Fungicidal combinations

Details Fungicidal combinations Fungicidal combinations

2001-11-29

2004-02-10

Pak, John (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S345000, C514S384000, C514S407000, C514S676000, C514S686000, C514S687000

Reexamination Certificate

active

06689776

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 and EP-A-899255 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 or methyl,
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 and EP-A-899255. Specific examples of preferred individual compounds are listed in the following table.
No.
R
1
R
2
R
3
R
4
R
5
I.01
OCH
3
OCH
3
OCH
3
CH
3
Br
I.02
OCH
3
OCH
3
OCH
3
CH
3
Cl
I.03
OCH
3
OC
2
H
5
OCH
3
CH
3
Cl
I.04
OCH
3
OC
3
H
7
-n
OCH
3
CH
3
Cl
I.05
OCH
3
OCH
3
OCH
3
CH
3
CF
3
I.06
OCH
3
OCH
3
OCH
3
Cl
H
I.07
OCH
3
OCH
3
OCH
3
CF
3
H
I.08
OCH
3
OCH
3
OCH
3
CH
3
H
I.09
OCH
3
OCH
3
OCH
3
Cl
Br
I.10
OCH
3
OCH
3
OCH
3
Cl
CH
3
I.11
CH
3
OCH
3
OCH
3
CH
3
Cl
I.12
CH
3
OCH
3
OCH
3
CH
3
Br
I.13
CH
3
OCH
3
OCH
3
CH
3
NO
2
I.14
CH
3
OCH
3
OCH
3
CH
3
OCH
3
I.15
CH
3
OCH
3
OC
4
H
9
-n
CH
3
Cl
I.16
CH
3
OCH
3
OC
4
H
9
-n
CH
3
Br
I.17
CH
3
OCH
3
OC
4
H
9
-n
CH
3
NO
2
I.18
CH
3
OCH
3
OC
4
H
9
-n
CH
3
OCH
3
I.19
CH
3
—OCH
2
-2-F—C
6
H
4
OC
4
H
9
-n
CH
3
Cl
I.20
CH
3
—OCH
2
-2-F—C
6
H
4
OC
4
H
9
-n
CH
3
Br
I.21
CH
3
—OCH
2
-2-F—C
6
H
4
OC
4
H
9
-n
CH
3
NO
2
I.22
CH
3
—OCH
2
-2-F—C
6
H
4
OC
4
H
9
-n
CH
3
OCH
3
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, and
1.22 2,6,6′-trimethyl-2′-(o-fluorobenzyloxy)-5,3′,4′-trimethoxy-benzophenone.
The compound of formula II is known from the literature under common name picoxystrobin, code ZNC 90160, e.g. from EP-A-278595.
The compound of formula III is known from the literature under code BAS 50001F, e.g. from WO 96/01256.
The compound of formula IV is known from the literature, e.g. from WO 96/36615.
The compound of formula V is known from the literature, e.g. from WO 95/04728.
The compound of formula VI is known from the literature under code IKF 916, e.g. from EP-A-705823.
The compound of formula VII is known from the literature under common name iprovalicarb, code SZX 722, e.g. EP-A-398072.
The compound of formula VIII is known from the literature under common name fenamidone, code RPA 407213, e.g. from EP-A-629616.
The compounds of formula IX are known from the literature, e.g. from WO 96/04252.
The compound of formula X is known from the literature under code RH 7281, e.g. from EP-A-600629.
The compound of formula XI is known from the literature under common name fenhexamide, code KBR 2738, e.g. from EP-A-339418.
Specifically, the combinations of this invention comprise
1) 5-bromo-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.01) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
2) 5-chloro-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.02) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
3) 5-chloro-6,6′-dimethyl-3′-ethoxy-2,2′,4′-trimethoxy-benzophenone (compound 1.03) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
4) 5-chloro-6,6′-dimethyl-3′-propoxy-2,2′,4′-trimethoxy-benzophenone (compound 1.04) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
5) 5-trifluoromethyl-6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.05) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
6) 6-chloro-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.06) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
7) 6-trifluoromethyl-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.07) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
8) 6,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.08) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
9) 5-bromo-6-chloro-6′-methyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.09) in combination with any of the compounds II, III, IV, V, VI, VIII, VIII, IX, X or XI,
10) 6-chloro-5,6′-dimethyl-2,2′,3′,4′-tetramethoxy-benzophenone (compound 1.10) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
11) 5-chloro-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone (compound 1.11) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
12) 5-bromo-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone (compound 1.12) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
13) 5-nitro-2,6,6′-trimethyl-2′,3′,4′-trimethoxy-benzophenone (compound 1.13) in combination with any of the compounds II, III, IV, V, VI, VII, VIII, IX, X or XI,
14) 2,6,6′-trimethyl-5,2′,3′,4′-tetramethoxy-benzophenone (com

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