GB2184120A - Novel azlactone derivatives, process for the preparation thereof and pesticides containing these compounds as active ingredient - Google Patents

Abstract

Compounds of Formula (I> <IMAGE> wherein W, X and Z stand for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; V stands for hydrogen. chlorine or nitro; R1 stands for hydrogen or nitro and R2 represents C1-4 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W a) only one can stand for trifluoromethyl; and b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and c) not more than four can stand for hydrogen. The compounds exhibit herbicidal and/or fungicidal properties.

Description

SPECIFICATION Novel azlactone derivatives, process for the preparation thereof and pesticides containing these compounds as active ingredient This invention relates to new unsaturated azlactone derivatives, a process for the preparation thereof and pesticidal compositions comprising the same.

According to an aspect of the present invention there are provided new unsaturated azlactone derivatives of the general Formula (I)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl; R1 stands for hydrogen or nitro and R2 represents C14 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stand for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogen.

The new compounds of the present invention possess pesticidal-particularly herbicidal and/or fungicidal-properties.

The new pesticidal compounds of the general Formula (I) are unsaturated azlactone derivatives.

The first unsaturated azlactone was prepared by Plöchl in 1883 by the reaction of benzaldehyde and hyppuric acid in acetic anhydride [P16chl: Ber. 16, 2815 (1883)]. The exact structure of the compounds was determined by Erlenmeyer [Ann. 275, 1 (1893); Ber. 33, 2036 (1900)] and the reaction was extended to other aldehydes, too [Ann., 307, 138 (1899); 316, 145 (1901); 337, 271, 283, 294 (1904); Ber., 30, 2981 (1897); Ber., 35, 384 (1902)].

A general review of the preparation of azlactones is presented by H. E. Carter [Organic Reactions Vol. 3., page 198, John Wiley London (1949)].

According to a further aspect of the present invention there is provided a process for the preparation of new compounds of the general Formula (I),

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl; R1 stands for hydrogen or nitro and R2 represents C14 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stand for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogen which comprises reacting a compound of the general Formula (II)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl and R, stands for hydrogen or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stant for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogenwith a N-acyl-glycine of the general Formula (III)

(wherein Ac stands for C24 acyl, benzoyl, chlorobenzoyl or nitrobenzoyl) in the presence of an acetate preferably anhydrous sodium acetate-and a carboxylic acid anhydride-preferably acetic anhydride at a temperature between 40"C and the boiling point of the reaction mixture, whereby the N-acyl-glycine of the general Formula (III) is used in a molar excess of 0-1 mole.

The starting materials of the general Formula (II) are partly known phenoxybenzaldehyde derivatives (USP 4,306,900; DE-OS 3017795). The new compounds of the general Formula (II) are disclosed in our unpublished patent application (Hungarian patent application Ser. No.

158/84; Hungarian priority: 16th January 1984).

The starting materials of the general Formula (III) are known compounds.

Several further new compounds were prepared from substituted 3-phenoxy-benzaldehydes and substituted 5-phenoxy-2-nitro-benzaldehydes. Thus e.g. substituted phenoxy benzaldehyde acetales (EP 0 064 658) and diacetates (DE-OS 3 044 810), substituted phenoxy cinnamic acid derivatives (EP 0053321), substituted phenoxy oximes, -carboximes (DE-OS 3 017 795) were produced. According to the said references all the compounds exhibit herbicidal effect.

It has been found in the course of our experiments that N-acyl-glycines can be readily condensed with substituted 3-phenoxy-benzaldehydes and substituted 5-phenoxy-2-nitro-benzaldehydes, respectively, and the new compounds of the general Formula (I) thus obtained possess very favourable herbicidal and/or fungicidal effect.

The following compounds of the general Formula (I) exhibit particularly good herbicidal and/or fungicidal effect: 4-{3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzylidenej-2-methyl-oxazoline-5-one; 4-{3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzylidenej-2-phenyl-oxazoline-5-one; 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5-one; 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5-one; 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-phenyl-oxazoline-5-one.

Particularly preferred representatives of the compounds of the general Formula (I) are the following derivatives: 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-ethyl-oxazoline-5-one; 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-phenyl-oxazoline-5-one.

According to the present invention the new compounds of the general Formula (I) are prepared by methods known per se, e.g.: (a) According to a form of realization of the process of the present invention a phenoxy benzaldehyde derivative of the general Formula (II) is reacted with a compound of the general Formula (IV)

(wherein R2 is as stated above) in the presence of a carboxylic acid anhydride, preferably acetic anhydride.

The compounds of the general Formula (IV) are, however, unstable and can only be isolated with difficulties. For this reason it is preferred to prepare the said componds from N-acyl-glycine derivatives of the general Formula (III) (wherein Ac is as stated above) in the presence of perchloric acid and a carboxylic acid anhydride-preferably acetic anhydride. Thus dehydration takes place. The perchlorate salt thus formed is stable and can be deprotonised under mild conditions by treatment with a base e.g. with triethyl amine [Comprehensive Heterocyclic Chemistry (Ed. Kevint T. Potts), Pergamen Press, Oxford, New York-Toronto-Sidney-Paris- Frankfurt, Vol. 6., Chap. 4.18.4.3.4. (1984)].

(b) According to a further form of realization of the process of the present invention the compounds of the general Formula (I) are prepared by reacting a substituted phenoxy benzaldehyde of the general Formula (II) with N-acyl-glycine of the general Formula (III) in the presence of a carboxylic acid anhydride and if desired an acetate salt at a temperature between 40"C and the boiling point of the reaction mixture.

As acetate salt any suitable acetate comprising an inorganic cation can be used, e.g. copper or lead acetate. Preferably anhydrous sodium acetate is used.

A carboxylic acid anhydride one may preferably use acetic anhydride but the condensation reaction can be readily performed in the presence of an other carboxylic acid anhydride, too.

Thus for this purpose e.g. propionic anhydride, butyric anhydride etc. may also be used.

The reaction time may vary between 10 minutes and 10 hours. If acetyl glycine is used as compound of the general Formula (III), the reaction time is generally longer than in the case of the reaction carried out with hyppuric acid.

The reaction may be accomplished at a temperature between 40"C and 160"C. When carrying out the reaction for the same period of time the use of N-acetyl-glycine requires a higher temperature than hyppuric acid. Generally good yields can be achieved when carrying out the reactionat 90-110"C for 1-3 hours.

The condensation reaction can be carried out by admixing the compounds of the general Formula (II) and (III) in a vessel or by introducing the reaction components in any order of succession.

One may also proceed by preparing the N-acyl-glycine of the general Formula (III) "in situ" in the reaction mixture by reacting glycine with a suitable acylating agent (e.g. carboxylic acid anhydride; acid chloride, ester etc).

The starting materials of the general Formula (Il) and (Ill) may be generally used in an equimolar amount but one may also preferably proceed by using one of the said starting materials-generally the N-acyl-glycine of the general Formula (Ill)--in an excess.

The new compounds of the general Formula (I) can be isolated from the reaction mixture by known methods (e.g. by filtration after cooling). On pouring the reaction mixture into ice-water the acetic anhydride is hydrolysed and the product may be isolated by filtration. Water may be replaced by methanol, ethanol, isopropanol etc. The product can be purified by crystallization from a suitable solvent (e.g. methanol, ethanol, isopropanol, benzene, petrolether, ethyl acetate etc.) The phenoxy-benzaldehyde derivatives of the general Formula (II) are-as already mentioned above-partly new compounds. The said new compounds are claimed in our pending Hungarian Application 158/84 (British Application 8501038-2,154,235 A). These compounds can be prepared by known methods, e.g. as follows: (a) According to the classical Ullmann-type ether synthesis, the alkali metal salt of the corresponding phenol derivative is reacted in the presence of a copper catalyst or in the absence of any catalyst with the corresponding halogenated benzene derivative. The reaction of the alkali salt of a trifluoromethyl phenol derivative and a 3-halogeno-benzaldehyde or 2-nitro-5-halogenobenzaldehyde can instead be carried out by reacting an alkali salt of 3-hydroxy-benzaldehyde or m-cresol with the corresponding substituted benzotrifluoride derivative; if m-cresol is used the aldehyde derivatie may be obtained by hydrolysing the benzal halide; the said benzal halide can be prepared by radical-type halogenation of a toluene derivative.The aldehydes can furtheron be prepared by partial reduction of a carboxylic acid or carboxylic acid ester or partial oxidation of an aminomethyl, chloromethyl or hydroxymethyl derivative.

According to a further method the formyl group can be formed by subjecting an imine obtained by partial reduction of a nitrile to hydrolysis.

(b)- Shorter reaction time and higher yield can be achieved by using a dipolar aprotic solvent (e.g. dimethyl formamide, dimethyl acetamide, sulfolane, dimethyl sulfoxide, acetone etc). In this case if a solvent having a suitable boiling point is used, the reaction may also be performed in the absence of a catalyst.

(c) In a 5N2 type ether-forming reaction an anion of a phenolate is reacted with a neutral molecule (halogenated benzene). When judging the role of the introduced nucleophilic group, the nucleophilic capacity and sterical factors are to be taken into consideration. The character of the group to be replaced (generally halogen) and the activating effect of the substituents of the aromatic ring have also an important role in the determination of the reaction velocity.

The substituted phenoxy-2-nitro-benza Idehydes may be prepared by various advantageous methods e.g. as follows: -the substituted halogeno benzotrifluoride is directly coupled with 4-nitro-phenol, e.g. in the presence of an alkali hydroxide or alkali carbonate or an acid binding agent; or -the substituted halogeno benzotrifluoride is coupled under similar conditions with phenol and the coupled "intermediate" (which is an efficient fungicide per se) is subjected to subsequent nitration by a known nitrating method.

According to a further aspect of the present invention there are provided pesticidal compositions comprising as active ingredient at least one compound of the general Formula (I) in admixture with suitable inert solid or liquid carriers and/or diluents and optionally further auxiliary agents.

The pesticidal compositions of the present invention may be formulated in usual forms, e.g. as wettable powder (WP), suspension concentrates (SC), emulsifiable concentrates (EC), ultra low volume (ULV) forms etc.

The auxiliary agents may be e.g. surfactants, such as wetting, suspending, dispersing, emulsifying, anticoagulating, anti-caking agents, adhesive, spreaders, penetration increasing agents, additives suitable for maintaining or increasing the biological effect, antifoam agents etc. As suitable solid carriers and diluents e.g. inactive minerals such as various kaolins and China-clay, porcelain earth, attapulgite, montmorillonite, pyrophilite, bentonite, diatomaceous earth or highly dispersed silicic acids, calcium carbonate, calcinated magnesium oxide, dolomite, gypsum, tricalcium phosphate, Fuller's earth etc. may be used. Further suitable solid carriers and diluents are ground tobacco stem, wood meal, etc.

The following liquid diluents may be preferably applied: water, mixtures or organic solvents or water and organic solvents, e.g. methanol, ethanol, n- or isopropanol, diacetone alcohol, benzyl alcohol, glycols, e.g. ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and esters thereof such as methyl cellosolve; butyldiglycol, ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone etc; esters e.g. ethyl acetate, npropyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, isopropyl myristate, dioctyl phthalate, dihexyl phthalate etc; aromatic, aliphatic or alicyclic hydrocarbons, cyclohexane, kerozene, gasoline, benzene, toluene, xylene, tetraline, decaline; mixture of alkyl benzenes; chlorinated hydrocarbons e.g. trichloro ethane, dichloro methane, perchloro ethylene, dichloro propane, chloro benzene etc; lactones e.g. ^-butyrolactone, etc; lactames e.g. N-methylpyrrolidone, N-cyclohexyl-pyrrolidone; acid amides, e.g. dimethyl formamide etc; vegetable and animal oils e.g. sunflower weed, oliva, soya, flax, rape or castor oil, sperm oil stc.

The wetting, dispersing and emulsifying, anti-aggregating, anti-caking agents, adhesives and spreaders may be of ionic or non-ionic character. From the group of ionic agents the following compounds may be e.g. mentioned: salts of various saturated or unsaturated aromatic hydrocarbons; sulfates of alkyl, aryl or aralkyl alcohols; sulfonates of acids, alkyl, aryl or aralkyl esters or ethers; sulfonates of condensation products of phenol, cresol and naphthalene; sulfatated vegetable and animal oils; alkyl, aryl or aralkyl phosphate esters; and salts of the above compounds formed with alkali or alkaline earth metals or organic bases (e.g. amines, alkanolamines etc).

Thus e.g. sodium lauryl sulfate, sodium-2-ethyl-hexyl sulfate, the sodium, ethanol amine, diethanol amine, triethanol amine, or isopropyl amine salt of dodecyl-benzene sulfonic acid; sodium mono-and diisopropyl-naphthalene sulfonate; sodium naphthalene sulfonate; sodium diisooctyl sulfosuccinate; sodium xylene sulfonate; the sodium or calcium salt of petroleum sulfonic acid; potash soaps; sodium, calcium, aluminium or magnesium stearate etc. The phosphate esters may be esters of phosphatated alkyl phenols or fatty alcohols formed with polyglycol and different forms thereof partially or completely neutralized with cations or organic bases. Further suitable anionic surfactants are the disodium-N-octadecyl-sulfosuccinate, sodium-N-oleyl-N-methyl-tauride and various lignosulfonates.

As non-ionic wetting, dispersing and emulsifying etc. agents the following compounds may be advantageously used: ethers of ethylene oxide formed with C,0 20 alcohols such as stearyl polyoxyethylene, oleyl-polyoxyethylene; ethers formed with alkyl phenols e.g. polyglycol ethers formed of tertiary butyl, octyl or nonyl phenol; esters formed with various organic acids e.g polyethylene glycol ester of stearic acid or miristic acid, polyethyl glycol oleate etc; block polymers of ethyl oxide and propylene oxide; partial esters of fatty or oleic acids formed with hexitol anhydrides, e.g. esters of sorbitol formed with oleic acid or stearic acid; condensation products of the above compounds formed with ethylene oxide; tertiary glycols e.g. 3,6-dimethyl4-octin-3,6-diol or 4,7-dimethyl-5-decin-4,7-diol; polyethyl glycol thioethers e.g. ether of dodecyl mercaptane formed with polyethylene glycol etc. As adhesives e.g. alkaline earth metal soaps, salts of sulfosuccinic acid esters, natural or artificial water soluble macromolecules e.g. casein, starch, vegetable gums, arabic gum, cellulose ethers, methyl cellulose, hydroxyethyl cellulose, polyvinyl pyrrolidone, polyvinyl alcohol etc. may be used. As antifoam agents e.g. low molecular weight polyoxyethylene, polyoxypropylene block polymers (the number of the octyl, nonyl, phenyl-polyoxyethylene ethylene oxide units is > 5); long chain alcohols e.g. octyl alcohol; special silicon oils, etc. may be used.

The use of suitable additives enables the colloidal-chemical compatibility of the pesticidal compositions of the present invention with various fertilizer systems. The compositions of the present invention may also comprise further pesticidal active ingredients and/or nutrients.

The wettable powders (WP) may be prepared by admixing the active ingredient(s) and auxiliary agent(s), surfactant(s) with the carriers and grinding and homogenizing the mixture. If a liquid surfactant is used, one may also proceed by suspending the previously ground solid components in an organic solvent which comprises liquid surfactant(s) whereupon the suspension may be dried e.g. by spray-drying. Thus the surfactant is applied onto the surface of the solid active ingredient and the solid carrier.

An emulsifiable concentrate (EC) being auto-emulsifying and suitable for the preparation of an aqueous emulsion can be prepared by dissolving the active ingredient or a mixture thereof with the above surfactants and emulsifiers in a water non-miscible solvent. The emulsifiable concentrate thus obtained forms spontaneously or under mechanical effect a spray which remains unchanged and is stable even after long storage.

Water miscible solvent concentrate (SL) can be prepared by dissolving the active ingredient and suitable water-soluble auxiliary agents in water and/or a water-miscible solvent. On diluting with water a spray having the desired concentration may be prepared.

By selecting a suitable emulsifying agent the aqueous solution-concentrate of the active ingredient can also be dispersed in a water immiscible solvent to yield a so-called inverted emulsion.

The suitable and proper selection of the solvent and the surfactant enables the preparation of compositions which, on admixing with water or a water immiscible liquid, form a dispersed-e- ven molecularly dispersed-system which remains unchanged and stable after long storage.

A suspension concentrate (SC) may be prepared dissolving the wetting and dispersing agents in a mixture of water (preferably ion-exchanged water) and an antifreeze component (preferably ethylene glycol or glycerol) if necessary under warming. To the solution thus obtained the solid (powdered or crystalline) active ingredient(s) and if necessary the anti-caking component (e.g.

Aerosil 200) are added under constant stirring. The granule-liquid system thus obtained (slurry) is ground in a grinding apparatus (e.g. closed Dyno-mill) to the desired particle size i.e. generally to below about 5 micrometers to ensure a good and safe storing stability. After grinding an antifoam or thickening agent (e.g. Kelzan S) is added, if necessary, during the homogenizing procedure. One may also proceed by changing the order of succession of the mixing of the components or adding further components, too (e.g. dyestuffs). In addition to the solid carrier liquid, water immiscible or water-miscible active ingredients may be introduced as combination partner. Solid active ingredients having a low melting point may be introduced also in the form of a melt in the presence or absence of an emulsifier.The ULV compositions may be prepared similarly to the EC and sometimes the SC formulations.

Granules (G) suitable for direct use may be prepared by means of extruding and lamination from a granular carrier (e.g. ground limestone) or by absorbing the liquid component by a carrier having a sorption capacity.

Granules (WG) suitable for spraying purposes can be prepared from WP and/or SC formulations with the aid of an agglomerizing technology (e.g. in a drag e pan by using a binding agent).

Spray or dusting compositions suitable for direct use in agriculture can be prepared from the above formulations by diluting with water or an inert solid carrier. The active ingredient content of the said ready-for-use compositions is generally below 5% by weight and is preferably 0.01-1% by weight. One may also proceed by admixing several sprays comprising one active ingredient before use.

Further details of the present invention are to be found in the following Examples without limiting the scope of protection to the said Examples. The preparation of the new substituted phenoxy benzaldehyde intermediates is also disclosed. For the sake of better understanding the substituent definition and physical constants of the compounds described in the Examples are summarized in Table 1.

Table 1.

Example X Y Z V W R R Mp. ( C) No.

1 Cl H CF3 H H H CH3 89-92 2 NO2 H CF3 Cl H H CH3 141-148 3 Cl H CF3 H Cl H CH3 115-125 4 CF3 H H H H H C6H5 146-148 5 Cl H CF3 H H H C6H5 146-150 6 NO2 H CF3 Cl H H C6H5 162-164 7 NO2 H CF3 H NO2 H C6H5 228-231 8 Cl H CF3 H Cl H C6H5 182 9 CF3 H CF3 H NO2 H C6H5 148-152 10 Cl H CF3 H H NO2 CH3 145-146 11 Cl H CF3 H Cl NO2 CH3 121-130 12 Cl H CF3 H H NO2 C2H5 145-146 13 Cl H CF3 H H NO2 C6H5 172-176 14 NO2 H CF3 H H NO2 C6H5 193-195 15 NO2 H CF3 H NO2 NO2 C6H5 196-201 Table 1.

(contd.) Example X Y Z V W R R Mp. ( C) No.

16 Cl H CF3 H Cl NO2 C6H5 167-169 17 CF3 H NO2 H NO2 NO2 C6H5 166-167 18 Cl H CF3 H H NO2 3-Cl-C6H5 172-173 Example 1 4-{3-[(2-chloro-4-trifluoromethyl)-phenoxy]-benzylidene}-2-methyl-oxazoline-5-one (Compound No. 1) 5.5 g (0.018 moles) of 3-[(2-chloro-4-trifluoromethyl)-phenoxy]-benzaldehyde, 3.21 g (0.027 moles) of N-acetyl-glycine, 1.05 g (0.013 moles) of anhydrous sodium acetate and 4.67 g (0.048 moles) of acetic anhydride are introduced into an Erlenmeyer-flask; cotton-wool is placed into the neck of the said Erlenmeyer-flask. The reaction mixture is stirred on an oil-bath having a temperature of 100"C for 3 hours. During stirring yellow crystals gradually precipitate and at the end of the reaction time the solution is transformed into a thick suspension.This suspension is allowed to stand overnight, thereafter thoroughly admixed with 80 ml of water and 100 g of ice and the precipitate is filtered. The product is washed with 150 ml of water, 40 ml of pentane and cold alcohol and dried. Thus 6.0 g of the desired compound are obtained, yield 87.5%.

Brutto Formula (calc.) C,8H1,CIF3NO3.

Molecular weight: 381 Yellowish-brown crystals, mp.: 89-92"C.

Characteristic fragmens of the mass spectrum: m/e (r.i)=381 (300 F3C(Cl)C6H3OC6H4CHC(CO)N(O)CCH3 291 (600) F2C(Cl)C6H3OC6H4CHCN 43 (1000)=CH3CO Characteristic bands of the 'H-NMR spectrum: a cH3=2.30 (s), the aromatic protons give a complex multiplet (a=6.9-7.87 ppm) Characteristic bands of the IR spectrum: v C=0=1790, 1770 cm-', v C=N=1660 cm-1, v as C-O-C= 1320 cm-1.

Example 2 4-j3-[(5-chloro-4-trifluorome th yl-2-nitro)-phenoxy]-benzylidenel-2-meth yl-oxazoline-5-one (Compound No. 2) (a) One proceeds according to Example 1 except that 3-[(5-chloro-4-trifluoromethyl-2-nitro)- phenoxy]-benzaldehyde is used as starting material.

Yield 82.9% Brutto Formula: (Calc.) C,8H10ClF3N205 Molecular weight: 426.

The yellow crystals melt at 141-148"C.

The mass spectrum confirms the above structure.

m/e (r.i.) =426(320) =F3C(NO2)ClC6H2OC6H4CHC(CO)N(O)CCH3 224(250) = F3C(NO2)CIC6H2 43(1000) = CH3CO In the 'H-NMR spectrum the singulet of the CH3 proton (a=2.28 ppm) and that of the H3 aromatic proton (#=8.25) are well identifiable while the other aromatic protons give complex multiplet at 7.0-9.87 ppm.

In the IR spectrum at 1805 and 1775 cm-' two v C=O bands of approximately identical intensity appear. The v C=N band gives- an overlapping doublet sign (1600 cm-'). The splitting of the v as C-O-C (1300 cm-') refers to the presence of two isomers.

(b) 7.8 g (0.03 moles) of 2,4-dichioro-5-nitro-benzotrifluoride 4.4 g (0.036 moles; a molar excess of 20%) of 3-hydroxy-benzaldehyde and 4.97 g (0.036 moles) of anhydrous potassium carbonate are added to 50 ml of anhydrous acetone and the suspension is stirred at room temperature for 16 hours. The reaction mixture is filtered, dissolved in isopropanol at boiling point and the solution is slowly cooled under stirring. Thus 8.0 g of the crystalline product are obtained, yield 77%, mp.: 80-83"C.

Example 3 4-{3-[(2.7-dichloro-4-trifluoromethyl)-phenoxy]-benzylidene}-2-methyl-oxazoline-5-one (Compound No. 3) One proceeds according to Example (1a) except that 3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzaldehyde is used as starting material.

Yield: 90%.

Brutto Formula (calc): C,8H,oCI2F3NO3 Molecular weight: 415.

The yellow crystals melt at 115-125"C.

The mass spectrum of the compound shows the characteristic fragments of compounds comprising two chlorine atoms.

m/e (r.l.)=419 (110)=F3C(Cl)2C6H2OC6H4CHC(CO)N(O)CCH3 418 (110) = F3C(Cl)2C6H20C6H4CHC(CO)CCH3 417 (580)=F3C(Cl)2C6H2OC6H4CHC(CO)N(O)CCH3 416 (180) = F3C(Cl)2C6H2OC6H4CHC(CO)N(O)CCH3 415 (850)=F3C(Cl)2C6H2OC6H4CHC(CO)N(O)CCH3 43 (1000)=CH3CO Characteristic bonds of the 'H-NMR spectrum: # CH3=2.25 (s), b35=7.625 (s), #2, = 7.62 (d, J26=3 Hz), b5=7-25 (d, J5,6=9 Hz), d6,=6.85 ppm (dd, J6,5,=9 Hz, J62=3 Hz).

Characteristic bonds of the IR spectrum: v C=0=1770 and 1800 cm-1, v C=N=1650 cm-1, v as C-O-C=1320 cm-1, v s C-O-C=1125 cm-1, Example 4 4-{3-[(2-trifluoromethyl)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one (Compound No. 4) (a) 8.0 g (0.0276 moles) of 3-[(2-trifluoromethyl)-phenoxy]-benzaldehyde, 4.95 g (0.027 moles) of hyppuric acid and 2.26 g (0.027 moles) of anhydrous sodium acetate are weighed into an Erlenmeyer-flask, whereupon 4.22 g (0.0414 moles) of acetic anhydride are added. The suspension is stirred on a hot water-bath for 2 hours. A warm homogenous solution is obtained from which slowly yellow crystals precipitate. The reaction mixture is allowed to stand at roomtemperature overnight. The product thus obtained is suspended in 20 ml of anhydrous ethanol, filtered and washed with cold ethanol.Thus 8.9 g of the desired compound are obtained, yield 79%.

Brutto Formula (calc): C23H,4F3NO3.

Molecular weight: 409.

The yellow crystals melt at 146-148 C.

The mass spectrum of the compound is but very poor in bands. In addition to the molecular ion only the benzoyl and phenyl group appear with an intensity which can be still evaluated.

m/e (r.i.) =409 (270) = F3CC6H40C6H4CH(CO) N(O)C(C6H5) 105 (1000)=QH5CO 77 (210)=C6H5 In the IR spectrum of the compound the v 0=0 band appears at 1780 cm-1, the Vas C-O-C band at 1320 cm-1, the v5 C-O-C band at 1130 cm ' and the v 0=N band at about 1650 cm-1.

(b) 34.6 g of (0.2084 moles) of 3-hydroxy-benzaldehyde-ethylene acetate are dissolved in 100 ml of anhydrous methanol and a solution of 11.69 g (0.2084 moles) of potassium hydroxide in 100 ml of anhydrous methanol is added. The methanol is removed from the reaction mixture after a short stirring period by suction. To the residue 31.5 g (0.1876 moles) of 2chloro-benzotrifluoride and 100 ml of anhydrous dimethyl sulfoxide are added and the solution is refluxed for 200 hours, whereupon 60 ml iof dimethyl sulfoxide are removed in a water-pump vacuo. The residue is extracted three times with 150 ml of methylene chloride each. The dichloro methane extract is washed with a 0.5 N sodium hydroxide solution and a concentrated sodium chloride solution, dried over magnesium sulfate and evaporated. Thus 14.0 g of a liquid are obtained, yield 22.0%.

(c) 14.0 g (0.045 moles) of 3-[(2-trifluoromethyl)-phenoxy]-benzaldehyde-ethylene acetale are dissolved in 300 ml of acetone and 75 g of 10% hydrochloric acid are added. The reaction mixture is heated at the boiling point of acetone for 3 hours, whereupon the acetone is removed, the residue is extracted twice with 100 ml of methylene chloride, the organic phase is washed twice with 100 ml of water, dried over magnesium sulfate and the methylene chloride is removed. Thus 8.0 g of a brown liquid are obtained, yield 57.3%.

Example 5 4-{3-[(2-chloro-4-trifluoromethyl)-phenoxy]-benzylidene]}-2-phenyl-oxazoline-5-one (Compound No. 5.) One proceeds according to Example 4 except that 3-[(2-chloro-4-trifluoromethyl)-phenoxy]benzaldehyde is used as starting material. Yield: 78.2%.

Brutto Formula (calc): C23H13CIF3NO3 Molecular weight 443.

The yellow crystals melt at 146-150 C.

The mass spectrum of the compound is very poor in bands.

m/e (r.i.)=443 (120=F3C(Cl)C6H3OC6H4CHC(CO)N(O)(C6H5) 105(1000)=C6H5CO 77 (220)=C6H5 The 1H-NMR spectrum shows complex multiplet characteristic of aromatic protons.

In the IR spectrum the V as C-O-C (1320 cm-'), vs C-O-C (1110 cm-'), v C=N (1650 cm-1), v 0=0 (1780 cm-1) bands are well recognizable.

Example 6 4-{3-[(5-chloro-4-trifluoromethyl-2-nitro)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one (Compound No. 6.) 6.9 g (0.02 moles) of 3-[(5-chloro-4-trifluoromethyl-2-nitro)-phenoxy]-benzaldehyde, 3.6 g (0.02 moles) of hyppuric acid, 1.65 g (0.02 moles) of anhydrous sodium acetate and 10.3 g (0.1 moles) of acetic anhydride are weighed into an Erlenmeyer-flask. The reaction mixture forms at 60 C a crystalline mass. The suspension is heated in a hot water-bath for 2 hours, then cooled, whereupon 20 ml of ethanol are added and the mixture is allowed to stand in a refrigerator. The precipitated product is filtered and washed at first with cold water and then with warm (50 C) water. Thus 6.4 g of the desired compound are obtained, yield 65.3%.

Brutto Formula (calc): C23HI2CIF3N205 Molecular weight 488.

The light yellow crystals melt at 162-164 C Characteristic fragments of the mass spectrum: m/e (r.i.) =488 (170) =F3C(NO2)(Cl)C6H2OC6H4CHC(CO)N(O)(C6H6] 105 (1000)=CsH5CO 77 (220)=C6H5 In the 1H-NMR-spectrum the aromatic protons give a complex multiplet in the interval of 7.0-8.0 ppm and only the singulet of the H3 proton is easily recognizable (a=8.25 ppm).

In the IR spectrum the following characteristic bands appear: v C-O=1790 cm-', v C=N=1650 cm-1.

Example 7 4-{3-[(4-trifluoromethyl-2,60-dinitro)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one (Compound No.

7).

(a) 8.9 g (0.025 moles) of 3-[(4trifluoromethyl-2,6-dinitro)-phenoxy]-benzaldehyde, 4.5 g (0.025 moles) of hyppuric acid, 2.05 g (0.025 mole) of anhydrous sodium acetate and 16 g (0.158 moles) of acetic anhydride are weighed in an Erlenmeyer-flask. The reaction is carried out and the reaction mixture is worked up as described in Example 6. Thus 8.8 g of the desired compound are obtained, yield 70.6%.

Brutto Formula (calc): C23H,2F3N307 Molecular weight: 449 The yellow crystals melt at 228-231 C.

In the 'H-NMR spectrum the H3 and H5 protons give the most intensive, identifiable signals (8.45 ppm) while the other aromatic protons show a complex multiplet at 7.0-8.0 ppm.

Characteristic bands of the IR spectrum: v CO=1780 cm-1, v C=N=1650 cm-', V55 NO2=1530 cm-1, V55 C-0-C=1310 cm-', vs C-O-C=1130 cm-1, (b) One proceeds according to Example 2/b except that in the place of 2,4-dichloro-5-nitrobenzotrifluoride the 3,5-dinitro-4-chlorobenzotrifluoride is used as starting material. Yield: 9.5 g, 89%. M.p.: 1301310C.

Example 8 4-{3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one (Compound No. 8) 8.5 g (0.0257 moles) of 3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzaldehyde, 4.6 g (0.027 moles) of hyppuric acid, 2.1 g (0.0256 moles) of anhydrous sodium acetate and 16 g (0.157 moles) of acetic anhydride are weighed in an Erlenmeyer-flask. The suspension is stirred on a hot water-bath for an hour. After cooling a crystalline mass is obtained which is suspended in water, filtered and the precipitate is washed with water. After recrystallization from ethanol 9.8 g of the desired compound are obtained in the form of light yellow crystals, yield 81%.

Brutto Formula (calc): C23H120l2F3NO3.

Molecular weight 477.

The light yellow crystals melt at 182 C.

The mass spectrum of the sample shows the characteristic fragments of compounds comprising two chlorine atoms.

m/e (r. i.) = 480 (15) = F3C(Cl)C6H2OC6H4CHC(CO)N(O)C(C6H5) 479 (80)=F3C(Cl)C6H2OC6H4CHC(CO)N(O)C(C6H5) 478 (30)=F3C(Cl)C6H2OC6H4CHC(CO)N(O)C(C6H5) 477 (100)=F3C(Cl)C6H2OC6H4CHC(CO)N(O)C(C6H5) 105 (1000) =C6H5CO 77 (230)=C6H5 Characteristic bands of the IR spectrum: v C=0=1780 cm-1, v C=1C1=1640 cm-', vaS C-O-C=1310 cm-1, vs C-O-C=1120 cm-1.

In the 1H-NMR spectrum from the complex multiplet appearing at 6.87-8.0 ppm the singulet of the H3 and H5 protons (a=7.63 ppm) is easily identifiable.

Example 9 4-{3-[(2-trifluoromethyl)-4,6-dinitro-phenoxy]-benzylidene}-2-phenyl-oxazolin-5-one (Compound No.

9) (a) 8.9 g (0.025 moles) of 3-[(2-trifluoromethyl-4,6-dinitro)-phenoxy]-benzaldehyde, 4.5 g (0.025 mole) of hyppuric acid and 2.05 g (0.025 mole) of acetic anhydride are weighed in an Erlenmeyer-flask. The reaction is carried out and the reaction mixture worked up as described in Example 6. Thus 9.0 g of the desired compound are obtained, yield 72%.

Brutto Formule (calc): C23H,2F3N307 Molecular weight: 499 The brownish yellow crystals melt at 148-152 C.

The mass spectrum shows a fragmentation mechanism somewhat more varied than in the previous cases and also the fragments due to the splitting of the ether group appear: m/e (r.i.) =499 (110) = F3C(NO2)2C6H2OC6H4CHC(CO)N(O)C(C6H5) 307 (180)=F2C(NO2)2C6HOC6H4 235 (1 20)=F3C(NO2)2C6H2 105 (1000)=C6H5CO In the 'H-NMR spectrum the dublet of the H5 and H3 protons clearly separate [a5=8.98 ppm (d, J53=3 Hz), (53=8.80 ppm (d, J35=3 Hz), the other aromatic protons give a complex multiplet in the range of 6.9-7.85 ppm.

Characteristic bands of the IR spectrum: v CO=1780 cm-', v C=N=1535 cm-', v5 C-O-C=1140 cm-1.

(b) One proceeds according to Example 2b) except that 2,4-dichloro-5-nitro-benzotrifluoride is replaced by 2-chloro-3,5-dinitro-benzotrifluoride. Yield 8.1 g, 76%, Mp.: 104"C.

Example 10 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5-one (Compound No. 10) 34.5 g (0.1 moles) of 5-[(2-chloro-4-trifluoromethyl)-phenoxy]-benzaldehyde, 17.5 g (0.15 moles) of N-acetyl-giycine, 5.7 g (0.07 moles) of anhydrous sodium acetate and 25.5 g (0.25 moles) of acetic anhydride are weighed in an Erlenmeyer-flask. Cotton-wool is placed into the neck of the flask and the reaction mixture is stirred at 100 C for an hour on an oil-bath and thereafter allowed to stand over-night. The thick suspension is stirred in 80 ml of cold isopropanol and filtered. Thus 34.0 g of the desired compound are obtained, yield 79.6%.

Brutto Formula (calc): C16H10ClF3N2O5 Molecular weight: 426.

The yellowish-brown powder melts at 145-146 C.

The characteristic fragments of the mass spectrum are as follows: m/e (r.i.) = 426 (280) = F3C(Cl)C6H3OC6H3(NO2)CHC(CO)N(O)(CCH3 413 (600)=F3C(CI)C6H30C6H3(NO)CH 43 (1000) = CH3CO Characteristic bands of the 'H-NMR spectrum: CH3=2.25 ppm, the aromatic protons give a complex multiplet signs between 6.9 and 8.12 ppm.

Characteristic bands of the IR spectrum: v C=0=1795, 1765 cm-', v C=N=1650 cm-', Vas C-O-C=1320 cm-1, vs C-O-C=1150 cm-1.

Example II 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidee}-2-methyl-oxazoline-5-one (Compound Nr. 1 1) 6.0 g (0.0158 moles) of 5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzaldehyde, 2.8 g (0.027 moles) of N-acetyl-glycine, 0.9 g (0.0111 moles) of anhydrous sodium acetate and 4.0 g (0.0395 moles) of acetic anhydride are weighed in an Erlenmeyer-flask. The reaction mixture is stirred on an oil-bath having a temperature of 10000 for 2 hours and allowed to stand at room temperature overnight. The melt is dissolved in 50 ml of carbon tetrachloride, the organic phase is washed twice with 100 ml of water each, dried over magnesium sulfate and the product is precipitated by adding hexane, filtered and washed with hexane. Thus 6.0 g of the desired compound are obtained, yield 82.5%.

Brutto Formula (calc.) C,8HgC12F3N202 Molecular weight 460.

The greenish yellow crystals melt at 121-130 C Identifiable signs of the 'H-NMR spectrum: #CH3=2.25 (s), (535=7.68 (s), #2'=7.60 (d, 3Hz), #5'=8.06 (d, J5',6'=9 Hz), #6' = 6.96 ppm (dd, J5'6'=9 Hz, J6'2'=3 Hz).

Characteristic bands of the IR spectrum: v C=0=1805 and 1760 cm-', v C=N=1650 and 1645 cm-', vas C-0-C=1320, v5 C-0-C=1130 cm-'.

Example 12 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-ethyl-oxazoline-5-one (Compound No. 12) One proceeds according to Example 10 except that N-acetyl-glycine is replaced by N-propionylglycine.

Yield 72%.

Brutto Formula (calc.): C,9H,2ClF3N205 Molecular weight 440.

The yellow powder melts at 145-146 C.

Characteristic fragments of the mass spectrum: m/e (r.i.)=440 (300)=F3C(Cl)C6H3OC6H3(NO2)CHC(CO)N(O)CC2H 313 (580) = F3C(CI)C6H30C6H3(NO)CH 57 (1000)=C2HsCO Identifiable signs of the 'H-NMR spectrum: #CH3 = 1.25 (tr, 7 Hz), #CH2=(q, 7 Hz), the aromatic protons give a complex multiplet at 7.0-8.07 ppm.

Characteristic bands of the IR spectrum: v C=0=1780 cm-', C=N=1650 cm-', vaS C-0-C=1320 cm-', vs C-O-C=1150 cm-'.

Example 13 4-R'51(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzZlidenel!-2-phenyl-oxazoline-5-one (Compound No. 13) 6.9 g (0.02 moles) of 5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzaldehyde, 3.6 g (0.02 moles) of hyppuric acid, 1.44 g (0.02 moles) of anhydrous sodium acetate and 10.3 g (0.1 moles) of acetic anhydride are weighed into an Erlenmeyer-flask. The reaction mixture is heated under stirring on a hot water-bath for 2 hours, then cooled, suspended in 20 ml of anhydrous ethanol and allowed to stand in a refrigerator overnight. The suspension is filtered and the precipitate is washed with cold ethanol. Thus 7.5 g of the desired compound are obtained, yield 76.8%.

Brutto Formula (calc.): C23H,2CIF3N205 Molecular weight: 488 The yellow crystals melt at 172-176 C.

m/e (r.i.) = 448 (90) = F3C(Cl)C6H3OC6H3(NO)2CHC(CO)N(O)C(C6H5 313 (500)=F3C(Cl)C6H3OC6H3CH(NO) 285 (60) = F3C(CI)C6H30C6H4N 105 (1000)=C6H5CO 77 (550)=C6H5 In the 'H-NMR spectrum the aromatic protons give a complex multiplet (a=7-8.1 ppm) Characteristic bands of the IR spectrum: v C=0=1790 cm-1 (dublet) v C=N=1650 cm-1 (dublet), vaS NO2=1520 cm-', Vas C-O-C=1330 cm-1, vs C-O-C=1170 cm-1. The The splitting of the individual bands to dublet can be explained by the presence of two isomers.

Example 14 4-(5-[(4-trifluoromethyl-2-n!tro)-phenoxy]-2-nitro-benzylidenei-2-phenyl-oxazollne-5-one (Compound No. 14) (a) One proceeds according to Example 13 except that 5-[(4-trifluoromethyl-2-nitro)-phenoxy]benzaldehyde is used as starting material.

Yield 70%.

Brutto Formula (calc.): C23H,2N307 Molecular weight: 499 The yellow crystals melt at 193-195 C.

Characteristic fragments of the mass spectrum: m/e (r.i.) = 499 (20) = F3C(NO2)C6H3OC6H3(NO2)CHC(CO)N(O)C(C6H5) 324 (120) = F3C(NO2)C6H30C6H3CH(NO) 134 (500)=C6H3(CH)NO2 105 (1000)=C6H6CO 77 (320)=C6H5 In the 'H-NMR spectrum a complex multiplet appears in the range of the aromatic protons (#=7.5-8.76).

In the IR spectrum an interesting splitting of Vco (1780, 1790 cm-1) and VC=N (1650, 1645 cm-1) can be observed which can be explained by the presence of the 0=0 cis-trans isomers.

(b) 33.2 g (0.2 mole) of 3-hydroxy-benzaldehyde-ethylene acetale are reacted with 11.2 g (0.2 moles) of potassium hydroxide to yield the potassium phenolate derivative, to which 100 ml of dimethyl sulfoxide and 40.14 g (0.18 moles) of 4-chloro-3-nitro-benzotrifluoride are added and the reaction mixture is stirred at 110-115 C for 4 hours. The majority of the solvent is distilled off, the residue is suspended in 150 ml of methylene chloride and filtered (the major part of the precipitate consists of potassium chloride). The organic phase is washed with an aqueous sodium chloride solution, a 0.5 N sodium hydroxide solution and again a sodium-chloride solution, dried over magnesium sulfate and the methylene chloride is removed in a water-pump vacuo. Thus 58.0 g of an oily residue are obtained, yield 91.2%.

(c) 20 g (0.056 moles) of 3-[(4-trifluoromethyl-2-nitro)-phenoxy]-benzaldehyde-ethylene acetale are dissolved in 200 ml of methanol and 100 g of a 2% hydrochloric acid solution are added.

The solution is refluxed for 4 hours, the acetone is removed and the residue is extracted twice with 200 ml of methylene chloride each. The organic phase is washed twice with 100 ml of water, dried over magnesium sulfate and the methylene chloride is removed. The oily residue is crystallized from a 4:1 mixture of isopropanol and methanol. Thus 16.3 g of the desired compound are obtained, yield 91%, mp.: 48-49"C.

(d) 48.4 g (0.155 moles) of 3-[(4-trifluoromethyl-2-nitro)-phenoxy]-benzaldehyde are dissolved in a mixture of 100 ml of methylene chloride and 80 ml of acetic anhydride. The solution is cooled to 0 C and nitrating acid (a mixture of 16.2 ml (0.234 moles) of 65% nitric acid and 19.2 ml (0.366 moles) of 96% sulfuric acid) is added dropwise. The solution is stirred and the temperature is kept by cooling under +8 C. The addition having been completed the reaction mixture is stirred at room temperature for 3 hours. The methylene chloride is distilled off, the residue is poured onto 300 g of crushed ice. On standing for a night the product solidifies. The precipitate is filtered off, thoroughly washed with water and recrystallized from a 1:1 mixture of methanol and isopropanol.Thus 32.0 g of the desired compound are obtained, yield 44.9%, mp.: 78-82"C.

(e) 48.2 g (0.105 moles) of 5-[(4-trifluoromethyl-2nitro)-phenoxy]-2-nitro-benzaldehyde-diace- tate are dissolved in 400 ml of technical grade acetone, whereupon 230 g of 10% hydrochloric acid are added. The reaction mixture is refluxed for 7 hours and the majority of the acetone is distilled off. The aqueous residue is extracted twice with 100 ml of methylene chloride each, the solvent is removed, the residue is dissolved in ether and the product is precipitated by adding hexane. The solid is recrystallized from isopropanol. Yield 25.7 g, 68.6%. Mp.: 95-97"C.

Example 15 4-{5-[(4-trifluoromethyl-2,6-dinitro)-phenoxy]-2-nitro-benzylidene}-2-phenyl-oxazoline-5-one (Compound No. 15) (a) One proceeds according to Example 13 except that 5-[(4-trifluoromethyl-2,6-dinitro)-phenoxy]-2-nitro-benzaldehyd is used as starting material.

Yield 49.3%.

Brutto Formula (calc): C23H11F3N4O9 Molecular weight: 544 The yellow crystals melt at 196-201 C.

The mass-spectrum shows the fragmentation mechanism characteristic of this compound-type.

m/e (r. /i.) = 544 (210) = F3C(NO2)2C6H2OC6H3(NO2) CHC(CO)N(O)C(C6H5) 405 (470)=F3CC6H3OC6H3CHC(CO)N(O)C(C6H5) 369 (720)=F3C(NO2)20C6H3CH(NO) 134 (35)=C6H3(CH)NO2 105 (1000)=C6H5CO In the IR spectrum VC=O 1790 cm-1 and VCCN 1650 cm-'.

Due to the presence of the three nitro groups intensive bands appear at 1550, 1330 and 1150 cm-1.

(b) 6.05 g (0.017 moles) of 3-[(4-trifluoromethyl-2,6-dinitro)-phenoxy]-benzaldehyde (prepared according to Example 2b) are dissolved in a mixture of 12.5 ml of dichloro methane and 7.6 9 of acetic anhydride, the solution is cooled to 10 C and nitrating acid [a mixtures of 1.8 ml (0.027 moles) of 65% nitric acid and 1.8 ml of 98% sulfuric acid] is added dropwise. Yield 4.1 9, 60%. Mp.: 129-130 C.

Example 16 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzyliden}-2phenyl-oxazoline-5-one One proceeds according to Example 13 except that 5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]- 2-nitro-benzaldehyde is used as starting material.

Yield 79%.

Brutto Formula (calc.) C23H1,C12F3N205 Molecular weight: 522 The yellowish-brown crystals melt at 167-169 C.

Characteristic fragments of the mass spectrum: m/e (r.i.) 522 (70)=F3C(Cl)2C6H2OC6H3(NO2)CHC(CO)N(O)C(C6H5) 347 (320)=F3C(CI)2C6H20C6H3CH(NO) 105 (1000)=C6H5 77 (530)=C6H5 Identifiable signs of the 'H-NMR spectrum: b35=7.55 (s), #2'=7.5 (d, J2'6'=2 Hz), #5'=8.15 (d, Jt'6'=9 Hz), d6=7.2 (dd, J6.5.= 9 Hz, J6.2.=2 Hz), #CH=7.5, #C5H6=7.9 ppm (complex multiplet).

Identifiable bands of the IR spectrum: u C=0=1800 cm--1, v C=N=1660 cm--1, Vas C-O-C=1320 cm--', Vs C-O-C=1150 cm 1.

Example 17 4-{5-[(2-trifluoromethyl-4,6-dinitro)-phenoxy]-2-nitro-benzyliden}-2-phenyl-oxazoline-5-one (Compound No. 17) (a) One proceeds according to Example 7 except that 5-[(2-trifluoromethyl-4,6-dinitro)-phenoxy]-2-nitro-benzaldehyde is used as starting material.

Yield 31%.

Molecular weight: 544 The brown powdery product melts at 166-167 C.

Characteristic fragments of the mass spectrum: m/e (r.i.)=544 (130)=F3C(NO2)2C6H2OC6H3(NO2)CHC(CO)N(O)(C6H5) 369 (760)=F3C(NO2)2C6H20C6H3CH(NO) 134 (330)=C6H3(CH)NO2 105 (1000)=C6H5CO 77 (500)=C6H5 In the 1H-NMR spectrum the H3 and H5 protons give a dublet (#3=8.8, #5=9.08, J35=3 Hz), while the other protons give a complex multiplet in the range of 7.0-8.2 ppm.

Characteristic bands of the IR spectrum: v C=0=1800 cm-1, v C=N=1660 cm-1, v5 C-O-C= 1150 cm-1, Vas NO2= 1520 and 1540 cm-'.

(b) 8.4 9 (0.024 moles) of 3-[(2-trifluoromethyl-4,6--dinitro)-phenoxy]-benzaldehyde is nitrated as described in Example 15b). Yield 6.0 g, 64%, mp.: 112-122 C.

Example 18 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-(3-chlorophenyl)-oxazoline-5-one (Compound No. 18) One proceeds according to Example 13 except that hyppruic acid is replaced by N-(3-chlorobenzoyl)-glycine. Yield 75.6%.

Brutto Formula (calc.): C22H1C12F3N205 Molecular weight: 522.

The yellow crystals melt at 172-173"C.

Characteristic fragments of the mass spectrum: m/e (r.i.) = 522 (100) =F3(Cl)C6H3OC6H3(NO2)CHC(CO)N(O)CC6H4Cl 313 (450) = F3C(CI)C6H30C6H3CH(NO) 139 (1000) = CIC6H4CO 111 (539)=C6H4CI In the 1H-NMR spectrum the aromatic protons give a complex multiplet in the range of 7.1-8.3 ppm.

Characteristic bands of the IR spectrum: v C=0=1705, 1780 cm 1, v C=N=1640, 1645 cm-1, V95 C-O-C=1310, 1320 cm 1.

Example 19 Granules (G) having a low active ingredient content Compound No. 1 0.010/o by weight Diaperl S1 99.99% by weight Diaperl S1 is a pearl granular silicic acid carrier having a high sorption capacity.

From the active ingredient solid granules having a low active ingredient content are prepared which can be applied without water. 2.3 g of technical grade active ingredient are dissolved in 97.7 g of methylene chloride. Into a Lodge 20 type whirling mixer (jet mixer) a pearl silicic acid carrier prepared from 4000 g of diatomaceous earth are placed (particle size 0.5-2 mm). 20 g of the active ingredient premix (2% by weight solution) are sprayed onto the granulated carrier by the aid of a Tee-Jet 10080 type spray-head with a speed of 5 g/min; in the Lödige-type mixer stirring is maintained at a rate of 50 r.p.m. The sorption type granules are finally packed.

The methylene chloride used for the preparation of the active ingredient premix is practically completely evaporated during the formulation procedure.

Example 20 Water dispersible granules (WG) having an active ingredient content of 49% by weight Compound No. 18 49% % by weight Cab-O-Sil M5 5% by weight Atlox 4862 3% by weight Polifon 0 6% by weight Geropon IN 5% by weight China-clay 32% by weight 123 g of compound No. 18, 12.5 g of Cab-O-Sil M5 (amorphous silicium dioxide), 7.5 g of Atlox 4862 dispersing agent (condensation product of naphthalene sulfonate and formaldehyde), 12.5 g of Geropon IN wetting agent (isopropyl naphthalene sulfonate) and 80 g of China-clay are admixed in a mortar. The mixture is ground in a JMRS-80 type whirling mill to a degree that the amount of the fraction above 44 micrometers should not exceed 0.5% by weight.The powder is admixed with a binder solution prepared from 15 g of Polifon 0 and 35 g of water in a Werner-type Kneading machine, whereupon an extruded granule is prepared by using a facing (diameter 1 mm) of an Alexanderwerke-type extruder and the product is dried in an air-current heater to 60."C.

Example 21 Wettable powder (WP) Compound No. 2 96% by weight Cab-O-Sil M5 1 % by weight Dispersing agent 1494 3% by weight 240 g of compound No. 2, 2.5 g of Cab-O Sil M5 (amorphous silicium dioxide) carrier and 7.5 g of dispersing agent (1494=sodium salt of the condensation product of sulfonated cresol and formaldehyde) are admixed in a mill equipped with a rotating knife. The powdered mixture is ground in an Alpine JMRS-80 type whirling mill under an injector air pressure of 5 bar, a grinding air pressure of 4.5 bar and a feeding rate of 250 g/h.The wettable powder thus obtained is readily wettable with water although it contains no additional wetting agent; maximal particle diameter 20 micrometers; floatilibty in a spray having a concentration of 10 g/l at 30"C after 30 minutes: 84% in CIPAC standard D water and 91% in CIPAC standard A water.

Example 22 Wettable powder (WP) Compound No. 13 77,3% by weight Cab-O-Sil M5 6 % by weight Geropon 1N 3 % by weight Polifon 0 5 % by weight China-clay 8.7% by weight 330 g of Cab-O-Sil M5 (amorphous silicium dioxide), 480 g of China-clay, 4250 g of compound No. 13 (previously ground in a hammer mill) are weighed in a Lodge M 20 type jet mixer and the active ingredient is homogenized with the carriers by stirring for 5 minutes. 165 g of Geropon IN wetting agent (isopropyl naphthalene sulfonate) and 275 g of Polifon 0 dispersing agent (sodium lignosulfonate) are weighed in and stirring is continued for a further period of 5 minutes. The powdered mixture is ground in an Alpine Z-160 type mill to a degree that the amount of the fraction above 44 micrometers should not exceed 0.1% by weight.

Example 23 ULV composition Compound No. 3 27.5% by weight Isophoron 30 % by weight 2-ethoxy-ethanol 10 % by weight Soya oil (or sunflower oil) 32.5% by weight 7500 g of isophoron and 2500 g of 2-ethoxyethanol (solvents) are weighed in a dry emailled autoclave. 6875 g of compound No. 3 (previously ground in a hammer mill) are added to the above solvent mixture and stirring is simultaneously started. Temperature is raised to 45-50"C with the aid of the mantle heating of the autoclave. An hour later-after all the active ingredient has been dissolved-8125 g of soya oil (or sunflower oil) are added, stirring is continued for 2 hours and the mixture is cooled back to 20 C. The ULV composition is applied in undiluted form without any addition of water.

Example 24 ULV composition Compound No. 10 10.3% by weight Cyclohexanone 25 % by weight Solvesso 200 12.5% by weight Sunflower oil 52.2% by weight A 22% by weight solution of compound No. 10 is prepared by dissolving the said active ingredient in a 2:1 mixture of cyclohexanone and Solvesso 200 (aromatic solvent) under stirring.

The solution is diluted to 10% by weight with sunflower oil (to 578 g of the compound 522 g of oil are added).

Example 25 Oily suspension concentrate (FO) Compound No. 6 32.7% by weight Cosmetical oil 48.8% by weight Tensiofix AS 4 % by weight Sapogenat T-080 4.5% by weight Ethylene glycol 10 % by weight Silicon SRE 0.5% by weight 13.5 g of Sapogenat T-080 emulsifier (ethoxylated tributyl phenol) melted at 80 C and 12 g of Tensiofix AS emulsifier (solution of calcium dodecyl benzene-sulfonate and ethoxylated nonyl phenol in n-butanol) homogenized and melted at a temperature not exceeding 60"C are added to a solution of 145 g cosmetical white oil heated to 605C in a Molines 075 laboratory pearl mill under stirring.To the tenzide oil mixture 30 g of ethylene glycol are added and the components are homogenized by stirring for 10 minutes. 98.1 g of compound No. 6 (previously finely ground in a mortar) are added to the liquid mixture. After stirring for 5 minutes (1500 r.p.m. in the presence of 350 g glass pearls, diameter 1 mm) grinding is continued for 2 hours, whereupon 1.5 g of Silicon SRE antifoam agent (30% emulsion of dimethyl silicon oil) are distributed in the oily suspension within 3 minutes under stirring.

Example 26 Dusting powder (DP) Compound No. 8 1.15% by weight Ultrasil VN 3 3 % by weight China-clay 15.85% by weight Talc 80 % by weight 9510 g of China-clay and 1800 g of Ultrasil VN3 (synthetic sodium-aluminium silicate) are admixed in a 50 1 band-mixer, whereupon 690 g of compound No. 8 (previously ground in a hammer-mill) are added and stirring is continued for 30 minutes. The active ingredient premix is ground in an Ultraplex 250 type mill (feeding rate 20 kg/h) to an extent that the amount of the fraction above 44 micrometers should not exceed 0.5%. After grinding the active ingredient premix is admixed with talc in a ratio of 1:4 in a L6dige 300 type jet mixer (stirring time 10 minutes).

Example 27 Emulsifiable concentrate (20 EC) Compound No. 12 20.4% by weight 2-ethoxy-ethanol 10 % by weight Cyclohexanone 35 % by weight Emulsogen EL 360 7 % by weight Tensiofix CD 5 3 % by weight Xylene 24.6% by weight Into a 500 1 emailled autoclave, equipped with a stirrer, 37 kg of 2-ethoxy-ethanol, 129.5 g of cyclohexanone and 91 kg of xylene are weighed in and in this solvent mixture 26 kg of Emulsogen EL 360 (ethoxylated castor oil) and 11.1 kg of Tensiofix CD 5) ethoxylated coccoalcohol) emulsifiers are dissolved. The emulsifiers are added in a melt form (60-70"C). Finally 75.5 kg of compound No. 12 are added, stirring is continued for 2 hours and a clear transparent solution is obtained.

Example 28 Emulsifiable concentrate (35 EC) Compound No. 15 35.7% by weight Cyclohexanone 10 % by weight Tensiofix CG 21 2 % by weight Tensiofix B 7453 8 % by weight Xylene 44.3% by weight 6 g of Tensiofix CG 21 emulsifier (a mixture of ethoxylated fatty alcohol, ethoxylated nonyl phenol and phosphates thereof) and 24 g of Tensiofix B 7453 emulsifier (a solution of calcium dodecyl benzenesulfonate, ethoxylated nonyl phenol and ethoxylated-propoxylated nonyl phenol, in n-butanol) are dissolved in a mixture of 30 g of cyclohexanone and 133 g of xylene, whereupon 107 g of compound No. 15 are added and dissolved in the liquid containing tensides.

Example 29 Herbicidal activity test The herbicidal activity of the new compounds of the present invention is tested by using various formulations and a maximum water-amount of 100 1/ha. The solutions and dilutions, respectively, corresponding to the desired doses and application rates are sprayed immediately after the preparation thereof onto the culturing vessels comprising the seeds and emerged plants. Pre-emergent treatment is carried out immediately after sowing of the seeds and spreading while post-emergent treatment is accomplished 10 days after emergence of the plants. The treated (sprayed) cultivating vessels are kept in a glass house at 20-25"C and the soil is irrigated as required. The rate of damage of the plants is assessed 3 weeks after pre-emergent treatment and 1 week after post-emergent treatment, respectively. The results are assessed with the aid of a scale between 0 and 10, wherein O=untreated control and 10=complete damage and killed plants.

The results are summarized in Table 2. In the heading the following abbreviations are used: =Sinapsis arvensis II =amaranthus retroflexus III = Setaria italica IV =Echinochloa crusgalli V = bean VI = soya VII =peanut VIII. =alfalfa IX =sunflower Table 2 Herbicidal activity and selectivity of the compounds Test compound Dose Plant and method of treatment No.

I II III IV V VI VII VIII IX A B A B A B A B A B A B A B A B A B 3 1 1 2 3 0 1 0 0 0 0 00 00 00 0 0 0 0 0 3 6 6 7 7 8 0 3 0 0 0 0 0 0 0 0 0 0 0 0 12 10 9 10 10 5 9 2 2 0 0 0 0 0 0 0 0 0 0 3 0 4 0 0 0 2 0 3 0 0 0 0 0 0 0 0 0 0 8 6 2 5 4 5 1 3 0 0 0 0 0 0 0 0 0 0 0 0 12 3 9 6 8 2 8 2 9 0 0 0 0 0 0 0 0 0 0 3 3 3 5 6 3 3 3 3 0 0 0 0 0 0 0 0 0 0 10 6 10 8 10 10 10 10 9 6 1 2 1 2 1 2 1 2 1 2 12 10 10 10 10 10 10 10 10 2 3 2 3 2 3 2 3 2 3 3 3 2 4 5 1 3 0 0 0 0 0 0 0 0 0 0 0 0 11 6 6 7 6 6 5 8 3 2 1 1 1 1 1 1 1 1 1 1 12 10 9 9 10 10 9 8 7 2 2 2 2 2 2 2 2 2 2 Table 2 Test compound Dose Plant and method of treatment No.

I II III IV V VI VII VIII IX A B A B A B A B A B A B A B A B A B 3 5 4 6 8 5 5 3 2 0 0 0 0 0 0 0 0 0 0 12 6 9 8 10 10 8 8 6 4 1 1 1 1 1 1 1 1 1 1 12 10 10 10 10 10 10 9 8 2 2 2 2 2 2 2 2 2 2 3 2 2 3 3 4 2 2 2 0 0 0 0 0 0 0 0 0 0 13 6 4 3 5 6 5 4 4 4 1 1 1 1 1 1 1 1 1 1 12 7 5 8 7 9 6 8 8 2 2 2 2 2 2 2 2 2 2 3 3 6 3 8 3 4 0 0 0 0 0 0 0 0 0 0 0 0 16 6 6 8 5 9 6 8 3 4 1 0 1 0 1 0 1 0 1 0 12 9 9 7 10 8 9 6 8 1 0 1 0 1 0 1 0 1 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 18 6 2 5 3 3 1 2 0 0 0 0 0 0 0 0 0 0 0 0 12 7 8 7 9 8 7.5 5 7 0 0 0 0 0 0 0 0 0 0 Fluorodifen 3 0 3 3 4 1 3 1 1 0 0 0 0 0 0 0 0 0 0 6 3 5 5 6 6 6 5 7 0 2 0 2 0 2 0 2 0 2 (standard) 12 9 8 7 8 9 9 7 8 2 3 2 3 2 3 2 3 2 3 It appears from Table 2 that compounds of the general Formula (I/b)

according to the invention possess outstanding herbicidal properties.It can be generally stated that the compounds of the general Formula (I) all exhibit herbicidal effect and the sub-group of the general Formula (I/b) exerts particularly valuable herbicidal effect.

On studying herbicidal activity it has been found that it is advisable to carry out herbicidal treatment at germination or at a cotyledonous or some-leafed stage of the weeds. The compositions can be applied after sowing and before emergence of the cultivated plant (pre-emergent treatment) or after emergence thereof (post-emergent treatment). Thus the compositions according to the present invention can be spread onto the surface of the soil to combat emerging weeds or can be applied onto the already emerged weeds. For the latter application-method compositions which can be applied without or with a small amount of water proved to be particularly suitable (e.g. LV or ULV type compositions).

The new herbicidal compounds of the present invention do not damage several cultivated plants i.e. are suitable for selective control of seeds in cultures of leguminous plants.

It has also been found that a part of the compounds of the present invention is active against fungal pests of cultivated plants (see Example 30).

Example 30 Fungicidal activity test -Agar plates are prepared by pouring into Petri-dishes a potato-starch nutrient medium comprising 2% of dextrose and allowing the medium to solifify.

-From the sprays of the test-compounds stock-solutions having a concentration of 2000, 200 and 20 ppm, respectively, are prepared.

-Spore-suspensions of the test fungi are prepared in such a dilution that on placing one drop of the spore suspension on a slide under a 100-160-fold magnifying, at an average of 5-10 visual fields, 25-30 spores should be visible on the visual field.

-1 ml of the ready-for-use spore suspension is added with the aid of a pipette to 1 ml of each of the dilution series of the test compound; thus a fungicidal active ingredient concentration of 1000, 100 and 10 ppm, respectively, is obtained. The solutions comprising the spore suspension are allowed to stand for 30 minutes whereupon the bottom of a sterile test tube is immersed into the mixture of the fungicide and the spore suspension, and with the bottom of the test tube a strip is drawn on the prepared agar-plate and thereafter the culture is inoculated.

After the fungi are well grown in the control-treatments, the evaluation is carried out by comparing the growth inhibition of the infected fungi colony to that of the control. The results are summarized in Table 3; as reference compound captan is used.

Table 3 Fungicidal activity Test com- Concentra- Fungicidal effect, in % against pound No. tion, ppm Aspergillus niger Fusarium oxysporum 8. 1000 65 100 100 35 75 10 5 15 11. 1000 100 100 100 80 95 10 40 50 12. 1000 100 100 100 95 100 10 45 50 18. 1000 90 95 100 70 80 10 40 20 Captan 1000 90 100 standard 100 65 80 10 35 30 The above data show that the compounds of the present invention possess very high fungicidal effect in addition to the herbicidal activity (with the exception of compound No. 16 which exhibits only herbicidal effect).

Claims (35)

1. Pesticidal composition comprising as active ingredient in an amount of 0.01-95% by weight at least one compound of the general Formula (I)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; Z stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl; R, stands for hydrogen or nitro and R2 represents C14 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stand for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogen in admixture with one or more solid and/or liquid carrier(s)-preferably ground natural minerals or inert organic solvents-and optionally with surfactant(s)-preferably anionic or nin-ionic emulsifying and/or dispersing agent(s).

2. Composition according to Claim 1 comprising as active ingredient at least one compound of the general Formula (I/a)

falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, W, V and R2 with the proviso are as stated in Claim 1).

3. Composition according to Claim 1 comprising as active ingredient at least one compound of the general Formula (I/b)

falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, V, W and R2 with the proviso are as stated in Claim 1).

4. Composition according to Claim 3 comprising as active ingredient at least one compound of the general Formula (I/b) falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, V and W with the proviso are as stated in Claim 1 and R2 stands for C14 alkyl).

5. Composition according to Claim 2 comprising as active ingredient 4-(3-[(2,6-dichloro-4- trifluoromethyl)-phenoxy]-benzylidene}-2-methyloxazoline-5-one.

6. Composition according to Claim 2 comprising as active ingredient 4-43-[(2,6-dichloro-4- trifluoromethyl)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one .

7. Composition according to Claim 3 comprising as active ingredient 4-(5-[(2-chloro-4-trifluo- romethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5-one .

8. Composition according to any of Claim 3 or 4 comprising as active ingredient 4-(5-[(2,6- dichloro-4-trifluoromethyl)-phenoxy]-2-nitrobenzylidenei-2-methyl-oxazoline-5-one.

9. Composition according to Claim 3 or 4 comprising as active ingredient 4--i5-[(2-chloro-4- trifluornmethyl)-phenoxy]-2-nitro-benzylidene-2-ethyl-oxazoline-5-one.

10. Composition according to Claim 3 comprising as active ingredient 4-(5-[(2-chloro-4-trifluo- romethyl)-phenoxy]-2-nitro-benzylidenet-2-phenyl-oxazoline-5-one .

11. Composition according to Claim 3 comprising as active ingredient 4-(5-[(2,6-dichloro-4- trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-phenyl-oxazoline-5-one.

12. Process for the preparation of new compounds of the general Formula (i)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl; R, stands for hydrogen or nitro and R2 represents C, 4 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stand for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogenwhich comprises reacting a compound of the general Formula (II)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands four hydrogen, chlorine, nitro or trifluoromethyl; R, stands for hydrogen or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stant for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogen with a N-acyl-glycine of the general Formula (III)

wherein Ac stands for C25 acyl, benzoyl, chlorobenzoyl or nitrobenzoyl-in the presence of an acetate-preferably anhydrous sodium acetate-and a carboxylic acid anhydride-preferably acetic anhydride-at a temperature between 40"C and the boiling point of the reaction mixture, whereby the N-acyl-glycine of the general Formula (III) is used in an excess of 0-1 mole, and isolating the product thus obtained from the reaction mixture in a known manner.

13. Process according to Claim 12 which comprises using the acetate-preferably anhydrous sodium acetate-in an amount of 0.5-1.5 moles reiated to 1 mole of the compound of the general Formula (II).

14. Process according to any of Claim 12 or 13 which comprises using the carboxylic acid anhydride-preferably acetic anhydride-in an amount of 1-10 mole(s)-preferably 2-7 moles-related to 1 mole of the compound of the general Formula (II).

15. Process according to any of Claims 12-14 which comprises carrying out the reaction at a temperature between 80"C and 120 C for a period between 30 minutes and 3 hours.

16. Process according to any of Claims 12-15 which comprises preparing the N-acyl-glycine of the general Formula (Ill)--wherein Ac is as stated in Claim 12-in situ in the reaction mixture.

17. Compounds of the general Formula (I)

wherein X stands for hydrogen, chlorine, nitro or trifluoromethyl; Y stands for hydrogen or chlorine; Z stands for hydrogen, chlorine, nitro or trifluoromethyl; V stands for hydrogen, chlorine or nitro; W stands for hydrogen, chlorine, nitro or trifluoromethyl; R, stands for hydrogen or nitro and R2 represents C14 alkyl, phenyl or phenyl substituted by chlorine or nitro; with the proviso that from the substituents X, Y, Z, V and W (a) only one can stand for trifluoromethyl; and (b) from the substituents other than hydrogen or trifluoromethyl not more than two can be identical and (c) not more than four can stand for hydrogen.

18. Compounds of the general Formula (I/a) falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, V, W and R2 are as stated in Claim 17).

19. Compounds of the general Formula (I/b) falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, V, W and R2 are as stated in Claim 17).

20. Compounds of the general Formula (I/b) falling under the scope of the compounds of the general Formula (I) (wherein X, Y, Z, V and W are as stated in Claim 17 and R2 stands for C14 alkyl).

21. 4-43-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzylidenet-2-methyl-oxazoline-5-one.

22. 4-{3-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-benzylidene}-2-phenyl-oxazoline-5-one.

23. 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5-one.

24. 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-methyl-oxazoline-5- one.

25. 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-ethyl-oxazoline-5-one.

26. 4-{5-[(2-chloro-4-trifluoromethyl)-phenoxy]-2-nitro-benzylidene}-2-phenyl-oxazoline-5-one.

27. 4-{5-[(2,6-dichloro-4-trifluoromethyl)-phenoxa]-2-nitro-benzylidene}-2-phenyl-oxazoline-5one.

28. Process for the preparation of pesticidal compositions according to Claim 1 which comprises admixing a compound of the general Formula (I) as active ingredient with suitable inert solid or liquid carriers and optionally with auxiliary agents.

29. Method for combating pests--particularly weeds and/or fungal pests-which comprises applying onto the pests or the objects to be protected or into the environment thereof an effective amount of a compound of the general Formula (I) or a pesticidal composition comprising the same.

30. Compounds of the general Formula (I) whenever prepared according to the process claimed in any of Claims 12-16.

31. Pesticial composition substantially as hereinbefore described in any one of Examples 19 to 28.

32. A process of making pesticidal compositions substantially as herein before described in any one of Examples 19 to 28.

33. Compounds 1 to 18 as hereinbefore described.

34. A process of making compounds claimed in claim 17, which process is substantially as hereinbefore described in any one of Examples 1 to 18.

35. A process of combating pests as claimed in claim 29 which process is substantially as hereinbefore described in Example 29 or Example 30.