Synthetic Plant Growth Regulators Research Articles

Relationship between Mefluidide Treatment and Abscisic Acid Metabolism in Chilled Corn Leaves

Mefluidide, N-(2,4-dimethyl-5[([trifluoromethyl]sulfonyl) amino] phenyl)acetamide, a synthetic plant growth regulator, was capable of triggering an increase in endogenous free abscisic acid content when corn (Zea mays L.) plants were grown in a nonstress, day/night, temperature regime (26 degrees C) with sufficient moisture supply. The relevance of such an abscisic acid increase prior to chilling exposure and the water relations during chilling are discussed in reference to the mefluidide protection of the chilled corn plants.

BIOCHEMICAL ASPECTS OF SYNTHETIC AND NATURALLY OCCURRING PLANT GROWTH REGULATORS, MONOGRAPH NO. 11 (Book).

Plant, Cell & EnvironmentVolume 8, Issue 4 p. 297-298 BIOCHEMICAL ASPECTS OF SYNTHETIC AND NATURALLY OCCURRING PLANT GROWTH REGULATORS, MONOGRAPH NO. 11 (Book). G. L. Steffens, G. L. SteffensSearch for more papers by this author G. L. Steffens, G. L. SteffensSearch for more papers by this author First published: June 1985 https://doi.org/10.1111/1365-3040.ep11604684Citations: 1AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume8, Issue4June 1985Pages 297-298 RelatedInformation

Synthetic plant growth regulators. VI. The partial synthesis of optically active (4β,15α)-18-Norkaurene-15-carboxylic acids from (4β)-18-norkauren-3-one by means of a pyrrolidinium ylide rearrangement

(4β)-18-Norkaur-16-en-3-one (4a) was alternatively acetalized (ethanediol/Dowex resin) or deoxygenated (tosylhydrazine/sodium borohydride); allylic bromination (N-bromosuccinimide) of the products, followed by alkylation of pyrrolidine gave primary allylic amines which were quaternized with chloroacetonitrile. Potassium t-butoxide-induced [2,3]-sigmatropic rearrangement, followed by acidic hydrolysis and Jones oxidation, gave respectively (4β,15α)-3-oxo-18-norkaur-16-ene-15- carboxylic acid (10a) and (4β,15α)-18-norkaur-16-ene-15-carboxylic acid. Reductions of (4a) and (10a) gave, with K-Selectride, axial (3β)- alcohols and, with sodium borohydride, mainly equatorial (3α)-alcohols. Details of a related conversion of (+)-phyllocladene into (15α)- phyllocladene-15-carboxylic acid are also recorded.

Synthetic plant growth regulators. V. The synthesis and crystal structure of a hybrid gibberellin-helminthosporic acid

(3aRS,4RS,6RS,8aSR)-5-Methyleneoctahydro-4H-3a,6-methanoazulene-4-carboxylic acid (7) has been synthesized and a detailed comparison made between its molecular structure and that of gibberellic acid (4). Indane-5-carboxylic acid (8) was converted by an alternating sequence of reduction and isomerization into the hydrindene acid (11). The diazomethyl ketone derived from (11) was transformed to cyclopropyl ketone (12) which was reduced by Li/NH3 with stereochemical inversion at the β-carbon to give a 1:3 mixture of ketones (13) and (14) respectively. Ketone (14) was then converted into the title acid (7) by a standard procedure. ��� Molecules of (7) crystallize in space group P2/c with a 7.782(1), b 11.055(1), c 14.559(3) Ǻ, β 116.05(1)°. The structure was solved by direct methods and refined by full-matrix least squares to a final R value of 0.053.

The effects of Z(3-phenyl-1,2,4,4-thiadiazol-5-yl)thio] acetic acid, a synthetic growth regulator, on auxin uptake by tobacco stem segments and crown gall suspension culture cells

Z(3-phenyl-1,2,4-thiadiazol-5-yl)thio] Acetic acid (PTAA) is a novel synthetic plant growth regulator causing disturbance of trophic responses and increased branching in one-year-old apple trees and a variety of other species. Its effects are similar to those of 2,3,5-triiodobenzoic acid (TIBA), an inhibitor of popular auxin transport. Auxin uptake by both tobacco stem segments and Parthenocissus tricuspidata crown gall tissue culture cells is stimulated 2–3 fold by both PTAA and TIBA, probably as a result of inhibition of a component of auxin efflux from the cells. The optimum concentration of PTAA is 0.5–10 μ mol/l at pH 4.5 and 10–100 μ mol/l at pH 6.5 for the crown gall cells and about 10 μ mol/l at Ph 6.0 for tobacco stem tissue. It is suggested that PTAA may be an inhibitor of polar auxin transport. Such inhibition may partly account for its growth-modifying properties.

Synthetic Plant Growth Regulators. The Synthesis of C-o-Carboxyphenyl Derivatives of Pyrimidine

Synthetic routes to o-carboxyphenyl derivatives of pyrimidine, required for testing as potential plant growth regulators, are described. 2-(4-Phenylpyrimidin-2-yl)benzoic acid (3), 2-(2-phenylpyrimidin- 4-yl)benzoic acid (4) and 2-(2-phenylpyrimidin-5-yl)benzoic acid (5) were prepared by utilizing amide-acid chloride intermediates in the generation of the pyrimidine ring in each instance.

Synthetic Plant Growth Regulators. IV. The Preparation of Hydroxylated Helminthosporic Acid Analogues

Sequential reduction (sodium borohydride, metal-ammonia, hydrogenation) of ketone (8) gave the hydroxy ketone (9) which was converted into olefin (10) (Wittig olefination) and thence to acid (14) by means of the [2,3] sigmatropic rearrangement of ylide (12) to (13). Acid (15) was similarly prepared from alcohol (11) which was obtained by deoxygenation of ketone (9). The tetrahydrocuminic acid (16) was hydroxylated (lithium diisopropylamine, oxygen); the new hydroxyl group was protected with a dichloroacetyl function and then converted into the diazoketone. Lewis-acid-induced cyclization of (17) gave the bicyclooctanone (18a) plus its Δ3-isomer (18b), both of which were reduced and hydrolysed to hydroxy ketone (19). Wittig methylenation of (19) gave olefin (20) which was rearranged by acid to ketone (21). Both (20) and (21) were elaborated further to the acids (6) and (25), respectively, by the procedures used in the preparation of acids (14) and (15).

Synthetic Plant Growth Regulators. III. The Preparation of Further Tricyclic Helminthosporic Acid Analogues with Gibberellin-like Properties

7-Methyl-7,8-dihydro-4a,7-methano-4aH-benzocycloheptene-2,6(9H,5H-dione (6) was prepared and reduced to a 3 : 7 mixture of the trans- and cis-decalin derived ketones (8) and (15). Each compound was further elaborated to the plant-growth-promoting acids (13), (14), (16) and (17). Dienone (5) was also reduced (NaBH4, hydrogenation) to a 7 : 3 mixture of the cis- and trans-decalin derivatives (11) and (9). The stereochemistry of (11), and by inference (12), was determined by correlation with the known ketone (7).

ChemInform Abstract: SYNTHETIC PLANT GROWTH REGULATORS. THE SYNTHESIS OF C‐O‐CARBOXYPHENYL DERIVATIVES OF SOME FIVE‐MEMBERED HETEROCYCLES

Chemischer InformationsdienstVolume 9, Issue 1 Heterocyclic Compounds ChemInform Abstract: SYNTHETIC PLANT GROWTH REGULATORS. THE SYNTHESIS OF C-O-CARBOXYPHENYL DERIVATIVES OF SOME FIVE-MEMBERED HETEROCYCLES R. L. N. HARRIS, R. L. N. HARRISSearch for more papers by this authorJ. L. HUPPATZ, J. L. HUPPATZSearch for more papers by this author R. L. N. HARRIS, R. L. N. HARRISSearch for more papers by this authorJ. L. HUPPATZ, J. L. HUPPATZSearch for more papers by this author First published: January 3, 1978 https://doi.org/10.1002/chin.197801238AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume9, Issue1January 3, 1978 RelatedInformation

Synthetic plant growth regulators. The synthesis of C-o-Carboxyphenyl derivatives of some five-membered heterocycles

Synthetic routes to o-carboxyphenyl derivatives of certain heterocyclic compounds, required for testing as plant growth regulators, were investigated. The preparation of 2-(5-phenyl-1,3,4-oxadiazol-2- yl)benzoic acid (3), 2-(5-phenyl-1,3,4-thiadiazol-2-yl)benzoic acid (4), 2-(5-phenyl-1H-1,2,4-triazol-3-yl)benzoic acid (5), 2-(3-phenyl- 1,2,4-oxadiazol-5-yl)benzoic acid (6), 2-(2-phenylthiazol-4-yl)benzoic acid (7), 2-(3-phenylisoxazol-5-yl)benzoic acid (8), 2-(5- phenylisoxazol-3-yl)benzoic acid (9) and chloro derivatives of (3), (4), (8) and (9) is described.

Two synthetic plant growth regulators affecting the development and reproduction of the cotton leaf worm Spodoptera littoralis (Boisd.) (Lepid. Noctuidae)

AbstractNewly moulted sixth instar larvae of S. littoralis were offered small discs of castor oil plant leaves treated with different concentrations of two plant growth regulators (Weedazol: 3‐amino‐1,2,4 triazol 25%) and (Alanap‐3: N‐1‐naphthyl phthalamic acid). These chemicals have retardant effect upon the sixth stadium especially in case of Weedazol and 20% of these larvae increased greatly in body weight and finally failed to pupate. The larvae of both treatments that succeeded to pupate decreased significantly in weight. Also the produced moths gave significantly decreased number of eggs in comparison to the control. The viability of eggs was also greatly affected.ZusammenfassungZur Wirkung zweier synthetischer Wuchsstoffe auf die Entwicklung und Vermehrung der Baumwolleule, Spodoptera littoralis (Boisd.) (Lepid., Noctudiae)Frisch gehäutete L6‐Raupen von S. littoralis wurden mit Rizinusblättern gefüttert, welche mit verschiedenen Konzentrationen zweier synthetischer Wuchsstoffe Weedazol (3‐amino‐1,2,4 triazol 25 %) und Alanap‐3 (N‐1‐naphthyl phthalamic acid) behandelt waren. Diese Chemikalien, insbesondere Weedazol, wirkten verzögernd auf die Entwicklung der L6‐Raupen. 20 % von ihnen erreichten übernormale Größe und waren nicht imstande, sich zu verpuppen. Umgekehrt zeigten die zur Verpuppung gelangenden Raupen ein normal niedriges Körpergewicht. Die hieraus hervorgehenden Falter erzeugten eine geringere Eizahl als jene der Kontrollzuchten. Auch war die Sterbequote der von ihnen abgelegten Eier sehr hoch.

EFFECTS OF THE PLANT GROWTH REGULATOR INDOLEBUTYRIC ACID ON THE GROWTH, DEVELOPMENT, AND REPRODUCTION OF THE WESTERN TENT CATERPILLAR, MALACOSOMA CALIFORNICUM PLUVIALE (LEPIDOPTERA: LASIOCAMPIDAE)

AbstractThe synthetic plant growth regulator indolebutyric acid delayed pupation, produced lighter pupae, and interfered with the larva-to-pupa molt of the western tent caterpillar, Malacosoma californicum pluviale (Dyar), when it was mixed with water (0.1 g/1.) in which cut foliage for rearing the larvae was kept. Treatment of very young larvae led to adults that produced more and better eggs than the controls. Treating older larvae produced antigonadotrophic effects.

Chlorobenzoyl Chloride and Methyl Chlorobenzoate as Synthetic Plant Growth Regulators

CBC (2,5-dichlorobenzoyl chloride) and MCB (methyl-2,5-dichlorobenzoate) function as plant growth regulators in a gaseous phase or in an aqueous solution. Sorghum [Sorghum bicolor (L.) Moench. ‘Martin’] and soybean [Glycine bicolor (L.) Merr. ‘Lee’] seeds were temporarily inhibited or delayed from germinating, but overcame the inhibition in time so there was no significant reduction in total germination. Seedlings produced from sorghum and soybean seed germinated and grown in aqueous solution of 35 μg/ml CBC or MCB were shorter and weighed less than control seedlings. Soybean seed treated with the vapors of CBC and MCB produced seedlings significantly reduced in dry weight as compared with that of controls. Foliar application of 500 or 1000 μg/ml of CBC significantly reduced the growth of soybean but not sorghum seedlings. Soybean seedlings treated with the vapors or an aqueous solution produced leaflets more narrow and thicker than control seedlings. A lethal response attributable to CBC or MCB was not recorded.

Synthetic plant growth regulators. II. The preparation of tricyclic helminthosporic acid analogues with gibberellin-like properties

Cyclopropyl ketone (13), prepared by the copper-catalysed decomposition of diazoketone (12), underwent specific cyclopropyl bond fission on reduction with lithium in liquid ammonia. Oxidation of the reaction product mixture followed by catalytic hydrogenation gave ketone (7) whose stereo-chemistry was established by degradation to trans-decalyl- 9-acetic acid (18), an authentic sample of which was prepared from trans-decalin-9-carboxylic acid. Ketone (7) was converted via its methylene derivative (21) to the pyrrolidinium salt (24) which underwent base induced [2,3]sigmatropic rearrangement, followed by hydrolysis, to give aldehyde (26). Acid (5) was formed by simple oxidation and converted by base catalysed isomerization of its methyl ester, then hydrolysis, into acid (6).

Synthetic plant growth regulators. I. The synthesis of (±)-14-Norhelminthosporic acid and related compounds

Cuminic acid (9) was converted by reductive methylation into 1,2,3,6-tetrahydro-4-isopropyl-1- methylbenzoic acid (12). Acid-catalysed cyclization of the diazomethyl ketone (8) derived from (12), followed by hydrogenation, gave the bicyclo[3,2,l]octanone derivative (7), which was then converted through the allylic bromide mixture of (18) and (19) into the p-toluenesulphonyldithiocarbazone (21) and the allylic ammonium bromide (25). The [2,3]-sigmatropic rearrangement of the dithio- carbene derived from (21) and the ylid derived from (25) afforded the dithioester (22) and pyrrolidine (26), respectively, from which the alcohol (24), aldehydes (27) and (28), and acids (5) and (6) were prepared. Bioassay of (5), (6), (27) and (28) indicated gibberellin-like properties for all these compounds with potency comparable with that of helminthosporic acid (2).

Auxin Transport: A New Synthetic Inhibitor

The new synthetic plant growth regulator DPX1840 (3,3a-dihydro-2-(p-methoxyphenyl)-8H-pyrazolo [5,1-a] isoindol-8-one) was examined for its effects on auxin transport. At a concentration of 0.5 mm in the receiver agar cylinders DPX1840 significantly inhibited the basipetal transport of naphthaleneacetic acid-1-(14)C in stem sections of Vigna sinensis Endl., Pisum sativum L., Phaseolus vulgaris L., Glycine max L., Helianthus annuus L., Gossypium hirsutum L., and Zea mays L. without significantly reducing total auxin uptake or recovery. The time sequence of the effect varied with the plant species. A similar inhibition of the basipetal movement of indoleacetic acid-1-(14)C was observed in intact seedlings of Phaseolus vulgaris L. In contrast to basipetal auxin transport DPX1840 had no significant effect on the acropetal movement of indoleacetic acid-1-(14)C in stem sections of Gossypium hirsutum L. Qualitatively the effect of DPX1840 on basipetal auxin transport was similar to that of other known auxin transport inhibitors. Quantitative differences, however, suggested the following order of activity: Naptalam>morphactin[unk]DPX1840>2,3,5-triiodobenzoic acid.DPX1840 also inhibited the lateral displacement of auxin. In horizontally placed stem sections of Helianthus annuus L. pretreated with DPX1840, the ratio of radioactivity from indoleacetic acid-1-(14)C in the upper versus the lower halves of the sections following basipetal indoleacetic acid-1-(14)C transport was approximately 50:50, whereas in the corresponding controls it was approximately 40:60.The data indicate that many of the characteristic effects of DPX1840 on plants, especially those which are known to involve auxin (e.g., epinasty, abscission, apical dominance, tropism), are due, at least in part, to its effects on auxin transport.

The effect of post harvest application of growth regulators on the yield of steroidal sapogenin from plant material

Incubation of harvested tuber of Dioscorea deltoidea Wall. and whole seed of Trigonella foenumgraecum L. with either synthetic or natural plant growth regulators increased the sapogenin yield by up to 35 per cent. The process is concentration and time dependent and is possibly linked to a role of the saponins.

Effects of Magnetic Fields on Tomato Ripening

ACCORDING to Duclaux1, Pasteur explored the possibility of the effect of a magnetic field on the production of optical isomers of tartaric acid. He theorized that the Earth's magnetic field caused tartaric acid to be of one optical isomer in nature, whereas laboratory synthesis produced a mixture of both isomers. Recently, Krylov and Tarakonova2 proposed an auxin-like effect of a magnetic field on germinating seeds. They called this effect magnetotropism. Auxins or, synthetic plant growth regulators have been used to stimulate ripening of immature fruits3.

OVULE ABORTION IN TRADESCANTIA AS AFFECTED BY AQUEOUS SOLUTIONS OF 2,4–DICHLOROPHENOXYACETIC ACID

OVULE ABORTION IN TRADESCANTIA AS AFFECTED BY AQUEOUS SOLUTIONS OF 2,4–DICHLOROPHENOXYACETIC ACID