JPS595170A - Triazole compound, manufacture and fungicidal or plant growth regulant composition - 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 triazole compounds useful as fungicides,
A method for producing the compound, a fungicidal and plant growth regulating composition containing the compound, a method for preventing infection by 0α fungi using all of these, and a method for controlling the growth of plants using the same. 1 siri.

European Patent Application No. 7309g y-';
The following formula: [In the formula, IL' is 100=CI(-X,-(lmi0-X
or -0TT2-OH2X where Xt and Hl are alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, or optionally substituted aryl, aralkyl, aryloxy, alkyl or ti-heterofunctional group)
■ L21-1 alkyl, cycloalkyl (%J
is an aryl group substituted with
triazole and imidazole compounds of Ct or ON or OH3 (wherein rmo3 must be Hl, acetyl, alkyl, or alkynyl group; YU-N- or -0H-), and acid addition salts and metal complexes thereof is disclosed.

According to the present inventor's findings, a narrow range of f-hybrid compounds C11 and 1 of the above-mentioned broad and general group.
t) Have a high quality killing suahi 6 life f1'.

According to Akira Sororiki, the following formula (I): [In the formula, I1.I is i -OH=Cl-1-X or -C30-, R2 is a halophenyl group; 9r+): Z&YO0几3(IdanL)L'
ir, J, 1. (,7/L, is a kyl, alkenyl or alkynyl group)] and acid addition salts and gold eye complex salts thereof are provided.

The compounds of the present invention contain geometrically shaped isomers r, l; k. Such compounds are generally obtained in the form of isomeric mixtures. However, mixtures of ILs and other mixtures can be separated into individual isomers by methods known in the art.

When X is an alkyl group, it is a straight chain alkyl group containing 7 to 3 carbon atoms, such as methyl, ethyl, propyl, butyl and amyl groups. In other respects, i.e. for any reasonable R'', the alkyl group can be a straight-chain or branched alkyl group having /~, for example /~ carbon atoms; examples include methyl, ethyl , propyl (n- or in-propyl) and butyl groups (n-,
SeC.

iso- or t-butyl). Examples of suitable halogens as substituents on the phenyl ring when it is a R2 group are fluorine, chlorine or bromine. That is, I
t'' is 2-, , ?- or poly-chlorophenyl1.
x, y-also 1rj, 2. -dichlorophenyl, λ-
,, 3-Also 1d<t-fluoronenyl, λ, 41-difluorophenyl, '-1,3-Also pl tx -7'
Romophenyl 1. z-chloro-9-fluorophenyl or i, J:, 2-chloro-t-fluorophenyl groups can be used.

Preferably, 几2 is a group of chlorophenyl or dichlorophenyl.

According to the gist of Monbetsu, the present invention relates to the general formula (I)
C, where X is H or an O14 alkyl group; R2 is a cuchlorophenyl or Kotsgauge chlorophenyl group; and Z is OR'' (wherein R' idH).

In yet another preferred aspect, the present invention provides the general formula (I) (
provided that R2' is co, da, su, q-dichlorophenyl or difluorophenyl group).

Preferred compounds contain the following formulas: OH 1 and OH 1 Said salts are salts with inorganic acids or Ii acid, such as hydrochloric acid, nitric acid, sulfuric acid, acetic acid, gutluenesulfonic acid or oxalic acid. Get 9.

The metal chain ring is suitably a complex salt containing copper, zinc, manganese or iron as the total metal chain.

The complex salt has the following formula: [where 几1 and 几2, 7. and Y￥i as described above, M is a gold frame, A is animene (1+Q is a chloride ion, a bromine ion, an iodine ion, a nitrate ion, a sulfate ion, or a fumophosphate ion), nI/J ', , 2 or g, y is an integer of O or /~/, 2, and mf is an integer corresponding to the egg value].

The FJ Th of the compounds of the present invention is shown below. These compounds are compared to the following formula: In the table above, the compounds mentioned above are new and therefore they form part of the invention as such.

The compound of the present invention represented by the general formula (I) is represented by the following formula (II) or (
■): R2几2 (II) (ill) [In the formula, R1, B2 and Z Lti ii + s, as described above,
Hal is a halogen atom (preferably i- is chlorine or η is bromine atom). In the presence of an acid binder or in a convenient solvent in the form of an alkali metal salt / , , 2
It can be produced by reacting with 4-triazole or imidazole.

The compound of general formula (II) or (7) is prepared in a convenient solvent such as acetonitrile, methanol, ethanol or dimethylform (7), sodium salt of triazole or imidazole (the salt of ξ is hydrogen f). Either hysodium or sodium methoxide f3:/,
2. It is suitable to react the compound by adding it to a triazole or imidazole at a temperature of 20 to 700°C. Product t:j-reaction crystal innie, -!
! ! 4r) can be simply isolated by dipping in water and recrystallizing the resulting solid from a convenient solvent.

The ;)-thyl (3-alkyl, etc.) of the present invention is formed from a hydroxy compound by reacting the hydroxy compound with a suitable halide in the presence of a suitable base.

General formula (II) wherein each of R1 and R2 is as described above
The compounds are novel and useful intermediates and as such form part of the present invention. The compound is prepared by adding dimethylsulfonium methylide (JAO8,/4J) using a method described in the literature to prepare a suitable compound of the following formula (): .

gll, p. 77♂2) or dimethyloxosulfonium methylide (JAO8,/91.
! ;.

17, /, 33.3 ~ /,? By reacting with (page J4)! , 1. Make II and do 1.

The following formula (V): (wherein R2 and It can be formed by

Compound 16 can also be formed by a Wissochig reaction between an aldehyde of the following structural formula (■) and a phosphorane of the following structural formula (■). (1) (in the formula (2) - and X are as described above).

The above phosphorane (■) can be converted to the above formula (■) by treatment with a strong base such as n-butyllithium in a suitable solvent such as diether or tetrahydrofuran by standard methods in the literature.
■ Spun from the phosphonium salt of 1). The aldehydes (Vl) mentioned above can be formed by methods described in the literature.

The above formula (II) and (Ill'') (However, LZUOHT
, 6) of the general formula (IXa) or (]Xb): (IXa ) (IXb ) (where It
', 2 and hat are as described above) are expressed by the following formula (Xa) or 1j (xb):

R'M (Xa) R”M (Xb)
[In the formula, IL' and l (2 is as described above, M is a metal, Q1 is preferably lithium, but can be sodium or magnesium (when M is magnesium, the organometallic compound is In practice IL'Mg h a + or R2
Mghhl)] by reacting with an organometallic compound! ] can be prepared. Jin's reaction is compound 11 (Ill)
alone or compound (II) alone or 11 compounds (]II and (
11). Specified metal compound (Xa)
is preferably reacted with compound (IXb) at low temperature.

Compounds of the general formulas (IX) and (X) may be formed by methods described in the literature. For example, the acetylene alcohol of the present invention can be formed by any of the following λ reaction schemes.

Reaction Scheme 1 α-haloketo/ of the formula (D(b) shown below (where 14" is as described above) is reacted with the formula (X) (where X is as described above) in an inert atmosphere at a low temperature. The product is worked up by reacting the appropriate acetylene gold with the S salt and quenching with a proton donor.

11 ■ R2-0-( to OX 0 [I2 Azole (Xll) Reaction IA formula
XIV) with the sulfur ylide and all the resulting epoxides are reacted with a suitable azolyl salt.

( ) L2- (j -0 miO- It can be formed by reacting an uncomplexed compound with a metal salt.

The olefinic azolyl alcohol in which R' is 0H=O) (-X and R2 is the above-mentioned p[1〈 It may be formed by the reduction of acetylene thread azolite alcohol (XI) with hydrogen in the presence of metal hydride reagents, especially lithium aluminum hydrogen, in a suitable solvent such as ether or dihydrofuran.

Reaction scheme θ 01
) is prepared according to the present invention.

The compounds, salts and metal complexes of the present invention are effective fungicides, particularly against the following diseases: Rice blast disease (-P-irlculara, ogz
3-t3-Human wheat rust (Pupc, in, j-a
r-ecoB-dita), (1': ucciqj-
a! 4t, j i j-o-kai O) and other rusts, barley rust (Puccinja qo-rd, ej
), (iu, c-ci-n-ja st
rust and other host plants such as coffee, apple, vegetable and ornamental rust, powdery mildew of barley and wheat (Ery
, 5iphe gr.
, 1-pe, , l-), apple powdery mildew (Pod
-osp, ha-eraleuc9! r j+: ha)
and powdery mildew of grapes (Uncinulane-t,
atp-r), cereal Helminthosborium (He
l-min, thospor, lum sp, p, )
Rhynchosborium (R-h y n7cho-s2.o
ps-e-u, -do-c, e
-r-cosporella her-P”=trI-
C,ho,,5dq) Peanut katsunosen disease (0,e
,r-,cos,,po,,r-aarac-h
i-iIc-oja) and for example sugar beet 1. ? Nana and other kappan diseases of soybeans (4μ, gray mold of tomato, ichino, grapes and other host plants) black spot of apples (, Vesuysu) horses (shadow ails)
.

Some of the compounds of the invention also showed broad spectrum activity against molds in vitro. These compounds are responsible for various diseases after fruit harvest [e.g. green mold of oranges (1'en
It has activity against M. d□±atum), blue mold (Aenicales 1ium itallcum), and tansou disease (Dongjiesu L. musar tsui)].

Furthermore, some of the compounds of the present invention may be used to treat cereal Ginkgo biloba (Fus).
arium spp, “Kamahaftensis 5eptor”
la spp.

Tl1letia spp (i.e., wheat smut, seed-borne disease), cut±ago i
pp, Hey I-ynjp Lee-osporlum”
app+ and j+eudscere-o sd ha erp
otr±qhoides cotton white silk disease (3j+1zoc
tonlas35pnI) and rice sheath blight (Oo
rtlcium s, aaakil) as a seed dressing agent.

The compounds of the present invention can move apically in plant tissues from below in an apical direction. Furthermore, the compounds of the present invention may be sufficiently volatile to be effective in the gas phase against fungi on plants.

The compounds of the present invention can also be used for industrial purposes (agricultural purposes).
It may be useful as an agent, for example, in preventing mold attack of wood, hides, hides, and especially paints.

The compounds of the invention are also useful in the treatment of candidiasis and human dermatophyte infections.

The compounds of the invention and their derivatives as described above also have plant growth regulating activity.

The plant growth regulating effect of the compounds of the invention is manifested, for example, by an inhibitory or inhibiting effect on the growth of the developing parts of woody plants and leathery monocotyledonous and dicotyledonous plants. Such suppression or inhibition may occur, for example, if a reduction in stem height results in other advantages such as stem strengthening, thickening and shortening, segmental shortening, increased protruding root formation and more upright stem and leaf orientation. Useful for peanuts, cereals such as wheat and barley, rapeseed oil, rapeseed, field pulses, sunflowers, potatoes and soybeans, where the risk of lodging can be reduced with or without these effects, and also to increase the amount of fertilizer. It can be applied in Suppressing the growth of woody plants is useful for regulating undergrowth of power lines and the like. Compounds that induce inhibition or inhibition are also useful in altering the stalk growth of sugarcane, thereby increasing the sugar concentration in sugarcane at harvest; in sugarcane flowering and ripening can be inhibited by the application of said compounds. Can be adjusted. Stunting of groundnuts can aid harvest.

Retarding the growth of grasses helps maintain the lawn. Examples of suitable grasses include Augustine grass (St. and Poa).
(e.g. Boa curvature platens) can inhibit the growth of grasses without significant phytotoxic effects and without adversely affecting the appearance (color) of the grasses; This makes them attractive for use in ornamental lawns and meadow edges. The compounds described above may also have an effect on the flowering of flower heads in grasses, for example. The compounds of the invention are also present in grasses. The growth of weeds can be suppressed; examples of such weeds are great [such as Oyperus sp.
) and dicotyledonous rushes (e.g. daisies, plantains, willows, stag beetles, thistles, scampi and grasshoppers).The growth of non-crop plants (e.g. weeds or surface plants) can be retarded, thus It helps maintain farm and field crops.In orchards, especially those suffering from soil erosion,
- The presence of grass growing on the surface is essential. However, excessive grass growth requires substantial maintenance. Compounds of the invention may be useful in this situation.

In some cases, these compounds can restrict the growth of plants without killing them (plant death results in soil erosion); at the same time, the degree of competition for nutrients and water by grasses is reduced. This can result in increased fruit yields. In some cases, some grasses can be suppressed over others; this selectivity preferentially suppresses the growth of undesirable plant species. It may be useful, for example, to improve the properties of lawns.

Such growth inhibition may also be useful for reducing the size of ornamental plants, houseplants, garden plants, and nursery plants, such as daisies, chrysanthemums, carnations, tulips, and daffodils.

As mentioned above, the compounds of the present invention can be used to completely inhibit the growth of woody plants. This property can be used to adjust the shape of hedges or fruit trees (e.g. apples, pears, cherries, etc.).
(peaches, grapes, etc.) f: The need for shaping or pruning can be reduced. Some conifers are not significantly inhibited in growth by the compounds of the present invention, and therefore, the compounds of the present invention may be useful in controlling the growth of undesirable persimmons in conifer nurseries.

Plant growth regulation effects may manifest themselves in an increase in crop yield as described above; or, in orchards or other crops, in the ability to increase fruit yield, pod yield, and grain yield. obtain.

For potatoes, it may be possible to control 4 casts in the field and to suppress germination in storage.

Other plant growth regulating effects produced by the compounds of the invention include changes within leaves and leaf shape! ? ＠Changes, both of which can increase light capture and utilization, and promotion of tillering in monocots. Improved light capture is important for all major world crops such as wheat, barley, etc. It has value in rice, corn, soybean, sugar beet, potato, plantation crops and orchard crops. Intraleaf modification effects are useful, for example, to change the leaf orientation of potato crops, thereby It provides light rays and causes an increase in photosynthesis and an increase in tuber weight.By increasing tillering of monocot crops (e.g. rice),
The number of flowering buds per unit area can be increased, thereby increasing the total grain yield of such crops.

Furthermore, better regulation and modification of plant taxonomic stage relationships will
It is possible to increase the number of flowering buds per unit area, especially in cereals such as wheat, barley, cotton and corn, both in the growth and propagation stages of monocotyledonous and dicotyledonous cultivation. and the grain size distribution within the ear can be modified in a manner that increases yield. In the treatment of rice plants or crops, the compounds of the invention may be applied, for example, as granules or granular compositions, eg slow-release granules, to seedbeds, supplementary waters and other similar cultivation sites and media. In lawns, especially in lawns that provide comfort, increased tillering can give a denser lawn, which can increase abrasion resilience; as well as increased yield and better quality of lintels, e.g. It can provide improved digestibility and good taste.

Treatment of plants with compounds of the present invention can provide leaves with a darker green color. In dicotyledonous plants such as soybeans and cotton, there can be promotion of lateral buds.

The compounds of the invention can suppress or at least delay flowering of sugar beet (which can increase sugar yield) or otherwise alter the flowering pattern of a number of other crops. The compounds can also reduce sugar beet size without significantly reducing sugar yield, which can lead to increased planting density.

Similarly, other root vegetables (e.g. capra, swede)
e), Manzaard, American zephyr, sugar beet, yam and capra) can also increase the planting density.

The compounds of the present invention can be useful in restricting the growth of developing parts of cotton plants, thereby resulting in increased cotton yields. Crop yields can be increased by improving the harvest index (ie, yield harvested as a percentage of total dry matter produced) by changing the distribution of dry matter. This applies to all the above-mentioned root and pod crops, trees, plantation and orchard crops.

Compounds of the invention may be useful in making plants resistant to external stimuli. This is because the compounds can retard germination, shorten stem height, and delay flowering in plants grown from seeds; these properties are common in regions with significant snow cover in winter. may be useful in preventing frost damage. This is because the treated plants then remain under a blanket of snow during cold weather. Furthermore, the compounds may cause early seedling resistance or cold damage resistance in plants.

When applied as seed treatments at low rates, the compounds can have a growth-promoting effect on plants.

In carrying out the plant growth regulating methods of the present invention, the amount of compound applied to regulate plant growth will depend on a number of factors, including the particular compound chosen to be used and the amount of compound applied to regulate plant growth. Depends on the type of plant. However, generally 0. /~izkg, preferably 0. An application rate of /~j kq is used. With slow-release granules of biodegradable polymers, application rates of ~109/l hectare are possible; however, lower application rates can be developed with electric spray technology. However, even application rates within these ranges can result in undesirable phytotoxic effects on plants. Routine testing may be necessary to determine the best application rate for a particular compound suitable for any particular purpose.

Although the compounds of the present invention can be used as such for fungicidal or plant growth regulating purposes, it is more convenient to formulate them into compositions for such uses. That is, the present invention also provides a fungicidal or plant growth regulating composition comprising the compound of general formula (1) as described above or its salt, metal complex ether or ester, and optionally a carrier or diluent. be.

The present invention also provides a method for controlling fungi, which comprises applying a compound as described above, or a salt, metal complex salt, ether or ester thereof, to a plant, a seed of a plant, or the site of a plant or a seed.

The invention also provides a method for regulating plant growth, which comprises applying a compound as described above, or a salt, metal complex, ether or ester thereof, to the plant, to the seeds of the plant or to the site of the plant or the seeds.

The compounds, salts, metal complexes, ethers and esters of the invention can be applied in a number of ways, for example directly to the leaves of plants in formulated or unformulated form, , spraying or dispersing the compounds, salts, metal complexes, ethers and esters, with or without application to the seeds or to the plants, trees or other medium in which they are growing or to be planted. Alternatively, the compounds, salts, metal complexes, ethers and esters can be applied as vapors or as slow-release granules. It can be applied to any part of the plant, tree or tree, for example to the leaves, stems, branches or roots, or to the soil surrounding the roots, or before sowing the seeds. or to the soil in general, to water in paddy fields, or to hydroponic systems.

The compounds of the invention can also be injected into plants or trees and can also be sprayed onto plants using electric spray technology.

As used herein, the term "plant" includes seedlings, candies and trees. Further, the fungicidal method of the present invention includes preventive treatment, preventive protection treatment, preventive treatment, and eradication and eradication treatment.

The compounds of the invention are preferably used in the form of compositions for horticultural and horticultural purposes. The type of composition used in this case will depend on the particular purpose being met.

The composition of the invention comprises an active ingredient and a solid diluent or carrier, such as kaolin, bentonite, diatomaceous earth (kles).
dolomite, calcium carbonate, talc, powdered magnesia, fuller's earth, gypsum, herite earth, diatomaceous earth
) and fillers such as china clay. Such granules may be preformed granules suitable for application to soil without post-treatment. These granules may be formed by impregnating pellets of filler with the active ingredient or by pelletizing a mixture of active ingredient and powdered filler. Compositions for seed dressings may, for example, include agents (e.g. mineral oil) to help the composition adhere to the seeds; alternatively, they may be treated with organic solvents (e.g. N-methylpyrrolidone or dimethylformamide). Active ingredients can be formulated for seed dressing purposes.

The composition of the invention also includes: It can be in the form of a dispersible powder, granule or particulate containing a wetting agent to facilitate the dispersion of the powder or particles in a liquid. Such powders or particles may also contain fillers and suspending agents.

One or more active ingredients are dissolved in an organic solvent optionally containing one or more wetting agents, dispersing agents or emulsifiers, and the mixture thus obtained is then similarly dissolved in one or more wetting agents. Aqueous dispersions or emulsions can be prepared by adding to water which may contain agents, dispersants or emulsifiers. Suitable organic solvents include ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, xylene, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers such as λ-ethoxyethanol and λ- Cytoxyethanol).

The compositions of the invention to be used as spray liquids can also be in the form of an aerosol, in which the preparation is placed in a container under pressure in the presence of a propellant, for example fluorotrichloromethane or dichlorodifluoromethane.

The compounds of this invention can be mixed in the dry state with artificial mixtures to form compositions suitable for generating smoke containing the active ingredient compounds in a confined space.

Alternatively, the compounds of the invention can be used in microencapsulated form. The compounds can also be formulated into biodegradable polymeric compositions to provide slow, controlled release of the active substance.

By including suitable additives, such as those for improving the dispersion, adhesion and amphoteric properties of the treated surfaces, different compositions can be better adapted to the intended application.

The compounds of the invention can be used in mixtures with fertilizers (eg nitrogen-containing, potassium-containing or phosphorus-containing fertilizers). Preferred are compositions containing the compound of the present invention, for example, consisting only of fine soot fertilizer particles coated with the compound. Suitably, such granules contain the active ingredient compound gold at a level of 12J.

The present invention also provides a fertilizer composition containing the compound of general formula (1) or a salt or metal complex thereof.

The compositions of the invention may also be in the form of solutions for use as dipping or spraying solutions, generally in the presence of seven or more surfactants such as wetting agents, dispersing agents, emulsifying agents or suspending agents. or an aqueous dispersion or emulsion containing the active ingredient; or a spray composition of the type suitable for use in electric spray technology.

The above agents may be cationic, anionic or non-ionic. Suitable cationic agents are quaternary ammonium compounds such as cetyltrimethylammonium bromide.

Suitable anionic agents include soaps, salts of aliphatic monoesters of sulfuric acid (e.g. sodium lauryl sulfate and salts of sulfonated aromatic compounds (e.g. sodium dodecylbenzenesulfonate, sodium lignosulfonate, calcium or ammonium), Butylnaphthalene sulfonate, and a mixture of the sodium salts of diisozorobyl- and triinpropyl-naphthalene sulfonic acids.

! Suitable non-ionic agents are the condensation products of fatty alcohols such as oleyl alcohol or cetyl alcohol with ethylene oxide, or the condensation products of ethylene oxide with alkylphenols such as octylphenol or nonylphenol and octylfuresol. Other nonionic agents are partial esters derived from long chain fatty acids and hexitol anhydride, condensation products of said partial esters with ethylene oxide, and lecithin.

Suitable suspending agents include hydrocolloids such as polyvinylpyrrolidone and sodium carboxymethylcellulose.
, and vegetable gums such as gum arabic and gum tragacanth.

Compositions for use as aqueous dispersions or emulsions are generally supplied in the form of concentrates containing high proportions of seven or more active ingredients. The concentrate is diluted with water before use. These concentrates often survive storage for long periods of time;
After such storage, aqueous solutions can be diluted with water to form aqueous solutions that are homogeneous long enough to enable their application by conventional powered spray equipment. Concentrates may conveniently contain up to 5% by weight of one or more active ingredients, suitably from 10 to 0% by weight of active ingredient. These concentrates suitably contain an organic acid (for example an alkaryl or aryl sulfonic acid such as xylene sulfonic acid or F-tecylbenzenesulfonic acid). This is because the presence of such organic acids can increase the solubility of one or more active ingredients soluble in the polar solvents often used in the concentrate. It is also suitable for the concentrate to contain a high proportion of surfactants, so that a sufficiently stable emulsion in water is obtained. After dilution to form an aqueous solvent, such solutions may contain varying amounts of one or more active ingredients depending on the intended purpose, but may include o,oos wt.% or o,oi wt.%. Aqueous solutions containing up to 10% by weight of one or more active ingredients may be used.

The compositions of the invention may also contain seven or more other biologically active compounds, such as compounds with similar or complementary fungicidal or plant growth activity or plant growth regulating activity, herbicidal activity or insecticidal activity. It can also contain active compounds.

The other fungicidal compound is, for example, 5eptorla.

Gibberella and Helmlnthospor
It can be a compound capable of controlling diseases of ears of grains (eg, wheat) such as P. ium spp, seeds and soil-borne diseases of grapes, downy mildew and powdery mildew, and powdery mildew and scab of apples. Mixtures of these fungicides may have a wider range of activity than the compound of general formula (1) alone; furthermore, the other fungicides may be synergistic with the fungicidal activity of the compound of general formula (1). It can have an effect. Examples of said other fungicidal compounds are imazalil, benomyl, calgindazim, thiophenate-methyl, cabtafor,
Kacitan, sulfur, triforin, dobumorph, tridemorph, virazofos, furaraxyl, ethyrimol, tecnazene, dimethylimole, bubilimate, chlorothalonil, vinclozolin, procymidone, iprodione, metalaxyl, forcetyl aluminum, carboxin,
oxycarboxin, fenarimol, nuarimol,
Fenflam, metofloxane, nitrotal-isopropyl, triadimethone, thiabendazole, ellidiazole, triadimenol, pyroxazole, dithianone, binabacryl, chinomethionate, guazatine, dodine, fentin acetate, fentin hydroxide, dinocap, folpet, dichlorofluanid, citarimphos, Kitazine, cycloheximide, dicloprazole, dithiocarbamate, copper compounds, mercury compounds, /-(,2-cyano-methoxyiminoacetyl)-3-ethyl urea, fenapanil, ofrace, propiconazole, etaconazole and hyfuenpropemorph It is.

The compound of general formula (1) can be mixed with soil, peat or other root media to protect plants from seed-borne diseases, soil-borne diseases or diseases caused by leaf fungi. do.

Suitable insecticides are bilimol, clonetone, dimethoate, methantox and formothion.

iii.Other plant growth regulating compounds may be used to inhibit the formation of weeds or seed heads, improve the degree of plant growth regulating activity or shelf life of the compound of general formula (1), and inhibit the formation of weeds or seed heads in less desirable plants. (for example, grasses), or make the compound of general formula (1) act more rapidly or more slowly as a growth regulator.

Some of these other plant growth regulators are herbicides.

Examples of suitable plant growth regulating compounds that can be used synergistically in combination with the compounds of the present invention include gipperellin (e.g. GA,
. ≠
-1) or MC! P A ), substituted benzoic acids (e.g. triiodobenzoic acid), morphactin (e.g. chlorfluorecol), maleic hydrazide, glyphosate, glyphosine, long chain fatty alcohols and fatty acids,
Dikeglax, fluoridamide, mefluidide, substituted quaternary ammonium and phosphonium compounds (e.g. chlormequat; chlorphonium or mepiquat chloride), ethephon, cal-4-tamide, methyl-J, 4-dichloroanisate, daminodipa aslam, abscisin p
(abscisic acid), inhirimor s
' (≠−chlorophenylhuμ.

6-dimethyl-oxo/, 2-dihydropyridine-3-carzenic acid, hydroxybenzonite') # (Example i
bromoxynil), difenzocort, benzoylpropethyl, 3T4-)chloropicolinic acid, and technazene. Synergism is most likely to occur when used with the above-mentioned compounds, which are first class ammonium compounds, especially those marked with an asterisk (*).

The use of a compound of general formula (1) in combination with gipperellin can be useful when it is desired to reduce the plant growth regulating effect of the compound (e.g. when the compound is intended to be used as a fungicide). case). If said compounds are to be applied to the soil surrounding the plants or to the roots of the plants, the plant growth regulating effect of said compounds may also be reduced in some cases by using different species of phenoxybenzoic acids and their derivatives. The present invention is illustrated by the following example, where temperatures are given in °C.

Example 1 This example has the following chemical structure: 0)] 1 The production of a compound having the following will be explained.

/, 2,4t-) lyazole (i,s'ri2) suspended in dry dimethylformamide (DMF) (7j-)) IJum (/, 329. SO in oil
Add the mixture little by little to the stirred suspension of [Synthetic Dispersion]. To the completed reaction mixture, add chlorohydrin (prepared as described below) in dry DMFC (10 ml) a, O2 in small portions to the above stirred solution, and then stir for 3 to 3 hours.
cvc heating (at which time all starting materials have disappeared from the gas-liquid chromatography (GLO) Ic).

The mixture is cooled, poured into water and extracted three times with ether.

The ethereal extract is washed with water, dried over magnesium sulphate and evaporated. This produces a schizam and crystallizes it into a cream powder (2, 2, 2, 2, m, p-13 to s°C).
Make it.

NMIL(ODOts)δθ, ri0(t, JH)/,
6 (sextet)

Ko ■ (), Ko, 13 (t9.2H), Hiroshi, 7.2 (dl
/H)%”, za♂(d,iH).

jβ(7(bs, OH), 7.co2(dd.

iH),"y, Hiro6(,3,tH),7,7!(d,i
H), 7. ra (!I, tH), r, ko (s, iH)
.

/R (nujo-h) 3200° λkoJ (7 (weak), -1 The following formula used in the above reaction: The chlorohydrin is prepared as follows.

l-Butyl lithium (dissolved in hexane/JM solution), 7 stnl of l-pentyne (dried DMF-2011 I/IC dissolved in 3,0
．． Add dropwise to the stirred cooled solution of 1). After the addition is complete, the clear solution is stirred at -71rC for 7. Stir for a minute.

Dry tetrahydrofluoride (THF) (J7ffi7 and K fc2,2) was added while maintaining the temperature below -t,r'C.
'.

Add (4/-)IJ dichlorocetophenone (S, Or) dropwise. The reaction is monitored by G L O during the addition and the addition of acetophenone is stopped when no more acetophenone is consumed. After stirring for an additional 30 minutes, the reaction was poured into water and extracted with ether. The ether extract is washed with water, dried, and evaporated to a yellow liquid (
S, jt) is obtained.

This compound was found to be purer than NM f' and 0LOK.

NM mouth, (ODOts) δt, o(t, 3H), t, r
s (+heavy ring.

iH) λ, λμ(t, 12H), J,! 6 (Hatake, OH), 3.rij<d, 2H)bF, /ri(
d, iH), 7.30 (d d.

tH), 7,4cO (d, iH) 7Jt (d
, iH) IR (liquid film) 3300 (strong) 1.2230 (
weak)/'ffi ''-' Example λ This example describes the preparation of the compound AF of Table 1 having the following formula:

Lithium aluminum hydride <5 itq)t, pentynyltriazole (2'mt) dissolved in dry ether (2'mt)
Add in small portions to the stirred solution of 1111M in Example 1). After the addition is complete, heat the mixture to reflux, and
Monitor from t, ovr. After refluxing for a total of 56 hours and adding 100q of T, jAtH4 separately, all the raw materials were consumed and disappeared. Cool the reaction and 100
It is very carefully poured into 12- of water and 12- of diluted hydrochloric acid, and extracted with ether.

The ethereal extract is washed with water, dried and evaporated. The residue is flash chromatographed on silica gel, eluting with 2:2 methylene chloride/methanol.

The product is isolated as clear and crystallized by rubbing with ether/petroleum fractions. The resulting white powder (
, 200 Misaki) has a melting point of ~j°C.

NMR (ODCIL3) δ0. It (electric, 3H), i,
3t (heavy ring.

+2H), 2.03 (Q12H)% Hiro, 70 (d, IH
), 3.60-6.0 (m, IH), t, 10 (d, I
H), 7.2K (dd.

/l (Huff, Fj (d, IH), 7,7Jr (d, I
H), 7. J'f (s, IH), J', /J (s,
/II) Example 3 The following compound is prepared by a method similar to that described in Example 1 and II with the physical properties described below. (t, 3H), Ko,
tlr (q, 2H), g, 7.2 (d, IH), Hiroshi,
riO(d, /l(),j,J(7(s,OH),7.3
0 (d d.

tH), 7. l2 (d, IH), 7.1 (d, IH),
7. rij(s, IH), ff, koj(s+1H) If'L(nujol)j, 200. Mu2FO (weak)
Down-1mpt t22-30'Q (white solid) 0
1 '□H NMn (ODOL3) 0. ? Ko(1, JH), λ,
Oj (j heavy ring.

, 2H), P, A 4' (d, IH) 3.00 (
*,OH),! ,06 (d,'H)+! , A O-
6,04' (m, / f(), 4.(7,+(d
, /)L),7. /g (dd, IH), 7.3 F (
d + 'H) b'' and (d, IH) 7.76
(s, IH),y,0O(s,IH)IR(nujorun3//0(yn-”rrlptlOter/
/θ℃ (lump-like) white crystal) N M R, (Or)
O/, 3) 0.1 Hiroshi (t, J I-I)
, i,io −10g.

(m, 4'H Ha,!, /F(t, 2H), <z, 7<z
(a, IH) b ”, ri,! (d.

/H)%j,zaO(s,OH),7.30(ad,I
H), 7. za6('+'t()+7,rii<(I+,I
H), g,! , 2 (a, IH) IR (Nujol) 3070.2JlO (weak). -1□、t zaj
-4'℃ (white crystal) 01 0r-1 NMR, C0DO13) 0J7 (t, jH), i
, or-i, t.

(m, 4'H), 1. ri0-. 2. ), θ(m, -2
H), <zjx(d, jH), μ, 7(7(s, OH)
, j, 06cd.

jH),! , ju-6.0 (m, jH), 6, oλ (d
, jH), 7. /j(dd.

jH), 7. A (d, tH), 7.6g (d, jH),
7. f(7(s,jH)za,'7(sl/H) IR, (Nujol) 307θtan-1 mpt 6g-6r℃ (white powder crystal) Example Hiromoto Example shows a compound having the following formula: This explains the manufacturing process.

Step l ♂Nyl Magnesium Bromide (3,7gt in magnesium shavings of AP and 33-g dry TI-IF)
(formed from vinyl bromide) was added dropwise with a dropper to a stirred solution of dichlorophenasilchloride 17 (j, z t ) dissolved in dry ether (33d, ) under argen. Add. The rate of addition is adjusted to obtain a mild reflux. Thirty minutes after the addition was complete, the reaction was cooled and poured into saturated ammonium chloride. The aqueous layer is extracted twice with ether and the organic extracts are combined, dried and evaporated to give an oil (F,4'?).

N　M　[(, According to the analysis, the following formula: showed the presence of chlorohydrin and small amounts of raw materials.

This material was used in the next step without making an NMR, (CD
Cl2), 2. riA(d,/)I), ,3.
/2 (d, jH).

It, 90-j, JO (m, +2H), j, Aθ-5,
ri0 (m, /l(), 7./0-7+60(m
+ ” H) IFL (liquid film) 33!0 (bs) stage λ Preparation of a compound having the following formula: (

Placed in dry DMF ('m/)/, 2. u-) Riazole (,2j t ) was added to a stirred suspension of hydrogenated) IJum (i, re) of a 50% dispersion in oil, which was washed out of the oil before use, suspended in dry DMF (/j ml). Add dropwise to the suspension. The turbidity reaches the outer edge of the AOC.

After the addition is complete, the solution is stirred for 30 minutes at room temperature.

The chlorohydrin/ from step l reactant (≠, Hiro?) placed in dry DMF (j me ) is added rapidly and the mixture is! Heat to 17 hours and then set up at room temperature overnight. The mixture is poured into water and extracted three times with ether. The ether extract is washed with water, dried and evaporated to give a dark oil (Il,Of). This oil was flash chromatographed, eluting with ethyl acetate, and the desired product was isolated as a brown oil, which crystallized by rubbing with an ether/petroleum fraction. j j f,
m, p, f J''' to obtain 0°C.

NMFL (ODOL,) Il, 7! -4,70 (m
, jl-1), 3.70 (dd, /H), 7. Hiro 4t (
dd, Il(), 7.40(d, /H), Otsurij(
d.

/H), r, or (s, iH), r, -2t(
II/H) IR(nujol) νJ/20cm=” (s) EXAMPLE This example describes the preparation of compound JA of Table 3.

Step 1 Preparation of an epoxide with the following formula: ) Completely dry acetylene gas is bubbled into dry THF (21 ml) at -7rC until the /f is dissolved.

Artane is then introduced, and n-butyllithium (dissolved in hexane, AM solution, F) is then added dropwise while maintaining the temperature below -6°C. Once the addition is complete, gradually add the goodichlorophenacyl chloride (j, Of) l into the dry TIIF (107) while maintaining the temperature between -70°C and -7j'crC. After the addition is complete, the mixture is stirred for 30 minutes and then warmed to room temperature overnight. The resulting brown solution is added to an aqueous ammonium chloride solution. The organic layer is separated, dried and evaporated to give a brown oil which is distilled (at 10.0
3113). The liquid crystallizes and becomes a solid (), F
t.

m, p, F (7-4t u °C).

NMR (0DOLs) 2.62 (s, /H
Habei70 (d, /)l), V,ri6 (d, /H
), t,i A (s,tH Hough,j,2(d
d, /H)% Otsu 4'J' (d.

iH), "y, ri4 (d, /H), 7Jj"
＋”')b ”'I1')I) I n, (Nujol) 3.26! Confucianism-1j/, 2
0 (yH' (weak) step! Preparation of a compound with the following formula: /,, 2. Gutriazole (0, Vzaf) was placed in dry DMF (/jd) Sodium hydride (jo coefficient dispersion in oil 0, j F f
) to form the anion. After the addition is complete, the mixture is stirred at room temperature for 30 minutes. Dry DME'
The epoxide (i,o r ) from the reaction of step 1 containing (/jm/) K is slowly added dropwise and the mixture is then heated for so'CVca time.

After standing overnight at room temperature, it was poured into a VCC bath solution and extracted with ether. Drying and evaporation of the extract gave a brown oil which was purified by flash chromatography eluting with ethyl acetate to give a brown oil which crystallized by rubbing with ether to give a light brown powder IT1. p/
Obtain ~/3/°C (0,j2"l).

NM day, (a D azs) -2, J
6 (s, /H), J, 7 0 (d,
Il(), 3.36(d, /H Hough, / 0-7j O
(m, JH) IR (liquid film) 3JOOcrn” (strong) -2/
-20cTn-'' (weak) Example 6 An emulsion is formed by mixing the following ingredients and stirring the mixture until all ingredients are dissolved.

Compound of Example 1 lθ-related ethylene dichloride 1′ Hiroθ-related calcium dodecylbenzenesulfonate j
%"Lubrol JL 10% [Aromasol jH3!%" Example 7 A composition in the form of particles readily dispersible in a liquid, e.g. The resulting mixture is dried through a British standard mesh sieve, with dimensions FF to lθO.
to obtain the desired particle size.

Compound of example jo% "Dispersol JT Jj%" Luprole JAPN
j/,,f% sodium acetate
, 23.5% Example g All of the following ingredients are ground together to produce a powder composition that is easily dispersible in liquids.

Compound of Example 3 Fj% "Dysnomysol" 1゛! % [Rezabol JNX O1j [Cerophas Jf3600 2% Sodium Acetate ≠7.j%] Example Dissolve the active ingredient in a solvent, spray the resulting liquid onto china clay granules, then evaporate the solvent to form the granular composition. Compound of Example G to be produced: 5% china clay fine grains
11 Example t.

A composition suitable for use as a seed dressing is prepared by mixing the following three ingredients: Compound of Example 1 50% mineral oil
λ Ware Ceramic Clay ″
■Example// υsanmai is produced by mixing the active ingredient with talc.

Compound of Example - 5% Tal Rita S Example 1 The ingredients listed below were ground in a Dahl mill and then dispersed (OoO
l) Compound of Example 3 to make the composition
lo staff “Jisunozozoru” T lO
#+"Lubrol JAPNj 7% Water Example 13 Example of preparing a dispersible powder composition by mixing the ingredients listed below with each other and then grinding the mixture until all are thoroughly mixed. Hiroshi's Compound 25 [Aerosol J
OT/B 2'ly [Dispersol J
A, O, 5% china clay rr% silica g θ Example/4' This example describes the production of a dispersible powder composition. The mixture is mixed in a separate tube and then ground in a fine grinding mill.

Compound of Example 1 -25% Normal JBX/% [Dispersol J'
l' jt% polyvinylpyrrolidone 70% silica
25% china clay 3%% Example is Compound of Example - 25% "Aerosol JO'l'/l" by mixing the ingredients listed below and then pulverizing the ingredients to form a dispersible powder. '(2nd Section ``Jinunozo-sol'' Aj Section Tou
Soil 6 I Example 6-is (in g, the proportions of a given component are by weight.

All compounds in Table 1 are formulated in the same manner as described in Examples 6-/jK.

Descriptions of the compositions or materials referred to above and represented by the various trade names and trade names are provided below.

Lubrol L: Condensate of dinonylphenol (1 mol) and ethylene oxide (/J mol) Aromazole H: Solvent mixture of alkylbenzenes Disnozosol T&AO: Condensate of sodium sulfate, formaldehyde, and sodium naphthalene sulfonate Mixture Luprole APNj: Nonylphenol (1 mol) Tonaphthalene oxide (j1j Molnt condensate Cellophas B6oo: Sodium carboxymethyl cellulose thickener +) 4'hole NX: Nonylphenol (1 mol) Condensate with toethylene oxide (j mol) Aerosol OT/B: Dioctylina sulfosuccinate IJum Perminal BX: Sodium alkylnaphthalene sulfonate Example/6 The compounds of the present invention are tested against diseases caused by various fungi that parasitize the leaves of plants. The technique used is as follows.

Plants were grown in Jeongin Os potting compost (A/or 2) in small diameter Hiroga pots. A layer of fine sand is provided at the bottom of the pot containing the dicots to facilitate uptake of the test compound by the roots of the plants.

The test compound was dissolved in dispersol (Dlspersol).
The test compound was formulated either by grinding in a bead mill with an aqueous T solution or as a solution by dissolving the test compound in acetone or acetone/ethanol and diluting it to the desired concentration immediately before use. For leaf diseases, a suspension with an active ingredient content of 1,100 pp is sprayed onto the soil. The exception to this is Botr disease (Botr).
ytis cinerea) downy mildew (Plasn
iopara viticola) and scabosis (Ve
This is a test for K.

The spray solution is applied to maximum leaf retention and the roots are immersed in such a way that the final concentration of active ingredient is approximately equivalent to 1 ppm of dry soil. If the spray solution is applied to the grains, 0.
Tween was added to give a final concentration of 0jt%.
en), 20 were added.

For most tests, the test compound is applied to the soil (roots) and leaves (by spray) one or two days before inoculating the plants with the disease. An exception is barley, in which case the plants are inoculated with the disease hours before treatment.

After the plants were inoculated with the disease, they were placed in an appropriate environment to allow infection and disease until the disease could be evaluated. The period from inoculation to disease evaluation was varied from 1 to 14 days depending on the type of disease and environment.

The disease suppression rate was recorded using the following grade: Kujihiro = No disease occurred 3 = Only a trace of contamination on untreated plants ~! Disease damage λ = 6-2j% disease on untreated plants L = 26-52% disease on untreated plants O = 60-100% disease on untreated plants The obtained results are shown in the table 2 below. .

Example 17 This example illustrates the plant growth regulating properties of compounds of the invention.

The test compounds are applied as a total spray of emulsion diluted to give the concentrations shown in Table 1. 7j of peat compost for plants,
Grow in 20 pots and spray at coleaf stage. The plant growth regulating effect was tested by the compounds tested. The growth inhibition rate is recorded in grades 1 to 3: l = θ ~ Jo inhibition rate Koni 31 ~ F 5% inhibition rate 3 = 7j% or higher inhibition rate L - No effect if there is no number of 3 represents.

The accompanying plant growth regulating properties are shown below. l-green A=tip growth effect T=tillering effect The results are shown in Table ■. The numbers indicate that the test compound is essentially inactive as an inhibitor.

Symbol AT of the test plant species in Table ■W 7 Agrostis tenuis (Agrostis
tenuis ) 00 Lettulus crest -a'tu
s) DA Dactyli glomereta (Dactyli
-+glomerata)LT Lettuce (Lact
uca 5aliva )8B Sugar beet (B
eta vulgaris ) To ) Mado
(Lycopersicum esculentum
)SY Glycine max OT Cotton (Oossypium hirsutum) MZ
) Maize (Zea mays )ww Winter wheat (Tri it icum aes ti Vuln)
) BR Taimu (Ilordeum vulgare)
Example 8 The compound of the present invention is tested against diseases on the leaves of plants. The technique used is as follows.

For all tests, plants were placed in small pots with a diameter of </6nm and treated with John Innes potting compost (1;
) Let your friends grow inside. Dicotyledonous flff vIJt Test by plant roots by placing a fine sand inlet at the bottom of the pot.
Promotes absorption of compound. The test compound can be formulated by grinding it in a bead mill with ligated Dispersol T solution, or it can be prepared as a solution by dissolving the test compound in acetone or acetone/ethanol and then diluting it to the desired concentration immediately before use. A test hit? Prescribed.

For all diseases, solution and suspension #1. Spray on the leaves or apply via the soil to the roots of the plant until maximum leaf retention is reached ([systemic permeation test)].

When the injection solution was applied to grain, 20 t of Tween was added to give a final concentration of O,OS%.

The test compound 5c was applied to leaves 7 days after inoculation.
Eradication eradication application using IC4 (1-erad J)
and for preventive protection hi (1-prot J) in which the test chemical is applied 2 days before inoculating the plant with the disease/loss Vi
It is. Disease inoculation is done by inoculating spores Nθ;j on the leaves of test plants.
By spraying the liquid? 'j. Next, place the plants in a suitable environment and enjoy! They were made to pay money and were infected with the disease until they were able to assess the damage. The period from inoculation to the time of disease evaluation was varied from t to /41 days depending on the type of disease and the environment.
The 1lJ rate is calculated using the grade of 1, from 3 to 96 diseases on untreated plants, with no disease occurring, and 3 to 96 diseases on untreated plants. The results shown in Table ■ below show that the untreated plants have a disease of 2t~, 99% disease 0 - the untreated f+7 has a disease of 0 to 100%.
rcospor8aracbidicola), apple powdery mildew (I'odospl+aera 1eu
cotrirba), apple scab (Ventur
ia inalgv; +Iis) and the lowest concentration (ppm) at which the grapevine drug can cause 8% or more of the total disease manifestation.
(i.e., a dosing range where control plants progress from grade 3 to grade 2). Powdery mildew of barley
In the test for cI'Tl1f1tp+)K, the results showed that the test drug was at least 1:[
(i.e. dosing range where control plants progress from grade Co/VC)
It is. Preventive protection (rprOtJ), eradication and eradication (['e
radJ) and whole body reference ('5ystJ). In this table the results are given in the form of presentation, for example: 0.0 1 0.0! is the concentration in ppm 0.0/p for the particular case in question.
PM and 0.0! It should be noted that the values are between ppm and ppm. The symbol "<" represents "less than" or "much lower than" a given specific concentration value, and ">" means "above" or "greater than" a given specific concentration value.

In the majority of comparisons, the compound A'n/~ of European time r'application peg/,? o lI-ga
The results of the previous 0C1 prove that the compounds Ai./~Jj are more active than the compounds Ai.s, -z and ftc I. The compound, 41. Not only are they more active against specific diseases, but their overall distribution of preventive H1 eradication and systemic rhopermeability properties over a targeted range makes the compounds highly effective against a wide range of agricultural fungi. Makes it useful as an agent.

■ (Continued) Table ■ (Continued) Continuation of page 1 Priority claim @ June 18, 1982 ■ United Kingdom (GB
)■8217693 @January 21, 1983■United Kingdom (GB)■8301679 0 Inventor Diana Marie Washington Berkshire Bratsquenell Jarrot Hill Research Station, United Kingdom (Street address and other information not shown)

Claims (1)

[Claims] Z Formula (I): [In the formula, 111 is -011=CII-X or (-, y -<
r,,,:c-X (However, if Xt is removed with ice water or straight 4d alkaline alcohol, R7'(1 is a halophenyl group, However) 1”)
-J-■], argyl, alkenyl? -J is an alkynyl group)] and its stereoisomeric 1'1 derivative; and acid addition salts and gold complex salts of II-. 2 几2 is 1'-,,? -also tr, L-chlorophenyl, no f/-also Czu, 2.4-, tsuku'10 phenyl, no. 3-51Ar'r,'l-fluorophenyl,'l
"-) fluorophenyl, λ-+J- or 1d<z-bromophenyl 1.:z-chloro-q-fluorophenyl 1.2-p-chloro-t-fluoro-phenyl or 1d, 2-
．． ．． The compound according to claim 1, wherein 3-4 is a methoxyphenyl group. 3, X is H spanning 01-1 alkyl group: R2 is t-
3. The compound according to claim 1 or 2, wherein chlorophenyl is a 1.2.4'-dichlorophenyl group, and 2 is 0R3 (however, 3 is H). Hiroshi The compound according to any one of claims 1 to 3, which is a compound having the following formula: Evening formula (II) or (ha (Ill) :1
) R2 几2 (II '') (Ill) (In the formula, 1t',) L2 and 2 have the following meanings, and X must be a halogen atom) Compound'?x A::4 Presence of a binder Below/, 1Ffa is reacted with a 2.41-triazole or imidazole or in the seven forms of its prucari metal salt in a convenient solvent/, , 2, 4-triazole or imidazole, Niyama: Tortoise [In the formula, R1 is 10H=OH-X or 0-C (where X is hydrogen or a straight-chain alkyl group)]: 11+2
is a halophenyl group! 11. Zoke OH3 (However, R”t
d H, alkyl, alkenyl or alkynyl group (al)]. A The following formula (■): R' [In the formula, I is also 1-0H=01iX-cross-C30-X (where X is hydrogen or a striped straight-chain alkyl group);
a triazole compound or a salt thereof;
Fungicides or plant growth containing metal complex salts, ethers or esters and optionally carriers or diluents? Section A Composition. Z The following formula (old or (ill): [In the formula, Bl is 10IL =Cl1-X or -(Ji-
x (provided that
f compound of H3 (where It3 is H, alkyl, alkenyl or alkynyl group), I [aA is a...gen atom] 0