This invention discloses new chemical compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of hydrogen, alkyl and alkenyl; R.sup.2 is selected from the group consisting of alkyl, alkenyl, cycloalkyl and ##STR2## WHEREIN Z is selected from the group consisting of alkyl, alkenyl, alkoxy, halogen, nitro and alkylthio; p is an integer from 0 to 5; and m is the integer 0 or 1; X.sup.1 and X.sup.2 are each selected from the group consisting of hydrogen, alkyl and halogen; Y is selected from the group consisting of oxygen and sulfur; n is the integer 1 or 2; and R.sup.3 and R.sup.4 are each alkyl.

This invention relates to new compositions of matter and more specifically 
relates to new chemical compounds of the formula 
##STR3## 
wherein R.sup.1 is selected from the group consisting of hydrogen, alkyl 
and alkenyl; R.sup.2 is selected from the group consisting of alkyl, 
alkenyl, cycloalkyl and 
##STR4## 
WHEREIN Z is selected from the group consisting of alkyl, alkenyl, alkoxy, 
halogen, nitro and alkylthio; p is an integer from 0 to 5; and m is the 
integer 0 or 1; X.sup.1 and X.sup.2 are each selected from the group 
consisting of hydrogen, alkyl and halogen; Y is selected from the group 
consisting of oxygen and sulfur; n is the integer 1 or 2; and R.sup.3 and 
R.sup.4 are each alkyl. 
In a preferred embodiment of the present invention R.sup.1 is selected from 
the group consisting of hydrogen, lower alkyl and lower alkenyl; R.sup.2 
is selected from the group consisting of lower alkyl, lower alkenyl, 
cycloalkyl of from 3 to 7 carbon atoms and 
##STR5## 
WHEREIN Z is selected from the group consisting of lower alkyl, lower 
alkenyl, lower alkoxy, chlorine, bromine, fluorine, nitro and lower 
alkylthio; p is an integer of from 0 to 3; and m is the integer 0 or 1; 
X.sup.1 and X.sup.2 are each selected from the group consisting of 
hydrogen, lower alkyl, chlorine and bromine, Y is selected from the group 
consisting of oxygen and sulfur; n is the integer 1 to 2; and R.sup.3 and 
R.sup.4 are each lower alkyl. 
The term "lower" as used herein designates a straight or branched carbon 
chain of up to six carbon atoms. 
The compounds of the present invention are useful as insecticides. 
The compounds of the present invention can be prepared by reacting a 
compound of the formula 
##STR6## 
wherein X.sup.1, X.sup.2, Y, n, R.sup.3 and R.sup.4 are as heretofore 
described with a carbamoyl chloride of the formula 
##STR7## 
wherein R.sup.1 and R.sup.2 are as heretofore described. This reaction can 
be effected by incrementally adding the carbamoyl chloride of formula III 
to a solution of the compound of formula II in an inert organic reaction 
medium at room temperature and in the presence of an acid acceptor such as 
an alkali metal carbonate or bicarbonate or a tertiary amine. About 
equimolar amounts of the reactants can be effectively used. After the 
addition is completed, the reaction mixture can be heated at its reflux 
temperature for a period of up to about several hours to ensure completion 
of the reaction. 
The compounds of the present invention wherein R.sup.1 is hydrogen can also 
be prepared by reacting the compound of formula II with an isocyanate of 
the formula 
EQU R.sup.2 --N.dbd.C.dbd.O (IV) 
wherein R.sup.2 is as heretofore described. This reaction can be effected 
by incrementally adding an equimolar or slight excess molar amount of the 
isocyanate to a solution of the compound of formula II in an inert organic 
solvent such as benzene at room temperature. A catalytic amount of 
triethylamine can be used to aid in the reaction. After the isocyanate 
addition is completed, the reaction mixture can be stirred for an 
additional period of up to about 8 hours to ensure completion of the 
reaction. After this time the reaction mixture can be filtered and the 
filtrate stripped of solvent to yield the desired product, which can be 
used as such or can be further purified by standard techniques well known 
in the art. 
The compounds of formula II can be prepared by reacting a compound of the 
formula 
##STR8## 
wherein X.sup.1, X.sup.2 and Y are as heretofore described, with a 
compound of the formula 
##STR9## 
wherein Hal designated halogen and n, R.sup.3 and R.sup.4 are as 
heretofore described. This reaction can be effected by incrementally 
adding the compound of formula VI to a solution of the compound of formula 
V in an inert organic solvent such as dimethylformamide at room 
temperature. About equimolar amounts of the reactants can be utilized. 
After the addition is completed, the reaction mixture can be heated under 
a nitrogen atmosphere at a temperature ranging up to the reflux 
temperature of the mixture for a period of up to about 50 hours. After 
this time water can be added to the reaction mixture and the mixture 
neutralized. The organic phase can then be separated from the aqueous 
phase and can be stripped of solvent to yield the desired product. This 
product can be used as such or can be further purified as desired. 
The compounds of formula V can be prepared by reacting a compound of the 
formula 
##STR10## 
wherein X.sup.1, X.sup.2 and Y are as heretofore described, with an 
equimolar amount of sodium methoxide. This reaction can be effected by 
combining an alcoholic solution of sodium methoxide with a solution of the 
compound of formula VII in methanol at room temperature with stirring. 
After the addition is completed, the mixture can be warmed and stirring 
continued for a period of up to about 60 minutes. After this time the 
mixture can be stripped of solvent to yield the desired product as the 
residue. 
Exemplary compounds of formula VII useful for preparing the compounds of 
the present invention are hydroquinone, resorcinol, 4-methylresorcinol, 
5-methylresorcinol, 2,5-dihydroxytoluene, 1,3-dihydroxy-4-chlorobenzene, 
2-methyl-3-hydroxyphenol, 2-chloro-3-hydroxyphenol, 
2-methyl-4-hydroxyphenol, 3-mercaptophenol, 4-mercaptophenol, 
3-mercapto-5-methylphenol, 3-mercapto-5-bromophenol, 
3-mercapto-5-iodophenol, 4-mercapto-5-chlorophenol and the like. 
Exemplary compounds of formula VI useful for preparing the compounds of 
this invention are 1-chloro-2,2-dimethoxyethane, 
1-chloro-2,2-diethoxyethane, 1-chloro-2,2-dipropoxyethane, 
1-chloro-2,2-dibutoxyethane, 1-chloro-3,3-dimethoxypropane, 
1-chloro-3,3-diethoxypropane, 1-chloro-3,3-dipropoxypropane and the like. 
Exemplary suitable isocyanates of formula IV are methyl isocyanate, ethyl 
isocyanate, propyl isocyanate, butyl isocyanate, pentyl isocyanate, hexyl 
isocyanate, allyl isocyanate, but-3-enyl isocyanate, pent-4-enyl 
isocyanate, hex-4-enyl isocyanate, cyclopropyl isocyanate, cyclobutyl 
isocyanate, cyclopentyl isocyanate, cyclohexyl isocyanate, cycloheptyl 
isocyanate, phenyl isocyanate, 4-methylphenyl isocyanate, 3-chlorophenyl 
isocyanate, 3,4-dichlorophenyl isocyanate, 4-bromophenyl isocyanate, 
4-fluorophenyl isocyanate, 4-iodophenyl isocyanate, 3-allylphenyl 
isocyanate, 4-hex-3-enylphenyl isocyanate, 2-methoxyphenyl isocyanate, 
3-ethoxyphenyl isocyanate, 4-propoxyphenyl isocyanate, 3,5-dinitrophenyl 
isocyanate, 2-ethyl-4-chlorophenyl isocyanate, 3,4,5-trimethylphenyl 
isocyanate, 2-methylthiophenyl isocyanate, 4-t-butylphenyl isocyanate, 
benzyl isocyanate and the like. 
Exemplary carbamoyl chlorides of formula III are methylcarbamoyl chloride, 
ethylcarbamoyl chloride, N,N-dimethylcarbamoyl chloride, 
N,N-diethylcarbamoyl chloride, N,N-dipropylcarbamoyl chloride, 
N-methyl-N-cyclopropylcarbamoyl chloride, N-methyl-N-phenylcarbamoyl 
chloride, N-ethyl-N-(3-chlorophenyl)carbamoyl chloride, 
N-methyl-N-(2,4,6-trichlorophenyl)carbamoyl chloride, 
N-methyl-N-benzylcarbamoyl chloride, N-allyl-N-(3-methylbenzyl)carbamoyl 
chloride and the like.

The manner in which the compounds of the present invention can be prepared 
is more specifically illustrated in the following examples. 
EXAMPLE 1 
Preparation of the Monosodium Salt of Hydroquinone 
Hydroquinone (11.0 grams; 0.10 mole) and methanol (20 ml) were charged into 
a glass reaction vessel equipped with a mechanical stirrer and 
thermometer. The vessel was purged with nitrogen gas and sodium (2.3 
grams) dissolved in methanol (30 ml) was added with continued stirring. 
After a period of about 15 minutes the reaction mixture was stripped of 
methanol under aspirator pressure to yield the desired product, the 
monosodium salt of hydroquinone as a white solid residue. 
EXAMPLE 2 
Preparation of 4-(2,2-Dimethoxyethoxy)phenol 
The monosodium salt of hydroquinone prepared in Example 1 and dimethyl 
formamide (100 ml) were charged under nitrogen gas into a glass reaction 
vessel equipped with a mechanical stirrer, thermometer and addition funnel 
and were warmed to effect dissolution. The resulting solution was then 
allowed to warm to room temperature, and 1-chloro-2,2-dimethoxyethane was 
added dropwise over a period of about 20 minutes. After the addition was 
completed, the reaction mixture was heated at about 85.degree. to 
90.degree. C. with stirring for a period of about 48 hours. After this 
time water (200 ml) was added, and the reaction mixture was neutralized 
with ammonium chloride. The reaction mixture was then extracted with 
chloroform, and the organic phase was separated from the aqueous phase. 
The organic phase was then stripped of solvent, leaving a red oil. This 
oil was distilled to yield the desired product 
4-(2,2-dimethoxyethoxy)phenol as a pink oil boiling at 116.degree. to 
120.degree. C. at 0.008 mm of Hg pressure. 
EXAMPLE 3 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] N-Methylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (5.0 grams) and benzene were charged into a 
glass reaction vessel equipped with a mechanical stirrer. Methyl 
isocyanate (3.5 ml) and 4 drops of triethylamine were then added, and the 
reaction mixture was stirred at room temperature for a period of about 6 
hours. After this time the reaction mixture was filtered, and the filtrate 
was concentrated to 10 ml by partially stripping the solvent under reduced 
pressure. Cyclohexane (10 ml) was then added to the concentrate, resulting 
in the formation of a precipitate. The precipitate was recovered by 
filtration to yield the desired product O-[4-(2,2-dimethoxyethoxy)phenyl] 
N-methylcarbamate as a slightly pink solid melting at 79.degree. to 
81.degree. C. 
EXAMPLE 4 
Preparation of the Monosodium Salt of 5-Methylresorcinol 
5-Methylresorcinol monohydrate (14.2 grams; 0.10 moles) dissolved in 
methanol (20 ml) was charged into a glass reaction vessel equipped with a 
mechanical stirrer and thermometer. The reaction mixture was blanketed 
with nitrogen gas, and sodium methoxide prepared by combining sodium (2.3 
grams) with methanol (40 ml) was added with stirring. The reaction mixture 
was then heated at 50.degree. C. with continued stirring for a period of 
about 15 minutes. After this time the reaction mixture was stripped of 
solvent under reduced pressure to yield the desired product as a grey 
solid. 
EXAMPLE 5 
Preparation of 3-(2,2-Dimethoxyethoxy)-5-hydroxytoluene 
The monosodium salt of 5-methylresorcinol prepared in Example 4 and 
dimethyl formamide (200 ml) were charged under nitrogen gas into a glass 
reaction vessel equipped with a mechanical stirrer, thermometer and 
addition funnel. 1-Chloro-2,2-dimethoxyethane (6.25 grams) was added, and 
the mixture was heated at 85.degree. to 90.degree. C. and stirred for a 
period of about 221/2 hours. After this time the reaction mixture was 
cooled to room temperature and was added to 1200 ml of water. The 
resulting mixture was carefully neutralized and extracted with chloroform. 
The organic phase was then separated from the aqueous phase and stripped 
of solvent, leaving a liquid residue. The residue was distilled under 
reduced pressure to yield a yellow viscous liquid which solidified upon 
cooling to -10.degree. C. This product was then recrystallized from a 
methanol-water mixture, was washed with boiling water and dried to yield 
the desired product 3-(2,2-dimethoxyethoxy)-5-hydroxytoluene as a white 
solid melting at 73.degree. to 75.degree. C. 
EXAMPLE 6 
Preparation of O-[3-(2,2-Dimethoxyethoxy)-5-methylphenyl] N-Methylcarbamate 
3-(2,2-Dimethoxyethoxy)-5-hydroxytoluene (2.50 grams), benzene (50 ml) and 
triethylamine (4 drops) were charged into a glass reaction vessel equipped 
with a mechanical stirrer. Methyl isocyanate (1.0 ml) was added to the 
vessel, and the resulting mixture was stirred at room temperature for a 
period of about 2 hours. The mixture was then allowed to stand at ambient 
temperature over the weekend. After this time the reaction mixture was 
stripped of benzene, leaving a viscous liquid residue. This residue was 
distilled under vacuum to yield the desired product 
O-[3-(2,2-dimethoxyethoxy)-5-methylphenyl] N-methylcarbamate as an oil. 
EXAMPLE 7 
Preparation of S-Sodium Salt of 3-Mercaptophenol 
3-Mercaptophenol (3.15 grams) dissolved in methanol (5 ml) was charged into 
a glass reaction vessel equipped with a mechanical stirrer and 
thermometer. The reaction mixture was blanketed with nitrogen gas, and 
sodium methoxide, prepared by combining sodium (0.57 grams) and methanol 
(10 ml), was added with stirring. After the addition was completed, the 
mixture was heated with continued stirring for a period of about 15 
minutes. After this time the reaction mixture was stripped of methanol 
under reduced pressure to yield the desired product S-sodium salt of 
3-mercaptophenol as a semisolid residue. 
EXAMPLE 8 
Preparation of 3-(2,2-Dimethoxyethylthio)phenol 
The S-sodium salt of 3-mercaptophenol prepared in Example 7 was dissolved 
in dimethylformamide (25 ml) and charged under nitrogen gas into a glass 
reaction vessel equipped with a mechanical stirrer, thermometer and 
addition funnel. The solution was heated to a temperature of 45 to 
50.degree. C., and 1-chloro-2,2-dimethoxyethane (3.15 grams) was added 
with stirring. After the addition was completed, stirring was continued 
for a period of about 3 hours. After this time the reaction mixture was 
poured into water (150 ml), and the resulting mixture was carefully 
neutralized with ammonium chloride. The mixture was then extracted with 
chloroform and the organic phase was separated. The organic portion was 
washed with water and then dried with phase separation paper. The dried 
solution was then stripped of solvent, leaving an oil. This oil was 
distilled, and the fraction boiling at 138.degree. to 144.degree. C. at 
0.04 mm of Hg pressure was collected to yield the desired product 
3-(2,2-dimethoxyethylthio)phenol. 
EXAMPLE 9 
Preparation of O-[3-(2,2-Dimethoxyethylthio)phenyl] N-Methylcarbamate 
3-(2,2-Dimethoxyethylthio)phenol (1.80 grams) dissolved in benzene (5 ml) 
was charged into a glass reaction vessel equipped with a mechanical 
stirrer. Methyl isocyanate (12 ml) and trimethylamine (2 drops) were then 
added, and the resulting mixture was stirred at room temperature for a 
period of about 51/2 hours. The mixture was then allowed to stand 
overnight and was then stripped of excess methyl isocyanate and a portion 
of the benzene. The concentrated solution was then added to ether and 
cooled to -60.degree. C., resulting in a precipitate. The precipitate was 
recrystallized from ether to yield the desired product 
O-[3-(2,2-dimethoxyethylthio)phenyl]-0 N-methylcarbamate having a melt 
point of 46.degree. to 48.degree. C. 
EXAMPLE 10 
Preparation of the Monosodium Salt of Resorcinol 
Resorcinol (0.10 mole) and methanol (20 ml) are charged into a glass 
reaction vessel equipped with a mechanical stirrer and thermometer. Sodium 
(0.10 mole) dissolved in methanol (30 ml) is then added under nitrogen gas 
to the reaction vessel with continued stirring. After a period of about 15 
minutes the reaction mixture is stripped of methanol under aspirator 
pressure to yield the desired product the monosodium salt of resorcinol as 
the residue. 
EXAMPLE 11 
Preparation of 4-(3,3-Dimethoxypropoxy)phenol 
The monosodium salt of hydroquinone (0.05 mole) and dimethylformamide (75 
ml) are charged under nitrogen gas into a glass reaction vessel equipped 
with a mechanical stirrer, thermometer and addition funnel. The mixture is 
stirred until dissolved, and 1-chloro-3,3-dimethoxypropane (0.05 mole) is 
added dropwise over a period of about 20 minutes. After the addition is 
completed, the reaction mixture is heated at about 90.degree. C. with 
stirring for a period of about 48 hours. After this time water (200 ml) is 
added, and the reaction mixture is carefully neutralized with ammonium 
chloride. The reaction mixture is then extracted with chloroform, and the 
organic phase is separated from the aqueous phase. The organic phase is 
then stripped of solvent, leaving an oil. This oil is distilled under 
reduced pressure to yield the desired product 
4-(3,3-dimethoxypropoxy)phenol. 
EXAMPLE 12 
Preparation of O-[4-(3,3-Dimethoxypropoxy)phenyl] N-Allylcarbamate 
4-(3,3-Dimethoxypropoxy)phenol (0.05 mole) dissolved in benzene (10 ml) is 
charged into a glass reaction flask equipped with a mechanical stirrer. 
Allyl isocyanate (0.06 mole) and triethylamine (3 drops) are then added, 
and the resulting mixture is stirred at room temperature for a period of 
about 6 hours. The dried solution is stirpped of solvent and unreacted 
isocyanate to yield the desired product O-[4-(3,3-dimethoxypropoxy)phenyl] 
N-allylcarbamate as the residue. 
EXAMPLE 13 
Preparation of 3-(2,2-Diethoxyethoxy)-5-chlorophenol 
The monosodium salt of 3-hydroxy-5-chlorophenol (0.05 mole) and 
dimethylformamide (75 ml) are charged under nitrogen gas into a glass 
reacton vessel equipped with a mechanical stirrer, thermometer and 
addition funnel. The mixture is stirred until dissolved, and 
1-chloro-2,2-diethoxyethane (0.05 mole) is added dropwise over a period of 
about 20 minutes. After the addition is completed, the reaction mixture is 
heated at about 90.degree. C. with stirring for a period of about 48 
hours. After this time water (200 ml) is added, and the reaction mixture 
is neutralized with ammonium chloride. The reaction mixture is then 
extracted with chloroform, and the organic phase is separated from the 
aqueous phase. The organic phase is then stripped of solvent, leaving an 
oil. This oil is distilled under reduced pressure to yield the desired 
product 3-(2,2-diethoxyethoxy)-5-chlorophenol. 
EXAMPLE 14 
Preparation of O-[3-(2,2 -Diethoxyethoxy)-5-chlorophenyl] N-Phenylcarbamate 
3-(2,2-Diethoxyethoxy)-5-chlorophenol (0.05 mole) dissolved in benzene (10 
ml) is charged into a glass reaction flask equipped with a mechanical 
stirrer. Phenyl isocyanate (0.06 mole) and triethylamine (3 drops) are 
then added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[3-(2,2-diethoxyethoxy)-5-chlorophenyl] N-phenylcarbamate as the 
residue. 
EXAMPLE 15 
Preparation of 3-(2,2-Dimethoxyethoxy)-5-bromophenol 
The monosodium salt of 3-hydroxy-5-bromophenol (0.05 mole) and 
dimethylformamide (75 ml) are charged under nitrogen gas into a glass 
reaction vessel equipped with a mechanical stirrer, thermometer and 
additional funnel. The mixture is stirred until dissolved, and 
1-chloro-2,2-dimethoxyethane (0.05 mole) is added dropwise over a period 
of about 20 minutes. After the addition is completed, the reaction mixture 
is heated at about 90.degree. C. with stirring for a period of about 48 
hours. After this time water (200 ml) is added, and the reaction mixture 
is neutralized with ammonium chloride. The reaction mixture is then 
extracted with chloroform, and the organic phase is separated from the 
aqueous phase. The organic phase is then stripped of solvent, leaving an 
oil. This oil is distilled under reduced pressure to yield the desired 
product 3-(2,2-dimethoxyethoxy)-5-bromophenol. 
EXAMPLE 16 
Preparation of O-[3-(2,2-Dimethoxyethoxy)-5-bromophenyl] 
N-2-Methylphenylcarbamate 
3-(2,2-Dimethoxyethoxy)-5-bromophenol (0.05 mole) dissolved in benzene (10 
ml) is charged into a glass reaction flask equipped with a mechanical 
stirrer. 2-Methylphenyl isocyanate (0.06 mole) and triethylamine (3 drops) 
are then added, and the resulting mixture is stirred at room temperature 
for a period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[3-(2,2-dimethoxyethoxy)-5-bromophenyl] N-2-methylphenylcarbamate as the 
residue. 
EXAMPLE 17 
Preparation of 4-(2,2-Dipropoxyethylthio)phenol 
The S-monosodium salt of 4-mercaptophenol (0.05 mole) and dimethylformamide 
(75 ml) are charged into a glass reaction vessel equipped with a 
mechanical stirrer, thermometer and addition funnel. The mixture is 
stirred until dissolved, and 1-chloro-2,2-dipropoxyethane (0.05 mole) is 
added dropwise over a period of about 20 minutes. After the addition is 
completed, the reaction mixture is blanketed with nitrogen gas and is 
heated at about 90.degree. C. with stirring for a period of about 48 
hours. After this time water (200 ml) is added, and the reaction mixture 
is neutralized with ammonium chloride. The reaction mixture is then 
extracted with chloroform, and the organic phase is separated from the 
aqueous phase. The organic phase is then stripped of solvent, leaving an 
oil. This oil is distilled under reduced pressure to yield the desired 
product 4-(2,2-dipropoxyethylthio)phenol. 
EXAMPLE 18 
Preparation of O-[4-(2,2-Dipropoxyethylthio)phenyl] N-Cyclopropylcarbamate 
4-(2,2-Dipropoxyethylthio)phenol (0.05 mole) dissolved in benzene (10 ml) 
is charged into a glass reaction flask equipped with a mechanical stirrer. 
Cyclopropylisocyanate (0.06 mole) and triethylamine (3 drops) are then 
added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[4-(2,2-dipropoxyethylthio)phenyl] N-cyclopropylcarbamate as the 
residue. 
EXAMPLE 19 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] N-3-Allylphenylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole) dissolved in benzene (10 ml) is 
charged into a glass reaction flask equipped with a mechanical stirrer. 
3-Allylphenyl isocyanate (0.06 mole) and triethylamine (3 drops) are then 
added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is stripped of solvent and unreacted 
isocyanate to yield the desired product O-[4-(2,2-dimethoxyethoxy)phenyl] 
N-3-allylphenylcarbamate as the residue. 
EXAMPLE 20 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] N-4-Methoxyphenylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole) dissolved in benzene (10 ml) is 
charged into a glass reaction flask equipped with a mechanical stirrer. 
4-Methoxyphenyl isocyanate (0.06 mole) and triethylamine (3 drops) are 
then added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[4-(2,2-dimethoxyethoxy)phenyl] N-4-methoxyphenylcarbamate as the 
residue. 
EXAMPLE 21 
preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] 
N-3,4-Dichlorophenylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole) dissolved in benzene (10 ml) is 
charged into a glass reaction flask equipped with a mechanical stirrer. 
3,4-Dichlorophenyl isocyanate (0.06 mole) and triethylamine (3 drops) are 
then added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[4-(2,2-dimethoxyethoxy)phenyl] N-3,4-dichlorophenylcarbamate as the 
residue. 
EXAMPLE 22 
Preparation of O-[3-(2,2-Dimethoxyethylthio)phenyl] N-Cyclohexylcarbamate 
3-(2,2-Dimethoxyethylthio)phenol (0.05 mole) dissolved in benzene (10 ml) 
is charged into a glass reaction flask equipped with a mechanical stirrer. 
Cyclohexyl isocyanate (0.06 mole) and triethylamine (3 drops) are then 
added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[3-(2,2-dimethoxyethylthio) phenyl] N-cyclohexylcarbamate as the 
residue. 
EXAMPLE 23 
Preparation of O-[3-(2,2-Dimethoxyethylthio)phenyl] 
N-3-Nitrophenylcarbamate 
3-(2,2-Dimethoxyethylthio)phenol (0.05 mole) dissolved in benzene (10 ml) 
is charged into a glass reaction flask equipped with a mechanical stirrer. 
3-Nitrophenyl isocyanate (0.06 mole) and triethylamine (3 drops) are then 
added and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[3-(2,2-dimethoxyethylthio) phenyl] N-3-nitrophenylcarbamate as the 
residue. 
EXAMPLE 24 
Preparation of O-[3-(2,2-Dimethoxyethylthio)phenyl] 
N-4-Methylthiophenylcarbamate 
3-(2,2-Dimethoxyethylthio)phenol (0.05 mole) dissolved in benzene (10 ml) 
is charged into a glass reaction flask equipped with a mechanical stirrer. 
4-Methylthiophenyl isocyanate (0.06 mole) and triethylamine (3 drops) are 
then added, and the resulting mixture is stirred at room temperature for a 
period of about 6 hours. The mixture is then stripped of solvent and 
unreacted isocyanate to yield the desired product 
O-[3-(2,2-dimethoxyethylthio)-phenyl] N-4-methylthiophenylcarbamate as the 
residue. 
EXAMPLE 25 
Preparation of O-[ 3-(2,2-Dimethoxyethoxy)-5-methylphenyl] 
N,N-Dimethylcarbamate 
3-(2,2-Dimethoxyethoxy)-5-methylphenol (0.05 mole), N,N-dimethylcarbamoyl 
chloride (0.08 mole), triethylamine (0.05 mole) and xylene (50 ml) are 
charged into a glass reaction flask equipped with a mechanical stirrer, 
thermometer and reflux condenser. The mixture is stirred and heated at 
80.degree. C. for a period of about 12 hours. After this time the reaction 
mixture is cooled to room temperature and is filtered. The filtrate is 
then washed with water and dried over anhydrous magnesium sulfate. The 
dried solution is then filtered and stripped of solvent and unreacted 
starting materials to yield the desired product 
O-[3-(2,2-dimethoxyethoxy)-5-methylphenyl] N,N-dimethylcarbamate as the 
residue. 
EXAMPLE 26 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] 
N-Methyl-N-cyclopropylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole), N-methyl-N-cyclopropylcarbamoyl 
chloride (0.08 mole), triethylamine (0.05 mole) and xylene (50 ml) are 
charged into a glass reaction flask equipped with a mechanical stirrer, 
thermometer and reflux condenser. The mixture is stirred and heated at 
80.degree. C. for a period of about 12 hours. After this time the reaction 
mixture is cooled to room temperature and is filtered. The filtrate is 
then washed with water and dried over anhydrous magnesium sulfate. The 
dried solution is then filtered and stripped of solvent and unreacted 
starting materials to yield the desired product 
O-[4-(2,2-dimethoxyethoxy)phenyl] N-methyl-N-cyclopropylcarbamate as the 
residue. 
EXAMPLE 27 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] 
N-Ethyl-N-3,4-dibromophenylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole), 
N-ethyl-N-3,4-dibromophenylcarbamoyl chloride (0.08 mole), triethylamine 
(0.05 mole) and xylene (50 ml) are charged into a glass reaction flask 
equipped with a mechanical stirrer, thermometer and reflux condenser. The 
mixture is stirred and heated at reflux for a period of about 12 hours. 
After this time the reaction mixture is cooled to room temperature and is 
filtered. The filtrate is then washed with water and dried over anhydrous 
magnesium sulfate. The dried solution is then filtered and stripped of 
solvent and unreacted starting materials to yield the desired product 
O-[4-(2,2-dimethoxyethoxy)phenyl] N-ethyl-N-3,4-dibromophenylcarbamate as 
the residue. 
EXAMPLE 28 
Preparation of O-[4-(2,2-Dimethoxyethoxy)phenyl] N-Allyl-N-benzylcarbamate 
4-(2,2-Dimethoxyethoxy)phenol (0.05 mole), N-allyl-N-benzylcarbamoyl 
chloride (0.08 mole), triethylamine (0.05 mole) and xylene (50 ml) are 
charged into a glass reaction flask equipped with a mechanical stirrer, 
thermometer and reflux condenser. The mixture is stirred and heated at 
reflux for a period of about 12 hours. After this time the reaction 
mixture is cooled to room temperature and is filtered. The filtrate is 
then washed with water and dried over anhydrous magnesium sulfate. The 
dried solution is then filtered and stripped of solvent and unreacted 
starting materials to yield the desired product 
O-[4-(2,2-dimethoxyethoxy)phenyl] N-allyl-N-benzylcarbamate as the 
residue. 
Other compounds of the present invention can be prepared readily by the 
procedures described above. Presented in the following examples are the 
essential reactants required to prepare the indicated named compounds 
according to the methods heretofore described. 
EXAMPLE 29 
4-Mercaptophenol+sodium methoxide+1-chloro-2,2-dimethoxyethane+methyl 
isocyanate= O-[4-2,2-dimethoxyethylthio)phenyl] N-methylcarbamate; m.p. 
51.degree. to 52.degree. C. 
EXAMPLE 30 
3-Hydroxy-5-methylphenol+sodium 
methoxide+1-chloro-2,2-diethoxyethane+methyl isocyanate= 
O-[3-(2,2-diethoxyethoxy)-5-methyl] N-methylcarbamate; m.p. 67.degree. to 
69.degree. C. 
EXAMPLE 31 
2-Methyl-3-hydroxyphenol+sodium 
methoxide+1-chloro-2,2-dimethoxyethane+methyl isocyanate= 
O-[3-(2,2-dimethoxyethoxy)-2-methyl] N-methylcarbamate; m.p. 53.degree. to 
56.degree. C. 
EXAMPLE 32 
3-Hydroxy-5-chlorophenol+sodium 
methoxide+1-chloro-2,2-dimethoxyethane+methyl isocyanate= 
O-[3-(2,2-dimethoxyethoxy)-5-chlorophenyl] N-methylcarbamate. 
EXAMPLE 33 
3-Mercapto-5-methylphenol+sodium methoxide 
+1-chloro-2,2-dimethoxyethane+methyl isocyanate= 
O-[3-(2,2-dimethoxyethylthio)-5-methylphenyl] N-methylcarbamate. 
Additional compounds within the scope of this invention which can be 
prepared according to the details of the foregoing examples include 
O-[3-(2,2-dimethoxyethoxy)-4-methylphenyl] N-ethylcarbamate, 
O-[3-(2,2-diethoxyethoxy)-5-ethylphenyl] N-propylcarbamate, 
O-[3-(2,2-dipropoxyethoxy)-5-propylphenyl] N-butylcarbamate, 
O-[3-(2,2-dibutoxypropoxy)-5-butylphenyl] N-pentylcarbamate, 
O-[3-(2,2-dipentyloxyethoxy)-5-pentylphenyl] N-hexylcarbamate, 
O-[3-(2,2-dihexyloxyethoxy)-5-hexylphenyl] N,N-dimethylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)-5-iodophenyl] N,N-diethylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)-5-fluorophenyl] N,N-dipropylcarbamate, 
O-[3-(2-methoxy-2-ethoxyethoxy)-5-methylphenyl] N,N-dibutylcarbamate, 
O-[3-(2-methoxy-2-propoxyethoxy)-5-methylphenyl] N,N-dipentylcarbamate, 
O-[3-(2-methoxy-2-ethoxypropoxy)-5-methylphenyl] N,N-dihexylcarbamate, 
O-[4-(2,2-dimethoxypropylthio)phenyl] N-cyclobutylcarbamate, 
O-[4-(2,2-dipropoxypropylthio)phenyl] N-cyclopentylcarbamate, 
O[4-(2,2-dibutyloxypropylthio)phenyl] N-cyclohexylcarbamate, 
O-[4-(2,2-dipentyloxypropylthio)phenyl] N-cycloheptylcarbamate, 
O-[4-(2,2-dihexyloxypropylthio)phenyl] N,N-diethylcarbamate, 
O-[4-(2,2-dimethoxyethylthio)phenyl] N,N-dipropylcarbamate, 
O-[4-(2,2-diethoxyethylthio)phenyl] N,N-dibutylcarbamate, 
O-[4-(2,2-dipropoxyethylthio)phenyl] N,N-dipentylcarbamate, 
O-[4-(2,2-dibutoxyethylthio)phenyl] N,N-dihexylcarbamate, 
O-[4-(2,2-dipentyloxyethylthio)phenyl] N-but-3-enylcarbamate, 
O-[4-(2,2-dihexyloxyethylthio)phenyl] N-pent-4-enylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-hex-4-enylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-3-ethylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-propylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-3-butylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-pentylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-hexylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-3-but-3-enylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-hex-4-enylphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-2-ethoxyphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-3-propoxyphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-pentyloxyphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-hexyloxyphenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-3,4-dichlorophenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)-phenyl] N-4-fluorophenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)-phenyl] N-4-iodophenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)-phenyl] N-4-bromophenylcarbamate, 
0-[3-(2,2-dimethoxyethoxy)-phenyl] N-4-ethylthiophenylcarbamate, 
O-[3-(2,2-dimethoxyethoxy)phenyl] N-4-propylthiophenylcarbamate, O-[ 
3-(2,2-dimethoxyethoxy)phenyl] N-4-hexylthiophenylcarbamate and the like. 
For practical use as insecticides, the compounds of this invention are 
generally incorporated into insecticidal compositions which comprise an 
inert carrier and an insecticidally toxic amount of such a compound. Such 
insecticidal compositions, which can also be called formulations, enable 
the active compound to be applied conveniently to the site of the insect 
infestation in any desired quantity. These compositions can be solids, 
such as dusts, granules or wettable powders; or they can be liquids such 
as solutions, aerosols or emulsifiable concentrates. 
For example, dusts can be prepared by grinding and blending the active 
compound with a solid inert carrier such as the talcs, clays, silicas, 
pyrophyllite and the like. Granular formulations can be prepared by 
impregnating the compound, usually dissolved in a suitable solvent, onto 
and into granulated carriers such as the attapulgites or the vermiculites, 
usually of a particle size range of from about 0.3 to 1.5 mm. Wettable 
powders, which can be dispersed in water and/or oil to any desired 
concentration of the active compound, can be prepared by incorporating 
wetting agents into concentrated dust compositions. 
In some cases the active compounds are sufficiently soluble in common 
organic solvents such as kerosene or xylene so that they can be used 
directly as solutions in these solvents. Frequently, solutions of 
insecticides can be dispersed under superatmospheric pressure as aerosols. 
However, preferred liquid insecticidal compositions are emulsifiable 
concentrates, which comprise an active compound according to this 
invention and as the inert carrier, a solvent and an emulsifier. Such 
emulsifiable concentrates can be extended with water and/or oil to any 
desired concentration of active compound for application as sprays to the 
site of the insect infestation. The emulsifiers most commonly used in 
these concentrates are nonionic or mixtures of nonionic with anionic 
surface-active agents. 
A typical insecticidal composition according to this invention is 
illustrated by the following example, in which the quantities are in parts 
by weight. 
EXAMPLE 34 
Preparation of a Dust 
Product of Example 3 10 
Powdered talc 90 
The above ingredients are mixed in a mechanical grinder-blender and are 
ground until a homogeneous, free-flowing dust of the desired particle size 
is obtained. This dust is suitable for direct application to the site of 
the insect infestation. 
The compounds of this invention can be applied as insecticides in any 
manner recognized by the art. One method for destroying insects comprises 
applying to the locus of the insect infestation, an insecticidal 
composition comprising an inert carrier and, as the essential active 
ingredient, in a quantity which is toxic to said insects, a compound of 
the present invention. The concentration of the new compounds of this 
invention in the insecticidal compositions will vary greatly with the type 
of formulation and the purpose for which it is designed, but generally the 
insecticidal compositions will comprise from about 0.05 to about 95 
percent by weight of the active compounds of this invention. In a 
preferred embodiment of this invention, the insecticidal compositions will 
comprise from about 5 to 75 percent by weight of the active compound. The 
compositions can also comprise such additional substances as other 
pesticides, stabilizers, spreaders, deactivators, adhesive, stickers, 
fertilizers, activators, synergists and the like. 
The compounds of the present invention are also useful when combined with 
other insecticides in the insecticidal compositions heretofore described. 
These other insecticides can comprise from about 5 to about 95 percent of 
the active ingredients in the insecticidal compositions. Use of the 
combinations of these other insecticides with the compounds of the present 
invention provide insecticidal compositions which are more effective in 
controlling insects and often provide results unattainable with separate 
compositions of the individual insecticides. The other insecticides with 
which the compounds of this invention can be used in the insecticidal 
compositions to control insects, can include halogenated compounds such as 
DDT, methoxychlor, TDE, lindane, chlordane, isobenzan, aldrin, dieldrin, 
heptachlor, endrin, mirex, endosulfon, dicofol and the like; organic 
phosphorus compounds such as TEPP, ethion, parathion, methyl parathion, 
EPN, demeton, carbophenothion, phorate, zinophos, diazinon, malathion, 
mevinphos, dimethoate, DBD, ronnel, oxydemeton-methyl, dicapthon, 
chlorothion, phosphamidon, naled, fenthion, trichlorofon, DDVP and the 
like; organic nitrogen compounds such as dinitro-o-cresol, 
dinitrocyclohexylphenol, DNB, DNP, binapacril, azobenzene and the like; 
organic carbamate compounds such as carbaryl, ortho 5353 and the like; 
organic sulfur compounds such as phenothiazine, phenoxathin, lauryl 
thiocyanate, bis(2-thiocyanoethyl)ether, isobornyl thiocyanoacetate and 
the like; as well as such substances usually referred to as fumigants, as 
hydrogen cyanide, carbon tetrachloride, calcium cyanide, carbon disulfide, 
ethylene dichloride, propylene dichloride, ethylene dibromide, ethylene 
oxide, methyl bromide, paradichlorobenzene and the like. 
The compounds of the present invention can also be combined with fungicidal 
and nematocidal chemical compounds to form pesticidal compositions useful 
for the control of fungi and in some cases soil nematodes as well as 
insects. Typical examples of such fungicidal chemical compounds are 
ferbam, nabam, zineb, ziram, thiram chloranil, dichlone, glyodin, 
cycloheximide, dinocap, maneb, captan, dodine, PCNB, 
p-dimethylaminobenzenediazo sodium sulfonate and the like; while examples 
of nematocidal compounds are chloropicrin, O,O-diethyl 
O-(2,4-dichlorophenyl) phosphorothioate, tetrachlorothiophene, dazomet, 
dibromochloropropane and the like. 
The new compounds of this invention can be used in many ways for the 
control of insects. Insecticides which are to be used as stomach poisons 
or protective materials can be applied to the surface on which the insects 
feed or travel. Insecticides which are to be used as contact poisons or 
eradicants can be applied directly to the body of the insect, as a 
residual treatment to the surface on which the insect may walk or crawl, 
or as a fumigant treatment of the air which the insect breathes. In some 
cases, the compounds applied to the soil or plant surfaces are taken up by 
the plant, and the insects are poisoned systemically. 
The above methods of using insecticides are based on the fact that almost 
all the injury done by insects is a direct or indirect result of their 
attempts to secure food. Indeed, the large number of destructive insects 
can be classified broadly on the basis of their feeding habits. Among the 
insects which can be effectively controlled by the compounds of the 
present invention are the chewing insects, such as the Mexican bean beetle 
and the southern armyworm; the piercing-sucking insects, such as the pea 
aphid, the cereal leaf beetle, the housefly, the grape leafhopper, the 
chinch bug, the lygus bug, the oyster shell scale, the California red 
scale, the Florida red scale, the soft scale and mosquitoes; the internal 
feeders, including borers, such as the European corn borer, the peach twig 
border and the corn earworm, worms or weevils, such as the codling moth, 
the alfalfa weevil, the cotton boll weevil, the pink boll worm, the plum 
curculio, the red banded leaf roller, the melonworm, the cabbage looper 
and the apple maggot, leaf miners such as the apple leaf miner, the birch 
leaf miner and the beet leaf miner, and gall insects such as the wheat 
joint worm and the grape phylloxera. Insects which attack below the 
surface of the ground are classified as subterranean insects and include 
such destructive pests as the wooly apple aphid, the Japanese beetle, the 
onion maggot and the corn rootworm. 
The quantity of active compound of this invention to be used for insect 
control will depend on a variety of factors, such as the specific insect 
involved, intensity of the infestation, weather, type of environment, type 
of formulation and the like. For example, the application of only one or 
two ounces of active chemical per acre may be adequate for control of a 
light infestation of an insect under conditions unfavorable for its 
feeding, while a pound or more of active compound per acre may be required 
for the control of a heavy infestation of insects under conditions 
favorable to their development. 
The insecticidal activity of the compounds of the present invention was 
demonstrated by experiments carried out for the control of a variety of 
insects. 
Housefly 
Approximately 25 to 30 four-day-old Housefly adults are placed in spherical 
wire mesh cages. The cages are mounted at the center of a rotating 
turntable so that each cage rotates on its own axis. At least three cages 
are provided for each test unit. Individual rotating cages are sprayed 
with aerosol formulations of the test compound at the indicated 
concentrations. Houseflies are then immediately removed to observation 
cages, observed for 60-minute knockdown, supplied sugar-water food source, 
transferred to a holding room and observed for mortality 24 hours after 
treatment. The results of this test are shown in Table I. 
TABLE I 
______________________________________ 
Test Rate Percent Control 
Compound 
(ppm): 1024 512 256 128 64 32 16 8 
______________________________________ 
Product of 
k -- $0 10 0 0* 0 0 0 
Example 3 
m -- 60 40 30 0* 0 0 0 
Product of 
k 100 100 70 40 0 0 0 0 
Example 6 
m 100 80 100 100 10 0 0 10 
Product of 
k -- 100 100 70 25* 0 0 0 
Example 9 
m -- 100 100 100 60* 0 0 0 
Product of 
k 100 90 60 40 -- -- -- -- 
Example 29 
m 100 90 60 40 -- -- -- -- 
Product of 
k 100 100 100 30 0 10 0 0 
Example 30 
m 100 100 100 90 90 30 20 0 
Product of 
k 100 100 90 40 20 -- -- -- 
Example 31 
m 100 100 100 40 50 -- -- -- 
Product of 
k 100 100 0 0 70 -- -- -- 
Example 32 
m 100 100 90 90 70 -- -- -- 
Product of 
k 100 100 100 100 40 -- -- -- 
Example 33 
m 100 90 20 70 0 -- -- -- 
______________________________________ 
k=60-minute knockdown 
m=24-hour mortality 
*Values are averages of two replicates. 
Southern Armyworm 
Foliar portions of potted Dwarf Horticultural bean plants in first true 
leaf growth stage are sprayed with test solution containing a compound of 
this invention. The pots are then placed in holding racks provided with a 
subterranean water source. Three test plants are used for each test unit. 
Five third-instar larvae of Southern Armyworm are caged on treated plants 
for 48 hours. After this time observations are made for insect mortality. 
The results of this procedure are set forth in Table II. 
TABLE II 
______________________________________ 
Test Percent Control 
Compound Rate (ppm): 
1024 512 256 128 64 
______________________________________ 
Product of 
Example 3 -- 10 0 0 0 
Product of 
Example 6 0 0 0 0 -- 
Product of 
Example 9 -- 0 0 0 0 
Product of 
Example 29 0 0 0 0 -- 
Product of 
Example 30 0 30 10 30 0 
Product of 
Example 31 0 0 0 0 0 
Product of 
Example 32 20 10 10 30 -- 
Product of 
Example 33 100 80 0 0 0 
______________________________________ 
Mexican Bean Beetle 
Foliar portions of potted Dwarf Horticultural bean plants in first true 
leaf growth stage are sprayed with test solution containing a compound of 
this invention, and in some cases the soil of the potted plants is also 
drenched with an aqueous emulsion of the test compound. The pots are then 
placed in holding racks provided with a subterranean water source. Three 
test plants are used for each test unit. Five third-instar larvae of 
Mexican Bean Beetle are caged on treated plants for 48 hours. After this 
time observations are made for insect mortality. The results of these 
experiments are summarized in Table III. 
TABLE III 
______________________________________ 
Percent Control 
Test Rate (ppm) 
Compound 1024 512 256 128 64 32 16 8 
______________________________________ 
Product of 
Example 3 
-- 0 0 0 10 -- -- -- 
+64 #/acre 
soil drench 
-- 10 0 10 20 -- -- -- 
Product of 
Example 6 
10 10 10 0 -- -- -- -- 
Product of 
Example 9 
-- 30 20 10 0 -- -- -- 
Product of 
Example 29 
50 30 10 0 -- -- -- -- 
Product of 
Example 30 
100 100 100 90 100 20 20 10 
Product of 
Example 31 
100 100 100 90 70 -- -- -- 
Product of 
Example 32 
80 90 90 30 0 -- -- -- 
Product of 
Example 33 
100 100 100 90 100 90 80 50 
______________________________________ 
Boll Weevil 
Two leaves of a cotton plant are sprayed with test solution containing a 
compound of this invention at the indicated rates and are allowed to air 
dry. Boll weevils are then placed on the surface of the leaves, and the 
infested leaves are kept in a petri dish and are held for a period of 48 
hours. After this time mortality is observed and compared to untreated 
controls. The results of these tests are shown in Table IV. 
TABLE IV 
______________________________________ 
Percent Control 
Test Rate (ppm) 
Compound 1024 512 256 128 64 32 16 8 
______________________________________ 
Product of 
Example 3 
-- 80 50 40 30 -- -- -- 
Product of 
Example 6 
-- 0 10 0 0 -- -- -- 
Product of 
Example 9 
-- 40 20 20 10 -- -- -- 
Product of 
Example 29 
0 0 0 0 -- -- -- -- 
Product of 
Example 30 
10 30 20 10 10 -- -- -- 
Product of 
Example 31 
40 30 20 20 20 20 10 10 
Product of 
Example 32 
0 10 10 30 -- -- -- -- 
Product of 
Example 33 
70 50 40 30 20 -- -- -- 
______________________________________ 
Two-Spotted Spider Mite 
Potted horticultural beans at growth stage when primary leaves are 
approximately one inch long are infested with two-spotted spider mites 24 
hours prior to treatment, ensuring establishment of adults and egg 
deposition at time of treatment. 
The candidate compound is dissolved in a suitable solvent (acetone, 
methanol or other) or prepared as a wettable powder and diluted to 
appropriate concentrations with deionized water containing wetting and/or 
dispersing agents as appropriate. 
Infested host plants, as above, are sprayed with test solution containing a 
compound of this invention. The pots are then placed in holding racks 
provided with a subterranean water source. Mortality is determined 48 
hours after treatment by removing and observing one leaf from each plant. 
The results of these tests are set forth in Table V. 
TABLE V 
______________________________________ 
Percent Control 
Test Rate (ppm) 
Compound 1024 512 256 128 64 
______________________________________ 
Product of 
Example 3 0 0 0 0 -- 
Product of 
Example 9 80 60 0 0 -- 
Product of 
Example 29 30 20 0 0 -- 
Product of 
Example 30 85 88 90 80 83 
Product of 
Example 31 85 84 90 80 0 
Product of 
Example 32 92 96 90 80 20 
Product of 
Example 33 95 90 60 50 20 
______________________________________ 
Cabbage Looper 
Ten- to fourteen-day-old Henderson bush lima bean plants are planted in 
31/2" plastic pots using potting soil capped with 1/4" of sand. The bean 
plants are then placed on a turntable and are sprayed with 100 ml of an 
aqueous solution or dispersion of a compound of this invention at the 
indicated concentrations. The plants are allowed to dry, and a leaf is 
removed from each and placed in a petri dish on top of a piece of wetted 
filter paper. Ten third-instar larvae of the Cabbage Looper are then 
placed on the leaf, and the petri dish is covered. Observations of 
mortality are made after 48 hours and are compared to untreated controls. 
Results of these tests are shown in Table VI. 
TABLE VI 
______________________________________ 
Test Percent Control 
Compound Rate (ppm): 
1024 512 256 128 64 
______________________________________ 
Product of 
Example 3 -- 70 50 30 10 
Product of 
Example 6 30 0 0 10 -- 
Product of 
Example 9 -- 100 90 80 80 
Product of 
Example 29 0 0 0 0 -- 
Product of 
Example 30 60 -- -- -- 10 
Product of 
Example 31 30 -- -- -- 10 
Product of 
Example 32 20 10 10 10 30 
______________________________________ 
Yellow Fever Mosquito Larvae 
Aliquots of 100 ml of tap water containing various concentrations of 
compounds of this invention are each supplied with 20 1-day-old Yellow 
Fever Mosquito larvae (Aedes aegypti L.). The larvae are maintained at 
25.degree. C. and are fed with malt yeast powder. After 13 days, when the 
pupae of untreated insects have hatched, the mortality percentages are 
calculated in comparison with the untreated controls. The results are 
indicated in Table VII. 
TABLE VII 
______________________________________ 
Percent Control 
Test Rate (ppm): 
Compound 512 128 32 10 8 2 1 0.1 0.01 
______________________________________ 
Product of 
Example 3 100 80 60 80 10 0 70 50 30 
Product of 
Example 6 -- -- -- 100 -- -- 40 0 0 
Product of 
Example 9 100 100 100 100 50 30 70 20 0 
Product of 
Example 29 
-- -- -- 100 -- -- 40 0 0 
Product of 
Example 30 
-- -- -- 20 -- -- 10 10 10 
Product of 
Example 31 
-- -- -- 40 -- -- 20 0 0 
Product of 
Example 32 
-- -- -- 10 -- -- 10 0 0 
Product of 
Example 33 
-- -- -- 100 -- -- 90 60 40 
______________________________________ 
Pea Aphid 
Windsor Broad Bean plants grown under greenhouse conditions, in the first 
true leaf growth stage and in soil of low moisture content are sprayed 
with test solution containing a compound of this invention. The pots are 
then placed in holding racks provided with a subterranean water source. 
Adult pea aphids are transferred to the foliar portion of the treated 
plants and held there for a period of 48 hours. After this time insect 
mortality is determined by observation in comparison to controls. The 
results of these procedures are shown in Table VIII. 
TABLE VIII 
______________________________________ 
Test Percent Control 
Compound Rate (ppm): 
1024 512 256 128 64 
______________________________________ 
Product of 
Example 3 35 35 20 10 -- 
Product of 
Example 6 100 100 100 90 -- 
Product of 
Example 9 80 60 60 50 -- 
Product of 
Example 29 70 40 0 0 -- 
Product of 
Example 30 0 0 0 0 -- 
Product of 
Example 31 0 0 0 0 -- 
Product of 
Example 32 0 0 0 0 -- 
Product of 
Example 33 100 100 50 25 0 
______________________________________ 
Green Peach Aphid 
Dwarf Masturtiums are planted in 31/2" plastic pots containing potting soil 
capped with 1/4" of sand. Ten- to fourteen-day-old plants are placed on a 
revolving table in a mist chamber and sprayed with 100 ml of a solution 
containing a compound of this invention at the indicated concentrations. 
After the leaves have dried, an untreated leaf infested with 10 to 20 
Green Peach Aphids is placed on a treated leaf. As the untreated leaf 
wilts, the aphids crawl onto the treated leaf. Mortality is recorded in 
comparison to untreated controls 48 hours after infestation of the treated 
plant. The results of these tests are set forth in Table IX. 
TABLE IX 
______________________________________ 
Percent Control 
Test Rate (ppm) 
Compound 1024 512 256 128 64 32 16 8 
______________________________________ 
Product of 
Example 3 35 0 0 0 -- -- -- -- 
Product of 
Example 6 100 100 100 80 -- -- -- -- 
Product of 
Example 9 100 100 75 10 -- -- -- -- 
Product of 
Example 29 
0 0 0 0 -- -- -- -- 
Product of 
Example 30 
96 85 40 40 30 -- -- -- 
Product of 
Example 31 
100 100 90 75 0 -- -- -- 
Product of 
Example 32 
100 90 80 60 75 -- -- -- 
Product of 
Example 33 
90 90 50 25 0 100 40 10 
______________________________________ 
German Cockroach 
Ten adult German cockroaches are first anesthetized with carbon dioxide and 
thereafter dipped into a 100 ml solution of the test compound at the 
indicated concentrations. Thereafter the cockroaches are placed in holding 
cups and supplied with water as required. Mortality of the roaches is 
observed 48 hours after treatment in comparison to untreated controls. The 
results of these tests are shown in Table X. 
TABLE X 
______________________________________ 
Test Percent Control 
Compound Rate (ppm): 
1024 512 256 128 
______________________________________ 
Product of 
Example 3 20 10 10 0 
Product of 
Example 6 100 40 10 0 
Product of 
Example 9 70 20 10 0 
______________________________________ 
The systemic activity of the compounds of the present invention was 
demonstrated in experiments wherein the test compounds were applied as 
soil drenches. In the soil drench applications fourteen-day-old cotton 
plants or bean plants are watered with 25 ml of a solution of the test 
compound at the indicated rates. After 48 hours the primary leaves are 
removed and placed in a closed container with the insect species. For 
those species of insects which do not leave their host plants the insects 
are placed on the growing plants. In each instance forty-eight hours after 
infestation mortality was observed and compared to untreated controls. The 
results of these tests are shown in Table XI. 
TABLE XI 
__________________________________________________________________________ 
SOIL DRENCH 
Rate #/A 
Product of 
Insect Percent Control 
Examples: 
Species 
64 32 16 8 4 2 1 .5 
__________________________________________________________________________ 
30 SAW 10 -- -- -- -- -- -- -- 
" MBB 30 -- -- -- -- -- -- -- 
" TSM 50 -- -- -- -- -- -- -- 
" CAL 20 -- -- -- -- -- -- -- 
" GPA 60 -- -- -- -- -- -- -- 
" SCR 24h 
-- -- 80 80 
80 60 40 -- 
48h 
-- -- 100 
100 
100 
80 60 -- 
31 SAW 20 -- -- -- -- -- -- -- 
" MBB 90 100 
90 100 
30 10 10 -- 
" TSM 60 40 
20 0 -- -- -- -- 
" CAL 20 -- -- -- -- -- -- -- 
" PA -- -- -- -- 80 60 50 0 
" GPA 100 
100 
100 
90 
90 50 40 -- 
" SCR 24h 
-- -- 80 80 
60 40 20 -- 
48h 
-- -- 100 
100 
100 
80 60 -- 
32 SAW 30 -- -- -- -- -- -- -- 
" MBB 30 -- -- -- -- -- -- -- 
" BW 0 -- -- -- -- -- -- -- 
" TSM 0 -- -- -- -- -- -- -- 
" CAL 10 -- -- -- -- -- -- -- 
" GPA 50 -- -- -- -- -- -- -- 
" SCR 24h 
-- -- 100 
100 
100 
80 40 -- 
48h 
-- -- 100 
100 
100 
100 
60 -- 
33 SAW 0 -- -- -- -- -- -- -- 
" MBB 100 
90 
80 40 
20 -- -- -- 
" BW 10 -- -- -- -- -- -- -- 
" TSM 50 -- -- -- -- -- -- -- 
" PA 80 85 
30 0 0 -- -- -- 
" GPA 90 100 
86 60 
50 -- -- -- 
" SCR 24h 
-- -- -- 0 40 0 0 20 
72h 
-- -- -- 100 
100 
100 
100 
40 
__________________________________________________________________________