CN102250078A - Use of 4-(benzofuran-5-yl)-2-benzyliminothiazole in preparation of herbicide - Google Patents
Use of 4-(benzofuran-5-yl)-2-benzyliminothiazole in preparation of herbicide Download PDFInfo
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- CN102250078A CN102250078A CN2011101024438A CN201110102443A CN102250078A CN 102250078 A CN102250078 A CN 102250078A CN 2011101024438 A CN2011101024438 A CN 2011101024438A CN 201110102443 A CN201110102443 A CN 201110102443A CN 102250078 A CN102250078 A CN 102250078A
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- 0 CC(C)(C1)Oc(c(O*)c2)c1cc2C(N1)=C(*)S[C@]1N=Cc1ccccc1 Chemical compound CC(C)(C1)Oc(c(O*)c2)c1cc2C(N1)=C(*)S[C@]1N=Cc1ccccc1 0.000 description 2
- PPNXPRRUKVQFEB-PGGKNCGUSA-N CC(C)(C1)Oc(c(OC)c2)c1cc2-c1c[s]c(/N=C/c(cc(cc2I)I)c2O)n1 Chemical compound CC(C)(C1)Oc(c(OC)c2)c1cc2-c1c[s]c(/N=C/c(cc(cc2I)I)c2O)n1 PPNXPRRUKVQFEB-PGGKNCGUSA-N 0.000 description 1
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Abstract
The invention discloses the use of 4-(benzofuran-5-yl)-2-benzyliminothiazole shown by a chemical structural formula I in the preparation of herbicide. In the formula, X may be chlorine, fluorine, hydroxy, methoxyl, ethyoxyl, nitro, dimethylamino, sulfo, methylsulfonylamino, sufamyl, 2-chloro-5-nitro, 3-ethyl-4-hydroxy, 3,4-dimethoxy, 2,4-dichloro, 2-hydroxy-5-bromo, 2-hydroxy-5- iodo, 2-hydroxy-5-chloro, 2,4,-dichloro, 2-hydroxy-3,5-dichloro, 2-hydroxy-3,5-dichloro, 2-hydroxy-3,5-dibromo or 2-hydroxy-3,5-diiodo; R may be H, C1 to C2 alkyl, C3 to C4 straight-chain alkyl or branched-chain alkyl; and R1 may be H, C1 to C2 alkyl and C3 to C4 straight-chain alkyl or branched-chain alkyl.
Description
Technical field
The present invention relates to the new purposes of a compounds, it specifically is 4-(cumarone-5-yl)-2-benzyl imino-thiazole, be 4-(7-hydroxyl/alkoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-benzyl imino-thiazole and conduct preparation herbicide applications thereof.
Background technology
Chinese patent (CN102010405) has been described 4-(cumarone-5-yl)-2-benzyl imino-thiazole and preparation method thereof and its application as antitumor drug.
Summary of the invention
The object of the present invention is to provide the 4-shown in the chemical structural formula I (cumarone-5-yl)-2-benzyl imino-thiazole as the preparation herbicide applications.4-(cumarone-5-yl)-2-benzyl imino-thiazole chemistry 4-(7-hydroxyl/alkoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl) by name-2-benzyl imino-thiazole.
Wherein, X is selected from: 2-chlorine, the 2-fluorine, the 2-hydroxyl, the 2-methoxyl group, the 2-oxyethyl group, the 2-nitro, the 3-dimethylamino, 3-chlorine, the 3-bromine, the 3-fluorine, the 3-methyl, the 3-ethyl, the 3-trifluoromethyl, the 3-hydroxyl, the 3-methoxyl group, the 3-oxyethyl group, the 3-nitro, the 3-sulfonic group, the 3-methanesulfonamido, the 3-sulfamyl, the 4-dimethylamino, 4-chlorine, the 4-bromine, the 4-fluorine, the 4-methyl, the 4-ethyl, the 4-trifluoromethyl, the 4-hydroxyl, the 4-methoxyl group, the 4-oxyethyl group, the 4-acetoxyl group, the 4-nitro, the 4-sulfonic group, the 4-methanesulfonamido, the 4-sulfamyl, 2-chloro-5-nitro, 3-ethyl-4-hydroxyl, 3, the 4-dimethoxy, 2, the 4-dichloro, 2-hydroxyl-5-bromine, 2-hydroxyl-5-iodine, 2-hydroxyl-5-chlorine, 2, the 4-difluoro, 2-hydroxyl-3, the 5-difluoro, 2-hydroxyl-3, the 5-dichloro, 2-hydroxyl-3,5-dibromo or 2-hydroxyl-3, the 5-diiodo-; R is selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl; R
1Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl.
The objective of the invention is to also provide 4-(cumarone-5-yl)-2-benzyl imino-thiazole is 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(2-hydroxyl-3,5-diiodo-benzyl imino-) thiazole removes the herbicide applications of thorn amaranth or lamb's-quarters as preparation.
The present invention compared with prior art has following advantage:
4-(cumarone-5-yl)-2-benzyl imino-thiazole (I) has weeding activity, can be used for preparing weedicide.
Embodiment
Following examples are intended to illustrate the present invention rather than limitation of the invention further.
The weeding activity of embodiment 1 4-(cumarone-5-yl)-2-benzyl imino-thiazole is measured
1 test objective
In indoor general sieve new compound virulence to piemarker, thorn amaranth, lamb's-quarters, lady's-grass and dog tail under confession examination concentration, estimate its weeding activity.
2 test conditionss
2.1 for the examination target
Target is piemarker (Abutilon theophrasti), thorn amaranth (Amaranthus spinosus L), lamb's-quarters (Chenopodiumalbum), lady's-grass (Digitaria sanguinalis), barnyard grass (Echinochloa crus-galli) and dog tail (Setaria viridis).
2.2 culture condition
Culture condition for examination target and test back target is 20 ± 5 ℃ of temperature, relative humidity 65 ± 5%.
2.3 plant and instrument
Electronic balance (sensibility reciprocal ten thousand/), 100ml beaker, graduated cylinder, crop spraying machine etc.
3 test design
3.1 test medicine 4-(cumarone-5-yl)-2-benzyl imino-thiazole.
3.2 the general sieve of experimental concentration is established single dose 2250g ai/ha.
3.3 medicament preparation
Take by weighing 4-(cumarone-5-yl)-2-benzyl imino-thiazole aequum with ten thousand/electronic balance; Solvent: N, dinethylformamide (DMF), 0.2%; Emulsifying agent: Tween80,0.1%; Add clear water and be diluted to desired concn.
4 test methods
With reference to " pesticide bioactivity is estimated SOP ".Cauline leaf is handled treatment dosage 2250g ai/ha after adopting NY/T 1155.4-2000 standard to carry out seedling.At sectional area 64cm
2The plastic tub alms bowl in quantitatively the dress soil pressure is flat, place Stainless steel basin, choose full seed, seed of the same size, divide single, double cotyledon plant to divide the alms bowl sowing, respectively account for 1/3 of alms bowl area, cover the thick fine earth of 1cm, add water to upper layer of soil from plastic tub alms bowl bottom and soak into, place hot-house culture, treat unifacial leaf examination material grow to 1 heart stage of 1 leaf, dicotyledonous examination material grow to 2 leaf periods and carry out seedling after cauline leaf handle; Observe target after 15 days and germinate and growing state, the range estimation growth inhibition ratio.Clear water contrast and solvent control are established in test, and every processing repeats for 3 times.
5 investigation methods and evaluated biological activity method
Observe target after 15 days and germinate and growing state, the range estimation growth inhibition ratio.
6 general sieve results
By the general sieve of weeding activity to 4-(cumarone-5-yl)-2-benzyl imino-thiazole.Carry out cauline leaf and handle under 2250g ai/ha concentration, wherein 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(2-hydroxyl-3,5-diiodo-benzyl imino-) thiazole is 50% to the weeding activity of thorn amaranth and lamb's-quarters.
4-(cumarone-5-yl)-2-benzyl imino-thiazole has weeding activity preferably, can be used as the preparation herbicide applications.
Claims (2)
1. the 4-shown in the chemical structural formula I (cumarone-5-yl)-2-benzyl imino-thiazole is as preparing herbicide applications:
Wherein, 4-(cumarone-5-yl)-2-benzyl imino-thiazole chemistry 4-(7-hydroxyl/alkoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl) by name-2-benzyl imino-thiazole; X is selected from: 2-chlorine, the 2-fluorine, the 2-hydroxyl, the 2-methoxyl group, the 2-oxyethyl group, the 2-nitro, the 3-dimethylamino, 3-chlorine, the 3-bromine, the 3-fluorine, the 3-methyl, the 3-ethyl, the 3-trifluoromethyl, the 3-hydroxyl, the 3-methoxyl group, the 3-oxyethyl group, the 3-nitro, the 3-sulfonic group, the 3-methanesulfonamido, the 3-sulfamyl, the 4-dimethylamino, 4-chlorine, the 4-bromine, the 4-fluorine, the 4-methyl, the 4-ethyl, the 4-trifluoromethyl, the 4-hydroxyl, the 4-methoxyl group, the 4-oxyethyl group, the 4-acetoxyl group, the 4-nitro, the 4-sulfonic group, the 4-methanesulfonamido, the 4-sulfamyl, 2-chloro-5-nitro, 3-ethyl-4-hydroxyl, 3, the 4-dimethoxy, 2, the 4-dichloro, 2-hydroxyl-5-bromine, 2-hydroxyl-5-iodine, 2-hydroxyl-5-chlorine, 2, the 4-difluoro, 2-hydroxyl-3, the 5-difluoro, 2-hydroxyl-3, the 5-dichloro, 2-hydroxyl-3,5-dibromo or 2-hydroxyl-3, the 5-diiodo-; R is selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl; R
1Be selected from: H, C
1～C
2Alkyl, C
3～C
4Straight chained alkyl or branched-chain alkyl.
2. the described 4-of claim 1 (cumarone-5-yl)-2-benzyl imino-thiazole is a 4-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(2-hydroxyl-3,5-diiodo-benzyl imino-) thiazole removes the herbicide applications of thorn amaranth or lamb's-quarters as preparation:
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| CN 201110102443 CN102250078B (en) | 2011-04-25 | 2011-04-25 | Use of 4-(benzofuran-5-yl)-2-benzyliminothiazole in preparation of herbicide |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603726A (en) * | 2012-01-18 | 2012-07-25 | 湖南化工研究院 | 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method |
| CN104774199A (en) * | 2014-01-09 | 2015-07-15 | 湖南大学 | 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole, and preparation and applications thereof |
| CN105985332A (en) * | 2015-02-10 | 2016-10-05 | 湖南大学 | 2-[5-(triazolyl-1-yl)thiazolyl-2-imino]-5-benzalthiazolinone and its preparation method and use |
| CN106083780A (en) * | 2016-06-08 | 2016-11-09 | 河北大学 | N (2,3 Dihydrobenzofuranes 7 epoxide) alkanol and its preparation method and application |
| CN110016019A (en) * | 2019-04-30 | 2019-07-16 | 河北大学 | A kind of furodiazole derivative and the preparation method and application thereof based on benzofuranol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101781269A (en) * | 2010-02-08 | 2010-07-21 | 湖南大学 | 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof |
| CN102010405A (en) * | 2010-11-08 | 2011-04-13 | 湖南大学 | 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent |
-
2011
- 2011-04-25 CN CN 201110102443 patent/CN102250078B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101781269A (en) * | 2010-02-08 | 2010-07-21 | 湖南大学 | 4-tertiary butyl-2-(nitrobenzyl imino) thiazole derivative as well as preparation method and application thereof |
| CN102010405A (en) * | 2010-11-08 | 2011-04-13 | 湖南大学 | 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603726A (en) * | 2012-01-18 | 2012-07-25 | 湖南化工研究院 | 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method |
| CN102603726B (en) * | 2012-01-18 | 2014-08-13 | 湖南化工研究院 | 5-(2-aminothiazole-4-yl) benzofuranol etheric compound with herbicidal activity and preparation method |
| CN104774199A (en) * | 2014-01-09 | 2015-07-15 | 湖南大学 | 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole, and preparation and applications thereof |
| CN104774199B (en) * | 2014-01-09 | 2017-03-08 | 湖南大学 | 2‑（2 benzyl hydrazono-s）‑5‑（1,2,4 triazole, 1 base）Thiazole and its preparation and application |
| CN105985332A (en) * | 2015-02-10 | 2016-10-05 | 湖南大学 | 2-[5-(triazolyl-1-yl)thiazolyl-2-imino]-5-benzalthiazolinone and its preparation method and use |
| CN105985332B (en) * | 2015-02-10 | 2018-09-21 | 湖南大学 | 2- [5- (nitrogen azoles -1- bases) thiazole -2- imino groups] -5- benzal thiazolinones and the preparation method and application thereof |
| CN106083780A (en) * | 2016-06-08 | 2016-11-09 | 河北大学 | N (2,3 Dihydrobenzofuranes 7 epoxide) alkanol and its preparation method and application |
| CN106083780B (en) * | 2016-06-08 | 2018-05-08 | 河北大学 | N- (2,3- Dihydrobenzofuranes -7- epoxides) alkanol and its preparation method and application |
| CN110016019A (en) * | 2019-04-30 | 2019-07-16 | 河北大学 | A kind of furodiazole derivative and the preparation method and application thereof based on benzofuranol |
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| CN102250078B (en) | 2013-06-05 |
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Application publication date: 20111123 Assignee: HUBEI XIANGHE PRECISION CHEMICAL CO., LTD. Assignor: Hunan University Contract record no.: 2014420000056 Denomination of invention: Application of 4- (benzo -5- group) -2- benzyl thiazole as preparation of herbicide Granted publication date: 20130605 License type: Exclusive License Record date: 20140429 |
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