LEP1DOPTERICIDAL ISOTHIOUREA COMPOUNDS

Background of the Invention

Lepidoptericidai isothiuronium compounds have been disclosed in the prior art particularly those described in U.S. Patents 3,969,511 and 4,062,892 and have the formula

SR« i- ^Δ N=C-NHR ₁ .

These compounds have a major disadvantage in that they show high levels of phytotoxic activity and thus, although control¬ ling lepidoptera in the crop to be protected, ≤LΓG 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 lepidoptericidai 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

SR« } ²

R_N=C-NR, i J-

R

wherein R and R-, are independently selected from the group consisting of:

^C 2~ ^C 10 ^alk yl, preferably alkyl, more preferably Cg-Cg alkyl, ^G 2" ^C 10 ^al koxyalkyl, preferably Cc-Cg alkoxyalkyl, more preferably ^c 6" ^c 8 iko y ikyi ^and phenyl and R and R., together contain from 12 to 22 carbon atoms;

wherein R« is selected from the group consisting of:

lkyl, more pre era y Cn-Cg a yl,

^C 3~ ^G 10 ^a ^enyl, preferably C -Cr alkenyl, more preferably C ₂ -C^ alkenyl,

Cn-C, alkynyl, hydroxyalkyl, preferably C2-C hydroxyalkyl

^C 2~ ^C _β ^alζ y ^lthioalk y ¹ 3 preferably C ₂ "C^ alkyl hio- alkyl,

^C 2~ ^C 6 ^a lkyloxyalkyl, preferably C ₂ ~C alkylthioalkyl, (CH ₂ ) _n [X(CH ₂ ) _n ] y where n = 1 or 2,

X is 0 or S and y = 1-4, preferably

1-2, 0 -(CH ₂ ) COH where n = 1-10, preferably 1-5, more preferably 1-3, phenyl and phene hyl;

is selected from the group consisting o ^■ p .

carboalkoxyalkyl wherein the alkyl is

^C 1~ ^C 4 ^a ^kyl, preferably C^-C ₂ alkyl, alkylketoalkyl wherein the alkyl is

^C 1~ ^C 4 ^alk l, preferably C-,-C ₂ alkyl, hydroxyalkenyl wherein the alkenyl is

the alkyl is C-, -C-, ₂ alkyl, preferably C-.-Cg alkyl, more preferably C-1-C alkyl, formylhydroxyme h l, hydroxyhaloethyl wherein the halo is chloro, bromo or iodo, preferably chloro or bromo, more preferably chloro, substituted phenoxyalkyl wherein the alkyl is C^-C ₂ alkyl, preferably C-, alkyl and the substituents are p-methoxy, Cl, N0 ₃ or CN,

wherein R is -OH, -NH ₂ or

^C 1" ^C 4 ^al koxy, preferably methoxy,

OH OH ^ ^R 2

/ < 1

■CH-CHN-C=NR ₁ wherein R, R^ and ₂ are R as defined above,

wherein R, R- _j _ and R ₂ are as defined above,

Θ jf, © _r

•PO 'B, -P0 ₂ *B or -S0 «B wherein B is a basic cation, preferably an organic basic cation, more preferably an organic basic cation selected from the group consisting of

Θ θ

(CH ₃ ) ₃ NH and ^ ^{1 5}

wherein R/ is selected from the group consisting of:

-H,

" ^C 1" ^C 22 ^a ^yl, preferably C- _j _-C-, ₂ alkyl, more preferably C^-Cg alkyl and most preferably C^-Cg alkyl, hydroxyethyl, naphthyl, phenyl, substituted phenyl wherein the substituents are independently selected from the group of halogen, preferably chlorine, C-,-C _c alkyl, - UR£

preferably C^-C ₂ alkyl, C^-Ce alkoxy, preferably C _η -C alkoxy, nitro, cyano

and R ₂ are as defined above,

0 SR

II I

-(CH ₂ )gNHCN-C=NR ₁ wherein R, R _j _ and R2 R are as defined above,

and R ₂ are as e ne a ove,

wherein R, R _χ and ₂ are as defined above,

wherein R, R- _j _ and R ₂ are as defined above,

^JRl

0 ^ ^R 2

wherein x is 1 to 8 and R, R^ and R« are as defined above,

wherein m is 2 or 3 and R, R-, and R ₂ are as defined above,

wherein R, R^_ and R ₂ are as defined above,

wherein R, R- _j _ and ₂ are as defined above ,

0

II

wherein X is selected from the group consisting of: 0, s,

NH, and

NR _n ; Y is hydrogen or methyl; and R-, _Q is selected from the group consisting of:

H,

^C 1" ^C 18 ^al kyl, preferably

C- _j -Cg alkyl, more preferably

^C 1" ^C 2 ^a3 - ^k yl _s C -C^ alkenyl,

^c 3" ^c 4 ^{alk n} y ¹ »

C ₂ -C haloalkyl, preferably C ₂ -C ₃ haloalkyl,

^c 7" ^c 2o °iy ^{c c} i ^oa ^yi>

-8-

C ₂ -Cι g-polyalkoxyalk l, C -Cg hydroxyalkyl,

^C 3" ^C 10 ^al kox ai yi ₉

Co -Cg carboalkoxy alkyl, 5 ^c 4" ^c 8 ^{c c} l° ^a lk: l3lkyl,

C# -Cg alkylcycloalkyl, preferably

Cg-Cg alkylcycloalkyl, • CA -Cy cyclo lkylimino, C ₂ -C _{η Q} alkylind.no , 10 ^c l" ^c 3 ^a lkylamino,

CA-CJ_ ₂ dialkyla inoalkyl,

^C 6" ^G 10 ^{c c} ^- ^oa ^ ^en ^> phenyl, alkylphenyl wherein the alkyl 15 is C ₁ -C ₄ , parachloroalkylphenyl wherein the alkyl is C-^-C, , naphthyl, anthracenyl, 20 benzamidocycloalkyl wherein the alkyl is C^-C ₂ , pyranylmεthyl, tetrahydrof rfuryl, thiophenemethyl, 25 benzhydryl, halobenzhydr 1, polycyclic alcohol, and substituted phenyl wherein the substituents are selected 30 from the group consisting of:

C ₁ -C ₄ alkyl, halogen, nitro, trifluoromethyl, 35 formyl,

-9- chlorαacetyl,

C^C^ alkoxy, hydrogen, benzyl, 5 chlorobenzyl, phenethyl, and substituted phenethyl wherein the substituents are selected from the group of:

10 ^G l~ ^c 4 ^a ^kyl and halogen, and is selected from the group consisting of: C ₁ -C alkyl, 15 ^G " ^G 6 ^koxyalkyl, and

Co-C ₄ alkenyl, R, _Q and R-,-, taken together form . . heterocyclic compounds, preferably heterocyclic compounds selected 20 from the group consisting of: azepinyl, morpholinyl, piperdinyl,

Ci-Co alkyl substituted 25 piperdinyl, and

Y is hydrogen or methyl provided that. hen X = 0 or S then R-, _Q is other than hydrogen and substituted 30 phenyl wherein the substituents are selected from the group consisting of: halogen, ^c l" ^c 4 ^al ^o ,

"BURE4 >

0Λ1P

-10- phenox , trifluoromethyl, C ₁ -Cg thioalk l, nitro, 5 isocyanato,

^C 2" ^C 4 P ^{ol alicoχ} y> C ₃ -C ₇ cycloalkyl, ^G 3~ ^G 2 ^car boalkoxyalkyl, preferably C ₃ ~C-J_Q 10 carboalkoxyalk l,

Ci-Cg haloalkyl, preferably

C-v-C, haloalkyl, ^C 3~ ^C 12 ^a ^enyl, preferably

C ₃ -C ₄ alkenyl, 15 • C -C dialkylamino, phenylamino, Ci-C ₂₄ lkyl, preferably

^G ι" ^c 4 ^al!< yi, ^G ₃ " ^c i ₂ k rσ ai iamido ik i, 20 ^c ₅ " ^c ιo ^N J ^N ~k ^{droχ al} k i rei oaik i, isocyanatoalk l wherein the alkyl is C-^-Cr,

^C 3" ^C 12 ^a lkylamidoalk l polyalkoxyamidoalk l wherein 25 the polyalkoxy moiety contains from 3-6 repeating C ₂ ~C ₃ alkoxy units and the amidoalkyl moiety contains from 4-12 carbon atoms, 30 -S0 ₂ C1,

-S0 ₂ polyalkoxyamidoalkyl wherein the polyalkoxy moiety contains from

^UR£

3-6 repeating C ₂ -C alkoxy units and the amidoalkyl moiety contains from 4-12 carbon atoms,

Re is selected from the group consisting of: hydroge ; ^c ι ^"c 4 ^al y ^χ »

C ₃ -Cg alkoxyalkyl,

C ₃ -C ₄ alkenyl, hydroxyethyl, and phenyl, RA and Re taken together form heterocyclic compounds, preferably heterocyclic compounds selected from the group consisting of: azepinyl, morpholinyl, piperdinyli and

C-i-C alkyl substituted piperdinyl,

0

1/ ^■ CX _n Rg wherein X is 0 or S, n is 0 or 1,

Rg is selected from the group consisting of: ^c l~ ^c 18 ^a ^-kyl, preferably

^C 1" ^C 12 ^a ^ ^ς 7^-» ^more preferably

C ₁ -C ₄ alkyl, C ₂ -C ₆ haloalkyl, phenyl, and substituted phenyl x^herein when N = 1 the substituents are selected from the group consisting of: nitro, chloro^

C- _j _-C ₂ alkyl,

C ₄ ~Cg polyalkoxyalkyl,

C ₃ -Cg cycloalkyl, C ₃ -C ₄ alkenyl, C -Cg lkoxyalkyl, C ₂ ~Cg hydroxyalkyl, 5 ^l"^3 carboxyalkyl, and

Ce-C ₈ trialkylammoniumalkyl salts, and when n = 0 the substituents are selected from the group consisting of: L0 chloro - ₃ thiopotassium,

^C 1~ ^C 18 ^a ^-kyl, preferably

^G 1" ^G 12 ^a ^-kyl, more preferab C _χ -C ₄ alkyl, L5 benzyl,

Cτ-C ₂ heteroalkyl, C ₂ -C ₄ chlorocarboxyalkyl, C ₄ -C _fi polyalkoxyalkyl ± and acetyl,

20 wherein R ₇ is selected from the group consisting of:

-(CH ₂ -)_ wherein n = 0 to 8,

-CH=CH-,

therein M is H or Cl,

15 -ύ

O PI

-13-

-CC1=CC1-,

-CH ₂ OCH ₂ -, and

-OCH ₂ CH ₂ 0-, and d = 0 or 1, and when d = 1 Y is selected from the group consisting of:

-0,

-S, and

-NH, Z is selected from the group consisting of:

^G l" ^C 18 ^al kyl, preferably alkyl, more preferably alkyl, hydrogen,

C -C ₁ g polyalkoxyalkyl,

C ₄ -Cg dialkylaminoalkyl, phenyl, substituted phenyl, organic salts, inorganic salts, and when d = 0, Z is

Cl or

SR

-N-C=NR wherein R,

/

R

R, and R ₂ are as defined above,

OMPI

0 n -P Rg) ₂ wherein Rg is selected from the group consisting of: 1~ ^G 10 ^a ^ox , preferably

^G 1" ^G 5 ^alkoχ y>

5 - a ino,

C-J-C-J _Q alkoxyamino, preferably C-t-C-_ alkoxyamino, hydroxy-, and 10 organic base

-SO^Elg wherein w = 0-2 and R^ is selected from the group consisting of:

ammo,

15 ^G 1" ^G 10 preferably

C ₁ -C ₅ alkyl,

C^-C ₄ haloalkyl, phenyl ;

^G l" 10 ^i^k lamino, 20 ^G l" ^G 10 ^a lkylaminθj

^G 1" ^G 10 ^a ^ox , preferably

^G 1" ^G 5 ^a ^ko y, substituted phenyl x?herei the substituents are selec 25 from the group consisting nitro, chloro,

^G 1" ^G 4 ^a ^yl i ^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 shoxra by the following formula:

SR 1

R-N=CNHR

The formation of the prior art isothioureas is well knoxm in the art. They are derived by the reaction of an isothiocyanate xtfith 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 belox?:

S

R-NCS H ₂ N-R' -> RNHCNHR ²

SR

R'X R-N=CNHR HX

X = 1, Br or Cl

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 neu¬ tralization of an isothiourea salt with a cold aqueous soluti of atase 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 add ing 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 tri- ethylamine, 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 solven such as benzene in which trie hylamine hydrohalide is almost totally insoluble, filtering off the triethylamine hydrohalid and treating the filtrate with the isocyanate or acid chlorid completing the reaction as discussed previously. Solvents suitable for the condensation of the isothiourea x Lth an isocyanate or acid chloride are those which are unreactive to any of the reactants. These include hexane, benzene, toluene, tetrahydrofur n, dioxane, me hylenechloride, diethylether, and the like. Depending on the reactants, reaction temperatu are generally within the range of -20°C to 80°C and reaction times vary from 0.5 hours to 24 hours.

In some instances, it has been found that the con¬ densation of an isothiourea with an isocyanate or acid chlorid can be hastened by the addition of such catalysts as triethylamine and dibutyltindilaurate.

MPI

Equations showing the reactions just discussed are as follows:

A) Using isothiourea base with an isocyanate

B) Using isothiourea salt + a base

C) Using isothiourea base with an acid chloride

JS' ^s C ₁ + Et ₃ ^• HCl

O=CR ₃

- RE ζT

-18-

The isothiourea precursors of the prior art discussed above can in general be prepared by the method disclosed in U.S. Patents 3,969,511 and 4,062,892.

These compounds are useful as lepidoptericides when used in a lepidoptericidally effective amount on in of the order lepidoptera or their habitat or feedstuffs. of the compounds also show phytotoxic effects which coul render them useful as herbicides as well as lepidopteric if such efficacy was desired. In addition, some of thes compounds show biocidal and/or fungicidal effects.

By "lepidoptericidally effective amount" is me the amount of the herein disclosed lepidoptericidai comp which when applied in any conventional manner to the hab of the lepidoptera, the feedstuffs of lepidoptera, or th insects themselves, will "control" by killing or substan injuring a significant portion of the lepidoptera.

These compounds are useful in protecting food, forage crops and ornamental crops from damage by insects larva of other order lepidoptera. Examples of crops to protected include forest trees such as oak and pine, fru trees such as peach, apple and walnut, vegetables such a tomatoes, other crops such as tobacco, cotton, lettuce, corn and rice and any crop which lepidoptera feed upon.

The novel compounds of this present invention be prepared from the above precursors by methods shown i the following examples.

l,3-Diheptyl-2-ethyl-3-(Q,Q-dimethyl phosphoro) isothiourea

6.0 grams (g) (0.02 mole ) of l,3-diheρtyl-2- ethyl isothiourea and 200 milliliters (ml) of methylene chloride were combined in a 500 ml 3-neck flask fitted ^■ with a stirrer, thermometer and dropping funnel. The 5 solution was stirred and cooled to 0°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 to 5°C. After the 0 addition was complete, the reaction mass was stirred at 0°C for 30 minutes. Then, a solution of 8.7 g (0.04 mole ) of 25 percent sodium methoxide in methanol xrith 25 ml of methylenechloride was added over a period of 15 minutes while the pot temperature was maintained at 0 to 5°C. 5 The reaction mass was then stirred at 5°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 MgS0 ₄ , filtered and evaporated invacuo to yield 7.4 g of the desired product, 1,3- diheρtyl-2-ethyl-3-(0,0-dimethylphosphoro) isothiourea

30 which had a n _D of 1.4528. The product identification was confirmed by infrared (IE.) , H-nuclear magnetic resonance (NMR) and C 13-NMR spectra. Compound No, 229 5 in Table I.

O PI

-20-

Example 2

l,3-diheρtyl-2-ethyl-3- N-f4-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-nitrσphenyl- isocyanate, 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 exother had sub¬ sided, 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-nitroρhenyl) carbowax (350 carbamate, n 30 1.4810. The structure was confirmed by C 13-NMR spec ^Ό tra.

Intermediate b)

7 g (0.013 mole) of intermediate a) was dissolv in 200 ml of ethanol in a Parr glass pressure bottle. 1 g of palladium on carbon catalyst was added and the mixtu 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-me hyl-5-amino- phenyl) carbox^ax (350) carbamate. The structure was confirmed by C 13-NMR spectra.

Interαediate 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°C and saturated with 5 HC1 gas. The mixture was then heated to reflux and phosgene was bubbled in for 30 minutes. The reaction mass became clear. N 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-isocyanoρhehyl)

30 0 carboxrax (350) carbamate , τiZ 1.5848 . The s tructure

13 was confirmed by C -NMR spectra.

l,3-diheρtyl-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 l,3-diheρtyl-2-ethylisothiourea, 2 drops of triethylamine and 15 ml of methylene chloride were 5 combined ii 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, l,3-diheρtyl-2- ethyl-3- N-[4-methyl-3-(carbowax-350-carbamyl) phenyl carbamyl isothiourea. The structure was confirmed by 0 C -NMR spectra. Compound No.216 in Table I.

Examole 3

1,3-diheptyl-2-ethyl-3-fN-(3-tergitol (15-S-7) oxycarbamylphenyl) carbamyl] isothiourea

The title compound was formed as follox-zs:

Intermediate d)

In the same manner as intermediate a) of Example 2 above, 3.28 g (0.02 mole) of 3-nitroρhenyliso- cyanate, 10.1 g of tergitol (15-S-7), 2 drops of tri¬ ethylamine and 25 ml of methylene chloride were combined to yield 13.2 g of the desired compound, N-(3-nitroρhenyl) tergitol (15-S-7) carbamate. Structure x?as 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 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 treate xtfith excess HC1 ga.s follox^ed by excess phosgene to yield 9.4 g of the desired compound, N-(3-isocyanophenyl) tergit (15-S-7) carbamate. Structure x?as confirmed by IR spectra.

l,3-diheptyl-2-ethyl-3-fN-(3-tergitol (15-S -7) oxycarba ylτihenyl) carbamyl] isothiourea

In the same manner as the title compound of Example 2 above, was prepared 2 g (0.003 mole) of intermediate f) as combined x .th 0.9 g (0.003 mole) of l,3-diheptyl-2-ethylisothiourea, 2 drops of triethylamine and 10 ml of methylene chloride to yield 2.9 g of the desired product, l,3-diheptyl-2-ethyl-3-[N-(3-tergitol (15-S-7) oxycarbamylphenyl) carbamyl] isothiourea n _D 30

1.5710. Structure was confirmed by IR spectra. Compound No. 219 in Table I.

Example 4

l,3-diheptyl-2-ethyl-3-(0,0-diethylphosphorodithioyl acetyl) isothiourea

Intermediate g) 30 g (0.1 mole) of l,3-diheρtyl-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°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^, filtered and evaporated invacuo to yield 36.1 g of the desired compound, l,3-diheptyl-2-ethyl-3-chloroacetylisothiourea. The structure was confirmed by IR and NMR spectra.

1,3-diheptyl-2-ethyl-3-(0,O-diethylphosphorodithioyl acetyl isothiourea

2.2 g (0.012 mole) of 0,0-diethyldithiophosphoric acid was dissolved in 25 ml of acetone and was treated with 5 g of anhydrous potassium carbonate. After neutraliza¬ tion, 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 x?as stirred at room temperature for 2 hours, then was poured into two 200 ml of toluene. The resulting mixture ^ s x^ashed xd.th two 200 ml portions of water. The toluene phase was then dried with anhydrous MgS0 , filtered and evaporated invacuo to yield 3.6 g of the desired product, l,3-diheptyl-2-ethyl- 3-(0,0-diethylphosphorodithioylacetyl) isothiourea. n _D 30

1.5060. The structure -was confirmed by IR and NMR spectra.

Compound No. 261 in Table I.

Exaππsle 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 ^f -diheρtyl-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 dropxd.se to the above solution at 0°C. The mixture was stirred 1.5 hours at room temperature then at 30-35°C for 1.5 hours. The cooled solution ^as washed twice with 20 ml water, once with 25 ml saturated sodium bicarbonate solution and twice more x Lth 20 ml of water. The organic phase was dried

.2 g 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~ 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 .1.

Example 7

l,3-di-n-heρtyl-l-trichloromethylthio-2-ethyl isothiourea

3 g (0.01 mole) l,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 x?as rinsed tx-?ice 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

30 resulting liquid had a nj of 1,5084 and s identified as the title compound by IR spectrum and mass spectroscopy. Compound No. 297 in Table I.

O PI

Example 8

1,3-di-n-heptyl-l- (2'-fluoro -1' ,1* ,2' ,2 ^f -tetrachloroethylthio 2-ethylisothioxιrea

2.0 g (0.007 mole) l,3-di-n-heρtyl-2-ethyl iso¬ thiourea was dissolved in 100 ml tetrahydrofuran and placed in a stirred round bottom flask and placed in an ice bath. 0.7 g (.0069 mole) triethylamine was added and the mixture stirred for 10 minutes. 1.68 g (.0068 mole) 2-fluor0-1,1,2,2- 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 washe twice with 20 ml tetrahydrofuran. The filtrate was vacuum evaporated. The title product's yield was 3.53 g of a liquid having a EL 3.0 of 1.5091. The product identity was confirmed by IR spectrum and mass spectroscopy. Compound No. 298 in

Table I.

Example 9

l,3-di-n-heptyl-l-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) l,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 iight broxm 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 5 a nr 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-l,3-diheptyl-3-(2-carboethoxy) ethyl-2-isothiourea

3 g (0.01 mole) of S-ethyl-l,3-diheptyl-2-iso- . thiourea and 3 g (0.03 mole) of ethyl acrylate x?ere placed in a 100 ml glass flask. A catalytic amount of base 0 (0,1 g NaH) was added and the mixture heated from 25 to 85°C and held at 85°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 5 was verified by IR and NMR spectra.

Compound No. 199 in Table I.

Example 11

S-ethyl-l,3-diheptyl-3-(3-oxobutyl)-2-isothiourea

The procedure was the same as for Example 10 except ethyl acrylate was replaced with methyl vinyl ke one and the reaction was run at room temperature for 4 hours. Work-up of the product was the same. 2 g 0 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-heρtyl- '-ethyloxalyl-S-ethyl-isothiourea

5.0 g (16.6 millimoles) of S-ethyl-l,3-diheρtyl- 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°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 to 15°C. A large amount of a white precipitate formed x .thin seconds and stirring was allowed to continue for 1 hour at 0°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 NaHC0 ₃ , 3 times with 10 ml portions of water, once with 10 ml of saturated sodium chloride and dried over N ₂ SO ₄ . The dried, clear yellox? organic solutio was filtered through N ₂ SO ₄ and the solvent was removed under vacuum to yield 6.63 g (99.7% yield) of the title

30 product as a clear, yellow oil having a nl 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

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Example 13

Bis-N' - (N,N ^l -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

5 chloride was substituted for the ethyloxalyl chloride of the previous example. The reaction resulted in a clear yellow solution which was stirred at 0°C for 1 hour and then stirred at room temperature for 20 hours. The clear yellow solution was then transferred to a separatory funnel 0 containing 50 ml of water and 50 ml of methylene chloride. The layers xere 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 ₂ S0 . 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 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, '-Pi-(1-heρtyl -N'-(ethylmercapto carbonyl -S-ethyl isothiourea 0 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-(l-heρ ^' tyl)-S-ethyl isothiourea and 1.85 g (18.3 millimoles) of triethylamine and 50 ml of methylene chlorde x*ere added to the flask followed by addition of 2.28 g (18.3 millimoles) of ethylthio chloroformate. The resultant product was phase separated,

1fURl4 -

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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 ΏZ 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.

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1,3-diheptyl-2-ethyl-3-f3'-2' ^f -ethoxyethoxycarbonylamino)- 4 ^! -meth lphenylaminocarbonyl) isothiourea

The- title product was prepared as follows:

^' Step a) l,3-diheptyl-2-ethyl-3-(3-isocyanato-4-methylρhenyl- aminocarbonyl) 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 xras then added to the methylene chloride. Next, 25.8 g (0.086 mole) of l,3-diheρtyl-2-ethyl isothiourea ^ s added without cooling over a period of 5 minutes. The temperature increased from 20 to approximately 30°C during this addition. The reaction mixture x*as then heated to reflux (41°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

30 of product having a τ^ of 1.5318 which was identified as the intermediate title product by IR and carbon 13 NMR spectra.

Step b) Preparation of l,3-diheptyl-2-ethyl-3-[3 ^f -(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 to 68°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

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bath temperature of 80 to 90°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-f3 ^r -(3 ^f '-chloro^' '-methylphenyl- ureido)-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 x^as 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

l,3-diheptyl-2-ethyl-3-f3'-propylureido-4'-methylphenyl¬ aminocarbonyl] 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 x?as exothermic and the temperature rose about 10 to 20°C. No heat was applied to the mixture and the reaction was completed in 1 hour. The mixture ras filtered from a small amount of solid by-product and x?as worked up in the manner of Example 15 b) . - The reaction produced

5.0 g of a liquid having a n^° of 1.5312 and was identified as the title product by IR and carbon 13 NMR spectra analyses.. Compound No. 431 in Table I.

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l,3-diheρtyl-2-ethyl-3f3 ^t -p-chloroben2ylthiocarbonylamino- 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-chloro- ^' benzylmercaptan x?as 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'-methyl ¬ phenylaminocarbonyl) isothiourea

The reactants were the same as in Example 15 b) with the exception that 0.99 g (0.0105 mole) of phenol x*as substituted for the 2-ethoxyethanol. The reaction produced 5.2 g of a liquid having a n _D 30 of 1.5488 xtfhich was identified as the title product by NMR and IR spectra analyses.. Compound No. 452 in Table I.

Example 20

l-octyl-2-ethyl-3-sec-heρtyl-3-f3-(l-octyl-2-propyl-3- sec-heρtyl-3-carbonylamino)-4-methylphenylcarbonylamino] isothiourea

Step a) Preparation of l-octyl-2-ethyl-3-sec-heρtyl-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 l-octyl-2-ethyl-3-sec-heptyl-

isothiourea was substituted for the thiourea reactant of step 25 a). The reaction produced 41.5 g (98.8 x^eight percent of theory) of a liquid having a n~ 30 of 1.5280 which identified as the title intermediate by IR and carbon 13 NMR spectra analyses,

Step b) Preparation of l-octyl-2-ethyl-3-sec-heρtyl-3- '[3-(l-octyl-2-propyl-3-sec-heptyl-3-carbonylamino)-4- methylphenylcarbonylamino] isothiourea.

The title product was prepared in the manner of step 15 b) xdLth 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 l-octyl-2-proρyl-3-sec-heptyl isothiourea.

The reaction produced 7.9 g (96.3 weight percent of theory) of a liquid having a ι 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

l,3-bis-n-heptyl-l-(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 *7ith a magnetic stirrer, thermometer and dropping funnel. A solution of 18 g of the l,3-diheptyl-2- ethyl isothiourea (in 100 ml dry methylene chloride) was added dropxd.se 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°C. The solution xvas then stirred at about 25 ^β 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^° of 1.4833

JR! ^"

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was recovered. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 635 in Table I.

Example 22

l,3-bis-n-heptyl-l-chlorocarbonyl-2-ethyl isothiourea

100 ml of dry CH ₂ C1 ₂ was placed in a 500 ml flask equipped with a thermometer and dropping funnel and cooled to 5°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 ₂ C1 ₂ , 10.1 g triethyl¬ amine and 30 g of l,3-diheptyl-2-ethyl isothiourea was added dropwise over a one hour period at 5°C. The mixture was then stirred overnight at ambient temperature.

The next morning the reaction mixture was warmed to about 40 ^β C for 2 1/2 - 3 hours to ensure completion of the reaction. The mixture was then subjected to reduced pressure to remove the CH ₂ C1 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- 3,0 of 1.4613 was recovered. The product was identified as the title product by mass spectra analyses. Compound No. 643 in Table I.

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Example 23

l,3-bi≤-n-heρtyl-l-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 to 30°C. The mixture was then heated to 45-50°C for 3 hours. The reaction mixture was then cooled to 15°C and washed twice by 50 ml portions of cold water. The benzene phase was dried by MgS0 ₄ , filtered and the solvent removed under reduced pressure. 5.75 g of a liquid (96 weight percent of theory) having a IL 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

l,3-bis-n-heρtyl-l-(proρargyloxycarbonyl)-2-ethyl isothioure

50 ml of dry tetrahydrofuran and 0.36 g of NaH wer 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 l,3-diheρtyl-2-ethyl isothiourea carbamyl chloride was added dropwise over 10 minutes. The mixture was stirred and warmed to 45°C for 2 hours. The reaction was cooled to 25°C and filtered by suction on a glass frit and filter.

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The solvent was removed under reduced pressure. 5.0 g of a liquid (88 weight percent of theory) having a n. 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-ethyIhexyl)-!-(succinic anhydride adduct)2-ethyl- isothiourea'Et N salt.

200 ml of dry CH ₂ C1 ₂ , 32.8 g of 1,3-(2-ethyIhexyl)- 2-ethyl isothiourea, 11 g of succinic anhydride and 11.I g of EtgN 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 _Q 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 l,3-di-(2'-eth lhexyl)-2- S-ethyl isothiourea -f- ^' toluene-2,4-diisocyanate

In a three-neck 200 ml flask equipped xdth a magnetic stirrer, 3.28 g (0.01 mole) of l,3-di-(2'-ethyl- hexy1-2-S-ethyl isothiourea was mixed with 20 ml of tetra¬ hydrofuran. To this solution was added 0.87 g (0.005 mole) of toluene-2,4-diisocyanate. The temperature rose from

23°C to 34 ^β 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 meth lenechloride 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- 3.0 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-l-N-phenylcarba_myl-2-S-n-propyl isothiourea Ij i

The equipment was as in Example 26 above. 6.2 g (0.014 mole l,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-xd.se addition of 1.43 g (0.014 mole) triethylamine xdth 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 chloro¬ form 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.

5 The product was 5.9 g (96.7 weight percent of theory yield) of a yellow liquid having a 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

l,3-di-n-heptyl-l-N-octadecylcarbamyl-2-S-ethyl isothiourea

. The equipment was the same as in Example 26 above. Q 4.5 g (0.015 mole) l,3-di-n-heρtyl-2-S-ethyl-isothiourea was mixed xd.th 40 ml tetrahydrofuran and 4.43 g (0,015 mole) N-octadecylisocyanate was added. Three drops of triethyl¬ amine were added and the mixture stood overnight. The mixture was then warmed to 40°C for 20 minutes to complete 5 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. 30 of 1.4750. The product was identified as the title product by IR and NMR spectra 0 analyses. Compound No. 29 in Table I.

Example 29

l,3-di-n-heptyl-l-N-4-methylthiophenylcarbamyl-2-S-Ȧ 4;thyl isothiourea

The equipment was the same as in Example 26 above. 3.0 g (0.01 mole) l,3-di-n-heρtyl-2-S -ethyl isothiourea was mixed xd.th 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° to 33°. 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 on τi 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

l,3-di-n-heptyl-l-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_ 3.0 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

l-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-aminσheptane 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 to 65°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 ^

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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- 3.0 of 1.4768. The product was identified as the title product by IR and NMR spectra analyses.

Example 32

l-sec-heρtyl-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 _Q 30 of

1,4765. The product was identified as the title product by

IR and NMR spectra analyses.

Example 33

l,3-di-n-heptyl-l-N-tert-butylcarbamyl-2-S-ethyl isothiourea

The equipment was the same as used in Example 26, 3.0 g (0.01-mole) l,3-di-n-heptyl-2-S-ethyl isothiourea was mixed with 30 ml of methylene chloride. Two drops of tri¬ ethylamine 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 to 39°C. The reaction mixture was

stirred overnight at ambient temperature and then heated fo one-half hour at 35 to 40°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 havin a 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-l-N-ethylacetatecarbamyl-2-S-ethyl isothiou

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- 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-hydroxyeth lcarbamyl methylcarbamyl-2-S- ethyl isothiourea

The equipment was the same as in Example 26.

9.0 g (0.03 mole) l,3-di-n-heρtyl-2-S-ethyl isothiourea was mixed xdth 30 ml of methylene chloride to which 3.87 g (0.03 mole) ethylcyano acetate was added. The temperature rose from 23 to 45°C during the reaction. The mixture was allowe 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 reactio mixture was vacuum evaporated to remove the methylene chlori and 25 ml of ethanol were added to the remainder of the

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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 ~ 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 l,3-di-n-sec-heptyl-2-S- ethyl isothiourea + p '-diphenylmethane diisocyanate

The equipment was the same as in Example 26. 3,0 g (0.01 mole) of l,3-di-sec-heptyl-2-S-ethyl isothiourea was mixed xd.th 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 to 80°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 _D 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 l-N-sec-heptyl-3-N-n-hexyl-2-S- ethyl-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, .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 xdth remaining isocyanate at ambient temperature overnight. The reaction mixture was then vacuum evaporated, producing a result of 5 4.6 g of a red colored viscous liquid having a n_ 3.0 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

l-N-sec-heptyl-3-N-n-octyl-n-octadecylcarbamyl-2-S-allyl isothiourea

The procedure and equipment were the same as in 0 Example 26. 1.9 g (0.006 mole) l-sec-heρtyl-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 5 produce 3.79 g (100 weight percent of theory yield) of a clear liquid hiving a IL 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 l-phenyl-3-n-heρtyl-2-S-ethyl isothiourea -f- toluene-2,4-diisocyanate

The equipment was the same as used in Example 26.

>0 2.78 g (0.01 mole) l-phenyl-3-n-heptyl-2-S-ethyl isothiourea in 35 ml of tetrahydrofuran were mixed xdth 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

1-5 refluxed for an additional hour to react all the isocyanate.

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The reaction mixture was vacuum evaporated to produce 4.1 g of a viscous, yellow liquid having a n_ 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-l-heptyl)-N ^t -n-heρtyl,n-octadecylcar- bamyl-2-S-ethyl isothiourea

The equipment was the same as in Example 26. 2.4 g

(0.007 mole) l-(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 _D 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 ^f -di-n-heptyl,S-ethyl isothiourea

3.0 g (0.01 mole) l,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 ^β 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_ 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 l,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 l,3-di-n-heρtyl-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 ng 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 l,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 10 g (0.01 mole succinic anhydride was substituted for the diglycolic anhydride. The reaction yield was 4.1 g of a semi-solid. Th product was identified as the title product by NMR spectra analysis. Compound No. 331 in Table I.

Example 44

Adduct of 1 mole l,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 formalde¬ hyde 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 l,3-di-n-heρtyl-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 an¬ hydride. The reaction yield was 4.3 g of a liquid having a n _D 30 of 1.4825. The product was identified as the title product by NMR spectra analysis. Compound No. 328 in Table I.

Table I

S-R,

R-N ^» C-N-R-,

I 1

^R 3

« ³⁰ or

Compound No, R R, R,

- ^C 7 ^H 15 ^"C 7 ^H 15 ^*"C 2 ^H 5 1.4760 I

00 I ,

Compound No, R Ri R, 30

~ ^C 7 ^H 15 -C ₇ H ₁₅ ^"C 2 ^H 5 1.4956

R,

0

-CNH y > CH ₃ -(CH ₂ ) _n -CH ₃

Cflζ ^NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ ~0

0 n average ^α 11 One of the reactants was Tergitol®^ 15-S-7 a product of Union Carbide Corporation in which the average ^" Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R Ri R, tip 30 or

~ ^C 7 ^H 15 -C ₆ H ₁₅ ^• C ₂ H ₅ 1.5021

n average » 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R

4 -C ₆ H ₁₅ ~ ^C 7 ^H 15 ^"C 2 ^H 5

5 ~ ^C 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ Thick oil

n average " 7.7 One of the reactants was Carbowax^ 400 a product of Union Carbide Corporatio in which the average Molecular Weight is 400 and n averages 7.7.

n„ 30 or

Compound No . R R, R, R. °C

^"C 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ 1.5254

8 5

- ^C 7 ^H 15 ^"C 7 ^H 15 -c ₂ n ₅ 1.523

~ ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

10 - ^C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ 1.5186

11 ^"C 7 ^H 15 ^"C 7 ^π 15 -C ₃ H ₇ 1.5188

n~ 30 o

Compound No. R R^ R, °C

13 ~ ^C 7 ¹ L5 -C ₇ H ₁₅ "C ₄ H ₉ • Q 1.518

0

14 - ^C 7 ^lI 15 - ^C 7 ⁿ 15 ^"C 5 ^H 11 -CNH-<Q> 1.514

15 -c ₇ ιι ₁₅ -c ₇ ιι ₁₅ 1.511

0

II

16 - ^C 7 ^π 15 - ^C 7 ⁿ 15 - _Cl H ₃ -GNU *0 1.525

0

II

17 ^"C 7 ^IT 15 ^"C 7 ^H 15 -ic ₄ n ₉ -CM *© 1.514

18 1.50

~ ^C 9 ^H 19 - ^C 8 ^TI 17 -C ₂ H ₅

20 ^"C 8 ^H 17 ~ ^C 8 ^H 17 ^■ C ₂ H ₅ 1.5175

21 1.5170

- ^C 7 ^H 15 ^"C 9 ^H 19 ~ ^C 2 ^H 5

22 -tC ₈ H ₁₇ - ^C 8 ^H 17 ^"C 2 ^H 5 1.5134

I

23 -C ₇ H ₁₅ ~ ^C 8 ^H 17 ~ ^C 2 ^H 5 -z -Q/ 1.5185 4

24 ^C 6 ^H 13 ^"c ιo ^H 2: -C ₂ H ₅ 1.5191

25 ^"C 8 ^H 17 ~ ^C 8 ^H 17 -C ₄ H ₉ -CNH-<g) 1.5135

O

26 -CgH ₁₇ -CgH ₁₇ ^"C 5 ^H 11 -C H-^> 1.5125

<-o

Compound n_ 30 or No . R R ₁ R, R °C

27 ^"C 6 ^H 13 -C ₉ H ₁₉ -C ₂ H ₅ ^• CNH 1.5179

0

II

28 1.51

~ ^C 6 ^H 13 ~ ^C 9 ^H 19 ^"C 5 ^H 11 -CNH 20

^■ Ό

O

II

29 -C ₇ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4750

0

30 ^"C 7 ^H 15 ^"C 7 ^H 15 ~ ^C 2 ^H 5 -CNHC ₈ H ₁₇ 1.4786

O

31 ^C 7 ^H 15 -C ₆ H ₁₅ -C ₂ H ₅ -CNHC ₆ H ₁₃ 1.4800

O

32 -C ₇ H ₁₅ -C ₇ H ₁₅ ^"C 2 ^H 5 •C H^)- 0C H _R 1.5180

Υ ^l 5

Compound No. R R,

33 ^"C 7 ^H 15 ~ ^C 7 ^H 15 ^■ C ₂ H ₅ 1.4970

R.

n average ^» 11 One of the reactants was Te gitol 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Cl

35 V 1.5245

^C 8 ^H 17 ^"C 8 ^H 17 ~ ^C 2 ^H 5 - ^CNH~

O CF ₃

36 1.4966

^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CNH-<g>

39 ^C 6 ^H 13 ~ ^C 6 ^H 13 -C ₂ H ₅ 1.5317

1.5215

0

43

~ ^C 8 ^H 17 - ^C 6 ^H 13 -C ₂ H ₅ -CNH-^^-0CH ₃ 1.5200

O

44

^"*C 6 ^H 13 ~ ^C 6 ^H 13 -C ₂ H ₅ -CNH - OCH 1.5261

0

45 II

^"C 8 ^H 17 ^"C 8 ^H 17 ~ ^C 2 ^H 5 -cm y--ocH, 1.5175

0 0

46 H ii

~ ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ ^■ CNHCH ₂ COC ₄ H ₉ 1.4770

49 -secCyH- _j ς 1.5230

50 -secC ₇ H-ιc -C ₈ H ₁₇ -C ₂ H ₅ -CNH-<^-0CH ₃ 1.5190

0

II

52 -C ₆ H ₁₅ -CNHC ₂ H ₅ 1.4830

~ ^C 7 ^H 15 -C ₂ H ₅

0

53 -C _y H ₁₅ -C ₇ H _{15 2} CH=CH ₂ 1.4871

^"C 2 ^H 5 -CNHCH

O

54 -C ₂ H ₅ -CNH-^> 1.5270

^"C 7 ^H 15 ^"C 7 ^H 15

Compound nj 3:0 or No. R R, R, R,

°C

55 ~ ^C 7 ^H 15 ₃ H _y -i 1.4765

O

II

56 —SeC >-tH-t c ^"C 7 ^H 15 ^"C 2 ^H 5 -CNH, 1.4768

O

II

57 -secC ₇ H-ι ~ ^C 8 ^H 17 -C ₂ H ₅ -CNH 1.5175

58 —SeCL»-fH_ι '■ϊ ~ ^C 7 ^H 15 ~ ^C 2 ^H 5

0

59 -secC ₇ H ₁₅ ~ ^C 7 ^H 15 -C ₂ H ₅ -CN1 ^■ ©- OCH. 1.5190

Compound No. R Rn R, R, °C

62 -secC ₇ H- _j ^"C 7 ^H 15 ^■ C ₂ H ₅ 1.5237

63 -C ₇ H ₁₅ -C ₆ H ₁₅ 1.5242

~ ^C 2 ^H 5

0 O ϊl II

64 ^•C 7 ^H 15 ^"C 7 ^H 15 -C ₂ Hιj -CNHCH ₂ CNHCH ₂ CH, ₂ OH 1.48

0 tl

65 ^• secC ₇ H- _j c -secC ₇ Hτc ^"G 2 ^H 5 -CNH ₂ 1.4725

0

66 secC ₇ H ₁₅ -C ₆ H ₁₃ -C ₂ H ₅ -C H-<^- OCH ₃ 1.5210

0 ll JC1

67 -secC ₇ H ₁₅ -C ₆ H ₁₃ ^"C 2 ^H 5 -CNH-<£) Soft so

Compound n _D 30 or

No. R Rn R, R. °C

0

/I

69 -secC ₈ H ₁₇ -secC ₇ H ₁₅ -C ₂ H ₅ -CNH 1.5125

0 II

70 ^■ secC _g H^ ₇ -secC ₇ H ₁₅ ~ ^C 2 ^H 5 -CNH 1.5115

71 •secC ₈ H ₁₇ -secCJtt- _j e 1.5205

0

72 ' ecCαti-i -. — sec -itl-i t -C ₂ 1 -CNHC ₁₈ H ₃₇ 1.4720

0

73 ^C 7 ^H 15 -C ₆ H ₁₅ -C ₂ H ₅ -C H-^)-o-^ . 1.5390 O 74 C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CNHC ₁₂ H ₂₅ 1.4765

0 Cl

78 ^• secC Hι c - ^C 8 ^H 17 -c _Λ -C H-ζy 1.5280

O

79 ^• secC H-jc " ^c 8 7 ~^1**3 -CNHC ₁₈ H ₃₇ 1.4750

80 •secC H-ι c

1.5305

81 ^■ secC ₇ Hιc

82 •secC Hir -secC H ₁₅ -C ₂ H ₅ 1.5240

₁₈ H ₃₇ 1.4740

Compound n 30 or No. R R^ R, R, ^V C

84 -secC H-jc - ^C 8 ^H 1 ~ ^C 2 ^H 5 -Cl NH- - Cl 1.5295

85 -2-ethylr -2-ethyl- -C ₂ H ₅ hexyl hexyl

85 - njj° or °C - 1. .55220011

0

86 -sec-C ₇ H ₁₅ -C ₈ H ₁₇ ^"G 2 ^H 5 -CNHC ₁₈ H ₃₇ -n 1.4740

88 ^"tC 8 ^H 17 - ^C 8 ^H 17 ^"C 1 ^H 3 1.5276

-C ₁₈ H ₃₇ 1.4772

.91 -secC ₇ H _j e ^"C 8 ^H 17 -C ₂ H ₅

91 - nj*° or °C - 1.5170

92 -secC-yH-i c "*SΘCl-_*" 1*1 c ~ ^C 1 ^H 3

93 ^■ 2-ethyl- -2-ethyl- -C ₂ H ₅ 1.5258 hexyl hexyl o

94 -2-ethyl- -2-e hyl- -C ₂ H ₅ ^• CNH-C ₁₈ -H ₃₇ 1.4760 hexyl hexyl

95 2-ethyl- -2-e hyl- -C ₂ H ₅ 1.5306 hexyl hexyl

97 -2-ethyl- -C ₇ H ₁₅ hexyl ^"C 2 ^H 5

98 — secϋ- _j til-i c -secC ₇ H-. c -C ₂ H ₅

0

II

101 -2-ethyl- ^■ CNH H^)-OCH ₃ I- ^{5000 "G} 7 ^H 15 ^rC 2 ^H 5 hexyl

102 - n^° or °C - 1.5226 D

CHq

^C 7 ^H 15

104 - n _D 30 o „r - 1.5190

105 -tC ₈ H ₁₇ -2-ethyl ^■ C ₂ H ₅ hexyl

2-ethylhexyl

0 u Cl

106 -2 -ethyl¬ -C ₇ H ₁₅ ^• C ₂ H ₅ -CNH / W 1.5277 hexyl

0 ιι

107 -2-ethyl- -C ₇ H ₁₅ —L<« _j Hc -C HC ₁₈ H ₃₇ 1.4775 hexyl

108 -secC ₇ H ₁₅ ^"C 8 ^H 17 -CH ₂ SCH ₃ 1.5255

0

109 -2-ethyl- -C ₇ H ₁₅ -C ₃ H ₇ -CNH ^-C ^{7 N} )-<OCH 1.5200 hexyl

110 -2-ethyl- ^"C 7 ^H 15 -C ₃ H ₇ X. • J jJ / hexyl

0

111 -2-ethyl- -C ₆ H ₁₅ -C ₃ H _? -CNHC ₁₈ H ₃₇ 1.4772 hexyl

C ₃ H ₇ 1.5237

112 -2-ethyl- - hexyl ^"*C 7 ^H 15

C ₁₈ H _3? 1.4744

0

114 -2-ethyl- ^• C ₈ H ₁₇ -C ₂ H ₅ -CNH hexyl ^■ Q-

2-ethylhexyl

114 -n{*° or °C - 1.5170

115 -secC ₇ H ₁₅ ^■C 6 ^H 13 -C ₂ H ₅

^C 6 ^H 13

117 2-ethyl -C ₂ H ₅

^"C 6 ^H 13 hexyl

2-ethyIhexy

118 - n^° or °C - 1.5190

0

119 -2-βthyl- H ₃₇ hexyl ^"C 8 ^H 17 ^"C 2 ^H 5 -CNHC ₁₈ 1.4765

120 -tC _g H _l7 • 2-e thy 1- -C ₃ H ₇ hexyl

125 ~ ^C 7 ^H 15 -2-ethyl -C ₂ H ₅ hexyl

125 - nj 3j0 ^u or °C - 1.5393

0

126 ^■ "S βCLi- _j iTi c ~ ^C 8 ^H 17 -C ₂ H ₅ -£NHC ₁₂ H ₂₅ 1.4763

127 -secC ₇ H _l5 -secCyH _j c ~ ^C 2 ^H 5

127 - n ³⁰ or °C - 1.5310

128 -2-ethyl- -2-ethyl- -C ₂ H ₅ hexyl hexyl

128 - n ³⁰ or °C - 1.5340

130 -tC ₈ H ₁₇ -2-ethyl- -C ₂ H ₅ 1.5271 hexyl

0

131 -tC ₈ H ₁₇ -2-ethyl- hexyl ^"C 2 ^H 5 ^■ CNHC ₁₈ H ₃₇ 1.4785

132 -tC ₈ H ₁₇ -2-ethyl- -C ₃ H ₇ 1.5150 hexyl

133 -secC ₇ H- _j c - ^C 6 ^H 13 -C ₂ H ₅

^C 6 ^H 13

133 -n ³⁰ or °C - 1.5345

134 -

135

I

135 - I

136

138 -secC ₇ H _j e ~ ^C 6 ^H 13 -CH ₂ SCH ₃

138 - nj° or °C - 1.5344

140 - n 30 D or °C - 1.5293

1.5295

1.5317

144 -secC ₇ H ₁₅

145 — secj- _jf H-i -

I

I

145 - n ³⁰ or °C - 1.5225

146 HC ₁₈ H ₃₇ 1.5140

147 -2-ethyl- hexyl

^C 8 ^H 17

148 - np° or °C - 1.57357

1.5785

151 - n^° or °C - 1.5737

Compound n„ 30 o ^• r No . R Rn R, R. °C

152 "SQClc Hi c ~ ^C 8 ^H 17 -C ₃ H ₇

30

152 or °C 1.5134

^

O

II

153 -secC ₇ H ₁₅ -C ₈ H ₁₇ -C ₃ H _? -CNHC ₁₈ H ₃₇ 1.4746

O

II

154 -secC ₇ H ₁₅ -C ₈ H ₁₇ -C ₃ H ₇ ^• CNH- Cl 1.5200

O

155 - ^"C 7 ^H 15 ~ ^G 2 ^H 5 ^■ CNHC ₁₈ H ₃₇ 1.5061

₁₈ H ₃₇ 1.5165

Compound 30 No. n _D or

R R, R, .

°C

0

159 II

^"C 8 ^H 17 (CH ₂ ) ₆ C1 -C ₂ H ₅ ^• CNHC ₁₈ H ₃₇ 1.4876

0

160 - -C ₇ H ₁₅ -C ₂ H ₅ CNH *-®V_>- ^~ OCH, 1.5743

161 (C ₆ H ₅ ), ₂ CH- ^"C 7 ^H 15 ^■C 2 ^H 5

161 - np° or °C - 1.5760

0

162 -secC ₇ H^ ₅ ι

^"C 12 ^H 25 -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4736

ound n _D 30

Comp or No. R ^R 3 °C 0

163 -C ₈ H ₁₇ (CH ₂ )2 ^SC 5Hιι -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4850

0

164 -secC ₇ H- _j c -2-ethyl- -iC H ₉ -CNHC ₁₈ H ₃₇ 1.4754 hexyl

0

165 ~ ^C 7 ^H 15 CH ₂ ^» C _H CH ₂ - ~ ^C 2 ^H 5 -CNHC ₁₈ H ₃₇ 1.4810

0

166 - ^C 7 ^H 15 (CH^OCH _j -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4773

0 .

167 -2-ethyl- -C H ₇ -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4746 hexyl O(CH ₂ ) ₃ ^> '

0 0

168 ^**C 8 ^H 17 (CH ₂ ) ₆ OCNHCH ₃ - -CNH- A 1.5244

~ ^G 2 ^H 5

Compound n _D or

No. R

^R 3 °C 0

170 -2-ethyl- hexyl -o -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4836

171 -secC H,c -2-ethyl- 735 hexyl ^"C 7 ^H 15 1.4

0

172 -secC ₇ H- _j c

~ ^C 9 ^H 19 -C ₂ H ₅ -I:NHC ₁₈ H ₃₇ 1.4740

0

173 0 ^CH 2- ~ ^C 7 ^H 15 ~ ^C 2 ^H 5 -CNHC ₁₈ H ₃₇ 1.4845

0

174 -secC ₇ H ₁₅ ^C H ₂ -<2> -C ₂ H ₅ -^NHC ₁₈ H ₃₇ 1.4930

0

175 -2-ethyl- (CH ₂ ) ₃ C1- -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4950 hexyl

0

176 ^"C 7 ^H 15 (CH ₂ ) ₃ 0CH ₃ - ^"C 5 ^H 11 -έ _N HC ₁₈ H ₃₇ 1.4755

O II

177 ΛΛAΛ -C ₅ H _n -C HC ₁₈ H ₃₇ 1.4750

^"C 7 ^H 15

O

178 ΛΛAΛ •C ₇ H ₁₅ -C ₂ H ₅ ^• CNHC ₁₈ H ₃₇ 1.4760

^G 12 ^H 25

₅ 2-e thy Ih

180 - n^° or °C - 1.5295

3

r ci 1.5825

O *C HC ₁₈ H ₃₇ 1.4765

Clio

« «___

Compound n _n or No. R

^ ^R 3 °C

186 -C ₈ H ₁₇ -™2-Q -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4890

O

187 -2-ethyl- -2-e hy1- -CH ₂ CH-CH ₂ —CNHC-ioH»» ₇ 1.4800 hexyl hexyl

O

188 -C ₇ H ₁₅ -(CH ₂ ) ₃ N(C ₂ H ₅ ) 2 -C ₂ H ₅ -CNHC ₁₈ H ₃₇ 1.4780

O

; 189 -2-e hyl- -2-ethyl- -CNHC ₁₈ H ₃₇ 1.4757 hexyl hexyl ^"C 3 ^H 7

0

190 -secC ₇ H^c - ^C 8 ^H 17 - ^CH 2-© -CNHC ₁₈ H ₃₇ 1.4924

191 ~S ^β Cϋ-ιHι 1.5210

"Gntlc 1.5386

194 yl-0-(CH ₂ ) ₃ - -C ₃ H ₇ -C ₂ H ₅ 1.5250

0

II

195 ^• secC ₇ Hι c -2-ethyl- -CNH Cl hexyl ^"iC 3 ^H 7 "-Or ¹ 1.5195

196 2-ethyl- hexyl -o -C ₂ H ₅

0

II

197 secC ₇ H^c -2-ethyl- -CNH hexyl ^"C 7 ^H 15 ty 1.5146

198 3βC(_>- lι*ι c ₁₈ H ₃₇ 1.4820

30

Compound No. R R ₃ °C

0 /

200 -C _y H ₁₅ -CH ₂ CH ₂ CCH ₃ 1.4543

~ ^C 7 ^H 15 ~ ^C 2 ^H 5

O

II

201 -C ₇ H ₁₅ -C ₂ H ₅ -S-CH., 1.4807

^"C 7 ^H 15 p

0

II

202 — C Hι- 1.4836

~ ^C 7 ^H 15 -C ₇ H ₁₅ — S

~ ^C 2 ^H 5 il ^{2 5}

O 0

203 ^"C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -s |l-c ιι ₇ 1.4805 < J / 0

0

205 -C ₂ H ₅ 152

~ ^C 7 ^H 15 ~ ^C 7 ^H 15. ^■ © 1.5

0

Compound _D 30 or No . R Rn R, R,

°C

207 -C ₇ H ₁₅

~ ^C 7 ^H 15 -C ₂ H ₅ - 0r - Cl 1.5207

O

208 - ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -S-<^-0CH, 1.5215

O

O

209 -C ₇ H ₁₅

^"C 7 ^H 15 -C ₂ H ₅ ^■ ?O ^~ N "O".2 1.5273 I

0 0 0 I

211 H ₃ -CH, 1.5559

212 H ₃ -CH. Dark oi

213

214

0

215 β ^~ -CH ₂ C0CH (CH ₃ ) ₂ -CH ₃ 1.5417

~ ^C 1 ^H 3

SCF.

Compound No. R R. R, n _D 30 or

°C

216 ^"C 7 ^H 15 . ~ ^C 7 ^H 15 -C ₂ H ₅ 1.5785

R,

n average ^» 6.2 One of the reactants was Carbowax^ 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound No. R Rn R. n _D 30 or

°C

217 ^"C 6 ^H 13 ^"C 6 ^H 13 ^"C 2 ^H 5 1.5838

R,

n average - 6.2 One of the reactants was Carbowaslr 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound No, R Ri R, n _D 30 or

°C

218 ~ ^C 6 ^H 13 ^"C 8 ^H 17 -C ₂ H ₅ 1.5800

R,

NHC-0CH ₂ CH ₂ (0CH ₂ CH ₂ ) _n 0CH ₃ 0

n average ^β 6.2 One of the reactants was 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound No . R Ϊ R, n _n 30 or

°C

219 ^"C 7 ^H 15 ~ ^C 7 ^H 15 "Cntlc 1.5710

R.

0 I v U I n average ^m 11 One of the reactants was Tergitol !®^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R Rn R, 30 °D ^or

220 -CgH ₁₇ ^"'C 8 ^U 17 ^"C 2 ^H 5 1.5700

R,

I

I n average 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R R^ ^ •

221 " ^C 8 ^H 17 ~ ^C 6 ^H 13 ~ ^C 2 ^H 5 1.5680

R ₃

n average » 11 One of the reactants was Tergitor^ 15-S -7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R R, R, 30 "D ^or °C

222 ~ ^C 6 ^H 13 ^"C 6 ^H 13 -C ₂ H ₅ 1.5720

R,

n average 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R R-^ ₂ n _β or o » ___.

223 ~ ^C 6 ^H 13 " ^C 8 ^H 17 ~ ^C 2 ^H 5 1.5746

R ₃

I v x I

n average ^■» 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R Ri R, 30 °D ^or °C

224 -C ₈ H ₁₇ -C ₈ H ₁₇ -C ₂ H ₅ 1.5726

R.

n average ^β 11 One of the reactants was Tergitol**- 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

225 n .30 D or °C - 1.4930

0

226 •C ₇ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ -CNH-^)— (0CH ₂ CH ₂ ) ₂ 0C ₂ H,

v v

.30 I

227 - njj" or °C - 1.4885

?

228 H ₅ -CNH<Qμ(0CH ₂ CH ₂ ) ₂ 0C ₂ H _f

^"C 8 ^H 17 ^"C 6 ^H 13 -C ₂

230 -tC ₈ H _1? ^*"C 8 ^H 17 ^• C ₂ H ₅ -P(OC ₃ H ₇ ) ₂ 1.5460

233 ^tc 8 ^H 17 -C ₈ H ₁₇ -C ₂ H ₅ CH ₃ 1.4913

234 ^tC 8 ^H l7 ^*"C 8 ^H 17 ~ ^C 2 ^H 5

235 ^■ tC ₈ H ₁₇ ^"C 8 ^H 17 -C ₂ H ₅ 1.4863

0

H

240 -tC ₈ H _1? ~ ^C 6 ^H 13 -C ₂ H ₅ -CNH ^ OCH ₃ 1.5063

0 I

241 -CNH~(^-OCH ₃ 1.5215 ^tc 8 ^H 17 ^"C 7 ^H 15 -C ₂ H ₅

0

II

242 ^tc 8 ^H 17 ^"C 7 ^H 15 -C ₂ H ₅ -c NHHQ> Crude soli

1.5033

1.5044

0

II

246 ^tC 8 ^H 17 ^"C 7 ^H 15 -C ₂ H ₅ ^• CNH 1.4923

^■ Ό- CH.

0 ιi -0CH

247 ^• tC ₈ H ₁₇ ^"C 7 ^H 15 -C ₂ H ₅ -CNH J 1.4990

248 ^• tC ₈ H ₁₇ -C ₇ H ₁₅ -C ₂ H ₅

249 ^C 8 ^H 17 ~ ^C 4 ^H 9 -C ₂ H ₅ 1.5140

i? ^- Cl

250 ^• tC ₈ H ₁₇ ~ ^C 4 ^H 9 -C ₂ H ₅ -C H- 1.5135

0

254 -tC ₈ H ₁₇ -C ₄ H ₉ -C ₂ H ₅ -CNH-^)-OCH ₃ Crude soli

0

255 -tC ₈ H ₁₇ -C ₂ H ₅ -C H^ 1.4953

^"C 4 ^H 9

256 Cl 1.4953

^"tC 8 ^H 17 ~ ^C 4 ^H 9 -iC H ₉ iφ-

0

257 -tC ₈ H ₁₇ "iC ₄ H ₉

^**C 4 ^H 9 4m 1.5078

Compound No. R

259 -tC ₈ H ₁₇ -C ₄ H ₉ -iC ₃ H ₇

0

260 -C ₇ H ₁₅ ~ ^C 1 ^H 3 -C ₂ H ₅ -CNK ^- CH ₃ 1.5240

261 ^"C 7 ^H 15 ^"C 7 ^H 15 ^"C 2 ^H 5 - CH ₂ S (0C ₂ H ₅ ) 1.5060

0 S

262 CCH ₂ SP(0CH ₃ ) ₂ 1.5100 -

^"C 7 ^H 15 ~ ^C 7 ^H 15 ~ ^C 2 ^H 5 - !

Compound No. R Ri R n*> or

°C

263 ~ ^C 7 ^H 15 ~ ^C 7 ^H 15 ~ ^C 2 ^H 5 1.5030

R,

NHC-0CH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OCH ₃ 0

n average ~ 6,2 One of the reactants was a product of Union Carbide Corporation in which the average Molecular Weight ia 350 and n averages 6.2

Compound No , R Ri R, rip 30 or

264 ^"C 6 ^H 13 -C ₈ H ₁₇ -C ₂ H ₅ 1.4960

R.

(6) n average • ^» 11 One of the reactants was Tergitol*^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R Ri R, « ³⁰ or

265 ~ ^C 8 ^H 17 ^"*C 8 ^H 17 -C ₂ H ₅ 1.4942

R,

n average ^β 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R Ri R, r 30 or

266 ^: 6 ^H l3 ^"C 6 ^H 13 -C ₂ H ₅ 1.4955

R,

0

266 -CNH~< CH ₃ - (CH ₂ ) _n -CH ₃

CH ₃

n average ^a 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R

267 ~ ^c 6 ^H l3 ~ ^C 8 ^H 17 -C ₂ H ₅ 1.5025

R,

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OCH ₃ I 0 O vθ

I

n average ^» 6.2 One of the reactants was Carbowax^ 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound No, R i R, n30 D or

268 ~ ^C 8 ^H 17 ^"C 8 ^H 17 -C ₂ H ₅ 1.5005

R.

NHC-0CH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OCH ₃ 0 o

I n average - 6.2 One of the reactants was Carbowax^ 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound No. R

269 ^"C 6 ^H 13 ^*C 6 ^H 13 -C ₂ H ₅ 1.5065

R,

NHC-0CH ₂ CH ₂ (0CH ₂ CH ₂ ) _n 0CH ₃ 0

n average - 6.2 One of the reactants was Carbowax^ 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

271 ^"C 8 ^H 17 ^"C 8 ^H 17 ^■ C ₂ H ₅ - 9CNH-T ΓΛV- CH ₃ 1.5166

O

272 ^*C 8 ^H 17 ^*C 6 ^H 13 -C ₂ H ₅ -C H^)— CH ₃ 1.5200

273 •C ₈ H ₁₇ ^*C 6 ^H 13 ~ ^C 2 ^H 5

O Cl

II

274 ^"C 8 ^H 17 ^"C 6 ^tt 13 -C ₂ H ₅ -CNH rH 1.5240

0

275 ^"C 8 ^H 17 ^"C 6 ^H 13 ~ ^C 2 ^H 5 - ^m 1.5205

J—I

280 ^{5 G} 8 ^H 17 ^C 7 ^H 15 ^"C 2 ^H 5 1.585

281 -C ₂ H ₅ .4974

^C 8 ^H 17 ^"C 7 ^H 15 &" ^! 1

285 ^C 8 ^H 17 ~ ^C 6 ^H 13 -iC ₃ H ₇ 1.5242

286 ^C 8 ^H 17 -C ₇ H ₁₅ -C ₂ Hc 1.5228

0

287 ^C 8 ^H 17 ~ ^C 6 ^H 13 -C ₂ H ₅ -C HHζ 1.5244

1

288 ^C 8 ^H 17 ^"C 6 ^H 13 ^"iC 3 ^H 7 1.5286

Compound 30 No. R ^or °C

290 ~ ^C 8 ^H 17 ^"C 6 ^H 13 -C ₂ H ₅ 1.5331

O 0 ^S , ^C 3 ⁿ 7~ ^±

291 ~ ^C 8 ^H 17 ~ ^C 6 ^H 13 -iC ₃ H _? -CNH-rΛ-NHC-N-C

CH ₃ ^NC 8 ^H 17

291 - njj ⁰ or °C - 1 1..55220011

292 - njj° or °C - 1.5258

^C 8 ^H 17

I

^• rt

0 0 SC ₂ H ₅ I ι» II

294 -C ₈ H ₁₇ ~ ^C 6 ^H 13 ^*C 2 ^H 5 ^• CNH-t^ - NHC-N-C

<*i CH. NC ₈ H _ly

^C 6 ^H 13

^C 6 ^H 13

^C 6 ^H 13 xj I

296 - n^° or °C - 1.5182

297 ^"C 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ ^■ SCCl. 1.5084

298 -SCC1 ₂ CFC1 ₂ 1.5091

^"C 7 ^H 15 ^"C 7 ^H 15 ~ ^C 2 ^H 5

301 -2-ethyl- •2-ethyl- -SCC1. 1.5060 hexyl hexyl ^*C 2 ^H 5

302 ^C 7 ^H 15 -C-iH-j _f - •C ₂ H ₅ 1.5580

^C 4 ^H 9

303 - 30 or °C - 1.5245

0

304 -C ₈ H ₁₇ -3,7-dimethyl- -C ₀ H _ς •έNHC ₁₂ H ₂₅ 1.4882 2,6-octadienyl ^l -*

CH.

C ₂ H ₅

V

307

308 2-ethyIhexyl

308 - jj° or °C - 1.5029

309 -2-ethyl- -2-ethyl- •SCH ₂ CH ₂ hexyl hexyl

2-ethylhex

309 -

310 o

2-ethylhexyl I

0 0

|l I'

311 -C ₇ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ -CCH ₂ CCH ₃

0

00

314 ^"C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CCNHC ₃ H ₇ -i Low-melting material

00

|l II

315 - ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CCNHCH CH=CH ₉ Low-melting * ^■ material

0 il Θ θ

316 ^C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ -CCH ₂ N(C ₂ H ₅ 31 Semi-

>3 ⁽ solid

317 ^C 7 ^H 15 ~ ^C 7 ^H 15 ~ ^C 2 ^H 5

318 ic

^C 7 ^π 15 ~ ^C 7 ^H 15 -C ₂ H ₅ - (CH ₂ ) ₃ Hygroscop

319 5425

^C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ 1.

OH

322

~ ^G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CHCH ^» CH, 1.4630

323 -C ₆ H ₁₅

^■C 7 ^H 15 -C ₂ H ₅ -CH ₂ 0H Semi- solid

OH I

324 ^'C 7 ^H 15 ^*C 7 ^H 15 -C ₂ H ₅ -CH-CHO 1.4513 '

I

OH

I

328 -C ₇ H ₁₅ ~ ^C 7 ^H 15 -c ₂ ιι ₅ -CH- ^/ 0CH„ 1.4825

0

329 -C ₆ H ₁₅ ^"C 7 ⁿ i5 -C ₂ H ₅ -C , ■COOH Semi-solid

330 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CCH∞CHCOOH No line

0 t t

331 -C ₇ H ⁷ 15 ~ ^C 7 ^H 15 -C ₂ H ₅ ^• CCH ₂ CH ₂ COOH Semi- solid"

0

II

332 ~ ^C 7 ^H 15 ^"C 7 ^Π 15 ^• C ₂ H ₅ ^■ CCHC1, 1.4729

/ ^" 0

| l

333 ^"C 7 ^H 15 ^"C 7 ^1! 15 ^■ C ₂ H ₅ -CCH=CHCOO H ₂ T 1 ( / CII ₂ CH ₂ OII) ₂

335 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -I CH ^» CH, 1.4672

336 ^"C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 1.4856

o Θ ® I l- ¹

338 ^"C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ •CCH ₂ OCH ₂ COO • HNEt ₃ 1.4560 •P-

339 -C ₆ H ₁₅ ^'C 7 ^H 15 -C ₂ H ₅

339 - n^ ⁰ or °C - 1.4870

0

II

343 ^"C 7 ^H 15 - ^C 7 ^H 15 -C ₂ H ₅ -SNH ₂ 1.4670

344 -C ₇ H ₁₅ - ^C 7 ^H 15 -C ₂ H ₅ 1.4874

346 ^C 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ -S0 ₃ CH ₃ 1.4325

347 ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -S0 ₂ NHC H ₉ 1.5264

(0H) ₂ Glass

349 -C ₇ H ₁₅ -C ₇ H ₁₅ ~ ^C 2 ^H 5 -S0 ₂ N(C ₂ H ₅ ) ₂ 1.4356

0

350 ^"G 7 ^H 15 ^*"C 7 ^H 15 -C ₂ H ₅ ^• CCHoOCH, 1.5140

O Q Θ

I"

351 -C ₇ H ₁₅ ^""C 7 ^H 15 -C ₂ H ₅ -CCH ₂ CH ₂ C00 H N \ ^ N ^■ H

1.5464

H _/ SH

354 Stench

^"G 7 ^H 15 - ^G 7 ^H 15 -C ₂ H ₅ SH

Compound « n _D ^{3 0} « ofr

No. R , R, R- °C

0

II

355 - ^G 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ -C(CH ₂ ) ₅ 0H 1.4600

356 -C ₇ H ₁₅ -C ₇ H ₁₅ - ^G 2 ^H 5

356 - n ° or °C - 1.4467

OH

357 -C ₇ H ₁₅ ^"G 7 ^H 15 ^•G 2 ^H 5 -^ ^N"G - ^SC 2 ^H 5 1.5730

^H ° ^N - ^G 7 ^H 15 I t- ^{1 C} 7 ^H 15 xj

I

359 880

^"G 7 ^H 15 ~ ^C 7 ^H 15 C ₂ H ₅ -SCC1. 1.4

360 ~ ^C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ -

361 ~C ₇ H ₁₅ ^"G 7 ^H 15 ^*"C 2 ^H 5 -C(CH ₂ ) ₃ COH 1.4670

0 0

362 -C ₇ H ₁₅ ~ ^C 7 ^H 15 ~ ^C 2 ^H 5 -CCC1-CC1C0H 1.4780

0

363 -C ₆ H ₁₅ - ^G 7 ^H 15 -C ₂ H ₅ -CHOCNΪH^ 1.4990

CH ^« CHCH

0 C1 00 I

364 ^"G 7 ^H 15 ^*G 7 ^H 15 -C ₂ H ₅ -CHOCNH *-® , 1.4970

CH-CHCH.

365 ^"G 7 ^H 15 ^*G 7 ^H 15 - ^G 2 ^H 5 -CH ₂ 0CNH-^ 1.4915

366 ~ ^C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅

•'" ft @

368 ~ ^C 7 ^H 15 ^**C 7 ^lI 15 -C ₂ H ₅ -CC0 ^y • Al Semi-soli ι 1

369 - n^° or °C - 1.4620

00

370 ^"G 7 ^H 15 ~ ^C 7 ^H 15 - ^G 2 ^H 5 •CC0 Ca 1/2

373 -C ₇ H ₁₅

^"C 7 ^H 15 -C ₂ H ₅ -S0 ₃ . H <^ 1.4630

IHN )

374 - n^° or °C - Semi-solid

0

375 -2-ethyl- -2-ethyl- -C ₂ H ₅ -CCHCl 1.4664 hexyl hexyl

0 I

II

376 -secC ₇ H ₁₅ 1.4666

- ^C 6 ^H 13 -C ₂ H ₅ -CCHCl

0 ιl

377 ^• secC ₇ H-^ ₅ ^"G 8 ^H 17 -C ₂ H ₅ -CCHCl 1.4633

Compound n _n 30 or

No . R R^ R, R,

β _/ SH

380 -2-ethyl- -2-ethyl- -C ₂ H ₅ -P 1.5487 hexyl hexyl SH

S

II .SH

381 ^• secC ₇ H^c 1.5638

^"G 7 ^H 15 -C ₂ H ₅ -P

\ SH

rt

383 1.4612

0 0

II II

384 -2-ethyl- ^■ 2-ethyl- ^■ C ₂ H ₅ -CCH ₂ CH ₂ COH 1.4653 hexyl hexyl

0 0

Compound No , R Ri R, n _D 30 or

°C

387 ^"G 7 ^H 15 -C ₆ H ₁₅ -C ₂ H ₅ Thick oil

R,

n average ^« =• 7.7 One of the reactants was Carbowaxr 400 a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No, R

388 ^"C 7 ^H 15 ^"C 7 ^H 15 •C ₂ H ₅ 1.5021

R,

t C I

n average » 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No. R Ri R, R, n _D 30 or

°C

389 -C ₆ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

389 - np° or °C - 1.5000

390 -C ₇ H ₁₅ " ^G 7 ^H 15 ~ ^C 2 ^H 5 -(CH ₂ ) ₈ -C-Cl

Compound No, R R, R, 30 % ^or °C

391 ^"C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅

R,

O ^CH 3-( ^{C I} 2>n ^"CH 3

391 -(CH ₂ ) ₈ -(!-0CH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ ~0

I t n average ∞ 11 One of the reactants was Tergitor^ 15-S-7 I a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No , R Ri R, H _j 3.0 or

°C

392 ^"G 7 ^H 15 ~ ^G 7 ^H 15 -C ₂ H ₅

R.

392 - (CH ₂ ) ₈ -C-0CH ₂ CH ₂ (0CH ₂ CH ₂ ) _n 0H

n average ^» 7.7 One of the reactants was a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No, R R, *3 • _D 30 or

°C

0

393 ~ ^C 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ -0-CH ₂ CH ₂ OCCl

Compound No. R Ri R, 30 "D ^or

394 -C ₆ H ₁₅ ~ ^G 7 ^H 15 25

R-

0

II

394 -0-CH ₂ CH ₂ OC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OH

to

00 I n average ^ 7.7 One of the reactants was C rbo ax^ 400 a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No , R Ri R, n _D 30 or

395 ^""C 7 ^H 15 ^**G 7 ^H 15 •C ₂ H ₅

R,

0 CH ₃ - (CH ₂ ) _n -CH ₃

395 -0-CH ₂ CH ₂ 0C-0CH ₂ CH ₂ (0CH ₂ CH ₂ ) g-0

n average ^β 11 One of the reactants was Tergitol^ 15-S-7 c a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R

Compound No, R R^ R, 30 "D ^or

397 ~ ^C 7 ^H 15 ~ ^C 7 ^H 15 ^"G 2 ^H 5

R,

397 -Q NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) OH 0

n average ^« 7.7 One of the reactants was Carbowax J8^> 400 a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No, R Ri R, up30 or

398 ^"C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅

R-

n average ■= 11 One of the reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No, R Ri R n _n 30 or

°C

399 ^■C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

n average ^α 7.7 One of the reactants was Carbowax^ 400 a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No. R

400 - ^G 7 ^H 15 - ^G 7 ^H 15 ^■G 2 ^H 5 -NH-(CH ₂ ) ₆ NC0

401 - n^° or °C

402 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ -NH(CH ₂ )

0

II

403

~ ^C 7 ^H _L5 - ^G 7 ^H 15 -C ₂ H ₅ -NH(CH ₂ ) ₆ NHC(CH ₂ ) _l;L CH ₃

Compound No , R Ri R, 30 ^or

404 ~ ^C 7 ^H 15 ^■ C ₇ H ₁₅ -C ₂ H ₅

R,

O

I'

404 -NH(CH ₂ ) ₆ NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) OH

I n average ^« 7.7 One of the reactants was Carbowax ¹ ^ 400 I a product of Union Carbide Corporation in which the average Molecular Weight is 400 and n averages 7.7.

Compound No . R R. R, „30 _or

°c

405 ~ ^G 7 ^H 15 - ^G 7 ^H 15 -C ₂ H ₅

R,

0 CH ₃ - (CH ₂ ) _n -CH ₃

II

405 -NH(CH ₂ ) ₆ NϊϊC-0CH ₂ CH ₂ (0CH ₂ CH ₂ ) _fi -0

I

n average 11 One of tlie reactants was Tergitol^ 15-S-7 a product of Union Carbide Corporation in which the average Molecular Weight is 508 and n equals 9-13 and averages 11.

Compound No . R Ri R, R. n _D 30 or

°C

^G 7 ^H 15

406 - n ³⁰ or °C

0 0

II II

408 -C ₇ H ₁₅ -C ₇ H ₁₅ ~ ^G 2 ^H 5 -CNH(CH ₂ ) ₆ NHC-N-C-SC ₂ H ₅

N-C ₇ H ₁₅

^C 7 ^H 15

^G 7 ^H 15 4 00 I

410 ^"G 7 ^U 15 -C _y H ₁₅ -C ₂ H ₅ CH ₂ -<2-NHC- -C-SC ₂ H ₅ Liquid

N-C ₇ H ₁₅

^G 7 ^H 15

> 411 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

412 -C ₇ H ₁₅ -C ₇ H ₁₅ ~ ^C 2 ^H 5 Wax

413 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ Viscous liquid

-CH ₃

414 ^"G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

O o

415 x

^"C 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ ^• CNH I- -CH ₃ Wa

NHCNH(CH ₂ ) ₆ OH

416 -C ₇ H ₁₅ -C _y H ₁₅ -C ₂ H ₅

417 -C ₆ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

418 -C ₆ H ₁₅ -C _y H ₁₅ ^"G 2 ^H 5

419 ^"G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ Paste

421 IICOCH ₂ CH ₂ OC ₄ H ₉

0 iι

422 C ₆ H ₁₅ /

^"C 2 ^H 5 -CNH / CH, Viscous

^"C 7 ^H 15 - liquid

0

NHC(OCH ₂ CH ₂ ) ₂ OC H ₉

426 •C ₇ H ₁₅ Viscous

- ^G 7 ^H 15 ^"G 2 ^H 5 liquid

427 ^"G 7 ^H 15 ~ ^C 7 ^H 15 ~ ^G 2 ^H 5

r

428 -C ₆ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ Viscous liquid

Compound

No . R ^R 2

430 - -CC ₇ HH _115C - ~C ^G 7H ^H ,15 r - ^" C ^C 2H ^H 5*

431 ~- ^G C7 ^H H1,5,- ^" - ^G C7 ^H H1 ₁ 5 _t - --CC ₂ HH ₅ r 1.5312

NIICNHC ₃ H ₇

0

Ui

432 39 i

^"G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ CH, 1.53 I

0

NHCOCH ₂ CH ₂ Cl

433 "" ^C 7 ^H 15 ~ ^G 7 ^H 15 "" ^G 2 ^H 5

0

434 -C ₇ II ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CNH- - ₀ CH _{3 χ} Viscous liquid

NHCOCH z-e

0

435 H _ 1.5628

^"C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CNΪK ^N V-C

NHCOCH

Cl

437 ^•G ₇ ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

440 ^■ C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

441 •C ₇ H ₁₅ -C ₆ H ₁₅ 1.5524

444 ■C ₇ H ₁₅ -C _y H ₁₅ -C ₂ H ₅ Viscous liquid

445 -C ₇ H ₁₅ - ^G 7 ^H 15 ^'G 2 ^H 5

448 •C ₇ H ₁₅ Viscous liquid

449 ^"G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

452 ^"G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 1.5488

-^ N

453 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅

456 Viscous liquid

Ui

457 - ^G 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅

459 -C ₂ H ₅ Viscous

~ ^G 7 ^Π 15 ^"G 7 ^H 15 - 1CNH- / Λ_ CH ₃ liquid 0 NHC-O-(Cholesterol)

460 ^■ C ₇ H ₁₅ -CH-j r -C ₂ H ₅ Viscous liquid

462 -C ₇ H ₁₅ ~ ^C 7 ^H i5 -C2H5 1.5416

463 •c ₇ ιι ₁₅ Viscous

^"G 7 ^H 15 -C ₂ H ₅ liquid

464 Viscous liquid

cτ

Ό c

3 o • px CO vo VO o tf o fx. st ε st xt o o

OMPI

1.5378

473 ^C 7 ^H 15 - ^G 7 ^H 15 -C _Λ

475 ^"C 7 ^H 15 -C ₇ H ₁₅ ^"G 2 ^H 5 1.5124

476 •C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ 1.5172

H ^« CH,

477 ^"G 7 ^H 15 ~ ^G 7 ^H 15 -C ₂ H ₅

480 ^"C 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ 1.5233

481 •C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

O

483 - ^G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ Wax

484 ^'G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ Viscous liquid

I

0

485

^•G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CNH- C_ ™ ₃ Viscous liquid

NHCHHC ₄ H ₉ -seo

0

486 ^'C 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ Viscous liquid

Viscous li uid

488 ~ ^C 7 ^H 15 ~ ^C 7 ^H 15 -C ₂ H ₅ Viscous liquid

489 ^C 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ 1.550

^χ

0 I

490 ^"C 7 ^H 15 ^"C 7 ^H 15 -C ₂ H ₅ ^• CNH . CH, 1.5329

NHCN /- ^G 2 ^H 5

\

C ₂ H ₅

OMPI

496 ^"C 7 ^π 15 -C ₇ H ₁₅ -C ₂ H ₅

1.5280

NHCOC ₂ H ₅

498 ^'C 7 ^I! 15 ^*"G 7 ^H 15 -C ₂ H ₅

500 -C ₇ H ₁₅ ^"G 7 ^H 15 ^"G 2»5 1.5401

501 ~ ^G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅

502 •C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ ^/ — 0CH ₃

503 ^"C 7 ^H 15 ^"G 7 ^H 15 ~ ^G 2 ^H 5 Viscous / ° ^CI! 3 liquid

504 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

505 ^"G 7 ^H 15 ~ ^G 7 ^H 15 ^"G 2 ^H 5

I

506 •C ₇ H ₁₅ -C _y H ₁₅ -C ₂ H ₅ 1.552

508 -C ₇ H ₁₅ - ^G 7 ^H 15 -C ₂ H ₅

509 ₂ H ₅

^C 7 ^H 15 ^"G 7 ^H 15 -C

1.5494

512 ~ ^G 7 ^H 15 -C ₆ H ₁₅ ~ ^C 2 ^H 5 1.542

NHCNHC ₂ H ₅

NHCNHCH ₂ CH ₂ NHCNH

? - NHC-0

CH, N-C-SCH,. I II ^{2 5}

I ^N - ^G 7 ^H 15

515 -c ₇ π ₁₅ ^**G 7 ^H 15 -C ₂ H ₅ 1.5398

-N-C-SC ₂ H ₅

CH, N-C ₇ H ₁₅

^G 7 ^H 15

516 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅

517 ~ ^G 7 ^H 15 -C ₇ H ₁₅ •C ₂ H ₅ 1.5246

0

II

519 ~ ^C 7 ^H 15 - ^G 7 ^H 15 -C ₂ H ₅ -CNH -« CH,

NHCNH(CH ₂ )

519 - ~ 30 or °C - Very viscous liquid

520 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

30 520 - njj or °C - Viscous liquid

0

re m m re 2

CM CM

CM O O rt 1 I

m m

HH H H H 2 fx. fx. ι-4 O O i I I

525 -2-ethyl -2-ethyl- hexyl hexyl ^"G 2 ^H 5 1.5460

0

531 -2-ethyl- -2-ethyl- - H,- hexyl hexyl ^{Δ D} 1.5231

532 -2-ethyl- -2-ethyl- •C ₂ H ₅ hexyl hexyl

533 -2-ethyl- -2-ethyl- "C H_- hexyl hexyl 2 5

536 -2-ethyl- -2-ethyl- -CHH 1.5216 hexyl hexyl ^{z •} * 0

537 -2-ethyl- -2-ethyl- -C ₂ H ₅ 1.5294 hexyl hexyl ^GH 3

538 -2-ethyl- -2-ethyl- ~ ₂ H ₅ 1.5290 hexyl hexyl ^• I -4

O vθ I

0 ι» NHCNH,

539 -2-ethyl- - 2-e thy 1- •C ₂ H ₅ -CNH- // V 1.5309 hexyl hexyl CH,

540 -2-ethyl- ^• secCH-, ₅ •C ₂ H ₅ hexyl 1.5475

O

0 II

NHCOC

541 -2-ethyl- -secCHi -CHr -CNH-/ ⁷ 3H"7 1.5215 hexyl ' ^{1!> l} CI

543 ^*G 8 ^H 17 -secC ₇ H ₁₅ ~ ^C _? ^H 5 1.5234

0

544 •2-ethyl- ^• S Θ C _» - _j li K -C ₂ H ₅ 5275 i hexyl -CNIH X 1. CH 00 o

I

1.5298

CH ^,

549 ^"C 8 ^H 17 -secC ₇ H ₁₅ -C ₂ H ₅ 1.5455

1.5466

556 -C ₈ H ₁₇ ^• secCH _j c ^• C ₂ H ₅

557 -C ₈ H ₁₇ — sec - _jf H- _j c -C ₃ H _? 1.5180 secCH-i c

560 -2-ethyl- -2-ethyl- ~C ₃ H ₇ 1.5420 hexyl hexyl

561 -2-ethyl- -2-ethyl- hexyl hexyl ^"G 3 ^H 7

562 -2-ethyl- -2-e hyl- hexyl hexyl - ^C 3 ^H 7

566 •2-ethyl- ^■ secCH-,,- -C ₂ H ₅ 1.5278 hexyl

567 ^"G 8 ^H 17 •secCH- _j c ^"C 3 ^H 7

568 -secCH.. _c

^"G 8 ^H 17 -C ₃ H ₇ - 1.5270

569 •2-ethyl- ^■ secCH-. e •C ₂ H ₅ hexyl

570 -2-ethyl- ^• secCH, c •C ₂ H ₅ hex l

572 -2-ethyl- -secC ₇ H _1ς -CH,- ue hexyl e

578 -2-ethyl- -secCH-. ,- -CH«- 1.5330 hexyl ' ^1D

579 •2-ethyl- ^■ sec H _j r -C ₂ H ₅ 1.5305 00 hexyl I

580 -2-ethyl- ^■ secC r ^• C ₂ H ₅ hexyl

582 -2-ethyl- -secCH..ς -C H _ς 1.5415 hexyl ' ^{i> L D}

583 -2-ethyl- 1.5406 hexyl

584 -2-ethyl- -2-ethyl- -C ₂ H ₅ hexyl hexyl 2-ethyIhexyl

585 -2-ethyl- -2-ethyl- ~C ₂ H ₅ hexyl hexyl

593 NHC-0-/ ^~ Λ 1.5228 H,

secC ₇ H ₁₅

secCH, ,-

secCgH-, ₇

CgH- _{j 7} -sec

604 ^• secCH-je -secC B _j e ~ ^c ₂ ^ll 5 1.5178

-193-

fx. fx. m m

2 2 O 2 2

CO CM CM

CM O o O O fi I 1 I I

2-ethylhexyl

612 -secCH-, _* ~ ^C 2 ^H 5

613 ^■ secCHi c

sec-ClL ₇

615 1.514

616 -secC ₇ H ₅ -secC ₇ H ₁₅ " ^C 2 1.509

0 0 CH, rt

/ O Ui

617 ^• secC ₇ H ₁₅ -secC ₇ H ₁₅ ~ ^C 2 ^H 5 -CNH - NHCOCH 1.5164 I

CH,

CH ^,

₂ H ₅ 1.5128

CH

620 -secCH- _j c -secCH- _j c ~ ^C 2

621 -secCH- _j c -secCH- _j e " ^G 2 ^H 5 1.514

2-ethylhexyl

fi

3 o • st

CM m vo Px M ftO vO CM CM

82 vO o o

-^iREX^

-198-

Px m r _* (x.

2 2 O 2

CM 2 o CO

CM ? O O t o 1 o i

OMPI

II

632 -C ₇ H ₁₅ ~ ^G 7 ^H 15 — SCnHc -C-Tergitol 1.4488

0

II

633 •C ₇ H ₁₅ ^"G 7 ^H 15 -SC ₂ H ₅ •C-NHS0 ₂ -Tergitol 1.4564

634 ^"G 7 ^H 15 ~ ^C 7 ^H 15 -SC ₂ H ₅ 1.5583

I O

0 v I

II

635 ^• C ₇ H ₁₅

- ^G 7 ^H 15 -SC ₂ H ₅ ^• CNHS0 ₂ C1 62-77'

0 II

636 C ₇ H ₁₅ -C ₇ H ₁₅ -SC ₂ H ₅ ^• COC ₃ H ₇ -i 1.4425

Compound No, R Ri R, 30 ^or °C

638 ^G 7 ^H 15 -C ₇ H ₁₅ -SC ₂ H ₅ 1.5592

R,

0

//

638 -C-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OCH ₃

n average ^« * 6.2 One of the reactants was Carbowax^ 350 a product of Union Carbide Corporation in which the average Molecular Weight is 350 and n averages 6.2.

Compound 30 No. R Rn , R, "D ^or °C

639 ^"C 7 ^H 15 -C ₆ H ₁₅ •S C ₂ H ₅ - ?COC ₂ H ₅ 1.4841

0

640 II

•C ₇ H ₁₅ -C ₇ H ₁₅ -SCH ₂ CH ₂ OH -COC ₃ H ₇ -i Waxy semi- solid

641 -C ₇ H ₁₅ -C ₇ H ₁₅ ^• SCH ₂ CH ₂ OH

642 ^G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅

1.4621

0 C ₄ H ₉ -i

645 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ -CN 1.4538

C ₄ H ₉ -i

646 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CN s/ 1.4708

0

1/

647 ~ ^G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -C0C ₄ H ₉ -t 1.4412

I

I 0 t

I

648 ~ ^G 7 ^H 15 1.4553

^"G 7 ^H 15 -C ₂ H ₅ "-C0CH ₂ CsCH

0 0

Il II

649 -C ₂ H ₅ -C0CCH ₃ 1.4501

^"G 7 ^H 15 ^""G 7 ^H 15

0 CH ιι / 3

650 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ -CNHN 1.4654

CH ₃

•

0

1.4764

653 -C ₇ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ - 1.4563

O I t

654 ^•G 7 ^H 15 ~ ^G 7 ^H 15 -C ₂ H ₅ - ^C -N Q ⁾ 1.4689 U

I

655 ^"G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 1.4836

656 1.4660

Compound n _~ 30 or

No. R Rn R, R, D

°C

658 -C ₆ H ₁₅ ^"C 7 ^H 15 -C ₂ H ₅ ® 1.5095

0 NH II M

659 •C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CSC-NH, HC1 Glass

0 NH II ii

660 ^"G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ ^• CNHC-SC ₂ H ₅ 1.5209

661 ^"G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ • I

SCΛHC

0

662 -C 7H"15 -C 7H ⁿ l5 -C 2H"5 -C "NJI

1.4929

664 ~ ^G 7 ^H 15 ~ ^G 7 ^H 15 -C ₂ H ₅ -

664 - n^° or °C - 1.5228

0 0 ιι II

665 -2-ethyl- -2-ethyl- -C ₂ H ₅ -C-CH ₂ CH ₂ C0H • Et ₃ N 1.4899 hexyl hexyl

0 0 t n u

666 •2-ethyl- -C ₂ H ₅ -C(CH ₂ ) ₂ C0H Et ₃ 1.4879 ^" hexyl ^"C 8 ^H 17

0

667 secC ₇ H ₁₅ -C ₈ H ₁₇ ^■G 2 ^H 5 -CC ₃ H ₇ -i 1.4746

0

668 2-ethyl- -2-ethyl -C ₂ H ₅ .4930 hexyl hexyl - ^CH O 1

0

II

670 ^"G 7 ^H 15 - ^G 7 ^H 15 -C ₂ H ₅ -CCH, 1.4793

00

I II

671 -C ₇ H ₁₅

^G 7 ^H 15 -C ₂ H ₅ - ^■ IC-C0C ₂ H ₅ 1.4757

0

II

672 ^"C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -C(CH ₂ ) ₁₆ CH ₃ Slush

r

0

II

673 ^'G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CC 2H"5 1.4778

0

674 ^■ C ₇ H ₁₅ - ^G 7 ^H 15 ~ ^G 2 ^H 5 -CC _χ5 H ₃₁ Slush

0 ti

677

~ ^G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 1.4725

~ ^GC 11 ^H 23

0

678 •C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ S- NO, Slush

0

II

679 ^• C ₇ H ₁₅ ^"G 7 ^H 15 ~ ^G 2 ^H 5 -CCC1, 1.4960

680 ^*G 7 ^H 15 ~ ^G 7 ^H 15 -C ₂ H ₅ -

0

II

681

^"G 7 ^H 15 ^*"C ₇ ^H 15 -C ₂ H ₅

~ ^CG 9 ^H 19 1.4727

0

682 ^• C ₇ H ₁₅ - ^C 7 ^H 15 ~ ^C 2 ^H 5 -CC ₁₀ H ₂₁ 1.4732

0

II

683

^*G 7 ^H 15 ^"G 7 ^H 15 ^"G 2 ^H 5 -CC ₅ H _U 1.4748

Compound n 30

D or No. R R, R, R, °C

0

I'

684 -C ₆ H ₁₅ -C ₇ H ₁₅ ^"G 2 ^H 5 -CC ₆ H ₁₃ 1.4724

0 ιι

685 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CC ₇ H ₁₅ 1.4730

0

686 -C ₇ H ₁₅ -C ₇ H ₁₅ —C^Hc -CC ₈ H ₁₇ 1.4730

687 -C 7H"15 - -CK - 7iRn"1,5 -C ₂ H ₅

1.4932

^G 7 ^H 15

0

689 -C ₇ H ₁₅ - ^C 7 ^H 15 -C ₂ H ₅ -CSC(CH ₃ ) ₃ 1.4872

0 0

690 -C ₇ H ₁₅ ~ ^G 7 ^H 15 ^"G 2 ^H 5 -CCH ₂ CH ₂ COCH ₃ 1.4776

II"

691 ~ ^tc 8 ^H 17 -CgH ₁₇ ~ ^C 2 ^H 5 —CCOC^Hc 1.4809

ul'

692 -C ₈ H ₁₇ ^"G 5 ^H 11 -C ₂ H ₅ -CCOC ₂ H ₅ 1.4765

693 771

~ ^C 6 ^H 13 ^"G 6 ^H 13 -C ₂ H ₅ -CCOCΛHC 1.4

il II

694 •secCH- _ -C ₂ H ₅ -CCOC ₂ H ₅ / 13 - ^G 7 ^H 15 1.4757

Compound 30 n No. R Rn R, R- D or

0 ^G ιi I

697 ^tG 8 ^H 17 ~ ^G 7 ^H 15 -C ₂ H ₅ -CCOC ₂ H ₅ 1.4817

0 n il

698 ^tG 8 ^H 17 ^"G 4 ^H 9 -C ₂ H ₅ -CCOC ₂ H ₅ 1.4835

0

699 ? ^tG 8 ^H 17 ^"G 6 ^H 13 -C ₂ H ₅ -CCι0C ₂ H ₅ 1.4821

I

700

II '

701 ^• tC H, -secC ₇ H-, c -C ₂ H ₅ -CCOC ₂ H ₅ 1.4789

O 0

II "

704 -tC ₈ H ₁₇ -C ₈ H ₁₇ ^"G 1 ^H 3 -CCOC ₂ H ₅ 1.4809

705 ^■ secC ₇ H ₁₅ ~ ^C 7 ^H 15 "" ^G 3 ^H 7 -CCOC ₂ H ₅ 1.4748

706 -2-ethyl- -2-ethyl- -C ₂ H ₅ ^• CCOC ₂ H ₅ 1.4782 hexyl hexyl

I

0 0 t

1.4822

708 ^■ secC ₇ H- _| c ~ ^G 7 ^H 15 -C ₃ H ₇

^G 7 ^H 15

30

Compound No. R ^1 R, R, °C

0

«

710 1.4837

~ ^tc 8 ^H 17 -2-ethyl -C ₂ H ₅ -CCOC ₂ H ₅ hexyl

0 n I

711 -tC ₈ H ₁₇ -2-ethyl -C ₃ H _? -CCOC ₂ H ₅ 1.4818 hexyl

?I

712 -secC ₇ H ₁₅ -C ₇ H ₁₅ -C ₄ H ₉ •CCOC ₂ H ₅ 1.4748

713 -secC ₇ H ₁₅ -C ₆ H ₁₅ -C ₄ H ₉

^C 7 ^H 15

714 ^■ tC ₈ H ₁₇ -C ₃ H ₇ - fCCtOC ₂ H ₅ 1.4808

^"C 8 ^H 17

716 -C ₂ H ₅ -C ₂ H ₅ 1.4883

~ ^C 2 ^H 5

717 -2-ethyl- ₅ hexyl ^G 6 ^H 13 ^■ C ₂ H 1.4788

718 ^■ secCH-,c •C ₈ H ₁₇ ^•G 2 ^H 5

^G 8 ^H 17

720 -secC ₇ H ₁₅ -2-ethyl- -C ₂ H ₅ 1.4776 hexyl

721 -secC ₇ H ₁₅ -2-ethyl- -C ₃ H _? -CCOC ₂ H ₅ 1.4785 hexyl

722 -2-ethyl- 3 —CH/SCH 1.4983 hexyl ^G 6 ^H 1

723 Cl - t 1.5295 t

724 ~ ^G 7 ^U 15 ~ ^G 7 ^H 15 ^"C 2 ^H 5 -CCOC ₃ H ₇ 1.4766

725 ^"C 7 ^H 15 ~ ^C 7 ^H 15 •C ₂ H ₅ 1.4738

Compound n _D 30 or No. . R R^ R ₁ - R, °C

728 -C ₇ H ₁₅ ^"G 7 ^H 15 -C ₂ H ₅ Slurry

729 -secC ₇ H ₁₅ - ^C 8 ^H 1 -C _χ H ₃ 1.4752

730 Q- ^_C 7 ^H 15 -C ₂ H ₅ 1.5255

Compound n„ 30 or No. R Rn R, R ₃ D

°C

735 — Cqll- _| ι S (CHΛ n — CnHi -t -C ₂ H ₅ 1.4898

736 -(CH ₂ ) ₃ OCH ₃ nil

^"G 7 ^H 15 -C ₅ H ₁₁ ^■ CCOC ₂ H ₅ 1.4772

737 ^• secCH-i c -2-ethyl- hexyl ^iC 4 ^H 9

ii II

739 -CH ₃ 0(CH ₂ ) ₂ O(CH ₂ ) ₃ -C ₆ H ₁₅ ^"C 2 ^H 5 -CCOCΛHC 1.4777

H(CH ₃ ) ₂ 1.4723

Compound 30 No.- R " or

°c

li U

742 -secC ₇ H ₁₅ -2-ethyl- —IC H-ϊ -CCOC ₂ H ₅ 1.4764 hexyl

II 1

743 -secC ₇ H ₁₅ -2-e hyl- -CCOC ₂ H ₅ 1.4721 hexyl ^"G 7 ^H 15

0 ^G till

744 -CH ₃ 0(CH ₂ ) ₂ 0(CH ₂ ] ^f 3 ~ ^G 7 ^H 15 ^**G 5 ^H 11 ""CCOCΛΠC 1.4757

745

746 C ₂ H ₅ 1.4943

747 -secCH..c -C ₉ H ₁₉ -C ₂ H ₅ -CCOC ₂ H ₅ 1.4750

CH,

/ nil 749 -C ₂ H ₅ -Si-(CH ₂ ) ₄ 740

^"C 7 ^H 15 -C ₂ H ₅ -CCOC ₃ H ₇ -i 1.4

^N CH ₃

0 l>

751 ^"G 7 ^H 15 ^"G 7 ^H 15 -C ₂ H ₅ -CSCH, 1.4948

0

II

752 2

^•G 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CSC ₂ H ₅ 1.492

0

II

753 ^■ C ₇ H ₁₅ 1.4916

^"*G 7 ^H 15 -C ₂ H ₅ — CSC H-T _T

0 II

756 -C ₇ H ₁₅

- ^G 7 ^H 15 -C ₂ H ₅ -CSC^Hg-sec 1.4892

0

757 -C ₇ H ₁₅ ^"G 7 ^H 15 ~ ^G 2 ^H 5 -CSC ₄ H ₉ -i 1.4879

0

II

758 -C ₇ H ₁₅ ~ ^G 7 ^H 15 -C ₂ H ₅ -CSC ₈ H ₁₇ 1.4860

0

759 ^"G 7 ^H 15 5287

~ ^G 7 ^H 15 ^• C ₂ H ₅ -cs-<2> 1.

O

1.5250

ci 1.5366

n, 30

No. R D or

^R l R ₂ R ₃

762 -2-ethyl- -2-e hyl- -CH ₂ CH-CH ₂ -CCOC ₃ H ₇ -i 1.4800 hexyl hexyl

763 -2-ethyl- -2-e hyl- -C ₃ H ₇ -CCOC ₃ H ₇ -i 1.4749 hexyl hexyl o

764 -secC ₇ H ₁₅ -C ₈ H ₁₇ - _™2 -< -CCtOC ₂ H ₅ 1.5052

ull

765 ⁰¹ -Q- -secCH-,c -C ₂ H ₅ -CCOC ₂ H ₅ 1.5298

CH ₃

766 -C ₇ H ₁₅ -(CH ₂ ) ₃ N(C ₂ H ₅ ) ₂ -C ₂ H ₅ -CCOC ₃ H ₇ -l 1.4786

767 * ^■ *SβCij<γH.-| j* -CH ₂ - -C ₂ H ₅ - fCCtOC ₂ H ₅ 1.4909

768 -secC ₇ H ₁₅ 1.5114

^"C 8 ^H 17 -CHj -Cl

0 l°'

770 o ^~ CH ₂ - ^~ ™2- -C ₂ H ₅ CCOC ₃ H ₇ -i 1.5526

771 ₃ H ₇ -i 1.4882

H R

773 -aecC ₇ H _ι5 -C ₆ H ₁₃ -C ₂ H ₅ -CC0C ₃ H ₇ -i 1.4730

Compound No. R R, R, R, 30

"D ^or

0

774 •secC ₇ H ₁₅ -C _a H ₁₇ -C ₂ H ₅ -CNHC 8H"17 1.4756

0

II

775 •secC ₇ H ₁₅ -C ₈ H ₁₇ ^"C 2 ^H 5 -CNH-sec-C ₇ H ₁₅ 1.4766

776 ^■ SeC >-,ii- _| c — Qii- _| - _j -C ₂ H ₅ 1.5215

777 -secC ₇ H ₁₅ ~ ^C 8 ^H 17 -C ₂ H ₅

0 CH II / ³

778 -secC ₇ H ₁₅ ~ ^C 8 ^H 17 5219

^"G 2 ^H 5 -CNH 1. $-*>

CH,

-223-

LEPIDOPTERICIDAL EVALUATION

Lepidoptericidai activity of the above compounds were evaluated for efficacy on various lepidopterous species as follows:

I. Salt-Marsh Caterpillar [Estig ene acrea (Drury)]

A test solution is prepared by dissolv¬ ing the test compound in a 50-50 acetone-water solution. A section of a curly dock (Rumex crispus) leaf, approximately 2.5 cm wide and 4 cm long, is immersed in the test solution for 2-3 seconds, then placed on a wire screen to dry. The dried leaf is placed in a petri dish containing a moistened piece of filter paper, and infested with 5 second-instar salt-marsh caterpillar larvae. Mortality of the larvae is. recorded 48 hours later. If surviving larvae ^' re still present, a piece of synthetic media is added to the dish and the larvae are observed for an additional 5 days in order to detect delayed effects of the test compound. The primary screening level for this test is 0.05 percent by weight of the test compound in the solution.

II. Cabbage Looper [Trichoplusia ni (HUbner)]

The procedure for cabbage looper larvae is the same as that used for salt-marsh caterpillar larvae, except that a cotyledon of hyzini squash (Calabacita abobrinha) 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 0.05 percent by weight of the test compound in the solution.

III. Tobacco Budworm [Heliothis virescens (F.)3

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 (L tuca 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 lepidop¬ tericidai tests performed on the compounds of Table I. These test results are expressed as DH _Q 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 D _5Q for this group.

d EAl

OMPI

-225-

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" x 9" x 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 f-ats in a Ducon-Savko Model 3400 linear spray table at ι- ^~ ?tes 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 ^β 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 phyto¬ toxicity 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 lepidoptericidai activity can be conducted.

OMPI

Table II

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 111 1 2 111 1 2

1 .008 .01 >.05 0 0 2 0 0 2

- 2 .008 .003 .04. 0 0 1 0 1 2

3 .0024 .006 .03 0 0 3 0 1 1

4 .016 .0016 >.08 0 0 0 0 0 0

5 .003 .009 .15 1 4 4 1 4 4

6 .001 ^' .005 .05 . 0 0 2 0 0 2

7 .002 .0008 .02 0 1 4 0 1 4

8 .0009 .0009 ¹ .02 0 1 4 0 0 3

9. .0007 .002 .01 1 ^■ 3 5 0 2 5

10 .005 .0007 ^' .02 1 3 5 1 3 5

11 .008 .002 > .05 0 2 5 0 2. 5

12 .001 .002 > .05 0 1 5 0 2 5

13 .003 .003 > .05 1 2 5 1 2 5

14 .003 .005 > .05 1 3 5 0 2 4

15 .008 .008 >.05 1 2 5 0 1 3

16 .008 .008 .05 1 3 4 0 2 4

17 .001 .002 >.05 1 2 4 0 1 4

18 .05 .003 >.05 1 2 4 0 1 3

19 .003 .005 ^.05 0 2 5 0 2 5

20 .008 .002 >.05 1 2 4 0 1 3

21 .01 .003 > .05 0 1 2 0 1 2

22 .005 .0008 !^>.05 0 0 1 0 0 1

Phytotoxicity Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

.003 .0005 >.05 0 ^' 1 3 0 2 4

>.05 .01 >.05 0 1 3 ^' 0 1 2

.03 .005 >.05 0 2 4 0 2 3

>.05 .01 >.05 1 2 3 0 1 2

.005 .001 >.05 0 1 3 0 1 3

>.05 .003 .05 .- 0 1 3 0 1 2

.002 .002 >.05 0 0 0 0 0 1

.005 .002 .05 0 1 2 0 ^" 0 1

.005 .003 .05 0 1 2 0 1 3

.001 .002 .01 0 1 3 0 1 3

.008 .01 >.05 0 0 1 0 0 1

.005 .002 >.05 1 1 2 1 2 3

.01 .0005i>.05 0 1 2 1 2 3

.005 .002 >.05 0 1 2 0 1 3

.002 .002 .05 0 0 1 0 0 2

.003 .005 >.05 0 1 3 1 2 4

>.05 .1 > .05 0 0 2 0 1 3

.001 .001 .01 1 3 5 1 4 5

.003 .03 >.05 0 0 1 0 1 2

.001 .002 .05 0 2 3 1 2 5

.002 .002 >.05 0 2 5 1 3 5

>.05 .03 > .05 0 1 3 0 .2 4

- fRE

Compound LepidoptεriiΞidal Phytotoxicity No. Activity Cotton Squash

SMC CL '.raw 1/2 1/2

45 .01 .0005 .05 1 2 5 1 3 5

^• 46 .01 .002 .05 0 0 1 0 1 2

47 .001 .001 .03 0 1 3 0 2 4

48 .005 .001 .03 1 2 4 1 3 5

49 .0003 .0002 .05 1 2 5 1 3 5

50 .0003 .0003 .05 1 3 5 1 3 5

51 .001 .001 .05 0 2 5 0 2 5

52 .005 .003 0 1 2 0 0 2

53 .008 .005 0 0 1 0 0 1

54 .008 .005 0 0 0 0 0 2

55 .002 .002 0 1 2 0 1 2

56 .001 .0003 .02 1 2 3 1 3 4

57 .001 .0003 .02 0 2 4 1 2 5

58 .002 .0005 .05 0 2 3 0 3 5

59 .002 .0005 .05 0 1 3 0 1 3

60 .003 .002 > .05 0 0 0 ^* 0 0 0

61 .008 .005 .05 0 2 5 0 3 5

62 .0008 .001 .05 0 1 2 0 1 2

63 .001 .005 > .05 ^■ 0 0 1 0 0 2

64 .005 .008 .05 0 0 1 0 0 1

65 .0002 .0005 .02 1 2 5 1 3 5

66 .002 .03 .05 0 1 3 0 2 3

-230-

Compound Lepidoptericidai Phytotoxicity No . Activity Cotton Squash

SMC CL TB 1/2 1/2

67 .001 .002 .05 0 0 0 0 0 0 68 .0008 .005 .05 0 1 3 0 2 5 69 .0003 .002 >.05 0 1 3 0 1 5 70 .001 .002 >.05 0 1 3 0 1 4 71 .001 .0005 .05 0 1 4 0 1 4 72 .0008 .002 .05 ^■ 0 0 1 0 1 2 73 .002 .003 .06 0 0 1 0 0 1 74 .002 .002 .03 0 0 0 0 1 0 75 .003 .03 >.05 0 0 0 0 0 0 76 .003 .03 >.05 0 0 1 0 0 1 77 .01 .002 >.05 0 0 1 0 0 1 ^' 78 .002 .0005 .05 0 1 2 0 1 3 79 .005 .002 >.05 0 0 0 0 0 0 80 .002 .0005 .01 0 0 1 0 0 1 81 .003 .002 .05 0 0 0 0 0 1 82 .008 .002 >.05 0 1 3 0 1 4 83 .005 .003 >.05 0 0 1 0 0 1 84 .001 .0003 > .05 0 1 4 0 1 5 85 .005 .0003 .03 0 0 3 0 0 2 86 .002 .0008>.05 0 0 0 0 0 0 87 .002 .002 >.05 0 0 3 0 1 4 88 .003 .0002 > .05 0 0 3 0 0 4

OMPI

Compound Lepidoptericsidal Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

89 .001 .002 .05 0 0 0 0 0 0

^• 90 .001 .0002 .04 0 0 1 0 0 1

91 .0003 .0002 , .01 0 0 0 0 0 1

92 .005 .03 >. .05 0 0 0 0 0 0

93 .001 .001 > .05 0 0 2 0 1 3

94 .005 .002 > .05 - 0 0 1 0 0 1

95 .002 .0008> .05 0 0 0 0 0 1

96 .001 .0003 > .05 0 2 4 1 3 5

97 .0008 .0008 > .05 0 0 0 0 0 0

98 .001 .001 .05 0 1 3 0 1 3

99 .002 .0005 > .05 0 0 1 0 0 2

100 .003 .0005 .05 0 1 3 0 1 4

101 .001 .002 .05 1 2 4 1 3 5

102 .0003 .002 .06 0 0 0 0 0 1

103 <.05 .002 .03 1 2 4 1 2 5

104 .003 .002 .05 0 0 0 0 0 0

105 .005 .002 .05 0 0 0 0 0 0

106 .005 .0005 .05 0 1 4 0 2 4

107 .003 .0008 .05 0 0 1 0 0 2

108 .002 .001 > .05 0 1 2 0 1 3

109 .003 .002 .05 0 2 4 0 3 5

110 .01 .0005> .05 0 0 2 0 0 2

Compound Lepidoptericidai Phjrtoto:xicit-i 7

No. Activity Cotlton Sqtlash

SMC CL TBW 1/2 1 2 1/2 1 2

Ill .008 .05 >.05 0 0 0 0 0 0

^' 112. .001. .0003 .05 0 0 2 0 1 3

113 .005 .003 .05 0 0 0 0 0 0

114 .002 .0005 .05 0 0 2 0 1 3

115 .003 .008 >.05 0 0 0 0 0 0

116 .002 .003 <.05 ^• 0 0 0 0 0 0

. 117 .002 .002 >.05 0 0 0 0 0 1

118 .001 .0005 <.05 p 0 1 1 2 3

119 .05 .002 >.05 0 0 0 0 0 1

120 .002 .001 .05 0 0 0 0 0 0

121 .0005 .0005 .03 0 0 1 0 o. 2

122 .0001 .0005 .03 0 1 3 1 3 5

123 .0003 .001 .05 ^' 1 3 4 1 4 5

124 .05 .002 .05 0 1 2 0 1 3

125 .0008 .001 <.05 0 0 1 0 0 1

126 .0005 .0005 .03 0 1 3 1 2 4

127 .0008 .0.05 >.05 0 1 2 1 2 5

128 .001 .001 <.05 0 0 0 0 0 0

129 .005 .0005 .05 0 0 1 0 1 2

130 .002 .002 <.05 0 0 0 0 0 3

131 .008 .002 .05 0 0 0 0 0 0

132 .003 .002 <.05 0 0 1 0 . 1 3

Co pouπid Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1 2

133 .001 .005 05 0 0 1 0 0 2

- 134 .003 .001 >.l 0 0 0 0 0 1

135 .0008 .0005 <.05 0 0 2 0 1 3

136 .0002 .003 .05 0 0 0 0 0 1

137 .001 .03 >.ι 0 0 0 0 0 0

138 .005 .01 >.05 ^■ 0 1 2 0 1 2

139 .003 .002 <.05 0 0 0 0 0 1

140 .002 .001 <.05 0 0 1 0 0 0

141 .0005 .0005 .05 0 0 2 0 0 1

142 .01 .002 .05 0 0 0 0 0 0

143 >.05 .03 .05 0 0 0 0 0 0

144 .001 .002 <.05 ^• 0 0 0 0 0 0

145 .0003 .0005 <.05 0 0 1 0 0 2

146 >.05 .005 .05 - 0 0 0 0 0 0

147 .005 .002 <.05 0 0 2 0 0 2

148 .005 .0005 <.05 0 0 1 0 0 1

149 .005 .002 .05 0 0 0 0 0 0

150 .0001 .0003 <.05 0 1 2 0 1 3

151 >.05 .008 <.05 0 0 0 0 0 0

152 .002 .0003 .05 0 1 3 0 2 3

153 .002 .001 .08 0 0 0 0 0 0

154 .0003< _, .001 .02 0 0 1 0 0 1

/ TCT A

OMPI

WIPO

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1

155 >.05 >.05 >.05 0 0 0 0 0

^" 156 .03 .03 >.05 . 0 0 0 0 0

157 >.05 >.05 .04 0 0 0 0 0

158 >.05 .05 .05 0 0 0 0 0

159 .05 .008 >.05 0 0 0 0 0

160 >.05 .05 >.05 ^• 0 0 1 0 0

161 >.05 .03 .05 0 0 0 0 0

162 >.05 . .1 >.05 0 0 0 0 0

163 ; >.05 .01 .04 0 0 0 0 0

164 .008 >.05 .05 0 0 1 0 0

165 >.05 >.05 .05 0 0 1 0 0

166 >.05 >.05 >.05 0 0 1 0 0

167 >.05 >.05 .05 0 1 2 0 0

168 >.05 .01 ^* .05 0 0 0 0 0

169 .03 .005 >.05 0 0 0 0 0

170, >.05 >.05 >.05 0 0 0 0 0

171 >.05 .4 >.05 0 0 0 0 0

172 .003 <.001 >.05 0 0 0 0 0

173 .01 .003 >.05 0 0 0 0 0

174 >.05 .03 >.05 0 0 1 0 0

175 - >.05 >.05 >.05 0 0 1 0 1

176 .05 >.05 >.05 0 0 1 0 . 0

Compound Lepidoptericidai Ph] rtotoxicity No. Activity Cotton Squa .sh

SMC CL TB 1/2 1 2 172 1 2

177 >.05 .2 >.05 0 0 1 0 0 1

^" 178 > .05 .05 >.05 0 0 1 0 0 1

179 > .05 .01 >.05 0 o ^• 1 0 0 1

180 .005 > .05 >.05 ^■ 0 1 3 0 1 2

181 .05 .01 >.05 0 0 0 0 0 1

182 .03 .008 >.05 - 1 2 4 1 2 4

183 > .05 > .05 .05 0 0 0 0 0 0

184 .01 .003 >.05 0 0 0 0 0 0

185 > .05 .5 ^■ .05 0 0 0 0 0 0

186 > .05 .05 >.05 0 0 0 0 0 0

187 >.05 .01 >.05 0 0 0 0 0 0

188 >.05 .5 >.05 0 0 .1 0 0 0

^' 189 .003 .01 >.05 0 0 1 0 0 1

190 >.05 .008 >.05 0 0 0 0 0 0

191 .01 .15 >.05 0 2 3 0 2 4

192 >.05 .01 >.05 0 1 2 0 1 3

193 .4 0 0 1 0 0 2

194 .2 0 0 2 0 0 2

195 .001 .002 >.05 0 1 2 0 1 3

196 >.05 .01 >.05 0 1 2 0 0 2

197 .2 0 0 1 0 1 2

198 .5 0 1 2 0 • 0 1

/

/ ^{^} δU £

-236-

Compounc 3 Le pidoptericidal Pfrj rtoto: xicit-' ψ

No. Activity Coti ton Sq; 2ash

SMC CL TB 1/2 1 2 1/2 1 _^ 2

199 >.05 .2 >.05 1 2 4 1 3 5

200 .01 .0025 >.05 1 3 5 2 3 5

201 .05 >.05 >.05 0 0 0 0 0 0

202 .05 >.05 >.05 0 0 0 0 0 0

.203 >.05 >.05 .03 0 0 0 0 0 0

204 >.05 .1 >.05 ^'" 0 0 0 0 0 o

205 >.05 -.1 >.05 0 0 0 0 0 0

206 .03 .03 >.05 ^• 0 0 0 0 0 0

207 .03 .03 >.05 ό 0 0 0 0 0

208 .03 .008 .05 0 0 0 0 0 0

209 .01 .01 >.05 0 0 0 0 0 0

210 >.05 >.05 >.05 0 0 0 0 0 0

211 .05 >.05 >.05 0 0 0 0 0 0

212 .01 .002 .05 0 0 1 0 0 1

213 >.5 >.05 > .5 0 0 0 0 0 1

214 >.05 0 0 0 0 0 1

215 >.05 0 0 0 • 0 0 0

216 .008 .005 >.05 0 0 2 0 0 1

217 .05 >.05 >.05 0 0 1 0 1 2

218 .05 .003 >.05 0 1 2 0 1 2

219 .005 .008 >.05 0 0 0 0 0 2

220 .03 .004 .05 0 0 1 0 : 0 1

Compoundi Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1 2

221 .01 .004 .05 0 0 1 0 1 2

222 >.05 .3 >.05 0 0 0 0 0 0

223 .003 .008 >.05 0 0 0 0 0 0

224 .03 .002 >.05 0 0 0 0 0 1

225 .01 .03 > .05 0 0 1 0 0 ^" 2

226 .005 .005 >.05 , 0 0 1 0 0 1

227 .03 .0008 >.05 0 1 2 0 1 3

228 .003 .002 .05 0 1 2 0 1 2

229 .01 .009 .l 0 1 3 0 2 4

230 .003 .001 >.l 1 3 5 1 3 5

231 .001 .0005 >.l 2 5 5 1 5 5

232 .001 .0005 >.l 0 2 5 0 2 5

233 .003 .0008 >.l 1 4 5 0 3 5

234 .002 .002 .1 0 2 5 0 2 5

235 .003 .0008 .1 1 4 5 0 3 5

236 .003 .0005 >.l 1 3 5 1 3- 5

237 .002 .0005 .1 1 5 5 1 5 5

238 .002 .003 >.05 0 0 0 0 0 1

239 .03 .03 >.05 0 0 2 0 0 2

240 .03 .03 > .05 0 1 2 0 1 3

241 >.05 .005 >.05 0 0 3 .0 1 5

242 .01 .005 >.05 0 0 2 0 1 5

-SJ E ^

Compound Lepidoptericidai Phytotoxicity No, Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1

243 .03 .005 > .05 0 0 3 0 1

^" 244 .03 .01 >.05 0 1 3 0 1

245 .008 .03 .05 0 1 3 0 1

246 .05 .005 >.05 0 0 2 0 1

247 .01 .002 >.05 0 0 1 0 0

248 .01 .01 >.05 ^• 0 0 0 0 0

249 >.05 > .05 .05 0 0 0 0 0

250 >.05 ...2 >.05 0 0 0 0 0

251 .01 .005 >.05- 0 0 2 o - 1

252 >.05 ^• .03 .05 0 0 1 0 0

253 >.05 .03 > .05 0 0 0 0 0

254 >.05 .05 >.05 0 0 0 0 0

255 >.05 >.05 .05 0 0 0 ^" 0 0

256 >.05 .15 >.05 0 0 0 0 0

257 >.05 .1 ^' >.ι 0 0 0 0 0

258 .05 >.05 .ι 0 0 0 0 0

259 >.05 >.05 .01 0 0 0 0 0

260 .008 .03 >.05 0 0 0 0 0

261 >.05 .05 >.05 0 0 0 0 ^' 0

262 .05 >.05 >.05 0 0 0 0 0

263 .005 .005 >.05 0 1 1 0 1

264 .005 .005 >.05 0 0 1 0 • 0

OMPI

-239-

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1 2

265 .03 .003 >.05 0 0 2 0 1 3

.266 >.05 .4 >.05 0 0 1 0 1 2

267 .005 .003 > .05 0 0 0 0 1 2

268 .03 .002 >.05 0 0 2 0 0 2

269 .03 >.05 >.05 0 0 1 0 1 2

270 .003 .002 .03 .- 0 1 3 0 1 4

271 .003 .002 .05 0 2 5 1 2 5

272 .002 .002 .05 1 2 4 i ^' 3 5

273 .005 .002 .05 1 2 4 1 3 5

274 .002 .001 .05 0 1 2 0 1 3

275 .001 .0005 .05 0 0 2 0 1 3

276 .003 .0008 >.05 0 0 2. 0 1 3

277 .001 .002 >.05 0. 1 2 0 ^' 1 2

278 .003 .001 .05 0 1 4 0 1 5

279 .003 '.001 >.05 0 1 2 0 1 3

280 .003 .0005 .05 0 1 4 0 1 5

281 .001 .001 .06 1 2 4 0 2 5

282 .005 .0005 .05 1 2 4 0 1 5

283 .01 .002 .05 0 1 2 0 1 3

284 .001 .0008 .05 1 4 5 1 4 5

285 .001 .0002 >.05 0 ^' 1 3 0 3 5

286 .001 .0002 .05 0 0 2 0 0 3

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC 1 CL TBW 1/2 1 2 1/2 1

287 .005 .0005 .02 0 0 3 0 0

- 288 .002 .0005 .02 0 0 1 0 0

289 .002 .001 >.05 0 0 0 0 0

290 .002 .0008 .03 0 0 0 0 0

291 .001 .002 .05 0 0 0 0 0

292 .003 .005 .01 . 0 0 0 0 0

293 .001 .0005 .01 0 0 0 0 0

294 .001 .0002 >.05 0 0 0 0 0

295 .002 .03. >.05 0 0 0 0 0

296 .0005 .001 .05 0 0 0 0 0

297 .002 .002 .05 0 0 0 0 0

298 .003 .005 >.05 0 0 2 0 1

299 .008 .003 >.05 0 1 3 0 2

300 .005 .003 .05 0 0 0 0 0

301 .003 .001- .05 0 0 0 0 0

302 .03 .03 >.05 0 0 1 0 1

303 >.05 .03 >.05 0 0 0 0 0

304 >.05 .01 >.05 0 0 0 0 0

305 >.05 > .05 .04 0 0 0 0 0

306 >.05 >.05 .05 0 0 1 0 1

307 >.05 >.05 >05 0 0 1 0 2

308 >.05 >.05 >.05 0 0 1 o . 0

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1/2

309 >.05 >.05 >.05 0 0 0 0 0 1

^• 310 >.05 >.05 .05 0 0 0 0 0 0

311 .05 >.05 > .05 0 0 0 0 0 0

312 .04 .05 >.05 0 0 0 0 0 0

313 .002 .003 .04 0 2 4 1 3 5

314 .002 .005 >.05 2 3 5 3 4 5

315 <.008 <.008 .05 1 3 5 2 3 5

316 .04 .04 >.05 0 0 0 0 0 ^" 0

317 -.05 >.05 0 0 0 0 0 1

318 >.05 > .05 0 0 0 0 0 0

319 .002 .002 .04 1 2 3 1 2 4

320 .005 .008 > .05 0 0 1 0 0 2

321 .002 .002 .02 1 2 4 2 3 5

322 .002 .003 .03 1 3 5 1 3 5

323 .005 .01 .05 0 1 2 0 1 2

324 >.05 .5 > .05 0 0 0 0 0 0

325 .03 .003 >.05 0 0 1 0 0 0

326 .002 .001 .03 1 2 5 2 3 5

327 .003 .002 .05 1 2 5 2 3 5

328 .002 .003 .04 1 2 5 2 3 5

329 ..002 .003 >.05 0 1 3 1 2 3

330 .002 .005 >.05 0 0 0 0 0 0

^• Tϋ EX^

-242-

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1/2

331 .001 .003 > .05 0 0 0 0 0 0

^■ 332 .002 .005 >.05 0 0 0 0 0 0

333 .05 >.05 >.05 0 0 0 0 0 0

334 .03 .008 >.05 0 0 0 0 0 0

335 > .05 .1 >.05 0 0 0 2 4 5

336 > .05 .1 >.05 0 0 0 0 0 0

337 .03 >.05 > .05 0 0 0 0 0 0

338 .005 .002 .05 1 3 5 1 2 5

339 .005 .002 >.05 1 3 4 1 2 3

340 .03 .005 .03 0 1 3 1 2 3

341 .01 .008 >.05 0 2 3 1 2 3

342 .01 .009 .05 0 0 1 0 1 2

343 .002 .005 >.05 0 2 3 1 2 4

344 > .05 .1 >.05 0 0 0 0 0 0

345 .002 .003 .03 0 1 3 1 2 3

346 .03 .008 > .05 0 0 0 0 0 1

347 .03 .009 >.05 0 0 0 0 0 0

348 .005 .002 .05 0 1 4 0 1 3

349 > .05 .05 >.05 0 2 4 0 2 3

350 .005 .005 .03 0 1 4 1 2 3

351 .03 .005 > .05 0 1 2 ϊ 2 3

352 .005 .003 >.05 0 0 2 1 1 2

Compound Lepidoptericidai Phytotc jxicity

No. Activity Cot1 :on Squash

SMC : CL TBW 1/2 1 2 1/2 1 2

353 .03 .002 .05 0 0 0 0 0 0

. 354 .002 .002 .01 0 0 0 0 0 0

355 .002 .001 .05 0 3 4 1 2 5

356 .005 .005 >.05 0 1 2 0 2 4

357 .03 .005 .05 0 0 0 0 0 0

358 .05 >.05 .05 0 0 0 0 0 0

359 .002 .005 .05 0 2 3 1 2 2

360 - .005 .002 .05 0 1 3 1 2 3

361 .01 .003 >.05 0 . 0 0 0 0 0

362 .008 .008 >.05 0 0 0 0 0 0

363 .05 .002 .05 0 0 0 0 0 0

364 .005 .002 .05 0 0 1 0 0 1

365 .05 .2 >.05 0 0 0 0 0 0

366 -05 >.05 .05 0 0 0 0 0 0

367 .003 .005 >.05 0 1 2 0 1 2

368 >.05 .03 .05 0 0 0 0 0 0

369 .003 .003 .05 0 1 2 0 1 2

370 .005 .005 .05 0 0 2 0 0 2

371 .003 .008 .05 0 1 3 0 1 2

372 .002 .002 >.05 0 0 1 0 1 2

373 .002 .005 >.05 0 2 4 1 2 3

374 .001 .002 >.05 0 1 2 0 1 2

-244-

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC : CL TB 1/2 1 2 1/2 1 2

375 .002 .002 >.05 . 0 0 0 0 0 0

^• 376 .003 .005 .05

377 .002 .0005 .05 0 0 0 0 0 1

378 .003 .005 .05 0 0 0 0 0 1

379 .002 .003 .05 0 0 0 0 0 0

380 .002 .0003 .05 0 0 0 0 0 0

381 .002 .003 >.05 0 0 0 0 0 0

382 .002 .0005 .1 0 0 0 0 0 0

383 .001 .002 .05 0 1 2 1 ^■ 2 3

384 .002 .0008 .05 0 0 0 0 0 1

385 .002 .0005 .05 0 0 1 0 0 2

386 .016 .0016 >.08 0 0 0 0 0 0

387 .003 .009 .15 1 4 4 1 4 4

388 .0024 .006 .03 0 0 3 0 1 1

389 .004 .0008 >. 0 0 2 0 0 2

390 .05 .03 .05

391 >.05 >.05 >.05

392 .05 >.05 .05

393 ^' .01 .01 >. 0 0 0 0 0 0

394 .05 .03 ^• ! 0 0 0 0 0 0

395 .05 >.05 > ' ¹ 0 1 3 0 1 2

396 .01 .005 >- 0 0 0 0 0 0

Compound Lepidoptericidai Phytotoxicity No. Ac ivity Cotton Squash

SMC I CL TBW 1/2 1 2 1/2 1 2

397 .05 >.05 ^• ! 0 0 0 0 0 2

398 .05 " .003 >- ^l 0 1 3 0 2 3

399 .01 .01 .03 0 0 0 0 0 0

400 .05 .04 0 0 0 0 0 0

401 .002 .002 1 2 5 1 3 5

402 .05 >.05 0 0 0 0 0 0

403 .001 .002 0 2 4 1 2 5

404 .03 .008 0 0 0 0 0 0

405 .03 .01 0 0 _. 0 0 0 1

406 .03 .03 0 0 0 0 0 0

407 .03 .008 0 0 0 0 0 1

408 .03 .03 >.05 0 0 0 0 0 0

409 .003 .005 >.05 0 0 0 0 0 0

410 .0008 ^' .002 .05 0 0 0 0 0 1

411 .005 ^'" .002 .04 0 1 3 1 3 ■ 4

412 .003 .002 >.05 0 0 2 0 0 2

413 .003 .001 .04 0 0 0 0 0 0

414 .005 .003 .04 0 0 1 0 0 1

415 .002 .001 .04 0 1 3 0 1 2

416 .005 .002 .04 0 0 0 0 0 1

417 .003 .0025 >.05 0 0 0 0 0 0

418 .008 .003 >.05 0 0 0 0 0 0

g SREAj?

Compound Lepidoptericidai Phytotoxicity No, Ac ivity Cotton Squash

SMC I CL TBW 1/2 1 2 1/2 1 2

419 .002 _. .002 > .05 0 0 0 0 0 0

^' 420 .01 .003 >.05 0 0 0 0 0 0

421 .002 .005 .03 0 0 1 0 0 2

422 .005 .002 .05 0 0 1 0 0 2

423 .008 .003 <.01 0 0 0 0 0 2

424 .03 .001 .05 0 0 0 0 0 0

425 .01 .002 >.05 0 0 2 0 0 2

426 .01 .005 >.05 0 1 2 0 •1 2

427 .01 .002 >.05 0 0 0 0 0 0

428 .03 .005 >.05 0 0 0 0 0 0

429 .002 .001 >.05 0 0 0 0 0 0

430 .005 .002 >.05 0 0 0 0 0 1

431 .01 .002 >.05 0 0 0 0 0 2

432 .005 .005 >.05 0 0 2 0 0 2

433 .005 .005 >.05 0 0 0 0 0 0

434 .01 .03 >.05 0 0 0 0 0 0

435 .01 .002 >.05 0 0 0 0 0 0

436 .003 ^' .001 .05 0 0 0 0 0 1

437 .005 ^" .001 > .05 0 0 0 0 0 0

438 .003 .002 >.05 0 0 1 0 0 1

439 .003 .003 >.05 0 0 1 0 0 2

440 .003 .003 > .05 0 0 0 0 0 0

. / ^■ fc

OMPI

-247-

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

441 .005 .002 >.05 0 0 0 0 0 0

- 442 .003 .005 >.05 0 0 0 0 0 2

443 .003 .005. >.05 0 0 0 0 0 0

444 .008 .01 >.05 0 0 0 0 0 0

445 .001 .01 >.05 0 0 0 0 0 0

446 .003 .008 >.05 0 0 0 0 0 0

447 .008 .01 >.05 0 0 0 0 0 0

448 .005 .005 >.05 0 0 0 0 ^• 0 1

449 .008 .005 >.05 0 0 0 0 0 0

450 .005 .005 >.05 0 p 0 0 0 0

451 .005 .03 .05 0 0 0 0 0 0

452 .001 .001 .05 0 0 0 0 0 0

453 .002 .005 .05 0 0 0 0 0 0

454 .001 .003 >.05 0 0 0 0 0 0

455 .008 .002 .06 0 0 1 0 0 1

456 .002 .002 .05 0 0 0 0 0 0

457 .005 .002 .05 0 0 0 0 0 0

458 .005 .01 >.05 0 0 0 0 0 0

459 .008 .01 .05 0 0 0 0 ^• 0 0

460 .003 .002 >.05 0 0 0 0 0 0

461 .005 .002 >.05 0 0 0 0 0 0

462 .005 .002 >.05 0 0 0 0 0 0

- O:-:H ^'

-248"

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

463 .005 .005 .05 0 0 0 0 0 0 464 .002 .005 .05 0 0 0 0 0 0 465 .005 .002 >.05 0 0 0 0 0 0 466 .003 .002 .05 0 0 0 0 0 0 467 .003 .002 >.05 0 0 1 1 0 2 468 .002 .002 >.05 ^■ 0 0 0 0 0 0 469 .002 .002 >.05 0 0 0 0 0 0 470 .002 .003 .05 0 0 0 0 0 0 471 .002 .005 >.05 0 0 0 0 0 0 472 .003 .005 >.05 0 0 0 0 0 1 473 .002 .002 >.05 0 0 0 0 0 0 474 .002 .002 .05 0 0 0 0 0 1 475 .002 .005 >.05 0 0 0 0 0 1 ^' 476 .002 .002 .05 0 0 0 0 0 0 477 .005 .002 >.05 0 0 0 0 0 0 478 .003 .002 >.05 0 0 0 0 0 0 479 .005 .01 ^■ .05 0 0 0 0 0 0 480 .003 .002 >.05 0 0 0 0 0 0 481 .003 .002 .03 0 0 0 0 0 1 482 .008 .003 .05 0 0 0 0 0 1 483 .005 .002 >.05 0 0 0 0 0 0 484 .003 .002 >.05 0 0 0 0 0 0

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC : CL TB 1/2 1 2 1/2 1 2

485 .003 .002 >.05 0 0 0 0 0 0

^' 486 .005 .002 >.05 0 0 0 0 0 0

487 .001 .005 >.05 0 0 0 0 0 0

488 .003 .002 .05 0 .0 0 0 0 1

489 .01 .002 >.05 0 0 0 0 0 0

490 .002 .002 >.05 0 0 0 0 0 0

491 .005 .003 >.05 0 0 0 0 0 0

492 .003 .002 >.05 0 0 0 0 0 0

493 .005 .005 >.05 0 0 0 0 0 1

494 .01 .005 >.05 0 0 0 0 0 0

495 .01 .002 >.05 0 0 0 0 0 0

496 .003 .001 05 0 0 0 0 0 0

497 .001 .002 .01 0 0 0 0 0 0

498 .0008 .005 .03 0 0 0 0 0 0

^' 499 .002 .002 .01 0 0 0 0 0 0

500 .003 .002 .05 0 0 0 0 0 0

501 .002 .002 .03 0 0 0 0 0 0

502 .003 .002 >.05 0 0 0 0 0 0

503 .002 .001 >.05 0 0 0 0 0 0

504 .005 .002 >.05 0 0 0 0 0 0

505 .008 .001 >.05 0 0 0 0 0 0

506 .002 > .003 .01 0 0 0 0 0 0

P EXC

OMPI

Compound Lep•idoptericidal Phvtoto:sicity

No. Activity Cot1 :on Squiash

SMC 1 CL TB 1/2 1 2 1/2 1 2

507 .002 .005 >.05 0 0 0 ^• 0 0 0

508 .001 .002 .03 0 0 0 0 0 0

509 .001 .002 .05 0 0 0 0 0 0

510 .005 .001 >.05 0 0 0 0 0 0

511 .001 .005 >.05 0 0 0 0 0 0

512 .001 .005 .05 0 0 1 0 0 1

513 .002 .005 >.05 0 0 1 0 0 1

514 .005 .006 >.05 0 0 0 0 0 0

515 .002 .002 .05 0 0 0 0 0 0

516 .001 .005 >.05 0 0 0 0 0 0

517 .002 .002 >.05 0 0 1 0 0 1

518 .003 .005 >.05 0 0 0 0 0 1

519 .001 .005 >.05 0 o- 0 0 0 0

520 .001 .005 >.05 0 0 0 0 0 0

521 .008 .003 >.05 0 0 0 0 0 0

522 .005 .003 >.05 0 0 0 0 0 0

523 .005 .005 >.05 0 0 0 0 0 0

524 .002 .0002 >.05 0 0 0 0 0 0

525 .002 .001 >.05 0 0 0 0 0 0

526 .002 .0005 >.05 0 0 0 0 0 0

527 .002 .0003 >.05 0 0 0 0 0 0

528 .002 .0002 : .05 0 0 1 0 1 3

ompound Lepidoptericidai

SMC CL TBW 1/2 1 2 1/2 1 2

529 .002 .0002 >.05 0 0 0 0 0 0

^' 530 .002 .001 >.05 0 0 0 0 0 0

531 .002 .001 >.05 0 0 0 0 0 0

532 .001 .0002 .05 0 0 0 0 0 2

533 .002 .0001 <.05 0 0 0 0 0 0

534 .002 .002 .05 0 0 0 0 0 0

535 .002 .0002 >.05 0 . 0 0 0 0 0

536 .002 .0005 >.05 0 0 0 0 0 0

537 .001 .0005 .05 0 0 0 0 0 0

538 ^' .002 .002 .05 0 0 0 0 0 0

539 .001 .0005 .05 0 0 0 0 0 0

540 .002 .0001 .05 0 0 o ^• 0 0 0

541 .0002 .001 .05 0 0 0 0 0 0

542 .03 .002 .05 0 0 0 0 0 0

543 .0005 .0003 <.05 0 0 0 0 0 0

544 .002 .0001 .05 0 0 0 0 0 0

545 .03 .002 .05 0 0 0 0 0 0

546 .001 .0001 .05 0 0 0 0 0 0

547 ^' .0005 .0005 .05 0 0 1 0 0 3

548 .001 .0003 <.05 0 0 1 0 0 1

549 .002 .0002 .05 0 0 0 0 0 0

550 .002 .0002 .05 0 0 0 0 0 0

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Scuash

SMC CL TB 1/2- 1 2 1/2 1 2

551 .03 .001 .05 0 0 1 0 0 1

552 .0003 .0002 .05 0 0 0 0 0 1

553 .001 .0003 <.05 0 0 0 0 0 1

554 .001 .0003 .05 0 0 0 0 0 0

555 .002 .0008>.05 0 0 0 0 0 0

556 .0005 .0001 <.05 0 0 0 0 0 1

557 .0005 .0002 .05 0 0 0 0 0 2

558 .0002 .0003 <.05 0 0 0 0 0 ^" 0

559 .003 .002 .05 0 0 1 0 0 1

560 .003 .002 >.05 0 0 0 ^• 0 0 1

561 .001 .002 .03 0 1 3 0 1 5

562 .001 .001 .05 0 0 2 0 0 2

563 .001 .0003 .05 0 0 0 0 0 0

564 .003 .0005 >.05 0 0 2 0 1 3

565 .002 .0005 >.05 0 1 2 0 1 2

566 .0005 .0005 .05 0 0 2 0 1 3

567 .0003 .0005 .05 0 0 2 0 1 2

568 .0003 .0002 >.05 0 0 1 0 1 2

569 .0008 .0003 .02 0 0 0 0 0 1

570 .0003 .0003 .05 0 0 1 0 0 1

571 .0005 .0003 >.05 0 0 2 0 1 2

572 .0002 .0002 .05 0 0 2 0 1 3

^*

Compound Lepidoptericidai Phytotoxicitv No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

573 .001 .0005 >.05 0 0 1 0 1 2

574 .001 .0005 >.05 0 0 2 0 1 2

,575 .01 .0008 >.05 0 0 1 0 1 2

576 .0002 .0005 >.05 0 0 1 0 0 2

577 .0002 .0003 .05 0 0 1 0 0 2

578 .0005 .0005 >.05 0 0 1 0 0 2

579 .0005 .0005 >.05 0 0 0 0 1 2

580 .0005 .0008 >.05 0 0 0 0 0 1

581 .0002 .0005 .05 0 0 0 0 0 1

582 .0002 .0005 .005 0 0 1 0 0 2

583 .0003 .0003 >.05 0 0 1 0 0 2

584 .002 .001 .05 0 0 0 0 0 0

585 .003 .002 .05 0 0 0 0 0 0

586 .03 .005 .05 0 0 1 0 0 0

587 .01 .002 .05 0 0 0 0 0 0

588 >.05 .05 .05 0 0 0 0 0 0

589 >.05 .008 .05 0 0 0 0 0 0

590 .05 .002 >.05 0 1 3 0 1 2

591 .05 .01 .05 0 0 1 0 0 0

592 .01 .01 >.05 0 0 0 0 0 0

593 .03 .01 >.05 0 0 0 0 0 0

594 .005 .002 .05 0 0 0 0 0 0

Compound Lepidoptericidai Phytotoxicity No, Activity Cotton Squash

SMC CL TB 172 1 2 1/2 1 2

595 > .05 .005 .05 0 0 0 0 0 0

596 .002 .002 .04 0 0 0 0 0 0

597 .005 .005 .05 0 0 0 0 0 1

598 .005 .01 > .05 0 0 0 0 0 1

599 .001 .0002 .02 0 0 0 0 0 1

600 <.001 .0005 .04 0 0 0 0 0 0

601 .001 .0003 .005 0 0 1 0 0 1

602 .002 .003 >.05 • 0 1 2 0 1 2

603 .002 .0003 .08 0 0 0 0 0 1

604 .003 .003 .05- 0 0 1 0 0 ^• 1

605 .003 .05 >.05 0 0 0 0 0 0

606 >.05 .4 >.05 0 0 0 0 0 0

607 >.05 .05 >.05 0 0 0 0 0 0

608 >.05 .2 >.05 0 0 0 0 0 0

609 .003 .0003 .05 0 0 1 0 0 1

610 .002 .0005 >.05 0 0 2 0 0 1

611 .008 .0002 >.05 0 0 1 0 0 1

612 .002 .001 >.05 0 0 1 0 0 1

613 .003 .001 .05 0 0 1 0 0 1

614 .01 .003 >.05 0 0 1 0 0 1

615 .001 .002 .04 0 0 2 0 0 2

616 .004 <.001 >.05 0 0 1 0 0 2

-255-

Compound Lepidoptericidai Phytotoxicity Activity Cotton Squash

SMC CL TB 1/2 1/2

617 .003 .01 .05 0 0 1 0 0 2

- 618 .001 .005 .05 0 0 2 0 0 1

619 .002 .005 .05 0 0 1 0 0 2

620 .002 .002 >.05 0 0 1 0 0 1

621 .01 .003 .05 0 0 0 0 0 0

622 .03 .001 >.05 0 0 1 0 0 1

623 .002 .01 >.05 0 0 1 0 0 1

624 .001 .0008 .03 0 0 0 0 0 1

625 - .003 .001 .05 0 0 0 0 0 0

626 .003 .0005 .03 0 0 1 0 0 1

627 .005 .001 .01 0 0 1 0 0 1

628 .003 .001 >.05 0 0 0 b 0 0

629 .001 .0005 >.05 0 0 0 0 0 0

630 .003 <.001 .05 0 1 2 0 1 2

^" 631 >.05 .01 >.05 0 0 1 0 0 1

. 632 .005 .02 ^* .05 0 0 1 0 1 2

633 .01 .01 .1 0 0 1 0 0 0

634 .002 .003 .05 1 2 4 1 2 3

635 .008 .002 .05 0 0 1 0 0 1

636 >.05 .1 .05 0 0 0 0 0 0

637 .002 .003 >.05 0 1 3 0 1 4

638 .003 .003 >.05 0 1 3 0 2 4

-256-

Co pound Lepidoptericidai Phytotoxicity

No. Activity Cotton Squash

SMC CL TBW 1/2 1/2

639 > .05 .1 >.05 0 0 0 0 0 0

^• 640 .008 .05 >.05 0 1 2 0 1 3

641 > .05 .15 > .05 0 0 0 0 1 2

642 > .05 .2 >.05 0 0 0 0 0 0

643 .003 .03 >.05 0 0 1 1 2 3

644 .01 > .05 >.05 ^• 0 0 0 0 0 0

645 .01 > .05 >.05 0 0 0 0 0 0

646 .03 .05 >.05 0 _. 0 0 0 0 0

647 .03 > .05 >.05 0 0 0 0 0 0

648 .01 > .05 .05 0 0 0 0 0 0

649 .003 > .05 >.05 0 0 0 0 0 0

650 .003 .003 >.05 0 1 2 0 1 3

651 .05 .03 >.05 0 0 0 0 0 0

652 .05 .03 >.05 0 0 0 0 0 0

653 .002 .002 <.05 0 1 2 0 1 3

654 > .05 .4 >.05 0 0 0 0 0 0

655 > .05 .2 >.05 0 0 0 0 0 0

656 > .05 .1 >.05 0 0 0 0 0 0

657 .05 > .05 >.05 0 0 0 0 0 0

658 .03 > .05 >.05 0 0 0 0 0 0

659 > .05 .05 .03 0 0 0 0 0 0

660 > .05 .03 >.05 0 0 0 0 0 0

v -

-257-

Phytotoxicity

No. Activity Coti ton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

661 .03 .01 >.05 0 3 5 1 ^' 4 .5

^' 662 >.05 .05 >.05 0 0 0 0 0 0

663 .002 .005 .05 0 0 1 0 1 2

664 <.001 .002 >.05 0 0 0 0 0 0

665 <.001 .005 .05 0 0 0 0 0 0

666 <.001 .001 >.05 0 0 0 0 0 1

667 .03 >.05 >.05 0 0 0 0 0 0

668 .03 .1 >.05 0 0 0 0 0 0

669 .002 .002 .05 0 1 2 1 3 4

670 .03 .05 >.05 0 0 0 0 0 ^' 0

671 .001 <.001 .05 0 0 0 0 0 0

672 >.05 >.05 >.05 0 0 0 0 0 0

673 >.05 .5 >.05 0 0 0 0 0 0

674 >.05 >.05 >.05 0 0 0 0 0 0

675 .05 >.05 >.05 0 0 0 0 0 0

676 >.05 >.05 >.05 0 0 0 0 0 0

677 >.05 .2 >.05 0 0 0 0 0 0

678 >.05 .1 >.05 0 0 0 0 0 0

679 .003 .003 >.05 0 0 1 0 1 2

680 .002 .002 >.05 0 1 2 0 0 1

681 >.05 .1 >.05 0 0 0 0 0 0

682 >.05 >.05 >.05 0 0 0 0 0 0

-

-258-

Compound Lepidoptericidai Phytotoxicity

No. Activity ^* Cotton Squash

SMC CL TB 1/2 1 2 1/2 1

683 >.05 >.05 >.05 0 0 0 0 0

684 >.05 .1 >.05 0 0 0 0 0

685 >.05 .15 >.05 0 0 0 0 0

686 >.05 >.05 >.05 0 0 0 0 0

687 >.05 >.05 >.05 0 0 0 0 0

688 .03 .003 .05 0 0 1 0 0

689 .01 .03 >.05 _, 0 1 2 0 1

690 >.05 .1 >.05 0 0 0 0 1

691 .008 .002 >.05 0 0 0 0 0

692 .008 .008 .05 0 0 0 0 0

693 .03 .03 >.05 0 0 0 0 0

694 .0003 .002 .03 0 0 0 0 0

695 .002 .005 .03 0 0 0 0 0

696 .0005 .0008 >.05 0 0 0 0 0

697 >.05 .03 >.05 0 0 0 0 0 .

698 >.05 .03 >.05 0 0 0 0 0

699 >.05 .12 >.05 0 0 0 0 1

700 .008 .03 >.05 0 0 0 0 0

701 >.05 .4 >.05 0 0 0 0 0

702 >.05 .4 .05 0 0 0 0 0

703 .005 .03 >.05 0 0 0 0 0

704 .002 .001 >.05 0 0 0 0 0

-259-

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TB 1/2 1 2 1/2 1 2

705 .001 .0008i .05 0 0 0 0 0 0

706 .01 .005 >.05 0 0 0 0 0 0

707 .001 .03 >.05 0 0 0 0 0 1

708 .0003 .001 >.05 0 0 0 0 0 0

709 .003 .008 >.05 0 0 0 0 0 0

710 .005 .005 >.05 Ό 0 0 0 0 0

711 .03 .03 >.05 - 0 0 0 0 0 0

712 .001 .002 >.05 0 0 0 0 0 0

713 .002 .002 >.05 0 0 0 0 0 0

^' 714 .008 .003 >.05 0 0 .0 0 0 0

715 .0005 .003 >.05 0 0 0 0 0 0

716 >.05 >.05 >.05 0 0 0 0 0 1

717 .005 .003 >.05 0 0 0 0 0 1

^; 718 .001 .0005 » .03 0 0 0 0 0 0

^~ 719 .002 .001 <.05 0 0 0 0 0 0

720 .002 ,003 .05 0 0 0 0 0 1

- 721 .002 .01 <.05 0 0 0 0 0 0

722 .001 .005 .1 0 0 0 0 0 0

723 >.05 >.05 >.05 0 0 0 0 0 0

724 .002 .01 .05 0 0 0 0 0 0

725 .002 .03 >.05 0 0 0 0 0 0

726 .0005 .OOOS ! .04 0 0 0 0 0 0

"C ^■

Compound Lepidoptericidai Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1

727 .03 .01 .05 0 0 0 0 0

728 .03 .03 .05 0 0 0 0 0

729 .001 .001 .01 0 0 0 0 0

730 .05 >.05 >.05 0 0 0 0 0

731 .000! i .0005 >.05 0 0 0 0 0

732 >.05 >.05 >.05 0 0 0 0 0

733 >.05 >.05 >.05 0 0 0 0 0 1

734 >.003 .12 .05 0 0 0 0 0 0

735 - .01 .008 .1 0 0 0 0 0 0

736 >.05 .4 >.l 0 0 0 0 1 2

737 .01 >.05 >.l 0 0 0 0 0 0

738 >.05 .2 .04 0 0 1 0 1 2

739 >.05 >.05 .05 0 0 1 0 0 1

740 >.05 .1 .04 0 0 .0 0 1 2

741 >.05 .03 .04 0 0 0 0 0 0

742 >.05 .03 .05 0 0 0 0 0 0

743 .05 .0.05 .04 0 0 0 0 0 0

744 >.05 .1 >.05 0 0 0 0 1 2

745 >.05 .05 .05 0 0 0 0 1 2

746 .005 .005 .04 0 0 0 0 0 0

747 .003 .0005 .05 0 0 0 0 0 0

748 .05 .1 >.05 0 0 0 0 0 0

Compouid Le spidoptericidal Phytotoxicity No. Activity Cotton Squash

SMC CL TBW 1/2 1 2 1/2 1 2

749 >.05 .005 >.05 0 0 0 0 0 0

_. 750 .03 >.05 >.05 0 0 0 0 0 0

751 .005 <.001 .05 0 0 0 0 0 0

752 .01 .008 >.05 0 0 0 0 0 2

753 .03 .05 >.05 0 0 0 0 o- 0

754 .005 .03 >.05 _, 0 0 0 0 0 1

755 .003 .05 >.05 0 0 0 0 0 1

756 .008 .03 .05 0 0 0 0 0 1

757 .03 .03 .05 0 0 0 0 1 2

758 .008 .03 .05 0 0 0 0 0 2

759 .01 .15 >.05 0 0 0 0 0 0

760 .006 .01 .05 0 0 0 0 0 0

761 >.05 _. .5 >.05 0 0 0 0 0 0

762 .05 .01 >.05 0 0 0 0 0 0

763 .05 .05 >.05 0 0 0 0 0 0

764 >.05 .03 .05 0 0 0 0 0 0

765 >.05 .05 >.05 0 0 0 0 0 0

766 >.05 .05 .05 0 0 0 0 0 0

767 >.05 .01 >.05 0 0 0 0 0 0

768 .05 .05 ^■ >.05 0 0 0 0 0 0

769 >.05 _{> #0} 5 >.05 0 0 0 0 0 0

770 >.05 .1 >.05 0 0 0 0 0 0

f OMFI

Compound Lepidoptericidai Ph-ytotc>xicity

No. Activity Cotton Squ<ash

SMC CL TBW 1/2 1 2 1/2 3. 1

. 771 .01 .1 >.05 0 0 0 0 0 0

^' 772 .003 .005 .05 0 0 0 0 0 0

773 .01 .005 >.05 0 0 0 0 0 0

774 .0005 .0008 .01 0 0 1 0 0 0

775 .0003 .0004 .003 0 0 1 0 0 2

776 .0005 .001 .05 0 0 1 0 0 1

111 .003 .005 >.05 ^' 0 1 3 0 1 2

118 ^' .0003 .0003 .05 0 0 1 ^• 0 0 1

Symbols for Table II

SMC : salt-marsh caterpillar

CL cabbage looper

TBW : tobacco budworm

> greater than

: less than

OMFI

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, Botr us 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 effective¬ ness 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 conc ntrations, 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

Compound No. Biocides Fungicides LC-100 (ppm) LC-75-100 (ppm) ^'

St ph aureus Botyrytus Bean Powdery Milde cinerea

155 - - 500

166 - - 500

170 - - 500

175 - - 1000

183 5 (10) 500

213 10 500

309 25 10 500

310 - 5 -

662 25 10 -

733 - - 500

769 _ _ 500

( ) = 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 lepidoptericidai activity can be conducted."

OMPI

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 sol¬ vents 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 com¬ prising 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-for ed granule.

-øfUXt/-

These isothiourea compounds can also be formulated to include baits that induce feeding responses in the lepidoptera larva resulting in earlier ingestion of the lepidoptericidai 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 presentl 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.