Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2003-03-11
2004-09-14
Pryor, Alton N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06790851
ABSTRACT:
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 combating phytopathogenic diseases on crop plants.
It is known that certain substituted benzophenone derivatives have biological activity with high systemicity against phytopathogenic fungi, e.g. known from EP-A-897904, EP-A-899255 and EP-A-967196 where their properties and methods of preparation are described. On the other hand certain strobilurin derivatives, cyanoimidazole and carbonic acid amide compounds are known from the literature as plant fungicides for application in various crops of cultivated plants. However, crop tolerance and activity against phytopathogenic plant fungi of the known compounds 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 benzophenone of formula I
wherein
R
1
is methoxy, methyl, hydroxy, acetoxy or pivaloyloxy,
R
2
is C
1
-C
4
alkoxy or 2-halogenbenzyloxy,
R
3
is C
1
-C
4
alkoxy,
R
4
is C
1
-C
4
alkyl, halogen or trifluoromethyl, and
R
5
is hydrogen, halogen, C
1
-C
4
alkoxy, trifluoromethyl or nitro; in association with
b) the strobilurin of formula II
is particularly effective in combating or preventing fungal diseases of crop plants. These combinations exhibit synergistic fungicidal activity.
The compounds of formula I are known from EP-A-897904, EP-A-899255 and EP-A-967196. Specific examples of preferred individual compounds are listed in the following table.
No.
R
1
R
2
R
3
R
4
R
5
1.01
OCH
3
OCH
3
OCH
3
CH
3
Br
1.02
OCH
3
OCH
3
OCH
3
CH
3
Cl
1.03
OCH
3
OC
2
H
5
OCH
3
CH
3
Cl
1.04
OCH
3
OC
3
H
7
-n
OCH
3
CH
3
Cl
1.05
OCH
3
OCH
3
OCH
3
CH
3
CF
3
1.06
OCH
3
OCH
3
OCH
3
Cl
H
1.07
OCH
3
OCH
3
OCH
3
CF
3
H
1.08
OCH
3
OCH
3
OCH
3
CH
3
H
1.09
OCH
3
OCH
3
OCH
3
Cl
Br
1.10
OCH
3
OCH
3
OCH
3
Cl
CH
3
1.11
CH
3
OCH
3
OCH
3
CH
3
Cl
1.12
CH
3
OCH
3
OCH
3
CH
3
Br
1.13
CH
3
OCH
3
OCH
3
CH
3
NO
2
1.14
CH
3
OCH
3
OCH
3
CH
3
OCH
3
1.15
CH
3
OCH
3
OC
4
H
9
-n
CH
3
Cl
1.16
CH
3
OCH
3
OC
4
H
9
-n
CH
3
Br
1.17
CH
3
OCH
3
OC
4
H
9
-n
CH
3
NO
2
1.18
CH
3
OCH
3
OC
4
H
9
-n
CH
3
OCH
3
1.19
CH
3
—OCH
2
-2-
OC
4
H
9
-n
CH
3
Cl
F—C
6
H
4
1.20
CH
3
—OCH
2
-2-
OC
4
H
9
-n
CH
3
Br
F—C
6
H
4
1.21
CH
3
—OCH
2
-2-
OC
4
H
9
-n
CH
3
NO
2
F—C
6
H
4
1.22
CH
3
—OCH
2
-2-
OC
4
H
9
-n
CH
3
OCH
3
F—C
6
H
4
1.23
OH
OCH
3
OCH
3
CH
3
H
1.24
CH
3
—CO—O—
OCH
3
OCH
3
CH
3
H
1.25
OH
OCH
3
OCH
3
CH
3
Br
1.26
CH
3
—CO—O—
OCH
3
OCH
3
CH
3
Br
1.27
OH
OCH
3
OCH
3
CH
3
Cl
1.28
CH
3
—CO—O—
OCH
3
OCH
3
CH
3
Cl
1.29
(CH
3
)
3
C—CO—O—
OCH
3
OCH
3
CH
3
Br
The chemical designation of the above listed compounds is as follows:
1.01 5-bromo-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.02 5-chloro-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.03 5-chloro-6,6′-dimethyl-3′-ethoxy-2,2′,4′-trimethoxy-benzophenone,
1.04 5-chloro-6,6′-dimethyl-3′-propoxy-2,2′,4′-trimethoxy-benzophenone,
1.05 5-trifluoromethyl-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.06 6-chloro-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.07 6-trifluoromethyl-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.08 6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.09 5-bromo-6-chloro-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.10 6-chloro-5,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone,
1.11 5-chloro-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone,
1.12 5-bromo-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone,
1.13 5-nitro-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone,
1.14 2,6,6′-trimethyl-5,2′,3′,4′-tetramethoxy-benzophenone,
1.15 5-chloro-2,6,6′-trimethyl-2′-butoxy-3′,4′-dimethoxy-benzophenone,
1.16 5-bromo-2,6,6′-trimethyl-2′-butoxy-3′,4′-dimethoxy-benzophenone,
1.17 5-nitro-2,6,6′-trimethyl-2′-butoxy-3′,4′-dimethoxy-benzophenone,
1.18 2,6,6′-trimethyl-2′-butoxy-5,3′,4′-trimethoxy-benzophenone,
1.19 5-chloro-2,6,6′-trimethyl-2′-(o-fluorobenzyloxy)-3′,4′-dimethoxy-benzophenone,
1.20 5-bromo-2,6,6′-trimethyl-2′-(o-fluorobenzyloxy)-3′,4′-dimethoxy-benzophenone,
1.21 5-nitro-2,6,6′-trimethyl-2′-(o-fluorobenzyloxy)-3′,4′-dimethoxy-benzophenone,
1.22 2,6,6′-trimethyl-2′-(o-fluorobenzyloxy)-5,3′,4′-trimethoxy-benzophenone,
1.23 6,6′-dimethyl-2-hydroxy-2′,3′,4′-trimethoxy-benzophenone,
1.24 6,6′-dimethyl-2-acetoxy-2′,3′,4′-trimethoxy-benzophenone,
1.25 5-bromo-6,6′-dimethyl-2-hydroxy-2′,3′,4′-trimethoxy-benzophenone,
1.26 5-bromo-6,6′-dimethyl-2-acetoxy-2′,3′,4′-trimethoxy-benzophenone,
1.27 5-chloro-6,6′-dimethyl-2-hydroxy-2′,3′,4′-trimethoxy-benzophenone,
1.28 5-chloro-6,6′-dimethyl-2-acetoxy-2′,3′,4′-trimethoxy-benzophenone, and
1.29 5-bromo-6,6′-dimethyl-2-pivaloyloxy-2′,3′,4′-trimethoxy-benzophenone.
The compound of formula II is known from the literature under common name azoxystrobin, code ICIA5504, e.g. from EP-A-382375.
Among these mixtures those are preferred in which the compound of formula I is one of the compounds 1.01, 1.06, 1.07, 1.08, 1.09, 1.10, 1.11, 1.12, 1.13, 1.14, 1.25, 1.26 or 1.27.
Throughout this document the expression combination stands for the various combinations of components a) and b), e.g. in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, e.g. a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, e.g. a few hours or days. The order of applying the components a) and b) is not essential for working the present invention.
The combinations according to the invention may also comprise more than one of the active components a), 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 a) with the compound of formula II.
The active ingredient combinations are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, 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). T
Allen Rose M.
Pryor Alton N.
Syngenta Crop Protection Inc.
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