Herbicidal n-hydroxy-n'-sulfonylguanidines

C - Chemistry – Metallurgy – 07 – D

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260/249, 260/251

C07D 239/28 (2006.01) C07D 251/12 (2006.01) C07D 403/12 (2006.01)

Patent

CA 1255661

ABSTRACT OF THE DISCLOSURE The present application disclosed plant growth regulants and herbicides of the following formula: Image wherein R'' is C1-C3 alkyl; R is H or CH3; L is Image L-1 L-2 L-3 Image L-4 L-5 L-6 Image L-7 L-8 Image L-9 L-10 L-11 - 2 - Image L-12 L-13 L-14 Image L-15 L-16 L-17 R5 is C1-C4 alkyl, C1-4 alkoxy, OCH2CH2OCH3. F, C1, Br, NO, CF3, CO2R19, SO2NR20R21. SO2N(OCH3)CH3, OSO2R22, S(O)nR23, WCF3, WCH2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, Image - 3 - R6 is H, F, C1, Br,CF3, CH3, OCH3, SCH3 or OCF2H; R7 is H. CH3, OCH3, F, C1, Br. SO2N(CH3)2, OSO2CH3 or S(O)nCH3: R8 is CH3, CH2CH3, OCH3, OCH2CH3, F, C1, Br, SO2NR20R21, SO2N9OCH3) or S(O)nR23; R9 is C1-C3 alkyl, F, C1, Br, NO2. CO2R19 SO2NR20R2l, SO2N(OCH)3 CH3 or S(O)n23; R10 is C1, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or CH3 or CH2CH3 R11 is H, CH3 or CH2CH3; R12 is H, CH3 or CH2CH3; R13 is H or CH3; R14 is H or CH3; R15 is H or CH3; R16 is CH3 or CH2CH3; R17 is H or C1-C4 alkyl; R18 is H or CH3; R19 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2C1 or CH2CH=CH2; R20 is C1-C3 alkyl; R21 is C1-C3 alkyl; R22 is C1-C3 alkyl or N(CH3)2; R23 is C1-C3 alkyl or CH2CH=H2; m is 0 or 1; n is 0 or 2; Q1 is O. S. SO2 or NR17; Q2 is O, S or NR17; and W is O. S or SO2; A is Image A-1 A-2 A-3 - 4 - Image A-4 A-5 A-6 X is CH3, OCH3, OCH2CH3, C1, F. Br, OCF2H, CH2F or CF3; Y is H, CH3, OCH3, OCH2CH3, CH2OCH3, CH2OCH2CH3, N(CH3)2, CH2CH3, CF3, SCH, OCH2CH=CH2, OCH2C?CH, OCH2CF3, OCH2CH2OCH3, CH2SCH3, OCF2H, SCF2H, CR24 (QCH3)2, Image , Image , Image or CR24 (QCH2CH3)2; Q is O or S; R24 is H or CH3; Z is CH or N; Y1 is CH2 or O; X1 is CH3, OCH3, OCH2CH3 or OCF2H; Y2 is H or CH3; X2 is CH3, CH2CH3 or CH2CF3; Y3 is OCH3, OCH2CH3, SCH3, CH3 or CH2CH3; X3 is CH3 or CH3; and their agriculturally suitable salts; provided that 1) when L is L-1 and A is A-1, R5 is C2-C4 alky1, C2 -C4 alkoxy, OCH2CH2OCH3, OSO2R22, S(O)nR23, WCF2, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, Image , - 5 - Image 2) when L is L-1 and A is A-2 or A-3, then R5 is C1-C4 alkyl, C2-C4 alkoxy, OCH2CH2OCH3, Br, OSO2R22, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H5, Image Image 3) when L is L-3 and A is A-1, A-2 or A-3, then R8 is SO2NR20R21, SO2N(OCH3)CH3 or SO2R23; 4) when L is L-4, L-5 or L-6 and A is A-1, A-2 and A-3, then R9 is C1-C3 alkyl, F, Cl, Br, NO2, SO2NR20R21, SO2N(OCH3)CH3 or S(O)nR23; and 5) when L is L2 then A is A5 or A6; - 6 - 6) the total number of carbon atoms of R20 and R21 is less than or equal to four; 7) when M is 1, then R13 is H; 8) when L is L-19, then R17 and R18 are not simultaneously H; and 9) when X is Cl, F or Br, then Z is CH and Y is OCH3; OCH3CH3, N(CH3)2 or OCF2H.

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