JPH0676356B2 - Cyclohexane derivative and plant growth regulator - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel cyclohexane derivative and a salt thereof, and a plant growth regulator containing these as active ingredients.

(Prior Art) In so-called chemical control, in which the growth of plants is controlled by chemical substances, maleic acid hydrazide (MH), N, N-dimethylaminosuccinamide (daminogit) or 2-chloroethyltrimethylammonium has hitherto been used. Chloride (Chlormecoat) has been used for the purpose of suppressing plant growth, suppressing germination of lateral buds, or preventing lodging.
Further, the cyclohexane derivative that the present inventors have already found is known to be effective as a plant growth regulator (JP-A-58-164543 and JP-A-59-196840).

(Problems to be solved by the invention) These are not only limited in the application scene, the application plant and the application time, but also the effect is unstable, the drug damage occurs, and the price is further reduced. It had various drawbacks such as high cost. In addition, the lawn, pests, weather conditions,
In order to cope with various environmental stresses such as soil conditions, multiple varieties are often mixed-sown. Therefore, in order to alleviate the lawn mowing work, a growth regulator with little difference among varieties in growth inhibitory effect is desired.

As a result of earnest studies in view of the above demands, the present inventors have found that the cyclohexane derivative and the salt thereof of the present invention have little difference between lawn varieties even when compared with the above cyclohexane derivative,
Moreover, they have found that they are excellent plant growth regulators that have solved the drawbacks of the conventionally used plant growth regulators.

(Means for Solving Problems) The cyclohexane derivative of the present invention has the general formula [I] [Wherein R ¹ represents a hydrogen atom or a lower alkyl group, R ² represents a lower alkyl group, R ³ represents a hydrogen atom, an alkyl group, an alkenyl group, a hydroxyalkyl group, a cycloalkyl group, a morpholino group, an aminoalkyl group, N- alkylaminoalkyl group, N, N- dialkylaminoalkyl group, an alkoxycarbonylalkyl group, the formula ^{_{- (CH 2) l R 4}} ( wherein, R ⁴
Is a lower alkoxy group, a lower alkylthio group, a benzylthio group, an anilino group, a morpholino group, a piperazino group or a piperidino group which may be substituted with a lower alkyl group, l
Represents an integer of 2 or 3. ),formula (Wherein X represents a halogen atom, a lower alkyl group, a lower alkoxy group, a phenoxy group or an alkoxycarbonylalkyloxy group, m represents an integer of 0 or 1, and n represents 0 to 2
Indicates an integer. ), The formula —CH ₂ R ⁵ (wherein R ⁵ is a furyl group,
A tenyl group or a pyridyl group is shown. ) Or expression (In the formula, R ⁵ has the same meaning as described above.). ] Is represented.

The compound of the present invention represented by the general formula [I] may have the tautomeric structure shown below, but the present invention includes these tautomers. Further, the compound represented by the general formula [I] of the present invention can form a salt, which is also included in the scope of the present invention.

The compounds of the present invention represented by the general formula [I] are exemplified in Table 1. The compound numbers will be referred to in the following description.

The compound of the present invention can be produced, for example, as follows.

[In the formula, R ¹ , R ² and R ³ have the same meanings as described above. However,
In formula [II], when R ¹ is a hydrogen atom, in formula [I], R ¹
Indicates R ³ NH ₃ . Further, in the formula [II], R ¹ is a hydrogen atom, and in the formula [I] and the formula [III], R ³ is a formula. (X and m have the same meanings as above), the formula [I]
R ¹ represents a hydrogen atom. That is, it is produced by reacting the compound represented by the formula [II] with the amine represented by the formula [III] in the presence or absence of a solvent in the temperature range of room temperature to the boiling point of the solvent for 0.1 to 10 hours. be able to. Examples of the solvent include alcohol solvents such as methanol and ethanol, nonpolar solvents such as benzene, toluene and xylene, acetic acid ester solvents such as acetic acid methyl ester and acetic acid ethyl ester, and halogenated hydrocarbon solvents such as dichloromethane and chloroform. A solvent etc. are mentioned.

Next, examples will be described.

Example 1 (Production of Compound 20) 2.4 g (0.01 mol) of 3,5-dioxo-4-propionylcyclohexanecarboxylic acid ethyl ester and 0.9 g of aniline
(0.01 mol) was heated under reflux in 25 ml of ethyl alcohol for 2 hours. After the reaction was completed, the solvent was distilled off, and the obtained crystals were washed with petroleum ether and collected by filtration. The crude crystals were recrystallized with ethyl alcohol to obtain 2.0 g of yellow needle crystals having a melting point of 108-110 ° C.
The yield was 63.4%.

The compounds of the present invention 1 to 19 and 21 to 108 can also be produced according to the above-mentioned method. Next, production examples of salts will be shown.

Example 2 (Production of Compound 74) 2.0 g (9.42 mmol) of 3,5-dioxo-4-propionylcyclohexanecarboxylic acid and isopropanolamine
1.42 g (18.9 mmol) was added in ethyl acetate at room temperature. The precipitated crystals were separated and washed with ethyl ether to give the title compound as a yellow powder with a melting point of 140-143 ° C.
2.8g was obtained. The yield was 87.3%.

Next, the plant growth regulator of the present invention comprises a cyclohexane derivative represented by the general formula [I] or a salt thereof as an active ingredient. In order to use the compound of the present invention as a plant growth regulator, the compound of the present invention may be used as it is, but a carrier, a surfactant, a dispersant, an auxiliary agent and the like may be blended to prepare a wettable powder, a granule, Even better results can be obtained by processing into an emulsion, powder, fine powder, paste, or any other formulation form. The plant growth regulators having these formulation forms include talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermicillite, slaked lime, silica sand, ammonium sulfate, solid carriers such as urea, alcohols, dioxane, etc. Liquid carriers such as acetone, cyclohexanone, methylnaphthalene, dimethylformamide, dimethylsulfoxide, salts of alkyl sulfates, alkylaryl sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoal It is manufactured by appropriately using an emulsifier such as a chelate, a dispersant, or various auxiliary agents such as carboxymethyl cellulose and gum arabic. The mixing ratio of the active ingredient may be adjusted according to need, but in the case of granules, 0.5 to 20% (weight)
, Or 5 to 70% (by weight) when used as an emulsion or wettable powder
Is appropriate.

The plant growth regulator of the present invention is applied as it is, or in the form of being appropriately diluted or suspended with water etc., in an amount effective for controlling the growth of the plant. The amount of the compound of the present invention used as a plant growth regulator cannot be unconditionally specified due to differences in soil conditions, formulation form, time of use, method of use, type of cultivated crop or target plant, etc., but 10 g to 5 g per hectare
It is effective to apply it so that it becomes kg.

The plant growth regulator of the present invention can be used in combination with other pesticides or fertilizers, if desired.

Next, examples of the formulation of the plant growth regulator of the present invention will be described. In addition,% in a formulation means weight percentage.

Example 3 (Wettable powder) Compound (1) 10%, diatomaceous earth 85%, sodium dinaphthylmethanedisulfonate 2% and sodium ligninsulfonate 3% were uniformly mixed and pulverized to obtain a wettable powder.

Example 4 (Emulsion) Compound (8) 30%, cyclohexanone 20%, polyoxyethylene alkylaryl ether 11%, calcium alkylbenzene sulfonate 4% and methylnaphthalene 35.
% Is uniformly dissolved to obtain an emulsion.

Example 5 (Granule) Compound (21) 5%, lauryl alcohol sulfate sodium salt 2%, sodium ligninsulfonate 5
%, Carboxymethylcellulose 2% and clay 86% are uniformly mixed and ground. 20% of water is added to 80% of this mixture, and the mixture is kneaded, processed into granules of 14 to 32 mesh with an extrusion granulator, and dried to obtain granules.

Example 6 (Dust) 4% of the compound (31), 5% of diatomaceous earth and 91% of clay are uniformly mixed and pulverized to obtain a dust.

Example 7 (paste agent) 5% of the compound (15), 1% of xylene, 5% of polyoxyethylene sorbitan monolaurate and 89% of white petrolatum were uniformly mixed to obtain a paste agent.

(Action) The plant growth regulating action of the compound of the present invention represented by the general formula [I] is mainly a growth suppressing action, but is not limited to this, and applicable plant, applying method, applying period, applicable drug By varying the amount, various plant growth regulating effects are expressed. For example, rooting promotion, lodging reduction, lateral bud development, rooting promotion, foliage green retention, flowering promotion or delay, fruit setting promotion, seed ripening promotion, temperature damage and The herbicide has an action of reducing phytotoxicity or an action of increasing resistance to disease, but these various plant growth regulating actions are not always expressed simultaneously.

(Effects of the Invention) The compound of the present invention can improve seedling quality by applying it at the time of raising seedlings such as paddy rice and vegetables, and can produce healthy seedlings excellent in survival after transplantation and resistance to low temperature injury. . Moreover, by applying it to foliage during the growing season of paddy rice and wheat, the upper leaf blade length is shortened and the three-dimensional arrangement of the leaf blades is improved, resulting in higher light utilization efficiency. As a result, the ripening rate of these plants can be improved and the yield of cereals can be increased.
By applying to plant foliage or soil, internode elongation of rice, wheat, corn and the like can be suppressed to prevent or reduce lodging. Further, the application of the compound of the present invention can suppress the growth of flowers, garden crops and the like which are caused by high temperature and lack of sunlight in greenhouses and greenhouse cultivation.

The various plant growth regulating effects of the compound of the present invention are extremely useful not only in agriculture and horticulture but also in suppressing the growth of plants in non-agricultural land.

For example, grasses such as parks, playgrounds, golf courses, airports, and river slopes are often sowed with a plurality of varieties in order to cope with various environmental stresses such as pests, weather conditions, and soil conditions. The compound has a feature that there is little difference between varieties of turf in comparison with the cyclohexane derivative previously found by the present inventors.

In addition, by applying it to undergrowth such as an orchard or to pasture in a pasture, it is possible to suppress the growth and overgrowth of plants, reduce the number of cuttings, and facilitate cutting work. Furthermore, when applied to grass, it promotes the development of lateral buds and increases the density of lawn growth.

Next, the effect of the compound of the present invention will be specifically described with reference to test examples.

Test Example 1 (paddy rice growth inhibition test) The wettable powder of the compound of the present invention and the comparative compound chlormequat prepared according to Example 3 was used as the active ingredient in paddy rice (cultivar: Kinnanpu) in which the second leaf was completely developed. It was diluted with 1000 l of water per hectare so as to be 1 kg / ha and sprayed on the foliage.

After the fifth leaf was completely extracted, the foliage length of the fifth leaf was measured for 10 individuals per ward, and compared with the foliage length of the fifth leaf of the untreated plot, the inhibition rate (%) was obtained.

The suppression rate was rounded off to the nearest whole number.

The results are shown in Table 2.

Test Example 2 (Inhibitory effect on various types of turf) Four kinds of turfgrass seeds, Kentucky bluegrass, creeping red fuesque, pen cloth bentgrass, and perennial ryegrass, were sown in a 15 cm unglazed pot and grown. After cutting the plant height to 1 to 2 cm, the wettable powder of the compound of the present invention and the comparative compound prepared according to Example 3 was diluted with 1000 l of water per hectare so that the active ingredient was 1 kg / hectare, and sprayed on the foliage. Processed.

The plant height was measured 3 weeks after the chemical treatment, and the inhibition rate was calculated in comparison with the plant height of the untreated plot.

The suppression rate was rounded off to the nearest whole number.
At this time, the plant height of the untreated plots was 11 to 13 cm.

The results are shown in Table 3.

The results in Table 3 show that the compound of the present invention has an effect of suppressing the growth of plant height evenly with respect to each turfgrass as compared with the comparative compound, and is a general cultivating method for lawns in cold regions etc. Shows that it is particularly useful for reducing mowing work.

Test Example 3 (Rice Inhibition Test) The wettable powder of the compound of the present invention and the comparative compound chlormecote prepared in accordance with Example 3 was used as the active ingredient in the paddy rice (cultivar: Kinanpu) in which the second leaf was completely developed. It was diluted with 1000 l of water per hectare so as to be 1 kg / ha and sprayed on the foliage.

After the fifth leaf was completely extracted, the foliage length of the fifth leaf was measured for 10 individuals per ward, and compared with the foliage length of the fifth leaf of the untreated plot, the inhibition rate (%) was obtained.

The suppression rate was rounded off to the nearest whole number.

The results are shown in Table 4.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI Technical display location C07D 295/12 AZ 295/22 Z 307/52 307/68 333/20 333/38

Claims (2)

[Claims] 1. A general formula [Wherein R ¹ represents a hydrogen atom or a lower alkyl group, R ² represents a lower alkyl group, R ³ represents a hydrogen atom, an alkyl group, an alkenyl group, a hydroxyalkyl group, a cycloalkyl group, a morpholino group, an aminoalkyl group, N- alkylaminoalkyl group, N, N- dialkylaminoalkyl group, an alkoxycarbonylalkyl group, the formula - (CH ₂₎ lR ⁴ (wherein, R ⁴
Represents a lower alkoxy group, a lower alkylthio group, a benzylthio group, an anilino group, a morpholino group, a piperazino group, or a piperidino group which may be substituted with a lower alkyl group,
l represents an integer of 2 or 3. ),formula (Wherein X represents a halogen atom, a lower alkyl group, a lower alkoxy group, a phenoxy group or an alkoxycarbonylalkyloxy group, m represents an integer of 0 or 1, and n represents 0 to 2
Indicates an integer. ), The formula —CH ₂ R ⁵ (wherein R ⁵ is a furyl group,
A tenyl group or a pyridyl group is shown. ) Or expression (In the formula, R ⁵ has the same meaning as described above.). ] The cyclohexane derivative and its salt represented by these. 2. General formula [Wherein R ¹ represents a hydrogen atom or a lower alkyl group, R ² represents a lower alkyl group, R ³ represents a hydrogen atom, an alkyl group, an alkenyl group, a hydroxyalkyl group, a cycloalkyl group, a morpholino group, an aminoalkyl group, N- alkylaminoalkyl group, N, N- dialkylaminoalkyl group, an alkoxycarbonylalkyl group, the formula - (CH ₂₎ lR ⁴ (wherein, R ⁴
Represents a lower alkoxy group, a lower alkylthio group, a benzylthio group, an anilino group, a morpholino group, a piperazino group, or a piperidino group which may be substituted with a lower alkyl group,
l represents an integer of 2 or 3. ),formula (Wherein X represents a halogen atom, a lower alkyl group, a lower alkoxy group, a phenoxy group or an alkoxycarbonylalkyloxy group, m represents an integer of 0 or 1, and n represents 0 to 2
Indicates an integer. ), The formula —CH ₂ R ⁵ (wherein R ⁵ is a furyl group,
A tenyl group or a pyridyl group is shown. ) Or expression (In the formula, R ⁵ has the same meaning as described above.). ] The plant growth regulator containing the cyclohexane derivative and its salt represented by these as an active ingredient.