Lian Ee Khoo

Fungicidal activity of some organotin compounds against ceratocystis ulmi

Three series of organotin compounds were screened in vitro against Ceratocystis ulmi, the causative agent of Dutch elm disease. The series that were most active against this deadly fungus were those that contained the triphenyltin moiety. In addition, the fungicidal activity of the triphenyltin compounds were found to be independent of the anionic group attached to the tin atom. However, there was a marked increase in the activity of the triphenyltins when a biologically active group which did not dissociate upon dissolution was incorporated into the overall molecule.

The crystal structures of tributyltin and triphenyltin esters of 2-benzoylbenzoic acid

Abstract Tin-199m Mossbauer parameters and IR spectra for triorganotin 2-benzoylbenzoates indicate a trans-C3SnO2 trigonal bipyramidal geometry in the solid state. This configuration was confirmed by X-ray diffraction. Molecules of tributyltin 2-benzoylbenzoate and triphenyltin 2-benzoylbenzoate are ketonic oxygen-bridged into a polymeric chain; the carboxylate carbonyl oxygen is not involved in coordination.

8-Methylaminoquinolinium Salts of Tetrachlorodimethylstannate(IV) and Tetrachlorodiphenylstannate(IV)

The title compounds, (C10H11N2)2[SnCl4(CH3)2] and (C10H11N2)2[SnCl4(C6H5)2], have been prepared from the reaction of 8-methylaminoquinoline with diorganotin dichlorides. In the methyl compound, the Sn atom is coordinated to two methyl groups, which are trans with respect to each other [Sn—C 2.102 (5) and 2.103 (4) A], and to four Cl atoms [Sn—Cl 2.442 (1), 2.461 (1), 2.894 (1) and 3.098 (1) A]. The two long Sn—Cl bonds are trans to the short ones and their Cl atoms are hydrogen bonded to the N—H groups of the 8-methylaminoquinolinium cations. The Sn—CH3 bonds are bent away from the short Sn—Cl bonds so that the CH3—Sn—CH3 angle is 155.7 (2)°. A correlation between the C—Sn—C angle and the Sn—Cl bond lengths was observed. The anion of the phenyl compound is close to being octahedral and has exact twofold symmetry; the phenyl groups are trans with respect to each other [Sn—C 2.143 (2) A] and Sn—Cl distances are in the range 2.497 (1)–2.672 (1) A. Two Cl atoms are hydrogen bonded to N—H groups of the cations.

Crystal structures of chloro[4-bromo-2-(dimethylamino-2-ethyl)aminomethylphenolato]diphenyltin(IV) and dichloro[4-bromo-2-(2'-dimethylaminoethyl)-iminomethylenephenolato]phenyltin(IV)

Figure 1. ORTEP plot of [(CHjkNCIIjCHjNHCHj]2-Br-4-C6H3OSn(C6H,)2Cl at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii. Selected bond distances and angles: Snl-Cli 2.517(2), Snl-Cl 2.158(4). Snl-C7 2.182(4). Snl-Nl 2.274(6). Snl-N2 2.465(7). Snl-Ol 2.048(5) A; CI Snl € 7 106.0(2).Cl-Sn) N1 160.9(2). Cl-Snl-N2 87.7(2). Cl -Snl -Ol 93.4(2). Cl-Snl-Cl l 97.5(1), C7-Snl-Nl 92.9(2). C7-Snl-N2 166.3(2). C7-Snl-01 93.6(2). C7-Snl-Cll 94.5(1). Nl-Snl-N2 73.4(2), N l -Sn l -Ol 82.6(2). Nl-Snl-Cl l 83.3(1). N2-Snl-01 85.3(2). N2-Snl-Cll 83.6(2). Ol Snl-Cll 164.1(2)°. Figure 2. ORTEP plot of [(CH3)2NCH2CH2N=CH|-2Rr-4-C6H3OSn(C6H,)CI2 at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitraryradii. Selected bond distances and angles: Snl CI 2.139(5). Snl N1 2.185(9), Snl-N2 2.32(1). Snl-Ol 2.041(9). Snl-Cll 2.483(3). Snl-C12 2.453(4) A; C l -Sn l -Nl 175.6(3). Cl -Snl -N2 98.3(3). CI-Snl -Ol 98.4(3). Cl -Snl -Cl l 95.8(2). Cl-Snl-C12 95.8(2). Nl -Sn l -N2 77.4(4). Ν1-Snl-Ol 86.0(4). Nl -Snl -Cl l 84.9(3). N1 Snl C12 83.6(3), N2-Snl -01 163.3(4), N2-Snl-Cl 1 90.1(3). N2-Snl-C12 89.0(3). Ol-Snl-CI 1 88.0(3). 01-Snl-CI2 89.6(3). CI 1-Snl -CI2 168.4(1)°

A METHANOL-SOLVATE ADDUCT OF CHLOROTRIPHENYLTIN(IV) WITH 4-BROMO-2-[(DIMETHYLAMINOETHYL)AMINOMETHYL]PHENOL

Figure 1. ORT Ε Ρ plot of (C6H5)3SnCIO-C6H3Br-2-CH2NH2CH2CH2N(CH3)2 C H 3 O H at t he 5 0 % probability level. Hydrogen atoms are drawn as spheres of arbitrary radii. Selected bond distances and angles: S n l C l =2 .122(4 ) , S n l C 7 = 2.139(5), S n l C I 3 = 2.130(5), S n l O l =2 .176(3 ) , S n l C l l = 2.586(2) Ä; C l S n l C 7 = 116.1(2), C l S n l C 1 3 = 129.6(2), C l S n l O l = 85.8(2), C l S n l C I l = 86.4(1), C 7 S n l C13 = 114.4(2), C 7 S n l 0 1 = 94.2(2), C 7 S n l C l l = 94.5(1), C 1 3 S n l 0 1 = 90.6(2), C 1 3 S n l C l l = 90.0(1), O l S n l C l l = 170.2(1)°.

2-[2-(Dimethylamino)ethylammoniomethyl]-4-nitrophenolate

The structure of the title compound, C 11 H 17 N 3 O 3 , reveals that the intramolecular hydrogen-bonded phenolic H atom has shifted to the amino N atom so that there is an intermolecular hydrogen bond to the phenolic O atom of a neighbouring molecule [N...O 2.644 (3) A], as well as an intramolecular hydrogen bond [N...O 2.662(4) A]. This proton-transfer process is due to the nitro substituent which facilitates the formation of a quinonoid structure for the substituted phenyl ring.

A 1:1 ADDUCT OF AQUACHLOROTRIPHENYLTIN(IV) WITH 8-METHOXYQUINOLINE

Figure 1. ORTEP plot of aquachlorotriphenyltin 8-methoxyquinoline at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii. Selected bond distances and angles: Sn l -Cl = 2.126(4), Snl-C7 = 2.132(5), Snl-C13 = 2.111(4), Snl-Ol = 2.407(4), Snl-Cll = 2.479(2) Ä; C l -Sn l -C7 = 114.4(2), C I S n l C l 3 = 125.5(2), C l -Sn l -Ol = 80.1(2), Cl-Snl-CII = 95.4(1), C7-Snl-C13 = 117.2(2), C7-Snl -01 = 90.0(2), C7-Snl-Cll = 97.9(1), C13-Snl-01 = 83.5(2), C13-Snl-Cll = 93.9(1), Ol -Sn l -Cl l = 172.0(1)°.

8-Ammonioquinolinium Dichloride

The crystals of C9H10N22+.2Cl− contain 8-ammonioquinolinium cations, which are stacked along the c axis, and chloride anions, which occupy the channels between the stacks. There is extensive N—H⋯Cl hydrogen bonding between the cations and anions, as well as weak anion–cation Cl⋯H—C(sp2) interactions.

Chloro{2-[2-(dimethylamino)ethyliminomethyl]phenol}triphenyltin(IV) Benzene Hemisolvate, [SnCl(C6H5)3(C11H16N2O)].0.5C6H6

The coordination geometry of the Sn atom in the title compound is trigonal bipyramid, with the ipso C atoms of the phenyl groups in equatorial and the Cl and O atoms in apical positions. The ligand is bonded to the Sn atom through the phenolic O atom; the hydroxy H atom is shifted towards the imino N atom to give rise to a zwitterion, i.e. 2-[2-(dimethylamino)ethyliminiomethyl]phenolate.

Molecular adduct of dimethyltin dichloride with methyl N-(2-hydroxybenzylidene)alaninate (1:2), [SnCl2(C11H13NO3)2(CH3)2]

The structure of the 2:1 complex of methyl N-(2-hydroxybenzylidene)alaninate with dimethyltin dichloride, dichlorobis(2-{[1-(methoxycarbonyl)ethyl]iminiomethyl}phenolato-O)dimethyltin, has been determined. The coordination of the Sn atom is octahedral, all trans, with bond distances Sn-Cl= 2.599 (1), Sn-O=2.244 (3) and Sn-C= 2.111 (4) A. The ligands are coordinated to Sn through the phenolic O atoms, the hydroxylic H atoms being shifted to the intime N atoms giving rise to a zwitterion. There is intramolecular hydrogen bonding N-H...O=2.628 (4) A