Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
  • A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom

Definitions

• the present invention relates to the application as plant growth factors of O-phenyl hydroxylamine and certain of its derivatives.
• a subject of the invention is the application, as plant growth factors, of the compounds of formula (I):
• R 1 represents a hydrogen atom
• R 2 represents a hydrogen atom
• R 3 represents a hydrogen atom, a methyl radical in 2,3 or 4, a chlorine atom in 3 or 4, a bromine atom or a CF 3 radical in 4 or an NO 2 radical in position 2 or 4, or else R 2 represents a nitro radical in 2 and R 3 represents a nitro radical or a CF 3 in 4 radical
• R 1 represents a nitro radical at 2 and or R 2 represents a nitro radical at 4 and R 3 a nitro radical at 6, or R 2 represents a nitro radical at 6 and R 3 a CF 3 radical at 4, and of their addition salts with acids organic and mineral.
• the compounds of formula (I) are known compounds: see on this subject CA 82 (21) 139982 h, CA 83 (5) 43608, CA 88 (9) 65075 d, CA 93 (15) 149948 t, CA 68 ( 5) 21678 W, or the German patent 2,059,190.
• addition salts with acids mention may be made of those formed with strong acids such as hydrochloric, hydrobromic, sulfuric, nitric or else trifluoroacetic.
• the compounds of formula (I) and their salts with acids had not found any application in agriculture until now.
• the Applicant Company has now found that the compounds of formula (I) and their salts with acids can be used as plant growth factors.
• the products of formula (I) and their salts with acids can, in general, be used in agriculture to improve the physiological state of cultivated plants and obtain an increase in the weight of crops.
• the invention more particularly relates to the application as plant growth factors of O- (4-nitro phenyl) hydroxylamine, O-phenyl hydroxylamine and O (4-chlorophenyl) hydroxylamine , as well as their addition salts with organic and mineral acids and in particular their hydrochlorides.
• a subject of the invention is also in particular the application as plant growth factors of the following compounds: - O- (2-nitrophenyl) hydroxylamine;
• a more particular subject of the invention is therefore the application as growth factors of so-called "C 3" plants, products of formula I and their salts and in particular products of formula I mentioned above.
• the compounds of formula I have the effect of reducing the inhibition by oxygen of photosynthesis.
• the very nature of the mode of action by reducing the inhibitory effect of oxygen on photosynthesis opens up very remarkable and surprising prospects for the future for improving the yield of crops of so-called C 3 plants.
• This mode of action also has the consequence of substantially increasing the quantity of oxygen released into the atmosphere by the treated plants, which offers a non-negligible ecological aspect in the face of the current problems of increasing amount of CO 2 in the atmosphere.
• a subject of the invention is also the compositions used as plant growth factors, characterized in that they contain an effective amount of products of formula (I), and very particularly of the following compounds:
• compositions according to the invention can be in the form of granulated powders, suspensions, emulsions, solutions containing the active principle, for example, in admixture with a vehicle and / or an anionic, cationic or nonionic surfactant ensuring, among other things, a uniform dispersion of the substances of the composition.
• the vehicle used can be a liquid, such as water, alcohol, hydrocarbons or other organic solvents, a mineral, animal or vegetable oil, or a powder, such as talc, clays, si licates, kieselguhr.
• the solid compositions presented in the form of dusting powders, wettable powders or granules, can be prepared by mixing the active compound with an inert solid or by impregnation of the solid support with a solution of the active principle in a solvent which is then evaporates.
• compositions can contain, as active principle, one or more other substances having properties influencing the growth of plants.
• compositions of the invention are, of course, used in doses sufficient to exert their activity as plant growth factors.
• doses of active ingredient in the compositions vary in particular according to the plants to be treated, the nature of the soil, the atmospheric conditions and the state of advancement of the vegetation.
• compositions used as growth factors according to the invention generally contain from 10 to 80% by weight and preferably from 10 to 50% by weight of products of formula (I) or their salts.
• the amounts of active substance applied vary between 20 g / ha and 500 g / ha and preferably between 40 and 120 g / ha.
• Example 1 Emusible concentrate
• a composition was prepared containing by weight 15% of 4-nitrophenyl hydroxylamine, 6.4% of Atlox 4851 (oxyethylenated triglyceride combined with a sulfonate, acid number 1.5), 3.2% of Atlox 4855 ( oxyethylenated triglyceride combined with a sulfonate, acid number 3) and 75.4% xylene.
• Example 2 Wettable Powder
• a composition was prepared containing by weight 15% of O-phenyl hydroxylamine hydrochloride, 6.4% of Atlox 4851 3.2% of Atlox 4855 and 75.4% of xylene.
• Example 4 Wettable Powder A wettable powder was prepared containing 25% O- (4-chlorophenyl) hydroxylamine, 15% Ekapersol, 35% Zeosil 39 and 25% Vercoryl S.
• Example 5 Study of the activity of the products of formula I on the "Warburg” effect.
• the products of formula I have the property of reducing the inhibitory effect of oxygen on photosynthesis (Warburg effect), which results in stimulation of photosynthesis and an increase in the yield of the crop.
• the test is carried out on excised wheat leaves, placed in floatation either on distilled water, or on a solution of product to be studied (10 mmol per liter).
• the sheets are placed in sealed glass chambers under an illumination of 300 W / m2 and the temperature of which is regulated at 25 ° C; the atmosphere in the room is continuously renewed either with normal air (21% O 2 - 350 ppm CO 2 ), or with pure oxygen: almost 100%).
• 0.09 ⁇ mol of 14 CO 2 is introduced (specific activity: 22 mCi / mM) and the leaves are left for 15 minutes in the light in the presence of radioactive carbon dioxide.
• the leaves are then immersed in liquid nitrogen and stored. They are then burned to determine the amount of 14 CO 2 fixed by photosynthesis. The results are expressed in terms of radioactivity fixed between control sheets and treated with the products to be studied.
• Example 6 Study of the activity of 0- (4-nitrophenyl) hydroxylamine on the toxicity of oxygen vis-à-vis the photosynthesis of protoplasts of wheat leaves.
• the wheat leaf protoplasts are extracted according to conventional isolation techniques by maceration of plant material in cellulosolytic and pectinolytic enzyme solutions as well as by differential centrifugation and filtration.
• the inhibitory effect of oxygen is measured on the protoplast suspensions according to the treatment with O- (4-nitrophenyl) hydroxylamine.
• the test consists in varying the ratio of the concentrations of oxygen and of HCO 3 in the suspension of protoplasts in the presence and in the absence of O- (4-nitrophenyl) hydroxylamine.
• Photosynthesis is evaluated by measuring the oxygen given off by the protoplasts in light and carried out with the CLARK type electrode at a temperature of 25 ° C.
• the illumination in the measuring cell corresponds to 250 W / m2.
• the values of the photosynthesis rates observed as a function of the ratio (H CO 3 ) / (O 2 ) in the presence or in the absence of O- (4-nitrophenyl) hydroxylamine are collated in Table 1:
• O- (4-nitrophenyl) hydroxylamine greatly decreases the toxicity of O 2 to photosynthesis, as evidenced by increases in photosynthesis rates of treated wheat protoplasts, especially when the relative concentrations of bicarbonate and oxygen are such that photosynthesis is inhibited ("Warburg" effect).
• Example 7 Study of the activity of O- (4-nitrophenyl) hydroxylamine on the toxicity of oxygen with respect to the photo synthesis of intact chloroplasts, extracts of wheat leaves.
• the intact chloroplasts or of class A, according to the terminology of DO HALL (Nature 235: 125-126, 1978), are capable of fixing carbon dioxide and giving off oxygen at rates equivalent to those of a leaf. whole (50 to 250 umoles of O 2 released per mg of chlorophyll per hour).
• the chloroplasts used in this test are extracted from the protoplasts of wheat leaves and obtained by gentle mechanical rupture of the cell walls by osmotic shock, filtration and centrifugation on density gradients.
• Photosynthesis is evaluated by measuring the release of oxygen from the suspension of intact chloroplasts, in the light, in the presence of HCO 3 and O 2 , the relative proportions of which vary, and in the presence or absence of O (4-nitrophenyl) hydroxylamine 40 umolaire.
• O- (4-nitrophenyl) hydroxylamine stimulates the photosynthesis of chloroplasts, protoplasts and treated leaves compared to the control, by lifting the inhibition of oxygen on photosynthesis. This original property results in stimulation of the photosynthesis of the whole plant when it is treated either by root application, or by foliar application, with O- (4-nitrophenyl) hydroxylamine.
• the experimental device for measuring photosynthesis is based on a compensation method, starting from a set value of 350 ppm CO 2 .
• This device corresponds to a modification of the experimental setup proposed by M. ANDRE et al, Ann. Agron. 1979, 30 (2): 139-151.
• the plants are enclosed in glass chambers, with an internal volume of 6,250 liters, continuously swept at a speed of 0.5 m / sec -1 by 70% humidified air.
• the plants are lit by 5 OSRAM (HQI) lamps of 250 W each, for a 12 hour period.
• the CO 2 content of the air from the assimilation chambers is analyzed by an URAS 2-T infrared analyzer (Hartman and Braun).
• the CO 2 concentration is reduced to 350 ppm by injection of this gas from a compressed CO 2 bottle and the regulation ensured by Eurotherm regulators (type 070).
• the number of CO 2 injections is counted and recorded by SODECO meters and printers.
• the microclimatological parameters are recorded on SHESSEL recorders.
• this system is deactivated and only variations in CO 2 content are directly recorded after determination by the infrared analyzer.
• each plant (or group of plants) is only treated with O (4-nitrophenyl) hydroxylamine 7 days after the start of the measurements: this period serves as a "witness". After 7 days, the plants are treated either on the leaves or by the roots, with O (4-nitrophenyl) hydroxylamine and the photosynthesis and respiration measurements carried out continuously for 7 days; this
• 2 nd period corresponds to treatment.
• Foliar application The wettable powder previously described, containing 25% of O- (4-nitrophenyl) hydroxylamine is sprayed on the plants, so that the final concentration of active material is 10 -5 M. After drying of the suspension, the plants are replaced in the assimilation chambers and the photosynthesis and respiration measurements are undertaken. The results can be represented graphically by plotting the values of photosynthesis obtained during the hemoperiod and on the ordinate the respiration values measured during the nyetoperiod succeeding the hemoperiod.
• the values are expressed in time of opening of the solenoid valves making it possible to reach the set value of 350 ppm of CO 2 (photosynthesis) or the time of opening of these solenoid valves leading the air out of the rooms. towards CO 2 traps, in order to reduce the CO 2 content to 350 ppm (respiration).
• the graph showing the evolution u ratio between photosynthesis and respiration, after foliar application of O (4-nitrophenyl) hydroxylamine on wheat (Triticum Sativum - CAPITULE variety) is shown in Figure 1.
• the angle formed indicates the extent of the influence of the treatment, i.e. towards a favorable carbon balance (photosynthesis proportionally more stimulated than respiration: the right tilts towards the abscissa axis), or towards an unfavorable balance (respiration proportionally more stimulated than photosynthesis: the right inclines towards the ordinate axis).
• FIG. 1 shows that the carbon balance of wheat treated with O (4-nitrophenyl) hydroxylamine is favorable since photosynthesis is strongly stimulated by related to breathing. This stimulation comes from an increase in the rate of photosynthesis caused by O (4-nitro phenyl) hydroxylamine and comes from a lifting of the inhibition of photosynthesis by oxygen, as was shown in Examples 3, 4 and 5.
• the plants are grown on a nutrient solution of ARNON and HOAGLAND.
• O- (4-nitro phenyl) hydroxylamine is applied as a 25% wettable powder and diluted directly in the nutrient solution.
• the gas exchanges are measured using the same experimental device as that described at the start of Example 6.
• Results can be graphed using the modified Me.Cree and Silsbury method.
• O- (4-nitrophenyl) hydroxylamine was applied in the nutrient solution in the form of a wettable powder, at a final concentration of active ingredient of 10 -5 M.
• FIG. 2 Relative values of photosynthesis and respiration of wheat treated by root application with O (4-nitrophenyl) hydroxylamine.
• the inclination of the right towards the abscissa axis, obtained after treatment with O- (4-nitrophenyl) hydroxylamine clearly shows that photosynthesis is strongly stimulated compared to respiration.
• a stimulation in the case of wheat, of 28 to 55% is observed.
• Figure 3 Relative evolution of photosynthesis and respiration of beets after root application of O- (4-nitrophenyl) hydroxylamine.
• O- (4-nitrophenyl) hydroxylamine is used at doses of 40, 60 or 120 g / ha in 3 times or 1 time.
• Two tomato harvests are carried out. At each harvest, the yield in Kg is determined for 32 tomato plants, compared to an untreated control. The results are expressed as a percentage, the control being considered to have a percentage of 100%.
• the experimental results observed are summarized in the following table: B - Test on soybeans: The test is carried out on a soybean crop. We use a Fisher block with 6 repetitions. The elementary plots are 40 m2 (15 m X 2.66 m). An untreated control is included in each repeat. The test is carried out on a sandy calcareous clay soil.
• the treatments are carried out on the basis of 1000 l / ha, under a pressure of 3 bars with a backpack device of the Van der Weij type.
• O- (4-nitrophenyl) hydroxylamine is used at doses of 40, 60 or 120 g / ha once, twice or three times.
• the yield in kg is determined for 5 soybean plants. The results are expressed as a percentage, the control being considered to have a percentage of 100%.
• O (4-nitrophenyl) hydroxylamine has a growth activity with respect to soybeans.
• O (4-nitrophenyl) hydroxylamine has a growth activity with respect to soybeans.
• very significant increases in seed yield were obtained with O (4-nitrophenyl) hydroxylamine.
• the test is carried out on a soybean crop (variety IAC-6).
• the experimental device consists of a Fisher block with 4-repetitions.
• the elementary plots are 30 m2 and an untreated control is included in each repetition. There are 1, 2 or 4 applications.
• the processing stages are as follows:
• T 1 start of flowering (60 days after sowing)
• T 2 74 days after sowing
• O- (4-nitrophenyl) hydroxylamine is used in doses of 60, 120 and 240 g of active material per hectare, and applied in the form of a wettable powder at 25%.
• the yield expressed in kg of seeds per ha is compared to the control as a percentage thereof.
• O- (4-nitrophenyl) hydroxylamine increases the yield of soybean crops.
• O- (4-nitrophenyl) hydroxylamine was applied according to an identical experimental protocol.
• T 2 70 days after planting (pod development)
• T 3 80 days after planting (seed development)
• T 4 90 days after planting (early senescence).
• O- (4-nitrophenyl) hydroxylamine increases the yields of soybeans. Study of the effect of O (4-nitrophenyl) hydroxylamine on wheat crops.
• T 5 Milky grain
• T 6 Mealy grain
• the harvested seeds are weighed and the yields expressed in quintals / hectare.

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• 1982
  • 1982-01-28 FR FR8201321A patent/FR2520194A1/fr active Granted
• 1983
  • 1983-01-10 ZA ZA83142A patent/ZA83142B/xx unknown
  • 1983-01-17 DE DE8383400108T patent/DE3360080D1/de not_active Expired
  • 1983-01-17 AT AT83400108T patent/ATE12335T1/de not_active IP Right Cessation
  • 1983-01-17 EP EP83400108A patent/EP0085596B1/fr not_active Expired
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