N-arylsulfonamide and pyrrolidinecarboxylic acid intermediates, and their use for the preparation of herbicidal 1,3-dioxo-1h-pyrrolo[1,2-c]imidazole derivatives

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C2-C4 alkoxyalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C2-C6 haloalkoxyalkyl;
• R2 is H, C1-C4 alkyl;
• C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C2-C6 cyanoalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C1-C4 haloalkyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C3-C4 alkenyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C3-C4 alkynyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C2-C4 alkoxyalkyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C2-C4 alkylcarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is C2-C4 alkoxycarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3 is H then R4 is F or Cl and when R3 is OH then R4 is H.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H;
• and
• R4 is F or Cl.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H;
• and
• R4 is F.

A compound of Formula 3,

• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloaklkyl, C2-C4 alkoxyalkyl;
• C2-C6 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H;
• and
• R4 is Cl.

A process for preparing a compound of Formula 3

• comprising a reaction of a compound of Formula 5
• with a compound of Formula 4
• wherein
• X is H, F or Cl;
• Y is F or Cl;
• R1 is C1-C3 haloalkyl, C2-C4 alkoxyalkyl C2-C4 haloalkoxyalkyl or C2-C6 cyanoalkyl;
• R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• R3 is H or OH;
• and
• R4 is H, F or Cl;
• provided that when R3is H then R4 is F or Cl and when R3 is OH then R4 is H.