Fungicidal compositions

Details Fungicidal compositions Fungicidal compositions

2002-01-18

2002-10-29

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S676000, C514S687000

Reexamination Certificate

active

06472429

ABSTRACT:

FIELD OF THE INVENTION
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.
BACKGROUND OF THE INVENTION
It is known that (E,E)-&agr;-(methoxyimino)-2-[[[[1-(phenyl) ethylidene]amino]oxy]methyl]-benzeneacetic acid methyl ester derivatives have biological activity against phytopathogenic fungi, e.g. known from EP-A-460575 where their properties and methods of preparation are described. On the other hand certain substituted benzophenone compounds with high systemicity are known from EP-A-899255 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.
DETAILED DESCRIPTION
It has now been found that the use of
a) (E,E)-&agr;-(methoxyimino)-2-[[[[1-[3(trifluoromethyl) phenyl] ethylidene]amino]oxy]methyl]-benzeneacetic acid methyl ester of formula I
 in association with
b) a benzophenone of formula II
 wherein
R
1
is hydrogen, halogen, C
1-4
alkoxy or NO
2
; and
R
2
is C
1-6
alkyl or optionally substituted benzyl;
is particularly effective in combating or preventing fungal diseases of crop plants. These combinations exhibit synergistic fungicidal activity.
In the above definitions C
1-4
alkoxy denotes preferably methoxy, ethoxy, n-propoxy or i-propoxy, with methoxy being preferred. C
1-6
alkyl designates straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, or the possible pentyl or hexyl isomers. Preferred are methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl. Halogen stands for fluorine, chlorine, bromine and iodine with chlorine and bromine being preferred.
Substitutents of the optionally substituted benzyl group are placed on the phenyl ring with one or two substituents being present and being preferably independently selected from the group comprising halogen or C
1-5
alkyl. More preferred substitution patterns are 2-methylbenzyl and 2-halobenzyl, e.g. 2-chlorobenzyl and 2-fluorobenzyl.
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 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 EP-A-899255 the following specific species of formula II are known:
No.
R
1
R
2
01
Br
CH
3
02
Br
n-C
4
H
9
03
NO
2
CH
3
04
OCH
3
CH
3
05
Cl
CH
3
06
Br
n-C
5
H
11
07
Br
n-C
3
H
7
08
Br
benzyl
09
Br
C
2
H
5
10
H
benzyl
11
H
3,5-F
2
-benzyl
12
H
3,4-F
2
-benzyl
13
H
2,5-F
2
-benzyl
14
H
2,3-F
2
-benzyl
15
H
2,4-F
2
-benzyl
16
H
2,6-F
2
-benzyl
17
H
2-F-benzyl
18
H
3-F-benzyl
19
H
4-F-benzyl
20
H
2,6-Cl
2
-benzyl
21
H
3,4-Cl
2
-benzyl
22
H
2,4-Cl
2
-benzyl
23
H
2-Cl-benzyl
24
H
3-Cl-benzyl
25
H
4-Cl-benzyl
26
H
3-Cl-2-F-benzyl
27
H
2-Cl-6-F-benzyl
28
H
2-CH
3
-benzyl
29
H
3-CH
3
-benzyl
30
H
4-CH
3
-benzyl
31
H
2-OCH
3
-benzyl
32
H
3-OCH
3
-benzy
33
H
4-OCH
3
-benzyl
34
H
4-tert-C
4
H
9
-benzyl
35
H
2,4-(CH
3
)
2
-benzyl
36
H
2,5-(CH
3
)
2
-benzyl
37
H
3-CF
3
-benzyl
38
H
4-CF
3
-benzyl
39
H
2-Br-benzyl
40
H
3-Br-benzyl
41
H
4-Br-benzyl
42
H
i-C
5
H
11
43
H
n-C
4
H
9
44
H
n-C
5
H
11
A preferred embodiment of the present invention is represented by those combinations which comprise as component b) the following subgroups are preferred synergistic partners to the compound of formula I:
compounds of formula II wherein R
1
is hydrogen, halogen, methoxy or NO
2
and R
2
is C
1-6
alkyl or optionally substituted benzyl; or
compounds of formula II wherein R
1
is bromine, chlorine, methoxy or NO
2
and R
2
is C
1-6
alkyl or optionally substituted benzyl; or
compounds of formula II wherein R
1
is bromine or chlorine, methoxy or NO
2
and R
2
is methyl, n-butyl or 2-F-benzyl; or
compounds of formula II wherein R
1
is bromine and R
2
is methyl, n-butyl or 2-F-benzyl.
Preferred individual compounds of formula II are
3-bromo-2′-butoxy-3′,4′-dimethoxy-2,6,6′-trimethyl-benzophenone, and
3-chloro-2′-butoxy-3′,4′-dimethoxy-2,6,6′-trimethyl-benzophenone.
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, Pucinia); 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). This list does not represent any limitation.
The combinations of the present invention may also be used in the area of protecting technical material against attack of fungi. Technical areas include wood, paper, leather, constructions, cooling and heating systems, ventilation and air conditioning systems, and the like. The combinations according the present invention can prevent the disadvantageous effects such as decay, discoloration or mold.
The combinations according to the present invention are particularly effective against powdery mildews and rusts, pyrenophora, rhynchosporium, tapesia, fusarium and leptosphaeria fungi, in particular against pathogens of monocotyledonous plants such as cereals, including wheat and barley. They are furthermore particularly effective against downy mildew species, powdery mildews, leaf spot diseases and rusts in dicotyledonous plants.
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.
It has been found that the use of compounds of formula II in combination with the compound of formula I surprisingly and substantially enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the method of

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