N-haloalkanesulfenylcarbamoyloxime compositions have been found to have exceptional miticidal and insecticidal activity.

This invention relates to novel compositions of matter and to their use in 
combating insects and mites. 
The compounds which are employed as the active ingredients in the 
pesticidal compositions of this invention are new compounds corresponding 
to the following general formula: 
##STR1## 
wherein: 
R is: 
A. lower alkyl; 
B. lower alkyl substituted with one or more lower alkoxy, lower alkylthio, 
lower alkylsulfinyl, lower alkylsulfonyl, phenylthio, phenylsulfinyl, 
phenylsulfonyl or R.sub.4 CON(R.sub.5)--, all of which may be substituted 
with one or more cyano, nitro, azido, chloro, bromo or fluoro 
substituents; 
R.sub.1 is: 
A. hydrogen, chlorine, bromine, fluorine, cyano; 
B. alkyl having from 1 to 4 carbon atoms, lower alkylthio, lower alkoxy, 
lower carboalkoxyalkylthio, lower alkylthioalkyl, all of which may either 
unsubstituted or substituted with one or more chloro, bromo, fluoro cyano 
or nitro groups. 
R.sub.2 is lower alkyl or lower alkyl substituted with one or more chloro, 
bromo, fluoro, nitro cyano, lower alkoxy or lower alkyl groups; 
R.sub.3 is perhalomethanesulfenyl or perhaloethanesulfenyl wherein the 
permissible halogen substituents are chloro, bromo or fluoro; 
R.sub.4 and R.sub.5 are individually hydrogen or lower alkyl; with the 
proviso that 
A. when R is alkyl, R.sub.1 is substituted lower alkyl, substituted lower 
alkylthio, unsubstituted or substituted lower alkoxy, unsubstituted or 
substituted lower carboalkoxyalkylthio or unsubstituted or substituted 
lower alkylthioalkyl; 
B. when R.sub.1 is hydrogen, R is other than unsubstituted lower 
alkylthioalkyl; and 
C. at least one of the groups R, R.sub.1 and R.sub.2 is a group including 
one or more cyano substituents when R.sub.1 is other than cyano. 
Compositions including these compounds as the active ingredient, are useful 
in combating insects and mites. In general, the compositions having the 
greatest degree of pesticidal activity are those in which the combined 
total number of aliphatic carbon atoms in the ennumerated substituents 
does not exceed about 10 carbon atoms. 
The preferred compositions of this invention are those in which R.sub.2 is 
methyl and R.sub.3 perhalomethanesulfenyl. 
It will be appreciated that the active compounds of this invention will 
exist in at least two isomeric forms. In the "syn" configuration, the 
oxygen atoms of the oximino function is on the same side of the oximino 
double bond as the R substituent in the generic formula set forth above 
while in the "anti" configuration, the pg,6 oxygen atom is on the 
opposite side of the oximino function. Both isomers are within the scope 
of our invention, however the syn isomers are preferred due to their 
greater biological activity. 
The novel compounds of this invention in comparison to the corresponding 
N-methylcarbamate compounds, some of which are well known insecticides, 
have been found to possess essentially equivalent insecticidal and 
miticidal activity although in some cases enhanced activity against 
particular pests have been observed. Surprisingly, however, the compounds 
of this invention demonstrate a sharp reduction in mammalian toxicity as 
compared to the N-methyl compounds. In addition nearly all of the novel 
compositions of this invention are quite stable under normal conditions 
and can be stored for long periods of time without appreciable loss or 
reduction in biological activity. This is to be contrasted with many of 
the corresponding N-methyl carbamate compositions which are relatively 
unstable and can not be stored for any appreciable length of time and as 
such are not useful pesticides because of practical considerations. 
Compositions which exhibit the greatest stability, and generally enhanced 
pesticidal activity are those in which the cumulative sigma* value of the 
groups R and R.sub.1 of the active compound is at least 1.1. 
This problem of instability is particularly acute in the case of compounds 
of the type described above wherein R.sub.1 is hydrogen if there is not 
present a relatively strong electron withdrawing function in the R 
substituent. Certain compounds, such as those in which R.sub.1 is hydrogen 
and R is alkylthio are unstable despite the relatively strong electron 
withdrawing character of the alkylthio substituent. These compounds are 
not included within the scope of the generic formula as defined above. 
The active compounds of this invention can be prepared conveniently in 
accordance with the following general reaction scheme: 
##STR2## 
where R, R.sub.1, R.sub.2 and R.sub.3 are as described above and where X 
is either chlorine or fluorine. 
The oxime precursors used in the preparation of the active compounds of 
this invention can be prepared by conventional means as for example by the 
methods described in U.S. Pat. Nos. 3,217,036, 3,217,037, 3,400,153, 
3,536,760 and 3,576,834. 
The carbamic acid fluoride precursor compounds can be prepared by the 
method described in U.S. Pat. No. 3,769,471. The carbamic acid chloride 
compounds can be prepared by the method described in Belgium Pat. No. 
796,646. 
The reaction between the oxime compound and the carbamic acid halid 
compound is preferably carried out in an aprotic solvent and in the 
presence of a base. The preferred base materials are tertiary amines and 
alkaline earth bases. Yields obtained by this reaction are generally 
quantitative.

The following specific examples are presented to more particularly 
illustrate the manner in which the active compounds of this invention may 
be prepared. 
EXAMPLE I 
To a solution of 2.26 g (0.0111 m) 
N-methyl-N-trichloromethanesulfenylcarbamyl fluoride and 1.29 (0.011 m) 
2-methyl-2-cyanopropionaldehydeoxime in 75 ml dioxane was added dropwise 
with stirring 1.28 g (0.013 m) triethylamine. The spontaneous exotherm 
raised the temperature from 23.degree. to 29.degree. C. After stirring for 
an additional period of 0.5 hr at ambient temperature, the reaction 
mixture was quenched with 300 ml of water. The product was extracted into 
ethylene acetate and the resulting solution was dried over magnesium 
sulfate and concentrated to a residual oil which crystallized from 
isopropyl ether to yield 2.0 g of the desired product 
2-methyl-2-cyanopropionaldehyde-(N-methyl-N-trichloromethanesulfenylcarbam 
oyl)oxime mp 105.degree.-107.degree. C. Recrystallization raised the mp to 
111.degree.-113.degree. C. 
Analysis - Calcd. for C.sub.8 H.sub.10 N.sub.3 O.sub.2 Cl.sub.3 S: C, 
30.16; H, 3.16; N, 13.19 Found: C, 30.15; H, 3.29; N, 13.36 
EXAMPLE II 
To a solution of 1.1 g (0.008 m) 1-(2-cyanoethylthio)acetaldoxime, and 1.8 
g (0.008 m) N-methyl-N-(trichloromethanesulfenylcarbamoyl) fluoride in 50 
ml of dioxane was added dropwise with stirring at 28.degree.-30.degree. C, 
0.9 g of triethylamine. After stirring overnight at ambient temperature, 
the reaction mixture was poured in 500 ml of water and stirred for 10 
minutes. The precipitated solid was washed with water and dried. On 
recrystallization from isopropanol it yielded 1.1 g of 
1-(2-cyanoethylthio)acetaldehyde-(N-methyl-N-trichloromethanesulfenylcarba 
moyl)oxime, mp 136.degree.-138.degree. C. 
The following compositions in addition to those described in the above 
examples are illustrative of the new compositions of this invention: 
2-Phenylthio-1-cyanoacetaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
1-(2-Cyanopropylthio)acetaldehyde O 
-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
1-(2-Cyanomethylthio)acetaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Cyano-2-methyl-1-(2-cyanoethylthio)propionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Nitro-2-methyl-1-(2-cyanoethylthio)propionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
3-Methyl-3-cyanobutanone-2O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)o 
xime. 3-Cyanobutanone-2 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-cyanopropionaldehyde O 
-(N-methyl-N-trifluoromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-(N-methyl-N-fluorodichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-(cyanoethyl)thiopropionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-methoxy-1-cyanopropionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-methylthio-1-cyanopropionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Cyano-2-methyl-1-methylthiopropionaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
1-(2-Cyanoethylthio)acetaldehyde 
O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
1-(2-cyanoethylthio)acetaldehyde 
O-(N-methyl-N-trifluoromethanesulfenylcarbamoyl)oxime. 
1-(2-cyanoethylthio)acetaldehyde 
O-(N-methyl-N-fluorodichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-[N-(2-chloroethyl)-N-trichloromethanesulfenylcarbamoyl]oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-[N-(n-propyl)-N-dichlorofluoromethanesulfenylcarbamoyl]oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-[N-(2-nitroethyl)-N-trichloromethanesulfenylcarbamoyl]oxime 
2-Methyl-2-cyanopropionaldehyde 
O-(N-cyanomethyl-N-trichloromethanesulfenylcarbamoyl)oxime. 
2-Methyl-2-cyanopropionaldehyde 
O-(N-vinyl-N-trichloromethanesulfenylcarbamoyl)oxime 
2-Methyl-2-cyanopropionaldehyde 
O-(N-benzyl-N-trichloromethanesulfenylcarbamoyl)oxime 
2-Methyl-2-cyanopropionaldehyde 
O-(N-phenyl-N-trichloromethanesulfenylcarbamoyl)oxime 
2-Methyl-2-cyanopropionaldehyde 
O-[N-(4-chlorophenyl)-N-trichloromethanesulfenylcarbamoyl] 
2-Methyl-2-cyanopropionaldehyde 
O-[N-(4-methoxyphenyl)-N-trichloromethanesuflenylcarbamoyl]oxime 
Selected species of the new compounds were evaluated to determine their 
pesticidal activity against mites, nematodes and certain insects, 
including an aphid, a caterpillar, a beetle and a fly. 
Suspensions of the test compounds were prepared by dissolving one gram of 
compound in 50 milliliters of acetone in which had been dissolved 0.1 gram 
(10 percent of the weight of compound) of an alkylphenoxy 
polyethoxyethanol surfactant, as an emulsifying or dispersing agent. The 
resulting solution was mixed into 150 milliliters of water to give roughly 
200 milliliters of a suspension containing the compound in finely divided 
form. The thus-prepared stock suspension contained 0.5 percent by weight 
of compound. The test concentrations in parts per million by weight 
employed in the tests described hereinbelow were obtained by appropriate 
dilutions of the stock suspension with water. The test procedures were as 
follows: 
Bean Aphid Foliage Spray Test 
Adults and nymphal stages of the bean aphid (Aphis fabae Scop.) reared on 
potted dwarf nasturtium plants at 65.degree.-70.degree. F. and 50-70 
percent relative humidity, constituted the test insects. For testing 
purposes, the number of aphids per pot was standardized to 100-150 by 
trimming plants containing excess aphids. 
The test compounds were formulated by diluting the stock suspension with 
water to give a suspension containing 500 parts of test compound per 
million parts of final formulation. 
The potted plants (one pot per compound tested) infested with 100-150 
aphids, were placed on a revolving turntable and sprayed with 100-110 
milliliters of test compound formulation by use of a DeVilbiss spray gun 
set at 40 psig. air pressure. This application, which lasted 25 seconds, 
was sufficient to wet the plants to run-off. As a control, 100-110 
milliliters of a water-acetone-emulsifier solution containing no test 
compound were also sprayed on infested plants. After spraying, the pots 
were placed on their sides on a sheet of white standard mimeograph paper 
which had been previously ruled to facilitate counting. Temperature and 
humidity in the test room during the 24 hour holding period were 
65.degree.-70.degree. F. and 50-70 percent, respectively. Aphids which 
fell onto the paper and were unable to remain standing after being 
uprighted were considered dead. Aphids remaining on the plants were 
observed closely for movement and those which were unable to move the 
length of the body upon stimulation by prodding were considered dead. 
Percent mortality was recorded for various concentration levels. 
Southern Armyworm Leaf Spray Test 
Larvae of the southern armyworm (Prodenia eridania, (Cram.)), reared on 
Tendergreen bean plants at a temperature of 80.+-.5.degree. F. and a 
relative humidity of 50.+-.5 percent, constituted the test insects. 
The test compounds were formulated by diluting the stock suspension with 
water to give a suspension containing 500 parts of test compound per 
million parts of final formulation. Potted Tendergreen bean plants of 
standard height and age were placed on a revolving turntable and sprayed 
with 100-110 milliliters of test compound formulation by use of a 
DeVilbiss spray gun set at 10 psig air pressure. This application, which 
lasted 25 seconds, was sufficient to wet plants to run-off. As a control, 
100-110 milliliters of a water-acetone-emulsifier solution containing no 
test compound were also sprayed on infested plants. When dry, the paired 
leaves were separated and each one was placed in a 9 centimeter Petri dish 
lined with moistened filter paper. Five randomly selected larvae were 
introduced into each dish and the dishes were closed. The closed dishes 
were labeled and held at 80.degree.-85.degree. F. for 3 days. Although the 
larvae could easily consume the whole leaf within twenty-four hours, no 
more food was added. Larvae which were unable to move the length of the 
body, even upon stimulation by prodding, were considered dead. Percent 
mortality was recorded for various concentration levels. 
Mexican Bean Beetle Leaf Spray Test 
Fourth instar larvae of the Mexican bean beetle (Epilachna varivestis, 
Muls.), reared on Tendergreen bean plants at a temperature of 
80.+-.5.degree. F. and 50.+-.5 percent relative humidity, were the test 
insects. 
The test compounds were formulated by diluting the stock suspension with 
water to give a suspension containing 500 parts of test compound per 
million parts of final formulation. Potted Tendergreen bean plants of 
standard height and age were placed on a revolving turntable and sprayed 
with 100-110 milliliters of test compound formulation by use of a 
DeVilbiss spray gun set at 10 psig air pressure. This application, which 
lasted 25 seconds, was sufficient to wet plants to run-off. As a control, 
100-110 milliliters of a water-acetone-emulsifier solution containing no 
test compound were also sprayed on infested plants. When dry, the paired 
leaves were separated and each was placed in a 9 centimeter Petri dish 
lined with moistened filter paper. Five randomly selected larvae were 
introduced into each dish, and the dishes were closed. The closed dishes 
were labeled and held at a temperature of 80.+-.5.degree. F. for 3 days. 
Although the larvae could easily consume the leaf within 24 to 48 hours, 
no more food was added. Larvae which were unable to move the length of the 
body, even upon stimulation, were considered dead. 
Fly Bait Test 
Four to six day old adult house flies (Musca domestica, L.), reared 
according to the specifications of the Chemical Specialities Manufacturing 
Association (Blue Book, McNair-Dorland Co., N.Y. 1954; pages 243-244, 261) 
under controlled conditions of 80.+-.5.degree. F. and 50.+-.5 percent 
relative humidity, were the test insects. The flies were immobilized by 
anesthetizing with carbon dioxide and twenty five immobilized individuals, 
males and females, were transferred to a cage consisting of a standard 
food strainer about five inches in diameter which was inverted over a 
wrapping-paper-covered surface. The test compounds were formulated by 
diluting the stock suspension with a 10 percent (by weight) sugar solution 
to give a suspension containing 500 parts of test compound per million 
parts of final formulation, by weight. Ten milliliters of the test 
formulation were added to a souffle cup containing a one-inch square of an 
absorbent cotton pad. This bait cup was introduced and centered on the 
blotting paper under the food strainer prior to admitting the anesthetized 
flies. The caged flies were allowed to feed on the bait for 24 hours, at a 
temperature of 80.+-.5.degree. F. and the relative humidity of 50.+-.5 
percent. Flies which showed no sign of movement on prodding were 
considered dead. 
Mite Foliage Spray Test 
Adults and numphal stages of the two-spotted mite (Tetranychus urticae 
Koch), reared on Tendergreen bean plants at 80.+-.5 percent relative 
humidity, were the test organisms. Infested leaves from a stock culture 
were placed on the primary leaves of two bean plants six to eight inches 
in height, growing in a two-and-a-half inch clay pot. 150-200 Mites, a 
sufficient number for testing, transferred from the excised leaves to the 
fresh plants in a period of twenty four hours. Following the twenty four 
hour transfer period, the excised leaves were removed from the infested 
plants. The test compounds were formulated by diluting the stock 
suspension with water to give a suspension containing 500 parts of test 
compound per million parts of final formulation. The potted plants (one 
pot per compound) were placed on a revolving turntable and sprayed with 
100-110 milliliters of test compound formulation by use of a DeVilbiss 
spray gun set at 40 psig. air pressure. This application, which lasted 25 
seconds, was sufficient to wet the plants to run-off. As a control, 
100-110 milliliters of a water solution containing acetone and emulsifier 
in the same concentrations as the test compound formulation, but 
containing no test compound, were also sprayed on infested plants. The 
sprayed plants were held at 80.+-.5 percent relative humidity for 6 days, 
after which a mortality count of motile forms was made. Microscopic 
examination for motile forms was made on the leaves of the test plants. 
Any individual which was capable of locomotion upon prodding was 
considered living. 
MITE SYSTEMIC TEST 
Systemic treatments were made by drenching 20 milliliters of the test 
compound formulation into the soil around the roots of bean plants growing 
in 21/2 inch clay pots. These pots were held in 4 ounce wax paper 
containers to prevent cross-contamination and loss by leaching. The plants 
were 4 inches high at the time of treatment and had been infested with 
mites 24 hours previously. Subsequent steps for testing of the systemic 
miticidal activity were the same as those described above for the spray 
method of application. 
NEMATOCIDE TEST 
The test organism used was the infective migratory larvae of the root-knot 
nematode, Meloidogyne incognita var. acrita, reared in the greenhouse on 
roots of cucumber plants. Infected plants were removed from the culture, 
and the roots are chopped very finely. A small amount of this inoculum was 
added to a pint jar containing approximately 180 cc. of soil. The jars 
were capped and incubated for one week at room temperature. During this 
period eggs of the nematode were hatched, and the larval forms migrated 
into the soil. 
Ten ml. of the test formulation were added to each of the two jars for each 
dosage tested. Following the addition of chemical, the jars were capped, 
and the contents thoroughly mixed on a ball mill for 5 minutes. 
The test compounds were formulated by a standard procedure of solution in 
acetone addition of an emulsifier, and dilution with water. Primary 
screening tests were conducted at 3.33 m.g. of the test compound per jar. 
The jars were left capped at room temperature for a period of 48 hours, and 
the contents then transferred to 3 inch pots. Subsequently, the pots were 
seeded to cucumber as an indicator crop and placed in the greenhouse where 
they were cared for in the normal fashion for approximately 3 weeks. 
The cucumber plants were then taken from the pots, the soil removed from 
the roots, and the amount of galling visually rated. 
In the tests described above, the pesticidal activity of the compounds 
against aphid, mite, Southern Armyworm, Bean Beetle, house fly and 
nematode was rated as follows: 
A = excellent control 
B = partial control 
C = no control 
Certain of these compositions were also evaluated to determine their 
peroral toxicity to mammals. The animal selected for this experiment was 
the rat. The test results obtained are expressed in terms of the number of 
milligrams of composition per kilogram of weight of the animal required to 
achieve a mortality rate of 50 percent (LD.sub.50). 
The results of these tests are set forth in Table I below: Dashes indicate 
no test conducted. 
TABLE I 
__________________________________________________________________________ 
Mite Mite Army- 
Structure m p c .degree. C 
Aphid 
(Spray) 
(Systemic) 
worm 
Beetle 
Fly 
Nematode 
Rat 
__________________________________________________________________________ 
##STR3## 111-113 
A A A A A A C -- 
##STR4## 74-76 A A A B A A C -- 
##STR5## 59-61 A A -- A A A A -- 
##STR6## 136-138 
A A -- A A A C 85.7 
__________________________________________________________________________ 
At higher dosage rates all of the above compositions may be expected to 
exhibit some activity against the various test species, however the data 
presented in Table I above clearly indicates a rather high degree of 
selectivity for some compositions and a broad spectrum of activity for 
others. 
It will be understood that the insect species employed in the above tests 
are merely representative of a wide variety of pests that can be 
controlled by use of my compounds. These compounds demonstrate systemic as 
well as contact toxicity against insects and mites. 
It should be noted that in addition to their insecticidal and miticidal 
activity, noteworthy nematocidal activity was also displayed by our 
compounds. 
Comparison tests were conducted to assess the biological and chemical 
properties of certain representative species of the claimed invention in 
relation to their corresponding N-methyl carbamate compositions. The test 
procedures described above were employed in these experiments in order to 
determine the LD.sub.50 (number of parts per million of active ingredients 
required to achieve fifty percent mortality of the insects tested) for 
each of the compositions tested. In the case of the aphid and mite tests a 
side by side comparison was made of the N-methyl carbamate composition 
versus the corresponding perhalomethylsulfenyl derivative. The results of 
these experiments are set forth in Table II below. 
TABLE II 
__________________________________________________________________________ 
COMATIVE BIOLOGICAL ACTIVITY OF CERTAIN UNSUB- 
N-METHYLCARBAMATE COMPOSITIONS -STITUTED N-METHYLCARBAMATE THEIR COR- 
RESPONDING SULFENYLATED DERIVATIVES (LD.sub.50 IN PPM 
##STR7## 
Mites 
Army- 
R X Stability 
Aphids 
Spray 
worm 
Beetle 
Housefly 
Rat 
__________________________________________________________________________ 
H CN (unstable) 
12 40 55 65 3 9.5 
SCCl.sub.3 
CN (stable) 
23 23 50 45 7 28.3 
SCF.sub.3 
CN (stable) 
38 90 300 40 14 -- 
##STR8## 
H -- (stable) 
8 8 5 25 2 7.7 
SCCl.sub.3 
-- (stable) 
10 22 6 15 3 85.7 
__________________________________________________________________________ 
These experimental results clearly demonstrate the remarkable reduction in 
mammalian toxicity achieved with the present compositions in comparison to 
their corresponding N-methylcarbamate derivatives as well as their 
improved chemical stability. 
The compounds contemplated in this invention may be applied as 
insecticides, miticides and nematocides according to methods known to 
those skilled in the art. Pesticidal compositions containing the compounds 
as the active toxicant will usually comprise a carrier and/or diluent, 
either liquid or solid. 
Suitable liquid diluents or carriers include water, petroleum distillates, 
or other liquid carriers with or without surface active agents. Liquid 
concentrates may be prepared by dissolving one of these compounds with a 
nonphytotoxic solvent such as acetone, xylene, or nitrobenzene and 
dispersing the toxicants in water with the aid of suitable surface active 
emulsifying and dispersing agents. 
The choice of dispersing and emulsifyng agents and the amount employed is 
dictated by the nature of the composition and the ability of the agent to 
facilitate the dispersion of the toxicant. Generally, it is desirable to 
use as little of the agent as is possible, consistent with the desired 
dispersion of the toxicant in the spray so that rain does not re-emulsify 
the toxicant after it is applied to the plant and wash it off the plant. 
Nonionic, anionic, or cationic dispersing and emulsifying agents may be 
employed, for example, the condensation products of alkylene oxides with 
phenol and organic acids, alkyl aryl sulfonates, complex ether alcohols, 
quaternary ammonium compounds, and the like. 
In the preparation of wettable powder or dust or granulated compositions, 
the active ingredient is dispersed in and on an appropriately divided 
solid carrier such as clay, talc, bentonite, diatomaceous earth, fullers 
earth, and the like. In the formulation of the wettable powders the 
aforementioned dispersing agents as well as lignosulfonates can be 
included. 
The required amount of the toxicants contemplated herein may be applied per 
acre treated in from 1 to 200 gallons or more of liquid carrier and/or 
diluent or in from about 5 to 500 pounds of inert solid carrier and/or 
diluent. The concentration in the liquid concentrate will usually vary 
from about 10 to 95 percent by weight and in the solid formulations from 
about 0.5 to about 90 percent by weight. Satisfactory sprays, dusts, or 
granules for general use contain from about 1/4 to 15 pounds of active 
toxicant per acre. 
The pesticides contemplated herein prevent attack by insects, mites and 
nematodes upon plants or other material to which the pesticides are 
applied, and they have relatively high residual toxicity. With respect to 
plants, they have a high margin of safety in that when used in sufficient 
amount to kill or repel the insects, they do not burn or injure the plant, 
and they resist weathering which includes wash-off caused by rain, 
decomposition by ultra-violet light, oxidation, or hydrolysis in the 
presence of moisture or, at least, such decomposition, oxidation, and 
hydrolysis as would materially decrease the desirable pesticidal 
characteristic of the toxicants or impart undesirable characteristics, for 
instance, phytotoxicity, to the toxicants. The toxicants are so chemically 
inert that they are now compatible with substantially any other 
constituents or the spray schedule, and they may be used in the soil, upon 
the seeds, or the roots of plants without injuring either the seeds or 
roots of plants. They may also be used in combination with other active 
ingredients such as miticides, insecticides and herbicides.