IT8109326A1 - DERIVATIVES OF BENZOXZOLONE, PROCEDURES FOR THE PREPARATION OF THESE AND COMPOSITIONS CONTAINING THEM - Google Patents

Description

DOCUMENTATION

BOUND

? DERIVATIVES OF BENZOXZOLONE. PROCEDURES FOR THE PREPARATION OF THESE AND COMPOSITIONS THAT CON-HOLD THEM "

SUMMARY

Certain new benzoxazolone derivatives containing either the 5,6,7-trlchlorine group or at least one lower alkyl group and at least one halogen atom, are highly active against a large variety. of plant diseases from bacteria and fungi and have a ph itotoxicity? reduced. These derivatives are also useful for controlling the growth of numerous fungi and bacteria capable of deteriorating industrial materials.

DESCRIPTION

This invention relates to new benzoxazolone derivatives, the processes for the preparation of these, the fungicidal and bactericidal compositions containing the derivatives and the methods for combating numerous fungi and bacteria using the derivatives and compositions

It is well known in the art that certain benzoxazolone derivatives are useful as fungicides and batteries in agriculture and horticulture. For example, the German patent No. 1023627 describes the properties antifungal and antibacterial of some derivatives of benzoxazolone, the benzene ring of which carries a substituent such as the 5-chloro, 5,6- or 5,7-chlorine group or the 4,5,7-trichloro group but no substitutes alkyl. The German patent ?? 1147007 describes the properties antimicrobials of 4,5,6,7-tetrachlor benzoxazolone, while the U.S.S.R.

Ne 355008 describes these properties? of 4,5,6-trichloro benzoxazolone?

Furthermore, the Japanese patent N? 23519/65 describes the properties fungicidal and bactericidal of the derivatives of benzoxazolone having the formula:

R3 CO - R4

where R-j = ?? R-, * Cii, Rg = R3 = Hj R ^ = et, R1 = R3 = H; R1 and R2 = C? T R3 = H; or R ^ = R ^ = = C ?; And ? phenyl optionally replaced by halogen, nitro, lower alkyl or lower alkoxy.

Yup ? synthesized and carefully studied a variety? of further new derivatives of benzoxazole in order to develop new microbicides of benzoxazolone that possess a low toxicity? and good security and have a? high activity? against a wide range of Fungi and bacteria. As a result yes? now discovered new derivatives of benzoxazolone which have not been described in the literature and which are very useful as fungicides and bactericides. The derivatives of this invention carry in the benzene ring or at least one lower alkyl and at least one halogen substituent, or substituent 5,6,7-trichloro. Have these new derivatives of the invention shown to possess? re ownership considerably greater fungicide and bactericide than those of the known 4,5,7-trichlorobenzoxazolone and 4,5,6-tricolorobenzoxazolone, as will be seen? clearly from the examples given more? next An object of this invention? providing novel benzoxazolone derivatives useful as antifungal and antibacterial agents for non-medical use. Another object of the invention? provide processes for the preparation of these benzoxazo ion derivatives.

A further object of this invention? providing fungicidal or bactericidal compositions for non-medical uses containing the derivatives as an active ingredient. Still a further object of the invention? provide a method of fighting fungi and bacteria using de rivatls or compositions containing them.

Other objects and advantages of this invention will be highlighted by the following description.

According to the present invention, a benzoxazolone compound having general formula is provided:

C = 0 (I)

wherein X represents a lower alkyl group; Y represents a halogen atom; m? 0 or an integer number from 1 to 3, n? an integer from 1 to 3 and the sum of m n? an integer from 2 to 4 * provided? when m? 0, n? 3 and YR stands for the 5,6,7-trichloro group; and R represents a hydrogen atom or an alkyl, alkylcarbonyl, haloalkylcarbonyl, alkyloxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, mono- or di-alkylamino carbonyl, alkylsulfonyl, phenylsulfonyl group or an optionally substituted phenylaraminocarbonyl or benzoyl group.

In the general formula (I), X? a lower alkyl group containing from 1 to 4 carbon atoms such as the methyl, ethyl, n-propyl, isopropyl or butyl group, including the methyl group? preferable, and Y? a halogen atom such as bromine or preferably there? ro. R pu? be: an alkyl group, particularly of 1-4 carbon atoms; an alkylcarbonyl group, particularly (C1) alkylcarbonyl; a haloalkylcarbonyl group, particularly the chlorine (C1) alkylcarbonyl group; an alkyloxycarbonyl group, particularly the (C4) alkyloxycarbonyl group; an alkenylcarbonyl group, particularly the (C2 ^) alkenylcarbonyl group, an alkenyloxycarbonyl group, particularly the (C24) alkenylacarbonyl group; a mono- or di-alkylaminocarbonyl group, particularly mono- or di- (C1 alkylamine carbonyl; an alkylsulfonyl group, particularly the (C1) alkylsulfonyl group; or the phenylsulfonyl group? R may also be an optionally substituted benzoyl group, comprising the unsubstituted benzoyl group and the substituted benzoyl group such as methylbenzoyl and chlorobenzoyl; as well as an optionally substituted phenylaminocarbonyl group comprising an unsubstituted phenylaminocarbonyl group and a substituted phenylaminocarbonyl group, such as the mono- or di-chlorophenylaminocarbonyl group.

A preferred group of compounds includes those of formula (I) in which m? 0 and Y? the 5,6,7-trichloro group. Another preferential group of compounds i. that of formula (I) in which Xm? methyl, especially 7-methyl and Yn? dichloro, especially the 5 * 6-dichloro group?

Specific examples of the compounds of this invention

are shown in the following table.

TABLE i

Compound N? Structural formula Melting point (? C)

There

There

1 or \. 253 - 254 / c = o

There

2

Ci or c = o 135 - 139

CH

There

171 ~ 172 Ci o

COCH

There

4 or c = or 161 - 162

There

COC2H5

There

111 - 112 O = 0

COC ^ Hgn

There

o c = o 187 ~ 188

COCH ^ Ci

= 0 188 - 190

CO

198 - 200 C = 0

co

o c = o 157 - 159

/

G0- <O

CH

There

o = 0 163 164

C00GH

There

O c = o 173 ~ 175 w

CONHCH,

There

There

0

Or 127 - 129 C? N>?

CON (CH3) 2

There

o c = o 164 ~ 165

N /

CONH- ^ Q ^)

There

There

ci i o) = 0 235 ~ 237

No.

? <0N> H- (O,

Gl

Gl

218 - 219

Gl or 0

N> 0

'

S02GH5

Gl

C l

0

O c = o 197 - 198

I know.

Gl

Gl

or 99 - 100

Gl w> = o

COOG2H5

Gl

O c = o 104 ~ 105 w

GOOC ^ H ^ -n

Gl

Gl

? 0.

\

OR 129 - 150

Gl w / = 0

COOC ^ H ^ -iso

There

o = 0 182 ~ 184

CH3

There

0 \

O c = o 150 - 159

N <7>

CH. THE

COCH ^

There

O I y \ C = 0 140 - 141

CH

C <Q> - / 0

O c = o 115 ~ 117

? 00CoHc25

--0

or 254 ~ 257

/>?

O c = o 232 ~ 234

/

o c = o 93 - 94

COCH

or \ 126 - 130

G = 0

/

C? H

2 5

There

101 ~ 103 c = o

C2H ^ O \ s ^ r l /

THE

COCH

5

There

O?) 0 106 *? 110

Ir = 0

G2H5? 0CH2Ci

There 0

O \ 115 ~ 116

= 0

CpH, l

d 5 C00CH,

There .

o c = o 251 - 252

CH,

Ci I

? or? \ 122 - 123

C = 0

/

There

o c = o 168 - 169

There

COCH

o c = o 54 ~ 56

COC ^ Hg-n

the

Or i \ 165 ~ 166

/: <M>

O c = o 213 - 215 co

CH,

IsO c = o 135 - 138

COOCH,

o c = o 170 - 172

ONHCH

o / c = o 179 ~ 180

CH

WITH

There

150 - 152

Ci or c = o

N /

? ONHY Q)

CH

or 221 - 222 c = o

w There

There

<C0NH> - (O

There

or \

C = 0 199 - 200 Ci /

SO2CH5

CH,

there

or \ 191 - 193

N /

THE

SO,

There Ko)

o c = o 248 - 250 w

O \ c = o 155 - 155 /

COCH

the

o c = o 149 ~ 151

N '

COOCH

There

O -0 218 - 219

/>

o c = o 156 ~ 158

IL3. C <W> H <X1> 5

There

^ 0

\ c = o 105 - 105

N /

I ?

CH5 <C>? C <H> 3

127 ~ 130

02 V or "iT; <c> =?

GH ^ COOCH ^

There

There 0

OR 216 - 217

C = 0

/

? -?, ?? No.

the

5 t H

O \ c = o 155 "135

/

i-C, 5H7 COGH

There

O c = o 150 - 152

N /

i-C? 5H7 COOCH

O c = o 262 - 264

CH,

Br

0

O \ c = o 173 ~ 175 Ci Nr / '

THE

COCH,

Or 0 = 0, 224 - 225

N '

o c = o 158 - 159

/

COCH

CH

o c = o 236 - 239

No.

There h

the

O c = o 134 - 136

/

? COCH

O c = o 254 ~ 256

/

CH

C?

C?

C?

o c = o. 155 - 157 H_ ^ '?'

3 Q? ?

<0> and> COCH,

C?

0

\ c = o 174 - 176

/

C? COOCH,

o c = o 275 - 277? w

o c = o 125 - 127

/

CH3 C0CH3

O c = o 288 - 289 /

There

Br 9 *

142 - 144

?? ^ COCHj

O c = o 271 - 272

/

There

O [<N> c = 0 117 - 118 ci

CH3 COCH3

i c?

_?

o c = o 161 ~ 163

<]> /

COCH =? H.

There

the

0

C = 0 96 - 98

i or N

COOCH2CH = CH2

The compounds of this invention can be prepared by means of the reaction procedures indicated in schemes A, B and C reported below and some of the compounds can be made by the method indicated in scheme D.

? . Xm. ^ Xm

Diagram A v ^ OH A 1

? or

\ B

NhR * 0> -Yn Yri

R.

(II) (III). (I) In general the formulas (1) and (II), the symbols R, X, Y, m and n have the same meanings given up to here? Compounds of formula (II) in which R?, For example, the acetyl group can be prepared with high yield by acetylating the appropriate optionally lower alkyl-substituted orthoaminophenol in a conventional manner and then halogenating the acetylation product with a required equivalent. of a halogen? The compound thus obtained can? be hydrolyzed, for example, with diluted hydrochloric acid to give the corresponding compound having form (II), wherein R? a hydrogen atom? The latter compound can? be alkylated or acylated by any conventional method to give a variety? of compounds (II)?

In general formula (III), the symbols A and B / which may be the same or different ^ each represent a halogen, alkoxy, haloalkoxy, alkylthio or amino group. Compounds of formula (II) comprise phosgenic compounds such as phosgene and diphosgene (i.e. trichloromethyl chloroformate), haloformates, halo thiolformates, carbonic diesters and urea.

According to scheme A, it is generally believed that compound (I) can be produced in two steps in which compound HA or HB? eliminated by the reaction between compound (II) and compound (III) to form an intermediate compound which? further reacted with compound (III) to allow further elimination of compound HB or HA, respectively. Thus, if a stable intermediate is formed depending on the nature of compound (III) used, it can be formed. be isolated during the process and then cyclized to produce the final compound (I). This stable intermediate can? be formed in an alternative process without resorting to the reaction between compound (II) and compound (II) and then cyclized to give compound (I).

The reaction between compounds (II) and (III) can? be carried out in the absence of any solvent but preferably in the presence of an organic solvent which p * u? also be an excess of the compound (IH) ste so. Examples of solvents to be used include hydrocarbons, halogenated hydrocarbons, ethers, esters, amyl acids, alcohols and dimethyl sulfoxide, among which the solvent suitable for use will be? selected depending on the nature of the compound (III). Pu? An acid binding agent may be used to slightly anticipate the reaction, as some of the compounds (III) can lead to the formation of an acid during the course of the reaction. The agent of bonding? acid to be used for this purpose includes organic amine ^ such as triethyl amine and pyridine ^ and inorganic bases / such as carbonate d? potassium. The reaction can? be performed at room temperature, although it can be completed in a short period of time when conducted at a high temperature.

After completion of the reaction, the subject compound of formula (i) can? be isolated and purified by any conventional method. For example, a salt or sal? of the agent d? acid bond precipitated in the reaction mixture can be filtered off when? used a binder, and then the solvent can? be evaporated from the filtrate to leave compound (s). Alternatively, it can? to be added to the reaction mixture water and / or a suitable organic solvent such as benzene, chloroform, ether and tetraldrofuran, to fractionally precipitate the subject compound therefrom?

The details of the method according to scheme A are given more? forward in examples 1-4, 11-14 and 23? Scheme B

??

\

> C? 04- Hal? Senating_ v

/ 'agent' C = 0 /

(IV)? CV) (I)

neila. general formula (IV), R, X and m are defined as above, E? a halogen atom and p? 0, 1 or 2. Can the compounds of formula (IV) be made according to the method as mentioned above for scheme A? Examples of halogenating agents (V) to be used include halogens such as chlorine and bromine and sulfuryl chloride alone and combinations of a hydrohalogenic acid and an oxidizing agent such as bleaching powder, potassium chlorate or manganese dioxide.

According to scheme B, the halogenation reaction? usually carried out in a solvent and at a high temperature to accelerate the reaction if the halogenation is carried out with a halogen such as chlorine or bromine or with sulfuryl chloride. The solven you who can? being used in that case includes water * acetic acid and halogenated hydrocarbons. If 1 * halogen-ation? conducted using a combination of an acid such as hydrochloric or hydrobromic acid and an oxidizing agent such as bleaching powder, potassium chlorate or manganese dioxide, then compound (IV) can be dissolved in the acid with subsequent addition of the powder of the oxidizing agent or a concentrated aqueous solution of this? Pu? be used, if necessary, a solvent such as 1 * acetic acid? The presence of a catalyst, for example iron, iron chloride, phosphorous compound, aluminum chloride or antimony chloride or the tadiation of ultraviolet rays, serves to moderately anticipate the reaction of scheme B?

After completion of the reaction, the subject compound (1) can? be recovered from the reaction solution directly by evaporation of the solvent or possibly by addition to the reaction solution of water and / or an appropriate organic solvent such as benzene, chloroform, ether or tetrahydro furan for fractional extraction.

The details of the method according to scheme B are indicated more? forward in examples 5 * 6 and 15-17? Scheme C

Yn H Yn

R.

(VI) (VII) (I)

In formula (VI), X, Y, m and n have the same meaning given up to here * In formula (VII), R? one of the groups defined above other than the hydrogen atom and D stands for a halogen atom. When the R group to be introduced in the starting compound (Vi)? an alkyl group, the reagent of the formula (VII) pu? being a di-alkyl sulfate of the formula

RO

SO'2

RO-- "" "

where R? an alkyl group.

Hence the compounds of the formula (VII) can include alkyl halides, acyl halides, dialkyl sulfates, alkenoyl halides and alkenyl haloformates. These compounds can be easily produced by conventional methods per se known *

The reaction between compound (VI) and compound (VII) according to scheme C pu? be made in the absence of any solvent, but preferably in the presence of an organic solvent that can? be an excess of compound (VII) itself. Examples of solvents to be used include hydrocarbons, halogenated hydrocarbons, ethers, esters, ketones, acid amides, alcohols and dimethyl sulfoxide? The acid binder to be used in? the reaction includes organic amines such as triethylamine and pyrid? na and bas? inorganic as the carbonate d? potassium? The reaction can? be carried out at room temperature or conveniently at a high temperature? The reaction time required will obviously depend on the nature of compound (VII) used, the nature of the solvent if used, and the reaction temperature employed, although this can be reduced when the reaction is used. made in a polar organic solvent?

For recovery of the subject compound after completion of the reaction, the resulting reaction solution can be filtered to remove mixture of the acid binder precipitated therein and the filtrate can be evaporated to leave the desired compound? In some cases it can? be added to the reaction mixture water and / or a suitable organic solvent such as benzene, chloroform, ether and tetrahydrofuran to extract the subject compound? Details of the method referred to in scheme C are given more? forward in examples 7-9, 18-20 and 23? Scheme D

C = 0 R'NCO 'C? 0 Yn

H CONHR?

(VI) (VIII) (IX)

In formulas (VIII) and (IX)? R 'stands for alkyl group or optionally substituted phenyl group? So, the method indicated in diagram D? suitable for the preparation of the compounds of formula (I) y in which R raj> has the alkylaminocarbonyl group or the optionally substituted phenylaminocarbonyl group? The reaction between compounds (VI) and (VIII) pu? be made in the absence of any solvent / but preferably in the presence of an organic solvent that can? be an excess of the compound (VIII) itself? The solvent to be used must be inert with respect to the compounds (VIII) under the reaction conditions and includes, for example, hydrocarbons, silo hydrocarbons, ethers, esters and ketones. If a small quan tit? of organic amine such as triethylamine or hydrogen? present as a catalyst, does the reaction proceed very smoothly? The reaction can? be conducted satisfactorily at room temperature or possibly at an elevated temperature. The duration required for the reaction will depend? the nature of the compound (VIII) used and other reaction conditions, although the reaction can normally be completed in a relatively short time.

After the completion of the reaction, the subject compound can? be isolated from the reaction mixture by filtering the crystals of the precipitated compound or by evaporation of the solvent as appropriate? The method d? referred to in scheme D? illustrated more? in detail with reference to examples 10 and 21.

According to a further aspect of this invention, therefore, a process is provided for preparing a compound d? general formula (I) according to claim 1f which comprises:

(a) the reaction of a compound of formula

(II)

wherein X, Y, m, n and R are defined in claim 1, with a carbonyl compound of formula

(III)

in which A and B, which may be the same or different, each represent a halogen atom or an alkoxy, haloalkoxy, alkylthio or animine group?

(b) the halogenation of a compound with formula

Xm

(IV)

R.

wherein Xf m and R are defined in claim 1, Z represents a halogen atom and p? 0, 1 or 2 to produce a compound of formula (I) bearing in the benzene ring a halogen or halogens, the number of which? greater than one unit? with respect to that of the halogen or halogens in the starting compound having formula (IV) J

(c) the reaction in the presence of an acid ligand of a compound having the formula:

(YOU)

wherein X, Y, m and n are defined in claim 1, with a compound of formula:

R D (VII) where R? as defined in claim 1, except for the hydrogen atom, and D represents a halogen atom, or with a di-alkyl sulfate of the formula:

? 3?

where R? an alkyl group, to produce a compound of formula (I) yin which R? different from the hydrogen atom; or

(d) the reaction of a compound d? formula (VI) above with an isocyanate compound having formula R? NCO (VIII) in which R * represents an alkyl group or an optionally substituted phenyl group? to produce a compound of formula (I) in which R? a group -CONHR ??

Are the compounds of this invention highly active against a wide range of fungal and bacterial diseases? including particularly the following:

Perjcularla oryzae (blast) of rice Pellicularia sasaki (sheath bllght) of rice Cochiliobulus miyabeanus (brovn spot) of rice Xanthomonas oryzae (bacter? Al leaf blight) of r? So Aiternaria kikuchiana (black spot) of pear SIornereila cinquiata (ripe rot) of the vine

Adosporium fulvum (leaf mold) of tomato Phytophtora infestans (late blight) of tomato Sclerotinia sclerotiorum (stem rot) of green beans Sphaerotheca fuligenea (povdery mildev) of cucumber Fusarium oxysporum (fusar? Um vilt) of cucumber Pseudoperonnyospora cubensis (dovetronnyospora cubensis) of cucumber Colletotrichum lagenarlum (anthracnose) from cucumber Ervinia aroidea (soft rot) from Chinese cabbage? Are some of the compounds particularly active as seed fertilizers for example, against Glbberella fujikuroi (Bakanae discase or fusariosis pe dale) and against Cochiiliobolus migabeanus of rice? The compounds of the invention are active not only to combat the aforementioned fungal and bacterial diseases for applications in agriculture and horticulture, but also to control the growth of many fungi and bacteria capable of deteriorating industrial materials. So, when the compounds are applied to general industrial products such as paints, lumber, paper, pulp, textiles, cosmetics, leathers, ropes, plastics, rubbers and adhesives,? Is it possible to prevent the deterioration or decay of products that may otherwise be caused by fungi and bacteria?

The compounds can be used as such for fungicidal and bactericidal purposes but they are more? suitably formulated in the compositions for each use? Quj? does this invention, therefore, also provide a fungicidal or bactericidal composition for non-medical use, comprising a compound of general formula (i) above as an active ingredient, in association with a carrier or diluent for the active ingredient? This invention further provides a method for controlling the growth of fungi and bacteria in a plant or industrial material, the method of which includes applying a compound having general formula (I) to the plant or industrial material or in the place of plant what? infested or is it likely to become infested with fungi and bacteria?

For the purposes described above, the compounds of this invention are preferably used in the form of a composition? The type of compositions used in each case will depend? by the particular purpose considered?

The compositions may be in the form of spray powders or granules comprising the active ingredient and a solid diluent or carrier, for example, kaolin, bentonite, kleselguhr, dolomite, calcium carbonate, talc, clay, powdered magnesia, earth Fuller, chalk, Hewitt's earth and diatomaceous earth. The seed dressing compositions, for example, may comprise an agent (e.g., a mineral oil) to facilitate adhesion of the composition to the seed *

Can the compositions also be in the form of dispersible powders or grains comprising a wetting agent to facilitate dispersion in liquids of the powder or grains which may also contain fillers and suspending agents?

The aqueous or emulsifying dispersions can be prepared by dissolving the active ingredient (s) in an organic solvent optionally containing a wetting, dispersing or emulsifying agent (s) and then adding to the mixture water that can be used. also contain wetting, dispersing or emulsifying agent (s)? Suitable solvents are dimethylsulfoxide, dimethylformamide, formamide and alitatic alcohols?

The compositions to be used as sprays can also be in the form of aerosols in which the formulation? contained in a pressurized container in the presence of a propellant, for example, fluorotrichloromethane or dichlorodlfluoromethane.

The different compositions can be better adapted to the different utilities? including suitable additives, for example additives to improve distribution, adhesive power and rain resistance on the treated surfaces? The active ingredient can? be used in the form of mixtures with fertilizers (e.g. fertilizers containing nitrogen or phosphorus)? The compositions can also be used in the form of liquid preparations for use as drops or sprays, which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more. wetting, dispersing, emulsifying or suspending agents. These agents can be cationic, anionic or non-ionic.

Suitable cationic agents are quaternary ammonium compounds, for example, cetyltri-methylammonium bromide. Suitable anionic agents are soaps, salts of alitatic monoesters of sulfuric acid (e.g. sodium lauryl sulfate), and salts of sulphonated aromatic compounds (e.g. sodium dodecylbene nesulfonate, sodium lignosulfonate, calcium or ammonium, butylnaphthalene sulfonate, and a mixture of diisoprop; rl and sodium triisopropyl-naphthalene sulfonates). Suitable nonionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol or ethyl alcohol, or with alkyl phenols such as octylphenol, nonyl phenol and octylcresol. Other non-ionic agents are the partial esters derived from long-chain fatty acids and exitol anhydrides, the condensation products of the said partial esters with ethylene oxide, and the lecithins. Suitable suspending agents are hydrophilic colloids (e.g. polyvinylpyrrolidone and sodium carboxymethylcellulose), and vegetable gums (e.g. acacia gum and tragacanth.

The compositions for use as aqueous dispersions or emulsions are generally provided in the form d? a concentrate containing a high proportion of the active ingredient, the concentrate being diluted with water prior to use. These concentrates should often be able to withstand storage for prolonged periods of time and after such storage be able to dilute with water in order to form aqueous preparations which remain homogeneous for a sufficient time, so as to be conveniently made suitable for application. by means of conventional spray equipment. The concentrates can conveniently contain from 10 to 95%, generally from 25 to 60% by weight of the active ingredient. Such preparations, once diluted to form aqueous preparations, can contain different quantities? active ingredient dependent on the proposed purpose, but can? an aqueous preparation containing from 1 x 10% to 10% by weight of the active ingredient be used.

When the composition of this invention? in the form of fine powder to be sprayed or granules, it is generally applied as such to the plants to be treated for a quantity? which varies from 2 to 4 kg per 10 are (or for a quantity from 10 to 1000 g of active ingredient per 10 are). When the composition? in the form of wettable powder, emulsifiable concentrate, or fluid preparation, this is generally diluted with water before use, to give a concentration of active ingredient of 10 - 5000 ppm, the diluted formulation being generally applied to plants for a quantity ? between 50 and 300 1 for 10 ares. For the treatment of ind? a formulation is applied comprising from 10 to 5000 ppm of active ingredient, at an appropriate rate, which can? vary over a wide range of values.

The compositions of this invention can also comprise other (one or more) compounds having activity? biological, for example other known fungicides, bactericides, plant growth regulators, herbicides and insecticides. In particular, some compounds have been shown to acquire a remarkable synergistic effect once used in mixture with certain known fungicides, how can it be possible? ascertain from the results given more? forward in example 47?

Examples of fungicides and bactericides which may be used in admixture with the compounds of this invention include the following: Carbamate fungicides such as 3,3 '- ethylene bis (tetra hydro-4 * 6-dimesyl-2H-1, 3 , 5-thiadiazine-2-thione), zinc or manganese ethylene bis (dithiocarbamate), bis (dime tildithiocarbammoyl) disulfide, zinc propylene bis (dithiocarbamate), bis (dimethyldithiocarbammoyl) ethylene diamine; nickel dimethyl dithiocarbamate, methyl 1- (butylcarbammoyl) -2-benzimidazolocarbamate, 1,2-bis (3-methoxycarbonyl-2-thioureide) benzene, 1-isopropyl carbamali- 3- (3,5-dichlorophenyl} hydantoin, potassium N- hydroxymethyl-N-methyldithiocarbamate and 5-methyl-10-butoxycarbonylamino-10.1 1-dehydroidibenzo (b, f) aze pina; pyridine fungicides such as zinc bis (l-hydro_s si-2 (iH) pyridinationate) and 2-pyridinatlol -l-sodium salt oxide; phosphorus fungicides such as 0,0-diiso propyl 5-benzylphosphorothionate and O-ethyl S, S-diphenyldi ^ thiophosphate; phthalimide fungicides such as N- (2,6-die tylphenyl phthalimide and N - (2,6-diethylphenyl) -4-methylfta limmide; dicarboximide fungicides such as N-trichloro methylthio-4 ~ cyclohexene-1, 2-dicarboximide and N-tetra-chloroethylthio-4-cyclohexene-1,2-dicarboximide; fungi cides oxatin such as 5,6-dehydro-2-methyl-1,4-oxate ^ na-3-carboxanilido-4,4-dioxide and 5,6-dehydro-2-methyl - 1,4-QSsatin-3 -carboxianilide and 5,6-dehydro-2-methyl - 1,4-oxatin? 3-carboxanilide; naphthoc fungicides hji none such as 2,3-dichloro-1,4-naphthoquinone, 2-oxo-3-chloro-i, 4-naphthoquinone copper sulfate; pentachloronitro benzene; 1,4-dichloro-2,5-dimethoxybenzene; 5-methyl - 5-triazol (3,4-b) benzothiazole; 2- (ti? Cyanomethylthio) benzothiazole; 3-hydroxy-5-methyloxyxazole; N-? 2,3? dichlorophenyltetrachlorophthalanunic acid; 5-ethoxy-3-trichloromethyl-1-2, 4-thiadiazole; 2,4-dichloro-6- (O-chloroanilino) -1, 3,5-triazine; 2,3-dicyano-1,4-dithioan traquinone; copper 8-quinolinate; polyoxin; varidamji china; cyclohexyramide; iron metanoarsonate; diisepropyl-1f3-dithiolane-2-iridene-malonate; 3-allyloxy - 1,2? Benzoisothiazole-1,1-dioxide; kasugamieina; Bla sticidin S; 4,5,6,7-tetrachlorophthalide; 3- (3,5-dichlorophenyl) -5-ethenyl-5-methyloxazolysine-2,4-dione; N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane? 1,2-dicarboxyde; S-n-butyl-S'-para-t-butylbenzyl-N-S-pyridylthiocar bonylimidate; 4-chlorophenoxy-3,3-dimethyl-1-OH, 1,3,4 - triazol-1-yl) -2-butanone; methyl? D, L-N- (2,6-dimethyl ^ phenyl) -N- (2 <,> - methoxyacetyl) alaninate; N-propyl-N- [2- (2,4,6-trichloropheno3si) ethyl-imldazol-1-carboxamide; N- (3,5-dichlorophenyl) succinimide; tetrachloroisophthalate nitrile; 2-dimethylamino-4-methyl-5-n-butyl-6-hydroxy ^ pyrimidine; 2,6-dichloro-4-nitroaniline; 3-methyl-4-chlorobenzothiazole-2-one; 1,2,5,6-tetrahydro-4H-pyrol- 1, 3,2,1-1, quinoline-2-one; 3'-13opropoxy-2-methyl benzalinide; 1- ^ 2- (2,4-dichlorophenyl) -4? Ethyl-1,3-dio ^ sorane-2-ylmethyl -1H, 1,4-triazole; 1,7-benzisothia zolina-3-one; basic copper chloride; basic copper sulfate} IM-dichlorofluomethylthio-NjN-dimethyl-N-phenylsol-fammide; ethyl-N- (3-dimethylaminopropyl) thiocarbamate hydrochloride} pyomycin; S, s-6-methylquinoxaline-2,3-diyldithiocarbamate; complex of zinc and maneb; di -zinc-bis (diraethyldithiocarbamate) ethylene bis (dithium carbamate)?

Examples of plant growth regulators and herbicides which can be used in combination with the compounds of this invention include the following. - iso urea-based plant growth regulators such as N-methoxycarbonyl-N'-4-methylphenylcarbamil ^ ethylisourea and 1- (4-chlorophenylcarbamyl) -3-ethoxycarbonyl-2-methylisourea; another type of plant growth regulators such as sodium naphthalene acetate, 1,2-dehydropyridazine-3 * 6-dione and gibberellins; triazine-based herbics such as 2-methylthio-4 * 6-bisethylammyl no-1,3,5-triazine, 2-chloro-4,6-bisethylamino-1,3,5-triazine, 2-methoxy-4 -ethylamino-6-isopropylaminor1,3,5 - triazine, 2-chloro-4-ethylaramino-6-isopropylamino-s - triazine, 2-methylthi? -4,6-bis (isopropylamino) -s-tria zina e 2-methylthio-4-ethylamino-6-isopropylamino-s - triazine; phenoxy-herbicides such as 2,4-dichlorophenoxy acetic acid and methyl and butyl esters thereof, 2-chloro-4-methylphenoxyacetic acid, 4-chloro - 2-methylphenoxyacetic acid and ethyl 2-methyl-4-chlorophenoxy_ C_> butylated ; diphenylether based herbicides such as 2,4,6 - trichlorophenyl-4 '-nitrophenyl ether, 2,4-dichlorophenyl-? p -4 * -nitrophenylether and 3,5-dimethylphenyl-4'-nitrophenyl ether; urea herbicides such as 3- (3,4-dichlorophenyl) - sa -1-methoxy-1-methyl urea, 3- (3f4-dichlorophenyl) -1,1 - diraethylurea and 3- (4-chlorophenyl) -l , 1-dimethyl urea; for carbamate bicides such as 3-methoxycarbonylaminophenyl? N- (3-methylphenyl) carbamate, isopropyl-N- (3-chloro

phenyl) carbamate and methyl? N- (3f4? -dichlorophenylJcarbam

mato; uracil herbicides such as 5-bromo-3-sec-butyl - 6-methyluracil and 1-cyclohexyl-3,5-propylene uracil; thiolcarbamate herbicides such as S- (4-chlorobenzyl) -N, N - diethylthiolcarbamate, S-ethyl-N-cyclohexyl-N-ethylthiol ^ carbamate and S-ethyl-hexahydro-1H-azepine-1-carbothioate

and S-ethyl-N, N-di-n-propylthiocarbamate; p ^ ridinium herbicides such as 1-1'-dimethyl-4 # 4, -bispiridinium dichloru

ro; phosphoric herbicides such as N- (phosphonomethyl) glyein; aniline herbicides how?,? ,? -trifluoro-2,6-di ^ nitro-N, N-dipropyl-p-toluidine, 4- (methylsulfonyl) -2,6 - dinitro-N, N-dipropyl aniline and N ^, N ^ -diethyl-2 , 4-dini.

tro-6-trifluoromethyl-1 t3-phenylene-diamine; acid anilide herbicides such as 2-chloro-2 *, 6? - diethyl-N- (butos ^ simethyl) aceto anilide, 2-chloro-2'f6'-diethyl-N- (methyllois simetilJaceto anilide, and 3,4 -dichloropropionanilide; piSazole herbicides such as 1,3-dimethyl-4- (2,4-dichloro benzene) -5-hydroxy-pyrazole and 1,3-dimethyl-4 ~ (2,4-dir chlorobenzoyl) -5- ( p-tolueneesulfonyloxy) pyrazole 5-tert-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -1, 3 * 4-bone diazoline-2-onej 2-? N-isopropyl, N- (4-chlorophenyl ) carbamoyl] -4-chloro-5-methyl-4-isoxazoline-3-one; 3-isopropyl-benzo-2-thia-1, 3-diazinone- (4) -2,4-dioxydo and 3- ( methylphenoxy) pyridazine?

Examples of insecticides which can be mixed with the compounds of this invention include the following: -phosphoric insecticides such as 0,0-diethyl 0- (2-isopropyl ^ -4-methyl-6-pyrimidinyl) phosphorothioate, 0,0-diethyl S-2- [(ethylthio) ethyl] phosphorodithioate, 0,0-dimethyl. 0- (3? Methyl-4-nitrophenyl thiophosphate, 0,0-dimethyl S- (N-methyl ^ carbamoylmethyl) phosphorodithioate, 0,0- dimethyl S- (N-me tyl-N-? ormylcarbomoylmethylphosphorodithioate, 0,0-dimethyl S? 2? [(ethylthio) ethyl phosphorodithioate .,0,0-diethyl S-2- [(ethylthio) ethyl phosphorodithioate, 0, 0-dimethyl -1 - hydroxy-2,2,2-trichloroethylphosphonate, 0,0-diethyl-0 - (5-phenyl-3-isoxazolyl) phosphorothioate, 0,0-dimethyl 0- (2,5-dichloro -4-bromophenyl) phosphonothioate, 0,0-dimethyl 0? (3-methyl-4-methyl mercaptophenyl thiophosphate, 0-ethyl 0-p-cyanophenyl phenylphosphonothioate, 0,0-dimethyl-S- (1,2dicarboethoxyethyl) phosphorodithioate, 2- chloro- (2,4,5-trichlorophenyl) vinyl dimethyl phosphate, 2-chloro-1- (2,4-di_chlorophenyl) -vinyldimethyl phosphate, OfO-dimethyl 0-pcyanophenyl phosphorothioate, 2,2-dichloro vinyl dimethyl phosphate, 0,0-diethyl 0-2,4-dichlorophenyl phosphorothioate, ethyl mereaptophenyl acetate, 0,0-dimethyl phosphorodithioate, S- [(6-chloro-2-oxo-3-benzooxazolinyl) methyl 0,0- -dethyl phosphorodithioate, 2-chloro-1- (2,4-dichlorophenyl) virile diethylphosphate, 0,0-diethyl 0- (3-oxo-2-phenyl-2H-pyridazine-6-yl-phosphorothioate,?,? -dimethyl s- (1-methyl - 2-ethyl-sulfinyl) -ethyl phosphorothioate, 0,0-dimethyl S - phthalimido methyl phosphorodithioate, 0,0-diethyl S- (N - ethoxy-carbonyl-N-me tylcarbamoylmethyl) phosphorodithioate, 0,0-dimethyl S- [2-methoxy-1,3,4-thiadiazole-5- (4H) - onyl- (4) -methylJ dithiophosphate, 2-methoxy-4H-1,3 , 2-ben zooxaphosphorine 2-sulfide, 0,0-diethyl 0- (3,5,6-triclo ro-2-pyridyl) phosphorothioate, 0-ethyl 0-2,4-dichlorophenyl thionobenzene phosphonate, S- [4, 6-diamino-s-triazine - 2-yl-methyl] 0,0-dimethyl phosphorodithioate, 0-ethyl 0-p - nitrophenyl phenyl phosphonothioate, 0, S-dimethyl N-acetyl phosphoroamidothioate, 2-diethylanunino-6- methylpyrimidine - 4-yl-diethylphosphorothioate, 2-diethylamino-6-methylpi ^ rimidine-4-yl-dime tylphosphorothioate, 0,0-diethyl 0-p - (methylsulfonyl) phenyl phosphorothioate, 0-ethyl S-propyl 0-2,4-dichlorophenylphosphorodithioate and cis-3- (dimethoxy phosphenoxy) N-methyl-cis-crotoneamide; carbamate insecticides such as 1-naphthyl N-methylcarbamate, S-methyl N- [methylcarbamoyl-oxy] thioacetoimidate, m-tolyl methylcarbamate, 3,4-xylyl methylcarbamate, 3,5-xylyl methylcarbamate, 2-sec-butylphenyl N-methylcarbamate 2,3-dihydro? 2,2? Dimethyl-7? Benzofuranylmethylcarbamate, 2-isopropoxyphenyl N-methylcarbamate, 1,3-bis (carba ^ moylthio) -2 (?,? - dimethylanimino) -propane hydrochloride and 2-diethylamino- 6-methylpyrimidine-4yl-4imethylarbath; and other insecticides such as?,? - dimethyl N * - (2-methyl - 4-chloro? enyl) formamidine hydrochloride, nitrogen sulfate, milbemycin, 6-methyl-2,3-quinoxalinadithioc1 helix S, s-dithiocarbanate , 2,4-dinitro-6-sec-butylphenyl dimethylacrylate, 1,1-bis (p-chlorophenyl) 2,2,2-trichloroethanol, 2- (p-tert-butylphenoxy) isop? Opyl-2? - clo ? oethylsulfite, azoxybenzene, di- (p-chlorophenyl) - cyclopropll carbinol, di? tri (2,2-dimethyl-2-phenji letyl) tin] oxide, 1- (4-chlorophenyl) -3- (2,6 -difluo robenzoyl) urea and S-trichlorohexyltin 0,0-diisopro pylphosphorodithioate?

This invention? further illustrated but not limited by the following examples, in which percentages and parts are all by weight?

Example 1

Preparation of the No 1 compound of Tab? 1 (Scheme A) 2lt3g of 2-amino-4,5,6-trichlorophenol. , 27.6 g of anhydrous potassium carbonate and 150 ml of toluene were placed in a round bottom flask of the capacity? of 300 ml and 9.9 g of phosgene were slowly introduced into the mixture with stirring under cooling in a chilled water bath. The resulting mixture was heated to reflux temperature for a? and the reaction solution was then cooled and transferred to a 500 ml separating funnel. 150 ml of tetrahydrofuran and 150 ml of water were added to the funnel and the organic layer was separated, dried with anhydrous sodium sulfate and filtered. The filtrate was evaporated to remove the solvent, leaving yellowish white crystals. The crystals were recrystallized from a mixed solvent of methanol and acetone to give 22.7 g of 5,6,7-trichloroben zoxazolone in the form of white crystals having a point of fusion of 253-254eC.

Example 2

Preparation of compound No 1 (scheme A)

21.3 g of 2-amino-4,5,6-trichlorophenol, 27 t6 g of anhydrous potassium carbonate and 150 ml of ethylacet? were placed in a 300 ml round bottom flask and a solution of 9.9 g of diphosgene (trichloromethyl chloroformate) dissolved in 50 ml of ethyl acetate was added dropwise to the mixture with stirring under cooling in a chilled water bath. The resulting mixture was heated to reflux temperature for three hours and the reaction solution was then cooled and aspirated to remove insoluble salts. The filtrate was concentrated to dryness under reduced pressure to give yellowish white crystals, which were recrystallized from methanol / acetone to give 19.6 g of 3,6,7-trichlorobenzoxazolone in the form of white crystals with a melting point of 253- 259? C. Example 3

Preparation of compound No 1 (Scheme A)

18.1 g of 2-ethoxycarbonylaminophenol (produced from 2-aminophenol and ethyl chloroformate) were dissolved in 200 ml of acetic acid and 23.4 g of chlorine gas were passed into the solution at a temperature of 8090 ° C? The reaction solution so? obtained was cooled and evaporated to remove acetic acid, leaving 27.9 g of yellow crystals of 2-ethoxycarbonylamino-4,5,6-trichlorophenol which melted at 190-193? C? The crystals were placed, together with 45 ml of dimethylformamide and 0.5 g of anhydrous potassium carbonate, in a 200 ml round bottom flask and the mixture was heated with stirring at 140 ° C for 4 hours. After cooling the resulting solution, 100 ml of water was added to the latter to precipitate the crystals, which were then separated by suction filtration and dried in air for 2 hours to give pale yellow crystals. Recrystallization from methanol / acetone yielded 19.1 g of white 5,6,7-trichlorobenzoxazolone crystals with a melting point of 253-254 ° C.

Example 4

Preparation of compound No 3 of Tab. 1 (Scheme A) 10.9 g of 0-aminophenol and 100 ml of acet: L co acid were placed in a 300 ml round bottom flask, followed by the addition of 10.2 g of acetic anhydride under cooling with chilled water that is? frozen. The mixture was heated at 60 ° C for one hour to complete the reaction resulting in the formation of 2-acetaminophenol. 23.4 g of chlorine gas was then passed into the reaction mixture at a temperature of 8o-90 ° C and the resulting reaction solution was cooled and evaporated under reduced pressure to leave 24.9 g of yellow 2-acetamino crystals. 4,5,6-trichlorophenol which fused with decomposition at 200 ° C.

The crystals were placed in a 300 ml round bottom flask, to which 150 ml of tetrahydrofuran was added followed by 9.6 g of sodium hydride [50% suspension in oil). 9.9 g of phosgene were then introduced into the mixture under cooling with chilled water, i.e. ice and the resulting mixture was stirred at room temperature for one hour. * The reaction solution was transferred to a separator tube, into which 150 ml of benzene and 150 ml of water were added and the organic layer was separated, dried with anhydrous sodium sulfate, and filtered. Was the filtrate evaporated to remove the solvent, leaving yellow crystals? The crystals were recrystallized from a solvent formed from a mixture of hexane and acetone to give 25.2 g of N-acetyl-5,6,7-trichlorobenzoxazo ion in white crystals, having a melting point of 171-172 ° C.

Example 5

Preparation of compound No 1 (scheme B)

20.9 g of 5,7-dichlorobenzoxazolone and 150 ml of acetic acid were placed in a 300 ml round bottom flask and the mixture was heated to 8o-90 ° Cf followed by the passage of 7.8 g of chlorine gas. ? The reaction solution was concentrated by evaporation of the acetic acid to obtain yellow crystals. Recrystallization from methanol / acetone yielded 23.4 g of white 5,6,7-trichloro benzoxazolone crystals with a melting point of 253-254 ° C. Example 6

Preparation of compound No? 3 (Scheme B)

24.6 g of N-acetyl-5,7-dichlorobenzoxazolone and 150 ml of chloroform were placed in a 300 ml round bottom flask, and 16.5 g of sulfuryl chloride was then added to them at room temperature. The mixture was heated to reflux temperature for two hours and the reaction solution was so. obtained was evaporated under reduced pressure to leave yellow crystals. Recrystallization from hexane / acetone yielded 26.6 g of white N-acetyl-5,6,7-trichloro benzoxazolone crystals with a melting point of 171-172? C? Example 7

Preparation of the compound No? 2 in Table 1 (scheme C) 4.8 g of 5,6,7-trichlorobenzoxazolone, 2.8 g of anhydrous potassium carbonate, 2.5 g of dimethyl sulfate and 50 ml of acetone were loaded into a flask 100 ml spherical material and the contents of the flask were heated under reflux for 2 hours. Thereafter, the reaction solution was evaporated under reduced pressure and the residue was collected in 50 ml of water. The solution was filtered to give yellowish brown crystals, which were recrystallized from acetone to give 9.8 g of yellow N-methyl-5,6,7-tryclo robenzoxazolone crystals with a melting point of 135-139? C. Example 8

Preparation of Compound No, 8 in Table 1 (Scheme C) 4.8 g of 5,6,7-trichlorobenzoxazolone, 2.0 g of triethyl amine and 50 ml of acetone were placed in a 100 ml round bottom bottle. , in which 2.8 g of benzoyl chloride were then added dropwise under cold cooling in chilled water, that is? icy and shaking. After completion of the addition, the resulting mixture was heated under reflux for one hour to complete the reaction, after which the reaction solution was cooled and filtered to move the precipitated salts. The filtrate was evaporated to leave white crystals, which were recrystallized from hexane / acetone to give 6.5 g of white N-benzoyl-5,6,7-trichlorobenzoxazolone crystals with a melting point of 188-190 ° C.

Example 9

Preparation of compound No. 10 in Tab. 1 (Scheme C) Following the same procedure described in example 8, except Ail benzene chloride was replaced by 1.9 g of methylchloroformate, 5.7 g of N-methoxy carbonyl-5.6 , 7-trichlorobenzoxazolone were obtained as yellowish white crystals with a melting point of 163-164 ° C,

Example IO

Preparation of compound No. 14 in Table 1 (Scheme D) 4-8 g of 5,6,7-trichlorobenzoxazolone, 3,8 g of 3,5-dichlorophenylisocyanate, 50 ml of acetone and three drops of triethylamine were placed in a 100 ml round bottom flask and the mixture was stirred at room temperature for one hour. The precipitate was separated by filtration to give 7.7 g of pale yellow crystals which were identified as N-3,5-dichlorophenylcarbamoyl-5,6,7-trichlorobenzoxazolone at the melting point of 235- 237? ^.

Example 11

Preparation of compound No. 25 in Tab? 1 (Scheme A) The procedure of Example 1 was repeated starting with 15.8 g of 2-amino-4-chloro-6-methylphenol instead of 2-araino-4,5,6-trichlorophenol? Recrystallization of the raw brown crystals from hexane / acetone gave 15.6 g of 5-chloro-7-methylbenzoxazolone as yellowish brown crystals of 232-234 ° C melting point.

Example 12

Compound Preparation No, 67 (Scheme A)

The procedure of Example 2 was repeated starting with 21.2 g of 2-amino-3? 5-dimethyl-4,6-dichlorophenol instead of 2-amino-4,5,6-trichlorophenol. Were they obtained in this way? 20.9 g of 4,6-dimethyl-5,7-dichloro benzoxazolone in the form of pale yellow crystals with a melting point of 271-272 ° C *

Example 13

Preparation of Compound No, 1 (Scheme A)

23.0 g of 2-ethoxycarbonylamino-4-methyl-5-chlophenol (prepared from 2-amino-4-methyl-5-chlorophen 10 and ethyl chloroformate) were placed in a 100 ml round bottom flask, 50 ml of dimethylformamide and 0.5 g of anhydrous potassium carbonate, and the mixture was heated with stirring at 140 ° C for 4 hours. The resulting reaction mixture was cooled and poured into 100 ml of water to separate the crystals, which were collected by suction filtration and dried in air at 8 ° C for 2 hours to give yellow crystals. Recrystallization of the latter from methanol produced 15.6 g of pale yellow crystals of 5-methyl-6-chlorobenzoxazolone with a melting point of 182-184 ° C,

Example 14

Preparation of compound No, 52 in Tab, 1 (Scheme A) By means of the procedure described in example 4, 24.5 g of N-acetyl-5-isopropyl-6,7-clicloroben zoxazolone in the form of yellowish brown crystals (melting point 133-135 * 0) were prepared from 15.1 g of 2-amino-4-isopropylphenol by means of a dark oil (25.7g) of 2-acetamino-4-isopropyl-5.6-- dichlorophenol.

Example 15

Preparation of Compound No, 31 in Tab. 1 (Scheme B) The procedure of Example 5 was repeated but 18.4 g of 5-chloro-7-methylbenzoxazolone were used instead of 5.7-dichlorobenzoxazolone, to produce 20.7 g of 5,6-dichloro-7-methylbenzoxazolone as pink crystals having a melting point of 251-252 ° C.

Example 16

Preparation of Compound No. 54 (Scheme B)

18.4 g of 5-chloro-7-methylbenzoxazolone and 150 ml of acetic acid were placed in a 300 ml round bottom flask and 17? 6 g of a 30 ml bromine solution were added to the mixture in drop form. ml of acetic acid. The resulting mixture was heated to 95 ° C and stirred at that temperature for 4 hours. Then the reaction solution was cooled to room temperature and concentrated by evaporation of the acetic acid to give pink brown crystals, which were recrystallized from methanol / vinegar to produce 22.3 g of 5-chloro-6-bromo-7 methylbenzoxazolone in form of brown crystals with a melting point of 262-269 ° C.

Example 17

Preparation of compound No. 64 (scheme B)

The procedure of Example 6 was repeated using for? 26.0 g of N-acetyl-4-methyl-5,7-dichlorobenzos sazolone instead of N-acetyl-5 # 7-dichlorobenzoxazolone, to give 23.6 g of the corresponding derivative of 5,6,7 - trichloro in form of white crystals having a melting point of 125-127 ° C.

Example 18

Preparation of the compound No, 32 in Tab? 1 (scheme C) The procedure of Example 7 was repeated using for? 4.4 g of 5,6-dichloro-7-methylbenzoxazolone instead of 5,6,7-trichlorobenzoxazolone, to produce 3.9 g of N-methyl-5,6-dichloro-7-methylbenzoxazolone in the form of pink crystals with a melting point of 122-123? C?

Example 19

Preparation of compound No. 35 in Tab, 1 (Scheme C) 4.4 g of 5,6-dichloro-7-methylbenzoxazolone, 2.8 g of benzolichloride and 50 ml of acetone were placed in a 100 ml, into which 2.0 g of triethylamine were then added dropwise under cooling with chilled water, i.e. icy and shaking. After completion of the addition, the resulting mixture was heated under reflux for one hour to complete the reaction, after which the reaction solution was allowed to cool and filtered to remove precipitated salts. The filtrate was evaporated to leave yellowish white crystals, which were recrystallized from acetone to give 5.5 g of white N-benzoyl-5,6-dji chloro-7-methylbenzoxazolone crystals with a melting point of 165-166 ° C.

Example 20

Preparation of compound No. 37 (Scheme C) Following the procedure relating to example 9 but starting from 4.4 g of 5,6-dichloro-7-methylbenzoxazo ion, 4.6 g of N-methoxycarbonyl? 5 were obtained, 6-dichloro-7-methylbenzoxazolone in the form of pink crystals with a melting point of 135-138 ° C.

Example 21

Preparation of Compound No. 41 (Scheme D) Following the procedure defined in Example 10 but starting from 4.4 g of 5,6-dichloro-7-methylbenzos-sazolone, 7.4 g of N-3 were obtained, 5 ~ dichlorophenyl ^ carbamoyl-5,6-dichloro-7-methylbenzoxazolone in pink crystal form of melting point of 221-222 ° C.

Example 22

Preparation of Compound No. 69 (Scheme A)

Was the procedure of example 1 repeated but replacing 2? amino-4, 5, 6-tr lei orophenol with 22.6 g of 3-chloro-6-acryloylamino-2,4-xylenol (produced from 3 -c 1 or 0-6- herons n o-2, 4- xylenol and acryloyl chloride). The recrystallization of the yellow-raw crystals? from acetone said 20.4 g of yellowish white crystals of N-acryloyl-5, 7-dimethyl-6-chlorobenz / oxazolone having a melting point of 161-163 ° C.

Example 23

Preparation of Compound No. 70 (Scheme C) Following the same procedure as in Example 19 but using 23.9 g of 5,6,7-trichlorobenzoxazolone, 12.0 g of allyl chloroformate and 10.1 g of triethylamine, 27.4 g of N-allyloxycarbonyl-5, 6,7-trichlorobenzoxazolone were obtained in the form of light yellow crystals with a melting point of 96-98 ° C. Example 24

Concentrated emulsifiable formulation

An emulsifiable concentrate comprising 20% of the active ingredient was produced by uniformly mixing the ingredients listed below and stirring the mixture until all ingredients were dissolved.

Compound Parts No, 10 20

Dime thylformamide 30

Xylene that is? Xylene 35 Polyoxyethylene alkyl aryether 15 Similar emulsifiable concentrates comprising 20% of compound No. 36 or No. 69 as the active ingredient were prepared in the same manner as indicated above.

Example 25

Oily formulation

An oily formulation was prepared by mixing 10 parts of Compound No. 1 and 90 parts of ethyl cello solve (2-ethoxyethanol) and stirring the mixture until these ingredients were dissolved.

Example 26

Fluid formulation

A fluid (free flowing) formulation comprising 40% of the active ingredient was prepared by uniformly mixing together the following ingredients:

Compound No. 4 (ground to size

of particles below 10 /? ) 40 Lauryl sulfate 2 Sodium alkyl talenesulfonate

Hydroxypropyl cellulose 1

Water 55

Similar formulations comprising 20% of compound No. 32 or No. 70 as the active ingredient were prepared in the same manner as described above.

Example 27

Water dispersible powder formulation A water dispersible powder was produced by uniformly mixing the ingredients listed below and then grinding the mixture.

Parts Compound No. 3 20 Polyoxyethylene alkyl aryl ether, 5 Calcium lignosulfonate 3 Kieselguhr 72 Similar water dispersible powders comprising 20% of compound No. 48 or No. 69 as active ingredient were prepared in the same manner as indicated above. ? over.

Example 28

Fine powder formulation

Was a fine powder obtained that? sprayable by uniformly mixing the ingredients listed below and grinding the resulting mixture.

Parts Compound No. 5 3 Fine Silica Powder 0.5 Calcium Stearate 0.5 Clay 50

Talc 46 Similar fine powders comprising compound No. 53 or No. 70 as the active ingredient, were prepared in the same manner as indicated above. Example 29

Granular formulation

A composition in the form of granules was prepared by uniformly mixing the ingredients listed below and then granulating the mixture in the presence of added water. The resulting mixture was dried and passed through a sieve to obtain the desired grain size.

Parts Compound No. 6 5 Calcium Lignosulfonate 1 Bentonite 30 Clay 64 Similar granular formulations comprising 5% of compound No. 24 or No. 70 as the active ingredient were produced in the same manner as described above.

Example 30

Bagnabjle powder formulation

Was a wettable powder made by mixing the ingredients listed below together and grinding the mixture?

Parts Compound No. 10 20 N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide 20 Polyoxyethylene alkyl aryether 5 Calcium lignosulfonate 3 Kieselguhr 52 Example 31

In this example, the benzoxazolone derivatives of this invention were tested against a variety. of fungal and bacterial diseases of plants. The tests were conducted according to the standard agar dilution method. The culture medium used was potato dextrose agar (pH 5.8) for fungi and agar broth (pH 7.0) for bacteria. The medium containing an acetone solution of the required concentration of the active ingredient was inoculated by means of a platinum ring with a spore suspension obtained by adding sterilized water to the test microorganisms which had been incubated on a slope of the medium in a tube of

trial. Further incubation of the inoculated medium was carried out for 48 hours at 24 ° C for mushrooms and at 28 ° C for

bacteria. Then the growth of the microorganisms was observed and the minimum inhibitory concentrations (MIC, / # g / ml) of the test derivatives were determined.

The test results are shown below in Tab.

2. In the tables shown from here on, the controls

li A, B, C and D indicate use as an active ingredient

of the following compounds, described in the listed literatures

A: (German Patent N? 1,023,627) CI or X

CI CI

B: .ci \ (German patent No. 1,147.007) CI O /

THERE

C: o c = o (Japanese Patent Publication No. 23,519 / 65)

Cl

CI co

D: Cl (Japanese Patent Publication or \

c? 0 No. 23.519 / 65)

Cl X

Cl co <dy

6o ~

Tab 2

Compound No. in Tab MIC (ug / ml)

Disease and plant

Fusarium oxysporura

('Cucumber ^ <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <5 <5 <5 Cladosporium fulvum

(Tomato) <2.5 <5 <2.5 <2.5 <5 <2.5 <5 <5 <5 Gibberella fujikuroi

(Rice ") <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 Glomerella cingulata

(Screw) <1.25 <2.5 <2.5 <2.5 <2.5 <2.5 <5 <5 <or Aiternaria klkuchiana

(Pear) <5 <5 <5 <5 <5 <5 <5 <5 <10 Piricularia oryzae

(Rice) <1.25 <1.25 <1.25 <1.25 <1.25 <1.25 <2.5 <5 <5 Cochliobolus miyabeanus

(Rice) <2.5 <2.5 <1.25 <1.25 <2.5 <1.25 <2.5 <2.5 <5 Erwinla aroidea?

(Chinese cabbage ^ <2.5 <5 <5 <5 <5 <5 <10 <20 <20 Pseudomonas lachrymans

<10 <10 <10 <10 <10 <10 <20 <20 <20 (Cucumber)

Xantnomonas oryzae

(Rice) <10 <10 <10 <10 <10 <10 <20 <20 <20 Comp? Sto No- ln Tab MIC (yg / mi)

Disease and plant

10 11 12 13 14 15 16 17 Fusarium oxysporura

(Cucumber) <2.5 <2.5 <5 <5 <5 <2.5 <5 <2.5 Cladosporium fulvum

(Tomato) <2.5 <2.5 <2.5 <5 <5 <2.5 <5 <2.5 Gibberella fuj'ikuroi

(Rice) <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 <2.5 Glomerella clngulata

(Screw) <2.5 <2.5 <5 <5 <5 <2.5 <2.5 <2.5 Kikuchian alternate

(Pear) <5 <5 <5 <5 <5 <5 <5 <5 Piricularia oryzae

(Rice) <1.25 <1.25 <2.5 <2.5 <2.5 <1.25 <2.5 <1.25 Cochliobolus mlyabeanus

(Rice) <1.25 <1.25 <5 <5 <5 <1.25 <5 <1.25 Erwinia aroidea

(Chinese cabbage) <2.5 <5 <10 <10 <10 <2.5 <10 <5 Pseudomonas lachrymans

(Cucumber) <10 <5 <10 <10 <10 <5 <10 <10 Xantnomonas oryzae

(Rice) <10 <5 <20 <10 <5 <10 <10 <10 Compound No.l In Tab 1, MIC (pg / nOT

Disease and plant

18 19 69 70 B D

Fusarium oxysporum

(Cucumber) <2.5 <2.5 <2.5 <2.5 <20 <20 <20 <20

Cladosporium fulvum

(Tomato) <2.5 <5 <2.5 <5 <20 <20 <20 <20

Gibberella fujikuro?

(Rice) <2.5 <2.5 <2.5 <2.5 <20 <20 <20 <20

Glomerella cingulata

(Screw) <2.5 <2.5 <1.25 <2.5 <20 <20 <20 <20

Alternate it Kikuchiana

(Pear) <5 <5 <5 <5 <40 <40 <40 <40

Piricularia oryzae

(Rice) <1.25 <1.25 <1.25 <1.25 <20 <20 <20 <20

Cochliobolus miyabeanus

(Rice) <1.25 <1.25 <2.5 <2.5 <20 <20 <20 <20

Erwinia aroidea

(Chinese cabbage) <20 <20 <10 <10 <160 <80 <160 <80

Pseodomonas lachrymans

(Cucumber) <10 <20 <10 <10 <160 <80 <160 <80

Xantnomonas oryzae

(Rice) <10 <10 <10 <10 <40 <40 <40 <40 This example illustrates the activity? benzoxazolone derivatives fungicide against Pjricularia oryzae A powder formulation dispersed in water, prepared as described in Example 27, was diluted with water to produce test formulations containing the required concentrations of the active ingredient. The test formulation was applied to aquatic rice cultures (of the "Asahi" variety, third foliage stage) that had been grown in 9 cm diameter cookie pots within a greenhouse. One day after application, the treated cultures were spray inoculated with a suspension of Pjricularia oryzae spore and incubated in a humid chamber with humidity. relative of 95-100% and at a temperature of 24? 25? C. 5 days after inoculation, the number of wilting lesions per leaf at the third foliage stage was assessed, and disease control was calculated using the following equation: Disease Control (%) =

^ Number of lesions in treated plots Number of lesions in untreated plots 11 disease control? an average value of the results of the tests which were conducted in two replicates at each concentration of the active ingredient. Was phytotoxicity also visually ascertained? with regard to rice plants by means of the following gradations:

Gradations Value of phytotoxicity?

5 Severe damage

4 Great damage

3 Moderate damage

2 Slight damage

1 Negligible damage

No damage

Are the test results shown below in Table 3?

TABLE 3

Compound Concentration Disease Control Phytotoxicity? No. (ppm) _ _ _

200 100

200 78 0

3 200 100 0

4 200 98 0

5 200 94 0

6 200 98 0

7 200 98 o

8 200 100 0

9 200 96 0

10 200 100 0 Compound Concentration Disease control and Phytotoxicity. N? (ppm)? _ _ (#)

11 200 100 0

12 200 92 0

13 200 86 0

14 200 82 0

15 200 98 0

16 200 98 0

17 200 100 0

18 200 100 0

19 200 100 0

20 200 84 0

22 200 92 0

23 200 96 0

27 200 82 0

30 200 98 0

31 200 88 0

33 200 98 0

36 200 98 0

37 200 100 0

38 200 100 1

41 200 98 1

46 200 92 0

47 200 98 0

50 200 98 0

53 200 100 0

61 200 100 0

Compound Concentration Disease Control Phytotoxicity. N? (ppm) _ _ (%) '_ _

62 200 100 0

64 200 98 0

66 200 '96 0

68 200 94 0

69 200 100 0

70 200 100 0

Control A 200 52 1

II B 200 63 2

C 200 30 1

D 200 30 1

IBP

(Cornfcrollo) * 480 75 0

Untreated

0

#IBP: (i - C3H70) ZP -SCH2? (())

Example 33

This example illustrates the activity? of the benzoxazolone derivatives against Cochliobolus miyabeanus.

The tests were conducted with the same procedure as in Example 32, except that the rice cultures at the fourth foliage stage were inoculated with a suspension of d? spore of Cochliobolus m? ^ abeanus The results are shown below in the Tah. 4

f

TABLE 4

Compound Concentration Disease Control Phytotoxicity? No._ (ppm) _ _% _ _

1 500 100 0

2 500 85 1

3 500 100 0

4 500 98 0

5 500 96 0

_ & 9

Compound Concentration Disease Control Phytotoxicity? No . (ppm) _ {%} _ _ _

6 500 100 0

7 500 94 0

8 500 92 0

9 500 88 0

10 500 100 0

11 500 98 0

12 500 94 1

13 500 90 0

14 500 92 1

15 500 86 0

16 500 83 0

17 500 100 0

18 500 100 0

19 500 100 0

20 500 100 0

21 500 98 0

22 500 82 0

23 500 96 0

24 500 76 0

25 500 76 0

26 500 72 0

27 500 88 0

28 500 80 0

29 500 92 0

30 500 88 0

31 500 100 0 Compound Conoentraz ion Control.amatti Phytotoxicity? No. _ <(> ??.? <)> ._ (?)

32 500 96 0

33 500 100 0

34 500 94 0

35 500 96 0

36 500 100 0

37 500 100 0

38 500 98 0

39 500 100 0

40 500 96 0

41 500 100 0

42 500 98 0

43 500 98 0

500 96 0

45 500 88 0

46 500 98 0

47 500 98 0

48 500 76 0

49 500 72 0

50 500 98 0

51 500 82 0

52 500 76 0

53 500 88 0

54 500 94 0

55 500 98 0

56 500 73 0

57 500 88 0 Compound Concentration Disease Control Pitotoxicity No . (*)

58 500 98 0

59 500 100 0

60 500 98 0

61 500 96 0

62 500 100 0

63 500 76 0

64 500 82 0

65 500 80 0

66 500 100 0

67 500 72 0

68 500 100 0

69 500 100 0

70 500 100 0

Control.A 500 32 3

"B 500 54 4

"C 500 25 1

"D 500 30 2

Triazino. *

(Control?) 500 93 0

Untreated 0

THERE

* Triazina ,:

Cl

C1 f "ON ^ <NH> O

Example 34

In this example, were the active compounds tested against Sclerotinia sclerotiorum by the following technique?

A water dispersible powder formulation prepared as described in Example 27 was diluted with water to constitute test formulations containing the required concentrations of the active ingredient. Was the test formulation applied to seedlings of French green beans (of the "Taisho Kin toki" variety) at the stage of the second true leaf, which had been grown in soil in biscuit pots 9 cm in diameter, in a greenhouse? Was the application size 10 ml of formulation for each jar? One day more? later, each leaflet of the two true leaves was inoculated in the center with a piece of agar infected with fungi obtained by piercing the edge of the mushroom cluster Sclerotinia sclerotiorum which had been inoculated in the agar medium using a 5 mm cork bur potato dextrose at 20? C for two days? The inoculated seedlings were then kept in a humid room at 20 ° C for three days in order to allow the development of the disease. Then the length of the lesions by rot was measured with a vernier caliper and the disease control was calculated with the following equation.

Disease control {%) =

Length of lesions in treated areas

= (1 - _) x Length of lesions in untreated areas Disease control? an average value of the results of the tests which were conducted in two replicates at each concentration of the active ingredient. Phytotoxicity? of the green beans was visually ascertained with the same gradation indicated in * example 32.

The results are given in Table 5 below.

TABLE 5

Compound Concentration Disease Control Phytotoxic No._ (ppm) in _

1 500 100 1

3 500 88 0

5 500 86 0

6 500 94 1

10 500 100 0

17 500 89 0

19 500 85 0

Control A 500 43 3

? B 500 48 4

"C 500 26 2 Compound Concentration Disease Control Phytotoxicity No? - -. (PPIf?) _ _ M _ _, Control D 500 20

CNA *

(Control) 500 72

Untreated

* CNA:

NO <c &

THERE

Example 35

This example illustrates the fungicidal effect of some of the benzoxazolone derivatives used as seed buds against Cochliobulus miyabeanus.

10 g of rice seeds (of the "Asaminori" variety) infected with the disease were packed in a Saron net bag and placed in a 50 ml glass, where they were soaked at 15 ° C for 24 hours in a diluted formulation added. (composed as described in Example 34) in the same quantity? than that of rice seeds? The seeds were then removed from the formulation and immersed in deionized water at 15 ° C for a period of 5 days, after which they were germinated at 30 ° C for 24 hours. The germinated rice seeds were sown on the soil of black volcanic ash (in coporants 9 * 5 g of ammonium sulphate, 6 g of calcium superphosphate and 1.5 g of potassium chloride) in baskets for plants (30 x 60 x 10 cm). The baskets were then kept in a greenhouse at 24? C to allow for growth?

20 days after sowing, in correspondence with the stage of the third foliage, visual checks were made of the extent of the attack of the disease on the seedlings in each treated area with the following gradation terms:

Gradation Measure of disease attack Negligible Disease attack observed only in very small parts of the primary leaf or in the leaf sheath?

Moderate Primary leaf nearly turned brown and killed by brown lesions on true primary and secondary leaves?

Severe Significantly poor growth of seedlings, which bent and turned brown and died?

The disease attack rate (attack rate) was determined from the total seedlings rated as "severe" and "moderate" and the seed drug rate (or seed disinfection) was calculated with the following equation:

Attack rate

Medical rate in treated areas

seed (%) = (1 - Attack rate) x 100 in untreated areas

The semen medicament rate? an average value of the results of the tests which were carried out in two replicates for each concentration of the active ingredient? Phytotoxicity? of the rice plants was visually ascertained by means of the same gradation as indicated in Example 32?

Are the results given in the Tab? 6 below.

TABLE 6

Compound Concentration Rate medicarti. Pitotoxicity No? (ppm) _. seed (?) _

1 500 98

3 500 97 0

10 500 96 0

11 500 98 0

M 500 92 0

Control A 500 63 2

n B 500 72 3

? i C 500 40 1

"D 500 40 1

TMTD *

(Control) 2000 70

Untreated 0

II II

* TMTD: (CH3) 2NC - S - S - CN (CH3) 2

Example 36

Were the benzoxazolone derivatives tested for their activity? of seed dressing against Gibberella fujikuroi.

The test procedure used was the same as that described in Example 35 * except that rice seeds (of the "Reimei" variety) were used /

naturally infected by the disease and that the visual checks were made 26 days after sowing (at the stage of the fourth foliage). Are the results shown in Tab. 7?

TABLE 7

Compound Concentration Rate medicam. Phytotoxicity? No. (ppm) .Bernes .... (%) _

1 500 98 1

3 500 100 0

10 500 98 0

11 500 96 1

14 500 88 0

17 500 90 0

18 500 88 0

19 500 92 0

Control A 500 47 0

? B 500 52 3 Compound Concentration Rate medicam. Phytotoxicity? No, _ (ppm) _ seed (%),

Benomyl *

(Control) 500 98 0

Untreated 0

* Benomyl: N V NHCOOCH;

No.

CONHCi ^ Hg-n

Example 37

In this example, were the benzoxazolone derivatives tested against Phytophthora infestans? Were dilute suspensions of a wettable powder containing the required concentrations of the active ingredient prepared as described in Example 34? The test suspension was applied at a rate of 10 ml per pot on young tomato seedlings (of the "Sekaiichi" variety) at the third true leaf stage, which had been grown in soil in 9 cm diameter biscuit pots. in a greenhouse? Spores of Phytophthora infestans that had been produced on potato tubers were suspended in sterilized water to give a sporic or spore concentration in which 20-30 spores are observed in a single microscope observation with 150 magnification. .

One day after application the tomato seedlings leaves were inoculated with drops of the spore suspension and the seedlings were then kept at 20 ° C in a humid room to allow for the development of the disease. 3 days more later, the plates were removed from the room and the number of leaves attacked was counted. The percentage of leaves attacked and disease control were calculated with the following equations:

Percentage of Number of leaves attacked leaves = _ x 100 Number of leaves inoculated Percentage of leaves at-Control of taccate in treated areas disease (?)) X100

Percentage of leaves attacked in untreated areas Phytotoxicity? towards tomato plants was evaluated by means of the same gradation defined in example 32. The results were collected in the following Table 8.

Table 9

Compound '? * Concentration Disease Control Pitotoxicity No. (ppm) _ (%)

1 500 100 0

3 500 92 0

4 500 97 0

6 500 99 0

7 500 94 0

10 500 98 0

11 500 88 0

13 500 99 0

14 500 99 0

15 500 96 0

18 500 97 0

19 500 99 0

20 500 98 0

21 500 96 0

24 500 97 0

30 500 94 0

31 500 98 0

33 500 94 0

36 500 99 0

37 500 100 0

38 500 100 0

41 500 100 0

42 500 98 0

47 500 96 0 Compound Concentration Disease control Phytotoxicity.

No. (PPm) (*) _

50 500 100 0 o

51 500 98 0

56 500 98 0

? = 3

59 500 98 0

60 500 98 0

61 500 90 0

62 500 100 0

67 500 92 0

68 500 98 0

Control, A 500 0 0

? B 500 0 0

"C 500 0 0

"D 500 0 0

Maneb *

(Control.) 500 87

Don't treat it

* Maneb:

CH2HNCS

I ^> Mn

CH2HNCS

s

Example 38

This example illustrates the activity? of derivatives against Sphaerotheca fulginea.

The diluted formulation prepared as in example 37 was applied at a rate of 10 ml per pot on cucumber seedlings ("Sagamihanjiro" variety) at the first leaf stage, which had been grown in soil in 9 cm biscuit pots. in diameter in a greenhouse. The next day the seedlings were spray inoculated with a spore suspension of Sphaerotheca fulginea. Ten days after inoculation, assessments were made of the percentage of the damaged surface on the seedlings and disease control was calculated with the following equation:

Percentage of the Zionata le-Control area in disease treated areas (%) = (1 -) x100

Percentage of the injured area born in untreated areas

The results were tabulated in Table 9 below.

TABLE 9

Compound Concentration Disease Control Phytotoxicity? No. (ppm) _ _

1 200 92

4 200 95 0

5 200 92 0

8 200 90 0

9 200 90 0

10 200 96 0

11 200 92 0 Compound Concentration Disease Control FitotnssioitA No. (PPm)

18 200 90 0

19 200 98 0

22 200 82 0

29 200 85 0

33 200 92 0

36 200 96 0

40 200 94 0

45 200 100! 0

47 200 98 0

52 200 100 0

55 200 100 0

58 200 100 0

59 200 100 0

60 200 100 0

61 200 100 0

63 200 97 0

64 200 100 0

65 200 99 0

66 200 100 0

69 200 100 0

70 200 100 0

Controller 200 20 1

"B 200 10 1

"C 200 10 1

EN D 200 13 1 Control Concentration Disease Control Phytotoxicity? No . (ppm) _ _ _ _ _ _

Dimethirimol *

(Control) 200 95

Untreated

? Dimethirimol: n-C4H,

CH,

I? N (CH, 3) a

Example 39

The benzoxazolone derivatives were tested with Pseudoperonospora cubensis.

The diluted formulation, prepared as in Example 37, was applied at a rate of 10 ml per pot to the rear faces of the leaves of young cucumber seedlings ("Sagamihanjiro" variety) at the first true leaf stage, which had been grown in soil within 9 cm diameter cookie pots in a greenhouse. Spores of Pseudoperonospora cubensis, which had been produced on cucumber leaves in a disease developing environment, were brushed off in deionized water containing 50 ppm d? Tween 20 (trade name of polyoxyethylene sorbitan monolaurate, produced by Kao Atlas Co.) in order to give an inoculum having a concentration of spores whereby 20-30 spores were identifiable with a microscope observation at 150 magnification. One day after application, the leaves of the cucumber seedlings were spray inoculated on their lower surface treated with the inoculum. After the completion of the inoculation, the seedlings were first placed in a humid room at 20 ° C and then kept in a greenhouse at 24 ° C to allow the development of the disease. Six days more? later, the seedlings were removed from the greenhouse and the percentage of the damaged area per pot was evaluated. Disease control (??) was calculated by means of the equation indicated in Example 38 and phytotoxicity was evaluated. of the cucumber plants by means of the same gradation as in Example 32.

The results were indicated in Table 10 below.

TABLE 10

Compound Concentration but

No. . .. _Control m _ disease Phytotoxicity?

1 500 100 0

3 500 98 0

7 500 90 0

10 500 100 0

11 500 95 0

13 500 100 0

14 500 100 0

18 500 100 0

19 500 100 0

20 500 88 0

21 500 96 0

Compound Concentration Control, PitotosBicit Disease? No . (PPm) (?)

23 500 99 0

31 500 98 0

33 500 100 0

37 500 100 0

44 500 92 0

45 500 98 0

46 500 100 0

47 500 94 0

50? 500 100 0

51 500 100 0

52 500 98 0

53 500 100 0

55 500 96 0

60 500 96 0

61 500 100 0

62 500 100 0

63 500 100 0

68 500 99 0

69 500 100 0

70 500 100 0

Control A 500 20 1

"B 500 25 1

"C 500 30 1

500 36 1 Maneb

(ContraL) 500 90

Untreated 0

Example 40

The benzoxazolone derivatives were tested with Collectotrichum lagenarjum (anthracnose on cucumber).

The diluted formulation, prepared as in Example 37, was applied at a rate of 10 ml per pot to the leaves of the young cucumber seedlings (various "Sagamihanpaku" teas) at the stage of the first true leaf, which had been grown in soil in pots. of biscuit of 9 ci of diameter ih a greenhouse. The spores of Collectotrichum lagenarjum produced by incubation on an agar medium and had flour at 24 ° C for 10 days were suspended in sterilized water containing 50 ppm of Tween 20, to give a suspension of a concentration of spore, in the which about 100 spores were identified in a microscope observation with 150 magnification. One day after application, the treated leaves of the cucumber seedlings were inoculated with the aforementioned spore suspension. The seedlings cos? inoculated were subsequently treated in the same manner as indicated in Example 39, and disease control was calculated by means of the following equation:

????????? and in areas dealt with

disease (%) = 0) x 100

Number of lesions in untreated areas

The results are shown in Tab. 11, following Tab. 11

Control Concentration Disease Control Phytotoxicity? No . (ppm) _ (%) _

1 500 100 0

3 500 98 0

7 500 96 0

10 500 100 0

19 500 100 0

21 500 88 0

23 500 97 0

28 500 94 0

31 500 98 0

33 500 100 0

36 500 100 0

37 500 100 0

40 500 98 0

44 500 96 0

46 500 100 0

49 500 99 0

50 500 100 0

54 500 98 0

55 500 100 0

58 500 100 0

60 500 94 0

62 500 100 0

69 500 100 0

70 500 100 0

Compound Concentration Disease Control Phytotoxicity? No. _ (ppm) m _

Control A 500 45 1 *? B 500 37 1 "C 500 35 1? D 500 43 1 TPN *

(Control) 500 98 0

Untreated - 0

* TPN: CI

No.

1

CN

Example 41

This example illustrates the activity? of benzoxazolone derivatives against Puccinja recondita (wheat leaf rust).

The diluted formulation, prepared as in Example 37, was applied at a rate of 20 ml every three pots to young wheat seedlings (variety "Norin No. 61?) At the first true leaf stage, which had been grown in soil within 9 cm diameter biscuit pots in a greenhouse. Spores of uredosurus of Puccinia recondita, which had been produced on wheat leaves, were removed with a brush in sterilized water containing 50 ppm of Tween 20, in order to give a inoculation of a spore suspension having a sporic concentration in which approximately 50 spores were observed under a microscope observation of 150 magnification. One day after application, the wheat seedlings were spray inoculated with the inoculum. completion of the inoculation, the seedlings were first kept overnight in a humid room at 20 ° C and then transferred to a greenhouse at 20 ° C to allow disease to develop. Ten days after inoculation, it was contat o the number of uredosori fungi that the disease had developed for each leaf and the disease control was calculated by means of the equation:

Control of the number of uredosors in disease (%)? (1 treated areas) x 100

Number of uredosors in

untreated areas

Phytotoxicity? of wheat plants was evaluated by means of the same gradation defined in example 32. The results were given in Table 12 below.

TABLE 12

Compound Concentration Disease Control Phytotoxicity No. _ (ppm) _ &! _

1 200 100 0

3 200 92 0

8 200 90 0

10 200 100 0

19 200 98 0 Control A 200 10 1

"B 200 5/0

? C 200 10 1

"D 200 5 0 Maneb

(Control) 200 96 0 Untreated - 0

Example 42

Some of the benzoxazolone derivatives were tested against Pellicularia Sasaki.

The diluted formulation, prepared as in example 37? was applied in the measure of 40 mi by three goes yes to the rice seedlings at the stage of the sixth leaf me? which had been grown in soil in 9 cm diameter cookie pots in a greenhouse. The following day the seedlings with fungal disease were inoculated, placing an agar disc on the second sheath of the leaf obtained by piercing the edge of the colony of Pellicularia Sasalci mushrooms that had been incubated with a cork bur having a diameter of 5 mm. on a medium papaya sucrose agar at 27 ° C for 48 hours? Were the inoculated seedlings then kept overnight in a humid chamber? Within days after infection, evaluations of the length of the lesions were made and disease control was calculated by means of the following equation:

Length of the le-Control of the

sions in treated areas * disease (%) = (1 x 100

Length of lesions' in untreated areas

The test results are indicated in Tab, 13 below

TABLE 13

Compound No. Concentration (ppm) Disease Control (%)

69 500 100

70 500 90

Control A 500 15

'? B 500 0

"C 500 10

'? D 500 0

Validamycin

(Control) 125 90

Untreated 0

Example 43

In this example the benzoxazolone derivatives were tested against fungi and bacteria capable of deteriorating industrial materials.

The tests were conducted following the agar dilution method as described in Example 31, but the incubation was carried out for 3 days at 28 ° C for fungi and 30 ° C for bacteria. The tests were carried out in two replicates for each concentration of the active compound under test and an average range of minimum inhibitory concentrations (MIC) was determined. The results are shown in the following Table 14.

Tab, 14

Compound 'MIC No. (yg / ml)

test organisms

1 2 3 4 5 6 7 8 Escherichia coli <1.25 <5 <1.25 <1.25 <2.5 <1.25 <5 <5

Bacillus subtilis <1.25 <5 <1.25 <2.5 <5 <1.25 <5 <5

Alcaligenes viscoluktis <1.25 <5 <1.25 <1.25 <2.5 <1.25 <5 <5

Pseudomonas aeruginosa <1.25 <10 <5 <5 <5 <5 <5 <10

Aspergillus niger <1.25 <10 <1.25 <2.5 <2.5 <2.5 <5 <10

Penicillium citrinum <1.25 <5 <1.25 <2.5 <2.5 <1.25 <5 <5

Rhizopus nigricans <1.25 <10 <2.5 <2.5 <5 <2.5 <10 <10

Cladosporium herbarum <1.25 <5 <1.25 <1.25 <2.5 <1.25 <5 <5

Chaetomium globosum <1.25 <5 <1.25 <1.25 <1.25 <1.25 <10 <10 Compound No. MIC (yg / ml)

test myeroorganisms 9 10 11 12 13 14 15 Escherichia coli <5 <1.25 <1.25 <2.5 <5 <5 <1.25

Bacillus subtilis <5 <1.25 <2.5 <5 <5 <2.5

Alcaligenes viscoluktis <5 <1.25 <1.25 <1.25 <2.5 <5 <2.5

Pseudomonas aeruginosa <10 <2.5 <2.5 <2.5 <5 <10

Aspergillus niger <5 <1.25 <1.25 <2.5 <5 <10 <5 Penicillium citrlnum <5 <1.25 <1.25 <2.5 <5 <10 <2.5

Rhizopus nigricans <10 <2.5 <1.25 <2.5 "<5 <5 <2.5

Cladosporium herbarum <10 <1.25 <1.25 <2.5 <10 <10 <2.5

Chaetomium globosum <10 <2.5 <?? 2.5 <5 <10 <10 <5 Compound MIC No. (yg / ml)

Jf? Ero test organisms 16 17 18 19 A B. Proxel * Escherichia coli <5 <1.25 <5 <1.25 <40 <20 <10 Bacillus subtilis <5 <1.25 <1.25 <1.25 <-40 <40 <10 Alcaligenes viscoluktis <5 <5 <5 <1.25 <40 <20 < 10 Pseuiomonas aeruginosa <5 <5 <5 <5 <80 <20 Aspergillus niger <10 <1.25 <2.5 <1.25 <80 <20 Penicilliura citrinum <5 <1.25 <2.5 <1.25 <40 <10 Rhlzopus nigricans <5 <5 < 5 <5 - <160 <80 <20 Cladosporium herbarum <5 <1.25 <2.5 <1.2-5 <80 <10 Chaetomium globosum <5 <5 <5 <2.5 <40 <20 #Proxel:

NH

1-?

f-1O

???

t-OOO Example 44

This example illustrates the growth resistance of fungi in paints containing benzoxazolone derivatives.

The tests were carried out according to the method of JIS Z-2911 as follows. A given amount of oily formulation, prepared as in Example 25, was added to a white paint based on polyvinyl acetate emulsion, and the resulting mixture was stirred for 30 seconds in a homogenizer to prepare a paint formulation, in the which was dipped a paper filter (Toyo No. 2 paper filter 12 cm in diameter. The paper was then removed from the paint formulation and dried in air, when the amount of paint deposited on the paper was adjusted to give a dry paint load of 99-100% based on the weight of the paper filter. The dried paper was cut in a 3 CJH diameter circle to form a circular sample, which was placed in the center of an agar plate medium in a Both the medium and the tube were spray inoculated with 1 ml each of the mixed sporic suspension, produced by mixing together equal amounts of the respective sporic suspensions of the three fungi (Aspergillus niger, Penic illium lutenum and Trichoderma T-1) which had been incubated separately on potato dextrose agar medium.

Subsequently, the petri dish was covered and kept in an incubator at 28 ° C for one week, to allow the incubation of the fungi, after which the growth of the fungi on the sample with the gradation of 3, 2 or 1 was ascertained. in which: 3 indicates no mycelial growth on the sample surface, 2 indicates that the mycelial growth area on the pr? peak or sample does not exceed a third of the surface of the sample, and 1 indicates that the growth area of the mycelia? greater than one third of the sample surface, as in Table 15.

TABLE 15

Compound Proportion Compound / Content Gradation returned-No. Solid paint (%) _ Mushroom resistance

1 0.15 3

3 0.15 3

10 0.15 3

11 0.15 3

15? 0.15 3

Control A 0.15 2

0.15 2

Proxel

(Control) 0.15 2

TBTO *

(Control) 0.15 2

Untreated 1

* TBTO (Used in emulsion form)

(n-C4H9) 3SnO

Example 45

This example illustrates the sludge control effect of benzoxazolone derivatives.

A certain amount? of ordinary water that is? from a paper mill, was placed in a flask into which a solution of the test compound was added to give a concentration of 10 ppm of the active ingredient in ordinary water. Before the addition of the formulation and after Q, 5, 1, 2, 4 and 8 hours from the addition of the formulation, the bacterial colony count in ordinary water was carried out by the agar dilution plate method as follows. An ordinary water sample was diluted with sterilized saline and 1 ml of the diluted solution was placed in a Petri dish. An agar broth was poured into and mixed with the diluted solution. After incubation in the plate at 30 ° C for 2 days the bacterial colony was counted by means of a colony counter, and the bacterial value per ml of ordinary water was calculated, taking into account the dilution factor with the sterilized saline solution.

The tests were conducted in two replicates and an average bacterial count was determined. The results are given in the following Table 16.

TABLE 16

Bacteria per ml of water

Interval between Compound Addition and Evaluation (Hr)

Composed

No Before

Addition

1 5,1x10 3,8x10 6, 2x10 8,1x10 6,5x10 5,7x10 3 5,1x10 4,0x10 6,8x10 8,0x10 7,4x10 6,3x10 10 5,1x107 4,1x1 O2 7,2x102 9 , 6x102 8.8x1Q2 7.5x102

(Control) 5.1x107 4.3x103 1.2x104 3.2x104 1.2x105 4.8x106 Proxel **

(Control) 5.1x10 5.1x10 9.1x10 3.1x10 7.1x10 9.0x10

* MBT Methylenebistiocyanate

** Proxel: 1,2-Benzisothiazolin-3-one

Example 46

Does this example illustrate the effectiveness of benzoxazolone derivatives as wood preservatives?

A trunk of Cryptmerica japonica (Japanese "Sugi") with a diameter of about 15 cm and length 60, which had been dried to its fiber saturation point, was sealed at both of its cross sections with an epoxy resin comprising glass wool . An oily formulation prepared as in example 25 was diluted with water at 2% concentration of the active ingredient, and then injected at a pressure of 15 kg / cm into the wood for 2 hours. Do some of that? the wood was dried in air to reduce its water content to that of humidity. spherical atmo. 2 x 2 x 1 cm sized samples were taken from dried wood and a log of the same species treated with known wood preservatives as controls, and all samples were air dried for two weeks.

These samples were then exposed to atmospheric conditions using an ultraviolet carbon arc simulator or atmospheric conditions measured for a period of two months (corresponding to six years under natural environmental conditions); then the samples were washed at a speed? of 2 00-100 mrn / min at a hydraulic pressure of 1.0 Kg / cm after irradiation with ultraviolet rays for 2 hours, and these operations were repeated in succession during said period. The samples were dried at a temperature of 60-2 ° C for 48 hours and weighed (the dry weight is indicated by W ^).

Subsequently the samples were subjected to the preservation test according to the JIS A 9302 method. In this test the samples were inoculated with Coriolellus palustris or Coriolus versicolor which had been grown at 26 ° C for 15 days on a sandy medium containing 4% glucose. , 0.3% of peptone and lt5? Of mortar extract. After incubation at 26 ° C for 90 days, mycelia and other deposits were removed from the samples which were then air dried for 24 hours, further dried at 60 ° C for 48 hours and weighed (dry weight? Denoted by W2 ), The weight loss of the samples? calculated

by means of the equation:

Weight loss (%) = W1 ~ W2 x 100

The Preservation Effectiveness (P.E.)? evaluated by means of the following equation:

Average weight loss in treated areas P * E. = (1 - for (j ^ ta average weight in untreated areas x The test results are given in Table 17 below.

TABLE 17

Compound No? P.E value,

1 100

3 98

10 96

TBTO * 40

PCP-Na ** 63

Creosote Oil 95

* Tributyltin oxide

** Sodium pentachiorophenolate

Example 47

This example illustrates the synergistic effect achieved by mixing a certain

with other known fungicides.

Wettable powder formulations containing compound No, 10 and other fungicides which were prepared as described in Example 30, were diluted with water to the required concentrations of the active ingredients. Using the diluted formulations, tests were carried out against Pseudoperonospora cubensis (cucumber), Sphaerotheca fuiiginea (cucumber) and Sclerotinia sclerotiorum (French beans) with the procedures indicated, respectively, in examples 39, 38 and 34 above.

In order to have references, further tests were conducted in the same way, using similar diluted formulations containing the compound No, 10 alone or other fungicides alone.

Speed of application and disease control of compound No, 10 alone (A) were 25 ppm and 26% for Pseudoperonospora cubensis, 50 ppm and 24% for Sphaerotheca fuliginea and 50 ppm and 26% for Sclerotinia sclerotiorum.

The results of the tests with other known fungicides alone (B) and mixed fungicides (A B) are summarized in Tables 18, 19 and 20 below.

Table 18

Activities against Pssudoperonospora cubensie

single fungicide (B) Fungicides in mixture

Chemical Concentration Control Concentration Control (PPa) disease (#) A B disease (#)

H-Trichloromethylts o-4- 25 28 25 25 78 cyclohexene-1 f2-dicarboxy

me de

Tetradoroisophthalonitrile 25 35 25 25 86

Ethylenehi s (ditiooarbamm? T?)

manganese 25. 38 25 25 87

Manganese zinc complex

ethyl en and b? s (of t i ocarbammat o) 25 32 25 25 84

Dizinc bis (dimethyldithiocarbamate) ethyl enebis (diti ocarbammat o) 25 33 25 25 83

Basic copper chloride 50 (as Cu) 29 25 50 85

Basic copper sulphate 50 (as Cu) 24 25 50 81

Bame 8-hydroxyquinollnate 50 28 25 50 78

tethyl DL-N- (2,6-dimethylphenyl) -N- (2 1-methoxyacetyl) alanylate 5 38 25+ 5 87

Ethyl H- (3-dimethylamino-propyl)

thiocarbammat or hydrochloride 10 30 25 10 80

Table 19

Activities against Sphaerotheca fuliginea

Single fungicide (B) Fungicide in mixture

Chemical Conc entaction Control Concentration Control (h-pn) disease A B disease (#) 1, 2-Bis (3-methoxycarbonyl-2-32

thioureido) benzene 50 5 80 Methyl 1- (n-butylcarbamoyl) -2-benzimidazolecarbamate 34 50 5 83

1- [2- (2, 4-Dichlorophenyl) -4- 1 40 50 1 88 ethyl-1 f3-oxorane-2-yl) methylJ

-1H-1, 2,4-triazolepiomycin 10 32 50 10 87

4-01orof en oxy-3, 3-dimethyl-1 ~ (1 E- 1, 3, 4- tri az ol- 1 -yl) 2- 1 34 50 1 81 butanone

5-a-Buti 1- S 1 -p-t-butylbenzyl-N-3-pyridyldite ocarboxymidate 1 40. 50 1 87

N-Propyl-N- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1- 5 27 50 5 78 carboxamide

2-Dioethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine 5 26 50 5 74

6-? Ethylguinoxalin (? - 2 f 3-5 28 50 5 84 dithiocarbonate

Table 20

Activities against Sclerotinia sclerotirum

S? Ngolo fungicide (B) Fungicides in mixture

Control Concentration Control Chemical Product Concentration

(ppm) disease (%) A B disease (?)

N <,> - Dichlorofluoromethylthio-K, K-50 26 50 50 77 dimethyl-N * -f enyl sulf ami d e

2,6-Dichlor? -4? nitroaniline 50 26 50 50 79

N- (3, 5-Di chl or of enyl) -1, 2-dimethylcyclopropane-1, 2- 12.5 40 50 12, 5 89 dicarboxymide

3- (3, 5-Dichlorophenyl) -5-ethenyl-5-methyl-2, 4-oxaz olidine-dione 12, 5 36 50 12.5 85

1-Isopropylcarbamoyl-3- (3, 5-dichlorofenyl) hidantoin 12, 5 38 50 12, 5 87 Polyoxin 25 32 .. 50 25 82

N-tetrachlorOethylthio-4-cycle-25 36 50 25 85 hexene-1,2-dicarboxymide

1? ? ?

Claims (10)

1) A compound of benzoxazolone of the general formula: ?? i CO 0 N>? Yn (I) R. wherein: X represents a lower alkyl group; Y represents a halogen atom; m? 0 or an integer from to 3; n? an integer from 1 to 3; and the sum of m n? an integer from 2 to 4? even though ch? when m? 0, n both 3J and Yn stands for the group 5,6,7-trichloro; and R represents a hydrogen atom or an alkyl, alkylcarbonyl, haloalkyl carbonyl, alkyloxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, mono- or di-alkylamino carbonyl, alkylsulfonyl, phenylsulfonyl or optionally substituted benzoyl or phenylamenocarbonyl groups. 2) A compound according to claim 1, in which in? 0 and Yn? the 5,6,7-trichloro group. 3) A compound according to claim 1, in which m? 1, X? methyl, n? 2 and each Y? chlorine. 4) A compound according to claim 3? in which Xm? 7-methyl and Yn? 5t6-dichloro. 5) A compound according to claim 1, in which m? zero, Yn? the 5,6,7-trichloro group and R? an alkenylcarbonyl or alkenyloxycarbonyl group. 6) A compound according to claim 1, which ? chosen from the following: 5, 6,7-trichlorobenzoxazolone, N-acetyl-5, 6,7-trichlorobenzoxazolone, N-methoxycarbonyl-5, 6,7-trichlorobenzoxazolone, N? (3,5? Dicorophenylcarbamoyl) 5 * 7? Trichlorobenzoxazolon N-methanosulfonyl-5,6,7-trichlorobenzoxazolone, N-isopropoxycarbonyl-5, 6,7-trichlorobenzoxazolone, 5, 6-dichloro-7-methylbenzoxazolone, N-acetyl-5, 6-dichloro-7-nethylbenzoxazolone, N-methoxycarbonyl-5, 6-dichloro-7-methylbenzoxazolone and N-allyloxycarbonyl-5, 6,7-trichlorobenzoxazolone. 7) A bactericidal and fungicidal composition for non-medical use, comprising as an active ingredient a compound having a defined general formula (i) in claim 1, in association with a vehicle the or diluent for the active ingredient * 8) A composition according to claim 5? in the form of a concentrate comprising 10 to 95% by weight of the active ingredient * 9) A composition according to the claim 5, in the form of a dilute formulation comprising 5 te from 1x10 to 10% by weight of the active ingredient. 10) A method to control the growth of fungi and bacteria in a plant or industrial material, which method comprises the application of a compound of general formula (i) such as? defined in claim (1) to the plant or industrial material or plant location which? infesta ta or pu? be infested with fungi and bacteria? 11) A process for preparing a compound of general formula (1) according to claim 1, which comprises: (a) reacting a compound of the formula: Xm OH (The) Yn NHR wherein X, Y, mf n and R are as defined in claim 1, with a carbonyl compound of the formula 0 = di!) wherein A and B, which may be the same or different, each represent a halogen atom or an alkoxy, haloalkoxy, alkylthio or animine group; (b) the halogenation of a compound of the formula: Xm C = 0 (IV) wherein X, m and R are as defined in claim?, z represents a halogen atom and p? 0, 1 or 2, to produce a compound of formula (I) bearing in the benzene ring a halogen or halogens, the number of which? a unit? in more? than that of halogen or halogens in the starting compound of formula (IV); (c) reacting, in the presence of an acid ligand, a compound of the formula: C = 0 (VI) wherein X, Y, m and n are as defined in claim 1, with a compound of the formula: RD (VII) in which R? as defined in claim 1 except that for the hydrogen atom and D represents a halogen atom, or with a di-alkyl sulfate of the formula R0 p so2 R0 where R? an alkyl group, to produce a compound of the formula (I) wherein R? different from the hydrogen atom; or (d) reacting a compound of the above formula (VI) with an isocyanate compound of the formula: R * NCO (VIII) wherein R * represents an alkyl group or optionally substituted phenyl to produce a compound of the formula (i) where R? a group of -CONHR '? DESCRIPTION 1. Title of the Invention: Derivatives of benzoxazolone 2, Claims: 1. A derivative of benzoxazolone of the general formula ?? 1? ? .1.? ? * -J -a 0 K '.T-? * I: i-s .;. 3fhr. <!? t? t, ViS i. wherein X represents a lower alkyl group; Y ra? has a halogen atom; m and n are each an integer, 1 or pi? and the sum m n? 2 to 4; and R represents a hydrogen atom or an optionally substituted alkyl, alkylcarbonyl, haloalkylcarbonyl, alkyloxycarbonyl, mono- or di-alkylaminocarbonyl, alkylsulfonyl, phenylsulfonyl or benzoyl or phenylaminocarbonyl group. 2. A microbicidal composition for use in agriculture and horticulture which includes as an active ingredient a derivative of benzoxazolone del. the general formula: * f * ?. v * ? Yri in which X represents a lower alkyl group; Y represents a halogen atom; m and n each represent an integer, 1 or pi ?, and the sum m n eda 2a 4; eR represents a hydrogeon atom or an alkyl, alkylcarbonyl, haloalkylcarbonyl, alkyloxycarbonyl, mono- or di-alkylaminocarbonyl, alkylsulfonyl, phenylsulfonyl group or an optionally substituted benzoyl or phenylaminocarbonyl group. 3. Detailed description of the invention This invention relates to new derivatives of benzoxazolone and their uses as a microbicide in agriculture or horticulture. Pi? in particular, this invention relates to derivatives of benzoxazolone of the general formula (I): m V. / - 0 CD w R. wherein X represents a lower alkyl group; Y represents a halogen atom; m and n are each an integer, 1 or pi ?, and the sum m n? 2 to 4; B represents a hydrogen atom or an alkyl, alkylcarbonyl, haloalkylcarbonyl, alkylasycarbonyl, mono- or di-alkylaminocarbonyl, alkylsulfonyl, phenylsulfonyl group or an optionally substituted benzoyl or phenylaminocarbonyl group, and also microbicidal compositions for use in agriculture and in horticulture which include them as an active ingredient. Has a variety been synthesized? of benzoxazolone derivatives and? has been carefully evaluated the uta lit? commercialization of them in order to develop new myorobics of which have low toxicity, good safety and wide applications. As a result, yes? ascertained that the new derivatives of benzoxazolone of the above general formula (I) possess excellent properties? as fungicides and bactericides for impi? go in agriculture and horticulture. These compounds have a high activity? against various fungi and bacteria and are widely used as microbicides in agriculture and horticulture. So, for example, the compounds of this invention can control the Piricularia oryzae (rice blight), it Cochliob? Lus miyabeanua (elminthosporiosis or rice neck pain) and the Xanthomonas oryzae ("bacterial leaf blight") of rice when are applied to aquatic rice. If the compounds are used in fruit growing and horticulture, they can effectively control the Alternarla kikuchiana ("black spot") of the pear, the G-lomerella cingulata ("ripe rot") of the vine, the Cladqsporium fulvum ("leaf mold") of the tomato, Phytophthpra infestans ("late blight") of tomato, Sclerptinia sclerotiorum ("stem rot") of green bean, Spherotheca fuliginea ("powdery mildew") of cucumber, Fusarium oxysporum ("fusarium wilt") of cucumber, the Pseudpperonospora cubensis (downy mildew) of the cucumber; the Colietotrichum lagenarium (anthracnose) of the cucumber.! 'Erwinia aroidea ("soft rot") of the Chinese cabbage. Some of the compounds are very effective as seed fertilizers, for example against Gibberella fu.iikuroi (white rice mold) and Cochliobolus miyabeanus (helminthosporiosis or rice neck pain). The compounds of the invention have a strong microbicidal action, while they are not toxic to useful plants, humans and animals including fish, and therefore can be used without danger as microbicides of great value. ? compounds of this invention can be prepared with the reaction methods set out in schemes (a)? (b) and (c) as reported below, and some compounds can be obtained with the method shown in diagram (d) described below: Scheme (a) Xm ? _ v "OH ? r - A = c ^ 0 w> OSn? Yn / ??? ? (III) In general formula (II), the symbols R, X, Y, m and n have the same meanings as those given above. The compounds of formula (II) in which R?, For example, an acetyl group can be prepared with a high yield by acetylating, in the traditional way, the appropriate ortho-aminophenol at the kyl-substituted? less hours to obtain a lower 2-acetoaminophenol alkyl - substituted and therefore halogenating the latter THE with a required equivalent of halogen. The compound cc> s? got pu? be hydrolyzed, for example, with dilute hydrochloric acid to obtain the corresponding compound of formula (II), wherein R? a hydrogen atom. Poioh? the last compound of R? hydrogen it can? be ^ acylated by any traditional method to provide a variety? of compound (II). In the general formula (III), the symbols A and B which may be the same or different each represent a halogen, alkoxy, haloalkoxy, alkylthio or animine group. The compounds of formula (III) include phosgenic compounds such as phosgene and diphosgene (ie trichloro methyl chloroformate), haloformates, halothiolformates, carbonic diesters and urea. According to scheme (a), it is generally believed that compound (I) can be produced in two steps, in which compound HA or HB? eliminated with the reaction between compound (II) and compound (III) to form an intermediate product thereof, which is then reacted with compound (III) to allow further elimination of compound HB or HA, respectively. Hence, if a stable intermediate product is formed which depends on the nature of the compounds (III) used, it can? first be isolated and then cyclized to produce the final compound (I). Such a stable intermediate product can? be formed with an alternative method without resorting to the reaction between compound (II) and compound (III) and then cyclized to obtain compound (I). L? reaction between compounds (II) and (III) according to the sch? but (a) pu? be carried out in the absence of solvent, but preferably in the presence of an organic solvent that can? also be an excess of component (II) itself. Examples of the usable solvent include hydrocarbons, halogenated hydrocarbons, ethers, esters, acid starches, alcohols and dimethylsulfoxide, among which will be selected. for use a suitable solvent according to the nature of the compound (III). To make the reaction progress in a regular way, it can? be used as an acid binding agent, however some compounds (III) can lead to the formation of an acid during the course of the reaction. The acid binding agent to be used for this purpose includes organic amplines such as triethyl apimin and pyridine and inorganic bases such as potassium carbonate. The reaction can? be carried out at room temperature, although it can be completed in a longer period of time? short if carried out at high temperature. At the end of the reaction, said comp_q sto pu? be isolated, for example, by filtering the salt or the sal? of the acid binding agent precipitated in the reaction mixture in which? used the binder, and then evaporating the solvent from the filtrate. Alternatively, a suitable solvent such as benzene, chloroform, ether or tetrahydrofuran and water can be used. be added to the reaction mixture to fractionally precipitate from. it the compound in question. Details of the method according to scheme (a) are reported below in Examples 1-4. Scheme (b) 0 (0 halogen agent) <ZP>! R Y A (??) Cv) co In the general formula (IV), R, X and Y are as defined above, Z? a halogen atom and P? 0, 1 or 2. The compounds of the formula (IV) can be obtained according to the method illustrated above for scheme (a). Examples of the halogenating agent to be used include halogens such as chlorine or bromine and sulfuryl chloride alone and combinations of d? a hydrohalogenic acid and an oxidizing agent such as lime chloride, potassium chlorate or d? manganese. In scheme (b), the halogenation reaction is generally carried out in a solvent and at a high temperature to accelerate the reaction in case the halogenation is carried out with a halogen such as chlorine or bromine or with sulfuryl chloride. The solvent that can? be used in this case includes a, water, acetic acid and halogenated hydrocarbons. If halogenation? conducted using in combination an acid such as hydrochloric acid or hydrobromic acid and an oxidizing agent such as chloride of lime, potassium chlorate or manganese dioxide, then the compound (IV) can? being dissolved in the acid with subsequent addition of the powder of the oxidizing agent or a concentrated aqueous solution thereof. If necessary, can it? a solvent such as acetic acid be employed. The presence of a catalyst, for example iron, iron chloride, a phosphorus compound, aluminum chloride, antimony chloride or ultraviolet radiation serves to progress regulating the reaction of scheme (b). At the end of the reaction, the compound in question (I) can? be recovered from the reaction solution directly by evaporation of the solvent or possibly by adding to the reaction solution an appropriate solvent such as benzene, chloroform, ether or tetrahydrofuran and water for the purposes of fractional extraction. Details of the method according to scheme (b) are indicated below in Examples 5-7 ?. Scheme (c Xm Xm 0 = 0 + RX (^ e <g0>? <1> ^ <6> ac <i> do) No. Yn H Yn (VI) (VII) (I) In formula (VI), X, Y, m and n have the same meanings as before. In formula (VII), R? one of the groups as defined above except hydrogen atom and stands for a halogen atom or an alkylsulfonic or arylsulfonic acid group. Therefore, the compounds of the formula (VII) include alkyl halide, acyl halides, dialkyl sulfates and arylsulfonic esters. Can these compounds be readily obtained by conventional methods per se? known. The reaction between compound (VI) and compound (VII) according to scheme (c) can? be carried out in the absence of solvent, but preferably in the presence of an organic solvent which can also be an excess of the same compound (VII). Examples of the solvent to be employed include hydrocarbons, halogenated hydrocarbons, ethers, esters, ketones, acid starches, alcohols and dimethylsulf oxide. The acid ligand to be used for the reaction comprises organic amines such as triethiamine and pyridine and inorganic bases such as potassium carbonate. The reaction can? be carried out at room temperature or suitably at a high temperature. Obviously, the time required will depend? by the nature of the compound (VII) used, by the nature of the solvent if this? used and the reaction temperature used, although it may be higher. short when the reaction takes place in a polar solvent. For the r? cup of the compound in question at the end of the reaction, the resulting reaction solution can? be filtered to remove a salt of the precipitated acid ligand, and the filtrate can be be evaporated to leave the desired mixture. In some cases, to extract the compound in question, it is possible to: add to the mixture d? reaction a suitable organic solvent such as benzene, chloroform, ether or tetrahydrofuran and water. Details of the method according to scheme (c) are reported below in Gsamples 8-10 .; Scheme (d) C = 0 R'NCO C? 0 CONHR (vi) (VIII) (IX) In formulas (VIII) and (IX), R1 stands for an alkyl group or an optionally substituted phenyl group? to. Therefore, the method illustrated in diagram (d)? usable for the preparation of the compounds of the formula (I), in which R represents an optionally substituted alkylaminocarbonyl or phenylaminocarbonyl group? The reaction between compounds (VI) and (VIII) according to scheme (d) can? be carried out in the absence of solvent, but preferably in the presence of an organic solvent that can? also be an excess of the same compound (VIII). The solvent to be used; under reaction conditions it should be inert with respect to compounds (VIII) and includes for example hydrocarbons, halogenated hydrocarbons, ethers, esters and ketones. If as a catalyst? present a small amount? of organic amine such as triethylamine or pyridine, the reaction will proceed? very smoothly. The reaction can? be conducted satisfactorily at room temperature or possibly at an elevated temperature. The duration required for the reaction will depend? from the nature of the compound (VTII) used, even if the reaction can? generally be completed in a relatively short time. At the end of the reaction, the compound in question can? be isolated from the reaction mixture by filtering the crystals of the desired compound or, as the case may be, by evaporating the solvent. The method according to scheme (d)? illustrated more? in detail with reference to Example 11. Example 1 Preparation of compound No. 6 15.8 g of 2-amino-4 ~ chloro-6-methylphenol, 27.6 g of anhydrous potassium carbonate and 150 ml of toluene were placed in a round bottom flask and 9.9 g of phosgene was slowly introduced into the mixture by mixing with cooling in an ice and water bath. The standout blend? was heated to reflux for one hour and the reaction solution? it was then cooled and transferred to a 500ml separating funnel. 150 ml of tetrahydrofaran and 150 ml of water were added to the funnel and the organic layer? 3 separated, dried over anhydrous sodium sulfate and then evaporated at reduced temperature to remove the solvent, leaving brown crystals. The crystals were recrystallized from a mixed solvent of hexane and acetone to give 15.6 g of 5-chloro-7-methylbenzoxazolone in yellowish brown crystals with a melting point of 232-234 ° C. Example 2 Preparation of compound No. 48 21.2 g of 2-amraine-3,5-dimethyl 1-4,6-dichlorophenol, 27.6 g of anhydrous potassium carbonate and 150 ml of ethyl acetate were placed in a 300 ml round bottom flask and a solution of 9.9 g diphosgene (trichloromethyl chloroformate) dissolved in 50 ml of ethyl acetate? was added dropwise to the mixture with stirring under cooling in an ice-water bath. The resulting mixture? 3 was heated at reflux temperature for one hour, and what about the reaction solution? it was then cooled to precipitate the salts, which were removed by suction filtration. The filtrate? was concentrated to dryness under reduced pressure to give yellow crystals which were crystallized from a mixed solvent of methanol / acetone to give 20.9 g of 4,6-dimethyl-5, 7-dichlorobenzoS3azolone in the form of pale yellow crystals with a melting point of 271-272 ° C. Example 3 Preparation of compound No. 1 23.0 g of 2-ethoxycarbonylamino-4-methyl-5-ci was placed in a 100 round bottom flask. rofenol (prepared from 2-amino-4-meths 1-5 -chlorophenol and ethyl chloroformate), 50 ml of dimethylphormamide and 0.5 g of anhydrous potassium carbonate and the mixture? was heated with stirring at 40 ° C for 4 hours. The resulting reaction solution? was cooled and poured into 100 ml of water to separate crystals, which were collected by suction filtration and air dried at 80 ° C for two hours to obtain yellow crystals. Recrystallization of the latter from methanol yielded 15.6 g of pale yellow 5-methyl-6-chlorobenzoxazolone crystals with a melting point of 182? -184? C. Example 4 Preparation of compound No. 33 15, 1 g d? 2-amino-4-isopropylphenol and 100 ml of acetic acid were placed in a 300 ml round bottom flask, followed by the addition of 10.2 g of acetic anhydride cooled to a? here and ice. The mixture ? was heated at 60 ° C for one hour to complete the reaction, resulting in the formation of 2-acetamino-4-isopropylfenol. 15.6 of chlorine gas was then passed into the reaction mixture at a temperature of 80-90 ° C and the resulting reaction solution? was cooled and concentrated with evaporation of the acetic acid under reduced pressure to leave 25.7 g of a brown oil of 2-acetamino-4-isopropyl-5, 6-dichlorophenol. The oil? was placed in a 300 ml round bottom flask, to which was added 150 ml of tetrahydrofuran followed by 9.6 g of sodium hydride (50%) 9.9 g of phosgene was then introduced into the mixture under cooling with water and ice and the resulting mixture? been stirred at room temperature for one hour. The reaction solution? was transferred to a 500ml separating funnel into which 150ml of benzene and 150ml of water and the organic layer were added. was separated, dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent, leaving brown crystals. The crystals were recrystallized from a mixed solvent of hexane and acetone to give 24.5 g of N-acetyl-5-isopropyl-6,7? Dichlorobenzoxazolone as crystals but? yellowish rones with a melting point of 133-135 ° C. Example 5 Preparation of compound No. 12 18.4 g of 5-chloro-7-? Ethylbenzoxazolone and 150 ml of acetic acid were placed in a 300 ml round bottom flask and the mixture was heated to 80-90 ° C, followed by the passage of 7, 8 g of gas chloride. The reaction solution? was concentrated with evaporation of acetic acid at reduced pressure to give 20.7 g of 5.6-dichloro-7-methylbizoxazolone as yellowish brown crystals. Recrystallization from a mixed solvent of methanol / ac? tone gave pink crystals of the compound with a melting point of 251-252 ° C. Example 6 Preparation of compound No. 35 18.4 g of 5-chloro-methylbenzoxazolone and 150 ml of acetic acid were placed in a 300 ml round bottom flask and the mixture? a solution of 17.6 g of bromine in 30 ml of acetic acid was added dropwise. The resulting mixture? was heated to 95 ° C and stirred at this temperature for 4 hours. So, the reaction solution? was cooled to room temperature and concentrated with evaporation of acetic acid under reduced pressure to give red-brown crystals, which were recrystallized from methanol / acetone to give 22.3 g of 5-chloro-6-bromine-7 -methylbenzoxazolone as brown crystals with a melting point of 262--264 ° C. Example 7 Preparation of compound No. 45 26, Og of N-acetyl-4-methyl-5,7-dichlorobenzoxazolone and 150 ml of chloroform were placed in a 300 ml round bottom flask, to which 16.5 g of sulfuryl chloride was then added at temperature environment. The mixture ? was heated to reflux temperature for two hours and the reaction solution was so? obtained? was evaporated under reduced pressure to leave yellowish white crystals,, The reaction from hexane / acetone gave 23.6 g white crystals of N-acetyl-4-methyl-5, 6,7-tryclo ro-benzoxazolone with a melting point of 125-127 ° C. Example 8 Preparation of compound No. 13 4.4 g of 5.6-dichloro-7-methylbenzoxazolone, 2.8 g of anhydrous potassium carbonate, 2.5 g of 1 sulfate templates and 50 ml of acetone were placed in a 100 ml round bottom flask. mi and the contents of the flask were heated under reflux for two hours. Subsequently, the reaction solution? been evaporated at reduced pressure and the residue? been ra? caught in 50 ml of water. The solution ? filtered to give brown to yellow crystals, which were re-installed from a solvent mixed with hexane and acetone to obtain 3.9 g of pale crystalline N-methyl-5, 6-dichloro-7- methylbenzoxazolnne with a melting point of 122-123? C. Example 9 Preparation of compound No. 16 4.4 g of 5.6-dichloro-7-methylbenzoxazolone, 2.8 g of benzene chloride and 50 ml of acetone were placed in a 100 ml round bottom flask, into which 2 were then added dropwise, 0 g of triethylamine with water and ice cooling and stirring. At the end of the addition, the resulting mixture? was heated under reflux for one hour to complete the reaction; the reaction solution? was cooled and filtered to remove precipitated salts. The filtrate? was evaporated to leave yellowish-white crystals, which were recrystallized from acetone to give 5.5 g of white N-benzo? -1-5, 6-dichloro-7-methylbenzoxazolone crystals with a melting point of 165- 166? C. Example 10 Preparation of compound No. 18 4.4 g of 5.6-dichloro-7-methylbenzoxazolone, 1.9 g of methyl chloroformate and 50 ml of acetone were placed in a 100 ml round bottom flask, into which 2 were then added dropwise , 0 g of triethylamine with water and ice cooling and stirring. At the end of the addition, the resulting mixture? been heated under reflux for one hour to complete the reaction one ^ after which? the reaction solution? it was allowed to cool and filtered to remove precipitated salts. The filtrate? was evaporated to leave yellowish brown crystals which were recrystallized from a mixed solvent of hexane and acetone to give 4.6 g pink crystals of N-methoxycarbonyl-5, 6 - dichloro-7-methylbenzoxazolone with a melting point of 1 35-1 38? C. , Example 11 Preparation of compound No. 22 4.4 g of 5.6-dichloro-7-methylbenzoxazolone, 3.8 g of 3.5-dichlorophenyl socyanate, 50 ml of acetone and three drops of triethylamine were placed in a 100 ml round bottom flask and the mixture ? been stirred at room temperature for one hour. The precipitate formed during the reaction? was filtered off to give 7f4 g of pink crystals which were identified as N-3,5-dichlorophenylcarbamoyl -5,6-dichloro? Typical examples of the compounds of the general formula (I) prepared with the methods described in the previous examples are reported in the following Table 1. In the examples and experiments below? the reference number of the compounds is also indicated. Table 1 Compound No. Structural formula Melting point (? C 1 O 182 - 184 There 0 2 o \ c = or 150 ~ 159 N <7> CH- 1 COCE There _ 3 Tot> = or 140 - 141 CH N There K CH ^ 3 A To _T? \ C = o 115 - 117 L/ CH. <5 (>! OOC2H5 ^ 0 OR . 254 - 257 / O \ c = o 232 - 234 N ' CH, 93 - 94 Ci r? R c = o COCILj There \ c = or 126 - 130 / C2H5 or 1 C = 0 101 - 103 C? H or I / 2 5 COCH There or ? ; C = o 106 - HO 2H5 C0CH2Ci !the 115 - 116 i! II C ~ H? ?the COOCH CH there Q c = o 251 "252 Ci O C = 0 122 - 123 / There CH CH There O c = o 16? - 169 COCH or C = 0 / 54 r 56 Ci COC.Ho-n 4 v \ c = o 165 - 166 - ^ 3> c = o 215? 215 co X2H THERE IS, \ <?> y 155 - 158 COO <0> CH- <0> ^ c = o 170 - 172 w CONHC c = or 179 - 180 / CH WITH o c = o 150 - 152 / CONH- / f n CH c = o 221 - 222 ir / n p CH, 0 o \ c = o 199 - 200 N / S02CH3 or 191 - 193 N / v i know C - = 0 248 - 250 / c z There o <0> \ c = o 133 ~ 135 CH- W COCH ^ There There 0 o <N> c = o 149 ~ 151 CH- N <7> COOCH-, 3 There o c = o 218 - 219 / o c = o 136 - 138 Ci N ' ? <CH> 3 ^ 0 or 103 - 105 / c = o CH COCH ^ ? c = or 127 ~ 130 / CH COOCH There 216 ~ 217 i-G or c = o There There o C = 0 133 - 135 / i-C-, H 3 7 COCH There o c = o 150 ~ 152 N / l-C'r3-H7 COOCH ^? O C = 0 262 - 264 No. Br Or 175 ~ 175 / c = o COCH CH OR ! C = 0 224 - 225 CH There o C = 0 158 - 159 / COCH There o c = o 256 ~ 259 i N There h CH, There I ^ or ? ? \ c = o 154 - 156 ci '?' '? r / There COCH Or? =? 254 - 256 / CH THERE THERE o c = o 155 ~ 157 n o I COCH-, o C = 0 174 - 176 / CH CI cooc? THERE o c = o 275 ~ 277 CI w or 125 ~ 127 / CH3 COCH3 T. ? There or \ C * 0 288 - 289 / There There Er O c = o 142 - 144 N / CH, C0C? O c = o 271 - 272 / the CH There o C = 0 117 - 118 B /? CH3 COCHJ For the application of the compounds of this invention as a microbicide in agriculture and horticulture, the compounds can be used as such or formulated in compositions in the form of wettable powders, liquid preparations, emulsions, fluid preparations. true po3 ^ (including DL-type powders) and dilution granules? using a liquid carrier such as water or an organic solvent, solid powder or other suitable carriers and adding, as required, adjuvants including wetting agents, spreading agents, emulsifying agents and adhesives. The liquid carrier to be used in the formulation includes water, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, esters, ketones, acid starches and dimethyl sulfoxide. The solid vehicle that can be used includes mineral powders such as clay, talc, kaolin, bentonite, diatomaceous earth, calcium carbonate and silicic acid, wood powders and powders of other organic materials. As examples of adjuvants, non-onic, harmonic, cationic and ampholytic surfactants, ligninsulfonic acid and its salts and glues such as gums, fatty salts and methyl cellulose can be mentioned. The compounds of this invention can be used mixed with insecticides, fungicides, herbicides or with plant growth regulators in order to extend the applications that said compounds can find. This invention? also illustrated but not them. mitigated by the following examples in which the parts are weight. Example 12 Emulsified formulation Urja emulsifiable formulation comprising 20 i? of the active ingredient? was obtained by uniformly mixing 20 parts of compound No. 17, 30 parts of dimethylformamide, 35 parts of xylene and 15 parts of polyoxyethylene aryalkyl ether until all ingredients were dissolved. Example; 13 Fluid formulation A flowable formulation comprising 40 # of the active ingredient? was prepared by uniformly mixing 40 parts of compound No. 13 together to a particle size of less than 10 ^ 2 parts. of laurels 1 sulphate * 2 parts of sodium alkyl Inafta lene splphonate, 1 part of hydroxypropyl cellulose and 55 parts of water. Example 14 Wettable dust Upa wet powder containing 20 # of the active ingredient? was obtained by grinding and uniformly mixing 20 parts of compound No. 29, 5 parts of polyoxyethylene alkyl aryether, 3 parts of calcium sulfate oil and 72 ipartides diatomaceous earth. example 15 Powder to be sprayed A spray powder comprising 3% of the active ingredient? was obtained by uniformly mixing and grinding 3 parts of compound No. 34, 0.5 parts of fine silica powders, 0.5 parts of calcium stearate, 50 parts of clay and 46 parts of talc. Example 16 Granules A composition in the form of granules comprising 5% of the active ingredient h was prepared by uniformly mixing and grinding 5 parts of compound No. 2, 1 part of calcium lignosulfonate, 30 parts of bentonite and 64 parts of clay and then granulating the mixture in the presence of added water, followed by drying and screening. Experiment 1 Tests on the activity? fungicide against rice mintosporiosis A wettable powder formulation prepared as described in Example 14? been diluted with water to obtain test formulations containing the required concentrations of the active ingredient. The test wording? was applied to four-leaf aquatic rice seedlings ("Asahi" variety), which were grown on soil in 9 cm diameter cookie pots in a greenhouse. One day after application, the treated seedlings were inoculated by spraying them with a suspension of Cochliobolus miyabeanus spores. 5 days after 1? Inoculation,? The number of lesions from helminthosporiosis or sore neck of rice per leaf at the four-leaf stage was evaluated and the control of the disease has been calculated by means of the equation shown below, phytotoxicity? against rice plants? was equally evaluated visually by the gradation indicated below. Control of the disease? an average value of the results of the tests which were carried out in two replicates at each concentration of the active ingredient. The results are shown in Table 2, where the control chemical? a commercially available fungicide (under the generic name of triazine) comprising 2,4-dichloro-6- (0-chloroanilino) -1,3,5-tria zina * N? Mere injury from elmintosp? Disease control = (1 - riosis in treated plots) x 100 Number of elmintosp lesions? riosis in untreated plots Gradation of the entity? of phytotoxicity? 5: severe damage, 4: significant damage, 3: moderate damage, 2: minor damage, 1: negligible damage, 0: no damage. Table 2 (Activity against rice intintosporiosis) Compound Concentration Disease control Cytotoxic t? No. _ (ppm) _ ($) 1 500 100 0 2 500 98 0 3 500 82 0 4 500 96 0 5 500 76 0 6 500 76 0 7 500 72 0 8 500 88 0 9 500 80 0 10 500 92 0 11 500 88 0 12 500 100 0 13 500 96 0 14 500 100 0 15 500 94 0 16 500 96 0 17 500 100 0 18 500 100 0 19 500 98 0 20 500 100 0 21 500 96 0 22 500 100 0 23 500 98 0 24 500 98 0 Compound Concentration Disease Control ^,. . . I have. _ _? _ FUoto you know quotes 25 500 96 0 26 500 88 0 27 500 98 0 28 500 98 0 29 500 76 0 30 500 72 0 31 500 98 0 32 500 82 0 33 500 76 0 34 500 88 0 35 500 94 0 36 500 98 0 37 500 73 0 38 500 88 0 39 500 98 0 40 500 100 0 41 500 98 0 42 500 96 0 43 500 100 0 44 500 76 o 45 500 82 0 46 500 80 0 47 500 100 0 48 500 72 0 500 100 0 Substance chi control mica 500 94 0 Untreated 0 Experiment 2 Tests on the activity? fungicide against rice brusone A wet powder formulation prepared as described in Example 14.? been diluted with water to obtain test formulations containing the required concentrations of the active ingredient. The state test formulation? applied to three-leaf aquatic rice seedlings ("Asahi" variety), which have been grown on earth in 9 cm diameter biscuit pots in a greenhouse. One day after the application, the treated seedlings were inoculated by sprinkling them with a suspension of Piricularia oryzae spores and incubating them in a humid chamber at a humidity level. relative of 95-100 $ and at a temperature of 24-25 ° C. 5 days after inoculation,? the number of brusone lesions per leaf at the three-leaf stage was evaluated and? Disease control was calculated using the equation below. Phytotoxicity? against rice plants? was similarly established visually by means of the same gradation as indicated in Experiment 1. Disease control is an average value of the test results which were conducted in two replicates at each concentration of the active ingredient. The results are shown in Table 3, where the control chemical? a fungicide available in connaer ci? (under the generic name of IPB emulsion) comprising 0, O-diisopropyl-S-benzylphosphorothiolate. Number of brusjj lesions Disease control = (1 - n-e ln * PPs treated ^ 1? Number of brusone lesions in untreated plots Table 3 (Activity against brusone of rice Compound Concentration Disease Control No? _ (Ppm) _ Phytotoxicity? _ 1 200 84 0 3 200 92 0 4 200 96 0 8 200 82 0 11 200 98 0 12 200 88 0 H 200 98 0 17 200 98 0 18 200 100 0 19 200 100 1 22 200 98 1 27 200 92 0 28 200 98 0 31 200 98 0 34 200 100 0 42 200 100 0 43 200 100 0 45 200 98 0 47 200 96 <? > 0 49 200 94 0 Substance who control mica 480 76 0 Untreated 0 Experiment 3 Tests on the activity? fungicide against peronospera (Phytophtora infestane) of the tomato Dilute formulations of a wet powder containing the required concentrations of the active ingredient were prepared as described in Example 14. trial ? was applied at a rate of 10 ml per pot on young tomato seedlings ("Sekaiichi" variety) at the stage of three true leaves, which were grown on soil in biscuit pots with a diameter of 9 cm in a greenhouse. Spores of Phytophtora infe stana which were produced on potato tubers were suspended in sterilized water to give a spore concentration / at which 20 to 30 could be observed by observation under a microscope at 150 magnification. One day after application, the tomato seedlings' leaves were inoculated with drops of the spore suspension and the seedlings were kept at 20 ° C in a humid chamber to allow disease to develop. 3 days later, the seedlings were removed from the chamber and? the number of leaves attacked was counted. Percentage of leaves attacked and disease control were calculated with the equation shown below. Phytotoxicity? towards tomato plants? it was also evaluated with the same gradation as me defined in Experiment 1. Percentage of Number of leaves attacked x 100 leaves attached Number of inoculated leaves Percentage of leaves fully attached-f Bf \ Disease control treated minds K7>) = V1 -) X Percentage of leaves ajt taccato in untreated plots Control of the disease? an average value of results of the tests carried out in two replicates each na concentration of the active ingredient * The results are shown in Table 4f in which the substance chi- mica control? a commercially available fungicide ie (with the generic name of maneb) comprising ethyl- manganese nebis (dithiocarbamate). Table 4 (Activities against tomato blight) Compound Concentration Disease Control Phytotoxic t? No. (PP <m>) - _ (*) 1 500 98 0 2 500 96 0 5 500 97 0 11 500 94 0 12 500 98 0 H 500 94 0 17 500 99 0 18 500 100 0 19 500 100 0 22 500 100 0 23 500 98 0 28 500 96 0 31 500 100 0 32 500 98 0 37 500 98 0 40 500 98 0 41 500 98 0 42 500 90 0 43 500 100 0 48 500 92 0 49 500 98 0 Chemical substance of con? 500 87 0 troll o Untreated 0 Experiment 4 Tests on activity? Cucumber blight fungicide Dilute formulations of a wettable powder containing the required concentrations of the active ingredient were prepared as described in Example 14. The test formulation? was applied at a rate of 10 ml per pot to the rear surface of cucumber seedling leaves ("Sagamihanjiro" variety) at the true leaf stage which were grown on soil in 9 cm diameter cookie pots in a greenhouse . Spores of Pseudoperonospora cubensis that were produced on cucumber leaves in a disease development zone were brushed off in deionized water containing 50 ppm of Tween 20 (polyoxyethylene sorbitan mono - laurate) to give an inoculum having a concen spore traction, at which 20 to 30 spores can be observed in one observation with a microscope at 150 magnification. One day after the application the leaves of the cucumber seedlings were inoculated in their lower treated surface by spraying them with the inoculum. At the end of the inoculation the plants were first placed in a humid chamber at 20 ° C for 24 hours and then kept in a greenhouse at 24 ° C to allow the development of the disease. Six days later, the seedlings were removed from the greenhouse and? The percentage of the lesion area per va s has been established. Control of the disease? was calculated by means of the equation indicated below and the phytotoxicity? against cucumber plants? was evaluated with the same gradation as in the Experiment 1. Control of the disease? an average value of the results of the tests carried out in two replicates at each concentration of the active ingredient. The results were reported in Table 5, where the control chemical? a commercially available fungicide (under the generic name of maneb) including manganese ethylene bis (dithiocarbamate). Percentage of lesion area in plot-Disease control {$>) - (1? ~ -)? 100 Percentage of lesion area in untreated plots Table 5 (Activities against cucumber) Compound Concentration Disease Control Fi tototoxicity? No? _ ... Ipm) _ ili 1 500 88 0 2 500 96 0 4 500 99 0 12 500 98 0 14 500 100 0 18 500 100 0 25 500 92 0 26 500 98 0 27 500 100 0 28 500 94 0 31 500 100 0 32 500 100 0 33 500 98 0 34 500 100 0 36 500 96 0 41 500 96 0 42 500 100 0 43 500 100 0 44 500 100 0 49 500 99 0 Chemical substance ^ QQ Q0 0 control ca J Untreated - 0 Experiment 5 Tests on the activity? Cucumber anthracnose fungicide Dilute formulations of a wettable powder containing the required concentrations of the active ingredient were prepared as described in Example 14. The test formulation? was applied at a rate of 10ml per pot to the leaves of cucumber seedlings (variety "Sagamihan jiro") at the true leaf stage, which were grown on soil in 9cm diameter cookie pots in a greenhouse. 3 pores of Collec totrichum lagenarium produced by incubation on a medium of oatmeal and agar at 24? G for 10 days were suspended in sterilized water containing 50 ppm of Tween 20 / to give a suspension having a concentration of spores CL which about 100 spores could be observed in an observation with a microscope or at 150 magnifications. One day after application, the treated leaves of the cucumber seedlings were inoculated by spraying them with the aforementioned spore suspension. The seedlings cos? inoculated were first placed in a humid chamber at 20 ° C for 24 hours and then kept in a greenhouse at 24 ° C to allow the development of the disease. Six days later the seedlings were removed from the greenhouse and? The percentage of lesion area per vessel was calculated. Control of the disease? was calculated by means of the following equation Number of lesions in Disease Control (jt) = (1 - treated plots _ Number of lesions in y.? Untreated plots Phytotoxicity? against the plants of cetr ^ ol? it was also evaluated with the same gradation reported in Experiment 1. The control of the maiat tia? an average value of the results of the tests conducted in two replicates at each concentration of the active ingredient. The results are reported in Labella 6, where the control chemical? a commercially available fungicide (under the generic name of Daconil) comprising tetrachloroisophthalonitiyl. Table 6 (Activities against cucumber anthracnose Compound Concentration Disease Control No. _ Imi. Phytotoxicity? _ (*) 2 500 88 0 4 500 97 0 9 500 94 0 12 500 98 0 14 500 100 0 17 500 100 0 18 500 100 0 22 500 98 0 25 500 96 0 27 500 100 0 30 500 99 0 31 500 100 0 35 500 98 0 36 500 100 0 39 500 100 0 41 500 94 0 43 500 100 0 Support who not with 500 98 0 trollo Untreated 0 Experiment 6 Tests on activity? fungicide against "powdery mildew" (Sphaerotheca fuliginea) of cucumber The test formulation containing the required concentrations of the active ingredient and prepared cc) me described in Example 14-? was applied at a rate of 10 ml per pot of tomato seedlings (various "Sekaiiehi" teas) at the three true leaf stage grown on soil in 9 cm diameter cookie pots in a greenhouse. The following day the seedlings were inoculated by spraying them with a suspension of Sphaerotheca fuliginea spores. Ten days after inoculation,? Was the percentage of the seedling lesion area and disease control assessed? was calculated by means of the following equation shown below. Phytotoxicity? against cucumber plants? it was also evaluated with the same strength defined in Experiment 1, at the concentration of the active ingredient. The results are shown in Table 7 where the control chemical? a commercially available liquid preparation (under the generic name of milcurb liquid) comprising 2-dimethylamino-4-methyl-5-butyl-6-hydroxy-pyrimidine. Percentage of lesion area in treated plots _ Disease Control ($) = (1?) X 100 Percentage of lesion area in untreated plots Table 7 (Activities against "mildew" (a) of the ce tri Compound Concentration Disease Control No. Phytotoxic t? _ LEESJ _ (?) 3 200 82 0 10 200 85 0 1 4 200 92 0 ' 17 200 96 0 22 200 94 0 26 200 100 0 28 200 98 0 33 200 100 0 36 200 100 0 39 200 100 0 40 200 100 0 41 200 100 0 42 200 100 0 44 200 97 0 45 200 100 0 46 200 99 0 47 200 100 0 Substance who not d ^. with troll 1 200 95 0 Untreated - 0 DESCRIPTION 1 TITLE OF THE INVENTION Derivatives of benzoxazolone and a fungicidal agent? bactericide containing said derivatives for use in agriculture and nettle cultivation? 2 SCOPE OF THE CLAIMS 1? A derivative of benzoxazolone represented by the general formula: or C = 0 R ~ COR in which;?? and R2 represent an alkyl group or 1 halogen atom, X represents a halogen atom and R? represents an alkenyl or alkenyloxy group? 2 A fungicidal or bactericidal agent to be used in agriculture and horticulture comprising as an active ingredient a derivative of benzoxazolone represented by the general formula or C = 0 / COR where R ^ and R? represent an alkyl group or a halogen atom, X represents a halogen atom and R ^ represents an alkenyl or alkenyloxy group? 3. DETAILED EXPLANATION OF THE INVENTION Does this invention relate to new benzessazolone derivatives and their use as a fungicidal or bactericidal agent in agriculture and horticulture? Pi? specifically, this invention relates to a new benzessazolone derivative represented by the general formula (I): O C = 0 (I) / COR wherein R ^ and Rg represent an alkyl group or a halogen atom? X represents a halogen atom and R = represents an alkenyl or alkenyloxy group, and a fungicidal or bactericidal agent for use in agriculture and horticulture containing this derivative as an active ingredient? We have synthesized a variety? of derivatives of benzessazolone and we have carefully studied their usefulness? in order to develop new fungicidal and bactericidal agents that have a low tos sicit? and good security and that they have a high activity? center a wide range of fungi and bacteria. As a result, we have now discovered new benzoxazolone derivatives represented by the aforementioned mineral c-D form (1), which exhibit excellent properties. as fungicides and bactericides for use in agriculture and horticulture? These compounds present that? a strong activity? antibacterial with tro a variety? of molds or fungi and bacteria and have a wide range of applications as a fungicidal and bactericidal agent in agriculture and horticulture. Therefore, if applied to a rice plant in a field with water, these compounds can protect the plant from contamination by brusene (Piricularia oryzae), from elmintosporiosis or sore neck of rice (Cochliobolus sdyabeanus), from "sheath blight" (Pellicularia sasaki), from "bacterial leaf blight" (Xanthomonas oryzae), etc. In a * application d? these compounds in the field of fruit growing,? It is possible to effectively protect the plant from diseases such as the "black spot" (Alternarla kikuchiana) of the pear, the "ripe rot" (Gl omerali a cingulata) of the vine, the black spots (Cladosporium fulvum) of the gold tomato, the downy mildew ( Phytophtora infestane) of the tomato, the "stem rot" (Sclerotinia sderotiorum) of the green beans, the "povdery mildev" (Sphaerotheca fuligcnea) of the cucumber, the "dovny mildev" (Pseudopero nospora cubensis) of the cucumber, the anthracnose (Colletotrichum lagenarium) cucumber, the "fusarium vilt" (Fusarium oxysporum) of the cucumber, the "soft rot" (Er or wines aroidea) of the Chinese cabbage and more? These com J ?! pests are also particularly active as ferti A lizzanti of the seed, for example against the white mold (Gibberella fujikuroi) of the rice, the elndntosporiosi ? rice neck sore (Cochliebblus miyabeanus), etc? Since? these compounds have a strong activity? fungicidal or antibacterial without damaging the useful plant to which the compounds are applied e without endangering humans, animals or fish, they represent an excellent fungicidal or bactericidal agent and can they be used freely? E * gi? known, as described in the descriptions of the German patents N? 1,023,627 and N? 1.147.007, that 4,5,7-trichlorobenzoxazolene and the like can be used as bactericidal and fungicidal agents in industrial applications? It is also known, as described in the description of the Russian patent N? 32801, that the 4,5,6-trichlorobenzoxazolone possesses a 'acts vit? antibacterial? In addition, the Japanese patent publication N? 23519/65 describes that 4 # 5? 6-trichlorobenzoxazolone which? been replaced on the R group in the formula (I) with my benzoyl group pu? be used as a fungicidal or bactericidal agent in agriculture and horticulture against the brusone of rice, the "fusarium blight" of soy, anthracnos? some cucumber9 etc? However, none of the above descriptions describe the 5v6,7-tri-substituted benzoxazolone derivatives according to the present invention, which are therefore novel compounds never described in the literature. The derivatives of benzoxazolone according to this invention possess an activity? fungicide or bat tericide considerably more? high compared to that? of the above derivatives 4 * 5t7-trichlorobenzoxazolone and 4? 5 * 6-trichlorobenzoxazolone? These new findings were made possible as a result of substitution with three substituents at the 5-? 6- and 7- of the benzene ring of benzoxazolone and would never be achievable by anyone ordinarily skilled in the art based on the prior art? ? compounds according to the present invention can be prepared by the following reaction scheme (a) or (b). Reaction Scheme (a) Re X OH O 0 = C / A \ or C = 0 R NHCR- B COR [II] I [III] In the general formula (il), R ^, R ^, X and R ^ have the same meaning as indicated above? Can the compounds of formula (II) be readily prepared from a corresponding orthoamine phenol substituted with suitable R ^, Rg and X and by a known method? In general formula (III), A and B, which can be the same or different, represent a halogen atom, an alkoxy group, a haloalkoxy group, an alkylthio group or an amino group? Examples of these compounds are? phosgenic compounds such as phosgene, diphosgene (trichloromethylchloroformate), eoe ?, halofermates, aleticiformates, carbonic diesters, urea and others? The reaction scheme (a) can? be considered as a two-step reaction comprising the reaction between compound (II) and compound (III) stopping an intermediate product with the elimination of the compound HA or HB and a subsequent further elimination of the compound HB or HA from the intermediate product? Therefore, if a stable intermediate product is formed depending on the nature of compound (III) used, it can be formed. be isolated and then heavenly to produce compound D (I)? Alternatively, such a stable internal product can? be synthesized with a different method without resorting to the reaction between compound (II) and compound (III) and then cielized? ^ The reaction between compounds (II) and (III) according to the reaction scheme (a) pu? be carried out in the absence of any solvent? but preferably in the presence of an organic solvent that can? also and? be an excess of the same compound (III)? Examples of usable solvent include hydrocarbons? halogenated hydrocarbons9 ethers? esters, acid starches, alcohols, dimet 3ulphoxide and the like? from which you choose glier? a suitable solvent according to the nature of the compounds (III)? An acid-binding agent can? be used in order to facilitate the reaction, as some compounds (ili) can lead to the formation of an acid during the reaction process? Does the acid-binding agent that can be used for this scope include organic nannins such as triethylamadna and pyrilynine? inorganic bases such as potassium carbonate? The reaction can? be carried out at a temperature of m? environment, although it can be completed in a short period of time if followed at a high temperature? At the end of the reaction the compound? Object of this invention can? be obtained by filtering a salt or salts of the precipitated acid-binding agent in the reaction mixture, in which? used the binder, which is followed by the distillation of the solvent from the filtrate. Alternatively, water and / or a suitable organic solvent such as benzene, chloroform? ete re and tetrahydrofuran pu? be added to the reaction mixture for fractionally extreme the compound of the invention? An example of the method according to the scheme of reaction (a)? reported more? below in Example 1? Reaction Scheme (b) (agent binder acid) O C = 0 R-.CY / 3 or C = 0 N ' COR [IV] [V] In the compounds of the formula (IV), R ^, Rg and X have the same meaning as indicated above? Can the compounds of the formula (IV) be prepared by reacting a substituted orthoaminophenol with R1? R2 and X with a compound of formula (III) according to the method of reaction scheme (a)? In the compound of the formula (V), R has the same meaning as indicated above and Y represents a halogen atom ?. These compounds are alkenoyl halides, alkene nyl al? Formates, etc? and can they be easily prepared with a method in itself? known? The reaction between compound (IV) and compound (V) according to the reaction scheme (b) can? be carried out in the absence of a solvent, but preferably in the presence of an organic solvent which can also be an excess of the same compost? (V)? Examples of the usable solvent include hydrocarbons, halogenated hydrocarbons, ethers, esters, ketones, acid starches, alcohols and dimethyl sulfoxide? As an acid-binding agent, organic animins such as triethylanmdna and pyridine and inorganic bases such as potassium carbonate can be used. be carried out at room temperature or, in a more? appropriate, high temperature? Will the required reaction time depend? obviously from the nature of the compound (V) used, the nature of the solvent and the reaction temperature, although it may decrease if the reaction is carried out in a polar organic solvent? For the recovery of the compound object of this invention at the end of the reaction, the resulting reaction solution can? be filtered to remove a salt of the acid-binding agent precipitated therein and the filtrate evaporated to obtain the desired compound? In certain cases? water and a suitable organic solvent such as benzene? chloroform? Can ether or tetrahydrofuran be added to the reaction mixture to extract the subject compound? An example of the method according to the reaction scheme (b)? shown below in Example 2? Are examples of the preparation of the compounds according to the invention given below? Example 1 Preparation of Compound N * 1 22.6 g of 3-chloro-6-acryloylamino-294-xylenol prepared from 3-chloro-6amino-2t4-xylenol and acrylollchloride were placed in a 300 ml round bottom flask9 to which 27 * were then added 6 g of anhydrous potassium carbo- nate and 150 ml of toluene? 9? 9 g of phosgene was introduced into the mixture under stirring and cooling in a water and ice bath. So the reaction mixture? been heated to reflux temperature for an ara? After cooling down? the reaction solution? was transferred to a separation funnel. With the subsequent addition of 150 ml of tetrahydrofuran and 150 ml of water and the organic layer so? format? been separated? dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent and leave yellow crystals? Recrystallization from acetone gave 20 * 4 g of white crystals of N-acryloyl-5 * 7-dimethyl-6-chlorobenzoxazolone with a melting point of 161-163? C? Example 2 Preparation of Compound N? 2 21.3 g of 6-amndno-2,3 * 4 ~ trichlorophenQlo * 27 * 6 g of potassium carbonate and 150 ml of toluene were placed in a 300 ml round bottom flask? 9 * 9 g of phosgene was introduced into the mixture under stirring and cooling in a water and ice bath? The resulting mixture? was heated to reflux temperature for an hour then cooled and transferred to a 500ml separating funnel, 150ml of tetrahydrofuran and 150ml of water were added to the funnel and the organic layer formed. been separated * dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent and leave 23 * 4 g of yellowish white crystals of 5 * 6 * 7-tr: L chlorobenzoxazolone? Recrystallization from a mixture of methanol and acetone gave white crystals with a melting point of 253-254 ° C? The crystals were placed in a 300ml round bottom flask, to which 150ml of acetone and 12v0g of chloroformed allyl were then added. Then 10.1 g of triethylamine was added dropwise to the mixture with cooling in a bath of water and ice? At the end of the addition to got ce # the mixture? been heated to reflux for one hour to complete the reaction, then the solution ~ zi one of reaction? been cooled and filtered to remove precipitated salts? The filtrate? been concentrated to obtain yellow crystals, which were recrystallized from acetone to produn e 27.4 g yellowish white crystals of N-allyloxy carbonyl-5,6,7-trichlorobenzoxazolone with a dot of fusion of 96-98 eC? The compounds of the general formula (I) prepared with the above examples have been illustrated in Table 1? Were the numbers of the compounds used also reported in the following examples? Table 1 Compound H? Structural formula Melting point (? CH? : There 0 c = 0 CH3 or \ 161 - 163 N / COCH = CH, O Vo 96 - 98 THERE / OOCH2CH = CH2 whether the compounds according to this invention are used as a bactericidal or fungicidal agent for use in agriculture and horticulture? can they be used as such or prepared in the form of a water-wettable powder? solution? emulsion? sol? powder (including DL type powder)? granules? grains? etc?? diluting with a liquid carrier such as water and an organic solvent or a solid powder or other appropriate carrier? And? if necessary? adding an auxiliary agent such as a wetting agent? spreader? dispersant? emulsifier? adhesive? etc? Can water as examples be given as liquid baicels to be used in the preparation of the compounds? aromatic hydrocarbons? aliphatic hydrocarbons? alco & C? este ri? ketones? acid starches? dimethyl sulfoxide? etc? Can mineral powders such as clay be used as solid vehicles? talc? kaolin? bentonite? diatomaceous earth? calcium carbonate? silicic acid? etc? and organic poiveri such as wood dust and more? As agent ^; auxiliary? will it be possible to mention nonionic, janionic, cationic and ampholytic type surfactants? lignosulfonic acid and its salts? tires? aliphatic salts? methylcellulose and other pastes? furthermore? the compounds according to this invention? if used as a fungicidal or bactericidal agent for use in agriculture and horticulture? can they be prepared to incorporate an insecticide, fungicide, bactericide, herbicide, plant growth regulator, etc. in order to expand 1? applicable t? o In some cases, there? to expect a strong synergistic effect if used in combination with other fungicidal or bactericidal agents? The following are examples of fungicidal and bactericidal agents which can be used in combination with the compounds according to the invention? Carbamate fungicides such as 3,3'-ethylenebis (tetrahydro-4,6-di? Efcyl * -2H-1, 3,5? Thiadiazine-2-ten); zinc or manganese ethylene bis (dithiocarbamate); bis (dime tildi oearbammoyl) disulfide; zinc propylene bis (dithiocarbamate); bis (dimethyldithioearbamoyl) ethyl diamndna; nickel dimethyl dithiocarbamate! methyl 1- (butylcarbamoyl) -2-benzinddazolocarbamate! 1,2-bis (3-methoxycarbonyl-2-thioureid) benzene; 1-isopropyl carbamoyl-3- (3, 5-dichlorophenyl) hydantoin; potassium N-hydrpssimethyl-N-methyldi thiocarbaupnate; 5-methyl-1 O-bu toxicarbonylamino-10,11-dehydrodibenzo (b, f) azepine etc ?; pyridine fungicides such as zinc bis (1-hydro? si-2 (1H) pyridinationate), 2-pyridinol-1-sodium salt oxide, etc ?; cerne phosphorus fungicides 0,0-diiso propyl S-benzylphosphorothioate; O-ethyl S, S-diphenyldithium phosphate, etc? ; phthalimide fungicides such as N- (2,6-diethylphenyl) phtaliad.de} N- (2,6 ~ diethylphenyl) -4 ~ methyl ^ phthalimide, etc? } dicarbessimide fungicides such as N-trichloromethyl thio-4-cyclohexene-1,2-dicarboxin; N-tetr acl oroeti 1 ti 0-4? cid ohexene-1 92-di c arbossind.de, etc. di dro-2-methyl-1 94-oxatin-3-carboxyanilide9 etc?} naphthoquinone fungicides such as 2,3-dichlor? -1, 4-naf toc hi none, 2-oxy-3-chloro-1,4- naf toquinone sulfate of rajne9 etc? } pentachloronitrobenzene} 1,4-dichloro - 2, 5 ~ dimethoxybenzene} 5-methyl-s-triazol (3t4-b) benzo thiazole} 2- (thiocyanemethylthio) benzothiazole} 3-hydroxy - S-methylisoxazol?} acid- N-293-dichlorophenyltetrachl roftaiand.no} 5-ethoxy-3-trichloromethyl-1 -2 94-ti adi azo lo} 2,4, 6-dichloro-6- (0-chloroanilino) -1, 3,5-triazine } 2,3-diciano-1,4-dithioanthraquinone} copper 8-oxycbino linatp} polyox? Na} varidamycin} cyclohexind.de} meta noarst? Born of iron} diisopropyl-1 v3-dithielane-2-iri denem ^ lonate} 3-allyloxy-1,2-benzolsotlazelo-1,1 - dioxide} kasugamycin} Blasticidin 3} 4,5,6,7-tetrachlorofthalide} 3- (3,5-diclorephenyl) -5-ethenyl-5 -methyloxyzolysine-2,4-dionej N- (3,5-dichlorophenyl) -1, 2-dimethyl cycloprepane-1, 2-dicarboxind.de} s-n-butyl-S '-para-t - bu tiibenzi 1 -H- 3- laugh at you, you'll be scared! limi data} 4-cl oro f enos pi- 3, 3-dimethyl-i - (1H9193, 4- tri azol-1 -yl) -2-but a none} methyl-D9L-N- (296-dimethylphenyl) -N - (2 * -methoxyacetyl4 alaninate j N-propyl-N- [2- (2? 4? 6-trichloro? Enoxy) ethylJ inddazol-l -carbossarand.de j N- (3? Orophenyl willows) succi niuddej tetradoroisoftalonitrilef 2- dimethylamines - 4-methyl-5-n-butyl-6-hydroxypyrimidine | 2,6-dichlore - 4-ni troaniline j 3-methyl-4-chlorobenzothiazole-2-? ne; 1 f2t5 #? - tetrahydro-4H -pyrrole | H3? 2? 1-i, j J quinoline? -2-onej S'-isopropoxy - ^ - methylbenzalinidej 1- [2- (2? 4 ~ -dichlorophenyl) -4-ethyl-1 f 3- dioxelane-2-ylmethyl] -IH? 1? 2? 4? triazoloj 1, 2-benzisothiazelina-3-onej basic copper chloride f basic copper sulphate y N * -dici? wastewater romethylthio-N? N-dimethyl-N -phenyl sulfanmd.de | ethyl-N - (3-dimethylaminopropyl) thiocarbamate hydrochloride; piondcinaj S? S-6-methylquino3saline-2,3-diildithiocarbamate; complex of zinc and manebj of.-zinca bis (dime tildi) thiocarbamato ethylene bis (of thiocarbamate)? There is no reason to limit the fungicidal agent or bactericidal agent to those described above? Examples of plant growth regulators? herbicides and insecticides which can be used in combination with the compounds of this invention? include the following! Plant growth regulators based on iso urea such as N-methoxycarbonyl-N, -4? methyl enylcarbam? il_ ethyl sourea? i- (4-chlorophenylcarbamoyl) -3 ~ ethoxycarbo nyl-2-methylisorurea, etc.j another type of plant growth regulator such as sodium naphthalinacetate; 1 f2-dihydr? Pyridazine-3,6-dionej gibberellins, etc? ; herbicides based on d? triazine such as 2-methylthi - 4,6-bisethylarandno-1,3 * 5-triazine; 2-methoxy? 4-ethylamnri.no-6-isopropylBmu.no-1 f 3 # 5-triazine; 2-chloro-4-ethyl annri.no-6-isopropylainndno-s-triazine; 2-methylthio-4,6-b? S (isopropylamnri.no) -s-triazine; 2-methylthio-4-ethyl amino-6-is? Prepylamino-s-triazine, etc? ; phenhexis - herbicides such as 2, 4-dichlorophenos si acetic acid and methyl, ethyl and butyl esters thereof; 2 - chloro-4-methylphenoxy acetic acid; 4-chloro-2-methyl phenoxy acetic acid; ethyl 2-methyl-4-chlorophenoxybylate etc ?; diphenylether-based herbicides such as 2,4f6-tri chlorophenyl-4'-nitrophenylethereth 2,4-d? cl? rofenyl-4 ,? -nitroph enylether; 3f 5-dimethylf enylM'-nitrophenylether etc ?; urea herbicides such as 3- (3,4 ~ dichloro? enyl) - 1-methoxy-1-methyl urea; 3 '- (3? 4-dichlorophenyl) -1.1 - dimethylurea; 3- (4-cl? Rofenil) -1, 1-dimethyl urea etc? ; herbicides, carbamate I such as 3-methoxy? carbonylaminophen? 1-N- (3-methylphenyl) carbamate; isopropyl-N- (3-chlorophenyl Jcarbamate; methyl-N- (3,4, -dichloro? enyl) carbamate, etc?; uracil herbicides such as 5-bromo-3-sec - butyl-6-methyluracil ; 1-cyclohexyl-3 # 5-propylene urea Chile, and ^ c?; Thiolcarbamate herbicides such as S- (4-cl? Robenzyl) -N # M-diethylthiolcarbamate; S-ethyl-N-cyclohexyl-N-ethylthiolcarbamate; S-ethyl-hexahydro-1H-azepin-1 - carbothiaate; S-ethyl-N, N-di-n-propyl or arb-cored etc?; Pyridinium herbicides cerne 1-1, -dimethyl-4,4 * - chloride bispiridinium, etc. toluidine; 4- (methylsulfonyl) -2f6-dinitro-N, N-d? propyl aniline; N3, N3-diethyl-2,4-dinitro-6-trifluoro methyl-1,3-phenylene-di amine, etc. dichloropropionanilide, etc?; er ~> pyrazole cides such as 1,3-dimethyl-4- (2, 4-dichloroben zoyl) -5-hydroxypyrazole; 11 3-dimethyl-4- (2,4-dichloro benzene) -5- (p-tolueneesulfonyl9ssi) pyrazole etc? ; other types of herbicides such as 5-tert-butyl-3- (2,4-dichloro - 5-isopropoxyphenyl) -1, 3,4-oxadiazoline-2-one; 2 - jk-isopropyl, N- (4-elorophenyl) carbamoyl ^ -4? chlorine? -5-methyl-4-isoxazoline-3-one; 3-isopropyl-benzo-2 - thia-1,3-diazinone- (4) -2, 4-dioxide; 3 - ('2-methylphenoxy) pyridazine, etc ?; phosphoric insecticides such as 0.0-diethyl 0- (2-isopropyl-4-methyl-6-pyrimidinyl) phospho rotloate; 0,0-diethyl S-2- ^ (ethylthio) ethyl phosphorodthioate; 0,0-dimethyl- 0- (3-methyl-4-nitrophenyl) thiophosphate; 0,0-dimethyl S-? N-methyU-earbaraoylmethylphosphorodi ^ thioate} 0t0-dimethyl S- (N-raethyl-N-formylcarbemeylmethyl) phosphorodithioate} OfO-dLimethyl S-2- jT (ethyl) ethylJ ^ f? Spheroditio 0,0-diethyl S-2-? (Ethylthio) ethyl phosphorodithioate} ofO-dimethyl-1-hydr? Ssi-2t2t2-tricl? Rai ethylphesf? Nate * 0 # 0-diethyl-0- (5-phenyl-3 -is? ssazolyl) phosferothioate} 0,0-dimethyl 0- (2 # 5-dichloro-4-bromofe nyl) phosferothioate} 0 # 0-dimethyl 0- (3-raethyl-4-? ethyl> mercaptophenyl) thiophosphate} O -ethyl O-p? cyanophenyl phenylphosphorothioate} OfO-dimeth? l-S- (lf2-dicarbeetessethyl phosphorodithioate; 2-cl? ro- (2 # 4? 5-trichlorephenyl) vinyl dimethyl phosphate} 2-chlor? -1- (2,4 -dichlorophenyl) -vinyl dimethyl phosphate} 0,0-diaethyl O-p-cyanophenyl phosph? roti? atoj 2,2-dlchlorovinyl dimethyl phosphate} 0,0-diethyl 0-2,4-dichlorophenyl phosferothioate; ethyl mercaptophenyl acetate; 0-dimethyl phosphorodithioate; S- ^ (6-el? Ro-2 - oxor3fben20ssazplinil} metiiJ 0f0-diethyl phosphorodithio to; 3-chloro-1- (294-dicleroienyl) vinyl diethylphosphate, 0,0-diethyl 0- (3-oxo-2- fenik-2H-pyridazine-6-yl) phosferothioate} o9o-dimethyl S- (1-jtaethyl-2-ethyl-sulfinyl) - ethyl phosferothioate} 0,0-dimethyl S-phthaliraidomethyl feforpdithioate} 0? 0-diethyl S - (N-ethoxy-carbonyl-N-methyl ^ carbameylmethyl) phosferodithioate} 0t0-di? Ethyl s- ^ 2-rae toxo-1 # 3 # 4-thiadiazole-5- (4H) -onyl- (4) methyl J dithiophosphate; 2-methoxy-4H-1, 3,2-benzedioxyphersine 2-sulfide} 0 # 0-diethyl 0- (3 # 5 # 6-trichloro2-pyridyl) phosphorus thioate O-ethyl 0-2, 4-dichlorophenyl thionobenzene phosphonate) S-? 4 * 6-diaramino-s-triazine-2-yl-methyl J 0.0 - dimethyl phosphorodithioate; 0-et? L 0-p-nitrophenyl phoni! phosphorothioate; 0, S-diraethyl N-acetyl phosphoramidothio to) 2 -die t il aramino-6-methylpyrimidine-4-yl-diethyl-phosph erotic? Born) 2-diethylamin? -6-methyipyrimidine-4-yl-dimethyl? phosphorothioate) 0,0-diethyl O-p-Cmethylsol phonyl) phenyl phosphorothioate) O-ethyl S-propyl 0-2,4-dichlorophenyl phosph erodedate; ? is-3- (dimeth? ssifesfin ?? si) N-methyl-cis-cr? tone amide) carbamate insecticides such as 1-naphthyl N-methylcarbammat?) S-methyl N-? methyl carbam? l-oxy ~ J thioacetoinddate) m-tolyl methylcarb <_n born; 3,4-xylyl methylcarbamate) 3,5-xylyl methyl ar baramate) 2-sec-butylphenyl N-methylcarbamate) 2,3 - dihydro-2, 2-dimeth 1-7-benzofur anilraethylcarbanoaate) 2-ieopropoxyphenyl-N- raethylcarbamate) 1,3-bis (carbamoyl thio) -2 (N fN-dime ti 1 amadxio) -propane hydrochlorar? ) 2-diethyl aranine-6-raethyl pyridine-4-yl-dimethylearbamate, (; e; cc?) Other insecticides such as? > N, N-diraethyl-N? - (2-methyl-4 ~ chlorophenyl) formamidine hydrochloride, sol, fato d; L nicotine, ndlbemicin, 6-methyl-2,3-quinoxal nadithiocyclic S, S-dithiocarbonate , 2,4-dinitro-6-sec - butyl- phenyl diraethyl acrylate 1,1-bis (p-chlorophenyl) 2,2,2-trichloroethanol) 2- (p-tert-butylphenoxy) isopro pil-2 * - chloroethyl30lphite) azoxybenzene di- (p-chloro / eniij-cyclopropyl carbinol; di? tri (2? 2-dimethyl- A -2-phenylethyl) tin ^] oxide; i- (4-chloro? enyl)> - 3- - (2, ^ - difluorobenzoyl) urea; S-trichloroesylstagn? 0? 0-diisopropylphosphorodithioate? Etc ?; or fertilizers? Etc, ? This invention? further illustrated but not limited by the following examples? in which the parts sine by weight0 Example 3 Formulation of emulsion An emulsion formulation containing 20% active ingredient? been prepared by homogeneously dissolving and mixing 20 parts of compound N.1t 30 parts of dimethylforraararaide? 35 parts of xylene and 15 parts of polyoxyethylene alkylaryl ether * Example 4 Formulation of sol a sol formulation containing 40% active ingredient? been prepared by homogeneously mixing 40 parts of compound N? 2 ground to a particle size less than ?? ^? ? 2 parts of sol, fate, lauryl? 2 parts sodium alkylnaphthalene sulfenate? 1 part of hydro | sipropylcellulose and 55 parts of water? Exempt it 5 Wettable powder formulation jA wettable powder formulation containing 2 <j)% active ingredient? been prepared by raacinando and mixing homogeneously 20 parts? of compound No. 1, 5 parts of polyoxyethylene alkylary ether, 3 parts of calcium lignosulfonate and 72 parts of diatomaceous earth. Example 6 Powder formulation A powder formulation containing 30% active ingredient? been prepared by grinding and homogeneously mixing 3 part? of compound No. 2, 0.5 parts of silica fine powder, 0.5 parts of calcium stearate, 50 parts of clay and 46 parts of talc. Example 7 Granular formulation A granular formulation containing 5% active ingredient? was prepared by grinding and homogeneously mixing 5 parts of compound N.2, 1 part of calcium lignosulfonate, 30 parts of bentonite and 64 parts? of clay, granulating the ground mixture, drying? granules and passing the dried granules through a sieve to obtain the desired granule size. Test 1 Test to establish the activity? fungicide against helminthosporiosis or rice neck pain A wettable powder formulation prepared as described in Example 5? been diluted with water to obtain test formulations containing the required concentration of active ingredient. The test wording? been applied to the plants of aquatic rice (variety "Asahi **) at its sta god of four foliages, which have been grown on earth in biscuit vessels of 9 cm in diameter? three in a greenhouse. One day after 1 * application, 1; treated seedlings were inoculated by spraying them with a suspension of Cochliobolus miyabeanu spores (elminthosporiosis or rice neck pain). Five days after 1? Inoculation,? The number of lesions detected per leaf at the four-leaf stage was evaluated and the control (%) of the disease was calculated with the following equation. Phytotoxicity? against rice plants? state fis sata also with the following gradation. Control of the disease? an average value of the results of the tests which were carried out in two replicates at each concentration of the active ingredient. The results are shown in Table 2. Number of lesions in Disease Control (#) = (1 - treated plots x 100 Number of lesions in untreated plots Phytetoxicity rating grade t 5: Severe damage 4s Great damage,. 3: Damn? moderator # 2 * Minor damage? 1t Negligible damage? 0> No damage? Table 2 Compound N fungicidal effect against neck pain? Concentration Disease control Phytotoxicity? _ (PP?) _ (?) _ 1 500 100 0 2 n 100 0 Control A "32 3 ? B H 54 4 w C "25 2 "D" 30 1 triazine "94 0 Untreated 0 the (Note) \ JJ A: (German Patent No. 023 * 627) ? \ C * 0 /, Cl H ; there CA. BX? , i \ C? Q n (German patent ?? 1.1 47? 007) / ? C? H. C: c = o (Japanese Patent Publication Co O / ~ Ci No. 23519/65) There 0 D: \ c = o (Ci o N / Japanese Patent Publication No. 23519/65) Ci I co <?> a ? Triazina (?? commercial product) Cl *> N -O ffl? / OR / Test 2 Test to evaluate the activity? fungicide against rice blast. A formulation d? wettable powder prepared as described in Example 5? been diluted with water to obtain the formulation d? test containing the required concentrations of the active ingredient and the test formulation? been appli cata on aquatic rice seedlings (variety? "Asahi") at the stage of three leaves, which were grown in the ground, in biscuit containers of 9 cm in diameter in a greenhouse? One day after application, the treated seedlings were inoculated by spraying Eec with a suspension of Piricularia or ^ zae spores and incubating in a humid chamber (relative humidity of 95 - 1005 ?, and temperature of 24 - 25eC :) * Five days after the inoculation,? been evaluated the number of brusone lesions per leaf per sta god of three leaves and disease control (%)? been calculated with the following equation? Phytotoxicity? against rice plants? been assessed in the same way as in Test 1? Proof ? was carried out in two replicates for each concentration of the active ingredient. Are the results shown in Table 3? Number of lesions in treated plots Disease control (%) = (1 -? Y xlOO Number of lesions in untreated plots Table 3 Fungicidal effect against brusone of rice Compound N. Concentration Disease control F? Totossicit? (?? *> _? * 1 1 200 100 0 100 0 Control A "52 1 "B" 63 2 ? C "48 1 "D" 51 1 ? IBP 480 76 0 Untreated - 0 (Note) 0 IBP: (? -C3H7O) 2P-SCH2 O Test 3 Test to evaluate 1 * activity? fungicide against downy mildew A wettable powder formulation prepared as described in Example 5? been diluted with water to obtain the test formulations containing the required concentrations of the active ingredient. The test wording? been applied at a rate d? 10 ml per container on young tomato seedlings (variety "Sekaiichi") at the stage of three true leaves, which have been grown on the ground in biscuit containers with a diameter of 9 cm in a greenhouse? Spores of Phytophthora infestans produced on potato tubers have been suspended in sterilized water to give a spore concentration to the which 20 - 30 spores could be revealed in an observation with a microscope at 150 magnification, One day after the application, the leaves of the seedlings d? tomato were inoculated with drops of the spore suspension and the seedlings were kept at 20 ° C in a humid unaoameaa to set the development of the disease. Three days later, the seedlings have been removed from the room .ed? the number of leaves attacked was counted. The percentage of leaves attacked and the disease control (?) Were calculated with the following equations. Phytotoxicity? against the tomato plants? was also evaluated with the ste_s sa gradation as defined in Test 1. Number of leaves attached Percentage of leaves _ x100 attached Number d? inoculated leaves Percentage of leaves attacked in treated plots Disease control ($) = (1 - tati_) xioo Percentage of leaves attacked in untreated plots Proof ? was carried out in two replicates for each concentration of the active ingredient. I re The results are shown in Table 4. Table 4 Fungicidal effect against tomato blight. Compound N. Concentration Disease control Phytotoxicity? IPEEL 111 1 500 100 0 2 100 o Control A 0 0 ? B 0 0 C 0 0 D 0 0 Maneb 87 0 Untreated (Note) Maneb i CH ^ HNCS Mn CH.HNCS Test 4 Test to evaluate the activity? fungicide against cucumber "downy mildev" (Pseudoperonospora cubensi3). A wettable powder formulation prepared as described in Example 5? been diluted with water to obtain the test formulations containing the required concentrations of the active ingredient, and the test formulation? been applied at a rate of 10 ml per vessel to the outer surface of leaves of young cucumber seedlings? spores of Fseudoperonospora cubensis produced on cucumber leaves in a greenhouse (variety "Sagamihanjiro '?) at the stage of a true leaf, which have been grown in terr? environment of development of the disease were removed with a brush in deionized water containing 50 ppm of Toeen 20 (polyoxyethylene sorbitan monolaurate) in order to give an ino ass having a concentration of spores at which 20 - 30 spores were detectable; with a observation under a microscope at magnification 150? One day after application, the leaves of the cucumber seedlings were inoculated on their lower surface treated by spraying with the inoculum. At the end of the inoculation, the seedlings were first placed in a humid chamber at 20 ° C for 24 hours and then kept in a greenhouse at 24eC to allow the development of the disease? Six days later, the cells were removed from the greenhouse and the percentage was evaluated of the lesion area found per vessel? Disease control (?) ? been calculated with the following equation? The phyto toxicity of cucumber plants? been evaluated also with the same gradation as test 1? There trial ? was carried out in two replicas for each na concentration of the active ingredient and from there? ? Was the mean disease control calculated? THE test results are shown in Table 5? Percentage of lesion area in ill-suited treated-Control plots a (%) = (1 - ^ xlO Percentage of lesion area in untreated plots? Table 5 Center fungicidal effect of Pseudoperonospora cubensis in cucumber? Compound No. Concentration Disease Control Pitotoxicity? _ ._ _? PPm? _ _ in _ 1 500 100 0 2 ? 100 0 Control A "20 1 "B" 25 1 ? C? 30 1 M D "36 1 ? Maneb? 90 0 Untreated 0 Test 5 Test to evaluate the activity? fungicide against anthracnose and cucumber. A wet powder formulation prepared as described in Example 5? been diluted with water to obtain test formulations containing the required concentrations of the active ingredient and the test formulation? was applied at a rate of 10 ml per container to the leaves of young cucumber seedlings (variety "Sagamihanjiro") at the stage of a true leaf, grown in the ground in biscuit containers with a diameter of 9 cm in a greenhouse. Spores of Collectotrichum lagenarium produced by incubation on an agar medium and oatmeal at 24 ° C for 10 days were suspended in sterilized water containing 50 ppm of Tween 20 ^ in order to give a suspension of a concentration of spores to which one about 100 spores could be detected on observation with a 150 magnifying microscope. One day after application, the treated leaves of the cucumber seedlings were inoculated by spraying with the aforementioned spore suspension. Subsequently, the seedlings were first placed in a humid chamber at 25? C for 24 hours and then kept in a greenhouse at 24? C to allow development. bit of the disease. Six days later, the seedlings were removed from the greenhouse and? the percentage of the lesion area found per leaf was evaluated. Disease control (%)? calculated with the following equation. Number of lesions in treated plots Disease control (%) = (1 - _ _ _) x100 Number of lesions in untreated plots Phytotoxicity? of cucumber plants? was also evaluated with the same gradation as Test 1, La prova? was carried out in two replicates for each concentration of the active ingredient and by there? ? the mean control of the disease was calculated. The results of the test are reported in Table 6, Table 6 Fungicidal effect against cucumber anthracnose. Compound N, Concentration Disease Control Phytotoxicity? _ LEHiJ _ ?? 1 _ 1 500 100 0 2 "100 0 Control A? 45 1 H B? 37 1 The c II 35 1 The D "43 1 "TPN? 98 0 Untreated - 0 (Note) C ?. f TPN * O I 9l CJl CN Test 6 Test to evaluate the activity? fungicide against cucumber "pewdery mildew" (Sphaerotheca fuliginea)? A wettable powder formulation prepared as described in Example 5? been diluted with water to obtain test formulations containing the required concentrations of the active ingredient ^ and the test formulation? was applied at a rate of 10 ml per container to young seedlings of cetriol (variety "Sagaraihanjiro") at the stage of a true leaf, which were grown in the ground in biscuit containers with a diameter of 9 cm in a series ra? The day after the treated seedlings are you inoculated by spraying with a spore suspension of Sphaerotheca fuliginea? Ten days after inoculation, the percentage of the localized lesion area and disease control (%) was evaluated? Calculated by means of the following equation? Was the phytotoxicity of ketrio plants also evaluated with the same gradation as in Test 1? The results are shown in Table 7 Percentage of the area d? lesion in treated plots Disease control ^) = (1 -) X10 Percentage of the area of l? Stion in untreated plots Table 7 Fungicidal effect against "poTwlery nrildew" some cucumber? Compound N? Concentration Control disease Phytotoxicity _ _ _ the} _ 200 100 0 100 0 Control A M 20 1 ? B n 10 1 ? i c? ' 10 1 "D" 13 1 "Dim -r? Mol" 95 0 Untreated 0 n-C (Note) 4H9! CH H D? Metir? Mol: Test 7 Test to establish the activity? fungicide? a ntibacterial against a variety? of fungi) bat te re phyto-pathogenic? Proof ? been conducted following the agar dilution smear method (strip method)? That is, a potato infusion medium (pH 5.8) for mushrooms or an agar broth medium (pH 7.0) for bat. teri which contains a required concentration of active compound under test? was inoculated by means of a platinum loop with a spore suspension obtained by adding sterilized water to a test microorganism. been incubated on an ind i ned area of the medium in a test tube? Further incubation of the inoculated medium? was carried out for 48 hours at 24? C for fungi and at 28? C for bacteria? Therefore, ? the growth of the microorganism was observed and? Has the minimum concentration (minimay inhibitory concentration <^ g / ml) of the active compound under test been determined? The results are shown in Table 8 phytopathogenic fungi or bacteria Effect Minimum inhibitory concentration (/ tg / ml) Compound No. 1 2 Control Fungi or phytopathogenic bacteria x. A B C D Cucumber "Fusarium wilt" (Fusarium oxysporum) <2.5 <2.5 <20 <20 <20 <20 "Leaf mold" of the tomato (Cladosporium fulvum) <2.5 <5 <20 <2oc0 or <20 <20 V. Rice "Bakanae disease" (White mold) <2.5? <2.5 _ <20 <20 <20 <20 i "Ripe rot" of the vine or (GlomereIla cingulata) <20 <20 <20 <? <1.25 <20 the "Black spot" of the pear (Alternate Kikuchiana) <5 <5 <40 <40 <40 <40 Rice "blast" ((.Piricularia oryzae) <1.25 <1.25 <20 <20 <20 <20 "Brown spot" of rice (Cochliobolus miyabeanus) <2.5 <2.5 <20 <20 <20 <20 "Soft rot" of Chinese cabbage (Erwinia aroidea) <10 <10 <160 <80 <160 <80 "Bacterial spot" of the cucumber (Bacteriosis) <10 <10 <160 <160 <80 "Bacterial leaf blight" of rice? ro (Xanthomonas oryzae) <10 <10 *? JIV <40 <40 TO Bit TO! BIT Test 8 Test to evaluate 1 * activity? fungicide against rice "sheath blight" (Pellicularia sasaki)? Diluted formulations each containing one with required contraction of an active compound in preva were applied at a rate of 40ml per three pots to the six-leaf stage rice seedlings, which were grown in soil in 9cm cookie pots. diameter in a greenhouse? The next day, 1? Inoculation of the seedlings with fungal disease? was carried out by placing an agar disk on the second sheath of the leaf obtained by piercing the edge of the colony of the Pellicularia sasaki fungus with a 5 mm diameter cork tip incubated on a medium of sucrose potato agar at 27eC for 48 hours * The inoculated seedlings were they then kept overnight in a wet room? Four days after inoculation,? the length of lesions per trunk was evaluated and? Has disease control been calculated by comparing the result of the untreated plots? Are the results shown in Table 9? Length of lesions in treated plots Disease control (?) = (1. Length of lesions in untreated plots Table 9 Compound N, Concentration (ppm) Disease Control (%) 1 500 100 2 500 90 Control A 15 B 0 10 0 Validamycin 125 90 Untreated 0 The Italian text written above? the faithful translation of the attached certified copy?