JPS6239581A - Triazole derivative, its production and plant growth regulating composition containing said derivative - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides heterocyclic compounds useful as plant growth regulators,
The present invention relates to a method for producing the same and a plant growth control composition containing the same.

European Patent Application Publication No. 2003-02-2121 describes in detail the use of certain triazole and imidazole compounds. It has also been stated that these compounds are useful for plant growth regulation, but no detailed test results regarding this effect have been presented.

The present inventors have recently discovered the above-mentioned European patent publication oor2a col.
Among the wide range of compounds disclosed in the publication, certain triazole compounds have been found to have unexpected, robust and surprisingly excellent plant growth regulation properties.

Therefore, according to the present invention, general formula (I): [wherein R1 is an alkyl group having a carbon number of μ to 9, a haloargyl group having a carbon number of 3 to lr@ll, or a group -C)I2
-CH2-Z (Z is a cycloalkyl ring or a cycloalkenyl ring containing 3 to 4 carbon atoms and optionally substituted); R2 is hydrogen; Or carbon number 7~
triazole derivatives and stereoisomers thereof; and salts, esters and metal complexes thereof; be done.

The triazole derivatives of the invention may contain asymmetric centers.

Such compounds are usually obtained in the form of racemic mixtures.

However, these racemic mixtures and other mixtures can be resolved into the individual isomers using conventional methods, and these n-isomers are also encompassed by the present invention.

A preferred group R2 is hydrogen and fc is a methyl group.

Hydrogen is preferred for pestles.

R1 can be a branched chain or a straight chain argyl group, and fc can be a straight alkyl group with a carbon number of tt to 7; or a branched chain with a carbon number of tt to 7; or a branched chain with a carbon number of 3 to tm; A straight chain haloalkyl group is preferred. When R is a haloalkyl group - this group preferably contains one halogen atom. Preferred halogen atoms are chlorine, bromine and fluorine, especially chlorine.

When R is -CH20H2-Z, examples of group 2 include cyclopropyl, cyclobutyl, cyclopentyl,
Mention may be made of cyclohexyl, cyclopentenyl and cyclohexenyl groups. The group 2+1 is preferably substituted with, for example, a lower alkyl group (for example, an alkyl group having 1 to tt carbon atoms) or a halogen, but is not monosubstituted.

R6 is /11 depending on the case! Preferably, it is a tertiary-butyl group substituted with a halogen atom. Preferred A halogen atoms are fluorine, chlorine and bromine, and chlorine for ¥P.

The present invention includes all salts, esters and metal complexes of compounds of general formula +1+ where R2 is hydrogen.

Examples of esters include acetate, benzoate, and acetate. Examples of salts include toluenesulfone m-salt, p-decylbenzenesulfonate, hydrochloride, hydrobromide and orthophosphate. Without limiting General a of the above description, the present invention also includes compounds that decompose in agricultural and chemical applications to yield compound #n of general formula +11.

Examples of the compounds of the present invention are shown in Table 1 below: In Table 1, various groups represented by R1 and R2 are shown in addition to the general formula m, and 85 in the same table is as follows. is a group having the structure: H6 -CH,X CH3 (wherein X is shown in Table 1).

Examples of salts of f and λ in Table 1 are shown in Table 2; in Table 2, the ninth acid from which the salt is derived is shown in 1a.

12C, HCZ 1tttt-/
ryjD, HBr hygroscopic solid uE, l (, PO4 low melting point solid general formula fill: (Jff &) (llb) (wherein R1 and R3 have the above meanings M), respectively, a compound 1L of the general formula (iVa) or (■b) two RM
(■a) An organometallic compound represented by R'M (lt/b) (wherein R1 and R3 have the above-mentioned meanings and 1M is a metal, preferably lithium, magnesium, titanium or zirconium); It can be produced by reacting. The reaction, ethyl ether, tetrahydroalane, etc., takes place conveniently in a solvent such as dichloromethane under an inert atmosphere at a temperature varying from -10 DEG to +10 DEG C. The reaction product E51 is isolated by co-quenching with a proton donor (qu@nch).

When M is magnesium, the organometallic compound is more specifically RMg halogen and tBuMg halogen. When M is titanium, the organometallic compound is more specifically RTi(killed to 0-7)6
4 liters is tBuTi (0-alkyl)3. , when M is zirconium, the organometallic compound is more specifically RZr(0-alkyl)5 or tBu
Al in Zr (0-alkyl).

The compound of the general formula (I) is -Mayu, the general formula M or (■
): (V) (VL) (in the formula,
R1 and R6 have the meanings given above and Hal is halogen, preferably chlorine or bromine)
．． The reaction with triazole in the presence of an acid binding agent (e.g. potassium carbonate) is carried out in a convenient solvent by 1. It can be prepared by reacting co-, g-trilinozole in the form of one of its alkali metal salts.

The present inventor has discovered that a compound of general formula (V'l or (Vl)) and 1
．． 2,1t-) IJ azole is reacted with the l-substituted triazole in the presence of an acid binder such as potassium carbonate in a solvent such as methylformamide, containing the l-substituted triazole as the main component and converting the l- Toriryozol has low tFN,
It was observed that a mixture existing as a fraction was formed. This mixture may be used without isolating the regioisomer, but if desired the isomer can be easily separated, for example by fractional crystallization or vacuum distillation. On the contrary, the present inventors have found that the general formula Mma9 is mainly unsubstituted triazole is formed by reaction with an alkali metal salt of (■) [Hymonide and /, j, tt-), lJ azole] Recognize your friend.

Therefore, when it is desired to produce only l-substituted triazoles, the compound of general formula (■) and the sodium salt of -2,g-) lyazole can be combined for 20~
The reaction can be carried out at 120°C. The salt may be dissolved in a convenient solvent such as acetonitrile, methanol, ethanol or polymethylformaldehyde (2 g).
+ Sodium hydride to 17azole or 7t to sodium methoxy? It can be prepared by adding a knife. The raw product may be isolated by pouring the reaction mixture into water and extracting the product with a suitable organic solution such as diethyl ether, ethyl acetate or dichloromethane.

The ethers (when R2 is alkyl) and esters of the present invention are obtained by reacting this compound with a suitable halide, acid chloride, or acid anhydride in the presence of a suitable base. It can be manufactured by

The compound of the general formula (■) is a compound of the general formula (■): (wherein R1 and R6 have the above-mentioned meanings) and a dimethylsulfonium methi-y? CJkCB,
llt, 3712 (iql, 2') reference] Is it dimethylsulfoxonium? CJAC'3. lr7
．． /3!3 (/9tj)] using the method described in the above-mentioned literature.

Ketone compound #lJ of general formula (■) can be prepared by standard methods described in the literature.

Noketones of the general formula (■) that are difficult to produce by conventional methods, for example, R is -CH2CH2-Z f and R is non-1
The ketone of general formula (■) is a substituted tertiary butyl group.

It can be prepared by separate hydrolysis of a diketone corresponding to the general formula (■aG 11I (in the formula, tBu represents a tert-butyl group). For example, the formula ('vM
Compounds of &) may be prepared by treatment with a base such as sodium hydroxide at 0°C to 10°C in a convenient solvent such as ethanol or methanol. The product may be isolated by pouring the reaction mixture onto top water and extracting with a suitable solvent.

The compound of general formula (■a) is 2. -1,6-tetramethylhebutane-3,terdione R'-Hallmano is 11 sulfonate in a solvent such as ethanol, methanol or dimethylformamide 20,10
It may be prepared by reaction at 0°C in the presence of an acid binder such as potassium carbonate.

General formula (■) and (■) fhiaimonoke, -7 throw formula (■
a) or (■b): Compound of (■a) (■b) (wherein R1 and R5 have the above-mentioned meanings) and an organometallic compound of general formula (■a) or (fVb) It can be prepared by reaction with

Compounds of general formula (■) are prepared using standard methods described in the literature.

The compound of the general formula (ID) is Mabuko, the general formula (■): the triaryzolyl epoxide, -a2m:R'M
(X) (wherein R has the abovementioned meaning and 1M is gold-14, preferably copper) by reaction with an organometallic compound which can be represented by (X). Reaction)1. -10°C in diethyl ether or tetrahydrofuran 20% solvent
It is convenient to carry out the reaction at +-20°C under an inert atmosphere. The product is isolated by quenching with the proton donor.

The organometallic compound is the corresponding magnesium or IJ
Thium organometallic compound and Cui or CuBr.
Copper(I) salt such as SMθ2 complex? It can be conveniently prepared by reacting between θ and θ°C.

Compound (■) is described and known in the literature (e.g. D
f:3//I/23g).

R' 7b: M-C)12cH2-X f fQ
Le $ Expression ([)ノ'7 Le* JL.

Asoryl alcohol, corresponding alkynol (X)
: FL3-CH2-Cmic-x (XI),
Methanol, ethanol, etc. can also be reduced using hydrogen in a suitable solvent such as acetic acid in the presence of a suitable catalyst such as noradium supported on carbon (or other carrier) to obtain fA1! ! ! Get L. When the side chain R1 contains a chlorine such as chlorine, etc., when such acetylene is reduced as in ('A), in some cases, the halogen is decomposed and removed by the hydrogen system. In this case, the corresponding hydroxy-substituted acetylene compound is reduced with gold,
A proxyl group may be converted to a halogen group by conventional methods.

The plant growth regulating action of the compounds according to the invention is manifested as an inhibiting or inhibiting action on the growth of woody and herbaceous monocots and dicots. Such a suppressive or inhibiting effect may be achieved, for example, in peanuts, cereals (e.g. wheat and barley).
, Oil 5eedraps”, field beans, sunflowers, potatoes and soybeans, where it strengthens the stems, increases the stem diameter and shortens the stems by reducing the stem height. , shortening of interpartum, increased formation of buttress root', more upright fc stem shape and leaf orientation (o
All beneficial effects such as rlentation (rlentation) can be achieved without the addition of a total reduction in the risk of lodging and an increase in the amount of fertilizer to be applied.

The growth inhibitory effect of woody plants is useful for inhibiting the growth of hanging plants under power lines. The inhibitory or inhibiting growth compounds are also useful in altering the growth of sugarcane stalks, thereby increasing the number of sugar canes in the cane that blooms at harvest. Regarding sugar cane, flowering and ripening can also be controlled by applying the compound of the present invention. Growth suppression in peanuts can aid yield. Controlling turfgrass growth helps maintain it. Examples of suitable turfgrasses are stethulum, secundatum (3t@notaphrum ae).
cundatum) (Augustine group), Cynoslus, cristatanii (Lolium Perenne),
Agrostis, Thenu (Cynodon dactyl)
on: Permew Douglas);
stuca 5pp), for example Fuesca.

rubra (Fe@tuca rubra) and Boa (P.
oa spp, such as Boa, Poa p.
latense).

The compound of the present invention suppresses the growth of turfgrass without causing significant phytotoxicity or adversely affecting the appearance (particularly color) of turfgrass. These compounds are also effective against the development of flower heads in turfgrass.These compounds also suppress the growth of weeds present in turfgrass. It also has an effect; such weeds include those of the genus Carex [for example, Cyperus '
) plants] and dicotyledonous weeds [e.g. daisies, obako, knotw-eed,
peedwell') thistle (thi-atele)-
docks and noborosu゛<(r+a
gwort). Non-crop plants [e.g. Mj
It or cover vegi tatio
n')] maintenance of cultivated and wild plants is facilitated. Protective turf grass (grass c.
ovsr) is important. However, it is necessary to substantially suppress the excessive growth of preserved turfgrass. The compounds of the present invention are useful in the above situations, since they completely inhibit the growth of protected turfgrass without killing it, which leads to soil erosion: at the same time, the consumption of nutrients and water by turfgrass is reduced, resulting in fruit The harvest t increases. In some cases, the growth of one grass is inhibited to a greater extent than the other; this selectivity is useful, for example, to improve lawn quality primarily by inhibiting the growth of undesirable grasses.

The plant growth inhibitory effect is effective for ornamental, household, home garden, and nursery plants (e.g., poinsettias, chrysanthemums, carnations,
It is also useful for reducing the size of tulips and daffodils.

As previously discussed, the compounds of the present invention are also useful for inhibiting the growth of woody plants. This property inhibits the growth of fruit trees (e.g. apples, pears, cherries,
It can be used to reduce the need for pruning or the bottom shape of peaches, peaches, etc.

The plant growth regulating effect (Vi) itself is an increase in the yield of crops, and fruit trees are manifested by an increase in the formation of fruits, grains and grains in other crops.

Certain coniferous trees are less inhibited in growth by the compounds of the present invention, and therefore, the compounds are useful in controlling harmful plants in conifer seedlings.

In the case of potatoes, both vine control on the farm and prevention of germination during storage can be used.

The compound of the present invention can be used as an abseision agent that thins fruit on trees and improves the quality of the fruit.
-nt).

Other plant growth-regulating effects elicited by the compounds of the invention include changes in leaf shape and changes in leaf morphology, both of which allow for more light to be blocked and utilized, and in monocotyledonous plants. Improving light interception is essential for all of the world's major crops, including wheat, barley, rice, corn, soybeans, sugar beets, potatoes, cultivated plants, and fruit trees. It is valuable for crops.The effect of changing hazuki is
For example, it is useful for changing the orientation of potato leaves, thereby allowing more light to fall on the crop and increasing light density and tuber weight. By promoting tillering of monocot crops (eg rice), the number of flowering shoots per unit area can be increased, thereby increasing the overall yield of such crops. Furthermore, classification stepwise (hi@rarc-h
Good control and modification of the relationship (lcal) is possible both during the growth and reproductive stages of true cotyledonous and dicotyledonous plants, especially cereals such as wheat, barley, rice and maize, thereby reducing the flowering per unit area. It can increase the number of shoots and change the grain distribution within the ear, increasing yield.

In the treatment of rice, the compounds of the invention may be applied, for example, as granular containers or granular formulations, e.g. as slow-release granules, in seedling boxes (n
ursery box)%paddy water
t-er) and other growing areas and media.

Rice (Cpaddy rice) may be treated by applying the granules by dipping. Lawn grass, especially garden TM Ko lawn (AME
In the case of ni tygrass '), increasing the density of the turf by one can increase the density of the turf, resulting in increased resilience to abrasion, and also increase the yield and quality of forage turfgrass; e.g. and preference FIF (pala
tab -tttty) increases.

Also, treatment of plants with compounds of the invention can result in leaves that take on a deeper green color. In the case of dicotyledonous plants such as soybean and cotton, sideg-hootin
g) is promoted.

The compounds of the present invention can inhibit or at least delay flowering of sugar beet (thereby reducing sugar yields), but also alter the flowering morphology of many other crops. be able to. Furthermore, the compounds of the present invention can reduce sugar beet size without significantly reducing sugar yield, thereby increasing cultivation density. Similarly, other root crops (e.g. turnip, sx -)' (sw@de), ma
ngold), American pout (parsnip)
), beat, yam (y, 1m)b and casano”
(caasava), the total cultivation density can be increased.

The fjAFi of the present invention may also be useful for inhibiting the growth of cotton plants, thereby increasing cotton yield. Harvest index (harvest index) is determined by varying the partitioning of dry material.
Crop yield can also be increased by improving the yield (i.e. yield as a proportion of total dry material produced).
Applies to all pod crops, tall crops, cultivated VF crops and fruit crops.

The compounds of the invention can retard the emergence of 100 seeds from 8i seedlings, reduce the height of the stems and delay flowering, thus making the plants more resistant to load: this property can be applied to large quantities in winter. It is useful for protecting plants from snow in areas where snow is present; the reason being that the treated *Mi plants remain under snow throughout the winter. Moreover, the compounds of the present invention can render certain plants fire resistant to early drought damage.

When the compound of the present invention is applied as a seed treatment agent at a low rate, it exhibits a growth stimulating effect on plants.

It should be fully understood that not all of the compounds of the present invention necessarily exhibit all of the plant growth regulating effects as described above. Advantageous among these compounds are those that exhibit a wide range of growth regulating effects on a wide range of plants. However - compounds exhibiting greater than 1% activity with respect to specific plants and/or specific plant growth regulating effects are useful as well. tarnperate cereal')
The examples show that it is very effective as a growth retardant for A. b. Compounds of the invention generally have a long interligul length.
arlsngth), but this is due to the long interpartial length and interno.
Fig. 2 is an example of a reduction in depth and thus a restriction in the forward direction of plant lodging. For woody plants such as apples and apples, the compounds of the invention generally act as retarders and are therefore useful as plantation management aids (
field manag@m+snt aid'). The compounds of the present invention typically exhibit substantial green-up along with plant growth regulating activity.

It has the same green up effect and can affect tillering in grains, thereby increasing the number of ears and thus the yield.

Some of the compounds of the invention perform a more specialized type of action. That is, for example, the compound layer of the example core! has less activity on barley and rice, but is very active on apple, showing substantial activity even at lower applications.

In carrying out the plant growth regulating method of the present invention, the compound to be applied to regulate plant growth may be affected by a variety of factors, such as the specific compound selected for use and the growth control method. It will vary depending on the type of plant to be trimmed. However, typically 0.0/,11. Preferably an application rate of 01 l-jkf/hectare is used.
Ru. Biodegradable polymer slow-release granules (biodegrada)
b4e polymeric slow release
granule ) f When using / , /
Q? /ha is preferred, whereas lower application rates can be used in electric spraying methods.

However, for certain plants, applications within this range! Even undesirable phytotoxicity may be present at all. Accordingly, routine experimentation may be required to determine the best application rate of a particular compound for a particular purpose.

While the compounds of the present invention may be used as such as plant growth regulators, they may be conveniently formulated into compositions for use for such purposes. According to the invention, therefore, the general formula ill
A plant growth regulator composition is provided which uses a compound or a salt thereof or a metal complex thereof as an effective nuisance.

According to the present invention, compounds of the general formula m or their salts or metal complexes are added to plants, plant N- or plant compounds Vi
A method for regulating plant growth is provided, which is characterized in that the method is applied to a place where seeds are growing.

The compounds of the invention, their salts, metal complexes, ethers and esters can be applied in various ways; for example, they can be applied directly to the leaves of plants, with or without formulation, and to shrubs or Can be applied to trees or Vim or other media in which plants, shrubs or trees are growing or to be planted, or by spraying or dusting, or as a cream or paste preparation, or in the form of a vapor, or with delayed release. Can be applied in granule form. Application may be applied to any part of the plant, shrub or tree - such as leaves, stems, branches or roots - or to the soil around the roots or to the soil before sowing, usually by adding water to the soil.
paddy water) or a hydroponic culture medium system. The compounds of the invention can also be injected into plants or trees, or applied to plants using electric spraying methods.

As used herein, the term "plant" includes seedlings, shrubs and trees.

The compound of the present invention is preferably used in the form of a composition for agricultural and horticultural purposes. The type of composition used will vary depending on the particular purpose intended.

The composition comprises the active fraction and a solid diluent or carrier, such as kaolin, bentonite, diatomaceous earth, dolomite, calcium carbonate, Merck, powdered magnesia.

It may be in the form of a dispersible powder or granules consisting of fillers such as Fuller's earth, Hewitt's earth, diatomaceous earth and china clay. Such granules may be preformed granules suitable for application to soil without further treatment. These granules can be prepared by pelletizing a mixture of the active fraction and powdered filler, in which the filler pellets are impregnated with the active ingredient. The composition for seed dressing may, for example, contain an agent (such as mineral oil) that promotes the adhesion of the composition to seeds; Using seeds for active fraction? It can be a formulation for dressing.

! The material may also be in the form of a dispersible powder or granules containing a wetting agent to facilitate the dispersion of the powder or granules in a liquid; such powders or granules may further contain fillers and suspending agents. May contain clouding agents.

Aqueous dispersions or emulsions are prepared by dissolving the active fraction in an organic solvent which may optionally contain a wetting agent, dispersing agent or emulsifying agent, and then dissolving the resulting fc mixture into an organic solvent containing a wetting agent, dispersing agent or emulsifying agent. It can be prepared by adding a knife to the water obtained. Suitable organic solvents are ethylene dichloride and inpropyl alcohol.

Brohylene glycol, diacetone alcohol.

Toluene, kerosene, methylnaphthalene, xylene, trichlorethylene, furfuryl alcohol.

Tetrahygrofurfuryl alcohol and glycol ethers such as λ-ethoxyethanol and λ-butoxycetanol.

, /'/ /'//' , /', / Spray composition ri also. The formulation may also be in the form of an aerosol, held in a pressurized container in the presence of a propellant, such as fluorotrichloromethane or dichlorodifluoromethane.

The cultural compound is dried and mixed with fire smoke mixture (pyrotech).
- former cm1xtnre) to form a composition suitable for generating smoke in a closed space containing said compound.

Alternatively, a compound of the invention may be used in the form of microcapsules. Additionally, this compound allows for a slow and controlled release of the active ingredient.

It can be a biodegradable polymer formulation.

Appropriate interlocking machining 1. For example, spreadability to the surface to be treated.

By incorporating a finishing treatment to improve adhesion and rain resistance, one can better adapt a variety of compositions to a variety of intended uses.

The compounds according to the invention can also be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorous-containing fertilizers). Preferably, the composition consists only of fertilizer granules in which the compound is incorporated, for example, into a coating. Such granules contain 2! of active compounds! It is appropriate to contain it in an amount of % weight or less. Therefore, if the present invention is ↓, furthermore.

Fertilizer compositions containing a compound of general formula tI+ or a salt or metal complex thereof are provided.

Furthermore, the compositions are usually aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surface-active agents, such as wetting agents, dispersing agents, emulsifying agents or suspending agents. Immersion liquid or 1! Either in the form of a liquid formulation for use as a nebulizer, the masher can also be in the form of a nebulized formulation suitable for use in electric nebulization methods. Such drugs are cationic,
It can be an anionic or nonionic active agent. Suitable cationic activators are primary ammonium compounds such as cetyltrimethylammonium bromide.

Suitable anionic surfactants include soaps, salts of aliphatic monoesters of sulfuric acid (e.g. SuI-IJ umlauryl sulfate), salts of sulfonated aromatic compounds (e.g. sodium
Dodenlebenzene sulfonate.

sodium, cal/lam or ammonium lignosulfonate, butylnaphthalene/sulfonate and a mixture of the sodium salts of diisopropyl and triisopropylnaphthalenesulfonic acids).

Suitable nonionic activators are ethylene oxide and aliphatic alcohols such as oleyl alcohol or cetyl alcohol or octylphenol.

It is a condensation product with an alkyl phenol such as nonylphenol or octyl cresol.

Other nonionic surfactants are partial esters derived from long chain fatty acids and hequintole anhydride, condensation products of the partial esters with ethylene oquinide, and lecithin.

Suitable suspending agents are, for example, hydrophilic colloids (for example polyvinylpyrrolidone and sodium chloride/methylcellulose) and vegetable gums (for example gum arabic and gum tragacanth).

Compositions used in the form of aqueous dispersions or emulsions are usually supplied in the form of concentrates containing a high proportion of the active ingredient;
Dilute with water before use. Such concentrates often withstand long-term storage and, when diluted with water after long-term storage, remain sufficiently homogeneous to be applied with conventional equipment or electric spray equipment. It is necessary that the water-based material 41 can be completely formed. This undiluted solution is conveniently applied! Weight is easy or less, suitable VCVi10~! j% by weight 1 eg λJ-~60 may contain 1% by weight of active ingredient. This is rich in lano! i, diorganic acids (e.g. xylene sulfonom
It is suitable to contain all alkaryl or aryl sulfonic acids such as dodode/rubenzene sulfonic acids;
The solubility of the active ingredient in the polar solvent used in the concentrate is increased.

It is appropriate that the concentrate also contains a high proportion of surfactant, so that emulsions which are sufficiently stable in water are obtained. When diluted to prepare an aqueous formulation, 7) the formulation contains varying amounts of active ingredient depending on its intended use, but generally o, ooor (usually o, oi) to Aqueous formulations containing 10% by weight of active ingredient can be used.

The compositions of the invention may further contain other biologically active compounds, such as compounds with similar or auxiliary fungicidal or plant growth regulating activity, or compounds with insecticidal activity. obtain.

Other mothicide compounds 81 include grasses (e.g. wheat)
vr) diseases such as 5eptoria, Gihhere
1 seed of the genus Helminthoporium can be used to eradicate soil-borne diseases such as downy mildew and powdery mildew of grapes, powdery mildew and rot of apples, etc. Other sterilization 41
The following compounds can be mentioned.

imazalil, -nomyl, karingenome, thiophanatemethyl, captofol, captan, -suzuki, trifoline, dodemorph, tridemorph.

Pyrazophos, fralakiflu, ethyrimol, technazen, 7-methylimole, bubirimate, chlorothalonil, vinclozolin, f/midon, iprodione, metalaki/ru, forcetyl-aluminum, carboquine, oki/cal+Irquine, fenarimol, nuarimol, fenflam, Mesfuroxane, nitrotal-isopropyl, triadimefone, thiaR-dazole, II) azole, triadimenol, pyroxazole, dithianone, binapacryl, chinomethionate,
Guaditin, Dodine, Fentin Hydroxide, Dinocab, Folpet, Diclofluanid, Citarimphos, Quikudin. Cycloheximide, dichlorofl-razole, dithiocarbamate, @compound.

Mercury compounds, /-(2-'/anorcomethokifiminoacetyl)-3-ethyl, urine i, fenapanil, olefus, propiconazole, etaconazole, fenpropemorph, fenbrohisin〇 Compounds of general formula tIl are soil The peat or peat may be mixed with other media to protect the plant from spray diseases that occur on the rice, soil or leaves.

Suitable insecticides include pyrimol and cloneton.

Diphthoate. Mention may be made of metasysdox, pyrethroids and formothiones.

Other plant growth regulators may be used to control weed growth or seeds.
dheqd) formation and plant growth of the compound of general formula fI)! The level or persistence of J4 activity improved.

These compounds are compounds that selectively suppress the growth of undesirable plants (for example, miscellaneous plants), or make compounds of the general formula (Tl) act rapidly or more slowly as plant growth regulators. Some are herbicides.

Examples of suitable plant growth regulators that exhibit a synergistic effect when mixed with the compounds of the invention or are used in combination with the compounds of the invention include:
gibberellin (e.g. OA3mOA4 or OA,
), auxins (e.g. indoleacetic acid, indolebutyric acid, naphthoxyacetic acid and naphthylacetic acid), kutokinins (e.g. kinetin, diphenylurin, benzimidazole, benzyladenine or benzylaminopurine), %phenoquinacetic acid (e.g. λμ-ri) 7t is MO
PA), substituted benzoic acids (e.g. triiodobenzoic acid) 1
Morphactin (e.g. evachlorfluorecol), Frey/Hydrazide, glyphosate, glyfosine, long chain fatty alcohol '17td fatty acids, dikegranoque, fluoridamide, mefluidide, texμ class ammonium and phosphonium compounds (e.g. chlormequat, chlorphonium or 7tH mepic) atochloride), etepone, carpetamide, 3,6-dimethyl loromethylanisate, daminozide, aslam, abubunic acid, impyrimol s'(''-chlorophenyl)-μ, t--, > May-2 -Oxo/, pyridine-3-carzenic acid.

Hydroxybenzonitrile (eg, t is bromoxynyl), diphenzoquart, benzoylprop-ethyl, 3. t, -) Chloropicolinic acid, fenpentezole, triapentanol, flurpyrimidol, nozoclobutrazol, tetocycla/suotechnazene. Among the above compounds, the additive effect will most likely occur when used in combination with μ-class ammonium compounds, especially the compounds marked with an asterisk.

Certain Application Methods 1 For example, the compounds of the present invention may be applied to Takagi or
In the method of injection into plants, it is desirable that the compound has a relatively high solubility in water, for example 30 ppm or higher. The compounds can be formulated for use in the form of aqueous solutions, eg, solutions in lower alcohols.

In certain application methods, to prevent migration to adjacent crops or, in some cases, to crops subsequently planted in the same soil.

It is desirable to have low persistence in soil. Preferably, the compounds used in such application methods have a half-life in the soil of 20 weeks or less.

Examples of the present invention are shown below.

This example is shown in Table 1, Compound No. /, 2-dimethyl-3-hydroxy-3-(!!-butyl)-μm(
1, λ, tA-)lyazol-yl)-butane production.

n-Butyllithium (i, rsMfa solution in hexane)
Chlorozirconium-tri-n-phthokizoto (20 ml of a 20M solution in diethyl ether) was added to a mixture of J ml ) and anhydrous diethyl ether (jamg) at -10C under a nitrogen atmosphere. The mixture was stirred at OC for 1 hour and then diluted with 2.
iodimethyl μm (l.

A solution of 1A-triazol-7-yl)-butan-3-one (2,Of, 12 mmol) was added and the reaction mixture was warmed to room temperature and stirred overnight. Pour the reaction mixture into dilute hydrochloric acid (o, tM) and adjust the hole diameter.

Extract the aqueous phase with ethyl acetate. The mixture of ethyl acetate extracts was washed with water, saturated sodium bicarbonate solution, then brine, dried and concentrated under vacuum to give a yellow oil. Chromatography was performed on silica using gradient elution (ethyl acetate, 20-10% in petroleum).

The product was obtained as a yellow oil.

NMFL (○DO+,,)δ 0. lo-1,60(
I1 day, complex), 2.92 (/H, s
).

≠, 3θ(koH*s) *7a 5'<4 (
/H@s) ar, /A(/H,s).

IFL (film) 31tO-3700 (strong absorption).

3! KoQCr1g.

m/e noM, 210. /41. llA3.1
2゜This example uses a triazolyl alcohol having the following formula: 2.2-dimethyl-3-hydroxy-3
-(n-pentyl)-μ-(/, co.

An example is shown in which μ-triazol-l-yl)-butane is produced in two steps.

Step I A suspension of sodium hydride (I0%) (upper IA7f, 0.//jM) in anhydrous dimethyl sulfoxide (rOaj) was prewashed with petroleum ether (μo-6o0).
The mixture was heated at C for 2 hours. After cooling the mixture to room temperature, anhydrous tetrahydrofuran (rOl) was added and further OC
Anhydrous dimethyl sulfoxide (70 ml) was added while maintaining the temperature of the mixture below 3.)C.
trimethylsulfonium iodite (23, A3) in
, 0.111 mol) was added dropwise. After the addition of the trimethylsulfonium iodite solution was complete, the mixture was stirred for at least 1 minute and then diluted with anhydrous tetrahydrofuran (uOm
2,2-dimethyloctane-3-o7(I2,
0? , 0.07-F nyl) and -a, OC
After stirring for 1 hour, the cooling bath was removed and the reaction mixture was stirred for 16 hours. The reaction mixture was then poured into water and extracted with ether. The mixture of ether extracts was washed with brine, dried and dried with anhydrous MIS04), then the ether was removed under vacuum to yield the epoxide as a yellow oil, which was used without further purification.

Process ■ Production of triazolyl alcohol Sodium hydride (50%) in anhydrous dimethylformamide (jj; 01d) (=tty, o, oμjM)
1. λ, 4t-triazole (3, Of, α
oarM) was added little by little and the reaction mixture was heated at room temperature for 2 hours.
After stirring for 0 minutes, the epoxide prepared in Step 8I was added dropwise. The resulting mixture was heated at roC for 4 hours and then heated to
The mixture was heated vigorously at C for 3 hours. The reaction mixture was then cooled and dimethylformamide was removed under vacuum. The residue was partitioned between total water and ether, the m0 ether phase was removed, and the aqueous phase was further extracted with ether. Mix the ethereal extracts and wash with brine.

Anhydrous M,? Dry over SO4 and evaporate. The residue was chromatographed on silica using gradient elution (ethyl acetate (0-100%) in gasoline) to give the triazolyl alcohol (r, co9) as a charcoal red oil. When left in an oily substance, a cream-colored solid forms.When mixed with gasoline (μ0-60), a white solid (
Melting point 74tj -77,6C) was obtained.

NM, R(ODO+3)δ/-0(9H,s), O,
Otsu-87 (//H, Complex).

Ko. 9 (IH, Broad 5) I U, 3O (λH, S), 7.5'! (ll(,s), J
', /J'(IH,s).

It”L (l [membrane) 2600-3700 (strong absorption) L
yn.

m/e noM”, 2214./12./61,1 Tough, 13°70° , the entire preparation of compound No. 3) is shown.

The triazolyl alcohol (/-2o) prepared in Example
y, o, ootM) and anhydrous dimethylformamide (IO
Sodium hydride (0%) (O
, x is f, 0.00! Add M) little by little. The reaction mixture was stirred at room temperature for 20 minutes and then diluted with methyl iodide (θ-7
/f, 0.00jM) was added dropwise.9. 1 of the obtained mixture
After heating for rOC''''cj hours, cooling and removing the dimethylformamide under vacuum. The residue was partitioned between water and ether. The ether phase was removed and the entire aqueous phase was extracted with ether. The ether extracts were combined, washed with prine, dried over anhydrous M, #SO4 and evaporated and the t0 residue was chromatographed on silica gel using gradient elution (ether 0- in gasoline).
100% L'-methyl ether (0, ψg?) was obtained as a pale yellow oil. tO NIIJR (ODO+3) δ0. If(31-1,t
), /, 00 (9H, s), /, /-/, Otsu (41
-1, complex),,,? , JO (JH,s).

j, J (7 (2H, AB Cultit).

7, Its (IH, s), L12 (IH.

s).

IR (liquid qi > , 2roo-3oso (strong absorption).

J/J (7 (weak absorption) cm.

m/er+nM, jJJ', 12. 2≧, /95/12
．． /71° This example is a triazolyl alcohol having the following formula: ], i.e., λ, λ-
Dimethyl-3-hydroxy'/-J(n-hex/l)-μ
m(/, 2.≠-triazol-!-yl)-butane (
An example is shown in which Compound No. (≠) in Table 1 is produced in a Koni process.

Process ■ Sodium hydride (50%) pre-washed with petroleum ether (4tO-OtsuO0) (J, 75ft, 0.07mm)
and anhydrous dimethyl sulfoquinide (/+20 mj)
A suspension of EA was heated at total tOC for 2 hours. The mixture was cooled to room temperature and diluted with anhydrous tetrahydrofuran (KO)'5.
r, and further cooled to OC. Trimethylsulfonium iodite (9 #, 0.07 rM) dissolved in anhydrous dimethylsulfoxide (I0) was added dropwise while maintaining the temperature of the mixture at or below 3C. After the addition was complete, the mixture was stirred for a few minutes and then a solution of 2. Korg methyl nonan-3-one (O-O!?, 0.039 M) in anhydrous tetrahydrofuran (OfflA) was quickly added. After stirring for 7 hours at oC, the cooling bath was removed and the reaction mixture was stirred for 166 hours.The reaction mixture was poured into water and extracted with ether.The combined ether extracts were washed with brine and dried. Anhydrous M#504
) The ether was then removed under vacuum to give the epoxide as a yellow oil, which was used without further purification in Step III Anhydrous dimethylformamide C! Sodium hydride (jO%+ (3,7! 9.0.071M+) in θ0rd)
in a suspension of /, 2. ≠-triazole (evening, ≠61.
After stirring the reaction mixture for 20 minutes at room temperature, all of the epoxide prepared in Step I was added dropwise. The resulting mixture was heated at 0° C. for 6 hours, cooled, poured into water and extracted with ether. The ethereal extracts were combined, washed with Bligh, dried with anhydrous MgSO4J and evaporated. Chromatography using #1 gradient separation method on silica (
NMR of ethyl acetate O-/θQ%J1 triazolyl alcohol (≠, A I?) in gasoline obtained as a yellow oil, (CD063 + δ /, 0
0 (ta F(,S), 0
．． 1-/, 7(/3H, complex" 2.♂2 (/H,s 14C, 25'(, 2H, sl.

'7. Ta ! (/H, s + ,,!, /41/I
−1°sl.

■a (qv membrane 1 2100-3700 (strong absorption) am
-1゜m/e noM+, /Riot, /7/,
/At, 13,70゜〜〜〜〜〜〜〜〜〜〜〜〜〜　〜　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　 for the compound in Table 1.

Preparation of Korg methyl-3-hydroxy-3-(nihebutyl-(/,2.≠-triazol-/-yl)-butane) Complete procedure 8I Hept-/-yne in anhydrous tetrahydrofuran (30 mel of Gg under nitrogen atmosphere, =
n-Butyllithium (/Jj M in hexane) at 70 °C
The resulting mixture was stirred for 7 hours. Anhydrous tetrahydrofuran (r
Om7! 22 in l. ! -dimethyl-≠-(/, 2.≠
-triazol-/-yl)-butan-3-one (6,
♂? , 1 mol) of ethyl acetate and HO were added to the mixture, and the resulting mixture was heated to room temperature. distributed. The aqueous phase was extracted with ethyl acetate, the combined ethyl acetate extracts were washed with water, sodium hydrogen carbonate solution and then with blister solution, dried and then washed with anhydrous VGSO, then washed under 90°C. Then, remove the yellow oil by chromatography on silica gel using ``7'' tilt method 1. = (2 ethyl ether in gasoline ro
-goc4+, the target compound of this step (λ, do7?), was obtained as an all-yellow crystalline solid (melting point: 7t-7?°C).

N~If ((CDC75) δ0.70- /, 00 (
3H, tJ7) 1zl.

/, / 0- /,! 0 (/J'to ■, co/brex l /, 1 0-2.10 (koH, complex 3.7 yo (/ j-1, s + ≠, J
O(!11゜s I, 7.P
ko; (/H,s I,r,/I(/
H, s +.

IR (Nujol) 30♂0-3Otsu0θ (strong absorption)
.

3/30,22! Ocm.

m/e no, M", 2'AI, 20 Otsu, 7I
I, Z2゜ Elemental analysis Theoretical values for 015H25N30: O, A r, I+ 0: )(,?J
7.

N, Grouper j% Actual value: c, x za, 3 r; H, ? ,tA3
.

N, grouper 0% Step ■ Alcohol prepared in Step I (/l, 0.03 g mol)
Catalyst with radium supported on ethyl acetate (10% on carbon in a solution consisting of Omi I) (o, s y
The resulting fc rock solution was hydrogenated under hydrogen pressure of AOpsi for 30 hours. The reaction mixture was then filtered through a moist Hyflo filter.

The organic phase was washed with water and brine, dried and dried with Mg anhydride.
5o4) and then evaporated under pure nitrogen to obtain a crude product.

Chromatography was performed on silica using a gradient bath method (diethyl ether in Ganrin, 2O-lrO
%), objective of this process &# (0,l=t f J
was obtained as an oil.

N~IUL(Of)OA31δθ,t O-/, 1. θ
(2 Hiro H, Complex I, 2.14 (/H
, s].

≠, 30 (2'H,s J, 7. Octopus (/H2S
1 + 17 A! 'H+S
I.

IFL (Film) 3/7yo-31,00,3/
2j (weak absorption J.

m/e 2A6.2!2.2/θ, it
s, itt.

♂2.

Practical row 6 This practical row is g1 table, compound A A , i.e., λ, 2
-dimethyl-3-hydroxy-3-(Hiro-methyl-/-
butyl)-≠-(/+,!*≠-triazole-/
- shows the production of ylnobutane.

Step I Preparation: Stirred mixture consisting of hinoroyl chloride (I, 0λ9, 0.0 j morphic copper(I) iodide (o, 10 y, o, 6 mmol) and anhydrous ether (j Om/I) The mixture was mixed with isoamylmagnesium bromide (magnesium pieces (/J?, 0.07 J mol) and isoamyl bromide (7,J, 0.0 J mol) in anhydrous ether (70 ml) at -60 °C under a nitrogen atmosphere. After removing the cooling bath, the reaction mixture was stirred for 72 hours, carefully poured into water-cooled salt solution, extracted with ether, and the combined ether extracts were saturated. Washed with a sodium bicarbonate bath and brine, dried and anhydrous and then evaporated. The residue was chromatographed on silica using a gradient elution method (dichloromethane yO-30% in gasoline). ), a process to obtain the ketone as a pale yellow oil. A suspension consisting of the ormorph and anhydrous dimethyl sulfoxide (700 ml+) was heated at 10° C. for 2 hours and the mixture was cooled to room temperature. Anhydrous tetrahydrofuran (10 ml) was added and further cooled to 0° C. Anhydrous dimethyl sulfoxide C1rO− t+P
) was added dropwise to intoxicated trimethylsulfonium iodite (/0.2?, 0.0! mol j) while keeping the temperature of the mixture at 3°C. After drying, the mixture was soaked for 7 minutes, and then mixed with the ketone obtained in step 1 and anhydrous tetrahydrofura/(2θgoff), and stirred at 0°C for 1 hour. The cooling bath was removed and the reaction mixture was stirred for 72 hours, then poured into water and extracted with ether.
Wash the ether extraction snout with brine, dry and rinse with hot water.
g5041 was then removed under ether τ nitrogen to give the epoxide as a pale yellow oil, which was used in the next step without further purification.

Process-derived anhydrous dimethylformamide (2Ord J in sodium chloride (!
In a suspension of /, co, φ-triazole (2,07f.

After stirring the reaction mixture at room temperature for 20 minutes, the epoxide prepared in step (2) was added dropwise. The resulting mixture was stirred at tro.degree. C. for 6 hours, then cooled, poured into water and extracted with ether.
[on O4] and then evaporated. The residue was chromatographed on silica using a gradient separation method (10-100% in ethyl acetate in gasoline) and triazolyl alcohol (compound &l, ) (/, 71f) (melting point j 9
-A/J°C) was obtained as a white solid.

N'da (ODO431J O,7j (J H, dJ
7HzJ, OJO<JH.

dJ7Hz J, /, 0 / (riT-1,s)
.

Hao-i, t<rH, complex J, 2. Ij (JH, S J , u, JO (2H,
sJ, 7. Ta j (/H,sJ.

r-/! (/H*s).

Ia (Nujol 330!0-3410<strong absorption Jc
m-”.

m/e 2440, 2 cores a, it cores, 13
, 70.

Practical row 7 This practical row corresponds to Table 1, compound point 7, i.e. 2,2-dimethyl-3-hydroxy-J-(J-methy/I/-l-
Figure 2 shows the production of 2.μ-triazol-/-yl-butane.

Step I A 3M solution of ethylmagnesium bromide (in diethyl ether) in anhydrous diethyl ether (30 ml) (
A solution of 3-methyl=!-pentyne (
j t , 0.04 mol) was added. The resulting mixture was heated under reflux for 1 hour and then cooled to 0°C. Anhydrous dichloromethane 7 (/j Om
2,2-dimethyl-hiro-(/, co, 4/-triazole-/-ylhuptan-3-one (Ir, 1
1 F, 0. The Or-Erk Jos solution was slowly added and the mixture was stirred for ≠j minutes to form a gelatinous precipitate. Add ammonium chloride solution to this mixture, separate the organic 81, wash with water and brine,
Dry over Mg5OJ and evaporate under vacuum. The residue was chromatographed on silica, eluting with ethyl acetate in gasoline (!0-100%) to give co,2-
Dimethyl-3-hydroxy-3-C3-methyl-/-pentyn-/-yl J-≠-(/, 2.4A-triazole-/-ylnibutane(g, 222), all white solid (
(melting point: 60°C).

Step ■ A catalyst (0,j
The reaction mixture was hydrogenated for J days under the hydrogen pressure of A Opsi. The reaction mixture was filtered through [Iflo], washed with ethyl acetate, and the solution was evaporated and pressed to dryness to give a crude product. The product was subjected to column chromatography on silica using a gradient elution method (diethyl ether J1 in gasoline was obtained as an oil) and showed the following properties.

NMR (0DOt5 + δ /, 0 / tH, S
I, 0.1rr-1,71° (/3H, complex).

20g (JH, Complex): 4t, 30(2H, sJ, 7.?I(JH.

S4,1. /A(/Fl, sl.

IR (Finimu) 3 / AO-3700 (i
= absorption j3/20cm.

m/e 2! II (MHL, 23
1, /ri5/7/.

/AT, 12, j7° elemental analysis c, 4H27N30. Theoretical value:
C, J A, j 7: H, / 0.7 +: N
, / J, j♂chi.

Actual value: O, At, 09; H, / /,
,27:N,/J,/7%.

Implementation queue! Table 1, Compound &t1, i.e. co,2-dimethyl-3
-Hydroxy-3-(Hiro-methyl-/-pentyl)-G CI, 2.≠-triazole-/-ylnobutane was prepared by hydrogenation of the corresponding °alkyne using the general method of 11HJ 7. .The product was a white solid with a melting point of Hirokazuhiro♂°C and had the following characteristics: N'JR1 (CDO431δ 0.t A f
& H, d l , /, 00 (PH,.

s l , 0.41'l-/, 6f t 7 H, complex), 2. To, 2 (/)l.

s l, 3. / Do (2H, sl, 7.
ri6(/H+sJ+”,' Otsu(/H
, sl.

Ile (Filmfu 3/Hiro!-3700 (strong absorption)
.

3j20cm.

m/e uj'i4(MH), 231r
, 220. /Riotsu.

/Otsur, 13. tough.

Elemental analysis C14H27N50 Theoretical value for VC: 0, A 4.3 A; II, / 0
．． 7 Hiro-N, /it I Section.

Actual measurement value: c, g J-, ri0: H, /
01.3: N,/iA 3%.

Implementation List Table 1, Compound Jra? , i.e., λ,! -trimethyl-3-hydroxy-3-(j-methyl-/-hekinrenauhiro-(/,j,≠-triazol-/-yl)-
All butanes were prepared using the general method of Example 7 by hydrogen cutting the corresponding alkynes. The product was oily and had the following properties: NM[((ODO43)δO1, Y −lj O(,
2≠11, Complex I,,24)(/H,s
l.

g, j O(jH, s J, 7.9μ(/[Ils
l, 1. / j (/ :l,
s l.

HNfilm) 3/! ;0-3 Otsuya O (strong absorption).

J/+2jcm.

m/e'No"J", 2j2. ．． 210.
/I! ,! r2゜+7゜Run 10 Table 1, Compound No. 10 was prepared by combining the general method of Row 7, and the product (/ : / , ) astereomer mixture, ``Mado'' was oily, It has the following properties: NMR (ODO23Jδ0.t & -/, A j (
24LH, complex), 2J7 (/I-1, sl
.

Hiroshi, 30 (2H, 97, 7, Rij (/H.

sJ,? ,/Otsu (/ H, sl.

IR+Film) 3/10-3630, 3j30
cm.

m/e No'A", 2!2., :Jl
o, /Ita, fλ.

+7 + Real! J series // Table 1, Compound No. // Total fruit 7if [1 The product prepared using the general method of Example 7 was a colorless oil and had the following properties. ~IR(CL)C43)120. Yo0-/, 70 (
,2≠14. Complex SF 9.2. Ryo2 (/H,
s I.

41, OJ' (,! t-1, s 1,7.2≠(/
I-1.

s), J', / Otsu (/
H,s I.

I[Nfilm) 3/AO-31rl
AO, 3j20cm-'.

m/ e No ・XA++ -2/ O
T/nij, 12,37° real row/ko Table 1, compound'! '/J cup/λ, that is, -1・
Trimethyl-3-hydroxy-J-+3.3-methyl-
/-butyl)-ru(/,λ,μ-triazole-/-
In the first step, the pig 7 was treated with 2. Ko.

It was prepared using the general method of the actual Mi [flJ t, except that co, λ-dimethyl-promobumene was used as the raw material for preparing -dimethylhebutan-3-one.

The product has a melting point of 7A-7! It was a white solid at r°C and had the following properties.

NMR (ODO431δ0.71 (9)T, s
+ , /, 0tI (9'Ff.

S), 0. ≠-7 trap (4LH, complex no, ko, ri (/H, s l.

≠, 32 (, 2H, s I , 7.9A (
/H.

s), J',,! 6 (/II, s)
.

■Le (Filmno 3/1.0-3700, 3/, 2
CN weak absorption no Cm.

m/e No'vl, 23g, /rit,
12゜Embodiment/3 Fujiganhi 41 is shown in Table 1, Production of Compound) Zu62.

Process l Production of propan-2-one This manufacturing step 1 was performed under an argon atmosphere.

Tetrahydrofuran (t-butyl alcohol in 20 ml (≠, Takota J's extract > tt)
Lithium t-butoxide solution obtained by dropping n-butyllithium (lj M bath solution, 1 g) at °C:
It was heated to θ°C and added to a stirred solution of cupric iodine (/λ, A j ? +) in tetrahydrofuran <30 ml. After about 1/2 minutes, the gray cupric iodine was A beige solid formed and the reaction mixture turned brown.The reaction mixture was then cooled to -70°C and (-butyllithium (
Grouper M solution 34t, o at J kM 3-cyclohexylpropionic acid chloride (I0,0?r (D cooled 7
The reaction mixture was then fermented overnight at room temperature by rapidly adding bath Q (-440"C1) for an hour, quenching by adding methanol (30 ml), and then fermenting the reaction mixture overnight at room temperature.
The reaction mixture was then diluted with saturated ammonium chloride/monium chloride solution (200
The aqueous phase was extracted with ether (300 ml) and the extract was washed with 7% sodium thiosulfate solution (200 ml) and dried over magnesium sulfate in the presence of charcoal. I did. I went to Koat/・
Obtain a bright red oil and distill it to obtain a colorless liquid (!Jl,t
This liquid turned yellow upon discharge. A dispersion of go% sodium hydride (washed with gasoline/7) in one-step codimethyl sulfoquinide (OJ, l) in oil. ≠7) was incubated at 60℃ under nitrogen atmosphere for 2 hours.
The solution, which had been stirred for an hour, was cooled to 20 °C, diluted with anhydrous tetrahydrofuran (Omel, and cooled to -j °C. l
After 70 minutes, a solution consisting of the product of Step I and tetrahydrofuran (!Omi+) was added.
Leave it for a day, then pour it into water and add gasoline (130-≠θ℃)
Extracted with. The product was extracted and washed with cash brine, dried and evaporated to give a yellow oil of 3.77 P? ! lk was used without further purification.

Process 3 Dimethylformamide (2! /, λ in m/’l.

A solution of ≠-triazole (co, / /?
．． 7 J 9 + 'i was added to gold-containing dimethylformamide (!Om/'). , 0. at 20°C. After stirring for several hours, a solution consisting of the product of step 3 (3,779+) and dimethylformamide (λ!rrn1.I) was added.

≠ the mixture! Stirred for a total of 7 hours at -rO<0>C, then poured into water and extracted with ether. The extract was washed with water, dried and concentrated to give a white solid, which was purified by thin layer chromatography. Then, the two compound shops in Table 1, namely,
1.2-methyl-3-hydroxy-3-cyclohexylethyl-F-(/, 2゜hiro-triazole-/-ylhuptan (melting point 1.3-A7℃, O1≠339). It is shown below.

NMR (ODO63J/, 0 (ta)
H, s I, 0.1111-/, 7
．． 2 (/j H, complex).

Ko, Za I (/ H, s l, ≠, 3 (λ1 (.

s I, 7. P A (/H, sl, J', /A
(/T(,s+.

IR (Nujol) 3200-31='10cm''
(ml, 301=θ-3/Ocm (wl.

Repeat the general procedure of Example I/3 using 3-7 clope/tylpropionyl chloride as starting material to obtain compound A-23, λ, of Table 1.

u -dimethyl-3-hydroxy-cyclopentylethyl-≠-(/, 2.4t-trianol-/-yl)-
Butane (melting point 7 K, -77 °C) This compound had the following properties: I [((Nujol I
3/410-3/1. Ocm (w+, 3/O-0-3AOO”(ml NMR(CDO43ノδo, sl-〇, 7O)(/ II
, :J7plexl, 0.7 &-/, 0
♂(,2+1゜complex l , /,0 (ri1
(.

sl, Ha/2/, 3yu(/)l, Complex', Ha3.2-/, 72(riH, Coreplex j, 2.2g(/to1, sl, 4
t, J t (jH, sl.

7.92 (/H, s), L/l (/H, s).

Implementation row/! This example shows 3-cyclopropylethyl-co, koshimethyl-3-hydroxy-≠-(/,+2.≠-triazol-/-yl)-butane (Table 1, Compound A 24')
Manufacturing of? Indicating step/λ, 2. A, A-tetramethyl-hebutane-3゜j-dione (/3.3?), cyclozorobyl methyl bromide <Y, Of), potassium carbonate I/0.2 r).

A mixture of trace amounts of potassium iodide and ethanol (≠0 at) was refluxed for 76 hours. Most of the solvent was evaporated, water was added to the residue, the mixture was extracted with ether, the extract was washed with water and then brine, dried and concentrated to give 3.07 t of a yellow oil. This was distilled using a water pump until the temperature of the head of the distillation apparatus reached /Hirohiro °C. The distillation residue was extracted with total ether and concentrated to give a concentration of A-j °C above the total melting point of the pure diketone. The diketone (J,!u Of I prepared in step 1 of step 2, obtained as a yellow solid) was mixed with 1j of sodium hydroxide (/, 10
Added to the warm solution of 1. The solution was refluxed for 6 hours, mydriatic for 2 days at room temperature, and then poured into water. The mixture was extracted with ether, the extract was washed with water, dried and carefully concentrated to give a ketone containing a small amount of ether (2.t total).
≠2) Using this product vl as it is, the target compound was prepared according to the method in Example 1/fc.

Sol-/-yl;-butane white solid (melting point Tough-J °C), NMR (000151 δ: 0./K (2H, m J
: 0.32 (21-1゜m I : (I' J
O(/H,rn): /-00(riHrs
I: / - / 01 j T (+ m): /, A
/ (,2H, m I : /, r O(/H.

s): 4', 2 g (2H, sl,
7.93 (/H, sJ: ♂, /, !; I/H, s) Actual turn 11/4 Not implemented 'Evening 11 is 2. λ-dimethyl-/-fluoro3
-Hydroxy-3-pentyl-≠-(/, 2゜≠-triazo lunoyl)-butane (mlfi, compound flattened/
A stirred solution of /-pentyne (ha!v, λλ mol) in anhydrous tetrahydrofuran (iAOml I) was added with n-butyllithium (2 mol) at -7°C under a nitrogen atmosphere. ,6M
Bath liquid me, 23 millimeters? After adding chlorotitanium tri-inpropoxide (/M solution coat 2 r
nt, -2,! 75 minutes after adding the 3,3-mol J in anhydrous tetrahydrofuran (20rd I)
Dimethyl-Hiro-fluoro-/-(/.

Ko, Hiro-triazole/-ilfuftan-coon (prepared according to the method described in German Patent No. 2J20.3/O) (Hiro, 0?, , 22 mmol) was added dropwise. After the addition was complete, ? Fi!, the mixture was allowed to warm to room temperature and held for 1/g hour.The reaction mixture was then poured onto total water and extracted with ether (2 x 2j Oml, l).

The ether solution was washed with saturated brine and anhydrous MgSO4
After drying on top, the solvent was removed. The resulting yellow oil was subjected to total chromatography (silica gel, gasoline/diethyl ether G syneresis) to give a yellow gum (2, 2).
Propargyl alcohol (2,3?
Hydrogen (A Opsi.
When the reaction mixture '#l was inspected by 7 fLc after introducing hydrogen (I) and shaking at room temperature for 2≠ hours, it was found that the cooling of the reactor was not completed, so hydrogen (l) was added to the flask again.
r Opsi )' (c-introduced and further λμ hours [
After shaking the mountain, the catalyst 'f! - Removed solvent from door to door. The resulting residue was subjected to chromatography (silica gel,
Gasolino/diethyl ether solution] to obtain a colorless oil (2.tO%).

(Elemental analysis; Actual values: O, A O, 2: H, Ri, Ri: N
,IA,/.

Theoretical value for 015H24FN30 0, A
O, 7: I(, Ta, j: N.

/ 6. λ %) IR knee 32jO, Jri! 10,X2
10, X200.

//10,1010. riIAo, 71.0°410cm
.

N1vla t ta OMH
z: CD0t31 0J Hiroshi (JH, t.

J=AHz+,/,0/(H,s);/,01-/,
A (fH, mJ: JJj (/H, sl: Hiroshi 3 Otsu (21
-1, sJ: Hiroshi, lA I 2 H, d q.

J = u 7 and I Hz J: 7. Rij
(/H, sl:!, / 7 (/H, s I: Mass spectrum m/z 2jf (M+Hl.

lI &, X12. /73', l'3 (I00%).

Practical row/7 This practical row contains 2,2-dimethyl-/-chloro-3-hydroxy-3-pentyl-gu(/, 2.≠-triazol-7-yl-1-butane (Table 1, compound/16, 2/I
This compound was prepared from the corresponding pro-zergyl alcohol using the general method of Example 11/6. The product was yellow, gummy and contained the following properties: IR, 32!0, 19!0. X310. X210°X2
00. //410,1020,7!0゜trOcm-' NMa (5'□MHz:O
DOt31 0J! (jH,t.

J=AjHz l :/,/ (AH,d, J=l
A,! rHz J: / −/ j / −JC
A H+ ml: / -J-/ -A C-2H
, m l : j , -26(/H, b r l :
3,nir (,2H,s l ;!,j♂(koH,sJ
near, Pff(/H,sJ:f,,2(/H,sJ:2 mass spectra 17hirofM+[-17°202,X
97. X12. ♂3 (700%I.

Table 1 shows the compound 17.2,2-dimethyl-3-hydroxy-3-(IA-chlorophthyl)
-≠-(/, 2. Shows the production of Hiro-triazole-/-ylbutan.

Step 1 Add n-butyllithium (/, AM hexa/Tsuba) to a bath solution of toluenesulfonyl/-futhyne (7,≠y, 33 mmol) in anhydrous detrahydrofura/(30+nl) at -50°C under a nitrogen atmosphere. 11;i, 2/ml
J was added and the reaction mixture was stirred for -1520 minutes. Chlorotitanium triisopropoxide (/, OM hexane solution 33 me J'l: was added slowly and the mixture was stirred for 2 J min. Tetrahydrofuran (≠O-')
The triazolilbina colon (j, Of, J 0-
) was added, the mixture was gradually warmed to room temperature, the reaction mixture was quenched with ammonium salt solution and extracted with ethyl acetate. The crude product was column chromatographed on silica gel, dried over anhydrous ~4g5OJ and evaporated to give a yellow oil (391km).
Diluted with ethyl acetate (t10-to%) in gasoline,
Toluene sulfol derivative (≠, 3flk white crystalline solid (melting point O-ta λ'C) is obtained in step λ ethanol (j (7 mSI), step / product (lr
, 2. To a solution of 100 g of palladium on carbon (0,1 J moles) was added and the mixture was heated at ≠0° C. under hydrogen pressure of &0 psi overnight with the addition of 5" g of water. The reaction mixture was filtered and Part F was concentrated in vacuo to give a pale yellow gum. Column chromatography on silica gel was performed using diethyl ether (jO) in gasoline.
-100%) Then ethyl acetate in gasoline (!-Hiroo
%) to give the toluenesulfonate derivative of the title compound as a yellow gum (0.27?+).

Step 3 Product of step λ (0.2t 9 , 0.6 mmol)
, lithium salt (0,/V, 2.4+!mi IJ morn and lj) methyl sulfoxide (/(I) ml mixture f 100 °C (bath IL41-C3 time 1i; l 71 [
Once heated, the reaction mixture was completely cooled and then fractionated between ethyl acetate and water.

The aqueous phase was further extracted with ethyl acetate and the combined organic extracts were washed with saturated sodium bicarbonate solution, water and then brine, dried over anhydrous magnesium sulfate and evaporated to dryness to yield the title compound. (0, l r f
NMR obtained as a completely yellow oil (ODO451j
70 Mtotz) δ:O, Tano(ri l(, g l
: /, /-/, jt (Hiroshi H, Kombuchrekus).

/,j! IλH, Co/Bookex); 3.00
(/H,s): 3.32 (2H.

L): u, 20 (uH, s l ; 7. J' 2 (
/ll,s J:za,Og(/ll,s):I
R(filmM 3300-30!0,
312! ; 、 /! 10 cm-' real row/represent real row is 2,2-dimethyl-3-hydroxy-J-(
2-methyl-/-pe/thyl/-yl)-≠-(/,
2. Production of Hiroshi-triazol-7-yl)-butane (Table 1, Compound A/≠) is shown.

Anhydrous tetrahydrofuran (20 ml of anhydrous tetrahydrofuran) was added to a stirred suspension of magnesium flakes (o, try, r 7 mmol) and/crystalline iodine in anhydrous tetrahydrofuran (20 ml of anhydrous tetrahydrofuran) at room temperature under a nitrogen atmosphere. Copromopentane (3,! P, ,! 3 mmol)
The mixture was heated under reflux for 5 minutes, cooled to room temperature, and unreacted magnesium was transferred to the dropping port by tilting. The solution was heated to -70°C under a nitrogen atmosphere.
Steel bromide in tetrahydro7rane (20 ml I)
Dimethyl sulfide complex (4t, j?, 2u mi IJ
The reaction mixture consisted of an epoxide (2,0 y, / / mmol) derived from triazolylbinacoro/triazolylvinacoro (2,2 mol) and the mixture was stirred for 75 minutes. The reaction mixture was added dropwise to f!
, cooled and extracted with ethyl acetate; the combined organic extracts were washed with dilute ammonia solution, water and Bly/;
The crude product, dried over MgSO4 and evaporated to dryness, was subjected to column chromatography on silica gel and eluted with diethyl ether (20-10 chino) in gasoline to give the title compound (2,2 r l i yellow Obtained as an oil in the form of diastereomers.

NM^(0f)Ca3, 270 M)(z lδ: 0
．． 6-○, Ri (7H, Complex +; 0.7 Otsu, O17g (Ta)
I, ,2 singlets/,0-/,za(A
H.

Complex flow: 3.0jt-L//(/ If
, 2 singlets, ≠, 2≠(2H, quartets I
Near, Riot(/H,s), J',/A(/H,s11 Hydrogen analysis: 0,4827N30: Theoretical value 0, A A,
J A: H, / 0.7 hiro; N, / lj I
Actual measured value: O, AC≠0: H, / 0. ♂
! ;N, / i ivy person m/e N o 0M ++ , 2J I +
/Riotsu, /7/, /lf, /! ;0°/2t, 109,
13 Implementation dag.

2.2-Dimethyl-3-hydroquino-3-(coethylbutyl)-gu(/,,2.≠-triazol-7-yl)-buta/(Table 1, compound A;/j) It was prepared using the general method of J/R.

The compound was a yellow oil and had the following properties: N'JR(CD0L5 + , -! 70 MHz
lδ: Q, Otsu♂ (J j-1, t); o, 7 J
'(j[1°[);0. I/(Ito(, complex) : (7,5' t (DeH, S j', /, Or
(λH, complex IS/,, 2 (2H, complex]; Hahiro (/H, complex)', /, t≠(/H, dd)
:J,,2/(/H,sl;!,,2 4Z
(=2 H, q]; 7.fJ (/
fl.

s ); Do, / Do (/H,5JIFL(Film: 3700-3/jO,3/,20./60(
I7cm-'m/eNo. -(/,λ,t,t-triazole-/
-yl]-butane (Table 1, compound shop/A) is produced using the general method of Example A, and the product is a yellow oil (a mixture of noastereomers) with the following properties. NM [(, (0DO43, λ70vlHzlo, 6-
o, ri (6H, complex]; /, 0 , /, 0
Hiro (RiH, 21 solid singlet); 1. ltar/, 1yoH, complex J", /,!;-/, Ir<koH,
Ko7fu V ivy, < ): J, A O, jj': 44
゜(zo, H,; two singlets j; Hiroshi, 36(2H, 2
7. quadruplet; ri3 (/H, s J: r, /F (/
II + s IIP, (Film I 3t!0
-J/! 0,3/jOcm-'m/eNoM,
/riA, /7/ /lr, /! θ, 10ri.

Tata, rr Elemental analysis C14H27N30 theoretical value 0, Al,, 3 A; H, / 0.7≠: N
, / ijzachi actual measurement value 0 , & A, Otori: H, / OA
t 4 :N, /i 6 % Example 22 This run shows the preparation of the toluene sulfonate salt of compound '1'/1&2 of Table 1.

Compound *JA2 (0,/j?, 0.63 mmol, p-toluenesulfonic acid (0,/24'?Iz ethyl acetate (jmtl) and ethanol (trntJ) were heated under reflux for 6 hours to form a reaction mixture. Concentration under vacuum, trituration with diethyl ether and evaporation to dryness gave the toluenesulfonate salt as a low melting off-white solid.

N'1Ji(, (CDO43, -270MHz)(
:1. J'(JH,t): 0Jlr(5'H,s
l: /, 0-Hahiro (It ■, Complex]; λ, 3
AC3H,sl:≠,J-(koIT,ql near,,2(,2H,di near,7&(,2toI,dl:and,≠(/11.s):10./(/H , bsJ implementation sequence,
23 In Table 1, the orthooxalate of the compound nico was prepared in the same manner as in Example 20. Raw 5i, the object had the following properties: N'vHt(ODO/,3, =270 MHz
] :0JI3H,t); 0.91+9 t1
．． s):/, 0- /, A (f ) t, complex j; ≠ j (, 2H, ql: A, ri6 (Hiroshi 14. Very wide singlet); 7. Do♂(/)l, sl;r, Jj(
/H, sJ Practical Row 2 (Table 1) Dodecylbenzene sulfonate from (E Hardware Shop λ) was prepared in the same manner as in Practical Row 20. The product had the following caustic properties. .270'Ahz ) oJ (
/ o H, complex no; O0 ri (ri @, s
l:/,-! (,2,!l−[complex l:
/j(buto(,complex);a,!(,2H,q l: 7./yo(
21(, d l Near J(2H, d I :1.21(
/ H+ s l : TaJj(/[(, sl
A "selection test for whole plant parts" was conducted for the compounds listed in Table 1. The terminology is "partial 5Creen" and "enzyme 5Creen".
This means that a wide variety selection test is performed on all parts of the plant. The above-mentioned compound vI was used to test the plant growth regulating activity on plants of 72 rod species and various plant growth effects related to plant growth regulation. l! Table 4 shows the types of plants used in the selection test and the growth stage of the leaves when the chemicals were sprayed. Each chemical was sprayed with a track sprayer.
After spraying N applied at a concentration of ≠kq/ha using a Teejet nozzle and a spray volume of 4LOOOpprn<tooot/ha, the plants were kept in a greenhouse at a daytime temperature of 2. !r℃7 night temperature W
Grown here at °C. Supplemental light irradiation (from a mercury vapor lamp) was performed as necessary to obtain an irradiation time of 76 hours. As an exception, the grains wheat and barley are subject to daytime temperatures/
Grow at J-tA'c/night m degrees l/-73°C.

2 to 2 depending on the age of the plant (time of yearJ)
After leaving the plants in a greenhouse for 3 weeks, the plants were visually observed to examine their morphological characteristics, and then plants to which no chemicals were applied were used as controls. The test results are shown in Table ■.

Example 26 Another whole plant part subject selection test (2) was conducted for the compounds numbered as shown in Table 1. All of these compounds were used to test the plant growth regulating activity on three types of plants, and various plant growth effects related to plant growth regulation.

Methodology Table V shows the kind of plants used in this study and the stage of leaves when sprayed with chemicals. Each drug was sprayed using a trunk sprayer and an 8SrooaE (Teejet) nozzle.
'1000 ppm (spout 9i1 volume 1k '0''Z
The plants were grown in a greenhouse at daytime temperatures of 22°C and nighttime temperatures of 22°C. , if necessary to obtain an irradiation time of 76 hours (minimum/lt hour) - supplementary light irradiation (from a mercury vapor lamp).

As an exception, the grains wheat and barley were grown at a daytime temperature of 16°C and a nighttime temperature of 3°C. Depending on the plant type and time of year, the plants were allowed to grow after being left in the greenhouse for a week. Morphological signs were examined by visual observation. Plant #A to which no drug was applied was used as a control. The test results are shown in Table ■.

Symbols: R = Growth retardation G = Nibbling fruit A = Top damage T = Tillering or lateral parting ■ = Interlingual length 9 = Reduction in interlaminar length All effects / - Grade of J Evaluated at vending machine f/:, :1
=io ~304 λ = 37~t o Width 3 engineering 47 S-1004 Blank area II'' It means that the lt effect is less than i0%.

Example core Te5t) Test method In this test 381 plants, namely rice.

Next using spring barley and apples. The types and growth stages of these plants are 4th.
7t shown in the table, the test compound was sprayed over the entire surface (overall spray).
sp-ray)/000 pprnb and '1000 ppm (respectively at a field capacity of 100,011 kgf and 100,000 ppm/ha).

This spray provides a prerequisite for application to the leaves and roots in this test: i.e., this test determines the activity of the arsenic that acts on the leaves and roots.
Grow in paddy-like "pots" (-paddy): i.e. roots and lower parts of stems.

Water Gtl under conditions corresponding to when planted in water
C immersion friend. Spring barley and apples were grown in 1 inch pots. For these plants, for spring barley and rice, ligulg' at the top about 2 g days after treatment.
) and, for apples, the height to the top of the plant approximately 2 to 8 years after treatment. The test results are shown in Tables (1) to (X).

ioo of each test compound in each plant.

The nine results obtained in the test with 1 ppm and tA 000 ppm application were compared with the height of the plants described above in the test without application of the test compound (blank test) VC.

The name of the decline of the official was shown in the blank test due to the height of the plant dying.

Part ■ Table Decrease rate of senior officials in apple trees (compared to blank test) *100 ppm *2000 ppm Part ■
Reduction rate of height of front spring wheat (compared with blank test) *100 JOOOOppm pm Chapter X Reduction rate of height of front spring wheat (compared with blank test) Wood 100 ppm *2000 ppm Rigi's example is a European patent! -2 Hiroko Hiro issue details oath (gPJ
-, 2 Hiroshi 2 Hiroshi) and the compound of the present invention. Although a large number of compounds are included in this example, testing of the compounds was done in parallel (5ide-b
y-side) was not carried out.

The compounds compared in this example are the compounds tested in one of the tests. These tests are screening tests V) and V) whose methods are described in Example 5 and λ≦, respectively.

Comparison of cross-selection tests between compounds (across-s
Clean comparison) is the comparison between the total growth retardation caused by the test compound (i.e., the retardation score recorded for each compound tested) compared to the total growth retardation caused by the standard compound in the selection test. This is done by expressing it as a Criteria for test performance and environmental factors are provided for standard drugs. These factors can be eliminated by expressing the activity of the test compound as a percentage of the activity of the standard compound. The same standard compound was used in every study; this compound was palc-obutrazoJ (growth regulator).
The results are shown in Tables X and XI.

Although this example generally shows that the compounds of the present invention are clearly superior as plant growth regulators, in order to examine their activity in more detail, a parallel comparative study was carried out in the following example. show. In these Examples, representative compounds described in the specification of EPjJ4Lλ are compared with representative compounds of the present invention.

Table Based on the total growth retardation dust, expressed in q.

gp,! 2≠Total growth retardation dust induced by the compound listed in Table 2 of the Specification of No. 2 (*Average of 8λ tests) In Examples Kota and 30 below, a selection test and an intermediate growth retardation test were carried out. A representative compound of the present invention was compared with a representative compound described by GPT Co., Ltd., and the results are shown below.

Example-22 Compound t*2. r and /2 (compounds of the present invention) and compounds A% B and 0 (compounds described in EPj-Hiroshiλhiro issue)
A whole plant part selection test was conducted on the following. The plant growth regulating activity on these plants was tested for various plant growth effects related to plant growth regulation. The structure of the test compound is shown in FIG.

Test Methodology The types of plants used in this test and the stage of leaves when the chemicals were sprayed are shown in Table V above.

Each drug is Traxgeler and S 8 r004AE.
(Teejet) using a nozzle, 47000 p.
pm (at a spray volume of 10001/ha,
Concentration of Hirokf/ha) and alms friends.

After spraying, the plants are kept in a greenhouse at a temperature of 21°C/night temperature Z2.
Grow at ℃. If necessary to obtain a 76-hour irradiation time, supplementary irradiation (from mercury vapor Lang) should be carried out, with the exception of the cereals wheat and barley, which have a daytime temperature of 16
℃/night temperature t3℃.

After leaving the plants in a greenhouse for 2 to 2 weeks depending on their age, the plants were visually observed to examine their morphological characteristics. Plants not treated with chemicals were used as controls.

The test results are shown in Table XIII.

H I Figure 1 Compound part λ H3 Compound compound ugliness magnetokinesis/2 H3 Xm table symbol: R = Growth retardation G = Niblining fruit A = Apex damage T = Tiller or side bulge = Interlingual or Reduction in intersegmental length All effects were evaluated visually on a scale of /-3: /2 lO
~30% Co=37~60% 3=6/~100% Blank spaces mean the effect is 10% or less.

Example 3Q Intermediate growth retardation test Test method Three types of plants were used in this test, namely rice.

Make sure to use spring barley and apples. The types and growth stages of these plants are shown in Table 4. The test compound is whole injection 9
1000p as (over;jllspray)
pm and Hiro 000ppm (respectively, / 000
In a field capacity of L/ha/~ and Hiro 1'
g/ha) was applied. This spray provides the ingredients to be applied to the leaves and roots in this test; i.e.
This test determines the activity of the compound on leaves and roots. Rice is Hiroi/Chi1 paddy-like flowerpot (ゝゝpad
dy //pot); ie.

The lower parts of the roots and stems were immersed in water under conditions corresponding to when planted in rice fields. Spring barley and apples were grown in Hiro inch flowerpots. For these plants, for spring barley and rice, the top Kokichi (I
The height to iguleJ was measured, and for apples, the brightness to the top of the plant was measured about 2 days after the treatment. The test results are shown in Tables XIV to W for each test compound f/000 ppm and 4L in each plant.
The results obtained in the test in which 000 ppm was applied were compared with the height of the above-mentioned plants in the test in which the test compound was not applied (blank test), and the percentage decrease in height was expressed as an ax with respect to the height of the plant in the blank test. Ta.

Chapter Xll/ Reduction rate of height of front apple tree (compared with blank test) Chapter XV Reduction rate of height of front rice (compared with blank test) Rock Comparison with blank test) Example 31 Test method Select young Red Delicious apple trees with uniform size and leaf width.
At the size stage, the plants were sprayed with the test compound using a tox sprayer.

The test compounds were applied as a total spray at / 000 ppm and 1,000 ppm (1Kf and 1,000 ppm in a field capacity of /QOQt/ha, respectively). The spray provides the ingredients to be applied to the leaves and roots in this test; ie.

This test determines the activity of the compound on leaves and roots. Apple trees are allowed to grow in a mixture of John Innes flower pot compost, lawn and sand in a ≠ inch flower pot. After treatment, the height to the top was determined 1 and 21 days after treatment. The results were compared with the blank test, and the rate of decrease in height was expressed as a percentage of the height of the plant in the blank test. The results obtained are shown in Table 1.

Table 1. Reduction rate of height of apple trees (comparison with blank test) Example 3-2 This example uses Compound 2 in Table 1 as a release agent for thinning of peaches. activity.

Test method: Select a homogeneous peach tree branch with 20 flowers. The test compound was applied to this branch at two different application rates.
It was sprayed at two different times. The application rate is 20 ppm/
OCD ppm and spray timing is i.

This was the time when the petals of the chinese petals fell (T/) and the length of the ovule reached rm. A repeated test of 1 treatment per day was conducted (i.e. 1% Hiromoto branches were used. The flower thinning effect was 1.
Evaluation was made by counting the number of flowers remaining on the branches during the period when hand-picking is usually done. The number of remaining flowers was dried and used as a blank test for comparison (F B
) are shown in the table along with the results.

*: Due to natural flower fall, the number of flowers will decrease compared to the original number of flowers.
The number of friends decreased from one to two.

A method of formulating the compounds of the present invention into compositions suitable for application is shown in Examples 33 to 3 below. All references in these examples are percentages by weight.

Example 3J The following components were mixed and the mixture was stirred until all the components were dissolved to prepare an emulsifiable concentrate in B111.
IO%FLONI(J I)N
P/J! %1 Aromasol'(' Arom
asol') HI O% Example 3 The first three components below were triturated in the presence of water and sodium acetate was added. After drying the resulting mixture, it is passed through a British standard sieve, size≠Hiroshi-1oo to obtain a particle size of the desired size. The following compounds were prepared: Compounds in Table 1! O% ant deis no sosol'('DjspL!rsolsu'l'
Jj% Umugi Synperonic〃NPj
/, 3% sodium acetate
23. ! Example 3j All of the following ingredients were ground together to prepare a powder formulation that was easily dispersible in liquids. Compounds of Table 1 173% Disnozesol T! Chi Shin Peronic #NX O,j Chi Whisper Cero 7 As'('0elJofas') Btoo
2% china clay GTY powder
Hiro 7. ! Example 36 After dissolving the active ingredient in attapulgite clay granules, the resulting solution was applied onto attapulgite clay granules. Jt foggy.

The solvent was then evaporated to give a granular composition: Compounds of Table 1! Thiatabalgite Granules Example 37 A seed dressing was prepared by mixing the following 3 Fiy: Compounds of Table 1 O% Mineral Oil
2
A powder for dispersion was prepared by mixing Example 3 with the active ingredient and Merck: Compounds of Table 1 j% Talc
Ta! Example 3 A flowable formulation was prepared by pouring the following ingredients into a bead barrel and suspending the ground mixture in water: Synperonic NP!/% water
Dispersible powder formulations were prepared by mixing the following ingredients and grinding the mixture until all ingredients were thoroughly mixed: Compounds of Table 1 -25% Allozole ( 'Aerosol') OT/B
j%1 Days Nog Sol〃A, 0.
! Chi clay 2? Tisilica 4tO% Example Gl Mix the following ingredients and then grind the mixture (Com
91 Dispersible powder formulations were prepared by milling with mjnuNon milυ: Compounds of Table 1 -! Chiari Parbanal/F (%pg几MINAL //JBX
/% Ant Dispasol'T
Polyvinylpyrrolidone 10% Nlica 25% Ceramic clay
31 Example 2 A dispersible powder formulation was prepared by mixing the following ingredients and pulverizing the mixture: Compounds in Table 1 2! Ax 1 Aerosol" OT/B 2% 1 Disnozesol A! Chi china clay 60 Descriptions of the various compositions and substances shown by trade name and trade name in the above examples are provided below.

■ Synperonic NP/J: Nonylphenol (Imol ethylene oxide (73 mole condensate) Aromazole H: Solvent mixture consisting of alkylbenzene ■ Dispasol T and AC: Sodium sulfate and formaldehyde-sodium naphthalene sulfonate condensation Mixture with 9 synperonic NPj: Nonylphenol (
Condensation product of Imol and 7talen oxide (!, jmol) Gasero7as IBt00: Sodium Calxymethyl cellulose thickener

Claims (1)

[Claims] General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is an alkyl group having 4 to 9 carbon atoms or an alkyl group having 3 to 8 carbon atoms. haloalkyl group or group -CH_2-C
H_2-Z (Z is an optionally substituted cycloalkyl or cycloalkenyl group containing 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl ring); R^2 is hydrogen or an alkyl group having 1 to 4 carbon atoms; and R^3 is a tert-butyl group optionally substituted with halogen] and stereoisomers thereof; and salts thereof;
Esters and metal complexes. 2, R^1 is a branched or straight chain alkyl group having 4 to 7 carbon atoms, a branched or straight chain mono-haloalkyl group having 3 to 6 carbon atoms, or a group -CH_2-CH_2-Z (Z is cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl group). 3. The triazole derivative according to claim 1 or 2, wherein R^2 is hydrogen or a methyl group. 4. The triazole derivative according to any one of claims 1 to 3, wherein R^3 is a tertiary butyl group optionally substituted with one fluorine, chlorine or bromine atom. 5, R^1 is an alkyl group having 4 to 9 carbon atoms; R^
2 is hydrogen or an alkyl group having 1 to 4 carbon atoms; R
The triazole derivative according to claim 1, wherein ^3 is a tertiary butyl group. 6, R^1 is the group -CH_2CH_2-Z, and Z is an optionally substituted cycloalkyl or cycloalkenyl group containing 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl ring; ;R^2 is hydrogen or an alkyl group having 1 to 4 carbon atoms; and R^2 is hydrogen or an alkyl group having 1 to 4 carbon atoms;
Claim 1, wherein 3 is a tertiary butyl group optionally substituted with one or more halogen atoms.
Triazole derivatives described in . 7. General formula (IIIa) or (IIIb): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IIIa)▲Mathematical formula,
There are chemical formulas, tables, etc. ▼ (IIIb) (In the formula, R^1 and R^3 have the meanings given below), respectively, with the general formula (IVa) or (IVb):
R^3M(IVa) R^1M(IVb) (wherein R^1 and R^3 have the meanings given below, and M is a metal), characterized by reacting with an organometallic compound of General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is an alkyl group having 4 to 9 carbon atoms, a haloalkyl group having 3 to 8 carbon atoms, or a group -CH_2 -C
H_2-Z (Z is an optionally substituted cycloalkyl or cycloalkenyl group containing 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl ring); R^2 is hydrogen; Yes; and R^3
is a tert-butyl group optionally substituted with a halogen. 8. General formula (V) or (VI): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (V) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (VI) (In the formula, R^1 and R^3 are It has the meaning below, and Ha
l is a halogen atom) and 1,2,4-triazole, using the 1,2,4-triazole in the form of its alkali metal salt in the presence of an acid binder or in a customary solvent. characterized by reacting with
General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is an alkyl group having 4 to 9 carbon atoms, a haloalkyl group having 3 to 8 carbon atoms, or a group -CH_2 -C
H_2-Z (Z is an optionally substituted cycloalkyl or cycloalkenyl group containing 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl ring); R^2 is hydrogen; Yes; and R^3
is a tert-butyl group optionally substituted with a halogen. 9. General formula (X I ): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula (
I ): ▲Mathematical formulas, chemical formulas, tables, etc. and is an optionally substituted cycloalkyl or cycloalkenyl group);
R^2 is hydrogen; and R^3 is a tert-butyl group optionally substituted with halogen. 10. General formula (I): ▲Mathematical formula, chemical formula, table, etc.▼(I) [In the formula, R^1 is an alkyl group having 4 to 9 carbon atoms or a haloalkyl group or group having 3 to 8 carbon atoms. -CH_2-C
H_2-Z (Z is an optionally substituted cycloalkyl or cycloalkenyl group containing 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl ring); R^2 is hydrogen or an alkyl group having 1 to 4 carbon atoms; and R^3 is a tert-butyl group optionally substituted with halogen] and stereoisomers thereof; and salts thereof;
A plant growth regulator composition containing an ester and a metal complex as active ingredients.