CH563711A5 - Agents for regulating plant metabolism - contg. imidazolidine-2,4,5-trione-3-carboxylic acid derivs. - Google Patents

Abstract

Agents for regulating plant metabolism contain >=1 imidazolidinetrione-carboxylic acid deriv. of formula (I) or an acid-addn. salt thereof. (where R1 is H, alkyl, alkenyl, a cycloaliphatic gp. alkoxycarbonyl, alkylthiocarbonyl, an alkyl gp. substd. by cycloalkyl, alkoxy, alkoxycarbonyl, alkoxy-alkoxycarbonyl, alkylthio, dialkylamino or halogen, an alkenyloxyalkyl gp. a phenyl gp. opt. substd. by halogen, NO2, lower alkyl, alkoxy, haloalkyl or CN, tetrahydro-3-thienyl S,S-dioxide, a benzyl or phenethyl gp. opt. ring-substd. by halogen, NO2 and/or lower alkyl, or tetrahydrofurfuryl; R2 is alkyl, alkenyl, alkynyl, a cycloaliphatic gp. an alkyl gp. substd. by cycloalkyl, alkoxyalkoxycarbonyl, alkenyloxy, alkoxy or halogen a phenyl gp. opt. substd. by halogen, NO2, lower alkyl, haloalkyl or CN, a benzyl or phenethyl gp. opt. ring-substd. by halogen, NO2 and/or lower alkyl, or a furfuryl or tetrahydrofurfuryl gp; Y is O or S). Cpds. (I) are esp. useful for promoting fruit abscission (e.g. for facilitating the mechanical harvesting of citrus fruits, apples, pears, stone fruits and olives) and for inhibiting senescence (e.g. for extending the life of cut flowers).

Description

  

  
 



   The present invention relates to an agent for regulating plant metabolism which contains new imidazolidine-trione-carboxylic acid derivatives as the active component, and to the use of the agent for regulating plants.



  metabolism, especially the regulation of fruit abscission and senescence.



   The agent is characterized in that it contains compounds of the formula I as the active component
EMI1.1
 contains. These can also be referred to as parabanic acid derivatives.



   In this formula: Rl: hydrogen denotes an alkyl, alkenyl, alkynyl, a cycloaliphatic or an alkoxycarbonyl, alkylthiocarbonyl, an alkyl radical substituted by cycloalkyl, alkoxy, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkylthio, dialkylamino or halogen, an alkenyloxyalkyl radical, a phenyl radical which is optionally substituted by halogen, nitro, lower alkyl, alkoxy, haloalkyl or cyano, the tetrahydro-3-thienyl-S, S-dioxide radical, a benzyl radical which is optionally substituted by halogen, nitro and / or lower alkyl - or phenethyl radical or a tetrahydrofurfuryl radical,
R2:

   an alkyl, alkenyl, alkynyl, a cycloaliphatic or an alkyl radical substituted by cycloalkyl, alkoxyalkoxycarbonyl, alkenyloxy, alkoxy or halogen, a phenyl radical optionally substituted by halogen, nitro, lower alkyl, haloalkyl or cyano, an optionally substituted by halogen, nitro and / or lower alkyl ring-substituted benzyl or phenylethyl radical or a furfuryl or tetrahydrofurfuryl radical,
Y: an oxygen or a sulfur atom. In this formula I, the possible addition salts with organic or inorganic acids are included.



   The compounds of the formula I thus represent la: (Y = O) carbon ester or Ib: (Y = S) carbon thioester.



   In formula I, alkyl radicals are preferably to be understood as meaning straight-chain or branched radicals having 1 to 18 carbon atoms, such as e.g. Methyl, ethyl, n-propyl, isopropyl. n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, n-decyl, n-undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and the like Isomers of the C5-C18 alkyl radicals. In particular the lower straight-chain and branched alkyl radicals, i. those with 1 to 6 carbon atoms can form the alkyl part of alkoxy, alkylthio or dialkylamino-substituted alkyl radicals or phenyl radicals.



  Haloalkyl radicals are preferably lower alkyl radicals with 1 to 4 carbon atoms, which can be substituted by fluorine, chlorine, bromine and / or iodine, e.g. Trifluoromethyl. B-fluoroethyl, p-chloroethyl, B-bromoethyl, B-iodoethyl, etc. In formula I, alkenyl radicals are generally understood to mean straight-chain or branched radicals with 3 to 18 carbon atoms, preferred are allyl, methallyl and Crotyl residue.



   These alkenyl radicals can be substituted one or more times by halogen, such as fluorine, chlorine, bromine and / or iodine. Alkynyl radicals preferably have 3 to 5 carbon atoms in a straight chain, propynyl and butynyl radicals, such as 2-propynyl or a propynyl radical substituted by lower alkyl, are preferred as cycloaliphatic radicals R1 and / or R2 are mono- and polycyclic cycloalkyl and cycloalkenyl radicals having 3 to 12 carbon atoms are preferred. Monocyclic cycloalkyl radicals, such as Cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclododecyl. These cycloalkyl radicals can also be substituted by lower alkyl radicals, e.g. by methyl, ethyl, n-propyl, isopropyl or n-butyl, tert-butyl, sec-butyl, isobutyl.



   Those compounds of the formula I in which Y is oxygen or sulfur and one of the two substituents R1 and R2 is an alkenyl radical and the other is an alkyl radical, or both substituents are an alkyl radical, have a particularly good effect that triggers the abscess of fruits, the number of carbon atoms of R1 and R2 together is between 3 and 6.



   The compounds of formula I are prepared, for example, by combining a urea of formula II R1-NHO N112 (II) with a functional derivative of oxalic acid, i. optionally with an oxalyl halide, preferably oxalyl chloride or oxalyl bromide, or with an oxalyl halide half ester, preferably oxalyl chloride lower alkyl ester (J. Prakt, Chemie [2] 32, 18) or with ehRem'oxalic acid lower alkyl ester to form a 2,4,5-trioxoimidazolidine derivative of the formula III
EMI1.2
 cyclized and this is then reacted with a halogen (thio) formic acid ester of the formula IV XCOYR2 (IV) wherein Y is an oxygen or sulfur atom, in the presence of an acid-binding agent.

  In the formulas II to IV, R1, R2 and Y have the meanings given under formula I and X is halogen, preferably chlorine or bromine.



   The conversion of the compounds of the formula III into those of the formula I can also be carried out in another way by reaction with a tert-amine. preferably a tert-alkylamine such as triethylamine to form salts of the formula V.
EMI1.3
 and reaction of these salts in a solvent with phosgene and further reaction of the chlorocarbamoyl compounds formed as intermediates, optionally (Ia) with an alcohol or phenol of the formula HO-R2 or (Ib) with a mercaptan of the formula HS-R2.



   The reactions are preferably carried out in the presence of solvents or diluents which are inert towards the reactants and at reaction temperatures in the range from 500 to +110.degree.



   The following solvents or diluents which are inert towards the reactants can be used: aliphatic and aromatic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, ethers and ethereal solvents such as dialydioxane ethers ; preferably halogenated alkanes such as methylene chloride, ethylene chloride, chloroform and carbon tetrachloride.



   Inorganic and organic bases can serve as acid-binding agents for this process. The reaction of a urea of the formula II with an oxyalkyl halide can take place in the presence of inorganic bases. For the introduction



  For the COYR2 group, an acid-binding agent in the form of an inorganic or organic base is required. The hydroxides, hydrogen carbonates and carbonates of alkali and alkaline earth metals, as well as the hydrides and amides of alkali metals, are suitable as inorganic bases. Tertiary amines and alkanolates can be used as organic bases, e.g. Trialkylamines, such as triethylamine, trimethylamine, pyridine and pyridine bases and the alkali metal alkanolates of lower alkanols, such as e.g. Sodium methylate, sodium ethylate, potassium ethylate, etc.



   The preparation of the imidazolidine-trionecarboxylic acid esters of the formula Ia can also be carried out by cyclizing an allophanic acid ester of the formula VI R1-NH-CO-NHOOR2 (VI) with an oxalyl halide such as oxalyl chloride or oxalyl bromide, and if R1 is hydrogen, further reaction of the compound of the formula formed
EMI2.1
 with a halide of the formula Rl-halogen (R1 = H) to achieve the desired end product. The reaction can be carried out in an inert solvent as indicated above or else in dimethylformamide.



   Allophane esters of formula VI can be prepared by known methods, e.g. by reaction of a chloroformyl urethane R2OCC-NH-CO-CI with an amine Rl-NH2 (Am. Chem. J. 19, 344) or, if R1 is an optionally substituted phenyl radical, by reaction of a chloroformanilide with a carbamic acid ester H2N -COOR2 (Am Chem. J. 19, 346). An isocyanate R1-N =C =O can also act on a carbamic acid ester H2N-COOR2 or its alkali salt (J. Am. Chem. Soc. 41, 1008). Allophanoic acid esters of the formula VI can also be obtained by transamidation of an allophanoic acid ester of the formula H2N-CO-NH-COOR2 at about 120-125 "C with an amine, preferably an aniline of the formula R1-NH2 (J. Am. Chem. Soc. 42, 2304).

  In some cases the reaction of a phenylurea of the formula R1-NH -CONH2 with dialkyl carbonate in a basic medium, e.g. in the presence of an alkali alcoholate (DRP.



   427,417).



   The imidazolidine derivatives of the formula I, in which the by
R1 having an amino group capable of forming addition salts can be converted into the corresponding addition salts by reaction with inorganic or organic acids in a manner known per se. For the formation of addition salts, e.g. the following acids into consideration: hydrohalic acids, such as
Hydrochloric and hydrobromic acid, also phosphoric acid, sulfuric acid, fluoroboric acid (HBF4), perchloric acid, alkyl sulfuric acids, such as methyl or ethylsulfuric acid, naphthoic acids, benzoic acid, halobenzoic acids,
Acetic acid, haloacetic acids such as trichloroacetic acid, amino acetic acid, propionic acid, halopropionic acids, butyric acid, lactic acid, stearic acid, aliphatic dicarboxylic acids such as oxalic acid, tartaric acid, maleic acid.



   The following examples illustrate the preparation process, further imidazolidine-3-carboxylic acid derivatives of the formula I, which are according to that described in the examples
Procedures prepared are found in the following
Table. The temperatures are given in degrees Celsius.



   Example 1 a) 88.1 g of ethylurea are suspended in one liter of tetrahydrofuran. At 100, add 85.2 ml slowly
Oxalyl chloride, stirring is continued for three hours at room temperature and then three hours under reflux. The suspension is filtered hot, the filtrate is evaporated and the residue is recrystallized from isopropanol. L-ethyl-2,4,5-trioxo-imidazolidine is obtained, which melts at 124-126.



   b) 11.5 g (0.5 mol) of sodium in 200 ml of abs. converted to sodium alcoholate. 44.05 g (0.5 mol) of ethylurea are introduced at room temperature and the mixture is stirred until a clear solution is obtained. With stirring, 73.01 g (0.5 mol) of diethyl oxalate are slowly added dropwise without external cooling, so that the reaction temperature is between 25
300C moves. Addition time approx. 1.5 hours. The mixture quickly becomes cloudy. After the addition has ended, the mixture is stirred for 1 hour at room temperature and 55 ml of conc.



   HCL too, so that the reaction temperature does not exceed 300C. After stirring for 1 hour, the mixture is filtered and the filtrate is concentrated until a thick, mushy mass is present, filtered off with suction, dried at 70 ° C. and the 1-ethyl -2,4,5-trioxoimidazolidine obtained recrystallized from isopropanol.



   c) 426 g of 1-ethyl-2,4,5-trioxo-imidazolidine are in 2.5
Liters of methylene chloride suspended. While cooling, first at 150,419 ml of triethylamine and then at 5 "-10,390 ml of isobutyl chloroformate are added dropwise. The mixture is stirred overnight at room temperature and then extracted three times with 500 ml of water. The organic phase is dried over magnesium sulfate and evaporated and the
Recrystallized residue from isopropanol. The received
1-Ethyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid isobutyl ester melts at 92 "-92.5".

 

   d) A solution of 11.7 g of isobutyl carbamate in 20 ml of absolute toluene is slowly added at -10 "to 0 to 3.64 g of a 55% strength sodium hydride dispersion in 50 ml of absolute toluene. Another half is stirred Hour further and then added dropwise at -10 "to + 100 7.9 ml of ethyl isocyanate. The mixture is left to stir overnight at room temperature and then acidified with 55 ml of ice-cold 2N hydrochloric acid.



   The organic phase is washed free of chlorine with water, dried over magnesium sulfate and evaporated. The oily residue of HGC2-NH-CO-NH-COOisoC4Hg is taken up in 100 ml of chloroform and the solution is added
6.82 ml of oxalyl chloride and can be stirred for a further two hours at room temperature and one hour under reflux.



  Now the chloroform is evaporated and the residue is recrystallized from isopropanol. The 1-ethyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid isobutyl ester obtained has a melting point of 910,930.



   Example 2
20.8 g (= 0.1 mol) of N'-phenylallophanoic acid ethyl ester (= 3-phenyl-urea-1-carboxylic acid ethyl ester), prepared according to Example 1d from phenyl isocyanate and carbamic acid ethyl ester in a basic medium, are placed in 200 ml of chloroform. To this, 8.55 ml (= 0.1 mol) of oxalyl chloride are added dropwise with slight ice-water cooling and, when the dropwise addition, the mixture is heated under reflux for 5 hours. The reaction mixture is then cooled in an ice bath, and white, crystalline 1-phenyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid ethyl ester precipitates from the clear solution. Together with the further amount obtained from the mother liquor, the end product is recrystallized from isopropanol. Melting point 162-1640.



   Example 3 a) 250.05 g (= 1.9 mol) of ethyl allophase acid, obtained by reacting disodium cyanamide salt with chlorine.



  ethyl formate and saponification of the NC-NH-COOC2H5 formed with conc. Sulfuric acid is obtained at about -10 C, are suspended in 2850 ml of benzene and heated to 55 C. 162.5 ml (= 1.9 mol) of oxalyl chloride are added dropwise over a period of 2 hours, the mixture is heated to 60 ° C. for a further 2 hours and the reaction mixture is allowed to react to completion for 3 hours by refluxing. On cooling, 318.4 g of imidazolidine-2,4,5-trione-3-carboxylic acid ethyl ester, melting point approx. 110 C.



   b) Add to a clear solution of 27.9 g (= 0.15 mol) of imidazolidine-2,4,5-trione-3-carboxylic acid ethyl ester in 60 ml of dimethylformamide (absolute.) 20.9 ml (= 0.15 Mol) of triethylamine are added dropwise, the mixture is stirred for 15 minutes and then 11.3 ml (= 0.15 mol) of freshly distilled propargyl bromide are rapidly added dropwise, the temperature rising to about 60.degree. The mixture is stirred overnight, the solvent is stripped off in vacuo, the residue is taken up in 250 ml of methylene chloride and washed 3 times with 50 ml of water. The separated methylene chloride phase is dried over Mg SO4 and concentrated.



  8.5 g of 1-propargyl-imidazolidine-2,4,5-trione-3-carboxylic acid ethyl ester, melting point 138-142 ° C. (ethanol) are obtained.



   The following table shows further compounds of the formula Ia
EMI3.1
 listed, which were prepared by the methods described in the preceding examples.



  Verb. Melting
No. R1 R2 point
1.1 H ethyl 1100 (decomp.)
1.2 methyl methyl 144-146
1.3 methyl ethyl 87-88
1.4 methyl 2-brondethyl 1100.1150
1.5 methyl 2thloroethyl 940
1.6 methyl allyl 76-78
1.7 methyl isopropyl 680- 710
1.8 methyl n-pentyl 640
1.9 methyl n-butyl 650-67
1.10 methyl isobutyl 98-99
1.11 methyl n -dodecyl 96-97
1.12 methyl phenyl 195 (decomp.)
1.13 methyl n-propyl 74-75
1.14 methyl benzoyl 125-128
1.15 methyl 4-nitrobenzyl 1870 (decomp.)
1.16 Ethyl 2-chloroethyl 1060-1080
1.17 ethyl methyl 102-104
1.18 ethyl n-amyl 65-68
1.19 ethyl ethyl 87 880
1.20 ethyl propyl 760-77
1.21

   Ethyl 2-bromoethyl 135-135.5
1.22 ethyl n-octadecyl 890- 910
1.23 ethyl allyl 81-82
1.24 ethyl propargyl 1140.1150
1.25 ethyl isopropyl 1000-101.50
1.26 ethyl 2-allyloxyethyl 55-57
1.27 ethyl n-butyl 68 -69
1.28 ethyl dodecyl 870- 890
1.29 ethyl phenyl 1720.1760
1.30 ethyl cyclohexyl 1010-1030
1.31 ethyl benzyl 1170.1180
1.32 ethyl tetrahydro. Oil furfuryl
1.33 phenyl methyl 186-190
1.34 ethyl isobutyl 92-92.5
1.35 ethyl p-tolyl 1520.1560
1.36 Ethyl sec.ButyI 720- 739
1.37 phenyl ethyl 163-165
1.38 phenyl 2-bromoethyl 198 (decomp.)
1.39 phenyl

     Allyl 1700 (decomp.) Conn. Enamel no. R1 R2 point
1.40 Phenyl Isopropyl 1840-1860
1.41 phenyl n-butyl 1590.1610
1.42 phenyl isobutyl 162-164
1.43 phenyl n-pentyl 1430-1460
1.44 phenyl n -dodecyl 145-150
1.45 phenyl phenyl 221-224
1.46 phenyl benzyl 202-205
1.47 Ethyl 2-Chlorophenyl Semicrist.



   1.48 n-Propyl n-Octadecyl 91-930
1.49 n-propyl propargyl 1070-1080
1.50 n-propyl isobutyl 85-880
1.51 isopropyl isobutyl 99 -102
1.52 n-butyl methyl 102-103
1.53 n-butyl 2-allyloxyethyl 75-76
1.54 n-butyl isobutyl 85-870
1.55 isobutyl n-pentyl 77-800
1.56 isobutyl isobutyl 980-1010
1.57 2. Ethylthioethyl propargyl 108.50.1090
1.58 2. Ethylthioethyl isobutyl 1150.1160
1.59 tert-butyl isobutyl 62-660
1.60 isopentyl isopropyl 70-740
1.61 methyl sec-butyl 94-960
1.62 n-octyl methyl 1110.1120
1.63 n-Octyl isobutyl 83-850
1.64 n-Dodecyl Allyl 990-1000
1.65 n-dodecyl isobutyl 87-900
1.66 n-dodecyl p-tolyl 149-152
1.67 n-Octadecyl ethyl 98-990
1.68 n-Octadecyl 2-Chlorophenyl 76-78
1.69 allyl

   Isobutyl 79.5-820
1.70 propargyl ethyl 138 -142
1.71 2-chloroethyl ethyl 128-130
1.72 sec-butyl isobutyl 32-360
1.73 isobutyl tetrahydro-88-91 furfuryl
1.74 2-methoxyethyl isobutyl 38-42
1.75 2-dimethylamino-allyl 43-46 ethyl
1.76 cyclopropyl isobutyl 1350.135.50
1.77 Cyclopropyl n-Octadecyl 1130.1150 Verb. Enamel no.

  R1 R2 point
1.78 cyclopropyl p-tolyl 1970.2000
1.79 cyclopentyl methyl 105 -106
1.80 Cyclopentyl Isobutyl 1170.1190
1.81 Cyclohexyl isopropyl 128-130
1.82 cyclohexyl isobutyl 130-132
1.83 cyclododecyl isobutyl 1040-1090
1.84 cyclododecyl benzyl 1220.1280
1.85 4-Cyclohexylbutyl tetrahydro. 77-790 furfuryl
1.86 4. Cyclohexylbutyl Isobutyl 112 -113
1.87 3-bromophenyl isopropyl 105-108
1.88 3. Bromophenyl Cyclohexyl 172-175
1.89 p-tolyl n-pentyl 136-140
1.90 p.tolyl 2-allyloxyethyl 136-139
1.91 3-trifluoromethyl-methyl 1800.1830 phenyl
1.92 2,5-dimethoxy-isobutyl 116-118 phenyl
1.93

   2,5-dimethoxy-propargyl 130-132 phenyl
1.94 benzyl ethyl 108.5-110
1.95 benzyl isobutyl 126-127
1.96 benzyl 3-chlorophenyl 167-170
1.97 4-chlorobenzyl n-octadecyl 1080-1100
1.98 4-chlorobenzyl p. Tolyl i720-1730
1.99 tetrahydrofurfuryl isobutyl 78-81
1,100 tetrahydro-3-thie-ethyl 157-160 nyl-s, s-dioxide
1.101 Tetrahydro.3-tbie isobutyl 1230.1270 nyl-s, s-dioxide
1.102 Tetrahydro-3-thie Benzyl 169-172 nyl-s, s-dioxide
1.103 -CH2COOCH2CHa Ethyl Semicrist.

 

   1,104 H isobutyl 122-125
1.105 2-methoxyethyl 2-chlorophenyl semicrist.



   1.106 2-methoxyphenyl isobutyl 1440.1460
1.107 Ethoxycarbonyl Benzyl Semicrist.



   1.108 Ethylthio-carbonyl Ethyl Semicrist.



   1.109 methoxycarbonyl ethyl semicrist.



   1,110 ethoxycarbonyl n-octadecyl approx. 900
1.111 Isobutoxycarbonyl Ethyl Semicrist.



   1.112 Benzyloxycarbonyl Isobutyl Semicrist
Example 4
71 g of 1-ethyl-2,4,5-trioxo-imidazolidine are suspended in 500 ml of methylene chloride. While cooling, 70 ml of triethylamine are first added dropwise at 150 and then 62.5 g of ethyl chlorothioformate at room temperature, the reaction temperature reaching up to the boiling range of the solvent. The reaction is completed by refluxing for 10 hours. After cooling to room temperature, it is extracted three times with 100 ml of water. The organic phase is dried over magnesium sulphate and evaporated, and the residue is recrystallized from isopropanol. The 1-ethyl-2,4,5-trioxoimidazolidine-3-thiocarboxylic acid-S-ethyl ester obtained melts at 123-124 with decomposition.



   Example 5 a) 272.3 g of N-phenylurea are in 1.51 tetrahydro.



  furan solved. The solution is warmed to 50 and slowly mixed with 171 ml of oxalyl chloride, the reaction temperature should not exceed 650. The mixture is stirred for a further hour at room temperature and then under reflux for four hours. The reaction mixture is evaporated and the residue is recrystallized from isopropanol. 1-phenyl-3,4,5-trioxo-imidazolidine is obtained, which melts at 214-216.



   b) 19 g of 1-phenyl-2,4,5-trioxo-imidazolidine are suspended in 100 ml of chloroform. While cooling, 14 ml of triethylamine are first added dropwise at 150 and then 15.3 g of S-sec.butyl chlorothioformate at room temperature. The mixture is stirred under reflux for 8 hours. After cooling to room temperature, it is extracted three times by shaking with 30 ml of water. The organic phase is dried over magnesium sulphate and evaporated, and the residue is recrystallized from isopropanol. The 1-phenyl "2,4,5-trioxo -imidazolidine-3-thiocarboxylic acid-S-sec.



  butyl ester melts at 150-152.



   The following table shows further compounds of the formula Ib
EMI5.1
 listed, which was prepared by the methods described in Examples 4 and 5 above.



   Verb. Rs R2 Melting point no.



   2.1 methyl ethyl 1050.1070
2.2 methyl allyl 1130.1150
2.3 methyl n-propyl 1090-1100
2.4 methyl isopropyl 95-980
2.5 methyl n-butyl 74-79
2.6 methyl sec-butyl 95-970
2.7 methyl tert-butyl 1120.1130
2.8 Ethyl Ethyl 1230.1240 Connection Rt R2 Melting point
No.



  2.9 Ethyl Allyl 119 -121 2.10 Ethyl n-Propyl 100 -102 2.11 Ethyl Isopropyl 99 -101 2.12 Ethyl n-Butyl 70 - 740 2.13 Ethyl sec-Butyl 72 -74 2.14 Ethyl tert-Butyl 91 - 930 2.15 Phenyl Ethyl 1380 ( Decomp.) 2.16 Phenyl Allyl 189 -190 2.17 Phenyl n-Propyl 148 (decomp.) 2.18 Phenyl Isopropyl 147 (decomp.) 2.19 Phenyl sec.-Butyl 1500.1520 2.20 Phenyl n-Butyl 1620 (decomp.) 2.21 Cyclopropyl Cyclohexyl 1550.1560 2.22 4Cyck > hexyl- isobutyl 83.5-860 butyl 2.23 methyl methyl 127-129 2.24 n-butyl isobutyl 43-450 2.25 isopropyl furfuryl 106-108 2.26 allyl methoxyethoxy semicrystalline carbonylmethyl 2.27 n-propyl sec-butyl 74 -77 2.28 isobutyl isobutyl 82 -85 129

   Ethyl l-phenethyl semicryst 2.30 allyl p-chlorobenzyl 2200.2250 2.31 allyl t-butyl semicryst 2.32 benzyl 2,4,4-trimethyl semicrystalline pentyl 2.33 isobutoxy-ethyl semicryst carbonyl 2.34 isobutoxy-methyl semicrystalline carbon79yl 2.35 ethoxycarbonyl isobutyl-semicrystalline 2.35 2-methoxy- cyclohexyl 1890.1920 phenyl 2.38 ethyl Z2-dimethyl- semicrystalline propyl 2.39 sec.

  Butyl 2,4,4-trimethyl semicrystalline pentyl 2.40 methyl n-octadecyl 1200.1220 2.41 sec.Butyl 2nd methoxyethyl semicrystalline 2.42 n-octadecyl n-octadecyl 111 -113 2.43 3-nitro-4-tolyl isopropyl 1380.1400
The following table shows new 2,4,5-trioxoimidazolidine derivatives of the formula III
EMI6.1
    summarized: R1 melting point n-propyl 1090 .1120
Isopropyl 95-97 n-butyl 96.5-99 tert-butyl 1190-1260 n-octyl 1050-1070 n-dodecyl 112-115
2-chloroethyl 119-121
2-methoxyphenyl 171-173
2-methoxyethyl 107-1080
2-dimethylaminoethyl.

  HCl 230-235
CycLopropyl 1550-1580
Cyclopentyl 1070-1100
Cyclododecyl ca 153
4-cyclohexylbutyl 86.5-91
4-chlorobenzyl 175-176
3-bromophenyl 235-237
3-trifluoromethyl-phenyl 180-182
2,5-dimethoxyphenyl 192-197
2-ethylthioethyl 88-90
Sulfolane 235-240
4-chlorophenyl 2350 3,4-dichlorophenyl 2310-2320
Tetrahydrofurfuryl 94 - 96 sec.Butyl semicrist
3,5-dichlorophenyl 215-217 3-nitro-4-methyiphenyl 1920-1950
The active ingredients of the formula I and their salts influence the growth of above and below ground parts of plants in various ways, they are not phytotoxic in the usual concentrations and have a low toxicity to warm blooded animals. The active ingredients do not cause any morphological changes or damage that would cause the plant to die.

  Their effect is different from that of a herbicidal active ingredient and a fertilizer.



   The new compounds influence vegetative plant growth and the formation of separating tissue. This makes fruit abscission much easier. This is of great economic importance for mechanical harvesting, e.g. of citrus fruits, apples, pears, peaches, cherries and other stone or pome fruits and olives.



   The following experiment shows the extent to which the removal of citrus fruits is facilitated.



   Example 6
Individual branches that bore at least 15-20 ripe fruits were sprayed on citrus trees of the specified variety with an active ingredient concentration of 0.4% or 0.2%.



  7 days after the application, the picking force of 10 fruits treated in the same way was determined with the aid of a spring-loaded balance and the mean value was formed from the 10 measured data [W.C. Wilson and C.H. Hendershott, Proc. At the. Soc.



  Hoard. Science, 90: 123-129 (1967)].



   In this test, the active substances of the formula I brought about the reductions in the picking forces shown in the table below. Three different types of oranges were tried:
1 = Valencia, tested in Florida,
2 = Pine apple, tested in Florida,
3 = Navel, tested in Spain.



   Concentration of active ingredient tration Kraft variety% in kg 1-methyl-2,4,5-trioxo-imidazoli- 0.2 3.1 2 din-3-carboxylic acid n-butyl ester 0.4 * 1-methyl-2,4, 5-trioxo-imidazoli- 0.2 2.6 2-dyne-3-carboxylic acid isobutyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazoli- 0.2 * 1 dyne-3-carboxylic acid isobutyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine -3-carboxylic acid benzyl ester 0.4 4.1 2 1-methyl-2,4,5-trixox-imidazoli- 0.2 6.1 1 din-3-carboxylic acid methyl ester 0.4 5.7 1-methyl-2,4,5-trioxo-imidazoli- 0.2 2.3 2 din-3-carboxylic acid ethyl ester 0.4 * 1-methyl- 2,4,5-trioxo-imidazolidine-3-carboxylic acid (2'-bromoethyl) ester 0.4 3.8 1 1-methyl-2,4,5-trioxo-imidazolinedin-3-carboxylic acid aliyl ester 0, 4 2.5 2 1-methyl-2,4,5-trioxo-imidazoli- 0.2 * 1 dyne-3-carboxylic acid isopropyl ester 0.4 * I.

   -Methyl; 2,4,5-trioxo-imidazolidine-3-carboxylic acid (4'-nitro-benzyl) ester 0.2 5.4 1 1-ethyl-2,4,5-trioxo-imidazolidine-0 , 2 6.1 1 -3-methyl carboxylate 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine 0.2 3.0 1 -3-ethyl carboxylate 0.4 *
Concentration active ingredient tration Kraft variety% in kg 1-ethyl-2,4,5-trioxo-imidazolidine 0.2 7.1 1-3-carboxylic acid (2'-bromoethyl) ester 0.4 5.8 1-ethyl -2,4,5-trioxo-imidazolidine-0.2 6.8 1 -3-carboxylic acid allyl ester 0.4 4.4 1-ethyl-2,4,5-trioxo-imidazolidine-0.2 7.9 1 -3-carboxylic acid isopropyl ester 0.4 7.4 1-ethyl-2,4,5-trioxo-imidazolidine 0.2 1,2 2 -3-carboxylic acid n-butyl ester 0.4 * 1-ethyl 2,4,5-trioxo-imidazolidine-0.2 7.0 1-3-carboxylic acid phenyl ester 0.4 6.2 1-ethyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid (2 ' chloroethyl) ester 0.4 6.4 3 1-phenyl-2,4,5-trioxo-imidazoli- 0.2 7.1 1

   din-3-carboxylic acid n-butyl ester 0.4 6.0 1-phenyl-2,4,5-trioxo-imidazolidine 0.2 7.5 1 -3-carboxylic acid isobutyl ester 0.4 7.4 1- Phenyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid benzyl ester 0.4 6.8 1 1-n-propyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid isopropyl ester 0.4 5 , 0 3 1-n-butyl-2,4,5-trioxo-imidazolinedin. 3. Carboxylic acid, methyl ester 0.4 7,0 3 1-n-butyl-2,4,5-trioxo-imidazolinedin-3 -carboxylic acid (2'-allyloxyethyl) ester 0.4 6.8 3 1-n-butyl-2,4,5-trioxo-imidazolinedine-3-carboxylic acid isobutyiester 0.4 6.6 3 1-isobutyl -2,4,5-trioxo-imidazolinedine-3-carboxylic acid isobutyl ester 0.4 5.7 3 1-n-octyl-2,4,5-trioxo-imidazolinedine-3-carboxylic acid methyl ester 0.4 6 , 9 3 1-n-octyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid isobutyl ester 0.4 6.8 3 1- (2'-chloroethyl) -2,4,5-trioxo-imidazolidine 3-carboxylic acid ethyl ester 0.4 7.0 3 1

   .Isobutyl-2,4,5.trioxo-imidazoli.



  din-3-carboxylic acid tetrahydrofuryl ester 0.4 6.3 3 1-Benzyl-2,4,5-trioxo-imidazolidin-3-carboxylic acid isobutyl ester 0.4 5.8 3 l-Meulyi-2A, S- trioxo-imicYazoli- 0.2 7.6 1-din-3-thiocarboxylic acid-S-ethyl ester 0.4 * 1-methyl-2,4,5-trioxo-imidazoli din¯3-thiocarboxylic acid-S-nipro- 0.2 4.0 1 pyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine-0.2 4.2 1 -3-thiocarboxylic acid Sn-propyl ester 0.4 * concentration K @@@ active ingredient tration in kg variety 1-phenyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid Sn-propyl ester 0.4 6,6 1 1-phenyl-2,4,5-trioxo-imidazolidine -3-thiocarboxylic acid- S-ethyl ester 0.4 6.6 1-methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-Sn-0.2 * 1 -butyl ester 0.4 * 1-ethyl-2,4,5 -trioxo-imidazolidine- 0.2 * 1 -3-thiocarboxylic acid Sn-butyl ester

   0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine -3-thiocarboxylic acid-S-isopropyl- 0.2 * 1 ester 0.4 * 1-methyl-2,4,5-trioxo-imidazolidine- 3-thiocarboxylic acid-S-isopropyl 0.2 * 1 ester 0.4 * 1-phenyl-2,4,5-trioxo-imidazolidine-0.2 7.2 1-3-thiocarboxylic acid-Sn-butyl ester 0.4 6 , 7 1-Ethyl-2,4,5-trioxo-imidazolidine-0.2 4.9 1 -3-thiocarboxylic acid S-ethyl ester 0.4 * 1-methyl-2,4,5-trioxo-imidazolidine-0 , 2 6.1 1 -3-thiocarboxylic acid S-allyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine 0.2 * 1 -3-thiocarboxylic acid S-allyl ester 0.4 * 1 -Phenyl-2,4,5-trioxo-imidazolidine- 0.2 7.1 1 -3-triocarboxylic acid-S-allyl ester 0.4 6.6 1-methyl-2,4,5-trioxo-imidazolidine- 0, 2 * 1 -3-thiocarboxylic acid-S-sec-butyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine-0.2 * 1 -3-thiocarboxylic acid-S-sec-butyl ester 0.4 * 1-methyl-2,4,5-trioxo-imidazolidine-0.2 * 1 -3-thiocarboxylic acid S-tert.butyl ester 0.4 * 1-ethyl-2,4,5-trioxo-imidazolidine-0.2 *

   1 -3-thiocarboxylic acid-S-tert-butyl ester 0.4 * control - 8.5 1
The fruits hanging on the tree could be easily removed.



   men that no measurement could be made.



   Example 7
Attempts to inhibit senescence a) Keeping cut flowers fresh
Roses of the variety Dr. Verhagen (import from Holland) were used as test flowers. They were placed in the corresponding test solutions and placed in the climatic chamber at constant temperature (approx. 230C) and at rel. Humidity of approx. 80% kept. Her condition was assessed daily. The table shows up to how many days the flowers can be kept without losing petals or showing signs of wilting.



   The active ingredients were not tested directly in the water but in a pH 3.4 buffered basic solution, which e.g. contained a fungicide like Irgasan
3 roses each were in a container and 3 containers each received the same solution. The shelf life in the basic solution without active ingredient is given as a comparison. The active ingredients were usually added in a formulated form as wettable powder in a concentration of 50 ppm.



     
Conc. Shelf life active ingredient: ppm in days 1-Methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-Sn-propyl ester 50 7 1-Methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S -isopropyl ester 50 9 1-methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S-sec.-butyl ester 50 9 1-methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S- tert-butyl ester 50 9 1-ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid S-ethyl ester 50 7 1-ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid S-allyl ester 50 7.5
1-Ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid S-n-butyl ester 50 7
1-Ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S-sec.-butyl ester 50 7.5 1-Ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S-tert. butyl ester 50 4 1-phenyl-2,4,5-trioxo-imidazolidine-3 <RTI

    ID = 8.6> -thiocarboxylic acid S-ethyl ester 50 6 1-phenyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S-nMpropyl ester 50 6.5 1-phenyl-2,4,5-trioxo-imidazolidine -3-thiocarboxylic acid skisopropyl ester 50 9 1-phenyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid-S-al-diyl ester 50 5 1-phenyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid Se -butyl ester 50 7 Control: H20 (pH 3.4+ fungicide) - 3 b) Keeping cut Sinapis branches fresh
Mustard plants (Sinapis alba) are grown in plastic bowls with compost soil at 22 C and exposure to light for 16 hours per day (= approx. 5000 lux).

  Freshly cut branches 12-15 cm long from 4-week-old plants with green leaf buds are used for the freshness test. The branches are placed individually in beakers with graduated concentrations of active ingredient, which are obtained by dissolving various amounts of a 25% wettable powder. For 14 days, the branches are kept in the jars at 230C and 70% relative air humidity with exposure to light for 16 hours per day (= approx. 10,000 lux).



   The experiment is repeated once.



   The following results were obtained, based on the following graded evaluation: Rating 9 = strong yellowing of the leaves (control) Rating 1 = fresh green leaves
D = pronounced dark green color of the leaves
I = intense green color
Q = flowering delay 50 20 10 5
Active ingredient ppm ppm ppm ppm 1-phenyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid 1 4 7 8 -methyl ester DD 1 -ethyl-2,4,5-trioxo-imid-azolidine-3-carboxylic acid- 4 6 6 4 -ethyl ester DQ II DQ 1-ethyl-2,4,5-trioxo-imide azolidine-3-carboxylic acid iso- 7 7 5 5 butyl ester I IQ DD 1 -phenyl.2,4,5-trioxo- imidazolidine-3-carboxylic acid n- 7 7 6 8 -butyl ester ID 1 1

     1-phenyl-2,4,5-trioxo- imidazolidine-3-thiocarboxylic acid-Sn-propyl ester D DQ 1 1-methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid 6 6 7 5 -S-isopropyl ester DQ DID 1 -methyl-2,4,3-trioxo-imid-azolldin-3-thiocarboxylic acid 3 4 6 8 -S-sec.butyl ester DQ DD 1-benzyl-2,4,5 -trioxo-imidazolidine-3-carboxylic acid iso- 6 8 6 8 butyl ester II DQ 1-dodecyl-2,4,5-trioxo-imid azolidiu-3-carboxylic acid iso- 3 6 7 6 butyl ester DQ I DQ
The extent and nature of the effect depend on various factors, including the application concentration and the time of application in relation to the stage of development of the plant.

  However, these factors differ depending on the type of plant and the desired effect. So you are, for example, plants whose fruits are used or. are recycled, treat immediately after flowering or at an appropriate distance before harvest.

 

   The active ingredients are applied in the form of solid or liquid compositions both to above-ground parts of plants and in or on the ground. Preference is given to application to the above-ground parts of the plant, for which solutions aqueous dispersions are best suited. In addition to solutions and dispersions, dusts, granulates and grit are also suitable for treating the culture medium.



   The agents according to the invention are prepared in a manner known per se by intimately mixing and grinding active ingredients with suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients. The active ingredients can be present and used in the following working-up forms: solid working-up forms: dusts, scattering agents, granules, coated granules, impregnation granules and
Homogeneous granules; Active substance concentrates dispersible in water: wettable powders, pastes, emulsions; Liquid preparation forms: solutions.



   The active ingredients are mixed with solid carriers for the production of solid forms (dusts, grit, granules). Carriers include kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, Fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark meal, wood flour, nut shell meal, cellulose powder, residues from plant extractions, activated carbon, etc., each individually or as mixtures with one another,
The grain size of the carrier materials is expediently up to 0.1 mm for dust and approx.

   0.075 to 0.2 mm and for granules 0.2 mm or more.



   The active ingredient concentrations in the solid work-up forms are 0.5 to 80%.



   These mixtures can also be added to stabilize the active ingredient and / or nonionic, anion-active and cation-active substances, which, for example, improve the adhesion of the active ingredients to plants and parts of plants (adhesives and adhesives) and / or better wettability (wetting agents) and dispersibility (dispersants ) guarantee.

  Suitable adhesives include, for example, the following: olein-lime mixture, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols with 5-15 ethylene oxide residues per molecule and 8-9 carbon atoms in the alkyl residue, ligninsulphonic acid, its alkali and alkaline earth salts , Polyethylene glycol ether (Carbowaxe), fatty alcohol polyglycol ether with 5-20 ethylene oxide residues per molecule and 8-18 carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, propylene oxide, polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea-formaldehyde and latex products.



   Active ingredient concentrates dispersible in water, i.



  Wettable powders, pastes and emulsion concentrates are agents that can be diluted with water to any desired concentration. They consist of active ingredient, carrier, optionally additives stabilizing the active ingredient, surface-active substances and anti-foaming agents and optionally solvents. The concentration of active ingredients in these agents is 5-80%.



   The wettable powders and pastes are obtained by mixing the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous and grinding. Suitable carriers are, for example, those mentioned above for the solid work-up forms. In some cases it is advantageous to use mixtures of different carriers.

  The following can be used, for example, as dispersants: condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, and alkali metal, ammonium and alkaline earth metal salts of ligninsulfonic acid, further alkylarylsulfonates, alkali metal and alkaline earth metal salts , Fatty alcohol sulfates, such as salts of sulfated hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleyl methyl tauride, ditertiary acetylene glycols, di alkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts.



   Silicones, for example, can be used as antifoam agents.



   The active ingredients are mixed, ground, sieved and passed with the additives listed above in such a way that the solid portion of the wettable powders does not exceed a particle size of 0.02 to 0.04 and, in the case of the pastes, 0.03 mm.



  To produce emulsion concentrates and pastes, dispersants such as those listed in the previous sections, organic solvents and water are used. Examples of suitable solvents are the following: alcohols, benzene, xylenes, toluene, dimethyl sulfoxide, N, N-dialkylated amides, N-oxides of amines, especially trialkylamines, and mineral oil fractions boiling in the range from 1200 to 35.0 ". The solvents must be practically odorless, not phytotoxic, inert to the active ingredients and must not be easily combustible.



   The agents according to the invention can also be used in the form of solutions. For this purpose, the active ingredient or several active ingredients are dissolved in suitable organic solvents, solvent mixtures, water or mixtures of organic solvents with water.Aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkylnaphthalenes, mineral oils alone or as a mixture can be used as organic solvents. The solutions should contain the active ingredients in a concentration range of 1 to 20%.



   These solutions can be applied either with the help of a propellant gas (as a spray) or with special syringes (as an aerosol).



   Other biocidal active ingredients or agents can be admixed with the agents according to the invention described. Thus, in addition to the compounds of general formula I mentioned, the new agents can contain, for example, insecticides, fungicides, bactericides, fungistatic agents, bacteriostatic agents or nematocides to broaden the spectrum of action. The agents according to the invention can also contain plant fertilizers, trace elements, etc.



   Work-up forms of the new active ingredients are described below. Parts mean parts by weight.



  granules
The following substances are used to produce a 5% granulate:
5 parts of 1-xthyte2,4,5-tFiuxo-imidazodine-3-thlocarboxylic acid S-n-butyl ester.

 

      0.25 part of epichlorohydrin, 0.23 part of cetyl polygot rither,
3.50 parts of polyethylene glycol.



  91 parts of Kaoldn (grain size 0.3-0.8 mm).



   The active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and the acetone is then evaporated in vacuo.



     Wettable powder
To produce a) 40% b) 50%, c) 25% and d) 10% wettable powder, the following stocks are required.



     partevmm> (iet a) 40 parts of 1-ethyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid methyl ester
5 parts of lignin sulfonic acid sodium salt.



   1 part dibutyl naphthalenesulfonic acid sodium salt,
54 parts of silica; b) 50 parts of 1-methyl 2,4,5-trioxo-imidazoli'dinH3-thiocarboxylic acid, tert, butyl ester
5 parts of alkylarylsulfonate (Tinovetin B),
10 parts calcium ligrinsulfonate,
1 part champagne chalk - hydroxyethyl cellulose - mixture (1: 1),
20 parts of silica,
14 parts of kaolin; c) 25 parts of 1-ethyl-2,4,5-trioxo-imidazolidine-3-carboxylic acid isobutyl ester
5 parts of oleyl methyitauride sodium salt,
2.5 parts of naphthalenesulfonic acid-formaldehyde condensate,
0.5 parts of carboxymethyl cellulose,
5 parts of neutral Kal! Ïum-aluminum-silicate,
62 parts of kaolin;

   d) 10 parts of 1-methyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid S-allyl ester
3 parts mixture of the sodium salts of saturated
Fatty alcohol sulfates,
5 parts of naphthalenesulfonic acid-formaldehyde condensate,
82 parts of kaolin.



   The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. This gives spray powder which can be diluted with water to form suspensions of any desired concentration.



  Emulsion concentrate
To produce 25% emulsion concentrates, a) 25 parts of 1-ethyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid S-n-propyl ester
5 parts of a mixture of nonylphenol polyoxyethylene and calcium dodecylbenzenesulfonate,
70 parts of xylene, b) 25 parts of 1-phenyl-2,4,5-trioxo-imidazolidine-3-thiocarboxylic acid n-butyl ester
10 parts of a mixture of nonylphenol polyoxyethylene and calcium dbdecyl benzosulfonate,
65 parts of cyclohexanone mixed together. This concentrate can be diluted to suitable concentrations with water to form emulsions. Such emulsions are suitable for thinning flowers and fruits, for accelerating the ripening of fruits and for promoting fruit and leaf detachment.

 

   Instead of the active substances mentioned in the preparation examples for granules, wettable powders and emulsion concentrates, the other compounds encompassed by formula I can also be used.

 

Claims (1)

PATENT CLAIMS I. Agent for regulating plant metabolism, characterized in that it contains at least one imidazolidintrione-carboxylic acid derivative of the formula I as the active component EMI10.1 in the R1 is hydrogen, alkyl, alkenyl, a cycloaliphatic radical or an alkoxycarbonyl or alkylthio-carbonyl radical, an alkyl radical substituted by cycloalkyl, alkoxy, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkylthio, dialkylamino or halogen, an alkenyloxyalkyl radical, an optionally substituted by halogen, nitro, lower Alkyl, alkoxy, haloalkyl or cyano-substituted phenyl radical, the tetrahydro-3-thienyl-S, S-dioxide radical, a benzyl or phenylethyl radical optionally ring-substituted by halogen, nitro and / or lower alkyl or a tetrahydrofurfuryl radical, R2 is an alkyl, alkenyl, alkynyl, a cycloaliphatic or one by cycloalkyl, Alkoxyalkoxycarbonyl, alkenyloxy, alkoxy or halogen-substituted alkyl radical, a phenyl radical optionally substituted by halogen, nitro, lower alkyl, haloalkyl or cyano, a benzyl or phenylethyl radical optionally substituted by halogen, nitro and / or lower alkyl, or a furfuryl or Tetrahydrofurfuryl residue, Y denotes an oxygen or sulfur atom, or contains at least one addition salt thereof with an organic or inorganic acid. II. The use of the agent according to claim I for regulating the plant metabolism. SUBCLAIMS 1. The use according to claim II for regulating fruit abscission, characterized in that plants with fruits that are about to be harvested are treated by direct application or by soil application. 2. The use according to claim II for inhibiting senescence on plants. Note from the Federal Office for Intellectual Property: If parts of the description are not in accordance with the definition of the invention given in the patent claim, it should be remembered that according to Art. 51 of the Patent Act, the patent claim is decisive for the material scope of the patent.