Abstract:
There is provided a method for the control of phytopathogenic fungi and disease caused thereby which comprises contacting said fungi with a fungicidally effective amount of a benzophenone compound of formula I ##STR1## There are further provided benzophenone compounds of formula Ia which are useful as fungicidal agents and compositions useful for the protection of plants from the damaging effects of phytopathogenic fungi and fungal disease.

Description:
BACKGROUND OF THE INVENTION 
     Food production relies upon a variety of agricultural technologies to ensure the growing population&#39;s dietary needs remain affordable, nutritious and readily available on grocery store shelves. Fungicides are one of these agricultural technologies which are available to the world community. Fungicides are agrochemical compounds which shield crops and foods from fungus and fungal diseases. Crops and food are constantly threatened by a variety of fungal organisms, which, if left uncontrolled, can cause ruined crops and devastated harvests. 
     In particular, ascomycetes, the causative agent for powdery mildew diseases are an ever-present threat especially to cereal and fruit crops. However, applications of fungicidal agents at disease control rates can cause phytotoxic damage to the target plants. 
     Therefore it is an object of this invention to provide a method to control phytopathogenic fungus without causing concurrent phytotoxic damage to the host plant. 
     It is another object of this invention to provide an effective and safe method for the protection of important agronomic crops from the damage and loss caused by a phytopathogenic fungal infection and the disease caused thereby. 
     It is a further object of this invention to provide benzophenone fungicidal agents and fungicidal compositions comprising a benzophenone compound. 
     These and other objects and features of the invention will become apparent from the detailed description provided hereinbelow. 
     SUMMARY OF THE INVENTION 
     The present invention provides a method for the control of a phytopathogenic fungus or a disease caused thereby which comprises contacting said fungus with a fungicidally effective amount of a benzophenone compound of formula I ##STR2## wherein R 1  represents a halogen atom, an optionally substituted alkyl or alkoxy group, a cyano or a nitro group; m is 0 or an integer of 1, 2, 3 or 4; R 2  independently represents a halogen atom, an optionally substituted alkyl or alkoxy group, a nitro group or when R 1  and R 2  are attached to adjacent carbon atoms, R 1  and one R 2  may be taken together to represent --CH═CH--CH═CH-- or optionally substituted alkylene or oxyalkyleneoxy; R 3  represents hydrogen, halogen, an optionally substituted alkyl, alkoxy, alkenyl, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxy, hydroxy, nitro, or an optionally substituted amino group; R 4  represents a hydrogen atom or an optionally substituted alkyl or acyl group; R 5  represents a hydrogen, halogen, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, hydroxy, trialkylsilyloxy group, --ONa, --OK, --OC(O)R 7 , --OCHR 8  C(O)R 7 , --OC(O)NR 8  R 9 , --OS(O) 2  R 8 , --OS(O) 2  NR 8  R 9 , --OP (X 1 )(OR 8 )OR 9 , --OP(X 1 )(R 8 )R 9 , --S(O)R 8 , --S(O) 2  R 8 , or R 4  and R 5  may be taken together to represent an optionally substituted alkylene or alkyleneoxy chain; n is 0, or an integer of 1 or 2; R 6  independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkoxy, hydroxy, --OC(O)R 10  group, or when R5 and R6 are attached to adjacent carbon atoms, R 5  and one R 6  may be taken together to represent --CH═CH--CH═CH-- or an optionally substituted oxyalkyleneoxy chain; R 7  represents a hydrogen atom or an optionally substituted alkyl or alkoxy group; R 8 , R 9  and R 10  independently represent a hydrogen atom, an alkyl group, or R 8  and R 9  may be taken together to represent an alkylene chain optionally interrupted by an oxygen or nitrogen atom; X represents an oxygen atom, a sulphur atom or a group NOR; X 1  represents an oxygen or sulphur atom; Y represents an oxygen or sulphur atom or a sulphonyl or sulphinyl group; and R represents a hydrogen atom or an optionally substituted alkyl, aralkyl, aryl or acyl group. 
     The present invention also provides crop protection methods, fungicidal benzophenone compounds of formula Ia, methods of preparation of said benzophenone compounds and fungicidal compositions comprising at least one formula I or Ia compound and an agriculturally acceptable carrier. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     Huge economic losses have resulted from the devastation and damage of important agronomic and horticultural crops caused by fungal infection and infestation. Pest management strategies, field resistance, and virulent strains have all contributed to agriculturalists&#39; concerns for combatting phytopathogenic fungal disease. In particular, ascomycetes, the causative agents for powdery mildew diseases continues to be a serious concern in cereal crop and fruit production. Further, in a variety of fungicidal agent applications concomitant phytotoxic injury to the host plant may be observed. 
     It has now been found that benzophenone compounds of formula I are highly effective fungicidal agents and are particularly effective for controlling mildew diseases such as powdery mildew. Compounds of formula I useful in fungus control methods are those benzophenones having the structure ##STR3## wherein X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , m and n are described hereinabove. 
     Alkyl as a substituent or as a part of other substituents, such as alkoxy or alkylthio may be straight-chain or branched and may contain up to eighteen, preferably up to 14, and especially up to 10, carbon atoms, individual examples including: methyl, ethyl, propyl, butyl, pentyl, hexyl, etc. as well as their isomers such as isopropyl, isobutyl, tertiary-butyl, isopentyl, and the like. Lower alkyl or alkoxy groups have from 1 to 10 carbon atoms. A cycloalkyl moiety as a substituent or as a part of other substituents suitably contains from 3 to 10, preferably from 3 to 6, carbon atoms. An alkenyl or alkynyl group suitably has from 2 to 6, preferably from 2 to 4 chain members, for example, ethenyl, propenyl, allyl, butenyl and the like as well as for chains with more than one double bond such as pentadienyl and the like. An alkylene chain usefully has 1 to 5, preferably 1 to 4, members. 
     An acyl group is formally formed by the removal of hydroxyl from a carboxyl group, and is used herein to include formyl and optionally substituted alkylcarbonyl and arylcarbonyl groups. 
     A halogen atom represents fluorine, chlorine, bromine and iodine, preferably chlorine. Preferred haloalkyl moieties are difluoromethyl and trifluoromethyl. 
     Optionally substituted moieties may be unsubstituted or have from one up to the maximal chemically possible number of substituents. Optional substituents may be any of those customarily employed in the development of biocidal compounds, and/or the modification of such compounds to influence their activity, persistence, penetration and any other property. Specific examples of such substituents include halogen, especially fluorine, chlorine or bromine, phenyl, alkylphenyl, alkoxyphenyl, halophenyl, phenyloxy, nitro, cyano, acyl, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkoxy, carboxyl, amino, alkylamino, dialkylamino, cycloalkylamino, piperidyl, morpholinyl, carbamoyl, mono- or dialkylcarbamoyl, morpholinocarbonyl, trialkylsilyl and the like. Alkyl moieties of such optional substituents usefully have from 1 to 6 carbon atoms, preferably 1 or 2 carbon atoms. 
     The benzophenone compounds according to formula I are oils, gums, or, predominantly, crystalline solid materials and possess valuable fungicidal properties. For example, they can be used in agriculture, or related fields such as horticulture and viticulture, for the control of phytopathogenic fungi, especially ascomycetes, and powdery mildew disease such as Erysiphe graminis, Podosphaera leucotricha, Uncinula necator and the like. Said benzophenone compounds possess a high fungicidal activity within a wide concentration range and may be used in agriculture without harmful phytotoxic effects. 
     Preferred formula I compounds useful in the method of invention are those in which R 1  represents a halogen atom or an optionally substituted alkyl or alkoxy group; m is 0 or an integer of 1, 2 or 3; and R 2  independently represents a halogen atom or an optionally substituted alkyl or alkoxy group; or R 1  R 2  together represent --CH═CH--CH═CH-- or alkylene; R 3  represents a halogen atom, an optionally substituted alkyl, alkenyl, alkylthio or alkylsulphonyl group, a nitro group, or an optionally substituted amino group; R 5  represents a hydrogen atom, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy or alkylthio group, a hydroxy group, a trialkylsilyloxy group, or a --OC(O)R 7 , --OCHR 8  C(O)R 7 , --OC(O)NR 8  R 9 , --OS(O) 2   R   8  or --OS(O) 2  NR 8  R 9  group; or R 4  and R 5  together represent an optionally substituted alkyleneoxy chain; n is 0 or the integer 1; R 6  represents an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl or cycloalkoxy group or a --OC(O)R 10  group; R 7  represents a hydrogen atom or an alkyl or alkoxy group; X represents an oxygen atom or an NOR group; and R represents a hydrogen atom or an optionally substituted alkyl group. 
     Good control of phytopathogenic fungi is obtained with a fungicidally effective amount of a compound of formula I wherein R 1  represents a halogen atom or an optionally substituted lower alkyl group; m is an integer of 1 or 3; R 2  independently represents a halogen atom or an optionally substituted lower alkyl group; R 3  represents a halogen atom, an optionally substituted alkyl or alkenyl group, or an optionally substituted amino group; R 5  represents an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy or alkylthio group or R 4  and R 5  may be taken together to represent an optionally substituted alkyleneoxy chain; n is 0 or the integer 1; R 6  represents an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl or cycloalkoxy group or a --OC(O)R 10  group; R 7  represents an alkyl or alkoxy group; X represents an oxygen atom or NOR group; Y represents an oxygen atom; and R represents hydrogen or C 1  -C 4  alkyl. 
     Especially preferred are those formula I compounds in which R 1  represents a halogen atom or C 1  -C 4  alkyl group; R 2  independently represents a halogen atom or C 1  -C 4  alkyl group; R 3  represents a halogen atom or an optionally substituted C 1  -C 4  alkyl group; R 4  represents an optionally substituted C 1  -C 4  alkyl group; R 5  represents an optionally substituted lower alkyl, alkoxy, alkenyloxy, alkynyloxy or cycloalkoxy group; R 6  represents an optionally substituted C 1  -C 6  alkoxy, alkenyloxy, alkynyloxy or cyloalkoxy group 
     Effective control of phytopathogenic fungi may be achieved, for example, with a fungicidally effective amount of one or more of the following compounds: 
     2,3,5,6-tetramethyl-4&#39;,5&#39;,6&#39;-trimethoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone-O-methyloxime; 
     2,6-dichloro-5&#39;-t-butoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;,6&#39;-di-n-butoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2&#39;-allyloxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2&#39;-benzyloxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2&#39;-butoxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2&#39;-cyclohexylmethoxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2&#39;-cyclopentyloxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2,6-dichloro-2&#39;,3&#39;,4&#39;-trimethoxy-6&#39;-methylbenzophenone; 
     2,6-dichloro-2&#39;-ethoxy-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2,6-dichloro-2-heptyloxy-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2,6-dichloro-2-hexyloxy-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone; 
     2,6-dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-(2-methoxy-ethoxy)-6&#39;-methylbenzophenone; 
     2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methyl-2&#39;-(3-methylbutoxy)benzophenone; 
     2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methyl-2&#39;-(prop-2-ynyloxy)benzophenone; 
     2,6-dichloro-3&#39;,4,-dimethoxy-6&#39;-methyl-2&#39;-pentyloxybenzophenone; 
     2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methyl-2&#39;-propoxybenzophenone; 
     2,6-dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-(3-methylbutoxy)benzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-(prop-2-ynyloxy)benzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-(octyloxy)benzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-(pentyloxy)benzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-propoxybenzophenone; 
     2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-trimethylsilanylmethoxybenzophenone; 
     2,6-dichloro-5&#39;-(1-ethyl-propoxy)-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-difluoromethoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-ethoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-heptyloxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-hexyloxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-isobutoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     2,6-dichloro-5&#39;-isopropoxy-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     5&#39;-butoxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     5&#39;-cyclohexylmethoxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     5&#39;-cyclohexyloxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     5&#39;-cyclopentyloxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methylbenzophenone; 
     5&#39;-cyclopropylmethoxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methylbenzophenone; or 
     5&#39;-decyloxy-2,6-dichloro-4&#39;-methoxy-2&#39;-methyl-benzophenone. 
     The present invention also provides benzophenone compounds of formula Ia ##STR4## wherein R 1  represents a halogen atom, an optionally substituted alkyl group or a cyano group; m is an integer of 2, 3 or 4; R 2  independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or when R 1  and R 2  are on adjacent carbon atoms, R 1  R 2  together represent --CH═CH--CH═CH-- or an optionally substituted alkylene or oxyalkyleneoxy group; R 3  represents a hydrogen or halogen atom, an optionally substituted alkyl, alkoxy, alkenyl, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxy, hydroxy, nitro, or an optionally substituted amino group; R 4  represents an optionally substituted alkyl or acyl group; R 5  represents a halogen atom, an optionally substituted alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, trialkylsilyloxy, --ONa, --OK, --OC(O)R 7 , --OCHR 8  C(O)R 7 , --OC(O)NR 8  R 9 , --OS(O) 2  R 8 , --OS(O) 2  NR 8  R 9 , --OP (X 1 ) (OR 8 )OR 9 , --OP(X 1 )(R 8 )R 9 , --S(O)R 8  or --S(O) 2  R 8  group or R 4  and R 5  may be taken together to represent an optionally substituted alkylene or alkyleneoxy chain; n is 0 or an integer of 1 or 2; R 6  independently represents an optionally substituted alkoxy group, a hydroxy group or a --OC(O)R 10  group when attached to adjacent carbon atoms, or R 5  and one R 6  may be taken together to represent --CH═CH--CH═CH-- or an optionally substituted oxyalkyleneoxy chain; R 7  represents a hydrogen atom or an optionally substituted alkyl or alkoxy group; R 8 , R 9  and R 10  independently represent a hydrogen atom or an alkyl group, or R 8  and R 9  may be taken together to represent an alkylene chain optionally interrupted by an oxygen or nitrogen atom; X represents an oxygen atom, a sulphur atom or an NOR group; X 1  represents an oxygen or sulphur atom; Y represents an oxygen or sulphur atom or a sulphonyl or sulphinyl group; and R represents a hydrogen atom or an optionally substituted, alkyl, aralkyl, aryl or acyl group, with the provisos that when X represents an oxygen or sulphur atom and: 
     (i) when R 1  represents a halogen atom, then (R 2 ) m  must be other than a halogen atom or no more than one alkyl or alkoxy group. 
     (ii) when R 1  represents an alkyl group, then R 2  must be other than alkyl; 
     (iii) when m is 1, then R 2  must be other than an alkoxy group; 
     (iv) when R 3  represents an alkenyl group, then R 3  cannot be substituted with an alkoxy or acyl group; 
     (v) when R 3  represents a haloalkyl group, then R 1  and R 2  must be other than a haloalkyl group; and 
     (vi) when Y represents an oxygen atom, then R 3  and R 5  must be other than a hydrogen atom and n must be 1 or 2. 
     The compounds having formula I (including those of formula Ia) may be prepared by a process which comprises reacting a compound of formula II ##STR5## with a compound of formula III ##STR6## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y, m and n are as hereinbefore defined and one of Z 1  and Z 2  represents a hydrogen atom and the other represents the group COCl; or one represents a magnesium halide group MgHal, wherein Hal is a halogen, preferably bromine or iodine, atom, and the other represents COCl or an aldehyde or nitrile group, followed in the last two cases by oxidation or hydrolysis, respectively, and optionally followed by further derivatization. 
     The starting materials of formula II and III are known products, and may themselves be prepared according to established methods or routine adaptations thereof. Substituents R 1  to R 9  which are not compatible with the selected reaction conditions may be introduced after formation of the benzophenone. They may be generated by known methods such as subsequent derivatization or substitution of a suitable group or by cleaving off a suitable protecting group. 
     When one of Z 1  and Z 2  is hydrogen and the other is COCl, the process is a Friedel Crafts reaction and is effected in the presence of a Lewis acid catalyst according to well-established procedures. Suitable catalysts include AlCl 3 , SnCl 4 , FeCl 3 , ZnCl 2 , TiCl 4 , SbCl 5  and BF 3 , which may be in a molar equivalent amount (based on the acyl chloride). However, it is also possible to use lesser amounts of catalyst at elevated temperatures, suitably under reflux temperatures, preferred catalysts under these conditions being FeCl 3 , I 2 , ZnCl 2 , iron, copper, strong sulphonic acids such as F 3  CSO 3  H, and acidic ion exchange resins such as Amberlyst® 15 and Nafion®. The reaction can be carried out in a solvent inert under the reaction conditions, for example ethylene or methylene chloride, benzene, decane or solvent mixtures, or in the absence of solvent, conveniently by employing one of the reactants in excess. 
     When the magnesium halide is reacted with a nitrile, i.e. the other group Z 1  or Z 2  represents CN, the immediate reaction product is an imine of formula IV: ##STR7## This intermediate is readily converted to the desired benzophenone derivatives of formula I wherein X is an oxygen atom by acid hydrolysis, suitably using mineral acids such as hydrochloric or sulphuric. 
     When magnesium halide is reacted with an aldehyde, i.e. the other group Z 1  or Z 2  represents CHO, the immediate reaction product is a tertiary alcohol of formula V: ##STR8## This formula V intermediate is readily converted to the desired benzophenone derivatives of formula I wherein X is an oxygen atom by oxidation, suitably using Mn(IV), Mn(VII), Ce(IV) or Cr(VI) derivatives, nitric acid or oxygen in the presence of a catalyst. 
     Certain oxime derivatives of formula I may be prepared by reacting the appropriately substituted nitrile oxide of formula VI with a suitable o-dimethoxybenzene of formula VII in the presence of aluminum chloride and an inert solvent to form an intermediate and hydrolyzing the intermediate in aqueous acid to give the desired product compounds of Ib. The reaction is shown in flow diagram I. ##STR9## 
     For compounds of formula Ib the substituents R 1 , R 2 , R 3 , R 6  and n are as defined hereinabove for formula I and Ia and m is an integer of 1, 2 or 3. The oximes of formula Ib may be O-alkylated or O-acylated using conventional alkylation and acylation techniques. 
     The substituents of the benzophenones produced according to the processes of the invention may be derivatized further according to established methods or routine adaptations thereof, such as hydrogenation, acylation or cleavage of ether bonds. 
     The formula Ia compounds of the invention are excellent fungicides, especially for the control of phytopathogenic fungi in agriculture or related fields. They are useful for the control of powdery mildew diseases, particularly of Erysiphe graminis, Podosphaera leucotricha or Uncinula necator. Due to excellent plant tolerance, the compounds may be used in all cultivation of plants where infection by the controllable fungi is not desired, e.g. small grain cereals, apples, vine. The absence of target crop phytotoxicity at fungus control rates is a feature of the present invention. 
     The present invention also provides a fungicidal composition which comprises a compound of formula I or Ia as defined hereinabove and an agriculturally acceptable carrier. Said composition may contain one or more compounds of the present invention. Preferably, at least one carrier in a composition according to the invention is a surface-active agent. For example, the composition may contain at least two carriers, at least one of which is a surface-active agent. 
     The compounds according to formula I or Ia may be applied as technical material, however, said compounds are preferably applied as a composition comprising, besides the formula I or Ia compounds, adjuvants and auxiliaries which are known for formulation purposes and are manufactured into e.g. emulsion concentrates, solutions which may be sprayed directly or diluted, diluted emulsions, wettable powders, soluble powders, dusts, granulates, microencapsulates by well-established procedures. The form of application such as spraying, atomizing, dispersing, pouring may be chosen like the compositions according to the desired objectives and the given circumstances. 
     It is contemplated, compounds of formula I or Ia may be formulated or applied, either alone or in combination, with one or more pesticides or plant growth regulants. Pesticides used in combination may be herbicides, insecticides or other fungicides or a combination thereof. When the formula I or Ia compounds are applied in combination with another pesticide or pesticides, they may be applied simultaneously or sequentially. Among the available fungicides which may be used in combination with formula I compounds are 4,6-dinitro-o-cresol, benalaxyl, benomyl, captafol, captan, carbendazim, chlorothalonil, copper, cymoxanil, dichlofluanid, dichlone, difenoconazole, dimethomorph, diniconzole, dinocap, dithianon, fenpiclonil, fenpropiomorph, hymaxazol, imazalil, iprodione, isoprothiolane, kasugamycin, mancozeb, mepronil, mercuric oxide, oxadixyl, oxolinic acid, penconazole, propineb, pyrifenox, thiabendazole, thiram, tolclofos-methyl, triadimefon, triflumizole, triforine validamycin A, vinclozolin, zineb, ziram, and the like. 
     The fungicidal compositions of the invention may be prepared by well-established procedures, e.g. intensive mixing and/or grinding of the active ingredients with other substances, such as fillers, solvents, solid carriers, and optionally surface-active compounds (tensides). 
     Solvents may be aromatic. hydrocarbons, preferably the fractions C 8  to C 12 , e.g. xylenes or xylene mixtures, substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, alcohols and glycols as well as their ethers and esters, e.g. ethanol, ethyleneglycol mono- and dimethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl 2-pyrrolidone, dimethyl sulphoxide, alkyl formamides, epoxidized vegetable oils, e.g. epoxidized coconut or soybean oil, water. 
     Solid carriers, which may be used for dusts or dispersible powders, may be mineral fillers, such as calcite, talc, kaolin, montmorillonite, attapulgite., The physical properties may be improved by addition of highly dispersed silica gel or highly dispersed polymers. 
     Carriers for granulates may be porous material, e.g. pumice, broken brick, sepiolite, bentonite, non-sorptive carriers may be calcite or sand. Additionally, a multitude of pre-granulated inorganic or organic materials may be used, such as dolomite or crushed plant residues. 
     Suitable surface-active substances may be non-ionogenic, anionic or cationic tensides with good dispersing, emulgating and wetting properties depending on the nature of the benzophenone compound to be formulated. Tensides may also mean mixtures of tensides. 
     Suitable tensides may be so-called water-soluble soaps as well as water-soluble synthetic surface-active compounds. Soaps usually are alkali, earth alkali or optionally substituted ammonium salts of higher fatty acids (C 10  -C 20 ), e.g. the sodium or potassium salts of oleic or stearic acid or of mixtures of natural fatty acids which are prepared, for example, from coconut or tallow oil. Furthermore, methyl-taurine salts of fatty acids may be used. However, so-called synthetic tensides are preferably used, especially fatty sulphonates, fatty sulphates, sulphonated benzimidazole derivatives or alkyl aryl sulphonates. The fatty sulphates or fatty sulphonates are normally used as alkali, earth alkali or optionally substituted ammonium salts and have an alkyl moiety of 8 to 22 carbon atoms, whereby alkyl also means the alkyl moiety of acyl residues, such as the sodium or calcium salt of lignin sulphonic acid, of sulphuric acid dodecylate or of a mixture of fatty alcohols prepared from natural fatty acids. This also includes the salts of sulphuric acid esters, sulphonic acids and adducts of fatty alcohols and ethylene oxide. The sulphonated benzimidazole derivatives preferably contain 2 sulphonic acid residues and a fatty acid residue with 8 to 22 carbon atoms. Alkyl aryl sulphonates are, for example, the sodium, calcium or triethyl ammonium salts of dodecyl benzene sulphonic acid, dibutyl naphthalene sulphonic acid or of a condensate of naphthalene sulphonic acid and formaldehyde. Furthermore, phosphates, such as the salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids, may be used. 
     Non-ionic tensides are preferably polyglycolether derivatives of aliphatic or cycloaliphatic alcohols, saturated or non-saturated fatty acids and alkylphenols, which have 3 to 10 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon residue and 6 to 18 carbon atoms in the alkyl residue of the alkyl phenols. Other suitable non-ionic tensides are the water-soluble, 20 to 250 ethylene glycol ether groups containing polyadducts of ethylene oxide and polypropylene glycol, ethylene diamino polypropylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms in the alkyl moiety, the substances normally contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples of non-ionic tensides are nonylphenol polyethoxy ethanols, castor oil polyglycol ether, polyadducts of ethylene oxide and polypropylene, tributyl phenoxy polyethoxy ethanol, polyethylene glycol, octyl phenoxy polyethoxy ethanol. Furthermore, fatty acid esters of polyoxy ethylene sorbitan, such as polyoxy ethylene sorbitan trioleate may be used. 
     Cationic tensides preferably are quaternary ammonium salts, which have at least one alkyl residue with 8 to 22 carbon atoms and, furthermore, low, optionally-halogenated alkyl, benzyl or hydroxyalkyl residues. The salts are preferably halides, methyl sulphates or alkyl sulphates, e.g. stearyl trimethyl ammonium chloride or benzyl bis(2-chloroethyl) ethyl ammonium bromide. 
     The tensides generally used for compositions of the invention are disclosed in publications such as: 
     &#34;McCutheon&#39;s Detergents and Emulsifiers Annual&#34;, MC Publishing Corp., Ridgewood, N.J., USA 1981; 
     H. Stache, &#34;Tensid-Taschenbuch&#34;, 2nd ed., C. Hanser, Munich, Vienna, 1981; 
     M. and J. Ash, &#34;Encyclopedia of Surfactants&#34;, vol. I-III, Chemical Publishing Co., New York, N.Y., USA 1980-1981. 
     The pesticidal compositions of the invention may comprise 0.1% to 95%, preferably 0.1% to 80% of at least one compound of formula I or Ia, 1% to 99.9% of a solid or liquid adjuvant and 0% to 25%, preferably 0.1% to 25%, of a tenside. 
     Exemplary of the compositions of the invention are: 
     Emulsion Concentrates: 
     Active ingredient: 1% to 20%, preferably 5% to 10% 
     Surface-active substance: 5% to 30%, preferably 10% to 20% 
     Liquid carrier: 50% to 94%, preferably 70% to 85% 
     Suspension-Concentrates: 
     Active ingredient: 5% to 75%, preferably 10% to 50% 
     Water: 94% to 24%, preferably 88% to 30% 
     Surface-active substance: 1% to 40%, preferably 2% to 30% 
     Wettable Powder: 
     Active ingredient: 0.5% to 90%, preferably 1% to 80% 
     Surface-active substance: 0.5% to 20%, preferably 1% to 15% 
     Solid carrier: 5% to 95%, preferably 15% to 90% 
     Dusts: 
     Active ingredient: 0.1% to 10%, preferably 0.1% to 1% 
     Solid carrier: 99.9% to 90%, preferably 99.9% to 99% 
     Granulates: 
     Active ingredient: 0.5% to 30%, preferably 3% to 15% 
     Solid carrier: 99.5% to 70%, preferably 97% to 85% 
     As commodity the inventive fungicidal compositions may preferably be in a concentrated form whereas the end-user generally employs diluted compositions. Said compositions may be diluted to a concentration of 0.001% of active ingredient (a.i.). The doses usually are in the range from 0.01 to 10 kg a.i./ha. 
     Said compositions may also comprise other auxiliaries such as stabilizers, defoamer, viscosity controlling agents, thickeners, adhesives, fertilisers or other active ingredients to obtain special effects. 
     For a more clear understanding of the invention, the following specific examples are set forth below. These examples are merely illustrations and are not to be understood as limiting the scope and underlying principles of the invention in any way. Indeed, various modifications of the invention in addition to those shown and described herein will become apparent to those skilled in the art from the following examples and foregoing description. Such modifications are also intended to fall within the scope of the appended claims. The terms HNMR, CIMS and IR as used in the examples hereinbelow designate proton nuclear magnetic resonance, mass spectrum and infrared, respectively. 
     EXAMPLE 1 
     2,6-Dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone (Compound 1) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =CH 3 , R 5  =OCH 3 , X=O, Y=O, m=1, n=0) 
     A mixture of 4-methyl-veratrol (76.1 g; 500 mmol), 2,6-dichlorobenzoyl chloride (120.4 g; 575 mmol) and iron(III)chloride (0.5 g) is heated with stirring. The reaction starts at 90° C. under formation of hydrogen chloride, the main reaction is complete within 10 min at 95° C. Subsequently, the reaction mixture is stirred for another 30 min at 100° C. and then cooled to 65° C. Upon addition of methanol (350 ml) Compound 1 begins to crystallize. A water/methanol mixture (1:1 v/v; 300 ml) is then slowly added at 40° C. and the mixture is cooled to room temperature with stirring for 30 min. The solid material is collected by vacuum filtration, three times washed with methanol/water (3:1 v/v; 100 ml each) and dried yielding colorless crystals, 148.6 g, (91.4% y) mp 101.5° C. 
     EXAMPLE 2 
     Derivatization of benzophenones 
     A) 2,6-Dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-nitro-benzophenone (Compound 2) 
     R 1  =Cl, R 2  =6-Cl, R 3  =NO 2 , R 4  =CH 3 , R 5  =OCH 3 , X=O, Y=O, m=1 n=0) 
     A portion of 2,6-dichloro-3&#39;,4&#39;-dimethoxybenzophenone (6.22 g, 20 mmol), prepared analogously to Example 1, is added within 15 min into nitric acid (65%; 40 ml) which is heated to 40° C. The clear solution is stirred for 10 min at 40° C., then 1 h at room temperature. The reaction mixture is then poured into water whereupon a slowly solidifying oil forms. This material is dissolved in a small amount of N,N-dimethyl formamide under warming, then methanol is added and the mixture is chilled and filtered giving Compound 2 as yellow crystals, 5.57 g, (78% y) with mp 143° C. 
     B) 2&#39;-Amino-2,6-dichloro-4&#39;,5&#39;-dimethoxybenzophenone (Compound 3) 
     R 1  =Cl , R 2  =6-Cl, R 3  =NH 2 , R 4  =CH 3 , R 5  =OCH 3 , X=O, Y=O, m=1, n=0) 
     A portion of 2,6-dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-nitrobenzophenone (Compound 2; 3.56 g, 10 mmol) is added to a mixture of water (50 ml), glacial acetic acid (1 ml) and powdered iron (3.30 g, 60 mmol) within 15 min at 70° C. The reaction mixture is stirred at 95° C. for another 3 h. After cooling, toluene (50 ml) is added and the solid material removed by vacuum filtration. The filter cake is washed with toluene. The filtrate and washings are combined and washed with water, dried and then applied onto a flash chromatography column (silica gel, 50 g). The column is consecutively eluted with toluene, and toluene containing 1%, 2%, 5% and 10% of acetone (250 ml each). The fraction eluted by 10% acetone is concentrated in vacuo to a final volume of 10 ml whereby Compound 3 crystallizes yielding yellow crystals, 1.61 g, (49% y) mp 181° C. 
     C) 2,6-Dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-formylamino-benzophenone (Compound 4) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =NHCHO, R 4  =CH 3 , R 5  =OCH 3 , X=O, Y=O, m=1, n=0) 
     A mixture of 2&#39;-amino-2,6-dichloro-4&#39;,5&#39;-dimethoxybenzophenone (Compound 3; 0.82 g, 2.5 mmol) and formic acid (30 ml) is heated at reflux temperature for 24 h, and evaporated in vacuo. The residue is dissolved in a small amount of toluene, Compound 4 crystallizes upon addition of cyclohexane giving colorless crystals, 0.64 g, (72% y) with mp 152° C. 
     D) 2,6-Dichloro-5&#39;-hydroxy-4&#39;-methoxy-2&#39;-methylbenzophenone (Compound 5) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =CH 3 , R 5  =OH, X=O, Y=O, m=1, n=0) 
     A mixture of 2,6-dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone (Compound 1; 2.5 g, 7.7 mmol), hydrogen bromide/acetic acid (33%, 10 ml) and glacial acetic acid (10 ml) is stirred for 1.5 h at 75° C., poured into water (100 ml) and twice extracted with dichloromethane (50 ml each). The extracts are combined, dried, and concentrated in vacuo. The resulting oil is applied onto the top of a flash chromatography column (silica gel, 30 g). Elution is carried out with toluene and toluene/acetone, 9:1 (500 ml each). The fractions containing the material with an R f  =0.54 (silica gel; toluene/acetone, 9:1) are combined and the solvent is evaporated in vacuo until a final volume of 20 ml is reached. The solution is then extracted three times with aqueous sodium hydroxide (2N; 30 ml each). The aqueous layer is acidified with hydrochloric acid (6M) and the precipitate is collected by vacuum filtration and dried to give Compound 5 as colorless crystals, 1.1 g, (45.9% y) mp 152° C. 
     E) 2,6-Dichloro-4&#39;-methoxy-2&#39;-methyl-5&#39;-n-propoxy-benzo-phenone (Compound 6) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =CH 3 , R 5  =O-n-C 3  H 7 , X=O, Y=O, m=1, n=0) 
     A mixture of 2,6-dichloro-5&#39;-hydroxy-4&#39;-methoxy-2&#39;-methylbenzophenone (Compound 5; 1.0 g, 3.2 mmol), n-propyl bromide (0.5 g, 4 mmol), potassium carbonate (2.8 g, 20 mmol) and ethanol (10 ml) is stirred for 6 h at 80° C., filtered and the filtrate is evaporated in vacuo. The residue is applied onto a flash chromatography column (silica gel, 30 g). Elution with toluene (750 ml) yields Compound 6 as a brown oil, 800 mg, (70.7% y) which slowly crystallizes (mp 73°-75° C.). 
     F) 2,6-Dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methyl-benzophenthione (Compound 7) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =O--CH 3 , R 5  =O--CH 3 , X=S, Y=O, m=1, n=0) 
     A mixture of 2,6-dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone (Compound 1; 3.25 g, 10.0 mmol), phosphorus pentasulphide (2.22 g, 10.0 mmol) and toluene (50 ml) is stirred at 110° C. for 5 h, treated with p-dioxane, stirred at 100° C. for a further 24 h. The supernatant is decanted from black, tarry reaction products, silica gel (15 g) is added and the solvent is evaporated in vacuo. A flash chromatography column is packed with silica gel (100 g) and the charged silica gel is layered on top of it. The column is subsequently eluted with petrol ether/acetone (500 ml, 98:2, v/v) and petrol ether/acetone (750 ml, 95:5, v/v) yielding Compound 7 as a dark green oil 40 mg, (1.2% y), which slowly solidifies. When the oil is triturated with cyclohexane three times, it gives a solid, mp 142° C. 
     EXAMPLE 3 
     Using essentially the same procedures described hereinabove for Examples 1 and 2 and employing standard derivatization techniques where appropriate, the following compounds are prepared and shown in Table I. 
     
         TABLE I  -  ##STR10##                                                                     C omp.  No. R.sup.1 R.sup.2 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 Y Mp °C.   8 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 H O  87                   9 Cl 6-Cl H CH.sub.3 C.sub.2 H.sub.5 OCH.sub.3 H O 106  10 Cl 6-Cl H CH.sub.3 CH.sub.3 Cl H O 168  11 Cl 6-Cl 3-NO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  12 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 H O 69-71  13 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(O)C.sub.2 H.sub.5 H O 142-145      14 Cl 6-Cl H CH.sub.3 CH.sub.3 H H O  89                         15 I H H CH.sub.3 CH.sub.3 OCH.sub.3 H O 66-68   16 Cl 6-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 H O  56                   17 Cl 6-CH.sub.3 H F CH.sub.3 OCH.sub.3 H O  95  18 (CHCH).sub.2 6-Cl CH.sub.3 CH.sub.3 OCH.sub.3 H O 19 I 3-I 5-I CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  20 Br 5-Br H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  21 Cl 4-NO.sub.2 H CH.sub.3 CH.sub.3 OCH.sub.3 H O 126-128  22 Cl 6-Cl H CH.sub.3 CH.sub.3 SCH.sub.3 H S 105  23 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2-OCH.sub.3 O  92                24 Cl 6-Cl H CH.sub.3  CH.sub.2  O H O 142  25 Cl 6-Cl H CH.sub.3 CH.sub.3 I H S              26 Br 5-OCH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 I O oil  27 Cl 5-Br H CH.sub.3 CH.sub.3 OCH.sub.3 I O 94-96  28 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(O)CH(CH.sub.3).sub.2 I O 132-135   29 Cl 5-Cl 6-OCH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 I O oil  30 Cl 6-Cl H CF.sub.3 CH.sub.3 Cl I O                             31 Cl 6-Cl H CH.sub.3 CH.sub.3 OCHF.sub.2 I O 126-128   32 CF.sub.3 5-CF.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 I O  98-101  33 Cl 6-Cl H CH.sub.3 CH.sub.3 H 3-OCH.sub.3 O 100-125             34 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(O)C(CH.sub.3).sub.3 H O 167  35 Cl 6-Cl H CH.sub.3 H OH H O 201-203  36 Cl 6-Cl H SCH.sub.3 CH.sub.3 OCH.sub.3 H O 185  37 Cl 6-Cl H S(O.sub.2)CH.sub.3 CH.sub.3 OCH.sub.3 H O 163  38 Cl 6-Cl H CH.sub.3 CH.sub.3 CH.sub.3 3-CH.sub.3 O  78                  39 Cl 6-Cl H S(O)CH.sub.3 CH.sub.3 OCH.sub.3 H O 178   40 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2  CHCH.sub.2 H O oil              41 Cl 3-Cl 5-Cl CH.sub.3 CH.sub.3 OCH.sub.3 H O  99-101                                                      42 Cl 6-Cl H CH.sub.3 CH.sub.3 (CH.sub.2).sub.2  O H O oil                             43 Cl 6-Cl H CH.sub.3 CHF.sub.2 OCHF.sub.2 H O 65-68   44 CF.sub.3 6-CF.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 H O 105-107  45 Cl 6-Cl H CHCH.sub.2 CH.sub.3 OCH.sub.3 H O                     46 I 6-F H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil   47 Cl 3-Cl H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 H O  97                  48 Cl 6-Cl H CH.sub.3 C.sub.2 H.sub.5 OC.sub.2 H.sub.5 H O  77                                                            49 Cl 6-Cl H CHCHCN CH.sub.3 OCH.sub.3 H O   50 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 3-Br O  86                      51 Cl 4-Cl 5-Cl CH.sub.3 CH.sub.3 OCH.sub.3 H O 160   52 Cl 6-Cl H CH.sub.3 CH.sub.3 C.sub.4 H.sub.9  -t H O 124                53 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.4 H.sub.9 -n H O  51                                                         54 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.4 H.sub.9  -i H O oil                              55 Cl 6-Cl H CH.sub.3 CH.sub.3 H H S   56 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5 H O 119-12157 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.5 H.sub.11 -n H O 46-48     58 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.3 H.sub.7 -i H O oil  59 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2-OH O 161                 60 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 C(O)OC.sub.2 H.sub.5 H O 105-108  61 Cl 6-Cl H CH.sub.3 CH.sub.3 H 2-OCH.sub.3 O 135 62 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2-OC.sub.2 H.sub.5 O  72  63 Cl 6-Cl H CH.sub.3 CH.sub.3 Cl H S                             64 Cl 4-Cl 6-Cl CH.sub.3 CH.sub.3 OCH.sub.3 H O 108-109  65 Cl 6-Cl H CH.sub.3 CH.sub.3 Br H S  66 F 6-F H CH.sub.3 CH.sub.3 OCH.sub.3 H O 75-77  67 Cl H H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  68 Cl 4-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  69 Cl 6-Cl H CH.sub.3 CH.sub.3 CH.sub.3 H O 135-138  70 Cl 6-Cl H CF.sub.3 CH.sub.3 Br H O  71 Cl 5-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 H O 100-102  72 Cl 6-Cl H C.sub.2  H.sub.5 CH.sub.3 OCH.sub.3 H O oil                   73 Cl 3-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  74 Cl 6-Cl H CN CH.sub.3 OCH.sub.3 H O 120  75 F 6-CF.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil   76 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2  CN H O 127                      77 Cl 6-F H CH.sub.3 CH.sub.3 OCH.sub.3 H O 72-73  78 Cl 6-Cl H I CH.sub.3 OCH.sub.3 H O 101  79 Cl 6-Cl H C.sub.3 H.sub.7 -n CH.sub.3 OCH.sub.3 H O  72                80 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(O)CH.sub.3 H O 156-159  81 Cl 6-Cl H Br CH.sub.3 OCH.sub.3 H O 124  82 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 CCH H O  87                      83 Cl 6-Cl H H CH.sub.3 H 3-OCH.sub.3 O 127  84 Cl 6-Cl H CH.sub.3 H H 3,6-di-CH.sub.3 O 122                      85 Cl 6-Cl H CH.sub.3 CH.sub.3 H 3,6-di-CH.sub.3 O 111   86 Cl 6-Cl H CF.sub.3 C(O)-2,6-Cl.sub.2 C.sub.6 H.sub.3 H H O 186   87 CH.sub.3 6-CH.sub.3 H H CH.sub.3 H 3-OCH.sub.3 O  84  88 Cl 6-Cl H H CH.sub.3 H 3-Br O 129                       89 Cl 6-Cl H H CH.sub.3 Br 3-OCH.sub.3 O 140  90 Cl 6-Cl H OCH.sub.3 CH.sub.3 OCH.sub.3 H O 124  91 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(O)H H O 156   92 OCH.sub.3 6-OCH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 H O 113  93 Cl 6-Cl H COOH CH.sub.3 OCH.sub.3 H O 174                     94 Cl 6-Cl H CH.sub.3 CH.sub.3 S(O).sub.2  CH.sub.3 H SO.sub.2 233                95 Cl 6-Cl H CH.sub.3 CH.sub.3 SOCH.sub.3 H SO 227   96 Cl 6-Cl H CH.sub.3 CH.sub.3 O.sub.n -C.sub.7 H.sub.15 H O oil    97 Cl 6-Cl H CH.sub.3 CH.sub.3 O.sub.n -C.sub.8 H.sub.17 H O oil   98 Cl 6-Cl H CH.sub.3 CH.sub.3 O.sub.n -C.sub.10 H.sub.21 H O oil   99 CH.sub.3 4-CH.sub.3 6-CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 H O  74  100 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 -c-C.sub.3 H.sub.5 H O oil101 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 -c-C.sub.6 H.sub.11 H O 108  102 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub.2CH(CH.sub.3).sub.2 H O oil  103 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 CHC(CH.sub.3).sub.2 H O oil    104 CH.sub.3 6-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 H O 90-92   105 Cl 6-Cl H CH.sub.3 CH.sub.3 Oc-C.sub.5 H.sub.9 H O oil    106 Cl 6-Cl H CH.sub.3 CH.sub.3 Oc-C.sub.6 H.sub.11 H O oil  107 Cl 6-Cl H H CH.sub.3  3!-(CHCH).sub.2 - 2! H O 155-157     108 Cl 6-Cl H CH.sub.3 CH.sub.3 ONa H O glass  109 Cl 6-Cl H CH.sub.3 CH.sub.3 OSi(CH.sub.3).sub.3 H O oil  110 Br 6-Br H CH.sub.3 CH.sub.3 OCH.sub.3 H O 102  111 Cl 6-Cl H CH.sub.3 CH.sub.3 Oh H O  98                               112 Cl 6-Cl H OCH.sub.3 CH.sub.3 Br 2-OCH.sub.3 O 183  113 CN H H CH.sub.3 CH.sub.3 OCH.sub.3 H O  76                           114 Cl 6-Cl H CH.sub.3 CH.sub.2  O 2-OCH.sub.3  98                                                        115 Cl 6-Cl H N HCH.sub.3 CH.sub.3 OCH.sub.3 H  163  116 Cl 6-Cl H OH CH.sub.3 OCH.sub.3 H O  80                              117 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2Si(CH.sub.3).sub.3 H O oil  118 Cl H H CH.sub.3 CH.sub.3 OCH.sub.3 H O 62-64  119 Cl 3-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2-OCH.sub.3 O oil  120 Cl 4-Cl 6-Cl CH.sub.3 CH.sub.3 OCH.sub.3 H O 126  121 F 6-F H CH.sub.3 CH.sub.3 OCH.sub.3 H O  84                          122 Cl 5-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  123 Cl 6-Cl H OCH.sub.3 CH.sub.3 CH.sub.3 6-OCH.sub.3 O 115  124 I H H CH.sub.3 CH.sub.3 OCH.sub.3 2-OCH.sub.3 O oil  125 Br H H CH.sub.3 CH.sub.3 OCH.sub.3 H O  34                           126 Cl 6-Cl H CH.sub.3 CH.sub.3 On-C.sub.6 H.sub.13 H O oil  127 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.3 H.sub.7 O  46 128 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.7 H.sub.15 O oil  129 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.10 H.sub.21 O oil    130 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2-OC(O)CH.sub.3 O 164   131 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.5 H.sub.11 O oil  132 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.2CH(CH.sub.3) .sub.2 O 101  133 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2OCH.sub.2CHCH.sub.2 O  73134 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2OCH.sub.2 CCH O 123   135 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2Oc-C.sub.5 H.sub.9 O 89  136 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 6OCH.sub.2C.sub.6 H.sub.5 O 80  137 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.12 H.sub.25 O oil    138 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2OCH.sub.2 -c-C.sub.6 H.sub.11 O  88                                                            139 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2On-C.sub.6  H.sub.13 O oil             140 Cl 6-Cl H CH.sub.3 CH.sub.3 On-C.sub.12 H.sub.25 H O oil  141 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 C(O)N(C.sub.2 H.sub.5).sub.2 H O  97 142 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2  C(O)NH.sub.2 H O 136            143 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.2OCH.sub.3 O  84                               144 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH(C.sub.2  H.sub.5).sub.2 H O oil                                        145 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub.2OH H O  87                      146 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub. 3OH H O  86                                                               147 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 -p-C.sub.6 H.sub.4CH.sub.3 H O oil148 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 -p-C.sub.6  H.sub.4C(CH.sub.3).sub.3 H O 119  149 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2OCH.sub.2 C(O)-morpholide O oil  150 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub.2 OCH.sub.3 H O oil 151 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2C(O)-morpholide H O 163152 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 -p-C.sub.6 H4OCH.sub.3 H O oil  153 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub.3 OC.sub.6 H.sub.5 H O oil  154 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.3 -morpholin yl ×  HCl O 225                                                      155 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.2N(CH.sub.3).sub.2 ×  HCl O 103                                                         156 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.2N(C.sub.2 H.sub.5).sub.2 ×  HCl O 144                                          157 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.2 H.sub.5 2-OCH.sub.3 O  68                      158 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.3 Cl O  87                                               159 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 2O(CH.sub.2).sub.3 -piperidyl × HCl O  70   160 Cl 6-Cl H CH.sub.3 n-C.sub.7 H.sub.15 OCH.sub.3 H O  51   161 Cl 6-Cl H CH.sub.3 n-C.sub.3 H.sub.7 OCH.sub.3 H O  80    162 Cl 6-Cl H CH.sub.3 n-C.sub.4 H.sub.9 OCH.sub.3 H O  89   163 Cl 6-Cl H CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 H O  96    164 CH.sub.3 3-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 6-OCH.sub.3  O  82 165 CH.sub.3 5-CH.sub.3 H CH.sub.3 CH.sub.3 OCH.sub.3 6-OCH.sub.3 O oil   166 Cl 6-Cl H Cl CH.sub.3 OCH.sub.3 H O 114  167 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2).sub.3CO.sub.2 C.sub.2 H.sub.5 H O oil  168 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 C.sub.6 H.sub.4CF.sub.3 -p H O 115-117  169 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 SiC.sub.2 H.sub.5  (CH.sub.3).sub.2 H O  85                                                 170 Cl 6-Cl H CH.sub.3 CH.sub.3 OC(CH.sub.3).sub.3 H O 102  171 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH H O oil  172 Cl 6-Cl H CH.sub.3 CH.sub.3 O(CH.sub.2)4Br H O oil  173 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 6-O(CH.sub.2).sub.3 N(C.sub.2 H.sub.5).sub.2 O oil  174 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 6-OCH(CH.sub.3).sub.2 O 108    175 Cl 6-Cl H CH.sub.3 CH.sub.3 OCH.sub.3 6-OCH.sub.2  CH.sub.2OCH.sub.2 CH.sub.2  OCH.sub.3 O oil                               176 Cl 6-Cl H CH.sub.3 CH.sub.3 OCOC.sub.6 H.sub.3 Cl.sub.2  -2,6 6-OCH.sub.3 O 186-189           177 Cl 6-Cl H H CH.sub.3 OCH.sub.3 6-OCH.sub.3 O  97                                                         178 Cl 6-Cl H CH.sub.3 CH.sub.3 CH.sub.3 6-OCH.sub.3 O 106  179 Cl 6-Cl H OCH.sub.3 CH.sub.3 OCH.sub.3 6-OCH.sub.3 O 121-123    180 Cl 6-Cl H CH.sub.3 CH.sub.3 NHCOCH.sub.3 H O 155  181 Cl 6-Cl H CH.sub.3 CH.sub.3 OH 6-OH O 182  182 CF.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 6-OCH.sub.3 O oil  183 CF.sub.3 H H CH.sub.3 CH.sub.3 OCH.sub.3 H O oil  184 Cl 6-Cl H CH.sub.3 CH.sub.3 OC.sub.4 H.sub.9 -n 6-OC.sub.4 H.sub.9 -n O oil  185 Cl 6-Cl H CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 H O 110  186 Cl 6-Cl H CH.sub.3 H NO.sub.2 H O 149 
    
     EXAMPLE 4 
     2&#39;-n-Butoxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6&#39;-methylbenzophenone (Compound 187) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =CH 3 , R 5  =OCH 3 , R 6  =2--O--(CH 2 ) 3  --CH 3 , X=O, Y=O, m=1, n=1) 
     a) 2,6-Dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-hydroxy-6&#39;-methylbenzophenone (Compound 59) 
     Aluminum chloride (14.67 g, 0.1 mol), 2,6-dichlorobenzoyl chloride (20.95 g, 0.1 mol) and a solution of 3,4,5-trimethoxytoluene (18.22 g, 0.1 mol) in dichloromethane (50 ml), are slowly and consecutively added to dichloromethane stirred at 0° C., stirred for 1 h at ice bath temperatures and for 16 h at room temperature, and poured into ice. The organic layer is separated, washed with dilute hydrochloric acid and water, dried, and, after addition of silica gel (100 g), concentrated in vacuo. A flash chromatography column is packed with silica gel (400 g) and the charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1l) yields 2,6-dichloro-3&#39;4&#39;-dimethoxy-2&#39;-hydroxy-6&#39;-methylbenzophenone, 10.35 g, (30% y). 
     b) 2,6-Dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-hydroxy-6&#39;-methylbenzophenone, potassium salt (Compound 188) 
     (R 1  =Cl, R 2  =6-Cl, R 3  =CH 3 , R 4  =CH 3 , R 5  =OCH 3 , R 6  =2-OK, X=O, Y=O, m=1, n=1) 
     A solution of 2,6-dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-hydroxy-6&#39;-methyl-benzophenone (10.24 g, 30 mmol) is dissolved in ethanolic potassium hydroxide (1.98 g, 30 mmol; 85% in ethanol (100 ml)) and stirred at 70° C. for 15 min. The solvent is then evaporated in vacuo. The residue is dissolved in hot ethanol (50 ml), toluene is added and the solvent is evaporated in vacuo giving Compound 188, 11.7 g. 
     c) 2&#39;-n-Butoxy-2,6-dichloro-3&#39;,4&#39;-dimethoxy-6,-methylbenzophenone (Compound 187) 
     A mixture of 2,6-dichloro-3&#39;,4&#39;-dimethoxy-2&#39;-hydroxy-6&#39;-methyl-benzophenone, potassium salt (1.13 g; 3 mmol), 1-bromobutane (0.69 g, 5 mmol) and dimethyl formamide (5 ml) are stirred at 100° C. for 8 h, and concentrated in vacuo. The residue is dissolved by shaking with a toluene/water mixture, after separation, the organic layer is collected washed with water and dried. After addition of silica gel (5 g), the solvent is evaporated. A flash chromatography column is packed with silica gel (25 g) and the charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (95/5, 500 ml) gives the title compound, 0.82 g, (69% y) as colourless crystals, mp. 70° C. 
     EXAMPLE 5 
     Using essentially the same procedures described in Examples 1, 2 and 4 hereinabove and employing, if required, standard derivativatization methods, the following compounds shown in Table II are prepared 
     
                                           TABLE II__________________________________________________________________________ ##STR11##Comp.No. R.sup.1  R.sup.2        m R.sup.3             YR.sup.4                 R.sup.5   R.sup.6                               n mp °C.__________________________________________________________________________189 CH.sub.3  2,3,5,6-CH.sub.3        4 CH.sub.3             OCH.sub.3                 OCH.sub.3 H   0 103190 CH.sub.3  CH.sub.3        5 CH.sub.3             OCH.sub.3                 OCH.sub.3 H   0   142-144.5191 CH.sub.3  2,3,5,6-CH.sub.3        4 CH.sub.3             OCH.sub.3                 OCH.sub.3 5-OCH.sub.3                               1 113192 CH.sub.3  2,3,5,6-CH.sub.3        4 CH.sub.3             OCH.sub.3                 OCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                           H   0  73193 CH.sub.3  2,3,5,6-CH.sub.3        4 CH.sub.3             OCH.sub.3                 OCH.sub.2 CH.sub.2 CH.sub.3                           H   0  85194 CH.sub.3  2,3,5,6-CH.sub.3        4 CH.sub.3             OCH.sub.3                 OCH.sub.3 5-OH                               1 137__________________________________________________________________________ 
    
     EXAMPLE 6 
     2,6-Dichloro-3&#39;,4&#39;-dimethoxybenzophenone oxime (Compound 195) 
     R 1  =Cl; R 2  =6-Cl; R 3  =H; Y=O; R 4  =CH3; R 5  =H; R 6  =4-OCH 3  ; R=H 
     A stirred dispersion of anhydrous aluminum chloride (2.93 g, 22 mmol) in methylene chloride at ice-bath temperatures is treated sequentially with a solution of 2,6-dichlorobenzonitrile oxide (3.76 g, 20 mmol) in methylene chloride and, dropwise, with a solution of veratrole (3.32 g, 24 mmol) in methylene chloride, stirred for 0.5 hour, allowed to warm to room temperature, stirred for 4-5 hours and poured into a mixture of ice and HCl. The resultant phase mixture is separated. The organic phase is washed with 2M HCl, treated with silica gel and evaporated to dryness in vacuo. The residue is placed on top of a column of silica gel and eluted with mixtures of petroleum ether and ethyl acetate (5%, 10% and 20% pet ether, respectively) to give the title product as a white solid, 1.25 g (19% y) mp 153° C. 
     EXAMPLE 7 
     2,6-Dichloro-4&#39;, 5&#39;-dimethoxy-2&#39;-methylbenzophenone O-n-propyloxime (Compound 196) 
     R 1  =Cl; R 2  =6-Cl; R 3  =CH 3  ; Y=O; R 4  =CH 3  ; R 5  OCH 3  ; R 6  =H; R=CH 2  CH 2  CH 3   
     A stirred solution of 2,6-dichloro-4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone oxime (1.5 g, 4.4 mmol) in anhydrous tetrahydrofuran is treated with a 60% dispersion of sodium hydride in mineral oil (0.2 g, 4.8 mmol NaH). After the cessation of hydrogen gas evolution, the reaction mixture is treated with n-propyliodide (0.82 g, 5.3 mmol), allowed to stand at room temperature for 12 hours, and diluted with water. The resultant phase mixture is extracted with ethyl acetate. The organic phases are combined and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and petroleum ether/ethyl acetate, 8/2, to give the title product as a yellow oil, 0.4 g (23.8% y) identified by NMR (67:23, E/Z isomer ratio). 
     EXAMPLE 8 
     2,6-Dichloro4&#39;,5&#39;-dimethoxy-2&#39;-methylbenzophenone-O-acetyl-oxime (Compound 197) 
     R 1  =Cl; R 2  =6-Cl; R 3  =CH 3  ; Y=O; R 4  =CH 3  ; R 5  =OCH 3  ; R 6  =H; R=COCH 3   
     A stirred solution of 2,6-dichloro-4&#39;,5&#39;-dimethoxy 2&#39;-methylbenzophenone oxime (2.3 g, 6.8 mmol) in anhydrous tetrahydrofuran is treated with a 60% dispersion of sodium hydride in mineral oil (0.3 g, 7.5 mmol NaH). After the cessation of hydrogen gas evolution, the reaction mixture is treated with acetylchloride (0.55 g, 7.5 mmol) at room temperature, allowed to exotherm to 30° C., stirred at ambient temperatures for 2 hours, concentrated in vacuo, treated with water, and filtered. The filtercake is washed with water, dried and recrystallized from methanol to give the title product as white crystals, 1.0 g (38.5% y), mp 158°-149° C., identified by NMR (100% E isomer). 
     EXAMPLE 9 
     Using essentially the same procedures described for Examples 6-8 hereinabove the following compounds are obtained and shown in Table III. 
     
                       TABLE III______________________________________ ##STR12##CompoundNo.      R            R3      R6    mp °C.______________________________________198      H            F       H     oil199      H            H       H     153200      H            CH.sub.3                         H     60-70201      H            CH.sub.3                         6-OCH.sub.3                               219-220202      CH.sub.3     CH.sub.3                         H     112-115203      CH(CH.sub.3).sub.2                 CH.sub.3                         H     117204      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                 CH.sub.3                         H     oil______________________________________ 
    
     EXAMPLE 10 
     
         ______________________________________Formulation: Emulsion Concentrate______________________________________active compound    200 g/lethoxylated castor oil              100 g/ltetrahydrofurfuryl alcohol              793 g/l______________________________________ 
    
     EXAMPLE 11 
     The fungicidal activity of the compositions and compounds of the invention is investigated by means of the following tests. 
     a) Activity Against Cereal Powdery Mildew (Erysiphe graminis f.sp. hordei and f.sp. tritici) 
     This test measures the prophylactic activity of test compositions and test compounds applied as a foliar spray. Cereal seedlings (barley, cv Golden Promise; wheat, cv Kanzler) are grown to the 1 leaf stage. The plants are then sprayed with a solution of test compound in water, made up from a 5,000 ppm stock solution in acetone containing 5,000 ppm of TRITON®X 155 (a non-ionic polyoxyethylene ether surfactant). Plants are treated using an automated spray line with atomizing nozzles. The spray volume is 20 ml. One to three days after treatment, the seedlings are inoculated with powdery mildew by shaking stock culture plants with sporulating pathogen (barley--Erysiphe graminis f.sp. hordei; wheat--Erysiphe graminis f.sp. tritici) over them. Thereafter, the plants are kept for 3h without air movement in order to allow the spores to settle on the leaves. The plants are then kept in the greenhouse until symptoms occur. Assessment is based on the percentage of diseased leaf area compared with that on control leaves. 
     b) Activity Against Apple Powdery Mildew (Podosphaera leucotricha) 
     This test measures the prophylactic activity of test compositions and test compounds, applied as a foliar spray. Apple seedlings (cv Morgenduft) are grown to the 6-7 leaf stage and then cut back to 3 leaves, taking off the oldest and youngest leaves. The plants are sprayed with a solution (20 ml) of test compound in water, made up from a 5,000 ppm stock solution in acetone containing 5,000 ppm of TRITON®X 155. The plants are treated using an automated spray line with atomizing nozzles. One to three days after treatment, the seedlings are inoculated with powdery mildew by shaking stock culture plants with sporulating pathogen over them. Thereafter, the plants are kept for 3 h without air movement. The plants are then kept in the greenhouse until symptoms occur. Assessment is based on the percentage of diseased leaf area of treated plants compared with that of control plants. 
     c) Activity Against Grapevine Powdery Mildew (Uncinula necator) 
     This test measures the direct protectant activity of test compositions and test compounds applied as foliar spray. Cuttings of grapevine (cv Muller-Thurgau) are grown to the 6-8 leaf stage and then cut back to 4 equally sized leaves. The plants are sprayed to run-off in a spray cabinet with a solution (20 ml) of test compound in water made up from a 5,000 ppm stock solution in acetone containing 5,000 ppm of TRITON®X 155. Two days after treatment, the cuttings are inoculated with conidia of Uncinula necator in a special spore setting tower. The spores are blown from freshly sporulating grape leaves (U. necator stock culture) into the upper hole of the settling tower and are allowed to settle on the leaves for 5 min. Then the plants are kept in a phytotron at 18° C. night and 22° C. day temperature at an interval of 12 h night and 12 h day. Illumination is accomplished by fluorescent tubes at 11,200 lux. Assessment is carried out after 21 days by visual inspection and based on the percentage of the diseased leaf area of the three youngest leaves compared with that on control plants. The results of the tests are set out in Table IV below, in which the compounds are identified by reference to the preceding Compound Nos. allocated in Examples 1 to 9 above. Absence of a rating indicates that none of the tests described above was carried out. A rating 0 indicates disease as untreated control, a rating 100 indicates no disease. 
     
                       TABLE IV______________________________________Erysiphe graminis   Podosphaera                          Uncinula   barley    wheat     leucotricha                                necatorComp. No.   100 ppm   100 ppm   100 ppm  200 ppm______________________________________*1      100       100       96       84*2      99        100       0        41*3      0         6         04       95        100       415       94        99        416       99        100*8      100       100       100      95*9      0         70        95*10     85        100       44       88*11     0         0         0*12     23        0         013      87        100*14     0         36        0*15     99        73        016      100       9417      25        5         7718      89        57        7319      19        26        1520      100       100       2821      9         19        1523      100       100       10024      94        100       5326      82        79        3327      90        100       8928      100       9829      99        93        9731      99        10032      1         28        833      39        9834      0         035      0         22        936      49        6137      70        3738      42        7739      28        8540      100       10041      49        9943      23        4944      89        38        1046      100       10047      95        10048      84        90        10050      4         6         9451      51        2552      0         053      100       100*54     100       10056      100       100       11*57     99        100*58     100       100*59     0         160      0         3262      100       100*64     95        99        71       63*66     0         0         0*67     43        0         0*68     0         0         0*69     0         28        0*71     99        32        10*72     55        72        0*73     99        94        26       33*74     0         0         16*75     61        34        076      33        57*77     41        99        90*78     0         85        0*79     0         0         080      76        10082      100       10084      0         085      33        2886      0         1791      93        100*93     0         17*94     0         0*95     91        0*96     100       100       100*97     100       100       100*98     100       100       100*99     86        6         29*100    100       100       100*101    100       100       87*102    100       100       100*103    100       100       10*104    100       14        27*105    100       100       100*106    100       100*107    0         21*108    100       100*109    100       100*110    100       100*111    95        100*112    0         19*113    0         28*114    0         17*115    100       60*116    100       64*117    100       100       6*118    99        13        66*119    100       89        98*120    100       89        46*121    100       100       37*122    100       100       28*123    0         44        9*124    100       100       89*125    100       28        8*126    100       100       100*127    100       100       100*128    100       100       100*129    100       100       100*130    0         78        0*131    100       100       100*132    100       100       100*133    100       100       100*134    100       100       100*135    100       100       100*136    100       100       100*137    100       100       97*138    100       100       100*139    100       100       100*140    100       100       100*141    97        100       0*142    97        100       53*143    100       100       100*144    100       100       100*145    84        97        80*146    65        91*147    100       100*148    100       100*149    39        66*161    48        77        100*162    23        4         100*163    97        90        7166     100       100       --167     100       97        20168     100       100       2169     100       100       0170     100       100       100171     97        100       0172     100       97        100173     26        53        0174     100       100       98175     100       100       100176     0         0         8177     52        0         0178     100       100       100180     95        19        --181     5         0         6182     100       93        0183     100       74        0184     100       100       100185     0         0         0186     0         100       100189     100       100       100190     98        8         68191     100       100       99196     0         82        87197     71        78        1199     0         0         --200     100       100       41201     98        0         --202     0         92        92______________________________________ *indicates the infection with Erysiphe graminis and Podosphaera leucotricha was carried out 72 h after treatment