Lepidoptericidal isothiourea compounds

BACKGROUND OF THE INVENTION
Lepidoptericidal isothiuronium compounds have been disclosed in the prior art particularly those described in U.S. Pat. Nos. 3,969,511 and 4,062,892 and have the formula ##STR2## These compounds have a major disadvantage in that they show high levels of phytotoxic activity and thus, although controlling lepidoptera in the crop to be protected, are detrimental to the crop itself. To overcome this problem, applicants have discovered that substitution of the active hydrogen on the above type of isothiuronium and urea compounds with certain specific, relatively easily cleaved groups can lessen or eliminate phytotoxic effects of the parent compound while maintaining, and in some cases enhancing, the lepidoptericidal activity of the compound.
No prior art has been discovered which teaches or suggests the result that applicants have achieved.
DESCRIPTION OF THE INVENTION
The present invention is a novel group of compounds which may generally be described as certain isothioureas which are active lepidoptericides. Compounds of the present invention are represented by the generic formula ##STR3## wherein R and R.sub.1 are independently selected from the group consisting of:
C.sub.2 -C.sub.10 alkyl, preferably C.sub.5 -C.sub.9 alkyl, more preferably C.sub.6 -C.sub.8 alkyl,
C.sub.2 -C.sub.10 alkoxyalkyl, preferably C.sub.5 -C.sub.9 alkoxyalkyl, more preferably C.sub.6 -C.sub.8 alkoxyalkyl and phenyl and
R and R.sub.1 together contain from 12 to 22 carbon atoms;
wherein R.sub.2 is selected from the group consisting of:
C.sub.1 -C.sub.14 alkyl, preferably C.sub.1 -C.sub.6 alkyl, more preferably C.sub.1 -C.sub.3 alkyl,
C.sub.3 -C.sub.10 alkenyl, preferably C.sub.3 -C.sub.5 alkenyl, more preferably C.sub.2 -C.sub.3 alkenyl,
C.sub.3 -C.sub.4 alkynyl,
C.sub.2 -C.sub.4 hydroxyalkyl, preferably C.sub.2 -C.sub.3 hydroxyalkyl,
C.sub.2 -C.sub.6 alkylthioalkyl, preferably C.sub.2 -C.sub.4 alkylthioalkyl,
C.sub.2 -C.sub.6 alkyloxyalkyl, preferably C.sub.2 -C.sub.4 alkylthioalkyl,
(CH.sub.2).sub.n [X(CH.sub.2).sub.n ] y where n=1 or 2, X is O or S and y=1-4, preferably 1-2, ##STR4## where n=1-10, preferably 1-5, more preferably 1-3, phenyl and
phenethyl;
wherein R.sub.3 is selected from the group consisting of:
carboalkoxyalkyl wherein the alkyl is C.sub.1 -C.sub.4 alkyl, preferably C.sub.1 -C.sub.2 alkyl,
alkylketoalkyl wherein the alkyl is C.sub.1 -C.sub.4 alkyl, preferably C.sub.1 -C.sub.2 alkyl, hydroxyalkenyl wherein the alkenyl is C.sub.3 -C.sub.4 alkenyl,
hydroxyalkyl wherein the alkyl is C.sub.1 -C.sub.12 alkyl, preferably C.sub.1 -C.sub.6 alkyl, more preferably C.sub.1 -C.sub.3 alkyl,
formylhydroxymethyl,
hydroxyhaloethyl wherein the halo is chloro, bromo or iodo, preferably chloro or bromo, more preferably chloro,
substituted phenoxyalkyl wherein the alkyl is C.sub.1 -C.sub.2 alkyl, preferably C.sub.1 alkyl and the substituents are p-methoxy, Cl, NO.sub.3 or CN, ##STR5## wherein R.sup.1 is --OH, --NH.sub.2 or C.sub.1 -C.sub.4 alkoxy, preferably methoxy, ##STR6## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR7## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR8## wherein B is a basic cation, preferably an organic basic cation, more preferably an organic basic cation selected from the group consisting of ##STR9## wherein R.sub.4 is selected from the group consisting of: --H,
--C.sub.1 -C.sub.22 alkyl, preferably C.sub.1 -C.sub.12 alkyl,
more preferably C.sub.1 -C.sub.8 alkyl and
most preferably C.sub.1 -C.sub.6 alkyl,
hydroxyethyl,
naphthyl,
phenyl,
substituted phenyl wherein the substituents are independently selected from the group of halogen, preferably chlorine, C.sub.1 -C.sub.5 alkyl,
preferably C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.5 alkoxy,
preferably C.sub.1 -C.sub.2 alkoxy, nitro, cyano and --CF.sub.3, ##STR10## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR11## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR12## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR13## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR14## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR15## wherein x is 1 to 8 and R, R.sub.1 and R.sub.2 are as defined above, ##STR16## wherein m is 2 or 3 and R, R.sub.1 and R.sub.2 are as defined above, ##STR17## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR18## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR19## wherein X is selected from the group consisting of: O, S, NH, and NR.sub.11 ;
Y is hydrogen or methyl; and
R.sub.10 is selected from the group consisting of:
H,
C.sub.1 -C.sub.18 alkyl, preferably C.sub.1 -C.sub.8 alkyl, more preferably C.sub.1 -C.sub.2 alkyl,
C.sub.3 -C.sub.4 alkenyl,
C.sub.3 -C.sub.4 alkynyl,
C.sub.2 -C.sub.6 haloalkyl, preferably C.sub.2 -C.sub.3 haloalkyl,
C.sub.3 -C.sub.8 cycloalkyl,
C.sub.7 -C.sub.20 polycycloalkyl,
C.sub.2 -C16 polyalkoxyalkyl,
C.sub.2 -C.sub.6 hydroxyalkyl,
C.sub.3 -C.sub.10 alkoxyalkyl,
C.sub.3 -C.sub.8 carboalkoxyalkyl,
C.sub.4 -C.sub.8 cycloalkylalkyl,
C.sub.4 -C.sub.8 alkylcycloalkyl, preferably C.sub.6 -C.sub.8 alkylcycloalkyl,
C.sub.4 -C.sub.7 cycloalkylimino,
C.sub.2 -C.sub.10 alkylimino,
C.sub.1 -C.sub.3 alkylamino,
C.sub.4 -C.sub.12 dialkylaminoalkyl,
C.sub.6 -C.sub.10 cycloalkenyl,
phenyl,
alkylphenyl wherein the alkyl is C.sub.1 -C.sub.4,
parachloroalkylphenyl wherein the alkyl is C.sub.1 -C.sub.4,
naphthyl,
anthracenyl,
benzamidocycloalkyl wherein the alkyl is C.sub.1 -C.sub.2,
pyranylmethyl,
tetrahydrofurfuryl,
thiophenemethyl,
benzhydryl,
halobenzhydryl,
polycyclic alcohol, and
substituted phenyl wherein the substituents are selected from the group consisting of:
C.sub.1 -C.sub.4 alkyl,
halogen,
nitro,
trifluoromethyl,
formyl,
chloroacetyl,
C.sub.1 -C.sub.4 alkoxy,
hydrogen,
benzyl,
chlorobenzyl,
phenethyl, and
substituted phenethyl wherein the substituents are selected from the group of:
C.sub.1 -C.sub.4 alkyl and halogen, and
R.sub.11 is selected from the group consisting of:
C.sub.1 -C.sub.4 alkyl,
C.sub.3 -C.sub.6 alkoxyalkyl, and
C.sub.3 -C.sub.4 alkenyl,
R.sub.10 and R.sub.11 taken together form heterocyclic compounds, preferably herterocyclic compounds selected from the group consisting of:
azepinyl, morpholinyl, piperdinyl, C.sub.1 -C.sub.3 alkyl substituted peperdinyl, and
Y is hydrogen or methyl provided that when X=O or S then R.sub.10 is other than hydrogen and substituted phenyl wherein the substituents are selected from the group consisting of:
halogen,
C.sub.1 -C.sub.4 alkoxy,
phenoxy,
trifluoromethyl,
C.sub.1 -C.sub.6 thioalkyl,
nitro,
isocyanato,
C.sub.2 -C.sub.4 polyalkoxy,
C.sub.3 -C.sub.7 cycloalkyl,
C.sub.3 -C.sub.24 carboalkoxyalkyl, preferably C.sub.3 -C.sub.10 carboalkoxyalkyl,
C.sub.1 -C.sub.8 haloalkyl, preferably C.sub.1 -C.sub.4 haloalkyl,
C.sub.3 -C.sub.12 alkenyl, preferably C.sub.3 -C.sub.4 alkenyl,
C.sub.2 -C.sub.6 dialkylamino, phenylamino,
C.sub.1 -C.sub.24 alkyl, preferably C.sub.1 -C.sub.4 alkyl,
C.sub.3 -C.sub.12 hydroxyalkylamidoalkyl,
C.sub.5 -C.sub.10 N,N-hyroxyalkylureidoalkyl,
isocyanatoalkyl wherein the alkyl is C.sub.1 -C.sub.5,
C.sub.3 -C.sub.12 alkylamidoalkyl, polyalkoxyamidoalkyl wherein the polyalkoxy moiety contains from 3-6 repeating C.sub.2 -C.sub.3 alkoxy units and the amidoalkyl moiety contains from 4-12 carbon atoms,
--SO.sub.2 Cl,
--SO.sub.2 polyalkoxyamidoalkyl wherein the polyalkoxy moiety contains from 3-6 repeating C.sub.2 -C.sub.3 alkoxy units and the amidoalkyl moiety contains from 4-12 carbon atoms,
R.sub.5 is selected from the group consisting of: hydrogen,
C.sub.1 -C.sub.4 alkyl,
C.sub.3 -C.sub.6 alkoxyalkyl,
C.sub.3 -C.sub.4 alkenyl,
hydroxyethyl, and
phenyl,
R.sub.4 and R.sub.5 taken together from heterocyclic compounds, preferably heterocyclic compounds selected from the group consisting of:
azepinyl,
morpholinyl,
piperdinyl, and
C.sub.1 -C.sub.3 alkyl substituted piperdinyl, ##STR20## wherein X is O or S, n is 0 or 1, R.sub.6 is selected from the group consisting of:
C.sub.1 -C.sub.18 alkyl, preferably C.sub.1 -C.sub.12 alkyl, more preferably C.sub.1 -C.sub.4 alkyl,
C.sub.2 -C.sub.6 haloalkyl, phenyl, and substituted phenyl wherein when N =1 the substituents are selected from the group consisting of:
nitro,
chloro,
C.sub.1 -C.sub.2 alkyl,
C.sub.4 -C.sub.6 polyalkoxyalkyl,
C.sub.3 -C.sub.8 cycloalkyl,
C.sub.3 -C.sub.4 alkenyl,
C.sub.3 -C.sub.6 alkoxyalkyl,
C.sub.2 -C.sub.6 hydroxyalkyl,
C.sub.1 -C.sub.3 carboxyalkyl, and
C.sub.5 -C.sub.8 trialkylammoniumalkyl salts,
and when n=0 the substituents are selected from the group consisting of:
chloro,
thiopotassium,
C.sub.1 -C.sub.18 alkyl, preferably C.sub.1 -C.sub.12 alkyl, more preferably C.sub.1 -C.sub.4 alkyl,
benzyl,
C.sub.1 -C.sub.2 heteroalkyl,
C.sub.2 -C.sub.4 chlorocarboxyalkyl,
C.sub.4 -C.sub.6 polyalkoxyalkyl, and
acetyl, ##STR21## wherein R.sub.7 is selected from the group consisting of: --(CH.sub.2 --).sub.n wherein n=0 to 8, --CH.dbd.CH--, ##STR22## wherein M is H or Cl, ##STR23## --CCl.dbd.CCl--, --CH.sub.2 OCH.sub.2 --, and
--OCH.sub.2 CH.sub.2 O--, and
d=0 or 1, and when d=1
Y is selected from the group consisting of:
--O,
--S, and
--NH,
Z is selected from the group consisting of:
C.sub.1 -C.sub.18 alkyl, preferably
C.sub.1 -C.sub.12 alkyl, more preferably C.sub.1 -C.sub.4 alkyl,
hydrogen,
C.sub.4 -C.sub.16 polyalkoxyalkyl,
C.sub.4 -C.sub.8 dialkylaminoalkyl,
C.sub.3 -C.sub.5 alkynyl,
phenyl,
substituted phenyl,
organic salts,
inorganic salts, and
when d=0, Z is Cl or ##STR24## wherein R, R.sub.1 and R.sub.2 are as defined above, ##STR25## wherein R.sub.8 is selected from the group consisting of: C.sub.1 -C.sub.10 alkoxy, preferably C.sub.1 -C.sub.5 alkoxy,
amino,
C.sub.1 -C.sub.10 alkoxyamino, preferably C.sub.1 -C.sub.5 alkoxyamino,
hydroxy, and
organic base
--SO.sub.w R.sub.9 wherein w=0-2 and R.sub.9 is selected from the group consisting of:
amino,
C.sub.1 -C.sub.10 alkyl, preferably C.sub.1 -C.sub.5 alkyl,
C.sub.1 -C.sub.4 haloalkyl, phenyl,
C.sub.1 -C.sub.10 dialkylamino,
C.sub.1 -C.sub.10 alkylamino,
C.sub.1 -C.sub.10 alkoxy, preferably C.sub.1 -C.sub.5 alkoxy,
substituted phenyl wherein the substituents are selected from the group consisting of:
nitro,
chloro,
C.sub.1 -C.sub.4 alkyl; and methoxy.
GENERAL METHODS OF PREPARATION
The compounds of the present invention are derivatives of isothioureas containing one free hydrogen atom attached to nitrogen, that is, as shown by the following formula: ##STR26## The formation of the prior art isothioureas is well known in the art. They are derived by the reaction of an isothiocyanate with a primary amine to form a thiourea followed by the reaction with an alkyl halide to produce an isothiourea salt. An unreactive solvent such as ethanol can be used for both the formation of the thiourea and the alkylation step to form the isothiourea salt. Heat is usually used to speed both reactions. The preparation of the isothiourea salt is shown below: ##STR27##
The compounds of this invention are prepared by reacting the base of an isothiourea with an isocyanate or acid chloride. The free base can either be prepared by neutralization of an isothiourea salt with a cold aqueous solution of a base such as dilute sodium hydroxide, extracting the free isothiourea with a water insoluble solvent such as hexane, benzene, toluene, etc., drying over a dehydrating agent such as magnesium sulfate, filtering and evaporation under vacuum. An alternative procedure is to dissolve the isothiourea salt in a non-reactive solvent such as benzene or toluene then adding an equal molar amount of an isocyanate and the equivalent amount of a soluble tertiary base or an acid chloride and two equivalent amounts of a soluble tertiary base such as triethylamine, completing the reaction by stirring at ambient temperature for several hours or refluxing for a shorter period of time. An alternative method when using a base such as triethylamine is to treat the isothiourea salt in a solvent such as benzene in which triethylamine hydrohalide is almost totally insoluble, filtering off the triethylamine hydrohalide and treating the filtrate with the isocyanate or acid chloride, completing the reaction as discussed previously. Solvents suitable for the condensation of the isothiourea with an isocyanate or acid chloride are those which are unreactive to any of the reactants. These include hexane, benzene, toluene, tetrahydrofuran, dioxane, methylenechloride, diethylether, and the like. Depending on the reactants, reaction temperatures are generally within the range of -20.degree. C. to 80.degree. C. and reaction times vary from 0.5 hours to 24 hours.
In some instances, it has been found that the condensation of an isothiourea with an isocyanate or acid chloride can be hastened by the addition of such catalysts as triethylamine and dibutyltindilaurate.
Equations showing the reactions just discussed are as follows:
(A) Using isothiourea base with an isocyanate ##STR28##
(B) Using isothiourea salt+a base ##STR29##
(C) Using isothiourea base with an acid chloride ##STR30##
The isothiourea precursors of the prior art discussed above can in general be prepared by the methods disclosed in U.S. Pat. Nos. 3,969,511 and 4,062,892.
These compounds are useful as lepidoptericides when used in a lepidoptericidally effective amount on insects of the order lepidoptera or their habitat or feedstuffs. Some of the compounds also show phytotoxic effects which could render them useful as herbicides as well as lepidoptericides if such efficacy was desired. In addition, some of these compounds show biocidal and/or fungicidal effects.
By "lepidoptericidally effective amount" is meant the amount of the herein disclosed lepidoptericidal compounds which when applied in any conventional manner to the habitat of the lepidoptera, the feedstuffs of lepidoptera, or the insects themselves, will "control" by killing or substantially injuring a significant portion of the lepidoptera.
These compounds are useful in protecting food, fiber forage crops and ornamental crops from damage by insects and larva of other order lepidoptera. Examples of crops to be protected include forest trees such as oak and pine, fruit trees such as peach, apple and walnut, vegetables such as tomatoes, other crops such as tobacco, cotton, lettuce, cabbage, corn and rice and any crop which lepidoptera feed upon.
The novel compounds of this present invention can be prepared from the above precursors by methods shown in the following examples.

EXAMPLE 1
1,3-Diheptyl-2-ethyl-3-(O,O-dimethyl phosphoro)isothiourea
6.0 grams (g) (0.02 mole) of 1,3-diheptyl-2-ethyl isothiourea and 200 milliliters (ml) of methylene chloride were combined in a 500 ml 3-neck flask fitted with a carrier, thermometer and dropping funnel. The solution was stirred and cooled to 0.degree. C. 2.0 g (0.02 mole) of triethylamine was added to the flask. Next, 3.0 g (0.02 mole) of phosphorus oxychloride dissolved in 25 ml of methylene chloride was added at such a rate that the pot temperature was maintained at 0.degree. to 5.degree. C. After the addition was complete, the reaction mass was stirred at 0.degree. C. for 30 minutes. Then, a solution of 8.7 g (0.04 mole) of 25 percent sodium methoxide in methanol with 25 ml of methylenechloride was added over a period of 15 minutes while the pot temperature was maintained at 0.degree. to 5.degree. C. The reaction mass was then stirred at 5.degree. C. for 30 minutes and then at room temperature for 30 minutes. The resulting mixture was then washed with two 200 ml portions of water and phase separated. The methylene chloride phase was dried with anhydrous MgSO.sub.4, filtered and evaporated invacuo to yield 7.4 g of the desired product, 1,3-diheptyl-2-ethyl-3-(O,O-dimethylphosphoro)isothiourea which had a n.sub.D.sup.30 of 1.4528. The product identification was confirmed by infrared (IR), H-nuclear magnetic resonance (NMR) and C.sup.13 -NMR spectra. Compound No. 229 in Table I.
EXAMPLE 2
1,3-diheptyl-2-ethyl-3-N-[4-methyl-3-(carbowax-350-carbamyl)]phenyl carbamyl isothiourea
The title compound was formed as follows:
Intermediate (a)
3.56 g (0.02 mole) of 2-methyl-5-nitrophenylisocyanate, 7.0 g (0.02 mole) of carbowax 350, 2 drops of triethylamine, 1 drop of di-butyltindilaurate and 25 ml of methylene chloride were combined with stirring in a 100 ml round bottom flask. After the exotherm had subsided, the solvent was removed invacuo. The residue was dissolved in a 10:1 mixture of diethylether-toluene. A white solid impurity was removed by filtration and evaporation of the filtrate invacuo gave 10.5 g of the desired compound N-(2-methyl-5-nitrophenyl) carbowax (350) carbamate, n.sub.D.sup.20 1.4810. The structure was confirmed by C.sup.13 -NMR spectra.
Intermediate (b)
7 g (0.013 mole) of intermediate (a) was dissolved in 200 ml of ethanol in a Parr glass pressure bottle. 1 g of palladium on carbon catalyst was added and the mixture was shaken and reacted with hydrogen maintained at a pressure of 50 psi for 30 minutes. The reaction mass was then filtered and the filtrate was evaporated invacuo to yield 6.0 g of the desired compound N-(2-methyl-5-aminophenyl) carbowax (350) carbamate. The structure was confirmed by C.sup.13 -NMR spectra.
Intermediate (c)
5.8 g (0.0116 mole) of intermediate (b) was dissolved in 200 ml of toluene in a 250 ml 3-neck flask fitted with a condenser, stirrer and gas inlet tube. The solution was stirred, heated to 70.degree. C. and saturated with HCl gas. The mixture was then heated to reflux and phosgene was bubbled in for 30 minutes. The reaction mass became clear. N.sub.2 gas was then bubbled in to remove the excess phosgene. The solvent was removed invacuo to yield 6.1 g of N-(2-methyl-5-isocyanophenyl) carbowax (350) carbamate, n.sub.D.sup.30 1.5848. The structure was confirmed by C.sup.13 -NMR spectra.
1,3-diheptyl-2-ethyl-3-N-[4-methyl-3-(carbowax-350-carbamyl)]phenyl carbamyl isothiourea
2.0 g (0.004 mole) of intermediate (c), 1.2 g (0.004 mole) of 1,3-diheptyl-2-ethylisothiourea, 2 drops of triethylamine and 15 ml of methylene chloride were combined in a 100 ml round bottom flask. After the exotherm had subsided, the solvent was removed invacuo to yield 3.3 g of the desired product, 1,3-diheptyl-2-ethyl-3-N-[4-methyl-3-(carbowax-350-carbamyl)phenyl carbamyl]isothiourea. The structure was confirmed by C.sup.13 -NMR spectra. Compound No. 216 in Table I.
EXAMPLE 3
1,3-diheptyl-2-ethyl-3-[N-(3-tergitol(15-S-7)oxycarbamylphenyl)carbamyl]isothiourea
The title compound was formed as follows:
Intermediate (d)
In the same manner as intermediate (a) of Example 2 above, 3.28 g (0.02 mole) of 3-nitrophenylisocyanate, 10.1 g of tergitol (15-S-7), 2 drops of triethylamine and 25 ml of methylene chloride were combined to yield 13.2 g of the desired compound, N-(3-nitrophenyl)tergitol(15-S-7)carbamate. Structure was confirmed by IR spectra.
Intermediate (e)
In the same manner as intermediate (b) of Example 2 above, 11.2 g (0.0166 mole) of intermediate (d) was reduced with H.sub.2 in ethanol using 1 g of palladium on carbon catalyst to yield 9.3 g of the desired compound, N-(3-aminophenyl)tergitol(15-S-7)carbamate. Structure was confirmed by IR spectra.
Intermediate (f)
In the same manner as intermediate (c) of Example 2 above, 9.3 g (0.0145 mole) of intermediate (e) was treated with excess HCl gas followed by excess phosgene to yield 9.4 g of the desired compound, N-(3-isocyanophenyl)tergitol(15-S-7)carbamate. Structure was confirmed by IR spectra.
1,3-diheptyl-2-ethyl-3-[N-(3-tergitol(15-S-7)oxycarbamylphenyl)carbamyl]isothiourea
In the same manner as the title compound of Example 2 above, was prepared 2 g (0.003 mole) of intermediate (f) was combined with 0.9 g (0.003 mole) of 1,3-diheptyl-2-ethylisothiourea, 2 drops of triethylamine and 10 ml of methylene chloride to yield 2.9 g of the desired product, 1,3-diheptyl-2-ethyl-3-[N-(3-tergitol(15-S-7)oxycarbamylphenyl)carbamyl]isothiourea n.sub.D.sup.30 1.5710. Structure was confirmed by IR spectra. Compound No. 219 in Table I.
EXAMPLE 4
1,3-diheptyl-2-ethyl-3-(O,O-diethylphosphorodithioyl acetytl)isothiourea
Intermediate (g)
30 g (0.1 mole) of 1,3-diheptyl-2-ethylisothiourea, 12.4 g (0.11 mole) of chloroacetylchloride and 250 ml of toluene were combined in a 500 ml 3-neck flask fitted with a stirrer, thermometer and dropping funnel. The solution was stirred and cooled to -30.degree. C. with a dry-ice bath. 11.1 g (0.11 mole) of triethylamine was then added over a period of 30 minutes. After the addition was complete, the reaction mass was allowed to warm to room temperature and stirring was continued for 1 hour. The reaction mass was then washed in turn with two 200 ml portions of water, 100 ml of saturated sodium bicarbonate solution and finally with two 200 ml portions of water. The toluene phase was dried with anhydrous MgSO.sub.4, filtered and evaporated invacuo to yield 36.1 g of the desired compound, 1,3-diheptyl-2-ethyl-3-chloroacetylisothiourea. The structure was confirmed by IR and NMR spectra.
1,3-diheptyl-2-ethyl-3-(O,O-diethylphosiphorodithioyl acetyl isothiourea
2.2 g (0.012 mole) of O,O-diethyldithiophosphoric acid was dissolved in 25 ml of acetone and was treated with 5 g of anhydrous potassium carbonate. After neutralization, the acetone phase was decanted into a 250 ml flask containing a solution of 3.0 g (0.008 mole) of intermediate (g) in 75 ml of acetone. The resulting mixture was stirred at room temperature for 2 hours, then was poured into two 200 ml of toluene. The resulting mixture was washed with two 200 ml portions of water. The toluene phase was then dried with anhydrous MgSO.sub.4, filtered and evaporated invacuo to yield 3.6 g of the desired product, 1,3-diheptyl-2-ethyl-3-(O,O-diethylphosphorodithioylacetyl)isothiourea. n.sub.D.sup.30 1.5060. The structure was confirmed by IR and NMR spectra. Compound No. 261 in Table I.
EXAMPLE 5
N,N'-diheptyl-S-ethyl-N-propane sulfonyl isothiourea
1.8 g (0.018 mole) of triethylamine was added to 4.5 g (0.015 mole) N,N'-diheptyl-S-ethyl-isothiourea in 50 ml methylene chloride in a stirred round bottom flask. A solution of propanesulfonyl chloride (0.018 mole, 2.6 g) in 8 ml methylene chloride was added dropwise to the above solution at 0.degree. C. The mixture was stirred 1.5 hours at room temperature then at 30.degree.-35.degree. C. for 1.5 hours. The cooled solution was washed twice with 20 ml water, once with 25 ml saturated sodium bicarbonate solution and twice more with 20 ml of water. The organic phase was dried over magnesium sulfate and evaporated invacuo to yield the product as a yellow oil. n.sub.D.sup.30 1.4805. Yield was 5.2 g (85.4% of theory). The structure was confirmed by IR spectrum. Compound No. 203 in Table I.
EXAMPLE 6
N,N'-diheptyl-S-ethyl-N'-p-toluene sulfonyl isothiourea
The reaction was carried out with 0.018 mole (3.4 g) p-toluenesulfonyl chloride in the same manner as Example 5 above. The product had a n.sub.D.sup.30 of 1.517. Yield was 6.0 g (88% of theory). IR, NMR spectra and mass spectroscopy confirmed the structure. Compound No. 206 in Table I.
EXAMPLE 7
1,3-di-n-heptyl-1-trichloromethylthio-2-ethyl isothiourea
3 g (0.01 mole) 1,3-di-n-heptyl-2-ethyl isothiourea was mixed with 50 ml tetrahydrofuran in a stirred round bottom flask and cooled in an ice bath. 1.4 ml (0.01 mole) triethylamine was added and the mixture stirred for 10 minutes. 1.1 ml (0.01 mole) trichloromethyl sulfenyl chloride was added to the mixture dropwise over 2 minutes. A white precipitate formed and the mixture was stirred for 1 hour while coming to ambient temperature. The resultant reaction mixture was allowed to sit overnight. The mixture was suction filtered to remove the white solid which was rinsed twice with 10 ml of fresh tetrahydrofuran. The filtrate was evaporated under vacuum resulting in 4.55 g of the title product at a yield of 101.2 percent. The resulting liquid had a n.sub.D.sup.30 of 1.5084 and was identified as the title compound by IR spectrum and mass spectroscopy. Compound No. 297 in Table I.
EXAMPLE 8
1,3-di-n-heptyl-1-(2'-fluoro-1',1',2',2'-tetrachloroethylthio-2-ethylisothiourea
2.0 g (0.007 mole) 1,3-di-n-heptyl-2-ethyl isothiourea was dissolved in 100 ml tetrahydrofuran and placed in a stirred round bottom flask and placed in an ice bath. 0.7 g (0.0069 mole) triethylamine was added and the mixture stirred for 10 minutes. 1.68 g (0.0068 mole) 2-fluoro-1,1,2,2-tetrachloroethylsulfenyl chloride dissolved in 20 ml of tetrahydrofuran was added over approximately 15 minutes. A precipitate formed while the mixture was stirred for 2 hours. The mixture was suction filtered and the precipitate was washed twice with 20 ml tetrahydrofuran. The filtrate was vacuum evaporated. The title product's yield was 3.53 g of a liquid having a n.sub.D.sup.30 of 1.5091. The product identity was confirmed by IR spectrum and mass spectroscopy. Compound No. 298 in Table I.
EXAMPLE 9
1,3-di-n-heptyl-1-o-nitrophenylthio-2-ethylisothiourea
1.9 g (0.01 mole) of 2-nitro benzene sulfenyl chloride was dissolved in 50 ml of tetrahydrofuran. A mixture of 3 g (0.01 mole) 1,3-di-n-heptyl-2-ethylisothiourea in 30 ml of tetrahydrofuran was added to the mixture in a glass round bottom stirred flask cooled in an ice bath. 1.05 g (0.01 mole) of triethylamine in 10 ml of tetrahydrofuran was added over a period of 10 minutes. A white precipitate formed immediately and the reaction mixture was stirred in the bath for 3 hours while coming to ambient temperature and then suction filtered. The filtrate was vacuum evaporated to produce a light brown sticky residue which was redissolved in approximately 100 ml diethyl ether and filtered through magnesium sulfate and Dicalite 4200 by suction. The filtrate was vacuum stripped to produce 4.2 g of a liquid having a n.sub.D.sup.30 of 1.5463. The product was identified as the title product by IR spectrum. Compound No. 300 in Table I.
EXAMPLE 10
S-ethyl-1,3-diheptyl-3-(2-carboethoxy)ethyl-2-isothiourea
3 g (0.01 mole) of S-ethyl-1,3-diheptyl-2-isothiourea and 3 g (0.03 mole) of ethyl acrylate were placed in a 100 ml glass flask. A catalytic amount of base (0.1 g NaH) was added and the mixture heated from 25.degree. to 85.degree. C. and held at 85.degree. C. for 5 hours. The reaction mixture was cooled and 150 ml of ether was added. The ether was washed with 100 ml of water, then dried and stripped to yield 2 g of the title product. The structure was verified by IR and NMR spectra. Compound No. 199 in Table I.
EXAMPLE 11
S-ethyl-1,3-diheptyl-3-(3-oxobutyl)-2-isothiourea
The procedure was the same as for Example 10 except ethyl acrylate was replaced with methyl vinyl ketone and the reaction was run at room temperature for 4 hours. Work-up of the product was the same. 2 g of the title product was produced and identified by IR and NMR spectra. Compound No. 200 in Table I.
EXAMPLE 12
N,N-di-n-heptyl-N'-ethyloxalyl-S-ethyl-isothiourea
5.0 g (16.6 millimoles) of S-ethyl-1,3-diheptyl-2-isothiourea and 1.8 g (18.3 millimoles) of triethylamine in 50 ml of methylene chloride were mixed together in a 100 ml single necked round bottom flask equipped with a magnetic stirrer and stopper. The clear light yellow solution was cooled to 0.degree. C. in an ice bath. To this stirred, cooled solution was added 2.50 g (18.3 millimoles) of ethyloxalyl chloride dropwise while maintaining the temperature between 5.degree. to 15.degree. C. A large amount of a white precipitate formed within seconds and stirring was allowed to continue for 1 hour at 0.degree. C. The cooling bath was removed and the mixture stirred at room temperature for 3 hours. The precipitate was dissolved by the addition of 50 ml water and the mixture transferred to a separatory funnel containing 50 ml of methylene chloride. The layers were separated and the organic phase washed once with 10 ml of saturated NaHCO.sub.3, 3 times with 10 ml portions of water, once with 10 ml of saturated sodium chloride and dried over Na.sub.2 SO.sub.4. The dried, clear yellow organic solution was filtered through Na.sub.2 SO.sub.4 and the solvent was removed under vacuum to yield 6.63 g (99.7% yield) of the title product as a clear, yellow oil having a n.sub.D.sup.30 of 1.4757. The product was identified as the title product by IR and NMR spectra and mass spectroscopy. Compound No. 671 in Table I.
EXAMPLE 13
Bis-N'-(N,N'-n-heptyl-S-ethylisothioureyl)-oxalate
The procedure for Example 13 is the same as for Example 12 above with the exception that a 200 ml single necked round bottom flask was used in place of the 100 ml flask and 1.16 g (9.13 millimoles) of oxalyl chloride was substituted for the ethyloxalyl chloride of the previous example. The reaction resulted in a clear yellow solution which was stirred at 0.degree. C. for 1 hour and then stirred at room temperature for 20 hours. The clear yellow solution was then transferred to a separatory funnel containing 50 ml of water and 50 ml of methylene chloride. The layers were phase separated and the organic phase washed once with 10 ml of 10 percent potassium carbonate, 5 times with 10 ml portions of water, once with 10 ml of saturated sodium chloride and dried over Na.sub.2 SO.sub.4. The dried organic solution was filtered and the solvent removed as in Example 12 to yield 5.55 g (102.1% of theory yield) of an orange oil having a n.sub.D.sup.30 of 1.4932. The product was identified as the title product by IR and NMR spectra and mass spectroscopy. Compound No. 688 in Table I.
EXAMPLE 14
N,N'-Di-(1-heptyl)-N'-(ethylmercapto carbonyl)-S-ethyl isothiourea
The procedure and equipment were the same as in Example 12 above with the exception that 5.0 g (16.6 millimoles) of N,N'-di-(1-heptyl)-S-ethyl isothiourea and 1.85 g (18.3 millimoles) of triethylamine and 50 ml of methylene chloride were added to the flask followed by addition of 2.28 g (18.3 millimoles) of ethylthio chloroformate. The resultant product was phase separated, washed and dried in a manner of Example 12. The solvent was removed under vacuum to yield 6.55 g (101.5% of theory yield) of accrued yellow oil having a n.sub.D.sup.30 of 1.4922. The product was identified as the title product by IR and NMR spectra and mass spectroscopy. Compound No. 300 in Table I.
EXAMPLE 15
1,3-diheptyl-2-ethyl-3-[3'-2"-ethoxyethoxycarbonylamino)-4'-methylphenylaminocarbonyl)isothiourea
The title product was prepared as follows:
Step (a) 1,3-diheptyl-2-ethyl-3-(3-isocyanato-4-methylphenylaminocarbonyl)isothiourea (Intermediate).
125 cubic centimeters (cc) of methylene chloride was pipetted under argon flow into a 200 cc 3-neck stirred flask, 15.1 g (0.86 mole) of toluene-2,4-diisocyanate was then added to the methylene chloride. Next, 25.8 g (0.086 mole) of 1,3-diheptyl-2-ethyl isothiourea was added without cooling over a period of 5 minutes. The temperature increased from 20 to approximately 30.degree. C. during this addition. The reaction mixture was then heated to reflux (41.degree. C.) and held at reflux temperature for 1 hour. The resultant reaction mixture was then concentrated on a rotary evaporator under high vacuum. The reaction produced 39.8 g of product having a n.sub.D.sup.30 of 1.5318 which was identified as the intermediate title product by IR and carbon 13 NMR spectra.
Step (b) Preparation of 1,3-diheptyl-2-ethyl-3-[3'-(2"ethoxyethoxycarbonylamino)-4'-methylphenylaminocarbonyl]isothiourea.
4.74 g (0.010 mole) of the intermediate of step (a) 0.95 g (0.0105 mole) 2-ethoxyethanol, 2 drops of triethylamine, 1 drop of dibutyltindilaurate and 25 cc of tetrahydrofuran dried over a Linde Molecular Sieve 3A were charged to a 3-neck flask. The mixture was brought to reflux (67.degree. to 68.degree. C.) and held at reflux for 2 hours. The solvent was then removed under high vacuum at a pressure of 0.3 mm or less and at a bath temperature of 80.degree. to 90.degree. C. 5.6 g of a viscous oil was recovered and identified as the title product by IR and carbon 13 NMR spectra analyses. Compound No. 419 in Table I.
EXAMPLE 16
1,3-diheptyl-2-ethyl-3-[3'-(3"-chloro-4"-methylphenylureido)-4'-methylphenylaminocarbonyl]isothiourea
The reaction and reactants were identical to the reaction of Example 15(b) with the exception that 1.49 g (0.0105 mole) of 3-chloro-4-methylaniline is substituted for the 2-ethoxyethanol. An insoluble by-product was formed which was removed by filtering before evaporation of the solvent. The reaction produced 3.5 g of a product identified as the title product by IR and NMR spectra analyses. Compound No. 429 in Table I.
EXAMPLE 17
1,3-diheptyl-2-ethyl-3-[3'-propylureido-4'-methylphenylaminocarbonyl]isothiourea
4.74 g (0.010 mole) of the intermediate as prepared in Example 15(a) and 25 cc of dry tetrahydrofuran were charged to a 3-neck flask. 0.62 g (0.0105 mole) of propylamine was added at room temperature without cooling. The reaction was exothermic and the temperature rose about 10.degree. to 20.degree. C. No heat was applied to the mixture and the reaction was completed in 1 hour. The mixture was filtered from a small amount of solid by-product and was worked up in the manner of Example 15(b). The reaction produced 5.0 g of a liquid having a n.sub.D.sup.30 of 1.5312 and was identified as the title product by IR and carbon 13 NMR spectra analyses. Compound No. 431 in Table I.
EXAMPLE 18
1,3-diheptyl-2-ethyl-3[3'-p-chlorobenzylthiocarbonylamino-4'-methylphenylaminocarbonyl]isothiourea
The reactants were the same as in Example 15(b) with the exception that 1.66 g (0.0105 mole) of 4-chlorobenzylmercaptan was substituted for the 2-ethoxyethanol. The reaction produced 6.5 g of a viscous liquid which was identified as the title product by IR and NMR spectra analyses. Compound No. 433 in Table I.
EXAMPLE 19
1,3-diheptyl-2-ethyl-3-(3'-phenoxycarbonylamino-4'-methylphenylaminocarbonyl)isothiourea
The reactants were the same as in Example 15(b) with the exception that 0.99 g (0.0105 mole) of phenol was substituted for the 2-ethoxyethanol. The reaction produced 5.2 g of a liquid having a n.sub.D.sup.30 of 1.5488 which was identified as the title product by NMR and IR spectra analyses. Compound No. 452 in Table I.
EXAMPLE 20
1-octyl-2-ethyl-3-sec-heptyl-3-[3-(1-octyl-2-propyl-3-sec-heptyl-3-carbonylamino)-4-methylphenylcarbonylamino]isothiourea
Step (a) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3-(3-isocyanato-4-methylphenylaminocarbonyl)isothiourea (Intermediate).
This intermediate was prepared as was the intermediate of Example 15(a) with the exception that 27.2 g (0.086 mole) of 1-octyl-2-ethyl-3-sec-heptylisothiourea was substituted for the thiourea reactant of step 25(a). The reaction produced 41.5 g (98.8 weight percent of theory) of a liquid having a n.sub.D.sup.30 of 1.5280 which identified as the title intermediate by IR and carbon 13 NMR spectra analyses.
Step (b) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3-[3-(1-octyl-2-propyl-3-sec-heptyl-3-carbonylamino)-4-methylphenylcarbonylamino]isothiourea.
The title product was prepared in the manner of step 15(b) with the exception of using 4.87 g (0.010 mole) of the intermediate prepared in step 20(a) and 3.29 g (0.010 mole) of 1-octyl-2-propyl-3-sec-heptyl isothiourea. The reaction produced 7.9 g (96.3 weight percent of theory) of a liquid having a n.sub.D.sup.30 of 1.5185 which was identified as the title product by IR and carbon 13 NMR spectra analyses. Compound No. 558 in Table I.
EXAMPLE 21
1,3-bis-n-heptyl-1-(carbamylsulfonylchloride)-2-S-ethyl isothiourea
50 ml of dry methylene chloride and 8.49 g of chlorosulfonyl isocyanate (aldrich) were placed in a 200 ml flask provided with a magnetic stirrer, thermometer and dropping funnel. A solution of 18 g of the 1,3-diheptyl-2-ethyl isothiourea (in 100 ml dry methylene chloride) was added dropwise over 40-45 minutes. The reaction exhibited a slight exotherm so the flask was cooled in a water bath to hold the temperature below 28.degree. C. The solution was then stirred at about 25.degree. C. overnight.
The solution was then filtered and the filtrate concentrated under reduced pressure. 26.2 g (99 weight percent of theory) of a thick liquid having a n.sub.D.sup.30 of 1.4833 was recovered. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 635 in Table I.
EXAMPLE 22
1,3-bis-n-heptyl-1-chlorocarbonyl-2-ethyl isothiourea
100 ml of dry CH.sub.2 Cl.sub.2 was placed in a 500 ml flask equipped with a thermometer and dropping funnel and cooled to 5.degree. C. in an ice bath. A solution of phosgene in benzene (170 g of 17.5 percent weight concentration) was then added. Next, a solution of 100 ml of dry CH.sub.2 Cl.sub.2, 10.1 g triethylamine and 30 g of 1,3-diheptyl-2-ethyl isothiourea was added dropwise over a one hour period at 5.degree. C. The mixture was then stirred overnight at ambient temperature.
The next morning the reaction mixture was warmed to about 40.degree. C. for 21/2-3 hours to ensure completion of the reaction. The mixture was then subjected to reduced pressure to remove the CH.sub.2 Cl.sub.2 solvent. 100 ml of dry ether was added and the mixture filtered by suction on a glass frit. The solid was washed by a little more ether and the combined filtrates concentrated under reduced pressure to remove the ether. 38.6 g of a liquid (106 weight percent of theory) having a n.sub.D.sup.30 of 1.4613 was recovered. The product was identified as the title product by mass spectra analyses. Compound No. 643 in Table I.
EXAMPLE 23
1,3-bis-n-heptyl-1-diethylcarbamyl-2-ethyl isothiourea
100 ml of dry benzene and 5.44 g of 1,3-diheptyl-2-ethyl isothiourea carbamyl chloride were placed in a 200 ml flask equipped with a thermometer and dropping funnel. A solution of 12 ml dry benzene and 2.19 g diethyl amine was added dropwise over 10-12 minutes. An exotherm raised the temperature from 21.degree. to 30.degree. C. The mixture was then heated to 45.degree.-50.degree. C. for 3 hours. The reaction mixture was then cooled to 15.degree. C. and washed twice by 50 ml portions of cold water. The benzene phase was dried by MgSO.sub.4, filtered and the solvent removed under reduced pressure. 5.75 g of a liquid (96 weight percent of theory) having a n.sub.D.sup.30 of 1.4568 was recovered. The structure was confirmed as the title compound by mass spectra analyses. Compound No. 644 in Table I.
EXAMPLE 24
1,3-bis-n-heptyl-1-(propargyloxycarbonyl)-2-ethyl isothiourea
50 ml of dry tetrahydrofuran and 0.36 g of NaH were placed in a 200 ml flask equipped with a thermometer and dropping funnel. A solution of 10 ml dry THF and 0.84 g propargyl alcohol was added dropwise over 8-10 minutes. The reaction mixture liberated hydrogen and exhibited a slight exotherm. The mixture was then stirred for 3 hours to complete the reaction.
Then a solution of 15 ml dry THF and 5.44 g of the 1,3-diheptyl-2-ethyl isothiourea carbamyl chloride was added dropwise over 10 minutes. The mixture was stirred and warmed to 45.degree. C. for 2 hours. The reaction was cooled to 25.degree. C. and filtered by suction on a glass frit and filter. The solvent was removed under reduced pressure. 5.0 g of a liquid (88 weight percent of theory) having a n.sub.D.sup.30 of 1.4553 was recovered. The structure was confirmed as the title compound by NMR and spectra analyses. Compound No. 648 in Table I.
EXAMPLE 25
1,3-bis(2-ethylhexyl)-1-(succinic anhydride adduct)2-ethylisothiourea.Et.sub.3 N salt
200 ml of dry CH.sub.2 Cl.sub.2, 32.8 g of 1,3-(2-ethylhexyl)-2-ethyl isothiourea, 11 g of succinic anhydride and 11.1 g of Et.sub.3 N were placed in a 500 ml flask. There was a slight exotherm upon mixing these components. The solution stood overnight.
The reaction mixture was then stripped under reduced pressure. 47.3 g of a liquid (89 weight percent of theory) having a n.sub.D.sup.30 of 1.4899 was recovered. The structure was confirmed as the title compound by IR and NMR spectra analyses. Compound No. 665 in Table I.
EXAMPLE 26
Reaction product of 2 moles of 1,3-di-(2'-ethylhexyl)-2-S-ethyl isothiourea+toluene-2,4-diisocyanate
In a three-neck 200 ml flask equipped with a magnetic stirrer, 3.28 g (0.01 mole) of 1,3-di-(2'-ethylhexyl-2-S-ethyl isothiourea was mixed with 20 ml of tetrahydrofuran. To this solution was added 0.87 g (0.005 mole) of toluene-2,4-diisocyanate. The temperature rose from 23.degree. C. to 34.degree. C. The mixture was allowed to stand at ambient temperature overnight after which it was evaporated under vacuum. Infrared analysis showed that the reaction was incomplete, therefore, the mixture was dissolved in 30 ml of methylenechloride and 1 drop of dibutyltindilaurate and 2 drops of triethylamine were added. The homogenous solution was stirred at ambient temperature for 1.5 hours. The mixture was reevaporated under vacuum to obtain the product as a viscous yellow liquid having a n.sub.D.sup.30 of 1.5201. The yield was 4.3 g. The product was identified as the title compound by both IR and NMR spectra analyses. Compound No. 85 in Table I.
EXAMPLE 27
1,3-di-n-heptyl-1-N-phenylcarbamyl-2-S-n-propyl isothiourea
The equipment was as in Example 26 above. 6.2 g (0.014 mole) 1,3-di-n-heptyl-2-S-n-propyl isothiuronium.hydrogen iodide was dissolved in 35 ml of tetrahydrofuran and 1.68 g (0.014 mole) phenyl isocyanate was added followed by a portion-wise addition of 1.43 g (0.014 mole) triethylamine with cooling. A solid precipitate formed on addition of the triethylamine. The reaction was stirred at ambient temperature overnight. The reaction mixture was then vacuum evaporated to remove tetrahydrofuran and the residue was dissolved in chloroform and washed two times with 150 ml portions of water. The organic phase was then dried over magnesium sulfate, filtered and vacuum evaporated to remove the chloroform. The product was 5.9 g (96.7 weight percent of theory yield) of a yellow liquid having a n.sub.D.sup.30 of 1.5188. The product was identified as the title compound by IR and NMR spectra analyses. Compound No. 11 in Table I.
EXAMPLE 28
1,3-di-n-heptyl-1-N-octadecylcarbamyl-2-S-ethyl isothiourea
The equipment was the same as in Example 26 above. 4.5 g (0.015 mole) 1,3-di-n-heptyl-2-S-ethyl-isothiourea was mixed with 40 ml tetrahydrofuran and 4.43 g (0.015 mole) N-octadecylisocyanate was added. Three drops of triethylamine were added and the mixture stood overnight. The mixture was then warmed to 40.degree. C. for 20 minutes to complete the reaction. A small amount of solid formed on cooling and was filtered off. The reaction mixture was then vacuum evaporated to produce 8.9 g (100 percent of theory yield) of a pale liquid having a n.sub.D.sup.30 of 1.4750. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 29 in Table I.
EXAMPLE 29
1,3-di-n-heptyl-1-N-4-methylthiophenylcarbamyl-2-S-ethyl isothiourea
The equipment was the same as in Example 26 above. 3.0 g (0.01 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 25 ml of methylene chloride. Two drops of triethylamine and 1 drop of dibutyltindilaurate were added and then 1.65 g (0.01 mole) 4-methyl thiophenyl isocyanate was added. The temperature rose from 23.degree. to 33.degree.. The reaction mixture was then vacuum evaporated to remove the methylene chloride to produce 4.65 g (100 percent of theory yield) of a yellow liquid having a n.sub.D.sup.30 of 1.5340. The liquid solidified on standing into a semi-solid. The product was identified as the title product by IR and NMR spectra analyses. Compound No. in Table 47 in Table I.
EXAMPLE 30
1,3-di-n-heptyl-1-N-2-chloroethylcarbamyl-2-S-ethyl isothiourea
The procedure, equipment and reactants were the same as in Example 29 with the exception that 1.06 g (0.01 mole) of 2-chloroethylisocyanate was substituted for the 4-methylthiolphenyl isocyanate. The reaction produced 4.14 g (102 weight percent of theory yield) of a clear liquid having a n.sub.D.sup.30 of 1.4930. The product was confirmed as the title compound by IR and NMR spectra anlyses. Compound No. 48 in Table I.
EXAMPLE 31
1-sec-heptyl-3-n-heptyl-2-S-ethyl isothiourea (Intermediate)
The equipment was the same as in Example 26 above. 11.5 g (0.1 mole) 2-aminoheptane was mixed with 50 ml ethanol 2B and 15.7 g (0.1 mole) N-heptyl isothiocyanate was added, resulting in an exothermic reaction during which the temperature rose from 25.degree. to 65.degree. C. The reaction mixture was refluxed on a steam bath for 1.5 hours. 17.16 g (0.11 mole) ethyl iodide was then added to the thiourea and the mixture refluxed for 1.5 hours on a steam bath. The product was vacuum evaporated to produce 44.0 g of an isothiuronium salt. The isothiuronium salt was dissolved in 200 ml of toluene and washed with 100 cc of 5 percent sodium hydroxide. The toluene layer was then washed twice with 150 cc portions of water, dried over magnesium sulfate, filtered and vacuum evaporated. The product was then stripped under high vacuum to produce 7.78 g (92.6 weight percent of theory yield) of a clear, yellow liquid having a n.sub.D.sup.30 of 1.4768. The product was identified as the title product by IR and NMR spectra analyses.
EXAMPLE 32
1-sec-heptyl-3-n-hexyl-2-S-ethyl isothiourea (Intermediate)
The equipment, procedure and reactants were the same as in Example 31 with the exception that 10.01 g (0.07 mole) of n-hexylisothiocyanate, 8.05 g (0.07 mole) 2-aminoheptane, 35 ml ethanol 2B, 11.7 g (0.075 mole) ethyl iodide, 200 ml of toluene and a one percent solution sodium hydroxide (0.08 mole) were used as reactants and reagents in the procedure. The reaction produced 19.6 g (98 weight percent of theory yield of a clear liquid having a n.sub.D.sup.30 of 1.4765. The product was identified as the title product by IR and NMR spectra analyses.
EXAMPLE 33
1,3-di-n-heptyl-1-N-tert-butylcarbamyl-2-S-ethyl isothiourea
The equipment was the same as used in Example 26. 3.0 g (0.01 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 30 ml of methylene chloride. Two drops of triethylamine and 1 drop of dibutyltindilaurate were added to the mixture followed by 1.0 g (0.01 mole) tert-butyl isocyanate. The temperature rose from 24.degree. to 39.degree. C. The reaction mixture was stirred overnight at ambient temperature and then heated for one-half hour at 35.degree. to 40.degree. C. to complete the reaction. The reaction mixture was vacuum evaporated to produce 3.83 g (96 weight percent of theory yield) of a clear liquid having a n.sub.D.sup.30 of 1.4750. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 40 in Table I.
EXAMPLE 34
1,3-di-n-heptyl-1-N-ethylacetatecarbamyl-2-S-ethyl isothiourea
The procedure, equipment and reactants were the same as in Example 33 with the exception that 1.29 g (0.01 mole) ethylisothiocyanato acetate was used in place of the tert-butyl isocyanate. The reaction produced 4.3 g (100 weight percent of theory) of a clear liquid having a n.sub.D.sup.30 of 1.4800. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 41 in Table I.
EXAMPLE 35
1,3-di-n-heptyl-3-B-hydroxyethylcarbamyl methylcarbamyl-2-S-ethyl isothiourea
The equipment was the same as in Example 26. 9.0 g (0.03 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 30 ml of methylene chloride to which 3.87 g (0.03 mole) ethylcyano acetate was added. The temperature rose from 23.degree. to 45.degree. C. during the reaction. The mixture was allowed to stand overnight. Then 10 drops of additional isothiourea were added to react residual isocyanate. To the reaction mixture was then added 1.83 g (0.03 mole) of 2-aminoethanol and the reaction mixture was stirred overnight. The reaction mixture was vacuum evaporated to remove the methylene chloride and 25 ml of ethanol were added to the remainder of the reaction mixture. The reaction mixture was then allowed to stand for 3 days. The resultant cloudy mixture was then stirred at ambient temperature overnight, then vacuum evaporated to produce 13.7 g of a yellow, turbid liquid having a n.sub.D.sup.30 of 1.4800. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 64 in Table I.
EXAMPLE 36
Reaction product of 2 moles of 1,3-di-n-sec-heptyl-2-S-ethyl isothiourea+pp'-diphenylmethane diisocyanate
The equipment was the same as in Example 26. 3.0 g (0.01 mole) of 1,3-di-sec-heptyl-2-S-ethyl isothiourea was mixed with 30 ml of toluene. 1.25 g (0.005 mole) of pp'-diphenylmethane diisocyanate was added to the mixture, and the reaction mixture was heated and held for 2 hours at 75.degree. to 80.degree. C. The IR showed a small isocyanate peak; so 10 drops of the isothiourea was added and heating continued for 30 minutes. The reaction mixture was then stirred at ambient temperature overnight. The reaction mixture was then vacuum evaporated to produce 4.5 g (104 weight percent of theory) of an amber colored liquid having a n.sub.D.sup.30 of 1.5310. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 127 in Table I.
EXAMPLE 37
Reaction product of 2 moles of 1-N-sec-heptyl-3-N-n-hexyl-2-S-methyl-thiomethyl isothiourea+toluene 2,4-diisocyanate
The procedure and equipment were the same as in Example 36, but the reagents were 3.8 g (0.01 mole) 1-sec-heptyl-3-N-n-hexyl-2-S-methyl-thiomethyl isothiourea, 0.87 g (0.005 mole) toluene-2,4-diisocyanate and 25 ml of tetrahydrofuran. After completion of the reaction 20 drops of the isothiourea was added to react with remaining isocyanate at ambient temperature overnight. The reaction mixture was then vacuum evaporated, producing a result of 4.6 g of a red colored viscous liquid having a n.sub.D.sup.30 of 1.5344. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 138 in Table I.
EXAMPLE 38
1-N-sec-heptyl-3-N-n-octyl-n-octadecylcarbamyl-2-S-allyl isothiourea
The procedure and equipment were the same as in Example 26. 1.9 g (0.006 mole) 1-sec-heptyl-3-n-octyl-2-S-allyl isothiourea was mixed with 25 ml of tetrahydrofuran to which 1.77 g (0.006 mole) n-octadecylisocyanate was added to the mixture. The reaction mixture was then stirred at ambient temperature overnight and then vacuum evaporated to produce 3.79 g (100 weight percent of theory yield) of a clear liquid having a n.sub.D.sup.30 of 1.4769. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 144 in Table I.
EXAMPLE 39
Reaction product of 2 moles of 1-phenyl-3-n-heptyl-2-S-ethyl isothiourea+toluene-2,4-diisocyanate
The equipment was the same as used in Example 26. 2.78 g (0.01 mole) 1-phenyl-3-n-heptyl-2-S-ethyl isothiourea in 35 ml of tetrahydrofuran were mixed with 0.87 g (0.005 mole) toluene-2,4-diisocyanate. The reaction mixture was then refluxed on a steam bath for 1 hour, then 15 drops of the isothiourea was added, and the reaction mixture was refluxed for an additional hour to react all the isocyanate. The reaction mixture was vacuum evaporated to produce 4.1 g of a viscous, yellow liquid having a n.sub.D.sup.30 of 1.5737. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 151 in Table I.
EXAMPLE 40
N-(5-sila-5,5-dimethyl-1-heptyl)-N'-n-heptyl,n-octadecylcarbamyl-2-S-ethyl isothiourea
The equipment was the same as in Example 26. 2.4 g (0.007 mole) 1-(5'-sila-5',5'-dimethyl-N-heptyl)-3-n-heptyl-2-S-ethyl isothiourea in 25 ml tetrahydrofuran was mixed with 2.06 g (0.007 mole) N-octadecylisocyanate and stirred at ambient temperature for 2 hours. The reaction mixture was vacuum evaporated to produce 4.51 g (100 weight percent of theory yield) of a clear liquid having a n.sub.D.sup.30 of 1.4765. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 184 in Table I.
EXAMPLE 41
N-dichloroacetyl,N,N'-di-n-heptyl,S-ethyl isothiourea
3.0 g (0.01 mole) 1,3-di-n-heptyl-2-S-ethyl isothiourea dissolved in 25 ml of methylene chloride was placed in a three-neck 200 ml flask equipped with a magnetic stirrer. 1.1 g triethylamine was added to the mixture. Then 1.5 g (0.01 mole) dichloroacetyl chloride in 10 ml of methylene chloride was added slowly while cooling the reaction mixture in an ice bath. The reaction mixture was heated to and then held at 40.degree. C. for one-half hour. The reaction product was washed with water and the organic layer was dried with magnesium sulfate, filtered and vacuum stripped to yield 4.1 g of a liquid having a n.sub.D.sup.30 of 1.4723. The product was identified as the title product by NMR spectra analysis. Compound No. 332 in Table I.
EXAMPLE 42
Adduct of 1 mole 1,3-di-n-heptyl-2-S-ethyl isothiourea and 1 mole of diglycolic anhydride
The equipment was the same as in Example 41. 3.0 g (0.01 mole) of 1,3-di-n-heptyl-2-S-ethyl isothiourea dissolved in 15 ml glycol and 1.2 g (0.01 mole) diglycolic anhydride dissolved in 10 ml glycol were added thereto. The reaction was heated to reflux for 10 minutes and evaporated under vacuum to produce 4.1 g of a liquid having a n.sub.D.sup.30 of 1.4608. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 321 in Table I.
EXAMPLE 43
Adduct of 1 mole 1,3-di-n-heptyl-2-S-ethyl isothiourea and 1 mole of succinic anhydride
The equipment, procedures and reactants were the same as in Example 42 with the exception that 1.0 g (0.01 mole) succinic anhydride was substituted for the diglycolic anhydride. The reaction yield was 4.1 g of a semi-solid. The product was identified as the title product by NMR spectra analysis. Compound No. 331 in Table I.
EXAMPLE 44
Adduct of 1 mole 1,3-di-n-heptyl-2-S-ethyl isothiourea and 1 mole of formaldehyde
The procedure, equipment and reactants were the same as in Example 42 with the exception that 1.2 g formaldehyde as a 37 percent solution in water (0.01 mole plus approximately 20 percent excess) was substituted for the diglycolic anhydride. The reaction yield was 3.3 g of a semi-solid which was identified as the title product by NMR spectra analysis. Compound No. 323 in Table I.
EXAMPLE 45
Adduct of 1 mole 1,3-di-n-heptyl-2-S-ethyl isothiourea and 1 mole of p-anisaldehyde
The equipment, procedure and reactants were the same as in Example 42 with the exception that 1.4 g (0.01 mole) anisaldehyde was substituted for the diglycolic anhydride. The reaction yield was 4.3 g of a liquid having a n.sub.D.sup.30 of 1.4825. The product was identified as the title product by NMR spectra analysis. Compound No. 328 in Table I.
TABLE I__________________________________________________________________________ ##STR31##Compound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________1 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR32## 1.4760 2 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR33## 1.4956 3 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR34## 1.5021n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weightis 508 and n equals 9-13 and averages 11.4 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR35## 1.5440 5 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR36## Thick oiln average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7.6 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR37## 1.5283 7 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR38## 1.5254 8 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR39## 1.5235 9 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR40## 1.5215 10 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR41## 1.5186 11 C.sub. 7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR42## 1.5188 12 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR43## 1.5186 13 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.4 H.sub.9 ##STR44## 1.5180 14 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.5 H.sub.11 ##STR45## 1.5145 15 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.6 H.sub.13 ##STR46## 1.5115 16 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR47## 1.5250 17 C.sub.7 H.sub.15 C.sub.7 H.sub.15 iC.sub.4 H.sub.9 ##STR48## 1.5147 18 C.sub. 9 H.sub.19 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR49## 1.5093 19 C.sub.6 H.sub.13 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR50## 1.5214 20 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR51## 1.5175 21 C.sub.7 H.sub.15 C.sub.9 H.sub.19 C.sub.2 H.sub.5 ##STR52## 1.5170 22 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR53## 1.5134 23 C.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR54## 1.5185 24 C.sub.6 H.sub.13 C.sub.10 H.sub.21 C.sub.2 H.sub.5 ##STR55## 1.5191 25 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.4 H.sub.9 ##STR56## 1.5135 26 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.5 H.sub.11 ##STR57## 1.5125 27 C.sub.6 H.sub.13 C.sub.9 H.sub.19 C.sub.2 H.sub.5 ##STR58## 1.5179 28 C.sub.6 H.sub.13 C.sub.9 H.sub.19 C.sub.5 H.sub.11 ##STR59## 1.5120 29 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR60## 1.4750 30 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR61## 1.4786 31 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR62## 1.4800 32 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR63## 1.5180 33 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR64## 1.4970n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weightis 508 and n equals 9-13 and averages 11.34 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR65## 1.5084 35 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR66## 1.5245 36 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR67## 1.4966 37 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR68## 1.5392 38 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR69## 1.5274 39 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR70## 1.5317 40 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR71## 1.4750 41 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR72## 1.4800 42 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR73## 1.5215 43 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR74## 1.5200 44 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR75## 1.5261 45 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR76## 1.5175 46 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR77## 1.4770 47 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR78## 1.5340 48 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR79## 1.4930 49 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR80## 1.5230 50 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR81## 1.5190 51 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR82## 1.5235 52 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR83## 1.4830 53 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR84## 1.4871 54 C.sub.7 H.sub.15 C.sub.7 H.sub. 15 C.sub.2 H.sub.5 ##STR85## 1.5270 55 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR86## 1.4765 56 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR87## 1.4768 57 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR88## 1.5175 58 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR89## 1.5182 59 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR90## 1.5190 60 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR91## 1.5310 61 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR92## 1.4765 62 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR93## 1.5237 63 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR94## 1.5242 64 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR95## 1.4800 65 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR96## 1.4725 66 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR97## 1.5210 67 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub. 5 ##STR98## Soft solid 68 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR99## 1.5230 69 secC.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR100## 1.5125 70 secC.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR101## 1.5115 71 secC.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR102## 1.5205 72 secC.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR103## 1.4720 73 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR104## 1.5390 74 C.sub. 7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR105## 1.4765 75 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR106## 1.4737 76 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR107## 1.4750 77 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR108## 1.4755 78 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR109## 1.5280 79 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR110## 1.4750 80 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR111## 1.5335 81 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR112## 1.5305 82 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR113## 1.5240 83 secC.sub.7 H secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR114## 1.4740 84 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR115## 1.5295 85 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR116## 1.5201 86 sec-C.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR117## 1.4740 87 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR118## 1.5342 88 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR119## 1.5276 89 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR120## 1.4772 90 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR121## 1.5324 91 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR122## 1.5170 92 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR123## 1.5292 93 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR124## 1.5258 94 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR125## 1.4760 95 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR126## 1.5306 96 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR127## 1.5238 97 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR128## 1.5145 98 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR129## 1.5120 99 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR130## 1.5330 100 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR131## 1.5020 101 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR132## 1.5000 102 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR133## 1.5226 103 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR134## 1.5275 104 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR135## 1.5190 105 tC.sub.8 H.sub.17 2-ethyl hexyl C.sub.2 H.sub.5 ##STR136## 1.5182 106 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR137## 1.5277 107 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR138## 1.4775 108 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 SCH.sub.3 ##STR139## 1.5255 109 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR140## 1.5200 110 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR141## 1.5337 111 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR142## 1.4772 112 2-ethyl- hexyl C.sub.7 H.sub. 15 C.sub.3 H.sub.7 ##STR143## 1.5237 113 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR144## 1.4744 114 2-ethyl- hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR145## 1.5170 115 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR146## 1.5350 116 C.sub.6 H.sub.13 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR147## 1.5220__________________________________________________________________________
__________________________________________________________________________Com-pound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________117 C.sub.6 H.sub.13 2-ethyl hexyl C.sub.2 H.sub.5 ##STR148## 1.5234 118 C.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR149## 1.5190 119 2-ethyl- hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR150## 1.4765 120 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR151## 1.5120 121 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR152## 1.5124 122 2-ethyl- hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR153## 1.5264 123 2-ethyl- hexyl C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR154## 1.5296 124 2-ethyl- hexyl C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR155## 1.4770 125 C.sub.7 H.sub.15 2-ethyl hexyl C.sub.2 H.sub.5 ##STR156## 1.5393 126 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR157## 1.4763 127 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR158## 1.5310 128 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR159## 1.5340 129 C.sub.8 H.sub.17 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR160## 1.5300 130 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR161## 1.5271 131 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR162## 1.4785 132 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR163## 1.5150 133 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR164## 1.5345 134 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR165## 1.5283 135 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR166## 1.5164 136 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR167## 1.5165 137 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR168## 1.4745 138 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 CH.sub.2 SCH.sub.3 ##STR169## 1.5344 139 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR170## 1.4750 140 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR171## 1.5293 141 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR172## 1.5295 142 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR173## 1.5317 143 ##STR174## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR175## 1.5758 144 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 CHCH.sub.2 ##STR176## 1.4769 145 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 CHCH.sub.2 ##STR177## 1.5225 146 ##STR178## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR179## 1.5140 147 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR180## 1.5290 1.57357148 C.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 CHCH.sub.2 ##STR181##149 ##STR182## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR183## 1.5785 150 secC.sub.7 H.sub.15 C.sub.8 H.sub. 17 CH.sub.2 CHCH.sub.2 ##STR184## 1.5326 151 ##STR185## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR186## 1.5737 152 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR187## 1.5134 153 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR188## 1.4746 154 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR189## 1.5200 155 ##STR190## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR191## 1.5061 156 ##STR192## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR193## 1.5769 157 (C.sub.6 H.sub.5).sub.2 CH C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR194## 1.5165 158 ##STR195## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR196## 1.5860 159 C.sub.8 H.sub.17 (CH.sub.2).sub.6 Cl C.sub.2 H.sub.5 ##STR197## 1.4876 160 ##STR198## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR199## 1.5743 161 (C.sub.6 H.sub.5).sub.2 CH C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR200## 1.5760 162 secC.sub.7 H.sub.15 C.sub.12 H.sub.25 C.sub.2 H.sub.5 ##STR201## 1.4736 163 C.sub.8 H.sub.17 (CH.sub.2).sub.2 SC.sub.5 H.sub.11 C.sub.2 H.sub.5 ##STR202## 1.4850 164 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.4 H.sub.9 ##STR203## 1.4754 165 C.sub.7 H.sub.15 CH.sub.2C.sub.H CH.sub.2 C.sub.2 H.sub.5 ##STR204## 1.4810 166 C.sub.7 H.sub.15 (CH.sub.2).sub.3 OCH.sub.3 C.sub.2 H.sub.5 ##STR205## 1.4773 167 2-ethyl- hexyl O(CH.sub.2).sub.3 C.sub.3 H.sub.7 C.sub.2 H.sub.5 ##STR206## 1.4746 168 C.sub.8 H.sub.17 ##STR207## C.sub.2 H.sub.5 ##STR208## 1.5244 169 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.3 H.sub.7 ##STR209## 1.4738 170 2-ethyl- hexyl ##STR210## C.sub.2 H.sub.5 ##STR211## 1.4836 171 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.7 H.sub.15 ##STR212## 1.4735 172 secC.sub.7 H.sub.15 C.sub.9 H.sub.19 C.sub.2 H.sub.5 ##STR213## 1.4740 173 ##STR214## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR215## 1.4845 174 secC.sub.7 H.sub.15 ##STR216## C.sub.2 H.sub.5 ##STR217## 1.4930 175 2-ethyl- hexyl (CH.sub.2).sub.3 Cl C.sub.2 H.sub.5 ##STR218## 1.4950 176 C.sub.7 H.sub.15 (CH.sub.2).sub.3 OCH.sub.3 C.sub.5 H.sub.11 ##STR219## 1.4755 177 ##STR220## C.sub.7 H.sub.15 C.sub.5 H.sub.11 ##STR221## 1.4750 178 ##STR222## C.sub.7 H.sub.15 C.sub. 2 H.sub.5 ##STR223## 1.4760 179 secC.sub.7 H.sub.15 C.sub.12 H.sub.25 C.sub.2 H.sub.5 ##STR224## 1.5215 180 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.4 H.sub.9 ##STR225## 1.5295 181 C.sub.8 H.sub.17 ##STR226## C.sub.2 H.sub.5 ##STR227## 1.5205 182 secC.sub.7 H.sub.15 C.sub.12 H.sub.25 C.sub.2 H.sub.5 ##STR228## 1.5070 183 ##STR229## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR230## 1.5825 184 ##STR231## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR232## 1.4765 185 ##STR233## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR234## 1.5770 186 C.sub.8 H.sub.17 ##STR235## C.sub.2 H.sub.5 ##STR236## 1.4890 187 2-ethyl- hexyl 2-ethyl- hexyl CH.sub.2 CHCH.sub.2 ##STR237## 1.4800 188 C.sub.7 H.sub.15 (CH.sub.2).sub.3 N(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 ##STR238## 1.4780 189 2-ethyl- hexyl 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR239## 1.4757 190 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 ##STR240## ##STR241## 1.4924 191 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.4 H.sub.9 ##STR242## 1.5210 192 C.sub.8 H.sub.17 (CH.sub.2).sub.2 SC.sub.5 H.sub.11 C.sub.2 H.sub.5 ##STR243## 1.5386 193 C.sub.7 H.sub.15 CH.sub.2 CHCH.sub. 2 C.sub.2 H.sub.5 ##STR244## 1.5450 194 2-ethylhexyl- O(CH.sub.2).sub.3 C.sub.3 H.sub.7 C.sub.2 H.sub.5 ##STR245## 1.5250 195 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.3 H.sub.7 ##STR246## 1.5195 196 2-ethyl- hexyl ##STR247## C.sub.2 H.sub.5 ##STR248## 1.5395 197 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.7 H.sub.15 ##STR249## 1.5146 198 secC.sub.7 H.sub.15 ##STR250## C.sub.2 H.sub.5 ##STR251## 1.4820 199 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR252## 1.440 200 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR253## 1.4543 201 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR254## 1.4807 202 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR255## 1.4836 203 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR256## 1.4805 204 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR257## 1.4902 205 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR258## 1.5152 206 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR259## 1.517 207 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR260## 1.5207 208 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR261## 1.5215 209 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR262## 1.5273 210 ##STR263## C.sub.1 H.sub.3 ##STR264## CH.sub.3 1.5308 211 ##STR265## C.sub.1 H.sub.3 ##STR266## CH.sub.3 1.5559 212 ##STR267## C.sub.1 H.sub.3 ##STR268## CH.sub.3 Dark oil 213 ##STR269## C.sub.1 H.sub.3 ##STR270## CH.sub.3 1.548 214 ##STR271## C.sub.1 H.sub.3 ##STR272## CH.sub.3 Dark oil 215 ##STR273## C.sub.1 H.sub.3 ##STR274## CH.sub.3 1.5417__________________________________________________________________________
__________________________________________________________________________Compound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________216 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR275## 1.5785 217 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR276## 1.5838 218 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR277## 1.5800 219 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR278## 1.5710 220 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR279## 1.5700 221 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR280## 1.5680 222 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR281## 1.5720 223 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR282## 1.5746 224 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR283## 1.5726n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation inwhich the average Molecular Weight is 508 and n equals 9-13 and averages225 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR284## 1.4930 226 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR285## 1.4895 227 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR286## 1.4885 228 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR287## 1.4892 229 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR288## 1.4528 230 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR289## 1.5460 231 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR290## 1.4552 232 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR291## 1.5035 233 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR292## 1.4913 234 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR293## 1.4950 235 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR294## 1.4863 236 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR295## 1.5010 237 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR296## 1.5020 238 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR297## 1.5018 239 tC.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR298## 1.5082 240 tC.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR299## 1.5063 241 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR300## 1.5215 242 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR301## Crude solid 243 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR302## 1.5033 244 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR303## 1.5044 245 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR304## 1.4985 246 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR305## 1.4923 247 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR306## 1.4990 248 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR307## 1.4942 249 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR308## 1.5140 250 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR309## 1.5135 251 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR310## 1.4673 252 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR311## 1.5060 253 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR312## 1.5052 254 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR313## Crude solid 255 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR314## 1.4953 256 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 iC.sub.4 H.sub.9 ##STR315## 1.4953 257 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 iC.sub.4 H.sub.9 ##STR316## 1.5078 258 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 iC.sub.3 H.sub.7 ##STR317## 1.5048 259 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 iC.sub.3 H.sub.7 ##STR318## 1.5120 260 C.sub.7 H.sub.15 C.sub.1 H.sub.3 C.sub.2 H.sub.5 ##STR319## 1.5240 261 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR320## 1.5060 262 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR321## 1.5100 263 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR322## 1.5030n average = 6.2One of the reactants was Carbowax .RTM. 350 a product of Union CarbideCorporationin which the average Molecular Weight is 350 and n averages 6.2264 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR323## 1.4960 265 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR324## 1.4942 266 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR325## 1.4955n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation inwhich the average Molecular Weight is 508 and n equals 9-13 and averages267 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR326## 1.5025 268 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR327## 1.5005 269 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR328## 1.5065n average = 6.2One of the reactants was Carbowax .RTM. 350 a product of Union CarbideCorporationin which the average Molecular Weight is 350 and n averages__________________________________________________________________________6.2.
__________________________________________________________________________Com-pound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________270 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR329## Soft wax 271 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR330## 1.5166 272 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR331## 1.5200 273 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR332## 1.5024 274 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR333## 1.5240275 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR334## 1.5205 276 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR335## 1.5215 277 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR336## 1.5256 278 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR337## 1.5219 279 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR338## 1.5351 280 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR339## 1.585 281 C.sub.8 H.sub. 17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR340## 1.4974 -282 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR341## 1.5205 283 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR342## 1.5246 284 C.sub.8 H.sub.17 C.sub.6 H.sub.13 iC.sub.3 H.sub.7 ##STR343## 1.5072 285 C.sub.8 H.sub.17 C.sub.6 H.sub.13 iC.sub.3 H.sub.7 ##STR344## 1.5242 286 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR345## 1.5228 287 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub. 5 ##STR346## 1.5244 288 C.sub.8 H.sub.17 C.sub.6 H.sub.13 iC.sub.3 H.sub.7 ##STR347## 1.5286 289 C.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR348## 1.5217 290 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR349## 1.5331 291 C.sub.8 H.sub.17 C.sub.6 H.sub.13 iC.sub.3 H.sub.7 ##STR350## 1.5201 292 C.sub.8 H.sub.17 C.sub.5 H.sub.11 C.sub.2 H.sub.5 ##STR351## 1.5258 293 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR352## 1.5193 294 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR353## 1.5177 295 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR354## 1.5266 296 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 ##STR355## 1.5182 297 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SCCl.sub.3 1.5084298 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SCCl.sub.2 CFCl.sub.2 1.5091299 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SCCl.sub.2 CHCl.sub.2 1.5192 300 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR356## 1.5463 301 2-ethyl- 2-ethyl- C.sub.2 H.sub.5 SCCl.sub. 3 1.5060 hexyl hexyl 302 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR357## 1.5580 303 C.sub.4 H.sub.9 C.sub.4 H.sub.9 C.sub.8 H.sub.17 ##STR358## 1.5245 304 C.sub.8 H.sub.17 3,7-dimethyl- 2,6-octadienyl C.sub.2 H.sub.5 ##STR359## 1.4882 305 C.sub.4 H.sub.9 3,7-dimethyl- 2,6-octadienyl C.sub.2 H.sub.5 ##STR360## 1.4848 306 C.sub.1 H.sub.3 C.sub.1 H.sub.3 C.sub.14 H.sub.29 ##STR361## 1.5141 307 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.12 H.sub.25 ##STR362## 1.5091 308 2-ethyl- hexyl 2-ethyl- hexyl ##STR363## ##STR364## 1.5029 309 2-ethyl- hexyl 2-ethyl- hexyl ##STR365## ##STR366## 1.5253 310 2-ethyl- hexyl 2-ethyl- hexyl ##STR367## ##STR368## 1.4600 311 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR369## 312 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR370## 313 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR371## Low melting material314 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR372## Low- melting material 315 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR373## Low- melting material 316 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR374## Semi-solid 317 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR375## Semi-solid 318 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR376## Hygro- scopic 319 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub. 2 H.sub.5 ##STR377## 1.5425 320 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR378## Semi-solid 321 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR379## 1.4608 322 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR380## 1.4630 323 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 CH.sub.2 OH Semi-solid 324 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR381## 1.4513 325 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR382## 1.4563 326 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR383## 1.4588 327 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR384## 1.4638 328 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR385## 1.4825 329 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR386## Semi-solid 330 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR387## No line 331 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR388## Semi-solid 332 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR389## 1.4729 333 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR390## No line 334 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR391## 1.4920 335 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR392## 1.4672 336 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR393## 1.4856 337 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR394## 1.4673 338 C.sub.7 H.sub. 15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR395## 1.4560 339 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR396## 1.4870 340 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR397## 1.4830 341 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SO.sub.2 NH.sub.2 1.4660 342 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR398## 1.4632 343 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR399## 1.4670 344 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR400## 1.4874 345 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR401## 1.4670 346 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SO.sub.3 CH.sub.3 1.4325347 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SO.sub.2 NHC.sub.4 H.sub.9 1.5264 348 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR402## Glass 349 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SO.sub.2 N(C.sub.2 H.sub.5).sub.2 1.4356 350 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR403## 1.5140 351 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR404## Semi-solid 352 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR405## 1.5472 353 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR406## 1.5464 354 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR407## Stench 355 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub. 5 ##STR408## 1.4600 356 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR409## 1.4467 357 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR410## 1.5730 358 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR411## Semi-solid 359 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SCCl.sub.3 1.4880 360 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub. 5 ##STR412## 1.4640 361 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR413## 1.4670 362 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR414## 1.4780 363 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR415## 1.4990 364 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR416## 1.4970 365 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR417## 1.4915 366 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR418## 1.4922 367 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR419## Semi-solid 368 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR420## Semi-solid 369 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR421## 1.4620 370 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR422## 371 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR423## Semi-solid 372 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 SO.sub.3.sup..crclbar..HN.sup..sym. (CH.sub.3) .sub.3 Semi-solid 373 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR424## 1.4630 374 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR425## Semi-solid 375 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR426## 1.4664 376 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR427## 1.4666 377 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR428## 1.4633 378 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR429## 1.4680 379 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR430## 1.4683 380 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR431## 1.5487 381 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR432## 1.5638 382 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR433## 1.5567 383 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR434## 1.4612 384 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR435## 1.4653 385 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR436## 1.4673 386 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR437## 1.5440__________________________________________________________________________
__________________________________________________________________________Com-pound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________387 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR438## Thick oiln average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 388 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR439## 1.5021n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weight is 508 andn equals 9-13 and averages 11. 389 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR440## 1.5000 390 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR441## 391 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR442##n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weight is 508 andn equals 9-13 and averages 11. 392 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR443##n average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 393 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR444## 394 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR445##n average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 395 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR446##n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weight is 508 andn equals 9-13 and averages 11. 396 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR447## 397 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR448##n average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 398 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR449##n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weight is 508 andn equals 9-13 and averages 11.399 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR450##n average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 400 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 NH(CH.sub.2).sub.6 NCO 401 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR451## 402 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR452## 403 C.sub. 7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR453## 404 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR454##n average = 7.7One of the reactants was Carbowax .RTM. 400 a product of Union CarbideCorporation in which the average Molecular Weightis 400 and n averages 7.7. 405 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR455##n average = 11One of the reactants was Tergitol .RTM. 15-S-7 a product of Union CarbideCorporation in which the average Molecular Weight is 508 andn equals 9-13 and averages 11. 406 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR456## 407 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR457## 408 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR458## 409 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR459## 410 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR460## Liquid 411 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR461## Wax 412 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR462## Wax 413 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR463## Vis- cous liquid 414 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR464## Wax 415 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR465## Wax 416 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR466## Vis- cous liquid 417 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR467## Paste 418 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR468## Vis- cous liquid 419 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR469## Paste 420 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR470## Vis- cous liquid 421 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR471## Vis- cous liquid 422 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR472## Vis- cous liquid 423 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR473## Vis- cous liquid 424 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR474## Vis- cous liquid 425 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR475## Vis- cous liquid 426 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR476## Vis- cous liquid 427 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR477## Vis- cous liquid 428 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR478## Vis- cous liquid 429 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR479## Vis- cous liquid 430 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR480## 1.5260 431 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR481## 1.5312 432 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR482## 1.5339 433 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR483## Wax 434 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR484## Vis- cous liquid 435 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR485## 1.5628 436 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR486## 1.52526 437 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR487## 1.531 438 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR488## 1.5210 439 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR489## 1.5282 440 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR490## 1.540 441 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR491## 1.5524 442 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR492## 1.5277 443 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR493## Soft wax 444 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR494## Vis- cous liquid 445 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR495## Vis- cous liquid 446 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR496## 1.5355 447 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR497## Vis- cous liquid 448 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR498## Vis- cous liquid 449 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR499## 1.5251 450 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR500## 1.5461 451 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR501## 1.5269 452 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR502## 1.5488 453 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR503## 1.5481 454 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR504## 1.5481 455 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR505## 1.5472 456 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR506## Vis- cous liquid 457 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR507## Vis- cous liquid 458 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR508## Vis- cous liquid 459 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR509## Vis- cous liquid 460 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR510## Vis- cous liquid 461 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR511## 1.5304 462 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR512## 1.5416 463 C.sub.7 H.sub. 15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR513## Vis- cous liquid 464 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR514## Vis- cous liquid 465 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR515## Wax 466 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR516## 1.5396 467 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR517## Wax 468 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR518## 1.5325 469 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR519## 1.5304 470 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR520## 1.5311 471 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR521## 1.5378 472 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR522## 1.5250 473 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR523## Vis- cous liquid 474 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR524## 1.5484 475 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR525## 1.5124 476 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR526## 1.5172 477 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR527## 1.5548 478 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR528## 1.5206__________________________________________________________________________
__________________________________________________________________________Compound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________479 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR529## 1.5288 480 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR530## 1.5233 481 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR531## 1.5220 482 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR532## 1.5278 483 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR533## Wax 484 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR534## Viscous liquid 485 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR535## Viscous liquid 486 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR536## Viscous liquid 487 C.sub. 7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR537## Viscous liquid 488 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR538## Viscous liquid 489 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR539## 1.550 490 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR540## 1.5329 491 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR541## 1.5234 492 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR542## 1.532 493 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR543## 1.5280 494 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR544## 1.537 495 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR545## 1.5236 496 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR546## Pasty solid 497 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR547## 1.5280 498 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR548## 1.5254 499 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR549## 1.5258 500 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR550## 1.5401 501 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR551## 1.5250 502 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR552## 1.553 503 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR553## Viscous liquid 504 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR554## 1.567 505 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR555## Viscous liquid 506 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR556## 1.552 507 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR557## Viscous liquid 508 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR558## 1.542 509 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR559## Viscous liquid 510 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR560## 1.5494 511 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR561## Viscous liquid 512 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR562## 1.542 513 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR563## 1.5311 514 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR564## Soft glass 515 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR565## 1.5398 516 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR566## 1.5180 517 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR567## 1.5246 518 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR568## Soft glass 519 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR569## Very viscous liquid 520 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR570## Viscous liquid 521 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR571## Amber gel 522 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR572## Viscous liquid 523 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR573## Soft glass__________________________________________________________________________
__________________________________________________________________________CompoundNo. R R.sub.1 R.sub.2 R.sub.3 n.sub.D.sup.30 or .degree.C.__________________________________________________________________________524 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR574## 1.5429 525 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR575## 1.5460 526 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR576## 1.5430 527 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR577## Tacky solid 528 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR578## 1.5228 529 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR579## Wax 530 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR580## Wax 531 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR581## 1.5231 532 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR582## 1.5265 533 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR583## 1.5257 534 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR584## 1.5235 535 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR585## 1.5215 536 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR586## 1.5216 537 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR587## 1.5294 538 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR588## 1.5290 539 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR589## 1.5309 540 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR590## 1.5475 541 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR591## 1.5215 542 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR592## 1.5209 543 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR593## 1.5234 544 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR594## 1.5275 545 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR595## 1.5298 546 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR596## 1.5280 547 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR597## 1.5260 548 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR598## 1.5455 549 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR599## 1.5455 550 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR600## 1.5451 551 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR601## 1.5445 552 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR602## 1.5195 553 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR603## 1.5204 554 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR604## 1.5268 555 C.sub.8 H.sub.17 2-ethylhexyl C.sub.2 H.sub.5 ##STR605## 1.5466 556 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR606## 1.5007 557 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR607## 1.5180 558 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR608## 1.5185 559 2-ethylhexyl 2-ethylhexyl C.sub.3 H.sub.7 ##STR609## Waxy white solid 560 2-ethylhexyl 2-ethylhexyl C.sub.3 H.sub.7 ##STR610## 1.5420 561 2-ethylhexyl 2-ethylhexyl C.sub.3 H.sub.7 ##STR611## 1.5210 562 2-ethylhexyl 2-ethylhexyl C.sub.3 H.sub.7 ##STR612## 1.522 563 2-ethylhexyl 2-ethylhexyl C.sub.3 H.sub.7 ##STR613## 1.5236 564 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR614## 1.5231 565 C.sub.8 H.sub.17 2-ethylhexyl C.sub. 2 H.sub.5 ##STR615## 1.5279 566 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR616## 1.5278 567 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR617## 1.5278 568 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR618## 1.5270 569 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR619## 1.5240 570 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR620## 1.5410 571 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR621## 1.5209 572 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR622## Opaque white wax 573 C.sub.8 H.sub.17 2-ethylhexyl C.sub.2 H.sub.5 ##STR623## 1.524 574 C.sub.8 H.sub.17 2-ethylhexyl C.sub.2 H.sub.5 ##STR624## 1.5239 575 C.sub.8 H.sub.17 2-ethylhexyl C.sub.2 H.sub.5 ##STR625## 1.5262 576 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR626## 1.5270 577 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR627## 1.5304 578 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR628## 1.5330 579 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR629## 1.5305 580 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR630## 1.5268 581 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR631## 1.5321 582 2-ethylhexyl secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR632## 1.5415 583 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR633## 1.5406 584 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR634## 1.5233 585 2-ethylhexyl 2-ethylhexyl C.sub.2 H.sub.5 ##STR635## 1.4991__________________________________________________________________________
__________________________________________________________________________Compound n.sub.D.sup.+ orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________586 ##STR636## ##STR637## C.sub.2 H.sub.5 ##STR638## 1.5163 587 ##STR639## ##STR640## C.sub.2 H.sub.5 ##STR641## 1.5162 588 ##STR642## ##STR643## C.sub.2 H.sub.5 ##STR644## 1.4948 589 ##STR645## ##STR646## C.sub.2 H.sub.5 ##STR647## 1.5292 590 ##STR648## ##STR649## C.sub.2 H.sub.5 ##STR650## 1.5212 591 ##STR651## ##STR652## C.sub.2 H.sub.5 ##STR653## 1.5153 592 ##STR654## ##STR655## C.sub.2 H.sub.5 ##STR656## 1.5181 593 ##STR657## ##STR658## C.sub.2 H.sub.5 ##STR659## 1.5228 594 ##STR660## ##STR661## C.sub.2 H.sub.5 ##STR662## 1.5178 595 ##STR663## ##STR664## C.sub.2 H.sub.5 ##STR665## 1.5447 596 ##STR666## ##STR667## C.sub.2 H.sub.5 ##STR668## 1.5195 597 ##STR669## ##STR670## C.sub.2 H.sub.5 ##STR671## 1.5166 598 ##STR672## ##STR673## C.sub.2 H.sub.5 ##STR674## 1.5178 599 ##STR675## ##STR676## C.sub.2 H.sub.5 ##STR677## 1.5187 600 ##STR678## ##STR679## C.sub.2 H.sub.5 ##STR680## 1.5176 601 ##STR681## ##STR682## C.sub.2 H.sub.5 ##STR683## 1.5166 602 secC.sub.7 H.sub.15 tC.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR684## 1.5184 603 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR685## 1.5196 604 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR686## 1.5178 605 ##STR687## ##STR688## C.sub.3 H.sub.7 ##STR689## 1.5142 606 ##STR690## ##STR691## C.sub.3 H.sub.7 ##STR692## 1.4930 607 ##STR693## ##STR694## C.sub.3 H.sub.7 ##STR695## 1.5133 608 ##STR696## ##STR697## C.sub.3 H.sub.7 ##STR698## 1.5244 609 secC.sub.7 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR699## 1.5182 610 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR700## 1.5166 611 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR701## 1.5177 612 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR702## 1.5202 613 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR703## 1.5156 614 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR704## 1.5507 615 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR705## 1.514 616 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR706## 1.509 617 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR707## 1.5164 618 secC.sub.7 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR708## 1.5128 619 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR709## 1.5145 620 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR710## 1.5211 621 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR711## 1.514 622 ##STR712## ##STR713## C.sub.3 H.sub.7 ##STR714## 1.5118 623 ##STR715## ##STR716## C.sub.3 H.sub.7 ##STR717## 1.5157 624 ##STR718## ##STR719## C.sub.3 H.sub. 7 ##STR720## 1.5169 625 ##STR721## ##STR722## C.sub.3 H.sub.7 ##STR723## 1.5154 626 ##STR724## ##STR725## C.sub.3 H.sub.7 ##STR726## 1.5137 627 ##STR727## ##STR728## C.sub.3 H.sub.7 ##STR729## 1.5163 628 ##STR730## ##STR731## C.sub.3 H.sub.7 ##STR732## 1.5170 629 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR733## 1.5239 630 ##STR734## ##STR735## C.sub.3 H.sub.7 ##STR736## 1.5154 631 ##STR737## ##STR738## C.sub.3 H.sub.7 ##STR739## 1.5423__________________________________________________________________________
__________________________________________________________________________Com-pound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________632 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR740## 1.4488 633 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR741## 1.4564 634 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR742## 1.5583 635 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR743## 62-77.degree. 636 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR744## 1.4425 637 C.sub.7 H.sub.15 C.sub. 7 H.sub.15 SC.sub.2 H.sub.5 ##STR745## 1.4954 638 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SC.sub.2 H.sub.5 ##STR746## 1.5592n average = 6.2 One of the reactants was Carbowax .RTM. 350 a product ofUnion Carbide Corporationin which the average Molecular Weight is 250 and n averages 6.2.639 C.sub.7 H.sub.15 C.sub.7 H.sub.15 ##STR747## ##STR748## 1.4841 640 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SCH.sub.2 CH.sub.2 OH ##STR749## Waxy semi- solid 641 C.sub.7 H.sub.15 C.sub.7 H.sub.15 SCH.sub.2 CH.sub.2 OH ##STR750## Waxy solid 642 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR751## 1.4621 643 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR752## 1.4613 644 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR753## 1.4568 645 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR754## 1.4538 646 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR755## 1.4708 647 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub. 2 H.sub.5 ##STR756## 1.4412 648 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR757## 1.4553 649 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR758## 1.4501 650 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR759## 1.4654 651 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR760## 1.4990 652 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR761## 1.4764 653 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR762## 1.4563 654 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR763## 1.4689 655 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR764## 1.4836 656 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR765## 1.4660 657 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR766## 1.4623 658 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR767## 1.5095 659 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR768## Glass 660 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR769## 1.5209 661 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR770## 1.5156 662 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR771## 1.4929 663 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR772## 1.4897 664 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR773## 1.5228 665 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR774## 1.4899 666 2-ethyl- hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR775## 1.4879 667 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR776## 1.4746 668 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR777## 1.4930 669 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR778## Waxy semi- solid 670 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR779## 1.4793671 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR780## 1.4757 672 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR781## Slush 673 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR782## 1.4778 674 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR783## Slush 675 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR784## 1.4740 676 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR785## 1.4746 677 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR786## 1.4725 678 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR787## Slush 679 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR788## 1.4960 680 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR789## 1.4533 681 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR790## 1.4727 682 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR791## 1.4732 683 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR792## 1.4748 684 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR793## 1.4724 685 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR794## 1.4730 686 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR795## 1.4730 687 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR796## Slush 688 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR797## 1.4932 689 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR798## 1.4872 690 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR799## 1.4776 691 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR800## 1.4809 692 C.sub.8 H.sub.17 C.sub.5 H.sub.11 C.sub.2 H.sub.5 ##STR801## 1.4765 693 C.sub.6 H.sub.13 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR802## 1.4771 694 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR803## 1.4757 695 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR804## 1.4766 696 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR805## 1.4760 697 tC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR806## 1.4817 698 tC.sub.8 H.sub.17 C.sub.4 H.sub.9 C.sub.2 H.sub.5 ##STR807## 1.4835 699 tC.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR808## 1.4821 700 secC.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR809## 1.4752 701 tC.sub.4 H.sub.9 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR810## 1.4789 702 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR811## 1.4770 703 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR812## 1.4745 704 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR813## 1.4809 705 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR814## 1.4748 706 2-ethyl- hexyl 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR815## 1.4782 707 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR816## 1.4822 708 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR817## 1.5166 709 2-ethyl- hexyl C.sub.7 H.sub.15 C.sub. 2 H.sub.5 ##STR818## 1.4784 710 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR819## 1.4837 711 tC.sub.8 H.sub.17 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR820## 712 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.4 H.sub.9 ##STR821## 1.4748 713 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.4 H.sub.9 ##STR822## 1.5152 714 tC.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR823## 1.4808 715 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 SCH.sub.3 ##STR824## 1.4960 716 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 ##STR825## 1.4883 717 2-ethyl- hexyl C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR826## 1.4788 718 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 1.5305 ##STR827##719 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 1.5307 ##STR828##720 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR829## 1.4776 721 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR830## 1.4785 722 2-ethyl- hexyl C.sub.6 H.sub.13 CH.sub.2 SCH.sub.3 ##STR831## 1.4983 723 ##STR832## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR833## 1.5295 724 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR834## 1.4766 725 C.sub. 7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR835## 1.4738 726 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 CH.sub.2 CHCH.sub.2 ##STR836## 1.4814 727 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR837## 1.5008 728 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR838## Slurry 729 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR839## 1.4752 730 ##STR840## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR841## 1.5255 731 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub. 7 ##STR842## 1.4757 732 ##STR843## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR844## 1.4803 734 secC.sub.7 H.sub.15 C.sub.12 H.sub.25 C.sub.2 H.sub.5 ##STR845## 1.4739 735 C.sub.5 H.sub.11 S(CH.sub.2).sub.2 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR846## 1.4898 736 C.sub.7 H.sub.15 (CH.sub.2).sub.3 OCH.sub.3 C.sub.5 H.sub.11 ##STR847## 1.4772 737 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.4 H.sub.9 ##STR848## 1.4794 738 C.sub.7 H.sub.15 CH.sub.2 CH CH.sub.2 C.sub.2 H.sub.5 ##STR849## 1.4857 739 CH.sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR850## 1.4777 740 2-ethyl- hexyl-O(CH.sub.2).sub.3 C.sub.3 H.sub.7 C.sub.2 H.sub.5 ##STR851## 1.4723 741 C.sub.8 H.sub.17 ##STR852## C.sub.2 H.sub.5 ##STR853## 1.4792 742 secC.sub.7 H.sub.15 2-ethyl- hexyl iC.sub.3 H.sub.7 ##STR854## 1.4764 743 secC.sub.7 H.sub.15 2-ethyl- hexyl C.sub.7 H.sub.15 ##STR855## 1.4721 744 CH.sub.3 O(CH.sub. 2).sub.2 O(CH.sub.2).sub.3 C.sub.7 H.sub.15 C.sub.5 H.sub.11 ##STR856## 1.4757 745 ##STR857## 2-ethyl- hexyl C.sub.2 H.sub.5 ##STR858## 1.4915 746 ##STR859## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR860## 1.4943 747 secC.sub.7 H.sub.15 C.sub.9 H.sub.19 C.sub.2 H.sub.5 ##STR861## 1.4750 748 secC.sub.7 H.sub.15 ##STR862## C.sub.2 H.sub.5 ##STR863## 1.5105 749 ##STR864## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR865## 1.4740 750 C.sub.8 H.sub.17 ##STR866## C.sub.2 H.sub.5 ##STR867## 1.4936 751 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR868## 1.4948 752 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR869## 1.4922 753 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR870## 1.4916 754 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR871## 1.4894 755 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR872## 1.4898 756 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub. 2 H.sub.5 ##STR873## 1.4892 757 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR874## 1.4879 758 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR875## 1.4860 759 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR876## 1.5287 760 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR877## 1.5250 761 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR878## 1.5366 762 2-ethyl- hexyl 2-ethyl- hexyl CH.sub.2 CHCH.sub.2 ##STR879## 1.4800 763 2-ethyl- hexyl 2-ethyl- hexyl C.sub.3 H.sub.7 ##STR880## 1.4749 764 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 ##STR881## ##STR882## 1.5052 765 ##STR883## secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR884## 1.5298 766 C.sub.7 H.sub.15 (CH.sub.2).sub.3 N(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 ##STR885## 1.4786 767 secC.sub.7 H.sub.15 ##STR886## C.sub.2 H.sub.5 ##STR887## 1.4909 768 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 ##STR888## ##STR889## 1.5114 769 ##STR890## ##STR891## C.sub.2 H.sub.5 ##STR892## 1.5632 770 ##STR893## ##STR894## C.sub.2 H.sub.5 ##STR895## 1.5526 771 ##STR896## C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR897## 1.4882 772 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR898## 1.4784 773 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR899## 1.4730 774 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR900## 1.4756 775 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR901## 1.4766 776 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR902## 1.5215 777 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR903## 1.5145 778 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR904## 1.5219__________________________________________________________________________
__________________________________________________________________________Compound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________779 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR905## 1.5125 780 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR906## 1.5152 781 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR907## 1.511 782 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR908## 1.510 783 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR909## 1.5165 784 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR910## 1.5147 785 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR911## 1.5124 786 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR912## 1.5160 787 3,5,5-trimethyl hexyl 3,5,5-trimethyl hexyl C.sub.3 H.sub.7 ##STR913## 1.5250 788 2-ethyl hexyl 2-ethyl hexyl Allyl ##STR914## 1.5253 789 secC.sub.7 H.sub.15 2-ethyl hexyl iC.sub.3 H.sub.7 ##STR915## 1.5114 790 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 SCCl.sub.3 1.5001 791 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR916## Waxy solid 792 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR917## 39-45.degree. C. 793 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR918## 1.4837 794 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR919## 1.4784 795 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR920## 1.4765 796 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR921## 1.4720 797 ##STR922## ##STR923## Allyl ##STR924## 1.5777 798 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR925## 1.5608 799 secC.sub.7 H.sub.15 C.sub.8 H.sub. 17 C.sub.1 H.sub.3 ##STR926## 1.4919 800 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR927## 1.4960 801 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR928## 1.4855 802 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR929## 1.4907 803 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR930## 1.5218 804 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR931## 1.4985 805 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR932## 1.4652 806 2-ethyl hexyl 2-ethyl hexyl C.sub.2 H.sub.5 ##STR933## 1.4882 807 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR934## 1.4817 808 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR935## 1.4784 809 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR936## 1.4768 810 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR937## 1.4745 811 ##STR938## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR939## 1.4740 812 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR940## 1.4750 813 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR941## 1.4005 814 [(CH.sub.3).sub.2 CHCH.sub.2 ].sub.2 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR942## 1.4740 815 3-methyl hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR943## 1.4760 816 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR944## 1.4750 817 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR945## 1.4873 818 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR946## 1.4780 819 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR947## 1.4730 820 ##STR948## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR949## 1.4745 821 [(CH.sub.3).sub.2 CHCH.sub.2 ].sub.2 CH C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR950## 1.4740 822 3-methyl hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR951## 1.4736 823 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 ##STR952## 1.4735 824 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR953## 1.5612 825 C.sub.8 H.sub. 17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 SCCl.sub.3 1.5048 826 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 ##STR954## 1.5367 827 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 ##STR955## 1.5375 828 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR956## 1.5194 829 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR957## 1.5310 830 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR958## 1.4982 831 secC.sub.7 H.sub. 15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR959## 1.4742 832 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR960## 1.4796 833 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR961## 1.4747 834 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR962## 1.3265 835 2-ethyl hexyl 2-ethyl hexyl Allyl ##STR963## 1.4800 836 2-ethyl hexyl 2-ethyl hexyl C.sub.3 H.sub.7 ##STR964## 1.4755 837 ##STR965## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR966## 1.4750 838 C.sub.8 H.sub. 17 C.sub.6 H.sub.13 Allyl ##STR967## 1.5239 839 C.sub.8 H.sub.17 C.sub.6 H.sub.13 Allyl ##STR968## 1.4806 840 C.sub.8 H.sub.17 C.sub.6 H.sub.13 Allyl ##STR969## 1.5257 841 C.sub.8 H.sub.17 C.sub.6 H.sub.13 C.sub.3 H.sub.7 ##STR970## 1.5318 842 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR971## 1.4822 843 C.sub.8 H.sub.17 C.sub.6 H.sub.13 Allyl ##STR972## 1.4796 844 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR973## 1.4775 845 ##STR974## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR975## 1.4818 846 C.sub.8 H.sub.17 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR976## 1.5245 847 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR977## 1.4764 848 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR978## 1.4772 849 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR979## 1.4791 850 secC.sub.7 H.sub.15 C.sub.8 H.sub. 17 C.sub.2 H.sub.5 ##STR980## 1.4769 851 2-ethyl hexyl C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR981## 1.5325 852 ##STR982## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR983## 1.4785 853 (CH.sub.3 CH.sub.2 CH.sub.2).sub.2 CH C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR984## 1.4755 854 C.sub.7 H.sub.15 C.sub.7 H.sub.15 ##STR985## ##STR986## 1.5021 855 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR987## 1.5145 856 secC.sub.7 H.sub.15 C.sub. 8 H.sub.17 C.sub.2 H.sub.5 ##STR988## 1.5215 857 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR989## 1.5171 858 (n-C.sub.3 H.sub.7).sub.2 CH C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR990## 1.4775 859 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR991## 1.5400 860 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR992## 1.4945 861 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR993## 1.5076 862 (CH.sub.3 CH.sub.2 CH.sub.2 ).sub.2 CH C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR994## 1.4895 863 (CH.sub.3 CH.sub.2 CH.sub.2).sub.2 CH C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR995## 1.4755 864 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR996## 1.5119 865 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR997## 1.4848 866 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR998## 1.4851 867 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR999## 1.4974868 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1000## 1.5219 869 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1001## 1.4766 870 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1002## 1.4756 871 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1003## 1.4765 872 3-methyl hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1004## 1.4747 873 ##STR1005## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1006## 1.5230 874 ##STR1007## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1008## 1.5165 875 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1009## 1.4782 876 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1010## 1.5194 877 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1011## 1.4775 878 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1012## 1.4765 879 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1013## 1.4776 880 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1014## 1.4766 881 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1015## 1.4745 882 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1016## 1.4733 883 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1017## 1.4732 884 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1018## 1.4725 885 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1019## 1.4883 886 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1020## 1.4892 887 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1021## 1.5030 888 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1022## 1.5136 889 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1023## 1.5200 890 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1024## 1.5195 891 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1025## 1.5053 892 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1026## 1.5217 893 ##STR1027## C.sub.1 H.sub.3 C.sub.2 H.sub.5 ##STR1028## 1.5550 894 ##STR1029## C.sub.1 H.sub.3 C.sub.2 H.sub.5 ##STR1030## 29-32.degree. C. 895 ##STR1031## C.sub.1 H.sub.3 C.sub.2 H.sub.5 ##STR1032## 1.4856 896 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1033## 1.4725 897 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1034## 1.4761 898 secC.sub.7 H.sub.15 C.sub. 8 H.sub.17 C.sub.2 H.sub.5 ##STR1035## 1.4716 899 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1036## 1.4714 900 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1037## 1.5220 901 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1038## 1.4930 902 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1039## 1.4817 903 ##STR1040## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1041## 1.5805 904 ##STR1042## C.sub. 8 H.sub.17 C.sub.2 H.sub.5 ##STR1043## 1.4864 905 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1044## 1.5255 906 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1045## 1.5069 907 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1046## 1.5232 908 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1047## 1.5332 909 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR1048## 1.4801 910 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1049## 1.4762 911 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1050## 1.4772 912 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1051## 1.5230 913 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1052## 1.5152 914 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR1053## 1.4774 915 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR1054## 1.4792 916 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1055## 1.5074 917 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR1056## 1.5471 918 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1057## 1.5191 919 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1058## 1.5400 920 ##STR1059## C.sub.2 H.sub.5 C.sub.2 H.sub.5 ##STR1060## 1.4795 921 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1061## 1.5180 922 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1062## 1.5065 923 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1063## 1.5180 924 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1064## 1.5230 925 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1065## 1.5195 926 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1066## 1.5495__________________________________________________________________________
__________________________________________________________________________Compound n.sub.D.sup.30 orNo. R R.sub.1 R.sub.2 R.sub.3 .degree.C.__________________________________________________________________________927 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1067## 1.5245 928 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1068## 1.5360 9292-ethyl hexyl2-ethyl hexyl C.sub.3 H.sub.7 ##STR1069## 1.5181 930 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1070## 1.5222 931 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1071## 1.4724 9322-ethyl hexyl2-ehtyl hexyl C.sub.2 H.sub.5 ##STR1072## 1.4765 933 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1073## 1.5180 934 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1074## 1.5247 9352-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1075## 1.4775 9362-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1076## 1.5317 9372-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1077## 1.5210 9382-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1078## 1.5332 9392-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1079## 1.5440 9402-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1080## 1.5210 9412-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1081## 1.5220 9422-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1082## 1.4890 9432-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1083## 1.5165 9442-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1084## 1.5150 9452-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1085## 1.4770 946 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1086## (Spectroscopic data IR & NMR) 947 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1087## 1.4726 9482-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1088## 1.4730 9492-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1089## 1.5300 950 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1090## 1.5282 951 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1091## 1.5312 9522-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1092## 1.5210 9532-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1093## 1.5473 9542-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1094## 1.5326 9552-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1095## 1.5234 956 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1096## 1.5180 9572-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1097## 1.5172 958 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1098## 1.5122 959 (CH.sub.3 CH.sub.2 CH.sub.2).sub.2 CH C.sub.4 H.sub.5 C.sub.2 H.sub.5 ##STR1099## 1.4756 960 ##STR1100## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1101## 1.4789 9612-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1102## 1.5135 962 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 Allyl ##STR1103## 1.5176 963 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1104## 1.5130 964 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1105## 1.5138 9652-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1106## 1.4765 966 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1107## 1.4840 967 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR1108## 1.4962 968 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1109## 1.4955 969 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1110## 1.4920 970 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.4 H.sub.9 ##STR1111## 1.4909 971 C.sub.8 H.sub.17 C.sub.5 H.sub.11 C.sub.2 H.sub.5 ##STR1112## 1.4970 9722-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1113## 1.4953 973 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1114## 1.4929 9742-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1115## 1.4983 975 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1116## 1.4890 976 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1117## 1.4726 977 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1118## 1.4735 9782-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1119## 1.5165 979 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1120## 1.5080980 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1121## 1.5414 981 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1122## 1.5333 982 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1123## 1.4880 983 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1124## 1.5182 984 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1125## 1.4743 985 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1126## 1.4948 986 C.sub.8 H.sub.17 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1127## 1.5157 9872-ethyl hexyl2-ethyl hexyl C.sub.1 H.sub.3 ##STR1128## 1.5211 9882-ethyl hexyl2-ethyl hexyl C.sub.2 H.sub.5 ##STR1129## 1.4762 989 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1130## 1.5145 990 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1131## 1.5110 991 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1132## 1.5118 992 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1133## 1.5287 993 secC.sub.7 H.sub.152-ethyl hexyl C.sub.3 H.sub.7 ##STR1134## 1.5199 994 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1135## 1.5177 995 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1136## 1.5205 996 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1137## 1.5145 997 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1138## 1.5194 998 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1139## 1.5281 999 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1140## 1.4729 1000 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1141## 1.4756 1001 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1142## 1.5241 1002 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1143## 1.5164 1003 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1144## 1.5229 1004 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1145## 1.5241 1005 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1146## 1.4772 1006 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1147## 1.5142 1007 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1148## 1.4816 1008 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1149## 1.5249 1009 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1150## 1.5196 1010 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1151## 1.5300 1011 secC.sub.7 H.sub.15 C.sub.6 H.sub.13 C.sub.2 H.sub.5 ##STR1152## 1.5182 1012 C.sub.7 H.sub.15 C.sub.7 H.sub.15 Allyl ##STR1153## 1.5365 1013 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1154## 1.5150 1014 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1155## 1.4776 1015 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1156## 1.5154 1016 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1157## 1.4936 1017 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1158## 1.5255 1018 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1159## 1.5132 1019 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1160## 1.5140 1020 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1161## 1.5280 1021 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1162## 1.4718 1022 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1163## 1.5032 1023 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1164## 1.5390 1024 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1165## 1.5291 1025 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1166## 1.5188 1026 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1167## 1.5303 1027 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1168## 1.5352 1028 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1169## 1.4344 1029 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.3 H.sub.7 ##STR1170## 1.5278 1030 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1171## 1.5175 1031 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1172## 1.5322 1032 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1173## 1.4846 1033 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1174## 1.5388 1034 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1175## 1.5160 1035 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1176## 1.4723 1036 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1177## 1.5319 1037 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1178## 1.4956 1038 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1179## 1.5185 1039 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1180## 1.5152 1040 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1181## 1.5162 1041 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1182## 1.5356 1042 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1183## 1.5216 1043 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1184## 1.5286 1044 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1185## 1.5187 1045 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1186## 1.5316 1046 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1187## 1.5432 1047 secC.sub. 7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1188## 1.5229 1048 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1189## 1.4804 1049 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1190## 1.4709 1050 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1191## 1.4790 1051 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1192## 1.4754 1052 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1193## 1.4775 1053 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1194## 1.4742 1054 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1195## 1.5245 1055 secC.sub.7 H.sub.15 secC.sub.6 H.sub.13 C.sub.5 H.sub.11 ##STR1196## 1.4805 1056 secC.sub.7 H.sub.15 secC.sub.6 H.sub.13 C.sub.5 H.sub.11 ##STR1197## 1.4734 1057 secC.sub.7 H.sub.15 secC.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1198## 1.4910__________________________________________________________________________
__________________________________________________________________________Compound No. R R.sub.1 R.sub.2 R.sub.3 n.sub.D.sup.30 or .degree.C.__________________________________________________________________________1058 secC.sub.7 H.sub.15 2-ethyl hexyl i-C.sub.3 H.sub.7 ##STR1199## 1.4885 1059 3-methyl hexyl C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1200## 1.4954 1060 ##STR1201## C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1202## 1.4985 1061 ##STR1203## C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1204## 1.4985 1062 (n-C.sub.3 H.sub.7).sub.2 CH C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1205## 1.4936 1063 ##STR1206## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1207## 1.4960 1064 ##STR1208## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1209## 1.4926 1065 ##STR1210## C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1211## 1.4902 1066 ##STR1212## C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1213## 1.4915 1067 ##STR1214## ##STR1215## C.sub.3 H.sub.7 ##STR1216## 1.4909 1068 secC.sub.7 H.sub.15 secC.sub.6 H.sub.13 C.sub.5 H.sub.11 ##STR1217## 1.51221069 secC.sub.7 H.sub.15 secC.sub.6 H.sub.13 C.sub.5 H.sub.11 ##STR1218## 1.4786 1070 secC.sub.7 H.sub.15 secC.sub.6 H.sub.13 C.sub.5 H.sub.11 ##STR1219## 1.5213 1071 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1220## 1.5325 1072 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1221## 1.4720 1073 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1222## 1.5153 1074 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1223## 1.5286 1075 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1224## 1.5620 1076 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1225## 1.5403 1077 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1226## 1.5318 1078 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1227## 1.4750 1079 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1228## 1.5141 1080 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1229## 1.5380 1081 secC.sub. 8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1230## 1.4712 1082 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1231## 1.5152 1083 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1232## 1.5167 1084 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1233## 1.5159 1085 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1234## 1.4739 1086 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1235## 1.5220 1087 secC.sub.8 H.sub.17 secC.sub.7 H.sub. 15 C.sub.1 H.sub.3 ##STR1236## 1.5317 1088 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1237## 1.5298 1089 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1238## 1.5167 1090 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1239## 1.5254 1091 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1240## 1.5231 1092 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1241## 1.4950 1093 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1242## 1.5301 1094 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1243## 1.4765 1095 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1244## 1.4821 1096 secC.sub.8 H.sub.17 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1245## 1.5443 1097 ##STR1246## 2-ethyl hexyl C.sub.3 H.sub.7 ##STR1247## 1.4938 1098 ##STR1248## 2-ethyl hexyl C.sub.2 H.sub.5 ##STR1249## 1.4955 1099 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1250## 1.4987 1100 ##STR1251## 2-ethyl hexyl C.sub.2 H.sub.5 ##STR1252## 1.4934 1101 2-ethyl hexyl C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1253## 1.4926 1102 2-ethyl hexyl 2-ethyl hexyl C.sub.3 H.sub.7 ##STR1254## 1.4940 1103 ##STR1255## C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1256## 1.4940 1104 ##STR1257## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1258## 1.4959 1105 ##STR1259## C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1260## 1.4752 1106 ##STR1261## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1262## 1.4750 1107 ##STR1263## C.sub.8 H.sub.17 C.sub.3 H.sub.7 ##STR1264## 1.4747 1108 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1265## 1.4751 1109 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1266## 1.5224 1110 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1267## 1.5194 1111 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1268## 1.5306 1112 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1269## 1.5292 1113 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1270## 1.5234 1114 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1271## 1.5182 1115 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1272## 1.5238 1116 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1273## 1.54411117 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1274## 1.5410 1118 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1275## 1.4786 1119 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1276## 1.5354 1120 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1277## 1.5354 1121 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1278## 1.5232 1122 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1279## 1.5380 1123 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1280## 1.5376 1124 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1281## 1.5296 1125 C.sub.6 H.sub.13 C.sub.8 H.sub.17 C.sub.1 H.sub.3 ##STR1282## 1.5249 1126 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1283## 1.4730 1127 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1284## 1.5231 1128 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1285## 1.5232 1129 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1286## 1.5218 1130 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1287## 1.5278 1131 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1288## 1.5227 1132 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1289## 1.5174 1133 secC.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.1 H.sub.3 ##STR1290## 1.5299 1134 ##STR1291## C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1292## 1.4920 1135 C.sub.7 H.sub.15 C.sub.7 H.sub.15 C.sub.2 H.sub.5 ##STR1293## 1.4803 1136 secC.sub.7 H.sub.15 C.sub.8 H.sub.17 C.sub.2 H.sub.5 ##STR1294## 1.4950__________________________________________________________________________
III. Tobacco Budworm [Heliothis virescens (F.)]
Larvae of the tobacco budworm are used in this test in a procedure identical to that used for salt-marsh caterpillar larvae, except that a Romaine lettuce (Latuca sativa) leaf section of approximately the same size as the curly dock leaf section is used in place of the latter. The primary screening level for this test is 0.1 percent by weight of the test compound in the solution.
Table II summarizes the results of the lepidoptericidal tests performed on the compounds of Table I. These test results are expressed as LD.sub.50 values, which represent the dose of test compound which was lethal to 50 percent of the insect population in the test. The entries in Table II were obtained as follows:
For a particular lepidoptera, each compound was initially tested at the primary screening level. Those compounds showing less than 50 percent kill at this level are represented in the table by the primary screening level preceded by a "greater than" sign (>). Those compounds showing approximately 50 percent kill are represented by the primary screening level alone. Those compounds showing greater than 50 percent kill were subjected to further testing at successively lower levels, until the level was found at which approximately 50 percent kill was achieved. The latter level is listed as the LD.sub.50 for this group.
Phytotoxicity Tests
Phytotoxicity tests are conducted on cotton (Gossaypium hirsutum) and hyzini squash (Calabacita abobrinha) seedlings. Plants are grown and treated in Kaiser No. 1059 6".times.9".times.3" aluminum flats. Each flat contains one row of cotton and one row of squash, with 6-8 plants per row. The plants are grown in the greenhouse and are treated when they are approximately 8 days old and 2" tall.
Technical test compounds are diluted in a 50-50 acetone-water solution and formulated compounds are diluted in water. These test solutions are then sprayed on the flats in a Ducon-Savko Model 3400 linear spray table at rates of 1/2, 1, 2, and 4 lbs a.i./80 gallons/acre. The treated plants are then placed in the greenhouse and watered in such a way that the foliage is not wet.
One week later, the treated plants are inspected and the degree of phytotoxicity is subjectively rated from 0 to 5 as follows:
0=no injury
1=slight injury
2=slight to moderate injury
3=moderate injury
4=moderate to severe injury
5=severe injury or dead
Table II also summarizes the results of the phytotoxicity tests performed on the compounds of Table I.
The primary screening level in each of the above tests was selected for purposes of convenience only, and none of the figures in the table are to be understood as representing the highest level at which a viable test for lepidoptericidal activity can be conducted.
TABLE II______________________________________Com- Lepidoptericidal Phytotoxicitypound Activity Cotton SquashNo. SMC CL TBW 1/2 1 2 1/2 1 2______________________________________1 .008 .01 >.05 0 0 2 0 0 22 .008 .003 .04 0 0 1 0 1 23 .0024 .006 .03 0 0 3 0 1 14 .016 .0016 >.08 0 0 0 0 0 05 .003 .009 .15 1 4 4 1 4 46 .001 .005 .05 0 0 2 0 0 27 .002 .0008 .02 0 1 4 0 1 48 .0009 .0009 .02 0 1 4 0 0 39 .0007 .002 .01 1 3 5 0 2 510 .005 .0007 .02 1 3 5 1 3 511 .008 .002 >.05 0 2 5 0 2 512 .001 .002 >.05 0 1 5 0 2 513 .003 .003 >.05 1 2 5 1 2 514 .003 .005 >.05 1 3 5 0 2 415 .008 .008 >.05 1 2 5 0 1 316 .008 .008 >.05 1 3 4 0 2 417 .001 .002 >.05 1 2 4 0 1 418 .05 .003 >.05 1 2 4 0 1 319 .003 .005 >.05 0 2 5 0 2 520 .008 .002 >.05 1 2 4 0 1 321 .01 .003 >.05 0 1 2 0 1 222 .005 .0008 >.05 0 0 1 0 0 123 .003 .0005 >.05 0 1 3 0 2 424 >.05 .01 >.05 0 1 3 0 1 225 .03 .005 >.05 0 2 4 0 2 326 >.05 .01 >.05 1 2 3 0 1 227 .005 .001 >.05 0 1 3 0 1 328 >.05 .003 .05 0 1 3 0 1 229 .002 .002 >.05 0 0 0 0 0 130 .005 .002 .05 0 1 2 0 0 131 .005 .003 .05 0 1 2 0 1 332 .001 .002 .01 0 1 3 0 1 333 .008 .01 >.05 0 0 1 0 0 134 .005 .002 >.05 1 1 2 1 2 335 .01 .0005 >.05 0 1 2 1 2 336 .005 .002 >.05 0 1 2 0 1 337 .002 .002 .05 0 0 1 0 0 238 .003 .005 >.05 0 1 3 1 2 439 >.05 .1 >.05 0 0 2 0 1 340 .001 .001 .01 1 3 5 1 4 541 .003 .03 >.05 0 0 1 0 1 242 .001 .002 .05 0 2 3 1 2 543 .002 .002 >.05 0 2 5 1 3 544 >.05 .03 >.05 0 1 3 0 2 445 .01 .0005 .05 1 2 5 1 3 546 .01 .002 .05 0 0 1 0 1 247 .001 .001 .03 0 1 3 0 2 448 .005 .001 .03 1 2 4 1 3 549 .0003 .0002 .05 1 2 5 1 3 550 .0003 .0003 .05 1 3 5 1 3 551 .001 .001 .05 0 2 5 0 2 552 .005 .003 0 1 2 0 0 253 .008 .005 0 0 1 0 0 154 .008 .005 0 0 0 0 0 255 .002 .002 0 1 2 0 1 256 .001 .0003 .02 1 2 3 1 3 457 .001 .0003 .02 0 2 4 1 2 558 .002 .0005 .05 0 2 3 0 3 559 .002 .0005 .05 0 1 3 0 1 360 .003 .002 >.05 0 0 0 0 0 061 .008 .005 .05 0 2 5 0 3 562 .0008 .001 .05 0 1 2 0 1 263 .001 .005 >.05 0 0 1 0 0 264 .005 .008 >.05 0 0 1 0 0 165 .0002 .0005 .02 1 2 5 1 3 566 .002 .03 .05 0 1 3 0 2 367 .001 .002 .05 0 0 0 0 0 068 .0008 .005 .05 0 1 3 0 2 569 .0003 .002 >.05 0 1 3 0 1 570 .001 .002 >.05 0 1 3 0 1 471 .001 .0005 .05 0 1 4 0 1 472 .0008 .002 .05 0 0 1 0 1 273 .002 .003 .06 0 0 1 0 0 174 .002 .002 .03 0 0 0 0 1 075 .003 .03 >.05 0 0 0 0 0 076 .003 .03 >.05 0 0 1 0 0 177 .01 .002 >.05 0 0 1 0 0 178 .002 .0005 .05 0 1 2 0 1 379 .005 .002 >.05 0 0 0 0 0 080 .002 .0005 .01 0 0 1 0 0 181 .003 .002 .05 0 0 0 0 0 182 .008 .002 >.05 0 1 3 0 1 483 .005 .003 >.05 0 0 1 0 0 184 .001 .0003 >.05 0 1 4 0 1 585 .005 .0003 .03 0 0 3 0 0 286 .002 .0008 >.05 0 0 0 0 0 087 .002 .002 >.05 0 0 3 0 1 488 .003 .0002 >.05 0 0 3 0 0 489 .001 .002 .05 0 0 0 0 0 090 .001 .0002 .04 0 0 1 0 0 191 .0003 .0002 .01 0 0 0 0 0 192 .005 .03 >.05 0 0 0 0 0 093 .001 .001 >.05 0 0 2 0 1 394 .005 .002 >.05 0 0 1 0 0 195 .002 .0008 >.05 0 0 0 0 0 196 .001 .0003 >.05 0 2 4 1 3 597 .0008 .0008 >.05 0 0 0 0 0 098 .001 .001 .05 0 1 3 0 1 399 .002 .0005 >.05 0 0 1 0 0 2100 .003 .0005 .05 0 1 3 0 1 4101 .001 .002 .05 1 2 4 1 3 5102 .0003 .002 .06 0 0 0 0 0 1103 <.05 .002 .03 1 2 4 1 2 5104 .003 .002 .05 0 0 0 0 0 0105 .005 .002 .05 0 0 0 0 0 0106 .005 .0005 .05 0 1 4 0 2 4107 .003 .0008 .05 0 0 1 0 0 2108 .002 .001 >.05 0 1 2 0 1 3109 .003 .002 .05 0 2 4 0 3 5110 .01 .0005 >.05 0 0 2 0 0 2111 .008 .05 >.05 0 0 0 0 0 0112 .001 .0003 .05 0 0 2 0 1 3113 .005 .003 .05 0 0 0 0 0 0114 .002 .0005 .05 0 0 2 0 1 3115 .003 .008 >.05 0 0 0 0 0 0116 .002 .003 <.05 0 0 0 0 0 0117 .002 .002 >.05 0 0 0 0 0 1118 .001 .0005 <.05 0 0 1 1 2 3119 .05 .002 >.05 0 0 0 0 0 1120 .002 .001 .05 0 0 0 0 0 0121 .0005 .0005 .03 0 0 1 0 0 2122 .0001 .0005 .03 0 1 3 1 3 5123 .0003 .001 .05 1 3 4 1 4 5124 .05 .002 .05 0 1 2 0 1 3125 .0008 .001 <.05 0 0 1 0 0 1126 .0005 .0005 .03 0 1 3 1 2 4127 .0008 .005 >.05 0 1 2 1 2 5128 .001 .001 <.05 0 0 0 0 0 0129 .005 .0005 .05 0 0 1 0 1 2130 .002 .002 <.05 0 0 0 0 0 3131 .008 .002 .05 0 0 0 0 0 0132 .003 .002 <.05 0 0 1 0 1 3133 .001 .005 <.05 0 0 1 0 0 2134 .003 .001 >.1 0 0 0 0 0 1135 .0008 .0005 <.05 0 0 2 0 1 3136 .0002 .003 .05 0 0 0 0 0 1137 .001 .03 >.1 0 0 0 0 0 0138 .005 .01 >.05 0 1 2 0 1 2139 .003 .002 <.05 0 0 0 0 0 1140 .002 .001 <.05 0 0 1 0 0 0141 .0005 .0005 .05 0 0 2 0 0 1142 .01 .002 .05 0 0 0 0 0 0143 >.05 .03 .05 0 0 0 0 0 0144 .001 .002 <.05 0 0 0 0 0 0145 .0003 .0005 <.05 0 0 1 0 0 2146 >.05 .005 .05 0 0 0 0 0 0147 .005 .002 <.05 0 0 2 0 0 2148 .005 .0005 <.05 0 0 1 0 0 1149 .005 .002 .05 0 0 0 0 0 0150 .0001 .0003 <.05 0 1 2 0 1 3151 >.05 .008 <.05 0 0 0 0 0 0152 .002 .0003 .05 0 1 3 0 2 3153 .002 .001 .08 0 0 0 0 0 0154 .0003 <.001 .02 0 0 1 0 0 1155 >.05 >.05 >.05 0 0 0 0 0 0156 .03 .03 >.05 0 0 0 0 0 1157 >.05 >.05 .04 0 0 0 0 0 1158 >.05 >.05 .05 0 0 0 0 0 0159 .05 .008 >.05 0 0 0 0 0 1160 >.05 .05 >.05 0 0 1 0 0 1161 >.05 .03 .05 0 0 0 0 0 0162 >.05 .1 >.05 0 0 0 0 0 0163 >.05 .01 .04 0 0 0 0 0 0164 .008 >.05 .05 0 0 1 0 0 1165 >.05 >.05 .05 0 0 1 0 0 1166 >.05 >.05 >.05 0 0 1 0 0 1167 >.05 >.05 .05 0 1 2 0 0 1168 >.05 .01 .05 0 0 0 0 0 0169 .03 .005 >.05 0 0 0 0 0 0170 >.05 >.05 >.05 0 0 0 0 0 0171 >.05 .4 >.05 0 0 0 0 0 0172 .003 <.001 >.05 0 0 0 0 0 0173 .01 .003 >.05 0 0 0 0 0 0174 >.05 .03 >.05 0 0 1 0 0 0175 >.05 >.05 >.05 0 0 1 0 1 2176 .05 >.05 >.05 0 0 1 0 0 1177 >.05 .2 >.05 0 0 1 0 0 1178 >.05 .05 >.05 0 0 1 0 0 1179 >.05 .01 >.05 0 0 1 0 0 1180 .005 >.05 >.05 0 1 3 0 1 2181 .05 .01 >.05 0 0 0 0 0 1182 .03 .008 >.05 1 2 4 1 2 4183 >.05 >.05 .05 0 0 0 0 0 0184 .01 .003 >.05 0 0 0 0 0 0185 >.05 .5 .05 0 0 0 0 0 0186 >.05 .05 >.05 0 0 0 0 0 0187 >.05 .01 >.05 0 0 0 0 0 0188 >.05 .5 >.05 0 0 1 0 0 0189 .003 .01 >.05 0 0 1 0 0 1190 >.05 .008 >.05 0 0 0 0 0 0191 .01 .15 >.05 0 2 3 0 2 4192 >.05 .01 >.05 0 1 2 0 1 3193 .4 0 0 1 0 0 2194 .2 0 0 2 0 0 2195 .001 .002 >.05 0 1 2 0 1 3196 >.05 .01 >.05 0 1 2 0 0 2197 .2 0 0 1 0 1 2198 .5 0 1 2 0 0 1199 >.05 .2 >.05 1 2 4 1 3 5200 .01 .0025 >.05 1 3 5 2 3 5201 .05 >.05 >.05 0 0 0 0 0 0202 .05 >.05 >.05 0 0 0 0 0 0203 >.05 >.05 .03 0 0 0 0 0 0204 >.05 .1 >.05 0 0 0 0 0 0205 >.05 .1 >.05 0 0 0 0 0 0206 .03 .03 >.05 0 0 0 0 0 0207 .03 .03 >.05 0 0 0 0 0 0208 .03 .008 .05 0 0 0 0 0 0209 .01 .01 >.05 0 0 0 0 0 0210 >.05 >.05 >.05 0 0 0 0 0 0211 .05 >.05 >.05 0 0 0 0 0 0212 .01 .002 .05 0 0 1 0 0 1213 >.5 >.05 >.5 0 0 0 0 0 1214 >.05 0 0 0 0 0 1215 >.05 0 0 0 0 0 0216 .008 .005 >.05 0 0 2 0 0 1217 .05 > .05 >.05 0 0 1 0 1 2218 .05 .003 >.05 0 1 2 0 1 2219 .005 .008 >.05 0 0 0 0 0 2220 .03 .004 .05 0 0 1 0 0 1221 .01 .004 .05 0 0 1 0 1 2222 >.05 .3 >.05 0 0 0 0 0 0223 .003 .008 >.05 0 0 0 0 0 0224 .03 .002 >.05 0 0 0 0 0 1225 .01 .03 >.05 0 0 1 0 0 2226 .005 .005 >.05 0 0 1 0 0 1227 .03 .0008 >.05 0 1 2 0 1 3228 .003 .002 .05 0 1 2 0 1 2229 .01 .009 >.1 0 1 3 0 2 4230 .003 .001 >.1 1 3 5 1 3 5231 .001 .0005 >.1 2 5 5 1 5 5232 .001 .0005 >.1 0 2 5 0 2 5233 .003 .0008 >.1 1 4 5 0 3 5234 .002 .002 .1 0 2 5 0 2 5235 .003 .0008 .1 1 4 5 0 3 5236 .003 .0005 >.1 1 3 5 1 3 5237 .002 .0005 >.1 1 5 5 1 5 5238 .002 .003 >.05 0 0 0 0 0 1239 .03 .03 >.05 0 0 2 0 0 2240 .03 .03 >.05 0 1 2 0 1 3241 >.05 .005 >.05 0 0 3 0 1 5242 .01 .005 >.05 0 0 2 0 1 5243 .03 .005 >.05 0 0 3 0 1 4244 .03 .01 >.05 0 1 3 0 1 4245 .008 .03 .05 0 1 3 0 1 4246 .05 .005 >.05 0 0 2 0 1 3247 .01 .002 >.05 0 0 1 0 0 2248 .01 .01 >.05 0 0 0 0 0 0249 >.05 >.05 .05 0 0 0 0 0 0250 >.05 .2 >.05 0 0 0 0 0 0251 .01 .005 >.05 0 0 2 0 1 4252 >.05 .03 .05 0 0 1 0 0 1253 >.05 .03 >.05 0 0 0 0 0 0254 >.05 .05 >.05 0 0 0 0 0 0255 >.05 >.05 .05 0 0 0 0 0 0256 >.05 .15 >.05 0 0 0 0 0 1257 >.05 .1 >.1 0 0 0 0 0 0258 >.05 >.05 >.1 0 0 0 0 0 0259 >.05 >.05 .01 0 0 0 0 0 0260 .008 .03 >.05 0 0 0 0 0 1261 >.05 .05 >.05 0 0 0 0 0 0262 .05 >.05 >.05 0 0 0 0 0 0263 .005 .005 >.05 0 1 1 0 1 2264 .005 .005 >.05 0 0 1 0 0 1265 .03 .003 >.05 0 0 2 0 1 3266 >.05 .4 >.05 0 0 1 0 1 2267 .005 .003 >.05 0 0 0 0 1 2268 .03 .002 >.05 0 0 2 0 0 2269 .03 >.05 >.05 0 0 1 0 1 2270 .003 .002 .03 0 1 3 0 1 4271 .003 .002 .05 0 2 5 1 2 5272 .002 .002 .05 1 2 4 1 3 5273 .005 .002 .05 1 2 4 1 3 5274 .002 .001 .05 0 1 2 0 1 3275 .001 .0005 .05 0 0 2 0 1 3276 .003 .0008 >.05 0 0 2 0 1 3277 .001 .002 >.05 0 1 2 0 1 2278 .003 .001 .05 0 1 4 0 1 5279 .003 .001 >.05 0 1 2 0 1 3280 .003 .0005 .05 0 1 4 0 1 5281 .001 .001 .06 1 2 4 0 2 5282 .005 .0005 .05 1 2 4 0 1 5283 .01 .002 .05 0 1 2 0 1 3284 .001 .0008 .05 1 4 5 1 4 5285 .001 .0002 >.05 0 1 3 0 3 5286 .001 .0002 .05 0 0 2 0 0 3287 .005 .0005 .02 0 0 3 0 0 4288 .002 .0005 .02 0 0 1 0 0 1289 .002 .001 >.05 0 0 0 0 0 0290 .002 .0008 .03 0 0 0 0 0 0291 .001 .002 .05 0 0 0 0 0 0292 .003 .005 .01 0 0 0 0 0 0293 .001 .0005 .01 0 0 0 0 0 0294 .001 .0002 >.05 0 0 0 0 0 1295 .002 .03 >.05 0 0 0 0 0 0296 .0005 .001 .05 0 0 0 0 0 0297 .002 .002 .05 0 0 0 0 0 1298 .003 .005 >.05 0 0 2 0 1 2299 .008 .003 >.05 0 1 3 0 2 3300 .005 .003 .05 0 0 0 0 0 0301 .003 .001 .05 0 0 0 0 0 1302 .03 .03 >.05 0 0 1 0 1 2303 >.05 .03 >.05 0 0 0 0 0 1304 >.05 .01 >.05 0 0 0 0 0 0305 >.05 >.05 .04 0 0 0 0 0 0306 >.05 >.05 .05 0 0 1 0 1 2307 >.05 >.05 >.05 0 0 1 0 2 3308 >.05 >.05 >.05 0 0 1 0 0 1309 >.05 >.05 >.05 0 0 0 0 0 1310 >.05 >.05 .05 0 0 0 0 0 0311 .05 >.05 >.05 0 0 0 0 0 0312 .04 .05 >.05 0 0 0 0 0 0313 .002 .003 .04 0 2 4 1 3 5314 .002 .005 >.05 2 3 5 3 4 5315 <.008 <.008 .05 1 3 5 2 3 5316 .04 .04 >.05 0 0 0 0 0 0317 .05 >.05 0 0 0 0 0 1318 >.05 >.05 0 0 0 0 0 0319 .002 .002 .04 1 2 3 1 2 4320 .005 .008 >.05 0 0 1 0 0 2321 .002 .002 .02 1 2 4 2 3 5322 .002 .003 .03 1 3 5 1 3 5323 .005 .01 .05 0 1 2 0 1 2324 >.05 .5 >.05 0 0 0 0 0 0325 .03 .003 >.05 0 0 1 0 0 0326 .002 .001 .03 1 2 5 2 3 5327 .003 .002 .05 1 2 5 2 3 5328 .002 .003 .04 1 2 5 2 3 5329 .002 .003 >.05 0 1 3 1 2 3330 .002 .005 >.05 0 0 0 0 0 0331 .001 .003 >.05 0 0 0 0 0 0332 .002 .005 >.05 0 0 0 0 0 0333 >.05 >.05 >.05 0 0 0 0 0 0334 .03 .008 >.05 0 0 0 0 0 0335 >.05 .1 >.05 0 0 0 2 4 5336 >.05 .1 >.05 0 0 0 0 0 0337 .03 >.05 >.05 0 0 0 0 0 0338 .005 .002 >.05 1 3 5 1 2 5339 .005 .002 >.05 1 3 4 1 2 3340 .03 .005 .03 0 1 3 1 2 3341 .01 .008 >.05 0 2 3 1 2 3342 .01 .009 .05 0 0 1 0 1 2343 .002 .005 >.05 0 2 3 1 2 4344 >.05 .1 >.05 0 0 0 0 0 0345 .002 .003 .03 0 1 3 1 2 3346 .03 .008 >.05 0 0 0 0 0 1347 .03 .009 >.05 0 0 0 0 0 0348 .005 .002 .05 0 1 4 0 1 3349 >.05 .05 >.05 0 2 4 0 2 3350 .005 .005 .03 0 1 4 1 2 3351 .03 .005 >.05 0 1 2 1 2 3352 .005 .003 >.05 0 0 2 1 1 2353 .03 .002 .05 0 0 0 0 0 0354 .002 .002 .01 0 0 0 0 0 0355 .002 .001 .05 0 3 4 1 2 5356 .005 .005 >.05 0 1 2 0 2 4357 .03 .005 .05 0 0 0 0 0 0358 .05 >.05 .05 0 0 0 0 0 0359 .002 .005 .05 0 2 3 1 2 2360 .005 .002 .05 0 1 3 1 2 3361 .01 .003 >.05 0 0 0 0 0 0362 .008 .008 >.05 0 0 0 0 0 0363 .05 .002 .05 0 0 0 0 0 0364 .005 .002 .05 0 0 1 0 0 1365 >.05 .2 >.05 0 0 0 0 0 0366 >.05 >.05 .05 0 0 0 0 0 0367 .003 .005 >.05 0 1 2 0 1 2368 >.05 .03 .05 0 0 0 0 0 0369 .003 .003 .05 0 1 2 0 1 2370 .005 .005 .05 0 0 2 0 0 2371 .003 .008 .05 0 1 3 0 1 2372 .002 .002 >.05 0 0 1 0 1 2373 .002 .005 >.05 0 2 4 1 2 3374 .001 .002 >.05 0 1 2 0 1 2375 .002 .002 >.05 0 0 0 0 0 0376 .003 .005 .05377 .002 .0005 .05 0 0 0 0 0 1378 .003 .005 .05 0 0 0 0 0 1379 .002 .003 .05 0 0 0 0 0 0380 .002 .0003 .05 0 0 0 0 0 0381 .002 .003 >.05 0 0 0 0 0 0382 .002 .0005 .1 0 0 0 0 0 0383 .001 .002 .05 0 1 2 1 2 3384 .002 .0008 .05 0 0 0 0 0 1385 .002 .0005 .05 0 0 1 0 0 2386 .016 .0016 >.08 0 0 0 0 0 0387 .003 .009 .15 1 4 4 1 4 4388 .0024 .006 .03 0 0 3 0 1 1389 .004 .0008 >.1 0 0 2 0 0 2390 .05 .03 .05391 >.05 >.05 >.05392 >.05 >.05 .05393 .01 .01 >.1 0 0 0 0 0 0394 .05 .03 >.1 0 0 0 0 0 0395 .05 >.05 >.1 0 1 3 0 1 2396 .01 .005 >.1 0 0 0 0 0 0397 .05 >.05 >.1 0 0 0 0 0 2398 .05 .003 >.1 0 1 3 0 2 3399 .01 .01 .03 0 0 0 0 0 0400 .05 .04 0 0 0 0 0 0401 .002 .002 1 2 5 1 3 5402 .05 >.05 0 0 0 0 0 0403 .001 .002 0 2 4 1 2 5404 .03 .008 0 0 0 0 0 0405 .03 .01 0 0 0 0 0 1406 .03 .03 0 0 0 0 0 0407 .03 .008 0 0 0 0 0 1408 .03 .03 >.05 0 0 0 0 0 0409 .003 .005 >.05 0 0 0 0 0 0410 .0008 .002 .05 0 0 0 0 0 1411 .005 .002 .04 0 1 3 1 3 4412 .003 .002 >.05 0 0 2 0 0 2413 .003 .001 .04 0 0 0 0 0 0414 .005 .003 .04 0 0 1 0 0 1415 .002 .001 .04 0 1 3 0 1 2416 .005 .002 .04 0 0 0 0 0 1417 .003 .0025 >.05 0 0 0 0 0 0418 .008 .003 >.05 0 0 0 0 0 0419 .002 .0025 .05 0 0 0 0 0 0420 .01 .003 >.05 0 0 0 0 0 0421 .002 .005 .03 0 0 1 0 0 2422 .005 .002 .05 0 0 1 0 0 2423 .008 .003 <.01 0 0 0 0 0 2424 .03 .001 .05 0 0 0 0 0 0425 .01 .002 >.05 0 0 2 0 0 2426 .01 .005 >.05 0 1 2 0 1 2427 .01 .002 >.05 0 0 0 0 0 0428 .03 .005 >.05 0 0 0 0 0 0429 .002 .001 >.05 0 0 0 0 0 0430 .005 .002 >.05 0 0 0 0 0 1431 .01 .002 >.05 0 0 0 0 0 2432 .005 .005 >.05 0 0 2 0 0 2433 .005 .005 >.05 0 0 0 0 0 0434 .01 .03 >.05 0 0 0 0 0 0435 .01 .002 >.05 0 0 0 0 0 0436 .003 .001 .05 0 0 0 0 0 1437 .005 .001 >.05 0 0 0 0 0 0438 .003 .002 >.05 0 0 1 0 0 1439 .003 .003 >.05 0 0 1 0 0 2440 .003 .003 >.05 0 0 0 0 0 0441 .005 .002 >.05 0 0 0 0 0 0442 .003 .005 >.05 0 0 0 0 0 2443 .003 .005 >.05 0 0 0 0 0 0444 .008 .01 >.05 0 0 0 0 0 0445 .001 .01 >.05 0 0 0 0 0 0446 .003 .008 >.05 0 0 0 0 0 0447 .008 .01 >.05 0 0 0 0 0 0448 .005 .005 >.05 0 0 0 0 0 1449 .008 .005 >.05 0 0 0 0 0 0450 .005 .005 >.05 0 0 0 0 0 0451 .005 .03 .05 0 0 0 0 0 0452 .001 .001 .05 0 0 0 0 0 0453 .002 .005 .05 0 0 0 0 0 0454 .001 .003 >.05 0 0 0 0 0 0455 .008 .002 .06 0 0 1 0 0 1456 .002 .002 .05 0 0 0 0 0 0457 .005 .002 .05 0 0 0 0 0 0458 .005 .01 >.05 0 0 0 0 0 0459 .008 .01 .05 0 0 0 0 0 0460 .003 .002 >.05 0 0 0 0 0 0461 .005 .002 >.05 0 0 0 0 0 0462 .005 .002 >.05 0 0 0 0 0 0463 .005 .005 .05 0 0 0 0 0 0464 .002 .005 .05 0 0 0 0 0 0465 .005 .002 >.05 0 0 0 0 0 0466 .003 .002 .05 0 0 0 0 0 0467 .003 .002 >.05 0 0 1 1 0 2468 .002 .002 >.05 0 0 0 0 0 0469 .002 .002 >.05 0 0 0 0 0 0470 .002 .003 .05 0 0 0 0 0 0471 .002 .005 >.05 0 0 0 0 0 0472 .003 .005 >.05 0 0 0 0 0 1473 .002 .002 >.05 0 0 0 0 0 0474 .002 .002 .05 0 0 0 0 0 1475 .002 .005 >.05 0 0 0 0 0 1476 .002 .002 .05 0 0 0 0 0 0477 .005 .002 >.05 0 0 0 0 0 0478 .003 .002 >.05 0 0 0 0 0 0479 .005 .01 .05 0 0 0 0 0 0480 .003 .002 >.05 0 0 0 0 0 0481 .003 .002 .03 0 0 0 0 0 1482 .008 .003 .05 0 0 0 0 0 1483 .005 .002 >.05 0 0 0 0 0 0484 .003 .002 >.05 0 0 0 0 0 0485 .003 .002 >.05 0 0 0 0 0 0486 .005 .002 >.05 0 0 0 0 0 0487 .001 .005 >.05 0 0 0 0 0 0488 .003 .002 .05 0 0 0 0 0 1489 .01 .002 >.05 0 0 0 0 0 0490 .002 .002 >.05 0 0 0 0 0 0491 .005 .003 >.05 0 0 0 0 0 0492 .003 .002 >.05 0 0 0 0 0 0493 .005 .005 >.05 0 0 0 0 0 1494 .01 .005 >.05 0 0 0 0 0 0495 .01 .002 >.05 0 0 0 0 0 0496 .003 .001 >.05 0 0 0 0 0 0497 .001 .002 .01 0 0 0 0 0 0498 .0008 .005 .03 0 0 0 0 0 0499 .002 .002 .01 0 0 0 0 0 0500 .003 .002 .05 0 0 0 0 0 0501 .002 .002 .03 0 0 0 0 0 0502 .003 .002 >.05 0 0 0 0 0 0503 .002 .001 >.05 0 0 0 0 0 0504 .005 .002 >.05 0 0 0 0 0 0505 .008 .001 >.05 0 0 0 0 0 0506 .002 .003 .01 0 0 0 0 0 0507 .002 .005 >.05 0 0 0 0 0 0508 .001 .002 .03 0 0 0 0 0 0509 .001 .002 .05 0 0 0 0 0 0510 .005 .001 >.05 0 0 0 0 0 0511 .001 .005 >.05 0 0 0 0 0 0512 .001 .005 .05 0 0 1 0 0 1513 .002 .005 >.05 0 0 1 0 0 1514 .005 .006 >.05 0 0 0 0 0 0515 .002 .002 .05 0 0 0 0 0 0516 .001 .005 >.05 0 0 0 0 0 0517 .002 .002 >.05 0 0 1 0 0 1518 .003 .005 >.05 0 0 0 0 0 1519 .001 .005 >.05 0 0 0 0 0 0520 .001 .005 >.05 0 0 0 0 0 0521 .008 .003 >.05 0 0 0 0 0 0522 .005 .003 >.05 0 0 0 0 0 0523 .005 .005 >.05 0 0 0 0 0 0524 .002 .0002 >.05 0 0 0 0 0 0525 .002 .001 >.05 0 0 0 0 0 0526 .002 .0005 >.05 0 0 0 0 0 0527 .002 .0003 >.05 0 0 0 0 0 0528 .002 .0002 .05 0 0 1 0 1 3529 .002 .0002 >.05 0 0 0 0 0 0530 .002 .001 >.05 0 0 0 0 0 0531 .002 .001 >.05 0 0 0 0 0 0532 .001 .0002 .05 0 0 0 0 0 2533 .002 .0001 <.05 0 0 0 0 0 0534 .002 .002 .05 0 0 0 0 0 0535 .002 .0002 >.05 0 0 0 0 0 0536 .002 .0005 >.05 0 0 0 0 0 0537 .001 .0005 .05 0 0 0 0 0 0538 .002 .002 .05 0 0 0 0 0 0539 .001 .0005 .05 0 0 0 0 0 0540 .002 .0001 .05 0 0 0 0 0 0541 .0002 .001 .05 0 0 0 0 0 0542 .03 .002 .05 0 0 0 0 0 0543 .0005 .0003 >.05 0 0 0 0 0 0544 .002 .0001 .05 0 0 0 0 0 0545 .03 .002 .05 0 0 0 0 0 0546 .001 .0001 .05 0 0 0 0 0 0547 .0005 .0005 .05 0 0 1 0 0 3548 .001 .0003 <.05 0 0 1 0 0 1549 .002 .0002 .05 0 0 0 0 0 0550 .002 .0002 .05 0 0 0 0 0 0551 .03 .001 .05 0 0 1 0 0 1552 .0003 .0002 .05 0 0 0 0 0 1553 .001 .0003 <.05 0 0 0 0 0 1554 .001 .0003 .05 0 0 0 0 0 0555 .002 .0008 >.05 0 0 0 0 0 0556 .0005 .0001 >.05 0 0 0 0 0 1557 .0005 .0002 .05 0 0 0 0 0 2558 .0002 .0003 >.05 0 0 0 0 0 0559 .003 .002 .05 0 0 1 0 0 1560 .003 .002 >.05 0 0 0 0 0 1561 .001 .002 .03 0 1 3 0 1 5562 .001 .001 .05 0 0 2 0 0 2563 .001 .0003 .05 0 0 0 0 0 0564 .003 .0005 >.05 0 0 2 0 1 3565 .002 .0005 >.05 0 1 2 0 1 2566 .0005 .0005 .05 0 0 2 0 1 3567 .0003 .0005 .05 0 0 2 0 1 2568 .0003 .0002 >.05 0 0 1 0 1 2569 .0008 .0003 .02 0 0 0 0 0 1570 .0003 .0003 .05 0 0 1 0 0 1571 .0005 .0003 >.05 0 0 2 0 1 2572 .0002 .0002 .05 0 0 2 0 1 3573 .001 .0005 > .05 0 0 1 0 1 2574 .001 .0005 >.05 0 0 2 0 1 2575 .01 .0008 >.05 0 0 1 0 1 2576 .0002 .0005 >.05 0 0 1 0 0 2577 .002 .0003 .05 0 0 1 0 0 2578 .0005 .0005 >.05 0 0 1 0 0 2579 .0005 .0005 >.05 0 0 1 0 0 2580 .0005 .0008 >.05 0 0 0 0 0 1581 .0002 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51020 .0008 .0005 >.05 0 0 1 0 0 01021 .002 .005 >.05 0 0 1 0 0 01022 .0003 .0002 .05 0 1 2 0 1 31023 .0005 .0002 >.05 0 0 1 0 0 11024 .002 .002 >.05 0 0 2 0 0 21025 .001 .0005 >.05 0 1 2 0 0 11026 .0008 .002 >.05 0 0 2 0 0 11027 .0003 .0005 >.05 0 1 2 0 0 11028 .0005 .001 >.05 1 2 4 1 3 51029 .002 .002 >.05 0 0 1 0 0 01030 .0005 .0002 .01 0 1 2 0 1 31031 .0005 .0002 .05 0 0 1 0 0 01032 .002 .0005 .03 0 0 1 0 0 21033 .002 .0002 .008 0 1 2 0 1 21034 .002 .001 .03 0 1 2 1 2 31035 .001 .0005 .01 0 1 3 1 2 41036 .001 .0008 .008 0 0 1 0 0 01037 .0005 .0005 .03 0 1 2 0 1 21038 .002 .0008 .01 0 1 2 0 1 21039 .002 .0003 .05 0 1 2 0 1 21040 .0005 .0002 .005 0 1 2 1 2 31041 .002 .002 .05 0 0 0 0 0 01042 .003 .0005 .008 1 2 3 0 1 31043 .002 .0005 .03 0 1 2 1 2 41044 .001 .0005 .008 0 1 3 1 2 41045 .002 .0005 .008 0 1 2 0 1 31046 .001 .0005 .01 0 1 3 0 1 31047 .002 .0005 .008 0 1 2 0 1 31048 .002 .002 .031049 .0005 .0005 .03 1 2 5 2 4 51050 .002 .0005 .03 0 1 3 1 2 41051 .0005 .002 .03 0 1 2 0 1 21052 .003 .0005 >.05 0 2 3 1 2 31053 .0005 .002 .05 1 2 3 0 1 31054 .0008 .0005 .03 1 2 4 1 3 41055 .03 >.05 >.05 1 3 4 1 3 51056 .002 .005 >.05 1 3 5 1 2 41057 .005 .005 >.05 0 1 3 0 2 31058 .005 .03 >.05 0 0 2 0 1 21059 >.05 >.05 .05 0 0 0 0 0 01060 .003 .03 .05 0 0 1 0 0 01061 >.05 >.05 >.05 0 0 0 0 0 01062 >.05 >.05 >.05 0 0 0 0 0 01063 >.05 .01 >.05 0 0 0 0 0 01064 .005 .005 >.05 0 0 1 0 0 01065 .008 .005 .05 0 0 0 0 0 01066 .03 .03 >.05 0 0 0 0 0 01067 >.05 >.05 >.05 0 0 0 0 0 01068 .005 .03 >.05 0 1 3 0 1 31069 .002 .01 >.05 1 3 5 1 3 51070 .005 .01 .05 0 0 1 0 0 11071 .0002 .0005 .03 0 0 2 0 0 11072 .002 .0005 >.05 0 0 1 0 0 01073 .0005 .0002 .03 1 2 3 1 2 41074 .0005 .0005 >.05 0 1 2 0 0 21075 .002 .0005 .03 1 2 3 1 2 31076 .0005 .0002 .008 0 1 2 0 1 31077 .0003 .0002 .05 0 0 0 0 0 01078 .0005 .0005 .01 1 1 3 0 2 31079 .0005 .0005 .05 1 2 3 1 2 41080 .0005 .0005 .01 0 0 1 0 0 11081 .0005 .0005 .03 0 1 3 1 2 41082 .0003 .0005 .01 1 2 4 1 3 51083 .0005 .0005 .03 0 1 3 0 1 31084 .002 .0005 .03 0 1 3 0 1 31085 .0005 .002 .05 0 1 2 0 0 11086 .0005 .0005 .03 0 0 2 0 0 21087 .0005 .0008 >.05 0 1 2 0 1 21088 .0005 .0005 .05 0 0 0 0 0 01089 .0005 .0005 .01 0 0 2 0 1 31090 .002 .0005 .03 0 1 2 0 1 31091 .001 .0005 .05 0 1 2 0 0 21092 .001 .0008 >.05 0 1 2 0 1 31093 .002 .0005 .01 0 1 2 0 0 21094 .002 .0005 .05 0 0 1 0 0 11095 .003 .002 .05 0 0 0 0 0 01096 .002 .0005 .05 0 0 1 0 0 11097 .03 .003 >.05 0 0 0 0 0 01098 .03 .002 .05 0 0 0 0 0 01099 >.05 >.05 >.05 0 0 0 0 0 01100 .005 .008 >.05 0 0 0 0 0 01101 >.05 >.05 >.05 0 0 0 0 0 01102 >.05 >.05 >.05 0 0 0 0 0 01103 .005 .005 >.05 0 0 0 0 0 01104 .005 .005 >.05 0 0 0 0 0 01105 .002 .0005 -- 0 0 0 0 0 01106 .003 .0005 >.05 0 0 0 0 0 01107 .002 .002 >.05 0 0 0 0 0 01108 .03 .01 >.051109 .03 .005 .051110 .01 .002 >.051111 .03 .005 >.051112 .008 .002 >.051113 .03 .005 .051114 .005 .002 .051115 .03 .005 <.051116 .01 .005 >.051117 .005 .002 .051118 .03 .005 >.051119 .01 .005 >.051120 .01 .008 >.051121 .01 .005 >.051122 .01 .002 .051123 .03 .005 >.051124 .003 .005 >.051125 .005 .005 >.051126 .008 .03 >.051127 .003 .003 >.051128 <.001 .005 >.051129 .002 .005 >.051130 .002 .005 <.051131 .002 .005 <.051132 .002 .003 <.051133 .001 .002 <.051134 .01 .005 >.05 0 0 0 0 0 01135 .01 .01 .051136 -- <.003 >.05______________________________________ Symbols for Table II SMC: saltmarsh caterpillar CL: cabbage looper TBW: tobacco budworm >: greater than <: less than
Biocidal Tests
In Vitro Vial Tests
Tubes of sterilized nutrient and malt extract broth were prepared. Aliquots of the toxicant, dissolved in an appropriate solvent, were injected through the stopper, into the broth, to provide concentrations ranging from 50 ppm downward. The test organisms consisted of one fungi, Botrytus cinerea, and one bacteria, Staphylococcus aureus (S.a.) Roseenbach.
Three drops of a spore suspension of each of the fungi were injected into the tubes of malt broth and three drops of the bacteria were injected into the nutrient broth. One week later the growth of each organism was observed and effectiveness of the chemical was recorded as the lowest concentration in ppm which provided 100 percent inhibition of growth as compared to untreated inoculated tubes. The results are shown in Table III.
Fungicidal Tests
Foliar Preventive Sprays
Bean Powdery Mildew--The chemicals were dissolved in an appropriate solvent and diluted with water containing several drops of a wetting agent. Test concentrations, ranging from 1000 ppm downward, were sprayed to runoff on the primary leaves of pinto beans (Phaseolus vulgaris L.). After the plants were dry, the leaves were dusted with spores of the powdery mildew fungus (Erysiphe polygoni de Candolle) and the plants were retained in the greenhouse until the fungal growth appeared on the leaf surface. Effectiveness was recorded as the lowest concentration, in ppm, which will provide 75 percent or greater reduction in mycelial growth on the leaf surface as compared to untreated, inoculated plants. The results are shown in Table III.
TABLE III______________________________________ Biocides Fungicides LC-100 (ppm) LC-75-100 (ppm) Botyrytus Bean PowderyCompound No. Staph aureus cinerea Mildew______________________________________118 (10) 5 1155 -- -- 500166 -- -- 500170 -- -- 500175 -- -- 1000183 5 (10) 500213 10 -- 500279 0.125 5 500309 25 10 500310 0 5 --554 10 0.125 500662 25 10 --733 -- -- 500741 50 50 10769 -- -- 500878 10 5 5______________________________________ () = partial control 50% or greater
The primary screening level in each of the above tests was selected for purposes of convenience only, and none of the figures in the table are to be understood as representing the highest level at which a viable test for lepidoptericidal activity can be conducted.
The compounds of this invention are generally used in formulations suitable for convenient application. In general, such formulations will contain inert or other active ingredients or diluent carriers in addition to the active compound. Examples of such ingredients or carriers are organic solvents, such as sesame oil, xylene range solvents, and heavy petroleum; water; emulsifying agents; surface active agents; talc; pyrophyllite; diatomite; gypsum; clays; and propellants, such as dichlorodifluoromethane.
The active compounds can further be combined with dust carriers for application as dusts, with granular carriers for application by fertilizer spreaders or ground or airplane seeders. It also can be formulated as a wettable powder or a flowable for application as a water suspension, or with solvents and surface active materials for application as sprays, aerosols, or emulsions. The compounds or their formulated mixtures can be applied to any habitat of the pests. Examples of such habitats are insect dwellings, clothing, plant surfaces, and soil. If desired, however, the active compositions can be applied directly to organic matter, seeds or feedstuffs in general, upon which the pests feed, or directly to the pests themselves. When applied in such a manner, it will be advantageous to use a formulation which is not volatile.
Particularly preferred compositions are those comprising an insecticidally effective amount of the active compound in combination with an inert insoluble solid carrier vehicle. Examples of such compositions are wettable powders, dusts, and flowable formulations, in which the solid carrier is in finely divided form; and granular formulations, in which the solid carrier is a pre-formed granule.
These isothiourea compounds can also be formulated to include baits that induce feeding responses in the lepidoptera larva resulting in earlier ingestion of the lepidoptericidal isothioureas. Effective baits include cottonseed flour, cottonseed oil, extract of mature cottonseed, sucrose, invert sugar, citrus molasses, soybean oil, soy flour, corn oil, extract of corn kernels, extract of corn silks, extract of corn seed and mixtures thereof together with suitable emulsifiers and wetting agents.
The amount of active compound or formulation which is considered to be insecticidally effective is that amount which, when applied to the pest habitat or feedstuff, will kill or substantially injure a significant portion residing or feeding thereon. The active compounds of this invention can be employed either as the sole pesticide component of the formulations or as one of a mixture of compounds in the formulation having similar utility. Furthermore, the presently disclosed pesticide compositions need not be active as such. The purposes of this invention will be fully served by a composition which is rendered active by external influences, such as light, or by physiological action occurring when the preparation is ingested or penetrates into the body of the pest.
The precise manner in which the pesticide compounds of this invention are used in any particular instance will be readily apparent to a person skilled in the art. Generally, the active pesticidal compound will be used as a component of a liquid composition; for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide compound in the present formulation can vary within rather wide limits, ordinarily, the pesticide composition will comprise not more than about 50.0 percent by weight of the formulation.

Number	Name	Date
4062892	Fancher et al.	Dec 1977
4233318	Fancher et al.	Nov 1980
4328247	Drabek et al.	May 1982
4357351	Fancher et al.	Nov 1982

Lepidoptericidal isothiourea compounds

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