Substituted aryluracils

Details Substituted aryluracils Substituted aryluracils

1999-10-07

2002-09-10

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S311000, C544S312000, C544S313000, C544S314000, C544S310000, C544S284000, C544S295000, C544S296000, C504S240000, C504S235000, C504S236000, C504S237000, C504S238000

Reexamination Certificate

active

06448203

ABSTRACT:

This is a 371 of PCT EP 98/01847 filed Mar. 30, 1998.
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted aryluracils, to processes for their preparation and to their use as crop protection agents, in particular as herbicides and insecticides.
BACKGROUND OF THE INVENTION
A large number of substituted aryluracils are already known from the (patent) literature (cf. JP 05202031, JP 05039272, U.S. Pat. No. 5344812, U.S. Pat. No. 5399543, WO 9511096). However, these compounds have hitherto not attained any particular importance.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel substituted aryluracils of the general formula (I)
in which
n represents the numbers 0, 1, 2 or 3,
Q represents O, S, SO or SO
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,
R
3
represents hydrogen, halogen or optionally substituted alkyl.
Y represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino, and
z represents optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, irnidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, or represents in each case substituted thiazolyl, isothiazolyl, benzothiazolyl or benzimidazolyl.
The novel substituted aryluracils of the general formula (I) are obtained when
(a) aminoalkenoic esters of the general formula (II)
 in which
R
2
and R
3
are each as defined above and
A
1
represents alkyl, aryl or arylalkyl
are reacted with arylurethanes (arylcarbamates) of the general formula (III)
 in which
n, Q, Y and Z are each as defined above and
A
2
represents alkyl, aryl or arylalkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) substituted aryluracils of the general formula (IV)
 in which
n, Q, R
1
, R
2
, R
3
and Y are each as defined above
are reacted with halogenomethylheterocycles of the general formula (V)
XCH
2
—Z  (V)
 in which
Z is as defined above and
X represents halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) substituted aryluracils of the general formula (Ia)
 in which
n, Q, R
2
, R
3
, Y and Z are each as defined above
are reacted with 1-arninooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VI)
X
1
—A
3
  (VI)
 in which
A
3
represents optionally substituted alkyl and
X
1
represents halogen or the grouping —O—SO
2
—O—A
3
.
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
The novel substituted aryluracils of the general formula (I) have strong herbicidal and insecticidal activity.
The invention preferably provices compounds of the formula (I) in which
n represents the numbers 0, 1, 2 or 3,
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, amino or optionally cyano-, halogen-, or C
1
-C
4
-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R
2
represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms,
R
3
represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,
Y represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, halogen, or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino having in each case 1 to 4 carbon atoms in the alkyl groups, and
Z represents optionally substituted heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, dioxanyl, benzodioxanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, or represents in each case substituted thiazolyl, isothiazolyl, benzothiazolyl or benzimidazolyl, where the possible substituents are preferably selected from the list below:
nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, halogen, in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino having in each case 1 to 4 carbon atoms in the alkyl groups or phenyl.
The invention relates in particular to compounds of the formula (I) in which
n represents the numbers 0, 1 or 2,
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, amino or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl or ethyl,
R
2
represents in each case optionally fluorine- and/or chlorine-substituted methyl or ethyl,
R
3
represents hydrogen, fluorine, chlorine, bromine or methyl,
Y represents nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-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, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, acetylamino, propionylarnino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, and
Z represents optionally substituted heterocyclyl from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, dioxolanyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, or represents in each case substituted thiazolyl, benzothiazolyl or benzimidazolyl, where the possible substituents are preferably selected from the list below:
nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, aminosulphonyl, fluorine, chlorine, bromine, in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-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, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino, phenyl.
Very particular

Affiliated with

Also associated with

Rating

Substituted aryluracils 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 aryluracils, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted aryluracils will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2848721