C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/251, 260/249
C07D 239/28 (2006.01) A01N 47/36 (2006.01) C07D 251/12 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1226862
Title HERBICIDAL SULFONAMIDES Abstract Sulfonamides, agriculturally suitable salts thereof and herbicidal compositions containing them are useful as preemergent and postemergent herbicides and as plant growth regulants. Such sulfonamides are of the formula: Image and agricultrually suitable salts thereof, characterized in that: J is NHR2, NR3R4 or NR?NR?R?: W is O or S; R is H or CH3; R1 is H, C1 to C3 alkyl, C1 to C3 haloalkyl, halo- gen, nitro, C1 to C3 alkoxy, SO2NRaRB, C1 to C3 alkylthio, C1 to C3 alkylsulfinyl, C1 to C3 alkylsulfonyl, CN, CO2Rc, C1 to C3 haloalkoxy. C1 to C3 haloalkylthio, C2 to C3 alkoxyalkyl. C2 to C3 haloalkoxyalkyl, C2 to C3 alkylthio- alkyl, C2 to C3 haloalkylthioalkyl, C2 to C3 cyanoalkl or NRdRe: Ra is H, C1 to C4 alkyl, C2 to C3 cyanoalkyl, methoxy or ethoxy; Rb is H, C1 to C4 alkyl or C3 to C4 alkenyl; or Ra and Rb can be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-; Rc is C1 to C4 alkyl, C3 to C4 alkenyl, C3 to C4 alkynyl, C2 to C4 haloalkyl, C2 to C3 cyano- alkyl, C5 to C6 cycloalkyl, C4 to C7 cyclo- alkylalkyl or C2 to C4 alkoxyalkyl; Rd and Re are independently H or C1 to C2 alkyl; 2 R2 is C5 to C6 alkyl, C5 to C6 alkenyl, C2 to C6 haloalkenyl, C3 to C6 alkynyl, C3 to C6 cyclo- alkyl, C3 to C6 cycloalkyl optionally substi- tuted with 1 or 2 CH3 groups, C4 to C7 cyclo- alkylalkyl, C5 to C6 cycloalkenyl, C3 to C6 epoxyalkyl, C2 to C6 haloalkyl. CH2CH2(OR5)2, Image (CH2)3OCH3, phenyl which can be optionally substituted with R7, Image CH2C(O)CH3, CN, OR6, C1 to C6 alkyl substi- tuted with OR9, S(O)nR10 or NR11R12, Q,CHR8Q or CH2CH2Q; R3 is C1 to C6 alkyl, C3 to C6 alkenyl, C3 to C6 alkynyl, C3 to C6 cycloalkyl which can be optionally substituted with 1 or 2 CH3 groups, C4 to C7 cycloalkylalkyl, C5 to C6 cyclo- alkenyl, C1 to C6 haloalkyl, C1 to C5 alkoxy, C3 to C6 epoxyalkyl or C1 to C6 alkyl substi- tuted with OR9, S(O)nR10, NR11R12 or P(O)(OR5)2: R4 is C1 to C3 alkyl substituted with 1 to 3 atoms of F, Cl or Br, C3 to C4 alkynyl, CH2CH2(OR5)2, Image ,C2 to C6 haloalkenyl, C3 to C6 epoxyalkyl, CH2C(O)CH3, CN, C1 to C6 alkyl substituted with OR9, S(O)nR10 or NR11Rl2, Q, CHR8Q or CH2CH2Q; R3 and R4 can be taken together with the sulfon- amide nitrogen to form a saturated 5- or 6 membered ring substisuted by one or more groups selected from L or a partially saturated 5- or 6-membered ring optionally substituted by one or more groups selected from L; 3 R5 is C1 to C3 alkyl: R6 is C1 to C5 alkyl; R7 is H, C1 to C3 alkyl, halogen. NO2, CF3, CN or C1 to C3 alkoxy; R8 is H or CH3; R9 is H, SO2R5, C(O)R5, CO2R5, C(O)NR11R12 or P(O)(OR5)2; R10 is C1 to C3 alkyl; R11 is H or C1 to C3 alkyl; R12 is H or C1 to C3 alkyl; m is 2 or 3; n is 0, 1 or 2; R'2, R'3 and R'4 are independently H, C1 to C4 alkyl, C3 to C4 alkenyl, C3 to C4 alkynyl, C1 to C4 haloalkyl. C(O)R'5. CO2R'6, C(O)NR'7R'8, C(S)NR'7R'8, Q, CHRQ, CH2CH2Q, C2 to C3 alkyl substituted with OR'9, phenyl which can be optionally sub- stituted with R'10 and R'11 or Image : R3 and R4 can be taken together to form -(CH2)4-, -(CH2)5-. CH2CH2OCH2CH2, CH=CHCH=CH, CH=N-N=CH or Image R'5 is C1 to C3 alkyl or phenyl which can be op- tionally substituted with R'10 and R'11; R'6 is C1 to C3 alkyl: R'7 and R'8 are independently H or C1 to C3 alkyl; R'9 is H, SO2R'6. C(O)R'6, CO2R'6, C(O)NR'7R'8, C1 to C3 alkyl, C1 to C3 haloalkyl or P(O)(OR'6)2; R'10 and R'11 are independently H, C1 to C3 alkyl, Cl, F, Br, NO2, CF3, CN or C1 to C3 alkoxy; R'12 and R'13 are independently H, C1 to C3 alkyl. phenyl which can optlonally substituted with R'10 and R'11 or Image 4 R? and R? can be taken together to form -(CH2)4- or -(CH2)5-: Q is a saturated 5- or 6-membered ring which is bonded through a carbon atom and contains 1 heteroatom selected from oxygen. sulfur, or nitrogen or an unsaturated or partially unsat- urated 5- or 6-membered ring which is bonded through a carbon atom and containg 1 to 3 heteroatoms selected from 1 sulfur, 1 oxygen or 1 to 3 nitrogen; and Q can be optionally substituted by one or more groups selected from L; L is C1 to C4 alkyl, C1 to C3 haloalkyl, halogen, C1 to C3 alkoxy, C1 to C3 alkylthio. C3 to C4 alkenyloxy, C3 to C4 alkenylthio, C1 to C2 haloalkoxy or C1 to C2 haloalkylthio; A is Image , Image , Image , A-1 A-2 A-3 Image , Image , Image : A-4 A-5 A-6 X is H, C1 to C4 alkyl, C1 to C4 alkoxy, C1 to C4 haloalkoxy, C1 to C4 haloalkyl, C1 to C4 halo- alkylthio, C1 to C4 alkylthio, halogon, C2 to C5 alkoxyalkyl, C2 to C5 alkoxyalkoxy, amino, C1 to C3 alkylamino or di(C1 to C3 alkyl)- amino; 5 Y is H, C1 to C4 alkyl, C1 to C4 alkoxy, C1 to C4 haloalkoxy, C1 to C4 haloalkylthio, C1 to C4 alkylthio, C2 to C5 alkoxyalkyl, C2 to C5 alkoxyalkoxy, amino, C1 to C3 alkylamino, di(C1 to C3 alkyl)amino, C3 to C4 alkenyl- oxy, C3 to C4 alkynyloxy, C2 to C5 alkyl- thioalkyl, C1 to C4 haloalkyl, C3 to C5 cycloalkyl, C2 to C4 alkynyl, C(O)Rf, Image or N(OCH3)CH3; m is 2 or 3: L1 and L2 are independently O or S; Rf is H or CH3: Rg and Rh are independently C1 to C2 alkyl; Z is CH or N: Y1 is O or CH2: X1 is CH3, OCH3, OC2H5 or OCF2H: Y2 is H or CH3: X2 is CH3, OCH3 OR SCH3: Y3 is CH3, CH2CH3 or CH2CF3: and X3 is CH3 or OCH3: characterized further in that: a) when X is Cl, F, Br or I, then Z is CH and Y is OCH3, OC2H5, N(OCH3)CH3, NHCH3 or N(CH3)2; b) when X or Y is OCF2H, then Z is CH; c) the total number of carbon atoms in R'2, R'3 and R'4 does not exceed 10; d) when A is A-5, then J is NR'2NR'3R'4; e) when R2 is CH2CF3 and A is A-1, then one of both of X and Y is OCF2H; f) when R3 or R4 is CH2CF3, then the other is CHF2, CH2CH2F, CH2CH2Cl, CH2CH2Br or CH2CF3: g) when R4 is CF2H, then R3 is other than C1 to C3 alkyl; h) when R4 is C3 to C4 alkynyl, then R3 is CHF2, CH2CH2F, CH2CH2Cl, CH2CH2Br or C3 to C4 alkynyl; i) when one or both of X and Y is OCF2H, then R6 is C3 to C5 alkyl; and j) when R2 is OR6 and A is A-1 wherein Z is CH, then one or both of X and Y is other than C1 to C4 alkyl.
502068
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
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