173159-57-4
2-[3-(4,6-Dimethoxy-2-pyrimidinyl)ureidosulfonyl]-4-(formamido)-N,N-dimethylbenzamide
CAS: 173159-57-4
Molecular Formula: C17H20N6O7S
173159-57-4 - Names and Identifiers
| Name | 2-[3-(4,6-Dimethoxy-2-pyrimidinyl)ureidosulfonyl]-4-(formamido)-N,N-dimethylbenzamide |
| Synonyms | aef130360 C17H20N6O7S foramsulfron FORAMSULFURON foramsulfuron(bsi,iso) GLYCEROKINASE FROM CANDIDA UTILIS 2-[3-(4,6-Dimethoxy-2-pyrimidinyl)ureidosulfonyl]-4-(formamido)-N,N-dimethylbenzamide 2-[3-(4,6-DIMETHOXY-2-PYRIMIDINYL)UREIDOSULFONYL]-4-(FORMAMIDO)-N,N-DIMETHYLBENZAMIDE 2-(N-((4,6-DiMethoxypyriMidin-2-yl)carbaMoyl)sulfaMoyl)-4-forMaMido-N,N-diMethylbenzaMide 2-(N-((4,6-diMethoxypyriMidin-2-yl)carbaMoyl)sulfaMoyl)-5-forMaMido-N,N-diMethylbenzaMide 2-{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}-4-(formylamino)-N,N-dimethylbenzamide Foramsulfuron,2-[3-(4,6-Dimethoxy-2-pyrimidinyl)ureidosulfonyl]-4-(formamido)-N,N-dimethylbenzamide |
| CAS | 173159-57-4 |
| EINECS | 605-666-1 |
| InChI | InChI=1/C17H20N6O7S/c1-23(2)15(25)11-6-5-10(18-9-24)7-12(11)31(27,28)22-17(26)21-16-19-13(29-3)8-14(20-16)30-4/h5-9H,1-4H3,(H,18,24)(H2,19,20,21,22,26) |
173159-57-4 - Physico-chemical Properties
| Molecular Formula | C17H20N6O7S |
| Molar Mass | 452.44 |
| Density | 1.471±0.06 g/cm3(Predicted) |
| Melting Point | 199.5° |
| Water Solubility | Solubility in water (g/l at 20 °C) 0.037 (pH 5) 3.293 (pH 7) 94.577 (pH 8) |
| Solubility | Solubility in organic solvents (g/l at 20 °C) Acetone 1.925 Acetonitrile 1.111 1,2-Dichloroethane 0.185 Ethyl acetate 0.362 n-Heptane <0.010 Methanol 1.660 p-Xylene <0.010 |
| Vapor Presure | 4.2 × 10-11 1.3 × 10-10a (Pa at 20 °C) |
| Appearance | neat |
| Color | White |
| pKa | Dissociation constant (pKa at 21.5 °C) 4.6 |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.613 |
| Physical and Chemical Properties | The original drug is light gray-brown solid, melting point 199.5 ℃. The vapor pressure was 1.3 x 10-7m Pa(25 °c). Water solubility (g/L,20 ℃):0.0372(pH = 5), 3.293(pH = 7), 94.577 (pH = 9), solubility in other solvents (g/L,20 °c): methanol 1.660, ethyl acetate 0.362, acetone 1.925. Photolysis stability DT50(20 °c):10.3d(pH = 5),306d(pH = 9). |
173159-57-4 - Risk and Safety
| UN IDs | UN3077(solid) |
| WGK Germany | 1 |
| HS Code | 29242990 |
| Toxicity | LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Collins) |
173159-57-4 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | formamide sulfuron is a sulfonylurea herbicide developed by Bayer Crop Science Company (formerly Avent Company) in Germany. It is mainly used to control annual gramineous weeds and some broadleaf weeds in corn fields. Like other sulfonylurea herbicides, formamide sulfuron is an acetolactate synthase (ALS) inhibitor, which can be absorbed by weed roots and leaves, and is rapidly conducted in the plant, hindering valine, isoleucine, Leucine synthesis, inhibit cell division and growth, sensitive weed roots and leaves absorb the agent, conduct in the plant body, young buds and roots quickly stop growing, young tissues turn yellow, and then die. Formamide sulfuron first entered Romania and Turkey in 2001, and was approved for use in the United States and Europe in 2002. It is mainly mixed with iodosulfuron or mixed with the safety agent diphenoxazole acid. In 2003, it entered the herbicide markets in France, Canada and other countries. It was approved to be used alone or mixed with sulfoketone for pond weeding. In 2003, sales reached 7 million US dollars. It has now been registered in many countries including the United States, Australia, China, etc., and is mainly used to control lawn weeds and weed in corn fields in the United States. |
| Synthesis | N, N-dimethyl-2-aminosulfonyl-4-formylaminobenzamide and 4, 6-dimethoxy-2-((Phenoxycarbonyl) amino)-pyrimidine was prepared by transesterification reaction to obtain formamide sulfuron. The reaction formula is as follows: |
| Mechanism of action and selectivity | Formamide sulfuron is an inhibitor of acetolactate synthase (ALS). Formamide sulfuron is absorbed by weed roots and leaves, and conducts rapidly in the plant, hindering the synthesis of valine, isoleucine, and leucine, inhibiting cell division and growth, and sensitive weed roots and leaves absorb the agent. Conduction in the plant body, the young buds and roots quickly stop growing, the young tissues turn yellow, and then die. The selective basis of formamide sulfuron is that its detoxification metabolism in corn plants is very fast (with or without iodosulfuron), and there is almost no degradation of parent compounds in sensitive plants. There are three main metabolic pathways in maize: hydrolysis of sulfonylurea bridge, aminodeacylation, and oxidative metabolism of dimethoxypyrimidine ring. |
| control object | formamide sulfuron has excellent activity against many annual or perennial gramineous weeds and broadleaf weeds. Gramineae weeds such as barnyard grass, thousand gold, horse Tang, wild oats, brome, false sorghum, bluegrass, ryegrass, crickets, Setaria, etc, broad-leaved weeds such as Xanthium, Abutilon, Solanum nigrum, Pigma, Portulaca, Amaranth, Amaranth, Earanth, Sonchus, Duck Toe grass, Humulus, Chenopodium, Polygonum sorrel, Polygonum Willow, Polygonum curl, Polygonum curl, Polygonum sylvestris, Polygonum sylvestris, Dandelion, Blue Curb, Shepherd's purse, Mandala, Milularia, Polygon. |
| toxicity and environmental biosafety evaluation | in all acute toxicology tests, formamide sulfuron showed low toxicity to mammals. Acute oral LD50 in rats is greater than 5000mg/kg, and acute percutaneous LD50 in rats is greater than 2000mg/kg. No irritation to rabbit skin, moderate irritation to eyes (subsided after 1d). No sensitization to guinea pig skin. No mutagenicity was found in vitro or in vivo. Foramide sulfuron is non-toxic to fish and aquatic invertebrates when LC50 or EC50 values are greater than l00mg/L, and sensitive to green algae and higher aquatic plants, with EC50 values of 12.5mg/L and 0.65 μg/L respectively. No adverse effects were found on birds (wild ducks, crane quails), bees or earthworms. There is no foreseeable risk to the environment for the use of formamide sulfuron at the recommended dosage according to the Good Agricultural Practice (GAP). (2015-11-02) |
| application | suitable crops and safety: cereals such as corn (summer corn, spring corn), etc.; When used twice higher than the recommended dose, some corn varieties will experience short-term whitening or squatting seedlings, but they will return to normal growth soon (2-3 weeks) and have no effect on yield and quality. It is safe for subsequent crops such as wheat, barley, oats, cotton, soybeans, peas, rape, sugar beets, potatoes, etc. |
| usage | treatment of stems and leaves after seedling is effective for weeds from emergence to 7-10 leaf stage. the best application period is weeds from emergence to 4-6 leaf stage. the dosage of formamide sulfuron single dose is usually 30-60g a. I./hm2. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:21:28
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