HU184120B - Compositions for determining growth of plants containing thiose micarbazide derivatives and process for producing the active agents - Google Patents

Abstract

The present invention relates to a method for the preparation of plant growth regulators and to the preparation of novel 1-benzoyl-3-thiosemicarbazide derivatives used as active ingredients therein. The agents of the present invention contain from 0.1 to 80% by weight of the new 1-benzoyl-3-thiosemicarbazide derivatives of formula (I), optionally as salts. Wherein R is -COR1 or hydroxymethyl; R 2 is C 1-4 alkyl, nitro, trifluoromethyl or halogen; Ar naphthyl, benzyl, C 1-4 alkylbenzyl or a group of formula (a), m is 0, 1 or 2; R 3 is hydrogen, C 1 -C 4 unsaturated C 1-4 alkyl, C 3-4 alkenyl, C 1-4 hydroxyalkyl, phenyl or benzyl; and R 4 is hydrogen or C 1-4 alkyl. Pesticides can be used to control both plant growth and weed control. O II Η “Ν — N — C — N —Ar -1-

Description

FIELD OF THE INVENTION This invention relates to plant growth regulating compositions and to processes for the preparation of novel 1-benzoyl-3-thiosemicarbazide derivatives as active ingredients.

U.S. Patent 4,026,903 discloses substituted thiosemicarbazides having antimicrobial activity which contain a 5-nitroimidazole group.

The agents according to the invention contain from 0.1 to 80% by weight of the novel 1-benzoyl-3-thiosemicarbazide derivatives of the formula (I), optionally in the form of salts. In this formula:

R is -COR * or hydroxymethyl,

R ^{1 is} hydroxy, -NR ', R', C 1 -C 12 alkoxy, C 1 -C 6 haloalkoxy, phenyl (C 1 -C 4 alkoxy), (C 1 -C 4 alkoxy) - , (C 1 -C 4 alkoxy) or (C 1 -C 4 alkoxy), (C 1 -C 4 alkoxy) - (C 1 -C 4) alkoxy, - H, (C 1 -C 12) alkyl, C 6 -cycloalkyl or phenyl-C 1 -C 4 -alkyl, wherein the phenyl is C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, (C 1 -C 6) -alkoxy - (C 1 -C 6) alkyl - or substituted with (C 1 -C 4) alkoxy (C 1 -C 4) -alkoxy, (C 1 -C 4) -alkyl;

R 'is hydrogen or C 1-6 alkyl, or

- R 'and R' together with the nitrogen atom to which they are attached form piperidyl,

R ^{2 is C} 1-4 alkyl, nitro, trifluoromethyl or halogen;

Ar is naphthyl, benzyl, C 1-4 alkylbenzyl or a group having the formula (a)

- R ^{5 is C} 1 -C 4 alkyl or halogen, provided that both ortho positions cannot be substituted by alkyl;

- R ^{6 is C} 1-4 alkylthio, nitro, C 1-4 alkoxycarbonyl, benzyloxy, di- (C 1-4) alkylamino or C 1-4 alkoxy or trifluoro; methyl;

- n is 0,1,2 or 3;

q is 0 or 1, provided that the sum of n and q is not more than 3; m is 0,1 or 2;

R ^{3 is} hydrogen, (C 1 -C 4) -alkyl, (C 3 -C 4) -alkenyl, ex, - (C 1 -C 4 -hydroxyalkyl, phenyl or benzyl) containing 2 unsaturations, and

R ^{4 is} hydrogen or C 1-4 alkyl.

The compositions of the present invention may also contain agriculturally acceptable salts or esters of these compounds as active ingredients.

Preferred active ingredients of the plant protection products of the present invention are those wherein, in formula (I): - R is carboxyl;

- m is 0;

- R ³ is hydrogen or C 1-4 alkyl; and

Ar is phenyl or benzyl, each of which may be substituted as above.

A further preferred group of such compounds are those compounds of formula (I) wherein Ar is phenyl or phenyl substituted by fluorine, chlorine or bromine, methyl, benzoyloxy, methoxy or trifluoromethyl.

The most preferred R ³ substituent is methyl.

Another preferred group of active compounds of formula (I) are those having the formula

SHE

II - R are -C-OH;

- Irish. is O;

- R ^{3 is} hydrogen or methyl;

- R ^{4 is} hydrogen;

- Ar (a);

n is 0 or 1; and q is 0.

Also agriculturally acceptable salts and esters of these compounds are valuable as active ingredients in the plant protection products of the present invention.

A preferred group of active ingredients in the pesticides of the present invention are also compounds of formula Ia wherein R ^{13 is} hydrogen or C 1-4 alkyl;

or their agriculturally acceptable salts or C 1 -C 4 alkyl esters.

Preferred formulations are those containing the active compounds of the formula (IB):

- R ⁷ is -OH or -NR "R"";

- R and R are hydrogen or methyl; - R ^{8 is} hydrogen, methyl or nitro, chloro or fluoro;

- R ^{9 is} hydrogen, (C 1 -C 4) -alkyl, ex (C 3 -C 4 -alkenyl without i-unsaturation or benzyl);

- Ar is a naphthyl or methyl benzyl group or a phenyl group containing from 1 to 3 methyl or methoxy groups, bromine, chlorine or fluorine atoms or trifluoromethyl groups, with the proviso that the phenyl group is ortho 3

Position -2184-120 cannot be substituted with methyl; and

- R ^{10 is} hydrogen, (C 1 -C 3) alkyl, (C 1 -C 12) alkyl, (C 1 -C 6) haloalkyl, or (C 1 -C 4) alkoxy (C 1 -C 4) alkyl, or sodium, potassium, , lithium or ammonium salts or other agriculturally acceptable salts thereof.

Other preferred active compounds are those compounds of formula (I)

R -CH ₂ OH; - R ³ hydrogen or (1-4C) alkyl; - m is 0; - R ⁴ hydrogen; and - Ar naphthyl or a compound of formula (a) or (b).

Salts which may be used as active ingredients in the plant protection products of the invention include metal salts, ammonium salts, quaternary ammonium salts and amine salts.

The 1-benzoyl-3-thiosemicarbazides of formula (I) are prepared by reacting a compound of formula (II) with a phthalic acid derivative of formula (III) or (IV). In the formulas (II) and (IV), R ¹ , R ² , R ³ , R ⁴ and m are as defined above and X is an easily cleavable group, preferably a halogen such as chlorine.

It is very advantageous to carry out this reaction in a homogeneous medium. An organic solvent is preferred which is capable of solubilizing both materials involved in the reaction. Suitable organic solvents include polar organic solvents such as chloroform, ethylene dichloride, isopropanol, dioxane, 1,2-dimethoxyethane, dimethylformamide, and methylene chloride.

The reaction is usually carried out at a temperature of -40 ° C to 100 ° C, with a preferred temperature range being from room temperature to 50 ° C.

Some of the intermediates of formula (II) are novel compounds.

The free acids of formula (I) may be converted into salts or esters. For the formation of salts, the acid is neutralized with a suitable base in a conventional manner. For example, the potassium salt may be prepared by reacting the free acid with KOH in isopropanol. In general, any inert solvent that will adequately dissolve at least one of the reactants will be used. Suitable neutralization temperatures are in the range of -40 ° C to 100 ° C. Preferably, the neutralization is carried out at a temperature ranging from room temperature to 50 ° C. During the neutralization, metal salts, ammonium and quaternary ammonium salts may be formed, but also amine salts such as pyridine or diethylamine salts may be prepared.

Compounds of formula II, R ⁴ hydrogen, may be prepared by reacting a suitable isothiocyanate derivative of formula V with a hydrazine derivative of formula h ₂ n-nhr ³ at a temperature between 0 ° C and 50 ° C. in an organic solvent, such as toluene, which is capable of solubilizing both reaction partners to an appropriate degree. This method is described in Acta Chemica Scandinavica, 22 (1), 1 (1968).

Compounds of formula II wherein R ^{4 is} other than hydrogen may be prepared by reacting N-alkyl-N-arylthiocarbamyl chloride of formula VI

The reaction is carried out with a hydrazine derivative of the formula H ₂ N NHR ³ .

The starting materials are reacted in an inert organic solvent such as diethyl ether and at a temperature in the range of 0 to 50 ° C, preferably at room temperature.

Compounds of formula (VI) may be prepared as described in Chemical Abstracts, 58, 4543. In the preparation, the amine of formula ArNHR ⁴ is reacted with thiophosgene in an ether-type solvent under anhydrous conditions ranging from 0 ° C to room temperature.

Compounds of formula I wherein R-COR ¹ and R ¹ are -NR R 'are prepared by reaction of the corresponding methyl ester (R = -COOMe) with an amine of formula HNR R at room temperature.

The methyl esters of formula I (R = -COOMe) may also be used to prepare the corresponding hydroxymethyl derivatives (R = CH ₂ OH). Thus, the methyl esters can be reduced to the corresponding hydroxymethyl derivatives with reducing agents, in particular sodium borohydride (NaBH ₄ ). This reduction is preferably carried out at a temperature in the range of 0 ° C to 50 ° C and especially at a temperature in the range of 5 ° C to room temperature. Suitable organic solvents are alkanols, such as ethanol.

/. Intermeric Preparation Example: Preparation of methyl hydrogen phthalate

Methanol (300 mL) was added in one portion to phthalic anhydride (148 g, 1.00 mol). The resulting suspension is stirred and refluxed for 36 hours. During heating, the mixture becomes a solution. The solvent was removed and the product was recrystallized from ethyl acetate-hexane. 114.6 g of the title compound are obtained (Literature: Beilstein, 9,797, mp 82.5-84 °).

Intermeriate Preparation Example 2: Preparation of methyl phthaloyl chloride

Methyl hydrogen phthalate (110.0 g, 0.611 mol) and thionyl chloride (77.4 g, 0.650 mol) were stirred in chloroform (200 ml) and the temperature was kept at 30 ° C. The mixture was then stirred for two hours at room temperature,

Heat to reflux for 5 hours. The solvent was evaporated under reduced pressure and the resulting crude product (120.9 g) was used without further purification (Beilstein, 9,797, non-constant).

Intermeric Preparation Example 3: Preparation of 2,4-Dimethyl-4-phenyl-3-thiosemicarbazide

To a solution of N-methyl-N-phenylthiocarbamyl chloride (79.6 g, 0.43 mole) in dry ether (250 mL) was added dropwise methylene chloride (39.5 g, 0.86 mole) at a temperature below 10 ° C. of hydrazine in 100 ml of dry ether. The reaction temperature was allowed to rise to room temperature and then the mixture was stirred. The filtrate was concentrated to a small volume and diluted with about 300 mL of hexane. The mixture was stirred for several hours and then the hexane layer was decanted. The hexane-immiscible layer was evaporated again to remove the organic solvent to give 70.0 g of the desired product as an orange dense liquid.

Intermediate Preparation Example 4: Preparation of 4-methyl-4-phenyl-3-thiosemicarbazide

To a solution of anhydrous hydrazine (7.7 g, 0.24 mol) in dry ether (200 ml) was added N-methyl-N-phenylthiocarbamyl chloride (20.4 g, 0.11 mol) at a temperature below 5 ° C. The mixture was stirred and allowed to warm to room temperature. The mixture is filtered and the residue is resuspended in about 100 ml of water. The suspension is stirred and then given birth. This gave 8.8 g of the desired product as an off-white powder.

121-122 ° C.

Intermediate Preparation Example 5: Preparation of 1-amino-3- (2-naphthyl) thiourea

In a round-bottomed flask, 1.1 g (0.035 mol) of anhydrous hydrazine was dissolved in 150 ml of diethyl ether. 4.6 g (0.25 mol) of 2-naphthyl isothiocyanate are then added dropwise and the temperature of the vessel is kept below 30 ° C during the addition. After stirring overnight at room temperature, the reaction mixture was cooled and the title product was isolated by filtration and then air-dried. 4.5 g of product are obtained.

174-176 ° C.

Intermediate Preparation Example 6: Preparation of 2-benzyl-4-phenyl-3-thiosemicarbazide Benzylhydrazine (0.0245 mole) and phenyl isothiocyanate (33.1 g, 0.0245 mole) were dissolved in isopropanol (200 mL) and the solution was 0-5. After cooling to 33.1 g (0.0245 mole) of phenyl isothiocyanate in 50 ml of light petroleum and a solution of it is added dropwise. During this step, the title compound precipitates out of solution. After addition, the reaction mixture was stirred at 40-45 ° C for one hour and the title compound was isolated by filtration as a white powder. 43 g of product are obtained.

121-123 ° C.

The following examples illustrate the preparation of compounds of formula (I).

Example 2 (2-Carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide

A solution of 2-methyl-4-phenyl-3-thiosemicarbazide (45.3 g, 0.25 mol) and pyridine (19.8 g, 0.25 mol) in 1,2-dimethoxyethane (800 ml) was stirred at room temperature and added dropwise. A solution of 49.8 g (0.25 mol) of methyl phthaloyl chloride in 100 ml of 1,2-dimethoxyethane was added over two hours. The resulting reaction mixture was stirred for 16 hours at room temperature. At the end of this period, the contents of the vessel are poured into ice water. The resulting solid was collected to give 73.3 g (85%) of product.

153.5-154 ° C.

Example 2 1- (2-Carbomethoxybenzoyl) -2-isopropyl-4-phenyl-3-thiosemicarbazide

0.25 mol of 2-isopropyl-4-phenyl-3-thiosemicarbazide prepared by reacting isopropyl hydrazine with phenyl isocyanate according to Acta Chem. Scand. 22, (1), (1968), further 0.25 moles of pyridine are dissolved in 125 ml of dimethoxyethane and transferred to a 300 ml 3-necked flask fitted with a dropping funnel and a thermometer. The solution was cooled to 10-15 ° C and 0.25 mol of methyl phthaloyl chloride dissolved in 25 ml of dimethoxyethane were added dropwise. The reaction mixture was stirred overnight at room temperature and the next morning poured into ice water. At this time, the title product precipitated as a solid which was rinsed with hexane and ethyl acetate which did not require further purification. 15.4 g of product are obtained.

Op.145-147 ° C.

Example 3 1- (2-Carbomethoxybenzoyl) -4-phenyl-3-thiosemicarbazide

The procedure described in Example 2 was followed to obtain the title compound. The resulting solid was rinsed with hexane and ethyl acetate. The product obtained does not require further purification. Yield 87%.

140-142 ° C.

Example 4 1- (2-Carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide

0.2 M 2-methyl-4-phenyl-3-thiosemicarbazide was dissolved in 5

The solution is placed in a 3-necked round-bottomed flask equipped with a magnetic stirrer, reflux condenser, additional powder funnel, and a thermometer. Then, 0.2 mol of phthalic anhydride was added at 20 ° per portion. The mixture was stirred overnight at room temperature and then poured into ice water the next morning. The resulting solid title product is recrystallized from hexane / ethanol. Yield 70%.

155-156 ° C.

Example 5

- (2-carboxybenzoyl) -4-phenyl-3-thiosemicarbazide

The device described in Example 4 was used and worked as described there. After adding all the phthalic anhydride, the mixture was heated at 80 ° for about 3 hours. The reaction mixture was then cooled and poured into ice water to give the title compound as a solid. This solid was rinsed with hexane / ethanol. Yield: 66%.

149-151 ° C.

Example 6

- (2-carboxy-benzoyl) -2-methyl-4-phenyl-3-tioszemikarbazidnátriumsó

The free acid prepared in Example 4 is suspended in methanol and placed in a 300 ml round-bottomed flask equipped with a magnetic stirrer and a reflux condenser. Sodium methoxide is then suspended in methanol and the suspension is transferred to the reaction vessel. The reaction mixture is stirred at room temperature for 30 minutes, during which time all solids are dissolved.

The reaction mixture was then evaporated to give the title compound. Yield 7.6 g.

195-197 ° C (dec.).

Example 7 1- (2-Carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazidammonium salt

The free acid prepared according to Example 4 is suspended in 100 ml of ethanol and the suspension is placed in a 300 ml round-bottomed flask equipped with a magnetic stirrer and a reflux condenser. Dimethoxyethane (20 mL) was added to the slurry to bring the compound into solution. After most of the solid had dissolved, NH ₄ OH was added. Meanwhile, no noticeable heat develops. The solvent was evaporated and the resulting solid (the title product) was heated to reflux in hexane / ethanol and then filtered. 4.3 g of product are thus obtained.

165-166 ° C.

<?. example

- (2-carbo-isopropoxy-benzoyl) -2-methyl-3-thiosemicarbazide 4fenü

To a solution of 5.0 g (0.014 mol) of 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide in 75 ml of isopropyl alcohol was added 1.0 g (0.014 mol) of tert-butyl aroin and the solution is stirred at room temperature for 16-18 hours. Most of the isopropyl alcohol was removed under reduced pressure, water was added to the residue and the resulting precipitate was collected. The title product thus obtained had a melting point of 115-117 ° C.

Example 9

2-Benzyl-1- (2-carboxybenzoyl) -4-phenyl 3-thiosemicarbazide

3.7 g (0.25 mol) of phthalic anhydride and 6.43 g (0.25 mol) of 2-benzyl-4-phenyl-3-thiosemicarbazide are dissolved in 100 ml of dimethylformamide and the solution is heated at 90 ° for 3 hours. . The solution was then cooled and poured into ice water with stirring. The title compound was filtered off as a solid and recrystallized. This gives a melting point of 140-142 ° C.

Example 10

1Y 2-Carboxybenzoyl) -2-methyl-4-phenyl-3-isosemicarbazide potassium salt g (0.182 mol) of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide is dissolved in slurry) in 400 ml of ethanol. Dissolve 10.2 g of potassium hydroxide in 200 ml of ethanol and add the solution to the acid-ethanol mixture. The ethanol is then evaporated until a crystalline product precipitates. 51 g of the title compound are obtained.

Mp 182-183 ° C.

Example 11

2-Dimethylaminocarbonyl-benzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide g (0.148 mol) 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide in aqueous dimethylamine suspended. The pH of the suspension is adjusted to about 3. A sticky precipitate formed which solidified after addition of diethyl ether. The solid title product is isolated. Yield 3.7 g, m.p. 140-143 ° C.

Example 12

- (2-Hydroxymethylbenzoyl) -2-methyl-4- (3-fluorophenyl) -3-thiosemicarbazide

2 g of 1- (2-carbomethoxybenzoyl) -2-methyl-4- (3-fluorophen-5184,120-yl) -3-thiosemicarbazide are dissolved in 100 ml of ethanol. The solution was cooled below 10 ° and 1.1 g of sodium borohydride was added. After stirring at room temperature for 60 hours, water was added to select an amorphous precipitate. The precipitate was collected and dilute hydrochloric acid was added to the filtrate to adjust the pH to 7. A further precipitate formed and was collected by filtration. The filtrate is then acidified to give the title product as a solid.

By the methods described in the previous examples, a large number of additional compounds of formula I are prepared. These compounds, as well as the compounds 1-12. Examples 1 to 6 are summarized in Table I, in which, in addition to the number of the compound, the values of the substituents R, m, R ² , R ³ , R ⁴ and Ar, as well as the melting point values, are shown.

Table I Compounds of formula I and their physical constants

Serial number of compound R m R ² R ³ R ⁴ Price Op.C ° 597 • COOCHj 0 - -ch ₃ H phenyl 153.5-154o 1685 -cooch ₃ - -CHfCH,) H phenyl 145-147 1686 --COOCH, - H H phenyl 140-142 2005 COOH - -ch ₃ H phenyl 155-156 2008 COOH 55 - H H phenyl 149-151 2044 -COONa r> - -ch ₃ H phenyl High melting point solid 2047 -coonh ₄ 55 - -ch ₃ H phenyl 165-166 2322 -COOCHj - CH, H benzyl 144-146 2324 -cooch ₃ H -Η benzyl 133-135 2325 -cooch ₃ - ~ ^CH 3 -Η 4-methylphenyl 138-140 2341 -COONa » - H -Η benzyl high melting point solid 2342 -coonh ₄ jj - H H benzyl 173-175 2370 -cooch ₂ ch ₂ ch ₃ » - -ch ₃ H phenyl 117-119 2371 ^ -COOCHjCf - -ch ₃ H phenyl 142-145 2372 -COO (CH ₂ ) ₃ CH ₃ - -ch ₃ H phenyl 98-100 2388 -cooch ₃ - CH, H 3-chloro-4-methylphenyl 142-146 2389 -cooch ₃ - ^CH 3 H 3-methylphenyl 138-140 2390 -cooch ₃ » - • ^CIÍ 3 H 3-methoxyphenyl 142-144 2391 -COOCHj - -ch ₃ H 2-fluorophenyl 152-154 2392 --COOCH, » - -ch ₃ H 4-fluoro-2-methylphenyl 127-129 2414 -COOC ^ CHjCl - CH, H phenyl 126-131 2415 -COO (CH ₂ ) ₆ Cl - 'CH H phenyl oil 2418 COOH - benzyl H phenyl 140-142 2422 -cooch ₃ 55 - benzyl H phenyl 103-106 2432 COOH 1 3-CH -ch ₃ H phenyl 123-126 2433 COOH » 3-CH H H phenyl 122-123 2434 -C00NH ₄ » 3-CH ₃ CH, H phenyl 154-157 2444 -C00 (CH ₂ ) ₄ CH ₃ CH, -COOCH, CH ₂ CHCH, 0 -ch ₃ H phenyl 131-133 2445 w - -ch ₃ H phenyl 126-129 2446 -COO (CH ₂ ) _s CH ₃ - -ch ₃ H phenyl 113-117 2450 COOH 1 6-NO ₂ - ^Title 3 -E phenyl] 160-163 2470 -conh ₂ 0 - - ^Cii 3 H phenyl 161-163 2472 -CON (CH.), 55 - CH, H phenyl 140-143 2474 COOH - -ch ₃ H 4-chlorophenyl 165-166 2479 COOH n -ch ₃ H benzyl 161-163 2480 COOH 55 - h H benzyl 183-184 2481 COOH 55 - CH. H 4-methylphenyl 156-158 2482 COOH » - CH. H 3-methylphenyl 133-135 2483 COOH 55 - -ch ₃ H 2-fluorophenyl 137-139

-6184 120

I. Bowl Base (Continued)

R m R ² R ³ R ⁴ Price M.p. COOH 0 _ ' ^CH 3 H 4-fluoro-2-methylphenyl 158-161 COOH n - -ch ₃ H 4-fluorophenyl 167-168 COOH ^CH 3 H 3-fluorophenyl 165-166 -cooch ₃ * - • ^CH 3 H 2-chlorophenyl 151-153 -cooch ₃ n - CH H 2-nitrophenyl 171-173 -cooch ₃ - -ch ₃ H 4-fluorophenyl 149-151 -cooch ₃ - -ch ₃ H 3-fluorophenyl 146-148 -COOCHj - -ch ₃ H 4-chlorophenyl 159-161 -cooch ₃ 5 » - • ^Title 3 H 3-chlorophenyl 143-145 -cooch ₃ the - ^CH 3 H 4-nitrophenyl 195 - 197 -cooch ₃ - -ch ₃ H 3- (trifluoromethyl -phenyl) 141-143 COOCH 3 > 9 - H H 3-methoxyphenyl 132-134 -cooch ₃ Ji - H H 3-chloro-4-methylphenyl 155-158 -COOCHj J » - H H 2-nitrophenyl 144-146 -COOCHg - H H 3-methylphenyl 138-140 -cooch ₃ - H H 2-chlorophenyl 149-151 -cooch ₃ » - -ch ₃ H 2-naphthyl 135-137 -cooch ₃ - H H 2-fluorophenyl 151-153 -COOCHj » - H H 4-fluorophenyl 163-165 -cooch ₃ - H H 4-methylphenyl 151-153 -cooch ₃ » H H 3-fluorophenyl 158-160 -cooch ₃ n - H H 4-chlorophenyl 162-164 -cooch ₃ - H H 3-chlorophenyl 153-155 -cooch ₃ - H H 3- (trifluoromethyl) - phenyl 161-163 -COOCH ₃ » - H H 1-naphthyl 146-148 -cooch ₃ - H H 2-naphthyl 148-150 COOH 99 - ^CH 3 H 3-chlorophenyl 157-158 COOH 9T - ^CH 3 H 4-nitrophenyl 200 COOH » - -ch ₃ H 1-naphthyl 159-160 COOH » ^CH 3 H 2-naphthyl 112-114 COOH » - -ch ₃ H 3 <trifluoro-methyl) - phenyl COOH - H H 3-methoxyphenyl 150-152 COOH » - H H 3-chloro-4-methylphenyl 178-183 COOH H H 2-nitrophenyl 170-171 COOH » - H H 3-methylphenyl 169-170 COOH 91 - H H 2-chlorophenyl 165-167 -COOfCH,) ,, CH, 39 - -ch ₃ H phenyl oil -COO (CH _i ) ₁₀ CH ₃ - -ch ₃ H phenyl oil -COOiCHj ^ CH, -cooch ₂ ch ₂ -o- - -ch ₃ H phenyl oil -CHjCHj » - -ch ₃ H phenyl oil -COOC ^ CH-ICHjXCH / '-COOCH, CH-O- - -ch ₃ H phenyl oil - <αι ₂ ) ₃ αν -cooc ₂ h ₄ -oc ₂ h ₄ - - -ch ₃ H phenyl oil -0-c ₄ h ₉ - CH H phenyl oil -COOCH ₂ -C- (CH ₃ ) ₃ - -ch ₃ H phenyl oil COOH » · " -ch ₂ ch = ch ₂ H phenyl 105-125

-715

Table I (continued)

Serial number of compound R m R ² R ³ R ⁴ Price Op.C ° 2668 COOC ₂ H ₄ OC ₂ H ₄ -, -OC ₂ H _s 0 -ch ₃ H phenyl oil 2669 -COOCH ₂ CH ₂ -phenyl - ^CH 3 H phenyl 131-133 2697 COOH - H H 2-naphthyl 171-174 2698 COOH - H H 1-naphthyl 158-159 2699 COOH - H H 3-trifluoromethyl) phenyl 167-170 2700 COOH - H H 4-nitrophenyl 298-302 2701 COOH - H H 3-chlorophenyl 169-170 2702 COOH - H H 4-chlorophenyl 187-189 2704 COOH Ji - H H 3-fluorophenyl 167-168 2705 COOH »> - H H 4-methylphenyl 164-166 2707 COOH 5 » - H H 4-fluorophenyl 179-181 2708 COOH Ji - H H 2-fluorophenyl 170-171 2721 COOH 2 - - ^CH 3 H 3,4-dichlorophenyl 165-166 2722 COOH 0 - - ^CH 3 H 4-methoxyphenyl 168-170 2723 COOH - -ch ₃ H 2-methylphenyl 173-180 2724 COOH CH H 4-bromophenyl 175-176 2725 COOH - H H 3,4-dichlorophenyl 178-179 2726 COOH » - H H 4-methoxyphenyl 198-201 2727 COOH » - H H 2-methylphenyl 179-180 2728 COOH » - H H 4-bromophenyl 178-181 2729 -COO (CH ₂ ) _u -CH ₃ * - H H phenyl solid material 2732 -COO (CH ₂ ) ₁₀ -CH ₃ - H H 3-fluorophenyl solid material 2733 -COO (CH ₂ ) _IS CH ₃ - H H phenyl solid material 2734 -C00 (CH 2) ₁₄ CH ₃ - -ch ₃ H 3-fluorophenyl oil 2735 -COO (CH _{2) 3} CH _1s - -ch ₃ H 4-fluorophenyl solid material 2736 -COO (CH,), "CH, » - -ch ₃ H 4-chlorophenyl solid material 2740 -CO0C, H, -0-C ₄ H _a - - ^CH 3 H 3-fluorophenyl solid material 2741 -COOC ₂ H ₄ -OC ₄ H _? - - ^CH 3 -J 4-fluorophenyl solid material 2742 -cooc ₂ h ₄ -oc ₄ h ₉ » - CH, H 4-chlorophenyl solid material 2743 -C00 (CH ₂ ) ₉ CH ₃ » - -ch ₃ H phenyl oil 2744 -COOCCHJ ^ CH - -ch ₃ H phenyl tire 2745 -COOCH ₂ CH ₂ -Br - - ^Title 3 H phenyl tire 2746 -COO (CH ₂ ) ₇ CH ₃ » - H H phenyl 117-121 2749 -COO (CH ₂ ) ₉ CH ₃ - H H phenyl 103-105 2750 -COOCH CH, - H H phenyl 148-150 2753 COOH 1 5-CH -ch ₃ H phenyl 131-132 2754 COOH 5-CH H H phenyl 137-139 2756 --COOCH, » 6-NO ₂ -ch ₃ H phenyl 130-135 2760 --COOCH, 5-CH ₃ H H phenyl 111 - 113 2762 -coonh ₄ 5-CH H H phenyl 170-172 2771 -coonh ₄ n 6-CH ₃ CH, H phenyl 102 (0) 2772 COOH 5-NO ₂ -ch ₃ H phenyl 123-124 2777 COOC ₂ H ₄ OC ₂ H ₄ - - ⁰ c ₂ H ₅ D H H phenyl 119-124 2778 -COOCH, CH, -phenyl » - H H phenyl solid material 2779 COOC ₂ H ₄ OC ₂ H ₄ - -OC.H, 0 H H phenyl solid material 2781 -COOC ₂ H ₄ -O-CH ₃ - H H phenyl solid material 2783 -COOC ₃ H ₆ -Br » - H H phenyl 72-75 2784 COOH 1 3-F ch, H phenyl 134-136 2787 COOH » 3-F H H phenyl 149-150 2788 COOH 0 - -ch ₂ ch ₃ H phenyl 153-155 2790 -COOH, pyridine salt » -ch ₃ H phenyl 126-129

-8184 120

Table I (continued)

R m R ² R ³ R ⁴ Price M.p. COOH 0 _ H CH, phenyl 168 -cooch ₃ 99 - H CH, phenyl 95-99 --COOCH, - • ^CH 3 CH, phenyl 105-106 -cooch ₃ - H H 3,4-dichlorophenyl 155-157 -cooch ₃ - H H 4-methoxyphenyl 149-151 -cooch ₃ 99 - H H 2-methylphenyl 175-177 -cooch ₃ 99 - H H 4-bromophenyl 163-165 -cooch ₃ - CH, H 4-methoxyphenyl 126-128 COOH 1 5-chloro CH, H phenyl 125-127 COOH 5-chloro H H phenyl 280-283 -cooch ₃ -COOH, triethylene- 0 - ^C A H phenyl 166-168 diamine salt - CH, H phenyl 189-190 -COO 99 - CH, H phenyl 181-183 COOH 2 4,5-dichloro CH, H phenyl 320 - 323 COOH 99 4,5-dichloro h H phenyl 158-159 -C00NH ₄ 99 4,5-dichloro h H phenyl 170 (decomposes) -coonh ₄ 4,5-dichloro • ^CH 3 H phenyl 112-115 -COOLi 0 - ^CH 3 H phenyl - COOH 1 3-Br CH H phenyl tire -coonh ₄ 6-F CH, H phenyl 163-165 -coonh, » 6-F h H phenyl 180 (decomposes) COOH 2 3,6-dichloro - ^CH 3 H phenyl 116-117 -cooch ₃ -COOH, dimethyl- 0 - CH, H 2,4-dimethylphenyl 155-157 morpholinium salt -COOH, 4H-pyrido [1,2-d] - pyrazine - ^CH 3 H phenyl 137-139 salt -COOH, diethylamine- 99 - ^CH 3 H phenyl 168-170 salt 19 - CH, H phenyl 147-149 COOH - CH, H 2,4-dimethylphenyl 172-178 -C00NH ₄ l 5-Nitro - ^addresses H phenyl 144-145 COOH 0 - CH, CH, phenyl oil COOH l 6-CF CH, H phenyl 68-74 COOH 0 - phenyl H phenyl 151 (decomposes) COOH 1 4-nitro -ch ₃ CH, phenyl 83-90 -COOCR, 0 - CH, H 2-carbethoxy-phenyl 120-122 -COOCHj - CH, H 4-phenoxyphenyl 163-165 --COOCH, 99 CH, H 4-butyl-phenyl 143-145 -cooch ₃ - CH, H 3- (methylthio) phenyl 97-99 --COOCH, - CH, H 4-benzyloxyphenyl 162-164 -cooch ₃ - 'CH, H 4- (dimethylamino) - phenyl 138-140 -COOCHj ff - CH, H 4-methylbenzyl 147-149 --COOCH, - CH, H 2,6-dichlorophenyl 162-164 -cooch ₃ - - ^CH 3 H 4-carbethoxy-phenyl 142-144 -cooch ₃ 99 - CH, H 4-isopropylphenyl 156-158 COOH CH, H 2-carbethoxy-phenyl 158-159 COOH 99 - CH, H 4-phenoxyphenyl 140-142 COOH 99 - CH, Ή 4-butyl-phenyl 134-135 COOH 99 - CH, H 3- (methylthio) phenyl glassy solid

-919

Table I (continued)

Serial number of compound R m R ² R ³ R ⁴ Price M.p. 3022 COOH 0 CH H 4-isopropylphenyl 116-118 3023 COOH -ch ₃ H 4-benzyloxyphenyl 138-139 3024 COOH -ch ₃ H 4- (dimethylamino) - 3025 COOH the CH, H phenyl 4-methylbenzyl 163 - 165 157-158 3026 COOH n CH, H 4-carbethoxy-phenyl 160-161 3027 COOH 99 CH, H 2,6-dichlorophenyl 156-157 3108 -COO » CH, H 3-fluorophenyl 184-185 3109 -coonh ₄ CH, H 3-fluorophenyl 155-157 3116 COOH, » CH, H phenyl oil 3137 -CO-l-piperidinyl CH, H phenyl 150-152 3146 -COOH, octylamine salt 99 CH, H phenyl 133-135 3147 COOH 99 - -ΟΗ, αξΟΗ H phenyl 155-157 3151 COOH 99 CH, H 2,3-dimethylphenyl 118-120 3152 COOH 99 CH, H 2,4,5-trimethylphenyl 1.60 (rearranged) 3153 COOH 99 CH, H 2,5-dimethylphenyl 130 (rearranging) 3158 COOH 99 CH, H 3,5-dimethylphenyl 107-110 3159 COOH 99 CH, H 3-ethylphenyl not cleaned 3160 COOH 99 CH, H 3,4-dimethylphenyl 126-128 3180 -COOH, a salt with benzyldimethylamine 99 CH H phenyl 68-85 3181 -COOH, a salt with phenyldimethylamine CH, H phenyl 145-147 3182 -COOH, (2,3-dihydroxypropyl) -dimethyl · amine salt 99 CH, H phenyl (Dec) 139-141 3183 -COOH, a salt with trioctylamine 99 CH, H phenyl (Dec) oil 3184 --COOCH, 99 -C ^ CHjOH H phenyl 147-149 3185 --COOCH, CH, H 2,3-dimethylphenyl 136-138 3186 -cooch ₃ » CH, H 2,4,5-trimethylphenyl 150-152 3187 --COOCH, 99 CH, H 2,5-dimethylphenyl 146-147 3194 -cooch ₃ 99 CH, H 3,4-dimethylphenyl 142-144 3195 -cooch ₃ 99 CH, H 3,5-dimethylphenyl 153-155 3196 -cooch ₃ 99 CH, H 3-ethylphenyl 78-81 3210 COOH, tetrahydro-furan -adduktum 99 CH, H phenyl 155-158 3284 -CONH (CH ₃ ) ₃ » CH, H phenyl 141-142 3285 -conhch ₂ ch ₂ ch, » CH, H phenyl 144-148 3290 -CONHCH-CH, CH, CH, H phenyl not cleaned 3349 ^CH 3 -cooch ₃ 99 CH, H 4-bromophenyl 156-159 3350 -cooch ₃ 99 CH, H 3-nitrophenyl 178-180 3352 -cooch ₃ 99 CH, H 3,4-dichlorophenyl 159-161 3358 -COOCH-CH, 1 ³ 99 CH, H phenyl 115-117

ch ₃

-10184 120

Table I (continued)

Serial number of compound R m R ² R ³ R ⁴ Price M.p. 3577 -COO / ₂ Ca 0 ^CH 3 H phenyl > 300 3578 -COO / ₂ Zn > 5 - ^CH 3 H phenyl 170-175 (decomposes) 3579 -COO / ₂ Cu - - ^CH 3 H phenyl 150-153 (decomposes) 3580 -COO / ₃ Fe - • ^CH 3 H phenyl 152-157 (decomposes) 3581 -C00 / ₂ Mn - CH, H phenyl 158-160 (decomposes) 3582 -COO / ₂ Fe - • ^CH 3 H phenyl 160-180 (decomposes) 3676 COOH 2 4,5-dichloro H H phenyl 164 (decomposes) 3716 -ch ₂ oh 0 - ^CH 3 H 3-fluorophenyl 136-137 3873 -conh-ch ₂ ch ₂ - phenyl » ^CH 3 H phenyl 154-156 3874 -CONH-CH ₂ -4-fluorophenyl » - ^CH 3 H phenyl 156-158 3875 -CONH-benzyl n - ^CH 3 H phenyl 143-146 3876 CONH-nonylphenol - ^CH 3 H phenyl 151-152 3877 -CONH-CH ₂ (4-methoxyphenyl) -ch ₃ H phenyl 149-151 3879 CONH-cyclopropyl - -ch ₃ H phenyl 144-146 3880 -C0N (CH, CH, CH,) " - -ch ₃ H phenyl 132-134 3883 CH {2 5 -conh-ch ₂ chch ₂ ch ₂ ch ₂ ch ₃ - ^CH 3 H phenyl 143-145 3884 -CONH (CH ₂ ) CH ₃ - CH, H phenyl 145-147 3866 -CON-benzyl - CH, H phenyl 167-169 3869 isopropyl -CON-benzyl » - ^CH 3 H phenyl 132-134 3872 ethyl -CONHC (CH ₃ ) ₃ 2 3,6-dichloro CH, H phenyl 173-174 3974 -CONH (CH ₂ ) ₃ O- (CH ₂ ) ₂ OCH ₃ 0 - ^CH 3 H phenyl 140-142 3975 -CONH (CH ₂ ) ₃ O- (CH ₂ CH ₃ ), » __ -ch ₃ H phenyl 146-148

The term "plant growth regulator" is used to denote changes in the normal growth of a plant during its maturation period. Such changes include shortening or lengthening of the stem, flower growth or increase in fruit yield, reduction in plant shape, growth or density of branches, reduction in the number of buds, hindering the development of root shoots, fruit thinning, leaf thinning, increased resistance to cold, drought and other weather conditions, root growth and delay in ripening. 50 In addition, other changes known in the art may occur.

From the types of plant growth regulators shown above, the agents containing the active compounds of the formula I are mainly used to modify the further growth of plants. However, certain herbicidal effects may occur due to changes between plant species.

The plant growth regulators of the present invention are used in a variety of plant species. 60 12

Plant growth regulators are particularly valuable in controlling the growth of, for example, cereals, legumes, and many vegetable and fruit products. The plant growth controlling agents of the present invention can be used to control the growth of ornamental plants, houseplants and other plants to increase their decorative value.

Plant growth regulating agents containing the active compounds of formula (I) may be applied to all, part, or any viable member of the plant. Thus they can be applied, for example, to the leaves, trunk, flowers, fruits, roots, root stems, tubers, seeds of the plant.

The agents can also be applied to the soil to exert a regulatory effect on the sown seeds and on the already emerged and developing plants.

The amount of agent to be used is not critical if the agent is used at least in an amount effective to control plant growth. Generally, it is sufficient to apply between 0.7 g / ha and 11 kg / ha of active compound, the amount used to vary according to (I).

-11184 120 depending on the active ingredient, the plant species, their state of development, the nature of the desired growth control, and other factors known in the art. Smaller amounts of some of the active compounds of formula I can be used, such as those containing the active ingredient of 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide, preferably at or above 1.1 kg soybean. a lower amount of active ingredient per hectare is also sufficient. Advantageous growth control effects are obtained even when 0.35 g of active ingredient is applied per hectare and the optimal amount is about 1.1 kg / ha of active ingredient. In strawberry fields, the yield of strawberries can be increased by 1080 kg per hectare using the amount of 0.11 kg / ha of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide. When wild game trees are treated at 1000 ppm in spring with charcoal containing 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide (50:50 in kerosene vegetable oil), the reduction in flower volume, and achieving leaf multiplication.

When used for seed treatment such as Soy max (soybean), Hordeum vulgare (barley), Triticum aestivum (wheat), Oryza sativa (rice), Setaria italica (muhar) and Brassica napus (rapeseed), up to about 1% by weight of the core.

As shown below, single use already provides the desired plant growth control, but multiple treatments can be performed during the growth phase to achieve the best growth control possible.

Agents containing compounds of the formula I are preferably used in the Salt max plant. When such agents are applied to the max leaves of its salt, a large change in growth can be observed as early as 18 days after treatment, such as flower growth, seed weight growth, and at the same time, usually six plant buds. The best practice is to repeat the mail treatment several times every 15-20 days. The first treatment is carried out at the beginning of flowering, thus achieving the best possible effect. In soil treatment (including seed treatment) the growth regulating effect can be observed for 30 days and also a herbicidal effect.

In another preferred use of the compounds of the invention containing the active compounds of formula (I), they are applied to pod plants in order to increase the yield.

The results obtained in legumes and tomatoes show that the agents containing the active compounds of the formula I exhibit an outstanding combination of cytokinin and auxin activity. More Chlorophyll A is present in the treated plants as shown by the color change. Higher levels of photosynthesis occur, which is manifested in the increased weight of the treated plants, although the plants may be inferior. At the same time, the leaf and the fruit are growing enormously.

The active compounds of the formula I are generally used in the form of preparations. The formulations of the invention contain the active compounds of the formula I and excipients and / or excipients commonly used in agriculture. The excipient may be any substance which enhances the growth-regulating action of the compounds of formula (I). An excipient is, for example, a solvent, an inert diluent, a surfactant, a dispersant which aerosolizes the active ingredient.

Suitable inert diluents include powdered limestone, attapulgite chalk, kaolin chalk, montmorillonite chalk, diatomaceous earth and silicates. Suitable surfactants include sulfonated lignin, naphthalene sulfonates, alkylbenzene sulfonates, alkylphenols, fatty acids, fatty alcohols adducts with ethylene oxide and / or propylene oxide.

Wettable powder formulations are preferred for the solid active compounds of formula (I). Wettable powders are finely divided mixtures of the compounds of formula (I), an inert diluent and a surfactant. The inert carrier and the surfactant may be any of the above. Wettable powders are formulations which, when diluted with water, form a solution.

Emulsifiable concentrates are mixtures of a compound of formula (I), a water immiscible solvent and an emulsifier. Solvents include aromatic and aliphatic hydrocarbons and derivatives such as xylenes, various petroleum distillates and vegetable oils such as corn germ oil, soybean oil and cottonseed oil. The emulsifier may be one or more of the above-mentioned surfactants. The emulsifiable concentrates, when diluted with water, also provide ready-to-use solutions.

Compounds of formula (I) which are relatively water soluble may also be formulated as water soluble concentrates. They preferably contain, in addition to the active ingredient of the formula (I), a surfactant of the above type which facilitates the dissolution of the active ingredient when diluted in aqueous solutions ready for use.

The compositions may generally contain from 0.1 to 80% by weight of the active ingredient of the formula I and from 0.1 to 75% by weight of the surfactant. As mentioned above, the above preparations are prepared by dilution into ready-to-use solutions. For certain typical uses known in the art, these concentrated compositions may also be used directly in their form for treatment. Small volume rotary nebulizers known as "Micron Herbi Sprayer" are suitable for such applications.

The aqueous dispersions or emulsions preferably also contain moistened autumn. They delay the drying of the composition on the plants to which they have been applied. Suitable wetting agents include glycerol, diethylene glycol, solubilized lignin such as calcium lignin sulfonate. The formulations may also contain other active ingredients or additives. Examples of such additives are protective colloids, such as gelatin, glue, casein, rubber and poly (allyl alcohol), as well as sodium phosphate and cellulose ethers, stabilizers and adjuvants such as non-volatile oils.

The compounds of the formula I are active compounds 13

The effect of plant growth regulators containing -12184 120 is shown in the following examples.

aqueous solution of pH 5.93. The bulk density of the preparation is 0.35 g / cm ³ .

Example 13 5

120 g of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide, 400 ml of water and 173 g of polyoxyethylene (5) soyamine (Ethome S15) are combined. The mixture was stirred at ambient temperature for 10 hours, during which time a clear solution was obtained. Trimethyl nonyl polyethylene glycol ether (Tergitol TMN-10) (200 g) was then added with stirring. An additional 107 ml of water was then added to give the following composition:

active ingredient (see above) 12.0% w / w Polyoxyethylene / 5H-Siamine 17.3% w / w Trimethyl-nonyl polyethylene glycol ether 20.0% w / w 50.7% w / w

A sample of this preparation is subjected to a storage test.

The solution remains stable when stored at 15 to 20 ° C.

Example 14

A wettable powder is prepared by grinding 60 g of potassium dihydrogen phosphate in a shear mixer and drying the powder in an oven at 50 ° C overnight. Potassium dihydrogen phosphate was added with 7 g of 1- (2-carboxybenzoyl) -2-30-methyl-4-phenyl-3-thiosemicarbazide potassium salt, 5 g of (sodium naphthalene) formaldehyde condensate (Morwet D). -425) and 28 g of Atwet W-13 (product containing 50% polyethoxylated fatty acid ester embedded in an equal weight of water soluble organic material). These components are mixed thoroughly. The wettable composition contains the following ingredients by weight:

active ingredient (see above) 7% by weight potassium dihydrogen phosphate 60% by weight (sodium naphthalene) formaldehyde condensate (dispersant) 5% by weight

Atwet W-13 (50% Nonionic Embedded Surfactant) 28%

Example 15

A water - soluble composition is prepared having the following composition by weight:

- (2-Carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide ammonium salt 25% (naphthalene) formaldehyde

-condensate (dispersant) 5% by weight

Atwet W-13 (50% Nonionic Embedded Surfactant) 70%

The product is a white powder mixture. 60 of this mixture

Example 16

A wettable powder containing an increased amount of the active ingredient is prepared by adding 150 g of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide, 30 g of Georgia attapulgite chalk, 10 g of sodium diisopropylnaphthalene. sulfonate (Morwet IP) and 10 g (sodium naphthalene) formaldehyde condensate (Morwet D-425) are thoroughly mixed. The mixture is milled in a mill and the average particle size is determined. The average particle size is 5 microns. The resulting composition is as follows:

active ingredient (see above) 75s% Georgia attapulgit chalk 15s% sodium diisopropyl naphthalene sulphonate (wetting agent) 5s% (sodium naphthalene) formaldehyde condensate (dispersant) 5s%

Example 17

A suitable wettable powder formulation is obtained when 0.32 kg of precipitated silica (Hi-Sill 233), 0.36 kg of trinethyl nonyl poly (ethylene glycol) ether (Tergitol TMN-10), 0.18 kg of l- (2-Carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide and 0.036 kg (sodium naphthalene) formaldehyde condensate (Morwet D-425) are mixed and the mixture is ground, where the latter serves as a dispersant. The resulting composition is as follows:

active ingredient (see above) 20% by weight of precipitated silica 36% by weight of trimethyl-nonyl poly (ethylene glycol) ether 40% by weight (sodium naphthalene) formaldehyde condensate 44% by weight

The above composition has a bulk density of 0.145 g / cm ³ , an average particle size of 10.4 microns and a wetting time of 49 seconds.

Example 18

A water-soluble dispersion of the active ingredient was prepared by adding 0.28 kg of 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide, 0.56 kg of sorbitan monooleate ethoxylate, Tween 80 and 0. 37 kg of tetrahydrofurfuryl alcohol are mixed. When the composition is diluted with water for spraying, microcrystals of the active compounds formed are uniformly suspended in the surfactant.

-13184 120

Example 19 A plant growth controlling emulsifiable concentrate containing the active ingredient of formula (I) is prepared by dissolving the active ingredient and the wetting agent in a vegetable oil or aromatic hydrocarbon solvent. The composition of an emulsifiable concentrate is as follows:

1- (2 - [(2-ethylhexyloxy / carbonyl] benzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide 12% by weight dialkyl phenoxy polyethoxylated ethanol (Igepal DM-530) 12% by weight corn germ oil 76 s%

Example 20 A plant-soluble water-soluble powder containing a compound of formula (I) is prepared by mixing a salt-form active ingredient with a solid anionic surfactant such as Naxonate KX (potassium xylene sulfonate) or Naxonate KT (potassium toluene sulfonate). When diluted, a compatible inorganic salt may be added. The composition of such a water-soluble powder is as follows:

Potassium salt of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide 6.2% by weight Potassium carbonate 50.0% by weight

Naxonate KX (potassium xylene sulfonate) 43.8% by weight

A solid nonionic surfactant such as Myq 53 (polyoxyethylene / 50 / stearate) may also be used.

Example 21

Another water-soluble powder is prepared in the conventional manner and has the following composition by weight:

Potassium salt of 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide 6.2%

Morwet D-425 / (sodium naphthalene) formaldehyde condensate) 5.0% by weight

Macol SA-40 [poly (oxyethylene (4 / lauryl alcohol)) 44.4% sorbitol 44.4%

Example 22

A further emulsifiable concentrate may be prepared by mixing the salt form of the active ingredient with suitable additives. The concentrate obtained has the following composition:

1- (2-Carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide 4.5% by weight

1.5 s% of 2,6-lutidine

Atlox 3459F (anionic-nonionic mixture of dodecylbenzene sulfonate calcium and polyethoxylated fatty acid esters) 10.0% by weight cyclohexanone 84% by weight

Example 23

The use of the plant growth regulators and herbicides according to the invention for controlling plant growth and controlling unwanted plants can be easily demonstrated in a greenhouse experiment according to the following methods.

Pre-emergence application

6.4 cm deep plastic bowls were filled with soil and the soil sprayed with the compositions of the present invention in an amount sufficient to provide 5.5 kg of active ingredient per hectare. Seeds of 6 plant species are then planted into the soil and the seeds are covered with 0.6 cm thick soil. The spray liquid is prepared by dissolving a sufficient amount of the active ingredient in 15 mL of acetone and adding 4 mL of a solvent emulsifier mixture of 60 wt% polyethoxylated vegetable oil emulsifier (96 wt% active ingredient, Emulphor EL-719), 20 wt% deodorized kerosene and 20% w / v, the total volume is then adjusted to 60 ml by addition of warm water. Twenty-one days after sowing and treatment, the plants are examined and the results are given in the following scale.

Abbreviation in the table of ^effects

Effect on growth F

Epinasty E

Growth Reduction G

Destruction N

K did not come out

Impact level = no effect = weak effect, temporary effect = moderate effect = strong effect = maximum effect

In some cases, more than one effect is investigated and results are recorded for groups of plant species.

Post-emergence application

Different varieties of plants were grown in polystyrene foam bowls and Lycopersicum esculentum individual plants were grown in ten centimeter bowls15

-14184 120 bans. An aqueous spray is prepared from the agents of the present invention and sprayed at a rate of 600 liters / ha on the plants, corresponding to an amount of 5.5 kg / ha of active ingredient. for comparison, a mixture of 600 liters / ha is sprayed onto other plants that do not contain the active ingredient glaze. The evaluation is carried out according to the scale given above.

The results obtained for pre-emergence and post-emergence experiments are shown in the table below.

(Table II).

II. Spreadsheet

Effect on vegetation

Pre-emergence effect

Post-emergence effect

The compound

number Digitaria sanguinalis Celosia plumosa bromus inermis Setaria italica Raphanus sativus beta vulgar Setaria italica Medicago sativa Avena sativa Raphanus sativus beta vulgar '2 5 a> c o, g 83 * i — 1 <u 597 K4 F2G1 K3G3 F3G3 F3G2 F3G2 N1G1 F3 F2 G1F1 F2G1 F3 1685 K4 F3G3 F3G3 F3G2 F1G1 F3G3 0 0 0 0 F2 N1F1 1686 0 RIP F2 0 0 F2 cl RIP 0 NI F2G1 N1F1 2005 K4 F3G2 K4 F3G3 G3 K4 0 F2G1 G1 G2F1 F3G1 F2 2008 0 K2 RIP 0 K2 WHO 0 F2G2 N1G1 F2G1 F2G1 0 2044 K4 F1G1 F3G3 F2G2 F1G2 K4 F2G1 F3G1 F2 N1G1 F2G1 F2G3 2047 F3G2 RIP F2G1 F2G1 RIP F2 F2G1 F2G2 F1G1 F2G1 F2G2 F2G2 2322 NI N3G2 G1 0 0 N3G3 0 0 0 0 RIP 0 2324 N1G2 0 0 0 0 WHO 0 0 0 0 RIP 0 2325 N3G3 N3G2 N3G3 N2G3 G3 K3G2 N1F1 F2 RIP F1G1 F1G1 F3 2341 F2G1 RIP F2 F3G2 G1 F2G1 RIP RIP 0 F1G1 F1G1 0 2342 RIP 0 F2 F2 0 F2 0 RIP 0 F2G1 F1G2 RIP 2370 K4 K4 K4 F3G3 F3G2 F3G3 F2G1 N1G3 N1G1 N1F1 F1G3 F3 2371 K4 K4 F3G3 F3G3 F3G2 F3G3 N1G1 F3G3 F1G1 F2G2 F1G2 F3G3 2372 K4 F3G3 F3G3 F3G3 F3G3 F3G3 N1G2 N1G3 NI N1G2 F3G2 F3 2388 F2G2 F1G1 F3G1 F3G2 F3G2 F3G1 0 F3G1 RIP F2 F3G1 F3 2389 K4 K4 K3F1 F3G3 F3G3 K4 F2 F3G3 F2 F2 F3G3 F3 2390 K3G3 F3G2 F3G1 F3G3 F3G2 F3G2 THE F3G2 RIP RIP F2G1 F3 2391 K4 K4 K3F1 F3G3 F3G3 F3G3 F2 F3G2 F2G2 RIP F3G1 F3 2392 F3G3 F3G3 F3G1 F3G2 F2G1 F3G1 0 RIP 0 0 F2 F2 2414 K4 F3G3 F3G3 F3G3 F3G3 F3G3 F2 F3G3 F2 RIP F3G1 F3 2415 K4 F3G3 K4 F3G3 F3G2 F3G3 F2 F3G3 RIP 0 F3G1 F3 2418 F1G1 K2 F2G1 0 0 F2G1 0 RIP 0 0 F2 F2 2422 0 0 F2 0 0 0 - - - - - 2432 K4 F3G3 F3G3 F3G3 F2G1 F3G3 F2 F3G2 RIP F2 F3G1 F2 2433 F3G2 F3G3 F2G1 F2G1 F3G2 F1G1 RIP F3G2 RIP RIP F3G2 F3 2434 F3G3 F3G3 F3G1 F2G1 F3G1 F3G1 RIP F3G2 F2 RIP F2G1 F3 2444 K4 K2G1 F3G1 F3G2 F1G2 F2G2 N2G2 - - F2 N2G1 F3 2445 F3G3 K2G1 F3G1 F3G2 F1G1 F2G2 0 F2 0 0 F2G1 F2 2446 K4 K4 F3G3 F3G3 F2G2 F3G2 - F2G1 0 RIP F1G2 RIP 2450 F2G2 K4 F2 F3G2 F2G2 F3G2 N1G1 F2G1 0 RIP F2 RIP 2470 K4 K4 F3G3 F3G3 F3G2 0 NI F2 0 RIP F2G2 F2G2 2472 F3G3 K4 F3G2 F3G3 F1G1 F2G2 0 F2G1 0 N1F1 F2G1 F2G2 2474 K4 K4 F3G3 F3G3 F3G2 F3G2 NI N1G2 0 N1G1 F2G2 F3 2479 0 0 RIP RIP 0 0 N1G2 RIP NI RIP F1G1 0 2480 0 0 0 0 0 0 - - - - - - 2481 K4 K4 F3G3 F3G3 F3G2 F3G2 N1G2 N3G3 G1 F2G1 N4 F2G1 2482 K4 K4 F3G3 F3G3 F3G2 K4 N1G2 F2G1 F1G1 F2G1 F2G2 F2G1 2483 F3G3 K4 F3G3 F3G2 F3G1 F3G2 N3G3 F2G3 G1 F2G1 F2G1 F3 2484 16 F3G2 F3G3 F3G2 F3G2 F2G1 F3G2 N2G1 RIP G1 F1G1 F2G2 RIP

-15184 120

32

II. Table (continued)

Effect on vegetation

Pre-emergence effect Post-emergence effect

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2487 K4 F3G2 F3G3 F3G3 F3G3 F3G3 N1G1 - NI F2G2 F2G1 F2 2488 F3G3 F3G2 F3G3 F3G3 F3G2 F3G2 N1G2 F2G2 F1G1 N1F1 F2G1 F3G2 2563 F2G2 F2G1 F3G1 F3G2 F2G1 F2G1 N3G3 RIP 0 0 F2G1 F3E2 2564 F1G1 F1G1 F3G1 F3G2 F1G1 F1G1 N1G1 0 0 0 RIP F3E2 2567 K4 F3G2 F3G3 F3G3 F3G2 F3G3 N4 F3G2 RIP F2 F3G2 F3G3 2568 F3G3 F3G3 F3G3 F3G3 F3G2 F3G3 N1G2 F3G2 F2 F2 F3G1 F3E3 2569 K4 F3G3 F3G3 F3G3 F3G3 F3G3 F2G2 F3G2 RIP F2G1 F3G2 F3G2 2570 F3G3 F3G3 F3G2 F3G2 F3G2 F3G3 F2G2 F3G2 RIP F2 F3G2 F3G2 2571 F2G2 F2G1 F3G1 F3G2 F2G1 F1G1 F1G1 F2 0 RIP F2 F3E2 2572 F2G1 F2G1 RIP F2G1 F1G1 RIP RIP F2 0 F2G1 F3G2 F3G2 2573 RIP RIP F2 RIP 0 0 0 RIP 0 0 RIP RIP 2574 RIP RIP F2 0 0 0 0 RIP 0 0 F2 RIP 2576 0 0 0 0 0 0 - - - - 2577 F1G1 F1G1 F2 F2G1 RIP RIP NI RIP 0 0 F2 0 2578 RIP RIP F2 RIP 0 0 0 RIP 0 0 F2 RIP 2579 K4 F3G3 F3G3 F3G3 F3G2 F3G1 F2G1 F3G3 RIP F2G1 F3G2 F3E2 2580 0 0 RIP 0 0 0 0 RIP 0 RIP F2 0 2581 F2G1 0 RIP 0 0 0 0 RIP 0 0 RIP 0 2583 F1G1 RIP F2 RIP 0 RIP 0 F3C1 RIP RIP F3C1 RIP 2584 RIP RIP F2 RIP 0 0 0 F3G3 RIP F1G1 F2G1 F1E1 2585 F3G3 F3G2 F3G3 F3G3 RIP F3G1 RIP F3E2 RIP F1G1 F3G1 F3E2 2586 RIP RIP F2 RIP 0 0 0 F3G2 0 F2G1 F3G1 F1E1 2588 RIP 0 RIP 0 0 0 0 0 0 RIP RIP 0 2589 0 0 0 0 0 0 0 0 0 RIP RIP 0 2590 0 0 RIP RIP 0 0 RIP F3G2 RIP F2 F3G1 F1E1 2591 K4 K3G3 K3G2 F3G3 F3G2 F3G1 F3G3 F3G3 F1G1 F3G1 F3G3 F3G3 2592 F3G3 F3G3 F3G3 F3G3 F3G2 F2G1 F3G2 F3G1 RIP F2G1 F2G1 F3G3 2594 F3G3 F3G2 K4 F3G3 F3G1 F2G1 N4 F3G3 G1 F2G1 F3G1 F3G1 2595 F2G2 F1G1 F3G1 F2G1 G1 F2G1 N1G3 F3G3 F1G1 F1G1 F3G1 F3E3 2597 F1G1 F2G1 F3 F2G1 F1G1 F2G1 G3F2 F3G2 RIP F2G1 F3G2 F3G3 2598 0 0 RIP 0 0 0 F1G1 F3G1 RIP F2G1 F3G1 F2E2 2599 RIP F2 F2 0 0 0 0 F3G1 0 RIP F2 F2E1 1603 0 0 0 0 0 0 0 RIP 0 F1G1 0 F1E1 2604 F2 F1G1 F3G1 F3G2 0 RIP 0 F2 RIP F2G1 F2G1 F2E2 2605 F3G1 F2G1 F2 F1G1 0 RIP 0 F2G1 0 F2G1 F2G1 F2E1 2622 F3G3 F3G2 K4 F3G3 F3G2 F3G2 N3G3 F3G2 RIP F2G1 F3G2 F3E3 2627 K4 F3G3 F3G3 F3G3 F3G2 F3G3 F2G2 F3G2 F1G1 F3G3 F3G3 F3E3 2628 F3G3 F2G1 F3G3 F3G3 F3G2 F3G3 F2G2 F3G2 RIP F1G1 F3G2 F3E3 2633 K4 F3G3 K4 F3G3 F3G2 F3G3 F3G3 F3G2 F2G1 F2G1 F3G2 F3E3 2634 F3G3 F3G2 F3G3 F3G3 F3G2 F3G3 F1G1 F3G2 RIP RIP F2 F3E2 2635 F3G2 F3G2 F3G3 F3G3 F2G2 F3G2 F1G1 F3G2 RIP F1G1 F2G1 F3E3 2636 F3G3 F3G2 F3G3 F3G2 F2G2 F2G2 F2G3 F3G2 RIP F1G1 F3G2 F3E3 2637 K4 F3G2 K4 F3G3 F3G2 F3G3 F3G3 F3G3 F1G1 F2G1 F3G2 F3E3 2641 F2G1 F2G2 F2G1 F3G2 F1G1 F2G1 F3G3 F3G3 RIP F1G1 F3G2 F3G1 2668 K4 F3G3 K4 F3G3 F3G1 F3G3 G2F2 F3G2 F1G1 F2G1 F3G3 F3G3 2669 F3G3 F3G2 K4 F3G3 F3G2 F3G3 F2G2 F3G2 F2G1 F2G1 F3G2 F3E3 2697 F2G3 F1G1 F3G1 F2G1 RIP F1G1 F2G1 F3G3 F2G1 F3G1 F3G1 F3E2

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34

II. Table (continued)

Effect on vegetation

Pre-emergence effect Post-emergence effect

Serial number of compound Digitaria saguinalis 1 ! Celosia plumosa bromus inermis Setaria italica ! Raphanus sativus beta vulgar Setaria italica Medicago sativa 1 1 ^! Avena sativa Raphanus sativus beta vulgar Lycopersicv esculentum 2698 RIP 0 0 0 0 0 RIP RIP RIP F1G1 F2G1 RIP 2699 RIP F1G1 RIP 0 0 0 RIP F1G1 0 F2G1 F2G1 F3E1 2700 0 0 0 0 0 0 RIP RIP 0 RIP F2 F3E1 2701 F2G1 F1G1 F3G1 RIP G1 0 F2G1 F3G2 RIP F2G1 F3G1 F3E2 2702 F3G1 RIP F3 F3G1 RIP F2G1 F2G1 F3G2 0 F2G1 F3G1 F2 2704 F2G1 F1G1 F3G1 F1G1 0 RIP RIP F3G1 RIP F3G1 F2G1 F3E1 2705 RIP F1G1 F2 RIP 0 RIP F2G1 F3G2 F2 F2G1 F3G1 F2 2707 RIP 0 0 0 0 0 RIP F2 RIP F2G2 F3G1 RIP 2708 0 0 0 0 0 0 RIP RIP 0 RIP F2 F2E1 2721 F3G3 F2G2 F3G2 F3G2 F3G2 F3G3 F2G2 F3G3 F2G1 F3G1 F3G2 F3G3 2722 K4 F2G2 F3G3 F3G2 F3G3 F3G3 F2G1 F3G2 RIP F3G1 F3G1 F3E3 2723 F3G3 F2G2 F3G2 F3G2 F3G2 F3G2 F2G1 F2 RIP 0 F3 F3E2 2724 K4 F3G3 K4 F3G3 F3G3 K4 F2G2 F3G2 F1G1 F2G1 F3G2 F3E3 2725 F3G2 F2G1 F3G1 F3G1 F1G1 F2G2 RIP F3G1 0 F2 F3G1 F3E2 2726 F3G2 RIP F2 F2G1 F1G1 F2G1 RIP F3G1 RIP RIP F2 F2E1 2727 F1G1 RIP F2 F2G1 0 0 RIP F2G1 0 RIP F2 F2 2728 F3G2 F2G2 F2G2 F3G1 F1G1 F1G1 F1G1 F3G3 F2G1 F2G1 F2G1 F3E1 2729 F1G1 F2G2 RIP 0 0 0 RIP F2 0 0 RIP RIP 2732 RIP 0 RIP F1G1 0 0 0 RIP 0 0 RIP RIP 2733 F3G2 N4 F2 F3G2 RIP RIP 0 RIP 0 0 RIP 0 2734 F3G3 F2G2 F3G3 F3G3 F3G2 F3G2 F2G2 F3G2 F2 F2G1 F3G1 F3E3 2735 F3G3 N4 F3G3 F3G3 F3G2 F3G2 F2G2 F2G1 F2G1 F2G1 F3G1 F3E3 2736 F3G3 F3G2 F3G2 F3G3 F3G2 F3G2 F2G2 F3G1 RIP F2G1 F3G2 F3G3 2740 K4 F3G2 K4 F3G3 F3G3 N4 F2G2 F3G2 F2G1 F2G1 F3G1 F3G3 2741 F3G3 F3G2 F3G3 F3G3 F3G2 K4 F2G2 F3G1 RIP F2G1 F3G1 F3E2 2742 K4 N4 F3G3 F3G3 F3G2 F3G3 F2G2 F3G2 F2G1 F2G1 F3G2 F3G3 2743 K4 F3G2 F3G3 F3G2 F2G1 F2G1 F2G2 F3G2 F2G1 F2G1 F3G1 F3E2 2744 F3G3 F3G2 F3G3 F3G3 F3G2 F3G2 F1G1 F3G2 F1G1 RIP F3G1 F3E2 2745 F3G3 K4 F3G3 F3G2 F2G1 F2G2 F2G2 F3G1 F1G1 RIP F3G2 E2F2 2746 F2G1 F2G2 F3G1 F3G3 F2G1 F2G1 0 RIP 0 RIP F2 RIP 2749 0 0 0 0 0 0 0 0 0 0 RIP 0 2750 0 0 RIP 0 0 0 0 RIP 0 0 F1C1 RIP 2753 K2 G1 RIP 0 0 G1 0 0 0 0 RIP 0 2754 0 0 0 0 0 0 0 RIP 0 0 RIP 0 2756 F1G1 RIP RIP F3G2 RIP F2G2 RIP F3 0 RIP F2G1 F2E1 2760 0 G1 0 0 0 F1G1 0 RIP She · 0 RIP RIP 2762 0 0 0 0 0 0 0 RIP 0 0 RIP 0 2771 K4 F3G2 F3G3 F3G3 F3G2 F3G2 F3G3 F3G2 F1G1 RIP F3G2 F3G3 2772 RIP RIP F2 F1G1 RIP F1G1 0 RIP 0 0 RIP F1E1 2777 RIP G1 F2 F1G1 RIP RIP RIP F2 0 0 F2G1 RIP 2778 0 0 RIP 0 G1 0 0 RIP 0 RIP F2 RIP 2779 0 0 RIP 0 0 0 0 RIP 0 0 RIP 0 2781 0 0 RIP 0 0 0 RIP F2 0 0 F2 0 2783 RIP 0 RIP F1G1 RIP 0 G1 F2 0 F2G1 F2G1 RIP 2784 F3G3 F3G2 F3G1 F3G3 F3G3 F3G2 F3G3 F3G3 F1G1 F2G1 F3G2 F3E3 2787 RIP RIP F2 F2G1 RIP RIP RIP RIP 0 RIP F2 F1E1 2788 F3G3 F2G2 F3G3 F3G3 F3G3 F3G2 F3G2 F3G2 F1G1 RIP F3G2 F3E3

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36

II. Table (continued)

Effect on vegetation

Pre-emergence effect Post-emergence effect

Serial number of compound C / 3 'SKI Q 3 Celosia plumosa bromus inermis Setaria italica Raphanus sativus beta vulgar Setaria italica Medicago sativa Avena sativa Raphanus sativus beta vulgar Lycopersicon esculentum 2790 K4 F3G3 F3G3 F3G3 F3G2 F3G3 F3G2 F3G2 F2G2 F2 F3G1 F3E3 2795 F2G2 F1G1 F2 F3G2 F2G1 F1G1 RIP F2 RIP 0 F2G2 RIP 2796 RIP 0 F2 F3G2 F1G1 F1G1 0 RIP 0 0 F2 RIP 2798 0 0 0 0 0 RIP 0 F3 0 F1G1 F2G2 F3E2 2799 F1G1 RIP F2G1 F1G1 0 F1G1 F1G1 F3G1 RIP G1 F2G1 F2E1 2800 0 0 0 0 0 0 RIP F2 0 F1G1 F2G1 RIP 2801 0 G1 RIP 0 RIP RIP 0 0 0 0 RIP 0 2802 F2G2 RIP F2G1 F3G2 F2 F2G1 RIP F3G2 0 RIP F2G1 F3E2 2803 F3G3 F2G1 F3G3 F3G3 F3G2 F3G1 RIP F2G1 0 RIP F3G1 F3E3 2818 F2G2 F2G1 F2 F3G3 F2G2 F2G2 F1G1 F2G1 RIP 0 F3G1 F2E2 2819 0 0 0 G1 0 RIP 0 F2 0 Fi F2 F2 2822 K4 F3G2 F3G3 F3G3 F3G3 F3G3 F2G2 F3G2 F1G1 RIP F3G2 F3E3 2844 F2G3 F3G2 F3G3 F3G3 F2G3 F2G2 F3G2 N1G2 F1G2 F2G2 F2G3 F3G3 2845 K4 F3G3 F3G3 F3G3 F3G2 F3G2 N2G2 F3G3 0 N1G2 F2G3 F3G1 2850 0 0 0 0 0 0 - - - - - - 2851 0 0 0 0 0 0 0 N2 0 N1G1 F2 0 2852 0 0 0 0 0 0 0 0 0 0 F1G1 0 2853 F2G1 F1G1 F3 F3G3 F1G1 F2G1 0 0 0 0 RIP 0 2854 K4 K3G3 F3G3 F3G3 F2G2 F3G3 N2G1 F2G1 N1G1 N1F1 F2G2 F3 2855 F3G3 F3G2 F3G2 F3G2 F1G1 F2G2 NI F2 NI N1G1 F2G1 F2 2859 K4 K4 F3G2 F3G3 F3G2 K4 N2G2 F3G1 0 0 F2G2 N1F2 2862 RIP 0 RIP RIP 0 0 N1G1 0 0 0 F2G1 F2 2863 RIP 0 0 0 0 0 0 RIP 0 0 F2 0 2879 F3G3 F1G1 F3G2 F3G2 F2G2 F3G3 N2G1 RIP 0 0 F2G1 F2G3 2882 K4 F3G2 F3G3 F3G3 F3G2 F3G3 N1G2 F2G2 F2 RIP F2G2 F3 2883 K4 F3G3 F3G3 F3G3 F3G3 K4 N2G2 F2G1 NI N1G1 F1G1 F2 2885 F3G3 F2G2 F3G3 F3G3 F3G2 F3G3 N3G2 F2G1 N1G1 G1F1 F1G2 F2 2896 F3G3 F1G1 F3G2 F3G2 F2G2 F2G2 N2G3 0 NI 0 F2G2 F3G3 2898 0 0 RIP 0 0 0 0 0 0 RIP F2G1 RIP 2914 0 0 0 0 0 0 0 F1G1 0 F1G2 F1G3 NI 2923 0 0 RIP RIP 0 0 0 RIP 0 0 N1G2 0 2954 0 K1G1 RIP 0 0 0 0 N1G1 0 G1 F2G3 RIP 2987 0 0 0 0 0 0 0 0 0 0 F1G1 0 2992 F1G1 K2F2 F3G1 F2G2 0 K2G1 0 RIP 0 0 F2G3 NI 2994 0 0 RIP 0 0 0 0 0 0 0 F3G1 0 2995 0 0 F2 0 RIP 0 0 0 G1 0 F2G1 G1 2996 K3G3 F2G2 F3G2 F3G2 K2F1 K2G2 0 0 0 F1G1 F3G2 N1F2 2997 RIP G1 F2 F2G2 RIP RIP 0 F2G2 G1 F1G1 F2G2 F3 2998 0 0 0 0 0 0 0 0 0 0 RIP RIP 2999 0 0 0 0 0 0 0 0 0 0 F2 0 3000 0 0 0 0 0 0 0 0 0 0 F2G1 NI 3001 0 0 0 0 0 0 . 0 0 0 0 F2G2 G1 3002 K4 K4 F3G3 RIP F2G1 F1G2 0 N1G1 0 F1G1 F3G3 RIP 3006 F1F1 F1G1 F3G1 F2G1 G1 F1G1 0 RIP 0 0 F2G2 0 3017 0 0 0 0 0 0 0 0 0 0 F1G1 RIP 3018 K3G3 G2 F2G1 RIP F2G1 F1G1 0 0 0 0 F2G3 0

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38

II. Table (continued)

Effect on vegetation

Pre-emergence effect

Post-emergence effect

The compound

number Digitaria sanguinali Celosia plumosa bromus intermis Setaria italica Raphanus sativus beta vulgar 3019 F1G2 F2 F2 F2G1 G1 RIP 3022 F2G2 F3G1 F3G2 F1G1 F3G3 F2G2 3023 F2G2 F3G3 F2G2 F2G2 F2G1 F1G1 3024 0 0 0 0 0 0 3025 RIP RIP RIP 0 0 0 3026 RIP G1 F2 0 0 0 3027 0 0 0 0 0 0 3108 F3G3 F3G2 F3G2 F3G3 F3G3 F3G3 3109 F3G3 F3G2 F3G3 F3G3 F2G2 F2G2 3116 RIP RIP F2 F2G1 F1G1 RIP 3137 F3G3 F2G2 F3G3 F3G3 F2G1 0 3146 F3G3 F2G2 F3G3 F3G3 F2G2 F2G2 3147 RIP 0 RIP 0 0 0 3151 RIP F1G1 F2G1 F2G1 RIP RIP 3152 0 0 0 0 0 0 3153 RIP 0 F2 F2G1 F1G1 F2G2 3158 F1G1 F2G1 F3G1 F3G1 F2G2 F3G3 3159 F3G2 F2G2 F3G2 F3G2 F3G2 F3G2 3160 F2G2 F1G1 F3G1 F3G2 F2G2 F2G2 3180 F3G3 F3G3 F3G3 K4 F3G2 F3G3 3181 F3G3 F3G2 F3G3 F3G3 F2G2 F3G2 3182 F3G3 F3G2 F3G3 F3G3 F3G2 F3G2 3183 F3G3 F2G2 F3G3 F3G3 F2G2 F2G2 3184 RIP 0 RIP 0 0 0 3185 F2G2 RIP F2 F3G2 FI * F1G1 3186 0 0 0 0 0 0 3187 RIP RIP F2 F2G1 G1 F1G1 3194 F1G1 F2 F3G1 F3G3 F2 F2G1 3195 F2G2 F2G1 F3G1 F3G3 F2G1 F2G1 3196 F3G3 F3G2 F3G3 F3G3 F2G2 F2G2 3210 F2G2 F2G2 F3G3 F3G3 F2G2 F3G2 3284 F3G3 F3G2 F3G3 F3G3 F3G2 F3G2 3285 RIP RIP F2 F2G1 0 F2G1 3290 F3G3 F3G3 F3G3 F3G3 F3G2 F3G2 3349 K4 F3G3 K4 K3G3 F3G2 F3G3 3350 F2G1 F2G2 F3G3 F3G2 F2G2 F2G2 3352 F3G2 F2G2 F3G3 F3G2 F2G2 F3G2 3358 K4 F2G2 F3G3 F3G2 F3G2 F3G2 3577 K4 F3G3 F3G3 F3G2 F3G3 K4 3578 K4 F3G3 K4 F3G3 F3G3 F3G3 3579 K4 K4 F3G3 F3G3 F3G3 K4 3580 K4 F3G2 F3G3 F3G2 F3G3 F3G3 3581 K4 K4 F3G3 F3G3 F3G2 F3G3 3582 F3G3 F3G3 K4 F3G2 F3G2 F3G3 3676 0 0 0 0 0 0 3716 F1G1 F2 F3G1 F2G1 F2G1 F2G1

Setaria italica Medicago sativa Avena sativa Raphanus sativus beta vulgar lycopersicum esculentum 0 0 0 RIP F3G2 F2G2 0 NI NI N1G1 F2G1 0 N1G1 N1G2 RIP F1G1 F2G2 F2G1 0 0 0 0 F2G2 0 0 0 0 0 F1G1 0 0 0 0 0 F2G2 0 N1G1 0 0 0 F2G1 N2 N1G2 F3G2 N1F1 F2G2 F2G2 F2G1 N2G1 F3G2 N1F1 F2G1 F2G2 F2G1 NI N1G2 0 NI F2G1 N1F1 0 F3 NI F2G1 F2G2 F3 N2G2 N3G2 RIP N1G2 N2G3 F3 0 0 0 NI F2G2 F2 N2G1 RIP RIP RIP F2G2 F2 NI 0 0 0 RIP 0 G1 RIP 0 0 RIP F2 G1 F3G1 0 F2 F2G3 F2G1 N1G2 F3G2 RIP F2 N4 F3G1 N1G2 F2G1 0 F2 F2G2 F3 N1G1 F3G2 F2 F2 F2G3 F3 N1G2 F3G2 F2G1 F2G1 F2G2 F3 N1G2 F3G2 F3G2 F2G1 F ^ Gl F3 N2G2 F3G3 N1G1 N2G2 F2G3 N2G1 0 0 0 RIP RIP 0 0 RIP 0 RIP F2 F2 0 F2 0 0 F2 RIP 0 0 0 0 N2G2 F2 F2G1 F2G2 RIP F2 F3G1 F3 0 F2G1 0. RIP F3G1 F3 N1G2 F2G1 0 RIP F2G2 F3 N2G3 F3G2 N1G2 RIP N3G3 F3 F3G2 F2G2 F3G2 F3 F2G3 F2 0 F3G2 0 Fi F3G2 NI N1G2 F3G2 F2G1 F2G1 F3G3 F2 N1G2 F3G3 F1G1 F3G2 F3G2 N1F1 F1G1 F2G2 F1G1 F3G2 F2G2 F3G1 0 F3G2 0 F1G3 N3G2 F2G1 F2G1 F2G3 RIP C1G2 F3G2 F4 G2 F3G2 F1G2 F2G1 F3G3 F3 F1G2 F3G2 F1G3 F1G1 F3G3 F3 G2 F3G2 F1G2 F2G1 F3G3 F3 G2 F3G2 F1G3 F2G2 F3G3 F3 G2 F3G2 F1G2 F2G1 F3G3 F3 G2 F3G2 F1G2 F2G1 F3G2 F3 0 0 0 0 RIP 0 F1G1 F2 __ G2N1F1 F3G2 F2N1G1

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Example 24

Seed max seeds are sown in a greenhouse of 30 cm x 25 cm x 7.5 cm polystyrene foam bowls. Subsequently, the agent containing 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide, 2,2, 1,1 and 0, as the active ingredient, was sprayed onto the soil in the seeded bowls as described in Example 23. 55 kg / ha of the active substance. Plants that emerge from the soil produce 4-6 small leaves instead of the usual three leaves. Similar results are obtained when using small amounts, for example 0.0625% of the core weight.

Example 25

The active ingredients of the compounds of formula (I) are shown to be plant growth regulators in soybean (Salt max) and tomato (Lycoperase sicum esculentum). In the first case, the number of bean pods increases, in the second case, the yield increases. In a demonstration experiment, Salt max (Evans variety) and Lycopersicum esculentum (Tiny Tim variety) plants were grown in 12 cm diameter bowls (one plant per liter) filled with greenhouse soil (2 parts humus, 1.5 parts sand, 1, 5 parts peat to which is added 2.25 kg of 12-12-6 fertilizer and 2.25 kg of fine ground clay per 0.76 m ³ ). Aqueous spray broths are prepared and the plants in the bowls are sprayed with 374 l / ha of spray juice at a rate of 1.12 kg, 280 g and 70 g of active ingredient per hectare. The spray is prepared by dissolving the appropriate plant growth regulator in 15 ml of acetone and adding 2 ml of a solvent emulsifier mixture containing 60% by weight of a commercially available polyethoxylated vegetable oil emulsifier (96% by weight, Emulphor EL-719), 20% by weight. It contains% x and 20% by weight of deodorized kerosene. The volume of the mixture was adjusted to 80 ml by the addition of 0.156 wt% aqueous liquid non-ionic dispersant solution (90 wt% trimethyl nonyl poly (ethylene glycol ether) Tergitol ΤΜΝ-10). For each application rate, plants are sprayed with 374 liters of water per hectare for comparison, and the number of bean pods and yields are expressed as a percentage of the arithmetic mean of untreated plants Measurements are taken approximately three weeks after spraying. The degree of growth control observed on the plants is given on a scale from 0 to 10 (0 = no effect and 10 = maximum effect).

III. Spreadsheet

Growth regulating effect on two plant species

Serial number of compound Quantity kg / ha Salt max Lycopersicum esculentum Number of bean pods (% compared to untreated plants) Growth regulating effect (average) Yield growth (% compared to untreated plants) Growth Regulatory Impact (Average) 597 1.12 171 ^{a, c} 9 400 ^b 9 0.28 l ₇₇ a, c 4.5 291 7 0.07 151 2 436 1.5 1686 1.12 137 3 36 0 0.28 120 0.5 36 0 0.07 94 0 145 0 2005 1.12 169 ^{a, c} 9 255 ^b 9 0.28 163 ^{a, c} 7.5 327 7.5 0.07 160 3 364 3.5 2322 1.12 107 0.5 145 0 0.28 103 0 218 0 0.27 94 0 182 0 2324 1.12 97 0 73 1 0.28 114 0 109 0 0.07 97 0 36 0 2474 1.12 146 ^{a, c} 9 300 ^a 9 0.28 154 7.5 382 ^e 8.5 0.07 115 3.5 191 4.5

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42

III. Table (continued) Growth regulating effect on two plant species

Salt max Lycopersicum esculentum

Quantity kg / ha Number of bean pods (% compared to untreated plants) Growth regulating effect (average) Yield growth (% compared to untreated plants) Growth regulating effect (average) 1.12 157 ^{a, c} 8.5 136 ^d 7.5 0.28 135 3.5 191 2.5 0.07 104 1 164 0.5 1.12 163 ^{a, c} 9 109 ^{a, b} 9 0.28 166 ^a ' ^c 5.5 327 7.5 0.07 140 1.5 327 3.5 1.12 120 2 145 0.5 0.28 111 0 182 0 0.07 103 0 145 0 1.12 118 1.5 237 ^c 5 0.28 115 1 245 1.5 0.07 107 0 82 0 1.12 115 3 327 1 0.28 98 0 109 0 0.07 95 0 136 0 1.12 121 6.5 273 5.5 0.28 104 1.5 245 1 0.07 95 0 164 0 1.12 159 ^c 8 273 ^d , e 8.5 0.28 136 3.5 191 2.5 0.07 95 0.5 136 0 1.12 173 ^a 9 436 ^{d, e} 9 0.28 138 3.5 245 3.5 0.07 127 1 355 0.5 1.12 173 ^c 8.5 300 ^e 8 0.28 130 4.5 327 5 0.07 113 0.5 164 0.5 1.12 130 ^{a, c} 9 191 ^{a> b} ' ^d 9 0.28 133 4.5 436 4.5 0.07 130 1.5 355 0.5 1.12 147 6 327 ^{a, d} 9 0.28 141 2.5 273 ^e 2.5 0.07 104 1 245 0 1.12 101 2 382 ^d 7.5 0.28 101 0 245 ^e 1.5 0.07 92 0 109 0 1.12 144 8.5 300 ^d 8.5 0.28 144 2.5 273 ^e 1.5 0.07 124 0.5 327 0.5 1.12 129 ^{a, c} 9 300 ^a 9 0.28 129 5.5 245 5.5 0.07 112 2.5 300 1

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44

Table III (continued) Growth regulating effect on two plant species

Salt max Lycopersicum esculentum

Quantity kg / ha Number of bean pods (% compared to untreated plants) Growth regulating effect (average) Yield growth (% compared to untreated plants) Growth regulating effect (average) 1.12 143 ^c 7.5 218 ^{d, e} 7 0.28 149 2.5 245 1.5 0.07 126 0.5 300 0 1.12 144 8 273 ^d 8.5 0.28 170 2.5 245 ^c 3.5 0.07 113 0 191 0.5 1.12 124 7.5 245 ^d 9 0.28 127 3 245 ^e 3 0.07 104 0 382 1 1.12 147 ^c 7.5 327 ^{a, d} 9 0.28 130 2.5 355 ^e 4.5 0.07 138 0 300 1.5 1.12 19 l ^a ' ^c 9 364 8.5 0.28 l ₈₀ a, c 5 218 6.5 0.07 169 2 255 3 1.12 124 1.5 355 1 0.28 101 0 82 0 0.07 96 • 0 136 0 1.12 132 3 191 1.5 0.28 126 1 109 0 0.07 110 0 164 0 1.12 159 ^c 9 273 ^{a, d} 9 0.28 156 5.5 300 2.5 0.07 136 1.5 355 1 1.12 111 8.5 150 3 0.28 * 120 2 133 0 0.07 111 0.5 150 0 1.12 153 8.5 100 0 0.28 147 4 167 0 0.07 141 1 150 0 1.12 123 5.5 133 1 0.28 120 1.5 167 0.5 0.07 120 0 117 0 1.12 168 7 183 1.5 0.28 159 2.5 67 0 0.07 141 1 83 0 1.12 138 8 83 2 0.28 129 7 33 0.5 0.07 123 1.5 67 0 1.12 174 7.5 183 1.5 0.28 174 5 100 0.5 0.07 153 2 117 0

-22184 120

Yield growth (% compared to untreated plants)

III. Table (continued) Growth regulating effect on two plant species

Salt max

Lycopersicum esculentum

Application rate kg / ha

Number of bean pods (% compared to untreated plants)

Growth regulating effect (average)

Growth regulating effect (average)

1.12 159 7.5 100 0 0.28 156 3 117 0 0.07 108 0.5 83 0 1.12 171 8.5 50 1 0.28 177 4.5 150 0 0.07 132 1 100 0 1.12 147 8 33 0.5 0.28 132 3.5 133 0 0.07 99 0 83 0 1.12 180 9 67 2 0.28 159 6.5 67 0.5 0.07 165 2.5 183 0 1.12 159 ^c 6 286 ^b 8.5 0.28 115 3.5 200 2.5 0.07 105 1 229 1 1.12 169 ^c 4.5 243 ^b 8.5 0.28 150 1.5 271 5 0.07 131 1 171 1.5 1.12 169 ^c 6.5 229 ^b 8 0.28 150 2.5 271 5 0.07 131 1 171 1.5 1.12 137 • 3.5 200 5 0.28 108 1 157 0.5 0.07 92 0 114 .0 1.12 150 ^{a, c} 9 171 ^{b) d} 8.5 0.28 169 5.5 243 5.5 0.07 143 2 271 2 1.12 150 4.5 186 2.5 0.28 108 1 100 0.5 0.07 96 0 57 0 1.12 134 6 143 2 0.28 127 2.5 214 0.5 0.07 96 0 186 0 1.12 137 3.5 186 2.5 0.28 140 1 143 0.5 0.07 108 0 129 0 1.12 137 2.5 171 3 0.28 150 1 171 0.5 0.07 124 0 114 0 1.12 105 2.5 143 1 0.28 99 0 186 0 0.07 96 0 86 0

-2 347

184,120

III. Table (continued) Growth regulating effect on two plant species

Compound Quantity serial number kg / ha

Salt max

Number of bean pods (% compared to untreated plants)

Lycopersicum esculentum

Growth regulating effect (average)

Yield growth (% compared to untreated plants)

Growth regulating effect (average)

3018 1.12 108 3.5 129 2 0.28 105 0.5 157 0 0.07 115 0 129 0 3350 1.12 131 ^{a, c} 9 129 ^d 7.5 0.28 150 4.5 243 2 0.07 118 1.5 214 2 3022 1.12 124 3.5 143 2.5 0.28 108 0.5 129 0 0.07 92 0 114 0 3023 1.12 127 4.5 157 3.5 0.28 124 1.5 143 1 0.07 99 0 157 0 2418 1.12 150 3.5 103 3.5 0.28 125 1 169 1 0.07 125 0 94 0 Notes; (a) harmful d) rapid growth (b) distorted fruit (e) pear-shaped fruit (c) reduced sleeves

Example 26

Different varieties of plants are grown in 10 cm diameter greenhouses in greenhouses. Spray is then made from the active ingredient 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide and the plants in the bowls are sprayed at 374 L / ha (1.12 kg, 280 g, 70 g). and 17.5 g of active ingredient per hectare. Spray broths are prepared by dissolving the appropriate amount of 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide in 15 mL of acetone and adding 2 mL of a solvent emulsifier mixture (60% w / w). containing polyethoxylated vegetable oil emulsifier (96% active ingredient, Emulphor EL-719), 20% xylene and 20% deodorized kerosene, and the volume is adjusted to 80 ml by adding 0.156% by weight. aqueous non-ionic dispersant solution (90% by weight of t-methyl nonyl polyethylene glycol ether in Tergitol TMN 10). Two replicates at each application rate. Spray plants for comparison with 374 liters of water per hectare.

The following growth regulating effects have been investigated and evaluated:

epinasty leaf-thinning patching effects on new shoots.

The sum of the effects is given on a scale of 0 to 10, with 0 representing ineffectiveness and 10 representing maximum effect. The results are shown in Table IV. table.

-24184 120

49 50 Description of the effect Plant varieties, growth rate and condition ARC. Spreadsheet Heaven. kg / ha Effect degree Setaria italica 1.12 0 No visible effect Between 25 and 30 cm, 6-7 leaves 0.28 0 0.07 0 0.0175 0 Sorghum vulgare 1.12 0 No visible effect DeKalb E-57 0.28 0 30-37.5 cm, 6 leaves 0.07 0 0.0175 0 Zea mays, DeKalb XL — 373 1.12 0 No visible effect 40-45 cm, 6-7 leaves 0.28 0 0.07 0 0.0175 0 Hordeum vulgare, Larker 1.12 0 No visible effect 25-30 cm, 4-5 leaves 0.28 0 0.07 0 0.0175 0 Oryza sativa, Labelle 1.12 0 No visible effect 15-20 cm, 3-4 leaves 0.28 0 0.07 0 0.0175 0 Salt max, Williams 1.12 9 22.5-27.5 cm, 2 triple foils 0.28 9 At 1.12 kg, new leaves are much smaller. epinastine and a 1/2 letter 0.07 4 on the trunk, forming effect on leaves, color of leaves 0.0175 1 darker green Gossypium herbaceum, 1.12 3 Stonville 213 0.28 0 The leaves are more upright than horizon- 20-25 cm, real leaves 0.07 0 they are located in a row 3 of them developed 0.0175 0 Arachis hypogaea, 1.12 3 Florunner 0.28 0 15-20 cm, 6 leaves 0.07 0 0.0175 0 The leaves withered, weak epinasty Medicago sativa, Kansas 1.12 8 Epinasty, a shaping effect on a new shoot; some Lomma 0.28 3 a new shoot with a shaping effect on the trunk 0.07 0 0.0175 0 Linum usitatissimum, Linott 1.12 2 Poor growth in armpit 15-17.5 cm, 26-32 leaves 0.28 0 0.07 0 0.0175 0 Beta vulgar, Great 1.12 8 shaping effect on leaves (twist), stuttering, Western 0.28 5 new growth inhibited 12.5-15 cm, 4 true leaves 0.07 4 0.0175 0 Brassica napus, Torch 1.12 7 Shaping effect on new shoots, stunting 12.5-15 cm, 4-5 true leaves 0.28 4 0.07 2 0.0175 0 Phaseolus vulgaris, UI-114 1.12 9 Epinasty, leaves wither, formative effect on new female 35-40 cm, 3-4 trifoliate leaves 0.28 8 vekményre. Applying larger amounts of satiety- 0.07 5 of age 0.0175 3 26

-25184 120

52

ARC. Table (continued)

Plant varieties, growth rate and condition Heaven. kg / ha H ^at á ^s rate description of the effect Phaseolus vulgaris, Topcrop 1.12 9 Epinasty, leaves wither, formative effect on new female 27.5-32.4 cm, 3 trifoliate 0.28 9 as a result, the earlier development of the bean, stunting is greater letter 0.07 8 at 1.12 and 0.28 kg / ha, the new gear 0.0175 3 much of its growth will cease Cucumis sativus, Marketer 1.12 3 27.5-32.5 cm, 4 true leaves 0.28 0 0.07 0 0.0175 0 Cucumis job, Hearts of Gold 1.12 2 Saturation, growth of armpits is inhibited 22.5-27.5 cm, 3-4 true leaves 0.28 0 0.07 0 0.0175 0 Citrus vulgar, Congo 1.12 1 20-25 cm, 3 true leaves 0.28 0 Small increase in fruit yield. 45 cm Indian 0.07 0 there are melons. 0.0175 0 Raphanus sativus, Scarlet Globe 1.12 2 12,5-17,5 cm, 4-5 true leaves 0.28 1 In case of large quantities, forming effect on new leaves 0.07 0 0.0175 0 Caucus carota, Gold Spider 1.12 2 7.5-10 cm, 3-4 true leaves 0.28 1 Shaping effect on leaves. 0.07 0 0.0175 0 Allium cepa, Yellow Bermuda 1.12 0 12.5-15 cm, 2 leaves 0.28 0 No visible effect 0.07 0 0.0175 0 Beta vulgar, Detroit 1.12 9 Strong wilting and decay of leaves. The leaves are autumn- Dark Red 0.28 9 szesodródnak 10-12.5 cm, 4-5 true leaves 0.07 9 0.0175 8 Lactuca sativa, Black 1.12 0 Seeded Simpson 0.28 0 No visible effect 0.07 0 0.0175 0 Lycopersicum esculentum, 1.12 9 Shaping effect on new mail for every employee Tiny Tim 0.28 8 quantity, leaf infestation within 24 hours, earlier and na- 17.5-20 cm, 6-8 genuine 0.07 8 better yield (8-10 tomatoes per hand) leaf, flowering (6 weeks) 0.0175 7 1 to 2 tomatoes). Example 27 but it was impossible to quantify the final results. July 18th Williams sown Seed max seeds on 15 May 50 we found that most affected areas Missouri state soil. The growth rate applied most advanced plants containing it suffered from airborne active ingredient of a conditioning product 1- (2-carbomethoxy-benz- more damage. On August 8, we examined the zolyl) -2-methyl-4-phenyl-3-thiosemicarbazide, which was treated with two in the less damaged areas and found different amounts (1.12, 0.28, 0.07, that the amount of 0.28 kg / ha of active ingredient used on 18 July 0.0175 and 0.0044 kg / ha) at different times, so July 7 55 due to the presence of grains that are adequate for the on July 18, July 27, and August 8. Each size and number of seeds in the pods, in particular: at the applied amount, we repeated the more than one third of plants. Counting it set up for four different soil fertilization) runs. July 15- showed that the number of seed pods in the treated plants was I have severe ice damage to the plots, the plants are out- 60 today an average of 109, compared to untreated plants

-26184 120 pots with 86 sockets. The plants were 75-83 cm tall at the time of spraying, blooming and already had 8-10 small pods on each plant. On September 7, we found that both the treated and untreated plots had essentially outgrown the ice sheet. Although some of the stems are bent or broken, new shoots have grown and more kernels have developed. The treated plants, in particular the beans sprayed with 0.28, 0.07 and 0.0175 kg / ha of active agent, remained green and contained many full pods up to the top of the plants. The color of untreated plants began to change, which meant that the beans had stopped growing and ripening had begun.

In a similar experiment, Williams Salt Max seeds were sown in plots on May 30 in Kansas, and plants were treated on July 28 with 0.07 and 0.28 kg / ha of the previous agent. In August, a marked increase in the pods was observed. On September 5, they were ripe, flowering and pod production stopped. Pods and beans were counted on three untreated untreated air plants and also on three untreated untreated plants. The results are summarized as follows:

Quantity applied,

kg / ha 0 0.07 0.28 Number of pods per plant 54 81 64 number of beans per plant 132 212 181 plant growth 0% 61% 37 '

In another parcel experiment (Kansas State) about 200 km south of the above site, York Seed Max seeds were sown in 36 cm rows on July 10 after the wheat was harvested. The hatched plants were sprayed with an agent containing 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide on 24 August at 0.07, 0.14 and 0.28 kg / ha. . At the time of spraying, the plants were about 51 cm tall, budded and flowered. On September 7th, we examined the plants and found them green, still sprouting and flowering. At random, 5 to 5 plants were selected from each treatment and the pods on the plants were counted. The results are as follows:

Application rate, _{kg / ha} 0 0.07 0.14 0.28

Total pods 109,184,183,177 plants

Percentage increase 0 69% 67% 62%

Example 28

Among the active compounds listed in the table above, compounds with valuable and useful plant growth regulating activity were also prepared and tested for effects on other plant species, such as Avena sativa (oat) and, in some cases, Triticum aestivum (wheat), the seeds were treated with agents containing the following compounds:

2790 2882 3146 2822 2883 3180 2844 2885 3181 2845 3108 3210 2854 3109 3284

Claims (14)

Patent claims A plant growth regulator composition comprising up to 80% by weight as an active ingredient of a 1-benzoyl-3-thiosemicarbazide derivative, optionally in the form of a salt thereof, having the formula: R is -COR ¹ or hydroxymethyl: R ^{1 is} hydroxy, -NR ', R', C 1 -C 12 alkoxy, C 1 -C 6 haloalkoxy, phenyl (C 1 -C 4 alkoxy), (C 1 -C 4 alkoxy) - , (C 14 -alkoxy) or (C 1 -C 4) -alkoxy, (C 14 -alkoxy) - (C 14 -alkoxy) -, R 'is hydrogen, (C 1 -C 12) alkyl, (C 3 -C 6) cycloalkyl or phenyl (C 1 -C 4) -alkyl; C 1 -C 6 -alkoxy) or C 1 -C 6 -alkyl) or C 14 -C 14 alkoxy-C 14 -C 14 alkoxy; - R is hydrogen or (C1-C6) -alkyl; or - R and R together with the nitrogen atom to which they are attached form piperidyl; R ^{2 is C} 1-4 alkyl, nitro, trifluoromethyl or halogen; Ar is naphthyl, benzyl, (C 14 alkyl) benzyl or a group of the formula: - R ^{5 is C} 14 alkyl or halogen, provided that both ortho positions cannot be substituted by alkyl; - R ^{6 is C} 14 alkylthio, nitro, C 1-4 alkoxycarbonyl, benzyloxy, di- (C 1-4 alkyl) amino or C 1-4 alkoxy or trifluoromethyl; group; -27184 120 - n is 0.1, 2 or 3; q is 0 or 1, provided that the sum of n and q is not more than 3; m is 0, 1 or 2; R ^{3 is} hydrogen, (C 1 -C 4) -alkyl, (C 3 -C 4) -unsaturated, (C 1 -C 4) -hydroxyalkyl, phenyl or benzyl; and R ^{4 is} hydrogen or C 1 -C 4 alkyl, solid carriers or diluents, preferably potassium dihydrogen phosphate, chalk and silica, liquid diluents and solvents, preferably xylene, and surfactants, preferably polyoxyethylene / 5-soybean, sodium naphthalene-formaldehyde condensate, trimethyl-nonyl-poly (ethylene glycol) ether and sodium diisopropylnaphthalenesulfonate, together with at least one. 2. The pesticidal composition according to claim 1, wherein the active ingredient is a 1-benzoylthiosemicarbazide derivative having the formula (I): R, R ² and m are as defined in claim 1, R ^{3 is} hydrogen, C 14 alkyl, C 3 -C 4 unsaturated alkenyl, 2-hydroxyethyl, phenyl or benzyl; R ^{4 is} hydrogen or (C 1 -C 3) -alkyl, Ar is naphthyl or a group of formula (a): Each R ⁵ is independently C 1-4 alkyl, chloro, bromo or fluoro, with the proviso that both ortho positions cannot be substituted by alkyl; - ^R6 carboethoxy or dimethylamino group; and - n and q are as defined in claim 1. Embodiment according to claim 1 or 2, characterized in that it contains as active ingredient a 1-benzoyl-3-thiosemicarbazide derivative wherein Ar in the formula (I) is phenyl and R, R ² , R ³ , R ⁴ and m is as defined in claim 1. 4. An agent according to any one of claims 1 to 3, characterized in that it contains as an active ingredient a 1-benzoyl-3-thiosemicarbazide derivative, optionally in the form of a metal salt thereof in Group IA of the Periodic Table of Formula I - R is -COOR ¹ ; R ^{1 is} hydrogen or C 1-4 alkyl; and R ² , R ³ , R ⁴ , m and Ar are as defined in claim 1. 5. An embodiment of the agent according to any one of claims 14, wherein the active ingredient is a 1-benzoyl-3-thiosemicarbazide derivative having the formula (I): - R ³ is methyl; and R, R ² , R ⁴ , m and Ar are as defined in claim 1. 6. An agent according to any one of claims 1 to 5, characterized in that it contains as an active ingredient a 1-benzoyl-3-thiosemicarbazide derivative having the formula: wherein R ^{4 is} hydrogen and - R, R ² , R ³ , m and Ar are as defined in claim 1. As claimed in claim 1. 7. An agent according to any one of claims 1 to 6, characterized in that it contains as an active ingredient a 1-benzoyl-3-thiosemicarbazide derivative having the following general formula (I): - Ar (a); - n is 0; and - R, R ', R ³ , R ⁴ , m, Ar, and R ⁵ , R ⁶ and q are as defined above As claimed in claim 1. 8. An agent according to claim 1 wherein the active ingredient is an 1-benzoyl-3-thiosemicarbazide derivative, optionally in the form of a salt of a Group IA metal of the periodic system, wherein R -COR ¹ ; R ^{1 is} hydroxy or C 14 alkyl; and R ² , R ³ , R ⁴ , m and Ar are as defined in claim 1. 9. The agent of claim 1 wherein the active ingredient is an 1-benzoyl-3-thiosemicarbazide derivative having the formula: wherein R ^{13 is} hydrogen or C 14 alkyl. 10. The agent of claim 1, wherein the active ingredient is an 1-benzoyl-3-thiosemicarbazide derivative having the formula: wherein: - R ⁷ is -OH or -NR "R, R" and R "'is hydrogen or methyl; - R ⁸ is methyl or nitro, chloro or fluoro; - R ^{9 is} hydrogen, (C 1 -C 4) -alkyl, (C 34) -alkenyl which does not contain tx, p-unsaturation, or benzyl; - Ar is naphthyl, methylbenzyl or phenyl containing from 1 to 3 methyl, bromine, chlorine or fluorine substituents, with the proviso that both ortho positions on the phenyl cannot be substituted with methyl, and - R ^{10 is} hydrogen. or C 1-3 alkyl. -28184 120 11. The agent of claim 1 wherein the active ingredient is 1- (2-carbomethoxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide. 12. The agent of claim 1, wherein the active ingredient is 1- (2-carboxybenzoyl) -2-methyl-4-phenyl-3-thiosemicarbazide. 13. An agent according to claim 1 wherein the active ingredient is the potassium salt of 1- (2-carboxybenzoyl) -2-10-methyl-4-phenyl-3-thiosemicarbazide. 14. Process for the preparation of 1-benzoyl-3-thiosemicarbazide derivatives of the formula I and their agriculturally acceptable salts - in the formula I R is -COR ¹ or hydroxymethyl; - R ^{1 is} hydroxy, -NR, R, C 1 -C 12 alkoxy, C 1 -C 6 haloalkoxy, phenyl (C 1 -C 4 alkoxy) - (C 1 -C 4 alkoxy) - (1- C1-C4 alkoxy or C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkoxy; - R is hydrogen, (C 1 -C 12) alkyl, (C 3 -C 6) cycloalkyl or phenyl (C 1 -C 4) alkyl, where the phenyl is (C 1 -C 4) -alkyl, halogen, C 1-4 -alkoxy, (C 1-6 -alkoxy) - (C 1-6 -alkyl) or (C 1-4 -alkoxy) - (C 1-4 -alkoxy) -, (C 1-4) -alkyl may be substituted; R 'is hydrogen or C 1-6 alkyl; obsession R 'and R together with the nitrogen atom to which they are attached form piperidyl; R ^{2 is C} 1 -C 4 alkyl, nitro, trifluoromethyl, or halogen; - Ar is naphthyl, benzyl, (C 1 -C 4) alkyl-benzyl or a group of the formula: - R ^{5 is C} 1 -C 4 alkyl or halogen, provided that both ortho positions cannot be substituted by alkyl; - R ^{6 is C} 1-4 alkylthio, nitro, C 1-4 alkoxycarbonyl, benzyloxy, di- (C 1-4) alkyl) amino or C 14 alkoxy or trifluoro; methyl; - n is 0, 1, 2 or 3; q is 0 or 1, provided that the sum of n and q is not more than 3; m is 0,1 or 2; R ^{3 is} hydrogen, C 14 alkyl, - C 34 alkenyl, unsaturated, C 14 hydroxyalkyl, phenyl or benzyl, and R ^{4 is} hydrogen or C 14 alkyl; characterized in that the compound of formula (II) is reacted with a phthalic acid derivative of formula (III) or (IV) - R ¹ , R ² , R ³ , R ⁴ , m and Ar are as defined in claim 1 and X is a cleavable group - and optionally neutralizing the resulting benzoyl-3-thiosemicarbazide derivative, wherein R is -COOH, to form the corresponding agriculturally acceptable salt.