BE889317Q - NOVEL ARYLHYDRAZO-ALDOXIMES AND THEIR USE AS FUNGICIDES - Google Patents

Description

       

  "Aryihyàrazo-aldoxirnes new and their employment as

  
as fungicides "<EMI ID = 1.1>

AS FUNGICIDES

  
The present invention relates to the use as fungicides

  
 <EMI ID = 2.1>

  
they were only indicated as intermediaries for obtaining at. very composed.

  
The present invention relates to the use of arylhydrazo-aldoxime:
for their biological activity.

  
 <EMI ID = 3.1>

  
 <EMI ID = 4.1>

  
It also relates to new arylhydrazo-aldoximes and to their emp to fight against fungi and other fungi.

  
In fact, it has been found that the arylhydrazo-aldoximes of formula hinder

  

 <EMI ID = 5.1>


  
or their tautomers of formula:

  

 <EMI ID = 6.1>


  
in which:

  
X and Y are hydrogen atoms, halogens, alkyl radicals

  
 <EMI ID = 7.1>

  
 <EMI ID = 8.1>

  
R is a hydrogen atom, an alkyl radical comprising 1 to 5 atoms

  
carbon, a phenyl or substituted phenyl radical, <EMI ID = 9.1>

  
are active, whether as such or in the form of mineral or

  
 <EMI ID = 10.1>

  
treat (i.e. reduce) fungus infestations against beneficial plants, as well as immunize plants against the risk of infestations (as they avoid even when applied far from the point

  
 <EMI ID = 11.1>

  
 <EMI ID = 12.1>

  
The new arylhydrazo-aldoximes according to the invention are cited in the

  
 <EMI ID = 13.1>

  
known aldoximes whose activity has been tested (the bibliographic references relating to these known compounds are mentioned opposite said compounds).

  
The methods of preparation are those indicated in article b 1 &#65533; .C.

  
The arylhydrazo-aldoximes according to the present invention can be administered to plants as such or in the form of compositions prepared according to conventional techniques: they can be mixed with inert powders, such as, for example, kieselguhr, activated carbon, gypsum, urea, etc., au can be administered, if necessary, after addition to agents

  
 <EMI ID = 14.1>

  
They may also be dissolved dispersed or emulsified in water or be put into the form of solutions in organic solvents.

  
The activity of these compounds has been tested on various plant species

  
 <EMI ID = 15.1>

  
curative activity), then after (in order to determine preventive activity)

  
 <EMI ID = 16.1>

  
say plants using the fungicide agent partly in a position distant from the point of infestation (to determine immunizing activity).

  
 <EMI ID = 17.1>

  
reading of the following examples, given by way of illustration but not limitation; the first two of these examples relate to a method for preparing by synthesis the new compounds while the others relate to the activity

  
 <EMI ID = 18.1>

  
present invention.

  

 <EMI ID = 19.1>


  

 <EMI ID = 20.1>
 

  

 <EMI ID = 21.1>


  

 <EMI ID = 22.1>
 

  

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 <EMI ID = 24.1>
 

  
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 <EMI ID = 26.1>

  
 <EMI ID = 27.1>

  
 <EMI ID = 28.1>

  
trihydrate.

  
At the end of this addition, the mixture is stirred for 3 hours at

  
 <EMI ID = 29.1>

  
 <EMI ID = 30.1>

  
 <EMI ID = 31.1> <EMI ID = 32.1>

  
 <EMI ID = 33.1>

  
 <EMI ID = 34.1>

  
 <EMI ID = 35.1>

  
Upon completion of the reaction, the solvent is removed under reduced pressure

  
 <EMI ID = 36.1>

  
 <EMI ID = 37.1>

  
in the form of a white solid, having a melting point of the order of
124 [deg.] C (with decomposition).

  
EXAMPLE 2

  
 <EMI ID = 38.1>

  
 <EMI ID = 39.1>

  
 <EMI ID = 40.1>

  
 <EMI ID = 41.1>

  
The solid that forms is filtered; thus obtaining 75g of chlor-

  
 <EMI ID = 42.1>

  
decomposition.

  
EXAMPLE 3.

  
 <EMI ID = 43.1>

  
Vine leaves (cv. Dolcetto) grown in pots in an atmos-

  
 <EMI ID = 44.1> 4

  
 <EMI ID = 45.1>

  
 <EMI ID = 46.1>

  
 <EMI ID = 47.1>

  
The plants of each of the groups then undergo a treatment of ir ro -

  
 <EMI ID = 48.1>

  
 <EMI ID = 49.1>

  
after infestation.

  
At the end of the incubation period (7 days), eyesight is determined 4, according to an evaluation scale between 100 (healthy plants) and 0
(totally infested plants), the import-, that of infestation.

  
We observe the following results: <EMI ID = 50.1>

  

 <EMI ID = 51.1>


  
EXAMPLE 4 <EMI ID = 52.1>

  
 <EMI ID = 53.1>

  
Vine leaves (cv. Dolcetto) grown in pots in a conditioned atmosphere, are sprayed on their upper sides

  
 <EMI ID = 54.1>

  
products tested.

  
Plants are kept in a. = Conditioned atmosphere for

  
 <EMI ID = 55.1>

  
 <EMI ID = 56.1>

  
 <EMI ID = 57.1>

  
saturated with humidity, the plants are again placed in a conditioned atmosphere.

  
 <EMI ID = 58.1>

  
according to an evaluation scale between 100 (healthy plants) and 0
(totally infested plants), the importance of the infestation.

  
The following results are observed:

Tested product Dose 9 of active product Activity

  

 <EMI ID = 59.1>
 

  
EXAMPLE 5

  
 <EMI ID = 60.1>

  
 <EMI ID = 61.1>

  
Beet leaves (cv. KWS polybeta), grown in an atmos

  
 <EMI ID = 62.1>

  
 <EMI ID = 63.1>

  
 <EMI ID = 64.1>

  
 <EMI ID = 65.1>

  
 <EMI ID = 66.1>

  
At the end of the incubation period (20 days), it is determined by sight, according to an evaluation scale of between 100 (healthy plants) and 0

  
The following results are observed:

Product tested Dose%, of active product Activity

  

 <EMI ID = 67.1>


  
EXAMPLE 6

  
Immunizing activity against Cercospora beet

  
 <EMI ID = 68.1>

  
Beet leaves (cv. KWS polybeta), grown in pots in a conditioned atmosphere, are sprayed on their

  
 <EMI ID = 69.1>

  
of the product tested.

  
The plants are then kept in a conditioned atmosphere during

  
 <EMI ID = 70.1>

  
 <EMI ID = 71.1>

  
 <EMI ID = 72.1>

  
atmosphere saturated with humidity, the plants are replaced in a conditioned atmosphere.

  
. At the end of the incubation period (20 days), it is determined by sight, according to an evaluation scale of between 100 (healthy plants) and 0
(totally infested plants), the importance of the infestation.

  
 <EMI ID = 73.1>

  
 <EMI ID = 74.1>

  

 <EMI ID = 75.1>


  
EXAMPLE 7

  
Curative activity against cucumber powdery mildew

  
 <EMI ID = 76.1>

  
Cucumber leaves (cv. Marketer) grown in pots in a conditioned atmosphere, are subjected to an irrigation of a suspension

  
 <EMI ID = 77.1>

  
After 24 hours, the said leaves are treated by irrigation on their

  
 <EMI ID = 78.1>

  
At the end of the incubation period (8 days), eyesight is determined 2, according to a scale of evaluation between 100 (healthy plants) and, 0
(totally infested plants), the importance of the infestation.

  
The following results are observed:

Product tested Dose%, of active drug Activity

  

 <EMI ID = 79.1>


  
EXAMPLE 8

  
 <EMI ID = 80.1>

  
 <EMI ID = 81.1>

  
Cucumber leaves (cv. M &#65533; rketer) grown in pots in a conditioned atmosphere, are subjected to irrigation, on their undersides

  
 <EMI ID = 82.1>

  
product tested. The plants are then kept in a conditioned atmosphere for 6 days. On the 7th day the leaves are subjected to an irro'ration on their upper faces with a solution of conids Sphaerotheca fuliginea (200,000 conids per cm <3>; after the plants are replaced in a conditioned atnosphere.

  
 <EMI ID = 83.1>

  
 <EMI ID = 84.1>

  
(plants, fully infested; the extent of the infestation, We note the following results: '

  
Tested product Dose [pound] of active product Activity

  

 <EMI ID = 85.1>


  
EXAMPLE 9

  
Curative activity against bean rust

  
 <EMI ID = 86.1>

  
Bean leaves (Borlotto di Vigevano) grown in pots in a conditioned atmosphere, are subjected to an irrigation on their

  
 <EMI ID = 87.1>

  
 <EMI ID = 88.1>

  
in an atmosphere saturated with humidity, said sheets are treated

  
 <EMI ID = 89.1>

  
 <EMI ID = 90.1>

  
At the end of the incubation period (14 days), it is determined by sight, according to a rating scale of between 100 (healthy plants) and 0

  
 <EMI ID = 91.1>

  
The following results are observed:

  
 <EMI ID = 92.1>

  

 <EMI ID = 93.1>


  
EXAMPLE 10
- Immunizing activity against bean rust <EMI ID = 94.1>

  
Bean leaves (cv. Borlotto di Vigevano) cultivated in pots in a conditioned atmosphere, smelled treated by irrigation on their

  
 <EMI ID = 95.1>

  
lume) of the product tested.

  
 <EMI ID = 96.1> <EMI ID = 97.1>

  
 <EMI ID = 98.1>

  
an atmosphere saturated with humidity, the plants are replaced in a conditioned atmosphere.

  
At the end of the incubation period (14 days), it is determined by sight, according to an evaluation scale between 100 (healthy plants) and 0
(totally infested plants), the importance of the infestation.

  
The following results are noted: - ', ..

  
Product tested Dose &#65533; of active product Activity

  

 <EMI ID = 99.1>


  
Of course, the present invention is in no way limited to the examples and modes of implementation described above; she is likely to

  
 <EMI ID = 100.1>

  
tion and without departing from the spirit of the invention.

  
 <EMI ID = 101.1>

  
 <EMI ID = 102.1>

  
 <EMI ID = 103.1>

  
be these Infestations, characterized in that they contain, as

  
as active ingredient, one or more arylhydrazo-aldoximes as such or

  
in the form of, organic or mineral salts having the general formula:

  

 <EMI ID = 104.1>


  
or consisting of its tautomer formula, formulas in which:

  
X and Y are hydrogen, halogen or alkyl radicals

  
 <EMI ID = 105.1>

  
R is a hydrogen atom, an alkyl radical comprising 1 1 5 carbon atoms, phenyl or substituted phenyl.

  
2.- Method to fight against infestations caused by cham-

  
 <EMI ID = 106.1>

  
immunize these plants against infestations, characterized in that the

  
 <EMI ID = 107.1>

  
 <EMI ID = 108.1>


    

Claims (1)

containing them according to claim 1, the quantity of fungicidal agent being <EMI ID = 109.1> 3.- As a new industrial product: <EMI ID = 110.1>   <EMI ID = 111.1> <EMI ID = 112.1> 44.- As a new industrial product:  <EMI ID = 113.1> 45.- As a new industrial product: <EMI ID = 114.1> 48.- As a new industrial product:  <EMI ID = 115.1>