Heterocyclic 2-alkoxyphenoxysulfonylureas and the use thereof as herbicides or plant growth regulators

DESCRIPTION
It is known that heterocyclically substituted phenoxysulfonylureas possess herbicidal and plant growth-regulating properties (EP-A 4,163, DE-A 3,151-450).
Surprisingly, it has now been found that heterocyclically substituted sulfamic acid phenyl esters, the phenyl ester moiety of which is formed by selected pyrocatechol monoalkyl ethers, are particularly suitable as herbicides or plant growth regulators.
The present invention therefore relates to compounds of the formula (I) or the salts thereof ##STR3## where
R.sup.1 is ethyl, propyl or isopropyl,
R.sup.2 is halogen, NO.sub.2, CF.sub.3, CN, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio or (C.sub.1 -C.sub.4 -alkoxy)carbonyl,
n is 0, 1, 2 or 3,
Y is O or S,
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of the formulae ##STR4##
E is CH or N,
G is O or CH.sub.2,
R.sup.5 and R.sup.6 independently of one another are hydrogen, halogen, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)alkylthio, it being possible for the abovementioned radicals to be monosubstituted or polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio, furthermore are a radical of the formula --NR.sup.12 R.sup.13, --OCHR.sup.7 --CO.sub.2 R.sup.12, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4 )alkynyl, (C.sub.3 -C.sub.5)alkenyloxy or (C.sub.3 -C.sub.5)alkynyloxy,
R.sup.7 is hydrogen or (C.sub.1 -C.sub.4)alkyl,
R.sup.8 is (C.sub.1 -C.sub.4)alkyl, --CHF.sub.2 or --CH.sub.2 CF.sub.3,
R.sup.9 and R.sup.10 independently of one another are hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.5)alkoxy or halogen,
R.sup.11 is hydrogen, (C.sub.1 -C.sub.4)alkyl, --CHF.sub.2 or CH.sub.2 CF.sub.3 and
R.sup.12 and R.sup.13 independently of one another are hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkynyl.
The compounds of the formula (1) can form salts in which the hydrogen of the --SO.sub.2 --NH-- group is replaced by a cation which is suitable for agriculture. In general, these salts are metal salts, in particular alkali metal salts, alkaline earth metal salts, optionally alkylated ammonium salts or organic amine salts.
In the above definitions, halogen is preferably fluorine, chlorine or bromine.
Preferred compounds of the formula I or salts thereof are those in which n=0 or 1, Y is O, R.sup.2 is orientated in the 6-position of the phenyl ring and has the above-mentioned meaning, in the case of halogen in particular F or Cl, R.sup.3 is hydrogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.3 -C.sub.4)alkenyl, R.sup.4 is a heterocyclic radical of the formula ##STR5## E is CH or N and R.sup.5 and R.sup.6 are halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio, each of which can be substituted as described above.
Particularly preferred compounds of the formula (I) or salts thereof are those where n=0 or 1, R.sup.2 is orientated in the 6-position of the phenyl ring and is fluorine, chlorine, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkoxycarbonyl, R.sup.3 is hydrogen or methyl, R.sup.4 is a heterocyclic radical of the formula ##STR6## E is CH or N and R.sup.5 and R.sup.6 independently of one another are chlorine, bromine, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, OCHF.sub.2 or OCH.sub.2 CF.sub.3 or CF.sub.3, in particular (C.sub.1 -C.sub.2)alkyl or (C.sub.1 -C.sub.2)alkoxy.
The present invention furthermore relates to processes for the preparation of the compounds of the general formula (I) or salts thereof, which comprise reacting
(a) a compound of the formula (II) ##STR7## with a compound of the formula (III) ##STR8## or
(b) a compound of the formula (IV) ##STR9## with a chlorosulfonylurea of the formula (V) ##STR10## or
(c) a compound of the formula (VI) ##STR11## with a carbamate of the formula (VII) ##STR12## where Z is phenyl or (C.sub.1 -C.sub.6)alkyl and, if desired, converting the resulting compounds of the formula I into their salts.
The reaction of the compounds of the formulae (II) and (III) is preferably carried out in inert aprotic solvents, such as, for example, acetonitrile, dichloromethane, toluene, tetrahydrofuran or dioxane, at temperatures between 0.degree. C. and the boiling point of the solvent.
The phenoxysulfonyl isocyanates of the formulae (II) can be prepared in a simple manner by processes which are known in principle from the corresponding pyrocatechol monoethers of the formula (IV) and chlorosulfonyl isocyanate (cf. G. Lohaus, Chem. Ber. 105. 2791 (1972)).
The starting substances of the formula (III) are known or can be prepared by processes which are known in principle, for example by cyclizing corresponding guanidine derivatives with appropriately substituted 1,3-diketones, cf., for example, "The Chemistry of Heterocyclic Compounds", Vol. XVI (1962) and Supplement I (1970), or by derivatization of cyanuric chloride, cf., for example, "The Chemistry of Heterocyclic Compounds", L. Rapaport: "s-Triazines and Derivatives" (1959).
The reaction of the compounds (IV) with the chlorosulfonylureas (V) is preferably carried out in inert solvents, such as, for example, dichloromethane, at temperatures between -10.degree. C. and 80.degree. C. in the presence of a base as the HCl-binding agent. Bases which can be employed are alkali metal carbonates, alkali metal bicarbonates, alkaline earth metal carbonates or alkaline earth metal bicarbonates, such as, for example, K.sub.2 CO.sub.3, NaHCO.sub.3 or Na.sub.2 CO.sub.3, or tertiary amines, such as, for example, pyridine or triethylamine.
The pyrocatechol monoethers (IV) are known from the literature or can be prepared by processes which are known from the literature. The chlorosulfonylureas (V) are accessible from the amines of the formula (III) and chlorosulfonyl isocyanate (EP-A 141,199).
The reaction of the compounds (VI) with the heterocyclic carbamates of the formula (VII) is preferably carried out in the presence of tertiary organic bases, such as, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), in inert solvents, such as acetonitrile or dioxane, at temperatures between 20.degree. C. and the boiling point of the solvent (analogously to EP-A 44,807).
The carbamates (VII) which are required for this are known from the literature or are prepared by known processes (EP-A 70,804). The sulfamates (VI) are prepared from the pyrocatechol monoethers on which they are based by known processes (cf., for example, Synthesis 1978, 357; Z. Chem. 15, 270 (1975); Chem. Ber. 105, 2791 (1972)).
The salts of the compounds of the formula I are preferably prepared in inert solvents, such as, for example, water, methanol or acetone, at temperatures from 0.degree.-100.degree. C. Examples of bases which are suitable for the preparation of the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, ammonia or ethanolamine.
The compounds of the formula I according to the invention have an excellent herbicidal activity against a broad range of economically important monocotyledon and dicotyledon noxious plants. The active substances act equally well on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and which cannot be easily controlled. In this context, it does not matter if the substances are applied before sowing, as a pre-emergence treatment or post-emergence treatment. Some representatives of the monocotyledon and dicotyledon weed flora which can be controlled may be mentioned individually as examples, but this is not to be taken to mean a restriction to certain species.
The monocotyledon weed species controlled include, for example, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria etc. and Cyperus species from the annual group, and the perennial species include Agropyron, Cynodon, Imperata and Sorghum etc., and also perennial Cyperus species. Of the dicotyledon weed species, the range of action covers Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon, Sida etc. from the annual plants, and Convolvulus, Cirsium, Rumex, Artemisia etc. from the perennial weeds.
Excellent control of weeds occurring under the specific culture conditions in rice, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus, Cyperus etc., by the active substances according to the invention is also possible.
If the compounds according to the invention are applied to the soil surface before germination, either emergence of the weed seedlings is prevented completely, or the weeds grow until they have reached the cotyledon stage but growth then comes to a standstill and, after a period of three to four weeks, the plants eventually die completely.
When, in the post-emergence method, the active substances are applied to the green parts of the plants, growth also stops dramatically very soon after the treatment, and the weed plants remain in the growth stage of the time of application, or, after a certain period of time, die more or less rapidly so that competition by the weeds, which is detrimental for the crop plants, can thus be prevented at a very early stage and in a sustained manner by using the novel agents according to the invention.
Even though the compounds according to the invention have an excellent herbicidal activity against monocotyledon and dicotyledon weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, maize, sugar beet, cotton and soya beans, are damaged to a negligible extent only, or not at all. Thus, the present compounds are very suitable for selectively controlling undesired plant growth in agricultural plantations of useful plants.
In addition, the compounds according to the invention have plant growth-regulating properties in crop plants. They have a regulating effect on the plant metabolism and can thus employed for facilitating harvesting, such as, for example, by provoking desiccation, abscission and stunted growth. Furthermore, they are suitable for generally regulating and inhibiting undesired vegetative growth, without simultaneously destroying the plants. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.
The agents according to the invention can be employed in the conventional preparations as wettable powders, emulsifiable concentrates, emulsions, sprayable solutions, dusting agents, seed-dressing agents, dispersions, granules or microgranules.
Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, also contain wetting agents, for example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkylsulfonates or alkylphenylsulfonates, and dispersing agents, for example, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate and also sodium oleoylmethyltaurinate, as well as, if appropriate, a diluent or inert substance. The formulations are prepared in a customary manner, for example by grinding and mixing of the components.
Emulsifiable concentrates can be prepared, for example, by dissolving the active substance in an inert organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene and also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. In the case of liquid active substances, all or part of the solvent component can be omitted. Emulsifiers which can be used are, for example: calcium salts of alkylarylsulfonic acid, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, fatty alcohol/propylene oxide/ethylene oxide condensation products alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
Dusting agents are obtained by grinding the active substance with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite, pyrophillite, or diatomaceous earth.
Granules can be produced either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of excipients such as sand, kaolinites or granulated inert material, by means of binders, for example polyvinyl alcohol, sodium polyacrylate or alternatively mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the preparation of fertilizer granules, if desired in a mixture with fertilizers.
The active substance concentration in wettable powders is, for example, about 10 to 90% by weight; the remainder to 100% by weight comprises conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 5 to 80% by weight. Formulations in the form of dusts usually contain 5 to 20% by weight, sprayable solutions about 2 to 20% by weight. In the case of granules, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries, fillers etc. are used.
In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersing agents, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.
For use, the concentrates, present in commercially available form, are diluted, if appropriate, in a conventional manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and, in some cases, also in the case of microgranules. Preparations in the form of dusts and in the form of granules and also sprayable solutions are usually not further diluted with other inert substances before use.
The application rate required varies with the external conditions, such as temperature, humidity amongst others. It can vary within wide limits between, for example 0.005 and 10.0 kg/ha or more of active substance, preferably, however, it is between 0.01 and 5 kg/ha.
If appropriate, mixtures or mixed formulations with other active substances, such as, for example, insecticides, acaricides, herbicides, fertilizers, growth regulators or fungicides are also possible.
The following examples illustrate the invention in greater detail.
FORMULATION EXAMPLES
A. A dusting agent is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc or inert substance, and comminuting the mixture in a hammer mill.
B. A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substance, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonte and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.
C. A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active substance with 6 parts by weight of alkylphenol polyglycol ether (.RTM.Triton 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to above 377.degree. C.), and grinding the mixture in a ball mill to a fineness of below 5 microns.
D. An emulsifiable concentrate is obtained from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.

CHEMICAL EXAMPLES
EXAMPLE 1
2-Ethoxyphenoxysulfonyl isocyanate
67.9 g (0.48 mol) of chlorosulfonyl isocyanate are added dropwise at 25.degree. C. to a solution of 55.2 g (0.4 mol) of 2-ethoxyphenol in 500 ml of xylene. When the dropwise addition is complete, the temperature is increased slowly to 140.degree. C. and the mixture is refluxed for 2.5 hours. The mixture is cooled, and the solvent as well as excess chlorosulfonyl isocyanate are removed on a rotary evaporator. The yellow oil which remains (97.2 g=100% of theory) is employed without further purification.
EXAMPLE 2
3-(4,6-Dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxysulfonyl)urea
A solution of 97.2 g (0.4 mol) of the product of Example 1 in 100 ml of dichloromethane is added dropwise at 25.degree. C. to 62.0 g (0.4 mol) of 2-amino-4,6-dimethoxypyrimidine in 600 ml of dichloromethane. Stirring at room temperature is continued for 16 hours, the mixture is diluted with 600 ml of dichloromethane, and the organic phase is washed twice with 500 ml portions of 2N hydrochloric acid and once with 500 ml of water. After the mixture has been dried using sodium sulfate and after the solvent has been removed on a rotary evaporator, an oily product remains which crystallizes on trituration with diethyl ether. 145.0 g (91% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxysulfonyl)urea of melting point 145.degree.-147.degree. C. are obtained.
EXAMPLE 3
3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propoxyphenoxysulfonyl)urea
1.74 g (0.008 mol) of 2-propoxyphenyl sulfamate are added at room temperature to 2.32 g (0.0084 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate, dissolved in 100 ml of acetonitrile. After 1.33 g (0.0088 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) have been added, the reaction mixture is stirred at room temperature for 18 hours, concentrated, diluted with H.sub.2 O and acidified using 2N hydrochloric acid to give a pH of 3-4. After the solids have been filtered off with suction and dried, 2.85 g (86% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)- 1-(2-propoxyphenoxysulfonyl)urea of melting point 108.degree.-109.degree. C. are obtained.
The compounds of the Tables which follow are prepared as described in Examples 1-3.
TABLE 1__________________________________________________________________________ ##STR13##Ex. No. R.sup.1 R.sup.2 R.sup.3 R.sup.5 R.sup.6 E n m.p. [.degree.C.]__________________________________________________________________________ 4 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 0 162 5 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 CH 0 125 6 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 N 0 7 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 N 0 128-129 8 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 0 169-170 9 CH.sub.2 CH.sub.3 H OCH.sub.3 SCH.sub.3 N 0 10 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CH 0 134-135 11 CH.sub.2 CH.sub.3 H OCF.sub.2 H CH.sub.3 CH 0 12 CH.sub.2 CH.sub.3 H OCF.sub.2 H OCF.sub.2 H CH 0 140 13 CH.sub.2 CH.sub.3 H OCH.sub.3 Br CH 0 14 CH.sub.2 CH.sub.3 H CH.sub.3 Cl CH 0 163 15 CH.sub.2 CH.sub.3 H OCH.sub.3 H CH 0 16 CH.sub.2 CH.sub.3 H OCH.sub.3 NHCH.sub.3 CH 0 17 CH.sub.2 CH.sub.3 H OCH.sub.3 NHCH.sub.3 N 0 18 CH.sub.2 CH.sub.3 H CH.sub.3 NHCH.sub.3 CH 0 19 CH.sub.2 CH.sub.3 H OC.sub.2 H.sub.5 NHCH.sub.3 N 0 168 20 CH.sub.2 CH.sub.3 H OCH.sub.3 SCH.sub.3 CH 0 21 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.2 H.sub.5 CH 0 22 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.3 H.sub.7 CH 0 23 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.2 H.sub.5 N 0 24 CH.sub.2 CH.sub.3 H Cl OC.sub.2 H.sub.5 CH 0 25 CH.sub.2 CH.sub.3 H OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CH 0 26 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.3 CH 0 27 CH.sub.2 CH.sub.3 H CF.sub.3 OCH.sub.3 CH 0 28 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 CH.sub.3 CH 0 29 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.3 CH 0 30 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3 CH 0 31 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHCH.sub.3 CH 0 32 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.3 N 0 175 33 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHCH.sub.3 N 0 34 CH.sub.2 CH.sub.3 H OCH.sub.3 NHC.sub.2 H.sub.5 CH 0 35 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHC.sub.2 H.sub.5 CH 0 36 CH.sub.2 CH.sub.3 H OCH.sub.3 N(CH.sub.3).sub.2 CH 0 37 CH.sub.2 CH.sub.3 H OCH.sub.3 CH(OCH.sub.3).sub.2 CH 0 38 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 0 113-115 39 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 CH 0 101-102 40 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 N 0 41 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 N 0 93-123 42 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 0 43 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 Cl CH 0 121-123 44 CH.sub.2 CH.sub.2 CH.sub.3 H OCF.sub.2 H CH.sub.3 CH 0 126 45 CH.sub.2 CH.sub.2 CH.sub.3 H OCF.sub.2 H OCF.sub.2 H CH 0 46 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 Br CH 0 47 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 Cl CH 0 48 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 H CH 0 49 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 NHCH.sub.3 CH 0 50 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 NHCH.sub.3 N 0 51 CH.sub.2 CH.sub.2 CH.sub.3 H CH3 NHCH.sub.3 CH 0 52 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 NHCH.sub.3 N 0 53 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 SCH.sub.3 CH 0 54 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.2 H.sub.5 CH 0 127-130 55 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.3 H.sub.7 N 0 56 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OC.sub.2 H.sub.5 N 0 57 CH.sub.2 CH.sub.2 CH.sub.3 H Cl OC.sub.2 H.sub.5 CH 0 58 CH.sub.2 CH.sub.2 CH.sub.3 H OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CH 0 59 CH.sub.2 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.3 CH 0 60 CH.sub.2 CH.sub.2 CH.sub.3 H CF.sub.3 OCH.sub.3 CH 0 61 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 CH.sub.3 CH 0 62 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.3 CH 0 63 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3 CH 0 64 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHCH.sub.3 CH 0 65 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 OCH.sub.3 N 0 66 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHCH.sub.3 N 0 67 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 0 68 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.2 CF.sub.3 NHC.sub.2 H.sub.5 CH 0 69 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 N(CH.sub.3).sub.2 CH 0 70 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH(OCH.sub.3).sub.2 CH 0 71 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 0 90-92 72 CH(CH.sub.3).sub.2 H OCH.sub.3 CH.sub.3 CH 0 135-137 73 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 N 0 74 CH(CH.sub.3).sub.2 H OCH.sub.3 CH.sub.3 N 0 108-110 75 CH(CH.sub.3).sub.2 H OCH.sub.2 OCH.sub.3 CH 0 141-143 76 CH(CH.sub.3).sub.2 H OCH.sub.3 Cl CH 0 121-123 77 CH(CH.sub.3).sub.2 H OCF.sub.2 H CH.sub.3 CH 0 78 CH(CH.sub.3).sub.2 H OCF.sub.2 H OCF.sub.2 H CH 0 135-136 79 CH(CH.sub.3).sub.2 H OCH.sub.3 Br CH 0 80 CH(CH.sub.3).sub.2 H CH.sub.3 Cl CH 0 81 CH(CH.sub.3).sub.2 H OCH.sub.3 H CH 0 82 CH(CH.sub.3).sub.2 H OCH.sub.3 NHCH.sub.3 CH 0 83 CH(CH.sub.3 ).sub.2 H OCH.sub.3 NHCH.sub.3 N 0 84 CH(CH.sub.3).sub.2 H CH.sub.3 NHCH.sub.3 CH 0 85 CH(CH.sub.3).sub.2 H CH.sub.3 NHCH.sub.3 N 0 86 CH(CH.sub.3).sub.2 H OCH.sub.3 SCH.sub.3 CH 0 87 CH(CH.sub.3).sub.2 H OCH.sub.3 OC.sub.2 H.sub.5 CH 0 88 CH(CH.sub.3).sub.2 H OCH.sub.3 OC.sub.3 H.sub.7 CH 0 89 CH(CH.sub.3).sub.2 H OCH.sub.3 OC.sub.2 H.sub.5 N 0 90 CH(CH.sub.3).sub.2 H Cl OC.sub.2 H.sub.5 CH 0 91 CH(CH.sub.3).sub.2 H OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 CH 0 92 CH(CH.sub.3).sub.2 H C.sub.2 H.sub.5 OCH.sub.3 CH 0 93 CH(CH.sub.3).sub.2 H CF.sub.3 OCH.sub.3 CH 0 94 CH(CH.sub.3).sub.2 H OCH.sub.2 CF.sub.3 CH.sub.3 CH 0 95 CH(CH.sub.3).sub.2 H OCH.sub.2 CF.sub.3 OCH.sub.3 CH 0 96 CH(CH.sub.3).sub. 2 H OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3 CH 0 97 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 0 98 CH(CH.sub.3).sub.2 H OCH.sub.2 CF.sub.3 OCH.sub.3 N 0 99 CH(CH.sub.3).sub.2 H OCH.sub.2 CF.sub.3 NHCH.sub.3 N 0100 CH(CH.sub.3).sub.2 H OCH.sub.3 NHC.sub.2 H.sub.5 CH 0101 CH(CH.sub.3).sub.2 H OCH.sub.2 CF.sub.3 NHC.sub.2 H.sub.5 CH 0102 CH(CH.sub.3).sub.2 H OCH.sub.3 N(CH.sub.3).sub.2 CH 0103 CH(CH.sub.3).sub.2 H OCH.sub.3 CH(OCH.sub.3).sub.2 CH 0104 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 OCH.sub.3 CH 1 162-163105 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 CH.sub.3 CH 1 151-152106 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 CH.sub.3 N 1 128-129107 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 Cl CH 1108 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 OCH.sub.3 CH 1109 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 CH.sub.3 CH 1110 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 CH.sub.3 N 1112 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 Cl CH 1113 CH.sub.2 CH.sub.3 6-Br H OCH.sub.3 OCH.sub.3 CH 1114 CH.sub.2 CH.sub.3 5-F H OCH.sub.3 CH.sub.3 CH 1115 CH.sub.2 CH.sub.3 5-Br H OCH.sub.3 CH.sub.3 N 1116 CH.sub.2 CH.sub.3 5-Cl H OCH.sub.3 Cl CH 1117 CH.sub.2 CH.sub.3 5-Cl H OCH.sub.3 OCH.sub.3 CH 1118 CH.sub.2 CH.sub.3 4-Cl H OCH.sub.3 CH.sub.3 CH 1119 CH.sub.2 CH.sub.3 4-F H OCH.sub.3 CH.sub.3 N 1120 CH.sub.2 CH.sub.3 4-Br H OCH.sub.3 Cl CH 1121 CH.sub.2 CH.sub.3 3-Cl H OCH.sub.3 OCH.sub.3 CH 1 148-149122 CH.sub.2 CH.sub.3 3-F H OCH.sub.3 CH.sub.3 CH 1123 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1124 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 Cl CH 1125 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1126 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1127 CH.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1128 CH.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 Cl CH 1129 CH.sub.2 CH.sub.3 4-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1130 CH.sub.2 CH.sub.3 4-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1131 CH.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1132 CH.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 Cl CH 1133 CH.sub.2 CH.sub.3 6-OC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1 194-195134 CH.sub.2 CH.sub.3 6-OC.sub.3 H.sub.7 H OCH.sub.3 CH.sub.3 CH 1135 CH.sub.2 CH.sub.3 6-OC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 N 1136 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub.3 Cl CH 1137 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 163138 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1 148139 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 CH.sub. 3 N 1140 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 Cl CH 1 154-156141 CH.sub.2 CH.sub.3 6-COOC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1 124-125142 CH.sub.2 CH.sub.3 6-COOC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1 128-129143 CH.sub.2 CH.sub.3 5-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1144 CH.sub.2 CH.sub.3 5-COOCH.sub.3 H OCH.sub.3 Cl CH 1145 CH.sub.2 CH.sub.3 4-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1146 CH.sub.2 CH.sub.3 4-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1147 CH.sub.2 CH.sub.3 3-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1148 CH.sub.2 CH.sub.3 3-COOCH.sub.3 H OCH.sub.3 Cl CH 1149 CH.sub.2 CH.sub.3 6-COOC.sub.3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1150 CH.sub.2 CH.sub.3 6-COOC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 CH 1151 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1 139-140152 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 Cl CH 1153 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 177-178154 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1 155-156 (decomp.)155 CH.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1156 CH.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 Cl CH 1 82 (decomp.)157 CH.sub.2 CH.sub.3 4-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1158 CH.sub.2 CH.sub.3 3-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1 118-120159 CH.sub.2 CH.sub.3 6-C.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 N 1 139-141160 CH.sub.2 CH.sub.3 6-C.sub.3 H.sub.7 H OCH.sub.3 Cl CH 1 122-124161 CH.sub.2 CH.sub.3 6-C.sub.4 H.sub.9 H OCH.sub.3 OCH.sub.3 CH 1162 CH.sub.2 CH.sub.3 6-NO.sub.2 H OCH.sub.3 CH.sub.3 CH 1163 CH.sub.2 CH.sub.3 6-CF.sub.3 H OCH.sub.3 CH.sub.3 N 1 155-156164 CH.sub.2 CH.sub.3 6-CN H OCH.sub.3 Cl CH 1165 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1166 CH.sub.2 CH.sub.3 6-SC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1167 CH.sub.2 CH.sub.3 6-SC.sub.5 H.sub.9 H OCH.sub.3 CH.sub.3 N 1168 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub.3 Cl CH 1169 CH.sub.2 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 OCH.sub.3 CH 1170 CH.sub.2 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 CH.sub.3 CH 1171 CH.sub.2 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 CH.sub.3 N 1172 CH.sub.2 CH.sub.2 CH.sub.3 6-Cl H OCH.sub.3 Cl CH 1173 CH.sub.2 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 OCH.sub.3 CH 1174 CH.sub.2 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 OCH.sub.3 CH 1175 CH.sub.2 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 CH.sub.3 N 1176 CH.sub.2 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 Cl CH 1177 CH.sub.2 CH.sub.2 CH.sub.3 6-Br H OCH.sub.3 OCH.sub.3 CH 1178 CH.sub.2 CH.sub.2 CH.sub.3 5-F H OCH.sub.3 CH.sub.3 CH 1179 CH.sub.2 CH.sub.2 CH.sub.3 5-Br H OCH.sub. 3 CH.sub.3 N 1180 CH.sub.2 CH.sub.2 CH.sub.3 5-Cl H OCH.sub.3 Cl CH 1181 CH.sub.2 CH.sub.2 CH.sub.3 5-Cl H OCH.sub.3 OCH.sub.3 CH 1182 CH.sub.2 CH.sub.2 CH.sub.3 4-Cl H OCH.sub.3 CH.sub.3 CH 1183 CH.sub.2 CH.sub.2 CH.sub.3 4-F H OCH.sub.3 CH.sub.3 N 1184 CH.sub.2 CH.sub.2 CH.sub.3 4-Br H OCH.sub.3 Cl CH 1185 CH.sub.2 CH.sub.2 CH.sub.3 3-Cl H OCH.sub.3 OCH.sub.3 CH 1186 CH.sub.2 CH.sub.2 CH.sub.3 3-F H OCH.sub.3 CH.sub.3 CH 1187 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1188 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 Cl CH 1189 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1190 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1191 CH.sub.2 CH.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1192 CH.sub.2 CH.sub.2 CH.sub.3 5-OCH.sub.3 H OCH.sub.3 Cl CH 1193 CH.sub.2 CH.sub.2 CH.sub.3 4-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1194 CH.sub.2 CH.sub.2 CH.sub.3 4-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1195 CH.sub.2 CH.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1196 CH.sub.2 CH.sub.2 CH.sub.3 3-OCH.sub.3 H OCH.sub.3 Cl CH 1197 CH.sub.2 CH.sub.2 CH.sub.3 6-OC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1198 CH.sub.2 CH.sub.2 CH.sub.3 6-OC.sub.3 H.sub.7 H OCH.sub.3 CH.sub.3 CH 1199 CH.sub.2 CH.sub.2 CH.sub.3 6-OC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 N 1200 CH.sub.2 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub.3 Cl CH 1201 CH.sub.2 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1202 CH.sub.2 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1203 CH.sub.2 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1 203a CH.sub.2 CH.sub.2 CH.sub.3 6-COOCH.sub.3 H OCH.sub.3 Cl CH 1204 CH.sub. 2 CH.sub.2 CH.sub.3 6-COOC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1205 CH.sub.2 CH.sub.2 CH.sub.3 6-COOC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1206 CH.sub.2 CH.sub.2 CH.sub.3 5-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1207 CH.sub.2 CH.sub.2 CH.sub.3 5-COOCH.sub.3 H OCH.sub.3 Cl CH 1208 CH.sub.2 CH.sub.2 CH.sub.3 4-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1209 CH.sub.2 CH.sub.2 CH.sub.3 4-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1210 CH.sub.2 CH.sub.2 CH.sub.3 3-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1211 CH.sub.2 CH.sub.2 CH.sub.3 3-COOCH.sub.3 H OCH.sub.3 Cl CH 1212 CH.sub.2 CH.sub.2 CH.sub.3 6-COOC.sub.3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1213 CH.sub.2 CH.sub.2 CH.sub.3 6-COOC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 CH 1214 CH.sub.2 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1215 CH.sub.2 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 Cl CH 1216 CH.sub.2 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1217 CH.sub.2 CH.sub.2 CH.sub.3 6-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1218 CH.sub.2 CH.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1219 CH.sub.2 CH.sub.2 CH.sub.3 5-CH.sub.3 H OCH.sub.3 Cl CH 1220 CH.sub.2 CH.sub.2 CH.sub.3 4-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1221 CH.sub.2 CH.sub.2 CH.sub.3 3-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1222 CH.sub.2 CH.sub.2 CH.sub.3 6-C.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 N 1223 CH.sub.2 CH.sub.2 CH.sub.3 6-C.sub.3 H.sub.7 H OCH.sub.3 Cl CH 1224 CH.sub.2 CH.sub.2 CH.sub.3 6-C.sub.4 H.sub.9 H OCH.sub.3 OCH.sub.3 CH 1225 CH.sub.2 CH.sub.2 CH.sub.3 6-NO.sub.2 H OCH.sub.3 CH.sub.3 CH 1226 CH.sub.2 CH.sub.2 CH.sub.3 6-CF.sub.3 H OCH.sub.3 CH.sub.3 N 1227 CH.sub.2 CH.sub.2 CH.sub.3 6-CN H OCH.sub.3 Cl CH 1228 CH.sub.2 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub. 3 OCH.sub.3 CH 1229 CH.sub.2 CH.sub.2 CH.sub.3 6-SC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1230 CH.sub.2 CH.sub.2 CH.sub.3 6-SC.sub.5 H.sub.9 H OCH.sub.3 CH.sub.3 N 1231 CH.sub.2 CH.sub.2 CH.sub.3 6-SCH.sub.3 H OCH.sub.3 Cl CH 1232 CH(CH.sub.3).sub.2 6-Cl H OCH.sub.3 OCH.sub.3 CH 1233 CH(CH.sub.3).sub.2 6-Cl H OCH.sub.3 CH.sub.3 CH 1234 CH(CH.sub.3).sub.2 6-Cl H OCH.sub.3 CH.sub.3 N 1235 CH(CH.sub.3).sub.2 6-Cl H OCH.sub.3 Cl CH 1236 CH(CH.sub.3).sub.2 6-F H OCH.sub.3 OCH.sub.3 CH 1237 CH(CH.sub.3).sub.2 6-F H OCH.sub.3 CH.sub.3 CH 1238 CH(CH.sub.3).sub.2 6-F H OCH.sub.3 CH.sub.3 N 1239 CH(CH.sub.3).sub.2 6-F H OCH.sub.3 Cl CH 1240 CH(CH.sub.3).sub.2 6-Br H OCH.sub.3 OCH.sub.3 CH 1241 CH(CH.sub.3).sub.2 5-F H OCH.sub.3 CH.sub.3 CH 1242 CH(CH.sub.3).sub.2 5-Br H OCH.sub.3 CH.sub.3 N 1243 CH(CH.sub.3 ).sub.2 5-Cl H OCH.sub.3 Cl CH 1244 CH(CH.sub.3).sub.2 5-Cl H OCH.sub.3 OCH.sub.3 CH 1245 CH(CH.sub.3).sub.2 4-Cl H OCH.sub.3 CH.sub.3 CH 1246 CH(CH.sub.3).sub.2 4-F H OCH.sub.3 CH.sub.3 N 1247 CH(CH.sub.3).sub.2 4-Br H OCH.sub.3 Cl CH 1248 CH(CH.sub.3).sub.2 3-Cl H OCH.sub.3 OCH.sub.3 CH 1249 CH(CH.sub.3).sub.2 3-F H OCH.sub.3 CH.sub.3 CH 1250 CH(CH.sub.3).sub.2 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1251 CH(CH.sub.3).sub.2 6-OCH.sub.3 H OCH.sub.3 Cl CH 1252 CH(CH.sub.3).sub.2 6-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1253 CH(CH.sub.3).sub.2 6-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1254 CH(CH.sub.3).sub.2 5-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1255 CH(CH.sub.3).sub.2 5-OCH.sub.3 H OCH.sub.3 Cl CH 1256 CH(CH.sub.3).sub.2 4-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1257 CH(CH.sub.3).sub.2 4-OCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1258 CH(CH.sub.3).sub. 2 3-OCH.sub.3 H OCH.sub.3 CH.sub.3 N 1259 CH(CH.sub.3).sub.2 3-OCH.sub.3 H OCH.sub.3 Cl CH 1260 CH(CH.sub.3).sub.2 6-OC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1261 CH(CH.sub.3).sub.2 6-OC.sub.3 H.sub.7 H OCH.sub.3 CH.sub.3 CH 1262 CH(CH.sub.3).sub.2 6-OC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 N 1263 CH(CH.sub.3).sub.2 6-SCH.sub.3 H OCH.sub.3 Cl CH 1264 CH(CH.sub.3).sub.2 6-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1265 CH(CH.sub.3).sub.2 6-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1266 CH(CH.sub.3).sub.2 6-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1267 CH(CH.sub.3).sub.2 6-COOCH.sub.3 H OCH.sub.3 Cl CH 1268 CH(CH.sub.3).sub.2 6-COOC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1269 CH(CH.sub.3).sub.2 6-COOC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1270 CH(CH.sub.3).sub.2 5-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1271 CH(CH.sub.3).sub.2 5-COOCH.sub.3 H OCH.sub.3 Cl CH 1272 CH(CH.sub. 3).sub.2 4-COOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1273 CH(CH.sub.3).sub.2 4-COOCH.sub.3 H OCH.sub.3 CH.sub.3 CH 1274 CH(CH.sub.3).sub.2 3-COOCH.sub.3 H OCH.sub.3 CH.sub.3 N 1275 CH(CH.sub.3).sub.2 3-COOCH.sub.3 H OCH.sub.3 Cl CH 1276 CH(CH.sub.3).sub.2 6-COOC.sub.3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1277 CH(CH.sub.3).sub.2 6-COOC.sub.4 H.sub.9 H OCH.sub.3 CH.sub.3 CH 1278 CH(CH.sub.3).sub.2 6-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1279 CH(CH.sub.3).sub.2 6-CH.sub.3 H OCH.sub.3 Cl CH 1280 CH(CH.sub.3).sub.2 6-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1281 CH(CH.sub.3).sub.2 6-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1282 CH(CH.sub.3).sub.2 5-CH.sub.3 H OCH.sub.3 CH.sub.3 N 1283 CH(CH.sub.3).sub.2 5-CH.sub.3 H OCH.sub.3 Cl CH 1284 CH(CH.sub.3).sub.2 4-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1285 CH(CH.sub.3).sub.2 3-CH.sub.3 H OCH.sub.3 CH.sub.3 CH 1286 CH(CH.sub.3).sub.2 6-C.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 N 1287 CH(CH.sub.3).sub.2 6-C.sub.3 H.sub.7 H OCH.sub.3 Cl CH 1288 CH(CH.sub.3).sub.2 6-C.sub.4 H.sub.9 H OCH.sub.3 OCH.sub.3 CH 1289 CH(CH.sub.3).sub.2 6-NO.sub.2 H OCH.sub.3 CH.sub.3 CH 1290 CH(CH.sub.3).sub.2 6-CF.sub.3 H OCH.sub.3 CH.sub.3 N 1291 CH(CH.sub.3).sub.2 6-CN H OCH.sub.3 Cl CH 1292 CH(CH.sub.3).sub.2 6-SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1293 CH(CH.sub.3).sub.2 6-SC.sub.2 H.sub.5 H OCH.sub.3 2 3 CH 1294 CH(CH.sub.3).sub.2 6-SC.sub.5 H.sub.9 H OCH.sub.3 CH.sub.3 N 1295 CH(CH.sub.3).sub.2 6-SCH.sub.3 H OCH.sub.3 Cl CH 1296 CH.sub.2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 Cl CH 2297 CH.sub.2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2298 CH.sub.2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 CH.sub.3 N 2299 CH.sub.2 CH.sub.3 3,5-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2300 CH.sub.2 CH.sub. 2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 Cl CH 2301 CH.sub.2 CH.sub.2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2302 CH.sub.2 CH.sub.2 CH.sub.3 4,6-Cl.sub.2 H OCH.sub.3 CH.sub.3 CH 2303 CH.sub.2 CH.sub.2 CH.sub.3 3,5-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2304 CH(CH.sub.3).sub.2 4,6-Cl.sub.2 H OCH.sub.3 CH.sub.3 N 2305 CH(CH.sub.3).sub.2 4,6-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2306 CH(CH.sub.3).sub.2 4,6-Cl.sub.2 H OCH.sub.3 Cl CH 2307 CH(CH.sub.3).sub.2 3,5-Cl.sub.2 H OCH.sub.3 OCH.sub.3 CH 2308 CH.sub.2 CH.sub.3 4,6-F.sub.2 H OCF.sub.2 H CH.sub.3 CH 2309 CH.sub.2 CH.sub.3 4,6-F.sub.2 H OCH.sub.3 OCH.sub.3 CH 2310 CH.sub.2 CH.sub.3 4,6-F.sub.2 H OCH.sub.3 CH.sub.3 N 2311 CH.sub.2 CH.sub.3 3,5-F.sub.2 H OCH.sub.3 OCH.sub.3 CH 2312 CH.sub.2 CH.sub.2 CH.sub.2 4,6-F.sub.2 H OCH.sub.3 Cl CH 2313 CH.sub.2 CH.sub.2 CH.sub.3 4,6-F.sub.2 H OCH.sub.3 OCH.sub.3 CH 2314 CH.sub.2 CH.sub.2 CH.sub.3 4,6-F.sub.2 H OCF.sub.2 H OCF.sub.2 H CH 2315 CH.sub.2 CH.sub.2 CH.sub.3 3,5-F.sub.2 H OCH.sub.3 OCH.sub.3 CH 2316 CH(CH.sub.3).sub.2 4,6-F.sub.2 H OCH.sub.3 CH.sub.3 N 2317 CH(CH.sub.3).sub.2 4,6-F.sub.2 H OCH.sub.3 OCH.sub.3 CH 2318 CH.sub.2 CH.sub.3 4,6-(CH.sub.3).sub.2 H OCH.sub.3 Cl CH 2319 CH.sub.2 CH.sub.3 4,6-(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 2320 CH.sub.2 CH.sub.3 3,5-(NO.sub.2).sub.2 H OCH.sub.2 CF.sub.3 OCH.sub.3 CH 2321 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CH 0 119-120322 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH.sub.3 N 0 101-102323 CH.sub.2 CH.sub.3 H CH.sub.2 CHCH.sub.2 OCH.sub.3 OCH.sub.3 CH 0324 CH.sub.2 CH.sub.3 H CH.sub.2 CHCH.sub.2 OCH.sub.3 Cl CH 0325 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 OCH.sub.3 CH 0326 CH.sub.2 CH.sub.2 CH.sub. 3 H CH.sub.3 OCH.sub.3 CH.sub.3 CH 0327 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.2 CHCH.sub.2 OCH.sub.3 OCH.sub.3 CH 0328 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.2 CHCH.sub.2 OCH.sub.3 CH.sub.3 N 0329 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 OCH.sub.3 CH 0 127-130330 CH(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 Cl CH 0331 CH(CH.sub.3).sub.2 H CH.sub.2 CHCH.sub.2 OCH.sub.3 OCH.sub.3 CH 0332 CH(CH.sub.3).sub.2 H CH.sub.2 CHCH.sub.2 OCF.sub.2 H CH.sub.3 CH 0333 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 0334 CH.sub.2 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.3 Cl CH 0335 CH(CH.sub.3).sub.2 H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 0336 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.2 CF.sub.3 OCH.sub.3 CH 0337 CH.sub.2 CH.sub.2 CH.sub.3 H C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 0338 CH.sub.2 CH.sub.3 6-CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 N 1339 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1340 CH(CH.sub.3).sub.2 6-Cl CH.sub.2 CHCH.sub.2 OCH.sub.3 Cl CH 1341 CH.sub.2 CH.sub.3 6-F CH.sub.2 CHCH.sub.2 OCH.sub.3 OCH.sub.3 CH 1342 CH.sub.2 CH.sub.2 CH.sub.3 6-CF.sub.3 CH.sub.3 OCH.sub.2 CF.sub.3 OCH.sub.3 N 1343 CH(CH.sub.3).sub.2 6-COOCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1344 CH.sub.2 CH.sub.3 6-C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1 166-167345 " " H OCH.sub.3 CH.sub.3 CH 1 155-156346 " " H OCH.sub.3 Cl CH 1347 " " H CH.sub.3 CH.sub.3 CH 1348 " " H OCH.sub.3 OCH.sub.2 CF.sub.3 N 1349 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1350 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1351 " " H OCF.sub.2 H OCF.sub.2 H CH 1352 " " H OCH.sub.3 OCH.sub.3 N 1353 " 6-C.sub.3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1 158354 " " H OCH.sub.3 CH.sub.3 CH 1 148355 " " H OCH.sub.3 CH.sub.3 N 1 124-126356 " " H OC.sub.2 H.sub.5 NHCH.sub.3 N 1 167-169357 " " H OCH.sub.3 OCH.sub.2 CF.sub.3 N 1 115-117358 " " H CH.sub.3 Cl CH 1 90 (decomp.)359 " 6-OC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 CH 1 157-158360 " " H OCH.sub.3 Cl CH 1 158-159361 CH.sub.2 CH.sub.3 6-OC.sub.2 H.sub.5 H OCH.sub.3 CH.sub.3 N 1 166-167362 " " H CH.sub.3 CH.sub.3 CH 1 139-140363 " " H OCH.sub.3 OCH.sub.2 CF.sub.3 N 1 124364 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1 112-115365 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1366 " " H OCF.sub.2 H OCF.sub.2 H CH 1367 " " H OCH.sub.3 OCH.sub.3 N 1 150-151 (decomp.)368 " 6-CF.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 181369 " " H OCH.sub.3 CH.sub.3 CH 1 151-153370 " " H OCH.sub.3 Cl CH 1371 " " H CH.sub.3 CH.sub.3 CH 1372 " " H OCH.sub.3 OCH.sub.2 CF.sub.3 N 1373 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1374 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1375 " " H OCF.sub.2 H OCF.sub.2 H CH 1376 " " H OCH.sub.3 OCH.sub.3 N 1377 " 6-CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1 88 (decomp.)378 " 5-CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 158-161379 " " H OCH.sub.3 CH.sub.3 CH 1 113 (decomp.)380 " 5-C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1381 " " H OCH.sub.3 CH.sub.3 CH 1382 " 5-Cl H OCH.sub.3 OCH.sub.3 CH 1383 " " H OCH.sub.3 CH.sub.3 CH 1384 " 5-OCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 1385 " " H OCH.sub.3 CH.sub.3 CH 1386 " 6-CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1 102-105 (decomp.)387 " " H OCH.sub.3 OCH.sub.3 N 1 154-155388 CH.sub.2 CH.sub.2 CH.sub.3 6-C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1389 " " H OCH.sub.3 CH.sub.3 CH 1390 " " H OCH.sub.3 Cl CH 1391 " " H CH.sub.3 CH.sub.3 CH 1392 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1393 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1394 " " H OCF.sub.2 H OCF.sub.2 H CH 1395 " 6-C.sub. 3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1 143-145396 " " H OCH.sub.3 CH.sub.3 CH 1397 " " H OCH.sub.3 CH.sub.3 N 1398 " 6-OC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1 138-139399 " " H OCH.sub.3 Cl CH 1400 " " H OCH.sub.3 CH.sub.3 N 1401 " " H CH.sub.3 CH.sub.3 CH 1402 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1 111-113403 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1404 " " H OCF.sub.2 H OCF.sub.2 H CH 1405 " 6-CF.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 165-166406 " " H OCH.sub.3 CH.sub.3 CH 1407 " " H OCH.sub.3 Cl CH 1408 " " H CH.sub.3 CH.sub.3 CH 1409 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1410 " " H OCF.sub.2 H OCF.sub.2 H CH 1 121-122411 " 6-CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1412 " 6-CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1413 CH(CH.sub.3).sub.2 6-C.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1414 " " H OCH.sub.3 CH.sub.3 CH 1415 " " H OCH.sub.3 Cl CH 1416 " " H CH.sub.3 CH.sub.3 CH 1417 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1418 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1419 " " H OCF.sub.2 H OCF.sub.2 H CH 1420 " 6-C.sub.3 H.sub.7 H OCH.sub.3 OCH.sub.3 CH 1 137421 " " H OCH.sub.3 CH.sub.3 CH 1 131-133422 " " H OCH.sub.3 CH.sub.3 N 1423 " 6-OC.sub.2 H.sub.5 H OCH.sub.3 OCH.sub.3 CH 1 129-130424 " " H OCH.sub.3 CH.sub.3 CH 1425 " " H OCH.sub.3 Cl CH 1426 " " H OCH.sub.3 CH.sub.3 N 1427 " " H CH.sub.3 CH.sub.3 CH 1428 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1429 " " CH.sub.3 OCH.sub.3 CH.sub.3 N 1430 " " H OCF.sub.2 H OCF.sub.2 H CH 1431 " 6-CF.sub.3 H OCH.sub.3 OCH.sub.3 CH 1 157-159432 " " H OCH.sub.3 CH.sub.3 CH 1433 " " H OCH.sub.3 Cl CH 1434 " " H CH.sub.3 CH.sub.3 CH 1435 " " CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1436 " " H OCF.sub.2 H OCF.sub.2 H CH 1437 " 6-CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1438 " 6-CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 1439 CH.sub.2 CH.sub.3 3,4,6-F.sub.3 H OCH.sub.3 OCH.sub.3 CH 3440 " 6-Cl C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 1441 " 6-OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 1442 " " C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N 1443 CH.sub.2 CH.sub.2 CH.sub.2 " C.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N 1__________________________________________________________________________
TABLE 2______________________________________ ##STR14##Ex. No. R.sup.1 R.sup.2 R.sup.5 n m.p. [.degree.C.]______________________________________444 CH.sub.2 CH.sub.3 H CH.sub.3 0445 CH.sub.2 CH.sub.3 H H 0446 CH.sub.2 CH.sub.3 H OCH.sub.3 0447 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 0448 CH.sub.2 CH.sub.2 CH.sub.3 H H 0449 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 0450 CH(CH.sub.3).sub.2 H CH.sub.3 0451 CH(CH.sub.3).sub.2 H H 0452 CH(CH.sub.3).sub.2 H OCH.sub.3 0453 CH.sub.2 CH.sub.3 6-CH.sub.3 OCH.sub.3 1454 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 OCH.sub.3 1455 CH(CH.sub.3).sub.2 6-Cl OCH.sub.3 1456 CH.sub.2 CH.sub.3 6-CF.sub.3 OCH.sub.3 1457 CH.sub.2 CH.sub.2 CH.sub.3 6-F OCH.sub.3 1458 CH(CH.sub.3).sub.2 6-OCF.sub.2 H OCH.sub.3 1______________________________________
TABLE 3______________________________________ ##STR15##Ex. No. R.sup.1 R.sup.2 R.sup.5 G n m.p. [.degree.C.]______________________________________459 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.2 0460 CH.sub.2 CH.sub.3 H H CH.sub.2 0461 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.2 0462 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.2 0463 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.2 0464 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.2 0465 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.2 0466 CH(CH.sub.3).sub.2 H H CH.sub.2 0467 CH(CH.sub.3).sub.2 H OCH.sub.3 CH.sub.2 0468 CH.sub.2 CH.sub.3 H CH.sub.3 O 0469 CH.sub.2 CH.sub.3 H H O 0470 CH.sub.2 CH.sub.3 H OCH.sub.3 O 0471 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 O 0472 CH.sub.2 CH.sub.2 CH.sub.3 H H O 0473 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 O 0474 CH(CH.sub.3).sub.2 H CH.sub.3 O 0475 CH(CH.sub.3).sub.2 H H O 0476 CH(CH.sub.3).sub.2 H OCH.sub.3 O 0477 CH.sub.2 CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.2 1478 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 CH.sub.3 O 1479 CH(CH.sub.3).sub.2 6-Cl CH.sub.3 CH.sub.2 1480 CH.sub.2 CH.sub.3 6-CF.sub.3 CH.sub.3 O 1481 CH.sub.2 CH.sub.2 CH.sub.3 6-F CH.sub.3 CH.sub.2 1482 CH(CH.sub.3).sub.2 6-OCF.sub.2 H CH.sub.3 O 1______________________________________
TABLE 4______________________________________ ##STR16##Ex. No. R.sup.1 R.sup.2 R.sup.5 n m.p.______________________________________483 CH.sub.2 CH.sub.3 H CH.sub.3 0484 CH.sub.2 CH.sub.3 H H 0485 CH.sub.2 CH.sub.3 H OCH.sub.3 0486 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 0487 CH.sub.2 CH.sub.2 CH.sub.3 H H 0488 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 0489 CH(CH.sub.3).sub.2 H CH.sub.3 0490 CH(CH.sub.3).sub.2 H H 0491 CH(CH.sub.3).sub.2 H OCH.sub.3 0492 CH.sub.2 CH.sub.3 6-CH.sub.3 OCH.sub.3 1493 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 OCH.sub.3 1494 CH(CH.sub.3).sub.2 6-Cl OCH.sub.3 1495 CH.sub.2 CH.sub.3 6-CF.sub.3 OCH.sub.3 1496 CH.sub.2 CH.sub.2 CH.sub.3 6-F OCH.sub.3 1497 CH(CH.sub.3).sub.2 6-OCF.sub.2 H OCH.sub.3 1______________________________________
TABLE 5______________________________________ ##STR17##Ex. No. R.sup.1 R.sup.2 R.sup.5 R7 n m.p.______________________________________498 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 0499 CH.sub.2 CH.sub.3 H H CH.sub.3 0500 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 0501 CH.sub.2 CH.sub.3 H CH.sub.3 H 0502 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 0503 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 0504 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 0505 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 H 0506 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 0507 CH(CH.sub.3 ).sub.2 H H CH.sub.3 0508 CH(CH.sub.3).sub.2 H OCH.sub.3 CH.sub.3 0509 CH(CH.sub.3).sub.2 H CH.sub.3 H 0510 CH.sub.2 CH.sub.3 6-CH.sub.3 CH.sub.3 H 1511 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 CH.sub.3 CH.sub.3 1512 CH(CH.sub.3).sub.2 6-Cl CH.sub.3 H 1513 CH.sub.2 CH.sub.3 6-CF.sub.3 CH.sub.3 CH.sub.3 1514 CH.sub.2 CH.sub.2 CH.sub.3 6-F CH.sub.3 H 1515 CH(CH.sub.3).sub.2 6-OCF.sub.2 H CH.sub.3 CH.sub.3 1______________________________________
TABLE 6______________________________________ ##STR18##Ex.No. R.sup.1 R.sup.2 R.sup.5 R.sup.6 E n m.p.______________________________________516 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 0517 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 CH 0518 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 N 0519 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 0520 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 CH 0521 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 CH.sub.3 N 0522 CH(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 0523 CH(CH.sub.3).sub. 2 H OCH.sub.3 CH.sub.3 CH 0524 CH(CH.sub.3).sub.2 H OCH.sub.3 CH.sub.3 N 1525 CH.sub.2 CH.sub.3 6-CH.sub.3 OCH.sub.3 CH.sub.3 N 1526 CH.sub.2 CH.sub.2 CH3 6-OCH.sub.3 OCH.sub.3 OCH.sub.3 CH 1527 CH(CH.sub.3).sub.2 6-Cl OCH.sub.3 OCH.sub.3 N 1528 CH.sub.2 CH.sub.3 6-CF.sub.3 OCH.sub.3 CH.sub.3 CH 1529 CH.sub.2 CH.sub.2 CH.sub.3 6-F OCH.sub.3 OCH.sub.3 N 1530 CH(CH.sub.3).sub.2 6-OCF.sub.2 H OCH.sub.3 CH.sub.3 CH 1______________________________________
TABLE 7______________________________________ ##STR19##Ex. No. R.sup.1 R.sup.2 R.sup.8 n m.p.______________________________________531 CH.sub.2 CH.sub.3 H OCH.sub.3 0532 CH.sub.2 CH.sub.3 H CH.sub.3 0533 CH.sub.2 CH.sub.2 CH.sub.3 H OCH.sub.3 0534 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 0535 CH(CH.sub.3).sub.2 H OCH.sub.3 0536 CH(CH.sub.3).sub.2 H CH.sub.3 0537 CH.sub.2 CH.sub.3 6-CH.sub.3 CH.sub.3 1538 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 CH.sub.3 1539 CH(CH.sub.3).sub.2 6-Cl OCH.sub.3 1540 CH.sub.2 CH.sub.3 6-CF.sub.3 CH.sub.3 1541 CH.sub.2 CH.sub.2 CH.sub.3 6-F OCH.sub.3 1542 CH(CH.sub. 3).sub.2 6-OCF.sub.2 H CH.sub.3 1______________________________________
TABLE 8______________________________________ ##STR20##Ex.No. R.sup.1 R.sup.2 R.sup.7 R.sup.8 R.sup.11 n m.p.______________________________________543 CH.sub.2 CH.sub.3 H H OCH.sub.3 H 0544 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 0545 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 0546 CH.sub.2 CH.sub.2 CH.sub.3 H H OCH.sub.3 H 0547 CH.sub.2 CH.sub.2 CH.sub.3 H H CH.sub.3 CH.sub.3 0548 CH.sub.2 CH.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 0549 CH(CH.sub.3).sub.2 H H OCH.sub.3 H 0550 CH(CH.sub.3).sub.2 H H CH.sub.3 CH.sub.3 0551 CH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH.sub.3 0552 CH.sub.2 CH.sub.3 6-CH.sub.3 H CH.sub.3 H 1553 CH.sub.2 CH.sub.2 CH.sub.3 6-OCH.sub.3 H CH.sub.3 CH.sub.3 1554 CH(CH.sub.3).sub.2 6-Cl CH.sub.3 OCH.sub.3 CH.sub.3 1555 CH.sub.2 CH.sub.3 6-CF.sub.3 H CH.sub.3 H 1556 CH.sub.2 CH.sub.3 6-F H OCH.sub.3 CH.sub.3 1557 CH(CH.sub.3).sub.2 6-Cl CH.sub.3 CH.sub.3 CH.sub.3 1______________________________________
BIOLOGICAL EXAMPLES
The damage on the weed plants and the tolerance by crop plants were scored using a key where numbers from 0 to 5 express the activity. In this key
0 denotes no action
1 denotes 0-20% action or damage
2 denotes 20-40% action or damage
3 denotes 40-60% action or damage
4 denotes 60-80% action or damage
5 denotes 80-100% action or damage
1. Pre-emergence action on weeds
Seeds or rhizome pieces of monocotyledon and dicotyledon weed plants were placed in plastic pots containing sandy loam soil and covered with soil. Various dosages of aqueous suspensions or emulsions of the compounds according to the invention formulated as wettable powders or emulsion concentrates were then applied to the surface of the cover soil, at an application rate of water of 600-800 l/ha (converted).
After the treatment, the pots were placed in the greenhouse and maintained at good growth conditions for the weeds. Visual scoring of the damage to plants or of the emergence damage was carried out after the emergence of the test plants after a trial period of 3 to 4 weeks, comparing them to untreated control plants. As shown by the score data in Table 9, the compounds according to the invention have good herbicidal pre-emergence activity against a broad range of weed grasses and broad leaf weeds.
2. Post-emergence action on weeds
Seeds or rhizome pieces of monocotyledon and dicotyledon weeds were placed in plastic pots in sandy loam ground, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated in the three-leaf stage.
Various dosages of the compounds according to the invention formulated as wettable powders or emulsion concentrates were sprayed onto the green parts of the plants, at an application rate of water of 600-800 l/ha (converted), and the action of the preparations was scored visually after the test plants had remained in the greenhouse for about 3 to 4 weeks under optimum growth conditions, comparing them to untreated control plants.
The agents according to the invention exhibit a good herbicidal activity against a broad range of economically important weed grasses and broad-leaf weeds, also in the post-emergence treatment (Table 10).
3. Tolerance by crop plants
In further greenhouse experiments, seeds of a relatively large number of crop plants and weeds were placed in sandy loam ground and covered with soil.
Some of the pots were treated immediately as described under 1., those remaining were placed in the greenhouse until the plants had developed two to three true leaves and were then sprayed with various dosages of the substances according to the invention as described under 2.
Four to five weeks after application, with the plants remaining in the greenhouse, visual scoring revealed that the compounds according to the invention did not cause any damage to dicotyledon crops, such as, for example, soya beans, cotton, oilseed rape, sugar beet and potatoes when applied both as a pre-emergence and post-emergence treatment, even at high dosages of active substance. Furthermore, Gramineae crops such as, for example, barley, wheat, rye, sorghum millet, maize or rice, were also unaffected by some of the substances. Thus, the compounds of the formula I exhibit high selectivity on application for controlling undesired plant growth in agricultural crops.
TABLE 9______________________________________Pre-emergence action of the compounds accordingto the inventionEx. Dosage in No. Herbicidal actionNo. Kg of a.i./ha SIA CRS STM AS ECG LOM______________________________________ 2 0,6 5 5 5 1 3 4 3 0,6 5 5 5 2 3 3 4 0,6 5 5 4 4 4 1 5 0,6 5 4 4 2 2 1 7 0,6 5 5 3 2 2 2 75 0,6 5 5 5 2 2 2104 0,3 5 5 5 1 3 1133 0.3 5 5 5 4 5 5137 0,3 5 5 5 2 4 2138 0,3 5 5 5 5 4 5153 0,3 5 5 5 3 3 4163 0,3 5 5 5 4 4 5321 0,3 5 5 5 1 2 1______________________________________
TABLE 10______________________________________Post-emergence action of the compoundsaccording to the inventionEx. Dosage in No. Herbicidal actionNo. Kg of a.i./ha SIA CRS STM AS ECG LOM______________________________________ 2 0,6 5 5 5 0 4 5 3 0,6 5 5 5 1 4 4 4 0,6 5 4 4 3 4 2 5 0,6 5 5 4 2 2 3 7 0,6 5 5 5 1 3 2 75 0,6 5 5 5 0 5 3104 0,3 5 5 5 3 4 3133 0,3 5 5 5 3 5 5137 0,3 5 4 5 2 4 2138 0,3 5 5 5 4 5 4153 0,3 5 4 5 2 4 2163 0,3 5 5 5 4 4 5321 0,3 4 5 5 1 3 1______________________________________ Abbreviations: SIA = Sinapis alba- CRS = Chrysanthemum segetum- STM = Stellaria media- AS = Avena sativa- ECG = Echinochloa crus-galli- LOM = Lolium multiflorum- a.i. = active substance

Number	Name	Date	Kind
4191553	Reap	Mar 1980
4480101	Meyer	Oct 1984

Number	Date	Country
0004163	Sep 1979	EPX
4163	Sep 1979	EPX
0141199	May 1985	EPX
3151450	Jul 1983	DEX
62-155202	Jul 1987	JPX
2133790	Aug 1984	GBX

Heterocyclic 2-alkoxyphenoxysulfonylureas and the use thereof as herbicides or plant growth regulators

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Entry
AA Gerhard Lohaus, "Darstellung und Umsetzungen von Aryloxysulfonlyisocyanaten", Chem. Ber. 105, pp. 2791 to 2799 (1972).
Chemical Abstracts 108:200229s Kato et al. (1988).
Chemical Abstracts 108: 33622f Kato et al. (1988).