Pyridylcarbamates, process and intermediates for their preparati

Details Pyridylcarbamates, process and intermediates for their preparati Pyridylcarbamates, process and intermediates for their preparati

1998-06-08

1999-11-02

Davis, Zinna Northington

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546304, C07D21376, A01N 4718

Patent

active

059771461

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to pyridylcarbamates of the formula I ##STR2## where the index and the substituents have the following meanings: R' is hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkylcarbonyl and alkoxycarbonyl; cycloalkenyl, or in the event that V is an amino group, additionally hydrogen; attached to it one of the following radicals: alkyl, alkenyl, alkynyl or cycloalkyl; alkynyl, alkoxy, alkenyloxy, alkynyloxy, or in the event that n>1, an unsubstituted or substituted bridge which is bonded to two adjacent C atoms of the pyridyl ring and which contains 3 to 4 members from amongst the group consisting of 3 or 4 carbon atoms, 2 to 3 carbon atoms and one or two nitrogen, oxygen and/or sulfur atoms, it being possible for this bridge together with the ring to which it is bonded to form a partially unsaturated or aromatic radical; an organic radical which is bonded directly or via an oxy, mercapto, amino, carboxyl or carbonylamino group, or together with a group X and the pyridyl ring to which they are bonded an unsubstituted or substituted bicyclic, partially or fully unsaturated system which, in addition to carbon ring members, can contain hetero atoms from amongst the group consisting of oxygen, sulfur and nitrogen,
The literature discloses phenylcarbamates for controlling harmful fungi and animal pests [WO-A 95/15,046].
It is an object of the present invention to provide novel compounds with an improved activity.
We have found that this object is achieved by the compounds I defined at the outset.
We have furthermore found processes and intermediates for their preparation, and their use for controlling animal pests or harmful fungi.
The compounds I are accessible by various routes following processes described in the literature.
When synthesizing the compounds I it is, in principle, irrelevant whether the group R or the carbamate group --N(OR')--COVR" is synthesized first.
The synthesis of the carbamate group --N(OR')--COVR" is disclosed, for example, in the literature cited at the outset. In general, a procedure is followed for this in which the conditions described in items 1.1 to 1.3 are met. reducing a nitropyridine of the formula II to the corresponding hydroxylamine III and subsequently reacting III with an acylating agent of the formula IV to give Ia. ##STR3## L.sup.1 is a nucleophilically exchangeable leaving group, such as halogen (eg. chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate). from -30.degree. C. to 80.degree. C., preferably 0.degree. C. to 60.degree. C., in an inert organic solvent in the presence of a catalyst [cf. Ann. Chem. 316, 278 (1901); EP-A 085 890; DE Application No. 19 50 27 00.01]. from -20.degree. C. to 60.degree. C., preferably 0.degree. C. to 30.degree. C., in an inert organic solvent in the presence of a base [cf. WO-A 93/15, 046].
Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide and dimethyl-formamide, especially preferably cyclohexane, toluene, methylene chloride, tert-butyl methyl ether and water. Mixtures of these can also be used.
Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesiu

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