Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-05-28
2000-09-05
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514272, 544295, 544296, 544298, 544316, 544330, A01N 4354, C07D23926, C07D23930, C07D23934
Patent
active
061143421
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to 2-(O-[pyrimidin-4-yl]methyleneoxy)phenylacetic acid derivatives of the general formula I ##STR1## and the salts and N-oxides thereof where the radicals R.sup.1 to R.sup.4 and Q have the following meanings:
R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.2 is halogen, C.sub.1 -C.sub.2 -alkyl or C.sub.1 -C.sub.2 -haloalkyl;
R.sup.3 is hydrogen; amino; hydroxyl; mercapto; halogen; C.sub.1 -C.sub.8 -alkyl, it being possible for the alkyl radicals to have attached to them a phenyl group which, in turn, can have attached to it one or, independently of one another, two of the following substituents: halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl and C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.8 -haloalkyl; C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.8 -alkoxy; C.sub.1 -C.sub.8 -monoalkylamino; di-C.sub.1 -C.sub.8 -alkylamino; C.sub.1 -C.sub.8 -alkylthio; C.sub.1 -C.sub.8 -alkylsulfoxyl; C.sub.1 -C.sub.8 -alkylsulfonyl; C.sub.3 -C.sub.8 -cycloalkyl; tri-C.sub.1 -C.sub.8 -alkylsilyloxy or the following, unsubstituted or substituted in the aromatic ring: phenyl, phenoxy, phenoxymethyl, benzyloxy or heteroaryl;
R.sup.4 is hydrogen; cyano; halogen; C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkoxy;
Q is C(=NOCH.sub.3)--CONHCH.sub.3,
C(=NOCH.sub.3)--COOCH.sub.3 or
N(OCH.sub.3 )--COOCH.sub.3.
In addition, the invention relates to compositions comprising the compounds I and to their use for controlling harmful fungi and animal pests.
Fungicidally and/or insecticidally and acaricidally active methyl .alpha.-[2-(heteroary-loxymethylene)phenyl]-.alpha.-methoxyiminoacetamides have been disclosed (EP-A 398 629; EP-A 477 631; JP-A 04/182 461; German Patent Application File Ref. No. 1 95 26 661.7).
Furthermore, fungicidally and/or insecticidally and acaricidally active methyl .alpha.-[2-(heteroaryloxy-methylene)phenyl]-.alpha.-methoxyiminoacetates have been disclosed (cf. EP-A 254 426, EP-A 363 818, EP-A 407 873).
In addition, fungicidally and/or insecticidally and acaricidally active methyl N-[2-(heteroaryloxymethylene)phenyl]-N-methoxycarbamates have been disclosed (cf. WO-A 93/15046).
The activity of the compounds described in the abovementioned publications is as yet unsatisfactory.
It is an object of the invention to provide novel compounds which have improved properties in the control of harmful fungi and animal pests.
We have found that this object is achieved by the compounds I defined at the outset, by compositions comprising them and by their use for controlling harmful fungi and animal pests.
The compounds I are prepared by methods similar to those described in the literature mentioned at the outset.
When synthesizing the compounds I, it is generally irrelevant whether the group Q or the 2-(0-[pyrimidin-4-yl]-methyleneoxy) group is synthesized first.
For example, the compounds I are obtained by reacting a pyrimidin-4-ol of the formula II with a benzyl derivative of the formula III in a manner known per se in an inert organic solvent in the presence of a base. ##STR2## (Q =C(=NOCH.sub.3)--CONHCH.sub.3), C(=NOCH.sub.3)--COOCH.sub.3 or N(OCH.sub.3)--COOCH.sub.3)
In formula III, X is a nucleophilically exchangeable leaving group such as halogen (eg. chlorine, bromine or iodine), alkylsulfonyl (eg. methylsulfonyl or trifluoromethylsulfonyl) or arylsulfonyl (eg. [phenylsulfonyl or 4-methylphenylsulfonyl).
The reaction is normally carried out at from 0 to 80, preferably from 20 to 60.degree. C.
Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, and also dimethyl sulfoxide, dimethyl formamide, dimethylaceta
REFERENCES:
patent: 5157037 (1992-10-01), Schuetz et al.
patent: 5298527 (1994-03-01), Grammenos et al.
patent: 5334577 (1994-08-01), Wenderoth et al.
patent: 5371222 (1994-12-01), Hayase et al.
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harries Volker
BASF - Aktiengesellschaft
Shah Mukund J.
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