CN100387582C - N-carboxylic acid derivative substituted benzooxazine compounds with herbicidal activity - Google Patents
N-carboxylic acid derivative substituted benzooxazine compounds with herbicidal activity Download PDFInfo
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- CN100387582C CN100387582C CNB2005100317243A CN200510031724A CN100387582C CN 100387582 C CN100387582 C CN 100387582C CN B2005100317243 A CNB2005100317243 A CN B2005100317243A CN 200510031724 A CN200510031724 A CN 200510031724A CN 100387582 C CN100387582 C CN 100387582C
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- oxygen
- fluoro
- dihydrobenzo
- oxazine
- isoindole
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pest Control & Pesticides (AREA)
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- Agronomy & Crop Science (AREA)
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- Wood Science & Technology (AREA)
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- 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
The present invention relates to a benzoxazine compound substituted by N-carboxyl acid derivative, which is shown by the general formula (I). The compound of the present invention has good weeding activity, the preventing effect on most broad-leaved weed is equal to or bigger than 90% in 15 gai/ha dosage for soil processing before seedling planting or 7.5 gai/ha dosage for stem and leaf processing after seedling planting, and the present invention has certain preventing effect on partial single-cotyledon weed and is safe to one or more kinds of crops, such as corn, wheat, peanut, etc.
Description
Technical field:
The present invention relates to benzo oxazinyl compound that a kind of N-carboxylic acid derivative with weeding activity replaces, its preparation method and as the purposes of weedicide.
Background technology:
According to the literature 1,2,4,5-four substituted benzenes and fused heterocycle four substituted benzene compounds are a kind of proporphyrinogen oxidase inhibitors, have efficient weeding activity, and many patents reports are arranged external the sixth of the twelve Earthly Branches.For example: EP420194, USP4640707, USP5084084, USP5127935, USP5322835, USP6323154, DE3922107, JP03,47180, USP5232898, JP62277383, EP362615 etc. have reported a lot of fused heterocycle four substituted benzene compounds and compound preparation has weeding activity.Wherein, the substituent variation of N-on the benzoxazine ring has great influence to biological activity, selectivity and the crop safety of compound.Do not see at present the report of the benzoxazine lopps compound that the replacement of N-carboxylic acid derivative is arranged.
Summary of the invention: the benzo oxazinyl compound that the object of the present invention is to provide N-carboxylic acid derivative replacement with weeding activity.The chemical structure of this compounds is represented with general structure (I):
In the general formula (I):
Het is
X is a hydrogen, halogen, and cyano group, methyl, optimum is a fluorine;
Y is an oxygen, NH, and optimum is an oxygen;
R
1Be hydrogen, halogen, methyl, phenyl, optimum is hydrogen or methyl;
R
2Be (C
1-C
4) alkyl, (C
1-C
4) alkoxyalkyl, optimum is methyl or ethyl;
R
3, R
4Be identical or different hydrogen, (C
1-C
8) alkyl, phenyl, halogenophenyl, R when optimum
3Be hydrogen or methyl, R
4Be methyl or phenyl;
R
mBe a replacement or polysubstituted, an identical or different hydrogen, (C
1-C
4) alkyl, nitro, halogens such as fluorine, chlorine, bromine, iodine, wherein m represents substituent number, optional 1,2,3 or 4, optimum R
mBe hydrogen or fluorine.
Preparation method of the present invention is as follows:
When Het is (II) in the formula of of the present invention (I), compd E
1With F
1The preparation method be:
When Het is (III) in the formula of of the present invention (I), compd E
2With F
2The preparation method be:
Intermediate (A) but method that reference US4734124 describes is synthetic.
Intermediate (A) adds corresponding (hydrogenation) phthalic anhydride (B that replaces in appropriate solvent
1Or B
2), being heated to 30～150 ℃, stirring reaction obtained C in 1～12 hour
1Or C
2Wherein solvent is a glacial acetic acid preferably; Mol ratio is A: B preferably
1Or B
2=1: 1.2; Preferable temperature of reaction is selected solvent refluxing temperature; The more excellent reaction times is 3 hours.
Compound (C
1Or C
2) adding acid binding agent and halogenated carboxylic ester (D in appropriate solvent
1Or D
2) stoichiometric number hour obtains ester class target compound (E
1Or E
2), wherein solvent is DMF preferably, and acid binding agent is a salt of wormwood preferably, and material proportion is (C preferably
1Or C
2): halogenide: salt of wormwood=1: 1: 1.2 (mol ratio), preferable temperature of reaction are about 25 ℃, and the more excellent reaction times is 8 hours.
Ester class target compound (E
1Or E
2) in appropriate solvent, obtain amides target compound (F with the amine reaction
1Or F
2), wherein solvent is methyl alcohol and ethanol preferably, material proportion is (E preferably
1Or E
2): amine=1: 1.3 (mol ratio), about 25 ℃ of preferable temperature of reaction, the more excellent reaction times is 4 hours.
The invention provides the compound and the physico-chemical property of part general formula (I), see Table 1.
Measure through biological screening, the compound of general formula of the present invention (I) has extraordinary weeding activity, the part of compounds weeding activity is better than the conventional weedicide of use at present, when cauline leaf is handled behind the seedling under the dosage of soil treatment or 7.5ga.i/ha before the seedling under the dosage of 15ga.i/ha, weeds preventive effect 〉=90% to most of broad-leaved, the part monocotyledon weed also there is certain preventive effect, to one or more crop safeties such as corn, wheat, peanuts.
Embodiment:
The preparation of embodiment 1:2-(7-fluoro-6-(5-methyl isophthalic acid, 3-dioxy isoindole-2-yl)-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl propionate (compd E 1-08 in the table 1).
Get the amino benzoxazinone 1.82g of 7-fluoro-6-, be dissolved in the 20mL glacial acetic acid, add 1.99g 5-methylphthalic acid acid anhydride, reflux is 4 hours then.Cooling is poured in the 200mL frozen water, filters out solid, washing, and drying, precipitation gets intermediate.
Add 2.07g Anhydrous potassium carbonate, 30mL DMF, above-mentioned intermediate in the there-necked flask, slowly drip 2.17g 2 bromopropionic acid ethyl ester under the stirring at room half little room temperature then, dropwise, room temperature reaction 5 hours is in the impouring frozen water, use ethyl acetate extraction, washing, drying, the silica gel column chromatography separation obtains target compound (E1-08) 2.32g, purity 94%, yield are 52.5%.m.p.179.0-181.1℃。
1H?NMR(CDCl
3，ppm)δ-1.56-1.63(m，3H，
OCH 2 CH 3 )，2.56(s，3H，
Ph-CH 3 )，4.21-4.24(m，2H，
OCH 2 CH
3)，4.64(s，2H，
OCH 2 )，4.72(s，2H，
NCH 2 )，5.35-5.37(m，1H，CH)，6.65(d，J＝6.6Hz，1H，Ph-H)，6.92(d，J＝9.9Hz，1H，Ph-H)，7.59-7.86(m，3H，Ar-H)。
Embodiment 2:2-(the preparation of 6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl acetate (compd E 2-04 in the table 1).
Get the amino benzoxazinone 1.82g of 7-fluoro-6-, be dissolved in the 20mL glacial acetic acid, add 1.67g 3,4,5, the 6-tetrahydrophthalic anhydride, reflux is 4 hours then.Cooling is poured in the 200mL frozen water, filters out solid, washing, and drying, precipitation gets intermediate.
Table 1: the chemical structure and the fusing point of the The compounds of this invention of part shown in general formula (I)
Add the 2.07g Anhydrous potassium carbonate in the there-necked flask, 30mL DMF and above-mentioned intermediate, stirring at room half an hour, slowly drip the 2.0g ethyl bromoacetate then under the room temperature, dropwise, room temperature reaction 6 hours is in the impouring frozen water, use ethyl acetate extraction, washing, drying, the silica gel column chromatography separation obtains target compound (E2-04) 1.70g, purity 96%, yield are 40.8%.m.p.116.0-118.3℃。
1H?NMR(CDCl
3，ppm)δ：1.26(t，J＝6.6Hz，3H，
OCH 2 CH 3 )，1.82-1.85(m，4H，2×
CH 2 )，2.41-2.45(m，4H，2×
CH 2 )，4.22-4.25(m，2H，
OCH 2 CH
3)，4.61(s，2H，
OCH 2 )，4.71(s，2H，
NCH 2 )，6.61(d，J＝6.6Hz，1H，Ar-H)，6.91(d，J＝9.6Hz，1H，Ar-H)。
Embodiment 3:2-(the preparation of 6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) N-methylacetamide (compound F 17-hydroxy-corticosterone 2-01 in the table 1).
Add in the there-necked flask 2-(6-(and 1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl acetate (E2-04) 2.01g, 30mL dehydrated alcohol, the ethanolic soln of Dropwise 5 mL (27～32%) methylamine slowly under the stirring at room, dropwise, room temperature reaction 8 hours is separated out precipitation, filter washing, drying, the silica gel column chromatography separation obtains target compound (F2-01) 1.61g, purity 97%, and yield is 80.8%.m.p.253.0-254.6℃。
1H?NMR(CDCl
3，ppm)δ：2.80(d，J＝4.8Hz，3H，
NHCH 3 )，1.81-1.83(m，4H，2×
CH 2 >)，2.41-2.43(m，4H，2×
CH 2 )，4.46(s，2H，
OCH 2 )，4.72(s，2H，
NCH 2 )，6.17(s，1H，
NHCH 3 )，6.89(d，J＝9.9Hz，1H，Ar-H)，7.09(d，J＝6.9Hz，1H，Ar-H)。
Application Example 1: potted plant weeding test
Accurately take by weighing sample, after the The suitable solvent dissolving, add small amounts of emulsifiers, adding distil water is settled to 10ml and adopts suitable spraying machine sprinkling again, and reduced unit's area dose is 7.5gai/ha and 15gai/ha.At sectional area 64cm
2The plastic tub alms bowl in quantitative dress soil, flatten, water permeable, choose full seed, dicotyledonous select for use lamb's-quarters (Chenopodium album), piemarker (Abutilon theophrasti), recessed amaranth (Amaranthusascedense) of the same size, unifacial leaf is selected lady's-grass (Digitaria sanguinalis), barnyard grass grass (Echinochloacrus-galli), Herba Setariae Viridis (Setaria viridis) for use, divide single, double cotyledon plant to divide the pot culture kind, respectively account for 1/3 of alms bowl area, cover thick fine earth of 1cm and trickle, place hot-house culture.Treat that unifacial leaf examination material grows to 1 heart stage of 1 leaf, dicotyledonous examination material grows to 2 leaf periods, carry out seedling with soup after the cauline leaf spraying handle, soil treatment before the seedling is carried out in the sowing of examination material next day.Put back to the greenhouse subsequently.Range estimation overground part growing state after 15 days calculates growth inhibition ratio according to following formula: growth inhibition ratio (%)=100* (contrast plant height-processing plant height)/contrast plant height.
Table 2 has been listed part of compounds of the present invention, as the inhibition effect to cauline leaf processing behind soil treatment and the bud before the potted plant examination material plant bud such as E2-01, E2-02, E2-04, E2-05, E2-08.As shown in table 2,5 compounds of test are under the low dosage of 7.5g ai/ha and 15.0g ai/ha, and cauline leaf is handled broadleaf weeds is had preventive effect preferably behind preceding soil treatment of bud or the bud, and the part monocotyledon weed is also had certain preventive effect.
Table 2: potted plant weeding test-results
Application Example 2: crop safety test.
Choose full seed, paddy rice Oryza sativa of the same size, wheat Triticum aestivum, corn Zea mays, Chinese sorghum sorghum vulgare, soybean Glycine max, rape Brassicacampestris, cotton Gossypium spp and peanut seed, use 0.1%HgCl
2Sterilization 5min, the back leaches and puts into little porcelain dish (putting wetting thieving paper) at 25 ℃ of growth chamber vernalization 24h with the distilled water 12h that soaks seed, and gets 10 in the consistent seed of size and bud length, is sowed at 64cm
2Quantitatively in the plastic tub alms bowl of dress soil, cover thick fine earth of 1cm and trickle, place hot-house culture.Treat that unifacial leaf examination material grows to 1 heart stage of 1 leaf, dicotyledonous examination material grows to 2 leaf periods, with 150,120,75,, 30,15,7.5,1.5g ai/ha soup carry out seedling after the cauline leaf spraying handle, the examination material is sowed and is carried out the preceding soil treatment of seedling next day, be contrast with spraying solvent and clear water respectively, twice repetition, handle the examination material and place hot-house culture, observe the crop symptom of being injured after 15 days, range estimation overground part growth inhibition ratio.Growth inhibition ratio (%)=100 (contrast plant height-processing plant height)/contrast plant height is according to growth inhibition ratio estimation crop IC '
10Value, and in conjunction with weeds IC
90Value is pressed IC '
10/ IC
90Calculate selectivity index (Z), safety grades standard: A:Z 〉=4; B:2≤Z＜4; C:1≤Z＜2, D:Z＜1 can be considered safety more than the B level.Compound of the present invention such as E2-05, E2-08 etc. the results are shown in Table 3 to the safety experiment of crop.
As table 3 as seen: soil treatment is to paddy rice, wheat, corn, cotton, Soybean and Other Crops safety under the dosage of 15g ai/ha for compd E 2-05, and cauline leaf is handled wheat, corn safety under the dosage of 7.5g ai/ha.Soil treatment is to wheat, peanut and other crops safety under the dosage of 37.5g ai/ha for compd E 2-08, and cauline leaf is handled wheat safety under the dosage of 15g ai/ha.
Table 3: crop safety experimental result
Annotate :/expression is test not.
Claims (3)
1.N-the benzo oxazinyl compound that carboxylic acid derivative replaces, it is characterized in that the having general formula structure of (I):
Wherein
Het is
X is a hydrogen, halogen, cyano group, methyl;
Y is an oxygen, NH;
R
1Be hydrogen, halogen, methyl, phenyl;
R
2Be (C
1-C
4) alkyl, (C
1-C
4) alkoxyalkyl;
R
3, R
4Be identical or different hydrogen, (C
1-C
8) alkyl, phenyl, halogenophenyl;
R
mBe identical or different hydrogen, (C
1-C
4) alkyl, nitro, halogenic substituent, wherein m represents substituent number, optional 1,2,3 or 4.
2. the benzo oxazinyl compound that N-carboxylic acid derivative according to claim 1 replaces, its characterization compound is:
2-(7-fluoro-6-(5-methyl isophthalic acid, 3-dioxy isoindole-2-yl)-3-oxygen-2, and 3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl propionate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) methyl acetate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) methyl propionate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl acetate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) ethyl propionate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) phenylacetic acid ethyl ester
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-2-methyl-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) methyl acetate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-2-methyl-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl) methyl propionate
2-(6-(1,3-dioxy-4,5,6,7-tetrahydrochysene-1H-isoindole-2 (3H)-yl)-7-fluoro-3-oxygen-2,3-dihydrobenzo [b] [1,4] oxazine-4-yl)-N-methylacetamide.
3. the purposes of the benzo oxazinyl compound that N-carboxylic acid derivative according to claim 1 and 2 replaces is characterized in that: broad-leaved, monocotyledon weed are had weeding activity, and to corn, wheat, Peanut Crop safety.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100317243A CN100387582C (en) | 2005-06-21 | 2005-06-21 | N-carboxylic acid derivative substituted benzooxazine compounds with herbicidal activity |
| JP2008517296A JP4838306B2 (en) | 2005-06-21 | 2006-04-17 | N-carboxylic acid derivative-substituted benzoxazines having herbicidal activity |
| PCT/CN2006/000691 WO2006136073A1 (en) | 2005-06-21 | 2006-04-17 | Herbicidal n-carboxyl substituted benzoxazine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100317243A CN100387582C (en) | 2005-06-21 | 2005-06-21 | N-carboxylic acid derivative substituted benzooxazine compounds with herbicidal activity |
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| Publication Number | Publication Date |
|---|---|
| CN1884267A CN1884267A (en) | 2006-12-27 |
| CN100387582C true CN100387582C (en) | 2008-05-14 |
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ID=37570091
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100317243A Active CN100387582C (en) | 2005-06-21 | 2005-06-21 | N-carboxylic acid derivative substituted benzooxazine compounds with herbicidal activity |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4838306B2 (en) |
| CN (1) | CN100387582C (en) |
| WO (1) | WO2006136073A1 (en) |
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| CN103755658B (en) * | 2014-01-28 | 2016-06-01 | 迈克斯(如东)化工有限公司 | Benzolactam compounds and synthetic method thereof and application |
| CN114751871B (en) * | 2022-04-06 | 2023-08-04 | 南京农业大学 | Synthesis and application of oxazine compound containing alpha-hydroxycarboxylic acid fragment and pesticide herbicide |
| CN116082325B (en) * | 2022-12-25 | 2024-04-16 | 浙江工业大学 | Benzoxazinone compound containing isoxazole heterocycle, and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4789620A (en) * | 1986-03-03 | 1988-12-06 | Mitsubishi Rayon Co. Ltd. | Liquid photosensitive resin composition containing carboxylated epoxy acrylates or methacrylates |
| JPH02164802A (en) * | 1988-12-19 | 1990-06-25 | Nippon Tokushu Noyaku Seizo Kk | Herbicide for upland field |
| CN1442416A (en) * | 2003-03-31 | 2003-09-17 | 湖南化工研究院 | Helerocyclic substituted benzoxazine cyclic compound having biological activity |
Family Cites Families (9)
| 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 |
| JPH0676406B2 (en) * | 1986-01-13 | 1994-09-28 | 住友化学工業株式会社 | N- (Benzoxazinyl) tetrahydrophthalimide derivative and herbicide containing it as an active ingredient |
| JPS63277675A (en) * | 1987-05-09 | 1988-11-15 | Nippon Tokushu Noyaku Seizo Kk | Novel benzoxazines |
| JPH01197481A (en) * | 1988-02-02 | 1989-08-09 | Nippon Tokushu Noyaku Seizo Kk | Novel benzoxazines and utilization thereof as herbicide |
| EP0290863A3 (en) * | 1987-05-09 | 1989-03-15 | Nihon Tokushu Noyaku Seizo K.K. | Benzoxazine derivative, process and intermediates for its preparation and its use as herbicide |
| 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 (en) * | 1988-04-20 | 1990-11-28 | Sumitomo Chem Co Ltd | Imide compound, production, use and intermediate thereof, production of same intermediate and use of same intermediate |
| DE3936826A1 (en) * | 1989-11-04 | 1991-05-08 | Bayer Ag | N-ARYL NITROGEN HETEROCYCLES |
| JP2001328911A (en) * | 2000-05-17 | 2001-11-27 | Mitsubishi Chemicals Corp | Herbicidal composition |
-
2005
- 2005-06-21 CN CNB2005100317243A patent/CN100387582C/en active Active
-
2006
- 2006-04-17 WO PCT/CN2006/000691 patent/WO2006136073A1/en active Application Filing
- 2006-04-17 JP JP2008517296A patent/JP4838306B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4789620A (en) * | 1986-03-03 | 1988-12-06 | Mitsubishi Rayon Co. Ltd. | Liquid photosensitive resin composition containing carboxylated epoxy acrylates or methacrylates |
| JPH02164802A (en) * | 1988-12-19 | 1990-06-25 | Nippon Tokushu Noyaku Seizo Kk | Herbicide for upland field |
| CN1442416A (en) * | 2003-03-31 | 2003-09-17 | 湖南化工研究院 | Helerocyclic substituted benzoxazine cyclic compound having biological activity |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4838306B2 (en) | 2011-12-14 |
| CN1884267A (en) | 2006-12-27 |
| JP2008546722A (en) | 2008-12-25 |
| WO2006136073A1 (en) | 2006-12-28 |
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