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Патент USA US3097142

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United States Patent 0
3,097,132
rice .
Patented July 9, 1963
2
1
S03 @
3,097,132
FUNGICIDAL PLANT PROTECTION
Christian Wiegand, Wuppertal-Elherfeld, and Ferdinand
Grewe, Cologne-Stammheim, Germany, asiwors to
Farbenfabriken Bayer Aktiengeselischaft, Leverkusen,
Germany, a corporation of Germany
No Drawing. Filed Oct. 4, 1960, Ser. No. 60,289
SOz
Naphthaline-1,5~disulfonate
Claims priority, application Germany Oct. 10, 1959
6 Claims. (Cl. 167-33)
N02
9
The present invention relates to and has as its objects
SO:
new and useful fungicidal plant protecting agents and
methods of combating fungi therewith. The compounds
which were found to be of value to destroy damaging
fungi of plants may be represented by the following gen 15
_ eral formula:
NO2
~
(Di) -nitrophenyl-sulfonate
R:
O
l
9
20
R,
on, X9
in which R1 and R2 stand for lower alkyl radicals, R2
may also be hydrogen, R3 stands for a higher aikyl
radical and R4 stands for possible substituents of the
25
l
Pentachloro~phenate
benzene nucleus, X is a salt-forming ion which renders
the whole molecule water-insoluble or dit?cul-tly soluble
in water.
N
H
It is known that water-soluble salts of l-methyl-2~
phenyl-3-dodecylbenzimidazole can be used as disinfect
2-mercapto—benzhnidazolate
ing agents with fungicidal or bactericidal action. - (See,
>e.g., German Patent 1,040,752.)
35
Furthermore it is known from US. Patent 2,782,204
that certain 1,3-di-higher-alkyl-benzimidazoline-bromides
possess fungicidal properties which make them useful
in the ?eld of disinfection.
It is also known from J.
Pharm. Soc. Japan, vol. 63 (1943), pp. 593-559, that 40
.
@iN\C_S
6
S/
2-mercapto-benzothiazolate
certain 1-higher-alkyl-3-lower~alky1-benzimidazoline salts
and other similar groups which render the above shown
may be used as inert soaps and that some of the com- '
lower alkyl, higher 'alkyl benzimidazoles di?icultly water
pounds mentioned in the aforementioned journal also
soluble or water-insoluble.
'
The groups R1-R4 of‘ the formula of the beginning
tion.
>
45 of this application more speci?cally are:
All these compounds, however, were as yet not used
R1 and R2 lower lalkyls up to 4 carbon atoms, R2 may
for the protection of living plants, because they damage
also be hydrogen, R3 higher alkyls between 8 and 20
possess bactericidal action useful in the ?eld of disinfec
them or because their effect is only of short duration.
In accordance with the present invention it has been
found that insoluble salts of l-lower alkyl-3-higher alkyl
benzimidazoles, even the salts of hydrohalic acids, are
usable for the treatment of living plant cultures. In
cold Water these last mentioned salts are also only dif
?cultly soluble.
Besides the aforementioned hydrohalic acid salts, salts 55
of other acids are naturally also suitable which are dif
?cul-tly soluble or insoluble in cold water.
Most speci?cally compounds of the above said formula
are useful against fungicidal attack in which the ion X
is chloride, bromide, sulfate, nitrate and the like. More 60
complex ions very useful for the above described inven
tion are:
carbon atoms, and R, such groups as lower alkyl, lower
alkoxy, nitro, chlorine, bromine and the like.
The compounds according to the invention are effective
against a series of phytopathogenic fungi, of which
Phytophthora infestans
Alternaria solani
Plasmopara viticola
Venturi inaequalis
‘are principally to be mentioned, without thereby limit
ing the action of these fungi.
EXAMPLES
The fungicidal activity of the compounds to be used
according to the invention are illustrated by way of ex
[F 9 (ON) a]
Hexacyanoferrate
[Cr (CNS) 4.2NH3J9
Reineckate
ample by 1-methyl-3-dodecyl-benzimidazolium salts and
Phytophthora infestans:
Young tomato plants (Bonny Best) are sprayed with
aqueous emulsions formed by mixing the active ingre
dient of the preparations in the stated concentrations.
Auxiliary solvents (equal parts) such as dimethyl for
mamide, chlorobenzene, acetone and the like are useful
.to prepare these emulsions and a non-ionic emulsi?er of
the type arylhydroxypolyglycolether may be used, too,
3,097,132
3
advantageously. 24 hours later, when the plants have
2. A method for protecting
4 plants against fungicidal
dried off, they are placed in a moisture chamber and in
oculated by sprinkling over with zoospores of Phytoph
tlzoraiinfestansr The plants remain until evaluation on
the sixth day 'after inoculation
the moisture chamber
attack: comprising treating the plants with a salt of l
7 lower alkyl-3-higher alkylbenzimidazole of the following
formula:
'
5
' at l8°—20° C. and a relative humidity of 98% to 100%.
01°11“
*
NO:
'
The casualty rate of the treated plants is given in per
cent of the casualty rate of the untreated controls whose
casualty rate is taken as 100. Untreated plants are at
S04
l0 t1
the moment of evaluation completely destroyed by the
fungus.
7'
’ i @N/CH
/b'\
'
Table 1.—-Phytophthora infestans/tomtztoes
3. A method for protecting plants against fungicidal
attack comprising treating the plants with a salt of 1
Casualty rate at prepara
15 lower alkyl-'3-higher alkylbenzimidazole of the following
formula:
tion concentrations in
7 Preparation
percent
0. 025
F‘
*
t
/ \
CH BI“
\ /
If
_
C
CH:
H:
l-
|” 5
15
32
9
H
“0
'
42
3,
"'+"_
N0:
I
'
—SOa
30
(17121325
41 ______________ ._
/
1T‘
_.
NO:
'
\
35
(‘3111125 _+
\
//c-0H3 [FewNn]
N
/
to
3 :
[F8(CN)0]
l3 ______ _.
attack comprising treating the plants with a salt of 1
33
lower alkyl-3-higher alkyl-benzirnidazole having the fol
lowing formula:
1
~
To
l"
(llnHrs
1'3:
J3
+
/N\
R4-
7
N
/
If u
CH;
_
3_
éHg
3_
CH
CH:
\ /
7
5. A method for protecting plants against fungicidal
..
"
,
‘’
N\
|
CH:
\/
3
formula:
\ /
N\
(EH3
4. A method for protecting plants against fungicidal
attack comprising treating the plants with a.’ salt of 1
7
\* OH
_
N
lower alkyl-3-higher alkylbenzimidazole of the following
——
"
[Fe(CN)o]
%
V
V
25
4’
on
a’
r
t
NV
\
$1'2'H25
(1312112: *7 "-l
N
I
0. 0125' 0.00625
45
3_
C-—-CH:
[FMCNM]
6 ______ ..
-
CR1
X9
\e/
1?R1"
36
50 in which R1 stands for a lower alkyl radical having up
to 4 carbon atoms; R2 stands for a member selected from
J3
Untreated control ________ ._' ________________ __
100
the group consisting of hydrogen and lower alkyl radical
having up to 4 carbon atoms; R3 stands for a higher
The compounds useful according to this invention can
alkyl radical having from 8 to 20‘ carbon atoms; R;
be sprayed in a dispersed or emulsi?ed form or also be 5. stands for a member selected from the group consisting
applied in dry form or as dusts. In the case of applica
of hydrogen, lower alkyl, lower alkoxy, chlorine, and
tion as a spraying medium they are ground with suitable
nitro; and X is a salt-forming anion selected from the
wetting and dispersing ‘agents in the presence of inert
*group consisting of chloride, bromide, sulfate, nitrate,
hexacyanoferrate, reineckate, naphthalene-1,5-disulfonate,
materials (such as kaolin, talc or similar substances) or,
nitrophenyl-sulfonate, di-nitrophenyl-sulfonate, penta
together with emulsi?ers, dissolved in suitable solvents.
chlorophenate, Z-mercapto-benzomidazolate and Z-mer
Their continued application with other (even inor
capto-benzothiazolate.
6. A fungicidal composition comprising
ganic) fungicides and/ or insecticides is possible.
We claim:
'
1. A method for protecting plants against fungicidal
attack comprising treating the plants with a salt of 1
lower aIkyI-B-higher':alkylbenzimidazole of the following
formula
(a) A salt of a l-lower alkyl-3-higher alkyl-benzimi
65
dazole'of the following formula:
1'1:
I Qtt l
N
012E257
*
Rt-
P
_
(0
/
I
V
on, X9
$/
L.
1?
R1
in which R17 stands for lower alkyl radicals having
75
up to 4 carbon atoms; R2 stands for a member
'3,097,132
6
selected from the group consisting of hydrogen and
(0) water, and
lower alkyl radicals having up to 4 carbon atoms;
(d) an auxiliary solvent selected from the group con
Ra stands for a higher alkyl radical having from 8
sisting of dimethyl formamide, chlorobenzene and
to 20 carbon atoms; R; stands for a member se-
ace-tone.
lected from the group consisting of hydrogen, lower 5
alkyl, lower alkoxy, chlorine, and nitro; and X is
a salt-forming ion selected from the group consisting of chloride, bromide, sulfate, nitrate, heXacyanoferrate, reineckate, naphthalene~1,5-disulfonate,
References Clted m the ?le of this patent
2,782,204
2,376,233
UNITED STATES PATENTS
Tenenbaum _________ __. Feb. 19, 1957
Herrling et a1_ ________ __ Mal; 3, 1959
535,065
601,091
Belgium _____________ __ Nov. 21, 1958
Canada ______________ __ July 5, 1960
ni-trophenyl-sulfonate, di-nitrophenyl-sulfona-te penta— 10
chlorophenate, Z-mercapto-benzimidazolate, 2-mercapto-benzothiazolate,
(b) a non-ionic emulsi?er,
FOREIGN PATENTS
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