Fungicidal compositions containing N-acetonylbenzamides

Details Fungicidal compositions containing N-acetonylbenzamides Fungicidal compositions containing N-acetonylbenzamides

2000-07-13

2002-03-05

Robinson, Allen (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S617000

Reexamination Certificate

active

06353020

ABSTRACT:

The present invention relates to new fungicidal compositions and their use as a method for controlling phytopathogenic fungi on plants.
It is always desirable to improve products which can be used by growers in order to combat fungal diseases of crops, and in particular diseases caused by fungi in the class Oomycetes.
It is also always desirable to reduce the doses of chemical products spread into the environment to combat fungal attacks on crops, in particular by reducing the application doses of the products.
It is also always desirable to increase the number of antifungal products available to growers in order that they will find, among these products, the one which is best suited to the grower's specific use.
One objective of the invention is thus to provide novel fungicidal compositions which are useful against the problems outlined above.
Another objective of the invention is to propose novel fungicidal compositions which are useful in the preventive and curative treatment of diseases caused by fungi of the class Oomycetes.
Still another objective of the invention is to propose novel fungicidal compositions which are of improved efficacy against mildew and/or late blight caused by Oomycetes.
Yet another objective of the invention is to propose novel fungicidal compositions which are of improved efficacy against downy mildew in grapes and other crops and/or late blight in tomatoes and potatoes.
It has now been found that these objectives may be achieved, partly or totally, by means of the fungicidal compositions according to the present invention.
U.S. Pat. Nos. 5,304,572 and 5,677,333 disclose applying mixtures of the N-acetonylbenzamides disclosed therein with other fungicidal compounds. It has now been discovered that application of the N-acetonylbenzamides disclosed in these patents in combination with selected other fungicidal compounds provides unexpectedly high fungicidal activity and is effective in controlling phytopathogenic fungi at lower N-acetonylbenzamide dosage rates than those disclosed in the U.S. Pat. No. 5,304,572. Although U.S. Pat. No. 5,677,333 discloses the use of N-acetonylbenzamides in combination with ethylene bisdithiocarbamates, cymoxanil and dimethomorph to provide unexpectedly high fungicidal activity, the synergistic combinations of this invention are not disclosed or suggested in that patent.
In a first embodiment of this invention, there is provided a composition comprising
(a) a fungicidally effective amount of a first fungicidally active compound having the formula (I)
 or an agronomically acceptable salt thereof
wherein
R
1
and R
3
are each independently halo or (C
1
-C
4
)alkyl,
R
2
is (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
4
)alkoxy or cyano,
R
4
and R
5
are each independently a hydrogen atom or (C
1
-C
4
)alkyl, provided that at least one of R
4
and R
5
is (C
2
-C
4
)alkyl and
X is halo, thiocyano or isothiocyano;
(b) a fungicidally effective amount of a second fungicidally active compound which is an acylalanine type fungicide such as the R-enantiomer of metalaxyl, the racemic mixture of metalaxyl, oxadixyl, furalaxyl, benalaxyl, ofurace and cyprofuram; and
(c) an agronomically acceptable carrier.
In a second embodiment of this invention, there is provided a method for controlling phytopathogenic fungi on a plant comprising the application of
(a) a fungicidally effective amount of a first fungicidally active compound having the formula (I)
 or an agronomically acceptable salt thereof
wherein
R
1
and R
3
are each independently halo or (C
1
-C
4
)alkyl,
R
2
is (C
1
-C
4
)alkyl, (C
2
-C
4
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
4
)alkoxy or cyano,
R
4
and R
5
are each independently a hydrogen atom or (C
1
-C
4
)alkyl, provided that at least one of R
4
and R
5
is (C
2
-C
4
)alkyl and
X is halo, thiocyano or isothiocyano;
(b) a fungicidally effective amount of a second fungicidally active compound which is an acylalanine type fungicide such as the R-enantiomer of metalaxyl, the racemic mixture of metalaxyl, oxadixyl, furalaxyl, benalaxyl, ofurace and cyprofuram; and
(c) an agronomically acceptable carrier to the plant seed, to the plant foliage or to the growth medium for the plant.
When R
4
and R
5
are different, optical enantiomers of the compounds of the present invention are possible due to the presence of an asymmetric carbon atom linking R
4
and R5. It is known that many biologically active compounds have optical enantiomers, one of which is more active than the other. Similarly, for compounds used in the method of the present invention, the biological activity of one enantiomer may exceed that of the other enantiomer, as described in EP 0 816 330 A1, Jan. 7, 1998.
“(C
1
-C
4
)alkyl” means a straight or branched alkyl group having one to four carbon atoms per group and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
“(C
2
-C
4
)alkenyl” means a straight or branched alkenyl group having two to four carbon atoms per group and includes, for example, ethenyl, 2-propenyl, 2-butenyl, 1-methylethenyl, 2-methyl-2-propenyl and the like.
“(C
2
-C
6
)alkynyl” means a straight or branched alkynyl group having from two to six carbons per group and includes, for example, ethynyl, 2-propynyl, 2-butynyl and the like.
“Halo” means chloro, fluoro, bromo and iodo.
“(C
1
-C
4
)alkoxy” means a straight or branched alkoxy group having one to four carbon atoms per group and includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy.
“Cyano” means a group having the structural formula —CN.
“Thiocyano” means a group having the structural formula —SCN.
“Isothiocyano” means a group having the structural formula —NCS.
Agronomically acceptable salts include, for example, metal salts such as sodium, potassium, calcium and magnesium salts, ammonium salts such as isopropyl ammonium salts and trialkylsulfonium salts such as triethylsulfonium salts.
The first fungicidally active compound may be a single compound of formula (I) or, alternatively, may be a mixture of compounds of formula (I). Suitable compounds of formula (I) include, but are not limited to,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-methylbenzamide,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-ethylbenzamide,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-ethoxybenzamide,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-methoxybenzamide,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-cyanobenzamide, and
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dibromo-4-methylbenzamide.
In a preferred embodiment, the first fungicidally active compound is
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-methylbenzamide,
N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dibromo-4-cyanobenzamide or
a mixture thereof.
More preferably, the N-acetonyl benzamide compound is N-[3′-(1′-chloro-3′-methyl-2′-oxopentan)]-3,5-dichloro-4-methylbenzamide.
Suitable compounds which function as the second fungicidally active compound include, but are not limited to, the R-enantiomer of metalaxyl, the racemic mixture of metalaxyl, oxadixyl, furalaxyl, benalaxyl, ofurace and cyprofuram.
In a preferred embodiment, the second fungicidally active compound is selected from the group consisting of the R-enantiomer of metalaxyl, oxadixyl, ofurace and benalaxyl.
The method of the present invention may optionally further comprise application of other compounds having biological activity, for example, additional fungicidally active compounds or compounds having herbicidal activity or insecticidal activity, to the plant seed, to the plant foliage or to the growth medium for the plant.
The method of the present invention is useful for

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