Note: Descriptions are shown in the official language in which they were submitted.
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Substituted heteroarvlmethvl compounds
The invention relates to novel substituted heteroarylmethyl compounds, to
processes
for their preparation and to their use as herbicides.
Substituted arylmethyl compounds are already known from the (patent)
literature as
potential herbicides (cf. DE-A-2526358, US-A-4249934, US-A-5262390, WO-A-
9621647). However, these compounds have not attained any practical importance
worth mentioning.
The present invention accordingly provides novel substituted heteroarylmethyl
compounds of the general formula (I)
Zz X'
Xz ~ / Q (I)
in which
Q represents O, S, SO or S02,
X 1 represents hydrogen, hydroxyl, mercapto, amino, nitro, formyl, carboxyl,
cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case
optionally cyano-, halogen- or alkoxy-substituted alkyl, alkoxy, alkylthio,
alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl,
alkoxycarbonyl, alkylcarbonylamino, alkoxycarbonylamino or
alkylsulphonylamino,
X2 represents hydrogen or halogen,
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Z i represents optionally substituted heteroaryl from the series consisting of
furyl,
benzofuryl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,
benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzimidazolyl,
pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
quinazolinyl or quinoxalinyl, and
Z2 represents one of the groupings below
Q' Q' R' R'
N- R ~ N- Q ~N R, I ~N
R~ RziN~N\ NuN\
Q' Q' IQI' IQI'
R' Rz Rz R'
w
R' \ N R' NON Rz'~NiN O' RzwN~N
~ l ~ i
N
' \ ' '~ \ ' \
R R Q Q
z R'
R' O Q' I R' R' R' O'
R' N R' \
N N ~ \
N R'
Q'
Rz
R' Q' I
I~I ' ' O N Q'
z ~ R~N~ ~ R N Q
RAN Q ~ Q
N /N~\ N N\ Rz/N N\
' Rz N--
Q ~ '
O Q
where
Q l represents O or S,
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R1 represents hydrogen, cyano, halogen, or represents in each case
optionally cyano-, halogen- or alkoxy-substituted alkyl, alkoxy,
alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino,
alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkinyl, alkinyloxy,
alkinylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio or
cycloalkylamino, or optionally together with an adjacent R1 represents
alkanediyl (alkylene), and
R2 represents hydrogen, cyano, formyl, or represents in each case
optionally cyano-, halogen- or alkoxy-substituted alkyl, alkylcarbonyl,
alkoxycarbonyl, alkenyl or alkinyl.
In the definitions, the hydrocarbon chains, such as alkyl - including in
combination
1 S with heteroatoms, such as in alkoxy - are in each case straight-chain or
branched.
The invention preferably provides compounds of the formula (I) in which
Q represents O, S, SO or S02,
X1 represents hydrogen, hydroxyl, mercapto, amino, nitro, formyl, carboxyl,
cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case
optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy,
alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino,
alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkoxycarbonylamino or
alkylsulphonylamino having in each case 1 to 6 carbon atoms in the alkyl
groups,
X2 represents hydrogen or halogen,
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Z1 represents optionally substituted heteroaryl from the series consisting of
furyl,
benzofuryl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,
benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzimidazolvl.
pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
quinazolinyl or quinoxalinyl, where the possible substituents are preferably
selected from the list below:
nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl, sulpho,
chlorosulphonyl, aminosulphonyl, halogen, in each case optionally cyano-,
halogen- or C 1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio,
alkylsulphinyl,
alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl,
alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or
alkylsulphonylamino having in each case 1 to 4 carbon atoms in the alkyl
groups or phenyl,
and
ZZ represents one of the groupings below
Q~ Qi Ri R~
R~ Q~ Ri
/ vN- I \N- W N I w N
R~ Rz~N N~ N N~
Q'
R' R2 RZ '
R
w
R~ \ N R' NON RwN~N Q' RWN~N
-N
R R Q Q
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z R'
R~ O Q~ I R~ R~ R~ Q~
R~ N R~
N-N~ ~ ( / N\
N R~ ~N \
Q
R~ O~ Rz Rz
' I ' Q N Q'
z ~ Rw ~ ~ R N Q
RwN Q ; Q
N z/N~~ - N N\ Rz/N N\
R N
Q \ Q~
Q
where
Q 1 represents O or S,
R1 represents hydrogen, cyano, haloben, represents in each case
optionally cyano-, halogen- or Cl-C4-alkoxy-substituted alkyl, alkoxy,
alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino
having in each case 1 to 6 carbon atoms in the alkyl groups, represents
in each case optionally halogen-substituted alkenyl, alkenyloxy,
alkenylthio, alkenylamino, alkinyl, alkinyloxy or alkinylthio having in
each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups,
1S represents in each case optionally cyano-, halogen- or C1-C4-alkyl-
substituted cycloalkyl, cycloalkyloxy, cycloalkylthio or
cycloalkylamino having in each case 3 to 6 carbon atoms in the
cycloalkyl groups, or optionally together with an adjacent R1
represents alkanediyl (alkylene) having 3 to 5 carbon atoms, and
R2 represents hydrogen, cyano, formyl, represents in each case optionally
cyano-, halogen- or Cl-C4-alkoxy-substituted alkyl, alkylcarbonyl,
alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl
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groups, or represents in each case optionally halogen-substituted
alkenyl or alkinyl having in each case 3 to 6 carbon atoms.
The invention relates in particular to compounds of the formula (I) in which
Q represents O, S, SO or 502,
X 1 represents hydrogen, hydroxyl, mercapto, amino, nitro; formyl, carboxyl,
cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents in
each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,
methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-
propylamino, dimethylamino, diethylamino, acetyl, propionyl,
i S methoxycarbonyl, ethoxycarbonyl, acetylamino, propionylamino,
methoxycarbonylamino, ethoxycarbonylamino, methylsulphonylamino,
ethylsulphonylamino, n- or i-propylsulphonylamino,
XZ represents hydrogen, fluorine, chlorine or bromine,
Z1 represents optionally substituted heteroaryl from the series consisting of
furyl,
benzofuryl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,
benzoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzimidazolyl,
pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
quinazolinyl or quinoxalinyl, where the possible substituents are preferably
selected from the list below:
nitro, amino, hydroxyl, carboxyl, cyano, carbamoyl, thiocarbamoyl,
aminosulphonyl, fluorine, chlorine, bromine, in each case optionally cyano-,
fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-
propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or
t-
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butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,
methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,
methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,
acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-
S propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-
propylaminocarbonyl, acetylamino, propionylamino, n- or i-butyroylamino,
methoxycarbonylamino, ethoxycarbonylamino, n- or i-
propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-
propylsulphonylamino, n-, i-, s- or t-butylsulphonylamino or phenyl,
and
Z2 represents one of the groupings below
Q' Q' R, R'
\ R~ Q ~ N R~ ~ N
~N- I ~N- I I I
R~ ~ N N\ N N\
Rzi
R' RZ RZ R'
I I l
R' \ N R' NON Rz~N~IV Q~ RwN~IV
W
~ l ~ i
N
R R Q Q
R'
R~ O Q~ ( R~ R~ R~ Q~
R~ N R~ \
N-N ~ N\
N R~
Q'
Rz
R' Q' Rz
( ' Q N Q'
z , RzwN~Q, R N Q
R w N Q
N % ~~ N N\ Rz/N N\
RZ N -
Q Qi
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where
Q1 represents O or S,
R1 represents hydrogen, cyano, fluorine, chlorine, bromine, represents in
each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-
substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-
propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,
ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino,
ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
represents in each case optionally fluorine-, chlorine- or bromine-
substituted ethenyl, propenyl, propenyloxy, propenylthio,
propenylamino, ethinyl, propinyl, propinyloxy or propinylthio,
represents in each case optionally cyano-, fluorine-, chlorine-, methyl-,
ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,
cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino
or cyclohexylamino, or optionally together with an adjacent R1
represents propane-1,3-diyl (trimethylene) or butane-1,4-diyl
(tetramethylene), and
R2 represents hydrogen, cyano, formyl, represents in each case optionally
cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,
ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl,
methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or
represents in each case optionally fluorine-, chlorine- or bromine-
substituted propenyl, butenyl, propinyl or butinyl.
A very particularly preferred group are those compounds of the general formula
(I) in
which Z2 represents the heterocyclic grouping below and Q, XI, X2 and Zl and
R2
have the meanings given above as being particularly preferred.
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Rz
I
RzwNiN~O
-N
O
A further very particularly preferred group are those compounds of the general
formula (I) in which Z2 represents the heterocyclic grouping below and Q, X1,
X2
and Z1 and R1 and R2 have the meanings given above as being particularly
preferred.
Rz
R, N ~
/N
R'
Most preference is given to compounds of the formula (Ia)
Zz \ x,
Xz ~ / Q (Ia)
in which
Q, X1, X2, Z1 and ZZ have the meanings given in Table 1 (after the Preparation
Examples) and to the compounds of Preparation Examples 1 and 2.
The abovementioned general or preferred radical definitions apply both to the
end
products of the formula (I) and correspondingly to the starting materials or
intermediates required in each case for the preparation. These radical
definitions can
be combined with one another at will, i.e. including combinations between the
given
preferred ranges.
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The novel substituted heteroarylmethyl compounds of the general formula (I)
have
strong and selective herbicidal activity.
S The novel substituted heteroarylmethyl compounds of the general formula (I)
are
obtained when
(a) phthalic anhydride or 3,4,5,6-tetrahydro-phthalic anhydride is reacted
with
aminobenzene derivatives of the general formula (II)
HzN X~
Xz I / Q (.II)
in which
Q, X1, X2 and Z1 are as defined above,
1 S if appropriate in the presence of a diluent and if appropriate in the
presence of a
reaction auxiliary,
or when
(b) heterocyclylarenes of the general formula (III)
Zz X'
Xz I / Q (III)
I
H
in which
Q, Xl, X2 and ZZ are as defined above,
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are reacted with heteroarylmethyl halides of the general formula (N)
X3_CH2_Z1 (IV)
S in which
Z1 is as defined above and
X3 represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence
of a
reaction auxiliary,
or when
(c) heterocyclylarenes of the general formula (V)
Z2 X,
(V)
XZ ~ Xa
in which
X1, X2 and Z2 are as defined above and
X4 represents halogen,
are reacted with heteroarenes of the general formula (VI)
HQ-CH2-Z1 (VI)
in which
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Q and Z1 are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence
of a
reaction auxiliary,
and, if appropriate, electrophilic or nucleophilic substitution reactions or
oxidation or
reduction reactions within the scope of the definition of the substituents are
subsequently carned out in a customary manner.
Using, for example, phthalic anhydride and 1-amino-2-fluoro-4-(3,5-dimethyl-
isoxazol-4-yl-methoxy)-benzene as starting materials, the course of the
reaction in
the process (a) according to the invention can be illustrated by the following
formula
scheme:
F O
O F
HzN \ \
\ I / ~ I / .N \
O +
/ O CH3 O I
/ O
O \ CH3
I N
o I ~~N
H3C
O
H3C
Using, for example, 4-(5-chloro-2-fluoro-4-mercapto-phenyl)-1,2-dimethyl-1,2,4-
triazoline-3,5-dione and 2-chloro-5-chloromethyl-thiazole as starting
materials, the
course of the reaction in the process (b) according to the invention can be
illustrated
by the following formula scheme:
H3CN 1 0 H3C n
F
CI
HsC-N Il N ~ \ + ~ SCI HsC-N
O
S N
I
CI H CI
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Using, for example, 3-(2,4-difluoro-S-nitro-phenyl)-4-bromo-1-methyl-S-
trifluoromethyl-1H-pyrazole and furfuryl alcohol as starting materials, the
course of
the reaction in the process (c) according to the invention can be illustrated
by the
following formula scheme:
S
HsC HsC
N-N F N-N F
F3C ~ ~ \ -~ HO F3C ~ I \
O
Br ~ / ~ ~ Br ~ / O
-F
O
N Oz N Oz
The compounds phthalic anhydride and 3,4,5,6-tetrahydro-phthalic anhydride to
be
used as starting materials in the process (a) according to the invention for
preparing
compounds of the formula (I) are known organic chemicals for synthesis.
The formula (II) provides a general definition of the aminobenzene derivatives
further to be used as starting materials in the process (a) according to the
invention
for preparing compounds of the formula (I). In the formula (II), Q, X1, X2 and
Z1
preferably or in particular have those meanings which have already been
mentioned
1 S above, in connection with the description of the compounds of the formula
(I)
according to the invention, as being preferred or as being particularly
preferred for Q,
X1, X2 and Z1.
The starting materials of the general formula (II) are known and/or can be
prepared
by processes known per se (cf. Justus Liebigs Ann. Chem. 733 (1970), 125-140;
DE-
A-2842186; US-A-5344812; US-A-5399543; WO-A-9S 17096; Preparation
Examples).
The formula (III) provides a general definition of the heterocyclylarenes to
be used as
2S starting materials in the process (b) according to the invention for
preparing
compounds of the formula (I). In the formula (III), Q, Xt, XZ and Z2
preferably or in
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particular have those meanings which have already been mentioned above, in
connection with the description of the compounds of the formula (I) according
to the
invention, as being preferred or as being particularly preferred for Q, X 1,
X2 and Z2.
The starting materials of the general formula (III) are known and/or can be
prepared
by processes known per se (cf. EP-A-545206; JP-A-04178373; WO-A-9618618;
Preparation Examples).
The formula (IV) provides a general definition of the heteroarylmethyl halides
further
to be used as starting materials in the process (b) according to the
invention. In the
formula (N), Z1 preferably or in particular has those meanings which have
already
been mentioned above, in connection with the description of the compounds of
the
formula (I) according to the invention, as being preferred or as being
particularly
preferred for Z1; X3 preferably represents fluorine, chlorine, bromine or
iodine, in
particular chlorine or bromine.
The starting materials of the general formula (N) are known organic chemicals
for
synthesis.
The formula (V) provides a general definition of the heterocyclylarenes to be
used as
starting materials in the process (c) according to the invention for preparing
compounds of the formula (I). In the formula (V), X1, X2 and Z2 preferably or
in
particular have those meanings which have already been mentioned above, in
connection with the description of the compounds of the formula (I) according
to the
invention, as being preferred or as being particularly preferred for X1, X2
and Z2; X4
preferably represents fluorine, chlorine or bromine, in particular fluorine or
chlorine.
The starting materials of the general formula (V) are known and/or can be
prepared
by processes known per se (cf. US-A-5281571, WO-A-9206962; WO-A-9618618).
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The formula (VI) provides a general definition of the heteroarenes further to
be used
as starting materials in the process (c) according to the invention. In the
formula (VI),
Q and Z1 preferably or in particular have those meanings which have already
been
mentioned above, in connection with the description of the compounds of the
formula (I) according to the invention, as being preferred or as being
particularly
preferred for Q and Z1.
The starting materials of the general formula (VI) are known organic chemicals
for
synthesis.
The processes according to the invention for preparing compounds of the
general
formula (I) are preferably carried out using diluents. Suitable diluents for
carrying out
the processes (a) to (c) according to the invention are especially inert
organic
solvents. These include, in particular, aliphatic, alicyclic or aromatic,
optionally
halogenated hydrocarbons, such as, for example, benzine, benzene, toluene,
xylene,
chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,
dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl
ether,
diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether
or
ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl
isobutyl
ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile;
amides, such as
N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-
pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or
ethyl
acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol,
ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol
monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol
monoethyl
ether, mixtures thereof with water or pure water.
Suitable reaction auxiliaries for the processes (a) to (c) are in general the
customary
inorganic or organic bases or acid acceptors. These preferably include alkali
metal or
alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides,
hydroxides
or alkoxides, such as, for example, sodium acetate, potassium acetate or
calcium
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acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium
carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate,
potassium
bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium
hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium
hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide,
n-,
i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-,
i-, s- or t-
butoxide; furthermore also basic organic nitrogen compounds, such as, for
example,
trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-
diisopropylamine,
N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-
dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-
methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-
pyridine, S-
ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-
diazabicyclo[2.2.2]-octane (DABCO), 1,5-diazabicyclo[4.3.0]-non-S-ene (DBN) or
1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).
When carrying out the processes (a) to (c) according to the invention, the
reaction
temperatures can be varied within a relatively wide range. In general, the
processes
are carried out at temperatures between 0°C and 200°C,
preferably between 10°C
and 150°C.
The processes (a) to (c) according to the invention are generally carried out
under
atmospheric pressure. However, it is also possible to carry out the processes
according to the invention under elevated or reduced pressure - generally
between
0.1 bar and 10 bar.
For carrying out the processes (a) to (c) according to the invention, the
starting
materials are generally employed in approximately equimolar amounts. However,
it
is also possible for one of the components to be used in a relatively large
excess. The
reaction is generally carried out in a suitable diluent in the presence of a
reaction
auxiliary, and the reaction mixture is generally stirred at the required
temperature for
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several hours. Work-up is carried out by customary methods (cf. the
Preparation
Examples).
The active compounds according to the invention can be used as defoliants,
desiccants, haulm killers and, especially, as weed killers. By weeds in the
broadest
sense there are to be understood all plants which grow in locations where they
are
undesired. Whether the substances according to the invention act as total or
selective
herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in
connection with the following plants:
Dicotyledonous weeds of the eg nera: Sinapis, Lepidium, Galium, Stellaria,
Matricaria, Anthemis, Galinsoga; Chenopodium, Urtica, Senecio, Amaranthus,
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia,
Cirsium, Carduus, Sonchus, .Solanum, Rorippa, Rotala, Lindernia, Lamium,
Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea,
Trifolium,
Ranunculus, Taraxacum.
Dicoyledonous cress of the eg_ nera: Gossypium, Glycine, Beta, Daucus,
Phaseolus,
Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis,
Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the Qenera: Echinochloa, Setaria, Panicum,
Digitaria,
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,
Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,
Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis,
Alopecurus,
Apera.
Monocotyledonous crops of the eg nera: Oryza, Zea, Triticum, Hordeum, Avena,
Seca.le, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
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However, the use of the active compounds according to the invention is in no
way
restricted to these genera, but also extends in the same manner to other
plants.
Depending on the concentration, the compounds are suitable for total weed
control,
for example on industrial terrain and rail tracks and on paths and areas with
or
without tree growth. Equally, the compounds can be employed for controlling
weeds
in perennial crops, for example forests, ornamental tree plantings, orchards,
vineyards, citrus groves, nut orchards, banana plantations, coffee
plantations, tea
plantations, rubber plantations, oil palm plantations, cocoa plantations, soft
fruit
plantings and hop fields, on lawns and turf and pastures and for selective
weed
control in annual crops.
The compounds of the formula (n according to the invention are particularly
suitable
1 S for selective control of monocotyledonous and dicotyledonous weeds in
monocotyledonous and dicotyledonous crops, both by the pre-emergence and by
the
post-emergence method.
The active compounds can be converted into the customary formulations, such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes,
soluble
powders, granules, suspo-emulsion concentrates, natural and synthetic
substances
impregnated with active compound, and microencapsulations in polymeric
substances.
These formulations are produced in a known manner, for example by mixing the
active compounds with extenders, that is to say liquid solvents and/or solid
earners,
optionally with the use of surfactants, that is to say emulsifiers and/or
dispersants
and/or foam formers.
If the extender used is water, it is also possible to use, for example,
organic solvents
as auxiliary solvents. Liquid solvents which are mainly suitable are:
aromatics, such
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as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated
aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene
chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for
example
petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or
glycol,
and also their ethers and esters, ketones, such as acetone, methyl ethyl
ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents, such as
dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid carriers are: for example ammonium salts and ground natural
minerals,
such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or
diatomaceous earth, and ground synthetic minerals, such as finely divided
silica,
alumina and silicates; suitable solid carriers for granules are: for example
crushed
and fractionated natural rocks, such as calcite, marble, pumice, sepiolite,
dolomite
and synthetic granules of inorganic and organic meals, and granules of organic
material, such as sawdust, coconut shells, maize cobs and tobacco stalks;
suitable
emulsifiers and/or foam formers are: for-example nonionic and anionic
emulsifiers,
such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol
ethers, for
example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates and protein hydrolysates; suitable dispersants are: for
example
lignosulphite waste liquors and methylcellulose.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in
the
form of powders, granules or latices, such as gum arabic, polyvinyl alcohol
and
polyvinyl acetate, and also natural phospholipids, such as cephalins and
lecithins, and
synthetic phospholipids can be used in the formulations. Other possible
additives are
mineral and vegetable oils.
It is possible to use dyestuffs, such as inorganic pigments, for example iron
oxide,
titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin
dyestuffs, azo
dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as
salts of
iron, manganese, boron, copper, cobalt, molybdenum and zinc.
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The formulations generally comprise between 0.1 and 95 per cent by weight of
active
compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as
such or in
the form of their formulations, can also be used as mixtures with known
herbicides,
finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example
acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium),
ametryne,
amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin,
azimsulfuron,
benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzofenap,
benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide,
bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole,
c:aloxydim,
carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon,
chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin,
cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop,
clopyralid,
clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,
cycloate,
cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP,
desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-
ethyl),
difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,
dimethachlor,
dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat,
dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin,
ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,
etobenzanid,
fenoxaprop-(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flam-
prop(-methyl), flazasulfuron, fluazifop(-P-butyl), flumetsulam, flumiclorac(-
pentyl),
flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,
fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl, -
sodium),
flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone,
fluthi-
acet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate-
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(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-p-
methyl),
hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapyr,
imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon,
isouron,
isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,
S mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron,
metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin,
metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide,
neburon,
nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon,
oxasulfuron,
oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin,
pentoxazone,
phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn,
propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb,
prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl),
pyrazoxyfen,
pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-
sodium),
quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-
tefuryl),
rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,
sulfometuron(-methyl). sulfosate, sulfosulfuron, tebutam, tebuthiuron,
terbuthylazine,
terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-
methyl),
thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-
methyl),
triclopyr, tridiphane, trifluralin and triflusulfuron.
A mixture with other known active compounds, such as fungicides, insecticides,
acaricides, nematicides, bird repellents, plant nutrients and agents which
improve soil
structure, is also possible.
The active compounds can be used as such, in the form of their formulations or
in the
use forms prepared therefrom by further dilution, such as ready-to-use
solutions,
suspensions, emulsions, powders, pastes and granules. They are used in the
customary manner, for example by watering, spraying, atomizing, scattering.
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The active compounds according to the invention can be applied both before and
after emergence of the plants. They can also be incorporated into the soil
before
sowing.
S The amount of active compound used can vary within a relatively wide range.
It
depends essentially on the nature of the desired effect. In general, the
amounts used
are between 1 g and 10 kg of active compound per hectare of soil surface,
preferably
between S g and 5 kg per ha.
The preparation and the use of the active compounds according to the invention
can
be seen from the examples below.
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Preparation Examples:
Example 1
O
N
O
F / O ~ ~N
CI
(Process (a))
A mixture of 2.0 g (8 mmol) of 1-amino-2-fluoro-4-(2-chloro-pyridin-S-yl-
methoxy)-
benzene, 1.2 g (8 mmol) of phthalic anhydride and 50 ml of acetic acid is
heated
under reflux for 5 hours, then stirred at room temperature for 18 hours and
subsequently heated under reflux for another 4 hours. The mixture is then
concentrated under water pump vacuum, the residue is shaken with water/ethyl
acetate and the organic phase is separated off, washed with water, dried with
sodium
sulphate and filtered. The filtrate is concentrated under water pump vacuum,
the
1 S residue is digested with diisopropyl ether and the crystalline product is
isolated by
filtration with suction.
This gives 1.9 g (62% of theory) of N-(2-fluoro-(2-chloro-pyridin-5-yl-
methoxy)-
phenyl]-phthalimide of melting point 183°C.
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Example 2
FZHC O
N
Fi3C N' 'N
O
F / O ~ ~N
CI
(Process (b))
A mixture of 0.90 g (3.3 mmol) of 4-(2-fluoro-4-hydroxy-phenyl)-2-
difluoromethyl-
1-methyl-1,2,4-triazoline-3,5-dione, 0.65 g (3.3 mmol) of 2-chloro-5-
chloromethyl-
pyridine, 0.55 g of potassium carbonate and 10 ml of N,N-dimethyl-formamide is
stirred at 80°C for 3 hours. After slight cooling, the mixture is then
poured into a
solvent mixture of 1N hydrochloric acid and diethyl ether which has been
admixed
with ice beforehand. After thorough stirring, the crystalline product is
isolated by
filtration with suction.
This gives 0.35 g (26.5% of theory) of 4-[2-fluoro-4-(2-chloro-pyridin-S-yl
methoxy)-phenyl)-2-difluoromethyl-1-methyl-1,2,4-triazoline-3,5-dione of
melting
point 134°C.
Analogously to Preparation Examples 1 and 2 and in accordance with the general
description of the preparation processes according to the invention, it is
also possible
to prepare, for example, the compounds of the formula (Ia) listed in Table 1
below.
Zz \ X'
XZ ~ / Q (Ia)
~Z'
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Table 1: Examples of the compounds of the formula (Ia)
Ex. Q Xl XZ Zl Z2 Melting
point
No. (C)
3 O H F w N (amorphous)
N-
/ CI
O
4 O H F ~ N cH3 73
/ CI F3C NON
CI
5 O H F ~ N (amorphous)
/
CI ~ N
N
CI
6 O N02 F ~ N CH3 170
/ F3C Nw
CI ~ ~N
CI
7 O NH2 F w N ~H3 116
CI F3C NON
CI
8 O H F ~ N FZH ~ ~H3 1 O8
/ p
CI
Br
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Ex. Q X1 X2 Zl Z2 Melting point
No. (°C)
9 O H F ~ N FZHC CH3 90
p Nw
CI ~ ~N
CI
O H F ~N FZH ; ~ H3 106
p Nw
S---~ ~ ~N
CI
11 O H F ~N FZH ; CH3 81
N~
S--C ~ I N
CI CI
12 O H F ~ ~H3 107
N
C ~N/N
SCI
CI
The compound listed in Table 1 as Example No. 6 can, for example, be prepared
as
follows:
5
FsC NOz
O ~ ~N
CI
0.56 g ( 14 mmol) of 60% sodium hydride in mineral oil is added to a solution
of
2.3 g ( 15 mmol) of 2-chloro-5-hydroxymethyl-pyridine in 20 ml of
acetonitrile. The
10 mixture is stirred at room temperature (about 20°C) for 15 minutes,
and then
admixed with 3.4 g (10 mmol) of 4-chloro-3-(2,4-difluoro-5-nitro-phenyl)-1-
methyl-
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5-trifluoromethyl-1H-pyrazole and stirred at room temperature for 4 hours. The
mixture is then diluted with approximately equal amounts of water and ethyl
acetate
to about three times its volume and acidified with 2N hydrochloric acid. The
organic
phase is separated off, washed with saturated aqueous sodium bicarbonate
solution
S and with saturated sodium chloride solution, dried with sodium sulphate and
filtered.
The solvent is carefully distilled off from the filtrate under water pump
vacuum.
This gives 4.6 g (99% of theory) of 4-chloro-3-[4-[(2-chloro-pyridin-5-yl)-
methoxy]
2-fluoro-5-nitro-phenyl]-1-methyl-S-trifluoromethyl-1H-pyrazole of melting
point
170°C.
The compound listed in Table 1 as Example No. 7 can, for example, be prepared
as
follows:
H3C
N~N
F3C ~ ' ~ NHZ
CI ~ /~
F- v _O ~ N
CI
At from 80°C to 90°C, a suspension of 27 g (58 mmol) of 4-chloro-
3-[4-[(2-chloro-
pyridin-5-yl)-methoxy]-2-fluoro-S-nitro-phenyl]-1-methyl-5-tri fluoromethyl-1
H-
pyrazole in a mixture of 120 ml of acetic acid and 60 ml of ethyl acetate is
slowly
metered into a suspension of 32.3 g (0.58 mol) of iron (powder) and 72 ml of
5%
strength aqueous acetic acid. The reaction mixture is stirred at room
temperature
(about 20°C) for 150 minutes and then filtered through Celite~ (filter
aid based on
kieselguhr). The filtration residue is washed with water and ethyl acetate and
the
organic phases are separated off and pooled, washed with saturated aqueous
sodium
bicarbonate solution and saturated aqueous sodium chloride solution, dried
with
sodium sulphate and filtered. The solvent is carefully distilled off from the
filtrate
under water pump vacuum.
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This gives 24.8 g (98% of theory) of 4-chloro-3-[5-amino-4-[(2-chloro-pyridin-
5-yl)-
methoxy]-2-fluoro-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole of melting
point
116°C.
The compound listed in Table 1 as Example No. 4 can, for example, be prepared
as
follows:
H3C
N~N
F3C
CI
F / O ~ ~N
CI
r1 solution of 2.8 g (6.4 mmol) of 4-chloro-3-[5-amino-4-[(2-chloro-pyridin-S-
yl)-
methoxy]-2-fluoro-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole in 20 ml of
tetrahydrofuran is heated to reflux, with dropwise addition of 1.7 ml (12:8
mmol) of
n-pentyl nitrite. The complete reaction mixture is heated under reflux for
another 30
minutes and then concentrated under water pump vacuum. The oily residue is
purified by column chromatography (silica gel, dichloromethane/methanol, vol.:
100:1 ).
This gives 0.65 g (24% of theory) of 4-chloro-3-[4-[(2-chloro-pyridin-5-yl)-
methoxy]-2-fluoro-phenyl]-1-methyl-5-trifluoromethyl-1H-pyrazole of melting
point
73°C.
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Starting materials of the formula (II):
Example (II-1)
H2N
F / O ~ ~N
CI
Step 1
OZN
F / O ~ ~N
CI
A mixture of 8.65 g (55 mmol) of 3-fluoro-4-nitro-phenol, 9.72 g (60 mmol) of
2-
chloro-S-chloromethyl-pyridine, 8.3 g (60 mmol) of potassium carbonate and 1~0
ml
of butanone is heated at 80°C for 10 hours and then concentrated under
water pump
vacuum. The residue is stirred with a solvent mixture of aqueous 2N
hydrochloric
acid, ethyl acetate and diethyl ether, and the crystalline product is isolated
by
filtration with suction.
This gives 9.8 g (63% of theory) of 2-chloro-5-(3-fluoro-4-nitro-
phenoxymethyl)-
pyridine of melting point 174°C.
St_ ep 2
HzN
F / O ~ ~N
CI
9.5 g (33.6 mmol) of 2-chloro-5-(3-fluoro-4-nitro-phenoxymethyl)-pyridine are
initially charged in a mixture of 150 ml of acetic acid and 10 ml of water,
and the
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mixture is heated to 50°C. 9.5 g of iron (powder) are then added a
little at a time,
and the reaction mixture is stirred for about 60 minutes at from 20°C
to 25°C and
then filtered. The filtrate is concentrated, the residue is shaken with
water/ethyl
acetate and the organic phase is washed with water, dried with sodium sulphate
and
S filtered. The filtrate is concentrated under water pump vacuum, the residue
is
digested with petroleum ether and the crystalline product is isolated by
filtration with
suction.
This gives 7.3 g (86% of theory) of 2-chloro-S-(4-amino-3-fluoro-
phenoxymethyl)-
pyridine of melting point 101 °C.
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Starting materials of the formula (III):
Example (III-1 )
FZHC O
N
HsC N II N
\
O /
F OH
Step 1
O
HsC2wO~NiH
I
~N~O
H3 'I~C
H'N ~ \
F OCH3
15.0 g (106.4 mmol) of 1-amino-2-fluoro-4-methoxy-benzene are initially
charged in
400 ml of ethyl acetate and, at room temperature, admixed dropwise with
stirring
with 47 g of trichloromethyl chloroformate ("diphosgene"). The mixture is then
heated under reflux for two hours and subsequently concentrated under water
pump
vacuum. The residue is taken up in 200 ml of acetonitrile and admixed with 23
g of
2-methyl-1-ethoxycarbonyl-hydrazine and 9.8 g of sodium bicarbonate. This
mixture
is then heated under reflux for 16 hours and subsequently concentrated under
water
pump vacuum. The residue is stirred with a mixture of 1N-hydrochloric acid and
diethyl ether and the crystalline product is isolated by filtration with
suction.
This gives 21.5 g (71% of theory) of 4-(2-fluoro-4-methoxy-phenyl)-1-
ethoxycarbonyl-2-methyl-semicarbazide.
1H-NMR (DMSO-D6, 8, ppm): 2.98 (N-CH3).
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Sten 2
H
'-O
~I//
HsC_N~N \
O
F OCH3
A mixture of 21.0 g (83.7 mmol) of 4-(2-fluoro-4-methoxy-phenyl)-1-
ethoxycarbonyl-2-methyl-semicarbazide and 210 ml of 4N aqueous sodium
hydroxide solution is heated at 80°C for 20 minutes and then cooled to
10°C and
subsequently admixed with 70 ml of cone. hydrochloric acid. The mixture is
then
shaken with methylene chloride, and the organic phase is washed with water,
dried
with sodium sulphate and filtered. The filtrate is concentrated under water
pump
vacuum, the residue is digested with diethyl ether and the crystalline product
is
isolated by filtration with suction.
This gives 13.9 g (79% of theory) of 4-(2-fluoro-4-methoxy-phenyl)-1-methyl-
1,2,3-
triazoline-3,5-dione.
1H-NMR (DMSO-D6, 8, ppm): 3.81 (O-CH3).
Step 3
FZHC O
N
HsC-N II N \
O ( /
F OCH3
Chlorodifluoromethane is passed through a mixture, heated to 100°C, of
14.0 g
(58.6 mmol) of 4-(2-fluoro-4-methoxy-phenyl)-1-methyl-1,2,3-triazoline-3,5-
dione,
8.5 g of potassium carbonate and 50 ml of N,N-dimethyl-formamide for three
hours.
After slight cooling, the mixture is poured into ice-water, acidified with 2N
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hydrochloric acid and shaken with ethyl acetate. The organic phase is
separated off,
washed with water, dried with sodium sulphate and filtered. The filtrate is
concentrated under water pump vacuum and the residue is separated by column
chromatography (silica gel, ethyl acetate/hexane, vol. 1:2).
This gives (as second fraction) 4.0 g (24% of theory) of 4-(2-fluoro-4-methoxy-
phenyl)-2-difluoromethyl-1-methyl-1,2,3-triazoline-3,5-dione of melting point
88°C.
Step 4
FZHC O
N
HsC_N~N \
O ~ /
F OH
2.0 g (6.9 mmol) of 4-(2-fluoro-4-methoxy-phenyl)-2-difluoromethyl-1-methyl-
1,2,3-
triazoline-3,5-dione are dissolved in 30 ml of methylene chloride, and this
mixture is
added dropwise with stirnng to a solution of 3 g of boron trifluoride in 30 ml
of
methylene chloride. The reaction mixture is then stirred at room temperature
for
6 hours. After addition of 50 ml of water, the organic phase is separated off,
washed
with water, dried with sodium sulphate and filtered. The solvent is carefully
distilled
off from the filtrate under water pump vacuum.
This gives 1.6 g (84% of theory) of 4-(2-fluoro-4-hydroxy-phenyl)-2-
difluoromethyl-
1-methyl-1,2,3-triazoline-3,5-dione of melting point 141°C.
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Use examples:
Example A
Pre-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of
active
compound is mixed with the stated amount of solvent, the stated amount of
emulsifier is added and the concentrate is diluted with water to the desired
concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the
soil is
sprayed with the preparation of active compound such that the particular
amounts of
active compound desired are applied per unit area. The concentration of the
spray
liquor is chosen so that the particular amounts of active compound desired are
applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in
comparison to the development of the untreated control.
The figures denote:
0 % - no effect (like untreated control)
100 % - total destruction
In this test, for example, the compounds of Preparation Example l, 2, 3 and 4
exhibit
strong activity against weeds, and some of them are tolerated well by crop
plants,
such as, for example, maize and wheat.
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Example B
Post-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of
active
compound is mixed with the stated amount of solvent, the stated amount of
emulsifier is added and the concentrate is diluted with water to the desired
concentration.
Test plants of a height of 5 - 15 cm are sprayed with the preparation of
active
compound such that the particular amounts of active compound desired are
applied
per unit area. The concentration of the spray liquor is chosen so that the
particular
arr~ounts of active compound desired are applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in
comparison to the development of the untreated control.
The figures denote:
0% = no effect (like untreated control)
100% = total destruction
In this test, for example, the compounds of Preparation Example 2, 3, 4 and 5
exhibit
strong activity against weeds, and some of them are tolerated well by crop
plants,
such as, for example, wheat.
