JP2013100266A - Plant growth regulator - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a specific inhibitor of brassinosteroid biosynthesis.SOLUTION: The plant growth regulator includes a compound represented by formula (I) (wherein, Rand Rdenote a hydrogen atom or the like; Rand Rdenote a phenyl group which may have a substituent or the like; Rdenotes a heteroaryl group including a nitrogen atom; X denotes a single bond or the like; and Y denotes an oxygen atom or the like) or its salt as an active constituent.

Description

  The present invention relates to a plant growth regulator comprising a compound having a brassinosteroid biosynthesis inhibitory action.

  Brassinosteroids have recently been recognized as a new class of plant hormones by combining molecular genetics and biosynthetic studies (Yokota, Trends in Plant Sci. 2, 137-143, 1997). Since the establishment of brassinosteroid chemistry, the biological activity of these congeners has been extensively studied: stem elongation, pollen tube growth, leaf bending, leaf opening, root suppression, proton pump activation (Mandava, Annu. Rev. Plant Physiol. Plant Mol. Biol. 39, pp. 23-52, 1988), promotion of ethylene production (Schlagnhaufer et al., Physiol. Plant, 61, pp. 555-558, 1984) , Differentiation of conduit elements (Iwasaki et al., Plant Cell Physiol. 32, pp. 1007-1014, 1991; Yamamoto et al., Plant Cell Physiol. 38, pp. 980-983, 1997), increased plant biomass production (Sakamoto et. Al., Nature Bioch. 24, pp105-109, 2005), cell elongation (Azpiroz et al., Plant Cell, 10, pp.219-230, 1998), expression of plant stress response function (Nakashita, H , et al, Plant J., 33, pp. 887-898, 2003), notable plant growth responses have been shown.

  In addition, extensive research on brassinosteroid biosynthesis has begun to elucidate the mechanism and regulation of its physiological action (Clouse, Plant J. 10, pp.1-8, 1996; Fujioka et al., Physiol. Plant , 100, pp.710-715, 1997). At present, more than 40 brassinosteroids have been identified, but most of the C28-branosteroids are very common plant sterols, and campesterols whose side chain carbon skeleton is the same as brassinolide It is thought to be biosynthesized from

  Several Arabidopsis mutants with specific dwarfing have been isolated and dwarf1 (dwf1: Feldman et al., Science, 243, pp.1351-1354, 1989; dim: Takahashi etal., Genes Dev., 9 pp. 97-107, 1995; cbb1: Kauschmann et al., Plant J., 9, pp. 701-703, 1996), structural photomorphogenesis and dwarfism (cpd; Szekeres et al., Cell, 85, pp.171-182, 1997), and deyellowing (det2: Li et al., Science, 272, pp.398-401, 1996; Fujioka et al., Plant Cell, 9, pp.1951-1962 , 1997). They are deficient in the brassinosteroid biosynthetic pathway. In addition, a pea dwarf mutant has been determined and reported to be brassinosteroid deficient (Nomura et al., Plant Physiol., 113, pp. 31-37, 1997). In these examples, it is known that the use of brassinolide counteracts the severe miniaturization of the mutant. These findings suggest that brassinosteroids have an essential role in plant growth and development, but biosynthetic inhibitors are more important than mutant analysis to elucidate the physiological importance of brassinolide. There is a need for other effective tools, including

  In general, a specific inhibitor of biosynthesis of an endogenous biologically active substance is very effective in understanding the physiological function of the endogenous substance, as seen in a method for studying the mechanism of action of an endogenous biologically active substance. Specific inhibitors of brassinosteroid biosynthesis are expected to provide new tools for understanding the function of brassinosteroids. Some substances that inhibit brassinosteroid biosynthesis have been known so far (Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4).

On the other hand, among the compounds included in the following formula (I), R ₁ and R ₂ are hydrogen atoms, R ₃ is a phenyl group, R ₄ is a 2,4-dichlorophenyl group, and R ₅ is A compound having a 1H-1,2,4-triazol-1-yl group, X being a single bond, and Y being an oxygen atom has been reported as a substance having a bactericidal action (Patent Document 5). However, the plant growth regulating action of this compound has not been known so far.

Japanese Patent Publication No. 2000-53657 Patent Publication 2001-247412 Japanese Patent Publication 2001-247413 Japanese Patent Publication 2001-247553 U.S. Pat.No. 4,338,327

  An object of the present invention is to provide a specific inhibitor of brassinosteroid biosynthesis.

  Several mutants lacking the biosynthetic enzyme gene are known in Arabidopsis thaliana, and the morphological changes are specific to brassinosteroid biosynthesis deficiency. In order to find an inhibitor, the present inventors eagerly searched for a compound that causes a morphological change peculiar to a brassinosteroid biosynthesis enzyme deficient strain. As a result, a 1- [4- (2-ethoxyphenoxymethyl) -2- (4-chlorophenyl- [1,3] dioxyl-2-ylmethyl) -1H- [1,2,4] triazole compound is desired. It was found to have an inhibitory effect.

That is, the present invention provides the following (1) to (8).
(1) The following formula (I):

(In the formula, R ₁ and R ₂ each independently represent a hydrogen atom or a lower alkyl group, R ₃ represents a phenyl group or naphthyl group which may have a substituent, and R ₄ may have a substituent. A phenyl group or a naphthyl group, R ₅ represents a heteroaryl group containing a nitrogen atom, X represents a single bond or —CH ₂ —, and Y represents an oxygen atom, a sulfur atom, NH or —CH ₂ —. The plant growth regulator containing the compound or its salt represented by this as an active ingredient.
(2) R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-chlorophenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2,4-triazol-1-yl The plant growth regulator according to (1), which is a group, X is a single bond, and Y is an oxygen atom.
(3) R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2,5-dichlorophenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2,4-triazole-1 The plant growth regulator according to (1), which is an -yl group, X is a single bond, and Y is an oxygen atom.
(4) R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-ethoxyphenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2,4-triazole-1- The plant growth regulator according to (1), which is an yl group, X is a single bond, and Y is an oxygen atom.
(5) R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-propoxyphenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2,4-triazole-1 The plant growth regulator according to (1), which is an -yl group, X is a single bond, and Y is an oxygen atom.
(6) R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-allyloxyphenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2,4-triazole-1 The plant growth regulator according to (1), which is an -yl group, X is a single bond, and Y is an oxygen atom.
(7) The plant growth regulator according to any one of (1) to (6), wherein the plant growth regulation is plant hatching, regulation of flowering time, induction of upright leaves, or weed control by reproduction control.
(8) A method for regulating plant growth, wherein the plant growth regulator according to any one of (1) to (7) is allowed to act on a plant.

  The compound of formula (I) or a salt thereof, which is an active ingredient of the plant growth regulator of the present invention, has a specific inhibitory action on brassinosteroid biosynthesis, for example, suppression of plant elongation, increase of plant biomass production It can be used as a plant growth regulator such as pollen growth inhibition, flower freshness preservation, plant anti-stress agent, weed control, plant aging inhibition, root hypertrophy.

It is the figure which showed the brassinosteroid biosynthesis inhibitory action of the compound 7b compared with the action of brassinazole (Brz). FIG. 5 is a diagram showing the effect of regulating the flowering time of compound 7b. FIG. 5 shows the growth regulating action of compound 7b. It is the figure which showed the growth control effect | action (induction of an upright leaf) with respect to rice of the compound 7b. It is the figure which showed the growth control effect | action (stalk hatching) with respect to rice of the compound 7b. It is the figure which showed the growth control effect | action with respect to turfgrass (pen cross) of the compound 7q. It is the figure which showed the growth control effect | action (growth suppression) with respect to turfgrass (pen cloth) of the compound 7q. In order from the left, control, 30 g ai / ha compound 7q treatment, 100 g ai / ha compound 7q treatment, and priomax treatment are shown.

  Hereinafter, the present invention will be described in detail.

In the above formula (I), as the lower alkyl group represented by R ₁ and R ₂ , a linear or branched alkyl group having about 1 to 6 carbon atoms can be used (an alkoxy having a lower alkyl moiety). The same applies to alkyl moieties such as groups.) For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group and the like can be mentioned.

R ₁ and R ₂ are preferably both hydrogen atoms.

Examples of the naphthyl group represented by R ₃ include a 1-naphthyl group and a 2-naphthyl group.

When the phenyl group or naphthyl group represented by R ₃ has a substituent, the type, number, or bonding position of the substituent is not particularly limited. For example, it preferably has 1 to 3, preferably 1 or 2 substituents, and when it has 2 or more substituents, they may be the same or different.

Examples of the substituent on the phenyl group or naphthyl group represented by R ₃ include a halogen atom (any of a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), a lower alkyl group (a methyl group, an ethyl group, n -Propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 3-methylbutyl group, etc.), lower alkenyl group (vinyl group, 1-propenyl group, allyl group (2 -Propenyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 3-methyl-2-butenyl group, etc.), lower cycloalkyl groups (cyclopropyl group, cyclobutyl group, cyclopentyl group, etc.), halogenated Lower alkyl group (such as trifluoromethyl group), lower alkoxy group (methoxy group, ethoxy group, n-propoxy group, isopropyloxy group, n-butoxy group, sec-butoxy group, tert- Toxyl group, 2-methylbutoxy group, 3-methylbutoxy group, etc.), lower alkenyloxy group (vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 3 -Methyl-2-butenyloxy group), lower cycloalkyloxy group (cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, etc.), amino group, mono- or dialkylamino group, carboxyl group, alkoxycarbonyl group (ethoxycarbonyl group) ), Alkanoyl group (such as acetyl group), aroyl group (such as benzoyl group), aralkyl group (such as benzyl group), aryl group (such as phenyl group), heteroaryl group (such as pyridyl group), heterocyclic group (pyrrolidinyl group) Etc.), hydroxyl group, nitro group, cyano group, etc. However, it is not limited to these. The substituent on the phenyl group is preferably a lower alkyl group, a halogen atom, a halogenated lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a halogenated lower alkoxy group, or a hydroxyl group, and more preferably a chlorine atom, a propoxy group, or an allyloxy group. preferable.

Examples of the substituted phenyl group represented by R ₃ include 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2, 6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluoro Phenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2-trifluoromethoxyphenyl group, 2-ethoxyphenyl group, 2 -Methoxyphenyl group, 2-methylphenyl group, 2-propoxyoxyphenyl group, 2-allyloxyphenyl group, 2-butoxyphenyl group, 2- (3-butenyloxy) phenyl group, 2-isobutoxypheny Group, 2-tert-butoxyphenyl group, 2-cyclopentyloxyphenyl group, 2- (3-methyl-2-butenyloxy) phenyl group, 2- (3-methylbutoxy) phenyl group, biphenyl-2-yl group, biphenyl A 4-yl group, a 2-allylphenyl group, a 2-benzylphenyl group, and the like can be given. Among these, 2-chlorophenyl group, 3-chlorophenyl group, 2,5-dichlorophenyl group, 2-fluorophenyl group, 2-ethoxyphenyl group, 2-methoxyphenyl group, 2-propoxyphenyl group, 2-allyloxy A phenyl group is preferable, and a 2-chlorophenyl group, a 2,5-dichlorophenyl group, a 2-ethoxyphenyl group, a 2-propoxyphenyl group, and a 2-allyloxyphenyl group are more preferable.

When the phenyl group or naphthyl group represented by R ₄ has a substituent, the type, number, or bonding position of the substituent is not particularly limited. For example, it preferably has 1 to 3, preferably 1 or 2 substituents, and when it has 2 or more substituents, they may be the same or different.

Examples of the substituent on the phenyl group or naphthyl group represented by R ₄ include a halogen atom (any of fluorine atom, chlorine atom, bromine atom or iodine atom), a lower alkyl group (methyl group, ethyl group, n -Propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 3-methylbutyl group, etc.), lower alkenyl group (vinyl group, 1-propenyl group, allyl group (2 -Propenyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 3-methyl-2-butenyl group, etc.), lower cycloalkyl groups (cyclopropyl group, cyclobutyl group, cyclopentyl group, etc.), halogenated Lower alkyl group (such as trifluoromethyl group), lower alkoxy group (methoxy group, ethoxy group, n-propoxy group, isopropyloxy group, n-butoxy group, sec-butoxy group, tert- Toxyl group, 2-methylbutoxy group, 3-methylbutoxy group, etc.), lower alkenyloxy group (vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 3 -Methyl-2-butenyloxy group), lower cycloalkyloxy group (cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, etc.), amino group, mono- or dialkylamino group, carboxyl group, alkoxycarbonyl group (ethoxycarbonyl group) ), Alkanoyl group (such as acetyl group), aroyl group (such as benzoyl group), aralkyl group (such as benzyl group), aryl group (such as phenyl group), heteroaryl group (such as pyridyl group), heterocyclic group (pyrrolidinyl group) Etc.), hydroxyl group, nitro group, cyano group, etc. However, it is not limited to these. The substituent on the phenyl group or naphthyl group is preferably a lower alkyl group, a halogen atom, a halogenated lower alkyl group, a lower alkoxy group, a halogenated lower alkoxy group or a hydroxyl group, more preferably a halogen atom or a halogenated lower alkyl group.

Examples of the naphthyl group represented by R ₄ include a 1-naphthyl group and a 2-naphthyl group.

Examples of the substituted phenyl group represented by R ₄ include a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and 3,4-dichlorophenyl. Group, 2,4-dichlorophenyl group, 3,4-difluorophenyl group, 2,4-difluorophenyl group, 4-bromophenyl group, 4-trifluoromethoxyphenyl group, 4-methylphenyl group, 4-trifluoromethyl Phenyl group, 3-trifluoromethylphenyl group, 4-hydroxyphenyl group, 4-methoxyphenyl group, 2-chloro-4-trifluoromethylphenyl group, 3-chloro-4-trifluoromethylphenyl group, 4-bromo -2-Chlorophenyl group, biphenyl group and the like can be mentioned. Of these, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-bromophenyl group, and 2-chloro-4-trifluoromethylphenyl group are preferable.

Examples of the heteroaryl group containing a nitrogen atom represented by R ₅ include 1H-1,2,4-triazol-1-yl group, 1H-imidazol-1-yl group, 4H-1,2,4-triazole-4- Yl group, 1H-pyrazol-1-yl group and the like. Of these, the 1H-1,2,4-triazol-1-yl group is preferred.

  X is preferably a single bond. The “single bond” means that an oxygen atom adjacent to X and a carbon atom are directly bonded in the formula (I).

  Y is preferably an oxygen atom.

  The compound represented by the above formula (I) may have one or more asymmetric carbons. In addition to optically active forms or diastereoisomers in a pure form based on asymmetric carbon, any mixture of isomers (for example, a mixture of two or more diastereoisomers) or racemates, etc. are all used for the plant growth of the present invention. It can be used as an active ingredient of a regulator. In addition, the compound represented by the formula (I) can form an acid addition salt, and may form an acid addition salt depending on the type of the substituent. The type of salt is not particularly limited, and salts with mineral acids such as hydrochloric acid and sulfuric acid, salts with organic acids such as p-toluenesulfonic acid, methanesulfonic acid and tartaric acid, metals such as sodium salt, potassium salt and calcium salt Examples thereof include salts with organic amines such as salts, ammonium salts and triethylamine, and salts with amino acids such as glycine.

  Specific examples of the compound represented by the formula (I) are shown in the following table, but the compounds usable for the plant growth regulator of the present invention are not limited thereto.

  Among the above compounds, preferred compounds are I-1 (Compound 7a), I-2 (Compound 7b), I-3 (Compound 7c), I-4 (Compound 7d), I-5 (Compound 7e), I -6 (compound 7f), I-7 (compound 7g), I-8 (compound 7h), I-9 (compound 7i), I-10 (compound 7j), I-11 (compound 7k), I-12 (Compound 7l), I-13 (Compound 7m), I-14 (Compound 7n), I-15 (Compound 7o), I-136 (Compound 7p), I-137 (Compound 7q) can be mentioned, More preferred compounds include I-2, I-7, I-13, I-136, and I-137.

The compounds represented by the above formula (I) can be suitably used according to the methods described in known literatures (for example, Tetrahedron Asymmetry, 14, pp. 3487-3493, 2003) or with reference to the descriptions thereof. Can be synthesized according to a method in which alterations or modifications are added. For example, in the above formula (I), R ₁ and R ₂ are hydrogen atoms, R ₃ is a phenyl group having a substituent R, R ₄ is a 4-chlorophenyl group, and R ₅ is 1H-1,2 , 4-Triazol-1-yl group, X is a single bond, and Y is an oxygen atom can be synthesized according to Scheme 1 below.

  The compound of the above formula (I) or a salt thereof, which is an active ingredient of the plant growth regulator of the present invention, has a specific inhibitory action on brassinosteroid biosynthesis. As used herein, the term “plant growth regulation” refers to, for example, plant hatching (extension suppression), regulation of flowering time, induction of upright leaves (and accompanying photosynthesis efficiency improvement, biomass increasing action), pollen It needs to be interpreted in the broadest sense including growth suppression, flower freshness preservation, plant anti-stress agents (heat, dryness, cold, etc.), weed control by reproductive control, plant aging suppression, root enlargement, etc. . For example, plant growth stimulants, plant growth inhibitors, herbicides and the like are typical examples of the plant growth regulator of the present invention, but the plant growth regulator of the present invention is not limited thereto. .

  The plant growth regulator of the present invention can be prepared as an agrochemical composition using, for example, pharmaceutical additives well known in the art. The form of the composition for agricultural chemicals is not particularly limited, and any form may be adopted as long as it is a form that can be used in the art. For example, a composition in the form of an emulsion, solution, oil, water solvent, wettable powder, flowable, powder, fine granule, granule, aerosol, fumigant, or paste can be used. A method for producing the composition for agricultural chemicals is not particularly limited, and any method available to those skilled in the art can be appropriately employed. As an active ingredient of the plant growth regulator of the present invention, two or more compounds represented by the above formula (I) or a salt thereof may be used in combination. Moreover, you may mix | blend the active ingredient of other agricultural chemicals, such as an insecticide, a fungicide, an insecticide fungicide, and a herbicide. The application method and application amount of the plant growth regulator of the present invention can be appropriately selected by those skilled in the art according to conditions such as application purpose, dosage form, and application location. A suitable application amount is about 0.1 to 1000 g as an active ingredient amount per 1 ha.

  The plant to which the plant growth regulator of the present invention is applied is not particularly limited as long as it is a plant that biosynthesizes brassinosteroid. Specific examples of the plant to be applied include dicotyledonous plants such as Arabidopsis thaliana, tomato and cucumber, and monocotyledonous plants such as rice, wheat, barley and corn, but are not limited thereto.

  Hereinafter, the present invention will be described more specifically with reference to examples. However, the scope of the present invention is not limited to the following examples.

[Example 1] Inhibition of Arabidopsis hypocotyl elongation The compounds represented by the following formula (Ia) (7a-z, 7aa-7ad), the compound (8a-h) represented by the formula (Ib), and Using the compound (9a-c) represented by the formula (Ic), an inhibitory effect on the elongation of the hypocotyl of Arabidopsis thaliana grown in the dark was examined.

The surface of the purchased Arabidopsis seeds was sterilized with 1% NaOCl solution for 20 minutes and washed 5 times with sterilized distilled water. The seeds were sown in 1% agarose solid medium (Agripot, Kirin Brew Co., Tokyo containing 0.5 × Murashige and Skoog salt, 1.5% sucrose). Plants were grown in dark conditions in a 22 ° C. growth chamber. The hypocotyl axis length of Arabidopsis thaliana when compound 7b is used is shown in FIG. In addition, Tables 6 to 10 show the structure and 50% inhibitory concentration (IC ₅₀ ) of each compound. IC ₅₀ was calculated assuming that the length of the hypocotyl of untreated Arabidopsis thaliana was 0% inhibition, and that the length of the hypocotyl of Arabidopsis thaliana was 0%. Data were collected from 15-20 seedlings and experiments were performed at least twice to establish reproducibility.

  As shown in FIG. 1 and Tables 6 to 10, the compounds represented by formula (Ia), formula (Ib), and formula (Ic) are the known brassinosteroid biosynthesis inhibitors, brassanazole (Brz). Higher inhibitory effect. In particular, the inhibitory effects of compounds 7m, 7p, and 7q were high.

[Example 2] Inhibition of plant hypocotyl elongation inhibition caused by treatment with an inhibitor with brassinolide Whether or not a test compound is a brassinosteroid biosynthesis inhibitor is considered to be an active substance of brassinosteroid. Whether the inhibitory effect is suppressed by the addition of brassinolide can be examined. Therefore, the inhibitory action of brassinolide on the inhibitory effect of the compounds represented by the above formulas (Ia), (Ib) and (Ic) was examined (Tables 11 to 15).

As shown in Tables 11 to 15, the Arabidopsis hypocotyl elongation inhibitory effect was suppressed by the addition of brassinolide (BL), but not by the addition of gibberellin (GA). This result confirmed that the compounds represented by formula (Ia), formula (Ib), and formula (Ic) specifically inhibited brassinosteroid biosynthesis.

[Example 3] Control of Arabidopsis flowering time Arabidopsis seeds are placed in a 10 cm square plastic pot, sown in a standard potting mix (1: 1 v / v promix: bellow sand), and irradiated with light. The cells were grown in a growth chamber at 22 ° C. with a period of 16 hours under conditions (2000 lux) and 8 hours under dark conditions. The drug treatment was performed by spraying uniformly on Arabidopsis thaliana in the 4-leaf stage at a dose of 4 to 400 g ai / ha. Thereafter, the growth of the plants was measured over time. The appearance of Arabidopsis treated with Compound 7b is shown in FIG. In addition, FIG. 3 shows the change over time in the diameter of Arabidopsis rosettes treated with Compound 7b.

  As shown in FIGS. 2 and 3, the growth of Arabidopsis treated with Compound 7b was suppressed. In addition, untreated Arabidopsis thaliana (Control) flowered on the 42nd day after germination, but Arabidopsis treated with compound 7b did not bloom.

[Example 4] Upright foliage of rice Akitakomachi seeds were grown in a growth chamber at a temperature of 30 ° C until reaching the third leaf stage at a light irradiation condition (5000 lux) for 16 hours and a dark condition of 8 hours. Transplanted into a cm square flooded plastic pot. The basic fertilizer was applied at N 5g / m2, P 8g / m2, and K 10g / m2. The chemical treatment was performed by adding to the flooded soil at a dose of 4 to 1000 g ai / ha. Subsequently, after growing under the same conditions, the leaf angle of rice was measured. The appearance of rice treated with compound 7b is shown in FIG.

  As shown in FIG. 4, the rice leaves treated with compound 7b were almost upright.

[Example 5] Hatching of rice Akitakomachi seeds selected with salt water at a specific gravity of 1.13 were grown until they became medium seedlings at the submerged seedling price and transplanted on May 17, 2011. The planting style was a square plant with a single plant, and the planting density was 60 plants per square meter. The basic fertilizer was applied at N 5g / square meter, P 8g / square meter, K 10g / square meter, and N 6g / square meter and K 5g / square meter were applied as additional fertilizer on July 18 of the same year. As a chemical treatment, the rice plants were sprayed at a dose of 4 to 1000 g ai / ha on July 21 of the same year. Thereafter, the growth of the plant was measured over time, and the appearance of the rice plant on August 20 is shown in FIG.

  As shown in FIG. 5, the growth of the stems of rice treated with compound 7b was suppressed.

Example 6 Inhibition of Golf Course Turfgrass Growth When commercially available pencloth seedlings were grown to 3 cm, Compound 7q was sprayed onto turfgrass at a dose of 30-100 g ai / ha. Thereafter, the growth of the plants was measured over time. FIG. 6 shows changes with time in the growth of turfgrass. As shown in the figure, in the untreated area, turfgrass growth was observed over time, and after about 2 months, the turfgrass grew to about 8.5 cm. In the Primomax treatment group, which is a gibberellin biosynthesis-inhibiting drug, the length of turfgrass was about 4.5 cm. On the other hand, in the 7q treatment section, it was found to be about 4.2 cm. The appearance of turfgrass is shown in FIG. As shown in FIG. 7, turfgrass growth was inhibited.

Synthesis Example 1 1-[[2- (4-Chlorophenyl) -4- (phenoxymethyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole (Compound 7a) Synthesis of

  Compound 7a is toluene-4-sulfonic acid 2- (4-chlorophenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester (tosylate 6) Prepared by reacting phenol (see Scheme 1). Tosylate 6 was prepared according to the following method.

Into a 50 ml eggplant flask was placed 0.88 g of 1- (4-chlorophenyl) -2-1H- [1,2,4] triazol-1-ylethanone (2) (4 mmol) and toluene (10 ml) was added. . 1 g of toluene-4-sulfonic acid 2,3-dihydroxypropyl ester (5) (4 mmol) and TfOH (1.5 ml) were added thereto and reacted at room temperature for 71 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was neutralized by adding a 5.8% aqueous sodium hydrogen carbonate solution (30 ml) (pH = 7). The resulting mixture was partitioned between ethyl acetate (30 ml × 3), the organic layer was collected, washed with saturated brine (30 ml), dried over sodium sulfate, and the solvent was evaporated under reduced pressure. In order to obtain crystals of the target compound, toluenesulfonate, the concentrated residue and 750 mg of p-toluenesulfonic acid (3.9 mmol) were dissolved in 10 ml of ethyl acetate, mixed and stirred for 30 minutes. Crystals are formed, filtered with suction, and recrystallized with acetonitrile to give the target compound toluene-4-sulfonic acid 2- (4-chlorophenyl) -2-1H- [1,2,4] triazole-1 -Ilmethyl- [1,3] dioxolan-4-ylmethyl ester (6) was obtained (yield 50.4%). ¹ H NMR (CD ₃ OD) δ 2.48 (s, 3H), 3.58 (dd, J = 5.9, 9.7 Hz, 1H), 3.72 (dd, J = 5.9, 9.7 Hz, 1H), 3.78-3.84 (m, 2H), 4.21-4.27 (m, 2H), 7.35 (s, 4H), 7.39 (d, J = 8.3 Hz, 2H), 7.79 (d, J = 8.3 Hz, 2H), 7.87 (s, 1H), 8.22 (s, 1H)

Compound 7a was prepared according to the following method. Potassium hydroxide (160 mg, 2.8 mmol) was added to tosylate 6 (485 mg, 0.78 mmol) and phenol (70 mg, 0.72 mmol) in dry DMF (5 mL), and the reaction mixture was stirred at 50 ° C. overnight. Heated. After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and EtOAc (20 mL) and the organic phase was separated. The aqueous phase was extracted with EtOAc (3 x 20 mL). Combine all organic layers, wash with brine (20 mL), dry over anhydrous sodium sulfate, filter, concentrate and purify by silica gel flash chromatography (EtOAc / hexanes = 1: 1) 7a was obtained (178.8 mg, yield 74.6%). mp 113.3-113.8 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.51 (dd, J = 5.9, 9.9 Hz, 1H), 3.73 (dd, J = 4.9, 9.7 Hz, 1H), 3.78 (dd, J = 5.1, 8.4 Hz, 1H), 3.83-3.86 (m, 1H), 4.28-4.33 (m, 1H), 4.48 (s, 2H), 6.77 (d, J = 7.7 Hz, 2H), 6.91 (t, J = 7.5 Hz, 1H), 7.21-7.25 (m, 2H), 7.31-7.33 (m, 2H), 7.39-7.41 (m, 2H), 7.89 (s, 1H), 8.30 (s, 1H) .HRMS -ESI calcd for C ₁₉ H ₁₈ ClN ₃ O ₃ Na [M + Na] ⁺ 394.0928, found 394.0891.

Synthesis Example 2 1-[[4-[(2-Chlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Synthesis of triazole (compound 7b)

The target compound 7b was obtained in the same manner as in Synthesis Example 1 using 2-chlorophenol instead of phenol (yield 24.3%). mp 117.6-119.3 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.87-3.92 (m, 1H), 3.94-9.98 (m, 2H), 4.41-4.47 (m, 1H), 4.50-4.58 (m, 2H), 6.82-6.84 (m, 1H), 6.91-6.95 (m, 1H), 7.20-7.24 (m, 1H), 7.33-7.38 (m, 3H), 7.42-7.45 (m, 2H), 7.90 ( s, 1H), 8.17 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₇ Cl ₂ N ₃ O ₃ Na [M + Na] ⁺ 428.0539, found 428.0496.

Synthesis Example 3 1-[[4-[(3-Chlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Synthesis of triazole (7c)

The target compound 7c was obtained in the same manner as in Synthesis Example 1 using 3-chlorophenol instead of phenol (yield 72.4%). mp 120.4-121.2 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.65 (dd, J = 5.3, 10 Hz, 1H), 3.77 (dd, J = 4.8, 9.9 Hz, 1H), 3.84 (dd, J = 5.5, 8.4 Hz, 1H), 3.90-3.95 (m, 1H), 4.33-4.39 (m, 1H), 4.58 (s, 2H), 6.74-6.76 (m, 1H), 6.82-6.84 (m, 1H ), 6.95-6.97 (m, 1H), 7.21-7.23 (m, 1H), 7.37-7.40 (m, 2H), 7.44-7.48 (m, 2H), 8.03 (s, 1H), 8.61 (s, 1H HRMS-ESI calcd for C ₁₉ H ₁₇ Cl ₂ N ₃ O ₃ Na [M + Na] ⁺ 428.0539, found 428.0496.

Synthesis Example 4 1-[[4-[(4-Chlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Synthesis of triazole (7d)

The target compound 7d was obtained in the same manner as in Synthesis Example 1 using 4-chlorophenol instead of phenol (yield 69.0%). mp 92.4-94.2 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.54 (dd, J = 5.5, 9.9 Hz, 1H), 3.72 (dd, J = 4.8, 9.5 Hz, 1H), 3.83 (dd, J = 4.9, 8.2 Hz, 1H), 3.89-3.92 (m, 1H), 4.33-4.39 (m, 1H), 4.55 (s, 2H), 6.77 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 7.39 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H), 7.97 (s, 1H), 8.40 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₇ Cl ₂ N ₃ O ₃ Na [M + Na] ⁺ 428.0539, found 428.0499.

Synthesis Example 5 1-[[4-[(2,3-Dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, Synthesis of 4-triazole (compound 7e)

The target compound 7e was obtained in the same manner as in Synthesis Example 1 using 2,3-dichlorophenol instead of phenol (yield 15.1%). mp 129.8-13.2 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.42-3.46 (m, 1H), 3.83-3.87 (m, 1H), 3.93-3.95 (m, 2H), 4.42-4.47 (m, 1H), 4.50-4.58 (m, 2H), 6.72-6.74 (m, 1H), 7.11-7.16 (m, 2H), 7.18-7.39 (m, 2H), 7.43-7.46 (m, 2H), 7.91 ( s, 1H), 8.17 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0105.

Synthesis Example 6 1-[[4-[(2,4-Dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, Synthesis of 4-triazole (compound 7f)

Using 2,4-dichlorophenol instead of phenol, the target compound 7f was obtained in the same manner as in Synthesis Example 1 (yield 32.2%). mp 122.1-124.8 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.44 (dd, J = 6.6, 9.5 Hz, 1H), 3.82 (dd, J = 4.6, 9.7 Hz, 1H), 3.92-3.94 (m , 2H), 4.41-4.44 (m, 1H), 4.53-4.54 (m, 2H), 6.75 (d, J = 8.8 Hz, 1H), 7.18-7.22 (m, 1H), 7.35-7.38 (m, 3H ), 7.43-7.45 (m, 2H), 7.90 (s, 1H), 8.16 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0106.

Synthesis Example 7 1-[[4-[(2,5-dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-triazole (compound 7g)

Using 2,5-dichlorophenol instead of phenol, 7 g of the target compound was obtained in the same manner as in Synthesis Example 1 (yield 33.4%). mp 167.0-168.3 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.76-3.88 (m, 4H), 4.36-4.39 (m, 1H), 4.52 (s, 2H), 6.86 (dd, J = 2.2, 8.4 Hz, 1H), 6.98 (d, J = 2.2 Hz, 1H), 7.24-7.27 (m, 3H), 7.31-7.33 (m, 2H), 7.58 (s, 1H), 8.13 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0106.

Synthesis Example 8 1-[[4-[(2,6-dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-Triazole (Compound 7h)

The target compound 7h was obtained in the same manner as in Synthesis Example 1 using 2,6-dichlorophenol instead of phenol (yield 33.1%). mp 102.7-104.8 ° C. ¹ H NMR (400 MHz, CD ₃ OD) δ 3.65 (dd, J = 5.9, 9.9 Hz, 1H), 3.84-3.89 (m, 2H), 4.38 (s, 1H), 4.52 ( s, 2H), 7.05-7.09 (m, 1H), 7.29-7.34 (m, 4H), 7.37-7.39 (m, 2H), 7.61 (s, 1H), 8.17 (s, 1H) .HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0106.

Synthesis Example 9 1-[[4-[(3,4-dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-Triazole (Compound 7i)

The target compound 7i was obtained in the same manner as in Synthesis Example 1 using 3,4-dichlorophenol instead of phenol (yield 23.8%). mp 112.2-113.6 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.47 (dd, J = 5.9, 9.5 Hz, 1H), 3.69 (dd, J = 5.1, 9.5 Hz, 1H), 3.79 (dd, J = 4.8, 8.4 Hz, 1H), 3.89 (dd, J = 6.6, 8.4 Hz, 1H), 4.32-4.37 (m, 1H), 4.52 (s, 2H), 6.69 (dd, J = 2.9, 8.8 Hz, 1H), 6.93 (d, J = 2.9 Hz, 1H), 7.33 (d, J = 8.8 Hz, 1H), 7.38-7.40 (m, 2H), 7.45-7.49 (m, 2H), 7.92 (s, 1H ), 8.18 (s, 1H). HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0104.

Synthesis Example 10 1-[[4-[(3,5-Dichlorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-Triazole (Compound 7j)

The target compound 7j was obtained in the same manner as in Synthesis Example 1 using 3,5-dichlorophenol instead of phenol (yield 28.9%). mp 109.4-112.1 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.49 (dd, J = 5.9, 8.8 Hz, 1H), 3.71 (dd, J = 5.3, 9.3 Hz, 1H), 3.78 (dd, J = 4.9, 8.6 Hz, 1H), 3.88-3.92 (m, 1H), 4.32-4.36 (m, 1H), 4.52 (s, 2H), 6.74-6.75 (m, 2H), 6.98-7.00 (m, 1H ), 7.39 (d, J = 8.8 Hz, 2H), 7.46 (d, J = 8.8 Hz, 2H), 7.93 (s, 1H), 8.18 (s, 1H) .HRMS-ESI calcd for C ₁₉ H ₁₆ Cl ₃ N ₃ O ₃ Na [M + Na] ⁺ 462.0149, found 462.0104.

Synthesis Example 11 1-[[4-[(2-Fluorophenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Triazole (Compound 7k)

The target compound 7k was obtained in the same manner as in Synthesis Example 1 using 2-fluorophenol instead of phenol (yield 48.5%). mp 97.8-99.7 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.51-3.55 (m, 1H), 3.83-3.94 (m, 3H), 4.40-4.44 (m, 1H), 4.53 (s, 2H) , 6.86-6.96 (m, 2H), 7.05-7.10 (m, 2H), 7.36-7.39 (m, 2H), 7.43-7.47 (m, 2H), 7.91 (s, 1H), 8.18 (s, 1H) HRMS-ESI calcd for C ₁₉ H ₁₇ ClFN ₃ O ₃ Na [M + Na] ⁺ 412.0834, found 412.0795.

Synthesis Example 12 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-triazole (compound 7l)

Using 2-trifluoromethoxyphenol instead of phenol, the target compound 7l was obtained in the same manner as in Synthesis Example 1 (yield 58.2%). mp 79.5-81.6 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.40-3.44 (m, 1H), 3.86-3.94 (m, 3H), 4.38-4.44 (m, 1H), 4.48-4.57 (m, 2H), 6.87-6.89 (m, 1H), 6.96-7.00 (m, 1H), 7.21-7.28 (m, 2H), 7.36-7.39 (m, 2H), 7.43-7.46 (m, 2H), 7.92 ( s, 1H), 8.17 (s, 1H). HRMS-ESI calcd for C ₂₀ H ₁₇ ClF ₃ N ₃ O ₄ Na [M + Na] ⁺ 478.0751, found 478.0705.

Synthesis Example 13 1-[[4-[(2-Ethoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Triazole (compound 7m)

The target compound 7m was obtained in the same manner as in Synthesis Example 1 using 2-ethoxyphenol instead of phenol (yield 51.8%). mp 104.6-105.9 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 1.37 (t, J = 7.0 Hz, 3H), 3.60-3.64 (m, 1H), 3.90-4.06 (m, 5H), 4.43-4.45 (m, 1H), 4.52-4.62 (m, 2H), 6.85-6.96 (m, 4H), 7.34-7.49 (m, 2H), 7.40-7.43 (m, 2H), 7.87 (s, 1H), 8.18 (s, 1H). HRMS-ESI calcd for C ₂₁ H ₂₂ ClN ₃ O ₄ Na [M + Na] ⁺ 438.1191, found 438.1149.

Synthesis Example 14 1-[[4-[(2-methoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Triazole (Compound 7n)

The target compound 7n was obtained in the same manner as in Synthesis Example 1 using 2-methoxyphenol instead of phenol (yield 52.9%). mp 121.9-124.1 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.54-3.58 (m, 1H), 3.82 (s, 3H), 3.86-3.95 (m, 3H), 4.43-4.46 (m, 1H) , 4.54 (s, 2H), 6.82-6.98 (m, 4H), 7.35-7.37 (m, 2H), 7.41-7.45 (m, 2H), 7.89 (s, 1 H), 8.19 (s, 1H). HRMS-ESI calcd for C ₂₀ H ₂₀ ClN ₃ O ₄ Na [M + Na] ⁺ 424.1034, found 424.0992.

Synthesis Example 15 1-[[4-[(2-methylphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Triazole (Compound 7o)

Using 2-methylphenol instead of phenol, the target compound 7o was obtained in the same manner as in Synthesis Example 1 (yield 69.3%). mp 112.6-114.5 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ 3.46 (m, 1H), 3.85-3.94 (m, 3H), 4.37-4.41 (m, 1H), 4.52 (s, 2H), 6.70 -6.72 (m, 1H), 6.86-6.90 (m, 1H), 7.11-7.17 (m, 2H), 7.36-7.39 (m, 2H), 7.43-7.46 (m, 2H), 7.91 (s, 1H) , 8.16 (s, 1H). HRMS-ESI calcd for C ₂₀ H ₂₀ ClN ₃ O ₃ Na [M + Na] ⁺ 408.1085, found 408.1051.

Synthesis Example 16 1-[[4-[(2-propioxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4 -Triazole (compound 7p)

Using 2-propoxyphenol instead of phenol, the target compound 7p was obtained in the same manner as in Synthesis Example 1 (yield 20.0%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.00 (t, J = 7.3 Hz, 3H), 1.74-1.80 (m, 2H), 3.61 (dd, J = 6.6, 9.9 Hz, 1H), 3.90-3.96 (m, 5H), 4.41-4.44 (m, 1H), 4.51-4.60 (m, 2H), 6.84-6.98 (m, 4H), 7.34-7.42 (m, 4H9, 7.87 (s, 1H), 8.17 ( The HRMS-ESI calculated for C ₂₂ H ₂₄ ClN ₃ O ₄ Na [M + Na] ⁺ was 452.1348, with 452.1352 found experimentally.

Synthesis Example 17 1-[[4-[(2-Allyloxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4 -Triazole (Compound 7q)

Using 2-allyloxyphenol instead of phenol, the target compound 7q was obtained in the same manner as in Synthesis Example 1 (yield 13.4%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.69 (dd, 1H, J = 6.2, 9.9 Hz, 1H), 3.90-3.99 (m, 3H), 3.97-3.99 (m, 2H), 4.42-4.48 ( m, 1H), 4.53-4.64 (m, 4H), 5.22-5.24 (m, 1H), 5.34-5.38 (m, 1H), 5.95-6.05 (m, 1H), 6.84-6.98 (m, 4H), 7.34-7.41 (m, 4H), 7.93 (s, 1H), 8.29 (s, 1H). The HRMS-ESI calculated for C ₂₂ H ₂₂ ClN ₃ O ₄ Na [M + Na] ⁺ was 450.1191, with 450.1195 found experimentally.

[Synthesis Example 18] 1-[[4-[(2-butoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4- Triazole (Compound 7r)

Using 2-butoxyphenol in place of phenol, the target compound 7r was obtained in the same manner as in Synthesis Example 1 (yield 40.4%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 0.93 (t, J = 7.5 Hz, 3H), 1.39-1.48 (m, 2H), 1.65-1.73 (m, 2H), 3.75 (dd, J = 5.7, 10.1 Hz, 1H), 3.90-4.04 (m, 5H), 4.42-4.47 (m, 1H), 4.54-4.70 (m, 2H), 6.84-6.98 (m, 4H), 7.33-7.40 (m, 4H) , 7.95 (s, 1H), 8.42 (s, 1H). The HRMS-ESI calculated for C ₂₃ H ₂₆ ClN ₃ O ₄ Na [M + Na] ⁺ was 466.1504, with 466.1509 found experimentally.

[Synthesis Example 19] 1-[[4-[(2- (3-butenyloxy) phenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1, 2,4-triazole (compound 7s)

Using 2- (3-butenyloxy) phenol instead of phenol, the target compound 7s was obtained in the same manner as in Synthesis Example 1 (yield 45.3%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 2.49 (q, J = 6.5 Hz, 2H), 3.90 (d, J = 4.0 Hz, 2H), 4.00-4.13 (m, 4H), 4.45-4.48 (m , 1H), 4.58-4.76 (m, 2H), 5.05-5.16 (m, 2H), 5.81-5.91 (m, 1H), 6.87-7.01 (m, 4H), 7.35-7.41 (m, 4H), 8.04 (s, 1H), 8.71 (s, 1H). The HRMS-ESI calculated for C ₂₃ H ₂₄ ClN ₃ O ₄ Na [M + Na] ⁺ was 464.1348, with 464.1351 found experimentally.

Synthesis Example 20 1-[[4-[(2-Isobutoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4 -Triazole (compound 7t)

Using 2-isobutoxyphenol instead of phenol, the target compound 7t was obtained in the same manner as in Synthesis Example 1 (yield 37.2%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.00 (dd, J = 4.6, 6.6 Hz, 6H), 2.00-2.10 (m, 1H), 3.66 (dd, J = 6.3, 10.0 Hz, 1H), 3.72 (d, J = 6.6Hz, 2H), 3.92-3.97 (m, 3H), 4.39-4.44 (m, 1H), 4.51-4.60 (m, 2H), 6.84-7.00 (m, 4H), 7.33-7.36 (m, 2H), 7.39-7.42 (m, 2H), 7.89 (s, 1H), 8.23 (s, 1H). The HRMS-ESI calculated for C ₂₃ H ₂₆ ClN ₃ O ₄ Na [M + Na] ⁺ was 466.1504, with 466.1509 found experimentally.

Synthesis Example 21 1-[[4-[(2-tert-butoxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-triazole (compound 7u)

Using 2-tert-butoxyphenol instead of phenol, the target compound 7u was obtained in the same manner as in Synthesis Example 1 (yield 14.5%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.32 (s, 9H), 3.60 (dd, J = 6.4, 9.7 Hz, 1H), 3.86-3.97 (m, 3H), 4.39-4.41 (m, 1H) The HRMS-ESI calculated for C ₂₃ , 4.51-4.61 (m, 2H), 6.82-7.06 (m, 4H), 7.35-7.43 (m, 4H), 7.97 (s, 1H), 8.32 (s, 1H). H ₂₆ ClN ₃ O ₄ Na [M + Na] ⁺ was 466.1504, with 466.1509 found experimentally.

Synthesis Example 22 1-[[4-[(2-Cyclopentyloxyphenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2,4 -Triazole (Compound 7v)

Using 2-cyclopentyloxyphenol instead of phenol, the target compound 7v was obtained in the same manner as in Synthesis Example 1 (yield 57.5%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.56-1.89 (m, 8H), 3.78 (dd, J = 5.7, 10.1 Hz, 1H), 3.90-3.93 (m, 1H), 3.99-4.07 (m, 2H), 4.42-4.47 (m, 1H), 4.55-4.77 (m, 3H), 6.88-6.98 (m, 4H), 7.34-7.40 (m, 4H), 7.97 (s, 1H), 8.45 (s, 1H). The HRMS-ESI calculated for C ₂₄ H ₂₆ ClN ₃ O ₄ Na [M + Na] ⁺ was 478.1504, with 478.1510 found experimentally.

Synthesis Example 23 1-[[4-[(2- (3-Methyl-2-butenyloxy) phenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl]- 1H-1,2,4-triazole (Compound 7w)

Using 2- (3-methyl-2-butenyloxy) phenol instead of phenol, the target compound 7w was obtained in the same manner as in Synthesis Example 1 (yield 47.9%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.67 (s, 3H), 1.71 (s, 3H), 3.68-3.73 (m, 1H), 3.92-4.00 (m, 3H), 4.42-4.65 (m, 5H), 5.38-5.41 (m, 1H), 6.85-6.95 (m, 4H), 7.32-7.39 (m, 4H), 7.88 (s, 1H), 8.25 (s, 1H). The HRMS-ESI calculated for C ₂₄ H ₂₆ ClN ₃ O ₄ Na [M + Na] ⁺ was 478.1504, with 478.1510 found experimentally.

Synthesis Example 24 1-[[4-[(2- (3-Methylbutoxy) phenoxy) methyl] -2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1 , 2,4-Triazole (Compound 7x)

Using 2- (3-methylsibutoxy) phenol instead of phenol, the target compound 7x was obtained in the same manner as in Synthesis Example 1 (yield 37.2%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 0.92 (d, J = 3.3 Hz, 3H), 0.94 (d, J = 3.3 Hz, 3H), 1.54-1.65 (m, 2H), 1.73-1.80 (m , 1H), 3.84 (dd, J = 3.8, 10.1 Hz, 1H), 3.91-3.95 (m, 1H), 3.98-4.09 (m, 4H), 4.44-4.50 (m, 1H), 4.57-4.76 (m , 2H), 6.86-7.00 (m, 4H), 7.35-7.40 (m, 4H), 8.01 (s, 1H), 8.60 (s, 1H). The HRMS-ESI calculated for C ₂₄ H ₂₈ ClN ₃ O ₄ Na [M + Na] ⁺ was 480.1661, with 480.1665 found experimentally.

Synthesis Example 25 1-[[4-[(biphenyl-2-yloxymethyl)]-2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-triazole (compound 7y)

The target compound 7y was obtained in the same manner as in Synthesis Example 1 using 2-phenylphenol instead of phenol (yield 7.3%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.57-3.61 (m, 1H), 3.72-3.75 (m, 1H), 3.80-3.83 (m, 1H), 3.88-3.92 (m, 1H), 4.25- 4.28 (m, 1H), 4.34 (s, 2H), 6.91 (d, J = 8.3 Hz, 1H), 7.06-7.10 (m, 1H), 7.23-7.38 (m, 9H), 7.44-7.47 (m, 2H), 7.86 (s, 1H), 8.08 (s, 1H). The HRMS-ESI calculated for C ₂₅ H ₂₂ ClN ₃ O ₃ Na [M + Na] ⁺ was 470.1242, with 470.1250 found experimentally.

Synthesis Example 26 1-[[4-[(biphenyl-4-yloxymethyl)]-2- (4-chlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2, 4-triazole (compound 7z)

The target compound 7z was obtained in the same manner as in Synthesis Example 1 using 4-phenylphenol instead of phenol (yield 20.8%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.56 (dd, J = 6.2, 9.8Hz, 1H), 3.82-3.86 (m, 2H), 3.90-3.94 (m, 1H), 4.36-4.41 (m, 1H), 4.53 (s, 2H), 6.89-6.92 (m, 2H), 7.29-7.33 (m, 1H), 7.37-7.44 (m, 4H), 7.46-7.56 (m, 6H), 7.92 (s, 1H), 8.21 (s, 1H). The HRMS-ESI calculated for C ₂₅ H ₂₂ ClN ₃ O ₃ Na [M + Na] ⁺ was 470.1242, with 470.1249 found experimentally.

Synthesis Example 27 1- [2- (4-Chlorophenyl) -4- (naphthalen-1-yloxymethyl)-[1,3] -dioxolan-2-ylmethyl] -1H- [1,2,4] -Triazole (Compound 7aa)

The target compound 7aa was obtained in the same manner as in Synthesis Example 1 using 1-naphthanol instead of phenol (yield 13.9%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.76 (dd, J = 6.2, 9.6 Hz, 1H), 3.98-4.06 (m, 3H), 4.51-4.57 (m, 3H), 6.73-6.75 (m, 1H), 7.36-7.42 (m, 3H), 7.45-7.52 (m, 5H), 7.78-7.82 (m, 1H), 7.94 (s, 1H), 8.11-8.13 (m, 1H), 8.31 (s, 1H). The HRMS-ESI calculated for C ₂₃ H ₂₀ ClN ₃ O ₃ Na [M + Na] ⁺ was 444.1085, with 444.1091 found experimentally.

Synthesis Example 28 1- [2- (4-Chlorophenyl) -4- (naphthalen-2-yloxymethyl)-[1,3] -dioxolan-2-ylmethyl] -1H- [1,2,4] -Triazole (compound 7ab)

The target compound 7ab was obtained in the same manner as in Synthesis Example 1 except that 2-naphthanol was used in place of phenol (yield 42.5%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.72 (dd, J = 5.8, 10.0 Hz, 1H), 3.85-3.97 (m, 3H), 4.42-4.45 (m, 1H), 4.56 (s, 2H) , 7.05 (d, J = 2.5 Hz, 1H), 7.12 (dd, J = 2.5, 9.0 Hz, 1H), 7.33-7.41 (m, 3H), 7.43-7.50 (m, 3H), 7.74-7.78 (m , 3H), 7.95 (s, 1H), 8.31 (s, 1H). The HRMS-ESI calculated for C ₂₃ H ₂₀ ClN ₃ O ₃ Na [M + Na] ⁺ was 444.1085, with 444.1092 found experimentally.

Synthesis Example 29 1- [4- (2-Allylphenoxymethyl) -2- (4-chlorophenyl)-[1,3] -dioxolan-2-ylmethyl] -1H- [1,2,4] -triazole (Compound 7ac)

Using 2-allylphenol instead of phenol, the target compound 7ac was obtained in the same manner as in Synthesis Example 1 (yield 45.7%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.31 (d, J = 6.7 Hz, 2H), 3.50 (dd, J = 6.7, 9.8 Hz, 1H), 3.85-3.96 (m, 3H), 4.37-4.40 (m, 1H), 4.53 (s, 2H), 4.96-5.02 (m, 2H), 5.87-5.97 (m, 1H), 6.74 (d, J = 6.7 Hz, 1H), 6.91-6.95 (m, 1H ), 7.12-7.22 (m, 1H), 7.36-7.39 (m, 2H), 7.42-7.45 (m, 2H), 7.93 (s, 1H), 8.24 (s, 1H). The HRMS-ESI calculated for C ₂₂ H ₂₂ ClN ₃ O ₃ Na [M + Na] ⁺ was 434.1242, with 434.1248 found experimentally.

Synthesis Example 30 1- [4- (2-Benzylphenoxymethyl) -2- (4-chlorophenyl)-[1,3] -dioxolan-2-ylmethyl] -1H- [1,2,4] -triazole (Compound 7ad)

Using 2-benzylphenol instead of phenol, the target compound 7ad was obtained in the same manner as in Synthesis Example 1 (yield 42.4%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.40 (dd, J = 6.9, 9.4 Hz, 1H), 3.56-3.59 (m, 1H), 3.71-3.81 (m, 2H), 3.87-3.96 (m, 2H), 4.23-4.29 (m, 1H), 4.45 (d, J = 3.7 Hz, 2H), 6.73 (d, J = 8.0 Hz, 1H), 6.91-6.95 (m, 1H), 7.10-7.15 (m , 4H), 7.19-7.23 (m, 3H), 7.35-7.42 (m, 4H), 7.91 (s, 1H), 8.10 (s, 1H). The HRMS-ESI calculated for C ₂₆ H ₂₄ ClN ₃ O ₃ Na [M + Na] ⁺ was 484.1398, with 484.1404 found experimentally.

[Synthesis Example 31] 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2-phenyl-1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole ( Compound 8a)

  Compound 8a consists of 2-trifluorophenol and toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester (tosylate) Prepared by reacting with 6a). Tosylate 6a was prepared according to the following method.

  DMF (12 ml) was added to a 500 ml three-necked flask, and 8.14 g of triazole (0.12 mol) was dissolved while cooling with ice. 5.9 g of triethylamine (0.06 mol) was added dropwise thereto and stirred for 30 minutes, and then 12 g of 2-bromo-acetophenone (0.06 mol) was added while stirring little by little with a spoonful and allowed to react for 17 hours. After completion of the reaction, 500 ml of ethyl acetate was added to the reaction mixture and cooled on ice for 30 minutes. The precipitated crystals were removed by suction filtration, and the filtrate was partitioned with distilled water (200 ml × 3), and the aqueous layer was partitioned with ethyl acetate (200 ml × 3). The organic layer was collected, washed with saturated brine (30 ml), dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Dissolve the concentrated residue in 20 ml of a solution of ethyl acetate: methanol (1: 1) and use a silica gel column with a column bed volume of 200 ml (height 10 cm) to obtain the target compound with ethyl acetate: methanol (1: 1). Was eluted. The solvent was distilled off under reduced pressure and recrystallized using ethyl acetate and hexane. The target compound 1-phenyl-2-1H- [1,2,4] triazol-1-yl-ethanone (2a) was obtained. Next, tosylate 6a was prepared by reacting 2a with toluene-4-sulfonic acid 2,3-dihydroxypropyl ester according to the synthesis method of tosylate 6 of Synthesis Example 1. Compound 8a was prepared from the obtained tosylate 6a and 2-trifluorophenol according to the method of Synthesis Example 1 (yield: 58.9%). δ 3.34-3.38 (m, 1H), 3.86-3.95 (m, 3H), 4.40-4.44 (m, 1H), 4.51-4.60 (m, 2H), 6.87-6.89 (m, 1H), 6.95-7.00 ( m, 1H), 7.21-7.28 (m, 2H), 7.40-7.44 (m, 3H), 7.51-7.54 (m, 2H), 7.93 (s, 1H), 8.17 (s, 1H)

Synthesis Example 32 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2- (4-methylphenyl) -1,3-dioxolan-2-yl] methyl] -1H-1,2 , 4-Triazole (Compound 8b)

  Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2- ( 4-methylphenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester was used to produce the desired compound 8b in the same manner as in Synthesis Example 31. Obtained (yield: 69.6%). δ 2.37 (s, 3H), 3.33-3.37 (m, 1H), 3.84-3.94 (m, 3H), 4.37-4.43 (m, 1H), 4,49-4.57 (m, 2H), 6.86-6.89 ( m, 1H), 6.95-6.99 (m, 1H), 7.20-7.28 (m, 4H), 7.38-7.41 (m, 2H), 7.93 (s, 1H), 8.16 (s, 1H)

Synthesis Example 33 1- [2-Biphenyl-4-yl-4- (2-trifluoromethoxyphenoxymethyl)-[1,3] dioxolan-2-ylmethyl] -1H- [1,2,4] triazole (Compound 8c)

  Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2-biphenyl Using 4--4-yl-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester, the target compound 8c was obtained in the same manner as in Synthesis Example 31. (Yield: 30.6%). δ 3.35-3.40 (m, 1H), 3.87-3.91 (m, 2H), 3.96-4.00 (m, 1H), 4.44-4.48 (m, 1H), 4.55-4.64 (m, 2H), 6.88-6.91 ( m, 1H), 6.96-7.00 (m, 1H), 7.21-7.29 (m, 2H), 7.36-7.40 (m, 1H), 7.45-7.48 (m, 2H), 7.58-7.64 (m, 6H), 7.95 (s, 1H), 8.21 (s, 1H)

Synthesis Example 34 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2- (4-trifluoromethylphenyl) -1,3-dioxolan-2-yl] methyl] -1H-1 , 2,4-Triazole (Compound 8d)

  Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2- ( 4-trifluoromethylphenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester and the target compound in the same manner as in Synthesis Example 16. 8d was obtained (yield: 28.2%). δ 3.43-3.48 (m, 1H), 3.83-3.93 (m, 3H), 4.41-4.45 (m, 1H), 4.51-4.60 (m, 2H), 6.88-6.90 (m, 1H), 6.97-7.02 ( m, 1H), 7.22-7.29 (m, 2H), 7.63-7.68 (m, 4H), 7.92 (s, 1H), 8.19 (s, 1H)

Synthesis Example 35 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1, 2,4-Triazole (Compound 8e)

  Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2- ( 2,4-Dichlorophenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester and the target compound 8e in the same manner as in Synthesis Example 31 (Yield: 43.6%) was obtained. δ 3.42-3.46 (m, 1H), 3.82-3.98 (m, 3H), 4.40-4.46 (m, 1H), 4.75-4.88 (m, 2H), 6.88-6.90 (m, 1H), 6.96-7.02 ( m, 1H), 7.22-7.29 (m, 3H), 7.47-7.55 (m, 2H), 7.90 (s, 1H), 8.19 (s, 1H)

Synthesis Example 36 1-[[4-[(2-trifluoromethoxyphenoxy) methyl] -2- (3,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-1, 2,4-Triazole (Compound 8f)

  Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2- ( 3,4-Dichlorophenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester and the target compound 8f in the same manner as in Synthesis Example 31 (Yield: 42.7%) δ 3.43-3.47 (m, 1H), 3.86-3.96 (m, 3H), 4.40-4.46 (m, 1H), 4.48-4.57 (m, 2H), 6.87 -6.90 (m, 1H), 6.97-7.01 (m, 1H), 7.22-7.33 (m, 3H), 7.46-7.48 (m, 1H), 7.60-7.61 (m, 1H), 7.92 (s, 1H) , 8.18 (s, 1H)

Synthesis Example 37 1- [2-Naphthalen-2-yl-4- (2-trifluoromethoxyphenoxymethyl)-[1,3] dioxolan-2-ylmethyl] -1H- [1,2,4] triazole (Compound 8g)

Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2-naphthalene -2-yl-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester was used in the same manner as in Synthesis Example 31 to obtain 8 g of the desired compound. (Yield: 42.6%). δ 3.39-3.43 (m, 1H), 3.88-3.99 (m, 3H), 4.47-4.48 (m, 1H), 4.59-4.68 (m, 2H), 6.89-7.02 (m, 2H), 7.21-7.28 ( m, 2H), 7.51-7.61 (m, 3H), 7.85-8.02 (m, 5H), 8.21 (s, 1H)

Synthesis Example 38 1- [2- (4-Fluorophenyl) -4- (2-trifluoromethoxyphenoxymethyl)-[1,3] -dioxolan-2-ylmethyl] -1H- [1,2,4 ] -Triazole (Compound 8h)

Toluene-4-sulfonic acid 2-phenyl-2-2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester instead of toluene-4-sulfonic acid 2- ( 4-Fluorophenyl) -2-1H- [1,2,4] triazol-1-ylmethyl- [1,3] dioxolan-4-ylmethyl ester was used to produce the target compound 8h in the same manner as in Synthesis Example 31. Obtained (yield: 31.6%). mp. = 60.8-62.5 ° C. ¹ H NMR (400 MHz, CDCl ₃ ) δ: 3.40 (dd, J = 7.1, 9.3 Hz, 1H), 3.86-3.94 (m, 3H), 4.39-4.43 (m, 1H), 4.53 (d, J = 5.1 Hz, 2H), 6.87-6.89 (m, 1H), 6.96-7.05 (m, 1H), 7.06-7.10 (m, 2H), 7.21-7.28 (m, 2H), 7.46-7.50 (m, 2H) , 7.91 (s, 1H), 8.16 (s, 1H). The HRMS-ESI calculated for C ₂₀ H ₁₇ F ₄ N ₃ O ₄ Na [M + Na] ⁺ was 462.1047, with 462.0999 found experimentally.

Synthesis Example 39 1- [2- (4-Chlorophenyl) -4- (2-ethoxyphenoxymethyl)-[1,3] -dioxolan-2-ylmethyl] -1H-imidazole (Compound 9a)

Instead of 1- (4-chlorophenyl) -2-1H- [1,2,4] triazol-1-ylethanone, 1- (4-chlorophenyl) -2-imidazol-1-ylethanone was used. Instead, using 2-ethoxyphenol, the target compound 9a was obtained in the same manner as in Synthesis Example 1 (yield: 16.6%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.38 (t, J = 7.0 Hz, 3H), 3.52 (dd, J = 6.5, 10.0 Hz, 1H), 3.84-3.93 (m, 3H), 4.00-4.06 (m, 2H), 4.14-4.25 (m, 2H), 4.38-4.44 (m, 1H), 6.83-6.97 (m, 6H), 7.29-7.42 (m, 5H). The HRMS-ESI calculated for C ₂₂ H ₂₃ ClN ₂ O ₄ Na [M + Na] ⁺ was 437.1239, with 437.1238 found experimentally.

Synthesis Example 40 1- [2- (4-Chlorophenyl) -4- (2-ethoxyphenoxymethyl)-[1,3] -dioxolan-2-ylmethyl] -4H- [1,2,4] -triazole (Compound 9b)

Instead of 1- (4-chlorophenyl) -2-1H- [1,2,4] triazol-1-ylethanone, 1- (4-chlorophenyl) -2-4H- [1,2,4] triazole-1 -The target compound 9b was obtained in the same manner as in Synthesis Example 1 using yl ethanone and 2-ethoxyphenol instead of phenol (yield: 16.9%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.37 (t, J = 8.5 Hz, 3H), 3.66 (dd, J = 6.0, 10.1 Hz, 1H), 3.87-3.92 (m, 2H), 3.96-4.06 (m, 3H), 4.23-4.38 (m, 2H), 4.41-4.47 (m, 1H), 6.85-6.98 (m, 4H), 7.35-7.40 (m, 4H), 8.10 (s, 2H).

Synthesis Example 41 1- [2- (4-Chlorophenyl) -4- (2-ethoxyphenoxymethyl)-[1,3] -dioxolan-2-ylmethyl] -1H-pyrazole (Compound 9c)

Instead of 1- (4-chlorophenyl) -2-1H- [1,2,4] triazol-1-ylethanone, 1- (4-chlorophenyl) -2-pyrazol-1-ylethanone was used, Instead, using 2-ethoxyphenol, the target compound 9c was obtained in the same manner as in Synthesis Example 1 (yield: 69.9%). ¹ H NMR (400 MHz, CDCl ₃ ) δ: 1.34 (t, J = 7.0 Hz, 3H), 3.71-3.79 (m, 2H), 3.88-4.02 (m, 4H), 4.23-4.29 (m, 1H) , 4.41 (s, 2H), 6.25 (t, J = 2.1 Hz, 1H), 6.76-6.93 (m, 4H), 7.27-7.30 (m, 2H), 7.39-7.42 (m, 2H), 7.46-7.50 (m, 2H).

  The plant growth regulator of the present invention is useful for suppressing plant elongation, increasing plant biomass production, suppressing pollen growth, maintaining flower freshness, plant antistress agents, weed control, plant aging suppression, root enlargement, etc. It can be used in the agricultural field.

Claims (8)

Formula (I) below:
(In the formula, R ₁ and R ₂ each independently represent a hydrogen atom or a lower alkyl group, R ₃ represents a phenyl group or naphthyl group which may have a substituent, and R ₄ may have a substituent. A phenyl group or a naphthyl group, R ₅ represents a heteroaryl group containing a nitrogen atom, X represents a single bond or —CH ₂ —, and Y represents an oxygen atom, a sulfur atom, NH or —CH ₂ —. The plant growth regulator containing the compound or its salt represented by this as an active ingredient. R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-chlorophenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is a 1H-1,2,4-triazol-1-yl group The plant growth regulator according to claim 1, wherein X is a single bond and Y is an oxygen atom. R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2,5-dichlorophenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is a 1H-1,2,4-triazol-1-yl group The plant growth regulator according to claim 1, wherein X is a single bond, and Y is an oxygen atom. R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-ethoxyphenyl group, R ₄ is a 4-chlorophenyl group, R ₅ is a 1H-1,2,4-triazol-1-yl group The plant growth regulator according to claim 1, wherein X is a single bond and Y is an oxygen atom. R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-propoxyphenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is a 1H-1,2,4-triazol-1-yl group The plant growth regulator according to claim 1, wherein X is a single bond, and Y is an oxygen atom. R ₁ and R ₂ are hydrogen atoms, R ₃ is a 2-allyloxyphenyl group, R ₄ is a 4-chlorophenyl group, and R ₅ is a 1H-1,2,4-triazol-1-yl group The plant growth regulator according to claim 1, wherein X is a single bond, and Y is an oxygen atom.   The plant growth regulator according to any one of claims 1 to 6, wherein the plant growth regulation is plant hatching, regulation of flowering time, induction of upright leaves, or weed control by reproduction control.   A method for controlling plant growth, wherein the plant growth regulator according to any one of claims 1 to 7 is allowed to act on a plant.