Fungicide salts

Details Fungicide salts Fungicide salts

1998-10-27

2000-02-29

Raymond, Richard L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514161, 544330, C07D23948, A01N 4104, A01N 4354, A01N 3710, A01N 3702

Patent

active

060309776

DESCRIPTION:

BRIEF SUMMARY
This invention relates to compounds having fungicidal activity.
Pyrimethanil is a known fungicide, having the chemical name, 2-anilino-4,6-dimethylpyrimidine. However it has a relatively high vapour pressure which restricts it use. We have found that combining pyrimethanil with certain acids confers certain advantages to the compound.
According to the invention there is provided a product obtained by combining pyrimethanil with an organic acid, selected from long chain fatty acids, such as oleic acid and palmitic acid, saccharin, sulfonic acids, such as camphorsulfonic acid, salicylic acid and jasmonic acid.
It is generally preferred that the acid is present in at least a stoichiometric amount and in this case a salt is usually formed between pyrimethanil and the acid. Excess acid may be an advantage, e.g. in a molar ratio of acid to pyrimethanil of up to 2:1.
Certain salts of pyrimethanil are novel and useful and the invention also includes salts of pyrimethanil with an organic acid having a volatility of less than 2 Pa at 20.degree. C.
As stated above one advantage of the products of the invention in particular is that they have a reduced vapour pressure compared with the free pyrimethanil, which increases the persistence of the compound on the crop to be protected from fungal attack. The reduced volatility also reduces levels of fungicide in the atmosphere.
In many cases the products have reduced phytotoxicity to certain plants.
In some cases the salts have increased activity compared with the free pyrimethanil. Another advantage is that the products have physical and chemical properties, which often make them amenable to provide better formulations than the free pyrimethanil. For example, the product of pyrimethanil with oleic acid is liquid which provides formulation advantages compared with the free pyrimethanil, which is a solid.
The products are useful in combating diseases for which pyrimethanil may be used e.g. Botrytis spp., especially B. cinerea, Venturia spp, Altenaria spp., and Monolinia fructigena. However the salt may also extend the useful activity to diseases such as mildews and particularly cereal powdery mildew (Erysiphe graminis) and glume blotch (Leptosphaeria nodorum).
The invention is illustrated in the following Examples.


EXAMPLE 1

A solution of pyrimethanil (1.0 g), toluene (50 ml) and oleic acid (1.42 g) was allowed to stand overnight at room temperature. The toluene was evaporated under reduced pressure to give pyrimethanil oleate, as an oil. (compound 1) nmr data:


______________________________________ CDCI3 & scale ______________________________________ 0.9 (3H, t, CH3) 1.25 -1.42 (20H, m, 10 .times. CH2) 1.62 -1.76 (2H, m, CH2) 1.95 -2.1 (4H, m, 2 .times. CH2) 2.34 -2.42 (8H, m, 2 .times. CH3, CH2) 5.3 -5.42 (2H, m, CH.dbd.CH) 6.47 (1H, s, pyrimidine CH) 7.0 (1H, t, ArH) 7.32 (2H, t, ArH) 7.72 (2H, d, ArH) 8.67 (1H, brs, NH) ______________________________________


EXAMPLE 2

A solution of camphorsulfonic acid (1.25 g) in ethanol (10 ml) was added slowly to a solution of pyrimethanil (1 g) in toluene (20 ml) and the mixture allowed to stand for 30 minutes at room temperature. The mixture was evaporated under reduced pressure and the residue recrystallised from a mixture of diisopropyl ether and ethyl acetate to give pyrimethanil camphorsulfonate, m.p. 1 66-7.degree. C. (compound 2)
In a similar way there was obtained (compound 4) 5) (compound 6) (compound 8)


EXAMPLE 3

This Example illustrates relative persistence of the products of the invention compared with the free anilinopyrimidine.
Droplets (5.times.4 .mu.l) of toluene solutions of radiolabelled pyrimethanil (0.05% w/v) were applied to microscope cover slips (13 mm diameter), which were positioned in Petri dishes. To some of the samples were added various fatty acids in molar ratios of pyrimethanil to acid of 1:1 and 1:2. The Petri dishes were left in a controlled environment room (20.degree. C., 16 hours daylight) and after two days, slips were removed to determine how m

REFERENCES:
P. Leroux, "Influence du pH, d'acides amines et de diverss substances organiques sur la fongitoxicite du pyrimethanil ( . . . ) vis-a-vis de certaines souches de Botrytis cinerea", Agronomie, vol. 14, 1994, pp. 541-554.

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