Herbicidal sulfonylureas

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 triazin-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.,
X is oxygen, sulfur, --NR.sup.7, --N.dbd.CR.sup.7, --CH.dbd.CH-- or ##STR4## Y is oxygen or an S(O).sub.m radical, m is 0 or an integer from 1 to 2,
Z is oxygen or sulfur,
R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alk kenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, 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,
R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or nitro,
R.sup.3 and R.sup.4, each independently of the other, are hydrogen, 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,
R.sup.6 is an --S(O).sub.m R.sup.9 radical or a 5- to 7-membered 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,
R.sup.7 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.5 -C.sub.6 6cycloalkyl, 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,
R.sup.8 is C.sub.1 -C.sub.4 alkoxy or has the same meaning as R.sup.7 but is not hydrogen,
R.sup.9 is a C.sub.1 -C.sub.4 alkyl radical which can be substituted by 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 substtiuted 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,
R.sup.10 and R.sup.11, each independently of the other, are hydrogen, 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 44211, 44807 and 44808, and also in UK patent applications 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 sdubstituted 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
Z is an oxygen atom,
the ##STR8## radical is a phenyl radical which is substituted in the ortho-position by R.sup.1,
R.sup.6 is an --S(O).sub.m R.sup.8 radical,
R.sup.6 is a 5- to 7-membered heterocycle which is bound through the nitrogen atom and may contain further hetero atoms in the ring, and may be fused to a benzene ring and may be unsubstituted 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. ##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. ##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. ##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. ##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. ##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. ##STR23##
This schema 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 oxidized to give the corresponding sulfinyl or sulfonyl compound of formula Ib by an oxidation similar to that described after scheme III. ##STR24##
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 reside 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 encapsulation 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. Exampls 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 concentratesactive 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%Dustsactive ingredient: 0.1 to 10%, preferably 0.1 to 1%solid carrier: 99.9 to 90%, preferably 99.9 to 99%Suspension concentratesactive 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 powdersactive 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%Granulatesactive 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.

EXAMPLE 1
Preparation of 2-[(4-chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine (intermediate) ##STR25##
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:
TABLE 1__________________________________________________________________________ ##STR26## (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 N-phenylcarbamoyl- 161-163.degree. methyl1.19 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-Chlor- CH 2-carboxylphenyl 193-195.degree. phenyl (dec.)1.27 CH.sub.3 CH.sub.3 H CH 2-carboxylphenyl 226-228.degree. (dec.)__________________________________________________________________________
EXAMPLE 2
Preparation of 4-dimethylamino-6-methoxy-2-(4-tolylsulfonyl)methylamino-1,3,5-triazine ##STR27##
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-4-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).
EXAMPLE 3
Preparation of 4,6-dimethyl-2-(4-tolylsulfonylmethylamino)pyrimidine ##STR28##
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 minute 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:
TABLE 2__________________________________________________________________________ ##STR29## (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.3 145-1482.02 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-tolyl2.09 Cl CH.sub.3 H 2 CH p-tolyl2.10 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-chlorophenyl2.12 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-methoxy- 135-136.degree. carbonylbenzyl2.23 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-difluoro- 137-138.degree. methoxyphenyl2.25 OCH.sub.3 OCH.sub.3 H 2 CH 2,4,6-tri- 131-133.degree. methylphenyl2.26 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.)__________________________________________________________________________
EXAMPLE 4
Preparation of 4,6-dimethyl-2-(morpholin-4-ylthiocarbonylthiomethylamino)pyrimidine ##STR30##
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:
TABLE 3______________________________________ ##STR31## m.p.No. R.sup.3 R.sup.4 E R.sup.9 (.degree.C.)______________________________________3.01 CH.sub.3 CH.sub.3 CH pyrrolidinothiocarbonyl 116- 118.degree.3.02 CH.sub.3 CH.sub.3 CH morpholinothiocarbonyl 119- 121.degree.3.03 Cl OCH.sub.3 CH pyrrolidinothiocarbonyl 136- 139.degree.3.04 CH.sub.3 CH.sub.3 CH azepinylthiocarbonyl 90- 92.degree.3.05 CH.sub.3 CH.sub.3 CH methoxythiocarbonyl3.06 CH.sub.3 CH.sub.3 CH dimethylthiocarbamoyl 105- 115.degree.3.07 CH.sub.3 CH.sub.3 CH acetyl3.08 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.______________________________________
EXAMPLE 5
Preparation of 4-methoxy-6-methyl-2-(1,2,4-triazol-1-ylmethylamino)pyrimidine ##STR32##
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.
EXAMPLE 6
Preparation of 2-[(2,6-dichlorophenyl)-(1,2,4-triazol-1-yl)methyl]-amino-4,6-dimethylpyrimidine ##STR33##
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.
EXAMPLE 7
Preparation of 2-(benztriazol-1-ylmethylamino)-4-dimethylamino-6-methoxy-1,3,5-triazine ##STR34##
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.
EXAMPLE 8
Preparation of 4,6-dimethyl-2-[2-methylbenzimidizol-1-yl)methylamino]pyrimidine ##STR35##
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 acetete/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:
TABLE 4__________________________________________________________________________ ##STR36##__________________________________________________________________________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.__________________________________________________________________________No. R.sup.3 R.sup.4 R.sup.5 E R.sup.8 m.p. (.degree.C.)__________________________________________________________________________4.14 CH.sub.3 OCH.sub.3 H CH 5(6)-nitro-benz- 190-193.degree.* triazol-1-yl4.15 OCH.sub.3 OCH.sub.3 H CH 5(6)-nitro-benz- 173-175.degree.* triazol-1-yl4.16 CH.sub.3 OCH.sub.3 H CH 5(6)-chlorobenz- 156-168.degree.* triazol-1-yl4.17 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 4aH-carbazol-1-yl 153-155.degree.4.19 CH.sub.3 CH.sub.3 H CH 2-methyl-benz- 207-212.degree. imidazol-1-yl4.20 CH.sub.3 CH.sub.3 H CH 2,3-dimethylindol-1-yl4.21 CH.sub.3 OCH.sub.3 H N 2,3-dimethylindol-1-yl4.22 OCHF.sub.2 CH.sub.3 H CH 2,3-dimethylindol-1-yl4.23 CH.sub.3 CH.sub.3 H CH 2,4,5-tribromimidazol-1-yl4.24 CH.sub.3 CH.sub.3 H CH 2,4,5-tribromimidazol-1-yl4.25 N(CH.sub.3).sub.2 OCH.sub.3 H N 2,4,5-tribromimidazol-1-yl4.26 CH.sub.3 OCH.sub.3 H CH pyrazol-1-yl4.27 OCHF.sub.2 CH.sub.3 H CH pyrazol-1-yl4.28 Cl OCH.sub.3 H N pyrazol-1-yl4.29 CH.sub.3 OCH.sub.3 CH.sub.3 CH 1,2,4-triazol-1-yl__________________________________________________________________________ *mixture of isomers
EXAMPLE 9
Preparation of N-2-chlorophenylsulfonyl-N'-(4-chlorophenylthiomethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR37##
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 acetetate/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.
EXAMPLE 10
Preparation of N-(2-difluoromethoxyphenylsulfonyl)-N'-(p-tolylulfonylmethyl)-N'-(-4-difluorom ethoxy-6-methylpyrimidin-2-yl)urea ##STR38##
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.).
EXAMPLE 11
Preparation of N-(2-chlorophenylsulfonyl)-N'-(pyrrolidinothiocarbonylthiomethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR39##
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 at 131.degree.-133.degree. C. with decomposition.
EXAMPLE 12
Preparation of N-(2-chlorophenylsulfonyl)-N'-(1,2,4-triazol-1-ylmethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR40##
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.
EXAMPLE 13
Preparation of N-(2-(2-methoxycarbonylphenylsulfonyl-N'-(benztriazol-1-methyl)-N'-4,6-dimethylpyrimidin-2-yl)urea ##STR41##
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:
TABLE 5__________________________________________________________________________ ##STR42##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 CH5.003 COOCH.sub.3 H 2 4-chlorophenyl CH5.004 COOCH.sub.3 H 0 4-chlorophenyl CH 141-144.degree.5.005 COOCH.sub.3 H 0 acetyl CH5.006 COOCH.sub.3 H 0 benzoyl CH5.007 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 CH5.009 COOCH.sub.3 H 2 CH(CH.sub.3).sub.2 CH5.010 COOCH.sub.3 H 2 benzyl CH5.011 COOCH.sub.3 H 2 phenyl CH5.012 COOCH.sub.3 H 0 phenyl CH5.013 COOCH.sub.3 H 2 4-bromophenyl CH5.014 COOCH.sub.3 H 0 4-bromophenyl CH5.015 COOCH.sub.3 H 2 2-chlorophenyl CH5.016 COOCH.sub.3 H 0 2-chlorophenyl CH5.017 COOCH.sub.3 H 0 CH.sub.3 CH5.018 COOCH.sub.3 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH5.019 COOCH.sub.3 H 0 CH(CH.sub.3).sub.2 CH5.020 COOCH.sub.3 H 0 benzyl CH5.021 COOCH.sub.3 H 2 .beta.-naphthyl CH5.022 COOCH.sub.3 H 0 .beta.-naphthyl CH 178-183.degree. (dec.)5.023 COOCH.sub.3 H 2 1,2,4-trichloro- CH phenyl5.024 COOCH.sub.3 H 0 1,2,4-trichloro- CH phenyl5.025 COOCH.sub.3 H 2 .alpha.-naphthyl CH5.026 COOCH.sub.3 H 2 .alpha.-naphthyl CH5.027 COOCH.sub.3 H 0 CH.sub.2 COOCH.sub.3 CH5.028 COOCH.sub.3 H 2 4-fluorophenyl CH5.029 COOCH.sub.3 H 0 4-fluorophenyl CH5.030 COOCH.sub.3 H 0 4-nitrophenyl CH5.031 COOCH.sub.3 H 0 4-nitrophenyl CH5.032 COOCH.sub.3 H 2 2-nitrophenyl CH5.033 COOCH.sub.3 H 0 2-nitrophenyl CH5.034 COOCH.sub.3 H 2 2-trifluoromethyl CH5.035 COOCH.sub.3 H 0 2-trifluoromethyl CH5.036 COOCH.sub.3 H 2 4-methoxyphenyl CH5.037 COOCH.sub.3 H 0 4-methoxyphenyl CH5.038 COOCH.sub.3 H 2 2-methoxyphenyl CH5.039 COOCH.sub.3 H 0 2-methoxyphenyl CH5.040 COOCH.sub.3 H 2 2,4,6-trimethyl- CH phenyl5.041 COOCH.sub.3 H 0 2,4,6-trimethyl- CH phenyl5.042 COOCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.043 COOCH.sub.3 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH5.044 COOCH.sub.3 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH5.045 COOCH.sub.3 H 0 pyrrolidinothio- CH carbonyl5.046 COOCH.sub.3 H 0 piperidinothio- CH carbonyl5.047 COOCH.sub.3 H 0 anilidoacetyl CH5.048 COOCH.sub.3 H 0 2,4-dichlorophenyl CH5.049 COOCH.sub.3 H 2 2,4-dichlorophenyl CH5.050 COOCH.sub.3 H 0 CH.sub.2 COOH CH5.051 COOCH.sub.3 H 0 CH.sub.2 COO CH.sub.3 CH 154-156.degree.5.052 COOCH.sub.3 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH5.053 COOCH.sub.3 H 0 4-chlorophenyl N5.054 COOCH.sub.3 H 0 p-tolyl N5.055 COOCH.sub.3 furyl-2- 0 2-hydroxy- CH carbonylphenyl5.056 COOCH.sub.3 furyl-2- 0 2-methoxy- CH carbonylphenyl5.057 COOCH.sub.3 furyl-2- 0 phenyl CH5.058 COOCH.sub.3 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl5.059 COOCH.sub.3 4-chloro- 0 phenyl CH phenyl5.060 COOCH.sub.3 CH.sub.3 0 4-chlorophenyl CH5.061 OCHF.sub.2 H 2 p-tolyl CH 152-157.degree. (dec.)5.062 OCHF.sub.2 H 0 p-tolyl CH5.063 OCHF.sub.2 H 2 4-chlorophenyl CH5.064 OCHF.sub.2 H 0 4-chlorophenyl CH 109-111.degree.5.065 OCHF.sub.2 H 0 acetyl CH5.066 OCHF.sub.2 H 0 benzoyl CH 155-158.degree. dec.5.067 OCHF.sub.2 H 2 CH.sub.3 CH5.068 OCHF.sub.2 H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH5.069 OCHF.sub.2 H 2 CH(CH.sub.3).sub.2 CH5.070 OCHF.sub.2 H 2 benzyl CH5.071 OCHF.sub.2 H 2 phenyl CH5.072 OCHF.sub.2 H 0 phenyl CH5.073 OCHF.sub.2 H 2 4-bromophenyl CH5.074 OCHF.sub.2 H 0 4-bromophenyl CH5.075 OCHF.sub.2 H 2 2-chlorophenyl CH5.076 OCHF.sub.2 H 0 2-chlorophenyl CH5.077 OCHF.sub.2 H 0 CH.sub.3 CH5.078 OCHF.sub.2 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH5.079 OCHF.sub.2 H 0 CH(CH.sub.3).sub.2 CH5.080 OCHF.sub.2 H 0 benzyl CH5.081 OCHF.sub.2 H 2 .beta.-naphthyl CH5.082 OCHF.sub.2 H 0 .beta.-naphthyl CH 162-164.degree.5.083 OCHF.sub.2 H 2 1,2,4-trichloro- CH phenyl5.084 OCHF.sub.2 H 0 1,2,4-trichloro- CH phenyl5.085 OCHF.sub.2 H 2 .alpha.-naphthyl CH5.086 OCHF.sub.2 H 2 .alpha.-naphthyl CH5.087 OCHF.sub.2 H 0 CH.sub.2 COOCH.sub.3 CH5.088 OCHF.sub.2 H 2 4-fluorophenyl CH5.089 OCHF.sub.2 H 0 4-fluorophenyl CH 125-127.degree.5.090 OCHF.sub.2 H 0 4-nitrophenyl CH5.091 OCHF.sub.2 H 0 4-nitrophenyl CH5.092 OCHF.sub.2 H 2 2-nitrophenyl CH5.093 OCHF.sub.2 H 0 2-nitrophenyl CH5.094 OCHF.sub.2 H 2 2-trifluoromethyl CH5.095 OCHF.sub.2 H 0 2-trifluoromethyl CH5.096 OCHF.sub.2 H 2 4-methoxyphenyl CH5.097 OCHF.sub.2 H 0 4-methoxyphenyl CH5.098 OCHF.sub.2 H 2 2-methoxyphenyl CH5.099 OCHF.sub.2 H 0 2-methoxyphenyl CH5.100 OCHF.sub.2 H 2 2,4,6-trimethyl- CH phenyl5.101 OCHF.sub.2 H 0 2,4,6-trimethyl- CH phenyl5.102 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 CH5.104 OCHF.sub.2 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH5.105 OCHF.sub.2 H 0 pyrrolidinothio- CH 136-139.degree. carbonyl dec.5.106 OCHF.sub.2 H 0 piperidinothio- CH carbonyl5.107 OCHF.sub.2 H 0 N-phenylcarbamoyl- CH 110-112.degree. methyl5.108 OCHF.sub.2 H 0 2,4-dichlorophenyl CH5.109 OCHF.sub.2 H 2 2,4-dichlorophenyl CH5.110 OCHF.sub.2 H 0 CH.sub.2 COOH CH5.111 OCHF.sub.2 H 0 CH.sub.2 COO CH.sub.3 CH5.112 OCHF.sub.2 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH5.113 OCHF.sub.2 H 0 4-chlorophenyl N5.114 OCHF.sub.2 H 0 p-tolyl N5.115 OCHF.sub.2 Furyl-2- 0 2-hydroxy- CH carbonylphenyl5.116 OCHF.sub.2 Furyl-2- 0 2-methoxy- CH carbonylphenyl5.117 OCHF.sub.2 Furyl-2- 0 phenyl CH5.118 OCHF.sub.2 4-Chlor- 0 2-hydroxy- CH phenyl carbonylphenyl5.119 OCHF.sub.2 4-Chlor- 0 phenyl CH phenyl5.120 OCHF.sub.2 CH.sub.3 0 4-chlorophenyl CH5.121 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 CH5.124 Cl H 0 4-chlorophenyl CH 132-135.degree. dec.5.125 Cl H 0 acetyl CH5.126 Cl H 0 benzoyl CH5.127 Cl H 2 CH.sub.3 CH5.128 Cl H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH5.129 Cl H 2 CH(CH.sub.3).sub.2 CH5.130 Cl H 2 benzyl CH 146-147.degree. (dec.)5.131 Cl H 2 phenyl CH5.132 Cl H 0 phenyl CH5.133 Cl H 2 4-bromophenyl CH 150-153.degree. (dec.)5.134 Cl H 0 4-bromophenyl CH5.135 Cl H 2 2-chlorophenyl CH5.136 Cl H 0 2-chlorophenyl CH5.137 Cl H 0 CH.sub.3 CH5.138 Cl H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH5.139 Cl H 0 CH(CH.sub.3).sub.2 CH5.140 Cl H 0 benzyl CH5.141 Cl H 2 .beta.-naphthyl CH5.142 Cl H 0 .beta.-naphthyl CH 156-158.degree.5.143 Cl H 2 1,2,4-trichloro- CH phenyl5.144 Cl H 0 1,2,4-trichloro- CH phenyl5.145 Cl H 2 .alpha.-naphthyl CH5.146 Cl H 2 .alpha.-naphthyl CH5.147 Cl H 0 CH.sub.2 COOCH.sub.3 CH5.148 Cl H 2 4-fluorophenyl CH5.149 Cl H 0 4-fluorophenyl CH5.150 Cl H 0 4-nitrophenyl CH5.151 Cl H 0 4-nitrophenyl CH5.152 Cl H 2 2-nitrophenyl CH5.153 Cl H 0 2-nitrophenyl CH5.154 Cl H 2 2-trifluoromethyl CH5.155 Cl H 0 2-trifluoromethyl CH5.156 Cl H 2 4-methoxyphenyl CH5.157 Cl H 0 4-methoxyphenyl CH5.158 Cl H 2 2-methoxyphenyl CH5.159 Cl H 0 2-methoxyphenyl CH5.160 Cl H 2 2,4,6-trimethyl- CH phenyl5.161 Cl H 0 2,4,6-trimethyl- CH phenyl5.162 Cl H 0 CSN(CH.sub.3).sub.2 CH5.163 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH5.164 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH5.165 Cl H 0 pyrrolidinothio- CH 131-133.degree. carbonyl dec.5.166 Cl H 0 piperidinothio- CH carbonyl5.167 Cl H 0 N-phenylcarbamoyl- CH 110-112.degree. methyl5.168 Cl H 0 2,4-dichlorophenyl CH5.169 Cl H 2 2,4-dichlorophenyl CH5.170 Cl H 0 CH.sub.2 COOH CH 123-125.degree. (dec.)5.171 Cl H 0 CH.sub.2 COO CH.sub.3 CH5.172 Cl H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH5.173 Cl H 0 4-chlorophenyl N5.174 Cl H 0 p-tolyl N5.175 Cl furyl-2- 0 2-hydroxy- CH carbonylphenyl5.176 Cl furyl-2- 0 2-methoxy- CH carbonylphenyl5.177 Cl furyl-2- 0 phenyl CH5.178 Cl 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl5.179 Cl 4-chloro- 0 phenyl CH phenyl5.180 Cl CH.sub.3 0 4-chlorophenyl CH5.181 OCH.sub.3 H 0 phenyl CH5.182 OCH.sub.3 H 2 phenyl CH5.183 OCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.184 OCH.sub.3 H 0 pyrrolidinothio- CH carbonyl5.185 OCH.sub.3 H 0 CH.sub.3 CH5.186 OCH.sub.3 H 2 CH.sub.3 CH5.187 NO.sub.2 H 0 phenyl CH5.188 NO.sub.2 H 2 phenyl CH5.189 NO.sub.2 H 0 CSN(CH.sub. 3).sub.2 CH5.190 NO.sub.2 H 0 pyrrolidinothio- CH carbonyl5.191 NO.sub.2 H 0 CH.sub.3 CH5.192 NO.sub.2 H 2 CH.sub.3 CH5.193 CF.sub.3 H 0 phenyl CH5.194 CF.sub.3 H 2 phenyl CH5.195 CF.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.196 CF.sub.3 H 0 pyrrolidino- CH thiocarbonyl5.197 CF.sub.3 H 0 CH.sub.3 CH5.198 CF.sub.3 H 2 CH.sub.3 CH5.199 OSO.sub.2 CH.sub.3 H 0 phenyl CH5.200 OSO.sub.2 CH.sub.3 H 2 phenyl CH5.201 OSO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.202 OSO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl5.203 OSO.sub.2 CH.sub.3 H 0 CH.sub.3 CH5.204 OSO.sub.2 CH.sub.3 H 2 CH.sub.3 CH5.205 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH5.206 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH5.207 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CSN(CH.sub.3).sub.2 CH5.208 OSO.sub.2 C.sub.3 H.sub.7 n H 0 pyrrolidino- CH thiocarbonyl5.209 OSO.sub.2 C.sub.3 H.sub.7 n H 2 CH.sub.3 CH5.210 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CH.sub.3 CH5.211 SO.sub.2 N(CH.sub.3).sub.2 H 0 phenyl CH5.212 SO.sub.2 N(CH.sub.3).sub.2 H 2 phenyl CH5.213 SO.sub.2 N(CH.sub.3).sub.2 H 0 CSN(CH.sub.3).sub.2 CH5.214 SO.sub.2 N(CH.sub.3).sub.2 H 0 pyrrolidino- CH thiocarbonyl5.215 SO.sub.2 N(CH.sub.3).sub.2 H 0 CH.sub.3 CH5.216 SO.sub.2 N(CH.sub.3).sub.2 H 2 CH.sub.3 CH5.217 CH.sub.3 H 0 phenyl CH5.218 CH.sub.3 H 2 phenyl CH5.219 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.220 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl5.221 CH.sub.3 H 0 CH.sub.3 CH5.222 CH.sub.3 H 2 CH.sub.3 CH5.223 SO.sub.2 CH.sub.3 H 0 phenyl CH5.224 SO.sub.2 CH.sub.3 H 2 phenyl CH5.225 SO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH5.226 SO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl5.227 SO.sub.2 CH.sub.3 H 0 CH.sub.3 CH5.228 SO.sub.2 CH.sub.3 H 2 CH.sub.3 CH5.229 CH.sub.3 H 2 p-tolyl CH 148-150.degree. dec.5.230 CH.sub.3 H 0 morpholino- CH 145-146.degree. thiocarbonyl dec.5.231 OCHF.sub.2 H 0 morpholino- CH 132-134.degree. thiocarbonyl dec.5.232 OCHF.sub.2 H 0 4-fluorophenyl CH 125-127.degree.5.233 COOCH.sub.3 H 0 4-fluorophenyl CH5.234 COOCH.sub.3 H 2 4-fluorophenyl CH5.235 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 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 dec.5.247 phenyl H 0 CH(CH.sub.3)COOH CH 150-152.degree. dec.5.248 Cl H 2 phenyl N5.249 Cl H 2 p-tolyl N5.250 COOCH.sub.3 H 2 CH.sub.3 N5.251 OCHF.sub.2 H 2 p-tolyl N5.252 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.__________________________________________________________________________
TABLE 6__________________________________________________________________________ ##STR43##__________________________________________________________________________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 CH6.003 COOCH.sub.3 H 2 4-chlorophenyl CH6.004 COOCH.sub.3 H 0 4-chlorophenyl CH6.005 COOCH.sub.3 H 0 acetyl CH6.006 COOCH.sub.3 H 0 benzoyl CH6.007 COOCH.sub.3 H 2 CH.sub.3 CH6.008 COOCH.sub.3 H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.009 COOCH.sub.3 H 2 CH(CH.sub.3).sub.2 CH6.010 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 CH6.013 COOCH.sub.3 H 2 4-bromophenyl CH 134-135.degree. (dec.)6.014 COOCH.sub.3 H 0 4-bromophenyl CH6.015 COOCH.sub.3 H 2 2-chlorophenyl CH6.016 COOCH.sub.3 H 0 2-chlorophenyl CH6.017 COOCH.sub.3 H 0 CH.sub.3 CH6.018 COOCH.sub.3 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.019 COOCH.sub.3 H 0 CH(CH.sub.3).sub.2 CH6.020 COOCH.sub.3 H 0 benzyl CH6.021 COOCH.sub.3 H 2 .beta.-naphthyl CH 140-141.degree. (dec.)6.022 COOCH.sub.3 H 0 .beta.-naphtyl CH6.023 COOCH.sub.3 H 2 1,2,4-trichloro- CH phenyl6.024 COOCH.sub.3 H 0 1,2,4-trichloro- CH phenyl6.025 COOCH.sub.3 H 2 .alpha.-naphthyl CH6.026 COOCH.sub.3 H 2 .alpha.-naphthyl CH6.027 COOCH.sub.3 H 0 CH.sub.2 COOCH.sub.3 CH6.028 COOCH.sub.3 H 2 4-fluorophenyl CH6.029 COOCH.sub.3 H 0 4-fluorophenyl CH6.030 COOCH.sub.3 H 0 4-nitrophenyl CH6.031 COOCH.sub.3 H 0 4-nitrophenyl CH6.032 COOCH.sub.3 H 2 2-nitrophenyl CH6.033 COOCH.sub.3 H 0 2-nitrophenyl CH6.034 COOCH.sub.3 H 2 2-trifluoromethyl- CH phenyl6.035 COOCH.sub.3 H 0 2-trifluoromethyl- CH phenyl6.036 COOCH.sub.3 H 2 4-methoxyphenyl CH6.037 COOCH.sub.3 H 0 4-methoxyphenyl CH6.038 COOCH.sub.3 H 2 2-methoxyphenyl CH6.039 COOCH.sub.3 H 0 2-methoxyphenyl CH6.040 COOCH.sub.3 H 2 2,4,6-trimethyl- CH 133-134.degree. (dec.) phenyl6.041 COOCH.sub.3 H 0 2,4,6-trimethyl- CH phenyl6.042 COOCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.043 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 N6.045 COOCH.sub.3 H 0 pyrrolidinothio- CH carbonyl6.046 COOCH.sub.3 H 0 piperidinothio- CH carbonyl6.047 COOCH.sub.3 H 0 N-phenylcarbamoyl- CH methyl6.048 COOCH.sub.3 H 0 2,4-dichlorophenyl CH6.049 COOCH.sub.3 H 2 2,4-dichlorophenyl CH6.050 COOCH.sub.3 H 0 CH.sub.2 COOH CH6.051 COOCH.sub.3 H 0 CH.sub.2 COOCH.sub. 3 CH6.052 COOCH.sub.3 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH6.053 COOCH.sub.3 H 0 4-Chlorophenyl N6.054 COOCH.sub.3 H 0 p-tolyl N6.055 COOCH.sub.3 furyl-2- 0 2-hydroxy- CH carbonylphenyl6.056 COOCH.sub.3 furyl-2- 0 2-methoxy- CH carbonylphenyl6.057 COOCH.sub.3 furyl-2- 0 phenyl CH6.058 COOCH.sub.3 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl6.059 COOCH.sub.3 4-chloro- 0 phenyl CH phenyl6.060 COOCH.sub.3 CH.sub.3 0 4-chlorophenyl CH6.061 OCHF.sub.2 H 2 p-tolyl CH 142-143.degree.6.062 OCHF.sub.2 H 0 p-tolyl CH6.063 OCHF.sub.2 H 2 4-chlorophenyl CH6.064 OCHF.sub.2 H 0 4-chlorophenyl CH6.065 OCHF.sub.2 H 0 acetyl CH6.066 OCHF.sub.2 H 0 benzoyl CH6.067 OCHF.sub.2 H 2 CH.sub.3 CH6.068 OCHF.sub.2 H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.069 OCHF.sub.2 H 2 CH(CH.sub.3).sub.2 CH6.070 OCHF.sub.2 H 2 benzyl CH6.071 OCHF.sub.2 H 2 phenyl CH6.072 OCHF.sub.2 H 0 phenyl CH6.073 OCHF.sub.2 H 2 4-bromophenyl CH6.074 OCHF.sub.2 H 0 4-bromophenyl CH6.075 OCHF.sub.2 H 2 2-chlorophenyl CH6.076 OCHF.sub.2 H 0 2-chlorophenyl CH6.077 OCHF.sub.2 H 0 CH.sub.3 CH6.078 OCHF.sub.2 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.079 OCHF.sub.2 H 0 CH(CH.sub.3).sub.2 CH6.080 OCHF.sub.2 H 0 benzyl CH6.081 OCHF.sub.2 H 2 .beta.-naphthyl CH6.082 OCHF.sub.2 H 0 .beta.-naphthyl CH6.083 OCHF.sub.2 H 2 1,2,4-trichloro- CH phenyl6.084 OCHF.sub.2 H 0 1,2,4-trichloro- CH phenyl6.085 OCHF.sub.2 H 2 .alpha.-naphthyl CH6.086 OCHF.sub.2 H 2 .alpha.-naphthyl CH6.087 OCHF.sub.2 H 0 CH.sub.2 COOCH.sub.3 CH6.088 OCHF.sub.2 H 2 4-fluorophenyl CH6.089 OCHF.sub.2 H 0 4-fluorophenyl CH6.090 OCHF.sub.2 H 0 4-nitrophenyl CH6.091 OCHF.sub.2 H 0 4-nitrophenyl CH6.092 OCHF.sub.2 H 2 2-nitrophenyl CH6.093 OCHF.sub.2 H 0 2-nitrophenyl CH6.094 OCHF.sub.2 H 2 2-trifluoromethyl CH6.095 OCHF.sub.2 H 0 2-trifluoromethyl CH6.096 OCHF.sub.2 H 2 4-methoxyphenyl CH6.097 OCHF.sub.2 H 0 4-methoxyphenyl CH6.098 OCHF.sub.2 H 2 2-methoxyphenyl CH6.099 OCHF.sub.2 H 0 2-methoxyphenyl CH6.100 OCHF.sub.2 H 2 2,4,6-trimethyl- CH phenyl6.101 OCHF.sub. 2 H 0 2,4,6-trimethyl- CH phenyl6.102 OCHF.sub.2 H 0 CSN(CH.sub.3).sub.2 CH6.103 OCHF.sub.2 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH6.104 OCHF.sub.2 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH6.105 OCHF.sub.2 H 0 pyrrolidinothio- CH carbonyl6.106 OCHF.sub.2 H 0 piperidinothio- CH carbonyl6.107 OCHF.sub.2 H 0 N-phenylcarbamoyl- CH methyl6.108 OCHF.sub.2 H 0 2,4-dichlorophenyl CH6.109 OCHF.sub.2 H 2 2,4-dichlorophenyl CH6.110 OCHF.sub.2 H 0 CH.sub.2 COOH CH6.111 OCHF.sub.2 H 0 CH.sub.2 COOCH.sub.3 CH6.112 OCHF.sub.2 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH6.113 OCHF.sub.2 H 0 4-chlorophenyl N6.114 OCHF.sub.2 H 0 p-tolyl N6.115 OCHF.sub.2 furyl-2- 0 2-hydroxy- CH carbonylphenyl6.116 OCHF.sub.2 furyl-2- 0 2-methoxy- CH carbonylphenyl6.117 OCHF.sub.2 furyl-2- 0 phenyl CH6.118 OCHF.sub.2 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl6.119 OCHF.sub.2 4-chloro- 0 phenyl CH phenyl6.120 OCHF.sub.2 CH.sub.3 0 4-chlorophenyl CH6.121 Cl H 2 p-tolyl CH6.122 Cl H 0 p-tolyl CH6.123 Cl H 2 4-chlorophenyl CH6.124 Cl H 0 4-chlorophenyl CH6.125 Cl H 0 acetyl CH6.126 Cl H 0 benzoyl CH6.127 Cl H 2 CH.sub.3 CH6.128 Cl H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.129 Cl H 2 CH(CH.sub.3).sub.2 CH6.130 Cl H 2 benzyl CH6.131 Cl H 2 phenyl CH6.132 Cl H 0 phenyl CH6.133 Cl H 2 4-bromophenyl CH6.134 Cl H 0 4-bromophenyl CH6.135 Cl H 2 2-chlorophenyl CH6.136 Cl H 0 2-chlorophenyl CH6.137 Cl H 0 CH.sub.3 CH6.138 Cl H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH6.139 Cl H 0 CH(CH.sub.3).sub.2 CH6.140 Cl H 0 benzyl CH6.141 Cl H 2 .beta.-naphthyl CH6.142 Cl H 0 .beta.-naphthyl CH6.143 Cl H 2 1,2,4-trichloro- CH phenyl6.144 Cl H 0 1,2,4-trichloro- CH phenyl6.145 Cl H 2 .alpha.-naphthyl CH6.146 Cl H 2 .alpha.-naphthyl CH6.147 Cl H 0 CH.sub.2 COOCH.sub.3 CH6.148 Cl H 2 4-fluorophenyl CH6.149 Cl H 0 4-fluorophenyl CH6.150 Cl H 0 4-nitrophenyl CH6.151 Cl H 0 4-nitrophenyl CH6.152 Cl H 2 2-nitrophenyl CH6.153 Cl H 0 2-nitrophenyl CH6.154 Cl H 2 2-trifluoromethyl CH6.155 Cl H 0 2-trifluoromethyl CH6.156 Cl H 2 4-methoxyphenyl CH6.157 Cl H 0 4-methoxyphenyl CH6.158 Cl H 2 2-methoxyphenyl CH6.159 Cl H 0 2-methoxyphenyl CH6.160 Cl H 2 2,4,6-trimethyl- CH phenyl6.161 Cl H 0 2,4,6-trimethyl- CH phenyl6.162 Cl H 0 CSN(CH.sub.3).sub.2 CH6.163 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH6.164 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH6.165 Cl H 0 pyrrolidinothio- CH carbonyl6.166 Cl H 0 piperidinothio- CH carbonyl6.167 Cl H 0 N-phenylcarbamoyl- CH methyl6.168 Cl H 0 2,4-dichlorophenyl CH6.169 Cl H 2 2,4-dichlorophenyl CH6.170 Cl H 0 CH.sub.2 COOH CH6.171 Cl H 0 CH.sub.2 COOCH.sub.3 CH6.172 Cl H 0 CH.sub.2 CON(CH.sub.3).sub. 2 CH6.173 Cl H 0 4-chlorophenyl N6.174 Cl H 0 p-tolyl N6.175 Cl furyl-2- 0 2-hydroxy- CH carbonylphenyl6.176 Cl furyl-2- 0 2-methoxy- CH carbonylphenyl6.177 Cl furyl-2- 0 phenyl CH6.178 Cl 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl6.179 Cl 4-chloro- 0 phenyl CH phenyl6.180 Cl CH.sub.3 0 4-chlorophenyl CH6.181 OCH.sub.3 H 0 phenyl CH6.182 OCH.sub.3 H 2 phenyl CH6.183 OCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.184 OCH.sub.3 H 0 pyrrolidinothio- CH carbonyl6.185 OCH.sub.3 H 0 CH.sub.3 CH6.186 OCH.sub.3 H 2 CH.sub.3 CH6.187 NO.sub.2 H 0 phenyl CH6.188 NO.sub.2 H 2 phenyl CH6.189 NO.sub.2 H 0 CSN(CH.sub.3).sub.2 CH6.190 NO.sub.2 H 0 pyrrolidinothio- CH carbonyl6.191 NO.sub.2 H 0 CH.sub.3 CH6.192 NO.sub.2 H 2 CH.sub.3 CH6.193 CF.sub.3 H 0 phenyl CH6.194 CF.sub.3 H 2 phenyl CH6.195 CF.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.196 CF.sub.3 H 0 pyrrolidino- CH thiocarbonyl6.197 CF.sub.3 H 0 CH.sub.3 CH6.198 CF.sub.3 H 2 CH.sub.3 CH6.199 OSO.sub.2 CH.sub.3 H 0 phenyl CH6.200 OSO.sub.2 CH.sub.3 H 2 phenyl CH6.201 OSO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.202 OSO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl6.203 OSO.sub.2 CH.sub.3 H 0 CH.sub.3 CH6.204 OSO.sub.2 CH.sub.3 H 2 CH.sub.3 CH6.205 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH6.206 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH6.207 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CSN(CH.sub.3).sub.2 CH6.208 OSO.sub.2 C.sub.3 H.sub.7 n H 0 pyrrolidino- CH thiocarbonyl6.209 OSO.sub.2 C.sub.3 H.sub.7 n H 2 CH.sub.3 CH6.210 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CH.sub.3 CH6.211 SO.sub.2 N(CH.sub.3).sub.2 H 0 phenyl CH6.212 SO.sub.2 N(CH.sub.3).sub.2 H 2 phenyl CH6.213 SO.sub.2 N(CH.sub.3).sub.2 H 0 CSN(CH.sub.3).sub.2 CH6.214 SO.sub.2 N(CH.sub.3).sub.2 H 0 pyrrolidino- CH thiocarbonyl6.215 SO.sub.2 N(CH.sub.3).sub.2 H 0 CH.sub.3 CH6.216 SO.sub.2 N(CH.sub.3).sub.2 H 2 CH.sub.3 CH6.217 CH.sub.3 H 0 phenyl CH6.218 CH.sub.3 H 2 phenyl CH6.219 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.220 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl6.221 CH.sub.3 H 0 CH.sub.3 CH6.222 CH.sub.3 H 2 CH.sub.3 CH6.223 SO.sub.2 CH.sub.3 H 0 phenyl CH6.224 SO.sub.2 CH.sub.3 H 2 phenyl CH6.225 SO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH6.226 SO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl6.227 SO.sub.2 CH.sub.3 H 0 CH.sub.3 CH6.228 SO.sub.2 CH.sub.3 H 2 CH.sub.3 CH6.229 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 N6.232 COOCH.sub.3 H 2 phenyl N6.233 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 CH6.235 OCF.sub.2 CHF.sub.2 H 2 CH.sub.3 CH6.236 OCF.sub.2 CHF.sub.2 H 2 phenyl CH6.237 OCF.sub.2 CHF.sub.2 H 2 4-chlorophenyl CH6.238 OCF.sub.2 CHF.sub.2 H 2 .beta.-naphthyl CH6.239 F H 0 4-chlorophenyl CH6.240 F H 0 .beta.-naphthyl CH 158-154.degree.6.241 F H 2 .beta.-naphthyl CH6.242 COOCH.sub.3 H 2 2-methoxy- CH 66-67.degree. carbonylbenzyl6.243 COOCH.sub.3 H 2 C.sub.3 H.sub.7 n CH6.244 COOCH.sub.3 H 2 C.sub.2 H.sub.5 CH6.245 COOCH.sub.3 H 2 2-difluoromethoxy- CH 145-147.degree. phenyl6.246 COOCH.sub.3 H 2 3,4-dichlorophenyl CH6.247 COOCH.sub.3 H 2 3,5-dichlorophenyl CH6.248 COOCH.sub.3 H 2 3-chlorophenyl CH6.249 COOCH.sub.3 H 2 2-difluoromethyl- CH thiophenyl6.250 COOCH.sub.3 H 2 3-trifluoromethyl- CH phenyl6.251 COOCH.sub.3 H 2 2,5-dimethyl- CH phenyl6.252 COOC.sub.2 H.sub.5 H 2 CH.sub.3 CH6.253 COOC.sub.2 H.sub.5 H 2 C.sub.3 H.sub.7 n CH6.254 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 CH6.257 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 CH6.260 NO.sub.2 H 2 .beta.-naphthyl CH6.261 NO.sub.2 H 2 C.sub.2 H.sub.5 CH6.262 NO.sub.2 H 2 C.sub.3 H.sub.7 n CH6.263 NO.sub.2 H 2 benzyl CH6.264 NO.sub.2 H 2 2-methoxy- CH carbonylbenzyl6.265 NO.sub.2 H 2 4-methoxy- CH phenyl6.266 NO.sub.2 H 2 2-difluoro- CH methoxyphenyl6.267 NO.sub.2 H 2 mesityl CH6.268 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 CH6.274 OSO.sub.2 N(CH.sub.3).sub.2 2 p-tolyl CH6.275 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.)__________________________________________________________________________
TABLE 7__________________________________________________________________________ ##STR44##No R.sup.1 R.sup.5 m R.sup.9 E m.p.(.degree.C.)__________________________________________________________________________7.001 COOCH.sub.3 H 2 p-tolyl CH 153-158.degree. dec.7.002 COOCH.sub.3 H 0 p-tolyl CH7.003 COOCH.sub.3 H 2 4-chlorophenyl CH7.004 COOCH.sub.3 H 0 4-chlorophenyl CH7.005 COOCH.sub.3 H 0 acetyl CH7.006 COOCH.sub.3 H 0 benzoyl CH7.007 COOCH.sub.3 H 2 CH.sub.3 CH7.008 COOCH.sub.3 H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.009 COOCH.sub.3 H 2 CH(CH.sub.3).sub.2 CH7.010 COOCH.sub.3 H 2 benzyl CH7.011 COOCH.sub.3 H 2 phenyl CH7.012 COOCH.sub.3 H 0 phenyl CH7.013 COOCH.sub.3 H 2 4-bromophenyl CH7.014 COOCH.sub.3 H 0 4-bromophenyl CH7.015 COOCH.sub.3 H 2 2-chlorophenyl CH7.016 COOCH.sub.3 H 0 2-chlorophenyl CH7.017 COOCH.sub.3 H 0 CH.sub.3 CH7.018 COOCH.sub.3 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.019 COOCH.sub.3 H 0 CH(CH.sub.3).sub.2 CH7.020 COOCH.sub.3 H 0 benzyl CH7.021 COOCH.sub.3 H 2 .beta.-naphthyl CH7.022 COOCH.sub.3 H 0 .beta.-naphthyl CH7.023 COOCH.sub.3 H 2 1,2,4-trichloro- CH phenyl7.024 COOCH.sub.3 H 0 1,2,4-trichloro- CH phenyl7.025 COOCH.sub.3 H 2 .alpha.-naphthyl CH7.026 COOCH.sub.3 H 2 .alpha.-naphthyl CH7.027 COOCH.sub.3 H 0 CH.sub.2 COOCH.sub.3 CH7.028 COOCH.sub.3 H 2 4-fluorophenyl CH7.029 COOCH.sub.3 H 0 4-fluorophenyl CH7.030 COOCH.sub.3 H 0 4-nitrophenyl CH7.031 COOCH.sub.3 H 0 4-nitrophenyl CH7.032 COOCH.sub.3 H 2 2-nitorphenyl CH7.033 COOCH.sub.3 H 0 2-nitrophenyl CH7.034 COOCH.sub.3 H 2 2-trifluoromethyl CH7.035 COOCH.sub.3 H 0 2-trifluoromethyl CH7.036 COOCH.sub.3 H 2 4-methoxyphenyl CH7.037 COOCH.sub.3 H 0 4-methoxyphenyl CH7.038 COOCH.sub.3 H 2 2-methoxyphenyl CH7.039 COOCH.sub.3 H 0 2-methoxyphenyl CH7.040 COOCH.sub.3 H 2 2,4,6-trimethyl- CH phenyl7.041 COOCH.sub.3 H 0 2,4,6-trimethyl- CH phenyl7.042 COOCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.043 COOCH.sub.3 H 0 CSN(CH.sub.3 CH.sub.3).sub.2 CH7.044 COOCH.sub.3 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH7.045 COOCH.sub.3 H 0 pyrrolidinothio- CH carbonyl7.046 COOCH.sub.3 H 0 piperidinothio- CH carbonyl7.047 COOCH.sub.3 H 0 N-phenylcarbamoyl- CH methyl7.048 COOCH.sub.3 H 0 2,4-dichlorophenyl CH7.049 COOCH.sub.3 H 2 2,4-dichlorophenyl CH7.050 COOCH.sub.3 H 0 CH.sub.2 COOH CH7.051 COOCH.sub.3 H 0 CH.sub.2 COOCH.sub.3 CH7.052 COOCH.sub.3 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH7.053 COOCH.sub.3 H 0 4-chlorophenyl N7.054 COOCH.sub.3 H 0 p-tolyl N7.055 COOCH.sub.3 furyl-2- 0 2-hydroxy- CH carbonylphenyl7.056 COOCH.sub.3 furyl-2- 0 2-methoxy- CH carbonylphenyl7.057 COOCH.sub.3 furyl-2- 0 phenyl CH7.058 COOCH.sub.3 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl7.059 COOCH.sub.3 4-chloro- 0 phenyl CH phenyl7.060 COOCH.sub.3 CH.sub.3 0 4-chlorophenyl CH7.061 OCHF.sub.2 H 2 p-tolyl CH 146-150.degree.7.062 OCHF.sub.2 H 0 p-tolyl CH7.063 OCHF.sub.2 H 2 4-chlorophenyl CH7.064 OCHF.sub.2 H 0 4-chlorophenyl CH7.065 OCHF.sub.2 H 0 acetyl CH7.066 OCHF.sub.2 H 0 benzoyl CH7.067 OCHF.sub.2 H 2 CH.sub.3 N7.068 OCHF.sub.2 H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.069 OCHF.sub.2 H 2 CH(CH.sub.3).sub.2 CH7.070 OCHF.sub.2 H 2 benzyl CH7.071 OCHF.sub.2 H 2 phenyl CH7.072 OCHF.sub.2 H 0 phenyl CH7.073 OCHF.sub.2 H 2 4-bromophenyl CH7.074 OCHF.sub.2 H 0 4-bromophenyl CH7.075 OCHF.sub.2 H 2 2-chlorophenyl CH7.076 OCHF.sub.2 H 0 2-chlorophenyl CH7.077 OCHF.sub.2 H 0 CH.sub.3 N7.078 OCHF.sub.2 H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.079 OCHF.sub.2 H 0 CH(CH.sub.3).sub.2 CH7.080 OCHF.sub.2 H 0 benzyl CH7.081 OCHF.sub.2 H 2 .beta.-naphthyl CH7.082 OCHF.sub.2 H 0 .beta.-naphthyl CH 162-164.degree.7.083 OCHF.sub.2 H 2 1,2,4-trichloro- CH phenyl7.084 OCHF.sub.2 H 0 2,4,5-trichloro- CH 104-107.degree. phenyl7.085 OCHF.sub.2 H 2 .alpha.-naphthyl CH7.086 OCHF.sub.2 H 2 .alpha.-naphthyl CH7.087 OCHF.sub.2 H 0 CH.sub.2 COOCH.sub.3 CH7.088 OCHF.sub.2 H 2 4-fluorophenyl CH7.089 OCHF.sub.2 H 0 4-fluorophenyl CH7.090 OCHF.sub.2 H 0 4-nitrophenyl CH7.091 OCHF.sub.2 H 0 4-nitrophenyl CH7.092 OCHF.sub.2 H 2 2-nitrophenyl CH7.093 OCHF.sub.2 H 0 2-nitrophenyl CH7.094 OCHF.sub.2 H 2 2-trifluoromethyl CH7.095 OCHF.sub.2 H 0 2-trifluoromethyl CH7.096 OCHF.sub.2 H 2 4-methoxyphenyl CH7.097 OCHF.sub.2 H 0 4-methoxyphenyl CH7.098 OCHF.sub.2 H 2 2-methoxyphenyl CH7.099 OCHF.sub.2 H 0 2-methoxyphenyl CH7.100 OCHF.sub.2 H 2 2,4,6-trimethyl- CH phenyl7.101 OCHF.sub.2 H 0 2,4,6-trimethyl- CH phenyl7.102 OCHF.sub.2 H 0 CSN(CH.sub.3).sub.2 CH7.103 OCHF.sub.2 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH7.104 OCHF.sub.2 H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH7.105 OCHF.sub.2 H 0 pyrrolidinothio- CH carbonyl7.106 OCHF.sub.2 H 0 piperidinothio- CH carbonyl7.107 OCHF.sub.2 H 0 N-phenylcarbamoyl- CH methyl7.108 OCHF.sub.2 H 0 2,4-dichlorophenyl CH7.109 OCHF.sub.2 H 2 2,4-dichlorophenyl CH7.110 OCHF.sub.2 H 0 CH.sub.2 COOH CH7.111 OCHF.sub.2 H 0 CH.sub.2 COOCH.sub.3 CH7.112 OCHF.sub.2 H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH7.113 OCHF.sub.2 H 0 4-Chlorophenyl N7.114 OCHF.sub.2 H 0 p-tolyl N7.115 OCHF.sub.2 furyl-2- 0 2-hydroxy- CH carbonylphenyl7.116 OCHF.sub.2 furyl-2- 0 2-methoxy- CH carbonylphenyl7.117 OCHF.sub.2 furyl-2- 0 phenyl CH7.118 OCHF.sub.2 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl7.119 OCHF.sub.2 4-chloro- 0 phenyl CH phenyl7.120 OCHF.sub.2 CH.sub.3 0 4-chlorophenyl CH7.121 Cl H 2 p-tolyl CH7.122 Cl H 0 p-tolyl CH7.123 Cl H 2 4-chlorophenyl CH7.124 Cl H 0 4-chlorophenyl CH7.125 Cl H 0 acetyl CH7.126 Cl H 0 benzoyl CH7.127 Cl H 2 CH.sub.3 CH7.128 Cl H 2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.129 Cl H 2 CH(CH.sub.3).sub.2 CH7.130 Cl H 2 benzyl CH7.131 Cl H 2 phenyl CH7.132 Cl H 0 phenyl CH7.133 Cl H 2 4-bromophenyl CH7.134 Cl H 0 4-bromophenyl CH7.135 Cl H 2 2-chlorophenyl CH7.136 Cl H 0 2-chloropehnyl CH7.137 Cl H 0 CH.sub.3 CH7.138 Cl H 0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH7.139 Cl H 0 CH(CH.sub.3).sub.2 CH7.140 Cl H 0 benzyl CH7.141 Cl H 2 .beta.-naphthyl CH7.142 Cl H 0 .beta.-naphthyl CH 156-158.degree. dec.7.143 Cl H 2 1,2,4-trichloro- CH phenyl7.144 Cl H 0 1,2,4-trichloro- CH phenyl7.145 Cl H 2 .alpha.-naphthyl CH7.146 Cl H 2 .alpha.-naphthyl CH7.147 Cl H 0 CH.sub.2 COOCH.sub.3 CH7.148 Cl H 2 4-fluorophenyl CH7.149 Cl H 0 4-fluorophenyl CH7.150 Cl H 0 4-nitrophenyl CH7.151 Cl H 0 4-nitrophenyl CH7.152 Cl H 2 2-nitrophenyl CH7.153 Cl H 0 2-nitrophenyl CH7.154 Cl H 2 2-trifluoromethyl CH7.155 Cl H 0 2-trifluoromethyl CH7.156 Cl H 2 4-methoxyphenyl CH7.157 Cl H 0 4-methoxyphenyl CH7.158 Cl H 2 2-methoxyphenyl CH7.159 Cl H 0 2-methoxyphenyl CH7.160 Cl H 2 2,4,6-trimethyl- CH phenyl7.161 Cl H 0 2,4,6-trimethyl- CH phenyl7.162 Cl H 0 CSN(CH.sub.3).sub.2 CH7.163 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH7.164 Cl H 0 CSN(CH.sub.2 CH.sub.3).sub.2 CH7.165 Cl H 0 pyrrolidinothio- CH carbonyl7.166 Cl H 0 piperidinothio- CH carbonyl7.167 Cl H 0 N-phenylcarbamoyl- CH methyl7.168 Cl H 0 2,4-dichlorophenyl CH7.169 Cl H 2 2,4-dichlorophenyl CH7.170 Cl H 0 CH.sub.2 COOH CH7.171 Cl H 0 CH.sub.2 COOCH.sub.3 CH7.172 Cl H 0 CH.sub.2 CON(CH.sub.3).sub.2 CH7.173 Cl H 0 4-chlorophenyl N7.174 Cl H 0 p-tolyl N7.175 Cl furyl-2- 0 2-hydroxy- CH carbonylphenyl7.176 Cl furyl-2- 0 2-methoxy- CH carbonylphenyl7.177 Cl furyl-2- 0 phenyl CH7.178 Cl 4-chloro- 0 2-hydroxy- CH phenyl carbonylphenyl7.179 Cl 4-chloro- 0 phenyl CH phenyl7.180 Cl CH.sub.3 0 4-chlorophenyl CH7.181 OCH.sub.3 H 0 phenyl CH7.182 OCH.sub.3 H 2 phenyl CH7.183 OCH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.184 OCH.sub.3 H 0 pyrrolidinothio- CH carbonyl7.185 OCH.sub.3 H 0 CH.sub.3 CH7.186 OCH.sub.3 H 2 CH.sub.3 CH7.187 NO.sub.2 H 0 phenyl CH7.188 NO.sub.2 H 2 phenyl CH7.189 NO.sub.2 H 0 CSN(CH.sub.3).sub.2 CH7.190 NO.sub.2 H 0 pyrrolidinothio- CH carbonyl7.191 NO.sub.2 H 0 CH.sub.3 CH7.192 NO.sub.2 H 2 CH.sub.3 CH7.193 CF.sub.3 H 0 phenyl CH7.194 CF.sub.3 H 2 phenyl CH7.195 CF.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.196 CF.sub.3 H 0 pyrrolidino- CH thiocarbonyl7.197 CF.sub.3 H 0 CH.sub.3 CH7.198 CF.sub.3 H 2 CH.sub.3 CH7.199 OSO.sub.2 CH.sub.3 H 0 phenyl CH7.200 OSO.sub.2 CH.sub.3 H 2 phenyl CH7.201 OSO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.202 OSO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl7.203 OSO.sub.2 CH.sub.3 H 0 CH.sub.3 CH7.204 OSO.sub.2 CH.sub.3 H 2 CH.sub.3 CH7.205 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH7.206 OSO.sub.2 C.sub.3 H.sub.7 n H 2 phenyl CH7.207 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CSN(CH.sub.3).sub.2 CH7.208 OSO.sub.2 C.sub.3 H.sub.7 n H 0 pyrrolidino- CH thiocarbonyl7.209 OSO.sub.2 C.sub.3 H.sub.7 n H 2 CH.sub.3 CH7.210 OSO.sub.2 C.sub.3 H.sub.7 n H 0 CH.sub.3 CH7.211 SO.sub.2 N(CH.sub.3).sub.2 H 0 phenyl CH7.212 SO.sub.2 N(CH.sub.3).sub.2 H 2 phenyl CH7.213 SO.sub.2 N(CH.sub.3).sub.2 H 0 CSN(CH.sub. 3).sub.2 CH7.214 SO.sub.2 N(CH.sub.3).sub.2 H 0 pyrrolidino- CH thiocarbonyl7.215 SO.sub.2 N(CH.sub.3).sub.2 H 0 CH.sub.3 CH7.216 SO.sub.2 N(CH.sub.3).sub.2 H 2 CH.sub.3 CH7.217 CH.sub.3 H 0 phenyl CH7.218 CH.sub.3 H 2 phenyl CH7.219 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.220 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl7.221 CH.sub.3 H 0 CH.sub.3 CH7.222 CH.sub.3 H 2 CH.sub.3 CH7.223 SO.sub.2 CH.sub.3 H 0 phenyl CH7.224 SO.sub.2 CH.sub.3 H 2 phenyl CH7.225 SO.sub.2 CH.sub.3 H 0 CSN(CH.sub.3).sub.2 CH7.226 SO.sub.2 CH.sub.3 H 0 pyrrolidino- CH thiocarbonyl7.227 SO.sub.2 CH.sub.3 H 0 CH.sub.3 CH7.228 SO.sub.2 CH.sub.3 H 2 CH.sub.3 CH7.229 CF.sub.3 H 2 .beta.-naphthyl CH 153-156.degree. dec.7.230 2,6-Cl.sub.2 H 2 .beta.-naphthyl CH 154-158.degree. dec.7.231 phenyl H 2 CH.sub.3 CH 166-170.degree. dec.7.232 phenyl H 2 p-tolyl CH 156-159.degree. dec.7.233 phenyl H 0 4-chlorophenyl CH 161-154.degree.7.234 F H 0 4-chlorophenyl CH 126-127.degree.7.235 phenyl H 0 CH.sub.2 COOCH.sub.3 CH 127-129.degree.7.236 NO.sub.2 H 0 anilidocarbonyl- CH 162-165.degree. methyl (dec.)7.237 2-Cl,6-CH.sub.3 H 2 p-tolyl CH 150-152.degree. (dec.)__________________________________________________________________________
TABLE 8______________________________________ ##STR45##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.38.002 COOCH.sub.3 0 p-tolyl OCH.sub.38.003 COOCH.sub.3 0 p-tolyl OCHF.sub.28.004 COOCH.sub.3 2 p-tolyl CH.sub.38.005 COOCH.sub.3 2 p-tolyl OCH.sub.38.006 COOCH.sub.3 2 p-tolyl OCHF.sub.28.007 COOCH.sub.3 0 CSN(CH.sub.3).sub.2 CH.sub.38.008 COOCH.sub.3 0 CSN(CH.sub.3).sub.2 OCH.sub.38.009 COOCH.sub.3 0 CSN(CH.sub.3).sub.2 OCHF.sub.28.010 COOCH.sub.3 2 ethyl CH.sub.38.011 COOCH.sub.3 2 ethyl OCH.sub.38.012 COOCH.sub.3 2 ethyl OCHF.sub.28.013 COOCH.sub.3 0 4-chlorophenyl CH.sub.38.014 COOCH 0 4-chlorophenyl OCHF.sub.28.015 COOCH.sub.3 0 4-chlorophenyl OCH.sub.38.016 COOCH.sub.3 2 4-chlorophenyl CH.sub.38.017 COOCH.sub.3 2 4-chlorophenyl OCHF.sub.28.018 COOCH.sub.3 2 4-chlorophenyl OCH.sub.38.019 COOCH.sub.3 0 pyrrolidino thiocarbonyl CH.sub.38.020 COOCH.sub.3 0 pyrrolidino- thiocarbonyl OCH.sub.28.021 COOCH.sub.3 0 pyrrolidino- thiocarbonyl OCHF.sub.28.022 OCHF.sub.2 0 p-tolyl CH.sub.38.023 OCHF.sub.2 0 p-tolyl OCH.sub.38.024 OCHF.sub.2 0 p-tolyl OCHF.sub.28.025 OCHF.sub.2 2 p-tolyl CH.sub.3 154-158.degree. dec.8.026 OCHF.sub.2 2 p-tolyl OCH.sub.38.027 OCHF.sub.2 2 p-tolyl OCHF.sub.28.028 OCHF.sub.2 0 CSN(CH.sub.3).sub.2 CH.sub.38.029 OCHF.sub.2 0 CSN(CH.sub.3).sub.2 OCH.sub.38.030 OCHF.sub.2 0 CSN(CH.sub.3).sub.2 OCHF.sub.28.031 OCHF.sub.2 2 ethyl CH.sub.38.032 OCHF.sub.2 2 ethyl OCH.sub.38.033 OCHF.sub.2 2 ethyl OCHF.sub.28.034 OCHF.sub.2 0 4-chlorophenyl CH.sub.38.035 OCHF.sub.2 0 4-chlorophenyl OCHF.sub.28.036 OCHF.sub.2 0 4-chlorophenyl OCH.sub.38.037 OCHF.sub.2 2 4-chlorophenyl CH.sub.38.038 OCHF.sub.2 2 4-chlorophenyl OCHF.sub.28.039 OCHF.sub.2 2 4-chlorophenyl OCH.sub.38.040 OCHF.sub.2 0 pyrrolidino thiocarbonyl CH.sub.38.041 OCHF.sub.2 0 pyrrolidino- thiocarbonyl OCH.sub.28.042 OCHF.sub.2 0 pyrrolidino- thiocarbonyl OCHF.sub.28.043 Cl 0 p-tolyl CH.sub.38.044 Cl 0 p-tolyl OCH.sub.38.045 Cl 0 p-tolyl OCHF.sub.28.046 Cl 2 p-tolyl CH.sub.38.047 Cl 2 p-tolyl OCH.sub.38.048 Cl 2 p-tolyl OCHF.sub.28.049 Cl 0 CSN(CH.sub.3).sub.2 CH.sub.38.050 Cl 0 CSN(CH.sub.3).sub.2 OCH.sub.38.051 Cl 0 CSN(CH.sub.3).sub.2 OCHF.sub.28.052 Cl 2 ethyl CH.sub.38.053 Cl 2 ethyl OCH.sub.38.054 Cl 2 ethyl OCHF.sub.28.055 Cl 0 4-chlorophenyl CH.sub.38.056 Cl 0 4-chlorophenyl OCHF.sub.28.057 Cl 0 4-chlorophenyl OCH.sub.38.058 Cl 2 4-chlorophenyl CH.sub.38.059 Cl 2 4-chlorophenyl OCHF.sub.28.060 Cl 2 4-chlorophenyl OCH.sub.38.061 Cl 0 pyrrolidino- thiocarbonyl CH.sub.38.062 Cl 0 pyrrolidino- thiocarbonyl OCH.sub.28.063 Cl 0 pyrrolidino- thiocarbonyl OCHF.sub.28.064 NO.sub.2 0 p-tolyl CH.sub.38.065 NO.sub.2 0 p-tolyl OCH.sub.38.066 NO.sub.2 0 p-tolyl OCHF.sub.28.067 NO.sub.2 2 p-tolyl CH.sub.38.068 NO.sub.2 2 p-tolyl OCH.sub.38.069 NO.sub.2 2 p-tolyl OCHF.sub.28.070 NO.sub.2 0 CSN(CH.sub.3).sub.2 CH.sub.38.071 NO.sub.2 0 CSN(CH.sub.3).sub.2 OCH.sub.38.072 NO.sub.2 0 CSN(CH.sub.3).sub.2 OCHF.sub.28.073 NO.sub.2 2 ethyl CH.sub.38.074 NO.sub.2 2 ethyl OCH.sub.38.075 NO.sub.2 2 ethyl OCHF.sub.28.076 NO.sub.2 0 4-chlorophenyl CH.sub.38.077 NO.sub.2 0 4-chlorophenyl OCHF.sub.28.078 NO.sub.2 0 4-chlorophenyl OCH.sub.38.079 NO.sub.2 2 4-chlorophenyl CH.sub.38.080 NO.sub.2 2 4-chlorophenyl OCHF.sub.28.081 NO.sub.2 2 4-chlorophenyl OCH.sub.38.082 NO.sub.2 0 pyrrolidino- thiocarbonyl CH.sub.38.083 NO.sub.2 0 pyrrolidino- thiocarbonyl OCH.sub.28.084 NO.sub.2 0 pyrrolidino- thiocarbonyl OCHF.sub.28.085 COOCH.sub.3 0 CH.sub.3 CH.sub.38.086 COOCH.sub.3 0 CH.sub.3 OCH.sub.38.087 COOCH.sub.3 0 CH.sub.3 OCHF.sub.28.088 COOCH.sub.3 2 CH.sub.3 CH.sub.38.089 COOCH.sub.3 2 CH.sub.3 OCH.sub.38.090 COOCH.sub.3 2 CH.sub.3 OCHF.sub.28.091 OCHF.sub.2 0 CH.sub.3 CH.sub.38.092 OCHF.sub.2 0 CH.sub.3 OCHF.sub.28.093 OCHF.sub.2 0 CH.sub.3 OCH.sub.38.094 OCHF.sub.2 2 CH.sub.3 CH.sub.38.095 OCHF.sub.2 2 CH.sub.3 OCH.sub.38.096 OCHF.sub.2 2 CH.sub.3 OCHF.sub.28.097 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.)______________________________________
TABLE 9__________________________________________________________________________ ##STR46##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 thiocarbonyl9.002 COOCH.sub.3 0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl9.003 COOCH.sub.3 0 pyrrolidino- Cl OCH.sub.3 CH thiocarbonyl9.004 COOCH.sub.3 0 pyrrolidino- N(CH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl9.005 COOCH.sub.3 0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl9.006 COOCH.sub.3 0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl9.007 COOCH.sub.3 0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl9.008 COOCH.sub.3 0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl9.009 COOCH.sub.3 0 dimethylthio- Cl OCH.sub.3 CH carbamoyl9.010 COOCHhd 3 0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 CH carbamoyl9.011 COOCH.sub.3 0 dimethylthio- CH(OCH.sub.3) OCH.sub.3 CH carbamoyl9.012 COOCH.sub.3 0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.013 COOCH.sub.3 0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.014 COOCH.sub.3 0 benzoyl Cl OCH.sub.3 N9.015 COOCH.sub.3 0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 N9.016 COOCH.sub.3 0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.017 COOCH.sub.3 0 benzoyl CH.sub.2 Cl OCH.sub.3 CH9.018 COOCH.sub.3 0 acetyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.019 COOCH.sub.3 0 acetyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.020 COOCH.sub.3 0 acetyl Cl OCH.sub.3 N9.021 COOCH.sub.3 0 acetyl N(CH.sub.3).sub.2 OCH.sub.3 N9.022 COOCH.sub.3 0 acetyl CH(OCH.sub.3).sub.2 OCH.sub. 3 CH9.023 COOCH.sub.3 0 acetyl CH.sub.2 Cl OCH.sub.3 CH9.024 OCHF.sub.2 0 pyrrolidino- CH.sub.2 OCH.sub.3 OCH.sub.3 CH thiocarbonyl9.025 OCHF.sub.2 0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl9.026 OCHF.sub.2 0 pyrrolidino- Cl OCH.sub.3 CH 143-144.degree. thiocarbonyl dec.9.027 OCHF.sub.2 0 pyrrolidino- N(CH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl9.028 OCHF.sub.2 0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl9.029 OCHF.sub.2 0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl9.030 OCHF.sub.2 0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl9.031 OCHF.sub.2 0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl9.032 OCHF.sub.2 0 dimethylthio- Cl OCH.sub.3 N carbamoyl9.033 OCHF.sub.2 0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 N carbamoyl9.034 OCHF.sub.2 0 dimethylthio- CH(OCH.sub.3) OCH.sub.3 CH carbamoyl9.035 OCHF.sub.2 0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.036 OCHF.sub. 2 0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.037 OCHF.sub.2 0 benzoyl Cl OCH.sub.3 N9.038 OCHF.sub.2 0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 CH9.039 OCHF.sub.2 0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.040 OCHF.sub.2 0 benzoyl CH.sub.2 Cl OCH.sub.3 CH9.041 OCHF.sub.2 0 acetyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.042 OCHF.sub.2 0 acetyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.043 OCHF.sub.2 0 acetyl Cl OCH.sub.3 CH9.044 OCHF.sub.2 0 acetyl N(CH.sub.3).sub.2 OCH.sub.3 N9.045 OCHF.sub.2 0 acetyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.046 OCHF.sub.2 0 acetyl CH.sub.2 Cl OCH.sub.3 CH9.047 Cl 0 pyrrolidino- CH.sub.2 OCH.sub.3 OCH.sub.3 CH thiocarbonyl9.048 Cl 0 pyrrolidino- OCH.sub.2 CH.sub.3 CH.sub.3 CH thiocarbonyl9.049 Cl 0 pyrrolidino- Cl OCH.sub.3 CH 141-143.degree. thiocarbonyl dec.9.050 Cl 0 pyrrolidino N(CH.sub.3).sub.2 OCH.sub.3 N thiocarbonyl9.051 Cl 0 pyrrolidino- CH(OCH.sub.3).sub.2 OCH.sub.3 CH thiocarbonyl9.052 Cl 0 pyrrolidino- CH.sub.2 Cl OCH.sub.3 CH thiocarbonyl9.053 Cl 0 dimethylthio- CH.sub.2 OCH.sub.3 OCH.sub.3 CH carbamoyl9.054 Cl 0 dimethylthio- OCH.sub.2 CH.sub.3 CH.sub.3 CH carbamoyl9.055 Cl 0 dimethylthio- Cl OCH.sub.3 CH carbamoyl9.056 Cl 0 dimethylthio- N(CH.sub.3).sub.2 OCH.sub.3 CH carbamoyl9.057 Cl 0 dimethylthio- CH(OCH.sub.3).sub.2 OCH.sub.3 CH carbamoyl9.058 Cl 0 benzoyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.059 Cl 0 benzoyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.060 Cl 0 benzoyl Cl OCH.sub.3 N9.061 Cl 0 benzoyl N(CH.sub.3).sub.2 OCH.sub.3 CH9.062 Cl 0 benzoyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.063 Cl 0 benzoyl CH.sub.2 Cl OCH.sub.3 CH9.064 Cl 0 acetyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.065 Cl 0 acetyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.066 Cl 0 acetyl Cl OCH.sub.3 CH9.067 Cl 0 acetyl N(CH.sub.3).sub.2 OCH.sub.3 N9.068 Cl 0 acetyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.069 Cl 0 acetyl CH.sub.2 Cl OCH.sub.3 CH9.070 COOCH.sub.3 0 2-chlorophenyl CH.sub.2 CH.sub.3 OCH.sub.3 CH9.071 COOCH.sub.3 2 2-chlorophenyl CH.sub.2 CH.sub.3 OCH.sub.3 CH9.072 COOCH.sub.3 0 2-chlorophenyl Cl OCH.sub.3 N9.073 COOCH.sub.3 2 2-chlorophenyl Cl OCH.sub.3 CH9.074 COOCH.sub.3 0 2-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N9.075 COOCH.sub.3 2 2-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 CH9.076 COOCH.sub.3 0 CH.sub.2 CH.sub.3 Cl OCH.sub.3 N9.077 COOCH.sub.3 2 CH.sub.2 CH.sub.3 Cl OCH.sub.3 CH9.078 COOCH.sub.3 0 CH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.079 COOCH.sub.3 2 CH.sub.2 CH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.080 COOCH.sub.3 0 p-tolyl OCH.sub.3 Cl CH9.081 COOCH.sub.3 2 p-tolyl OCH.sub.3 Cl N9.082 COOCH.sub.3 0 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.083 COOCH.sub.3 2 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.084 OCHF.sub.2 0 p-tolyl CH.sub.2 OCH.sub.3 OCH.sub.3 CH9.085 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 CH9.087 COOCH.sub.3 0 methyl OCH.sub.2 CH.sub.3 OCH.sub.3 CH9.088 COOCH.sub.3 0 methyl Cl OCH.sub.3 CH9.089 COOCH.sub.3 0 methyl N(CH.sub.3).sub.2 OCH.sub.3 CH9.090 COOCH.sub.3 0 methyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.091 COOCH.sub.3 0 methyl CH.sub.2 Cl OCH.sub.3 CH9.092 COOCH.sub.3 2 methyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.093 COOCH.sub.3 2 methyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.094 COOCH.sub.3 2 methyl Cl OCH.sub.3 N9.095 COOCH.sub.3 2 methyl N(CH.sub.3).sub.2 OCH.sub.3 N9.096 COOCH.sub.3 2 methyl CH(OCH.sub.3) OCH.sub.3 CH9.097 COOCH.sub.3 0 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.098 COOCH.sub.3 0 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.099 COOCH.sub.3 0 4-chlorophenyl Cl OCH.sub.3 N9.100 COOCH.sub.3 0 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N9.101 COOCH.sub.3 0 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.102 COOCH.sub.3 0 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH9.103 COOCH.sub.3 2 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.104 COOCH.sub.3 2 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.105 COOCH.sub.3 2 4-chlorophenyl Cl OCH.sub.3 N9.106 COOCH.sub.3 2 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N9.107 COOCH.sub.3 2 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.108 COOCH.sub.3 2 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH9.109 OCHF.sub.2 0 methyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.110 OCHF.sub.2 0 methyl OCH.sub.2 CH.sub.3 OCH.sub.3 CH9.111 OCHF.sub.2 0 methyl Cl OCH.sub.3 N9.112 OCHF.sub.2 0 methyl N(CH.sub.3).sub.2 OCH.sub.3 CH9.113 OCHF.sub.2 0 methyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.114 OCHF.sub.2 0 methyl CH.sub.2 Cl OCH.sub.3 CH9.115 OCHF.sub.2 2 methyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.116 OCHF.sub.2 2 methyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.117 OCHF.sub.2 2 methyl Cl OCH.sub.3 N9.118 OCHF.sub.2 2 methyl N(CH.sub.3).sub.2 OCH.sub.3 N9.119 OCHF.sub.2 2 methyl CH(OCH.sub.3) OCH.sub.3 CH9.120 OCHF.sub.2 0 4-chlorophenyl CH.sub.2 OCH.sub. 3 CH.sub.3 CH9.121 OCHF.sub.2 0 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.122 OCHF.sub.2 0 4-chlorophenyl Cl OCH.sub.3 N9.123 OCHF.sub.2 0 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N9.124 OCHF.sub.2 0 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.125 OCHF.sub.2 0 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH9.126 OCHF.sub.2 2 4-chlorophenyl CH.sub.2 OCH.sub.3 CH.sub.3 CH9.127 OCHF.sub.2 2 4-chlorophenyl OCH.sub.2 CH.sub.3 CH.sub.3 CH9.128 OCHF.sub.2 2 4-chlorophenyl Cl OCH.sub.3 N9.129 OCHF.sub.2 2 4-chlorophenyl N(CH.sub.3).sub.2 OCH.sub.3 N9.130 OCHF.sub.2 2 4-chlorophenyl CH(OCH.sub.3).sub.2 OCH.sub.3 CH9.131 OCHF.sub.2 2 4-chlorophenyl CH.sub.2 Cl OCH.sub.3 CH9.132 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 CH9.135 COOC.sub.2 H.sub.5 2 p-tolyl Cl OCH.sub.3 CH9.136 COOCH.sub.3 0 2,4,5-tri- CH.sub.2 OCH.sub.3 OCH.sub.3 CH 128-130.degree. chlorophenyl dec.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. chlorophenyl9.140 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.__________________________________________________________________________
TABLE 10__________________________________________________________________________ ##STR47##__________________________________________________________________________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 CH10.004 COOCH.sub.3 2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH10.005 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 CH10.008 Cl 2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH10.009 OCHF.sub.2 benztriazol-1-yl CH.sub.3 CH.sub.3 CH10.010 OCHF.sub.2 1,2,4-triazol-1-yl CH.sub.3 CH.sub.3 CH10.011 OCHF.sub.2 2-methylbenzimidazol-1-yl CH.sub.3 CH.sub.3 CH10.012 OCHF.sub.2 2,3-dimethylindol-1-yl CH.sub.3 CH.sub.3 CH10.013 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 CH10.015 COOCH.sub.3 1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH10.016 COOCH.sub.3 2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH10.017 COOCH.sub.3 2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH10.018 Cl benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH10.019 Cl 1,2,4-triazol-1-yl OCH.sub.3 OCH.sub.3 CH10.020 Cl 2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH10.021 Cl 2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH10.022 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 CH10.024 OCHF.sub.2 2-methylbenzimidazol-1-yl OCH.sub.3 OCH.sub.3 CH10.025 OCHF.sub.2 2,3-dimethylindol-1-yl OCH.sub.3 OCH.sub.3 CH10.026 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 OCH.sub.3 CH10.027 COOCH.sub.3 benztriazol-1-yl OCH.sub.3 CH.sub.3 CH10.028 COOCH.sub.3 1,2,4-triazol-1-yl OCH.sub.3 CH.sub.3 CH10.029 COOCH.sub.3 2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH10.030 COOCH.sub.3 2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH10.031 Cl benztriazol-1-yl OCH.sub. 3 CH.sub.3 CH10.032 Cl 1,2,4-triazol-1-yl OCH.sub.3 CH.sub.3 CH10.033 Cl 2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH__________________________________________________________________________No R.sup.1 (R.sup.2) R.sup.6 R.sup.3 R.sup.4 E m.p. (.degree.C.)__________________________________________________________________________10.034 Cl 2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH10.035 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 CH10.037 OCHF.sub.2 2-methylbenzimidazol-1-yl OCH.sub.3 CH.sub.3 CH10.038 OCHF.sub.2 2,3-dimethylindol-1-yl OCH.sub.3 CH.sub.3 CH10.039 OCHF.sub.2 benztriazol-1-yl OCH.sub.3 OCHF.sub.2 CH10.040 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)__________________________________________________________________________
Formulation Examples
EXAMPLE 14
Formulation Examples for compounds of formula I (percentages are by weight)
______________________________________(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 emulsionwater 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%______________________________________
Biological Examples
EXAMPLE 15
Preemergence herbicidal action
Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm.sup.3, water-absorbing capacity: 0.565 l/l). After the non-absorptive 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 lightpermeable 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:
______________________________________1 plants have not emerged or are totally withered2-3 very pronounced action4-6 medium action7-8 weak action9 no action (as untreated controls).______________________________________
Preemergence action:
Concentration of the test compound emulsion: 70.8 ppm
______________________________________Test plantCompound Nasturtium Stellaria Agrostis Digitaria______________________________________5.001 2 2 2 25.004 1 1 1 15.007 1 1 1 15.022 2 2 2 25.051 2 2 2 25.061 2 2 2 25.064 1 1 1 15.066 1 1 1 15.089 2 1 1 25.102 2 1 1 25.105 1 1 1 15.107 1 1 1 15.121 2 2 2 25.124 2 2 2 25.130 2 2 2 25.133 2 2 2 25.142 2 2 2 25.165 1 2 1 25.170 2 2 2 25.229 2 2 2 25.230 2 2 2 25.231 2 2 2 25.232 2 1 1 25.235 2 2 2 25.236 2 1 1 25.237 2 2 2 25.238 2 1 2 25.239 2 1 1 15.240 2 2 2 25.241 2 2 2 25.242 2 2 2 25.243 2 3 2 35.244 2 3 2 35.246 3 4 3 55.247 3 5 3 55.252 2 2 2 26.001 2 2 2 26.010 1 1 1 16.011 1 1 1 16.013 2 2 2 26.021 2 2 2 26.040 2 2 2 26.041 2 2 2 26.061 2 1 2 16.230 2 2 3 36.233 3 4 4 56.240 3 3 3 36.242 2 2 2 26.245 1 1 1 16.253 1 1 1 16.254 1 1 1 16.267 2 2 2 26.268 1 1 1 16.269 2 2 2 26.270 2 2 2 27.001 1 1 1 17.061 1 1 1 17.082 2 2 2 27.084 2 2 2 27.141 2 2 2 37.142 2 2 2 27.229 4 5 4 57.230 2 1 1 27.231 2 2 2 37.232 2 2 2 37.234 2 2 2 37.236 2 2 2 27.237 2 1 1 18.004 2 2 2 28.025 2 1 2 18.067 2 2 2 28.097 2 2 2 29.026 1 1 1 29.049 2 2 2 29.083 2 2 2 29.085 2 1 1 29.132 1 1 1 29.133 1 1 1 29.139 2 2 2 29.140 1 1 1 29.141 1 1 1 110.001 2 2 2 210.002 2 2 1 210.005 2 2 4 510.006 2 2 2 210.013 2 3 2 410.022 2 2 1 210.035 2 2 2 210.040 2 2 2 210.041 2 2 2 210.042 2 3 2 310.043 2 2 2 210.044 2 2 2 2______________________________________
EXAMPLE 16
Growth inhibition of tropical cover crops
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 aqueous 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. 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.
EXAMPLE 17
Growth regulation of soybeans
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.
EXAMPLE 18
Growth inhibition of cereals
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 concetration 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.
EXAMPLE 19
Growth inhibition of grasses
Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylis glomerate and Cynodon dactylon 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.
EXAMPLE 20
Root growth
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 height. 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.

Number	Date	Country	Kind
720/84	Feb 1984	CHX
1841/84	Apr 1984	CHX

	Number	Date	Country
Parent	53912	May 1987
Parent	699388	Feb 1985

Herbicidal sulfonylureas

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