Heterocyclic compounds

Abstract

A compound of the formula ##STR1## wherein typical representations of X, Y and Z is oxygen or sulfur; R.sub.1 is methyl; R.sub.2 is phenyl substituted with chlor, methyl, methoxy, nitro or methylenedioxy; and R.sub.3 is cyclohexyl, methylcyclohexyl or tetrahydropyranyl, is useful as an acaricide.

Description

The present invention relates to a novel heterocyclic compound, acaricidal compositions in the form of mixtures of such compounds with carrier vehicles, and methods for producing such compounds and for using such compounds for controlling acarids.

Some derivatives having oxazolidone or thiazolidone skeletons are known as herbicides or anticonvulsants, and there are descriptions, for instance, in U.S. Pat. No. 3,247,219 and JACS 73,95 (1951) on 3-carbamoyloxazolidone derivatives, and in U.S. Pat. No. 3,491,108 on thiazolidone derivatives.

The present invention provides a compound having the formula ##STR2## wherein X, Y and Z is oxygen or sulfur; R.sub.1 is alkyl of one to four carbon atoms; R.sub.2 is five membered heterocycle having oxygen or sulfur, phenyl, substituted phenyl having one or two substituent alkyl, halogen, haloalkyl, alkoxy, nitro or methylenedioxy; and R.sub.3 is five to seven membered cycloalkyl, cycloalkenyl, or heterocycle having oxygen, sulfur, or nitrogen, being in each case with or without substituent.

The compounds of the formula (I) exhibit strong acaricidal properties.

The present invention further provides processes for the production of the compound of the formula (I) the process being described as follows:

(a) The compound of the formula ##STR3## wherein R.sub.1, R.sub.2, X and Y have the above meanings, is reacted with the isocyanate or isothiocyanate of the formula

R.sub.3 NCZ (III) wherein R.sub.3 and Z have the above meanings.

The starting material indicated by the formula (II) can be prepared, for example, as illustrated by the following equations: ##STR4##

The compound of the formula (II) is dissolved in an inert organic solvent such as toluene, tetrahydrofuran and dimethylsulfoxide, and to the solution are added the compound of the formula (III) and a catalyst, for instance, such a basic compound as 1,8-diazabicyclo (5, 4, 0) undecene-7 (DBU), sodium hydride and tertiary amines, or a Lewis acid such as stannous chloride, boron trifluoride and zinc chloride. The reaction is usually carried out at 0.degree. C. to room temperature under stirring for a period of one to several hours. After the reaction is completed, the reaction mixture is poured into water, and the product is separated by filtration or solvent extraction.

(b) The compound of the formula ##STR5## wherein R.sub.1, R.sub.2, R.sub.3, X and Z have the above meanings, is reacted with a carbonylating or thiocarbonylating reagent in the presence of an acid-binding reagent. The starting material indicated by the formula (V) can be prepared, for example, by reacting the compound represented by the formula (III) with the compound represented by the formula (IV). As the carbonylating or thiocarbonylating reagent, such conventional reagents as potassium carbonate, phosgene, thiophosgene, trichloromethyl chloroformate are suitable. For the acid-binding reagent, amines such as dimethylamiline or triethylamine and other basic compoounds are employed. The compound of the formula (V) and the acid-binding reagent are dissolved in an inert organic solvent such as benzene, chloroform and ethylacetate, and to the solution is added the carbonylating or thiocarbonylating reagent. The reaction is usually conducted at 0.degree. C. to room temperature for a period of one to several hours. After the reaction is completed, the basic material in the reaction mixture is removed by washing the mixture with dilute hydrochloric acid or water, and thereafter it is worked up to obtain the product in accordance with usual procedures.

In the novel compounds of the invention, two substituents R.sub.1 and R.sub.2 on the heterocyclic ring are trans disposition, as shown in the formula (I). In case R.sub.3 is a certain substituted cyclohexyl or tetrahydropyranyl ring, other isomer configurations present in the carbamoyl moiety, however, all the isomers thus formed are also within the scope of this invention.

The manner in which the compound of the present invention can be prepared is illustrated, without limitation, by the following examples.

EXAMPLE 1

Trans-3-cyclohexylcarbamoyl-4-methyl-5-(4-methylphenyl)-2-oxazolidone

Into 30 ml of dimethylsulfoxide was dissolved 3.8 g of trans-4-methyl-5-(4-methylphenyl)-2-oxazolidone, and to the solution were added with ice-cooling 2.7 g of cyclohexylisocyanate and one drop of DBU. The mixture was warmed gradually to room temperature with stirring, and the reaction was continued for 1 hour. The reaction mixture was poured into water, and extracted with ethylacetate. The ethylacetate layer was dried, the solvent was evaporated and the residue was recrystallized from ligroin. The yield of the desired product was 4.7 g.

EXAMPLE 2

Trans-4-methyl-5-(4-methylphenyl)-3-(2-tetrahydropyranylcarbamoyl)-2-oxazolidone

Into 20 ml of dimethylsulfoxide was dissolved 1.5 g of trans-4-methyl-5-(4-methylphenyl)-2-oxazolidone, and to the solution were added with ice-cooling 0.9 g of 2-tetrahydropyranyl isocyanate and one drop of DBU. The mixture was stirred for one hour at room temperature. The reaction mixture was poured into water, and extracted with ethylacetate. The ethylacetate layer was dried, the solvent was evaporated and the oily residue was purified with a column chromatography. The yield of the desired product was 0.7 g.

EXAMPLE 3

Trans-3-cyclohexylcarbamoyl-4-methyl-5-(2-thienyl)-2-oxazolidone

Into 10 ml of dimethylsulfoxide were dissolved 2 g of trans-4-methyl-5-thienyl-2-oxazolidone and 1.4 g of cyclohexylisocyanate, and then 1 g of DBU was added to the solution at room temperature. After the mixture was stirred for two hours, the reaction mixture was poured into ice-cold water, the deposited crystals were filtered and dried. The yield of the desired product, was 2.8 g.

EXAMPLE 4

Trans-3-cyclohexylcarbamoyl-4-methyl-5-(4-methylphenyl)-2-oxazolidone

Into 100 ml of ethylacetate were dissolved in 2 g of 1-cyclohexyl-3-[1-hydroxy-1-(4-methylphenyl)-2-propyl] urea and 1.6 g of N, N-dimethylaniline, and to the solution was added with stirring at 5.degree. C. to 10.degree. C. 1 g of trichloromethylchloroformate dissolved in 10 ml of ethylacetate. After the mixture was stirred for one hour at the temperature, the reaction mixture was washed with a 5% hydrochloric acid and water, the washed mixture was dried and the solvent was evaporated. The yield of the desired product was 1.7 g.

EXAMPLE 5

Trans-4-methyl-5-(4-methylphenyl)-3-(2-tetrahydropyranylcarbamoyl)oxazolidine-2-thione

Into 10 ml of ethylacetate were dissolved 1.2 g of 1-(2-tetrahydropyranyl)-3-[threo-2-hydroxy-1-(4-methylphenyl)-2-propyl] urea and 1.0 g of N,N-dimethylaniline, and to the solution was added with stirring at 0.degree. C. 0.7 g of thiophosgene dissolved in 5 ml of ethylacetate. After the mixture was stirred for 3 hours at 0.degree. C., the reaction mixture was poured into a 5% hydrochloric acid, and extracted with ethylacetate. The ethylacetate layer was dried, the solvent was evaporated and the oily residue was purified with a column chromatography. The yield of the desired product was 0.5 g.

EXAMPLE 6

Trans-4-methyl-5-(4-methylphenyl)-3-cyclohexylcarbamoyl-2-thiazolidone

Into 50 ml of ethylacetate were dissolved 4.8 g of 1-cyclohexyl-3-[threo-1-mercapto-1-(4-methylphenyl)-2-propyl] urea and 3.8 g of N, N-dimethylaniline, and to the solution was added with stirring 2.5 g of trichloromethyl chloroformate dissolved in 10 ml of ethylacetate. After the mixture was stirred for four hours at room temperature, the reaction mixture was washed with a 5% hydrochloric acid and water, the washed mixture was dried and the solvent was evaporated. The oily residue was purified with a column chromatography. The yield of the desired product was 3.4 g.

EXAMPLE 7

Trans-4-methyl-5-(4-chlorophenyl)-3-cyclohexylcarbamoyl-2-thiazolidone

Into 10 ml of dimethylsulfoxide were dissolved 2 g of trans-4-methyl-5-(4-chlorophenyl)-2-thiazolidone and several drops of DBU, and to the solution was added dropwise 1.2 g of cyclohexyl isocyanate with cooling. After the mixture was stirred for 3 hours at room temperature, the reaction mixture was poured into ice-water and extracted with chloroform. The chloroform layer was washed with water, dried, and the solvend was evaporated. The oily residue was purified with a column chromatography. The yield of the desired product was 2.6 g.

EXAMPLE 8

Trans-4-methyl-5-(4-methylphenyl)-3-(trans-2-methylcyclohexylcarbamoyl)-2-thiazolidone

Into 60 ml of benzene was dissolved 3 g of trans-4-methyl-5-(4-methylphenyl)-2-nitrosoamino-2-thiazoline, and to the solution were added at room temperature 2 g of trans-2-methylcyclohexyl isocyanate and several drops of triethylamine. After the mixture was stirred for one hour at room temperature, the reaction was continued for further 3 hours under heating and reflux. The reaction mixture was washed with water, dried and the solvent was evaporated. The oily residue was purified with a column chromatography. The yield of the desired product was 1.8 g.

Inclusive of the above, compounds within the scope of this invention which can be prepared in an analogeous manner are tabulated in Table I.

TABLE 1__________________________________________________________________________ Compound ##STR6## PropertiesPhysicalNo. X Y Z R.sub.1 R.sub.2 R.sub.3 [m.p.] .degree.C.__________________________________________________________________________1 O O O CH.sub.3 ##STR7## ##STR8## [98-100]2 " " " " ##STR9## " n.sub.D.sup.29 1.53303 " " " " ##STR10## " [64-65]4 " " " " ##STR11## " [85-86.5]5 " " " " ##STR12## " [129-130]6 " " " " ##STR13## " [105-107]7 " " " " ##STR14## " [80-82]8 " " " " ##STR15## " [126-128]9 " " " C.sub.2 H.sub.5 ##STR16## " n.sub.D.sup.30.5 1.526810 " " " CH.sub.3 ##STR17## " [ 66-68] Racemate11 " " " " ##STR18## " [70-72]12 " " S " ##STR19## " [115-116]13 " " O " ##STR20## " [105-107]14 " " " " ##STR21## " [76-78]15 " " " " ##STR22## " [76-78]16 " " " " ##STR23## ##STR24## [94.5-96]17 " " " " ##STR25## ##STR26## [160-162]18 " " " " ##STR27## ##STR28## [71-72]19 " " " " " ##STR29## [61-62]20 " S " " ##STR30## ##STR31## [87-89]21 " O " " ##STR32## " [50-52]22 " " " " ##STR33## " [127-128.5]23 " " " " ##STR34## " [152-154]24 " " " " ##STR35## " [74-76]25 " S " " ##STR36## " n.sub.D.sup.28 1.573926 " O " " ##STR37## " n.sub.D.sup.26 1.533927 " " " " ##STR38## " [89-90.5]28 " " " " ##STR39## " [78.5-80]29 " " " " ##STR40## " [45-47]30 " " " " ##STR41## ##STR42## n.sub.D.sup.27 1.5331 (N/CH.sub.3 Cis:trans = 60:40)*31 " " " " ##STR43## ##STR44## [51-59] (N/CH.sub.3 :trans)32 " " " " " ##STR45## [109-120] (N/CH.sub.3 :cis)33 " " " " " ##STR46## n.sub.D.sup.20 1.5361 (N/CH.sub.3 :cis/trans = 7/3)34 " " " " " ##STR47## [112-118] (N/CH.sub.3 = trans)35 " " " " " ##STR48## [116-122]36 " " " " " ##STR49## [95-96]37 " " " " ##STR50## ##STR51## [127-129]38 S S " " ##STR52## ##STR53## [96-97]39 O O S " ##STR54## " [93-95]40 S " O " ##STR55## " [86-87]41 O S " " " ##STR56## n.sub.D.sup.20.5 1.580042 " " " " ##STR57## ##STR58## [89-91]43 " O S " ##STR59## " [90-92]44 " " O " ##STR60## ##STR61## [88-90]45 " " " " ##STR62## " [75-76]46 " " " " ##STR63## ##STR64## [109-111]47 " " " " ##STR65## ##STR66## n.sub.D.sup.17.2 1.5460 (N/CH.sub.3 :trans)48 " " " " ##STR67## ##STR68## n.sub.D.sup.17.8 1.537649 " " " " ##STR69## ##STR70## n.sub.D.sup.19.3 1.539550 " " " " ##STR71## ##STR72## [95-97]51 " " " " " ##STR73## [85-104]52 " " " " " ##STR74## [78-80]53 " " " " " ##STR75## n.sub.D.sup.20.5 1.560354 " " " " ##STR76## ##STR77## [122-123]55 S " " " ##STR78## " [93-96]56 " " " " ##STR79## ##STR80## [86.5-98] (N/CH.sub.3 :trans)57 " " " " " ##STR81## n.sub.D.sup.27 1.563858 " " " " ##STR82## ##STR83## [93-96]59 " " " " ##STR84## " [ 84-85]60 " " " " ##STR85## ##STR86## [147-149] (N/CH.sub.3 :trans)61 " " " " " ##STR87## [96-101]62 " " " " ##STR88## ##STR89## [125-128]63 " " " " ##STR90## ##STR91## [76-77]64 " " " " " ##STR92## n.sub.D.sup.26.5 1.557765 " " " " " ##STR93## [ 72.5-74.5] (N/CH.sub.3 :cis)66 " " S " " ##STR94## [94.5-97]67 " " O " " ##STR95## n.sub.D.sup.28.0 1.553268 " " " " ##STR96## ##STR97## n.sub.D.sup.30.0 1.565769 " " " " ##STR98## " [116-117.5]70 " " " " ##STR99## " [85.5-88]71 " " " " ##STR100## " [46-49]72 " " " " ##STR101## " [99-102.5]73 " " " " ##STR102## " [77-79]74 " " " " ##STR103## " [97-99]75 " " " " ##STR104## " [136-138]76 " " " " ##STR105## " [99-101]77 " " " " ##STR106## " [90-91.5]78 " " " " ##STR107## " n.sub.D.sup.30.5 1.559079 " " " " ##STR108## " n.sub.D.sup.26 1.575180 " " S " ##STR109## " [108-110]81 " " O " " ##STR110## [116-121.5] (N/CH.sub.3 :trans)82 " " " " " ##STR111## [83-87] (N/CH.sub.3 :cis)83 " " " " " ##STR112## [149-153] (N/CH.sub.3 :trans)84 " " " " " ##STR113## n.sub.D.sup.29 1.580185 " " " " " ##STR114## n.sub.D.sup.29 1.5760 (Isomer)86 " " " " " ##STR115## n.sub.D.sup.28.5 1.560487 " " " " ##STR116## ##STR117## [106-108]88 " " " " ##STR118## ##STR119## [97-98]89 " " " " " ##STR120## [87-89]90 " " " " ##STR121## ##STR122## [120-121]91 " " " " ##STR123## " [95-91]92 " " " C.sub.2 H.sub.5 ##STR124## " [113-115]93 " " " CH.sub.3 ##STR125## " [120-123]94 " " " " ##STR126## ##STR127## [83-85]95 " " " " ##STR128## ##STR129## n.sub.D.sup.27.5 1.567996 " " " " ##STR130## " n.sub.D.sup.25.5 1.580397 " " " " ##STR131## ##STR132## [67-68]98 " " " " ##STR133## ##STR134## [133-137]99 " " " " ##STR135## " [133-135]100 " " " " ##STR136## " [117-119]101 " " " " ##STR137## " [118.5-121.5]102 " " " .sup.i C.sub.3 H.sub.7 ##STR138## " n.sub.D.sup.30 1.5886103 " S " CH.sub.3 ##STR139## " [101-103]104 " O " " ##STR140## " [114-117]105 O " " " ##STR141## " [76-78]106 " " " " ##STR142## ##STR143## [126-128]107 " " " " ##STR144## " [66-68]108 " " " " ##STR145## " [109-111]__________________________________________________________________________ *Isomer configuration in carbamoyl moiety

As already mentioned, the compounds of this invention exhibit outstanding acaricidal properties, and they are especially useful for controlling eggs and larvae of acarids. Among the acarids which can be effectively controlled with the compounds are the two spotted spider mite, citrus red mite, and the like. The compounds may be used with success for the control of ticks. Furthermore, herbicidal usages are expected for a certain group of the compounds.

The compounds according to this invention are utilized, if desired, in a form of the usual acaricidal formulations with conventional diluents or extenders, and the formulations include wettable powders, granules, dusts, emulsifiable concentrates, flowable formulations, and the like. As solid carrier vehicles, such cereal flours as soy bean flour and wheat flour, such ground minerals as diatomaceous earth, apetite, gypsum, talc, pyrophyllite and clay are used. As liquid diluent carriers such inert organic liquids as kerosene, mineral oil, petrolum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, alcohol, and acetone, as well as water are employed. Conventional pesticidal surface-active agents including emulsifying agents and/or dispersing agents may be used when homogeneous and stable formulations are desired.

The concentration of the active ingredient in the acaricidal compositions may vary in accordance with types of the formulation, and it is settled generally at about 5 to 80 weight percent and preferably 20 to 80 weight percent for the wettable powders; 5 to 70 weight percent and preferably 10 to 50 weight percent for the emulsifiable concentrates; and 0.5 to 20 weight percent and preferably 1 to 10 weight percent for the dust formulation.

Wettable powders, emulsifiable concentrates and flowable formulations thus formulated are usually diluted with water to form the suspensions or emulsions, which are applied by spraying or drenching. Dusts and granules are applied directly.

Non-limiting examples of the acaricidal composition of the invention are as mentioned below:

EXAMPLE 9

Emulsifiable Concentrate

______________________________________Compound of this invention 10 parts by weightDimethylformamide 50 parts by weightXylene 35 parts by weightAlkylarylpolyoxyethylene ether 5 parts by weight______________________________________

These are mixed together to provide an emulsifiable concentrate. It is diluted with water to an emulsion of the desired concentration.

EXAMPLE 10

Wettable Powder

______________________________________Compound of this invention 20 parts by weightDiatomaceous earth 70 parts by weightWhite carbon 5 parts by weightSodium alkylsulfate 5 parts by weight______________________________________

These are mixed and ground to provide homogeneous powders. It is diluted with water to a suspension of the desired concentration.

EXAMPLE 11

Dust Formulation

______________________________________Compound of this invention 1 parts by weightTalc 98.6 parts by weightSilicone Oil 0.3 parts by weightAlkylarylpolyxyethylene ether 0.1 parts by weight______________________________________

These are mixed and pulverized to provide homogeneous fine powders.

Use of the combinations of the compound of the present invention with other plant protection agents such as other acaricides, insecticides or herbicides may provide acaricidal and insecticidal compositions which achieve results unattainable with separate compositions of the individual component. Other components with which the compound of the present invention can be used are, for example, as follows:

Acaricides

chlorfenethol, chlorobenzilate, chloropropylate, proclonol, phenisobromolate, dicorol, dinobuton, binapacryl, chlordimeform, amitraz, propargite, PPPS, benzoxamate, cyhexatin, fenlutatin oxide, polynactins, chinomethionate, thioquinox, chlorfenson, tetradifon, tetrasul, cycloprate, Kayacide, Kayahope, 3-n-dodecyl-1,4-naphthoquinone-2-yl acetate, Calcium polysulfide

Insecticides

(Organophosphorous compounds)

fenthion, fenitrothion, diazinon, chlorpyrifos, EPS, vamidothion, phenthoate, dimethoate, formothion, malathion, trichlorfon thiometon, phosmet, menazon, dichlorvos, acephate, EPBP, dialifor, methyl parathion, oxydemeton methyl, ethion, aldicarb, propoxur

(Pyrethroids)

permethrin, cypermethrin, decamethrin, fenvalerate, fenpropathrin, pyrethrins, allethrins, tetramethrin, resmethrin, barthrin, dimethrin, propathrin, prothrin, 3-phenoxybenzyl-2,2-dichloro-1-(4-ethoxyphenyl)-1-cyclopropancarboxylate, .alpha.-cyano-3-phenoxybenzyl-2,2-dichloro-1-(4-ethoxyphenyl)-1-cyclopropanecarboxylate, (RS)-.alpha.-cyano-3-phenoxybenzyl(RS)-2-(4-trichloromethoxyphenyl)-3-methylbutylate, (RS)-.alpha.-cyano-3-phenoxybenzyl(RS)-2-(2-chloro-4-trichloromethylanilino)-3-methylbutylate.

The unexpected superiority and outstanding activity of the novel compounds of the present invention is illustrated, without limitation, by the following test:

Test 1

The primary leaves of kidney beans planted in pots were infested respectively with 30 adult females of the two-spotted spider mite. The leaves were sprayed until dew moist with an aqueous emulsion prepared with the emulsion concentrate of Example 9 and containing 500 ppm or 125 ppm of the active compound. After 3 days of the ovipositing period, mites which survived as well as killed were removed from the leaves. On the 11th day, the degree of destruction as a percentage of (A-B)/A wherein A means the number of mites developed from eggs on untreated leaves and B means the number of mites developed from eggs on treated leaves. The result are as shown in the following Table 2.

TABLE 2______________________________________ Degree of DestructionCompound No. 500 ppm (%) 125 ppm (%)______________________________________1 100 1002 100 994 100 1005 100 978 100 959 95 8410 100 10011 100 8512 98 9814 100 9516 100 10019 100 10021 100 10023 100 6424 100 10025 100 10026 100 8627 100 9928 99 8829 100 9930 100 10031 100 10033 100 8534 100 10036 100 9537 100 10038 100 10040 100 10041 100 10042 100 10043 100 7744 100 10045 100 10047 100 10048 100 10049 100 10050 90 6055 100 10056 100 10057 100 10058 100 10059 100 10060 100 10061 100 10063 100 10064 100 9865 100 10066 100 10067 100 10068 100 10069 100 10070 100 10071 100 10073 100 10074 100 8075 100 6276 100 10077 100 10078 100 10079 100 10080 100 9981 100 10082 100 10083 100 10084 100 10085 100 9886 100 10088 100 9089 100 10090 100 9191 100 10092 100 10093 95 6394 100 9297 100 10098 100 10099 100 100101 100 100103 100 100104 100 100*chlordimeform 100 55______________________________________ ##STR146##

Claims

1. A compound represented by the formula ##STR147## or racemate thereof wherein each of Y and Z is oxygen or sulfur,

R.sub.1 is alkyl of one to four carbon atoms,

R.sub.2 is thienyl, furyl, phenyl, phenyl having one alkoxy, or phenyl having one or two substituents selected from a group consisting of alkyl, halogen, haloalkyl, nitro and methylenedioxy, and

R.sub.3 is a five to seven membered cycloalkyl with or without one or two methyl, cyclohexenyl or tetrahydropyranyl.

2. A compound according to claim 1 wherein R.sub.1 is methyl; R.sub.2 is phenyl substituted with chlor, methyl, methoxy or methylenedioxy; and R.sub.3 is cyclohexyl, methylcyclohexyl or tetrahydropyranyl.

3. A compound according to claim 2 wherein Y and Z are oxygen.

4. Trans-4-methyl-5-[4-chlorophenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

5. Trans-4-methyl-5-[4-bromophenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

6. Trans-4-methyl-5-[4-trifluoromethylphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

7. Trans-4-methyl-5-[4-chlorophenyl]-3-[2-tetrahydropyranylcarbamoyl]-2-thiazolidone of claim 1.

8. Trans-4-methyl-5-[4-methylphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

9. Trans-4-methyl-5-phenyl-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

10. Trans-4-methyl-5-[4-methylphenyl]-3-[2-methylcyclohexylcarbamoyl]-2-thiazolidone of claim 1.

11. Trans-4-methyl-5-[4-methylphenyl]-3-[2-tetrahydropyranylcarbamoyl]-2-thiazolidone of claim 1.

12. Trans-4-methyl-5-[4-methylphenyl]-3-[4-methylcyclohexylcarbamoyl]-2-thiazolidone of claim 1.

13. Trans-4-methyl-5-[4-fluorophenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

14. Trans-4-methyl-5-[4-chlorophenyl]-3-[2-methylcyclohexylcarbamoyl]-2-thiazolidone of claim 1.

15. Trans-4-methyl-5-[4-chlorophenyl]-3-[4-methylcyclohexylcarbamoyl]-2-thiazolidone of claim 1.

16. Trans-4-methyl-5-[3,4-dimethylphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

17. Trans-4-methyl-5-[4-methylphenyl]-3-cycloheptylcarbamoyl-2-thiazolidone of claim 1.

18. Trans-4-methyl-5-[4-methylphenyl]-3-cyclohexylthiocarbamoyl-2-thiazolidone of claim 1.

19. Trans-4-methyl-5-[3-methylphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

20. Trans-4-methyl-5-[2-methylphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

21. Trans-4-methyl-5-[3-chlorophenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

22. Trans-4-methyl-5-[3,4-methylenedioxyphenyl]-3-cyclohexylcarbamoyl-2-thiazolidone of claim 1.

23. Trans-4-methyl-5-[4-chlorophenyl]-3-cycloheptylcarbamoyl-2-thiazolidone of claim 1.

24. Trans-4-methyl-5-[4-chlorophenyl]-3-cyclohexylcarbamoylthiazolidine-2-thione of claim 1.

25. An acaricidal composition comprising an inert carrier and an effective amount of a compound of claim 1.

26. An acaricidal composition comprising an inert carrier and an effective amount of a compound of claim 2.

27. An acaricidal composition comprising an inert carrier and an effective amount of a compound of claim 3.