Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
~IL24~S3~
Case 5-14639/+
HERBICIDAL COMPOSITIONS
The invention relates to a selectively acting
composition which contains as herbicidal active ingredient
a sulfonylurea, together with a known antagonistically
acting substance (antidote), selected from the group
comprising cyanobenzacetonitrile, N,N-diallyl-dichloro-
acetamide, 2-chloro-5-benzyloxycarbonyl-3-trifluoromethyl-
triazole, 1,8-naphthalenecarboxylic acid anhydride and
3-N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine, which
increases the tolerance of the cultivated plants to the
phytotoxic action, without as a result the herbicidal
effectiveness against the weeds being noticeably reduced.
The invention relates also to the use of this composition
for controlling weeds in crops of useful plants.
Sulfonylureas having herbicidal activity are known,
cf. for example the U.S. Patent Specifications Nos. 4,127,405,
4,169,719 and 4,238,628, and the published European
Patent Applications Nos. EP-A 44 807, 99 339 and 108 708.
Compared with other herbicides, these sulfonylureas
are distinguished b~ their strong action. From an
ecological and economic viewpoint, the use of small amounts
of active substance is advantageous. There is however
involved the risk of a harmful overdosage resulting; but
,, .
1240531
damaging effects are attributable not only to a possible
overdosage but in some cases also to abnormal climatic
conditions or to the preliminary treatment of the soil.
It has ?roved therefore to be desirable to increase the
resistance or tolerance of the cultivated plants to the
phytotoxic action of the sulfonylurea herbicides. In the
U.S. Patent Specification No. 4,343,649, it is described
that the known herbicide antidotes 1.8-naphthalenic acid
anhydride, N,N-diallyldichloroacetamide and a-cyano-
methoximino-2-phenylacetonitrile meet this requirement
when they are used in cultivated crops simultaneously with
the sulfonylurea herbicide.
It has now been found that, surprisingly, the resistance
of cultivated plants to the phytotoxic action of sulfonyl-
urea herbicides is increased, without as a result the
herbicidal action on the majority of weeds and wild grasses
being impaired, when the sulfonylurea herbicides are used
together with oxime ethers acting as herbicidal antagonists
or antidotes.
The sulfonylurea herbicides correspond to the general
formula I
Q-S02-NH-CO-NH-T (I)
wherein Q is a substituted phenyl group of the formula
/Y
/ \
X/
in which X is Cl-C3-haloalkenyl, Cl-C3-alkoxycarbonyl,
C3-C4-alkenyloxy, Cl-C3-haloalkoxy, Cl-C3-alkoxy-Cl-C2-
alkoxy or nitro, Y is hydrogen or halogen, or Q is the
3-methyl-3,4-dihydro-1,2-benzoxathiin-8-yl radical, and
,~
~240531
-- 3 --
T is a substituted, six-membered, heterocyclic radicai
of the formula
~N_$
-C\N
~2
wherein E is -CHz or -N=, Rl is Cl~C3-alkyl, Cl-C3-alkoxy,
Cl-C3-haloalkoxy or cyclopropyl, and R2 is Cl-C3-alkyl,
Cl-C3-alkoxy, Cl-C3-haloalkoxy or cyclopropyl, with the
proviso that Rl and R2 cannot simultaneously be methyl
when X is methoxycarbonyl and Y is hydrogen.
Compounds in which Y is hydrogen are preferred.
- Halogen can be for example fluorine, chlorine and bromine,
particularly chlorine.
- By haloalkenyl is meant for example haloethanyl, halo-
propenyl and, preferably, 3,3,3-trifluoropropenyl.
- Alkoxycarbonyl can be for example methoxy, ethoxy, propoxy
or isopropoxycarbonyl, but preferably methoxycarbonyl.
- By alkenyloxy is meant for example: allyloxy, propenyloxy,
buten-2-yloxy, buten-3-yloxy, l-methyl-alkyloxy, 2-methyl-
alkyloxy, l-methylpropenyloxy and 3-methylpropenyloxy,
especially however allyloxy and buten-2-yloxy.
- Haloalkoxy can be for example: halomethoxy, haloethoxy,
halopropoxy and haloisopropoxy, preferably however
chloromethoxy, chloroethoxy, fluoromethoxy, fluoroethoxy;
particularly preferred as X is 2 chloroethoxy and
pentafluoroethoxy, and a~ Rl difluoromethoxy.
- By alkoxy-alkoxy is meant for example: methoxy-methoxy,
2-methoxy-ethoxy, ethoxy-methoxy, 2-ethoxy-ethoxy,
n-propoxy-methoxy, isopropoxy-methoxy, 2-n-propoxy-ethoxy
~24(~531
-- 4 --
and 2-isopropoxy-ethoxy, but especially 2-methoxy-ethoxy.
- Y can be for example hydrogen or halogen, such as fluorine,
chlorine or bromine, in particular hydrogen or chlorine.
- By alkyl is meant for example: methyl, ethyl, n-propyl
or i-propyl, preferably methylO
- Alkoxy is for example: methoxy, ethoxy, n-propoxy or
i-propoxy, preferably methoxy and ethoxy.
Sulfonylureas which have proved particularly effective
herbicidally are the compounds of the formula I wherein
Y is H.
The following sulfonylureas are especially preferred
herbicides:
N-[2-(2'-chloroethoxy)-phenyl-sulfonyl~-N'-(4-methyl-6-
methoxy-triazin-2-yl)-urea, N-[2-(2'-methoxyethoxy)-phenyl-
sulfonyl]-N'-(4-methyl-6-methoxy-triazin-2-yl) urea,
N-12-(2-bute~yloxy)-phenyl-sulfonyl~-N'-(4-methyl-6-methoxy-
triazin-2-yl)-urea, N-[2-(3-trifluoropropen-l-yl)-phenyl-
sulfonyl]-N'-~4-methyl-6-methoxy-triazin-2-yl)-urea,
N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methyl-6-difluoro-
methoxypyrimidin-2-yl)-urea, N-(2-methoxycarbonylphenyl-
sulfonyl)-N'-(4-methyl-6-difluoromethoxypyrimidin-2-yl)-urea,
N-(2-pentafluoroethoxyphenyl-sulfonyl)-N'-(4,6-dimethoxy-
triazin-2-yl)-urea, N-(2-allyloxyphenyl-sulfonyl)-N'-
(4-methyl-6-ethoxy-triazin-2-yl)-urea, N-(2-nitrophenyl-
sulfonyl)-N'-(4-methyl-6-difluoromethoxy-pyrimidin-2-yl)-
urea, N-(2-methoxycarbonyl-phenyl-sulfonyl)-N'-(4-methyl-6-
cyclopropyl-pyrimidin-2-yl)-urea and N-(3-methyl-3,4-
dihydro-l,2-benzoxathiin-8-yl-sulfonyl~-N'-(4-methoxy-6-
methyl-pyrimidin-2-yl)-urea.
lZ40531
-- 5 --
As an antidote to counteract these sulfonylureas
there is used any one of the following compounds:
a) cyanomethoximino-benzacetontr-lle of the formula
C;~CN (II)
N-0-CH ;, CN
known from the German Offenlegungsschrift No. 2,639,405;
b) N,N-diallyl-dichloroacetamide of the formula
(cH2=cH-cH2)2N-cocHcl2 (III),
known from the German Offenlegungsschrift No. 2,218,074;
c) 2-chloro-5-benzyloxycarbonyl-3-trifluoromethyl-triazole
of the formula
CF3-~ - ~-COOCH2--\ /- (IV),
! Cl
known from the U.S. Patent Specification No. 4,199,506;
d) 1,8-naphthalenedicarboxylic acid anhydride of the formula
\-./ \o (V~,
-co
known from the German Offenlegungsschrift No. 1,567,075; and
e) 3-N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine of the
formula
0531
CO-CHC 1 2
(VI),
3 3
known from the German Offenlegungsschrift No. 2,218,079
known from the European Patent Application No. 110~7.
The compounds of the formulae II to VI are used
according to the invention as antidotes to counteract the
effects of sulfonylureas of the formula I.
These compounds have been described as safeners or
antidotes for herbicides having a structure other than
the sulfonylurea structure. Such herbicides are applied
in largish amounts. It has now been shown that,
surprisingly, the said compounds are capable of antagonising,
in specific cultivated crops, also the class of these novel
sulfonylureas of the formula I, which have a very strong
action.
The compounds of the formulae II to VI are suitable
for protecting cultivated plants against the harmful action
of sulfonylureas, and can therefore be described, with
regard to their application in combination with the
aforementioned herbicides, as preventives or antidotes
and also as safeners.
Depending on the purpose of application, such a
preventive or antidote can be used for the pretreatment of
the seed or seedlings of the cultivated plants (dressing
of the seed or of the cuttings), or can be introduced into
the soil before or after sowing. It can however be applied
on its own or together with the herbicide before or after
the emergence of the plants. The treatment of the plant
~LZ4C~531 `
-- 7 --
or of the seed or seedlings with the antidote can be
carried out therefore essentially independently of the
time of application of the phytotoxic chemicals. The
treatment of the plants can however be effected by the
sumultaneous application of phytotoxic chemicals and
antidote (tank mixture). The pre-emergence treatment
includes both the treatment of the cultivated area before
sowing (ppi = pre plant incorporation) and the treatment
of the sown cultivated area before emergence of the plants.
The applied amounts of antidote in proportion to the
amount of herbicide depend largely on the mode of
application. In the case of field treatment, where the
herbicide and antidote are applied either simultaneously
(tank mixture) or separately, the ratio of the amounts of
antidote to herbicide is within the range of 1:10 to 10:1.
The full protective action is however obtained as a rule
with a ratio of antidote to herbicide of 1:3 to 3:1.
Which ratio is most suitable with regard to the optimum
effect with a specific cultivated plant is determined from
case to case, that is to say, depending on the type of
herbicide to be used. With seed dressing and similar
specific protective measures, however, the amounts of
antidote required compared with the amounts of herbicide
applied later per hectare of cultivated land are much
smaller. There are generally needed for seed dressing
0.1 to 50 g of antidote per kg of seed. As a rule, the
maximum protective effect is obtained with amounts as low
as 0.5 to4 g of antidote per kg of seed. When the
antidote is to be applied shortly before sowing, by seed
soaking, there are advantageously employed antidote
solutions containing the active ingredient at a concen-
tration of 1 - 10,000 ppm. rhe full protective action is
~Zg~531
as a rule obtained with a concentration of antidote of
10 - 1000 ppm.
Protective measures, such as seed dressing and treatment
of cuttings with an antidote of the formulae II-VI, and
eventual subsequent field treatment with agricultural
chemicals are as a rule separated by a considerably
interval of time. Pretreated seed and plant material
can later come into contact, in agriculture, horticulture
and foresty, with various chemicals. The present invention
relates therefore also to protective compositions for
cultivated plants, which compositions contain as active
ingredient an antidote of the formulae II-VI, together with
customary carrier materials. These preparations can if
required additionally contain those agricultural chemicals
against which the cultivated plant is to be protected.
Cultivated plants applying within the scope of the
present invention are all those which in some form produce
productive materials, such as seeds, roots, stalks, tubers,
leaves and flowers, or components such as oils, sugar, starch,
protein, and so forth, and which for this purpose are
cultivated and preserved. These plants include for example
varieties of cereals, such as wheat, rye, barley and oats,
in addition particularly rice, sorghum, maize, cotton, sugar
beet, sugar cane, soybean, beans and peas.
The antidote o the invention can be used in all cases
where a cultivated plant of the aforementioned varieties
has to be protected against the harmful action of
sulfonylureas of the formula I.
For the dressing of the seed of the cultivated plant,
the seeds are thoroughly mixed in the desired ratio with
the antidote of the formulae II to VI.
12~VS31
For application, the compounds of the formula I and
II-VI are used either in an unmodified form or preferably
together with auxiliaries customarily employed in
formulation practice, and are thus processed in a known
manner for example into the form of emulsion concentrates,
directly sprayable and dilutable solutions, diluted
emulsions, wettable powders, soluble powders, dusts or
granulates, and also encapsulations in for example poly-
meric substances. The application processes, such as
spraying, atomising, dusting, scattering or pouring, and
likewise the type of composition, are selected to suit
the objectives to be achieved and the given conditions.
The formulations, that is ~o say, the compositions
or preparations containing the active ingredients of the
formulae I and II to VI and optionally a solid or liquid
additive, are produced in a known manner, for example by the
intimate mixing and/or grinding of the active ingredients
with extenders, such as with solvents, solid carriers and
optionally surface-active compounds (tensides).
Suitable solvents are: aromatic hydrocarbons, prefer-
ably the fractions C8 to C12, such as xylene mixtures or
substituted naphthalenes, phthalic esters, such as dibutyl-
or dioctylphthalate, aliphatic hydrocarbons, such as
cyclohexane or paraffins, alcohols and glycols, as well as
ethers and esters thereof, such as ethanol, ethylene glycol,
ethylene glycol monomethyl or -ethyl ethers, ketones,
such as cyclohexanone, strongly polar solvents, such
as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl-
formamide, as well as optionally epoxidised vegetable oils,
such as epoxidised coconut oil or soybean oil:, or water.
The so]id carriers used, for example for dusts and
dispersible powders, are as a rule natural mineral
~Z4~531
- 10 -
fillers, such as calcite, talcum, kaolin, montmorillonite
or attapulgite. In order to improve the physical
properties, it is also possible to add highly dispersed
silicic acid or highly dispersed absorbent polymers.
Suitable granulated adsorptive carriers are porous types,
for example pumice, ground brick, sepiolite or bentonite;
and suitable nonsorbent carriers are materials such as
calcite or sand. There can also be used a great number
of pre-granulated materials of inorganic or organic
nature, such as in particular dolomite or ground plant
residues.
Suitable surface-active compounds are, depending on the
nature of the active ingredients of the formulae I and II-VI
to be formulated, nonionic, cationic and/or anionic tensides
having good emulsifying, dispersing and wetting properties.
By 'tensides' are also meant mixtures of tensides.
Suitable anionic tensides are both so-called water-
soluble soaps and water-soluble, synthetic, surface-
active compounds.
Soaps which are applicable are for example the alkali
metal, alkaline-earth metal or optionally substituted
ammonium salts of higher fatty acids (C10-C22), such as the
Na or K salts of oleic or stearic acid, or of natural
fatty acid~mixtures, which can be obtained for example
from coconut oil or tallow oil. Also to be mentioned are
the fatty acid-methyltaurine salts.
So-called synthetic tensides are however more
frequently used, particularly fatty sulfonates, fatty
sulfates, sulfonated benzimidazole derivates or
alkylarylsulfonates.
The fatty sulfonates or sulfates are as a rule in the
:lZ4V531
form of alkali metal, alkaline-earth metal or optionally
substituted ammonium salts, and contain an alkyl group
having 8 to 22 C atoms, 'alkyl' including also the alkyl
moiety of acyl groups, for example the Na or Ca salt of
ligninsulfonic acid, of dodecylsulfuric acid ester or of a
fatty alcohol sulfate mixture produced from natural
fatty acids. Included among these are the salts of
sulfuric acid esters and sulfonic acids of fatty alcohol
ethylene oxide adducts. The sulfonated benzimidazole
derivatives preferably contain 2 sulfonic acid groups
and a fatty acid group having 8 - 22 C atoms. Alkylaryl-
sulfonates are for example the Na, Ca or triethanolamine
salts of dodecylbenzenesulfonic acid, of dibutylnaphthalene-
sulfonic acid or of a naphthalenesulfonic acid-formaldehyde
condensation product.
Also suitable are corresponding phosphates, for example
salts of the phosphoric ester of a p-nonylphenol-(4-14)-
ethylene oxide adduct, or phospholipides.
Suitable nonionic tensides are in particular polyglycol
ether derivatives of aliphatic or cycloaliphatic alcohols,
saturated or unsaturated fatty acids and alkylphenols,
which can contain 3 to 30 glycol ether groups and 8 to 20
carbon atoms in the (aliphatic) hydrocarbon radical and
6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
Further suitable nonionic tensides are the water-
soluble polyethylene oxide adducts, which contain 20 to
250 ethylene glycol ether groups and 10 to 100 propylene
glycol ether groups, with polypropylene glycol, ethylene-
diaminopolypropylene glycol and alkylpolypropylene glycol
having 1 to 10 carbon atoms in the alkyl chain. The
compounds mentioned usually contain 1 to 5 ethylene
glycol units per propylene glycol unit.
1~4V53~
- 12 -
Examples of nonionic tensides which may be mentioned
are: nonylphenolpolyethoxyethanol, castor oil polyglycol
ethers, polypropylene/polyethyleneoxy adducts, tributyl-
phenoxypolyethoxyethanol, polyethylene glycol and octyl-
phenoxypolyethoxyethanol.
Suitable also are fatty acid esters of polyoxyethylene-
sorbitan, such as polyoxyethylenesorbitan-trioleate.
In the case of the cationic tensides, they are in
particular quaternary ammonium salts which contain as
N-substituents at least one alkyl group having 8 to 22
C atoms and, as further substitùents, lower, optionally
halogenated alkyl, benzyl or lower hydroxyalkyl groups.
The salts are preferably in the form of halides, methyl
sulfates or ethyl sulfates, for example stearyltrimethyl
ammonium chloride or benzyldi(2-chloroethyl)ethylammonium
bromide.
The tensides customarily used in formulation practice
are described, inter alia, in the following publications:
"Mc Cutcheon's Detergents and Emulsifiers knnual",
MC Publishing Corp., Ridgewood, New Jersey, 1979;
M. and J. Ash, "Encyclopedia of Surfactants", Vol.I-III,
Chemical Publishing Co. Inc. New York 1981-1982; and
H. Stache, "Tensid Taschenbuch", 2nd Edition, C. Hanser
Verlag, Munich and Vienna, 1981.
These preparations contain as a rule: 0.1 to 99%,
particularly 0.1 to 95%, of active ingredient of the
formula I, 1 to 99% of a solid or liquid additive, and
O to 25%, especially 0.1 to 25%, of a tenside.
Whereas commercial products are preferably in the form
of concentrated compositions, the preparations employed
12a~V531
by the end-user are as a rule diluted. The applied forms
can be diluted down to 0.001% of active ingredient. The
amounts applied are as a rule 0.1 to 10 kg of active
ingredient (a.i.) per hectare, preferably 0.25 to 5 kg of
active ingredient per hectare.
The compositions can also contain further additives,
such as stabilisers, antifoaming agents, viscosity
regulators, binders and adhesives, as well as fertilisers,
or other active ingredients for obtaining special effects.
The active ingredients of the formulae I and II to VI
can be produced by known methods.
Compounds of the formula I are produced in an inert
organic solvent.
One process for obtaining the compounds of the formula I
comprises reacting a phenylsulfonamide of the formula (a)
\ ~ \ / 2 NH2
! i! (a),
wherein X and Y have the meanings defined under the formula I,
in the presence of a base, with an N-pyrimidinyl- or
N-triazinylcarbamate of the formula (b)
O ~R
O--C--NH--~ ~E (b)
wherein E, Rl and R2 have the meanings defined under the
formula I.
~Z~0531
- 14 -
A second process for producing compounds of the
formula I comprises reacting a phenylsulfonylisocyanate
of the formula (c)
--SO --N=C=O
\X (c),
wherein X and Y have the meanings defined under the formula
I, optionally in the presence of a base, with an amine of
the formula (d)
H2N ~N ~
~ (d)
wherein E, Rl and R2 have the meanings defined under the
formula I.
Compounds of the formula I are produced using a further
process by reacting a sulfonamide of the formula III given
above, optionally in the presence of a base, with an
isocyanate or isothiocyanate of the formula (e)
N / 1
\N ~ (e)
wherein E, Rl and R2 have the meanings defined in the
formula I.
Finally, the compounds of the formula I can be obtained
also by reacting an N-phenylsulfonylcarbamate of the
formula (f)
lZ40S31
- 15 -
\-~ \1l--S2--NH--C O ~ ~ (
wherein X and Y have the meanings defined under the
formula I, with an amine of the formula (d) given above.
The resulting ureas of the formula I can, if desired,
be converted by means of amines, alkali metal hydroxides
or alkaline-earth metal hydroxides or quaternary ammonium
bases into basic addition salts. This is effected for
example by reaction with the equimolar amount of base
and removal of the solvent by evaporation.
The starting materials of the formulae (a), (c) and (e)
can be produced by the following methods:
The sulfonamides of the formula (a) used as inter-
mediates are obtained from the corresponding anilines by
diazotisation and exchange of the diazo group for sulfur
dioxide in the presence of a catalyst, such as copper-(I)
chloride, in hydrochloric acid or acetic acid, and reaction
of the formed phenylsulfonyl chloride with an ammonium
hydroxide solution.
The compounds of the formula (a) can be obtained also
by oxygen-alkylation or -alkenylation of hydroxyphenyl-
sulfonamides with the corresponding halides or sulfuric
acid esters.
The alkoxyphenylsulfonamides for their part can be
obtained from the corresponding alkoxyanilides, as already
mentioned, or by chlorosulfonylation of alkoxybenzenes,
and reaction of the resulting phenylsulfonyl chlorides
with an ammonium hydroxide solution. Such reactions are
known from J. Am. Chem. Soc. 62, 603 (1940).
~Z4i~)53~
- 16 -
The phenylsulfonylisocyanates of the formula (c) can be
obtained by reactions of the sulfonamides of the formula (a)
with phosgene in the presence of butylisocyanate, in a
chlorinated hydrocarbon as solvent, at the reflux tempera-
ture. Similar methods of preparation are described in
"Newer Methods of Preparative Organic Chemistry", Vol. VI,
223-241, Academic Press, New York and London.
The N-phenylsulfonylcarbamates of the formula (b) are
obtained by reaction of the sulfonamides of the formula (a)
with diphenylcarbamate in the presence of a base. Similar
processes are mentioned in the Japanese Patent Specifi-
cation No. 61 169.
The starting materials of the formulae ~b), (d) an~ (e)
are known or can be produced by known methods.
Isocyanates of the formula (e) can be produced by
reaction of amines of the formula (d) with oxalyl chloride
in a chlorinated hydrocarbon as solvent. Amines of the
formula (d) are known and some are obtainable commercially,
or they can be produced by known methods: cf. "The Chemistry
of Heterocyclic Compounds", Vol. XIV, Interscience
Publishers, New York, London.
These reactions to compounds of the formula I are
advantageously performed in aprotic, inert organic
solvents, such as methylene chloride, tetrahydrofuran,
acetonitrile, dioxane and toluene.
The reaction temperatures are preferably between -20
and ~120C. The reactions in general proceed slightly
exothermically, and can be carried out at room temperature.
For shortening the reaction time or for initiating the
reaction, i~ is advantageous to apply heat for a short
period up to the boiling point of the reaction mixture.
~Z40531
- 17 -
The reaction times can be shortened also by the addition
of a few drops of a base or of an isocyanate as a reaction
catalyst.
The final products can be isolated by means of
concentration by evaporation and/or removal of the solvent
by evaporation, and can be purified by recrystallisation
or trituration of the solid residue in solvents in which
they do not readily dissolve, such as ethers, aromatic
hydrocarbons or chlorinated hydrocarbons.
The compounds of the formulae II-VI are known. The
production thereof can be learnt from the following
publications: German Offenlegungsschriften Nos. 1,567,075,
2,218,079 and 2,639,405, and U.S. Patent Specification
No. 4,199,506~
The following sulfonylureas are tested as herbicides
in the subsequent Examples:
~CH3
A ~ so2NH-coN~-a~ ~ m.p. 174-175C
=-\ N=-
2 4 \OCH3
N-(2-~-chloroethoxyphenylsulfonyl~-N'-(4-methoxy-6-methyl-
triazin-2-yl) urea;
B
OCH2CH=CH2 OC2H5
N-(2-allyloxyphenylsulfonyl)-N'-(4-ethoxy-6-methyl-triazin-
2-yl) urea;
~Z40~3~
- 18 -
C ~ so NH-CONH--~ ~ m.p. 134-138 C
C2H4cH3 OCH3
N-(2-methoxyethoxyphenylsulfonyl)-N'-(4-methoxy-6-methyl-
triazin-2-yl) urea;
D ~ so NH-CON~ m.p. 163-164~
COOCH3 OCHF2
N-(2-methylbenzoylsulfonyl)-N'-(4-difluoromethoxy-6-methyl)-
pyrimidin-2-yl) urea;
~CH3
E ~ -SO2NH-CONH--~ ~N m.p. 159-160C
CH=CHCF3 \OCH3
N-(2-~-trifluoro-propyl-1-enylphenylsulfonyl)-N'-(4-
methoxy-6-methyltriazin-2-yl) urea;
lZ40531
~S02NHCoNH-.~ ~ m.p. 173-175C
COOCH3 \OCH3
N-(2-methoxycarbonyl-phenylsulfonyl)-N'-(4-cyclopropyl-6-
methoxy-2-yl) urea; and
C~3
G /~Z-\ ~=i m.p. 216-218C
\t-S~ OCH3
CH3
N-(3-methyl-3,4-dihydro-1,2-benzoxathiin-8-yl-sulfonyl)-
N'-(4-methoxy-6-methyl- wrimidin-2-yl) urea.
~Z~()531
- 20 -
Formulation Examples for active in~redients of the
formulae II-VI or for mixtures thereof with herbicides
of the formula I
a) Wettable powders a) b) c)
active ingredient of the formulae II-VI 20% 60% 0.5%
or mixture thereof with a herbicide of
the formula I
sodium lignin sulfonate 5% 5% 5%
sodium lauryl sulfate 3%
sodium diisobutylnaphthalene sulfonate - 6% 6%
octylphenolpolyethylene glycol ether - 2% 2%
(7-8 mols of ethylene oxide)
highly dispersed silicic acid 5% 27% 27%
kaolin 67%
sodium chloride - - 59.5%
The active ingredient is well mixed with the additives
and the mixture is thoroughly ground in a suitable mill.
Wettable powders which can be diluted with water to give
suspensions of the required concentration are obtained.
b) Emulsion concentrates a) b)
active ingredient of the formulae II-VI 10% 1%
or mixture thereof with a herbicide of
the formula I
octylphenolpolyethylene glycol ether 3% 3%
(4-5 mols of ethylene oxide)
calcium dodecylbenzene sulfonate 3% 3%
castor oil polyglycol ether 4% 4%
(36 mols of ethylene oxide)
cyclohexanone 30% 10%
xylene mixture 50% 79%
Emulsions of any desired concentration can be obtained
from these concentrates by dilution with water.
~;240531
- 21 -
c? Dusts a) b)
active ingredient of the formulae II-VI 0.1% 1%
or mixture thereof with a herbicide of
the formula I
talcum 99-9%
kaolin ~ 99%
Dusts ready for use are obtained by mixing the active
ingredient with the carriers and grinding the mixture in
a suitable mill.
d) Extruder ~ranulates a) b)
active ingredient of the formulae II-VI L0% 1%
or mixture thereof with a herbicide of
the formula I
sodium lignin sulfonate 2% 2%
carboxymethylcellulose 1% 1%
kaolin 87% 96%
The active ingredient is mixed and ground with the
additives, and the mixture is moistened with water. This
mixture is extruded and then dried in a stream of air.
e) Coated ~ranulate
active ingredient of the formulae II-VI 3%
or mixture thereof with a herbicide of
the formula I
polyethylene glycol (M.W. 200) 3%
kaolin 94%
The finely ground active ingredient is evenly applied,
in a mixer, to the kaolin moistened with polyethylene glycol.
Dustfree coated granules are obtained in this manner.
~LZ40531
- 22 -
f) Suspension concentrates a) b)
active ingredient of the formulae II-VI 40% 5%
or mixture thereof with a herbicide of
the formula I
ethylene glycol 10% 10%
nonylphenolpolyethylene glycol ether 6% 1%
(15 mols of ethylene oxide)
sodium lignin sulfonate 10% 5%
carboxymethylcellulose 1% 1%
37% aqueous formaldehyde solution 0.2% 0.2%
silicone oil in the form of a 75% 0.8% 0.8%
aqueous emulsion
water 32% 77%
The finely ground active ingredient is intimately mixed
with the additives. There is thus obtained a suspension
concentrate from which can be produced, by dilution with
water, suspensions of the concentration required.
~) Salt solution
active ingredient of the formulae II-VI 5%
or mixture thereof with a herbicide of
the formula I
isopropylamine 1%
octylphenolpolyethylene glycol ether 3%
(78 mols of ethylene ox.de)
water 91%
Biolo~ical Examples
The capability of the compounds of the formulae II-VI to
protect cultivated plants against the phytotoxic action
of strong herbicides can be seen from the following
Examples. In the test descriptions, the compounds of the
formulae II-VI are designated as antidotes.
lZ~0531
Example 1: Seed dressin~ with antidote: herbicide in the
pre emer~ence process on maize
Maize seeds of the "LG 5" variety are mixed in a glass
container with the substance to be tested as antidote.
Seeds and product are well mixed together by shaking and
rotation. Plastic pots (upper diameter 11 cm) are filled
with soil, and the dressed seeds are sown therein. After
the seeds have been covered, the herbicide is applied,
The protective action of the antidote is estimated in pPr
cent 21 days after application of the herbicide. The plants
treated with the herbicide alone (no protective action)
and the completely untreated plants (100% growth)
provide reference values.
The results are summarised below:
Herbicide Antidote Relative
No. Applied amount No.Applied amount protective
A125 g/ha II2 g~kg of seed 12.5%
A125 g/ha II1 g/kg of seed 12.5%
A62 g/ha II2 g/kg of seed 25,~
A~2 g/ha II1 g/kg of seed 25,~
A62 g/ha II0.5 g/kg of seed 12.5~
A125 g/ha III 1 g/kg of seed 12.5%
A125 g/ha III 0.5 g/kg of seed 38,~
A125 g/ha III 0.25 g/kg of seed 23~
A62 g/ha III 0.25 g/kg of seed 23,2'
. A125 g/ha V 1 g/kg of seed 38,~
125 g/ha V0.5 g/kg of seed 12.5,%
A62 g/ha V 1 g/kg of seed 50,~
A52 g/ha V0,5 g/kg of seed 38,~
A62 g/ha V0.25 g/kg of seed 25
1;24~531
- 24 -
Herbicide Antidote - Relativeo. Applied amount No. Applied amount protective
acti on
B125 g/ha II 2 g/kg of seed 25%
B125 g/ha II 1 g/kg of seed 38%
B125 g/ha II0.5 g/kg of seed 38%
B125 g/ha IV 1 g/kg of seed 25%
B125 g/ha IV0.5 g/kg of seed 12,5%
B125 g/ha IV0.25 g/kg of seed 25,~
B125 g/ha V 1 g/kg of seed 25%
B 125 g/ha V 0.5 g/kg of seed 12,5%
B 125 g/ha V 0.25 g/kg of seed 25%
C 125 g/ha II 0.5 g/kg of seed 25~
C 125 g/ha II 0,5 g~kg of seed 38%
C 125 g/ha II 0.25 g/kg of seed 38%
C62 g/ha II 1 g/kg of seed 50
C62 g/ha II0.5 g/kg of seed 50,~
C62 g/ha II0.25 g/kg .of seed 50X
c31 g/ha II 1 g/kg of seed 50%
C31 g/ha II0.5 g/kg of seed 50%
C31 g/ha II0.25 g/kg of seed 50%
C125 g/ha III 0,5 g/kg of seed 25%
C125 g/ha III 0.25 g/kg of seed 25%
C62 g/ha III 1 g/kg of seed 25%
C62 g/ha III 0.5 g/kg of seed 50%
C62 g/ha III 0,25 g/kg of seed 50%
c31 g/ha III 0,5 g/kg of seed 38%
c31 g/ha III0,25 g/kg of seed 38,~
C125 g/ha IV . 1 g/kg of seed 25%
C125 g/ha IV 0,5 g/kg of seed 25
C125 g/ha IV0,25 g/kg of seed 25,~
C62 g/ha IV 1 g/kg of seed 50%
~ ;~40531
Herbicide Antidote ~elativë
No. Applied amount No. pplied amoUnt action
C62 g/ha IV0,~ g/kg of seed 50
C62 g/ha IV0.25 g/kg of seed 50%
C31 g/ha IV 1 g/k~ of seed 50
C31 g/ha IV0.5 g/kg of seed 50,~
C31 g/ha IV0,25 g/kg of seed 50,~
C125 g/ha V 1 g/kg of seed 25%
C125 g/ha V 0.5 ~/kg of seed 38,~
C125 g/ha V0,25 g/kg of seed 25,~
C62 g/ha V 1 g/kg of seed 50%
; C62 g/ha V 0.5 g/kg of seed 38%
62 ~/ha V0.25 g/kg of seed 12.5
C31 g/ha V 1 g/kg of seed 50,~
C31 g/ha V0,25 g/kg of seed 38%
E125 g/ha IIO.S g/kg of seed 12.5,~
E125 g/ha II0,25 g/kg of seed 25,~
E62 g/h~ ~I0.5 g/kg of seed 12,5,~
~E62 g/ha II0,25 g/kg of seed 12,5~
Example 2: Seed dressin~ with antidote: herbicide in the
post-emer~ence process on maize
Maize seeds of the "LG 5" variety are mixed in a glass
container with the substance to be tested as antidote. Seeds
and product are well mixed together by shaking and rotation.
Plastic pots ~upper diameter 11 cm) are filled with soil and
the dressed seeds are sown therein. After about 3 weeks,
when the plants have reached the three-leaf stage, the
herbicide is applied, and 14 days after the application of
the herbicide, the protective action of the antidote is
estimated in per cent. The plants treated with the herbicide
alone (no protective action) and the completely untreated
control plants (100% growth) provide reference values.
The results are summarised on the following pages.
~24V531
- 26 -
Herbicide Antidote Relative
l~o. Applied amount No. Applied amount action
A125 g/ha II 2 g/kg of seed 63%
A125 g/ha II 1 g/kg of seed 50%
A125 g/ha II0,5 g/kg of seed 12.5
A62 g/ha II 2 g/kg of seed 50~
A62 g/ha II 1 g/kg of seed 50%
A62 g/ha II0.5 g/kg of seed 38%
A125 g/ha III 1 g/kg of seed 12.5%
A125 g/ha III 0.5 g/kg of seed 38%
A125 g/ha III 0.25 g/kg o seed 12,5,~
A62 g/ha III 1 g/kg of seed 38,~
A62 g/ha III 0.5 g/kg of seed 63X
A62 g/ha III 0,25 g/kg of seed 12.5%
A125 g/ha IV 1 g/kg of-seed 50,~
A125 g/ha IV0.5 g/kg of seed 38,~
A125 g/ha IY0.25 g/kg of seed 25,~
A62 g/ha IV 1 g/kg of seed 50,~
A62 g/ha IV0.5 g/kg of seed 38X
A62 g/ha IV0.25 g/kg of seed 38%
A125 g/ha V 1 g/kg of seed 50~
A125 g/ha V 0.5 g/kg of seed 38%
A125 g/ha V0,25 g/kg of seed 38%
A62 g/ha V 1 g/kg of seed 50%
A62 g/ha V 0.5 g/kg of seed 38%
A62 g/ha V0,25 g/kg of seed 38%
B125 g/ha II2 g/kg o~ seed 63%
B125 g/ha II1 g/kg of seed 50%
B125 g/ha II0.5 g/kg of seed 38%
B62 g/h~ II2 g/kg of seed 50%
~L2~0531
Herbicide Antidote Relat ve
No Applied amount No. ~pplied amo t action
B62 g/ha II 1 g/kg of seed 38j~
B62 g/ha II 0.5 g/kg of seed 3~%
B125 g/ha III 1 g/kg of seed 25%
B125 g/ha III0.5 g/kg of seed 38%
B125 g/ha III0,25 g/kg of seed 38%
B62 g/ha III 1 g/kg of seed 25%
B62 ~/ha III0.5 g/kg of seed 38%
B62 g/ha III0,25 g/kg of seed 38%
B125 g/ha IV 1 g/kg of seed 50,~
B125 g/ha IV 0.5 g/kg of seed 38
B125 g/ha IV0,25 g/kg of seed 25%
B62 g/ha IV 1 g/kg of seed 38%
B62 g/ha IV ~5 g/kg of seed 38%
B62 g/ha IV0,25 g/kg of seed 38%
B125 g/ha V 1 g/kg of seed 50%
B125 g/ha V 0,5 g/kg of seed 38%
B125 g/ha V 0,25 g/kg of seed 38%
B62 g/ha V 1 g/kg of seed 50%
B62 g/ha V 0.5 g/kg of seed 38%
B62 g/ha V 0.25 g/kg of seed 38~
C125 g/ha II 1 g/kg of seed 25%
C125 g/ha II 0,5 g/kg of seed 50%
C125 g/ha II0.25 g/kg of seed 25%
C62 g/ha II 1 g/kg of seed 38%
C62 g/ha II 0.5 g/kg of seed 50%
C62 g/ha II0.25 g/kg of seed 38%
C125 g/ha III 1 g/kg of seed 12,5%
125 g/ha III0.5 g/kg of seed 25%
C62 g/ha III 1 g/kg of seed 12,5%
C 62 g/ha III0.5 g/kg of seed 12,5,~
~Z4~531
- 28 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount action
. _
C125 g/ha IV0,25 g/kg of seed l2,sX
C62 g/ha IV0,5 g/kg of seed 25%
C62 g/ha IV0,25 g/kg of-seed l2,5X
C31 g/ha IV 1 g/kg of seed 25%
C31 g/ha IY0.5 g/kg of seed 12.5,~
C125 g/ha V 1 g/kg of seed 63
C125 g/ha V 0,5 g/kg of seed 50j~
C125 g/ha V 0,25 g/kg of seed 50
C62 g/ha V 1 g/kg of seed 63,~
C62 g/ha V 0.5 g/kg of seed 50~
C62 g/ha V0.25 g/kg of seed 50%
C31 g/ha V 1 g/kg of seed 25%
C31 g/ha V 0.5 g/kg of seed 12.5%
C31 g/h~ V0.25 g/kg of seed 12.5%
D125 g,/ha II 1 g/kg of seed 25%
D125 g/ha II0-5 g/kg of seed 12.5X
D125 g/ha II0.25 g/kg of seed 25%
D62 g/ha II 1 g/kg of seed 38%
D62 g/ha II0.5 g/kg of seed 50%
D62 g/ha II0,25 g/kg of seed 50%
D31 g/ha II 1 g/kg of seed 25%
D31 g/ha II 0.5 g/kg of seed 38X
D31 g/ha II0,25 g/kg of seed 38X
D15 g/h8 II 1 g/kg of seed 25,~
D15 g/hs II0.5 g/k~ of seed 25%
D15 g/ha II0,25 g/kg of seed 25%
D 125 g/ha III 1 y/kg of seed 12,5%
~Z~0531
- 29 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount action
~ . . _
D 125 g/ha III 0,25 g/kg of seed 12.5,~
D 62 g/ha III ~ ~/kg of seed 25%
D 62 g/ha III 0.5 g/kg of seed 25,~
D 62 g/ha III 0.25 g/kg of seed 25%
D31 g/ha III 1 g/kg of seed 12,5%
D31 g/ha III 0,5 g/kg of seed 12.5,~
31 g/ha III 0.25 g/kg Of seed 12-5%
D125 g/ha IV 1g/kg of seed 63%
D125 g/ha IV0,5g/kg of seed 50%
1)125 g/ha IV0.25g/kg of seed 38%
D62 g/ha IV 1g/kg of seed 63
D62 g/ha IV0.5g/kg of seed 50,~
D62 g/ha IV0,25g/kg of seed 63
D31 g/ha IV 1g/kg of seed 50~
D31 g/ha IV0-5 g/kg of seed 38%
D31 g/ha IV0,25 g/kg of seed 38
D15 g/ha IV1 g/kg of seed 25,~
D15 g/ha IV0.5 g/kg of seed 25%
D15 g/ha IV0.25g/kg of seed 12-5
D125 g/ha V 1g/kg of seed 25%
D125 g/ha V 0.5g/kg of seed 12.5%
D62 g/ha V 1g/kg of seed 38%
D62 g/ha V 0.5g/kg of seed 25%
D62 g/ha Vo.25 g/kg of seed 25%
D31 g/ha V1 g/kg of seed 12.5%
D31 g/ha V0.5 g/kg of seed 12.5%
D 31 g/ha V0.25 g/kg of seed 12.5%
1240531
- 30 -
Example 3: Tank mixture in the pre-emer~ence_process
on maize
Maize seeds of the l'LG 5" variety are sown in plastic
pots (upper diameter 11 cm3 each containing 0.5 litre of
soil in a greenhouse. After the seeds have been covered,
the substance to be tested as safener (antidote) and the
herbicide are applied together as a tank mixture to the
surface of the soil. The protective action of tlle antidote
is estimated in per cent 21 days after application. The
plants treated with the herbicide alone (no protective
action) and the completely untreated control plants
(100% growth~ provide reference values. The results are
summarised below.
Relative
Herbicide Antidote protective
No. Applied amount No. Applied amount action
C31 g/ha II31 g/ha . 12,5
; C15 g/ha II15 g/ha 25~
C7 g/ha II7 g/ha 38%
C15 g/ha III15 g/ha 25
C7 g/ha III7 g/ha 25~
C31 g/ha V31 g/ha 12.57;
C15 g/ha VlS g/ha 25
C7 g/ha V7 g/ha 38~
E125 g/ha II125 g/ha 25%
E62 g/ha II62 g/ha 12.5
E125 g/ha III125 g/ha 25%
E62 g/ha III62 g!ha 12.5
E31 g/ha III31 g/ha 25%
E15 g/ha III15 g/ha 25%
lZ~0531
- 31 -
Example 4: Seed dressing with antidote: herbicide in the
pre-emer~ence process on sor~hum
Sorhum seeds are mixed in a glass container with
the substance to be tested as antidote. Seeds and product
are well mixed together by shaking and rotation. Plastic
pots (upper diameter 11 cm) are filled with soil, and the
dressed seeds are sown therein. After the seeds have been
covered, the herbicide is applied in the pre-emergence
process. The protective action of the antidote is
estimated in per cent 14 days after the application of the
herbicide. The plants treated with the herbicide alone
(no protective action) and the completely untreated control
plants (1~0% growth) provide reference values. The results
are summarised below.
.
Herbicide Antidote Relative
No. Applied amount No. Applied amount proitective
A125 g/ha II 1 g/kg of seed 12.5%
A125 g/ha II0.5 g/kg of seed 12,5,~
A62 g/ha II 1 g/kg of seed 25%
A62 g/ha II0.5 g/kg of seed 12,5%
A62 g/ha II0,25 g/kg of seed 12.5%
A31 g/ha II 1 g/kg of seed 38%
A31 g/ha II0.5 g/kg of seed 50%
A31 g/ha II0.25 g/kg of seed 38%
A15 g/ha II 1 g/kg of seed 50%
A15 g/ha II0.5 g/kg of seed 63%
A15 g/ha II0.25 g/kg of seed 63%
A15 ~/ha IV 1 g/kg of seed 25%
A15 g/ha IV0.5 g~kg of seed 25%
A15 g/ha IV ~25 g/kg of seed 25,%
lZ40
- 32 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount protective
A15 g/ha V 0.5 g/kg of seed 12,5%
B125 g/ha II 1 g/kg of seed 50
B125 g/ha II 0.5 g/kg of seed 50,~
B125 g/ha II0,25 g/kg of seed 50
B63 g/ha II 1 g/kg of seed 63
B63 g/ha II 0.5 g/kg of seed 63,~
B63 g/ha II 0.25 g/lcg of seed 50~
B31 g/ha II 1 g/kg of seed 38%
B31 g/ha II 0.5 g/kg of seed 50%
B31 g~ha II0.25 g/kg- of seed 38j~
B125 g/ha - IV 1 g/kg of seed 25
B125 g/h~ IV 0.5 g/kg of seed 38j~
B125 g/ha IV0.25 g/kg of seed 38
B62 g/ha IY 1 g/kg of seed 12.5,~
B62 g/ha IV 0-5 g/kg of seed 38X
B62 g/ha IV0.25 g/kg of seed 50~
B31 g/ha IV 1 g/kg of seed 25%
B31 g/ha IV 0.5 g/kg of seed 25,~
B31 g/ha IV0.25 g/kg of seed 25~2~
B125 g/ha V 1 g/kg of seed 50%
B125 g/ha V 0.5 g/kg of seed 38,%'
B125 g/ha V 0.25 g/kg of seed 38%
B62 g/ha V 1 g/kg of seed 38~
B62 g/ha V 0.5 g/kg of seed 38%
B62 g/ha V 0.25 g/kg of seed 25,~
B31 g/ha V 1 g/kg of seed 25j~
B31 g/ha V 0.5 g/kg of seed 25%
B31 g/ha V 0.25 g/kg of seed 12.5
.
~24~S3~
- 33 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount protective
C125 g/ha II 1 g/k~ of seed 12.5%
C125 g/ha II0.5 g/kg of seed 12.5
C125 g/ha II0.25 g/kg of seed 12,5
C62 g/ha II 1 g/kg of seed 25%
C62 g/ha II0.5 g/kg of seed 25%
C31 g/ha II 1 g/kg of seed 38,~
C31 g/ha II~5 g/kg of seed 38,~ -
C31 g/ha II0.25 g/kg of seed 38%
C15 g/ha Il1 g/kg of seed 50
C15 g/ha II0-5 g/kg of seed 50%
C15 g/ha II0.25 g/kg of seed 50,~
C31 ~/ha IV 1 g/kg of seed 12.5%
C31 g/ha IV0.5 g/kg of seed 25
C31 g/ha IV0.25 g/kg of seed 25,%
C15 g/ha IY 1 g/kg of seed 38,~
C15 g/ha IV0-5 g/kg of seed 50
C15 g/ha IV0.25 g/kg of seed 38~
C31 g/ha V 1 g/kg of seed 25%
C31 g/ha V 0.5 g/kg of--seed 12,52.
C15 g/ha V 1 g/kg of seed 25~
C15 g/ha V 0,5 g/kg of seed 25%
C15 g/ha V0.25 g/kg of seed 12.S%
D31 g/ha IV 1 g/kg of seed 25%
D31 g/ha IV0.5 g/kg of seed 25%
D31 g/ha IV0.25 g/kg of seed 12.5%
D15 g/ha IV1 g/kg of seed 38,~
I)15 g/ha IV0.5 g/kg of seed 38,%
D 15 g/ha IV0.25 g/kg of seed 25%
~Z~(~531
- 34 -
Herbicide Antidote Relative
No Applied amount No Applied amount protective
E 31 g/ha V 1 ~/kg of seed 25,%
E 31 g/ha V 0,S g/kg of seed 2s%
E 31 g/ha V0 25 ~/kg of seed 12 5%
E 15 g/ha V 1 g/kg of seed 12,5%
E 15 g/ha V 0,5 g/kg oi: seed 12,5
15 ~/'na V 0.25 g/kg of seed 12.5~
Example 5: Seed dressin~ with antidote: herbicide in the
post-emergence process on sor~hum
Sorghum seeds of the G 623 variety are mixed in a glass
container with the substance to be tested as antidote.
Seeds and product are well mixed together by shaking and
rotation. Plastic pots (upper diameter 11 cm) are filled
with soil, and the dressed seeds are sown therein. After
the seeds have been covered, the herbicide is applied in the
post-emergence process. The protective action of the
an~idote is estimated in per cent 18 days after application
of the herbicide. The plants treated with the herbicide
alone (no protective action) and the completely untreated
control plants (100% growth) provide reference values.
The results are summarised below.
Herbicide Antidot~e protective
No. Applied amount No. Applied amUnt action
B 12S g/ha II 1 g/kg ~of: seed 25%
B 125 g/ha II 0.5 g/kg of seed 25%
B 125 g/ha II 0,25 g/kg of seed 12,5%
B 62 g/ha II 1 g/kg o:f seed 25%
, .
~Z40~3~
- 35 -
Relative
Herbicide Antidote protective
No. Applied amount No. Applied amount action .
B62 g/ha II0.5 g/kg~ o~ seed 25%
B62 g/ha II0,25 g/kg of seed 12.5%
B31 g/ha II 1 g/kg of seed 25%
B31 g/ha II0!5 g/kg of seed 252~
B31 g/ha II0.25 g/kg of seed 12.5%
B125 g/ha IV 1 g/kg of seed 25%
B125 g/ha IV0.5 g/kg of seed 25%
B125 g/ha I~r 0,25 g/kg of seed 25%
B62 g/ha IV 1 g/kg of seed 25,~
B62 g/kg IV0.5 g/kg of seed 25%
B62 g/ha IV0.25 g/kg of seed 25%
B31 g/ha IV1 g/kg of seed 25%
B31 g/ha IV0,5 g/kg of seed 25%
B31 g/ha IV0,25 g/kg of seed 25,~
B31 g/ha V 1 g/kg of seed 12.5%
B31 g/ha V0. 5 g/k8 of seed 12,5,~
B15 g/ha V 1 g/kg of seed 25%
B15 g/ha V 0.5 g/kg of seed 25%
B15 g/ha V0.25 g/kg of seed 25%
C125 g/ha II 1 g/kg of seed 25%
C125 g/ha II0.5 g/kg of seed 12,5
C62 g/ha II 1 g/kg of seed 25%
C62 g/ha II0.5 g/kg of seed 12,5j~
C62 g/ha II0,25 g/kg of seed 12.5%
C31 g/kg II 1 g/kg of seed 38%
C31 g/ha II0.~ g/kg of seed 38,~
C31 g/ha II0.25 g/kg of seed 25,~
C15 g/ha II1 g/kg of seed 38%
15 g/ha II0,5 g/kg of seed 38
1240S31
- 36 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount PctiOn
C 15 g/ha II0,25 g/kg of seed 25%
C 31 I~/ha IV 1 g/kg of seed 12,5%
C 31 g/ha IV0.5 g/kg of seed 25%
C 31 g/ha IV0,25 g/kg of seed 25%
C 15 g/ha IV 1 g/kg of seed 25%
C 15 g/ha IV0.5 g/kg of seed 25,7;
C 15 g/ha IV0,25 g/kg of seed 25%
C 62 g/ha V 1 g/kg of seed 12,5%
C 62 g/ha V 0.5 g/kg of seed 12,5,~
C 62 g/ha V0.25 g/kg of seed 12.5,~
C 31 g/ha V 1 g/kg of seed 25X
C 31 g/ha V 0,5 g/kg of seed 25
C 31 g/ha V0.25 g/kg of seed 12,5,~
C 15 g/ha V 1 g/kg of seed 25%
C 15 g/ha V0.5 g/kg of seed 25~
C 15 g/ha V0.25 g/ko of seed 25%
D 62 g/ha IV1 g/kg of seed 38%
D 62 g/ha IV0.5 g/kg of seed 38%
D 62 g/ha IV0.25 g/kg of seed 38%
D 31 g/ha IV1 g/kg of seed 38,~
D 31 g/ha IV0,5 g/kg of seed 38%
D 31 g/ha IV0.25 g/kg of seed 38%
D 15 g/ha IV1 g/kg of seed 25%
D 15 g/ha IV0.5 g/kg oi: seed 25%
D 15 g/ha IV0.25 g/kg of seed 25~2~
~240531
Example 6: Tank mixture in the pre-emer~ence process
on sor~hum
Plastic containers (25 cm long x 17 cm wide x 12 cm high)
are filled with sandy loam soil, and sorghum seeds of the
Funk FG 522 variety are sown therein. After the seeds have
been covered, the substance to be tested as antidote (safener)
and the herbicide are applied together as a tank mixture
to the surface of the soil. The protective action of the
antidote is estimated in per cent 30 days after application.
The plants treated with the herbicide alone (no protective
action) and the completely untreated control plants
(100% growth) provide reference values. The results are
summarised below.
. Relative
Herbicide Antldote protective
No. Applied amount No. Applied amount action
-
E 125 g/ha IV 125 g/ha 38%
E 62 g/ha lV 62 g//ha 25,~
Example 7: Tank mixture in the pre-emer~ence process
on barleY
Barley seeds are sown, in a greenhouse, in plastic pots
(upper diameter 11 cm) each containing 0.5 litre of soil.
After the seeds have been covered, the substance to be tested
as antidote and the herbicide are applied together as a tank
mixture to the surface of the soil. The protective action
of the antidote is estimated in per cent 21 days after
application. The plants treated with the herbicide alone
(no protective action~ and the completely untreated control
plants ~100% growth) provide reference values. The results
are summarised below.
~Z4053~
Herbicide Antidote Relative
No. Applied amount NoO Applied amount acrtiOntive
.
A125 g/ha II125 g/ha 63~
A 62 g/ha II62 g/ha 25%
A125 ~/ha III125 g/ha 50~
A 62 g/ha III62 g/ha 25X
A 31 g/ha III31 g/ha 12.5
A125 g/ha V125 g/ha 63
. A62 ~/ha V 62 g/ha 38~
A 31 g/ha V 31 g/ha 12.5%
C125 g/ha II125 8/ha 25X
`I C62 g/ha II62 g/ha 25%
C125 g/hal III125 g/ha 25%
C 62 g/ha III62 g/ha 25
E125 g/hal II125 g/ha 12.5
E 62 g/ha II62 g/ha 25X
,E.31 g/ha II31 g/ha 12.5~
Example 8: Tank mixture in the pre-emergence process
on soYa-bean
Plasticcontainers (upper diameter 6 cm) are filled with
sandy loam soil, and soybean seeds of the "Hark" variety are
sown therein. After the seeds have been covered, the
substance to be tested as antidote and the herbicide in
diluted solution are applied as a tank mixture to the surface
of the soil. The protective action of the antidote is
estimated in per cent 21 days after application of the
herbicide. The plants treated with the herbicide alone (no
protective action) and the completely untreated control
plants (100~/o growth) provide reference values. The results
are summarised below.
~Z40531
- 39 -
Herbicide Antidote Relative
No. Applied amount No. Applied amount prctiOntive
D 125 g/ha IV 125 g/ha 25%
I D 62 g/ha IV 62 g/ha 12.5%
D 31 g/ha IV 31 g/h~ 50%
