WO2020127319A1 - Compositions de régulation de la croissance des plantes - Google Patents

Compositions de régulation de la croissance des plantes Download PDF

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Publication number
WO2020127319A1
WO2020127319A1 PCT/EP2019/085721 EP2019085721W WO2020127319A1 WO 2020127319 A1 WO2020127319 A1 WO 2020127319A1 EP 2019085721 W EP2019085721 W EP 2019085721W WO 2020127319 A1 WO2020127319 A1 WO 2020127319A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
oxo
ethyl
benzenesulfonamide
benzoxazin
Prior art date
Application number
PCT/EP2019/085721
Other languages
English (en)
Inventor
Mathilde Denise Lachia
Original Assignee
Syngenta Crop Protection Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection Ag filed Critical Syngenta Crop Protection Ag
Publication of WO2020127319A1 publication Critical patent/WO2020127319A1/fr

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to compositions comprising sulfonamide derivatives which are capable of acting as plant growth regulators, to processes for preparing the compositions, and to methods of using the compositions for controlling the growth of plants, improving plant tolerance to abiotic stress (including environmental and chemical stresses), inhibiting seed germination and/or controlling insect and fungi.
  • R 4 and R 5 together with the atom to which they are attached, are joined to form a C3-C 4 cycloalkyl or C4 heterocyclyl;
  • R 6 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C3-C 4 alkenyl, C3-C 4 alkynyl, and C 1 -C3 alkoxy-Ci-C4-alkyl;
  • Each alkyl moiety either alone or as part of a larger group is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, /so-propyl, n-butyl, sec-butyl, /so-butyl, tert- butyl or neo-pentyl.
  • the alkyl groups include Ci - C6 alkyl, C 1 -C 4 alkyl, and C 1 -C3 alkyl.
  • Alkoxyalkyl groups are an alkoxy group bonded to an alkyl (R-O-R), for example
  • R 1 , R 2a , R 2b , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Z, Y, R , Rx, Ry and R z are, in any combination, as set out below.
  • R 1 is selected from the group consisting of C 1 -C6 alkyl, C 1 -C6 haloalkyl, C3-C5 cycloalkyl-Ci-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, phenyl and a 4-6 membered heterocyclyl, each optionally substituted with one to three R x .
  • R 1 is allyl, cyclopropyl-methyl, 2,2,2-trifluoro-ethyl, 2,2-difluoro-ethyl or 3- fluoro-propyl. In one embodiment R 1 is 3-fluoro-propyl or n-propyl.
  • R y is selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylsulfanyl and C3-C 4 cycloalkyl.
  • R y is selected from the group consisting of halogen, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl.
  • R y is selected from the group consisting of cyano, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
  • Z is phenyl optionally substituted with one to three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl and C1-C4 haloalkoxy.
  • composition may further comprise an agriculturally acceptable formulation adjuvant.
  • yield includes, but is not limited to, (i) an increase in biomass production, grain yield, starch content, oil content and/or protein content, which may result from (a) an increase in the amount produced by the plant per se or (b) an improved ability to harvest plant matter, (ii) an improvement in the composition of the harvested material (e.g.
  • Improved sugar acid ratios means that, where it is possible to take a quantitative measurement, the yield of a product of the respective plant is increased by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without application of the present invention. According to the present invention, it is preferred that the yield be increased by at least 0.5%, more preferred at least 1 %, even more preferred at least 2%, still more preferred at least 4%, preferably 5% or even more.
  • composition can be in the form of concentrates which are diluted prior to use, although ready-to-use compositions can also be made.
  • the final dilution is usually made with water, but can be made instead of, or in addition to, water, with, for example, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
  • Dustable powders may be prepared by mixing the active ingredients of the composition with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-/sopropyl- and tri-/sopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • compositions may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • the compositions are generally applied at a rate of from 1 to 2000 g/ha, especially from 5 to 1000 g/ha.
  • the rate of application is generally between 0.0005 and 150g per 100kg of seed.
  • Particularly preferred crops are soy, wheat and corn.
  • compositions may be made by the methods described in WO2016/128317 and WO2018/007217, the contents of which are incorporated herein in their entirety.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne la combinaison de dérivés sulfonamides qui sont des agonistes ABA et d'au moins un autre principe actif choisi dans le groupe constitué par les fongicides/bactéricides, les insecticides/acaricides et les régulateurs de croissance des plantes. La combinaison est généralement sous la forme d'une composition comprenant simultanément ces composants utilisée pour contrôler la croissance de plantes, améliorer la tolérance des plantes au stress abiotique (notamment les stress environnementaux et chimiques), inhiber la germination des semences et/ou protéger une plante contre les effets phytotoxiques de produits chimiques, et pour lutter contre les parasites des plantes, en particulier les insectes et/ou les champignons.
PCT/EP2019/085721 2018-12-19 2019-12-17 Compositions de régulation de la croissance des plantes WO2020127319A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1820729.0 2018-12-19
GBGB1820729.0A GB201820729D0 (en) 2018-12-19 2018-12-19 Plant growth regulator compositions

Publications (1)

Publication Number Publication Date
WO2020127319A1 true WO2020127319A1 (fr) 2020-06-25

Family

ID=65147104

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/085721 WO2020127319A1 (fr) 2018-12-19 2019-12-17 Compositions de régulation de la croissance des plantes

Country Status (2)

Country Link
GB (1) GB201820729D0 (fr)
WO (1) WO2020127319A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022204363A1 (fr) * 2021-03-25 2022-09-29 The United States Of America, As Represented By The Secretary Of Agriculture Régulateurs de germination/fleurissement et de mûrissement de fruits
RU2788530C1 (ru) * 2022-05-24 2023-01-23 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный аграрный университет имени И.Т. Трубилина" Применение 6-(4,7-диметокси-1,3-бензодиоксол-5-ил)-4-(4-метоксифенил)-2-тиоксо-1,2-дигидропиридин-3-карбонитрила в качестве средства для активации прорастания семян пшеницы

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050137228A1 (en) * 2003-05-14 2005-06-23 Du Daniel Y. Benzyl sulfonamide derivatives
US20060063799A1 (en) * 2004-09-23 2006-03-23 Gilligan Paul J Sulfonamide bicyclic compounds
WO2013148339A1 (fr) * 2012-03-30 2013-10-03 The Regents Of The University Of California Composés synthétiques pour réponses aba végétatives
WO2016128317A1 (fr) 2015-02-09 2016-08-18 Syngenta Participations Ag Composés 2-oxo-3,4-dihydroquinoléine à utiliser en tant que régulateurs de croissance des plantes
WO2018007217A1 (fr) 2016-07-05 2018-01-11 Syngenta Participations Ag Composés régulateurs de croissance végétale
WO2018017490A1 (fr) * 2016-07-18 2018-01-25 The Regents Of The University Of California Quinabactine de carbamate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050137228A1 (en) * 2003-05-14 2005-06-23 Du Daniel Y. Benzyl sulfonamide derivatives
US20060063799A1 (en) * 2004-09-23 2006-03-23 Gilligan Paul J Sulfonamide bicyclic compounds
WO2013148339A1 (fr) * 2012-03-30 2013-10-03 The Regents Of The University Of California Composés synthétiques pour réponses aba végétatives
WO2016128317A1 (fr) 2015-02-09 2016-08-18 Syngenta Participations Ag Composés 2-oxo-3,4-dihydroquinoléine à utiliser en tant que régulateurs de croissance des plantes
WO2018007217A1 (fr) 2016-07-05 2018-01-11 Syngenta Participations Ag Composés régulateurs de croissance végétale
WO2018017490A1 (fr) * 2016-07-18 2018-01-25 The Regents Of The University Of California Quinabactine de carbamate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"the Manual on Development and Use of FAO Specifications for Plant Protection Products", 1999

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022204363A1 (fr) * 2021-03-25 2022-09-29 The United States Of America, As Represented By The Secretary Of Agriculture Régulateurs de germination/fleurissement et de mûrissement de fruits
RU2788530C1 (ru) * 2022-05-24 2023-01-23 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный аграрный университет имени И.Т. Трубилина" Применение 6-(4,7-диметокси-1,3-бензодиоксол-5-ил)-4-(4-метоксифенил)-2-тиоксо-1,2-дигидропиридин-3-карбонитрила в качестве средства для активации прорастания семян пшеницы

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GB201820729D0 (en) 2019-01-30

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