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Home , Chrysanthemic acid, Hydroprene, Nereistoxin, Oxon (chemical), Pyrethrin I, Pyrethrin II

Chemical Index

Throughout the text of the book , drugs, and other chemicals are frequently referred to only by common name or manufacturers' designation. Since these provide little or no information concerning chemical class or struc• ture, the following index has been compiled to afford the reader simple and rapid access to this information. Chemicals are listed alphabetically by the common names appearing in the text, and the chemical names are in general accordance with the principles of the Chemical Abstract Service of the American Chemical Society. The index was compiled mainly from the following: E. E. Kenaga and W. A. Allison, 1969, Commercial and experimental organic insecticides, Bull. Entomol. Soc. Am. 15 :85. E. Y. Spencer, 1973, Guide to the chemicals used in crop protection, 6th ed., Research Branch, Canada Department of Agriculture, Ottawa, Canada.

715 ~ 0)

Common Name Q ~ or Designation Chemical Name Structure [ :s- C 2H 50 S ° 1} "II II >< Acethion 0,0- Diethyl-S-carboethoxymethyl phosphorodithioate P-SCH 2COC 2 H 5 / C2H50

S S CH30,11 II/OCH 3 Abate 0,0,0',0' -Tetramethyl-O,O' -thiodi-p-phenylene P phosphorothioate CH30/ '0-o-S-o-0/p 'OCH 3

CH3 2-Methyl-2-(methylthio)propionaldehyde• I °II CH3 SC-CH=NOCNHCH 3 O-(methylcarbamoyl)oxime I CH3

CI~2l:;;-- 1,2,3,4,10,10-Hexachloro-l ,4,4a,5,8,8a-hexahydro-l ,4-endo, exo-5,8-dimethanonaphthalene Cl -9 Cl Cl

3 (CH lzC=Cj>-H °~OV CH3 Allethrin dl-2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-l-one ester of cis and trans-dl- (CH3)2 CH2 CH=CH 2 ° CI~2CI CH2C1 Alodan 1,2,3,4,7,7a-Hexachloro-5,6-bis(chloromethyl)-2-norbornene CI CH CI h 2

CI CI

o II ))HCH' 4-Dimethylamino-m-tolyl methylcarbamate

y CH 3 N(CH 3h

H r 3 H3C N Aminopyrine 4-Dimethylamino-l,5-dimethyl-2-phenyl-3-pyrazolone If '~--o~ (CH3hNY----!::.O -

C2 HsO S "IIp Amiton O,O-Diethyl-O-2-diethylaminoethyl phosphorothioate C2HsO / "OCH 2CH2N(C2Hsh

H o NONa 9 (CH3hCHCH2CH2Y-r ~ Amobarbital (sodium) Sodium 5-ethyl-5-isoamylbarbiturate [ HsC?"y :;• o It)(

..., ...,... '-I ~ (X) 9 Common Name Cb or Designation Chemical Name 3 Structure [ :s• Amy tal (See Amobarbital, sodium) ~ '"

Anabasine 1-3-(2' -Piperidyl) pyridine lNr~/~,0

CH 3 1 Antipyrine 1,5-Dimethyl-2-phenyl-3-pyrazolone H3C N U-Do

L'N, ,/ N~ -?,P, Apholate 2,2,4,4,6,6-Hexakis( l-aziridin y1)- 2,2, 4,4,6,6-hexah ydro- 1,3,5,2,4,6-triazatriphosphorine tN,~fJ ,/NJ ,/P~,/N, ~ N NV

Arprocarb (See )

C3H70 S S OC3H7 ,II 11/ Aspon 0,0,0,0- Tetrapropyl dithiopyrophosphate P-O-P / , C3H70 OC3H7 CI NJ--N Atrazine 2-Chloro-4-ethylamino-6-isopropylamino-I,3,5-triazine AJl C2HSHN N NHCH(CH 3h ~ ° II\.. Atropine dl-Tropyl tropate Vo~c~ CH20H

Azinphosethyl O,O-Diethyl analog of azinphosmethyl

CH30,,~:X)0 Azinphosmethyl 0,0- Dimethyl-S-[4-oxo-l ,2,3-benzotriazin-3(4 H)-ylmethyl] P ::? / "S-CH2-~I phosphorodithioate CH 3 0 N,,:::::,.. "N

Azodrin (See )

Banol (See Carbanolate)

H 0yNyONa 9 Barbital (sodium) Sodium 5,5-diethylbarbiturate 3 (C2Hs)~~[ :;• ° ~ ><

..... ~ ID -...j o"->

Common Name Q or Designation Chemical Name Structure ~ ~ S• CI f} CH C >c ( 3h =Cp>-H ~ -Q~ Barthrin 6-Chloropiperonyl ( + )-trans-chrysanthemate COCH2 0 - J (CH 3)2 0

Baygon (See Propoxur)

BHC (See HCH isomers)

Bidrin (See Dichrotophos)

(CH 3 h=CH ~

Bioresmethrin 5-Benzyl-3-furylmethyl ( + )-trans-chrysanthemate ~COCH'CJ-CH'-O (CH 3h °

S CI CH 30,,11 -Q- Bromophos O-(4-Bromo-2,5-dichlorophenyl)-O,O-dimethyl / P, 0 f '\ Br phosphorothioate CH 3 0 _

CI

°II °II Bux Commercial contains mixture of m-(I-methylbutyl)• .J;HCH,,J)HCH, phenyl methylcarbamate and m-(l-ethylpropyl)phenyl methylcarbamate in a 4: 1 ratio V CHC3 H7 VCHC 2 Hs I I CH 3 C2 HS °II Butacarb 3,5-Di-tert-butylphenyl methyl HCH :5 ' (CH3)3C~c(CH3h

°II CL,J)HCH, Carbanolate 6-Chloro-3,4-dimethylphenyl methyl carbamate

VCH 3 CH 3

II 0CNHCH° 1-Naphthyl methylcarbamate ~ 3 06I~ ::::,... ~

C2H50 S "II S-[(p-Chlorophenylthio )methylJ-O,O-diethyl p phosphorodithioate C 2 H 5 0 / "S-CH 2 - S-o-Cl o II ~ OCNHCH3 [ 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (CH3hyO~ :s• g. LV )( -.J '"~ -.,J N N

Common Name [ or Designation Chemical Name Structure [ o ::;• ~ II >c CHzSCNH z Thiocarbamic acid S,S-[2-(dimethylamino)trimethyleneJester / Cartap (CH 3lzNCH HCI hydrochloride "- CHzSCNH z II o

Chlorcyclizine (HCI) 1-(4-Chlorobenzhydryl)-4-methylpiperazine dihydrochloride CI-o~C-NC/"---I ""'-CH,.2HC1

:~IZCl 1,2,4,5,6,7 ,8,8-0ctachl oro-2,3,3a,4, 7,7 a -hexah ydro-4, 7-endo• methanoindene CI Cl .& Cl Cl

Chlordecone (See Kepone)

Cl Chlordene 4,5,6,7,8,8-Hexachloro-3a,4, 7,7a-tetrahydro-4, 7-endo• :W12

methanoindene .& .....:; Cl Cl N' -( 4-Chloro-o-tolyl)-N ,N -dimethylformamidine CI-QN=CHN(CH 3h

CH 3

Chlorfenamidine (See Chlordimeform)

2 s CHO"~ -b-C1 Chlorfen vinphos 0-2-Chloro-l-(2,4-dichlorophenyl)vinyl-O ,O-diethyl phosphate /p" O-C f ~ CI C2 HsO 11- HCCI N~ Chlorpromazine (HCI) lO-(3'-Dimethylaminopropyl)-3-chlorophenothiazine HCI (X ~ I S~CI I CH2CH2CH2N(CH 3h

S CI CH 30,,J1

Chlorthion 0-3-Chloro-4-nitrophenyl-O,O-dimethyl phosphorothioate ...... 0- /p O Ij ~ N0 2 CH 3 0 _

Co-Ral (See )

Coroxon analog of Coumaphos

CH 3 9 3 Coumaphos O,O-Diethyl-O-3-chloro-4-methyl-2-oxo-2H-l• C2HsO,,~-0)"""CI [ benzopyran-7-yl phosphorothioate / ...... 0 ;:) C2 HsO ~ 0 0 ~ '" ..... r.J W ..... I\,) ~

Common Name ~ or Designation Chemical Name Structure r;' !!!. 5- ~ (CH3)2C=~~ Cyclethrin ( ± )-3-(Cyclopent-2-enyl)-4-keto-2-methylcyclopent-2-enyl -yLvCH' >< ( + )-trans-chrysanthemate ~ CO I (CH,h o

Cl 0 2,4-D 2,4-Dichlorophenoxyacetic acid Cl-O-OCH1~OH

ClO I II Dalapon Sodium 2,2-dichloropropionate CH C-C-ONa 3 I Cl

H DDA Bis-p-chlorophenyl acetic acid Cl-G-f-Q-Cl C=O I OH

DDD 2,2-Bis(p-chlorophenyl)-l, I-dichloroethane Cl-G-?-G- Cl HCCl2 DDE 2,2-Bis(p-chlorophenyl)-l, I-dichloroethylene ClOtOCI CCl2

DDMU 2,2-Bis(p-chlorophenyl)-l-chloroethylene CI~C~CI ~II~HCCl

H DDT 2,2-Bis(p-chlorophenyl)-I, I, I-trichloroethane ClO{OCI CCI]

DDVP (See )

Decamethonium Decomethylene-bis(trimethylammonium iodide) [(CH3hN+(CH2)10N+(CH3hJ21 -

C4 H q S 0 ".Ii P DEF S,S,S-Tributyl phosphorotrithioate / ". C4 H 9 S SC4 H 9

Delnav (See )

C 2 H sO 0 ".Ii Demeton O,O-Diethyl-S- (and 0-) 2-[(ethylmercapto)ethylJ P / i phosphorothioates ". C 2 H sO SCH2CH2SC2H s ~ (thiolo isomer) ::;- ~ ><

~ N t7I -..J N CJ)

Common Name 9 or Designation Chemical Name Structure ~ ~ S-• H 0 0 i-C 3 7 ~ >< DFP 0,0- Diisopropyl phosphorofluoridate "IIP

i-C 3 H 7 0 /" F

C 2 HsO" ~ P, N 0,O-Diethyl-0-(2-isopropyl-4-methyl-6-pyrimidyl)• C 2 HsO/ 01l·~CH(CH3h phosphorothioate yN

CH 3 Diazoxon Oxon analog of Diazinon

OH 1,1-Bis(p-chlorophenyl)-2,2,2-trichloroethanol Cl-Q-{-o-Cl CCb

CH3 0 0 CH3 0 "II I II 3-(Dimethoxyphosphinoxy)-N,N-dimethyl-cis-crotonamide P-OC=CHCN(CH 3h / CH30

CH30 0 "II Dichlorvos 0-2,2-Dichlorovinyl-0,0-dimethyl phosphate P

CH3 0 / "OCH=CCI 2 C~ICl'0 (HEOD) 1,2,3,4, 10, 10- Hexachloro-exo-6, 7-epoxy-l ,4,4a,5,6, 7,8,8a• Cl octahydro-l,4-endo, exo-5,8-dimethanonaphthalene h Cl Cl

CH30 s ".11 °,O-dimethyl-S-(N -methylcarbamoylmethyl)• P 0 phosphorodithioate / ". II CH30 SCH2CNHCH 3

Dimethoxon Oxon analog of Dimethoate

CH, (CH,)F=CH 0 h Dimethrin 2,4-Dimethylbenzyl( + )-trans-chrysanthemate ~~OCH2-U-CH'

(CH')2

0 l-(Dimethylcarbamoyl)-5-methyl-3-pyrazolyl o CbH, dimethylcarbamate II II (CH3hNCO-N, h OCN(CH')2 N

~ 0 I S- P-(OC 2HSh Dioxathion 2,3-p-Dioxane(dithiol)-S,S-bis(O,O-diethylphosphoro ( 9 dithioate <

.... N ...... ~

Common Name or Designation Chemical Name Structure i [ S- 1} >c

Diphenylhydantoin 5,5-Diphenyl-2,4-imidazolidinedione sodium ,) O (sodium) v

Dipterex (See Trichlorfon)

CzHsO S "II O,O-Diethyl-S-2-[(ethyIthio)ethyIJphosphorothioate p CzHsO / "SCHz~H2SC2Hs

Disyston (See Disuifoton)

Dithion (See Sulfotep)

OH DMC 4,4'-Dichloro-~-methylbenzhydrol ClO{OCI CH3

S CzHsO,,~-o~ Dyfonate O-Ethyl-S-phenyl ethylphosphonodithioate / 's C 2 H S _ CrulCI 6,7,8,9,10,10-Hexachloro-1,5,5a,6,9,9a-hexahydro-6,9- CI 1_o methano-2,4,3-benzodioxathiepin-3-oxide 0 h CI O-S• CI

:~12CI 1,2,3,4,10,10-Hexachloro-6, 7-epoxy-1,4,4a,5,6, 7,8,8a• h octahydro-l,4-endo,endo-5,8-dimethanonaphthalene CI CI 0 ~~ EPN O-Ethyl-O-p-nitrophenyl phenylphosphorothioate ~P'ODNO'C2 H sO _

EPNO Oxon analog of EPN o II CH OCNHCH 13 A 3 Eserine 5-Methylcarbamoyloxy-1,3a,8-trimethyl-2,3,3a,8a-tetrahydr0- .~ pyrrolo-[2,3-b]-indol W -W ~ I I I CH3 CH 3 9 C2HsO S S OC2HS 11/ 3 "I P-SCH S-P [ 0,0,0' ,0' -Tetraethyl-S,S' -methylenebisphosphorodithioate /2,,- :;• C2HsO OC2 HS ~ >c

..... ~ -.J Wo

Common Name or Designation Chemical name Structure i ~ Ethyl Chlorthion O,O-Diethyl analog of Chlorthion 5" ~ >< Ethyl Dichlorvos O,O-Diethyl analog of Dichlorvos

Ethyl Guthion (See Azinphosethyl)

CH30~~ Famphur 0-[ 4-(dimethylsulfamoyl)phenyl]-0,0-dimethyl phosphorothioate CH30/ P"0 -Q-~_ S02N(CH3)2

OH FDMC 4,4' -Dichloro-cx-trifluorometh-ylbenzhydrol Cl-Q-f-Q-CI CF 3

o II Fenethcarb 3,5-Diethylphenyl methylcarbamate A HCH3 C2 H S ~ C2 Hs

S CH30~11-Q-" 0,0-Dimethyl-0-(3-methyl-4-nitrophenyl)phosphorothioate /p"O 'I '\ N0 2 CH 3 0 _

CH 3 S CHlO, II -Q-"H / p...... 0 '/ '\ SC l 0,0- Dimethyl-O-[ 4-(methylthio )-m-tolyl]phosphorothioate CHlO _

CHl

C4 H g S Folex S,S,S-Tributyl phosphorotrithioite "-p / "- C4 HgS SC4 Hg Furadan (See Carbofuran)

Gardona (See )

C-¢jQ=HlO0 OCHl Griseoful Yin 7-Chloro-4,6-dimethoxycoumaran-3-one-2-spiro-l' - ~I 0 (2' -methoxy-6' -methylcyclohex-2'-en-4' -one) CHlO::::::"... 0 CI CHl Guthion (See Azinphosmethyl)

CIACI HCH Isomers of 1,2,3,4,5,6-hexachlorocyclohexane CIVCI CI N 9 (CHlhNy irN(CHlh 3 Hemel 2,4,6-Dimethylamino-s-triazine NyN [ :;• N(CHlh ~ >c

-.oJ ~ ..... ~ Q Common Name or Designation Chemical Name Structure ~ ~ ::; l} °II )( Hempa Hexamethylphosphorictriamide (CH3hN- p- N(CH3h I N(CH3h

H N'!(ONa Heptabarbital (sodium) Sodium 5-(l-cyc1ohepten-l-yl)-5-ethylbarbiturate QX# N C2HS o

Cl 1,4,5,6,7,8,8-Heptachloro-3a,4, 7, 7a-tetrahydro-4, 7-endo- :1ka12 methanoindene h CI CI ~ CI

Hexamethonium Hexamethylene-bis(trimethylammonium bromide) [(CH3hN+[CH2J6N+(CH3hJ2Br-

CH3 I (yxN oNa Hexobarbital (sodium) Sodium 5-(l-cyc1ohexen-l-yl)-1,5-dimethylbarbiturate 1 CH3¥ ° 0 II Ethyl-3,7,II-trimethyldodeca-2,4-dienoate MJvv\; ~ ~ COC2 HS Imidan (See )

Cl~ZCl Cl exo-I-exo-3,4,5,6, 7,8,8-0ctachloro-I,3,3a,4, 7, 7a-hexahydro- Cl 0 4,7 -methanoisobenzofuran .& Cl Cl Cl

C~IZCl Isodrin 1,2,3,4,lO,lO-Hexachloro-l,4,4a,5,8,8a-hexahydro- Cl 1,4-endo,endo-5,8-dimethanonaphthalene .& Cl ....., Cl

Ch ° Isolan 1-Isopropyl-3-methyl-5-pyrazolyl dimethy1carbamate ~,~,J-II N'N OCN(CH3h I CH(CHJh

Isopropyl Diazinon O,O-Diisopropyl analog of Diazinon

Isopropyl O,O-Diisopropyl analog of Paraoxon

Kelthane (See Dicofol)

O Kepone Decachlorooctahydro-I,3,4-metheno-2H - C~CICI CI 9

cyc1obuta[c,d]pentalene-2-one CI CI ~ [ Clz CI Cl :i" ~ )(

-.J CAl CAl ..... ~

Common Name 9 ~ or Designation Chemical Name Structure c::;. ~ S" Landrin Commercial insecticide contains SD 8786 (18%) and ~ SD 8530 (75 %) )(

II Lethane 60 2-Thiocyanoethyl esters of C10-C1Baliphatic acids ° R -COCH 2CH2SCN

Lilly 18947 2-[(4,6-Dichloro-2-biphenylyl)]oxy CI OCH2CH2N(C2Hsh

CI

Lindane (See HCH, )I-isomer)

Malaoxon Oxon analog of

CH30 S ° "II II P-S-CHCOC 2H S Malathion O,O-Dimethyl-S-l,2-di(carboethoxy)ethyl phosphorodithioate / I CH30 CH2~OC2Hs o

CH 30,j =

y CH 3 CH 3 o l;ucu,II Mercaptodimethur 4-Methylthio-3,5-xylyl methylcarbamate

CH 3 ¥CH 3 SCH3

Mesurol (See Mercaptodimethur)

CH 3 \ Metaphoxide Tris(2-methyl-I-aziridinyl)phosphine oxide ( C:NtP=o

Methiocarb (See Mercaptodimethur)

Methiochlor 2,2- ~is(p-methylthiophenyl)-I,I, I-trichloroethane CH3S-o-~-o-SCH3 CCI [ CH3 0 s- I II Methyl-N -[(methylcarbamoyl)oxyJthioacetimidate ~ CH3 SC=NOCNHCH 3 :s• ~ ><

-..J W 0'1 ~

Common Name 9 ~ or Designation Chemical Name Structure [ o 5' II ~ Isopropyl-l I-methoxy-3,7,l I-trimethyl dodeca-2,4-dienoate CH30 MvJvCOCH(CH3h >< ~ ~

Methoxychlor 2,2-Bis(p-methoxyphenyl)-l,l,l-trichloroethane CH30-o-~-o-0CH3

CCl 3

Methyl Acethion O,O-Dimethyl analog of Acethion

Methyl Paraoxon Oxon analog of Methyl

CH30 S '-.11 P Methyl Parathion O,O-Dimethyl-0-4-nitrophenyl phosphorothioate CH30/ '-.0-0- N0 2

CH30 0 '-.11 0 0,0- Dimethyl-l-carbomethoxy-l-propen-2-yl phosphate /P'-. II CH30 0-C=CHCOCH 3 I CH3

~ l;HCH' Mexacarbate 4-Dimethylamino-3,5-xylyl methylcarbamate

H3CVCH 3 N(CH 3h o MGK 264 N -(2-ethylhexyl)-5-norbornene-2,3-dicarboximide ~ N-CH'rH(CH,),CH, o C2 HS

(CH3 hCHNH ° "'.11 N,N -Diisopropylphosphorodiamidic fluoride p / "'. (CH3hCHNH F

CI C12 Dodecachlorooctahydro-l,3,4-metheno-2H-cyclobuta• [c,d]pentalene Cl CI CI~ Cl CI 2 CI CI

II Mobam Benzo[b ]thien-4-yl methylcarbamate OCNHCH3° caI ?" ~I s

CH 3 0 "'.11° Monocrotophos 3-(Dimethoxyphosphinoxy)-N -methyl-cis-crotonamide P CH 0 / "'. I 3 II i CH3 0 OC=CHCNHCH 3 [ ::;• ~ ><

w" " ..... w OJ

Common Name 9 or Designation Chemical Name Structure 3 [ ::l CH 3 ~ I >< Mylone 3,5-Dimeth yl-tetrah ydro-l ,3,5,2 H -thiadiazine-2-thione (Ni SyN-CH 3 S Neopynamin (See )

/CH 2 -S\ 4-N,N -Dimethylamino-l,2- (CH3hN-C~

CH 2 -S

Nicotine 1-3( 1-Methyl-2-pyrrolid yl)pyridine l J "~/ ~N CH 3

Nornicotine 1-3-(2-Pyrrolidyl)pyridine :r-QlNJ '~/

(CH 3h 0 NRDC-108 5-Benzyl-3-furylmethyl-2,2,3,3- tetramethylcyclopropanecarboxylate »-~OCH'l)LcH,-Q (CH 3h ) 3 C-CH 0 (CH 2 - »-II jL -0Ij ~ NRDC-119 5-Benzyl-3-furylmethyl( + )-cis-chrysanthemate COCH 2 l CH2_ (CH 3 h ° OMPA (See )

o Ovex p-Chlorophenyl p-chlorobenzenesulphonate CI-o~oM-o~ CI - II - o

2-PAM Pyridine-2-aldoxime methiodide UCH=NOHN I CH 3

Paraquat 1,1'-Dimethyl-4,4'-bipyridylium ion H3C-N~N-CH3+~ ~Ij~+

Paraoxon Oxon analog of Parathion

C 2 H sO S "..Ii Parathion O,O-Diethyl-O-4-nitrophenyl phosphorothioate P [ C H O "..0 -o~ _ N0 2 2 s / ~ :s• ~ ><

.... !2l -.I ~

Common Name or Designation Chemical name Structure i [ :;• CI CI ~ " PCP Pentachlorophenol CI{>OH

CI CI

CH 3 0 ~ Pentobarbital (sodium) Sodium 5-ethyl-5-(I-methylbutyl) barbiturate C H _I !;yONa 3 7 CH II C H N 2 5 o

CI

,/"C=CH 0II -Q~ (3-Phenoxybenzyl)-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate COCH CI (ct-, - 0-0

H ~INrONa Phenobarbital Sodium 5-ethyl-5-phenyl barbiturate (sodium) '={2H~ o o o-D( CH 2,.,CH] Phenylbutazone 1,2-Diphenyl-3,5-dioxo-4-n-butylpyrazolidin 6° Phenytoin (See Diphenylhydantoin, sodium)

C2 H sO S "II O,O-Diethyl-S-[(ethylthio)methyl]phosphorodithioate P C 2 H sO / "SCH 2SC2 Hs

C2HSO,,~:c 0,0-Diethyl-S-[(6-chlorobenzoxazalone-3-yl)methyl]• H /" H-N 0 2 phosphorodithioate 2 SC I I /. C S ?--... // CI o 0

Phosdrin (See Mevinphos)

CH30,-~'- 0ce 7" I CH 3 0 SSCH 2 N Phosmet O,O-Dimethyl-S-phthalimidomethyl phosphorodithioate /' ~ o CH3 0 0 Q "II P CH 0 ~ 0-2-Chloro-2-diethylcarbamoyl-l-methyl vinyl-O ,0- / " I 3 II [ dimethyl phosphate CH30 OC=C-CN(C 2 Hs)2 I ::;• CI ~ ><

-.J ~ -....I il:)

Common Name 9 ~ or Designation Chemical Name Structure [ :l C2 HsO S ~ Phenylglyoxylonitrile oxime-O,O-diethyl phosphate "IIP >< C2HsO/ "O-N=C ~ CNI~ Phthalthrin (See Tetramethrin)

0yYC 3 H7 Piperonyl but oxide 3,4-Methylenedioxy-6-propylbenzyl n-butyl diethyleneglycol ether

.~II Procaine (HCI) p-Amino-N -(2-diethylaminoethyl)benzamide hydrochloride H2N~ °CONHCH 2CH2N(C2Hsh' HCI

II OCNHCH° 3 Propoxur 2-Isopropoxyphenyl methylcarbamate o-OCH(CH,),

II °COCH 2CH2CH 3 Propyl isome Di-n-propyl-6, 7-methylenedioxy- 3-methyl-l,2,3,4- tetrahydronaphthalene-l,2-dicarboxylate

(CH'hC=C~. ~ CH,

Pyrethrin I Pyrethrolone ester of chrysanthemic acid rCO~ CH 2CH=CHCH=CH 2 (CH')2 Y o HC '''C=CH 0 CH ~ II , II Pyrethrolone ester of pyrethric acid CH,of rCO~CH,CH~CHCH~CH, (CH,h Y o Dried flowers of Chrysanthemum cinerariaefolium containing several insecticidal components (See , II)

Rabon (See Tetrachlorvinphos)

o S CI CH, "II -0- Ronnel O,O-Dimethyl-O-2,4,5-trichlorophenyl phosphorothioate /p" f ~ CI CH 3 0 o _

CI

CH3NH,,~CI RueIene 0-4-tert-Butyl-2-chlorophenyl-O-methyl i methylphosphoramidate C(CH /p "0 h 3 h [ CH 3 0 --v- :;• ~ ><

'-I ~ -.,j t

Common Name or Designation Chemical Name Structure i [ Ryania Insecticidal material from ground stem wood of various ::;- Ryania species. Contains several alkaloids including ),; *

Sabadilla Insecticidal material from seeds of sabadilla (Schoenocaulon officinale Gray). Contains several veratrine and cevadine alkaloids.

(CH 3hCHO 0 Sarin O-Isopropyl methylphosphorofluoridate "IIp

CH3 / "F

SBP-1382 Mixture of Bioresmethrin and NRDC-119

(CH 3hN 0 0 N(CH 3h 11/ Schradan Octamethylpyrophosphoramide "IIP-O-p

(CH 3hN / "N(CH 3 h

o II l;HCH' SD 8530 3,4,5-Trimethylphenyl methy1carbamate

H3CYCH 3 CH 3 o II OCNHCH3 SO 8786 2,3,5-Trimethylphenyl methylcarbamate ACH 3

H3C~CH3

II oCNHCH3° SO 9003 2,4,5-Trimethylphenyl methylcarbamate (r?" CH 3 H :::,....1 3C CH 3

CH30 "II° SO 11319 3-(Oimethoxyphosphinoxy)-cis-crotonamide P CH 0 /" I 3 II CH30 OC=CHCNH 2

H o N Seconal (sodium) Sodium 5-allyl-5-(I-methylbutyl- barbiturate CH2=CHCH2I;\(ONa C3H 7 CH N I CH 3 0 9 0TH(OCH2CH2hOC2Hs 2-(3,4-Methylenedioxyphenoxy)-3,6,9-trioxaundecane <

....a ~ (11 ...... ~ 9 Common Name 3 or Designation Chemical Name Structure [ Cl :l ~ >< Simazine 2-Chloro-4,6-bisethylamino-l,3,5-triazine NAN ~Jl C2HSHN N NHC2Hs n SKF-525A 2-(Diethylamino)ethyl-2,2-diphenylpentanoate yo ~ C-~O(CH2)2N(C2Hs)z o-- I CJ H7

CH 0 3 "-f' So man 0-1,2,2-Trimethylpropyl methylphosphonofluoridate p H / " (CH 3hCCO F I CH3

Stauffer R 20458 1-(4' -Ethyl phenoxy)-6, 7-epoxy-3, 7-dimethyl-2-octene ~0-o-C2HS

Stirofos (See Tetrachlorvinphos)

Strobane Mixture of polychlorinated terpenes C2HsO S S OC2HS "II 11/ Sulfotep Bis-O,O-diethylphosphorothionic anhydride P-O-p C2HSO / "OC 2Hs o II oyy CH2CHS(CH2hCH 3 Sulfoxide 1,2-Methylenedioxy-4-[2-( octylsulfinyl)propylJbenzene <0--0 tH3

Sumioxon Oxon analog of Fenitrothion

Sumithion (See Fenitrothion)

C2 H sO S "IIp SV1 0,0- Diethyl-O-phenyl phosphorothioate C2 HsO/"0-0

Systox (See Demeton; commercial product contains 65 % thiono and 35 % thiolo isomers)

C2HsO 0 Tabun O-Ethyl dimethylphosphoramidocyanidate "IIp (CH3)2N / "CN Q TBTP (See Folex) ~ TDE (See DDD) [ :;• ~ "" -..j ~ ~

Common Name Q or Designation Chemical Name Structure ~ ~ :l I'N N N~ ~ Tern 2,4,6-Tris( l-aziridinyl)-s-triazine YIr '" NyN N L:::,.

Temik (See Aldicarb)

Tepa Tris( l-aziridinyl)phosphine oxide (tNt-P=O

C2H 5 0 0 0 OC2H 5 TEPP Diethylphosphoric anhydride "'-IIP-O-P 1\/ / "'- C2H 5 0 OC2H 5

Cl Tetrachlorvinphos 0-2-Chloro-l-(2,4,5-trichlorophenyl)vinyl-0 ,O-dimethyl CH 3 00 12r phosphate "'-~-O-CIj ~ Cl / 11_ CH 30 HCCI Cl Tetram Oxalate salt of Amiton o (CH 3 hC=CH 0 ~ Tetramethrin N -Hydroxymethyltetrahydrophthalimide ( + )-trans-chrysanthemate }>-~OCH2-N~

(CH 3)2 0 ~OCCH SCN Thanite Isobornyl thiocyanoacetate C(CH)h ~ 2

Thiotepa Tris( l-aziridinyl)phosphine sulfide ([:Nt-P=S

CH) Tirpate 2,4-Dimethyl-l,3-dithiolane-2-carboxaldehyde-O- h (methylcarbamoyl)oxime S Sx ~ H)C CH=NOCNHCH)

TOCP (See TOTP) o 0 N N' H C SHN-CNHCII H Tolbutamide -p-tolylsulfonyl- -n-butylurea ) Oil _ II 4 9 0

TOTP Tri-o-tolyl phosphate (Q-0-)"~o CH) )

Toxaphene Chlorinated camphene (67-69% chlorine). Insecticidal CH CIs -E): 2 mixture consists of complex mixture of isomers (CH)h 9 ~ ~. TPP O,O,O-Triphenyl phosphate (O-O+~O -::; It,.

..... ~ ..... g:

Common Name 9 or Designation Chemical name Structure 3 ~ S• CH 3 0 0 l} "-,f' >< Trichlorfon O,O-Dimethyl-(1-hydroxy-2,2,2-trichloroethyl)phosphonate P CH30 / "9H-CCI3 OH

Trithion (See Carbophenothion)

O(CH2CH20hC 4H 9 / Tropital Piperonal bis[2-(2-butoxyethoxy)ethyIJacetal O~CH <0--0 "O(CH 2CH 20)2C4H9 o II UC 10854 3-Isopropylphenyl methylcarbamate A HCH3 V CH(CH 3)2

S Vapam Sodium methyldithiocarbamate II CH3NHCS. Na

o

Warf anti resistant N,N-Di-n-butyl-p-chlorobenzenesulfonamide ~ MN(C4H9h CI -o-11 - 0

Zectran (See Mexacarbate) C2 HsO S "IIp Zinophos 0,0- Diethyl-O-2-pyrazinyl phosphorothioate / " N C 2 HsO °1) N ZR-SlS (See Methoprene)

~ :3 [ :l ~ ><

-.J ~ Index

Abate, 99,438,457,473,481 Action potential, 328, 331, see also Nerve Absorption of insecticide, 3-58,448-459,607- action potential, Nerve membrane 609 Activity, intrinsic, 255 see also Penetration and Insecticides, distribu- Acyrthosiphon pisum, 488,489 tion and penetration Adenosine diphosphate (ADP), 367-372, , 473 381, 382, see also Phosphorylation, Acethion, 156,468 oxidative, and Respiration 2-Acetylaminofluorene, 185,214, 215 Adenosine triphosphate (ATP), 367, 369, , 251, 252, 256, 260, 272,292, 382, 384, see also Phosphorylation, 297-326,419 oxidative, and Respiration antagonism in therapy, 292-293, 658 in phosphate conjugation, 184 hydrolysis, see Adipose tissue and insecticide storage, 40-42, receptor. 297-326 613,614, see also Insecticides, dis• identification, 302-308 tribution insecticide interactions, 314-319 ADP, see Adenosine diphosphate purification and properties, 309-314 Adrenodoxin, 70 reaction with anticholinesterases, 317-319 Adsorption of insecticide, 694-695 transmitter action, 248-253 Aedesaegypti,384,438,481,488,489,519 Acetylcholinesterase, 20, 27,52,271-296, Aflatoxin, carcinogenic action, 560 400,402-407,410-413,471,477- Ageratum horstonianum, 491 484,493,511-516,624-626,629,657 Agonists, defmed, 255, 300-301 aging of phosphorylated, 291 -receptor complex, 255-256 altered in resistance, 511-516 Albumin, insecticide binding in blood, 21,609 and selective toxicity, 477-484 Aldicarb, 82, 99, 101,660 as a target, 274-276 Aldrin, 230, 346,347,438,533,534,574- biology and properties, 271-274 576,614,621-627,683,696 inhibition metabolism, 85 by , 289-290 trans-diol, 230, 345-348 by , 286-289 Aliesterase, 156-161 nature and kinetics, 276-281 inhibition by phosphates, 158,628,629 isozymes, 273-274 mutant in resistance, 530, 531 sites on active surface, 281-286, 477-479 properties, 156-161 allosteric, 286 see also Carboxylesterase, Esterase, Hydro• anionic, 282 lase catalytic, 281-282 Allethrin, 89,102,160,207,230,231,336- hydrophobic, 282-283 338 indophenyl binding, 285 4-Allylbenzyl-cis-trans-chrysan thema te, 44- 46 Acetyl-coenzyme A acetyltransferase, 184 Almond moth, see Cadra Actinomycin D, 615 Alodan,472 753 754 Index

Alternative substrate inhibition, 534 1,2,3-Benzothiadiazole, synergists (cont'd) Amanita phalloides poisoning, 653 structure vs. activity, 424 Amidase, 162-164,468,469,629, see also see also Synergist Carboxylamidase Benzylthiocyanate, 632, see Organothio• Aminocarb, 84, 101 cyanates Aminopyrine, 617 Benzpyrene, 135, 137,560 Amiton, 28, 30, 289,292 hydroxylase, 79 Amy tal, 374 BHC, see -y-HCH , 419, 420, 663 Bidrin, 164,585,586,630 Antagonist, defined, 300, 301 Binding spectra types, 124, 125, 138, 141, Antijuvenile hormone, 491 see also Cytochrome P450 Antimycin A, 373-376, 380 Biomagnification,612 Antipyrine, 617 of insecticide residue, 684-686 Aonidiella aurantii, 381 in aquatic animal, 685-686 Aphid, see Myzus in food chain, 684-685 Apholate,589-591 and toxicology, 684-686 Apis mellifera, 19, 357, 388 Biotransformation, 3942, 321,610-611 Arene oxide, 92, 94, see also Epoxide of insecticide, 687-699 Arylester hydrolase, 151-154 chemical, 696-699 of insects, 153-154 metabolic, 690-691 of mammals, 151-153 microbiological, 688-690 Arylpropynyl ether, synergist, 127, 632 photochemical, 691-693 Ascaris lumbricoides, 473 physical, 693-696 Aspon,496 Bird egg and insecticide, 26 ATP, see Adenosine triphosphate Blaberus cranifer, 456 Atrazine,698 B. sp.,461 Atropine, 292, 293,658-661 Black Leaf40, 664, see Nicotine antagonizing effect, 345 Black widow spider venom, 229, 251 in organophosphorus poisoning, 658-661 Blastomogen,557 Axomyelin degeneration, delayed, 264 Blatella germanica, 11,161,384 Axon, 257 Block, depolarizing, in synaptic transmission, Axonic transmission, 233-248, 328-329, 253, see also Nerve membrane see also Nerve membrane, Nervous Blood, see Absorption, Insecticide distribu- system, Neuromuscular junction tion, Penetration , 230 and bile in excretion, 22 Azinphosmethyl, 439, 440, 533, 537 and brain, barrier, 27, 263,457458 Azodrin, 164,585,586,630 as transport medium, 21,609 Blowfly, see Calliphora, Lucilia, Phormia Banol, 84, 101,636 Body louse, see Louse Barbiturate, 25,614,616 Bombyx mori, 365 Barrier concept, 6, 27, see also Penetration Bond, hydrophobic, 283 and Insecticides, distribution and Boophilus microplus, 513, 514 penetration altered cholinesterase in, 514 Batrachotoxin, 229,258 Botanicals, 206-212 1,3-Benzodioxole, synergists, 127,422,632, Botulinus toxin, 229, 231 see also Methylenedioxyphenyl com• Bracon hebetor, 591 pound, Synergist f3-Bungarotoxin, 251, 303 structure vs. activity, 422424 Butacarb, 84, 441, 495 substituent effect, 424 Butyrylcholine, 272,477 synergist, 422424 Butyrylcholinesterase, 271, 283 1,4-Benzoquinone, respiratory bypass, 388 diethyl phosphoryl-, 291 1,2,3-Benzothiadiazole, synergists, 127,424, diethylphosphoryl-, recovery from inhibi• 632 tion,291 Index 755

Cabbage looper, see Trichoplusia ni Cartap, 316 Cable theory, 243-245 Cattle tick, see Boophilus of cable properties of nerve, 244 Central nervous system (CNS), 27, 258, 262, Cadra sp., 380 see also Nervous system Caffeine, 582 differences between insects and mammals, California red scale, see Honidiella 262-264 Calliphora erythrocephala, 167, 185,204 Cevadine, effect on negative after potential, C. vomitoria, 357,359 259 Cancer, defined, 557, see also Carcinogenesis Charcoal, activated, as antidote, 616 Capacitance, 244, see also Farads Charge-transfer complex Carbamate, 47, 50, 51, 84,96,102,166-167, in acetylcholinesterase inhibition, 283- 285 196-198,231,274,277,313,409- in action of DDT, 415 413,437,472,479,480,512,536, Chemosterilant, 589-591 538 Chitin, 6, 8 conjugates formed in metabolism, 199-201 Chlorcyclizine, 622, 626 inhibition of acetylcholinesterase, 289, Chlordane, 135, 136,574,615-618,621, see also Acetylcholinesterase 627,636,677, see also Cyclodiene interaction with cytochrome P-450, 125 insecticides microsomal oxidation, 79-99 Chlordimeform, 84, 438 poisoning, treatment of, 660-661 , 11, 82, 100,438,439,461, resistance to, 538-540 492 structure-activity relationships, 409-413 Chlorinated insecticide in animal fat, 40-42, Carbamylation rate, 289-290 612-616, see also Hydrocarbon, Carbanion, theory of synergistic action, 133, chlorina ted see also Synergism, Synergist 5-Chloro-2' -chloro-4' -nitrosalicylanidile, 383 Carbaryl, 20, 21,50,51,61,99,101,136, p-Chloromercuribenzoate,301 166,170,202,214,281,422,436, 3-Chloroperbenzoic acid, 96 437,439,451,452,456,467,533, Chlorophos, 584 539,541,587~89,677,691 Chlorphenothane, 661, see also DDT Carbofuran, 90, 482, 660,691 Chlorpromazine, 99 Carbon monoxide, 74, 75, 97,117,119, Chlorthion, 101,631 128, 138, see also Cytochrome P-450 Choline acetylase, as a target, 486 Carboxylarnidase, 162,629, see also Amidase, Cholinergic junction, 259-262, 297-301 Esterase, Hydrolase Chrysomya putoria, 527-531 in interactions, 629 Chymotrypsin, 283 in selective toxicity, 468 Cicada, see Magicicada properties and inhibition of, 162-164 Cimex lectularius, 527,531 Carboxylesterase, 156-158,468,469,526- Cinnamic acid, 389 529,628,629 Cleft, synaptic, 250-253 and selective toxicity, 468, 469 Cobra, neurotoxic venom, 229, 309 in resistance, 527-531 Co carcinogenicity , 633 interactions through inhibition of, 628,629 Cockroach, see Blattella, Periplaneta metabolism of organophosphorus com- Madagascar-, 166,167, 184, 185 pounds, 156-158 Codistillation, 694 metabolism of , 160-161 Coenzyme Q, 366, 373, 378, 388 properties and inhibition of, 156-158 Colombian poison arrow frog, 229, 258 Carcinogen, 557,558,561 Colorado potato beetle, see Leptinotarsa Carcinogenesis, chemical, 214 Compartmental analysis in pharmacoki- defined,556,557 netics, 35-39, see also Insecticides, Carcinogenicity penetration defined, 556 models used in, 35 tests, 566-567 Concentration gradient across membrane, 40, Carnitine, 359 see also Absorption, Penetration 756 Ind(Jx

Condensation reaction, microbial Cytochrome c, 363, 364, 373 of insecticide, 690 NADPH reductase in micro somes, 66-67,116 Conductance, 238,239,246 oxidase, 373 Conductance, ionic, 298 inhibitors, 380-381 Conduction, saltatory, 263 Cytochrome P420, 68, 69,117,121 Conine poisoning, 664 Cytochrome P450, 66, 68-79, 97, 103, 115- Conjugation, biochemical, 177-225 148,541,611 and insecticide metabolism, 186-212 in microsomal electron transport, 67-69,122 of botanicals, 207 in resistance, 140-142 of carbamates, 196-198 induction, 71, 122-124 of chlorinated hydrocarbons, 198-206 in insects, 137-139 of insect hormones, 208-212 in mammals, 135-137 of organophosphorus compounds, 187-196 interactions, 115-148 of organothiocyanates, 207, 208 with insecticides, 124-127 with glucose, 180-182 with synergists, 128-131 with glucuronic acid, 179-180 methodology for studying, 116-121 with glutathione, 183, 184 substrate binding spectra, 117-120 in resistance, 532-533 see also Microsomal mixed-function oxidases with glycine, 185 Cytochrome system, 361-366 with phosphate, 184, 185, 1811-196 microsomal, 66-72, see also Cytochrome with sulfate, 182-183 P450 and Microsomal mixed-function Conoderus vespertinus, 432 oxidases Co-Ral,623 mitochondrial,361-366 Coroxon, 483,484, 513,514 inhibition of, 373-381 Cotinine, 432 Coumaphos, 514, 634 2,4-D,693 Cross resistance DDE, 25,457,521,615,616 dermed,511 DDT, 8-13,15,16,25,31,33,36,41,47, negatively correlated, 543 48,52,85,94,125,135-138,150, to insect hormones, 540 152,204-206,230,231,243,247, see also Insecticide resistance 248,258,259,330-337,383-386, Culex pipiens fatigans, 409, 410, 538, 539 413-418,437,446,449-452,457, Culex tarsalis, 527-531 461,468,485,510,516,517,521, Current, capacitive, 244 522,524,535,536,567-575,612- Cushing's syndrome, 619 619,624,627,634,636,637,649, Cuticle of insect, 6-12 651,661,671,672,675,678,683, penetration through, 6-12, 448-457 686,688,696 see also Absorption, Penetration effect on nerve transmission, 330-336 Cyanide interactions, 613-619 detoxication, 186 affecting tissue storage, 613-619 inhibition of cytochrome c oxidase, 380 with organophosphorus compounds, 622- insensitivity of millipedes to, 432, 485 627 resistance to, 381 metabolism, 205-206,521-524, see also Cycling, enterohepatic, 22,616 DDT -dehydrochlorinase Cyclodiene insecticides, 22, 51, 85, 87, 168, Mullins' model of receptor site for, 413-415 345-348,485,518,574-577,612,637 outlawed in U.S.A. (1972),683 effect on nerve transmission, 345-348 poisoning in man, 661-663 metabolism, 84-89 resistance to, 516-524, 535-537 resistance to, 518 substituent effects on toxicity of, 415-418 terotogenic, mutagenic, and carcinogenic teratogenic, mutagenic, and carcinogenic effects, 574-577 effects, 567-574 Cytisine poisoning, 664 DDTase, see DDT -dehydrochlorinase Cytochrome bs' 66, 68, 70, 74, 116, 122 DDT-dehydrochlorinase, 205-206,510,516, reductase in microsomes, 70, 116 517,521-524,535-537 Index 757

DDT -dehydrochlorinase (cont'd) Diazoxon, 42, 43, 96, 153, 194, 195,461, properties of, 205-206 471,472,514,525,526,532,537 DDVP,513, 155, see also Dichlorvos Dichlorfon,581 mutagenic effects, 582-585 5,6-Dichiorobenzothiadiazole synergist, 130, Dealkylation, 80-84,155,188-195,291-292, 135 532 2,6-Dichlorophenolindophenol, 388 glutathione dependent, 188-195 Dichiorvos, 581-585, see also DDVP in resistance, 532 Dicrotophos, 83, 102,622,623 hydrolytic, 155 Dieldrin, 9-14, 20-26,30-33,36,41,47,85- in aging of phosphorylated acetylcholineste• 88,138,169,230,345,346,435- rase, 291-292 438,451,452,457,461,464,468, microsomal, 80-84 510,518,533,574-576,612-616, see also Conjugation, Esterase, Hydrolase, 627,636,661,674,683-686,692,694. Microsomal mixed-function oxidase 698, see also Cyc10diene insecticides Dearylation, glutathione dependent, 195-196 Difference spectroscopy, 118, see also Cyto• in resistance, 532 chrome P450, Microsomal mixed-func• Decamethonium, 231, 286 tion oxidases Decay constant, in pharmacokinetics, 39 Diffusion, 35, see also Absorption, Penetra- Dehalogenation, microbiological, 688, 698 tion, Membrane penetration Dehydrogenases in respiration, 354-366 facilitated, 6 flavin-linked, 365 passive, 6, 23 a-glycerophosphate, 356-358 pressure, 235 isocitric, 360-361 6,7-Dihydroaldrin, 48, 50, 89 malic, 361 6' ,7' -Dihydr0-6',7' -dihydroxyrotenone, 91 NAD-linked, 360 p-Dihydroheptachlor,472 see also Respiration 6,7-Dihydroxydihydroaldrin, 32, 85 Deisopropyl parathion formation, 82 neuroactive effects, 230, 345-348 Delnav,633 Dimethoate, 12-15,20,21,47,48,50,83, Demeton, 99, 586, 587 162,164,441,451,456,468,470, N-Demethylation, 84, 131, see also Dealkyla- 473,514,581,623,629,630,634 tion Dimethoxon, 288,470, 630 Demethylcotinine, 84 Dimethrin, 91 Dendrites, 257 2,6-Dimethyl-4-allylbenzyl-(± )

DT-diaphorase, 389 Ethion, 623, 702 Dyfonate, 96 Ethionine, 615 Dysdercus cingulatus, 488 Ethyl acethion, 528 Ethylene glycol, 653 Ecdysone, 76,491 S-Ethylglutathione, 194 Edrophonium, 317, 319 Ethyl guthion, 634 Ehrlich's notion of receptor, 299 Ethyl isocyanide, 120 Electric eel, see Electrophorus electricus Ethylmorphine difference spectrum, 131 Electric ray, 304 Ethylparaoxon, 464, 465, see also Paraoxon Electrogenesis, 238,258-259 Ethyl parathion, 481 ,493,see also Parathion Electrophorus electricus, 303, 304 Excision assay, 450 E. electroplax, 310,313,317 Excitability of nerve, 237 Electrophysiological approach, 330 Excretion, 21-25,462 Endoplasmic reticulum, see Reticulum, Micro• some F AD, see Flavin adenine dinucleotide Endplate False hellebore, see Veratrum current, 342 Famphur,83 dose-response curve, 342 Farad,244 membrane, 253, 340 Farm worker potentials, 253, 341, 346 exposure to insecticide, 700,705 Endrin,12,22,87,468,575,576,661,see route of entry, dermal, 705 also Cyclodiene insecticides oral,705 Energy transfer system, 367, 384-387 respiratory, 705 inhibitors, 384-385 field reentry safety interval, 703 see also Oxidative phosphorylation, Respira- protection, 704 tion Fatty acid oxidation energy source in insects, Environmental Protection Agency (EPA), 681 359 EPN, 164,585-587, 622, 623, 630 Federal Environmental Control Epoxidation, 84-91, see also Microsomal mixed- Act(1972),681 function oxidases Federal Environmental Protection Agency, 681 Epoxide Federal Insecticide, Fungicide and Roden- formation, epoxidase, 84-91, 100,.464, see ticide Act(1972), 681 also Epoxidation Fenitrothion, 479 hydration by hydrases, 85, 94, 167-171, Fenthion, 441, 586-587 464-465 FEPCA, see Federal Environmental Pesticide mechanism, 168 Control Act transferases, 184 Fick's law of diffusion, 13 Equilibrium dialysis, use of, 302-304 Filipin, 491 Equilibrium potential, 234, see Nernst equa• Fire ant, see Mirex tion Fish, electric organ, 304 Escherichia coli, 582,590 Flavin adenine dinucleotide(FAD), 97 Ester oxidation, 94-96, see also Microsomal Fluenethyl selectivity, 474,475 mixed-function oxidases Fluorene, 133 Esterases Fluoroacetate, 385,475 A-esterase, 151,464-465,472,625 and derivatives, selectivity of, 474-475 B-esterase, 151, 156, 158,625,627,628 mode of action, 385 in carbamate metabolism, 166 Flux, ionic, 238 in metabolism, 149-160, Folex,623 162-164,525-531,620-621 in metabolism, 160-161 Gallamine, effect on carbamylation, 286 in resistance,S 25 -5 31 Galleria mellonella, 371,488 in selective toxicity, 468-469 Gardona, 82, 441 see also Acetylcholinesterase, Aliesterase, Gastric juice, pH and penetration, 17 Amidase, Carboxylesterase, Hydrolase Gate protein, 298, see also Ionic gates Index 759

Gene kdr (knockdown resistance), 516-517 Heliothis virescens, 12, 33,488,542 Generator potential, sensory cell response, Hellebore, 663 237 Hemel,591 Glossina, see Tse tse fly Hemicholinium,261 GSH-S-alkyltransferase, 194-196, 205-206, Hemolymph, 12,53 see also Conjugation;Glutathione Hempa,491 conjugation Henderson-Hasselbalch equation, 17 Glucose conjugation, 180-182 HEOD, 38-40, see also Dieldrin, Cyclodiene and glucosyltransferase, 181 insecticides mechanism, 180-181 HEOM, 169, 170,465 see also Conjugation Heptachlor, 575-577, 613 Glucuronic acid conjugation, 179-180 Heptachlorane,575 and glucuronyltransferase, 179 -y-Hexachlorocyclohexane, 9,13,15,31,32, mechanism, 179 135,169,198,205,229,383,485, see also Conjugation 518,579,621,636,694 L-Glutamate as insect transmitter, 260, 377 metabolism, 198 Glutamine conjugation, 177 resistance to, 518 -y-Glutamyltransferase in glutathione con- teratogenic, mutagenic, and carcinogenic ef- jugation, 184 fects, 578-579 Glutathionase, see -y-Glutamyltransferase Hexamethonium, 260 Glutathione S-alkyltransferase, 82, 150, 380, Hexobarbital, 631, 633, 635 464,465,526,532,533,621, see also Hippuric acid, 177 Glutathione conjugation HMPA,83 Glutathione conjugation, 183-184, 188-196 Hodgkin-Huxley equation, 338 dealkylation, 188 Hodgkin-Huxley membrane model, 232 dearylation, 195-196 of squid giant axon, 233 in chlorinated hydrocarbon metabolism, Holding potential, 246 204-206 Hormone, juvenile, analog of, 138 in organophosphate metabolism, 188-195 Housefly, see Musca domestica in organothiocyanate metabolism, 207-208 Hyalophora cecropia, 540 in resistance, 532 Hydrocarbon, chlorinated, 567-577 see also Conjugation, Dealkylation poisoning, treatment for, 661-663 O!-Glycerophosphate, 354-358, 364, 366,376 symptoms of poisoning, 662 shuttle inhibited, 389-390 teratogenic and carcinogenic effects, 567- O!-Glycerophosphate dehydrogenase, 356, 579 357,389 Hydrocarbon, polycyclic aromatic, 135 Glycine conjugation, 185-186 hydroxylase, 78-79 Glycolysis, 355 Hydrogen cyanide, see Cyanide Goldman constant field equation, 236 Hydrolase, 149-176 Green rice leafhopper, see Nephotettix in organophosphate metabolism, 149-160, Gromphadorhina portentosa, 273, see also 162-164,620-621 Madagascar cockroach amidase, 162-164 Gut penetration in rat, 18, see also Absorption, alkyl, 155 Penetration arylester,151-154 Guthion, 622, 623,634, 657, 677, 702 carboxylesterase, 156-160 Guthoxon,31.9 fluoro-, 150-151 phosphodiester,155 phosphotriester, 149 Habrobracon, 590 types of reactions, 150 Halobenzene, 94 in pyrethroid metabolism, 160-161 Haloxon, 465, 483, 484 in resistance, 524-5 31 Hammett's a constant, 398-399 see also Acetylcholinesterase, Aliesterase, Hammett's equation, 398-400 Amidase, Carboxylesterase, Esterase -y-HCH, see -y-Hexachlorocyclohexane Hydroprene, 138 760 Index

Hydroxycarbofuran, 90 Insecticides, distribution (cont'd) Hydroxydiazinon, 85 in tissues, 41 Hydroxylamine, 291 in vertebrates, 35-42 Hydroxylation, 62, see also Microsomal dynamics, 4, 448 mixed-function oxidases effects aliphatic, 84-91, 99 carcinogenic, 555-603 aromatic, 91-94 definition of terms, 556-557 N-Hydroxymethyl carbamate, 83, 198 mutagenic, 555-603 N-Hydroxymethyl schradan, 82 on acetylcholine receptor, 314-320 5' -Hydroxynicotine, 84 on acetylcholinesterase, 271-296 Hyperbilirubinemia and DDT, 619 on nerve transmission and conduction, Hyperpolarization, 239 327-352 on respiration, 372-390 Imidan,691 teratogenic, 555-603 Imidazole, synergists, 130, 632 entry, mode of, 5-33 Indophenyl acetate, 285, 286, see also rate of, 29,42-52,450-457 Acetylcholinesterase equilibria which influence, 52 binding site, 285-286 in estuarine water, 678 Induction, microsomal excretion, 22, 24, 42, 462 and interactions, 611, 615, 616-618 in fat, 40-42, 612-616 and resistance, 537 in food, 677 cytochrome P450, 122-124,135-139 Hammett's a constant, 398-399 mixed-function oxidases, 70-71 Hammett's equation, 398,400 see also Microsomal mixed-function oxidases interactions, 605-647 Insect absorption, 607-609 acetylcholinesterase, 273-274 biotransformation, 610-611 circulatory system and penetration, 33 distribution, 609-610 cuticle, see Integument fat storage, 613-616 fat body, 24 nutritional, 635-637 flight energy, 359 sites, 606-612 growth regulators, 486-490 synergist, 631-635 hemolymph, 5, 21 target site, 611-612 hormones 168-170, 208-212, 486-489 laws, 681 integument and penetration, 6-12, 448-450 metabolism nervous system, 9, 262-264 and selective toxicity, 462-476 respiratory system biochemistry, 354-372 conjugation, 177-225 unexploited targets, 490-491 extramicrosomal,149-176 wing beat, 354 microsomal, 61-114 Insecticides molting hormones, 212 absorption rate, 3-58,448-449,607-609, partition coefficient, 8 see also distribution, penetra tion in ovary of bird, 24 activation, 463,473-476 penetration, 3-58,448-459 as selective force, 473-476 effect of application method, 10, 50-51 amounts used in the U.S.A., 676 gut, 16-20 in California, 677 integumental, 6-12, 448-457 in atmosphere, 671-672 internal barriers, 26-33,457-462 contact speed of action, 11 kinetics, 12-16 cycling in environment, 675 mechanism, 6-12 disposal problem, 673-674 methodology for studying, 6-12, 450-452 distribution, 3-58,448-459 nervous system, 26-33 across blood-brain barrier, 30 pharmacokinetics, 52 compartmental analysis, 35-39 physico-chemical parameters, 397-428 in human fat, 40-42 poisoning of man, 649-667 in insects, 42-52 treatments, 652 Index 761

Insecticides (cont'd) l-Isopropyl-3-methyl-5-pyrazolyl dimethyl• regulations, 681 carbamate, see Iso Ian residue secretion in milk, 24 Isopropylparathion, 82, 473, 481 resistance to, 507-553 3-lsopropylphenyl-N-methylcarbamate, 47, acquired, 507-508 48,51 biochemistry, 507-553 Isosafole, 136, 137 causes, 511-543 as a preadaptive phenomenon, 508 JHA, see Juvenile hormone analog altered site of action, 511-518 Juvenile hormone, 208-212 enzymes, 518-541 metabolism, 169-170 increased metabolism, 518-541 Juvenile hormone analog reduced penetration, 542-543 conjugation, 208-212 cross-,511 cross resistance to, 540 defined,507-508 selectivity of, 437,486-489 degree of, 508-509 defined, 508 Kangaroo rat, 569 enzymes, 509-510 Kepone, 579 genetics, 509-510 Khapra beetle, 462 monogenic, 510 Kidney, mammalian, 23 multiple, 511 Kinetics penetration rate, 509 of acetylcholinesterase inhibition, 276-281 physiology, 507-553 of penetration, 12-16 polygenic, 510 Klebsiella pneumoniae, 582 selectivity, 431-506 Klein's ketone, 22, 88 spectral binding to mouse liver microsome, Knockdown resistance gene, kdr, 516-517, 124 see also Insecticide resistance stm cture( chemical}-activity correlations, 402-424 Laodelphas strilztellus, 531 synergism, 127-135,206,422-424,631-635 Lasioderma se"icorne, 432 transfer within organism, 16-33 Lavage therapy, 652 through internal membranes, 16-33 Leptinotarsa decemlineata, 360 excretory, 21-25,462 "Lethal synthesis," 385 intestinal, 16-20 Lethane, 373, 380 nervous system, 26-33 Lilly, 18947, 127,632 placental, 25-26 , see -y-Hexachlorocyc1ohexane in waste, industrial, 672 Lipophilicity, 8, 20, 77, see also Physico- municipal,673 chemical parameters in water, natural, 672· Locust, see Locusta see individual insecticides and classes of Locusta migratoria, 273,359,363,364 insecticides Lonchocarpus sp., 664 Integument, 6-12 Lucilia cuprina, 515 penetration through, 6-16, 448-457 L. sericata, 354 Ion Lumbriconereis heteropoda, 343 channels, 298, 328 Lumbricus te"estris, 78 diffusion through membrane, 235 Lygus, 461 prediction by Donnan's equilibrium, 236 gates, 298, 328 Madagascar cockroach, 166, 167, 184, 185 pump, 237, 242 Magicicada septendecim, 358 energy required, 235 Main-Iverson method, 279 Ionization degree, 17 , 20, 82, 96,159,274,275,470, Ionophere, 298 512,526,528,538,580~81,624, Ipecac, 652 625,628 Isobenzan, 21 Malathion, 14, 20, 95, 156-159, 380,438, Isolan, 11,50 450-453,468,469,512,527-531, 762 Index

Malathion (cant'd) Microsomal mixed-function oxidases (cont'd) 538,579,622,623,628-631,637, substrate binding, 73, 116-121 657,677,697 components, 66-70 Malpighian tubules in hindgut of insect, 24 cytochrome bs, 70, 116 Mammillary model, 36-37 cytochrome P450, 67-69 Manduca sexta, 21,181,185,432 NADPH cytochrome c reductase, 66-67 Mealworm, see Tenebrio moUtor dynamics, 70-72 Medullation, 263 induction, 71,122-124,135-139,537,611, Melanoplus differentialis, 432 615-618 Membrane, 6, 457-459 inhibition excretory, transfer through, 21-22 by carbon disulfide, 611 lipoprotein as barrier, 458-459 by , 611 penetration by drugs, 6 by synergists, 127-135,632,634-635 placental, 25-26 reaction patterns, 99-100 see also Absorption, Nerve membrane, reaction types Penetra tion aliphatic hydroxylation, 84-91 Meobal,84 0-, S- and N-alkylhydroxylation, 80-84 Metabolic energy, see Respiration aromatic hydroxylation, 91-94 .Metaphoxide, 47 desulfuration, 94-96,620 , 473 epoxidation,84-91 , 99 ester oxidation, 94-96 Methiochlor, 99 nitrogen and thioether oxidation, 96-99 Methomyl,453 substrate specificity, 75-78,121-122 Methoprene, 489 substrate binding spectra, 116-121 , 472, 535, 576 Microsome, 63 N-Methylcarbamate, 18,283,482,533, see enzyme activity, 61-114 also Carbamate modern concept by Claude, 63 3-Methylcho1anthrene, 135,615 morphology, 63-66 Methylenedioxyphenyl compound, 127-135, Milkweed bug, see Oncopeltus fasciatus 422-424,631-635 Milliped derivatives, 127-132 and hydrogen cyanide, 432 effects on mammals, 631-635 insensitivity, 485 interaction with cytochrome P450, 125-130 Mipafox,470 mechanism of action, 131-135 Mirex, 135, 137,446,579,683 spectral changes in microsomes, 128-130 Mitochondrion structure and activity, 422-424 aging of, 371 synergism, 62,130-131,631-635 albumin requirement, 371 see also 1,3-Benzodioxole, Synergist electron transport system, see Respiratory Methylparaoxon, 464 chain Methyl parathion, 11, 12, 382,438,446, of fHght muscle, 356 479,493,579,581,582,623,634, membrane permeability, 358 650,677,679 metabolism, functional, 354-360 de methylation of, 194 requirement for bovine serum albumin, 371 2-Methylpropyl-2-propynyl phenylphospho- respiration, 354-360 nate, 130 Mitochrome, 371 Mevinphos, 470, 581 Modulator, 298 MGK-264, synergist, 130 Monoamine oxidase in endoplasmic reticulum, 66 Microsomal mixed-function oxidases, 61-114 Monochloro schradan, 288 and insecticide metabolism, 61-114, 124- Monocrotophos,470 127,465,533-541,610 Musca domestica, 9-11,47,50,116,124, and resistance, 140-142,533-541 137,161,167,184,185,356,357, catalytic events, 72-75, 122 359,362,386,409,410,475,488, electron transfer, 72, 122 489,510,515,516,524,527-535, oxygen binding and activation, 74-75, 122 538-540 Index 763

Musca domestica (cont'd) Nerve membrane (cont'd) insecticide-resistant strains, 138-141 potential, 233, 237, 241, 246 Muscarine, 231 action, 239-243 Muscarinic receptor, 261 effects of insecticides, 330-348 Muscarone,316 graded responses, 237-239 Mustard beetle, see Phaedon cochleariae resting, 233-237 Mutagenicity, tests for transient changes in, 237 cytogenic mitotic analysis, 565, 566 presynaptic, 298 dominant lethal, 562, 565 events occurring at, 250-252 host mediated assay, 562, 564 see also Nervous system Mutant aliesterase theory, 529 Nerve poison, see Neurotoxin Mutation Nervous system, 229-270, 297-326, 327-352 defined, 556 axonic conduction, 229-248, 328 somatic, 557 comparative pharmacology, 257-265 Myelination, 263 comparative physiology, 229-270 Mylone, 697 effects of insecticides, 330-349 Myzus persicae, 360,378,432,526,531 electrophysiology, 232-248 integrity, 229-232 junctional transmission, 248-257, 264-265 NADH, 74, 75, 97,128,134,155 and drug action, 259-262 NADH oxidase, 377 Neurological dissimilarities and drug action, inhibitor, 387 262-265 NADPH-cytochrome c reductase, 66, 69,70, similarities and drug action, 257-262 97, see also Microsomal mixed-func• Neuromuscular junction, 248-257,297-326, tion oxidases 329-330 Naphthalene, 92,94,138,536 and drug action, 259-262 hydroxylation, 96 comparative pharmacology, 260, 264-265 Naphthalene-l,2-oxide, 92, 93 effects of insecticides, 330-349 a-Naphthyl acetate,S 29 events occurring at, 250-257, 329-330 Narcotics transfer, transplacental, 25 structure, 249-250, 298 National Clearing House for Poison Control transmitter turnover, 256 Centers, 650, 654 see also Acetylcholine receptor, Nervous National Institute of Health(NIH), 91-96 system Neoplasia, 557 Neuron, 230,297,298 Neoseiulus fallacis, 533 Neurospora, 584,590 Neostigmine, 317,319 Neurotoxin, 26, 229-232, 304, 309 Nephotettix cincticeps, 515,531 delayed action, 264 Nereistoxin, 231, 315-317,343-345 Neurotransmitter, 259, 297, 299, see also Nernst equation, 236 Neuromuscular junction Nerve action potential, 239-243, see also Nicotiana gossei, 432 Nerve membrane N. sp. alkaloids, 418-419 Nerve degeneration, 264 N. tabacum, 432 Nervous integrity, 229-232 Nicotine, 28, 84, 231, 373,419,420,451, disruption, 230 468,664 Nerve membrane, 232-248, 328-330 metabolism, 85, 96 conductance, 245-248 nerve action, 315, 340-343 measurement by voltage clamp, 245-248 poisoning in humans, 664, 665 depolarization, 246, 329 protonated,419 impedance, 243-245 structure vs. activity, 418-422 ion currents in, 239-243 Nicotine adenine dinucleotide, reduced, see ion permeability, 233-237, 328 NADH penetration, 26-33,457-459 Nicotinic postsynaptic, 298, 329 receptors, 261 events occurring at, 253-254, 329 synapse in insect, 315 764 Index

Nicotinoid,418422 Organophosphorus insecticide (cont'd) mode of action, 315, 340-343, 418419 microsomal oxidation, 79-99 structure vs. activity, 418422 penetration, 3-58 Nirosan, 441, 495 poisoning, treatment of, 292-293, 656-660 Nissol, 474, 475 resistance to, 524-533,537-538 Nitrobenzene reductase, 166 selective toxicity, 468472 Nitrogen mustard, 560 structure-activity relationships, 402409 Nitrogen oxidation, 96-99, see also Micro• reactivity, 403404 somal mixed-function oxidases stereospecificity, 407409 4-Nitrophenol, phosphorylation of, 184, see steric effects, 404-407 also Conjugation teratogenic, mutagenic, and carcinogenic p-Nitrophenyl methylcarbamate, 284 effects, 579-587 Nitroreductase, 164-166 toxicity, 468-472 No pest resin strip, see Dichlorvos see also names of individual insecticides Nornicotine, 84, 419, 420 Organothiocyanates Nutrition and insecticide interaction, 635-637 metabolism, 207-208 synergists, 127,632 n-Octylamine, 118 Organotin, 542 Ohm's law, 245 Ovex, 622 Oil-water partition 1r constant, 400, see also Oxidase, microsomal, see Microsomal mixed• Physicochemical parameters function oxidases Oligomycin, 384, 385 Oxidation of insecticide Olive oil, 11 microbiological, 688-689, 698 OMPA, see Phosphoramidate insecticide microsomal,61-114 Oncogen, 557 photo-, 692 Oncopeltus !asciatus, 161 see also Microsomal mixed-function Opportunity factor, 469, 470 oxidases Organochlorine insecticide, 36, 135, 612- Oxidative phosphorylation, see Phosphoryla- 619, see also Hydrocarbon, chlorinated tion, oxidative biomagnification, 612 Oxime therapy, 290-293,659 inductive effect, 616-619 Oxime-2-PAM,291 tissue storage, 4042, 459462, 612-:616 Oxycytochrome P450, 74 Organophosphate, see Organophosphorus in• secticide Pantala j1avescens, 359 Organophosphorus insecticide, 47,82,149, PAP, see 3' -Phosphoadenosine-5' -phosphate 153,164,187-197,231,274,277, Paraoxon, 11, 13,95,96, 151-155, 194,274, 278,280,402409,480,512,536- 275,278,286,404,525,526,537, 537,579-587,619-630 585,622,625-627,630,631,693 effect on acetylcholine receptor, 317-319 Paraoxonase, 152,620 glutathione dependent metabolism, 187-196 Paraquat, 693 dealkylation, 188-195 Parathion, 20,47,50,62,78,79,95, 101- dearylation, 195-196 103,136,152,164,165,288,317, hydrolysis 380,383,404,438,461,468,479, by amidase, 162-164 525,526,531,538,579-582,621- by carboxylesterase, 156-160 624,631,634,636,637,650,656, by hydrolases, 149-156 657,677-679,687,693,699-701 in environment, 697-698 Partition coefficient, 9, see also Physico- inhibition of acetylcholinesterase, 276-281 chemical parameters factors affecting, 286-289, 402409 'Y-PCCH, 202 recovery, 290-291 PO organ, 237 interactions involving, 619-631 Penetration, 3-58,448-462,542 antagonistic, 621-627 and ionization, 6,16-17,457-458 synergistic, 628-630 assay, 450-457 Index 765

Penetration (cont'd) Phosphorylation, oxidative, 366-372 effect of method of administration, 50-51 mitochondrial, 366-372 Fick's law of diffusion, 13 rate, 286-289 central nervous system, 26-33 uncoup1ed,484 kinetics of, 12-16 see also Respiration monophasic, 13 Phosphotransferase, 184, see also Conjugation multiphasic, 14,44-46 Phosphotriester hydrolase, 154, see also quasisynergists, 51 Esterase, Hydrolase rate of, 15,28,46-50,451,509 Phosphotriester hydrolysis, 149-156, see also reduced in resistance, 542-543 Esterase, Hydrolase through gut, 16-20 Photodieidrin, 88 through integument, 6-12, 448-449 Photoreaction of insecticide, 691-692 through internal membranes, 16-33,457- photodecomposition, 691 459 photooxidation, 692 'Y-2,3,4,5,6-Pentachlorocyclohex-7-ene, 198, photoreduction, 692 202 Phoxim, 471 Pentachloroketone, 22 Phthalthrin, 207 Pentachlorophenol,382 Physicochemical parameters poisoning treatment, 665-666 and insecticide action, 398-427 Peptidase,184 Hammett a constants, 398-399 Periplaneta americana, 7,9, 12, 13.31-33, Hammett equation, 398 354,358,362,368-370,375,379, oil-water partition ('/I') constant, 400-402 382, 388 importance in microsomal metabolism, 77 Permeability, 238, 328, see also Nerve mem- importance in penetration, 8, 459 brane polar and steric constants, 399-400 Pesticide, see Insecticide Picrotoxin, 260 Phaedon cochleariae, 14,44 Piericidin A, 378, 379, 388 Pharmacodynamics, see Absorption, Penetration B, 378, 379 Pharmacology, comparative, 257-265, see Pieris brassicae, 357 Nervous system P. rapae, 366 Phenobarbital, 135-138,623 Pinocytosis, 6 Phenylbutazone, 617,618 , 51, 80-82, 99, 121, 127- Phormia rehina, 357,359,360,366,370 131, 136, 137,208,533,539,632- P. te"aenovae, 9 635, see also 1, 3-Benzodioxole, Phosdrin, 623, 657 Methylenedioxyphenyl compound, Phosphamidon, 83, 622, 623 Synergism Phosphatase, 525, 526, 529, 620, see also Pit viper venom, 229 Esterase, Hydrolase Placental membrane, 25 Phosphate, conjugation, 184-185, see also transfer by diffusion, 25 Conjugation Pneumonitis, 652 Phosphatidylcholine, 70 Poisindex, 655 3' -Phosphoadenosine-5' -phospha te(P AP), 182 Potential 3'-Phosphoadenosine-5'-phosphosulfate(PAPS), excitatory, 253, 254, 329 182 inhibitory, 329 Phosphodiester hydrolase, 155-156, see also postsynaptic, 253, 254, 329 Esterase, Hydrolase presynaptic, 250 Phospholine,318 resting, 233-237,246 Phospholipid, 70 see also Nerve membrane, Neuromuscular Phosphoramidate(OMPA),82 junction Phosphoric acid, 532 Pralidoxime chloride, 292, 293,612,659, triester-glutathione-S-aikyltransferase, 195 see also Oxime therapy Phosphorothioate, see Organophosphorus in- Prodenia eridania, 138, 139, 167, 182 secticide Progesterone, 374 766 Index

Proinsecticid<; 469 Respiration (cont'd) Proline dehydrogenase, 360 oxidation of Proline oxidation, 359 fatty acids, 359 in flight muscle of insect, 359,360 Q-glycerophosphate, 354-358 Propoxur, 80, 94, 101,538,539 proline, 359-360 Propylisome, 136, 137,632 pyruvate, 358-359 n-Propyl paraoxon, 96 oxidative phosphorylation, 366-372 Propynyl phosphonate ester synergist, 127, uncoupling agents, 381-385 632 respiratory chain, 361-366 Protein insecticides as inhibitors, 373-381 binding, of insecticide, 21, 459-462,609- Respiratory chain, 361-366, see also Respira• 610 tion tanned, 8 Resting potential, 233-237, 246, see also Nerve ,470 membrane Pseudomonas putida, 68 Reticulum, endoplasmic, 63, see also Micro- Putidaredoxin,70 some Propynyl oxime ether synergist, 632 Rhizobium spp., 165 Pyrethrin, 12,43-46,62,89,102,207,373, Rhodanese, 186,466, see also Cyanide 461,485,486,536,540,632,663- Ring cleavage of insecticide, microbial, 689 664, 692, see also Pyrethroids Rocky Mountain Poison Center, 655 pyrethroids, 13,44,90,91,207,336-339 Ronnel, 539, 623 conjugates in metabolism, 207 Rotenoids, 207, see also Rotenone effect on nervous system, 336-339 Rotenone, 80, 90, 91, 102,170,207,372, hydrolysis, 160-161 374-378,386-388,441,591-592, microsomal metabolism, 89-91 664,692 poisoning, treatment of, 663-664 carcinogenicity,S 91-5 92 resistance to, 540 conjugates, 207 toxicity, oral, 433-438 effect on respiration, 374-378 Pyrethrum, 127, 136, 160, 432, see also microsomal metabolism, 90-91 pyrethroids poisoning, treatment for, 664 pyridine-2-aldoxime methiodide, 291 site of action, 374-378 Pyridostigmine,319 Ryania,663 Pyrrhocoris apterus, 487,488 Pyruvate oxidation, 358 Sabadilla, 663 Saccharomyces cerevisiae, 364,582 Quassia, 663 Safrole, 136, 137, 208 Quelea quelea, 441 Salicylanilide, 383 N-Salicyloyl anthranilate, 383 Salmonella thyphimurium, 569,582 Rabon, SIS histidine auxotroph, 563 Ray, electric, 304 Saltatory conduction, 263, see also Nerve Receptor, see Acetylcholine receptor membrane Reduction, microbiological Samia cecropia, 273 of insecticide, 689 S. cynthia, 363 Reflex loop, 230 Sarcophaga barbata, 357, 366 Renshaw cell, 231 S. bullata, 366 Resistance, see Insecticides, resistance to Sarin, 317,637 Respiration Saxitonin, 229, 258 as a basis for selectivity, 387, 484-485 Schistocerca gregaria, 357 biochemistry of, 354-372 Schistosomiasis drug, 383 effect of insecticides on, 372-387 Schradan,97,101,438,441,461 Q-glycerophosphate shuttle, 356 SD-1l319, 50,52 inhibitors, 389-390 Sea lamprey, 463 Index 767

Selectivity Superoxide anion, 75 at species level, 438-439 Superoxide dismutase, 133 based on binding, 459-462 Surface rinse method, 450 based on differences in target site, 476-486 Synapse, 297, 329 based on differential detoxification, 462- cholinergic, 249, 297,298 473 m uscarini c, 261 based on excretion, 462 nicotinic, 315 based on penetration differences, 448-459 see also Nervous system, Neuromuscular ecological, 445-446 junction physiological, 447-448 Synergism, mechanism of, 51, 131-135, 632 polyfactorial nature, 491-495 Synergist ratios, vertebrate, 433-438 binding spectra, 121, 128-129 toxicity correlations, 441-444 biphasic interactions, 634-635 unexploited targets, 490-491 interaction with cytochrome P450, 128-130 Selectophore, 468, 471 interaction with microsomal oxidases, 127- Self-synergism, 470 135 Serratia marcescens, 569 structure-activity relationships, 422-424 Sesame oil, 127,632 toxic interactions in mammals, 632-634 Sesamex, 50-53,101,127,533,535,633 types, 127,632 Sheep blowfly, see Lucilia use in resistance,S 20-5 21 Silkworm, see Bombyx mori Synthesis, "lethal," 385 Simazine,698 Systox, 587,623 SKF 525-A, 610, 632, 633 Snake venom, 155 Tabun, 152 Sodium conductance, 339, 343, see also Taft's polar substituent constant, 399-400, Nerve membrane 406-407, see also Physicochemical Sodium fluoroacetate, 441, 473, 475, see parameters also Fluoroacetate Taft's steric substituent constant Es, 399- Soil cultivation with insecticide, 696 400, 406-407, see also Physico• Solubility of insecticide, aqueous, 695-696, chemical parameters see also Physicochemical parameters TCA cycle, 357, 358, see also Respiration Southern armyworm, see Prodenia eridania TDE,524 Spectroscopy, optical difference-, 11 7 Temik,660 Spider mite, see Tetranychus urticae Tenebrio molitor, 167,379,386,487,488, Steroid 489 glucosyltransferase, 181 Tepa, 589-591 hormones, 76, 212 TEPP, see Tetraethylpyrophosphate sulfate, 178 Teratogenicity in urine of pregnant mares, 178 defined, 556 Stirofos, 441, 456, 461, 482 tests, 561-562 Streptomyces griseus, 380 in chick embryo, 561 S. mobaraensis, 378 in mammal, 562 Strychnine, 231 Testosterone hydroxylation, 619 Styrene oxide, 167, 168, see also Epoxide Tetanus, toxin, 231 hydrase Tetracyanoethylene, 284 Substrate inhibition, alternative, 534 Tetracycline, 608 Succinate oxidation, 373, see also Respira• Tetraethylpyrophosphate(TEPP), 95,152, tion 153,291,317,404,622,657 Sulfate conjugation, 182-183, see also Con• Tetram,319 jugation Tetramethylammonium, 286 Sulfoxidation, 99, see also Microsomal mixed• Tetranychus teiarius, 378 function oxidases T. urtica, 512,527,530 Sumithion, 164, 382,650 Tetrodotoxin, 229, 230,245, 258,432,485 768 Index

TH-6040, 489, 490 Triethyltin, 385 Thalidomide, 26 2,3,5 -Trimethylcarbamate, 51 Thanite,51 Trimethylphosphate,584 Thiocyanate, 186 N,N',N" -Trimethylphosphorarnide, 83 formation from cyanide detoxication, 186 Trimethyltin, 385 see also Organothiocyanates Tri-o-cresylphosphate(TOCP), 138,469,626, Thioether oxidation, 96-99, see also Micro- 629,630 somal mixed-function oxidases Triphenylphosphate, 138 Thiotepa, 589-591 Trithion,623 Tirpate, 660 Tropital synergist, 632, 633 TMB-4, 291, see also Oxime therapy Trypan blue, 30 Tobacco budworm, see Heliothis Tse tse fly, 446 Tobacco hornworm, see Manduca Tuberolachnus salignus, 458 Tobacco wireworm, see Conoderus d-Tubocurarine, 260, 301 Tolbutamide, 622 Tumorigen, 557 Torpedo californica, 304, 305 T. electroplax, 304-308 UC-10854, 84 T. marmorata, 303-305,313,318,319 UDP glucosyltransferase, 181, see also Con• T. ocellata, 304, 305 jugation , 574, 618, 674,675 UDP glucuronyltransferase, 179, see also Toxicology, environmental, 669-713 Conjugation biomagnification,684-686 Uridl.'e diphosphoglucuronic acid, 179, see consequences, 100-103 also Conjugation insecticide disappearance, 687-699 residues, 670-684 Vapam, 697 occupational hazards, 699-706 Vapona strip, 584, see also Dichlorvos Toxifile, 655 Veratridine,259 Toxline of the National Library of Medicine, Veratrine, 259, 431 655 Veratrum sp., 431 Trans-6,7-dihydroxydihydroaldrin, 85, see Vertebrate selectivity ratio, 433-438 also Aldrin trans-diol for insecticides, 434-435 Transducer action, 238 for mammalicides, 434 Transmission, junctional, 248-257,259-262, see also Selectivity 264-265, see also Neuromuscular junc• Vitamin K, 388 tion Volatilization of insecticide, 693-694 Transmitter substance, 329, see also Neuro• Voltage clamp technique, 245-248 muscular junction experiments, 337, 339 release, 250, 257 graphic presentation, 246-248 quantal nature, 250 membrane potential change, 246 termination of action, 256 see also Nerve membrane turnover, 256-257 VSR, see Vertebrate selectivity ratio Tribolium castaneum, 527,538, 540 Tributyltin chloride, 542 Warfarin, 617 Tributylphosphorotrithioate, 138 Water--oil partition 7T constant, 400, see also Tricarboxylic acid cycle, see TCA cycle, Physicochemical parameters Respiration Wax, epicuticular, 7, 8,10,12 Trichlorfon, 196,582-585 Wax moth, see Galleria 2-(2,4,5-Trichlorophenyl)propynyl ether Weaver bird, see Quelea synergist, 130 3,3,3-Trichloropropene oxide, 96, see also Yeast, see Saccharomyces cerevisiae Epoxide hydrase Yellow mealworm, see Tenebrio molitor Trichoplusia ni, 161,509,541 3,4,5-Triethylphenyl-N-methylcarbamate, 5 I Zectran, 84, 101