Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-05-03
2003-09-23
Rao, Deepak (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S310000
Reexamination Certificate
active
06624119
ABSTRACT:
The present invention relates to 3-[benz(ox/othi)azol-7-yl]-1H-pyrimidine-2,4-diones of the formula I
in which:
X is oxygen or sulfur;
Y is oxygen or sulfur;
Z is a chemical bond, C
1
-C
4
-alkylene, oxygen, sulfur, SO or SO
2
;
R
1
is hydrogen, amino, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
2
is hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl or C
1
-C
6
-alkylsulfonyl;
R
3
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
4
is hydrogen or halogen;
R
5
is cyano, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
6
is hydrogen, C
3
-C
7
-cycloalkyl or 3- to 7-membered saturated heterocyclyl containing one or more oxygen and/or sulfur atoms, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member, and where each cycloalkyl and heterocyclyl ring may be unsubstituted or may carry from one to four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-cyanoalkyl, C
1
-C
4
-hydroxyalkyl, C
1
-C
4
-aminoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, (C
1
-C
4
-alkoxy)carbonyl, (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, (C
1
-C
4
-alkyl)carbonyloxy, (C
1
-C
4
-haloalkyl)carbonyloxy, di(C
1
-C
4
-alkyl)amino, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
4
-alkenyloxy, C
3
-C
4
-alkenylthio, C
3
-C
4
-alkynyloxy and C
3
-C
4
-alkynylthio,
with the proviso that R
6
is hydrogen only if Y is oxygen and Z is a chemical bond and that R
6
is not C
3
-C
6
-cycloalkyl if Y is sulfur,
and the agriculturally useful salts of the compounds I.
Moreover, the invention relates to
the use of the compounds I as herbicides,
herbicidal compositions comprising the compounds I as active substances,
processes for preparing the compounds I and herbicidal compositions using the compounds I,
methods for controlling undesirable vegetation using the compounds I, and
intermediates of the formulae III, IV, V and VI for preparing the compounds I.
WO 97/08170 describes certain 3-(benz(ox/othi)azol-7-yl)-6-(trifluoromethyl)uracils for use as herbicides. Other 3-(benzothiazol-7-yl)uracils and their use as herbicides and for the desiccation/defoliation of plants are described in WO 97/08171. WO 97/12886 provides, inter alia, certain 3-benzisoxazol-7-yl-2,4-(1H,3H)pyrimidinediones which are said to have herbicidal and desiccant action.
It is an object of the present invention to provide novel herbicidally active uracil compounds which allow better targeted control of undesirable plants than the known uracil compounds.
We have found that this object is achieved by the present 3-[benz(ox/othi)azol-7-yl]-1H-pyrimidine-2,4-diones of the formula I.
We have furthermore found herbicidal compositions comprising the compounds I and having very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
Suitable agriculturally useful salts are in particular the salts of those cations or the acid addition salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I. Thus, suitable cations are, in particular, 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 also the ammonium ion which, if desired, may carry from one to four C
1
-C
4
-alkyl substituents and/or one 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 usable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrage, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic moieties mentioned in the definition of the substituents R
1
, R
2
, R
3
, R
5
and R
6
or as radicals on saturated cycloalkyl or saturated heterocyclic rings are—like the term halogen—collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy and alkynylthio moieties can be straight-chain or branched. Halogenated substituents preferably carry from one to five identical or different halogen atoms. The meaning of halogen is in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C
1
-C
4
-alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl;
C
1
-C
4
-alkylene: methylene, 1,2-ethylene, 1,1-ethylene, 1,3-propylene, 1,2-propylene, 2,2-propylene, 1,4-butylene or 2,3-butylene;
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, i.e., for example, CH
2
F, CHF
2
, CF
3
, CH
2
C1, CH(Cl)
2
, C(Cl)
3
, 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, C
2
F
5
, 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, CH
2
—C
2
F
5
, CF
2
—C
2
F
5
, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
C
1
-C
6
-alkyl: a C
1
-C
4
-alkyl radical as mentioned above or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably CH
3
, C
2
H
5
, CH
2
—C
2
H
5
, CH(CH
3
)
2
, n-butyl, C(CH
3
)
3
, n-pentyl or n-hexyl;
C
1
-C
6
-haloalkyl: a C
1
-C
6
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C
1
-C
4
-haloalkyl or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl;
cyano-C
1
-C
4
-alkyl: CH
2
CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1-(CH
2
CN)eth-1-
Hamprecht Gerhard
Menke Olaf
Otten Martina
Reinhard Robert
Schäfer Peter
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