Pesticide chemistry, 32.

Preface 7 Introduction 15 Anti-insect agents (Cy . Matolcsy) 21 Insecticides of natural origin ....................................... 21 Nicotine. anabasine and related derivatives ........................... 21 Pyrethrins and synthetic pyrethroids ................................. 24 Rotenone and rotenoids ........................................... 33 Unsaturated isobutylamides ........................................ 35 Quassia ......................................................... 36 Ryana .......................................................... 36 Sabadilla ........................................................ 37 Toxins of Bacillus thuringiensis ..................................... 37 Insecticidal compounds produced by fungi . . . . . . . . . . . . . . . . . . . . . . . 39 Insecticidal terpenoids .......................... . . . . . . . . . . . . . . . 41 References .................................... . . . . . . . . . . . . . . . 42 Arsenic compounds ............................................... 46 References ....................................................... 47 Chlorinated hydrocarbons ......................................... 47 DDT and its related derivatives .................................... 47 Hexachlorocyclohexane . . . . . . . . . . . . . . . . . . .................... 61 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Chlorinated terpenes .............................................. 66 Cyclodiene derivatives . . . . ..................... 68 Cyclobutapentalene deri ..................................... 82 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85 Carbamates ...................................................... 90 References ....................................................... 106 Organophosphorus compounds ..................................... 108 Phosphoric acid derivatives ........................................ 117 Phosphorofluoridates .............................................. 121 Substituted dialkyl-phenyl phosphates and phosphorothioates . . . . . . . . . . 122 Dialkyl-heteroaryl phosphorothioates ............................... I29 Phosphorothioates and phosphorodithioates containing alkylthioalkyl or arylthioalkyl groups ............................................... 133 Dialkyl-dialkylaminoethyl phosphorothioates . ..................... 138 Dialkyl-vinyl phosphates .......................................... I39 Heteroarylmethyl phosphorothiolates and phosphorodithioates . . . . . . . . . . 143 Phosphorodithioates containing carboxylic acid e and amide groups . . 145 Cyclic phosphates and phosphorothioates . . . . . . . . . . . . . . . . . . . . . . . . . 149 Phosphorylated hydroxylamine derivatives ........................... 150 Esteramides of phosphoric and phosphorothioic acid . . . . . . . . . . . . . . . . . . 151 1 . 1 . 1 1.1.1 1.1.2 1.1.3 1.1.4 1.1.5 1.1.6 1.1.7 1.1.8 1.1.9 1.1.10 1.2 I . 3 1.3.1 1.3.2 I . 3.3 1.3.4 1.3.5 I . 4 1.5 1.5.1 1.5.2 1.5.3 1.5.4 1.5.5. 1 S.6 1.5.7 1 S.8 1.5.9 1.5.10 1.5.11 1.5.12 10 CONTENTS 1.5.13 t1 . 6 1.7 1.8 1.8. I 1.8.2 1.8.3 1.8.4 I . 9 1.9.1 1.9.2 1.9.3 1.10 1.11 2 . 2.1 2.2 2.3 2.4 2.5 2.6 2.1 2.8 2.9 2.10 Phosphonic acid derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References ....................................................... Various insecticides ................................................ References ....................................................... Insecticide synergists .............................................. References ....................................................... Insect growth regulators ........................................... Juvenile hormones and juvenile hormone mimics ...................... Anti-juvenile hormones ............................................ Ecdysones. ecdysoids and anti-ecdysones ............................. Inhibitors of chitin synthesis ....................................... References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Chemosterilants .................................................. Alkylating agents ................................................. Antimetabolites .................................................. Miscellaneous compounds ......................................... References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Pheromones ..................................................... References ....................................................... Antifeedants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . References ....................................................... Acaricides (Cy . Matolcsy) .......................................... Diary1 carbinols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Aromatic nitro compounds ........................................ Derivatives containing a C = N or N = N double bond ................. Heterocyclic compounds ........................................... Organophosphorus compounds ..................................... Organometallic compounds ........................................ Cyclopropane derivatives .......................................... Antibiotics ....................................................... References ....................................................... Chlorinated hydrocarbons ......................................... Compounds containing sulfur ...................................... 3 . Nematocides (Cy . Matolcsy) ........................................ References ....................................................... 4 . Rodenticides (M . Nidasy) .......................................... References ....................................................... 5 . 5.1 Inorganic fungicides .............................................. 5.1.1 Metal salts ...................................................... 5.1.2 Sulfur and its inorganic compounds ................................. References ....................................................... 5.2 Elementorganic compounds ........................................ 5.2.1 Mercury compounds with fungicidal properties ....................... Fungicides (M . Nhdtsy) ............................................ 152 156 161 164 165 171 172 172 193 196 204 208 213 215 219 220 224 225 234 235 239 240 240 241 243 244 246 249 250 251 251 252 254 256 260 261 270 272 272 272 277 281 283 283 CONTENTS 11 5.2.2 5.2.3 5.2.4 5.2.5 5.3 5.3.1 5.3.2 5.3.3 5.3.4 5.4. 5.5 5.5.1 5.5.2 5.5.3 5.5.4 5.5.5 5.6 5.6.1 5.6.2 5.7 5.7.1 5.7.2 5.7.3 5.7.4 5.8 5.9 5.9.1 5.9.2 5.9.3 5.9.4 5.9.5 5.10 5.10.1 5.10.2 5.10.3 5.10.4 5.1 1 Organic tin compounds ............................................ Fungitoxic arsenic compounds ..................................... Organic phosphorus compounds .................................... References ....................................................... Benzene derivatives ............................................... Polychlorobenzenes. chloronitrobenzenes ............................. Phenol derivatives ................................................ Dinitroalkyl phenols .............................................. Quinones ........................................................ References ....................................................... Compounds with fungicidal properties containing a polyhalogen alkanoic sulfenyl group .................................................... References ....................................................... Dithiocarbonic acid derivatives ..................................... N-Monoalkyldithiocarbamates ..................................... N.N.Ethylen e-bisdithiocarbamates .................................. Dialkyldithiocarbamates ........................................... Mode of action and mechanism .................................... Aspects of environmental protection ................................ References ....................................................... Carboxamides and carboximides .................................... Carboxamides .................................................... Dicarboximide derivatives ......................................... References ....................................................... h o l e compounds ................................................ Imidazole and its derivatives ....................................... Benzimidazole derivatives and precursors ............................ Triazoles ........................................................ Oxazoles and thiazoles ............................................ References ....................................................... Fungicides of formamide type ...................................... References ....................................................... Various heterocyclic fungicides ..................................... Pyridine derivatives ............................................... Pyrimidine derivatives ............................................. Quinoline derivatives .............................................. Quinoxaline derivatives ............................................ Morpholine-type fungicides ........................................ References ....................................................... Other compounds with fungicidal properties .......................... Alkane derivatives ................................................ Alkane carboxylic acid derivatives .................................. Aromatic compounds ............................................. Biodegradable pesticides ........................................... References ....................................................... Agricultural antibiotics ............................................ References ....................................................... Organic boron compounds ......................................... 296 300 302 309 309 313 313 319 321 326 329 332 342 343 346 349 352 354 361 366 369 369 378 382 385 385 388 403 411 415 421 426 427 427 430 437 441 442 445 448 448 451 456 463 464 468 483 12 CONTENTS 6 . 6.1 6.1.1 6.1.2 6.1.3 6.1.4 6.1.5 6.1.6 6.2 6.3 6.4 6.4.1 6.4.2 6.4.3 6.4.4 6.4.5 6.4.6 6.4.1 6.5 6.5.1 6.5.2 6.5.3 6.5.4 6.6 6.7 6.8 6.9 6.10 6.10.1 6.10.2 6.10.3 6.10.4 6.10.5 6.10.6 6.1 I 6.12 Herbicides (V . Andriska) ........................................... Inorganic herbicides .............................................. Sulfuric acid and its derivatives ..................................... Cyanates. thiocyanates and cyanamides .............................. Chlorides and chlorates ........................................... Boron compounds ................................................ Arsenic compounds ............................................... Azides .......................................................... References ....................................................... Halogenated-alkanoic acid derivatives ............................... References ....................................................... Benzoic acids .................................................... References ....................................................... Phenoxyalkanoic acids and their derivatives . (Phenoxy herbicides) ....... Phenoxyacetic acids ............................................... Phenoxypropionicacids ........................................... Phenoxybutyricacids .............................................. Structure-activity relationships ..................................... Mode of action and biodegradation of phenoxy herbicides ............. Phenoxyethanol herbicides ......................................... Phenoxy-phenoxy acids ............................................ References ....................................................... Amides ......................................................... N-Substituted a-chloroacetamides ................................... N-Substituted amides of other acids ................................. N-Chloroacetyl-N-phenylglycinee sters .............................. OthCramides .................................................... References ....................................................... Phenols ......................................................... References ....................................................... Nitrodiphenyl ethers .............................................. References ....................................................... Nitriles .......................................................... References ........................................................ Dini troanilines ................................................... References ....................................................... Carbamates ...................................................... N-Alkylcarbamic acid esters ....................................... N-Arylcarbamic acid esters ........................................ Oxime carbarnates ................................................ Sulfonyl carbamates .............................................. Carbamic acid esters with two carbamate groups or with an urea group .. Physiological and biochemical action of carbamates . . . . . . . . . . . . . . . . . . . References ....................................................... Thiocarbamates .................................................. References ....................................................... Di thiocarbamates ................................................. References ....................................................... 487 487 488 489 490 491 492 492 494 495 498 499 502 503 504 508 510 515 521 531 541 546 550 551 562 564 566 514 577 580 581 584 585 590 591 611 614 614 619 626 628 629 634 634 636 649 650 652 CONTENTS 6.1 3 Urea herbicides .................................................. 652 6.13.1 Aliphatic urea derivatives .......................................... 653 6.13.2 Cycloaliphatic urea derivatives ..................................... 654 6.13.3 Aryl urea derivatives .............................................. 656 6.13.4 Arylalkoxy urea derivatives ........................................ 665 6.1 3.5 Other 3-aryl-1-substituted urea derivatives ........................... 669 6.13.6 3-Aryl-3-hydroxy-I -alkyl urea derivatives 672 6.13.7 3-Acyl-3-aryl- I , I -dialkyl urea derivatives ............................. 673 6.13.8 Urea derivatives containing a heterocyclic group ...................... 674 6.13.9 Thiourea derivatives .............................................. 678 6.13.10 Action and mode of action of urea herbicides ........................ 678 References ....................................................... 691 6.14 s-Triazine derivatives .............................................. 694 6.14. I 2-Chloro-4, 6-alkylated diamino-s-triazines ............................ 701 6.14.2 2-Chloro-4-alkylamino-6-cyanoalkylamino-~-triazines . . . . . . . . . . . . . . . . . 704 6.14.3 4,6-Bis(alkylamino)-2-alkoxys-- triazines .............................. 708 6.14.4 4,6-Bis(alkylamino)-2-alkylthiso--t riazines ............................ 709 6.14.5 s-Triazines containing an azido group ............................... 710 6.14.6 Action of s-triazine herbicides ...................................... 711 References ....................................................... 724 6.15 1.2.4-Triazinones ................................................. 727 Rererences ....................................................... 730 6.16 Pyridines ........................................................ 731 References ....................................................... 737 References ....................................................... 743 6.18 Uracils .......................................................... 743 References ....................................................... 746 6.19 Quaternary ammonium salts ....................................... 747 References ....................................................... 756 6.20 Azoles .......................................................... 757 References ....................................................... 764 6.2 I Organophosphorus compounds ..................................... 765 References ....................................................... 771 6.22 Organoarsenic compounds ......................................... 772 References ....................................................... 774 6.23 Sulfonylurea herbicides ............................................ 774 References ....................................................... 777 6.24 Other herbicides .................................................. 778 References ....................................................... 785 ............................ 6.17 Pyridazines ...................................................... 738 Subprtindex ..................................................... 787