Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
3L~3~3~
The present invention relates to herbicidal agents
containing substltuted acetanilides as herbicidal active ingre-
dients an~ N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine as an-
tagonistic agent, and a process for the selective control of un-
wanted plant growth with these herbicidal agents~
The present invention is concerned with a herbicidal
agent a herbicidal agent containing at least one subsituted aceta-
nilide of the formula
~ ~ 2
~ r\ I,
CO-CH2-X
Rl ,
where R denotes hydrogen, linear or branched alkyl or alkoxy of
up to 5 carbon atoms, Rl denotes hydrogen, halogen, or linear or
branched alkyl of alkoxy of up to 5 carbon atoms, R2 denotes
hydrogen, halogen, or linear or branched alkyl or alkoxy of up to
5 carbon atoms, R together with R2 denotes an alkylPne chain of
up to 6 carbon atoms which is linked in the o~position and may be
substituted by linear or branched alkyl of up to 4 carbon atoms,
X denotes chlorine or bromine, and A denotes an azole ring con-
taining 1 to 4 nitrogen atoms which is attached via a ring nitro-
gen atom and may be mono- or polysubstituted by halogen, phenyl,
alkyl~ alkoxy, alkylthio or perfluoroalkyl, each of up to 4 carbon
atoms, cyano, carboxy, carbalkoxy of up to 4 carbon atoms ln the
alkoxy, or alkanoyl o up to 4 carbon atoms, or A denotes a salt
of an azole riny containing 2 or 3 nitrogen atoms, as herbicidal
active ingredient, and N-dichloroacetyl-2,2-dlmethyl-1,3-oxazoli-
dine as antagonistic agent, the ratio of acetanilide to N-dichlo-
roacetyl-2,2-dimethyl-1,3-oxazolidine being from 1:2 to 1:0.01
parts by weight.
Substltuted acetanilides of the formula
-- 1 --
,-, ~
....
.~
~ ~ 3~.03~
~ ~ o-CH -X I,
where R denotes hydrogen, linear or branched alkyl or alkoxy~of
up to 5 c~xbon atoms, R denotes hydrogen, halogen, or linear or
branched alkyl or alkoxy of up to 5 carbon atoms, R2 denotes hy-
drogen, halogen, or llnear or branched alkyl or alkoxy of up to
5 carbon atoms, R together with R2 denotes an alkylene chain
of up to 6 carbon atoms whlch is linked in the o-position and
may be substituted by linear or branched alkyl of up~.to 4 carbon
atoms, X denotes chlorine or bromlne, and A deno~es an-azole ring
containlng 1 to 4 nl~rogen atoms which is attached vla ~ ring
nitrogen atom and may be mono~ or polysubstituted by halogen,
phenyl, alkyl, aikoxy, alkylthio or per~luoroalkyl, each of up
to 4 car~on atoms, cyano~ carboxy, carbalkoxy of up to 4 carbon
atoms in the alkoxy, or alkanoyl of up to 4 carbon atoms, or A
denotes a salt of an azole containing 2 or 3 nitrogen atoms, have
an excellent herbicidal action, but cause damage to crops ~uch
as Indian corn and Gramineae. . -~
.. . . . . ... ....
B
3~35
- 2 - O.Z. 0050/033324
It was therefore the object of the invention to provide
antagonistic agents which o~fset this poor tolerance of herbici-
dal acetanilides by certain crop plants.
Antagonistic agents (antidotes) are chemical compounds
as a result o~ the presence of which the tolerance, by certain
crop plants, of non-selective or insufficiently selective
herbicidal active ingredients is increased without their
action on unwanted plants being impaired.
Herbicidal agents containing, in addition to chloroacet-
anilides as herbicidal active ingredients, antagonistic dichloroacetamides have been disclosed in U.S. 4~053,297 and German
Laid-Open Applications DE-OS 2,218,097 and 2,402,983. Dichloro-
acetamides in which the 2 substituents on the nltrogen atom
form, with it, a heterocyclic ring which may contain a further
hetero atom and is unsubstituted or substituted by alkyl are
mentioned inker alia in these publications as possible anti-
dotes. N-dichlor-oacetyl-2,2-dimethyl-1,3-oxazolidine is given
as an example of this class of compounds.
However 9 German Laid-Open Application DE-OS 2,218,097
2C only recommends this antagonistic compound in combination
with herbicidally active thiolcarbamates, whereas it is known
from German Laid-Open Application DE-OS 2,402,983 and
U.S. 4,053g297 that N-dichloroacetyl-2,2-dimethyl-1,3-oxa-
zolidine is suitable as an antidote for reducing damage
caused to Indian corn by herbicidally active chloroacetanilides.
In addition to the chloroacetyl group 9 these chloroacet-
anilides bear on the nitrogen substituted alkyl 9 alkoxyalkyl,
alkenyloxyalkyl or cycloalkyloxyalkyl radicals or oxygen-
~L~33~1~333,5
- 3 - O.Z. 0050/033324
and/or sulfur-containing saturated rings attached via a
methylene group.
We have now ~ound that N-dichloroacetyl-2,2-dimethyl-1,3-
-oxazolidone is suitable for increasing the tolerance by crop
plants of herbicidal substituted acetanilides of the formula I.
Herbicidal agents containing at least one substituted acet-
anilide of the ~ormula I and N-dichloroacetyl-2,2-dimethyl-
-1,3-oxazolidine may be employed without di~ficutly in
Indian corn. The good herbicidal action of the acetanilides
is unimpaired, and damage to the crop plants is eliminated.
Acetanilides whose tolerance by crop plants can be
increased by N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine
are those of the formula I in which R is hydrogen, alkyl of a
maximum of 5 carbon atoms, such as methyl 9 ethyl, n-propyl 9
isopropyl, n-butyl, sec-butylg isobutyl, tert-butyl, linear
and branched pentyl, and alkoxy o~ a maximum of 5 carbon
atoms, such as methoxy, ethoxy, propoxy9 butoxy and pentoxy;
R1 and R2 are hydrogen, halogen, such as fluorine,
chlorine, bromine and iodine, alkyl o~ a maximum of 5 carbon
2C atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl,
sec-butyl, isobutyl, tert-butyl, linear and branched pentyl,
and alkoxy of a maximum of 5 carbon atoms, such as methoxy,
ethoxy, propoxy, butoxyj and pentoxy;
R2 together with R is an alkylene chain of a maximum of
6 carbon.atoms, linked in the o-position and unsubstituted or
substituted by alkyl o~ a maximum of 4 carbon atoms, e.g.,
ethylene, trimethylene, tetramethylene, 1-methyltrimethylene~
1,1 dimethyltrimethylene, and 1,1-dimethyltetramethylene;
~L~3~35
- 4 - OOZ. 0050/033324
X is chlorine, bromine or iodine3 pre~erably chlorine;
A is an azole attached via a rin~ nitrogen atom, e.g~,
pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole,
and tetrazole, which be mono- or polysubstituted by halogen,
phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of
up to 4 carbon atoms, cyano, carboxy, or carbalkoxy with up
to 4 carbon atoms in the alkoxy, or alkanoyl of up to 4 carbon
atoms, the substituents being identical or different, such as
2,6-dimethylpyrrole, tetramethylpyrrole, 3(5)-methylpyrazole,
4-methylpyrazole, 3(53-ethylpyrazole, 4-ethylpyrazole, 3(5)-iso-
propylpyrazole, 4-isopropylpyrazole, 3,5-dimethylpyrazole,
315-dimethyl-4-acetylpyrazole, 3,5-dimethyl-4-propionylpyrazole,
3,4,5-trimethylpyrazole, 3(5)-phenylpyrazoleg 4-phenylpyrazole,
3,5-diphenylpyrazole, 3(5)-phenyl-5(3)-methylpyrazole, 3(5)-
-chloropyrazole, 4-chloropyrazole, 4-bromopyrazole, 4-iodo-
pyrazole, 3,4,5-trichloropyrazole, 3,4,5-tribromopyrazole,
3,5-dimethyl-11-chloropyrazole, 3,5-dimethyl-4-bromopyrazole,
4-chloro-3(5)~methylpyrazole, 4-bromo-3(5)-methylpyrazole,
4-methyl-3,5-dichloropyrazole, 3(5)-methyl~4,5(3)-dichloro-
2C pyrazole, 3(5)-chloro-5(3)-me~hylpyrazole, 4~methoxypyrazole,
3(5)-methyl-5(3~-methoxypyrazole, 3(5)-ethoxy-4,5(3)-dimethyl-
pyrazole, 3(5)-methyl-5(3)~trifluoromethylpyrazole, 3,5-bis-
-trifluoromethylpyrazole, 3(5)-methyl-5(3)-carbethoxypyrazole,
3,5-bis-carbethoxypyrazola, 3,4,5-triscarbethoxypyrazole,
~(5)-methyl-5(3) methylthio-4-carbethoxypyraæola, 4-methyl-3,5-
-biscarbethoxypyraæole, 4-cyanopyrazole, 4-methoxy-3,5-di-
chloropyrazole~ 4,5-dichloroimidazole, 2-ethyl-4,5-dichloro-
imidazole, 2-methyl-4,5-dichloroimidazole, 3(5)-methyl-1,2,4-
` - 5~-~3~5 O.Z. 0050/03332~
-triazole~ 3,5-dimethyl-1,2,4-triazole, 3(5)-chloro-1,2,4-
-triazole, 3(5)-bromo-1,2,4-triazole, 3(5)-chloro-5(3)-methyl-
-192,4-triazole, 3,5-dichloro-1,2,4-triazole, 3,5-dibromo-
-1,2,4-triazole, 3(5)-chloro-5(3)-cyano-1,2,4-triazole,
3(5) chloro-5(3)-phenyl-1,2,4-triazole, 3(5)-chloro-5(3)-
-carbomethoxy-1,2,4-triazole, 3(5)-methylthio-1~2,4-triazole,
4(5)-methyl-1,2,3~triazole, 4,5-dimethyl-1,2,3-triazole,
4(5)-phenyl-1,2,3-triazole, 4(5)-chloro-1,2,3-triazole,
1,2,3-triazol-4(5)-yl-carboxylic acid ethyl ester, 1,2,3-tri~
azol-4,5-yl-dicarboxylic acid dimeth~l ester, 5-methyltetra-
zole, 5-chlorotetrazole, and tetrazolyl-5-carboxylic acid ethyl
ester.
Furthermore, the radical A may, when the optionally sub-
stituted azole contains 2 or 3 nitrogen atoms, also be attached
in a salt-like manner to one of the usual strong inorganic or
organic acids, e.g., hydrochloric acid, hydrobromic acid,
nitric acid, sulfuric acid, tetrafluoboric acid, fluosulfonic
acid, and ~ormic acid, a halogenated carboxylic acid, e.g.,
trichloroacetic acid, an alkanesulfonic acid, e.g., methane-
2C ulfonic acid, a halogenated alkanesulfonic acid, e.g., tri-
fluoromethanesulf'onic acid and per~luorohexanesul~onic acid,
and an arylsul~onic acid, e.g. dodecylbenzenesulfonic acid.
Pre~erred acetanilides are those which bear methyl or
ethyl in the 2- and 6-positions on the phenyl ring and hydrogen,
methyl or ethyl in the 3-position; sui~able azoles are pyrazole,
imidazole, triazole and tetrazole, which are unsubstituted or
substituted by lower alkyl, alkoxy, carbalkoxy, cyano or
halogen.
~3~C13S
- 6 - O.Z. 0050/03332
In particular, the herbicidal agents accordin~ to the
invention contain the following acetanilides:
2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide,
2-chloro-2'-methyl-6'-ethyl-N-(pyrazol-1-yl-methyl)-acet-
anilide, 2-chloro-2',6'-dimethyl-N-(4-methylpyrazol-1-yl-
methyl)-acetanilide, 2-chloro-2'-methyl-6-ethyl-N-(4-methoxy-
pyrazol-1-yl-methyl) acetanilide, 2-chloro-2'-methyl-6'-
ethyl-N-(3(5)-methylpyrazol-1-yl)-acetanilide, 2-chloro~2',
6'-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-acetanilide,
2-chloro~2~6~-di~methyl-N-(l~2~4-triazol-l-yl-methyl)-acet
anilide~ 2 chloro-2',6'-dimethyl-N-(4-chloropyrazol-1-yl-
-methyl)-acetanilide, 2-chloro-2',3',6'-trimethyl-N-(pyrazol-
-1-yl-methyl)-acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(3,5-
~dimethylpyrazol-1-yl-methyl)-acetanilide, 2~chloro-2',6'-di-
ethyl-N-~3~5-dimethylpyrazol-l-yl-methyl)-acetanilide~ 2-chloro-
-2t~3~6~-trimethyl-N-(3~5-dimethylpyrazol-l-yl-meth7l)-acet-
anilide, 2-chloro-2',6'-diethyl-N-(4-methylpyrazol-1-yl-methyl)-
~acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(4-methylpyrazol-
-1-ylmethyl)-acetanilide~ 2~chloro-2',3',6~-trimethyl-N~(4-me-
2C thylpyrazol-1-yl-methyl)-acetanilide, 2-chloro-2',6'-dim~thyl-
-N-(3~(5)-methylpyrazol-l yl-methyl)~acetanilide, 2-chloro-
-2',6'-diethyl-N-(3-(5)-methylpyrazol-1-yl-methyl)-ac_tanilide,
2-chloro-2',6'-dimethyl~N-(4-methoxypyrazol-1-yl-methyl)-acet-
anilide~ 2-chloro-2'g6'-diethyl-N (pyrazol-1-yl-methyl)-acet~
anilide, 2-chloro-2l,6'-dimethyl-N-(4,5-dichloroirnidazol-1-yl~
-methyl)-acetanilide, 2-chloro-2'-methyl-6'-ethyl-N-(4,5-di-
chloroimidazol-1-yl-methyl)-acetanilide, 2-chloro-2'-methyl-
-6'-ethyl~N-(2-ethyl-l,5-dichloroimidazol-1-yl~methyl)-acet-
- 7 - O.Z. 0050/033324
anilide, 2-chloro-2'~6'-diethyl-N-(4,5 dichloroimidazol-1-yl-
-methyl)-acetanilide, 2-chloro~2'-methyl-6'-ethyl-N-(1,2,4-tri-
azol-l-yl-methyl)-acetanilide~ 2-chloro-2',6'-diethyl-N-(1,2,4-
~triazol~1-yl-methyl)-acetanilide and 2-chloro-2',3',6'-tri-
methyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide.
A particularly pre~erred agent according to the invention
contalns, in addition to N-dichloroacetyl-2,2-dimethyl-1,3-
-oxazolidine, 2-chloro-21,6'-dimethyl-N-(pyrazol-1-yl-methyl)-
-acet~nilide as herbicidal active ingredient.
The acetanilides of the ~ormula I are disclosed in German
Laid-Open Applications DE-OS 25648,oo8 and DE-OS 2,74~,396.
They may be obtained by reaction of 2-halo-N-halomethylacet-
anilides of the formula II with a lH-azole of the formula H-A
in accordance with the ~ollowing equation:
R R
~ /CH2-X I CH2-A
</ \~N~ ~ H-A ~ + HX
R2/~/ CO-CH2-X R2 /~/ CO-CH2-X
Rl R
II
2C
R, R1, R2 and X have the above meanings and A denotes an azole
linked via a rin~ nitrogen atom and which may be mono- or poly-
substituted by halogeng phenyl, alkyl, alkoxy, alkylthio or
perfluoroalkyl, each of up to 4 carbon atoms, cyano, carboxy,
carbalkoxy o~ up to 4 carbon atoms in the alkoxy, or alkanoyl
of up to 4 carbon atoms.
The manu~acture o~ N-dichloroacetyl-2,2-dimethyl 1~-
-oxazolidine i8 disclosed in German Laid-Open Applications
DE-OS 2,218,097 and DE-OS 2,402,98~.
1l~3~g~3~
- 8 - O.Z. 0050/033324
N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine itself
has scarcely any in~luence, if at all, on the germination
and growth of crop and unwanted plants, even at application
rates well above those required for an antagonistic sffect.
However, it is capable of considerably reducing the phyto-
toxicity of the herbicidal acetanilides of the formula I
to crop plants such as Indian corn, or of eliminating it
completely.
In these case of herbicidal acetanilides which are
less a~gressive to crop plants, low additions of N-dichloro-
ac~tyl-2,2-dimethyl-1,3-oxazolidine are suf~icient. The ratio
of acetanilide to N-dichloroacetyl 2,2-dimethyl-1,3-oxa-
zolidine may vary within wide limits, and depends on the
acetanilide. Suitable ratios of herbicidal active ingre-
dient to N-dichloroacetyl-2,2-dimethyl-1~3-oxazolidine are
- from 1:2 to 1:0~01 parts by weight.
Acetanilides and antagonistic compounds may be in-
corporated into the soil either together or separately and
before or after sowing. With acetanilides of the formula I~
2~ the commonest method is to apply them to the surface of the
soil immediately after sowing, or in the period between sowing
and emergence o~ the young plants. It is also possible to
apply them during emergence and shortly therea~ter. In each
instance, the antagoniætic agent may be applied simultaneously
with the herbicidal active ingredient~ It is also possible to
apply the compounds separately - either the antagonist ~irst
and then the herbicidal active ingredient, or vice versa -
provided that, if the herbicidal active ingredient is applied
:1 ~31~3~
- g O.Z. 0050/033324
first, not too much time elapses be~ore the antagonist is
applied as otherwise the crop plants may be damaged. The
active ingredient and antagonist may be suspended, emulsified
or dissolved in a spray liquor or may be in granular ~orm, and
may be formulated together or separately. It is also feasible
to treat the seed with the antagonist befora sowing. The
herbicidal active ingredient is then applied on its own in the
usual manner.
The novel herbicidal agents may contain, in addition to
acetanilide and N-dichloroacetyl~2,2-dimethyl-1,3-oxazolidine,
other herbicidal or growth-regulating active ingredients of
di~ferent chemical structure, e.g., 2-chloro-4-ethylamino-6
-isopropylamino-1~3,5-triazine, without the antagonistic
effect being impaired.
The agents according to the invention, or, when applied
separately~ the herbicidal active ingredients and the antidote
are applied for instance in the form of directly sprayable
solutions, powders, suspensions (including high-percentage
aqueous~ oily or other suspensions), dispersîons, emulsions,
2C oil dispersionsg pastes, dusts, broadcasting agents, or granules
by spraying, atomizing, dusting, broadcasting or watering. The
~orms o~ application depend entirely on the purpose for which
the agents are being used; in any case they should ensure
very ~ine distribution of the agents according to the invention
or their individual components.
For the preparation of solutions, emulsions, pastes and
oil dispersions to be sprayed direct, mineral oil ~ractions o~
medium to high boiling point, such as kerosene or diesel oil,
- ~3~ 5
- 10 - O.z. 0050/033324
further coal-tar oils, and oils of vegetable or animal origin~ -
aliphaticg cyclic and aromatic hydrocarbons such as benzene,
toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
naphthalenes and their derivatives such as methanol, ethanol,
propanol, butanol, chloroform, carbon tetrachloride, cyclo
hexanol, cyclohexanone, chlorobenzene, isophorone, etc., and
strongly polar sol~ents such as dimethylformamide, dimethyl-
sulfoxide, N-methylpyrrolidone, waterg etc. are suitable.
Aqueous formulations may be prepared from emulsion con-
centrates~ pastes, oil dispersions or wettable powders by
adding water. To prepare emulsions~ pastes and oil dispersions
the herbicidal active ingredient and/or antidote, as such or
dis~olved in an oil or solventg may be homogenized in water by
means of wetting or dispersing a~ents, adherents or emulsifiers.
Concentrates which are suitable for dilution with water may be
prepared ~ om herbicidal active ingredient and/or antidoteg
wetting agent, adherent, emulsifying or dispersing agent and
possibly sol~ent or oil.
Examples of surfactants are: alkali metal, alkaline earth
2C metal and ammonium salts of ligninsulfonic acid, naphthalene-
sulfonic acids, phenolsulfonic acids, alkylaryl sulfonates,
alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline
earth metal salts of dibutylnaphthalenesulfonic acidg lauryl
ether sulfate, fatty alcohol sulfates, alkali metal and alkaline
earth metal salts o~ fatty acids, salts of sulfated hexadecanols,
heptadecanols, and octadecanols, salts of sulfated fatty alco-
hol glycol ethers, condensation products of sulfonated naphtha-
~3~3S
0 Z. 0050/033324lene and naphthalene derivatives with formaldehyde, condensation
products of naphthalene or naphthalenesulfonic acids with phenol
and ~ormaldehyde~ polyoxyethylene octylphenol ethers, ethoxyl-
ated isooctylphenol, ethoxylated octylphenol and ethoxylated
nonylphenol~ alkylphenol polyglycol ethers, tributylphenyl
polyglycol ethers, alkylaryl polyether alcohols, isotridecyl
alcohol3 fatty alcohol ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxy-
propylene, lauryl alcohol polyglycol ether acetal, sorbitol
esters, lignin, sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by
mixing or grinding the herbicidal active ingredient and/or anti-
dote wit~ a solid carrier.
Granules, e.g., coated, impregnated or homogeneous gra-
nules, may be prepared by bonding the active ingredients to
solid carriers. Examples of solid carriers are mineral earths
such as silicîc acid, silica gels, silicates, talc, kaolin,
Attaclay, limestone, lime, chalk, bole, loessS clay, dolomite,
diatomaceous earth, calcium sulfate, magnesium sulfate, mag-
2C nesium oxide, ground plastics, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate~ and ureas, and
vegetable producks such as grain flours, bark meal, wood meal,
and nutshell meal, cellulosic powders, etc.
The formulations contain from 0.1 to 95, and preferably
0.5 to 90, % by weight of herbicidal active ingredient and/or
antidote. Application rate3 are from 0.2 to 5 kg of herbicidal
active ingredient per hectare. This amount of herbicidal
active ingredient is applied, together or separately, with
~IL3~33~
- 12 - 0050/033324
such an amount of antidote to give a ratio of herbicidal
active ingredient to antagonist of from 1:2 to 1:0.01 parts
by weight.
Examples of formulations are given below.
I. 40 parts by weight of a mixture of 4 parts by weight
of 2-chloro-2l,6'-dimethyl-N-(pyrazol-l-yl-methyl)-acetamide
and 1 part by weight of N-dichloroacetyl-2,2-dimethyl-1,3-
-oxazolidine is intimately mixed with 10 parts of the sodium
salt of a phenolsulfonic acid-urea-formaldehyde condensate,
2 parts of silica gel and 48 parts of water. A stable~
aqueous dispersion is obtained. Dilution in 1003000 parts by
weight of water gives an aqueous dispersion containing
0.04 wt% of the mixture of active ingredient + antidote.
II. 3 parts by weight of a mixturs of 1 part by weight of
2-chloro-2',6'-dimethyl-N-(pyrazol-l-yl-methyl)-acetanilide
and 1 part by weight of N-dichloroacetyl-2,2-dimethyl-1,3-
-oxaæolidine is intimately mixed with 97 parts by weight
of particulate kaolin. A dust is obtained containing 3% by
weight of the mixture of active ingredient + antidote.
2C III. 30 parts by weight of a mixture of 1 part by weight of
2~chloro 2'-methyl-6'-ethyl-N-~1,2,4-triazol-1-yl-methyl)~acet-
anilide and 1 part by weight of N-dichloroacetyl-2,2-dimethyl-
-1,3~oxazolidine is intimately mixed with a mixture consisting
of 92 parts by weight of powdered silica gel and 8 parts by
weight of para~in oil which has been sprayed onto the surface
of this silica gel. A ~ormulation is obtained having good
adherence.
~l3~3~
- 13 - O.Z. 0050/033324
IV. 20 parts by weight of a mixture of 8 parts by weight of
2-chloro-2'-methyl~5~-ethyl~N-(pyrazol-1-yl-methyl)-acet-
anilide and 1 part by weight of N-dichloroacetyl~2,2-dimethyl-
-1,3-oxazolidine is intimately mixed with 2 parts of the
calcium salt of dodecylbenzenesulfonic acid, 8 parts of
a fatty alcohol polyglycol ether, 2 parts of the sodium
salt of a phenolsulfonic acid-urea-formaldehyde condensate
and 68 parts of a paraffinic mineral oil. A stable oily dis-
persion is obtained.
V. 20 parts by weight of a mixture of 10 parts by weight
of 2-chloro-2',6 7 -dimethyl-N-(4l5-dichloroimidazol-1-yl-
-methyl~-acetanilide and 1 part by weight of N-dichloro~
acetyl-2,2-dimethyl-1,3 oxazolidine is dissol~ed in a mix-
ture consisting of 40 parts by weight o~ cyclohexanone,
30 parts by weight of isobutanol, 20 parts by weight of the
adduct of 7 moles of ethylene oxide to 1 mole of isooctyl-
phenol, and ~0 parts by weight of the adduct oP 40 moles of
ethylene oxide to 1 mole of castor oil. By pouring the solution
into 100,000 parts by weight of water and finely distributing
2C it therein, an aqueous dispersion is obtained containing 0.02%
by weight of the mixture of active ingredient ~ antidote.
Gr~enhouse experiments show that the use of the herbicidal
agents according to the invention increases the tolerance of
the herbicidal acetanilides by the crop plants without the
herbicidal action being affected.
Plastic boxes 51 cm long, 32 cm wide and 6 cm deep were
filled with loamy sand (pH:6 to 7) containing about 1.5% humus.
L33~
- 14 - O.Z. 0050/033324
Indian corn (Zea mays) was sown sha]low, in rows, in this
substrate. Echinochloa crus-galli was scattered at random
as unwanted plant~ The non-sterilized soil also additionally
contained viable weed seeds which contributed to the weed
population. A field with crop plants growing in it and in-
fested with weeds was thus simulated.
The active ingredients and the antagonist were applied
separately and in the mixtures given below. They were emul-
si~ied or suspended in water as vehicle and the liquor was
sprayed through finely distrihuting nozzles onto the soil
surface, either immediately after sowing or prior to emergence
of the test plants After sowing and treatment the boxes were
sprinkler-irrigated and covered with transparent plastic hoods
until the plants emerged. These measures ensured that the
plants germinated and took root uniformly. The boxes were set
up in the greenhouse at from 18 to 30C. These greenhouse
experiments were monitored until 3 to 5 Indian corn leaves
had developed.
The scale for assessing the action of the agents was 0
2C to 100, 0 denoting normal emergence and development of the
plants, with reference to the untreated control, and 100
denoting non-germination or withering of the plants. It
should be borne in mind here that, for instance in Indian
corn, odd crippled or retarded plants may occur even under
completely normal conditions and without any chemical treat-
ment.
~L~3~3S
- 15 - O.Z. 0050/033324
The following table shows the extent to which N~dichloro-
acetyl 2,2 dimethyl-1,3-oxazolidine increases the tolerance
by Indian corn of acetanilides of the ~ormula I, e.g.,
2-chloro-2',6'-dimethyl-N-(pyrazol 1-yl-methyl)-acetanilide.
2C
- 16 -0 ~ Z . 0050/033324
. ~'
~ ~ ~ o, o~ o~ ~ 8
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