CN101230042A - Uracil weeding compounds introducing amide structure - Google Patents

Uracil weeding compounds introducing amide structure Download PDF

Info

Publication number
CN101230042A
CN101230042A CNA200810030588XA CN200810030588A CN101230042A CN 101230042 A CN101230042 A CN 101230042A CN A200810030588X A CNA200810030588X A CN A200810030588XA CN 200810030588 A CN200810030588 A CN 200810030588A CN 101230042 A CN101230042 A CN 101230042A
Authority
CN
China
Prior art keywords
phenyl
trifluoromethyl
methyl
dihydro
chloro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CNA200810030588XA
Other languages
Chinese (zh)
Inventor
黄明智
任叶果
黄路
雷满香
胡礼
柳爱平
欧晓明
项军
王晓光
刘兴平
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan Research Institute of Chemical Industry
Original Assignee
Hunan Research Institute of Chemical Industry
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hunan Research Institute of Chemical Industry filed Critical Hunan Research Institute of Chemical Industry
Priority to CNA200810030588XA priority Critical patent/CN101230042A/en
Publication of CN101230042A publication Critical patent/CN101230042A/en
Pending legal-status Critical Current

Links

Landscapes

  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention discloses a uracil herbicidal compound introducing amide structure shown by the general formula (I). X are hydrogen, fluorin, and chlorine; Y are hydrogen, fluorin, and chlorine; R<1> is hydrogen, C1-C4 alkyl, C1-C4 halogenated alkyl; R<2> is hydrogen, C1-C4 alkyl, C1-C4 halogenated alkyl; Q is C1-C4 halogenated alkyl, phenyl, substituted phenyl, C1-C4 dilute oxyl, C1-C4 alkyne, C1-C4 alkyl, alkoxy, C1-C4 alkylthio, C1-C4 alkoxycarbonyl, halogen, nitryl, substituted phenoxy, substituted pyridyloxy, Alpha- naphthyloxy. The compound of the general formula (I) exhibits better herbicidal activity against broadleaf weeds such as abutilon, pigweed, and emarginate amaranth and has a control efficiency of more than 80 percent at the dosage of 75g ai/ha in soil treatment before seedling or stem treatment after seedling; the product can also prevent monocotyledonous weeds such as crabgrass, barnyard grass, green bristlegrass, etc.

Description

Introduce the uracil weeding compounds of amide structure
Technical field
The present invention relates to uracil weeding compounds of introducing amide structure and preparation method thereof.
Background technology
Bibliographical information uracil proporphyrinogen oxidase inhibitor has weeding activity efficiently, existing many abroad patent reports.The exploitation of this class weedicide starts from the sixties in 20th century the earliest, and Du-pont company had developed a series of new variety in this field at that time, for example bromacil (bromacil, 1) is exploitation in 1962 with isoprocil (isocil, 2), terbacil (terbacil, 3) etc. is exploitation in 1966.1986, EP 0195346 report DCMD (4) introduced trifluoromethyl in the 6-position of uracil, has introduced a multiple functionalized phenyl in the 3-position.Trifluoromethyl is a very important substituting group, its introducing is greatly favourable to improving activity, on the 6-position of reporting respectively as US 4927451, EP 473551, JP 03215476, EP 3712782 be methyl, phenyl or and the compound 5 when encircling, 6,7,8 activity is poor than the trifluoromethyl analogue all.And the structural modification of 6-trifluoromethyl uracil is lasted till now always.Wherein the UCC C-4243 (9) of US4943309 report developed into that wheatland uses to the effective weedicide of annual grassy weeds.2000, butafenacil (10) list marketing of Syngenta company exploitation, it is mainly used in anti-Gramineae and broadleaf weeds in the perennial crop, also can use as defoliating agent in the cotton field.Above-mentioned 1-11 structural formula of compound is as follows:
In the last few years, each big agricultural chemicals company was characterized in all in the uracil weeding agent of ceaselessly developing with general structure (11) expression that the 1-position was methyl or amino in the world, and the 6-position is a trifluoromethyl, and the 3-position is multiple functionalized phenyl ring or heterocycle and fused heterocycle.It is fluorine that the replacement of phenyl ring is characterized as the 2-position, and the 4-position is chlorine or cyano group, and the 5-position mostly is a long-chain substituting group, having summed up the 5-bit substituent as WO 0139597 is nitro, cyano group, alkyl, carboxyl, thiocarbamate (or ester), hydroxyl, (thiohydroxy) that contains sulfydryl, amino, hydroxylamino, sulfoamido, halogen, C 1-C 4Alkoxyl group, C 1-C 4Alkyl carbonyl, C 1-C 4Carbalkoxy, C 2-C 4Alkenyloxycarbonyl, C 2-C 4Alkynes oxygen carbonyl, C 1-C 4The alkanamine carbonyl, two-(C 1-C 4-alkyl)-amino-carbonyl, carbobenzoxy, the substituted aniline carbonyl, alkylsulfonamido, phenoxy group, naphthyloxy, N-benzoyl group-N-alkyl sulphonyl, N-pyridine acyl-N-alkyl sulphonyl, N-furans acyl group-N-alkyl sulphonyl, N-pyridine acyl-N-alkyl sulphonyl, N-thiophene acyl group-N-alkyl sulphonyl etc.; WO 02098227 patent report 5-position is for replacing fragrant oxygen, substituted pyridines oxygen base; UP 6245715 patent report 5-positions are the imines alkoxyl group; UP 6391826 patent report 5-positions are the Alpha-hydroxy acid esters with chirality; The 5-position of UP 6403534 patent reports is the acyl alkoxyl group; UP6451740, UP6667413, UP7205260 patent report 5-position are for replacing fragrant oxygen, substituted aromatic amines substituted benzyl; UP6664214 patent report 5-position is a substituted benzyloxy; UP6689773, UP6849618 patent report 5-position are the sulfonylurea acyl group." the N-substituted phenyl urea pyrimidines of weeding " patent of invention (application number 200610032425 that Hunan Chemical Research Institute was applied for as first contriver by the inventor on October 19th, 2006.6), related to the uracil compound of introducing amide structure.
For reaching weeding activity and the security purpose that strengthens the uracil compound of introducing amide structure, the inventor constantly is optimized transformation to above-claimed cpd, especially structure 11 compounds is optimized transformation.
Summary of the invention
The purpose of this invention is to provide with uracil weeding compounds of introducing amide structure on the 5-position of chemical structure of general formula (I) expression and preparation method thereof.
(I) is as follows for chemical structure of general formula:
Figure S200810030588XD00021
X is a hydrogen, fluorine, chlorine;
Y is a hydrogen, fluorine, chlorine;
R 1Be hydrogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
R 2Be hydrogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
Q is C 1-C 4Haloalkyl, phenyl, substituted-phenyl, C 1-C 4Alkene oxygen base, C 1-C 4Alkynyloxy group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio, C 1-C 4The phenoxy group that carbalkoxy, halogen, nitro, phenyl replace, substituted pyridines oxygen base, alpha-naphthoxy base.
The preparation method of formula of of the present invention (I) compound is as follows:
Add a certain amount of raw material A and triethylamine in organic solvent, the frozen water cooling drips the acyl chlorides B of respective amount down, dropwises to react at a certain temperature to obtain target compound in 1-12 hour.Preferred organic solvents is an ethylene dichloride; Mol ratio is A: acyl chlorides B: triethylamine=1: 1～1.2: 1.1～1.3; Temperature of reaction is that room temperature is to the solvent refluxing temperature; Reaction times is 2～6 hours.
Raw material A can adopt US 4859229, and the method that US 6403534 describes is synthetic to be obtained.Raw material acyl chlorides B directly buys or reference literature synthesizes.
Physico-chemical property with present method synthetic part general formula (I) compound sees Table 1.
Table 1: the chemical structure and the fusing point of the The compounds of this invention of part shown in general formula (I)
Figure S200810030588XD00032
Compound Y X R 1R 2Q m.p (℃)
I-01 Cl H CH 3 CH 3 CH 2Cl 152.0-153.8
I-02 Cl H H H CH 2Cl 251.3-252.0
I-03 Cl H H H C 6H 5 161.2-163.5
I-04 Cl H H H C 6H 4(2-CH 3) 167.9-168.1
I-05 Cl F CH 3 CH 3 CH 2Cl 267.5-269.0
I-06 Cl H H H C 6H 4(4-OCH 3) 177.1-179.2
I-07 Cl H H H OC 6H 4(2-F) 177.6～178.3
I-08 Cl F H H OC 6H 4(4-COOCH 3) 166.2～167.6
I-09 Cl F H CH 3OC 6H 4(3-F) faint yellow viscous fluid
I-10 Cl H H CH 3 OC 6H 4(3-F) 176.3～177.2
I-11 Cl F H CH 3OC 6H 4(2-CH 3) faint yellow viscous fluid
I-12 Cl H H CH 3OC 6H 4(3-CH 3-4-Cl) faint yellow viscous fluid
I-13 Cl H H CH 3 OC 6H 4(3-F) ＞250
I-14 Cl F H CH 3OC 6H 4(3-CH 3) faint yellow viscous fluid
I-15 Cl F H CH 3OC 6H 4(3,5-2CH 3) faint yellow viscous fluid
I-16 Cl F H CH 3 OC 6H 4(3-Cl) 168.4～169.9
I-17 Cl F H CH 3OC 6H 4(3-CH 3-4-Cl) faint yellow viscous fluid
I-18 Cl F H CH 3OC 6H 4(4-CH 3) faint yellow viscous fluid
I-19 Cl H H CH 3 OC 6H 4(4-C(CH 3) 3) 108.8-110.7
I-20 Cl Cl H CH 3 OC 6H 4(4-C(CH 3) 3) 147.4-148.7
I-21 Cl H H CH 3 OC 6H 4(2，4-2Cl) 202.7-203.7
I-22 Cl Cl H CH 3 OC 6H 4(2，4-2Cl) 202.0-202.9
I-23 F H H CH 3 OC 6H 4(3-F) 105.5-106.2
I-24 F H H CH 3 OC 6H 4(3-CH 3) 115.8-116.5
I-25 F H H CH 3 OC 6H 4(4-CH 3) 131.5-132.3
I-26 F H H H OC 6H 4(4-NO 2) 199.3-199.8
I-27 F H H CH 3 OC 6H 4(2-OCH 3) 66.5-67.0
I-28 F H H CH 3 OC 6H 4(2，4-2Cl) 185.1-186.3
I-29 F H H CH 3 OC 6H 4(2-F，4-NO 2) 166.8-167.1
I-30 F H H CH 3 OC 6H 4(4-Ph) 97.4-98.4
I-31 F H H CH 3 OC 6H 4(2，4-2Cl) 292.8-293.5
I-32 Cl Cl H CH 3 OC 6H 4(3-F) 56.6-58.1
I-33 Cl Cl H CH 3 OC 6H 4(2-NO 2，4-F) 121-122.5
I-34 Cl Cl H CH 3 OC 6H 4(2，4-2Cl) 67.8-69.5
I-35 Cl Cl H CH 3 199.2-200.7
I-36 F H H CH 3
Figure S200810030588XD00042
112.8-113.4
I-37 Cl Cl H CH 3 OC 6H 4(3-CH3) 60.2-62.5
I-38 Cl Cl H CH 3 OC 6H 4(3-OCH3) 54.5-55.8
I-39 Cl Cl H H OC 6H 4(3，5-2CH 3) 162.6-163.8
I-40 Cl Cl H CH 3 OC 6H 4(4-Ph) 100.3-100.9
I-41 Cl Cl H H OC 6H 4(2-NO 2，5-F) 245.1-245.5
I-42 Cl Cl H H OC 6H 4(2，4-2Cl) 200.5-201.4
I-43 Cl Cl H H OC 6H 4(4-NO 2) 185.4-186.7
I-44 Cl Cl H CH 3 OC 6H 5 65.8-66.9
I-45 F H H CH 3 OC 6H 5 136.1-136.8
I-46 F H H CH 3 OC 6H 4(3，5-2CF 3) 146.5-147.9
I-47 F H H CH 3 OC 6H 4(3-CH 3，4-Cl) 70.3-71.2
I-48 Cl Cl H CH 3 OC 6H 4(3-CH 3，4-Cl) 52.0-54.0
I-49 Cl Cl H CH 3 OC 6H 4(3，5-2CF 3) 160.5-161.3
I-50 F H H H OCH 2C≡CH 113.5-114.9
I-51 F H H CH 3
Figure S200810030588XD00051
74.2-75.9
I-52 Cl Cl H CH 3
Figure S200810030588XD00052
85.4-86.8
I-53 F H H CH 3 OC 6H 4(4-SCH 3) 38.8-40.9
General formula of the present invention (I) compound has efficient, safe herbicidal effect, uses before seedling or behind the seedling, can effectively control broadleaf weed, and monocotyledon weed is also had certain preventive effect.
Embodiment
Embodiment 1:3-chloro-N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2, the preparation of 2-dimethyl propylene acid amides (Compound I-05).
In the 100mL round-bottomed flask, add 1.35g (4.0mmol) intermediate 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl) pyrimidine-2,4 (1H, 3H)-diketone, 30mL ethylene dichloride and 0.45g (4.4mmol) triethylamine, magnetic agitation, the frozen water cooling down, slowly drip 0.62g (4.0mmol) Chloropivaloyl chloride, dropwise and at room temperature react 2h.Add 100mL water in the reaction solution, tell organic layer, organic layer is water and saturated brine washing successively, anhydrous sodium sulfate drying is through decompression precipitation, silica gel column chromatography, obtain 1.34g faint yellow solid 3-chloro-N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2,2-dimethyl propylene acid amides (mp:267.5-269.0 ℃).Content 95%, yield 70%.
1H NMR(CDCl 3，ppm)δ：1.39(s，6H，2CH 3)，3.55(s，3H，NCH 3)，6.34(s，1H，＝CH)，3.67(s，2H，CH 2)，7.31(d，J＝8.7，1H，ArH)，8.07(s，1H，NH)，8.50(d，J＝7.5Hz，1H，ArH).
Embodiment 2:N-(the preparation of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) propionic acid amide (Compound I-09).
In the 100mL round-bottomed flask, add 1.35g (4.0mmol) intermediate 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl) pyrimidine-2,4 (1H, 3H)-diketone, 30mL ethylene dichloride and 0.45g (4.4mmol) triethylamine, magnetic agitation, the frozen water cooling down, slowly drip fluorobenzene oxygen propionyl chloride between 0.8g (4.0mmol) 2-, dropwise and at room temperature react 2h.Add 100mL water in the reaction solution, tell organic layer, organic layer is water and saturated brine washing successively, anhydrous sodium sulfate drying is through decompression precipitation, silica gel column chromatography, obtain the faint yellow dope of 1.44g, N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) propionic acid amide.Content 93%, yield 67%.
1H NMR(CDCl 3，ppm)δ：1.65～1.68(d，J＝6.9，3H，CHC H 3)，3.55(s，3H，NCH 3)，4.79～4.82(q，J＝6.9，1H，C HCH 3)，6.36(s，1H，＝CH)，6.69～7.32(m，5H，ArH)，8.51～8.54(dd，J＝7.2，2.7Hz，1H，ArH)，8.84～8.85(s，1H，NH).
Embodiment 3:N-(the preparation of 4-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide (Compound I-21).
In the 100mL round-bottomed flask, add 1.28g (4.0mmol) intermediate 3-(5-amino-4-two-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl) pyrimidine-2,4 (1H, 3H)-diketone, 30mL ethylene dichloride and 0.45g (4.4mmol) triethylamine, magnetic agitation, the frozen water cooling down, slowly drip 1.01g (4.0mmol) 2-(2,4-two-chlorobenzene oxygen) propionyl chloride, dropwise and at room temperature react 2h.Add 100mL water in the reaction solution, tell organic layer, organic layer is water and saturated brine washing successively, anhydrous sodium sulfate drying is through decompression precipitation, silica gel column chromatography, obtain 1.64g faint yellow solid N-(4-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide.(mp：202.7-203.7℃)。Content 94%, yield 72%.
1H NMR(CDCl 3，ppm)δ：9.03(s，1H，NH)；8.95(d，J＝7.8Hz，1H ArH)；8.35(s，1H，ArH)；7.26(d，J＝5.7Hz，1H，ArH)；6.96～7.04(m，2H，ArH)；6.36(s，1H，＝CH)；5.07～5.13(q，1H，CH)；3.55(s，3H，NCH 3)1.79(d，J＝6.6Hz，3H，CH-C H 3).
Embodiment 4:N-(2, the preparation of 4-two-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide (Compound I-22).
In the 100mL round-bottomed flask, add 1.41g (4.0mmol) intermediate 3-(5-amino-2,4-two-chloro-phenyl-)-1-methyl-6-(trifluoromethyl) pyrimidine-2,4 (1H, 3H)-diketone, 30mL ethylene dichloride and 0.45g (4.4mmol) triethylamine, magnetic agitation, the frozen water cooling slowly drips 1.01g (4.0mmol) 2-(2 down, 4-two-chlorobenzene oxygen) propionyl chloride dropwises and at room temperature reacts 2h.Add 100mL water in the reaction solution, tell organic layer, organic layer is water and saturated brine washing successively, and anhydrous sodium sulfate drying is through the decompression precipitation, silica gel column chromatography, obtain 1.77g faint yellow solid N-(2,4-two-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide.(mp：202.0-202.9℃)。Content 93%, yield 72%.
1H NMR(CDCl 3，ppm)δ：8.93(s，1H，NH)；8.90(s，1H ArH)；8.36(s，1H，ArH)；7.54(d，J＝5.7Hz，2H，ArH)；6.97～7.04(m，2H，ArH)；6.37(s，1H，＝CH)；5.05～5.12(q，1H，CH)；3.55(s，3H，NCH 3)1.80(d，J＝6.6Hz，3H，CH-C H 3).
The embodiment 5 N-(preparation of 4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide (Compound I-28).
In the 100mL round-bottomed flask, add 1.21g (4.0mmol) intermediate 3-(5-amino-2-fluorophenyl)-1-methyl-6-(trifluoromethyl) pyrimidine-2,4 (1H, 3H)-diketone, 30mL ethylene dichloride and 0.45g (4.4mmol) triethylamine, magnetic agitation, the frozen water cooling down, slowly drip 1.01g (4.0mmol) 2-(2,4-two-chlorobenzene oxygen) propionyl chloride, dropwise and at room temperature react 2h.Add 100mL water in the reaction solution, tell organic layer, organic layer is water and saturated brine washing successively, anhydrous sodium sulfate drying is through decompression precipitation, silica gel column chromatography, obtain 1.62g faint yellow solid N-(4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide.(mp：185.1-186.3℃)。Content 96%, yield 75%.
1H NMR(CDCl 3，ppm)δ：9.01(s，1H，NH)；8.41～8.45(q，1H ArH)；7.46(d，J＝2.4Hz，1H，ArH)；7.25～7.29(m，1H，ArH)；7.24(d，J＝2.7Hz，1H，ArH)；6.86～6.99(m，1H，ArH)；6.87(d，J＝9.0Hz，1H，ArH)；6.36(s，1H，＝CH)；4.63(s，2H，CH 2)；3.54(s，3H，NCH 3).
Application Example 1: potted plant weeding test
Accurately take by weighing sample, after the The suitable solvent dissolving, add small amounts of emulsifiers, adding distil water is settled to 10ml and adopts suitable spraying machine sprinkling again, and reduced unit's area dose is 75gai/ha.At sectional area 64cm 2The plastic tub alms bowl in quantitative dress soil, flatten, water permeable, choose full seed, dicotyledonous select for use lamb's-quarters (Chenopodium album), piemarker (Abutilon theophrasti), recessed amaranth (Amaranthus ascedense) of the same size, unifacial leaf is selected lady's-grass (Digitariasanguinalis), barnyard grass grass (Echinochloa crus-galli), Herba Setariae Viridis (Setaria viridis) for use, divide single, double cotyledon plant to divide the pot culture kind, respectively account for 1/3 of alms bowl area, cover thick fine earth of 1cm and trickle, place hot-house culture.Treat that unifacial leaf examination material grows to 1 heart stage of 1 leaf, dicotyledonous examination material grows to 2 leaf periods, carry out seedling with soup after the cauline leaf spraying handle, soil treatment before the seedling is carried out in the sowing of examination material next day.Put back to the greenhouse subsequently.Range estimation overground part growing state after 15 days, calculate growth inhibition ratio according to following formula:
Growth inhibition ratio (%)=100* (contrast plant height-processing plant height)/contrast plant height
Carry out the weeding activity classification according to growth inhibition ratio:
++，＞80％；+，80～50％；-，＜50％。
Table 2: potted plant weeding test-results
compd Soil treatment (75gai/ha) Cauline leaf is handled (75gai/ha)
Piemarker Lamb's-quarters Recessed amaranth Lady's-grass The barnyard grass grass Herba Setariae Viridis Piemarker Lamb's-quarters Recessed amaranth Lady's-grass The barnyard grass grass Herba Setariae Viridis
I-01 I-02 I-03 I-04 I-05 I-06 I-07 I-08 I-09 I-10 I-11 I-12 I-13 I-14 I-15 I-16 I-17 I-18 I-19 I-20 I-21 I-22 I-23 I-24 ++ - - - ++ - - - + - + - ++ + + - - - - - - - ++ ++ ++ - - - ++ - - + ++ - ++ + + ++ ++ ++ ++ ++ - - - - ++ ++ ++ - - - ++ - - + ++ - ++ - ++ ++ ++ ++ ++ ++ - - - - ++ ++ ++ - - - ++ - - - ++ - - - ++ ++ ++ + + ++ - - - - - - ++ - - - ++ - - - ++ - - - - ++ + + + + - - - - - - ++ - - - ++ - - - ++ - - - + ++ ++ + + + - - - - - - ++ + ++ ++ ++ ++ - - ++ - ++ ++ ++ ++ ++ ++ ++ ++ - - - - ++ ++ ++ + ++ ++ ++ ++ - - ++ - ++ ++ ++ ++ ++ ++ ++ ++ - - - - ++ ++ ++ - - - ++ - - - ++ - ++ ++ ++ ++ ++ ++ ++ ++ - - - - ++ ++ ++ - - - ++ - - - + - + - + ++ ++ + ++ ++ - - - - - - ++ - - - ++ - - - - - + - - ++ + + - + - - - - - - ++ - - - ++ - - - + - + - + ++ ++ + ++ ++ - - - - - -
I-25 I-26 I-27 I-28 I-29 I-30 I-31 I-32 I-33 I-34 I-35 I-36 I-37 I-38 I-39 I-40 I-41 I-42 I-43 I-44 I-45 I-46 I-47 I-48 I-49 I-50 I-51 I-52 I-53 ++ - ++ ++ ++ + - - - - - + - - - - - - - - ++ - ++ - - + + - + ++ - ++ ++ ++ + ++ - - - - ++ - - - - - - - - ++ - ++ - - ++ + - ++ ++ - ++ ++ ++ + ++ - - - - - - - - - - - - - ++ - ++ - - ++ - - ++ - - - - - - + - - - - - - - - - - - - - - - - - - - - - - - - - - - - + - - - - - - - - - - - - - - - - - - - - - - - - - - - - + - - - - - - - - - - - - - - - - - - - - - - + - ++ + - + ++ ++ + ++ ++ ++ ++ ++ ++ - - ++ ++ ++ ++ - ++ + - ++ + + ++ ++ - ++ ++ - + ++ ++ ++ ++ ++ ++ ++ ++ ++ - - ++ ++ + ++ - ++ ++ - ++ ++ ++ ++ ++ - ++ ++ - + ++ ++ ++ ++ + + ++ - ++ - - ++ - - ++ - ++ ++ - + + - ++ - - ++ - - - + - - - - - - - - - - - - - - - - - - - - - - - - + - - - - - - - - - - - - - - - - - - - - - - - - - - - - ++ - - - + - - - - - - - - - - - - - - - - - - - - - -
The uracil part of compounds that table 2 has been listed the introducing amide structure shown in the general formula of the present invention (I) the inhibition effect that cauline leaf is handled behind soil treatment and the bud before to potted plant examination material plant bud.
Before the seedling during soil treatment, the compound that the broadleaf weed piemarker is shown 80% above weeding activity has: I-01, I-05, I-13, I-23, I-24, I-25, I-27, I-28, I-29, I-45, I-47 under the dosage of 75g ai/ha.
Before the seedling during soil treatment, the compound that the broadleaf weed lamb's-quarters is shown 80% above weeding activity has: I-01, I-05, I-09, I-11, I-14, I-15, I-16, I-17, I-18, I-23, I-24, I-25, I-27, I-28, I-29, I-31, I-36, I-45, I-47, I-53 under the dosage of 75g ai/ha.
Before the seedling during soil treatment, the compound that recessed amaranth of broadleaf weed shown 80% above weeding activity has: I-01, I-05, I-09, I-11, I-13, I-14, I-15, I-16, I-17, I-18, I-23, I-24, I-25, I-27, I-28, I-29, I-31, I-45, I-47, I-50, I-53 under the dosage of 75g ai/ha.
Before the seedling during soil treatment, the compound that the monocotyledon weed lady's-grass is shown 80% above weeding activity has: I-01, I-05, I-09, I-13, I-14, I-15, I-18 under the dosage of 75g ai/ha.
Before the seedling during soil treatment, the compound that monocotyledon weed barnyard grass grass is shown 80% above weeding activity has: I-01, I-05, I-09, I-14 under the dosage of 75g ai/ha.
Before the seedling during soil treatment, the compound that the monocotyledon weed Herba Setariae Viridis is shown 80% above weeding activity has: I-01, I-05, I-09, I-14, I-15 under the dosage of 75g ai/ha.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that the broadleaf weed piemarker is shown 80% above weeding activity had: I-01, I-03, I-04, I-05, I-06, I-09, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-23, I-24, I-27, I-31, I-32, I-34, I-35, I-36, I-37, I-38, I-39, I-42, I-43, I-44, I-45, I-47, I-50, I-53.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that the broadleaf weed lamb's-quarters is shown 80% above weeding activity had: I-01, I-03, I-04, I-05, I-06, I-09, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-23, I-24, I-25, I-27, I-28, I-31, I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-39, I-42, I-43, I-45, I-47, I-48, I-50, I-51, I-52, I-53.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that recessed amaranth of broadleaf weed shown 80% above weeding activity had: I-01, I-05, I-09, I-11, I-12, I-13, I-14, I-15, I-16, I-17, I-18, I-23, I-24, I-25, I-27, I-28, I-31, I-32, I-33, I-34, I-37, I-39, I-42, I-45, I-47, I-48, I-53.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that the monocotyledon weed lady's-grass is shown 80% above weeding activity had: I-01, I-05, I-14, I-15, I-17, I-18, I-27.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that monocotyledon weed barnyard grass grass is shown 80% above weeding activity had: I-01, I-05, I-14.
When cauline leaf was handled behind the bud under the dosage of 75g ai/ha, the compound that the monocotyledon weed Herba Setariae Viridis is shown 80% above weeding activity had: I-01, I-05, I-14, I-15, I-17, I-18, I-27.

Claims (4)

1. introduce the uracil compound of amide structure, the structure shown in (I) that it is characterized in that having general formula:
Figure S200810030588XC00011
X is a hydrogen, fluorine, chlorine;
Y is a hydrogen, fluorine, chlorine;
R 1Be hydrogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
R 2Be hydrogen, C 1-C 4Alkyl, C 1-C 4Haloalkyl;
Q is C 1-C 4Haloalkyl, phenyl, substituted-phenyl, C 1-C 4Alkene oxygen base, C 1-C 4Alkynyloxy group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio, C 1-C 4The phenoxy group that carbalkoxy, halogen, nitro, phenyl replace, substituted pyridines oxygen base, alpha-naphthoxy base.
2. the uracil compound of introducing amide structure according to claim 1, its characterization compound is:
N-(2-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) ethanamide
N-(2-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) propionic acid amide
N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) propionic acid amide
2-(4-chloro-3-methylenedioxy phenoxy)-N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(3-fluorobenzene oxygen) propionic acid amide
N-(2-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2,2-two (3-fluorobenzene oxygen) ethanamide
N-(2-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-tolyl ethanamide
3-chloro-N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2,2-dimethyl propylene acid amides
N-(2,4-two-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide
N-(4-chloro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide
N-(4-fluoro-5-(3-methyl-2,6-dioxy-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1 (6H)-yl) phenyl)-2-(2,4-two-chlorobenzene oxygen) propionic acid amide
2-(4-tert-butyl benzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(m-toluene oxygen)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(4-oil of mirbane oxygen)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(2-anisole oxygen)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(4-fluoro-2-oil of mirbane oxygen)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(4-phenyl benzene oxygen)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(3-fluorobenzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(3,5,6-trichloropyridine-2-base oxygen base)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(3,5,6-trichloropyridine-2-base oxygen base)-N-(2-fluoro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(3,5-dimethyl benzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(4-phenyl benzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl)-2-benzene oxygen propionic acid amide
2-(4-chloro-3-methylenedioxy phenoxy)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
2-(3,5-two (trifluoromethyl) benzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide
N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl)-2-(third-2-alkynes oxygen) propionic acid amide
2-(4-(methylthio group) benzene oxygen)-N-(2,4-two chloro-5-(4-(trifluoromethyl)-2,3-dihydro-3-methyl-2,6-uracil-1 (6H)-yl) phenyl) propionic acid amide.
3. the preparation method of the uracil compound of introducing amide structure according to claim 1 and 2 is characterized in that:
Figure S200810030588XC00031
Add a certain amount of raw material A and triethylamine in the organic solvent ethylene dichloride, the frozen water cooling drips the acyl chlorides B of respective amount down, dropwises, and obtains general formula (I) compound in 1-6 hour in room temperature reaction to the solvent refluxing temperature; Mol ratio is A: acyl chlorides B: triethylamine=1: 1～1.2: 1.1～1.3.
4. the uracil compound of introducing amide structure according to claim 1 and 2, it is characterized in that: when cauline leaf is handled behind soil treatment or the seedling before the seedling under the dosage of 75g ai/ha, piemarker, lamb's-quarters, recessed broadleaf weed such as amaranth are shown weeding activity more than 80%, part monocotyledon weeds such as lady's-grass, barnyard grass grass and Herba Setariae Viridis are also had certain preventive effect.
CNA200810030588XA 2008-02-02 2008-02-02 Uracil weeding compounds introducing amide structure Pending CN101230042A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CNA200810030588XA CN101230042A (en) 2008-02-02 2008-02-02 Uracil weeding compounds introducing amide structure

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CNA200810030588XA CN101230042A (en) 2008-02-02 2008-02-02 Uracil weeding compounds introducing amide structure

Publications (1)

Publication Number Publication Date
CN101230042A true CN101230042A (en) 2008-07-30

Family

ID=39896909

Family Applications (1)

Application Number Title Priority Date Filing Date
CNA200810030588XA Pending CN101230042A (en) 2008-02-02 2008-02-02 Uracil weeding compounds introducing amide structure

Country Status (1)

Country Link
CN (1) CN101230042A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015514723A (en) * 2012-04-12 2015-05-21 ドンブ ファーム ハンノン カンパニー リミテッド Herbicidal composition containing uracil compound as active ingredient
CN105985246A (en) * 2015-03-05 2016-10-05 湖南化工研究院有限公司 Diphenyl-ether compound with weeding or insecticidal or bactericidal activity

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015514723A (en) * 2012-04-12 2015-05-21 ドンブ ファーム ハンノン カンパニー リミテッド Herbicidal composition containing uracil compound as active ingredient
CN105985246A (en) * 2015-03-05 2016-10-05 湖南化工研究院有限公司 Diphenyl-ether compound with weeding or insecticidal or bactericidal activity
CN105985246B (en) * 2015-03-05 2018-04-10 湖南化工研究院有限公司 Has the diphenyl ether compound of weeding, desinsection or bactericidal activity

Similar Documents

Publication Publication Date Title
CN103081916B (en) Application of pyrazole amide compound as agricultural bactericide
CN107205392A (en) The phenyl pyrimidine class of weeding
CN113402510B (en) Condensed ring substituted aromatic compound, preparation method thereof, weeding composition and application
CZ12596A3 (en) Substituted 2-phenylpyridine, process of its preparation, intermediates for its preparation and a herbicidal agent in which the compound is comprised
TW201029573A (en) Novel halogen-substituted compounds
RU2670439C2 (en) Substituted pyrazolyl pyrazole derivative and use thereof as herbicide
CN101817799B (en) Cyanoacrylate compound and application thereof in pesticide and medicine
WO2020063756A1 (en) Triazole compound and use thereof in agriculture
CN101230042A (en) Uracil weeding compounds introducing amide structure
CN110128352A (en) Pyridazine alcohol compound and its derivative, preparation method, Herbicidal combinations and application
CN110878081A (en) Pyridinyl ring substituted pyridazinol compound and derivative, preparation method, herbicidal composition and application thereof
CN101421230A (en) Novel phenyl-propargylether derivatives
CN105693771B (en) Phosphonate ester compound and its preparation method and application containing pyrimidine ring
EP0851858B1 (en) Substituted 2-phenylpyridines as herbicides
AU2017388277A1 (en) Agricultural chemicals
BR0312835B1 (en) 3-Heterocyclyl Substituted Benzoic Acid Derivative, Agent, Unwanted Vegetation Fighting and Plant Desiccation / Defoliation, and Use of 3-Heterocyclyl Substituted Benzoic Acid Derivatives
CN100475034C (en) Use of phenethyl acrylamides, novel phenethyl acrylamides, method for producing same and composition contg. same
CN101165057B (en) Nbeta-substituted phenyluracil compounds for removing glass
CN101704790B (en) Phytocidal N-uracil-substituted phenyl aryloxy-alkyl amide compound
JP2022515285A (en) R-pyridyloxycarboxylic acid, its salt, its ester derivative, its preparation method, its herbicidal composition and its use
RU2693467C2 (en) Derivative of substituted pyrazolyl pyrazole and use thereof as herbicide
CN106478613B (en) 2- [4- (pyridine -2- base oxygroup) phenoxy group] amide derivatives and the preparation method and application thereof
CN112979628B (en) Diphenyl ether substituted oxime derivative and its application in agriculture
CN100390141C (en) Novel propargylether derivatives for controlling phytopathogenic microorganisms
CN103980223B (en) 2-substituent group-5-substituted anilinic-1,3,4-diazoles derivant and synthetic method thereof and application

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Open date: 20080730