TREA

Phenylacetic acid derivatives and fungicides containing them

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  • Patent Grant
  • 5286750
  • Patent Number
    5,286,750
  • Date Filed
    Monday, March 15, 1993
    32 years ago
  • Date Issued
    Tuesday, February 15, 1994
    31 years ago
Information
Abstract
Unsaturated phenylacetic acid derivatives of the general formula ##STR1## where U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3 or .dbd.CH--S--CH.sub.3 andZ.sup.1 and Z.sup.2 are hydrogen, halogen, trifluoromethyl, cyanide, NO.sub.2 or unsubstituted or substituted alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, COR.sup.4 or NR.sup.5 R.sup.6, and Z.sup.1 and Z.sup.2 may also form a ring,A is meta or para and is (CH.sub.2).sub.n, CH.dbd.CH, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, CH.sub.2 --O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n.n is from 0 to 20,B is substituted or unsubstituted and is hydrogen, alkyl, cycloalkyl, aryl or hetaryl,R.sup.1 to R.sup.7 are hydrogen or unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, hetaryl, aralkyl or cycloalkylalkyl, their acid addition products and base addition products, and fungicides and insecticides containing these compounds.
Description

The present invention relates to phenylacetic acid derivatives having a fungicidal and insecticidal action, fungicides containing these compounds and methods for controlling fungi.
It is known that methyl acrylate derivatives or glyoxylic ester O-methyl oxime derivatives, for example methyl 2-(2-benzoyloxyphenyl)-3-methoxyacrylate (EP-178 826), 2-benzyloxyphenylglyoxylic acid methyl ester O-methyl oxime (DE-36 23 921) or 2-phenyloxymethylenephenylglyoxylic acid methyl ester O-methyl oxime (DE-36 23 921), can be used as fungicides. However, the fungicidal action of these compounds is unsatisfactory.
We have found that novel unsaturated phenylacetic acid derivatives of the formula I ##STR2## where U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3, .dbd.CH--S--CH.sub.3,
Z.sup.1 and Z.sup.2 are identical or different and are each hydrogen, halogen, trifluoromethyl, cyanide, NO.sub.2 or the unsubstituted or substituted radicals alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4 or --NR.sup.5 R.sup.6 or Z.sup.1 and Z.sup.2 together form a ring which is fused with the phenyl radical of which they are substituents,
A is meta or para to the substituted methyl acetate radical and is (CH.sub.2).sub.n, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, CH.dbd.CH--(CH.sub.2).sub.n, CH.sub.2 O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 --O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n, CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n, n is from 0 to 20,
B is hydrogen or the unsubstituted or substituted radicals alkyl, cycloalkyl, aryl or hetaryl, where the radial --A--B must not be hydrogen, and
R.sup.1 to R.sup.7 are identical or different and are each hydrogen or the unsubstituted or substituted radials alkyl, cycloalkyl, alkenyl, alkynyl, aryl, hetaryl, aralkyl or cycloalkylalkyl,
and their plant-tolerated acid addition products or base addition products, except for the compounds of the formulae ##STR3## have high fungitoxic and insecticidal activity and are also very well tolerated by plants.
Acids for acid addition products are, for example, mineral acids, such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or nitric acid, or carboxylic acids, such as formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid, or proton-acidic compounds generally, for example saccharin.
Bases for base addition products are, for example, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and ammonium hydroxide.
In the preparation, the novel compounds of the formula I may be obtained as mixtures of stereoisomers (E/Z isomers, diastereomers, enantismers), which can be separated into the individual components in a conventional manner, for example by crystallization or chromatography. Both the individual isomers and mixtures thereof can be used as fungicides and form subjects of the invention.
Z.sup.1 and Z.sup.2 are each, for example, hydrogen, fluorine, chlorine, bromine, a straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.6 -alkylcarbonyloxy, phenyl, phenoxy, benzyl, benzyloxy, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quinazolyl, quinoxalyl, COOR.sup.1, CONR.sup.2 R.sup.3, COR.sup.4 or NR.sup.5 R.sup.6, or the stated hydrocarbon, aryl or hetaryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfinyl, cyano, hydroxyl and nitro.
Z.sup.1 and Z.sup.2 are each, in particular, hydrogen, fluorine, chlorine, bromine, a straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.6 -alkylcarbonyl, phenyl, phenoxy, benzyl or benzyloxy.
Z.sup.1 and Z.sup.2 are each preferably hydrogen.
A is meta or para to the substituted methyl acetate radical and is (CH.sub.2).sub.n, CH.dbd.CH--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n--CO, CH.sub.2 --O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2) n--CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 --O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n, CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).dbd..sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n.
A is, in particular, (CH.sub.2).sub.n, CH.dbd.CH--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n, CH.sub.2 --O--CO--(CH.sub.2).dbd..sub.n, CH.sub.2 --O--(CH.sub.2).sub.n or CH.sub.2 --S--(CH.sub.2).sub.n.
n is, for example, from 0 to 20, in particular from 0 to 10, preferably 0, 1, 2, 3 or 4.
B is, for example, an unsaturated or saturated straight-chain or branched hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, phenoxy, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quinazolyl or quinoxazolyl, where the stated cycloalkyl, alkyl, aryl or heteraryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfinyl, cyano, hydroxyl and nitro.
B is preferably an unsaturated or saturated straight-chain or branched hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, phenoxy, pyridyl or benzoimidazolyl.
Preferred compounds are those in which the group AB is meta to the group ##STR4##
U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NHCH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.3 --CH.sub.3 or --CH--SCH.sub.3, preferably .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.CH--CH.sub.3 or .dbd.CH--S--CH.sub.3, particularly preferably .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.CH--CH.sub.3.
If U gives rise to syn/anti isomers, the invention relates to all isomers, in particular the anti isomers.
R.sup.1 to R.sup.7 are each, for example, identical or different straight-chain or branched hydrocarbon radicals of 1 to 6, in particular 1 to 4, carbon atoms, cyclic hydrocarbon radicals of 3 to 6 carbon atoms, phenyl, benzyl, cyclohexylmethyl, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzoimidazolyl, quinazolyl or quinoxalyl, where the stated alkyl, cycloalkyl, aryl or hetaryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfinyl, cyano, hydroxyl and nitro.
The novel compounds can be prepared, for example, by the following processes:
The benzyl bromides 2 are obtained by known processes (EP 251 082) from the corresponding phenylacetic esters 1 (Scheme 1). ##STR5##
The ketoesters 5 are key intermediates and can be prepared by reacting the corresponding haloaromatics 3 with magnesium and then reacting the resulting Grignard compounds 4 with dimethyl oxalate (M. Rambaud et al., Synthesis 1988, 564), oxalic acid imidazolide methyl ester (EP 253 213) or oxalyl chloride methyl ester. The derivatives 6 can be synthesized (Scheme 2) from the ketoesters 5 by reaction with CH.sub.3 ON.sup.+ H.sub.3 Cl.sup.- or by a Wittig reaction with (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --O--CH.sub.3 X.sup.- or (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.3 X.sup.-, where X is halogen. ##STR6##
X: Halogen
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.CH--OCH.sub.3
Alternatively, the ketoesters 5 are obtainable from the corresponding aldehydes 7 (Scheme 3).
The aldehydes 7 are converted into the corresponding cyanohydrins 8 by reaction with HCN. The cyanohydrins 8 are converted by reaction with HCl and methanol into the imidoester hydrochlorides 9, which are then hydrolyzed to the mandelic esters 10. These mandelic esters 10 can then be oxidized with NaOCl/tetramethylpiperidin-N-oxyl (Tempo; P. Anelli et al., JOC 52 (1987), 2559) to the ketoesters 5 (Scheme 3). ##STR7##
Either the ketoesters 5 can be brominated with NBS (N-bromosuccinimide) to give the ketoester bromides 11 (Scheme 4) or their keto functions can be reacted with P.sup.+ (C.sub.6 H.sub.5).sub.3 --CH.sub.2 --O--CH.sub.3.sup.- Cl (EP 178 826), CH.sub.3 --O--NH.sub.3 .sup.- Cl (EP 253 213) or H.sub.2 N--NHCH.sub.3 (OZ 39 772). The subsequent NBS bromination of these derivatives 12 then gives the benzyl bromides 13 (Scheme 4). ##STR8##
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
NBS: N-bromosuccinimide
The benzyl bromides 14 can be reacted with nucleophiles, eg. carboxylates (OZ 39 491), phenolates, alcoholates (EP 251 082), mercaptans (EP 226 917), amines, etc. by standard processes to give the novel compounds 15 (Scheme 5). ##STR9##
U: .dbd.O, .dbd.CH--OCH .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3
A: CH.sub.2 --O--(CH.sub.2 O).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n, CH.sub.2 --O--CO(CH.sub.2).sub.n or CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n
n, B, Z.sup.1, Z.sup.2 or R.sup.7 : as defined above
Furthermore, the benzyl bromides 14 can be reacted with phosphites or phosphines to give phosphonates 16 or phosphonium salts 17, which then react with aldehydes to give the styrene derivatives 18. Hydrogenation of these styrene derivatives 18 with a diimine or with H.sub.2 in the presence of a suitable hydrogenation catalyst, eg. Pd or Pt, in a suitable organic solvent, such as tetrahydrofuran, methanol or acetic acid, gives the alkylated aromatics 19 (cf. EP 229 974; Scheme 6). ##STR10##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
B, R.sup.8, R.sup.9 and n: as defined above
The benzyl bromides 14 can also be oxidized with oxidizing agents, such as N-methylmorpholine N-oxide (OZ 50/40842, DE 2948058) or dimethyl sulfoxide (Nace et al., J. Org. Chem. 24 (1959), 1782) to give the aldehydes 20. ##STR11##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
These aldehydes 20 react, for example in Wittig reactions similar to Scheme 6, with phosphonates or phosphonium salts to give the styrene derivatives 18.
The aldehydes 20 can also be reacted with, for example, amines or hydroxyamines or HCN to give Schiff's bases or oxime ethers 21 (Scheme 8) or cyanohydrins 22 (Scheme 9). ##STR12##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
A: CH.dbd.N--O--(CH.sub.2).sub.n or CH.dbd.N--(CH.sub.2).sub.n,
B, Z.sup.1, Z.sup.2 or n: as defined above
The hydroxyl function of the cyanohydrins 22 can be further reacted. Thus, acylated cyanohydrins 23 are obtained, for example, by reacting the compounds 22 with acyl chlorides (Scheme 9). ##STR13##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
B, n, Z.sup.1 or Z.sup.2 : as defined above
The benzyl bromides 11 can likewise (cf. Scheme 5) be reacted with nucleophiles, such as carboxylates, alcoholates, mercaptans, etc., the derivatives 24 being obtained. The compounds 24 can be converted into the active ingredients 25 by means of a Wittig reaction with (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --O--CH.sub.3 Cl.sup.- (EP 178 826), C.sub.6 H.sub.5 P.sup.+ --CH.sub.3 X.sup.- (X=halogen), (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.3 X.sup.- (X=halogen; DE 3705389) or (C.sub.3 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.2 --CH.sub.3 X.sup.- (X=halogen) or by reaction with CH.sub.3 --O--N.sup.+ H.sub.3 Cl.sup.- (EP 253 213) or H.sub.2 N--NHCH.sub.3 (Scheme 10) . ##STR14##
A: CH.sub.2 --O--CO, CH.sub.2 --O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n or CH.sub.2 --NR.sup.7 (CH.sub.2).sub.n
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
B, n, Z.sup.1, Z.sup.2 or R as defined above.
Active ingredients of the structure 28 are obtained from the corresponding hydroxyphenylacetic esters 26, for example by alkylation of the compounds 26 to give the phenyl ethers 27 and subsequent formulation/methylation of 27 (EP 251 082) to give the active ingredients 28 (Scheme 11). ##STR15##
A: O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n+1 --CO or O--(CH.sub.2).sub.n+2 --O
B, n, Z.sup.1 or Z.sup.2 : as defined above
Alternatively, the hydroxyl function of the compounds 26 can be protected by a suitable protective group, eg. tetrahydropyranyl or benzyl.
Formylation/methylation (EP 251 082) of these protected phenols 29 then gives the methyl .alpha.-phenyl-.beta.-methoxyacrylates 30, from which the phenols 31 can be liberated by treatment with hydrochloric acid in methanol or by catalytic hydrogenation (Scheme 12). ##STR16##
SG: Protective group, eg. benzyl or tetrahydropyranyl
The phenols 31 can then be reacted with electrophiles under standard conditions, the active ingredients 32 being obtained (Scheme 13). ##STR17##
A: O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O or O--(CH.sub.2).sub.n+2 --O
B, n, Z.sup.1 or Z.sup.2 : as defined above
Other useful starting materials for the preparation of the novel compounds 41 are the hydroxybenzaldehydes 33.
The hydroxybenzaldehydes 33 can be reacted with benzyl bromide under base catalysis. The benzylated derivatives 34 thus obtained are converted into the corresponding cyanohydrins 35 by reaction with HCN.
These can be reacted with methanol and hydrochloric acid to give the imidoester hydrochlorides 36, which can be hydrolyzed to the mandelic esters 37.
The compounds 37 are oxidized with tetramethylpiperidine-N-oxyl (Tempo: P. Anelli et al., JOC 52 (1987), 2559)/NaOCl to give the ketoesters 38. These can be subjected to hydrogenolysis to give the phenols 39, which in turn react with methoxyamine hydrochloride or H.sub.2 N--NHCH.sub.3 to give the phenolic building blocks 40. These can be etherified or esterified, the novel active ingredients 41 being obtained (Scheme 14). Alternatively, the ketoesters 39 are etherified or esterified to the compounds 42. The derivatives 42 are then converted into the active ingredients 41 by reaction with CH.sub.3 --O--NH.sub.3 Cl or H.sub.2 N--NHCH.sub.3 (Scheme 14). ##STR18##
A: O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O or O--(CH.sub.2).sub.n+2 --O
U: .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
B, n, Z.sup.1 or Z.sup.2 : as defined above
The ketoesters 38 can on the other hand also be subjected to Wittig reactions under base catalysis with (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --O--CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.3 X.sup.- or (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.2 --CH.sub.3 X.sup.- to give the benzyl ethers 43 (X=halogen).
The benzyl group can then be eliminated from these by hydrogenolysis or a free radical reaction, the phenols 44 being obtained. These can be etherified or esterified to the active ingredients 45 in reactions similar to Schemes 13 and 14 (Scheme 15). ##STR19##
U: .dbd.CH--OCH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
A: O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O or O--(CH.sub.2).sub.n+2 --O
B, n, Z.sup.1 and Z.sup.2 : as defined above
Alternatively, the active ingredients 48 can be prepared by a method similar to Schemes 14 and 15 by introducing the side chain into the hydroxybenzaldehydes 33 themselves.
The benzaldehydes 46 thus obtained are then converted by the method described in Scheme 14 into the phenylketoacetates 47, which give the active ingredients 48 by a Wittig reaction with (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --O--CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.3 X.sup.- or (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.2 --CH.sub.3 X.sup.+ (X=halogen) or by reaction with CH.sub.3 --O--N.sup.+ H.sub.3 Cl.sup.- or H.sub.2 N--NHCH.sub.3 (Scheme 16). ##STR20##
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
A: O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O or O--(CH.sub.2).sub.n+2 --O
B, n, Z.sup.1 and Z.sup.2 : as defined above
The benzyl bromides 11 described in Scheme 4 can also be used for the synthesis of further key intermediates (Scheme 17). For example, the benzyl bromides 11 can be reacted with Na acetate or K acetate in highly solvating solvents, such as dimethylformamide or N-methylpyrrolidone, to give the acetates 49. The latter react under base catalysis with (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --O--CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.3 X.sup.-, (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.3 X.sup.- or (C.sub.6 H.sub.5).sub.3 P.sup.+ --CH.sub.2 --CH.sub.2 --CH.sub.3 X.sup.- (X=halogen) in Wittig reactions or with CH.sub.3 ON.sup.+ H.sub.3 Cl.sup.- or H.sub.2 N--NHCH.sub.3, the derivatives 50 being formed.
The benzyl alcohols 51 and 52 are obtainable from the derivatives 49 and 50 by alkaline ester hydrolyis with aqueous alkali in the presence of a solubilizer, such as acetonitrile, dioxane or tetrahydrofuran. ##STR21##
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
The benzyl bromides 13, likewise obtained according to Scheme 4, can be converted into the acetates 53 (Scheme 18) similarly to Scheme 17. ##STR22##
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3 or .dbd.N--NH--CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
The benzyl alcohols 54 can be converted into the benzaldehydes 55 by oxidation with suitable oxidation agents, such as dimethyl sulfoxide or pyridinium chlorochromate, into the benzoic acid 56 by oxidation with, for example, chromium(VI) oxide in acetone/sulfuric acid and into the bromides 57 or chlorides 58 by reaction with suitable hydrogenating agents, eg. PBr.sub.3 or HBr or PCl.sub.5, SOCl.sub.2 or PCl.sub.3 (Scheme 19). ##STR23##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
The active ingredients 59 are obtainable (Scheme 19) from the benzaldehydes 55 similarly to the reactions described in Schemes 6, 8 and 9. ##STR24##
A: HC.dbd.CH, CH.sub.2 --CH.sub.2, CH(CN)--OH, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
B, Z.sup.1 and Z.sup.2 : as defined above
The benzoic acids 56 can be esterified under standard conditions, the benzoic esters 60 being obtained (Scheme 21). ##STR25##
U: .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3 or .dbd.CH--CH.sub.2 --CH.sub.3
Z.sup.1 and Z.sup.2 : as defined above
The benzyl bromides 57 or chlorides 58 can be converted into stilbene or dihydrostilbenes 61 in reactions similar to Scheme 6, via their phosphonium salts or phosphonates (Scheme 22). ##STR26##
U: .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, --CH--CH.sub.3 or --CH--CH.sub.2 --CH.sub.3
A: HC.dbd.CH, H.sub.2 C--CH.sub.2
B, Z.sup.1 and Z.sup.2 : as defined above
The thioenolethers 63 can be prepared from the corresponding oxo analogs 64 by methods known from the literature (EP 178 826) (Scheme 23). ##STR27##
A, B, Z.sup.1 and Z.sup.2 : as defined above
The Examples which follow illustrate the preparation of the novel compounds.





EXAMPLE 1
a) Methyl m-methylmandelate
A mixture of 65 g (1 mol) of KCN and 53.5 g (1 mol) of NH.sub.4 Cl in 300 ml of water and 60 g (0.5 mol) of m-tolylaldehyde in 500 Ml Of ether is stirred overnight at room temperature (20.degree. C.). Thereafter, the organic phase is separated off, extracted twice with water, dried and evaporated down.
67.6 g of the cyanohydrin are obtained as a reddish brown oil.
67.6 g (about 0.5 mol) of the crude cyanohydrin product are dissolved in 600 ml of ether and the solution is cooled to 0.degree. C.
32 g (1 mol) of methanol and 136 ml (0.6 mol) of a 4.4 M solution of hydrochloric acid in ether are added in succession and the mixture is stirred overnight at 10.degree.-15.degree. C. and for a further two days at room temperature. The imidoester hydrochloride which is crystallized out is filtered off under suction, washed with ether, transferred to a flask and hydrolyzed by boiling for 30 minutes with water.
The aqueous phase is cooled to room temperature and extracted twice with ether. The ether phase is filtered over a short silica gel column, dried over MgSO.sub.4 and evaporated down. 40 g (0.22 mol; 44% based on m-tolylaldehyde) of methyl m-methylmandelate are obtained as the residue in the form of a yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 2.3 (s, 3H); 3.7 (s, 3H); 4.1 (s, broad, 1H); 5.1 (s, 1H); 7.1 (m, 4H).
b) Methyl m-methylphenylglyoxylate (Table 1, Number 1, abbreviation: 1/1)
170 ml of 12.5% strength NaOCl solution are added dropwise at 20.degree. C. to a stirred mixture of 40 g (0.22 mol) of methyl m-methylmandelate and 1.5 g (9.6 mmol) of tetramethylpiperidine-N-oxyl in 200 ml of CH.sub.2 Cl.sub.2 and 1.4 g (13 mmol) KBr, 3.5 g (25 mmol) of NaH.sub.2 PO.sub.4.H.sub.2 O and 4.3 g (25 mmol) of Na.sub.2 HPO.sub.4.2 H.sub.2 O in 200 ml of water.
Stirring is carried out for 3 hours at room temperature, after which the organic phase is separated off, washed with NAHCO.sub.3 solution and water and evaporated down.
The residue obtained comprises 37.5 g (0.21 mol, 96%) of methyl m-methylphenylglyoxylate as a yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 2.4 (s, 3H); 4.0 (s, 3H); 7.4 (m, 2H); 7.8 (m, 2H).
EXAMPLE 2
a) Methyl m-bromomethylenephenylglyoxylate (Table 1, Number 2, abbreviation 1/2)
18 g (0.1 mol) of methyl m-methylphenylglyoxylate, 20 g (0.11 mol) of N-bromosuccinimide and 0.1 g (0.6 mmol) of azoisobutyronitrile in 200 ml of CCl.sub.4 are exposed for 4 hours to a 300 watt UV lamp, the solution heating up to the reflux temperature.
The precipitated succinimide is then filtered off under suction. The organic phase is washed with water, dried with MgSO.sub.4 and filtered under suction over a little silica gel, and the filtrate is evaporated down. 28.6 g of a reddish brown oil are obtained, which is shown by NMR analysis to contain 65% of the desired compound methyl m-bromomethylenephenylglyoxylate (70%, based on methyl m-methylphenylglyoxylate), about 20% of the corresponding dibromide and about 15% of starting material.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 4.0 (s, 3H); 4.55 (s, 2H); 7.3-8.2 (m, 4H).
b) Methyl m- (o-methylphenoxymethylene) -phenylglyoxylate (Table 2, Number 490, abbreviation 2/490)
0.6 g (24 mmol) of NaH is added a little at a time to a solution of 2.2 g (20.4 mmol) of o-cresol in 50 ml of dimethylformamide at room temperature, vigorous evolution of gas occurring. 5.1 g of the crude methyl m-bromomethylenephenylglyoxylate (Example 1c; contains 13 mmol of the benzyl bromide) are then added. The reaction mixture warms up to about 40.degree. C.
Stirring is carried out for 4 hours at room temperature, the reaction mixture is diluted with water and the aqueous phase is extracted several times with ether. The combined ether phases are washed several times with Na.sub.2 CO.sub.3 solution and water, dried over MgSO.sub.4 and evaporated down.
The residue is purified by column chromatography, after which 3.8 g of the desired product, contaminated with o-cresol, are obtained.
Bulb tube distillation (0. 1 mbar; 175.degree.-225.degree. C.) gives 2.4 g (65%) of methyl m-(o-methylphenoxymethylene)phenylglyoxylate as a yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 4.0 (s, 3H); 5.1 (s, 2H); 6.7-7.2 (m, 4H); 7.5 (t, J=9Hz, 1H); 7.7 (d, J=9Hz, 1H); 8.0 (d, J=9Hz, 1H); 8.1 (d, J=9Hz, 1H).
EXAMPLE 3
Methyl 2-[m-(o-methylphenoxymethylene)-phenyl]-crotonate (Table 6, Number 65, abbreviation 6/65)
5.8 ml of a 15% strength solution of butyllithium in hexane are added to 4.2 g (10 mmol) of ethyltriphenylphosphonium iodide in 20 ml of tetrahydrofuran at 0.degree. C. while stirring.
After 30 minutes at room temperature, the mixture is cooled to -780.degree. C., a pale yellow solid being precipitated, and a solution of 2.4 g (8 mmol) of methyl m-(o-methylphenoxymethylene)-phenylglyoxylate in tetrahydrofuran is added. The color of the reaction mixture changes from orange to yellow.
The reaction mixture is stirred for 2 hours at room temperature, after which it is poured onto water, the phases are separated and the aqueous phase is extracted several times with ether.
The ether phase is dried over MgSO.sub.4 and filtered under suction over a short silica gel column, and the filtrate is evaporated down.
The remaining oil is chromatographed once with 5:1 cyclohexane/ethyl acetate and once with 4:1 cyclohexane/methylene chloride. 0.8 g (34%) of methyl 2-[m-(o-methylphenoxymethylene)-phenyl]-crotonate is obtained as a yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 1.7 (d, 8Hz, 3H); 2.3 (s, 3H); 3.7 (s, 3H); 5.1 (s, 2H); 6.8-7.5 (m, 9H).
EXAMPLE 4
m-Methylphenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 37, abbreviation 1/37)
15 g (84 mmol) of methyl m-methylphenylglyoxylate and 8.3 g (100 mmol) of O-methylhydroxylamine hydrochloride in 150 ml of methanol are refluxed for 5 hours. Thereafter, the solvent is evaporated off and the residue is filtered with ether over silica gel.
Evaporating off the ether gives 16.2 g (93%) of m-methylphenylglyoxylic acid methyl ester O-methyl oxime as an oily cis/trans mixture (nonpolar isomer:polar isomer=25:1).
.sup.1 H-NMR (CDCl.sub.3): .delta. (nonpolar isomer): 2.35 (s, 3H); 3.93 (s, 3H); 4.0 (s, 3H); 7.1-7.5 (m, 4H); .delta. (polar isomer) 2.38 (s, 3H) ; 3.87 (s, 3H) ; 4.05 (s, 3H); 7.1-7.5 (m, 4H).
EXAMPLE 5
m-Bromomethylenephenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 38, abbreviation 1/38)
15 g (72.4 mmol) of m-methylphenylglyoxylic acid methyl ester O-methyl oxime, 13.5 g (75.8 mmol) of N-bromosuccinimide and 0.1 g (0.6 mmol) of azobisisobutyrodinitrile in 150 ml of CH.sub.2 Cl.sub.2 are exposed for 4 hours to a 300 watt UV lamp, the reaction mixture being refluxed. Thereafter, the organic phase is extracted with water, dried over MgSO.sub.4 and evaporated down.
Purification by column chromatography gives 10.7 g of the nonpolar isomer and 6.1 g of the polar isomer, each of which contains about 5% of the corresponding dibromide and about 10% of the starting material.
.sup.1 H-NMR (CDCl.sub.3): .delta. (nonpolar isomer): 3.95 (s, 3H); 4.05 (s, 3H); 4.5 (s, 2H); 7.2-7.5 (m, 3H); 7.6 (s, 1H); .delta. (polar isomer): 3.90 (s, 3H); 4.10 (s, 3H); 4.5 (s, 2H); 7.2-7.5 (m, 4H).
EXAMPLE 6
m-(6-methyl-2-oxymethylenepyridyl)-phenylglyoxylic acid methyl ester O-methyl oxime (Table 20, Number 2, abbreviation 20/2)
0.18 g (6.3 mmol) of NaH is added to 0.76 g (7 mmol) of 2-hydroxy-6-methylpyridine in 20 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, after which evolution of gas has ceased.
2 g of m-bromomethylenephenylglyoxylic acid methyl ester O-methyl oxime (nonpolar isomer, containing 1.7 g (6 mmol) of the substituted benzyl bromide) are then added and the mixture is stirred overnight at room temperature. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether. The combined ether phases are extracted with water, dried over MgSO.sub.4 and evaporated down.
The oily residue is chromatographed with 1:1 cyclohexane/methylene chloride.
0.5 g (27%) of m-(6-methyl-2-oxymethylenepyridyl)-phenylglyoxylic acid methyl ester O-methyl oxime is obtained as a yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 2.45 (s, 3H); 3.95 (s, 3H); 4.05 (s, 3H); 5.4 (s, 2H); 6.6 (d, J=8Hz, 1H); 6.75 (d, J=8Hz, 1H); 7.3-7.6 (m, 4H); 7.7 (s, 1H).
EXAMPLE 7
2-(N-methyl-N-phenyl-m-aminomethylphenyl)-3-methoxyacrylate (Table 2, Number 88)
2.9 g (10 mmol) of methyl 2-(m-bromomethylphenyl)-3-methoxyacrylate (prepared similarly to EP 226 917) and 1.1 g (10 mmol) of N-methylaniline in 30 ml of CH.sub.2 Cl.sub.2 are stirred for 1 hour at room temperature and for 5 hours while refluxing. Thereafter, the organic phase is extracted with NaHCO.sub.3 solution and water, dried over MgSO.sub.4 and evaporated down.
Chromatography with 10:1 cyclohexane/ethyl acetate gives 2.5 g (80%) of the title compound as a pale yellow oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.0 (s, 3H); 3.65 (s, 3H); 3.75 (s, 3H); 4.5 (s, 3H); 6.6-6.8 (m, 3H); 7.0-7.4 (m, 6H); 7.5 (s, 1H).
EXAMPLE 8
a) Methyl 2-(m-formylphenyl)-3-methoxyacrylate (Table 1, Number 22)
5.7 g (20 mmol) of methyl 2-(m-bromomethylphenyl)-3-methoxyacrylate and 6.7 g (50 mmol) of N-methylmorpholine N-oxide monohydrate in 100 ml of CCl.sub.4 are refluxed for 7 hours. The reaction mixture is cooled and is extracted once with water, once with 2 N HCl and again with water. The organic phase is dried over MgSO.sub.4 and evaporated down.
The oily residue is chromatographed with 4:1 cyclohexane/ethyl acetate, after which 3.0 g (13.6 mmol, 68%) of methyl 2-(m-formylphenyl)-3-methoxyacrylate are obtained as a colorless oil.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.75 (s, 3H); 3.85 (s, 3H); 7.5 (t, J=8Hz, 1H); 7.65 (m, 2H); 7.8 (d, broad, J=8Hz, 1H); 7.9 (s, broad, 1H); 10 (s, 1H).
b) Methyl 2-[m-(.alpha.-phenylcarboxy)-cyanomethylphenyl]-3-methoxyacrylate ((Table 2, Number 95)
A mixture of 2.9 g (13 mmol) of methyl 2-(m-formylphenyl)-3-methoxyacrylate in 20 ml of ether and 1.7 g (26 mmol) of KCN and 1.5 g (26 mmol) of NH.sub.4 Cl in 7.5 ml of water is stirred at room temperature overnight, after which only a small amount of starting material is detectable by thin layer chromatography.
Thereafter, the reaction mixture is diluted with a little water, and the aqueous phase is separated off and is extracted twice with ether. The combined organic phases are dried over MgSO.sub.4 and evaporated down.
The remaining oil is subjected to coarse chromatographic purification to give 2.4 g of a colorless oil, which is directly reacted further.
1.4 g (10 mmol) of benzoyl chloride are added dropwise to 2.4 g (about 10 mmol) of the crude cyanohydrin product, 1.1 g (11 mmol) of triethylamine and 0.1 g of p-N-dimethylaminopyridine in 20 ml of CH.sub.2 Cl.sub.2 while cooling slightly, a white solid being precipitated.
After 1 hour at room temperature, the reaction mixture is washed once with water, twice with Na bisulfite solution and again with water, dried over MgSO.sub.4 and evaporated down. The remaining oil is chromatographed once with 8:1 cyclohexane/ethyl acetate and once with 0.1% methanol in methylene chloride, after which 2.1 g (6 mmol), 46% based on methyl 2-(m-formylphenyl)-3-methoxyacrylate) of the title compound are obtained as a colorless oil.
.sup.1 H-NMR (CDCl.sub.2): .delta.: 3.75 (s, 3H); 3.85 (s, 3H); 6.7 (s, 1H), 7.4-7.7 (m, 9H); 8.1 (d, J=8Hz, 1H).
EXAMPLE 9
2-(p-Benzyloxyphenyl)-3-methoxyacrylate (Table 1, Number 33)
90 g (0.54 mol) of methyl 4-hydroxyphenylacetate, 60 g (0.71 mol) of dihydropyran and 0.1 g of p-toluenesulfonic acid are combined. The temperature of the mixture initially decreases to 5.degree.-10.degree. C. but increases again in the course of the reaction and is kept at 30.degree.-35.degree. C. by cooling in a water bath. After 1 hour, the excess dihydropyran is stripped off under reduced pressure from a water pump.
The crude tetrahydropyranyl ether product is dissolved in 220 ml of methyl formate, and 44 g (0.78 mol) of NaOCH.sub.3 are added while cooling to about 10.degree. C.
After 2 hours at room temperature, the reaction mixture is diluted with CH.sub.2 Cl.sub.2 and water and the aqueous phase is acidified to pH 4.5 with dilute hydrochloric acid and is extracted several times with CH.sub.2 Cl.sub.2. The combined organic phases are dried over MgSO.sub.4 and evaporated down.
The oily crude product obtained as the residue is dissolved in 700 ml of . . . , 90 g (0.65 mol) of K.sub.2 CO.sub.3 and 74 g (0.59 mol) of dimethyl sulfate are added and the mixture is stirred overnight at room temperature.
The reaction mixture is then evaporated down in a rotary evaporator and the residue is diluted with water. The aqueous phase is extracted several times with ether. The combined ether phases are dried over MgSO.sub.4 and evaporated down.
The crude methyl 2-(p-tetrahydropyranyloxyphenyl)-3-methoxyacrylate thus obtained is dissolved in 700 ml of methanol, and 0.5 ml of concentrated hydrochloric acid and 5 ml of water are added. After 2 hours at room temperature, 2 g of NaHCO.sub.3 are added and the reaction mixture is evaporated down in a rotary evaporator.
The oily residue is taken up in CH.sub.2 Cl.sub.2, and the solution is dried over MgSO.sub.4 and evaporated down. The residue is partially crystalline and is stirred with methyl tert-butyl ether. The solid is filtered off under suction, the mother liquor is evaporated down and the residue is chromatographed.
The title compound is obtained as a white solid (mp.=107.degree.-109.degree. C.) in a total yield of 66 g (0.32 mol; 59%, based on methyl p-hydroxyphenyl acetate).
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.75 (s, 3H); 3.8 (s, 3H); 6.75 (d, J=8Hz, 2H); 7.15 (d, J=8Hz, 2H); 7.5 (s, 1H).
EXAMPLE 10
2-(p-Benzyloxyphenyl)-3-methoxyacrylate (Table 3, Number 14)
1. 8 g (10. 5 mmol) of benzyl bromide are added, at -20.degree. C., to 2.1 g (10 mmol) of methyl 2-(p-hydroxyphenyl)-3-methoxyacrylate and 0.56 g (10 mmol) of KOH powder in 20 ml of dimethylformamide. Stirring is then carried out for 3 hours at room temperature. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether.
The combined ether phases are extracted with water, dried over MgSO.sub.4 and evaporated down. Chromatographic purification of the oily residue gives 2.4 g (8.1 mmol, 80%) of the title compound as a colorless solid (mp.=77.degree.-79.degree. C.).
.sup.1 H-NMR (CDCl.sub.3) : .delta.: 3.75 (s, 3H); 3.85 (s, 3H); 5.1 (s, 2H); 6.95 (d, J=11Hz, 2H); 7.2-7.5 (m, 7H); 7.55 (s, 1H).
EXAMPLE 11
Methyl 2-m-(phenylcarbonylmethyleneoxyphenyl)-3-methoxyacrylate (Table 2, Number 19)
0.3 g (12 mmol) of sodium hydride is added a little at a time to 2.1 g (10 mmol) of methyl 2-m-hydroxyphenyl-3-methoxyacrylate (Table 1, Number 24; prepared similarly to Example 5a) in 20 ml of dimethylformamide.
After the end of the addition, the reaction mixture is stirred for 30 minutes at room temperature, after which 3.3 g (1.6 mmol) of a-bromoacetophenone are added.
Stirring is continued overnight at room temperature, after which the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether. The ether phase is extracted with water, dried over magnesium sulfate and evaporated down.
The remaining oil is chromatographed, 1.1 g (3.4 mmol, 34%) of the title compound being obtained as a white solid (mp. 103.degree.-105.degree. C.).
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.35 (s, 2H); 3.65 (s, 3H); 3.8 (s, 3H); 5.55 (s, 2H); 6.8 (m, 3H); 7.2 (t, J=8Hz, 1H); 7.5-7.8 (m, 4H); 8.05 (d, J=8Hz, 2H).
EXAMPLE 12
a) Methyl m-benzyloxymandelate
61 g (0.5 mol) of m-hydroxybenzaldehyde, 86 g (0.5 mol) of benzyl bromide and 70 g (0.5 mol) of K.sub.2 CO.sub.3 in 500 ml of ethanol are refluxed for 3 hours.
The solid is then filtered off and the ethanol is evaporated off in a rotary evaporator. Thereafter, the residue is taken up in CH.sub.2 Cl.sub.2 and the organic phase is extracted with 1 NAOH and twice with water. The solution is dried over MgSO.sub.4 and the solvent is evaporated under reduced pressure.
The residue obtained comprises 102.5 g of m-benzyloxybenzaldehyde as a reddish brown oil.
A mixture of 102.5 g of the above crude benzyl ether in 400 ml of ether and 65 g (1 mol) of KCN and 53.5 g (1 mol) of NH.sub.4 Cl in 300 ml of water is stirred overnight at room temperature. Thereafter, the organic phase is separated off, extracted twice with NaCl solution, dried over MgSO.sub.4 and evaporated down. The residue obtained comprises 113 g of m-benzyloxymandelonitrile as a brown oil which is directly reacted further.
140 ml of 4.4 molar hydrochloric acid solution (0.62 mol) in ether are added, at 0.degree.-50.degree. C., to 113 g of the crude mandelonitrile product and 32 g (1 mol) of methanol in 500 ml of ether. Stirring is carried out overnight at 5.degree.-15.degree. C.; the corresponding imidoester hydrochloride is precipitated and is filtered off under suction and washed with ether (yield: 107 g). The solid is transferred to a round-bottomed flask and boiled for 30 minutes with 500 ml of water. Thereafter, the reaction mixture is cooled to room temperature and the aqueous phase is extracted with ether.
The combined ether phases are filtered with suction through silica gel, dried over MgSO.sub.4 and evaporated down.
86 g (0.32 mol; 63%, based on m-hydroxybenzaldehyde) of methyl m-benzyloxymandelate are obtained as a residue.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.5 (s, broad, 1H); 3.7 (s, 3H); 5.05 (s, 2H); 5.15 (s, 1H); 6.8-7.1 (m, 3H); 7.2-7.5 (m, 6H).
b) Methyl m-benzyloxyphenylglyoxylate
245 ml of 12.5% strength NaOCl solution are added dropwise to a stirred mixture of 86 g (0.32 mol) of methyl m-benzyloxymandelate and 2 g (13 mmol) of tetramethylpiperidine-1-oxyl in 250 ml of CH.sub.2 Cl.sub.2 and 1.95 g (16 mmol) of KBr, 4.9 g (28 mmol) of Na.sub.2 HPO.sub.4.2H.sub.2 O and 6.1 g (44 mmol) of NaH.sub.2 PO.sub.4.H.sub.2 O in 250 ml of water, while cooling with a water bath.
Stirring is carried out for 3 hours at room temperature, the aqueous phase is separated off and the organic phase is extracted with NaHCO.sub.3 solution and with water. The organic phase is dried over MgSO.sub.4 and evaporated down. 78 g (0.29 mol, 90%) of methyl m-benzyloxyphenylglyoxylate are obtained as a residue.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.95 (s, 3H); 5.1 (s, 2H); 7.1-7.7 (m, 9H).
EXAMPLE 13
m-Benzyloxyphenylglyoxylic acid methyl ester O-methyl oxime (Table 2, Number 119)
4 g (15 mmol) of methyl m-benzyloxyphenylglyoxylate and 1.4 g (17 mmol) of O-methylhydroxylamine hydrochloride in 25 ml of ethanol are refluxed for 3 hours. The reaction mixture is then evaporated down. The residue is taken up in ether and the insoluble constituents are filtered off.
The solvent is evaporated off and the remaining residue is purified by column chromatography.
3.1 g (10.4 mmol, 69%) of the nonpolar isomer (colorless crystals, mp.=62.degree.-63.degree. C.) and 0.9 g (3 mmol, 20%) of the polar isomers (colorless crystals, mp.=63.degree.-64.degree. C.) of the title compound are obtained.
.sup.1 H-NMR (CDCl.sub.3) of the nonpolar isomer: .delta.: 3.9 (s, 3H); 4.0 (s, 3H); 5.05 (s, 2H); 6.95-7.5 (m, 9H).
.sup.1 H-NMR (CDCl.sub.3) of the polar isomer: .delta.: 3.85 (s, 3H); 4.05 (s, 3H); 5.05 (s, 2H); 7.0 (m, 3H); 7.2-7.5 (m, 6H).
EXAMPLE 14
a) m-Hydroxyphenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 42)
65 g (0.24 mol) of methyl m-benzyloxyglyoxylate and 6 g of 10% strength Pd/C in 500 ml of methanol are stirred at 60.degree. C. under hydrogen (1 bar).
After a reaction time of 8 hours in each case, the hydrogenation catalyst is filtered off and the same amount of fresh catalyst is added.
After a total reaction time of 32 hours, the reaction is complete. The catalyst is filtered off and the reaction mixture is evaporated down. The residue obtained comprises 42 g of methyl m-hydroxyphenylglyoxylate as an oily crude product.
21 g of the above crude product and 10 g (0.12 mol) of O-methylhydroxylamine hydrochloride in 200 ml of methanol are refluxed for 2 hours.
Thereafter, the solvent is distilled off, the residue is taken up in ether and the undissolved constituents are filtered off. The ether is evaporated off and the residue thus obtained is purified by column chromatography. 8.7 g (42 mmol; 35%, based on methyl mbenzyloxyphenylglyoxylate) of the nonpolar isomer (pale yellow oil) and 4.2 g (20 mmol; 17%, based on methyl mbenzyloxyphenylglyoxylate) of the polar isomer of the title compound are obtained.
.sup.1 H-NMR (CDCl.sub.3) of the nonpolar isomer: .delta.: 3.9 (s, 3H); 4.0 (s, 3H); 5.7 (s, broad, 1H); 6.9 (d, J=8Hz, 1H); 7.1 (m, 2H); 7.2 (t, J=8Hz, 1H).
.sup.1 H-NMR (CDCl.sub.3) of the polar isomer: .delta.: 3.85 (s, 3H); 4.05 (s, 3H); 6.2 (s, broad, 1H); 6.8-7.0 (m, 3H); 7.2 (t, J=8Hz, 1H).
EXAMPLE 15
m-(o-Fluorobenzyloxy)-phenylglyoxylic acid methyl ester O-methyl oxime (Table 5, Number 1)
0.3 g (12.5 mmol) of sodium hydride is added a little at a time to 2.1 g (10 mmol) of m-hydroxyphenylglyoxylic acid methyl ester O-methyl oxime (nonpolar isomer:polar isomer=2:1) in 20 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, 1.9 g (10 mmol) of 2-fluorobenzyl bromide are added and stirring is continued overnight at room temperature.
The reaction mixture is then diluted with water and extracted with ether. The combined ether phases are extracted with water, dried over MgSO.sub.4 and evaporated down. Purification of the residue by column chromatography gives 1.7 g (5.4 mmol, 54%) of the nonpolar isomer (pale yellow oil) and 0.5 g (1.6 mmol, 16%) of the polar isomer (colorless solid, mp.=77.degree.-79.degree. C.) of the title compound.
.sup.1 H-NMR (CDCl.sub.3) of the nonpolar isomer: .delta.: 3.9 (s, 3H); 5.1 (s, 2H); 6.9-7.6 (m, 8H).
.sup.1 H-NMR (CDCl.sub.3) of the polar isomer: .delta.: 3.85 (s, 3H), 4.05 (s, 3H); 5.1 (s, 2H); 6.9-7.6 (m, 8H).
EXAMPLE 16
Methyl 2-(p-acetoxyphenyl)-3-methoxyacrylate (Table 3, Number 22)
3 g (10.5 mmol) of methyl 2-(p-bromomethylphenyl)-3-methoxyacrylate (prepared similarly to EP 226 917), 1.1 g (11.2 mmol) of potassium acetate and 50 mg of potassium iodide in 70 ml of N-methylpyrrolidone are stirred for 3 hours at 70.degree.-80.degree. C. The reaction mixture is diluted with water and extracted three times with ether. The combined ether phases are washed with water, dried over MgSO.sub.4 and evaporated down. Purification of the residue by column chromatography gives 2.3 g (8.7 mmol, 83%) of the title compound as colorless crystals (mp.= 69.degree.-70.degree. C.).
.sup.1 H-NMR (CDCl.sub.3): .delta.: 2.1 (s, 3H); 3.75 (s, 3H); 3.85 (s, 3H); 5.1 (s, 2H); 7.35 (s, 4H); 7.6 (s, 1H).
EXAMPLE 17
Methyl 2- (p-hydroxymethylphenyl) -3-methoxyacrylate (Table 1, Number 36)
12 g (45 mmol) of methyl 2-(p-acetoxyphenyl)-3-methoxyacrylate in 200 ml of dioxane and 1.9 g (47 mmol) of NAOH in 100 ml of water are stirred for 24 hours at room temperature. A further 1.8 g of NAOH are added, stirring is carried out for 30 minutes and the reaction mixture is evaporated down under reduced pressure.
The residue is taken up with dilute hydrochloric acid and the aqueous phase is extracted three times with ether. The ether phase is filtered under suction over Al.sub.2 O.sub.3 and the solvent is evaporated off. The residue obtained comprises 4.2 g (19 mmol, 40%) of the title compound as a colorless oil.
.sup.1 H-NMR (CDCl.sub.3 ): .delta.: 2.4 (s, broad, 1H); 3.75 (s, 3H); 3.85 (s, 3H); 4.65 (s, 2H); 7.3 (s,-4H); 7.55 (s, 1H)
EXAMPLE 18
Methyl 2-(p-carboxyphenyl)-3-methoxyacrylate (Table 1, Number 32)
5 ml of Jones reagent (L. Chinn, Selection of Oxidants in Synthesis, Marcel Dekker, New York 1971, page 42) are added dropwise, at from -10.degree. to -20.degree. C., to 2.2 g (10 mmol) of methyl 2-(p-hydroxymethylphenyl)-3-methoxyacrylate in 20 ml of acetone. The mixture is allowed to reach room temperature and a further 3 ml of Jones reagent are added to the greenish solution, after which a permanent orange color is obtained.
The excess oxidizing agent is decomposed by adding a little methanol, the precipitated greenish solid is filtered off under suction and the solvent is evaporated under reduced pressure. The residue is taken up in CH.sub.2 Cl.sub.2 and the organic phase is extracted twice with water, dried over MgSO.sub.4 and evaporated down.
The residue is purified by column chromatography, after which 0.8 g (3.4 mmol, 34%) of the title compound is obtained.
.sup.1 H-NMR (CDCl.sub.3): .delta.: 3.75 (s, 3H) ; 3. 9 (s, 3H) ; 7.45 (d, J=8Hz, 2H) ; 7.6 (s, 1H); 8.1 (d, J=8Hz, 2H); 11.4 (s, broad, 1H).
EXAMPLE 19
Methyl 2-(p-carboxymethylphenyl)-3-methoxyacrylate (Table 3, Number 26)
0.3 g (12.5 mmol) of sodium hydride is added a little at a time to 1 g (4 mmol) of methyl 2-(p-carboxyphenyl)-3-methoxyacrylate in 10 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, after which 1.3 g (10 mmol) of dimethyl sulfate are added. Stirring is continued for a further 30 minutes, the mixture is diluted with 100 ml of 1% strength NH.sub.4 OH solution and the aqueous phase is extracted with methylene chloride. The solvent is evaporated off, the residue is taken up in ether and the ether-insoluble residue is filtered off under suction and discarded.
The organic phase is washed with water, dried over MgSO.sub.4 and evaporated down.
Purification of the residue by column chromatography gives 0.5 g (2 mmol, 50%) of the title compound as colorless crystals (mp.=81.degree.-84.degree. C.).
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.75 (s, 3H); 3.9 (s, 3H); 3.95 (s, 3H); 7.45 (d, J=8Hz, 2H); 7.6 (s, 1H); 8.05 (d, J=8Hz, 2H).
TABLE 1__________________________________________________________________________ ##STR28##No. U Y mp NMR: .delta. (ppm)__________________________________________________________________________ 1 O 3-CH.sub.3 oil 2.4(S, 3H,); 4.0(S, 3H) 2 O 3-CH.sub.2 Br oil 4.0(S, 3H); 4.5(S, 2H) 3 O 3-CH.sub.2 Cl 4 O 3-CHO 5 O 3-COOH 6 O 3-PO(OCH.sub.3).sub.2 7 O 3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.- 8 O 3-CH.sub.2 OH 9 O 4-CH.sub.2 Br10 O 4-CH.sub.2 Cl11 O 4-CHO12 O 4-COOH13 O 4-PO(OCH.sub.3).sub.214 O 4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-15 O 4-CH.sub.2 OH16 HCOCH.sub.3 3-CH.sub.3 58-6117 HCOCH.sub.3 3-CH.sub.2 Br 90-9118 HCOCH.sub.3 3-CH.sub.2 Cl19 HCOCH.sub.3 3-CHO oil 7.6(S, 1H); 10.0(S, 1H)20 HCOCH.sub.3 3-COOH 158-16221 HCOCH.sub.3 3-OH 94-9622 HCOCH.sub.3 3-PO(OCH.sub.3).sub.2 93- 9423 HCOCH.sub.3 3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-24 HCOCH.sub.3 3-CH.sub.2 OH oil 4.6(S, 1H); 7.55(S, 1H)25 HCOCH.sub.3 4-CH.sub.3 62-6326 HCOCH.sub.3 4-CH.sub.2 Br 76-8127 HCOCH.sub.3 4-CH.sub.2 Cl28 HCOCH.sub.3 4-CHO29 HCOCH.sub.3 4-COOH 158-16230 HCOCH.sub.3 4-OH 107-10931 HCOCH.sub.3 4-PO(OCH.sub.3).sub.232 HCOCH.sub.3 4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-33 HCOCH.sub.3 4-CH.sub.2 OH 62-63 34a) NOCH.sub.3 3-CH.sub.3 oil 2.35(S, 3H); 3.9(S, 3H);non-polar isomer 4.0(S, 3H) 34b) NOCH.sub.3 3-CH.sub.3 66-67polar isomer 35a) NOCH.sub.3 3-CH.sub.2 Br 74-75non-polar isomer 35b) NOCH.sub.3 3-CH.sub.2 Br 68-6936 NOCH.sub.3 3-CH.sub.2 Cl37 NOCH.sub.3 3-CHO38 NOCH.sub.3 3-COOH39 NOCH.sub.3 3-PO(OCH.sub.3).sub.240 NOCH.sub.3 3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-41 NOCH.sub.3 3-CH.sub.2 .sup.- OH42 NOCH.sub.3 4-CH.sub.343 NOCH.sub.3 4-CH.sub.2 Br44 NOCH.sub.3 4-CH.sub.2 Cl45 NOCH.sub.3 4-CHO46 NOCH.sub.3 4-COOH47 NOCH.sub.3 4-PO(OCH.sub.3).sub.248 NOCH.sub.3 4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-49 NOCH.sub.3 4-CH.sub.2 OH50 CHCH.sub.3 3-CH.sub.351 CHCH.sub.3 3-CH.sub.2 Br52 CHCH.sub.3 3-CH.sub.2 Cl53 CHCH.sub.3 3-CHO54 CHCH.sub.3 3-COOH55 CHCH.sub.3 3-OH56 CHCH.sub.3 3-PO(OCH.sub.3).sub.257 CHCH.sub.3 3-P.sup.+ (C.sub.6 H.sub.5).sub.3 .sup.- Cl58 CHCH.sub.3 3-CH.sub.2 OH59 CHCH.sub.3 4-CH.sub.360 CHCH.sub.3 4-CH.sub.2 Br61 CHCH.sub.3 4-CH.sub.2 Cl62 CHCH.sub.3 4-CHO63 CHCH.sub.3 4-COOH64 CHCH.sub.3 4-OH65 CHCH.sub.3 4-PO(OCH.sub.3).sub.266 CHCH.sub.3 4-P.sup.+ (C.sub.6 H.sub.5).sub.3 .sup.- Cl67 CHCH.sub.3 4-CH.sub.2 OH__________________________________________________________________________
TABLE 2 ##STR29## No. U A B mp NMR: .delta. (ppm) 1 HCOCH.sub.3 CH.sub.2 CH.sub.2 H 2 HCOCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 3 HCOCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 4 HCOCH.sub.3 CH.sub.2 CH.sub.2 phenyl oil 2.95(S, 4H); 7.55(S, 1H) 5 HCOCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 6 HCOCH.sub.3 CHCH H 7 HCOCH.sub.3 CHCH CH.sub.3 8 HCOCH.sub.3 CHCH cyclohexyl 9 HCOCH.sub.3 CHCH 2-naphthyl 10 HCOCH.sub.3 CHCH 2-pyridyl 11 HCOCH.sub.3 OCH.sub.2 H oil 3.7; 3, 78; 3.82(3S, 9H); 7.55(S, 1H) 12 HCOCH.sub.3 OCH.sub.2 CH.sub.3 43-45 13 HCOCH.sub.3 OCH.sub.2 cyclohexyl 14 HCOCH.sub.3 OCH.sub.2 phenyl oil 5.05(S, 2H); 7.55(S, 1H) 15 HCOCH.sub.3 O CH.sub.2 2-pyridyl 16 HCOCH.sub.3 OCH.sub.2 CO H 17 HCOCH.sub.3 OCH.sub.2 CO CH.sub.3 18 HCOCH.sub.3 OCH.sub.2 CO cyclohexyl 19 HCOCH.sub.3 OCH.sub.2 CO phenyl 103-105 20 HCOCH.sub.3 OCH.sub.2 CO 2-pyridyl 21 HCOCH.sub.3 CH.sub.2 OCO H oil 5.2(S, 2H); 7.55(S, 1H) 22 HCOCH.sub.3 CH.sub.2 OCO CH.sub.3 34-35 23 HCOCH.sub.3 CH.sub.2 OCO cyclohexyl 24 HCOCH.sub.3 CH.sub.2 OCO phenyl oil 5.4(S, 2H); 7.6(S, 1H) 25 HCOCH.sub.3 CH.sub.2 OCO 2-pyridyl 26 HCOCH.sub.3 COOCH.sub.2 H 27 HCOCH.sub.3 COOCH.sub.2 CH.sub.3 28 HCOCH.sub.3 COOCH.sub.2 cyclohexyl 29 HCOCH.sub.3 COOCH.sub.2 phenyl 30 HCOCH.sub.3 COOCH.sub.2 2-pyridyl 31 HCOCH.sub.3 OCOCH.sub.2 H 32 HCOCH.sub.3 OCOCH.sub.2 CH.sub.3 33 HCOCH.sub.3 OCOCH.sub.2 cyclohexyl 34 HCOCH.sub.3 OCOCH.sub. 2 phenyl 65-66 35 HCOCH.sub.3 OCOCH.sub.2 2-pyridyl 36 HCOCH.sub.3 OCO phenyl 98-99 37 HCOCH.sub.3 OCH.sub.2 COO CH.sub.3 51-53 38 HCOCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 oil 4.0(t, J=7Hz, 3H); 7.55(S, 1H) 39 HCOCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3 oil 3.95(t, J=7Hz, 2H); 7.55(S, 1H) 40 HCOCH.sub.3 O(CH.sub.2).sub.2 O H oil 4.1(t, J=5Hz, 2H), 7.55(S, 1H) 41 HCOCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3 42 HCOCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl 43 HCOCH.sub.3 ( OCH.sub.2).sub.2 O phenyl oil 4.3(S, 4H); 7.55(S, 1H) 44 HCOCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl 45 HCOCH.sub.3 O(CH.sub.2).sub.3 O H oil 4.1(t, J=6Hz, 2H), 7.55(S, 1H) 46 HCOCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 47 HCOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 47 HCOCH.sub.3 ( OCH.sub.2 ).sub.3 O cyclohexyl 48 HCOCH.sub.3 O(CH.sub.2).sub.3 O phenyl 68-69 49 HCOCH.sub.3 O(CH.sub.2).sub.3 O 2-pyridyl 50 HCOCH.sub.3 O(CH.sub.2).sub.4 O H oil 4.0(t, J=6Hz, 2H); 7.55(S, 1H) 51 HCOCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3 52 HCOCH.sub.3 O(CH.sub.2).sub.4 O cyclohexyl 53 HCOCH.sub.3 O(CH.sub.2).sub.4 O phenyl 92-93 54 HCOCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl 55 HCOCH.sub.3 O(CH.sub.2).sub.5 O H 56 HCOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 57 HCOCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl 58 HCOCH.sub.3 O(CH.sub.2).sub.5 O phenyl oil 4.0(t, J=6Hz, 4H); 7.55(S, 1H) 59 HCOCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl 60 HCOCH.sub.3 O(CH.sub.2).sub.6 O H 61 HCOCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 62 HCOCH.sub.3 O(CH.sub. 2).sub.6 O cyclohexyl 63 HCOCH.sub.3 O(CH.sub.2).sub.6 O phenyl 78-80 64 HCOCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl 65 HCOCH.sub.3 O(CH.sub.2).sub.8 O H oil 3.95(t, J=6Hz, 2H); 7.55(S, 1H) 66 HCOCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 67 HCOCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl 68 HCOCH.sub.3 ( OCH.sub.2).sub.8 O phenyl 69-74 69 HCOCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl 70 HCOCH.sub.3 O(CH.sub.2).sub.10 O H 71 HCOCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3 72 HCOCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl 73 HCOCH.sub.3 O(CH.sub.2).sub.10 O phenyl 49-52 74 HCOCH.sub.3 O(CH.sub.2).sub.10 O 2-pyridyl 75 HCOCH.sub.3 CH.sub.2 O CH.sub.3 76 HCOCH.sub.3 CH.sub.2 O cyclohexyl 77 HCOCH.sub.3 CH.sub.2 O phenyl 72-74 78 HCOCH.sub.3 CH.sub. 2 O pyridyl 79 HCOCH.sub.3 CH.sub.2 SCH.sub.2 phenyl oil 3.55(S, 4H); 7.55(S, 1H) 80 HCOCH.sub.3 CH.sub.2 S H 81 HCOCH.sub.3 CH.sub.2 S CH.sub.3 82 HCOCH.sub.3 CH.sub.2 S cyclohexyl 83 HCOCH.sub.3 CH.sub.2 S phenyl 69-70 84 HCOCH.sub.3 CH.sub.2 S 2-pyridyl oil 4.45(S, 2H); 7.55(S, 1H) 85 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) H 86 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) CH.sub.3 87 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl 88 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) phenyl oil 3.65(S, 3H); 3.75(S, 3H); 4.55(S, 2H) 89 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) 2-pyridyl 90 HCOCH.sub.3 O CH(CN)COCH.sub.2 H 91 HCOCH.sub.3 CH(CN)OCOCH.sub.2 CH.sub.3 92 HCOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 93 HCOCH.sub.3 CH(CN)OCOCH.sub.2 phenyl 94 HCOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 95 HCOCH.sub.3 CH(CN)OCO phenyl oil 6.7(S, 1H); 7.6(S, 1H) 96 HCOCH.sub.3 CHN H 97 HCOCH.sub.3 CHN CH.sub.3 98 HCOCH.sub.3 CHN cyclohexyl 99 HCOCH.sub.3 CHN phenyl 100 HCOCH.sub.3 CHN 2-pyridyl 101 HCOCH.sub.3 CHNOCH.sub.2 H 102 HCOCH.sub.3 CHNOCH.sub.2 CH.sub.3 103 HCOCH.sub.3 CHNOCH.sub.2 cyclohexyl 104 HCOCH.sub.3 CHNOCH.sub.2 phenyl 105 HCOCH.sub.3 CHNOCH.sub.2 2-pyridyl 106 NOCH.sub.3 CH.sub.2 CH.sub.2 H 107 NOCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 108 NOCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 109 NOCH.sub.3 CH.sub.2 CH.sub.2 phenyl 110 NOCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 111 NOCH.sub.3 CHCH H 112 NOCH.sub.3 CHCH CH.sub.3 113 NOCH.sub.3 CHCH cyclohexyl 114 NOCH.sub.3 CHCH phenyl 115 NOCH.sub.3 CHCH 2-pyridyl 116 NOCH.sub.3 OCH.sub.2 H 117 NOCH.sub.3 OCH.sub.2 CH.sub.3 118 NOCH.sub.3 OCH.sub.2 cyclohexyl 119a) NOCH.sub.3 OCH.sub.2 phenyl 62-63 non-polar isomer 3.9(S, 3H); 4.0(S, 3H); 5.05(S, 2H) 119b) NOCH.sub.3 OCH.sub.2 phenyl 63-64 polar isomer 3.85(S, 3H), 4.05(S, 3H); 5.05(S, 2H) 120 NOCH.sub.3 OCH.sub.2 2-pyridyl 121 NOCH.sub.3 OCH.sub.2 CO H 122 NOCH.sub.3 OCH.sub.2 CO CH.sub.3 123 NOCH.sub.3 OCH.sub.2 CO cyclohexyl 124 NOCH.sub.3 OCH.sub.2 CO phenyl 125 NOCH.sub.3 OCH.sub.2 CO 2-pyridyl 126 NOCH.sub.3 CH.sub.2 OCO H 127 NOCH.sub.3 CH.sub.2 OCO CH.sub.3 128 NOCH.sub.3 CH.sub.2 OCO cyclohexyl 129 NOCH.sub.3 CH.sub.2 OCO phenyl 130 NOCH.sub.3 CH.sub.2 OCO 2-pyridyl 131 NOCH.sub.3 COOCH.sub.2 H 132 NOCH.sub.3 COOCH.sub.2 CH.sub.3 133 NOCH.sub.3 COOCH.sub.2 cyclohexyl 134 NOCH.sub.3 COOCH.sub.2 phenyl 135 NOCH.sub.3 COOCH.sub.2 2-pyridyl 136 NOCH.sub.3 OCOCH.sub.2 H 137 NOCH.sub.3 OCOCH.sub.2 CH.sub.3 138 NOCH.sub.3 OCOCH.sub.2 cyclohexyl 139 NOCH.sub.3 OCOCH.sub.2 phenyl 140 NOCH.sub.3 OCOCH.sub.2 2-pyridyl 141 NOCH.sub.3 OCO phenyl 142 NOCH.sub.3 OCH.sub.2 COO CH.sub.3 143 NOCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 144 NOCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3 145 NOCH.sub.3 O(CH.sub.2).sub.2 O H 146 NOCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3 147 NOCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl 148 NOCH.sub.3 O(CH.sub.2).sub.2 O phenyl 149 NOCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl 150 NOCH.sub.3 O(CH.sub.2).sub.3 O H 151 NOCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 152 NOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 153 NOCH.sub.3 O(CH.sub.2).sub.3 O phenyl 154 NOCH.sub.3 O(CH.sub.2).sub.3 O 2-pyridyl 155 NOCH.sub.3 O(CH.sub.2).sub.4 O H 156 NOCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3 157 NOCH.sub. 3 O(CH.sub.2).sub.4 O cyclohexyl 158 NOCH.sub.3 O(CH.sub.2).sub.4 O phenyl 159 NOCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl 160 NOCH.sub.3 O(CH.sub.2).sub.5 O H 161 NOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 162 NOCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl 163 NOCH.sub.3 O(CH.sub.2).sub.5 O phenyl 164 NOCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl 165 NOCH.sub.3 O(CH.sub.2).sub.6 O H 166 NOCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 167 NOCH.sub.3 O(CH.sub.2).sub.6 O cyclohexyl 168 NOCH.sub.3 O(CH.sub.2).sub.6 O phenyl 169 NOCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl 170 NOCH.sub.3 O(CH.sub.2).sub.8 O H 171 NOCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 172 NOCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl 173 NOCH.sub.3 O(CH.sub.2).sub.8 O phenyl 174 NOCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl 175 NOCH.sub.3 O(CH.sub.2).sub.10 O H 176 NOCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3 177 NOCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl 178 NOCH.sub.3 O(CH.sub.2).sub.10 O phenyl 179 NOCH.sub.3 ( OCH.sub.2).sub.10 O 2-pyridyl 180 NOCH.sub.3 CH.sub.2 O H 181 NOCH.sub.3 CH.sub.2 O CH.sub.3 182 NOCH.sub.3 CH.sub.2 O cyclohexyl 183 NOCH.sub.3 CH.sub.2 O phenyl 184 NOCH.sub.3 CH.sub.2 O pyridyl 185 NOCH.sub.3 CH.sub.2 SCH.sub.2 H 186 NOCH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.3 187 NOCH.sub.3 CH.sub.2 SCH.sub.2 cyclohexyl 188 NOCH.sub.3 CH.sub.2 SCH.sub.2 phenyl 189 NOCH.sub.3 CH.sub.2 SCH.sub.2 2-pyridyl 190 NOCH.sub.3 CH.sub.2 N(CH.sub.3) H 191 NOCH.sub.3 CH.sub.2 N(CH.sub.3) CH.sub.3 192 NOCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl 193 NOCH.sub.3 CH.sub.2 N(CH.sub.3) phenyl 194 NOCH.sub.3 CH.sub.2 N(CH.sub. 3) 2-pyridyl 195 NOCH.sub.3 CH(CN)OCOCH.sub.2 H 196 NOCH.sub.3 CH(CN)OCOCH.s ub.2 CH.sub.3 197 NOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 198 NOCH.sub.3 CH(CN)OCOCH.sub.2 phenyl 199 NOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 200 NOCH.sub.3 CH(CN)OCO phenyl 201 NOCH.sub.3 CHN H 202 NOCH.sub.3 CHN CH.sub.3 203 NOCH.sub.3 CHN cyclohexyl 204 NOCH.sub.3 CHN phenyl 205 NOCH.sub.3 CHN 2-pyridyl 206 NOCH.sub.3 CHNOCH.sub.2 H 207 NOCH.sub.3 OC CHNH.sub.2 CH.sub.3 208 NOCH.sub.3 CHNOCH.sub.2 cyclohexyl 209 NOCH.sub.3 CHNOCH.sub.2 phenyl 210 NOCH.sub.3 CHNOCH.sub.2 2-pyridyl 211 HCCH.sub.3 CH.sub.2 CH.sub.2 H 212 HCCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 213 HCCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 214 HCCH.sub.3 CH.sub.2 CH.sub.2 phenyl 215 HCCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 216 HCCH.sub.3 CHCH H 217 HCCH.sub.3 CHCH CH.sub.3 218 HC CH.sub.3 CHCH cyclohexyl 219 HCCH.sub.3 CHCH phenyl 220 HCCH.sub.3 CHCH 2-pyridyl 221 HCCH.sub.3 OCH.sub.2 H 222 HCCH.sub.3 OCH.sub.2 CH.sub.3 223 HCCH.sub.3 OCH.sub.2 cyclohexyl 224 HCCH.sub.3 OCH.sub.2 phenyl 225 HCCH.sub.3 OCH.sub.2 2-pyridyl 226 HCCH.sub.3 OCH.sub.2 CO H 227 HCCH.sub.3 OCH.sub.2 CO CH.sub.3 228 HCCH.sub.3 OCH.sub.2 CO cyclohexyl 229 HCCH.sub.3 OCH.sub.2 C O phenyl 230 HCCH.sub.3 OCH.sub.2 CO 2-pyridyl 231 HCCH.sub.3 CH.sub.2 OCO H 232 HCCH.sub.3 CH.sub.2 OCO CH.sub.3 233 HCCH.sub.3 CH.sub.2 OCO cyclohexyl 234 HCCH.sub.3 CH.sub.2 OCO phenyl 235 HCCH.sub.3 CH.sub.2 OCO 2-pyridyl 236 HCCH.sub.3 COOCH.sub.2 H 237 HCCH.sub.3 COOCH.sub.2 CH.sub.3 238 HCCH.sub.3 COOCH.sub.2 cyclohexyl 239 HCCH.sub.3 COOCH.sub.2 phenyl 240 HCCH.sub.3 COO CH.sub.2 2-pyridyl 241 HCCH.sub.3 OCOCH.sub.2 H 242 HCCH.sub.3 OCOCH.sub.2 CH.sub.3 243 HCCH.sub.3 OCOCH.sub.2 cyclohexyl 244 HCCH.sub.3 OCOCH.sub.2 phenyl 245 HCCH.sub.3 OCOCH.sub.2 2-pyridyl 246 HCCH.sub.3 OCO phenyl 247 HCCH.sub.3 OCOCOO CH.sub.3 248 C HCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 249 HCCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 250 HCCH.sub.3 O(CH.sub.2).sub.2 O H 251 HCCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3 252 HCCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl 253 HCCH.sub.3 O(CH.sub.2).sub.2 O phenyl 254 HCCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl 255 HCCH.sub.3 O(CH.sub.2).sub.3 O H 256 C HCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 257 HCCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 258 HCCH.sub.3 O(CH.sub.2).sub.3 O phenyl 259 HCCH.sub.3 O(CH.sub.2).sub.3 O 2-pyridyl 260 HCCH.sub.3 O(CH.sub.2).sub.4 O H 261 C HCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3 262 HCCH.sub.3 O(CH.sub.2).sub.4 O cyclohexyl 263 HCCH.sub.3 O(CH.sub.2).sub.4 O phenyl 264 HCCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl 265 HCCH.sub.3 O(CH.sub.2).sub.5 O H 266 C HCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 267 HCCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl 268 HCCH.sub.3 O(CH.sub.2).sub.5 O phenyl 269 HCCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl 270 HCCH.sub.3 O(CH.sub.2).sub.6 O H 271 C HCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 272 HCCH.sub.3 O(CH.sub.2).sub.6 O cyclohexyl 273 HCCH.sub.3 O(CH.sub.2).sub.6 O phenyl 274 HCCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl 275 HCCH.sub. 3 O(CH.sub.2).sub.8 O H 276 HCCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 277 HCCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl 278 HCCH.sub.3 O(CH.sub.2).sub.8 O phenyl 279 HCCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl 280 HCCH.sub.3 O(CH.sub.2).sub.10 O H 281 HCCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3 282 HCCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl 283 HCCH.sub.3 O(CH.sub.2).sub.10 O phenyl 284 HCCH.sub.3 ( OCH.sub.2).sub.10 O 2-pyridyl 285 HCCH.sub.3 CH.sub.2 O H 286 HCCH.sub.3 CH.sub.2 O CH.sub.3 287 HCCH.sub.3 CH.sub.2 O cyclohexyl 288 HCCH.sub.3 CH.sub.2 O phenyl oil 1.75(d, J=8Hz, 3H); 3.75/S, 3H); 5.1(S, 2H) 289 HCCH.sub.3 CH.sub.2 O pyridyl 290 HCCH.sub.3 CH.sub.2 SCH.sub.2 H 291 HCCH.sub.3 CH2 SCH2 CH3 292 HCCH.sub.3 CH2SCH2 cyclohexyl 293 HCCH.sub.3 CH2SCH2 phenyl 294 HCCH.sub.3 CH2SCH2 2-pyridyl 295 HCCH.sub.3 CH2N(CH3) H 296 HCCH.sub.3 CH2N(CH3) CH3 297 HCCH.sub.3 CH2N(CH3) cyclohexyl 298 HCCH.sub.3 CH2N(CH3) phenyl 299 HCCH.sub.3 CH2N(CH3) 2-pyridyl 300 HCCH.sub.3 CH(CN)OCOCH.sub.2 H 301 HCCH.sub.3 CH(CN)OCOCH.s ub.2 CH.sub.3 302 HCCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 303 HCCH.sub.3 CH(CN)OCOCH.sub.2 phenyl 304 HCCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 305 HCCH.sub.3 CH(CN)OCO phenyl 306 HCCH.sub.3 CHN H 307 HCCH.sub.3 CHN CH.sub.3 308 HCCH.sub.3 CHN cyclohexyl 309 HCCH.sub.3 CHN phenyl 310 HCCH.sub.3 CHN 2-pyridyl 311 HCCH.sub.3 CHNOCH.sub.2 H 312 HCCH.sub.3 OC CHNH.sub.2 CH.sub.3 313 HCCH.sub.3 CHNOCH.sub.2 cyclohexyl 314 HCCH.sub.3 CHNOCH.sub.2 phenyl 315 HCCH.sub.3 CHNOCH.sub.2 2-pyridyl 316 O CH.sub.2 CH.sub.2 H 317 O CH.sub.2 CH.sub.2 CH.sub.3 318 O CH.sub.2 CH.sub.2 cyclohexyl 319 O CH.sub.2 CH.sub.2 phenyl 320 O CH.sub.2 CH.sub.2 2-pyridyl 321 O CHCH H 322 O CHCH CH.sub.3 323 O CHCH cyclohexyl 324 O CHCH phenyl 325 O CHCH 2-pyridyl 326 O OCH.sub.2 H 327 O OCH.sub.2 CH.sub.3 328 O OCH.sub.2 cyclohexyl 329 O OCH.sub.2 phenyl 330 O OCH.sub.2 2-pyridyl 331 O CH.sub.2 O H 332 O CH.sub.2 O CH.sub.3 333 O CH.sub.2 O cyclohexyl 334 O CH.sub.2 O phenyl 335 O CH.sub.2 O 2-pyridyl 336 O CH.sub.2 OCO H 337 O CH.sub.2 OCO CH.sub.3 338 O CH.sub.2 OCO cyclohexyl 339 O CH.sub.2 OCO phenyl 340 O CH.sub.2 OCO 2-pyridyl 341 NNHCH.sub.3 CH.sub.2 CH.sub.2 H 342 NNHCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 343 NNHCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 344 NNHCH.sub.3 CH.sub.2 CH.sub.2 phenyl 345 NNHCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 346 NNHCH.sub.3 CHCH H 347 NNHCH.sub.3 CHCH CH.sub.3 348 NNHCH.sub.3 CHCH cyclohexyl 349 NNHCH.sub.3 CHCH phenyl 350 NNHCH.sub.3 CHCH 2-pyridyl 351 NNHCH.sub.3 OCH.sub.2 H 352 NNHCH.sub.3 OCH.sub.2 CH.sub.3 353 NNHCH.sub.3 OCH.sub.2 cyclohexyl 354 NNHCH.sub.3 OCH.sub.2 phenyl 355 NNHCH.sub.3 OCH.sub.2 2-pyridyl 356 NNHCH.sub.3 CH.sub.2 O H 357 NNHCH.sub.3 CH.sub.2 O CH.sub.3 358 NNHCH.sub.3 CH.sub.2 O cyclohexyl 359 NNHCH.sub.3 CH.sub.2 O phenyl 360 NNHCH.sub.3 CH.sub.2 O 2-pyridyl 361 NNHCH.sub.3 CH.sub.2 OCO H 362 NNHCH.sub.3 CH.sub.2 OCO CH.sub.3 363 NNHCH.sub.3 CH.sub.2 OCO cyclohexyl 364 NNHCH.sub.3 CH.sub.2 OCO phenyl 365 NNHCH.sub.3 CH.sub.2 OCO 2-pyridyl 366 CH.sub.2 CH.sub.2 CH.sub.2 H 367 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 368 CH.sub.2 CH.sub.2 CH.sub.2 cyclohexyl 369 CH.sub.2 CH.sub.2 CH.sub.2 phenyl 370 CH.sub.2 CH.sub.2 CH.sub.2 2-pyridyl 371 CH.sub.2 CHCH H 372 CH.sub.2 CHCH CH.sub.3 373 CH.sub.2 CHCH cyclohexyl 374 CH.sub.2 CHCH phenyl 375 CH.sub.2 CHCH 2-pyridyl 376 CH.sub.2 OCH.sub.2 H 377 CH.sub.2 OCH.sub.2 CH.sub.3 378 CH.sub.2 OCH.sub.2 cyclohexyl 379 CH.sub.2 OCH.sub.2 phenyl 380 CH.sub.2 OCH.sub.2 2-pyridyl 381 CH.sub.2 CH.sub.2 O H 382 CH.sub.2 CH.sub.2 O CH.sub.3 383 CH.sub.2 CH.sub.2 O cyclohexyl 384 CH.sub.2 CH.sub.2 O phenyl 385 CH.sub.2 CH.sub.2 O 2-pyridyl 386 CH.sub.2 CH.sub.2 OCO H 387 CH.sub.2 CH.sub.2 OCO CH.sub.3 388 CH.sub.2 CH.sub.2 OCO cyclohexyl 389 CH.sub.2 CH.sub.2 O CO phenyl 390 CH.sub.2 CH.sub.2 OCO 2-pyridyl 391 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 H 392 CHCH.sub.2 CH.sub.3 CH.sub.2 C H.sub.2 CH.sub.3 393 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 394 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 phenyl 395 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 396 CHCH.sub.2 CH.sub.3 CHCH H 397 CHCH.sub.2 CH.sub.3 CHCH CH.sub.3 398 CHCH.sub.2 CH.sub.3 CHCH cyclohexyl 399 CHCH.sub.2 CH.sub.3 CHCH phenyl 400 CHCH.sub.2 CH.sub.3 CHCH 2-pyridyl 401 CHCH.sub.2 CH.sub.3 OCH.sub.2 H 402 CHCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 403 CHCH.sub.2 CH.sub.3 OCH.sub.2 cyclohexyl 404 CHCH.sub.2 CH.sub.3 OCH.sub.2 phenyl 405 CHCH.sub.2 CH.sub.3 OCH.sub.2 2-pyridyl 406 CHCH.sub.2 CH.sub.3 CH.sub.2 O H 407 CHCH.sub.2 CH.sub.3 CH.sub.2 O CH.sub.3 408 CHCH.sub.2 CH.sub.3 CH.sub.2 O cyclohexyl 409 CHCH.sub.2 CH.sub.3 CH.sub.2 O phenyl 410 CHCH.sub.2 CH.sub.3 CH.sub.2 O 2-pyridyl 411 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO H 412 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO CH.sub.3 413 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO cyclohexyl 414 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO phenyl 415 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO 2-pyridyl 416 SC CHH.sub.3 CH.sub.2 CH.sub.2 H 417 CHSCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 418 CHSCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 419 CHSCH.sub.3 CH.sub.2 CH.sub.2 phenyl 420 CHSCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 421 CHSCH.sub.3 CHCH H 422 CHSCH.sub.3 CHCH CH.sub.3 423 CHSCH.sub.3 CHCH cyclohexyl 424 CHSCH.sub.3 CHCH phenyl 425 CHSCH.sub .3 CHCH 2-pyridyl 426 CHSCH.sub.3 OCH.sub.2 H 427 CHSCH.sub.3 OCH.sub.2 CH.sub.3 428 CHSCH.sub.3 OCH.sub.2 cyclohexyl 429 CHSCH.sub.3 OCH.sub.2 phenyl 430 CHSCH.sub.3 OCH.sub.2 2-pyridyl 431 CHSCH.sub.3 CH.sub.2 O H 432 CHSCH.sub.3 CH.sub.2 O CH.sub.3 433 CHSCH.sub.3 CH.sub.2 O cyclohexyl 434 CHSCH.sub.3 CH.sub.2 O phenyl 435 CHSCH.sub.3 CH.sub.2 O 2-pyridyl 436 CHSCH.sub.3 CH.sub.2 OCO H 437 CHSCH.sub.3 CH.sub.2 OCO CH.sub.3 438 CHSCH.sub.3 CH.sub.2 OCO cyclohexyl 439 CHSCH.sub.3 CH.sub.2 OCO phenyl 440 CHSCH.sub.3 CH.sub.2 OCO 2-pyridyl 441 HCOCH.sub.3 CH.sub.2 OCO 1-(4-methoxy- 66-69 phenyl)-cyclopropyl 442 HCOCH.sub.3 CH.sub.2 OCO 2-pyridyl 70-74 443 HCOCH.sub.3 CH.sub.2 OCO 3-pyridyl 444 HCOCH.sub.3 CH.sub. 2 OCO 4-pyridyl oil 5.45(S, 2H); 7.55(S, 1H) 445 HCOCH.sub.3 CH.sub.2 OCO 1-phenyl- 79-81 cyclopropyl 446 HCOCH.sub.3 CH.sub.2 OCO 1-(4-chloro- 102-103 phenyl)-cyclopropyl 447 HCOCH.sub.3 CH.sub.2 OCO 1-Indanyl- oil 5.15(S, 2H); 7.55(S, 1H) 448 HCOCH.sub.3 CH.sub.2 OCO 4-phenyl-phenyl 132 449 HCOCH.sub.3 CH.sub.2 OCO 4-phenyl-benzyl oil 5.15(S, 2H); .55(S, 1H) 450 HCOCH.sub.3 CH.sub.2 OCO 2-phenyl-phenyl 85-87 451 HCOCH.sub.3 CH.sub.2 OCO 2-phenoxyphenyl oil 5.3(S, 2H); 7.55(S, 1H) 452 HCOCH.sub.3 CH.sub.2 OCO 2-naphthyl oil 5.45(S, 2H); 7.6(S, 1H) 453 HCOCH.sub.3 CH.sub.2 OCO 2-naphthylmethyl oil 5.15(S, 2H); 7.5(S, 1H) 454 HCOCH.sub.3 CH.sub.2 OCO 1-naphthyl 123-124 455 HCOCH.sub.3 CH.sub.2 OCO 1-naphthylmethyl oil 5.15(S, 2H); 7.55(S, 1H) 456 HCOCH.sub.3 CH.sub.2 OCO 3-phenoxyphenyl oil 5.35(S, 2H); 7.55(S, 1H) 457 HCOCH.sub.3 CH.sub.2 OCO n-heptodecyl 38-40 458 HCOCH.sub.3 CH.sub.2 OCO n-heptyl oil 5.1(S, 2H); 7.55(S, 1H) 459 HCOCH.sub.3 CH.sub.2 OCO t-butyl oil 5.1(S, 2H); 7.55(S, 1H) 460 HCOCH.sub.3 CH.sub.2 OCO iso-butyl oil 5.1(S, 2H); 7.55(S, 1H) 461 HCOCH.sub.3 CH.sub.2 OCO n-butyl oil 5.1(S, 2H); 7.55(S, 1H) 462 HCOCH.sub.3 CH.sub.2 OCO n-Propyl oil 5.1(S, 2H); 7.55(S, 1H) 463 HCOCH.sub.3 CH.sub.2 OCO Ethyl oil 5.1(S, 2H); 7.55(S, 1H) 464 HCOCH.sub.3 CH.sub.2 C OOCH.sub.2 phenyl oil 5.15(S, 2H); 7.6(S, 1H) 465 HCOCH.sub.3 CH.sub.2 OCO(CH.sub.2).sub.2 phenyl oil 5.1(S, 2H); 7.55(S, 1H) 466 HCOCH.sub.3 CH.sub.2 OCO(CH.sub.2).sub.3 phenyl oil 5.15(S, 2H); 7.55(S, 1H) 467 HCOCH.sub.3 CH.sub.2 OCO 1-methylcyclo- 45-47 propyl 468 HCOCH.sub.3 CH.sub.2 OCO n-pentyl oil 5.1(S, 2H); 7.55(S, 1H) 469 HCOCH.sub.3 CH.sub.2 OCO n-hexyl oil 5.1(S, 2H); 7.55(S, 1H) 470 HCOCH.sub.3 CH.sub.2 OCO n-nonyl oil 5.1(S, 2H); 7.55(S, 1H) 471 HCOCH.sub.3 CH.sub.2 OCO n-undecyl oil 5.1(S, 2H); 7.55(S, 1H) 472 HCOCH.sub.3 CH.sub.2 S n-octyl oil 3.7(S, 2H); 7.55(S, 1H) 473 HCOCH.sub.3 O(CH.sub.2).sub.2 phenyl oil 4.2(t, J=7Hz.2H); 7.55(S, 1H) 474 HCOCH.sub.3 O(CH.sub.2).sub. 3 phenyl oil 3.95(t, J=7Hz, 2H); 7.55(S, 1H) 475 HCOCH.sub.3 CH.sub.2 O 2-naphthyl 164-165 476 HCOCH.sub.3 OCH.sub.2 2-naphthyl 74-75 477 HCOCH.sub.3 O(CH.sub.2).sub.2 CH.sub.3 oil 3.9(t, J=8Hz, 2H); 7.55(S, 1H) 478 HCOCH.sub.3 O(CH.sub.2).sub.3 CH.sub.3 oil 3.95(t, J=8Hz, 2H); 7.55(S, 1H) 479 HCOCH.sub.3 O(CH.sub.2).sub.5 CH.sub.3 oil 3.95(t, J=7Hz, 2H); 7.55(S, 1H) 480 HCOCH.sub.3 O(CH.sub.2).sub.7 CH.sub.3 38-39 481 HCOCH.sub.3 O(CH.sub.2).sub.9 CH.sub.3 53-54 482 HCOCH.sub.3 O(CH.sub.2).sub.19 CH.sub.3 62-63 483 HCOCH.sub.3 OCH.sub.2 2,6-dimethylh eptyl oil 4.0(m, 2H); 7.55(S, 1H) 484 HCOCH.sub.3 OCH.sub.2 2,6-dimethyl- oil 4.0(m, 2H); 7.55(S, 1H) heptenyl-(5) 485 HCOCH.sub.3 OCH.sub.2 (trans)-2,6- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) dimethyl-heptadienyl-( 1,5) 486 HCOCH.sub.3 OCH.sub.2 (cis)-2,6- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) dimethyl-heptadienyl-(1,5) 487 HCOCH.sub.3 OCH.sub.2 (trans, trans)- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) (isomer mixture) 2,6,10-tri- methylundecatrienyl-(1,5,9) 488 HCOCH.sub.3 OCH.sub.2 (trans)-1,5,9,1 3- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) (isomer mixture) tetramethylpenta decen-(1) 489 HCOCH.sub.3 OCH.sub.2 1-[2-methyl-3- oil 3.75(d, J=7Hz, 2H); 7.55(S, 1H) (4-fluorophenyl]-propenyl 490 O CH.sub.2 O 2-methylphenyl oil 5.1(s, 2H) 491 O CH.sub.2 O 3-methylphenyl 492 O CH.sub.2 O 4-methylphenyl 493 O CH.sub.2 O 2,3-dimethylphenyl 494 O CH.sub.2 O 2,4-dimethylphenyl 495 O CH.sub.2 O 2,5-dimethylphenyl 496 O CH.sub.2 O 2,6-dimethylphenyl 497 O CH.sub.2 O 3,4-dimethylphenyl 498 O CH.sub.2 O 3,5-dimethylphenyl
TABLE 3__________________________________________________________________________ ##STR30##No. U A B mp NMR: .delta.(ppm)__________________________________________________________________________ 1 HCOCH.sub.3 CH.sub.2 CH.sub.2 H 2 HCOCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 3 HCOCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 4 HCOCH.sub.3 CH.sub.2 CH.sub.2 phenyl 5 HCOCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 6 HCOCH.sub.3 CHCH H 7 HCOCH.sub.3 CHCH CH.sub.3 8 HCOCH.sub.3 CHCH cyclohexyl 9 HCOCH.sub.3 CHCH 2-naphthyl 10 HCOCH.sub.3 CHCH 2-pyridyl 11 HCOCH.sub.3 OCH.sub.2 H 12 HCOCH.sub.3 OCH.sub.2 CH.sub.3 13 HCOCH.sub.3 OCH.sub.2 cyclohexyl 14 HCOCH.sub.3 OCH.sub.2 phenyl 77-79 15 HCOCH.sub.3 OCH.sub.2 2-pyridyl 16 HCOCH.sub.3 OCH.sub.2 CO H 17 HCOCH.sub.3 OCH.sub.2 CO CH.sub. 3 18 HCOCH.sub.3 OCH.sub.2 CO cyclohexyl 19 HCOCH.sub.3 OCH.sub.2 CO phenyl 20 HCOCH.sub.3 OCH.sub.2 CO 2-pyridyl 21 HCOCH.sub.3 CH.sub.2 OCO H oil 5.2(S, 2H); 7.6(S, 1H) 22 HCOCH.sub.3 CH.sub.2 OCO CH.sub.3 69-70 23 HCOCH.sub.3 CH.sub.2 OCO cyclohexyl 24 HCOCH.sub.3 CH.sub.2 OCO phenyl 74-75 25 HCOCH.sub.3 CH.sub.2 OCO 2-pyridyl 26 HCOCH.sub.3 COOCH.sub.2 H 81-84 27 HCOCH.sub.3 COOCH.sub.2 CH.sub.3 28 HCOCH.sub.3 COOCH.sub.2 cyclohexyl 29 HCOCH.sub.3 COOCH.sub.2 phenyl 30 HCOCH.sub.3 COOCH.sub.2 2-pyridyl 31 HCOCH.sub.3 OCOCH.sub.2 H 32 HCOCH.sub.3 OCOCH.sub.2 CH.sub.3 33 HCOCH.sub.3 OCOCH.sub.2 cyclohexyl 34 HCOCH.sub.3 OCOCH.sub.2 phenyl 35 HCOCH.sub.3 OCOCH.sub.2 2-pyridyl 36 HCOCH.sub.3 OCO phenyl 37 HCOCH.sub.3 OCH.sub.2 COO CH.sub.3 38 HCOCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 57-58 39 HCOCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3 44 40 HCOCH.sub.3 O(CH.sub.2).sub.2 O H 41 HCOCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3 42 HCOCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl 43 HCOCH.sub.3 O(CH.sub.2).sub.2 O phenyl 44 HCOCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl 45 HCOCH.sub.3 O(CH.sub.2).sub.3 O H 46 HCOCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 47 HCOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 47 HCOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 48 HCOCH.sub.3 O(CH.sub.2).sub.3 O phenyl 49 HCOCH.sub.3 O(CH.sub.2).sub.3 O 2-pyridyl 50 HCOCH.sub.3 O(CH.sub.2).sub.4 O H 51 HCOCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3 52 HCOCH.sub.3 O(CH.sub.2).sub. 4 O cycloheyl 53 HCOCH.sub.3 O(CH.sub.2).sub.4 O phenyl 54 HCOCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl 55 HCOCH.sub.3 O(CH.sub.2).sub.5 O H 56 HCOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 57 HCOCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl 58 HCOCH.sub.3 O(CH.sub.2).sub.5 O phenyl 59 HCOCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl 60 HCOCH.sub.3 O(CH.sub.2).sub.6 O H 61 HCOCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 62 HCOCH.sub.3 O(CH.sub.2).sub.6 O cyclohexyl 63 HCOCH.sub.3 O(CH.sub.2).sub.6 O phenyl 64 HCOCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl 65 HCOCH.sub.3 O(CH.sub.2).sub.8 O H 66 HCOCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 67 HCOCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl 68 HCOCH.sub.3 O(CH.sub.2).sub.8 O phenyl 69 HCOCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl 70 HCOCH.sub.3 O(CH.sub.2).sub.10 O H 71 HCOCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3 72 HCOCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl 73 HCOCH.sub.3 O(CH.sub.2).sub.10 O phenyl 74 HCOCH.sub.3 O(CH.sub.2).sub.10 O 2-pyridyl 75 HCOCH.sub.3 O phenyl 99-100 76 HCOCH.sub.3 CH.sub.2 O CH.sub.3 77 HCOCH.sub.3 CH.sub.2 O cyclohexyl 78 HCOCH.sub.3 CH.sub.2 O phenyl 79 HCOCH.sub.3 CH.sub.2 O pyridyl 80 HCOCH.sub.3 CH.sub.2 SCH.sub.2 H 81 HCOCH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.3 82 HCOCH.sub.3 CH.sub.2 SCH.sub.2 cyclohexyl 83 HCOCH.sub.3 CH.sub.2 SCH.sub.2 phenyl 84 HCOCH.sub.3 CH.sub.2 SCH.sub.2 2-pyridyl 85 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) H 86 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) CH.sub.3 87 HCOCH.sub. 3 CH.sub.2 N(CH.sub.3) cyclohexyl 88 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) phenyl 89 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) 2-pyridyl 90 HCOCH.sub.3 CH(CN)OCOCH.sub.2 H 91 HCOCH.sub.3 CH(CN)OCOCH.sub.2 CH.sub.3 92 HCOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 93 HCOCH.sub.3 CH(CN)OCOCH.sub.2 phenyl 94 HCOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 95 HCOCH.sub.3 CH(CN)OCO phenyl 96 HCOCH.sub.3 CHN H 97 HCOCH.sub.3 CHN CH.sub.3 98 HCOCH.sub.3 CHN cyclohexyl 99 HCOCH.sub.3 CHN phenyl100 HCOCH.sub.3 CHN 2-pyridyl101 HCOCH.sub.3 CHNOCH.sub.2 H102 HCOCH.sub.3 CHNOCH.sub.2 CH.sub.3103 HCOCH.sub.3 CHNOCH.sub.2 cyclohexyl104 HCOCH.sub.3 CHNOCH.sub.2 phenyl105 HCOCH.sub.3 CHNOCH.sub.2 2-pyridyl106 NOCH.sub.3 CH.sub.2 CH.sub.2 H107 NOCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3108 NOCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl109 NOCH.sub.3 CH.sub.2 CH.sub.2 phenyl110 NOCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl111 NOCH.sub.3 CHCH H112 NOCH.sub.3 CHCH CH.sub.3113 NOCH.sub.3 CHCH cyclohexyl114 NOCH.sub.3 CHCH phenyl115 NOCH.sub.3 CHCH 2-pyridyl116 NOCH.sub.3 OCH.sub.2 H117 NOCH.sub.3 OCH.sub.2 CH.sub.3118 NOCH.sub.3 OCH.sub.2 cyclohexyl119 NOCH.sub.3 OCH.sub.2 phenyl120 NOCH.sub.3 OCH.sub.2 2-pyridyl121 NOCH.sub.3 OCH.sub.2 CO H122 NOCH.sub.3 OCH.sub.2 CO CH.sub.3123 NOCH.sub.3 OCH.sub.2 CO cyclohexyl124 NOCH.sub.3 OCH.sub.2 CO phenyl125 NOCH.sub.3 OCH.sub.2 CO 2-pyridyl126 NOCH.sub.3 CH.sub.2 OCO H127 NOCH.sub.3 CH.sub.2 OCO CH.sub.3128 NOCH.sub.3 CH.sub.2 OCO cyclohexyl129 NOCH.sub.3 CH.sub.2 OCO phenyl130 NOCH.sub.3 CH.sub.2 OCO 2-pyridyl131 NOCH.sub.3 COOCH.sub.2 H132 NOCH.sub.3 COOCH.sub.2 CH.sub.3133 NOCH.sub.3 COOCH.sub.2 cyclohexyl134 NOCH.sub.3 COOCH.sub.2 phenyl135 NOCH.sub.3 COOCH.sub.2 2-pyridyl136 NOCH.sub.3 OCOCH.sub.2 H137 NOCH.sub.3 OCOCH.sub.2 CH.sub.3138 NOCH.sub.3 OCOCH.sub.2 cyclohexyl139 NOCH.sub.3 OCOCH.sub.2 phenyl140 NOCH.sub.3 OCOCH.sub.2 2-pyridyl141 NOCH.sub.3 OCO phenyl142 NOCH.sub.3 OCH.sub.2 COO CH.sub.3143 NOCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3144 NOCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3145 NOCH.sub.3 O(CH.sub.2).sub.2 O H146 NOCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3147 NOCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl148 NOCH.sub.3 O(CH.sub.2).sub.2 O phenyl149 NOCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl150 NOCH.sub.3 O(CH.sub.2).sub.3 O H151 NOCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3152 NOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl153 NOCH.sub.3 O(CH.sub.2).sub.3 O phenyl154 NOCH.sub. 3 O(CH.sub.2).sub.3 O 2-pyridyl155 NOCH.sub.3 O(CH.sub.2).sub.4 O H156 NOCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3157 NOCH.sub.3 O(CH.sub.2).sub.4 O cyclohexyl158 NOCH.sub.3 O(CH.sub.2).sub.4 O phenyl159 NOCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl160 NOCH.sub.3 O(CH.sub.2).sub.5 O H161 NOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3162 NOCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl163 NOCH.sub.3 O(CH.sub.2).sub.5 O phenyl164 NOCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl165 NOCH.sub.3 O(CH.sub.2).sub.6 O H166 NOCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3167 NOCH.sub.3 O(CH.sub.2).sub.6 O cyclohexyl168 NOCH.sub.3 O(CH.sub.2).sub.6 O phenyl169 NOCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl170 NOCH.sub.3 O(CH.sub.2).sub.8 O H171 NOCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3172 NOCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl173 NOCH.sub.3 O(CH.sub.2).sub.8 O phenyl174 NOCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl175 NOCH.sub.3 O(CH.sub.2).sub.10 O H176 NOCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3177 NOCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl178 NOCH.sub.3 O(CH.sub.2).sub.10 O phenyl179 NOCH.sub.3 O(CH.sub.2).sub.10 O 2-pyridyl180 NOCH.sub.3 CH.sub.2 O H181 NOCH.sub.3 CH.sub.2 O CH.sub.3182 NOCH.sub.3 CH.sub.2 O cyclohexyl183 NOCH.sub.3 CH.sub.2 O phenyl184 NOCH.sub.3 CH.sub.2 O pyridyl185 NOCH.sub.3 CH.sub.2 SCH.sub.2 H186 NOCH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.3187 NOCH.sub.3 CH.sub.2 SCH.sub.2 cyclohexyl188 NOCH.sub.3 CH.sub.2 SCH.sub.2 phenyl189 NOCH.sub.3 CH.sub.2 SCH.sub.2 2-pyridyl190 NOCH.sub.3 CH.sub.2 N(CH.sub.3) H191 NOCH.sub.3 CH.sub. 2 N(CH.sub.3) CH.sub.3192 NOCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl193 NOCH.sub.3 CH.sub.2 N(CH.sub.3) phenyl194 NOCH.sub.3 CH.sub.2 N(CH.sub.3) 2-pyridyl195 NOCH.sub.3 CH(CN)OCOCH.sub.2 H196 NOCH.sub.3 CH(CN)OCOCH.sub.2 CH.sub.3197 NOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl198 NOCH.sub.3 CH(CN)OCOCH.sub.2 phenyl199 NOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl200 NOCH.sub.3 CH(CN)OCO phenyl201 NOCH.sub.3 CHN H202 NOCH.sub.3 CHN CH.sub.3203 NOCH.sub.3 CHN cyclohexyl204 NOCH.sub.3 CHN phenyl205 NOCH.sub.3 CHN 2-pyridyl206 NOCH.sub.3 CHNOCH.sub.2 H207 NOCH.sub.3 CHNOCH.sub.2 CH.sub.3208 NOCH.sub.3 CHNOCH.sub.2 cyclohexyl209 NOCH.sub.3 CHNOCH.sub.2 phenyl210 NOCH.sub.3 CHNOCH.sub.2 2-pyridyl211 HCCH.sub.3 CH.sub.2 CH.sub.2 H212 HCCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3213 HCCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl214 HCCH.sub. 3 CH.sub.2 CH.sub.2 phenyl215 HCCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl216 HCCH.sub.3 CHCH H217 HCCH.sub.3 CHCH CH.sub.3218 HCCH.sub.3 CHCH cyclohexyl219 HCCH.sub.3 CHCH phenyl220 HCCH.sub.3 CHCH 2-pyridyl221 HCCH.sub.3 OCH.sub.2 H222 HCCH.sub.3 OCH.sub.2 CH.sub.3223 HCCH.sub.3 OCH.sub.2 cyclohexyl224 HCCH.sub.3 OCH.sub.2 phenyl225 HCCH.sub.3 OCH.sub.2 2-pyridyl226 HCCH.sub.3 OCH.sub.2 CO H227 HCCH.sub.3 OCH.sub.2 CO CH.sub.3228 HCCH.sub.3 OCH.sub.2 CO cyclohexyl229 HCCH.sub.3 OCH.sub.2 CO phenyl230 HCCH.sub.3 OCH.sub.2 CO 2-pyridyl231 HCCH.sub.3 CH.sub.2 OCO H232 HCCH.sub.3 CH.sub.2 OCO CH.sub.3233 HCCH.sub.3 CH.sub.2 OCO cyclohexyl234 HCCH.sub.3 CH.sub.2 OCO phenyl235 HCCH.sub.3 CH.sub.2 OCO 2-pyridyl236 HCCH.sub.3 COOCH.sub.2 H237 HCCH.sub.3 COOCH.sub.2 CH.sub.3238 HCCH.sub.3 COOCH.sub.2 cyclohexyl239 HCCH.sub.3 COOCH.sub.2 phenyl240 HCCH.sub.3 COOCH.sub.2 2-pyridyl241 HCCH.sub.3 OCOCH.sub.2 H242 HCCH.sub.3 OCOCH.sub.2 CH.sub.3243 HCCH.sub.3 OCOCH.sub.2 cyclohexyl244 HCCH.sub.3 OCOCH.sub.2 phenyl245 HCCH.sub.3 OCOCH.sub.2 2-pyridyl246 HCCH.sub.3 OCO phenyl247 HCCH.sub.3 OCH.sub.2 COO CH.sub.3248 HCCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3249 HCCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3250 HCCH.sub.3 O(CH.sub.2).sub.2 O H251 HCCH.sub.3 O(CH.sub.2).sub.2 O CH.sub.3252 HCCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl253 HCCH.sub.3 O(CH.sub.2).sub.2 O phenyl254 HCCH.sub.3 O(CH.sub.2).sub.2 O 2-pyridyl255 HCCH.sub.3 O(CH.sub.2).sub.3 O H256 HCCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3257 HCCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl258 HCCH.sub.3 O(CH.sub.2).sub.3 O phenyl259 HCCH.sub.3 O(CH.sub.2).sub.3 O 2-pryidyl260 HCCH.sub.3 O(CH.sub.2).sub.4 O H261 HCCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3262 HCCH.sub.3 O(CH.sub.2).sub.4 O cyclohexyl263 HCCH.sub.3 O(CH.sub.2).sub.4 O phenyl264 HCCH.sub.3 O(CH.sub.2).sub.4 O 2-pyridyl265 HCCH.sub.3 O(CH.sub.2).sub.5 O H266 HCCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3267 HCCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl268 HCCH.sub.3 O(CH.sub.2).sub.5 O phenyl269 HCCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl270 HCCH.sub.3 O(CH.sub.2).sub.6 O H271 HCCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3272 HCCH.sub. 3 O(CH.sub.2).sub.6 O cyclohexyl273 HCCH.sub.3 O(CH.sub.2).sub.6 O phenyl274 HCCH.sub.3 O(CH.sub.2).sub.6 O 2-pyridyl275 HCCH.sub.3 O(CH.sub.2).sub.8 O H276 HCCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3277 HCCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl278 HCCH.sub.3 O(CH.sub.2).sub.8 O phenyl279 HCCH.sub.3 O(CH.sub.2).sub.8 O 2-pyridyl280 HCCH.sub.3 O(CH.sub.2).sub.10 O H281 HCCH.sub.3 O(CH.sub.2).sub.10 O CH.sub.3282 HCCH.sub.3 O(CH.sub.2).sub.10 O cyclohexyl283 HCCH.sub.3 O(CH.sub.2).sub.10 O phenyl284 HCCH.sub.3 O(CH.sub.2).sub.10 O 2-pyridyl285 HCCH.sub.3 CH.sub.2 O H286 HCCH.sub.3 CH.sub.2 O CH.sub.3287 HCCH.sub.3 CH.sub.2 O cyclohexyl288 HCCH.sub.3 CH.sub.2 O phenyl289 HCCH.sub.3 CH.sub.2 O pyridyl290 HCCH.sub.3 CH.sub.2 SCH.sub.2 H291 HCCH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.3292 HCCH.sub.3 CH.sub.2 SCH.sub.2 cyclohexyl293 HCCH.sub.3 CH.sub.2 SCH.sub.2 phenyl294 HCCH.sub.3 CH.sub.2 SCH.sub.2 2-pyridyl295 HCCH.sub.3 CH.sub.2 N(CH.sub.3) H296 HCCH.sub.3 CH.sub.2 N(CH.sub.3) CH.sub.3297 HCCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl298 HCCH.sub.3 CH.sub.2 N(CH.sub.3) phenyl299 HCCH.sub.3 CH.sub.2 N(CH.sub.3) 2-pyridyl300 HCCH.sub.3 CH(CN)OCOCH.sub.2 H301 HCCH.sub.3 CH(CN)OCOCH.sub.2 CH.sub.3302 HCCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl303 HCCH.sub.3 CH(CN)OCOCH.sub.2 phenyl304 HCCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl305 HCCH.sub.3 CH(CN)OCO phenyl306 HCCH.sub.3 CHN H307 HCCH.sub.3 CHN CH.sub.3308 HCCH.sub.3 CHN cyclohexyl309 HCCH.sub.3 CHN phenyl310 HCCH.sub.3 CHN 2-pyridyl311 HCCH.sub.3 CHNOCH.sub.2 H312 HCCH.sub.3 CHNOCH.sub.2 CH.sub.3313 HCCH.sub.3 CHNOCH.sub.2 cyclohexyl314 HCCH.sub.3 CHNOCH.sub.2 phenyl315 HCCH.sub.3 CHNOCH.sub.2 2-pyridyl316 O CH.sub.2 CH.sub.2 H317 O CH.sub.2 CH.sub.2 CH.sub.3318 O CH.sub.2 CH.sub.2 cyclohexyl319 O CH.sub.2 CH.sub.2 phenyl320 O CH.sub.2 CH.sub.2 2-pyridyl312 O CHCH H322 O CHCH CH.sub.3323 O CHCH cyclohexyl324 O CHCH phenyl325 O CHCH 2-pyridyl326 O OCH.sub.2 H327 O OCH.sub.2 CH.sub.3328 O OCH.sub.2 cyclohexyl329 O OCH.sub.2 phenyl330 O OCH.sub.2 2-pyridyl331 O CH.sub.2 O H332 O CH.sub.2 O CH.sub.3333 O CH.sub.2 O cyclohexyl334 O CH.sub.2 O phenyl335 O CH.sub.2 O 2-pyridyl336 O CH.sub. 2 OCO H337 O CH.sub.2 OCO CH.sub.3338 O CH.sub.2 OCO cyclohexyl339 O CH.sub.2 OCO phenyl340 O CH.sub.2 OCO 2-pyridyl341 NNHCH.sub.3 CH.sub.2 CH.sub.2 H342 NNHCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3343 NNHCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl344 NNHCH.sub.3 CH.sub.2 CH.sub.2 phenyl345 NNHCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl346 NNHCH.sub.3 CHCH H347 NNHCH.sub.3 CHCH CH.sub.3348 NNHCH.sub.3 CHCH cyclohexyl349 NNHCH.sub.3 CHCH phenyl350 NNHCH.sub.3 CHCH 2-pyridyl351 NNHCH.sub.3 OCH.sub.2 H352 NNHCH.sub.3 OCH.sub.2 CH.sub.3353 NNHCH.sub.3 OCH.sub.2 cyclohexyl354 NNHCH.sub.3 OCH.sub.2 phenyl355 NNHCH.sub.3 OCH.sub.2 2-pyridyl356 NNHCH.sub.3 CH.sub.2 O H357 NNHCH.sub.3 CH.sub.2 O CH.sub.3358 NNHCH.sub.3 CH.sub.2 O cyclohexyl359 NNHCH.sub.3 CH.sub.2 O phenyl360 NNHCH.sub.3 CH.sub.2 O 2-pyridyl361 NNHCH.sub.3 CH.sub.2 OCO H362 NNHCH.sub.3 CH.sub.2 OCO CH.sub.3363 NNHCH.sub.3 CH.sub.2 OCO cyclohexyl364 NNHCH.sub.3 CH.sub.2 OCO phenyl365 NNHCH.sub.3 CH.sub.2 OCO 2-pyridyl366 CH.sub.2 CH.sub.2 CH.sub.2 H367 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3368 CH.sub.2 CH.sub.2 CH.sub.2 cyclohexyl369 CH.sub.2 CH.sub.2 CH.sub.2 phenyl370 CH.sub.2 CH.sub.2 CH.sub.2 2-pyridyl371 CH.sub.2 CHCH H372 CH.sub.2 CHCH CH.sub.3373 CH.sub.2 CHCH cyclohexyl374 CH.sub.2 CHCH phenyl375 CH.sub.2 CHCH 2-pyridyl376 CH.sub.2 OCH.sub.2 H377 CH.sub.2 OCH.sub.2 CH.sub.3378 CH.sub.2 OCH.sub.2 cyclohexyl379 CH.sub.2 OCH.sub.2 phenyl380 CH.sub.2 OCH.sub.2 2-pyridyl381 CH.sub.2 CH.sub.2 O H382 CH.sub.2 CH.sub.2 O CH.sub.3383 CH.sub.2 CH.sub.2 O cyclohexyl384 CH.sub.2 CH.sub.2 O phenyl385 CH.sub.2 CH.sub.2 O 2-pyridyl386 CH.sub.2 CH.sub.2 OCO H387 CH.sub.2 CH.sub.2 OCO CH.sub.3388 CH.sub.2 CH.sub.2 OCO cyclohexyl389 CH.sub.2 CH.sub.2 OCO phenyl390 CH.sub.2 CH.sub.2 OCO 2-pyridyl391 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 H392 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3393 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl394 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 phenyl395 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl396 CHCH.sub.2 CH.sub.3 CHCH H397 CHCH.sub.2 CH.sub.3 CHCH CH.sub.3398 CHCH.sub.2 CH.sub.3 CHCH cyclohexyl399 CHCH.sub.2 CH.sub.3 CHCH phenyl400 CHCH.sub.2 CH.sub.3 CHCH 2-pyridyl401 CHCH.sub.2 CH.sub.3 OCH.sub.2 H402 CHCH.sub.2 CH.sub.3 OCH.sub. 2 CH.sub.3403 CHCH.sub.2 CH.sub.3 OCH.sub.2 cyclohexyl404 CHCH.sub.2 CH.sub.3 OCH.sub.2 phenyl405 CHCH.sub.2 CH.sub.3 OCH.sub.2 2-pyridyl406 CHCH.sub.2 CH.sub.3 CH.sub.2 O H407 CHCH.sub.2 CH.sub.3 CH.sub.2 O CH.sub.3408 CHCH.sub.2 CH.sub.3 CH.sub.2 O cyclohexyl409 CHCH.sub.2 CH.sub.3 CH.sub.2 O phenyl410 CHCH.sub.2 CH.sub.3 CH.sub.2 O 2-pyridyl411 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO H412 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO CH.sub.3413 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO cyclohexyl414 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO phenyl415 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO 2-pyridyl416 CHSCH.sub.3 CH.sub.2 CH.sub.2 H417 CHSCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3418 CHSCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl419 CHS CH.sub.3 CH.sub.2 CH.sub.2 phenyl420 CHSCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl421 CHSCH.sub.3 CHCH H422 CHSCH.sub.3 CHCH CH.sub.3423 CHSCH.sub.3 CHCH cyclohexyl424 CHSCH.sub.3 CHCH phenyl425 CHSCH.sub.3 CHCH 2-pyridyl426 CHSCH.sub.3 OCH.sub.2 H427 CHSCH.sub.3 OCH.sub.2 CH.sub.3428 CHSCH.sub.3 OCH.sub.2 cyclohexyl429 CHSCH.sub.3 OCH.sub.2 phenyl430 CHSCH.sub.3 OCH.sub.2 2-pyridyl431 CHSCH.sub.3 CH.sub.2 O H432 CHSCH.sub.3 CH.sub.2 O CH.sub.3433 CHSCH.sub.3 CH.sub.2 O cyclohexyl434 CHSCH.sub.3 CH.sub.2 O phenyl435 CHSCH.sub.3 CH.sub.2 O 2-pyridyl436 CHSCH.sub.3 CH.sub.2 OCO H437 CHSCH.sub.3 CH.sub.2 OCO CH.sub.3438 CHSCH.sub.3 CH.sub.2 OCO cyclohexyl439 CHSCH.sub.3 CH.sub.2 O CO phenyl440 CHSCH.sub.3 CH.sub.2 OCO 2-pyridyl441 HCOCH.sub.3 CH.sub.2 OCO n-heptadecyl 37-38442 HCOCH.sub.3 CH.sub.2 OCO n-heptyl oil 5.1(S, 2H); 7.55(S, 1H)443 HCOCH.sub.3 CH.sub.2 OCO t-butyl oil 5.1(S, 2H); 7.6(S, 1H)444 HCOCH.sub.3 CH.sub.2 OCO iso-butyl oil 5.1(S, 2H); 7.55(S, 1H)445 HCOCH.sub.3 CH.sub.2 OCO n-butyl oil 5.1(S, 2H); 7.55(S, 1H)446 HCOCH.sub.3 CH.sub.2 OCO n-propyl oil 5.1(S, 2H); 7.55(S, 1H)447 HCOCH.sub.3 CH.sub.2 OCO n-ethyl oil 5.1(S, 2H); 7.55(S, 1H)448 HCOCH.sub.3 CH.sub.2 OCOCH.sub.2 phenyl 59-60449 HCOCH.sub.3 CH.sub.2 OCO(CH.sub.2).sub.2 phenyl oil 5.1(S, 2H); 7.55(S, 1H)450 HCOCH.sub.3 CH.sub.2 OCO(CH.sub.2).sub.3 phenyl oil 5.1(S, 2H); 7.55(S, 1H)451 HCOCH.sub.3 O(CH.sub.2).sub.2 O A oil 4.1(t, J=5Hz, 2H); 7.55(S, 1H)452 HCOCH.sub.3 O(CH.sub.2).sub.3 O H oil 4.1(t, J=6Hz, 2H); 7.55(S, 1H)453 HCOCH.sub.3 O(CH.sub.2).sub. 4 O H oil 4.0(t, J=6Hz, 2H); 7.55(S, 1H)454 HCOCH.sub.3 O(CH.sub.2).sub.8 O H 54-55__________________________________________________________________________
TABLE 4______________________________________ ##STR31##No. X.sub.m mp NMR: .delta.(ppm)______________________________________ 1 2-F oil 5.15(S, 2H); 7.55(S, 1H) 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.5 7 2,3-F.sub.2 8 2-Cl oil 5.15(S, 2H); 7.55(S, 1H) 9 3-Cl oil 5.05(S, 2H); 7.55(S, 1H) 10 4-Cl 64-67 11 2,3-Cl.sub.2 106-108 12 2,4-Cl.sub.2 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2205 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-J 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65 2-CH.sub.3 78-79 66 3-CH.sub.3 88-90 67 4-CH.sub.3 116-118 68 2,3-(CH.sub.3).sub.2 69-71 69 2,4-(CH.sub.3).sub.2 79-82 70 2,5-(CH.sub.3).sub.2 82-84 71 2,6-(CH.sub.3).sub.2 59-61 72 3,4-(CH.sub.3).sub.2 83-84 73 3,5-(CH.sub.3).sub.2 76-77 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,3,6-(CH.sub.3).sub.3 79 2,3,4-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub. 2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl)117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 C.sub.6 H.sub.5137 3-CH.sub.2 C.sub.6 H.sub.5138 4-CH.sub.2 C.sub.6 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5 149-150144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3 oil 5.15(S, 2H); 7.55(S, 1H)159 3-OCH.sub.3 oil 5.05(S, 2H); 7.55(S, 1H)200 4-OCH.sub.3 107-109161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3 oil 5.2(S, 2H); 7.55(S, 1H)184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.2, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3 oil 5.1(s, 2H); 7.6(s, 1H)262 3-CHNOCH.sub.3 65-68263 4-CHNOCH.sub.3 69-72264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub. 13) oil 5.1(s, 2H); 7.6(s, 1H)274 3-CHNO(n-C.sub.6 H.sub.13) oil 5.1(s, 2H); 7.6(s, 1H)275 4-CHNO(n-C.sub.6 H.sub.13) oil 5.1(s, 2H); 7.6(s, 1H)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5) oil 5.1(s, 2H). 7.55(s, 1H)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5) oil 5.1(s, 2H); 7.6(s, 1H)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5) 93-96282 2-CO.sub.2 CH.sub.3 65-66283 3-CO.sub.2 CH.sub.3 69-72284 4-CO.sub.2 CH.sub.3 106-107285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2 oil 5.1(s, 2H); 7.6(s, 1H)301 3-CHNOCH.sub.2 CHCH.sub.2 oil 5.1(s, 2H); 7.6(s, 1H)302 4-CHNOCH.sub.2 CHCH.sub.2 oil 5.1(s, 2H); 7.6(s, 1H)303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.17)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO 95-96331 3-CHO332 4-CHO 123-125333 2-CH.sub.3 -4-CHNO-allyl oil 5.1(s, 2H); 7.55(s, 1H)334 2-CH.sub.3 -5-CHNO-allyl oil 5.1(s, 2H); 7.6(s, 1H)335 2-CH.sub.3 -6-CHNO-allyl oil 4.85(s, 2H); 7.6(s, 1H)336 3-CH.sub.3 -6-CHNO-allyl 97-98337 4-CH.sub.3 -6-CHNO-allyl oil 5.05(s, 2H); 7.6(s, 1H)______________________________________
TABLE 5______________________________________ ##STR32##No. X.sub.m mp NMR: .delta. (ppm)______________________________________ 1 2-F 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.5 7 2,3-F.sub.2 8 2-Cl 9a) 3-Cl; oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.05(s, 2H) 9b 3-Cl; 82-85 polar isomer 10 4-Cl 11 2,3-Cl.sub.2 12 2,4-Cl.sub.2 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65a) 2-CH.sub.3 :non-polar oil 3.95(S, 3H); 4.05(S, 3H); isomer 5.05(S, 2H) 65b) 2-CH.sub.3 :polar isomer 99-100 66a) 3-CH.sub.3 :non-polar oil 3.9(S, 3H); 4.0(S, 3H); isomer 5.05(S, 2H) 66b) 3-CH.sub.3 :polar isomer 51-54 67a) 4-CH.sub.3 :non-polar oil 3.9(S, 3H); 4.0(S, 3H); isomer 5.0(S, 2H) 67b) 4-CH.sub.3 :polar isomer 102-103 68a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 2,3-(CH.sub.3 ).sub.2 5.05(s, 2H) 68b) polar isomer; 86-89 2,3-(CH.sub.3).sub.2 69a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 2,4-(CH.sub.3).sub.2 5.05(s, 2H) 69b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H); 2,4-(CH.sub.3).sub.2 5.05(s, 2H) 70a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 2,5-(CH.sub.3).sub.2 5.05(s, 2H) 70b) polar isomer; 85-88 2,5-(CH.sub.3).sub.2 71a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 2,6-(CH.sub.3).sub.2 4.80(s, 2H) 71b) polar isomer; 79-81 2,6-(CH.sub.3).sub.2 72a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 3,4-(CH.sub.3).sub.2 5.05(s, 2H) 72b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H); 3,4-(CH.sub.3).sub.2 5.05(s, 2H) 73a) non-polar isomer; oil 3.95(s, 3H); 4.05(s, 3H); 3,5-(CH.sub.3).sub.2 5.05(s, 2H) 73b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H); 3,5-(CH.sub.3).sub.2 5.05(s, 2H) 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6,-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-S-C.sub.4 H.sub.9101 3-S-C.sub.4 H.sub.9102 4-S-C.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethyl- butyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2, C.sub.6 H.sub.5137 3-CH.sub.2, C.sub.6 H.sub.5138 4-CH.sub.2, C.sub.6 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub. 3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158a) 2-OCH.sub.3 ; oil 3.85; 3.90; 5.0(3s, 3H non-polar isomer in each case); 5.1(s, 2H)158b) 2-OCH.sub.3 63-67 polar isomer159a) 3-OCH.sub.3 ; oil 3.80; 3,95; 4.05(3s, 3H non-polar isomer in each case); 5.1(s, 2H)159b) 3-OCH.sub.3 35 polar isomer160a) 4-OCH.sub.3 ; oil 3.75; 3.95; 4.05(3s, 3H non-polar isomer in each case); 5.05(s, 2H)160b) 4-OCH.sub.3 75-78 polar isomer161 3-OC.sub.2 H.sub.5162 3-O-C.sub.2 H.sub.5163 4-O-C.sub.2 H.sub.7164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-O-CH.sub.2 C.sub.6 H.sub.5177 3-O-CH.sub.2 C.sub.6 H.sub.5178 4-O-CH.sub.2 C.sub.6 H.sub.5179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub. 3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 3-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.2, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3 ;264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270a) 2-CHNO(n-C.sub.4 H.sub.9); oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)270b) 2-CHNO(n-C.sub.4 H.sub.9): oil 3.90(s, 3H); 4.05(s, 3H); polar isomer 5.1(s, 2H)271a) 3-CHNO(n-C.sub.4 H.sub.9): oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)271b) 3-CHNO(n-C.sub.4 H.sub.9): oil 3.90(s, 3H); 4.05(s, 3H); polar isomer 5.1(s, 2H)272a) 4-CHNO(n-C.sub.4 H.sub.9): oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.05(s, 2H)272b) 4-CHNO(n-C.sub.4 H.sub.9): 88-89 polar isomer273a) 2-CHNO(n-C.sub.6 H.sub.13): oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)273b) 2-CHNO(n-C.sub.6 H.sub.13): oil 3.90(s, 3H); 4.05(s, 3H); polar isomer 5.1(s, 2H)274a) 3-CHNO(n-C.sub.6 H.sub.13): oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)274b) 3-CHNO(n-C.sub.6 H.sub.13): oil 3.90(s, 3H); 4.05(s, 3H); polar isomer 5.1(s, 2H)275a) 4-CHNO(n-C.sub.6 H.sub.13): oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)275b) 4-CHNO(n-C.sub.6 H.sub.13): 77-80 polar isomer276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub. 2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300a) 2-CHNO-allyl: oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)300b) 2-CHNO-allyl: oil 3.90(s, 3H); 4.10(s, 3H); polar isomer 5.1(s, 2H)301a) 3-CHNO-allyl: oil 3.95(s, 3H); 4.05(s, 3H); non-polar isomer 5.1(s, 2H)301b) 3-CHNO-allyl: oil 3.90(s, 3H); 4.05(s, 3H); polar isomer 5.1(s, 2H)302a) 4-CHNO-allyl: oil 3.90(s, 3H); 4.0(s, 3H); non-polar isomer 5.1(s, 2H)302b) 4-CHNO-allyl: 89 polar isomer303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 2-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 6______________________________________ ##STR33##No. X.sub.m mp NMR: .delta.(ppm)______________________________________ 1 2-F 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.5 7 2,3-F.sub.2 8 2-Cl 9 3-Cl 10 4-Cl 11 2,3-Cl.sub.2 12 2,4-Cl.sub.2 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65 2-CH.sub.3 oil 1.75(d, J=8Hz, 3H); 3.7(S, 3H); 5.1(S, 2H) 66 3-CH.sub.3 67 4-CH.sub.3 68 2,3-(CH.sub.3).sub.2 69 2,4-(CH.sub.3).sub.2 70 2,5-(CH.sub.3).sub.2 71 2,6-(CH.sub.3).sub.2 72 3,4-(CH.sub.3).sub.2 73 3,5-(CH.sub.3).sub.2 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub. 3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub. 4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 C.sub.6 H.sub.5137 3-CH.sub.2 C.sub.6 H.sub.5138 4-CH.sub.2 C.sub.6 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub. 5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub. 8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2301 3-CHNOCH.sub.2 CHCH.sub.2302 4-CHNOCH.sub.2 CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub. 2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 7______________________________________ ##STR34##No. X.sub.m mp NMR: .delta.(ppm)______________________________________ 1 2-F 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.4 7 2,3-F.sub.2 8 2-Cl 72-74 9 3-Cl oil 5.0(S, 2H); 7.55(S, 1H) 10 4-Cl 80-81 11 2,3-Cl.sub.2 12 2,4-Cl.sub.2 59-61 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 oil 5.0(S, 2H); 7.55(S, 1H) 16 3,5-Cl.sub.2 93-95 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65 2-CH.sub.3 oil 5.0(S, 2H); 7.55(S, 1H) 66 3-CH.sub.3 oil 5.0(S, 2H); 7.55(S, 1H) 67 4-CH.sub.3 69-71 68 2,3-(CH.sub.3).sub.2 69 2,4-(CH.sub.3).sub.2 70 2,5-(CH.sub.3).sub.2 71 2,6-(CH.sub.3).sub.2 72 3,4-(CH.sub.3).sub.2 73 3,5-(CH.sub.3).sub.2 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub. 3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-S-C.sub.4 H.sub.9101 3-S-C.sub.4 H.sub.9102 4-S-C.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 C.sub.6 H.sub.5137 3-CH.sub.2 C.sub.6 H.sub.5138 4-CH.sub.2 C.sub.2 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-i-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 3-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-J.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2301 3-CHNOCH.sub.2 CHCH.sub.2302 4-CHNOCH.sub.2 CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub. 6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.17)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO333 3-benzoyl oil 5.15(s, 2H); 7.55 (s, 1H)______________________________________
TABLE 8__________________________________________________________________________ ##STR35##No. X.sub.m mp NMR: .delta. (ppm)__________________________________________________________________________ 1a) 2-F: non-polar isomer oil 3.9(S, 3H); 4.0(S, 3H); 5.15(S, 2H) 1b) 2-F: polar isomer 77-79 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.5 7 2,3-F.sub.2 8a) 2-Cl: non-polar isomer oil 3.9(S, 3H); 4.0(S, 3H); 5.15(S, 2H) 8b) 2-Cl: polar isomer 78-80 9a) 3-Cl: non-polar isomer oil 3.9(S, 3H); 4.0(S, 3H); 5.05(S, 2H) 9b) 3-Cl: polar isomer 64-66 10a) 4-Cl: non-polar isomer 58-70 3.9(S, 3H); 4.0(S, 3H); 5.0(S, 2H) 10b) 4-Cl: polar isomer 112-120 3.85(S, 3H); 4.05(S, 3H); 5.0(S, 2H) 11 2,3-Cl.sub.2 12a) 2,4-Cl.sub.2 : non-polar isomer 89-93 12b) 2,4-Cl.sub.2 : polar isomer 83-86 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65a) 2-CH.sub.3 : non-polar isomer 51-53 65b) 2-CH.sub.3 : polar isomer 79-83 66a 3-CH.sub.3 : non-polar isomer oil 3.9(s, 3H); 4.0(s, 3H); 5.0(s, 2H) 66b 3-CH.sub.3 : polar isomer 87-89 67a 4-CH.sub.3 : non-polar isomer oil 3.95(s, 3H); 4.05(s, 3H); 5.05(s, 2H) 67b 3-CH.sub.3 : polar isomer 78-79 68 2,3-(CH.sub.3).sub.2 69 2,4-(CH.sub.3).sub.2 70 2,5-(CH.sub.3).sub.2 71 2,6-(CH.sub.3).sub.2 72 3,4-(CH.sub.3).sub.2 73 3,5-(CH.sub.3).sub.2 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub. 2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-S-C.sub.4 H.sub.9101 3-S-C.sub.4 H.sub.9102 4-S-C.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 C.sub.6 H.sub.5137 3-CH.sub.2 C.sub.6 H.sub.5138 4-CH.sub.2 C.sub.2 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5 , 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159a 3-OCH.sub.3 : oil 3.80; 3, 95, 4.05(3s, 3H non-polar isomer in each case); 5.05(s, 2H)159b 3-OCH.sub.3 : oil 3.80; 3.90, 4.05(3s, 3H polar isomer in each case); 5.05(s, 2H)160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-O-C.sub.2 H.sub.5163 4-O-C.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-O-CH.sub.2 C.sub.6 H.sub.5177 3-O-CH.sub.2 C.sub.6 H.sub.5178 4-O-CH.sub.2 C.sub.6 H.sub. 5179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub. 3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub. 2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub. 7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2301 3-CHNOCH.sub.2 CHCH.sub.2302 4-CHNOCH.sub.2 CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7 )315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO__________________________________________________________________________
TABLE 9______________________________________ ##STR36##No. X.sub.m mp NMR: .delta. (ppm)______________________________________ 1 2-F 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6,-F.sub.5 7 2,3-F.sub.2 8 2-Cl 9 3-Cl 10 4-Cl 11 2,3-Cl.sub.2 12 2,4-Cl.sub.2 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6,-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65 2-CH.sub.3 66 3-CH.sub.3 67 4-CH.sub.3 68 2,3-(CH.sub.3).sub.2 69 2,4-(CH.sub.3).sub.2 70 2,5-(CH.sub.3).sub.2 71 2,6-(CH.sub.3).sub.2 72 3,4-(CH.sub.3).sub.2 73 3,5-(CH.sub.3).sub.2 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3 ).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-S-C.sub.4 H.sub.9101 3-S-C.sub.4 H.sub.9102 4-S-C.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 -C.sub.6 H.sub.5137 3-CH.sub.2 -C.sub.6 H.sub.5138 4-CH.sub.2 -C.sub.2 H.sub.5139 2-CH.sub.2 -C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 -C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 -C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 5-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-O-C.sub.2 H.sub.5163 4-O-C.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-O-CH.sub.2 C.sub.6 H.sub.5177 3-O-CH.sub.2 C.sub.6 H.sub.5178 4-O-CH.sub.2 C.sub.6 H.sub.5179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3)62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2 , 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2301 3-CHNOCH.sub.2 CHCH.sub.2302 4-CHNOCH.sub.2 CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 10______________________________________ ##STR37##No. X.sub.m mp NMR: .delta. (ppm)______________________________________1 2-F2 3-F3 4-F4 2,4-F.sub.25 2,4,6-F.sub.36 2,3,4,5,6-F.sub.57 2,3-F.sub.28 2-Cl9 3-Cl10 4-Cl11 2,3-Cl.sub.212 2,4-Cl.sub.213 2,5-Cl.sub.214 2,6-Cl.sub.215 3,4-Cl.sub.216 3,5-Cl.sub.217 2,3,4-Cl.sub.318 2,3,5-Cl.sub.319 2,3,6-Cl.sub.320 2,4,5-Cl.sub.321 2,4,6-Cl.sub.322 3,4,5-Cl.sub.323 2,3,4,6-Cl.sub.424 2,3,5,6-Cl.sub.425 2,3,4,5,6-Cl.sub.526 2-Br27 3-Br28 4-Br29 2,4-Br.sub.230 2,5-Br.sub.531 2,6-Br.sub.232 2,4,6-Br.sub.333 2,3,4,5,6-Br.sub.534 2-I35 3-I36 4-I37 2,4-I.sub.238 2-Cl, 3-F39 2-Cl, 4-F40 2-Cl, 5-F41 2-Cl, 6-F42 2-Cl, 3-Br43 2-Cl, 4-Br44 2-Cl, 6-Br45 2-Cl, 6-Br46 2-Br, 3-Cl47 2-Br, 4-Cl48 2-Br, 5-Cl49 2-Br, 3-F50 2-Br, 4-F51 2-Br, 5-F52 2-Br, 6-F53 2-F, 3-Cl54 2-F, 4-Cl55 2-F, 5-Cl56 3-Cl, 4-F57 3-Cl, 5-F58 3-Cl, 4-Br59 3-Cl, 5-Br60 3-F, 4-Cl61 3-F, 4-Br62 3-Br, 4-Cl63 3-Br, 4-F64 2,6-Cl.sub.2, 4-Br65 2-CH.sub.366 3-CH.sub.367 4-CH.sub.368 2,3-(CH.sub.3).sub.269 2,4-(CH.sub.3).sub.270 2,5-(CH.sub.3).sub.271 2,6-(CH.sub.3).sub.272 3,4-(CH.sub.3).sub.273 3,5-(CH.sub.3).sub.274 3,5-(CH.sub.3).sub.275 2,3,4-(CH.sub.3).sub.376 2,3,6-(CH.sub.3).sub.377 2,4,5-(CH.sub.3).sub.378 2,4,6-(CH.sub.3).sub.379 3,4,5-(CH.sub.3).sub.380 2,3,4,6-(CH.sub.3).sub.481 2,3,5,6-(CH.sub.3).sub.482 2,3,4,5,6-(CH.sub.3).sub.583 2-C.sub.2 H.sub.584 3-C.sub.2 H.sub.585 4-C.sub.2 H.sub.586 2,4-(C.sub.2 H.sub.5).sub.287 2,6-(C.sub.2 H.sub.5).sub.288 3,5-(C.sub.2 H.sub.5).sub.289 2,4,6-(C.sub.2 H.sub.5).sub.390 2-n-C.sub.3 H.sub.791 3-n-C.sub.3 H.sub.792 4-n-C.sub.3 H.sub.793 2-i-C.sub.3 H.sub.794 3-i-C.sub.3 H.sub.795 4-i-C.sub.3 H.sub.796 2,4-(i-C.sub.3 H.sub.7).sub.297 2,6-(i-C.sub.3 H.sub.7).sub. 298 3,5-(i-C.sub.3 H.sub.7).sub.299 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2C.sub.6 H.sub.5137 3-CH.sub.2C.sub.6 H.sub.5138 4-CH.sub.2C.sub.6 H.sub.5139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub. 3 H.sub.7)273 2-CHNO(i-C.sub.6 H.sub.13)274 3-CHNO(i-C.sub.6 H.sub.13)275 4-CHNO(i-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (i-C.sub.6 H.sub.13)295 3-CO.sub.2 (i-C.sub.6 H.sub.13)296 4-CO.sub.2 (i-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2CHCH.sub.2301 3-CHNOCH.sub.2CHCH.sub.2302 4-CHNOCH.sub.2CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 11______________________________________ ##STR38##No. X.sub.m mp NMR: .delta. (ppm)______________________________________1 2-F2 3-F3 4-F4 2,4-F.sub.25 2,4,6-F.sub.36 2,3,4,5,6-F.sub.57 2,3-F.sub.28 2-Cl9 3-Cl10 4-Cl11 2,3-Cl.sub.212 2,4-Cl.sub.213 2,5-Cl.sub.214 2,6-Cl.sub.215 3,4-Cl.sub.216 3,5-Cl.sub.217 2,3,4-Cl.sub.318 2,3,5-Cl.sub.319 2,3,6-Cl.sub.320 2,4,5-Cl.sub.321 2,4,6-Cl.sub.322 3,4,5-Cl.sub.323 2,3,4,6-Cl.sub.424 2,3,5,6-Cl.sub.425 2,3,4,5,6-Cl.sub.526 2-Br27 3-Br28 4-Br29 2,4-Br.sub.230 2,5-Br.sub.531 2,6-Br.sub.232 2,4,6-Br.sub.333 2,3,4,5,6-Br.sub.534 2-I35 3-I36 4-I37 2,4-I.sub.238 2-Cl, 3-F39 2-Cl, 4-F40 2-Cl, 5-F41 2-Cl, 6-F42 2-Cl, 3-Br43 2-Cl, 4-Br44 2-Cl, 6-Br45 2-Cl, 6-Br46 2-Br, 3-Cl47 2-Br, 4-Cl48 2-Br, 5-Cl49 2-Br, 3-F50 2-Br, 4-F51 2-Br, 5-F52 2-Br, 6-F53 2-F, 3-Cl54 2-F, 4-Cl55 2-F, 5-Cl56 3-Cl, 4-F57 3-Cl, 5-F58 3-Cl, 4-Br59 3-Cl, 5-Br60 3-F, 4-Cl61 3-F, 4-Br62 3-Br, 4-Cl63 3-Br, 4-F64 2,6-Cl.sub.2, 4-Br65 2-CH.sub.366 3-CH.sub.367 4-CH.sub.368 2,3-(CH.sub.3).sub.269 2,4-(CH.sub.3).sub.270 2,5-(CH.sub.3).sub.271 2,6-(CH.sub.3).sub.272 3,4-(CH.sub.3).sub.273 3,5-(CH.sub.3).sub.274 3,5-(CH.sub.3).sub.275 2,3,4-(CH.sub.3).sub.376 2,3,6-(CH.sub.3).sub.377 2,4,5-(CH.sub.3).sub.378 2,4,6-(CH.sub.3).sub.379 3,4,5-(CH.sub.3).sub.380 2,3,4,6-(CH.sub.3).sub.481 2,3,5,6-(CH.sub.3).sub.482 2,3,4,5,6-(CH.sub.3).sub.583 2-C.sub.2 H.sub.584 3-C.sub.2 H.sub.585 4-C.sub.2 H.sub.586 2,4-(C.sub.2 H.sub.5).sub.287 2,6-(C.sub.2 H.sub.5).sub.288 3,5-(C.sub.2 H.sub.5).sub.289 2,4,6-(C.sub.2 H.sub.5).sub.390 2-n-C.sub.3 H.sub.791 3-n-C.sub.3 H.sub.792 4-n-C.sub.3 H.sub.793 2-i-C.sub.3 H.sub.794 3-i-C.sub.3 H.sub.795 4-i-C.sub.3 H.sub.796 2,4-(i-C.sub.3 H.sub.7).sub.297 2,6-(i-C.sub.3 H.sub.7).sub.298 3,5-(i-C.sub.3 H.sub.7).sub.299 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub. 3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2C.sub.6 H.sub.5137 3-CH.sub.2C.sub.6 H.sub.5138 4-CH.sub.2C.sub.6 H.sub.5139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub. 3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(i-C.sub.6 H.sub.13)274 3-CHNO(i-C.sub.6 H.sub.13)275 4-CHNO(i-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (i-C.sub.6 H.sub.13)295 3-CO.sub.2 (i-C.sub.6 H.sub.13)296 4-CO.sub.2 (i-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNO CH.sub.2CHCH.sub.2301 3-CHNOCH.sub.2CHCH.sub.2302 4-CHNOCH.sub.2CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 12______________________________________ ##STR39##No. X.sub.m mp NMR: .delta. (ppm)______________________________________1 2-F2 3-F3 4-F4 2,4-F.sub.25 2,4,6-F.sub.36 2,3,4,5,6-F.sub.57 2,3-F.sub.28 2-Cl9 3-Cl10 4-Cl11 2,3-Cl.sub.212 2,4-Cl.sub.213 2,5-Cl.sub.214 2,6-Cl.sub.215 3,4-Cl.sub.216 3,5-Cl.sub.217 2,3,4-Cl.sub.318 2,3,5-Cl.sub.319 2,3,6-Cl.sub.320 2,4,5-Cl.sub.321 2,4,6-Cl.sub.322 3,4,5-Cl.sub.323 2,3,4,6-Cl.sub.424 2,3,5,6-Cl.sub.425 2,3,4,5,6-Cl.sub.526 2-Br27 3-Br28 4-Br29 2,4-Br.sub.230 2,5-Br.sub.531 2,6-Br.sub.232 2,4,6-Br.sub.333 2,3,4,5,6-Br.sub.534 2-I35 3-I36 4-I37 2,4-I.sub.238 2-Cl, 3-F39 2-Cl, 4-F40 2-Cl, 5-F41 2-Cl, 6-F42 2-Cl, 3-Br43 2-Cl, 4-Br44 2-Cl, 6-Br45 2-Cl, 6-Br46 2-Br, 3-Cl47 2-Br, 4-Cl48 2-Br, 5-Cl49 2-Br, 3-F50 2-Br, 4-F51 2-Br, 5-F52 2-Br, 6-F53 2-F, 3-Cl54 2-F, 4-Cl55 2-F, 5-Cl56 3-Cl, 4-F57 3-Cl, 5-F58 3-Cl, 4-Br59 3-Cl, 5-Br60 3-F, 4-Cl61 3-F, 4-Br62 3-Br, 4-Cl63 3-Br, 4-F64 2,6-Cl.sub.2, 4-Br65 2-CH.sub.366 3-CH.sub.367 4-CH.sub.368 2,3-(CH.sub.3).sub.269 2,4-(CH.sub.3).sub.270 2,5-(CH.sub.3).sub.271 2,6-(CH.sub.3).sub.272 3,4-(CH.sub.3).sub.273 3,5-(CH.sub.3).sub.274 3,5-(CH.sub.3).sub.275 2,3,4-(CH.sub.3).sub.376 2,3,6-(CH.sub.3).sub.377 2,4,5-(CH.sub.3).sub.378 2,4,6-(CH.sub.3).sub.379 3,4,5-(CH.sub.3).sub.380 2,3,4,6-(CH.sub.3).sub.481 2,3,5,6-(CH.sub.3).sub.482 2,3,4,5,6-(CH.sub.3).sub.583 2-C.sub.2 H.sub.584 3-C.sub.2 H.sub.585 4-C.sub.2 H.sub.586 2,4-(C.sub.2 H.sub.5).sub.287 2,6-(C.sub.2 H.sub.5).sub.288 3,5-(C.sub.2 H.sub.5).sub.289 2,4,6-(C.sub.2 H.sub.5).sub.390 2-n-C.sub.3 H.sub.791 3-n-C.sub.3 H.sub.792 4-n-C.sub.3 H.sub.793 2-i-C.sub.3 H.sub.794 3-i-C.sub.3 H.sub.795 4-i-C.sub.3 H.sub.796 2,4-(i-C.sub.3 H.sub.7).sub.297 2,6-(i-C.sub.3 H.sub.7).sub.298 3,5-(i-C.sub.3 H.sub.7).sub.299 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub. 3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2C.sub.6 H.sub.5137 3-CH.sub.2C.sub.6 H.sub.5138 4-CH.sub.2C.sub.6 H.sub.5139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub. 3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(i-C.sub.6 H.sub.13)274 3-CHNO(i-C.sub.6 H.sub.13)275 4-CHNO(i-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (i-C.sub.6 H.sub.13)295 3-CO.sub.2 (i-C.sub.6 H.sub.13)296 4-CO.sub.2 (i-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNO CH.sub.2CHCH.sub.2301 3-CHNOCH.sub.2CHCH.sub.2302 4-CHNOCH.sub.2CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 13______________________________________ ##STR40##No. X.sub.m mp NMR: .delta. (ppm)______________________________________1 2-F2 3-F3 4-F4 2,4-F.sub.25 2,4,6-F.sub.36 2,3,4,5,6-F.sub.57 2,3-F.sub.28 2-Cl 83-859 3-Cl oil 5.35(S, 2H); 7.6(S, 1H)10 4-Cl oil 5.35(S, 2H); 7.6(S, 1H)11 2,3-Cl.sub.212 2,4-Cl.sub.213 2,5-Cl.sub.214 2,6-Cl.sub.215 3,4-Cl.sub.216 3,5-Cl.sub.217 2,3,4-Cl.sub.318 2,3,5-Cl.sub.319 2,3,6-Cl.sub.320 2,4,5-Cl.sub.321 2,4,6-Cl.sub.322 3,4,5-Cl.sub.323 2,3,4,6-Cl.sub.424 2,3,5,6-Cl.sub.425 2,3,4,5,6-Cl.sub.526 2-Br27 3-Br28 4-Br29 2,4-Br.sub.230 2,5-Br.sub.531 2,6-Br.sub.232 2,4,6-Br.sub.333 2,3,4,5,6-Br.sub.534 2-I35 3-I36 4-I37 2,4-I.sub.238 2-Cl, 3-F39 2-Cl, 4-F40 2-Cl, 5-F41 2-Cl, 6-F42 2-Cl, 3-Br43 2-Cl, 4-Br44 2-Cl, 6-Br45 2-Cl, 6-Br46 2-Br, 3-Cl47 2-Br, 4-Cl48 2-Br, 5-Cl49 2-Br, 3-F50 2-Br, 4-F51 2-Br, 5-F52 2-Br, 6-F53 2-F, 3-Cl54 2-F, 4-Cl55 2-F, 5-Cl56 3-Cl, 4-F57 3-Cl, 5-F58 3-Cl, 4-Br59 3-Cl, 5-Br60 3-F, 4-Cl61 3-F, 4-Br62 3-Br, 4-Cl63 3-Br, 4-F64 2,6-Cl.sub.2, 4-Br65 2-CH.sub.3 68-6966 3-CH.sub.3 oil 5.35(S, 2H); 7.55(S, 1H)67 4-CH.sub.3 oil 5.35(S, 2H); 7.55(S, 1H)68 2,3-(CH.sub.3).sub.269 2,4-(CH.sub.3).sub.270 2,5-(CH.sub.3).sub.271 2,6-(CH.sub.3).sub.272 3,4-(CH.sub.3).sub.273 3,5-(CH.sub.3).sub.274 3,5-(CH.sub.3).sub.275 2,3,4-(CH.sub.3).sub.376 2,3,6-(CH.sub.3).sub.377 2,4,5-(CH.sub.3).sub.378 2,4,6-(CH.sub.3).sub.379 3,4,5-(CH.sub.3).sub.380 2,3,4,6-(CH.sub.3).sub.481 2,3,5,6-(CH.sub.3).sub.482 2,3,4,5,6-(CH.sub.3).sub.583 2-C.sub.2 H.sub.584 3-C.sub.2 H.sub.585 4-C.sub.2 H.sub.586 2,4-(C.sub.2 H.sub.5).sub.287 2,6-(C.sub.2 H.sub.5).sub.288 3,5-(C.sub.2 H.sub.5).sub.289 2,4,6-(C.sub.2 H.sub.5).sub.390 2-n-C.sub.3 H.sub.791 3-n-C.sub.3 H.sub.792 4-n-C.sub.3 H.sub.793 2-i-C.sub.3 H.sub.794 3-i-C.sub.3 H.sub.795 4-i-C.sub.3 H.sub.796 2,4-(i-C.sub.3 H.sub.7).sub.297 2,6-(i-C.sub.3 H.sub.7).sub.298 3,5-(i-C.sub.3 H.sub.7).sub.299 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub. 3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2C.sub.6 H.sub.5137 3-CH.sub.2C.sub.6 H.sub.5138 4-CH.sub.2C.sub.6 H.sub.5139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3 89-91159 3-OCH.sub.3 72-73160 4-OCH.sub.3 oil 5.35(S, 2H); 7.55(S, 1H)161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7 oil 5.35(S, 2H); 7.55(S, 1H)165 3-O-n-C.sub.3 H.sub.7 oil 5.35(S, 2H); 7.55(S, 1H)166 4-O-n-C.sub.3 H.sub.7 73-74167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13 oil 5.35(S, 2H); 7.55(S, 1H)171 3-O-n-C.sub.6 H.sub.13 43-45172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5 oil 5.35(S, 2H); 7.55(S, 1H)177 3-OCH.sub.2 C.sub.6 H.sub.5 oil 5.35(S, 2H); 7.55(S, 1H)178 4-OCH.sub.2 C.sub.6 H.sub.5 103-106179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5 oil 5.35(S, 2H); 7.55(S, 1H)180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5 oil 5.35(S, 2H); 7.55(S, 1H)181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5 oil 5.35(S, 2H); 7.55(S, 1H)182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 4-CH.sub.3234 2,4-F.sub.2, 4-CH.sub.3235 2,4-Br.sub.2, 4-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(i-C.sub.6 H.sub.13)274 3-CHNO(i-C.sub.6 H.sub.13)275 4-CHNO(i-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (i-C.sub.6 H.sub.13)295 3-CO.sub.2 (i-C.sub.6 H.sub.13)296 4-CO.sub.2 (i-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2CHCH.sub.2301 3-CHNOCH.sub.2CHCH.sub.2302 4-CHNOCH.sub.2CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub. 2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 14______________________________________ ##STR41##No. X.sub.m mp NMR: .delta. (ppm)______________________________________1 2-F2 3-F3 4-F4 2,4-F.sub.25 2,4,6-F.sub.36 2,3,4,5,6-F.sub.57 2,3-F.sub.28 2-Cl9 3-Cl10 4-Cl11 2,3-Cl.sub.212 2,4-Cl.sub.213 2,5-Cl.sub.214 2,6-Cl.sub.215 3,4-Cl.sub.216 3,5-Cl.sub.217 2,3,4-Cl.sub.318 2,3,5-Cl.sub.319 2,3,6-Cl.sub.320 2,4,5-Cl.sub.321 2,4,6-Cl.sub.322 3,4,5-Cl.sub.323 2,3,4,6-Cl.sub.424 2,3,5,6-Cl.sub.425 2,3,4,5,6-Cl.sub.526 2-Br27 3-Br28 4-Br29 2,4-Br.sub.230 2,5-Br.sub.531 2,6-Br.sub.232 2,4,6-Br.sub.333 2,3,4,5,6-Br.sub.534 2-I35 3-I36 4-I37 2,4-I.sub.238 2-Cl, 3-F39 2-Cl, 4-F40 2-Cl, 5-F41 2-Cl, 6-F42 2-Cl, 3-Br43 2-Cl, 4-Br44 2-Cl, 6-Br45 2-Cl, 6-Br46 2-Br, 3-Cl47 2-Br, 4-Cl48 2-Br, 5-Cl49 2-Br, 3-F50 2-Br, 4-F51 2-Br, 5-F52 2-Br, 6-F53 2-F, 3-Cl54 2-F, 4-Cl55 2-F, 5-Cl56 3-Cl, 4-F57 3-Cl, 5-F58 3-Cl, 4-Br59 3-Cl, 5-Br60 3-F, 4-Cl61 3-F, 4-Br62 3-Br, 4-Cl63 3-Br, 4-F64 2,6-Cl.sub.2, 4-Br65 2-CH.sub.366a) 3-CH.sub.3 : non-polar isomer oil 3.9(S, 3H); 4.0(S, 3H); 5.15(S, 2H)66b) 3-CH.sub.3 : polar isomer 66-7067 4-CH.sub.368 2,3-(CH.sub.3).sub.269 2,4-(CH.sub.3).sub.270 2,5-(CH.sub.3).sub.271 2,6-(CH.sub.3).sub.272 3,4-(CH.sub.3).sub.273 3,5-(CH.sub.3).sub.274 3,5-(CH.sub.3).sub.275 2,3,4-(CH.sub.3).sub.376 2,3,6-(CH.sub.3).sub.377 2,4,5-(CH.sub.3).sub.378 2,4,6-(CH.sub.3).sub.379 3,4,5-(CH.sub.3).sub.380 2,3,4,6-(CH.sub.3).sub.481 2,3,5,6-(CH.sub.3).sub.482 2,3,4,5,6-(CH.sub.3).sub.583 2-C.sub.2 H.sub.584 3-C.sub.2 H.sub.585 4-C.sub.2 H.sub.586 2,4-(C.sub.2 H.sub.5).sub.287 2,6-(C.sub.2 H.sub.5).sub.288 3,5-(C.sub.2 H.sub.5).sub.289 2,4,6-(C.sub.2 H.sub.5).sub.390 2-n-C.sub.3 H.sub.791 3-n-C.sub.3 H.sub.792 4-n-C.sub.3 H.sub.793 2-i-C.sub.3 H.sub.794 3-i-C.sub.3 H.sub.795 4-i-C.sub.3 H.sub.796 2,4-(i-C.sub.3 H.sub.7).sub.297 2,6-(i-C.sub.3 H.sub.7).sub.298 3,5-(i-C.sub.3 H.sub.7).sub.299 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-SC.sub.4 H.sub.9101 3-SC.sub.4 H.sub.9102 4-SC.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub. 3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2C.sub.6 H.sub.5137 3-CH.sub.2C.sub.6 H.sub.5138 4-CH.sub.2C.sub.2 H.sub.5139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-OC.sub.2 H.sub.5163 4-OC.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-OCH.sub.2 C.sub.6 H.sub.5177 3-OCH.sub.2 C.sub.6 H.sub.5178 4-OCH.sub.2 C.sub.6 H.sub.5179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub. 2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub.3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub. 5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2CHCH.sub.2301 3-CHNOCH.sub.2CHCH.sub.2302 4-CHNOCH.sub.2CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub. 17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 15______________________________________ ##STR42##No. X.sub.m mp NMR: .delta. (ppm)______________________________________ 1 2-F 2 3-F 3 4-F 4 2,4-F.sub.2 5 2,4,6-F.sub.3 6 2,3,4,5,6-F.sub.5 7 2,3-F.sub.2 8 2-Cl 9 3-Cl 10 4-Cl 11 2,3-Cl.sub.2 12 2,4-Cl.sub.2 13 2,5-Cl.sub.2 14 2,6-Cl.sub.2 15 3,4-Cl.sub.2 16 3,5-Cl.sub.2 17 2,3,4-Cl.sub.3 18 2,3,5-Cl.sub.3 19 2,3,6-Cl.sub.3 20 2,4,5-Cl.sub.3 21 2,4,6-Cl.sub.3 22 3,4,5-Cl.sub.3 23 2,3,4,6-Cl.sub.4 24 2,3,5,6-Cl.sub.4 25 2,3,4,5,6-Cl.sub.5 26 2-Br 27 3-Br 28 4-Br 29 2,4-Br.sub.2 30 2,5-Br.sub.5 31 2,6-Br.sub.2 32 2,4,6-Br.sub.3 33 2,3,4,5,6-Br.sub.5 34 2-I 35 3-I 36 4-I 37 2,4-I.sub.2 38 2-Cl, 3-F 39 2-Cl, 4-F 40 2-Cl, 5-F 41 2-Cl, 6-F 42 2-Cl, 3-Br 43 2-Cl, 4-Br 44 2-Cl, 6-Br 45 2-Cl, 6-Br 46 2-Br, 3-Cl 47 2-Br, 4-Cl 48 2-Br, 5-Cl 49 2-Br, 3-F 50 2-Br, 4-F 51 2-Br, 5-F 52 2-Br, 6-F 53 2-F, 3-Cl 54 2-F, 4-Cl 55 2-F, 5-Cl 56 3-Cl, 4-F 57 3-Cl, 5-F 58 3-Cl, 4-Br 59 3-Cl, 5-Br 60 3-F, 4-Cl 61 3-F, 4-Br 62 3-Br, 4-Cl 63 3-Br, 4-F 64 2,6-Cl.sub.2, 4-Br 65 2-CH.sub.3 66 3-CH.sub.3 67 4-CH.sub.3 68 2,3-(CH.sub.3).sub.2 69 2,4-(CH.sub.3).sub.2 70 2,5-(CH.sub.3).sub.2 71 2,6-(CH.sub.3).sub.2 72 3,4-(CH.sub.3).sub.2 73 3,5-(CH.sub.3).sub.2 74 3,5-(CH.sub.3).sub.2 75 2,3,4-(CH.sub.3).sub.3 76 2,3,6-(CH.sub.3).sub.3 77 2,4,5-(CH.sub.3).sub.3 78 2,4,6-(CH.sub.3).sub.3 79 3,4,5-(CH.sub.3).sub.3 80 2,3,4,6-(CH.sub.3).sub.4 81 2,3,5,6-(CH.sub.3).sub.4 82 2,3,4,5,6-(CH.sub.3).sub.5 83 2-C.sub.2 H.sub.5 84 3-C.sub.2 H.sub.5 85 4-C.sub.2 H.sub.5 86 2,4-(C.sub.2 H.sub.5).sub.2 87 2,6-(C.sub.2 H.sub.5).sub.2 88 3,5-(C.sub.2 H.sub.5).sub.2 89 2,4,6-(C.sub.2 H.sub.5).sub.3 90 2-n-C.sub.3 H.sub.7 91 3-n-C.sub.3 H.sub.7 92 4-n-C.sub.3 H.sub.7 93 2-i-C.sub.3 H.sub.7 94 3-i-C.sub.3 H.sub.7 95 4-i-C.sub.3 H.sub.7 96 2,4-(i-C.sub.3 H.sub.7).sub.2 97 2,6-(i-C.sub.3 H.sub.7).sub.2 98 3,5-(i-C.sub.3 H.sub.7).sub.2 99 2,4,6-(i-C.sub.3 H.sub.7).sub.3100 2-S-C.sub.4 H.sub.9101 3-S-C.sub.4 H.sub.9102 4-S-C.sub.4 H.sub.9103 2-t-C.sub.4 H.sub.9104 3-t-C.sub.4 H.sub.9105 4-t-C.sub.4 H.sub.9106 2,3-(t-C.sub.4 H.sub.9).sub.2107 2,4-(t-C.sub.4 H.sub.9).sub.2108 2,5-(t-C.sub.4 H.sub.9).sub.2109 2,6-(t-C.sub.4 H.sub.9).sub.2110 3,4-(t-C.sub.4 H.sub.9).sub.2111 2,4,6-(t-C.sub.4 H.sub.9).sub.3112 4-n-C.sub.9 H.sub.19113 4-n-C.sub.12 H.sub.25114 3-n-C.sub.15 H.sub.31115 4-(1,1,3,3-tetramethylbutyl)116 4-(2,4,4-trimethylpropyl117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7127 2-allyl128 3-allyl129 4-allyl130 2-allyl, 6-CH.sub.3131 2-cyclo-C.sub.6 H.sub.11132 3-cyclo-C.sub.6 H.sub.11133 4-cyclo-C.sub.6 H.sub.11134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11136 2-CH.sub.2 C.sub.6 H.sub.5137 3-CH.sub.2 C.sub.6 H.sub.5138 4-CH.sub.2 C.sub.2 H.sub.5139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5141 2-C.sub.6 H.sub.5142 3-C.sub.6 H.sub.5143 4-C.sub.6 H.sub.5144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2146 2-Cl, 4-C.sub.6 H.sub.5147 2-Br, 4-C.sub.6 H.sub.5148 2-C.sub.6 H.sub.5, 4-Cl149 2-C.sub.6 H.sub.5, 4-Br150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5154 2-cyclo-C.sub.6 H.sub.11, 4-Cl155 2-cyclo-C.sub.6 H.sub.11, 4-Br156 2-Cl, 4-cyclo-C.sub.6 H.sub.11157 2-Br, 4-cyclo-C.sub.6 H.sub.11158 2-OCH.sub.3159 3-OCH.sub.3160 4-OCH.sub.3161 2-OC.sub.2 H.sub.5162 3-O-C.sub.2 H.sub.5163 4-O-C.sub.2 H.sub.5164 2-O-n-C.sub.3 H.sub.7165 3-O-n-C.sub.3 H.sub.7166 4-O-n-C.sub.3 H.sub.7167 2-O-i-C.sub.3 H.sub.7168 3-O-i-C.sub.3 H.sub.7169 4-O-i-C.sub.3 H.sub.7170 2-O-n-C.sub.6 H.sub.13171 3-O-n-C.sub.6 H.sub.13172 4-O-n-C.sub.6 H.sub.13173 2-O-n-C.sub.8 H.sub.17174 3-O-n-C.sub.8 H.sub.17175 4-O-n-C.sub.8 H.sub.17176 2-O-CH.sub.2 C.sub.6 H.sub.5177 3-O-CH.sub. 2 C.sub.6 H.sub.5178 4-O-CH.sub.2 C.sub.6 H.sub.5179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5182 2,4-(OCH.sub.3).sub.2183 2-CF.sub.3184 3-CF.sub.3185 4-CF.sub.3186 2-OCF.sub.3187 3-OCF.sub.3188 4-OCF.sub.3189 3-OCH.sub.2 CHF.sub.2190 2-NO.sub.2191 3-NO.sub.2192 4-NO.sub.2193 2-CN194 3-CN195 4-CN196 2-CH.sub.3, 3-Cl197 2-CH.sub.3, 4-Cl198 2-CH.sub.3, 5-Cl199 2-CH.sub.3, 6-Cl200 2-CH.sub.3, 3-F201 2-CH.sub.3, 4-F202 2-CH.sub.3, 5-F203 2-CH.sub.3, 6-F204 2-CH.sub.3, 3-Br205 2-CH.sub.3, 4-Br206 2-CH.sub.3, 5-Br207 2-CH.sub.3, 6-Br208 2-Cl, 3-CH.sub.3209 2-Cl, 4-CH.sub.3210 2-Cl, 5-CH.sub.3211 2-F, 3-CH.sub.3212 2-F, 4-CH.sub.3213 2-F, 5-CH.sub.3214 2-Br, 3-CH.sub.3215 2-Br, 4-CH.sub.3216 2-Br, 5-CH.sub.3217 3-CH.sub.3, 4-Cl218 3-CH.sub.3, 5-Cl219 3-CH.sub.3, 4-F220 3-CH.sub.3, 4-Br221 3-CH.sub. 3, 4-Br222 3-CH.sub.3, 5-Br223 3-F, 4-CH.sub.3224 3-Cl, 4-CH.sub.3225 3-Br, 4-CH.sub.3226 2-Cl, 4,5-(CH.sub.3).sub.2227 2-Br, 4,5-(CH.sub.3).sub.2228 2-Cl, 3,5-(CH.sub.3).sub.2229 2-Br, 3,5-(CH.sub.3).sub.2230 2,6-Cl.sub.2, 4-CH.sub.3231 2,6-F.sub.2, 4-CH.sub.3232 2,6-Br.sub.2, 4-CH.sub.3233 2,4-Cl.sub.2, 6-CH.sub.3234 2,4-F.sub.2, 6-CH.sub.3235 2,4-Br.sub.2, 6-CH.sub.3236 2,6-(CH.sub.3).sub.2, 4-F237 2,6-(CH.sub.3).sub.2, 4-Cl238 2,6-(CH.sub.3).sub.2, 4-Br239 3,5-(CH.sub.3).sub.2, 4-F240 3,5-(CH.sub.3).sub.2, 4-Cl241 3,5-(CH.sub.3).sub.2, 4-Br242 2,3,6-(CH.sub.3).sub.3, 4-F243 2,3,6-(CH.sub.3).sub.3, 4-Cl244 2,3,6-(CH.sub.3).sub.3, 4-Br245 2,4-(CH.sub.3).sub.2, 6-F246 2,4-(CH.sub.3).sub.2, 6-Cl247 2,4-(CH.sub.3).sub.62, 6-Br248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3249 2-Cl, 4-NO.sub.2250 2-NO.sub.2, 4-Cl251 2-OCH.sub.3, 5-NO.sub.2252 2,4-Cl.sub.2, 5-NO.sub.2253 2,4-Cl.sub.2, 6-NO.sub.2254 2,6-Cl.sub.2, 4-NO.sub.2255 2,6-Br.sub.2, 4-NO.sub.2256 2,6-I.sub.2, 4-NO.sub.2257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl258 2-C.sub.6 H.sub.5 O259 3-C.sub.6 H.sub.5 O260 4-C.sub.6 H.sub.5 O261 2-CHNOCH.sub.3262 3-CHNOCH.sub.3263 4-CHNOCH.sub.3264 2-CHNOC.sub.2 H.sub.5265 3-CHNOC.sub.2 H.sub.5266 4-CHNOC.sub.2 H.sub.5267 2-CHNO(n-C.sub.3 H.sub.7)268 3-CHNO(n-C.sub.3 H.sub.7)269 4-CHNO(n-C.sub.3 H.sub.7)270 2-CHNO(i-C.sub.3 H.sub.7)271 3-CHNO(i-C.sub.3 H.sub.7)272 4-CHNO(i-C.sub.3 H.sub.7)273 2-CHNO(n-C.sub.6 H.sub.13)274 3-CHNO(n-C.sub.6 H.sub.13)275 4-CHNO(n-C.sub.6 H.sub.13)276 2-CHNO(n-C.sub.8 H.sub.17)277 3-CHNO(n-C.sub.8 H.sub.17)278 4-CHNO(n-C.sub.8 H.sub.17)279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)282 2-CO.sub.2 CH.sub.3283 3-CO.sub.2 CH.sub.3284 4-CO.sub.2 CH.sub.3285 2-CO.sub.2 (C.sub.2 H.sub.5)286 3-CO.sub.2 (C.sub.2 H.sub.5)287 4-CO.sub.2 (C.sub.2 H.sub.5)288 2-CO.sub.2 (n-C.sub.3 H.sub.7)289 3-CO.sub.2 (n-C.sub.3 H.sub.7)290 4-CO.sub.2 (n-C.sub.3 H.sub.7)291 2-CO.sub.2 (i-C.sub.3 H.sub.7)292 3-CO.sub.2 (i-C.sub.3 H.sub.7)293 4-CO.sub.2 (i-C.sub.3 H.sub.7)294 2-CO.sub.2 (n-C.sub.6 H.sub.13)295 3-CO.sub.2 (n-C.sub.6 H.sub.13)296 4-CO.sub.2 (n-C.sub.6 H.sub.13)297 2-CO.sub.2 (n-C.sub.8 H.sub.17)298 3-CO.sub.2 (n-C.sub.8 H.sub.17)299 4-CO.sub.2 (n-C.sub.8 H.sub.17)300 2-CHNOCH.sub.2 CHCH.sub.2301 3-CHNOCH.sub.2 CHCH.sub.2302 4-CHNOCH.sub.2 CHCH.sub.2303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)306 2-CH.sub.2 OCH.sub.3307 3-CH.sub.2 OCH.sub.3308 4-CH.sub.2 OCH.sub.3309 2-CH.sub.2 O(C.sub.2 H.sub.5)310 3-CH.sub.2 O(C.sub.2 H.sub.5)311 4-CH.sub.2 O(C.sub.2 H.sub.5)312 2-CH.sub.2 O(n-C.sub.3 H.sub. 7)313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)327 2-CH.sub.2 O(CH.sub.2).sub.3328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)330 2-CHO331 3-CHO332 4-CHO______________________________________
TABLE 16______________________________________ ##STR43##No. Aryl mp NMR: .delta. (ppm)______________________________________ 1 1-naphthyl 2 2-naphthyl 3 3-phenanthrenyl 4 2-chlorophenyl 5 2-bromophenyl 6 3-bromophenyl 7 4-bromophenyl 8 2-fluorophenyl 9 3-fluorophenyl10 4-fluorophenyl11 2-ethyl-phenyl12 3-ethyl-phenyl13 4-ethyl-phenyl14 2-iso-propyl-phenyl15 3-iso-propyl-phenyl16 4-iso-propyl-phenyl17 2-tert-butyl-phenyl18 3-tert-butyl-phenyl19 4-tert-butyl-phenyl20 4-butyl-phenyl21 4-hexyl-phenyl22 4-nonyl-phenyl23 4-decyl-phenyl24 2-methoxy-phenyl25 3-methoxy-phenyl26 4-methoxy-phenyl27 2-trifluoromethyl-phenyl28 3-trifluoromethyl-phenyl29 4-trifluoromethyl-phenyl30 4-formyl-phenyl31 2-nitro-phenyl32 3-nitro-phenyl33 4-nitro-phenyl34 2,5-dichlorophenyl35 2,6-dichlorophenyl36 3,4-dichlorophenyl37 2,3-dichlorophenyl38 3,5-dichlorophenyl39 2,3,4-trichlorophenyl40 2,4,5-trichlorophenyl41 2,4,6-trichlorophenyl42 2,3,4,6-tetrachlorophenyl43 2,3,4,5,6-pentachlorophenyl44 2,3,4,5-tetrafluorophenyl45 2,3,5,6-tetrafluorophenyl46 2,3,4,5,6-pentafluorophenyl47 2-chloro, 4-fluorophenyl48 3-chloro, 4-fluorophenyl49 2-chloro, 6-methyl-phenyl50 4-chloro, 2-methyl-phenyl51 2,4-dichloro, 5-methyl-phenyl52 4-chloro, 2,5-dimethyl-phenyl53 3-bromo, 3-methyl-phenyl54 3,5-bistrifluoromethyl-phenyl55 2,5-dimethyl-phenyl56 2,4-dimethyl-phenyl57 2,5-dimethyl-phenyl58 2,6-dimethyl-phenyl59 3,4-dimethyl-phenyl60 3,5-dimethyl-phenyl61 2,4,5-trimethyl-phenyl62 2,6-diethyl-phenyl63 2,4-di-tert.-butyl-phenyl64 2,5-dimethoxy-phenyl65 3,4-dimethoxy-phenyl66 2-methyl, 4-tert.-butyl-phenyl67 2-methoxycarbonyl-phenyl68 2-ethoxycarbonyl-phenyl69 2-propoxycarbonyl-phenyl70 2-butoxycarbonyl-phenyl71 2-cyano-phenyl72 3-cyano-phenyl73 4-cyano-phenyl______________________________________
TABLE 17______________________________________ ##STR44##No. Aryl mp NMR: .delta. (ppm)______________________________________ 1 1-naphthyl 2 2-naphthyl 3 3-phenanthrenyl 4 2-chlorophenyl 5 2-bromophenyl 6 3-bromophenyl 7 4-bromophenyl 8 2-fluorophenyl 9 3-fluorophenyl10 4-fluorophenyl11 2-ethyl-phenyl12 3-ethyl-phenyl13 4-ethyl-phenyl14 2-iso-propyl-phenyl15 3-iso-propyl-phenyl16 4-iso-propyl-phenyl17 2-tert-butyl-phenyl18 3-tert-butyl-phenyl19 4-tert-butyl-phenyl20 4-butyl-phenyl21 4-hexyl-phenyl22 4-nonyl-phenyl23 4-decyl-phenyl24 2-methoxy-phenyl25 3-methoxy-phenyl26 4-methoxy-phenyl27 2-trifluoromethyl-phenyl28 3-trifluoromethyl-phenyl29 4-trifluoromethyl-phenyl30 4-formyl-phenyl31 2-nitro-phenyl32 3-nitro-phenyl33 4-nitro-phenyl34 2,5-dichlorophenyl35 2,6-dichlorophenyl36 3,4-dichlorophenyl37 2,3-dichlorophenyl38 3,5-dichlorophenyl39 2,3,4-trichlorophenyl40 2,4,5-trichlorophenyl41 2,4,6-trichlorophenyl42 2,3,4,6-tetrachlorophenyl43 2,3,4,5,6-pentachlorophenyl44 2,3,4,5-tetrafluorophenyl45 2,3,5,6-tetrafluorophenyl46 2,3,4,5,6-pentafluorophenyl47 2-chloro, 4-fluorophenyl48 3-chloro, 4-fluorophenyl49 2-chloro, 6-methyl-phenyl50 4-chloro, 2-methyl-phenyl51 2,4-dichloro, 5-methyl-phenyl52 4-chloro, 2,5-dimethyl-phenyl53 3-bromo, 3-methyl-phenyl54 3,5-bistrifluoromethyl-phenyl55 2,5-dimethyl-phenyl56 2,4-dimethyl-phenyl57 2,5-dimethyl-phenyl58 2,6-dimethyl-phenyl59 3,4-dimethyl-phenyl60 3,5-dimethyl-phenyl61 2,4,5-trimethyl-phenyl62 2,6-diethyl-phenyl63 2,4-di-tert.-butyl-phenyl64 2,5-dimethoxy-phenyl65 3,4-dimethoxy-phenyl66 2-methyl, 4-tert.-butyl-phenyl67 2-methoxycarbonyl-phenyl68 2-ethoxycarbonyl-phenyl69 2-propoxycarbonyl-phenyl70 2-butoxycarbonyl-phenyl71 2-cyano-phenyl72 3-cyano-phenyl73 4-cyano-phenyl______________________________________
TABLE 18______________________________________ ##STR45##No. Aryl mp NMR: .delta. (ppm)______________________________________ 1 1-naphthyl 2 2-naphthyl 3 3-phenanthrenyl 4 2-chlorophenyl 5 2-bromophenyl 6 3-bromophenyl 7 4-bromophenyl 8 2-fluorophenyl 9 3-fluorophenyl10 4-fluorophenyl11 2-ethyl-phenyl12 3-ethyl-phenyl13 4-ethyl-phenyl14 2-iso-propyl-phenyl15 3-iso-propyl-phenyl16 4-iso-propyl-phenyl17 2-tert-butyl-phenyl18 3-tert-butyl-phenyl19 4-tert-butyl-phenyl20 4-butyl-phenyl21 4-hexyl-phenyl22 4-nonyl-phenyl23 4-decyl-phenyl24 2-methoxy-phenyl25 3-methoxy-phenyl26 4-methoxy-phenyl27 2-trifluoromethyl-phenyl28 3-trifluoromethyl-phenyl29 4-trifluoromethyl-phenyl30 4-formyl-phenyl31 2-nitro-phenyl32 3-nitro-phenyl33 4-nitro-phenyl34 2,5-dichlorophenyl35 2,6-dichlorophenyl36 3,4-dichlorophenyl37 2,3-dichlorophenyl38 3,5-dichlorophenyl39 2,3,4-trichlorophenyl40 2,4,5-trichlorophenyl41 2,4,6-trichlorophenyl42 2,3,4,6-tetrachlorophenyl43 2,3,4,5,6-pentachlorophenyl44 2,3,4,5-tetrafluorophenyl45 2,3,5,6-tetrafluorophenyl46 2,3,4,5,6-pentafluorophenyl47 2-chloro, 4-fluorophenyl48 3-chloro, 4-fluorophenyl49 2-chloro, 6-methyl-phenyl50 4-chloro, 2-methyl-phenyl51 2,4-dichloro, 5-methyl-phenyl52 4-chloro, 2,5-dimethyl-phenyl53 3-bromo, 3-methyl-phenyl54 3,5-bistrifluoromethyl-phenyl55 2,5-dimethyl-phenyl56 2,4-dimethyl-phenyl57 2,5-dimethyl-phenyl58 2,6-dimethyl-phenyl59 3,4-dimethyl-phenyl60 3,5-dimethyl-phenyl61 2,4,5-trimethyl-phenyl62 2,6-diethyl-phenyl63 2,4-di-tert.-butyl-phenyl64 2,5-dimethoxy-phenyl65 3,4-dimethoxy-phenyl66 2-methyl, 4-tert.-butyl-phenyl67 2-methoxycarbonyl-phenyl68 2-ethoxycarbonyl-phenyl69 2-propoxycarbonyl-phenyl70 2-butoxycarbonyl-phenyl71 2-cyano-phenyl72 3-cyano-phenyl73 4-cyano-phenyl______________________________________
TABLE 19__________________________________________________________________________ ##STR46##No. A Hetaryl mp NMR: .delta. (ppm)__________________________________________________________________________ 1 CH.sub.2 S 4-pyridyl 76-77 2 CH.sub.2 O 6-methyl-2-pyridyl 76-77 3 CH.sub.2 S 6-methyl-2-pyridyl 4 CH.sub.2 O 6-ethyl-2-pyridyl 5 CH.sub.2 S 6-ethyl-2-pyridyl 6 CH.sub.2 O 6-n-propyl-2-pyridyl 7 CH.sub.2 S 6-n-propyl-2-pyridyl 8 CH.sub.2 O 6-iso-propyl-2-pyridyl 9 CH.sub.2 S 6-iso-propyl-2-pyridyl 10 CH.sub.2 O 6-n-butyl-2-pyridyl 11 CH.sub.2 S 6-n-butyl-2-pyridyl 12 CH.sub.2 O 6-tert.-butyl-2-pyridyl 13 CH.sub.2 S 6-tert.-butyl-2-pyridyl 14 CH.sub.2 O 6-n-pentyl-2-pyridyl 15 CH.sub.2 S 6-n-pentyl-2-pyridyl 16 CH.sub.2 O 6-n-hexyl-2-pyridyl 17 CH.sub.2 S 6-n-hexyl-2-pyridyl 18 CH.sub.2 O 6-phenyl-2-pyridyl 19 CH.sub.2 S 6-phenyl-2-pyridyl 20 CH.sub.2 O 6-benzyl-2-pyridyl 21 CH.sub.2 S 6-benzyl-2-pyridyl 22 CH.sub.2 S 6-benzyl-2-pyridyl 23 CH.sub.2 S 6-trifluoromethyl-2-pyridyl 24 CH.sub.2 O 6-methoxy-2-pyridyl 25 CH.sub.2 S 6-methoxy-2-pyridyl 26 CH.sub.2 O 6-chloro-2-pyridyl 72-73 27 CH.sub.2 S 6-chloro-2-pyridyl 28 CH.sub.2 O 3,6-dimethyl-2-pyridyl 29 CH.sub.2 S 3,6-dimethyl-2-pyridyl 30 CH.sub.2 O 3,6-diethyl-2-pyridyl 31 CH.sub.2 S 3,6-diethyl-2-pyridyl 32 CH.sub.2 O 4,6-dimethyl-2-pyridyl 33 CH.sub.2 S 4,6-dimethyl-2-pyridyl 34 CH.sub.2 O 5,6-dimethyl-2-pyridyl 35 CH.sub.2 S 5,6-dimethyl-2-pyridyl 36 CH.sub.2 O 4-phenyl-6-methyl-2-pyridyl 37 CH.sub.2 S 4-phenyl-6-methyl-2-pyridyl 38 CH.sub.2 O 4,6-diphenyl-2-pyridyl 39 CH.sub.2 S 4,6-diphenyl-2-pyridyl 40 CH.sub.2 O 3,4-dichloro-6-methyl-2-pyridyl 41 CH.sub.2 S 3,4-dichloro-6-methyl-2-pyridyl 42 CH.sub.2 O 3,4,5-trichloro-6-phenyl-2-pyridyl 43 CH.sub.2 S 3,4,5-trichloro-6-phenyl-2-pyridyl 44 CH.sub.2 O 4-trifluoromethyl-6-methyl-2-pyridyl 45 CH.sub.2 S 4-trifluoromethyl-6-methyl-2-pyridyl 46 CH.sub.2 O 3-acetyl-4,6-dimethyl-2-pyridyl 47 CH.sub.2 S 3-acetyl-4,6-dimethyl-2-pyridyl 48 CH.sub.2 O 3-cyano-6-methyl-2-pyridyl 49 CH.sub.2 S 3-cyano-6-methyl-2-pyridyl 50 CH.sub. 2 O 3-cyano-6-ethyl-2-pyridyl 51 CH.sub.2 S 3-cyano-6-ethyl-2-pyridyl 52 CH.sub.2 O 3-cyano-6-n-propyl-2-pyridyl 53 CH.sub.2 S 3-cyano-6-n-propyl-2-pyridyl 54 CH.sub.2 O 3-cyano-6-iso-propyl-2-pyridyl 55 CH.sub.2 S 3-cyano-6-iso-propyl-2-pyridyl 56 CH.sub.2 O 3-cyano-6-cyclo-propyl-2-pyridyl 57 CH.sub.2 S 3-cyano-6-cyclo-propyl-2-pyridyl 58 CH.sub.2 O 3-cyano-6-n-butyl-2-pyridyl 59 CH.sub.2 S 3-cyano-6-n-butyl-2-pyridyl 60 CH.sub.2 O 3-cyano-6-tert.-butyl-2-pyridyl 61 CH.sub.2 S 3-cyano-6-tert.-butyl-2-pyridyl 62 CH.sub.2 O 3-cyano-6-cyclo-hexyl-2-pyridyl 63 CH.sub.2 S 3-cyano-6-cyclo-hexyl-2-pyridyl 64 CH.sub.2 O 3-cyano-6-phenyl-2-pyridyl 65 CH.sub.2 S 3-cyano-6-phenyl-2-pyridyl 66 CH.sub.2 O 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl 67 CH.sub.2 S 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl 68 CH.sub.2 O 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl 69 CH.sub.2 S 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl 70 CH.sub.2 O 3-cyano-4,6-dimethyl-2-pyridyl 71 CH.sub.2 S 3-cyano-4,6-dimethyl-2-pyridyl 72 CH.sub.2 O 3,5,6-trichloro-2-pyridyl 73 CH.sub.2 S 3,5,6-trichloro-2-pyridyl 74 CH.sub.2 O 5-trifluoromethyl-2-pyridyl 75 CH.sub.2 S 5-trifluoromethyl-2-pyridyl 76 CH.sub.2 O 3-chloro-5-trifluoromethyl-2-pyridyl 77 CH.sub.2 S 3-chloro-5-trifluoromethyl-2-pyridyl 78 CH.sub.2 O 2-quinolyl 79 CH.sub.2 S 2-quinolyl 80 CH.sub.2 O 3-methyl-2-quinolyl 81 CH.sub.2 S 3-methyl-2-quinolyl 82 CH.sub.2 O 4-methyl-2-quinolyl 83 CH.sub.2 S 4-methyl-2-quinolyl 84 CH.sub.2 O 4-ethyl-2-quinolyl 85 CH.sub.2 S 4-ethyl-2-quinolyl 86 CH.sub.2 O 4-phenyl-2-quinolyl 87 CH.sub.2 S 4-phenyl-2-quinolyl 88 CH.sub.2 O 6-methyl-2-quinolyl 89 CH.sub.2 S 6-methyl-2-quinolyl 90 CH.sub.2 O 6-chloro-2-quinolyl 91 Ch.sub.2 S 6-chloro-2-quinolyl 92 CH.sub.2 O 8-methyl-2-quinolyl 93 CH.sub.2 S 8-methyl-2-quinolyl 94 CH.sub.2 O 8-chloro-2-quinolyl 95 CH.sub.2 S 8-chloro-2-quinolyl 96 CH.sub.2 O 4-Ethoxycarbonyl-2-quinolyl 97 CH.sub.2 S 4-Ethoxycarbonyl-2-quinolyl 98 CH.sub.2 O 3,4-dimethyl-2-quinolyl 99 CH.sub.2 S 3,4-dimethyl-2-quinolyl100 CH.sub.2 O 4-methyl-8-methoxy-2-quinolyl101 CH.sub.2 S 4-methyl-8-methoxy-2-quinolyl102 CH.sub.2 O 4-phenyl-8-ethoxy-2-quinolyl103 CH.sub.2 S 4-phenyl-8-ethoxy-2-quinolyl104 CH.sub.2 O 4-methyl-8-chloro-2-quinolyl105 CH.sub.2 S 4-methyl-8-chloro-2-quinolyl106 CH.sub.2 O 4-methyl-8-fluoro-2-quinolyl107 CH.sub.2 S 4-methyl-8-fluoro-2-quinolyl108 CH.sub.2 O 4-quinolyl109 CH.sub.2 S 4-quinolyl110 CH.sub.2 O 2-methyl-4-quinolyl111 CH.sub.2 S 2-methyl-4-quinolyl112 CH.sub.2 O 2-trichloromethyl-4-quinolyl113 CH.sub.2 S 2-trichloromethyl-4-quinolyl114 CH.sub.2 O 2-trifluoromethyl-2-quinolyl115 CH.sub.2 S 2-trifluoromethyl-2-quinolyl116 CH.sub.2 O 2-iso-propyl-4-quinolyl117 CH.sub.2 S 2-iso-propyl-4-quinolyl118 CH.sub.2 O 2-n-pentyl-4-quinolyl119 CH.sub.2 S 2-n-pentyl-4-quinolyl120 CH.sub.2 O 2-phenyl-4-quinolyl121 CH.sub.2 S 2-phenyl-4-quinolyl122 CH.sub.2 O 2-methoxycarbonyl-4-quinolyl123 CH.sub.2 S 2-methoxycarbonyl-4-quinolyl124 CH.sub.2 O 2,6-dimethyl-4-quinolyl125 CH.sub.2 S 2,6-dimethyl-4-quinolyl126 CH.sub.2 O 2-methyl-6-chloro-4-quinolyl127 CH.sub.2 S 2-methyl-6-chloro-4-quinolyl128 CH.sub.2 O 2-methyl-6-fluoro-4-quinolyl129 CH.sub.2 S 2-methyl-6-fluoro-4-quinolyl130 CH.sub.2 O 8-quinolyl131 CH.sub.2 S 8-quinolyl132 CH.sub.2 O 2-methyl-8-quinolyl133 CH.sub.2 S 2-methyl-8-quinolyl134 CH.sub.2 O 5,7-dichloro-8-quinolyl135 CH.sub.2 S 5,7-dichloro-8-quinolyl136 CH.sub.2 O 4,6-dimethyl-2-pyrimidinyl137 CH.sub.2 S 4,6-dimethyl-2-pyrimidinyl138 CH.sub.2 O 4-trifluoromethyl-2-pyrimidinyl139 CH.sub.2 S 4-trifluoromethyl-2-pyrimidinyl140 CH.sub.2 O 4,5,6-trimethyl-2-pyrimidinyl141 CH.sub.2 S 4,5,6-trimethyl-2-pyrimidinyl142 CH.sub.2 O 4-benzyl-6-methyl-2-pyrimidinyl143 CH.sub.2 S 4-benzyl-6-methyl-2-pyrimidinyl144 CH.sub.2 O 4-methyl-6-phenyl-2-pyrimidinyl145 CH.sub.2 S 4-methyl-6-phenyl-2-pyrimidinyl146 CH.sub.2 O 4,6-dimethyl-5-chloro-2-pyrimidinyl147 CH.sub.2 S 4,6-dimethyl-5-chloro-2-pyrimidinyl148 CH.sub.2 O 2,6-dimethyl-4-pyrimidinyl149 CH.sub.2 S 2,6-dimethyl-4-pyrimidinyl150 CH.sub.2 O 2,6-bis-(trifluoromethyl)-4-pyrimidinyl151 CH.sub.2 S 2,6-bis-(trifluoromethyl)-4-pyrimidinyl152 CH.sub.2 O 2-chloromethyl-6-methyl-4-pyrimidinyl153 CH.sub.2 S 2-chloromethyl-6-methyl-4-pyrimidinyl154 CH.sub.2 O 2-methyl-6-chloromethyl-4-pyrimidinyl155 CH.sub.2 S 2-methyl-6-chloromethyl-4-pyrimidinyl156 CH.sub.2 O 2-iso-propyl-6-methyl-4-pyrimidinyl157 CH.sub.2 S 2-iso-propyl-6-methyl-4-pyrimidinyl158 CH.sub.2 O 2-iso-propyl-6-chloromethyl-4-pyrimidinyl159 CH.sub.2 S 2-iso-propyl-6-chloromethyl-4-pyrimidinyl160 CH.sub.2 O 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl161 CH.sub.2 S 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl162 CH.sub.2 O 2-cyclo-propyl-6-methyl-4-pyrimidinyl163 CH.sub.2 S 2-cyclo-propyl-6-methyl-4-pyrimidinyl164 CH.sub.2 O 2-methyl-6-methoxymethyl-4-pyrimidinyl165 CH.sub.2 S 2-methyl-6-methoxymethyl-4-pyrimidinyl166 CH.sub.2 O 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl167 CH.sub.2 S 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl168 CH.sub.2 O 2-phenyl-4-pyrimidinyl169 CH.sub.2 S 2-phenyl-4-pyrimidinyl170 CH.sub.2 O 3,5-dimethyl-4-pyrimidinyl171 CH.sub.2 S 3,5-dimethyl-4-pyrimidinyl172 CH.sub.2 O 2-methylthio-6-trifluoromethyl-4-pyrimidinyl173 CH.sub.2 S 2-methylthio-6-trifluoromethyl-4-pyrimidinyl174 CH.sub.2 O 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl175 CH.sub.2 S 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl176 CH.sub.2 O 2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl177 CH.sub.2 S 2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl178 CH.sub.2 O 2-methyl-6-trifluoromethyl-4-pyrimidinyl179 CH.sub.2 S 2-methyl-6-trifluoromethyl-4-pyrimidinyl180 CH.sub.2 O 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl181 CH.sub.2 S 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl182 CH.sub.2 O 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl183 CH.sub.2 S 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl184 CH.sub.2 O 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl185 CH.sub.2 S 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl186 CH.sub.2 O 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl187 CH.sub.2 S 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl188 CH.sub.2 O 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl189 CH.sub.2 S 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl190 CH.sub.2 O 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl191 CH.sub.2 S 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl192 CH.sub.2 O 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl193 CH.sub.2 S 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl194 CH.sub.2 S 2-pyrimidinyl 62-64195 CH.sub.2 O 6-cyclopropyl-2-pyridyl196 CH.sub.2 S 6-cyclopropyl-2-pyridyl197 CH.sub.2 O 2-pyrazinyl198 CH.sub.2 S 2-pyrazinyl199 CH.sub.2 O 6-chloro-2-pyrazinyl200 CH.sub.2 S 6-chloro-2-pyrazinyl201 CH.sub.2 O 5-methyl-2-pyrazinyl202 CH.sub.2 S 5-methyl-2-pyrazinyl203 CH.sub.2 O 3-pyridazinyl204 CH.sub.2 S 3-pyridazinyl205 CH.sub.2 O 5-chloro-3-pyridazinyl206 CH.sub.2 S 5-chloro-3-pyridazinyl207 CH.sub.2 O 2-thienyl208 CH.sub.2 S 2-thienyl209 CH.sub.2 O 3-thienyl210 CH.sub.2 S 3-thienyl211 CH.sub.2 O 4-chloro-3-thienyl212 CH.sub.2 S 4-chloro-3-thienyl213 CH.sub.2 O 2-chloro-3-thienyl214 CH.sub.2 S 2-chloro-3-thienyl215 CH.sub.2 O 5-chloro-3-thienyl216 CH.sub.2 S 5-chloro-3-thienyl217 CH.sub.2 O 2-quinoxalinyl218 CH.sub.2 S 2-quinoxalinyl219 CH.sub.2 O 3-methyl-2-quinoxalinyl220 CH.sub.2 S 3-methyl-2-quinoxalinyl221 CH.sub.2 O 7,8-dimethyl-2-quinoxalinyl222 CH.sub.2 S 7,8-dimethyl-2-quinoxalinyl223 CH.sub.2 O 7,8-dichloro-2-quinoxalinyl224 CH.sub.2 S 7,8-dichloro-2-quinoxalinyl225 CH.sub.2 O 7-methyl-2-quinoxalinyl226 CH.sub.2 S 7-methyl-2-quinoxalinyl227 CH.sub.2 O 8-methyl-2-quinoxalinyl228 CH.sub.2 S 8-methyl-2-quinoxalinyl229 CH.sub.2 O 7-methoxy-2-qunioxalinyl230 CH.sub.2 S 7-methoxy-2-quinoxalinyl231 CH.sub.2 O 3-phenyl-5-isoxazolyl232 CH.sub.2 S 3-phenyl-5-isoxazolyl233 CH.sub.2 O 2-benzoxazolyl234 CH.sub.2 S 2-benzoxazolyl235 CH.sub.2 O 2-benzthiazolyl236 CH.sub.2 S 2-benzthiazolyl237 CH.sub.2 S 6-methyl-2-benzthiazolyl 86-88238 CH.sub.2 S 4-chloro-2-benzthiazolyl oil 4.6(S, 2H); 7, 55(S, 1H)239 CH.sub.2 S 5-chloro-2-benzthiazolyl 131-133240 CH.sub.2 S 6-chloro-2-benzthiazolyl 86-89241 CH.sub.2 S 6-ethoxy-2-benzthiazolyl242 CH.sub.2 S 5-trifluoromethyl-2-benzthiazolyl oil 4.6(S, 2H); 7.55(S, 1H)243 CH.sub.2 S 4,8-dimethyl-2-quinolyl244 CH.sub.2 O 4,8-dimethyl-2-quinolyl245 CH.sub.2 O 6-iso-butyl-2-pyridyl246 CH.sub.2 O 3-cyano-6-iso-butyl-2-pyridyl__________________________________________________________________________
TABLE 20__________________________________________________________________________ ##STR47##No. A Hetaryl mp NMR: .delta. (ppm)__________________________________________________________________________1 CH.sub.2S 4-pyridyl2 CH.sub.2O 6-methyl-2-pyridyl oil 3.95(S, 3H); 4.05 (S, 3H); 5.35(S, 2H)3 CH.sub.2S 6-methyl-2-pyridyl4 CH.sub.2O 6-ethyl-2-pyridyl5 CH.sub.2S 6-ethyl-2-pyridyl6 CH.sub.2O 6-n-propyl-2-pyridyl7 CH.sub.2S 6-n-propyl-2-pyridyl8 CH.sub.2O 6-iso-propyl-2-pyridyl9 CH.sub.2S 6-iso-propyl-2-pyridyl10 CH.sub.2O 6-n-butyl-2-pyridyl11 CH.sub.2S 6-n-butyl-2-pyridyl12 CH.sub.2O 6-tert.-butyl-2-pyridyl13 CH.sub.2S 6-tert.-butyl-2-pyridyl14 CH.sub.2O 6-n-pentyl-2-pyridyl15 CH.sub.2S 6-n-pentyl-2-pyridyl16 CH.sub.2O 6-n-hexyl-2-pyridyl17 CH.sub.2S 6-n-hexyl-2-pyridyl18 CH.sub.2O 6-phenyl-2-pyridyl19 CH.sub.2S 6-phenyl-2-pyridyl20 CH.sub.2O 6-benzyl-2-pyridyl21 CH.sub.2S 6-benzyl-2-pyridyl22 CH.sub.2S 6-benzyl-2-pyridyl23 CH.sub.2S 6-trifluoromethyl-2-pyridyl24 CH.sub.2O 6-methoxy-2-pyridyl25 CH.sub.2S 6-methoxy-2-pyridyl26 CH.sub.2O 6-chloro-2-pyridyl27 CH.sub.2S 6-chloro-2-pyridyl28 CH.sub.2O 3,6-dimethyl-2-pyridyl29 CH.sub.2S 3,6-dimethyl-2-pyridyl30 CH.sub.2O 3,6-diethyl-2-pyridyl31 CH.sub.2S 3,6-diethyl-2-pyridyl32 CH.sub.2O 4,6-dimethyl-2-pyridyl33 CH.sub.2S 4,6-dimethyl-2-pyridyl34 CH.sub.2O 5,6-dimethyl-2-pyridyl35 CH.sub.2S 5,6-dimethyl-2-pyridyl36 CH.sub.2O 4-phenyl-6-methyl-2-pyridyl37 CH.sub.2S 4-phenyl-6-methyl-2-pyridyl38 CH.sub.2O 4,6-diphenyl-2-pyridyl39 CH.sub.2S 4,6-diphenyl-2-pyridyl40 CH.sub.2O 3,4-dichloro-6-methyl-2-pyridyl41 CH.sub.2S 3,4-dichloro-6-methyl-2-pyridyl42 CH.sub.2O 3,4,5-trichloro-6-phenyl-2-pyridyl43 CH.sub.2S 3,4,5-trichloro-6-phenyl-2-pyridyl44 CH.sub.2O 4-trifluoromethyl-6-methyl-2-pyridyl45 CH.sub.2S 4-trifluoromethyl-6-methyl-2-pyridyl46 CH.sub.2O 3-acetyl-4,6-dimethyl-2-pyridyl47 CH.sub.2S 3-acetyl-4,6-dimethyl-2-pyridyl48 CH.sub.2O 3-cyano-6-methyl-2-pyridyl49 CH.sub.2S 3-cyano-6-methyl-2-pyridyl50 CH.sub.2O 3-cyano-6-ethyl-2-pyridyl51 CH.sub.2S 3-cyano-6-ethyl-2-pyridyl52 CH.sub.2O 3-cyano-6-n-propyl-2-pyridyl53 CH.sub.2S 3-cyano-6-n-propyl-2-pyridyl54 CH.sub.2O 3-cyano-6-iso-propyl-2-pyridyl55 CH.sub.2S 3-cyano-6-iso-propyl-2-pyridyl56 CH.sub.2O 3-cyano-6-cyclo-propyl-2-pyridyl57 CH.sub.2S 3-cyano-6-cyclo-propyl-2-pyridyl58 CH.sub.2O 3-cyano-6-n-butyl-2-pyridyl59 CH.sub.2S 3-cyano-6-n-butyl-2-pyridyl60 CH.sub.2O 3-cyano-6-tert.-butyl-2-pyridyl61 CH.sub.2S 3-cyano-6-tert.-butyl-2-pyridyl62 CH.sub.2O 3-cyano-6-cyclo-hexyl-2-pyridyl63 CH.sub.2S 3-cyano-6-cyclo-hexyl-2-pyridyl64 CH.sub.2O 3-cyano-6-phenyl-2-pyridyl65 CH.sub.2S 3-cyano-6-phenyl-2-pyridyl66 CH.sub.2O 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl67 CH.sub.2S 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl68 CH.sub.2O 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl69 CH.sub.2S 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl70 CH.sub.2O 3-cyano-4,6-dimethyl-2-pyridyl71 CH.sub.2S 3-cyano-4,6-dimethyl-2-pyridyl72 CH.sub.2O 3,5,6-trichloro-2-pyridyl73 CH.sub.2S 3,5,6-trichloro-2-pyridyl74 CH.sub.2O 5-trifluoromethyl-2-pyridyl75 CH.sub.2S 5-trifluoromethyl-2-pyridyl76 CH.sub.2O 3-chloro-5-trifluoromethyl-2-pyridyl77 CH.sub.2S 3-chloro-5-trifluoromethyl-2-pyridyl78 CH.sub.2O 2-quinolyl79 CH.sub.2S 2-quinolyl80 CH.sub.2O 3-methyl-2-quinolyl81 CH.sub.2S 3-methyl-2-quinolyl82 CH.sub.2O 4-methyl-2-quinolyl83 CH.sub.2S 4-methyl-2-quinolyl84 CH.sub.2O 4-ethyl-2-quinolyl85 CH.sub.2S 4-ethyl-2-quinolyl86 CH.sub.2O 4-phenyl-2-quinolyl87 CH.sub.2S 4-phenyl-2-quinolyl88 CH.sub.2O 6-methyl-2-quinolyl89 CH.sub.2S 6-methyl-2-quinolyl90 CH.sub.2O 6-chloro-2-quinolyl91 CH.sub.2S 6-chloro-2-quinolyl92 CH.sub.2O 8-methyl-2-quinolyl93 CH.sub.2S 8-methyl-2-quinolyl94 CH.sub.2O 8-chloro-2-quinolyl95 CH.sub.2S 8-chloro-2-quinolyl96 CH.sub.2O 4-ethoxycarbonyl-2-quinolyl97 CH.sub.2S 4-ethoxycarbonyl-2-quinolyl98 CH.sub.2O 3,4-dimethyl-2-quinolyl99 CH.sub.2S 3,4-dimethyl-2-quinolyl100 CH.sub.2O 4-methyl-8-methoxy-2-quinolyl101 CH.sub.2S 4-methyl-8-methoxy-2-quinolyl102 CH.sub.2O 4-phenyl-8-ethoxy-2-quinolyl103 CH.sub.2S 4-phenyl-8-ethoxy-2-quinolyl104 CH.sub.2O 4-methyl-8-chloro-2-quinolyl105 CH.sub.2S 4-methyl-8-chloro-2-quinolyl106 CH.sub.2O 4-methyl-8-fluoro-2-quinolyl107 CH.sub.2S 4-methyl-8-fluoro-2-quinolyl108 CH.sub.2O 4-quinolyl109 CH.sub.2S 4-quinolyl110 CH.sub.2O 2-methyl-4-quinolyl111 CH.sub.2S 2-methyl-4-quinolyl112 CH.sub.2O 2-trichloromethyl-4-quinolyl113 CH.sub.2S 2-trichloromethyl-4-quinolyl114 CH.sub.2O 2-trichloromethyl-2-quinolyl115 CH.sub.2S 2-trichloromethyl-2-quinolyl116 CH.sub.2O 2-iso-propyl-4-quinolyl117 CH.sub.2S 2-iso-propyl-4-quinolyl118 CH.sub.2O 2-n-pentyl-4-quinolyl119 CH.sub.2S 2-n-pentyl-4-quinolyl120 CH.sub.2O 2-phenyl-4-quinolyl121 CH.sub.2S 2-phenyl-4-quinolyl122 CH.sub.2O 2-methoxycarbonyl-4-quinolyl123 CH.sub.2S 2-methoxycarbonyl-4-quinolyl124 CH.sub.2O 2,6-dimethyl-4-quinolyl125 CH.sub.2S 2,6-dimethyl-4-quinolyl126 CH.sub.2O 2-methyl-6-chloro-4-quinolyl127 CH.sub.2S 2-methyl-6-chloro-4-quinolyl128 CH.sub.2O 2-methyl-6-fluoro-4-quinolyl129 CH.sub.2S 2-methyl-6-fluoro-4-quinolyl130 CH.sub.2O 8-quinolyl131 CH.sub.2S 8-quinolyl132 CH.sub.2O 2-methyl-8-quinolyl133 CH.sub.2S 2-methyl-8-quinolyl134 CH.sub.2O 5,7-dichloro-8-quinolyl135 CH.sub.2S 5,7-dichloro-8-quinolyl136 CH.sub.2O 4,6-dimethyl-2-pyrimidinyl137 CH.sub.2S 4,6-dimethyl-2-pyrimidinyl138 CH.sub.2O 4-trifluoromethyl-2-pyrimidinyl139 CH.sub.2S 4-trifluoromethyl-2-pyrimidinyl140 CH.sub.2O 4,5,6-trimethyl-2-pyrimidinyl141 CH.sub.2S 4,5,6-trimethyl-2-pyrimidinyl142 CH.sub.2O 4-benzyl-6-methyl-2-pyrimidinyl143 CH.sub.2S 4-benzyl-6-methyl-2-pyrimidinyl144 CH.sub.2O 4-methyl-6-phenyl-2-pyrimidinyl145 CH.sub.2S 4-methyl-6-phenyl-2-pyrimidinyl146 CH.sub.2O 4,5-dimethyl-5-chloro-2-pyrimidinyl147 CH.sub.2S 4,5-dimethyl-5-chloro-2-pyrimidinyl148 CH.sub.2O 2,6-dimethyl-4-pyrimidinyl149 CH.sub.2S 2,6-dimethyl-4-pyrimidinyl150 CH.sub.2O 2,6-bis-(trifluoromethyl)-4-pyrimidinyl151 CH.sub.2S 2,6-bis-(trifluoromethyl)-4-pyrimidinyl152 CH.sub.2O 2-chloromethyl-6-methyl-4-pyrimidinyl153 CH.sub.2S 2-chloromethyl-6-methyl-4-pyrimidinyl154 CH.sub.2O 2-methyl-6-chloromethyl-4-pyrimidinyl155 CH.sub.2S 2-methyl-6-chloromethyl-4-pyrimidinyl156 CH.sub.2O 2-iso-propyl-6-methyl-4-pyrimidinyl157 CH.sub.2S 2-iso-propyl-6-methyl-4-pyrimidinyl158 CH.sub.2O 2-iso-propyl-6-chloromethyl-4-pyrimidinyl159 CH.sub.2S 2-iso-propyl-6-chloromethyl-4-pyrimidinyl160 CH.sub.2O 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl161 CH.sub.2S 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl162 CH.sub.2O 2-cyclo-propyl-6-methyl-4-pyrimidinyl163 CH.sub.2S 2-cyclo-propyl-6-methyl-4-pyrimidinyl164 CH.sub.2O 2-methyl-6-methoxymethyl-4-pyrimidinyl165 CH.sub.2S 2-methyl-6-methoxymethyl-4-pyrimidinyl166 CH.sub.2O 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl167 CH.sub.2S 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl168 CH.sub.2O 2-phenyl-4-pyrimidinyl169 CH.sub.2S 2-phenyl-4-pyrimidinyl170 CH.sub.2O 3,5-dimethyl-4-pyrimidinyl171 CH.sub.2S 3,5-dimethyl-4-pyrimidinyl172 CH.sub.2O 2-methylthio-6-trifluoromethyl-4-pyrimidinyl173 CH.sub.2S 2-methylthio-6-trifluoromethyl-4-pyrimidinyl174 CH.sub.2O 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl175 CH.sub.2S 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl176 CH.sub.2O 2-methylthio-5-n-octyl-6-trifluoromethyl-4-pyrimidinyl177 CH.sub.2S 2-methylthio-5-n-octyl-6-trifluoromethyl-4-pyrimidinyl178 CH.sub.2O 2-methyl-6-trifluoromethyl-4-pyrimidinyl179 CH.sub.2S 2-methyl-6-trifluoromethyl-4-pyrimidinyl180 CH.sub.2O 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl181 CH.sub.2S 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl182 CH.sub.2O 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl183 CH.sub.2S 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl184 CH.sub.2O 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl185 CH.sub.2S 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl186 CH.sub.2O 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl187 CH.sub.2S 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl188 CH.sub.2O 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl189 CH.sub.2S 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl190 CH.sub.2O 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl191 CH.sub.2S 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl192 CH.sub.2O 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl193 CH.sub.2S 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl194 CH.sub.2S 2-pyrimidinyl195 CH.sub.2O 6-cyclopropyl-2-pyridyl196 CH.sub.2S 6-cyclopropyl-2-pyridyl197 CH.sub.2O 2-pyrazinyl198 CH.sub.2S 2-pyrazinyl199 CH.sub.2O 6-chloro-2-pyrazinyl200 CH.sub.2S 6-chloro-2-pyrazinyl201 CH.sub.2O 5-methyl-2-pyrazinyl202 CH.sub.2S 5-methyl-2-pyrazinyl203 CH.sub.2O 3-pyridazinyl204 CH.sub.2S 3-pyridazinyl205 CH.sub.2O 5-chloro-3-pyridazinyl206 CH.sub.2S 5-chloro-3-pyridazinyl207 CH.sub.2O 2-thienyl208 CH.sub.2S 2-thienyl209 CH.sub.2O 3-thienyl210 CH.sub.2S 3-thienyl211 CH.sub.2O 4-chloro-3-thienyl212 CH.sub.2S 4-chloro-3-thienyl213 CH.sub.2O 2-chloro-3-thienyl214 CH.sub.2S 2-chloro-3-thienyl215 CH.sub.2O 5-chloro-3-thienyl216 CH.sub.2S 5-chloro-3-thienyl217 CH.sub.2O 2-quinoxalinyl218 CH.sub.2S 2-quinoxalinyl219 CH.sub.2O 3-methyl-2-quinoxalinyl220 CH.sub.2S 3-methyl-2-quinoxalinyl221 CH.sub.2O 7,8-dimethyl-2-quinoxalinyl222 CH.sub.2S 7,8-dimethyl-2-quinoxalinyl223 CH.sub.2O 7,8-dichloro-2-quinoxalinyl224 CH.sub.2S 7,8-dichloro-2-quinoxalinyl225 CH.sub.2O 7-methyl-2-quinoxalinyl226 CH.sub.2S 7-methyl-2-quinoxalinyl227 CH.sub.2O 8-methyl-2-quinoxalinyl228 CH.sub.2S 8-methyl-2-quinoxalinyl229 CH.sub.2O 7-methoxy-2-quinoxalinyl230 CH.sub.2S 7-methoxy-2-quinoxalinyl231 CH.sub.2O 3-phenyl-5-isoxazolyl232 CH.sub.2S 3-phenyl-5-isoxazolyl233 CH.sub.2O 2-benzoxazolyl234 CH.sub.2S 2-benzoxazolyl235 CH.sub.2O 2-benzthiazolyl236 CH.sub.2S 2-benzthiazolyl237 CH.sub.2S 6-methyl-2-benzthiazolyl (non-polar isomer) oil 3.9(S, 3H); 4.0(S, 3H); 4.55(S, 2H)238 CH.sub.2S 4-chloro-2-benzthiazolyl239 CH.sub.2S 5-chloro-2-benzthiazolyl240 CH.sub.2S 6-chloro-2-benzthiazolyl241 CH.sub.2S 6-ethoxy-2-benzthiazolyl242 CH.sub.2S 5-trifluoromethyl-2-benzthiazolyl243 CH.sub.2S 4,8-dimethyl-2-quinolyl244 CH.sub.2O 4,8-dimethyl-2-quinolyl245 CH.sub.2O 6-iso-butyl-2-pyridyl246 CH.sub.2O 3-cyano-6-iso-butyl-2-pyridyl__________________________________________________________________________
TABLE 21__________________________________________________________________________ ##STR48##No. A Hetaryl mp NMR: .delta. (ppm)__________________________________________________________________________ 1 CH.sub.2 S 4-pyridyl 2 CH.sub.2 O 6-methyl-2-pyridyl oil 3.95(S, 3H); 4.05 (S, 3H); 5.35(S, 2H) 3 CH.sub.2 S 6-methy-2-pyridyl 4 CH.sub.2 O 6-ethyl-2-pyridyl 5 CH.sub.2 S 6-ethyl-2-pyridyl 6 CH.sub.2 O 6-n-propyl-2-pyridyl 7 CH.sub.2 S 6-n-propyl-2-pyridyl 8 CH.sub.2 O 6-iso-propyl-2-pyridyl 9 CH.sub.2 S 6-iso-propyl-2-pyridyl 10 CH.sub.2 O 6-n-butyl-2-pyridyl 11 Ch.sub.2 S 6-n-butyl-2-pyridyl 12 CH.sub.2 O 6-tert.-butyl-2-pyridyl 13 CH.sub.2 S 6-tert.-butyl-2-pyridyl 14 CH.sub.2 O 6-n-pentyl-2-pyridyl 15 CH.sub.2 S 6-n-pentyl-2-pyridyl 16 CH.sub.2 O 6-n-hexyl-2-pyridyl 17 CH.sub.2 S 6-n-hexyl-2-pyridyl 18 CH.sub.2 O 6-phenyl-2-pyridyl 19 CH.sub.2 S 6-phenyl-2-pyridyl 20 CH.sub.2 O 6-benzyl-2-pyridyl 21 CH.sub.2 S 6-benzyl-2-pyridyl 22 CH.sub.2 S 6-benzyl-2-pyridyl 23 CH.sub.2 S 6-trifluoromethyl-2-pyridyl 24 CH.sub.2 O 6-methoxy-2-pyridyl 25 CH.sub.2 S 6-methoxy-2-pyridyl 26 CH.sub.2 O 6-chloro-2-pyridyl 27 CH.sub.2 S 6-chloro-2-pyridyl 28 CH.sub.2 O 3,6-dimethyl-2-pyridyl 29 CH.sub.2 S 3,6-dimethyl-2-pyridyl 30 CH.sub.2 O 3,6-diethyl-2-pyridyl 31 CH.sub.2 S 3,6-diethyl-2-pyridyl 32 CH.sub.2 O 4,6-dimethyl-2-pyridyl 33 CH.sub.2 S 4,6-dimethyl-2-pyridyl 34 CH.sub.2 O 5,6-dimethyl-2-pyridyl 35 CH.sub.2 S 5,6-dimethyl-2-pyridyl 36 CH.sub.2 O 4-phenyl-6-methyl-2-pyridyl 37 CH.sub.2 S 4-phenyl-6-methyl-2-pyridyl 38 CH.sub.2 O 4,6-diphenyl-2-pyridyl 39 CH.sub.2 S 4,6-diphenyl-2-pyridyl 40 CH.sub.2 O 3,4-dichloro-6-methyl-2-pyridyl 41 CH.sub.2 S 3,4-dichloro-6-methyl-2-pyridyl 42 CH.sub.2 O 3,4,5-trichloro-6-phenyl-2-pyridyl 43 CH.sub.2 S 3,4,5-trichloro-6-phenyl-2-pyridyl 44 CH.sub.2 O 4-trifluoromethyl-6-methyl-2-pyridyl 45 CH.sub.2 S 4-trifluoromethyl-6-methyl-2-pyridyl 46 CH.sub.2 O 3-acetyl-4,6-dimethyl-2-pyridyl 47 CH.sub.2 S 3-acetyl-4,6-dimethyl-2-pyridyl 48 CH.sub.2 O 3-cyano-6-methyl-2-pyridyl 49 CH.sub.2 S 3-cyano-6-methyl-2-pyridyl 50 CH.sub.2 O 3-cyano-6-ethyl-2-pyridyl 51 CH.sub.2 S 3-cyano-6-ethyl-2-pyridyl 52 CH.sub.2 O 3-cyano-6-n-propyl-2-pyridyl 53 CH.sub.2 S 3-cyano-6-n-propyl-2-pyridyl 54 CH.sub.2 O 3-cyano-6-iso-propyl-2-pyridyl 55 CH.sub.2 S 3-cyano-6-iso-propyl-2-pyridyl 56 CH.sub.2 O 3-cyano-6-cyclo-propyl-2-pyridyl 57 CH.sub.2 S 3-cyano-6-cyclo-propyl-2-pyridyl 58 CH.sub.2 O 3-cyano-6-n-butyl-2-pyridyl 59 CH.sub.2 S 3-cyano-6-n-butyl-2-pyridyl 60 CH.sub.2 O 3-cyano-6-tert.-butyl-2-pyridyl 61 CH.sub.2 S 3-cyano-6-tert.-butyl-2-pyridyl 62 CH.sub.2 O 3-cyano-6-cyclo-hexyl-2-pyridyl 63 CH.sub.2 S 3-cyano-6-cyclo-hexyl-2-pyridyl 64 CH.sub.2 O 3-cyano-6-phenyl-2-pyridyl 65 CH.sub.2 S 3-cyano-6-phenyl-2-pyridyl 66 CH.sub.2 O 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl 67 CH.sub.2 S 3-methyloxycarbonyl-6-iso-propyl-2-pyridyl 68 CH.sub.2 O 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl 69 CH.sub.2 S 3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl 70 CH.sub.2 O 3-cyano-4,6-dimethyl-2-pyridyl 71 CH.sub.2 S 3-cyano-4,6-dimethyl-2-pyridyl 72 CH.sub.2 O 3,5,6-trichloro-2-pyridyl 73 CH.sub.2 S 3,5,6-trichloro-2-pyridyl 74 CH.sub.2 O 5-trifluoromethyl-2-pyridyl 75 CH.sub.2 S 5-trifluoromethyl-2-pyridyl 76 CH.sub.2 O 3-chloro-5-trifluoromethyl-2-pyridyl 77 CH.sub.2 S 3-chloro-5-trifluoromethyl-2-pyridyl 78 CH.sub.2 O 2-quinolyl 79 CH.sub.2 S 2-quinolyl 80 CH.sub.2 O 3-methyl-2-quinolyl 81 CH.sub.2 S 3-methyl-2-quinolyl 82 CH.sub.2 O 4-methyl-2-quinolyl 83 CH.sub.2 S 4-methyl-2-quinolyl 84 CH.sub.2 O 4-ethyl-2-quinolyl 85 CH.sub.2 S 4-ethyl-2-quinolyl 86 CH.sub.2 O 4-phenyl-2-quinolyl 87 CH.sub.2 S 4-phenyl-2-quinolyl 88 CH.sub.2 O 6-methyl-2-quinolyl 89 CH.sub.2 S 6-methyl-2-quinolyl 90 CH.sub.2 O 6-chloro-2-quinolyl 91 CH.sub.2 S 6-chloro-2-quinolyl 92 CH.sub.2 O 8-methyl-2-quinolyl 93 CH.sub.2 S 8-methyl-2-quinolyl 94 CH.sub.2 O 8-chloro-2-quinolyl 95 CH.sub.2 S 8-chloro-2-quinolyl 96 CH.sub.2 O 4-Ethoxycarbonyl-2-quinolyl 97 CH.sub.2 S 4-Ethoxycarbonyl-2-quinolyl 98 CH.sub.2 O 3,4-dimethyl-2-quinolyl 99 CH.sub.2 S 3,4-dimethyl-2-quinolyl100 CH.sub.2 O 4-methyl-8-methoxy-2-quinolyl101 CH.sub.2 S 4-methyl-8-methoxy-2-quinolyl102 CH.sub.2 O 4-phenyl-8-ethoxy-2-quinolyl103 CH.sub.2 S 4-phenyl-8-ethoxy-2-quinolyl104 CH.sub.2 O 4-methyl-8-chloro-2-quinolyl105 CH.sub.2 S 4-methyl-8-chloro-2-quinolyl106 CH.sub.2 O 4-methyl-8-fluoro-2-quinolyl107 CH.sub.2 S 4-methyl-8-fluoro-2-quinolyl108 CH.sub.2 O 4-quinolyl109 CH.sub.2 S 4-quinolyl110 CH.sub.2 O 2-methyl-4-quinolyl111 CH.sub.2 S 2-methyl-4-quinolyl112 CH.sub.2 O 2-trichloromethyl-4-quinolyl113 CH.sub.2 S 2-trichloromethyl-4-quinolyl114 CH.sub.2 O 2-trifluoromethyl-2-quinolyl115 CH.sub.2 S 2-trifluoromethyl-2-quinolyl116 CH.sub.2 O 2-iso-propyl-4-quinolyl117 CH.sub.2 S 2-iso-propyl-4-quinolyl118 CH.sub.2 O 2-n-pentyl-4-quinolyl119 CH.sub.2 S 2-n-pentyl-4-quinolyl120 CH.sub.2 O 2-phenyl-4-quinolyl121 CH.sub.2 S 2-phenyl-4-quinolyl122 CH.sub.2 O 2-methoxycarbonyl-4-quinolyl123 CH.sub.2 S 2-methoxycarbonyl-4-quinolyl124 CH.sub.2 O 2,6-dimethyl-4-quinolyl125 CH.sub.2 S 2,6-dimethyl-4-quinolyl126 CH.sub.2 O 2-methyl-6-chloro-4-quinolyl127 CH.sub.2 S 2-methyl-6-chloro-4-quinolyl128 CH.sub.2 O 2-methyl-6-fluoro-4-quinolyl129 CH.sub.2 S 2-methyl-6-fluoro-4-quinolyl130 CH.sub.2 O 8-quinolyl131 CH.sub.2 S 8-quinolyl132 CH.sub.2 O 2-methyl-8-quinolyl133 CH.sub.2 S 2-methyl-8-quinolyl134 CH.sub.2 O 5,7-dichloro-8-quinolyl135 CH.sub.2 S 5,7-dichloro-8-quinolyl136 CH.sub.2 O 4,6-dimethyl-2-pyrimidinyl137 CH.sub.2 S 4,6-dimethyl-2-pyrimidinyl138 CH.sub.2 O 4-trifluoromethyl-2-pyrimidinyl139 CH.sub.2 S 4-trifluoromethyl-2-pyrimidinyl140 CH.sub.2 O 4,5,6-trimethyl-2-pyrimidinyl141 CH.sub.2 S 4,5,6-trimethyl-2-pyrimidinyl142 CH.sub.2 O 4-benzyl-6-methyl-2-pyrimidinyl143 CH.sub.2 S 4-benzyl-6-methyl-2-pyrimidinyl144 CH.sub.2 O 4-methyl-6-phenyl-2-pyrimidinyl145 CH.sub.2 S 4-methyl-6-phenyl-2-pyrimidinyl146 CH.sub.2 O 4,6-dimethyl-5-chloro-2-pyrimidinyl147 CH.sub.2 S 4,6-dimethyl-5-chloro-2-pyrimidinyl148 CH.sub.2 O 2,6-dimethyl-4-pyrimidinyl149 CH.sub.2 S 2,6-dimethyl-4-pyrimidinyl150 CH.sub.2 O 2,6-bis-(trifluoromethyl)-4-pyrimidinyl151 CH.sub.2 S 2,6-bis-(trifluoromethyl)-4-pyrimidinyl152 CH.sub.2 O 2-chloromethyl-6-methyl-4-pyrimidinyl153 CH.sub.2 S 2-chloromethyl-6-methyl-4-pyrimidinyl154 CH.sub.2 O 2-methyl-6-chloromethyl-4-pyrimidinyl155 CH.sub.2 S 2-methyl-6-chloromethyl-4-pyrimidinyl156 CH.sub.2 O 2-iso-propyl-6-methyl-4-pyrimidinyl157 CH.sub.2 S 2-iso-propyl-6-methyl-4-pyrimidinyl158 CH.sub.2 O 2-iso-propyl-6-chloromethyl-4-pyrimidinyl159 CH.sub.2 S 2-iso-propyl-6-chloromethyl-4-pyrimidinyl160 CH.sub.2 O 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl161 CH.sub.2 S 2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl162 CH.sub.2 O 2-cyclo-propyl-6-methyl-4-pyrimidinyl163 CH.sub.2 S 2-cyclo-propyl-6-methyl-4-pyrimidinyl164 CH.sub.2 O 2-methyl-6-methoxymethyl-4-pyrimidinyl165 CH.sub.2 S 2-methyl-6-methoxymethyl-4-pyrimidinyl166 CH.sub.2 O 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl167 CH.sub.2 S 2-iso-propyl-6-methoxymethyl-4-pyrimidinyl168 CH.sub.2 O 2-phenyl-4-pyrimidinyl169 CH.sub.2 S 2-phenyl-4-pyrimidinyl170 CH.sub.2 O 3,5-dimethyl-4-pyrimidinyl171 CH.sub.2 S 3,5-dimethyl-4-pyrimidinyl172 CH.sub.2 O 2-methylthio-6-trifluoromethyl-4-pyrimidinyl173 CH.sub.2 S 2-methylthio-6-trifluoromethyl-4-pyrimidinyl174 CH.sub.2 O 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl175 CH.sub.2 S 2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl176 CH.sub.2 O 2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl177 CH.sub.2 S 2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl178 CH.sub.2 O 2-methyl-6-trifluoromethyl-4-pyrimidinyl179 CH.sub.2 S 2-methyl-6-trifluoromethyl-4-pyrimidinyl180 CH.sub.2 O 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl181 CH.sub.2 S 2-n-propyl-6-trifluoromethyl-4-pyrimidinyl182 CH.sub.2 O 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl183 CH.sub.2 S 2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl184 CH.sub.2 O 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl185 CH.sub.2 S 2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl186 CH.sub.2 O 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl187 CH.sub.2 S 2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl188 CH.sub.2 O 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl189 CH.sub.2 S 2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl190 CH.sub.2 O 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl191 CH.sub.2 S 2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl192 CH.sub.2 O 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl193 CH.sub.2 S 2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl194 CH.sub.2 S 2-pyrimidinyl195 CH.sub.2 O 6-cyclopropyl-2-pyridyl196 CH.sub.2 S 6-cyclopropyl-2-pyridyl197 CH.sub.2 O 2-pyrizinyl198 CH.sub.2 S 2-pyrazinyl199 CH.sub.2 O 6-chloro-2-pyrazinyl200 CH.sub.2 S 6-chloro-2-pyrazinyl201 CH.sub.2 O 5-methyl-2-pyrazinyl202 CH.sub.2 S 5-methyl-2-pyrazinyl203 CH.sub.2 O 3-pyridazinyl204 CH.sub.2 S 3-pyridazinyl205 CH.sub.2 O 5-chloro-3-pyridazinyl206 CH.sub.2 S 5-chloro-3-pyridazinyl207 CH.sub.2 O 2-thienyl208 CH.sub.2 S 2-thienyl209 CH.sub.2 O 3-thienyl210 CH.sub.2 S 3-thienyl211 CH.sub.2 O 4-chloro-3-thienyl212 CH.sub.2 S 4-chloro-3-thienyl213 CH.sub.2 O 2-chloro-3-thienyl214 CH.sub.2 S 2-chloro-3-thienyl215 CH.sub.2 O 5-chloro-3-thienyl216 CH.sub.2 S 5-chloro-3-thienyl217 CH.sub.2 O 2-quinoxalinyl218 CH.sub.2 S 2-quinoxalinyl219 CH.sub.2 O 3-methyl-2-quinxalinyl220 CH.sub.2 S 3-methyl-2-quinxalinyl221 CH.sub.2 O 7,8-dimethyl-2-quinoxalinyl222 CH.sub.2 S 7,8-dimethyl-2-quinoxalinyl223 CH.sub.2 O 7,8-dichloro-2-quinoxalinyl224 CH.sub.2 S 7,8-dichloro-2-quinoxalinyl225 CH.sub.2 O 7-methyl-2-quinoxalinyl226 CH.sub.2 S 7-methyl-2-quinoxalinyl227 CH.sub.2 O 8-methyl-2-quinoxalinyl228 CH.sub.2 S 8-methyl-2-quinoxalinyl229 CH.sub.2 O 7-methoxy-2-quinoxalinyl230 CH.sub.2 S 7-methoxy-2-quinoxalinyl231 CH.sub.2 O 3-phenyl-5-isoxazolyl232 CH.sub.2 S 3-phenyl-5-isoxazolyl233 CH.sub.2 O 2-benzoxazolyl234 CH.sub.2 S 2-benzoxazolyl235 CH.sub.2 O 2-benzthiazolyl236 CH.sub.2 S 2-benzthiazolyl237 CH.sub.2 S 6-methyl-2-benzthiazolyl (non-polar isomer) oil 3.9(S, 3H); 4.0(S, 3H); 4, 55(S, 2H)238 CH.sub.2 S 4-chloro-2-benzthiazolyl239 CH.sub.2 S 5-chloro-2-benzthiazolyl240 CH.sub.2 S 6-chloro-2-benzthiazolyl241 CH.sub.2 S 6-Ethoxy-2-benzthiazolyl242 CH.sub.2 S 5-trifluoromethyl-2-benzthiazolyl243 CH.sub.2 S 4,8-dimethyl-2-quinolyl244 CH.sub.2 O 4,8-dimethyl-2-quinolyl245 CH.sub.2 O 6-iso-butyl-2-pyridyl246 CH.sub.2 O 3-cyano-6-iso-butyl-2-pyridyl__________________________________________________________________________
TABLE 22__________________________________________________________________________ ##STR49##No. Z.sup.1 Z.sup.2 U A mp NMR__________________________________________________________________________ 1 2-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 CH.sub.2 2 2-OCH.sub.3 H HCOCH.sub.3 CHCH 3 2-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 O 4 2-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 OCO 5 2-OCH.sub.3 H NOCH.sub.3 CH.sub.2 CH.sub.2 6 2-OCH.sub.3 H NOCH.sub.3 CHCH 7 2-OCH.sub.3 H NOCH.sub.3 CH.sub.2 O 8 2-OCH.sub.3 H NOCH.sub.3 CH.sub.2 OCO 9 2-OCH.sub.3 H CHCH.sub.3 CH.sub.2 CH.sub.210 2-OCH.sub.3 H CHCH.sub.3 CHCH11 2-OCH.sub.3 H CHCH.sub.3 CH.sub.2 O12 2-OCH.sub.3 H CHCH.sub.3 CH.sub.2 OCO13 4-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 CH.sub. 214 4-OCH.sub.3 H HCOCH.sub.3 CHCH15 4-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 O16 4-OCH.sub.3 H HCOCH.sub.3 CH.sub.2 OCO17 4-OCH.sub.3 H NOCH.sub.3 CH.sub.2 CH.sub.218 4-OCH.sub.3 H NOCH.sub.3 CHCH19 4-OCH.sub.3 H NOCH.sub.3 CH.sub.2 O20 4-OCH.sub.3 H NOCH.sub.3 CH.sub.2 OCO21 4-OCH.sub.3 H CHCH.sub.3 CH.sub.2 CH.sub.222 4-OCH.sub.3 H CHCH.sub.3 CHCH23 4-OCH.sub.3 H CHCH.sub.3 CH.sub.2 O24 4-OCH.sub.3 H CHCH.sub.3 CH.sub.2 OCO25 6-N(CH.sub.3).sub.2 H HCOCH.sub.3 CH.sub.2 CH.sub.226 6-N(CH.sub.3).sub.2 H HCOCH.sub.3 CHCH27 6-N(CH.sub.3).sub.2 H HCOCH.sub.3 CH.sub.2 O28 6-N(CH.sub.3).sub.2 H HCOCH.sub.3 CH.sub.2 OCO29 6-N(CH.sub.3).sub.2 H NOCH.sub.3 CH.sub.2 CH.sub.230 6-N(CH.sub.3).sub.2 H NOCH.sub.3 CHCH31 6-N(CH.sub.3).sub.2 H NOCH.sub.3 CH.sub.2 O32 6-N(CH.sub.3).sub.2 H NOCH.sub. 3 CH.sub.2 O33 6-N(CH.sub.3).sub.2 H CHCH.sub.3 CH.sub.2 CH.sub.234 6-N(CH.sub.3).sub.2 H CHCH.sub.3 CHCH35 6-N(CH.sub.3).sub.2 H CHCH.sub.3 CH.sub.2 O36 6-N(CH.sub.3).sub.2 H CHCH.sub.3 CH.sub.2 OCO37 5-NO.sub.2 6-OCH.sub.3 HCOCH.sub.3 CH.sub.2 CH.sub.238 5-NO.sub.2 6-OCH.sub.3 HCOCH.sub.3 CHCH39 5-NO.sub.2 6-OCH.sub.3 HCOCH.sub.3 CH.sub.2 O40 5-NO.sub.2 6-OCH.sub.3 HCOCH.sub.3 CH.sub.2 OCO41 5-NO.sub.2 6-OCH.sub.3 NOCH.sub.3 CH.sub.2 CH.sub.242 5-NO.sub.2 6-OCH.sub.3 NOCH.sub.3 CHCH43 5-NO.sub.2 6-OCH.sub.3 NOCH.sub.3 CH.sub.2 O44 5-NO.sub.2 6-OCH.sub.3 NOCH.sub.3 CH.sub.2 OCO45 5-NO.sub.2 6-OCH.sub.3 CHCH.sub.3 CH.sub.2 CH.sub.246 5-NO.sub.2 6-OCH.sub.3 CHCH.sub.3 CHCH47 5-NO.sub.2 6-OCH.sub.3 CHCH.sub.3 CH.sub.2 O48 5-NO.sub.2 6-OCH.sub.3 CHCH.sub.3 CH.sub.2 OCO49 5-NO.sub.2 H HCOCH.sub.3 OCH.sub.250 5-NO.sub.2 H NOCH.sub.3 OCH.sub.251 5-NO.sub.2 H CHCH.sub.3 OCH.sub.252 4-NO.sub.2 H HCOCH.sub.3 OCH.sub.253 4-NO.sub.2 H NOCH.sub.3 OCH.sub.254 4-NO.sub.2 H CHCH.sub.3 OCH.sub.255 2-CO.sub.2 CH.sub.3 H HCOCH.sub.3 OCH.sub.256 2-CO.sub.2 CH.sub.3 H NOCH.sub.3 OCH.sub.257 2-CO.sub.2 CH.sub.3 H CHCH.sub.3 OCH.sub.258 4-OCH.sub.3 H HCOCH.sub.3 OCH.sub.259 4-OCH.sub.3 H NOCH.sub.3 OCH.sub.260 4-OCH.sub.3 H CHCH.sub.3 OCH.sub.261 4-OCH.sub.3 5-Br HCOCH.sub.3 OCH.sub.262 4-OCH.sub.3 5-Br NOCH.sub.3 OCH.sub.263 4-OCH.sub.3 5-Br CHCH.sub.3 OCH.sub.264 CH.sub.2 C.sub.6 H.sub.5 H HCOCH.sub.3 OCH.sub.265 CH.sub.2 C.sub.6 H.sub.5 H NOCH.sub.3 OCH.sub.266 CH.sub.2 C.sub.6 H.sub.5 H CHCH.sub.3 OCH.sub.2__________________________________________________________________________
In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia solani in cotton,
Ustilago species in cereals and sugar cane,
Venturia inaeualis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seed, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of the active ingredient.
The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.
The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials (timber), e.g., against Paecilomyces variotii. When the active ingredients are used for treating seed, rates of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally sufficient.
The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. A solution of 90 parts by weight of compound no. 2/77 and 10 parts by weight of N-methyl-.alpha.-pyrrolidone, which is suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 4/65, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and I mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of compound no. 13/8, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
IV. An aqueous dispersion of 20 parts by weight of compound no. 19/2, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210.degree. and 280.degree. C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
V. A hammer-milled mixture of 80 parts by weight of compound no. 19/26, 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 2111 and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 2/14, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 2/24, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 2/77, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.
Methyloxime (B) disclosed in DE 36 23 921, and 2-phenyloxymethylenephenylglyoxylic acid-O-methyloxime (C) disclosed in DE 36 23 921 were used for comparison purposes.
USE EXAMPLE 1
Action on Plasmopara viticola
Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24.degree. C. and then in a greenhouse for 5 days at from 20.degree. to 30.degree. C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves. The results show that active ingredients 2/77, 4/65, 13/8, 19/2 and 19/26, applied as 0.006 wt % spray liquors, had a better fungicidal action (85%) than the prior art active ingredients A, B and C (60%).
USE EXAMPLE 2
Action on Pyrenophora teres
Barley seedlings of the "Igri" variety were sprayed to runoff at the 2-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres and placed for 48 hours in a high-humidity climatic cabinet kept at 18.degree. C. The plants were then cultivated for a further 5 days in the greenhouse at 20.degree.-22.degree. C. and a relative humidity of 70%. The extent of fungus spread was then determined.
The results show that active ingredients 2/11, 2/14, 2/24, 2/77, 2/84, 2/456, 2/473, 2/474, 4/8, 4/65, 7/8, 7/66, 13/9, 13/10, 13/65, 13/66, 19/2, 19/26, 19/194, 19/237, 19/238, 19/239, 19/240 and 19/242, applied as 0.05% spray liquors, had a better fungicidal action (95%) than prior art active ingredients B (60%) and C (50%).
The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.
Examples of injurious insects belonging to the Lepidoptera order are Agrotis upsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographs gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molests, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis.
Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria.
Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa.
Examples from the Thysanoptera order are Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.
Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testundinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.
Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.
Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidocivne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
When the active ingredients are used for combating pests, the concentration of the active ingredients in the finished formulations may vary over a wide range. Generally, they are from 0.0001 to 10, and preferably from 0.001 to 0.1, %.
The active ingredients may also successfully be used in the ultra-low-volume (ULV) method, where it is possible to apply formulations containing more than 95 wt % of active ingredient, or even the active ingredient without additives.
In the open, the amount of active ingredient applied is for example from 0.01 to 10, particularly from 0.01 to 1.0, kg/ha.
Claims
  • 1. A compound of the formula ##STR50## wherein U is .dbd.CH.sub.2, .dbd.CHCH.sub.3, or .dbd.CHCH.sub.2 CH.sub.3 ; X is methyl; and m is 0, 1, or 2.
  • 2. A fungicidal composition containing a fungicidally effective amount of a compound according to claim 1 and an inert carrier therefor.
  • 3. A process for combatting fungi comprising applying to the fungi, or to the plants, materials, seeds, or soil threatened by fungus attack, a fungicidally effective amount of a compound according to claim 1.
  • 4. A compound according to claim 1 wherein U is .dbd.CHCH.sub.3 and m is 0.
  • 5. A compound according to claim 1 wherein U is .dbd.CHCH.sub.3 and X.sub.m is 2-methyl.
  • 6. A compound according to claim 1, wherein U is .dbd.CHCH.sub.3 and X.sub.m is 2,5-dimethyl.
Priority Claims (1)
Number Date Country Kind
3933891 Oct 1989 DEX
Parent Case Info

This application is continuation of application Ser. No. 07/595,413, filed on Oct. 11, 1990, now abandoned.

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Continuations (1)
Number Date Country
Parent 595413 Oct 1990