DE2354873A1 - FUNGICIDE AGENTS AND THEIR USES - Google Patents

Description

Priority: November 2nd, 1972. Japan, No. 109 890/72 '30. November 1972, Japan, No. 120 436/72 November 30, 1972, Japan, No. 120 437/72

The invention relates to fungicidal agents, ordering from 0.1 to 90 percent by weight of at least one 3,5-dichlorophenyl compound of the general formula I.

(D

■ in which A is a methylene group or an oxygen atom}

1 ■ 2

R is a hydrogen atom and R is a hydroxyl group or the remainder of Olle, where Me is an alkali metal atom, or R and

2 ■■ '"". · ■

R together represent a bond with the formation of an imide ring,

. as well as usual carriers, thinners and other _j

409 820/1 15 5

-Z-

Auxiliary materials.

The compounds of the general formula I have the formula I a or Ib '

(I a)

or

(I.

where A and R have the aforementioned meaning.

The compounds of the general formula I a are to compounds of the general formula I a ..

(I.

in which He has the aforementioned meaning, that is, to 3- (3 'j 5' -Dichlorophenylcarbamoyl) -norbornai-2-carboxylic acid and

their alkali metal salts,

or to compounds of the general formula I a ₂

409820/1155

(I a ₂ )

in the TT has the aforementioned meaning, that is, to 3- (3 ·, 5'-dichlorophenylearbamoyl) -7-oxate) icyclo- ^, 2,1) -heptane-2 ~ carboxylic acid and its alkali metal salts. '

The compounds of the general formula I b are N- (3 ', 5'-dichlorophenyl) -norldornane-2, 3-diearboximide of the formula I Ta ₁ .

1 '

(I.

or around N- (3 », 5 ^l -dihlophenyl) -7-oxabicyclo- (2,2,1) -heptane-2,3-dicarboximide of the formula I bp

(I.

409 820/1155

The remainder of me can be, for example, a Nectrxum • potassium atom Act. The compounds of the general formula I have pronounced fungicidal activity against phytopathogens Fungi and are practically non-toxic to harvested plants, mammals and fish.

In the 3 »5-dichlorophenyl compounds of the general formula I. These are well-known compounds used in veterinary medicine Find use (see US Pat. Nos. 3,215,597 and 3,261,845). In addition, it is known that N-4-fluorophenyl-3,6-epoxyhexahydrophthalimide, which does not fall under the compounds of general formula I, but has a similar chemical structure, has acaricidal activity (see US Pat. No. 3,261,845). In the entire literature, however, there is not the slightest hint contain that the 3> 5-dichlorophenyl compounds of the general Formula I have fungicidal activity, in particular against phytopathogenic fungi.

As a result of extensive research, it has been found that the 3,5-dichlorophenyl compounds of the formulas I a and I b. have a surprisingly high fungicidal activity against phyto-pathogenic fungi, for example Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, Piricularia oryzae, Cochliobolus miyabeanus or Pellicularia sasakü, and that the N- (3S5 ¹ -di-chlorophenabyl) -7-ox - (2,2,1) -heptane-2,3-dicarboximid has a pronounced fungicidal activity exclusively against the Sclerotinia and Botrytis species. It has been found that the 3p5-dichlorophenyl compounds of the general formula I'not

409820/11 SB

Phyto-toxicity to crops develop when in Amounts applied that are sufficient to urir a fungicide To ensure activity. In addition, it has been found that the compounds of the general formula I have an extremely low toxicity towards mammals and fish. ■

A number of connections are known to be made with the 3,5-dichlorophenyl compounds of the general formula I with regard to the chemical structure are closely related; your fungicide However, activity is so weak that any practical use is excluded. ■ ".. '·

The fungicidal agents of the invention "are present, for example, in the form of dusts, wettable powders, emulsifiable concentrates, sprays, aerosols, fumigants, pellets or granules, which contain at least one compound of the general formula I, either alone or in combination with one or more In addition to the 3,5-dichlorophenyl compounds of the general formula I, the fungicidal agents of the invention can contain one or more known fungicides. Suitable fungicides are, for example, blasticidin S, Kasugamycin, polyoxin, cellocidin, chloramphenicol, validamycin, streptomycin, griseofulvin, cycloheximide, pentachloronitrobenzene, pentachlorophenol and its salts, '2,6-> dichloro-4-nitr _Oarl iii _n} zinc ethylenebis- (dithiocarbamate), zinc carbamethyl

. 409820/1155

- c - ■ 'π

len-bis-Cdithiocarbanioyl), bis- (diraethylthiocarbanioyl) -disulfid, ■ 2,4,5,6-tetrachloroisophthalonitrile, 2,3-dichloro-1,4-naphthoquinone, Tetrachloro-p-benzoquinone, tetrachlorophthalide, p-dirnethylaminobenzoldiazonatriumsulfonat, 2- (1-methylheptyl) -4,6-dinitrophenyl crotonate, 2-heptadecylimidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -S-triazine, Dodecylguanidine acetate, 6-methyl-2,3- quinoxalinedithiol-cyclo-S, S-dithiocarbonate, N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide, N- (1,1,2,2-tetrachloroethylthio) -4-cyclohexene-1,2-dicarbpximid, 3- (3,5-dichlorophenyl) -5,5-dimethyloxazolidinedione-2,4 ', N- (3, 5-dichlorophenyl) maleimide, N- (3, 5-dichlorophenyl) -succini <mid, N- (3, 5-diclilorphenyl) -itaconimide,

2,3-dihydro-5-earboxanilide, 6-methyl-1,4-oxazine, 1- (N-butylcarbamoyl) -2-methoxycarbonylaminobenzimidazole, 2- (4'-thiazolyl) -benzimidazole, 1,2-bis- ( 3 (ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2-thioureido) -benzene, 2-amino-5-mercaptothiadiazole, 2-arainothiadiazole, O-butyl-S-benzyl-Sat ethyldithiophosphate, O-ethyl-S, S-diphenyldithiophosphate, 0,0-diisopropyl-S-benzyldithiophosphate, 0,0-dimethyl-O- (3-methyl-4-nitrophenyl) -dithiophosphate, S-Ji, 2-bis- (ethoxy carbonyl) ethy IJ-O, O-dimethyldithiophosphate, O, O-diraethyl-S- (N-methylcarbamoylmethyl) -dithiophosphate, O, O-diethyl-O- (2-isopropyl-6-methyl-4-pyrimidyl ) thiophosphate, 1,3-bis (carbamoylthio) -2- (N, N-diinethylaniino) propane hydrochloride, 3,4-dimethylphenyl-N-methylcarbamate, 1-naphthyl-If-methylcarbamate, 2-chloro- 4,6-bis- (ethylamino) -S-triazine, 2,4-dichloropheneoxyacetic acid, its salts and esters, 2-methyl-4-chlorophenoxyacetic acid and its salts and esters, 2,4-dichlorophenyl-4-nitrophenyl ether , N- (3,4-dichlorophen yl) propionamide, 3- (3 ', 4'-dichlorophenyl) -1,1-diraethylurea, 4-chlorobenzyl-N, N-dimethylthiol carbamate,

^ 09820/1155

1,1 '-Dimethyl-4,4' - "bipyridiuHidicliloria", 2,4,6-.trichlorophenyl-4 'nitrophenyl ether, N' - (2-methyl-4-chlorophenyi) -N, N-dimethylformaraidin, N _f ND ± allyl ~ 2-chloroacetainide, -ethyl- (or cyclohexyl) -A- (2,4-diphlorphenoxy) acrylate, Sn-heptyl-S «- (p-tert-butylbenzyl) -N- (5'- pyridyl) imidodithiocarbonate or Sn-butyl-S'-Cp-tert, - ■ butylbenzyl) -N- (3-pyridyl) -imidodithiocarbonate. The fungicidal compositions of the invention can also contain one or more substances with "bactericidal, insular, nematocidal, acaricidal or herbicidal activity, fertilizers, soil conditioners or plant growth substances....

Typical examples of fungicides according to the invention are:

(a) Dusts obtained by dispersing at least one compound of the general formula I in a concentration of 0.1 to 30 percent by weight in an inert carrier, for example Talc, diatomaceous earth, wood flour or clay .

(b) wettable powder obtained by dispersing at least one 3,5-dichlorophenyl compound of the general formula I in a concentration of 0.2 to 80 percent by weight in one inert, adsorbing carrier, e.g. diet clay, together with a wetting and / or dispersing agent, such as an alkali metal salt - a long chain aliphatic sulfate, a partially neutralized sulfuric acid derivative of either a petroleum component or a naturally occurring one GIy c er ids, or a Konüensationsprodukt of an alkylene oxide with an organic acid are obtained,

c) emulsifiable concentrates, which by dispersing at least a 3,5-dichlorophenyl compound of the general formula ^ I in a concentration of 1 to 50% by weight in one , organic solvents such as dimethyl sulfoxide, along with a breaking and / or dispersing agent such as an alkali metal salt of a long chain aliphatic sulfate j

• 409 82 0/11 5 S - ■ " ^r :; · ^

a partially neutralized sulfuric acid derivative of either a petroleum component or a naturally occurring one Glyceride, or a condensation product of an alkylene oxide obtained with an organic acid, and (d) fungicidal agents containing the 3,5-dichlorophenyl compound (s) of general formula I formulated in a manner that is customary for fungicidal incense agents is.

The comparative tests show the superiority of the fungicidal agents according to the invention.

In the following experiments, the compounds listed in the table below are used for comparison purposes, Compounds numbers 1 to 9 in US Pat. No. 3,215,597 and compounds numbers 8 to 16 in US Pat. No. 3,261,845 be * - are written.

Connection no.

structure

COOH

CONII

f ^H

-Cl

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Connection no.

structure

Vj / ^ CONH-

.Cl

\ | x ^ -CONH

CO. CO

COOH

Cl

CONH-V 7-Cl

CO

CO

co

co

Cl

• ci

Cl

* Cl-

8 2 0/1155

Connection no .

13 14 15 16

- 10 -

structure

Cl

CO _n CO

CO. CO

CO. CO

"N

Cl

Oil

Cl

HO.

"K

"NO,

Cl

CO,

\ J

CO

CO.

CO

Cl

Cl

Cl

"N

Cl

Cl

409820 / 1.155

Attempt a

A dust containing 3 percent by weight of the test compound, is used in an amount of 3 kg. of the dust per 10 ares on rice plants planted in pots with a diameter of 9 cm.

etv / a
that have been pulled to a height of Y "60 cm.

After 1 day the leaf sheath is covered with a 1 / Iycei disc

Pellicularia sasakii (diameter 5 mm) infected as an inoculation preparation. After 5 days the leaf sheath is infested observed, and the extent of the infestation is determined by the following equation calculated: .._ ■ · .-

Infestation index χ number _{of stems Total number of} stems, χ 3

whereby the infestation index is determined according to the following characteristics:

Bef al! Are ex Bef allszjistand ,

0 No infected areas on the leaf sheath

1 Infested, speckle-like areas

2 infestation spots less than 3 cm in size

3 infestation spots of at least 3 cm in size

The results are compiled in Table I. From Table I it can be seen that the 3-5 dichlorophenyl compound (I a _?: R = H) has a considerably greater fungicidal activity than the analogous compounds, for example the corresponding monochlorinated compounds »

409820/1: 155

Test connection

Table I.

Quantity (as 3
Dust (kg / 10 Ar)

Degree of infestation

invention la • ₂ : R = H 3 link comparison No. 3 3 link No. 4th 3 link No. 5 3 link untreated

0.0

100.0

100.0

77.8

100.0

Try'hB '

A test compound in the form of a wettable powder, after diluting with water in an amount of 10 ml of the dilution Applied per pot to kidney bean seedlings that are in pots of 9 cm in diameter and grown to the two-leaf stage. After 4 hours the leaves will be covered with a mycelium disc infected by Sclerotinia sclerotioruia (diameter 5 mm) as an inoculum. The infected leaf areas are Observed 4 days later. The extent of the damage is determined using the following equation:

Sehädieururserad - ^ infestation index χ number of leaves) bcnaaigungsgraü - _{total number of} leaves

whereby the infestation index is determined according to the following characteristics:

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.- 13 -

Infestation index Infested areas --... "

0 None ■ ■.

1 - Just around the vaccinated sites

2 Up to 1/5 of the total area of the inoculated leaf

3 More than 1/5 and up to 2/5 of the total area of the inoculated leaf

4 More than 2/5 and up to 3/5 of the total area of the inoculated leaf

5 More than 3/5 'of the total area of the inoculated leaf

The results are shown in Table TI. From table

- ■ -.- ■ '
le II it follows, that. the 3, 5-dichloropheny! compounds (I ' a ,; R. = H), (I a ₂ : R = H), (I a ₂ : R ^ Na) and (I b ^) are considerable have greater fungicidal activity than the analogous compounds, for example the corresponding monochlorinated compounds.

4 0 9 8 2 0/1155

-H-

^a 1 T a at le II Degree of damage Test connection a ₂ concentration ^a 2 (ppm) invention v 0.2 Connection (I. : R = H) 100 0.0 Connection '(I. 1 : R = H) 100 0.0 Connection (I. 2 : R = N / A). 100 0.0 Connection (I. 3 100 comparison 4th 5.0 Connection no. 5 100 5.0 Connection no. 6th 100 5.0 Connection no. 7th 100 5.0 Connection no. 100 3.0 Connection no. 100 3.8 Connection no. 100 5.0 Connection no. 100 commercially available fungicide 2.4 *)
"Resisan"' 100 5.0 Untreated -

*) 2,6-dichloro-4-nitroaniline as active ingredient

Try .

A test compound in the form of a wettable powder is used according to when diluting with water in an amount of 10 ml of the dilution per pot applied to bean seeds in pots of Planted 15 cm in diameter and up to the third three-leaf instar have been drawn. After four hours the leaves will be with an Ijycel disc of Sclerotinia sclerotiorum (through

l_messer 5 mm) infected as a vaccine preparation. The infected areas

A09820 / 1155

the leaves are observed 3 days later. The size of the infected spots is measured, the extent of the damage determined according to the following equation:

ο -u · - j-- -n 2 £ (Befal] are ^; ex χ number of sheets )

Degree of damage =

where the infestation index is determined based on the following characteristics:

Affected index of those affected · :, surfaces

0 None.

1 Up to Ί / 5 of the total area of the inoculated leaf

2. More than 1/5 and up to 2/5 of the total area of the.

inoculated leaf

3 ._ - ■ More than 2/5 and up to 3/5 of the total area of the

• inoculated leaf

4 More than 3/5 u: id up to 4/5 of the total area of the inoculated leaf

5 More than 4/5 of the total area of the gapped leaf

The degree of disease prevention is given by the following equation certainly:

Degree of sickness prevention =

(Size of the disease spots in _ (size of the disease spots of the untreated parcel. & Lle) - / ..--. In the treated parcel) (size of the disease spots in the untreated parcel

The results are shown in Table III. It follows from Table III that the 3 »5-DieM.orph.enyl compound 'I b _?

4 09.820 / 1 155,

a greater fungicidal activity than the analogous compounds, • for example the corresponding monochlorinated, dichlorinated, trichlorinated and dinitrated compounds.

Test connection

Tabel

III

concentration

(ppm) second sheet

third sheet

Damage Sick Damage Sickness- degree of clarity before-. degree of prevention

invention
Connection I bp

comparison
Compound No. 8 Compound No. 9 Compound No. 10 Compound No. 11 Compound No. 12 Compound No. 13 Compound No. 14 Compound No. 15 Compound No. 16 Untreated

500
100. 0.0
• ο, ο 500
100 4.9 500
100. 1.3
4.6 500
100 vjivji
OO 500
100 5.0
5.0 500
100 4.9
5.0 500
100 4.8
5.0 500
100 4.7
5.0 500
100 4.9
5.0 500
100 4.9
5.0

100
100

2
O

74
8th

0
0

0
0

2
0

4th
0

6th
Q

2
0

2
0

5.0 0.0 0.0

4.9 5.0

1.9 4.9

5.0 ■ 5.0

5.0 5.0

5.0 5.0

4.9 5.0

4.7 5.0

5.0 5.0

4.9 5.0

5.0

100 100

2 O

62 2

0 0

0 O

0 0

2 0

6 0

0 0

2 0

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V e rse u c h D

_ - ■ ■ "" diameter

Firebeans collections planted in pots of 9 cm / and up to first three-leaf stage (5 pots per Parz-el-Ie) are exposed to the smoke or steam of the test compound, the smoke or vapors by means of a heatable smoking device be generated. The fumigation takes place for 15 hours in a space that is closed off by vinyl foils; then the vinyl fo: l: leii are removed. Also be the plants, as described above, a foliar treatment with a 100-fold dilution of a 30% wettable powder of the test compound in an amount of 100 liters of the dilution subject per 10 ares. Seventeen hours after each

• "" treatments will be the top and the bottom of the leaves with a mycelial disc of Sclerotinia sclerotiorum infected as a vaccine preparation. The infested area of the Leaves are observed 4 days later. The extent of the damage is determined by the following equation:

", ..-..., ^ (infestation index χ number of leaves) Degree of damage =

The infestation index is determined according to the following characteristics

4 0 9 8 2 0/1155.

- 1Ö -

Bef al! Are ex-infected areas

O none

1. · Only around the vaccinated areas

2 bio to 1/5 of the total area of the vaccinated. Sheet

3 More than 1/5 and "bic to 2/5 of the G-e including the area of the inoculated leaf

4 More than 2/5 and up to 3/5 of the total area of the inoculated leaf

5. More than 3/5 of the total area of the inoculated leaf

The results are shown in Table IV. From table · -. It emerges from IV that the 3,5-dichlorophenyl compounds (I a ₂ : R = H), (IL) and (I bj have excellent fungicidal activity, and not only when they are used in the form of a wettable powder but also when used as a fumigant.

409820/1155

plot

Table IV Test Compound Amount

Degree of damage

link * 500 mg / m vaccinated
on the
Top vaccinated
on the
Under
page Incense (I a ₂ ί R = H) 100 mg / m he, o 0.0 25th mg / m 0.0 0.3- link , 100 L / 10 a ^; 0 * 0 0.8 leaves (I a ₂ : R = H) 0.0 0.0 link 500 mg / m ³ Incense (II) ₁ ) 100 mg / m ³ 0.0 • 0.0 25th mg / m ³ 0.0 0.0 link 100 L / 10 a *) 0.0 0.5 Leaves , (ι ^ ₁ ) 0.0 0.0 "Link 500 mg / m_ Incense (Ib ₂ ) ■ 100 mg / m 0.0 0.0 25th mg / m ³ 0.0 0.4- link 100 L / 10 "a * ^ 0.0 1.0 leaves 0.0 0.0

Untreated -

5.0

5.0

*) as a 1000-fold dilution of the 30 percent wettable Powder

Try

Cucumber seedlings are grown in pots with a diameter of 9 cm, and when they have reached the first trifoliate stage, the leaf is trimmed. A test compound in the form of a wettable After dilution with water, powder is applied to the

- 409820/115 5

Seed cotyledon of plants in an amount of 10 ml dilution applied per pot. After four hours, the leaves are covered with pieces of potato juice agar from Botrytis cinerea (diameter 5 mm) infected. The affected areas of the leaves become four Observed days later, the size of the disease spots being measured. The extent of the damage and the degree of disease prevention are determined according to experiment C.

The results are shown in Table V. Table V shows that the 3> 5-dichlorophenyl compounds (I b _? ) Have a considerably greater fungicidal activity than the analogous compounds, such as the corresponding mono-chlorinated, dichlorinated, trichlorinated or dinitrated compounds.

409820 / 1-155

ΐ est connection

. - 21 -

Table V
Concentration damage (ppm) degree of damage

Kxankhe its prevention (fo)

invention (I. 8th 200 0.0 100 link 9 comparison No. 10 200 5.0 ⁰ Link No. 11 200 3.4 • 32 link No. 12th 200 4.9 ■ .2 link No. 13th 200 5.0 O link No. 14th 200 4.7 ■ 6
V. link No. 15th 200 4.9 i
2 link No. 16 200 4.8 - ■ 4 link No. 200 '5.0 O link No. 200 5.0-- * O link - 5.0 Untreated

V e r s u c h F

Cucumber seedlings are grown in pots with a diameter of 9 cm, and when the single leaf stage is reached, the leaf is trimmed. A test compound in the form of a wettable powder is, after dilution with water, on the seed leaf of the Plants applied in an amount of 10 "ml of the dilution per pot ·. After 4 hours the leaves will be covered with a mycelium disc of Botrytis cinerea (5 ram diameter) as an inoculation preparation infected. The affected areas of the leaves become five Days later observed the degree of visual damage is as in the experiment D calculates «, - '·

409820/1155

Γ "_ PP - ~ Ι

The results are shown in Table VI. Table VI shows that the 3,5-dichlorophenyl compounds (I a ₁ : R = H), (I a _?: R = * H), (I a ~: R = Na) and (I b ..) have a significant impact have greater fungicidal activity than the analogous compounds, such as the corresponding monochlorinated compounds.

Tab 1 Ί e VI
Test connection 'Concentration (ppm) Degree of damage

0.1 0.0 0.0 0.0

invention (I. a _T : R = H) 200 link (I. a ₂ : R = H) 200 link (I. a ₂ : R = Na) 200 link (I. V 200 link comparison No. 1 200 link No. 2 200 link No. 3 200 link No. 4th 200 link No. 5 200 link No. 6th 200 link No. 7th 200 Link. Commercially available fungicide *)
"Triazine"' 200 Untreated

4.5 5.0 5.0 5.0 3.1 3.7 5.0

1.4 5.0

*) 2,4-dichloro-6- (2-chloroaniline) -S-triazine as active ingredient

V e r s u c h G

Field baths are first given in pots with a diameter of 9 cm. Then 10 ml of soil are inoculated with Pelljcularia filamentosa ^

is distributed over the surface. After a test connection has been diluted in the form of an emulsifiable concentrate with water to a concentration of 50,000 ppm, the thinning poured into the pots in the amount of 15 ml per pot. After four hours, 10 cucumber seeds are sown. Five days later the infestation of the growing seedlings is observed. The percentage status is calculated using the following equation:

Number of healthy · seedlings in the treated plot Number of keiinten- plant! in the untreated parcel

Percentage level = _{1 Q}

■ Number of different balance sheets

The results are shown in Table VII. Table VII shows that the 3,5-dichlorophenyl compounds (I a _2. "R = H) and (I a ₂ : R = Na) have a considerably greater fungicidal activity than the analogous compounds, such as the corresponding monochlorinated compounds.

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2 T a b e "cn - 2354873 J . 0 2 lie VII 0 Test connection * concentration percentage status O 3 (ppm) (*) invention 4th : R ■ = H) 0 Connection (Ia 5 : R = Na) 500 100 100 Connection (I a 500 100 comparison Connection no. 500 -Connection no. 500 Connection no. 500 - untreated vaccinated - not vaccinated _

attempt

PI

First of all, arable soil is placed in pots with a diameter of 9 cm.

F. raphanl then 10 ml of soil inoculated with Pusariunj οxysporumYg are spread over the surface. A test compound in the form of an digestible concentrate is diluted with water to a concentration of 500 ppm, and the dilution is poured into the pot in an amount of 15 ml per pot. After four hours, 20 radish seeds are sown. The infestation status of the grown seedlings is observed three weeks later. The percentage level is calculated as in Experiment G.

The results are shown in Table VIII. Table VIII shows that the 3> 5-dichlorophenyl compounds (I a ₂ : R = H) and (I a ": R = Na) have a considerably greater fungicidal activity than the analogous compounds, such as the corresponding ones

409820/1155

monochlorinated compounds, possess,

Test connection

T a b e 1 1 e VIII '

Concentration percentage level (ppm)

invention 500 100 Connection (I a _g : R = H) .500 1.00 Connection (Isu: R = Na) comparison 500 0 Connection No. 3 500 0
I. Connection No. 4 500. t
35 Compound No. 5 commercially available fungicide 500 45. "Tachigars" '· Untreated - 0 vaccinated 100 not vaccinated

*) 3-Hydroxy-5-methylisoxazole as active ingredient

The results of the above experiments produced that is the _p

phenyl.

the fungicidal agents of the invention containing 3,5-dichloro compounds of the general formula I are valuable "services in combating plant diseases, such as Sclerotinia red ₉ Rhizoctonia red and Botrytis" gray mold ⁿ "in vegetables and crops _s rice brandy brown leaf spots or sheaths mildew ( "sheath blight") .leisten on rice plants · _{9 o} 3 _S 5-Dichlorphenylverbindungen of the general formula I can be applied as such auck _o for practical. reasons, however, it .werden -in general in'Form fungicidor means in communication with belie "bi = _r

409820/1155

gen, inert carriers used in agriculture • or diluents, as well as any surface-active substances or wetting agents applied. The concentration of the compounds of general formula I in the fungicidal agents

approximately
can be 0.1 to 90 percent by weight.

The examples illustrate the invention. All parts and percentages relate to the face.

B is ρ ie 1 1
Manufacture of wettable powders:

(A) 50 parts of N- (3 _'f 5 ^l -Dichlorphenyl) norbornane-2,3-dicarboximide, melting at 171.0 to 172.5 ⁰ C (compound II) _1), 5 parts of a wetting agent (Alkylbenzolsülfonat) and 45 parts of DiatoEeenarde are broken or ground and mixed well. This gives a wettable powder with an active ingredient content of 50 fo. For use, the wettable powder is diluted with water. - ''

(B) According to Example 1 (A), a wettable powder is made using the sodium salt of 3- (3 ' ₉ 5' -Dichlorophenylcarba.- ■ = 7 ~ oxabicyclo- (2j2 ^ 1) -heptane-2-carboxylic acid from F.

G (decomp.) (Compound I 'a ~: R = Na) instead of the compound I b. manufactured",

It becomes a wettable powder according to example. 1 (A) using M = {3 ^s _ΰ 5 ^s —Dienlorophenyl) -7-oxabicyeXo— (2 _d 2 _s 1) ■ =

from Fo 154 Ms 155 ⁰ O {

ai & telle && z ~ Ymfblrxtting I b, ·, made _o "

ί ι ί b 5

Example 2
Production of dusts:

(A) 3 parts of 3- (3 *, 5 ^I -Dichlorphehylcarbamoyl) - norbornane-2-carboxylic acid, melting at 151.5 to 153> 5 ⁰ C (compound I a \, R = H) and 97 parts of clay are broken or ground and mixed well so that a dust with an active ingredient content of 3 % is obtained. This dust can be used as it is. · "·

(B) A dusting agent according to Example 2 (A) using 3- (3 ', S'-dichlorophenylcarbamoyl) -7-oxabicyclo- (2,2,1) -heptane-2-carboxylic acid from P. I83 to "184 ° C (compound I a ₂ : R = H) instead of the compound Ia. (R = H).

(C) A dust according to Example .2 (A) is used the compound I bp instead of the compound I a. (R = H) manufactured. , ·

Example 3
Production of emulsifiable concentrates:

(A) 10 parts of compound I "b ^, 70 parts of dimethylformamide,

10 parts of toluene and 10 parts of an emulsifier (polyoxyethylene dodecylphenol ether) are mixed thoroughly to form an emulsifiable concentrate which contains 10 % of the active ingredient. This emulsifiable concentrate is before application. diluted with water.

(B) An emulsifiable concentrate according to Example 3 (A) using the compound 1 a ₂ (R - H) instead of the compound I b. manufactured.·

409 8 20/1 1 5 5 - ¹

(G) An emulsifiable concentrate according to Example 3 (A) using the compound .1 bp instead of the compound I b | manufactured.

Example 4
Manufacture of incense:

(A) 90 parts of the compound I b., 3 parts of a nitrite, 2 parts of wood flour and 5 parts of diatomaceous earth are pulverized and mixed thoroughly, producing a fumigant which contains 90 % of the active ingredient. The smoking agent is used by smoking by means of a heatable smoking device.

(B) To produce a fumigant according to Example 4 (A) ″, the compound I a ₂ (R = H) is used instead of the compound I b ₁ .

(C) A smoking composition according to Example 4 (A) is prepared using the compound I b ₂ instead of the compound I b ₁ .

Example 5 Production of complex, wettable powders:

(A) 40 parts of the compound I ^, 10 parts of Sn-butyl-S »- (p-tert-butylbenzyl) -N- (3-pyridyl) dithiocarbonate, 45 parts of diatomite and 5 parts of a wetting agent (calcium lignin sulfonate ) are pulverized and mixed thoroughly. This gives a wettable powder containing 50 fi V / he active ingredient contained.

The complex wettable powder is before application with Water diluted.

(B) A complex wettable powder according to Example 5 is obtained

• (A) using the compound I bp instead of the

409820/1155 ^J.

bond I b- established. ■ _ ·. '"■"

(C) 4 parts of the compound I a ^ (R = H), 60 parts of manganese-äthylenbis- (thiocar "bamate), 30 parts of diatomaceous earth and 6 parts of a wetting agent (an alkylbenzenesulfonate) are pulverized and mixed thoroughly, resulting in a complex Powder that contains 64 "$> of active ingredients. The complex wettable powder is diluted with water before use.

(D) A complex wettable powder is produced according to Example 5 (C) using the compound I a ₁ (R = H) instead of the compound Ϊ a ₂ (R = H). . "■ ',

409820/1155

Claims (4)

Patent claims: 1. Fungicidal agents, consisting of 0.1 to 90 percent by weight of at least one 3 »5-dichlorophenyl compound of the general Formula I. , 2 _Λ / Cl (D in which A denotes a methylene group or an oxygen atom, 1 2 R is a hydrogen atom and R is a hydroxyl group or the remainder OHe, where Me is an alkali metal, represents, or R and ρ
R together denote a bond with the formation of an imide ring, as well as customary carriers, diluents and other auxiliaries. 2. Use of the 3,5-dichlorophenyl compounds of the general Formula I for combating fungi. 3. Embodiment according to claim 2, characterized in that they are phytopathogenic fungi of the genus Sclerotinia. 4. Embodiment according to claim 2, characterized in that it is phytοpathogenic fungi of the genus Botrytis. 409820/1155