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Патент USA US3098011

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States Patent 0
1
3,098,001
Patented July 16, 1963
2
substituents [are as set forth in Table 1 below have been
3,098,001
Horst Werres, Rerlin-Charlottenburg, Alfred Czyzewski,
found to be particularly effective aearicidal agents:
ACARICIDE AGENT
Berlin-Tempelhof, and Albert Jager, Berlin-Hermsdorf,
Germany, assignors to Schering A.G., Berlin, Germany
No Drawing. Filed Dec. 28, 1960, Ser. No. 102,080
Claims priority, application Germany Dec. 28, 1959
10 (Ilaims. (Cl. 167-30)
TABLE 1
Compound N0.
X1
Qom
The present invention relates to a new aoaricide agent,
and more particularly to agents for com-batting plant
damaging spider mites.
Various chemicals have been suggested for combat-ting
plant damaging mites, for example the ‘fred spider.”
However, in most cases the agent used is only effective 15
against ‘certain development stages of the spider mites so
2.4
Rs
Benzyl.
p-Chlorobenzyl.
Benzyl.
p-Ohlorobenzyl.
B enzyl .
p‘Chlorobenzyl.
Benzyl.
p-Chlorobenzyl.
It should, however, be noted that compounds which are
that a complete destruction has not been obtainable prior
substituted at the nitrogen atom with other alkyl groups
to the present invention.
or wherein the benzyl radical is substituted by other
It is particularly true that the initial action of the
halogen-s are also active acaricidal agents.
known acaricides is too low, or the same are only effec 20
The acaricidal agents of the present invention have
tive as ovicides. In addition, it has been particularly
been found to be much more e?fective than O-phenyl
di?icult to develop acaricides which are both effective and
esters or S-phenyl esters of carbamic acids or mono
which are compatible with plants.
thiocarbamic acid-s.
It is accordingly a primary object of the present in
The compounds of the present invention may be used
vention to provide an acaricidal agent which avoids all 25 in various acaricidal dosages in application thereof to an
of the above mentioned disadvantages of the known
area subject to spider mites attack in order to combat
agents.
such spider mites attack, and the range of dosage may
It is another object of the present invention to provide
vary quite considerably in view of the fact that very low
a new acaricide agent which is highly effective against
30 dosages are e?iective, and very high dosages are com
all development stages of spider mites, and which in ad
patible with continuation of the plant life.
The agents can be applied with any carrier commonly
dition is compatible with plants.
It is yet another object of the present invention to pro
vide a plant-compatible acaricidal agent which is highly
used for agents of this type, and in any form, for ex
ample in the form of ‘a suspension, emulsion, powder,
effective against all development stages of plant damag
35 solution, aerosol, or the like. The agents may be ap
ing parasites such as the spider mites, etc.
plied alone ‘or in admixture with other insecticides, fungi
Other objects and advantages of the present invention
cides, or the like.
will be apparent from a further reading of the ‘speci?ca
Among the suitable liquid and solid carriers for the
tion and of the appended claims.
‘
compounds of the present invention are water, mineral
With the above and other objects in view, the present
oils, organic solvents, emulsifying or suspending agents,
invention mainly comprises an acaricide composition com 40 bentonite, fuller’s earth, gypsum, lime, diatomaceous
prising a ‘carrier and a compound of the formula:
earth, pyrophyllite, silica, talc, chalk, or the like. Emulsi
?ers, wetting ‘agents or binding ‘agents may be added to
the preparations as well as carrier gases, odoriferous
45 substances, substances for attracting, or repellants. As
indicated the preparations can be in the ‘form of dust,
wherein R1 is selected ‘from the group consisting of hy
agents for spreading, gnanulates, for spraying, atomizable
drogen and 1alkyl, wherein R2 is alkyl, wherein X1 is
liquids, aerosols, etc.
selected from the group consisting of oxygen and sulfur,
The following examples are illustrative of prepara
wherein X2 is selected from the group consisting of oxy 50 tions prepared in accordance with the present invention.
gen and sulfur, and wherein R3 is selected from the group
consisting of benzyl and halogen-substituted benzyl radi
cal-s.
The substituent R1 as indicated above is either hydro
gen or an alkyl, and when it is an alkyl it is preferably a 55
lower alkyl and most preferably methyl. Likewise, R2
which is an alkyl is preferably a lower alkyl and most
preferably methyl.
As indicated, the substituent R3 is either benzyl or a
halogen-substituted benzyl.
The scope of the invention is not, however, meant to be
limited to the speci?c details of the examples:
Example 1
PREPARATION OF A WWTTABLE POWDER FOR
'SPRAYING
A mixture is prepared of:
50% N,N-dimethylthiocarbamic acid benzyl ester
Preferably when R3 is a 60 10% lignin sulfonic acid (calcium salt)
5% sodium salt of sulfonated ethylmethyloleylamide
halogen-substituted benzyl it is a benzyl substituted by
one or more halogens, most preferably by chlorine and/ or
3 % urea-formaldehyde condensate
2% starch decomposition product
30% carrier (aluminum silicate)
ent invention are partially known compounds which can 65
Example 2
be produced by known methods, for example by the
PREPARATION OF AN EhIULSION CONCENTRATE
reaction of the corresponding substituted benzyl halo
A preparation is prepared ‘of:
genide with the salt (preferably the alkali metal or am
20% N,N-dimethylthiocarbamic acid benzyl ester
monium salt) of the corresponding carbamic acid, for
bromine.
The compounds which are used according to the pres
example the monothiocarbamic acid or the dithiocar 70 1% of a mixture of ‘oil soluble sulfonates and polyoxy
ethylene products
biamic acid.
Compounds of the above general formula wherein the
89% solvent naphtha
3,098,001
4
sulfur, and wherein R3 is selected from the group con
The activity of the new acaricidal agents of the present
invention is apparent from Table 2 below:
sisting of benzyl and halogen-substituted benzyl radicals.
3. The method of combatting spider mites attack,
TABLE 2
Preparation
of compound
Percent
active
of Table 1
Substance
which comprises applying to an area subject to spider‘
mites attack a compound of the formula:
Percent action after number of days
dicated
1
3
A+N L
A+N L
A+N L
100
100
100
98
100
80
90
80
100
100
100
100
100
90
100
90
100
100
100
100
100
100
100
100
CH3
/
7
N- C-S-R;
CH3
100
100
100
95
100
70
90
70
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
E
100
100
100
100
100
100
100
100
10
0
wherein R3 is benzyl.
4. The method of combatting spider mites attack,
which comprises applying to an area subject to spider
mites attack a compound of the formula:
15
wherein R3 is p-chlorobenzyl.
The tests Were carried out in such manner that bush
5. The method of combatting spider mites attack,
beans which were infested with bean spider mites of all 20 which comprises applying to an area subject to spider
stages of developments (adults~—A), (nymphs—N),
mites attack a compound of the formula:
(larvae—L) and (summer eggs-E) were treated with
aqueous suspensions of the agents indicated. The acari
CH3
cidal effect was determined after 1, 3 and 7 days.
The above ?gures are the result of 15 parallel series 25
of experiments under equal conditions.
The amount of the active substance of the compounds
wherein R3 is benzyl.
6. The method of combatting spider mites attack,
of this invention which are used in the preparations for
which comprises applying to an area subject to spider
combatting spider mites may vary in ample limits. It
depends on the kind of formulation, the kind of appli 30 mites attack a compound of the formula:
cation, the desired measure of control and the kind of
the pests to be combatted. Depending on the kind of
preparation the amount of active substance in the agent
may be about 0.1 to 90 percent by weight. The agents
may be applied in concentrations as low as 0.01 percent 35 wherein R3 is p-chlorobenzyl.
by weight. Usually good results are received by concen
7. The method of combatting spider mites attack,
trations between about 0.025 and 10 percent ‘in liquid or
which comprises applying to an area subject to spider
solid carriers. For special purposes higher concentrations
mites attack a compolgid of the formula:
may be desired for instance as high as about 20 percent.
Without further analysis, the foregoing will so fully 40
reveal the gist of the present invention that others can by
_
applying current knowledge readily adapt it for various
applications without omitting features that, from the stand
point of prior ‘art, fairly constitute essential characterisics
C?z (H)
wherein R3 is benzyl.
8. The method ‘of combatting spider mites attack,
which comprises applying to an area subject to spider
of the generic or speci?c aspects of this invention and, 45 mites attack a compound of the formula:
H
therefore, such adaptations should and are intended to be
comprehended within the meaning and range of equiva
lence of the following claims.
What is claimed as new and desired to be secured by
Letters Patent is:
1. The method of killing acarids, which comprises con
tacting the acarids with a compound of the formula:
wherein R1 is selected from the group consisting of hydro
gen and alkyl, wherein R2 is alkyl, wherein X1 is selected
>N—C—S——R;
CH3
0
50 wherein R3 is p-chlorobenzyl.
9. The method of combatting spider mites attack,
which comprises applying to an area subject to spider
mites attack a compound of the formula:
10. The method of combatting spider mites attack,
which comprises applying to an area subject to spider
from the group consisting of oxygen and sulfur, wherein
mites
attack a compound of the formula:
60
X2 is selected from the group consisting of oxygen and
CH3
sulfur, and wherein R3 is selected from the group con
N—C~O—Ra
sisting of benzyl and halogen-substituted benzyl radicals.
/
2. The method of combatting spider mites attack, which
CH3
0
wherein R3 is p-chlorobenzyl.
comprises applying to an area subject to spider mites
65
attack a compound of the formula:
References Cited in the ?le of this patent
UNITED STATES PATENTS
wherein R1 is selected from the group consisting of hydro~
gen and alkyl, wherein R2 is alkyl, wherein X1 is selected
from the group consisting of oxygen and sulfur, wherein
X2 is selected from the group consisting of oxygen and
2,854,374
2,990,319
Huisman ____________ __ Sept. 30, 1958
Jones _______________ __ June 27, 1961
320,209
Switzerland __________ __ May 15, 1957
692,659
Germany ____________ _._. May 30, 1940.
FOREIGN PATENTS
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