Hydroxamic acid derivatives

Details Hydroxamic acid derivatives Hydroxamic acid derivatives

2002-05-14

2004-11-23

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S319000

Reexamination Certificate

active

06821927

ABSTRACT:

Certain hydroxamic acid derivatives having a similar substitution pattern, and their fungicidal action, are already known (compare, for example, WO 95-20570)). However, in particular at low application rates and concentrations, the activity of these prior-art compounds is not entirely satisfactory in all areas of use.
This invention, accordingly, provides the novel hydroxamic acid derivatives of the general formula (I)
in which
Z represents in each case substituted or unsubstituted cycloalkyl, aryl or heterocyclyl,
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represent hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,
R
1
represents hydrogen or alkyl and
R
2
represents hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl or arylcarbonyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino. Unless stated otherwise, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl, which may optionally also be fuzed to further aliphatic or heterocyclic rings. Thus, aryl also represents tetralinyl, indolyl or benzofuranyl, for example; however, the point of attachment is at the phenyl moiety.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulfur. If the ring contains a plurality of oxygen atoms, these are not adjacent. The cyclic compounds may optionally form a polycyclic ring system with other carbocyclic or heterocyclic fuzed-on or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which may optionally form a polycyclic ring system with other carbocyclic fuzed-on or bridged rings.
A polycyclic ring system may be attached to a heterocyclic ring or a fuzed-on carbocyclic ring. The heterocyclyl radical described in this manner may also be mono- or polysubstituted, preferably by methyl, ethyl, halogen or chlorine. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic ring systems.
Halogenoalkoxy represents partially or fully halogenated alkoxy. In the case of polyhalogenated halogenoalkoxy, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and, in particular, chlorine. If the halogenoalkoxy carries other substituents, the maximum possible number of halogen atoms is reduced to the different free valencies.
Halogenoalkyl represents partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different.
Preferred halogen atoms are fluorine and chlorine, in particular fluorine. If the halogenoalkyl carries other substituents, the maximum possible number of halogen atoms is reduced to the remaining free valencies.
Furthermore, it has been found that the novel hydroxamic acid derivatives of the general formula (I) are obtained when
a) carboxylic acid derivatives of the formula (II)
in which
L
1
, L
2
, L
3
, L
4
and Z are as defined above and
X
1
represents halogen, are reacted with a substituted or unsubstituted hydroxylamine derivative of the general formula (III)
in which
R
1
and R
2
are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, or when
b) compounds of the general formula (I) where R
2
is hydrogen are reacted with a halogen compound of the general formula (IV)
X
2
—R
2
′  (IV)
in which
R
2
′ represents alkyl, alkylcarbonyl, alkoxycarbonyl or arylcarbonyl and
X
2
represents halogen, if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor.
Finally, it has been found that the novel hydroxamic acid derivatives of the general formula (I) have very strong very strong activity against pests of plants.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z. What is claimed are both the E and the Z isomers, and also any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
Z represents cycloalkyl having 3 to 7 carbon atoms which is optionally mono- to disubstituted by halogen, alkyl or hydroxyl;
represents heterocyclyl having 3 to 7 ring members which is optionally substituted by alkyl having 1 to 4 carbon atoms;
or represents phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in the hydrocarbon chains in question;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
in each case doubly attached alkylene having 3 to 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, each of which radicals is optionally mono- to tetrasubstituted by identical or different radicals from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
or a grouping
in which
A
1
represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, phenyl, benzyl or represents in each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4 carbon atoms, and also phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, having in each case 1 to 3 carbon atoms in the alkyl moieties in question, each of which radicals is optionally mono- to trisubstituted in the cyclic moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms,
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms, each of which radicals is optionally substitute

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