IP Library › Granted Patent US 6,884,903

Granted Patent B2

US 6,884,903 · App. 10/387,649 · Granted Apr 26, 2005

Substituted sulfonylaminomethylbenzoic acid (derivatives) and their preparation

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Quick Facts

Patent No.: US 6,884,903
App. No.: 10/387,649
Granted: Apr 26, 2005
Kind: B2

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Abstract

The present invention relates to a compound of the formula (I) The compound according to the invention is suitable for the preparation of herbicidal active substances such as sulfonylureas.

Claims (224)

1. A compound of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di-(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 , which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

R 8 radicals are identical or different and are (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, [(C 1 -C 4 )alkyl]carbonyl or [(C 1 -C 4 )alkoxy]carbonyl which are unsubstituted or substituted, or R 8 is halogen, NO 2 or CN,

n is 0, 1, 2 or 3, and

wherein, the substituents are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido(C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy.

2. A process for preparing a phenylsulfonylurea of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

R 8 radicals are identical or different and are (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, [(C 1 -C 4 alkyl]carbonyl or [(C 1 -C 4 )alkoxy]carbonyl which are unsubstituted or substituted, or R 8 is halogen, NO 2 or CN, and

n is 0, 1, 2 or 3,

R x , R y independently of one another are a hydrogen atom, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio, or are mono- or di[(C 1 -C 4 )alkyl]amino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )alkenyloxy or (C 3 -C 6 )alkynyloxy, and

X is CH or N

and wherein, unless otherwise identified, the substituents are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido (C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy;

which comprises:

a) reacting a compound of formula (VI) according to claim 1 with a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

which R 2 , R 3 , and R 6 are hydrogen

b) reacting the compound of formula (I) with an alkylating agent or by reductive animation to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alkyl group

c) first reacting the compound formed in step b) with a diazotizing agent in the presence of an acid followed by an SO 2 source in the presence of a copper catalyst and an acid to give a compound of the formula

where Y is halogen

d) reacting the compound of formula (VII) with either:

i) amine of the formula (XII) in the presence of MOCN, wherein M is an ammonium ion or an alkali metal ion, to give a compound of the formula (XIII)

ii) ammonia in the presence of a suitable solvent to give a compound

and subsequently preparing the compound of the formula (XIII) by:

a) reacting the compound of the formula (VIII) with a compound of the formula (IX) to give the compound of the formula (XII)

b) reacting the compound of the formula (VIII) with an isocyanate of the formula (X) to give the compound of the formula (XIII)

c) reacting the compound of the formula (VIII) with an alkyl isocyanate and phosgene to give a compound of the formula (XI)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

d) reacting the compound of the formula (VIII) with a carbonic acid derivative R—CO—OPh, in which Ph=unsubstituted or substituted phenyl and R=halogen or unsubstituted or substituted phenoxy to give a compound of the formula (XIV)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

where R 1 , R 7 , R 8 , and n in formulae (XI) and (XIV) are as defined in formula (I) R x , R y and X in formulae (IX), (X) and (XII) are as defined in formula (XIII) of the present claim and Ph in formulae (IX) and (XIV) is unsubstituted or substituted phenyl, wherein the substituents on the phenyl ring are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido (C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy.

3. A process of preparing a sulfonylurea of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

X is CH or N

which comprises:

a) reacting a compound of the formulae

with either a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

b) reacting the compound of formula (III) or (IIIa) with a sulfonic acid derivative to give a compound of the formula

which R 1 , R 2 , and R 6 are hydrogen

c) reacting the compound of formula (I) with an alkylating agent or by reductive animation to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alkyl group

d) first reacting the compound formed in step c) with a diazotizing agent in the presence of an acid followed by an SO 2 source in the presence of a copper catalyst and an acid to give a compound of the formula

where Y is halogen

e) reacting the compound of formula (VII) with either:

i) amine of the formula (XII) in the presence of MOCN, wherein M is an ammonium ion or an alkali metal ion, to give a compound of the formula (XIII)

ii) ammonia in the presence of a suitable solvent to give a compound

and subsequently preparing the compound of the formula (XIII) by

a) reacting the compound of the formula (VIII) with a compound of the formula (IX) to give the compound of the formula (XIII)

b) reacting the compound of the formula (VIII) with an isocyanate of the formula (X) to give the compound of the formula (XIII)

c) reacting the compound of the formula (VIII) with an alkyl isocyanate and phosgene to give a compound of the formula (XI)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

where R 1 , R 7 , R 8 , and n in formulae (XI) and (XIV) are as defined in formula (1) R x , R y and X in formulae (IX), (X) and (XII) are as defined in formula (XIII) of the present claim and Ph in formulae (IX) and (XIV) is unsubstituted or substituted phenyl, wherein the substituents on the phenyl ring are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido (C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 3 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy.

4. A process for preparing a phenylsulfonylurea of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2

R 8 radicals are identical or different and are (C 1 -C 4 alkyl, (C 1 -C 4 )alkoxy, [(C 1 -C 4 )alkyl]carbonyl or [(C 1 -C 4 )alkoxy]carbonyl which are unsubstituted or substituted, or R 8 is halogen, NO 2 or CN, and

n is 0,1 , 2 or 3,

R x , R y independently of one another are a hydrogen atom, halogen, (C 1 -C 4 alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio, or are mono- or di[(C 1 -C 4 )alkyl]amino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )alkenyloxy or (C 3 -C 6 )alkynyloxy, and

X is CH or N

which comprises:

a) reacting a compound of formula

with a sulfonic acid derivative to give a compound of the formula

and reacting the compound of the formula (VI) with a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

which R 2 , R 3 , and R 6 are hydrogen

b) reacting the compound of formula (I) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alky group

where Y is halogen

d) reacting the compound of formula (VII) with either:

i) amine of the formula (XII) in the presence of MOCN, wherein M is an ammonium ion or an alkali metal ion, to give a compound of the formula (XIII)

ii) ammonia in the presence of a suitable solvent to give a compound

and subsequently preparing the compound of the formula (XIII) by:

a) reacting the compound of the formula (VIII) with a compound of the formula (IX) to give the compound of the formula (XIII)

b) reacting the compound of the formula (VIII) with an isocyanate of the formula (X) to give the compound of the formula (XIII)

c) reacting the compound of the formula (VIII) with an alkyl isocyanate and phosgene to give a compound of the formula (XI)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

where R 1 , R 7 , R 8 , and n in formulae (XI) and (XIV) are as defined in formula (I), R x , R y and X in formulae (IX), (X) and (XII) are as defined in formula (XIII) of the present claim and Ph in formulae (IX) and (XIV) is unsubstituted or substituted phenyl, wherein the substituents on the phenyl ring are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido (C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy.

5. A process for preparing a phenylsulfonylurea of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 form chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

X is CH or N

which comprises:

a) reacting a compound of the formulae

with either a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

b) reacting the compound of formula (III) or (IIIa) with a sulfonic acid derivative to give a compound of the formula

which R 1 , R 2 , and R 6 are hydrogen

c) reacting the compound of formula (I) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alkyl group

where Y is halogen

e) reacting the compound of formula (VII) with either:

i) amine of the formula (XII) in the presence of MOCN, wherein M is an ammonium ion or an alkali metal ion, to give a compound of the formula (XIII)

ii) ammonia in the presence of a suitable solvent to give a compound

and subsequently preparing the compound of the formula (XIII) by

a) reacting the compound of the formula (VIII) with a compound of the formula (IX) to give the compound of the formula (XIII)

b) reacting the compound of the formula (VIII) with an isocyanate of the formula (X) to give the compound of the formula (XIII)

c) reacting the compound of the formula (VIII) with an alkyl isocyanate and phosgene to give a compound of the formula (XI)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

where R 1 , R 7 , R 8 , and n in formulae (XI) and (XIV) are as defined in formula (1) R x , R y and X in formulae (IX), (X) and (XII) are as defined in formula (XIII) of the present claim and Ph in formulae (IX) and (XIV) is unsubstituted or substituted phenyl, wherein the substituents on the phenyl ring are halogen, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkoxy, (C 1 -C 8 )alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido (C 1 -C 8 )alkoxycarbonyl, (C 1 -C 8 )alkylcarbonyl, formyl, carbamoyl, mono- and di-(C 1 -C 8 )alkylaminocarbonyl, acylamino, mono- and di-(C 1 -C 8 )alkylamino, (C 1 -C 8 )alkylsulfinyl, (C 1 -C 8 )haloalkylsulfinyl, (C 1 -C 8 )alkylsulfonyl, halo(C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )cycloalkyl, (C 1 -C 8 )cycloalkenyl, wherein the cycloalkyl and cycloalkyl radicals are optionally substituted by (C 1 -C 8 )alkyl and halo(C 1 -C 8 )alkyl, (C 1 -C 8 )alkenyl, (C 1 -C 8 )alkynyl, (C 1 -C 8 )alkenyloxy or (C 1 -C 8 )alkynyloxy.

6. A process of preparing a sulfonylurea of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 )mEm1- which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

X is CH or N

which comprises:

a) reacting a compound of the formulae

with either a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

b) reacting the compound of formula (III) or (IIIa) with a sulfonic acid derivative to give a compound of the formula

which R 1 , R 2 , and R 6 are hydrogen

c) reacting the compound of formula (I) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alkyl group

where Y is halogen

e) reacting the compound of formula (VII) with either:

i) amine of the formula (XII) in the presence of MOCN, wherein M is an ammonium ion or an alkali metal ion, to give a compound of the formula (XIII)

ii) ammonia in the presence of a suitable solvent to give a compound

and subsequently preparing the compound of the formula (XIII) by

a) reacting the compound of the formula (VIII) with a compound of the formula (IX) to give the compound of the formula (XIII)

b) reacting the compound of the formula (VIII) with an isocyanate of the formula (X) to give the compound of the formula (XIII)

c) reacting the compound of the formula (VIII) with an alkyl isocyanate and phosgene to give a compound of the formula (XI)

which is subsequently reacted with an amine of the formula (XII) to give the compound of the formula (XIII)

7. A process for preparing a compound of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 2 , R 3 independently of one another are H or acyl,

R 4 , R 5 are H,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

which comprises

a) reacting a compound of the formulae

with either a reagent that reduces a nitro group to an amine or by catalytic hydrogenation to give a compound of the formula

and

b) reacting the compound of formula (III) or (IIIa) with a sulfonic acid derivative to give a compound of the formula (I), wherein R 1 , R 2 , and R 6 are hydrogen, and

c) optionally reacting a compound formed in b) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 an unsubstituted or substituted C 1 -C 8 -alkyl group.

8. A process for preparing a compound of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 2 , R 3 independently of one another are H or acyl,

R 4 , R 5 are H,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 ) m E m 1 — which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

which comprises

a) reacting a compound of the formulae

with a sulfonic acid derivative to give a compound of the formula

and reacting the compound of formula (VI) with an agent which reduces a nitro compound to an amine or by catalytic hydrogenation to give a compound of formula (I), wherein R 1 , R 2 , and R 6 are hydrogen, and

b) optionally reacting a compound of formula (I) formed in a) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 an unsubstituted or substituted C 1 -C 8 -alkyl group.

9. A process for preparing a compound of the formula

in which

R 1 is H, (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl or (C 3 -C 8 )alkynyl, where the last 3 radicals are unsubstituted or substituted,

R 2 , R 3 independently of one another are H or acyl,

R 4 , R 5 are H,

R 6 is H or (C 1 -C 8 )alkyl which is unsubstituted or substituted,

R 7 is (C 1 -C 8 )alkyl, (C 3 -C 8 )alkenyl, (C 3 -C 8 )alkynyl, (C 6 -C 14 )aryl or mono- or di(C 1 -C 8 )alkylamino which are unsubstituted or substituted, or

R 6 and R 7 together form a chain of the formula —(CH 2 )mEm1- which is unsubstituted or substituted, and where m=2, 3 or 4, m 1 =0 or 1 and E=CO or SO 2 ,

n is 0, 1, 2 or 3,

which comprises

a) reacting the compound of formula (III) or (IIIa)

with a sulfonic acid derivative to give a compound of the formula (I), wherein R 1 , R 2 , and R 6 are hydrogen, and

and

b) optionally reacting a compound formed in a) with an alkylating agent or by reductive amination to give a compound of the formula (I) where R 6 is an unsubstituted or substituted C 1 -C 8 -alkyl group.

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 034914/0354 →

CHANGE OF NAME Recorded Nov 12, 2008

From: BAYER CROPSCIENCE GMBH

To: BAYER CROPSCIENCE AG

Reel/Frame 021838/0869 →

CHANGE OF NAME Recorded Nov 12, 2008

From: AVENTIS CROPSCIENCE GMBH

To: BAYER CROPSCIENCE GMBH

Reel/Frame 021924/0762 →