DD149454A5 - LEPIDOPTERED COMPOSITION - Google Patents

Abstract

The present invention relates to lepidopteric compositions which have, as active compound together with useful carriers and excipients, a compound of the following general formula wherein R, R &sub1; !, R & ind2! and R & ind3! the meaning given in the invention. In general, the lepidoptery extractive compositions of the invention have good efficacy with respect to lepidopterans without, however, exhibiting phytotoxic properties which could damage the crops.

Description

The present invention relates to isothiourea butterflyicide compositions, especially those compositions which do not attack the crops. , ^:

Characteristics of the Known Technical Solutions Isotliuronium 3-chomp tering agent compositions have already been described, in particular in US Pat. Nos. 3,969,511 and 4,062,892. These compounds have the following general formula:

SR, \ ^z

RN = C-NHR,

219743 _ ₂ _

The compounds of these patents have the great disadvantage that they have a high degree of phytotoxic effect. They probably kill the lepidopterans in the crops, but are also harmful to the crops.

Object of the invention

It was thus an object of the present invention to describe new isothiourea butterfly active compound compositions as an active compound which effectively control the lepidopterans without, however, accessing the crops.

Explanation of the essence of the invention

It has been found that the substitution of the active hydrogen on the known isothiuronium and isothiourea compounds described above with some specific, relatively easily cleavable groups decreases or even eliminates the phytotoxic effect of the corresponding compound, but in which the butterfly has a destructive effect, and in some cases even can be improved.

The compounds of the present invention are thus novel compounds which can be described as isothioureas and are active butterfly killers.

The compounds of the present invention can be represented by the following general formula.

SR ₂

RN = C-NR,

I c

^R 3

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

^C 2 ~ ^C 10 ^A - * - kyl, preferably C ₅ -C ₉ alkyl, most preferably

C ₆ -C ₈ alkyl,

C ₂ ^- C ₁₀ alkoxyalkyl, C ₅ -C preferably ₉ alkoxyalkyl, on

•. · '' - ·. '' ^:: . ·· "" - 3 -

219 743 - 3-

bevorzugtesten C ^ -C ₀ alkoxyalkyl, and phenyl and

R and R, together have between 12 and 22 carbon atoms?

wherein R2 is selected from the group consisting of:

C, -Cn * alkyl, preferably C, -C ₆ alkyl, most preferably C ₁ -C ₃ alkyl,

Cj ~ C alkenyl, preferably Ct-Cc alkenyl, most preferably C ₂ -C ₃ alkenyl, C ₃ -C ₄ alkynyl,

^ 2 ~ ^C 4 hydroxyalkyl, preferably C ₃ -C ₃ hydroxyalkyl, C ₃ -C ₆ alkylthioalkyl, preferably C ₃ -C ₄ alkylthioalkyl, C ₂ -C, alkyloxyalkyl, preferably C ₃ -C ₄ alkylthioalkyl, (CH ₂ J _n [ ^x (CH ₂ ) _n ] where n = 1 or 2, X represents 0 or S and y = 1-4, preferably 1-2, 0,

COH wherein n = 1-10, preferably 1-5, preferably

test 1-3, phenyl and phenethyl;

wherein R _{3 is} selected from the group consisting of:

Carboalkoxyalkyl wherein the alkyl is a C, -C. Alkyl, preferably C, -C ₂ alkyl,

Alkylketoalkyl wherein the alkyl is a C, -C ₄ , preferably C ₁ -C ₂ alkyl,

Hydroxyalkenyl wherein the alkenyl is a C ₃ -C ₄ alkenyl, hydroxyalkyl wherein the alkyl is a C ₁ -C ₆ -alkyl, preferably a C ₁ -C -alkyl, most preferably a C ₁ -C ₃ -alkyl,

Formylhydroxymethy1,

Hydroxyhaloethyl wherein halo is chlorine, bromine or iodine, preferably chlorine or bromine, most preferably chlorine

• - 4 -

219743 -4-

stands, . .. '·. '.;'·''.-:.,;''^;":. Substituted phenoxyalkyl wherein the alkyl is a C, -C "alkyl preferably a C, alkyl and the substituents p-methoxy, Cl, NO ₃ or CN,

λ /

\\ 1

^{N in which} R is -OH, -RH ₂ or

1 C ₁ -C. Alkoxy, preferably methoxy,.

OH OH j ι

-CH-CHN-C = NR ₁ where R, R and R _{2 have} the abovementioned R definition,

OH SR - / "Λ I

- (' ^N V-NC = NR, where R, R ₁ and R- are the above-mentioned / L ^L

R have definition, OH

^0Π

-PO ₃ * B, -PO ₂ * B or -SO ₃ 'B where B is a basic cation,

preferably an organic basic cation, most preferably an organic, basic cation selected from the group consisting of: * »

Θ / ΓΛ0

(CH -) - NH and ('NH,

S / ^R 4 -CN where R is selected from the group

Rc standing out:

-H,

-C ₁ -C ₀₀ alkyl, preferably C ₁ -C ₁₀ alkyl, more preferably C, -CG alkyl and at bevorzugtesten C, -CG alkyl, hydroxyethyl, naphthyl, phenyl,

substituted phenyl, wherein the substituents are independently selected from the group. ^: ''. '.' · '''/''''.·.:''-.' · .. ... - 5 - '

19743

consisting of halogen, preferably chlorine, C ₁ -C ₅ alkyl, preferably C, -C ₂ alkyl, C, -C ₅ alkoxy, preferably C, -C ₀ alkoxy, nitro, cyano, and -CFo,

CH

where R, R, and R "have the definition given above,

O SR

Il I ^Λ

- (CH ₂ ) gNHCN-C = NR where R, R ₁ and

Have bene definition, κ

the above-mentioned

CH-

O ^SR 2

CH ₂ NHCN-C = NR ₁

CH. where R, R, and R ₀ are as defined above,

ii

f ^R

NHCN-C = NR where R, R and R _{2 are} the above

have specified definition

O SR ₀ Ii I

NHCN-C = NR,

where R, R and R have the definition given above,

Oil

O It

NHC-O (CH ₀ CH ₀ O) -CNH CH-, CH-

Il I *

NHC-NC = NR ₁

where χ is 1 - 8 and R, R, and have given definition, the above-mentioned

219743

NH (CH ₀ ) -NHCNH

O, ^SR 2

NHC-NC = NR ₁

ι Χ

wherein m is 2 or 3 and R, R ₁ and R- have the definition given above,

H ι

NHC-N-C = NR

where R, R, and R _{2 have} the definition given above,

NHC NH

0 Il

NHCNH

Ii ι

NHC-NC = NR _n

CH.

wherein R, R ₁ and R _{0 have} the definition given above, ^ 0

• l

NHCXR

where X is selected from the group consisting of:

o,::. .. ·; , "'.

NH, and

Y is hydrogen or methyl; and R _{10 is} selected from the group consisting of:

2 19743, ₇ _

Ci-C ₁₀ alkyl, preferably, X Io

C ₁ -C ₀ alkyl, most preferably Io

C ₁ -C ₂ alkyl, ·

C ₃ -C alkenyl, C ₃ -C ₄ alkynyl, C 1 -C ₆ haloalkyl

C ₃ -C ₃ haloalkyl, C ₃ -CgCycloalkyl, C ₇ -C _3n polycycloalkyl, C ₂ -C ,, polyalkoxyalkyl, C ₃ -C ₆ hydroxyalkyl, C ₃ -C _1n alkoxyalkyl, _C3 -CG carboalkoxyalkyl, C ₄ -CG Cycloalkylalkyl, C.-Cg alkylcycloalkyl, preferred

C-Cq ₆ alkylcycloalkyl, C ₄ -C ₇ Cycloalkylimino, C ₂ -C, alkylimino, C, -C ₃ alkylamino, C ₄ -C, - dialkylaminoalkyl Cg-C ₁ cycloalkenyl, phenyl,

Alkylphenyl wherein the alkyl has 1-4 carbon atoms,

Parachloroalkylphenyl wherein the alkyl has 1-4 carbon atoms, naphthyl,

Anthracenyl, '

Benzamidocycloalkyl where the alkyl is a C ₁ -C ₂ alkyl, pyranylmethyl, tetrahydrofurfuryl, thiophenemethyl, benzhydryl, halobenzhydryl, polycyclic alcohol, and substituted phenyl, where the substituents are

197 43

, '. - 8th - . -.; ^; , Are selected from the group consisting of C ₁ -C ₄ alkyl, halogen, nitro,

Trifluoromethyl, formyl, chloroacetyl, C, -C ₄ alkoxy, hydrogen, benzyl, chlorobenzyl, phenethyl, and

substituted phenethyl wherein the substituents are selected from the group consisting of:

C, -C. Alkyl and halogen and R ,, is selected from the group consisting of:

C ₁ -C ₄ alkyl,

C 1 -C 4 alkoxylalkyl, and

C ₃ -C ₄ alkenyl,

R. and R-, together heterocyclic compounds

making,

preferably selected heterocyclic compounds

from the group consisting of:

azepinyl,

morpholinyl,

piperidinyl,

C ₁ -C ₃ alkyl substituted piperdinyl, and

Y is hydrogen or methyl under the condition that if X = 0 or S is R- _{n is} not hydrogen and substituted phenyl in which the substituents are selected from the group consisting of:

Halogen,

C ₁ -C ₄ alkoxy,

phenoxy,

Trifluoromethyl,. C ₁ -C ₆ thioalkyl,

 .-. ' .... '·. 'Λ - .9 -.

43

nitro,

isocyanato,

C ₃ -C ₄ polyalkoxy,

C ₃ -C ₇ cycloalkyl,

C ₃ -C ₃₃ carboalkoxyalkyl, preferably C ₃ -C ₁₀ carboalkoxyalkyl,

C, -Cg haloalkyl, preferably C ₁ -C ₄ haloalkyl,

C 1 -C ₁₂ alkenyl, preferably C ₃ -C ₄ alkenyl,

C ₂ -C ₆ dialkylamino,

phenylamino,

C, -C ₂₄ alkyl, preferably C ₁ -C ₄ alkyl,

C ₃ -C ₁₂ hydroxyalkylamidoalkyl,

C -C-C ₁₀ Ν, Ν-hydroxyalkyl-ureidoalkyl,

Isocyanatoalkyl in which the alkyl is a C ₁ -C ₅ alkyl,

C ₃ -C ₁₂ alkylamidoalkyl,

Polyalkoxyamidoalkyl where

the polyalkoxy moiety has between 3 and 6 repeating C ₂ -C ₃ alkoxy units and the amidoalkyl moiety has between 4 and 12 carbon atoms,

-SO ₂ Cl,

-SO ₂ polyalkoxyamidoalkyl in which the polyalkoxy moiety has between 3 to 6 repeating C ₂ -C ₃ alkoxy units and the amidoalkyl moiety has between 4 and 12 carbon atoms,

R ₁ . is selected from the group consisting of: hydrogen, C ₁ -C ₄ alkyl,

C ₇ -C 12 alkoxyalkyl,

- 10 -

2 197 43

C ₃ -C ₄ alkenyl, hydroxyethyl and phenyl,

wherein R ₄ and R ₅ together form heterocyclic compounds, preferably heterocyclic compounds selected from the group consisting of:

azepinyl,

morpholinyl,

Piperdinyl and

CJC ₃ alkyl-substituted piperdinyl,

o ','. '··' '' .. '

-CX R _c wherein X is O or S is .η is 0 or 1, R _{c is} also η o to o

is chosen from the group consisting of:

C, -C, Q alkyl, preferred

C, -C-2 alkyl, most preferably C ₁ -C ₄ alkyl,

C ₂ -C ₆ haloalkyl, phenyl, and

substituted phenyl wherein if η = 1, the substituents are selected from

the group consisting of: nitro, chloro, C ₁ -C ₂ alkyl, C ₄ -C ₆ polyalkoxyalkyl C ₁ -C ₆ cycloalkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₆ alkoxyalky1,. C - G hydroxyalkyl,

C, -C-, carboxyalkyl, and C ₅ -Cg trialkylammoniumalkyl salts, and if n = 0 the substituents are selected from the group consisting of chlorine,

, Thiokalium,

C, -C, ₈ alkyl, preferably,

1 9743 - ii -

C, -C, 2 alkyl, most preferably C ₁ -C ₄ alkyl, benzyl,

^C 1 ~ ^C 2

C ₂ ^- C. Chlorcarboxyalkyl,

C.-Cg polyalkoxyalkyl, and acetyl,

CR ₇ CY, Z wherein R _{7 is} selected from the group consisting of PUS

where η = 0 to 8

2 η -CH = CH-,

where M is H or Cl, M "

CCl = CCl,

-, and ₂₂ O, and

O-

d = 0 or 1, if d = 1,

Y is selected from the group

out:

-0,

-S, and

NH,

Z is selected from the group consisting of:

^C l ~ ^G l8 ^A - ^L ^ y ¹ 'is preferred

'C ₁ -C ₄ alkyl, most preferably C ₁ -C ₄ alkyl, hydrogen,

C ₄ -CJ ₆ polyalkoxyalkyl, C ₄ -C ₃ dialkylaminoalkyl,

C ₃ -C ₁ alkynyl, ^{J b} - 12 -

219743 - i2 -

phenyl,

substituted phenyl, organic salts, inorganic salts, and if d = 0, Z is selected from Cl or

-NC = NR where R, R ₁ and R ₀

I 1 Δ

R is the above

Have definition 0

_ ρ (R)

Wherein Rg is selected from the group consisting of: C, -C, q alkoxy, preferred

CC ₅ alkoxy, amino, CC ₁₀ alkoxyamino, preferred,

C, -Cc alkoxyamino, hydroxy, and organic base

-SO Rq wherein w = 0-2 and R _{Q is} selected from the group consisting of: amino, C ₁ -C, "alkyl, preferred

C ₁ -C ₅ alkyl,

C ₁ -C ₄ haloalkyl, ^r

phenyl,

C ₁ -C ₁₀ dialkylamino, C, -C, _Q alkylamino, C, -C, _o alkoxy, preferred

substituted phenyl wherein the substituents are selected from the group consisting of nitro, chloro,

C ₁ -C. Alkyl and ¹ . - 13 -

2 197 43 - is -

Methoxy.

The compounds of the present invention are derivatives of isothioureas having a free hydrogen atom on the nitrogen. These isothioureas have the following general formula:

SR

R-N = CNHR

The preparation of the isothioureas is well known in the literature. They are prepared by reacting an isothiocyanate, with a primary amine to thiourea, followed by reaction with an alkyl halide to form isothiourea salt. An inert solvent, such as ethanol, can be used both for the preparation of the thiourea and for the alkylation stage to the isothiourea salt. To increase the reaction rate usually the reaction mixture must be heated. The preparation of Isothioharnstof fsalzes thus takes place according to the following scheme:

R-NCS + H ₂ NR ² -> RNHCNHR ²

SR ¹

R-N = CNHR.HX

^X - ^χ . ^Br or ^C1

The compounds of the present invention are prepared by reacting the base of an isothiourea with an isocyanate or an acid chloride. The free base can be prepared either by neutralizing an isothiourea salt with a cold aqueous solution of a base, such as

- 14 -

2 19743: ₁₄ .

e.g. dilute sodium hydroxide, extract the free isothiourea fbase with a water-insoluble solvent such as hexane, benzene, toluene, etc., dry over a dehydrating agent such as magnesium sulfate, filter and evaporate under vacuum. It is also possible to dissolve the isothiourea salt in an inert solvent such as benzene or toluene and to add equimolar amounts of an isocyanate and equivalent amounts of a soluble tertiary base or acid chloride and two equivalent amounts of a soluble tertiary base such as triethylamine, the reaction being effected by stirring at room temperature during several hours and refluxing for a shorter period of time. If a base such as triethylamine is used, the isothiourea salt may also be treated in a solvent such as benzene in which triethylamine hydrohalide is almost completely insoluble, followed by filtration of the triethylamine hydrohalide and treatment of the filtrate with the isocyanate or acid chloride to complete the reaction described above. Suitable solvents for the condensation of the isothiourea with an isocyanate or an acid chloride are those which are inert under the reaction conditions, i.e., do not react with any of the reactants. Such solvents are hexane, benzene, toluene, tetrahydrofuran, dioxane, methylene chloride, diethyl ether and the like. Depending on the reactants, the reaction temperatures are in a range of about -20 C to 80 C and the reaction times of about 0.5 to 24 hours.

It has been found that the condensation of an Isothioharnstof fes with an isocyanate or an acid chloride can be accelerated by the addition of catalysts such as triethylamine and dibutyltin dilaurate. ,

The reactions described above can be represented as follows:

- 15 -

219743

A) Isothiourea with an isocyanate

2 2

sir sir

• ι 3 I ι

RN = CNHR + R ⁰ NCO -> RN = CN-R

¹ O = CNHR

B) isothiourea salt + base

SR ²

3

RN = CNHR.HX + Et ₃ N + R ^J NC0

SR ²

RN = CNR ¹ O = CNHR ³

HX

C) isothiourea base with an acid chloride

SR ₂

RN = CNHR

R ₃ CCl

SR

RN = CNR ₁ + O = CR ₃

Et ₃ N

HCl

The isothiourea intermediates or precursors can be prepared as described in the art, particularly in US Pat. Nos. 3,969,511 and 4,062,892.

The compounds obtained are effective butterfly killers if they are sprayed in effective amounts on lepitopters, their whereabouts, or their foods. Some of these compounds have a phytotoxic effect so that they could be used both as a herbicide and as a butterflyicide. Some of the compounds, by the way, have biocidal and / or fungicidal effects.

Effective amounts are understood to mean an amount of the butterfly control composition such that, when applied in a satisfactory manner, these compositions

- 16 -

219743: ₁₆ .

binding to the place of residence of the lepidopteran, the foodstuffs of the same or on the insects an effective control or dying or significant injury of a large part of the Lepidoptera is obtained.

The compounds of the invention are useful for protecting food / fiber, edible crops, ornamental plants by insect damage and lepidopteran larvae. Examples of such crops that can be protected are trees such as oak and conifer, fruit trees such as peach, apple and walnut, vegetables such as tomatoes, other crops such as tobacco, cotton, lettuce, cabbage, corn and rice, and any other crops from which the lepidopterans feed ,

embodiments

For a better understanding of the invention reference is made

to the following examples.

The novel compounds of the present invention can be prepared starting from the precursors and intermediates described above by well-known methods according to the following examples.

example 1

1,3-Diheptyl-2-ethyl-3- (0,0-dimethylphosphorus) isothiourea

6.0 grams (g) (0.02 moles) of 1,3-diheptyl-2-ethylisothiourea and 200 milliliters (ml) of methylene chloride were combined in a 500 ml 3-necked flask equipped with stirrer, thermometer and dropping funnel. The solution was stirred and cooled to ⁰ ° C. 2.0 g (0.02 mol) of triethyramine were added to the flask, followed by 3.0 g (0.02 mol) of phosphorus oxychloride dissolved in 25 ml of methylene chloride. The phosphorus oxychloride was added so that the temperature in the flask could be maintained at about 0-5 ° C. After completion of the addition, the reaction mass was stirred at 0 ° C for 30 minutes. , '. '.-. , '"- 17 -

2197 43 _ ₁₇ _

The solution was then treated with 8.7 g (O, O4 mole) of a 25% sodium methoxide solution in methanol with 25 mL of methylene chloride over a period of 15 minutes keeping the temperature at 0-5 ° C. The reaction mixture was stirred at 5 ° C for 30 minutes and then at room temperature for 30 minutes. The resulting mixture was washed twice with 200 ml of water and the phases were separated. The methylene chloride phase was dried with anhydrous MgSO ₄ , filtered and the solvent evaporated in vacuo to give 7.4 g of the desired product, 1,3-diheptyl-2-ethyl-3- (0,0-dimethylphosphor) isothiourea having a refractive index η of 1.4528 were obtained. The product

13 was confirmed by IR, H-NMR and C-NMR spectroscopy.

Compound No. 229 in Table I.

Example 2

1,3-diheptyl-2-ethyl-3-N-C4-methyl-3- (carbowax-350-carbamyl) H

phenylcarbamylisothiourea This compound was prepared as follows:

Intermediate a)

3.56 g (0.02 mol) of 2-methyl-5-nitrophenyl isocyanate, 7.0 g (0.02 mol) of Carbowax 350, 2 drops of triethylamine, 1 drop of di-butyltin dilaurate and 25 ml of methylene chloride were added with stirring given a 100 ml flask together. After completion of the exothermic reaction, the solvent was evaporated in vacuo. The residue was dissolved in a 10: 1 diethyl ether-toluene mixture. A white solid impurity was removed by filtration and the filtrate was vacuum-treated to give 10.5 g of the desired compound N- (2-methyl-5-nitrophenyl) -carbowax (350) -carbamate having a refractive index n_ of 1.4810 receive. The structure was confirmed by C-NMR spectroscopy.

Intermediate b)

7 g (0.013 mol) of the intermediate a) were dissolved in 200 ml

- 18 -

219743

Ethanol dissolved in a Parr glass pressure bottle. 1 g of palladium on carbon support was added as a catalyst and the mixture was shaken and hydrogenated at pressure

2

of 3.52 kg / cm for 30 minutes. The reaction mixture was filtered and the filtrate was evaporated in vacuo to give 6.0 g of the desired compound N- (2-methyl-5-amino-phenyl) -carbowax (35O) -carbamate. The structure was confirmed by C-NMR spectroscopy.

Intermediate c)

5.8 g (0.0116 mol) of the intermediate b) were in 200 ml of toluene in a 250 ml 3-necked flask equipped with condenser, stirrer and gas inlet tube together. The solution was stirred, warmed to 70 ° C and saturated with HCl gas. The mixture was then heated to reflux and phosgene was introduced for 30 minutes. The reaction mass became clear. N gas was then introduced to remove excess phosgene. The solvent was removed in vacuo to give 6.1 g of N- (2-methyl-5-isocyanophenyl) -carbowax <35O) -carbamate, having a refractive index η of 1.5848. The structure was confirmed by C NMR spectroscopy.

1,3-Diheptyl-2-ethyl-3-N-f4-methyl-3- (carbowax-350-carbamyl) * f phenylcarbamylisothiourea

2.0 g (0.004 mol) of the intermediate c), 1.2 g (0.004 mol) of 1,3-diheptyl-2-ethyl isothiourea, 2 drops of triethylamine and 15 ml of methylene chloride were added together in a 100 ml flask. After completion of the exothermic reaction, the solvent was removed in vacuo to give 3.3 g of the desired product, 1,3-diheptyl-2-ethyl-3-N-yl-methyl-3- (carbowax-350-carbamyl) -1 - phenylcarbamylisothiourea

13 were holding. The structure was determined by C-NMR spectroscopy

approved. Compound No. 216 in Table I.

- 19 -

2197 43 _ ₁₉ _

Beis piel3

l, 3-Diheptyl-2-ethyl-3- [ν- (3-tergitol (15-S-7) oxycarbamyl]

phenyl) carbamyl isothiourea The compound was prepared as follows:

Intermediate d)

The procedure of Example 2 Intermediate a) was repeated with 3.28 g (0.02 mol) of 3-nitrophenyl isocyanate, 10.1 g of tergitol (15-S-7), 2 drops of triethylamine and 25 ml of methylene chloride to give 13.2 g of the desired compound N- (3-nitrophenyl) -tergitol (15-S-7) -carbamate. The structure was confirmed by IR spectroscopy.

Intermediate e)

The procedure of Example 2 Intermediate b) was repeated., 11.2 g (0.0166 mol) of intermediate d) were reduced with H ₂ in ethanol in the presence of 1 g of palladium on carbon black catalyst, giving 9.3 g of the desired compound N- 3-aminophenyI) -tergitol (15-S-7). carbamate was obtained, -. The structure was confirmed by IR spectroscopy.

Intermediate f)

The procedure of Example 2 intermediate c) was repeated. 9.3 g (0.0145 mol) of intermediate e) were treated with excess FICl gas followed by an excess of phosgene, giving 9.4 g of the desired compound N- (3-isocyanophenyl) -tergitol (15-S-7) - carbamate were obtained. The structure was confirmed by IR spectroscopy.

l / 3-DiFie'ptyl-2-ethyl-3- [N- (3-tergitol (15-S-7) oxycarbamyl p'-qyl] - cabamyl-j-isothiourea f

The / learned from Example 2 was repeated. 2g (0.003 mol) of intermediate f) ^; with 0.9 g (0.003 mol) of 1,3-diheptyl-2-ethyl isothiourea, 2 drops of triethylamine and 10 ml of methylene chloride, whereby 2.9 g of the desired product, 1, 3-diheptyl-2-ethyl-3- [n- (3-tergitol- (15-S-7) -oxycarbamylphenyl) carbamyl] isothiourea with a

- 20 -

219743

Refractive index n _n of 1.5710 were obtained. The structure was confirmed by IR spectroscopy. Compound No. 219 in Table I.

Example 4

1, 3-Diheptyl-2-ethyl-3- (0,0-diethylphosphorodithioylacetyl) -isothiourea intermediate g)

30 g (0.1 mol) of l, 3-diheptyl-2-ethyl isothiourea, 12.4 g (0.11 mol) of chloroacetyl chloride and 250 ml of toluene were provided in a 500 ml 3-neck flask equipped with stirrer, thermometer and dropping funnel brought together. The solution was stirred and cooled to -30 ° C on a dry ice bath 11. 11 g (0.11 mol) of triethylamine were added over a period of 30 minutes After completion of the addition, the reaction mixture was brought to room temperature and continued for one hour The reaction mixture was then washed twice with 200 ml of water, 100 ml of saturated sodium bicarbonate solution and finally with 200 ml of water. The toluene phase was dried with anhydrous MgSO4, filtered and evaporated in vacuo to give 36.1 g of the desired compound 1.3. The structure was confirmed by IR and NMR spectroscopy.

1.3 Dihepty1-2-äthy1-3- (0,0-diäthylphosphorodithioy! Acetyl) isothiourea

2, 2 g (0.012 mol) of 0,0-Diäthyldithiophosphorsäure were dissolved in 25 ml of acetone and treated with 5 g of anhydrous potassium carbonate. After neutralization, the acetone phase was decanted into a 250 ml flask containing a solution of 3.0 g (0.008 mol) of the intermediate g) in 75 ml of acetone. The resulting mixture was stirred at room temperature for two hours and poured into 200 ml of toluene. The mixture was washed twice with 200 ml of water. The toluene phase was then washed with anhydrous MgSO 4. dried, filtered and evaporated in vacuo whereby 3.6 g of the desired product 1,3-

. '':':'' - 21 -

219743

-S- (Ο, Ο-diethylphosphorodithioylacetyl) isothiourea having a refractive index n _n of 1.5060. The structure was confirmed by IR and NMR spectroscopy. Compound No. 261 in Table I.

Example 5

NfN'-Diheptyl-S-ethyl-N-propanesulfonylisothiourea 1.8 g (0.018 mol) of triethylamine were added to 4.5 g (0.015 mol) of N, N- ^1- thiheptyl-S-ethyl-isothiourea in 50 ml of methylene chloride in a stirred Given the piston. The mixture was added dropwise at 0 ° C with a solution of propanesulfonyl chloride (0.018 mol, 2.6 g) in 8 ml of methylene chloride. The mixture was stirred for 1.5 hours at room temperature and then for 1.5 hours at 30-35 ° C. The cooled solution was washed twice with 20 ml, once with 25 ml of saturated sodium bicarbonate solution and twice more with 20 ml of water washed. The organic phase was dried over magnesium sulfate and evaporated in vacuo to give the product, a yellow OeI with a refractive index η of 1.4805. The yield was 5.2 g (85.4% of theory). The structure was confirmed by IR spectroscopy. Compound No. 203 in Table I.

Example 6

N, N'-Diheptyl-S-ethyl-N'-p-toluenesulfonylisothiourea The reaction was carried out with 0.018 mole (3.4 g) of p-toluenesulfonyl chloride as described in Example 5. The product had a refractive index η of 1.517. The yield was 6.0 g (88% of theory). The structure was confirmed by IR / NMR and mass spectroscopy. Compound No. 206 in Table I.

Example 7

1 , S-di-n-heptyl-l-trichloromethylthio ^ -ethyl-isothiourea

3 g (0.01 mol) of 1,3-di-n-heptyl-2-ethylisothiourea were mixed with 50 ml of tetrahydrofuran in a stirred flask,

- 22 -

219743 ₂₂ _

which was cooled on an ice bath, mixed. 1.4 ml (0.01 mol) of triethylamine were added and the mixture was stirred for 10 minutes. The mixture was then added dropwise over 2 minutes with 1.1 ml (0.01 mol) of trichloromethylsulfenyl chloride. A white precipitate was obtained and the mixture was stirred for 1 hour, bringing sae to room temperature. The resulting reaction mixture was allowed to stand overnight. The mixture was filtered to remove the white solid. The solid was washed twice with 10 ml of fresh tetrahydrofuran. The filtrate was evaporated in vacuo to give 4.55 g of the desired product at a yield of 101.2%. The resulting liquid had a refractive index n_ of 1.5084. The structure was confirmed by IR mass spectroscopy. Compound No. 29 7 in Table 1.

Example 8

1,3-di-n-heptyl-1- (2'-fluoro-1 ', 1', 2 ', 2'-tetrachloroethylthicf-2-ethylisothiourea .

2.0 g (0.007 mol) of 1,3-di-n-heptyl-2-ethylisothiourea was dissolved in 100 ml of tetrahydrofuran and placed in a stirred flask on an ice bath. 0.7 g (0.0069 mol) of triethylamine was added and the mixture was stirred for 10 minutes. The mixture was then treated with 1.68 g (0.0068 mol) of 2-fluoro-1,1,2,2-tetrachloroethylsulfenyl chloride dissolved in 20 ml of tetrahydrofuran over 15 minutes. A precipitate was obtained. The mixture was stirred for 2 hours. The mixture was then filtered and the precipitate washed twice with 20 ml of tetrahydrofuran. The filtrate was evaporated in vacuo to give the desired product in a yield of 3.5-3 g with a refractive index η of 1.5091. The product was confirmed by IR and mass spectroscopy. Compound No. 29 8 in Table 1.

- 23 -

2197 43

- 23 -. _ .. ··. - · '-. Example 9

1, S-Di-n-heptyl- 1 -nitrophenylthio-1-thylisothiourea 1 »9 g (0.01 mol) of 2-nitrobenzenesulfenyl chloride were dissolved in 50 ml of tetrahydrofuran. A mixture of 3 g (0.01 mol) of 1,3-di-n-heptyl-2-ethylisothiourea in 30 ml of tetrahydrofuran was added and the mixture was placed in a round bottom flask on an ice bath. "1.05 g (0.01 The reaction mixture was stirred in the ice-bath for 3 hours while the temperature rose to room temperature J. The mixture was then filtered and the filtrate was evaporated in vacuo a slightly brown sticky residue was obtained. The residue was dissolved in about 100 ml of diethyl ether and concentrated on magnesium sulfate and decalite 4200. The filtrate was evaporated in vacuo to give 4.2 g of a liquid having a refractive index η of 1.546 3. The product was confirmed by IR spectroscopy. Compound No. 300 in Table I.

Example 10

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

'.'"3g (0.01 mole) of S-ethyl-l-3-diheptyl-2-isothiourea 3 g (0.03 mol) of ethyl acrylate were placed in a 100 ml glass bottle. A catalytic amount of a base (0.1 g NaOH) was added and the mixture heated from 25 to 85 ° C. The mixture was kept at 85 ° C. for 5 hours. The reaction mixture was then cooled and treated with 150 ml of ether.

The ether was washed with 100 ml of water, dried and evaporated to give 2 g of the desired compound. The structure was confirmed by IR and NMR spectroscopy. Compound No. 199 in Table I.

- 24 -

2197 43

Example 11

S-ethyl-1,3-diheptyl-3- (3-oxobutyl) -2-isothiourea The procedure of Example 10 was repeated except that ethyl acrylate was replaced with methyl vinyl ketone and the reaction was conducted at room temperature for 4 hours. The processing of the product was the same. 2 g of the desired compound were obtained. The structure was confirmed by IR and NMR spectroscopy. Compound No. 200 in Table I.

Example 12

N, N-di-n-Hepty1-N'-ethyl oxalyl-S-ethyl-isothiourea 5.0 g (16.6 millimoles) S-ethyl-1,3-diheptyl-2-isothiourea 1.8 g (18, 3 millimoles) of triethylamine in 50 ml of methylene chloride were mixed in a 100 ml one-necked round bottom flask equipped with magnetic stirrer and stopper. The clear, slightly yellow solution was cooled to 0 C on an ice bath. To this stirred, cooled solution was added dropwise 2.50 g (18.3 millimoles) of ethyl oxalyl chloride while maintaining the temperature between 5 and 15 ° C. A large amount of white precipitate was formed in seconds. The mixture was stirred for a further hour at 0 ° C. The cooling bath was removed and the mixture was stirred at room temperature for 3 hours. The precipitate was dissolved by adding 50 ml of water and the mixture was added to a separatory funnel containing 50 ml of methylene chloride. The layers were separated and the organic phase 1 time with 10 mL of saturated NaHCO _3, 3MaI with 10 ml of water, saturated sodium chloride and 1 times 10 ml and over Na SO. dried. The dried, clear, yellow, organic solution was filtered over Na ₃ SO ₄ and the solvent removed in vacuo to give 6.63 g (99.7% yield) of the desired compound, a clear, yellow OeI with a refractive index η of 1, The product was confirmed by IR and NMR spectroscopy and mass spectroscopy. Compound No. 671 in Table I.

2197 43

- 25 - '..,.:. ,, .. _ Example 13

Bis-N '- (N, N'-n-heptyl-S-ethylisothioureyl) oxalate The procedure of Example 12 was repeated except that instead of the 100 ml round bottom flask a 200 ml round bottom flask was used and 1.16 A clear, yellow solution was obtained which was stirred for one hour at 0 ° C and then for 20 hours at room temperature, the clear yellow solution then being collected in a separating trichlor The phases were separated and the organic phase washed once with 10 ml of 10% potassium carbonate 5 times with 10 ml of water, once with 10 ml of saturated sodium chloride and dried over Na ₃ SO ₄ The organic solution was filtered and the solvent removed as described in Example 12. The yield was 5.55 g (102.1% of theory) of an orange-colored oil with a refractive index index η of 1.4932. The structure of the product was confirmed by IR and NMR spectroscopy as well as mass spectroscopy. Compound No. 688 in Table I.

Example 14

N, N'-di- (1-heptyl) -N '- (äthy mercapto-carbonyl!) -S-äthyIisothioharnstoff

The procedure of Example 12 was repeated except that 5.0 g (16.6 millimoles) of N, N'-di- (1-heptyl) -S-ethyl isothiourea and 1.85 (18.3 millimoles) of triethylamine and 50 ml of methylene chloride in the flask were followed followed by 2.28 g (18.3 millimoles) of ethyl thiochloroformate. The phase of the product obtained was separated, washed and dried as described in Example 12. The solvent was removed in vacuo to yield 6.55 g (101.5% of theoretical yield) of a yellow oil having a refractive index n _D of 1.4922. The structure of the product was determined by IR and NMR spectroscopy and mass spectrometry.

- 26 -

2197 43

- 26 '-, ... -': .. * ·. : Spectroscopy confirmed. Compound No. 300 in Table I.

Example 15

l, 3-Diheptyl-2-ethyl-3- [3 '- (2 "-athoxy-thoxycarbony! amino) -

4'-methylphenylaminocarbonyU isothiourea The compound was prepared as follows:

Stage a) 1,3-Piheptyl-2-ethyl-3- (3-isocyanato-4-methylphenylaminocarbonyl) isothiourea (intermediate).

125 ml of methylene chloride were pipetted under argon into a 200 ml stirred 3-neck flask; 15.1 g (0.86 mol) of toluene-2,4-diisocanate were then added to methylene chloride. 25.8 g (0.086 mol) of 1,3-diheptyl-2-ethyl isothiourea were added without cooling for 5 minutes. The temperature increased from 20 to about 30 C during this addition. The reaction mixture was then heated to reflux (41C) and refluxed for 1 hour. The resulting reaction mixture was concentrated in a rotary evaporator under high vacuum. 39.8 g of a product with a refractive index η of 1.4318 were obtained. The structure

_L3

door of the intermediate was confirmed by IR and C "NMR spectroscopy.

Stage b) Preparation of 1,3-Diheptyl-2-ethyl-3-Γ_3 '- (2'-ethoxyathoxycarbonylamino) -4'-methylphenylaminocarbonyl] -isothiourea.

4.74 g (0.010 mol) of the intermediate from step a) 0.95 g (0.0105 mol) of 2-ethoxyethanol, 2 drops of triethylamine, 1 drop of dibutyltin dilaurate and 25 ml of tetrahydrofuran were dried over a Linde molecular sieve 3A in a 3- Given a neck flask. The mixture was heated to reflux (67-68 ° C) and refluxed for two hours The solvent was heated under high vacuum at a pressure of 0.3 mm Hg or less and at a bath temperature of 80-90 ° C. 5.6 g of a viscous

· ^':' * ''. . ' · - 27 -

2197 43

Oils were obtained. The structure of the product was confirmed by IR and Cl3 NMR spectroscopy. Compound No. 419 in Table I.

Example 16

l _/ ^{3-diheptyl-2-ethyl-3-t} ü - (3 '' -chloro-4 '' -methylphenyl- ureido) -4 '-methylphenylaminocarbonylj-isothioharnstof f. The reaction and the reactants were identical to those of Example 15b) except that 1.49 g (0.0105 mol) of 3-chloro-4-methylaniline was used instead of 2-ethoxyethanol. An insoluble by-product was formed which was removed by filtration before evaporation of the solvent. 3.5 g of the desired product were obtained. The structure was confirmed by IR and NMR spectroscopy. Compound No. 429 in Table

Example 17

1,3-Diheptyl-2-ethyl-3-, 3'-propylurido-4'-methylphenylaminocarbonyl-isothiourea

4.74 g (0.010 mol) of the intermediate product prepared according to Example 15 a) and 2 5 ml of dry tetrahydrofuran were introduced into a 3-necked flask. 0.62 g (0.0105 mol) of propylamine was added at room temperature without cooling. The reaction was exothermic and the temperature increased from 10 to 20 ° C. The mixture was not heated and the reaction was complete after 1 hour. The mixture was filtered to remove a small amount of a solid by-product and worked up as described in Example 15b). 5.0 g of a liquid with a refractive index n "of 1.5312 was obtained. The structure was confirmed by IR and C ¹³ NMR spectroscopy. Compound No. 431 in Table I.

Example 18

1, 3-diheptyl 1-2-ethyl-1-3 ^ 3'-p-chlorobenzylthiocarbonylarrtino-

4'-methylphenylaminocarbonyH isothiourea

The reactants were the same as in Example 15b)

: - 28 -

2197 43

with the exception that 1.66 g (0.0105 mol) of 4-chlorobenzylmercaptan were used instead of 2-ethoxyethanol. 6.5 g of a viscous liquid, the desired product, was obtained. The structure was confirmed by IR and NMR spectroscopy. Compound No. 433 in Table

Example 19 ; -'-,:. : .-:

1, S-diheptyl-a-ethyl-S- (3'-phenoxycarbonylamino-4'-methyl-

phenylaminocarbonyl) isothiourea

The reactants were the same as described in Example 15b) except that 0.99 g (0.0105 mol) of phenol was used instead of 2-ethoxy-ethanol. 5.2 g of a liquid with a refractive index η of 1.5488 were obtained. The structure of the desired product was confirmed by NMR and IR spectroscopy. Compound No. 452 in

Table I. Example 20

1-octyl-2-ethyl-3-sec-heptyl-3-r3- (1-octyl-2-propyl-3-sec-kheptyl-3-carbonylamino) -4-methylphenylcarbonylamino-1-isothiourea

Stage a) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3- (3-isocyanato-4-methylphenylaminocarbonyl) isothiourea intermediate).

This intermediate was prepared as the intermediate in Example 15a) except that 2 7.2 g (0.086 mol) of 1-octyl-ethyl-S-sec-heptyl-isothiourea was used in place of the thiourea reactant from step 15a) were. 41.5 g (9.8% by weight of theory) of a liquid and a refractive index η of 1.5280 were obtained. The desired intermediate was confirmed by IR and C ^ ³ NMR spectroscopy.

Step b) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3 - (1-octyl-1-propyl-S-sec-heptyl-S-carbonylamino) -4-

- 29 -

219743 _ "._

methylphenylcarbonylaminojisothioharnstoff.

The compound was prepared as described in Example 15 b) with the exception that 4.87 g (O, Q10 mol) of the intermediate product prepared in stage 2 Oa) were used and 3.29 g (0.010 mol) of 1-octyl-2 propyl-3-sec-heptyl isothiourea. 7.9 g (96-, 3% by weight of theory) of a liquid having a refractive index n _n of 1.5185 were obtained. The structure of the desired product was confirmed by IR and C ¹³ NMR spectroscopy. Compound No. 558 in Table I.

Example 21

1,3-bis-n-heptyl-1- (carbamylsulfonyl chloride) -2-S-ethylisothiourea

50 ml of dry methylene chloride and 8.49 g of chlorosulfonyl isocyanate (Aldrich) were placed in a 200 ml flask equipped with magnetic stirrer, thermometer and dropping funnel. A solution of 18 g of 1,3-diheptyl-2-ethylisothiourea (100 ml of dry methylene chloride) was added dropwise over 40-45 minutes. The reaction was slightly exothermic so that the flask was cooled in a water bath to maintain the temperature at 28 ° C. The solution was then stirred at 25 ° C overnight.

The solution was filtered and the filtrate concentrated under reduced pressure. 26.2 g (99% by weight of theory) of a thick liquid with a refractive index n _D of 1.4833 were obtained. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 6 35 in Table I.

Example 22

l, 3-bis-n-heptyl-1-chlorocarbonyl-2-ethylisothiourea 100 ml of dry CH ₂ Cl _{2 was} added to a 500 ml thermometer-dropping flask which had been cooled to 5 ° C. on an ice-bath. A solution

, - 30 -

219743

Phosgene in benzene (170 g of 17.5 weight percent concentration) was added. The mixture was then treated dropwise with a solution of 100 ml of dry CH ₂ Cl ₂ , 10.1 g of triethylamine and 30 g of 3-diheptyl-2-ethyl-isothiourea at 5 ° C over 1 hour. The mixture was stirred at room temperature overnight.

The next morning, the reaction mixture was heated to about 40 C for 2 1/2 to 3 hours to ensure a complete reaction. The mixture was then exposed to a reduced pressure to the CH ₀ Cl ₉ to remove solvent. 100 ml of dry ether were added and the mixture was filtered with suction on a glass frit. The solvent was washed with a little ether and the combined filtrates concentrated under reduced pressure to remove the ether. 38.6 g of a liquid (106% by weight of theory) having a refractive index η of 1.4613 were obtained. The structure of the desired product was confirmed by mass spectroscopy. Compound No. 6 43 in Table I.

Example 23

1, 3-bis-n-heptyl-l diet . Hycarbamyl-2-ethylisothiourea 100 ml of dry benzene and 5.44 g of 3-diheptyl-2-ethylisothioureacarbamyl chloride were placed in a 200 ml flask equipped with thermometer and dropping funnel. The mixture was added dropwise with 12 ml of dry benzene and 2.19 g of diethylamine over 10 to 12 minutes. The reaction was slightly exothermic and the temperature increased from 21 to 30 ° C. The mixture was then heated to 45-50 ° C for 3 hours. The reaction mixture was cooled to 15 ° C and washed twice with 50 ml of cold water each time. The benzene phase was dried over MgSO ₄ , filtered and the solvent removed under reduced pressure. 5.75 g of a liquid (96% by weight of theory) having a refractive index η of 1.4568 were obtained. The structure of the desired compound was

- 31 -

219 7 43

- 31 -, - '' '- -' 'confirmed by mass spectroscopy Compound No. 644 in Table I.

Example 2 4

1,3-bis-n-heptyl-l- (propargyloxycarbonyl) -2-ethyl-isothiourea

SO ml of dry tetrahydrofuran and oil, 36 g NaOH were added to a 200 ml flask equipped with thermometer and dropping funnel. A solution of 10 ml of dry tetrahydrofuran and 0.84 g of propargyl alcohol was added dropwise over 8 to 10 minutes. The reaction was slightly exothermic with formation of hydrogen. The mixture was stirred for 3 hours to give a complete reaction.

The reaction mixture was then treated dropwise with 15 ml of dry THF and 5.44 g of 1,3-diheptyl-2-ethyl-isothioureacarbamyl chloride for 10 minutes. The mixture was stirred for 2 hours and warmed to 45 ° C. The reaction mixture was cooled to 25 C and filtered with suction on a glass frit and filter. The solvent was removed under reduced pressure. 5.0 g of a liquid (88% by weight of theory) having a refractive index ή of 1.455 3 was obtained. The structure of the desired compound was confirmed by NMR spectroscopy. Compound No. 648 in Table I.

Example 25

1,3-bis (2-ethylhexyl) -1- (succinic anhydride adduct) 2-

ethyl-isothiourea · Et ^ N salt.

200 ml of dry CH ₂ Cl ₂ , 32.3 g of 1,3- (2-ethylhexyl) -2-ethylisothiourea, 11 g of succinic anhydride and 11.1 g of Et-jN were added to a 500 ml flask. A slight exothermic reaction was observed in the mixing of the components. The solution was allowed to stand overnight.

The reaction mixture was then evaporated under reduced pressure. 47.3 g of a liquid (89 percent by weight

- 32 -

219 7 43

theory) with a refractive index η of 1.4899 were obtained. The structure of the desired compound was confirmed by IR and NMR spectroscopy. Compound No. 665 in Table I.

Example 26

Reaction product of 2 moles of 1,3-di- (2'-ethylhexyl) -2-S-ethylisothiourea + toluene-2,4-diisocyanate In a 200 ml three -necked flask equipped with magnetic stirrer, 3.28 g (0.01 mol) of 1 , 3-di- (2 ^I ethyl-hexyl) -2-S-ethyl isothiourea was mixed with 20 ml of tetrahydrofuran. To this solution was added 0.87 g (0.005 mol) of toluene-2,4-diisocyanate. The temperature rose from 23 ° C to 34 ° C. The mixture was allowed to stand at room temperature overnight and evaporated in vacuo. Infrared analysis revealed that the reaction was not complete. The mixture was thus dissolved in 30 ml of methylene chloride and treated with 1 drop of dibutyltin dilaurate and 2 drops of triethylamine. The homogeneous solution was stirred at room temperature for 1.5 hours. The mixture was evaporated once more under vacuum to give the product as a viscous yellowish liquid with a refractive index n_ of 1.5201. The yield was 4.3 g. IR and NMR spectroscopy confirmed that it was the desired compound. Compound No. 85 in Table I.

Example 27

1,3-di-n-heptyl-l-N-phenylcarbamyl-2-S-n-propyl-isothiourea

The plant described in Example 26 was used. 6.2 g (0.014 mol) of 1, S-di-n-heptyl-S-n-propyl-isothiuronium. Hydrogen iodide was dissolved in 35 ml of tetrahydrofuran and 1.68 g (0.014 mol) of phenyl isocyanate were added followed by a portionwise addition of 1.43 g (0.014 mol) of triethylamine with cooling. A solid precipitated after the addition of triethylamine. The reaction mixture

:. ; '''.' ^: . - 33 - ''

2t9743

was stirred at room temperature overnight. The reaction

- ^ v '-' ·. '·. ". ''- ·· ♦ mixture was then evaporated to remove tetrahydrofuran, the residue was dissolved in chloroform and washed twice with 100 ml of water The organic phase was separated, filtered, dried over magnesium sulfate and evaporated in vacuo to remove the chloroform...? 5.9 g (96.7% by weight of theory) of a yellow liquid having a refractive index η of 1.5188 were obtained and confirmed by IR and NMR spectroscopy that it was the desired compound Compound No. 11 in Table I.

Example 28

1,3-di-ri-heptyl-l-N-octadecylcarbamy1-2-S-ethyl-isothiourea

The plant described in Example 26 was used. 4.5 g (0.015 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea was mixed with 40 ml of tetrahydrofuran and replaced with 4.43 g (0.015 mol) of N-octadecyl isocyanate. 3 drops of triethylamine were added and the mixture allowed to stand overnight. The mixture was then heated to 40 ° C for 20 minutes to ensure a complete reaction. A small amount of a solid formed on cooling and was filtered off. The reaction mixture was evaporated in vacuo to give 8.9 g (100% of theoretical yield) of a pale liquid of refractive index η 1.4750. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 29 in Table I.

Example 29

1, S-di-n-heptyl-1-N-methylthiophenylcarbamyl-S-ethyl isothiourea

The plant described in Example 26 was used.

3.0 g (0.01 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea were mixed with 25 ml of methylene chloride. 2 drops

- 34 -

219743

Triethylamine and 1 drop of dibutyltin dilaurate were added and the mixture with 1.65 g (O, 01 mol) of 4-methylthiophenyl isocyanate. The temperature rose from 23 ° C to 33 ° C. The reaction mixture was evaporated in vacuo to remove methylene chloride to give 4.65 g (100% of theoretical yield) of a yellow liquid with a refractive index n_ of 1.5340. The liquid solidified on standing to a semi-solid product. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 47 in Table I.

Example 30

!, S-di-n-heptyl-l-N ^ -chloräthylcarbamyl ^ -S-ethyl-isothiourea

The plant, process and reactants of Example 29 were used except that 1.06 g (0.01 mole) of 2-chloroethyl isocyanate instead of 4-methylthiophenyl. isocyanate were used. 4.14 g (102% by weight of the theoretical yield) of a clear liquid with a refractive index n _D of 1.4930 were obtained. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 48 in Table I.

Example 31

1-sec-heptyl-3-n-heptyl-2-S-ethyl-isothiourea (intermediate)

The plant described in Example 26 was used. 11.5 g (0.1 mol) of 2-aminoheptane were mixed with 50 ml of ethanol 2B and treated with 15.7 g (0.1 mol) of N-heptyl isothiocyanate an exothermic reaction was obtained during which the temperature of 25 rise to 65 C The was refluxed on a steam bath for 1.5 hours. 17.16 g (0.11 mol) of ethyl iodide were added and the mixture was refluxed for 1.5 hours on a steam bath. The product was evaporated in vacuo to give 44.0 g of an isothiuronium salt. The isothiuronium salt

219743 ₃₅ _

was dissolved in 200 ml of toluene and washed with 100 ml of 5% sodium hydroxide solution. The toluene layer was washed twice with 150 ml of water, dried over magnesium sulfate, filtered and evaporated in vacuo. The residual solvent was then removed under high vacuum to yield 7.78 g (92.6% by weight of the theoretical yield) of clear, yellow liquid with a refractive index η of 1.476. IR and NMR spectroscopy confirmed that it was the desired product.

Example 32

1-sec Hepty1-3-n-hexy1-2-S-ethylisothiourea (intermediate)

The plant, process and reactants of Example 31 were used except that 10.01 g (0.07 mol) of n-hexyl isothiocyanate, 8.05 g (0.07 mol) of 2-aminoheptane, 35 ml of ethanol 2B, 11.7 g (0.075 mol) of ethyl. , iodide, 200 ml of toluene and a 1 wt% solution of sodium hydroxide (0.08 mol) were used as the reactant. 19.6 g (98 percent by weight of the theoretical yield) of a clear liquid with a refractive index n_ of 1.4765 were obtained. IR and NMR spectroscopy confirmed that it was the desired product.

Example 33

1,3-di-n-Hepty1-1-N-tert-butylcarbamyl-2-S-ethyl-isothiourea

The system described in Example 25 was used.3 / Dg (0.01 mol) of 1, S-di-n-heptyl-S-ethylisothiourea were mixed with 30 ml of methylene chloride. Two drops of triethylamine and one drop of dibutyltin dilaurate were added, followed by 1.0 g, (0.01 mole) of tert-butyl isocyanate. The temperature rose from 2 4 to 39 ° C. The reaction mixture was stirred overnight at room temperature and then heated to 35-40 ° C for half an hour around the reaction

219743 - 36 -

to complete. The reaction mixture was evaporated in vacuo to give 3.83 g (96% by weight of the theoretical yield) of a clear liquid with a refractive index η of 1.4750. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 40 in Table

Example 34

1, 3-di-n-heptyl-1-N-ethylacetatecarbamyl-2-S-ethyl-1-isothiourea

The procedure, equipment and reactants of Example 33 were used except that 1.29 g (0.01 mol) of ethylisothiocyanate acetate was used instead of tert-butyl isocyanate. 4.3 g (100 percent by weight of theory) of a clear liquid with a refractive index η of 1.848 was obtained. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 41 in Table I.

Example 35

1, S-di-n-heptyl-S-B-hydroxyethylcarbairyl-methylcarbamyl-S-ethylisothiourea

The plant described in Example 26 was used. 9.0 g (0.03 mol) of 1,3-di-n-heptyl-2-S-ethylisothiourea were mixed with 30 ml of methylene chloride and the mixture was admixed with 3.87 g (0.03 mol) of ethyl cyanoacetate. The temperature increased from 23 to 45 C during the reaction. The mixture was allowed to stand overnight. To react excess isocyanate, 10 drops of additional isothiourea were added. To the reaction mixture was then added 1.83 g (0.03 mol) of 2-aminoethanol and the reaction mixture allowed to stand overnight. Methylene chloride was evaporated in vacuo and the residue treated with 25 ml of ethanol. The reaction mixture was allowed to stand for 3 days. The resulting cloudy mixture was stirred at room temperature overnight and

- 37 -

219743

then evaporated in vacuo with 13.7 g of a yellow.

3O * cloudy liquid with a refractive index η of 1.4800 would be obtained. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 64 in Table I.

Example 36

Reaction product of 2 moles of 1,3-di-N-sec-heptyl-2-S-ethylisothiourea + pp'-diphenylmethane diisocyanate. The plant described in Example 26 was used. 3.0 g (0.01 mol) of 1,3-di-sec-heptyl-2-S-ethylisothiourea were mixed with 30 ml of toluene. 1.25 g (0.005 mol) of pp ¹ diphenylmethane diisocyanate was added to the mixture and the mixture was heated to 75 to 80 ° C for 2 hours. By IR spectroscopy, a weak isocyanate peak could be observed so that 10 drops of isothiourea were added and the mixture was maintained at the indicated temperature for another 30 minutes. The reaction mixture was then stirred at room temperature overnight. The mixture was evaporated in vacuo to give 4.5 g (104% by weight of theory) of an amber liquid having a refractive index n _n of 1.5310. IR and NMR spectroscopy confirmed that it was the desired compound. Compound No. 127 in Table I.

Example 37

Reaction product of 2 moles of 1N-sec-heptyl-3-Nn-hexyl-2-S-methyl-thiomethyl isothiourea + toluene-2,4-diisocyanate. The procedure and plant of Example 36 were repeated except that as Reagent 3 , 8 g (0.01 mol) of 1-sec-Hepty1-3-Nn-hexy1-2-S-methyl-1-thiomethyl-isothiourea, 0.87 g (0.005 mol) of toluene-2,4-diisocyanate and 25 ml of tetrahydrofuran were used. After completion of the reaction, the mixture was added with 20 drops of isothiourea to react residual isocyanate at room temperature overnight. The reaction mixture

- 38 -

219743

- ³⁸ .- · "'''.,''-.'." The mixture was then evaporated in vacuo to give 4.6 g of a red-colored viscous liquid with a refractive index n_ of 1.5344. IR and NMR spectroscopy confirmed the structure of the desired product. Compound No. 138 in Table I.

Example 38

l-N-sec-heptyl-S-N-n-octyl-n-octadecylcarbamy1-2-S-alIyI-isothiourea

The plant and procedure of Example 26 were repeated. 1.9 g (0.006 Mpl) 1-sec-heptyi-3-n-octyl-2-S-allyl isothiourea was mixed with 25 ml of tetrahydrofuran and the whole was admixed with 1.77 g (0.006 mol) of n-octadecyl isocyanate , The reaction mixture was then stirred overnight at room temperature and evaporated in vacuo to give 3.79 g (100% by weight of the theoretical yield) of a clear liquid having a refractive index n_ of 1.4769. It was confirmed by IR and NMR spectroscopy that it was the desired compound Compound No. 144 in Table I.

Example 39

Reaction product of 2 moles of 1-phenyl-1-n-heptyl-S-ethyl-isothiourea + toluene-2,4-diisocyanate The plant described in Example 26 was used. 2.78 g (0.01 mol) of 1-phenyl-Sn-heptyl-S-ethyl-isothiourea in 35 ml of tetrahydrofuran were mixed with 0.87 g (0.005 mol) of toluene-2,4-diisocyanate. The reaction mixture was then refluxed for one hour on a steam bath, whereupon 15 drops of isothiourea were added and the mixture was refluxed for an additional hour to react residual isocyanate. The reaction mixture was evaporated in vacuo to give 4.1 g of a viscous yellow liquid with a refractive index η of 1.5747. IR and NMR spectroscopy confirmed that it was the desired compound. Compound No. 151 in Table I.

- 39 -

219743

Example 40

N- (5-sila-5,5-dimethyl-l-heptyl) -N'-n-heptyl-n-octadecylcarbamyl-2-S-äthylisothioharnstoff

The equipment described in Example 26 was used. 2.4 g (0.007 mol) of 1- (5'-sila-5 ', 5'-dimethyl-N-heptyl) -3-n-heptyl-2-S-ethyl-isothiourea in 25 ml of tetrahydrofuran was mixed with 2.06 g (0.007 mol) of N-octadecyl isocyanate and stirred for 2 hours at room temperature. The reaction mixture was evaporated in vacuo to give 4.51 g (100% by weight of the theoretical yield) of a clear liquid having a refractive index n_ of 1.4765. IR and NMR spectroscopy confirmed that it was the desired product. Compound No. 184 in Table I.

Example 41

N-dichloroacetyl-NyN'-di-n-heptyl-S-ethylisothiourea 3.0 g (0.01 mol) of l, 3-di-n-heptyl-2-S-ethylisothiourea were dissolved in 25 ml of methylene chloride and in a 200 ml 3-necked flask provided with magnetic stirrer. The mixture was treated with 1.1 g of triethylamine. Then, 1.5 g (0.01 mol) of dichloroacetyl chloride in 10 ml of methylene chloride was added slowly while the mixture was cooled on an ice bath. The reaction mixture was then heated to 40 C and held at this temperature for half an hour. The reaction product was washed with water, and the organic layer was dried with magnesium sulfate, filtered, and vacuum-evaporated to obtain 4.1 g of a liquid and a refractive index η of 1.4723. IR and NMR confirmed that it was the desired compound. Compound No. 332 in Table I.

Example 42 Adduct of 1 mole of 1,3-di-n-heptyl-2-S-ethyl-isothiourea

and 1 mole of diglycolic anhydride .

The equipment described in Example 41 was used.

- 40 -

219743

- 4O -, -,; · ... ^: ; '- ν-''','.^":: 3.0 g (0.01 mol), S-di-n-heptyl - ^ - S-ethyl-isothiourea dissolved in 15 ml glycol and 1.2 g (0.01 mole) diglycolic anhydride dissolved in 10 The reaction was refluxed for 10 minutes and evaporated in vacuo to give 4.1 g of liquid and a refractive index n_ of 1.4608 The product was confirmed to be the desired compound by IR and NMR spectroscopy Compound No. 321 in Table I.

Example 43 Adduct of 1 mole!, B-di-n-heptyl ^ -S-ethyl! -Isothiourea

and 1 mole of succinic anhydride

The equipment, procedure and reactants of Example 42 were used except that 1.0 g (0.01 mol) of succinic anhydride was used instead of diglycolic anhydride. The yield was 4.1 g of a semi-solid. NHR spectroscopy confirmed that it was the desired product. connection

No. 331 in Table I.

Example 44

Adduct of 1 mole of 1,3-di-n-heptyl-2-S-ethylisothiourea and 1 mole of formaldehyde ·

The equipment, method and reactants of Example 42 were used except that 1.2 grams of formaldehyde was used as a 37% solution in water (0.01 moles plus about 20% excess) rather than diglycolic anhydride. The yield was 3.3 g of a semi-solid. NMR spectroscopy confirmed that it was the desired product. Compound No. 323 in Table I. /

Example 45 Adduct of 1 mole of 1,3-di-n-heptyl-2-S-ethyl-isothiourea

and 1 mo! p-anisaldehyde

The equipment, procedure and reactants of Example 42 were used except that 1.4 g. , ' ^: ' ^: .- '-' .- 41 · -. ,

219743 \: _tl .

(O, Ol mole) Anisaldehyd instead of Diglykolsaureanhydrid were used. The yield was 4.3 g of a liquid with a refractive index ή of 1.4825. NMR spectroscopy confirmed that it was the desired product. Compound No. 328 in Table I.

- 42 -

Table 1

Connection no . 1

-C ₇ H ₁₅

S-R

RNCNR ₁ ^R 3

-C ₇ H ₁₅

-C ₂ H ₅

nf or ° C

1.4760

U) I

η average *

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ^ o

0 '''' r- \ ''

One of the reactants was Tergitol® 15-S-7, a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

^: ''. "30

Compound Nr. S ^ l ^ 2 ¹¹ D ^or

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

^C V < ^CH 2V ^CH 3 NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -O

.0 ... , ; ^; ::

η average = 11. : Ω '

One of the products in Turtji tol ~ 15-S-7 is a product of the Carbide Corporation in an average of 50,000 times where η is 9-13 and imrclisi'lini 11 is 11.

, , , , 3O

Connection no . R Κχ ^R 2 Πρ / or

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

 / ",

H ₃ CH ₃ - (CH ₂ ) _n -CH ₃

NHC-OCH ₂ CH ₂ (OCH ₂ Ch ₂ ) ₆ -0,

'; ^: ''. ' - '' - ': V ""·''. £

           "-

η average -.11 One of the reactants was Tergitol ^ 15-S-7

a product of the Union Carbide Corporation in an average molecular weight of 508 where η is 9-13 and on average 11.

Connection no

C ₇ H ₁₅

-C ₇ H ₁₅

~ ^C 7 ^H 15

" ^C 7 ^H 15

CH

η average = " ^C 2 ^H 5

^rC 2 ^H 5

Il

NCO

30 η ~ or

° C 1.5440

Thick OeI

One of the reactants was Carbowax 400, a product of Union Carbide Corporation in which the average molecular weight is 4OO and η is an average of 7.7.

Connection no.

⁰ C

_Λ or

10

12

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -C ₇ H ₁₅ -C ₇ H ₁₅ - ^C 2 ^H 5 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₃ H ₇ -C ₇ H ₁ C -C ₇ H ₁₅ -C ₂ H ₅

^C1

CH,

CH,

CH,

1.5283

1.5254

1.5235

1.5215 limit

1.5186

1.5188

1.5186

V:

Connection no.

13

" ^C 7 ^H 15

Ri

-C ₇ H ₁₅

-C ₄ H ₉

30

n ~ oaer

⁰ C

1.5180

14

15

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₅ H _n

• ^C 6 ^H 13

1.5145

1.5115 <*>

16

-C ₇ H

7 ⁿ 15

-C ₇ H ₁₅

-C ₁ H ₃

1.5250

17

-C ₇ H ₁₅

" ^C 7 ^H 15

-IC ₄ H ₉

1.5147

18

-C ₉ H ₁₉

-C ₈ H ₁₇

-C ₂ H ₅

1.5093

19

" ^C 6 ^H 13

'15

-C ₂ H ₅

1.5214

connection

No.

20

21

22

-C ₈ H ₁₇ -C ₈ H ₁₇

-C ₇ H ₁₅ " ^C 9 ^H 19

-C ₈ H ₁₇

R ₂

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

1.5175

1.5170 ^ ₀

1.5134

23

-C ₇ H ₁₅

" ^C 8 ^H 17

-C ₂ H ₅

1.5185

• Yes. 00 I

24

^C 6 ^H 13

-C ₁₀ H ₂₁

-C ₂ H ₅

1.5191

25

-C ₈ H ₁₇

- ^C 8 ^H 17

C ₄ H ₉

1.5135

26

-C ₈ H ₁₇

" ^C 8 ^H 17

C ₅ H ₁₁

1.5125

219743

ο ό

en Oo C

ο O vO O O CM m OO O OO r. f » OO f-l

"η

r cn

O-O

O = O I

CV

vO O

O = O

J ¹

ν

"O

O ι

CM O'N

"η

CM

³ CM

υ ι

σ * SC X S3 X ο ι I O O O 0-.

cn

cn

³ Co ο

O ι

CM

co

CM

CM

cn

CM

cn

Connection no.

R ₂

χξ ^Ο or

-C ₇ H ₁₅

.C ₇ H ₁₅

-C ₂ H ₅

1.4970

33

^CH 3 CH ₃ - (CH ₂ ) _n -CH ₃

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -O

η average - 11, _the reaction agent was Tergitol 15-S-7

_{The Onion} Carbide Corporation _hails "in". ^

9-13 and the average is 11.

connection

No.

34

35

36

-C ₇ H ₁₅ " ^C 7 ^H 15

" ^C 8 ^H 17

" ^C 7 ^H 15

" ^C 8 ^H 17

-C ₇ H ₁₅

- ^C 2 ^H 5

-C ₂ H ₅

-C ₂ H ₅

-CNH

^C1

O • CNH

30

or

1.5084

1.5245

1.4966

37

C ₇ H ₁₅

" ^C 7 ^H 15

- ^C 2 ^H 5

• CNH ^ ^v

Cl

1.5392

38

^C 8 ^H 17

" ^C 6 ^H 13

-C ₂ H ₅

1.5274

39

40

^C 6 ^H 13

C ₇ H ₁₅

" ^C 6 ^H 13

-C ₇ H ₁₅

" ^C 2 ^H 5

-C ₂ H ₅

• CNH

-CNHC /

Cl

1.5317

1.4750

connection

No.

" ^C 7 ^H 15

-C ₇ H ₁₅

" ^C 8 ^H 17

" ^C 6 ^H 13

" ^C 8 ^H 17

" ^C 7 ^H 15

" ^C 7 ^H 15

-C 7 ^H 15 -C 7 ^H 15 -C 6 ^H 13 -C 6 ^H 13 -C 8 ^H 17 -C 7 ^H 15 -C 7 ^H 15

-C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5

Ί ?

-CNHCH ₂ COC ₂ H ₅

-CNH - // ^χ>

CNH- / ⁷

0 CNHCH ₂ COC ₄ H ₉

η-, or

1.4800

1.5215 limit

1.5200

• 1.5261

-CNH ^ ^x V0CHo 1.5175

1.4770

1.5340

connection

No

48 49 50 51 52 53

-C ₇ H ₁₅

54

" ^C 7 ^H 15

-C ₇ H ₁₅

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

" ^C 8 ^H 17

" ^C 8 ^H 17

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5

Cl

OCH

-CNHC ₂ H ₅

η * ⁰ C

or

-CNHCH ₂ CH ₂ Cl 1.4930

1.5230

1.5190

1.5235

1.4830

-CNHCH ₂ CH-CH ₂ 1.4871

1.5270

connection

No.

55 56 57 58 59

S 61

- ^C 7 ^H 15

C ₇ H ₁₅

R-.

" ^C 7 ^H 15

-C ₇ H ₁₅

" ^C 8 ^H 17

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

R

-C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5

! 3 O -CNHC ₃ H ₇ -I

-CNH,

-jw '

or

-CNH

-CNH,

Cl

1.4765

1.4768 - *

1.5175

1.5182

1.5190

1.5310

1.4765

connection

No. 62

" ^C 7 ^H 15

C ₂ H ₅

Il

1.5237

-C ₇ H ₁₅

" ^C 7 ^H 15

" ^C 7 ^H 15

^C 2 ^H 5

C ₂ H ₅

br

1-5242 ^

Il

-CNHCH ₂ CNHCH ₂ CH ₂ Oh 1.4800

I / CNH,

1.4725

cn

C ₂ H ₅

OCHO 1-5210

67

"SeJcC ₇ H ₁₅

" ^C 6 ^H 13

C ₂ H ₅

soft solid

68

" ^C 6 ^H 13

C ₂ H ₅

1.5230

connection

No.

69 70 71 72

73 74 75 76

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -sekC ₇ H ₁₅ " ^C 6 ^H 13 -sekC ₇ H ₁₅ -sekC ₇ l

R ₂

" ^SekC 7 ^H l5" ^C 2 ^H 5

-C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5

q

-CNHC ₁₂ H ₂₅

-CNHC ₁₈ H ₃₇

O -CNHC ₁₀ H ₃₇

30 ⁰ C

or

1.5125 1.5115 1.5205

1.4720

1.5390 1.4765

1.4737 1.4750

connection

  No.

77

80 81

tC ₈ H ₁₇ -C ₈ H ₁₇ sekC ₇ H ₁₅ " ^C 8 ^H 17 sekC ₇ H ₁₅ -C ₈ H ₁₇ sekC ₇ H ₁₅ -C ₈ H ₁₇ sekC ₇ H ₁₅ -sekC ₇

R ₂

-c ^2H 5 -C 1 ^H 3 -C 1 ^H 3 -C 1 ^H 3

/ ι

-cnik / ^x ;

• 2 ⁿ 5

nj? or C ⁰

-CNHC ₁₈ H ₃₇ 1.4755

1.5280

-CNHC ₁₈ H ₃₇ 1.4750

-CNH-Z ⁷ VCl · 1.5335

1.5305

-s eke

-C ₂ H ₅

O, Cl

1.5240

SEC ₇ H

-C ₂ H ₅

-CNHC ₁₈ H ₃₇

1.4740

Connection no. R H. 84 -sekC ₇ H ₁₅ - ^C 8 ^H 17 85 2-ethylhexyl 2-ethylhexyl

.30

85 - nj ^w _o the C - 1.5201

86 87 88

" ^C 8 ^H 17

-C ₈ H ₁₇

-C ₂ H ₅

-C ₂ H ₅

" ^C 1 ^H 3

³⁰ or C

δ> ci

CNH ^ V-Cl

1.5295

CNH

CH,

= 7 0 2-ethylhexyl

: C-NC »N-2-ethylhexyl SC ₂ H ₅

-CNHC ₁₈ H ₃₇ -n 1.4740

1.5342

1.5276

-CNH-

89

• ^tC 8 ^H 17 ⁹ - ^C 8 ^H 17

-C ₁ H ₃

-CNH-C ₁₈ H ₃₇

1.4772

Connection no.

90

" ^C 8 ^H 17

-C ₂ H ₅

_n 3 ° or ⁰ C

1.5324

91

" ^C 8 ^H 17

-C ₂ H ₅

N-SeJtC ₇ H ₁₅ ^C 8 ^H 17

- i ^ ° or ° C - 1.5170

σι O ι

92

93

94

95

-sekC ₇ H ₁₅ -sekc ₇ H ₁₅ -C ₁ H ₃ O Il -CNH ICl / I! / Cl O ^ Cl -0-C1  2-ethylhexyl -2-ethyl-hexyl -C ₂ H ₅ 0 -CNH-C ₁₈ -H ₃₇ 2-ethylhexyl 2-ethylhexyl -C ₂ H ₅ 0 -CNH 2-ethylhexyl -2-ethylhexyl -C ₂ H ₅

1.5292

1.5258

1.4760

1.5306

CNVO

Connection no. R H 96 2-ethylhexyl 2-ethylhexyl 97 -2- ethyl hexyl -C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

⁰ C

or

'' AV-OCH,

1.5238

1.5145 SC ₂ H,

N-2-ethylhexyl

CN-C-SC ₂ H ₅

C ₇ H ₁₅

98

-C ₂ H ₅

1.5120

NHCN-C-SC ₉ H

99

• 2-ethylhexyl

-2-ethylhexyl

-C ₂ H ₅

1.5330

Connection no.

100

-tC ₈ H ₁₇

" ^C 8 ^H 17

-C ₁ H ₃

⁰ C

or

OCHo 1.5020

101

102

 2-Aethylhexvl

-C ₂ H ₅

-C ₂ H ₅

1.5000 ^

CH

NHCN-C-SC ₂ H ₅

Il ο

C ₇ H ₁₅

102 - nj * ⁰ Qdex ^e C - 1.5226

103

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

1.5275

CH ₃

connection

No.

104

  2-Aethy1-

hexyl

-C ₇ H ₁₅

-C ₃ H ₇

nj> ° or ⁰ C

NHCN-C-SCoH ₇

¹ Il

N-2-ethylhexane

C ₇ H ₁₅

104 -n? ⁰ or «c - 1.5190

105

" ^tC 8 ^H 17

-2-ethylhexyl

-C ₂ H ₅

CH,

NHCN-C-SC ₉ Hc

NC ₈ H ₁₇ -t

2-ethylhexyl

105 - .ni * ° ^or ° C - 1.5182

106

-2-ethylhexyl

-C ₇ H ₁₅

-C ₂ H ₅

Cl

1.5277

Connection no.

107 108 109 110 111 112 113

2-ethylhexyl -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₈ H ₁₇ 2-ethylhexyl " ^C 7 ^H 15 2-ethylhexyl -C ₇ H ₁₅ • 2-ethylhexyl -C ₇ H ₁₅ 2-ethylhexyl -C ₇ H ₁₅ -sekC ₇ H ₁₅ " ^C 7 ^H 15

or

-C ₂ H ₅ O -CNHC ₁₈ H ₃₇ -CH ₂ SCH ₃ O -C ₃ H ₇ O -C ₃ H ₇ O _xCl -C ₃ H ₇ O Ii -CNHC-t 0Hn ₇ 0 _ / Cl -C ₃ H ₇ -CNlH ^ -C ₃ H ₇ 0 Il -CNHC · »qHo» »

1.4775

1.5255 - *

1.5200

1.5337 S-. r

1.4772

1.5237

1.4744

connection

No .

114

-2-ethylhexyl

" ^C 8 ^H 17

22 -C ₂ H ₅

nj: or ⁰ C

NHCN-C-SC ₉ Hc

Il ^{2 5}

NC ₈ H ₁₇

2-Aethv] hexvl

114 -n ^ ° or ^e C - 1.5170 115

" ^C 6 ^H 13

C ₂ H ₅

'VcHöV V-NHCN-C-SC-ft.

^C 6 ^H 13

.30

115 - t ^ ^u or ° C - 1.5350 116

" ^C 6 ^H 13

116 - nj * ⁰ or ° C - 1.5220

C ₂ H ₅

-sekCyHjc

Connection no.

117

- ° 6 ^Η 13

117 - n ° J or ° C - 1.5234 118

-C ₇ H ₁₅

2-ethylhexyl. Hexyl

" ^C 8 ^H 17

-C ₂ H ₅

C ₁ H ₃

.30

or

NHCN-C-SC ₂ H ₅

2-ethylhexyl®

NC ₆ H ₁₃

^ HaN-C-

NC ₇ H ₁₅

^C 8 ^H 17

OV

cn ι

118 - n2 ° or ° C - 1.5190 119

-2-ethylhexyl

" ^G 8 ^H 17

C ₂ H ₅

-CNHC ₁₈ H ₃₇

1.4765

Connection no.

120

121

" ^tC 8 ^H 17

-tC ₈ H ₁₇

 2-ethyl

hexyl

" ^C 8 ^H 17

-C ₃ H ₇

C ₃ H ₇

-CNH

or

CH.

1.5120

NHCN-C-SC ^ H ₇

2-ethylhexyl

1.5124

NHCN-C-SC ₃ H ₇

NC ₈ H ₁₇ -t ^C 8 ^H 17

σι σ \ ι

σιοο οι

122

123

 2-ethyl ·

hexyl

 2-ethylhexyl

" ^C 8 ^H 17

" ^C 6 ^H 13

.C ₂ H ₅

.C ₂ H ₅

1.5264

1.5296

connection R ^R l No. .- "f. -2-ethylhexyl j. " ^C 6 ^H 13 124 -C ₇ H ₁₅ % 2-ethylhexyl 125

on 125 ng or ° C - 1.5393 C ₂ H ₅ C ₂ H ₅

or

-CNHC ₁₈ H ₃₇ 1.4770

ICNC = NC ₇ H ₁ c, 7

2-Aethvlhexyl

126

127

.30

127 - year ^U or ° C - 1.5310

128

-2-ethylhexyl

128 - nT or ° C - 1.5340

" ^C 8 ^H 17

2-ethylhexyl

II

-C ₂ H ₅ -CNHC ₁₂ H ₂₅ 1.4763

II

SC ₂ H ₅

-3ek-

[N-2-ethylhexyl 2-ethylhexyl

connection

/No.·"

129

^C 8 ^H 17

2-ethylhexyl. Hexyl

_n 30 or

⁰ C 0

ti

[CNC SC ₀ H ,.

Il * - J

NC ₈ H ₁₇

2-ethylhexyl

129 - ny * or ° C - 1.5300

130 131 132 133

CTi VO

-2-ethyl "

hexyl

-2-ethylhexyl

2-ethylhexyl. Hexyl

" ^C 6 ^H 13

-C ^2H 5 -C ^2H 5 -C ^3H 7 -C ^2H 5

Cl

Cl

1.5271

1.4785 p

1.5150

? I

CNC = NC ₇ H ₁ «-" sec.

I ^{7 15}

^C 6 ^H 13

133 -

- 1.5345

Verbindunq

No.

134

-sek ^cC 7 ^H 15

134 - n ° or ° C - 1.5283 135

-sekC ₇ H-,

-2-ethyl ·

hexyl

-2-ethylhexyl

-C ₂ H ₅

-C ₂ H ₅

or

SC ₀ Hc / ι 2 5

C-NC

NC ₇ H ₁₅ -SeIc

2-ethylhexyl ·

NHCN-C-SC ₀ Hc iff 25 I NC ₇ H ₁₅ -SeIc

2-ethylhexyl

135 - n ° or ° C - 1.5164 136

-2-ethylhexyl

-C ₃ H ₇

NHCN-C-SC ₃ H ₇

NC ₇ H ₁₅ -SeIc

CH,

- * 2-ethylhexyl

cn

.30

136 - ny or ° C - 1.5165

<? 137

-2-ethylhexyl

.C ₃ H ₇

0 .CNHC ₁₈ H ₃₇

1.4745

Connection no.

138

.30

138 - nJ ^U or ° C - 1.5344

139 140

-SeJcC ₇ H ₁

-2-ethyl

hexyl

t <y

-CH ₂ SCH ₃

-C ₂ H ₅

"30

⁰ C SCH ₉ SCH ^

or

HHCNC-NC ₇ H ₁₅ -sec '" ^{SV έ} 6 ^Η 13

CHQ

-CNHC ₁₈ H ₃₇

1.4750 SCHo

^C 8 ^H 17

- sec

140 - nj * ° or ^B C - 1.5293

141 142

• 2-ethylhexyl

-2-ethylhexyl

-C ₂ H ₅

.C ₃ H ₇

Cl

Cl Cl

1.5295

1.5317

connection

No.

143

Cl Uf

CH.

-C ₂ H ₅

Cl

or

1.5758

144

145

-sekC-, Η

" ^C 8 ^H 17

-CH ₂ CH-CH ₂

-CH ₂ CH-CH ₂

-CNHC _1ft H, ₇ 1.4769 ^{10 w} ' _o SCH ₂ CH = CH ₂

NHCNC = NC ₇ H ₁ ς-sec

U ⁷

145 - n ° or ° C - 1.5225 146

-C ₇ H ₁₅

-CNHC ₁₈ H ₃₇

1.5140

147

-2-Aethylhexvl

147 - np ° ^or> C - 1.5290

-C ₇ H ₁₅

-NHCNC-SC-H ₇

H ^J 'N-2-ethyl

hexyl C ₇ H ₁₅

connection

No. 148

-C ₇ H ₁₅

" ^C 8 ^H 17

CH ₂ CH = CH ₂

τξ ° or

° c

NHCN-C-SCH ₉ CH-CH

^C 8 ^H 17

148 - ny * ° or. ^e C - 1.57357

149

-C ₇ H

7 ⁿ 15

-C ₂ H ₅

Cl

Cl

1.5785

150

-sek C ₇ H ₁₅

151

• ^C 8 ^H 17

-C ₇ H ₁₅

-CH ₂ CH-CH ₂

Cl

Il ϊί. , NHCNC

^{/ 7} V 1 '

^CH 3

1.5326

to

OHC

^C 7 ^H 15

^ 151 - ny * ° or ° C - 1.5737

2197

νθ O r-4 O SO r » CM O m m

vO

vO r-l

O = 'O =

p · "

 €

O = O ι

O = O

CNI

r ". m to m X X 32 33 X s cn CN CN CN O O O O O I I I I I

³ Sun

(U

0} I

• H S ^

Xl Z

CM

in

m m m ⁰ OO OI SS υ ³ COI P · »I m -j I X

cn __ | O m O) • cfl I I O O U Q) ti O O cn ^ p I CN cn m m

P ^

Φ co ι

m m

-74-

connection

No.

⁰ C

or

158

158 - n {J ^0odero C - 1.5860 159

" ^C 8 ^H 17

C ₇ H ₁₅

C ₂ H ₅

(CH _{2) 6} -C ₂ H ₅ C1

O »Cjjir - // \ N

-CNHC ₁₈ H ₃₇

0 SC ₂ H ₅

NC = N /

C ₇ H ₁₅

1.4876

160

-C ₇ H ₁₅ -C ₂ H ₅

CNH ( ⁷ V OCH

1.5743

161

" ^C 7 ^H 15

-C ₂ H ₅

0? ^C 2 ^H 5

C ₇ H ₁₅

161 - n ° or ° C - 1.5760

ⁿ D

162

" ^C 12 ^H 25

-C ₂ H ₅

-CNHC ₁₈ H ₃₇

1.4736

connection R ^R l R ₂ .No. -C ₈ H ₁₇ JL (CH ₂ ) ^ C ₅ H ₁₁ i. - ^C 2 ^H 5 163 -sekc ₇ H ₁₅ 2-ethylhexyl -IC ₄ H ₉ 164

165 166 167 168

169

" ^C 7 ^H 15 Chae-CvwCHa- -C ₂ H ₅ " ^C 7 ^H 15 (CH ₂ ) ₃ OCH ₃ - -C ₂ H ₅ -2-ethyl-hexyl. O (CH -C ₃ H ₇ 2V -C ₂ H ₅ " ^C 8 ^H 17 O (CH ₂ ) ₆ OCNHCH ₃ - -C ₂ H ₅ -sekC ₇ H ₁₅ 2-ethylhexyl -IC ₃ H ₇

"CtNHCi o

O -CNHC ₁₈ H ₃₇

O -CNHC ₁₈ H ₃₇

nf or ⁰ C

-CNHC ₁₈ H ₃₇ 1.4850

1.4754 ^ 1.4810 4 *

• 1.4773

-CNHC ₁₈ H ₃₇ 1.4746

1.5244

-CNHC ₁₈ H ₃₇ 1.4738

connection

No_.

or

-2- ethyl hexyl 2-ethylhexyl -C ₂ H ₅ -sekC ₇ H ₁₅ -C ₉ H ₁₉ -C ₇ H ₁₅ -sekGyH- ^ c -C ₇ H ₁₅ -C ₂ H ₅ > ^CH 2- CH ₂ - ^) -C ₂ H ₅ -sekCyHj ^ (CH ₂ ) ₃ C1- - ^C 2 ^H 5 2-ethylhexyl (CH ₂ ), OCH, - -C ₂ H ₅ -C ₇ H ₁₅ -C ₅ H ₁₁

Il CNHC

-t o

CNHC ₁₈ H ₃₇

O CNHC ₁₈ H ₃₇

O CNHC ₁₈ H ₃₇

-CNHC ₁₈ H ₃₇ 1.4836

1.4735

1.4740

, 1.4845

1.4930

1.4950

-CNHC ₁₈ H ₃₇ 1.4755

Connection no.

177

-C ₇ H ₁₅

" ^C 5 ^H 11

Il

-CNHC ₁₈ H ₃₇

τι or ⁰ C

1.4750

178

αΑΑΛ

-C ₇ H ₁₅

-C ₂ H ₅

-CNHC ₁₈ H ₃₇

1.4760

179

- SΘΚC ^ H-I e "Ci λΗλε

-C ₂ H ₅

0 SC ₉ H NHCN-C

^C 12 ^H 25

179 - nj * ° or ^e c - 1.5215

180

2-ethylhexyl O? ^C 2 ^H 5

NHCN-C I

NC ₇ H ₁₅ : sec

2-ethylhexyl

180 - n ° or ° C - 1.5295

Connection no.

181

" ^C 8 ^H 17

II

(CH _{2) 6} H ₂ OCNHC

'2 ⁿ 5

(I

C!

30, η or

⁰ C

1.5205

182

183

" ^C 12 ^H 25 ~ ^C 2 ^H 5

" ^C 7 ^H

7 ^H 15

-C ₂ H ₅

Il

 CNH

Il

• CNH

Cl

Cl

1.5070 \ ^

1.5825

184

CH ₃

C ₂ H ₅ Si (CH ₂ ) ₄ CHo

-C ₇ H ₁₅

-C ₂ H ₅

-CNHC ₁₈ H ₃₇

1.4765

185

H-

ic

-C ₂ H ₅

SCOH

Il

NHCN-C

2 ⁿ 5

CH,

NCH

C ₇ H ₁₅

1.5770

connection

No.

186

" ^C 8 ^H 17

-C ₂ H ₅

30 _Λ n_ or

⁰ C

1.4890

187

188

2-ethylhexyl

-C ₇ H ₁₅

 2-ethylhexyl

- (CH ₂ )

CH ₂ CH-CH ₂

-CNHC ₁₈ H ₃₇

0 -CNHC ₁₈ H ₃₇

1.4800

1.4780

189

  2-Aethy1-

hexyl

-2-ethylhexyl

-C ₃ H ₇

Ο -CNHC ₁₈ H ₃₇

• 1.4757 S

190

" ^C 8 ^H 17

-CNHC

-i q

1.4924

191

2-ethylhexyl

1.5210

192

" ^C 8 ^H 17

2 ^ 5

Cl

1.5386

Connection no.

193

-C ₇ H ₁₅

CH ₂ CH-CH ₂

194 2-ethylhexyl-O- (CHj) ₃ - -C ₃ H ₇ 195

196

2-ethylhexyl

2-Aet

hexyl

-O

-C ₂ H ₅

-IC ₃ H ₇

-C ₂ H ₅

or

1.5450

1.5250

1.5195

1.5395 ο

197

r2-ethylhexyl

-C ₇ H ₁₅

1.5146

198

-SeJcC ₇ H ₁₅

-CH ₂ -

2 "V

-CNHC ₁₈ H ₃₇ 1.4820

199

-C ₇ H ₁₅

.C ₇ H ₁₅

AUUVjA [Ip

1440

Connection no.

200

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₂ H ₅

O-CH ₂ CH ₂ CCH ₃

or

1.4543

201

202

203

204

205

206

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₇ H ₁₅

^C 7 «15

-C ₇ H ₁₅

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

-C ₇ H ₁₅

C ₇ H ₁₅

C ₇ H ₁₅

^C 7 ^H 15

-C ₂ H ₅

-C ₂ H ₅

-C ^2H 5 -C ^2H 5 -C ^2H 5 -C ^2H 5

-S-CHo ti 3 Ο

-SC ₀ Hc • ι *>

-sV / χ>

1.4807

1.4836

1.4805

1.4902

1.5152

_ ^N > -CH ~ 1.517

Connection no.

207 208 209

" ^C 7 ^H 15

" ^C 7 ^H 15

-C ₇ H

15

" ^C 2 ^H 5

-C ₂ H ₅

-C ₂ H ₅

5?

/ ι X 0

or

1.5207

1.5215 limit

1.5273

Connection no.

210

211

212

213

CF

Cl

Cl

egg-//

CF

-C ₁ H ₃

-C ₁ H ₃

-C ₁ H ₃

-C ₁ H ₃

R '

-CH ₂ COCH ₃ -CH.

0 -CH ₂ COCH ₃ -CH,

0 -CH ₂ COCH ₃ -CH,

0 -CH ₂ COCH ₃ -CH,

n_ or ⁰ C

1.5308

1.5559 -

Dark OeI

1548

214

-C ₁ H ₃

-CH ₂ COCH ₃ -CH,

Dark OeI

215

OO id 1

SCF.

-C ₁ H ₃

-CH ₂ COCH (CH ₃ ).

1.5417

30

Compound J * ^R l ^R 2 ⁿ D ^or

No. . ° ^c

-C ^ H _1c -C ₇ H ,,: -C ₉ Hc 1.5785

* ^C 7 ^H 15. -C ₇ H ₁₅ H -In-Q- : H ₂ (OCH ₂ CH ₂ ) _n OCH ₃ -CH ₃ Si NHC-OCH ₀ C κ * 0

η average = 6.2 ^)

Hines of the reactants was Carbowax 350

Product of the Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2 on average.

Connection no

_n ³⁰ or

on

217

-C ₆ H ₁₃ -C ₆ H ₁₃

-C ₂ H ₅

1.5838

217

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

η average -6.2 _{pounds of the reactants was C} arbowax® 350

Product of the Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2.

Connection no .

° c

218 218

-C ₆ H ₁₃

-C ₈ H ₁₇

CH ₃

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

η average = 6.2 C ₂ H ₅

1.5800

In terms of the reactants, Carbowax 350 was a product of Union Carbide Corporation in which the average molecular weight was 350 and η was 6.2 on average.

t

Compound No. RR ^ ^ 2 ¹¹ D

" ^C 7 ^H 15" ^C 7 ^H 15 ~ ^C 2 ^H 5 1.5710

-CNH- ^ 3 CH- (CH ₂ ) ^

NHC-OCH ₂ CH ₂ (OCH ₂ Ch ₂ ) ₆ -O 0

η average = 11 *. _Λ ι® τ c_c-7

One of the reactants was Tergitol 15-S-7

a product of Union Carbide Corporation in one

a p

Average molecular weight of 508 where η is equal to

9-13 and the average is 11.

CJ

.00 -4

Connection Nr,

"30 ¹¹ D

⁰ C

or

220

" ^C 8 ^H 17

-C ₂ H ₅

1.5700

220

CH ₃ - (CH ₂ ) _n -CH ₃

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ »

η average = 11 One of the reactants was Tergitol ^ 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no.

or

221

" ^C 8 ^H 17

" ^C 6 ^H 13

-C ₂ H ₅

1.5680

221

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) g-0

η average =

Wed.

One of the reaction thresholds was Teryitol ^^ 15-S-7, a product of the Unit Carbide Corporation in a cross-link molecular weight of 508 where η is equal to 9-13 and averages 11.

Connection no.

222

222

-C ₆ H ₁₃

C ₆ H ₁₃

-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -0

-C ₂ H ₅

1.5720

η average = 11 One of the reaction products was Tergitol 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no.

ny ° or

223

" ^C 6 ^H 13" ^C 8 ^H 17

-C ₂ H ₅

1.5746

223

I ' NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) g-0

η Average = One of the Heak L i onsiui ttol was Tery i tol ^VC! 15-S-7 is a product of Union Carbide Corporation in a Durehsehni ttsntol ekulanjewi of 508 where η is 9-13 and in Durehsehnitt U.

30

\ R ^ rhindunq Nr._ RR ₁ R ₂ % ^or

- - ° c

-C ₈ H ₁₇ -C ₈ H ₁₇ -C ₂ H ₅ 1.5726

R ₃

224 -CNH- ^ V-CH

3 CH ₃ - (CH ₂ ) _n -CH ₃

NHC-OCH ₂ CH ₂ (OCh ₂ CH ₂ ) ^ - O - £

δ '

η average = 1 _{One of the} reactants was Tergitol® 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no. R " ^C 6 ^H 13 ^ 2 R ₃ 225 " ^C 6 ^H 13 -C ₂ H ₅ O 225 · - 1.4930 O Il If) • nj or ⁰ C

226

-C ₇ H ₁₅

226 - n ° or ° C - 1.4895

227

" ^C 8 ^H 17

" ^C 8 ^H 17

-C ₂ H ₅

-C ₂ H ₅

(OCH ₂ CH ₂ )

Il

227 -

228

- 1.4885

" ^C 8 ^H 17

" ^C 6 ^H 13

-C ₂ H ₅

-CNH 3 3- (OCH ₂ CH ₂ ) ₂ OC ₂ H ₅

228 - n ** ⁰ or ^e C - 1.4892 229

-C ₇ H ₁₅

~ ^σ 7 ^Η 15

-C ₂ H ₅

0 -P (OCH ₃ )

1.4528

230

-tC ₈ H ₁₇

° 8 ^H 17

-C ₂ H ₅

-P (OC ₃ H ₇ ) ₂ 1.5460

Connection No. 231

-C ₈ H ₁₇

-C ₂ H ₅

30 or

-P (NH ₂ ) ₂

D ⁰ C

1.4552

232

-C ₂ H ₅

-L / T ^C1

1.5035

233

• tC ₈ H ₁₇

" ^C 8 ^H 17

-C ₂ H ₅

CH ₃ 1.4913

234

" ^C 8 ^H 17

-C ₂ H ₅

Cl

1.4950

235

' ^tC 8 ^H 17

" ^C 8 ^H 17

-C ₂ H ₅

CH

1.4863

236

-WJ ₈ H ₁₇

~ ^C 8 ^H 17

-C ₂ H ₅

.OCH.

1.5010

«237

• tC ₈ H ₁₇

" ^C 8 ^H 17

-C ₂ H ₅

1.5020

Connection no.

238

238 -n ° or ° C - 1.5018 239

240

-tC ₈ H ₁₇

" ^tC 8 ^H 17

-C ₇ H ₁₅

" ^C 6 ^H 13

" ^C 6 ^H 13

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

ng ^ü or ⁰ C

CH

-n-c-sc-h,

II- ^l

Cl

Il

NC ₇ H ₁₅

C ₇ H ₁₅

1.5082

-CNH - (^) - OCH ₃ 1.5063

241

tC ₈ H ₁₇

-C ₇ H ₁₅

-C ₂ H ₅

242

" ^C 7 ^H 15

-C ₂ H ₅

ii

-Cl

Raw solid

243

-C ₇ H ₁₅

-C ₂ H ₅

Il

1.5033

244

" ^C 7 ^H 15

-C ₂ H ₅

CN

Cl

1.5044

Connection no.

245

-tC ₈ H ₁₇

' ^C 2 ^H 5

n ³⁰ or ⁰ C

^ CH.

-CNR / '*

1.4985

246

247

^{> tC} 8 ^H 17

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

³ 1.4990

248

• ^tC 8 ^H 17

-C ₇ H

7 ⁿ 15

-C ₂ H ₅

NO ₉ W ²

1.4942

249

• ^tC 8 ^H 17

-C ₄ H ₉

-C ₂ H ₅

1.5140

250

-tC ₈ H ₁₇

-C ₄ H ₉

-C ₂ H ₅

1.5135

251

" ^C 7 ^H 15

-C ₂ H ₅

-CNH - (^)

1.4673

connection

No.

252

-tC ₈ H ₁₇

C ₂ H ₅

nj * ° or ⁰ C

1.5060

253

-tC ₈ H ₁₇

C ₂ H ₅

1.5052

254

• ^tC 8 ^H 17

-C ₄ H ₉

C ₂ H ₅

f _e ^h _{s substance}

255

-tC ₈ H ₁₇

-C ₄ H ₉

C ₂ H ₅

U4953

256

• ^tC 8 ^H 17

-C ₄ H ₉

IC ₄ H ₉

JqJ / n \ _ ei 1.4953

257

tC ₈ H ₁₇

-C ₄ H ₉

1.5078

258

• ^tC 8 ^H 17

-C ₄ H ₉

iC ₃ H ₇

1.5048

connection

No. 259

-WJ ₈ H ₁₇

-C ₄ H ₉

-ic ₃ H ₇

.30

or

1.5120

260

261

^C 7 ^H 15

-C ₇ H

₇ H ₁₅

C ₁ H ₃

C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

1.52A0

OS -CCH ₂ SP (OC ₂ H ₅ ) 2 1-5060

262

C ₇ H ₁₅

C ₇ H ₁₅

-C ₂ H ₅

OS CCH ₂ SP (OCH ₃ ) ₂ 1.5100

30

Compound No. R ^R l ^R 2 ° D

-C ₇ H ₁₅ -C ₇ H ₁₅ . -C ₂ H ₅ 1.5030

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

_m C. O ®

^{n Durc f} · · ^Δ One of the reactants was Carbowax 350

Product of the Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2 on average.

Connection No. RR * R_ f £?

nj * ° or ⁰ C

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

S / Λ

²⁶⁴ -CNH- ^ V) CH ₃ - (CH ₂ ) _n -CH ₃

CH ₃ TIHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -0

η average = 11 One of the reagents was Tergitol® 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

O J

Compound No. RR ₁ ^R 2 ^ ^or

²⁶⁵ " ^C 8 ^H 17" ^C 8 ^H X7 " ^C 2 ^H 5 1.4942,"

R ₃

265 CNHHf ^ CHo (

NHC OCH ₉ CH ₀ (OCH ₀ CH ₉₎ ^ - OO

η average = 11 One of the reactants was Tergitor ^ 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Compound No. R. R ₁ R ₂ ηΤ ° or

"C ₆ Hl ₃ -C ₆ H ₁₃ -C ₂ H ₅ 1.4955

R ₃

-CNH - (/ ΛCH ^ - (CH ₉ ) "- CHo

CH ₃ NHC-OCh ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -O

ο Λ

  ·. s

η average = 11 One of the reagents was Tergitol® 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

30 R ₁ R ₂ η _β ^υ or

mi ^ m " mm Ολ

" ^c 6 ^H l3" ^C 8 ^H 17 " ^C 2 ^H 5 1.5025

R ₃

^J

-CNH - //

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n CX: H3, L

W

Average = 6.2 One of the reagents was Carbowax 350

Product of the Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2 on average.

Connection no . R. R ₁ R _{2 nβ} or

⁰ C

" ^C 8 ^H 17" ^C 8 ^H 17 " ^C 2 ^H 5 1.5005

R ₃

NHC-OCH,

M

η average = 6.2 ^ of the heaters was Carbowax 350 a

Product of Union Carbide Corporation in which the average molecular weight is 350 and n is 6.2 on average.

Connection no.

_n 30

269

" ^C 6 ^H 13

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

1.5065

269

CHr

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

η average = 6.2 · (R)

() One of the reactants was Carbowax 350, a product of Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2 on average.

Connection no.

270

" ^C 6 ^H 13

" ^C 2 ^H 5

CH,

n _ß or ⁰ C

Soft wax

271

272

• ^C 8 ^H 17

• ^C 8 ^H 17

• ^C 8 ^H 17

' ^C 6 ^H 13

-C ₂ H ₅

-C ₂ H ₅

1.5166

CH ₃ 1.5200

273

* ^C 8 ^H 17

• ^C 6 ^H 13

-C ₂ H ₅

CH,

1.5024

274

• ^C 8 ^H 17

^C 6 ^H 13

-C ₂ H ₅

Cl

1.5240

275

• ^C 8 ^H 17

• ^C 6 ^H 13

-C ₂ H ₅

• iW '^

1.5205

276

^C 8 ^H 17

• ^C 6 ^H 13

-C ₂ H ₅

OCH,

1.5215 limit

connection

No.

in

-C ₈ H ₁₇

R ₂

-C ₇ H ₁₅ -C ₂ H ₅

or

1.5256

278

279

• ^C 8 ^H 17

• ^C 8 ^H 17

-C ₂ H ₅

-C ₂ H ₅

OCH

1.5219

V-Cl 1.5351

280

• ^C 8 ^H 17

-C ₇ H ₁₅

-C ₂ H ₅

1585

281

• ^C 8 ^H 17

-C ₇ H ₁₅

-C ₂ H ₅

1.4974

282

• ^C 8 ^H 17

^C 8 ^H 17

-C ₂ H ₅

-Cl

-OCHq

// Λ

1.5205

283

^C 8 ^H 17

^C 8 ^H 17

-C ₂ H ₅

-Cl

V CI 1.5246

connection

284

285

286

" ^C 8 ^H 17

-C ₈ H ₁₇

" ^C 8 ^H 17

R-.

- ^C 6 ^H 13

- ^C 6 ^H 13

-C ₇ H ₁₅

^iC 3 ^H 7

IC ₃ H ₇

C ₂ H ₅

n ° or

1.5072

Cl

Cl

1.5242

1.5228

287

" ^C 8 ^H 17

" ^C 6 ^H 13

C ₂ H ₅

-CNH- / ' ^s >

1.5244

288

- ^C 8 ^H 17

" ^C 6 ^H 13

IC ₃ H ₇

1.5286

289

" ^C 8 ^H 17

289 - n3 ° or ° C - 1.5217

-C ₇ H ₁₅

-C ₂ H ₅

"I C

SC ₉ Hc

ΝΗέ-N-C

NC ₈ H ₁₇

C ₇ H ₁₅

connection

No.

Ri

n_ or ⁰ C

290

" ^C 8 ^H 17

- ^C 6 ^H 13

-C ₂ H ₅

NO,

1.5331

291

" ^C 8 ^H 17

291 - n ^ ⁰ or ° C - 1.5201

" ^C 6 ^H 13

-IC ₃ H ₇

SCoH ₇ -I

-N-C

CH

NC ₈ H ₁₇

^C 6 ^H 13

292

-C ₈ H ₁₇

" ^C 5 ^H 11

-C ₂ H ₅

O ^

NHC-N-C

CH

NC ₈ H ₁₇

j * °

292 - ny * or ° C - 1.5258

connection

No.

293

~ ^C 8 ^H 17

-C ₈ H ₁₇

-C ₂ H ₅

Il

⁰ l

it I

NHC-N-C

η ³⁰ or ⁰ C

RTHC

CH,

NC ₈ H ₁₇

C ₈ H ₁₇

293 - n ° or ^# C - 1.5193

294

" ^C 8 ^H 17" ^C 6 ^H 13

-C ₂ H ₅

NHC-N-C

SC ₂ H ₅

CH-

NC ₈ H ₁₇ ^C 6 ^H 13

.30

294 - lower ° C - 1.5177

connection

No.

295

" ^C 6 ^H 13

" ^C 6 ^H 13

τξ ° or ⁰ C.

NHC-N-C

CH.

SCrtHc

^C 6 ^H 13

295 - nj * ⁰ or ° C - 1.5266

296

" ^C 8 ^H 17

• ^C 6 ^H 13

NHC-N-C

SC ₃ H ₇

H.

ncoh

8 ⁿ 17

^C 6 ^H 13

296,297

298 299

- 1.5182 -C ₇ H ₁₅ -C ₂ H ₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ " ^C 7 ^H 15 " ^C 7 ^H 15 -C ₂ H ₅ -C ₇ H ₁₅

1.5084

.SCCl ₂ CFCl ₂ 1.5091

-SCCl ₂ CHCl ₂ 1.5192

connection

No.

300

301

302

303

-CH

15

-2-ethylhexyl

-C ₇ H ₁₅

^C 4 ^H 9

" ^C 7 ^H 15 -C ₂ H ₅ 2-ethylhexyl -C ₂ H ₅ -C ₇ H ₁₅ -C ₂ H ₅ -C ₄ H ₉ " ^C 8 ^H 17

_n or

NO,

1.5463

-SCCl "

NO,

CH,

1.5060

1.5580

O? ^C 8 ^H 17

it I C-N-C

NC ₄ H ₉

C ₄ H ₉

303 - n2 ° or ^o C - 1.5245

304

" ^C 8 ^H 17

-3,7-dimethyl-2,6-octadienyl

-CNHC ₁₂ H ₂₅ 1.4882

305

-C ₄ H ₉

-3,7-dimethyl-2,6-octadienyl

-CNHC ₁₈ H ₃₇

1.4848

connection

.No.

306

306 307

307 308

-C ₁ H ₃

-C ₂ H ₅

- 1.5091

-2-ethylhexyl

R ₁

-2-ethylhexyl

τξ ° or ⁰ C

ι

I

NHC-N-C

NCH

CH.

-CNH-fi ^ V-NHC-N-C

urto

NC ₂ H ₅

NHC-N-C

CH.

N-2-ethylhexyl 2-ethylhexyl

.30

308 - n ^ ^v _or ° C - 1.5029

Connection no.

309

-2-ethylhexyl

.30

309 - nj "or ° C - 1.5253

310

310 -

-2-ethylhexyl

30

or ° C - 1.4600

-2-ethylhexyl

-SCH ₂ CH ₂

2-ethyl-SHACH «hexyl *

^CH

ny * or ⁰ C

0? ^CH 2 ^CH 2

-N-C

N-2-ethylhexyl

2-ethylhexyl

CH

CH,

f «

N-2-ethylhexyl

2-Aethvlhexyl

311 "30 o _c D or -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ 312 " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 313 - ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ , 313 - Low melting material

-CCH ₂ CCH ^ O

-CCH ₂ Cl 00

-CCNH (CH ₂ ) 3N (CH ₃ )

Connection no.

314

-C ₇ H ₁₅ " ^C 7 ^H 15" ^C 2 ^H 5 "30 n_ or

2 ° c

-CCNHCoH ₇ -I; low melting ^J '^; material

315

316

-C ₇ H ₁₅

C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

CCNHCH ₂ CH-CH ₂ low melting point

shiny material

-CCH ₂ N (C ₂ H ₅ ) 3 Cl

solid fuel

317

C ₇ H ₁₅

-C ₇ H

15

Cl® half

solid fuel

318

^C 7 ^H 15

-C ₇ H ₁₅

hygroscope

319

CH

15

" ^C 7 ^H 15

CNH <w)

1.5425

320

C ₇ H ₁₅

-C ₇ H ₁₅

CCH-CHCOO "K ⁺

5 "_

solid fuel

Vsrbindung R " ^C 7 ^H 15 R ₂ -C ₂ H ₅ R ₃ NC ₇ H ₁₅ '7 ^H 15 n ~ or ⁰ C No. ¹ OH -CHCH-CHCH ₃ 321 " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ O OH 1.4608 -C ₇ H ₁₅ " ^C 2 ^H 5 -CCH ₂ OCH ₂ COOH -CHCCl ₃ 322 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ OH 1.4630 323 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -CHCH-CH ₂ Solid substance 324 " ^C 7 ^H 15 -CH ₂ OH 1.4513 325 " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ OH-CH-CHO 1.4563 (T) VCRZN-C-SC ₂ H ₅ 326 " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ ( 1.4588 327 " ^C 7 ^H 15 1.4638

Connection no. R -C ₇ H ₁₅ -C ₂ H ₅ R3 328 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ O -C 329 -C ₇ H ₁₅ OH -C

330 331 332

333, 333 -

? 334

or

° ^c "

COOH

Semisolid

-C ₇ H ₁₅ " ^C 7 ^H 15 -C ₂ H ₅ -CCH-COOH 0 Il - ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CCH ₂ CH ₂ COOH 0 " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CCHCl ₂ " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ 0 -CCH-CHCOOH / ^cl NC " ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ - <N "_ /

1.4729 1.4920

OH

Connection no.

335

-C ₇ H ₁₅

-C ₇ H ₁₅

C ₂ H ₅

^e C

or

-CCH-CH,

1.4672

336

337

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₇ H ₁₅

-C-.H

7 ⁿ 15

C ₂ H ₅

C ₂ H ₅

-CCH

0 ^CH 3

HI

-C-C-CH,

1.4856

1.4673

338

-C ₇ H ₁₅

C ₂ H ₅

-CCH ₂ OCH ₂ COO · HNEt ₃ 1.4560

339

" ^C 7 ^H 15

-C ₇ H ₁₅

C ₂ H ₅

Il -C

COO · HNEt.

.30

339 - ny or ° C> -1.4870 340

-C ₇ H ₁₅

-C ₇ H

7 "15

-C ₂ H ₅

-CCH ₂ CH ₂ COO · HNEt ₃ 1.4830

341

-C ₇ H ₁₅

-C ₂ H ₅

-SO ₉ NH ₉

1.4660

connection

No.

342 343 344

" ^C 7 ^H 15

-C ₇ H ₁₅

-C ₇ H ₁₅

C ₇ H ₁₅

^C 7 ^H 15

C ₇ H ₁₅

C ₂ H ₅

C ₂ H ₅

C ₂ H ₅

-SNH,

NH

nj> ° or

1.4632

1.4670

1.4874

345 346 347

ro O ι

348

-C ₇ H ₁₅ " ^C 7 ^H 15. -C ₂ H ₅ -P £ ^% r3 ic _m 1.4670 ΙΗ ₄ ^Θ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -SO ₃ CH ₃ 1.4325 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ -SO ₂ NHC ₄ I- I ₉ 1.5264 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ 0 -P (OH) ₂ Glass

connection

No :

349

-C ₇ H ₁₅

R ₂

-C ₂ H ₅

or

-SO ₂ N (C ₂ H ₅ ) ₂ 1.4356

350

351

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₇ H ₁₅

° 7 ^Η 15

-C ₂ H ₅

-C ₂ H ₅

0 -CCH ₂ OCH ₃

1.5140

-CCH ₉ CH ₉ COO · H ₉ N ~ ^ NH

Δ Δ Δ /

351 352

¹ D

Semisolid

-C ₇ H ₁₅

-C ₂ H ₅

• O 1 0 ^ \ 'HN (C ₂ Hg) ₃ c ^ y -Cl ₀ - coo.

352 353

- 1.5472

" ^C 7 ^H 15

C ₇ H ₁₅

-C ₂ H ₅

SH

1.5464

354

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₂ H ₅

.SH

SH

stink

connection

No.

nj * ° or ⁰ C

355

356

-C ₇ H ₁₅

-C ₇ H ₁₅

356 - t ° _or ° C - 1.4467 357

" ^C 7 ^H 15

-C ₇ H

₇ H ₁₅

C ₇ H ₁₅

C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

-C (CH ₂ ) ₅ OH 1.4600

-CCH ^ CHCOO

HO

NC ₇ H ₁₅

^C 7 ^H 15

1.5730

358

" ^C 7 ^H 15

^C 7 ^H 15

-C ₂ H ₅

<ΐ

Cl

STILL.

Semi-solid ·

359

-C ₇ H ₁₅

^C 7 ^H 15

-C ₂ H ₅

-SCCl,

1.4880

360

-C ₇ H ₁₅

^C 7 ^H 15

-C ₂ H ₅

0

(I Il

• C-COH

1.4640

connection

No. ..

362

363

-C ₇ H ₁₅

-C ₇ H ₁₅

" ^C 7 ^H 15

" ^C 7 ^H 15

-C ₇ H ₁₅

-C ₇ H ₁₅

n3 T) ⁰ C

or

Il

-C (CH ₂ ) ₃ COH 1.4670

-CH (\

Il

1.4990

-CCCl-CClCOH 1.4780 ^

CH-CHCH

364

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ O, CH

1.4970

CH-CHCH

365

-C ₇ H ₁₅ " ^C 7 ^H 15

O C

1.4915

366

1.4922

connection

No.

367

368

369

-C ₇ H ₁₅

-C ₇ H ₁₅

" ^C 7 ^H 15

.30

369 - n ^ ^U or ° C - 1.4620

370

371

-C ₇ H ₁₅

" ^C 7 ^H _l5

-C ₇ H ₁₅

-C ₇ H ₁₅

" ^C 7 ^H 15

-C ₇ H ₁₅

^C 7 ^H 15

C ₂ H ₅

C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

OQ-CCCF

NH /

00 -CCO ^ · Al

1Λ

or

Semisolid

Semisolid

I'm ever.

00 -CCO

-C

Ca

1.2

tL ·

 I

371 - low ° C ^D

372

372 - njJ ° or ° C -

solid fuel

-C ₇ H ₁₅

HaIbfeststoff

-C ₇ H

7 "15

-C ₂ H ₅

-SO ₃ ·

HN (CH ₃ )

connection

No.

30

or

373

-C ₇ H ₁₅

374

374 - ny ° or ° C

375,376

-C-, Η

15

HaIbfeststoff

-2-ethylhexyl

-sec

C ₇ H ₁₅

" ^C 7 ^H 15

-2-ethylhexyl

• ^C 6 ^H 13

-SO ₃ . ΗΝ ( ^{/ λ} > 1.4630

-CCHCl,

0 CCHCl,

1.4664

1.4666

NJ I

377

sekC ₇ H ₁₅

-CCHCl ₂

1.4633

378

• sekC ₇ H ₁₅ -sekC ₇ H ₁₅ ~ ^C 2 ^H 5

-CCHCl ₂

1.4680

379

sec C ₇ H ₁₅ ~ ^C 7 ^H 15

-CCHCl ₄

1.4683

connection

No.

380

-2- ethyl hexyl

2-ethylhexyl

-C ₂ H ₅

j:

or

1.5487

381

-sek C ₇ H ₁₅

C ₇ H ₁₅

-C ₂ H ₅

/ SH

1.5638

382

sec C ₇ H ₁₅ -C ₈ H ₁₇

-C ₂ H ₅

SH

1.5567

383

-sekC ₇ H ₁₅

' ^C 2 ^H 5

it

-CCH ₂ CH ₂ COH

1.4612

384

385

-2-ethylhexyl

sec C ₇ H ₁₅

-2-ethylhexyl

^C 8 ^H 17

.C ₂ H ₅

.C ₂ H ₅

II

"CCH ₂ CH ₂ COH

0 'CCH ₂ CH ₂ COH

1.4653

1.4673

386

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

NCO

1.5440

^Verbi j. RR ₁ R "ηί ° or

^C 7 ^H l5 ^"C 7 ^H 15" ^C 2 ^H 5 Dickfluessiges

Oei

R ₃

C-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OH 0

η average = 7.7 One of the reactants was Carbowax 400 a

Product of Union Carbide Corporation in which the average molecular weight is 400 and η is an average of 7.7.

Compound No. RR ₁ R- ^ ⁰ _or

₁ R

^R 3

⁰ C

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

- ^^ ' '> ~ ^ CH ₃ - (CH ₂ ) _n .CH ₃ ,

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -0. S

η average = 11 j One of the reactants was Tergitol® 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no.

νξ ° or ⁰ C

389

" ^C 7 ^H 15

389 - nj * ° or ^e c - 1.5000

" ^C 7 ^H 15

-NHC-NC-SC ₀ H ₁ . // \\ .ι · 2 5

N-C, H

7 "15

C ₇ H ₁₅

390

-C ₇ H ₁₅ " ^C 7 ^H 15" ^C 2 ^H 5

- (CH ₂ ) gC-Cl

391

No

" ^C 7 ^H 15

C ₇ H ₁₅

-C ₂ H ₅

or

⁰ C

391

- (CH ₂ ) ₈ -O-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ 0

η average = 11 One of the reactants was Tergitol ^ 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no

30 or ^'11 D

392

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

392

- (CH ₂ ) ₈ -C -OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n OH

η average · 7.7 ®

One of the reagents was Carbowax®400

Product of Union Carbide Corporation in which the average molecular weight is 400 and η is an average of 7.7.

30

Compound Nr ^ R ^R 1 ^R 2 ^R 3 ¹¹ D ° ^der

" ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -O-CH ₂ CH ₂ OCCl

to ro 1

Connection no.

R ₁ R ₂ V ^or

OJ OJ 1

394 " ^G 7 ^H 15 - ^C 7 ^H 15" ^C 2 ^H 5

R ₃

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

η average = 7.7 Hines of the reagents Carbowax 4OO was a

Product of the Union Carbide Corporation in which the average molecular weight is 400 and η is an average of 7.7.

⁰ C

Compound No. r _{R] L} R ₂ n ° or

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

O CB ₃ - (C 1) _n -CH ₃

-O-CH ₂ CH ₂ OC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -O

η average = 11 One of the reagents was Tergitor ^ 15-S-7 ^

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no

³⁰ odor

-C ₇ H ₁₅

.C ₂ H ₅

O.CCl

Connection no

397

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

) Λ

⁰ C

397

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n 0H 0

to cn ι

η Average = (R) One of the reactants was Carbowax 4OO, a product of the Union Carbide Corporation in which the average molecular weight was 400 and η an average of 7.7.

Connection no

nj? ° or 'C

398

-C ₇ H ₁₅

-C ₇ H ₁₅ -C ₂ H ₅

η average = 11 One of the reactants was Tergitol "15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

398

CH 1 - (CH ₀ ) 1 - CH

NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -O 0

Connection No. 399

399

-C ₇ H ₁₅

H II

" ^C 7 ^H 15

CH.

-C ₂ H ₅

Il

⁰ C

NC ₇ H ₁₅

^C 7 ^H 15

η average = 7.7 One of the reactants was Carbowax 4OO, a product of Union Carbide Corporation in which the average molecular weight is 400 and η is an average of 7.7.

Connection Nr,

400

-C ₇ H ₁₅ -C ₇ H ₁₅

401

C ₇ H ₁₅

C ₇ H ₁₅

401 -

402

C ₇ H ₁₅

^C 7 ^H 15

402 -

403

- ^C 7 ^H 15

-C ₇ H ₁₅

30ο 30

ι 403 - Hq or

or

⁰ C

-C ₂ H ₅

-NH- (CH ₂ ) ₆ NCO

-C ₂ H ₅

NHC

CH

^N NH (CH ₂ ) ₁₁ CH ₃

-C ₂ H ₅

2CH ₂ CH ₂ OH -NH (CH ₂ ) ₆ NHCN '

H U) OD

CH ₂ CH ₂ OH

-C ₂ H ₅

-NH (CH ₂ ) ₆ NHC (CH ₂ )

30 R ^R l ^R 2 njj or

⁰ C

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

R ₃

-NH (CH ₂ ) ₆ NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) _n 0H

η average = 7.7 One of the reactants was Carbowax 4OO

Product of Union Carbide Corporation in which the average molecular weight is 400 and η is an average of 7.7.

30

Compound No. R. ^R l ^R: "

1 ^Λ 2

⁰ C

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

3 <2> rf3

κ ι j

-NH (CH ₂ ) ₆ NHC-OCH ₂ CH ₂ (OCH ₂ CH ₂ ) ₆ -0 "K.

η average = 11 One of the reagents was Tergitor ^iy 15-S-7

a product of Union Carbide Corporation of average molecular weight 508 where η is 9-13 and on average 11.

Connection no.

low ⁰ C

406

-C ₇ H ₁₅

C ₂ H ₅

NHC,

"0 (CH ₂ ),

.C

CH,

0 SC ₀ Hc

C-N-C

NC ₇ H ₁₅

^C 7 ^H 15

406 - n ** ° or ° C

407

C ₂ H ₅

° < ^CH 2 ^CH 2 °> 3

cw

0? ^C 2 ^H 5

^N " ^C 7 ^H 15 C ₇ H ₁₅

407 - n ^ ⁰ or ° C

219743

Q) TJ O

4- »• U (U

tnfH (O (Ωα)

cn

(fl

coi

O = O

^Ä CM

IO

in

O ι

XC

"Ti

r o

OO C O 3 • τ Ό C • π > -A Si Z U

σ o st

r-4

-143-

connection

No. R

or

412 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 413 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ 414 -C ₇ H ₁₅

416

~ ^C 2 ^H 5

415 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅

-C ₂ H ₅

-cnh / A-ch

NHCOCH.

-CNH-f ^ V-CH.

It

-CNH

CO Ο NHCO (CH ₂ ) ₃ C-CH ₃

CH ₃ C ₂ H ₅

NHCNH-CHCH ₂ Oh

(I

^ CH ₃ 0

NH 3 CN (CH ₂ ) ₆ 0H 0 -CNH-Z 1 V CH.

( ^CH 3> 2 NHCNHCCH ₂ Oh

wax

Viscous fluid

wax

wax

Viscous fluid

Connection no.

417

-C ₇ H ₁₅

C ₂ H ₅

CH,

P «r ^H 3> 2

NHCNHCCH ₂ CH ₂ Oh

paste

418

-C ₇ H ₁₅

-C ₂ H ₅

-CNH- ^ V-CH,

Ί ° / "A

NHC-O- ((CH +))

X /

cn.

viscose

Liquid

419

-C ₂ H ₅

(! V CH-

^J NHCOCH ₂ CH ₂ OC ₂ H ₅

paste

420

-C ₇ H ₁₅ - ^C 7 ^H l5 0 -CNiK ^'N> - CH.

NHC (OCH ₂ CH ₂ ) ₂ OC ₂ H _t

Viscous fluid

connection

No. R 421

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

CH-a NHCOCH ₂ CH ₂ OC ₄ H ₉

or

Viscous fluid

422

423

C ₇ H ₁₅

C ₂ H ₅

-C ₂ H ₅

Il

CH,

NHC (OCH ₂ CH ₂

CH,

CH,

Ί 9

NHC-OCHC ^ CH

Viscose fluid

.1

Viscose ^

Fluidity 'υ »

424

-C ₇ H ₁₅

Il

-CNH

CH,

Viscous: liquid

425

//. \ ^ CHo -C ₂ H ₅ -CNH- ^ ^{χΧ / Δ}

NHC0CHC0C ₄ H ₉ -n 6

Viscous fluid

connection

No.

η:

³⁰ or ⁰ C

426 427

-C

-C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

CH

iraco (CH ₂ ) ₃ Br

CH ₃ NHCO

Viscous fluid

IO

Viscous fluid

428

-C ₇ H ₁₅

C ₂ H ₅

-C

CH,

ti

NHC

CF.

Viscous Liquid _r

429

C ₂ H ₅

CH,

NHC

Cl

CH,

Viscous fluid

Connection no.

- ° 7 ^Η 15

431

432

-C ₂ H ₅

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅

-C ₂ H ₅

CH

NHCO (CH ₂ ) ₆ Cl

CH,

NHCNHC ₃ H ₇

CH, O

NHCOCH ₂ CH ₂ Cl

n ⁰ C

or

1.5260

1.5312

1.5339

45 »

433

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

ι "

Cl

wax

434

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

NHCOCH ₂ ^

Viscous fluid

Connection no.

nj * ° or ⁰ C

435 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

436

437

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

' ^C 7 ^H 15' ^C 7 ^H 15

NHCOCH

NHCOCH ₂ CH ₂ OCh ₃

NHC-OCH

1.5628

1.52526

1531

438

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

OCH! "

NHCOCH ₂ Ch ₂ CHCH ₃

1.5210

connection

No.

439

-C ₇ H ₁₅

· <: ₂ ^Η 5

It

NHCN (CH ₂ CH ₂ OCH ₃ ),

n ~ or ⁰ C

1.5282

440 441

-C ₇ H ₁₅ C ₇ H ₁₅ -C ₂ H ₅

7 ^H 15 ^C 2 ^H 5 3.0H

NHCNHCH

1540

1.5524

442

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

1.5277

Connection no.

443

444

445

-C, H

7 "15

'7 ⁿ 15

-C ₂ H ₅

C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

(I

-CNH

CH,

NHCNHCH ,, - ^

-CNH

or

Soft wax

Viscous Fluessigkext ^

Viscous Fluessigkext

446

C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

ti -CNH

CH

CH.

1.5355

connection

No. 447

-C ₇ H ₁₅

-C ₂ H ₅

CH,

or

Viscous fluid

448

449

C ₇ H ₁₅ -C ₂ H ₅

ff

NHC (OCH ₂ CH ₂ ) ₂ Cl

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

Il

-Cl

NHC (OCH ₂ CH ₂ ) 3 Cl

Viscous fluid

1.5251

450

CH

NHCSC ₂ H ₅

1.5461

connection

451

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

Il

-CNH

CH,

NHCSC ₈ H ₁₇

n3 ⁰ C

1.5269

452

-C ₇ H ₁₅

-CNH ^ VCH ₃

O NHC-Ο · / ⁷

1.5488

453

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

O- 1 ^ 3

NHC-0-f ^ S

1.5481

454

-C ₇ H ₁₅

-C ₂ H ₅

-CNH-f ^V V-CH

1.5481

Connection no.

455

456

-C ₇ H ₁₅

" ^C 7 ^H 15

R-i

-C ₂ H ₅

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

τξ ° or ° C

1.5472

Viscous fluid

457

-C ₂ H ₅

NHC-O - // 0

Viscous fluid

458

-C ₇ H ₁₅

"C-iH-i c -C> H

^I 15

CN

Il

C ₉ H

NHCNHCHCH ₂ Oh

Viscous fluid

connection

No. R

459 " ^C 7 ^H 15

R ₂

-CNlK ' ^v > - C

NHC-O- (cholesterol)

or

Viscous fluid

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

-O

Viscous fluid

461

-C ₂ H ₅

• CNH / '

1.5304

462

-C ₇ H ₁₅ -C ₇ H ₁₅

It

• C

CH,

NHCON '

 O

1.5416

connection

No.

463

464

-C ₇ H ₁₅

-C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

-CNH // ^

Il

NHC

CH

Cl

NHCOCH,

or

Viscous fluid

IO

Viscous fluid

465

-C ₂ H ₅

αϊ

wax

466

.C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

ti

-CNH-

CH.

CH.

NHC-N-NKJHCH

'CH *

1.5396

connection

No.

R \

or

⁰ C

467 468

469

-C ₇ H ₁₅ ^"C 7 -C ₂ H ₅ ^H i5

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

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

Il

-CNH

NHCOCH ₂ C = CH

ii

-CNH

NHCOCH ₂ C = CCH ₃

NHCOCH,

Wax 1.5325 1.5304

IO

M Ln

470

-C ₇ H ₁₅

-CNH ^ VCH,

1.5311

NHC

Connection no.

nr or ⁰ C

471 472

473

-C ₇ H ₁₅

" ^C 2 ^H 5

-C ₂ H ₅

-C ₂ H ₅

Il

^r V> - CH ..

CH

NHCOCHCH-CH,

1.5378

1.5250

Ln »J

Viscous fluid

474

• ^C 7 ^H 15

^C 7 ^H 15

-CNH- ^

CH ₃ ΟNHCOCH ₂ CH ^ ^X V-CH,

i.5484

connection

No.

nj: or

475

-C ₇ H ₁₅

-C ₂ H ₅

-CNH- ^

CH,

NHCOC ₁₁ H ₂₃

1.5124

476

477 " ^C 7 ^H 15

-C ₂ H ₅

C ₂ H ₅

NHCO (CH ₂ ) g CH-CH,

Λ-CH.

br

1.5172

1.5548

478

-C ₇ H ₁₅

C ₂ H ₅

NHCOCHCH ₂ N

/ ^C 2 ^H 5

C ₂ H ₅

1.5206

connection

No. 479

-C ₇ H ₁₅ ^"C 7 ^H l5" ^C 2 ^H 5

1 O

NHC

nj; or C ⁰

1.5288

480 " ^C 7 ^H 15

C ₂ H ₅

-CNH

CH.

NHC0C _A H _Q -n

1.5233

481 " ^C 7 ^H 15

C ₂ H ₅

NHCOC ₄ H ₉ -I

1.5220

482

H -CNI

CH,

0 C ^ H ₇ -η NHCN

C ₃ H ₇ -Ii

1.5278 zone

Connection no.

483

R ₁ R ₂

-C ₇ H ₁₅ -C ₂ H ₅

Il

-CNH

CH,

NHCNHC ₄ H ₉ -n

³⁰ or

⁰ C

Awake!

484 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

485 -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

• CNH

it

 CNH

NHCNHC ₄ H ₉ -I

Viscous fluid

Viscose as liquid °

486

C ₇ H-. e · ™ 7 1 5

Il

• C

CH,

Viscous fluid

487

-C ₇ H ₁₅

^C 2 ^H 5

NHCNH

K3

Viscous fluid

connection

No,

488

489

490

-C ₇ H ₁₅

-C ₇ H ₁₅

.C ₇ H ₁₅

.C ₇ H ₁₅

-C ₇ H

7 "15

-C ₂ H ₅

R3

-CNl

CH ₃ O

NHCN J

NHC

"/ ^C 2 ^H 5

C ₂ H ₅

"Β ⁰ C

or

Viscous Fluessigkext

1550

1.5329

491

-C ₇ H ₁₅

-C ₂ H ₅

Il

-CNH

CH, O "

NHCN '

, C ₄ H ₉ -H

C ₄ H ₉ -H

1.5234

connection

No.

492 493

-C ₇ H ₁ r

-C ₇ H ₁₅

C ₇ H ,. -C ₉ Hc ¹⁵

-C

5? ^CH 3 NHCNHCHCH ₃

II

C!

Il

NHCN

⁰ C

or

1,532 1.5280

IO

494

-C ₇ Hi ₅ -C ₇ H ₁₅ -C ₂ H ₅

CH.

NHCN

1537

495

ι · -C

CH,

C ₄ H ₉ -I

1.5236

connection

496

497

498

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

-C ₂ H ₅

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

^ς 3

ii

• CNH

 CNH

κ ^ CH (CHo) 9

NHCN

CH (CH ₃ ) ₂

CH ₃ O NHCOC ₂ H ₅

CH ₃ O NHCOC H ₇

njj ° or ⁰ C

PASTE

1.5280

1.5254

499

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

O NHCOC ₃ H ₇ -I

1.5258

connection

No.

500

501 502

-C ₇ H ₁₅

-C ₇ H ₁₅

Ri

-C ₂ H ₅

-C ₂ H ₅

NHC-N-C-SCOH

NC ₇ H ₁₅

2 ⁿ 5

OCH.

or

1.5401

1.5250

1553

ro

σ "

503

-C ₂ H ₅

-CNH-f

CH,

NHCNH- ⁷ ' ^v

Viscous fluid

connection

No. N_ or ⁰ C

504

-C ₇ H ₁₅ - ^C 7 ^H ₁₅

O -CNIII / ^X V CH ₃

ti

NHCNK- ⁷ '

1567

CJ

505

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

Il

• C

CH.

¹ ti

NHCI

Cl

Viscous fluid

506

-C ₂ H ₅

CH.

NHCi

1552

507

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

0 "

NHCNH,

Viscous fluid

connection

No. 508

509

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

R ₃

O -CNH / '^ n ₃ ^ ₂ H ₅

NHCNH - <_

C ₂ H ₅

CH,

nj * ° \ or ⁰ C

1542

ro

co

Viscous fluid

as a \

510

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

O NHCNH-C, V-CH,

1.5494

511

.C ₇ H ₁₅ .C ₇ H ₁₅ -C ₂ H ₅

o ³

NHCNHCH-

Viscous fluid

connection

No.

512 513 514

-C ₇ H ₁₅

R ₁ R ₂

-C ₂ H ₅

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

-C ₂ H ₅

NHCNHC ₂ H ₅

-CNH- ^

NHCNHCH ₂ CH ₂ NHCNh.

ny ⁰ or

1542

1.5311

Soft glass

NHC-O

NC-SC ₉ Hc Il ^{2 5} NC ₇ H ₁₅

^C 7 ^H 15

connection

No.

515

516

-C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅ .C ₇ H ₁₅ -C ₂ H ₅

-CNHh (^ y-CH ₃ O

NHCOCH,

n_ or ⁰ C

1.5398

if

OCNHj \ NHC-NC-SC ₂ H

CH-

-CNH--

NHCOCH ₂ CHC ₄ H ₉

NC ₇ H ₁₅

^C 7 ^H 15

1.5180

517

518

-C ₂ H ₅

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

30

518 - nn or ⁰ C - Soft glass

^J γ2 ^Η 5 NHCNHCH ₂ CHC ₄ H ₉

NHCNH (CH ₂ ) ₃ NHC

1.5246

^C 7 ^H 15

N-CH

7 "15

NHC-NC-SC ₂ H ₅

CH

connection

519

R ₂

" ^C 7 ^H 15

-C, H

15

-C ₂ H ₅

CH,

NHCNH (CH

of)

519 - IC or ⁰ C - Strong Viscous Liquid "· 0

NHC-NC-SC ₂ H ₅

NC ₇ H ₁₅ C ₇ H ₁₅

520

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

{i ⁰

NHC-NC-SC ₉ H

NC ₇ H ₁₅

C ₇ H ₁₅

520 - n {i ⁰ or ^o C - Viscose

Liquid

521

-C ₇ H ₁₅

-C ₇ H ₁₅ -C ₂ H.

-CNH- ^

CHO

NHCNH - / - ^ NHCfott-rv

CH.

C-N-C-SC NC ₇ ^2H 5 ³ 7 ^H 15 ^H 15 C

.30

521 - ny? or ^e C amber gel

connection

No.

  s

522

523

-C ₇ H ₁₅

C ₇ H ₁₅

C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅

-C ₂ H ₅

-cnh / ^v

I /

NHC

CH,

O -CNlK '

CH. O

NH (Wo)

Il

OC

30 or D

Viscous fluid

Soft glass

NHC-NC-SC ₀ H

CH.

Il ₇ H ₁₅ NC

^C 7 ^H 15

connection

No..

R,

524

2-Ae-thy-hexyl

- 2-ae thy I-

hexyl

-C ₂ H ₅

525

526

527

2-ethylhexyl 2-ethylhexyl -C ₂ H ₅ 2-ethylhexyl 2-ethylhexyl -C ₂ H ₅  2-ethylhexyl 2-ethylhexyl -C ₂ H ₅

528

2-Ae-thy 1-hexyl

-2-ethylhexyl

-C ₂ H ₅

529

2-Ae-thy 1-hexyl

 2-ethylhexyl

-C ₂ H ₅

__3 O

, - * - NHC-W -CNH-V \

CH.

n ».or ⁰ C

1.5429

NHC-O ^

CH

1.5430

1.5460 «*

C ₀ H _t

Sticky solid

1.5228

C ^ H ₇ -I

Ii / 3 7

C ₃ H ₇ -I

CH.

wax

connection

No.

530

531

-2-ethylhexyl

-2-ethylhexyl

-2-ethyl

hexyl

-2-ethylhexyl

_c "

2 5

_c "2 5

NHCNHC ₄ H ₉

-i

11

30 or

wax

1.5231

.fet OJ

532

533

 2-ethylhexyl

2-ethyl-hexyl

  2-ae-1-hexyl

 2-Aethylhexvl

.C ₂ H ₅

O -CNH-

Il

CH,

NHCOC ₂ H ₅

1.5265

1.5257

534

-2-ethylhexyl

-2-ethyl

hexyl

-C ₂ H ₅

-NHCOC ₃ H ₇ -Ii ^ CHo

1.5235

535

 2-ethylhexyl

• 2-ethylhexyl. Hexyl

1.5215 limit

connection

536

537

538

539

540

541

-2-ethylhexyl

-2-ethylhexyl

-2-ethylhexyl

2-ethylhexyl. Hexyl

-2-ethylhexyl

-2-ethyl

hexyl

2-ethylhexyl

2-ethylhexyl

-2-ethyl- C ₉ H

hexyl ^ά

-2-ethylhexyl

-C ₂ H ₅

-C ₂ H ₅

CH,

CH-

NHCOC ₃ H ₇

tu. or ° C

1.5216

1.5294

1.5290

1.5309

1.5475

1.5215 limit

Connection no.

542 -C ₈ H ₁₇ -C ₈ H ₁₇ -C ₂ H ₅ 543 " ^C 8 ^H 17 -sek C ₇ H ₁₅

12 .9

-C

ti

C!

CH,

// _xV ^ HCOC ₃ H ₇ CHo

τξ ° or ⁰ C

1.5209

1.5234

544

545

 2-ethylhexyl

• sec C ₇ H ₁₅

-C ₂ H ₅

" ^C 8 ^H 17

• ^C 8 ^H 17

-C ₂ H ₅

CH ₃

W NHC

CH.

- »ο

1.5275

1.5298

546

^C 8 ^H 17

CH,

1.5280

547

* ^C 8 ^H 17

₇ Η ₁₅ "C ₃ H ₇

V7

NHC -0 · /)

1.5260

Connection no.

548

^f -sek C ₇ H ₁₅ "C ₃ H ₇

ti NHCOC ₀ H

30 or

1.5455

549

550

-sekC ₇ H ₁₅

-sek C ₇ H ₁₅ -C ₃ H ₇

NHC

NHC

CHO

1.5455

1.5451

551

° 8 ^H 17 " ^C 8 ^H 17" ^C 2 ^H 5

CH.

1.5445

552

-sek C ₇ H ₁₅ -C ₂ H ₅

O NHCN-C-SCoH.

II ^J ' 1.5195 N-2-ethylhexyl

553

-C ₈ H ₁₇ -sekC ₇ H ₁₅ -C ₂ H ₅

1.5204

NC ₈ H ₁₇ ^C 8H ₁₇

Connection no.

554 " ^C 8 ^H 17 ~ ^secC 7 ^H 15 ~ ^C 2 ^H 5

-CNH-

(r

 ^ ζ-NHCNH- ^) Cl

30

1.5268

555

556

• ^C 8 ^H 17

• ^C 8 ^H 17

2-ethylhexyl

-sek C

-C ₂ H ₅

-NHC- ^ CH,

V yr- .NHCN-C-SC ₉ He -HNW // vT I Il ^{z α}

I NC ₈ H ₁₇

1.5466

1.5007

557 -C ₈ H ₁₇ -sekC ₇ H ₁₅ -C ₃ H ₇

0 NHCN-C-SC ^ H ₇

Il ^{3 7}

NC ₈ H ₁₇ SeKC ₇ H ₁₅

1.5180

558

" ^C 8 ^H 17 ~ ^sec C ₇ H ₁₅

-CNH C N)

-NHCN-C-SC-H ₇ η 3 7

CH,

NC ₈ H

₈ H ₁₇

SeKC ₇ H ₁₅

1.5185

Verbindu. No.

559

560

• 2-ethylhexyl

-2-ethylhexyl

-2-ethyl- " ^C 3 ^H 7 hexyl

2-ethyl- " ^C 3 ^H 7 hexyl

C ₉ H ₁ .

11 / 2-5

30 or 8.

Waxy white solid

1.5420

561

562

 2- Aethy

hexyl

 2-ethylhexyl

2-ethylhexyl

2-ethylhexyl

CH

C «H ₇ -i« / 37

-i

1.5210

1522

563

 2-ethylhexyl

2-ethylhexyl

1.5236

564

 2-ethylhexyl

2-ethylhexyl

-C ₂ H ₅ NHC-N

CH

CoH _7/37

^3H 7

1.5231

connection

No.

565

566

567

568

569

• ^C 8 ^H 17

2-ethylhexyl

-2-ethyl- -sekC ₇ H ₁ -hexyl /

-sekC ₇ H ₁₅ -C ₃ H ₇

-C ₈ H ₁₇

2-ethyl-hexyl

-sec

-C ₃ H ₇

-C ₂ H ₅

R ₃ O II it v \ O-NHC-I! / ^C 2 ^H 5 I ^ CH ₃ ^X C ₂ Hj O O Il .C ₂ H ₅ ι · -CNF O It - «ην» -ΓCH ₃ O -NHC-i ^ C ₂ H ₅ / ^C 2 ^H 5 I -cnf CH ₃ ^ C ₂ H ₅

CH

 O

CH,

or

⁰ C

1.5279

1.5278 zone

1.5278 zone

1.5270

1.5240

570

-2-ethylhexyl

" ^C 2 ^H 5

CNH-C

CH,

1.5410

Connection no. R -sekc ₇ H 571 2-ethylhexyl -sekC ₇ H 572 2-ethylhexyl

573

--COH

8 ⁿ 17

-2-Aet 1-

hexyl

574

^C 8 ^H 17

-2-ethyl- C ₉ H

hexyl *

575

" ^C 8 ^H 17

2-ethylhexyl. Hexyl

576

 2-ethylhexyl

or

1.5209

OC ti / ZW

CH

II

NHC-N

C ₃ H ₇ -I

opaque to light ^

casual, white wax

1524

_n . _K NHCNHC-H ₇ -I

1.5239

CH

3 0

CH

1.5262

1.5270

connection

No.

577

578

-2-ethyl-sec-C ₇ H ₁ , hexyl / 15

2-ethylhexyl

-C ₂ H ₅

Il

CNH- / ⁷

NHC

NHC-N

nj: or

 1.5304

1.5330

579

580

-2-ethyl. ' hexyl-sec C ₇ H ₁₅

2-ethyl-sec-C ₇ H ₁₅ hexyl

• cnhY /

NHC-n;

,H.

CH.

1.5305

1.5268

581

2-ethylhexyl

sec C ₇ H ₁₅

" ^C 2 ^H 5

(I NHC-N

CHO

1.5321

connection

No.

582

583

584

585

2-ethyl hexyl

 2-ethylhexyl

2-ethylhexyl. Hexyl

-C ₂ H ₅

-2-ethylhexyl.

-2-Aethylhexyi

-C ₂ H ₅

-2-ethylhexyl

 2-ethylhexyl

-C ₂ H ₅

1.5415

1.5406

1.5233

N-2-ethylhex-2-ethylhexyl

CH.

ο O SCoHc

ι ι ^J "I ^{L D}

M-CH-NHC-N-C

CH ₃ CH ₃

1.4991

-2-ethylhexyl

2-ethylhexyl

586

-C ₂ H ₅

• CNH ^

SC2H ".

ι »ι ->

NHCN-C

ti

1.5163

Compound NO,

587

588

-C ₂ H ₅

-C ₂ H ₅

or

-NHCN '

1.5162

Nn ^ _n W.

CH ₂ NHCN

SC ₉ H

I ^z C

Il N

1.4948

589

589 - £ or ° C - 1.5292

Il

SC ₂ H ₅

NHCN C

connection

No.

590

-C ₂ H ₅

NHCN

'2 ^Π 5

C ₂ H ₅

30 or

1.5212

591

-C ₂ H ₅

1.5153

592

-C ₂ H ₅

NHCOC ₃ H ₇ -i

CHO

1.5181

593

-C ₂ H ₅

NHC-O-) ^CH 3

1.5228

594

-C ₂ H ₅

0? ^C 2 ^H 5

ii I

-NHCN-C

NC ₈ H ₁₇

C ₈ H ₁₇ -t

1.5178

Connection no.

595

596

R ₂

-C ₂ H ₅

.G ₂ H ₅

R ₃

μ · NHCN-C

CH,

NC ₈ H ₁₇

} fft

 NHC-N-C

CH,

30 or

1.5447

1.5195

N-2-ethylhexyl

2-Aethylhexvl

597

-C ₂ H ₅

O ^SC 2 ^H 5

-CNH-f ^ V-NHC-N-C - '^ "xnw N-

-sec

1.5166

bo 598

-C ₂ H ₅

0 ^SC 3 ^H 7

NHC-N-C

1.5178

Ϊ-2-ethylhexyl

^C 8 ^H 17

connection

No.

599 600 601

602

-sek C ₇ H ₁₅

C ₂ H ₅

C ₂ H ₅

^C 2 ^H 5

R3 0

ii

-C

Il

 c

If <

NHC-N-C

SC ₂ H ₅

NHC-N-C

SC ₃ H ₇

NC ₈ H ₁₇

-sec

_Λ SC ₉ H ₁ -

S ²⁵

NHCN-C

i NC ₈ H ₁₇

NC ₈ H ₁₇

τξ ° or ⁰ C

1.5187

1.5176

1.5166

1.5184

Connection no.

603

-sekC ₇ H ₁₅ -sec C ₇ H ₁₅ " ^C 2 ^H 5

604

-sek C ₇ H ₁₅ -sec C ₇ H ₁₅ " ^C 2 ^H 5

605

-C ₃ H ₇

606

-C ₃ H ₇

NC ₈ H ₁₇ -Ii

Al 7 "^ * ^

JO or ⁰ C

1.5196

1.5178

1.5142

CH ₉ NHC-NC

' 'H

1.4930

connection

No..·

607

608

609

Ri

-sek C ₇ H ₁₅ -sek C ₇ H ₁₅

-C ₃ H ₇

I

it '

NHC-N-C

^SC 3 ^H 7

CHQ

NC ₈ H ₁₇

-sekC ^ H

⁰ C

1.5133

1.5244

1.5182

610

-sek C ₇ H ₁₅ -sekC ₇ H ₁₅

" ^C 2 ^H 5

SCOH ₇ I ³ 7

NHCN-C I

CH,

NC ₈ H ₁₇

-sec

1.5166

connection

611

612

613

R ₂

-sek CyH ^ J-sec C ₇ H ₁₅ " ^C 2 ^H 5

• sec C ₇ H ₁₅ -SeJcC ₇ H ₁₅ " ^C 2 ^H 5

-sek C ₇ H ₁₅ -sec CyH ₁₅ "C ₂ H

O? ^C 3 ^H 7

11 I

NHCN-C

NC ₈ H ₁₇

2-ethylhexyl SC ₉ H ₁ .

?, ι

NHCN-C

NC ₈ H ₁₇ ^t " ^c 8 ^H 17

O f ^C 3 ^H 7

NHCN-C

NC ₈ H ₁₇

-sec

η ³⁰ or T) IO ° c vO 1.5177

1.5202

1.5156

614

sekC ₇ H ₁₅ -sekC ₇ H ₁₅

NHCN-C

NC ₈ H ₁₇

1.5507

Connection no.

R ₁

615 -sec C ₇ H ₁₅ -sek C ₇ H ₁₅

R-

OC ^ H ₇ -I NHCN

^X CoH ₇ -I CH ₃ ^J '

IUO or C ⁰

1514

616

-sec C ₇ H ₁₅ -sec C ₇ H ₁₅ "C ₂ % 1.509

617

-sek C ₇ H ₁₅ -sec

.CH

NHCOCH

1.5164

618 -sec C ₇ H ₁₅ -sek C ₇ H ₁₅

H NHCOC ₀ H

₂ H ₅

1.5128

619

-sek C ₇ H ₁₅ -sek C ₇ H ₁₅ -C ₂ H ₅ NHCOC ₄ H ₉ -Ii ^CH 3

1.5145

219743

1-1 φ CM O m -. * O O cn Qo

οο

"η

fl | O = O

cd I ι

X.

O = O

ι *. 1-4 χ: SC SC s OO > O O χ; w ο- 55 -M Q) ti cn M ι (N O s O

O =

O =

"TI

in m r- / X SC SC < CM CM s \ O O O - < I I I   ..J m m EC SC / O O < M Φ yi φ > W tn i I \ m m > SC O O M φ Φ co O) I I

en O

-H U

O iH CM CM € M CM \O VO

cn

CM

vo

-191 -

219743

O O cn Qo

"Τ"

"n

r-l

in en

cn

vO

it

co- o = S ^:

SS SS OO r »O

o-o

s

SS O

(U U)

I ο-oci ι

m Ο r-l I T * SS Γ ·· SS SS ι SS SS cn r-l · OC it SS- OO OO υ SS O co O O co- o 00 co - I / SS ι O © (U Ο ~ υ 55 ^ S - E- O O) ι w - cn I cn SS O OsO SS f > O*

SS

O ι

«O r SScn o

SS en o

r-I

he c

t CN

CN so it vO

it

vo

- 19 2 -

Connection no.

628

R ₂

-C ₃ H ₇

-t

O? ^C 2 ^H 5

K i

NHCN-C I

CH.

NC ₈ H ₁₇

_n 30 or 1.5170

629

630

" ^C 8 ^H 17 -sec C ₇ H ₁₅

O? ^C 2 ^H 5 NHCN-C

NC ₈ H ₁₇

-sek C

0 ₍

NHCN-C

Il

CH,

NC ₈ H ₁₇

• ~ sec

^ -t

1.5239

1.5154

631

X / S / S

-C ₃ H ₇

1.5423

Verl. M

I- · VD

R " ^C 7 ^H 15 -SC ₂ H ₅ ! 3 OK τξ ° or ° C " ^C 7 ^H 15 -SC ₂ H ₅ -CNHSO ₂ Cl -C ₇ H ₁₅ O 0 Il -COC ₃ H ₇ -I 1.4488 -C ₇ H ₁₅ -C ₇ H ₁₅ -SC ₂ H ₅ -C-Tergitol 0 0 Il H 1.4564 0 -C-NHSO ₂ -ergitol -C- (CH ₂ ) ₂ CNC-SC ₂ H ₅ -C ₇ H ₁₅ 0 0 ^ CH ₃ 1.5583 -C ₇ H ₁₅ -SC ₂ H ₅ -COCHoCH C NC ₇ H ₁₅ ^C 7 ^H 15 -SC ₂ H ₅ CH ₂ CH ₃ ^C 7 ^H 15 • -C ₇ H ₁₅ 62-77 ° -C ₇ H ₁₅ " ^C 7 ^H 15 -SC ₂ H ₅ 1.4425 -C ₇ H ₁₅ 1.4954

Connection no

^or

1.5592

η average = (ty · _{Hines of the} reactants was Carbowax 350 a

 Product of the Union Carbide Corporation in which the average molecular weight is 350 and η is 6.2 on average.

Connection no.

η 1 ^e C

or

639

-C ₇ H ₁₅

" ^C 7 ^H 15 O -SCOC ₂ H ₅ -COC ₂ H ₅

1.4841

640 " ^C 7 ^H 15

641

" ^C 7 ^H 15

-C ₇ H ₁₅

-SCH ₂ CH ₂ Od -COC ₃ H ₇ -i

-SCH ₂ CH ₂ OH

Waxy semi-solid

Wax solid

642

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

CH

1.4621

643

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

 CC1

1.4613

'644

VD CTi

-C ₇ H

7 ^H 15 " ^C 7 ^H 15

C ₀ He Z 5

C ₂ H ₅

1.4568

.- 196 -

u • υ ο

ο OCTpO

00 00 CM cn ι-Ι sf <η O m O m m Γ *.   Sf- tr " m vO sr sf sr. sf sf

σ "

ο =

• Η I

ο>

4J I

8th-

CM

, 8th

o-o

O = U

O =

CSJI C ^ I

"η

U ι

ο t

"η

CM

υ ι

ιη

υ ι

r4

r υ ι

 Η

se

in

Γ ".

υ ι

in

υ ι

r-l

in1-4EC

in

in

ι-Ι

in sf

VO

sr vO

sf VO

OO Sf

ON Sf

VO

m vo

- 197 -

219743

U O st <ΰ O o νθ ¹ p «Η Q Γ- C si " rh

cn

CX) νθ

νθ

cn οο

O νθ νθ st

s

«Μ vD

safety-

cni

Pi I

O =

se ο

s

CM

EC

EC O

\ / 55

O I

CvII I

CvI O I

<n o

EC

CVI

se

CM O I

"CM

in

EC

r "·

r-l

EC O

O I

eil

r-l

EC

O ι

in i in __ | rH EC rH EC X r » O O O I I I

σ · CVI s C m in 3 vO vO T3 C ^ j · · - Z >

St in in in VO

vO

vO

- 198 -

.JU or connection% ^uue

Re x% x% . , '* "^

Λ ·· Λ * »ΛΟ O f%

M VO V £>

C ₇ H ₁₅ " ^C 7 ^H 15 -C ₂ H ₅ 0 NH | IU -CSC-NH ₂ -HCl ^C 7 ^H 15 " ^C 7 ^H 15 -C ₂ H ₅ 0 NH II H -CNHC-SC ₂ H _{5 n} NHC ₉ H-Vi ^C 7 ^H 15 -C ₇ H ₁₅ -C ₂ H ₅ -CN-C SCnHe

662 " ^C 7 ^H 15" ^c 7 ^H l5 " ^C 2 ^H 5 -CN | 1.4929

II / \

-cnJ

661 -C, H _1C- CiH, c -CnHc -CN-C 1.5156

663 " ^c 7 ^H 15 ' ^C 7 ^H 15" ^C 2 ^H 5 -CNH (CH ₂ ) ₆ -OH 1.4897

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

659 -C ₇ H ₁ K -C, H _1K -CnH _c -CSC-NH ₀ · HCl glass

660 -C, Η, -C1 H ₁ C -C ₀ Hc -CNHC SCnHe 1.5209

connection

No.

664

" ^C 7 ^H 15

-C ₂ H ₅

or

/ ^A V NHC-NCNC ₇ H ₁ C-

^C 7 ^H 15

.30

- r ^ ^U or ° C -

.5228

665

2-ethyl-2-ethylhexyl hexyl

-C ₂ H ₅

-C-CH ₂ CH ₂ COH • Et ₃ N

1.4899

666

 2-ethylhexyl

• ^C 8 ^H 17

-C ₂ H ₅

I /

-C (CH ₂ ) ₂ COH.Et ₃ N 1: 4879

667

-sec

• ^C 8 ^H 17

-CC ₃ H ₇ -I

1.4746

668

669

 2-ethylhexyl

-C ₇ H ₁₅

-2-ethyl _: hexyl

-C ₂ H ₅

-C ₂ H ₅

-CN (J)

Λ //

1.4930

Waxy semi-solid

³⁰

connection

No.

ⁿ D or

^R 1 ^R 2 ^R 3 ⁰ C

674 " ^c 7 ^H i5" ^C 7 ^H 15 " ^C 2 ^H 5" ^CC 15 ^H 31 Mud

''. '. '. °;. '' '' -

675 " ^c 7 ^H l5 - ^C 7 ^H l5" ^C 2 ^H 5 " ^CC 3 ^H 7 1.4740

, , , '. '. '. , , '

to

ο 0

, 676 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -CC ₄ H ₉ 1.4746

670 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -CCH ₃ 1.4793

671 " ^c 7 ^H l5" ^C 7 ^H 15 " ^C 2 ^H 5 -U-COC ₂ H ₅ 1.4757

^: '· ^:. '. '. <>. ''-'.' · . '; - '^;

^^ _A η -. , .-.

672 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5" ^C ( ^CH 2 ^ 16 ^ 3 ^/ - 'Mud

''. ; '. '"'. ^; . 0 " - '';. , .-. ' · ^ '. '- \ --- j: - - - ο

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

219743

U (U Ό O

ο υ cn pe

CM

r *.

(0

co

cn

Γ * CM co CM cn rs. r- r- »

s

CM U

cn S3 CM cn σν S3 r-i U U O U o = u O ^ U r-i U I I O O = U o-u I

J ¹ I

tr " S3 CM m S3  S3 S3 ³³ . CM U SC CM CM CM CM U I CM U U U U I U I I I I

m tr "I i u-i _. ir " m »N · ^^ S3- U -C ₇ H ₃ -C ₇ H ₃ -CyH ₃ S3 r «. U -C ₇ Hj -C ₇ H ₁

m m in m u-> "n r-l iH r-l S3 S3 S3 53 S3 S3 S3 r> » rs. rs. rs. rs. U U U U O U U I I I I I I

cnC .3 -a C H ^ 3

fs

rs. vo

co

fs

O r-l CM cn QO CO OO co VO VO VO vO

- 202 -

Connection no.

684

-C ₇ H ₁₅

R;

0 t'-CC ₆ H ₁₃

30

° C

or

1.4724

685

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

-CC ₇ H ₁₅

1.4730

686

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

Il -CC ₈ H ₁₇

1.4730

687

" ^c 7 ^H l5" ^C 2 ^H 5

Sdhlamin

688

" ^C 7 ^H 15" ^C 2 ^H 5 -CC-NC-SCH

ii

2 "5

NC ₇ H ₁₅ C ₇ H ₁₅

1.4932

689

" ^C 7 ^H 15

-CSC (CH ₃ )

1.4872

219743

O O CO Q o C

νθ Γ ··

ON

00 sf

st

sf

vO vO

sf

O vO

<\ N

CO m ιη O 33 O 33 m "η 33 33 33 C CM C CM 33 33 8th CM CM 8th 8th CM CN O = O 8th O O = ο = ο 8th 8th O = O ο = -ο D ^ O 3 ~ Ο ο-υ ο = ο δ O = O O = O I I O = O O = O CM δ I I ι I Ο-Ο I

CNl

1

m in m m m m X X SS X X  SS X CM CN CN CN CN CN CVJ O O O O O O O I I I I I I

33 33 33 33 OO m νθ O O ο O ι I ι I

o ι

CO

33

r »

 O

33

OO

4J I

* 00

νθ O

ιη 33 ^ O

CQ I

33 o

CO I

U] I

Qn 3

JQ V.

O ν θ

tr "

νθ

σ vo

CO sf m νθ ON ON ON ON VO νθ νθ

- 204 -

η ³⁰

Compound _ο ⁿ D ^or

No - H.' H H 'C.

0 °.

697 "" V "" ^C 7 ^H 15 " ^C 2 ^H 5 -CCOC ₂ H ₅ 1.4817 -

9? ,

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

-tC ₈ H ₁₇ " ^C 7 ^H 15 - ^C 2 ^H 5 II-CCOC ₂ H ₅ " ^tc 8 ^H 17 -C ₄ H ₉ -C ₂ H ₅ tf. -CCOC ₂ H ₅ -tC ₈ H ₁₇ " ^C 6 ^H 13 -C ₂ H ₅ n! -CCOC ₂ H ₅ it I -sek C ₈ H ₁₇ -sek C ₇ H ₁₅ -C ₂ H ₅ -CCOC ₂ H ₅ -tC H ₉ -sekC ₇ H ₁₅ -C ₂ H ₅ | I I -CCOC ₂ H ₅

699 -tC ₈ H ₁₇ " ^C 6 ^H 13" ^C 2 ^H 5 -CCOC ₂ H ₅ 1.4821

700 -sekc ₈ H ₁₇ -SeIcC ₇ H ₁₅ - ° 2 ^Η 5 -CCOC ₂ H ₅ 1.4752 ι

701 -tC H ₉ -sekC ₇ H ₁₅ " ^C 2 ^H 5 -CCOC ₂ H ₅ 1.4789

702 -sekc ₇ H ₁₅ -sekC ₇ H _i5 " ^C 1 ^H 3 -CCOC ₂ H ₅ 1.4770

703-secC ₇ H ₁₅ -sekC ^ - " ^C 2 ^H 5 -CCOC ₂ H ₅ 1.4745

connection

No,

R-.

or

704

705

706

707

-tC ₈ H ₁₇ " ^C 8 ^H 17 -C ₁ H ₃ -sekC ₇ H ₁₅ -C ₇ H ₁₅ -C ₃ H ₇ 2-ethylhexyl 2-ethylhexyl -C ₂ H ₅ -C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

CCOG ₂ H ₅

1.4809

ο Hc

κ CC CCOC ₂ H ₅

0 -CCH ₂ COC ₂ H ₅

1.4748

1.4782

1.4822

708

sec C ₇ H ₁₅ -C ₇ H ₁₅ " ^C 3 ^H 7

-CNH · //

NHCN C SCoH-

Il ³ '

1.5166

N-sekC ₇ H ₁₅

^C 7 ^H 15

709

"2-ethyl-" C ₇ H ₁ hexyl "

-C ₂ H ₅

-CCOC ₂ H ₅

1.4784

connection

No.

2-ethylhexyl - ^C 2 ^H 5 -CCCC ₂ H ₅ 2-ethylhexyl -C ₃ H ₇ -CCOC ₂ H ₅ " ^C 7 ^H 15 -C ₄ H ₉ O? -CCOC ₂ H ₅ 0 -CNH- ^ O Il. · N HCl C ϊ-CS-CaHq II * ^y N-secC _? H ^} 7 ^H 15

n ° or ⁰ ° C

1.4837

1.4818

1.4748

1.5152

15

vO

to

^C 8 ^H 17

- ^C 3 ^H 7

-CCOC ₂ H ₅

1.4808

sec C ₇ H ₁₅ -C ₈ H ₁₇ -CH ₂ SCH ₃ -CCOC ₂ H ₅

1.4960

Connection no.

716

R ₂

-C ₂ H ₅ -C ₂ H ₅ " ^C 2 ^H 5

11 H -CCOC ₂ H ₅

³⁰ or ° C

1.4883

717

718

-2-Aethylhexvl

-sec

^C 6 ^H 13

• ^C 8 ^H 17

CCOC ₂ H ₅

1.4788

_ö SC ₂ H ₅

{J} - NHCNC-N-secC ₇ H ₁₅

^C 8 ^H 17

718 - nj * ⁰ or ° C - 1.5305

719

-sek C ₇ H ₁₅ " ^c 7 ^H l5" ^C 3 ^H 7

0? ^C 3 ^H 7 CNC-N-sekC ₇ H ₁₅

C ₇ H ₁₅

719 - n2 ° or ^e C - 1.5307

720

sekC ₇ H, c

-2-ethylhexyl

1.4776

connection

No.

or

721 722

723 724 725 726

727

sekC ₇ H ₁₅ 2-ethylhexyl -C ₃ H ₇ 2-ethylhexyl " ^C 6 ^H 13 -CH ₂ S ^ ⁷ CH ₃ -C ₇ H ₁₅ -C ₂ H ₅ ^C 7 ^H 15 " ^C 7 ^H 15 -C ₂ H ₅ C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅ s ek C ₇ H ₁₅ -Λ, -CH ₂ C ^C 7 ^H 15 ^C 7 ^H 15 -C ₂ H ₅

II H-CCOC ₂ H ₅

-CCOC ₂ H ₅

-CCOC ₂ H ₅

-CCOC ₃ H ₇

I -ScOC ₃ H ₇ -I

-CCOC ₂ H ₅

1.4785

1.4983

1.5295

1.4766

1.4738

1.4814

1.5008

Connection no.

728

729 730 731 732

-C ₇ H ₁₅

CH-

" ^C 7 ^H 15 -C ₂ H ₅ -COJ ^ Jj) -Cl " ^C 8 ^H 17 -C ₁ H ₃ f, -CCOC ₂ H ₅ -C ₇ H ₁₅ -C ₂ H ₅ -CCOC ₂ H ₅ - ^C 8 ^H 17 -C ₃ H ₇ 0 ° 11 "-CCOC ₂ H ₅ -C ₇ H ₁₅ -C ₂ H ₅ ι »Μ -CCOC ₂ H ₅

-30 or ⁰ C

slurry

1.4752 1.5255 1.4757

1.5398

733

-C ₇ H .. c - (CH ") rtOCHo

1.4803

734

-SeJcC ₇ H ₁₅

-C ₂ H ₅

ο?

nil -CCOC ₂ H ₅

1.4739

Connection no.

735 736

737

738

.C ₅ H ₁₁ S (CH ₂ ) ₂ -C ₈ H ₁₇ -C ₂ H ₅

C ₇ H ₁₅ - (CH ₂ ) ₃ OCH ₃ -C ₅ H ₁₁ SeIcC ₇ H ₁₅ 2-ethylhexyl -IC ₄ H ₉ ^C 7 ^H 15 -CH ₂ CH-CH ₂ -C ₂ H ₅

739 CH ₃ O (CH _{2) 2} 0 (CH _{2) 3} -C ₇ H ₁₅ -C ₂ H ₅

-CCOC ₃ H ₇ -I

II-CCOC ₂ H ₅

ι / Β -CCOC ₂ H ₅

u II -CCOC ₂ H ₅

-CCOC ₂ H ₅

30 or 1.4898

1.4772

1.4794

1.4857

1.4777

740

'741

-2-ethylhexyl-O (CH ₂ ) ₃

-C, H ₇

-C ₈ H ₁₇

-CCOC

2H5 " ^C 2H ₅

0 ° -CCOCH (CH ₃ ),

-CCOC ₂ H ₅

1.4723

1.4792

30

Connection no.

742

743

NJ M N>

744

745

746

747

748

O O

-sekC

7 ^H 15

sekC ₇ H ₁₅

2-ethylhexyl -IC ₃ H ₇ κ H -CCOC ₂ H ₅ 2-ethylhexyl -C ₇ H ₁₅ -CCOC ₂ H ₅ 3 " ^C 7 ^H 15 -C ₅ H ₁₁ -CCOC ₂ H ₅ 2-ethylhexyl -C ₂ H ₅ Il '-CCOC ₂ H ₅ " ^C 7 ^H 15 -C ₂ H ₅ -CCOC ₂ H ₅ -C ₂ H ₅ it I -CCOC ₂ H ₅ -C ₂ H ₅

or

⁰ C

1.4764

1.47211.4757

1.4915 1.4943

1.4750 1.5105

ΓΟ

CJ

NJ

Connection ^ ₀ ^or

R Ri R «Ro

No. - ^ JL _mm £ _mm J ^ ⁰C

/ ³ fi

749 -C₂H₅-Yourself₂)₄ ~ ^ΰ Ί \% "^C2^H5 -CCOC₃H₇-I 1.4740

^ H ₃ «*

750 " ^C 8 ^H 17 -CH ₂ " ^ " ^C 2 ^H 5 -CCOC ₃ H ₇ -I 1.4936

        -. '0 ..'. ". .. '. '

751 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -CSCH ₃ 1.4948 ^

752 ^"C 7 ^H l5" ^C 7 ^H 15 ^"C 2 ^H 5 -CSC ₂ H ₅ 1.4922

753 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -CSC ₃ H ₇ 1.4916

754 " ^C 7 ^H 15" ^C 7 ^H 15 " ^C 2 ^H 5 -CSC ₃ H ₇ -I 1.4894

connection

No.

755 756

757

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

758

-C ₇ H ₁₅ - ° 7 ^H 15

-C ₇ H ₁₅ -C ₇ H ₁₅ -C ₂ H ₅

-C ₇ H ₁₅ " ^C 7 ^H 15 ~ ^C 2 ^H 5

R3

O -CSC ₄ H ₉

O II -CSC ₄ H ₉ -

O -CSC ₄ H ₉ -I

-CSC ₈ H ₁₇

or

⁰ C

1.4898

1.4892

1.4879

1.4860

759

* ^C 7 ^H 15 " ^C 7 ^H 15" ^C 2 ^H 5 1.5287

760

" ^C 7 ^H 15

1.5250

761

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

Cl

1.5366

connection R * i Il L JL R ₃ No. -2-ethyl -2-ethyl 0 ° -UcOC ₃ H ₇ -I 762 hexyl hexyl -CqHy si -2-ethyl -2-ethyl • J I -CCOC ^ H ₇ -I 763 hexyl hexyl -CHf © ft -sek C ₇ H ₁₅ " ^C 8 ^H 17 -CCOCaHc 764 -C ₂ H ₅  ft Cl ^ V -sekC ₇ H ₁₅ κ II -CCOCnHc 765 CH ₃ 2 " ^C 2 ^H 5 0 -C ₇ H ₁₅ - (CH ₂ ) ₃ N (C ₂ H ₅ ) -CCOC ₃ H ₇ -I 766

"j) or

1.4800

1.4749

1.5052

1.5298

1.4786

sec C ₇ H ₁₅

'2 ^Η 5

ί -CCOC ₂ H ₅

1.4909

sec C ₇ H ₁₅

-C ₈ H ₁₇

ο II

-CCOCoHc

1.5114

connection

No.

769

CH.

CH

II H-CCOC ₂ H ₅

"30

ⁿ D or

1.5632

770

-Ch ₉ -ZO) -C ₉ H

-CCOC ₃ H ₇ -I

1.5526

771

Q-CH ₂ -C ₇ H ₁₅ -C ₂ H ₅ -CCOC ₃ H ₇ -I

1.4882

772

sekC ₇ H ₁₅

Hf -CCOCH.

1.4784

773

-sek C ₇ H

⁷ 15

" ^G 6 ^H 13

κ Ι -CCOC ₃ H ₇ -I

1.4730

Connection no.

774 775

777 778

• sec C ₇ H ₁₅ " ^C 8 ^H 17

• sec C ₇ H ₁₅

-sek C ₇ H ₁₅ -C ₈ H ₁₇

-sec

-sek C ₇ H ₁₅

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

II -CNH-sec-C ₇ H ₁₅

OCH

-CNH-C

CH,

H.

N.

/

CH,

or

1.4756

1.4766 1.5215

1.5145

1.5219

Determination of the butterfly-suppressing activity The butterfly-suppressing activity of the above compounds was examined with respect to various epidopic species as follows:

1. salt marsh caterpillar (Estigmene acrea (Drury))

A solution of the compound to be tested was prepared by dissolving the compound in a 50-50 acetone-water solution. A piece of sorrel leaf (Rumex crispus) about 2.5 cm wide and 4 cm long was inserted into the test for 2-3 seconds. ¹ immersed immersion and then placed on a wire mesh to dry. The dried leaf was placed in a Petri dish containing a piece of moistened filter paper and infested with larvae of larvae in stage 5 appearance. The death of the larvae was noted 48 hours later. If surviving caterpillars were in the dish, synthetic medium was added to the dish and the larvae were observed for an additional 5 days to detect any delay effects. The primary concentration of the compound in the test solution was 0.05% by weight.

2. Spotted larvae of the cabbage white butterfly (Trichoplusia ni (Hübner)) The procedure for the cabbage larvae larvae was the same as for the salty brood larvae except that a cotyledon of hyacinth squash (Calabacita abobrinha) of the same sorrel dimension was used. The primary assay concentration for this assay was also 0.05% by weight of the solution to be tested.

3. Tobacco caterpillar (Heliothis virescens (F.))

Larvae of the tobacco caterpillar were used here according to the method described for the salt marsupial caterpillar, with the exception that a lettuce leaf (Latuca sativa)

the dimension of the sorrel blade was used in the previous experiment. The primary concentration was 0.1% by weight of the compound to be tested

- 218 -

219743

in the solution.

Table II lists the results of the test series with respect to the compounds of Table I. The results are expressed as LDc ₀ values which fixes the concentration of the compound to be tested in which a 50% mortality of the insects was obtained in the experiment. The results of Table II were obtained as follows.

For any Lepidopteran species, each compound was used in the above primary concentration. Solutions in which less than 50% mortality is obtained are indicated in the table by the greater than sign (^). Compounds in which a 50% mortality was obtained in the above-indicated primary concentration are characterized by the primary concentration alone. Compounds and solutions in which more than 50% mortality was obtained in the test series were subjected to further experiments until the concentration corresponding to a 50% mortality of the insects was obtained. This value is given as the LD ₅ value in Table II.

Phytotoxic trial series

Phytotoxic experiments were performed on cotton (Gossaypium hirsutum) and hyacinth squash (Calabacita abobrinha) seedlings. The plants were planted in Kaiser No. 1059 aluminum beds of 15 χ 23 χ 7.5 cm pulled and treated. Each bed contained a row of cotton and a row of squash with 6 to 8 plants per row. The plants were grown in a greenhouse and treated after about 8 days when they were about 5 cm high.

The compounds to be tested were dissolved in a 50-50 acetone-water solution. The solutions to be tested were then prepared using a Ducon-S avko Model 3400

- 219 -

219743

"219 linear spray table sprayed on the beds at a spray ratio of 0.56, 1.12, 2.24 and 4.5 kg ai / 748 l / ha. The treated plants were placed in a greenhouse and so watered that the leaves did not get wet.

One week after the treatment, the treated plants were examined and the phytotoxic effect visually classified between 0 and 5:

0 = no injury

1 = slight injury

2 = mild to moderate injury

3 = mediocre injury

4 = moderate to severe injury

5 = severe injury or death

Table II also lists the phytotoxic results of this series of experiments with reference to the compounds of Table I.

- 220 -

2197 43

Table II

Compound Lepidopteriζide Phytotoxic effect

Cotton pumpkin

No. effect CL TBW SMC «MMM O ₇ oil ^ 05 1 0,003 0.04. 2 0 _; 008 0 _; 006 O ₇ 03 3 O ₇ 0024 0.0016 > O ₇ O8 4 0.016 0 _f 009 0.15 5 O ₇ 003 0.005 0.05 6 0 _; 001 0.0008 O ₇ 02 7 0 _f 002 O ₇ 0009 0.02 8th O ₇ 0009 0,002 0.01 9 0 _r 0007 0.0007 0.02 10 0.005 0,002 > O, O5 11 0, 008 0,002 > 0.05 12 O ₇ OOl 0 _f 003 > Q, 05 13 0 _; 003 Oj 005 > Q, 05 14 0,003 0,008 > 0j05 15 0 _f 008 0,008 > 0.05 16 0,008 O ₁ 002 > 0.05 17 O ₇ OOl O ₁ 003 > 0.05 18 0.05 0.005 -NjO ₁ 05 19 0,003 0,002 "> Q05 20 0,008 0,003 > 0.05 21 0.01 0.0008 ^ a 05 22 0005

1.2 1 2 1.2 1 Iro 0 0 2 0 0 2 O 0 r-l 0 1 2 0 0 3 0 1 r-l 0 0 0 0 0 0 1 4 4 1 4 4 0 0 2 0 0 2 0 1 4 0 1 4 0 1 4 0 0 3 1 3 5 0 2 5 1 3 5 1 3 5 0 2 5 0 2 5 0 1 5 0 2 5 1 2 5 1 2 5 1 3 5 0 2 4 1 2 5 0 1 3 1 3 4 0 2 4 1 2 4 0 1 4 1 2 4 0 1 3 0 2 5 0 2 5 1 2 4 0 1 3 0 1 2 0 1 2 0 0 1 0 0 1

- 221 -

219 7 43

Table II

Compound lepidoptericidal phytotoxic effect

No effect cotton pumpkin

SMC CL TBW 23 0,003 0.0005 > 3.05 24 >), 05 o oi _r > 0 _; 05 25 0 _T 03 0.005 > ° ° 5 26 vp 05 0.01 > O ₇ O5 27 0 _f 005 O ₁ OOl > 0.05 28 > 0.05 Oj 003 0.05 29 0,002 0 ^ 002 > 0 _f 05 30 0 _f 005 0,002 0 _; 05 31 0.005 O ₁ 003 0 ^ 05 32 0.001 0,002 O ₇ oil 33 0008 0 _f 01 ^ 05 34 0.005 0 ^ 02 > 0.05 35 0.01 0 ^ 0005 -P ₁ 05 36 0.005 0 _; 002 37 0,002 O ₁ 002 0 _f 05 38 _0r 003 0.005 > 0 _T 05 39 > Q, 05 O ₁ I > 0.05 40 0.001 O ₁ OOl OjOl 41 0,003 0.03 -D ₁ OS 42 0.001 O ₁ 002 0.05 43 0,002 O ₁ 002 > 0.05 44 > 0.05 CL 03 > °, 05

1.2 1 2 1.2 1 2 O rh 3 O 2 4 O ι 3 O 1 2 O 2 4 O 2 3 1 2 3 O 1 2 O 1 3 O 1 3 O 1 3 O 1 2 O O O O O 1 O r-4 2 O O 1 O r-i 2 O 1 3 O 1 3 O 1 3 O O 1 O O 1 1 1 2 1 2 3 ο rh 2 1 2 3 O 1 2 O 1 3 O O 1 O O 2 O 1 3 1 2 4 O O 2 O 1 3 1 3 5 1 4 5 ο O 1 O 1 2 O 2 3 1 2 5 O 2 5 rh 3 5 O 1 3 O 2 4

219743

Table II

Compound lepidoptericidal phytotoxic effect

No effect cotton pumpkin

SMC CL TBW

45 0.01 0.0005 0.05 46 ο _; 01 0,002 ^ 05 47 o _f 001 0.001 0.03 48 o _r 005 O ₁ OOl 0.03 49 O ₁ 0003 o _f 0002 0.05 50 O ₇ 0003 O ₁ 0003 qO5 51 O 001 o _; 001 o, 05 52 O ₁ 005 O ₁ 003 53 O ₇ 008 O ₇ 005 54 O ₁ OOS o, 005 55 0,002 o, 002 56 O _f 001 o _} 0003 0.02 57 0.001 o _; 0003 O ₁ 02 58 0 ^ 02 ο 0005 o, 05 59 0,002 o _; 0005 o, 05 60 0003 0,002 > ^ 05 61 O ₁ OOS α 005 O ₇ 05 62 O _T 0008 O ₁ 001 o 05 '63 o _t 001 O ₁ 005 > D, 05 64 o _t 005 o _r 008 > O, 05 65 O 0002 0.0005 ⁰ I ⁰²

0.002 o, 03

1.2 1 2 1.2 1 2 1 2 5 1 3 5 0 0 1 0 r-l 2 0 1 3 0 2 4 1 2 4 r-l 3 5 r-l 2 5 r-l 3 5 1 3 5 1 3 5 0 2 5 0 2 5 0 1 2 0 0 2 0 0 tH 0 0 1 0 0 0 0 0 2 0 1 2 0 1 2 1 2 3 1 3 4 0 2 4 1 2 5 0 2 3 0 3 5 0 1 3 ο r-l 3 0 0 0 0 0 0 0 2 5 0 3 5 0 i-l 2 0 1 2 0 0 1 0 0 2 0 0 1 0 0 1 r-l 2 5 1 3 5 0 1 3 0 2 3

- 222 -

219 7 43

Table II

Compound lepidoptericidal phytotoxic effect

No effect cotton pumpkin

⁰ y SMC CL TBW 67 of 001 0,002 0 _; 05 68 ⁰ l 0008 0 _; 005 0 _; 05 69 ⁰ T 0003 0,002 > 0.05 70 ⁰ T 001 0002 ^, 05 71 ° F 001 0 _T 0005 0 _; 05 72 ⁰ T 0008 0 _; 002 0.05 73 O ₁ 002 0 _; 003 0.06 74 °) 002 0 _; 002 0 _; 03 75 ⁰ l 003 0 _; 03 ^; 05 76 ° r 003 0.03 ^ j 05 77 O, Oil 0,002 > 0 _; 05 78 of 002 0 _; 0005 0.05 79 ° r 005 0,002 > 0; 05 80 ° r 002 0.0005 0 _; 01 81 ⁰ T 003 0,002 O ₇ 05 82 ⁰ T 008 0,002 > ₇ O5 83 - ⁰ l 005 0 _; 003 >), 05 84 ⁰ T 001 Oj 0003 ^, 05 85 of 005 O _f 0003 0.03 86 ⁰ l 002 O _f 0008 > 0.05 87 O 002 O _f 002 > 0.05 88 003 O 0002 > 0.05

ti 1 2 1.2 1 2 O O O O O O O r-l 3 O 2 5 O 1 3 O 1 5 O r-l 3 O 1 4 O 1 4 O 1 4 O O i O 1 2 O O 1 O O 1 O O O O r-4 O O O O Ό O O O O 1 O O r-4 O O r-l O O 1 O r-4 2 O 1 3 O O O O O O O O r-4 O O r-4 O O O O O 1 O r-4 3 ρ 1 4 O O 1 O O 1 O 1 4 O r-4 5 O O 3 O O 2 O O O O O O O O 3 O 1 4 O O 3 O O 4

- 223 -

219743 -224-

Table II

Compound lepidopteric phytotoxic effect effect cotton pumpkin

SMC CL TBW 89 0 _f 001 0 _; 002 O ₁ OS 90 O ₇ OOl 0.0002 _0r 04 91 0.0003 0 _f 0002 * OjOl 92 0.005 03 > °, 05 93 0.001 Oj 001 > 0j05 94 0 _f 005 0,002 > _0r 05 95 0 _f 002 Q.0008 > 0j05 96 OjOOl Oj 0003 > 0j05 97 0.0008 OJ 0008 ^, 05 98 O ₁ OOl o _t ooi 12:05 99 0 _; 002 Oj 0005 > 0 _; 05 100 0 _? 003 Qj 0005 0.05 101 o _f ooi α 002 0.05 102 Oy 0003 0,002 (^ 06 103 <Ö.O5 0,002 α 03 104 Oj 003 (} 002 0.05 105 0.005 0,002 OJ 05 106 0.005 Oj 0005 0.05 107 0 _f 003 Qj 0008 0.05 108 0 _f 002 ο _Λ οοι > ° Fo5 109 0 _T 003 0,002 0.05 110 O oil 0.0005 > 0 ° 5

1/2 1 2 1/2 12

0 0 0 0 0 0

0 0 1 0 0 1

0 0 0 0 0 1

0 0 0 0 0 0

0 0 2 0 13

0 0 1 0 0 1

0 0 0 0 0 1

0 24 1 3 5

0 0 0 0 0 0

0 1 3 0 1 3

0 0 1 0 0 2

0 1 3 0, 1 4

1 2 4 1 3 5

0 0 0 0 0 1

1 2 4 1 2 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 14 0 2 4 0 0 10 0 2 0 1 2 0 1 3 Ό 2 4 0 3 5 0 0 2 0 0 2

- 2 25 -

9743 SMC CL TBW - ^ 25 1 2 1.2 1 2 0008 Oj-05 > 0.05 Table II 0 0 0 0 0 21 0.001 0 _; 0003 °; 05 0 2 0 1 3 Compound Lepidoptericides No. Effect Oj.005 0.303 O ₇ OS 0 0 0 0 Ö 0 002 0 _; 0005 0 _? 05 0 2 0 1 3 111 O ₁ 003 O ₁ OOe > °, 05 0 0 0 0 0 112 0 _f 002 0 _; 003 <ÖjO5 0 0 0 0 0 113 0 _? 002 0.002 I > 0 05 0 0 0 0 r-l 114 0 _f 001 0 _? 0005 <PjO5 0 1 r-l 2 3 115 _0r 05 O ₇ 002 > \ 05 0 0 0 0 1 116 0002 0 001 0 _; 05 0 0 0 0 0 117 0 _f 0005 0 ^ 0005 12:03 0 1 0 0 2 118 o _T oooi 0 _T 0005 12:03 Phytotoxic effect of cotton pumpkin 1 3 1, 3 5 119 0 * 0003 0.001 I 0.05 1.2 3 4 1 4 5 120 0.05 0.0008 I 0.002 0.001 Qy 05 <QjO5 0 1 0 CM r-l 0 0 i-l O 3 1 121 0 ^ 0005 0.0005 0.03 0 1 3 1 2 4 122 0 _f 0008 O ₁ OOS ^ 05 0 r-l 2 1 2 5 123 o _t ooi Oj 0Ol <$, 05 0 0 0 0 0 0 124 125 0 _T 005 Oj 0005 Q ₁ 05 0 0 1 0 1 2 126 0002 0 _f 002 <Q, 05 0 0 0 0 0 3 127 0,008 _0r 002 0.05 0 0 0 0 0 0 128 ο 003 0,002 <P.O5 0 0 1 0 1 3 129 0 130 0 131 0 132 0 1 0 0 0 0 0 0 0 0 0

219743

Table II

Compound Lepidoptericides' Phytotoxic Effect

_No. Effect cotton

134

SMC CL TBW

133 OjOOl 0 _; 005

003 Oj 001

> 0j

135 0 ^ 0008 0.0005

136 0 ^ 0002 0 ^ 003 0 ^ 05

137 0 _f 001 0 _; 03> o _f l

138 0 _f 005 OjOl> o, O5

139 0 003 0 _T 002 <p, 05

140 0 _T 002 0.001 <(} 05

141 0 ^ 0005 0 _f 0005 0,05

142 O _r oi 0.002 0 ^ 05

143> P.05 0.03 α 05

144 0 001 0 _T 002 <J>, 05

145 0 ^ 0003 0,0005 <a05

146>) _? 05 0 _T 005 0.05

147 0 _t 005 O _f oo2 ^ 05

148 0 _r 005 0 ^ 0005 ^ 05

149 0 005 0 ^ 002 0,05

150 0 ^ 0001 0 ^ 0003 <QjO5

151>) _T 05 0 _f 008 <φ, 05

152 0 _f 002 0.0003 0.05

153 0 _T 002 0.001 O _T 08

154 0 ^ 0003 ^ 001 0 _T 02

1.2

1.2

0 0 1 0 0 2

0 0 0 0 0 1

0 0 2 0 13

0 0 0 0 0 1

0 0 0 0 0 0

0 1 2 0 12

0 0 0 0 0 1

0 0 1 0 0 0

0 0 2 0 0 1

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 1 0 0 2

0 0 0 0 0 0

0 0 2 0 0 2

0 0 1 0 0 1

0 0 0 0 0 0

0 12 0 13

0 0 0 0 0 0

0 13 0 2 3

0 0 0 0 0 0

0 0 1 0 0 1

- 227 -

219743

Table II

Compound Lepidoptericides No. Effect SM ("MB" · : CL TBW Phytotoxic effect of cotton pumpkin 1 2 1.2 1 2 "05 > QtO5 ".05 m 0 0 0 0 0 155 ^ 03 a 03 0 0 0 0 0 1 156 > DjO5 > 0 _τ 05 0 ^ 04 0 0 0 0 0 1 157 ^ 05 > Q, 05 0j05 0 0 0 0 0 0 158 0 _f 05 O ₁ OOS ^ 05 ο 0 0 0 0 1 159 x ^ os 0 _t 05 "05 0 0 1 0 0 1 160 > (> 05 0.03 0.05 0 0 0 0 0 0 161 ⁰ T ¹ Xi ₁ 05 O. 0 0 0 0 0 162 ι 0.01 OjQ4 0 0 0 0 0 0 163 α 008 ι > 0jO5 0.05 0 0 1 0 0 1 164 ^ 05 ^ 05 12:05 0 0 1 ο 0 1 165 > CL05 ^ 05 ^ yo5 0 0 1 0 0 1 166 Upper Austria, 05 ^ 05 12:05 0 1 2 0 0 1 167 S3.05 ι 12:01 0.05 0 0 0 0 0 0 168 O ₁ O ₃ 0 ^ 05 0 0 0 0 0 0 169 ^ 05 ^ 05 > AO5 0 0 0 0 0 0 170 > .O5 0.4 > Q, 05 0 0 0 0 0 0 171 0 ^ 003 ^ 001 > QfO5 0 0 0 0 0 0 172 Ο, οι Oj 003 X ^ 05 0 0 0 0 0 0 173 OQ.05 0 ^ 03 > QjO5 0 0 1 0 0 0 174 > Q, 05 ^, 05 > ° .05 0 0 1 0 1 2 175 0.05 > \ 05 Xl, 05 0 0 1 0 0 1 176 0

- 228 -

219743

Table II

Compound lepidoptericidal phytotoxic effect

_No. Effect Cotton Kurbis___

SMC CL TBW Ul ' i 1 Ul A 2

177> o _; 05 o _; 2> 0 05 0 0 1 0 0 1

178> 0 _r 05 0 _; 05> 0.05 0 0 1 0 0 1

179> 0.05 O _? C1 Xi05 0 0 10 0 1

180 0.005> °. 05 X105 0 1 3 0 12

181 Oj 05 0 _T 01 X} 05 0 0 0 0 0 1

182 0.03 0 _r 008 XiO5 1 2 4 12 4

183>0.05> 0 _f 05 O ₇ OS 0 0 0 0 0 0

184 0 _T 01 0 _? 003 X ^ 05 0 0 0 0 0 0

185> Q, 05 o _f 5 "cyO5 0 0 0 0 0 0

186> 0 _? 05 ο 05> QjO5 0 0 0 0 0 0

187> 0 _f 05 0 ^ 01> (} 05 0 0 0 0 0 0

188> 0.05 0.5 X105 0 0 1 O ₀ 0 0

189 0.003 0.01 XlO5 0 0 1 0 0 1

j 190 Xi05 0.008 XiO5 0 0 0 0 0 0

191 O ₁ oil 0 _? 15 X ^ 05 0 2 3 0 2 4

192> ^ 05 0 01 XiO5 0 12 0 13

193 0j4 0 0 1 0 0 2

194 0.2 0 0 2 0 0 2

195 ö _f 001 0 ^ 002 X ^ 05 0 12 0 1 3

196 XJ, 05 0.01> ^ 05 0 12 0 0 2

197 0 _r 2 0 0 1 0 1 2

198 0.5 0 12 0 0 1

- 229 -

219743

Table II

Compound Lepidoptericides No. Effect

SMC CL TBW

199> 0 _; 05 0.2> PjO5

200 0 _r 01 Q ₁ 0025> p _? 05

201 <yo5> 0.05> ° .O5

202 OjO5

203 ^ 05> Q, 05 0 ^ 03

204> CL05 Q ₁ I ^ 05

205> 0 _? 05 O ₁ I> 0.O5

206 0 ^ 03 0.03> 0 _r 05

207 0 _? 03 0.03> 0 _? 05

208 0 ^ 03 0 008

209 ₁

210> o _r 05

211 O ₁ OS

> 0 _T

"05

212 O ₇ Ol 0 002 0 _T 05

213 »j5>0j05> 0 _T 5 214

215

216 0 ^ 008 01,005> Q ₎ 05

217 0.05> a, 05 ^ 05

218 0 ^ 05 0 ^ 003 ^ 05

219 (^ 005 0,008> Q, 05

220 0 ^ 03 0 ^ 004 0,05

Phytotoxic © effect cotton pumpkin

  1.2

1.2

1 2 4 1 3 5

1 3. 5 2 3 5

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 ·. 0. 0

0 0 0 0 0 0

0 0 1 0 0 1

0 0 0 0 0 1

0 0 0 0 0 1

0 0 0 0 0 0

0 0 2 0 0 1

0 0 10 12

0 12 0 12

0 0 0 0 0 2

0 0 1 0 0 1

- 230

219743

'230'

Table II

Compound lepidoptericidal phytotoxic effect cotton gourd

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

221 0 01 OjOO4 0 ^ 05 0 0 1 0 1 2

222> 0 _t 05 0j3 ^ 05 0 0 0 0 0 0

223 0j003 0 (308> 0 _? 05 0 0 0 0 0 0

224 0 _η 03 0 ^ 002 ^ 05 0 0 0 0 0 1

225 O ₁ oil 0.03> 0 _; 05 0 0 1 0 0 2

226 0 ^ 005 0.005> 0 _? 05 0 0 1 0 0 1

227 O ₁ 03 0 ^ 0008> 0 ₇ 05 0 12 0 13

228 0.003 0.002 0.05 0 1 2 0 1 2

229 0 ^ 01 0 ^ 009> 0 ^ 1 0 13 0 2 4

230 0.003 0.001> U 13 5 13 5

231 O ₁ OOl 0 ^ 0005>), 1 2 5 5 15 5

232 O ₁ OOl 0 _; 0005> Ρ.1 0 "2 5 Oo 2 5

233 0 | 003 0 0008 >>_; 1 1 4 5 0 3 5

234 0 _t 002 0.002 0.1 0 2 5 0 2 5

235'0 ^ 003 0 0008 al 1 4 5 0 3 5

236 0 _? 003 0,0005 ^ 1 1 3 5 1 3 5

237 0 ^ 002 O ₁ OOOS ^ O ₁ I 1 5 5 1 5 5

238 0 _T 002 0,003> ^ 05 0 0 0 0 0 1

239 0 ^ 03 0.03> C ^ 05 0 0 2 0 0 2

240 O ₁ 03 0.03 ^> 0.05 0 12 0 1 3

241 ^ ₁ OS 0 ^ 005> (^ 05 0 0 3 0 1 5

242 0.01 0.005 ^ O ₇ OS 0 0 2 0 1 5

- 231 -

219743

Table II

Compound Lepidoptericides No. Wirkur.q SMC CL 0.005 TBW Büunv Phytotoxic effect wool pumpkin 2 1.2 1 2 0.03 0 _} 01 >). 05 1.2 1 3 0 1 4 243 12:03 Qj 03 > p, 05 0 0 3 0 1 4 244 O ₇ 008 O ₇ 005 O ₇ 05 0 1 3 0 1 4 245 0 _; 05 0 002 > ^ 05 0 1 2 0 1 3 246 12:01 12:01 >), 05 0 0 1 0 0 2 247 0 _; 01 > ⁰ j05 > 0.05 0 0 0 0 0 0 248 > 0 _f 05 V 0.05 0 0 0 0 0 0 249 > °; 05 0.005 > 0.05 0 0 0 0 0 0 250 0.01 0 _; 03 >) J05 0 0 2 0 1 4 251 ^ 05 12:03 12:05 0 0 1 0 0 1 252 ".05 0 ^ 05 > °} 05 0 0 0 0 0 0 253 >), 05 >, 05 _{> 0)} 05 0 0 0 0th 0 0 254 y. 05 12:15 0 ^ 05 0 " 0 0 0 0 0 255 >), 05 > Q, 05 0 0 0 0 0 1 256 >), 05 ^, 05 > 0) l 0 0 0 0 0 0 257 >) ₇ O5 > 0:05 > ^ I 0 0 0 0 0 0 258 >), 05 0.03 0.01 0 0 0 0 0 0 259 0,008 0.05 > S ⁰⁵ 0 0 0 0 0 1 260 ^ 05 > ^ 05 > O., O5 0 0 0 0 0 0 261 O ₁ Os 0.005 > Ο, Ο5 0 0 0 0 0 0 262 O ^ 005 0005 > O ₇ O5 0 0 1 0 1 2 263 0005 ^> AO5 0 1 1 0 0 1 264 0 0

- 2 32 -

219743

SMC 1 CL TBW Table II 1 2 1.2 1 2 αθ3 0 ^ 003 > ° ₀ O5 0 2 0 1 3 > Q, 05 γ > 0 ^ 05 0 1 0 1 2 0.005 0 / J03 > 0 _} 05 0 0 0 1 2 Compound Lepidoptericides No. Effect 003 0,002 > O, O5 0 2 0 0 2 ^ 03 > O, O5 XJj 05 0 1 0 1 2 265 0003 0 ^ 002 12:03 Phytotoxic effect of cotton pumpkin 1 3 0 1 4 266 o _v 003 0,002 0.05 ul 2 5 1 2 5 267 0002 0002 12:05 0 2 4 1 3 5 268 0.005 0002 o 05 0 2 4 1 3 5 269 0 002 0.001 0 ^ 05 0 1 2 0 1 3 270 0001 0 0005 0.05 0 0 2 0 1 3 271 0,003 0.0008 > J05 0 0 2 0. 1 3 272 0.001 0002 > J05 0 1 2 0 1 2 273 0003 O ₁ OOl 12:05 0 1 4 0 1 5 274 0,003 0.001 "05 1 1 2 0 1 3 275 α 003 0.0005 0.05 1 1 4 0 1 5 276 0.001 Oj 005 0.001 0 ^ 0005 0.06 0 ^ 05 0 2 2 4 4 0 0 2 1 5 5 277 12:01 0,002 0.05 0 1 2 0 1 3 278 0 ^ 001 0.0008 12:05 0 ' 4 5 1 4 5 279 0 ^ 001 0.0002 >, 05 0 1 3 0 3 5 280 0 001 0.0002 0 _T 05 0 0 2 0 0 3 281 282 I 0 - 2. 33 - 283 0 284 1 1 285 0 286 1 0 0

219743_ ₂₃₃ .

Table II .

., · Phytotoxic effect

Compound Lepidoptenζide .- _cotton pumpkin

No. >

effect

287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308

SMC CL TBW

0.005 CL 0.002 0.002 0.001 0

0.0005 0.02 0.0005 0.02 0 0.0008 0.03 0 0.005

O ₁ OOl 0,0005 OjOl

0.0002> 0, ( ι ι

0001

0 ^ 002

0 ^ 0005 o.OOl 0,05

0 ^ 002 0.002 0.05

0.003 0.005 »5.05

0 ^ 008

O ₁ OOS

0 _? 003 ».05

0.003 0.03

0.003 0.001 0.03 0 _f 03 0.01> \ 05

0.05 0.05> 0.05

> 0.05 » _v 05> P _T 05

> 0 ^ 05> o, O5 ^ 05 y \ 05 ^ 05> 0,05

> 0.05 0.04

0.05 1/2 0 0 0 0 0 0 0 0 0 0 0 Ο 0 0 0 0 0 0 0 0 0 0

1/2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

1 0 0 0 0 0 0 0 0 0 0 0 1 2 0 0 1 0 0 0 1 2

2 4 1 0 0 0 0 0 1 0 0 1 2 3 0 1 2 1 0 0 2 3

- 2 34 -

219743

309 Wi ι k dopterizide TBW Table II Phytotoxic effect 1 Le 2 ul pumpkin 2 310 SMC MM «· ^ 05 cotton j] 0 0 0 1 1 Preliminary Lepi 311 > O ₇ O5 : CL Qj 05 ul 0 0 0 0 0 » 312 > P _T 05  »J 05 > 0.05 ο 0 0 0 0 0 313 OJ 05 > 0.05 > 0j05 0 0 0 0 0 0 314 0 _f 04 > XC5 / Oy 04 0 2 4 1 0 5 315 Oj 002 O ₁ 05 > Ο, Ο5 0 3 5 3 3 5 316 0 ^ 002 0003 O ₁ OS 0 3 5 2 4 5 317 <3, OO8 0005 > oy05 2 0 0 0 3 0 318 0 ^ 04 <p _t 008 > 0 _? 05 1 0 0 0 0 r-l 319 0.05 0 04 > αθ5 0 0 Ό 0 0 0 320 >>. 05 (^ 04 0 2 3 1 0 4 321 O ₁ 002 > o.O5 0 0 1 0 2 2 322 0005 0 ^ 002 0.02 1 2 4 2 0 5 323 0002 0 008 0.03 0 · 3 5 1 3 5 324 0 ^ 002 0 ^ 002 0.05 1 r-l 2 0 3 2 325 O ₁ OOS 0 ^ 03 > O ₇ O5 r-l 0 0 0 1 0 326 >>, 05 0.01 > 0.05 0 0 r-l 0 0 0 327 12:03 O ₁ S 0.03 0 2 5 2 0 5 328 0 ^ 002 0 ^ 003 0.05 0 2 5 2 3 5 329 0 ^ 003 O ₁ OOl 0.04 1 2 5 2 3 5 330 0 ^ 002 0,002 > 0.05 1 1 3 1 3 3 0 ^ 002 0 ^ 003 > 0.05 1 0 0 0 2 0 O ₁ 002 0 ^ 003 0 0 - 235 - 0 ^ 005 0

2 197 0,003 43 -235- 1 2 1.2 1 2 O ₇ 005 Table II 0 0 0 0 0 Connection no ig Lepidoptei effect >>, 05 rizide 0 0 0 0 0 SMC CL 0,008 TBW Q 0 0 0 0 331 0 001 0.1 > 0 _? 05 0 0 0 0 0 332 0 ^ 002 oji > °, ⁰⁵ 0 0 2 4 5 333 ^; 05 "05 > 0.05 0 0 0 0 0 334 0 _; 03 0 _; 002 ^ 05 0 0 0 0 0 335 ^; 05 0. _y 002 » _; 05 3 5 1 2 5 336 > 0:05 0 _? 005 > 0.05 3 4 1 2 3 337 0.03 0,008 > 0j05 1 3 1 2 3 338 0.005 0.009 > 0 _? 05 2 3 1 2 3 339 O ₇ 005 0 _; 005 > 0:05 Phytotoxic effect of cotton pumpkin 0 1 0 1 2 340 o _r 03 0.1 O ₇ 03 1.2 2 3 1 2 4 341 0.01 0003 > 0 _; 05 0 0 0 0 0 0 342 O ₇ oil 0,008 o _? 05 0 1 3 1 2 3 343 O ₇ 002 0009 > 0 _; 05 0 0 0 0 0 1 344 >), 05 Oj 002 > X05 0 0 0 0 0 0 345 0,002 0.05 o 03 0 1 4 0 1 3 346 0 _? 03 0.005 > 0 _{) 0} 5 0 2 4 0 2 3 347 0.03 O ₇ 005 ^ 05 0 1 4 1 2 3 348 0 _; 005 0,003 0 ^ 05 1 1 2 1 2 3 349 > 0 _; 05 > 0:05 1 0 2 1 1 2 350 O ₇ 005 O ₇ 03 0 351 0 _; 03 > °; 05 0 352 0 005 > 0.05 0 0 0 0 0 0 0 0 0 0 0

219743

Table II

Compound Lepidoptericides * Phytotoxic effect

_No. Effect cotton pumpkin

1/2 12 1/2 1 2

0 0 0 0 0 0

0 0 0 0 0 0

0 3 4 1 2 5

0 12 0 2 4

0 0 0 0 0 0

0 0 0 0 0 0

0 2 3 1 2 2

0 13 12 3

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 1 0 0 1

0 0 0 0 0 0

0 0 0 0 0 0

0 12 0 12

0 0 0 0 0 0

0 12 0 12

0 0 2 0 0 2

0 13 0 12

0 0 10 12

0 2 4 1 2 3

0 12 0 12

SMC °> CL TBW 353 0 _} 03 °, 002 OJ 05 354 0 ^ 002 °, 002 OjOl 355 0,002 O, 001 0 ^ 05 356 0.005 ) 005 V ₃₃ 05 °> 357 O.03 >> 005 0 _; 05 358 0.05 °> 05 0/05 359 0,002 °; 005 12:05 360 0.005 0th 002 12:05 361 OjOl ° 7 003 S3.05 I 362 O ₁ 008 ⁰ y 008 363 0 ^ 05 °; 002 OJ 05 364 0005 ⁰ y 002 OJ 05 365 > 0.05 2 > 3j05 366 > 0j05 °; 05 0 05 367 0,003 005 > D _; 05 368 "05 ⁰ y 03 OJ 05 369 0,003 ° j 003 0 _; 05 370 0005 0 005 0 _; 05 371 0,003 °; 008 OJ 05 372 0002 °; 002 ^ 05 373 0,002 ° i 005 ^ 05 374 0001 002 > 0.05

219743

Table II

Compound Lepidoptericides No. Effect

Phytotoxic effect Cotton pumpkin

SMC CL TBW

375 Qj 002 0 002>). O5

376 0 003 0.005 0 05

377 0 ^ 002 0 _; 0005 0.05

378 Ci 003 0 _? 005 0.05

379 Qj 002 0 003 0 _? 05

380 CL 002 0.0003 0.05

381 0 002 0.003 -50.05

382 0 ^ 002 0 _; 0005 0.1

383 Q. 001 0 _; 002 0.05

384 O ₇ 002 0.0008 0 05

385 CL 002 0.0005 0.05

386 CL 016 0 _t 0016>). 08

387 0.003 0 009 0 _; 15

388 0.0024 0.006 0.03

389 0.004 0.0008>) _? 1

390 ο, 05 0.03 0.05

391> o, O5> 0 _; 05>) _; 05

392> o ^ O5 ^ 05 0-05

393 0.01 0.01> 0.1

394 0.05 0 _T 03

395 0.05>) _? 05

396 0.01 0.005> 3.1

1/2 0

1 0

2 0

0 0

0 0

1 3 0 0

1/2 0

1 2 0 0

0 0 0 0 0 1

0 0 0 0 0 1

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 1 2 1 2 3

0 0 0 0 0 1

0 0 1 0 0 2

0 0 0 0 00

14 4 1 4 4

0 0 3 0 11

0 0 2 0 0 2

0 0 0 0 0 0 0 12

0 0

- 238

219743 _

Table II

Compound Lepidoptericides' Phytotoxic Effect

No effect cotton pumpkin

SMC CL TBW 1.2 1 2 1.2 1 2 397 o, o5: > 0:05 0 0 0 0 0 2 398 OJ 05 > O ₇ 003 0 1 3 0 2 3 399 0 01 OjOi 0 _? 03 0 0 0 0 0 0 400 0 ^ 05 0 04 0 0 0 0 0 0 401 Oj 002 / 0 002 1 2 5 1 3 5 402 0.05 ^ 05 0 0 0 0 0 0 403 0001 0 _; 002 0 2 4 1 2 5 404 12:03 0008 0 0 0 0 0 0 405 α 03 12:01 0 0 0 0 0 1 406 ° _; 03 12:03 ο 0 0 0 0 0 407 0 _? 03 0008 0 0 0 0 0 1 408 12:03 0 _; 03 > o.O5 0 0 0 0 0 0 409 0,003 0.005 >), 05 0 0 0 0 0 0 410 0.0008 0.002. j 12:05 0 0 0 0 0 1 411 0.005 / Ό. 002 I 0.04 0 1 3 1 3 4 412 / O ₇ 003 0,002 »05 0 0 2 0 0 2 413 0,003 0 001 12:04 0 0 0 0 0 0 414 0.005 0 _; 003 12:04 0 0 1 0 0 1 415 0002 0001 12:04 0 1 3 0 1 2 416 0005 O ₇ 002 Qj 04 0 0 0 0 0 1 417 0003 0 _? 0025 ^ 05 0 0 0 0 0 0 418 0 _; 008 0003 > ° / 05 0 0 0 0 0 0

- 239 -

219743

Table II

Compound Lepidoptericides No. Effect

419 420 421 422 423 424 425 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440

SMC CL TBW

002 0.0025 0.05 3.05 Phytotoxiache effect cotton pumpkin

r ⁰¹

j, 005

"7 0.03

0 _? 005

12:01

0005

0.005

0.01

12:01

0.003-0 _; ü05 0.002

0.03 0.05

008 0.003 <O, 01

0. ₍ 001 0.05

0.01-0.002> 0.05

0.01 0.005> D.O5

0 01 0,002> 3.05

0.03 0.005 S3.O5

0.002 0.001 NO.

0

0.002> 0.05

0.005> 0.05

O ₇ 005> aO5.,.

O ₇ 03> P.O5

0.002> Q, 05

0.003 0.001 Q.05

0.005 0.001> 0 _; 05 0 _f 003 0.002 0 _; 003 0 ^ 003 O ₇ 003 0.003 1/2

0 0 0 0 0 0 0 1 0 0 0 0 0 0

0 0 0 0 0 0 0

1/2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

2 0 0 2 2 2 0 2 2 0 0 0 1 2 2 0 0 0 1 0 1 2 0

-

219743

-240-Table II

Compound lepidoptericidal phytotoxic effect

Cotton pumpkin

SMC CL TBW 1.2 1 2 1.2 1 2 441 0 _t 005 0002 ^ 05 0 0 0 0 0 0 442 0 003 ° _; 005 > 0 _? 05 0 0 0 0 0 2 443 0 _f 003 0 _; 005 »05 0 0 0 0 0 0 444 0008 0 _; 01 > XO5 0 0 0 0 0 0 445 0001 0.01 > O, O5 0 0 0 0 0 0 446 0003 0008 >), 05 0 0 0 0 0 0 447 0 _; 008 12:01 ^ 05 0 0 0 0 0 0 448 0 _; 005 0 005 ^ 05 0 0 0 0 0 1 449 0008 0 005 ^ 05 0 0 0 0 0 0 450 0005 0005 ^ 05 0 ρ 0 0 0 0 451 0 _; 005 12:03 0.05 0 0 0 0 0 0 452 0001 0 _; 001 0.05 0 0 0 0 0 0 453 0 _; 002 0.005 O ₁ OS 0 0 0 0 0 0 454 0 _; 001 0 ^ 003 >, 05 0 0 0 0 0 0 455 0,008 0 ^ 002 0 06 0 0 1 0 0 1 456 0 _; 002 0 _f 002 0.05. 0 0 0 0 0 0 457 0 _; 005 0 ^ 02 12:05 0 0 0 0 0 0 458 0 _; 005 12:01 >, 05 0 0 0 0 0 0 459 0 _f 008 12:01 OJ 05 0 0 0 0 0 0 460 0y003 O ₁ 002 >), 05 0 0 0 0 0 0 461 0 _f 005 O ₁ 002 >), 05 0 0 0 0 0 0 462 0.005 0 002 "; 05 0 0 0 0 0 0

- 241 -

219743

Table II

Compound Lepidoptericides No Effect Phytotoxic Effect Cotton Gourd

SMC 0 CL TBW 463 0 _; 005 ° j 005 0 05 464 0 002 005 0 ^ 05 465 0005 °; 002 ^ _} 05 466 0 _f 003 °> 002 OJ 05 467 0003 0th 002 ^ 05 468 0,002 0th 002 >) _} 05 469 Oj 002 0th 002 470 0002 003 0 _; 05 471 Oj 002 °; 005 >). O5 472 Oj 003 ⁰ l 005 >> 05 473 0002 ⁰ y 002 >>, 05 474 0002 °; 002 0.05 475 0,002 ° r 005 ^ P, 05 476 0,002 U \ } 002 12:05 477 0.005 ⁰ l 002 > Pj 05 478 0 _? 003 °) 002 ^ 05 479 0 ^ 005 ⁰ y 01 12:05 480 0,003 ⁰ l 002 >) _? 05 481 0 ^ 003 002 0.03 482 0008 ⁰ l 003 0.05 483 Oj 005 002 ^ ₁ OS 484 O ₁ 003 002 > 3, Ο5

1.2 1 2 172 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r-l 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0

- 242 -

219743

Table II

Compound lepidoptericidal phytotoxic effect

No effect cotton pumpkin

SMC CL TBW ul 1 2 hl 1 2 485 O ₁ CHB 0,002 ^) ₁ O ₅ ρ 0 0 0 0 0 486 0005 0 002 > & 05 0 0 0 0 0 0 487 0001 "05 0 0 0 0 0 0 488 0 003 0,002 0 ^ 05 0 0 0 0 0 1 489 O ₇ oil CL002 -0.05 0 0 0 0 0 0 490 0 _? 002 0,002 > Ο, Ο5 0 0 0 0 0 0 491 0 ^ 005 0 ^ 03 > 0.05 0 0 0 0 0 0 492 0 ^ 003 0,002 ^) ₁ OS 0 0 0 0 0 0 493 0.005 O ₁ OOS > \ ⁰⁵ 0 0 0 0 0 1 494 O ₁ oil 0. ₍ 005 -P ₁ 05 0 0 0 0 0 0 495 O ₁ oil 0,002 ^ 05 0 0 0 0 0 0 496 0 ^ 003 0.001 ^ 05 0 · 0 0 0 O * 0 0 497 0.001 0 ^ 002 12:01 0 0 0 0 0 0 498 0 ^ 0008 0 ^ 005 O ₇ 03 0 0 0 0 0 0 499 0 ^ 002 0,002 O ₁ 01 0 0 0 0 0 0 500 , 0,003 0,002 0) 05 0 0 0 0 0 0 501 0,002 0,002 0.03 0 0 0 0 0 0 ) Ί ι 502 0 003 0 ^ 002 >), 05 0 0 0 0 0 0 503 0,002 O ₁ OOl ^ 05 0 0 0 0 0 0 504 0.005 0,002 -0.05 0 0 0 0 0 0 505 0008 0.001 > 0.05 0 0 0 0 0 0 506 0.002: > 0 _η 003 12:01 0 0 0 0 0 0

- 243 -

2197 43 -243-

Table II

indu ing Lepidopteri: CL cides Baui Phytotoxic effect mwollc pumpkin 2 hl 1 2 Wi £ k_ung_ 0.005 _. · 0 0 0 0 SMC 0 002 TBW 1.2 1 0 0 0 0 507 0,002 0,002 > 0.05 0 0 0 0 0 0 508 0.001 0001 0 _f 03 0 0 0 ο 0 0 509 0001 0005 _0r 05 0 0 0 0 0 0 510 0.005 0 005 > 0.05, 0 0 1 0 0 1 511 0001 Oj 005 > ° 1 ⁰⁵ 0 0 1 0 0 1 512 O ₁ OOl 0 _f 006 0.05 0 0 0 0 0 0 513 0,002 0,002 > O, O5 0 0 0 0 0 0 514 O ₁ 005 0005 > Q, 05 0 0 0 0 0 0 515 0 002 0002 0.05 0 0 1 0 0 1 516 0-001 0 _? 005 ^ 05 0 0 0 0 0 1 517 0002 0 ^ 005 > Q, 05 0 0 0 0 0 0 518 0,003 0005 > 0.05 0 0 0 0 0 0 519 0001 0 _} 003 > 0.05 0 0 0 0 0 0 520 Oj 001 0,003 ^ 05 0 0 0 0 0 0 521 0008 0.005 > Q, 05 0 0 0 0 0 0 522 0005 0.0002 ^ 05 0 0 0 0 0 0 523 0.005 O ₇ OOl > 0, Ο5 0 0 0 0 0 0 524 Oj 002 0.0005 > 0.05 0 0 0 0 0 0 525 0,002 0.0003  > Q.O5 0 0 0 0 0 0 526 0,002 0-0002 > Q) 05 0 0 1 0 1 3 527 0,002 > 0-05 0 0 528 0002 12:05 0 0

- 244 -

219 7 43 - 244 '

SMC CL TBW Table II 1 2 1.2 1 2 O ₁ 002 0.0002 > \ 05 0 0 0 0 0 0j002 OyOOl ^ 05 0 0 0 0 0 0 _; 002 o _t ooi >), 05 0 0 0 0 0 Compound Lepidoptericides No. Effect 0.001 0 ^ 0002 0.05 0 0 0 0 2 O ₁ 002 o / oooi <PjO5 0 0 0 0 0 529 0 ^ 002 0j002 12:05 Phytotoxic effect of cotton pumpkin 0 0 0 0 0 530 0.002 * * 0-0002 ^ 05 1.2 0 0 0 0 0 531 0 _} 002 0.0005 >, 05 0 0 0 0 0 0 532 O ₁ OOl 0 _; 0005 0.05 / 0 0 0 0 0 0 533 0,002 Oj 002 OJ 05 0 0 0 0 0 0 534 0001 0 _; 0005 0 _t 05 0 0 0 0 0 0 535 0,002 O ₇ OOOl 0.05 0 0 0 0 0 0 536 0.0002 OfOOl 12:05 0 0 0 0 0 0 537 0.03 0002 OJ 05 0 0 0 0 0 0 538 O ₁ OOOS 0.0003 <φ.Ο5 0 0 0 0 0 0 539 0,002 0.0001 OJ 05 0 0 0 0 0 0 540 0.03 Oj.002 OJ 05 ο 0 0 0 0 0 541 0001 OyOOOl OJ 05 0 0 0 0 0 0 542 0.0005 / 0 _r 0005 OJ 05 0 0 1 0 0 3 543 Oj 001 0.0003 <P, 05 0 0 1 0 0 1 544 O ₁ 002 0.0002 0.05 0 0 0 0 0 0 545 0,002 O ₁ 0002 0.05 0 0 0 0 0 0 546 0 547 0 548 0 549 0 550 0 0 0

- 245 -

21 9 7 43 CL TBW -245- 1 2 1.2 1 2 0,001 0 05 Table II 0 1 0 0 1 Connector no. ig Lepidoptericidal effect 0 _t 0002 0 05 0 0 0 0 1 SMC 0 0003O ₁ OS 0 0 0 0 1 551 OjO3 0.0003 O ₁ OS 0 0 0 0 0 552 Oj0003 O ₁ OOOS ^ o ₁ Os 0 0 0 0 0 553 Oj 001 O ₁ OOOl <p.O5 0 0 0 0 1 554 O ₁ OOl 0 ^ 0002 O ₁ OS 0 0 0 0 2 555 ι 0.002 0,0003 <p, 05 0 0 0 0 0 556 0 ^ 005 0 ^ 02 0.05 0 1 0 0 1 557 O ₁ OOOs 0 ^ 02> 3, O5 0 0 0 0 1 558 Oj0002 0 ^ 02 Oj 03 1 3 0 1 5 559 0 ^ 003 O ₁ OOl 0 05 Phytotoxic effect of cotton pumpkin 0 2 0 0 2 560 0,003 0 ^ 003 O ₁ OS ..1 / 2 0 0 0 0 0 561 0 ^ 001 0,0005>), 05 0 0 2 0 r-l 3 562 0 ^ 001 O ₁ OOOS>). O5 0 1 2 0 1 2 563 O ₁ OOl O ₁ OOOS ο, Ο5 0 0 2 0 1 3 564 0003 O ₁ OOOS 0 ^ 05 0 0 2 0 i-l 2 565 0 _} 002 0.0002 ^ 05 0 0 1 0 1 2 566 O ₁ OOOs 0 ^ 003 0 ^ 02 0 0 0 0 0 1 567 O ₁ 0003 0 _} 0003 0 05 0 0 1 0 0 1 568 0 | 0003 O ₁ 0003>) _f 05 0 0 2 0 r-l 2 569 0 ^ 0008 0.0002 O ₄ 05 0 0 2 0 1 3 570 0 ^ 0003 0 571 O ₁ OOOs 0 572 0.0002 0 0 0 0 0 0 0 0 0 0 0

2197

Table II

Compound lepidoptericidal

Mr. effect

SMC

CL TBW

573 0-001 0-0005> λΟ5

574 0 001 0 0005> P.O5

575 OjOl 0.0008>>. 05

576 0.0002 0.0005> P.O5

577 0 ^ 002 0.0003 0.05

578 0.0005 0 ^ 005 ^ -05

579 0.0005 0 0005> Q.O5

580 0 0005 0.0008 ».05

581 0.0002 0.0005 a05

582 0.0002 0.0005 0.005

583 O ₁ 0003 0.0003

584 0.002 0.001 0.05

585 O ₁ 003 0.002 α 05

586 0 ^ 3 0.005 0.05

587 O ₁ Ol 0 ^ 002 αΟ5

588 ^ 0 ^ 05 ο, Ο5 QjO5

589>). Ο5 0 008 α 05

590 ο., 05 0.002 Χ05

591 O ₁ OS O ₁ oil 0.05

592 0.01 ο, ΟΙ

593 0 ^ 03 O ₁ oil XL 05

594 0 ^ 005 0 ^ 002 0 ^ 05

Phytotoxic effect of cotton pumpkin .

1.2

1/2 1 2

0 0 1 0 12

0 0 2 0 12

0 0 1 0 1 2

0 0 10 0 2

0 0 1 0 0 2

0 0 1 0 0 2

0 0 0 0 12

0 0 0 0 0 1

0 0 0 0 0 1

0 0 1 0 0 2

0 0 1 0 0 2

0 0 0 0 0 0

0 0 0 0 0 0

0 0 1 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 13 0 1 2

0 0 1 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

- 247 -

SMC CL cides -247- 1 2 1.2 1 2 > 0} 05 0.002 0.005 0 002 TBW Table II 0 0 0 0 0 0 0 0 0 0 21 < 0 005 0 ^ 005 0.05 0.04 0 0 0 0 1 0 ^ 005 12:01 12:05 0 0 0 0 1 P743 O ₁ OOl 0 0002 > 0 _? 05 0 0 0 0 1 <0 001 0.0005 0j02 0 0 0 0 0 Compound Lepidopteri no effect <B ^ 001 0 ^ 0003 0 _} 04 0 1 0 0 1 0 ^ 002 0003 0005 1 2 0 1 2 595,596 0002 0.0003 * .O5 0 0 0 0 1 597 I 0 003 O ₁ 003 0.08) 0 1 0 0 1 598 0 003 O ₁ OS 12:05 0 0 0 0 0 599 0.4 59.05 0 0 0 0 0 600 0 ^ 05 ".05 Phytotoxic effect Cotton gourd 0 0 0 0 0 601 ^ 05 0.2 > a05 1.2 0 0 0 0 0 602 0 ^ 003 0.002 0.0003 0 ^ 0005 > αθ5 0 0 0 0 1 2 0 0 0 0 1 1 603 0008 0.0002 α.05 ι ^ 05 0 0 1 0 0 1 604 0002 0 ^ 001 ^ 05 0 0 1 0 0 1 605 0,003 0001 ".05 0 0 1 0 0 1 606 0 ^ 01 O ₁ OOl 0 ^ 003 0 002 12:05 0 0 0 1 2 0 0 0 0 1 2 607 0 * 004 <P.001 ».05 0.04 0 0. 1 0 0 2 - 248 608 ^ 05 0 609 610 0 611 0 612 0 613 0 614 615 0 616 0 0 0 0 0 0 0 0 0

2197 43

Table II

SMC CL TBW

617 0 ^ 003 α _; 01 0.05

618 Q ^ OOl αΟΟ5 0.05

619 Qj002 O ₁ 005 0.05

620 0 _T 002 0.002> 0j05

621 O ₁ Ol 0 ^ 003 0.05

622 0 ^ 03 o ^ OOl> 0 ^ 05

623 0.002 o.Ol ^ 05

624 0 ^ 001 0,0008 0.03

625 0 ^ 003 o ^ OOl 0.05

626 0.003

12:03

627 0.005 0.001 0.01

ι ι 7

628 0,003 o.OOl ».05

629 0,001 o, OOO5 20,05

630 0.003 <t 001 0.05

631> 0,05 o.Ol », 05

632 0 ^ 005 0.02 / 0. ₍ 05

633 0 ^ 01 0.01 0.1

634 0.002 0.003 0 _r 05

635 0.008 ö.002> 0.05

636> o, 05 0,1 0 ^ 05

637 0,002 0 ^ 003> P, 05

638 0.003 0 _? 003 ^ P, 05

1/2 1 2 1/2 1 2

0 0 1 0 0 2

0 0 2 0 0 1

0 0 10 0 2

0 0 10 0 1

0 0 0 0 0 0

O 0 1 0 0 1

0 0 1 0 0 1

0 0 0 0 0 1

0 0 0 0 0 0

0 0 1 0 0 1

0 0 1 0 0 1

0 0 0 0 0 0

0 0 0 0 0 0

0 12 0 12

0 0 1 0 0 1

0 0 1 0 12

0 0 1 0 0 0

1 2 4 12 3 0 0 1 0 0 1 0 0 0 0 0 0 0 13 0 14 0 13 0 2 4

- 249

2197 43 -249-

Table II

Compound Lepidoptericides' Phytotoxic Effect

Mr-. __ effect cotton Kurbis_

1/2 12 1/2 1 2

0 Ό 0 0 0 0

0 12 0 13

0 0 0 0 12

0 0 0 0 0 0

0 0 1 1 2 3

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 12 0 13

0 0 0 0 0 0

0 0 0 0 0 0

0 12 0 13

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

0 0 0 0 0 0

- 250. -

SMC CL TBW 639 > 0.05 Q ₇ I > 0 _} 05 640 0 _? 008 0 ^ 05 > Ρ, 05 641 ^ 05 ° ι ¹⁵ > 0:05 642 >) _? 05 0.2 ^ .05 643 0,003 0.03 ^ 05 644 0.01 ^ 05 ^ 05 645 0.01 > Ο, 05 >), 05 646 0.03 12:05 >) _R 05 647 0.03 ^ 05 ^; 05 648 0.01 > 0.05 >), 05 649 0,003 ^, 05 > 05 650 0,003 0,003 >, 05 651 0.05 0.03 ^ ° 5 652 °, 05 0.03 > ₇ Ο5 653 0 ^ 002 0.002 ι <0.05 654 > 0.05 0.4 >), 05 655 ^ 05 ⁰ I ² ^, 05 656 ^ 05 ο, Ι > 0.05 657 0.05 > Ο, Ο5 658 0.03 >), 05 >, 05 659 > 0.05 0.05 12:03 660 >), 05 0.03 >) ⁰⁵

-250-Table II

Compound Lepidoptericides No. Effect

Phytotoxic ^ effect cotton pumpkin

661 662 663

667 668

SMC CL

12:03

o.öl

TBW ) .O5

05 v> 0 05 » _r 05

Oj 002 0 005

664 <0 ₎ 001 0 ^ 002

665 <p.001 0 005 Q. 05

666 <0.001 0.001> o, O5

> 0.05 X) ₅ OS> Q, 05

12:03

0.1 /

669 0.002 0.002 005

670 0.03 0.05> aO5

671 0., 0Ol <P 001 Q ₁ 05

672>). 05> 0.05> o, 05

673 ^ o, 05 0.5> a05

674> 05> 05> Q, 05

675 0.05> o.05> Q, 05 676

0.2

677 >>, 05

678>). ₍ 05

679 a 003 0.003

680 0 ^ 002 0 ^ 002> Q, 05

681> 0.05 αϊ> 0.05

682> ^ 05> 0.05> Q, 05

1/2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

3 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 1 0 0

5 0 1 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 1 2 0 0

1.2

1 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0

'4 0 1 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 1 0 0

-

219743 -251-

Table II

Compound Lepidopteric phytotoxic effect

No effect cotton pumpkin

SMC CL > Q, 05 >, 05 TBW 683 > 0.05 0.1 > 0.05 684 > ⁰⁵ 0.15 >} 05 685 > 0 _f 05 ^, 05 > αθ5 686 »05- >> 05 > O, O5 687 0.03 O ₁ 003 ^ 05 688 cy 01 0.03 > .05 689 > 0.05 > O, O5 690 0,008 O ₇ 002 >} 05 691 0,008 0,008 ^ 05 692 0 ^ 03 0.03 > 0 _f 05 693 0.0003 Oj 002 694 0,002 0.005 a 03 695 O ₁ 0005 0.0008 0.03 696 >) _; 05 0.03 ^ 05 697 >) _R 05 0.03 ^ 05 698 > 0.05 0.12 _{> 0f} 05 699 0 _f 008 0 ^ 3 _{> 0} , 05 700 > 0.05 0.4 ^ 05 701 0.4 > 0 _f 05 702 _0r 005 0.03. > 0.05 703 0,002 0.001 > 0.05 704 > 3 _r O5

1.2 1 2 ul 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r-l 0 0 1 0 1 2 0 1 2 0 0 0 0 1 2 0 0 O 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 r-l 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -2 52 0

Table II

, , · Phytotoxic effect

Compound lepidopteric cotton gourd

_{Nr #} Effect == -

SMC CL TBW i / 2 12 1/2 1 2

705 0 _; 001 0.0008 0 05 0 0 0 0 0 0

706 0.01 0 005>) O5 0 0 0 0 0 0

707 OjOOl 0 ^ 03 ^ 05 0 0 0 0 0.1

708 0,0003 0 ^ 001> 0.05 0 0 0 0 0 0

709 0.003 O ₁ OOe> o _r 05 0 0 0 0 0 0

710 0.005 0j005> 0 _f 05 0 0 0 0 0 0

711 QjO3 0,03>) _f 05 0 0 0 0 0 0

712 O ₁ 001 0.002> o. 05 0 0 0 0 0 0

713 0.002 0.002> o. 05 0 0 0 0 0 0

714 Qj008 0 003> D.O5 0 0 0 0 0 0

715 O ₁ OOOS 0 003> a, 05 0 0 0 0 0 0

716> 0.05>> .05> 0.05 0 0 0 0 0 1

717 O ₁ OOS 0.003> 0.05 0 0 0 0 0 1

718 0.001 0.0005 o _f O3 0 0 0 0 0 0

719 0 002 O ₁ OOl <b, 05 0 0 0 0 0 0

720 0.002 0 _f 003 <q _? 05 0 0 0 0 0 1

721 O ₁ 002 O ₁ 01 <ij 05 0 0 0 0 0 0

722 0.001 0.005 O ₁ I 0 0 0 0 0 0

723> 0 ^ 05> ^ 05 ^ O ₁ 05 0 0 0 0 0 0

724 0 _r 002 0,01 0,05 0 0 0 0 0 0

725 0,002 0.03 », 05 0 0 0 0 0 0

726 O ₁ OOOS 0 _f 0008 0-04 0 0 0 0 0 0

'- 253 -

9743 SMC CL 0 _f 03 0 01 TBW -253- 1 2 1.2 ~ 1 2 0 ^ 03 12:03 0 _? 05 Table II 0 0 0 0 0 2 1 o _T ooi OjQt) I 0 05 0 0 0 0 0 Compound Lepidoptericides No. Effect 0.05 >) _; 05 o _; oi 0 0 0 0 0 o: 0005 o _; 0005 "05 0 0 0 0 0 727 > 5 ° >) _; 05 0 0 0 0 0 728 »7 05 >), 05 ^ 05 0 0 0 0 0 729 > _f 003 0 _; 12 > AO5 0 0 0 0 1 730 O ₁ oil 0008 Qj 05 0 0 0 0 0 731 "05 o _; 4 0.1 0 0 0 0 0 732 0 ^ 01 ^ 05 5O ₁ I 0 0 0 1 2 733 XL 05 ⁰ I ² 0 0 0 0 0 734 ^ 05 ^ 05 Oy 04 Phytotoxic effect of cotton pumpkin 0 1 0 O- 1 2 735 > ajO5 O ₇ I 12:05 1.2 0 1 0 0 1 736 > 0j05 0 ^ 03 _0r 04 0 0 0 0 1 2 737 0 _T 03 12:04 0 0 0 0 0 0 738 OJ 05 0 _; 005 0 ^ 05 0 0 0 0 0 0 739 "05 O ₁ I 12:04 0 0 0 0 0 0 740 > Α, 05 0 _f 05 > 0:05 0 0 0 0 1 2 741 0.005 0 _t 005 O ₁ 05 0 0 0 0 1 2 742 α 003 0.0005 _0r 04 0 0 0 0 0 0 743 J ¹ , 0 05 0 0 0 0 0 0 744 0 _f 05 O ₁ I 0 745 > 0 _t 05 0 0 0 0 0 0 746 0 - 25: 3 - 747 0 0 748 0 0 0 0 0 0 0 0 0

219743

Table II

Compound lepidoptericidal Mr VJirkuna 749 SMC CL Oj 005 TBW Baui Phytotoxic effect mv ^ li «pumpkin 2 hl 1 2 IN -L · 750 ^ 05 > 0 _? 05 X} 05 1.2 1 0 0 0 0 751 03 <0j001 Xl 05 0 0 0 0 0 0 752 Ck 005 OJ 008 0.05 0 0 0 0 0 0 753 cyanuric chloride 0 _; 05 > ^ 05 0 0 0 0 0 2 754 CkO3 OjO3 > A, 05 0 0 0 0 0 0 755 Ck 005 0.05 / * lo5 0 0 0 0 0 1 756 Ck ₁ 003 03. > 0jO5 0 0 0 0 0 1 757 OJ 008 0.03 / O ₇ 05 0 0 0 0 0 1 758 03 03 0.05 0 0 0 0 1 2 759, 0j008 0.15 OjO5 0 0 0 0 0 2 760 0.01 OjOl X. 05 l 0 0 0 0 0 0 761 Oj 006 0.5 0 _; 05 0 0 0 0 0 0 762 "J05 12:01 "JO5 0 0 0 0 0 0 763 0j05 I 0.05 XJ ₇ 05 0 0 0 0 0 0 764 12:05 I 0.03 >) JO5 0 0 0 0 0 0 765 "J05 0 _f 05 0 _f 05 0 0 0 0 0 0 766 ".05 > ₇ O5 » _T 05 0 0 0 0 0 0 767 "JO5 OjOl _0r 05 0 0 0 0 0 0 768 > 0j05 0.05 "05 0 0 0 0 0 0 769 12:05 I ^ 05 ο 0 0 0 0 0 770 ^ j 05 <a > 0.05 0 0 0 0 0 0 ^ 05 > ^ 05 0 0 0 0 0 0 J 0 0 - 2 55

2197 43

Table II

Compound lepidoptericidal phytotoxic effect

No effect cotton pumpkin

SMC CL TBW

771 0,01 O ₅ I ^ 05

772 0 ^ 003 0.005 0 ^ 05

773 O ₇ Ol 0 ^ 005 ^ 05

774 o, OOO5o.OOO8 QOl

775 0.0003 0.0004 0.003

776 0.0005 0.001 Q05

777 0 ^ 003 O ₁ OOS X ₇ 05 '

778 0.0003 O ₇ 0003 a 05

Symbols of Table II

SMC:

, Kohlweissling looper

TBW: tobacco caterpillar ^>: greater than: less than

1.2 1 2 ul 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 1 0 0 2 0 0 1 0 0 1 0 1 3 0 1 2 0 0 1 · 0 0 1

19 7

- 256 biocidal test series

In vitro test series

Test tubes with sterilized food and Maize extract soup were prepared. Aliquots of the poison, dissolved in a suitable solvent, were added to the soup through the stopper, with 50 ppm concentrations down. The organisms studied consisted of a fungus, Botrytus cinerea, and a bacterium, Staphylococcus aureus (S.a.) Roseenbach.

3 drops of a spore suspension of the fungus were introduced into test tubes with malt soup and 3 drops of the bacteria in test tubes with food soup. One week later the growth of each organism was observed and the effect of the tested compound was recorded as the lowest concentration in ppm at which a 100% Prevention of growth with respect to untreated test glasses was obtained. The Reslutate are summarized in Table III.

Fungicidal test series

Preventive foliage sprays flour dust

The compounds to be tested were dissolved in a suitable solvent and diluted with water containing a few drops of a wetting agent. The concentrations to be tested were down from 1000 ppm. The solutions were sprayed until dripping onto the primary leaves of pinto beans (Phaseolus vulgaris L.). After the plants were dry, the leaves were dusted with spores of the mildew fungus (Erysiphe polygoni de Candolle). The plants were kept in a greenhouse until fungus growth on the leaf surfaces occurred. The effect was recorded as the lowest concentration in ppm at which a 75% or greater reduction with

- 257 -

219743 .__ "" _

cyst growth on the leaf surface with respect to non-treated but fungus-infested plants. The results are summarized in Table III.

Table III 155 biocides Botyrytus connection 166 LC-IOO (ppm) cinerea No. 170 Staphylococcus 175 aureus - 183 - - 213 4M - 309 - (10) 310 - 662 5 10 733 10 5 769 25 10 - - 25 - _m

Fungicides LC-75-100 (ppm) mildew

500 500 500 1000 500 500 500

500 500

(). = partial control - 50% or greater

The primary concentrations indicated above, were selected only from points which ensured a good course of the trials and none of the specified values in the tables should wherein a Lepidoptere effect can be determined to be the highest possible Bet _7, are considered.

The compounds of the invention are generally used in

- 258

219743

suitable compositions which can be applied well. In general, such compositions contain inert or active components or diluents or carriers in addition to the active compound. Examples of such components or carriers are organic solvents such as sesamoel, xylene range solvents, and long chain petroleum fractions; Water;' Emulsifier; surfactants; Lime; pyrophyllite; diatomite; Plaster; clays; and propellants such as dichlorodifluoromethane.

The active compounds may further be mixed with dust carriers for application as powders, with granular carriers for application with fertilizer spreaders, or with soil or air mills. The compounds may also be mixed into wettable powders or emulsifiable concentrates or with solvent and surfactant for application as sprays, aerosols or emulsions. The connections bezw. the compositions of the invention may be applied at any location which is infested with lepidopterans. Examples of such places are insects, dwellings, clothes, plant surface and soil. If desired, the active compositions may be applied directly to organic matter, seeds or foodstuffs in general from which the insects feed _/ or applied directly to the insects. If the compositions are to be applied in this manner, nonvolatile compositions may be selected.

Particularly preferred compositions are those which contain an insecticidal amount of the active compound together with an inert, insoluble solid carrier. Examples of such compositions are wettable powders, dust compositions, free-flowing compositions in which the solid carrier is in finely divided form; granular compositions in which the solid carrier is in granular form.

- 259 -

219743

The isothiourea compounds of the invention may also be incorporated into baits from which the lepidopteran larvae like to feed so that the isothioureas of the invention are more rapidly ingested by the larvae. Effective baits are cottonseed meal, cottonseed oil, cottonseed extracts, sucrose, sugar, citrus fruit, molasses, soybean oil, soybean meal, corn oil, corn kernel extracts, corn seed extracts, mixtures of these with suitable emulsifying agents and wetting agents.

The amount of active compound in the composition is such that upon application of the composition at the place of residence or the foods of the insects, a substantial portion of the insects is destroyed or at least seriously injured. The active compounds of the invention may be used either alone, as a single pesticidal component, or in admixture with other known pesticidal compounds. The pesticidal compositions of the present invention need not be active themselves as such. It suffices if the compositions have their effect by external influences, such as light, or by physiological changes which are obtained when taking the compositions into the body of the insects.

Those skilled in the art will appreciate the use of the insecticides of the invention. In general, the insecticides are used as a component of a liquid composition, e.g. an emulsion, a suspension or an aerosol spray. The concentration of the insecticidal component in the compositions can vary widely, generally the composition will contain no more than about 50% by weight of the active compound.

- 260 -

Claims (10)

Claim: wherein R and R are selected from the group consisting of: C ₂ -C ₁₀ alkyl, C "2 - C," alkoxyalkyl, and Phenyl and R and R. together have 12 to 22 carbon atoms. R ~ is selected from the group consisting of C ₁ -C ₁₄ alkyl, ^C 3 ~ ^C 10 ^Alkenv1 '
C ₃ -C ₄ alkynyl, C ₂ -C ₄ hydroxyalkyl
C ₂ -C ₆ alkylthioalkyl,
C ₉ - Cr alkyloxyalkyl, (CH ₂ ) _n [X (CH ₂ ) _n ] _y X is 0 or S and y = 1-4, ti - (CH ₂ ) _Q COH where η = 1-10, Phenyl, and
, Phenethyl.
where Ro is selected from the group consisting of: 219 7 43 -ibt- Carboalkoxyalkyl wherein the alkyl is a C 1 -C ₄ alkyl, alkylketoalkyl wherein the alkyl is a C 1 -C ₄ alkyl, hydroxyalkenyl wherein the alkenyl is a C ₃ -C ₄ alkenyl, hydroxyalkyl wherein the alkyl is a C ₁ - C ₁₂ alkyl, \ Formyl hydroxymethyl, Hydroxyhaloethyl wherein halo is chloro, bromo or iodo, substituted phenoxyalkyl wherein the alkyl is C 1 -C ₂ alkyl and the substituents are p-methoxy, Cl, NO ₃ or CN, where R is selected from the group consisting of: -OH, -NH- or
C, -C ₄ alkoxy, OH OH j 2
-CH- ^ HN-C = NR ₁ Have definition » wherein R, R, and R ₂ are as indicated above where R, R, and R2 are those given above Have definition; OH -PO ₃ * B, -PO ₂ - or -SO ₃ -B where B is a base. 2197  8 A CN wherein R _{4 is} selected from the Group consisting of: C ₁ -C ₂₂ alkyl, Hydroxyathyl, naphthyl, phenyl, substituted phenyl wherein the substituents are independently selected from the group consisting of halogen, Cn-C ₅ alkyl, C, -C ₅ alkoxy, nitro, cyano and CH 3 g NHCN-C = NR ₁ 1 J 1 R have a given definition, II - (CH ₂ J) ₆ NHCN-C-NR ₁ R have a given definition, where R, R, and the above where R, R, and the above-mentioned ο SR ₂ ίο * 3 where R, R, and R "have the definition given above, 0 ^ / Jy- CH ₂ - ^) - NHCN-C-NR ₁ have a given definition, where R, R, and R "are the obori 2 1 yen / O f 2 NHCN-C = NR ₁ R -4 * 3- -ύ- where R, R, and R _{0 are} those given above Have definition, qtj 0 p2 NHC-N-C 0 0 \ I » " n / A NRi NHC-O (CH ₉ CH ₀ ) O-CNH-Z'VS 'V ^CH 3 Ch7 where χ is 1 to 8 and R, R and R are as defined above, 0 SR ₀ Il I ² ₀ NHC-NC Z'm * '**' - ⁱ "- ^ir \ / NRt where m is 2 or 3 and R, R and R ₂ are as defined above, where R, R, and R »have the definition given above, where R, R ₁ and R ₀ are as defined above, 197 wherein X is selected from the group consisting of NH and Y is hydrogen or methyl, and R- is selected from the group consisting of: C ₁ -C ₁₈ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, Cp-C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl, C ₇ -C ₃₀ polycycloalkyl, C *) - C-, ε-polyoxyalkoxy-L, C -C ₆ hydroxyalkyl, C ₃ -C ₁₀ alkoxyalkyl, C ₃ -Cg carboalkoxyalkyl, C ₄ -C ₈ cycloalkylalkyl, C ₄ -C ₈ alkylcycloalkyl, C ₄ -C ₇ cycloalkylimino, C 1 -C ₈ , _o- alkylimino, C, -C ₃ alkylamino, C.-C, ρ dialkylaminoalkyl, Cg-C ₁₀ cycloalkenyl, phenyl, Akylphenyl wherein the alkyl is a C ..- C ₄ alkyl, 219743 - I <o5- Parachloroalkylphenyl wherein the Axkyl is a C ₁ -C ₄ alkyl, naphthyl, anthracenyl, Benzamidocycloalkyl where the alkyl is a C ₁ -C ₂ alkyl, Pyranylmethyl, tetrahydrofurfuryl, thiophenmethyl, benzhydryl, halobenzhydryl, polycyclic alcohol, and substituted phenyl wherein the substituents are selected are made up of the group: C ₁ -C ₄ alkyl, halogen, nitro, Trifluoromethyl, formyl, Chloroacetyl, C ₁ -C ₄ alkoxy, hydrogen, benzyl, Chlorobenzyl, phenethyl and substituted phenethyl wherein the substituents are selected from the group consisting of: C, -C ₄ alkyl and Halogen, and R ,, is selected from the group consisting out : C ₁ -C ₄ alkyl, Ct-C, alkoxyalkyl, and C ₃ -C ₄ alkenyl. R ^ O and RQ together form heterocyclic compounds, under the condition that fals X = 0 or SR _1n no
Is hydrogen / and substituted phenyl wherein the substituents are selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, Phenoxy, _ V _ 219 '266 - Trifluoromethyl, C ₁ -C ₆ thioalkyl, nitro, Isocyanato, C ₂ ^- C ₄ polyalkoxy, C ₃ -C ₇ cycloalkyl, ^C 3 ~ ^C 24 carboalkoxyalkyl, C ₁ -CG haloalkyl, C ₃ -C ₁₂ alkenyl, C ₂ -C ₆ Dialkylami.no, phenylamino, C ₁ - C ₂₄ alkyl, ^C 3 ~ ^c l2 Hydroxyalkylamidoalkyl, ^C 5 ~ io ^{c N / N} ~ ^H y ^dro isocyanatoalkyl wherein the alkyl is a C, -CrAlkyl, C ₃ -C ₁₂ alkylamidoalkyl, Polyalkoxyamido-alkyl wherein the polyalkoxy unit between 3 and 6 repeating, C _? -C3 alkoxy units and the amidoalkyl moiety has between 4 to 12 carbon atoms having , -SO ₂ Cl, -SO-, polyalkoxy-amidoalkyl wherein the polyalkoxy moiety 3-6 C ₂ -C, alkoxy units and the amidoalkyl moiety has 4-12 carbon atoms. Rr is selected from the group consisting of: Hydrogen, C ₁ -C ₄ alkyl, C ₃ -C, alkoxyalkyl, C ₃ -C ₄ alkenyl, hydroxyethyl and phenyl. R ₄ and R _r together form heterocyclic compounds, and ti 6 wherein X is 0 or S, η is 0 or 1, and R _{β is} selected from the group consisting of: 219 CJC ₁₈ alkyl, C ₅ -C ₆ haloalkyl, phenyl, and substituted phenyl wherein if η = 1, the substituents be selected from the group consisting of: Nitro, chloro, C ₁ -C ₂ alkyl, C ₄ -C ₆ polyalkoxyalkyl C ₃ -Cg cycloalkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₆ alkoxyalkyl, C ₂ -C 8 hydroxyalkyl, C ₁ -C ₃ carboxyalkyl, and Cc-Cg trialkylammonium alkyl salts, and if η = 0, the substituents are selected the group consisting of: Chlorine, thiokalium, Ci-C ₁ O alkyl, benzyl, C ₁ -C ₂ heteroalkyl, C ₃ -C ₄ chloro-carboxyalkyl, C ₄ -Cg polyalkoxyalkyl, and acetyl. OO | i I 'wherein R _{n is} selected from the group consisting -CR ₇ CY _H Z ' ^α from: - (CH ₉ -) -, ^{A u} where η = 0 or 8, -CH = CH-, where MH or Cl is, 19 7 -CCl-CCl-, ^and -CH ₂ OCH ₂ -, -OCH ₂ CH ₂ O-; d = 0 or 1 if d = Y selected from the group consisting of: -S, and Z is selected from the group consisting of: -C ₁ -C ₁₈ alkyl, hydrogen, C.-Cj, polyalkoxyalkyl, C ₄ -Co dialkylaminoalkyl, C -, - C 5 alkynyl, Phenyl,. Substituted phenyl, organic salts, inorganic salts, and at * " d = 0, Z, Cl or I is 1, wherein R, R ₁ and R _{0 are} the above-mentioned R 1 ^ Have definition. 2 8 wherein Rq is selected from the group consisting of: C, -C-, ₀ alkoxy, amino, C -, - C -, _n alkoxyamino, hydroxy and
organic base. 219743 where w = 0-2 and R _{g is} selected the group consisting of: Amino, C ₁ -C ₁₀ alkyl, C ₁ -C ₄ haloalkyl, phenyl, C ₁ -C ₁₀ dialkylamino, C -, - C-, _n- alkylamino, CJC ₁₀ -alkoxy, substituted phenyl wherein the substituents are selected from the group consisting of: nitro,
chloro, C ₁ -C ₄ alkyl, and methoxy. 2. Composition according to item 1, characterized in that in the active compound R and R are independently selected from the group consisting of C ₅ -C ₉ alkyl,
Cc-Cq alkoxyalkyl, and
Phenyl and Have R and R ₁ together 12 to 22 carbon atoms wherein ·. R _{2 is} selected from the group consisting of: C ₁ -C ₆ alkyl,
C3-C5 alkenyl,
C ₃ -C ₄ alkynyl,
C ₃ -C ₃ hydroxyalkyl,
^C 2 ~ ^C 4 alkylthioalkyl,
C ₂ -C, alkyloxyalkyl ) J ₁ ] y where η = 1 or 2, X is 0 or S and y = 1-2, 11 - (CH ₂ ) _n C0H where η = 1-5, Phenyl and phenethyl. 197 3. Composition according to item 1, characterized in that in the active compound R and R, are independently selected from the group consisting of: Cg-C ₈ alkyl, and C _ß -Cg alkoxyalkyl, and ' Phenyl and R and R ₁ together have 12 to 22 carbon atoms. wherein R "is selected from the group consisting of: C ₁ -C ₁₃ alkyl, C ₃ -C ₃ alkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₃ hydroxyalkyl, C ₂ -C ₄ alkylthioalkyl, C ₃ -C ₄ alkyloxyalkyl (CH ₂ ) [X (CH ₂ )] y * " ^{Δ n} where η = 1 or 2, X is 0 or S and y = 1-2, 0 M - (CH ₂ ) _n COH where η = 1-3, Phenyl and phenethyl. 4. Composition according to item 1, characterized in that Ro is selected from Carboalkoxyalkyl wherein the alkyl is a C ₁ -C 6 alkyl, alkylketoalkyl wherein the alkyl is a C ₁ -C ₃ alkyl, hydroxyalkenyl wherein the alkenyl is a C ₁ -C 4 alkyl, hydroxyalkyl wherein the alkyl is a C ₁ -C, Is alkyl, formyl hydroxymethyl, Hydroxyhaloathyl wherein the halo is chlorine or bromine, substituted phenoxyalkyl wherein the alkyl is a C, alkyl and the substituents are p-methoxy, Cl, NO ₃ or CN, 219743 7 ON "Λ ¹ in which Methoxy is, or OH OH f -CH-CHN-C = NR ₁ L where R, R, and R "are those given above Have definition where R, R ₁ and R »have the definition given above, OH Β, -PO ₂ * B or -SO ₃ - • CN \ wherein B represents an organic base; wherein R _{4 is} selected from the group consisting of: C ₁ -C ₁₂ alkyl,
Hydroxyethyl,
naphthyl,
phenyl, substituted phenyl wherein the substituents are independently selected from the group consisting of; Halogen,
CJC ₂ alkyl, ^C i ~ ^C 2 alkoxy, nitro, cyano and -CF _3, 197 - in - - where R / R- and R _{0 have} the definition given above, - (CH ₂ ) where R, R ₁ and R _{0 have} the definition given above, where R, R and R ₀ are as defined above, 0? ^R 2 CN-C = NR ₁ ™ * i ! CN-C = NR ₁ SR. where R, R, and R _{0 have} the definition given above, NHC-O (CH ₉ CH ₉ O) ^ - C CH, where R, R, and R "have the definition given above, NHC-N-C = NR- where χ is 1 to 8 and R, R ₁ and R2 have the definition given above. _ Vi _ 2197 43 NHC NH ' S-N- C = NR ₁ NHCCH ₉ ) ^ - NHC ^{2 m 2 m} / \\
s = J> CH ₃ CH, where ir is 2 or 3 and R, R, and R have the definition given above 0 ^SR 2 ι * NHC-N-C = NRi wherein R, R, and R2 are as defined above, SR ₉ Ο Ι - O / NHC-NC = NR ₁ NHCNH - (^) R CHO where R, Ri and R _? have the definition given above. NHCXR 10 where X is selected from the group consisting of: 11 Y represents hydrogen methyl, and R "Lq is selected from the group consisting of: 1 9 7 _C1 -CG alkyl, C ^ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₃ haloalkyl, C ₃ -CG cycloalkyl, C ₇ -C ₂ Q polycycloalkyl, C ₃ -C ₁₆ polyalkoxyalkyl, C2 ~ C ₍ hydroxyalkyl, Ct-C 1-4 alkoxyalkyl, C ₃ -Cg carboalkyl alkyl, C ₄ -Cg cycloalkylalkyl, Cg-Cg alkylcycloalkyl, C ₄ -C ₇ cycloalkylimino, C ₂ -C ₁ alkylimino, Ci-Cß Alkylamino, C ₄ -C -Jp dialkylaminoalkyl, Cg-C ₁₀ cycloalkenyl, phenyl, Alkylphenyl wherein the alkyl is a C ₁ -C ₄ alkyl, Parachloroalkylphenyl wherein the alkyl is a CJC ₄ alkyl, Napthy1, anthracenyl, Benzamidocycloalkyl wherein the alkyl is a C ₁ -C ₃ alkyl, Pyranylmethyl, tetrahydrofurfuryl, thiophenemethyl, benzhydryl, halobenzhydryl, polycyclic alcohol, and substituted phenyl wherein the substituents are selected are made up of the group: C ₁ -C ₄ alkyl, halogen, Nitro,. ^ _X Trifluoromethyl, formyl, chloroacetyl, 219743 C - ^ - C. Alkoxy, hydrogen, benzyl, Chlorobenzyl, phenethyl, and substituted phenethyl wherein the substituents selected are made up of the group: C ₁ -C 4 alkyl, halogen, and R, τ is selected from the group consisting of: C ₁ -C ₄ alkyl, C ₃ -C ₆ alkoxyalkyl, and C ₃ -C ₄ alkenyl, R, Q and Rt ₁ together form heterocyclic compounds form selected from the group consisting of: Azepinyl, morpholinyl, piperdinyl, C ₁ -C ₃ alkyl substituted piperdinyl, with the proviso that when X is O or S, R, q is not hydrogen and substituted phenyl wherein the substituents are selected from the group consisting of : halogen C ₁ -C ₄ alkoxy, phenoxy, trifluoromethyl, C ₁ -Cg thioalkyl, nitro, Ispcyanato, ^C 2 ~ ^C 4 ^Pol y ^al koxy, C ₃ -C ₇ cycloalkyl, C ₃ -C, _o carboalkoxyalkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ alkenyl, C2-C ,. Dialkylamino, phenylamino, C ₁ -C ₄ alkyl, 219743 , 776 - C ₃ -C ₁₂ hydroxyalkylamidoalkyl,
Cc-C ₁ QN, N-hydroxyalkyl ureidoalkyl, isocyanatoalkyl wherein the alkyl is a C ₁ -C ₅ alkyl, C ₃ -C ₂ alkylamidoalkyl, Polyalkoxyamidoalkyl wherein the polyalkoxy moiety has between 3 and 6 repeating C ₃ -C ₃ alkoxy units and the amidoalkyl moiety has between 4 and 12 carbon atoms,
-SO ₂ Cl, -SO ₂ polyalkoxyamidoalkyl wherein the polyalkoxy moiety has between 3 and 6 repeating C ₂ -C ₃ alkoxy units and the amidoalkyl moiety has between 4 to 12 carbon atoms _f R _{5 is} selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl, C ₃ -C ₆ alkoxyalkyl, C ₃ -C. Alkenyl, hydroxyethyl, and phenyl. R. and Rc together form heterocyclic compounds selected from the group consisting of: Azepinyl, morpholinyl, and piperdinyl and C ₁ -C ₃ alkyl-substituted piperdinyl. ° wherein X is 0 or S, η is 0 or list, R ^ is selected from the group consisting of: C ₁ -C ₁₂ alkyl, C ₂ -C ₆ haloalkyl, phenyl, and substituted phenyl where n = 1, the substituents are selected from the group consisting of: nitro, 219743 Chlorine, C ₁ -C ₂ alkyl, C ₃ -Cg cycloalkyl, C ₃ -C ₄ alkenyl. C ₃ -C, alkoxyalkyl, C ₂ -C ₆ hydroxyalkyl, Cy-Co carboxyalkyl, Cc-Cg trialkylammonium alkyl salts, and if η = O the substituents are selected the group consisting of: Chlorine, Thiokalium, C ₁ -C ₁₂ alkyl, benzyl, Cj-C ₂ heteroalkyl, C ₂ -C ₄ chlorocarboxyalkyl, C ₄ -C ₆ polyalkoxyalkyl and acetyl. 0 0 ! * "_ where R _{7 is} selected from the group ' consisting of : where η = O to 8, where M is H or Cl, -CCl = CCl-, -CH ₂ OCH ₂ -, -OCH ₂ CH ₂ O-, and 1 9 d = O or 1 if d = 1 Y is selected from the group consisting of: -S, and -NH, and Z is selected from the group consisting of: C ₁ -C ₁₂ alkyl, hydrogen, C ₄ -C ₁ ^ polyalkoxyalkyl,. C ₄ -Cn dialkylaminoalkyl, C ₃ -C ₅ alkynyl, phenyl, substituted phenyl, organic salts, inorganic salts and if d = 0, Z is selected from Cl or SR ₂ "NC ³⁰ NRi wherein R, R ₁ and R ₀ are as defined above R H / r »ν where R _{fl is} selected from the group -PQKg) ₂ ^{b w} off: C ₁ -C ₅ alkoxy, amino, C ₁ -C ₅ alkoxyamino, hydroxy, and organic base; -SO R "where w = 0-2 and R" is selected from the group consisting of : Amino, · C ₁ -C ₅ alkyl, C ₁ -C ₄ haloalkyl, phenyl, C ₁ -C ₁ Q dialkylamino, C ₁ -C _1n alkylamino, 219743 C ₁ -C ₅ alkoxy, substituted phenyl wherein the substituents are selected are made up of the group: nitro, Chlorο, C ₁ -C ₄ alkyl, and Methoxy. 5. A composition according to item 1, characterized in that in the active compound R3 is selected from carboalkoxyalkyl wherein the alkyl is a C-, -C, alkyl, alkylketoalkyl wherein the alkyl is a C 1-4 alkyl, hydroxyalkenyl wherein the alkenyl a C3-C, is alkyl, hydroxyalkyl wherein the alkyl is a CjCi alkyl, formylhydroxymethyl, Hydroxyhaloethyl where the halo is chloro, substituted phenoxyalkyl wherein the alkyl is a C 1-6 alkyl and the substituents are p-methoxy, Cl, NO ₃ or CN, -ft where R is -OH, -NH ₂ or methoxy, OH OH ^S ₍ ^R 2 -CH-CHN-C = NR ₁ where R, R ₁ and R have the abovementioned meaning, where R, R ₁ and R "are as defined above, 0 OH -PO ₃ -B, -PO ₂ -B or -SO ₃ .B where B is an organic base selected from the group consisting of - H- from: (CH ₃ ) _and OR, Il / * ~ CN
R where R. is selected from the group 5 consisting of: Hydrogen, C ₁ -C ₀ alkyl, hydroxyethyl, naphthyl, χ o Phenyl, substituted phenyl wherein the substituents are independently selected from the group consisting of chlorine, C ₁ -C ₂ alkyl, C ₁ H 4 alkoxy, nitro, cyano and -CF-, Il SR ₀ I ^l NHCN-C = NR ₁ R where R, i and R "have the definition given above. where R, R, and R have the definition given above. CH ₂ NHCN-C = NR ₁ R CH ^ wherein R, R ₁ and R "have the definition given above. ι » ι NHCN-C = NR ₁ ι * - where R, R and R are as defined above. - 2-2 - 219743 _ ZSI where R, R, uhd R have the definition given above, NHC-NC = NR ₁ CH. NHC NH where χ is 1 to 8 and R, R and R "have the definition given above, NHC-NC = NR ₁ 'R where m is 2 or 3 and R, R and R ₂ are as defined above, KHC-NC = NR ₁ ^/ R where R, R, and R "have the above ancillary definition, 0 f ^R 2 NHC-NC = NR ₁ where R, R, and R2 are as defined above _t fig !! 1 & NHCXR ₁₀ where X is selected from the group consisting of: 0 S, ' NH, NR-, -j / and Y is hydrogen or methyl, R, _{o is} selected from the group consisting of: -H, C ₁ -C ₂ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, C ₂ -C ₃ haloalkyl, C ₃ -C ₈ cycloalkyl, Cy-C ₂₀ polycycloalkyl, C ₂ -C ₁₆ polyalkoxyalkyl, C ₂ -Cg hydroxyalkyl, C ₃ - C ₁₀ alkoxyalkyl, C 1 -C ₈ carboalkoxyalkyl, C ₄ -C ₈ cycloalkylalkyl, C ₆ -C ₆ alkylcycloalkyl, C ₄ -C 7 cycloalkylimino, C ₂ -C 4 -alkylimino, C ₁ -C ₃ alkylamino, C ₄ -C ₁₂ dialkylaminoalkyl, C, -C, _o cycloalkenyl, phenyl, Alkylphenyl, wherein the alkyl is a C ₁ -C ₄ alkyl, Parachloroalkylphenyl wherein the alkyl is a C, -C4 alkyl is, Napthyl, anthracenyl, Benzamidocycloalkyl, wherein the alkyl is a C-, -C_ alkyl is 219743 Paranylmethyl, tetrahydrofurfuryl, thiophenemethyl, benzhydryl, ilalobenzhydryl, polycyclic alcohol, and substituted phenyl wherein the substituents are selected from the group consisting of: Ci-C ₄ alkyl,
Halogen,
nitro, Trifluoromethyl, formyl,
Chloroacetyl, C -, - C ₄ alkoxy, hydrogen, benzyl,
Chlorobenzyl, phenethyl and substituted phenethyl wherein the substituents are selected from the group consisting of C ₁ -C ₄ alkyl and
Halogen and R ,, is selected from the group consisting of: Ci-C ₄ alkyl,
C ^ -C _fi alkoxyalkyl, and
C ₃ -C ₄ alkenyl, R, _n and R, - together form heterocyclic compounds are preferably heterocyclic compounds selected from the group consisting of: azepinyl, morpholinyl, piperidinyl, C] _- C3 alkyl substituted Piperdinyl, and with the proviso that when X is O or S, R, "is not hydrogen and substituted phenyl of the substituents are selected from the group 197 consisting of : Halogen, C, -C ₄ alkoxy, phenoxy, trifluoromethyl, CJC, thioalkyl, nitro, Isocyanato, C ₃ -C ₄ polyalkoxy, C ₃ -C ₇ cycloalkyl, C, -C ₄ haloalkyl, C ₃ -C ₄ alkenyl, C ₂ -C, dialkylamino, phenylamino C ₁ -C ₄ alkyl, C ₃ -CjP, hydroxyalkylamidoalkyl, C ₁ -C ₄ , N, N-hydroxyalkyl-ureidoalkyl, isocyanatoalkyl wherein the Alkyl is C, -Cr alkyl, CJC ₁₂ alkylamidoalkyl, Polyalkoxyaraidoalky1 wherein the polyalkoxy moiety has 3 to 6 C "-C" repeating units, alkoxy units and the amidoalkyl moiety has 4-12 carbon atoms, -SO ₂ Cl, -SOp polyalkoxyamidoalkyl wherein the Polyalkoxyeinheit having 3 to 6 repeating C2 ~ _C3 alkoxy units and the Amidoalkyleinheit 4-12 carbon atoms, R ₁ - is selected from the group consisting of hydrogen, C ₁ -C ₄ alkyl,
C 1 -C 6 alkoxyalkyl,
C3-C4 alkenyl,
Hydroxyethyl and
Phenyl. , R ₄ and R ₁ - form heterocyclic compounds selected from the group consisting of:
azepinyl,
morpholinyl, 219743 -ZiS- Piperdinyl, and O-C-) alkyl-substituted piperdinyl, (I -CX _n R _n wherein ⁿ represents 0 or S and X ° η 0 or 1 R is selected from the group consisting of the C ₁ -C ₄ alkyl, - C ₀ -C ,. Haloalkyl, £ 6 Phenyl and substituted phenyl wherein if η = 1, the substituents be selected from the group consisting of: Nitro, chloro, C ₁ -C ₂ -alkyl, Q ^ -Q. Polyalkoxyalkyl, C -, - C _o cycloalkyl, C3-C. Alkenyl, C ^ ^- C ₆ alkoxyalkyl, C ₂ -CG hydroxyalkyl, C ₁ -C ₃ carboxyalkyl, Cc ~ C _R Trialkylammoniumalkylsalzen, and if η = O the substituents are selected the group consisting of: Chloro, Thiokalium, Benzyl, C ₁ -C ₂ heteroalkyl, C ₃ -C ₄ chloro-carboxyalkyl, C ₄ -C, polyalkoxyalkyl, and acetyl. O O " ¹ ^ where R _{n is} selected from the group '° consisting of: - (CH -) where η = O to 8, -CH = CH-, 2197 43 where M represents H or Cl. --CCl = CCl,
-CH ₂ OCH ₂ -, ₂ CH ₂ Q-, and
d = 0 or 1 if d = 1 Y is selected from the group consisting of -S, and -NH, and Z is selected from the group consisting of: C ₁ -C ₄ alkyl, Hydrogen, C ₄ -C _R dialkylaminoalkyl,
C ₃ -C ₅ alkynyl,
phenyl, substituted phenyl,
organic salts,
inorganic salts, and
if d = 0, Z is Cl or SR wherein R, R ₁ and R "are as defined above. Il - P (R ₀ ) _ where R _{0 is} selected from the ο Z. ο Group consisting of: Cj-Cj alkoxy,
amino, 2IS743: - as? - C -, - Cc alkoxyamino, hydroxy and organic base; -SO Rg where w = 0-2 and R "is selected from the group consisting of Amino, C ₁ -C ₅ alkyl, C ₁ -C ₄ haloalkyl, phenyl, C ₁ -C ₁₀ dialkylamino, C ₁ -C ₁₀ alkylamino, C 1 -C ₅ alkoxy, substituted phenyl wherein the substituents are selected are selected from the group consisting of nitro, Chlorο, C ₁ -C ₄ alkyl and Metho: duration is defined · "· ¹ ·. 6. Composition according to item 1, characterized that R is -sekC, Η, _c , R ₁ -C - H, -, R _n -C ₁ Hc and R-, -. / Ib i ο 1-3 ί 2. D -J l'n represent -CCOC ₂ H ₅ . 7. Composition according to item 1, characterized R is -SCkC ₇ H ₁₅ , R _{1 is} CgH ₁₇ , R _{3 is} -CH _{3 and} R ₃ -CNHC is ₁₈ H ₃₇ . 8. Composition according to item 1, characterized that R -sekC-H ,, R ₁ -C ₀ H,.,, R ₀ -C _n H ₁ . and R., / Id 1 Hl / ^ ZD J -CNHC ₁₈ H ₃₇ represent. 9. The composition according to item 1, characterized in that R -sekC ₇ H ₁₅ , R ₁ -C ₃ H ₁₇ , R ₃ ~ ^C ₂ ^H 5 ^{and R} 3 Represent -CCOC ₂ H ₅ . 2197 -Ai * - 10. The composition according to item 1, characterized in that R, R, R ₂ / and R ₃ are selected so that the compound have no phytotoxic properties, and that by applying a 0.05 weight percent solution of the composition to the place of residence or the food the lepidoptera will get an LD ₅₀ effect.