close

Вход

Забыли?

вход по аккаунту

?

Патент USA US3053735

код для вставки
United States Patent
3,053,729
CC
Patented Sept. 11, 1962
‘1
as amino, nitro and halogen. Each R" independently
represents hydrogen, halogen (preferably chlorine) or an
3,053,729
INSECTICIDAL COMPOSITIONS
Yun-Pei Sun, Modesto, Calif., assignor to Shell Oil
Company, a corporation of Delaware
' No Drawing. Filed Oct. 26, 1959, Ser. No. 848,499
5 Claims. (Cl. 167-22)
alkyl group up to six carbon atoms.
R'" is an amino
group or a substituted amino group.
5
H
The novel compounds of the present invention may be
prepared if desired by reacting the appropriate phosphite
v
or phosphonite such‘as a dialkyl ‘arylphosphonite or a
trialkyl phosphite with theappropriate halo-acid ester or
amide such as an alpha-chloroJbeta-oxo fatty acid ester
The present invention relates to novel insecticidal com
positions containing as the active insecticidal component
vinyl esters of pentavalent phosphorus acids. More spe 10 or amide as shown in the following formula:
ci?cally, the present invention relates to novel and un
'
expectedly superior insecticidal compositions containing
o
0
CH3
0
(X)3P + onaillon'illx —-_» (X)z;O(|J=CHiIJX
vinyl esters of pentavalent phosphorus acid, and a pyre
thrum synergist such as the 2~(2-ethoxyethoxy)ethyl 3,4
15 In this equation X represents the groups de?ned in the
methylenedioxyphenyl acetal of acetaldehyde.
_
The vinyl insecticides particularly contemplated by the
..
generic ‘formula. Speci?c examples of preparations of
present invention may be de?ned by reference to the fol
compounds contemplated for the novel insecticidal com
positions of the present invention are to he found in
US. application Serial No. 704,342, ?led December 23,
1957; Serial No. 704,341, ?led December 23, 1957; Serial
No. 555,753, ?led December 28, 1955; Serial No. 576,786,‘
lowing formula:
?led April 9, 1956; and U.S. 2,802,855, issued August
13, 195 7. Speci?c examples of vinyl esters of pentavalent
wherein each X independently represents R, RO—,
lRHN--, R2N--, RORO—, and
l
phosphorus acids encompassed by Formula 1 are: 2
25
(methoxycarbonyl)-1-methylvinyl dimethyl. phosphate;
dimethyl 1 - methyl - 2 - (5 - phenylpentyloxycarbonyl) -
vinyl phosphate; dimethyl l-methyl-Z-(2-benzyloxyethoxy
\carbonyl)vinyl phosphate; dimethyl l-methyl-Z-(tolyloxy
carbonyl)vinyl phosphate; dimethyl l-methyl-Z- (phenoxy
O
RiiORO
carbonyDvinyl phosphate; 2 - (benzyloxycarbonyl) - 1 ~
R is an alkyl group preferably up to six carbon atoms,
an aryl group such .as phenyl, tolyl, naphthalenyl, anthra
methylvinyl dimethyl phosphate; Z-(p-methoxyphenoxy
carbonyD-l-methylvinyl dimethyl phosphate; diethyl 1
methyl-Z-(p-tolyloxycarbonyl)vinyl phosphate; l-methyl
2-(phenethoxycarbonynvinyl dipropyl phosphate; 2%(p
cenyl or benzyl (preferred), an aralkyl group, the alkyl
portion of which contains up to six carbon atoms and
the aryl portion of which is phenyl, tolyl, naphthalenyl,
anthracenyl or benzyl (preferred). R may be unsubsti
35 methoxybenzyloxycarbonyl) - l - methylvinyl dimethyl
phosphate, dimethyl 2-(alpha-methylbenzyloxycarbonyl)
l-methylvinyl phosphate; dimethyl l-methyl-Z-(Z-phe
tuted or substituted with groups such as amino, nitro and
halogen. Each R" independently represents hydrogen,
noxyethoxycarbonyDvinyl phosphate; 1 - methyl - 2 - (5 -
halogen (preferably chlorine) or an alkyl group of up
phenylpentyloxycarbonyl)vinyldipentyl phosphate; 2-me
to six carbon atoms (preferably methyl). Y is a sulfur 40 thoxycarbonyl-l-methylvinyl methyl p-nitrophenyl phos
atom or an oxygen atom (preferably oxygen).
phate; Z-ethoxycarbonyl-l-methylvinyl ethyl p-nitrophenyl
‘Of the compounds encompassed by this formula, those
falling within the following more speci?c formulae are
phosphate; 2 - (p - chlorophenoxycarbonyl) - 1 - methyl -
preferred:
vinyl dimethyl phosphate; 2 - (p -' chlorobenzyloxycar -
. ~
45
50
bonyl)-1-methylvinyl dimethyl phosphate; 2-(o-chloro
benzyloxycarbonyl)-l-methylvinyl dimethyl phosphate; 2
(2,3-dichlorobenzyloxycarbonyl)-1-methylvinyl dimethyl
phosphate; o—(3,4-dichlorobenzyloxycarbonyl)-1-methyl
vinyl dimethyl phosphate; 2-(p-chloro-alpha-methylben
zyloxycarbonyl)-l-methylvinyl dimethyl phosphate; 2-(5
(p - ?uorophenyl)pentyloxycarbonyl) - 1 - methylvinyl
dimethyl phosphate; 2-(p-iodobeuzyloxyoarbonyl) -l-meth
ylvinyl dimethyl phosphate; 2~(o-bromobenzyloxycar
bonyl)-l-methylvinyl dimethyl phosphate; dimethyl 1
55
methyl - 2 - (2,3,4,5,6 - pentachlorobenzyloxycarbonyl) -
vinyl phosphate; 2d(-p~chlorotolyloxycarbonyl)-l-methyl
vinyl dimethyl phosphate; 2-(-p>-chlorophenoxycarbonyl)
l-methylvinyl dipentyl phosphate; 2-(p-chlorobenzyloxy
In these formulae, R is an alkyl group preferably up
carbonyD-l-methylvinyl diethyl phosphate.
1
to six carbon atoms; an aryl group such as phenyl, tolyl,
naphthaleny’l, anthracenyl or benzyl (preferred), or an 60 Among the compounds encompassed ‘by ‘Formula 2 are:
diethyl l-phenylcarbamoyl-l-propen-2-yl phosphate; di
aralkyl group, the alkyl portion of which contains up to
ethyl l - |(p - nitrophenylcarbamoyl) - 1 - propen - 2 - yl
six carbon atoms and the aryl portion of which is phenyl,
tolyl, naphthalenyl, anthracenyl or benzyl (preferred).
phosphate; diethyl l-(methylphenylcarbamoyl)-1-propen
R may be unsubstituted or substituted with groups such '
2-y1 phosphate.
,
v
3,053,729
4
3
Among the compounds encompassed by Formula 3 are:
methyl l-ethoXycarbonyl-1-propen-2-yl phenylphospho
nate; methyl l-methoxycarbonyl-l-propen-Z-yl phenyl
phosphonate; ethyl 1-ethoxycarbonyl-l-propen-Z-yl phen
ylphosphonate; ethyl Z-methoxycarbonyl-l-methylvinyl
(p-dimethylaminophenyl)phosphonate.
alkyl groups. R may also represent a carboalkoxy group,
i.e., a group containing one or more
(Ii
5
-o-o
alkyl groups. R also encompasses alkyl sulfoxy groups,
Other compounds encompassed by the present invention
i.e., groups containing one or more
are:
2-(2-acetoxyethoxycarbonyl) - 1 - methylvinyl dimethyl
phosphate;
2-(Z-acetoxyethoxycarbonyl)-l-methylvinyl diethyl phos
phate;
alkyl groups.
When R is carboalkyl, carboalkoxy or
alkyl sulfonyl, the alkyl portion is straight chain, branched
2~(2-methoxypropoxycarbonyl)‘-1 - methvinyl dimethyl
chain or cyclic alkyl preferably of l to 20 carbon atoms,
phosphate;
either saturated or unsaturated.
2-(2 - ethoxycarbonylethoxycarbonyl) - 1 - methvinyl di
methyl phosphate;
R.
2-(2-benzoyloxyethoxycarbony1) - 1 - methvinyl dimethyl
phosphate;
R’ is a hydrogen atom or a group of the type de?ned for
R and R’ taken together can represent a divalent
radical, which together with the indicated carbon atoms
bis(2~methoxyethy1) 2-(2-methoxyethoxycarbonyl) - 1
methylvinyl phosphate;
20 forms a cyclic alkyl, carboalkyl, carboalkoxy, or alkyl
sulfoxy group preferably of 1 to 20 carbon atoms, either
Z-ethoxycarbonyl-l-methy1viny1 ethyl 2 - methoxyethyl
saturated or unsaturated. The structures of speci?c syn
phosphate;
ergists encompassed by the present invention follow:
2 - (3 - ethoxycarbonylpropoxycarbonyl) - 1,2 - dimethyl
vinyl dibutyl phosphate;
25 n-Propyl isome:
2-(2 - butoxycarbonylbutoxycarbonyl) - 1 - ethylvinyl di
pentyl phosphate;
O
2-(2-butoxybutoxycarbonyl)-1 - phenylvinyl diisopropyl
phosphate;
bis(2-methoxyethyl) 2-ethoxycarbonyl - 1 - methylvinyl 3O
phosphate;
Z-methoxyethyl Z-methoxycarbonyl-l-methylvinyl methyl
phosphate;
bis(2-acetoxyethyl) Z-ethoxycarbonyl-l-methylvinyl phos
phate;
2-acetoxyethyl 2-ethoxycarbonyl-l-methylvinyl methyl
phosphate;
2-(Z-acetoxyethoxycarbonyl)ethenyl dimethyl phosphate;
Z-(rnethoxycarbonyl)-1-methylvinyl dimethyl thiophos
phate;
o 00 omomorn
\
- n-crncooomomorn
C511
CH2CH.OH:
Piperonyl cyclonene:
O
35
OH—COOC:H5
\
0
CH3
00
J] 1 6H
/
0
c
ilkyl
OH’
13,
40
2-(3 - ethoxycarbonyl-propoxycarbonyl) - 1,2 - dimethyl
vinyl dibutyl dithiophosphate.
It is to be understood, however, that the present inven
H
/
tion is not restricted to the enumerated examples nor to
the generic formulae but encompasses all insecticidal vinyl
esters of pentavalent phosphorus acids.
Pyrethrum synergists are broadly encompassed by the
present invention.
Piperonyl butoxide:
Particularly contemplated are those
50
pyrethrum synergists containing a
0
CHgCHzCH:
CH2
o
CHzO CHaGHzO OHIOHIO (34H?
/ \
0
H20
55
\ 0/
Sulfoxide:
/
group. Of these, it has been found that compounds hav
ing the following structural formula are most etfective:
o
CH7.CH.‘SL.CsH17
Sesoxane:
’ \ i
R,
In this formula, R may represent a straight chain, branched
chain or cyclic alkyl group preferably of 1 to 20 carbon
atoms, either saturated or unsaturated. R may also rep—
resent a carboalkyl group that is a group containing one
or more
65
0
\
CH3
0
The last of the structures shown is the preferred syner
gist of the present invention, namely, 2-(2-eth0xyethoxy)
ethyl 3,4-methylenedioxyphenyl acetal of acetaldehyde.
The synergistic activity of 2-(2-ethoxyethoxy)ethyl 3,
75 4-methylenedioxyphenyl acetal of acetaldehyde is illus
‘
3,053,729
5
trated by the following table giving the results of tests
against the house?y, Musca domestica. The ?rst column
of ?gures shows the number of times the insecticidal ac
tivity of each enumerated compound is increased by the
Compound
addition of 2-i(2-ethoxyethoxy)ethyl 3,4-methylenedioxy
Toxicity
LD-50
index
2 - methoxyearbonyl - 1 - methylvinyl methyl p
nitrophenyl phosphate ________________________ ._
5
phenyl acetal of acetaldehyde. The second column of
?gures shows the toxicity index of each of the compounds
tested without synergist, and the ?gures in column three
show the toxicity index with the presence of *synergist.
100
2 - methoxycarbonyl - 1 - methylvinyl methyl p
nitrophenyl phosphate + 1% 2-(2-ethoxyethoxy)
ethyl 3, 4-methylene-dioxyphenyl aeetal of aeet~
aldehyde
'
'
o. 0061'
'
-
2 - ethoxyearbonyl - 1 - methylvinyl ethyl p - nitro
The extraordinary synergistic properties of the preferred
phenyl phnsnhate
phenyl phosphate + 1% 2~(2-ethoxyethoxy)
0.0011
100
0. 0055
, 1'40
2 - ethoxyearbonyl - 1 - methylvinyl ethyl p - nitro
10
insecticidal compositions of the present invention are im
mediately apparent from the ?gures in column one. Tox
ethyl 3, 4-methylenedioxyphenyl acetal of acet
aldehyde _________________________ __
icity of insecticidally active vinyl esters of pentavalent
2 - methoxycarbonyl - 1 - methylvin
phosphorus acids has been increased as much as thirty
2 - methoxycarbonyl - 1 - methylvinyl ethyl (p
dimethylaminophenyl) phosphonate
0. 068
100
0. 002
3400
dimethylaminophenyl) phosphonate + 1% 2
four times by the addition of 2-(2-ethoxyethoxy)ethyl 3, 15
(2 - ethoxyethoxy) ethyl 3, 4 - methylenedioxy- .
phenyl acetal of acetaldehyde ________________ -_
4-methylenedioxyphenyl acetal of acetaldehyde.
The synergized increase in insecticidal activity effected
by the addition of 2-(2-ethoxyethoxy) ethyl 3,4-methylene~
Increase in toxicity
Toxicity index (Dieldrin as Standard=100)
with 1% 2~(2-ethoxy
ethoxy)ethyl 3,4
methylenedioxyphenyl Without 2-(2-ethoxyWith 1% 2-(2-ethoxy
aeetal of aceteldehyde
ethoxy)ethyl 3,4ethoxy)ethy1 3,4
(number of times)
methylenedioxyphenyl methylenedioxy-phenyl
Compound
acetal of acetaldehyde
2. 45
25. 2
19. 7
Diethyl 2~(dimethylcarbamoyl)-methylvmyl phosphat
Dimethyl 2-(dimethylearbamoyl)-1-methy1vinyl phosph
N,N-diallyl-3-(dimethoxyphoshphinyloxy) erotonamide_.._
N,N-diallyl-2-eh1oro-3-(dimethoxy-phosphinyloxy)crotonarnide _________ __
2-m1ethoxycarbonyl-l-methylvinyl
ethyl p-dimethylaminophenyl phos
n (“19. A
‘ég-ehloroé-(dimethoxyphosphinyloxy)crotopanilide _____________________ __
1]]1
2-(benzyloxyearbonyl)-l-methyl
p
2-(p-chlorobenzyloxycarbonyl)~1-methylviny1 dimethyl phosphate.
2~ethoxycarbonyl-l-methylvinyl ethyl p-nitrophenyl phosphate ________ __
2-methoxycarbonyl-l-methylvinyl methyl p-nitrophenyl phosphate ____ __
2,4-dich1orophenyi ethyl 2‘methoxy-earbonyl-l-methylvinyl phosphate...
120
12
12
30. 4
l1. 8
17. 9
8. 3
34.0
7. 7
4. 2
16
2‘ 0
3. 84
2. 53
1. 4
l. 61
6. 13
acetal of acetaldehyde
295
302
236
'
360
149
143
123
26. 8
71. 5
55. 8
59
59. 5
12. 3
13. 4
18.6
22
42
37
2
The relative toxicity, i.e., toxicity index, given in this
dioxyphenyl acetal of acetaldehyde may also be expressed
table for each compound represents the ratio of the con
centration in weight/volume percent of the standard at
in terms of the LD-SO of a broad spectrum of vinyl esters
of pentavalent phosphorous acids as indicated in the fol
which, under standard test conditions, a 50% mortality
lowing table:
40 of the insects in each test was observed, to the concen
Toxicity of Phosphorus Insecticides With and Without
tration in weight/volume, percent of the toxic agent in‘ the
2 - (2 - Ethoxyethoxy)Ethyl 3,4 - Methylenedioxyphen
solvent at which, under standard test conditions, a 50%
yl Acetal of Acetaldehyde on House?ies
Compound
'
mortality of the insects in each was observed.
'
Toxicity 45
LD-50
- index
~
Relative toxicity (toxicityindex) '
LD-50 of the standard
Dimethyl - 1 - methoxycarbonyi - 1 - propen - 2 - yl
p'hnsnhnte
'
=LD-50 of a test sample>< 100
0, 0054
100
0. 0022
245 50
0, 033
100
Dimethyl - 1 - methoxycarbonyl - 1 - propen- 2 - yl
phosphate + 1% 2-(2-ethoxyethoxy) ethyl 3,
4lm'ethylenedioxyphenyl acetal of aeetaldehyde__
Dimethyl 1 - methyl - 2 - (phenoxycarbonyl) vinyl
phnsnhate
Dirnethyl 1 - methyl - 2 - (phenoxycarbonyl) vinyl
phosphate + 1% 2~(2-ethoxyethoxy) ethyl 3,
4-methylenedioxyphenyl acetal of acetaldehyde-_
>2-(benzyloxycarbonyl)~l-methylviny1
dimethyl
~ phosphate
The quantity of standard employed to give 50% mortality
of the insects in each test was arbitrarily given a numeri
.
0.0165
200
0.0223
100
cal value of 100. The toxicity of a representative prod
55 uct of the invention against house?ies (Musca domestica)
was determined generally following the method described
by Y. P. Sun (Journal of Economic Entomology, .vol.
‘43, page 45 (1950)). Solutions of representative'com
pounds were made up by employing a neutral petroleum
60 distillate lying within the kerosene range as a solvent.
The concentration in weight per volume percent re
quired to give under standard test conditions a 50% ,mor
-2 - (benzyloxyearbonyl) - 1 - methylvinyl dimethyl
phosphate + 1% 2(2-ethoxyethoxy) ethyl 3,
_ 4-methylenedioxyphenyl aeetal of acetaldehyde__
0. 0058 V
2 - (p - chlorobenzyloxycarbonyl) - 1 - methylvinyl
dimethyl phosphate ___________________________ __
384
I
0.023
100
2 - (p - ehlorobenzyloxycarbonyl) - 1 - methylvinyl
dimethyl phosphate + 1% 2-(2-ethoxyethoxy)
ethyl 3, 4-methylenedioxyphenyl acetal of acet
aldehyde
_
0. 0091
253
0. 055
100
- aldehyde ______________________________________ _.
0. 0063
873
. phosphate
0.059
100
0. 003
1267
0. 063
100
0.0025
2520
2 - (2 - aeetoxyethoxycarbonyl) - 1 - methylvinyl
dimethyl phosphate ___________________________ __
.tality to house?ies when employing an insecticidal com
2 - (2 - acetoxyethoxycarbonyl) - 1 - methylvinyl
' dimethyl phosphate + 1% 2-(2-ethoxyethoxy)
, ethyl-3, 4-methylenedioxyphenyl acetal of acet
Dimethyl 2-(dimethylcarbamoyl)-1-methylvinyl
Dimethyl Z-(dimethylcarbamoyi)-1-methylvinyl
phosphate + 1% 2-(2-ethoxyethoxy) ethyl 8,
li-methylenedioxyphenyl acetal of acetaldehyde__
‘Diethyl 2~(dimethylcarbamoyl)-1-n1ethylvinyl
phosphate
Diethyl 2(dimethylcarbamoyl)~1-methylvinyl
position comprising ?ve different synergists all contain
65
.
.
I
O
/
Hgb
70'
' phosphate + 1% 2-(2-ethoxyethoxy) ethyl 3,
. 4~methylenedioxyphenyl acetal of aeetaldehyde__
.ing a
\
0
k, .
4’ - ehloro - 3 - (dimethoxyphosphinyloxy) - eroton
anili e ________________________________________ __
0. 034
100
0. 0044
773
4’ — ehloro - 3 - (dimethoxyphosphinyloxy)-crot0n -
_, anilide + 1% '2- (2-ethoxyethoxy) ethyl 3, 4-
methylenedioxyphenyl acetal of acetaldehyde_-
_
'group combined with three vinyl phosphate insecticides
75 was also ascertained as shown in the following table. '
3,053,729
Increase in toxicity with 1% synergist (expressed in number of times increased over
toxieant without synergist)
Synerglst
.
2-Carbomethoxy-1-methylvinyl ethyl p-dimethyl-
amtinophenyl phospho-
me e
Dimethyl 2~(dimethylcarbamoyl) - 1 - methyl
vinyl phosphate
N,N diallyléi-(dimethoxy
phosphinyloxy)
croton
amide
0
O——CH—~(O CHzCHz)z—O-CH:CH3
C‘Hi
(IJH'
34. o
19.1
30. 4
9. 0
a1
4. 0
6.0
1. 7
7. 7
1. 6
2. 5
0
0
4
0
011,011,011;
2
\
-oH,0 011201110 011101110043.
0
0
{
—CHz-CH-S-CsHi7
C\,
CHEO
O
H-C 0 O (32H;
0
g
C\’ O
\c o
CH:‘i )3]:
4'5
Alkyl
g
0
c\'
CH:
\
on c o
(kg: (11H
0
‘i
Alkyl
CO OCHi-CHq-CH:
/
0
CH,
\
-—-CH—CH-COOOH2—CHa-CH:
—-CH¢ H-CH:
3. 8
O
This table shows the extraordinary ability of the de?ned
synergists to increase the toxicity of vinyl phosphate in
acetaldehyde does not synergize all phosphorus-containing
insecticides as indicated by the following table:
secticides.
The de?ned compounds of the present invention, such
as 2-(2-ethoxyethoxy)ethy1 3,4-methylenedioxyphenyl 55
acetal of acetaldehyde, have in the past been employed as
Compound
synergists for pyrethrum. However, these materials have
Toxicity with 1% 2-(2cthoxy
ethoxy)ethyl 3,4-methylenc
dioxyphenyl acetal 0i acetal
dehyde compared to com
pound alone
never been found effective as synergists for vinyl esters
0,0 - dimethyl - 5 - (1,2 - bis(ethoxycar
of pentavalent phosphorus acid insecticides. It is clear
bonyl)ethy1 dithiophosphate (Mala
that the elfect of these synergists on the pyrethrums 60 thion) _____________________________ .i
0,0-diethyl oap-nitrophenyl thio
differs radically in mechanism from their synergistic
phosphate (Parathion)
effect on the vinyl phosphorus acids of the present com
O-ethyl
ll-pl-nltrophenyl phenyl
phosphorot ioate (EPN) .......... -.
positions because of the radical dilference in the nature
of the insecticides.
1.14
0.63
0. 70
Pyrethrums are mixed esters of
pyrethrolone and cinerolone ketoalcohols with 2-chrysan 65 It is immediately apparent from this table that 2-(2
ethoxyethoxy)ethyl 3,4-methylenedioxyphenyl acetal of
themum carboxylic acids. This material is obtained by
extraction of ground dried chrysanthemum cinerafolium
acetaldehyde does not signi?cantly affect the insect toxic
?owers. The vinyl phosphorus insecticides of the pres
ity of non-vinyl type phosphorus-containing insecticides.
ent compositions, on the other hand, are synthetically
In the case of vinyl esters of pentavalent phosphorus
manufactured and differ radically in their structure and 70 acid insecticides, on the other hand, the addition of this
mode of activity. Though the exact mechanism of the
synergist signi?cantly increases the insecticidal activity of
present synergists on vinyl phosphorus acid esters is not
the phosphorus compound far beyond what might be
clearly understood, it is clear that these synergists are
expected from the additive effectiveness of the compo
quite speci?c in their function. For example, 2-(2
nents in the insecticidal composition.
ethoxyethoxy)ethyl 3,4~methylenedioxyphenyl acetal of 75 The synergists employed in the present invention may
3,053,729
9
thetic insecticides including DDT, benzene hexachloride,
vary considerably in the concentration employed in the
insecticidal mixture. Thus, the synergists of the present
invention may be present in less than 1% and may, if
desired, be employed in concentrations in excess of 10%
by weight of the insecticidal composition. Approximate
ly 1% by weight of the synergist in the insecticidal com
cyanides, tetraethyl pyrophosphate, diethyl p-nitrophenyl
thiophosphate, and the various compounds of arsenic,
lead and/ or ?uorine.
This application is a continuation-in-part of applica
tion Serial No. 777,200, ?led December 1, 1958, now
abandoned.
position is preferred.
I claim as my invention:
The compositions of this invention can be employed
1. An insecticidal composition comprising a phos
for insecticidal purposes by the use of any of the methods
which are conventionally employed in the art. For ex 10 phorus-containing insecticide and a methylenedioxyphenyl
compound, in proportions corresponding to from about
ample, the compounds can either by sprayed or other
0.0001 part to about 2 parts by weight of said insecticide
wise applied in the form of a solution or dispersion or
to from about 1 part to about 10 parts by weight of said
they can be absorbed on an inert, ?nely divided solid
methylenedioxyphenyl compound, said insecticide having
and applied as a dust. Useful solutions for applications
the formula:
by spraying, brushing, dipping and the like can be pre
pared by using as the solvent any of the well-known inert
15
horticultural carriers, including neutral hydrocarbons
such as kerosene and other light mineral oil distillates
of intermediate viscosity and volatility. Adjuvants, such
as spreading or wetting agents, can also be included in 20 wherein R is alkyl of from 1 to 2 carbon atoms, R' is a
the solutions, representative materials of this character
being fatty acid soaps, rosin salts, saponins, gelatin,
casein, long chain fatty alcohols, alkyl aryl sulfonates,
long chain alkyl sulfonates, phenol-ethylene oxide con
densatcs, C12 to C20 amines and ammonium salts, and 25
the like. These solutions can be employed as such, or
more preferably they can be dispersed or emulsi?ed in
water and the resulting aqueous dispersion or emulsion
applied as a spray. Solid carrier materials which can
member of the group consisting of alkyloxy of from 1
to 2 carbon atoms, dimethylaminophenyl, nitrophenyloxy,
Kdichlorophenyloxy and dimethylamino, R" is a member
of the group consisting of hydrogen and chlorine, and
R’” is a member of the group consisting of methoxy,
phenoxy, benzyloxy, chlorobenzyloxy, 2-acetoxyethyl, di
methylamino, diallylamino chlorophenylamino, and ter
tiary-butylamino, and said methylenedioxyphenyl com
pound is a member of the ‘group consisting of sesoxane,
be employed include: talc, bentonite, lime, gypsum, 30 n-propyl isome, piperonyl 'butoxide, piperonyl cyclonene
pyrophyllite and similar inert solid diluents. If desired,
the compounds of the present invention can be employed
as aerosols, as by dispersing the same into the atmos
phere by means of a compressed gas.
and sulfoxide.
2. An insecticidal composition according to claim 1
wherein the methylenedioxyphenyl compound is sesoxane.
3. An insecticidal composition according to claim 2
The concentration of the phosphorus compounds to be 35 wherein the insecticide is dimethyl lamethoxycarbonyl
used in the compositions of the present invention is de
l-propen-Z-yl phosphate.
pendent upon many factors, including the particular
4. An insecticidal composition according to claim 2
compounds utilized, the carrier employed, the method
wherein the insecticide is diethyl 2-(dimethylcarbamoyl)
and conditions of application, and the insect species to
l-methylvinyl phosphate.
5. An insecticidal composition according to claim 2
be controlled, a proper consideration and resolution of 40
these factors being within the skill of those well versed
wherein the insecticide is dimethyl 2-(dimethylcarbam
in the insecticide art. In general, however, the com
oyl) -l-methylvinyl phosphate.
pounds of the present synergized compositions are effec
tive in concentrations of from about 0.01% to 0.5%,
based upon the total weight of the composition, though 45
under the same circumstances as little ‘as about 0.0000=1%
or ‘as much as 2% or even more of the compound can
be employed with good results from an insecticidal
standpoint.
The novel compositions of the present invention may 50
be employed alone or in conjunction with other insecti
cidally active materials. Representative insecticides which
may be added to the present compositions include the
naturally occurring insecticides such as pyrethrum, ro—
tenone, sabadilla, and the like, as well as the various syn 55
References Cited in the ?le of this patent
UNITED STATES PATENTS
2,685,552
Stiles ________ __, ______ __ Aug. 3,1954
2,765,331
2,802,855
2,864,740
2,864,849
2,865,944
Whetstone ____________ _.. Oct. 2,
Whetstone ___________ __ Aug. 13,
Dweley _____________ __ Dec. 16,
Schrader ____________ __ Dec. 16,
Stiles _______________ .._ Dec. 23,
1956
1957
1958
1958
1958
2,891,887
Gilbert _____________ __ June 23, 1959
2,894,014
2,913,367
Stiles ________________ __ July 7, 1959
Dawson ____________ __ Nov. 17, 1959
Документ
Категория
Без категории
Просмотров
0
Размер файла
616 Кб
Теги
1/--страниц
Пожаловаться на содержимое документа