Substituted cyanophenyl uracils

Details Substituted cyanophenyl uracils Substituted cyanophenyl uracils

1997-12-22

2002-12-17

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S230000, C504S235000, C544S219000, C544S295000, C544S310000

Reexamination Certificate

active

06495491

ABSTRACT:

The invention relates to novel substituted cyanophenyluracils, to processes for their preparation and to their use as crop treatment agents, in particular as herbicides and insecticides.
Certain substituted phenyluracils are known to have herbicidal properties (cf. EP-408 382/U.S. Pat. Nos. 5,084,084/5,127,935/5,154,755, EP-563 384, EP-648 749, WO 91/00278, U.S. Pat. Nos. 4,979,982, 5,169,430). However, these compounds have hitherto not attained any major importance.
This invention provides the novel substituted cyanophenyluracils of the general formula (I)
in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, cyano or halogen,
R
2
represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl and heterocyclylalkyl,
R
3
represents hydrogen, halogen or represents a respectively optionally substituted radical from the group consisting of alkyl and alkoxy,
R
4
represents optionally substituted alkyl and
R
5
represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkoxy, alkenyl and alkinyl,
but excluding the known compounds 1-(4-cyano-2-fluoro-5-methylthio-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, 1-(4-cyano-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine and 1-[4-cyano-2-fluoro-5-(1-ethoxycarbonyl-ethylthio)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine (cf EP-408 382, p. 85 and U.S. Pat. No. 5,084,084, Col. 76) by disclaimer.
The novel substituted cyanophenyluracils of the general formula (I) are obtained when
(a) substituted halogenophenyluracils of the general formula (II)
 in which
R
1
, R
3
, R
4
and R
5
are each as defined above and
X represents halogen,
are reacted with nucleophilic compounds of the general formula (III)
M—Q—R
2
  (III)
in which
Q and R
2
are each as defined above and
M represents hydrogen or an alkali metal,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(b) substituted cyanophenyluracils of the general formula (Ia)
 in which
Q, R
1
, R
2
, R
3
and R
4
are each as defined above
are reacted with an alkylating agent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
The novel substituted cyanophenyluracils of the general formula (I) have strong herbicidal and insecticidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably flurorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I)
in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, cyano, fluorine or chlorine,
R
2
represents hydrogen, represents respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl-, C
1
-C
4
-alkoxy-carbonyl-, di-(C
1
-C
4
-alkyl)-amino-carbonyl- or N—C
1
-C
4
-alkyl-N-phenyl-amino-carbonyl- (where the phenyl group is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl or methoxy) substituted alkyl, alkenyl or alkinyl having in each case up to 10 carbon atoms, represents. respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl- or C
1
-C
4
-alkoxy-carbonyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and optionally up to 4 carbon atoms in the alkyl moiety, represents respectively optionally cyano-, carboxyl-, nitro-, carbamoyl-, thiocarbomyl-, fluorine-, chlorine-, bromine-, or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-alkylsulphinyl-, C
1
-C
4
-alkyl-sulphonyl-, C
1
-C
4
-alkyl-carbonyl- or C
1
-C
4
-alkoxy-carbonyl- (each of which is optionally by fluorine and/or chlorine), or phenyl-, phenoxy- or phenylthio- (each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy) substituted aryl or arylalkyl having 6 or 10 carbon atoms in the aryl moiety and optionally up to 4 carbon atoms in the alkyl moiety,
R
2
furthermore represents respectively optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, or C
1
-C
4
-alkyl-, 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- or C
1
-C
4
-alkoxy-carbonyl- (each of which is optionally by fluorine and/or chlorine), or phenyl-, phenoxy- or phenylthio- (each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy) substituted substituted furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, quinolinyl or quinoxalinyl,
R
3
represents hydrogen, fluorine, chlorine, bromine or represents respectively optionally fluorine- and/or chlorine-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,
R
4
represents optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms and
R
5
represents hydrogen or represents respectively optionally fluorine-, chlorine- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkenyl or alkinyl having in each case up to 6 carbon atoms,
but excluding the known compounds 1-(4-cyano-2-fluoro-5-methylthio-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, 1-(4-cyano-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine and 1-[4-cyano-2-fluoro-5-(1-ethoxycarbonyl-ethylthio)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine (cf. EP-408 382, p. 85 and U.S. Pat No. 5,084,084, Col. 76) by disclaimer.
The invention in particular provides compounds of the formula (I)
in which
Q represents O, S, SO or SO
2
,
R
1
represents hydrogen, fluorine or chlorine,
R
2
represents hydrogen, represents respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propinyl, butinyl or pentinyl,
R
2
furthermore represents respectively optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl- or propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
R
2
furthermore represents respectively optionally cyano-, carboxyl-, nitro-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl, benzyl or phenylethyl, or
R
2
furthermore represents respectively optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, or phenyl-, phenoxy- or phenylthio-substit

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