Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-11-12
2002-11-12
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S063000, C514S383000, C514S399000
Reexamination Certificate
active
06479511
ABSTRACT:
This application is a 371 of PCT/EP98/02841, filed May 13, 1998.
The present invention relates to novel fungicidal compositions for the treatment of phytopathogenic diseases of crop plants, especially phytopathogenic fungi, and to a method of combatting phytopathogenic diseases on crop plants.
It is known that certain phenoxyquinoline derivatives have biological activity against phytopathogenic fungi, e.g. from EP-A-0326330 where their properties and methods of preparation are described. On the other hand azole fungicides, morpholines and aminopyrimidines are widely known as plant fungicides for application in various crops of cultivated plants. However, crop tolerance and activity against phytopathogenic plant fungi do not always satisfy the needs of agricultural practice in many incidents and aspects.
It has now been found that the use of
a) a 4-phenoxyquinoline of formula I
in association with
b) either an azole fungicide of formula II
wherein
A is selected from
whereby the &bgr;-carbon attaches to benzene ring of formula I, and wherein
R
1
is H, F, Cl, 4-fluorophenoxy or 4-chlorophenoxy;
R
2
is H, Cl or F;
R
3
and R
4
are independently H or CH
3
;
R
5
is C
1-4
alkyl or cyclopropyl;
R
6
is 4-chlorophenyl or 4-fluorophenyl;
R
7
is phenyl, and
R
8
is allyloxy, C
1-4
alkyl, or 1,1,2,2-tetrafluoroethoxy-methyl, and the salts of such azole fungicide;
or a morpholine fungicide of formula III
wherein
R
8
is C
8-15
cycloalkyl, C
8-15
alkyl, or C
1-4
alkylphenyl-C
1-4
alkyl,
and the salts of such morpholine fungicide;
or a compound of formula IV
or a compound of formula V
or a compound of formula VI
or a compound of formula VII
wherein R
10
is methyl or cyclopropyl;
or prochloraz;
is particularly effective in combatting or preventing fungal diseases of crop plants. These combinations exhibit synergistic fungicidal activity.
The combinations according to the invention may also comprise more than one of the active components b), if broadening of the spectrum of disease controll is desired.
Salts of the azole and morpholine active ingredients are prepared by reaction with acids, e.g., hydrohalo acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, or sulfuric acid, phosphoric acid or nitric acid, or organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzensulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, salicylic acid, p-aminosalicylic acid and 1,2-naphthalenedisulfonic acid.
The active ingredient combinations are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerelia, Uncinula); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, (Septoria, Cercospora, Alternaria, Pyricularia and
Pseudocercosporella herpotrichoides
(Tapesia ssp.)); Oomycetes (e.g. Phytophthora, Peronospora, Bremia, Pythium, Plasmopara).
Target crops for the areas of indication disclosed herein comprise within the scope of this invention e.g. the following species of plants: cereals (wheat, barley, rye, oats, rice, 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 black-berries); 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); or plants such as maize, tobacco, nuts, coffee, sugar cane, tea, vines, hops, bananas and natural rubber plants, as well as ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers). This list does not represent any limitation.
The combinations according to the present invention are particularly effective against powdery mildews and rusts, Rhynchosporium and Pyrenophora, and leptosphaeria fungi, in particular against pathogens of monocotyledoneous plants such as cereals, including wheat and barley.
The amount of combination of the invention to be applied, will depend on various factors such as the compound employed, the subject of the treatment (plant, soil, seed), the type of treatment (e.g. spraying, dusting, seed dressing), the purpose of the treatment (prophylactic or therapeutic), the type of fungi to be treated and the application time.
Particularly preferred mixing partners of the compunds of formula II are those in which R
1
is Cl, R
2
and R
3
are H, R
4
is CH
3
and R
5
is cyclopropyl and A is the moiety (i) (commonly known as cyproconazole); those wherein R
1
and R
2
are Cl, R
3
and R
4
are H, R
5
is propyl and A is the moiety (i) (commonly known as hexaconazole); those in which R
1
is 4-chlorophenoxy, R
2
is Cl, R
3
, R
4
and R
5
are H and A is the moiety (ii) (commonly known as difenoconazole); those in which R
1
and R
2
are Cl, R
3
and R
4
are H, R
5
is ethyl and A is the moiety (ii) (commonly known as etaconazole); those in which R
1
and R
2
are Cl, R
3
and R
4
are H, R
5
is propyl and A is the moiety (ii) (commonly known as propiconazole); those in which R
1
is Cl, R
2
is H, R
3
, R
4
and R
5
are CH
3
and A is the moiety (iii) (commonly known as tebuconazole); those in which R
1
is Cl, R
2
is H and A is the moiety (iv) (commonly known as triticonazole); those in which R
1
is H, R
2
is F, R
6
is 4-fluorophenyl and A is the moiety (v) (commonly known as flutriafol); those in which R
1
is H, R
2
is Cl, R
6
is 4-fluorophenyl and A is the moiety (vi) (commonly known as epoxiconazole); those in which R
1
is Cl, R
2
is H, R
7
is phenyl and A is the moiety (vii) (commonly known as fenbuconazole); those in which R
1
and R
2
are Cl, and A is the moiety (viii) (commonly known as bromuconazole); those in which R
1
and R
2
are Cl, R
8
is propyl and A is the moiety (ix) (commonly known as penconazole); those in which R
1
and R
2
are Cl, R
8
is allyloxy and A is the moiety (ix) (commonly known as imazalil); and those in which R
1
and R
2
are Cl, R
8
is 1,1,2,2-tetrafluoroethoxymethyl and A is the moiety (ix) (commonly known as tetraconazole); those wherein R
1
is F, R
2
is H, R
5
is CH
3
, R
6
is 4-fluorophenyl, and A is the moiety (x) (commonly known as flusilazole); and those in which R
1
is chloro, R
2
is hydrogen, R
3
and R
4
are methyl and A is the moiety (xi) (commonly known as metconazole). From this group propiconazole, difenoconazole, penconazole and cyproconazole are of particular interest as prefered embodiments of this invention.
Particularly preferred mixing partners of the compounds of formula III are those wherein R
8
is cyclododecyl (commonly known as dodemorph), or C
10-13
alkyl (commonly known as tridemorph), or 3-(4-tert-butylphenyl)-2-methylpropyl (commonly known as fenpropimorph). Predominantly, the cis-positioning of the methyl groups at the morpholine ring is present in the compounds of formula III when used in the combinations of the invention.
The compound of formual IV is commonly known as spiroxamine.
The compound of formula V is commonly known as fenpropidine.
The compound of formula VI is commonly known as dimethomorph.
The compounds of formula VII wherein R
10
is methyl is commonly known as pyrimethanil, and wherein R
10
is cyclopropyl is commonly known as cyprodinil.
The specific compounds b) mentioned in the preceding paragraphs are commercially available. Other compounds falling under the scope of the various groups of component b) are obtainable according to procedures analogous to those known for preparing the commercially available compounds.
It has
Knauf-Beiter Gertrude
Speich Jürg
Robinson Allen J.
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
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