JPH0466868B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] (However, in the formula, R each independently represents a lower alkyl group, a phenyl group, a lower alkyl group substituted with a halogen atom, or a phenyl group substituted with a halogen atom, and X and Y each independently represent a hydrogen atom, It represents a halogen atom, a lower alkyl group, or a trifluoromethyl group, and m represents an integer of 0 to 2. When m is 2 in Xm, that is, two Xs are two different groups or two of the same type. This invention relates to isonicotinic acid anilide derivatives represented by the following formula, a method for producing the same, and a plant growth regulator comprising these compounds. The plant growth regulating action of the compound of the present invention effectively inhibits the growth of monocots or dicots. In other words, the effective growth inhibitory effect on gramineous crops is due to the development of healthy seedlings,
It is useful for preventing lodging during harvest, promoting carbohydrate production by promoting photosynthesis, and increasing yield by increasing the amount of fertilizer used. In addition, the appropriate growth control effect on grass not only improves the aesthetic appearance by turning the leaves dark green, but also saves mowing labor and costs, and also helps maintain the shoulders of highways, green belts, and railroad tracks. It also helps prevent the dangers associated with The compound of the present invention represented by the general formula [] is a new compound, and the compound represented by the general formula [] A benzhydrol derivative represented by the formula (wherein X, Y and m have the same meanings as above) is acylated with a corresponding carboxylic acid or a reactive derivative thereof, such as an ester, an acid chloride, an acid anhydride, etc. It can be obtained by The compound represented by the general formula [] can be produced by a known method, for example, according to JP-A-57-188571. Appropriate conditions for the reaction are selected depending on the reactive derivative of the acid, but generally it is carried out in an inert solvent such as benzene, toluene, methylene chloride, dioxane, tetrahydrofuran, dimethylformamide, etc., and in the presence of a deoxidizing agent such as potassium carbonate. , carbonated soda,
The process proceeds smoothly by using caustic potash, caustic soda, triethylamine, pyridine, etc. Furthermore, pyridines can be used advantageously since they act as both a solvent and a deoxidizing agent. The reaction temperature is generally preferably 0 to 40°C,
Depending on the progress of the reaction, heating may be carried out as appropriate. Synthesis Example Isonicotinic acid [4-chloro-2-(α-acetoxybenzyl)]anilide (compound number 12) Add 3.4 g of isonicotinic acid-[4-chloro-2-(α-hydroxybenzyl)]-anilide to 30 ml. Dissolve in pyridine, cool with ice water, and add 1.3 g of acetyl chloride dropwise while stirring. After the addition is complete, the mixture is stirred for about 2 hours while returning to room temperature. After the reaction is complete, pyridine is distilled off under reduced pressure, and water is added to the resulting residue to obtain crude crystals. This was recrystallized from ethyl acetate to obtain 3.5 g of the desired product. Melting point 160-162℃ Elemental analysis value: C ₂₁ H ₁₇ ClN ₂ O ₃ Assuming molecular weight 380.82 C H N Calculated value (%) 66.23 4.50 7.36 Experimental value (%) 66.28 4.45 7.41 General formula obtained in this way [] Since the compound represented by has an asymmetric carbon atom in the molecule, isomers exist. Such isomers can be resolved by known methods. Next, representative examples of the compounds of the present invention are shown in Table 1. In addition, in Table 1, the positions of substituents X and Y are as follows.

【table】

[Table] *1) in Table 1 above: NMR (in CDCl ₃ ) δ
(ppm) 2.2 (S, 3H), 7.1 (S, 1H), 7.25-8.65
(m, 12H), 9.65 (S, 1H) The plant growth regulator of the present invention contains one or a mixture of two or more compounds represented by the general formula ().
Usually 30~1500g per 10ares, preferably 50~
It is appropriate to use it at a rate of 1000 g, but it goes without saying that the dosage can be adjusted as appropriate depending on the use situation, purpose of use, and plant situation. For example, when treating stems and leaves, it is appropriate to use 50 to 1000 g per 10 ares, and when treating seedling boxes (30 cm x 60 cm x 3 cm), use 2 to 100 g per 10 ares (per 20 boxes). In addition, for formulation, it can be mixed with various solid and liquid carriers used in the preparation of general agricultural chemicals to produce wettable powders, emulsions, powders, granules, flowables, etc. The carrier referred to herein may be either solid or liquid, or a combination thereof. Examples of these include talc, clay, bentonite, kaolin, diatomaceous earth, calcium carbonate, wood flour, starch,
Gum arabic, water, alcohol, kerosene, naphtha, xylol, xylene, cyclohexanone,
These include methylnaphthalene, benzene, acetone, etc., as well as adjuvants used in drug formulations, such as spreading agents, emulsifiers, dispersants, wetting agents, adsorbents, thickeners, antifoaming agents, antifreeze agents, Polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate ester salts, petroleum as physical property improvers, etc. Sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonates, aliphatic amine salts, quaternary ammonium salts, alkylpyridium salts, alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, phosphorus Examples include isopropyl acid, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose, ethylene glycol, xanthan gum, and the like. However, it goes without saying that the embodiments of the present invention are not necessarily limited to the above-mentioned dosage forms. In addition, when formulating the formulation, the mixing ratio is determined by the general formula ()
Compound represented by 5-50%: Adjuvant 0-12%:
45-95% carrier is optimal. In addition, in the present invention, various insecticides, fungicides,
Herbicides, plant growth regulators, acaricides, nematicides,
By using it in combination with attractants, repellents, plant nutrients, fertilizers, etc., a wider range of effects can be expected. The chemical of the present invention may be used, for example, at any time during the sowing period, seedling period, or growth period, and depending on the target plant, treatments such as spraying on the ground, water surface or soil, and immersion can be performed. Next, the effects of the present invention will be explained in detail by showing experimental examples. Experimental example 1 Growth inhibition test by pre-germination soil treatment on various plants A pot of 1/5000 are was filled with clay loam,
After sowing bentgrass, cucumber, komatsuna, cyperus, mehishiba, rice, and corn, the soil was shallowly covered with soil. A hydrating powder of the test compound prepared according to the formulation in Example 1 was diluted with water, and a predetermined amount of The active ingredient was sprayed with a small sprayer at 250g or 500g per 10 ares. In the survey, plant height was measured 50 days after spraying. The results are shown in Table 2. The effect values shown in Table 2 represent the following levels of plant growth inhibitory activity. 0: Growth inhibition rate of 0-10% compared to untreated area 1: 〃 11-20% 〃 2: 〃 21-30% 〃 3: 〃 31-40% 〃 4: 〃 41-50% 〃 5: 〃 51% or more

[Table] Experimental Example 2 Pre-germination soil treatment on rice seedlings to prevent growth of rice seedlings A ^100cm2 pot was filled with clay loam, and 40 grains of germinating fir (rice variety: Nipponbare) were sown in it and shallowly covered with soil. An emulsion of each test compound prepared according to the same recipe was diluted with water to obtain a predetermined amount of active ingredient.
It was sprayed with a small sprayer at 2000g and 500g per 10 ares. In the survey, plant height, root length, leaf age, stem and leaf weight, and root weight were measured 25 days after spraying. The exam is
The experiment was carried out in a phytotron (plant growing device) at 25-30°C. The results are shown in Table 3. The values shown in Table 3 are the average values of 40 individuals, and the weights are dry weights.

【table】

[Table] Examples of the present invention are shown below, but the compounds, carriers, and proportions used are not limited to these examples. Example 1 Compound No. 4 50 parts by weight Sodium alkyl sulfate 2.5 Polyoxyethylene alkyl phenyl ether
2.0 〃 Clay 45 〃 Mix these thoroughly until homogeneous and pulverize to obtain a wettable powder. Example 2 Compound No. 12 10 parts by weight Sodium ligninsulfonate 1 Bennite 30 Talc 59 These are thoroughly mixed until uniform and granulated to obtain granules. Example 3 Compound No. 20 10 parts by weight polyoxyethylene alkyl phenyl ether
7 Calcium alkylaryl sulfonate 3 Xylene 60 Cyclohexanone 20 These are thoroughly mixed and dissolved until uniform to obtain an emulsion. Example 4 Compound No. 6 5 parts by weight Clay 95 parts by weight The above ingredients were mixed and pulverized to obtain a powder. Example 5 Compound No. 11 10 parts by weight ethylene glycol 5 xanthan gum 0.2 polyoxyethylene sorbitan monooleate
5 〃 Water 79.8 〃 The above is wet-pulverized to obtain a flowable agent.

Claims (1)

[Claims] 1. General formula (However, in the formula, R each independently represents a lower alkyl group, a phenyl group, a lower alkyl group substituted with a halogen atom, or a phenyl group substituted with a halogen atom, and X and Y each represent a hydrogen atom or a halogen atom. , represents a lower alkyl group or a trifluoromethyl group, m represents an integer of 0 to 2. In Xm, m
When is 2, that is, two X's mean two different groups or two groups of the same type. ) isonicotinic acid anilide derivatives. 2 General formula (However, in the formula, X and Y each independently represent a hydrogen atom, a halogen atom, a lower alkyl group, or a trifluoromethyl group, and m represents an integer of 0 to 2. When m is 2 in Xm, that is, 2 X means two different groups or two groups of the same type.) A general formula characterized by acylating a benzhydrol derivative represented by (However, in the formula, R each independently represents a lower alkyl group, a phenyl group, a lower alkyl group substituted with a halogen atom, or a phenyl group substituted with a halogen atom, and X, Y and m are the same as above. A method for producing an isonicotinic acid anilide derivative represented by: 3 General formula (However, in the formula, R each independently represents a lower alkyl group, a phenyl group, a lower alkyl group substituted with a halogen atom, or a phenyl group substituted with a halogen atom, and X and Y each independently represent a hydrogen atom. ,
It represents a halogen atom, a lower alkyl group, or a trifluoromethyl group, and m represents an integer of 0 to 2. Xm
When m is 2, that is, two X's mean two different groups or two groups of the same type. )
One or two isonicotinic acid derivatives represented by
A plant growth regulator characterized by containing seeds or more as an active ingredient.