HERBICIDALLY ACTIVE CHLORACETANILIDES, A PROCESS FOR THEIR MANUFACTURE AND THEIR USE

TRADUCTION NON-DISPONIBLE

English Abstract

ABSTRACT OF THE DISCLOSURE
Herbicidally active chloracetanilides of the formula I
<IMG> (I)
(wherein R1, R2 and R3 each represents H, C1-4-alkyl, halogen or
F3C, R4 represents C1-6-alkyl and n is I, 2 or 3) and their
manufacture, The compounds of the formula I have both a
herbicidal and a growth-regulating action, and accordingly may
be made up with suitable carriers into herbicidal preparations
and may be used for treating living plants and areas of land.

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A chloracetanilide of the general formula I
<IMG>
(I)
in which R1, R2 and R3 each represents a hydrogen atom, an alkyl
group containing 1 to 4 carbon atoms, a halogen atom or a
trifluoromethyl group, R4, represents an alkyl group containing
1 to 6 carbon atoms and n represents 1, 2 or 3.
2. A compound as claimed in claim 1, wherein R1 and
R2 each represents an alkyl group containing 1 to 4 carbon
atoms, R3 represents a hydrogen atom, R4 represents an alkyl
group containing 1 to 4 carbon atoms and n represents 1 or 2.
3. Chloracetic acid [N-(3,6-dioxaheptyl)-2,6-dimethyl-
anilide].
4. Chloracetic acid [N-(3,6-dioxaoctyl)-2-methyl-
anilide].
5. Chloracetic acid [N-(3,6-dioxaheptyl)-anilide].
6. Chloracetic acid [N-(3,6-dioxaheptyl)-2,6-diethyl-
anilide].
7. Chloracetic acid IN-(3,6-dioxaheptyl)-2-methyl-
anilide].
8. Chloracetic acid [N-(3,6-dioxaoctyl)-2,6-dimethyl-
anilide].
9. Chloracetic acid [2,6-diethyl-N-(3,6-dioxaoctyl)-
anilide].
10. Chloracetic acid [2-chloro-N-(3,6-dioxaoctyl)-6-
methylanilide].
13

11. Chloracetic acid [2-chloro-N-(3,6-dioxaheptyl)-
6-methylanilide].
12. Chloracetic acid [N-(3,6-dioxaoctyl)-2-methyl-
anilide].
13. Chloracetic acid [2,6-dimethyl-N-(3,6,9-trioxa-
decyl)-anilide].
14. Chloracetic acid [2,6-diethyl-N-(3,6,9-trioxa-
decyl)-anilide].
15. Chloracetic acid [2-methyl-N-(3,6,9-trioxadecyl)-
anilide].
16. Chloracetic acid [2,6-dimethyl-N-(3,6,9,12-tetra-
oxytetradecyl)-anilide].
17. Chloracetic acid [2,6-dimethyl-N-(3,6,9-trioxaun-
decyl)-anilide].
18. Chloracetic acid [2-ethyl-6-methyl-N-(3,6-dioxa-
heptyl)-anilide].
19. A process for the manufacture of a compound of
the general formula I given in claim 1, in which R1, R2, R3, R4
and n have the meanings given in claim 1, wherein an aniline
of the general formula II
<IMG> (II)
in which R1, R2 and R3 have the meanings given above, is
reacted with a compound of the general formula III
X-OH2CH2-(OCH2CH2)n-OR4 (III),
in which R4 and n have the meanings given above and X represents
a hydroxyl group, a halogen atom or a 4-CH3-C6H4-SO2-O- group,
the reaction when X represents a hydroxyl group being carried
out under pressure and when X represents a halogen atom or a 4-
CH3-C6H4-SO2-O- group being carried out at a temperature within
14

the range of from 20 to 200°C , and the resulting reaction
product of the general formula IV

<IMG>
(IV)
in which R1, R2, R3, R4 and n have the meanings given above, is
reacted in the presence of an acid acceptor with chloracetyl
chloride.
20. A process as claimed in Clalm 19, wherein the molar
weight ratio of the aniline of the general formula II to the
compound of the general formula III is within the range of from
2:1 to 3:1.
21. A process as claimed in Claim 19, wherein when X
represents a hydroxyl group, the reaction with the compound of
the general formula III is carried out in the presence of water
and a catalyst.
22. A process as claimed in Claim 21, wherein the
catalyst is a nickel catalyst.
23. A process as claimed in Claim 19 or 20, wherein
when X represents a halogen atom or a 4-CH3-C6H4-SO2-O-group, the
reaction with the compound of the general formula III is carried
out in the presence of an inert solvent.
24. A process as claimed in Claim 19, 20 or 21, wherein
in the reaction between the product of the general formula IV and
the chloracetyl chloride either these reactants are used in equi-
molar quantities or the chloroacetyl chloride is used in excess.
25. A process as claimed in Claim 19, 20 or 21, wherein
the reaction with the chloroacetyl chloride is carried out in the
presence of an organic solvent at a temperature within the range
of from -10 to 105°C.
26. A method of protecting a living plant against
16

weeds, wherein the area in the vicinity of the living plant is
treated with a compound of the general formula I given in Claim
1, in which R1, R2, R3, R4 and n have the meanings given in Claim
1.
27. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 2.
28. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 3 or 4.
29. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 5 or 6.
30. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed inClalm 7 or 8.
31. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 9 or 10.
32. A method as claimed in Claim 26, wherein tile area
is treated with a compound as claimed in Claim 11 or 12.
33. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 13 or 14.
34. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 15 or 16.
35. A method as claimed in Claim 26, wherein the area
is treated with a compound as claimed in Claim 17 or 18.
36. A method as claimed in Claim 26, wherein a single
compound of the general formula I is used for the treatment in an
amount within the range of from 0.5 to 5 kg per hectare.
37. A method as claimed in Claim 26, wherein two or
more compounds of the general formula I are used for the treatment
in a total amount within the range of from 0.5 to 5 kg per hectare.
38. A method of protecting a crop area against weeds,
wherein the crop area is treated with a compound of the general
formula I given in Claim 1, in which R1, R2, R3, R4 and n have
the meanings given in Claim 1.
17

39. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 2.
40. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 3 or 4.
41. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 5 or 6.
42. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 7 or 8.
43. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 9 or 10.
44. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 11 or 12.
45. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 13 or 14.
46. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 15 or 16.
47. A method as claimed in Claim 38, wherein the crop
area is treated with a compound as claimed in Claim 17 or 18.
48. A method as claimed in Claim 38, wherein a single
compound of the general formula I is used for the treatment in an
amount within the range of from 0.5 to 5 kg per hectare.
49. A method as claimed in Claim 38, wherein two or
more compounds of the general formula I are used for the treatment
in a total amount within the range of from 0.5 to 5 kg per hectare.
50. A method as claimed in Claim 38, wherein the crop
is a cotton, ground-nut, rape, kale, cauliflower, soya bean, pea,
sugar beet, spinach or lettuce crop.
51. A method of regulating the growth of a living
plant, wherein the living plant is treated with a compound of the
general formula I given in Claim 1, in which R1, R2, R3, R4 and n
have the meanings given in Claim 1.
52. A method as claimed in Claim 51, wherein the plant
18

is treated with a compound as claimed in Claim 2.
53. A method as claimed in Claim 51 , wherein the plant
is treated with a compound as claimed in Claim 3 or 4.
54. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 5 or 6.
55. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 7 or 8.
56. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 9 or 10.
57. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 11 or 12.
58. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 13 or 14.
59. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 15 or 16.
60. A method as claimed in Claim 51, wherein the plant
is treated with a compound as claimed in Claim 17 or 18.
19

Description

~ 0~ 6 ~ ~
The present invention is concerned with new herbicidally
active chloracetanilides, w~th a process for the manufacture
of these compounds and also with their use~
Halogeno-acetanilide derivatives having a herbicidal
action are already known (see United States Patent Specification
No. 3,547,620). Howevert they have only a narrow range of action
and their action is strongly dependent on the soil.
The prohlem upon which the present invention is based
has therefore been to develop a herbicide, which has a wide range
of action and is not dependent on the soil.
This problem ls solved in accordance with the
present invention by the compounds of the general formula I,
as defined below.
The present invention accordingly provides compounds
of the general formula I
oH2oH2 (~2CH2)n~R4
/ \ G~H
~0
~ 2
in which Rl, R2 and R3 each represents a hydrogen atom, an alkyl
group containing 1 to 4 carbon atoms, a halogen atom or a
trifluoromethyl group, R4 represents an alkyl group containing
1 to 6 carbon atoms and n represents 1, 2 or 3.
The meanings of the symbols Rl, R2 and R3 may be the
same or different.
The compo~mds of the present invention are distinguished
by a broad soil-herbicidal action. They can be used for
combating mono- and di-cotyledonous weeds.
Weeds that can be combated by means of these compounds
by the pre-emergence method are, for example, ~llium, Solanum,

99~;
Senecio, Matricarla, Galium, Polygonum, Trifolium, Escholtzia, .:
Di~italis, Phacella, Sorghum, Echinochloa, Setaria, Digitaris,
Cyperus, Poa, Agrostls, sromus~ Lolium, Phleum, Dactylis and
Festuca.
For combating weeds there are generally used applica-
tion quantities within the range of from 0.5 kg of active
substance per hectare to 5 kg of acti~e substance per hectare.
The aCtiYe compounds of the present invention have thereby also
proved to be surprisingly selectively active in crops of useful
plants, for example cotton, ground-nut, rape, kale, cauliflower,
soya bean, pea-, sugar beet, spinach and lettuce crops. When two
or more compounds of the general formula I are used the range of
0.5 to 5 kg per hectare refers of course to the total amount
appIied of these compounds.
The active compounds o~ the present invention have a
further advantage in that they also exhibit growth-regulating
properties.
As the further technically valuable changes in the
de~elopment of plants caused by the compounds of the present :~ :
inventlon there may be mentioned, for exam.ple, retardation of ~ :
vertical growth, retardation of root development., stimulation
: of the growth of bud shoots or side-shoots from low-lying buds, ..
intensification of the formation of plant colouring matters and
improvement in the storage capacity of plant components.
The present invention accordingly also provides a
herbicidal preparation which comprises a compound of the general .
formula I, in admixture or con~unction with a suitable carrier.
The preparation may of course contain one or more compounds
of the general formula I. ~ .
The present invention further provides a method of
protecting a living plant against weeds, wherein the area in the
vicinity of the Iiving plant is treated with a compound of the
- ~ . : -, . .. .. . .

general formula I.
The present invention further provides a method of
protecting a crop area against weeds, wherein the crop area is
treated with a compound of the general formula I.
The present invention further provides a method of
reyulating the growth of a living plant, wherein the liviny
plant is treated with a compound of the general formula I.
The present invention further provides a pack which
comprises a compound of the yeneral formula I toyether with
instructions for its use as a herbicide and/or for regulatiny
the yrowth of a living plant.
The compounds of the present invention may be used
either alone, or in admixture with one another or with other
active substances. If desired, other plant protectiny or pest-
combating agents may be added depending on the purpose desired.
If it is lntended to broaden the range of ac-tion
other herbicides may also be added. As suitable herbicidally
active co-components there may be mentioned, for example, active
substances belonging to the groups of triazines, aminotriazoles,
anllides, diaziDes, uracils, aliphatic carboxylic acids and
halogeno-carboxyllc acids, substituted benzoic acids and aryloxy-
carboxylic acids, hydrazides, amides,
nitriles, esters of such
carboxylic acids, carbamic acid esters and thiocarbamic acid
esters, ureas, l,3,6-trichlorobenzyloxy--propanil and thiocyan-
ate-containing agents. Among other additives there are to be
understood, for example, non-phytotoxic additives, which give a
synergistic increase in action with herbicides, for example
wetting agents, emulsifiers, solvents and oily additives.
The active compounds of the general formula I or mixtures
thereof are advantageously used in the form of herbicidal
preparations, for example powders, strewable preparations,

` ~ :
granules, solutions, emulsions or suspensions, wi-th the addition
Qf liquid and/or solid vehicles or diluents and, if desired,
of surface-active agents, for example wetting, adherent,
emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water,
aliphatic hydrocarbons, aromatic hydrocarbons, for example
benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl
sulphoxide and dimethylformamide, and also mineral oil ~ractions.
As solid carriers there are suitable, for example,
mineral earths for example tonsil, sllica gel, talcurn, kaolin,
attaclay, limestone and silicic acid, and vegetable products,
for example meals.
As surface-active agents there may be mentioned, for
example, calcium lignin sulphonate, polyoxyethylene alkylphenol
ethers, naphthalene sulphonic acids an~ salts thereof, phenol
sulphonic acids and salts thereof, formaldehyde condensates,
fatty alcohol sulphates and also substituted ben~ene sulphonic
acids and salts thereof.
The total amount of the active substance or substances
in the various herbicidal preparations may vary within wide
limits. For example, the preparations may contain approximately
5 to 95~ by weight of active substance(5), approximately 95 to --
5~ by weight of li~uid or solid carrier and, if desired, also
up to 20% by wei~ht of sur~ace-active agent(s).
The active substances may be applied in the usual
manner, for example with water as carrier in quantities of spray
liquor of approximately 100 to 1000 litres per hectare. It is
also possible to apply the active substances by the so-called
low-volume method and ultra-low-volume method and it is also
possible to apply them in the form o~ so called microgranules.
As substituents represented by Rl , R2 and R3 in the
general formula I there may be mentioned, for example, methyl,
-5-
.:

ethyl, n-propyl, isopropyl, _-butyl, sec.-butyl, isobutyl,
tert.-butyl, fluoro, chlo.ro, bromo, iodo and trifluoromethyl
substituents.
The symbol R4 may represent, for example, a methyl
ethyl, propyl, isopropyl, n-butyl, sec.-butyl, isobutyl,
tert.-butyl, n-pentyl or n-hexyl group.
Among the compounds of the present invention that
are dist~nguished-by an outstanding action are especially
those of the general formula I in which Rl and R2 have identical :
or different meanings and each represents an alkyl group
containing 1 to 4 carbon atoms, R3 represents a hydrogen atom,
R4 represents an alkyl group containing l to 4 carbon atoms and ~
n represents the number 1 or 2. :
The hitherto unknown compounds of the yeneral formula
I may be prepared, for example, by the process of the present
invention, as defined below.
The present invention accordingly further provides
a process for the manufacture of a compound of the general
formula I, wherein an aniline of the general formula II
R~
: 1 '
2 (I~
J~R2
~3
in which Rl, R2 and R3 have the meanings given abovej is reacted,
preferably in the molar weight ratio within the range of from 2:1
to 3:1, with a compound of the general formula III
X-CH2CH2-(OCH2CH2)n-OR4 (III),
in which R4 and _ have the meanings given above and X represents
a hydroxyl group, a halogen atom or a 4-CH3-C6H~-SO2-O- group,
the reaction when X represents a hydroxyl group being carried out
: -6-

unaer pressure and, if desired, with the addition of water and a
catalyst, preferably a nickel catalyst, and when X represents a
halogen atom or a 4-CH3-C6~4-SO2-O- group being carried out at a
temperature within the range o~ from 20 to 200C, if desired
with the use of an inert solvent, for example an organic solvent
for example toluene or xylene, and the resulting reaction
product of the general formula IV
Rl ' R '
~ aH2~2~ ~2~2~n 4
~ ~ ~ (IV)
.
in which Rl, R2, R3, R4 and _ have the meanings given above, is
reacted wi-th chloracetyl chloride inthe presence of an acid
acceptor, for example an organic base, for example pyridine or
triethylamine, or an inorganic base, for example sodium hydroxide,
potassium hydroxide, sodium carbonate, potassium carbonate or
magnesium oxide, and, if desired, of an organic solvent at a
temperature within the range of from -lO to 105C. The final
reaction product may be isolated in a manner known per se.
In the reaction between the product of the general
formula IV and the chloracetyl chloride these reactants may be
used in equimolar quantities but preferably, however, the
chloracetyl chloride is used in excess.
The compounds of the present invention are generally
almost colourless, odourless, sparingly mobile liquids, which
readily dissolve in polar organic solvents, for example acetone,
dimethylformamide and dimethyl sulphoxide, and are practically
insoluble in water and gasoline.
The following Examples illustrate the invention.
Example 1 illustrates the manufacture of the compounds of the
,
~ -7-

present invention and Examples 2 and 3 illustrate the possible
uses and superior action of the compounds of the present
invention.
Example 1 `
Chloracetic acid [N-(3,6-diox ept~ 2,6-dimeth~lanilide].
A solution of 60.50 gm (0.5 mole) o 2,6-dime~hyl-
aniline and 68.50 gm (0.25 mole) of (para-tolyl)-(1,4,7-trioxa-
octyl)-sulphone in 100 ml of toluene was heated for 20 hours
under reflux. After cooling, water and 25 ml of a concentrated
solution of sodium hydroxide were added and, after dilution
with ethyl acetate, the organic phase was separated. It was !
then washed until almost neutral with water, dried over magnesium
sulphate and after filtration concentrated in vacuo.
The residue was distilled in vacuo, and N-(3,6-dioxa-
heptyl)-2,6-dimethylaniline having a boiling interval of 119 -
131~C (0.~ Torr) was obtained.
Yie~d: 32.44 gms = 58.1% of the theoretical yield.
Into a solution of 11.15 gms (0.05 mole) of N-(3,6-
dioxaheptyl)-2,6-dimethylàniline in 50 ml of ethyl acetate
were introduced 13.82 gms (0.1 mole~ of anhydrous potassium
carbonate. There were introduced into the stirred suspension
dropwise at 25 - 30C whi~e cooling with ice 11.29 gms (0.1 mole) -
of chloracetyl chlorlde, and the whole was further stirred
for one hour. The mixture was left to stand for a few hours
at room temperature. Water was then added and the mixture was
extracted by agitatlon several times with ethyl acetate. The
combined ethyl acetate phases were dried over magnesium
sulphate and, after filtration, concentrated in vacuo.
After drying at room temperature under a high vacuum
an almost colourless oil was obtained.
Yield: 12.23 gms (= 81.6~ of the theoretical yield)
of chloracetic acid ~N-(3,6-dioxaheptyl)-2/6-dimethyl-anilide].
-8-

96
nD = 1.5250.
The follow1ng compounds of the present invention can
be prepared in an analogous manner.
Name of the compound Physical constant
Chloracetic acid [N-~3,6-dioxaoctyl)- 20 0
2-methylanilide] nD = 1.51 8
Chloracetic acid [N-(3,6-dioxa- 20
heptyl)-anilide] nD = 1.5260
Chloracetic acid [2,6-diethyl~N- 20 _ 4
(3,6-dioxaheptyl)-anilide] nD - 1.521
Chloracetic acid [N-(3,6-dioxa- 20 _ 2 2
heptyl)-2-methylanilide] nD - 1-5 1
Chloracetic acid [N-(3,6-dioxa- n20 - 1 5200
octyl)-2,6-dimethylanilide] D
Chloracetic acid 12,6-diethyl~N- 20 - 1 5176
(3,6-dioxaoctyl)-anilide~ D
ChIoracetic acid ~2-chloro-N- 20 - 1 5252
(3,6-dioxaoctyl)-6-methylanilide] D
Chloracetic acid [2-chloro-N- 20 - 1 5315
(3,6-dioxaheptyl)-6-methylanilide] n
Chloracetic acid [N-(3,6-dioxa- n20 - 1 5092
octyl)-2-methylanilide] D
Chloracetic acid [2,6-dimethyl- n20 - 1 5208
N-~3,6,9-trioxadecyl)-anilide] D
Chloracetic acid l2,6-diethyl-N- n20 - 1 5190
(3,6,9-trioxadecyl)-anilide] D
Chloracetic acid I2-methyl-N- 20 ~ 1 5200
(3,6,9-trioxadecyl)-anilide] nD
Chloracetic acid [2,6-dimethyl- 20
N-(3,6,9,12-tetraoxatetradecyl)- n = 1.5104
anilide] D
Chloracetic acid [2,6-dimethyl- n20 = 1 5140
N-(3,6,9-trioxaundecyl)-anilide] D
Chloracetic acid [2-ethyl-6-methyl- n20 - I 5225
N-(3,6-dioxaheptyl)-anilide] D
Example 2
In a series of tests carried out in a greenhouse
the compounds of the present invention listed in the Table
below were each sprayed at a rate of application of 3 kg of
active substance per hectare, emulsified in 500 li~res of water
: ~ _g_

9~
per hectare, on Dig _aria s. and Echinochloa c.g. as test
plants by the pre-emergence method. Three weeks after the
treatment the results thereo~ were evaluated and the results
expressed by a numerical scale extending from 0 to 4, the value 0
representing no action and the val~le 4 representing destructlon
of the plant. As can be seen from the Table destruction of the
test plants was achieved.
Compound of the invention Digitaria Echinochloa
sangllln curs
alis ~_lli
1 0 _
Chloracetic acid ~N-(3,6-dioxa~
heptyl)-2,6-dimethylanilide] 4 4 -
Chloracetic acid [2,6-diethyl-
N-(3,6-dioxaheptyl)-anilide] 4 4
Chloracetic acid [N-(3,6
dioxaheptyl)-2-methylanilide] 4 4
Chloracetic acid ~N-(3,6-dioxa-
octyl)-2,6-dimethylanilide~ 4 4
Chloracetic acid [2,6-dimethyl
N-(3,6-dioxaoctyl)-anilide] 4 4
Chloracetic acid ~2-chloro-N-
(3,6-dioxaoctyl)-6-methylanillde] 4 4
Chloracetic acid l2-chloro-N-
(3,6-dioxaheptyl)-6-methyl-
anilide] 4 4
Chloracetic acid IN-(3,6-
dioxaoctyl)-2-methylanilide] 4 4
Chloracetic acid [2,6~dimethyl-
N-(3,6,9-trioxadecyl)-anilide] 4 4
Chloracetic acid [2,6-diethyl-
N-(3,6,9-trioxadecyl~-anilide] 4 4
Chloracetic acid ~2-methyl-N-
(3,6,9-trioxadecyl)-anilide] 4 4
Chloracetic acid ~2,6-dimethyl~
N-(3,6,9,12-tetraoxatetradecyl)-
anilide] 4 4
Chloracetic acid [2,6-dimethyl-
N-(3,6,9-trioxa~ndecyl)-
anilide] 4 4
Chloracetic acid [2-ethyl-6- ~ -
methyl-N-(3,6-dioxaheptyl)-
anilide] 4 4
--10--

g96
~ntreated o o
Example 3
___
In a series of tests carried out in a greenhouse
two different types of soil were treated after sowing the
plants listed in the heading of the Table below and before
emergence thereof with the agents being tested at a rate of
application of 1 kg of active substance per hectare. For this -~
purpose the agents were in each case uniformly sprayed over the
plants in the form of an aqueous emulsion using 500 litres of
water per hectare. In this manner it was shown three weeks
after the treatment that the action of the compound of the -
present invention, coupled with a minimal dependence on the
soil, surprisingly exhibited a high selectivity and was an
excellent herbicidal action against the weeds. The agent
used for comparison exhiblted a comparatively much weaker
action which, furthermore, was strongly dependent upon the type
of soil. The results are expressed by a numerical scale
e~tending from 0 to 10; the value 0 representing destruction
of the plant and the value 10 representing no damage. ~ ;
--11--
,. . . ,: . .

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