Method for controlling fungi using phenylhydrazine derivatives

Details Method for controlling fungi using phenylhydrazine derivatives Method for controlling fungi using phenylhydrazine derivatives

1999-09-07

2001-10-02

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

N-c doai

C514S478000, C514S482000, C514S485000, C514S488000, C514S614000

Reexamination Certificate

active

06297275

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a method for controlling fungi using certain phenylhydrazine derivatives. More particularly, this invention relates to a method for controlling fungi by contacting the fungi with a fungicidally effective amount of a phenylhydrazine derivative compound, or by applying the phenylhydrazine derivative compound to plant foliage or plant seed susceptible to attack by said fungi, or to a growth medium for the plant to be protected.
BACKGROUND OF THE INVENTION
U.S. Pat. No. 5,367,093 describes phenylhydrazine derivative compounds useful as insecticides, acaricides and nematocides. Japanese patent JP02300157 1990 (CA 115:226148) describes benzyl carbazates useful as agrochemical microbiocides. Japanese patent JP02295962 1990 (CA 114:138036) describes the preparation of phenyl carbazates useful as agrochemical fungicides. Japanese patent JP60161959 1985 (CA 104:33894) describes hydrazine carboxylates useful as fungicides. German patent DE2223936 1973 (CA 80:70557) describes fungicidal arylhydrazine derivatives.
It is an object of this invention to provide a novel method for controlling fungi using phenylhyrazine derivative compounds and compositions.
SUMMARY OF THE INVENTION
This invention relates to a method for controlling fungi, particularly phytopathogenic fungi, comprising contacting the fungi with a fungicidally effective amount of a phenylhydrazine derivative compound of the formula:
wherein:
X is a) phenyl; phenyl(C
1
-C
4
alkoxy); phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from halogen; C
1
-C
4
alkyl; and C
1
-C
4
alkylthio;
Y is H, C
1
-C
4
alkanoyl, C
1
-C
4
haloalkanoyl, or (C
1
-C
4
alkoxy)carbonyl; and
R is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, or phenyl (C
1
-C
4
alkoxy).
This invention also relates to a method for controlling fungi on a plant or plant seed which comprises applying to the plant or the plant seed, or to a growth medium or water in which the plant or plant seed is growing or is to be grown in, a fungicidally effective amount of a phenylhydrazine derivative compound of the formula:
wherein:
X is a) phenyl; phenyl(C
1
-C
4
alkoxy); phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from halogen; C
1
-C
4
alkyl; and C
1
-C
4
alkylthio;
Y is H, C
1
-C
4
alkanoyl, C
1
-C
4
haloalkanoyl, or (C
1
-C
4
alkoxy)carbonyl; and
R is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, or phenyl(C
1
-C
4
alkoxy).
DETAILED DESCRIPTION OF THE INVENTION
For the purposes of this invention, the term “controlling fungi” means inhibiting both future infestation and continued growth of existing infestations.
In the compounds useful in the method of this invention, X is preferably, a) phenyl, phenyl(C
1
-C
2
alkoxy), or phenoxy; or b) one substituent from group a) and one or more substituents selected from halogen; C
1
-C
2
alkyl; and C
1
-C
2
alkylthio;
Y is preferably H, C
1
-C
2
alkanoyl, C
1
-C
2
haloalkanoyl, or (C
1
-C
2
alkoxy)carbonyl; and
R is preferably H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, or phenyl(C
1
-C
2
alkoxy).
X is more preferably phenylmethoxy, phenoxy, or phenyl and halogen or C
1
-C
4
alkylthio, most preferably, phenoxy; Y is more preferably hydrogen or C
1
-C
2
haloalkanoyl, most preferably, hydrogen; and R is more preferably C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy, most preferably, C
1
-C
4
alkoxy.
The compounds useful in the method of this invention having the structure of formula I can be prepared by reacting a substituted phenylhydrazine of the formula:
with an acylating reagent of the formula:
wherein Z is halo or
and an equivalent of an HCl acceptor such as pyridine in a solvent such as toluene. The product of this reaction can be further acylated, or converted by oxidation with an oxidizing agent such as Pd/air to form compounds of the structure of formula II.
Compositions useful in the method of this invention comprise (a) a fungicidally effective of a compound having a structure of formula (I) or (II) above, and (b) a suitable carrier. Such suitable carriers may be solid or liquid in nature.
Suitable liquid carriers may be comprised of water, alcohols, ketones, phenols, toluene and xylenes. In such formulations, additives conventionally employed in the art may be utilized such as, for example, one or more surface active agents and/or inert diluents, to facilitate handling an application of the resulting pesticide composition.
The compositions useful in the method of this invention can alternatively comprise solid carriers taking the form of dusts, granules, wettable powders, pastes, aerosols, emulsions, emulsifiable concentrates, and water-soluble solids.
For example, the compounds useful in the method of this invention can be applied as dusts when admixed with or absorbed onto powdered solid carriers, such as mineral silicates, e.g., mica, talc, pyrophyllite and clays, together with a surface-active dispersing agent so that a wettable powder is obtained which then is applicable directly to the loci to be treated. Alternatively, the powdered solid carrier containing the compound admixed therewith may be dispersed in water to form a suspension for application in such form.
Granular formulations of the compounds, suitable for application by broadcasting, side dressing, soil incorporation or seed treatment, are suitably prepared using a granular or pellitized form of carrier such as granular clays, vermiculite, charcoal or corn cobs.
Alternatively, the compounds useful in the method of this invention can be applied in liquids or sprays when utilized in a liquid carrier, such as in a solution comprising a compatible solvent such as acetone, benzene, toluene or kerosene, or as dispersed in a suitable non-solvent medium, for example, water.
Another method of application to the loci to be treated is aerosol treatment, for which the compound may be dissolved in an aerosol carrier which is a liquid under pressure but which is a gas at ordinary temperature (e.g., 20° C.) and atmospheric pressure. Aerosol formulations may also be prepared by first dissolving the compound in a less volatile solvent and then admixing the resulting solution with a highly volatile liquid aerosol carrier.
For treatment of plants (such term including plant parts), the compounds useful in the method of this invention preferably are applied in aqueous emulsions containing a surface-active dispersing agent which may be non-ionic, cationic or anionic. Suitable surface-active agents include those known in the art, such as those disclosed in U.S. Pat. No. 2,547,724 (columns 3 and 4). The compounds of the invention may be mixed with such surface-active dispersing agents, with or without an organic solvent, as concentrates for the subsequent addition of water to yield aqueous suspensions of the compounds at desired concentration levels.
In addition, the compounds may be employed with carriers which are pesticidally active, such as insecticides, acaricides, fungicides or bactericides.
It will be understood that the amount of the compound in a given formulation useful in the method of this invention will depend upon the specific fungus to be combatted, as well as upon the specific chemical composition and formulation of the compound being employed, the method of applying the compound/formulation and the locus of treatment so that the fungicidally effective amount of the compound may vary widely. Generally, however, concentrations of the compound as the active ingredient in fungicidally effective formulations in the method of this invention can range from about 0.1 to about 95 percent by weight. Spray dilutions may be as low as a few parts per million, while at the opposite extreme, full strength concentrates of the compound may be usefully applied by ultra low volume techniques. Concentration per unit area, where plants constitute the loci of treatment, may range between about 0.01 and about 50 pounds per acr

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