CN101007799A - Pyrimidine salicylic acid cluster molecule with herbicide activity - Google Patents

Pyrimidine salicylic acid cluster molecule with herbicide activity Download PDF

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CN101007799A
CN101007799A CN 200710003030 CN200710003030A CN101007799A CN 101007799 A CN101007799 A CN 101007799A CN 200710003030 CN200710003030 CN 200710003030 CN 200710003030 A CN200710003030 A CN 200710003030A CN 101007799 A CN101007799 A CN 101007799A
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宁君
梅向东
赵前飞
衣悦涛
马洪菊
杨国权
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Institute of Plant Protection of CAAS
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Abstract

分子式为式Ⅰ，的化合物，其中各基团按说明书中所定义。

Figure 200710003030

The molecular formula is the compound of formula I, wherein each group is as defined in the description.

Figure 200710003030

Description

Pyrimidine salicylic acid cluster molecule with weeding activity
Technical field
The invention belongs to agricultural herbicide.
Background technology
In recent years, scientist finds in the research of active oligosaccharides, if after the active oligosaccharides small molecules of a kind of parent made duster compound, its activity can increase (J.Am.Chem.Soc., 1999,121,8174 sometimes greatly; " carbohydrate chemistry " Kong Fanzuo writes, Science Press 2005).Form duster compound as five identical parent small molecules oligosaccharides, its activity is not to increase by five times, but may increase hundreds and thousands of times.And in recent years, many examples about the duster compound successful Application (J BiolChem, 1994,269 (39): 24349 had appearred in the medical research field; Proc Natl Acad Sci, USA, 1993,90 (19): 9031; JMed Chem, 1999,42 (20): 4225; Angew Chem Int Ed, 1998,37 (20): 2754).
Patent (CN200610078063.4) has proposed the utilization bunch method of closing and has carried out the novel pesticide initiative, relates to the synthetic of duster compounds such as Affirm (Merck Co.) and fluorine worm nitrile.
Summary of the invention
The compound that will have physiologically active generates a small bundle of straw, etc. for silkworms to spin cocoons on compound, and the physiologically active that utilizes cluster effect (cluster effect) (J.Am.Chem.Soc., 1999,121,8174) to improve parent compound has shown very big potentiality in the research of medicine.The cluster effect technology is applied in the research of novel pesticide initiative, utilize this principle that some existing agricultural chemicals or potential pesticide activity molecule are screened, efficient, the low toxicity novel pesticide molecule of development and discovery is to reach the effect of getting twice the result with half the effort.When promoting the cluster effect principle and in the pesticide new variety initiative, use, and expectation obtain activity higher, with the better potential pesticide new variety of Environmental compatibility (Pesticide Science journal .2006,8 (3), 203).
Choose existing its bunch of tool pesticide bioactivity pyrimidine salicylic acid molecule synthesis and close structure.Target organisms with parent compound serves as that the main examination material that supplies suitably enlarges the screening scope.Wish to filter out the duster compound of high several times even tens times of weeding activity than parent pesticide molecule itself, reduce research expenditure and shorten the initiative process, the initiative efficient of raising new variety.
The object of the present invention is to provide a kind of new pyrimidine salicylic acid that just can control various weeds under very little dosage bunch to close molecule, it can be applicable to agricultural and goes up with the control farmland weed.
Technical scheme of the present invention is as follows:
The invention provides a kind of pyrimidine salicylic acid cluster structure, shown in general formula I:
In the formula:
R is H, halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group, (wherein said phenoxy group can be by the halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group for particularly C1-C4 alkyl, or phenoxy group, particularly the C1-C4 alkoxyl group replaces, or lower alkoxy, particularly C1-C4 alkoxyl group replace), or (not) replaces fragrant heterocycle;
A, B, C and D can be identical or different, and each is hydrogen atom naturally, such as the halogen atom of fluorine, chlorine, bromine or iodine, and low alkyl group, particularly C1-C4 alkyl, lower alkoxy, particularly C1-C4 alkoxyl group or halogenated lower alkoxy;
X is O, S, NCHO or CH 2
Y is O or N;
R ' is that (not) replaces C 1-C 18Alkylidene group, (not) replaces C 3-C 8Cycloalkylidene, (not) replaces C 2-C 18Alkenylene, (not) replaces C 3-C 8Inferior cycloalkenyl group, (not) replaces C 2-C 18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C 1-C 18Inferior assorted alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains carbonyl that (not) replaces 1-C 18Alkylidene group, the C that contains amido that (not) replaces 1-C 18Alkylidene group, the C that contains alkylsulfonyl that (not) replaces 1-C 18Alkylidene group, (not) replace contains sulfonic C 1-C 18Alkylidene group etc.;
In the definition of the general formula compound among the present invention (I), compile the following substituting group of used term general proxy:
" alkylidene group " comprises the alkylidene group of straight or branched.Typical alkylidene group has methylene radical, ethylidene, inferior n-propyl, isopropylidene, inferior normal-butyl, inferior sec-butyl, the inferior tertiary butyl, inferior n-pentyl, isopentylidene, inferior n-hexyl, inferior n-heptyl, inferior iso-octyl, nonamethylene, inferior decyl, inferior undecyl, inferior dodecyl and other.
" cycloalkylidene " refers to the compound of fatty family ring structure, as inferior cyclopropane, inferior tetramethylene, inferior pentamethylene, inferior hexanaphthene, inferior suberane, inferior cyclooctane and other.
" alkenylene " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" inferior cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as inferior cyclopentenes, inferior tetrahydrobenzene, 1, and the inferior tetrahydrobenzene of 4-and other.
" alkynylene " refers to undersaturated hydrocarbon group, contains individual or two triple bonds in the straight or branched.
" aryl " refers to monocycle or polynuclear compound, or benzene, naphthalene, indenes, anthracene, dicyclopentadiene and to dihydrobenzene, fluorenes, acenaphthene, phenanthrene and azulene.
" aromatic heterocyclic " refers to monocycle or polycyclic furans, thiophene, pyrroles, piperazine, oxazole, isoxzzole, different thiadiazoles, thiazole, pyrazoles, imidazoles, 1,2,3-triazoles, 1,1,4-triazole, tetrazolium, 1,2, the 3-thiadiazoles, 1,1,4-thiadiazoles, 1,3, the 4-thiadiazoles, 1,1,4-thiadiazoles, 1,3, the 4-thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,1,4-triazine, 1,1,4,5-tetrazine, cumarone, thionaphthene, indoles, the benzisoxa oxazole, benzoxazoles, benzisothiazole, benzothiazole, benzopyrazoles, benzoglyoxaline, benzotriazole, 1,2-methylenedioxyphenyl, ethylene dioxy base benzene, quinoline and isoquinoline 99.9.
In the compound of molecular formula I, be preferably following general formula I-I.
Among the formula I:
R is H, halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group, (wherein said phenoxy group can be by the halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group for particularly C1-C4 alkyl, or phenoxy group, particularly the C1-C4 alkoxyl group replaces, or lower alkoxy, particularly C1-C4 alkoxyl group replace), or (not) replaces fragrant heterocycle;
X is O or S;
R ' is that (not) replaces C 1-C 18Alkylidene group, (not) replaces C 3-C 8Cycloalkylidene, (not) replaces C 2-C 18Alkenylene, (not) replaces C 3-C 8Inferior cycloalkenyl group, (not) replaces C 2-C 18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C 1-C 18Inferior assorted alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains carbonyl that (not) replaces 1-C 18Alkylidene group, the C that contains amido that (not) replaces 1-C 18Alkylidene group, the C that contains alkylsulfonyl that (not) replaces 1-C 18Alkylidene group, (not) replace contains sulfonic C 1-C 18Alkylidene group etc.;
With specific embodiment method of the present invention is further described below, but does not limit the present invention.General formula (I) part of compounds sees Table 1.
Table 1
Figure A20071000303000072
Numbering R R X A B C D
1 6-Cl CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
2 6-Cl CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
3 6-Cl CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
4 6-Cl CH(CH 3)CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
5 6-Cl CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
6 6-Cl CH 2CH(Cl)CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
7 6-Cl CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
8 6-Cl CH 2C(CH 3) 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
9 6-Cl CH 2CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
10 6-Cl CH 2CH 2CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
11 6-Cl CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
12 6-Cl CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
13 6-Cl CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2 S OCH 3 OCH 3 OCH 3 OCH 3
14 6-Cl OCCH 2CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
15 6-Cl OCCH 2CH 2CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
16 6-Cl OCCH(CH 3)CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
17 6-Cl OOCH 2CH 2CH 2CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
18 6-Cl OCCH 2CH(Cl)CH 2CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
19 6-Cl OCCH 2CH 2CH 2CH 2CH 2CO S OCH 3 OCH 3 OCH 3 OCH 3
Figure A20071000303000091
Figure A20071000303000101
Figure A20071000303000111
Figure A20071000303000121
Figure A20071000303000131
Figure A20071000303000141
Figure A20071000303000151
Figure A20071000303000161
Figure A20071000303000171
Figure A20071000303000181
Figure A20071000303000191
Figure A20071000303000201
The expressed compound of general formula (I) is useful as the effective constituent of weedicide.When the compound of general formula of the present invention (I) as weedicide, the formulation that effective constituent is fit to depends on specific purposes and suitable application process.The present invention also comprises by the represented a kind of pyrimidine salicylic acid duster compound and the agriculture formed herbicidal composition of applicable carrier of with weeding activity of general formula (I).
In general, effective constituent is dissolved or dilution with inert solvent and solid carrier.Applied formulation has pulvis, wettable powder, and missible oil, aqua and oil suspending agent, granula, capsules etc. need to add tensio-active agent or other auxiliary agent usually, and fertilizer etc. are used with.
The compounds of this invention can be used as single agent or mixture.In these single agent and mixture, acceptable inert thinner or tensio-active agent such as solid carrier or liquid vehicle are mixed on the agricultural of activeconstituents and routine.Carrier not only can dissolve, disperse effective constituent but also not influence the activity of effective constituent, and itself does not have the obvious damage effect to soil, equipment, crop or agricultural environment.Auxiliary agent is generally tensio-active agent, stablizer, defoamer or dispersion agent in single agent and the mixture.Single agent of the present invention and mixture comprise that also its purpose is to enlarge the field of activity of preparation and improves drug effect with being mixed of known agricultural chemical compound.
Its weight percentage of effective constituent is 0.1% to 99% in the preparation, and contains at least 0.1% to 20% tensio-active agent and 0.1% to 99% solid or liquid diluent.
If the compound of general formula (I) mixes mutually with another weedicide, according to the difference of active compound, application purpose, envrionment conditions and formulation, the content of effective variation range is very big in the mixture.Active constituent content is generally 1% to 95% in the mixture, and suitable content is 5% to 60%.The effective dosage ranges of The compounds of this invention is generally 1 gram/hectare to 3 kg/ha, and 5 gram/hectares are better to 500 gram/hectares.
Other embodiments of the present invention are prevention target crop field (in cotton or rice terrace) method for weed, and this method comprises that the pyrimidine salicylic acid duster compound herbicidal composition that compound shown in the general formula of herbicidally effective amount (I) and acceptable carrier are formed imposes on the surface of growth medium of the places of described weeds, described weeds or described weeds.
Embodiment
With specific embodiment method of the present invention is further described below.
Example 1: the preparation of compound 5
Figure A20071000303000211
At room temperature, 19.6g (60mmol) 2-[(4,6-dimethoxypyridin-2-yl) sulfo-]-6-chloro-benzoic acid and 200ml dimethylbenzene adds in the reaction flask, 80 degrees centigrade down heating stirred 30 minutes, slowly drip (10ml) SOCl 2, mix dropwise after, continued stirring reaction 4 hours.Decompression steams unreacted SOCl 2With the about 4ml of the mixture of solvent.Keep reacting liquid temperature below 30 degree, add 1,2-hexylene glycol (2ml) and 6ml (60mmol) N, accelerine was in room temperature reaction 2 hours.(3 * 50ml) extractions are with NaHCO with ether 3Solution washing filters, and through anhydrous magnesium sulfate drying, the pressure reducing and steaming solvent gets the 22.8g white solid matter, yield 70% with the ether extraction liquid that merges.Nuclear magnetic data ( 1HMR, 300MHZ, interior mark TSM, solvent DMSO), δ ppm 1.75 (4H, m), 4.25 (4H, m), 7.1-7.2 (6H, m).
Example 2: the preparation of compound 54
Figure A20071000303000212
At room temperature, 18.6g (60mmol) 2-[(4,6-dimethoxypyridin-2-yl) oxo]-the 6-chloro-benzoic acid adds in the reaction flask, and to wherein adding tetrahydrofuran (THF) (400ml) and 1,2-propylene glycol (2ml) is at N 2Protection under, and keep reaction system to be lower than 0 ℃, drip the 10ml sulfur oxychloride.After dropwising, heating reflux reaction 4 hours.(3 * 50ml) extractions are with NaHCO with ether 3Solution washing filters, and through anhydrous magnesium sulfate drying, the pressure reducing and steaming solvent gets the 22.8g white solid matter, yield 70% with the ether extraction liquid that merges.Nuclear magnetic data ( 1HMR, 300MHZ, interior mark TSM, solvent DMSO), δ ppm2.2 (2H, m), 4.25 (2H, m), 6.7-7.2 (6H, m).
Formulation examples 1
10 parts of No. 5 compounds, 6 parts of polyoxyethylene alkane aryl oxides, 4 parts of pelopon A parts, 50 parts of 30 parts of dimethylbenzene and pimelinketone are levigate and fill and strive mixing, promptly get 10% missible oil.
Formulation examples 2
50 parts of No. 65 compounds, 5 parts of polyoxyethylene alkane aryl oxides, 5 parts of pelopon A parts, 40 parts of levigate and abundant mixings of artificial hydrated SiO 2 promptly get 50% wettable powder.
Biological activity determination
With broadleaf weeds Cassia tora (Cassia tora), piemarker (Abutilon theophrasti), youth-and-old-age (Zinnia elegans Jacq), monocotyledon weed barnyard grass grass (Echinochloa crus-galli), lady's-grass (Digtaria sanguinalis), Herba Setariae Viridis (Setaria viridis), with crop such as soybean, potato, peanut be tested object, above-claimed cpd is measured.
According to follow procedure each compound is measured.
Measure behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing.Select size, the consistent examination material of growing stage, handle, processing places the greenhouse and waters.The examination material with compound treatment does not compare.
Testing compound is with suitable solvent (generally using acetone) dissolving, the processing of spraying then, and spouting liquid is 187 or the 468L/ hectare, effective dose is g/ha.In the 2 or 4 week investigation of processing back, with the 0-100 classification, 0 represents non-activity to medicament to each activity of trying material, and 100 expressions suppress fully.
At 600g/ha partial test result (the 2nd, 5,15,46,77,86,94,108,110,141, No. 161 compound), to broad leaf crop such as cotton safety.
The partial test compound to seedling after weed control efficacy see Table 3:
Compound Dosage g/ha The barnyard grass grass Lady's-grass Herba Setariae Viridis Cassia tora Piemarker Youth-and-old-age
2 300 100 100 100 100 100 100
5 300 100 100 100 100 100 100
15 300 100 100 100 100 100 100
46 300 100 100 100 100 100 100
77 300 100 100 100 100 100 100
86 300 100 100 100 100 100 100
94 300 100 100 100 100 100 100
108 300 100 100 100 100 100 100
110 300 100 100 100 100 100 100
141 300 100 100 100 100 100 100
161 44.5 100 81 84 88 90 84
174 300 100 100 100 100 100 100
180 44.5 86 78 89 96 98 88
184 300 100 100 100 100 100 100

Claims (5)

1. a general formula is
Figure A2007100030300002C1
Compound, in the formula:
In the formula:
R is H, halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group, (wherein said phenoxy group can be by the halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group for particularly C1-C4 alkyl, or phenoxy group, particularly the C1-C4 alkoxyl group replaces, or lower alkoxy, particularly C1-C4 alkoxyl group replace), or (not) replaces fragrant heterocycle;
A, B, C and D can be identical or different, and each is hydrogen atom naturally, such as the halogen atom of fluorine, chlorine, bromine or iodine, and low alkyl group, particularly C1-C4 alkyl, lower alkoxy, particularly C1-C4 alkoxyl group or halogenated lower alkoxy;
X is O, S, NCHO or CH 2
Y is O or N;
R ' is that (not) replaces C 1-C 18Alkylidene group, (not) replaces C 3-C 8Cycloalkylidene, (not) replaces C 2-C 18Alkenylene, (not) replaces C 3-C 8Inferior cycloalkenyl group, (not) replaces C 2-C 18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C 1-C 18Inferior assorted alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains carbonyl that (not) replaces 1-C 18Alkylidene group, the C that contains amido that (not) replaces 1-C 18Alkylidene group, the C that contains alkylsulfonyl that (not) replaces 1-C 18Alkylidene group, (not) replace contains sulfonic C 1-C 18Alkylidene group etc.;
2. according to claim 1, it is characterized in that: in formula (I) compound,
R is the halogen atom such as fluorine, chlorine, bromine or iodine of 6 replacements on phenyl ring, low alkyl group, C1-C4 alkyl particularly, or phenoxy group (wherein said phenoxy group can be by the halogen atom such as fluorine, chlorine, bromine or iodine, low alkyl group, particularly C1-C4 alkoxyl group replace, or lower alkoxy, particularly the C1-C4 alkoxyl group replaces), or (not) replaces fragrant heterocycle;
X is O or S;
Y is O;
R ' is that (not) replaces C 1-C 18Alkylidene group, (not) replaces C 3-C 8Cycloalkylidene, (not) replaces C 2-C 18Alkenylene, (not) replaces C 3-C 8Inferior cycloalkenyl group, (not) replaces C 2-C 18That alkynylene, (not) replace is nitrogenous, oxygen, sulphur C 1-C 18Inferior assorted alkyl, (not) substituted aryl, (not) replaces fragrant heterocycle, the C that contains carbonyl that (not) replaces 1-C 18Alkylidene group, the C that contains amido that (not) replaces 1-C 18Alkylidene group, the C that contains alkylsulfonyl that (not) replaces 1-C 18Alkylidene group, (not) replace contains sulfonic C 1-C 18Alkylidene group etc.;
3. the purposes of the described compound of claim 1 aspect management of weeds.
4. opposing method for weed is characterized in that: make activeconstituents according to claim 1 act on the weeds or on its habitat.
5. prepare the method for weedicide, it is characterized in that: will mix with solvent and tensio-active agent according to the activeconstituents of claim 1.
CN 200710003030 2007-01-31 2007-01-31 Pyrimidine salicylic acid cluster molecule with herbicide activity Pending CN101007799A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104610249A (en) * 2014-12-25 2015-05-13 中国农业科学院植物保护研究所 Bi-titer sulfonyl isoxazole derivative and application thereof
CN104610248A (en) * 2014-12-25 2015-05-13 中国农业科学院植物保护研究所 Multi-titer sulfonyl triazole compounds and application thereof
WO2025185364A1 (en) * 2024-03-06 2025-09-12 浙江大学 Pyrimidine-biaryl compounds, preparation method therefor and use thereof as herbicides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104610249A (en) * 2014-12-25 2015-05-13 中国农业科学院植物保护研究所 Bi-titer sulfonyl isoxazole derivative and application thereof
CN104610248A (en) * 2014-12-25 2015-05-13 中国农业科学院植物保护研究所 Multi-titer sulfonyl triazole compounds and application thereof
CN104610249B (en) * 2014-12-25 2017-09-15 中国农业科学院植物保护研究所 A kind of two potency sulfonyl isoxazole derivates and its application
CN104610248B (en) * 2014-12-25 2018-07-20 中国农业科学院植物保护研究所 A kind of multiple-effect valence sulfonyl triazoles class compound and its application
WO2025185364A1 (en) * 2024-03-06 2025-09-12 浙江大学 Pyrimidine-biaryl compounds, preparation method therefor and use thereof as herbicides

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