TABLE 2.

GC-MS data for TMS derivatives of products formed by phthalate-induced A. keyseri 12B

Substrate/TMS-derivatized product (retention time)	m/z of major ion peaks (% intensity, proposed composition)a
2-Chlorobenzoate/2-chloro-3,4-dihydroxybenzoate (18.24 min)	406 (6, M+); 404 (11, M+); 391 (5, [M − CH3]+); 389 (11, [M − CH3]+); 317 (2, [M − OTMS]+); 315 (6, [M − OTMS]+); 301 (2); 257 (2); 237 (10, [M − TMS − CO2 −Cl − CH3]+); 227 (100, [M − OTMS − TMS − CH3]+); 193 (3); 171 (6); 147 (3); 73 (86, [TMS]+)
2-Bromobenzoate/2-bromo-3,4-dihydroxybenzoate (19.25 min)	450 (16 M+); 448 (14, M+); 435 (14, [M − CH3]+); 433 (12, [M − CH3]+); 361 (7, [M − OTMS]+); 359 (6, [M − OTMS]+); 347 (4, [M − TMS − CH3 − CH3]+); 345 (3, [M − TMS − CH3 − CH3]+); 303 (4, [M − TMS − TMS − H]+); 301 (3, [M − TMS − TMS − H]+); 273 (100, [M − OTMS − TMS − TMS − CH3]+); 271 (94, [M − OTMS − TMS − CH3]+); 237 (13, [M − TMS − CO2 − Br − CH3]+); 217 (4); 215 (4); 209 (2); 207 (2); 193 (4); 179 (2); 73 (89, [TMS]+)
2-Iodobenzoate/2-iodo-3,4-dihydroxybenzoate (20.50 min)	496 (17, M+); 481 (10, [M − CH3]+); 407 (4, [M − OTMS]+); 393 (2, [M − TMS − CH3 − CH3]+); 354 (3, [M − I − CH3]+); 339 (6, [M − I − CH3 − CH3]+); 319 (100, [M − OTMS − TMS − CH3]+); 266 (6, [M − I − TMS − CH3 − CH3]+); 237 (3, [M − I − TMS − CO2 −CH3]+); 207 (3); 193 (3); 164 (7); 147 (3); 133 (3); 73 (50, [TMS]+)
2-Nitrobenzoate/2-nitro-3,4-dihydroxybenzoate (26.06 min)	415 (4, M+); 400 (38, [M − CH3]+); 385 (1, [M − CH3 − CH3]+); 312 (4, [M − TMS − CH3 − CH3]+); 238 (30, [M − OTMS − TMS − CH3]+); 164 (9, [M − OTMS − OTMS − TMS]+); 147 (9, [M − OTMS − TMS − CO2 − NO2]+); 133 (6); 73 (100, [TMS]+)
2-Trifluoromethylbenzoate/2-trifluoromethyl-3,4-dihydroxybenzoate (16.47 min)	438 (9, M+); 423 (3, [M − CH3]+); 349 (1, [M − OTMS]+); 331 (10); 309 (1, [M − TMS − CO2]+; 261 (11, [M − OTMS − TMS − CH3]+); 239 (100, [M − TMS − TMS − CH3 − F − F]+); 217 (3); 203 (2); 155 (6); 77); 73 (65, [TMS]+)
2-Acetylbenzoate/2-acetyl-3,4-dihydroxybenzoate (25.33 min)	412 (7, M+); 397 (51, [M − CH3]+); 353 (3, [M − CH3 − CH3CO − H]+); 323 (5, [M − OTMS]+); 307 (23, [M − OTMS − CH3CH3 − H]+); 279 (10, [M − OTMS − CH3CO − H]+); 235 (10, [M − OTMS − TMS − CH3]+); 147 (14); 133 (5); 73 (100, [TMS]+)
o-Anisate/2-methoxy-3,4-dihydroxybenzoate (21.76 min)	400 (11, M+); 385 (19, [M − CH3]+); 355 (6, [M − CH3 − CH3 − CH3]+); 311 (6, [M − OTMS]+); 295 (18, [M − TMS − CH3OH]+); 281 (8, [M − OTMS − CH3 − CH3]+); 223 (100, [M − OTMS − TMS − CH3]+); 208 (8); 73 (94, [TMS]+)
2-Chloro-6-fluorobenzoate/2-chloro-(3 or 4)- hydroxy-6-fluorobenzoate (14.135 min) [major product, > 90%]	336 (3, M+); 334 (9, M+); 321 (23, [M − CH3]+); 319 (52, [M − CH3]+); 247 (2, [M − OTMS]+); 245 (3, [M − OTMS]+); 241 (4); 211 (7, [M − TMS − CH3 − Cl]+); 209 (6); 183 (5); 179 (6); 167 (6, M − TMS − CO2 − Cl − CH3]+); 153 (6, [M − TMS − TMS − Cl]+); 137 (7, [M −OTMS − TMS − Cl]+); 105 (6); 93 (14, [M − OTMS − TMS − CO2 − Cl]+); 77 (91); 73 (100, [TMS]+)
2-Chloro-6-fluorobenzoate/2-chloro-3,4-dihydroxy-6-fluorobenzoate (17.50 min)	424 (6, M+); 422 (14, M+); 409 (7, [M − CH3]+); 407 (16, [M − CH3]+); 333 (1, [M − OTMS]+); 321 (2, [M − TMS − CH3 − CH3]+); 319 (6, [M − TMS − CH3 −CH3]+); 255 (2, [M − TMS − CO2 − Cl − CH3]+); 247 (27, [M − OTMS − TMS − CH3]+); 245 (74, [M − OTMS − TMS − CH3]+); 189 (2); 147 (2); 93 (4); 77, (6); 73 (100, [TMS]+)
2,6-Dichlorobenzoate/2,6-dichloro-(3 or 4)-hydroxybenzoate (20.97 min) [major product], LH-20 peak 1	352 (8, M+); 350 (10, M+); 337 (33, [M − CH3]+); 335 (46, [M − CH3]+); 263 (17, [M − OTMS]+); 261 (23, [M − OTMS]+); 227 (11, [M − TMS − CH3 − Cl]+); 225 (10, [M − TMS − CH3 − Cl]+); 185 (5); 183 (12); 95 (14); 93 (38); 73 (100, [TMS]+)
2,6-Dichlorobenzoate/2-chloro-3,4-dihydroxybenzoate (23.37 min), LH-20 peak 1	406 (10, M+); 404 (19, M+); 391 (5, [M − CH3]+); 389 (10, [M − CH3]+); 317 (4, [M − OTMS]+); 315 (9, [M − OTMS]+); 229 (19, [M − OTMS − TMS − CH3]+); 227 (52, M − OTMS − TMS − CH3]+); 199 (4); 179 (4); 147 (4); 93 (3); 73 (100, [TMS]+)
2,6-Dichlorobenzoate/2,6-dichloro-3,4-dihydroxy-3,4-dihydrobenzoate (23.53 min), LH-20 peak 1	442 (2, M+); 440 (3, M+); 407 (10, [− Cl]+); 405 (20, [M − Cl]+); 337 (4, [M − TMS − CH3 − OH]+); 335 (5, [M − TMS − CH3 − OH]+); 325 (2, [M − TMS − CO2]+); 323 (3, [M − TMS − CO2]+); 265 (3); 263 (7, [M − OTMS − TMS − OH]+); 261 (8, [M − OTMS − TMS − OH]+); 243 (3); 227 (3); 187 (3); 161 (5); 147 (21); 93 (11); 75 (16); 73 (100, [TMS]+)
2,6-Dichlorobenzoate/2,6-dichloro-(3 or 4)-hydroxybenzoate (20.87 min), LH-20 peak 2	352 (8, M+); 350 (11, M+); 337 (36, [M − CH3]+); 335 (48, [M − CH3]+); 263 (17, [M − OTMS]+); 261 (24, [M − OTMS]+); 227 (12, [M − TMS − CH3 − Cl]+); 225 (12, [M − TMS − CH3 − Cl]+); 183 (13); 160 (6); 153 (6); 123 (3); 95 (13); 93 (34); 73 (100, [TMS]+)
2,6-Dichlorobenzoate/2,6-dichloro-3,4-dihydroxybenzoate (25.26 min), LH-20 peak 2	440 (7, M+); 438 (9, M+); 425 (3, [M − CH3]+); 423 (5, [M − CH3]+; 351 (4, [M − OTMS]+); 349 (5, [M − OTMS]+); 273 (2, [M − TMS − CO2 − CH3 − Cl]+); 271 (5, [M − TMS − CO2 − CH3 − Cl]+); 265 (6); 263 (32, [M − OTMS − TMS − CH3]+); 261 (42, [M − OTMS − TMS − CH3]+); 147 (4); 93 (5); 73 (100, [TMS]+)

^aPaired ions differing by two mass units result from major chlorine isotopes of mass 35 and 37 and bromine isotopes of mass 79 and 81.