[go: up one dir, main page]

WO1991013880A1 - Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances - Google Patents

Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances Download PDF

Info

Publication number
WO1991013880A1
WO1991013880A1 PCT/SU1990/000067 SU9000067W WO9113880A1 WO 1991013880 A1 WO1991013880 A1 WO 1991013880A1 SU 9000067 W SU9000067 W SU 9000067W WO 9113880 A1 WO9113880 A1 WO 9113880A1
Authority
WO
WIPO (PCT)
Prior art keywords
urea
dimethylamine
salt
sulfonyl
compound
Prior art date
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.)
Ceased
Application number
PCT/SU1990/000067
Other languages
English (en)
Russian (ru)
Inventor
Vladimir Iosifovich Sorokin
Galina Vladimirovna Kuznetsova
Natalya Ionovna Rusakova
Ljubov Alexandrovna Tsybalova
Irina Nikolaevna Melikhova
Tatyana Evgenievna Granina
Viktor Nikolaevich Drozd
Alexandr Alexeevich Shapovalov
Nelli Pavlovna Loi
Tatyana Anatolievna Shvareva
Angelina Alexandrovna Petunova
Julian Dmitrievich Khomlyak
Nikolai Sidorovich Kravchenko
Vladimir Vladimirovich Mily
Vyacheslav Alexeevich Barashkin
Margarita Mikhailovna Frolova
Vladimir Pavlovich Bezsolitsen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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
Priority to PCT/SU1990/000067 priority Critical patent/WO1991013880A1/fr
Priority to CH3286/91A priority patent/CH683341A5/de
Priority to AU68891/91A priority patent/AU631474B2/en
Priority to DE19904092524 priority patent/DE4092524T/de
Priority to JP3500742A priority patent/JPH05501415A/ja
Priority to DE4092524A priority patent/DE4092524C2/de
Application filed by Individual filed Critical Individual
Priority claimed from CA002036334A external-priority patent/CA2036334C/fr
Priority to CA002036334A priority patent/CA2036334C/fr
Priority to CS91442A priority patent/CS44291A3/cs
Priority to HU91598A priority patent/HU207789B/hu
Priority to FR9102282A priority patent/FR2673181B1/fr
Priority to CN91102096.9A priority patent/CN1064388A/zh
Publication of WO1991013880A1 publication Critical patent/WO1991013880A1/fr
Priority to GB9123657A priority patent/GB2251613B/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the predominant level of technology is 10.
  • An important issue in the agricultural sector is the extension of the crop. For this purpose, we use stimulating substances and herbicides.
  • ⁇ - / 2-chloro-benzene sulfonyl-3- / 4-methyl-6-methoxy- ⁇ , 3,5-20-thiazin-2-yl / urea compound is known.
  • the product is used on the basis of the aforementioned connection in the agricultural sector to protect the crops of wheat, barley, wheat, wheat and flax, so that there is only 4 crops.
  • Substances are also known, possessing, for all of them, 25 cidal activity activity of the plant growth regulator. As a matter of fact, the effect of these substances is compatible with the resultant, stable or formative effects.
  • These compounds are derived from general aromatic sulfate urea of the general formula
  • Such compounds in the dose of 60-400 g / ha exhibit damaging properties and possess a standard, stable or formative effect (P5, ⁇ , 4231784).
  • well-known compounds inhibit the growth of cultivated plants.
  • the claimed compounds are new and have not been described in the literature.
  • the basic task of the invention is to create new compounds having a stimulating activity with a simultaneous herbicidal effect.
  • the claimed compounds possess a stimulating and active activity. - 3
  • the claimed invention is, according to the invention, preferably contains Georgia-styrene-sulfide-dimethyl-amine-3- / 4-amine-active material.
  • the claimed invention may also be predominantly contained in the material, ⁇ - / 2-coolant-benzyl /--- --2- thiazine-2-yl / urea or its potassium, sodium or diethyl ethanolamine salt of the following formula:
  • the claimed funds possess high activity and are used to stimulate and inhibit the growth of plants. 5 Better embodiment of the invention Declared new compounds - substituted phenyl-sulphonylureas urea - are substances which are highly resistant to white matter.
  • Declared substituted phenylsulfonyl-iazinyl-urea the interaction of substituted benzene-sulfonyl isocyanates with substituted 2-amine- ⁇ , 3,5- ⁇ -chazines
  • ⁇ 1 c ⁇ , ⁇ 2 , ⁇ ntended 3 ;
  • reaction mass is reduced to 20 ° 0 5 and the mixture is stirred for another 2 hours before the complete completion of the reaction.
  • the plant is filtered, washed with a distributor, and the reaction and dried.
  • the claimed compounds may also be obtained by the reaction of a substituted arylsulfonamide with a diluted 10-nylisocyanate and a substituted 2-amine, 3,5-thiazole in a 60
  • ⁇ 1 c ⁇ , ⁇ 2 , ⁇ ntended 3 ;
  • ⁇ ⁇ 0 ⁇ 3 , - ⁇ 2 ⁇ 5 ' ⁇ 6 % ' s ⁇ n ⁇ ⁇ -2.
  • thermocamethylsilane Taken on the "ta -250" unit in the operation with the use of a thermocamethylsilane as a part of the internal standard. ⁇ Brass As an example, P ⁇ -sectect ⁇ - / 2-l ⁇ -
  • the claimed salts result in the interaction of substituted phenylsulfonyl ureasinyl ureas with alkali hydroxide.
  • Sites I have taken on the “ha -250” unit with a frequency of + 250.13 MHz.
  • the claimed compounds are active substances for stimulating and inhibiting the growth of plants.
  • the effectiveness of the claimed compounds and devices are dependent on
  • the claimed compounds have the property of substantially accelerating the growth of cultural plants in the process of phangiogenesis, which leads to phytogenesis.
  • the inventive device is intended for the treatment of green plants, soil and soil, methods
  • the inactive mixture is heated for 3 hours at a temperature of 95 -00 ° C, cooled and added 11.2 g / 0.05 mol / 2-amino-4-dimethylamine-6-isopropyl-di-iminazinase; the mixture is heated for 3 hours at a temperature of 50-60 ° C, it is cooled, the precipitate is filtered, it is 10 yt and it is produced 17.0 g / 80 / of compound I, mp. 184-186 ° C / from acetone /.
  • the effective weight of 25 is stirred for 3 hours at a temperature of 60-70 ° C, and then 2 hours at a room temperature.
  • Additives are pre-washed, washed with benzene, dried and obtained 36.5 g / 95 $ / ⁇ - / 2-chlorobenzene sulfenyl / -3- / 4-dimethylamine-6- -isopropyl-imidene-imidene-2-imidene / urea, 30 T..pl. ⁇ 84- ⁇ 86 ° C.
  • the data of the elemental analysis are identical to those given in Example I.
  • the mixture is heated to a temperature of 50-60 ° C and add 2.15 g / 0.0099 mol / 2-chlorobenzene sulfonylation.
  • the active mixture is stirred for 2 hours at a temperature of 5 ° at 60 ° C and 2 hours at a temperature of 20 ° C, the precipitate is filtered and supplied with 4.0 g / 95 $ / s. 172-173 ° C (with ⁇ pl.).
  • Example 19 from sodium hydroxide and ⁇ - / 2-10 - ⁇ lobenzene sulphonyl / -3- / 4-dimethylamine-6-methyl) ⁇ -lidenimine oxy-2, 3,5- ⁇ iliazin-2 a salted salt with an output of $ 92 T..pl. ⁇ 6 ⁇ ° ⁇ / ⁇ schreib. /.
  • Methyl salt of ⁇ - / 2-chlorobenzene sulfonyl / -3- / 4-dimethylamino-6-benzylidenimine oxy- ⁇ , 3,5- ⁇ iazin-2-yl / urea (compound 20). 20 similar to example 19 from hydrous oxide and
  • Methyl salt of ⁇ - / 2-methoxycarbonyl benzene-phenyl / -3-G4-Dimethylamine-6- / ⁇ -methyl / ⁇ ylidenimine-oxy- ⁇ , 3,5- ⁇ iazin-2-yl) urea (26).
  • Example 19 from sodium hydroxide and ⁇ - / 2-methoxybenylbenzene sulfonyl / -3- 4-dimethyl-amino-6 -, / ⁇ ⁇ . -labeled / ⁇ ilidenigline oxy-1,3,5- ⁇ iazin--2-yl] urea receive the above salt, yield $ 92, ⁇ .pl. ⁇ 5 ⁇ ° 0 / ⁇ ml./.
  • Example 19 from sodium hydroxide and ⁇ - / 2-methoxypropylbenzene sulphonyl / -3- [4-dimethylamino-6- / 2- ⁇ l / ⁇ -benzylidene-amine-3,5-amine, 2- the above salt, exiting $ 95, ⁇ .pl. 15 ⁇ 57 ° 0 / ⁇ ml./.
  • Analogous example 19 from sodium hydroxide and ⁇ - / 2,5-dichlorobenzene sulphonyl / -3- / 4-dimethylamino-6- is reduced-oxidized, 1,3,5- ⁇ thiazin-2-yl / urea, , ⁇ . ⁇ . ⁇ 74 ° 0 / ⁇ azl. /. Found, $: C 42.86; ⁇ 3.01; 01 13.35;
  • Carbonate salt of ⁇ - / 2-hydroxybenzene sulfonyl / -3- / 4-methyl-6-isopropylidene, 1, 3, 5-thiazin-2-yl / urea (compound 35).
  • the active mixture is stirred at a temperature of 30 to 40-45 ° 0 for 3 hours before the dissolution of sulfonylurea.
  • Carbonate salt of jointly- / 2-methoxybenzenesulfonyl phenyl / -3- [4-dimethylamine-6-G2-hydroxybenzhenimine-15 ⁇ oxy- ⁇ , 3,5- ⁇ iazin-2-yl] urea (compound 45).
  • Diethylamine ammonium salt ⁇ - / 2-chloro-benzensul-phenyl / -3- / 4-dimethylamino-6-isopropylphenidenimin oxy-1,3, 5-thiazin-2-yl / urea (compound 52).
  • bathroom salt which is a self-contained oil plant, with an output of $ 94.5.
  • Analogous example 53 from diethylethanolamine and ⁇ - / 2-hydroxybenzene sulfonyl / -2- [4-dimethyl-tylamino-6- (2-carbonyl-benzylidenimine oxy-1, 3, 5-methylazole] , which is a self-contained oil sediment, with an output of $ 96.
  • Analogous example 53 of diethylethanolamine and ⁇ - / 2-methoxybenyl enensyl sulfonyl / -3- / 4-dimethylamine-6-benzene-reduced-1, 3-5-methylazole which is a self-contained oil 25th plant, with a yield of $ 94.5.
  • Chevins receive the aforementioned salt, which is a special oil plant, with an output of 93.
  • Results 5 are presented in table 6 as a% to the control panel (without processing of mail).
  • the weight of the land mass was 136 $ for sale (up to 50 g / ha).
  • the effect of these compounds was to suppress in the long-term degree the same as the two-year-olds, and also the malicious people.
  • the use of session 53 at a dose of 20 g / ha resulted in an increase in the yield of green mass.
  • Compound 53 in the form of a one-off-the-main plant was mentioned in terms of income brought in doses of 10 and 20 g / ha
  • the accounting area is 36 m, and the return is 4-fold.
  • the main host species of foreign plants in the foreign sector are: bristles, white mother, a single
  • Standard GZHN - 2.1 kg / ha (crop at 25 kg / ha, ⁇ ⁇ 5 - 4.0 kg / ha).
  • compound 53 caused the death of $ 42 and 58 species with a yield of 0 g / ha 5 and 20 g / ha, respectively.
  • the gain was 0.5 kg / ha and 5.2 kg / ha, respectively.
  • the claimed compounds are displaced phenylsulfonylazinous and they are also involved in the 5 substances of the claimed funds for the stimulation and the reduction of welfare.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Phénylsulfonyltriazinylurée substituée, et ses sels, de formule (I), dans laquelle R1 est Cl, NO¿2?, COOCH3; R?2¿ est H, Cl; R3 est H, CH¿3; R?4 est CH¿3?, C2H5, C6H5, C6H4Cl-2 et X est absent ou X est K, Na, α. L'agent revendiqué, destiné à stimuler ou supprimer la croissance des plantes, contient comme substance active de la phénylsulfonyltriazinylurée substituée ou ses sels, de formule indiquée ci-dessus.
PCT/SU1990/000067 1990-03-07 1990-03-07 Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances Ceased WO1991013880A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
PCT/SU1990/000067 WO1991013880A1 (fr) 1990-03-07 1990-03-07 Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances
CH3286/91A CH683341A5 (de) 1990-03-07 1990-03-07 Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel zur Stimulation und Unterdrückung des Pflanzenwachstums auf deren Grundlage.
AU68891/91A AU631474B2 (en) 1990-03-07 1990-03-07 Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them
DE19904092524 DE4092524T (fr) 1990-03-07 1990-03-07
JP3500742A JPH05501415A (ja) 1990-03-07 1990-03-07 置換フェニルスルホニルトリアジニル尿素、その塩並びにそれに基づく植物成長促進及び阻害用薬剤
DE4092524A DE4092524C2 (de) 1990-03-07 1990-03-07 Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel mit pflanzenwachstumsregelierender Wirkung
CA002036334A CA2036334C (fr) 1990-03-07 1991-02-14 Derives de substitution de phenylsulfonyltriazinylurees; leurs sels et agents a base de ces composes pour la stimulation ou l'inhibition de la croissance des plantes
CS91442A CS44291A3 (en) 1990-03-07 1991-02-20 Agent for plant growth promoting and inhibiting
HU91598A HU207789B (en) 1990-03-07 1991-02-22 Composition for controlling growth of plants containing phenyl-sulfonyl-triazine-urea derivatives as active components
FR9102282A FR2673181B1 (fr) 1990-03-07 1991-02-26 Phenylsulfonyltriazinyl-urees substituees, leurs sels et produit les contenant pour stimuler et inhiber la croissance des plantes.
CN91102096.9A CN1064388A (zh) 1990-03-07 1991-03-05 用于促进和抑制植物生长的制剂
GB9123657A GB2251613B (en) 1990-03-07 1991-11-07 Substituted phenylsulphoryltrianzinyl ureas, salts thereof and agent for plant growth stimulation and inhibition based thereon

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
PCT/SU1990/000067 WO1991013880A1 (fr) 1990-03-07 1990-03-07 Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances
CA002036334A CA2036334C (fr) 1990-03-07 1991-02-14 Derives de substitution de phenylsulfonyltriazinylurees; leurs sels et agents a base de ces composes pour la stimulation ou l'inhibition de la croissance des plantes
CS91442A CS44291A3 (en) 1990-03-07 1991-02-20 Agent for plant growth promoting and inhibiting
CN91102096.9A CN1064388A (zh) 1990-03-07 1991-03-05 用于促进和抑制植物生长的制剂

Publications (1)

Publication Number Publication Date
WO1991013880A1 true WO1991013880A1 (fr) 1991-09-19

Family

ID=27426838

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1990/000067 Ceased WO1991013880A1 (fr) 1990-03-07 1990-03-07 Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances

Country Status (1)

Country Link
WO (1) WO1991013880A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009419A1 (fr) * 1978-09-27 1980-04-02 E.I. Du Pont De Nemours And Company Sulfonamides pour l'agriculture, leur préparation et leur utilisation
US4348219A (en) * 1980-07-11 1982-09-07 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
DE3322280A1 (de) * 1983-06-16 1985-01-03 Schering AG, 1000 Berlin und 4709 Bergkamen Substituierte sulfonylharnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwuchsregulierender wirkung
EP0164269A2 (fr) * 1984-06-07 1985-12-11 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
US4786316A (en) * 1984-07-13 1988-11-22 E. I. Du Pont De Nemours And Company Herbicidal ortho-sulfamoyl sulfonamides
WO1989009214A1 (fr) * 1988-03-24 1989-10-05 E.I. Du Pont De Nemours And Company Fluoroalkoxy-aminotriazines permettant de maitriser la croissance de mauvaises herbes dans les plants de betteraves sucrieres

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009419A1 (fr) * 1978-09-27 1980-04-02 E.I. Du Pont De Nemours And Company Sulfonamides pour l'agriculture, leur préparation et leur utilisation
US4348219A (en) * 1980-07-11 1982-09-07 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
DE3322280A1 (de) * 1983-06-16 1985-01-03 Schering AG, 1000 Berlin und 4709 Bergkamen Substituierte sulfonylharnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwuchsregulierender wirkung
EP0164269A2 (fr) * 1984-06-07 1985-12-11 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
US4786316A (en) * 1984-07-13 1988-11-22 E. I. Du Pont De Nemours And Company Herbicidal ortho-sulfamoyl sulfonamides
WO1989009214A1 (fr) * 1988-03-24 1989-10-05 E.I. Du Pont De Nemours And Company Fluoroalkoxy-aminotriazines permettant de maitriser la croissance de mauvaises herbes dans les plants de betteraves sucrieres

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
L.T. MAKEEVA-GURYANOVA et al., "Sulfonilmocheviny-novye Perspektivnye Gerbitsidy", 1989, VNIITEI AGROPROM, (Moscow), pages 5, 6, 11. *

Similar Documents

Publication Publication Date Title
US2562011A (en) Herbicidal compositions and application thereof
CN1222828A (zh) 除草混合物
CZ283491B6 (cs) Synergický mikrobicidní a fungicidní prostředek Synergický mikrobicidní fungicidní prostře
BG60302B2 (bg) Хербицидно средство и метод за борба с нежелана растителност
RU2029471C1 (ru) Производные пиримидина, гербицидная композиция и способ борьбы с сорняками с использованием композиции
EA015243B1 (ru) Способ повышения урожайности кукурузы
EA015804B1 (ru) Синергически действующие и хорошо переносимые культурными растениями гербицидные средства, которые содержат гербициды из группы бензоилпиразолов
JPH0759411A (ja) 亜燐酸又はその塩の１種を使用する種子処理及びこうして処理した種子
EA019698B1 (ru) Способ борьбы с сорняками и гербицидная композиция
PL117589B1 (en) Plant growth regulator
WO2020262612A1 (fr) Agent de lutte contre les maladies des plantes et procédé de lutte contre les maladies des plantes
DE2646406A1 (de) Pflanzenwuchsregler
JPH06239709A (ja) Ｓ−ベンジルチオールカーバメートおよびその稲田における雑草抑制剤としての使用
JPS6254108B2 (fr)
WO1991013880A1 (fr) Phenylsulfonyltriazinyluree substituee, et ses sels, et agent de stimulation et de suppression de la croissance des plantes a base de ces substances
EA000532B1 (ru) Гербицидная композиция, содержащая 4-бензоилизоксазол и аклонифен
US3201220A (en) Herbicidal composition and method
US4509974A (en) S-n-Butyl-N,N-diisopropyl thiocarbamate as a selective herbicide in cotton
SU519109A3 (ru) Фунгицидное средство
US4028091A (en) Herbicidal composition
SU530628A3 (ru) Гербицидное средство
US4582528A (en) S-methyl-N,N-diethyl thiocarbamate as a selective herbicide in rice
US2536751A (en) Herbicidal compositions
WO2025078992A1 (fr) Procédé de lutte contre les mauvaises herbes
JP2767128B2 (ja) 除草剤組成物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU CH DE GB JP US

RET De translation (de og part 6b)

Ref document number: 4092524

Country of ref document: DE

Date of ref document: 19920423

WWE Wipo information: entry into national phase

Ref document number: 4092524

Country of ref document: DE