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1.
Masatoshi Tamaru Naoshi Masuyama Masahiro Sato Fumiaki Takabe Jun Inoue Ryo Hanai 《Pest management science》1997,49(1):76-84
The previously evaluated prototype, methyl 6-acetyl-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, was modified by the introduction of an oximino group. Further extensive synthetic modifications were then made to the 6-alkyl moiety (R1), the ester moiety (R2), the alkoxyimino moiety (R3), the bridge-atom (X) and the 4,6-disubstituted-pyrimidine moiety (A, B, Z). Structure–activity relationships of the synthesized compounds were studied by examining their herbicidal activity against Barnyard grass (Echinochloa oryzicola) in paddy rice at various growth stages, including pre-emergence. The novel herbicide methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate, (KIH-6127) was found to be the most effective compound. The commercial development of this compound is currently in progress. © 1997 SCI. 相似文献
2.
A novel synthesis of methyl 6-acetylsalicylate as a key synthetic intermediate for methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate (KIH-6127) was studied, and directed at 6-substituted pyrimidin-2-yl salicylate herbicides and their analogues. Three synthetic approaches were successful: a modification of the Sandmeyer reaction of 6-acetylanthranilate (Method A), a direct ring-opening reaction of 3-methylphthalide using potassium permangamate and magnesium nitrate (Method B), and a regioselective ortho-lithiation of the protected 3-hydroxyacetophenone (Method C). These methods were applicable for the synthesis of various 6-acyl salicylates. 相似文献
3.
The synthesis of 1-(4,6-dimethoxypyrimidine-2-yl)-7-trifluoromethyl-1,2,3,4-tetrahydropyrido [2,3-d]pyrimidin-2,4-dione has been carried out in such a way that the dimethoxypyrimidine substituent was unambiguously in position 1 of the pyrido[2,3-d]pyrimidine ring. This regioisomer was obtained by cyclization with phosgene of 2-(4,6-dimethoxypyrimidin-2-ylamino)-6-trifluoromethylnicotinamide which had previously been ionized with sodium hydride. It was shown to be identical to the metabolite generated in the soil of winter wheat crops treated previously with the sulfonylurea herbicide flupyrsulfuronmethyl [(methyl 2-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-6-trifluoromethylnicotinate]. The position of the dimethoxypyrimidine substituent had not previously been assigned unambiguously to positions 1 or 3 of the pyrido[2,3-d]pyrimidine ring. The regioisomer was also identical to the cyclization compound generated chemically from flupyrsulfuron in a sterile water buffer at pH 9. The metabolism pathways of flupyrsulfuron in soil are discussed in the light these structure determinations and compared with the soil metabolism pathways frequently observed with other sulfonylurea herbicides. 相似文献
4.
LGC-42153, 2-fluoro-1-[3-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)pyridin-2-yl]propyl methoxyacetate, is a new sulfonylurea herbicide for use in rice. Its breakdown and metabolism were studied in soil under flooded condition using radioactive tracers labelled at either the propyl group or the pyrimidine ring. The half-life of LGC-42153 was approximately 3.0 days. The mass balance over 120 days ranged from 94.0 to 104.2% of applied radiocarbon, and no significant amount of volatiles or [14C]carbon dioxide were observed. Solvent non-extractable radiocarbon reached 11 approximately 14% of applied radiocarbon at 120 days after treatment. The major metabolic reaction was the cleavage of the carboxyl ester bond to give 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(1-hydroxy-2-fluoropropyl)pyridine-3-sulfonyl]urea, which underwent hydrolysis of the sulfonylurea bridge giving 2-(1-hydroxy-2-fluoro)propyl-3-pyridinesulfonamide and 4,6-dimethoxy-2-aminopyrimidine. 相似文献
5.
LGC-42153, 2-fluoro-1-[3-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)pyridin-2-yl] propyl methoxyacetate, is a new sulfonylurea herbicide for use in rice. Its breakdown and metabolism was studied in soil under flooded conditions using two radioactive tracer compounds labelled at either the propyl group or the pyrimidine ring. The half-life of LGC-42153 was approximately 3.0 days. The mass balance over 120 days ranged from 94.0 to 104.2% of applied radiocarbon, and no significant amount of volatiles or [14C]carbon dioxide were observed. Solvent non-extractable radiocarbon reached about 11-14% of applied radiocarbon at 120 days after treatment. The major metabolic reaction was the cleavage of the carboxyl ester bond to give 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(1-hydroxy-2-fluoropropyl)pyridine-3-sulfonyl]urea, which underwent hydrolysis of the sulfonylurea bridge giving 2-(1-hydroxy-2-fluoro)propyl-3-pyridinesulfonamide and 4,6-dimethoxy-2-aminopyrimidine. 相似文献
6.
设计合成了一系列结构新颖的嘧啶联吡唑甲酰胺类化合物5a~5o,其结构均经过1H NM R和MS分析确证。初步生物活性测试结果表明:在有效成分150 g/hm2剂量下苗后茎叶喷雾处理时,化合物(R)-N-[1-(4-氯苯基)乙基]-3-二氟甲基-1-(4,6-二甲氧基嘧啶-2-基)-1H-吡唑-4-甲酰胺(5c)、N-[1-(4-氯苯基)乙基]-1-(4,6-二甲氧基嘧啶-2-基)-N-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺(5i)和N-[1-(4-氯苯基)乙基]-1-(4,6-二甲氧基嘧啶-2-基)-3-三氟甲基-1H-吡唑-4-甲酰胺(5k)对繁缕Stellaria media的抑制率高达90%以上;而同样剂量下苗前土壤喷雾处理时,化合物N-[1-(4-氯苯基)乙基]-3-二氟甲基-1-(4,6-二甲氧基嘧啶-2-基)-1H-吡唑-4-甲酰胺(5b)和5c对繁缕的抑制率达100%。该类结构化合物有望作为除草先导化合物进行开发。 相似文献
7.
Three field trials were conducted from 2003–2004 at Utsunomiya University, Japan, to evaluate the safety and herbicidal activity of pyribenzoxim (benzophenone O -[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxybenzoyl]oxime) in turfgrass. Pyribenzoxim showed a high level of safety in bentgrass ( Agrostis palustris Huds.) and zoysiagrass ( Zoysia matrella ) ≤ 300 g ai ha−1 and it controlled various major grass weeds, including annual bluegrass ( Poa annua L.), large crabgrass ( Digitaria sanguinalis L.), and green foxtail ( Setaria viridis L.), and broadleaf weeds, including common dandelion ( Taraxacum officinale Weber), horseweed ( Erigeron canadensis L.), shepherd's-purse ( Capsella bursa-pastoris (L.) Medic.), common chickweed ( Stellaria media L.), common lambsquarters ( Chenopodium album L.), creeping woodsorrel ( Oxalis corniculata L.), and common dayflower ( Commelina communis L.) by fall or spring application. In comparison with bispyribac-sodium (sodium 2,6-[bis(4,6-dimethoxy-2-pyrimidin-2-yl)oxy]benzoate), pyribenzoxim showed a higher safety level in bentgrass and a stronger herbicidal activity on grass weeds; in particular, annual bluegrass and large crabgrass. 相似文献
8.
以4,6-二氯-5-硝基嘧啶为起始原料,经过还原胺化、取代、醚化等一系列反应,得到11个未见文献报道的嘌呤氧基苯氧丙酸酯类化合物1a~1k,其结构经1H NM R和M S确认。初步生物活性测定表明:在200 mg/L下,所有目标化合物均表现出一定的除草活性,其中化合物1f((R)-2-(4-((9-(4-氯苯)-8-(三氟甲基-9H-嘌呤-6-基)氧)苯氧)丙酸丁酯)和1h((R)-2-(4-((9-(4-氯苯)-8-(三氟甲基-9H-嘌呤-6-基)氧)苯氧)丙酸乙酯)对靶标的抑制率几乎都达到100%。 相似文献
9.
ALBERT J. FISCHER DAVID P. CHEETHAM FRANCESCO VIDOTTO RAFAEL DE PRADO 《Weed Biology and Management》2004,4(4):206-212
Bispyribac-sodium {sodium 2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy] benzoate} has recently been introduced to California where it effectively controls Echinochloa spp. in rice ( Oryza sativa L.). However, biotypes of early watergrass ( Echinochloa oryzoides (Ard.) Fritsch) and late watergrass ( E. phyllopogon (Stapf ) Koss.) have evolved resistance to this herbicide. In 2001 and 2002, greenhouse and field experiments evaluated interactions between thiobencarb { S -[(4-chlorophenyl) methyl] diethylcarbamothioate} and bispyribac-sodium on resistant (R) and susceptible (S) late watergrass in California rice. Synergism was assessed using Colby's test and regression analysis. In the greenhouse, thiobencarb at 4480 and 5333 g ai ha−1 synergistically reduced bispyribac-sodium GR50 values on the R and S biotypes by 50–70% without increasing toxicity to rice. Synergism was also observed on S late watergrass in the field when 10 g ai ha−1 bispyribac-sodium was mixed with 1120–2240 g ai ha−1 thiobencarb. These effects could be related to interactions between thiocarbamates and enzymes in Phase I reactions of herbicide metabolism. This synergism results in better control at lower rates allowing a reduction in weed control costs, the herbicide load on the environment and a lower selection pressure towards resistant weed biotypes. 相似文献
10.
为明确蜡状芽孢杆菌对烟嘧磺隆的降解及母体和降解产物对环境生物的毒性,采用超高效液相色谱-质谱 (UPLC-TQD) 联用法分析了蜡状芽孢杆菌对烟嘧磺隆的降解产物,同时参照“化学农药环境安全评价试验准则”方法,分别测定了烟嘧磺隆和主要降解产物2-氨基-4,6-二甲氧基嘧啶对斑马鱼、大型溞和斜生栅列藻3种水生生物的急性毒性。结果表明:经蜡状芽孢杆菌降解后,共检测到4种烟嘧磺隆的降解产物,分别为2-氨基-4,6-二甲氧基嘧啶 ( Ⅰ )、2-[N-(氨基甲基) 氨磺酰基]-N,N-二甲基烟酰胺 ( Ⅱ )、2-[1-(4,6-二甲氧基嘧啶-2-基) 脲基]-N,N-二甲基烟酰胺 ( Ⅲ ) 和N-(4,6-二甲氧基嘧啶-2-氨基甲酰基)-1-(甲基亚氨基) 甲磺酰胺 ( Ⅳ ),其中2-氨基-4,6-二甲氧基嘧啶 ( Ⅰ ) 为主要降解产物,由此推测蜡状芽孢杆菌对烟嘧磺隆的降解主要是通过使其磺酰脲桥上C—N键、C—S键以及吡啶环断裂而实现的。毒性测定结果显示:烟嘧磺隆及主要降解产物 Ⅰ 对斑马鱼的96 h-LC50值分别为16.95和 > 100.0 mg/L,其急性毒性等级均为“低毒”;两者对斜生栅列藻的72 h-ErC50值分别为8.070和142.7 mg/L,均为“低毒”;对大型溞的48 h-EC50值分别为9.190和51.95 mg/L,分别为“中毒”和“低毒”。研究表明,烟嘧磺隆经蜡状芽孢杆菌降解后,其主要降解产物对3种水生生物的毒性均明显降低。 相似文献
11.
以2,5-二羟基苯甲酸甲酯和三氟羧草醚为起始原料,设计合成了3个系列20个新的三氟羧草醚类似物,通过核磁共振氢谱、碳谱对其结构进行了表征。分别采用小杯法和室内盆栽法测定了目标化合物的除草活性。结果表明,化合物 III-02 [5-(2-氯-4-三氟甲基苯氧基)-2-硝基苯甲酸-(6-甲基苯并噻唑-2-基)酯]对单子叶杂草的除草活性明显高于对照药剂三氟羧草醚,其对稗草Echinochloa crusgalli和马唐Digitaria sanguinalis根茎生长的EC50值分别为2.03、0.93 μg/mL和1.49、0.52 μg/mL;在有效成分100 g/hm2的施药剂量下,化合物 III-02 对单子叶杂草稗草、马唐及狗尾草Setaria viridis的防治效果均在85%以上,明显高于三氟羧草醚,对阔叶杂草马齿苋Portulaca oleracea、反枝苋Amaranthus retroflexus及苘麻Abutilon theophrasti的防治效果可达100%。初步构效关系表明,2-硝基苯甲酰衍生物的除草活性明显优于其2-甲氧基衍生物,三氟羧草醚苯甲酸酯衍生物对单子叶杂草的除草活性明显高于其苯甲酰胺衍生物。 相似文献
12.
为研究棉田除草剂溴嘧氯草醚(开发代号SIOC0426,化学名称为N-[2-氯-6-(4,6-二甲氧基-2-嘧啶氧基)苄基]-4-溴苯胺)的中试合成工艺,以2-氟-6-氯苯甲醛为起始原料,通过水解、缩合、还原和亲核取代反应在公斤级规模上合成了溴嘧氯草醚,用高效液相色谱外标法测定了原药含量,通过三维高效液相色谱-质谱联用(HPLC-DAD-MS)技术对原药中的杂质结构进行了鉴定。结果表明,反应总收率高于80%,原药含量大于98%,主要杂质为未反应完全的中间体2-[(4-溴苯氨基)甲基]-3-氯苯酚和溴嘧氯草醚Smiles重排产物。该工艺反应条件温和,反应收率高,原药含量高,"三废"排放较少,较适合工业化放大生产。 相似文献
13.
Yukio Nezu Nobuhide Wada Fumitaka Yoshida Takeshige Miyazawa Tsutomu Shimizu Toshio Fujita 《Pest management science》1998,52(4):343-353
The activity of a number of O-(4,6-dimethoxypyrimidin-2-yl)salicylic acids and their thio analogs inhibiting acetolactate synthase (ALS) preparation was measured. The effects of substituents on the salicylic-benzene ring on the inhibitory activity were analyzed quantitatively with physicochemical substituent parameters. For 6-substituted (thio)salicylic acids, the activity was shown to vary parabolically with the ‘intramolecular’ steric parameter ( Es ). In addition, the higher steric dimension of substituents in terms of the STERIMOL width or length parameter lowered the activity. The field-inductive electron-withdrawing property of the 6-substituents in terms of the Swain–Lupton–Hansch F was favorable for the activity of salicylic acid series. In 5-substituted salicylic acids, the activity was increased by electron-donating substituents with smaller size. The relationships between ALS inhibitory and herbicidal activities were also analyzed with some weed species. Both pre- and post-emergence activities against barnyard grass, Echinochloa crus-galli, were linearly related to the ALS inhibitory activity after allowing for the hydrophobic factor that may contribute to the transport processes. Those against two broad-leaved weed species, Polygonum convolvulus and Abutilon theophrasti were linearly related to the in-vitro activity with no significant participation of the hydrophobic factor. © 1998 SCI 相似文献
14.
Yukio Nezu Masahiro Miyazaki Kazuhiko Sugiyama Nobuhide Wada Ikuo Kajiwara Takeshige Miyazawa 《Pest management science》1996,47(2):115-124
A new series of the O-pyrimidinylsalicylates was synthesized and their herbicidal activity was examined. Some of these compounds showed very strong herbicidal activity under pre- and post-emergent treatment conditions against various kinds of grass and broadleaf weeds. Among these compounds, O-(4, 6-dimethoxypyrimidin-2-yl) salicylic acid and its methyl ester were found to exhibit the highest activity. The herbicidal symptoms observed after the treatments included early cessation of plant growth followed by chlorosis, necrosis and plant death. The symptoms were similar to those caused by sulfonylureas and imidazolinones, which inhibit branched-chain amino acid biosynthesis. 相似文献
15.
为了探索天然产物Cedarmycins衍生物的结构与活性关系,以α-亚甲基-β-羟甲基-γ-丁内酯为起始原料,经过与不同取代的羧酸缩合,合成了19个新的(4-亚甲基-5-羰基-3-四氢呋喃基)-苯甲酸甲酯衍生物。杀菌活性测定结果表明,该类衍生物具有广谱的杀菌活性,尤其对水稻纹枯病菌Rhizoctonia solani和辣椒疫霉Phytophthora capsici显示出很强的杀菌活性,其中化合物2e(R=2,4-2Cl)对这2种病菌的EC50值约为1.6 mg/L。 相似文献
16.
Fungicides containing the imidazole and triazole groups are known to block the 14α-demethylation reaction in ergosterol biosynthesis, which is a cytochrome P-450 enzyme system. Fungicides related to diclobutrazol [(2RS, 3RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol] bind to cytochrome P-450 in rat liver microsomes, whole yeast cells, yeast microsomes and to a partially purified cytochrome P-450 from yeast, with Type II spectral changes. The most fungicidally active isomer (2R, 3R) shows greater binding than the less active (2S, 3S)-enantiomer to yeast microsomes; when the cytochrome P-450 was purified, a preparation was obtained to which binding more closely matched the fungicidal activity. Binding to rat liver microsomes does not reflect the fungicidal activity of the compounds. 相似文献
17.
Anil K. Sen Gupta Tapas Bhattacharya Kanchan Hajela Kripa Shankar Shakeel Ahmad 《Pest management science》1985,16(1):65-72
A series of 5,6-diphenyl-3-substituted-thio-1,2,4-triazines ( II-V ) was prepared by treating 5,6-diphenyl-1,2,4-triazine-3-thiol ( I ) with corresponding electrophiles. Condensation of IV or V with 1,2-phenylenediamines gave 2-[(5,6-diphenyl-1,2,4-triazin-3-yl) thiomethyl-1H-benzimidazoles] ( VI ). IV was converted into its corresponding hydrazide ( VII ) by the action of hydrazine hydrate. N-Benzylidene derivatives ( VIII ) were prepared by the condensation of VII with appropriate aryl or heterocyclic aldehydes. The pesticidal activities of all the compounds thus synthesised were determined. 相似文献
18.
Laura Scrano Sabino A Bufo Piero Perucci Pierre Meallier Mohammed Mansour 《Pest management science》1999,55(9):955-961
The degradation in the liquid phase of rimsulfuron and its commercial 250 g kg−1 WG formulation (Titus®) was investigated. Photolysis reactions were carried out at 25 °C by a high-pressure mercury arc (Hg-UV) and a solar simulator (Suntest), while the hydrolysis rate was determined by keeping aqueous buffered samples in the dark. The effects of solvent and water pH on reaction kinetics were studied, and the results compared to literature data. Photoreactions of the commercial product in organic solvents were faster than pure rimsulfuron. Under simulated sunlight in water, the half-life for the photolysis reaction ranged from one to nine days at pH 5 and 9, respectively. The hydrolysis rate was as high as the photolysis rate, but decreased on increasing water pH. The main metabolite identified in neutral and alkaline conditions as well as in acetonitrile was N-[(3-ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2-pyridinamine, while N-(4,6-dimethoxy-2-pyrimidinyl)-N-[(3-(ethylsulfonyl)-2-pyridinyl)]urea and minor metabolites prevailed in acidic conditions. © 1999 Society of Chemical Industry 相似文献
19.
A series of 2-amino-5-substituted pyridine derivatives was synthesized and their molluscicidal activity against white garden, Theba pisana (Müller), and brown garden, Helix aspersa (Müller), snails was investigated by two methods of application. Some of these compounds showed strong activity under laboratory conditions against the two types of snail. T pisana was more sensitive to the tested compounds than H aspersa. The most effective compounds were 2-amino-5-(benzotriazole-1-ylmethyl)-3-methylpyridine, 2-amino-5-[1-(benzotriazole-1-yl)nonyl]-3-methylpyridine and 2-[(1,2,4-triazole-1-ylmethyl)amino]-3-methylpyridine which exhibited high molluscicidal activity. The toxicity results are discussed in relation to the chemical structures. © 1999 Society of Chemical Industry 相似文献
20.
BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses. RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 microg mg(-1) insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated. CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. 相似文献