IL37109A - Fungicidal composition containing 1,3-bis(-3-alkoxycarbonyl-2-thioureido)benzene and another ingredient - Google Patents

Description

37109/2 -2-7 i: i7'0|7w K-3)-D':--i,3 o'^'Dan mnos ' oii? o»v¾on FUNGICIDAL COMPOSITION CONTAINING 1.3-BIS- (-3-ALKOXYCARBONYL-2-THIOUREIDO) BENZENE AND ANOTHER INGREDIENT the weight ratio of the two components being between 1:20 and 20: 1.

BACKGROUND OF THE INVENTION It is known that the fight against cryptogamic disease harmful to cultivated plants holds special importance because such diseases can cause serious harm to agricultural cultivations and greatly impair the economic value of the crop.

When there are used in agriculture chemical products having an anticryptogarnic or fungicidal action it is therefore necessary to obtain effective results, in order to be able to increase commercially the agricultural production of high quality.

The object of the present invention is to provide improved fungicidal compositions for use in agriculture.

SUMMARY OF THE INVENTION The compositions in accordance with the invention comprise a mixture of at least one compound (i) of the formult in which R is an alkyl group with from 1 to 4. carbon atoms, with at least one compound (il) selected from: dodecyl guanidine acetate (Dodina) 1 , -dithiqanthraquinone ('Carbon!trile (Dithianon) trichloromethylthiotetrahydrophthalimide (Captan) trichloromethylthiophthalimide (Phaltan) zinc ethylenebisdithiocarbamate (Zineb) manganese ethylenebisdithiocarbamate (Maneb) t with the addition of activants such as surfactants, suspending! agents, adhesive agents, or stabilizing agents and even with the possible addition of fertilizers or trace elements both for application to the vegetation and to the soil.

The potentiating effect observed in the fungicidal mixtures of the invention, besides being useful against various cryptogamic diseases, is particularly evident in the use of the mixtures themselves in the fight against apple scab (Venturia inae'qualis or Fusicladium dentriticum) or agaiji pear scab ( Fusicladium pyrinum or Venturia p.yrina) and above all in the first phase of the vegetative development of fruit| i bearing plants.

The production of the mixture in accordance with the invention is carried out in accordance with a process which comprises mechanical mixing of the individual preselected components and adding to these surface active, suspending, dispersing, stabilizing and activating agents and inert and possibly fertilizing substances,- mixing and then grinding the| whole until a fineness of the particles less than 50 microns is obtained.

. There will now be quoted hereinunder some examples to illustrate the invention in greater detail. The first two of these relate to the formulation of compositions in accordance with the invention, the others to some of its practical appli cations. However, . these do not in any way constitute a limitation of the invention.

EXAMPLE I- . kg of 1,2 bis-( 3-methoxycarboriyl-2-thioureido )-ben zene, 30 kg of dodecyl guanidine acetate, '5 kg of · ethoxylated stearic acid amides, 2 kg of sodium dibutylnaphthalenesulpho nate, .5 kg' of Sodium ligninsulphonate and 2-8 kg of fine silic powder, are taken and mixed accurately. The whole is crushed finely in a powder mill until particles of diameter less than 50 microns are obtained.

EXAMPLE II kg of 1,2 bis-( 3-ethoxycarbonyl-2-thiou'reido )-benze ne, 50 kg of the complex salt of zinc and dimethyl- and ethy_l enebis-dithiocarbamic acids (Zireb), 5 kg- of sodium dibutyl-naphthalenesulphonate, 2 kg of the sodium salt of. the forma_l' dehyde condensate of naphthalenesulphonip acid,' 5 kg sodium ligninsulphonate , and 23 kg of fine silica powder are taken.

The whole is mixed in a powder mixer and crushed in a mill to obtain a powder with particles of fineness less than 50 microns.

One obtains a powder which can be employed both for spraying on the vegetation and for sprinkling as it is on the ground.

EXAMPLE III To combat apple scab (Venturia inaequalis or Fusicla-dium dentriticum) apple-trees of the variety Red Delicious are sprayed by means of a pressure pump with aqueous suspensions of the fungicides listed below during the period of cryptogamic infection from the opening of the buds to the end of the primary infection, at weekly intervals, obtaining the results listed below, in which the efficiency is calculated as the reduction of the cryptogamic infection with regard to plants not treated with fungicides placed in the midst of plants sprinkled with anticryptogamics.

Fungicides used and dosage % efficiency against th 2 apple fruit scab ■ 1a) 1 ,.3-bis( 3-ethoxycarbonyl-2- thioureido ) -benzene 0.04% 50 2a) complex salt of zinc and dimethyl-and ethylenebisdithio- carbamic acids (Zireb) 0.08 .22 3a) 1 , 3-bis( 3-ethoxycarbonyl-2- thioureido )benzene 0.04% + complex s'alt' of zinc and 'dimethy-and ethylenebis-dithiocarbamic acids 0.08% 96 1b) 1 , 3-bis( 3-methoxycarbonyl-2-thioureido ) benzene 0.02% 2b) dodecyl guanidine acetate 0.02% 3b) 1 , 3-bis-( 3-methoxycarbonyl-2- thioureido ) -benzene 0.02% + dodecyl guanidine acetate 0.02% It will be observed that the fungicidal mixtures are. more effective than the sum of the efficiency; of the products used on their own at the same dosage.

With the use of the fungicidal mixtures of this invention there! are thus obtained results which are unexpectedly superior.

EXAMPLE IV Pear trees of the variety Passacrassana are sprayed at intervals of 6 days with aqueous mixtures containing the fungicides listed below, beginning the treatment with the opening of the buds.

At the end of the season of primary infection of pear scabs (Fusicladiun pyrinum or Venturia pyrina) the efficiency of the various products is noted in terms of the reduction in the infection on the fruits by comparison with untreated plants, obtaining the results quoted hereinunder: Fungicides- used and dosage % efficiency against x pear scabs 1a) 1 , 3-bis-( 3-ethoxycarbonyl-2- — : thioureido) -benzene 0.04% 41 2a) trichloromethylthio-tetra- • hydrophthalimide 0.05% 32 3a) , 3-bis-( 3-ethoxycarbonyl-2- . . ' . thioureido )-benzene 0.04% + · trichloromethylthiotetra- hydrophthalimide 0.05% 92 1b) 1 , 3-bis- ( 3-methoxycarbonyl-2- thioureido) -benzene 0.01 % 42 2b) dodecyl guanidine acetate 0.02% 36 3b) 1 , 3-bis-( 3-methoxycarbonyl-1-2- It will be observed · that the mixture of fungicides listed above have a far greater efficiency than the sum of th efficiencies of.' the fungicides used on .their own, thus demons trating an unexpected greater effectiveness. ' EXAMPLE V Aqueous suspensions of the fungicides listed below are sprayed on apple trees of the variety Imperatore, the treatments beginning with the opening of the buds and continuing every 5 days up to the end '.of the primary infection of apple scab ( Venturia inaequalis or Fusicladium dentriticum.) .At that time the efficiency of the various fungicidal mixtures is observed in terms of the reduction in the infection of scab with respect to plants of the same orchard left without treajt ment and there' are obtained the results quoted here.

Fungicidal compounds and dosage % efficiency apple scab 1a) 1 , 3-bis( 3-ethoxycarbonyl-2- thioureido )-benzene 0.04% 48 2a) zinc and manganese ethyiene- bisdi thiocarbamate 0.< 26 1 , 3-bis- ( 3-ethox'ycarbonyl-2 thioureido ) -benzene + zinc and manganese ethylenebisdi thiocarbamate 0.08% . 91 1b) 1 , 3-bis-( 3-methoxycarbonyl-2- / thioureido) benzene 0.015% 42 2b) trichloromethylthio-tetrahydro- phthalimide 0.05% '36. 3b) 1 , 3-bis-( 3-methoxycarbonyl-2- thioureido ) -benzene 0.015% + trichioromethylthio-tetrahydro- phthalimide 0.05% 96 The efficiency of the fungicides used in the mixtures is clearly higher than the sum of the efficiencies of the fungicides used on their own, thus demonstrating a potentiating effect of the mixtures of fungicides.

Claims (3)

1. WHAT WE CLAIM IS: 1 ) A fungicidal composition comprising a mixture of at least one compound (i) of the general formula: in which R is san alkyl group with 1 to carbon atoms, with a least one compound (il) selected from: dodecyl guanidine acetate (Dodina) 1 , -dithi$anthraquinone -^,(3-c¾.rbonitrile (Dithianon) trichloromethi-lthio - tetrahydrophthalimide (Captan) trichloromethylthio - phthalimide (Phaltan) zinc ethylenebisdithiocarbamate (Zineb) manganese ethylenebisdithiocarbamate (Maneb) manganese and zinc ethylenebisdithiocarbamate (Mancozeb) zinc propylenebisdi.thiocarbamate (Propineb) zinc ethylenebisdithiocarbamate/thiuram complex (Metiram)] tetramethylthiuram disulphide (TMTD) zinc dimethyldithiocarbamate (Ziram) iron dimethylthiocarbamate (Ferbam) . / complex salt of zinc and dimethyl- and ethylenebisdithio carbamic acids (Zireb).

2. ) A fungicidal composition according to Claim 1, in whji the ratio by weight of the component or -components I with the component or components II is between 1:20 and '20:1.

3. ) A composition according to Claim 2, in which the [said ratio is between 1:10 and 10:1. - ) A composition according to Claim 1, 2 or 3 additionc 1 comprising one or more surface active and/or suspending and/o dispersing and/or stabilizing. and/or activating agents and/or 5) A fungicidal compositioraccording to any of Clams 1 to 4 "comprising 1 , 3-bis-(3-ethoxycarbonyl-2-thioureido)-benzene and the complex salt of zinc and dimethyl- and ethyle nebis - dithiocarbamic acids. 6) A fungicidal composition according to any-, of Claims 1 to 4 comprising 1 , 3-bis-( 3-ethoxycarbonyl-2-thioureido)-benzene and dodecyl guanidine acetate. 7) A fungicidal composition according to any of Claims 1 to 4 comprising 1, 3-bis-( 3-ethoxycarbonyl-2-thioureido )ben zene and trichloromethylthio-tetrahydrophthalimide . 8) A fungicidal composition according to any of Claims 1 to 4 comprising 1 , 3-bis- ( 3-methoxycarbonyl-2-thioureido ) ben zene and the complex salt of zinc and dimethyl- and ethylene bis-dithiocarbamic acids. 9) A fungicidal composition according to any of Claims 1 to 4 comprising 1 , 3-bis- ( 3-methoxycarbonyl-2-thioureido ) ben zene and dodecyl guanidine acetate. 10) A fungicidal composition according to any of Claims 1 to 4 comprising 1 , 3-bis-( 3-methoxycarbonyl-2-thioureido )ben zene and trichloromethylthio-tetrahydrophthalimide. 11 ) Ά fungicidal composition substantially as described [with specific reference to any of Examples I to VI. .' 12) A process for producing fungicidal compositions according to any of the foregoing claims which comprises mech nically mixing the individual components I and II, optionally adding surface active, suspending, dispersing, stabilizing or activating agents and/or inert or fertilising substances, mix-} in and then grinding the whole to a. particle size' less than 50 microns. 13) A method of combatting cryptogamic infections in (plants by application thereto of a fungicidal composition, in accordance with any ,of Claims 1 .to 11. 14) A method according to Claim 13 when applied to appl trees or pear trees against infections of scab (Venturia inae