Substituted phenyluracils and their use as herbicides

Details Substituted phenyluracils and their use as herbicides Substituted phenyluracils and their use as herbicides

2002-05-07

2004-11-09

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S312000

Reexamination Certificate

active

06815398

ABSTRACT:

The invention relates to novel substituted phenyluracils and novel intermediates for their preparation and to their use as herbicides.
Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255047, EP-A-260621, EP-A-408382, EP-A-438209, EP-A-473551, EP-A-517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, WO-A-98/41093, U.S. Pat. No. 4,979,982, U.S. Pat. No. 5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat. No. 5,169,430, U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863). However, these compounds have hitherto not attained any particular importance.
This invention, accordingly, provides novel substituted phenyluracils of the general formula (I)
in which
n represents the numbers 0, 1 or 2,
R
1
represents hydrogen, amino or optionally substituted alkyl,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
X represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl—where in the case that n is greater than 1, X in the individual possible compounds may also have meanings other than those given.
In the definitions, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy.
If the compounds of the general formula (I) according to the invention contain substituents with asymmetric carbon atoms, the invention relates in each case to the R enantiomers and the S enantiomers, and to any mixtures of these enantiomers, in particular the racemates.
n preferably represents the numbers 1 or 2.
R
1
preferably represents hydrogen, amino or optionally cyano-, carboxyl-, fluorine-, chlorine-, C
1
-C
4
-alkoxy- or C
1
-C
4
-alkoxy-carbonyl-substituted C
1
-C
4
-alkyl.
R
2
preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally fluorine-substituted C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-carbonyl.
X preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, represents in each case optionally hydroxyl-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkylsulphonyl-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, C
2
-C
4
-alkenyl-oxycarbonyl-, C
2
-C
4
-alkinyl-oxycarbonyl-, C
1
-C
4
-alkylamino-carbonyl-, di-(C
1
-C
4
-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxy-carbonyl-, phenylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents dialkylaminocarbonyl or dialkylaminocarbonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents phenylcarbonyloxy, represents in each case optionally fluorine-, chlorine- or bromine-substituted alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine- or C
1
-C
4
-alkoxy-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl having in each case up to 6 carbon atoms.
n particularly preferably represents the number 1.
R
1
particularly preferably represents hydrogen, amino or methyl.
R
2
particularly preferably represents carboxyl, cyano, carbamoyl, methoxycarbonyl or trifluoromethyl.
X particularly preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents dimethylamino or diethylamino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, represents dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, represents n- or i-butylcarbonyloxy, represents phenylcarbonyloxy, represents in each case optionally fluorine- or chlorine-substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, methoxycarbonyl- or ethoxycarbonyl-substituted ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethinyl, propinyl, propinyloxy or propinyloxycarbonyl.
X very particularly preferably represents hydroxyl, mercapto, amino, represents in each case cyano-, carboxyl-, carbamoyl-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yloxycarbonyl-, propargyloxycarbonyl-, 1-butin-3-yloxycarbonyl-, 2-butin-4-yloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, methoxy, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, represents in each case cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl-, 1-buten-3-yloxycarbonyl-, 2-buten-4-yl-oxycarbonyl-, propargyloxycarbonyl-, 1-bu

Affiliated with

Also associated with

Rating

Substituted phenyluracils and their use as herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Substituted phenyluracils and their use as herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted phenyluracils and their use as herbicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3324567