CA1297894C - Benzamide derivative, process for its production and plant growth regulant - Google Patents

Abstract

ABSTRACT
A benzamide derivative of the formula:

Description

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~ur E~ef.: HC-45 BENZAMIDE DERIVATIVE, PROCESS FOR ITS PRODUCTION AND PLANT
GROWTH REGULANT
The present invention relates -to a benzamide derivative, a process for its production and a plant S grow-th regulant containing it.
In the case of rice or wheat, it happens not infrequently that the crop plants are lodged by wind or rain immediately before -the harvest time, whereby the yield drops substantially. There have been proposed some chemical compounds which are intended to regulate the stems to be short and strong against such lodging force.
However, there have been problems such that an attempt to control the stems to make them sufficiently strong, is likely to adversely affect -the panicles, or the effectiveness of such treatment is very much influenced by the weather, the growing state or the timing or season for the treatment.

In the case of a lawn or hedge trees, or grass in a non-agricultural field, even if such plants are neatly trimmed or mown, they tend to grow quickly again. There - . .

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have been some drugs tested for e-ffe~4e~e-s~ so that ~ 0~'~3 cut-ting or mo:n~ may be thereby ommitted. However, a satisfactory cornpound has no-t yet been available.
In the case of fruit -trees, a thinning agent is frequen-tly used to preven-t the fruit trees from bearing so many fruits tha-t the fruits tend to be small in size.
However, the range of application is very narrow, and the method for its use is very difficult.
On the other hand, it is also an importan-t area to increase the number of flowers or fruits.
In the case of root-crops, the quality of the root degrades when flower stalk develops. Therefore, a compound to control the development of the flower stalk is desired.
In the case of sugar cane, it has been attempted to increase the yield by preventing the heading or by increasing the sugar content by some physiological action.
Further, in the case of potatoes or onions, it is important to delay the sprout during their s-torage.
The above instances are merely exemplary, and there may be many other areas where the growth of plants is desired to be con-trolled. In each area, there may be some compounds which are actually used. ~lowever, there has been no compound which is fully satisfactory. It is therefore desired to develop an improved compound.
The present inventors have conducted extensive research on the herbicidal and plant grow-th regula-ting , . . .
.

activities of various compounds and have found that certain benzamide derivatives exhibit various interesting activities including herbicidal activities against various plants, activities to shorten stems, to promote tillering, 5 to control development of fresh-buds or in some cases to promote development of axillary buds. On the basis of f~rfher ' ~ ~ this discovery, a furhter study has been made, and as a result, the present invention has been accomplished.
The present lnvention provides a benzamide derivative of the formula:
Cl Cl ~ NHCO ~ CH2cR (I) wherein R is hydroxyl, alkoxy, alkoxyalkoxy, alkoxyallcoxyalkoxy, alkenylalkoxy, alkenylalkoxyalkoxy, alkynylalkoxy, alkynylalkoxyalkoxy, monoalkylamino, dialkylamino or O-cat wherein cat is an inorganic or organic cation.
The present i.nvention also provides a plant growth regulant comprising an effective amount of a benzamide derivative of the formula I and a carrier, and use of a compound of the formula I as a plan-t growth regulant.
Further, the present invention provides a process for producing a benzamide derivative of the formula I, which comprises reacting 4-hydroxy-N-(2,3~dichlorophenyl)~benzamide with a compound of the formula XCH2COR wherein R is as defined above and X
is a halogen atom, or reacting . . .

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4-(2,3-diclorophenyl-carbamoyl)-phenoxyace-tyl chloride with a compound of the formula RH wherein R i5 as defined above.
Now, the present invention wiLl be described in detail with reference to the preferred embodimen-ts.
In Table 1, representative compounds of the present invention are given. These compounds will be referred to hereinafter by the compound numbers identified in Table 1.
Table 1 10 ' : No. Chemical formula MeltiOg poin-t lS 1 Cl Cl ~ ~( NHCO ~ OCHz 003 198 - l99.S

~ OCD2COOC2H5 126 - 129 ~~ -NHCO ~ OCH2COOC3H7-n 131 - 135 NHCO ~ oCH2CooC3H7-i l3C - 132 -NHCO ~ -OCH2COOC4Hg-n 132 - 136 -NHCO ~ OCH2COOC4Hg 114 - 118 Table 1 (Continued) Compound Chemical formula _ MeltiOng point Cl Cl _ 7 ~ -NHCO ~ OCH2COOC4Hg-t 149 - 150.5 8 ~ NHCO ~ 'COC~ 1 158 - 161 Cl Cl 9 ~ -NHCO ~ OCH2cOocl2H25 153 - 158 Cl Cl ~ -NHCO ~ CH2 CH OC4H9-n 87 - 92 11 ~ -NHCO ~ OCH COOCH CH2- 65 - 70 Oc~2cH2o~4H9-n 1~ ~ ~Cl ~ ~ NHCO ~ OCH2COOCH2CH= 124 - 1127 13 Cl Cl ~ NHCO ~ -OCH2COOCH~CH= 135 - 139 . Cl Cl ~
I~ NHCO ~ OCH2COOCH2C-CH 95 - 101 Table 1 (Con-tinued) S No. Chemical formula Meltigg point Cl Cl ~ NHCO ~ OCH2CONHCH3 196 - 197.5 15 L ~ ~ OC 8 - 1 ~ NHCO ~ OCH2CONHC3H7-n 170 - 171.5 : .... __, 25 L NHC0 ~ OcH2co~uc~7~;

Cl Cl 35 ~ ~ _ ~ ~ 'CH2cONHc4H9-n L41 - 142 .20 ~ NHCO ~ OCH2cONHc4Hg~ O 170 - i71 2l ~ NHC0 ~ 'CH2CONHC4Hg-t =

50 L ~

Table 1 (Continued) . ~ . .. __ Compound Chemical formula MeltiOg point Cl Cl 23 ~ ~ OCH2CON < CH 136 - 138 Cl Cl 24 ~ -NHCO ~ -OCH2CON / 2 5 145.5 - 147 21 25 ~ -NHCO ~ -OCH2CON\ 3 7 133 - 140.5 Cl Cl 26 ~ -NHCO ~ OCH2CON\ 3 128 - 130.5 Cl Cl 27. ~ -NHCO ~ -OCH2CON\ 4 140.5 - 144 Cl Cl 28 ~ -NHCO-~OCH CON/ 4 9 143.5 - 146 Cl Cl 29 ~)-NHCO-~>-OCH2COONa More than 230 _ Cl Cl ~ -NHCO- ~ OCH2COOH. 153 - 157 : N ( C2H5 ) ~ ( Decomp . ) 71~4 Table 1 (Continued) _ Compound Chemical formula MeltiOg point 31 ~ -NHCO ~ OCH2COOH. 203 - 207 2 3 7 (Decomp.) 32 ~ -NHCO- ~ -OCH2COOH. 150 - 154 NH2 4 9 (Decomp.) The benzamide derivatives of the present invention can readily be obtained in good yields by reacting 4-hydroxy-N-(2,3-dichlorophenyl) benzamide with various esters or amides of a haloacetic acid, in an organic solvent such as acetone, toluene, dioxane or N,N-dimethylformamide in the presence of an inorganic base such as potassium carbonate or sodium carbonate or an organic base such as pyridine or triethylamine.
Otherwise, they can be obtained by reacting 4-hydroxy-N~(2,3-dichlorophenyl)-benzamide with a haloacetic acid, in an aqueous solution in the presence o~
an inorganic base such as sodium hydroxide or potassium hydroxide to obtain 4-(2,3-dichlorophenylcarbamoyl)-phenoxyacetic acid (Compound No. 1), reacting this compound with an inorganic halide such as thionyl chloride or an organic halide such as phosgene in an organic solvent such as dioxane or toluene to convert i-t to i-ts acid chloride derivative, and . .

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g then reacting this acid chloride derivative with various alcohols, alkoxyalcohols, alkoxyalkoxyalcohols, alkenylalcohols, alkenylalkoxyalcohols, alkynylalcohols, alkynylalkoxyalcohols, monoalkylamines or dialkylamines, in an aqueous solution or in an organic solvent such as acetone, toluene or dioxane in the presence of an inorganic base such as potassium carbonate or sodium carbonate or an organic base such as pyridine or triethylamine.
EXAMPLE 1 (Preparation of Compond No. 2 in Table 1) 28.2 g of 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide, 20.0 g of ethyl bromoacetate and 20.7 g of potassium carbonate were dispersed in lS0 ml of N,N-dimethylformamide, and the dispersion was stirred at a temperature of from 120 to 140C for 4 hours. After completion of the reaction, the reaction solution was poured into 500 ml of a 2-% hydrochloric acid aqueous solution. The crude product obtained by collecting precipitates by filtration, was recrystallized from toluene -to obtain 34.5 g of desired ethyl 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetate. Yield:
93.4~ Melting point: 126-129C
EXAMPLE 2 (Preparation of Compound No. 1 in Table 1) 2.82 g of 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide and 1.67 g of bromoacetic acid were dissolved in 10 ml of dioxane. To this solution, a mixture of 0.97 g of sodium hydroxide and 2 ml of water was dropwise added over a ~ 78~

period of 10 minutes at a temperature of 20 C under stirring. A~ter the dropwise addition, the reaction solution was s-tirred at a temperature of 80C for 2 hours.
After completion of the reaction, the reaction solution was poured into 50 ml of water, and acidified wi-th hydrochloric acid. Then, the crude product obtained by collec-ting precipita-tes by filtration, was recrystallized from toluene/methanol -to obtain 2.5 g of desired 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetic acid.
Yield: 70.6~ Melting point: 198-199.5C
EXAMPLE 3 (Preparation of Compound No. 5 in Table 1) A mixture of 3.54 g of 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetic acid, 3.57 g of -thionyl chloride and 30 ml of dioxane was stirred at lS a -temperature of 80C for 4 hours. An excess amount of thionyl chloride and dissolved hydrochloric acid gas, sulfurous acid gas and dioxane were distilled off by a rotary evaporator to obtain 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetyl chloride as the residue after distillation.
On the other hand, 0.8 g of n-butanol and 2.0 g of triethylamine were dissolved in 20 ml of dioxane. To this solu-tion, a solution prepared by dissolving above 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetyl chloride in 5 ml of dioxane, was dropwise added over a period of 5 minutes at room temerature under stirring. Af-ter completion of the dropwise addition, the stirring was . . , ~D.2~78~a~

continued at room temperature for further 5 hours. After comple-tion of the reaction, the reaction solution was poured into 200 ml of a 2% hydrochloric acid aqueous solution. The precipita-tes were collected by fil-tration, 5 washed with a dilute alkaline aqueous solution and water, and dried. Then, the precipitates were recrystallized from toluene to obtain 3.3 g of n-butyl 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetate. Yield:
80.5~ as calculated on the basis of 10 4-(2,3-dichlorophenyl)carbamoylacetic acid) Melting point: 132-136C
EXAMPLE 4 (Preparation of Compound No. 18 in Table 1) 0.71 g of isopropylamine and 3.0 g of triethylamine were dissolved in 20 ml of dioxane. To this solution, a 15 solution prepared by dissolving 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetyl chloride prepared in the same manner as in Example 3 in 5 ml of dioxane, was dropwise added over a period of about 5 minutes at room temperature under stirring. After 20 completion of the dropwise addition, the stirring was continued at room temperature for further 5 hours. After completion of the reaction, the reaction solution was treated in the same manner as in Example 3 to obtain 3.8 g of desired 25 N-isopropyl-4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetamide.
A Yield: 92.5% as calculated on the basis of a~l 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetic ' ~ .

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Melting point: 159-161.5 C
E~AMPLE 5 (Preparation of Compound No. 30 in Table 1) 1.02 g of 4-(2,3-dichlorophenyl-carbarnoyl)-phenoxyacetic acid was dissolved in 5 ml of methanol. To this solution, 0.33 g of triethylamine was dropwise added over a period of about 5 minutes at room temperature under stirring. Further, the stirring was continued at room temperature for 1 hour. Then, excess amounts of triethylamine and methanol were distilled off by a rotary evaporator to obtain 1.2 g of the desired triethylamine salt of 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetic acid. Yield: 90.7% Melting point: 153-157C (Decomposed) The plant growth regulant of the present invention may be prepared in the form of e.g. a wettable powder, an emulsifiable concentrate, a liquid formulation, a granule, a dust, a flowable or an aqueous solution by mixing the active ingredient with various kinds of carriers depending upon its physicochemical properties.
Among such carriers, as liquid carriers, conventional organic solvents may be employed, and as solid carriers, .. . . . . . .
conventional mineral powders may be employed.
Further, during the preparation of such a formulation, a surface active agent may be added to impart emulsifiability, dispersibility and spreadability to the formulation. Further, the compound of -the presen-t invention may be, as the case requires, combined with a fertilizer, a herbicide, an insecticide or a fungicide in ~2~ 94 the form of a unitary formulation or as a tank mix for application.
As a carrier, an inert inorganic substance such as bentonite, clay, zeolite or talc may be used. As an organic solvent , a solvent in which various compounds are well soluble, such as xylene, toluene, cyclohexanone or a glycol may be employed. Further, as a dispersing agent, an emulsifying agent or a fixing agent, there may be employed an anionic or nonionic surface active agent such as lignin sulfonate, naph-thalene sulfonate, dialkyl sulfosuccinate, polyoxyethylene nonyl phenyl e-ther, polyoxyethylene s-tearyl ether or polyoxyethylene dodecyl ether.
When the compound of the present invention is used as a herbicide, the active ingredient is applied in a sufficient amount to obtain desired herbicidal effects.
The dose of the active ingredient is within a range of from 1 to 200 g/are, usually preferably from 5 to 50 g/are. It may be formulated into a formula-tion such as a wettable powder, an emulsifiable concentrate, a dust or a granule, which contains the active ingredien-t in an amount of from 0.1 to 80% by weight, preferably from 1 -to 50% by weight.
When the compound of the present invention i.s used as a herbicide, it mainly controls the germination and growth of weeds to eventually kill the weeds. In a paddy field, the herbicide of the present invention exhibits excellent herbicidal e~fects agains-t not only annual weeds such as barnyardgrass (Echinochloa oryzicola), but also perennial weeds such as sagittaria (Sagittar~a p~gmaea) and flat-sedge (Cyperus microiria). No substantial phytotoxicity to transplanted paddy rice plants has been observed. Also in soil treatmen-t or foliar treatment in an upland field, it exhibits selective herbicidal effects for corn (Zea mays), soybean (GlYcine max) or the like.
When the compound of the present invention is used as a plant grow-th regulant, it may be applied in a dose of the active ingredient within a range of from 0.1 to 100 g/are, usually preferably from 1 to 50 g/are depending upon the type of the crop plant, the type of the compound or the time of application. The active ingredient compound may be formulated into a formulation such as a wettble powder, an emulsifiable concentra-te, a dust or a granule, which contains from 0.1 to ~0% by weight, preferably from 1 to 50% by weight, of the active ingredient.
When the compound of the present invention is used as a plant growth regulant.
It is absorbed mainly from the foliage of plan-ts, and then transferred in -the plant body to exhibit its posf~
activities preferentially at the tu~ where the growth is most ac-tive. The exhibition of the activi-ties varies depending upon the compound, the concen-tration, the type of plants or the growing stage of plan-ts. However, it is ~7~

assumed -that the activi-ties are antagonistic against auxin or gibberellin as the plant hormone.
As specific effects, in the case of gramlneous plants, the shorteniny o~ the length between nodes is observed after the foliar treatment, and in some cases, tillering is facilitated. Further, with respect to broad leaf plants, the plan-t growth regulant of the present invention is effective to suppress the formation of new buds, to prevent spindly growth or to promote formation of axillar~
buds or flower buds.
Thus, the compound of the present invention has a wide range of applications, for example, as a lodging reducing agen~, as an agen-t for reducing the necessity of trimming hedge, as an agent for shortening flower trees, grasses or large weeds, or as a thinning agent.
When the compound of the present invention is used as a plant growth regulant in foliar treatment, the dose may usually be smaller than that required for a herbicide.
However, the dose varies depending upon the type of plants or the purpose of the use. For example, when it is used to reduce the lodging of plan-ts, it may be applied in an amoun-t of from 0.5 to 3 g/are in the case of rice and from 2 to 10 g/are in the case of wheats. When it is used to shorten plants, it may be used in an amount of from 3 to 15 g/are in the case of grasses such as Bermuda yrass, Erom 10 to ~0 g/are in the case of trees and from 20 to 50 g/are in the case of large weeds in a non-agricultural field. In soma cases, it may be used in an amount outside the above ranges. Whereas, when it is used as a thinning agent or to induce flower buds, the dose may be at a le~el of from O.l to l g/are.

Now, the present invention will be described in further detail with reference ~o Formulation ~xamples and Test Examples.

FORMULATION EXAMPLE 1: Preparation o~ wettable powder To 40 parts by weight of Compound No. 5, 52 parts by weight of kaolin clay and 3 parts by weight of white carbon were added, and the mixture was mixed and pulverized by a kneader. Then, 4 parts of a powdery sur*actant Sorpol* 503 ( trade mark, Toho Kagaku K.K.) and 1 part by weight of a powdery surfactant Rapizol BB-75 ~ trade mark, Nippon Oil and Fats Co., Ltd.) were mixed to obtain a wettable powder containing 40% by weight of Compound No. 5.

FORMULATION EXAMPLE 2: Preparation of emulsifiable concentrate 15 parts by weight of Compound No. 10 was dissolved in 42 parts by weight of xylene and 33 parts by weight of cyclohexanone, and 10 parts by weight of Sorpol 800A ( trade mark, Toho Kagaku K.K.) was added thereto and dissolved under stirring to obtain an emulsifiable concentrate containing 15% by weight of Compound Mo. 10.

FORMUL~TION EXAMPLE 3: Preparation of dust 5 parts by weight of a wettable powder containing 40% by weight of Compound No. 15 prepared in the same manner as in Example 1 was thoroughly mixed with 0.3 part by weight of Rapizol* BB-75 (* trade mark, Nippon Oil and Fats Co., Ltd.) and 94.7 parts by weight of clay to obtain a dust containing 2~ by weight of Compound No. 15.

FORMULATION EXAMPLE 4: Preparation of micro-~ranule formulation To 50 parts by weight of Compound No. 1, 3 parts by weight of whitP carbon and 47 parts by weight of kaolin clay were mixed, and the mixture was pulverized. Two parts by weight of the pulverized mixture was added to 96 parts by 1~ weight of fine particulate zeolite under stirring in a speed kneader. While the stirring was continued, 2 parts by weight of polyoxyethylene dodecyl ether diluted with water was poured thereto. The mixture was prepared with a small amount of water until no powder was observed. The mixture was withdrawn and then, dried under air stream to obtain a micro-granule formulation containing 1% by weight of Compound No.
1.

FORMULATION EXAMPLE 5: Preparation of granule To 50 parts by weight of Compound No. 3, 3 parts by weight of white carbon and 47 parts by weight of clay were added, and the mixture was pulverized by a kneader. Two parts by weight of the pulverized mixture, 40 parts by weight of bentonite, 43 parts by weight of clay, 5 parts ~ ~2~

by wei4ht of sodium tripolyphosphate and 2 parts by weight of a powder~ sur~actant Rapizol BB-75 ( trade mark, Nippon Oil and Fats Co., L-td.) were charged into a kneader, and the mixture was thoroughly mixed. Then, wa-ter was added thereto, and the mixture was thoroughly kneaded, ~ranulated by a granula-tor and dried under air stream to obtain granules containing 5% by weight of Compound No. 3.

TEST EXAMPLE 1:
A ~00 cm2 pot was filled with a paddy field soil.
Seeds of barnyardgrass (Echinochloa oryzicola), monochoria (Monochoria vaginalis) and bulrush (Scirpus juncoides) were uniformly sown in the soil surface layer and tubers of sagittaria (Sagittaria pygmaea) and cyperus (Cyperus serotinus) were planted. Water was introduced to a dep-th F~r~h~r of 3 cm. --Fur-htcr, two paddy rice seedlings of 2-leaf stage were transplanted. Then, a diluted solution of a wettable powder of each test compound was dropwise applied in a predetermined amount of each compound. On the 20th day after the application, the herbicidal effects against the weeds and -the response of the transplanted paddy rice plants to the -test compound were evaluated. The results are shown in Table 2.
The evaluation was made in accorclance wi-th the following standards.

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Herbicidal effect O: Same as no treatment 1: 20% control 2: 40% control 3: 60% control 4: 80~ control 5: Comple-tely withered Phytotoxicity to crop plants -: No phytotoxicity ph,yfo1LoJ~lc +: Slight +: Minor phytotoxicity ++: Medium phytotoxicity +++: Serious phytotoxicity (These standards will be used for evaluation hereinafter.) ' .' ~ ' .

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TEST EXAMPLE 2: Upland soil treatment test A 400 cm2 pot was f illed with an upland soil, and seeds of slender amaranth (Amaranthus vlrl s), lambsquarters (Chenopodium album) and large crabgrass (Digitaria sanguinalis) were mixed with the surface soil, and seeds of wheat (Triticum aestivum), corn (Zea mays) and soybean (Glycine max) were sown in a depth of 3 cm.
AE-ter sowing, a diluted solution of each test compound was sprayed on the surface of the soil in a predetermined un~
~'~ 10 ~ ont of the compound. On the 30th day af-ter the -treatment, the herbicidal effects against the weeds and the responses of the crop plants to each test herbicide were evaluated by the same standards as in Test Example 1.
The results are shown in Table 3.

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E . ~ ~ _ r~ o 12~7894 Foliar treatment tests on various plants (plant qrowth regulant) ; Rice (Orvza sativa), barley (~ordeum vulgare), French bean (Phaseolus vulgaris L.) and lettuce were separately grown in porous pots of 60 cm2, and thinned depending upon the size of the plants. The growth degrees were adjusted to a level of from 2 to 3 leaf stage, and a diluted solution of each test compound was applied in an amount of 10 liter/a -to the foliage part of the plant by a spray gum. On the 30th day after the treatment, the growth inhibition was evaluated. The results are shown in Table 4.
The evaluation was made in accordance with the following standards:

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Growth inhibi~ion in height 0: Same as no treatment 1: Growth inhibition of about 20~ as compared with no treatment 2: Growth inhibition of about 40gO as compared with no treatment 3: Growth inhibition of about 60~ as compared with no treatment 4: Growth inhibition of about 80~ as compared with no treatment 5: No progress in growth observed since -the treatment Effects of the treatment G: Green deepening T: Tillering M: Malformed leaves B: Burning of leaves ~.2~ 9~

Table 4 Compound Concent- Test plants No. ration Response value (%) RI* BA* FR* LE*
.
0 .1 5 5 4 . 5MB 5 l 0 . 05 4T 5T 4 5 0.025 3 4 4 4 _ 0. l 5 4T 5B 5 2 0 . 05 4T 3 5 5 0.025 3.5 3 4 4 0.1 ,4.5T 4T 4.5MB 5 4 0 . 05 4 . 5T 4T 4 . 5M 5 0.025 4 3.5 4 4.5 _ 0 . l 5 4T 4 . 5M 4 25 f5 0. 05 5 4 4 4 0 . 0 25 4T 3 3 . 5 3 ... _ ..
0. l 4T 3 4 4 7 o o25s 2 2 2 2 .___ ._ 0.1 4 3 4 4 8 0.05 3 2 4 3.5 0.025 2 1.5 3 2 ..
0 . l 4T 4 . 5T 5MB 5 40 lO 0 . 05 4T 4T 4. 5M 5 _ 0 . 025 3 . 5 3 . 5 4 4 o 5 Table 4 (Continued) Compound Concent- Test plants No. ration Respons~ value (%) RI* _ BA* FR* LE*
0.1 4.5T 4T 5MB 4 12 0.05 4.5T 4 4.5 4 0.025 4 3.5 4 3.5 0.1 4 3 4 4 13 0.05 3 3 3 3.5 0.025 2 2 2 2.5 _ 0.1 4T 4T 4 3 14 0.05 '4 4 3.5 3 0.02S 3 3 3 2 0.1 5 5 5MB 5 0.05 4.5T 4T 4.5M 5 0.025 3.5 3 4 4 ._.
0.1 5 4T 5MB 5 17 0.05 4.5T 4T 4.5 5 0.025 4T 3.5 4 4 0.1 5 4T 4 4 19 0.05 5 4 4 4 0.025 4T 3.5 3 3.5 _ 0.1 5T 4 5MB 5 23 0.05 5T 4 4.5 5 0.025 4 3.5 4 4.5 :' ' ' ' '.' , 8~

Table 4 (Continued) Compound Concent- Test plants No. ration Response value RI* BA* FR* LE*
0.1 3 3 3 3 0.05 3 2.5 3 2 0.025 2 2 _ ~ 1.5 0.1 5T 5T 5MB 4 29 0.05 4 4 4 4 0.025 4 4 4 0.1 5 5 5MB 4 2Q 30 0.05 4T 4.5 4.5 4 0.025 3.5 4 4 3.5 Note:.* RI: Rice BA: Barley FR: French bean LE: Lettuce TEST EXAMPLE 4: Foliar treatment test on azelea A diluted solution of each tested compound was applied to azelea (Rhododendron indicum) nursery stocks (heigh-t:
25 - 30 cm) grown in a porous pot of 200 cm2 so that the entire nursely stocks were adequately wet (25 liter/a).
Seven days later, they were trimmed, and 2 months later, the evaluation was conducted by the same standards as in Test Example 3. The results are shown in Table 5.

,: .

~2~ 4 Table 5: Foliar treatment test on azelea Compound Concentration Growth Other response N~ ~ 1 inhibition 2 0.1 5 GB
lS 0.05 4 .
0:015 4 M

0.1 4.5 G
: 0.05 4 ._ 0.1 4 0.05 3.5 _ ._ l 0 05 3.5 :

:
. . . .
.

3L2~713~

TEST E~AMPLE 5: Foliar treatment test on wheat A field of wheat (Norin No. 61) sown in rows in early November, was divided into unit plots of 5 m x 2 m. Each compound diluted to a predeterrnined concentration was sprayed over the entire surface in a unit plo-t in an amount corresponding to 10 liter/a by means of a hand sprayer on l~ days prior to heading i.e. late April. The dust and micro-granule formulation were applied manually.
In middle June, the stem length, the panicle length and the number of panicle and the grain weight per unit area were examined with respect to 50 stems which showed average growth. The lodging degree was moderate at the non--treated plots, and the plots where the lodging reducing effect was distinctly observed was marked with O. The results are shown in Table ~.
The numeral values represent percentage values relative to the non-treated area, and the values in the brackets ( ) are actually measured values.

. . ~.

.
.
' -~7 ~9 Table 6: Foliar treatment tes-t on wheat . __ A 5 Compound Applied Stem Panicle ~lumber Grain a~,n9 ~_~ No. amount length length ~f weight reducing (g/are) (%) (%) ~laens~2 (%) effect Der m : 10 80 95 95 94 _ .
2% dust1082 97 100 96 O
of com- 5 85 100 98 100 O
pound 2 93 102 105 101 No. 15 1% 10 87 100 101 102 O
micro-granule5 93 98 102 104 compound 2 100 101 99 102 ~o. 1 Non- 100 100 100 100 treat- _ (95cm) (8.5(4502(4529 ment cm) /m ) /m ) LZ~1789~

TEST EXAMPLE 6: Foliar -treatment test on Bermuda qrass Bermuda grass (T-328 variety) was divided into plots of 1 m x 1 m. Five days after mowing, a diluted solution of each compound was uniformly applied in an amount corresponding to 10 liter/a to each plot by means of a hand sprayer. Ten days and 20 days after the application, the evaluation was conducted by the same evaluation standards as used in Test Example 3.
The change in the color of leaves was evaluated under the following standards:
Color of leaves Browning: Slight B-l Lit-tle B-2 Substantial B-3 Green deeping: Slight G-l Little G-2 Substantial G-3 The results are shown in Table 7.

.

~. .

Table 7: Growth inhibition on foliar treatment test on Bermuda grass .
~ompound Active lO days la-ter 20 days later ~o. ingredient (g/a) Inhibi- Color of Inhibi- Color of tionleaves -tion leaves 5 G-l 5 G-l 1 25.5 45 34~5 2 15 4,5 5 G-1 2.5 4 3 : 6 5.5 4.5 34 4.5 9 5 4.5 3 2.5 4 2 5 .G-2 5 G-1 5 G-l 4.5 2.5 4 3 ll 25.5 45 34 .
18 15 45 4.5 2.5 3.5 2 _ . .

.

Table 7 (Con-tinued): Grow-th inhibition on foliar treatment test on Bermuda grass Compound ~ctive10 days later 20 days later No. ingredient (g/a)Inhibi- Color of Inhibi- Color of tion leaves tion leaves _ 21 125,5 4.5 4.5 26 10 4.5 4.5 B-2 4.5 B-l : 27 52.5 2 B-l 29 125.5 4.5 25 G-1 30 _ 32 0 5 G-l 4.5 ~7~4 TEST EXAMPLE 7:
Foliar treatment test on paddy fleld rise A paddy field to which paddy field rice seedlings (Koshihikari) were transplanted by a transplanter, was divided into unit plots of 6 rows x 3 m. Each regulant diluted with wa-ter to a predetermined concentration was uniformly sprayed in an amount corresponding to 10 liter/a by a sprayer on 7 days prior to heading (A fixing agent was added -to a wettable powder and an aqueous solution.) After the harvest, the stem length, the panicle length and the panicle weight were measured with respect to 20 plants. The results are shown in Table 8.
The numerical values represent percentage values relative to the non-treated plots, and were rounded off to decimal place. Fur-ther, the lodging degree as observed was represented with a 5-step evaluation using 0 to 4.
Further, with respect to the representative plot, the length between nodes was measured. The results are shown in Table 9.

12~89~iL

Table 8: Foliar treatment test on rice .. _ _ 5 Compound g/are Ratio to no treatment Lodging Plot No. (A.I) (gO-) reducing No .
Stem Panicle Panicle effect length length weight 1 81 100 9~ 0 1 0.5 88 102 106 1 2 . 0.25 98 105 103 2 3 _ 2 C.5 96 99 98 2 5 0.25 101 100 99 3 6 -10 0.5 85 107 110 0 8 0.25 92 104 109 1 9 16 0.5 95 102 104 2 11 0.25 102 99 100 . 3 O12 29 0.5 86 102 108 0 14 0.25 94 106 104 1 15 .

0.5 87 97 105 0 17 0.25 96 106 103 2 18 ~0 ' . __ .. ~ _ No 100 100 100 3 treat- _ (80.5 (18.7 (3.41 ment __ cm) cm) g) 45`

~ ~78~

Table 9: Length between nodes of rice Plot Length between nodes relative to No. no treatment .... _ No Nl M2 N3 N4 . ...

. 10 97 57 96 94 102 _ No 100 100 100 100 100 treat- (3.45) (18-5) (13.7) (9.7) (3.8 ment cm) _ -~2~789A

TEST EXAMPLE 8: Foliar treatment tests on trees To a solution of an emulsifiable concentrate of Compound No. 10 having a predetermined concentration was applied to various trees grown in pots of 200 cm2 and 400 cm2 by means of a spray gun in an amount of 15 liter/a when new branches grew to a few cm after branches were trimmed. For spraying, the pot was placed in a box of 40 cm x 50 cm, and the mixture was uniformly sprayed in the box.
Three months later, the growth of the new branches were evalua-ted by the standards of Test Example 3. The results are shown in Table 10.
The height of the each tree at the time of spraying was as follows.
15 Azelea (Rhododendron indicum): 25 - 30 cm Box tree (Buxus microphylla): 20 - 25 cm Chinese hawthorn (Photinia glabra): 35 - 40 cm Abelia (Abelia serrata): 40 - 50 cm Spindle tree (Euonymus japonicus): 50 - 60 cm 20 Enkianthus perulatus: 30 - 35 cm Pomegranate (Punica granatum): 30 - 40 cm ~uniperus chinensis: 50 - 60 cm .

~2~78~4 Table 10: Growth inhibition of new branches of trees Compound No. 10 Concentration (gO) of ac-tive ingredien-t Trees 0.05 0.1 0.2 Rhododendron indicum 3.5 4.5 5 Buxus microphylla 2 4 4.5 Photinia qlabra 3 4.5 5 Abelia serrata 3 4 5 Euonymus jeponicus 2 ~ 5 Enkianthus perulatus 3.5 4.5 5 Punica qranatum 3 4 5 Juniperus chinenesis 0 2 4 TEST EX~MPLE 9: Foliar treatment test on radish To examine -the inhibition of flower stalk development of radish, a field of early maturing radish (Raphanus sativus) sown in spring and grown to immediately before flower stem development was divided into plots so that each plo-t contained 6 plants. The wettable powder and aqueous solution having a predetermined concentration, a nonionic surfactant was added so that the applied concentration would be 500 ppm, and the mixture was applied in an amount corresponding to 10 liter/a in the respective plots by means of a sprayer, and the micro-granule formulation were applied manually.
One month later, the evaluation on each plant was conducted in the same manner as in Test Example 3. The results are shown in Table 11. (The numerical value is an average of 6 plants, and is rounded off to two decimal places.) Table 11: Inhibition of flower stalk development of radish Com- Formulation type ~pplied amount Inhibi-poOund and content g/a tion Formula- Active -tion ingredient ......... _ .. . .
Micro-granule500 5 4 1 formulation 1%125 2.5 Wettable powder 10 5 4.7 S 50% 1 255 ~ i Emulsifiable 20 5 5 11 concentrate 10 2.5 4.1 25~5 1.25 3.2 Wettable powder 10 5 4.3 16 50%5 2.5 3.3 2.5 1.25 2.0 Aqueous solu-tion 5 5 4.7 29 100%1 25 1 25 3 b - . :

~2~t~8~
-- 4'1--TEST EXAMPLE 10: Non-agricultural field spraying test To examine the growth inhibition of large weeds, a field of miscanthus (Miscanthus sinensis) and goldenlod (Solidago altissima) grown luxurian-tly was divided into spray plots of 2.5 X 4 m. Diluted solutions of the wettable powder of Compound No. 1 (which contained 0.1%
fixing agent) and -the emulsifiable concentrate of Compound No. 10 were applied to the plots uniformly in an amount corresponding to 30 liter/a by means of a watering pot.
The average height and maximum height of miscanthus and goldenlod in the plots were measured at the time of the treatment and 3 months after the treatmen-t.
The results are shown in Table 12.

:

8!~)~
- ~5 -Table 12: Growth inhibition of weeds in non-agricultural field Com- g/are Height of weeds (cm) pound (A.I.) _ ¦

Miscan-thus Solldago At the 3 months At the 3 mon-ths ¦
treatment later treatment la-ter _ No 25 60 - 110 90 - 140 50 - 80 treat- _ 60 - 110 ~ /U '50 ~ U~

TEST EXAMPLE 11: Thinning test on apples Among branches of an apple tree (Fuji) of 25 years old, similar branches were selected, and 20 days after the full bloom, a solution of each compound having a predetermined concentra-tion was sprayed over the entire branches by means of a sprayer in such amount that the solution sprayed was not dropped from the branches. Two months later, the frui-t-bearing rate and -the side to side diameter were examined. The resul-ts are shown in Table 13.

~`` ~3L2~3789 Table 13: Thinning test on apples Com- Concent- Number of Test results pound ration tested fruits Ratio to no treatment No. (ppm) (%) Center Side Fruit bearing Average fruits fruits rate (%) fruit diameter Ratio to Center Side non-treated fruits fruits branch (%) ~0 . 39 120 71.88.3 111 1 25 32 101 87.59.9 114 : 12.5 37 11386.5 11.5 109 35 108 71.47.4 106 11 25 37 110 86.510.0 112 on 12.5 30 99 90.0 12.1 110 TNrea- 34 102 82.427.5 100 ted _ (35.9 mm) 35 plot __ , ' ' :

2~

TEST EXAMPLE 12: Foliar treatment test on suqar cane A field of sugar cane grown to the initial stage of ripening, was divided in-to plo-ts so that each plot contained 5 plants, and 30 ml of a solution having a predetermined concentration of an active ingredient was applied by a hand sprayer to the base portion of the top leaves of each stem.
Two months later i.e. at the time of harvesting, some heading was observed in the non-treated plot, whereas no heading was observed in each of the treated plots. The plants were harvested and squeezed, and the sugar con-tent of the pressed juice was measured by means of a polarimetric sugar content meter. The results are shown in Table 14.

Table 14: Results of measurement of sugar content of sugar cane 0 - Compound No. Active ingredient (~) Mean of sugar content (~) . _ 0.2 13.83 ~5 1 0.1 13.57 0.2 14.21 0.1 13.84 0.2 12.98 29 0.1 11.95 plot _ 10.39 ~78~4 TEST EX~MPLE 13: Foliar treatment tes-t on soybean In a green house, soybean (Enrei) was grown in a 200 cm2 pot (1 plant/pot). At the beginning of the 3 leaf stage, each compound diluted to a prede-termined concentration and having 500 ppm of a nonionic surfactant added, was applied in an amount corresponding to 10 liter/a. The test was conducted with 3 plants per plot.
Two months later, the number of pods formed were examined.
The results are shown in Table 15. (The numerical value is an average of 3 plants, and is rounded off to two decimal places.) Table 15 Compound No. Active ingredient (ppm) Number of pods 31.0 1 100 35.3 300 33.3 28.3 25 11 100 39.7 300 38.0 25.0 30 29 100 35.3 300 37.3 26.0 35 30 100 36.3 300 32.7 Non-treated _ 24.7 40plot , .:
, ` ' ' ' ' :
.
.

Claims (7)

1. A benzamide derivative of the formula:

(I) wherein R is hydroxyl, alkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, alkenylalkoxy, alkenylalkoxyalkoxy, alkynylalkoxy, alkynylalkoxyalkoxy, monoalkylamino, dialkylamino or O-cat wherein cat is an inorganic or organic cation.

2. The benzamide derivative according to Claim 1, which is selected from the group consisting of

3. A plant growth regulant comprising an effective amount of a benzamide derivative of the formula I as defined in Cla im 1 and a carrier.

4. Use of a benzamide derivative of the formula I as defined in Claim 1, as a plant growth regulant.

5. A process for producing a benzamide derivative of the formula:

(I) wherein R is hydroxyl, alkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, alkenylalkoxy, alkenylalkoxyalkoxy, alkynylalkoxy, alkynylalkoxyalkoxy, monoalkylamino, dialkylamino or O-cat wherein cat is an inorganic or organic cation, which comprises reacting 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide with a compound of the formula XCH2COR wherein R is as defined above and X
is a halogen atom, or reacting 4-(2,3-diclorophenylcarbamoyl)-phenoxyacetyl chloride with a compound of the formula RH wherein R is as defined above.

6. The process according to Claim 5, wherein 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide is reacted with the compound of the formula XCH2COR in an organic solvent in the presence of an inorganic or organic base.

7. The process according to Claim 5, wherein 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetyl chloride is reacted with the compound of the formula RH in an aqueous solution or an organic solvent in the presence of an inorganic or organic base.