IP Library › Granted Patent US 7,390,827

Granted Patent B2

US 7,390,827 · App. 11/058,951 · Granted Jun 24, 2008

3-aminocarbonyl substituted benzoylpyrazolones

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Quick Facts

Patent No.: US 7,390,827
App. No.: 11/058,951
Granted: Jun 24, 2008
Kind: B2

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Abstract

A description is given of derivatives of benzoylpyrazoles of the formula (I) and of their use as herbicides. In this formula (I) R 1a , R 1b , R 1c , R 2 , R 3 , R 4 and R 5 stand for various radicals, X for a bridging atom, L for a carbon chain and Y for a chalcogen atom.

Claims (77)

1. A compound of the formula (I) or salt thereof

in which the radical and the indices have the following definitions:

X is O;

L is CH 2 ;

Y is oxygen;

R 1a , R 1b , R 1c independently are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato,

(C 1 -C 6 )-alkyl-CO—O, (C 1 -C 6 )-alkyl-S(O) n —O, (C 1 -C 6 )-alkyl-S(O) m , (C 1 -C 6 )-haloalkyl-S(O) m , (C 3 -C 7 )-cycloalkyl-S(O) m , di-(C 1 -C 6 )-alkyl-N—SO 2 , (C 1 -C 6 )-alkyl-SO 2 —NH, (C 1 -C 6 )-alkyl-NH—CO, di-(C 1 -C 6 )-alkyl-N—CO, (C 1 -C 6 )-alkyl-SO 2 —[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-CO—[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-O—CH 2 , (C 1 -C 6 )-alkyl-S(O) n —CH 2 , (C 1 -C 6 )-alkyl-NH—CH 2 , 1,2,4-triazol-1-yl, 1,2,4-triazol-1-yl-CH 2 ,

or are each (C 1 -C 6 )-alkyl-(Y) p , (C 2 -C 6 )-alkenyl-(Y) p , (C 2 -C 6 )-alkynyl-(Y) p , each of which is substituted by v radicals selected from the group consisting of cyano, nitro and halogen;

R 2 , R 3 independently are each hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-cycloalkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 ) -cycloalkenyl, straight-chain or branched [O—C(R 6 )- 2 ] w —[O—C(R 6 )- 2 ] x —R 6 , (C 1 -C 6 )-alkyl-aryl, (C 2 -C 6 )-alkenyl-aryl, (C 2 -C 6 )-alkynyl-aryl, straight-chain or branched [O—C(R 6 ) 2 ] w —[O—C(R 6 ) 2 ] x -aryl, the last 16 of the abovementioned radicals being substituted by v radicals selected from the group consisting of cyano, nitro and halogen,

or are each aryl, heterocyclyl or heteroaryl each substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl-(Y) p and halo-(C 1 -C 6 )-alkyl-(Y) p ,

R 4 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl, (C 3 -C 9 )-cycloalkyl or (C 3 -C 9 )-halocycloalkyl;

R 5 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-halo-cycloalkyl, or is phenyl substituted by v radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy;

R 6 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, halo-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkoxycarbonyl, halo-(C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, halo-(C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, halo-(C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-alkylsulfonyl, halo-(C 1 -C 6 )-alkylsulfonyl, or is benzyl, benzoyl, benzoylmethyl, phenoxycarbonyl or phenylsulfonyl each of which is substituted by v radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy;

m is 1 or 2;

n is 0, 1 or 2;

p is 0 or 1;

v is 0, 1, 2 or 3;

w and x independently are each 0, 1, 2, 3 or 4;

w and x should not both be zero at the same time.

2. A compound as claimed in claim 1 , wherein R 2 , R 3 independently are each hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-cycloalkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 )-cycloalkenyl, straight-chain or branched [O—C(R 6 ) 2 ] w —[O—C(R 6 )- 2 ] x -R 6 , (C 1 -C 6 )-alkyl-aryl, (C 2 -C 6 )-alkenyl-aryl, (C 2 -C 6 )-alkynyl-aryl, straight-chain or branched [O—-C(R 6 ) 2 ] w —[O—C(R 6 ) 2 ] x -aryl, the last 16 of the abovementioned radicals being substituted by v radicals selected from the group consisting of cyano, nitro, and halogen, or are each

aryl substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl-(Y) p and halo-(C 1 -C 6 )-alkyl-(Y) p .

3. A compound as claimed in claim 1 , wherein Y is oxygen and R 1c is hydrogen.

4. A compound as claimed in claim 1 , wherein

R 1a , R 1b independently are each F, Cl, Br, CH 3 , CH 3 S, CH 3 O, CH 3 SO 2 , C 2 H 5 SO 2 , CF 3 CH 2 SO 2 , cyclopropyl-SO 2 , CF 3 or NO 2 ;

R 2 , R 3 independently are each hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 9 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl, or (C 1 -C 6 ) -alkyl-aryl, the last 6 radicals being substituted by v radicals selected from the group consisting of cyano, nitro, and halogen, or are each aryl, the last radical being substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl-(Y) p and halo-(C 1 -C 6 )-alkyl-(Y) p .

5. A compound as claimed in claim 1 , wherein

R 2 , R 3 independently are each hydrogen or (C 1 -C 6 )-alkyl, and

R 4 is hydrogen, methyl or cyclopropyl.

6. A compound as claimed in claim 1 , wherein

R 6 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylsulfonyl, or is benzoyl or phenylsulfonyl each of which is substituted by v radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 ) -alkoxy and halo-(C 1 -C 4 )-alkoxy.

7. A compound as claimed in claim 1 , wherein

R 1a , R 1b independently are each Cl, Br, NO 2 , CH 3 , CH 3 SO 2 or C 2 H 5 SO 2 ;

R 2 , R 3 are each hydrogen or (C 1 -C 6 )-alkyl; and

R 5 is methyl or ethyl.

8. A herbicidal composition comprising a herbicidally effective amount of at least one compound of the general formula (I) as claimed in claim 1 .

9. A herbicidal composition as claimed in claim 8 in a mixture with formulating auxiliaries.

10. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the general formula (I) as claimed in claim 1 to the plants or to the site of the unwanted plant growth.

11. A compound of the formula (I) or salt thereof

in which the radical and the indices have the following definitions:

X is O,

L is CH 2 ;

Y is oxygen;

R 1a , R 1b , R 1c independently are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato,

(C 1 -C 6 )-alkyl-CO—O, (C 1 -C 6 )-alkyl-S(O) n —O, (C 1 -C 6 )-alkyl-S(O) m , (C 1 -C 6 )-haloalkyl-S(O) m , (C 3 -C 7 )-cycloalkyl-S(O) m , di-(C 1 -C 6 )-alkyl-N—SO 2 , (C 1 -C 6 )-alkyl-SO 2 —NH, (C 1 -C 6 )-alkyl -NH—CO, di-(C 1 -C 6 )-alkyl-N—CO, (C 1 -C 6 )-alkyl-SO 2 —[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-CO—[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-O—CH 2 , (C 1 -C 6 )-alkyl-S(O) n -CH 2 , (C 1 -C 6 )-alkyl-NH—CH 2 , 1,2,4-triazol-1-yl, 1,2,4-triazol-1-yl-CH 2 ,

R 2 , R 3 independently are each hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 9 )-cycloalkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl, the last 5 of the abovementioned radicals being substituted by v radicals selected from the group consisting of cyano, nitro and halogen,

or are each aryl, or (C 1 -C 6 ), the last 2 radicals being substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl-(Y) p and halo-(C 1 -C 6 )-alkyl-(Y) p ,

R 4 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl, (C 3 -C 9 )-cycloalkyl or (C 3 -C 9 )-halocycloalkyl;

R 5 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-halo-cycloalkyl, or is phenyl substituted by v radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 )-alkoxy;

m is 1 or 2;

n is 0, 1 or 2;

p is 0 or 1;

v is 0, 1, 2 or 3;

w and x independently are each 0, 1, 2, 3 or 4;

w and x should not both be zero at the same time.

12. A compound of the formula (I) or salt thereof

in which the radical and the indices have the following definitions:

X is O,

L is CH 2 ;

Y is oxygen;

R 1a , R 1b , R 1c independently are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl-CO—O, (C 1 -C 6 )-alkyl-S(O) n —O, (C 1 -C 6 )-alkyl-S(O) m , (C 1 -C 6 )-haloalkyl-S(O) m , (C 3 -C 7 )-cycloalkyl-S(O) m , di-(C 1 -C 6 )-alkyl-N—SO 2 , (C 1 -C 6 )-alkyl-SO 2 —NH, (C 1 -C 6 )-alkyl-NH—CO, di-(C 1 -C 6 )-alkyl-N—CO, (C 1 -C 6 )-alkyl-SO 2 —[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-CO—[(C 1 -C 6 )-alkyl]amino, (C 1 -C 6 )-alkyl-O—CH 2 , (C 1 -C 6 )-alkyl -S(O) n —CH 2 , (C 1 -C 6 )-alkyl-NH—CH 2 , 1,2,4-triazol-1-yl, 1,2,4-triazol-1-yl-CH 2 ,

or are each (C 1 -C 6 )-alkyl-(Y) p , (C 2 -C 6 )-alkenyl-(Y) p , (C 2 -C 6 )-alkynyl-(Y) p ,

(C 3 -C 9 )-cycloalkyl-(Y) p , (C 3 -C 9 )-cycloalkenyl-(Y) p , (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl-(Y) p or (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkenyl-(Y) p each of which is substituted by v radicals selected from the group consisting of cyano, nitro and halogen, and at least one of R 1a , R 1b , R 1c is 1,2,4-triazol-1-yl or 1,2,4-triazol-1-yl-CH 2 ;

R 2 , R 3 independently are each hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-cycloalkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 9 )-cycloalkenyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 9 )-cycloalkenyl, straight-chain or branched [O—C(R 6 ) 2 ] w —[O—C(R 6 ) 2 ] x —R 6 , (C 1 -C 6 )-alkyl-aryl, (C 2 -C 6 )-alkenyl-aryl, (C 2 -C 6 )-alkynyl-aryl, straight-chain or branched [O—C(R 6 ) 2 ] w —[O—C(R 6 ) 2 ] x -aryl, the last 16 of the abovementioned radicals being substituted by v radicals selected from the group consisting of cyano, nitro and halogen,

or are each aryl, heterocyclyl or heteroaryl each substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl-(Y) p and halo -(C 1 -C 6 )-alkyl-(Y) p ,

R 4 is hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkyl, (C 3 -C 9 )-cycloalkyl or (C 3 -C 9 )-halocycloalkyl;

R 5 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 9 )-cycloalkyl, (C 3 -C 9 )-halo-cycloalkyl, or is phenyl substituted by v selected radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and halo-(C 1 -C 4 ) -alkoxy;

m is 1 or 2;

n is 0, 1 or 2;

p is 0 or 1;

v is 0, 1, 2 or 3;

w and x independently are each 0, 1, 2, 3 or 4;

w and x should not both be zero at the same time.

13. A compound as claimed in claim 11 , wherein

R 1a , R 1b independently are each F, Cl, Br, CH 3 , CH 3 S, CH 3 O, CH 3 SO 2 , C 2 H 5 SO 2 , CF 3 CH 2 SO 2 , cyclopropyl-SO 2 , CF 3 or NO 2 .

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 036801/0914 →