US3885951A - Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds - Google Patents

Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds Download PDF

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Publication number
US3885951A
US3885951A US230505A US23050572A US3885951A US 3885951 A US3885951 A US 3885951A US 230505 A US230505 A US 230505A US 23050572 A US23050572 A US 23050572A US 3885951 A US3885951 A US 3885951A
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US
United States
Prior art keywords
acid
ester
chloroethanesulphinic
compound
bromoethanesulphinic
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US230505A
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English (en)
Inventor
Wolfgang Hofer
Klaus Lurssen
Robert Rudolf Schmidt
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Bayer AG
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Bayer AG
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Publication date
Priority claimed from DE19712110773 external-priority patent/DE2110773C3/de
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Publication of US3885951A publication Critical patent/US3885951A/en
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Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/02—Sulfinic acids; Derivatives thereof
    • C07C313/04—Sulfinic acids; Esters thereof

Definitions

  • Hal is preferably chlorine or bromine while R is preferably chlorine, bromine, hydroxyl, straight-chain or branched alkoxy of from 1 to 16 carbon atoms, straight or branched haloalkoxy of from 1 to carbon atoms, alkenyloxy of from 3 to 18 carbon atoms, alkynyloxy of from 3 to 5 carbon atoms or cyclohexyloxy.
  • R is preferably chlorine, bromine, hydroxyl, straight-chain or branched alkoxy of from 1 to 16 carbon atoms, straight or branched haloalkoxy of from 1 to carbon atoms, alkenyloxy of from 3 to 18 carbon atoms, alkynyloxy of from 3 to 5 carbon atoms or cyclohexyloxy.
  • R is preferably chlorine, bromine, hydroxyl, straight-chain or branched alkoxy of from 1 to 16 carbon atoms, straight or branched haloalkoxy of from 1 to carbon atoms, alken
  • the 2-haloethanesulphinic acid compounds of the formula (I) show a considerably greater plant-growth-regulating activity than 2-chloroethanephosphonic acid, which is chemically the nearest active substance with the same type of activity.
  • Some of the substances to be used according to this invention additionally have microbicidal and fungicidal activity.
  • the compounds according to the invention hence represent a valuable enrichment of the art.
  • the present invention provides a plant-growthregulating composition containing as active ingredient a compound of the formula (1) in admixture with a carrier, e.g., a solid or liquefied gaseous diluent or carrier or a liquid diluent or carrier containing a surface-active agent.
  • a carrier e.g., a solid or liquefied gaseous diluent or carrier or a liquid diluent or carrier containing a surface-active agent.
  • 2-chloroethanesulphinic acid chloride 2-chloroethanesulphinic acid bromide, 2-chloroethanesulphinic acid, -2chloroethanesulphinic acid methyl ester, 2-chloroethanesulphinic acid ethyl ester, 2-chloroethanesulphinic acid npropyl ester, 2-chloroethanesulphinic acid isopropyl ester, 2-chloroethanesulphinic acid n-butyl ester, 2-chloroethanesulphinic acid sec.-butyl ester, 2-chloroethanesulphinic acid tert.- butyl ester, 2-chloroethanesulphinic acid isobutyl ester, 2-chloroethanesulphinic"acid n-pen'tyl ester, 2-chloroethanesulphinic acid chloride, 2-chloroethanes
  • 2-chloroethanesulphinic acid 2'-methylpropenyl ester 2-chloroethanesulphinic acid penten-l '-yl ester, 2-chloroethanesulphinic acid l',l '-dimethylallyl ester, 2-chloroethanesulphinic acid octadecen-9-yl ester, 2-chloroethanesulphinic acid propargyl ester, Z-chloroethanesulphinic acid l-methyl-propargyl ester, 2-chloroethanesulphinic acid 1',l '-dimethylpropargyl ester, 2-chloroethanesulphinic acid cyclohexyl ester and the corresponding 2-bromoethanesulphinic acid derivatives.
  • a number of the substances that can be used according to this invention are known, for example 2-chloroethanesulphinic acid chloride, 2-chloroethanesulphinic acid (see Doklady Akad. SSR 157 (1964), No. 1, pages 139-142); 2-chloroethanesulphinic acid methyl ester and 2-bromoethanesulphinic acid methyl ester (see Chem. Ber.
  • the compounds of the formula (I) are new but can be prepared, as can the known analogues, in a simple manner using processes that are known in principle.
  • the sulphinic acid halides are obtained if the corresponding bis-(2-haloethane)- disulphides are halogenated, for example with chlorine in a molar ratio of 1:3, in the presence of inert solvents, such as methylene chloride, at temperatures between -60 C and 10 C, and the products are then reacted with alcohols.
  • the reaction products are isolated by stripping off the solvent in vacuo and distilling the residue.
  • the corresponding sulphinic acid halides are reacted with hydrolyzing agents or with the corresponding alcohols at temperatures between l C and +40 C in the presence of inert solvents, such as methylene chloride.
  • E-chloroethanesulphinic acid chloride was prepared analogously.
  • the active compounds that can be used according to this invention interefere with the physiological phenomena of plant growth and can therefore be used as plant-growth regulators.
  • the different effects of the active compounds depend essentially on the point in time of the application, with reference to the development stage of the seed or the plant, as well as on the concentrations applied.
  • Plant-growth regulators are used for various purposes that are connected with the development stage of the plant.
  • the seed dormancy can be broken in order to cause the seeds to germinate at a certain time at which germination is desired, but at which the seed itself shows no readiness to germinate.
  • the seed germination itself can, depending dogenic annual cycle, can be influenced by the active compounds, so that the plants for instance shoot or The shoot or root growth can be promoted or inhibited by the active compounds in manner dependent on the applied concentration.
  • the branching to the side can be multiplied by a chemical breaking of the apical dominance. This is of interest, for example in the propagation of plants by cuttings. In a concentrationdependent manner, however, it is also possible to inhibit the growth of side-shoots, for example in order to prevent the formation of side-shoots in tobacco plants after decapitation and thus to promote the leaf growth.
  • the influence of the active compounds on the foliage of the plants can be so regulated that a defoliation is achieved, for example in order to facilitate the harvest or to reduce transpiration at a time at which the plants are to be transplanted.
  • Fruit initiation can be promoted so that more, or seedless, fruits are formed (parthenocarpy). Under certain conditions, the premature fall of fruit can also be prevented, or the fruit fall can be promoted to a certain extent in the sense of a chemical thinning out. The promotion of the fruit fall can, however, also be so exploited that the treatment is effected at the time of the harvest, whereby a facilitation of harvesting occurs. With growth regulators it is also possible to accelerate or retard fruit ripening, to improve the fruit coloration and to cause fruits to come to ripeness within a short period of one another.
  • Yield increases with the aid of growth regulators can be attained by promotion of fruit initiation, by formation of larger fruits and by promotion of the vegetative growth. Further, a stimulation of the synthesis or of the outflow of secondary vegetable substances (for example latex flow of rubber trees) is possible.
  • the active compounds to be used according to the present invention can be converted into the usual formulations, such as solutions, emulsions, suspensions, powders, pastes and granulates. These may be produced in known manner, for example by mixing the active compounds with extenders, that is, liquid or solid or liquefied gaseous diluents or carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents.
  • extenders that is, liquid or solid or liquefied gaseous diluents or carriers
  • surface-active agents that is, emulsifying agents and/or dispersing agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid diluents or carriers there are preferably used aromatic hydrocarbons, such as xylenes, toluene, benzene or alkyl naphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethyl formamide, dimethyl sulphoxide or acetonitrile, as well as water.
  • aromatic hydrocarbons such as xylenes, toluene, benzene or alkyl naphthalenes
  • liquefied gaseous diluents or carriers liquids which would be gaseous at normal temperatures and pressures, e.g. aerosol propellants, such as halogenated hydrocarbons, e.g. freon.
  • ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, or ground synthetic minerals, such as highly-dispersed silicic acid, alumina or silicates.
  • emulsifying agents include non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkyl sulphonates, alkyl sulphates and aryl sulphonates, and preferred examples of dispersing agents include lignin, sulphite waste liquors and methyl cellulose.
  • non-ionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkyl sulphonates, alkyl sulphates and aryl sulphonates
  • dispersing agents include lignin, sulphite waste liquors and methyl cellulose.
  • the formulations contain, in general, from 0.1 to 95, preferably from 0.5 to 90% by weight of active compound.
  • the active compounds may be applied as such or in the form of their formulations or of the application forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, spray powders, pastes, soluble powders, dusting Solvent:
  • agents and granulates may take place in any usual manner, for example by watering, squirting, spraying, scattering and dusting.
  • concentrations of active compound can be varied within a fairly wide range. In general, concentrations of from 0.0005 to 2%, preferably from 0.01 to 0.5%, by weight are used.
  • the present invention also provides a method of regulating the growth of plants which comprises applying to the plants or a plant habitat a compound of the formula (I), alone or in the form of a composition containing as active ingredient a compound of the formula (I) in admixture with a diluent or carrier.
  • Emulsifier Emulsifier:
  • Young bean plants about 10 cm in height were sprayed with the preparations of active compound until dripping wet. After 14 days the growth increase was measured and the growth inhibition was calculated as a percentage of the growth increase of the control plants. means complete inhibition of growth, and 0% means no inhibition of growth.
  • part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and water was added until the desired concentration was reached.
  • Hal in the formula is chlorine or bromine and R is chloring, bromine, hydroxyl, alkoxy or haloalkoxy of from 1 to 8 carbon atoms, or cyclohexyloxy.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US230505A 1971-03-06 1972-02-29 Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds Expired - Lifetime US3885951A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712110773 DE2110773C3 (de) 1971-03-06 Verwendung von 2-Halogenäthansulfinsäuren und deren Derivaten zur Regulierung des Pflanzenwachstums

Publications (1)

Publication Number Publication Date
US3885951A true US3885951A (en) 1975-05-27

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US230505A Expired - Lifetime US3885951A (en) 1971-03-06 1972-02-29 Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds

Country Status (24)

Country Link
US (1) US3885951A (enrdf_load_stackoverflow)
JP (1) JPS5618562B1 (enrdf_load_stackoverflow)
AT (1) AT314271B (enrdf_load_stackoverflow)
BE (1) BE780256A (enrdf_load_stackoverflow)
BR (1) BR7201239D0 (enrdf_load_stackoverflow)
CA (1) CA987127A (enrdf_load_stackoverflow)
CH (1) CH568003A5 (enrdf_load_stackoverflow)
CS (1) CS176188B2 (enrdf_load_stackoverflow)
DD (1) DD96626A5 (enrdf_load_stackoverflow)
EG (1) EG10407A (enrdf_load_stackoverflow)
ES (1) ES400452A1 (enrdf_load_stackoverflow)
FR (1) FR2128660B1 (enrdf_load_stackoverflow)
GB (1) GB1320667A (enrdf_load_stackoverflow)
HU (1) HU164190B (enrdf_load_stackoverflow)
IL (1) IL38891A (enrdf_load_stackoverflow)
IT (1) IT953442B (enrdf_load_stackoverflow)
KE (1) KE2617A (enrdf_load_stackoverflow)
MY (1) MY7500057A (enrdf_load_stackoverflow)
NL (1) NL169401C (enrdf_load_stackoverflow)
PL (1) PL83269B1 (enrdf_load_stackoverflow)
RO (1) RO70848A (enrdf_load_stackoverflow)
SU (1) SU512691A3 (enrdf_load_stackoverflow)
TR (1) TR16683A (enrdf_load_stackoverflow)
ZA (1) ZA721461B (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927062A (en) * 1972-05-15 1975-12-16 Shell Oil Co Plant growth regulators
US4149873A (en) * 1977-01-12 1979-04-17 Ciba-Geigy Corporation Composition for the regulation of plant metabolism
US4227918A (en) * 1976-12-17 1980-10-14 Bayer Aktiengesellschaft Novel halogenoethyl sulphones and their use as plant growth regulators
US4357159A (en) * 1977-01-12 1982-11-02 Ciba-Geigy Corporation Haloethylthienylsulphonates for the regulation of plant metabolism
US4359334A (en) * 1980-04-28 1982-11-16 Gaf Corporation Composition for plant growth regulation
US4427439A (en) 1980-04-28 1984-01-24 Gaf Corporation Composition for plant growth regulation
WO1987005781A2 (en) 1986-03-31 1987-10-08 Rhone-Poulenc Nederlands B.V. Synergistic plant growth regulator compositions
US5123951A (en) * 1986-03-31 1992-06-23 Rhone-Poulenc Nederland B.V. Synergistic plant growth regulator compositions
US6274632B1 (en) * 1997-03-12 2001-08-14 Zeneca Limited Derivatives of 4,4-difluorobut-3-enylsulfinic acid and their use as pesticides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2442833A1 (fr) * 1978-11-29 1980-06-27 Conservatoire Nal Arts Metiers Procede de preparation de sels d'acides sulfiniques organiques

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654667A (en) * 1950-11-29 1953-10-06 Phillips Petroleum Co Sulfoxides as plant defoliants
US2999105A (en) * 1957-05-20 1961-09-05 Phillips Petroleum Co Process for preparation of esters of thiosulfinic acids
US3463803A (en) * 1966-10-28 1969-08-26 Chemagro Corp Polyhaloethyl and polyhalovinyl sulfinate and thiosulfinate esters

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654667A (en) * 1950-11-29 1953-10-06 Phillips Petroleum Co Sulfoxides as plant defoliants
US2999105A (en) * 1957-05-20 1961-09-05 Phillips Petroleum Co Process for preparation of esters of thiosulfinic acids
US3463803A (en) * 1966-10-28 1969-08-26 Chemagro Corp Polyhaloethyl and polyhalovinyl sulfinate and thiosulfinate esters

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927062A (en) * 1972-05-15 1975-12-16 Shell Oil Co Plant growth regulators
US4227918A (en) * 1976-12-17 1980-10-14 Bayer Aktiengesellschaft Novel halogenoethyl sulphones and their use as plant growth regulators
US4149873A (en) * 1977-01-12 1979-04-17 Ciba-Geigy Corporation Composition for the regulation of plant metabolism
US4357159A (en) * 1977-01-12 1982-11-02 Ciba-Geigy Corporation Haloethylthienylsulphonates for the regulation of plant metabolism
US4359334A (en) * 1980-04-28 1982-11-16 Gaf Corporation Composition for plant growth regulation
US4427439A (en) 1980-04-28 1984-01-24 Gaf Corporation Composition for plant growth regulation
WO1987005781A2 (en) 1986-03-31 1987-10-08 Rhone-Poulenc Nederlands B.V. Synergistic plant growth regulator compositions
US5123951A (en) * 1986-03-31 1992-06-23 Rhone-Poulenc Nederland B.V. Synergistic plant growth regulator compositions
US6274632B1 (en) * 1997-03-12 2001-08-14 Zeneca Limited Derivatives of 4,4-difluorobut-3-enylsulfinic acid and their use as pesticides

Also Published As

Publication number Publication date
IT953442B (it) 1973-08-10
ZA721461B (en) 1972-11-29
DE2110773A1 (de) 1972-09-28
KE2617A (en) 1976-04-30
FR2128660B1 (enrdf_load_stackoverflow) 1975-10-24
IL38891A (en) 1974-12-31
FR2128660A1 (enrdf_load_stackoverflow) 1972-10-20
PL83269B1 (enrdf_load_stackoverflow) 1975-12-31
CH568003A5 (enrdf_load_stackoverflow) 1975-10-31
MY7500057A (en) 1975-12-31
IL38891A0 (en) 1972-05-30
AT314271B (de) 1974-03-25
CS176188B2 (enrdf_load_stackoverflow) 1977-06-30
GB1320667A (en) 1973-06-20
DE2110773B2 (de) 1976-12-02
BE780256A (fr) 1972-09-06
SU512691A3 (ru) 1976-04-30
EG10407A (en) 1976-05-31
NL169401C (nl) 1982-07-16
DD96626A5 (enrdf_load_stackoverflow) 1973-04-05
TR16683A (tr) 1973-03-01
NL7202864A (enrdf_load_stackoverflow) 1972-09-07
RO70848A (ro) 1980-08-15
HU164190B (enrdf_load_stackoverflow) 1974-01-28
CA987127A (en) 1976-04-13
NL169401B (nl) 1982-02-16
BR7201239D0 (pt) 1973-05-03
ES400452A1 (es) 1975-07-01
JPS5618562B1 (enrdf_load_stackoverflow) 1981-04-30

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