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Патент USA US3092551

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United States Patent Of?ce
3,092,541
Patented June 4, 1963
2
1
The compounds of the general Formula (III) are hy
droxylamides, for example, OzNadialkyl-hydroxylamides,
3,092,541
NEW CARBAMOYLALKYL PHOSPHORUS
ESTER COMPOUNDS
of lower monohalogenated monocarboxylic acids.
_
Ernst Beriger, Allschwil, Switzerland, assignor to Clba
Limited, Basel, Switzerland, :1 company of Switzerland
No Drawing. Filed Feb. 21, 1961, Ser. No. 90,636
Claims priority, application Switzerland Feb. 24, 1960
11 Claims. (Cl. 167-42)
This invention provides organic phosphorus compounds
of the general formula
11-0
0
The reaction components are reacted at the ordinary or
a raised temperature, for example, at a temperature with
in the range of 0° to 120° C., and advantageously 10°
C. to 90“ C. It may be of advantage or convenient to
work in an inert solvent, such as an alcohol or a ketone,
for example, acetone or methanol or to add water and,
10 if desired, to work in an atmosphere of an inert gas, for
example, under nitrogen, and/ or under reduced pressure.
It may also be of advantage to react the aforesaid start
ing materials with the aid of heat in a two-phase system
which consists, for example, of water and an organic
15 solvent, for example, methylene chloride, the relative pro
portions of the aqueous or organic phase varying within
RI
(1)
relatively Wide limits.
As stated above, the compounds of the invention are
valuable agents for combating pests, especially insects
in which R and R, each represent an alkyl, cycloalkyl, 20 and acarids.
aralkyl, aryl or heterocyclic radical which may be sub
Accordingly, the invention also provides pest combat
stituted, and which alkyl radical may be interrupted by at
ing preparations which comprise an active substance of
least'one oxygen atom, R2 represents a hydrogen atom or
the above Formula I in admixture with a liquid or solid
a lower alkyl or lower acyl radical, R3 represents a hydro
diluent.
gen atom or a lower alkyl radical, R4 represents the red: 25
A very wide variety of materials or objects can be pro
cal —CH2—, -~CH2—CHz— or
tected against pests, including harmful insects and acarids,
and a gaseous or liquid or solid substance may be used
as a carrier for the active substance. As such substances
,to be protected or to be used as carriers there may be
30 mentioned, for example, air, especially in rooms, and
6
in which R5 represents a lower alkyl radical, and X repre
sents an oxygen or sulfur atom.
liquids, for example, water in ponds and ?nally any dead
or living solid substratum, for example, objects in living
rooms, cellars, attics or stables, and also pelts, feathers,
The above compounds are new and are valuable agents
wool or the like, and also living organisms of the vege
for combating pests, especially harmful insects and acarids. 35 table or animal kingdom in their very wide variety of
They are active against the various stages of develop
stages of development, provided that they are not sensi
ment, such as eggs, larvae and imagines, and they are both
tive to the pest combating agents.
contact poisons and stomach poisons.
The combating of pests is carried out by the usual meth
The invention also provides a process for the manu
ods, for example, by treating the material or object to be
facture of the compounds of the above Formula I, where 40 protected with the active compound in the form of
in a compound of the formula
vapour, for example, as a fumigant, or in the form of
a dusting or spraying preparation, for example, as a solu
tion or suspension, which may be prepared with water
or an organic solvent, for example, alcohol, petroleum, a
45 tar distillate or the like. The preparations may also be
(II)
in the form of aqueous solutions or aqueous emulsions of
Rr—0
in which R, R, and X have the meanings given above,
organic solvents which contain active substances, and
which emulsions or solutions can be applied to the ob
and Me represents a cation, more especially an alkali
jects or materials to be protected by brushing, spraying
50
metal ion, is reacted with a compound of the formula
or dipping.
The spraying or dusting preparations may contain the
usual inert ?llers or marking agents, for example, kaolin,
0 R:
Hill-Br-C ON
R,
gypsum or bentonite, or other additions such as sul?te
cellulose
waste liquor, cellulose derivatives or the like,
55
(III)
in which R2, R3 and R4 have the meanings given above,
and Hal represents a halogen atom, for example, bromine
or chlorine.
and they may also contain the usual wetting agents or
adherent agents for improving the wetting capacity or
adherent property of the preparations. The pest combat
ing preparations may he made up in powder form, in the
The compounds of the general Formula II are advan 60 form of aqueous dispersions or pastes, or in the form of
self-dispersing oils.
tageously dialkyl esters of dithio phosphoric acid or of
A compound of the Formula I may be the sole active
thiolphosphoric acid, of which the alkyl radical contain
substance present in the preparation or it may be present
1 to 4 carbon atoms, and also alkali metal salts of these
in combination with another insecticide and/ or fungicide.
esters.
3,092,541
4
Such preparations are used for plant protection by the
usual spraying, pouring, dusting or fumigating methods.
The following examples illustrate the invention, the
parts and percentages being by weight unless otherwise
stated, and the relationship of parts by weight to parts by
EXAMPLE 5
22.4 parts of the sodium salt of dimethyldithiophos
phoric acid are stirred with a solution of 12.8 parts of
chloroacetic acid-N~methoxyamide (melting at 41° C.)
in 45 parts by volume of water. The temperature is
maintained for 7 hours at 10 to 15° C., whereupon the
volume being the same as that of the kilogram to the
liter.
EXAMPLE 1
mixture is stirred for another 24 hours at room tempera
ture. The oil is isolated and the aqueous solution is
A solution of 19.8 parts of the sodium‘ salt of dimethyl 10 washed with 50 parts by volume of benzene. The ben
zene solution is combined with the oil, washed with a
dithiophosphoric ‘acid in 40 parts by volume of acetone
small amount of sodium bicarbonate solution and dried
is treated within 5 minutes dropwise with a solution of
over sodium sulfate. The benzene is evaporated in vacuo
13.75 parts of chloroacetic acid-O:N-dimethylhydroxyl
at a bath temperature of 40 to 50‘l C., to yield as residue
amide (melting at 41” C.) in 20 parts by volume of
acetone. The reaction is slightly exothermic. The mix 15 16.4 parts of a crystalline compound of the formula
ture is stirred for one hour at room temperature and then
8
for 2 hours at 40 to 45° C., the precipitated sodium chlo
II
I
ride is ?ltered off and the ?ltrate is evaporated in vacuo
(CHlOhP-SCILCON-O 0H,
at 40° C. The residue is taken up in 50 parts by volume
of methylene chloride and washed with 10 parts by vol 20 melting at 47 to 48° C.
ume of water and then with 2X10 parts by volume of
Analysis-Calculated: P, 12.63%. Found: P, 13.0%.
sodium bicarbonate solution. The solution is dried over
sodium sulfate and evaporated in vacuo, to yield as residue
EXAMPLE 6
20.55 parts of a compound of the formula
As described in Example 5, 23.8 parts of the sodium
25
salt of diethyldithiophosphoric acid are reacted with 11.8
parts of chloroacetic acid-N-methoxyamide, to yield 22.8
parts of a compound of the formula
Analysis.-Calculated: P, 11.95%. Found: P, 11.8%.
EXAMPLE 2
30
As described in Example 1, 22.9 parts of the sodium
salt of diethyldithiophosphoric acid are reacted with 13.75
parts of chloroacetic acid-O:N-dimethylhydroxylamide, to 35
yield 23.5 parts of a compound of the formula
Analysir.—Calculated: P, 11.34%. Found: P, 11.4%.
EXAMPLE 7
As described in Example 5, 19.4 parts of the sodium
salt of dimethyldithiophosphoric acid are reacted with
11.2 parts of chloroacetic acid-N-methylhydroxylarnide
Analysis-Calculated: P, 10.78%. Found: P, 10.6%. 40 (melting at 70 to 71 ° C.), to yield 18.8 parts of a crystal
line compound of the formula
EXAMPLE 3
As described in Example 1, 9.9 parts of the sodium
salt of dimethyldithiophosphoric acid are reacted with 45
8.25 parts of chloroacetic acid-O-methyl-N-isopropylhy
droxylamide (boiling at 55 to 59° C. under a pressure
of 0.08 mm. Hg), to yield 9.7 parts of a compound of
the formula
S
Call-1080)
(CHsO)a1lL|’-SCH5CON—0CH|
Analysis.-Calculated: ‘P, 10.78%. Found: P, 11.2%.
EXAMPLE 4
which on recrystallization from benzene forms white
needles melting at 67° C.
50
AnaIysis.-~Calculated: P, 12.63%. Found: P, 12.7%.
EXAMPLE 8
(a) A solution of 12.35 parts of chloroacetic acid-N
methylhydroxylamide and 22.9 parts of the sodium salt
55 of diethyldithiophosphoric acid in 30 parts by volume of
water is heated to 30° C. The heating is then discon
tinued and the mixture is stirred overnight at room tem
dium salt of diethyldithiophosphoric acid are reacted with
perature. The oil which forms is separated from water.
7.25 parts of chloroacetic acid-O-methyl-N-isopropy1hy
droxylamide, to yield 9.9 parts of a compound of the 60 The water is washed with 50 parts by volume of methyl
ene chloride, the oil is combined with the methylene chlo
formula
ride extract and the whole is agitated with 10 parts by
volume of saturated sodium bicarbonate solution. The
solution is dried over sodium sulfate and evaporated in
(a) As described in Example 1, 10.05 parts of the so
Analysis.-—Calculated: P, 9.82%. Found: P, 9.8%.
(b) As described in Example 1, 10.95 parts of chloro~
acetohydroxamic acid in 25 parts by volume of acetone
are reacted with 19.8 parts of the sodium salt of dimethyl
dithiophosphoric acid by being stirred for 20 hours at
room temperature.
vacuo at 40 to 50” C., to yield as residue 24.8 parts of a
65 compound of the formula
1
7H‘
(ctHlohh-scnrcoN-on
There are obtained 15 parts of a
compound of the formula
Analysis.-Calculated: P, 11.33%. Found: P, 11.28%.
(b) When the salts of the esters of dithiophosphoric
(OH:O)zIIL—SCHICOIIq-—OH
acid are reacted as described above with the hydroxyl
amides shown in the following Table I, the compounds
vinalysis.-—Calculated: P, 13.40%. Found: P, 13.41%. 75 1 to 12 of the Table I are obtained:
1
3,092,541
'
Ogmp.
Esteroldlthllgphosphorlc
0.
an
'
Table I
Hydroxylamlde
i
'
'
02H;
Formulae! ?nal product
5
1 _____ _. (GHaO):P-—S—-Na ..... __ G10Hr-O0—N\
01H;
(OH|0)|1!'—SOHr—O0N\
on
i??ih‘lf?g.
0H
“
(31K;
2..... _. (0,H,o),r-s-Na._--_. ClOHr-CO-—N\
3
C135
(O:H10)|P—S—OHz—O0N\
on
H
01H:
'8'
0111i
(oH.o),P—s—cH,-coN
1.333335%;
OCQHI
S
OCIH|
CsH;
1?
4 _____ .. (C;H5O):1L—S—Na ____ -_ ClOHr-CO-N
01B:
(CgHgOhP-S-CHg-OON
1I§§§£§1?'9B_€§*%_
001115
%
002111
OH|
S
50:“- (CH;O)gP-S—Na ..... -- Br-OHxCHr-GO-N
’
/CH:
(cmmdl-s-cur-c?r-oo-N
00H.
/CH;
3
5_____ _. (CH|O);P-—S—Na ..... .. Br-oH-oo-N
CH: _
/CH.
(omo),P-s-—oH-c0-N\
00m
on,
/0H|
.Is
0H,
/0H,
(cmlo),rL-s-on-oon\
0011,
n
01B:
S!
01111
(0H|0)|1’-—8—OHr—0O—N
OH
3
03H1 (ISO)
77
‘:5
0,117 (150)
1o,mo)nL-s-cm—0o-N\
OH
/CH5
01130 8
OCH|
n .... _.
‘
/CH1 7
—S—K._. cu-om-oo-n
\
_
(CHIJIOHO
'
GHaO
oH.o\s
P calm: 10.787.
Round:
9%?
OCH;
S
/GH|
1L—S—CH:—CO-N
i
g?!“ 936%
\
@<5
12 .... ..
/CH;
P-S _ orb-co __ N
(OH!)ICHO
1
ggglugégggig»
OH
-s-K__ cl-om-oo ___ N
S
gfglugéznl?gf
OH
9 ..... ._ (mmmdL-s-Na .... .. Cl—-OHr—C0—N\
CHgO
gag-331338;?
0e11,
8 ..... .- wmonr-s-m ..... -. C1—-CHr—CO—-N\
CHaO 8
§§§?i3:111?i,%%_
0011.
1 ..... -. (o.H.o>.P-s-Na ____ __ Br—(l3H~C0—N
10 .... ..
§f§?ku1§g?%_
0011,
OH!
H
iigglugl-giggbig?;
OH
3 ..... __ (0H|O]sP—S-—Na ..... .. C1OH:—CO--N
"
Analjsis
OllIld- 83%.
@4»
/CH;
on.o\e
P S-K.-- o1_cH.-co N\
;_
_
(ommno
'
1> s orb-c0 N<
on
‘ rormymnor
EXAMPLE 9
55
(a) A solution of 39.8 parts of the potassium salt of
‘
dimethylthiolphosphoric acid and 727.5 parts of chloro-
__ _
‘
_
v
7
on.
0H
Hound: 113360.
Peale; 11.3397.
_
Analysis.—Calcu1e.ted: P, 10.94%. Found: P, 11.02%.
(c) A Solution of 39-3 W113 of the 1101355111111 5311 of
dim?thY1t_hi°1Ph°$Ph°1'ic acid an‘; 12_-35 P8118 of 6111011»
acetic acid-O:N-dimethylhydroxylamide in 60 parts by
volume of acetone is heated for 8 hours at 40 to 50° C.
who ac1d-N~me§hy1hydr0xy1anude m 30 parts by vol
"me ‘if acetone 18 hqawd _f0r 18 hours at_ 40 to 50“ C.
After working up as described in Example 1, followed 60 Workmg “P as described 111 Example 1 Ylelds 6-3 Pans
by distillation in 7a high vacuum, there are obtained 25.2,
of the compound 0f the formula
parts of the compound of the formula
'
0
Elm
(GHIOJJL-SOHqCONwOH;
E
(‘ml .
(OHIO)! -SCHaOON—OH
boiling at 131 to 135° C. under 0.12 mm. Hg pressure. 65
Analysis.—Calcu1ated: P, 13.52%. Found: P, 13.4%.
Analysis.-—Ca1culated: S, 13.18%. Found: S, 13.0%.
(d) A mixture of 229 parts of the potassium salt of
(b) A Solution of 2239 P8115 0f the Potassium Salt 0f
diethylthiolphosphoric acid and 12.35 parts of chloro
dielhylthiolphosphol'ic acid and .13-7_5 P8118 0f ChlOfO-
acetic acid-N-methylhydroxylamide in 30 parts by volume
awtic acid-0iN-dime’lhylhydl'oxyiamlde in 30 Pam by
of acetone is heated for 18 hours at 40 to 50° C. Working
volume of acetone is heated for 8 hours at 40 to 50" C. 70 up as described in Example 1 yields 17.1 parts of a com
Working up as described in Example 1 yields 14.4 parts of
pound of the formula
the compound of the formula
boiling at 155 to 159° C. under 0.2 mm. Hg pressure.
75
Analysis,--Oa.lculated: P, 12.04%. Found: P, 12.0%.
3,092,541
7
used as a liquid spray concentrate which can be emulsi~
EXAMPLE 10
?ed by being poured into water.
(a) As described in Example 8, 16.55 parts of chloro
(A) To determine the contact effect of this product on
acetic acid-N-methyl-N-acetoxyamide are reacted with
aphids the following experiment was conducted with the
19.8 parts of the sodium salt of dimethyldithiophosphoric
acid in 30 parts of water and 5 parts by volume of acetone 5 use of liquid Sprays containing .mspectively “08% ’ 0'04% '
by being stirred for 16 hours at room temperature. There
o‘%?égriigaglzilggaggz gigggglsf'infested with aphids
are Obtained 24'9 parts of a cmgiound of the ‘formula
were sprayed all over and after 48 hours the eifect achieved
||
|
‘
was determined. When a 100% effect was observed, the
(0HI0)=P—$ 0HaC0N-0C0011:
10 plants were infested with fresh aphids and the effect again
\Ana[ysis___(:a1cu]ated; P, 10_73%, Found; P, 1031173,
checked after another 48 hours. The results so obtained
(b) As described in Example 8, 16.55 parts of chloro-
are summarized in the following Tables II and III.
acetic lacid-N-methyl-N-acetoxyamide are reacted with
F01’ each P1am an Identifying mark was used!
22.08 parts of the sodium salt of diethyldithiophosphoric
+ signi?es that no live aphids were left;
acid in 30 parts of water and 5 parts by volume of ace- 15 - signi?es insu?icient or no effect;
tone by being stirred for 16 hours at room temperature.
/ signi?es good e?ect, only few live aphids left.
Table II
Cone. of
Ex. 8(b)
Ex. 8(b)
Ex. 8(bl
Table I
Table I
Table I
Comp.
Comp.
Comp.
N0. 1
N0. 3
No. 4
active
subst. in
Ex. 1
Ex. 2
131.3
Ex. 4(a)
Ex. 7
Ex. 8(a)
spray liquid,
Ex. 9(a)
Ex. 9(b)
percent
++
+4»
++
++
-|-+
++
++
++
++
++
+4++
++
++
++
++
++
++
4-+
4-4++
++
++
++
4-4++
++
+4-l--l++
++
+4.
++
+
+
+
+
+
/
—
—
+
+
+
+
+
+
+
t
—
—
—
+
+
+
Table III
Effect on aphids 48 hours after relntestatlon
Cone. of
active
principlein
spray liquid,
percent
Ex. 1
131.2
Ex. 3
Ex. 4(a)
Ex. 7
Ex.8(b) Ex.8(b) Ex. Btb)
Table I Table I Table I Ex. 9(a) Ex. 9(b)
Comp.
Comp.
Comp.
Ex. 8(a)
N o. 1
No 3
No 4
1': 1+
J5 4-"
4- +
-
-
+ +
—
—
+ +
/
/
+ +
/
/
+ +
+ +
+ +
+ +
/
/
+
/
+
/
-
—
-
—
—
—
/
I
+
+
—
-
+
+
+
+
I
-
-
-
—
—
—
—
—
—
-
—
-
—
—
—
—..
—
+
+
/
1
— -
l
I
+ +
+ +
+ +
+ +
(B) To determine the effect on aphids by diffusion
There are obtained 29.4 parts of the compound of the 40
through
the leaves the following experiment was con
formula
ducted with the use of liquid sprays containing respec
CH1
tively 0.08%, 0.04%, 0.02% and 0.01% of active prin
(C:Ht0)1i’~SOH=O OIL-0000B:
Analysis.--Calculated: P, 9.82%. Found: P, 9.73%.
EXAMPLE 11
A mixture of 13.75 parts of chloroacetic acid-OzN-di
methylhydroxylamide and 30.8 parts of the potassium salt
of bismethoxy-ethyldithiophosphoric acid are stir-red for
4 hours at the boil in the two-phase system water (120
eiple.
Of the broad beans which were infested with aphids
only on the underside of the leaves, only the upper sur
face of ‘the leaves was sprayed with the liquid sprays
described above and after 48 hours the etfect on the
underside of the leaves was inspected. The results oh
50 tained are summarized in the following Table IV:
Table IV
45
Eiiect on aphids by di?usion
Conoentr. of active principle
in spray liquid, percent
Ex. 1
Ex. 2
Ex. 8(b)
Table I
Ex. 8(b)
Table I
Ex. 9(a)
Ex. 9(b)
Ex. 9(0)
Ex. 9(d)
++++
++++
comp. No 7 comp. N010
' L
parts by volume) :methylene chloride (40 parts by vol
++++
'
‘
To determine the acaricidal effect on the red spider
mite Terranychus urticae liquid sprays of the composition
ume). Working up as described in Example 8 yields 29.0
65 speci?ed in this example were used, each spray contain
parts of a compound of the formula
CH:
(OHtoCIH40)$¥"SCH:GO]1I~OCH;
Analysis-Calculated: P, 8.92%. Found: P, 8.42%.
EXAMPLE l2
2 parts each of the condensation products of Examples
ing 0.04% of the compounds mentioned in the following
Table V.
Test method.--Broad beans strongly infested with red
spinner mites were sprayed all over with the liquid spray
70 concerned and the effect was determined in the following
manner:
Check a: (after 48 hours) to determine the acaricidal
1 to 11 are mixed with 1 part of the condensation prod
effect.
uct from 1 molecular proportion of tertiary octylphenol
Check b: (after another 5 days) to determine the perma
and 8 molecular proportions of ethylene oxide and 7
75
nent acan'cidal effect and/or the \ovicidal e?ect.
parts of isopropanol. The resulting clear solution can be
3,092,541
10
2. An organic phosphorus compound of the formula
R-O
/o
The results are shown in the following Table V:
Table V
Effect on red spider
mite
Compound
Check 5
Check b
Example 3 ...................................... --
+
+
E-
'
+
+
E
‘ 4(1)) -
1EY
4m
__
l
7_
+
+
+
Example 8(a) .................................... -.
l
+
Ex. 80)) Table I, Comp. 1..-..-
.... -_
+
+
---_
+
+
+
+
__
__
Ex. 8(b) Table I, Comp. 2. Ex. 80:) Table 1, Comp. 3.
Ex. 80;) Table I, Comp. 4.
EX. 8(b) Table I, Comp. 5Ex. 80)) Table I, Comp 8-
Ex. 801; Table I, Comp. 9 . . . _ . _
. . _ _ ._
Ex. 80) Table 1, Comp. l1--.
.
Ex. 80)) Table 1, Comp. 12
Example 11 _____________ _-
+
I
+
+
I
+
+
-|
+
I
I
/
I
\P-s-Lomlo/ olcnnyLH
L
Jp-l
5
Rr-O
in which R and R1 each represents an alkyl radical con
taining at most 4 carbon atoms, m, n and p each rep
10 resents a whole number of at the most 2, and x and y
each represents a whole number of at the most 4.
3. An organic phosphorus compound of the formula
15
+
in which R, R1 ‘and R2 each represents an alkyl radical
No'rn.—~ + signi?es: All red spider mites destroyed, / sig 20 containing at most 4 carbon atoms and m and p each
represents a whole number of at the most 2, and x and
nines: Good acaricidal e?fect; only few spider mites left
a we.
y each represents a whole number of at the most 4.
The compounds of Examples 1 to 11 further have a good
to very good stomach poison e?ect on Musca domestica, 25
Carausius morosus, Orgyia gonostigma and Gastroidea
viridula.
4. An organic phosphorus compound of the formula
'
To manufacture liquid spray concentrates there may
‘also be used wetting and emulsifying agents other than
vthose mentioned above. There may be used non-ionic 30
in which R, R1 and R2 each represents an alkyl radical
products, for example condensation products of aliphatic
containing at most 4 carbon atoms and m and ,0 each
represents a whole number of at the most 2, and x and
y each represents a whole number of at the most 4.
alcohols, amines or carboxylic acids containing a long
chain hydrocarbon radical of about 10 to 30 carbon atoms
with ethylene oxide, such as the condensation product
from: Octadecyl alcohol with 25 to '30 mols of ethylene
oxide, or soybean fatty acid with 30 mols of ethylene
oxide, or commercial olcylamine with 15 mols of ethylene
oxide, or dodecylmeroaptan with 12 mols of ethylene
oxide.
5. An organic phosphorus compound of the formula
'
As suitable anionic emulsi?ers there may be mentioned: 40
the sodium salt of dodecyl alcohol sulfuric acid ester,
the sodium salt of dodecylbenzenesultonic acid, the po
in which R, R1 and R2 each represents an alkyl radical
tassium or tricthanolarnine salt of oleic or abietic acid
or of mixtures of these acids, and the sodium salt of a
containing at most 4 carbon atoms and m and it each rep
resents a whole number of at the most 2 and x and y
each represents a whole number of at the most 4.
petroleum-sulfonic acid.
Instead of with isopropanol the liquid spray concen
trates may be prepared with other solvents, for example
45
6. An organic phosphorus compound of the formula
11-0
ethanol, methanol, butanol, acetone, methylethyl ketone,
methylcyclohexanol, benzene, toluene, xylene, kerosenes,
B-r-O
/
>€-s—<oH|>-- ( /
0
m
N
\ F
or petroleum fractions. Likewise suitable are mixtures of
di?erent solvents.
EXAMPLE l3
in which R, R1 and R3 each represents an alkyl radical
containing at most 4 carbon atoms and m and n each rep
2 parts each of the condensation products of Examples
resents a whole number of at the most 2 and x and y each
1 to 11 are mixed with 9 parts of chalk and 1 part of 55 represents a whole number of at the most 4.
wetting agent. A dusting powder is obtained from which
liquid sprays can be prepared by suspension in water.
7. An organic phosphorus compound of the formula
When the walls of stables \are treated with such a spray
containing 0.04% of active principle, good effects against
?ies and midges are obtained.
What is claimed is:
60
1. An organic phosphorus compound of the formula
in which R represents an alkyl radical containing at most
65 4 carbon atoms, R1 represents a cyclohexyl radical, and
m, n and p each represents a whole number of at the
most 2 and x and y each represents a whole number of
at the most 4.
8. An organic phosphorus compound of the formula
70
in which R and R, each represents an alkyl radical con
taining at most 4 carbon atoms, m, n and p each rep
resents a whole number of at the most 2, and x and y
each represents a whole number of at the most 4.
75
3,092,541
11
12
in which R represents an alkyl radical containing at most
4 carbon atoms, R1 represents a cyclohexyl radical, and
4 carbon atoms, R3 represents a member selected from
the group consisting of a hydrogen atom and an alkyl
radical containing at most 4 carbon atoms, R4 represents
a member selected from the ‘group consisting of the group
-—CH2--, the group -—CH2—CH2— and the group
m, n and p each represents a Whole number of at the
most 2 and x and y each represents a whole number of
at the most 4.
9. The compound of the formula
S
OH:
(CHiO):iL—SCH;OOIlI—O 0H.
10. The compound of the formula
CH;
(CII;O)zl>-S—CH;~CO—I1I—0H
10 in which R, represents an alkyl radical containing at
most 4 carbon atoms, and X represents a member selected
from the group consisting of an oxygen atom and a sulfur
‘atom.
11. The compound of the formula
16. A preparation for combating pests which com
CH,
(CaHsO):ii’-—S—CH:=CO—N—O—CH;
15 prises an organic phosphorus compound of the formula
0
12. The compound of the formula
s
0H,
(C:Hr0):lIl’——S-—-(|JH—C0—N/
0 R1
CH3
20
R:
00H,
13. The compound of the formula
in which R, R1 to R5 and X have the meanings given in
0
CH:
(0Ht0):i>—s-0H,—co—N
OCH;
claim 15, in admixture with a member selected from the
25 group consisting of a pesticidally inactive carrier, a dis
persing agent, a wetting agent, a herbicide and another
pesticide.
14. The compound of the formula
0
17. The method of controlling pests on materials that
are subject to attack by pests, which comprises applying
CH|
30 to said materials a pesticidal amount of an organic phos
(C1H|O):iL—-S-CHr—CO—-N/
phorus compound of the formula
00H,
15. An organic phosphorus compound of the formula
R-o
¢o
P-—S-—R4-—O
35
OR;
in which R, R1 to R5 and X have the meanings given in
in which R and R1 each represents a member selected 40 claim 15.
from the ‘group consisting of an alkyl radical containing
at most 18 carbon atoms, a lower alkoxy lower alkyl
References Cited in the ?le of this patent
radical and a cyclohexyl radical, R, represents a member
selected from the group consisting of a hydrogen atom,
UNITED STATES PATENTS
an alkyl radical containing at most 4 carbon atoms and 45
a radical of the formula
Rel
wherein R5 represents an alkyl radical containing at most
2,959,608
Crouch et a1 ___________ __ Nov. 8, 1960
FOREIGN PATENTS
663,270
791,824
Great Britain ________ __ Dec. 19, 1951
Great Britain ________ .._ Mar. 12, 1958
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