CN100411516C - Carbaminate herbicide - Google Patents
Carbaminate herbicide Download PDFInfo
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- CN100411516C CN100411516C CNB2006100989391A CN200610098939A CN100411516C CN 100411516 C CN100411516 C CN 100411516C CN B2006100989391 A CNB2006100989391 A CN B2006100989391A CN 200610098939 A CN200610098939 A CN 200610098939A CN 100411516 C CN100411516 C CN 100411516C
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- herbicide
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- sulphur grass
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Abstract
The present invention is carbaminate herbicide, and belongs to the field of farm chemical technology. In order to raise the herbicidal effect and activity of asulam herbicide, the present invention alters and optimizes the structure of asulam compound as precursor compound to obtain the new herbicide. The present invention is used main for farm field, orchard, tea garden, wood land, etc to prevent and kill most of monocotylous and dicotylous weeds, such as fixweed, Indian mallow, speedwell, etc.
Description
Technical field
The present invention is a chloropropham, belongs to agricultural chemicals, is mainly used in to weed a garden.
Background technology
The development of agricultural chemicals, develop towards efficient, safety, economy, non-harmful direction, some high toxicities, high residue, the agricultural chemicals of severe environmental pollution is eliminated in succession, and the pesticide new variety of environmentally friendly, super-high-efficient, high selectivity, low price is subjected to people's favor.The outstanding feature of world's pesticide developing is to emphasize the highly active while at present, more pays attention to safety, guarantees non-target organism, the mankind and environmentAL safety, and the trend that has safety first, activity to take second place, and the exploitation of weed killer herbicide is no exception.Herbicide action mechanism mainly is to suppress and the normal physiology course of blocking-up plant, causes the primary biophysics and the biological chemistry action of weeds death.Promptly mainly be some crucial biophysics and biological chemistry action in inhibition or the interference growing process, cause the destruction and the termination of process of growth, make plant death.The key effect that is suppressed generally is photosynthesis, respiration, biochemistry is synthetic and plant growing.
China is imitated from agricultural chemicals, progressively go on the initiative of novel pesticide, but the initiative work of China's weed killer herbicide only is the starting stage.From the weed killer herbicide of having developed, as lead compound, carry out structural change, thereby develop the new varieties that chemical constitution is different from former compound, reach and improve active and the expansion scope of application.
U.S. Pat 3823008 and US 3121042 have reported the spirit of a kind of chloropropham sulphur grass, to be nineteen sixty-eight developed and through the development in 10 years, the spirit of sulphur grass was widely used in American-European countries such as Canada, the U.S. and Britain by May and Baker company (now being Sanofi-Aventis) for it.But after the eighties, along with the arrival in highy potent herbicide epoch, sulphur grass miraculous cure effect is outstanding, activity is low, consumption is big, has influence on extensive use.
Summary of the invention
Purpose of the present invention overcomes disadvantages of background technology exactly, designs that a kind of drug effect is outstanding, active height and the little chloropropham of consumption.
Design of the present invention: select for use the spirit of sulphur grass as lead compound; sulphur grass etherealize laminate structures is optimized initiative; at first active from improving; the amino acylation reaction of sulphur grass etherealize compound is generated acetamide; electron conjugated by nitrogen on the amino of acidylate and carbonyl, form second activated centre.Connect the chlorobenzene ether that root, stem, leaf absorption conduction enhancing and drug effect are improved in addition on the alkyl of acetamide, it becomes the mapping structure with original methyl ether, and the effect of chlorobenzene ether is far longer than the effect of methyl ether.The sulphur grass spirit of process optimization, except amino acidylate improved activity and chlorobenzene ether raising drug effect, the enantiomer-specific structure after the optimization was the center mapping, and the effect of Synergistic is arranged.
The present invention is a kind of chloropropham, and its characteristics are that structural formula is:
Wherein R is Cl or CH
3
The preferred chloropropham of the present invention, its characteristics are that structural formula is:
Advantage of the present invention:
1, activity of weeding of the present invention is significantly higher than the activity of weeding of sulphur grass spirit.The present invention is under 20ppm and 100ppm concentration, and to broadleaf weed descurainia sophia (l.) webb ex prantl, piemarker, Veronica, the inhibiting rate of monocotyledon weed perennial ryegrass, wild oat root and height of seedling all is higher than the clever inhibiting rate to weeds root and height of seedling of sulphur grass under the same concentrations.
2, using dosage of the present invention is less than the using dosage of sulphur grass spirit.The present invention is under the 133 gram/mus at using dosage, and broadleaf weed descurainia sophia (l.) webb ex prantl, piemarker, Veronica and the monocotyledon weed perennial ryegrass of 2-3 leaf phase, the control efficiency of wild oat are reached more than 90%.
3, the present invention can be used as the broad-spectrum herbicide use.The present invention can effectively prevent and kill off most of single, double cotyledon weeds such as descurainia sophia (l.) webb ex prantl, piemarker, Veronica, perennial ryegrass, wild oat, lamb's-quarters, humulus grass, field thistle, artemisia annua.
Embodiment:
Embodiment 14-(2-methyl-4-chloro-benzene oxygen acetylamino) benzenesulfonamido-methyl formate is synthetic
1.1 the present invention implements with reference to following synthetic route
In the there-necked flask of 1000ml, add the 500ml carbon tetrachloride, add 2-methyl-4-chloro-phenoxy acetic acid 80.0g (0.4 mole), heat to 40 ± 2 ℃, then Dropwise 5 3.6g (0.45 mole) thionyl chloride, be warming up to 60 ± 2 ℃ after dripping off, react after 4 hours; Add sulfanilyl radical methyl carbamate 92.0g (0.4 mole), 75 ± 2 ℃ of insulation reaction 4 hours; Carbon tetrachloride is removed in decompression, adds 150ml methyl alcohol then, at room temperature stirs and separates out white solid in 10～30 minutes, and filtration, drying obtain 143g 4-(2-methyl-4-chloro-benzene oxygen acetylamino) benzenesulfonamido-methyl formate.
1.2 structure is identified
Fusing point:
184～186℃
Elementary analysis:
Measured value C%49.50 H%4.16 N%6.83
Theoretical value C%49.46 H%4.15 N%6.79
Infrared spectrum:
IR(cm
-1)：3393(ArN-H)，3190(SO
2N-H)，1746(C＝O，C-CONH-Ar)，1688(C＝O，CO
2)，1359，1165(SO
2)。
Magnetic resonance spectroscopy:
1H-NMR(δppm)：2.242(3H，j)，3.566(3H，i)，4.802(2H，d)，6.889(1H，c)，7.184(1H，b)，7.202(1H，a)，7.811～7.877(4H，f，g)，10.572(1H，e)，11.999(1H，h)。
Embodiment 2 4-(2,4 dichloro benzene oxygen acetylamino) benzenesulfonamido-methyl formate is synthetic
2.1 the present invention implements with reference to following synthetic route:
In the there-necked flask of 1000ml, add the 500ml chloroform, add 2,4-dichlorphenoxyacetic acid 121.6g (0.55 mole), heat to 60 ± 2 ℃, drip 60.0ml (0.55 mole) thionyl chloride, drip off back insulation reaction 1 hour, add sulfanilyl radical methyl carbamate 126.2g (0.5 mole) then and be warmed up to 60 ± 2 ℃, insulation reaction is after 3 hours; Chloroform is removed in decompression, adds the 150ml absolute ethyl alcohol, at room temperature stirs and separates out white solid in 10～30 minutes, filters, and drying obtains 182g 4-(2,4 dichloro benzene oxygen acetylamino) benzenesulfonamido-methyl formate.
2.2 structure is identified
Fusing point: 188 ℃～190 ℃
Elementary analysis:
Measured value C%42.93 H%3.21 N%6.47
Theoretical value C%44.25 H%3.48 N%6.45
Infrared spectrum:
IR(cm-1)：3377(ArN-H)，3227(SO
2N-H)，1744(C＝O，C-CONH-Ar)，1693(C＝O，CO
2)，1355，1161(SO
2)。
Magnetic resonance spectroscopy:
1H-NMR(δppm)：3.5819(3H，i)，4.9627(2H，d)，7.1500(1H，c)，7.3742(1H，b)，7.5939(1H，a)，7.8858(4H，f，g)，10.7393(1H，e)，12.0375(1H，h)。
Carry out the biological activity determination test with the compound (MCRI-P-1) of embodiment 1 preparation and the compound (MCRI-P-2) of embodiment 2 preparations below.
1, active culture ware method activity of weeding test
With MCRI-P-1, MCRI-P-2 and the agent of sulphur grass Lingshui Spring is 100ppm, 20ppm liquid with the clear water dilution respectively.At diameter is pad one deck filter paper in the culture dish of 90mm, adds the soup after the 5ml dilution, will urge descurainia sophia (l.) webb ex prantl, piemarker, Veronica, perennial ryegrass, each 20 culture dish of putting into variable concentrations respectively of wild oat seed of bud again.Cover ware lid, culture dish is put into 25 ± 2 ℃ natural lighting and cultivated between cultivating by the plumule incline direction 15 ° of angles that tilt.5 repetitions are established in every processing in the test, are contrast with the clear water.After four days, root length, the stem of measuring plant are long, calculate the long percentage that suppresses of root length, stem of the different down examination materials of variable concentrations.Measurement result sees Table 1.
Table 1 active culture ware method activity of weeding measurement result
Find out from table 1 activity of weeding measurement result, under 20ppm and 100ppm concentration, MCRI-P-1 of the present invention and MCRI-P-2 are to broadleaf weed descurainia sophia (l.) webb ex prantl, piemarker, Veronica, and the inhibiting rate of monocotyledon weed perennial ryegrass, wild oat root and height of seedling all is higher than the clever inhibiting rate to weeds root and height of seedling of sulphur grass under the same concentrations.
Under same concentrations, MCRI-P-1 and MCRI-P-2 are significantly higher than the spirit of sulphur grass to the root of broadleaf weed descurainia sophia (l.) webb ex prantl, piemarker, Veronica and monocotyledon weed perennial ryegrass, wild oat and the inhibiting rate of height of seedling, thereby MCRI-P-1 and MCRI-P-2 are significantly higher than the spirit of sulphur grass to the activity of weeding for the examination weeds.
2, greenhouse pot culture method activity of weeding test
The loam of in the dixie cup of sectional area 3.85 * 10-7m2, packing into and sieving, first water is drenched, and plants 20 descurainia sophia (l.) webb ex prantl of having sprouted, piemarker, Veronica, perennial ryegrass and bromegrass seeds respectively, and the sowing depth crop is 2 centimetres.Treat 2～3 leaf phases of plant, carry out the cauline leaf spraying and handle.The aqua of MCRI-P-1 and MCRI-P-2 is established 66.7 gram/mus and two processing of 133.3 gram/mus respectively, is contrast with sulphur grass Lingshui Spring agent 133.3g gram/mu and clear water, and 25 ± 2 ℃ natural lighting glass room is put in 3 repetitions of every processing, 3 repetitions of every processing.After 20 days, cut the acrial part fresh weight, calculate the fresh weight preventive effect.Result of the test sees Table 2.
The potted plant cauline leaf Processing Test of table 2 result
Find out that from table 2 pot-culture method activity of weeding result of the test under the using dosage of 133 gram/mus, MCRI-P-1 and MCRI-P-2 all are significantly higher than the spirit of sulphur grass to the control efficiency of broadleaf weed descurainia sophia (l.) webb ex prantl, piemarker, Veronica and monocotyledon weed perennial ryegrass, bromegrass.
3, sub-district, land for growing field crops weeding test
In the vacant lot of outdoor selection weeds kind and growing way basically identical as small plot experiment ground, weeds 4-8 leaf phase in the sub-district.MCRI-P-1, MCRI-P-2 and sulphur grass Lingshui Spring agent 500 gram/mus and clear water contrast totally 4 processing are established in test.Handle 1 sub-district for 1, sub-district area 25m2, each district's group randomized arrangement, each is handled and repeats 3 times.Adopt the workers and peasants-16 type knapsack hand sprayer processing cauline leaf of manually spraying, 30 kilograms/mu of water consumptions.Weeded out the rank grass in the 30th day behind the medicine, calculate the fresh weight preventive effect.Result of the test sees Table 3.
Table 3 land for growing field crops sub-district weeding result of the test
Find out that from table 3 land for growing field crops sub-district weeding result of the test under the dosage of 500 gram/mus, MCRI-P-1 reaches 100% to the control efficiency of broadleaf weed lamb's-quarters, humulus grass, artemisia annua and Veronica, the control efficiency of field thistle has also been reached 98.7%; MCRI-P-2 reaches 100% to the control efficiency of broadleaf weed lamb's-quarters, humulus grass, and the control efficiency of field thistle, artemisia annua and Veronica is respectively 89.7%, 85.7% and 50.1%, all is significantly higher than the spirit of sulphur grass.MCRI-P-1 of the present invention and MCRI-P-2 are significantly higher than the spirit of sulphur grass to great majority for the control efficiency of trying weeds.
Claims (2)
1. chloropropham is characterized in that structural formula is:
Wherein R is Cl or CH
3
2. chloropropham according to claim 1 is characterized in that structural formula is:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100989391A CN100411516C (en) | 2006-07-18 | 2006-07-18 | Carbaminate herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100989391A CN100411516C (en) | 2006-07-18 | 2006-07-18 | Carbaminate herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1899041A CN1899041A (en) | 2007-01-24 |
| CN100411516C true CN100411516C (en) | 2008-08-20 |
Family
ID=37655178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100989391A Expired - Fee Related CN100411516C (en) | 2006-07-18 | 2006-07-18 | Carbaminate herbicide |
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|---|---|
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313847A (en) * | 1978-06-15 | 1982-02-02 | Ici Americas Inc. | Surfactant compositions |
| US4541860A (en) * | 1980-06-06 | 1985-09-17 | Montedison S.P.A. | Stable compositions of N-(3,4-dichlorophenyl)-N'-methoxy-N'-methylurea (linuron) and 2,6-dinitro-N,N-dipropyl-4-trifluoro-methylaniline (trifluralin) in emulsion |
| CN1330593A (en) * | 1998-12-16 | 2002-01-09 | 西巴特殊化学品控股有限公司 | Heat sensitive recording material |
-
2006
- 2006-07-18 CN CNB2006100989391A patent/CN100411516C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313847A (en) * | 1978-06-15 | 1982-02-02 | Ici Americas Inc. | Surfactant compositions |
| US4541860A (en) * | 1980-06-06 | 1985-09-17 | Montedison S.P.A. | Stable compositions of N-(3,4-dichlorophenyl)-N'-methoxy-N'-methylurea (linuron) and 2,6-dinitro-N,N-dipropyl-4-trifluoro-methylaniline (trifluralin) in emulsion |
| CN1330593A (en) * | 1998-12-16 | 2002-01-09 | 西巴特殊化学品控股有限公司 | Heat sensitive recording material |
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| Publication number | Publication date |
|---|---|
| CN1899041A (en) | 2007-01-24 |
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