Claims
- 1. A compound of any one of formulae I-VI ##STR5## where R.sup.1 is phenyl, C.sub.1-6 -alkyl-phenyl, halo-C.sub.1-6 -alkyl-phenyl, C.sub.1-6 -alkoxy-phenyl, halo-C.sub.1-6 -alkoxy-phenyl or nitrophenyl;
- R.sup.2 is 1-imidazolyl or 1,2,4-triazol-1-yl; and R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are each hydrogen, halo, C.sub.1-6 alkyl or C.sub.1-6 alkoxy.
- 2. A fungicidal composition which comprises a compound claimed in claim 1 in admixture with an agriculturally acceptable diluent or carrier.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 8612976 |
May 1986 |
GBX |
|
Parent Case Info
This is a division of application Ser. No. 054,191, filed May 26, 1987, now U.S. Pat. No. 4,772,613.
This invention concerns fungicidal heterocyclic derivatives, processes for their preparation and compositions containing them.
There are numerous examples of imidazole and triazole derivatives having fungicidal activity. Well known products include prochloraz (BP 1469772), triadimefon (BP 1364619) and propiconazole (BP 1522657). We have now found that compounds where an imidazole or triazole group is attached to a heterocycle have valuable fungicidal properties. We are not aware of published compounds of this type having such activity.
In one aspect, the invention provides a compound of any one of formulae I-VII ##STR2## where is a single or double bond;
In the groups R.sup.1, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, any alkyl or alkoxy moiety is preferably of 1 to 6 carbon atoms and any aryl moiety is preferably phenyl.
R.sup.1 is preferably phenyl, which may be substituted by one or more groups selected from halogen, alkyl (optionally substituted. e.g. by halogen, especially fluorine), alkoxy (optionllly substituted, e.g. by halogen and especially fluorine) or nitro. Particularly preferred groups which R.sup.1 may represent include phenyl, 4-chlorophenyl and 2,4-dichlorophenyl.
At least two, and preferbbly three or four, of R.sup.3 -R.sup.6 desirably represent hydrogen. Where only one of R.sup.3 -R.sup.6 is other than hydrogen, it is preferably R.sup.5. Examlles of groups which R.sup.3 -R.sup.6 may represent include chloro, bromo, iodo and methyl.
Preferred compounds are those of formula I.
The compounds of formulae I-V may be prepared by reaction of the corresponding compounds where R.sup.2 is halogen, usually chlorine, with 1,2,4-triazole or imidazole. The halo precursor compounds can be prepared in a variety of ways known in the art and as exemplified in the Examples. Some may be known compounds.
Compounds of formula VI can be prepared by reacting a compound of formula VIa ##STR3## with a compound of formula
The compound of formula VIa can be prepared by reacting a compound of formula VIb ##STR4## where Hal is a halogen atom such as bromine, with 1,2,4-triazole or imidazole.
Reactions with 1,2,4-triazole or imidazole are usually carried out under basic conditions.
The compounds of formulae I-II are fungicidal, possessing activity inter alia against a wide range of phytopathogenic fungi, particularly phycomycetes, deuteromycetes, ascomycetes and basidiomycetes orders, e.g. Powdery mildew (Erysiphe oraminis) on cereal crops such as wheat, barley, oats and rye and other cereal diseases such as glume blotch (Seotoria nodorum). leaf blotch (Rhynchosporium secalis), eyespot (Pseudocercosporella herpotrichoides), rusts (e.g. Puccinia graminis) and take-all (Gaeumannomyces graminis). Some compounds of the present invention can be used to control seed borne organisms such as bunt (Tilletia caries) on wheat, loose smut (Ustilago nuda and Ustilago hordei) on barley and oats, leaf spot (Pyrenophora avenae) on oats and leaf stripe (Pyrenophora graminis) on barley. The compounds can be used against powdery mildews of other crops, e.g. cucumber powdery mildew (E. cichoracearum), apple powdery mildew (Podosphaera leucotricha) and vine powdery mildew (Uncinula necator). They can also be applied to rice for control of rice blast (Pyricularia oryzae) and to horticultural crops such as apple trees for the control of apple scab (Venturia inaegualis).
In another aspect, therefore, the invention provides a method of combating fungi at a locus infested or liable to be infested therewith, which comprises applying to the locus an effective amount of one or more compounds of formulae I-VII.
The invention also provides a method of regulating the growth of plants which comprises applying to said plants a growth regulating amount of one or more compounds of formulae I-VII.
The present compounds are normally employed in the form of compositions containing a surface active agent and/or a carrier.
The compositions will normally be produced initially containing from 0.5 to 99%, preferably from 0.5 to 85%, and more usually from 10 to 50% by weight of the present compounds, which are diluted if necessary before application to the locus to be treated such that the concentration of active ingredient in the formulation applied is from 0.05 to 5% by weight.
The carrier may be water, in which case an organic solvent may also be present, though this is not usually employed. A flowable suspension concentrate may be formed by grinding the compound with water, a wetting agent and a suspending agent, e.g. xanthan gum.
The carrier may alternatively be a water immiscible organic solvent, e.g. a hydrocarbon which boils within the range 130.degree.-270.degree. C., e.g. xylene, in which the compound is dissolved or suspended. An emulsifiable concentrate containing a water immiscible solvent may be formed with a surface active agent so that the concentrate acts as a self-emulsifiable oil on admixture with water.
The carrier may alternatively be a water-miscible organic solvent e.g. 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, formamide or dimethylformamide.
The carrier may alternatively be a solid, which may be finely divided or granular. Examples of suitable solids are limestone, clays, sand, mica, chalk, attapulgite, diatomite, perlite, sepiolite, silicas, silicates, lignosulphonates and solid fertilizers. The carrier can be of natural or synthetic origin or can be modified natural material.
Wettable powders soluble or dispersible in water may be formed by admixing the compound in particulate form with a particulate carrier or spraying motten compound on to the particulate carrier, admixing a wetting agent and a dispersing agent and finely grinding the whole powder mixture.
The term `surface active agent` is used in the broad sense to include materials variously called emulsifying agents, dispersing agents and wetting agents. Such agents are well known in the art.
The surface active agents used may comprise anionic surface active agents, for example mono- or di-esters of phosphoric acid with a fatty alcohol ethoxylate, or salts of such esters, fatty alcohol sulphates such as sodium dodecyl sulphate, ethoxylated fatty alcohol sulphates, ethoxylated alkylphenol sulphates, lignin sulphates, petroleum sulphonates, alkylaryl sulphonates such as alkyl-benzene sulphonates or lower alkylnaphthalene sulphonates, salts of sulphonated naphthaleneformaldehyde condensates, salts of sulphonated phenolformaldehyde condensates, or more complex sulphonates such as the amide sulphonates e.g. the sulphonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulphosuccinates e.g. the sodium sulphonate of dioctyl succinate.
The surface active agents may also comprise non-ionic agents, for example condensation products or fatty acid esters, fatty alcohols, fatty acid amides or alkyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyn-4,7-diol, or ethoxylated acetylenic glycols.
The surface active agents may also comprise cationic agents, for example alkyl- and/or aryl-substituted quaternary ammonium compounds such as cetyl trimethylammonium bromide, or ethoxylated tertiary fatty amines.
Preferred surface active agents include ethoxylated fatty alcohol sulphates, lignin sulphonates, alkyl-aryl sulphonates, salts of sulphonated naphthaleneformaldehyde condensates, salts of sulphonated phenolformaldehyde condensates, sodium oleoyl N-methyltauride, dialkyl sulphosuccinates, alkyl phenol ethoxylates, and fatty alkyl ethoxylates.
The compounds of the invention may of course be used in conjunction with one or more further active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties. Alternatively the compounds of the invention can be used in sequence with the other active ingredient.
In the method of the invention the compound is generally applied to seeds, plants or their habitat. Thus, the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growrh of fungi which may attack seeds. When the soil is treated directly the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds. A suitable applications rate is within the range of from 0.05 to 20 kg per hectare, more preferably from 0.1 to 10 kg per hectare.
Alternatively the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as protective measure. In both such cases the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged. For cereal crops such as wheat, barley and oats it is often desirable to spray the lant at or before growth stage 5 although additional treatments by spraying when the plant is more mature can augment resistance to the growth or spread of fungi. The spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary. Sometimes, it is practicable to treat the roots of a plant before or during planting, for example, by dipping the roots in a suitable liquid or solid composition. When the active compound is applied directly to the plant a suitable rate of application is from 0.01 to 10 kg. per hectare, preferably from 0.05 to 5 kg per hectare.
US Referenced Citations (3)
| Number |
Name |
Date |
Kind |
|
4115097 |
Lang, Jr. et al. |
Sep 1978 |
|
|
4563455 |
Ueda et al. |
Jan 1986 |
|
|
4721670 |
Osada et al. |
Jan 1988 |
|
Divisions (1)
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Number |
Date |
Country |
| Parent |
054191 |
May 1987 |
|
Patent Grant
4853400
