Synthesis, Crystal Structure and Fungicidal Activity of 3-(Difluoromethyl)-1-methyl-N-((2-(trifluoromethyl)phenyl) carbamoyl)-1H-pyrazole-4-carboxamide

The title compound 3-(difluoromethyl)-1-methyl-N-((2-(trifluoromethyl)phenyl)-carbamoyl)-1 H-pyrazole-4-carboxamide(C14 H11 F5 N4 O2) was synthesized, and its structure was confirmed by 1 H NMR, H RMS and X-ray diffraction. It crystallizes in monoclinic system, space group P21/n with a = 6.994(3), b = 13.860(6), c = 15.308(7)A,β= 97.632(6)°, V = 1470.8(11) A^3,Z = 4, the final R = 0.0692 and wR = 0.2108 for 3989 observed reflections with Ⅰ> 2σ(Ⅰ). The preliminary biological test shows that the title compound has moderate fungicidal activities against Pseudomonas syringae.

Synthesis, Crystal Structure and Fungicidal Activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl)propionamide

The title compound has been synthesized by the reaction of 4-tert-butyl-5-（1,2,4- triazol-1-yl）-2-aminothiazole with propionic anhydride, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group Pbca with α = 18.441（2）, b = 8.3284（9）, c = 19.257（2） A, Z = 8, V = 2957.5（5） A3, Mr = 279.37, Dc = 1.255 mg/m3, S = 1.033, μ =0.219 mm^-1, F（000） = 1184, the final R = 0.0349 and wR = 0.0876 for 2629 observed reflections （I 〉 2σ（I））. X-ray crystal structure presents the intermolecular N–H···N hydrogen bond, which plays an important role in stabilizing the crystal structure. The preliminary bioassay indicates that the title compound exhibits potent fungicidal activity against R. Solani （25 mg/L） with inhibition rate of 80.0%.

Synthesis, Crystal Structure and Fungicidal Activity of (Z)-3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-2-Chlorobenzyl Oxime Nitrate

The title compound has been synthesized by the reaction of 3,3-dimethyl-1-（1H-1,2,4-triazol-1-yl）butan-2-one oxime with 2-chlorobenzyl chloride, and then treated with 65～68% HNO3. Its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 14.5481（8）, b = 9.3351（5）, c = 13.1911（7） , β = 98.9450（10）°, Z = 4, V = 1769.67（17） 3, Mr = 369.81, Dc = 1.388 g/cm3, S = 1.06, μ = 0.247 mm-1, F（000） = 776, the final R = 0.0352 and wR = 0.0960 for 3069 observed reflections （I 2σ（I））. X-ray crystal structure presents the intramolecular N–H…O hydrogen bond. The packing is nearly parallel without π-π stacking interactions between two adjacent phenyl rings and stabilized by Van der Waals force. The preliminary bioassay shows that the title compound possesses fungicidal activity against Gibberella zeae at the dosage of 25 mg/L.

Synthesis, Crystal Structure and Fungicidal Activity of Ethyl 2-(3-(4-Fluorobenzamido)phenyl)-4-((4-fluorobenzoyl)oxy)thiazole-5-carboxylate

The target compound,ethyl 2-(3-(4-fluorobenzamido)phenyl)-4-((4-fluorobenzoyl)oxy)thiazole-5-carboxylate,was synthesized by four-step procedures including N-protection,thionation,cyclization and acylation.Its structure was characterized by 1 H NMR,13C NMR,HRMS and single-crystal X-ray diffraction.The target compound crystallizes as monoclinic crystal system,space group C2/c with a=9.6097(19),b=14.246(3),c=33.070(7)A,V=4515.1(16)A3,Z=8.Dc=1.496 Mg/m3,F(000)=2096 andμ=0.203 mm-1.There are 21864 reflections measured(4.94≤2θ≤55.96°),of which 5357 were unique(Rint=0.1418)and used in all calculations.The final R=0.0581(I>2δ(I))and wR=0.1453(reflections).The target compound showed over 50%of growth inhibition against Physalospora piricola,Rhizoctonia cere al is and Sclerotinia sclerotiorum.

Synthesis,Crystal Structure and Antifungal Activity of 2-((2-Fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole

The title compound 2-（（2-fluorobenzyl）thio）-5-（pyridin-4-yl）-1,3,4-oxadiazole（C_（14）H_（10）FN_3OS） was synthesized,and its structure was confirmed by ~1H NMR,MS,elemental analyses and X-ray diffraction. It crystallizes in the monoclinic system,space group P21/n with a = 11.541（16）,b = 8.226（12）,c = 13.683（19） ？,β = 94.872（17）o,V = 1294（3） ？~3,Z = 4 and R = 0.0648 for 2198 observed reflections with I 〉 2σ（I）. The preliminary biological test shows that the title compound has good activity against Pythium ultimum with inhibitory to be 100%.

Syntheses, Crystal Structures, and Biological Activities of Two 5-Pyrimidinyl-1,2,4-oxadiazoles

Two 5-pyrimidinyl-1,2,4-oxadiazoles were synthesized through two different routes and their structures were characterized by single-crystal X-ray diffraction, NMR and MS. Compound 3, 5-（2-chloro-4-methyl-6-phenylpyrimidin-5-yl）-3-phenyl-1,2,4-oxadiazole, crystallizes in orthorhombic, space group Pbca with a = 19.1575（11）, b = 8.2115（5）, c = 21.2035（12）A, V = 3335.6（3）A3 and Z = 4. Compound 6, 5-（2,6-dichloropyrimidin-4-yl）-3-phenyl-1,2,4-oxadiazole, crystallizes in monoclinic space group Pn with a = 8.4275（13）, b = 5.4088（8）, c = 13.493（2）A, β = 99.768（3）°, V = 4658.6（6）A3 and Z = 8. Preliminary bioassay indicated that the two title compounds had good herbicidal activities.

Synthesis,Crystal Structure and Biological Activity of 2-(Anthracen-9-yl)-5-p-tolyl-1,3,4-oxadiazole

A novel compound,2-（anthracen-9-yl）-5-p-tolyl-1,3,4-oxadiazole（C23H16N2O）,has been synthesized by the condensation of 4-methylbenzohydrazide and anthracene-9-carbaldehyde in an ethanol solution with chloramine-T.The compound was characterized by 1H-NMR,13C-NMR,MS and single-crystal X-ray diffraction.The crystal belongs to the triclinic system,space group P with a = 7.7817（4）,b = 8.8544（5）,c = 12.4726（8） ,β = 92.8520（10）°,Z = 2,V = 826.58（8） 3,Dc = 1.352 g/cm3,Mr = 336.38,λ（MoKα） = 0.71073 ,μ = 0.084 mm-1,F（000） = 352,R = 0.0381 and wR = 0.1099.The dihedral angle between anthracene skeleton and phenyl ring is 64.19°.A total of 6354 unique reflections were collected,of which 3172 with I 〉 2σ（I） were observed.X-ray analysis indicated an offset face-to-face π-π stacking interaction between anthracene skeletons and an offset face-to-face π-π stacking interaction between phenyl ring planes.The novel compound molecules are connected through the offset face-to-face π-π stacking interactions to generate a three-dimensional network.The preliminary bioassay results showed that the novel compound exhibited significant insect growth inhibitory activity against Spodoptera litura Fabricius larvae.

Microwave Assistant Synthesis and Dimeric Crystal Structure of 2-(((6-Chloropyridin-3-yl)-methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole

The title compound 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-thiadiazole 5(C26H18Cl2N8S4) was synthesized, and its structure was confirmed by 1H NMR, MS and elemental analyses and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 9.452(4), b = 12.335(4), c = 13.017(5) A, α = 90.624(5), β = 110.541(5), γ =104.879(4)°, Dc = 1.561 g/cm3, Z = 2, V = 1364.9(9) A3, F(000) = 656, the final R = 0.0300 and w R = 0.0635 for 4206 observed reflections with I 】 2σ(I). The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici(Enjoji) Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory activities to be 9.82%, 44.44% and 20.00%, respectively.

Synthesis,Crystal Structure and Fungicidal Activity of(E)-2-[(4-tert-Butyl-5-(4-methoxybenzyl)thiazol-2-ylimino)methyl]phenol

The title compound （E）-2-[（4-tert-butyl-5-（4-methoxybenzyl）thiazol-2-ylimino）methyl]phenol was synthesized by the reaction of 5-（4-methoxybenzyl）-4-tert- butylthiazol-2-amine with salicylaldehyde, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 5.9362（8）, b = 11.5070（15）, c = 29.460（4）A, β= 97.326（3）°, V = 1995.9（5） A^3, Z = 4, F（000） = 808, C22H24N2O2S, Mr= 380.49, De= 1.266 g/cm^3, S = 1.031,μ = 0.181 mm^-1, the final R = 0.0474 and wR = 0.1441 for 4327 observed reflections （I 〉 2σ（I））. Intramolecular O-H…N hydrogen bond is observed in the crystal. The preliminary bioassay showed that the title compound exhibits 95% inhibition rate against Rhizoctonia solani at the test concentration of 500 mg/L.

Synthesis, Crystal Structure and Biological Activity of 5-(2-Methylphenyl)-1,3,4-oxadiazol-2(3H)-one Derivatives

3-Methyl-5-（2-methylphenyl）-1,3,4-oxadiazol-2（3H）-one （6） and N,N-diethyl-2-（2- methylbenzoyl）-hydrazinecarboxamide （7） were designed and synthesized from 5-（2-methyl- phenyl）- 1,3,4-oxadiazol-2（3H）-one （5） by substituting and ring-opening, respectively. The target compounds were confirmed by IR, JH NMR spectroscopy, MS, elemental analysis and single-crystal X-ray diffraction. Compound 6 （Cl0Hl0N202, Mr = 190.20） crystallizes in the triclinic system, space group P1 with a = 7.4645（16）, b = 10.868（2）, c = 12.970（3） A, α= 110.542（2）, β= 98.142（2）, γ= 99.766（2）°, V = 947.7（3） A3, Z = 4, F（000） = 400, Dc = 1.333 g/cm3, μ = 0.095 mm-1, the final R = 0.0550 and wR = 0.1483 for 2956 observed reflections with I〉 2σ（1）. Compound 7 （C13HI9N302, Mr = 249.31） crystallizes in the monoclinic system, space group C2/e with a = 18.926（3）, b = 12.1853（17）, e = 14.740（2） A, fl = 125.6380（10）~, V= 2762.7（7） A3, Z = 8, F（000） = 1072, Dc = 1.199 g/cm3,μ = 0.083 mm-1, the final R = 0.0554 and wR = 0.1468 for 2395 observed reflections with I 〉 2σ（I）. The preliminary bioassay results indicate that compound 6 exhibits notable fungicidal activities against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici at the concentration of 100 μg/mL.

Synthesis, Crystal Structure, Docking and Antifungal Activity of a New Pyrazole Acylurea Compound

The title compound N-（（3,5-dimethylphenyl）carbamoyl）-1-methyl-3-（trifluoromethyl）-1 H-pyrazole-4-carboxamide（C（15）H（15）F3N4O2） was synthesized, and its structure was confirmed by 1 H NMR, H RMS and X-ray diffraction. It crystallizes in the triclinic system, space group P1 with a = 11.7147（5）, b = 11.7935（5）, c = 13.6620（5） A, α = 69.755（7）°, β = 66.182（6）°, γ = 72.100（7）°, Dc = 1.423 g/cm^3, Z = 4, V = 1588.88（11） A^3, the final R = 0.0347 and wR = 0.1005 for 7171 observed reflections with I 〉 2σ（I）. The preliminary biological test showed that the title compound has antifungal activities against Fusarium oxysporum, Pseudomonas syringae, Corynespora mazei and Botrytis cinerea at 100 μg/mL as 5.19%, 53.50%, 88.55% and 70.62%, respectively. The docking results indicated the hydrogen bonds formed between the compound and SHD.

Synthesis, Crystal Structure and Biological Activity of 1,5-Bis(4-methoxyphenyl)-3-(4-methyl-1,2,3-thiadiazol-5-yl)pentane-1,5-dione

The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.

Microwave Assistant Synthesis,Crystal Structure and Biological Activity of 1-(2-Fluorobenzyl)-3-methoxy-4-methyl-1H-1,2,4-triazol-5(4H)-one

The title compound 1-（2-fluorobenzyl）-3-methoxy-4-methyl-lH-1,2,4-triazol- 5（4H）-one （CI1HI2FN302） was synthesized, and its structure was confirmed by 1H NMR, IR, MS, elemental analysis and X-ray diffraction. It crystallizes in the monoclinic system, space group Pi with a = 6.919（3）, b = 8.525（4）, c = 9.811（4） A, a = 84.22（2）, β = 71.028（19）, γ = 86.10（2）°, Dc = 1.448 g/cm3, Z = 2, V= 544.2（4） A3, F（000） = 248, the final R = 0.0379 and WR = 0.0913 for 1709 observed reflections with I〉 2σ（I）. The preliminary biological test shows that the title compound shows weak inhibitory activities against Phytophthora infestans, Botrytis cinerea, Corynespora cassiicola, Rhizoctonia solani and Pythium ultimum.

Synthesis, Crystal Structure and Fungicidal Activity of 2-Chloro-N-(o-tolylcarbamoyl)nicotinamide

The title compound 2-chloro-N-(o-tolylcarbamoyl)nicotinamide(C(14)H(12)ClN3O2) was synthesized, and its structure was confirmed by ~1H NMR, H RMS and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/n with a = 7.8356(7), b = 12.7949(8), c = 13.6326(10) ?, β = 91.929(7)°, V = 1365.97(18) ?~3, Z = 4, the final R = 0.0416 and wR = 0.0971 for 2467 observed reflections with I > 2σ(I). The preliminary biological test shows that the title compound has certain fungicidal activities.

Synthesis, Crystal Structure and Fungicidal Activity of 3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones

3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2 H-chromen-2-ones,a kind of coumarin derivatives,were synthesized byβ-ketoester formation and cyclization.Target compound 5 e was crystallized from methanol for structural identification as monoclinic crystal system,space group C2/c with a=16.2700(6),b=7.1801(5),c=23.4861(10)A,V=2742.6(2)A^(3),Z=8,Dc=1.756 g/cm^(3),F(000)=1456 andμ=0.827 mm-1.8308 Reflections were collected(6.01≤2θ≤50.05°),of which 2428 were unique(Rint=0.0432)and used in all calculations.The final R=0.0408(I>2σ(I))and w R=0.1056(reflections).In vitro bioassay indicated that compounds 5 d&5 e possessed good activity against Botrytis cinerea,Physalospora piricola,Rhizoctonia solani,and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85μg/m L than that of positive control osthole with its EC50 values between 7.38 and 74.59μg/mL.In vivo screening showed that 5 e exhibited 98%and 95%efficacy against Pseudoperonospora cubensis(Berk.&Curt.)Rostov.at 100 and 50μg/mL,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with coumarin was an effective way to novel fungicide development.

Synthesis and Crystal Structure of N-Ferrocenesulfonyl Hexahydropyridine

The title compound （C15H19FeNO2S, Mr = 333.22） was synthesized by the reaction of ferrocenesulfonyl chloride with hexahydropyridine, and characterized by ^1H NMR, IR and elemental analysis. The crystal belongs to monoclinic, space group P21/n with a = 6.0472（5）, b = 20.4897（6）, c = 11.6584（8）A°,β = 91.3120（10）°, V = 1444.16（16） A°^3, Z = 4, Dc= 1.533 g/cm^3, F（000） = 696,μ = 1.188 mm^-1, the final R = 0.0309 and wR = 0.0736 for 2057 observed reflection with I 〉 2σ（I）. The structure analysis demonstrates that two cyclopentadienyl rings are almost parallel with a dihedral angle of 1.70°, and hexahydropyridine moiety exists in a chair conformation. Bioassay indicates that the title compound has a good fungicidal activity.

Synthesis and Crystal Structure of 3-(4-Chlorophenyl)-8-cyano-2-(di-isopropylamino)-5-methyl-7-(methylthio)-pyrido[4,3-d]pyrimidine-4(3H)-one

The crystal structure of the new title compound 3-（4-chlorophenyl）-8-cyano-2-（di-iso-propylamino）-5-methyl-7-（methylthio）-pyrido[4,3-d]pyrimidine-4（3H）-one（C22H24ClN5OS,Mr = 441.97）has been determined by single-crystal X-ray diffraction. The crystal is of orthorhombic,space group Pna21 with a = 7.6721（5）,b = 18.9370（11）,c = 15.6260（9）A,V = 2270.2（2）A^3,Z = 4,Dc = 1.293 g/cm^3,F（000）= 928,μ = 0.283 mm^-1,MoKa radiation（λ = 0.71073 A）,R = 0.0494 and wR = 0.1062 for 3278 observed reflections with I 〉 2σ（I）. X-ray diffraction analysis reveals that all ring atoms in the py-ridopyrimidinone moiety are almost coplanar. Intramolecular C（20）-H（20）···N（4）,C（19）-H（19A）···N（3）,C（18）-H（18C）···N（3）and C（16）-H（16B）···O（5）hydrogen bonds together with weak C···π interactions are found in the structure.

Synthesis and Crystal Structure of N-((6-chloropyridin-3-yl)methyl)-6-ethoxy-N-ethyl-3-nitropyridin-2-amine

The title compound N-（（6-chloropyridin-3-yl）methyl）-6-ethoxy-N-ethyl-3-nitropyri-din-2-amine（4） was synthesized by reacting the mixture of 6-chloro-2-ethoxy-3-nitropyridine（1） and 2-chloro-6-ethoxy-3-nitropyridine（2） with 3,and its structure was determined by X-ray single-crystal diffraction.The crystal belongs to the monoclinic system,space group P21/n with a = 7.3441（2）,b = 9.9041（3）,c = 11.7368（3） ,α = 101.410（2）,β = 102.1340（10）,γ = 99.594（2）o,μ = 0.260 mm^-1,Mr = 336.78,V = 798.58（4）（A°）^3,Z = 2,Dc = 1.401g/cm^3,F（000） = 352,T = 296（2） K,R = 0.0210 and wR = 0.1053.

Synthesis,Crystal Structure and Fungicidal Activity of 3,4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole

3,4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole,a novel purine derivative,was synthesized by the cyclization of pyrimidine amine.Its structure was characterized by ^(1)H NMR,^(13)C NMR,^(19)FNMR,H RMS and single-crystal X-ray diffraction.This compound 3 is crystallized from a mixed solvent of dichloromethane and n-hexane (1:2,v/v) for structural identification as monoclinic crystal system,space group P2_(1)/n with a=11.66250(10),b=8.21300(10),c=17.77920(10)?,V=1676.34(3)?^(3),Z=4,D_(c)=1.643 g/cm^(3),F(000)=832.0 andμ=6.301 mm^(-1).22315 reflections were measured (8.43≤2θ≤158.10°),of which 3532 were unique (R_(int)=0.0311) and used in all calculations.The final R=0.0334 (I>2σ(I)) and w R=0.0842 (reflections).The title compound showed over 50%of growth inhibition against Botrytis cinereal,Cercospora arachidicola,Gibberella zeae,Rhizoctonia solani and Sclerotinia sclerotiorum at 50 mg/L,and its EC_(50) value against R.solani was 60.44μmol/L,which was active at the same level as that of positive control diflumetorim with its EC_(50) value of 60.29μmol/L and less active than YZK-C22 with its EC_(50) value of 12.32μmol/L,respectively.Our studies discovered that the combination of bioactive substructures of isothiazole with purine could be an effective way to novel fungicide development.

Synthesis,Crystal Structure and Antifungal Activity of 4-(5-((2,4-Dichlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine

The title compound 4-（5-（（2,4-dichlorobenzyl）thio）-4-phenyl-4H-1,2,4-triazol-3- yl）pyridine （C20HI4CI2N4S） was synthesized, and its structure was confirmed by 1H NMR, MS, elemental analyses and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/c with a = 14.885（5）, b = 8.597（2）, c = 16.144（5）A,β= 114.505（4）°, V= 1879.8（10） A3, Z= 8 and R = 0.0320 for 3108 observed reflections with I 〉 2σ（I）. The preliminary biological test shows that the title compound has activities against Stemphylium lyeopersici （Enjoji） Yamamoto, Fusarium oxysporum, sp. cueumebrium, and Botrytis cinerea with inhibitory to be 53.57%, 66.67% and 24.44%, respectively.