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WO1989011794A1 - Inhibiteur de la croissance de plantes - Google Patents

Inhibiteur de la croissance de plantes Download PDF

Info

Publication number
WO1989011794A1
WO1989011794A1 PCT/JP1989/000539 JP8900539W WO8911794A1 WO 1989011794 A1 WO1989011794 A1 WO 1989011794A1 JP 8900539 W JP8900539 W JP 8900539W WO 8911794 A1 WO8911794 A1 WO 8911794A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
phenyl
production example
nmr
growth
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/JP1989/000539
Other languages
English (en)
Japanese (ja)
Inventor
Hirosuke Yoshioka
Keido Ko
Myoka Ko
Rinkei Ko
Michi Ko
Hiroshi Ko
Makoto Shimizu
Yuko Nakahara
Ikuko Inoue
Yasuo Kamuro
Toshihito Kakiuchi
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.)
Fujisawa Pharmaceutical Co Ltd
RIKEN
Original Assignee
Fujisawa Pharmaceutical Co Ltd
RIKEN
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 Fujisawa Pharmaceutical Co Ltd, RIKEN filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of WO1989011794A1 publication Critical patent/WO1989011794A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof

Definitions

  • the present invention uses a specific olebamate compound as an active ingredient, suppresses the growth of axillary buds of tobacco and soybeans, improves the yield and quality of tobacco leaves and soybeans, or suppresses the growth of barley.
  • the present invention relates to a growth inhibitor capable of preventing lodging by wind or the like.
  • Maleic acid hydrazide compounds are widely used as plant growth regulators.
  • Japanese Patent Publication No. 50-16641 is disclosed.
  • plant growth regulators based on leubamate as disclosed in U.S. Pat. No. 6,064,098, which are used as herbicides or plant growth inhibitors to suppress the growth of whole plants, especially plant height. Has been put to practical use.
  • the present invention has been made in view of such a situation, and an object thereof is to develop a novel compound and a plant growth inhibitor having excellent performance as a plant growth inhibitor. In particular, it exerts an excellent effect as an axillary bud inhibitor that effectively suppresses the generation or growth of axillary buds without inhibiting the growth of the main branches and stems of tobacco and soybeans, fruits and green leaves It is an object of the present invention to provide an axillary bud inhibitor that can increase the quality and yield of the axillary bud. Another object of the present invention is to provide a growth inhibitor capable of suppressing the growth of cereals such as barley and preventing its lodging.
  • the present invention also relates to a plant growth inhibitor comprising a carbamate compound represented by the following formula [I] as an active ingredient.
  • a plant growth inhibitor comprising a carbamate compound represented by the following formula [I] as an active ingredient.
  • R 1 may be substituted with one or more halogen atoms or methyl groups, a methyl group or hydrogen, R 2 or more with a nitrogen atom or a methyl group. substituted methylation group, R 3 Ho hydrogen or halogen, R 4 is hydrogen, halo gen, main butoxy group or one or more eight androgenic a methyl group substituted by atom, a represents s phenyl group, a husband.
  • the compound [I] also includes a compound represented by the following formula [Ia], more specifically, a compound represented by the following formula [Ib]:
  • the compound represented by the formula has an excellent effect as an axillary bud inhibitor, and for example, in the cultivation of tobacco and the like, it can be applied to the early stage of flowering and the like to obtain branches and leaves. Effectively suppresses the development or growth of axillary buds without causing phytotoxicity, etc., to improve leaf quality and yield, or to improve the quality and yield of fruits, beans, cereals, cotton, etc. It contributes to the growth of barley and the like, and has an excellent effect of preventing lodging. [la]
  • R la and R 2a are the same or different and each represents a methyl group substituted with 1 or 2 halogen atoms
  • Halogen includes fluorine, chlorine, bromine and iodine.
  • “Lower alkyl group” means a straight or branched chain saturated lower aliphatic hydrocarbon residue; preferable examples are, for example, methyl, ethyl, propyl, isobrovir Butyl, isobutyl, tertiary butyl, benzyl, hexyl and the like.
  • “Lower alkoxy group” means a straight-chain or branched group through oxygen.
  • a group attached to a branched saturated lower aliphatic hydrocarbon residue is preferred, such as methoxy, ethoxy, broboxy, isopropoxy, butoxy, a. Sobutoxy, tertiary butoxy, ventiloxy, hexyloxy and the like can be mentioned.
  • R 1 , R 2 , R 3 , R 4 and A correspond to R 1 to R 4 , R la to R 2a and A in the general formulas [I] and [la], respectively. is there.
  • the compound of the formula [Ib] corresponds to the compound of “Compound No. 8” in the following table.
  • C II b] and a compound represented by the following general formula [III], [Ilia] or [IIIb] are equimolar amounts of triethylamine, pyridin and the like. It can be obtained by reacting in the presence of.
  • R 1 , R la , R 2 , and R 2a have the same meanings as described above.
  • the above reaction is performed for toluene, tetrahydrofuran, ether, dichloromethane, pyridine, etc. As described above, the reaction is carried out in a solvent which does not adversely affect the progress of the reaction or under heating.
  • the compounds represented by the above general formulas [I], [la], and [lb] have a specific effect as a growth inhibitor during plant cultivation, in particular, the inhibition of axillary bud formation or growth. Its application to tomatoes, beans, cotton, cereals, tobacco, fruit trees, greening trees, etc. significantly reduces the occurrence or growth of axillary buds, Contributes to quality improvement and yield improvement of beans, cotton, tobacco leaves, etc. In addition, it exerts an excellent effect on suppressing the growth of cereals such as barley and preventing lodging by wind and the like.
  • the application period depends on the target plant. For example, in the case of tobacco, it is most effective to apply it immediately after pinching, and it is better to spray it when the grain has a sufficient number of effective stems.
  • the appropriate concentration at the time of use depends on the type of the target plant, but it is usually used after being diluted to about 100 to 1000 ppm, preferably to 500 to 300 ppm.
  • the plant growth regulator of the present invention can be mixed with various carriers according to the scene of use, and used as, for example, powders, granules, tablets, wettable powders, emulsions and the like.
  • the carrier here may be a liquid or a solid, and a combination thereof is also possible.
  • various adjuvants used in the preparation of agricultural chemicals for example, a spreading agent, an emulsifier, and the like can be added as necessary.
  • any of the preparations can be used alone as it is, or can be used as a mixture with insecticides, fungicides, herbicides, other plant growth regulators, or fertilizers. .
  • Double line, lH, J 7.2Hz), 6.42 to 6.80 (b, lH), 690 to 7.52 (m, 5H)
  • Axillary bud inhibitor Axillary bud total growth weight of each up to 9 axillary buds (era)
  • Axillary bud inhibitor Elongation amount of each of up to 9 axillary buds (era) Axillary bud total fresh weight
  • Axillary bud inhibitor Elongation amount of each of up to 9 axillary buds (cm) Axillary bud Total live weight
  • a 300 ppm and a 100 ppm emulsified solution of Compound No. 26 were prepared as the agent of the present invention, and a C-MH agent (trade name, manufactured by Nippon Hydrazine Industry Co., Ltd.) was used as a comparator.
  • H) Prepare a 100-fold solution of a 58% solution of.
  • Tsukuba No. 1 One tobacco (Tsukuba No. 1) is planted in a 1/5000 are Wagner bot and grown at room temperature. In the bud stage (late September), the above drug is sprayed on the leaf base in 10 strains of each section on the day. Every 10 days after spraying, axillary buds that had grown to a length of at least 10 cm (length to the tip of the leaf) were collected, and their number and fresh weight were examined.
  • One tobacco (cultivar: Tsuguba No. 1) is planted in a 1/500 arepot and grown at room temperature. On the day of core removal, 300 ml of an emulsified solution of each compound shown in Table 3 below was sprayed at a rate of 15 ml per strain according to the usual spray method of a C-MH agent.
  • the results are as shown in Table 3.
  • the agent of the present invention exhibited an axillary bud inhibitory effect comparable to or more than a 100-fold dilution of the comparative agent even at a concentration of 300 ppm. .
  • Test example 4 Barley rod elongation suppression test
  • the growth inhibitor of the present invention is different from the known control agent (Psychocel), and the suitable time for spraying is late, and the booting stage is at the booting stage.
  • the practical concentration is lower than that of Psychocell, and is around 250 ppm.
  • the present invention is constituted as described above and can effectively suppress the generation or growth of axillary buds as a plant growth inhibitor, so that beans, fruits, vegetables, tobacco leaves, barley The quality and yield can be improved by utilizing it for the cultivation of cereals and the like.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Inhibiteur de la croissance de plantes, contenant en tant qu'ingrédient actif un composé de carbamate représenté par la formule générale (I). Cet inhibiteur présente un excellent effet en tant que retardateur de croissance de bourgeons axillaires de tabac ou de soya, et empêche l'orge de verser.
PCT/JP1989/000539 1988-06-07 1989-05-30 Inhibiteur de la croissance de plantes Ceased WO1989011794A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP63/139804 1988-06-07
JP13980488 1988-06-07
JP1/74592 1989-03-27
JP7459289 1989-03-27

Publications (1)

Publication Number Publication Date
WO1989011794A1 true WO1989011794A1 (fr) 1989-12-14

Family

ID=26415756

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1989/000539 Ceased WO1989011794A1 (fr) 1988-06-07 1989-05-30 Inhibiteur de la croissance de plantes

Country Status (1)

Country Link
WO (1) WO1989011794A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104159581A (zh) * 2012-01-06 2014-11-19 阿比德治疗公司 氨基甲酸酯化合物及其制备和使用方法
US9771341B2 (en) 2015-03-18 2017-09-26 Abide Therapeutics, Inc. Piperazine carbamates and methods of making and using same
US9981930B1 (en) 2016-11-16 2018-05-29 Abide Therapeutics, Inc. MAGL inhibitors
US10093635B2 (en) 2016-11-16 2018-10-09 Abide Therapeutics, Inc. MAGL inhibitors
US10450302B2 (en) 2015-05-11 2019-10-22 Lundbeck La Jolla Research Center, Inc. Methods of treating inflammation or neuropathic pain
US10463753B2 (en) 2016-02-19 2019-11-05 Lundbeck La Jolla Research Center, Inc. Radiolabeled monoacylglycerol lipase occupancy probe
US10570106B2 (en) 2018-05-15 2020-02-25 Lundbeck La Jolla Research Center, Inc. MAGL inhibitors
US10899737B2 (en) 2016-09-19 2021-01-26 Lundbeck La Jolla Research Center, Inc. Piperazine carbamates and methods of making and using same
US11702393B2 (en) 2020-04-21 2023-07-18 H. Lundbeck A/S Synthesis of a monoacylglycerol lipase inhibitor

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59190904A (ja) * 1983-04-14 1984-10-29 ピ−ピ−ジ−・インダストリイズ・インコ−ポレイテツド タバコサツカ−の生育抑制組成物およびその生育抑制法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59190904A (ja) * 1983-04-14 1984-10-29 ピ−ピ−ジ−・インダストリイズ・インコ−ポレイテツド タバコサツカ−の生育抑制組成物およびその生育抑制法

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11021453B2 (en) 2012-01-06 2021-06-01 Lundbeck La Jolla Research Center, Inc. Carbamate compounds and methods of making and using same
JP2015508407A (ja) * 2012-01-06 2015-03-19 アビデ セラピューティクス，インク． カルバメート化合物およびその製造および使用
EP2800565A4 (fr) * 2012-01-06 2015-04-29 Abide Therapeutics Inc Composés de carbamate et leur préparation et utilisation
US9133148B2 (en) 2012-01-06 2015-09-15 The Scripps Research Institute Carbamate compounds and of making and using same
AU2013207252B2 (en) * 2012-01-06 2016-06-09 H.Lundbeck A/S Carbamate compounds and pharmaceutical compositions thereof
JP2017125039A (ja) * 2012-01-06 2017-07-20 アビデ セラピューティクス，インク． カルバメート化合物およびその製造および使用
CN104159581B (zh) * 2012-01-06 2017-09-01 阿比德治疗公司 氨基甲酸酯化合物及其制备和使用方法
US12018004B2 (en) 2012-01-06 2024-06-25 H. Lundbeck A/S Carbamate compounds and methods of making and using same
US9957242B2 (en) 2012-01-06 2018-05-01 The Scripps Research Institute Carbamate compounds and methods of making and using same
US11530189B2 (en) 2012-01-06 2022-12-20 H. Lundbecka/S Carbamate compounds and methods of making and using same
CN104159581A (zh) * 2012-01-06 2014-11-19 阿比德治疗公司 氨基甲酸酯化合物及其制备和使用方法
US9994537B2 (en) 2015-03-18 2018-06-12 Abide Therapeutics, Inc. Piperazine carbamates and methods of making and using same
US9771341B2 (en) 2015-03-18 2017-09-26 Abide Therapeutics, Inc. Piperazine carbamates and methods of making and using same
US10450302B2 (en) 2015-05-11 2019-10-22 Lundbeck La Jolla Research Center, Inc. Methods of treating inflammation or neuropathic pain
US11034674B2 (en) 2015-05-11 2021-06-15 H. Lundbeck A/S Methods of treating inflammation or neuropathic pain
US10463753B2 (en) 2016-02-19 2019-11-05 Lundbeck La Jolla Research Center, Inc. Radiolabeled monoacylglycerol lipase occupancy probe
US10899737B2 (en) 2016-09-19 2021-01-26 Lundbeck La Jolla Research Center, Inc. Piperazine carbamates and methods of making and using same
US10093635B2 (en) 2016-11-16 2018-10-09 Abide Therapeutics, Inc. MAGL inhibitors
US9981930B1 (en) 2016-11-16 2018-05-29 Abide Therapeutics, Inc. MAGL inhibitors
US10570106B2 (en) 2018-05-15 2020-02-25 Lundbeck La Jolla Research Center, Inc. MAGL inhibitors
US11214557B2 (en) 2018-05-15 2022-01-04 H. Lundbeck A/S MAGL inhibitors
US11332453B2 (en) 2018-05-15 2022-05-17 H. Lundbeck A/S MAGL inhibitors
US11702393B2 (en) 2020-04-21 2023-07-18 H. Lundbeck A/S Synthesis of a monoacylglycerol lipase inhibitor

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