LU83705A1 - MEANS, IN PARTICULAR, FOR THE DEBELING OF PLANTS - Google Patents

Description

»<*

SCHERING AG

Intellectual Property Law Berlin, August 28, 1981

AGENTS, IN PARTICULAR, FOR THE DEFLURING OF PLANTS

The invention relates to an agent in particular for defoliation of plants, preferably cotton plants, containing mixtures of 1,2,3-thiadiazol-5-ylurea or 1,2,3-thiadiazolin-2-id derivatives with basic reacting substances.

1,2,3-thiadiazol-5-yl-urea and 1,2,3-thiadiazolin-2-id derivatives have already become known as agents for defoliation of plants (DE-OS 25o669oj DE-OS 261986I; DE- OS 27198I0). However, these active substances do not show sufficient effects in all cases.

Mixtures of 1,2,3-thiadiazol-5-yl-urea derivatives with other defoliation agents are also known, in which the substances which have a more or less defoliation effect potentiate each other in their action (DE- OS 2646712). The synergistic effect of these mixtures is therefore dependent on two already active compounds.

The object of the present invention is therefore to provide an agent, in particular for the defoliation of plants, in which the action of the 1,2,3-thiadiazol-5-ylurea- or 1,2,3-thiadiazolin-2-id known as effective -derivatives is increased by the addition of ineffective substances.

/ '2 ~

U

m s t—. · J. Π. U..kAr (A.nia. Br rkriafUn Drtihn. Uan · - Inrnan UimeRfl Dnc * anerlirift · Aß. ΒαρΙΙπ R * \. Pri <ffarfl

SCHERING AG

/ “Intellectual Property Law r»

This object is achieved according to the invention by an agent which is characterized by a content of a defolating 1,2,3-thiadiazol-5-yl-ha * 'nstoff- or 1,2,3-thiadiazolin-2-id- derivative in a mixture with a basic reacting substance.

Suitable defolishing compounds according to the invention are: A) 1,2,3-thiadiazol-5-yl-urea derivatives of the general formula

N-C - H

X Rn t! / 1

; N C - N - C - N I

\ / I \ S R3 H2 in the R_ hydrogen or a CC - alkyl radical, R0 a C ^ -C ^ allcyl radical, a C ^ -Co-cycloallcyl radical, a phenyl, halophenyl, C ^ -C ^ alkylphenyl -, C ^ -C ^ alkoxyphenyl, nitrophenyl or trifluoromethylphenyl radical, an unsubstituted or one or more identical or different by C ^ -C ^ alkyl radicals, C ^ -C ^ alkoxy radicals, halogen atoms, the nitro group or Trifluoromethyl group substituted pyridyl or pyrimidyl radical or R ^ and R ^ together with the N atom, the morpholino, piperidino or pyrro-1 idino group, R ^ hydrogen · or, a C ^ -C ^ alkyl radical and / '3' io - m à ^ r T ~ 2 Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jörgen Hamann Postal address: SCHERINQ AS D-1000 Berlin 65Postbox 650311

-3- SCHERING AG

f **

Intellectual Property Law X represents an oxygen or sulfur atom; B) 1,2,3-TiIIadiazolin-2-id derivatives of the general formula

H

® 'w =. çf

ι ι ï A

N C = N - C - N B II

\ / h 'S 2 in which% R_ is hydrogen or a C -C alkyl radical, R0 is hydrogen 1 ± p ^ or a C, -C "alkyl radical is a C_C0 cycloalkyl radical, one; 1 p ’'5 υ

Phenyl, halophenyl, C ^ -C ^ alkylphenyl, C ^ -C ^ alkoxyphenyl, nitrophenyl or trifluoromethylphenyl, an unsubstituted or one or more of the same or different by C ^ -C ^ - Allyl radical, C ^ -C ^ alkoxy radicals, halogen atoms, the nitro group or the trifluoromethyl group substituted pyridyl or pyrinidyl radical: or and R0 together with the N atom mean the morpholino, piperidino or pyrrolidino group and B is an alkali metal atom, preferably a - Lithium, sodium or potassium atom, or a corresponding equivalent of a zinc, manganese, calcium, magnesium or barium atom and X represent oxygen or sulfur.

Examples of substances of the general formula I which may be mentioned are: l-phenyl-3- (1,2,3-thiadiazol-5-yl) -urea l-phenyl-l-methyl-3- (1,2,3-thiadiazole- 5-yl) urea> eä cn · »

T-I

J λ / arxtanei * Dr *. Herbert. Dr_ Chfistrün Bruhn. Hdmann Pösianefihriif * SCHPRINfi Afn «Π.1 (5 / Υ1 Berlin ftK. BncHant, m h

, 4th SCHERING AG

Commercial legal protection 1- (4-chlorophenyl) -3- (l, 2,3-thiadiazol-5-yl) urea l-Cycloaexyl-3- (l, 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-3-yl) urea 1 - (3-methylphenyl) -3- (1,2,3-thiadiazol-5-yl) urea 1- (3, ^ - dichiorphenyl) -3- (1,2,3-thiadiazol-5-yl) - urea l-methyl-3- (l, 2,3-thiadiazol-5-yl) urea 1.1-dimethyl-3- (1,2,3-thiadiazol-5-yl) urea 1.1-dimethyl-3-raethyl -3- (1,2,3-thiadiazol-5-yl) urea l-ethyl-3-raethyl-3- (l, 2,3-thiadiazol-5-yl) urea l-phenyl-3- ( 1,2,3-thiadiazol-5-yl) -tniourea 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- (l, 2,3-thiadiazol-5-yl) urea 1 - ((t-methyl- 2-pyridyl) - 3- (1,2,3-thiadiazol-p-yl) urea 1- (4-methyl-2-pyrimidyl) -3- (1,2,3-thiadiazol-5 ~ yl) - urea 1 - ((t-pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea 1- (3-pyridyl) -3- (1,2,3-thiadiazol-5-yl) -urea 1- (2-pyrinidyl) -3- (1,2,3-thiadiazol-5-yl) urea 1- (3-2iethyl-2-pyridyl) -3- (l, 2,3-thiadiazol-5 ~ yl) urea 1- (5-methyl-2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) urea 1- (6-methyl-2-pyridyl) -3- (1, 2,3-thiad ± azol-5-yl) urea.

'L · -5- m a en -τ

_5_ SCHERING AG

Commercial law enforcement

Examples of substances of the general formula II are: 5 - ’(PLenylcarbanioylinino) -1,2,3-thiadiazolin-2-id,

Sodium salt nHo0 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Calcium as xoHqO

5- (phenylcarbanoylinino) -1,2,3-thiadiazolin-2-id,

Potassium salt xH „0 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Lithium salt x4Ho0

Cd 5- (methylplienylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Sodium salt χΙϊ ,, Ο

Cd 5- (methylphenylcarbamoylinino) -1,2,3-thiadiazolin-2-id,

; Potassium salt xH ^ O

5- (methylplienylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Lithium salt xH ^ O

5- (2-pyridylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Sodium salt xl, 5 Ho0 5- (2-pyridylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Potassium salt xîïpO

5- (2-pyridylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Lithium salt xH ^ O

5- (phenylthiocarbamoylmino) -1,2,3-thiadiazolin-2-id,

Sodium salt xli ^ O

5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Magnesium salt x2H90 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Tin salt 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Manganese salt x3Ho0

La 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id,

Barium salt x3HQ0 / · -6- u °? * d »

(O

. · Πγ HArhftft · Hf ^ hrtcfien fllriihn «Inroan Uflnsnn PeefenArhrift · Aß · Sftrlin 11

_e_ SCHERING AG

Intellectual Property

Of these substances, the following are particularly suitable according to the invention: l-phenyl-3_ (1,2,3-thiadiazol-5-yl) urea 1- (2-pyridyl) -3- (1,2,3-thiadiazol-5-yl ) urea 5- (phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id salts.

The following are to be mentioned as substances which are ineffective on their own according to the invention: alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, amines, such as alkylamines, for example triethylamine, alkanolamines, for example diethanolamine, triethanolamine and triisopropanolamine, Hexamethylenetetramine,

Carbonates, such as sodium carbonate, potassium carbonate, ammonium carbonate,

Phosphates, such as tertiary phosphates, for example trisodium phosphate, tripotassium phosphate, pyrophosphates, such as tetra-sodium pyrophosphate or tetrapotassium pyrophosphate, monocarboxylic acid alkali salts, such as sodium oleate.

For this purpose, such substances should preferably be used which bring the agent according to the invention to a pH. Set above 3, preferably from 9.5 b.i-S 11, -5 * -.

The agent according to the invention surprisingly has a knitting that is larger than that of the individual components.

It is therefore particularly suitable for defoliation of m a -,

Board: Dr. Herbert Asmls - Dr.Christian Bruhn - Hans-Jüroen Hamann Psstan «* rif> · srtwpaiNR AR. D.iooo Rariin it. Pnctfarh «ran

_7_ SCHERING AG

' Intellectual Property

Cotton plants, which ideally enables the use of plowing machines for capsule harvesting.

However, other plants can also advantageously be defoliated or their growth can be influenced, such as, for example, encouraging planting, side shoots,

Inhibition of root growth in grasses and dicotyledons, such as hibiscus, apple and other woody plants. It is understood that the agent according to the invention can therefore advantageously be used both for defoliation and for regulating the growth of plants.

It is known to the person skilled in the art that defoliation is not a herbicidal action and that even killing the treated plant is undesirable because the leaves adhere to the killed plant and the productive parts of the plant can be damaged. The purpose of defoliation to make harvesting easier and purer crops

Can be lost. It is therefore necessary to keep the plant alive while the leaves separate and fall off. This enables the further development of the productive plant parts, whereby new leaf growth is to be prevented. The agent according to the invention solves all of these tasks in an excellent manner, so that it can be assumed that the prior art is far exceeded.

-8- n 8 T · έ Board! Dr. Herbert Asmis * Dr. Christian Bruhn - Hans-Jürgen HamanTn Postal address: SCHERING AG «D-1000 Berlin 65 · PO Box 65 0311

.a. SCHERING AG

Intellectual Property

The agent according to the invention can also be used in a mixture with other active ingredients, for example defoliants, pesticides or pesticides, depending on the desired purpose.

Its promotion of the effect and the speed of action can also be achieved, for example, by means of additional additives such as organic solvents, wetting agents and oils. This allows a further reduction in the application rate of the actual active ingredients.

The mixture according to the invention is expediently used in the form of preparations, such as powders, litter, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing agents.

Suitable liquid carriers are, for example, water, * aliphatic and aromatic hydrocarbons, such as benzene,

Toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, and mineral oil fractions.

Mineral soils are suitable as solid carriers, for example Tonsil, silica gel, talc, kaolin, Attaclay, limestone, silica and vegetable products, flour for example.

~ 9 '01 di «n» i Board of Directors: Dr. Herbert AsmisDr. Christian Bruhn * Hans-Jürgen Hamann Postal address: SCHERING AG · D-1000 Berlin 65 «Postfach 65 0311

SCHERING AG

Intellectual Property

Examples of surface-active substances include: sodium or calcium lignin sulfonate, polyoxyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formal dehyde condensates, fatty alcohol sulfates, salts of long-chain fatty acids and substituted benzenesulfonic acids and their salts.

The proportion of the labeled mixture in the various preparations can vary within wide limits. For example, the agents contain about 5 to 95 percent by weight of this mixture, about 95 to 5 percent by weight of permissible or solid carriers and optionally up to 30 percent by weight of surface-active material.

The weight ratio of the components in the mixed mixture should be about 1 part by weight of the defoliant substance to 0.5 to 1000 parts by weight of the inactive, basic substance, and mentions sic .; according to the sensitivity and 'resistance' of the groats, the 'application point, the climatic conditions and soil conditions.

The application rates for the desired defoliation are 1-10 000 g mixture / ha, preferably 10-1000 g mixture / ha.

The application of the agent can be eriol- «à s- * 1 t a. fN- λ .—: ·. λ *. . ui on ·. h'imBn Hamann Postal address: SCHERING AGD-100Ö Berlin 65Pox 65 0311

_10. SCHERING AG

Commercial legal protection, for example with water as a carrier in spray liquor quantities of approximately 100 to 1000 liters / ha. Application of the agents in the so-called "low-volume" or "ultra-low-volvune process" is also possible.

The substances with defoliation and the basic additives of the marked mixture are known as such and can be prepared by processes known per se.

The following constituents are used, for example, to prepare the preparations: a) 95% by weight of mixture 4% by weight of kaolin 1% by weight of surface-active substances based on the sodium salt of N-Merhyi-N-oleyl-taurine and the calcium salt of lignosulfonic acid b) 80% by weight of mixture 10 weight percent calcium salt of lignin stilfonic acid I. 3% by weight ammonium salt of monosulfuric acid; 'esters of Te-crarithylene glycol nonyl phenyl ether 7% by weight colloidal silica c) 20% by weight mixture 70% by weight Tonsil 5% by weight cell pecli 2% by weight wetting agent based on a fatty acid ^ ^ condensation product -11- tn À m À · V—

VnretanW · Π * · U * rhaH Ä <mi <. Plf rmhn. I4an «-.) Itrn * n Uamann e ^ uCBlktft * Λ Π ^ ΛΛΛ ce _ £ CM44

_i; l_ SCHERING AG

Commercial legal protection d) 5% by weight mixture 80% by weight Tonsil 10% by weight cell pitch 5% by weight wetting agent based on a fatty acid condensation product

The preparations are prepared, for example, by mixing the individual components in a drum and then grinding them in a mill.

These preparations can be applied to the plants to be treated either directly or after dilution with water. The pH of these preparations is of particular importance for the potentiation of the action of the mixture and should expediently be greater than 3, preferably from 9.5 to 11.5 " be.

It represents a special embodiment of the invention.

-12- à ▼

SCHERINGAG

" Intellectual Property

The following examples are based on greenhouse tests which were generally carried out on cotton plants with p-oclitn lauo leaves. The agents were used in the form of aqueous preparations based on the compositions divided above.

The tests were evaluated by punching out the leaves thrown off since the application and by calculating the proportion in / «the total number of leaves. The same number of leaves was always available for each "test member". The number of ulauts per test member varied between 20 and 2 years of leaves per test member from test to test.

The examples below contain information on the active substance, the substance with a basic reaction, the mixture, the amount applied and the percentage of defoliation determined. In some cases, behind the percentage of défoliation achieved by the combination in parentheses, the fourth recited by the method described by SRColby is given, which would be expected if additive effects were present (SRColby "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations" Weeds 15 / 1 (1967) p 20-22).

-13- »à * r r“ i Board of Directors: Dr. Herbert AsmisDr. Christian BruhnHans-Jürcen Hamann Postal address: SCHEHING AG0 * 1000 Berlin 65 ♦ Postfa? 65 0311

_13_ SCHERING AG

Intellectual Property

The calculation was based on the following formula: p _ v y 3CY

E - Λ + r “where X = percentage defoliation with

Substance A at p kg active ingredient / ha Y = percentage defoliation with

Substance B at q kg active ingredient / ha E = expected defoliation by A + B at p + q kg / ha

If the observed value is higher than Colby's calculated value E, the combination has a synergistic effect. The results of these examples clearly show the potentiation of the effect of the defoliation-effective substance by the ineffective, basic-reacting substances.

example 1

Young cotton plants in the stage of 5 leaves are treated with the following components of the ^ iti-els, the nominal active ingredient, basic reacting substances and their a-ix loop (repeated 4 times). The amount of water used was 500 ltr / ha. After a few days the percentage of leaves dropped was determined. The results are shown in the following table:

Components application rate defoliation ^ in g / ha in% (n.Colby) l-phenyl-3- (l, 2,3- GO 35 thiadiazol-5-yl) -

urea = I

A

s

Pi di «r

UarU.rf ä · «:. . n. __b ^ .l. u ... ir ... «. U ·. »« · «Each. n_1f ¥ Yl Berlin K. Pn * tfarh MA311

SCHERING AG

" " Intellectual Property

Components application rate. Defoliation E

in g / m $ o · (n * Colby)

Ii "CO II 500 0

KtP „0 = III 500 0 I + II 30 + 500 70 (35) I 4- III CO + 500 60 (35) 3 ice cream 2

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table.

Components application rate defoliation p

in g / ha in iS (n.Colby) l-phenyl-3- (l »2,3- ^ 0 57

thiadiazol-5-yl) urea = I

KoC0 = II 500 0

- J

Na CO = XV 500 0 3 (NII4) oC0 = IV 500 0 K OH = V 500 0 I + II 80 500 70 (57) I 4- p ~ - CO 4- 500 "5 (57) I 4- IV 30 4- 500 30 (57) I 4- V ßo 4- 500 60 (57) "15 ~ * rma * 2 Mind · Rr_ Η · γΚαγ +. ßr_ Christian Bruhn · HaflS-Jüfeên Hamann Postal address »SCHERING AG · 0 * 1000 Berlin fifi · Pnstfarh fi5 03 11

_15_ SCHERING AG

Commercial legal protection

Example 3

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table:

Components application rate defoliation e in g / ha in% (n.Colby) l-phenyl-3- (l, 2,3- 40 29 thiadiazol-5-yl) -

hax-nstoff = I

Na oleate = VI 500 0

Triethanolamine = VII 500 0

Triethylamine = VIII 500 I + VI 4ö * 500 33 (29) I + VII 40 + 500 43 (29) I 4. vill 4 0 + 500 62 (29)

Example 4

Young cotton plants were treated as indicated in Example 1. The lower efficacy percentages compared to the previous examples are due to unfavorable environmental conditions during the experiment in the winter months. The results are shown in the following table.

Components Application rate defoliation _ in g / ha_in% _ l-phenyl-3- (l, 2,3-80 0 thiadiazol-5-yl) - urea = I -l6- ls \ A / 1 8 L · · Π »A λ mim. .η Β ·.> | ·>. U «rtC. ΙΓιΜΜ Uama / lfl · C / ^ UCOIU / Î ΑΛ - Π_1ΠίΥ) D «rlin CC _ CC / M14

_l6_ SCHERING AG

Intellectual Property

Components on low deflowering in g / ha in 500 0 K2C03 = 11 1,000 0 I + II 80 + 500 29 5- (phenyl-30 0 carbamovlimino) - 1,2,3-thiadiazolin-2-id ,

Calcium salt = IX

IX + II CO +500 2k 1- (2-pyridyl) - SO 0

3- (1,2,3-thiadiazol-5-yl) urea = X

X + II 30 + 500 23.5

Example 5

Young cotton plants were treated as indicated in example -i. The results are shown in the following table.

Components Application rate Entolattering Λ in g / ha in fr (n.Colby) 5- (phenylcarbamoyl- 500 1f imino) -1,2,3- thiadiazolin-2-id,

Potassium salt XI

K2co3 = II 500 0 XI + II 500 + 500 39 (17) ms

SCHERING AG

Intellectual Property

Example 6

Young hibiscus plants with 7-10 leaves each were treated as described in Example 1.

The percentage of fallen leaves was determined 6 days after application.

Components Application rate defoliation s in g / ha xn% (.n.Coloy) l-phenyl-3- (1,2,3- 2 »5 0 thiadiazol-5.-yl)“ ^ ^

urea '- I

K CO = II 500 0

^ J

K, Po0 „= III 500 0 4 2 7 I + II 2.5 + 500 14 (0) 10 + 500 46 (4) I + III 2.5 + 500 11 (0) 10 + 500 54 (4)

Example 7

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table.

Components application rate defoliation E

_ in g / ha_in% _ (n.Colby) 1-phenyl- (1,2,3-thiadiazol-5-yl) urea = I 40 19

KoC0 = II 3000 0 * -? L-.

m σι <o t "

-18- SCHERING AG

Intellectual Property

Components effort defoliation E

in g / ha in% (n.Colby) K4P2 ° 7 = 111 3000 ° I + II 40 + 300 57 (19) 40 + 1000 67 (19) 40 + 3000 71 (19) 40 + 10000 76 (19) I + III 40 + 1000 62 (19) • 40 + 3000 86 (19) 40 + 10000 90 (19)

Example 8

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table.

Components application rate defoliation E

__in g / ha_in% _ (n.Colby) 1-phenyl- (1,2,3- = I 40 33 thiadiazol-5-yl) - urea K2C0 ^ = II 540 0

Hexamethylene- = XVI 540 0 tetramine I + II 40 + 500 71 (33) Γ I + XVI 40 + 500 48 (33) -19- m 8

Board: Dr. Herbert Asm! S Dr. Christian BruhnHans-Jüraen Hamann Dn.t.n.HiriMβγηρβιμγ: in. n_inm n.riin «. «« M n

_19_ SCHERING AG

Intellectual Property

Example 9

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table.

Components application rate defoliation E

in g / ha in% (n.Colby) 1-phenyl- (1,2,3- 40 64

thiadiazol-5-yl) urea = I

k2co3 = II 500 0 k3po ^ = XVII 500 0 I + II 4o + 500 86 64 I + XVII 40 + 500 91 64

Example 10

Young cotton plants were treated as indicated in Example 1. The results are shown in the following table.

Components application rate defoliation E

in g / ha in% (n.Colby) 1-phenyl-l-methyl-40 63

(1,2,3-thiadiazol-5-yl) urea = XII

k2co3 = II 500 0 k3po4 = xvii 500 0 xii + ii 4o + 500 71 63 XII + XVII 40 + 500 76 63 -20-

A

m à T “4 Board: Dr. Herbert AsmisDr. Christian Bruhn. Hans-Jüroen Hamann Postal address: SCHERING AS. D-1000 Berlin SS - Postfach SS0311

_20- SCHERING AG

Intellectual Property

Example 11

Young cotton plants were treated as indicated in Example 1. The results are shown in the table below.

Components application rate defoliation E

in g / ha in% (n.Colby) 5-phenylcarbaraoyl- 40 52

imino) -1,2,3-thiadiazolin-2-id, magnesium salt = XIII

k3po ^ = XVII 500 0 XIII + XVII 40 + 500 71 52

Example 12

Young cotton plants were treated as indicated in Example 1. The results are shown in the table below.

Components application rate defoliation E

in g / ha in% (n.Colby) 5-phenylcarbamoyl-imino) -1,2,3-thiadiazolin-2-id, manganese salt = XIV 40 32 K ^ PO ^ = XVII 500 0 XIV + XVII> 40 + 500 82 32 «0 à« w T “A Board of Directors: Dr. Herbert AsmisDr. Christian Bruhn. Hans-Jureen Hamann Postal address: SCHERING AG »D-10ÛÛ Berlin 65> PO Box 650311

_81_ SCHERING AG

«Intellectual property law • i

Example 13

Young citrus plants with 21-27 leaves were treated as in Example 1. The results are shown in the table below.

Components application rate defoliation in g / ha in% 1-phenyl- (l, 2,3- 300 19

thiadiazol-5-yl) urea = I

K2C03 = II 1000 0 I + II 300 + 1000 48

Example 14

Young plants from Urtica urens were sprayed with the agent according to the invention or with the individual components. Three weeks later the fresh weight of the aerial parts of the plants was determined. The table below shows the relative values for plant height and fresh weight (untreated = 100). Compared to untreated controls, the plants had the desired stubborn, lower and therefore more stable growth. Nevertheless, her fresh weight was higher.

The results of the experiment show that the agent according to the invention produces a greater growth-regulating effect than the individual components.

/! -22-tn s f * 4 Board: Dr. Herbert AsmisDr. Christian BruhnHans-Jûrgen Hamann Postal address: SCHERING AG "D-1000 Berlin 65" PO Box 65 0311

_22. SCHERING AG

Intellectual Property

Components application s- plant height fresh concentration relatively weight in ppm relatively 1-phenyl- (1,2,3- 2 79 113 thiadiazol-5-yl) -

harastoff = I

κ2οο ^ = II 26 100 100 I + II 2 + 26 75 131/7 -23- m

S

4: Board: Dr. Herbert Asmis - Dr. Christian BruhnHans-Jürgen Hamann Postal address: SCHERING AG * D-1000 Berlin 65Postbox 650311

Claims (5)

1. PR a C, -C -AlkyIrest, a C "-C0-Cycloalkylrest, 2 15 P '··> a phenyl, halophenyl, C -C ^ alkylphenyl, C -C, -alkoxvnhenyl, nitrophenyl - or Trifluornethyl- lL ~ - s 7 i- 'phenylrest, an unsubstituted or a multiple identical or different by C ^ -C ^ -allcylreste, C ^ -C ^ -allcoxy, Ilalogenatone, the nitro group or the trifluoromethyl group substituted pyridyl or Pyrimidylrest or Λ m <h <nt / nratan ^ Π. U »kar4 Aamia. Π. ^ kri.iian D.nkn. U ^ n · luenan U ^ manit »i ^ LICQII> l / ^ 1Λ _ n_4 ^ ΛΛ fla.ll« ££ Ba.U. ff AA Λ Λ .2ll. SCHERING AG Intellectual Property Rights R and R0 together with the N atom represent the morpholino, piperidino or pyrrolidino group, R ^ hydrogen or a C ^ -C ^ alkyl radical and X is an oxygen or sulfur atom. 1. Agent, in particular for defoliation of plants, characterized by a content of a 1,2,3-thiadiazol-5-yl-urea or 1,2,3-thiadiazolin-2-id derivative in hybrid with a basic reacting substance . 2. Composition according to claim 1, characterized by a content of a 1,2,3-thiadiazol-5-yl-urea derivative of the general formula * -c - ax / ¾ Il II II / NC - N - C - NI in the R_ Hydrogen or a C -C_-All: yl radical, 3. Composition according to claims 1 and 2, characterized by a content of l-phenyl-3- (l, 2,3-thiadiazol-5-yl) urea, l-phenyl-l-methyl-3- (l12,3 -thiadiazol-5-yl) urea or 1- (2-pyridyl) -3- (l, 2,3-thiadiazol-5-yl) urea. 4. Composition according to claim 1, characterized by a content of a 1,2,3-tliiadiazolin-2-id derivative of the general formula H / N = C x RII II / 1 θ NC = N - C - NB II xxo in the R, hydrogen or a C, -CAlle », rlrest, 1. 1 D '*' R "hydrogen or a C-C_-Alkvlrest, a C_-Cn- 2 1 0" · -> Cycloal'kylrest, a phenyl, Ilalogenphenyl, C ^ -C alkylphenyl, C -C ^ - Alkoxyphenyl, nitrophenyl, or trifluoromethylplienyl, an unsubstituted or one or more identical or different by C ^ -C ^ alkyl, C ^ -C ^ alkoxy, halogen atoms, the nitro group or the Trif1uormetlvylgruppe substi- L · _25 ' n à «T * · Jz Board of Directors * ßr. Herbert A« mi <t. ßr Christian ftrnhn. Hana.Jifrnnn Hamann Pn ^ tanarbrÎft * SCHBRING AG · D-1000 Berlin 65 · POStfSCh 65 0311 „SCHERING AG mm 2 y ** Commercial legal protection «, the pyridyl or pyrimidyl radical or R and R together with the N atom mean the morpholino, piperidino or pyrrolidino group and B is an alkali metal atom, preferably a lithium, sodium or potassium atom, or a corresponding equivalent of one Zinc, manganese, calcium, magnesium or barium atoms, and X represent oxygen or sulfur. 5. Composition according to claims 1 and k, characterized by a content of 5- (phenylcarbamoylimino) -l, 2,3-thiadiazolin-2-id, calcium salt, 5-phenylcarbamoyl-imino) -1,2,3-thiadiazolin-2 -id, magnesium salt or 5-phenylcarbamoylimino) -1,2,3-thiadiazolin-2-id, manganese salt. 6. Composition according to claim 1, characterized by a content of a basic substance from the group of alkali metal hydroxides, amines, carbonates, phosphates or monocarboxylic acid Allcalisalze. 7. Composition according to claim 6, characterized by a content of sodium or halide hydroxide. 8. Composition according to claim 6, gekennzeichnex by a content zizi triethylamine, Dietiianolnnm (iriiit.mnoj-r.n. ’. N, ± rix so - propanolamine or hexamethylenetetramine. 9. Composition according to claim 6, characterized by a content of sodium carbonate, potassium carbonate or amnoniun carbonate. 10. Composition according to claim 6, characterized by a content of trisodium phosphate, trilcalium phosphate, tetra-? / z '' -26- 8 v. · Ft »UerkaH _ ft» ΛΚ »·« ιΙ «η (ünihn. Uanv ^ iïir ^ An Usmanfl PoitaniriifHt T SCHfRINâ A6 · D-1000 Berlin fiS. Postfsdl 65fi311 26. SCHERING AG * Commercial legal protection t »» sodium pyrophosphate or tetrapotassium pyrophosphate. 11. A composition according to claim 6, characterized by a content of sodium nolcat. 12. A composition according to claim 1, characterized by a content of l-phenyl-3- (1,2,3-thiadiazol-p-yl) urea in a mixture with potassium hydroxide, potassium carbonate, ammonium carbonate, tetrakali pyrophosphate, triethylamine, triethanolamine or Sodium oleate. 13 · Composition according to claim 1, characterized by a content of 1- (2-pyridyl) -3- (l, 2,3-thiadiazol-5-yl) urea in a mixture with potassium carbonate. 14. Composition according to claim 1, characterized by a content of 5-CFhenylcarbanoylimino) -1,2,3-thiadiazolin-2-id calcium salt in a mixture with potassium carbonate. 15. A composition according to claim 1, containing the individual components in a weight ratio of 1% by weight. I _ part of the defoliant substance to 0.5 to 1000 parts by weight of the basic substance. 16. Composition according to claim 1, characterized in that it has a pH greater than 8t, preferably from 9.5 to 11t5. 17. Composition according to claim 1, consisting of 5 to 95 weight percent Tîiiadiazol-5-yl-urea - or 1,2,3- / -27 "h m t o> m 4. J. n. U..U.U li η. ΛΙ. □ Pt »Kn. U.N·. Inrnan U «m1M Dnrl ^ ne ^ tirift · OP.UCOfWß Δβ. Π11 ΓίΤΠ Rprllfl · PflsHflfÎl fiS Û3 11 -27- SCHERINGAG Intellectual Property Law Tniadiazolin-i.-id-derj.vat mixed with a basic reacting substance, 95 tais 5% by weight of liquid or solid carriers and, if necessary, up to 30% by weight of surface-active substances. 1;. I lit tel genass claim 1 to the Eniblätt erunv of Dnnr.r.roll-Pflnnzen. ·. ΙλΛλΚλ ^ -23- V «05 Oi w * ·» 1 board; Dr. Herbert AsmîsDr. Christian Bruhn. Hans-.Ifirnan Hamann Pnstansrhrift * ift. O-tiWi Sartin «s. Dnetfarh ak iw