Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-10-31
1998-01-13
Powers, Fiona T.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504282, 514341, 514403, 514407, 544405, 5462761, 5483661, 5483664, 5483694, 5483711, A01N 4356, C07D23108, C07D23120, C07D40104, C07D40304
Patent
active
057079366
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/01554 filed Apr. 25, 1995.
The present invention relates to methyl .alpha.-phenylbutenoates of the formula I ##STR2## where ---- is a single or double bond and the index and the substituents have the following meanings:
n is 0, 1, 2, 3 or 4, it being possible for the substituents R.sup.1 to be different if n is greater than 1;
R.sup.1 is nitro, cyano, halogen, C.sub.1-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkoxy;
R.sup.2 is hydrogen, nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -alkoxycarbonyl;
R.sup.3 is unsubst. or subst. alkyl, alkenyl or alkynyl; addition to carbon atoms, can contain one to three of the following heteroatoms as ring members: oxygen, sulfur and nitrogen, or to carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or sulfur atom as ring members.
The invention additionally relates to processes for preparing these compounds, mixtures containing them and their use for controlling harmful fungi or animal pests.
EP-A 513 580 discloses methyl .alpha.-phenylbutenoates with action against harmful fungi or animal pests, which carry a 4-pyrazolyl-oxymethylene radical in the ortho position. The action of these compounds is unsatisfactory, however, at low application rates.
It is an object of the present invention to provide compounds having improved actions.
We have found that this is achieved by the compounds I defined at the outset. In addition, we have found processes for their preparation, mixtures containing them and methods for controlling harmful fungi and animal pests using the compounds I.
The compounds I can be obtained by various methods known per se from the literature.
For example, the compounds I are obtained by reaction of the benzyl derivative of the formula II with a 3-hydroxy(dihydro)-pyrazole of the formula III in the presence of a base. ##STR3##
L in the formula II is a nucleophilically replaceable group, for example halogen, eg. chlorine, bromine or iodine, or an alkyl- or arylsulfonate, eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or 4-methylphenylsulfonate.
The reaction is customarily carried out at from 0.degree. C. to 80.degree. C., preferably from 20.degree. C. to 60.degree. C.
Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyi ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, and also dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride, acetone and dimethylformamide. Mixtures of the solvents mentioned can also be used.
Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides (eg. lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal and alkaline earth metal oxides (eg. lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal and alkaline earth metal hydrides (eg. lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (eg. lithium amide, sodium amide and potassium amide), alkali metal and alkaline earth metal carbonates (eg. lithium carbonate and calcium carbonate) and also alkali metal hydrogen carbonates (eg. sodium hydrogen carbonate), organometallic compounds, in particular alkali metal alkyls (eg. such as methyllithium, butyllithium and phenyllithium), alkylmagnesium halides (eg. methylmagnesiumchloride) and also alkali metal and alkaline earth metal alkoxides (eg. sodium methoxide, sodium ethoxide, pota
REFERENCES:
patent: 4937372 (1990-06-01), Wenderoth et al.
patent: 5192357 (1993-03-01), Cliff et al.
patent: 5298527 (1994-03-01), Grammenos et al.
Ammermann Eberhard
Grammenos Wassilios
Harries Volker
Kirstgen Reinhard
Konig Hartmann
BASF - Aktiengesellschaft
Powers Fiona T.
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