FR2513997A1 - SUBSTITUTED N- (1-TRIAZOLE- (1) -YL-2,2,2-TRICHLORETHYL) -CARBOXAMIDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND OIDIUM COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENTS - Google Patents

Abstract

THE INVENTION CONCERNS DERIVATIVES OF THE TYPE N-1-TRIAZOLE- (1) -YL-2,2,2-TRICHLOROETHYL-CARBOXAMIDE SUBSTITUTE, A PROCESS FOR THEIR PREPARATION AND A COMPOSITION AGAINST OIDIUM CONTAINING THEM. THE COMPOUNDS OF THE INVENTION MEET THE GENERAL FORMULA: (CF DRAWING IN BOPI) IN WHICH R REPRESENTS A HYDROGEN ATOM OR A RADICAL METHYL, ETHYL, 2-TRIFLUOROMETHYLPHENYL, 2-HYDROXYPHENYL, 2-ACETROXYPHENYLE, 2-ACETROPHENYLE, 4-PHENOPETOX -PHYL 4-TERT-BUTYLPHENYL, 2-CHLORO-4-NITROPHENYL OR BENZYL OR RADICAL: (CF DRAWING IN BOPI) IN WHICH R AND R ARE SIMILAR OR DIFFERENT AND RESPECTIVELY REPRESENT A HYDROGEN, FLOROR, CHLORINE, CHLORINE ATOM BROMINE OR IODINE OR A RADICAL METHYL OR METHOXY. APPLICATION TO POWDERY COMPOSITIONS FOR THE CONTROL OF OIDIUM.

Description

N-1-triazole- (1) -yl-2,2,2-trichloroethyll-1 derivatives

  substituted carboxamide, process for their preparation and

  against oidium containing them as active ingredients. The present invention relates to substituted N-1-triazole- (1) -yl-2,2,2-trichloroethyl-carboxamide derivatives and oidium compositions containing them.

as active ingredients.

  More particularly, the invention relates to derivatives

  N-1 11-triazole- (1) -yl-2,2,2-trichloroethyll-car-

  substituted boxamide represented by the general formula (I)

R C NH CH -N (I)

  CC 13 wherein R represents a hydrogen atom, or a

  radical methyl, ethyl, 2-trifluoromethylphenyl, 2-hydroxy

  xyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-

  butylphenyl, 2-chloro-4-nitrophenyl, benzyl or a

formula cal

R

> (II)

R 2

  in which R 1 and R 2 are the same or different and

  respectively present a hydrogen, fluorine, chlorine, bromine or iodine atom or a methyl or

  methoxy, and an agent against oidium containing such a compound

  layer of general formula (I) as active ingredient.

  Many compounds having a triazole group as a substituent are known to date, useful as agents for

  fight against plant diseases, and some of

  they have been patented (see, for example, requests for

  Japanese Patent Nos. 52-148073 (1977) and 55-17390 (1980).

  Moreover, although it is known that N-type derivatives

  (Azolylhaloalkyl) carboxamide, for example the N- (1-imidazolyl-2,2,2-trichloroethyl) -carboxamide derivatives (see Chemical Abstract, 83, 114405 e (1975)), are

  active against eumycetes, it is not indi-

  In the literature, they behave as fungicides useful in agriculture or horticulture. Although described in Japanese Patent Application No. 52-17473 (1977) (see Chemical Abstract, 87, 152221).

  (1977)) that derivatives of N- (1-azolyl-2,2,3-trichloro

  propyl) -carboxamide have a fungicidal activity, nothing is described in relation to their activity as useful fungicides

  in agriculture or horticulture Also a compound

  the compounds of the invention has been described as an example

  in Japanese Patent No. 52-24003 (1977), however

  this compound cited as an example is N-1- (1,2,4-triazole-4-

  yl) -2,2,2-trichloroethyl-formamide and the free valence of the triazole radical is not in position 1, as it is

case of the compounds of the invention.

  Following extensive studies concerning the synthesis

  and the selection of new N-1-triazole derivatives

  (1) -yl-2,2,2-trichloroethyll-carboxamide for the purpose of

  point a new fungicide for use in agriculture and horticulture.

  culture, it has been found that the compounds represented by the general formula (I) have an excellent fungicidal activity against oidium of cereals, vegetables, fruit trees and flowering plants and the invention

  based on the discoveries that result.

  As the compounds according to the invention

  excellent preventive and curative effects against

  as well as a powerful systemic action within the plant to which it is applied, it is possible to fight directly or systemically against plant disease.

  in other words, the systemic action of the compounds of the

  vention in plant tissues has many advantages.

  in the field of plant disease control For example, we can fight effectively

  against a phytopathogenic fungus that has invaded

  of plants and against a phytoplankeal fungus.

  pathogen infecting seeds by using such a fungicide

  In addition, in the case of applying a

  aerial parts of cultivated plants, even if the fungicide does not cover the vegetal surfaces of the plant, the systemic fungicide can be used to control the disease. Such a systemic fungicide can be applied by soil treatment or seed treatment, which allows a saving of powder during

application of the fungicide.

  On the other hand, the compound according to the invention is without

  danger for vertebrates, including man and fish

  sounds, and can be applied to agricultural crops without

practically harming them.

  The object of the invention is to provide novel derivatives of the type

  N-1-triazole- (1) -yl-2,2,2-trichloroethyllecarboxamide

  presented by the general formula (I) and an agent against

  oidium having excellent systemic activity.

  The invention relates to novel N-type derivatives

  1-triazole- (1) -yl-2,2,2-trichloroethyl-carboxamide

  titué represented by the general formula (I):

1

R-C-NH CH-N (I)

RC NH 1 ill-

C C 13

  wherein R represents a hydrogen atom or a radical

  methyl, ethyl, 2-trifluoromethylphenyl, 2-hydroxy-dialkylate

  phenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butyl-

  phenyl, 2-chloro-4-nitrophenyl, benzyl or a radical of the formula: R 1> (II) R wherein R 1 and R 2 which are the same or different respectively represent a hydrogen, fluorine, chlorine, bromine or iodine or a methyl radical or

  methoxy, and an agent against oidium containing as an ingredient

  A compound represented by the general formula (I) is active.

  Examples of N-11-triazole derivatives (1) -

  yl-2,2,2-trichloroethyl-carboxamide that can be used

  as active ingredients of an agent against oidium

Table 1.

TABLE I

  Some compounds according to the invention No. of the chemical name of the compound Pontdefuio compound 1 Nl 1- (1,2,4-triazo-L-1-yl) -2,2,2-trichloroethyllformamide 115-117 2 Nl 1- (1 2,4-Triazol-1-yl) -2,2,2-trichloroethyllacetamide 172-174 3 1 Nl 1- (1,2,4-Triazo-L-1-yl) -2,2,2-trichloroethyllpropionamide 157 N1 1- (1,2,4-Triazo-L-1-yl) -2,2,2-trichloroethylibeflzamide 105-108 N1 1- (1,2,4-Triazo-L-1-yl) 2,2,2-trichloroethyl II-2 140-142 chlorobenzamide 6 Nl 1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-3,171-172 chlorobenzamide 7 Nl 1- (1) 2,4-triazob-E-1-yl) -2,2,2-trichloroethyl-4 179-181 chlorobenzamide 8 Nl 1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll- 2,4 164-166 dichlorobenzamide 9 Nl 1- (1,2,4-triazol, -1-yl) -2,2,2-trichloro-ethyl-3,4-dichloro-1,4-dichlorobenzamide 1- (1,2, 4-triazo-1-yl) -2,2,2-trichloroethyl-2,6-19-19l Nl 1- (1,2,4-triazo-3-L-1-yl) -2,2,2-trichloroethyl IJ -3.5-1919 i

dichlorobenzamide

  ta Ni TABLE i (continued 1) Chemical Name of Compound Pontdefuio Compound (C 12 Nl 1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-2,149-151 bromobenzamide 13 Nl 1- (1,2,4-Triazo-1-yl) -2,2,2-trochloroethyl-16-4-methylbenzamide 1418 14 Nl 1- (1,2,4-triazo-2-yl) 2-2,2-trichloroethyl-4-methoxybenzamide N-1- [1,2,4-triazoled-1-yl) -2,2,2-trichloroethyll-2-methoxybenzamide 2,4-triazo-2-yl) -2,2,2-trichloroethyl-2-15-N-1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-1-yl; 2,6 170-172 dif 11 uorobenz-amide 18 Nl 1- (1,2,4triazo 2 e-1-yl) -2,2,2-trichloroethyl-2 153-156 trifluoromethylbenzamide 19 Nl 1- (1,2 4-Triazol-1-yl) -2,2,2-trichloroethyl-2,157-158 iodobenzamide Nl 1- <1,2,4-triazo-2-yl) -2,2,2-trichloroethyl- 2 171172 hydroxybenz amide Lnl TABLE 1 <suite 2) No of the chemical name of the compound Melting point 21 Nl 1- <1,2,4-triazo-13-d-yl) -2,2,2-trichloroethyl-2 154-156 acetoxybenzamide 22 Nl 1- <1,2,4-triazole L 1 yl) -2,2,2-trichloroethyl-4,141-152 isopropyl benzamide 23 Nl 1- <1,2,4triazol-1-yl) -2,2,2-trichloroethyl-4-tert 142-144 butylbenzamide 24 Nl 1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl D-2,6 178-179 dimethylbenzamide Nl 1- (1,2,4-triazollyl) -2,2,2 2-Trichloroethyl-2chloro 189-191 4-nitrobenzamide 26 Nl 1- (1,2,4-triazole-11-yl) -2,2,2-trichloroethyl 175-176 phenylacetamide 27 Nl 1- (1,2,4-triazolone) -1-yl) 2,2,2-trichloroethyl-2,5 166-168 dichlorobenzamide <% O

  A useful compound can be synthesized as an ingredient

  The active ingredient in the invention is as follows: ## STR1 ## in a C 13 organic solvent C 1 i 3

O

It t

R C NH_ CH -N

  CC 13 in which R has the same meaning as above More

  particularly, by stirring an N- (1,2,2,2-tetrachloroethyl) -

  carboxamide in an organic solvent such as acetonitrile

  at the ordinary temperature for a few hours after

  the addition of a quantity between the molar equivalence

  With a slight excess of 1,2,4-triazole and an equimolecular amount of triethylamine, the desired compound can be obtained. The invention is illustrated in more detail by the

following examples.

EXAMPLE 1

  Synthesis of N-1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll

formamide (compound No. 1).

  In a solution of 3.1 grams (0.015 mole) of N

  (1,2,2,2-tetrachloroethyl) formamide in 40 ml of acetonitrile

  1 ml (0.015 mole) of 1,2,4-triazole is added and, after addition of 1.5 grams (0.015 mole) of triethylamine,

  To the mixture, the mixture is stirred for 2 hours at room temperature.

  The water is carefully washed with water

  this white solid obtained by concentration of the

  reaction mixture under reduced pressure and after drying

  Ge, it is recrystallized from benzene to obtain the compound No.1, melting at 115-117 ° C. in the form of crystals.

  whites weighing 2.0 grams (55% of theoretical yield).

  The results of the infrared absorption and nuclear magnetic resonance analysis of the compound No 1 obtained are as follows: Infrared absorption strips (K Br tablet):

3140 (NH) and 1700 (CO) cm 1.

  NMR spectrum (d 6 in acetone), 6 (ppm): 7.30 (1H, d, J = 11Hz, CH) 8.10 and 8.99 (each 1H, s, proton of the ring triazole), and

  8.48 (1H, s, COH) and 9.30 (1H, m, NH).

EXAMPLE 2

  Synthesis of N-1- (1,2,4-triazol-2-yl) -2,2,2-trichloroethylll

acetamide (compound No. 2).

  In a solution of 3.3 grams (0.015 mole) of N

  (1,2,2,2-tetrachloroethyl) acetamide in 40 ml of acetonitrile

  trile, mix 1 gram (0.015 mole) of 1,2,4-triazole

  and after mixing 1.5 grams (0.015 mole) of triethyl

  amine, the whole is stirred for 4 hours at room temperature.

  The white solid obtained by concentration under reduced pressure of the reaction mixture is carefully washed with water, dried and then recrystallized from benzene to give 2.9 grams (76% of theoretical yield) of compound No. 2 melting at 172174 C as white crystals The results of

  infrared absorption and magnetic resonance analysis

  No. 2 thus obtained are infrared absorption bands (K Br tablet): -1 3130 (NH) and 1690 (CO) cm NMR spectrum (d 6 in acetone), 6 ( ppm): 2.13 (3H, s, CH 3), 7.30 (1H, d, J = 11Hz, CH), 8.14 and 9.02 (each 1H, s, proton of the cycle

triazole), and 9.03 (1H, m, NH).

EXAMPLE 3

  Synthesis of N-1- (1,2,4-triazoel-yl) -2,2,2-trichloroethyll

propionamide (compound No. 3).

  In the same way as in Example 1, from 3.6 grams of N- (1,2,2,2-tetrachloroethyl) -propionamide (0.015 mole) in 50 ml of acetonitrile, 1 gram (0.015

  mole) of 1,2,4-triazole and 1.5 grams (0.015 mole) of

  ethylamine, Compound No. 3 was synthesized by stirring the entire system for 3 hours at room temperature after recrystallization from ethanol in

  white matter obtained by concentrating the reaction mixture

  Under reduced pressure, careful washing with water and drying, Compound No. 3 is obtained in the form of purified white crystals, melting at 157 ° -158 ° C. and weighing 3.0 grams (75% of theoretical yield). infrared absorption and magnetic resonance analysis

  number 3 are listed below.

  Infrared Absorption Tapes (K Br tablet): 3140 (NH) and 1700 (CO) cm-1 NMR (d 6 in acetone), 6 (ppm): 1.15 (3H, t, J = 8 Hz, CH 2 CH 3), 2.53 (2H, q, J = 8 Hz, CH 2 CH 3), 7.41 (1H, d, J = 11Hz, = CH), 8.27; and 9.18 (each 1H, s, proton of the triazole ring), and

9.00 (1H, m, NH).

EXAMPLE 4

  Synthesis of N-1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll

2 chlorobenzamide (compound No. 5).

  After suspending 2 grams (0.006 moles) of N- (1,2,2,2-tetrachloroethyl) -2-chlorobenzamide in

  ml of benzene, mix successively with the suspension

  0.42 grams (0.006 moles) of 1,2,4-triazole and 0.64 grams (0.006 moles) of triethylamine were added and the whole

  of the system for one hour at room temperature.

  After filtering off the separated white crystals

  The filtrate is concentrated under reduced pressure to give a pale yellow oily substance. The oily substance is purified by chromatography on a

  column of Wako-gel c-200 eluting with a mixture of ben-

  zene and acetone in a ratio of 10/1 by volume to obtain 1.6 gram of white crystals of compound No. 5

  melting at 140-142 ° C with a yield of 76%.

  The results of the infrared spectroscopic analyzes

  red and nuclear magnetic resonance spectroscopy of the compound No. 5 thus obtained are as follows: Infrared absorption bands (K Br pellet):

3140 (NH) and 1678 (CO) cm 1.

  NMR (d 6 in acetone, 6 ppm): 7.3-7.58 (5H, m, C-H + benzene ring proton)

  8.02 and 9.00 (each 1 H, s, proton of the triazine cycle

zole) and

  9.50 (1H, broad, J = 10Hz, NH).

EXAMPLE 5

  Synthesis of N-1- (1,2,4-triazoelyl) -2,2,2-trichloroethyll

  2,4-dichlorobenzamide (Compound No. 8).

  After suspending 3.5 grams (0.01 mole) of N- (1,2,2,2-tetrachloroethyl) -2,4-dichlorobenzamide in

  ml of acetonitrile, mix successively with the suspension

  0.76 grams (0.011 moles) of 1,2,4-triazole and 1.1 gram

  me (0.011 mole) of triethylamine and shake together

  After 7 hours at room temperature, the filtrate is concentrated under reduced pressure to give a white solid. The solid is washed with water to obtain white crystals which are recrystallized from a small amount of acetonitrile in order to obtain 2%. 3 grams of Compound No. 8 melting at 164-166 ° C with a yield of .5%. The results of the analyzes of compound No. 8 thus obtained by infrared spectroscopy and nuclear magnetic resonance spectroscopy are shown below: Infrared absorption bands (K Br pellet):

3150 (NH) and 1690 (CO cm 1.

  NMR spectrum (d 6 in dimethylsulfoxide), δ (ppm): 7.40 (1H, d, J = 10Hz, c HG) 7.5% 7.8 (3H, m, benzene ring proton ), 8.20 and 9, 12 (each 1H, s, proton of the triazole ring), and

, 49 (1H, J = 10Hz, NH).

EXAMPLE 6

  Synthesis of N-1- (1,2,4-triazob-1-yl) -2,2,2-trichloroethyll-

  2,6-dichlorobenzamide (compound No. 10).

  After suspending 2 grams (0.0056 moles) of N- (1,2,2,2-tetrachloroethyl) -2,6-dichlorobenzamide in

  ml of benzene, mix successively with the suspension

  0.43 grams (0.006 moles) of 1,2,4-triazole and 0.64 grams (0.006 moles) of triethylamine were added and the whole was stirred for 8 hours at room temperature. After separating the white crystals by filtration, the benzene layer is washed twice with water, dried over

  anhydrous sodium sulphate and the benzene is discarded by

  tillation under reduced pressure to obtain 1.2 gram of

  white crystals that are recrystallized in a small quantity

  benzene to obtain 0.6 gram of compound No. 10

  melting at 195-196 C with a yield of 30%.

  The results of the infrared spectroscopic analyzes

  red and nuclear magnetic resonance spectroscopy of compound No. 10 thus obtained are shown below: Infrared absorption bands (K Br pellet): 3110 (NH) and 1685 (CO) cm NMR spectrum (d 6 in dimethylsulfoxide) , 6 (ppm): 7.38 (1H, d, J = 10Hz, CH), 7.48 (3H, s, benzene ring proton), 8.13 and 9.09 (each 1H, s, proton of the triazole ring), and

, 78 (1H, J = 10 Hz, NH).

EXAMPLES 7 to 11

  In the same way as in Example 6, we synthesize

  the compounds shown in Table 2 under the conditions set

  indicated in this table.

  The reaction of Example 7 is carried out at room temperature.

  while in Examples 8 to 11 we add

  1,2,4-triazole and triethylamine to the suspension

  cooled with ice water of each substituted benzamide in acetonitrile, and stirring is carried out until

  that the reaction mixture returns to the normal temperature

nary.

  The results of the analyzes by infrared spectroscopy

  frarouge and by nuclear magnetic resonance spectroscopy of the compounds thus obtained are included in

table 3.

TABLE 2

  Synthesis Conditions of Compounds Nos. 13, 17, 18, 21 and 24 of Examples 7 to 11 Quantity of Reagent No. 1 ** Reactant Time Sovn e Efficiency Exeplecomposed Reactant A * Reactant B * Recat C *** of Ritual Agitation time (hours) (g and%) (g and mole) 7 13 1.7 0.43 0.64 4 ac 9 tonitrile 1.0; 50

0.0056 0.006 0.006

  4.8 1.1 1.1 1.5 3 acetonitrile 2.9; 55

0.015 0.015 0.015

  9 18 2.5 0.53 0.78 4 acetonitrile 1.7; 63

0.007 0.0077 0.0077

  5.21 1.5 I acetonitrile 5.5; 95

0.015 0.015 0.015

  3.1 0.76 1.1 3.5 acetonitrile 1.4; 41.2

0.01 0.011 0.011

  t Notes Reactant A * Reactant B ** Reactant C **: N- (1 I, 2,2,2tetrachloroethyl) -2-methylbenzamide in Example 7, N- (1,2,2,2-tetrachloroethyl) -2 6-difluorobenzamnide in Example 8, N- (1 I, 2,2,2-tetrachloroethyl) -2-trifluoromethylbenzamide in Example 9, N- (1 I, 2,2,2-tetrachloroethyl) -2-acetoxybenzamide in Example 10 and NI 1,2,2,2tetrachloroethyl) -2,6-dimethylbenzamide in Example II I.

  : 1,2,4-triazole in all Examples 7 to 11.

  triethylamine in all Examples 7 to 11.

Ul i \> ta o

TABLE 3

  Example 7 8 9 10 111 Absorb strips 3140 (NH), 3110 (NH) 3130 (NH) 3410 (NH), 3140 (NH) infrared 1780 (OCO), (K Br tablet) 1670 (CO) 1680 (CO) 1660 (CO) 1665 (CO) 1675 (C 0) NMR spectrum 2.28 (3H, s, 7, 0-7.9 (3H, m, 7.4 (1H, d, J) 2.23 (3H, s, 2.15 (6H, s, (d 6 in -CH 3), 7.06-7.49 Hz cycle proton, CH), COCH 3) CH 3 x 2), dimethylsulfoxide), (5H, m = CH + benzene), 7.42 7.58-7.98 (4H, m, 7.287.91 (5H, 7.0-7.41 (3H, m.p. H, m, 6 (ppm) ring proton (1 H, d, J-10 Hz, m ring proton, proton proton of the benzene ring), 8.10 3 CH), 8.20 benzene), benzene ring benzene), and 9.05 and 9.11 (each 8.2 and 9.1 + 3 ° C-H), 7.48 (1H, d, (each 1H, s, 1H, s, proton of each 1H, s, 8, 32 and 9.29 J-10Hz, C-H), proton of the triazole ring cycle), proton of the ring (each 1H, s, 8.28 and 9.2 triazole), , 87 (1H, d, triazole), proton of the ring (each 1H, s, 21 (1H, d, J = 10Hz, NH) 10.7 (1H, d, J = triazole) proton of cycle J = 10 Hz, NH) 10 Hz, NH) , (1H, d, triazole) J = 10Hz, NH) 10.48 (1H, d, J = 10Hz, NH) mp 146148 170-172 153-156 154-156 178-179 (C, 1H, d, triazole) ) og r) Ln% oo

  Examples 12 and 13 below illustrate the preparation

  ration of two anti-oidium agents according to the

  invention, a wettable powder in Example 12 and a

  granular composition in Example 13.

EXAMPLE 12

  A wettable powder is prepared by spraying

  and mixing the following components and then sieving the mixture

  g parts by weight of compound No. 5 5 parts by weight of sodium lignosulfonate 3 parts by weight of sodium alkylsulfonate and

  42 parts by weight of diatomaceous earth.

EXAMPLE 13

  A granular composition is prepared by uniform mixing of the following components, mixing the mixture with the addition of a small amount of water, shaping the kneaded mixture into granules by extrusion and drying the extruded granules, and then sieving the dried granules: 8 parts by weight of the compound No. 40 40 parts by weight of bentonite parts by weight of clay and

  7 parts by weight of sodium lignosulfonate.

  Example 14 shows the effectiveness of oidium control agents according to the invention with respect to Erysiphe

  graminis (DC f, sp tritici, who is a pathogenic ascomycete

  not for wheat, in vivo when applying these agents on

  the aerial parts of wheat plants.

EXAMPLE 14

  On wheat shoots (variety: Norin 64)

  grown in 10 cm diameter pots (16 shoots / pot), at the three-leaf stage, each of the wettable powders having a composition similar to that of Example 12 is sprayed after dilution and dispersion in water at a temperature of

  concentration of active ingredient in water of 250 ppm.

  After natural drying of the leaves, the plants treated in the pots are sprayed with an aqueous suspension of: spores of Erysiphe graminis DC fsp tritici collected on the leaves of a wheat plant with oldium After leaving the pots in a greenhouse at about 250 C during

  days, the morbidity of shoots is studied by observing

  their morbid condition and evaluation according to the

next standard.

  The results of the study are shown in Table 4. Morbidity Significance of the disease state _ No lesion 0.5 Lesions occupy less than 10% of the total leaf area I Between 10 and 25% 2 Between 26 and 50 % 3 Between 51 and 75% 4 More than 75%

TABLE 4

  Results of oidium control by treatment of aerial parts of wheat shoots Active ingredient Morbidity Phytotoxicity Compound No. 1 0.5 None

2 O

3 O t.

4 0.5

O ,,

6 3

7 2

8 O

9 0.5

O *

11 1,

12 1

13 0.5

14 3

1

16 O

17 O O

18 O

19 O

O

21 O

22 0.5

23 0.5

24 0.5

O

26 O

27 O

  Control (no 4 comparative treatment 1) 1 Note:

  (1) Comparative anti-oidium control agent

  contains N-tridecyl-2,6-dimethyltetrahydro-1,4-oxazine as the active ingredient which is sprayed as an aqueous suspension at an active ingredient concentration

250 ppm.

  The following example shows the effectiveness of the oidium control agents according to the invention against Erysiphe graminis DC fsp tritici, in vivo by application to

wheat seeds.

EXAMPLE 15

  After soaking 30 seeds of wheat (variety:

  Norin 64) in an aqueous suspension of each of the

  Wettable agents having a composition similar to that of Example 12 with a concentration of active ingredient of 250 ppm, the seeds thus treated are sown in pots of 10 cm in diameter and the pots are kept in a greenhouse at about 25 ° C. 10 days to confirm sprouting and shoot development until

  two-leaved stage Then we spray on the

  in the two-leaf stage, an aqueous suspension of the spores of the same pathogenic ascomycete as in example 14 collected on wheat plants with oidium and the pots are left in the greenhouse at about 25 ° C. for 10 days. The morbidity is studied. wheat plants in the pots as in Example 14; the results appear in

Table 5.

TABLE 5

  Oidium control results by wheat seed treatment Active Ingredient Morbidity Phytotoxicity Compound No. 1 1 None

2 O

3 O

4 0.5 "

O "

6 1

7 2

8 1

O "

12 0.5

13 O

16 O

17 O O

18 O O

19 O O

O O

21 O O

22 0.5

23 0.5

24 O O

O

26 O O

27 1

Witness 4 Comparative 1) 1

  Note: Comparative 1): as in Table 4.

  The following example 16 illustrates the effectiveness of the anti-oidium agents according to the invention against Podosphaera leucotriche which is the pathogenic ascomycete responsible for apple oidium, in vivo on apple plants.

EXAMPLE 16

  An aqueous suspension of each of the

  wettable powders having a composition similar to that

  Example 12 on apple plants in pots in sufficient quantity to wet the leaf surfaces well and the pots are left for 2 weeks in a

  greenhouse in polyvinyl chloride at approximately 250 C to allow

  natural infection with Podosphaera leucotriche is a pathogenic ascomycete of the apple tree. The rate of morbidity of apple shoots depends on the appearance of ascomycete colonies on the leaves of apple trees according to the following classification. calculates the morbidity rate from formula (III)

  below; the results are shown in Table 6.

  Morbidity rate%: El (morbidity index) x (N) J (III) 4 x (N) i I I

  o Ni indicates the number of leaves with the mortality index

  bidity of i (eg 0-, 0.5; 1; 2; or 4) and N re-

  presents the total number of sheets examined.

  Morbidity index Morbid condition No fungal colonies on leaf surfaces 0.5 Colonies occupy less than 1% of leaf area 1 Colonies occupy less than 1% of leaf area 2 Colonies occupy less % of leaf area 4 Colonies occupy more than% of leaf area

TABLE 6

  Results of Oidium Control by Treatment of Apple Plants Active Ingredient Morbidity Rate e of Compound (%) Control (untreated) 34.4, 1 12.3 9.8 2.5 38.4 23, 2, 7 0.4 4.4 3.8 18.7 oooo 9, 7 o 24.3 19.1 ooo 3.5 71.6 None Il Il I l l l I l l l l l l l l l l l l If he I you l him there he

  Example 17 shows the effectiveness of the agents of

  against oidium vis-à-vis Erysiphe cichoracearum, which

  is a pathogenic ascomycete of tomato, in vivo, by

application to tomato plants.

EXAMPLE 17

  An aqueous suspension of each of the

  wettable powders having a composition similar to that

  Example 12 with a concentration of the active ingredient

  250 ppm on tomato shoots at the 5-leaf stage in three pots with one shoot / pot. After natural drying of the leaves, the plants are sprayed.

  of tomato an aqueous suspension of the spores of the ascomycec-

  pathogen collected on the leaves of

  tomato with oidium and 10 days after spraying.

  the morbidity of the plants by observation

  tomato plants treated in this way according to the standard

example 14.

  The results are shown in Table 7.

TABLE 7

  Results of the control of oldium by treatment of tomat plantsIngredient ingredient Morbidity Phytotoxicity Compound No. (%) 4 1 None

O

O

12 0.5

13 0.5

16 O

17 O

18 O

19 O and O and 21 o

22 0.5

23 O and

24 O "

O and

26 O "

  Control 4 (untreated) Example 18 below shows the effectiveness of the oidium control agents according to the invention with respect to Sphaerotheca fuliginea, which is a pathogenic ascomycete of cucumber plants when applied in vitro. vivo to cucumber plants.

EXAMPLE 18

  A suspension of each of the wettable powders having a composition similar to that of Example 12 is sprayed with a concentration of active ingredient of 250 ppm on cucumber shoots grown in

  pots 10 cm in diameter at the two-leaf stage

  tee: Sagami-hanjiro, one shoot / pot, three pots).

  After natural drying of the leaves of the shoots, cucumber plants are spread with a small brush, spores of pphaerotheca fuliginea collected on cucumber plants with oidium, and the leaves are left.

  pots in a greenhouse at around 250 C to allow the infection to

  After 7 days in the greenhouse, morbidity is assessed

  plants thus treated according to the standards below.

  Morbidity Morbid condition O No lesions observed 0.5 Lesions occupy less than 10% of leaf surface 1 Lesions occupy 10-19% of leaf surface 2 Lesions occupy 20-39% of leaf area 3 Lesions occupy 40 to 59% of the leaf surface 4 Lesions occupy 60 to 79% of the leaf surface Lesions occupy more than 80%

l of the leaf surface.

  The results are shown in Table 8.

TABLE 8

  Results of Control of Oidium by Treatment of Cucumber Plants Example 19 illustrates the effectiveness of the control agents against the iloidium according to the invention with respect to

  Sphaerotheca pannosa, which is a pathogenic ascomycete

  responsible for rose oidium, in vivo by application to

roses.

EXAMPLE 19

  It is applied to roses (variety: peace)

  in pots 30 cm in diameter, and naturally

  oidium, an aqueous suspension of each of the

  wettable powders having a composition similar to that

  Example 12 After natural drying of the rose bushes, the pots are left in a polyvinyl chloride greenhouse and 10 days after spraying, the morbidity is evaluated.

  provoked by the oidium of these plans from the observation

  Active Ingredient Morbidity Phytotoxicity Compound No. (%) Phytotoxicity 1 1 None

2 O ,,

3 O

4 0.5

O,

7 1

8 O

O -

12 0.5

0.5,

27 O

  Control 5 (untreated) Comparative 1) 0.5 N 1)

  Note Comparative as in Table 4.

  usual standards and then calculate the rate of

  morbidity as in Example 16; the results are

Table 9.

TABLE 9

  Results of the fight against oidium by treatment of rosebushes 1 28.4 None

2 10.6

3 9.5

4 6.6

O

6 23.7

7 19.8

8 12.5

O

12 3.6

13 1.2

13.5

16 O O

17 O

235Téo 18 O

19 1.9

4.3

21 O

22 17.7

23 21.8

24 11.1

O

26 O

27 10.6

  Control (untreated) 68.9 The invention is not limited to the examples described, it is capable of numerous variants accessible to those skilled in the art, depending on the applications envisaged and

  without departing from the scope of the invention.

  Active Ingredient Morbidity Rate Phytotoxicity Compound No. Tt i I

Claims (7)

  1 N-11-triazole- (1) -yl-2,2,2-derivatives   substituted trichloroethyl-carboxamide represented by the general formula (I): R C -NH H -N)   wherein R represents a hydrogen atom or a radical   methyl, ethyl, 2-trifluoromethylphenyl, 2-hydroxy-dialkylate   phenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-tert-butyl-   phenyl, 2-chloro-4-nitrophenyl, or benzyl or a radical of the formula: (I) R 2   in which R 1 and R 2 are the same or different and   each have a hydrogen, fluorine or chlorine atom,   bromine or iodine or a methyl or methoxy radical.   Derivatives according to claim 1, characterized   in that R represents the 2-chlorophenyl radical, 2,6-   dichlorophenyl, 2-fluorophenyl, 2,6-difluorophenyl, 2-   trifluoromethylphenyl, 2-acetoxyphenyl, 2-chloro-4- nitrophenyl or benzyl.   Compound according to claim 1, characterized   in that it is part of the group comprising N-1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-2-chlorobenzene amide.   Compound according to Claim 1, characterized in that it is part of the group consisting of N-1 (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-2,6-dichlorobenzamide. 29 2543997   Compound according to claim 1, characterized   in that it is part of the group comprising N-1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-2-fluoro   benzamide. Compound according to claim 1, characterized   in that it is part of the group comprising N-1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-2,6-difluoro-   benzamide. Compound according to claim 1, characterized   in that it is part of the group comprising N-El 1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-2-trifluoro-   methylbenzamide. Compound according to claim 1, characterized   in that it is part of the group comprising N-11-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-2-acetoxy-   benzamide. Compound according to claim 1, characterized   in that it is part of the group comprising N-1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-2-chloro-4- nitrobenzamide.   Compound according to claim 1, characterized   in that it is part of the group comprising N-1-   (1,2,4-triazol-1-yl) -2,2,2-trichloroethyl-phenylacetate   mide. Powdery composition for the control of oidium, characterized in that it contains an effective amount   at least one compound of the type N-1 1-triazole- (1) -yl-2,2,2-   trichloroethyllecarboxamide represented by the general formula (I) R-C -NH-CH-N () C C 13   in which R represents a hydrogen atom or a   methyl, ethyl, 2-trifluoroethylphenyl radical, 2- Pr, 1 X-997 I: J I, E   hydroxyphenyl, 2-acetoxyphenyl, 4-isopropylphenyl, 4-   tert-butylphenyl, 2-chloro-4-nitrophenyl or benzyl or a radical of formula R '   R 2 in which R 1 and R 2 are the same or different and respectively represent a hydrogen, fluorine, chlorine, bromine or iodine atom or a methyl or methoxy radical.   12 Composition according to claim 11, characterized   in that said compound is a member of the   taking N-1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-   2-chlorobenzamide, N-1- (1,2,4-triazol-1-yl) -2,2,2-   trichloroethyll-2,6-dichlorobenzamide, N-1- (1,2,4-   triazol-1-yl) -2,2,2-trichloroéthyll-2-fluorobenzamide,   N-1- (1,2,4-triazolyl) -2,2,2-trichloroethyll-2,6-diis   fluorobenzamide, N-1- (1,2,4-triazol-1-yl) -2,2,2-tri-   chloroethyl-2-trifluoromethylbenzamide, N-1- (1,2,4-methyl) -2-   triazol-l-yl) -2,2,2-trichloroéthyll-2-acétoxybenzamide,   N-1- (1,2,4-triazol-1-yl) -2,2,2-trichloroethyll-2-   chloro-4-nitrobenzamide and N-1- (1,2,4-triazol-1-yl) -   2,2,2-trichloroéthyll-phenylacetamide.   13 Process for producing N-type derivatives   1-triazole- (1) -yl-2,2,2-trichloroethyl-carboxamide   titué, characterized in that it consists in adding an N-   (1,2,2,2-tetrachloroethyl) carboxamide with 1,2,4-   triazole and triethylamine in an organic solvent   and stirring the resulting mixture at room temperature.