DD151036A1 - USE OF HETEROCYCLIC VINEGAR DEREDATIVES AS PLANT GROWTH REGULATORS - Google Patents

Abstract

The invention has for its object to bring new means for Reguleirung the growth and development of plants for application, which act as a slow-release agent. Surprisingly, it has been found that heterocyclic acetic acid derivatives of general formula I have a high retarding activity. They can be used in all phases of the autogenous development of plants in the form of aqueous solutions, dust, aerosols, etc. both for the treatment of intact plants and for the treatment of individual organs.

Description

Use of Jtieterocycliechen acetic acid derivatives as Pflan zenwachstumsregulatoren

Field of application of the invention

The invention relates to the use of heterocyclic acetic acid derivatives in plant production as an agent for regulating plant growth and development processes.

Characteristic of known technical solutions At present, chemical substances are widely used as growth and development regulators in plant production. Through targeted intervention in metabolic processes, these chemical or xenobiotic compounds are able to influence the processes of plant ontogeny in a direction desired by humans, such as by regulation of growth, flowering, fruiting and ripening, change of rest periods, a delay of aging. In general, growth regulators are compounds with hormone-like action by interfering with the metabolism of auxins, Gibberelli-йеп, cytokinins or ethylene or as agonists or antagonists of natural phytohormones act. Of particular interest are so-called growth retardants. Your physiological if / ill health is very different. The retardants suppress the seepage, heave cell division and cell growth in the subapical meristem of some plants. They accelerate the flowering process

and / or multiply the number of flowers and have a sex-damaging effect, e.g. For example, retardants are also able to accelerate or retard the ripening of fruits and to regulate the aging processes of whole plants and parts of plants (or "plant organs"). They also increase the persistence of the plants against extraneous temperatures, against dryness, high salinity of the soil, against herbicidal influence, phytopathogenic fungi u. a.

The diverse physiological properties of the retardants cause their widespread use in plant production, but their successful application in practice depends on a number of not to be underestimated factors, such as the plant species to be treated, the developmental stage in which the plant is treated, the temperature, air and soil moisture, the presence of nutrients, etc. The best known compound used in practice is N- (2-chloroethyl) -triaethyl-aaaonium chloride (chlorcholine chloride or CCC). However, it has been shown in the agrochemical practice that CCC has a not yet in all respects has satisfactory effectiveness, which also includes a too small range of coverage with respect to the diverse agricultural requirements.

The use of piperidinoacetic acid arai as the plant growth and development regulators has already been proposed (V / P A 01 U / 198 375). These compounds surpass in some Paraaetern the previously known retardants such. B. the CCC. However, a major deficiency of all compounds previously used in practice is their relatively low physiological activity, which requires the application of high concentrations. However, this may lead to the occurrence of phytotoxicities leading to crop losses and is also associated with the potential danger of environmental pollution. "

Object of the invention

The object of the invention is to provide novel means of regulating the growth and development of plants which act as retardants and have a high physiological activity,

Explanation of the invention of the invention

It has surprisingly been found that heterocyclic acetic acid derivatives, such as 2-piperidino- (pyrrolidino-, morpholino-, Hexanethyleniiaino) abkb'ianlinge as hydrochlorides (Methylj odide or Me thy! Sulfate) of the general formula I:

(R ⁺ -CH ₂ -CO-ITH-R ₁ ) R ₂ "

(D

and R ₂ = Cl, Br, J, CH, OSOo have a high retarding activity and inhibit the aging processes of leaves, ie the chlorophyll degradation of eg cut leaves is delayed. In this regard, the liability / · exceeds · g. Compound classes unexpectedly those already known Retardanten · A particularly high activity in connection with a low Phytotoxisität possess the compounds 16 (2-H-methylpyrrolidino-acet-p-aethylanilidjodid) and 21 (N-methyl-hexa-Eethyleninino-acet-p-iaethylaniliajodid ) of Table 1 (Appendix D.

It can be seen from Table 2 (Appendix 2) that the compounds used have a retardation of chlorophyll degradation in leaves. The compounds 6 (2-piperidino-acetaido-6-ethoxybenzothiazole hydrochloride), 8-blorpholinoacetanido-S show a very strong antiproliferative activity -aethoxybenzimidazole hydrochloride), 10 (2-N-methylpiperidinoacetato-6-methoxybenzothiazole ethylsulfate), and 16 (2-U-methylpyrrolidino-acetoaido-benzthiazole methylsulfate). In a concentration of 10 "" M, these compounds harbored chlorophyll degradation, among other things 2.5-4 times that of the control.

The derivatives of piperidino (pyrrolidino, morpholino, hexaaethyleninino) acetic acid can be used in all phases of the ontogenetic development of plants in Fora of aqueous solutions, dusts, aerosols, etc. both for the treatment of intact plants and for the treatment of individual organs * For the solutions, dusts, aerosols etc. ", regardless of the form of the application, various crop protection agents can be added. The invention will be explained in more detail in the following with two exemplary embodiments and two tables.

Exemplary embodiments Example 1

To determine the sustained-release activity of derivatives of piperidino- (norpholino-, pyrrolidino- and hexanethylenind.no -) - acetic acid, the method of B · E · A. Knight, Η · F. Taylor, RL Wain (Ann. Appl. Biol. 63, 211-213, 1969) was applied to the retardation of the high-growth pea variety Alaska. All compounds were tested in equimolekularen concentrations 10, 10 ~ ⁴ and 10 "3 M · The mean values of three experiments are shown in Tab. 1 · For the above data it is seen that all include compounds to be tested on a high Retardanzaktivität, wherein the Most compounds on the same test object were more active than CCC.

low phytotoxicity has 2-N-ethylpyrrolidino-azetaraidobenzthiazole methylsulfate, N-ethylpyrrolidino-aceto-p-ethylanilidoodide, and U-methylhexamethylene-1-ylino-acet-p-methylanilide iodide.

Example 2

Slices of mature radish leaves (Raphue sativa) were tested according to the method of M. Bruce, J., H. Kefford (Life Sci. 4, 416-425, 1965) in order to assay the activity of the compounds for delaying the aging of cut leaves , The Radieschenblattscheiben were placed in Petri dishes on filter paper, which had been previously saturated sit sit solutions of the compounds to be tested or ait V / asser (control). The prepared samples were placed in a thermostat for 4 days in darkness and then the amount of chlorophyll was fixed. The results of three such experiments are shown in Tab.

From the data presented, it can be seen that, as a rule, all the compounds to be tested have activity in delaying chlorophyll degradation in the cut leaves. The hydrochlorides of 2-piperidino-azetanido-6-aethoxybenzothiazole and 2-morpholinoazetanido-6-β-benzylbenzidazole, the 2-N-methylpiperidino-aza-tanido-6-hydroxybenzothiazole azlate and 2-H-methylpyrrolidino, show a very strong aging activity -azetanidobenzthiazolaethylsulfat, which in a concentration of 10% of the chlorophyll decomposition, inter alia 2.5-4 times compared to the control hesaen. The data presented show that the derivatives of piperidino (pyrolidino, hexaaethylene-amino) acetic acid are highly effective regulators of plant growth and development.

Table 1

Retardant activity of some derivatives of piperidino (pyrrolidino, norpholino-hexamethylenimine) acetic acid

2 R , Санн. - ι / - length Stem length Fresh root 100 to R ₁ of the 2nd mass County-fresh 102 ta ι Inter ge v / icht 62 le medium 33 Act· 1OQ 100 100 103 100 control 103 99 97 100 83 100 I - Κ 96 89 75 100 27 62 (ZV t 68 66 41 87 87 i> 6+ CVt 100 96 93 73 91 98 ι ^ 92 85 81 99 38 86 -I / - - 63 68 54 89 99 57 ⁺ 3 100 95 88 73 105 95 - ₍ /. 95 96 86 103 42 92 D 76 71 55 94 101 6ß + 4 108 97 94 75 82 100 - ii 104 100 93 102 31 99 Q- 86 78 71 95 94 71 + 5 H , R., / Rp Κοηζ · 98 96 91 80 80 97 Ro 10 "" ^η M 91 75 78 97 30 83 Q * 73 66 53 89 95 60+ 6 91 101 106 77 89 98 85 94 93 97 39 90 77 71 67 98 64+ 7 H 5 93 97 92 76 97 Jh J 4 88 97 101 105 93 69 64 57 92 61 + 8th 5 74 CH ₃ OSO ₃ 4 3 5 - CC 4 3 5 - - »ι- 4 3 5 ⁶ I; 3 5 - - // - 4 3 5 - ~ "-4 3

¹³ O ~~ "-" ~

97

90 60

94 82

100 81 75

97 107

86

92 77

92 45 37

92 103 89 102 73 65

5 89 98 102 100 99 98 10 -U- -H-CH ₃ OSO ₃ 4 82 86 88 84 79 84 3 84 54 62 74 31 61 ⁺ Ct * 5 98 98 96 95 109 99 ¹¹ Q 84 79 71 79 56 74 3 79 72 64 70 34 64 5 99 99 100 100 107 101 ¹² Q; - ι / - -i- 4 91 79 65 71 52 72 3 61 72 43 66 22 5β ⁺

α -

<* Э

97 95 101 102 117 103 100 81 74 72 61 78 46 56 25 72 16 43+

5 97 100 98 97 94 97 15 -I / - -U-CH ₃ OSO ₃ 4 85 81 76 78 68 78 3 96 77 75 66 40 71 5 97 97 94 104 123 107 16 (j ' 3 89 70 89 62 84 40 100 72 124 26 97 54 5 102 98 101 106 108 103 ti _ _{| и |} - ^ _. 94 83 80 89 82 86 3 76 52 48 70 46 58

91 99 90 104 105 98

91 97 93 102 120 101

phytotoxicity

if - U- J

97 91

68

99 87

103 96

125 91

52

⁴ - 'η

Cl

91 96 97 105 129 104

92 94 75 102 97 92

Phytotoxicity .

- "- J

95 108 103 110 90 88 78 82 64 61 50 69

136 110 43 76

39 57

⁺ Phytotoxic Syaptomas

Table 2

Influence of some derivatives of piperidino (pyrrolidino, iiorpholino) acetic acid on the retardation of chlorophyll degradation in radish leaf discs

/ EUCH ₂ COHH. R ₁ / R ₂ ro " J concentration Yes 4 10 ^"n M IT R R CH ₃ OCH ₃ 100 control (Water) Cl 5 100 3 I - Il 110 2 U -fl 102 156 128 3 Q - -ii If 120 99 254 4 Q - - "I Il 102 110 170 5 Q V ^ OCH J 96 85 188 6 Q. - -il CH ₃ OSO ₃ 91 88 240 7 Qs - -II-- 88 105 355 8th и 97 106 346 9 Q ₄ ~ • (( 106 139 10 81 404

40

11 О H VS) Cl 84 128 121 12 п Il - "- 89 84 214 13 Q, π - 85 88 63 H J 85 82 95 15 Il CH ₃ OSO ₃ 81 60 112 16 р. bg _hj vs) CH ₃ OSO ₃ 102 85 250

Claims (1)

Use of heterocyclic derivatives of esacetic acid as regulators of plant growth and development, characterized in that piperidino (pyrrolidino, morpholine, hexaethyleneethylene) acetic acid derivatives of general formula I: in which (R ⁺ -CH ₂ -CO-UH-R ₁ (D ^{ϊ + =} \ Jf \ / CH-3 Г \ Лн ₃ S-Jk 'CH, R ₁ = μ СИ. LVA оси. and R ₂ = Cl, Br, J, CH-jOSO, may be in Fora of aqueous solutions, dusts, aerosols, optionally in combination with crop protection agents.