CN101223883B - Weedicide compound of water dissolved saline of novel structure sulfonylurea compound - Google Patents
Weedicide compound of water dissolved saline of novel structure sulfonylurea compound Download PDFInfo
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- CN101223883B CN101223883B CN2007101511555A CN200710151155A CN101223883B CN 101223883 B CN101223883 B CN 101223883B CN 2007101511555 A CN2007101511555 A CN 2007101511555A CN 200710151155 A CN200710151155 A CN 200710151155A CN 101223883 B CN101223883 B CN 101223883B
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- monosulfmeturon
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- water
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- 229940100389 Sulfonylurea Drugs 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 18
- -1 sulfonylurea compound Chemical class 0.000 title claims abstract description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 title description 5
- 239000011780 sodium chloride Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000000843 powder Substances 0.000 claims abstract description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 244000062793 Sorghum vulgare Species 0.000 claims abstract description 5
- 235000019713 millet Nutrition 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 3
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 3
- 238000009333 weeding Methods 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012467 final product Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002689 soil Substances 0.000 abstract description 11
- 239000004009 herbicide Substances 0.000 abstract description 5
- 240000008042 Zea mays Species 0.000 abstract description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 4
- 244000105624 Arachis hypogaea Species 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract description 3
- 241000219146 Gossypium Species 0.000 abstract description 3
- 241000209140 Triticum Species 0.000 abstract description 3
- 235000021307 Triticum Nutrition 0.000 abstract description 3
- 230000006378 damage Effects 0.000 abstract description 3
- 235000020232 peanut Nutrition 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 208000018380 Chemical injury Diseases 0.000 abstract 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract 1
- 239000013043 chemical agent Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 235000009973 maize Nutrition 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 description 26
- 230000000694 effects Effects 0.000 description 7
- 244000237956 Amaranthus retroflexus Species 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 238000010276 construction Methods 0.000 description 5
- 230000003449 preventive effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000857 drug effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 244000037666 field crops Species 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
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Abstract
The invention relates to a herbicide composition of water soluble salt of a sulfonylurea compound, and comprises compounds with effective active ingredients in a structure (I), wherein, R1 indicates NO2, Cl, CH3, F, Br, I, etc.; R2 indicates CH3, CH3O, F, Cl, Br, I or NO2; M represents Na, K, Mg, Ca, Mn, Zn, Cu, Fe, etc. and L represents H2O, methanol, ethanol, DMSO, etc. The effective active ingredients of the invention has excellent herbicidal activity and can be dissolved in water as well as provide good conditions for processing the composition into agents such as environment-friendly soluble powder or liquid agent, etc. In addition, the invention has better selectivity for crops such as wheat, maize, millet, cotton, peanuts, etc. in the north of China and causes no chemical injury tothe crops due to the movement of chemical agent when in use or after use and significantly reduces the damage of chemical residue in soil to crops.
Description
Technical field
The present invention relates to a kind of water dissolved saline of novel structure sulfonylurea compound herbicidal composition.
Background technology
All has disubstituted architectural feature on the heterocycle of commercial sulfonylurea herbicide kind in its molecule.The G.Levitt of du pont company particularly points out, the sulfonylureas molecule must be at 4 of its heterocyclic moiety, all there is substituting group enough activity of weeding just to be arranged on 6 two positions (referring to Synthesis and Chemistry of Agrochemicals II, ACSSymposium Series No.443, Washington DC:American Chemistry Society, 1991,16-31).The compound that U.S. Pat 5160365, US 5591694 and US6228808 have reported the following formula structure is as weed killer herbicide:
Chinese patent CN 1080116A discloses following formula: compound as corn field herbicide, and pyrimidine ring is single the replacement in its molecule.
Chinese patent CN 1106393A discloses following general formula solsonylurea compounds, but detailed biological activity test result, concrete application and the application dose of unexposed wherein all compounds:
Summary of the invention
The object of the present invention is to provide a kind of herbicidal composition (monosulfmeturon water-soluble salt herbicidal composition) of water dissolved saline of novel structure sulfonylurea compound, it has very high activity of weeding to broad leaved weeds, can directly be used in the field weeding in land for growing field crops.Extensively wheat, corn, millet, cotton, the peanut and other crops of plantation all have selectivity preferably because to northern China, this compound in use reaches and uses the difficult poisoning that causes above-mentioned crop of moving because of medicament in back, has also greatly reduced the injury of pedo relict to crops simultaneously.
A kind of water dissolved saline of novel structure sulfonylurea compound provided by the invention, its structure are that metal is not connected on the nitrogen of sulfonyl, but are connected the oxygen, ketonic oxygen, hydrone of sulfonyl, (as accompanying drawing 2) on the nitrogen of the ketonic oxygen of a part and pyrimidine ring in addition.And among the CN 20051013223.2 in the sulfonylurea compound water-soluble salt, Na is that the N that links to each other with sulfonyl on the sulfonylureas bridge directly links to each other:
The present invention is the herbicidal composition that comprises the compound water-soluble salt of effective active component structure (I):
Wherein, M is Na, K, Mg, Ca, Mn, Zn, Cu, Fe etc.; R
1: NO
2, Cl, CH
3, F, Br, I etc.; R
2: CH
3, CH
3O, F, Cl, Br, I, NO
2Deng; L is H
2O, methyl alcohol, ethanol, DMSO etc.
The present invention is the herbicidal composition of compound (II) water-soluble salt that comprises effective active component, that is: N-[2 '-(4-methyl)-pyrimidine radicals]-herbicidal composition of 2-nitrobenzene sulfonylureas water-soluble salt, the structure of compound (II) is:
Wherein M be Na, K, etc., L is H
2O.
The present invention comprises that also agricultural goes up the acceptable carrier: water, talcum powder, clay, kaolin, algae tripoli, lignin, sodium lignin sulfonate, lauryl sodium sulfate, hydro carbons, ethers, ketone, arene, amide-type and surfactant, emulsifier etc.
Containing effective active component in the composition of the present invention is 0.1-99% (weight), is preferably 1-95% (weight), and the consumption of effective active composition is that the amount that adopts this area professional to use always is as the criterion.
But the present invention can make wet-milling, and aqua and the various formulations of soluble powder etc. can also add synergist, stabilizing agent or carry out compositely with other effective active composition, can improve the drug effect of composition and the practicality on the agricultural greatly.
The preparation method of new construction water-soluble salt herbicidal composition of the present invention is with effective active composition N-[2 '-(4-methyl)-pyrimidine radicals]-2-nitrobenzene sulfonylureas water-soluble salt is direct to mix according to a conventional method with the last acceptable carrier of agricultural.
The step that the preparation method of The compounds of this invention (I) comprises is at 0 ℃--under 60 ℃ of temperature with the hydroxide of equimolar solsonylurea compounds and corresponding salt or oxide in organic solvent stirring reaction 10-24 hour, reduce the temperature to room temperature, add entry, separatory, the water layer precipitation obtains pressed powder, gets white crystal with recrystallizing methanol and gets final product.The reaction temperature optimum temperature is at 15 ℃--and 35 ℃.Solvent should be selected non-protonic solvent, as acetonitrile, acetone, 1,4-dioxane, carrene, chloroform, 1,2-dichloroethane, oxolane or their mixture.
The preparation method of The compounds of this invention (II) is with equimolar N-[2 '-(4-methyl)-pyrimidine radicals under the room temperature]-2-nitrobenzene sulfonylureas and sodium hydroxide or potassium hydroxide stirred in carrene 16 hours, add entry, separatory, the water layer precipitation obtains pale yellow powder, gets white needle-like crystals with recrystallizing methanol and gets final product.
The application of the present composition is that an amount of present composition is imposed on the crop Tanaka that will cut weeds with conventional method, and these methods comprise soil and active component leaf surface treatment etc.The soil table was sprayed before effective amount of actives compound (I) also was applied to broadcast the back seedling, or cauline leaf is handled behind the seedling, can effectively prevent and kill off broad leaved weeds.The common 0.5-4g active component of amount described here/mu is preferably 1-3g/ mu.
The present invention uses the compound (I) of effective dose that broad leaved weed is had good active, can directly be used in the field weeding in land for growing field crops.Extensively wheat, corn, millet, cotton, the peanut and other crops of plantation all have selectivity preferably, particularly millet field weeding because to northern China.This compound in use reaches and uses the difficult poisoning that causes above-mentioned crop of moving because of medicament in back, has also greatly reduced the injury of pedo relict to crops simultaneously.
The present invention has very high activity of weeding to broad leaved weeds, give birth to the survey data and show that the activity of weeding of the sulfonylurea compound water-soluble salt of new construction is significantly higher than its parent solsonylurea compounds, give birth to the survey result and show that monosulfmeturon sodium salt drug effect is better than monosulfmeturon, some test result can exceed 1-2 doubly.The solvability of its sodium salt in water is about 60g/L under the normal temperature, because it has the water-soluble then easier various formulations of pesticide that are processed into, this is processed into environment amenable various formulation just for this medicine good condition is provided, and reduces cost, for industrialization and marketing have brought wide prospect.
Substantive distinguishing features of the present invention can be embodied from following embodiment, but these embodiment only as an illustration, rather than limits the invention.
Description of drawings
Fig. 1 is monosulfmeturon construction unit figure.
Fig. 2 monosulfmeturon sodium salt of the present invention construction unit figure.
Fig. 3 monosulfmeturon sodium salt of the present invention nuclear magnetic spectrogram
Fig. 4 monosulfmeturon sodium salt of the present invention infrared spectrum
Fig. 5 monosulfmeturon sodium salt of the present invention uv atlas
Fig. 6 monosulfmeturon sodium salt of the present invention high resolution mass spectrum figure
Fig. 7 monosulfmeturon sodium salt of the present invention mass spectrogram
Sulfonylurea compound water-soluble salt construction unit figure among Fig. 8 CN 20051013223.2
Embodiment
Embodiment 1: monosulfmeturon of the present invention (N-[2 '-(4-methyl)-pyrimidine radicals]-2-nitrobenzene sulfonylureas) synthetic method of sodium salt
Weighing 0.05mol monosulfmeturon (16.85g) and 0.05mol (2g) sodium hydroxide powder add in the 100mL carrene, and stirring at room 16 hours adds that 100mL is water-soluble to be separated; Separatory, the water layer precipitation obtains pale yellow powder, gets white needle-like crystals with recrystallizing methanol, is monosulfmeturon sodium salt of the present invention.Fusing point is 192～193 ℃, yield: 95%.
Its structure through elementary analysis and IR,
1HNMR, MS and X-ray crystal diffraction characterize.The elementary analysis measured value is C:37.97%, H:3.28%, N:18.48%; Theory is calculated as C:38.20%, H:3.21%, and N:18.56% is all in the experimental error scope;
1HNMR (DMSO-d
6) the δ value is respectively 2.31 (s, 3H, Pyrimidine-CH
3); 6.81 (d, 1H, Pyrimidine-H); 7.60-8.12 (m, 4-H, Ph-H); 8.30 (d, 1H, Pyrimidine-H); 8.74 (s, 1H, CO-NH); IR (υ/cm
-1, pressing potassium bromide troche): 3540 (υ N-H); 1647 (υ NO2); 1516 (υ Ph-H); 1594 (υ Ph-H); 1455 (υ Ph-H); 1250 (υ SO2); 1155 (υ SO2), the characteristic absorption of structure all appears in infrared spectrum; It is 382.17 that corresponding M+Na peak appears in MS.UV scanning finds that product monosulfmeturon sodium salt has uv absorption at 190-300nm, and maximum absorption wavelength is at 199.50nm and 239.00nm place.X-ray crystal diffraction is measured an oxygen atom, carbonylic oxygen atom of Na and sulfonylureas sulfonyl, the oxygen atom of nitrogen-atoms on a part sulfonylureas pyrimidine ring and carbonylic oxygen atom, water of crystallization links to each other in addition.
Embodiment 2: the comparison of monosulfmeturon and monosulfmeturon sodium salt activity of weeding of the present invention
The greenhouse pot culture test of pesticide effectiveness
Carry out following test with embodiment 1 obtained compound (I):
In the plastics cuvette of diameter 8cm, put into a certain amount of soil and water routinely, plant lady's-grass (Digitariasanguinalis), barnyard grass grass (Echinochloa crusgalli), three-coloured amaranth (Amaranthus retroflexus) and lamb's-quarters (Chenopodium album) respectively, in greenhouse, cultivate, cover with plastics before coming up.Manage routinely, every day, in addition quantitative clear water was to keep normal growth.Handle with the monosulfmeturon and the monosulfmeturon sodium salt of the present invention of 0.208,0.5,1.0,2.0,4.0 gram/mu dosage respectively, handle and to comprise two kinds of soil treatment (before emerging) and cauline leaf (one heart stage of seedling one leaf) processing.20 days " Invest, Then Investigate " results measure the overground part fresh weight, suppress percentage with fresh weight and represent drug effect.
Active graded index: A level: 〉=80%; B level: 60～79%; C level: 40～59%; D level :≤39%.
Data are handled: adopt biologicall test scalar type modem value analytical method calculating ED in DPS (8.01) software
50, ED
90
Table 1, monosulfmeturon and monosulfmeturon sodium salt activity of weeding of the present invention be (inhibition percentage) relatively
| Sample | Dosage (gram/mu) | The barnyard grass grass | Rape | Lady's-grass | Amaranthus retroflexus | ||||
| Soil | Cauline leaf | Soil | Cauline leaf | Soil | Cauline leaf | Soil | Cauline leaf | ||
| Monosulfmeturon | 0.208 | 20.7 | 0 | 40.4 | 85.7 | 0 | 0 | 48.5 | 100 |
| 0.5 | 21.5 | 0 | 59.8 | 88.4 | 17.1 | 0 | 67.2 | 100 | |
| 1.0 | 22.0 | 0 | 67.5 | 100 | 19.8 | 0 | 73.9 | 100 | |
| 2.0 | 23.9 | 8.5 | 84.6 | 100 | 25.3 | 31.2 | 77.3 | 100 | |
| 4.0 | 35.5 | 55.7 | 91.7 | 100 | 29.0 | 61.9 | 86.0 | 100 | |
| The monosulfmeturon sodium salt | 0.208 | 10.2 | 0 | 64.6 | 80.3 | 9.7 | 0 | 63.2 | 90.9 |
| 0.5 | 12.6 | 0 | 81.2 | 86.6 | 16.1 | 0 | 74.6 | 100 | |
| 1.0 | 14.0 | 2.5 | 81.5 | 100 | 19.8 | 0 | 80.6 | 100 | |
| 2.0 | 33.3 | 36.9 | 90.3 | 100 | 26.3 | 73.3 | 83.3 | 100 | |
| 4.0 | 57.5 | 87.3 | 96.0 | 100 | 45.6 | 78.9 | 90.0 | 100 | |
Table 2, monosulfmeturon and monosulfmeturon sodium salt activity of weeding of the present invention be (lethal dose, soil treatment) relatively
| Prevent and kill off object | Sample | ED 50 | ED 90 | Regression equation | R | ||
| (gram/mu) | 95% confidence limit | (gram/mu) | 95% confidence limit | ||||
| Rape | Monosulfmeturon | 0.34 | 4.17-6.27 | 3.49 | 41.64-65.82 | Y＝4.1007+1.2687X | 0.9926 |
| The monosulfmeturon sodium salt | 0.09 | 0.66-2.61 | 1.68 | 18.48-34.26 | Y＝4.8818+0.9992X | 0.9740 | |
| Amaranthus retroflexus | Monosulfmeturon | 0.19 | 1.82-4.32 | 7.22 | 65.47-179.10 | Y＝4.6384+0.8076X | 0.9815 |
| The monosulfmeturon sodium salt | 0.06 | 0.59-1.50 | 4.43 | 49.57-89.06 | Y＝5.0168+0.6940X | 0.9903 |
Test result:
Result of the test sees tables of data 1,2 for details.Table 1 data show that monosulfmeturon and monosulfmeturon sodium salt of the present invention are poor slightly to the preventive effect of two kinds of monocotyledon weed barnyard grass grass, lady's-grass, and the preventive effect of monosulfmeturon sodium salt of the present invention is better than monosulfmeturon during higher dosage; Monosulfmeturon and monosulfmeturon sodium salt of the present invention all had good preventive effect to rape and Amaranthus retroflexus when cauline leaf was handled, and preventive effect is suitable; In the test dose scope, monosulfmeturon sodium salt of the present invention is better than monosulfmeturon to the preventive effect of rape and Amaranthus retroflexus during soil treatment.More particularly bright this conclusion of the lethal dose data of table 2, monosulfmeturon sodium salt of the present invention is to the ED of rape and Amaranthus retroflexus
50And ED
90All significantly less than monosulfmeturon.
With 18 kilograms of monosulfmeturon sodium salts of the present invention, 0.4 kilogram of lauryl sodium sulfate, 0.6 kilogram of sodium lignin sulfonate, 1 kilogram of urea mixes, and pulverizes by 200 mesh sieves, is the present invention's 90% monosulfmeturon sodium salt soluble powder.
With 2 kilograms of monosulfmeturon sylvite of the present invention, 1.3 kilograms of calcium lignosulfonates, 0.2 kilogram of lauryl sodium sulfate, 0.8 kilogram sodium carbonate, 0.7 kilogram of sodium bicarbonate, 5 kilograms of urea mix, pulverize by 200 mesh sieves, be 20% monosulfmeturon sylvite soluble powder.
Claims (8)
1. the herbicidal composition of a sulfonylurea compound water-soluble salt is characterized in that comprising following formula structure (I) compound of effective active component:
Wherein, R
1: NO
2, Cl, CH
3, F, Br, I; R
2: CH
3, CH
3O, F, Cl, Br, I or NO
2M is Na, K, Mg, Ca, Mn, Zn, Cu or Fe; L is H
2O, methyl alcohol, ethanol or DMSO;
With acceptable carrier on the agricultural.
2. herbicidal composition according to claim 1 is characterized in that R
1Be NO
2R
2Be CH
3M is Na or K, and L is H
2O.
3. herbicidal composition according to claim 2 is characterized in that containing in the described composition described effective active composition and is: 0.1-99%, weight.
4. herbicidal composition according to claim 3 is characterized in that preferably containing in the described composition described effective active composition and is: 1-95%, weight.
5. the preparation method of herbicidal composition effective active empirical formula (I) compound of the described sulfonylurea compound water-soluble salt of claim 2, it is characterized in that comprising the steps: under 0 ℃ of-60 ℃ of temperature the hydroxide of equimolar solsonylurea compounds and corresponding salt or oxide in organic solvent stirring reaction 10-24 hour, reduce the temperature to room temperature, add entry, separatory, the water layer precipitation obtains pressed powder, gets white crystal with recrystallizing methanol and gets final product; Described solvent is selected non-protonic solvent: acetonitrile, acetone, 1,4-dioxane, carrene, chloroform, 1,2-dichloroethane, oxolane or their mixture.
6. the preparation method of the herbicidal composition effective active component cpd of the described sulfonylurea compound water-soluble salt of claim 2, it is characterized in that comprising the steps: under the room temperature with equimolar N-[2 '-(4-methyl)-pyrimidine radicals]-2-nitrobenzene sulfonylureas and sodium hydroxide or potassium hydroxide stirred in carrene 10-24 hour, add entry, separatory, the water layer precipitation obtains pale yellow powder, gets white needle-like crystals with recrystallizing methanol and gets final product.
7. the application of claim 1 or 2 described herbicidal compositions is characterized in that the described composition of effective dose is imposed on the weeding place.
8. the application of herbicidal composition according to claim 7 is characterized in that the described composition of effective dose is imposed on the weeding of millet field.
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|---|---|---|---|
| CN2007101511555A CN101223883B (en) | 2007-12-21 | 2007-12-21 | Weedicide compound of water dissolved saline of novel structure sulfonylurea compound |
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| CN101223883B true CN101223883B (en) | 2011-06-15 |
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|---|---|---|---|---|
| CN1675998A (en) * | 2005-03-21 | 2005-10-05 | 南开大学 | Herbicide composition of sulfonylurea compound water-soluble salt |
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