Subject Index

Abate, properties and uses 338 Alfalfa 120, 157, 175,209,232,276,375, - synthesis 338 422 Acaricides, definition 3 Algae control (see also Slime control) Acetaldehyde 111, 378 5, 115 Acethion, properties and uses 359 Algalol, see Aretan - synthesis 359 Algicides, definition 3 Acetone oxime N-phenylcarbamate, see Alipur 229 Proxypham Allethrin 131 If. 3-( et-Aceton y lbenzy I) -4-h ydroxycoumarin, Allyl alcohol 89 see Warfarin Allyl bromide 35 3-( et-Acetonyl-4' -chlorobenzy 1)-4-hydroxy- Allyl chloride 39 coumarin, see Coumachlor Allyl isothiocyanate 260 Acetophos, properties and uses 351 Alodan, permissible concentration in air - synthesis 351 65 3-Acetyl-6-methylpyrandione-2,4, see - properties and uses 52, 64 If. Dehydroacetic acid - synthesis 64, 268 1-Acetyl-1,2,3,4-tetrahydroquinoline, , properties and uses see Kyuzol-A 445, 446 Acrex, see Dinobuton Ametryne 436 Acrolein 111 Amiben 148 Acrolein phenylhydrazone 279 Amides, pesticidal properties 124 If. Acrylonitrile 122, 128 Amidithion, properties and uses 363 Acylate, properties and uses 203 - synthesis 363 - synthesis 203 Amines, pesticidal properties 83 If. Adamsite 390 Amibenzenesulfonyl , see Aerogels, see Silica gel Compound ME-9057 Aerosol compositions 24 , see Matacil Aerosols 12, 20, 22 If. Aminoguanidine, synthesis 429 Agriculture, losses from pests 1, 5 If. 2-Amino-4-methyl-5-carboxanilidothiazole, Agronal295 see Seedvax Agvitor, properties and uses 384 Aminoparathion 324 - synthesis 384 5-Amino-3-phenyl-1,2,4-triazolyl-1- Alanap, properties and uses 152 bis( dimethylamido )phosphate, - synthesis 152 see Wepsin Alcohols, pesticidal properties 89 4-Amino-1 H -pyrazolo-3,4-pyrimidine Aldehydes, pesticidal properties 111 If. sulfate 439 , properties and uses 197, 198 3-Amino-1,2,4-triazole, see Amitrole - synthesis 198 Amiton, see Tetram , analytical method 61, 62 Amitrole, mode of action 429 conversion to 61 - properties and uses 427-430 permissible concentration in air 62 - synthesis 429 properties and uses 42, 53, 60 If. Ammate, properties and uses 262, 263 synthesis 60, 61 - syntheses 262 tolerance 62 Ammonium sulfamate, see Ammate

449 450 Subject Index

Ammonium thiocyanate, properties and Aryloxyacetylhydroxamic acids, pesticidal uses 252, 259, 429 properties 160 Amoben, properties and uses 217 Aryloxyalkylcarboxylic acids, pesticidal - synthesis 217 properties 157 ff., 160, 175 ff. Amophos 375 Aryloxybutyric acids, pesticidal properties AMS, see Ammate 173 ff. Amylarsine oxide 390 Aryloxypropionic acids, pesticidal 396, 405, 406 properties 172 ff. Aniline 83 Arylsulfonic acid esters, ovicidal properties Animal parasite control 50, 65, 76, 255, 271,272 257,296, 299, 303 ff., 317, 332-334, AsCu compound 389 342, 383, 387, 397, 424 Asparagus 232, 422 Animals, number of species 1 Asulam 204 Anisic acid esters, pesticidal properties 141 Asunthol, see Anthracene oil 21, 31, 32 Atratone, properties and uses 438 Anthranilic acid esters, pesticidal properties - synthesis 438 141 Atrazine, properties and uses 435, 436, 438 Anticoagulants 115 - synthesis 436 Antifeeding agents 299 Attractants 3, 10, 89, 139 Antio, see - definition 3 Antiseptics, definition 3 Auxins 138 Antu, properties and uses 227, 237, 238 Avadex, see Di-allate - synthesis 238 Avenin, properties and uses 317 APC 192 - synthesis 317 Aphicides, definition 3 2-Azido-4-ethylamino-4-tert-butylamino-s- Aphidan 366 triazine, see WL 9385 Aphid reproductive rate 2 2-Azido-4-isopropylamino-6-methyl- mercapto-s-triazine, see C-7019 Apholate 318 Azinphos ethyl 372 Aphoxide 318 Azinphos methyl, oxygen analog 372 Apples 100, 102, 155, 188, 238, 264, 274, - methyl, properties and uses 371, 372 283,289, 315, 392, 396, 405, 418, 427, - methyl, synthesis 372 432 Azobenzene, properties and uses 280, 281 pest-caused losses 1, 5 - synthesis 281 Apricots 366 Azobenzide, see Azobenzene Aramite and cancer 266 Azo compounds, pesticidal properties photodecomposition 266 278 ff. properties and uses 266, 267 Azomat 393 stabilization 266 Azosulfides 279 synthesis 266 Azoxybenzene 278 Arboricides, definition 3, 5 Aresin, see Monolinuron Aretan, properties and uses 292 B/77, see Fitios B-169-ferrocyanide, see Fungilon - synthesis 292 B-995, see DMSA Argox 295 Bacteria control 30, 82, 84 ff., 91, 93, 102, Arsenic acid, synthesis 389 105, 107, 111, 118, 142, 148 ff., 213, and cancer 387 227,275,276,280,283 ff., 387, 397, compounds, irritant properties 390 400, 409, 443, 445 compounds, pesticidal properties 387 ff. Bactericides, definition 3 in tobacco 387 Baits (see also Rodent control) 12, 25 N-Aryl-N',N'-dialkylureas, syntheses 230 Balding 446 Aryloxyacetic acid derivatives, pesticidal Banol, see Carbanolate properties 159 ff. Banvel-D, see Dicamba - acids, reactions and syntheses 161 ff. Banvel-T 147 Aryloxyacetylamino acids, pesticidal Barban, analytical method 202 properties 159 - decomposition 202 Subject Index 451

Barban, persistence 202 BHC, oxidation 68 - properties and uses 184, 185, 202 permissible concentration in air 44 - syntheses 202, 203 properties and uses 32, 42 If., 50, 68, Barium carbonate 446 69, 104, 166, 216, 287, 295 Barium chloride 446 smokes, composition 23 Barium fluosilicate 444 stereoisomers 42 If; Barium polysulfide, see Solbar synthesis 46 If. Barley 125, 155, 202, 210, 211, 438 Bi-58, see Barthrin 131 If. Bicyclohcptylcarbinol norcamphane- Bayer-22,555, see Dexon methanol 91 Bayer-30,686, see Eradex Bidisin 155 Bayer-32,394, see Fungilon Bidrin, properties and uses 314 Bayer-37,344, see Mesurol - synthesis 314 Bayer-39,007, see Baygon Binapacryl 100 Baygon, properties and uses 193, 194 Bi-PC, properties and uses 201, 229 - synthesis 193, 194 - synthesis 201 Baytex, see Biphenyl, properties and uses 26, 27, 67, Beans 1, 104, 113, 115, 159, 174,206,209, 82, 294 210,216,419 - tolerance 27 - pest-caused losses 5 Bird repellents 117 Bees and organophosphorus compounds Birlane, properties and uses 314, 315 304 If. - synthesis 314, 315 Beets 113, 155,204,209,211,292 Bis( 4-chlorophenoxy)methane, see Mikazin Benachlor 68 Bis(3,4-dichlorofuranon-5-yl-2) ether Benefin 84 396, 397 Benlate, properties and uses 418 Bis(2,4-dichlorophenoxyethyl) phosphite 308 Benzene hexabromides 44 1,1' -Bis(3,5-dimethylmorpholinecarbamoyl­ Benzene hexachloride, see BHC methyl)-4,4' -dipyridylium chloride, Benzenesulfonyl fluoride 276 see PP-745 Benzimine, synthesis and uses 152 Bis(ethylxanthogen) disulfide, properties Benzoic acids, pesticidal properties 142, and uses 177, 178, 180, 181 144 If. - disulfide, synthesis 181 Benzopyrenes 31, 32 Bis( ethylxanthogen) tetra sulfide 181 Benzoquinone 4-chlorobenzoylhydrazone Bis( ethylxanthogen) trisulfide, properties 279 and uses 177, 178, 181 Benzoquinone monoguanidinehydrazone - trisulfide, synthesis 181 thiosemicarbazone, synthesis and uses Bis(methylxanthogen) disulfide, properties 280 and uses 180 Benzoquinones 115 - disulfide, synthesis 180 4-Benzothienyl N-methylcarbamate, Bis(pentachlorocyclopentadien-2,4-yl) 55 see Mobam Bis(pentachlorophenyl) disulfide 49 Benzotriazole, formative elfect 427 Bis(tetrachloroethyl) disulfide 249 Benzoxazolinone, synthesis 414 Bis(trichlorophenyl) disulfide 49 Benzoylhydrazinoaniline 280 Biuret, properties and uses 225 Benzoylhydrazone of quinone oxime, Bladafume, see Sulfotepp see Cerenox Bladan, see TEPP Benzylamine 83 Blastin, properties and uses 92 Benzyl benzoate 141 - synthesis 92 Benzylphenol 94 Blastogenic elfect 6 Betanal, properties and uses 204 Blood anticoagulants 400 If. - synthesis 204 Boa ts, marine growths 297 Beta-oxidation 160 Boliden-bis 389 BHC, analytical method 46 Bordeaux mixture, synthesis and uses dehydrochlorination 45, 49 188, 442 formulations 14, 18, 21 , pesticidal properties 447 isomerization and isomers 43-46 Bornyl thiocyanoacetate, see Thanite 452 Subject Index

Bran 111 C-2059, see Fluometuron Brassisan, properties and uses 48, 49, 81 C-3126, see Patoran - synthesis 81 C-3470, properties and uses 232 Bread 118 - synthesis 232 Brestan, properties and uses 297, 299, 301, C-6989110 302 C-7019 438, 439 - stability 302 C-8353 192 Broccoli 195 Cabbages 81, 109, 180,209, 314, 315, 375, Bromacil, properties and uses 421 437 - synthesis 421 - pest-caused losses 1, 5 5-Bromo-3-sec-butyl-6-methyluracil, Cacao trees 316, 392 see Bromacil Cacodylic acid, properties and uses 5-Bromo-3-tert-butyl-6-methyluracil, 391, 393, 394 see Compound 733 - acid, synthesis 393 N -4-Bromo-3-chlorophenyl-N'-methyl- Cacodyl oxide, synthesis 393 N' -methoxymethylurea 235 Cadmium-calcium-copper-zinc chromate- I-Bromo-3-chloropropene 40 sulfate 443 Bromodiphenyl sulfones as acaricides 243 , properties and uses 388, Bromonitrostyrene, properties 80 389 Bromophenylethane 67 - arsenate, syntheses 389 N -4-Bromophenyl-N' -methyl-N'-methoxy- Calcium arsenite, properties and uses 388 urea, see Patoran - arsenite, synthesis 388 Bromophenyl sulfones 243 Calcium chloride chlorate 445 Bromophos, persistence 335 Calcium hypochlorite 445 - properties and uses 320, 321, 335, 337 Calcium polysulfide 188,441 - synthesis 335 Calcium propionate 118 Calcium sulfamate 263 Bromophos-ethyl 335 Calcium tetrathionate, properties and uses Bromostyrene 67 246, 264, 442 Bromoxynil, properties and uses 150 - tetrathionate, synthesis 264, 442 - synthesis 150 Camphene, chlorination 50 ff. Bromoxynil octanoate, properties and uses Cancer (see also Blastogenic effect) 150 6,32, 266, 387, 425 - octanoate, synthesis 150 Captan and fermentation of grapes 247 Bulan 80 - properties and uses 240, 247-250, 263 Bulbosan 81 - synthesis 248 Butifos, properties and uses 259, 308, 376 Captan analog No.6, see Mesulfan - synthesis 376 , cholinesterase inhibition (see Butiphos, see Butifos also specific compounds) 183 Butonate, properties and uses 383 - structure-activity relationships 183 ff. - synthesis 384 Carbamic acid derivatives, pesticidal N-Butoxyphenyl-N',N'-dimethylurea 226 properties 183 ff. p-Butoxy-,B'-thiocyanodiethyl ether, - acid esters, syntheses 186 ff., 198 ff. see Lethane-384 Carbanolate 190 Butyl bromide 35 Carbathene, see Thioneb Butylcarbitol piperonate 413 , metabolites 189 N-Butyl-N',N'-dimethylurea 225 permissible concentration in air 188 Butyl mercaptan 308 properties and uses 184, 188 ff. 2-( 4-tert-Butylphenoxy)propyl-2- synthesis 188 ff. chloroethyl sulfite, see Aramite tolerance 189 3-sec-Butylphenyl N -methylcarbamate, Carbolic oil 31 see H-28 Carbon disulfide, explosive concentrations 3-tert-Butylphenyl N-methylcarbamate, 181 see H-22 disulfide, properties and uses 36, 37, Butylphenyl N-methylcarbamates 184 178-182,211-222,246, 247, 260, Butynediol 89 431,432 Subject Index 453

Carbon disulfide, synthesis 182 Chemonite 389 Carbonic acid derivatives, pesticidal Chemosterilants 3, 122, 318, 396, 415, 439 properties 177 if. Chemotherapeutic index 283 - acid esters, syntheses 178 Cherries, pest-caused losses 5 Carbon sulfoxide 178 Chinomethionate, properties and uses 182 , permissible concen­ - synthesis 182 tration in air 37 Chipcote, properties and uses 291, 292 tetrachloride, properties and uses - synthesis 291 35, 36, 38, 181 Chloral, properties and uses 382, 383 tetrachloride, synthesis 36, 37, 55 - synthesis 71, 72 Carbonyl sulfide, synthesis 208, 209 Chloralchloroacetamide 125, 128 , properties and uses Chloramines Band T 275 364, 366 Chloranil, properties and uses 48, 49, 105, - synthesis 366 115 - tolerances 366 - synthesis 115 Carbophos, see Chlorazine, properties and uses 420, 421, Carbothion, analytical method 213 437 decomposition 212 - synthesis 420, 421 properties and uses 206, 211-213, 254 Chlorbenside, properties and uses 241, 242 stabilization 212 - synthesis 242 synthesis 213 Chlorbenside sulfoxide and sulfone 242 Carboxylic acid ami des and imides, , analytical methods 57 pesticidal properties 124 if. analogs 59 acid esters, pesticidal properties 122 if. properties and uses 42, 52, 55 if., 59 acids, pesticidal properties 118 if., stabilization 57 130 141 153 if., if., if. synthesis 56 Carrots 109, 125, 147, 148, 155, 184,200, tolerance 57 209,226, 232, 234, 235, 314, 384, 436, Chlordene 56-59 437 Chlorendic acid 59, 289, 292 Castrix, properties and uses 422 Chlorex 107 - synthesis 422 Chlorfenidim, see Monuron Cattle 75, 255, 257, 333, 334, 382 Chlorfenson, see Ovex Cauliflower 125, 437 Chlorflurazole, properties and uses 418 CBP-5540 Chlorinat, see Barban CCC, properties and uses 88 Chlorinated terpenes, stabilization 57 - synthesis 88 dioxide 445 CDEC, decomposition 223 Chloroacetic acid, properties and uses - properties and uses 223, 224 120, 363 - synthesis 223 - acid, syntheses 120 Cereals (see also specific kinds) 1, 25, 423, Chloroacrylic acid 122 424 Chloroalkylphenols, pesticidal properties Ceredon-Special 295 93,94 Cerenox, properties and uses 116, 117, 279, 2-ChloroaII yIN,N -diethyIdi thiocarbama te, 281, 282 see CDEC - synthesis 116, 282 Chloroaniline, synthesis 201 Ceresan, properties and uses 282, 294, 295, Chlorobenzaldehydes, pesticidal properties 298 112 - synthesis 295 4-Chlorobenzenediazothiourea, Ceresan-M, properties and uses 289 see Promurite - synthesis 289, 290 p-Chlorobenzenesulfonic acid, dimethyl Ceresan-Universal Nassbeize, see Aretan amide 275 Ceres an-Universal Trockenbeize, see Chlorobenzilate, analytical method 142 Methoxyethylmercuric silicate - properties and uses 92, 141, 142 Cheese 118 - synthesis 141 Chemistry of pesticides (see also specific Chlorobenzoquinone benzoyl hydrazone 279 compounds) 1 if. 6-Chlorobenzoxazolone 371 454 Subject Index

4-Chlorobenzyl phenyl ether 241 Chloro-IPC, see Chloropropham 2-Chloro-4,6-bis( diethylamino )-s-triazine, 2-Chloro-4-isopropylamino-6-diethylamino­ see Chlorazine s-triazine, see I pazine 2-Chloro-4,6-bis(ethylamino)s-triazine, Chloromaleic acid an iii des 128 see Simazine 2-Chloromethyl N -methylcarbamate, 2-Chloro-4,6-bis(isopropylamino)-s-triazine, sec CPMC see Propazine Chloromethylphenols, synthesis 169 Chlorobromomethane 367 Chloromethylphenoxyacetic acid, 5-Chloro-3-tert-butyl-6-methyluracil, see MCPA see T erbacil Chloromethylphenoxybutyric acid, 2-Chloro-4-tert-butylphenol 317, 318 see MCPB 4-Chlorobutyn-2-yl N -(m-mlorophenyl) 4-Chloro-2-methylphenoxyethanol, carbamate, see Barban synthesis 180 Chlorocarbonic acids, pesticidal properties Chloromethylphenoxypropionic acid, 177 ff. see Mecoprop 2-Chloro-3-( 4-mlorophenyl)propionic acid, Chloromethylphenyl dimethylformamidine methyl ester, see Bidisin 129 Chloromoline mloride, see CCC Chloromethylphthalimide, synthesis 371 Chlorocresol 168 l-Chloro-2-methylpropene-2, 3-Chloro-6-cyanonorbornanone-2 oxime see Methallyl mloride O,N-methylcarbamate, see Compound 2-Chloro-6-methylquinone benzoyl- UC-20047A hydrazone 279 l-Chloro-2,3-dibromopropane, Chloronaphthalene 68 see Nemagon Chloronitrobenzene, synthesis 201 2-Chlorodiethyl sulfide 368, 369 Chloronitroethanes 78, 79 9-Chlorodihydrophenarsazine, 2-Chloro-4-nitrophenol 331, 332 see Adamsite Chloronitropropanes 78, 79 2-Chloro-4-dimethylamino-6-methyl- Chloronitrostyrene 80 pyrimidine, see Castrix N -( Chloronorbornyl-2)-N',N' -dimethylurea 4-Chloro-3,5-dimethylphenoxyethanol 108 226, 230 Chlorodimethylphenoxypropionic acid 173 Chloroparacide, see Chlorbenside Chlorodinitronaphthalene 81 Chlorophene 51 4-Chlorodiphenyl sulfone, see Sulphenone 4-Chlorophenol, properties and uses 274 Chlorodiphenylsulfones, pesticidal - dissociation constant 309 properties 243 - synthesis 272, 273 Chloroethanol, see Chlorophenols, pesticidal properties 2-Chloro-4-ethylamino-6-diethylamino-s­ 94, 318 triazine, see Trietazine 4-Chlorophenoxyacetic acid 157, 161, 162, 2-Chloro-4-ethylamino-6-isopropylamino­ 172 s-triazine, see Atrazine 4-Chlorophenoxyaniline 232 2-( 4-Chloro-6-ethylamino-l ,3,5-triazine-2- Chlorophenoxyarsine, synthesis 394 ylamino)-2-methylpropionitrile, 2,4-Chlorophenoxyethanol 307, 308 see WL 19805 N -4-( 4'-Chlorophenoxy)phenyl-N',N'­ 2-Chloroethyl m-mlorophenylcarbamate dimethylurea, see Tenoram 185 4-Chlorophenoxyphenyl isocyanate 232 ",-(2-Chloroethylmercapto)propiomethyl- 4-Chlorophenyl benzenesulfonate, amide, synthesis 350 see Fenson 2-Chloroethyl phenylcarbamate 185 4-Chlorophenyl benzyl ether 241 2-Chloroethylphosphonic acid, see Ethrel N-(4-Chlorophenyl)carbamate 184 Chloroform, properties and uses 35, 121 4-Chlorophenyl-4'-mlorobenzenesulfonate, - synthesis 36 see Ovex Chloroguaiacolacetic acids 159 4-Chlorophenyl-4'-mlorobenzyl ether 241 4-Chloro-2 -h ydroxybenzothiazoliny1- 3- 4-Chlorophenyl-4'-mlorobenzyl sulfide, acetic acid 414, 415 see Chlorbenside Chlorohydroxydiphenyls 95, 96 p-Chlorophenyl mloromethyl sulfide, Chloroindan, see Chlordane synthesis 366 Subject Index 455 p-Chlorophenyl mloromethylsulfone, syn­ Citrus fruits 95, 366, 422 thesis 240 CMPT, properties and uses 127 N -4-Chlorophenyl-N' ,N'-dimethylurea, Coal-tar oils, composition 30, 31 see Monuron - oils, frost protection 33 4-Chlorophenylmethanesulfonamide, - oils, properties and uses 27,30 ff., 33 synthesis 250 Coke gas 441 N -4-Chlorophenyl-N'-methyl-N' -methoxy­ Complexons (see also Trilon B) 163, 175 urea, see Monolinuron Compound 47, properties and uses 253, 3-( 4' -Chlorophenyl)-5-methylrhodanine, 258 synthesis and uses 415, 416 - 47, synthesis 258 4-Chlorophenyl-2,4,5-trimlorophenylazo Compound 125 102 sulfide, see Mikazin Compound 732, see Terbacil N' -4-Chlorophenyl -O,N,N-trimethy 1- Compound 733 421, 422 isourea, see Trimeturon Compound 1068, see Chlordane Chlorophos, see Trimlorfon Compound AB 443 Chloropicrin and P compounds 78 Compound C-8874, see Iodophos-ethyl and SH compounds 78 Compound C-9491, see Iodophos permissible concentration in air 79 Compound C-I0015 196 properties and uses 38, 78, 79, 276 Compound M-l 155 synthesis 79 Compound M-74, see Chloropinene 50 Compound M-81, see Thiometon Chloropromurite, properties and uses 237 Compound MB-8882 275 - synthesis 237 Compound MB-9057 275 Chloropropham, properties and uses Compound MB-9555 275 185,186,200,202 Compound No. 23 222, 223 - synthesis 200, 201 Compound R-4461, properties and uses 375 4-Chloropyrocatemol from 2,4-D 165 - R-4461, synthesis 375 Chloroguinones, pesticital properties 115 Compound UC-20047 A, properties and Chlorosulfacide, see Chlorbenside uses 198 Chlorothene, permissible concentration in - UC-20047 A, synthesis 198 air 52 Concentrate spraying 10, 19, 24, 28 - properties and uses 52 Concentrated emulsions, see Emulsive - synthesis 52 concentrates p-Chloro-,8' -thiocyanodiethyl ether, see Contact herbicides, definition 4 Compound 47 Contact , definition 3 p-Chlorothiophenol 281, 366 Copper acetate, see 2-Chloro-l-(2,4,5-trimlorophenyl)vinyl Copper arsenate 389, 443 dimethyl phosphate, see Gardona Copper arsenite, see Paris green Chloroumbelliferone 341 Copper borate 443 6-Chloro-3,4-xylenyl N -methylcarbamate, Copper carbonate 443 see Carbanolate Copper compounds, pesticidal properties Chlorphos 336 442 ff. Chlorthion, properties and uses 331, 332, Copper ethylenebis(dithiocarbamate) 221 337 Copper naphthenate 130 - synthesis 331 Copper oxinate, properties and uses Chlorthion 331 410,411 Cholinesterase inhibition 183 ff., 303 ff., - oxinate, synthesis 411 309, 327, 368 Copper oxymloride 18,215,221,442,443 Chrysanthemumic acid, synthesis 135, 136 Copper pentamlorophenolate 105 Cidial, properties and uses 374 Copper phenylsalicylate, properties and - stability 374 uses 149 - synthesis 374 - phenylsalicylate, synthesis 149 Cinerins, air inactivation 132 Copper phosphate 443 - properties and uses 130 ff. Copper 8-quinolinolate, see Copper oxinate Ciodrin, see Crotoxyphos Copper sulfate, pesticidal properties 6 CIPC, see Chloropropham Copper sulfate-dihydrazine sulfate 278,443 456 Subject Index

Copper 2,4,5-trichlorophenolate 50, 103, 3-Cyclohexyl-5,6-trimethyleneuracil, 104,216 see Lenacil Co-Ral, see Coumaphos N -Cyclooctyl-N',N'-dimethylurea, Corn (see also Maize) 1, 112, 125, 147, 176, seeOMU 210,216,225,234,280,282,308,436, Cyclopropanecarboxylic acid anilides, 439 pesticidal properties 139 Coroxon 342 Cyoiane, see Dithiolane Cotoran, see Fluometuron Cypromid 127 Cotton and cottonseed 1-3, 49, 62, 65, Cystogon, properties and uses 222, 223 82, 84, 89, 104, 113, 115, 122, 155, 157, - synthesis 223 173,179,181,184,188,193,196,225, 229,231,233,234,236,254,259,280, 282, 290, 294, 308, 313, 318, 365, 369, D-263, properties and uses 113 370,372,375,376,418,419,423,438, D-497, properties and uses 113 44·5 2,4-D, dichlorophenol in 163, 166 goods, disinfectants 107 from 2,4-DB 175 from Falone 308 Coumachlor, properties and uses 402 impurities in 165, 166 - synthesis 402 photodecomposition 163 Coumaphos, properties and uses properties and uses 120, 157-159, 321,341-343 161-166, 171, 176,408 - synthesis 342 syntheses 165, 166 Coumaphos oxon, see Coroxon tolerance 165 Coumatetralyl, properties and uses 402 2,4-D esters, properties and uses 166-168 - synthesis 402 - esters, synthesis 167 CP 31675126 2,4-D salts, properties 163, 164 CP 50144 126 Dacthal, properties and uses 144, 152, 153 CP 52223 126 - synthesis 153 CPB, see Fenson Dalapon, properties and uses 121, 122 CPMC 190 - synthesis 121 Creolin, see Coal-tar oils DAS-893, see Dacthal Creosote oil 31 Dasanit, see Fensulfothion Cresol 93 Daxtron, properties and uses 404 Crotonic aldehyde 111 - synthesis 404 Crotoxyphos, properties and uses 312, DB-90S 82 313 2,4-DB oxidation to 2,4-D 175 - syntheses 313 - properties and uses 175 Crotylin 168 - synthesis 175 CRP-3281 DDD, seeTDE Cryolite, properties and uses 444 DDE 73 - tooth damage 444 DD Mixture 35, 38, 39 Cucumbers 264, 423 DDT 12, 20, 42, 50, 58, 63, 68, 76, 80, 91, Cuprocin 221 115, 240, 245, 256, 273, 275, 370, 371, Cuprous oxide, synthesis and uses 18, 443 388,441 Curare 428 analogs and homologs (see also specific Currants 65, 175 compounds) 74 If. Cyanamide 239 analytical methods 73, 74 Cyano-2,4-dichlorophenylacrylic acid, - C-14 labelled, synthesis 72 properties and uses 154 - composition 69 If. - acid, synthesis 154 DDT-dehydrochlorinase 73, 275 Cyanogen chloride 434 DDT dehydrochlorination 73, 76 Cyanox 336 - formulations 13, 14, 17-21 Cyanuric acid 434, 435 - hydrolysis 73 Cyanuric chloride, properties 435, 436 in the environment 74 - chloride, synthesis 434 in milk 74 Cyclethrin 131 if. isomers 69 If. Cyclohexanecarboxylic acids 139 permissible concentration in air 74 Subject Index 457

DDT persistence 74 4-Diallylamino-3,5-dimethylphenyl photodecomposition 73 N-methylcarbamate, see APC properties and uses 69 if., 74 Diallylchloroacetamide, see Randox residues, decomposition 73 Diammonium ethylenebis( dithiocarbamate), smokes, composition 23 see Amoben stabilization 73 , properties and uses 321, 338, 339 storage in fat 74 - synthesis 339 syntheses 71 if. Dibasic acids, pesticidal properties 152 if. telomerization 74 Dibenzo-l,4-thiazine, see Phenothiazine thermal decomposition 72, 73 Dibenzylamine 83 tolerances 74 Dibenzyl sulfide 352 DDT-type compounds, insecticidal Dibrom, see activities 74 if. Dibromobenzenes 67 DDVP, see Dibromobutene 40 Decachlor 55 Dibromobutyne 41 Decotex, see MCP A Dibromodichlorocyclohexane 44 Decyl alcohol as pesticide 89 1,2-Dibromoethane, properties and uses Decyl thiocyanate 253 35, 38, 39 Deet, properties and uses 142, 143, 151, - synthesis 38 - syntheses 151 3,5-Dibromo-4-hydroxybenzonitrile, Defoliant 2929 RP, properties and uses see Bromoxynil 259, 260 Dibromomethane 367 - 2929 RP, synthesis 259, 260 Dibromosalicylanilide 149 Defoliants 3, 5, 89, 143, 178, 236, 252, 254, Dibromotetrachlorocyclohexane 44 259, 260, 303, 308, 376, 428, 429, 445 Dibutyl adipate, properties and uses - definition 3 123, 124 Dehydroacetic acid, properties and uses N,N-Dibutyl-4-chlorobenzenesulfonamide, 400,401 see W ARF anti resistant - acid, synthesis 400, 401 O,O-Dibutyl 0-2,2-dichlorovinyl Delnav, see phosphate 311 Demeton, analytical method 344 Dibutyl phthalate, properties and uses 142 isomer rearrangement 344 Dibutyl succinate, properties and uses 123 isomers 343 - succinate, synthesis 123 metabolism 344, 345 Dibutyltin dilaurate and maleate 299 oxidation products 345 Dicamba, properties and uses 48, 49, 147 permissible concentration in air 343 - synthesis 147 persistence 345 Dicapthon, properties and uses 331, 332 properties and uses 343-346, 348, 353 - synthesis 331, 332 synthesis 345, 346 Dichlone, properties and uses, 115, 116 Demeton sulfonium compounds 344 - synthesis 116 Dephosphorylation 304 Dichloralurea, properties and uses Desiccants 3, 5, 95, 105, 107, 122, 18,226,228 178-181,252, 393, 407 - synthesis 228 - definition 3 Dichloran, properties and uses 87 Desmethyl Gardona 315 - synthesis 87 Desmetryne, properties and uses 437 Dichloroacetaldehyde 310, 382 Dessin, see Dinobuton Dichloroacetic acid 241 DETA, see Deet Dichloroacetoacetic acid, synthesis 314 Dexon, properties and uses 281 S-2,3-Dichloroallyl N,N -diisopropylthio- - synthesis 281 carbamate, see Di-allate DFDT, persistence 76 2,5-Dichloro-3-aminobenzoic acid, - properties and uses 76 see Amiben - synthesis 76 Dichloroaniline 83, 124, 231 Di-allate, decomposition 210 3,4-Dichlorobenzenediazothiourea, properties and uses 210 see Chloropromurite - synthesis 211 Dichlorobenzenes 67, 68 458 Subject Index

Dichlorobenzhydrol 91 Dichlorophenoxyaniline 109 2,6-Dichlorobenzonitrile, properties and Dichlorophenoxybutyric acid, see 2,4-DB uses 144, 145 5,6-Dichloro-1-phenoxycarbonyl-2-tri - - synthesis 144, 145 fluoromethylbenzimidazole, Dichlorobenzyl alcohol 196 see Fenzaflor 3,4-Dichlorobenzyl N -methylcarbamate, 2,4-Dichlorophenoxyethanol, properties and see Romate uses 108 Dichlorobromoacetic acid 311 - synthesis 180 2,5-Dichloro-4-bromophenol, synthesis 335 Dichlorophenoxyfluoroacetic acids 159 Dichlorobutane 35 Dichlorophenoxypropionic acid 173 Dichlorobutylene 260 2,4-Dichlorophenyl benzenesulfonate, Dichlorobutyne 41 see Genite 2,4-Dichloro-6-( o-chlorophenylamino )-5- Dichlorophenyldimethylurea 234 triazine, see Dyrene Dichlorophenyl isocyanate 231, 232, 235 Dichlorocyclohexadiene 46 N -3,4-Dichlorophenyl-N'-methyl-N'- Dichlorodiethyl ether 107 butylurea, see Neburon Dichlorodimethyl ether 107 N -3,4-Dichlorophenyl-N'-methyl-N'­ 1,8-Dichloro-3,6-dinitrocarbazole 398 methoxyurea, see Linuron 2,3-Dichloro-l ,4-dioxane 374 2,4-Dichlorophenyl-4' -nitrophenyl ether, 4,4' -Dichlorodiphenyl disulfide, see TOK E-25 see Mikazin 2,6-Dichloro-4-phenylpyridine­ Dichlorodiphenylethane 75 dicarbonitrile-3,5, see Pyridinitrile Dichlorodiphenylethynylcarbinol 92 1,2-Dichloropropane, permissible Dichlorodiphenylmethylcarbinol 281 concentration in air 38 1,2-Dichloroethane, explosive properties 38 - properties and uses 35, 38, 39 permissible concentration in air 38 - synthesis 38 - properties and uses 35, 36, 38, 276 1,3-Dichloropropene, permissible - synthesis 38 concentration in air 39 2,5-Dichlorohydroquinone dimethyl ether - properties and uses 35, 39 110 - synthesis 39 Dichloroisobutylenes 40 Dichloropropenes 35, 39 Dichloroisobutyric acid, properties and 3,4-Dichloropropionanilide, see Propanide uses 119, 122 Dichloropropionic acid, see Dalapon - acid, synthesis 122 Dichloropropylene 260 Dichloromethoxybenzoic acid 176 Dichlorosalicylanilide, properties and uses Dichloromethylphenol 170 149 2,4-Dichloro-5-methylphenoxyacetic acid - synthesis 148 158, 161, 172 3,4-Dichlorotetrahydrothiophene dioxide, 1,3-Dichloro-2-methylpropene 40 properties, synthesis, and uses 398 2,3-Dichloronaphthoquine-1,4, see Dichlone 2,6-Dichlorothiobenzamide, see Prefix Dichloronitroaniline, see Dichloran 2,5-Dichlorothiophenol, synthesis 366 Dichloronitrobenzene 124, 125 Dichlorotolan 76 2,5-Dichloro-3-nitrobenzoic acid, 4,5-Dichloro-2-trifluoromethyl- see Dinoben benzimidazole, see Chlorflurazole Dichloronitrophenoxyacetic acids 164 Dichlorvos, persistence 310 5,2' -Dichloro-4'-nitrosalicylanilide, - properties and uses 310, 311, 382, 383 properties and uses 149 - stabilization 311 2,4-Dichlorophenol, dissociation constant - synthesis 310 309 Dicloran, see Dichloran - properties and uses 273, 274, 332 Dicofol, properties and uses 92 - synthesis 335 - synthesis 92 Dichlorophenols 48, 49, 103, 166, 270, Dicoumarol, properties and uses 403 334, 335 - synthesis 403 Dichlorophenoxyacetamides 165 Dicryl, properties and uses 125 3,4-Dichlorophenoxyacetic acid 161 DID 139, 401 Dichlorophenoxyacetic acids 157 ff., 172 Dieldrin, permissible concentration in air 63 Subject Index 459

Dieldrin, properties and uses 42, 53, Diethyl mercury, synthesis and uses 61-63,216, 396 287, 288 - synthesis 63 0,0-Diethy I S -( N -me thy 1-N -carboethoxy­ - tolerances 63 carbamoylmethyl) dithiophosphate, O,O-Diethyl S-benzyl thiophosphate, see Mecarbam see Kitazin O,O-Diethyl 0-( 4-methylcoumarinyl-7) O,O-Diethyl S-carboethoxymethyl thiophosphate, see Potasan dithiophosphate, see Acethion O,O-Diethyl O-p-(methylsufinyl)phenyl O,O-Diethyl S-carboethoxymethyl thiophosphate, see Fensulfothion thiophosphate, see Acetophos O,O-Diethyl 0-4-nitrophenyl phosphate, O,O-Diethyl S-(6-chlorobenzoxazolinyl- see 3-methyl) dithiophosphate, see O,O-Diethyl 0-4-nitrophenyl thiophos­ 0,0-Diethyl S -( 6-chlorobenzoxazolinyl- phate, see 3-methyl) thiophosphate 371 Di-(4-ethylnonyl)amine 83 0,0-DiethyI0-[2-chloro-l-(2',4'­ O,O-Diethyl phthalimidothiophosphate, dichlorophenyl)vinylJ phosphate, properties and uses 353 see Birlane O,O-Diethyl O-pyrazinyl thiophosphate, O,O-Diethyl 0-(3-chloro-4-methyl­ see Thionazin coumarinyl-7) thiophosphate, O,O-Diethyl 0-(3,4-tetramethylene- see Coumaphos coumarinyl-7) thiophosphate, see Dition O,O-Diethyl S-( 4-chloropheny lthiomethyl) Diethyltin dichloride 298 dithiophosphate, see Carbophenothion Diethyl-m-toluamide, see Deet Diethyl chlorothiophosphate, synthesis 326 0,0-DiethyI0-2,4,5-trichlorophenyl O,O-Diethyl 0-(2,2-dichloro-l-ji'-chloro­ thiophosphate 335 ethoxyvinyl) phosphate, see Phosthenon O,O-Diethyl 0-3,5,6-trichloropyridyl O,O-Diethyl 0-2,5-dichloro-4-iodophenyl thiophosphate, see Dursban thiophosphate, see Iodophos-ethyl Difluoran 108 O,O-Diethyl S-(2,5-dichlorophenylthio­ Difolatan, properties and uses 249 methyl) dithiophosphate, - synthesis 249 see Phenka pton Difonate, properties and uses 385 O,O-Diethyl 0-2,4-dichlorophenyl 2,3 -Dihydro-5-carboxanilido-6-methy1-1,4- thiophosphate, see N emacide oxathiin, see Vita vax O,O-Diethyl S-(2-diethylaminoethyl) 2,3-Dihydro-5-carboxanilido-6-methy1-1,4- thiophosphate, see Tetram oxathiin-4,4-dioxide, see Plantvax O,O-Diethyl S-(1,4-dioxenyl) dithiophos­ N -( 5,6-Dihydrodicyclopentadieny1-5)­ phate 373 N',N'-dimethylurea 226, 230 O,O-Diethyl N-l,3-dithioanyl-2-imino Dihydroheptachlor 42, 59 phosphate, see Dithiolane 2,2' -Dihydroxy-5,5' -dichlorodiphenyl­ O,O-Diethyl S-(2-ethylmercaptoethyl) methane, properties, synthesis, and uses dithiophosphate, see Disulfoton 107 O,O-Diethyl 2-ethylmercaptoethyl 4,4' -Dihydroxyphenyl sulfide 338 thiophosphate, see Demeton 3,5-Diiodo-4-hydroxybenzonitrile, O,O-Diethyl S-(2-ethylsulfinyl) see Ioxynil dithiophosphate 369 O,O-Diisopropyl S-(2-benzenesulfamido­ 0,0-DiethyI0-2-ethylsulfonylethyl ethyl) dithiophosphate, see Compound thiophosphate 344 R-4461 O,O-Diethyl S-(ethylthiomethyl) O,O-Diisopropyl S-benzyl thiophosphate, dithiophosphate, see see Kitazin P Diethyl fluorophosphate 379 0,0-Diisopropy I S -( ethy Isulfony Imethy I) O,O-Diethyl (l-hydroxy-2,2,2-trichloro­ dithiophosphate, see Aphidan ethyl) phosphonate 383 O,O-Diisopropyl 0-4-nitrophenyl O,O-Diethyl S-(N-isopropylcarbamoyl­ thiophosphate 304 methyl) dithiophosphate, see FAC 20 N,N' -Diisopropylphosphorodiamidic O,O-Diethyl 0-(2-isopropyl-4-methyl­ fluoride, see pyrimidyl-6) thiophosphate, Dilan, analytical method 80 see Diazinon - persistence 80 460 Subject Index

Dilan, photodecomposition 80 N,N -Dimethyl-N'-4-chloropheny 1- N' - - properties and uses 80, 81 trichloromethylthiosulfamide, synthesis - synthesis 80 and uses 263, 264 Diluents for dusts 14, 15 O,O-Dimethyl 0-4-cyanophenyl thio­ Dimedon 196 phosphate, see Cyanox , properties and uses 316 O,O-Dimethyl S-( 4,6-diamino-1 ,3,5- - syntheses 316 triazinyl-2-methyl) dithiophosphate, Dimelone, see Dimethyl carbate see Menazon Dimetan, analytical method 196 O,O-Dimethyl S-1,2-dicarboethoxyethyl - properties and uses 196 dithiophosphate, see Malathion - synthesis 196 O,O-Dimethyl S-1,2-dicarboethoxyethyl Dimethirimol, properties and uses 423 thiophosphate 355 Dimethoate isomerization 360 0,0-DimethyI0-2,5-dichloro-4-bromo­ - metabolism 360, 361 phenyl thiophosphate, see Bromophos - persistence 361 0,0-DimethyI0-2,2-dichloro-1,2-dibromo­ - properties and uses 355, 359-364 ethyl phosphate, see Naled - stability 361, 362 0,0-DimethyI0-2,5-dichloro-4-iodophenyl - syntheses 361, 362 thiophosphate, see Iodophos Dimethoate oxon, synthesis 360 0,0-DimethyIO-(2,2-dichlorovinyl) Dimethrin, properties and uses 131 If. phosphate, see Dichlorvos O,O-Dimethyl S-2-(acetylamido)ethyl 2,2-Dimethyl-2,3-dihydrobenzofuranyl-7 N­ dithiophosphate, see Amophos methylcarbamate, see Furodan Dimethylalkylhydrazonium salts 282 O,O-Dimethyl S-(3,4-dihydro-4-keto-1 ,2,3- 4-(N,N-Dimethylamino)-3,5-dimethyl­ benzotriazinyl-3-methyl) dithiophos­ phenyl N'-methylcarbamate, see Zectran phate, see Azinphos methyl 2-Dimethylamino-4-hydroxy-5-n-butyl- 5,5-DimethyldihydroresorcinyI N ,N­ 6-methylpyrimidine, see Dimethirimol dimethylcarbamate, see Dimetan O,O-DimethyIO-(N,N-dimethylcarbamoyl- 4-Dimethylaminothiocyanobenzene, 1-methylvinyl) phosphate, see Bidrin see Defoliant 2929 RP 4-Dimethylamino-3-tolyl N-methyl­ Dimethyldiphenylacetamide, carbamate, see Matacil see Diphenamid 1,1'-Dimethyl-4,4' -dipyridylium chloride, Di-(3-methylamyl)amine 83 see Paraquat 0,0-Dimethyl-(1-butyryl-2,2,2-trichloro­ Dimethyldithiocarbamate salts 217, 218 phenyl) phosphonate, see Butonate O,O-Dimethyl S-(5-ethoxy-1,3,4-thia­ 2-Dimethylcarbamoyl-3-methylpyrazolyl-5 diazolinyl-3-methyl) dithiophosphate dimethylcarbamate, see 372 Dimethyl carbate, properties and uses O,O-Dimethyl S-(N-ethylcarbamoylmethyl) 139,401 dithiophosphate, see Fitios - carbate, synthesis 139 O,O-Dimethyl S-ethylmercaptoethyl 2,2-Dimethyl-6-carbobutoxy-2,3-dihydro­ thiophosphate, see Metasystox-I pyranone-4, see Indalone O,O-Dimethyl 2-ethylmercaptoethyl 0,0-Dimethyl S-(1-carboethoxybenzyl) thiophosphate, see Methyl demeton dithiophosphate, see Cidial O,O-Dimethyl S-(2-ethylmercaptoethyl) O,O-Dimethyl S-carboethoxymethyl dithiophosphate, see Thiometon thiophosphate, see Methylacetophos O,O-Dimethyl S-(2-ethylsulfinyl)ethyl 2,4-Dimethyl-5-carboxanilidothiazole, dithiophosphate 369 see G-696 O,O-Dimethyl S-(2-ethylsulfinyl)ethyl O,O-Dimethyl S-(carboxymethyl) dithio­ thiophosphate, see Oxydemetonmethyl phosphate 363 O,O-Dimethyl S-[2-(ethylsulfinyl)iso­ O,O-Dimethyl 0-(2-chloro-2-N,N-diethyl­ propy I] thiophosphate, see Metasystox-S carbamoyl-1-methylvinyl) phosphate, 0,0-Dimethyl (1-hydroxy-2,2,2-trichloro­ see ethyl) phosphonate, see Trichlorfon 0,0-DimethyI2-chloro-4-nitrophenyl O,O-Dimethyl N-(isopropoxycarbamoyl) thiophosphate, see Dicapthon phosphate, see A venin Subject Index 461

O,O-Dimethyl S-(N-isopropylcarbamoyl­ 3,4-Dimethylphenyl N-methylcarbamate, methyl) dithiophosphate 362 see MPCM Dimethylmercury 291 Dimethylphosphate of alpha-methylbenzyl- O,O-Dimethyl S-(N -2-methoxyethyl­ 3-hydroxy-cis-crotonate, carbamoylmethyl) dithiophosphate, see Crotoxyphos see Amidithion Dimethyl phosphite, synthesis 36 0,0-Dimethyl S -( 5-methoxypyrony1- 2- Dimethyl phthalate 139, 142, 151, 401 methyl) thiophosphate, see O,O-Dimethyl S-(N-phthalimidomethyl) O,O-Dimethyl S-(5-methoxy-1,3,4- dithiophosphate, see Imidan thiadiazolinyl-3-methyl) dithio­ Dimethyl tetrachloroterephthalate, phosphate 372 see Dacthal O,O-Dimethyl S-2-(1-methylcarbamoyl­ Dimethyl tetrachlorothioterephthalate, ethylmercapto)ethyl thiophosphate, see Glenbar see Vamidothion 3,5-Dimethy1-1,2,3,5 -tetrah ydro-1 ,3,5- thiadiazinethione-2, see Thiazone O,O-Dimethyl S-(N -methylcarbamoyl­ N,N-Dimethyl-4-thiocyanoaniline 254, 259 methyl) dithiophosphate, Dimethylthiourea 430, 431 see Dimethoate Dimethylthiuram disulfide, see Tridipam O,S-Dimethyl S-(N-methylcarbamoyl­ O,O-Dimethyl 0-2,4,5-trichlorophenyl methyl) dithiophosphate 360 thiophosphate, see Ronnel O,O-Dimethyl S-(N-methylcarbamoyl­ Dimethylxanthogen disulfide 180 methyl) thiophosphate 360 Dimetilan 188, 197 0,0-DimethyIO-(1-methyl-2-carbo­ Dimite, properties and uses 91, 92 methoxyvinyl) phosphate, - stability 91 see - synthesis 91 O,O-Dimethyl S-(N-methyl-N-formyl­ Dinex, properties and uses 101 carbamoyl methyl) dithiophosphate, - synthesis 101 see Formothion Dinitroalkylphenols 93, 178 0,0-DimethyI2-methylmercaptoethyl Dinitro-sec-amylphenol 100 thiophosphate, see Tinox Dinitroanisole 108 O,O-Dimethyl 0-(4-methylmercapto-3- Dinitro-sec-butylphenol, see Dinoseb methylphenyl) thiophosphate, Dinitrochlorobenzene 258, 259 see Fenthion Dinitro-o-cresol, see DNOC 0,0-DimethyIO-4-methylmercaptophenyl Dinitrocyclohexylphenol, see Dinex thiophosphate and oxon 337 Dinitro-sec-octylphenyl crotonate, N,N -Dimethyl-N'-3-methylphenyl­ see Dinocap thiourea, see Methiuron 2,4-Dinitrophenol, explosive properties O,O-Dimethyl S-(morpholinocarbamoyl­ 97 methyl) dithiophosphate, - properties and uses 97, 389 see Morphothion - synthesis 97 O,O-Dimethyl 0-4-nitro-3-chlorophenyl Dinitrophenols 93, 177 thiophosphate, see Chlorthion 2,4-Dinitrothiocyanobenzene, see DNTB 0,0-DimethyI0-4-nitrO-3-methylphenyl Dinoben, properties and uses 147, 148 thiophosphate, see - synthesis 148 0,0-DimethyI0-6-nitro-3-methylphenyl Dinobuton, properties and uses 100 thiophosphate 330, 331 - synthesis 100 0,0-DimethylO-4-nitrophenyl thio­ DINOC, see DNOC phosphate, see Methyl parathion Dinocap, properties and uses 97, 101, 102 O,O-Dimethyl S-4-nitrophenyl thiophos­ - synthesis 101 phate 328 Dinocton-o 100 0,s-DimethylO-4-nitrophenyl thiophos­ Dinocton-p 101 ph ate 328 Dinofen, see Dinibuton 3,5-Dimethyl-4-nitrosopyrazoles, synthesis Dinoseb, properties and uses, 98-101 415 - syntheses 99 N,N -Dimethyl-N' -phenyl-N' -fluoro­ Dinoseb methacrylate 100 dichloromethylthiosulfamide, see Eparen Dinoterb-acetate 100 462 Subject Index

Di-n-octylamine 83 Dithiolane, properties and uses 318 Dioctylbenzotriazolium chloride 427, 428 - synthesis 318 1,4-Dioxane-2,3-S,S'-bis(O,O-diethyldithio- Dithiophosphoric acid derivatives, pesti- phosphate, see Dioxathion cidal properties 354 ff. Dioxathion, isomers 373 - acid esters, syntheses 356 ff. properties and uses 373, 374 Dithiophosphoric acids, synthesis 357 - stability 373 Dithiosystox, see Disulfoton - syntheses 373, 374 Dition, properties and uses 341 Dioxathion oxon 373 - synthesis 341 2-(1,3-Dioxolanyl-2)phenyl N -methyl- Diuron, synthesis 231 carbamate, see C 8353 DMSA 127 1, l'-Di(pentamethylenecarbamoylmethyl)- DN compounds, see specific compounds 4,4' -dipyridylium chloride, see PP-407 DNOC, explosive properties 97 Diphenamid 144, 155 metabolism 97, 98 Diphenatrile 155 permissible concentration in air 98 Diphenyl, see Biphenyl properties and uses 97, 98, 101 Diphenylacetonitrile, see Diphenatrile synthesis 98 Diphenylamine as 83 DNTB, explosive properties 259 Diphenyldiimide, see Azobenzene permissible concentration in air 259 Diphenylmercury 295 - properties and uses 254, 259 Diphenyl sui fones, properties and uses - synthesis 259 243-245 Dodecylguanidine acetate, see Dodine - sulfones, synthesis 245 Dodecylguanidine tetrahydrophthalate 239 Diphosgene 178 Dodecyl thiocyanate 253 O,O-DipropyIO-2,2-dichlorovinyl Dodine properties and uses 228, 238, 239 phosphate 311 - stability 238 Dipropyl isocinchomeronate, properties, Dorlone 39 synthesis, and uses 403 Dormancy breaker 252 Dipterex, see Trichlorfon Dowco-l09 321 Dipyridyls, synthesis 407 Dow ET-14 and ET-57, see Ronnel Dipyrrolidylthiuram disulfide, see DPDT Dowfumes B-85 and EB-5 38 Diquat, properties and uses 409 Dowicide-A 95 - synthesis 409 DPDT, synthesis 222 Disodium ethylenebis( dithiocarbamate), DPS, see Diphenyl sulfone see Nabam duPont fungicide 328, properties and Dispersed spraying 23 uses 432 Disulfoton, metabolism 368 - fungicide 328, synthesis 432 properties and uses 367-369 - fungicide 1991, see Benlate - sulfonium compounds 368 Dursban, properties and uses 321, 339, 340 - syntheses 369 - synthesis 339, 340 Di-Syston, see Disulfoton Dursban oxon 339 Dithanes C-31 and M-45 222 Dusts 12 ff. 1,4-Dithiaanthraquinone-2,3-dinitrile, Dylox, see Trichlorfon see Dithianon Dyrene 433 Dithianon 425 Dithiocarbamates 216, 217 E-236424 Dithiocarbamic acid esters, pesticidal E-605, see Parathion properties 222 ff. E-838, see Potasan - acid salts, syntheses 211 ff. EDB 409 Dithiocarbamic acids, pesticidal properties Eggs 215 206 ff. Ekatin, see Thiometon Dithiocarbonic acids, pesticidal properties Ekatin-F and -M, see Morphothion 177 ff. EMMI, properties and uses 288, 289 - acids, synthesis 179 ff. - synthesis 289 Dithiocyanoethane 253 Emulsifiers 22 Dithiocyanomethane 253 E~ulsive concentrates 12, 21 ff. Subject Index 463

Enanthic aldehyde 111 Ethylenebis( di thiocarbama tes), pesticidal Encapsulated insecticides 25 properties 218 Endoif 200 Ethylenebis(dithiocarbamic) acid salts , properties and uses 267, 268, 217-219,254 428 E thy lene bis (3-methy Itetrahydro-l, 3,5- - stability 267 thiadiazinethion-2-yl-5) 430 - synthesis 267, 268 3,3' -Ethylenebis( tetrahydro-4,6-dimethyl- Endosulfan-alcohol, synthesis 267 2 H -1 ,3,5-thiadiazine-2-thione), Endothall 200 see duPont fungicide .328 Endothion, metabolism 343 Ethylenebis(thiuram polysulfide), - properties and uses 343 see Poly ram - synthesis 343 Ethylene chlorohydrin 90, 91 , properties and uses 42, 53, 63 ff., 1,1'-Ethylene-2,2-dipyridylium bromide, 396 see Diquat stabilization 64 Ethylene oxide 396 syn thesis 64 Ethylene sulfide 396 tolerance 64 S-Ethyl hexahydro-l H-azepine-l-carbo­ Endrin ketone 64 thioate, see Molinate ENT-21486, see Siglure 2-Ethylhexanediol-l,3, synthesis and uses Enzymes and pesticides 7 90, 401 Eparen, properties and uses 264 2-Ethylhexylimide of bicyclo [2.2.1] heptene­ - synthesis 264 dicarboxylic acid, properties and uses 139 EPN, properties and uses 384 Ethyleneimine 396 - synthesis 384 N -E thy Imercuri -3, 4,5,6,7,7 -hexachloro-3 ,6- - tolerance 384 endometh y lene-l ,2,3 ,6-tetrahydro­ Eptam, see EPTC phthalimide, see EMMI EPTC, decomposition 209 N -(E thylmercuri)-p-toluenesulfonanilide, - properties and uses 209 see Ceresan-M - synthesis 209 Ethylmercury acetate 290 Eradex, properties and uses 182 Ethylmercury chloride, permissible con­ - synthesis 182 centration in air 287 Eradex-S-oxides 182 - chloride, synthesis and uses 50, 69, 285, Erbon 108, 121, 122 287, 290, 292, 295 Esters, pesticidal properties 122 ff. Ethylmercury phosphate, permissible Ester sulfonate, see Ovex concentration in air 288 Ethanesulfonyl fluoride 276 - phosphate, synthesis and uses 19, Ethers, pesticidal properties 107 ff. 287-289 , properties and uses 364, 367 Ethylmercury sulfate 286, 288 - synthesis 367 O-Ethyl 0-(4-methylcoumarinyl-7) thio­ Ethoxynol, properties and uses 92 phosphoric acid 340 Ethrel, mode of action 384 O-Ethyl S-methyl O-nitrophenyl thiophos­ - properties and uses 384, 385 phate 329 - stability 384 O-Ethyl 0-(4-nitrophenyl) benzenethio­ O-Ethyl O,O-bis( 4-nitrophenyl) thio­ phosphonate, see EPN phosphate 326 O-Ethyl 0-( 4-nitrophenyl) n-hexylthio­ Ethyl bromide 35 phosphonate 381 O-Ethyl 0-2,4-dichlorophenyl benzenethio­ O-Ethyl 0-( 4-nitrophenyl) isopropylthio­ phosphonate 384 phosphonate 381 Ethyl dimethyldithiocarbamate, O-Ethyl 0-(4-nitrophenyl) methylthio­ see Compound No. 23 phosphonate 381 O-Ethyl S,S-diphenyl dithiophosphate, O-Ethyl S-phenyl N-butylamidodithio­ see Hinosan phosphate, see Phosbutyl S-Ethyl N,N-di-n-propylthiocarbamate, O-Ethyl S-phenyl ethyldithiophosphonate see EPTC see Difonate Ethylene, defoliant action 2(, Ethyltin trichloride 298 464 Subject Index

O-EthyIO-2,4,5-trichlorophenyl ethylthio- Fluorobromodinitrobenzene 81 phosphonate, see Fluorodinitrobenzene and amino acids Etrolene, see Ronnel 81,82 Eulan-AVA 275 Fluoroethyl esters of phenylphenylacetic Eulan-BL 275 acid, pesticidal properties 142 Eulan-CN, synthesis 270 Fluoroethylformal 108 Eulan-N, synthesis 270 Fluoronitrobenzenes 81 Eulan-SN 270 Fluoroparacide, properties and uses 241 Evaporation inhibitors 22 - synthesis 241 - of drops 8 If. Fluoroparacide sulfoxide and sulfone 241 Fluorophenoxyacetic acid 172 4-Fluorophenyl-4'-chlorobenzyl sulfide, FAC 20, properties and uses 362 see Fluoroparacide - synthesis 362 Falone, properties and uses 307, 308 Fluorosulfacide, see Fluoroparacide - synthesis 308 Fluorothiophenol, synthesis 242 Fenac, properties and uses 144, 153 5 -Fluorouracil 439 - syntheses 153, 154 5-Fluorouracilcarboxylic acid 439 Fluosilicates, pesticidal properties 444 Fenchyl thiocyanoacetate 254 FMA, see Ceresan Fenidim, see Fenuron Folex, see Merphos Fenitrothion, explosive hazard 330 - properties and uses 330, 331, 337 Folic acid derivatives, pesticidal properties 439 - synthesis 330 Fenson, properties and uses 271, 274 Folidol-80, see Methyl parathion Folithion, see Fenitrothion - synthesis 274 Folpet 240, 248, 249 Fensulfothion, properties and uses 337, 338 Folsan 82 - syntheses 337, 338 Fenthion, persistence 336 Food control laboratories, U.S.S.R. 6 Formaldehyde, properties and uses - properties and uses 336, 337 111,370-372,430,431,443 - synthesis 336, 337 - stabilization 111 Fenthion sulfoxide and sulfone 336 Fenthiuram 104, 216 Formamidines 129 Fenthiuram-molybdate 104,216 Formative elfect 427 Fenuron, analytical method 230 Formothion, metabolism 363 - properties and uses 226, 230, 231 - properties and uses 363, 364 - synthesis 231 - synthesis 364 Fenzaflor, properties and uses 418 Formulations of pesticides 9, 12 If., 175 If. Ferbam, properties and uses 213, 215 4a-Formy 1-1 ,4,4a,5a,6, 9, 9a, 9b-octahydro- - stability 215 dibenzofuran, properties, synthesis, - synthesis 215 and uses 397 Fermate, see Ferbam 1-Formyl-l ,2,3,4-tetrahydroquinoline, Film-forming agents 17 see Kyuzol Fitios, properties and uses 362 Freons 20, 24, 36, 241, 256 - synthesis 362 Frescon 424 Flax 1, 98, 125, 147, 171, 175,209-211, Fumazone 39 282,438 Fumigants (see also specific compounds) Fluometuron, properties and uses 232, 233 12, 25, 35, 177, 178, 181, 240, 276, 396, - syntheses 233 441 Fluoride salts, pesticidal properties 444 definition 3 Fluorine analogs of chlordane 59 Fundal 129 - analogs of 59 Fungicides, definition 3 Fluoroacetamide 119 - systemic 4 Fluoracetanilide 119 Fungilon, properties and uses 417, 418 Fluoroacetic acid, mode of action 119 - synthesis 417 - acid, properties and uses 118, 119 Fungus control 27, 30, 40, 68, 69, 81, 82, - acid, synthesis 119 93 If., 108, 111, 115 If., 124, 130, 142, Fluoroalkylcarboxylic acids, toxicities 118 148 If., 157 If., 176, 182,207,213 If., Subject Index 465

225, 227, 228, 238-240, 247 If., 252 If., Guanidine and derivatives, pesticidal 263 If., 269, 276, 278, 283 If., 297 If., properties 225, 238 If. 321, 352-354, 356, 375, 380, 387, Gusathion, see Azinphos methyl 390 If., 396 If., 400, 405, 409 If., 414 If., Gusathion-A, see Azinphos ethyl 426, 427, 430 If., 441 If., 445 Guthion, see Azinphos methyl Furan 396 Gyplure, properties and synthesis 89 Furethrin 131 If. Furfuralacetone 397 Furidazol, properties and uses 418 Furodan 192 H-22 191 2-(2-Furyl)benzimidazole, see Furidazol H-28191 Fusarex 82 Haloacetic acids, pesticidal properties 118 Halobenzils, pesticidal properties 67 Halodinitrophenols, pesticidal properties 95 Halofumaric acids, pesticidal properties G-4 107 124 G-696, properties and uses 419 Halogen compounds, pesticidal properties - synthesis 419 443 If. Gardona analogs 315 Halogenated alicyclic compounds, pesticidal persistence 315 properties 42 If. - properties and uses 315 Halogenated aliphatic compounds, - synthesis 315 see specific compounds Garlic 200 aliphatic compounds, pesticidal proper­ Garnitan, see Linuron ties 34 If. GC-7787, see Hexafluoroacetone aliphatic compounds, structure-activity Genite, properties and uses 271, 273, 274 relationships 35 - synthesis 274 Halogenated aromatic compounds, Germisan 293, 295 pesticidal properties 67 If. Gesaran, properties and uses 437, 438 Halomethylphenoxyacetic acids as - synthesis 438 herbicides 158 Gibberellic acid 137 Halonaphthalenes, pesticidal properties Gibberellins, action on plants 137, 138 67,6S analogs 138 Halonitro compounds, biological action 78 - properties and uses 130, 136 If., 398 Halophenols, pesticidal properties 102 If. - stability 138 Hanane, see Dimefox Gladiolas 226, 232, 292 HCCH, see BHC Glenbar, properties and uses 153 Heavy oil 31 Glucochloralose, properties and uses 117 Hempa 318 Glyfluor 108 Heptachlor, analytical methods 58 Glyodin, properties and uses 416, 417 dechlorination 58 - synthesis 416, 417 fluorine analogs 59 Grains (see also specific kinds) 27, 37, 68, permissible concentration in air 59 69,98, 111, 128, 147, 149, 161, 169, persistence as epoxide 59 173, 176,221, 222, 260, 263, 269, 290, properties and uses 42, 53, 56 if., 59, 292,294,339, 394, 408, 411, 437, 438, 69, 1Q4, 216 446 synthesis 57 pest-caused losses 5 tolerances 59 Granosan 19,287, 394 Heptachlor epoxide 59 Granules 12, 15 If. Heptachlorocyclohexane 44, 47 Grapes and vines 35, 36, 40, 55, 138, 222, Heptachloropropane 35 247,249, 259 2-Heptadecylimidazoline acetate, - pest-caused losses 5 see Glyodin Grasses 125, 153, 206, 232, 418, 439 Herban, see Norea Green oil 29 Herbicides, definitions 3-5 Growth regulators 3, 5, 14, 112, 136, 154, nonselective 4 157 If., 172 If., 206, 207, 225, 259, 282, root or seed alfecting 4, 5 384, 396, 398-400, 428 selective 4 466 Subject Index

Herbicides, wetting agents and mode of Hydram, see Molinate action 175 if. Hydrazine derivatives, pesticidal properties Herbisan 180 278 if. Heteroauxin, properties and uses 398, 399 Hydrazobenzene 278 - syntheses 399 Hydrocarbons, pesticidal properties 26, 27 Heterocyclic compounds, pesticidal Hydrogen cyanide 37, 240, 252, 255, 284, properties 396 if., 413 if., 427 if. 291, 399 Hexabromobenzene 68 Hydrogen phosphide, see Phosphine Hexachloroacetone, permissible concen- Hydrogen sulfide 37, 214, 215, 284, 369, tration in air 112 377, 392 - properties and uses 112 Hydrol, see APe - synthesis 112 H ydroxybenzoic acids, pesticidal properties Hexachlorobenzene, permissible concen­ 142, 148 if. tration in air 69 Hydroxybenzonitrile, synthesis 150 properties and uses 46-50, 55, 67-69, 2-Hydroxy-4,6-bis( ethylamino)-s-triazine 96, 106, 418 435 synthesis 68 Hydroxychlordene 58 1,2,3,4,7,7 -Hexachlorobicyclo [2.2.1] hep­ 4-Hydroxycoumarin, synthesis 402 tene-2,5,6-bis(methylene) sulfite, 2-Hydroxydiethyl sulfide 347 see Endosulfan Hydroxydiphenyl, properties and uses 1,2,3,4,7,7 -Hexachloro-5,6-bis( chloro­ 94-96 methyl)-bicyclo [2.2.1] heptene-2, - synthesis 95 see Alodan 1-Hydroxyethyl-2-heptadecylimidazoline, Hexachlorobutadiene, properties and uses synthesis and uses 417 35,40, 55 3-Hydroxypyridazone, see Maleic hydrazide - synthesis 40 8-Hydroxyquinoline, see Oxine Hexachlorocyclohexenone 48 Hyvar, see Bromacil Hexachlorocyclopentadiene, properties and synthesis 53 if. Imidan, persistence 370 Hexachlorodihydroxydiphenylmethane - properties and uses 370, 371 48, 49 - synthesis 370, 371 Hexachloroethane, properties and uses 38 Imidazolidinone-2, properties, synthesis, - synthesis 38 and uses 415 Hexachloromethylcyclohexanes 43 Imidazoline salts 415 Hexachlorophene, properties and uses 103 Imides, pesticidal properties 124 if. - synthesis 107 Iminophosphate, see Dithiolane Hexachlorophenols, pesticidal properties Indalone, properties and uses 139, 401 105 - synthesis 401 Hexachloropropene 35 3-Indolylacetaldehyde 112, 399 Hexadecadienol and acetate 89 3-Indolylacetic acid, see Heteroauxin Hexadecyl thiocyanate 253 3-Indolylacetonitrile 399 Hexafluoroacetone 112 3-Indolyl-r-butyric acid, properties, Hexagamma, see Hexachlorobenzene synthesis, and uses 159, 399, 400 Hexakis( l-aziridiny I) phosphoni trile 318 Inferno, see Tetram Hexamethylenebenzamide, see Benzimine Insect-borne diseases 2 Hexamethyl triamidophosphate 318 Insecticidal smokes 23 Hexylamine 83 Insecticides, definitions 3 Hexyl thiocyanate 253 - in capsules 25 Hinosan, properties and uses 375 Insects, damaging species 1 - synthesis 375 - penetration by insecticides 3 HMPA 318 Intrathion, see Thiometon Hops 316 Inverted emulsions 22 House fly reproductive rate 2 Iodoaniline 83 HS-14260 438 Iodophos 335, 336 H ydantoins, properties and syntheses Iodophos-ethyl 335, 336 233, 234 Ioxynil, properties and uses 144, 149, 150 Subject Index 467

Ioxynil, synthesis 150 Lauric acid, pesticidal properties 118 Ioxynil caprylate 150 Lawns 147, 152, 155, 294, 353 Ipazine 437 Lead arsenate 388 IPC, see Propham Lead compounds 286 Irish potato famine 1 Leather, protection 1, 81 Iron dimethyldithiocarbamate, see Ferbam Lebaycid, see Fenthion , properties and uses 397, 398 Lenacil, properties and uses 421, 422 Isobornyl thiocyanoacetate 257 - synthesis 422 Isocyanatophosphoric acid 317 Lentils 210 Isodrin, oxidation 64 Lethane 60, properties and uses 257 - properties and uses 42, 53, 63 - 60, synthesis 257 - synthesis 63 Lethane 384, properties and uses 253, 256 Isolan, properties and uses 188, 196, 197 - 384, synthesis 256, 257 - synthesis 197 Lethane 384, Special 257 Isopestox, see Mipafox Lettuce 76 2-Isopropoxyphenyl N -methylcarbamate, Leutosan 295 see Baygon Lichen control 115 Isopropyl N -acetoxy-N -phenylcarbamate, Light oil 31 see Acylate Limacides, definition 3 Isopropyl N-(3-chlorophenyl)carbamate, Lime sulfur, properties and uses 441 see Chloropropham , penetration into insects 4 Isopropyl N -( 4-fluorophenyl)carbamate 184 properties and uses 25, 45, 59, 69, 76, 2-Isopropyl-4-methyl-6-hydroxypyrimidine, 340 synthesis 338, 339 separation from BHC 48 if. 1-Isopropy 1-2-methyl pyrazol y 1-5 -dimeth y 1- Linuron, decomposition 234 carbamate, see Isolan - properties and uses 234, 235 Isopropyl N -phenylcarbamate, see Propham -- syntheses 235 3-Isopropylphenyl N-methylcarbamate, Lipsticks 142 see UC-I0854 Lithuram, see DPDT Isothiocyanates, pesticidal properties 252 if. Lovo 22 Isourea compounds 185 Low-volume spraying 10, 19, 24, 28 2-Isovalerialylindandione-l,3 114 Magnesium chlorate 429, 445 K-69-79, see Avenin Magnesium fluosilicate 444 Karathane, see Dinocap Maize (see also Corn) 127,439 Karsil 125 , synthesis 358 Keam 32 Malathion, analytical method 358 Kelthane, see Dicofol explosive hazard 357 Kepone 65 isomerization 357 Kerosine 27 if. metabolism 355 Ketoendrin 64 permissible concentration in air 357 Ketones, pesticidal properties 112 if. properties and uses 303, 304, 357-359 2KF 146 syntheses 358, 359 Kitazin, properties and uses 352 stability 358 - synthesis 352 tolerance 358 Kitazin P 352 Maleic hydrazide, properties and uses Korlan, see Ronnel 419, 420 Krysid, see Antu - hydrazide, synthesis 420 K wiksan, see Ceresan MALS, properties and uses 392 Kyuzol, properties and uses 411 - synthesis 392 - synthesis 411 Maneb, decomposition 221 Kyuzol-A, properties and uses 411, 412 properties and uses 211, 217, 221, 222 - synthesis 411,412 - stabilization 221 - synthesis 221, 222 Langmuir formula 8 Manganese dimethyldithiocarbamate, Lanoate, properties and uses 192 see Marbam 468 Subject Index

Manganese ethylenebis( dithiocarbamate), Mesurol, synthesis 194, 195 see Maneb Metaldehyde 111 Maqbarl, properties and uses 191 Metaphos, see Methyl parathion Marbam 215 Metaphoxide 318 Marine growths, control 390 Metasystox, see Methyl demeton MAS, see Methylarsine sulfide Metasystox-I, properties and uses 348 Matacil, properties and uses 191 - syntheses 348 MB 8882, properties and uses 205 Metasystox-R, see Oxydemetonmethyl 2M-4C, see MCPA Metasystox-S, properties and uses 349 2M-4CB, see MCPB - synthesis 349 2M-4CP, see Mecoprop Metathion, see Fenitrothion MCPA, chlorocresol in 168 Metazol, properties and uses 292 esters 171 - synthesis 292 properties and uses 120, 145, 147, 158, Metepa 318 159, 161, 162, 168-171, 438 Methacrylic acid anilides 125 salts 168 MethaIIyl bromide 35 syntheses 168-170 MethaIIyl chloride, flammability 40 MCPB, cyclization 174 - chloride, properties and uses 35, 40 oxidation 173 - chloride, synthesis 40 - properties and uses 173, 174 Methanesulfonic acid dichloramide, - syntheses 174 synthesis and uses 275 MCPP, see Mecoprop Methanesulfonyl fluoride, permissible Mecarbam, metabolism 364 concentration in air 276 - properties and uses 364 - fluoride, properties and uses 276 - synthesis 364 - fluoride, synthesis 276 Mecoprop, properties and uses 149, 172, Methiotepa 318 173 Methiuron, properties and uses 236, 237 - salts 172, 173 - synthesis 237 - synthesis 173 2-Methoxy-5-acetylbenzaldehyde, Medinoterb-acetate as herbicide 100 properties and uses 112 Medium oil 31 2-Methoxy-4,6-bis( ethyl amino )-s-triazine Medlure 139, 140 435 Melons 423 3-Methoxycarbonylaminophenyl N-3'- MEMMI, properties and uses 292 methylphenylcarbamate, see Betanal - synthesis 292 , dehydrochlorination 76 Menazon, properties and uses 373 - properties and uses 50, 75 if. - synthesis 373 - synthesis 75 Meobal, see MPCM 2-Methoxy-3,6-dichlorobenzoic acid, Mercaptans, pesticidal properties 240 if. see Dicamba Mercaptobenzothiazole 215 2-Methoxy-4-ethylamino-6-isopropyl­ Mercaptophos, see Demeton amino-s-triazine, see Atratone Mercuran 50, 287 Methoxyethylmercuric acetate, synthesis Mercuric chloride 283 292 Mercuric sulfide 285 Methoxyethylmercuric chloride, see Aretan Mercurihexane 69, 287 Methoxyethylmercuric silicate, properties Mercury compounds, pesticidal properties and uses 293 283 if. Methoxyethylmercury compounds 285-287 - compounds, reactions 284, 285 N -4-( 4' -Methoxyphenoxy)phenyl-N',N'- Mergamma 295 dimethylurea, see C-3470 Merphos, properties and uses 308 Methoxytrichlorobenzoic acid 48 - synthesis 308 Methylacetophos, methylating ability 351 Merthiolate 290 - properties and uses 351 Mesulfan, properties and uses 249, 250 - synthesis 351 - stability 250 Methyl acrylate 123 - synthesis 250 Methyl N -( 4-aminobenzenesulfonyl)­ Mesurol, properties and uses 188, 194 carbamate, see Asulam Subject Index 469

Methylarsenic acid and salts 391-393 Methylethyl chlorothiophosphate, synthesis Methylarsine bis( dimethyldithiocarbamate), 329 see Urbazid O-Methyl O-ethyl dithiophosphoric acid, Methylarsine bis(lauryl sulfide), see MALS synthesis 369 Methylarsine oxide 390-393 O-Methyl O-ethyl S-(2-ethylthioethyl) Methylarsine sulfide, properties and uses dithiophosphate, see Tetrathion 391,392 O-Methyl O-ethyl S-(N-methylcarbamoyl­ - sulfide, synthesis 392 methyl) dithiophosphate 355 N -Methyl-N'-(2-benzothiazolyl)urea 227 O-Methyl O-ethyl 0-4-nitrophenyl O-Methyl O,O-bis( 4-nitrophenyl) thiophosphate, see Methylethylparathion thiophosphate 328 O-Methyl S-ethyl 0-4-nitrophenyl Methyl bromide, explosive properties 37 thiophosphate 329 bromide, methylating abilities 37 Methylethylparathion, permissible bromide, permissible concentration concentration in air 328 in air 37 - properties and uses 328, 329 bromide, properties and uses - synthesis 329 35,37, 128,263 Methylethylthiophos, see Methylethyl­ bromide, synthesis 37 -1-(butylcarbamoy1)-2- O-Methyl O-ethyl 0-2,4,5-trichlorophenyl benzimidazole carbamate, see Benlate thiophosphate, see Trichlormetafos-3 3-Methyl-5-carboxymethyltetrahydro-1 ,3,5- Methyl formate 36, 123 thiadiazinethione-2, Methyl isocyanate, properties and uses see Thiadiazinethione 186, 193-196, 198, 236 Methyl chloride, permissible concentration - isocyanate, synthesis 189 in air 36 Methyl isothiocyanate, properties and uses - chloride, properties and uses 36, 37 212,213,255,260,430,431 - chloride, synthesis 36 - isothiocyanate, synthesis 260 O-Methyl 0-2-chloro-4-tert-butylphenyl­ 3 -Meth y lisoxazoledione-4, 5-o-chloro­ N-methylamidophosphate, see Ruelene phenylhydrazone 415 Methyl crotonate 123 Methylmercapto-3,5-dimethylphenol, Methyl demeton, isomerization 346 synthesis 194 demeton, metabolism 346, 347 4-Methylmercapto-3,5-dimethylphenyl demeton, oxidation products 347 N-methylcarbamate, see Mesurol demeton, permissible concentration 4-Methylmercapto-3-methylphenol, in air 346 synthesis 337 demeton, persistence 347 Methylmercaptophos, see Methyl demeton demeton, properties and uses 346-350, Methylmercuric chloride 292 367,368 Methylmercuric cyanide, see Chipcote demeton, stability 346 Methylmercuric hydroxide, synthesis 291 demeton, synergism 347 Methylmercuric sulfate 291 demeton, synthesis 347 Methylmercuridicyanodiamide, Methyldichloroarsine 391, 392 see Panogen O-Methyl 0-2,5-dichloro-4-bromophenyl N -(Methylmercuri)-3,4,5,6,7,7 -hexachloro- phosphoric acid 335 3 ,6-endometh y lene-1 ,2,3,6-tetrahydro­ Methyl N-(3,4-dichlorophenyl)carbamate, phthalimide, see MEMMI see Swep Methylmercury ,8-hydroxyquinolate, O-Methyl 0-2,4-dichlorophenyl N-iso­ see Metazol propylamidothiophosphate, see Zytron O-Methyl S-(5-methoxypyronyl-2-methyl) Methyl dimethyldithiocarbamate, thiophosphate 343 see Cystogon N -Methyl-N'-methyl-N' -(2-benzo­ N-Methyldithiocarbamic acid 206 thiazolyl)urea 227 Methylene-bis(4-chlorophenyl sulfide) 241 Methyl-N-methylcarbamoylbenzenesulfonyl 3,3'-Methylene-bis( 4-hydroxycoumarin), carbamate, see Compound MB-9555 see Dicoumarol 2-Methyl-2-methylthiopropionaldoxime Methylene bromide, toxicity 35 O,N-methylcarbamate, see Aldicarb Methylene chloride, toxicity 35 Methyl naphthylacetate 155 470 Subject Index

Methyl N -(4-nitrobenzenesulfonyl)­ Mipafox, synthesis 316 carbamate, see MB 8882 65 Methylnitrophos, see Fenitrothion Miscible oils 22 Methyl parathion, explosive hazard Mite control 55, 64, 91 If., 129, 141, 176 If., 327,328 182,190 If., 240 If., 252, 266, 269, parathion, methylating ability 327 271 If., 278 If., 307 If., 319 If., 354, parathion, properties and uses 361 If., 380, 384, 415, 418, 441, 442 97, 303, 326-331, 336, 384 Mitin-FF, synthesis 271 parathion, synthesis 328 Mobam 192 Methylphenoxyacetic acid 170 MO Granules 109, 110 1-Methyl-2-phenyl-3-dodecylbenzimidazo­ Molinate, properties and uses 210 linium ferrocyanide, see Fungilon - synthesis 210 3-Methylphenyl N-methylcarbamate, Molluskicides, definition 3 see MTMC Monalide 126 I-Methylpropyn-2-yl N-(m-chlorophenyl)­ Monolinuron 234, 235 carbamate, see Bi-PC Monuron 184,200,204,231, 236 6-Methyl-2,3-quinoxaline dithiocarbonate, Morestan, see Chinomethionate see Chinomethionate Morphothion, properties and uses 363 2-Methylthio-4,6-bis( ethyl amino )-s­ - synthesis 363 triazine 435 Mothproofing, see Wool preservation 2-Methylthio-4,6-bis(isopropylamino)-s- MPCM 190 triazine, see Prometryne MTMC 190 Methyl thiocyanate 260, 435 Mucochloric acid anilides 128 Methyl thiocyanoacetate 254 - acid, properties and syntheses 2-Methylthio-4-ethylamino-6-tert- 397, 420, 421 butylamino-s-triazine, see HS-14260 Mulberries 376, 380 2 -Methyl thio-4-isopropy lamino-6- Murbetol 200 (3-methoxypropylamino)-s-triazine, Murvesco, see Fenson see Gesaran Muscatox, see Coumaphos 2-Methylthio-4-methylamino-6-isopropyl­ Mylone, see Thiazone amino-s-tri azine, see Desmetryne Methyl thiomethylketoxime N-methyl­ Nabam 217, 218 carbamate, see Lanoate Naled, properties and uses 310, 311 O-Methyl 0-2,4,5-trichlorophenyl - stability 311 thiophosphoric acid 332 Nankor, see Ronnel Methyl Trithion, properties and uses 366 Naphthalene 26, 27 - Trithion, synthesis 366 Naphthoic acids 144 Methylumbelliferone, properties and uses Naphthol 96 403 Naphthoquinones 115 - synthesis 341 Naphthoxyacetic acids 160, 161, 172 Methylvaleric acid anilides 125 Naphthylacetaldehyde 112 Metmercapturon, see Mesurol Naphthylacetamide 155 Metramak, see Tetram Naphthylacetic acid, properties and uses Meturin, properties and uses 235, 236 154 - synthesis 236 - syntheses 154, 155 Mevinphos, persistence 312 Naphthylacetonitrile, synthesis 154 - properties and uses 311, 312 Naphthyl carbamate, see Carbaryl - syntheses 311 Naphthyldimethyl ether 108 Micronizers 441 I-Naphthyl N-methylcarbamate, Mikazin, properties and uses 241, 281 see Carbaryl - synthesis 281 Naphthylphthalamic acid, see Alanap Milbex 281 I-Naphthylthiourea, see Antu Milk 2, 50, 74, 334 Neburon, properties and uses 232 Mineral oils, see Petroleum oils - synthesis 232 Minimum intervals, use of 6 Nemacide, properties and uses 332 Mipafox, properties and uses 316 - synthesis 332 Subject Index 471

Nemacide oxon 332 Octyl thiocyanate 253 Nemacure 40 Omadine preparations 405 Nemagon, properties and uses 35, 38, 39 OMPA, see Sdlradan - synthesis 39 OMU, properties and uses 201, 226, 228, 229 Nematocides, definition 3 - syntheses 229 Nematode control 35, 38-40, 67, 82, 198, Onions 40,125,152,181,200,226,232, 206 If., 213, 223, 332, 337, 340, 396, 314, 384, 437 398,415,430,431 - pest-caused losses 5 Neo-azazin 393 OP-7, properties and uses 17, 18,29, Neopynamin 131 If. 176,260 Nicotine 396, 405, 406 - synthesis 108 Nirite, see DNTB OP-10 17, 108 Nirosan 398 Optical glass, deterioration 2 Nitralin, synthesis 84 Ordram, see Molinate Nitriles, pesticidal properties 128, 142 Organodllorine compounds, breakdown in Nitrobenzenesulfonyl carbamate, petroleum fractions 30 see Compound MB-8882 Organolead compounds, see Lead Nitro compounds, pesticidal properties Organomercury compounds, see Mercury 78 If., 81 If. Organophosphorus compounds, Nitroethylene 78 nomenclature 305 If. Nitrofen 102 - compounds, pesticidal properties 303 If. 5-Nitrofurfural semicarbazone, properties, Organotin compounds, pesticidal properties synthesis, and uses 397 and uses 285, 297 If. 4-Nitro-3-methyl phenol, synthesis 330 - compounds, poisoning 301 p-Nitrophenol, properties and uses - compounds, syntheses 299 If. 97, 324-329, 384 Ortho 5353 191 - synthesis 97 Oryzon 92 Nitrophenols, pesticidal properties 96 If. Ovex, organoleptic elfect 272 4-Nitrophenyl-2' -nitro-4'-trifluoromethyl- permissible concentration in air 272 phenyl ether, see C-6989 - properties and uses 269, 271-273, 275 4-Nitrophen yl-2,4,6-tridllorophenyl ether, - syntheses 272, 273 see MO Granules Ovotran, see Ovex Nitrostyrenes, properties and uses 78 Oxime hydrazones 279 - synthesis 79 Oxine, properties and uses 409, 410 Nonadllor 56, 57 - syntheses 410 Nonyl alcohol 89 4-0xo-3,4-dihydro-1 ,2,3-benzotriazine, Norea, properties and uses 229, 230 synthesis 372 - synthesis 229 Oxydemetonmethyl, properties and uses Nornicotine 405, 406 348, 349 NPD 379 syntheses 349 Nuvan, see Didllorvos tolerance 349

Oats 19, 68, 184, 202, 269 Paints and lacquers, pesticidal 12, 20 Octadllor 56-58 Panogen, properties and uses 290-292 Octadllorocyclohexane 47 - synthesis 291 Octadllorocyclohexenone, see Octone Paper, insecticidal 12, 23 Octadllorodipropyl ether 108 Paraformaldehyde, uses 111 1,3,4,5,6,7,8,8-0ctadlloro-3a,4,7,7 a -tetra­ Paraldehyde, see Paraformaldehyde hydro-4,7 -endomethylenenaphthalene, Paraoxon 324, 325 see Isobenzan Paraquat, properties and uses 36, 407-409 Octadecenediol acetate, see Gyplure - synthesis 407 Octamethyl, see Sdlradan Parathion, analytical method 324 Octamethylpyrophosphoramide, - dusts 14 see Sdlradan explosive properties 324 Octone, properties and uses 49, 112, 113 metabolism 324 If. - synthesis 112 permissible concentration in air 326 472 Subject Index

Parathion, properties and uses 97, 303, 304, Perthane, synthesis 76 323--330, 332, 338, 379, 384 -- tolerance 76 -- synthesis 326 Pest-caused losses in agriculture 1, 5 if. -- tolerances 325 Pesticide-fertilizer combinations 16 Paris green, properties and uses 388, 389 Pesticide use, economic efficiency 5 if. -- green, syntheses 388 Pesticides and enzyme systems 7 Parsley 125 -- and formulations, numbers of 6 Paste formulations 18--20, 22 annual production 6 Patoran 234, 235 -- application methods 9 if. PCBA, see Blastin -- memistry of (see also specific PCB compounds 44 compounds) 1 if. PCPB, see Fenson conversion products (see also specific PCPCBS, see Ovex compounds) 9 Peames 405 definition and types 3 -- pest-caused losses 1 formulations 12 if. Peanuts 232, 353 general requirements for 6 if. Pears 102,173,274,289,418 -- ideal properties 9 -- pest-caused losses 5 -- increased yields from 5 if. Peas 109, 147, 155, 159, 210, 211, 229, 418 in environment, U.S.S.R. 6 Peat carbolineum and tar 32, 33 -- memanisms of action 7 -- dry distillation 32 -- methods of use 9 if. Pencils, insecticidal 12, 20 persistence 8 if. Pentac 55 production in the U.S.s.R. 6 Pentamloroacetone 112 solvents (see also specific compounds) 20 Pentamloroacetophenone 315 stability (see also specific compounds) 9 Pentamloroanisole 106 toxicity of metabolites 7, 9 Pentamlorobenzoic acid 147 volatility (see also specific compounds) Pentamlorobenzyl alcohol, see Blastin 8 Pentamlorocyclohexene 45 Pestox, see Dimefox Pentamloroethane 35 Pestox -III, see Smradan Pentamloroethyl mercaptan, synthesis 249 Pestox-15, see Mipafox Pentamloroisopropylbenzene 67 Pests, types 1 Pentamloromandelonitrile 92 -- world losses from 3 Pentamloronitrobenzene, analytical method Petrolatum 30 82 Petroleum oils, agricultural uses 27 if. -- properties and uses 81, 82, 125,201 oils and frost resistance 29 -- synthesis 82 -- oils, memanism of action 4, 30 Pentamloropentadienoic acid 122 -- oils, oxidation 28, 30 Pentamlorophenol, analytical method 105 -- oils, photooxidation 28, 29 properties and uses 48, 49, 104--107, -- oils, properties and uses 27 if. 115,178 PH 40--21, properties and uses 418, 419 syntheses 106 -- synthesis 418, 419 Pentamlorophenoxyacetic acid 158 Phaltan, see Folpet Pentamlorothiophenol 48, 69 Phenarsazine 390 3-sec-Pentylphenyl N -methylcarbamate, Phenazon, see Chlorazine see Ortho 5353 Phenkapton, properties and uses 364, 366 Peppers 82, 112 -- synthesis 366 Permloro(methyl mercaptan), properties Phenmedipham, see Betanal and uses 240, 245, 246, 248--251, 253, Phenols, pesticidal properties 92 if. 264 Phenothiazine, properties and uses 416, 424 syntheses 246, 247 -- synthesis 424 Permloro(methyl mercaptans), pesticidal Phenoxarsine 390 properties 245 if. Phenoxarsine oxide 394 Persistence of pesticides (see also specific Phenoxyacetic acids 157 if. compounds) 8 if. S-Phenoxyarsinyl O,O-diethyl dithiophos- Perthane, properties and uses 76 phate, see Thiarsine Subject Index 473

Phenoxyethylamine, mode of action 84 Photodecomposition 9, 15 Phenthiuram 50 Photosynthesis 186 Phenylacetic acids 143 Phthalan, see Folpet 1-Phenyl-4-amino-5-chloropyridazone-6, Phthalophos, see Imidan see Chlorazine Phygon, see Dichlone N-Phenyl-N',N'-dimethylurea, see Fenuron Picloram, properties and uses 403, 404 N -Phenyl-N-hydroxy-N' -methylurea, - synthesis 403, 404 see Meturin PIMM 295 Phenylmercuric acetate, see Ceresan Pin done, properties and uses 114 Phenylmercuric bromide 295, 298 - synthesis 114 Phenylmercuric chloride 295 Pineapples 422 N -(Pheny Imercuri)-l ,4,5,6,7,7 -hexachloro­ Pinene, chlorinated 50 bicyclo [2.2.1] heptene-5-dicarboximide Piperazine 416 295 Piperonyl butoxide, properties and uses Phenylmercuripyrocatechin 295 108, 109, 413 Phenylmercuritriethanolammonium lactate, - butoxide, synthesis 109 see Puratized Piperonyl cyclonene, properties and uses Phenylmercuriurea 295 113, 114,413 N -Phenyl-N'-(2-methylcyclohexyl)urea 226 - cyclonene, synthesis 113 I-Phenyl-3-methylpyrazolyl-5 dimethyl- Pirofos, see Sulfotepp carbamate, see Pyrolan Pival, see Pindone Phenyl sulfone, see Diphenyl sulfone Pivalin, see Pin done Phenylthiourea 238 2-Pivalylindandione-1,3, see Pin done Phorate, metabolism 364, 365 Plant sterilants 122 persistence 365 Plantvax, properties and uses 423, 424 - properties and uses 364-366 - synthesis 424 - syntheses 365, 366 PMAC, see Ceresan Phorate sulfoxide and sulfone 364, 365 Polarography 358 Phosalone, metabolism 371 Polycarbacine, see Polyram - properties and uses 371 Polycarbazine 211 - synthesis 371 Polychlorobiphenyls, see PCB compounds Phosbutyl, properties and uses 374, 375 Polychlorocamphene 51 - synthesis 375 Polychlorocyclodienes 52 ff. Phosdrin, see Mevinphos Polychloroethylenes 36 Phosgene 37, 54, 178, 182, 186-189, 193, Polychloronaphthalenes 44 195,198,203,208,229 Polychloropinene, see Chlorothene Phosphamide, see Dimethoate Polychloroterpenes 50 ff. Phosphamidon, metabolism 313 Polyethylenebis(thiuram sulfide and - properties and uses 313, 314 disulfide) 222 - synthesis 314 Polyram, properties and uses 220 Phosphine 305-307, 446 - synthesis 220, 221 Phosphinon, see Phosthenon Potasan, properties and uses 340, 341 Phosphonic acid derivatives, pesticidal - synthesis 340, 341 properties 380 ff. Potassium chlorate 445 - acid derivatives, syntheses 381 Potato famine, Irish 1 Phosphopyrone, see Endothion Potatoes 1, 3, 48, 82, 89, 91, 108, 155, 157, Phosphoric acid derivatives, pesticidal 186, 196, 209, 217, 221, 222, 226, 229, properties 308 ff. 232,235,236,249,252,262,276,301, Phosphorous acid derivatives, pesticidal 302,308,369,373,419,432 properties 307 ff. pest-caused losses 1, 5 Phosphorus compounds, pesticidal Powders 12 ff. properties 44 5 ff. PP-407, properties, synthesis, and uses Phosphorus pentasulfide, synthesis 357 408,409 Posthenon, properties and uses 311 PP-745, properties, synthesis, and uses 409 - synthesis 311 Prefix, properties and uses 145 Phostoxin 446 - synthesis 145 474 Subject Index

Preparation G-4-40 107 Quaternary ammonium bases, properties Prep-Defoliant 122 and uses 86 if. Probanil 200 - ammonium bases, synthesis 86 Prolan 80 Quinces 366 Prometryne, properties and uses 437 Quinoline-8-sulfonic acid, synthesis 410 - syntheses 437 Quinolinol, see Oxine Promurite, properties and uses 237 8-Quinolinol benzoate or sulfate, - synthesis 237 see Quinosol Propachlor 126 Quinomethionate, see Chinomethionate Propanide 124, 125 Quinone oxime benzoylhydrazone, Propargyl bromide 36, 41 see Cerenox Propazine, properties and uses 200, 436, Quinones, pesticidal properties 115 if. 437 Quinosol, properties and uses 411 - synthesis 436 - synthesis 411 Propham and cancer 199 Quinoxaline-2,3-trithiocarbonate, properties and uses 184, 185, 199, 200, see Eradex 202,204 stability 200 synthesis 200 R-1607, see Vernam Propineb 222 Randox and Randox-T 125 S-n-Propyl N,N-di-n-propylthiocarbamate, Ratindan, properties and uses 114, 115 see Vernam - synthesis 114 Propylene oxide 396 S-Propyl N-ethyl-N-butylthiocarbamate, Rats, destructive ability 1 see Tillam Repellent MGK-326 403 Propyl isome 413, 414 Repellents 3, 117, 151, 152,227,237,401, Propyl thiopyrophosphate, see NPD 403,411 Proxypham, analytical method 204 - definition 3 persistence 204 Residue laboratories, U.S.s.R. 6 - properties and uses 204 Residues, safety in use 6 - synthesis 204 Resitox, see Coumaphos Puratized, properties and uses 295, 296 Rhizoctol, see Methylarsine sulfide - synthesis 296 Rhodan, properties and uses 254, 259, 260 Pyramin, see Chlorazirte - synthesis 260 Pyrazon, see Chlorazine Rice 92,109,113,124,137,145,153,190, , air inactivation 132 191,203,206,210,290,302,315,352, - properties and uses 25, 63, 113, 130 if., 375, 392, 393, 418 256, 397, 413 Rodent control 10, 12,51, 108, 114, 115, , synthesis and uses 108, 132 if. 119,237,238,263,265,388,400-403, Pyridine-thiol-2 oxide-I, properties, 416,422,445,446 synthesis, and uses 405 Rodenticides, definition 3 Pyridinitrile, properties and uses 405 Rogor, see Dimethoate - synthesis 405 Romate, properties and uses 196 Pyridylmercuric acetate and chloride 284 - synthesis 196 Pyrolan, properties and uses 188, 197 Ronnel, properties and uses 320, 332-335, - synthesis 197 337 Pyrophosphoric acid derivatives, - syntheses 333, 334 pesticidal properties 376 if. Root induction 398 - acid derivatives, syntheses 377 if. Roses 102,264,278,289,427,443 Rotenone 414 Quaternary ammoaium bases, analytical Round worms, see Nematode control method 86 Rubber protection 97, 103 ammonium bases as bactericides 85, 86 Ruelene, persistence 317 ammonium bases, mode of action 87 - properties and uses 317, 318 ammonium bases, pesticidal properties Rutgers-612 90,401 83 if. Rye 438 Subject Index 475

Salicylanilide, properties and uses 142, 148 Sodium p-dimethylaminobenzenediazo­ - synthesis 148 sulfonate, see Dexon Salicylic acid esters 141 Sodium ethylxanthate, synthesis and uses - acid in canning 148 179,180 Sodium fluosilicate 444 Salithion 336 Sodium isopropylxanthate, properties and Sa yfos, see Menazon uses 179, 180 , metabolism 379, 380 - isopropylxanthate, synthesis 180 permissible concentration in air 379 properties and uses 304, 376, 378-380 Sodium N -methyldithiocarbamate, stability 379 see Carbothion synthesis 380 Sodium tetrathionate 264 SD91-29 314 Soil sterilization 78, 181,206,213,230, Seed disinfectants 4, 19, 50, 59, 63, 69, 78, 260, 262, 385, 428 81,82,87,95,96,104,105,111, Solan 125 115-117,149,216,247,254,260,279, Solbar 188, 442 281-285,287-296, 301 if., 371, 387, Solid solutions of pesticides 20 388,391,394,411,415,418,423,443, Solutions as formulations 12, 19 if. 446 Solvents, intermediate 24 Seedvax, properties and uses 419 for formulations 20 - synthesis 419 - for pesticides (see also specific compounds) 20 Semesan preparations 293 Sere don, see Cerenox Soy beans 3, 125, 148, 155, 203, 229, 234, Seredon Special 282 235 413 Spinach 76 Sesamin 413, 414 Sprouting inhibitors 5, 48, 82, 89, 108, 155, Sesin 108 186 Sesoxane, see Sesamex Stability of pesticides (see also specific Sevin, see Carbaryl compounds) 9 Sex sterilants 3, 122, 318, 369, 415, 439 Starn F-34, see Propanide Sheep 387 Stannic and stannous chlorides 298 - chemical shearing 446, 447 Stauifer R-4572, see Molinate Siglure 139 Stem thickeners 282 Sterilants, see under plant, sex, soil Silica gel Aerogels 4, 446 Stomach insecticides, definition 3 Silk 1 Silvex, properties and uses 173 Storage stability 9 - synthesis 173 Stored-product protection (see also specific Simazine, persistence 435 products) 25, 35, 37, 38, 40, 65, 122, - properties and uses 435, 436, 438 123, 128, 136, 176,240,445,446 - synthesis 435 Strawberries 125, 155, 216, 264, 308 Simetone 435 - increased yield from pesticides 5 Simetryne 435 Strobane, properties and uses 50, 52 Sinerfos 347 - synthesis 52 Slime control 112, 285, 287, 288, 296 if., Sugarbeets 52, 59, 116, 120, 125, 126, 157, 301 184,200,201,203,206,210,226,228, Smoke pots 23 229,236,279-282,301,302,317,366, Smokes, insecticidal 23 419, 420, 422, 423 Snail control 111, 149,424 Sugarcane 120, 276 Soaps, insecticidal 12, 22 Sulfides, pesticidal properties 240 if. Sodium arsenate, synthesis 389 Sulfites, acaricidal properties 265, 266 Sodium arsenite, properties and uses 387 Sulfones, acaricidal properties 242, 243 - arsenite, synthesis 387 Sulfonic acid derivatives, pesticidal Sodium bisulfite 265 properties 269 if. Sodium borate 445 - acid amides, pesticidal properties 274 if. Sodium chlorate, explosive hazard 445 Sulfonyl fluorides 276 Sodium chloride, pesticidal properties 443 Sulfotepp 23, 379 476 Subject Index

Sulfur and compounds, pesticidal properties Tetrachlorobenzenes 48, 49, 68, 102, 103, 6,264,265,333,357,424,441 if. 244 Sulfur dioxide 37, 265, 441 Tetrachlorobenzoic acids 147 Sulfuric acid derivatives, pesticidal Tetrachlorobenzoquinone, see Chloranil properties 262 if. Tetrachlorocyclohexadiene 45 Sulfurous acid derivatives, pesticidal Tetrachlorocyclohexene 46 properties 262 if., 265 if. 2,4,5,4'-Tetrachlorodiphenyl sulfone, Sulfuryl fluoride, properties and uses 263 see - fluoride, synthesis 263 Tetrachloroethanes 35 Sulphenone, properties and uses 243, 245 Tetrachloroethylene 55 - synthesis 245 N -1,1,2,2-Tetrachloroethylthiotetrahydro- Sumithion, see Fenitrothion phthalimide, see Difolatan Summer oils 27, 29 Tetrachloronitrobenzene 48, 81, 82 Sunflowers 157, 438 Tetrachlorophenols 105, 106 Surcopur, see Propanide Tetrachlorophenoxyacetic acids 158 if. Swep, properties and uses 203, 204 Tetrachloropyridine 340 - synthesis 204 Tetradecyl thiocyanate 253 Synergism 132, 136, 347, 413 if. Tetradichlone, see Tetradifon Systam, see Schradan Tetradifon, properties and uses 243, 244 Systemic herbicides, definition 4, 5 - synthesis 244 - insecticides, definition 3 Tetraethyl dithiopyrophosphate, Systox, see Demeton see Sulfotepp 0,0,0,0-Tetraethyl S,S' -methylenebis(di- thiophosphate), see Ethion 2,4,5-T, properties and uses 48, 49, 103, Tetraethyl monothiopyrophosphate 379 120, 158, 161, 171-173 Tetraethyl pyrophosphate, see TEPP - synthesis 171 Tetraethylthiuram disulfide 216 2,4,5-T esters, properties and uses 171,172 Tetraethyltin 298 2,4,5-T salts, properties 171 Tetraethyltrithiopyrophosphate 373 Tabatrex, see Dibutyl succinate N -(Tetrahydrodicyclopentadienyl)-N' ,N' - Tag, see Ceresan dimethylurea, see Norea Taiga 152 Tetrahydrophthalimide, synthesis 248 Tanalite 389 Tetrahydroquinoline, synthesis 412 2,4,5-TB, properties and uses 175 Tetrahydrothiazine 428 - synthesis 175 3-(0<-Tetralyl)-4-hydroxycoumarin, TDE and cancer 76 see Coumatetralyl - properties and uses 76 Tetram, isomers 352 - synthesis 76 - properties and uses 352, 353 Tedion, see Tetradifon - synthesis 352, 353 Telodrin, see Isobenzan T etramethylenedisulfotetramine, Telone 39 see Tetramine Temik, see Aldicarb Tetramethylphosphorodiamidic fluoride, Tenoran, properties and uses 226, 232 see Dimefox - synthesis 232 Tetramethyl pyrophosphate 376 Tepa 318 0,0,0',0'-Tetramethyl 0,0'-thiodi-p- TEPP, properties and uses 304, 376-379 phenylene phosphorothioate, see Abate - smoke pots 23 Tetramethylthiuram disulfide, see TMTD - stability 378 Tetramethylthiuram monosulfide 216 Terbacil 421, 422 Tetramine, properties and uses 263 Terpenes, chlorination products (see also - synthesis 263 specific terpenes) 50 if. 1,3,6,8-Tetranitrocarbazole, see Nirosan Terracur-p, see Fensulfothion Tetra-n-propyl dithiopyrophosphate, Terra-Systam, see Dimefox see NPD Tetrabromocyclohexane 44 Tetrathion, properties and uses 369 Tetrabromodichlorocyclohexanes 44 - synthesis 369 Tetrachloroacetophenone 314, 315 Tetrazole 428 Subject Index 477

TH 052 H, see PH 40-21 Thiophos-ME, see Methylethylparathion Thallium sulfate 446, 447 Thiophosphates, syntheses 321 if. Thanite, mode of action 255 Thiophosphoric acid derivatives, pesticidal - properties and uses 254, 257, 258 properties 319 if. - synthesis 257, 258 Thiosulfonic acid esters 277 Thiadiazinethione, analytical method 431 Thiotepa 318 - properties and uses 430-432 Thiourea and derivatives, pesticidal - synthesis 432 properties 213, 225 if., 236 if., 260, 327, Thiarsine, properties and uses 394 437 - synthesis 394 Thiram, see TMTD 2-(Thiazolyl)benzimidazole 418 Thiuram-D, see TMTD Thiazone, properties and uses 430, 431 Thiuram disulfide, see TMTD - stability 430 Tillam 209, 210 - synthesis 431 Tinox, isomerization 348 Thimet, see Phorate - properties and uses 347, 348 Thinol424 TMTD, explosive properties 215 Thiocarbamic acid esters, pesticidal - properties and uses 50, 104, 211, properties 207 if. 215-217, 392 - acid esters, synthesis 207 if. - synthesis 215 Thiocarbamic acids, pesticidal properties TO-2, see CMPT 206 if. Tobacco 89, 196,406,432 Thiocarbonic acids, pesticidal properties - alkaloids 405, 406 177 if. - arsenic in 387 - acids, synthesis 178 if. TOK E-25, properties and uses 109 Thiocron, see Amidithion - E-25, synthesis 109 Thiocyanates, mode of action 255 Tomato ripening 26 - pesticidal properties 252 if. Tomatoes 19, 82, 112, 142, 148, 155, 161, Thiocyanoacetic acid 253 172 Thiocyanoacetone 254 - increased yields from pesticides 5 4-Thiocyanoaniline, see Rhodan Tooth damage by cryolite 444 Thiocyanobutyric acid 253 Tordon, see Picloram p-Thiocyanoethyl laurate, see Lethane 60 , analysis 51 4-Thiocyanophenyl methanesulfonamide as rodenticide 51 275 - composition 51 Thiocyanopropionic acid 253 IR absorption 51 y-Thiocyanopropyl-2,4,6-trimethylphenyI properties and uses 51 if., 58 ether 254 synthesis 51 Thiodan, see Endosulfan tolerances 51 Thiodiphenylamine, see Phenothiazine Toxicity, acute vs. mronic 7 Thiolo and thiono isomers 319 if. dermal 7 Thiolocarbamic acids, pesticidal properties evaluation in E. and W. Germany 7 206 if. evaluation in U.S.S.R. 7 if. Thiolomlorocarbonates, synthesis 208 inhalation 7 Thiometon, metabolism 367 selective 8 permissible concentration in air 368 2,4,5-TP, see Silvex properties and uses 367-369 Trialkyltin acetates 298 stability 367 Triallate, properties and uses 211 syntheses 368 - synthesis 211 Thio-mevinphos 312 Triamylamine 83 Thionazin, properties and uses 321, 340 s-Triazines, properties 432 if. - synthesis 340 - syntheses 434 if. Thioneb, synthesis and uses 222 - tautomerism 433 Thionocarbonates, synthesis 179 1,2,4-T riazol yl-3-urea 430 Thiophone 396 Tribenzylamine 83 Thiophos, see Parathion Tribonate 100 Thiophosgene 179, 182,245, 247 Tribromophenoxyacetic acids 158 478 Subject Index

Tributyltin acetate, properties and uses Trichloromethyl thiocyanate, properties and 299,301 uses 253 - acetate, synthesis 301 Trichloromethylthioethers, synthesis 251 Tributyltin chloride 297, 301 N -Trichloromethylthiophthalimide, Tributyltin fluoride 297 see Folpet Tributyltin hydroxide, properties and uses 'Trichloromethylthiosulfonates 250 301 N -Trichloromethylthiotetrahydrophthal­ - hydroxide, stability 301 imide, see Captan - hydroxide, synthesis 301 Trichloronate 385 5,5,5-Tributyl trithiophosphate, see Butifos 2,4,5-Trichlorophenol, analytical method Tributyl trithiophosphite, see Merphos 104 Trichlorfon, methylating ability 382 dissociation constant 309 permissible concentration in air 382 properties and uses 48, 49, 102 ff., 106, properties and uses 310, 381-383 332-334 stability 382 synthesis 102 syntheses 382, 383 Trichlorophenols 103, 166, 334 Trichlormetafos-3, properties and uses 2,3,4-Trichlorophenoxyacetic acid 172 334, 335, 337 2,4,6-Trichlorophenoxyacetic acid 164 - synthesis 334 Trichlorophenoxyacetic acids 157 ff. Trichloroacetic acid, properties and uses Trichlorophenoxybutyric acid, see 2,4,5-TB 120, 121, 228, 231 2,4,5-Trichlorophenoxyethyl ester of - acid, syntheses 121 dichloropropionic acid, see Erbon Trichlorophenoxypropionic acid, see Silvex Trichloroacetonitrile, properties and uses 2,3,6-Trichlorophenylacetic acid, see Fenac 128 0-2,4,5-Trichlorophenyl dichlorophosphite, - stabilization 128 synthesis 333, 334 5-2,3,3-Trichloroallyl N,N -diisopropylthio­ 0-2,4,5-Trichlorophenyl dichlorothiophos­ carbamate, see Triallate phate, synthesis 333 3,5,6-Trichloro-4-aminopicolinic acid, O-(Trichlorophenyl) diethylthiophosphinate, see Picloram see Agvitor Trichloroanisole 102, 103 Trichlorophenyl ethanol 315 1,2,4-Trichlorobenzene 335 Tri(p-chlorophenyl)tin acetate 298 Trichlorobenzenes 45, 46, 48, 49, 67, 68, Trichloropropanes 39 244 Trichloropropenes 35 2,4,5-Trichlorobenzenesulfonyl chloride, Trichloropropionic acid, properties and uses synthesis 244 122 2,3,6-Trichlorobenzoic acid 145-147 - acid, synthesis 122 Trichlorobenzoic acids 146, 147, 176 Trichloropropionitrile 128 2,3,6-Trichlorobenzoic acid, synthesis 146 Trichlorothiophenol 48 4,5,7 -Trichloro-2, 1 ,3-benzothiadiazole, 2,3,6-Trichlorotoluene, synthesis and uses see PH 40-21 146, 153 Trichlorobenzyl chloride, see Randox-T Trichlorphon 351 Trichlorocampene 50 Tricyclohexyltin acetate 297, 298 Trichlorodibromopropane 35 N -Tridecyl-2,6-dimethylmorpholine, Trichlorodinaphthylethane 75 see E-236 Trichlorodinitrobenzene, see Brassisan Tridipam 213 Trichlorodithienylethane 75 Trietazine 437 Trichloroethanes, toxicity 35 Triethyltin chloride and other salts 2,3,5-Trichloro-4-hydroxypyridine, 298,299 see Daxtron Trifluoromethylaniline, synthesis 233 3,5,6-Trichloro-2-hydroxypyridine, N -(3-Trifluoromethylphenyl)-N' ,N'­ synthesis 339, 340 dimethylurea, see Fluometuron Trichlorometaphos, see Ronnel Trifluorophenoxyacetic acids as herbicides Trichloromethyl chloroalkyl sulfides 246 158 N -Trichloromethylthio-4-chloroanilide of Trifluralin, properties and uses 83, 84 methanesulfonic acid, see Mesulfan - synthesis 84 Subject Index 479

Trilon B 175 Volatility vs. vaporizability 8 Trimedlure 140 Volman's salt 389 Trimethylphenyl N-methylcarbamate 184 Voronit, see Furidazol Trimethyl thiophosphate, synthesis 348 Trimeturon 233 Triphenylamine 83 Warble fly, losses from in U.S.s.R. 2 W ARF antiresistant 275 Triphenyltin acetate, see Brestan Triphenyltin hydroxide 299, 302 Warfarin 401, 402 Triphenyltin oxide 299 Waxes, insecticidal 12, 20 Weed control 27, 68, 83, 84, 89, 91 fr., Tris(l-aziridinyl) phosphine oxide 318 96 fr., 105, 108-110, 112, 113, 119 fr., Tris(l-aziridinyl) phosphine sulfide 318 124 fr., 142 fr., 152 fr., 157 fr., 172 fr., Trisben-200 146 Tris(2,4-dichlorophenoxyethyl) phosphite, 178 fr., 183 fr., 198 fr., 206 fr., 223, 225 fr., 252, 262, 266, 269, 275, 276, see Falone 283, 293, 299, 307, 308, 353, 354, 375, Tris( dimethyldithiocarbamoyl) arsine, 380, 387, 390 fr., 396, 400, 403, 404, see Azomat 407 fr., 416, 418 fr., 426 fr., 430 fr., 445, Tris( ethylene imino )-s-triazines 439 Tris(methylethyleneimino)-s-triazines 439 447 Weeds, consumption of nutrients per Trithion, see Carbophenothion hectare 2, 3 Tritox, see Trichloroacetonitrile - losses from 2, 3 N-Tritylmorpholine, see Frescon - water requirements 2 Trolene, see Ronnel Tumacide, see MTMC Wepsin 427 Wettable powders 12, 16 fr. Turnips 281 - powders, composition 18 Turpentine 28, 30, 50 Wetting agents and herbicidal action 175 fr. Tuzet, see Urbazid Wheat 127, 155, 175, 184,202, 210, 211, 438 UC-8305, properties and uses 336 disinfection 19 UC-10854, properties and uses 193 increased yields from - synthesis 193 1, 5 U ndecachlorocyclohexane 46 Wine 247 Undecylenic acid as herbicide 118 Winter oils 28 Unsulfonatable residue 29 WL 9385 and WL 19805 439 Urab 231 Wofatox, see Methyl parathion U rbasulf, see Methylarsine sulfide Wood preservation 30, 32, 288, 301, 388, Urbazid, properties and uses 392, 393 389, 443, 444 - synthesis 392, 393 Wool preservation 1, 2, 238, 269-271, Urea derivatives, pesticidal properties 275, 295, 301 225 fr. Ureas, mechanism of action 225 fr., 236 Uspulun 293 3,5-Xylenyl N-methylcarbamate, see Maqbarl Varni doth ion, metabolism 350 oxidation products 350 - properties and uses 349, 350 Yalan, see Molinate - synthesis 350 Yellow oils 98 Vancide-F 215 Yield increases from pesticide use 5 fr. Vancide-M 215 Vapam, see Carbothion V-C 13 Nemacide, see Nemacide Zectran, metabolism 195 Vegadex, see CDEC - properties and uses 188, 195, 196 Vernam 209 - synthesis 195 Vitavax, properties and uses 423 Zerlate, see Ziram - synthesis 423 Zinc 2-aminoethylenedithiocarbamate 220 Volatility of pesticides (see also specific Zinc arsenate 388, 389 compound) 8 Zinc arsenite 388 480 Subject Index

Zinc dimlorosalicylanilide 149 Zineb, properties and uses 211, 212, 217, Zinc dimethyldithiocarbamate, see Ziram 219-222 Zinc ethylenebis( dithiocarbamate), - synthesis 219, 220 see Zineb Zinophos, see Thionazin Zinc phosphide 445, 446 Ziram, properties and uses 18, 211, 213, Zinc 1,2-propylenebis( dithiocarbamate), 214, 216, 393 see Propineb - stability 214 Zinc salicylanilide 148 - synthesis 214 Zinc trimlorophenolate, synthesis and uses Zoocides, definition 3 103, 104 ZPS, see Dibutyl adipate Zineb, decomposition 219 Zytron, properties and uses 321, 353 - persistence 219 - synthesis 353