Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-31
2002-07-02
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...
C514S422000, C514S427000
Reexamination Certificate
active
06413973
ABSTRACT:
The present invention relates to novel fungicidal compositions for the treatment of phytopathogenic diseases of crop plants and against infestation on propagation stock of plants or on other vegetable material, especially phytopathogenic fungi, and to a method of combating phytopathogenic diseases on crop plants or for seed dressing.
It is known that certain pyrimidin-4-one derivatives have biological activity against phytopathogenic fungi, e.g. known from WO 97/02262 where their properties and methods of preparation are described. On the other hand azole fungicides, phthalimides, phenylamides, 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 pyrimidin-4-one of formula I
wherein
R
1
is hydrogen or halogen,
R
2
is hydrogen or halogen, and at least one of R
1
and R
2
is different from hydrogen;
R
22
is C
1
-C
5
alkyl or —CH
2
-cyclopropyl and
R
23
is C
1
-C
5
alkyl or —CH
2
-cyclopropyl;
in association with
b) either an anilinopyrimidine of formula II
wherein
R
3
is methyl, 1-propynyl or cyclopropyl;
or an azole of formula III
wherein
A is selected from
whereby the &bgr;-carbon attaches to benzene ring of formula III, and wherein R
4
is H, F, Cl, phenyl, 4-fluorophenoxy or 4-chlorophenoxy;
R
5
is H, Cl or F;
R
6
and R
7
are independently H or CH
3
;
R
8
is C
1-4
alkyl or cyclopropyl;
R
9
is 4-chlorophenyl or 4-fluorophenyl; and
R
11
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 IV
wherein
R
12
is C
8-15
cycloalkyl, and the salts of such morpholine fungicide;
or a strobilurin compound of formula V
wherein
X is O,
Y is N, and
R
13
is 4-(3-trifluoromethylphenyl)-3-aza-2-oxa-3-pentenyl;
or a pyrrole compound of the formula VI
wherein
R
14
and R
15
are independently halo, or together from a perhalomethylendioxo bridge;
or a phenylamide of the formula VII
wherein
R
16
is benzyl, methoxymethyl, 2-furanyl, chloromethyl or
R
17
is 1-methoxycarbonyl-ethyl, or
Z is CH or N,
R
20
is hydrogen or methyl,
R
21
is hydrogen or methyl;
or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram and zineb;
or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate and oxine-copper;
or sulfur;
or a phthalimide compound of the formula VIII
wherein
R
18
and R
19
together form a 4-membered bridge —CH
2
—CH═CH—CH
2
— or ═CH—CH═CH—CH═;
or with compound of formula IX
or with a compound of formula X
or with a compound of formula XI
or with a compound of formula XII
or with a compound of formula XIII
or with a compound of formula XIV
or with a compound of formula XV
or with a compound of formula XVI
or with a compound of formula XVII
or with a compound of formula XIX
or with a compound of formula XX
or with a compound of formula XXI
or with a compound of formula XXIII
or with a compound of formula XXIV
or with a compound of formula XXV
or with a compound of formula XXVI
or with a compound of formula XXVII
or with a compound of formula XXVIII
wherein
n is 0 or 1 or 2 etc, and
R is hydrogen or —C(═NH)NH
2
;
is particularly effective in combating 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 control is desired. For instance, it may be advantageous in the agricultural practice to combine two or three components b) with the any of the compounds of formula I, or with any preferred member of the group of compounds of formula I.
From WO 97/02262 the following specific species of formula I are known:
Comp.No.
R
1
R
2
R
22
R
23
I.1
Cl
H
n-propyl
n-propyl
I.2
Br
H
n-propyl
n-propyl
I.3
H
Cl
n-propyl
n-propyl
I.4
H
Br
n-propyl
n-propyl
I.5
Cl
H
n-butyl
n-propyl
I.6
Br
H
n-butyl
n-propyl
I.7
H
Cl
n-butyl
n-propyl
I.8
H
Br
n-butyl
n-propyl
I.9
Cl
H
i-butyl
n-propyl
I.10
Br
H
i-butyl
n-propyl
I.11
Cl
H
n-propyl
i-butyl
I.12
Br
H
n-propyl
i-butyl
I.13
Cl
H
—CH
2
-cyclopropyl
n-propyl
I.14
Br
H
—CH
2
-cyclopropyl
n-propyl
I.15
H
Cl
—CH
2
-cyclopropyl
n-propyl
I.16
H
Br
—CH
2
-cyclopropyl
n-propyl
I.17
Cl
H
n-propyl
—CH
2
-cyclopropyl
I.18
Br
H
n-propyl
—CH
2
-cyclopropyl
A preferred embodiment of the present invention is represented by those combination which comprise as component a) a compound of the formula I wherein R
1
is chloro or bromo, R
2
is chloro or bromo, R
22
is n-propyl, n-butyl, i-butyl and R
23
is n-propyl, n-butyl, i-butyl.
Among the mixtures of present invention most preference is given to the mixture of compounds 6-chloro-3-n-propyl-2-n-propyloxy-4-(3H)-quinazolinone (compound I.1), 6-bromo-3-n-propyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.2), 7-chloro-3-n-propyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.3), 7-bromo-3-n-propyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.4), 6-chloro-3-n-butyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.5), 6-bromo-3-n-butyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.6), 7-chloro-3-n-butyl-2-n-propyloxy-4-(3H)-quinazolinone (compound I.7), 7-bromo-3-n-butyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.8), 6-chloro-3-i-butyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.9) and 6-bromo-3-i-butyl-2-n-proplyoxy-4-(3H)-quinazolinone (compound I.10) with the compounds of component b), especially the commercially available products falling within the given ranges, i.e. the commercial products mentioned throughout this document.
Salts of the azole, amine 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-naphtalenedisulfonic acid.
The active ingredient combinations are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Sclerotinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Tilletia, Puccinia); Fungi imperfecti (e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella herpotrichoides); 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, turf, bananas and natural rubber plants, as well as ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers) and their seeds. This list does not represent any limitation.
The co
Hermann Dietrich
Knauf-Beiter Gertrude
Müller Kaspar
Walter Harald
Allen Rose M.
Robinson Allen J.
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
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