MELANGES DEFOLIANTS ET (OU) REGULATEURS DE LA CROISSANCE DES PLANTES, ET LEUR UTILISATION

PREPARATIONS FOR DEFOLIATING AND/OR REGULATING THE GROWTH OF PLANTS AND THEIR USE

Abrégé anglais

ABSTRACT
Preparations for defoliating and/or regulating
the growth of plants and their use
A synergistic mixture of (i) a defoliating and/or
growth-regulating compound selected from 1,2,3-thiadiazol-
5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide deriva-
tives with (ii) a basically reactive substance is used for
defoliating and/or regulating the growth of plants, prefer-
ably cotton plants. Preparations suitable for such use
comprise the aforesaid constituents, the ratio by weight of
the defoliating and/or growth-regulating compound to the
basically reactive substance preferably being 1:0.5 to
1:1000.
The defoliating and/or growth-regulating compound is,
for example, 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and the
basically reactive substance is, for example, an alkali
hydroxide, amine, carbonate, phosphate or alkali salt of a
monocarboxylic acid.

Revendications

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A preparation for defoliating ox regulating the growth
of plants, which comprises a defoliating or growth-regulating
compound selected from 1,2,3-thiadiazol-5-yl-urea deriva-
tives and 1,2,3-thiadiazolin-2-ide derivatives, in admix-
ture or conjunction with an alkaline reacting substance,
the ratio by weight of the defoliating or growth-regulating
compound to the alkaline reacting substance being within the range
of from 1:0.5 to 1:1000.
2. A preparation as claimed in claim 1, wherein the de-
foliating or growth-regulating compound is a 1,2,3-thiadia-
zol-5-yl-urea derivative of the general formula I
<IMG> (I)
in which R1 represents a hydrogen atom or a C1-C5-alkyl group,
R2 represent a C1-C5-alkyl group, a C5-C8-cycloalkyl group,
a phenyl, halogenated phenyl, C1-C4-alkylphenyl, C1-C4-
alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an
unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyr-
imidyl group substituted by one or more substituents selected
from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms,
nitro groups and trifluoromethyl groups, or R1 and R2 together
with the adjacent nitrogen atom represents a morpholino,
piperidino or pyrrolidino group, R3 represents a hydrogen
atom or a C1-C5-alkyl group, and X represents an oxygen or
sulphur atom.
3. A preparation as claimed in claim 2, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is selected from the group
consisting of 1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-Phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea

1-Cyclohexyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3,4-Dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-Methyl-3-(1,2,3-thiadiazol-5-yl)-urea
1,1-Dimethyl-3-(1,2,3-thiadiazol-5-yl)-urea
1,1-Dimethyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-Methyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea
1-(4-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-thiourea
1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and
1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
4. A preparation as claimed in claim 2, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-phenyl-3-(1,2,3-thia-
diazol-5-yl)-urea.
5. A preparation as claimed in claim 2, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-phenyl-1-methyl-3-
(1,2,3-thiadiazol-5-yl)-urea.
6. A preparation as claimed in claim 2, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-
thiadiazol-5-yl)-urea.
7. A preparation as claimed in claim 1, wherein the de-
foliating or growth-regulating compound is a 1,2,3-thiadia-
zolin-2-ide derivative of the general formula II
26

<IMG>
(II)
in which R1 represents a hydrogen atom or a C1-C5-alkyl group,
R2 represents a hydrogen atom, a C1-C5-alkyl group, a C5-C8-
cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-alkyl-
phenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethyl-
phenyl group, an unsubstituted pyridyl or pyrimidyl group or
a pyridiyl or pyrimidyl group substituted by one or more sub-
stituents selected from C1-C4-alkyl groups, C1-C4-alkoxy
groups, halogen atoms, nitro groups and trifluoromethyl
groups, or R1 and R2 together with the adjacent nitrogen
atom represent a morpholino, piperidino or pyrrolidino
group, B represents an alkali metal atom or a monovalent
equivalent of zinc, manganese, calcium, magnesium or barium,
and X represents an oxygen or sulphur atom.
8. A preparation as claimed in claim 7, wherein B repre-
sents a lithium, sodium or potassium atom.
9. A preparation as claimed in claim 7, wherein the 1,2,3-
thiadiazolin-2-ide derivative is selected from the group
consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium
salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium
salt x8H2O
5-(Phenylcarbamoyliminol)-1,2,3-thiadiazolin-2-ide, potassium
salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium
salt x4H2O
5-(Methylphenylcarbamoyliminol-1,2,3-thiadiazolin-2-ide,
sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH2O
27

5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
lithium salk xH2O
5-(2 Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH20
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium
salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt
x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese
salt x3H20
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium
salt x3H20.
10. A preparation as claimed in claim 7, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the calcium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
11. A preparation as claimed in claim 7, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the magnesium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
12. A preparation as claimed in claim 7, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the manganese salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
13. A preparation as claimed in claim 13, wherein the
alkaline reacting substance is an alkali hydroxide, an amine,
a carbonate, a phosphate or an alkali salt of a monocarboxylic
acid.
14. A preparation as claimed in claim 13, wherein the alkali
hydroxide is sodium or potassium hydroxide.
15. A preparation as claimed in claim 13, wherein the amine
28

is triethylamine, diethanolamine, triethanolamine, triiso-
propanolamine or hexamethylenetetramine.
16. A preparation as claimed in claim 13, wherein the car-
bonate is sodium carbonate, potassium carbonate or ammonium
carbonate.
17. A preparation as claimed in claim 13, wherein the phos-
phate is trisodium phosphate, tripotassium phosphate, tetra-
sodium pyrophosphate or tetrapotassium pyrophosphate.
18. A preparation as claimed in claim 13, wherein the alkali
salt of a monocarboxylic acid is sodium oleate.
19. A preparation as claimed in claim 1, which comprises
1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea as the defoliating
or growth-regulating compound in admixture with potassium
hydroxide, potassium carbonate, ammonium carbonate, tetra-
potassium pyrophosphate, triethylamine, triethanolamine or
sodium oleate. as the alkaline reacting substance.
20. A preparation as claimed in claim 1, which comprises
1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea as the defol-
iating or growth-regulating compound in admixture with pot
assium carbonate as the alkaline reacting substance.
21. A preparation as claimed in claim 1, which comprises
the calcium salt of 5-(phenylcarbamoylimino)-1,2,3-thiadia-
zolin-2-ide as the defoliating or growth-regulating compound
in admixture with potassium carbonate as the alkaline reacting
substance
22. A preaparation as claimed in claim 1 having a pH-value
greater than 8.
23. A preparation as claimed in claim 22, having a pH-value
within the range of from 9.5 to 11.5.
24. A preparation as claimed in claim 1, which also contains
at least one of a liquid carrier and a solid carrier.
29

25. A preparation as claimed in claim 24, containing 5 to
95% by weight of the defoliating or growth-regulating
compound and the alkaline reacting substance and 95 to 5%
by weight of at least one of the liquid and solid carriers.
26. A preparation as claimed in claim 1, which also contains
a surface-active agent.
27. A preparation as claimed in claim 26, containing the
surface-active agent in an amount of up to 30% by weight.
28. A preparation as claimed in claim 1, 2 or 3, which also
contains one or more active substances selected from defol-
iating agents, plant-protecting agents and pesticides other
than 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-
thiadiazolin-2-ide derivatives.
29. A preparation as claimed in claim 1,2 or 3, which is in
the form of a powder, a strewable preparation, a solution,
an emulsion or a suspension.
30. A preparation selected from the group comprising of:
a) 95% by weight of mixture
4% by weight of kaolin
1% by weight of surface-active agents based on the
sodium salt of N-methyl-N-oleyl-taurine
and the calcium salt of lignin sulphon-
ic acid
b) 80% by weight of mixture
10% by weight of calcium salt of lignin sulphonic acid
3% by weight of ammonium salt of the monosulphuric
acid ester of tetraethylene glycol
nonyl phenyl ether
7% by weight of colloidal silicic acid
c) 20% by weight of mixture
70% by weight of tonsil
8% by weight of cellulose pitch
2% by weight of wetting agent based on a fatty acid
condensation product

and
d) 5% by weight of mixture
80% by weight of tonsil
10% by weight of cellulose pitch
5% by weight of wetting agent based on a fatty acid
condensation product,
31

said mixture being the mixture of a defoliating or growth-
regulating compound selected from 1,2,3-thiadiazol-5-vl-urea
derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with an alkaline
reacting substance, the ratio by weight of the defoliating or growth-
regulating compound to the alkaline reacting substance being within
the range of from 1:0.5 to 1:1000.
31. A method of defoliating or regulating the
growth of a living plant at the stage of having at least 5
foliage leaves, wherein the living plant is treated with a
mixture comprising (i) a defoliating or growth regulating
compound selected from 1,2,3-thiadiazol-5-yl-urea derivatives
and 1,2,3-thiadiazolin-2-ide derivatives and (ii) an alkaline
reacting substance, the ratio by weight of the defoliating or
growth-regulating compound to the alkaline reacting substance
by within the range of from 1:0.5 to 1:1000.
32. A method as claimed in claim 31, wherein the
defoliating or growth-regulating compound is a 1,2,3-thiadia-
zol-5-yl-urea derivative of the general formula I given in
claim 2, in which R1, R2, R3 and X have the meanings given
in claim 2.
33. A method as claimed in claim 32, wherein the
1,2,3-thiadiazol-5-yl-urea derivative is selected from the
group consisting of: 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-
urea; 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea;
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclo-
hexyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-
(1,2,3-thiadiazol-5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-
thiadiazol-5-yl)-urea; 1-(3-methylphenyl)-3-(1,2,3-thiadiazol-
5-yl)-urea; 1-(3,4-dichlorophenyl)-3-(1,2,3-thiadiazol-5-
yl)-urea; 1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1,1-
dimethyl-3-(1, 2, 3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-methyl-
(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-methyl-3-(1,2,3-thia-
32

diazol-5-yl)-urea; 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
1-(4-chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-thiourea;

1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and
1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
34. A method as claimed in claim 32, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-phenyl-3-(1,2,3-thia-
diazol-5-yl)-urea.
35. A method as claimed in claim 32, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-phenyl-1-methyl-3-
(1,2,3-thiadiazol-5-yl)-urea.
36. A method as claimed in claim 32, wherein the 1,2,3-
thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-
thiadiazol-5-yl)-urea.
37. A method as claimed in claim 32, wherein the defoliating
or growth-regulating compound is a 1,2,3-thiadiazolin-2-ide
derivative of the general formula II given in claim 7, in
which R1, R2, B and X have the meanings given in claim 7.
38. A method as claimed in clalm 37, wherein B represents
a lithium, sodium or potassium atom.
39. A method as claimed in claim 37, wherein the 1,2,3-
thiadiazolin-2-ide derivative is selected for the group
consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium
salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium
salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium
salt xH2O
34

5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium
salt x4H2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt xH20
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH2O
5-(Methylphenylcarbamoylmino)-1,2,3-thiadiazolin-2-ide,
lithium salt xH2O
5-(2-Pyridylcarbamoylimino )-1,2,3-thiadiazolin-2-ide,
sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium
salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc salt
x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese
salt x3H2O and
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium
salt x3H2O.
40. A method as claimed in claim 37, wherein the 1,2,3-
thiadiazolin-2-ide, derivative is the calcium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
41. A method as claimed in claim 37, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the magnesium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
42. A method as claimed in cl.aim 37, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the manganese salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
43. A method as claimed in claim 31, wherein the alkaline
reacting substance is an alkali hydroxide, an amine, a

carbonate, a phosphate or an alkali salt of a monocarboxylic
acid.
44. A method as claimed in claim 43, wherein the alkali
hydroxide is sodium or potassium hydroxide
45. A method as claimed in cliam 43, wherein the amine
is triethylamine, diethanolamine, triethanolamine, triiso-
propanolamine or hexamethylenetetramine.
46. A method as claimed in claim 43, wherein the carbonate
is sodium carbonate, potassium carbonate or ammonium carbon-
ate.
47. A method as claimed in claim 43, wherein the phosphate
is trisodium phosphate, tripotassium phosphate, tetrasodium
pyrophosphate or tetrapotassium pyrophosphate.
48. A method as claimed in claim 43, wherein the alkali
salt of a monocarboxylic acid is sodium oleate.
49. A method as claimed in claim 31, wherein the mixture
is a mixture comprising 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-
urea and potassium hydroxide, potassium carbonate, ammonium
carbonate, tetrapotassium pyrophosphate, triethylamine,
triethanolamine or sodium oleate.
50. A method as claimed in claim 31, wherein the mixture is
a mixture comprising 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-
yl)-urea and potassium carbonate.
51. A method as claimed in claim 31, wherein the mixture
is a mixture comprising the calcium salt of 5-(phenylcarba-
moylimino)-1,2,3-thiadiazolin-2-ide and potassium carbonate.
52. A method as claimed in claim 31, wherein the pH-value
of the mixture is greater then 8.
53. A method as claimed in claim 52, wherein the pH-value
of the mixture is within the range of from 9.5 to 11.5.
54. A method as claimed in claim 31, wherein the mixture
also contains at least one of a liquid carrier and a solid
carrier.
36

55. A method as claimed in claim 54, wherein the mixture
contains 5 to 95% by weight of the defoliating or growth-
regulating compound and the alkaline reacting substance
and 95 to 5% being of at least one of the liquid and solid
carriers.
56. A method as claimed in claim 31, wherein the mixture
also contains a surface-active agent.
57. A method as claimed in claim 56, wherein the mixture
contains up to 30% by weight of the surface-active agent.
58. A method as claimed in claim 31, 32, or 33, wherein the
mixture also contains one or more active substances selected
from defoliating agents, plant-protecting agents and pestici-
des other than 1,2,3-thiadiazol-5-yl-urea derivatives and
1,2,3-thiadiazolin-2-ide derivatives.
59. A method as claimed in claim 31, 32 or 33, wherein the
mixture is in the form of a powder, a strewable preparation,
a solution, an emulsion or a suspension.
60. A method as claimed in claim 31, wherein the mixture
is selected from the group consisting of:
a) 95% by weight of mixture
4% by weight of kaolin
1% by weight of surface-active agents based on the
sodium salt of N-methyl-N-oleyl-taurine
and the calcium salt of lignin sulphon-
ic acid
b) 80% by weight ofmixture
10% by weight of calcium salt of lignin sulphonic acid
3% by weight of ammonium salt of the monosulphuric
acid ester of tetraethylene glycol
nonyl phenyl ether
7% by weight of colloidal silicic acid
c) 20% by weight of mixture
70% by weight of tonsil
8% by weight of cellulose pitch
2% by weight of wetting agent based on a fatty acid
37

condensaton product
and
d) 5% by weight of mixture
80% by weight of tonsil
10% by weight of cellulose pitch
5% by weight of wetting agent based on a fatty acid
condensation product
38

said mixture being the mixture of a defoliating or growth-
regulating compound selected from 1,2,3-thiadiazol-5-yl-urea
derivatives and 1,2,3-thiadiazolin-2-ide derivatives, with
an alkaline reacting substance, the ratio by weight of the
defoliating or growth-regulating compound to the alkaline
reacting substance being within the range of from 1:0.5 to
1:1000.
61. A method of defoliating or regulating the growth
of plants, at the stage of having at least 5 foliage leaves
in a crop area, wherein the crop area is treated with a mixture
comprising (i) a defoliating or growth-regulating compound
selected from 1,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3-
thiadiazolin-2-ide derivatives and (ii) an alkaline reacting
substance, the ratio by weight of the defoliating growth-
regulating compound to the alkaline reacting substance being
within the range of from 1:0.5 to 1:1000.
62. A method as claimed in claim 61, wherein the
defoliating or growth-regulating compound is a 1,2,3-thia-
diazol-5-yl-urea derivative of the general formula I given
in claim 2, in which R1, R2, R3 and X have the meanings given
in claim 2.
63. A method as claimed in claim 62, wherein the
1,2,3-thiadiazol-5-yl-urea derivative is selected from the
group consisting of: 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea;
1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(4-chloro-
phenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-cyclohexyl-3-(1,2,3-
thiadiazol-5-yl)-urea; 1-(3-chlorophenyl)-3-(1,2,3-thiadiazol-
5-yl)-urea; 1-(4-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea;
1-(3-methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-(3,4-
dichlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea; 1-methyl-3-
(1,2,3-thiadiazol-5-yl)-urea; 1,1-dimethyl-3-(1,2,3-thiadiazol-
5-yl)-urea; 1,1-dimethyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-
urea; 1-methyl-3-methyl-3-(1,2,3-thiadiazol-5-yl)-urea; 1-
phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea;
39

1-(4-Chlorophenyl)-3-(1,2,3 thiadiazil-5-yl)-thiourea
1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Methyl-2-pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(2-Pyrimidyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea and
1-(6-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
64. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-
5-yl-urea derivative is 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea.
65. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-
5-yl-urea derivative is 1-phenyl-1-methyl-3-(1,2,3-thiadiazol-5-yl)-
urea.
66. A method as claimed in claim 62, wherein the 1,2,3-thiadiazol-5-
yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea.
67. A method as claimed in claim 61, wherein the defoliating or grow-
th-regulating ccmpound is a 1,2,3-thiadiazolin-2-ide derivative of the
general formula II given in claim 7, in which R1, R2, B and X have the
meanings given in claim 7.
68. A method as claimed in claim 67, wherein B represents a lithium,
sodium or potassium atom.
69. A method as claimed in claim 67, wherein the 1,2,3-thiadiazolin-
2-ide derivative selected from the group consisting of:
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt x4H2O

5-(Methylphenylcarbamoylimino)-1,2,3-thiadaizolin-2-ide,
sodium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH2O
5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
lithium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt x1.5 H2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
potassium salt xH2O
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
lithium salt xH2O
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt xH2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium
salt x2H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, zinc
salt x3H2O
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, manganese
salt x3H2O and
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium
salt x3H2O.
70. A method as claimed in claim 67, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the calcium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
71. A method as claimed in claim 67, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the magnesium salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
72. A method as claimed in claim 67, wherein the 1,2,3-
thiadiazolin-2-ide derivative is the manganese salt of 5-
(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
73. A method as claimed in claim 61, wherein the alkaline
reacting substance is an alkali hydroxide, an amine, a car
bonate, a phosphate or an alkali salt of a monocarboxylic
acid.
41

74. A method as claimed in claim 73, wherein the alkali
hydroxide is sodium or potassium hydroxide.
75. A method as claimed in claim 73, wherein the amine
is triethylamine, diethanolamine, triethanolamine, triiso-
propanolamine or hexamethylenetetramine.
76. A method as claimed in claim 73, wherein the carbonate
is sodium carbonate, potassium carbonate or ammonium car-
bonate.
77. A method as claimed in claim 73, wherein the phosphate
is trisodium phosphate, tripotassium phosphate, tetrasodium
pyrophosphate or tetrapotassium pyrophosphate.
78. A method as claimed in claim 73, wherein the alkali
salt of a monocarboxylic acid is sodium oleate.
79. A method as claimed in claim 61, wherein the mixture is
a mixture comprising 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-
urea and potassium hydroxide, potassium carbonate, ammonium
carbonate, tetrapotassium pyrophosphate, triethylamine, tri-
ethanolamine or sodium oleate.
80. A method as claimed in claim 61, wherein the mixture is
a mixture comprising 1-(2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-
urea and potassium carbonate.
81. A method as claimed in claim 61, wherein the mixture
is a mixture comprising the calcium salt of 5-(phenylcarba-
moylimino)-1,2,3-thiadiazolin-2-ide and potassium carbonate.
82. A method as claimed in claim 61, wherein the pH-value of
the mixture is greater than 8.
83. A method as claimed in claim 82, wherein the pH-value
of the mixture is within the range of from 9.5 to 11.5.
84. A method as claimed in claim 61, wherein the mixture
also contains at least one of a liquid carrier and a solid
carrier.
85. A method as claimed in claim 84, wherein the mixture
contains 5 to 95% by weight of the defoliating or growth-
42

regulating compound and the alkaline reacting substance and
95 to 5% by weight of at least one of the liquid and solid
carriers.
86. A method as claimed in claim 61, wherein the mixture
also contains a surface-active agent.
87. A method as claimed in claim 86, wherein the mixture
contains up to 30% by weight of the surface-active agent.
88. A method as claimed in claim 61, 62, or 63, wherein the
mixture also contains one or more active substances selected
from defoliating agents, plant-protecting agents and pestici-
des other than 1,2,3-thiadiazol-5-yl-urea derivatives and
1,2,3-thiadiazolin-2-ide derivatives.
89. A method as claimed in claim 61, 62, or 63, wherein the
mixture is in the form of a powder, a strewable preparation,
a solution, an emulsion or a suspension.
90. A method as claimed in claim 61, wherein the mixture is
selected from the group consisting of:
a) 95% by weight of mixture
4% by weight of kaolin
1% by weight of surface-active agents based on the
sodium salt of N-methyl-N-oleyl-taurine
and the calcium salt of lignin sulphon-
ic acid
b) 80% by weight of mixture
10% by weight of calcium salt of lignin sulphonic acid
3% by weight of ammonium salt of the monosulphuric
acid ester of tetraethylene glycol
nonyl phenyl ether
7% by weight of colloidal silicic acid
c) 20% by weight of mixture
70% by weight of tonsil
8% by weight of cellulose pitch
2% by weight of wetting agent based on a fatty acid
condensation product
43

and
d) 5% by weight of mixture
80% by weight of tonsil
10% by weight of cellulose pitch
5% by weight of wetting agent based on a fatty acid
condensation product
said mixture being the mixture of a defoliating or growth-
regulating compound selected from 1,2,3-thiadiazol-5-yl-
urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives,
with an alkaline reacting substance, the ratio by weight of
the defoliating or growth-regulating compound to the alkaline
reacting substance being within the range of from 1:0.5 to
1:1000.
91. A method as claimed in claim 61, wherein the
total amount of the defoliating or growth-regulating compound
and the alkaline reacting substance used for the treatment
is within the range of from 1 to 10,000 grams per hectare.
92. A method as claimed in claim 91, wherein the
total amount is within the range of from 10 to 1000 grams per
hectare.
93. A method as claimed in any one of claims 81,
82 or 83, wherein the crop area contains cotton plants.
44

Description

!f 3
~ 2 -
The present in~e~tion iB concerned with preparations~or defoliating and/or regulating the growth of plants,
especiall~ ~or the de~oliation o~ plant3, preferabl~ cotton
plants~ compri~ing a compound selected ~rom 1~2~3-thiadla-
zol-5-yl~urea derivatives and 1,2,~-thi~diazolin 2-ld~
deri~ative~ with a b~ically reactive ~ubstance~ and with
the use o~ such preparations.
The term "plant~ u~derstood herel~ to include
trees and shrub~.
1,2,~-~hiadiazol-5-yl-urea derivatives and 1,2,3-
thiadlazolin-2-ide derivative~ have already become known
as agents ~or the defoliation of plants (German Of~enle-
gung6schrift ~o. 2506690; German O~fenleg~gs~chrift ~oO
2619861; German O~enlegung~chrift ~o. 2719810)~ The~e
active ~ubstances arc not, however, ~uf~iciently e~Yect~ve
in all case~0
Mixtures oi 1,2~3-thiadiszol-5-yl-urea deriYatives
w~th other de~oliating age~ts are also already know~ in
which the ~ubstances, which, ~ se, already have a more
or less ~trong de~oliating action, are mutually pot~ntiat-
ing in their action (Germa~ Offenlegungsschrift ~o. 2646712).
~he synergi~tic~action of the~e m;~tures i~ there~ore de-
pendent on two compounds tha~ are already acti~e~
~he aim upon which the present invention iB based has
therefore been to pro~ide an age~t especially for the
deioIiation of plant87 in which the action o~ the 1~273-
thiadiazol~5-yl-urea deri~ative~ or 19 2,~-thiadiazoli n-2-
ide dsrivati~e~ already known to be active is increa6ed by
.

the additi~n of sub~tanc~s that ~Xe, ~ se, inactive as
~egards a de~oliat~ng and~or ~rowth re~ulatin~ action.
Th~s aim is achieved h~ the present invention.
The present invention accordl.ngly provides a
preparation -Eor defoliating and/or regulating the growth
of plants, which comprises a defoliating and/or growth-
regulating compound selected from 1,2,3-thiadiazol-5-yl-
urea deri.vatives and 1,2,3-thiadiazolin-2-ide derivatives,
in admixture or con~unction with a basi.cally reactive
substance.
The present invention also provides a method of
defoliating and/or regulating the growth of a living plant,
wherein the living plant is treated with a mixture compris-
ing (i) a defoliating and/or growth-regulating compound
selected from 1,2,3-thiadiazol-5-yl-urea derivatives and
1,2,3-thiadiazolin-2-ide derivatives and (ii) a basically
reactive substance.
The present invention further provides a method of
defoliating and/or regulating the growth of plants in
a crop area, wherein the crop area is treated with a mixture
comprising (i) a defoliating and/or growth-regulating com-
pound selected from l,2,3-thiadiazol-5-yl-urea derivatives
and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basi-
cally reactive substance.
The preparations of the present invention may be
in the form of concentrates ~hich on dilution provide
mixtures suitable ~or the methods of the present invention.
There is a~so included within the scope of the present
~.~

invention a paek which comprise~ a preparation of the
presen~ invention, together with instruction~ for its u~e
~or defoliat~ng and/or regulating the growth of li~ing
plant~.
According to the pre~ent in~ention -there come into
consideration a~ the compounds having a de~oliating and/or
growth-regulating action:
A) 1,2,3~hiadiazol-5-yl-urea der~vative~ o~ the general
formula I
~ C - H
~ S ~ I \ ~2 (I~
in which
Rl repre~ents a hydrogen atom or a Cl-C5-alkyl group,
R2 represent~ a Cl-C5-alkyl group, a ~5-a~cycloaIkyl
group, a phen~l, halogenated phenyly ~l-C4-~lkyl
~ 15 phenyl~ Cl-C4-alkog~phenyl, nitrophenyl or tri-
; n uoromethylphe~yl group~ an unsubstituted pyridyl
or pyri~idyl group or B pyrid~l or pyrimidyl group
substituted b~ one or more sub~tituents (which may
be the same or dif~erent) selectea ~rom ~1-C4~al~yl
group~ C4-aIko~y group~, halogen atom~ nitro
: group~ and tri~luoromethyl group8 ~

~ S~ ~3
or Rl and R2 together with the ad~acent nitrogen atom
repre~ent ~ morpholino, piperidino or pyrrolid~no
group~
R3 repre~enta a hydro~en ato~ or a C L_C5~a1kY1 grou~
and
X repre~ents an oxygen or ~ulphur a-tom; and
B) 1,2~3-thiadiazolin-2-ide deri~atlves of the genaral
formula II
N Cl X
~ ¦ ~ c = ~ - a _ ~ B ~ (II)
\R2
in which
represents a hydrogen atom or a Cl-C5-alkyl group,
R2 repreaents a hydroge~ atom, a Cl-C5-alkyl grOUpJ a
C5-C8-cycl~alkyl group, a phenyl, halogenated phenyl,
Cl-C4~alk~1phenyl, Cl-04-alkoxyphenyl, nitr~phenyl
or ~ri~luoromethylphenyl group3 an unsub~tituted
pyridyl or pyrimidyl group or a pyrid~l or pyrimidyl
group sub~tituted by one or more substituents (which
- ma~ be~he same or diiferent) selected ~rom Cl-C4-
alkyl groups~ Cl-C4-alkoxy group~, halogen atom~,
nitro grOUp8 and tri~luoromethyl group8 t or
R1 and ~ together with the ad~acent nitrogen atom repre-
~ent a morpholino, piperidino or pyrrolidino ~roup,

~ 6 --
B represents an alkal~ metal atom9 pre~erably a
lithium, sodium or pota~ium atom, o.r a monovalent
; eq~valent of ~inc, manganese 9 calc~um3 magne~ium
or ~arium, and
~ represent~ an oxygen or sulphur atom.
As compound~ o~ the general ~ormula I there may be
mentioned, ~or e~ample, ~he compound~ ted in the iollow-
: ing Table 1.
l-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea
1-Phenyl-l-methyl-3-(1,2,3-thiadiazol--5-yl)-urea
1-(4-Chlorophenyl)-3- ~ 1 9 2,3-thiadia~ol-5-yl~-urea
l-Cyclohexyl-3-(1,?,3-th1adiazol-5-yl)-ures
-Chlorophenyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(4~Methylphenyl)-3~(1,2,~-thiadiazol-5-yl3 urea
1-~3~-Methylphe~yl)-3-(192,3-thiad~azol~5-yl)-urea
1-(3,4-Dichlorophenyl) 3-(1,2,3-thiadiazol-5-yl)-urea
l-~ethyl-~-(1,2,3-thiadiazol-5-yl)-urea
1,1-Dimethyl-~-(1,2,3-thladiazol-5-yl~-urea
~ Dimethyl-~-meth~1-3 (1,2,3-thiadiazol-5-yl)-urea
: 20 1-Methyl-~-methyl-3-(lf2,~-thiadiazol-5-~1)-urea
l-Phenyl-~ ~1,2,3-thiadiazol-5~yl)-~hiourea
1-(4-Chlorophenyl)-3-(1,2 J 3-thiadiazol-5-yl)~thiourea
1-(2 Pyridyl)-3-(1,2,~-thiadiazol-5-yl) urea
1 (5-Chloro-2-pyrldy lp2~3-thiadiazo~-5-yl~ urea
1-(4-Methyl-2-pyridyl~-3-(1,2p~ thi~diazol-5~yl~-urea
1-(4-~ethyl-~-pyr~m1dyl)-~-(1,2,~-thiadiazol-5-yl)-urea
- , .
. .

~t~5
-- 7 --
1-(4-Pyridyl~-3-(1,2~3~thiadiazol-5-yl~-urea
1-(3-Pyridyl~-3-~1,2,3-thiadiazol-5 ~ urea
1~(2 ~yr~midyl~-~-(1,2,3-thiadiazol-5-yl.)-urea
1-(3-Meth~ 2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1-(5-Methyl 2~pyridyl)~-(172,3-thiadiazol~5-yl)-~rea
1-(6-Methyl-2-pyridyl)-3~(1,2,3-thiadiazol-5-yl3~urea.
~ compound~ of the general ~ormula II there may be
mentio~ed; for example, the compound~ ted in the ~ollow-
ing ~able 2.
Table 2
5-tPhenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
sodium salt ~H20
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide,
calcium salt x8H20
5-(Phenylcarbamoylimino3-1,2~3-thiadiazolin-2-ide,
potassium salt ~2
5-(Phenylcarbamoylimino~-1,2,3-thtadiazolin-2-ide;
lithium 3alt ~4~2
5-(Methylphe~ylcarbamoylimino)-1,2,3-thiad~azolin-2~ide,
~odium salt ~2
5(Methylphenylcarbamoylimino) 1,2,3-thiadiazolin-2~ide,
potassium salt ~H20
5-(Methylphenylcar~amoylimino~-1,2,~-thiadiazolin-2~ide,
lithium salt xH20
5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazoli~-2-ide,
sodium salt ~1.5 H20
5-(2-Pyridylcarbamoylimino~-1,2,3-thiaaiazolin-2-ide,
potas~iu~ salt x~20
5-(2-Pyridylcarbamoylimino~1,2,~-thiadiazolin-2~ide 9
lithium salt ~E20
5-(Phen~lthiocarbamoylimino)-1~2~ hiadiazolin-2 ide,
~odium ~alt Z~2

-- 8 --
5 (Phenylcarbamoylimi.no)-1~2,~-thladia~olin-2-ide,
magne~ium salt x2H20
5-(Phenylcarbamoylimino)-1~2,3-thiadiaæolin-2~ide~
zinc salt x3~20
5-(Phenylcarbamoylimino)~1,2,3-thiadiazolin 2-ide~
manganese salt ~3H20
5-(Phenylcarbamoyliminoj~lJ2~-thiadia~olin-2-ide,
barium salt ~2
0~ the~e compound~, the ~ollowi~g are especially
su1table *or the preparatio~s and methods o~ the present
invention:
l-phenyl-~-(1,2,3-thiadiaæol-5-yl)-urea,
l-phenyl-l~methyl-~-(1,2,~-thiadiazol.-5-yl~urea~
1-(2-pyr~dyl) ~-~1,2,3 thiadiazol~5-yl)-urea and
5-(phenylcarbamoylimino)-1,2 9 ~-thiadiazolin-2-ide salt~,
for e~ample -the calcium~ magnesium and mangane~e 8alt8~
The following may be mentioned a~ ~ubstances not, on
their own, ha~ing any defoliating and~or growth-regulating
activity, but bei~g ~uitable a~ the basically reactive subw
6tances ~or the preparation~ and ~ethods vf the pr~ent
~nvention:
alkali h~droxides~ for ex~mple sodium and potas~ium hydroxide~
amine~, ~or example alkylamines~ for e~æmple triethylamine,
alkanolamlne3, for example diethanolamine, triethanolamine
and triisopropanolamine 7 and hexamethylenetetra~ine~
carbonate~ 7 for example sodium carbonate, potassium car-
bonate and ammonium carbonate,
phosphates, ~or example tertiary pho~phates, for example
trisodium phosphate and tripota~sium phosphate 7 and pyro

- 9 -
pho~phates, ~or example tetrasodium pyrophosphate and
-tetrapotassium pyrophosphate,
alkali salt~ o~ mo_ carbox~lic acids, ~or example sodium
I oleate.
It is preferable to u~a basically reactive substance~
that adjust the preparations of the present invention and
the mi~ture~ used in the methods of the precent invention
to a p~-value o~ more than 8, pre~erably within the range
: of ~rom 9.5 to 11.5.
Surprisingly, the mixture~ of the defoliating and/or
growth-regulatin.g compounds and the basically reactive
sub~tances when u~ed according to the present ~nventlon
have an act~on that i~ greater than that of the individual
components. ~he~ are therefore especially suitable for
the de~oliatio~ o~ cotton plants whereby, in an ideal
manner, the use o~ picking machines for boll harvesting
i~ rendered pos~ible.
Other plant~ can, however, also be advantageousl~
defoliated a~d/or in~luenced in their growth, as example~
o~ which there may be mentioned the promotion of bushiness 7 .
for~ation of ~ide-ahQots~ and ;nhibition o~ root growth i~
the case o~ grasse and dicotyleaons, ~or example hibiscu~,
apple tree3 and other woody plant~. ~here~ore the prepara-
tions according to the present invention can be used adva~-
tageou~ly both ~or defoliating plant~ and al~o for regulat-
ing their growth~
; It i~ known to the man sk~lled i~ the art that

defoliation i~ not a herbicidal action and that it i9 not
desired actually tG kill the tre~ted plànts because the
leaves still remain a-ttached to the dead plant~ and the
productive parts o~ the plant can be damaged. ~he aim oP
de*oliation, that iY to facilitate harve~ting and to obtain
a purer harvested cropf can be 108t as a re~ult o~ this.
It i9 there~ore necessary ~or the plant~ to remain alive
while the leaves are becoming detaehed and falli.~g of~,
Thi~ permits the further development o~ the productive part~
of the plant while the re-growth of new leave~ i~ prevented.
The mixtures u~ed in accordance with the present invention
achieve all thase aims in an advantageous manner 80 that it
can be assumed that the prior art is far e~ceeded~
~he mixt~re v~ the defoliating and/or growth-regulating
compound and the basically reactive substance i~ accordance
with the present in~ention can also be u~ed i~ admixture
with other active substa~ces 9 ~or example de~oliating agent~,
plant-protecting agents and/or pesticide~ depending on the
: desired purp~e. Thus, the preparations o~ the present
in~ention may contain such further active substance~.
The action and the speed o~ action can also be promoted,
~or e~ample by actio~-increasing additive~, for example
organic solvents~ wetting agents and oils. Thi~ permit~
a ~urther decrease in the quantity of the ac~ual activ~
substance~ u~ed.
The mi~ture o~ the de~oliating andjor growth-regulat-
ing compound and the basically reactive ~ubstance in

3 ~
accordance with the prQsent invention i.9 advantageousl~
used ~n the *orm o~ preparations, for e~ample powder~,
strewable preparations, solution~, emulsio~s or ~uspension~,
with the addition o~ liquld and/or solid carrier~ or
diluents and, i~ de~ired, of surface-ac:tive agents, ~or
example wetting, adhesive, emulsi~yi~g and/or di~persing
; agent~.
Suitable liquid carriers are, ~or e~ample, water,
aliphatic and aromatic hydrocarhons, for example benzene,
toluene and ~ylene 9 cyclohexanone, isophorone, dimethyl
; sulphoxide, dimethyl~ormamidel and also mineral oil
fraction~.
Suitable ~olid carriers are, for egample, mineral
- earths, for example tons;l~ silica gel, talcum~ kaolin,
. 15 attacla~, lime~tone and ~ilicic acid 9 and vegetable pro-
ducts, ~or example meals.
I AB surface-active agent~ there may be mentloned, ~or
example~ sodium or calcium lignin ~ulphonate, polyo~yethy-
len~$~kylphen~1 ethers, naphthalenesulphonic ac~ds and
~alts thereo~, phenolsulphonic acids and salts thereof,
~ formalde~yde conde~sates, ~atty alcohol sulphates, salts
', ~f long-chained ~atty acids and al90 sub~titu~ed benzene-
sulphonic acids and salts thersof.
The proportion of t.he e~sential constituent~, namely
the defoliating and/or growth-regulating compound and the
ba~ically reactive substance, in the various preparations
msy vary within wide limits. ~or e~ample, the preparations

3~ G~
of the present inventlon and the mixture~ used in the
methods o~ the present invention may co~tain approximately
from 5 to 95~ by weight o~ these consti~uents, approximately
~rom 95 to 5~ by weight o~ liquid and~or sol~d car~ier(~)
and al90~ i~ de~ired, up to ~O~o by weight of s~r~ace-aotive
agent(s).
~ he relative ratio by weight o~ the es~ential co~-
st~tuent~ in the variou~ preparations i~ advanta~eou~l~
appro~imately 1 part by weight of the compound having a
lV defoliating and/or growth-regulating action to 0.5 to 1000
parts by weight o~ the ba~ical~y reactive substance~ and
depends on the sensitivity and resistance of the plant~,
the time of application, the climPtic condition~ and the
~oil conditions.
~he quantitie~ applied of the mixture o~ the de~oliat-
ing and/or growth-regulating compound and the basically
reactive ~ubstance for the desired de~oliatio~ and~or gro~t~
regulating action are generally within the r3nge of rom
1 to 10~000 g per hectare, preferably ~rom 10 to 1000 g
per hectare.
The mixture oX the de~oliating and/or growth regulat-
ing compound an~ the basically reactive substance may be
applied in the conventio~al manner, for e~ample with water
as the carrier, in quantities of ~pray liquor o~ approxi-
mately from 100 to 1000 litres/hectare. It is alsopossi~le to apply t~ese mi~tures by the so-called "low-
volume" or "~ltra~low-volume" method.
~ he compounds having a defoliating and/or growth-

i'3~
- 13 -
regulating action and the ba~ic additives contained in the
preparations of the pre~en-t invention and in the m~xture~
used in the methoda of the present invention are known
se and may be manufactured according to method~ known
per se.
For the manufacture`o~ the preparatio~s o~ the pre~ent
invention) there may be used, for example~ the con~tituent~
li~ted under a~, b), c) or d) i~ the follo~ing Table ~ -the
mixture in each caee oi cour~e referring to the mixture oi
the defoliating andlor gro~th-regulating compolund and the
ba~ically reactive substance,
Table
a) 95 ~ bg weight o~ mixtuxe
4 ~ by weight of kaolin
1 ~ by weight of sur~ce-active agent~ ba~elon ~he
- ~odium aalt of ~-meth~ Qleyl~ta~r ~
and the calcium ~alt of lignin sulphonr
ic acid
b) 80 ~ by weight of mixture
- 10 % by weight o~ calcium ~alt o~ lignin ~ulphonic acid
% by weight of ammonium ~alt of the monosulphuric
acid e~ter o~ tetraethylene glycol
nonyl phenyl ether
7 ~ by weight o~ colloidàl eilicic acid
c) 20 ~ by weight of Mi~t~re
70 ~ by weight of ton~il
8 ~ b~ weight o~ celluloae pitch
2 % by weight of wetting agent based on a ~atty acid

- 14 -
conde~sation prod~ct
d) 5 ~ by weight o~ mi~ture
80 ~ by weight of ton3il
~ 10 ~o by weight o~ cellulo~e pitch
i 5 5 % by weight o~ wetting agent based on a fatty acid
condensation prod.uct
The preparations o~ the present lnvention are
manufactùred, ~or example, bg mixing the individual co~
stitue~t~ i~ a drum and then gri~di~g i~ a mill.
These preparations may be applied either direct~y or
a~ter dilution with water to the plants to ~e treated~
The p~-value of the~e preparations is of special importance
for potentiating the action of the esse~tial compo~ents a~d
should advantageously be greater tha~ 8, pre~erably within
the range o~ from 9.5 to llo 5. It thus represents a
special embodiment o~ the present invention.
~ he ~ollowing Examplee illustrate the inventio~. The
E~amples are based on greenhou~e test~ that were generally
carried out on cotton plant~ hav~ng ~rom 5 to 8 true ~oliage
20 leavesO The mixtures of tke defol~ating and~or growth-
: regulating compound and the basicall~ reactive substa~ce
were applied in the ~orm o~ ~queous preparations ba~ed on
the compo~ition~ described abo~e~
The test~ i~ E~a~ples 1 to 13 were evaluated by count-
ing the number Q~ leave~ shed after the application and bycalculating the proportio~ as a percentage of the total
~umber o~ leave~. In the individual tests~ the ~ame number

- 15 -
of lea~e~ was alwaye available per test member. The number
o~ leave~ per te~t member var~ed from te~t to test between
20 and 28 ~oliage leave~ per test member.
The following EY.amples 1 to 13 contain information on
the active substance, basically reactive ~ub~tance, mixture,
quantity applied, and the percentage de~oliation determined.
In some case~ there i~ ~ndicated in brackete a~ter the per-
centage de~oliation obtained bg the combinations, the value
calculated according to the method de~cribed by S.R~ Colby
which would be expected in the case o~ an additive action
[~.R. Colby "Calculating Synergistic and ~ntagonistic
Re~ponses o~ ~erbicide Combinatio~" Weed~ 15/1 (1967)
pO 20-22].
This calculation wa~ ~ade according to the follo~ing
equation:
100
in which X = percentage defoliatio~ with substance A u~i~g
p kg o~ active sub~ta~ce/ha
Y = percentage defoliatio~ with ~ubstance B u~i~g
q kg o~ active ~ub~tance/ha
E = e~pected de~oliation bg A + B u8ing p + ~ kg/ha
If the value observed iB greater than the value ~
calculated accordi~g to Colby then the combi~ation ha~ a
~ynergi~tic action. The re~ults of Example~ 1 to 13 clearly
show the potentiatio~ o~ ac~ion of the sub~tance having a
de~oliating action b~ the bas~cally reacti~e ~ub~tances
that are them~elves inactive as de~oliantsJ

- 16 -
Example~l
Young cotton plants at the stage oi ha~ng 5 folia~e
leaYes were treated in a series of test~ with the mi~ture~
indicated in the ~able belo~ and ulth the individual com-
ponents of the m~xtures, namely the acti~e substance andthe basically reactive ~ub~tance (repeated 4 time3)~ The
: qua~tity oi water used a~ c~rrier was 500 litres/ha~
~ter a ~ew day~ the percentage o~ shed leave~ wa~ deter
mined. ~he results are given in the followi~g ~able:
10 Components Application Defoliation E
quantity a~ a ~ (according
in g / ha to Colby)
l-phenyl~ (1,2 380 35
thiadiazol-5-yl5-
1~ urea = I
~C0~ = II 500 0
E4 27 5
I ~ II 80 + 500 70 (35~
i I ~ III 80 ~ 500 60 (35)
Exam~le 2
Young cotton plants were treated a~ indicated in
3~ample 1. The re9ult8 are given in the following ~able~
Component~ Applica~io~ De~ol~atio~
quantity a~ a ~ (accQrding
in g / ha to Colby)
l-phenyl-3-~1,2 ~- 80 57
thiadiazol-5 yl5-
urea = I
2C~3 _ II 50~ 0
.
1:

' DiJt
- 17 ~
Component~ Application. Defoliation
quantity aY a ~ (according
n g / ha ~ to Colby~
2C3 = XV 500 C)
(NE4)2C3 = IV 500 0
~OE - V 500 O
I + II 80 + 500 70 (57)
I ~ XV 80 + 500 85 (57)
I ~ IV 80 + 500 80 (57)
10I + V 80 + 500 60 (573
~amPIe ~
Young cotton plants were treated ~ indicated in
~xample lo The re~ult~ are given iQ the following Table.
Component~ Appl~cation Degoliation :E:
15quantity as a ~ (according
In g / ha to Colb~)
I
¦ l-phenyl-3-(1,2 ~- 40 29
thiadiazol-5-yl~-
urea = I
1 20 Na olea~e = VI 500 0
! triethanolamine = YII 500 o
triethylamine = VIII 500 0
I + VI 40 ~ 500 33 (29 ?
VII 40 ~ 50043 (29)
X ~ VIII 40 ~ 500 62 (29)
xample ~
Toung oott~r plants were treated aa indioated in
"
.

L ~ ~3 ~
_ 18 ~
Example 1~ The lower percentage action compared with
the above Example~ can be attributed to~ unfavourable
environmental conditions when the test~ were carried out
in the winter months. The results are given in the
*ollowing Table.
Component~ Application Defoliation
quantity as a
i~ g / ha
l-phenyl-3 (1,2 3- 80 0
thiadiaæol-5_yl~_
urea = I
~2co = II 500 0
19000
I + II 80 + 500 29
5-(phen~l- 80 0
carbamoylimino)
19 2,3-
thiadiazolin~2-
ide,
calcium ~alt - IX
IX + II 80 + 500 24
1-~2-pyridyl)- 80 0
3-(1,2,3-
thiadiazol-5 ~1)-
urea = X
X + II 80 ~ 500 23.5
Young ~otton plant~ were treated a~ indicated in
Example 4~ The re~ults_are given in the following Table.

-- 19 --
Component~ Application De~oli~tion E
quantity as a ~ (accordin~
in g / ha ~ to Colby)
5-(phenylcarbamo~l- 500 17
, 5 imino~ 2,3-
i thiadiazolin~2-~de,
potassium salt - XI
E~C03 = II 500 0
XI ~ II 500 + 500 39 (17)
i
xam~le 6
I Young hibi~cu~ plants each havlng ~om 7 to 10 un-
~olded lea~e~ were treated as indicated in Example 1~
The percentage o~ shed leaves wao determined 6 day~ aXter
the treatment~
.
!
15 ~omponent~ ~pplication De~oliation
quantit~ a~ a % (according
in g / h~ to Colby)
l-phenyl ~-(1 t 2 3- 2.5 0
I thiadiazol~5~yl~ 10 4
. 20 urea = I
I E C0 = II 500 0
! 2 3
E4P207 = III 500
I ~ II 2.5 ~ 500 14 (0)
10 ~ 500 46 (4)
25I ~ III 2.5 ~ 500 11 (0~
10 + 500 54 ~4)
~1
Youn~ cotton plants were treated a~ indicated ~n
1. ' .

~ 20 -
Example 1. The ~e~ult8 are given in the ~ollowi~g ~able.
Component~ ~pplication Defoliation
- quantit~ as a ~ (according
in g / ha to Colby~
1-phenyl-3
, (1,2,~-
thiadiazol-5-yl)-
urea = I 40 19
C0~ 000 0
10 E4P27 = III~000 0
I ~ II 40 + 300 57 (19)
40 + 1000 67 ~lg~
40 + 3000 71 ~19)
40 ~10000 76 (lg)
I f III 40 + 1000 62 ~19)
40 ~ ~000 ~6 (19)
~ A 40 ~10000 90 ~19)
.
Example 8
Young cotto~ plant~ were treated as indicated
~ample 1. The result~ are given in the ~ollowing Table~
I ~omponent~ Applicatio~ ~efoliation ~
I quantity as a % (accord mg
in g / ha to Colby)
l-pheny1-3~ 40 ~3
25 (1?2~
thiadiazol-5-yl)-
urea = I
~j E2C3 = II 540 0

21
Components Application De~oliation ~
~uantity a~ a ~ (acoording
in g / ha ~ -to Colb~)
hexamethyl~ne- .
5 tetramine = XVI 540
I ~ II4 ~ 500 71 (~3)
I t XYI40 + 500 48 (33~
~2 .
Young ootto~ plants were treated as indicated i~
Example 1. The re~ults are giva~ in the following Table~
Components Application Defoliation E
quantity a~ a ~ (according
in g / ha to Colby~
l-phenyl-3- 4Q 64
tl,293-
thiadiazol-5-yi)-
urea. _ I
E2~03 = II 500 0
E3P04 = XYII 500 0
I + II40 -~ 500 86 (64)
I + ~VII 40 + 500 91 (64
Young cotton plants wer~ treated as indicated in
~ample 1. ~he re~ults are gi~en in the ~ollowing TableO

t~
_ 22 -
Componenta ~pplication Defoliation ~
qua~tit~ as a % (according
~n g / ha ~ to Colby)
__ ~_ ___
1 phenyl-l-methyl~ 4 63
5 3~(1 2 9 3-thiadlazol-
5-yl~-urea - XII
C0~ = II 500 0
po4 = XVII 500
XII ~ II 40 -~ 500 71 (6~)
XII + XVII 40 + 50 76 t6~)
:E~amPlQ 11
Young cotton plant~ were treated as indicated in
E~ample 1. The re~ults are g.iven in the following Table~
Component~ Ap~llcatio~ Defoliation ~
. quantity as a % (according
i~ g / ha to Colby)
5 (phenylcarbamoyl 40 52
imino)-1,2,~-
thiadiazolin-2-ide,
magnesium ~alt = XIII
E3P04 _ XVII 500 0
~XII + XYII 40 ~ 500 71 (52)
Example_12
~oung cotton plants were treated as ind~cated i~
~xample 1. The results are gi~en in the iollowing Table.

~ 2
Components ~ppli.cation Defoliation ~
quantlt~ a~ a ~ (accordi~g
in g / ha ~ to Colb~
5-(phenylcarbamo~l-
5 imino)-1~2j3
thiadiazolin-2. -ide t
ma~ganese ~alt = XIV 40 32
P04 ~ XVII 500
XIV + XVII40 + 500 82 (~2)
am~le l~
Young cotton plants having ~rom 21 to 27 leave~ were
treated as indicated in Example 1~ The results are given
in the following Ta~le.
Components Application Defoliation
quantit~ as a
in g / ha
l-pheny1-3-
(1,2 3-thiadiazol-
5-yl~-urea = I 300 19
2 3 = II 1000 . 0
I + II~00 ~ 1000 48
xam~le 14
In a ~eries of tests youn~ Urtica urens plant~ ~ere
sprayed with the mi~ture according to the present invention
indicated in the Table below and with the individual com-
ponent~ of the mi~tureO Three weeks later the fresh weight
o~ the part0 o~ the plant~ above the ~oil wa~ determinedO
The ~ollowi~g Table give~ the relative values for plant
.
.

- 24 -
height and the ~resh weight (untreated = 100)~ A~ compared
with the untreated control plants, the treated plant~ had
the desired more compact, lower and therefore more stable
growth~ ~heir fresh weight was nevertheless greater. The
results o~ the tests ~how that the mi~ture according to
the present i~vention brin~ about a greater growth~regu~
lating action than the individual components.
: Component3 Application Relativ~ Relative
! concentration plant fresh
in ppm height weight
l-phenyl-3- 2 79 :L13
(1,2,3
thiadiazol-5-yl)-
urea _ I
E2CO~ = II 26 100 100
I + II 2 + 26 75 1~1