C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/249, 260/251
C07D 491/048 (2006.01) A01N 47/36 (2006.01) C07D 491/04 (2006.01) C07D 495/04 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1227796
Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure Sulfonamides, useful as herbicides and plant growth regulants, are disclosed. The sulfonamides are of the formula: Image wherein Image Ia Ib Ic E is a bridge of 3 or 4 atoms, which may be sub- stituted or unsubstituted, containing 0-2 heteroatoms selected from the group consist- ing of oxygen, sulfur and nitrogen, and also containing 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a partially saturated 5- or 6-membered carbocyclic or heterocyclic ring: or E is a bridge of 3 or 4 atoms, which may be substi- tuted or unsubstituted, containing 0-1 heter- oatoms selected from oxygen or sulfur, 0-2 heteroatoms of nitrogen and 1-4 atoms of carbon, said bridge together with two carbon attachment sites forming a fully unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, they must be separated by at least one atom of carbon, and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO2; in the bridging group E, sulfur may take the form of S, SO or SO2, and one of the atoms of carbon may be a carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof: when one of the bridging atoms is a substituted carbon, the substituent on said carbon includes H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, C1-C3 alkoxycar- bonyl, CN, NO2, OH, C1-C3 alkoxy, C1-C3 halo- alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylcarbonyl, C1-C3 alkylsulfamoyl, di(C1-C3 alkyl)sulfamoyl and C1-C2 alkyl substituted with C1-C2 alkoxy, C1-C2 alkylthio or CN; when the bridging atom is nitrogen (other than nitrogen in the form of a cyclic sulfonamide), substituents on said nitrogen include H, C1-C4 alkyl, C1-C4 halo- alkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, C1-C3 alkoxy, C1-C4 alkylcarbonyl, C1-C3 alkoxycarbonyl, C1-C3 alkylaminocarbonyl or C1-C4 alkylsul- fonyl; when the bridging atom is nitrogen in the form of a cyclic sulfonamide , then the nitrogen is substituted by R6 as defined below: W is O or S: R is H or CH3: n is 0 or 1; R1 is H, CH3, OCH3 or Cl; R2 is H, C1-C3 alkyl, Cl, Br, P, C1-C3 alkoxy C1-C3 alkylthio, CF3, CH2OCH3, CH2SCH3 or CH2CN: R3 is H, C1-C3 alkyl, halogen, C1-C3 alkoxy C1-C3 alkylthio, C1-C2 alkylsulfonyl, C1-C2 alkylcarbonyl, C1-C2 alkoxycarbonyl, C3-C4 alkenyl, NO2, NH2, C1-C2 alkylamino, di(C1-C2)- alkylamino, C1-C2 alkylsulfamoyl, di(C1-C2)- alkylsulfamoyl, (C1-C2 alkyl)aminocarbonyl, di(C1-C2 alkyl)aminocarbonyl or C3-C4 alkynyl; R6 is H, R?, SR?, SO2R?, OR?, C(O)R8. L, C(O)L. CO2R?, (CO)2OR?. (CO)2R?, C(O)NR9R10. C(O)NRA, C(S)SR?, NH2, NR9R10, OH, CN, P(O)R11R12, P(S)R11R12 or Si(CH3)2R13; R8 is C1-C10 alkyl, C3-C10 alkoxyalkoxyalkyl, C2-C10 alkenyl, C3-C10 epoxyalkyl, C2-C10 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkyl- alkyl or phenyl optionally substituted with R14: when R8 is C3-C6 cycloalkyl or C4-C7 cycloalkyl- alkyl, it may optionally be substituted by C1-C4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R8 is C1-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl, it may optionally be substituted by one or more halogens and/or by (R15)r provided that when r is 2, the values of R15 may be iden- tical or different; R? is C1-C10 alkyl, C3-C10 alkoxyalkoxyalkyl, C3-C10 alkenyl, C3-C10 epoxyalkyl, C3-C10 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkyl- alkyl or phenyl optionally substituted with R14: when R? is C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl, it may optionally be substi- tuted by C1-C4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R9 is C1-C10 alkyl, C3-C10 alkenyl or C3-C10 alkynyl, it may optionally be substi- tuted by one or more halogens and/or by (R15)r provided that when r is 2, the values of R15 may be identical or different; r is 0, 1 or 2: R9 is H or C1-C4 alkyl; R10 is H, C1-C10 alkyl, C1-C10 haloalkyl. C3-C10 alkenyl, C3-C10 alkynyl. C3-C6 cycloalkyl or phenyl substituted with R14; R10 is C1-C10 alkyl. C1-C10 haloalkyl. C3-C10 alkenyl, C3-C10 alkynyl, C3-C6 cycloalkyl or phenyl substituted with R14; R11 and R12 are independently C1-C4 alkyl, C1-C4 alkoxy or C1-C4 alkylthio; R13 is C1-C10 alkyl, benzyl or phenyl optionally substituted with R14: R14 is H, F, Cl. Br. CH3, OCH3. NO2. CN, SCH3, SO2CH3 or CF3: R15 is OR10, OC(O)R10. OC(O)NR9R10. OSO2R?, OP(O)R11R12, OSi(CH3)2R13, SR10, SOR?' SO2R?, SCN. CN. SP(O)R11R12, SP(S)R11R12, P(O)R11R12, P(S)R11R12, NR9R10, N+R9R10R13, NR9C(O)R10, NR9C(O)OR?, NR9C(O)NR9R10, NR9SO2R?, NR9P(O)R11R12, NR9P(S)R11R12. NO2, C(O)R10, C(O)OR10. C(O)NR9R10, C(R10)=NOR12, naphthyl. L. phenyl optionally substituted with R14 and/ or R16, Image R16 is H. F, Cl or Br: L is a 5- or 6-membered aromatic heterocycle, a 5- or 6-membered dihydroaromatic heterocycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms and/or 0-4 nitrogen atoms and these heterocycles may optionally be substituted by 1-4 CH3, 1-2 OCH3, SCH3, Cl, N(CH3)2 or CN groups or L is a 5- or 6-membered lactone. lactam or cycloalkanone which may optionally be substituted by 1-4 CH3 groups: A is Image A-1 A-2 A-3 Image A-4 A-5 A-6 Image A-7 X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo- alkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alkylthio, halogen, C2-C5 alkoxyalkoxy, amino, C1-C3 alkylamino or di(C1-C3 alkyl)- amino; Y is H C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo- alkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio, C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy, amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkylsul- finylalkyl, C1-C4 haloalkyl, C2-C5 alkylsul- fonylalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl, C2-C5 alkylthioalkyl, Image Image or N(OCH3)CH3; W1 and W2 are independently O or S; m is 2 or 3; Ra is H or CH3; Rb is C1-C2 alkyl; Rc is C1-C2 alkyl; Z is CH, N, CCH3, CC2N5, CCl or CBr; Y1 is O or CH2: X1 is CH3, OCH3. OC2H5 or OCF2H; X2 is CH3, C2H5 or CH2CF3: Y2 is OCH3, OC2H5, SCH3, SC2H5, OCF2H, SCF2H, CH or CH2CH3; X3 is CH3, OCH2, OC2H5, CH2OCH3 or Cl; Y3 is H or CH3; X4 is CH3, OCH3, OC2H5 or CH2OCH3 or Cl; Y4 is CH3, OCH3, OC2H5 or Cl; and Z1 is CH or N; and their agriculturally suitable salts: provided that a) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH3, OCH3, OC2H5, CH2OCH3. C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCN2CH2OCH3, CH(OCH3)2 or Image b) when X is Cl, Br, F or I, then Z is CH and Y is OCH3, OC2N5, NH2, NHCH3, N(CH3)2 or OCF2H; c) when X or Y is C1 haloalkoxy, then Z is CH: d) in compounds of Formula Ia, either R1 or R2 must be H: e) when the total number of carbon atoms in X and Y is greater than 4, then the total number of carbon atoms in R1, R2. R3 and the bridging group E is less than or equal to 10; f) X4 and Y4 are not simultaneously Cl; g) the total number of carbon atoms in R6 is less than or equal to 12; and h) when R15 and the bridging nitrogen of a cyclic sulfonamide are attached to the same carbon then R15 is other than OH, SH, OC(O)R10, OC(O)NR9R10, OSO2R?, OP(O)R11R12, OSi(CH3)2Rl3, SP(O)R11R12, SP(S)R11R12, NR9R10 or N+R9R10R13.
508535
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
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