1-Amino-3-benzyluracils

Details 1-Amino-3-benzyluracils 1-Amino-3-benzyluracils

1998-03-17

2001-07-31

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C544S311000, C544S312000, C544S002000, C544S053000, C544S054000, C544S055000, C544S065000, C540S544000, C540S601000, C504S219000, C504S221000, C504S223000

Reexamination Certificate

active

06268311

ABSTRACT:

The present invention relates to 1-amino-3-benzyluracils of the formula I
where the variables have the following meanings:
X is oxygen or sulfur;
R
1
is C
1
-C
4
-haloalkyl;
R
2
is hydrogen or halogen;
R
3
and R
7
independently of one another are hydrogen, cyano, thiocyanato, halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy or C
1
-C
4
-haloalkylthio;
R
4
is hydrogen, cyano, thiocyanato, halogen, C
1
-C
4
-alkyl, C
l
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkylthio or C
1
-C
6
-alkylaminocarbonyl;
R
5
is hydrogen, cyano, nitro, halogen, hydroxyl, C
1
-C
4
-alkoxy, amino or C
1
-C
6
-alkylamino; and
R
6
is hydrogen, cyano, nitro, halogen, hydroxyl, C
1
-C
4
-alkoxy, amino, C
1
-C
6
-alkylamino or formyl;
and to the agriculturally useful salts of the compounds I.
The invention furthermore relates to
the use of the compounds I as herbicides and/or for the desiccation and/or defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants, which comprise the compounds I as active ingredients,
processes for the preparation of the compounds I and of herbicidal compositions and compositions for the desiccation and/or defoliation of plants using the compounds I,
methods of controlling undesirable vegetation and for the desiccation and/or defoliation of plants using the compounds I, and
novel intermediates of the formulae III and IV.
3-Benzyl-1-methyl-6-trifluoromethyluracils of the formula II
where
R
a
is hydrogen, cyano, halogen, lower alkoxy, lower alkylaminocarbonyl or propargyloxy and
R
b
is hydrogen, cyano, halogen, lower alkylaminocarbonyl or carboxyl
are described as herbicides in WO 95/04461.
However, the herbicidal action, against the harmful plants, of the known compounds is not always entirely satisfactory.
Accordingly, it was an object of the present invention to provide novel herbicidally active compounds with which targeted control of undesirable plants can be effected better than has been possible to date. Another object is to provide novel compounds which act as desiccants/defoliants.
Accordingly, we have found that this object is achieved by the 1-amino-3-benzyluracils of the formula I defined at the outset. We have furthermore found herbicidal compositions which comprise the compounds I and which have a very good herbicidal action. Moreover, we have found processes for the preparation of thees compositions and methods of controlling undesirable vegetation using the compounds I.
Furthermore, we have found that the compounds I are also suitable for the defoliation and desiccation of parts of plants, suitable plants being crop plants such as cotton, potatoes, oilseed rape, sunflowers, soya beans or faba beans, in particular cotton. Thus, we have found compositions for the desiccation and/or defoliation of plants, processes for the preparation of these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can have one or more chiral centers, in which case they are present as enantiomers or diastereomer mixtures. The invention also relates to the pure enantiomers or diastereomers and also to their mixtures.
Suitable amongst the agriculturally useful salts are, especially, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal action of the compounds I. Thus, suitable cations are, in particular, the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion which, if desired, can have attached to it one to four C
1
-C
4
-alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are, mainly, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
With a view to the use of the compounds of the formula I according to the invention as herbicides and/or as compounds which act as defoliants/desiccants, the variables preferably have the following meanings, in each case on their own or in combination:
X is oxygen;
R
1
is trifluoromethyl;
R
2
is hydrogen;
R
3
is chlorine;
R
4
is hydrogen, cyano, halogen, C
1
-C
4
-alkoxy or C
1
-C
3
-alkylaminocarbonyl; and
R
7
is hydrogen.
The organic moieties mentioned for the substituents R
1
, R
3
, R
4
and R
7
are collective terms for individual enumerations of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, haloalkylthio and alkylaminocarbonyl moieties, can be straight-chain or branched. Unless otherwise indicated, halogenated substituents preferably have attached to them one to five identical or different halogen atoms. The meaning halogen represents in each case fluorine, chlorine, bromine or iodine.
Further meanings are, for example,
C
1
-C
4
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particular methyl or ethyl;
C
1
-C
4
-haloalkyl: a C
1
-C
4
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular trifluoromethyl or 1,2-dichloroethyl;
C
1
-C
4
-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular methoxy, ethoxy, 1-methylethoxy or 1,1-dimethylethoxy;
C
1
-C
4
-haloalkoxy: C
1
-C
4
-alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine and/or bromine, e.g. chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably difluoromethoxy, trifluoromethoxy or pentafluoroethoxy;
C
1
-C
4
-alkylthio: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio, in particular methylthio or ethylthio;
C
1
-C
4
-haloalkylthio: C
1
-C
4
-alkylthio as mentioned

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