WO2020108518A1 - 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 - Google Patents
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 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
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- 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.
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Abstract
Description
化合物序号 | 稗草 | 苘麻 | 马唐 | 狗尾草 | 剂量(g a.i./ha) |
1-1 | N | 4 | 2 | 2 | 120 |
1-1 | 2 | 2 | 1 | 1 | 60 |
1-1 | 2 | N | 1 | 1 | 30 |
1-1 | 1 | N | 0 | 0 | 15 |
1-1 | 0 | N | 0 | 0 | 7.5 |
1-2(R构型) | 4 | N | 4 | 3 | 60 |
1-2(R构型) | 3 | N | 3 | 3 | 30 |
1-2(R构型) | 1 | N | 1 | 2 | 15 |
1-2(R构型) | 0 | N | 0 | 0 | 7.5 |
1-2 | 3 | 4 | 3 | 3 | 60 |
1-4 | N | 5 | 5 | 5 | 60 |
1-5(R构型) | 5 | N | 5 | 5 | 60 |
1-5(R构型) | 5 | N | 5 | 5 | 30 |
1-5(R构型) | 5 | N | 5 | 5 | 15 |
1-5(R构型) | 5 | N | 4 | 4 | 7.5 |
1-5(R构型) | 4 | N | 3 | 3 | 3.75 |
1-5 | 5 | 5 | 5 | 5 | 60 |
1-8(R构型) | 5 | N | 5 | 5 | 60 |
1-8(R构型) | 5 | N | 5 | 5 | 30 |
1-8(R构型) | 5 | N | 5 | 5 | 15 |
1-8(R构型) | 5 | N | 5 | 4 | 7.5 |
1-8(R构型) | 5 | N | 4 | 2 | 3.75 |
1-8 | 5 | 5 | 5 | 5 | 60 |
1-14(R构型) | 5 | N | 5 | 5 | 60 |
1-14(R构型) | 5 | N | 5 | 5 | 30 |
1-14(R构型) | 5 | N | 5 | 4 | 15 |
1-14(R构型) | 5 | N | 4 | 4 | 7.5 |
1-14 | N | 5 | 5 | 5 | 60 |
1-17 | N | 5 | 5 | 5 | 60 |
1-20 | N | 5 | 5 | 5 | 60 |
1-52 | N | 5 | 5 | 5 | 60 |
1-57(R构型) | 5 | N | 5 | 5 | 125 |
1-82(R构型) | 5 | N | 5 | 5 | 125 |
1-392(R构型) | 5 | N | 5 | 5 | 500 |
1-395(R构型) | 5 | N | 5 | 5 | 500 |
1-397(R构型) | 5 | N | 5 | 5 | 125 |
1-398(R构型) | 5 | N | 5 | 5 | 250 |
1-401(R构型) | 5 | N | 5 | 5 | 500 |
1-402(R构型) | 5 | N | 5 | 5 | 500 |
1-403(R构型) | 5 | N | 5 | 5 | 60 |
1-404(R构型) | 5 | N | 5 | 5 | 60 |
1-405(R构型) | 5 | N | 5 | 5 | 125 |
1-411(R构型) | 5 | N | 5 | 5 | 250 |
1-412(R构型) | 5 | N | 5 | 5 | 500 |
1-413(R构型) | 5 | N | 5 | 5 | 500 |
1-414(R构型) | 5 | N | 5 | 5 | 500 |
1-427(R构型) | 5 | N | 5 | 5 | 500 |
1-428(R构型) | 5 | N | 5 | 5 | 500 |
1-429(R构型) | 5 | N | 5 | 5 | 500 |
1-430(R构型) | 5 | N | 5 | 5 | 500 |
1-431(R构型) | 5 | N | 5 | 5 | 500 |
1-432(R构型) | 5 | N | 5 | 5 | 500 |
1-441(R构型) | 5 | N | 5 | 5 | 500 |
1-443(R构型) | 5 | N | 5 | 5 | 500 |
1-444(R构型) | 5 | N | 5 | 5 | 500 |
1-446(R构型) | 5 | N | 5 | 5 | 500 |
1-447(R构型) | 5 | N | 5 | 5 | 500 |
1-448(R构型) | 5 | N | 5 | 5 | 500 |
1-523(R构型) | 5 | N | 5 | 5 | 500 |
1-525(R构型) | 5 | N | 5 | 5 | 500 |
1-552(R构型) | 5 | N | 5 | 5 | 125 |
1-563(R构型) | 5 | N | N | N | 125 |
1-617(R构型) | 5 | N | 5 | 5 | 60 |
2-8(R构型) | 5 | N | 5 | 5 | 250 |
3-4 | 5 | N | 5 | 5 | 250 |
3-5(R构型) | 5 | N | 5 | 5 | 120 |
3-8(R构型) | 5 | N | 5 | 5 | 60 |
3-11(R构型) | 5 | N | 5 | 5 | 125 |
3-14(R构型) | 5 | N | 5 | 5 | 60 |
3-17(R构型) | 5 | N | 5 | 5 | 125 |
3-20(R构型) | 5 | N | 5 | 5 | 125 |
3-52(R构型) | 5 | N | 5 | 5 | 125 |
3-54 | 5 | N | 5 | 5 | 250 |
3-57(R构型) | 5 | N | 5 | 5 | 125 |
6-8(R构型) | 5 | N | 5 | 5 | 250 |
对照化合物A | N | 3 | 1 | 1 | 120 |
化合物序号 | 籼稻(黄华占) | 粳稻(淮稻5号) | 计量 | 水稻和稗草的选择指数 |
1-5 | 0 | 0 | 250g a.i./ha | >5 |
1-6 | 0 | 0 | 250g a.i./ha | >5 |
1-7 | 0 | 0 | 250g a.i./ha | >5 |
1-8 | 0 | 0 | 250g a.i./ha | >5 |
1-9 | 0 | 0 | 250g a.i./ha | >5 |
1-13 | 0 | 0 | 250g a.i./ha | >5 |
1-14 | 0 | 0 | 250g a.i./ha | >5 |
1-20 | 0 | 0 | 250g a.i./ha | >5 |
1-52 | 0 | 0 | 250g a.i./ha | >5 |
1-57 | 0 | 0 | 250g a.i./ha | >5 |
1-82 | 0 | 0 | 250g a.i./ha | >5 |
1-134 | 0 | 0 | 250g a.i./ha | >5 |
对照化合物B | 4 | 3 | 250g a.i./ha | 0.8 |
对照化合物B | 3 | 3 | 125g a.i./ha | 0.8 |
对照化合物C | 5 | 4 | 125g a.i./ha | 1.1 |
对照化合物D | 5 | 5 | 60g a.i./ha | 1 |
化合物序号 | 稗草 | 萤蔺 | 鸭舌草 | 水稻 |
1-4 | 5 | 5 | 5 | 0 |
1-5 | 5 | 5 | 5 | 0 |
1-6 | 5 | 5 | 5 | 0 |
1-8 | 5 | 5 | 5 | 0 |
1-11 | 5 | 5 | 5 | 0 |
1-14 | 5 | 5 | 5 | 0 |
1-57 | 5 | 5 | 5 | 0 |
1-76 | 5 | 5 | 5 | 0 |
组分(i)/化合物序号 | 组分(ii) |
1-3 | 吡嘧磺隆 |
1-3 | 五氟磺草胺 |
1-3 | 双草醚 |
1-3 | 嘧草醚 |
1-3 | 嗪吡嘧磺隆 |
1-3 | 丙嗪嘧磺隆 |
1-3 | 氟酮磺草胺 |
1-3 | 氰氟草酯 |
1-3 | 噁唑酰草胺 |
1-3 | 二氯喹啉酸 |
1-3 | 2甲4氯 |
1-3 | 2,4-D |
1-3 | 2,4-D丁酸 |
1-3 | 氯氟吡氧乙酸 |
1-3 | 氯氟吡啶酯 |
1-3 | 2甲4氯丁酸 |
1-3 | 麦草畏 |
1-3 | 二氯喹啉草酮 |
1-3 | 二氯吡啶酸 |
1-3 | 三氯吡氧乙酸 |
1-3 | 二甲戊灵 |
1-3 | 仲丁灵 |
1-3 | 禾草丹 |
1-3 | 禾草敌 |
1-3 | ***磺草酮 |
1-3 | 双唑草酮 |
1-3 | 环吡氟草酮 |
1-3 | 硝磺草酮 |
1-3 | 双环磺草酮 |
1-3 | 呋喃磺草酮 |
1-3 | 吡氟酰草胺 |
1-3 | 氟咯草酮 |
1-3 | 氟丁酰草胺 |
1-3 | 唑草酮 |
1-3 | 双唑草腈 |
1-3 | 噁草酮 |
1-3 | 丙炔噁草酮 |
1-3 | 乙氧氟草醚 |
1-3 | 环戊噁草酮 |
1-3 | 丁草胺 |
1-3 | 丙草胺 |
1-3 | 苯噻酰草胺 |
1-3 | 莎稗膦 |
1-3 | 四唑酰草胺 |
1-3 | 异丙甲草胺 |
1-3 | 哌草磷 |
1-3 | 砜吡草唑 |
1-3 | 西草净 |
1-3 | 扑草净 |
1-3 | 胺唑草酮 |
1-3 | 异丙隆 |
1-3 | 除草定 |
1-3 | 哒草特 |
1-3 | 绿麦隆 |
1-3 | 灭草松 |
1-3 | 敌稗 |
1-3 | 嗪草酮 |
1-3 | 莠去津 |
1-3 | 溴苯腈 |
1-3 | 辛酰溴苯腈 |
1-3 | 特丁津 |
1-3 | 异噁草松 |
1-3 | 噁嗪草酮 |
1-3 | 环庚草醚 |
1-3 | 茚草酮 |
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:其中,X代表O、S、SO、SO 2或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;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;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;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;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 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 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 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 21分别独立地代表氢、烷基、烯基、炔基、环烷基、环烷基烷基;R 22分别独立地代表烷基、烯基、炔基、环烷基、环烷基烷基;m代表0或1,n、r分别独立地代表0、1或2;当X代表S、SO时,Y不为甲基。
- 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,X代表O、S、SO、SO 2或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;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;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;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 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 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 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 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 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;m代表0或1,n、r分别独立地代表0、1或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;R’分别独立地代表氢,硝基,羟基,氨基,含有或不含有卤素的烷基、烯基、炔基、环烷基、环烯基、环烷基烷基、烷氧基、烯基氧基、炔基氧基、环烷基氧基、烷氧基烷基、烷氧基羰基、烷硫基羰基、烷基磺酰基、烷基磺酰基烷基、烷基羰基、烷基羰基烷基、烷基酰氧基、烷基氨基、烷基氨基羰基、烷氧基氨基羰基、烷氧基羰基烷基、烷氨基羰基烷基、三烷基甲硅烷基、二烷基膦酰基;R”分别独立地代表氢,含有或不含有卤素的烷基、烯基、炔基、环烷基或环烷基烷基。
- 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,X代表O、S、SO、SO 2或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;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;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;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 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 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 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 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 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;m代表0或1,n、r分别独立地代表0、1或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;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”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。
- 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,X代表O、S、SO、SO 2或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;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;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;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 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 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 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 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 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;m代表0或1,n、r分别独立地代表0、1或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;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”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。
- 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,X代表S、SO或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;Z代表氢,C1-C8烷基;M代表氢,C1-C8烷氧基羰基氧基C1-C8烷基;优选地,X代表S、SO或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;Z代表氢,C1-C6烷基;M代表氢,C1-C6烷氧基羰基氧基C1-C6烷基。
- 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)当通式I中X代表Q时,其制备方法包括以下步骤: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:其中,Q代表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℃;或者,b)当通式I中X代表S时,其制备方法包括如下步骤: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:其中,Hal代表卤素,优选氟、氯或溴;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℃;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: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:或者,d)当通式I中M不为氢时,其制备方法包括如下步骤: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: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℃。
- 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)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;b)ACCase抑制剂:氰氟草酯、噁唑酰草胺;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;d)细胞***抑制剂:二甲戊灵、仲丁灵;e)脂类合成(非ACC)抑制剂:禾草丹、禾草敌;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;g)PDS抑制剂:吡氟酰草胺、氟咯草酮、氟丁酰草胺;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;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;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;k)DOXP抑制剂:异噁草松;l)其他:噁嗪草酮、环庚草醚、茚草酮。
- 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。
- 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。
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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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WO2023208866A1 (en) | 2022-04-25 | 2023-11-02 | Syngenta Crop Protection Ag | Herbicidal compositions |
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WO2024041925A1 (de) * | 2022-08-25 | 2024-02-29 | Bayer Aktiengesellschaft | Herbizide zusammensetzungen |
WO2024041926A1 (de) * | 2022-08-25 | 2024-02-29 | Bayer Aktiengesellschaft | Herbizide zusammensetzungen |
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