Synthesis, Fungicidal Activity, and Structure Activity Relationship of ß-Acylaminocycloalkylsulfonamides against Botrytis cinerea.

In order to discover new antifungal agrochemicals that could have highly active and novel motifs, thirty-six new 2-acylaminocycloalkylsulfonamides (IV) were synthesized. Their structures were characterized and confirmed by 1H NMR, 13C NMR, IR, MS, elemental analysis and X-ray single crystal diffraction. In vitro and in vivo activities against various Botrytis cinerea strains were evaluated. Bioassay results revealed that most of the title compounds exhibited excellent in vitro fungicidal activity, in which compound IV-26 showed the highest activity against sensitive, low-resistant, moderate-resistant and high-resistant strains of B. cinerea compared with the positive fungicide procymidone. Meanwhile in vivo fungicidal activity of compound IV-31 was better than the commercial fungicides procymidone and chesulfamide in greenhouse trial. The structure activity relationship (SAR) was also discussed and the results were of importance to the structural optimization and development of more potent sulfonamides antifungal agents.

Synthesis of rotenone-O-monosaccharide derivatives and their phloem mobility.

Six monosaccharide derivatives of rotenone were designed and synthesized to assess whether rotenone could become phloem mobile by the addition of a monosaccharide group. Phloem mobility experiments showed that only D-glucose conjugates exhibit phloem transport properties in castor bean (Ricinus communis L.) seedlings. Two D-glucose conjugates, 2-O-ß-D-glucopyranosyldemethylrotenone and 6'-O-ß-D-glucopyranosyldalpanol, had significantly obtained systemicity compared with that of rotenone, and 6'-O-ß-D-glucopyranosyldalpanol was more mobile than 2-O-ß-D-glucopyranosyldemethylrotenone. Coupling with a monosaccharide core is a reasonable method for conferring phloem mobility on insecticides, but phloem mobility is also affected by the parent molecule and the position of the monosaccharide.

Poly[(µ(4)-tetra-zole-1-acetato-κN:N:O:O')silver(I)].

In the title complex, [Ag(C(3)H(3)N(4)O(2))](n), the Ag(I) atom is four-coordinated in a slightly distorted tetra-hedral coordination geometry by two N atoms from two tetra-zole-1-acetate (tza) ligands and two O atoms from the other two tza ligands. The tza ligand bridges two Ag atoms through the carboxyl-ate O atoms and simultaneously binds to the other two Ag atoms through the tetra-zole N atoms, forming a two-dimensional network parallel to (100).

Hexaaqua-nickel(II) 4,4'-(1,2-dihy-droxy-ethane-1,2-di-yl)dibenzoate monohydrate.

In the title compound, [Ni(H(2)O)(6)](C(16)H(12)O(6))·H(2)O, the Ni(II) cation is located on a mirror plane and is coordinated by six water mol-ecules, two of which are also located on the mirror plane, in a distorted octa-hedral geometry. The 4,4'-(1,2-dihy-droxy-ethane-1,2-di-yl)dibenzoate anion is centrosymmetric with the mid-point of the central ethane C-C bond located on an inversion center. The uncoordinated water mol-ecule is located on a mirror plane. Extensive O-H⋯O hydrogen bonding is present in the crystal structure.

Diaqua-bis-(4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ato-κN,O)cobalt(II) N,N-dimethyl-formamide disolvate.

In the title complex, [Co(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Co(II) cation (site symmetry ) is six-coordinated by two 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate ligands and two water mol-ecules in a distorted octa-hedral environment. In the crystal structure, the complex mol-ecules and dimethyl-formamide solvent mol-ecules are linked by extensive O-H⋯O and N-H⋯O hydrogen bonding into sheets lying parallel to (21).

Tetra-aquabis(6-carboxy-1H-benzimid-azole-5-carboxyl-ato-κN)nickel(II) dimethyl-formamide disolvate dihydrate.

The title compound, [Ni(C(9)H(45)N(2)O(4))(2)(H(2)O)(4)]·2C(3)H(7)NO·2H(2)O, has the Ni(II) center coordinated by four water mol-ecules and two N atoms from two 1H-benzimidazole-5,6-dicarboxyl-ate ligands in an octa-hedral geometry. The mol-ecule inter-acts with the solvent water and dimethyl-formamide mol-ecules through N-H⋯O and O-H⋯O hydrogen bonds to form a three-dimensional supra-molecular network. The metal atom lies on a center of inversion.

Penta-aqua-(1H-benzimidazole-5,6-dicarboxyl-ato-κN)nickel(II) penta-hydrate.

In the title mononuclear complex, [Ni(C(9)H(4)N(2)O(4))(H(2)O)(5)]·5H(2)O, the Ni(II) atom is six-coordinated by one N atom from a 1H-benzimidazole-5,6-dicarboxyl-ate ligand and by five O atoms from five water mol-ecules and displays a distorted octa-hedral geometry. Inter-molecular O-H⋯O hydrogen-bonding inter-actions among the coordinated water mol-ecules, solvent water mol-ecules and carboxyl O atoms of the organic ligand and additional N-H⋯O hydrogen bonding lead to the formation of a three-dimensional supra-molecular network.

catena-Poly[[diaqua-(1,10-phenanthroline-κN,N')nickel(II)]-µ-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O].

In the title complex, [Ni(C(9)H(4)N(2)O(4))(C(12)H(8)N(2))(H(2)O)(2)](n), the Ni(II) atom is hexa-coordinated by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxyl-ate ligands, two N atoms from one 1,10-phenanthroline ligand and two water mol-ecules. The flexible 1H-benzimidazole-5,6-dicarboxyl-ate ligands link the Ni(II) centres, forming an infinite zigzag chain parallel to [001]. The crystal packing is governed by inter-molecular hydrogen-bonding inter-actions of the O-H⋯O, N-H⋯O and C-H⋯O types.

Penta-aqua-(1H-benzimidazole-5,6-di-carboxyl-ato-κN)cobalt(II) penta-hydrate.

In the title mononuclear complex, [Co(C(9)H(4)N(2)O(4))(H(2)O)(5)]·5H(2)O, the Co(II) atom exhibits a distorted octa-hedral geometry involving an N atom of a 1H-benzimidazole-5,6-dicarboxyl-ate ligand and five water O atoms. A supra-molecular network is generated through inter-molecular O-H⋯O hydrogen-bonding inter-actions involving the coordinated and uncoordinated water mol-ecules and the carboxyl O atoms of the organic ligand. An inter-molecular N-H⋯O hydrogen bond is also observed.

Poly[diaqua-µ(2)-isonicotinato-µ(2)-oxalato-terbium(III)].

In the crystal structure of the title complex, [Tb(C(6)H(4)NO(2))(C(2)O(4))(H(2)O)(2)](n), the Tb(III) cation is coordinated by four O atoms from two oxalate ligands, two O atoms from two isonicotinate ligands and two O atoms from water mol-ecules within a distorted square-anti-prismatic coordination. The Tb(III) cation, the isonicotinate anion and the two crystallographically independent water mol-ecules occupy general positions, whereas one of the two crystallographically independent oxalate anions is located on a center of inversion, and the second oxalate anion is located on a twofold rotation axis. The Tb(III) cations are linked by the oxalate and isonicotinate anions into layers, which are connected via inter-molecular hydrogen-bonding and π-π stacking [with centroid-to-centroid distances of 3.509 (2) and 3.343 (3) Å] inter-actions into a three-dimensional network.