Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-09-09
2000-11-28
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504242, 544298, 544299, A01N 4354, C07D23902
Patent
active
061535605
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The present invention relates to pyrimidyl phenyl and pyrimidyl benzyl ethers of the general formula I ##STR2## and to their salts and N-oxides where the substituents and indices have the following meanings: CH.sub.3).dbd.CHOCH.sub.3, C(CONHCH.sub.3).dbd.CHOCH.sub.3, C(CONH.sub.2).dbd.NOCH.sub.3, C(CONHCH.sub.3).dbd.NOCH.sub.3 or N(OCH.sub.3) --CO.sub.2 CH.sub.3 ; carbon, oxygen, sulfur or nitrogen atom; -haloalkyl; a carbon, oxygen, sulfur or nitrogen atom; different if y is 2 or 3; -haloalkyl or C.sub.1 -C.sub.4 -alkoxy.
The invention furthermore relates to processes and intermediates for the preparation of these compounds and to their use for controlling animal pests and harmful fungi.
Pyrimidylphenyl and -benzyl ethers having fungicidal, or fungicidal and insecticidal, properties have been disclosed in the literature (EP-A 254 426; EP-A 278 595; EP-A 299 694; EP-A 363 818; EP-A 350 691; EP-A 398 692; EP-A 407 873; EP-A 477 631; EP-A 513 580; JP-A 04/182,461; WO-A 93/15,046), which differ from the compounds according to the invention by the substituents in the pyrimidyl moiety.
It was an object of the present invention to provide compounds with an improved activity and a widened spectrum of action.
We have found that this object is achieved by the compounds I defined at the outset. We have furthermore found processes and intermediates for the preparation of these compounds and their use for controlling animal pests and harmful fungi.
The compounds I are accessible via various routes by processes described per se in the literature.
The construction of the group Q is disclosed, for example, in the literature cited at the outset and is carried out in general and in particular by the processes described therein.
Usually, a procedure is followed for the synthesis of the compounds I in which a pyrimidine derivative of the formula IIa is converted with a phenol or a benzyl alcohol of the formula IIIa in an inert solvent to give the corresponding ether of the formula IVa, and IVa is subsequently reacted with an O-substituted hydroxylamine (R.sup.1 --O--NH.sub.2) or a salt thereof to give I. ##STR3##
L.sup.1 in formula IIa is a nucleophilically exchangeable leaving group, such as halogen (eg. fluorine, chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate).
1a) The reaction of IIa with IIIa is normally carried out in an inert solvent at from 0.degree. C. to 130.degree. C., preferably 20.degree. C. to 80.degree. C. in the presence of a base. cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, 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, and also dimethyl sulfoxide and dimethylformamide, especially preferably tetrahydrofuran, acetonitrile, dimethyl sulfoxide and acetone. Mixtures of these can also be used. 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 magnesium oxide, alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal carbonates and alkaline earth metal carbonates, such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and alkali metal alcoholates and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-b
REFERENCES:
patent: 5438059 (1995-08-01), Clough et al.
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harreus Albrecht
BASF - Aktiengesellschaft
Patel Sudhaker B.
Shah Mukund J.
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