US3484525A - Process of controlling fungi with 1,3-diaryl-imino-hydantoins - Google Patents

Description

United States Patent Int. Cl. A01n 9/22 US. Cl. 424-273 Claims ABSTRACT OF THE DISCLOSURE The process of controlling fungi with 1,3-di-aryl-5- iminohydantoins of structure O= =NH R- N-R where R is aryl, haloaryl, nitroaryl, or lower alkyl substituted aryl.

This invention relates to the use of 1,3-diaryl-5-iminohydantoins as fungicides and is particularly concerned with their use against fungi attacking plants.

The active agents used in the invention are those having the structural formula where R is aryl, haloaryl, nitroaryl, or lower alkyl substituted aryl. More specifically, the R groups can be phenyl, naphthyl, chlorophenyl, nitrophenyl, chloronaphthyl, fluorophenyl, etc., and the lower alkyl substituted aryl groups may be methylphenyl, ethylphenyl, propylphenyl, butylphenyl, 2 ethylnaphthyl, S-methylnaphthyl and the like. It will be further understood that the halo, nitro and alkyl substituents on the aryl ring may be in any position.

The active compounds may be made by the procedure set forth by Tad L. Patton which appear in the Journal of Organic Chemistry, vol. 32, p. 383, (1967).

The active agents described above may be used in accordance with the usual procedures where fungistatic and fungicidal activityis desired. For example, they may be used for treating seeds, plants and fruits to prevent or control attack by fungi. One of the advantages of the compounds is that they may be used under controlling conditions without being toxic to the treated plants. The compounds will be useful in controlling numerous fungi affecting fruits, vegetable and crop plants, including powdery mildew, late blight, apple scab and other fruit fungal diseases.

The procedures which will be used for applying the fungicidal compositions to plants will be in accord with the usual practices known in the art. Since the active compounds are insoluble in water, they will generally be applied to the plant as an aqueous dispersion which is preferably obtained from a wettable powder. In a preferred embodiment of the invention, a concentrated reactive agent together with a carrier containing a surfactant will be manufactured and sold as an article of commerce. Preferably, this concentrate will be in the form of a wettable powder made simply by blending the active agent with a carrier such as clay or other finely-divided or particulate inert matter, for example attapulgite, bentonite, fullers earth, and the like. As a surfactant there may be used one or more of the many surface active agents gen- 3,484,525 Patented Dec. 16, 1969 erally employed such as a naphthalene sulfonic acid, a lignosulfonate, or the various other cationic, anionic and non-ionic surfactants available for such purposes. Generally, the wettable powder concentrate will contain from about 5% to about by weight of the active agent, the balance being the carrier and the surfactant.

Alternatively, the active agents may be formulated in organic solvent systems with a solution or emulsion concentrate containing from 5% to about 90% by weight of active agent and the organic solvent system dispersed in water just prior to use. Generally, the organic material will be an organic hydrocarbon solvent such as xylene, toluene, and the like, but other solvent systems such as ketones (methyl ethyl ketone, and acetone, etc.), aliphatic amides such as dimethyl formamide, dimethyl acetamide, ketoalcohols (diacetone alcohol) and the like may be also used.

The rate of application of the fungicides onto the plant, flower, seed or other crop to be treated will be an inhibiting amount and will employ formulations containing from about 0.5 lbs./ gallons to about 10 lbs./ 100 gallons of formulated material. Preferably, for economic reasons, the rate of application will be from about 0.25 lbs. to about 3 lbs. of active agent per acre of plant or from 0.25 lbs. to 8 lbs. per gallon of spray for tree application. Application is made in the usual manner by spraying an aqueous dispersion of the agent onto the plant and treatment in this manner enables control of the fungi to be obtained.

In order to more fully illustrate the invention, the following examples are given:

Example l.--Formulations of active agent AAqueous dispersion:

10 parts by weight of l,3-phenyl-5-iminohydantoin and 90 parts by weight of water are ball-milled in the presence of an alkyl urea polyether alcohol surfactant until a stable dispersion is obtained.

B-Wettable powder:

Ingredients: Percent by weight l,3-di(3,4-dichlorophenyl)-5-iminohydantoin 50 Surfactants Sodium lignosulfonate (Marasperse N) 2 Alkylphenoxypoly(ethyleneoxyethanol) (Igepal-RC 760) Carrier (attapulgite) 46 Example 2.-Activity against powdery mildew Pinto beans plants in pots are sprayed with water emulsion of the active agents to deposit the agent at various concentrations. Powdery mildew (Erysiphe polgoni) cultures maintained on other plants are then used to inoculate the treated plants. Percent control is obtained by visual comparisons with a control test using none of the active agent.

An aqueous dispersion made from a concentrate of 10% of 1,3-di-(4-chlorophenyl)-5-iminohydantoin in xylene (45%), dimethylsulfoxide (20%), tetramethylurea (20%) and, as surfactant, Triton X (5%), gives 100% control of bean powdery mildew when applied as a 0.5% dispersion.

In like manner, 70% control is obtained with 1,3-di(4- methylphenyl) -5-iminohydantoin.

Example 3.Activity against late blight Three to four week old Bonny Best tomato seedlings are sprayed with a water emulsion of the active agent and inoculated (after drying) with a suspension of zoospores (produced from Sporangia from lima bean cultures of Phytopthora infestans). Counts are made of spots of late blight infection when they appear and control is expressed as percentage of control.

When applied at a rate of about 0.5 pounds per acre:

1,3-di(4 chlorophenyl)--iminohydantoin gives 100% control; at 0.5 lb./A.

1,3-diphenyl-S-iminohydantoin gives 100% control; at

0.5 lb./A.

1,3-di(2-chlorophenyl)-5-iminohydantoin gives 96% control; and at 1.0 lb./A.

1,3-di(4-methylphenyl)-5-iminohydantoin gives 87% control.

Example 4.Spore germination activity Spores from active cultures and the active agent are mixed together in a drop of Water contained in wax rings on 1" x 3" glass slides. The ratings indicated at what concentration germination occurs after 24 hours: 3+ equals none at 1 part per million, 3 equals 1 to parts per million, 2 equals 10 to 100 parts per million, 1 equals 100 to 1000 parts per million, 0 equals 1000 per million. The results are shown in the following table:

TABLE Agent:

1% R-bl NR V Alternaria Glomerella Monilim'a (U) bmssicolo cingulata fructicola R =4-chlorophenyl l 1 1 R=2-ehlorophenyl l l 1 R =4-n1ethylpheuyl 2 3 2 where R is phenyl, naphthyl, or halo-, nitroor lower alkyl-substituted phenyl or naphthyl.

2. The process of claim 1 where the active agent is 1,3-diphenyl-S-iminohydantoin.

3. The process of claim 1 Where the active agent is 1,3-di(4-chlorophenyl)-5-iminohydantoin.

4. The process of claim 1 where the active agent is 1,3-di 2-chlorophenyl) -5 -iminohydantoin.

5. The process of claim 1 where the active agent is 1,3-di 4-methylphenyl) -5 -iminohydantoin.

References Cited Patton: J. Org. Chen1., 32: 383-388, February 1967.

S. K. ROSE, Primary Examiner

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