, and the 3-leaf rice (Japonica/Indica) was transplanted at the transplant depth of 3 cm the next day. On the fifth day after transplantation, the compound of the present invention was treated in the same manner as described above.
分别用肉眼观察药剂处理后第14天稗草、萤蔺、狼把草、千金子、野慈姑及鸭舌草的生育状态，药剂处理后第21天水稻的生育状态，以上述0-5级的活性标准级别评价除草效果，很多化合物表现出了优异的活性和选择性。Observe the growth status of barnyardgrass, firefly, leptia sylvestris, Qianjin, Yecigu, and Agrithoprus by the naked eye on the 14th day after the chemical treatment. The growth status of rice on the 21st day after the chemical treatment is 0-5 The activity standard grade evaluates the herbicidal effect, and many compounds show excellent activity and selectivity.
表7.实验活性和安全性测试结果(剂量为125g a.i./ha)Table 7. Experimental activity and safety test results (dose 125g a.i./ha)
| 化合物序号Compound number | 稗草Barnyard grass | 萤蔺Firefly | 鸭舌草Zantedeschia | 水稻Rice |
| 1-41-4 | 55 | 55 | 55 | 00 |
| 1-51-5 | 55 | 55 | 55 | 00 |
| 1-61-6 | 55 | 55 | 55 | 00 |
| 1-81-8 | 55 | 55 | 55 | 00 |
| 1-111-11 | 55 | 55 | 55 | 00 |
| 1-141-14 | 55 | 55 | 55 | 00 |
| 1-571-57 | 55 | 55 | 55 | 00 |
| 1-761-76 | 55 | 55 | 55 | 00 |
表8.化合物除草效果(本申请化合物剂量为60g a.i./ha)Table 8. Herbicidal effect of the compound (the compound dosage of this application is 60g a.i./ha)
注：稗草、萤蔺、狼把草、野慈姑及鸭舌草种子均采集自中国黑龙江，经过检测对常规剂量的吡嘧磺隆、五氟磺草胺有抗药性。Note: The seeds of barnyard grass, rushes, wolfgrass, wild Cigu and rhododendron were collected from Heilongjiang, China, and tested to be resistant to conventional dosages of pyrazosulfuron-methyl and penoxsulam.
由本实验可以看出，本发明化合物对生产中面临严重挑战的抗ALS抑制作用机理的杂草有优秀的活性，能够解决日益严重的抗性问题。It can be seen from this experiment that the compounds of the present invention have excellent activity against weeds that are facing a serious challenge in the mechanism of anti-ALS inhibition, and can solve the increasingly serious problem of resistance.
另外，本发明还涉及一种包含除草有效量的有效成分(i)(如通式I所示的化合物)与有效成分(ii)的除草组合物，以及还可包括一种或多种安全剂和/或农业化学上可接受的制剂助剂等。In addition, the present invention also relates to a herbicidal composition containing a herbicidally effective amount of an active ingredient (i) (a compound represented by Formula I) and an active ingredient (ii), and may also include one or more safeners And/or agrochemically acceptable formulation aids, etc.
其中，采用茎叶处理法测定上述部分(i)与(ii)的混配对杂草的实际防效，即待杂草处于3-4叶期，手动喷雾器，兑水量30公斤/667m
2，采用茎叶喷雾均匀喷雾。处理后20天调查，并用Gowing法计算各处理混合组合的理论鲜重抑制率(E0＝X+Y-X*Y/100)，然后与实测抑制率(E)相比较，评价二者混用对杂草的联合作用类型，当E-E0值大于10％为增效作用、小于-10％为拮抗作用、在-10％～10％之间为加成作用。并根据实际防效和除草剂特点、配方的平衡性等因素确定最佳配比。式中X为活性成分(i)用量为P时的鲜重抑制率；Y为活性成分(ii)用量为Q时的鲜重抑制率。统计结果见下表9-11。
Among them, the stem and leaf treatment method was used to determine the actual control effect of the mixed weeds in the above parts (i) and (ii), that is, when the weeds were in the 3-4 leaf stage, a manual sprayer with a water content of 30 kg/667m 2 was used Spray the stem and leaves evenly. Survey 20 days after treatment, and use Gowing method to calculate the theoretical fresh weight suppression rate (E0=X+YX*Y/100) of each combination of treatments, and then compare it with the measured suppression rate (E) to evaluate the mixed use of the two for weeds When the E-E0 value is greater than 10%, it is synergistic, less than -10% is antagonistic, and between -10% and 10% is additive. And according to the actual control effect and herbicide characteristics, the balance of the formula and other factors to determine the best ratio. In the formula, X is the fresh weight suppression rate when the amount of the active ingredient (i) is P; Y is the fresh weight suppression rate when the amount of the active ingredient (ii) is Q. The statistical results are shown in Table 9-11 below.
表9.(i)与(ii)混配对杂草的实际防效及联合作用评价(Gowing法)Table 9. (i) and (ii) mixed weeds' actual control effectiveness and joint action evaluation (Gowing method)
注：亩是中国的土地面积单位，十五亩等于一公顷，即1亩(mu)＝1/15公顷(ha)。Note: Mu is the unit of land area in China. Fifteen mu equals one hectare, that is, 1 mu (mu) = 1/15 hectare (ha).
表10.(i)与(ii)混配对杂草的实际防效及联合作用评价(Gowing法)Table 10. (i) and (ii) mixed weeds' actual control effectiveness and joint action evaluation (Gowing method)
注：亩是中国的土地面积单位，十五亩等于一公顷，即1亩(mu)＝1/15公顷(ha)。Note: Mu is the unit of land area in China. Fifteen mu equals one hectare, that is, 1 mu (mu) = 1/15 hectare (ha).
表11.(i)与(ii)混配对杂草的实际防效及联合作用评价(Gowing法)Table 11. (i) and (ii) mixed weeds' actual control effectiveness and joint action evaluation (Gowing method)
注：亩是中国的土地面积单位，十五亩等于一公顷，即1亩(mu)＝1/15公顷(ha)。Note: Mu is the unit of land area in China. Fifteen mu equals one hectare, that is, 1 mu (mu) = 1/15 hectare (ha).
另外，表B1列出了其他组分(i)与组分(ii)的特定组合，进一步说明了本发明的组合物。“组分(i)/化合物序号”列中的化合物标识在索引表A1中。表B1的第二列列出了特定组分(ii)化合物(例如第一行中的“吡嘧磺隆”)。表B1的其余行将被类似地构造。In addition, Table B1 lists specific combinations of other components (i) and components (ii), further illustrating the composition of the present invention. The compounds in the column of "component (i)/compound number" are identified in the index table A1. The second column of Table B1 lists the specific component (ii) compounds (for example "pyrimsulfuron" in the first row). The remaining rows of Table B1 will be constructed similarly.
表B1组合物各成分列表Table B1 List of ingredients in the composition
| 组分(i)/化合物序号Component (i)/Compound No. | 组分(ii)Component (ii) |
| 1-31-3 | 吡嘧磺隆Pyrasulfuron |
| 1-31-3 | 五氟磺草胺Penoxsulam |
| 1-31-3 | 双草醚Bispyribac |
| 1-31-3 | 嘧草醚Miclofen |
| 1-31-3 | 嗪吡嘧磺隆Azimesulfuron |
| 1-31-3 | 丙嗪嘧磺隆Promethazine |
| 1-31-3 | 氟酮磺草胺Fluoxsulam |
| 1-31-3 | 氰氟草酯Fenfluroxim |
| 1-31-3 | 噁唑酰草胺Oxachlor |
| 1-31-3 | 二氯喹啉酸Quinclorac |
| 1-31-3 | 2甲4氯2 A 4 Chlorine |
| 1-31-3 | 2,4-D2,4-D |
| 1-31-3 | 2,4-D丁酸2,4-D butyric acid |
| 1-31-3 | 氯氟吡氧乙酸Chlorofluoropyroxyacetic acid |
| 1-31-3 | 氯氟吡啶酯Chlorofluoropyridinate |
| 1-31-3 | 2甲4氯丁酸2 A 4 chlorobutyric acid |
| 1-31-3 | 麦草畏Dicamba |
| 1-31-3 | 二氯喹啉草酮Diclofenac |
| 1-31-3 | 二氯吡啶酸Diclopic acid |
| 1-31-3 | 三氯吡氧乙酸Triclofenac |
| 1-31-3 | 二甲戊灵Pendimethalin |
| 1-31-3 | 仲丁灵Zhong Dingling |
| 1-31-3 | 禾草丹Hedan |
| 1-31-3 | 禾草敌Grass foe |
| 1-31-3 | ***磺草酮Trimetrione |
| 1-31-3 | 双唑草酮Alazodone |
| 1-31-3 | 环吡氟草酮Ciprofloxacin |
| 1-31-3 | 硝磺草酮Mesotrione |
| 1-31-3 | 双环磺草酮Bicyclosulfonone |
| 1-31-3 | 呋喃磺草酮Furosemide |
| 1-31-3 | 吡氟酰草胺Pyraflufenacil |
| 1-31-3 | 氟咯草酮Fluroxypyr |
| 1-31-3 | 氟丁酰草胺Flubutachlor |
| 1-31-3 | 唑草酮Azaconone |
| 1-31-3 | 双唑草腈Azaprofen |
| 1-31-3 | 噁草酮Oxadiazon |
| 1-31-3 | 丙炔噁草酮Propynoxazone |
| 1-31-3 | 乙氧氟草醚Ethoxyflufen |
| 1-31-3 | 环戊噁草酮Cyclopentachlor |
| 1-31-3 | 丁草胺Butachlor |
| 1-31-3 | 丙草胺Alachlor |
| 1-31-3 | 苯噻酰草胺Fenacetamide |
| 1-31-3 | 莎稗膦Sarcosine |
| 1-31-3 | 四唑酰草胺Tetrazolamide |
| 1-31-3 | 异丙甲草胺Metolachlor |
| 1-31-3 | 哌草磷Pipemid |
| 1-31-3 | 砜吡草唑Sulfamethoxazole |
| 1-31-3 | 西草净Xi Cao Jing |
| 1-31-3 | 扑草净Promethazine |
| 1-31-3 | 胺唑草酮Azachlor |
| 1-31-3 | 异丙隆Isoprofen |
| 1-31-3 | 除草定Herbicide |
| 1-31-3 | 哒草特Dacaote |
| 1-31-3 | 绿麦隆Green myron |
| 1-31-3 | 灭草松Bentazone |
| 1-31-3 | 敌稗Diarrhea |
| 1-31-3 | 嗪草酮Chlorpyrifos |
| 1-31-3 | 莠去津Atrazine |
| 1-31-3 | 溴苯腈Bromoxynil |
| 1-31-3 | 辛酰溴苯腈Octanoyl bromoxynil |
| 1-31-3 | 特丁津Tedinjin |
| 1-31-3 | 异噁草松Clomazone |
| 1-31-3 | 噁嗪草酮Oxachlor |
| 1-31-3 | 环庚草醚Cycloheptafen |
| 1-31-3 | 茚草酮Indanone |
表B2如以上表B1相同构造，除了“组分(i)/化合物序号”列标题下面的条目被下文所示的相应“组分(i)/化合物序号”列条目替代。“组分(i)/化合物序号”列中的化合物标识在索引表A1-A152中。因此，例如，在表B2中，“组分(i)/化合物序号”列标题下面的条目全都叙述“1-5”(即，索引表A1中所标识的化合物1-5)，并且表B2中的列标题下面的第一行具体披露了化合物1-5与“吡嘧磺隆”的混合物。表B3至B167类似地构造。Table B2 has the same structure as Table B1 above, except that the entry below the column heading of "Component (i)/Compound No." is replaced by the corresponding column entry of "Component (i)/Compound No." shown below. The compounds in the column of "component (i)/compound number" are identified in index tables A1-A152. So, for example, in Table B2, the entries under the column heading "Component (i)/Compound No." all describe "1-5" (ie, index compounds 1-5 identified in Table A1), and Table B2 The first row below the column heading in the detailed disclosure of a mixture of compounds 1-5 and "pyrisulfuron". Tables B3 to B167 are constructed similarly.
同时经过很多测试发现，本发明中的其他组分(i)与组分(ii)混配同样能够产生类似的除草效果。另外，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小麦、玉米、水稻、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。At the same time, after many tests, it was found that other components (i) and component (ii) in the present invention can also produce similar herbicidal effects. In addition, many of the compounds and compositions of the present invention have good selectivity to grass lawns such as Zoysia japonica, bermudagrass, tall fescue, bluegrass, ryegrass, seashore paspalum, and can control many key grasses Weeds and broad-leaved weeds. Tests on wheat, corn, rice, sugar cane, soybean, cotton, oil sunflower, potato, fruit tree, vegetable, etc. under different application methods also showed excellent selectivity and commercial value.
Claims (10)
- 一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其结构式如下：An N-(1,3,4-oxadiazol-2-yl) aryl formamide compound or its salt, the structural formula is as follows:
其中，X代表O、S、SO、SO 2或NR 1； Among them, X represents O, S, SO, SO 2 or NR 1 ;Y代表卤素，氰基，氰基烷基，羧基，硝基，N(R 2) 2，-烷基-N(R 2) 2，CON(R 2) 2，-烷基-CON(R 2) 2，-烷基-N(R 2) 3 +I -，羟基烷基，被氨基和羧基取代的烷基，OR 3，SR 3，-烷基-SOR 3，-烷基-OR 3，-烷基-SR 3，COR 3，COOR 3，-烷基-COR 4，-烷基-COOR 4，-烷基-OCOR 3，Si(R 3) 3，-烷基-O-Si(R 3) 3，-烷基-O-N＝C(R 3) 2，烷基，卤代烷基，未取代或被选自卤素、氰基、环烷基、烷基羰基、烷氧基羰基、烷氧基、烷硫基、烷基亚硫酰基、烷基磺酰基、三烷基硅基中的至少一个基团所取代的烯基、炔基，未取代或取代的环烷基、环烷基烷基，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； Y represents halogen, cyano, cyanoalkyl, carboxyl, nitro, N(R 2 ) 2 , -alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , -alkyl-CON(R 2 ) 2, - alkyl -N (R 2) 3 + I -, hydroxyalkyl, amino and carboxy substituted alkyl, OR 3, SR 3, - alkyl -SOR 3, - alkyl -OR 3, -Alkyl-SR 3 , COR 3 , COOR 3 , -alkyl-COR 4 , -alkyl-COOR 4 , -alkyl-OCOR 3 , Si(R 3 ) 3 , -alkyl-O-Si(R 3 ) 3 ,-alkyl-ON=C(R 3 ) 2 , alkyl, haloalkyl, unsubstituted or selected from halogen, cyano, cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxy , Alkylthio, alkylsulfinyl, alkylsulfonyl, trialkylsilyl substituted alkenyl, alkynyl, unsubstituted or substituted cycloalkyl, cycloalkylalkyl , Unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl;或者-X-Y代表未取代或取代的五元或六元杂环基或杂芳基，该环上除含有C原子和1-位上的N原子外，还含有0-3个以下原子或基团作为环的组成部分：O、N、NR 1、SO 2、C＝O； Or -XY represents an unsubstituted or substituted five-membered or six-membered heterocyclic group or heteroaryl group, in addition to the C atom and the N atom at the 1-position, the ring also contains 0 to 3 atoms or groups below As a component of the ring: O, N, NR 1 , SO 2 , C=O;Z代表氢，卤素，氰基，OR 4，-烷基-OR 4，-O-烷基-N(R 5) 2，-烷基-O-烷基-N(R 5) 2，N(R 5) 2，-烷基-(C＝O) m-N(R 5) 2，-NH-烷基-N(R 5) 2，不含或含有卤素的烷基、烯基、炔基、烷氧基羰基、烷氧基羰基烷基、烷基羰基、烷基羰基烷基、烷基羰基氧基烷基、烷硫基、烷基亚磺酰基、烷基磺酰基，未取代或取代的环烷基，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、杂环基羰基烷基、芳基羰基烷基、杂芳基羰基烷基、杂环基羰基氧基烷基、芳基羰基氧基烷基、杂芳基羰基氧基烷基； Z represents hydrogen, halogen, cyano, OR 4 , -alkyl-OR 4 , -O-alkyl-N(R 5 ) 2 , -alkyl-O-alkyl-N(R 5 ) 2 , N( R 5 ) 2 ,-alkyl-(C═O) m -N(R 5 ) 2 ,-NH-alkyl-N(R 5 ) 2 , alkyl, alkenyl, alkynyl groups that do not contain or contain halogen , Alkoxycarbonyl, alkoxycarbonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, unsubstituted or substituted Cycloalkyl, unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, heterocyclylcarbonylalkyl, arylcarbonylalkyl , Heteroarylcarbonylalkyl, heterocyclylcarbonyloxyalkyl, arylcarbonyloxyalkyl, heteroarylcarbonyloxyalkyl;M代表氢，OR 6，SR 6，COR 6，COOR 6，OCOR 6，CON(R 7) 2，N(R 7) 2，NR 8COOR 6，NR 8CON(R 7) 2，-烷基-R，不含或含有卤素的烷基、烯基、炔基、环烷基，以及未取代或取代的芳基烷基、杂芳基烷基； M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -alkyl -R, alkyl group, alkenyl group, alkynyl group, cycloalkyl group not containing or containing halogen, and unsubstituted or substituted arylalkyl group, heteroarylalkyl group;R代表不含或含有卤素的烯基、炔基、环烷基，CN，OR 11，OCOR 11，COOR 11，COR 11，-O-(C＝O)-O-R 11，OSO 2R 12，SO 2OR 11，-S(O) nR 12，N(R 13) 2，CON(R 13) 2，SO 2N(R 13) 2，NR 14COR 11，NR 14SO 2R 12，-O-(C＝O)-N(R 13) 2； R represents alkenyl, alkynyl, cycloalkyl without or containing halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)-OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O -(C＝O)-N(R 13 ) 2 ;R 4、R 6、R 11分别独立地代表氢、不含或含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、烷氧基烷基，以及未取代或取代的杂环基、杂环基烷基、杂环基氧基烷基、芳基、芳基烷基、芳基氧基烷基、杂芳基、杂芳基烷基、杂芳基氧基烷基； R 4 , R 6 , and R 11 independently represent hydrogen, an alkyl group containing no or halogen, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, alkoxyalkyl group, and Unsubstituted or substituted heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl, heteroaryl Oxyalkyl;R 3、R 12分别独立地代表不含或含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、环烯基、烷氧基烷基，以及未取代或取代的杂环基、杂环基烷基、芳基、芳基烷基、杂芳基、杂芳基烷基； R 3 and R 12 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, alkoxyalkyl, and unsubstituted or substituted Heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl;R 1、R 2、R 5、R 7、R 8、R 13、R 14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R 21) 2、CON(R 21) 2、OR 21、COR 21、CO 2R 21、COSR 21、OCOR 21、S(O) rR 22、烷基、卤代烷基、烯基、卤代烯基、炔基、卤代炔基、环烷基、环烯基、卤代环烷基、烷氧基烷基、环烷基烷基、芳基、芳基烷基、芳基氧基、芳基氧基烷基、芳基烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基烷基、杂芳基氧基、杂芳基氧基烷基、杂芳基烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基烷基、杂环基氧基、杂环基氧基烷基、杂环基烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR 21-烷基、杂芳基-NR 21-烷基、杂环基-NR 21-烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR 21、S(O) rR 22、N(R 21) 2、NR 21OR 21、COR 21、OCOR 21、SCOR 22、NR 21COR 21、NR 21SO 2R 22、CO 2R 21、COSR 21、CON(R 21) 2和烷氧基烷氧基羰基； R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , alkyl, haloalkyl, alkenyl, haloalkenyl , Alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryl Oxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyl Oxygen, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclyloxyalkyl, heterocyclylalkyloxy, heterocyclylcarbonyl , Heterocyclylsulfonyl, aryl-NR 21 -alkyl, heteroaryl-NR 21 -alkyl, heterocyclyl-NR 21 -alkyl, wherein the last 35 groups mentioned are each 0, 1 , 2 or 3 group substitutions selected from cyano, halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON (R 21 ) 2 and alkoxyalkoxycarbonyl;R 21分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基； R 21 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;R 22分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基； R 22 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkylalkyl;m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;当X代表S、SO时，Y不为甲基。When X represents S and SO, Y is not methyl. - 根据权利要求1所述的一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其特征在于，An N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or a salt thereof according to claim 1, whereinX代表O、S、SO、SO 2或NR 1； X represents O, S, SO, SO 2 or NR 1 ;Y代表卤素，氰基，氰基C1-C8烷基，羧基，硝基，N(R 2) 2，-(C1-C8)烷基-N(R 2) 2，CON(R 2) 2，-(C1-C8)烷基-CON(R 2) 2，-(C1-C8)烷基-N(R 2) 3 +I -，羟基C1-C8烷基，被氨基和羧基取代的C1-C8烷基，OR 3，SR 3，-(C1-C8)烷基-SOR 3，-(C1-C8)烷基-OR 3，-(C1-C8)烷基-SR 3，COR 3，COOR 3，-(C1-C8)烷基-COR 4，-(C1-C8)烷基-COOR 4，-(C1-C8)烷基-OCOR 3，Si(R 3) 3，-(C1-C8)烷基-O-Si(R 3) 3，-(C1-C8)烷基-O-N＝C(R 3) 2，C1-C8烷基，卤代C1-C8烷基，未取代或被选自卤素、氰基、C3-C8环烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷氧基、C1-C8烷硫基、C1-C8烷基亚硫酰基、C1-C8烷基磺酰基、三C1-C8烷基硅基中的至少一个基团所取代的C2-C8烯基、C2-C8炔基，未取代或被选自C1-C8烷基、卤素、苯基中的至少一个基团取代的C3-C8环烷基、C3-C8环烷基C1-C8烷基，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； Y represents halogen, cyano, cyano C1-C8 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C8)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C8) alkyl -CON (R 2) 2, - (C1-C8) alkyl -N (R 2) 3 + I -, hydroxy C1-C8 alkyl, substituted amino and carboxyl C1- C8 alkyl, OR 3 , SR 3 , -(C1-C8)alkyl-SOR 3 , -(C1-C8)alkyl-OR 3 , -(C1-C8)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C8)alkyl-COR 4 ,-(C1-C8)alkyl-COOR 4 ,-(C1-C8)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C8 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C8)alkyl-ON=C(R 3 ) 2 ,C1-C8 alkyl, halogenated C1-C8 alkyl, unsubstituted or selected From halogen, cyano, C3-C8 cycloalkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylsulfinyl , C1-C8 alkylsulfonyl, C2-C8 alkenyl, C2-C8 alkynyl substituted with at least one group of tri-C1-C8 alkylsilyl, unsubstituted or selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl substituted with at least one group of halogen, phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl;或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，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、苯氧基，以及含有或不含有卤素的烷基、烯基、炔基、环烷基、环烷基烷基、烷氧基、烷硫基、烷氧基烷基、烷硫基烷基、烷基羰基、烷氧基羰基、烷基亚硫酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基酰氧基中的至少一个基团所取代的
Or -XY represents unsubstituted or selected by halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or substituted by at least one group selected from halogen, alkyl, alkoxy Substituted phenyl, benzyl, phenoxy, and alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkoxyalkyl with or without halogen Substituted by at least one group of alkyl, alkylthioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylacyloxy of
Z代表氢，卤素，氰基，OR 4，-(C1-C8)烷基-OR 4，-O-(C1-C8)烷基-N(R 5) 2，-(C1-C8)烷基-O-(C1-C8)烷基-N(R 5) 2，N(R 5) 2，-(C1-C8)烷基-(C＝O) m-N(R 5) 2，-NH-(C1-C8)烷基-N(R 5) 2，不含或含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C1-C8烷氧基羰基、C1-C8烷氧基羰基C1-C8烷基、C1-C8烷基羰基、C1-C8烷基羰基C1-C8烷基、C1-C8烷基羰基氧基C1-C8烷基、C1-C8烷硫基、C1-C8烷基亚磺酰基、C1-C8烷基磺酰基，未取代或被选自C1-C8烷基、卤素、苯基中的至少一个基团取代的C3-C8环烷基，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、杂环基羰基C1-C8烷基、芳基羰基C1-C8烷基、杂芳基羰基C1-C8烷基、杂环基羰基氧基C1-C8烷基、芳基羰基氧基C1-C8烷基、杂芳基羰基氧基C1-C8烷基； Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C8)alkyl-OR 4 , -O-(C1-C8)alkyl-N(R 5 ) 2 , -(C1-C8)alkyl -O-(C1-C8)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C8)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C8)alkyl-N(R 5 ) 2 , C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxycarbonyl, C1- C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy C1-C8 alkyl, C1-C8 alkylthio , C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C8 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl, heterocyclylcarbonyl C1-C8 alkyl , Arylcarbonyl C1-C8 alkyl, heteroarylcarbonyl C1-C8 alkyl, heterocyclic carbonyloxy C1-C8 alkyl, arylcarbonyloxy C1-C8 alkyl, heteroarylcarbonyloxy C1 -C8 alkyl;M代表氢，OR 6，SR 6，COR 6，COOR 6，OCOR 6，CON(R 7) 2，N(R 7) 2，NR 8COOR 6，NR 8CON(R 7) 2，-(C1-C8烷基)-R，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，以及未取代或取代的芳基C1-C8烷基、杂芳基C1-C8烷基； M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C8 alkyl)-R, C1-C8 alkyl without or containing halogen, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and unsubstituted or substituted aryl C1-C8 Alkyl, heteroaryl C1-C8 alkyl;R代表不含或含有卤素的C2-C8烯基、C2-C8炔基、C3-C8环烷基，CN，OR 11，OCOR 11，COOR 11，COR 11，-O-(C＝O)-O-R 11，OSO 2R 12，SO 2OR 11，-S(O) nR 12，N(R 13) 2，CON(R 13) 2，SO 2N(R 13) 2，NR 14COR 11，NR 14SO 2R 12，-O-(C＝O)-N(R 13) 2； R represents C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl without or containing halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;R 4、R 6、R 11分别独立地代表氢、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、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C1-C8烷氧基C1-C8烷基，以及未取代或取代的杂环基、杂环基C1-C8烷基、杂环基氧基C1-C8烷基、芳基、芳基C1-C8烷基、芳基氧基C1-C8烷基、杂芳基、杂芳基C1-C8烷基、杂芳基氧基C1-C8烷基； R 4 , R 6 , and R 11 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkane C1-C8 alkyl, C3-C8 cycloalkenyl, C1-C8 alkoxy C1-C8 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C8 alkyl, heterocyclyloxy C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryloxy C1-C8 alkyl, heteroaryl, heteroaryl C1-C8 alkyl, heteroaryloxy C1-C8 alkyl ;R 3、R 12分别独立地代表不含或含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烷基C1-C8烷基、C3-C8环烯基、C1-C8烷氧基C1-C8烷基，以及未取代或取代的杂环基、杂环基C1-C8烷基、芳基、芳基C1-C8烷基、杂芳基、杂芳基C1-C8烷基； R 3 and R 12 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, C3-C8 cycloalkenyl group, C1-C8 alkoxy C1-C8 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C8 alkyl group, aryl group, aryl C1-C8 alkyl group , Heteroaryl, heteroaryl C1-C8 alkyl;R 1、R 2、R 5、R 7、R 8、R 13、R 14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R 21) 2、CON(R 21) 2、OR 21、COR 21、CO 2R 21、COSR 21、OCOR 21、S(O) rR 22、C1-C8烷基、卤代C1-C8烷基、C2-C8烯基、卤代C2-C8烯基、C2-C8炔基、卤代C2-C8炔基、C3-C8环烷基、C3-C8环烯基、卤代C3-C8环烷基、C1-C8烷氧基C1-C8烷基、C3-C8环烷基C1-C8烷基、芳基、芳基C1-C8烷基、芳基氧基、芳基氧基C1-C8烷基、芳基C1-C8烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C8烷基、杂芳基氧基、杂芳基氧基C1-C8烷基、杂芳基C1-C8烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C8烷基、杂环基氧基、杂环基氧基C1-C8烷基、杂环基C1-C8烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR 21-(C1-C8)烷基、杂芳基-NR 21-(C1-C8)烷基、杂环基-NR 21-(C1-C8)烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR 21、S(O) rR 22、N(R 21) 2、NR 21OR 21、COR 21、OCOR 21、SCOR 22、NR 21COR 21、NR 21SO 2R 22、CO 2R 21、COSR 21、CON(R 21) 2和C1-C8烷氧基C1-C8烷氧基羰基； R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C8 alkyl, halogenated C1-C8 alkyl , C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, halogenated C3-C8 cycloalkane Group, C1-C8 alkoxy C1-C8 alkyl, C3-C8 cycloalkyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryloxy, aryloxy C1-C8 alkyl Group, aryl C1-C8 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C8 alkyl, heteroaryloxy, heteroaryloxy C1-C8 alkyl , Heteroaryl C1-C8 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C8 alkyl, heterocyclyloxy, heterocyclyloxy C1-C8 Alkyl, heterocyclyl C1-C8 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C8)alkyl, heteroaryl-NR 21 -(C1-C8 )Alkyl, heterocyclyl-NR 21 -(C1-C8)alkyl, wherein the last-mentioned 35 groups are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C8 alkoxy C1-C8 alkoxycarbonyl;R 21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； R 21 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;R 22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； R 22 independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl;m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;其中，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，“杂芳基”是指
其中，其任选地可被选自卤素，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、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”，被选自氢、烷基、烯基、炔基、环烷基、环烷基烷基、COR”、SO 2R”、OR”中的一个或两个基团所取代的氨基或氨基羰基，以及-OCH 2CH 2-，-OCH 2O-，-OCH 2CH 2O-中的至少一个基团所取代； Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups
The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers toWherein, it may optionally be selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxy, mercapto, formyl, unsubstituted or selected from at least one group selected from halogen, alkyl, alkoxy Phenyl, benzyl, phenoxy substituted by groups, with or without halogen alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, OR", SR", -alkyl-OR ", -alkyl-SR", COR", COOR", COSR", SOR", SO 2 R", OCOR", SCOR" are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, Amino or aminocarbonyl substituted by one or two groups of cycloalkylalkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by at least one group;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'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”分别独立地代表氢，含有或不含有卤素的烷基、烯基、炔基、环烷基或环烷基烷基。R" independently represents hydrogen, alkyl or alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl with or without halogen. - 根据权利要求1或2所述的一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其特征在于，An N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or a salt thereof according to claim 1 or 2, whereinX代表O、S、SO、SO 2或NR 1； X represents O, S, SO, SO 2 or NR 1 ;Y代表卤素，氰基，氰基C1-C6烷基，羧基，硝基，N(R 2) 2，-(C1-C6)烷基-N(R 2) 2，CON(R 2) 2，-(C1-C6)烷基-CON(R 2) 2，-(C1-C6)烷基-N(R 2) 3 +I -，羟基C1-C6烷基，被氨基和羧基取代的C1-C6烷基，OR 3，SR 3，-(C1-C6)烷基-SOR 3，-(C1-C6)烷基-OR 3，-(C1-C6)烷基-SR 3，COR 3，COOR 3，-(C1-C6)烷基-COR 4，-(C1-C6)烷基-COOR 4，-(C1-C6)烷基-OCOR 3，Si(R 3) 3，-(C1-C6)烷基-O-Si(R 3) 3，-(C1-C6)烷基-O-N＝C(R 3) 2，C1-C6烷基，卤代C1-C6烷基，未取代或被选自卤素、氰基、C3-C6环烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、三C1-C6烷基硅基中的至少一个基团所取代的C2-C6烯基、C2-C6炔基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基、C3-C6环烷基C1-C6烷基，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； Y represents halogen, cyano, cyano C1-C6 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C6)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C6) alkyl -CON (R 2) 2, - (C1-C6) alkyl -N (R 2) 3 + I -, hydroxy C1-C6 alkyl, substituted amino and carboxyl C1- C6 alkyl, OR 3 , SR 3 , -(C1-C6)alkyl-SOR 3 , -(C1-C6)alkyl-OR 3 , -(C1-C6)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C6)alkyl-COR 4 ,-(C1-C6)alkyl-COOR 4 ,-(C1-C6)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C6 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C6)alkyl-ON=C(R 3 ) 2 ,C1-C6 alkyl, halogenated C1-C6 alkyl, unsubstituted or selected From halogen, cyano, C3-C6 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl , C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl substituted by at least one group of tri-C1-C6 alkylsilyl, unsubstituted or selected from C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl substituted with at least one group of halogen and phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl;或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，巯基，甲酰基，未取代或被选自卤素、C1-C8烷基、C1-C8烷氧基中的1、2或3个基团所取代的苯基、苄基、苯氧基，以及含有或不含有卤素的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、C1-C8烷硫基、C1-C8烷氧基C1-C8烷基、C1-C8烷硫基C1-C8烷基、C1-C8烷基羰基、C1-C8烷氧基羰基、C1-C8烷基亚硫酰基、C1-C8烷基磺酰基、C1-C8烷基氨基、二C1-C8烷基氨基、C1-C8烷基酰氧基中的1、2或3个基团所 取代的
Or -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxy, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 with or without halogen Cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1- C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, di-C1-C8 alkylamino , C1-C8 alkylacyloxy substituted by 1, 2 or 3 groups
Z代表氢，卤素，氰基，OR 4，-(C1-C6)烷基-OR 4，-O-(C1-C6)烷基-N(R 5) 2，-(C1-C6)烷基-O-(C1-C6)烷基-N(R 5) 2，N(R 5) 2，-(C1-C6)烷基-(C＝O) m-N(R 5) 2，-NH-(C1-C6)烷基-N(R 5) 2，不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C6烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷基羰基氧基C1-C6烷基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基，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、杂环基羰基C1-C6烷基、芳基羰基C1-C6烷基、杂芳基羰基C1-C6烷基、杂环基羰基氧基C1-C6烷基、芳基羰基氧基C1-C6烷基、杂芳基羰基氧基C1-C6烷基； Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C6)alkyl-OR 4 , -O-(C1-C6)alkyl-N(R 5 ) 2 ,-(C1-C6)alkyl -O-(C1-C6)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C6)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C6)alkyl-N(R 5 ) 2 , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxycarbonyl, C1- C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy C1-C6 alkyl, C1-C6 alkylthio , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl, heterocyclylcarbonyl C1-C6 alkyl , Arylcarbonyl C1-C6 alkyl, heteroarylcarbonyl C1-C6 alkyl, heterocyclic carbonyloxy C1-C6 alkyl, arylcarbonyloxy C1-C6 alkyl, heteroarylcarbonyloxy C1 -C6 alkyl;M代表氢，OR 6，SR 6，COR 6，COOR 6，OCOR 6，CON(R 7) 2，N(R 7) 2，NR 8COOR 6，NR 8CON(R 7) 2，-(C1-C6烷基)-R，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，以及未取代或取代的芳基C1-C6烷基、杂芳基C1-C6烷基； M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C6 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C1-C6 unsubstituted or substituted aryl Alkyl, heteroaryl C1-C6 alkyl;R代表不含或含有卤素的C2-C6烯基、C2-C6炔基、C3-C6环烷基，CN，OR 11，OCOR 11，COOR 11，COR 11，-O-(C＝O)-O-R 11，OSO 2R 12，SO 2OR 11，-S(O) nR 12，N(R 13) 2，CON(R 13) 2，SO 2N(R 13) 2，NR 14COR 11，NR 14SO 2R 12，-O-(C＝O)-N(R 13) 2； R represents C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl without or with halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;R 4、R 6、R 11分别独立地代表氢、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、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C1-C6烷氧基C1-C6烷基，以及未取代或取代的杂环基、杂环基C1-C6烷基、杂环基氧基C1-C6烷基、芳基、芳基C1-C6烷基、芳基氧基C1-C6烷基、杂芳基、杂芳基C1-C6烷基、杂芳基氧基C1-C6烷基； R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C6 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C6 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C6 alkyl, heterocyclyloxy C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy C1-C6 alkyl ;R 3、R 12分别独立地代表不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C6烷基、C3-C6环烯基、C1-C6烷氧基C1-C6烷基，以及未取代或取代的杂环基、杂环基C1-C6烷基、芳基、芳基C1-C6烷基、杂芳基、杂芳基C1-C6烷基； R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C6 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C6 alkyl group, aryl group, aryl C1-C6 alkyl group , Heteroaryl, heteroaryl C1-C6 alkyl;R 1、R 2、R 5、R 7、R 8、R 13、R 14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R 21) 2、CON(R 21) 2、OR 21、COR 21、CO 2R 21、COSR 21、OCOR 21、S(O) rR 22、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、C3-C6环烯基、卤代C3-C6环烷基、C1-C6烷氧基C1-C6烷基、 C3-C6环烷基C1-C6烷基、芳基、芳基C1-C6烷基、芳基氧基、芳基氧基C1-C6烷基、芳基C1-C6烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C6烷基、杂芳基氧基、杂芳基氧基C1-C6烷基、杂芳基C1-C6烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C6烷基、杂环基氧基、杂环基氧基C1-C6烷基、杂环基C1-C6烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR 21-(C1-C6)烷基、杂芳基-NR 21-(C1-C6)烷基、杂环基-NR 21-(C1-C6)烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR 21、S(O) rR 22、N(R 21) 2、NR 21OR 21、COR 21、OCOR 21、SCOR 22、NR 21COR 21、NR 21SO 2R 22、CO 2R 21、COSR 21、CON(R 21) 2和C1-C6烷氧基C1-C6烷氧基羰基； R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkane Group, C1-C6 alkoxy C1-C6 alkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy, aryloxy C1-C6 alkyl Group, aryl C1-C6 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy, heteroaryloxy C1-C6 alkyl , Heteroaryl C1-C6 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C6 alkyl, heterocyclyloxy, heterocyclyloxy C1-C6 Alkyl, heterocyclyl C1-C6 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C6)alkyl, heteroaryl-NR 21 -(C1-C6 )Alkyl, heterocyclyl-NR 21 -(C1-C6)alkyl, wherein the last-mentioned 35 groups are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C6 alkoxy C1-C6 alkoxycarbonyl;R 21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； R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;R 22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； R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl;m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;其中，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，“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-C8烷基、C1-C8烷氧基中的1、2或3个基团所取代的苯基、苄基、苯氧基，含有或不含有卤素的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、OR”、SR”、-(C1-C8)烷基-OR”、-(C1-C8)烷基-SR”、COR”、COOR”、COSR”、SOR”、SO 2R”、OCOR”、SCOR”，被选自氢、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、COR”、SO 2R”、OR”中的一个或两个基团所取代的氨基或氨 基羰基，以及-OCH 2CH 2-，-OCH 2O-，-OCH 2CH 2O-中的0、1、2或3个基团所取代； Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups
The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers toAmong them, it is selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C8 alkyl, C1-C8 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl , C3-C8 cycloalkyl C1-C8 alkyl, OR", SR", -(C1-C8)alkyl-OR", -(C1-C8)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 ring Amino or aminocarbonyl substituted with one or two groups of alkyl C1-C8 alkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by 0, 1, 2 or 3 groups;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-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基、C3-C8环烯基、C3-C8环烷基C1-C8烷基、C1-C8烷氧基、C2-C8烯基氧基、C2-C8炔基氧基、C3-C8环烷基氧基、C1-C8烷氧基C1-C8烷基、C1-C8烷氧基羰基、C1-C8烷硫基羰基、C1-C8烷基磺酰基、C1-C8烷基磺酰基C1-C8烷基、C1-C8烷基羰基、C1-C8烷基羰基C1-C8烷基、C1-C8烷基酰氧基、C1-C8烷基氨基、C1-C8烷基氨基羰基、C1-C8烷氧基氨基羰基、C1-C8烷氧基羰基C1-C8烷基、C1-C8烷氨基羰基C1-C8烷基、三C1-C8烷基甲硅烷基、二C1-C8烷基膦酰基；R'independently represents hydrogen, nitro, hydroxy, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, with or without fluorine, chlorine, or bromine C3-C8 cycloalkenyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy , C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthiocarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylsulfonyl C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkylacyloxy, C1-C8 alkylamino, C1-C8 alkylaminocarbonyl, C1-C8 alkoxyamino Carbonyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylaminocarbonyl C1-C8 alkyl, tri-C1-C8 alkylsilyl, di-C1-C8 alkylphosphono;R”分别独立地代表氢，含有或不含有卤素的C1-C8烷基、C2-C8烯基、C2-C8炔基、C3-C8环烷基或C3-C8环烷基C1-C8烷基。R” independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl C1-C8 alkyl with or without halogen . - 根据权利要求1-3任意一项所述的一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其特征在于，An N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or a salt thereof according to any one of claims 1-3, characterized in thatX代表O、S、SO、SO 2或NR 1； X represents O, S, SO, SO 2 or NR 1 ;Y代表卤素，氰基，氰基C1-C2烷基，羧基，硝基，N(R 2) 2，-(C1-C2)烷基-N(R 2) 2，CON(R 2) 2，-(C1-C2)烷基-CON(R 2) 2，-(C1-C2)烷基-N(R 2) 3 +I -，羟基C1-C2烷基，被氨基和羧基取代的C1-C2烷基，OR 3，SR 3，-(C1-C2)烷基-SOR 3，-(C1-C2)烷基-OR 3，-(C1-C2)烷基-SR 3，COR 3，COOR 3，-(C1-C2)烷基-COR 4，-(C1-C2)烷基-COOR 4，-(C1-C2)烷基-OCOR 3，Si(R 3) 3，-(C1-C2)烷基-O-Si(R 3) 3，-(C1-C2)烷基-O-N＝C(R 3) 2，C1-C6烷基，卤代C1-C6烷基，未取代或被选自卤素、氰基、C3-C6环烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、三C1-C6烷基硅基中的至少一个基团所取代的C2-C6烯基、C2-C6炔基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基、C3-C6环烷基C1-C2烷基，未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C2烷基、芳基C1-C2烷基、杂芳基C1-C2烷基； Y represents halogen, cyano, cyano C1-C2 alkyl, carboxyl, nitro, N(R 2 ) 2 , -(C1-C2)alkyl-N(R 2 ) 2 , CON(R 2 ) 2 , - (C1-C2) alkyl -CON (R 2) 2, - (C1-C2) alkyl -N (R 2) 3 + I -, hydroxy C1-C2 alkyl, substituted amino and carboxyl C1- C2 alkyl, OR 3 , SR 3 , -(C1-C2)alkyl-SOR 3 , -(C1-C2)alkyl-OR 3 , -(C1-C2)alkyl-SR 3 , COR 3 , COOR 3 , -(C1-C2)alkyl-COR 4 ,-(C1-C2)alkyl-COOR 4 ,-(C1-C2)alkyl-OCOR 3 ,Si(R 3 ) 3 ,-(C1-C2 )Alkyl-O-Si(R 3 ) 3 ,-(C1-C2)alkyl-ON=C(R 3 ) 2 ,C1-C6 alkyl, halogenated C1-C6 alkyl, unsubstituted or selected From halogen, cyano, C3-C6 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl , C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl substituted by at least one group of tri-C1-C6 alkylsilyl, unsubstituted or selected from C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl substituted with at least one group of halogen, phenyl, unsubstituted or substituted heterocyclic group, aryl group, heteroaryl group, heterocyclic group C1-C2 alkyl, aryl C1-C2 alkyl, heteroaryl C1-C2 alkyl;或者-X-Y代表未取代或被选自卤素，硝基，氰基，羟基，羧基，氨基，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1、2或3个基团所取代的苯基、苄基、苯氧基，以及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-C2烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氧基C1-C2烷基、C1-C6烷硫基C1-C2烷基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6烷基氨基、二C1-C6烷基氨基、C1-C6烷基酰氧基中的1、2或3个基团所 取代的
Or -XY represents unsubstituted or selected from halogen, nitro, cyano, hydroxyl, carboxyl, amino, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy Phenyl, benzyl, phenoxy substituted by 1, 2 or 3 groups, and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 with or without halogen Cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkylthio C1- C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, di-C1-C6 alkylamino , Substituted by 1, 2 or 3 groups in C1-C6 alkylacyloxy
Z代表氢，卤素，氰基，OR 4，-(C1-C2)烷基-OR 4，-O-(C1-C2)烷基-N(R 5) 2，-(C1-C2)烷基-O-(C1-C2)烷基-N(R 5) 2，N(R 5) 2，-(C1-C2)烷基-(C＝O) m-N(R 5) 2，-NH-(C1-C2)烷基-N(R 5) 2，不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C2烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C2烷基、C1-C6烷基羰基氧基C1-C2烷基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基，未取代或被选自C1-C6烷基、卤素、苯基中的至少一个基团取代的C3-C6环烷基，未取代或取代的杂环基、芳基、杂芳基、杂环基C1-C2烷基、芳基C1-C2烷基、杂芳基C1-C2烷基、杂环基羰基C1-C2烷基、芳基羰基C1-C2烷基、杂芳基羰基C1-C2烷基、杂环基羰基氧基C1-C2烷基、芳基羰基氧基C1-C2烷基、杂芳基羰基氧基C1-C2烷基； Z represents hydrogen, halogen, cyano, OR 4 , -(C1-C2)alkyl-OR 4 , -O-(C1-C2)alkyl-N(R 5 ) 2 , -(C1-C2)alkyl -O-(C1-C2)alkyl-N(R 5 ) 2 ,N(R 5 ) 2 ,-(C1-C2)alkyl-(C=O) m -N(R 5 ) 2 ,-NH -(C1-C2)alkyl-N(R 5 ) 2 , C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxycarbonyl, C1- C6 alkoxycarbonyl C1-C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C2 alkyl, C1-C6 alkylcarbonyloxy C1-C2 alkyl, C1-C6 alkylthio , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen, phenyl, Substituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C2 alkyl, aryl C1-C2 alkyl, heteroaryl C1-C2 alkyl, heterocyclylcarbonyl C1-C2 alkyl , Arylcarbonyl C1-C2 alkyl, heteroarylcarbonyl C1-C2 alkyl, heterocyclic carbonyloxy C1-C2 alkyl, arylcarbonyloxy C1-C2 alkyl, heteroarylcarbonyloxy C1 -C2 alkyl;M代表氢，OR 6，SR 6，COR 6，COOR 6，OCOR 6，CON(R 7) 2，N(R 7) 2，NR 8COOR 6，NR 8CON(R 7) 2，-(C1-C2烷基)-R，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，以及未取代或取代的芳基C1-C2烷基、杂芳基C1-C2烷基； M represents hydrogen, OR 6 , SR 6 , COR 6 , COOR 6 , OCOR 6 , CON(R 7 ) 2 , N(R 7 ) 2 , NR 8 COOR 6 , NR 8 CON(R 7 ) 2 , -(C1 -C2 alkyl)-R, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and unsubstituted or substituted aryl C1-C2 Alkyl, heteroaryl C1-C2 alkyl;R代表不含或含有卤素的C2-C6烯基、C2-C6炔基、C3-C6环烷基，CN，OR 11，OCOR 11，COOR 11，COR 11，-O-(C＝O)-O-R 11，OSO 2R 12，SO 2OR 11，-S(O) nR 12，N(R 13) 2，CON(R 13) 2，SO 2N(R 13) 2，NR 14COR 11，NR 14SO 2R 12，-O-(C＝O)-N(R 13) 2； R represents C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl without or with halogen, CN, OR 11 , OCOR 11 , COOR 11 , COR 11 , -O-(C=O)- OR 11 , OSO 2 R 12 , SO 2 OR 11 , -S(O) n R 12 , N(R 13 ) 2 , CON(R 13 ) 2 , SO 2 N(R 13 ) 2 , NR 14 COR 11 , NR 14 SO 2 R 12 , -O-(C=O)-N(R 13 ) 2 ;R 4、R 6、R 11分别独立地代表氢、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、C3-C6环烷基C1-C2烷基、C3-C6环烯基、C1-C6烷氧基C1-C2烷基，以及未取代或取代的杂环基、杂环基C1-C2烷基、杂环基氧基C1-C2烷基、芳基、芳基C1-C2烷基、芳基氧基C1-C2烷基、杂芳基、杂芳基C1-C2烷基、杂芳基氧基C1-C2烷基； R 4 , R 6 , and R 11 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkane C1-C2 alkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy C1-C2 alkyl, and unsubstituted or substituted heterocyclyl, heterocyclyl C1-C2 alkyl, heterocyclyloxy C1-C2 alkyl, aryl, aryl C1-C2 alkyl, aryloxy C1-C2 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryloxy C1-C2 alkyl ;R 3、R 12分别独立地代表不含或含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C3-C6环烷基C1-C2烷基、C3-C6环烯基、C1-C6烷氧基C1-C2烷基，以及未取代或取代的杂环基、杂环基C1-C2烷基、芳基、芳基C1-C2烷基、杂芳基、杂芳基C1-C2烷基； R 3 and R 12 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl Group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C2 alkyl group, and unsubstituted or substituted heterocyclic group, heterocyclic group C1-C2 alkyl group, aryl group, aryl C1-C2 alkyl group , Heteroaryl, heteroaryl C1-C2 alkyl;R 1、R 2、R 5、R 7、R 8、R 13、R 14分别独立地代表氢、硝基、烷氧基氨基羰基、三烷基甲硅烷基、二烷基膦酰基、N(R 21) 2、CON(R 21) 2、OR 21、COR 21、CO 2R 21、COSR 21、OCOR 21、S(O) rR 22、C1-C6烷基、卤代C1-C6烷基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6环烷基、C3-C6环烯基、卤代C3-C6环烷基、C1-C6烷氧基C1-C2烷基、 C3-C6环烷基C1-C2烷基、芳基、芳基C1-C2烷基、芳基氧基、芳基氧基C1-C2烷基、芳基C1-C2烷基氧基、芳基羰基、芳基磺酰基、杂芳基、杂芳基C1-C2烷基、杂芳基氧基、杂芳基氧基C1-C2烷基、杂芳基C1-C2烷基氧基、杂芳基羰基、杂芳基磺酰基、杂环基、杂环基C1-C2烷基、杂环基氧基、杂环基氧基C1-C2烷基、杂环基C1-C2烷基氧基、杂环基羰基、杂环基磺酰基、芳基-NR 21-(C1-C2)烷基、杂芳基-NR 21-(C1-C2)烷基、杂环基-NR 21-(C1-C2)烷基，其中最后提及的35个基团各自被0、1、2或3个选自下述的基团取代：氰基、卤素、硝基、氰硫基、OR 21、S(O) rR 22、N(R 21) 2、NR 21OR 21、COR 21、OCOR 21、SCOR 22、NR 21COR 21、NR 21SO 2R 22、CO 2R 21、COSR 21、CON(R 21) 2和C1-C6烷氧基C1-C2烷氧基羰基； R 1 , R 2 , R 5 , R 7 , R 8 , R 13 , and R 14 independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphono, N( R 21 ) 2 , CON(R 21 ) 2 , OR 21 , COR 21 , CO 2 R 21 , COSR 21 , OCOR 21 , S(O) r R 22 , C1-C6 alkyl, halogenated C1-C6 alkyl , C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkan Group, C1-C6 alkoxy C1-C2 alkyl, C3-C6 cycloalkyl C1-C2 alkyl, aryl, aryl C1-C2 alkyl, aryloxy, aryloxy C1-C2 alkyl Group, aryl C1-C2 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryloxy, heteroaryloxy C1-C2 alkyl , Heteroaryl C1-C2 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C1-C2 alkyl, heterocyclyloxy, heterocyclyloxy C1-C2 Alkyl, heterocyclyl C1-C2 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR 21 -(C1-C2)alkyl, heteroaryl-NR 21 -(C1-C2 ) Alkyl, heterocyclyl-NR 21 -(C1-C2)alkyl, wherein the last 35 groups mentioned are each substituted with 0, 1, 2 or 3 groups selected from the group consisting of: cyano, Halogen, nitro, cyanothio, OR 21 , S(O) r R 22 , N(R 21 ) 2 , NR 21 OR 21 , COR 21 , OCOR 21 , SCOR 22 , NR 21 COR 21 , NR 21 SO 2 R 22 , CO 2 R 21 , COSR 21 , CON(R 21 ) 2 and C1-C6 alkoxy C1-C2 alkoxycarbonyl;R 21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-C2烷基； R 21 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;R 22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-C2烷基； R 22 independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl;m代表0或1，n、r分别独立地代表0、1或2；m represents 0 or 1, n and r independently represent 0, 1 or 2;其中，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，“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1、2或3个基团所取代的苯基、苄基、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-C2烷基、OR”、SR”、-(C1-C2)烷基-OR”、-(C1-C2)烷基-SR”、COR”、COOR”、COSR”、SOR”、SO 2R”、OCOR”、SCOR”，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-C2烷基、COR”、SO 2R”、OR”中的一个或两个基团所取代的氨基或氨 基羰基，以及-OCH 2CH 2-，-OCH 2O-，-OCH 2CH 2O-中的0、1、2或3个基团所取代； Wherein, the "heterocyclic group" refers to a group having 0, 1, or 2 oxo groups
The "aryl" refers to phenyl and naphthyl, and "heteroaryl" refers toAmong them, it is selected from halogen, nitro, cyano, cyanothio, hydroxy, carboxyl, mercapto, formyl, unsubstituted or selected from halogen, C1-C6 alkyl, C1-C6 alkoxy 1 , 2 or 3 groups substituted phenyl, benzyl, phenoxy, with or without halogen C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl , C3-C6 cycloalkyl C1-C2 alkyl, OR", SR", -(C1-C2)alkyl-OR", -(C1-C2)alkyl-SR", COR", COOR", COSR ", SOR", SO 2 R", OCOR", SCOR" selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 ring Amino or aminocarbonyl substituted with one or two groups of alkyl C1-C2 alkyl, COR", SO 2 R", OR", and -OCH 2 CH 2 -, -OCH 2 O-, -OCH 2 CH 2 O- substituted by 0, 1, 2 or 3 groups;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-C8环烷基C1-C2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-C2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-C2烷基、C1-C6烷基羰基、C1-C6烷基羰基C1-C2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-C2烷基、C1-C6烷氨基羰基C1-C2烷基、三C1-C6烷基甲硅烷基、二C1-C6烷基膦酰基；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-C8 cycloalkyl C1-C2 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy , C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C2 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C2 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyamino Carbonyl, C1-C6 alkoxycarbonyl C1-C2 alkyl, C1-C6 alkylaminocarbonyl C1-C2 alkyl, tri-C1-C6 alkylsilyl, di-C1-C6 alkylphosphono;R”分别独立地代表氢，含有或不含有卤素的C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基或C3-C6环烷基C1-C2烷基。R" independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C2 alkyl with or without halogen . - 根据权利要求1或2所述的一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其特征在于，An N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or a salt thereof according to claim 1 or 2, whereinX代表S、SO或SO 2； X stands for S, SO or SO 2 ;Y代表C2-C8烷基，卤代C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C8烷氧基C1-C8烷基，羟基C1-C8烷基，氰基，氰基C1-C8烷基，氨基C1-C8烷基，C1-C8烷氨基C1-C8烷基，C1-C8烷基羰基，C3-C8环烷基，C3-C8环烷基C1-C8烷基，二C1-C8烷氨基羰基C1-C8烷基，C1-C8烷基羰基C1-C8烷基，C1-C8烷氧基羰基C1-C8烷基，C1-C8烷基羰基氧基C1-C8烷基，C1-C8烷基亚砜基C1-C8烷基，三C1-C8烷基硅氧基C1-C8烷基，杂环基，杂环基C1-C8烷基，苯基，杂芳基，杂芳基C1-C8烷基，-(C1-C8)烷基-O-N＝C(R”’) 2； Y represents C2-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy C1-C8 alkyl, hydroxy C1-C8 alkyl, cyano, Cyano C1-C8 alkyl, amino C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl Group, di-C1-C8 alkylaminocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyl C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy C1- C8 alkyl, C1-C8 alkylsulfoxide C1-C8 alkyl, tri-C1-C8 alkylsiloxy C1-C8 alkyl, heterocyclic, heterocyclic C1-C8 alkyl, phenyl, hetero Aryl, heteroaryl C1-C8 alkyl, -(C1-C8)alkyl-ON=C(R"') 2 ;其中，杂环基为杂芳基为未取代或被C1-C8烷基取代的
R”’分别独立地代表C1-C8烷基； Among them, the heterocyclic group is
Heteroaryl is unsubstituted or substituted by C1-C8 alkylR"' independently represents C1-C8 alkyl;Z代表氢，C1-C8烷基；Z represents hydrogen, C1-C8 alkyl;M代表氢，C1-C8烷氧基羰基氧基C1-C8烷基；M represents hydrogen, C1-C8 alkoxycarbonyloxy C1-C8 alkyl;优选地，X代表S、SO或SO 2； Preferably, X represents S, SO or SO 2 ;Y代表C2-C6烷基，卤代C1-C6烷基，C2-C6烯基，C2-C6炔基，C1-C6烷氧基C1-C6烷基，羟基C1-C6烷基，氰基，氰基C1-C6烷基，氨基C1-C6烷基，C1-C6烷氨基C1-C6烷基，C1-C6烷基羰基，C3-C6环烷基，C3-C6环烷基C1-C6烷基，二C1-C6烷氨基羰基C1-C6烷基，C1-C6烷基羰基C1-C6烷基，C1-C6烷氧基羰基C1-C6烷基，C1-C6烷基羰基氧基C1-C6烷基，C1-C6烷基亚砜基C1-C6烷基，三C1-C6烷基硅氧基C1-C6烷基，杂环基，杂环基C1-C6烷基，苯基，杂芳基，杂芳基C1-C6烷基，-(C1-C6)烷基-O-N＝C(R”’) 2； Y represents C2-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, hydroxy C1-C6 alkyl, cyano, Cyano C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl Group, di-C1-C6 alkylaminocarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy C1- C6 alkyl, C1-C6 alkyl sulfoxide C1-C6 alkyl, tri-C1-C6 alkylsiloxy C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, phenyl, hetero Aryl, heteroaryl C1-C6 alkyl, -(C1-C6)alkyl-ON=C(R"') 2 ;其中，杂环基为杂芳基为未取代或被C1-C6烷基取代的
R”’分别独立地代表C1-C6烷基； Among them, the heterocyclic group is
Heteroaryl is unsubstituted or substituted with C1-C6 alkylR"' independently represents C1-C6 alkyl;Z代表氢，C1-C6烷基；Z represents hydrogen, C1-C6 alkyl;M代表氢，C1-C6烷氧基羰基氧基C1-C6烷基。M represents hydrogen, C1-C6 alkoxycarbonyloxy C1-C6 alkyl. - 根据权利要求1-5任意一项所述的一种N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐，其特征在于，化合物结构为基团Y、Z、M定义如权利要求1-5任意一项所述，优选地，化合物选自表A1-A151和表1-3中任意一个。 An N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or a salt thereof according to any one of claims 1-5, wherein the compound structure is
The definition of the groups Y, Z, M is as described in any one of claims 1-5, preferably, the compound is selected from any one of Tables A1-A151 and Tables 1-3. - 一种如权利要求1-6任意一项所述的N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐的制备方法，其特征在于，A method for preparing N-(1,3,4-oxadiazol-2-yl)aryl formamide compounds or salts thereof according to any one of claims 1-6, characterized in thata)当通式I中X代表Q时，其制备方法包括以下步骤：a) When X in the general formula I represents Q, the preparation method includes the following steps:将如通式Ⅴ所示的化合物与Ⅵ所示的化合物反应制得如通式I-1所示的化合物，其反应方程式如下：The compound represented by the general formula V is reacted with the compound represented by the VI to obtain the compound represented by the general formula I-1, the reaction equation is as follows:
其中，Q代表O、S、NR 1； Among them, Q stands for O, S, NR 1 ;优选地，所述反应在卤化剂、催化剂和溶剂的存在下进行；更优选地，所述卤化剂为SOCl 2，所述催化剂为4-二甲氨基吡啶，所述溶剂为吡啶；所述反应温度为0～50℃； Preferably, the reaction is performed in the presence of a halogenating agent, a catalyst, and a solvent; more preferably, the halogenating agent is SOCl 2 , the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine; the reaction The temperature is 0～50℃;或者，b)当通式I中X代表S时，其制备方法包括如下步骤：Or, b) When X in the general formula I represents S, the preparation method includes the following steps:将如通式Ⅶ所示的化合物与Hal-Y反应制备如通式I-3所示化合物，其反应方程式如下：The compound represented by the general formula VII is reacted with Hal-Y to prepare the compound represented by the general formula I-3, and the reaction equation is as follows:
其中，Hal代表卤素，优选氟、氯或溴；Among them, Hal represents halogen, preferably fluorine, chlorine or bromine;优选地，该反应在碱和溶剂的存在下进行；更优选地，所述碱选自碳酸钾、碳酸钠中的一种或两种组合，所述溶剂选自DCM、DCE、ACN、THF、DMF中的一种或多种组合；所述反应温度为0～25℃；Preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or two of potassium carbonate and sodium carbonate, and the solvent is selected from DCM, DCE, ACN, THF, One or more combinations of DMF; the reaction temperature is 0 ~ 25 ℃;或者，c)当通式I中X代表SO、SO 2时，其制备方法包括如下步骤： Or, c) When X in the general formula I represents SO and SO 2 , the preparation method includes the following steps:将如通式I-3所示的化合物与过氧化物反应，制得如通式I-4和/或I-5所示的化合物，其反应方程式如下：The compound represented by the general formula I-3 is reacted with peroxide to prepare the compound represented by the general formula I-4 and/or I-5, and the reaction equation is as follows:
优选地，所述过氧化物为所述反应在溶剂的存在下进行；更优选地，所述溶剂选自DCM、DCE中的一种或两种组合；所述反应温度为0～50℃； Preferably, the peroxide is
The reaction is performed in the presence of a solvent; more preferably, the solvent is selected from one or a combination of DCM and DCE; the reaction temperature is 0-50°C;或者，d)当通式I中M不为氢时，其制备方法包括如下步骤：Or, d) When M in general formula I is not hydrogen, the preparation method includes the following steps:将如通式I-1、I-4、I-5所示的化合物与Hal-M反应，分别制得如通式I-6、I-7、I-8所示的化合物，其反应方程式如下：The compounds represented by the general formula I-1, I-4, I-5 are reacted with Hal-M to prepare the compounds represented by the general formula I-6, I-7, I-8, respectively, and the reaction equation as follows:
优选地，所述反应在碱和溶剂的存在下进行；更优选地，所述碱选自碳酸钾、碳酸钠中的一种或两种组合，所述溶剂选自DCM、DCE、ACN、THF、DMF中的一种或多种组合，所述反应温度为0～100℃；或者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4-二甲氨基吡啶，所述溶剂为吡啶，所述反应温度为0～80℃。Preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate, and the solvent is selected from DCM, DCE, ACN, THF , DMF one or more combinations, the reaction temperature is 0 ~ 100 ℃; or the reaction is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is 4-dimethylaminopyridine, the The solvent is pyridine, and the reaction temperature is 0-80°C. - 一种除草组合物，其特征在于，包括(i)权利要求1-6任意一项如通式I所示的N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐；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；进一步优选地，所述另外的除草剂选自以下化合物或其盐、酯衍生物：A herbicidal composition, characterized in that it includes (i) N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as shown in general formula I according to any one of claims 1-6 Compounds or their salts; preferably, (ii) one or more additional herbicides and/or safeners; more preferably, (iii) agrochemically acceptable formulation adjuvants; further preferred Preferably, the additional herbicide is selected from the following compounds or their salt and ester derivatives:a)ALS抑制剂：吡嘧磺隆、五氟磺草胺、双草醚、嘧草醚、嗪吡嘧磺隆、丙嗪嘧磺隆、氟酮磺草胺；a) ALS inhibitors: pyrazosulfuron-methyl, penoxsulam, chlorfenapyr, chlorfenuron, azimesulfuron-methyl, promethazine-sulfuron-methyl, fluoxachlor;b)ACCase抑制剂：氰氟草酯、噁唑酰草胺；b) ACCase inhibitors: cyflufenazone, oxachlor;c)激素类抑制剂：二氯喹啉酸、2甲4氯、2,4-D、2,4-D丁酸、氯氟吡氧乙酸、氯氟吡啶酯、2甲4氯丁酸、麦草畏、二氯喹啉草酮、二氯吡啶酸、三氯吡氧乙酸；c) Hormone inhibitors: quinclorac, 2 methyl 4 chloro, 2,4-D, 2,4-D butyric acid, chlorofluoropyridine oxyacetic acid, chlorofluoropyridyl ester, 2 methyl 4 chlorobutyric acid, wheat straw Phoxa, quinclorac, diclofenac, triclofenac;d)细胞***抑制剂：二甲戊灵、仲丁灵；d) Cell division inhibitors: pendimethalin, zhongdingling;e)脂类合成(非ACC)抑制剂：禾草丹、禾草敌；e) Lipid synthesis (non-ACC) inhibitors: Hecaodan and Hecaodi;f)HPPD抑制剂：***磺草酮、双唑草酮、环吡氟草酮、硝磺草酮、双环磺草酮、呋喃磺草酮；f) HPPD inhibitors: triflumetrione, biprofenone, ciprofloxacin, mesotrione, bicyclosufenone, furansulfuron;g)PDS抑制剂：吡氟酰草胺、氟咯草酮、氟丁酰草胺；g) PDS inhibitors: flufluramide, fluroxypyr, flufluramide;h)PPO抑制剂：唑草酮、双唑草腈、噁草酮、丙炔噁草酮、乙氧氟草醚、环戊噁草酮；h) PPO inhibitors: chlorfenazone, azaprofon, oxadiazon, propynyl oxadiazon, oxyfluorfen, cyprofenone;i)长链脂肪酸合成抑制剂：丁草胺、丙草胺、苯噻酰草胺、莎稗膦、四唑酰草胺、异丙甲草胺、哌草磷、砜吡草唑；i) Inhibitors of long-chain fatty acid synthesis: butachlor, alachlor, fenclofen, fenpropan, tebuprofen, metolachlor, piperafos, sulfamethoxazole;j)PSⅡ抑制剂：西草净、扑草净、胺唑草酮、异丙隆、除草定、哒草特、绿麦隆、灭草松、敌稗、嗪草酮、莠去津、溴苯腈、辛酰溴苯腈、特丁津；j) PSⅡinhibitors: oxazepam, promethazine, azaprodone, isoproteron, herbicide, dazatect, chlormeron, bentazone, dipropanol, azachlor, atrazine, bromine Benzonitrile, octanoyl bromoxynil, terbutin;k)DOXP抑制剂：异噁草松；k) DOXP inhibitor: clomazone;l)其他：噁嗪草酮、环庚草醚、茚草酮。l) Others: Oxachlor, Cyclohexate, Indoxazone.
- 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N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐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，优选为籼稻、粳稻，所述杂草为禾本科杂草、阔叶杂草、莎草科杂草，优选为稻稗、千金子、稗草、马唐、狗尾草、鸭舌草、野慈菇、苘麻、反枝苋、繁缕、异型莎草、萤蔺。A method for controlling weeds, characterized by comprising a herbicidally effective amount of N-(1,3,4-oxadiazol-2-yl)arylformamide according to any one of claims 1-6 At least one of the compounds or salts thereof or the herbicide composition of claim 8 is used on plants or weed areas, preferably, the plant is rice, preferably indica rice, japonica rice, the weed is Gramineous weeds, broad-leaved weeds, sedge weeds, preferably rice barnyardgrass, Thousand gold, barnyardgrass, crabgrass, bristlegrass, rhododendron, wild mushroom, velvetleaf, Amaranthus retroflexus, Stellaria Shaped sedge, firefly.
- 如权利要求1-6任意一项所述的N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐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N-(1,3,4-噁二唑-2-基)芳基甲酰胺类化合物或其盐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，所述植物为水稻，优选为籼稻、粳稻，所述杂草为禾本科杂草、阔叶杂草、莎草科杂草，优选为稻稗、千金子、稗草、马唐、狗尾草、鸭舌草、野慈菇、苘麻、反枝苋、繁缕、异型莎草、萤蔺。At least one of N-(1,3,4-oxadiazol-2-yl)arylformamide compounds or salts thereof according to any one of claims 1-6 or claim 8 Use of the herbicide composition for controlling weeds, preferably, the N-(1,3,4-oxadiazol-2-yl)aryl formamide compound or its salt is used to control useful crops In the weeds, the useful crops are transgenic crops or crops treated by genome editing technology, more preferably, the plants are rice, preferably indica rice, japonica rice, the weeds are grass weeds, broad-leaved weeds Grass, Cyperaceae weeds, preferably rice barnyard grass, Thousand gold, barnyard grass, crabgrass, bristlegrass, rhododendron, wild mushroom, velvetleaf, amaranth, chickweed, sedge, firefly
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| BR112021010464-0A BR112021010464A2 (en) | 2018-11-30 | 2019-11-27 | N-(1,3,4-oxadiazol-2-yl)arylcarboxamides or salts thereof, methods of preparation, herbicidal compositions and uses thereof |
| JP2021530934A JP7419372B2 (en) | 2018-11-30 | 2019-11-27 | N-(1,3,4-oxadiazol-2-yl)arylcarboxamide or its salt, preparation method, herbicidal composition and use thereof |
| DE112019005943.2T DE112019005943T5 (en) | 2018-11-30 | 2019-11-27 | N- (1, 3, 4-oxadiazol-2-yl) arylcarboxamides or their salts, production methods, herbicidal compositions and uses thereof |
| AU2019386018A AU2019386018A1 (en) | 2018-11-30 | 2019-11-27 | N-(1, 3, 4-oxadiazole-2-yl)aryl formamides or salt thereof, preparation method therefor, herbicidal composition and use thereof |
| US17/298,303 US20230041563A1 (en) | 2018-11-30 | 2019-11-27 | N-(1,3,4-oxadiazol-2-yl)arylcarboxamides or salts thereof, preparation methods, herbicidal compositions and uses thereof |
| PH12021551236A PH12021551236A1 (en) | 2018-11-30 | 2021-05-28 | N-(1,3,4-oxadiazol-2-yl)arylcarboxamides or salts thereof, preparation methods, herbicidal compositions and uses thereof |
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| CN201911014193.5A CN111253333A (en) | 2018-11-30 | 2019-10-23 | N- (1,3, 4-oxadiazole-2-yl) aryl formamide or salt thereof, preparation method, herbicidal composition and application |
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