# Patent

## Title
Herbicidal sulfonamides

## Abstract

This is a divisional of application Ser. No. 699,388 filed on Feb. 7, 1985, now U.S. Pat. No. 4,685,961.

## Background
The present invention relates to novel substituted N-sulfonyl-N'-pyrimidinylureas and N-sulfonyl-N'-triazinylureas and salts thereof with herbicidal and plant growth regulating properties, to the preparation thereof, to compositions containing them and to the use thereof for controlling weeds, in particular selectively, in crops of useful plants, or for regulating and inhibiting plant growth. The invention further relates to novel pyrimidin-2-ylureas and triazi-n-ylalkylamines prepared as intermediates.

The substituted N-sulfonyl-N'pyrimidinylureas and N-sulfonyl-N'-triazinylureas of this invention have the formula I ##STR3## wherein E is nitrogen or --CH.dbd., ##STR4## Y is oxygen or an S(O).sub.m radical, m is O or an integer from 1 to 2, -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, an amino group NR.sup.10 R.sup.11, a ketal radical --CR.sup.7 (OC.sub.1 -C.sub.7 alkyl).sub.2 or ##STR5## a tetrahydrofuran-2-yloxy or tetrahydropyran-2-yloxy radical, --OSO.sub.2 R.sup.8, --COR.sup.8, ##STR6## --SO.sub.2 NR.sup.10 R.sup.11, SO.sub.2 R.sup.8, YR.sup.8, phenyl, benzyl or phenoxy, wherein the phenyl nucleus can be substituted by one or more identical or different members selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy, alkoxy, C.sub.1 -C.sub.4 haloalkyl or nitro, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkoxyalkoxy, cyclopropyl, NH.sub.2, C.sub.1 -C.sub.4 alkylamino, di(C.sub.1 -C.sub.4)alkylamino or a 5- to 7-membered nitrogen-containing heterocycle which is bound through the nitrogen atom and which may contain a further hetero atom, or are a --CH(OCH.sub.3).sub.2 or ##STR7## radical, R.sup.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or a phenyl, benzyl, furyl, thienyl or naphthyl radical, each of which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy, heterocyclic radical which is bound through a nitrogen atom and may contain further hetero atoms in the ring and may be fused to a benzene ring and is unsubstituted or substituted by one or more identical or different members selected from the group consisting of nitro, halogen or C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.6 cycloalky, C.sub.4 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 cyanoalkyl, C.sub.1 -C.sub.4 alkyl-NR.sup.9 R.sup.10, benzyl or benzyl which is substituted by halogen, is not hydrogen, halogen, C.sub.2 -C.sub.4 alkoxy, carboxyl, C.sub.1 -C.sub.4 alkoxycarbonyl or --CONR.sup.10 R.sup.11, or is a phenyl, benzyl or naphthyl radical, each of which can be substituted by one or more identical or different members selected from the group consisting of halogen, nitro, carboxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy, and in an --SR.sup.9 radical R.sup.9 can also be a radical selected from --CZ--C.sub.1 -C.sub.4 alkyl, --CZO--C.sub.1 -C.sub.4 alkyl, --CZNR.sup.10 R.sup.11, --CZ-phenyl, CZ-benzyl or CZ-naphthyl, wherein the phenyl rings may be substituted as indicated above, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 cyanoalkyl, or one of R.sup.10  and R.sup.11 may also be C.sub.1 -C.sub.4 alkoxy or C.sub.2 -C.sub.4 alkoxyalkyl, phenyl or benzyl, and the phenyl ring may be substituted by one or identical or different members selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy; or R.sup.10 and R.sup.11, together with the nitrogen atom to which they are attached, may also be a 5- to 7-membered saturated or partially saturated heterocycle which may contain a further nitrogen or sulfur atom in the ring and/or one or two further nitrogen atoms, and which may be substituted by halogen and/or C.sub.1 -C.sub.4 alkyl.

The invention also relates to the salts of these sulfonylureas with organic and inorganic bases.

Herbicidal ureas, triazines and pyrimidines are generally known in the art. Sulfonylureas with herbicidal and plant growth regulating properties have recently been described for example in European patent applications Nos. 44211, 44807 and 44808, and also in UK patent applications Nos. 2 112 783 and 2 112 784.

Alkyl in the above definitions denotes straight chain or branched alkyl, for example methyl, ethyl, n-propyl, isopropyl or the 4 isomers of butyl.

Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, the 4 isomers of butoxy, n-amyloxy, isoamyloxy, 2-amyloxy or 3-amyloxy, with methoxy, ethoxy or isopropoxy being preferred.

Halogen by itself or as moiety of haloalkoxy, haloalkyl or haloalkylthio denotes fluorine, chlorine and bromine, with fluorine and chlorine being preferred.

Within the scope of this invention, the radicals defined for R.sup.6 comprise for example the following radicals: --S--C.sub.1 -C.sub.4 alkyl --S--CH.sub.2 COOC.sub.1 -C.sub.4 alkyl phenylthio  --SCH.sub.2 COOH --SO--C.sub.1 -C.sub.4 alkyl --S--CH.sub.2 CONHC.sub.1 -C.sub.4 alkyl benzylthio  --SCH(CH.sub.3)COOH --SO.sub.2 C.sub.1 -C.sub.4 alkyl --S--CH.sub.2 CON(C.sub.1 -C.sub.4 alkyl).sub.2 benzoylthio --S--CO--C.sub.1 -C.sub.4 alkyl --S--CS--OC.sub.1 -C.sub.4 alkyl --SCSN(C.sub.1 -C.sub.4 alkyl).sub.2 __________________________________________________________________________

as well as the following heterocyclic amino radicals: 1,2,4-triazolyl, 1,2,3,4-tetrazol-1-yl, pyrazol-1-yl, imidazol-1-yl, benztriazol-1-yl, benzimidazol-1-yl, indol-1-yl, indadzol-1-yl, pyrimidin-1-yl, pyridazin-1-yl, pyrazin-1-yl, which rings may be substituted by one to three members selected from nitro, halogen, preferably chlorine or bromine, and/or C.sub.1 -C.sub.4 alkyl, preferably methyl.

The 5- to 7-membered saturated or partially saturated heterocyclic radicals falling within the definition of the amino radical NR.sup.10 R.sup.11 comprise for example the following radicals: pyrrolidino, piperidino, morpholino, thiomorpholino, azepino, imidazol-1-yl, triazol-1-yl, 1,3-oxazol-3-yl, 1,3-thiazol-1-yl, piperazin-1-yl, which radicals may be unsubstituted or substituted by halogen, preferably chlorine or bromine and/or by C.sub.1 -C.sub.4 alkyl, preferably methyl.

Alkoxyalkyl radicals are methoxymethyl, ethoxymethyl, methoxyethyl and ethoxyethyl, with methoxyethyl being preferred. Within the scope of this invention, alkoxyalkyl radicals are methoxymethoxy, ethoxymethoxy, methoxyethoxy and ethoxyethoxy. Haloalkyl by itself or as moiety of another substituent such as haloalkoxy or haloalkylthio is usually chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1-dichloroethyl, pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl, and 1,1,2,3,3,3-hexafluoropropyl. Fluoromethyl, chloromethyl, difluoromethyl and trifluoromethyl are preferred.

Preferred compounds of formula I are those wherein either ##STR8## radical is a phenyl radical which is substituted in the ortho-position by R.sup.1, nitrogen atom and may contain further hetero atoms in the ring, and may be fused to a benzene ring and may be unsusbstituted or substituted by one or more members selected from the group consisting of nitro, halogen and/or C.sub.1 -C.sub.4 alkyl.

Preferred compounds are for example those of the formula Ic ##STR9## wherein E, R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are as defined for formula I; and those of the general formula Id ##STR10## wherein E, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.8 are as defined for formula I.

The compounds of formula I are prepared for example by the following methods.

A first process comprises reacting a sulfonyl isocyanate of formula II ##STR11## wherein R.sup.1, R.sup.2, X and Z are as defined for formula I, with the equivalent amount of a 2-aminopyrimidine or 2-aminotriazine of formula III ##STR12## wherein E, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined for formula I, in an inert organic solvent or diluent, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

A second process for obtaining the compounds of formula I comprises reacting a sulfonylamide of formula IV ##STR13## wherein R.sup.1, R.sup.2 and X are as defined for formula I, with the equivalent amount of a 2-pyrimidinyl- or 2-triazinylcarbamoylhalide of formula V ##STR14## wherein Hal is a halogen atom, preferably chlorine or bromine, and E, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and Z are as defined for formula I, in an inert solvent or diluent and in the presence of a base, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

A third process for obtaining the compounds of formula I comprises reacting a sulfonylurea of formula VI ##STR15## wherein E, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and Z are as defined for formula I, with the equivalent amount of a methyl halide of formula VII ##STR16## wherein Hal is a halogen atom, preferably a chlorine or bromine atom, and R.sup.5 and R.sup.6 are as defined for formula I, in an inert solvent or diluent and in the presence of a base, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

If desired, the ureas of formula I can be converted into basic addition salts with amines, alkali metal hydroxides or alkaline earth metal hydroxides or with quaternary ammonium bases. This is done for example by reacting the urea with the equimolar amount of base and removing the solvent by evaporation. Such reactions are known and are described for example in U.S. Pat. Nos. 2,834,757 and 3,410,887.

It is convenient to carry out these reactions for obtaining compounds of formula I in aprotic, inert organic solvents.

Examples of such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane; chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, or chlorobenzene; ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxan; nitriles such as acetonitrile or propionitrile; amides such as dimethylformamide, diethylformamide or N-methylpyrrolidinone.

The reaction temperatures are preferably in the range from -20.degree. to +120.degree. C. The coupling reactions are normally slightly exothermic and can be carried out at room temperature. To shorten the reaction time or also to initiate the reaction it is expedient to heat the reaction mixture briefly to boiling point. The reaction times can also be shortened by addition of a few drops of a base or isocyanate as catalyst. Preferred bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]-non-5-ene or 1,8-diazabicyclo[5,4,0]undec-7-ene. However, the bases employed may also be inorganic bases, e.g. hydrides such as sodium hydride or calcium hydride, hydroxides such as sodium hydroxide or potassium hydroxide, carbonates such as sodium or potassium carbonate, or bicarbonates such as potassium or sodium bicarbonate.

The final products of formula I can be isolated by concentrating the reaction mixture and/or removing the solvent by evaporation, and by recrystallisation or by triturating the solid residue in a solvent in which it is poorly soluble, such as an ether, an aromatic hydrocarbon or a chlorinated hydrocarbon.

In addition to these general methods of preparing the compounds of formula I, and depending on the meanings of the substituents R.sup.5 and R.sup.6, further synthesis paths, each of which is suitable only for one specific group of final products, are also possible. Such syntheses are illustrated in the following schemes. In the formulae below, E, m, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, X and Z are as defined for formula I. The Roman numerals I, II and IV denote the formulae so numbered above.

Scheme 1 ##STR17##

A 2-aminopyridine or a 2-amino-1,3,5-triazine of formula VIII is condensed with an aldehyde to give the Schiff's base, which is reacted in situ with the mercapto compound. The reaction is carried out at elevated temperature, for example at the boiliong point of the reaction mixture in an organic solvent or mixture of solvents, e.g. an alkanol and/or an aromatic hydrocarbon. A small amount of catalyst is added to accelerate the reaction. Example 1 describes the preparation of a compound of the formula IIIa and further compounds are listed in Table 1. These intermediates are novel and constitute an object of the invention. The condensates of formula IIIa are then reacted, in accordance with the first preparatory process, with a sulfonyl isocyanate of formula II, as described in Examples 9-11.

Scheme 2 ##STR18##

In this process also the 2-aminopyridine or 2-aminotriazine of formula VIII is reacted with a cyclic secondary amine. The reaction is conducted in the presence of a small amount of acid in an organic solovent. Examples 5-8 describe such reactions to give compounds of the formula IIIb. These compounds can then be further reacted with a sulfonyl isocyanate of formula II to give an urea of formula I, as described in Examples 12 and 13.

Scheme 3 ##STR19##

The 2-aminopyrimidine or 2-aminotriazine of formula VIII and a sulfinic acid are charged to an organic solvent or diluent and the mixture is heated to give the aldehyde. The condensate can be precipitated by diluting the reaction mixture with water. Such a reaction is described in Example 2. Further compounds are listed in Table 2. The intermediates of formula IIIc likewise constitute an object of this invention. The further reaction of the compound of formula IIIc with a sulfonyl isocyanate of formula II to give the urea of formula I is performed in known manner.

A compound of formula IIIa can also be converted by oxidation into a compound of formula IIIc ##STR20## wherein n is 1 or 2.

The oxidation is carried out in an inert solvent or diluent in the temperature range from 0.degree. C. to the boiling point of the reaction mixture. Suitable oxidising agents are hydrogen peroxide, an organic peracid such as perbenzoic acid or peracetic acid, or also potassium permanganate or chromium oxide. The duration of the oxidation and the amount of oxidising agent to be used depend on the desired oxidation step of the compound of formula IIIa.

Scheme 4 ##STR21##

This scheme corresponds more or less to the above described second process for the preparation of the sulfonylureas of formula I, except that first a (2-pyrimidinyl)-N-methylcarbamoyl halide or N-(2-triazinyl)-N-methylcarbamoyl halide of the formula Va is prepared in a preliminary step, in an inert organic solvent, by condensing the compound of formula III with a carbonyl dihalide (phosgene), and then reacting the compound of formula Va with the sulfonamide of formula IV to give an urea of formula I.

Scheme 5 ##STR22##

A sulfonyl halide of formula IV is reacted with a methyl halide, in an inert organic solvent and in the presence of a base, to give an urea of formula I. The reaction takes place at room temperature and can be speeded up by heating briefly to the boiling point of the reaction mixture.

Scheme 6 ##STR23##

This scheme is the same as scheme 1, except that a sulfonylurea of formula XI is used as starting material. This sulfonylurea is then reacted with an aldehyde and a mercaptan in an inert organic solvent or diluent and in the presence of a small amount of acid. The resultant sulfonylurea of formula Ia can be oxidised to give the corresponding sulfinyl or sulfonyl compound of formula Ib by an oxidation similar to that described after scheme III. ##STR24##

Scheme 7 ##STR25##

This scheme is similar to scheme 2, except that the starting material employed is a sulfonylurea of formula IX, which is then reacted, in an inert solvent or diluent, with an aldehyde and a cyclic secondary amine, in the presence of a small amount of acid and at elevated temperature, to give an sulfonylurea of formula I.

The final products can be isolated by concentrating the reaction mixture and/or evaporating off the solvent, and purified by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, e.g. in an ether, an aromatic hydrocarbon or a chlorinated hydrocarbon.

The compounds of formula I are stable compounds, and no protective measures are required for handling them.

When used at low rates of application, the compounds of formula I have good selective growth inhibiting and selective herbicidal properties which make them most suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, maize and rice. In some cases damage is also caused to weeds which have only been controlled up to now with total herbicides.

The mode of action of these compounds is unusual. Many are translocatable, i.e. they are absorbed by the plant and transported to other parts of it where they then exert their action. Thus, for example, it is possible to damage perennial weeds to the roots by surface treatment. Compared with other herbicides and growth regulators, the novel compounds of the formula I are effective even when used at very low rates of application.

The compounds of formula I have in addition pronounced growth-regulating, especially growth-inhibiting, properties. The growth of both monocots and dicots is inhibited. Thus, for example, the compounds of formula I selectively inhibit the growth of leguminosae which are frequently planted as cover crops in tropical regions, so that, while soil erosion between cultivated plants is prevented, the cover crops cannot compete with the cultivated plants.

Inhibition of the vegetative growth of many cultivated plants permits more plants to be sown in a crop area, so that a higher yield may be obtained per unit of area. A further mechanism of yield increase using growth regulators resides in the fact that nutrients are able increasingly to promote flower formation and fruiting, whilst vegetative growth is inhibited.

At higher rates of application, all tested plants are so severely damaged in their development that they die.

The invention also relates to herbicidal and growth-regulating compositions which contain a novel compound of the formula I, and also to methods of controlling weeds pre- and postemergence and of inhibiting the growth of monocots and dicots, especially grasses, tropical cover crops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation, and are therefore formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations in e.g. polymer substances. As with the nature of the compositions, the methods of applications, such as spraying, atomising, dusting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions containing the compound (active ingredient) of the formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, as well as epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.

Depending on the nature of the compound of the formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts or higher fatty acids (C.sub.10 -C.sub.22), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurin salts.

More frequently, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a C.sub.8 -C.sub.22 alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethylanolamine salts of dodecylbenzene sulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30  glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediamine propylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan and polyoxyethylene sorbitan trioleate are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C.sub.8 -C.sub.22 alkyl radical and, as further substituents, lower unsubstituted or halogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation are described e.g. in the following publications: "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., 1981; H. Stache, "Tensid-Taschenbuch", 2nd Edition, C. Hanser Verlag, Munich & Vienna, 1981; M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81.

The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1 to 80%, of a compound of the formula I, 1 to 99.9%, of a solid or liquid adjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the following constituents (%=percentage by weight):

Emulsifiable concentrates active ingredient: 1 to 20%, preferably 5 to 10% surfactant:   5 to 30%, preferably 10 to 20% liquid carrier: 50 to 94%, preferably 70 to 85% ______________________________________

Dusts active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99% ______________________________________

Suspension concentrates active ingredient: 5 to 75%, preferably 10 to 50% water:        94 to 25%, preferably 90 to 30% surfactant:   1 to 40%, preferably 2 to 30% ______________________________________

Wettable powders active ingredient: 0.5 to 90%, preferably 1 to 80% surfactant:   0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 95%, preferably 15 to 90% ______________________________________

Granulates active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%. ______________________________________

Whereas commercial products will be preferably formulated as concentrates, the end user will normally employ dilute formulations. The formulations can be diluted to a concentration as low as 0.001% The rates of application are normally from 0.01 to 10 kg a.i./ha, preferably from 0.025 to 5 kg a.i./ha.

The compositions may also contain further ingredients such as stabilisers, antifoams, viscosity regulators, binders, tackifiers, as well as fertilisers and other compounds for obtaining special effects.

The invention is illustrated by the following Examples. 2-[(4-chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine (intermediate) ##STR26##

A mixture of 13.99 g of 2-amino-4-methoxy-6-methylpyrimidine (0.1 mole), 14.8 g of 4-chlorothiophenol (0.1 mole), 9.4 g of aqueous 35% formaldehyde (0.11 mole) and 1 g of acetic acid are heated under reflux for 1 hour in 100 ml of methanol. The resultant solution is clarified by filtration, diluted with 150 ml of toluene and then the solvent is removed in a rotary evaporator. The residue crystallises after standing for some time. The melting point is 78.degree.-82.degree. after recrystallisation from hexane. The yield is 24 g (81% of theory).

The following compounds are prepared in accordance with this Example: __________________________________________________________________________ ##STR27##                              (IIIa) No. R.sup.3 R.sup.4 R.sup.5 E  R.sup.8    m.p. (.degree.C.) __________________________________________________________________________ 1.01 CH.sub.3 CH.sub.3 H       CH 4-chlorophenyl 110-113.degree. 1.02 OCH.sub.3 CH.sub.3 H       CH 4-chlorophenyl 78-82.degree. 1.03 Cl  OCH.sub.3 H       CH 4-chlorophenyl 102-105.degree. 1.04 OCH.sub.3 OCH.sub.3 H       CH 4-chlorophenyl 112-114.degree. 1.05 CH.sub.3 CH.sub.3 H       CH 4-fluorophenyl 96-98.degree. 1.06 OCH.sub.3 CH.sub.3 H       CH 2,4,5-trichlorophenyl 117-119.degree. 1.07 OCH.sub.3 CH.sub.3 H       CH 4-acetylaminophenyl 182-183.degree. 1.08 CH.sub.3 CH.sub.3 H       CH .beta.-naphthyl 115-118.degree. 1.09 OCH.sub.3 CH.sub.3 H       CH .beta.-naphthyl 101-102.degree. 1.10 CH.sub.3 CH.sub.3 H       CH carbanilidomethyl 128-130.degree. 1.11 Cl  OCH.sub. 3 H       CH p-tolyl    106-109.degree. 1.12 CH.sub.3 CH.sub.3 H       CH CH.sub.2COOH 123-125.degree. (dec.) 1.13 CH.sub.3 OCH.sub.3 H       CH CH.sub.2COOH 160-164.degree. 1.14 CH.sub.3 CH.sub.3 H       CH CH(CH.sub.3)COOH 141-145.degree. 1.15 CH.sub.3 CH.sub.3 H       CH CH.sub.2 CH.sub.2COOH 150-153.degree. 1.16 CH.sub.3 CH.sub.3 H       CH CH.sub.2COOCH.sub.3 71-73.degree. 1.17 CH.sub.3 OCH.sub.3 H       CH CH.sub.2COOCH.sub.3 85-87.degree. 1.18 CH.sub.3 OCH.sub.3 H       CH Nphenylcarbamoyl- 161-163.degree. methyl 1.19 OCH.sub.3 OCH.sub.3 H       CH 4-tolyl     84-91.degree. 1.20 OCH.sub.3 CH.sub.2OCH.sub.3 H       CH 2,4,5-trichlorophenyl 124-126.degree. 1.21 CH.sub.3 CH.sub.3 CH.sub.3 CH 2-carboxylphenyl 162-163.degree. 1.22 CH.sub.3 CH.sub.3 C.sub.3 H.sub.7 (i) CH 2-carboxylphenyl 138-141.degree. 1.23 CH.sub.3 CH.sub.3 CH.sub.2Cl CH 2-carboxylphenyl 220-222.degree. (dec.) 1.24 CH.sub.3 CH.sub.3 COOH    CH 2-carboxylphenyl 180-182.degree. (dec.) 1.25 CH.sub.3 CH.sub. 3 2-Furyl CH 2-carboxylphenyl 169-171.degree. (dec.) 1.26 CH.sub.3 CH.sub.3 4-Chlorphenyl CH 2-carboxylphenyl 193-195.degree. (dec.) 1.27 CH.sub.3 CH.sub.3 H       CH 2-carboxylphenyl 226-228.degree. (dec.) __________________________________________________________________________ 4-dimethylamino-6-methoxy-2-(4-tolylsulfonyl)methylamino-1,3,5-triazine ##STR28##

8.5 g (0.05 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine and 9.1 g (0.05 mole) of toluene-5-sulfinic acid, sodium salt, are suspended in 100 ml of methanol and to the stirred suspension are added, in succession, 4.8 g (0.05 mole) of methanesulfonic acid and 4.7 g (0.055 mole) of aqueous 35% formaldehyde. The batch is then stirred for 30 minutes at room temperature and then for another 90 minutes under reflux. After cooling, the mixture is diluted with 1 liter of water and the crystalline precipitate is filtered with suction and dried. Melting point: 188.degree.-190.degree. C. Yield: 10 g (59% of theory). ##STR29##

12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine are suspended in 200 ml of water and then 9.7 g (0.1 mole) of methanesulfonic acid are stirred in to form a solution. To the stirred solution are added, in succession, 18.22 g (0.1 mole) of toluene-3-sulfonic acid, sodium salt, and 9.4 g (0.11 mole) of aqueous 35% formaldehyde. The mixture is stirred for 2 hours at room temperature and for another 30 minutes at 90.degree. C. The colourless precipitate is filtered with suction after cooling and dried. Melting point: 191.degree.-194.degree. C. Yield: 25 g (86% of theory).

The following compounds are obtained in accordance with Examples 2 and 3: __________________________________________________________________________ ##STR30##                              (IIIc) No. R.sup.3 R.sup.4 R.sup.5 m E  R.sup.9      m.p. (.degree.C.) __________________________________________________________________________ 2.01 CH.sub.3 CH.sub.3 H   2 CH CH.sub.3     145-148 2.02 CH.sub.3 CH.sub.3 H   2 CH p-tolyl      191-194.degree. 2.03 OCH.sub.3 CH.sub.3 H   2 CH p-tolyl      136-138.degree. 2.04 OCHF.sub.2 CH.sub.3 H   2 CH p-tolyl      165-166.degree. 2.05 N(CH.sub.3).sub.2 OCH.sub.3 H   2 N  p-tolyl      188-190.degree. 2.06 OCH.sub.3 OCH.sub.3 H   2 CH p-tolyl      135-140.degree. 2.07 OCH.sub.3 CH.sub.2 COH.sub.3 H   2 CH p-tolyl      142-144.degree. 2.08 Cl   OCH.sub.3 H   2 CH p-tolyl 2.09 Cl   CH.sub.3 H   2 CH p-tolyl 2.10 CH.sub.3 CH.sub.3 H   2 CH 4-chlorophenyl 178-180.degree. 2.11 OCH.sub.3 CH.sub.3 H   2 CH 4-chlorophenyl 2.12 CH.sub.3 CH.sub.3 H   2 CH 4-bromophenyl 184-186.degree. 2.13 CH.sub.3 OCH.sub.3 H   2 CH CH.sub.3     149-150.degree. 2.14 CH.sub.3 CH.sub.3 H   2 CH benzyl       154-159.degree. 2.15 CH.sub.3 OCH.sub.3 H   2 CH .beta.-naphthyl 167-169.degree. 2.16 CH.sub.3 CH.sub.3 CH.sub.3 2 CH p-tolyl      125-127.degree. 2.17 CH.sub.3 CH.sub.3 C.sub.3 H.sub.7 i 2 CH p-tolyl      116-118.degree. 2.18 OCH.sub.3 OCH.sub.3 H   2 CH CH.sub.3     149-151.degree. 2.19 OCH.sub.3 OCH.sub.3 H   2 CH C.sub.2 H.sub.5 145-147.degree. 2.20 OCH.sub.3 OCH.sub.3 H   2 CH n-C.sub.3 H.sub.7 117-120.degree. 2.21 OCH.sub.3 OCH.sub.3 H   2 CH benzyl       138-139.degree. 2.22 OCH.sub.3 OCH.sub.3 H   2 CH 2-methoxycarbonylbenzyl 135-136.degree. 2.23 OCH.sub.3 OCH.sub.3 H   2 CH phenyl       135-139.degree. 2.24 OCH.sub.3 OCH.sub.3 H   2 CH 2-difluoromethoxyphenyl 137-138.degree. 2.25 OCH.sub.3 OCH.sub.3 H   2 CH 2,4,6-trimethylphenyl 131-133.degree. 2.26 OCH.sub.3 OCH.sub.3 H   2 CH 4-bromophenyl 137-138.degree. 2.27 OCH.sub.3 OCH.sub.3 H   2 CH 4-chlorophenyl 140-141.degree. 2.28 OCH.sub.3 OCH.sub.3 H   2 CH .beta.-naphthyl 139-140.degree. 2.29 OCHF.sub.2 CH.sub.3 H   2 CH CH.sub.3     162-163.degree. (dec.) 2.30 N(CH.sub.3).sub.2 OCH.sub.3 H   2 CH CH.sub.3     184-187.degree. (dec.) __________________________________________________________________________ 4,6-dimethyl-2-(morpholin-4-ylthiocarbonylthiomethylamino)pyrimidine ##STR31##

6.6 g (0.1 mole) of 85% potassium hydroxide and 8.9 g (0.1 mole) of morpholine are dissolved in 200 ml of water and, with cooling, 7.7 g (0.1 mole) of carbon disulfide are added. The mixture is stirred until a yellowish homogeneous solution is obtained. With cooling and stirring, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and a solution of 12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine and 9.7 g (0.1 mole) of methanesulfonic acid in 50 ml of water are added in succession. The reaction mixture is further stirred at room temperature, whereupon first an oil precipitates, which crystallises after a short time. After 24 hours the batch is diluted with 1 liter of water and the crystalline precipitate is filtered with suction and dried, affording 24 g (80% of theory) of the title compound with a melting point of 119.degree.-121.degree. C.

The following compounds are prepared in accordance with Example 4: ______________________________________ ##STR32## m.p. No.  R.sup.3  R.sup.4 E    R.sup.9      (.degree.C.) ______________________________________ 3.01 CH.sub.3 CH.sub.3 CH   pyrrolidinothio- 116-118.degree. carbonyl 3.02 CH.sub.3 CH.sub.3 CH   morpholinothio- 119-121.degree. carbonyl 3.03 Cl       OCH.sub.3 CH   pyrrolidinothio- 136-139.degree. carbonyl 3.04 CH.sub.3 CH.sub.3 CH   azepinylthiocarbonyl 90-92.degree. 3.05 CH.sub.3 CH.sub.3 CH   methoxythiocarbonyl 3.06 CH.sub.3 CH.sub.3 CH   dimethylthiocarbamoyl 105-115.degree. 3.07 CH.sub.3 CH.sub.3 CH   acetyl 3.08 CH.sub.3 CH.sub.3 CH   benzoyl      >110.degree. (dec.) 3.09 OCHF.sub.2 CH.sub.3 CH   benzoyl      125-128.degree. (dec.) 3.10 CH.sub.3 OCH.sub.3 CH   benzoyl      107-109.degree. ______________________________________ 4-methoxy-6-methyl-2-(1,2,4-triazol-1-ylmethylamino)pyrimidine ##STR33##

With stirring, a mixture of 13.9 g (0.1 mole) of 2-amino-4-methoxy-6-methylpyrimidine, 7 g (0.1 mole) of 1,2,4-triazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of methanol is refluxed for 11/2 hours. First a clear solution forms, from which the reaction product precipitates in crystalline form after a time. After the reaction mixture has cooled, the crystalline title compound is filtered with suction and dried. Yield: 14 g. Melting point: 191.degree.-193.degree. C. 2-[(2,6-dichlorophenyl)-(1,2,4-triazol-1-yl)methyl]-amino-4,6-dimethylpyri midine ##STR34##

With stirring, a mixture of 6.3 g (0.05 mole) of 2-amino-4,6-dimethylpyrimidine, 8.8 g (0.05 mole) of 2,6-dichlorobenzaldehyde, 3.5 g (0.105 mole) of 1,2,4-triazole and 1 g of acetic acid in 50 ml of methanol is heated under reflux for 2 hours. The resultant clear yellowish solution is concentrated in a rotary evaporator and the residue is crystallised from methanol, affording 6 g (34% of theory) of the title compound, which undergoes conversion at 140.degree.-145.degree. C. and then melts at 158.degree.-159.degree. C. 2-(benztriazol-1-ylmethylamino)-4-dimethylamino-6-methoxy-1,3,5-triazine ##STR35##

With stirring, a mixture of 16.9 g (0.1 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine, 12 g (0.1 mole) of benztriazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of ethanol is heated under reflux for 2 hours. The still hot solution is clarified by filtration and crystals of the title compound precipitate from the cooled solution. The precipitate is filtered with suction and dried, affording 25 g (83% of theory) of crystalline product with a melting point of 222.degree.-224.degree. C. 4,6-dimethyl-2-[2-methylbenzimidizol-1-yl)methylamino]pyrimidine ##STR36##

With stirring, a mixture of 6.3 g (0.05 mole) of 2-amino-4,6-di-methylpyrimidne, 6.7 g (0.05 mole), 4.7 g (0.0055 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 50 ml of methanol is heated under reflux for 11/2 hours. To the resultant colourless solution are added 150 ml of toluene and the solvent is then removed in a rotary evaporator. The precipitated crystalline residue is recrystallised from ethyl acetate/methanol, affording 10 g (70% of theory) of the title compound which melts at 207.degree.-212.degree. C.

The following compounds are obtained by procedures analogous to those described in Examples 5 to 8: __________________________________________________________________________ ##STR37## No. R.sup.3 R.sup.4 R.sup.5 E  R.sup.9      m.p. (.degree.C.) __________________________________________________________________________ 4.01 CH.sub.3 CH.sub.3 H  CH 1,2,4-triazol 1-yl 162-164.degree. 4.02 OCH.sub.3 CH.sub.3 H  CH 1,2,4-triazol-1-yl 191-193.degree. 4.03 OCH.sub.3 OCH.sub.3 H  CH 1,2,4-triazol-1-yl 166-168.degree. 4.04 OCHF.sub.2 CH.sub.3 H  CH 1,2,4-triazol-1-yl 187-189.degree. 4.05 OCH.sub.3 CH.sub.2 OCH.sub.3 H  CH 1,2,4-triazol-1-yl 180-181.degree. 4.06 Cl   OCH.sub.3 H  CH 1,2,4-triazol-1-yl 157-159.degree. 4.07 OCH.sub.3 OCH.sub.3 H  N  1,2,4-triazol-1-yl 197-200.degree. (dec.) 4.08 N(CH.sub.3).sub.2 OCH.sub.3 H  N  1,2,4-triazol-1-yl 206-208.degree. 4.09 CH.sub.3 CH.sub.3 H  CH benztriazol-1-yl 204-205.degree. 4.10 OCH.sub.3 CH.sub.3 H  CH benztriazol-1-yl 165-167.degree. 4.11 OCH.sub.3 OCH.sub.3 H  CH benztriazol-1-yl 168-170.degree. 4.12 OCH.sub.3 CH.sub.2 OCH.sub.3 H  CH benztriazol-1-yl 132-134.degree. 4.13 OCHF.sub.2 CH.sub.3 H  CH benztriazol-1-yl 142-144.degree. 4.14 CH.sub.3 OCH.sub.3 H  CH 5(6)-nitro-benztriazol-1-yl 190-193.degree.* 4.15 OCH.sub.3 OCH.sub.3 H  CH 5(6)-nitro-benztriazol-1-yl 173-175.degree.* 4.16 CH.sub.3 OCH.sub.3 H  CH 5(6)-chlorobenztriazol-1-yl 156-168.degree.* 4.17 N(CH.sub.3).sub.2 OCH.sub.3 H  N  benztriazol-1-yl 222-224.degree. 4.18 CH.sub.3 CH.sub.3 H  CH 4aHcarbazol-1-yl 153-155.degree. 4.19 CH.sub.3 CH.sub.3 H  CH 2-methyl-benzimidazol-1-yl 207-212.degree. 4.20 CH.sub.3 CH.sub.3 H  CH 2,3-dimethylindol-1-yl 4.21 CH.sub.3 OCH.sub.3 H  N  2,3-dimethylindol-1-yl 4.22 OCHF.sub.2 CH.sub.3 H  CH 2,3-dimethylindol-1-yl 4.23 CH.sub.3 CH.sub.3 H  CH 2,4,5-tribromimidazol-1-yl 4.24 CH.sub.3 CH.sub.3 H  CH 2,4,5-tribromimidazol-1-yl 4.25 N(CH.sub.3).sub.2 OCH.sub.3 H  N  2,4,5-tribromimidazol-1-yl 4.26 CH.sub.3 OCH.sub.3 H  CH pyrazol-1-yl 4.27 OCHF.sub.2 CH.sub.3 H  CH pyrazol-1-yl 4.28 Cl   OCH.sub.3 H  N  pyrazol-1-yl 4.29 CH.sub.3 OCH.sub.3 CH.sub.3 CH 1,2,4-triazol-1-yl __________________________________________________________________________ *mixture of isomers N-2-chlorophenylsulfonyl-N'-(4-chlorophenylthiomethyl)-N'-(4,6-dimethylpyr imidin-2-yl)urea ##STR38##

7.5 g (0.027 mole) of 2-(4-chlorophenylthio)methylamino-4,6-dimethylpyrimidine are suspended in 50 ml of absolute acetonitrile and then 5.8 g (0.027 mole) of 2-chlorophenylisocyanate are added. The batch is stirred for 24 hours at room temperature, then the solvent is removed in a rotary evaporator and the residue is taken up in ethyl acetate. The solution is purified by chromatography through a column of silica gel eluted with ethyl acetate/cyclohexane. The title compound precipitates in crystalline form after removal of the solvent by evaporation. Yield: 6.0 g (45% of theory). Melting point: 132.degree.-135.degree. C. N-(2-difluoromethoxyphenylsulfonyl)-N'-(p-tolylulfonylmethyl)-N'-(4-difluo rom ethoxy-6-methylpyrimidin-2-yl)urea ##STR39##

5.5 g (0.016 mole) of 4-difluoromethoxy-6-methyl-2-p-tolylsulfonylmethylaminopyrimidine are suspended in 50 ml of absolute dioxan and then 4 g (0.016 mole) of 2-difluoromethoxyphenylisocyanate are stirred into the suspension. Stirring is continued for 3 hours at room temperature to give a clear solution, which is concentrated in a rotary evaporator. The residue crystallises spontaneously when stirred in ether. The crystals are filtered with suction and dried, affording 8 g (84% of theory) of crystalline title compound with a melting point of 159.degree.-164.degree. C. (dec.). N-(2-chlorophenylsulfonyl)-N'-(pyrrolidinothiocarbonylthiomethyl)-N'-(4,6- dimethylpyrimidin-2-yl)urea ##STR40##

5.5 g (0.019 mole) of 2-(pyrrolidinothiocarbonylthiomethyl)-4,6-dimethylpyrimidine are suspended in 30 ml of absolute acetonitrile and then 4.3 g (0.019 mole) of 2-chlorophenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 5 hours at room temperature to give first a clear solution from which the final product precipitates after a time. The reaction mixture is cooled and then filtered with suction, affording 6 g (63% of theory) of title compound which melts 131.degree.-133.degree. C. with decomposition. N-(2-chlorophenylsulfonyl)-N'-(1,2,4-triazol-1-ylmethyl)-N'-(4,6-dimethylp yrimidin-2-yl)urea ##STR41##

4 g (0.019 mole) of 2-(1,2,4-triazol-1-ylmethylamino)-4,6-dimethylpyrimidine are suspended in 100 ml of absolute acetonitrile and then 4.3 g (0.019 mole) of 2-chlorophenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 24 hours at room temperature and the resultant solution is finally concentrated in a rotary evaporator. Crystals of the title compound precipitate and are recrystallised from ethyl acetate, affording 5 g (62% of theory) of the above urea, which melts at 152.degree.-157.degree. C. N-(2-methoxycarbonylphenylsulfonyl)-N'-(benztriazol-1-methyl)-N'-(4,6-dime thylpyrimidin-2-yl)urea ##STR42##

6.5 g (0.026 mole) of 2-(benztriazol-1-ylmethylaminop)-4,6-dimethylpyrimidine are suspended in 70 ml of absolute dioxan and then 6.2 g (0.026 mole) of 2-methoxycarbonylphenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 24 hours at room temperature and the resultant solution is concentrated in a rotary evaporator. The residue is taken up in ethyl acetate and the solution is purified by chromatography through a column of silica gel eluted with ethyl acetate/cyclohexane. The solvent is evaporated off, affording 7.5 g (58% of theory) of crystalline title compound with a melting point of 178.degree.-180.degree. C. (dec.).

The following compounds are prepared by procedures analogous to those described in Examples 9-13: __________________________________________________________________________ ##STR43## No R.sup.1  R.sup.5 m R.sup.9       E  m.p.(.degree.C.) __________________________________________________________________________ 5.001 COOCH.sub.3 H       2 p-tolyl       CH 159-160.degree. 5.002 COOCH.sub.3 H       0 p-tolyl       CH 5.003 COOCH.sub.3 H       2 4-chlorophenyl CH 5.004 COOCH.sub.3 H       0 4-chlorophenyl CH 141-144.degree. 5.005 COOCH.sub.3 H       0 acetyl        CH 5.006 COOCH.sub.3 H       0 benzoyl       CH 5.007 COOCH.sub.3 H       2 CH.sub.3      CH 130-135.degree. (dec.) 5.008 COOCH.sub.3 H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.009 COOCH.sub.3 H       2 CH(CH.sub.3).sub.2 CH 5.010 COOCH.sub.3 H       2 benzyl        CH 5.011 COOCH.sub. 3 H       2 phenyl        CH 5.012 COOCH.sub.3 H       0 phenyl        CH 5.013 COOCH.sub.3 H       2 4-bromophenyl CH 5.014 COOCH.sub.3 H       0 4-bromophenyl CH 5.015 COOCH.sub.3 H       2 2-chlorophenyl CH 5.016 COOCH.sub.3 H       0 2-chlorophenyl CH 5.017 COOCH.sub.3 H       0 CH.sub.3      CH 5.018 COOCH.sub.3 H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.019 COOCH.sub.3 H       0 CH(CH.sub.3).sub.2 CH 5.020 COOCH.sub.3 H       0 benzyl        CH 5.021 COOCH.sub.3 H       2 .beta.-naphthyl CH 5.022 COOCH.sub.3 H       0 .beta.-naphthyl CH 178-183.degree. (dec.) 5.023 COOCH.sub.3 H       2 1,2,4-trichlorophenyl CH 5.024 COOCH.sub.3 H       0 1,2,4-trichlorophenyl CH 5.025 COOCH.sub.3 H       2 .alpha.-naphthyl CH 5.026 COOCH.sub.3 H       2 .alpha.-naphthyl CH 5.027 COOCH.sub.3 H       0 CH.sub.2 COOCH.sub.3 CH 5.028 COOCH.sub.3 H       2 4-fluorophenyl CH 5.029 COOCH.sub.3 H       0 4-fluorophenyl CH 5.030 COOCH.sub.3 H       0 4-nitrophenyl CH 5.031 COOCH.sub.3 H       0 4-nitrophenyl CH 5.032 COOCH.sub.3 H       2 2-nitrophenyl CH 5.033 COOCH.sub.3 H       0 2-nitrophenyl CH 5.034 COOCH.sub.3 H       2 2-trifluoromethyl CH 5.035 COOCH.sub.3 H       0 2-trifluoromethyl CH 5.036 COOCH.sub.3 H       2 4-methoxyphenyl CH 5.037 COOCH.sub.3 H       0 4-methoxyphenyl CH 5.038 COOCH.sub.3 H       2 2-methoxyphenyl CH 5.039 COOCH.sub.3 H       0 2-methoxyphenyl CH 5.040 COOCH.sub.3 H       2 2,4,6-trimethylphenyl CH 5.041 COOCH.sub.3 H       0 2,4,6-trimethylphenyl CH 5.042 COOCH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.043 COOCH.sub.3 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.044 COOCH.sub.3 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.045 COOCH.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.046 COOCH.sub.3 H       0 piperidinothiocarbonyl CH 5.047 COOCH.sub.3 H       0 anilidoacetyl CH 5.048 COOCH.sub.3 H       0 2,4-dichlorophenyl CH 5.049 COOCH.sub.3 H       2 2,4-dichlorophenyl CH 5.050 COOCH.sub.3 H       0 CH.sub.2 COOH CH 5.051 COOCH.sub.3 H       0 CH.sub.2 COOCH.sub.3 CH 154-156.degree. 5.052 COOCH.sub.3 H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 5.053 COOCH.sub.3 H       0 4-chlorophenyl N 5.054 COOCH.sub.3 H       0 p-tolyl       N 5.055 COOCH.sub.3 furyl-2- 0 2-hydroxycarbonylphenyl CH 5.056 COOCH.sub.3 furyl-2- 0 2-methoxycarbonylphenyl CH 5.057 COOCH.sub.3 furyl-2- 0 phenyl        CH 5.058 COOCH.sub.3 4-chlorophenyl 0 2-hydroxycarbonylphenyl CH 5.059 COOCH.sub.3 4-chlorophenyl 0 phenyl        CH 5.060 COOCH.sub.3 CH.sub.3 0 4-chlorophenyl CH 5.061 OCHF.sub. 2 H       2 p-tolyl       CH 152-157.degree. (dec.) 5.062 OCHF.sub.2 H       0 p-tolyl       CH 5.063 OCHF.sub.2 H       2 4-chlorophenyl CH 5.064 OCHF.sub.2 H       0 4-chlorophenyl CH 109-111.degree. 5.065 OCHF.sub.2 H       0 acetyl        CH 5.066 OCHF.sub.2 H       0 benzoyl       CH 155-158.degree.  dec. 5.067 OCHF.sub.2 H       2 CH.sub.3      CH 5.068 OCHF.sub.2 H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.069 OCHF.sub.2 H       2 CH(CH.sub.3).sub.2 CH 5.070 OCHF.sub.2 H       2 benzyl        CH 5.071 OCHF.sub.2 H       2 phenyl        CH 5.072 OCHF.sub.2 H       0 phenyl        CH 5.073 OCHF.sub.2 H       2 4-bromophenyl CH 5.074 OCHF.sub.2 H       0 4-bromophenyl CH 5.075 OCHF.sub.2 H       0 2-chlorophenyl CH 5.076 OCHF.sub.2 H       0 2-chlorophenyl CH 5.077 OCHF.sub.2 H       0 CH.sub.3      CH 5.078 OCHF.sub.2 H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.079 OCHF.sub.2 H       0 CH(CH.sub.3).sub.2 CH 5.080 OCHF.sub.2 H       0 benzyl        CH 5.081 OCHF.sub.2 H       2 .beta.-naphthyl CH 5.082 OCHF.sub.2 H       0 .beta.-naphthyl CH 162-164.degree. 5.083 OCHF.sub.2 H       2 1,2,4-trichlorophenyl CH 5.084 OCHF.sub.2 H       0 1,2,4-trichlorophenyl CH 5.085 OCHF.sub.2 H       2 .beta.-naphthyl CH 5.086 OCHF.sub.2 H       2 .beta.-naphthyl CH 5.087 OCHF.sub.2 H       0 CH.sub.2 COOCH.sub.3 CH 5.088 OCHF.sub.2 H       2 4-fluorophenyl CH 5.089 OCHF.sub.2 H       0 4-fluorophenyl CH 125-127.degree. 5.090 OCHF.sub.2 H       0 4-nitrophenyl CH 5.091 OCHF.sub.2 H       0 4-nitrophenyl CH 5.092 OCHF.sub.2 H       2 2-nitrophenyl CH 5.093 OCHF.sub.2 H       0 2-nitrophenyl CH 5.094 OCHF.sub.2 H       2 2-trifluoromethyl CH 5.095 OCHF.sub.2 H       0 2-trifluoromethyl CH 5.096 OCHF.sub.2 H       2 4-methoxyphenyl CH 5.097 OCHF.sub.2 H       0 4-methoxyphenyl CH 5.098 OCHF.sub.2 H       2 2-methoxyphenyl CH 5.099 OCHF.sub.2 H       0 2-methoxyphenyl CH 5.100 OCHF.sub.2 H       2 2,4,6-trimethylphenyl CH 5.101 OCHF.sub.2 H       0 2,4,6-trimethylphenyl CH 5.102 OCHF.sub.2 H       0 CSN(CH.sub.3).sub.2 CH 139-142.degree. dec. 5.103 OCHF.sub.2 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.104 OCHF.sub.2 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.105 OCHF.sub.2 H       0 pyrrolidinothiocarbonyl CH 136-139.degree. dec. 5.106 OCHF.sub.2 H       0 piperidinothiocarbonyl CH 5.107 OCHF.sub.2 H       0 Nphenylcarbamoylmethyl CH 110-112.degree. 5.108 OCHF.sub.2 H       0 2,4-dichlorophenyl CH 5.109 OCHF.sub.2 H       2 2,4-dichlorophenyl CH 5.110 OCHF.sub.2 H       0 CH.sub.2 COOH CH 5.111 OCHF.sub.2 H       0 CH.sub.2 COOCH.sub.3 CH 5.112 OCHF.sub.2 H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 5.113 OCHF.sub.2 H       0 4-chlorophenyl N 5.114 OCHF.sub.2 H       0 p-tolyl       N 5.115 OCHF.sub.2 Furyl-2- 0 2-hydroxycarbonylphenyl CH 5.116 OCHF.sub.2 Furyl-2- 0 2-methoxycarbonylphenyl CH 5.117 OCHF.sub.2 Furyl-2- 0 phenyl        CH 5.118 OCHF.sub.2 4-Chlorphenyl 0 2-hydroxycarbonylphenyl CH 5.119 OCHF.sub.2 4-Chlorphenyl 0 phenyl        CH 5.120 OCHF.sub.2 CH.sub.3 0 4-chlorophenyl CH 5.121 Cl       H       2 p-tolyl       CH 153-155.degree. 5.122 Cl       H       0 p-tolyl       CH  86-88 (dec.) 5.123 Cl       H       2 4-chlorophenyl CH 5.124 Cl       H       0 4-chlorophenyl CH 132-135.degree. dec. 5.125 Cl       H       0 acetyl        CH 5.126 Cl       H       0 benzoyl       CH 5.127 Cl       H       2 CH.sub.3      CH 5.128 Cl       H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.129 Cl       H       2 CH(CH.sub.3).sub.2 CH 5.130 Cl       H       2 benzyl        CH 146-147.degree. (dec.) 5.131 Cl       H       2 phenyl        CH 5.132 Cl       H       0 phenyl        CH 5.133 Cl       H       2 4-bromophenyl CH 150-153.degree. (dec.) 5.134 Cl       H       0 4-bromophenyl CH 5.135 Cl       H       2 2-chlorophenyl CH 5.136 Cl       H       0 2-chlorophenyl CH 5.137 Cl       H       0 CH.sub.3      CH 5.138 Cl       H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 5.139 Cl       H       0 CH(CH.sub.3).sub.2 CH 5.140 Cl       H       0 benzyl        CH 5.141 Cl       H       2 .beta.-naphthyl CH 5.142 Cl       H       0 .beta.-naphthyl CH 156-158.degree. 5.143 Cl       H       2 1,2,4-trichlorophenyl CH 5.144 Cl       H       0 1,2,4-trichlorophenyl CH 5.145 Cl       H       2 .alpha.-naphthyl CH 5.146 Cl       H       2 .alpha.-naphthyl CH 5.147 Cl       H       0 CH.sub.2 COOCH.sub.3 CH 5.148 Cl       H       2 4-fluorophenyl CH 5.149 Cl       H       0 4-fluorophenyl CH 5.150 Cl       H       0 4-nitrophenyl CH 5.151 Cl       H       0 4-nitrophenyl CH 5.152 Cl       H       2 2-nitrophenyl CH 5.153 Cl       H       0 2-nitrophenyl CH 5.154 Cl       H       2 2-trifluoromethyl CH 5.155 Cl       H       0 2-trifluoromethyl CH 5.156 Cl       H       2 4-methoxyphenyl CH 5.157 Cl       H       0 4-methoxyphenyl CH 5.158 Cl       H       2 2-methoxyphenyl CH 5.159 Cl       H       0 2-methoxyphenyl CH 5.160 Cl       H       2 2,4,6-trimethylphenyl CH 5.161 Cl       H       0 2,4,6-trimethylphenyl CH 5.162 Cl       H       0 CSN(CH.sub.3).sub.2 CH 5.163 Cl       H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.164 Cl       H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 5.165 Cl       H       0 pyrrolidinothiocarbonyl CH 131-133.degree. dec. 5.166 Cl       H       0 piperidinothiocarbonyl CH 5.167 Cl       H       0 Nphenylcarbamoylmethyl CH 110-112.degree. 5.168 Cl       H       0 2,4-dichlorophenyl CH 5.169 Cl       H       2 2,4-dichlorophenyl CH 5.170 Cl       H       0 CH.sub.2 COOH CH 123-125.degree. (dec.) 5.171 Cl       H       0 CH.sub.2 COOCH.sub.3 CH 5.172 Cl       H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 5.173 Cl       H       0 4-chlorophenyl N 5.174 Cl       H       0 p-tolyl       N 5.175 Cl       furyl-2- 0 2-hydroxycarbonylphenyl CH 5.176 Cl       furyl-2- 0 2-methoxycarbonylphenyl CH 5.177 Cl       furyl-2- 0 phenyl        CH 5.178 Cl       4-chlorophenyl 0 2-hydroxycarbonylphenyl CH 5.179 Cl       4-chlorophenyl 0 phenyl        CH 5.180 Cl       CH.sub.3 0 4-chlorophenyl CH 5.181 OCH.sub.3 H       0 phenyl        CH 5.182 OCH.sub.3 H       2 phenyl        CH 5.183 OCH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.184 OCH.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.185 OCH.sub.3 H       0 CH.sub.3      CH 5.186 OCH.sub.3 H       2 CH.sub.3      CH 5.187 NO.sub.2 H       0 phenyl        CH 5.188 NO.sub.2 H       2 phenyl        CH 5.189 NO.sub.2 H       0 CSN(CH.sub.3).sub.2 CH 5.190 NO.sub.2 H       0 pyrrolidinothiocarbonyl CH 5.191 NO.sub.2 H       0 CH.sub.3      CH 5.192 NO.sub.2 H       2 CH.sub.3      CH 5.193 CF.sub.3 H       0 phenyl        CH 5.194 CF.sub.3 H       2 phenyl        CH 5.195 CF.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.196 CF.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.197 CF.sub.3 H       0 CH.sub.3      CH 5.198 CF.sub.3 H       2 CH.sub.3      CH 5.199 OSO.sub.2 CH.sub.3 H       0 phenyl        CH 5.200 OSO.sub.2 CH.sub.3 H       2 phenyl        CH 5.201 OSO.sub.2 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.202 OSO.sub.2 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.203 OSO.sub.2 CH.sub.3 H       0 CH.sub.3      CH 5.204 OSO.sub.2 CH.sub.3 H       2 CH.sub.3      CH 5.205 OSO.sub.2 C.sub.3 H.sub.7 n H       2 phenyl        CH 5.206 OSO.sub.2 C.sub.3 H.sub.7 n H       2 phenyl        CH 5.207 OSO.sub.2 C.sub.3 H.sub.7 n H       0 CSN(CH.sub.3).sub.2 CH 5.208 OSO.sub.2 C.sub.3 H.sub.7 n H       0 pyrrolidinothiocarbonyl CH 5.209 OSO.sub.2 C.sub.3 H.sub.7 n H       2 CH.sub.3      CH 5.210 OSO.sub.2 C.sub.3 H.sub.7 n H       0 CH.sub.3      CH 5.211 SO.sub.2 N(CH.sub.3).sub.2 H       0 phenyl        CH 5.212 SO.sub.2 N(CH.sub.3).sub.2 H       2 phenyl        CH 5.213 SO.sub.2 N(CH.sub.3).sub.2 H       0 CSN(CH.sub.3).sub.2 CH 5.214 SO.sub.2 N(CH.sub.3).sub.2 H       0 pyrrolidinothiocarbonyl CH 5.215 SO.sub.2 N(CH.sub.3).sub.2 H       0 CH.sub.3      CH 5.216 SO.sub.2 N(CH.sub.3).sub.2 H       2 CH.sub.3      CH 5.217 CH.sub.3 H       0 phenyl        CH 5.218 CH.sub.3 H       2 phenyl        CH 5.219 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.220 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.221 CH.sub.3 H       0 CH.sub.3      CH 5.222 CH.sub.3 H       2 CH.sub.3      CH 5.223 SO.sub.2 CH.sub.3 H       0 phenyl        CH 5.224 SO.sub.2 CH.sub.3 H       2 phenyl        CH 5.225 SO.sub.2 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 5.226 SO.sub.2 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 5.227 SO.sub.2 CH.sub.3 H       0 CH.sub.3      CH 5.228 SO.sub.2 CH.sub.3 H       2 CH.sub.3      CH 5.229 CH.sub.3 H       2 p-tolyl       CH 148-150.degree. dec. 5.230 CH.sub.3 H       0 morpholinothiocarbonyl CH 145-146.degree. dec. 5.231 OCHF.sub.2 H       0 morpholinothiocarbonyl CH 132-134.degree. dec. 5.232 OCHF.sub.2 H       0 4-fluorophenyl CH 125-127.degree. 5.233 COOCH.sub.3 H       0 4-fluorophenyl CH 5.234 COOCH.sub.3 H       2 4-fluorophenyl CH 5.235 CH.sub.3 H       2 benzyl        CH 146-148.degree. dec. 5.236 CH.sub.3 H       2 4-bromophenyl CH 141-143.degree. dec. 5.237 Cl       CH.sub.3 2 p-tolyl       CH 126-129.degree. dec. 5.238 Cl       H       0 2-carboxyphenyl CH 134-138.degree. dec. 5.239 2,6-Cl.sub.2 H       2 benzyl        CH 147-151.degree. dec. 5.240 2,6-Cl.sub.2 H       0 .beta.-naphthyl CH 149-152.degree. 5.241 2,6-Cl.sub.2 H       2 p-tolyl       CH 163-166.degree. dec. 5.242 phenyl   H       2 CH.sub.3      CH 162-166.degree. dec. 5.243 phenyl   H       2 p-tolyl       CH 154-157.degree. dec. 5.244 phenyl   H       0 CSN(CH.sub.3).sub.2 CH 143-145.degree. dec. 5.245 phenyl   H       0 CH.sub.2COOCH.sub.3 CH 172-174.degree. dec. 5.246 phenyl   H       0 CH.sub.2CH.sub.2COOH CH 155-157.degree. dec. 5.247 phenyl   H       0 CH(CH.sub.3)COOH CH 150-152.degree.  dec. 5.248 Cl       H       2 phenyl        N 5.249 Cl       H       2 p-tolyl       N 5.250 COOCH.sub.3 H       2 CH.sub.3      N 5.251 OCHF.sub.2 H       2 p-tolyl       N 5.252 NO.sub.2 H       0 C.sub.2 H.sub.4 COOH CH 121-124.degree. 5.253 CF.sub.3 H       0 4-chlorophenyl CH 118-121.degree. __________________________________________________________________________ __________________________________________________________________________ ##STR44## __________________________________________________________________________ No R.sup.1 R.sup.5 m R.sup.9       E  m.p. (.degree.C.) __________________________________________________________________________ 6.001 COOCH.sub.3 H       2 p-tolyl       CH 148-150.degree. (dec.) 6.002 COOCH.sub.3 H       0 p-tolyl       CH 6.003 COOCH.sub.3 H       2 4-chlorophenyl CH 6.004 COOCH.sub.3 H       0 4-chlorophenyl CH 6.005 COOCH.sub.3 H       0 acetyl        CH 6.006 COOCH.sub.3 H       0 benzoyl       CH 6.007 COOCH.sub.3 H       2 CH.sub.3      CH 6.008 COOCH.sub.3 H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.009 COOCH.sub.3 H       2 CH(CH.sub.3).sub.2 CH 6.010 COOCH.sub.3 H       2 benzyl        CH 136-137.degree. (dec.) 6.011 COOCH.sub.3 H       2 phenyl        CH 141-142.degree. (dec.) 6.012 COOCH.sub.3 H       0 phenyl        CH 6.013 COOCH.sub.3 H       2 4-bromophenyl CH 134-135.degree. (dec.) 6.014 COOCH.sub.3 H       0 4-bromophenyl CH 6.015 COOCH.sub.3 H       2 2-chlorophenyl CH 6.016 COOCH.sub.3 H       0 2-chlorophenyl CH 6.017 COOCH.sub.3 H       0 CH.sub.3      CH 6.018 COOCH.sub.3 H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.019 COOCH.sub.3 H       0 CH(CH.sub.3).sub.2 CH 6.020 COOCH.sub.3 H       0 benzyl        CH 6.021 COOCH.sub.3 H       2 .beta.-naphthyl CH 140-141.degree. (dec.) 6.022 COOCH.sub.3 H       0 .beta.-naphthyl CH 6.023 COOCH.sub.3 H       2 1,2,4-trichlorophenyl CH 6.024 COOCH.sub.3 H       0 1,2,4-trichlorophenyl CH 6.025 COOCH.sub.3 H       2 .alpha.-naphthyl CH 6.026 COOCH.sub.3 H       2 .alpha.-naphthyl CH 6.027 COOCH.sub.3 H       0 CH.sub.2 COOCH.sub.3 CH 6.028 COOCH.sub.3 H       2 4-fluorophenyl CH 6.029 COOCH.sub.3 H       0 4-fluorophenyl CH 6.030 COOCH.sub.3 H       0 4-nitrophenyl CH 6.031 COOCH.sub.3 H       0 4-nitrophenyl CH 6.032 COOCH.sub.3 H       2 2-nitrophenyl CH 6.033 COOCH.sub.3 H       0 2-nitrophenyl CH 6.034 COOCH.sub.3 H       2 2-trifluoromethylphenyl CH 6.035 COOCH.sub.3 H       0 2-trifluoromethylphenyl CH 6.036 COOCH.sub.3 H       2 4-methoxyphenyl CH 6.037 COOCH.sub.3 H       0 4-methoxyphenyl CH 6.038 COOCH.sub.3 H       2 2-methoxyphenyl CH 6.039 COOCH.sub.3 H       0 2-methoxyphenyl CH 6.040 COOCH.sub.3 H       2 2,4,6-trimethylphenyl CH 133-134.degree. (dec.) 6.041 COOCH.sub.3 H       0 2,4,6-trimethylphenyl CH 6.042 COOCH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.043 COOCH.sub.3 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 139-140.degree. (dec.) 6.044 COOCH.sub.3 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 N 6.045 COOCH.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.046 COOCH.sub.3 H       0 piperidinothiocarbonyl CH 6.047 COOCH.sub.3 H       0 Nphenylcarbamoylmethyl CH 6.048 COOCH.sub.3 H       0 2,4-dichlorophenyl CH 6.049 COOCH.sub.3 H       2 2,4-dichlorophenyl CH 6.050 COOCH.sub.3 H       0 CH.sub.2 COOH CH 6.051 COOCH.sub.3 H       0 CH.sub.2 COOCH.sub.3 CH 6.052 COOCH.sub.3 H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 6.053 COOCH.sub.3 H       0 4-Chlorophenyl N 6.054 COOCH.sub.3 H       0 p-tolyl       N 6.055 COOCH.sub.3 furyl-2- 0 2-hydroxycarbonylphenyl CH 6.056 COOCH.sub.3 furyl-2- 0 2-methoxycarbonylphenyl CH 6.057 COOCH.sub.3 furyl-2- 0 phenyl        CH 6.058 COOCH.sub.3 4-chlorophenyl 0 2-hydroxycarbonylphenyl CH 6.059 COOCH.sub.3 4-chlorophenyl 0 phenyl        CH 6.060 COOCH.sub.3 CH.sub.3 0 4-chlorophenyl CH 6.061 OCHF.sub.2 H       2 p-tolyl       CH 142-143.degree. 6.062 OCHF.sub.2 H       0 p-tolyl       CH 6.063 OCHF.sub.2 H       2 4-chlorophenyl CH 6.064 OCHF.sub.2 H       0 4-chlorophenyl CH 6.065 OCHF.sub.2 H       0 acetyl        CH 6.066 OCHF.sub.2 H       0 benzoyl       CH 6.067 OCHF.sub.2 H       2 CH.sub.3 CH 6.068 OCHF.sub.2 H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.069 OCHF.sub.2 H       2 CH(CH.sub.3).sub.2 CH 6.070 OCHF.sub.2 H       2 benzyl        CH 6.071 OCHF.sub.2 H       2 phenyl        CH 6.072 OCHF.sub.2 H       0 phenyl        CH 6.073 OCHF.sub.2 H       2 4-bromophenyl CH 6.074 OCHF.sub.2 H       0 4-bromophenyl CH 6.075 OCHF.sub.2 H       2 2-chlorophenyl CH 6.076 OCHF.sub.2 H       0 2-chlorophenyl CH 6.077 OCHF.sub.2 H       0 CH.sub.3 CH 6.078 OCHF.sub.2 H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.079 OCHF.sub.2 H       0 CH(CH.sub.3).sub.2 CH 6.080 OCHF.sub.2 H       0 benzyl        CH 6.081 OCHF.sub.2 H       2 .beta.-naphthyl CH 6.082 OCHF.sub.2 H       0 .beta.-naphthyl CH 6.083 OCHF.sub.2 H       2 1,2,4-trichlorophenyl CH 6.084 OCHF.sub. 2 H       0 1,2,4-trichlorophenyl CH 6.085 OCHF.sub.2 H       2 .alpha.-naphthyl CH 6.086 OCHF.sub.2 H       2 .alpha.-naphthyl CH 6.087 OCHF.sub.2 H       0 CH.sub.2 COOCH.sub.3 CH 6.088 OCHF.sub.2 H       2 4-fluorophenyl CH 6.089 OCHF.sub.2 H       0 4-fluorophenyl CH 6.090 OCHF.sub.2 H       0 4-nitrophenyl CH 6.091 OCHF.sub.2 H       0 4-nitrophenyl CH 6.092 OCHF.sub.2 H       2 2-nitrophenyl CH 6.093 OCHF.sub.2 H       0 2-nitrophenyl CH 6.094 OCHF.sub.2 H       2 2-trifluoromethyl CH 6.095 OCHF.sub.2 H       0 2-trifluoromethyl CH 6.096 OCHF.sub.2 H       2 4-methoxyphenyl CH 6.097 OCHF.sub.2 H       0 4-methoxyphenyl CH 6.098 OCHF.sub.2 H       2 2-methoxyphenyl CH 6.099 OCHF.sub.2 H       0 2-methoxyphenyl CH 6.100 OCHF.sub.2 H       2 2,4,6-trimethylphenyl CH 6.101 OCHF.sub.2 H       0 2,4,6-trimethylphenyl CH 6.102 OCHF.sub.2 H       0 CSN(CH.sub.3).sub.2 CH 6.103 OCHF.sub.2 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 6.104 OCHF.sub.2 H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 6.105 OCHF.sub.2 H       0 pyrrolidinothiocarbonyl CH 6.106 OCHF.sub.2 H       0 piperidinothiocarbonyl CH 6.107 OCHF.sub.2 H       0 Nphenylcarbamoylmethyl CH 6.108 OCHF.sub.2 H       0 2,4-dichlorophenyl CH 6.109 OCHF.sub.2 H       2 2,4-dichlorophenyl CH 6.110 OCHF.sub.2 H       0 CH.sub.2 COOH CH 6.111 OCHF.sub.2 H       0 CH.sub.2 COOCH.sub.3 CH 6.112 OCHF.sub.2 H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 6.113 OCHF.sub.2 H       0 4-chlorophenyl N 6.114 OCHF.sub.2 H       0 p-tolyl       N 6.115 OCHF.sub.2 furyl-2- 0 2-hydroxycarbonylphenyl CH 6.116 OCHF.sub.2 furyl-2- 0 2-methoxycarbonylphenyl CH 6.117 OCHF.sub.2 furyl-2- 0 phenyl        CH 6.118 OCHF.sub.2 4-chlorophenyl 0 2-hydroxycarbonylphenyl CH 6.119 OCHF.sub.2 4-chlorophenyl 0 phenyl        CH 6.120 OCHF.sub.2 CH.sub.3 0 4-chlorophenyl CH 6.121 Cl      H       2 p-tolyl       CH 6.122 Cl      H       0 p-tolyl       CH 6.123 Cl      H       2 4-chlorophenyl CH 6.124 Cl      H       0 4-chlorophenyl CH 6.125 Cl      H       0 acetyl        CH 6.126 Cl      H       0 benzoyl       CH 6.127 Cl      H       2 CH.sub.3      CH 6.128 Cl      H       2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.129 Cl      H       2 CH(CH.sub.3).sub.2 CH 6.130 Cl      H       2 benzyl        CH 6.131 Cl      H       2 phenyl        CH 6.132 Cl      H       0 phenyl        CH 6.133 Cl      H       2 4-bromophenyl CH 6.134 Cl      H       0 4-bromophenyl CH 6.135 Cl      H       2 2-chlorophenyl CH 6.136 Cl      H       0 2-chlorophenyl CH 6.137 Cl      H       0 CH.sub.3 CH 6.138 Cl      H       0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 6.139 Cl      H       0 CH(CH.sub.3).sub.2 CH 6.140 Cl      H       0 benzyl        CH 6.141 Cl      H       2 .beta.-naphthyl CH 6.142 Cl      H       0 .beta.-naphthyl CH 6.143 Cl      H       2 1,2,4-trichlorophenyl CH 6.144 Cl      H       0 1,2,4-trichlorophenyl CH 6.145 Cl      H       2 .alpha.-naphthyl CH 6.146 Cl      H       2 .alpha.-naphthyl CH 6.147 Cl      H       0 CH.sub.2 COOCH.sub.3 CH 6.148 Cl      H       2 4-fluorophenyl CH 6.149 Cl      H       0 4-fluorophenyl CH 6.150 Cl      H       0 4-nitrophenyl CH 6.151 Cl      H       0 4-nitrophenyl CH 6.152 Cl      H       2 2-nitrophenyl CH 6.153 Cl      H       0 2-nitrophenyl CH 6.154 Cl      H       2 2-trifluoromethyl CH 6.155 Cl      H       0 2-trifluoromethyl CH 6.156 Cl      H       2 4-methoxyphenyl CH 6.157 Cl      H       0 4-methoxyphenyl CH 6.158 Cl      H       2 2-methoxyphenyl CH 6.159 Cl      H       0 2-methoxyphenyl CH 6.160 Cl      H       2 2,4,6-trimethylphenyl CH 6.161 Cl      H       0 2,4,6-trimethylphenyl CH 6.162 Cl      H       0 CSN(CH.sub.3).sub.2 CH 6.163 Cl      H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 6.164 Cl      H       0 CSN(CH.sub.2 CH.sub.3).sub.2 CH 6.165 Cl      H       0 pyrrolidinothiocarbonyl CH 6.166 Cl      H       0 piperidinothiocarbonyl CH 6.167 Cl      H       0 Nphenylcarbamoylmethyl CH 6.168 Cl      H       0 2,4-dichlorophenyl CH 6.169 Cl      H       2 2,4-dichlorophenyl CH 6.170 Cl      H       0 CH.sub.2 COOH CH 6.171 Cl      H       0 CH.sub.2 COOCH.sub.3 CH 6.172 Cl      H       0 CH.sub.2 CON(CH.sub.3).sub.2 CH 6.173 Cl      H       0 4-chlorophenyl N 6.174 Cl      H       0 p-tolyl       N 6.175 Cl      furyl-2- 0 2-hydroxycarbonylphenyl CH 6.176 Cl      furyl-2- 0 2-methoxycarbonylphenyl CH 6.177 Cl      furyl-2- 0 phenyl        CH 6.178 Cl      4-chlorophenyl 0 2-hydroxycarbonylphenyl CH 6.179 Cl      4-chlorophenyl 0 phenyl        CH 6.180 Cl      CH.sub.3 0 4-chlorophenyl CH 6.181 OCH.sub.3 H       0 phenyl        CH 6.182 OCH.sub.3 H       2 phenyl        CH 6.183 OCH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.184 OCH.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.185 OCH.sub.3 H       0 CH.sub.3      CH 6.186 OCH.sub.3 H       2 CH.sub.3      CH 6.187 NO.sub.2 H       0 phenyl        CH 6.188 NO.sub.2 H       2 phenyl        CH 6.189 NO.sub.2 H       0 CSN(CH.sub.3).sub.2 CH 6.190 NO.sub.2 H       0 pyrrolidinothiocarbonyl CH 6.191 NO.sub.2 H       0 CH.sub.3      CH 6.192 NO.sub.2 H       2 CH.sub.3      CH 6.193 CF.sub.3 H       0 phenyl        CH 6.194 CF.sub.3 H       2 phenyl        CH 6.195 CF.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.196 CF.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.197 CF.sub.3 H       0 CH.sub.3      CH 6.198 CF.sub.3 H       2 CH.sub.3      CH 6.199 OSO.sub.2 CH.sub.3 H       0 phenyl        CH 6.200 OSO.sub.2 CH.sub.3 H       2 phenyl        CH 6.201 OSO.sub.2 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.202 OSO.sub.2 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.203 OSO.sub.2 CH.sub.3 H       0 CH.sub.3      CH 6.204 OSO.sub.2 CH.sub.3 H       2 CH.sub.3      CH 6.205 OSO.sub.2 C.sub.3 H.sub.7 n H       2 phenyl        CH 6.206 OSO.sub.2 C.sub.3 H.sub.7 n H       2 phenyl        CH 6.207 OSO.sub.2 C.sub.3 H.sub.7 n H       0 CSN(CH.sub.3).sub.2 CH 6.208 OSO.sub.2 C.sub.3 H.sub.7 n H       0 pyrrolidinothiocarbonyl CH 6.209 OSO.sub.2 C.sub.3 H.sub.7 n H       2 CH.sub.3      CH 6.210 OSO.sub.2 C.sub.3 H.sub.7 n H       0 CH.sub.3      CH 6.211 SO.sub.2 N(CH.sub.3).sub.2 H       0 phenyl        CH 6.212 SO.sub.2 N(CH.sub.3).sub.2 H       2 phenyl        CH 6.213 SO.sub.2 N(CH.sub.3).sub.2 H       0 CSN(CH.sub.3).sub.2 CH 6.214 SO.sub.2 N(CH.sub.3).sub.2 H       0 pyrrolidinothiocarbonyl CH 6.215 SO.sub.2 N(CH.sub.3).sub.2 H       0 CH.sub.3      CH 6.216 SO.sub.2 N(CH.sub.3).sub.2 H       2 CH.sub.3      CH 6.217 CH.sub.3 H       0 phenyl        CH 6.218 CH.sub.3 H       2 phenyl        CH 6.219 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.220 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.221 CH.sub.3 H       0 CH.sub.3      CH 6.222 CH.sub.3 H       2 CH.sub.3      CH 6.223 SO.sub.2 CH.sub.3 H       0 phenyl        CH 6.224 SO.sub.2 CH.sub.3 H       2 phenyl        CH 6.225 SO.sub.2 CH.sub.3 H       0 CSN(CH.sub.3).sub.2 CH 6.226 SO.sub.2 CH.sub.3 H       0 pyrrolidinothiocarbonyl CH 6.227 SO.sub.2 CH.sub.3 H       0 CH.sub.3      CH 6.228 SO.sub.2 CH.sub.3 H       2 CH.sub.3      CH 6.229 phenyl  H       0 p-tolyl       CH 144-147.degree. 6.230 phenyl  H       2 p-tolyl       CH 141-144.degree. dec. 6.231 COOCH.sub.3 H       2 benzyl        N 6.232 COOCH.sub.3 H       2 phenyl        N 6.233 OCF.sub.2 CHF.sub.2 H       2 p-tolyl       CH 133-134.degree. 6.234 OCF.sub.2 CHF.sub.2 H       2 p-tolyl       CH 6.235 OCF.sub.2 CHF.sub.2 H       2 CH.sub.3      CH 6.236 OCF.sub.2 CHF.sub.2 H       2 phenyl        CH 6.237 OCF.sub.2 CHF.sub.2 H       2 4-chlorophenyl CH 6.238 OCF.sub.2 CHF.sub.2 H       2 .beta.-naphthyl CH 6.239 F       H       0 4-chlorophenyl CH 6.240 F       H       0 .beta.-naphthyl CH 158-154.degree. 6.241 F       H       2 .beta.-naphthyl CH 6.242 COOCH.sub.3 H       2 2-methoxycarbonylbenzyl CH  66-67.degree. 6.243 COOCH.sub.3 H       2 C.sub.3 H.sub.7 n CH 6.244 COOCH.sub.3 H       2 C.sub.2 H.sub.5 CH 6.245 COOCH.sub.3 H       2 2-difluoromethoxyphenyl CH 145-147.degree. 6.246 COOCH.sub.3 H       2 3,4-dichlorophenyl CH 6.247 COOCH.sub.3 H       2 3,5-dichlorophenyl CH 6.248 COOCH.sub.3 H       2 3-chlorophenyl CH 6.249 COOCH.sub.3 H       2 2-difluoromethylthiophenyl CH 6.250 COOCH.sub.3 H       2 3-trifluoromethylphenyl CH 6.251 COOCH.sub.3 H       2 2,5-dimethylphenyl CH 6.252 COOC.sub.2 H.sub.5 H       2 CH.sub.3      CH 6.253 COOC.sub.2 H.sub.5 H       2 C.sub.3 H.sub.7 n CH 6.254 COOC.sub.2 H.sub.5 H       2 phenyl        CH 149.degree. 6.255 COOC.sub.2 H.sub.5 H       2 p-tolyl       CH 147.degree. 6.256 COOC.sub.2 H.sub.5 H       0 CSN(CH.sub.3).sub.2 CH 6.257 NO.sub.2 H       2 p-tolyl       CH 149-151.degree. (dec.) 6.258 NO.sub.2 H       2 4-chlorophenyl CH 164.degree. (dec.) __________________________________________________________________________ No. R.sup.1 (R.sup.2) R.sup.5 m R.sup.9       E  m.p. (.degree.C.) __________________________________________________________________________ 6.259 NO.sub.2 H       2 4-bromophenyl CH 6.260 NO.sub.2 H       2 .beta.-naphthyl CH 6.261 NO.sub.2 H       2 C.sub.2 H.sub.5 CH 6.262 NO.sub.2 H       2 C.sub.3 H.sub.7 n CH 6.263 NO.sub.2 H       2 benzyl        CH 6.264 NO.sub.2 H       2 2-methoxycarbonylbenzyl CH 6.265 NO.sub.2 H       2 4-methoxyphenyl CH 6.266 NO.sub.2 H       2 2-difluoromethoxyphenyl CH 6.267 NO.sub.2 H       2 mesityl       CH 6.268 OCF.sub.3 H       2 p-tolyl       CH 138-139.degree. (dec.) 6.269 OC.sub.2 H.sub.4 OCH.sub.3 H       2 p-tolyl       CH 135-137.degree. (dec.) 6.270 OC.sub.2 H.sub.4 Cl H       2 p-tolyl       CH 133-135.degree. (dec.) 6.271 OCClCHCl        2 p-tolyl       CH 143-144.degree. (dec.) 6.272 CF.sub.3        2 p-tolyl       CH 156-158.degree. (dec.) 6.273 OSO.sub.2 CH.sub.3 2 p-tolyl       CH 6.274 OSO.sub.2 N(CH.sub. 3).sub.2 2 p-tolyl       CH 6.275 OCH.sub.3       2 p-tolyl       CH 164.degree. (dec.) 6.276 OCH.sub.3       2 4-bromophenyl CH 165.degree. (dec.) 6.277 OCH.sub.3       2 .beta.-naphthyl CH 148-150.degree. (dec.) 6.278 OCH.sub.3       2 benzyl        CH 126-128.degree. (dec.) 6.279 CF.sub.3        2 p-tolyl       CH 156-158.degree. (dec.) 6.280 CF.sub.3        2 4-chlorophenyl CH 147-154.degree. (dec.) 6.281 CF.sub.3        2 .beta.-naphthyl CH 152-154.degree. (dec.) __________________________________________________________________________ ______________________________________ ##STR45## m.p. No   R.sup.1    R.sup.5  m   R.sup.9    E(.degree.C.) ______________________________________ 7.001 COOCH.sub.3 H        2   p-tolyl    CH153- 158.degree. dec. 7.002 COOCH.sub.3 H        0   p-tolyl    CH 7.003 COOCH.sub.3 H        2   4-chlorophenyl CH 7.004 COOCH.sub.3 H        0   4-chlorophenyl CH 7.005 COOCH.sub.3 H        0   acetyl     CH 7.006 COOCH.sub.3 H        0   benzoyl    CH 7.007 COOCH.sub.3 H        2   CH.sub.3   CH 7.008 COOCH.sub.3 H        2   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.009 COOCH.sub.3 H        2   CH(CH.sub.3).sub.2 CH 7.010 COOCH.sub.3 H        2   benzyl     CH 7.011 COOCH.sub.3 H        2   phenyl     CH 7.012 COOCH.sub.3 H        0   phenyl     CH 7.013 COOCH.sub.3 H        2   4-bromophenyl CH 7.014 COOCH.sub.3 H        0   4-bromophenyl CH 7.015 COOCH.sub.3 H        2   2-chlorophenyl CH 7.016 COOCH.sub.3 H        0   2-chlorophenyl CH 7.017 COOCH.sub.3 H        0   CH.sub.3   CH 7.018 COOCH.sub.3 H        0   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.019 COOCH.sub.3 H        0   CH(CH.sub.3).sub.2 CH 7.020 COOCH.sub.3 H        0   benzyl     CH 7.021 COOCH.sub.3 H        2   .beta.-naphthyl CH 7.022 COOCH.sub.3 H        0   .beta.-naphthyl CH 7.023 COOCH.sub.3 H        2   1,2,4-trichloro- CH phenyl 7.024 COOCH.sub.3 H        0   1,2,4-trichloro- CH phenyl 7.025 COOCH.sub.3 H        2   .alpha.-naphthyl CH 7.026 COOCH.sub.3 H        2   .alpha.-naphthyl CH 7.027 COOCH.sub.3 H        0   CH.sub.2 COOCH.sub.3 CH 7.028 COOCH.sub.3 H        2   4-fluorophenyl CH 7.029 COOCH.sub.3 H        0   4-fluorophenyl CH 7.030 COOCH.sub.3 H        0   4-nitrophenyl CH 7.031 COOCH.sub.3 H        0   4-nitrophenyl CH 7.032 COOCH.sub.3 H        2   2-nitrophenyl CH 7.033 COOCH.sub.3 H        0   2-nitrophenyl CH 7.034 COOCH.sub.3 H        2   2-trifluoromethyl CH 7.035 COOCH.sub.3 H        0   2-trifluoromethyl CH 7.036 COOCH.sub.3 H        2   4-methoxyphenyl CH 7.037 COOCH.sub.3 H        0   4-methoxyphenyl CH 7.038 COOCH.sub.3 H        2   2-methoxyphenyl CH 7.039 COOCH.sub.3 H        0   2-methoxyphenyl CH 7.040 COOCH.sub.3 H        2   2,4,6-trimethyl- CH phenyl 7.041 COOCH.sub.3 H        0   2,4,6-trimethyl- CH phenyl 7.042 COOCH.sub.3 H        0   CSN(CH.sub.3).sub.2 CH 7.043 COOCH.sub.3 H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.044 COOCH.sub.3 H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.045 COOCH.sub.3 H        0   pyrrolidinothio- CH carbonyl 7.046 COOCH.sub.3 H        0   piperidinothio- CH carbonyl 7.047 COOCH.sub.3 H        0   Nphenylcarba- CH moylmethyl 7.048 COOCH.sub.3 H        0   2,4-dichloro- CH phenyl 7.049 COOCH.sub.3 H        2   2,4-dichloro- CH phenyl 7.050 COOCH.sub.3 H        0   CH.sub.2 COOH CH 7.051 COOCH.sub.3 H        0   CH.sub.2 COO CH.sub.3 CH 7.052 COOCH.sub.3 H        0   CH.sub.2 CON(CH.sub.3).sub.2 CH 7.053 COOCH.sub. 3 H        0   4-chlorophenyl N 7.054 COOCH.sub.3 H        0   p-tolyl    N 7.055 COOCH.sub.3 furyl-2- 0   2-hydroxy- CH carbonylphenyl 7.056 COOCH.sub.3 furyl-2- 0   2-methoxy- CH carbonylphenyl 7.057 COOCH.sub.3 furyl-2- 0   phenyl     CH 7.058 COOCH.sub.3 4-chloro- 0   2-hydroxy- CH phenyl       carbonylphenyl 7.059 COOCH.sub.3 4-chloro- 0   phenyl     CH phenyl 7.060 COOCH.sub.3 CH.sub.3 0   4-chlorophenyl CH 7.061 OCHF.sub.2 H        2   p-tolyl    CH146- 150.degree. 7.062 OCHF.sub.2 H        0   p-tolyl    CH 7.063 OCHF.sub.2 H        2   4-chlorophenyl CH 7.064 OCHF.sub.2 H        0   4-chlorophenyl CH 7.065 OCHF.sub.2 H        0   acetyl     CH 7.066 OCHF.sub.2 H        0   benzoyl    CH 7.067 OCHF.sub.2 H        2   CH.sub.3   N 7.068 OCHF.sub.2 H        2   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.069 OCHF.sub.2 H        2   CH(CH.sub.3).sub.2 CH 7.070 OCHF.sub.2 H        2   benzyl     CH 7.071 OCHF.sub.2 H        2   phenyl     CH 7.072 OCHF.sub.2 H        0   phenyl     CH 7.073 OCHF.sub.2 H        2   4-bromophenyl CH 7.074 OCHF.sub.2 H        0   4-bromophenyl CH 7.075 OCHF.sub.2 H        2   2-chlorophenyl CH 7.076 OCHF.sub. 2 H        0   2-chlorophenyl CH 7.077 OCHF.sub.2 H        0   CH.sub.3   N 7.078 OCHF.sub.2 H        0   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.079 OCHF.sub.2 H        0   CH(CH.sub.3).sub.2 CH 7.080 OCHF.sub.2 H        0   benzyl     CH 7.081 OCHF.sub.2 H        2   .beta.-naphthyl CH 7.082 OCHF.sub.2 H        0   .beta.-naphthyl CH162- 164.degree. 7.083 OCHF.sub.2 H        2   1,2,4-trichloro- CH phenyl 7.084 OCHF.sub.2 H        0   2,4,5-trichloro- CH104- phenyl     107.degree. 7.085 OCHF.sub.2 H        2   .alpha.-naphthyl CH 7.086 OCHF.sub.2 H        2   .alpha.-naphthyl CH 7.087 OCHF.sub.2 H        0   CH.sub.2 COOCH.sub.3 CH 7.088 OCHF.sub.2 H        2   4-fluorophenyl CH 7.089 OCHF.sub.2 H        0   4-fluorophenyl CH 7.090 OCHF.sub.2 H        0   4-nitrophenyl CH 7.091 OCHF.sub.2 H        0   4-nitrophenyl CH 7.092 OCHF.sub.2 H        2   2-nitrophenyl CH 7.093 OCHF.sub.2 H        0   2-nitrophenyl CH 7.094 OCHF.sub.2 H        2   2-trifluoromethyl CH 7.095 OCHF.sub.2 H        0   2-trifluoromethyl CH 7.096 OCHF.sub.2 H        2   4-methoxyphenyl CH 7.097 OCHF.sub.2 H        0   4-methoxyphenyl CH 7.098 OCHF.sub.2 H        2   2-methoxyphenyl CH 7.099 OCHF.sub.2 H        0   2-methoxyphenyl CH 7.100 OCHF.sub.2 H        2   2,4,6-trimethyl- CH phenyl 7.101 OCHF.sub.2 H        0   2,4,6-trimethyl- CH phenyl 7.102 OCHF.sub.2 H        0   CSN(CH.sub.3).sub.2 CH 7.103 OCHF.sub.2 H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.104 OCHF.sub.2 H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.105 OCHF.sub.2 H        0   pyrrolidinothio- CH carbonyl 7.106 OCHF.sub.2 H        0   piperidinothio- CH carbonyl 7.107 OCHF.sub.2 H        0   Nphenylcarba- CH moylmethyl 7.108 OCHF.sub.2 H        0   2,4-dichlorophenyl CH 7.109 OCHF.sub.2 H        2   2,4-dichlorophenyl CH 7.110 OCHF.sub.2 H        0   CH.sub.2 COOH CH 7.111 OCHF.sub.2 H        0   CH.sub.2 COOCH.sub.3 CH 7.112 OCHF.sub.2 H        0   CH.sub.2 CON(CH.sub.3).sub.2 CH 7.113 OCHF.sub.2 H        0   4-Chlorophenyl N 7.114 OCHF.sub.2 H        0   p-tolyl    N 7.115 OCHF.sub.2 furyl-2- 0   2-hydroxy- CH carbonylphenyl 7.116 OCHF.sub.2 furyl-2- 0   2-methoxy- CH carbonylphenyl 7.117 OCHF.sub.2 furyl-2- 0   phenyl     CH 7.118 OCHF.sub.2 4-chloro- 0   2-hydroxy- CH phenyl       carbonylphenyl 7.119 OCHF.sub.2 4-chloro- 0   phenyl     CH phenyl 7.120 OCHF.sub.2 CH.sub.3 0   4-chlorophenyl CH 7.121 Cl         H        2   p-tolyl    CH 7.122 Cl         H        0   p-tolyl    CH 7.123 Cl         H        2   4-chlorophenyl CH 7.124 Cl         H        0   4-chlorophenyl CH 7.125 Cl         H        0   acetyl     CH 7.126 Cl         H        0   benzoyl    CH 7.127 Cl         H        2   CH.sub.3   CH 7.128 Cl         H        2   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.129 Cl         H        2   CH(CH.sub.3).sub.2 CH 7.130 Cl         H        2   benzyl     CH 7.131 Cl         H        2   phenyl     CH 7.132 Cl         H        0   phenyl     CH 7.133 Cl         H        2   4-bromophenyl CH 7.134 Cl         H        0   4-bromophenyl CH 7.135 Cl         H        2   2-chlorophenyl CH 7.136 Cl         H        0   2-chlorophenyl CH 7.137 Cl         H        0   CH.sub.3   CH 7.138 Cl         H        0   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH 7.139 Cl         H        0   CH(CH.sub.3).sub.2 CH 7.140 Cl         H        0   benzyl     CH 7.141 Cl         H        2   .beta.-naphthyl CH 7.142 Cl         H        0   .beta.-naphthyl CH156- 158.degree. dec. 7.143 Cl         H        2   1,2,4-trichloro- CH phenyl 7.144 Cl         H        0   1,2,4-trichloro- CH phenyl 7.145 Cl         H        2   .alpha.-naphthyl CH 7.146 Cl         H        2   .alpha.-naphthyl CH 7.147 Cl         H        0   CH.sub.2 COOCH.sub.3 CH 7.148 Cl         H        2   4-fluorophenyl CH 7.149 Cl         H        0   4-fluorophenyl CH 7.150 Cl         H        0   4-nitrophenyl CH 7.151 Cl         H        0   4-nitrophenyl CH 7.152 Cl         H        2   2-nitrophenyl CH 7.153 Cl         H        0   2-nitrophenyl CH 7.154 Cl         H        2   2-trifluoromethyl CH 7.155 Cl         H        0   2-trifluoromethyl CH 7.156 Cl         H        2   4-methoxyphenyl CH 7.157 Cl         H        0   4-methoxyphenyl CH 7.158 Cl         H        2   2-methoxyphenyl CH 7.159 Cl         H        0   2-methoxyphenyl CH 7.160 Cl         H        2   2,4,6-trimethyl- CH phenyl 7.161 Cl         H        0   2,4,6-trimethyl- CH phenyl 7.162 Cl         H        0   CSN(CH.sub.3).sub.2 CH 7.163 Cl         H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.164 Cl         H        0   CSN(CH.sub.2 CH.sub.3).sub.2 CH 7.165 Cl         H        0   pyrrolidinothio- CH carbonyl 7.166 Cl         H        0   piperidinothio- CH carbonyl 7.167 Cl         H        0   Nphenylcarba- CH moylmethyl 7.168 Cl         H        0   2,4-dichlorophenyl CH 7.169 Cl         H        2   2,4-dichlorophenyl CH 7.170 Cl         H        0   CH.sub.2 COOH CH 7.171 Cl         H        0   CH.sub.2 COO CH.sub.3 CH 7.172 Cl         H        0   CH.sub.2 CON(CH.sub.3).sub.2 CH 7.173 Cl         H        0   4-chlorophenyl N 7.174 Cl         H        0   p-tolyl    N 7.175 Cl         furyl-2- 0   2-hydroxy- CH carbonylphenyl 7.176 Cl         furyl-2- 0   2-methoxy- CH carbonylphenyl 7.177 Cl         furyl-2- 0   phenyl     CH 7.178 Cl         4-chloro- 0   2-hydroxy- CH phenyl       carbonylphenyl 7.179 Cl         4-chloro- 0   phenyl     CH phenyl 7.180 Cl         CH.sub.3 0   4-chlorophenyl CH 7.181 OCH.sub.3  H        0   phenyl     CH 7.182 OCH.sub.3  H        2   phenyl     CH 7.183 OCH.sub.3  H        0   CSN(CH.sub.3).sub.2 CH 7.184 OCH.sub.3  H        0   pyrrolidinothio- CH carbonyl 7.185 OCH.sub.3  H        0   CH.sub.3   CH 7.186 OCH.sub.3  H        2   CH.sub.3   CH 7.187 NO.sub.2   H        0   phenyl     CH 7.188 NO.sub.2   H        2   phenyl     CH 7.189 NO.sub.2   H        0   CSN(CH.sub.3).sub.2 CH 7.190 NO.sub.2   H        0   pyrrolidinothio- CH carbonyl 7.191 NO.sub.2   H        0   CH.sub.3   CH 7.192 NO.sub.2   H        2   CH.sub.3   CH 7.193 CF.sub.3   H        0   phenyl     CH 7.194 CF.sub.3   H        2   phenyl     CH 7.195 CF.sub.3   H        0   CSN(CH.sub.3).sub.2 CH 7.196 CF.sub.3   H        0   pyrrolidino- CH thiocarbonyl 7.197 CF.sub.3   H        0   CH.sub.3   CH 7.198 CF.sub.3   H        2   CH.sub.3   CH 7.199 OSO.sub.2 CH.sub.3 H        0   phenyl     CH 7.200 OSO.sub.2 CH.sub.3 H        2   phenyl     CH 7.201 OSO.sub.2 CH.sub.3 H        0   CSN(CH.sub.3).sub.2 CH 7.202 OSO.sub.2 CH.sub.3 H        0   pyrrolidino- CH thiocarbonyl 7.203 OSO.sub.2 CH.sub.3 H        0   CH.sub.3   CH 7.204 OSO.sub.2 CH.sub.3 H        2   CH.sub.3   CH 7.205 OSO.sub.2 C.sub.3 H.sub.7 n H        2   phenyl     CH 7.206 OSO.sub.2 C.sub.3 H.sub.7 n H        2   phenyl     CH 7.207 OSO.sub.2 C.sub.3 H.sub.7 n H        0   CSN(CH.sub.3).sub.2 CH 7.208 OSO.sub.2 C.sub.3 H.sub.7 n H        0   pyrrolidino- CH thiocarbonyl 7.209 OSO.sub.2 C.sub.3 H.sub.7 n H        2   CH.sub.3   CH 7.210 OSO.sub.2 C.sub.3 H.sub.7 n H        0   CH.sub.3   CH 7.211 SO.sub.2 N(CH.sub.3).sub.2 H        0   phenyl     CH 7.212 SO.sub.2 N(CH.sub.3).sub.2 H        2   phenyl     CH 7.213 SO.sub.2 N(CH.sub.3).sub.2 H        0   CSN(CH.sub.3).sub.2 CH 7.214 SO.sub.2 N(CH.sub.3).sub.2 H        0   pyrrolidino- CH thiocarbonyl 7.215 SO.sub.2 N(CH.sub.3).sub.2 H        0   CH.sub.3   CH 7.216 SO.sub.2 N(CH.sub.3).sub.2 H        2   CH.sub.3   CH 7.217 CH.sub.3   H        0   phenyl     CH 7.218 CH.sub.3   H        2   phenyl     CH 7.219 CH.sub.3   H        0   CSN(CH.sub.3).sub.2 CH 7.220 CH.sub.3   H        0   pyrrolidino- CH thiocarbonyl 7.221 CH.sub.3   H        0   CH.sub.3   CH 7.222 CH.sub.3   H        2   CH.sub.3   CH 7.223 SO.sub.2 CH.sub.3 H        0   phenyl     CH 7.224 SO.sub.2 CH.sub.3 H        2   phenyl     CH 7.225 SO.sub.2 CH.sub.3 H        0   CSN(CH.sub.3).sub.2 CH 7.226 SO.sub.2 CH.sub.3 H        0   pyrrolidino- CH thiocarbonyl 7.227 SO.sub.2 CH.sub.3 H        0   CH.sub.3   CH 7.228 SO.sub.2 CH.sub. 3 H        2   CH.sub.3   CH 7.229 CF.sub.3   H        2   .beta.-naphthyl CH153- 156.degree. dec. 7.230 2,6-Cl.sub.2 H        2   .beta.-naphthyl CH154- 158.degree. dec. 7.231 phenyl     H        2   CH.sub.3   CH166- 170.degree. dec. 7.232 phenyl     H        2   p-tolyl    CH156- 159.degree. dec. 7.233 phenyl     H        0   4-chlorophenyl CH161- 154.degree. 7.234 F          H        0   4-chlorophenyl CH126- 127.degree. 7.235 phenyl     H        0   CH.sub.2 COOCH.sub.3 CH127- 129.degree. 7.236 NO.sub.2   H        0   anilidocarbonyl- CH162- methyl     165.degree. (dec.) 7.237 2-Cl, 6-CH.sub.3 H        2   p-tolyl    CH150- 152.degree. (dec.) ______________________________________ ______________________________________ ##STR46## No   R.sup.1   m     R.sup.9   R.sup.3 m.p. (.degree.C.) ______________________________________ 8.001 COOCH.sub.3 0     p-tolyl   CH.sub.3 8.002 COOCH.sub.3 0     p-tolyl   OCH.sub.3 8.003 COOCH.sub.3 0     p-tolyl   OCHF.sub.2 8.004 COOCH.sub.3 2     p-tolyl   CH.sub.3 8.005 COOCH.sub.3 2     p-tolyl   OCH.sub.3 8.006 COOCH.sub.3 2     p-tolyl   OCHF.sub.2 8.007 COOCH.sub.3 0     CSN(CH.sub.3).sub.2 CH.sub.3 8.008 COOCH.sub.3 0     CSN(CH.sub.3).sub.2 OCH.sub.3 8.009 COOCH.sub.3 0     CSN(CH.sub.3).sub.2 OCHF.sub.2 8.010 COOCH.sub.3 2     ethyl     CH.sub.3 8.011 COOCH.sub.3 2     ethyl     OCH.sub.3 8.012 COOCH.sub.3 2     ethyl     OCHF.sub.2 8.013 COOCH.sub.3 0     4-chlorophenyl CH.sub.3 8.014 COOCH.sub.3 0     4-chlorophenyl OCHF.sub.2 8.015 COOCH.sub.3 0     4-chlorophenyl OCH.sub.3 8.016 COOCH.sub.3 2     4-chlorophenyl CH.sub.3 8.017 COOCH.sub.3 2     4-chlorophenyl OCHF.sub.2 8.018 COOCH.sub.3 2     4-chlorophenyl OCH.sub.3 8.019 COOCH.sub.3 0     pyrrolidino CH.sub.3 thiocarbonyl 8.020 COOCH.sub.3 0     pyrrolidino- OCH.sub.2 thiocarbonyl 8.021 COOCH.sub.3 0     pyrrolidino- OCHF.sub.2 thiocarbonyl 8.022 OCHF.sub.2 0     p-tolyl   CH.sub.3 8.023 OCHF.sub.2 0     p-tolyl   OCH.sub.3 8.024 OCHF.sub.2 0     p-tolyl   OCHF.sub.2 8.025 OCHF.sub.2 2     p-tolyl   CH.sub.3 154-158.degree. dec. 8.026 OCHF.sub.2 2     p-tolyl   OCH.sub.3 8.027 OCHF.sub.2 2     p-tolyl   OCHF.sub.2 8.028 OCHF.sub.2 0     CSN(CH.sub.3).sub.2 CH.sub.3 8.029 OCHF.sub.2 0     CSN(CH.sub.3).sub.2 OCH.sub.3 8.030 OCHF.sub.2 0     CSN(CH.sub.3).sub.2 OCHF.sub.2 8.031 OCHF.sub.2 2     ethyl     CH.sub.3 8.032 OCHF.sub.2 2     ethyl     OCH.sub.3 8.033 OCHF.sub.2 2     ethyl     OCHF.sub.2 8.034 OCHF.sub.2 0     4-chlorophenyl CH.sub.3 8.035 OCHF.sub.2 0     4-chlorophenyl OCHF.sub.2 8.036 OCHF.sub.2 0     4-chlorophenyl OCH.sub.3 8.037 OCHF.sub. 2 2     4-chlorophenyl CH.sub.3 8.038 OCHF.sub.2 2     4-chlorophenyl OCHF.sub.2 8.039 OCHF.sub.2 2     4-chlorophenyl OCH.sub.3 8.040 OCHF.sub.2 0     pyrrolidino CH.sub.3 thiocarbonyl 8.041 OCHF.sub.2 0     pyrrolidino- OCH.sub.2 thiocarbonyl 8.042 OCHF.sub.2 0     pyrrolidino- OCHF.sub.2 thiocarbonyl 8.043 Cl        0     p-tolyl   CH.sub.3 8.044 Cl        0     p-tolyl   OCH.sub.3 8.045 Cl        0     p-tolyl   OCHF.sub.2 8.046 Cl        2     p-tolyl   CH.sub.3 8.047 Cl        2     p-tolyl   OCH.sub.3 8.048 Cl        2     p-tolyl   OCHF.sub.2 8.049 Cl        0     CSN(CH.sub.3).sub.2 CH.sub.3 8.050 Cl        0     CSN(CH.sub.3).sub.2 OCH.sub.3 8.051 Cl        0     CSN(CH.sub.3).sub.2 OCHF.sub.2 8.052 Cl        2     ethyl     CH.sub.3 8.053 Cl        2     ethyl     OCH.sub.3 8.054 Cl        2     ethyl     OCHF.sub.2 8.055 Cl        0     4-chlorophenyl CH.sub.3 8.056 Cl        0     4-chlorophenyl OCHF.sub.2 8.057 Cl        0     4-chlorophenyl OCH.sub.3 8.058 Cl        2     4-chlorophenyl CH.sub.3 8.059 Cl        2     4-chlorophenyl OCHF.sub.2 8.060 Cl        2     4-chlorophenyl OCH.sub.3 8.061 Cl        0     pyrrolidino- CH.sub.3 thiocarbonyl 8.062 Cl        0     pyrrolidino- OCH.sub.2 thiocarbonyl 8.063 Cl        0     pyrrolidino- OCHF.sub.2 thiocarbonyl 8.064 NO.sub.2  0     p-tolyl   CH.sub.3 8.065 NO.sub.2  0     p-tolyl   OCH.sub.3 8.066 NO.sub.2  0     p-tolyl   OCHF.sub.2 8.067 NO.sub.2  2     p-tolyl   CH.sub.3 8.068 NO.sub.2  2     p-tolyl   OCH.sub.3 8.069 NO.sub.2  2     p-tolyl   OCHF.sub.2 8.070 NO.sub.2  0     CSN(CH.sub.3).sub.2 CH.sub.3 8.071 NO.sub.2  0     CSN(CH.sub.3).sub.2 OCH.sub.3 8.072 NO.sub.2  0     CSN(CH.sub.3).sub.2 OCHF.sub.2 8.073 NO.sub.2  2     ethyl     CH.sub.3 8.074 NO.sub.2  2     ethyl     OCH.sub.3 8.075 NO.sub.2  2     ethyl     OCHF.sub.2 8.076 NO.sub.2  0     4-chlorophenyl CH.sub.3 8.077 NO.sub.2  0     4-chlorophenyl OCHF.sub.2 8.078 NO.sub.2  0     4-chlorophenyl OCH.sub.3 8.079 NO.sub.2  2     4-chlorophenyl CH.sub.3 8.080 NO.sub.2  2     4-chlorophenyl OCHF.sub.2 8.081 NO.sub.2  2     4-chlorophenyl OCH.sub.3 8.082 NO.sub.2  0     pyrrolidino- CH.sub.3 thiocarbonyl 8.083 NO.sub.2  0     pyrrolidino- OCH.sub.2 thiocarbonyl 8.084 NO.sub.2  0     pyrrolidino- OCHF.sub.2 thiocarbonyl 8.085 COOCH.sub.3 0     CH.sub.3  CH.sub.3 8.086 COOCH.sub.3 0     CH.sub.3  OCH.sub.3 8.087 COOCH.sub.3 0     CH.sub.3  OCHF.sub.2 8.088 COOCH.sub.3 2     CH.sub.3  CH.sub.3 8.089 COOCH.sub.3 2     CH.sub.3  OCH.sub.3 8.090 COOCH.sub.3 2     CH.sub.3  OCHF.sub.2 8.091 OCHF.sub.2 0     CH.sub.3  CH.sub.3 8.092 OCHF.sub.2 0     CH.sub.3  OCHF.sub.2 8.093 OCHF.sub.2 0     CH.sub.3  OCH.sub.3 8.094 OCHF.sub.2 2     CH.sub.3  CH.sub.3 8.095 OCHF.sub.2 2     CH.sub.3  OCH.sub.3 8.096 OCHF.sub.2 2     CH.sub.3  OCHF.sub.2 8.097 NO.sub.2  2     CH.sub.2 COOH CH.sub.3 139-141.degree. (dec.) 8.098 OCH.sub.3 2     CH.sub.3  CH.sub.3 148.degree.(dec.) 8.099 CF.sub.3  2     CH.sub.3  CH.sub.3 159-160.degree. (dec.) ______________________________________ __________________________________________________________________________ ##STR47## No R.sup.1 m R.sup.9 R.sup.3 R.sup.4 E  m.p. (.degree.C.) __________________________________________________________________________ 9.001 COOCH.sub.3 0 pyrrolidino- CH.sub.2 OCH.sub.3 OCH.sub.3 CH thiocarbonyl 9.002 COOCH.sub.3 0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl 9.003 COOCH.sub.3 0 pyrrolidino- Cl     OCH.sub.3 CH thiocarbonyl 9.004 COOCH.sub.3 0 pyrrolidino- N(CH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl 9.005 COOCH.sub.3 0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl 9.006 COOCH.sub.3 0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl 9.007 COOCH.sub.3 0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl 9.008 COOCH.sub.3 0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl 9.009 COOCH.sub.3 0 dimethylthio- Cl     OCH.sub.3 CH carbamoyl 9.010 COOCH.sub.3 0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 CH carbamoyl 9.011 COOCH.sub.3 0 dimethylthio- CH(OCH.sub.3) OCH.sub.3 CH carbamoyl 9.012 COOCH.sub.3 0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.013 COOCH.sub.3 0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.014 COOCH.sub.3 0 benzoyl Cl     OCH.sub.3 N 9.015 COOCH.sub.3 0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.016 COOCH.sub.3 0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.017 COOCH.sub.3 0 benzoyl CH.sub.2 Cl OCH.sub.3 CH 9.018 COOCH.sub.3 0 acetyl  CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.019 COOCH.sub.3 0 acetyl  OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.020 COOCH.sub.3 0 acetyl  Cl     OCH.sub.3 N 9.021 COOCH.sub.3 0 acetyl  N(CH.sub.3).sub.2 OCH.sub.3 N 9.022 COOCH.sub.3 0 acetyl  CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.023 COOCH.sub.3 0 acetyl  CH.sub.2 Cl OCH.sub.3 CH 9.024 OCHF.sub.2 0 pyrrolidino- CH.sub.2 OCH.sub.3 OCH.sub.3 CH thiocarbonyl 9.025 OCHF.sub.2 0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl 9.026 OCHF.sub.2 0 pyrrolidino- Cl     OCH.sub.3 CH 143-144.degree. dec. thiocarbonyl 9.027 OCHF.sub.2 0 pyrrolidino- N(CH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl 9.028 OCHF.sub.2 0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl 9.029 OCHF.sub.2 0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl 9.030 OCHF.sub.2 0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl 9.031 OCHF.sub.2 0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl 9.032 OCHF.sub.2 0 dimethylthio- Cl     OCH.sub.3 N carbamoyl 9.033 OCHF.sub.2 0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 N carbamoyl 9.034 OCHF.sub.2 0 dimethylthio- CH(OCH.sub.3) OCH.sub.3 CH carbamoyl 9.035 OCHF.sub.2 0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub. 3 CH 9.036 OCHF.sub.2 0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.037 OCHF.sub.2 0 benzoyl Cl     OCH.sub.3 N 9.038 OCHF.sub.2 0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 CH 9.039 OCHF.sub.2 0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.040 OCHF.sub.2 0 benzoyl CH.sub.2 Cl OCH.sub.3 CH 9.041 OCHF.sub.2 0 acetyl  CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.042 OCHF.sub.2 0 acetyl  OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.043 OCHF.sub.2 0 acetyl  Cl     OCH.sub.3 CH 9.044 OCHF.sub.2 0 acetyl  N(CH.sub.3).sub.2 OCH.sub.3 N 9.045 OCHF.sub.2 0 acetyl  CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.046 OCHF.sub.2 0 acetyl  CH.sub.2 Cl OCH.sub.3 CH 9.047 Cl    0 pyrrolidino- CH.sub.2 OCH.sub.3 OCH.sub.3 CH thiocarbonyl 9.048 Cl    0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl 9.049 Cl    0 pyrrolidino- Cl     OCH.sub.3 CH 141-143.degree. dec. thiocarbonyl 9.050 Cl    0 pyrrolidino- N(CH.sub.3).sub.2 OCH.sub.3 N thiocarbonyl 9.051 Cl    0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl 9.052 Cl    0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl 9.053 Cl    0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl 9.054 Cl    0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl 9.055 Cl    0 dimethylthio- Cl     OCH.sub.3 CH carbamoyl 9.056 Cl    0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 CH carbamoyl 9.057 Cl    0 dimethylthio- CH(OCH.sub.3).sub.2 OCH.sub.3 CH carbamoyl 9.058 Cl    0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.059 Cl    0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.060 Cl    0 benzoyl Cl     OCH.sub.3 N 9.061 Cl    0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 CH 9.062 Cl    0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.063 Cl    0 benzoyl CH.sub.2 Cl OCH.sub.3 CH 9.064 Cl    0 acetyl  CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.065 Cl    0 acetyl  OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.066 Cl    0 acetyl  Cl     OCH.sub.3 CH 9.067 Cl    0 acetyl  N(CH.sub.3).sub.2 OCH.sub.3 N 9.068 Cl    0 acetyl  CH(OCH.sub.3).sub.2 OCH.sub. 3 CH 9.069 Cl    0 acetyl  CH.sub.2 Cl OCH.sub.3 CH 9.070 COOCH.sub.3 0 2-chlorophenyl CH.sub.2 CH.sub.3 CH 9.071 COOCH.sub.3 2 2-chlorophenyl CH.sub.2 CH.sub.3 OCH.sub.3 CH 9.072 COOCH.sub.3 0 2-chlorophenyl Cl     OCH.sub.3 N 9.073 COOCH.sub.3 2 2-chlorophenyl Cl     OCH.sub.3 CH 9.074 COOCH.sub.3 0 2-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.075 COOCH.sub.3 2 2-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 CH 9.076 COOCH.sub.3 0 CH.sub.2 CH.sub.3 Cl     OCH.sub.3 N 9.077 COOCH.sub.3 2 CH.sub.2 CH.sub.3 Cl     OCH.sub.3 CH 9.078 COOCH.sub.3 0 CH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.079 COOCH.sub.3 2 CH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.080 COOCH.sub.3 0 p-tolyl OCH.sub.3 Cl  CH 9.081 COOCH.sub.3 2 p-tolyl OCH.sub.3 Cl  N 9.082 COOCH.sub.3 0 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.083 COOCH.sub.3 2 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.084 OCHF.sub.2 0 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 9.085 OCHF.sub.2 2 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH 154-157.degree. dec. 9.086 COOCH.sub.3 0 methyl  CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.087 COOCH.sub.3 0 methyl  OCH.sub.2 CH.sub.3 OCH.sub.3 CH 9.088 COOCH.sub.3 0 methyl  Cl     OCH.sub.3 CH 9.089 COOCH.sub.3 0 methyl  N(CH.sub.3).sub.2 OCH.sub.3 CH 9.090 COOCH.sub.3 0 methyl  CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.091 COOCH.sub.3 0 methyl  CH.sub.2 Cl OCH.sub.3 CH 9.092 COOCH.sub.3 2 methyl  CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.093 COOCH.sub.3 2 methyl  OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.094 COOCH.sub.3 2 methyl  Cl     OCH.sub.3 N 9.095 COOCH.sub.3 2 methyl  N(CH.sub.3).sub.2 OCH.sub.3 N 9.096 COOCH.sub.3 2 methyl  CH(OCH.sub.3) OCH.sub.3 CH 9.097 COOCH.sub.3 0 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.098 COOCH.sub.3 0 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.099 COOCH.sub.3 0 4-chlorophenyl Cl     OCH.sub.3 N 9.100 COOCH.sub.3 0 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.101 COOCH.sub.3 0 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.102 COOCH.sub.3 0 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH 9.103 COOCH.sub.3 2 4-chlorophenyl CH.sub.2 OCH.sub. 3 CH.sub.3 CH 9.104 COOCH.sub.3 2 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.105 COOCH.sub.3 2 4-chlorophenyl Cl     OCH.sub.3 N 9.106 COOCH.sub.3 2 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.107 COOCH.sub.3 2 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.108 COOCH.sub.3 2 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH 9.109 OCHF.sub.2 0 methyl  CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.110 OCHF.sub.2 0 methyl  OCH.sub.2 CH.sub.3 OCH.sub.3 CH 9.111 OCHF.sub.2 0 methyl  Cl     OCH.sub.3 N 9.112 OCHF.sub.2 0 methyl  N(CH.sub.3).sub.2 OCH.sub.3 CH 9.113 OCHF.sub.2 0 methyl  CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.114 OCHF.sub.2 0 methyl  CH.sub.2 Cl OCH.sub.3 CH 9.115 OCHF.sub.2 2 methyl  CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.116 OCHF.sub.2 2 methyl  OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.117 OCHF.sub.2 2 methyl  Cl     OCH.sub.3 N 9.118 OCHF.sub.2 2 methyl  N(CH.sub.3).sub.2 OCH.sub.3 N 9.119 OCHF.sub.2 2 methyl  CH(OCH.sub.3) OCH.sub.3 CH 9.120 OCHF.sub.2 0 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.121 OCHF.sub.2 0 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.122 OCHF.sub.2 0 4-chlorophenyl Cl     OCH.sub.3 N 9.123 OCHF.sub.2 0 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.124 OCHF.sub.2 0 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.125 OCHF.sub.2 0 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH 9.126 OCHF.sub.2 2 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH 9.127 OCHF.sub.2 2 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH 9.128 OCHF.sub.2 2 4-chlorophenyl Cl     OCH.sub.3 N 9.129 OCHF.sub.2 2 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N 9.130 OCHF.sub.2 2 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH 9.131 OCHF.sub.2 2 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH 9.132 Cl    0 4-chlorophenyl Cl     OCH.sub.3 CH 142-144.degree. 9.133 Cl    2 4-chlorophenyl Cl     OCH.sub.3 CH 140-142.degree. dec. 9.134 COOC.sub.2 H.sub.5 0 p-tolyl Cl     OCH.sub.3 CH 9.135 COOC.sub.2 H.sub.5 2 p-tolyl Cl     OCH.sub.3 CH 9.136 COOCH.sub.3 0 2,4,5-tri- CH.sub.2 OCH.sub.3 OCH.sub.3 CH 128-130.degree. dec. chlorophenyl 9.137 COOCH.sub.3 0 p-tolyl N(CH.sub.3).sub.2 OCH.sub.3 N  138-140.degree. 9.138 F     0 CH.sub.2 COOCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 N  130-133.degree. 9.139 NO.sub.2 0 2,4,5-tri- CH.sub.2 OCH.sub.3 OCH.sub.3 CH 118-120.degree. chlorophenyl 9.140 Cl    0 CH.sub.2 COOCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 N  135-138.degree. 9.141 COOCH.sub.3 0 CH.sub.2 COOCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 N  145-148.degree. 9.142 CF.sub.3 2 CH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 N  171-175.degree. dec. __________________________________________________________________________ __________________________________________________________________________ ##STR48## No  R.sup.1 R.sup.6      R.sup.3 R.sup.4 E  m.p. (.degree.C.) __________________________________________________________________________ 10.001 COOCH.sub.3 benztriazol-1-yl CH.sub.3 CH.sub.3 CH 178-180.degree. 10.002 COOCH.sub.3 1,2,4-triazol-1-yl CH.sub.3 CH.sub.3 CH 164-167.degree. 10.003 COOCH.sub.3 2-methylbenzimidazol-1-yl CH.sub.3 CH.sub.3 CH 10.004 COOCH.sub.3 2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH 10.005 Cl    benztriazol-1-yl CH.sub.3 CH.sub.3 CH 122-128.degree. dec. 10.006 Cl    1,2,4-triazol-1-yl CH.sub.3 CH.sub.3 CH 152-157.degree. dec. 10.007 Cl    2-methylbenzimidazol-1-yl CH.sub.3 CH.sub.3 CH 10.008 Cl    2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH 10.009 OCHF.sub.2 benztriazol-1-yl CH.sub.3 CH.sub.3 CH 10.010 OCHF.sub.2 1,2,4-triazol-1-yl CH.sub.3 CH.sub.3 CH 10.011 OCHF.sub.2 2-methylbenzimidazol-1-yl CH.sub.3 CH.sub.3 CH 10.012 OCHF.sub.2 2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH 10.013 OCHF.sub.2 benztriazol-1-yl CH.sub.3 OCHF.sub.2 CH 109-111.degree. 10.014 COOCH.sub.3 benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.015 COOCH.sub.3 1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.016 COOCH.sub.3 2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.017 COOCH.sub.3 2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH 10.018 Cl    benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.019 Cl    1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.020 Cl    2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.021 Cl    2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH 10.022 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH 144-147.degree. 10.023 OCHF.sub.2 1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.024 OCHF.sub.2 2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.025 OCHF.sub.2 2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH 10.026 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH 10.027 COOCH.sub.3 benztriazol-1-yl OCH.sub.3 CH.sub.3 CH 10.028 COOCH.sub.3 1,2,4-triazol-1-yl OCH.sub.3 CH.sub.3 CH 10.029 COOCH.sub.3 2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH 10.030 COOCH.sub.3 2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH 10.031 Cl    benztriazol-1-yl OCH.sub.3 CH.sub.3 CH 10.032 Cl    1,2,4-triazol-1-yl OCH.sub.3 CH.sub.3 CH 10.033 Cl    2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH 10.034 Cl    2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH 10.035 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 CH.sub.3 CH 154-158.degree. 10.036 OCHF.sub.2 1,2,4-triazol-1-yl OCH.sub.3 CH.sub.3 CH 10.037 OCHF.sub.2 2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH 10.038 OCHF.sub.2 2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH 10.039 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 OCHF.sub.2 CH 10.040 2,6-Cl.sub.2 1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH 156-159.degree. 10.041 COOCH.sub.3 benztriazol-1-yl OCH.sub.3 CH.sub.2 OCH.sub.3 CH 157-160.degree. 10.042 Cl    5(6)-nitro-benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH 152-155.degree. (mixture of isomers) 10.043 F     5(6)-nitro-benztriazol-1-yl OCH.sub.3 CH.sub.3 CH 147-149.degree. (mixture of isomers) 10.044 2-Cl,6-CH.sub.3 5(6)-Nitro-benztriazol-1-yl OCH.sub.3 CH.sub.3 CH 131-134.degree. (mixture of isomers) __________________________________________________________________________ (a) Wettable powders (a)      (b)     (c) ______________________________________ Compound of formula I 20%      60%      0.5% sodium lignosulfonate 5%       5%      5% sodium laurylsulfate 3%       --      -- sodium diisobutylnaphthalenesulfonate --       6%      6% octylphenol polyethylene glycol ether --       2%      2% (7-8 moles of ethylene oxide) highly dispersed silicid acid 5%       27%     27% kaolin              67%      --      -- sodium chloride     --       --      59.5% ______________________________________

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration. (b) Emulsifiable concentrates (a)    (b) ______________________________________ Compound of formula I  10%    1% octylphenol polyethylene glycol ether 3%    3% (4-5 moles of ethylene oxide) calcium dodecylbenzenesulfonate 3%    3% castor oil polyglycol ether 4%    4% (36 moles of ethylene oxide) cyclohexanone          30%    10% xylene mixture         50%    79% ______________________________________

Emulsions of any required concentration can be obtained from this concentrate by dilution with water. (c) Dusts           (a)     (b) ______________________________________ Compound of formula I 0.1%    1% talcum              99.9%   -- kaolin              --      99% ______________________________________

Dusts which are ready for use are obtained by mixing the active ingredient with the carriers, and grinding the mixture in a suitable mill. (d) Extruder granulate (a)    (b) ______________________________________ Compound of formula I 10%    1% sodium lignosulfonate 2%    2% carboxymethylcellulose 1%    1% kaolin               87%    96% ______________________________________

The active ingredient is mixed and ground with the adjuvants, and the mixture is subsequently moistened with water. The mixture is extruded and then dried in a stream of air. (e) Coated granulate ______________________________________ Compound of formula 3% polyethylene glycol 200 2% kaolin             94% ______________________________________

The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner. (f) Suspension concentrate (a)     (b) ______________________________________ Compound of formula I  40%      5% ethylene glycol        10%     10% nonylphenol polyethylene glycol ether 6%      1% (15 moles of ethylene oxide) sodium lignosulfonate  10%      5% carboxymethylcellulose  1%      1% 37% aqueous formaldehyde solution 0.2%    0.2% silicone oil in the form of a 75% 0.8%    0.8% aqueous emulsion water                  32%     77% ______________________________________

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water. (g) Salt solution ______________________________________ Compound of formula I  5% isopropylamine         1% octylphenol polyethylene glycol ether 3% (78 moles of ethylene oxide) water                  91% ______________________________________

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm.sup.3, water-absorbing capacity: 0.565 l/l). After the non-adsorptive vermiculite has been saturated with an aqueous emulsion in deionised water which contains the test compound in a concentration of 70.8 ppm, seeds of the following plants are sown on the surface: Nasturtium officinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis. The pots are then kept in a climatic chamber at 20.degree. C., an illumination of about 20 lux and a relative humidity of 70%. During the germinating phase of 4 to 6 days, the pots are covered with light permeable material and watered with deionised water to increase the local humidity. After the 5th day, 0.5% of a commercial liquid fertiliser (Greenzit.RTM., ex Ciba-Geigy) is added to the water. The test is evaluated 12 days after sowing and the action on the plants is assessed according to the following rating:

Preemergence action:

Concentration of the test compound emulsion: 70.8 ppm Test plant Compound Nasturtium  Stellaria Agrostis Digitaria ______________________________________ 5.001   2           2        2        2 5.004   1           1        1        1 5.007   1           1        1        1 5.022   2           2        2        2 5.051   2           2        2        2 5.061   2           2        2        2 5.064   1           1        1        1 5.066   1           1        1        1 5.089   2           1        1        2 5.102   2           1        1        2 5.105   1           1        1        1 5.107   1           1        1        1 5.121   2           2        2        2 5.124   2           2        2        2 5.130   2           2        2        2 5.133   2           2        2        2 5.142   2           2        2        2 5.165   1           2        1        2 5.170   2           2        2        2 5.229   2           2        2        2 5.230   2           2        2        2 5.231   2           2        2        2 5.232   2           1        1        2 5.235   2           2        2        2 5.236   2           1        1        2 5.237   2           2        2        2 5.238   2           1        2        2 5.239   2           1        1        1 5.240   2           2        2        2 5.241   2           2        2        2 5.242   2           2        2        2 5.243   2           3        2        3 5.244   2           3        2        3 5.246   3           4        3        5 5.247   3           5        3        5 5.252   2           2        2        2 6.001   2           2        2        2 6.010   1           1        1        1 6.011   1           1        1        1 6.013   2           2        2        2 6.021   2           2        2        2 6.040   2           2        2        2 6.041   2           2        2        2 6.061   2           1        2        1 6.230   2           2        3        3 6.233   3           4        4        5 6.240   3           3        3        3 6.242   2           2        2        2 6.245   1           1        1        1 6.253   1           1        1        1 6.254   1           1        1        1 6.267   2           2        2        2 6.268   1           1        1        1 6.269   2           2        2        2 6.270   2           2        2        2 7.001   1           1        1        1 7.061   1           1        1        1 7.082   2           2        2        2 7.084   2           2        2        2 7.141   2           2        2        3 7.142   2           2        2        2 7.229   4           5        4        5 7.230   2           1        1        2 7.231   2           2        2        3 7.232   2           2        2        3 7.234   2           2        2        3 7.236   2           2        2        2 7.237   2           1        1        1 8.004   2           2        2        2 8.025   2           1        2        1 8.067   2           2        2        2 8.097   2           2        2        2 9.026   1           1        1        2 9.049   2           2        2        2 9.083   2           2        2        2 9.085   2           1        1        2 9.132   1           1        1        2 9.133   1           1        1        2 9.139   2           2        2        2 9.140   1           1        1        2 9.141   1           1        1        1 10.001  2           2        2        2 10.002  2           2        1        2 10.005  2           2        4        5 10.006  2           2        2        2 10.013  2           3        2        4 10.022  2           2        1        2 10.035  2           2        2        2 10.040  2           2        2        2 10.041  2           2        2        2 10.042  2           3        2        3 10.043  2           2        2        2 10.044  2           2        2        2 ______________________________________

The test plants (centrosema plumieri and centrosema pubescens) are reared until fully grown and then cut back to a height of 60 cm. The plants are sprayed 7 days later with an aqeuous emulsion of the test compound. The test plants are kept at 70% relative humidity and 6000 lux artificial light for 14 hours per day, at day temperatures of 27.degree. C. and night temperatures of 21.degree. C. The test is evaluated 4 weeks after application by assessing and weighing the new growth compared with controls and by determining the phytotoxicity.

In this test a marked reduction in new growth of the plants treated with compounds of the formula I is observed (less than 20% of the new growth of untreated control plants), without damage being caused to the test plants.

Soybeans of the "Hark" variety are sown in plastic containers in an earth/peat/sand mixture (6:3:1). The containers are put into a climatic chamber and the plants develop to the 5-6 trefoil leaf stage after about 5 weeks by optimum control of temperature, light, fertiliser addition, and watering. The plants are then sprayed with an aqueous mixture of a compound of the formula I until thoroughly wetted. The rate of application corresponds to 100 g a.i. per hectare. Evaluation is made about 5 weeks after application. Compared with untreated controls, the compounds of the formula I markedly increase the number and weight of the harvested siliques on the leading shoot.

Summar barley (Hordeum vulgare) and summer rye (Secale) are sown in sterilised soil in plastic beakers in a greenhouse and watered as required. The cereal shoots are treated about 21 days after sowing with an aqueous spray mixture of a compound of the formula I. The concentration corresponds to 100 g of active ingredient per hectare. Evaluation of the growth of the cereals is made 21 days after application. A comparison with untreated controls shows that the growth of cereal plants treated with compounds of the formula I is significantly reduced (60-90% of the controls) and that the diameter of the stalks has in some cases increased.

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylis glomerate and Cynodon dactylone are sown in plastic dishes filled with an earth/peat/sand mixture (6:3:1), in a greenhouse, and watered as required. The emergent grasses are cut back weekly to a height of 4 cm, and about 50 days after sowing and 1 day after the last cut are sprayed with an aqueous spray mixture of a compound of the formula I. The concentration of test compound corresponds to a rate of application of up to 100 g a.i. per hectare. The growth of the grasses is evaluated 21 days after application. The compounds of formula I effect a reduction in new growth in the range of 10-30% in comparison with untreated controls.

To determine the stimulation of root growth, seeds which have been dressed with 45-500 mg of active ingredient per kg of seeds as well as untreated seeds for use as controls are propagated in plastic cylinders of 5 cm diameter and 30 cm in heigth. 10 seeds are propagated in each cylinder. The cylinders are kept in climatic chambers under controlled conditions. Evaluation of the test is made 10 days after sowing and after carefully washing off the soil. The length and dry weight of the roots are determined and compared with the results obtained with untreated seeds.

Compared with untreated seedlings, wheat seeds treated with 100 and 200 mg of active ingredient per kg of seeds exhibited an approximately 10% increase in length and weight.

## Claims

1. An N-sulfonyl-N'-triazinylurea of the formula ##STR49## wherein E is nitrogen, haloalkoxy, NR.sup.10 R.sup.11, --OSO.sub.2 R.sup.8, --COR.sup.8 or --SO.sub.2 NR.sup.10 R.sup.11, haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, NH.sub.2, substituted by halogen, or C.sub.1 -C.sub.4 alkyl, from among, 1,2,4-triazinyl, imidazolyl, indolyl, benzimidazolyl and benzotriazolyl, which is bound via the nitrogen atom, wherein the benzene ring is unsubstituted or substituted by one or more identical or different members selected from the groups consisting of nitro, halogen or C.sub.1 -C.sub.4 alkyl, -C.sub.4 haloalkyl, C.sub.4 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 cyanoalkyl, C.sub.1 -C.sub.4 alkyl--NR.sup.9 R.sup.10, benzyl or benzyl which is substituted by halogen, halogen, C.sub.1 -C.sub.4 alkoxy, carboxyl, C.sub.1 -C.sub.4 alkoxycarbonyl or R.sup.9 is --CONR.sup.10 R.sup.11, or is phenyl, benzyl or napthyl, each of which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of halogen, nitro, carboxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy, and in an --SR.sup.9 radical, or R.sup.9 can also be a radical selected from --CZ--C.sub.1 -C.sub.4 alkyl, --CZO--C.sub.1 -C.sub.4 alkyl, --CZNR.sup.10 R.sup.11, --CZ-phenyl, CZ-benzyl or CZ-naphthyl, wherein the phenyl rings are unsubstituted or substituted as indicated above, -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 cyanoalkyl or one of R.sup.10 and R.sup.11 is C.sub.1 -C.sub.4 alkoxy or C.sub.2 -C.sub.4 alkoxyalkyl, phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted by halogen, nitro, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkyl or attached form the pyrrolidino or piperidino or ring, m is 0, 1 or 2.

2. An N-sulfonyl-N'-triazinylurea according to claim 1 wherein Z is oxygen and R.sup.2 and R.sup.5 are hydrogen.

3. An N-sulfonyl-N'-triazinylurea according to claim 1 of the formula ##STR50## wherein R.sup.1, R.sup.3, R.sup.4 and R.sup.6 have the meaning given in claim 1.

4. An N-sulfonyl-N'-triazinylurea according to claim 1 of the formula ##STR51## wherein m is 0 or 2 and R.sup.1 R.sup.3, R.sup.4 and R.sup.9 have the meaning given in claim 1.

5. An N-sulfonyl-N'-triazinylurea according to claim 4 wherein haloalkoxy or C.sub.1 -C.sub.4 alkoxycarbonyl and halogen, C.sub.1 -C.sub.4 alkoxycarboxy, C.sub.1 -C.sub.4 alkoxycarbonyl or R.sup.9 is --CONR.sup.10 R.sup.11 or phenyl, benzyl or naphthyl, each of which is unsubstituted or substituted by one or more identical or different members selected from the groups consisting of halogen, nitro C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy and in an --SR.sup.9 group R.sup.9 can also be a radical selected from --CZC.sub.1 -C.sub.4 alkyl, --CZOC.sub.1 -C.sub.4 alkyl, --CZNR.sup.10 R.sup.11, --CZphenyl, --CZbenzyl or --CZnaphthyl, wherein the phenyl rings are unsubstituted or substituted as indicated above, attached form the pyrrolidino or piperidino ring and Z is oxygen or sulfur.

6. N-(Methoxycarbonylphenylsulfonyl)-N'-para-tolylthiomethyl-N'(4-dimethyla mino-6-methoxy-1,3,5-triazin-2-yl)urea according to claim 1.

7. N-(2-Fluorophenylsulfonyl)-N'-methoxycarbonylmethythiomet hyl-N'-(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)urea according to claim 1.

8. N-(Chl orophenylsulfonyl)-N'-methoxycarbonylmethylthiomethyl-N'-(4-dimethylamino-6 -methoxy-1,3,5-triazin-2-yl)urea according to claim 1.

9. N-(2-Methoxycarbonylphenylsulfonyl)-N'-methoxycarbo nylmethylthiomethyl-N'-(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)urea according to claim 1.

10. N-(2-Trifluormethy lphenylsulfonyl)-N'-methylsulfonylmethyl-N'-(4-dimethylamino-6-methoxy-1,3, 5-triazin-2-yl)urea according to claim 1.

11. A herbicidal and plant-growth inhibiting composition, which comprises a herbicidal or plant-growth-inhibitingly effective amount of a substituted N-phenylsulfonyl-N'-triazinylurea according to claim 1, or salt thereof together with an inert carrier and/or other adjuvants usual in agricultural compositions.

12. A method of controlling undesired plant growth, which comprises application of a herbicidally effective amount of a compound of claim 1, or of a composition containing such a compound to the undesired plants or the locus thereof.

13. A method for inhibiting plant growth, which comprises application of a growth inhibitingly effective amount of a compound of claim 1, or of a composition containing such a compound to the plants.

14. A method of selecting controlling weeds pre- or postemergence in crops of useful plants, which method comprises application of a herbicidally effective amount of a compound according to claim 1, or a composition containing such a compound to a cultivated area in which plant seeds have been sown.