Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
2001-04-27
2003-02-25
Richter, Johann (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
C514S525000, C558S418000, C558S419000, C558S423000
Reexamination Certificate
active
06525092
ABSTRACT:
The invention relates to novel pesticidally, in particular fungicidally, active bis-oxime compounds of formula I
wherein
a) X is CH, and Y is OCH
3
, or
b) X is N, and Y is OCH
3
, OC
2
H
5
or NHCH
3
;
R
1
is ethyl or cyclopropyl;
R
2
is hydrogen, methyl or ethyl;
R
3
is cyano;
n is 1 or 2.
The formula I embraces all stereoisomeric forms and mixtures thereof, such as racemic and diasteromeric mixtures, for example E/Z mixtures.
1,2-Dioxime ether derivatives having fungicidal activities are known, e.g. from WO 95/18789. It has been found that the compounds according to the invention exhibit improved biological properties which render them very suitable for practical use in agriculture and horticulture by having an extraordinarily good fungicidal activity, especially in cereals.
The invention furthermore relates to the preparation of these compounds, to agrochemical compositions which comprise, as active ingredients, at least one of these compounds, and to the use of the active ingredients or of the compositions for protecting plants against attack by harmful microorganisms, in particular fungi, as well as to intermediates and their preparation.
Preferred groups are
(a) compounds wherein in formula I
R
2
is methyl or ethyl;
R
3
is cyano.
(b) compounds wherein in formula I
X is N, and Y is OCH
3
, or NHCH
3
;
R
2
is methyl;
R
3
is 4-cyano.
Also preferred are the compounds of the Tables, in particular compound No. 1.3
The compounds of formula I can be prepared as follows:
A) To obtain a compound of formula I wherein X, Y, R
1
, R
3
and n are as defined for formula I and R
2
is methyl or ethyl:
A compound of formula II, wherein the substituents are as defined for formula I and U is a leaving group, for example chlorine, bromine, iodine, mesyloxy or tosyloxy, is reacted with a compound of formula III, wherein the substituents are as defined above, preferably in an organic solvent in presence of a base.
B) To obtain a compound of formula I, wherein X, Y, R
1
, R
3
and n are as defined for formula I and R
2
is hydrogen (formula I.b):
In an analogous reaction as described under A), compounds of formula II and IV, wherein the substituents are as defined under A) above, are reacted to give a compound of formula V which is further reacted with H
2
NOH to give a compound of formula I.b.
C) To obtain a compound of formula I, wherein X is N and Y is NHCH
3
: A compound of formula I, wherein X is N and Y is OCH
3
or OC
2
H
5
is reacted in a solvent with NH
2
CH
3
.
Compounds of formula II are known, e.g. from WO95/18789.
Compounds of formulae III, wherein R
1
, R
2
, R
3
and n are as defined for formula I are part of the present invention and can be prepared as follows:
(a) Reacting a compound of formula VII, wherein the substituents are as defined for formula I, with nitrous acid or with an organic nitrite, e.g. a C
1
-C
6
alkyl nitrite such as pentyl nitrite, to give a compound of formula IV, which is converted to a compound of formula III
(b1) either directly with O-methylhydroxylamine or with O-ethylhydroxylamine respectively, or a salt thereof, as the hydrochloride or sulfate or phosphate, to give a compound of formula III wherein R
2
is methyl or ethyl;
(b2) or with hydroxylamine or a salt thereof, as the hydrochloride or sulfate or phosphate, or with hydroxylamin-O-sulfonic acid, to give a compound of formula III, wherein R
2
is hydrogen, and optionally converting this 1,2-dioxime with a methylating or ethylating agent respectively, for example with methyl iodide or dimethyl sulfate; or ethyl iodide or diethyl sulfate respectively, to give a compound of formula III, wherein R
2
is methyl or ethyl.
(a) Reacting a compound of formula IX, wherein the substituents are as defined for formula I, with nitrous acid or with an organic nitrite, e.g. a C
1
-C
6
alkyl nitrite such as pentyl nitrite, to give a compound of formula VIII;
(b) converting the compound of formula VIII with a methylating or ethylating agent respectively, for example with methyl iodide or dimethyl sulfate; or ethyl iodide or diethyl sulfate respectively, to give a compound of formula VI, wherein R
2
is methyl or ethyl;
(c) converting the compound of formula VI with hydroxylamine or a salt thereof, as the hydrochloride or sulfate or phosphate, or with hydroxylamin-O-sulfonic acid, to give a compound of formula III.
Compounds of formula VII and IX are known or may be prepared by known methods. The compounds of formula I can be used in the agricultural sector and related fields preventively and/or curatively as active ingredients in the control of plant diseases. The compounds of formula I according to the invention are distinguished by having good activity even at low rates of concentration, by being well tolerated by plants and by being environmentally friendly. They possess very advantageous, especially systemic, properties and can be used for the protection of a large number of cultivated plants. With the compounds of formula I it is possible to inhibit or destroy the pests that occur on plants or on parts of plants (the fruit, blossom, leaves, stems, tubers or roots) of various crops of useful plants, while parts of plants that grow later are also protected against phytopathogenic microorganisms, in particular fungi.
The compounds I can also be used as dressings in the treatment of seed (fruit, tubers, grains) and plant cuttings to provide protection against fungus infections as well as against phytopathogenic fungi that occur in the soil.
The compounds I are effective, for example, against phytopathogenic fungi belonging to the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, He dimethyl sulfate Iminthosporium, Fusarium, Septoria, Cercospora und Alternaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e.g. Phytophthora, Pythium, Plasmopara).
Within the scope of the invention, target crops for plant protection use include, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related crops); beet (sugar beet and fodder beet); pomes, stone fruit 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, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocados, cinnamon, camphor); and plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.
The compounds I are usually used in the form of compositions and can be applied to the area or plant to be treated simultaneously or in succession with further active ingredients. These further active ingredients may be, for example, fertilisers, micronutrient donors or other preparations that influence plant growth. It is also possible to use selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology. Suitable carriers and adjuvants may be solid or liquid and are the substances usefully employed in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilisers.
A preferred method of applying a compound of formula I, or an agrochemical composition comprising at least one of those compounds, is application to the foliage of the plants (foliar application). The frequency and the rate of application depend upon the risk of infestation by the pathogen in question. However, the compounds
Trah Stephan
Ziegler Hugo
Bayer Aktiengsellschaft
Gil Joseph C.
Henderson Richard E. L.
Mrozinski John E.
Richter Johann
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