US 12,304,890 B2
R-type pyridyloxycarboxylic acid, salt and ester derivative thereof, and preparation method therefor, and herbicidal composition and application thereof
Lei Lian, Qingdao (CN); Xuegang Peng, Qingdao (CN); Rongbao Hua, Qingdao (CN); Jingyuan Zhang, Qingdao (CN); and Qi Cui, Qingdao (CN)
Assigned to Qingdao Kingagroot Chemical Compound Co., Ltd., Qingdao (CN)
Appl. No. 17/414,443
Filed by Qingdao Kingagroot Chemical Compound Co., Ltd., Qingdao (CN)
PCT Filed Dec. 20, 2019, PCT No. PCT/CN2019/126798
§ 371(c)(1), (2) Date Jun. 16, 2021,
PCT Pub. No. WO2020/135235, PCT Pub. Date Jul. 2, 2020.
Claims priority of application No. 201811613197.0 (CN), filed on Dec. 27, 2018.
Prior Publication US 2022/0098153 A1, Mar. 31, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 213/73 (2006.01); A01N 25/32 (2006.01); A01N 43/40 (2006.01); A01N 43/54 (2006.01); A01N 43/56 (2006.01); A01N 43/78 (2006.01); A01N 47/06 (2006.01); A01P 13/00 (2006.01); C07D 213/75 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 417/12 (2006.01)
CPC C07D 213/73 (2013.01) [A01N 25/32 (2013.01); A01N 43/40 (2013.01); A01N 43/54 (2013.01); A01N 43/56 (2013.01); A01N 43/78 (2013.01); A01N 47/06 (2013.01); A01P 13/00 (2021.08); C07D 213/75 (2013.01); C07D 401/12 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 417/12 (2013.01)] 19 Claims
 
1. An ester derivative of R-pyridyloxycarboxylic acid represented by formula I-1,

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wherein the ester derivative of R-pyridyloxycarboxylic acid has an R configuration at the C* atom;
wherein: A and B each independently represent halogen; or alkyl or cycloalkyl optionally substituted with halogen;
C represents hydrogen, halogen, alkyl or haloalkyl;
Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl; alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylaminoalkyl or alkoxyalkyl optionally substituted with halogen; or unsubstituted or substituted aryl, heteroaryl, arylalkyl, heteroarylalkyl;
Y represents nitro or NR1R2,
wherein R1 represents H; alkyl, alkenyl or alkynyl optionally substituted by 1-2 R11; —COR12, nitro, OR13, SO2R14, NR15R16, N═CR17R18, alkylcarbamoyl, dialkylcarbamoyl, trialkylsilyl or dialkylphosphono;
wherein R2 represents H; alkyl optionally substituted by 1-2 R11; or —COR12; or
wherein NR1R2 represents N═CR21NR22R23, N═CR24OR25; or a 5- or 6-membered saturated or unsaturated ring optionally substituted with oxygen atom, sulfur atom, or additional nitrogen atom, which is unsubstituted or substituted by 1-2 groups independently selected from the group consisting of halogen, alkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, and alkoxycarbonyl;
wherein R11 independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl; or unsubstituted or substituted aryl, heteroaryl;
R12 represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy;
R13 represents H, alkyl, haloalkyl, phenyl, benzyl or CHR31C(O)OR32; R31 represents H, alkyl or alkoxy; R32 represents H, alkyl or benzyl;
R14 represents alkyl or haloalkyl;
R15 represents H, alkyl, formyl, alkylacyl, haloalkylacyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R16 represents H or alkyl;
R17 represents H, alkyl; or phenyl that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, alkyl, and alkoxy; R18 represents H or alkyl; or N═CR17R18 represents

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R21 and R24 each independently represent H or alkyl;
R22 and R23 each independently represent H or alkyl; or NR22R23 represents a 5- or 6-membered saturated or unsaturated ring with or without oxygen atom, sulfur atom, or additional nitrogen atom;
R25 represents alkyl;
X represents O or S;
M represents alkyl substituted with halogen, alkenyl optionally substituted with halogen, alkynyl optionally substituted with halogen, cycloalkyl optionally substituted with halogen, cycloalkylalkyl optionally substituted with halogen, -alkyl-Z optionally substituted with halogen,

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optionally substituted with halogen,

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optionally substituted with halogen,

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optionally substituted with halogen,

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optionally substituted with halogen,

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optionally substituted with halogen,

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optionally substituted with halogen; or unsubstituted or substituted heterocyclyl, aryl, heteroaryl;
Z represents

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cyano, nitro, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl;
R3 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl;
R4, R5, and R6 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl.