NZ198660A

NZ198660A - Synergistic preparations containing a 1,2,3-thiadiazol-5-yl-urea or a 1,2,3-thiadiazolin-2-ide with a basically reactive substance

Info

Publication number: NZ198660A
Application number: NZ198660A
Authority: NZ
Inventors: R Rusch; H R Kruger; E Richter
Original assignee: Schering Ag
Priority date: 1980-10-27
Filing date: 1981-10-15
Publication date: 1984-02-03
Also published as: RO84304B; FR2492632A1; HUT28333A; LU83705A1; CA1165580A; NL8104620A; TR21352A; IT1139268B; IL64096A; CH647928A5; GR74697B; JPS5799504A; BR8106908A; PH18494A; PL233556A1; FI65531C; CS221995B2; EG15216A; ZW25981A1; FI65531B

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number 1 98660 1986 Priority QaHs): .. ?V. JP. '.h CompSets Specification Fi!ed: (§.'!?$ P.O. Jczsnzsl No: .. . /A?ft r" t \ — NEW ZEALAND "C Patents Act 1953 COMPLETE SPECIFICATION "PREPARATIONS FOR DEFOLIATING AND/OR REGULATING THE GROWTH OF PLANTS AND THEIR USE." We, SCHERING AKTIENGESELLSCHAFT, a body corporate organized according to the laws of Germany, of 170-178 Mullerstrasse, D-1000 Berlin 65, Germany and Waldstrasse 14, 4619 Bergkamen, Germany, do hereby declare the invention, for which we pray that a Patent may be granted to us, and the method by which it is to be performed to be particularly described in and by the following statement 1 'i - 2 - ■j 98660 ro co C£ a. lu </■) O The present invention is concerned with, preparations for defoliating and/or regulating the growth of plants, especially for the defoliation of plants, preferably cotton plants, comprising a compoxind selected from 1,2,3-thiadia-5 zol-5-yl-urea derivatives and l,2,3-thiadiazolin-2-ide derivatives with a basically reactive substance, and with the use of such preparations. The term "plants" is understood herein to include trees and shrubs. 10 1,2,3-Thiadiazol-5-yl-urea derivatives and 1,2,3- thiadiazolin-2-ide derivatives have already become known as agents for the defoliation of plants These 15 active substances are not, however, sufficiently effective in all cases. Mixtures of 1,2,3-th.iadiazol-5-yl-urea derivatives with other defoliating agents are also already known in which the substances, which, per se, already have a more 20 or less strong defoliating action, are mutually potentiating in their action -The synergistic action of these mixtures is therefore dependent on two compounds that are already active. The aim upon which the present invention is based has therefore been to provide an agent especially for the defoliation of plants, in which the action of the 1,2,3-thiadiazol-5-yl-urea derivatives or 1,2,3-thiadiazolin-2-ide derivatives already known to be active is increased by n > LM O iu tr - 3 - .1986 6 0 the addition of substances' that are, per se. Inactive as regards a defoliating and/or growth regulating action. This aim is achieved by the present invention. The present invention accordingly provides a prepara-5 tion for defoliating and/or regulating the growth of plants, which comprises a defoliating and/or growth-regulating compound selected from l,2,3-thiadiazol-5-yl-urea derivatives and l,2,3-thiadiazolin-2-ide derivatives, in admixture or conjunction with a basically reactive substance. 10 The present invention also provides a method of de foliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture comprising (i) a defoliating and/or growth-regulating compound selected from l,2,3-thiadiazol-5-yl-urea derivatives and 15 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 20 comprising (i) a defoliating and/or growth-regulating compound selected from l,2,3-thiadiazol-5-yl-urea derivatives and l,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance. The preparations of the present invention may be in 25 the form of concentrates which on dilution provide mixtures suitable for the methods of the present invention. There is also included within the scope of the present - 4 - 1 98660 invention a pack which comprises a preparation of the present invention, together with instructions for its use for defoliating and/or regulating the growth of living plants. According to the present invention there come into consideration as the compounds having a defoliating and/or growth-regulating action: A) l,2,3-thiadiazol-5-yl-urea derivatives of the general formula I 10 C, - H X H_ I I (i) - N - C - H 3 I \ *3 2 in which represents a hydrogen atom or a C^-C^-alkyl group, represents a C^-C^-alkyl group, a C^-Cg-cycloalkyl group, a phenyl, halogenated phenyl, C^-C^-alkyl-15 phenyl, C^-C^-alkoxyphenyl, nitrophenyl or tri- fluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimldyl group substituted by one or more substituents (which may be the same or different) selected from C^-C^-alkyl groups, C^-C^-alkoxy groups, halogen atoms, nitre groups and trifluoromethyl groups, 20 - 5 - 1 98660 or R^ and fi2 together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, R^ represents a hydrogen atom or a C^-C^-alkyl group, and X represents an oxygen or sulphur atom; and B) l,2,3-thiadiazolin-2-ide derivatives of the general formula II © ! °l x ,c s H - C - H B® (II) S \ Xfi2 in which R^ represents a hydrogen atom or a C^-C^-alkyl group, ^2 represents a hydrogen atom, a C^-C^-alkyl group, a C^-Cg-cycl»alkyl group, a phenyl, halogenated phenyl, C^-C^-alkylphenyl, C^-C^-alkoxyphenyl, nitr•phenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituents (which may ber"the same or different) selected from alkyl groups, C^—C^-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or R^ and Rg together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, - 6 - 1986 6 0 * B represents an alkali metal atom, preferably a lithium, sodium or potassium atom, or a monovalent equivalent of zinc, manganese, calcium, magnesium or barium, and X represents an oxygen or sulphur atom. 5 As compounds of the general formula I there may be mentioned, for example, the compounds listed in the following Table 1. Table 1 l-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea 10 1-Phenyl-l-methyl-3-(1,2,3-thiadiazol-5-yl)-urea l-(4-Chlorophenyl)-3-(l,2,3-thiadiazol-5-yl)-urea 1-Cyclohexyl-3-(1,2,3-thiadiazol-5-yl)-urea l-(3-Chlorophenyl) -3- (l, 2,3-thiadiazol-5-yl) -urea l-(4-Methylphenyl)-3-(l ,2,3-th.iadiazol-5-yl) -urea 15 1-(3-Methylphenyl)-3-(1,2,3-thiadiazol-5-yl)-urea l-(3,4-Dichlorophenyl)-3-( 1,2,3-thiadiazol-5 -yl) -urea 1-Methyl-3- (1,2,3-thiadiazol-5-yl)-urea 1, l-Dimethyl-3-(l, 2,3-thiadiazol-5-yl) -urea 1,1-Dimethy1-3-me thyl-3-(1,2,3-thiadiazol-5-yl)-urea 20 1-Methy 1-3-me thyl-3- (1,2,3-thiadiazol-5-yl) -urea l-Phenyl-3-( 1,2»3-thiadiazol-5-yl)-thiourea 1- (4-Chlor ophenyl) -3- (1,2,3-thiadiazol-5-yl) -thiourea 1-(2-I^yridyl)-3-(1,2,3-thiadiazol-5-yl)-urea l-(5-Chloro-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea 25 1- (4-Me thyl-2-pyridyl) -3- (1,2,3-thiadiazol-5-yl) -urea 1- (4-Methyl-2-pyrimidyl )-3-(l,2,3-thiadiaz ol-5-yl) -urea - 7 - .1986 l-( 4-Pyridyl )-3- (l» 2,3-thiadiazol-5-yl)-urea l-(3-Pyridyl)-3-(1,2,3-thiadiazol-5-yl) r-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 5 l-(5-Methyl-2-pyridyl)-3-(l,2,3-thiadiazol-5-yl)-urea l-(6-Methyl-2-pyridyl)-3-(l,2,3-thiadiazol-5-yl)-urea. As compounds of the general formula II there may be mentioned, for example, the compounds listed in the following Table 2. 10 Table 2 5- (Phenylcarbamoylimino) -1,2,3-thiadiazolin-2-ide, sodium salt acHgO 5- (Phenylcarbamoylimino )-l, 2,3-thiadiazolin-2-ide, calcium salt xEiHgO 15 5-(Phenylcarbamoylimino) -1,2, 3-thiadiazolin-2-ide, potassium salt xHgO 5-(Phenylcarbamoyl3mino)-l,2,3-thiadiazol1n-2-ide, lithium salt x4H^0 5- (Methylphenylcarbamoylimino ) -1,2,3-thiadiazolin-2-ide, 20 sodium salt xB^O 5- (Methylphenylcarbamoylimino ) -1,2,3-thiadiazolin-2-ide, potassium salt xH^O 5-(Methylphenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, lithium salt xH^O 25 5-(2-Pyridylcarbamoylimi no)-1,2,3-thiadiazolin-2-ide, sodium salt xl.5 HgO 5-(2-Pyridylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, potassium salt xHgO 5- (2-Pyridylcarbamoylimino ) -1,2,3-thiadiazolin-2-ide, 30 lithium salt xHgO 5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, eodium salt ±H20 198660 - 8 - 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, magnesium salt xZQ^O 5-(Phenylcarbamoylimino)-l,2,3-thiadiazolin-2-ide, zinc salt xJHgO 5 5- (Phenylcarbamoylimino )-1,2,3-thiadiazolin-2-ide f manganese salt x3H20 5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, barium salt Of these compounds, the following are especially 10 suitable for the preparations and methods of the present invention: l-phenyl-3-(1,2,3-thiadiaz o1-5-yl)-urea, l-phenyl-l-methyl-3-(l,2,3-thiadiazol-5-yl)-urea, 1- (2-pyridyl) -3-(1,2,3-thiadiazol-5-yl)-urea and 15 5-(phenylcarbamoylimino)-l,2,3-thiadiazolin-2-ide salts, for example the calcium, magnesium and manganese salts. The following may be mentioned as substances not, on their own, having any defoliating and/or growth-regulating activity, but being suitable as the basically reactive eub-20 stances for the preparations and methods of the present invention: -..y metal alkali! hydroxides. for example sodium and potassium hydroxides, amines, for example alkylamines, for example triethylamine, alkanolamines, for example diethanolamine, triethanolamine 25 and triisopropanolamine, and hexamethylenetetramine, carbonates. for example sodium carbonate, potassium carbonate and ammonium carbonate, 37 phosphates, for example tertiary phosphates, for example o trisodium phosphate and tripotassium phosphate, and pyro- Sim ij z K) N O -o > l/> m n? "o vO OO 1 986 60 - 9 - phosphates, for example tetrasodium pyrophosphate and tetrapotassium pyrophosphate, alkali saltB of monocarboxvlic acids, for example sodium oleate. 5 It is preferable to use basically reactive substances that adjust the preparations of the present invention and the mixtures used in the methods of the present invention to a pH-value of more than 8, preferably within the range of from 9«5 to 11.5* 10 Surprisingly, the mixtures of the defoliating and/or growth-regulating compounds and the basically reactive substances when used according to the present invention have an action that is greater than that of the individual components. They are therefore especially suitable for 15 the defoliation of cotton plants whereby, in an ideal manner, the use of picking ma,chines for boll harvesting is rendered possible. Other plants can, however, also be advantageously defoliated and/or influenced in their growth, as examples 20 of which there may be mentioned the promotion of bushiness, formation of side-shoots, and inhibition of root growth in the case of grasses and dicotyledons, for example hibiscus, apple trees and other woody plants. Therefore the preparations according to the present invention can be used advan-25 tageously both for defoliating plants and also for regulating their growth. It is known to the man skilled in the art that 1986 6 - 10 - defoliation is not a herbicidal action and that it is not desired actually to kill the treated plants because the leaves still remain attached to "the dead plants and the productive parts of the plant can be damaged. The aim of 5 defoliation, that is to facilitate harvesting and to obtain a purer harvested crop, can be lost as a result of this. It is therefore necessary for the plants to remain alive while the leaves are becoming detached and falling off. This permits the further development of the productive parts 10 of the plant while the re-growth of new leaves is prevented. The mixtures used in accordance with the present invention achieve all these aims in an advantageous manner so that it can be assumed that the prior art is far exceeded. The mixture of the defoliating and/or growth-regulating 15 compound and the basically reactive substance in accordance with the present invention can also be used in admixture with other active substances, for example defoliating agents, plant-protecting agents and/or pesticides, depending on the desired purpose. Thus, the preparations of the present 20 invention may contain such further active substances. The action and the speed of action can also be promoted, for example by action-increasing additives, for example organic solvents, wetting agents and oils. This permits a further decrease in the quantity of the actual active 25 substances used. The mixture of the defoliating and/or growth-regulat-ing compound and the basically reactive substance in J 98660 - 11 - accordance with the present invention is advantageously used in the form of preparations, for example powders, strewable preparations, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or 5 diluents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing agents. Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarhons, for example benzene, 10 toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethylformamide, and also mineral oil fractions. Suitable solid carriers are, for example, mineral earths, for example tonsil, silica gel, talcum, kaolin, 15 attaclay, limestone and silicic acid, and vegetable products, for example meals. As surface-active agents there may be mentioned, for example, sodium or calcium lignin sulphonate, polyoxyethy-lene^aLkylphenyl ethers, naphthalenesulphonic acids and 20 salts thereof, phenolsulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates, salts of long-chained fatty acids and also substituted benzene-sulphonic acids and salts thereof. The proportion of the essential constituents, namely 25 the defoliating and/or growth-regulating compound and the basically reactive substance, in the various preparations may vary within wide limits. For example, the preparations - 12 .1986 of the present invention and the mixtures used in the methods of the present invention may contain approximately from 5 to 95$ by weight of these constituents, approximately from 95 to 5i° by weight of liquid and/or solid carrier(s) 5 and also, if desired, up to 30$ by weight of surface-active agent(s). The relative ratio by weight of the essential constituents in the various preparations is advantageously approximately 1 part by weight of the compound having a 10 defoliating and/or growth-regulating action to 0.5 to 1000 parts by weight of the basically reactive substance, and depends on the sensitivity and resistance of the plants, the time of application, the climatic conditions and the soil conditions. 15 The quantities applied of the mixture of the defoliat ing and/or growth-regulating compound and the basically reactive substance for the desired defoliation and/or growth-regulating action are generally within the range of from 1 to 10,000 g per hectare, preferably from 10 to 1000 g 20 per hectare. The mixture of the defoliating and/or growth-regulat-ing compound and the basically reactive substance may be applied in the conventional manner, for example with water as the carrier, in quantities of spray liquor of approxi-25 mately from 100 to 1000 litres/hectare. It is also possible to apply these mixtures by the so-called "low-volume M or "ttltra-low-volumeM method. The compounds having a defoliating and/or growth- # J 986 6 0 - 13 - regulating action and the basic additives contained in the preparations of the present invention and in the mixtures used in the methods of the present invention are known per se and may be manufactured according to methods known 5 per se. For the manufacture of the preparations of the present invention, there may be used, for example, the constituents listed under a), b), c) or d) in the following Table 3, the mixture in each case of course referring to the mixture of 10 the defoliating and/or growth-regulating compound and the 15 20 25 basically reactive substance# Table 3 a) 95 # by weight of mixture 4 % by weight of kaolin 1 * by weight of surface-active agents baseion the sodium salt of H-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 * *y weight of cellulose pitch 2 % by weight of wetting agent based on a fatty acid 10 J 986 6 0 - 14 - condensation product d) 5 i» by weight of mixture 80 $ by weight of tonsil 10 # by weight of cellulose pitch 5 i° by weight of wetting agent based on a fatty acid condensation product The preparations of the present invention are manufactured, for example, by mixing the individual constituents in a drum and then grinding in a mill. These preparations may be applied either directly or after dilution with water to the plants to be treated. The pH-value of these preparations is of special importance for potentiating the action of the essential components and should advantageously be greater than 8, preferably within 15 the range of from 9.5 to 11.5. It thus represents a special embodiment of the present invention. The following Examples illustrate the invention. iDhe Examples are based on greenhouse tests that were generally carried out on cotton plants having from 5 to 8 true foliage 20 leaves. The mixtures of the defoliating and/or growth-regulating compound and the basically reactive substance were applied in the form of aqueous preparations based on the compositions described above. The tests in Examples 1 to 13 were evaluated by count-25 ing the number of leaves shed after the application and by calculating the proportion as a percentage of the total number of leaves. In the individual tests, the same number 198660 - 1? — of leaves was always available per test member. The number of leaves per test member varied from test to test between 20 and 28 foliage leaves per test member. The following Examples 1 to 13 contain information on 5 the active substance, basically reactive substance, mixture, quantity applied, and the percentage defoliation determined. In some cases there is indicated in brackets after the percentage defoliation obtained by the combinations, the value calculated according to the method described by S.R. Colby 10 which would be expected in the case of an additive action [S.R. Colby "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations" Weeds 15/l (1967) p. 20-22]. This calculation was made according -to the following 15 equation: E = X + T - 21 100 in which X = percentage defoliation with substance A using p kg of active substance/ha T = percentage defoliation with substance B using 20 ^ kg of active substance/ha E = expected defoliation by A + B using P + £ kg/ha If the value observed is greater than the value E calculated according to Colby then the combination has a synergistic action. The results of Examples 1 to 13 clearly 25 show the potentiation of action of the substance having a defoliating action by the basically reactive substances that are themselves inactive as defoliants. - 16 - J 9 86 V Example 1 Young cotton plants at the stage of having 5 foliage leaves were treated in a series of tests with the mixtures indicated in the Table below and with the individual components of the mixtures, namely the active substance and the basically reactive substance (repeated 4 times). The quantity of water used as carrier was 500 litres/ha. After a few days the percentage of shed leaves was determined. The results are given in the following Table: 10 Components Application quantity in g / ha Defoliation as a ^ E (according to Colby) l-phenyl-3-(1,2.3-thiadiazol-5-yl)-15 urea = I K2co5 K4P2°7 = ii = hi i + ii 80 500 500 80 + 500 i + iii 80 + 500 35 0 0 70 60 (35) (35) 20 Example 2 Young cotton plants were treated as indicated in Example 1. The results are given in the following Table. Components 25 Application quantity in g / ha Defoliation as a^ E (according to Colby) l-phenyl-3-(1>2.3-thiadiazol-5-yl)-urea = I 80 57 K2co3 = ii 500 - 17 - J 98660 Components Application quantity in g / ha Defoliation as a $ (according to Colby) HagCOj (»H4)2OO3 KOH 10 XV 500 0 IV 500 0 V 500 0 I + II 80 + 500 70 I + XV 80 + 500 85 I + IV 80 + 500 80 I + V 80 + 500 60 (57) (57) (57) (57) 15 Exam-pie 3 Young cotton plants were treated as indicated in Example 1. The results are given in the following Table. Components Application quantity in g / ha Defoliation as a (according to Colby) l-phenyl-3-(1,2.3-thiadiazol-5-yl5- = I 40 urea 20 Ua-oleate = VI 500 triethanolamine = VII 500 triethylamine = VIII 500 I + 71 40 + 500 I + VII 40 + 500 25 I + VIII 40 + 500 29 0 0 O 33 43 62 (29) (29) (29) •RTRinpl^ 4 Young cotton plants were treated as indicated in .1986 6 0 - 18 - Example 1. The lower percentage action compared with the above Examples can be attributed ta unfavourable environmental conditions when the tests were carried out in the winter months. The results are given in the 5 following Table. Components Application Defoliation quantity as a ^ in g / ha l-phenyl-3-(1,2.3- 80 0 10 thiadiazol-5-yl)-urea = I K~C0, =11 500 0 * * 1,000 0 I + II 80 + 500 29 5-(phenyl- 80 0 15 carbamoylimino)-1.2,3- thiadiazolin-2-ide, calcium salt = IX 20 IX + II 80+500 24 l-(2-pyridyl)- 80 0 3-(l,2,3- x thiadiazol-5-yl)-urea = X 25 X + II 80 + 500 23.5 Example 5 Young cotton plants were treated as indicated in Example 4. The results^are given in the following Table. - 19 - 198660 Components Application quantity in g / ha Defoliation E as a (accordir^g to Colby) 5-(phenylcarbamoyl-imino)-1,2,3-thiadiazolin-2-ide, potassium salt = XI K2c°3 500 = II 500 XI + II 500 + 500 17 0 39 (17) 10 Example 6 Young hibiscus plants each having from 7 to 10 unfolded leaves were treated as indicated in Exeimple 1, The percentage of shed leaves was determined 6 days after the treatment. 15 Components Application quantity in g / ha Defoliation as a (according to Colby) l-phenyl-3- (1,2.3-thiadiazol-5-ylv-20 urea 25 z2co3 K4P2°7 = I = II = III 2.5 10 500 500 I + II 2.5 + 500 10 + 500 I + III 2.5 + 500 10 + 500 0 4 14 46 11 54 (0) (4) (0) (4) Example 7 Young cotton plants were treated as indicated in 198660 - 20 - Example 1. The results are given in the following Table. Components Application Defoliation E quantity as a $ (according in g / ha to Colby) l-phenyl-3-(1,2,3-thiadiazol-5-yl)- urea sb I 40 19 K2C03 = II 3000 0 10 V2°7 = III 3000 0 I + II 40 + 300 57 (19) 40 + 1000 67 (19) 40 + 3000 71 (19) 40+10000 76 (19) 15 I + III 40 + 1000 62 (19) 40 + 3000 86 (19) 40 +10000 90 (19) Example 8 Young cotton plants were treated as indicated in 20 Example 1. The results are given in the following Table. Components Application quantity in g / ha Defoliation E as a ^ (according to Colby) l-phenyl-3-25 (1,2,3- thiadiazol-5-yl)-= I urea X2 C0? = II 40 540 33 - 21 - 198660 Components Application v Defoliation E quantity as a $ (according in g / ha . to Colby) hexamethylene- 5 tetramine = XVI 540 tI + II 40 + 500 I + XVI 40 + 500 0 71 48 (33) (33) Example 9 Young cotton plants were treated as indicated in 10 Example 1. The results are given in the following Table. Components Application quantity in g / ha Defoliation E as a (according to Colby) l-phenyl-3-15 (1,2,3- thiadiazol-5-yl)-= I urea Tt2C03 V°4 20 40 = II = XVII I + II I + XVII 500 500 40 + 500 40 + 500 64 0 0 86 91 (64) (64) Example 10 Young cotton plants were treated as indicated in Example 1. The results are given in the'following Table* - 22 - 1198660 Components Application Defoliation E quantity as a (according in g / ha to Colby) , 1-phenyl-l-methyl- 40 63 5 3-vl.2,3-thiadiazol- 5-yl)-urea = XII Z2C05 = II 500 0 K3P04 = XVII 500 0 XII + II 40+500 71 (63) 10 XII + XVII 40 + 500 76 (63) Example 11 Young cotton plants were treated as indicated in Example 1. The results are given in the following Table< Components Application Defoliation E 15 quantity as a ^ (according in g / ha to Colby) 5-(phenylcarbamoyl- 40 52 imino)-1,2,3-thiadiazolin-2-ide» 20 magnesium salt = XIII K5P04 = XVII 500 0 XIII + XVII 40 + 500 71 (52) Example 12 Young cotton plants were treated as indicated in 25 Example 1. The results are given in the following Table* - 23 - 198660 Components Application Defoliation E quantity as a $ (according in g / ha . to Colby 5- (phenyl carbamoyl-imino)-1,2,3-thiadiazolin-2-ide, manganese salt = XIV 40 V°4 32 = XVII 500 0 XIV + XVII 40 + 500 82 (32) 10 Example 13 Young cotton plants having from 21 to 27 leaves were treated as indicated in Example 1. The results are given in the following Table. 15 Components Application quantity in g / ha -Defoliation as a $ l-phenyl-3- (1,2.3-thiadiazol- 5-yl)-urea = I 20 K2co5 = II I + II 300 1000 300 + 1000 19 0 48 Example 14 In a series of tests young Urtica urens plants were sprayed with the mixture according to the present invention 25 indicated in the Table below and with the individual components of the mixture. Three weeks later the fresh weight of the parte of the plants above the soil was determined. The following Table gives the relative values for plant </div>

Claims

<div class="application article clearfix printTableText" id="claims">



1 98660 

- 24 - 

height and the fresh weight (untreated = 100). As compared with the untreated control plants» the treated plants had the desired more compact, lower and therefore more stable 

» . 

growth. Their fresh weight was nevertheless greater. The results of the tests show that the mixture according to the present invention brings about a greater growth-regu-lating action than the individual components. 

Components Application Relative Relative concentration plant fresh in ppm height weight l-phenyl-3- 2 79 113 

(1.2,3- 

thiadiazol-5-yl)-urea = I 

Z2C03 = II 26 100 100 

I + II 2 + 26 75 131 

- 25 - 

198660 

WHAT VTE CLAIM IS: 

r_ synergistic preparation for 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 derivatives and 1,2,3-thiadiazolin-2-ide derivatives, in admixture or conjunction with a basically reactive substance.
2. A preparation as claimed in claim 1, wherein the defoliating and/or growth-regulating compound is a 1,2,3-thiadiazol-5-yl-urea derivative of the general formula I 

I 

N 

C — H 

X 

II 

-N - C - N I • 

*3 

R, 

(I) 

5 in which ea e* 

O 

R] 

R, 

10 

represents a hydrogen atom or a C^-C^-alkyl group, represents a C^-C^-alkyl group, a 05-08 -cycloalkyl group, a phenyl, halogenated phenyl, C^-C^-alkylphenyl, C^-C^-alkoxyphenyl, nitrophenyl or trifluoromethyl-phenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituente selected from C^-C^-alkyl groups, C^-C^-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, 

- 26 - 

1 9 86 6 0 

15 or R^ and Eg together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, 

represents a hydrogen atom or a C^-C^-alkyl group, and 

20 X represents an oxygen or sulphur atom.
3. A preparation as claimed in claim 2, wherein the l,2,3-thiadiazol-5-yl-urea derivative is any one of the compounds listed in Table 1 herein.
4. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is l-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea.
5. A preparation as claimed in claim 2, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-phenyl-l-methyl-3-(1»2,3-thiadiazol-5-yl)-urea.
6. A preparation as claimed in claim 2, wherein the l,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 defoliating and/or growth-regulating compound is a 1,2,3-thiadiazolin-2-ide derivative of the general formula II 

/R1 

c = n - c - ij b © (ii) 

© 

*2 

5 in which 

J 98660 

- 27 - 

represents a hydrogen atom or a C^-C^-alkyl group, Rg represents a hydrogen atom, a C^-C^-alkyl group, a C5-Cg—cycloalkyl group, a phenyl, halogenated phenyl, C^-C^-alkylphenyl, C^-C^-alkoxyphenyl, nitro-phenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituents selected from C^-C^-alkyl groups, C^-C^-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or 

R^ and R^ 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 2 represents an oxygen or sulphur atom.
8. A preparation as claimed in claim 7, wherein B represents a lithium, sodium or potassium atom.
9. A preparation as claimed in claim 7* wherein the l,2,3-thiadiazolin-2-ide~derivative is any one of the compounds listed in Table 2 herein.
10. A preparation as claimed in claim 7, wherein the l,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 l,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimi.no)-l,2,3-thiadiazolin-2-ide.
12. A preparation as claimed in claim 7» wherein the 

- 28 - 

•; OO / f i 

I ^ u C O L 

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 any oneixif claims 1 

to 12, wherein,the basically reactive substance is an metal alkali) hydroxide, an amine, a carbonate, a phosphate or r metal an alkali|salt of a monocarboxylic acid.
14. A preparation as claimed in claim 13» wherein the i- metal alkali Jhydroxide is sodium or potassium hydroxide.
15. A preparation as claimed in claim 13, wherein the amine is triethylamine, diethanolamine, triethanolamine, triisopropanolamine or hexamethylenetetramine.
16. A preparation as claimed in claim 13, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
17. A preparation as claimed in claim 13, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
18. A preparation as claimed in claim 13, wherein the metal alkali[salt of a monocarboxylic acid is sodium oleate.
19. A preparation as claimed in claim 1, which comprises l-phenyl-3-(l,2,3-thiadiazol-5-yl)r?urea as the defoliating and/or growth-regulating compound in admixture with potassium hydroxide, potassium carbonate, ammonium carbonate, 

5 tetrapotassium pyrophosphate, triethylamine, triethanolamine or sodium oleate as the basically reactive substance.
20. A preparation as claimed in claim 1, which comprises l-(2-pyridyl)-3-(l»2,3-thiadiazol-5-yl)-ure& the 

N.Z. PATENT OFFICE 

26SEP1983 

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198660 

defoliating and/or growth-regulating compound in admixture with potassium carbonate as the basically reactive substance.
21. A preparation as claimed in claim 1, which comprises the calcium salt of 5-(phenylcarbamoylimino)-l,2,3-thia-diazolin-2-ide as the defoliating and/or growth-regulating compound in admixture with potassium carbonate as the basically reactive substance.
22. A preparation as claimed in any one of claims 1 to 

21, wherein the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance is within the range of from 1:0.5 to 1:1000.
23. A preparation as claimed in any one of claims 1 to 

22, having a pH-value greater than 8.
24. A preparation as claimed in claim 23, having a pH-value within the range of from 9.5 to 11.5.
25. A preparation as claimed in any one of claims 1 

to 24, which also contains a liquid carrier and/or a solid carrier.
26. A preparation as claimed in claim 25, containing 

5 to 95# by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5# by weight of the liquid and/or solid carrier(s).
27. A preparation as claimed in any one of claims 1 to 26, which also contains a surface-active agent,
28. A preparation as claimed in claim 27, containing the surface-active agent in an amount of up to 30$ by weight.
29. A preparation as claimed in any one of claims 1 to 28, 

- 30 - 

1 98660 

which also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than l,2,3-thiadiazol-5-yl-urea deriva-5 tives and l,2,3-thiadiazolin-2-ide derivatives.
30. A preparation as claimed in any one of claims 1 to 29, which is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
31. Any one of the preparations substantially as described in Table 3 herein.
32. Any one of the preparations as claimed in claim 1 and substantially as described in Examples 1 to 14 herein.
33• A pack which comprises a preparation as claimed in any one of claims 1 to 32, together with instructions for its use for defoliating and/or regulating the growth of living plants.
34. A method of defoliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture comprising (i) a defoliating and/or growth-regulating compound selected from l,2,3-thiadiazol-5-yl- 

5 urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
35. A method as claimed in claim 34, wherein the defoliating and/or growth-regulating compound is a 1,2,3-thiadiazol-5-yl-urea derivative of the general formula I given in claim 2, in which R^, Rg, R^ and X have the mean- 

5 ings given in claim 2.
36. A method as claimed in claim 35, wherein the 1,2,3- 

- 31 - 

1 98660 

thiadiazol-5-yl-urea derivative is any one of the compounds listed in Table 1 herein.
37* A method as claimed in claim 35, vherein the 1,2,3-thiadiazol-5-yl-urea derivative is l-phenyl-3-(l,2,3-thiadiazol-5-yl)-urea.
38. A method as claimed in claim 35, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is l-phenyl-l-methyl-3-(1,2,3-thiadiazol-5-yl )-urea.
39» A method as claimed in claim 35, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is l-(2-pyridyl)-3-(l,2,3-thiadiazol-5-yl)-urea•
40. A method as claimed in claim 34, wherein the defoliating and/or growth-regulating compound is a 1,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which E^, ® and X have the meanings given in claim 7.
41* A method as claimed in claim 40, wherein B represents a lithium, sodium or potassium atom.
42. A method as claimed in claim 40, wherein the 1,2,3-thiadiazolin-2-ide derivative is any one of the compounds listed in Table 2 herein.
43. A method as claimed in claim 40, wherein the 1,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5- 

(phenylcarbamoylimino )-l, 2,3-thiadiazolin-2-ide.
44. A method as claimed in claim 40, wherein the 1,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5- 

(phenylcarbamoylimino )-l, 2,3-thiadiazolin-2-ide. 

- 32 - 

i 9 8660
45• A method as claimed in claim 40, wherein the 1,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5- (phenylcarbamoylimino ) -1,2,3-thiadiazol±n=-2-ide.
46. A method as claimed in any one of claims 34- to 45, 

wherein the basically reactive substance is an alkali metal hydroxide, an amine, a carbonate, a phosphate or an alkali metal salt of a monocarboxylic acid.
47. A method as claimed in claim 46, wherein the alkali metal hydroxide is sodium or potassium hydroxide.
48. A method as claimed in claim 46, wherein the amine is triethylamine, diethanolamine, triethanolamine, triiso-propanolamine or hexamethylenetetramine.
49• A method as claimed in claim 46, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
50. A method as claimed in claim 46, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
51. A method as claimed in claim 46, wherein the alkali metal salt of a monocarboxylic acid is sodium oleate.
52. A method as claimed ±n claim 34, wherein the mixture is a mixture comprising l-phenyl-3-(l,2,3-thiadiazol-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, 

5 triethanolamine or sodium oleate*
53 • A method as claimed in claim 34, wherein the mixture is a mixture comprising l-(2-pyridyl)-3-(l»2,3-thiadiazol-5- 

N.Z. PATENT OFFICE 

26SEP1983 

1 9 86 6 0 

- 33 - 

yl)-urea and potassium carbonate. ~
54. A method as claimed in claim 34,. wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarba-moyliBiino)-lt2f3-thiadiazolin-2-ide and potassium carbonate.
55. A method as claimed in any one of claims 34 to 54, 

wherein the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive sub-.. 

stance in the mixture is within the range of from 1:0.5 to 

5 1:1000.
56. A method as claimed in any one of claims 34 to 55, 

wherein the pH-value of the mixture is greater than 8.
57. A method as claimed in claim 56, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
58. A method as claimed in any one of claims 34 to 57, 

wherein the mixture also contains a liquid carrier and/or a solid carrier.
59. A method as claimed in claim 58, wherein the mixture contains 5 to 95^ by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5$ by weight of the liquid and/or solid 

5 carrier(s).
60. A method as claimed in any one of claims 34 to 59, 

wherein the mixture also contains a surface-active agent.
61. A method as claimed in claim 60, wherein the mixture contains up to 30$ by weight of the surface-active agent.
62. A method as claimed in any one of claims 34 to 61, 

- 34 - 

1 986 

wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than l,2,3-thiadiazol-5-yl-5 urea derivatives and l,2,3-thiadiazolin-2-ide derivatives,
63. A method as claimed in any one of claims 34 to 62, wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension,
64. A method as claimed in claim 34, wherein the mixture is any one of the preparations substantially as described in Table 3 herein,
65. A method as claimed in claim 34, conducted substantially as described herein.
66. A method as claimed in claim 34, conducted substantially as described in Example 14 herein.
67. 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 compound selected from 1,2,3-thiadiazol- 

5 5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
68. A method as claimed in claim 67, wherein the defoliating and/or growth-regulating compound is a 1,2,3-thiadiazol-5-yl—urea derivative of the general formula I given in claim 2, in which E^, E^ and X have the meanings given 

5 in claim 2,
69. A method as claimed in claim 68, wherein the 1,2,3-thiadiazol-5-yl-u^ea derivative is any one of the compounds listed in Table 1 herein. 

198660 

- 35 -
70. A method as claimed in claim 68, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-pheny 1-3-(1,2,3-thiadiazol-5-yl)-urea.
71. A method as claimed in claim 68, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is l-phenyl-l-methyl-3- 

(1,2,3-thiadiazol-5-yl)-urea.
72. A method as claimed in claim 68, wherein the 1,2,3-thiadiazol-5-yl-urea derivative is 1-(2-pyridyl)-3-(1,2,3-thiad iaz o1-5-yl)-urea.
73. A method as claimed in claim 67, wherein the defoliating and/or growth-regulating compound is a 1,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which H^, ® an<* ^ have the meanings 

5 given in claim 7.
74. A method as claimed in claim 73, wherein B represents a lithium, sodium or potassium atom.
75. A method as claimed in claim 73, wherein the 1,2,3-thiadiazolin-2-ide derivative is any one of the compounds listed in Table 2 herein.
76. A method as claimed in claim 73, wherein the 1,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5- * 

(phenylcarbamoylimino)—1,2,3-thiadiazolin-2-ide.
77. A method as claimed in claim 73, wherein the 1,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 

5-(phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide.
78. A method as claimed in claim 73, wherein the 1,2,3-thiadiazolin-2-ide derivative is the manganese salt of 

\98660 

- 36 - 

5-(phenylcarbamoylimino)-l, 2 ,3-thiadiazolin-2-ide.
79. A method as claimed in any one of claims 67 to 78, 

wherein the basically reactive substance ife-an alkali metal hydroxide, an amine, a carbonate, a phosphate or an 

- metal aliali|salt of a monocarboxylic acid.
80. A method as claimed in claim 79, wherein the alkali metal hydroxide is sodium or potassium hydroxide.
81. A method as claimed in claim 79, wherein the amine is triethylamine, dietbanolamine, triethanolamine, tri-isopropanolamine or hexamethylenetetramine.
82. A method as claimed in claim 79, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
83. A method as claimed in claim 79, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetra-sodium pyrophosphate or tetrapotassium pyrophosphate.
84. A method as claimed in claim 79, wherein the 

9 

alkali salt of a monocarboxylic acid is sodium oleate.
85. A method as claimed in claim 67, wherein the mixture is a mixture comprising l-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, triethanolamine or sodium oleate.
86. A method as claimed in claim 67, wherein the mixture is a mixture comprising l-(2-pyridyl)-3-(l,2,3-thiadiazol-5-yl)-urea and potassium carbonate.
87. A method as claimed in claim 67, wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarba- 

19 86 

- 37 - 

moylimino)-l,2,3-thiadiazolin-2-ide and potassium carbonate.
88. A method as claimed in any one of claims 67 to 87, wherein the ratio by weight of the defoliating and /or growth-regulating compound to the basically reactive substance in the mixture is within the range of from 1:0.5 

5 to 1:1000.
89. A method as claimed in any one of claims 67 to 88, wherein the pH-value of the mixture is greater than 8.
90. A method as claimed in claim 89, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
91. A method as claimed in amy one of claims 67 to 90, wherein the mixture also contains a liquid carrier and/or a solid carrier.
92. A method as claimed in claim 91, wherein the mixture contains 5 to 95$ by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5$ by weight of the liquid and/or solid carrier(s).
93. A method as claimed in any one of claims 67 to 92, wherein the mixture also contains a surface-active agent.
94. A method as claimed in claim 93, wherein the mixture contains up to 30$ by weight of the surface-active agent.
95. A method as claimed in any one of claims 67 to 94, wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than lf2,3-thiadiazol-5-yl-urea 

5 derivatives and, 1,2,3-thiadiazolin-2-ide derivatives.
96. A method as claimed in any one of claims 67 to 95, 

-.38 - 

198660 

wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
97. A method as claimed in claim 67, wherein the mixture is any one of the preparations substantially as described in Table 3 herein.
98. A method as claimed in any one of claims 67 to 97, wherein the total amount of the defoliating and/or growth-regulating compound and the basically reactive substance used for the treatment is within the range of from 1 to 10,000 grams per hectare.
99. A method as claimed in claim 98, wherein the total amount is within the range of from 10 to 1000 grams per hectare.
100. A method as claimed in any one of claims 87 to 99, wherein the crop area contains cotton plants,
101. A method as claimed in claim 67, conducted substan- 

v tially as described herein,
102. A method as claimed in claim 67, conducted substantially as described in any one of Examples 1 to 13 herein. 

M^TEMTOFBCB 

15 OCT 1981 { 

.SCHEfii MG AKT1 £NG.E SELLSCHAFI 

By Wte/Their Attorneys, HENRY JHI^HES^IJJMJTED, Per ^ 



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