Note: Descriptions are shown in the official language in which they were submitted.
~o47S34
The present invention provides N-substituted halo-
ac~etanilides, a process for their manufacture, also plant
regulating agents which contain these new _ompounds as
active substances, as well as a method of selectively
S controlling weeds in crops of cultivated plants, which
comprises the use of the new active substances or of agents
which contain them.
Reference is made to the following patent speci-
fication as representing the prior art in respect of plant
regulating haloacetanilides: French patents 1.337.529,
1.419.116 and 2.028.991, Belgian patent 746.288, and
US patents 2.863.752, 3.442.945, and 3.547.620.
It is the task of this invention to provide halo-
acetanilides with improved plant regulating properties,
lS i.e. which in low rates of application control a larger
number of weed species, and, above all, highly resistant
weeds, distinctly better than the known haloacetanilides,
but without having any adverse effect on the cultures of
crop plants in which they are to be used.
Compared with the compounds known up till now, the
new N-substituted haloacetanilides according to the invention
differ fundamentally in their chemical structure to-improve
their activity. They have the formula I
'' ~
10~7534
1, `
3 ~ N \ A-0~
R4 C0-CH2X
R2
wherein R represents an alkyl radical with at most 3 carbon
atoms, an alkenyl radical with 3 or 4 carbon atoms, a cyclo-
propyl radical or a cyclopropylmethyl radical, A represents
an unsubstituted ethylene chain (-CH2-CH2) or an ethylene
chain which is monosubstituted by ethyl or mono- or disub-
stituted by methyl, Rl represents hydrogen or an alkyl
radical with at most 4 carbon atoms, R2 represents an alkyl
radical with at most 4 carbon atoms, R3 and R4 each inde-
pendently represents a substituent which is in meta-position
to the amino group, namely halogen, cyano, alkyl, alkylthio
or alkoxy, each with at most 3 carbon atoms, haloalkyl with
1 or 2 carbon atoms and 1 to 3 halogen atoms,alkoxyalkyl or
alkylthioalkyl with 2 to 4 carbon atoms, and one of the
1~ substituents R3 or R4 also represents hydrogen, and X repres-
ents chlorine or bromine.
By substituents which represent or contain an alkyl
function are to be understood - depending on the limitation
according to the definition - the lower members methyl, ethyl,
propyl, isopropyl, butyl, sec. butyl, isobutyl or tert. butyl.
-- 3 --
10~7534
By alkenyl radicals are meant the allyl group,
the various methylallyl groups, and the but-3-enyl group.
The term "halogen" comprises fluorine, chlorine,
bromine or iodine. Haloalkyl according to definition is to
be understood as meaning the mono- to trihalogenated methyl
or ethyl group~ e.g. trichloromethyl, dichloromethyl, 1,2-
dichloroethyl or trifluoromethyl.
Preferred active substances are compounds in which
X represents chlorine. Of these compounds, those whose
substituents Rl and R2 represent alkyl radicals have in the
majority of cases a particularly favourable activity spect-
rum in crop plants and weeds. Advantageously, the total
number of carbon atoms of both alkyl radicals Rl and R2
doés not exceed S.
A biologically interesting group of compounds is
that in which A, R, Rl, R2, and X have the meanings given
for the formula I, and in which one of the substituents
R3 or R4 which is in meta-position to the amino group
represents chlorine, the cyano, trifluoromethyl, methoxy,
or methylthio group, and the other represents hydrogen.
Preeminent among these compounds are those in which
A represents an ethylene chain which is monosubstituted
by methyl or ethyl.
Another biologically interesting and, for specific
fie~ds of use, preferred group of compounds of the formula I
1047534
is that in which A and R have the indicated meanings, X
represents chlorine, Rl represents a methyl group, R2
represents hydrogen, methyl, or ethyl, and wherein further
the substituent R3 in meta-position to the amino group
S represents an alkyl radical with at most 3 carbon atoms,
and R4 represents hydrogen.
Particularly preferred compounds of this last named
group are those of the formula Ia
R
C ~ H3 f H ~ CH2 ~ - R'
~ ~ 0 - CH2Cl (Ia)
wherein R2 represents hydrogen, a methyl or ethyl group,
~nd R' and R5 each independently represents a methyl or an
ethyl group.
Examples of such herbicides of the formula Ia with
particularly favourable selectivity between cultures of
crop plants and weeds are
2,3-dimethyl-N-(l'-methoxyprop-2'-yl)-N-chloroacetanilide
2,3-dimethyl-N-(l'-methoxybut-2-yl)-N-chloroacetanilide
2,3-dimethyl-6-ethyl-N-(l'-methoxyprop-2'-yl)-N-chloroacetani-
lide
2,3-dimethyl-6-ethyl-N-(l'-methoxybut-2'-yl)-N-chloroacetanilide
-- 5 --
1047534
also the compourlds of the formula I
2,6-dimethyl-3-chloro-N-(2'-methoxyethyl)-N-chloroacetanilide,
2,6-dimethyl-3-chloro-N-(l'-methoxyprop-2'-yl)-N-chloroacet-
anilide,
2,6-dimethyl-3-methoxy-N-(2'-methoxyethyl)-N-chloroacetanilide,
2,6-dimethyl-3-methoxy-N-(l'-methoxyprop-2'-yl)-N-chloroacet-
anilide,
2,6-dimethyl-3-trifluoromethyl-N-(2'-methoxyethyl)-N-chloro-
acetanilide,
2,6-dimethyl-3-trifluoromethyl-N-(l'-methoxyprop-2'-yl)-N-
chloroacetanilide.
There are a number of different ways of manufacturing
compounds of the formula I, conditioned by the possibility
of altering the sequence of different reaction steps. This
applies above all to substitution reactions in the phenyl
nucleus of the basic aniline. However, the substituents Rl
to R4 will have been introduced with advantage first before
the reactions at the amino group are effected.
The new haloacetanilides of the formula I are
manufactured according to the invention by reacting a N-
substîtuted aniline of the formula II
R
R3 ~ NH-A-OR (Il)
R4 ~
-- 6 --
104'7534
with a haloacetylating agent, preferably an anhydride or
halide of chloroacetic or bromoacetic acid. In formula II,
the symbols R, Rl to R4 and A have the same meanings as
given under formula I.
It is also possible to manufacture the compounds
of the formula I in such a way that an aniline which is
substituted by Rl to R4 is reacted optionally with
(i) 2-haloethanol or ethyl~ne oxide to introduce the hydroxy-
alkyl chain -CH2-CH2-OH, or
(ii) 2-halopropanol to introduce the hydroxyalkyl chain
CH3
-CH-CH2-OH, or
(iii) l-halopropan-2-ol or propylene oxide to introduce the
~F13
hydroxyalkyl chain -CH2- H-OH, or
(iv) 3-halobutan-2-ol to introduce the hydroxyalkyl chain
CH3lH3
-lH-CH-OH, or
(v) l-halobutan-2-ol to introduce the hydroxyalkyl chain
~ 2H5
-CH2- H- OH, or
(vi) a corresponding haloalkanol to introduce one of the
- 7
1~47534
further possible structural chains -A-OH, in which "halogen"
represents chlorine or bromine;then the resulting compound
of the formula II~
1 1 .
R3 ~ NH-A-OH (II a)
4 ~
is chloroacetylated or bromoacetylated, preferably with an
anhydride or halide of chloroacetic or bromoacetic acid, and,
finally,the still free OH group is etherified in acid medium
(e.g. HCl, H2S04) under mild conditions and in conventional
manner with an alcohol R3-OH, in which the radical R3 cor-
responds to the definition given under formula I.
The reactions can be carried out in the presence or
absence of solvents or diluents which are inert towards the
reactants. Examples of suitable solvents or diluents are:
aliphatic, aromatic or halogenated hydrocarbons, such as
benzene, toluene, xylene, petroleum ether, chlo~oben~ene, me-
~hylene chloride, ethylene chloride, chloroform; ethers and
ethereal compounds, such as dialkyl ethers, dioxan, tetrahydro-
furan; nitriles, such as acetonitrile; N,N-dialkylated amides,
such as dimethyl formamide; also dimethyl sulphoxide, and also
mixtures of these solvents.
~0~7534
As s~ able haloacetylating agents there are pre-
ferably used haloacetic anhydrides, such as chloroacetic
anhydride, and haloacetic halides, such as chloroacetyl
chloride. However, it is also possible to carry out the
reaction with haloacetic acids, their esters or amides.
The reaction temperatures are between 0 and 200C, pre-
ferably between 20 and 100C. Often, especially if halo-
acetyl halides are used, the haloacetylation is carried
oùt in the presence of an acid acceptor. Suitable acid
acceptors are: tertiary amines, such as trialkylamines,
e,g. triethylamine, pyridine and pyridine bases, or in-
organic bases, such as the oxides and hydroxides, hydrogen
carbonates and carbonates or alkali and alkaline earth
metals. Furthermore, it is also possible to use the cor-
responding aniline of the formula II as acid acceptor, in
which case a surplus must be used.
A number of starting materials of the formula II
and corresponding hydroxyalkyl derivatives (R=H) are known,
e.g. from US patent 2.381.071, 2.759.943 as well as from
Am.Soc. 84, 743 and Bull. Soc. Chim. France 1962, 303 and
1965, 2037. These starting materials, as well as those not
yet described in the literature, which fall under the
general formula II, can be manufactured easily by one of
the following known methods, for example:
'7534
a) by condensation of the aniline of the formula III which
is appropriately substituted by Rl to R4
R3
~ ~ NH2 (III)
R4 ~
with a carbonyl compound of the formula IV
IR6
0 = C - C - O - R IV
R7
in which the substituents R5, R6, and R7 represent h~gen,methyl
or ethyl, but together possess at most 2 carbon atoms, and
R has the meaning given for the formula I, and simultaneous
or subsequent catalytic hydrogenation of the resulting
azomethine of the formula V
R3 ~ R5 R6 . (V)
R4 I R7
R2
b) by reaction of the aniline of the formula III which is
appropriately substituted by Rl to R4 with a compound of
- the formula VI
- 10 -
~.n47534
Y - A - OR (VI)
wherein A and R are defined as under formula I and Y repre-
sents a halogen atom or another acid radical, in particular
an alkylsulphonic acid radical or an arylsulphonic acid
radical. Compounds of the formula VI with benzenesulphonic
acid radica~ Y are described e.g. in Can. J. Chem. 33,
1207, and those with tosyloxy radicals (CH3-C6H4-S03-) in
British patent 869,083.
There are, of course, a number of other processes
~0 for the manufacture of the starting materials of the formula
II from appropriately substituted anilines.
Some alkylsubstituted anilines of the formula III
can be manufactured from natural raw materials, e.g. coal tar
oil, others can be manufactured by known methods of which a
number are cited hereinbelow:
a) 2-alkylanilines or 2,6-dialkylanilines with C2-C4 alkyl
groups in the ortho-position of the phenyl nucleus are
advantageously manufactured from the corresponding aniline
with a C2-C4 alkene (e.g. ethylene, propylene, l-butene,
2-butene etc,) under pressure in the presence of aluminium
at temperatures above 200C lAngew. Chemie 69, 125 (1957)~.
It is thus possible e.g. to obtain 2,3-dimethyl-6-ethyl
aniline from 2,3-dimethyl aniline and ethylene, and 2,3-
dimethyl-6-isopropyl aniline from 2,3-dimethyl aniline and
propylene.
- 11 -
10~7S34
b) Starting from the appropriate toluene, ethylbenzene,
isopropyl benzene, xylene etc., there are obtained by di-
nitration and partial reduction metanitroanilines from
which, by diazotiation via the diazonium salts, meta-
nitrohalobenzenes, meta-nitrocyanobenzenes etc. are obtained,
which can then be converted by reduction into corresponding
anilines of the formula III (J. Chem. Soc. 1927, 1106).
c) Meta-alkoxyanilines are advantageously manufactured by
alkylation of the hydroxyl group of a meta-nitrophenol
IJ. Org. Chem. 26, 4749 (1962)] and subsequent reduction
of the nitro group.
d) Meta-alkylthioanilines of the formula III are obtained
appropriately by sulphochlorination of e.g. acylated aniline,
reduction of the sulphonyl chloride group to the mercapto
group and alkylation thereof (British patent 1.027.060).
e) Meta-trifluoromethyl anilines of the formula III are
obtained e.g. from 2, (4)-(di)alkyl-3,5-dinitro-benzoic acid,
partial reduction of the nitro group in 5-position to the
amino group, diazotiation ar.d elimination thereof and
subsequent conversion of the carboxyl group to the tri-
fluoromethyl group, whereupon the remaining nitro group is
reduced to the amino group (British patent 1.027.030).
A number of intermediate products which are of
importance for this invention are cited hereinbelow:
- 12 -
~04'7534
2,5-dimethyl-6~ethylaniline, b.p. 70-76C (0.7 Torr)
2,3-dimethyl-6-ethylaniline, b.p. 70-76C (0.7 Torr)
2,6-dimethyl-3-bromo-(2'-ethoxyethyl)-aniline b.p. 113-118C
(0.5 Torr)
2,3,5,6-tetramethyl-(2'-methoxyethyl)-aniline, b.p. 81-92C
(0.001 Torr)
52,3-dimethyl-(2'-methoxyethyl)-aniline, b.p. 73C (0.02 Torr)
2,3-dimethyl-(1'-methoxyprop-2'-yl)-aniline, b.p. 67-76C
(0.001 Torr)
2,3-dimethyl-(2'-ethoxyethyl)-aniline, b.p. 82-86C (0.01 Torr)
2,3,5-trimethyl-(2'-methoxyethyl)-aniline, b.p. 92C (0.3 Torr)
2,3,5-trimethyl-(1'-methoxyprop-2'-yl)-aniline, b.p. 94C
(0.5 Torr)
102,5-dimethyl-6-ethyl-(2'-methoxyethyl)-aniline, b.p. 95C
(0.7 Torr)
2,5-dimethyl-6-ethyl-(2'-ethoxyethyl)-aniline, b.p. 90C
(0.4 Torr)
2,5-dimethyl-6-ethyl-(2'-n-propoxyethyl)-aniline, b.p. 98-105C
(0.4 Torr)
2,5-dimethyl-6-ethyl-(2'-isopropoxyethyl)-aniline, b.p.
103-105C (0.6 Torr)
2,5-dimethyl-6-ethyl-(2'-allyloxyethyl)-aniline, b.p. 93C
(0.1 Torr)
152,3-dimethyl-6-ethyl-(2'-methoxyethyl)-aniline, b.p. 95C
(0.7 Torr)
2 9 3-dimethyl-6-ethyl-(2'-ethoxyethyl)-aniline, b.p. 90C
(0.4 Torr)
2,3-dimethyl-6-ethyl-(2'-n-propoxyethyl)-aniline, b.p. 98-105C
(0.4 Torr)
2,3-dimethyl-6-ethyl-(2'-isopropoxyethyl)-aniline, b.p.
103-105C (0.6 Torr)
- 13 -
1()~l'7534
2,3-dimethyl-6-ethyl-(1'-methoxyprop-2'-yl)-aniline,
b.p. 90-94C (0.8 Torr)
2,3-dimethyl-6-ethyl-(l'-metho2yprop-2'-yl)-aniline,
b.p. 102-106C (0.6 Torr)
The following Examples illustrate the process
according to the invention, including the manufacture of
starting materials. Further haloacetanilides of the formula
I, which were manufactured by one of the described processes,
are listed in the subsequent Table~
- 14 -
~047534
Example 1
a) A solution of 55.7 g (0.278 mole) of 3-bromo-2,6-dimethyl
aniline and 34.0 g (0.139 mole) of p-toluenesulphonic acis-
(2-ethoxyethyl)-ester in 100 ml of toluene is refluxed for
25 hours. After the reaction mixture has cooled J it is made
alkaline, diluted with ether, and the organic phase is washed
repeatedly with water. The dried solution is evaporated and
vacuum distillation of the residue yields the desired pro-
duct, N-(2'-ethoxy-ethyl)-3-bromo-2,6-dimethyl aniline,
b.p. 113-118C /O.STorr.
b) A suspension of lS.0 g (O.SS mole) of N-(2'-ethoxyethyl)-
3-bromo-2,6-dimethyl aniline and 5.84 g (0.055 mole) of
sodium carbonate in 60 ml of absolute ether is treated
dropwise with a solution of 6.22 g (O.SS mole) of chloro-
acetyl chloride in 30 ml of absolute ether and stirring
is æubsequently continued for 3 hours at 30C. The reaction
mixture is processed by being washed repeatedly with water,
dried and evaporated in vacuo, to give the pure product,
2,6-dimethyl-3-bromo-N-(2'-ethoxyethyl)-N-chloroacetanilide
in quantitative yield; nD = 1.5554 [compound 1~.
Br CH
CH2-CH2-0-C2H5
CO-CH2C1
- 15 -
:104'7S34
Example 2
a) A solution of 847 g (7 moles) of 2,3-dimethyl aniline
an~d 855 g (3.S moles) of p-toluenesulphonic acid -(1'-
methoxyprGp-2'-yl)-ester are refluxed for 25 hours in
3.8 litres of toluene. After the reaction mixture has cooled,
it is made alkaline and the organic phase is washed repea-
tedly with water. The dried solution is evaporated and
vacuum distillation of the residue yields 69% (of theory)
of 2,3-dimethyl-(1'-methoxyprop-2'-yl)-aniline, b.p. 67-76C/
0.001 Torr.
Instead of using p-toluenesulphonic acid ester, it is
possible to condense methoxy acetone with 2,3-dimethyl
aniline and to hydrogenate the resulting azomethine in
absolute ethanol at normal pressure in the presence of
palladium charcoal.
b) 15,5 g (0.08 mole) of the intermediate product obtained
in a) in 100 ml of absolute ether are treated with 8.5 g
(o.08 mole) of sodium carbonate. A solution of 9.1 g
(0.08 mole) of chloroacetyl chloride in 30 ml of absolute
ether is added dropwise to this suspension, whereupon the
mixture is subsequently stirred for a further 2 hours at
room temperature. The organic phase is then washed 3 times
with 50 ml of water on each occassion. The ethereal solution
is dried and the ether removed to yield as residue 14.3 g
(=69% of theory) of 2,3-dimethyl-N-(l'-methoxyprop-2'-yl)-
- 16 -
~047534
N-chloroacetanilide, m,p. 45-53~ (compound 33).
2) 2,6-dimethyl-3-bromo-N-(2'-methoxyethyl)-N-chloroacetan-
ilide,
3) 2,6-dimethyl-3-bromo-N-(2'-propoxyethyl)-N-chloroacetan-
ilide,
4) 2,6-dimethyl-3-bromo-N-(2'-isopropoxyethyl)-N- chloro-
acetanilide,
5) 2,6-dimethyl-3-bromo-N-(2'-cyclopropoxyethyl)-N-chloro-
acetanilide,
6) 2,6-dimethyl-3-bromo-N-(2'-methoxypropyl)-N-chloroacetan-
ilide,
7) 2,6-dimethyl-3-bromo-N-(2'-methoxypropyl)-N-chloroacetan-
ilide,
8) 2,6-dimethyl-3-bromo-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide,
9) 2,6-dimethyl-3-bromo-N-(l'-ethoxyprop-2'yl)-N-chloro-
acetanilide,
0) 2,6-dimethyl-3-bromo-N-(3'-methoxybut-2'-yl)-N-chloro-
acetanilide,
1) 2,6-dimethyl-3-bromo-N-(2'-allyloxyethyl)-N-chloro-
acetanilide,
2) 2,6-dimethyl-3-bromo-N-(2'-methallyloxyethyl)-N-chloro-
acetanilide,
3) 2,6-dimethyl-3-bromo-N-(2'-cyclopropylmethoxyethyl)-N-
chloroacetanilide,
4) 2,6-dimethyl-3-bromo-N-(2'-methoxyethyl)-N-bromoacetan-
ilide,
5) 2,3,6-trimethyl-N-(2'-methoxyethyl)-N-chloroacetanilide,
6) 2,3,6-trimethyl-N-(2'-ethoxyethyl)-N-chloroacetanilide,
7) 2,3,6-trimethyl-N-(2'-isopropoxyethyl)-N-chloroacetan-
ilide,
8) 2,3,6-trimethyl-N-(2'-methoxypropyl)-N-chloroacetanilide,
- 17 -
~Q47S34
19) 2,3,6-trimethyl-N-~l'-methoxyprop-2t-yl) N-chloroacetan-
ilide,
20) 2,3,6-trimethyl-N-(2'-cyclopropoxyethyl)-N-chloroacetan-
ilide,
21) 2,3,6-trimethyl-N-(2'-methoxyethyl)-N-bromoacetanilide,
22) 2,3,5,6-tetramethyl-N-(2'-methoxyethyl)-N-chloroacetan-
ilide, m.p. ~3C
23) 2,3,5,6-tetramethyl-N-(2'-ethoxyethyl)-N-chloroacetanilide,
24) 2,3,5,6-tetramethyl-N-(2'-propoxyethyl)-N-chloroacetan-
ilide,
- 25) 2,3,5,6-tetramethyl-N-(2'-isopropoxyethyl)-N-chloro-
acetanilide,
26) 2,3,5,6-tetramethyl-N-(2'-methoxypropyl)-N-chloroacetan-
ilide,
27) 2,3,5,6-tetramethyl-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide,
28) 2,3,5,6-tetramethyl-N-~l'-ethoxyprop-2'-yl)-N-chloro-
acetanilide,
29) 2,3-dimethyl-N-(2'-methoxyethyl)-N-chloroacetanilide,
nD = 1,5351,
30) 2,3-dimethyl-N-(2'-ethoxyethyl)-N-chloroacetanilide,
n20 = 1.5223,
31) 2,3-dimethyl-N-(2'-isopropoxyethyl)-N-chloroacetanilide,
32) 2,3-dimethyl-N-(2'-methoxypropyl)-N-chloroacetanilide,
33) 2,3-dimethyl-N-(l'-methoxyprop-2'-yl)-N-chloroacetanilide,
- m.p. 45-53
34) 2,3-dimethyl-N-(2'-cyclopropoxyethyl)-N-chloroacetanilide,
35) 2,3-dimethyl-N-(2'-allyloxyethyl)-N-chloroacetanilide,
36) 2,3-dimethyl-N-(2'-methoxyethyl)-N-bromoacetanilide,
37) 2,5-dimethyl-N-(2'-methoxyethyl)-N-chloroacetanilide,
. - 18 -
~04'7534
38) 2,5-dimethyl-N-(2'-ethoxyethyl)-~-chloroacetanilide,
39) 2,5-dimethyl-N-(2'-ethoxypropyl)-N-chloroacetanilide,
40) 2,6-dimethyl-3-chloro-N-(2'-ethoxyethyl)-N-chloroacetan-
ilide,
41) 2,6-dimethyl-3-chloro-N-(2'-methoxyethyl)-N-chloroacetan-
ilide, m.p. 52-55
42) 2,6-dimethyl-3-chloro-N-(2'-propoxyethyl)-N~chloroacetan-
ilide,
43) 2,6-dimethyl-3-chloro-N-(2'-isopropoxyethyl)-N-chloro-
acetanilide,
44) 2,6-dimethyl-3-chloro-N-(2'-cyclopropoxyethyl)-N-chloro-
acetanilide,
45) 2,6-dimethyl-3-chloro-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
46) 2,6-dimethyl-3-chloro-N-(2'-ethoxypropyl)-N-chloro-
acetanilide,
47) 2,6-dimethyl-3-chloro-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide m,p. 54-56,
48) 2,6-dimethyl-3-chloro-N-(l'-ethoxyprop-2'-yl)-N-chloro-
acetanilide,
49) 2,6-dimethyl-3-chloro-N-(3'-methoxybut-2'-yl)-N-chloro-
acetanilide,
50) 2,6-dimethyl-3-chloro-N-(2'-allyloxyèthyl)-N-chloro-
acetanilide,
51) 2,6-dimethyl-3-chloro-N-~2'-methallyloxyethyl)-N-chloro-
acetanilide,
52) 2,6-dimethyl-3-chloro-N-(2'-cyclopropylmethoxyethyl)-N-
chloroacetanilide,
53) 2,6-dimethyl-3-chloro-N-(2'-methoxyethyl)-N-bromoacetan-
ilide,
54) 2-methyl-3-bromo-6-ethyl-N-(2'-ethoxyethyl)-N-chloro-
acetanilide,
- 19 -
\
~047S34
55) 2-methyl-3-~romo-6-ethyl-N-(2'-methoxyethyl)-N-chloro-
acetanilide,
56)1 2-methyl-3-bromo-6-ethyl-N-(2'-propoxyethyl)-N-chloro-
acetanilide,
57 2-methyl-3-bromo-6-ethyl-N-(2'-isopropoxyethyl)-N-chloro-
acetanilide,
58) 2-methyl-3-bromo-6-ethyl-N-(2'-cyclopropoxyethyl)-N-
chloroacetanilide,
59) 2-methyl-3-bromo-6-ethyl-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
60) 2-methyl-3-bromo-6-ethyl-N-(2'-ethoxypropyl)-N-chloro-
scetanilide,
61) 2-methyl-3-bromo-6-ethyl-N-(l'-methoxyprop-2'-yl)-N-
chloroacetanilide,
62) 2-methyl-3-bromo-6-ethyl-N-(l'-ethoxyprop-2'-yl)-N-
chloroacetanilide,
63) 2-methyl-3-bromo-6-ethyl-N-(3'-methoxybut-2'-yl)-N-
chloroacetanilide,
64) 2-methyl-3-bromo-6-ethyl-N-(2'-allyloxyethyl)-N-chloro-
acetanilide,
65~ 2-methyl-3-bromo-ethyl-N-(2'-methallyloxyethyl)-N-
chloroacetanilide,
66) 2-methyl-3-bromo-6-ethyl-N-(2'-cyclopropylmethoxyethyl)-
N-chloroacetanilide,
67) 2-methyl-3-bromo-6-ethyl-N-(2'-methoxyethyl)-N-bromo-
acetanilide,
68) 2,6-dimethyl-3-methoxy-N-(2'-methoxyethyl)-N-chloro-
acetanilide, m.p. 54-56,
69) 2,6-dimethyl-3-methoxy-N-(2'-ethoxyethyl)-N-chloro-
acetanilide,
70) 2,6-dimethyl-3-methoxy-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
71) 2,6-dimethyl-3-methylthio-N-(2'-methoxyethyl)-N-chloro-
acetanilide, m.p. 51-53,
- 20 -
10~7534
72) 2,6-dimethyl-3-methylthio-N-(2'-ethoxyethyl)-N-chloro-
acetanilide,
73) 2,6-dimethyl-3-methylthio-N-(l'-methoxyprop-2'-yl)-N-
chloroace~anilide, m.p. 49-52,
7~ 2,6-dimethyl-3-cyano-N-(2'-methoxyethyl)-N-chloro--
acetanilide, m.p. 53-56,
75) 2,6-dimethyl-3-cyano-N-(2'-ethoxyethyl)-N-chloro-
acetanilide,
76) 2,6-dimethyl-3-cyano-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
77) 2,6-dimethyl-3-cyano-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide, m.p. 55-58C,
78) 2,6-dimethyl-3-trilfuoromethyl-N-(2'-methoxyethyl)-N-
chloroacetanilide, m.p. 55-57C,
79) 2,6-dimethyl-3-trifluoromethyl-N-(2'-ethoxyethyl)-N-
chloroacetanilide,
80) 2,6-dimethyl-3-methoxymethyl-N-(2'-methoxyethyl)-N-
chloroacetanilide,
81) 2,6-dimethyl-3-methoxymethyl-N-(2'-ethoxyethyl)-N-
chloroacetanilide,
82) 2,6-diethyl-3-bromo-N-(2'-ethoxyethyl)-N-chloroacetan-
ilide,
83) 2,6-diethyl-3-bromo-N-(2'-methoxyethyl)-N-chloroacetan-
ilide,
84) 2,6-diethyl-3-bromo-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide,
85) 2,3-dimethyl-6-isopropyl-N-(2'-methoxyethyl~-N-chloro-
acetanilide,
86) 2,3-dimethyl-6-isopropyl-N-(2'-ethoxyethyl)-N-chloro-
- acetanilide,
- 87) 2,3-dimethyl-6-isopropyl-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
- 21 -
~04'~534
88) 2,3-dimethyl-6-isopropyl-N-(l'-methoxyprop-2'-yl)-N-
chloroacetanilide,
89) 2,3-dimethyl-6-isopropyl-N-(2'-methoxyethyl)-N-bromo-
acetanilide,
90) 2,5-dimethyl-6-ethyl-N-(2'-methoxyethyl)-N-chloroacetan-
ilide,nD = 1.5335,
91) 2,5-dimethyl-6-ethyl-N-(2'-ethoxyethyl)-N-chloroacetan-
ilide, nD = 1.5282,
92) 2,5-dimethyl-6-ethyl-N-(2'-isopropoxyethyl)-N-chloro-
acetanilide, n20 = 1.5231,
93) 2,5-dimethyl-6-ethyl-N-(l'-methoxybut-2'-yl)-N-chloro-
acetanilide,
94) 2,5-dimethyl-6-ethyl-N-(2'-methoxypropyl)-N-chloro-
acetanilide,
95) 2,5-dimethyl-6-ethyl-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide,
96) 2,5-dimethyl-6-ethyl-N-(l'-ethoxyprop-2'-yl)-N-chloro-
acetanilide,
97) 2,5-dimethyl-6-ethyl-N-(2'-cyclopropoxyethyl)-N-chloro-
acetanilide,
98) 2,5-dimethyl-6-ethyl-N-(2'-propoxyethyl)-N-chloroacetan-
ilide, nD = 1.5252,
99) 2,5-dimethyl-6-ethyl-N-(2'-allyloxyethyl)-N-chloroacetan-
ilide, nD = 1.5357,
00) 2,6-dimethyl-3-methoxy-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide, m.p. 55-57C,
101) 2,6-dimethyl-3-trilfuoromethyl-N-(l'-methoxyprop-2'-yl)-
N-chloroacetanilide, m.p. 55-59C,
102) 2,5-dimethyl-N-(2'-methoxyethyl)-N-chloroacetanilide,
m.p. 42-45C,
103) 2,5-dimethyl-N-(2'-ethoxyethyl)-N-chloroacetanilide,
~DO= 1.5287,
- 22 -
~047534
10~) 2,5-dimethyl-N-(2'-propoxyethyl)-N-chloroacetanilide,
n2 = 1.5219,
O'j) 2,5-dimethyl-N-(2'-isopropoxyethyl)-N-chloroacetanilide,
b.p. 115-120C/0.001 Torr,
06) 2,5-dimethyl-N-(2'-methoxypropyl)-N-chloroacetanilide,
nD = 1.5325,
07) 2,5-dimethyl-N-(l'-methoxyprop-2'-yl)-N-chloroacetan-
ilide, m.p. 44-46C,
08) 2,5-dimethyl-N-(l'-ethoxyprop-2'-yl)-N-chloroacetan-
ilide, n20 = 1.5234,
09) 2,5-dimethyl-N-(2'-cyclopropoxyethyl)-N-chloroacetanilide,
b.p. 118-123C/0.001 Torr,
10) 2,3-dimethyl-6-ethyl-N-(2'-methoxyethyl)-N-chloroacetan-
ilide, nD = 1.5335,
11) 2,3-dimethyl-6-ethyl-N-(2'-ethoxyethyl)-N-chloroacetan-
ilide, nD = 1.5282,
12) 2,3-dimethyl-6-ethyl-N-(2'-propoxyethyl)-N-chloroacetan~
ilide, nD = 1.5252,
13) 2,3-dimethyl-6-ethyl-N-(2'-isopropoxyethyl)-N-chloroacet-
anilide, nD = 1.5231,
14) 2,3-dimethyl-6-ethyl-N-(2'-methoxypropyl)-N-chloroacetan-
ilide, nD = 1.5296,
15) 2,3-dimethyl-6-ethyl-N-(l'-methoxyprop-2'-yl)-N-chloroacet-
anilide, nD = 1.5294,
16) 2,3-dimethyl-6-ethyl-N-(l'-ethoxyprop-2'-yl)-N-chloroacet-
anilide, n20 = 1.5217,
17) 2,3-dimethyl-6-ethyl-N-(2'-cyclopropoxyethyl)-N-chloro-
acetanilide,
18) 2,3-dimethyl-6-ethyl-N-(l'-propoxyprop-2'-yl)-N-chloro-
acetanilide,
- 23 -
~0~'753~
119) 2,3-dimethyl-6-ethyl-N-(l'-methoxybut-2'-yl)-N-chloro-
ace~anilide, b.p. 122-128C/0.001 Torr,
20) 2,3-dimethyl-6-ethyl-N-(2'-methoxybut-3'-yl)-N-chloro-
acetanilide, b.p. 138-143~C/0.002 Torr,
21) 2,3-dimethyl-6-ethyl-N-(l'-methoxy-2'-methylprop-2'-yl)-
N-chloroacetanilide b.p. 132-136C/0.001 Torr.
The active substances according to the invention
are stable compounds and possess very good herbicidal pro-
perties against annual grasses and related plants of the
genera Setaria, Digitaria, etc., against grasses such as
Lolium species and against dicotyledonous weeds such as
Amaranthus, Sesbania, Chrysanthemum, Ipomoea, Sinapis,
Galium, Pastinaca, without causing damage to the cultivated
plants in respect of which the use of the active substances
is in~ended, for example soya, alfalfa, peas, lentils,
ground nuts, cotton, maize, coffee, tea, bananas, pineapples,
sugar beet, sugar cane, potatoes, paprika, tomatoes, spinach,
onions, aubergines, sun flowers, tobacco, Brassica species
such as rape and cabbage, but also cereals, such as barley,
oats, rye, wheat, or dry rice and water rice.
The active substances are applied either before
or after the germination of the cultivated plants and of
the weeds and grasses (pre-and postemergence); preemergence
application is preferred. The rates of application are bet-
ween 0.1 and 10 kg of active substance per hectare. But
in preemergent application the weeds are virtually destroyed
- 24 -
iO47S34
using a rate of application as low as 0,25 '~g of active
substance per hectare. Normally up to 10 k~ of active
substance per hectare are used to prevent railway ambankments,
factory grounds, roads etc, from becoming overgrown with
weeds.
Furthermore, the active substances of the formula
I also exhibit growth regulating properties in that they
delay the growth in height and increase the trillering of
grasses (e.g. in existing grass plantations). Profusely
and rapidly seeding weeds are inhibited in their germina-
tion and emergence and so removed from cultivations of crop
plants. The acylated amines of the formula I also possess
defoliating properties and can be used for delaying blos-
soming. The storage capability of substances contained in
plants is improved generally by the active substances
according to the invention. For example, the sugar content
in sugar beet or the starch content or potatoes or the fat
content of soya beans or ground nuts is increased.
As already mentioned, herbicidal haloacetanilides
of comparable constitution are known from the literature.
However, these either have only alkoxymethyl groups at the
nitrogen atom (US patent 3.547.620) or in one ortho-position
of the phenyl radical carry other tertiary alkyl substituents,
such as in particular tert. butyl (French patent 1.337.529).
It is disclosed in the literature that the N-alkoxy-
- 25 -
10~'7534
me~hyl derivatives represent the best products and are
superior at all events to the corresponding N-alkoxyethyl
and N-alkoxypropyl derivatives (US patent 3.547.620, Example
85~. On the basis of this pu~lication, one skilled in the
art had to assume that N-substituted haloacetanilides with
alkoxy, alkenyloxy and cycloalkoxy groups which are bonded
to the nitrogen atom of the anilide through alkylene radi-
cals with 2 chain members, regardless of how they are sub-
stituted in the phenyl nucleus, are not suitable as herbicides
for practical purpose.
The surprising discovery has now been made that
the new active substances of the formula I according to
the invention, which do not have the supposedly most favour-
able constitution for the herbicidal activity as claimed in
US patent 3.547.620, and which furthermore are substituted
in the phenyl ring in at least one meta-position to the
amino group, are superior to these N-alkoxymethyl-2,(6)-(di)
alkyl-chloroacetanilides and other closely related compounds
described in the literature in the selective control of
weeds.
- ~6 -
~0~753
Example 3
Control of Panicum species and other mor.ocotyledonous weeds
_ various cultures of crop plants (preemergence method)
One day after the test plants have been sown in seed dishes,
dilute aqueous suspensions of the active substances are
sprayed in such concentrations on the surface of the soil as
to correspond to rates of application of 2 kg, 1 kg and 0.5 kg
per hectare. The seed dishes are kept at 22 and 25C and
about 70% relative humidity. The test is evaluated after 28
days according to the following rating:
9 = plants undamaged (as control test)
1 = plants destroyed
8-2 = intermediate stages of damage
- = not tested
Known haloacetanilides were used as comparison compounds:
Compound A: 2-methyl-N-(l'-methoxyprop-2'-yl)-N-chloro-
acetanilide (French patent 2.028.991)
Compound B: 2,6-diethyl-N-(methoxymethyl)-chloroacetanilide
(commercial product) (US patent 3.547.620).
- 27 -
~04'7534
Tablel
.
n ~-~ m~r ~ 3
O ~ P~ p7 ~ - O `~ 0 1_ ~ O O
3 ~ ~o~ ~.
~ ~ 1'- a~ ~'- p~ ~. p~ p) N
. oq ~o o O ~ g ~ ~ 0
Z 1~ ~ ~ ~ c~
o c~ p,
~ ~ P~ ~n
_ 1~............................ .
2 1111111 898968-
22 1 1111112 998988-
0.5 1112224 999999_
2 111-111 9999889
29 1 111-212 9999999
0.5 121-323 9999999
2 1111111 8898847
30 1 1111111 8999988
0,5 1112212 9999999
2 1111111 89998-7
90 1 1112111 89999_9
0,5 1113122 99999-9
2 1111111 9999899
91 1 1111121 9999999
_ 0.5 1111131 . 9999999
-28-
T bl 1 ( tio4t7~3~ 4
~ _ . .
3 ~ o I ~'s' ' 1~ 5 ~D ~" 3 ~ o p~ w'
~ o~
2 111111 - 199999 ~ 7
9~ l 111112 - 19999998 .
0.5 11 l 23 - - 19999999
2 11111 - 1 8999999 .
92 1 11121 - 2 9999999
O.S 11121 - 3 9999999
2 11111 - 1 9999899
99 1 1 i 121 - 2 9999999
. 0.5 11132 - 3 9999999
2 1111111 7989759
. 33 1 1111111 8989989
0.5 1113141 9999999
. 2 1 ~ 17123 7788438
A 1 1119244 7799569
. . 0.5 1319564 9999799
. ~ 1114 - 22 8598439
B 1 1115232 9699849
. L ~ 1217 - 44 L9799999
- 29 -
1~4753~
It is evident from the comparison results that the selecti-
vity of the compounds of the present invention in the control
of weeds and protection of crop plants is distinctly better
than that of the closest comparable known compounds. In the
rate of application of 1 kg of active substance per hectare
which is of importance for practical purpose, the comparison
compounds A and B have no satisfactory tolerance in crops
of cultivated plants, and on the other hand, important
weeds such as Alopecurus, Lolium and Rottboellia are in-
sufficiently controlled.
Example 4
Control of weeds in rice
Earthenware dishes filled with garden soil are sown on the
one hand with rice (Oryza oryzoides) and on the other hand
with weeds. The active substance solution was prepared from
a 25% wettable powder and applied to the surface of the soil
immediately after the sowing (amount of the solution: 100
ml/m ). The dishes were kept in a greenhouse at 24-27C and
70% relative humidity. Evaluation took place 28 days later
according to the rating given in Example 3.
- 30 -
Table 2
Comp. Rate of applic. Cyperus Setaria Echino- Rice
No. in kg AS/ha esculentusitalica chloa c.g.
2 1 1 1 7
98 1 1 1 1 8
0.5 1 1 1 9
2 1 1 1 8
9~ 1 1 1 1 8
0.5 1 1 1 9
Example 5
Growth inhibition in grasses ~postemergence method)
Seeds of the grasses Lolium perenne, Poa pratensis, Pestuca ovina, and
Dactylis glomerata were sown in plastic dishes filled with an earth/turf/sand
mixture. After 3 weeks the germinated grasses were cut bac~ to a height of
4 cm above the soil and 2 days later sprayed with aqueous spray broths of
active substances of the formula I. The amount of active substance corres-
ponded to a rate of application of 5 kg of active substance per hectare.
Fourteen days after application the growth of the grasses was evaluated
according to the following linear rating:
1 = strong inhibition (no growth from the time of application)
9 = no inhibition (growth as untreated control)
lV~'7534
Of the tested substances, very strong growth inhibition was
achieved with the following compounds (rating l to 3): 29,
30, 33, 37, 41, 68, 71, 73, 78, 90, 95, 100, 102, 107 and
110 .
The agents according to the invention are manufac-
tured in known manner by intimately mixing and/or grinding
active substances of the formula I with the suitable carriers,
optionally with the addition of dispersants or solvents which
are inert towards the active substances. The active substances
may take and be used in the following forms:
Solid forms:
dusts, tracking agents, granules, coated granules,
impregnated granules and homogeneous granules.
Liquid forms:
a) active substances which are dispersible in water:
wettable powders, pastes, emulsions;
b) solutions.
To manufacture solid forms ~dusts, tracking agents),
the active substances are mixed with solid carriers. Suitable
carriers are, for example: kaolin, talcum, bolus, loess,
chalk, limestone, ground limestone, attaclay, dolomite,
diatomacous earth, precipitated silica, alkaline earth
silicates, sodium and potassium aluminium silicates (feldspar
and mica), calcium and magnesium sulphates, magnesium oxide,
10~7S34
ground synthetic materials, fertilisers, for example a~monium
sulphate, ammonium phosphate, ammonium nitrate, urea, ground
vegetable products, such as corn meal, bark dust, sawdust,
nutshell meal, cellulose powder, residues of plant extrac-
tions, activated charcoal etc. These substances can either
be used singly or in admixture with one another.
The particle size of the carriers for dusts is ad-
vantageously up to 0.1 mm, for tracking agents from about
0.075 to 0.2 mm, and for granules 0.2 mm or larger.
The solid forms contain the active substances in
concentrations from 0.1% to 80%.
To these mixtures can also be added additives which
stabilize the active substance and/or non-ionic, anionic and
cationic surface active substances, which for example improve
the adhesion of the acSive ingredients on plants or parts of
plants Cadhesive and agglutinants) and/or ensure a better
wettability (wetting agents) and dispersibility (dispersing
agents). Examples of suitable adhesives are the following:
olein/chalk mixture, cellulose derivatives tmethyl cellulose,
carboxymethyl cellulose), hydroxyethyl glycol ethers of
monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide
radicals per molecule and 8 to 9 carbon atoms in the alkyl
radical, lignin sulphonic acids, their alkali metal and
alkaline earth metal salts, polyethylene glycol ethers
- 33 -
1()4';'534
~carbowaxes)*, fatty alcohol polyethylene glycol ether having
5 to 30 ethylene oxide radicals per molecule and 8 to 18
carbon atoms in the fatty alcohol moiety, condensation pro-
duct of urea and formaldehyde, and also latex products.
The water-dispersible concentrates of the active
substance i~e. wettable powders, pastes and emulsifiable
concentrates, are agents which can be diluted with water to
any concentration desired. They consist of active substance,
carrier, optionally additives which stabilize the active
substance, surface-active substances and anti-foam agents
and, optionally, solvents. The active substance concentrations
in these agents are from 5-80%.
Wettable powders and pastes are obtained by mixing
and grinding the active substances with dispersing agents
and pulverulent carriers in suitable apparatus until homo-
geneity is attained. Carriers are, for example, those mentioned
for the solid forms of application. In some cases it is advan-
tageous to use mixtures of different carriers. As dispersing
agents there can be used, for example, condensation products
of sulphonated naphthalene and sulphonated naphthalene deri-
vatives with formaldehyde, condensation products of naphthalene
or naphthalene sulphonic acids with phenol and formaldehyde,
as well as alkali, ammonium and alkaline earth metal salts of
lignin sulphonic acid, in addition, alkylaryl sulphonates,
*Trade Mark
- 34 -
~0~7534
alkali and alkaline ea~h metal ~alts of dibutyl naphthalene
sulphonic acid, fa~ty alcohol sulphates such as salts of
sulphated hexadecanols, heptadecanols, octadecanols, and
sa'Lts of sulphated fatty alcohol glycol ethers, the sodium
saLt of oleoyl ethionate, the sodium salt of oleoly methyl
tauride, ditertiary acetalene glycols, dialkyl dilauryl
ammonium chloride and fatty acid alkali and alkaline earth
salts.
Suitable anti-foam agents are silicones. The active
substances are so mixed, ground sieved and strained with the
additives mentioned above that, in wettable powders, the
solid particle size of from 0.02 to 0.04 and in pastes, of
0.03 is not exeeded.. To produce emulsifiable concentrates
and pastes, dispering agents such as those given in the
previous paragraphs, organic solvents and water are used.
Examples of suitable solvents are: alcohols, benzene, xylenes,
toluene, dimethyl sulphoxide, N.N-dialkylated amides, N-
oxides of amines, especially trialkylamines, and mineral
oil fractions boiling between 120 and 350C. The solvents
mux~ be practically odourless, not phytotoxic, inert to
the active substances and may not have too low a flash point.
Furthermore, the agents according to the invention
; can be applied in the form of solution. For this purpose
the active substance, or several active substances of general
formula I, is dissolved in suitable organic solvents, mixtures
- 35 -
~047S34
of solvents or in water. Aliphatic and aromatic hydrocarbons,
chlorinated derivatives thereof, alkyl naphthalenes and mi-
neral oils singly or in admixture, can be used as organic
solvents. The solutions contain the active substance in a con-
centration range from 1% to 20%. These solutions can either
be applied with the acid of a propellant gas (spray) or wi~h
special spray (as aerosol).
The agents described according to the invention
can be mixed with other biocidally active substances or
agents. Thus in order to broaden the activity spectrum the
new agents may contain, for example, insecticides, fungi-
cides, bactericides, fungistatics, bacteriostatics, nema-
tocides or further herbicides, in addition to the cited
active substances of the formula I. The agents according
to the invention may also contain plant fertilisers, trace
elements etc.
The active substances of the formula I can, for
example, be formulated as follows. The parts denote parts
by weight.
Granules
- The following substances are used to manufacture
5% granules:
S parts of active substance of the formula I
0.25 part of epichlorohydrin,
- 36 -
1047534
0.25 part of cetyl polyglycol ether,
3.50 parts of polyethylene glycol ether,
91 parts of kaolin (particle size: 0.3-0.8 mm).
The active substance is mixed with epichlorohydrin
anc3 the mixture dissolved in 6 parts of ace~one, then poly-
ethylene glycol ether and cetyl polyglycol ether are added.
The resulting solution is sprayed on kaolin and then evapo-
rated in vacuo.
Wettable powder
The following consituents are used to manufacture
a) a 50%, b) a 25% and c) a 10% wettable powder:
a)50 parts of active substance of the formula I,
e.g. 2,3-dimethyl-N-(l'-methoxyprop-2'-yl)-N-
chloroacetanilide,
5 parts of sodium dibutylnaphthalene sulphonate,
3 parts of naphthalenesulphonic acid/phenolsul-
phonic acid/formaldehyde condensate (3:2:1),
20 parts of kaolin,
22 parts of champagne chalk;
b)25 parts of active substance of the formula I,
5 parts of oleylmethyltaurid-sodium salt,
2,5 parts of naphthalenesulphonic acid/formaldehyde
condensate,
0.5 part of carboxymethyl cellulose,
- 37 -
7534
5 parts of neutral potassium-aluminium-silicate,
62 parts of kaolin;
c) 10 parts of N-(2'-methoxyethyl)-~,6-diethyl-chloro-
acetanilide,
3 parts of a mixture of the sodium salts of
saturated fatty alcohol sulphates,
5 parts of naphthalenesulphonic acid/formaldehyde
condensate,
' 82 parts of kaolin.
The indicated active substance is applied to the
corresponding carriers (kaolin and chalk) and then these are
mixed and ground, to yield wettable powders of excellent wet-
tability and h,aving an excellent capacity for forming sus-
pension. By diluting these wettable powders with water it
15, is possible to obtain suspensions of any desired concen-
tration,
Paste
The following substances are used to manufacture a
45% paste: .
45 parts of active substance of the formula I,
5 parts of sodium aluminium silicate,
14 parts of cetyl polyglycol ether with 8 mols of
ethylene oxide,
1 part of oleyl polyglycol ether with 5 mols of
ethylene oxide,
- - 38 -
` ~047534
2 parts of spindle oil,
10 parts of polyethylene glycol,
38-18 parts of water.
The active substance is intimately mixed with the
adclitives in appropriate devices and ground. A paste is
obtained from which, by dilution with water, is possible
to manufacture suspensions of every desired concentration
of active substance.
Emulsion Concentrate
To manufacture a 25% emulsion concentrate
25 parts of active substance of the formula I,
5 parts of a mixture of nonylphenolpolyoxy-ethoxy-
ethylene and calcium dodecylenesulphonate,
35 parts of 3,5,5-trimethyl-2-cyclohexan-1-one,
40-30 parts of dimethyl formamide,
are mixed together. this concentrate can be diluted with
water to give emulsions in desired concentrations. Such
emulsions are suitable for controlling weeds in cultures
of crop plants.
- 39 -
