Fungicidal-N-(3-halo-2,6-dinitro-4-trifluoromethylphenyl)-pyrrolidones having the formula: ##STR1## where X is a halogen, PA1 Y is oxygen or sulfur, and PA1 R is H or lower alkyl, of up to 4 carbon atoms, Are prepared by reacting a 2,4-dihalo-3,5-dinitrobenzotrifluoride with an alkali metal salt of a pyrrolidone. The compounds of the invention show good fungicidal activity, particularly against rice spot and tomato blight.

BACKGROUND OF THE DISCLOSURE 
1. Field of the Invention 
This invention relates to fungicidal compounds which are 
N-(substituted-phenyl)-pyrrolidones. 
2. Description of the Prior Art 
Aromatic compounds are known in the art as being useful agricultural 
chemicals. Accordingly, it is the object of this invention to provide new 
and useful compounds which exhibit good fungicidal activity. 
SUMMARY OF THE INVENTION 
The present invention provides 
fungicidal-N-(3-halo-2,6-dinitro-4-trifluoromethylphenyl)-pyrrolidones 
having the formula: 
##STR2## 
where X is a halogen, 
Y is oxygen or sulfur, and 
R is H or lower alkyl, of up to 4 carbon atoms. 
The compounds of this invention are prepared by reacting a 
2,4-dihalo-3,5-dinitrobenzotrifluoride with an alkali metal salt of a 
pyrrolidone. 
The N-(substituted-phenyl)-pyrrolidones described herein show good 
fungicidal activity, particularly against rice spot and tomato blight. 
DESCRIPTION OF THE PREFERRED EMBODIMENTS 
The compounds (III) of this invention are prepared by condensing a 
2,4-dihalo-3,5-dinitrobenzotrifluoride (I) with an alkali metal salt of a 
pyrrolidone (II), as follows: 
##STR3## 
where Hal is a halogen, M.sup.+ is an alkali metal, and X, Y and R are as 
previously defined. 
I is produced by dinitration of the corresponding dihalobenzotrifluoride 
compound in a mixture of nitric and sulfuric acids, as described in U.S. 
Pat. No. 3,586,725. II is prepared by reacting pyrrolidone with an alkali 
methoxide. 
The condensation reaction is carried out by stirring the reactants for an 
extended period of time at room temperature, in a suitable solvent, and 
then at an elevated temperature for an additional period of time. Upon 
completion of the reaction, the solvent is removed and the desired product 
is separated by partition extraction. The extraction agent then is removed 
by rotoevaporation and the product is crystallized from a suitable 
solvent. 
The compounds of this invention are especially useful as agricultural 
fungicides. Usually they are applied to the soil at the rate of about 1 to 
25 lbs. per acre or as a foliar spray at concentrations of about 31 to 260 
ppm. They show particularly effective foliar fungicidal activity against 
the following pathogens: blight of tomatoes and rice spot. 
The materials of the present invention may be applied to those fungus 
susceptible plants on site at a rate of about 1 or less to about 25 pounds 
per acre depending on various circumstances of the susceptibility to the 
fungus, the weather, the stage of growth and various other factors. The 
material may be applied as a dust or spray. As a dust it is more practical 
to extend it with diluents such as bentonite, chalk, clay, diatomaceous 
earth, fullers earth, mica, ground slate or any of the other usual 
carriers for agricultural chemicals. As a spray it may be incorporated 
into water as a solution. The higher molecular weight compounds may be 
dissolved first in a solvent, such as an alcohol, or a petroleum fraction, 
such as isoparaffinic hydrocarbons, naphtha or kerosene, which may be 
dissolved in a suitable solvent and fogged or sprayed without water. 
Usually it is desirable to incorporate emulsifying agents and other 
wetting agents to insure complete contact with the fungus.

The following are examples of preparation of representative compounds of 
the invention, and are presented by way of illustration, and are not 
intended to be limiting unless otherwise specified. 
EXAMPLE 1 
N-(3-Chloro-2,6-Dinitro-4-Trifluoromethylphenyl)-Pyrrolidone 
Sodium methoxide (5.4 g., 0.1 mole) in 200 ml. of benzene is charged into a 
500 cc 4-neck flask maintained under an atmosphere of nitrogen, and heated 
to 70.degree. C. Pyrrolidinone (10.2 g., 0.12 mole) then is added during a 
period of 1 hour while maintaining the reactants at 70.degree.-80.degree. 
C. At the conclusion of the reaction period, 35 cc. of a benzene-methanol 
mixture is distilled off. 100 cc. of dimethylformamide and benzene is 
removed under vaccuum until the pot temperature reaches 80.degree. C. 
2,4-Dichloro-35-dinitrobenzotrifluoride (30.5 g., 0.1 mole) in 20 cc. of 
dimethylformamide is added to the residual material, namely, sodium salt 
of pyrrolidone, at room temperature. The mixture is stirred for 19 hours 
at room temperature, and then is heated at 75.degree. C for 2 hours. The 
dimethylformamide solvent then is removed at 80.degree. C under 1 mm. 
pressure. The residue is partitioned between toluene and water; the 
water-washed toluene layer separated, the toluene removed by 
rotoevaporation, and the product is crystallized twice from methanol. The 
yield is 3.5 g. (9%), m.p. 121.degree.-122.degree. C. Anal. Calcd for 
Nitrogen: N,11.87; Found: 11.67, Calcd for Chlorine, 10.0; Found: 9.80. 
EXAMPLE 2 
N-(3-Halo-2,6-Dinitro-4-Trifluoromethylphenyl)-Thiopyrrolidone 
The procedure of Example 1 is followed except that thiopyrrolidone 
(prepared as described in the literature* by reaction of pyrrolidone and 
phosphorous pentasulfide in refluxing benzene) is used in place of 
pyrrolidone, to provide the desired compound. 
FNT * Tafel et al., Ber. 40, 2842-48 (1907) 
EXAMPLE 3 
N-(3-Halo-2,6-Dinitro-4-trifluoromethylphenyl)-3-Butyl-Pyrrolidone 
The procedure of Example 1 is followed except that 3-butylpyrrolidone 
(prepared as described in the literature* by reaction of pyrrolidone with 
1-benzene in isopropanol with di-butyl peroxide as a catalyst at 
35.degree. C for 16 hours) is used in place of pyrrolidone, to provide the 
desired product. 
FNT * D. Elad and J. Sinnreich, Chemical Industry (London) 1965 (18), P. 768-9; 
2) Nikishin, G. I. and Mustafaer, R. I., Chemical Abstracts 62, 2753 h 
(1965). 
EXAMPLE 4 
Foliar Fungicidal Tests 
The product of Example 1 was tested on tomato early blight as follows: 
Young tomato seedlings 4 to 5 weeks of age were atomized while rotating on 
a turntable with a suspension of the test material diluted to 250 ppm. 
After the deposit dried, the plants were atomized with a spore suspension 
and incubated in a humidity cabinet at 70.degree. to 75.degree. F for 24 
hours. Then they are held in a greenhouse until lesions appear (usually 2 
to 3 days). The severity of infection is rated on a scale of 0 (no 
reduction) to 10 (complete elimination of infection). The results versus 
the standard Maneb, managanese ethyl bis-dithicarbamate, are as follows: 
______________________________________ 
Fungitoxicity Rating 
Conc., ppm. Compound of Ex. 1 Maneb 
______________________________________ 
250 8.0 9.5 
______________________________________ 
EXAMPLE 5 
The product of Example 1 was tested on rice leaf spot as follows: Young 
Star Bonnet rice plants about 2 weeks old growing in 2.5 inch pot were 
sprayed while rotating with a suspension containing 250 ppm. of material. 
After the spray deposit dried, the plants were atomixed with a conidial 
suspension and placed in a moist chamber at 75.degree. F. for 24 hours to 
facilitate infection. After discrete lesions appeared in the unprotected 
controls (2 days), the infection was rated versus the commercial standard 
Maneb. 
______________________________________ 
Fungitoxicity Rating 
Conc., ppm Compound of Ex. 1 Maneb 
______________________________________ 
250 8.0 9.5 
______________________________________ 
While the invention has been described with particular reference to certain 
embodiments thereof, it will be understood that certain modifications and 
changes may be made which are within the skill of the art. Therefore it is 
intended to be bound only by the appended claims.