WO2006136073A1 - Composés herbicides de type benzoxazine n-substituée par un groupe carboxyle - Google Patents

Composés herbicides de type benzoxazine n-substituée par un groupe carboxyle Download PDF

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Publication number
WO2006136073A1
WO2006136073A1 PCT/CN2006/000691 CN2006000691W WO2006136073A1 WO 2006136073 A1 WO2006136073 A1 WO 2006136073A1 CN 2006000691 W CN2006000691 W CN 2006000691W WO 2006136073 A1 WO2006136073 A1 WO 2006136073A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
fluoro
dihydrobenzo
isoindole
tetrahydro
Prior art date
Application number
PCT/CN2006/000691
Other languages
English (en)
Chinese (zh)
Inventor
Mingzhi Huang
Yeguo Ren
Manxiang Lei
Aiping Liu
Xiaoming Ou
Lu Huang
Jing Ren
Li Hu
Zhongke Hou
Xiaoguang Wang
Original Assignee
Hunan Research Institute Of Chemical Industry
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 Hunan Research Institute Of Chemical Industry filed Critical Hunan Research Institute Of Chemical Industry
Priority to JP2008517296A priority Critical patent/JP4838306B2/ja
Publication of WO2006136073A1 publication Critical patent/WO2006136073A1/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
    • A01N43/84—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 1,4
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • N-carboxylic acid derivative substituted benzoxazine compound having herbicidal activity N-carboxylic acid derivative substituted benzoxazine compound having herbicidal activity
  • the present invention relates to a herbicidal N-carboxylic acid derivative-substituted benzoxazine compound, a process for the preparation thereof and use thereof as a herbicide.
  • EP420194, USP 4,640, 707, USP 5,508, 084, USP 5, 127, 935, USP 5, 232, 835, USP 6, 632 154, DE 392 207, JP 03, 47180, USP 5,232, 098, JP 62, 277 383, EP 362 615, etc. have reported many heterocyclic tetrasubstituted benzene compounds and their complexes having herbicidal activity. Among them, the change of the N-substituent on the benzoxazine ring has a great influence on the biological activity, selectivity and crop safety of the compound. There are currently no reports of benzoxazine ring compounds substituted with N-carboxylic acid derivatives.
  • the chemical structure of such compounds is represented by the structural formula (I):
  • X is hydrogen, halogen, sulfhydryl, methyl, optimally gas
  • Y is oxygen, NH, and most preferably oxygen;
  • R 1 is hydrogen, halogen, methyl, phenyl, most preferably hydrogen or methyl;
  • R 2 is (dC 4 )alkyl, (d-)nonyloxy, preferably methyl or ethyl;
  • R 3 , R 4 are the same or different hydrogen, (C "C 8 ) fluorenyl, phenyl, halophenyl, and most preferably R 3 is hydrogen or methyl, R 4 is methyl or phenyl;
  • R m is a mono- or poly-substituted, the same or different hydrogen, (dC 4 ) fluorenyl, nitro, fluoro, chloro, bromo, iodo, etc., wherein m represents the number of substituents, optionally 1, 2, 3 Or 4, the optimal R m is hydrogen or fluorine.
  • the preparation method of the present invention is as follows:
  • the intermediate (A) can be synthesized by the method described in the document US Pat. No. 4,734,124.
  • the compound (( ⁇ or ( 2 ) is added with an acid binding agent and a halogenated carboxylic acid ester (or 1) 2 in a suitable solvent for several hours to obtain an ester target compound ( ⁇ or), wherein the preferred solvent is DMF,
  • a good acid binding agent is potassium carbonate.
  • the excellent reaction time is 8 hours.
  • the present invention provides a part of the compound of the formula (I) and the physicochemical properties thereof, as shown in Table 1.
  • the compound of the general formula of the present invention After biological screening, the compound of the general formula of the present invention has very good herbicidal activity, and the herbicidal activity of some compounds is superior to the conventional herbicide currently used, and the pre-emergence soil treatment or 7.5 ga at a dose of 15 ga.i/ha. At the dose of i/ha, the stem and leaf treatment after seedlings is 90% effective against most broad-leaved weeds, and also has some control effect on some monocotyledonous weeds. One or more of corn, wheat, peanuts, etc. Crop safety.
  • Example 1 2-(7-Fluoro-6-(5-methyl-1,3-dioxoisoindol-2-yl)-3-oxo-2,3-dihydrobenzo Cb] [1 , 4] Preparation of ethyl oxazide-4-yl)propionate (Compound E1 - 08 in Table 1).
  • Example 2 2-(6-(1,3-Dioxy-4,5,6,7-tetrahydro-1H-isoindole-2(3H)-yl)-7-fluoro-3-oxo- Preparation of 2,3-dihydrobenzo[b][1,4]oxazin-4-yl)acetate (Compound E2-04 in Table 1).
  • Example 3 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindole-2(3H)-yl)-7-fluoro-3-oxy-2 , 3_Dihydrobenzo[b][1,4]oxazin-4-yl) N-methylacetamide (Compound F2- 01 in Table 1).
  • Table 2 lists some of the compounds of the present invention, such as E2- 01, E2- 02, E2- 04, E2- 05, E2- 08, etc., for inhibiting the pre-emergence soil treatment and post-emergence stem and leaf treatment of potted plants. .
  • the five compounds tested were at a low dose of 7.5 g ai/ha and 15. 0 g ai/ha, and the pre-emergence soil treatment or post-emergence stem and leaf treatment was better for broad-leaved weeds.
  • the control effect also has certain control effect on some monocotyledonous weeds.
  • Application Example 2 Crop safety test.
  • the dicotyledon test material grows to 2 true leaf stage, and the post-emergence stem and leaf are treated with 150, 120, 75, 30, 15, 7.5, 1.5 gai/ha liquid Spray treatment, the seedlings were planted on the next day, and the soil was treated with spray solvent and water, respectively.
  • the test materials were placed in the greenhouse for cultivation, and the symptoms of crop damage were observed 15 days later, and the growth inhibition rate of the shoots was visually observed.
  • Growth inhibition rate (%) 100 (control plant height - treated plant height) I control plant height, estimated crop IC' based on growth inhibition rate, value, combined with weed IC 9 value, calculated by /!: ⁇ Selectivity index (Z), safety grade standard: A: Z 4 ; B: 2 ⁇ Z ⁇ 4; C: 1 Z ⁇ 2 , D: Z ⁇ 1 , Grade B or higher can be regarded as safe.
  • Z Selectivity index
  • E2-05 and E2- 08 are shown in Table 3.
  • Compound E2- 05 was treated at a dose of 15 g ai/ha for rice, wheat, corn, cotton, soybean, etc., at a dose of 7.5 g ai/ha, stem and leaf treatment for wheat, corn Safety.
  • Compound E2-08 was safe for wheat, peanut and other crops at a dose of 37.5 g ai/ha, and stem and leaf treatment was safe for wheat at a dose of 15 g ai/ha.
  • Table 3 Crop Safety Experiment Results

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des composés de type benzoxazine N-substituée par un groupe carboxyle répondant à la formule (I) dans laquelle, Het répond à la formule (II) ou à la formule (III) où : X représente H, un atome d’halogène, CN ou un groupe méthyle ; Y représente O ou NH ; R1 représente H, un atome d’halogène, un groupe méthyle ou phényle ; R2 représente un groupe alkyle en C1 à C4 ou alcoxyalkyle en C1 à C4 ; R3 et R4 représentent H, un groupe alkyle en C1 à C8, phényle ou halogénophényle ; Rm peut être mono- ou poly-substitué, et peut être un groupe identique ou différent choisi parmi H, un groupe alkyle en C1 à C4, NO2 et un atome d’halogène, m représentant le nombre de substituants et peut être choisi parmi 1, 2, 3 et 4. Les composés de la présente application ont d'excellentes activités herbicides, dans le cas d’un traitement du sol avant ensemencement avec un dosage de 15 g ai/ha et d’un traitement des tiges et feuilles après ensemencement avec un dosage de 7,5 g ai/ha, les rapports d’effet herbicide des présents composés sur la plupart des mauvaises herbes à grandes feuilles sont supérieurs ou égaux à 90 %, les présents composés présentent également une certaine efficacité contre quelques mauvaises herbes monocotylédonées et les présents composés sont sans risque pour une ou plusieurs cultures, telles que le maïs, le blé et une arachide, etc.
PCT/CN2006/000691 2005-06-21 2006-04-17 Composés herbicides de type benzoxazine n-substituée par un groupe carboxyle WO2006136073A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008517296A JP4838306B2 (ja) 2005-06-21 2006-04-17 除草活性を有するｎ−カルボン酸誘導体置換ベンゾオキサジン類化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNB2005100317243A CN100387582C (zh) 2005-06-21 2005-06-21 具有除草活性的n-羧酸衍生物取代的苯并噁嗪类化合物
CN200510031724.3 2005-06-21

Publications (1)

Publication Number Publication Date
WO2006136073A1 true WO2006136073A1 (fr) 2006-12-28

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PCT/CN2006/000691 WO2006136073A1 (fr) 2005-06-21 2006-04-17 Composés herbicides de type benzoxazine n-substituée par un groupe carboxyle

Country Status (3)

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JP (1) JP4838306B2 (fr)
CN (1) CN100387582C (fr)
WO (1) WO2006136073A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116082325A (zh) * 2022-12-25 2023-05-09 浙江工业大学 含异噁唑杂环的苯并噁嗪酮类化合物及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103755658B (zh) * 2014-01-28 2016-06-01 迈克斯(如东)化工有限公司 苯并内酰胺化合物及其合成方法和应用
CN114751871B (zh) * 2022-04-06 2023-08-04 南京农业大学 含α-羟基羧酸片段的噁嗪类化合物的合成及其应用和农药除草剂

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
JPS62277383A (ja) * 1986-01-13 1987-12-02 Sumitomo Chem Co Ltd Ｎ―（ベンズオキサジニル）テトラヒドロフタルイミド誘導体およびそれを有効成分とする除草剤
US4798620A (en) * 1986-09-06 1989-01-17 Nihon Tokushu Noyaku Seizo K.K. Benzoxazines and herbicidal use
JP2001328911A (ja) * 2000-05-17 2001-11-27 Mitsubishi Chemicals Corp 除草剤組成物
CN1442416A (zh) * 2003-03-31 2003-09-17 湖南化工研究院 一种具有生物活性的杂环取代苯并噁嗪环类化合物

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US4789620A (en) * 1986-03-03 1988-12-06 Mitsubishi Rayon Co. Ltd. Liquid photosensitive resin composition containing carboxylated epoxy acrylates or methacrylates
JPS63277675A (ja) * 1987-05-09 1988-11-15 Nippon Tokushu Noyaku Seizo Kk 新規ベンゾオキサジン類
JPH01197481A (ja) * 1988-02-02 1989-08-09 Nippon Tokushu Noyaku Seizo Kk 新規ベンゾオキサジン類及び除草剤としての利用
JPS6434982A (en) * 1987-07-30 1989-02-06 Nissan Chemical Ind Ltd Condensed heterocyclic derivative, production thereof and herbicide containing said derivative as active ingredient
JPH02288878A (ja) * 1988-04-20 1990-11-28 Sumitomo Chem Co Ltd イミド化合物、その製造法、その用途、その中間体、中間体の製造法および中間体の用途
JPH02164802A (ja) * 1988-12-19 1990-06-25 Nippon Tokushu Noyaku Seizo Kk 畑地用除草剤
DE3936826A1 (de) * 1989-11-04 1991-05-08 Bayer Ag N-aryl-stickstoffheterocyclen

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
JPS62277383A (ja) * 1986-01-13 1987-12-02 Sumitomo Chem Co Ltd Ｎ―（ベンズオキサジニル）テトラヒドロフタルイミド誘導体およびそれを有効成分とする除草剤
US4798620A (en) * 1986-09-06 1989-01-17 Nihon Tokushu Noyaku Seizo K.K. Benzoxazines and herbicidal use
JP2001328911A (ja) * 2000-05-17 2001-11-27 Mitsubishi Chemicals Corp 除草剤組成物
CN1442416A (zh) * 2003-03-31 2003-09-17 湖南化工研究院 一种具有生物活性的杂环取代苯并噁嗪环类化合物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116082325A (zh) * 2022-12-25 2023-05-09 浙江工业大学 含异噁唑杂环的苯并噁嗪酮类化合物及其制备方法和应用
CN116082325B (zh) * 2022-12-25 2024-04-16 浙江工业大学 含异噁唑杂环的苯并噁嗪酮类化合物及其制备方法和应用

Also Published As

Publication number Publication date
JP4838306B2 (ja) 2011-12-14
CN1884267A (zh) 2006-12-27
JP2008546722A (ja) 2008-12-25
CN100387582C (zh) 2008-05-14

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