Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-03
2002-05-07
Ford, John M. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S278000
Reexamination Certificate
active
06384040
ABSTRACT:
This application is a US National Phase Application filed under 35 USC 371 of PCT/EP99/00686 filed Feb. 2, 1999.
The present invention relates to compounds of formula I, which have microbicidal activity, in particular fungicidal activity. The invention also relates to the preparation of these substances, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ing redients or compositions inite a Mric eulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
The 4-thioxopyrimidines according to the invention have the general formula I
wherein R
1
is chlorine or bromine and R
3
and R
4
are independently propyl or butyl.
4-Pyrimidinones with fungicidal properties useful in agricultural practice are known from U.S. Pat. No. 3,755,582, WO 94/26722, WO 97/02262 and WO 97/33890. The disclosed compounds for practical purposes do not always satisfy the needs of the modern agriculture.
Surprisingly, it has now been found that the thieno[2,3-d]pyrimidine derivatives of formula I exhibit improved biological properties which render them more suitable for the practical use in agriculture and horticulture.
The compounds of formula I may be obtained in the form of their acid addition salts. Such acid addition salts are, for example, formed with mineral acids, typically sulfuric acid, a phosphoric acid or a hydrogen halide, with organic carboxylic acids, typically acetic acid, oxalic acid, malonic acid, maleic acid, fumaric acid or phthalic acid, with hydroxycarboxylic acids, typically ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or with benzoic acid, or with organic sulfonic acids, typically methanesulfonic acid or p-toluenesulfonic acid.
Within the present specification propyl and butyl denote n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl. Non-branched alkyl is preferred.
Preferred individual compounds are:
6-chloro-2-propoxy-3-propyl-4-thioxo-thieno[2,3-d]pyrimidine,
3-butyl-6-chloro-2-propoxy-4-thioxo-thieno[2,3-d]pyrimidine,
6-bromo-2-propoxy-3-propyl-4-thioxo-thieno[2,3-d]pyrimidine, and
6-bromo-3-butyl-2-propoxy-4-thioxo-thieno[2,3-d]pyrimidine.
The compounds of formula I may be obtained by treatment of a compound of formula II
wherein R
1
, R
3
and R
4
are as defined for formula I, with a sulfurating agent, e.g. P
2
S
5
or the Lawesson reagent. The reaction conditions for sulfurating reactions of this type are well known in the art (B. A. Jones, J. S. Bradstaw, Chem. Rev. 1984 (84), 17-30) and for the purpose of present invention is conveniently carried out in analogy to known procedures. Advantageously, the reaction is carried out in an inert solvent, e.g. dioxane, tetrahydrofurane, toluene, xylene and the like, and at a temperature in the range of the boiling point of the reaction mixture, conveniently at reflux. The starting material of formula II is known from the prior documents cited above.
Alternatively, the compounds of formula I may be obtained by alcoholysis of a compound of formula III
wherein R
1
, R
3
and R
4
are as defined for formula I, in the presence of a base with an alcohol of formula IV
HO—R
4
(IV)
Suitably the base is selected from the alkali salts of the employed alcohol, and the reaction is carried out in an excess of the alcohol which may at the same time serve as solvent. In a variant the alcohol may be employed only in slight excess, and an inert solvent may be employed.
The starting material of formula III has especially been developed for the present invention. It is therefore another part of this invention.
The compounds of formulae I and III may be obtained according to the following schemes:
Surprisingly, it has now been found that the novel compounds of formula I have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.
The compounds of formula I can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic micro-organisms.
It is also possible to use compounds of formula I as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
The compounds I are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp,
Erwinia amylovora
as well as against the tobacco mosaic virus).
Within the scope of present invention, target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and relate species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflower, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit mandarins); vegetables (spinache, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.
The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilisers, antifoams, viscosity regulators, binders or tackifiers as well as fertilisers, micronutrient donors or other formulations for obtaining special effects.
Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilisers. Such carriers are for example described in WO 97/33890.
The compounds of formula I are normally used in the form of
Ford John M.
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
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