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Патент USA US3058889

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3,058,879
vin
Patented 0ct._'16,v'1'962~
2
The production thus is “carried out by reacting the corre
sponding diphenyl ester monochlorides of phosphoric acid
'
3,058,879 '
or thiophosphoric acid with ammonia or the correspond
ing amines in an aqueous or inert medium, or also by
ACARICIDAL AND OVICIDAL AGENTS
Hugo Malz and Richard Wegler, Leverkusen, and Giinter
Untersteuhtifer, ()pladen, Germany, assignors to Far
esteri?cation of the corresponding amido- or arnidothio
benfabriken Bayer Aktiengesellschaft, Leverkusen,
phosphoric acid dichlorides-with the corresponding phe
Germany, a corporation of Germany
nols or alkali metal phenolates.
No Drawing. Filed Sept. 16, 1959, Ser. No. 840,253
Claims priority, application Germany Oct. 3, 1958
6 Claims. (Cl. 167-33)
The present invention relates to and has ‘as its objects
new and useful pesticidal agents with acaricidal and
ovicidal action containing as active ingredients com
pounds of the following general formula
R1
invention are barely water-soluble and can therefore be
separated in a simple manner from the aqueous mother
liquors.
-
sidered talc, chalk, bentonite, k-ieselguhr and the like.
N-P(o R3):
.
in which R, and R2 stand for hydrogen, alkyl or alkenyl
radicals, R1 and?Rz together with the nitrogen atom may
When emu-lsi?able dusts are to be prepared, it is advisable
to use suitable emulsi?ers, particularly those having a
non-ionogenic basis such as aryl-hydroxy-polyglycol
ethers of which various types are on the market.
also form a 5- or 6~member ring system, which also may
For the preparation of liquid combinations it is possible
be interrupted by further hetero atoms; R, ‘furthermore
may be a lower alkylene radical bearing another
to‘ employ solutions of the phosphoric acid or thiophos
phoric acid esters to be used according to the invention
not only in suitable inert organic solvents, but also in
water in combination with suitable emulsi?ers and aux
iliary solvents. Organic ‘solvents are for'example alco
0(s)
' —III—P (OR3)z—group
Ra
'
The plant protective agents claimed are applied in usual
manner in the ‘form of solutions or dusts. As solid ex
tenders or diluents for dusts there are chie?y to be con
0 (S)
R2
In this case it is ex
pedient ‘to add the acid chlorides dropwise to aqueous
solutions of the phenolates or to ‘aqueous-alkaline solu
10 tions of the phenols. All compounds according to the
hols, hydrocarbons, chie?y chlorinated low molecular
-
weight hydrocarbons such as chloroform, trichloro~eth
ylene and the like. For the preparation of aqueous dilu
R3 at last stands for a halo-substituted phenyl radical.
This invention further relates to the protection of plant
against attack by the above mentioned pests.
tions it is advantageous to start from a mixture of active
In accordance with the present invention it has been
found that these compounds show an exceedingly strong
substance, emulsi?er, auxiliary solvent, the auxiliary sol
vents chie?y to be considered being dimethylformamide,
acaricidal and especially ovicidal activity. Since this
acetone, xylene or o-dichlorobenzene and the emulsi?ers
used being those described above.
The agents are aplied in the manner customary for
other phosphoric acid esters.
The following examples are given for the purpose of
~ _ activity also exists against pests which have become
resistant to plant protective agents based on present com
merical phosphoric acid esters, these agents may e?ec
tively be used for combating, for example, spider mites
in which such resistance phenomena have chie?y been
observed.
As acaricidal or ovicidal plant protective agents in the
illustrating the invention.
Example 1
40'
sense of the present invention there are chie?y to be
,Test on spider mites (Tetranychus telarius) which are
considered the above amidophosphoric ‘acid or amidothio
highly resistant to organic phosphoric acid esters.
phosphoric acid esters of the following formula
Bean plants which were strongly infested with spider
mites-of
all stages of development were sprayed with
45
R1
0(5)
aqueous emulsions at various concentrations of the fol
,N—P (0 R3).
_
lowing active substance.
1.:
More particularly in this formula R1 and R2 denote sim
ilar or di?erent radicals such as hydrogen or a saturated 50
or unsaturated alkyl radical which eventually may be
substituted. R1 and R2 may also form a heterocyclic ring
together with the nitrogen atom, for example an ethylene
amounts by weight of acetone and a commercial benzyl
hydroxy-diphenyl polyglycol ether-emulsi?er type.
idine ring. Finally, K; may also denote an alkylene such 55
as a methylene, ethylene or propylene radical serving for
,_ the linkage of two molecule radicals of the above ‘for
mula via nitrogen _atoms._ The alkylene chain also may
be i?terruptedby heteroatoms such as nitrogen, oxygen,
,
“
.
Thecompounds according to the invention are crys
talline products or oily, in some cases distilla-ble liquids.
Some are known from the literature, eg from US.
Percent active
substance
Percent mor
tality of mov-
Degree of
(pure active
able stages
infestation
subst. in
after 48
after 8
aqueous
hours
days
80
20
10
0
0
2
emulsion)
sulfur and the like. As substituents for R1 or R2 there
may be considered inter alia halogens, amino groups,
other or thioether radicals and the like. R3 in the above
formula denotes a‘ halophenyl radical which may further
more be substituted by nitro or amino groups, but also
and the like.
O
The emulsions were prepared with the use of same
imine, morpholine, thiamorpholine, piperazine or piper
by alkyl, alkoxy, alkylmercapto, sulfoxide, sul'fone groups
(Giana-halogen,
0.05
0. 025
0.0125
65
Mortality of movable stages after 48 hours means that
all pests which still showed some movement were counted
as living pests.
The damage of infestation has been counted by the
damaging numbers.
Patents 2,615,038and 2,615,037. If they are novel they 70
0=no damage
maybe prepared exactly by the same methodsas they
1=very slight infestation
are known for’the preparation of the known substances.
"
7
v
'
3,058,879
2=slight infestation
3=medium infestation
4=heavy infestation
5 =very heavy infestation.
0
Example 2
vOvicidal action against eggs of highly resistant spider
mites (Tetfanychus telarius):
0(8)
7
Eggs on Phaseolus vulgaris (string beans) which were
24 hours old were sprayed with aqueous emulsions of the 10
above mentioned active substance and the mortality was
determined after 8 days.
0(s)
7
' '
Percent active
' Percent;
active subst.
in aqueous
after 8
days
substance (pure
0(S)
15
killed
emulsion)
07(3)
0.05
0. 02,5
97
50
We claim:
20
'
.
'
,
1. A method of combating mites and eggs thereof on
a plant which comprises treating the plant'with an active
amount of a compound of the following’ formula
The emulsions have been prepared’ as described in Ex
ample 1.,
0(5)
r
V E'Jéample 3
25
7 Permanent ovicidal action against eggs of highly re-'
sistant spider mites (Tetranychus telarius): ]
V
it
0
V
V
V
2. A method 'of combating mitestand eggs thereof-on
a plant which comprises treating the plant with an actlve
amount of a compound of ‘the Vfollowing formula
a In order to determine the permanent etfect of the above
mentioned compound, sprayed bean plants were infested
after 24 hours, 3 days and 9 days with females laying
eggs on the sprayed plants. The table shows the per
centage of eggs killed'which had been laid'during the}
aforesaid periods.
7
Percent
active
7
" 3, A method of combating mites and eggs thereof _on
Percent eggs killed which hag,
been laidaiter;
35 a plant which comprises treating the plant with an active
amount of a compound of the followingrformular
‘
substance
24 hours _ 3 days
0. 05
V
O. 025
97"
50
V
t,
r
94
38
N—P(O Rs)?
9 days
'40
V
"
'
7
V
R27
,_
.
t
V
,
in which R1 stands for a member selected’ from. the group
41.5,
732.5
consisting of hydrogen,’ a lower alkyl, a lower alkenyl
and
;
'
a
a
The emulsions have been prepared as described: in’ Ex- “45 '
amplel.
7'
V
-
11?-
,
lower allzylene-IYI-P (0 R3):
Similarly good combating results can be achieved with
7 theme of other representatives of the claimed class of
'
'
R57
‘
_
,
R2 stands for a member selected from the; group con
compounds; In the following table some of thesecom
sisting of hydrogen, lower alkyl and lower alkenyl; and
pounds are listed by way of example, without however
limiting the claimed classrof compounds in any way'byv 50 when R1 and R2 areataken together with the nitrogen
this compilation.
atom, they form a, member selected from the group con
sisting oftethyleneimino, morpholino, ,thia’morpholino,
V
, 'Epiperazino 'and p
'perjidino radicals; and R3 ‘stands for a
halo-substituted phenyl radical.
9(3) 7
7
,
r
»
V
a
p
4; An acaricidal androvicidal agent’ containing,
(a) an active substance of'the, grouplof;;an1idophos-'
' phoric acid 'diaryl esters of the followingkformula
r
in which R1 stands for ameinberrselecterddfrom the
' ‘ group consisting of hydrogen,- a'lowe'rrallqfl,v a lower
alkenyl and
T
'1
r
'
.
V
‘
'5 lower elkylene-lr‘r-gw Ra)’:
or
J'l
'
t
7c
"
' R2 stands for a member selected, from thepgroup con
~- sisting of hydrogen, lower alkyl andrrlower ,alkenyl;
and 'whenRL and R2 are takengtogether with the
O
V
nitrogen atom',¢they form a member selected from
a; the group consisting ofjethyleneiminmimorpholino,
0(8)
thiamorpholino, piperazino and piperidino radicals;
is}- and’
R3 vstands for a ‘halo-‘substituted phenyl radical;
3,058,879
References Cited in the ?le of this patent
UNITED STATES PATENTS
(b) a commercially non-ionic emulsi?er;
(c) an auxiliary solvent;
(d) water.
5. An acaricidal and ovicidal agent containing
(a) an active substance of the following formula
2,615,037
2,615,038
2,615,039
2,635,112
2,759,937
2,802,823
(b) a commercially non-ionic emulsi?er;
(c) an auxiliary solvent;
(d) water.
6. An acaricidal and ovicidal agent containing
(a) ‘an active substance of the ‘following formula
2,862,017
1°
2,994,638
Moyle _______________ .._ Oct. 21,
Moyle _______________ __ Oct. 21,
Drake _______________ __ Oct. 21,
Fields _______________ ___ Apr. 14,
Du Breuil ____________ __ Aug. 21,
1952
1952
‘1952
1953
1956
Tolkmith et al ________ __ Aug. 13, 1957
Schrader et a1 _________ .__ Nov. 25, 1958
Malz et al ____________ __ Aug. '1, 1961
OTHER REFERENCES
Sexton: “The Organic Chemist’s Approach to Chemo
therapy,” pages 1-13 of “Selective Toxicity and Anti
“ biotics,” Society of Experimental Biology (S.E.B.) Symp.
No.1II, vol. III, 1949.
(b) a commercially non-ionic emulsi?er;
(c) an auxiliary solvent;
(d) water.
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