Note: Descriptions are shown in the official language in which they were submitted.
5~7 ~
OOZo 30,703
USE OF UREA DERIVATIVES AS SELECTIVE HERBICIDES IN CEREALS
The present invention relates to the use of substituted
aryl ureas as selective herbicides in cereals such as wheat,
rye, oats and barley.
It is known (U~S. 23655,445) that various aryl urea
derivatives are suitable as total herbicides, especially for
destroying all grass and weeds which usually grow for ;nstance
on railway tracks and in drainage ditchesJ where the aim is
to achieve complete destruction of all plant growthO
Preferred derivatives are said to be aryl ureas substituted
in the 3- or 4-position. The abovementioned patent specification
also mentions 3-(3,5-dichloro-4-methoxyphenyl)-1,1-dimethylurea,
but no specific areas of use are disclosed. From more recent
publications (e.g. German Laid~Open Applications DOS 1,905,598
and 1,9189114 and German Published Application DAS 1,966,298)
it is known that certain aryl urea derivatives are also suitable
for use in cereal crops although they are stated to be total
herbicides in earlier publications~ However, these aryl urea
derivatives are only substituted in the 3- or 4-position. The
impression has thus been created and all commercial urea
herbicides confirm this - that the only aryl urea derivatives
likely to be successful in cereals are those bearing one or at
most two substituents in the 3- and 4-position on the aryl ring
There thus existed a prejudice against using highly subst;tuted
1--
7~
~s~
aryl urea derivati~es in this special field.
We have now surprisingly found a process ~or protecting
a cereal crop from weeds, wherein a selectively phytotoxic amount
of a urea derivative of the formula
Rl_o ~ C0 N ~ 3
Cl
wherein Rl denotes methyl or ethyl and R2 denotes methyl,
methoxy or butynyl is applied to the crop area. "Cereal crops",
in this context, are taken to be wheat, rye, barley and oats.
The compounds of the invention are particularly suitable
for controlling broadleaved and grassy weeds of the Alopecurus
spp., Apera spica venti, Avena fatua, Lamium spp., Matricaria
spp., and Stellaria media species.
The chemically closest known urea derivative used as
a selective cereal herbicide is l-(3-chloro-4-methoxyphenyl)-3,3-
dimethylurea disclosed in Swiss 466,~43. Compared with this
active ingredient, the compounds of the invention have better
selectivity in cereals combined with a similar or superior
action on grassy weeds.
The compounds of the invention are thus a valuable
extension of the art.
The following compounds are examples of active ingredients
according to the invention:
1-(3,5-dichloro-4-methoxy)-phenyl-3~methylurea
. ~ .
-
~L~5978~
O~Z~ 30~703
1-(3,5~dichloro-4-ethoxy)-phenyl-3 methylurea
1-(3J5-dichloro-4-methoxy) phenyl-3-methyl-30methoxyurea
1-(395-dichloro-4-methoxy)-phenyl-3,3-dimethylurea
1-(3,5-dichloro-4-ethoxy)-phenyl-393 dimethylurea
1-(3,5-dichloro-4-ethoxy)~phenyl-3-methyl~3-(2-butynyl)-ureaO
The active ingredients are obtained for instance by
reaction of 3,5-dichloro-4-methoxyphenyl isocyanate or 3,5-
dichloro-4-ethoxyphenyl isocyanate with methylamine, dimethyl~
amine or O,N-dimethylhydroxylamine in inert solvents.
The isocyanates used as starting materials are obtained
by conventional methods by phosgenation of the art compound
3,5-dichloro-4-methoxyaniline (C. de Trat, HelvO chim Acta~
30, 232, 1947; F.B. Mallory and SOP~ Varinbi, J. Org. ChemO,
28, 1~56, 1963) or 3,5-dichloro-4-ethoxyaniline (GO Bargellini,
Gazz. Chim. Ital., 59, ~6, 1929)
The preparation o~ the compounds of the invention is
illustrated below.
1~(3,5-dichloro-4-methoxy)-pheny`1-3 3-dimethylurea
At 10 to 15C, a solution of 218 parts ~by weight) of
3,5-dichloro-4-methoxyphenyl isocyanate in 750 parts of dry
benzene is dripped over a period of 1 hour into a solution o~
54 parts o~ dimethylamine in 750 parts of dry benzeneO The mixture
is stirred for 30 minutes at room temperature and for 1 hour
at 50C. The urea derivative is precipitated, cooled, suctîon
filtered, washed with 100 parts of benzene and then with 100
parts of n-pentane, and driedO
_3~
~ O S~ 7 80 oOz, 30,703
There is obtained 260 parts of the desired compound;
mOp.o 194 - 196C~
The following compounds are obtained analogously:
NoO Formula m~pO in C
(recrystallized ~rom)
,, ~
: Cl
3 ~ NH-C0-NH-CH3 188-90 (ethanol/water)
Cl
Cl
CH
3 C2H5- ~ NH-C0-N 3 205-208
Cl
: Cl
4 C2H5 0 ~ NH-C0-NH-CH3 201 (ethanol~water)
Cl
Cl
. 5 C2H5 0 ~ NH-C0-N 3 . 54-56
y ~ CH-C-CH
Cl CH3
1-~3?5-dichloro-4-methsx~)-phenyl-3-methy_-3-met~hoxyurea
At 0VC~ a solution of 506 parts o~ sodium.hydroxide i.n
15 parts of water, and subsequently 100 parts Or methylene
chloride are added to a solution of 11.7 parts o~ 0,N-dîmethyl-
hydroxylamine chlorohydrate in 25 parts of water.
This well stirred suspension has dripped.into.ît at 0C
to +10C a solution of 21.8 parts of 3,5-dichloro-4-methoxy-
: phenyl isocyanate in 50 parts of methylene chloride~ The mixture
is stirred for 1 hour at room temperature and the organîc phase
. -4-
~L~5~78(~
O.Z~ 30~703
is then separated9 washed with water, drled (Na2S04) and con-
centrated O
There is obtained 25 parts of the desired compound;
m~pO~ 78Co
~ Application may be effected ~or instance in the form of
: directly sprayable solutions, powders, suspensions (inelud;ng
high-percentage aqueous, oily or other suspensions), dispersions9
emulsions, oil dispersions, pastes9 dusts3 broadcasting agents,
or granules by spraying, atomizing~ dusting, broadcasting or
.10 watering~ The forms of application depend entirely on the purpose
~or which the agents are being used; in any case they should
ensure a fine distribution of the active ingredientO
For the preparation of ~dutions 9 emulsions, pastes and
oil dispersions to be sprayed direct, mineral oil fractions
of medium to h;gh boiling point, such as kerosene or diesel
oil, further coal-tar oils, etc and oils of vegetable or animal
origin, aliphatic, cyclic and aromatic hydrocarbons such as
benzene, toluene, xylene, paraff;n, tetrahydronaphthalene, .
alkylated naphthalenes and their derivatives such as methanol,
ethanol, propanol, butanol, chloroform, carbon tetrachloride,
cyclohexanol, cyclohexanone, chlorobenzene~ isophorone, etcO 9
and strongly polar solvents such as dimethylformamide, d;methyl
sulfoxide, N-methylpyrrolidone, water9 etcO are su;tableO
Aqueous formulations may be prepared ~rom emulsion con-
centrates, pastes, oil d;spersions or wettable powders by
adding waterO To prepare emulsions 3 pastes and o;l dispersions
the ingredients as such or dissolved in an oil or sol~ent may
~0597BQ oozo 30 9 703
be homogenized in water by means of wetting or dispersing
agents, adherents or emulsifiersO Concentrates which are
suitable for dilution with water may be prepared from active
ingredient 5 wetting agent, adherent~ emulsifying or dispersing
agent and possibly solvent or oilO
Examples of surfactants are~ alkali metal, alkaline earth
metal and ammonium salts o~ ligninsulfonic acid, naphthalene
sulfonic acids, phenolsulfonic acids, alkylaryl sulfonates,
; alkyl sulfates, and alkyl sul~onates, alkali metal and alkaline
earth metal salts of dibutylnaphthalenesulfon;c acid, lauryl
ether sulfate, fatty alcohol sul~ates,.alkali meta~ and alkaline
earth metal salts of fatty acids, salts of sulfated hexadecanols,
heptadecanols, and octadecanols, salts.of sul~at.ed fatty alcohol
glycol ether, condensation products or sulfonated naphthalene
and naphthalene derivatives with formaldehyde~.condensat;on
products of naphthalene or naphthalenesulfonic acids.with
phenol and formaldehyde, polyoxyethylene octylphenol ethers,
ethoxylated isooctylphenol, ethoxylated.octylphenol..and ethoxyl~
ated nonylphenol, alkylphenol polyglycol ethers, tributylphenol
polyglycol ether~, alkylaryl polyester alcohols, isotridecyl
alcohols, fatty alcohol ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl.ethers, ethoxylated.polyoxy-
propylene, lauryl alcohol polyglycol ether acetal3 sorbîtol
esters, lignin~ sulfite waste liquors and methyl celluloseO
Powders, dusts and broadcasting agents may be prepared
by mixing or grinding the active ingredients with a.solid
carrierO
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59 ~ ~
O~ZO 30,703
Granules, e.g~g coated, impregnated or homogeneous gra-
nules 9 may be prepared by bonding the active ingredients to
solid carriersO Examples Or solid carriers are mineral earths
such as silicic acid, silica gels9 silicates3 talc, kaolin,
Attaclay~ limestone~ lime, chalk, bole9 loess9 clay, dolomite,
diatomaceous earth, calcium sulfate, magnesium sulfate~ magnesium
oxide, ground plastics, fertilizers such as ammonium sul~ate~
ammonium phosphate, ammonium nitrate, and ureas, and vegetable
products such as grain flours, bark meal, wood meal, and nutshell
meal, cellulosic powders, etcO
The formulations contain from 0~1 to 95 9 and preferably
0.5 to 90, % by weight of active ingredientO
There may be added to the compositions or individual
active ingredients (if desired, immediately before use (tank-
mix)) oils of various types, wetting agents or adherents,
herbicides, fungicides, nematocides, insecticides, bactericides3
trace elements, fertilizers, antifoams (eOg., silicones), growth
regulators, antidotes and other herbicidally e~ective compounds
such as
substituted alkylsulfonylglycolic amides and imides
substituted alkylaminosulfonylglycolic amides:and imides
substi~uted acetanilidoalkyl sul~ites
substituted anilines
substituted azides
substituted aryloxycarboxylic acids and aryloxythlocarboxylic
acids and salts; esters and amides thereo~
substituted ethanols, ethenols
--7--
5~
OOZ~ 30,703
substituted ethers
substituted arsonic acids and arsenic acids and salts, esters
and amides thereof
substituted benzene sulfonamides
substituted benzimidazoles
substituted benzisothiazoles
: dihydrobenzofuranyl alkylamino sulfonates
substituted benzothiadiazinone dioxides
substituted benzoxazines
substituted benzoxazinones
substituted benzoxazoline thiones
substituted benzothiadiazoles
substituted benZothiaZQlinyl alkyl carboxylic acids and salts,
esters and amides thereof
substituted biurets
substituted quinolines
substituted carbamates
` substituted aliphatic or cycloaliphatic carboxylic acids and
thiocarboxylic acids and their salts, esters and amides
substituted aromatic carboxylic acids and thiocarbox~Jl:ic acids
and their salts, esters and amides
substituted carbamoylalkylthiol- or -dithiophosphates
substituted quinazolines
substituted cycloalkylamidocarbothiolic acids and their salts,
esters and amides
substituted cycloalkylcarbonamidothiazoles
substituted dicarboxylic acids and their salts, esters.and am;des
-8-
~1~S978~1~
OOZo 30~703
substituted dihydrobenzofuranyl sulfonates
substituted dihydropyrane diones
substituted disulfides
substituted dioxanes
substituted dipyridylium salts
substituted dithiocarbamates
substituted dithiophosphoric acids and their salts, esters
and amides
substituted ~luorenecarboxylic acids and their salts, esters
and amides
substituted ureas
substituted hexahydro-lH-carbothioates
hexahydro-lH-carbothioates
substituted hydantoins
substituted hydrazides
substituted h~drazonium s~lts
substituted h~dro~uranones
substituted isoxazole pyrimidones
substituted imidazoles
substituted imidazolidinedione carboxamides
substituted isothiazole p~rimidones
substituted ketones
substituted naphtho~uinones
substituted naphthalic anhydrides
substituted aliphatic nitriles
substituted aromatic nitriles
substituted oxadiazoles
~59780 O~Z~ 30,703
substituted oxadiazinones
substituted oxadiazolines
substituted oxadiazolidine diones
substituted oxazolidines
substituted oxadiazine diones
substituted oxazole pyrimidinones
substituted phenols and their salts and esters
substituted phosphonic acids.and their salts, esters and amides
substituted phosphonium chlorides
substituted phosphonalkyl glycines
substituted phosphites
substituted phosphoric acids and their salts, esters and.amides
substituted piperidines
substituted pyrazoles
. substituted pyrazole alkylcarboxylic acids and their salts,
esters and amides
substituted pyrazolium salts
substituted pyrazolium alkyl sul~`ates
~ substituted pyridazines
: 20 substituted pyridazones
substituted pyridine carboxylic ac.ids and their salts, esters
and amides
substituted pyridines
substituted pyridine carboxylates
substituted pyridinones
~ubstituted pyrimidines
substituted pyrimidones
--10--
7 ~
O.Z. 30,703
substituted pyrrolidine carboxylic acid and its salts, esters
and amides
substituted pyrrolidines
substituted pyrrolidones
substituted arylsulfonic acids and their salts, esters and amides
substituted sulfamates
substituted styrenes
substituted sulfonyl toluidides
substituted tetrahydrooxadiazine diones
substituted tetrahydroxadiazole.diones
substituted tetrahydromethanoindenes
substituted tetrahydroxadiazole thiones
substituted tetrahydrothiadiazine thiones
substituted tetrahyd~othiadiazole diones
substituted aromatic thiocarbonylamides
substituted thiobenzamides
substituted thiocarboxylic acids and their saltæ, esters and
amides
substituted thiol carbamates
substituted thioureas
substituted thiophosphoric..ac.ids and their salts, esters and
amides
substituted triazines
substituted triazinones
substituted triazoles
substituted uracils
substituted uretidine diones
~59~80
0,Z. 30,703
chlorates, and
substituted azetidine carbothioatesO
The last-mentioned herbicidal compounds may.also be.applied
before or after the active ingredients or compositions thereof
accordin~ to the inventionO
These agents may be added to the herbicides according
to the invention in a ratio by weight of ~rom 1:10 to 10:1.
i The same applies to oils, wetting agents and adherents~ fungî-
cides, nematocides, insecticides, bactericides, an~idotes and
growth regulatorsO
The new compositions have a strong herbicîdal action
and may therefore be used.as weedkillers..or for.controlling
the growth of unwanted piantsO Whether the.new active ingredients
are used as total or selective agents depends in essence on the
amount of ingredient used per unit.area.
By weeds and unwanted plant growth are meant all mono-
cotyledonous and dicotyledonous plants which.grow in loci
where they are not desired.
The agents according to..the invention may thererore be
used for controlling ~or instance
Gramineae, such as
Gynodon spp. . ......... Dactylis 5pp q
: Digitaria spp~ . Avena spp.
Echinochloa spp~ Bromus Spp4
Setaria spp. Uniola spp.
Panicum sppO Poa spp~
Alopecurus sppO Leptochloa sppO
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:1~597~0
0,Z. 30~703
Lolium sppO Brachiaria sppO
Sorghum spp, Eleusine sppO
Agropyron spp. Cenchrus sppO
Phalaris sppO Eragrostis spp.
Apera sppO Phra~mitres communis
etc.;
Cyperaceae, such as
Carex 8ppo Eleocharis sppO
Cyperus spp~ Scirpus spp~
: 10 etc~;
dicotyledonous weeds, such as
Malvaceae, eOg. 9
Abutilon theoprasti Hibiscus spp.
Sida 9pp. Malva spp.
etc.;
Compositae, such as
Ambrosia sppO Centaurea spp~
Lactuca SPPD Tu~silago spp.
Senecio spp. Lapsana communis
Sonchus spp. Tagetes sppO
Xanthium sppO Erigeron spp.
Iva spp. Anthemis spp.
Galinsoga sppO Matricaria spp.
Taraxacum spp. Artemisia sppO
Chrysanthemum spp. Bidens spp~
Cirsium spp. etc.;
Convolvulaceae, such as
: -13-
~S9~'80
O.Z. 30,703
Convolvulus sppO Cuscuta 5pp.
Ipomoea spp. Jaquemontia tamnifolia
et c O ,
Cruciferae 9 such as
Barbarea vulgaris Arabidopsis thaliana
Brassica spp. Descurainia spp.
Capsella 5pp. Draba spp.
Sisymbrium spp. Coronopus didymus
Thlaspi spp. Lepidium spp.
Sinapsis arvensis Raphanus spp.
etc.;
Geraniaceae, such as
Erodium spp. Geranium spp.
etc.;
Portulacaceae, such as
Portulaca spp. etc.;
Primulaceae, such as
Anagallis arvensis Lysimachia spp.
etc.
Rubiaceae, such as
Richardia spp. Diodia spp.
Galium spp. etc/;
Scrophulariaceae~ such as
Linaria sppO Digitalis spp.
Veronica spp~ etc 7;
Solanaceae, such as
Physalis spp. Nicandra spp.
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1~35~780
OoZO 30,703
Solanum sppO Datura sppO
etc.;
; Urticaceae, such as
Urtica spp.
Violaceae, such as
Viola spp. etc.;
Zygophyllaceae, such as
Tribulus terrestrls etc.;
Euphorbiaceae, such as
Mercurialis annua Euphorbia spp.
Umbelliferae, such as
Daucus carota Ammi majus
Aethusa cynapium etc.;
Commelinaeae, such as
Commelina spp. etc.;
Labiatae, such as
Lamium sppO Galeopsis sppO
etc.;
LeguminosaeD ~uch as
Medicago spp. Sesbania exaltata
Trifolium spp. Cassia spp.
Vicia spp. I,athyruæ spp.
etc.;
Plantaginaceae, such as
Plantago sppO etc.;
Polygonaceae, such as
Polygonum sppO Fagopyrum spp.
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7 ~
O.Z. 30,703
Rumex sppO etc.;
Aizoaceae, such as
Mollugo verticillata etc.;
Amaranthaceae, such as
Amaranthus sppn etc.;
Boraginaceae, such as
Amsinckia sppO Anchusa spp~
Myostis spp. Lithospermum spp.
etcO;
Caryophyllaceae, such as
Stellaria spp. Silene spp.
Spergula spp. Cerastium spp.
Saponaria spp. Agrostemma githago
Scleranthus annuus etc.;
Chenopodiaceae, such as
Chenopodium Sppl Atriplex spp.
Kochia spp. Monolepsis nuttalliana
Salsola Kali etc.;
Lythraceae, such as
Cuphea spp. etc.;
- Oxalidaceae, such as
Oxalis spp.
Ranunculaceae~ such as
Ranunculus spp. Adonis spp,
Delphinium spp. etc.;
Papaveraceae, such as
Papaver spp. Fumaria of~icinalis
-16-
1~35~780
O.Z. 303703
etc.;
Onagraceae, such as
Jussiaea spp. etc.;
Rosaceae, such as
Alchemillia sppO Potentilla spp.
etc.;
Potamogetonaceae, such as
Potamogeton spp. etc.;
Najadaceae, such as
Najas spp. etcc;
Equisetaceae
Equisetum spp. etct;
Marsileaceae, such as
Marsilea quadrifolia e~c~;
Polypodiaceae, such as
Pteridium quilinum
Alismataceae, such as
; Alisma spp. Sagittaria sagittifolia etc.
The selective herbicidal action and the excellent compa-
tibility o~ these active ingredients will be apparent ~rom the~ollowing examples. The good selectivity of these compounds is
particularly clear ~rom the fact that the high applicat,ion rates
used to destroy extremely resistant weeds cause no marked damage
to cereal plants.
EXAMPLE 1
The plants wheat (Triticum,aestivum), barley (Hordeum
vulgare), slender ~oxtail (Alopecurus myosuroides), wild oats
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~ ~5~7~
O.Z. 30,703
(Avena fatua), henbit (Lamium amplexicaule), chamomile (Matricaria
chamomilla)) wild mustard (Sinapsis arvensis) and chickweed
(Stellaria media) were treated in the open at a growth height
of from 3 to 20 cm with 1~5 kg/ha of each Or the following
compounds, each being dispersed or emulsified in 500 liters of
water per hectare:
1 1-(3,5-dichloro-4-methoxy)-phenyl-3,3-dimethylurea
1-(3,5-dichloro-4-methoxy) phenyl-3 methylurea
7 1 (3,5-dichloro-4-methoxy)-phenyl-3-methyl-3-methoxyurea
10 6 1-(3-chloro-4-methoxy)Dphenyl-3~3-dimethylurea
(comparative agent)
After 2 to 3 weeks it was ascertained that active.ingredients
1,2 and 7 had better crop plant compatibility than compound 6,
combined with the same herbicidal action.
; The results are given below:
Active.in~redient _ _ 1 2 6 7
~" _
Crop plants
Hordeum vulgare 0 5 10 0
Triticum aestivum 0 0 20 0
Unwanted plants
Avena fatua 95 90 95 95
Alopecurus myosuroides90 80 85 100
Lamium amplexicaule 100 100 85 100
Matricaria chamomilla100 95 100 100
Sinapis arvensis 100 100100 100
Stellaria media 100 100100 100
: 0 = no damage
100 - complete destruction
-18-
~5~7fl~
OOZ. 30,703
EXAMPLE 2
In the greenhouse, loamy sandy soil was filled into pots
and sown with the seeds o~ wheat (Triticum aestivum) and Italian
rye~rass (Lolium multi~lorum)~ The soil was then immediately
treated with 2 kg~ha of each of active ingredients 296 and 7,
each being dispersed in 500 liters of water per hectare. The
soil was kept well watered during the experiment.
After 4 to 5 weeks it was ascertained that active ingredients
2 and 7 had better crop plant compatibility than compound 6,
combined with the same herbicidal action~
The results are given below:
Active in~redient _ `2 6 -7
Crop plant;
Triticum aestivum 20 80 20
Unwanted plant:
Lolium multi~lorum 100 100 100
0 = no damage
100 = complete destruction
EXAMPLE 3
An agricultural plot was sown with the seeds of rye
(Secale cereale), barley (Hordeum vulgare)~ slender foxtail
(Alopecurus myosuroides), common lambsquarters (Chemopodium
album~, henbit (Lamium amplexicaule), chamomile (Matricaria
chamomilla), wild mustard (Sinapis arvensis) and chic~weed
(Stellaria media). The soil was then immediately treated with
3 kg/ha Or active ingredient 1 dispersed in 500 liters of water
per hectare.
-19-
~5978~)
O.Z. 30,703
After 4 to 5 weeks it was ascertained that the active
ingredient had almost completely destroyed all the unwanted
plants, but the barley plants continued to grow undamagedO
The results are given below:
Active in redient
g
~ .
Hordeum vulgare 0
Secale cereale 0
Unwanted plants:
10 Alopecurus myosuroides 90
Chenopodium album 100
Lamium amplexicaule 95
Matricaria chamomilla 100
Sinapis arvensis 100
Stellaria media 100
0 - no damage
: 100 = complete destruction
The following compounds have an analogous action:
1-(3,5-dichloro 4-ethoxy)-phenyl-3,3-dimethylurea
1-(3,5~dichloro-4-ethoxy) phenyl-3-methylurea
1-(3,5-dichloro-4-ethoxy)-phenyl-3-methyl-3-t2-butynyl) urea
EXAMPLE 4
In the greenhouseS various plants were treated at a growth
height of ~rom 6 to 15 cm with 2~0 kg~ha of each of the following
active ingredients, each being dispersed or emulsified in 500
liters of water per hectareo
1 1-(3,5-dichloro-4-methoxy)-phenyl-3,3-dimethylurea
-20-
1~59780
O~Z0 30,703
6 N (3-chloro-4-methoxyphenyl)-N',N'-dimethylurea
(comparative agent)
The plants were kept well watered during the experimentO
After 4 to 5 weeks it was ascertained that active ingredient
1 had better crop plant compatibility than compound 6 9 combined
with the same or superior herbicidal actionO
The results are given below:
Active ingredient 1 6
. k~/ha 2.0~0O _
- 10 Crop plantc
Gossypium hirsutum 10 80
Unwanted plants:
Lolium multiforum 95 90
Echinochloa crus galli 100 100
Alopecurus myosuroides 95 95
Bromus tectorum 100 85
0 = no damage
100 = complete destruction
EXAMPLE 5
In the greenhouse, loamy sandy soil was filled into pots
and sown with various seeds. The soil was then immediately treated
with lo 0 kg/ha of the compound of the formula
Cl
H3C0 ~ NH-G-N 3 ~I)
~ 0 CH3
dispersed in 750 liters of water per hectareO 80 to lOO mm of
precipitate was added during the experimentO
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~ 5~ ~ 8~ 0zO 30.703
After 4 to 5 weeks it was ascertained that the compoundhad a strong herbicidal action combined with good crop plant
compatibilityO
The results are given below:
Active ingredient
k~!ha _ 1,O
Crop plants:
Gossypium hirsutum 0 (5)
Glycine max 6 (3)
Unwanted plants
.
Digitaria sanguinalis 100 (2)
Echinochloa crus-galli 80 ~5)
Panicum virgatum go (1)
Cyperus difformis 100 (1)
0 = no damage
100 = complete destruction
(the figures in brackets indicate the number of experiments;
in the case of more than one experiment, the score given is the
average)
EXAMPLE 6
An agrioultural plot was sown.with various see.ds. The soil
was then immediately treated with 2.0 kg/ha of compound I dis-
persed in 750 liters of water per hectareO 15 to 20 mm of
precipitate fell during the experiment~
After 4 to 5 weeks it was ascertained that the compound
had a good herbicidal action combined with favorable crop
plant c.ompatibilityO
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5~ 7 ~ ~
O,Z. 30,703
The results (preemergence action) are given below:
Active ingredient
kg/ha_ 2.0
; Crop plants:
Gossypium hirsutum 4 (11)
Glycine max 10 (3)
Unwanted plants:
Echinochloa crusogalli 88 (8)
Amaranthus retro*lexus 77 (3)
10 Galium aparine 78 ~8)
, . . . .
Polygonum persicaria 85 (8)
O = no damage
~ 100 = complete destruction
: (The figures in brackets indioate the number o~ experiments;
the score given is the average)
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