Note: Descriptions are shown in the official language in which they were submitted.
The present invention relate~ to com~ounds from
the group of 2-oxo-4-thiono~5-imino-imidazolidines and, in
particular, 4-thioparabanic acid derivatives, a process of
preparing the same and herbicides containing the same.
It is an object of the invention to provide new
4-thioparabanic acid derivatives which are applicable as
herbicidal agents against undesirable weeds in cultivated
plantings, which have the necessary tolerance toward useful
plant:s, and to also provide methods for preparing such
compounds by reactions easy, as well as inexpensive to carry
out.
The 4-thioparabanic acid derivatives of this
invention have the formula
R ~S
N - C
C C = ~ - ~
~ ~ /
0 N
~H3
in which R stands for an aromatic radical, which may be
substituted.
Preferred compounds of the invention are such in
which R is an aromatic radical of up to 10 C-atoms, a
substituted aromatic radical having up to 9 C-atoms, and 0-3
hetero-atoms.
Especially preferred are compourlds in which R is
an aromatic radical with up to 6 C-atoms, a substituted
aromatic radical with up to 9 C-atoms, and 0-3 herero-atoms.
- 1 - .~
'rhe erfective agents according to the ir~vention
may be used for selective weed control, while leaving useful
and decorative plants in agricultural and hort;cultural
plant:ings unaffected, when applied in appropriate amounts.
The herbicidal effectiveness also applies to
high].y yield-reducing weed grasses and dicotyledonous
weeds. From the group of sweet weed grasses, e.g.,
Lolium-species, Poa annua, Alopecurus myosuroides, Avena
fatua, some millets, e.g., Digitaria sanguinalis and
Echinochloa crus-galli, and from the ~roup of "sour" grasses
which are important in rice growing, e.g., Cyperus iria.
Other examples Çor dicotyledonous weeds are cruciferae,
e.g., Sinapis arvensis, Capsella bursa-pastoris,
Thlaspi arvense, Raphanus raphanistrum, and others,
compositae, e.g., Centaurea cyanus, Matricaria inodora,
Chrysanthemum segetum, Galinsoga parviflora, Senecio
vulgaris, and others, knot weeds, e.g., Polygonum
persicaria, labiatae, e.g., Lamium purpyreum, as well as
Chenopodium album, Stellaria media, Galium aparine,
Amaranthus retroflexus, and others.
~ he active compounds according to the invention
have proven useful as herbicidal agents in cultivated
plantings, such as summer barley, winter wheat, rice,
cotton, soybean, potatoes, cultured millet especially
sorghum millet~ corn and leguminous plants such as lucerns,
beans, peas, and carrots.
The preparation of the compounds according to the
invention is accomplished by reacting organic thio-oxanilic
acid-nitriles with methylisocyanate.
The process for preparing compounds of the formula
R S
N - C
C C = N - H
~\ /
O N
CH3
wherein R stands for an aromatic radical, which may be
substituted, is characterized by:
(a) reacting a thio-oxanilic acid-nitrile of the
formula
R - NH - C
CN
with methylisocyanate (with R having the meaning explained
above) and
(b) adding, if desired, a solvent promoting
cyclization during or after the reaction described under (a).
The chemical reaction occurring depends on the
reaction temperature, the medium in which the reaction
proceeds, and the purity of the starting materials (thio-
oxanilic acid-nitrile or isocyanate) and, especially the HCl
content thereoi, which may be present from the process of
1:~ 5~
producing the reactants and from the controlled, repro-
ducible addition. The HCl has a reaction-retardant eEEect,
provided that no basic reaction medium, such as pyridine, is
used. However, an HCl content of up to 1000 ppm can
generally be tolerated, calculated on the HCl-containing
component. On the other hand, it is frequently desirable to
add 50-1000 ppm, preferably 150-250 p~m HCl, calculated on
the total amount of the methylisocyana~te to be reacted, in
order to suppress a further Feaction at the imine-
nitrogen ~in the 5-position) by ~xcessive isocyanate.
The reactions are advantageously carried out at a
temperature range from ~-100C, pre~erably at temperatures
about ~0C.
Pyridine or pyridine bases, such as the
piccolines, used as reaction media, guarantee in general a
rapid and smooth course of the reactions. However, it is
frequently possible to-use the isocyanate to be reacted as
the reaction medium, if the isocyanate has a sufficiently
large capability of dissolving the thio-oxanilic acid-
~0 nitrile. When the reaction is carried out in an aprotic,anhydrous solvent, e.g., benzene, toluene, tetrahydrofuran,
and the lilce, as well as in reactions without a solvent, in
the lower temperature range, cyclization, in general, does
not occur and compounds of the formula
R ~ S
N - C
¦ CN
O = C
NH
C113
~ ~ _ _ _ . _ _ _ . . _ . . _ _ .... .. _ . , .. ., . . . .. . .. . ... . . . , .. _ _ . . _
s~
are formed which spontaneously are converted into the cyclic
product when they are dissolved, or recrystallized in
solvents promoting cyclization, such as ethanol, aqueous
tetr~hydrofuran, but also in basic solvents, e.g., pyridine
or pyridine bases.
The thio-oxanilic acid-nitriles are derivable from
the corresponding isothiocyanates, which may be substituted
at the aromatic radical. Their preparation is carried out
according to or in an analogous manner to the prescription
of A. Reissert and K. Bruggemann in Ber. dtsch. Chem. Soc.
57, 9~1 (192~).
Phenyl isothiocyanate, or phenyl isothiocyanate
subst:ituted at the aromatic radical, is stirred in alcoholic
solut:ion with an aqueous solution of KCN. After the
reaction is complete (in general, after about three hours),
the solution is diluted with water to twice its volume and
precipitated with hydrochloric acid. If desired, the raw
product obtained can be recrystallized, e.g., in a benzene/
cyclohexane mixture. This process is generally usable.
With this process, even thio-oxanilic acid-nitriles are
obtainable, which have not yet been described in the
literature.
The aromatic radical of the thio-oxanilic acid-
nitri~e may be substituted in o-, m-, or p-position, in
single or mu]tiple substitution. Principally, also
condensed aromatic systems, such as, the naphthyl groups,
are considered as aromatic radicals.
~8i
Examples of substituents at the aromatic radical
are saturated or unsaturated alkyl groups of 1-20 C-atoms,
par~icularly the methyl-, ethyl-, propyl-, isopr~pyl-,
butyl-, allyl- and crotyl-groups; also aliphatic radicals
with a hetero-atom, e.g., ether or analogous thio-ether
groups, especially methoxy-, ethoxy-allyloxy-crotyloxy- or
methylmercapto-ethylmercapto-allylmercapto-crotylmercapto-
radicals; the halogen groups (especially chlorides and
bromides); organic and inorganic ester groups, as well as
dialkylamino- and nitro-groups, the nitrile group, etc.
Examples of the compounds of the invention having
the formula
R S
N - C
C C = N - H
~ \ /
0 N
CH3
are:
l-Methyl-3-phenyl-~-thioparabanic acid-5-imide;
1-Methyl-3-p-chlorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-o-chlorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-m-chlorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-o,p-dichlorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-m,p-dichlorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-fluorophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-(p-trifluoromethyl-phenyl)-4-thioparabanic
acid-5-imide;
l-Methyl-3-p-nitrophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-o,p-dinitrophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-methylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-m-methylphenyl-4-thioparabanic acid~5-imide;
l-Methyl-3-o-methylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3~m,p-dimethylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-o,p-dimethylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-o,o,p-trimethylphenyl-4-thioparabanic acid-5-
imide;
l-Methyl-3-p-ethylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-m-ethylphenyl-4-thioparabanic acid-5-imide;
1-Methyl-3-o,p-diethylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-propylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-isopropylphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-methoxyphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-ethoxyphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-propoxyphenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-mercaptomethylphenyl-4-thioparabanic acid-
5-imide;
l-Methyl-3-p-mercaptoethylphenyl-4-thioparabanic acid-5-
imide;
1-Methyl-3-p-mercaptopropylphenyl-4-thioparabanic acid-5-
imide;
l-Methyl-3-p-nitrilophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-m-ni~rilophenyl-4-thioparabanic acid-5-imide;
l-Methyl-3-p-carboxymethyl-phenyl-4-thioparabanic acid-5-
imide;
l-Methyl-3-p-carboxyethyl-phenyl-4-thioparabanic acid-5-
imide;
l-Methy1-3-p-carboxypropyl-phenyl-4-thioparabanic acid-5-
imide;
l-Methyl-3-p-methylsulfonato-phenyl-4-thioparabanic acid-S-
imide;
l-Methyl-3-p-ethylsulfonato-phenyl-~--thioparabanic acid-5-
imide.
The effective compounds according to the invention
may be used alone or in mixture with other substances. In
general, they are used as mixtures with solid or liquid
diluents or as solutions with solid or liquid solvents, the
total content of effective agent being between 0.01 and 95%
by weight.
As a rule, the mixtures or solutions are applied
as emulsion concentrates, pastes, spraying powders,
granulates or micro-capsules.
Emulsion concentrates and pastes contain in
general 10-90% by weight, preferably 15-50% by weight of
effective agent, 2-25% by weight of auxiliary dispersing
agents and organic solvents and/or water.
Spraying powders contain mostly 10-80% by weight ,
preferably 15-70% by weight of effective agent, 1-10% by
weight of auxiliary dispersing agents and 10-89% by weight
of inert components.
Granulates and micro-capsules contain 1-10% by
weight, preferably 5-10% by weight of effective agent, in
addition to inert components, binders and/or coatings.
According to the invention, the following are used:
As dispersing agents, e.g., alkyl- and
aryl-sulfonates, methyl cellulose, polymer sulfonic acids,
~i5~
and their salts, polyalcohols, fatty acid esters, fatty
alcohol ethers, fatty amines;
As organic solvents, e.g., alcohols, such as
ethanol, butanol, dimethyl formamide tDMF), dimethyl
sulfoxide (DMSO), N-methylpyrrolidone aromatics, such as
toluene and xylene;
As inert components, e.g., kaolin, china clay,
talcum, calcium carbonate, highly dispersed silicic acid,
silicic gels, kieselgur, diatomateous earth, pumice, split
brick, crushed corn, thickening agents, such as starch and
carboxymethyl-cellulose; and
As binders, e.g., magnesium sulfate, gypsum, and
gum arabic.
The following formulation may be used as a
herbicide:
1. Emulsion concentrate:
51.4% by weight of effective agent
30 ~/O by weight of Sillitin Z
10 % by weight of highly dispersed silicic acid
(HDK)
6 % by weight of lignin sulfonate (cell pi~ch)
2 % by weight of polypropylene glycol
0.6% by weight of sodiumoleyl-methyltauride.
2. Spraying Powders:
20% by weight of effective agent
44% by weight of china clay
16% by weight of highly dispersed silicic acid
l5% by weight oE lignin sulfonate (cell pitch)
5/O by weight of sodium-alkylnapthalinesulfonate-
formaldehyde condensate (Atlox 4862,
Registered trademark~
In general, the ef~ective compounds are used in
amounts of 0.5-8 kg/ha, preferably 2-4 kg/ha.
The application as herbicide may be carried out
both on the plants (post-emergence method) and on soil free
vegetation (pre-emergence or pre-sowing method). The
greater herbicidal effect is obtained with application to
the soil, preferably before plant cultures have been sown,
with subsequent flat, mechanical workin~ of the herbicides
into the uppermost layers of the soil.
In the fol]owing, a number of examples will
describe both the preparation of the compounds according to
the invention and their herbicidal effects. It should,
however, be understood that the examples are given by way of
illustration and not of limitation.
~ le 1
Preparation of l-methyl-3-phenyl-4-thioparabanic acid-5-
imide (III)
R C6H5
1st Step
20 g of thio-oxanilic acid-nitrile (1) purified by
recrystallization from benzene/cyclohexane (1:1) are
dissolved at 20C in 30 ml freshly distilled, HCl-free
methylisocyanate. When standing overnight, compact, reddish-
- 10 -
~15~
yellow crysta:Ls are deposited. After 24 hours, excess
methylisocyanate is distilled oEE and the resi(lue is
recrystalliæed in benzene. The yield is 25 g (92% of the
theoretical amount) of N-meti-ylcarbamoyl-thio-oxanilic
acid-nitrile (II) having a m.p. of 116C (decomposition).
_nd S_~p
20 g (II) are dissolved in a suffic;ent amount oE
boiling ethanol. Upon cooling, 19 g (95% of the theoretical
amount) of yellow crystals of l-methyl-3-phenyl-
4-thioparabanic acid-5-imlde (III) are obtained, having a
m.p. of 132C.
Exampl _
Preparation of l-methyl-3-phenyl-4-thioparabanic acid-5-
imide (III)
R C6H5
60 g crude, non-recrystalli~ed thio-oxanilic
acid--nitrile (IA) prepared according to the prescription of
A. Reissert and K. Bruggemann appearing in Ber. dtsch. chem.
Ges. 57, 981 (1924) are covered by pouring thereon 90 ml
methylisocyanate at 20C, to which 8 ml HGl gas had been
previously added. After standing for 24 hours, excess
methylisocyanate is distilled off and the residue is
recrystallized in ethanol. In a yield of 55.7 g, the
product (III) as given above, is obtained. M.p. 129-131C.
Comparison Example 1
10 g pure thio-oxanilic acid-nitrile (I) ~analo-
gous to Example 1) are dissolved in 15 ml methylisocyanate,
~ ~5~
to which are added 0.45 ml gaseous HCl. After standing for
24 hours, a black, tarry residue is obtained. It was not
possible to isolate the thioparabanic acid product.
Example 3
-
Preparation of l-methyl.-3-o-chlorophenyl-4-thioparabanic
acid-5-imide (IV)
R = o-ClC6H4
5 g o-chloro-thio-oxanilic acid-nitrile are
covered by pouring thereon 20 ml HCl-free methylisocyanate
and the same ;s allowed to stand 24 hours at 20C.
Subsequently, excess methylisocyanate is dis~;lled o~E and
finally the residue is recrystallized in ethanol. Obtained
are 3.35 g of yellow crystals of (IV), m.p. 129-131C.
Example 4
Preparation of l-methyl-3-o-chlorophenyl-4-thioparabanic
acid-5-imide (IV)
R = o-ClC6H4
Operation is carried out in a manner ana]ogous to
Example 3, with the difference that instead of treating at
20C, the mixture is reacted for 2 hours in boiling
methylisocyanate. The operation leads to the same result as
Example 3.
Example 5
Preparation of l-methyl-3-p-fluorophenyl-4-thioparabanic
acid-5-imide (V)
R = p-F-C6~l
- 12 -
~ ~5~
5 g p-Eluoro-thio-oxanilic acid-nitrile are
reacted with 20 ml methylisocyanate at 20C. The further
process is carried out as in Example 3. Obtained are yellow
crystals of (V) in a yield oE 5.2 g; m.p. l22-124C.
Exampl _
Preparation of l-methyl-3-o-methoxyphenyl-~l-thioparabanic
acid-5-imide (Vl)
o CH30C6H~
38.4 g o-methoxy-thio-oxanilic acid-nitrile are
dissolved in 60 ml pyridine and added thereto are 11.4 g
methylisocyanate. The mixture is allowed to stancl for 24
hours at 20C. Pyridine is subsequently distilled off and
the residue is recrystallized in ethanol. Obtained are 29 g
of (VI) with a m.p. of 124-127C.
Exampl _
Preparation of l-methyl-3-(3,4 dichlorophenyl)-4-thio-
parabanic acid-5-imide (VII)
R = o,p-Cl2C6H3
10 g 3,4-dichloro-thio-oxanilic acid-nitrile are
dissolved in 60 ml pyridine and added thereto are 2.5 g
methylisocyanate. After 24 hours of standing, the pyridine
is distilled off under vacuum, and the residue is dissolved
in a small quantity of hot ethanol. Obtained are 8.1 g of
raw (VII). After renewed recrystallization in 100 ml
ethanol, 5.8 g of yellow crystals (VII) remain; m.p.
135-137C.
- 13 -
Example 8
Preparation of l-methyl-3-para-tolyl-4-thioparabanic acid-5
imide (VIII)
R = p-CH3C6H4
10 g p-methyl-thio-oxanilic acid-nitrile,
dissolved in 20 ml pyridine, are reacted while cooled with
3.25 g methylisocyana~e. After 24 hours at 20C, the
mixture is evaporated and the residue recrystallized in 50
ml ethanol. Obtained are yellow crystals of (VIII) in a
yield of 7.9 g; m.p. 135-137C.
Example 9
Herbicidal effectiveness of l-methyl-3-phenyl-4-thio-
parabanic acid-5-imide (III)
The herbicidal effectiveness of this compound
according to the invention was tested with a single
application in green houses. In the test described, first
the seed grains of the cultured plants and of the weeds were
sown in arable soîl rich in minerals and poor in humus, and
then lightly covered with soil particles. Immediately after
the sowing (and, in any case before germination of the seeds
in the soil), the effective compound according to the
învention was evenly sprayed onto the surface Eree of
vegetation, by means of spraying powders or emulsion
concentrates. Four weeks later, the plants were finally
evaluated as to damage or destruction, while untreated
control plants, which had grown up in the meanwhile, served
as a reference.
- 14 -
5~ 8~
Effectiveness in % with application o-f 0.5-2 kg/ha
of active substance in the pre-emergence process is shown in
the table below.
KG/HA ACTIVE SUBSTA~CE
0.5 1.0 2.0
Useful Plants
Cotton 0 0 10
Sorghum millet 0 0 20
Corn 0 0 10
Lucerne 0 0 lO
Peas 0 10 20
Common beans 10 30 40
Dicotyledonous Weeds
Sinapis arvensis 98 100 100
Chenopodium album 75 95 98
Chrysanthemum segetum 100 100 100
Galinsoga parviflora 85 100 100
Centaurea cyanus 30 75 98
Stellaria media 100 100 100
Polygonum persicaria 75 95 100
Galium aparine 85 95 98
Amaranthus retroflexus 100 lO0 100
Lamium purpureum 75 100 100
Senecio vulgaris 30 75 100
Capsella bursa-pastoris 95 98 100
Matricaria inodora 100 100 100
Weed Grasses
Poa annua 100 100 100
Alopecurus myosuroides 95 98 100
Avena fatua 95 98 100
Digitaria sanguinalis 98 100 100
Echinochloa crus-galli 85 98 100
- 15 -
5~
Example 10
Herbicidal effectiveness of l-methyl-3-p-chlorophenyl-4-
thioparabanic acid-5-imide
The effective agent is tested in an analogous
manner to ~xample 9 in the pre-emergence process.
Effectiveness in % with amounts of 0.5-2 kg/ha
active substance in the pre-emergence process:
KG/HA ACTIVE SUBSTANCE
0.5 1.0 2.0
1 0
Useful Plants
Cotton 0 0 10
Sorghum millet 0 0 0
Corn 0 0 0
Lucerne 0 10 20
Dicotyledonous Weeds
Sinapis arvensis 85 100 100
Chenopodium album 80 95 100
Chrysanthemum segetum 95 100 1.00
Galinsoga parviflora 98 100 100
Centaurea cyanus 70 85 100
Stellaria media 90 98 100
Amaranthus retroflexus 60 100 100
Capsella bursa-pastoris 100 100 100
Matricaria inodora 98 100 100
Solanum nigrum 80 98 100
Viola tricolor 85 98 100
- 1~ -
5~l18~
KG / HA ACT I VE SUB STANCE
0.5 1.0 2.0
Weed Grasses
Poa annua 95 100 100
Alopecurus myosuroides85 95 100
Avena fatua 50 95 100
Setaria viridis 70 100 100
Apera spica-venti 100 100 100
Example 11
Herbicidal effectiveness of l-methyl-3-(3',4'-dichloro-
phenyl)-4-thioparabanic acid-5-imide
The ef~ective agent is tested in an analagous
manner to Example 9 in the pre-emergence process.
Effectiveness in % with amounts at 1-4 kg/ha
active substance:
KG/HA ACTIVE SUBSTA~CE
1.0 2.0 4.0
20 Useful Plants
_ _
Sorghum-millet 0 0 0
Corn 0 0 0
Lucerne 0 0 10
Summer barley 0 0 10
Dicotyledonous Weeds
Chenopodium album 100 100 100
Chrysanthemum segetum 98 100 100
Galinsoga parviflora 98 100 100
Stellaria media 90 100 100
Amaranthus retroflexus 60 100 100
- 17 -
~s~
KG/HA ACTIVE SUBSTANCE
1.0 2.0 4.0
Capsella bursa-pastoris 100 100 100
Matricaria inodora 90 100 100
Solanum nigrum 100 100 100
Viola tricolor 75 100 100
Weed Grasses
Poa annua 98 100 100
Setaria viridis 85 95 100
Apera spica-venti 95 100 100
Comparison Example 2
For purposes of comparison, a commercial herbicide
of the urea group, e.g, Afalon with the effective agent
Linuron [3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-
urea] was tested. Otherwise, the procedure was the same as
followed in Example 9.
Effectiveness in % when applying from 0.5-2.0 kg/ha
active substance in the pre-emergence process:
LINURON (AFALON)
KG/HA ACTIVE SUBSTANCE
0.5 1.0 2.0
Useful Plants
Winter-wheat O 10 50
Cotton O 0 10
Sorghum-millet 0 20 70
Corn O 10 40
Lucerne 95 100 100
Peas 0 40 70
Common beans 10 70 100
- 18 ~
~S~
NURON (AFALON)
KG/HA ACTI~lE SUBSTANCE
0.5 1.0 2.0
Dicotyledonous Weeds
Sinapis arvensis 98 100 100
Ghenopodium album 70 95 98
Chrysanthemum segetum 85 98 100
Galinsoga parviflora 98 100 100
10 Centaurea cyanus 0 3U 70
Stellaria med ia 100 100 100
Polygonum persicaria 50 95 100
Galium aparine 35 45 50
Amaranthus retroflexus 100 100 100
Lamium purpureurn 90 98 100
Senecio vulgaris 30 80 98
Capsella bursa-pastoris 98 98 100
Matricaria inodora 95 100 100
Weed Grasses
Poa annua 70 80 95
Alopecurus myosuroides 60 70 85
Avena fatua 40 50 80
Digitaria sanguinalis 70 80 95
Echinochloa crus-galli 80 95 100
The comparison of the results of Examples 9, 10
and 11 with Comparison Example 2, shows the improved
compatibility with useful plants of the act-ive agents
according to the invention, especially in the group of the
fami].y leguminosae, a.s compared to the standard herbicide.
The herbicide superiority is also remarkable especia]ly
against weed grasses and cleavers, where the compounds
according to the invention are of exceedingly high activity.
_ 19 _
Comparison Example 3
In a further test series, comparison was made with
the commercial product Lasso having an active agent Alachlor
[2'-chloro-2,6-diethyl-N-(methoxymethyl)-acetanilide].
Otherwise, the procedure was the same as followed in Example
9.
Effectiveness in % with application of 0.5-2 kg/ha
of active substance in the pre-emergence process:
LASSO (ALACHLOR)
KG/HA ACTIVE SUBSTANCE
0.5 1.0 2.0
Useful Plants
Corn 0 10 30 ':
Sorghum-millet 85 98 100
Dicotyledonous Weeds . :
Stellaria media 40 60 75
Galium aparine 0 10 20
Centaurea cyanus 0 20 40
Chrysanthemum segetum 0 30 70
Senecio vulgaris 20 40 75
Raphanus raphanistrum 0 10 20
Weed Grasses
Avena fatua 60 70 85
Alopecurus myosuroides 50 6~ 98
Comparison of the results of Examples 9, 10 and 11
with Comparison Example 3 show a considerably improved
effectiveness of the compounds according to the invention,
particularly in combating the dicotyledonous plants with
comparable tolerance to corn and even decisively improved
compatibility with sorghum-millet.
- 20 -
Example 12
Herbicidal effectiveness of l-methyl~3-p-chlorophenyl-4-
thioparabanic acid 5-imide
The possibilities of application of the compound
according to the invention in the post-emergence process
(application to the leaves of the plants) were tested in a
further test series in the greenhouse. In this process, the
effective agent was sprayed onto the plants which had
reached a certain growth: in dicotyledonous plants in
addition to the primary cotyledons, the first, genuine pair
of leaves was developed; and in monocotyledonous plants, at
least two leaves were formed.
The treated plants were evaluated for the last
time after 1~ days of spraying for damage and destruction.
Herbicidal effectiveness in % at 1.2 and 4 kg/ha
application of active substance in the post-emergence
process:
KG/HA ACTIVE SUBSTANCE
1 2 4
2Q
Useful Plants
Summer Barley 0 0 20
Corn o o Q
Sorghum-millet 0 0 20
Lucerne Q lQ 20
Dicotyledonous Weeds
Stellaria media 75 9~ 100
Chrysanthemum segetum 50 95 lQQ
Galinsoga pa-rviflora 60 98 lQ0
- 21 -
5~
KG/HA ACTIVE SUBSTANCE
1 2 4
Senecio vulgaris . 50 70 98
Capsella bursa-pastoris 95 100 100
Chenopodium album 90 98 100
Solanum nigrum 75 90 100
Polygonum persicaria 60 85 98
Weed Grasses
Poa annua 70 98 100
Apera spica-venti 70 95 100
Example 13
Herbicidal effectiveness of l-methyl-3-(3',4'-dichloro-
phenyl)-4-thioparabanic acid-5-imide in the post-emergence
process
The effective agent is tested in an analogous
manner to Example 12 in the post-emergence process.
Herbicidal effectiveness in % with application of
0.5-2 kg/ha of active substance in the post-emergence
process:
KG/HA ACTIVE SUBSTANCE
0.5 1 2
-
Useful Plants
Summer Barley 0 0 0
Corn 0 0 0
Sorghum-millet 0 0 0
Lucerne 0 0 20
5~
K(,/}IA ACT[VLI, SUBSTANC~
0.5 l 2
Dicotyledonou~s Weec]s
. . .
Stellaria media 80 95 100
Chrysanthemum segetum 90 98 100
Galin~oga parvif.Lora 85 90 98
Centaurea cyanus 60 95 98
Capsella bursa-pastoris 95 :L00 100
Chenopodium alburn 98 100 100
Solanum nigrum 75 80 100
Polygonum persicaria 95 98 100
Amaranthus retroflexus 95 100 100
Galium aparine 70 85 95
Thus, while only several examples of the present
invention have been shown and describecl, it will be obvious
that many changes and modi~ications may be made thereunto,
without departing from the spirit and scope of the invention.
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