(12)
`
`UK Patent Application WGB (11) 2 457 347 as) A
`
`(21)
`
`Application No:
`
`0822837.1
`
`(51)
`
`(43) Date of A Publication
`
`19.08.2009
`
`INT CL:
`A01N 43/56 (2006.01)
`A01P 7/04 (2006.01)
`
`A01P 3/00 (2006.01 )
`
`(56) Documents Cited:
`None
`
`(58) Field of Search:
`Other: No search performed: Section 17(5)(b)
`
`Date of Filing:
`
`Priority Data:
`(31) 0800761
`
`15.12.2008
`
`(32) 16.01.2008
`
`(33) GB
`
`Applicant(s):
`Syngenta Participations AG
`(Incorporated in Switzerland)
`Schwarzwaldallee 215, CH-4058 Basel,
`Switzerland
`
`|nventor(s):
`Harald Walter
`Daniel Stierli
`Ulrich Johannes Haas
`
`Agent and/or Address for Service:
`Syngenta Limited
`PO Box 3538,
`Intellectual Property Department,
`Jealotts Hill Research Centre,
`BRACKNELL, Berks, RG42 6YA,
`United Kingdom
`
`
`
`(22)
`
`(30)
`
`(71)
`
`(72)
`
`(74)
`
`(54)
`
`(57)
`
`Abstract Title: Fungicidal compositions
`
`A method of controlling phytopathogenic diseases on useful plants or on propagation material thereof, which
`comprises applying to the useful plants, the locus thereof or propagation material thereof a combination of
`components A) and B) in a synergistically effective amount, wherein component A) is a compound of formula I
`
`‘l
`
`O
`
`R
`
`F?
`
`CH3
`
`\
`
`22
`
`Y
`
`.
`
`|
`( )
`
`\
`
`IN
`N\
`CH
`
`3
`
`wherein
`R is CF2H or Cr3;
`Z1 is halogen;
`Z2 is halogen; and
`Y is hydrogen or halogen; and agronomically acceptable
`salts/isomers/enantiomers/tautomers/N-oxides of those compounds; and component B) is a compound selected
`from compounds known for their fungicidal and/or insecticidal activity, is particularly effective in controlling or
`preventing fungal diseases of useful plants.
`
`Original Printed on Recycled Paper
`
`V1’7819’?38E)
`
`

`

`2457347
`
`FUNGICIDAL COMPOSITIONS
`
`The present invention relates to novel fungicidal compositions for the treatment of phyto-
`
`pathogenic diseases of useful plants, especially phytopathogenic fungi, and to a method of
`
`controlling phytopathogenic diseases on useful plants.
`
`It is known from WO 2007/141009 and WO 2007/060164 that certain N-[2-(phenyl)ethyl]-
`
`carboxamide derivatives have biological activity against phytopathogenic fungi. On the other
`'hand various fungicidal compounds of different chemical classes are widely known as plant
`
`fungicides for application in various crops of cultivated plants. However, crop tolerance and
`
`activity against phytopathogenic plant fungi do not always satisfy the needs of agricultural
`
`practice in many incidents and aspects.
`
`There is therefore proposed in accordance with the present invention a method of controlling
`
`phytopathogenic diseases on useful plants or on propagation material thereof, which
`
`comprises applying to the useful plants, the locus thereof or propagation material thereof a
`
`combination of components A) and B) in a synergistically effective amount, wherein
`
`component A) is a compound of formula l
`
`10
`
`15
`
`21
`
`o
`
`R
`
`H
`CH
`
`3
`
`,
`
`l
`
`0
`
`\
`
`\ MIN
`\CHa
`
`22
`
`Y
`
`20
`
`wherein
`
`R is CFZH or CF3;
`
`Z1 is halogen;
`
`22 is halogen; and
`
`Y is hydrogen or halogen;
`
`25
`
`and agronomically acceptable salts/isomers/enantiomers/tautomers/N-oxides of those
`
`compounds; and component B) is.a compound selected from the group consisting of
`
`a strobilurin fungicide, such as azoxystrobin (47). dimoxystrobin (226), fluoxastrobin (382),
`
`kresoxim-methyl (485), metominostrobin (551), orysastrobin, picoxystrobin (647),
`
`pyraclostrobin (690); trifloxystrobin (832); the comp0und of formula B-6
`
`

`

`0 \
`
`(Ia-6);
`
`an azole fungicide, such as azaconazole (40), bromuconazole (96), cyproconazole (207),
`
`difenoconazole (247), diniconazole (267), diniconazoIe-M (267), epoxiconazole (298),
`
`fenbuconazole (329), fluquinconazole (385). flusilazole (393), fiutriafol (397), hexaconazole
`
`(435), imazalil (449), imibenconazole (457), ipconazole (468), metconazole (525),
`
`myclobutanil (564), oxpoconazole (607), pefurazoate (618), penconazole (619), prochloraz
`
`(659), propiconazole (675), prothioconazole (685), simeconazole (731), tebuconazole (761),
`
`tetraconazole (778), triadimefon (814), triadimenol (815), triflumizole (834) triticonazole
`
`(842), diclobutrazol (1068), etaconazole (1 129), furconazole (1 198), furconazole-cis (1 1 99)
`
`and Quinconazole (1378); and
`
`a phenyl pyrrole fungicide, such as fenpiclonil (341) and fludioxonil (368); and
`
`an anilino-pyrimidine fungicide, such as cyprodinii (208), mepanipyrim (508) and pyrimethanil
`
`(705);
`
`a morpholine fungicide, such as aldimorph, dodemorph (288), fenpropimorph (344),
`
`tridemorph (830), fenpropidin (343), spiroxamine (740); piperalin (648); and the compound of
`formula B-7
`
`10
`
`15
`
`0
`
`/CH3
`
`F0 0
`I
`O
`
`N
`
`E]O
`
`(B-7);
`
`the compound of formula F-1
`
`

`

`IT'H
`k
`
`0
`
`7'
`
`0
`
`Cl
`
`the compound of formula F-2
`
`(F-1 );
`
`O/\CH
`
`CF2H
`
`o O
`N\H H o
`
`'1‘
`CH3
`
`(F—2);
`
`\\
`
`CH3
`
`CH3 CH3
`
`the compound of formula F-3
`
`egg—{LN
`N\N O
`/
`\
`H
`
`l
`CH3
`
`(F-3);
`
`\\
`
`F
`
`F
`
`H3
`
`5
`
`the compound of formula F-4
`
`the compound of formula F-5
`
`

`

`/
`
`N\
`H
`
`CFZH
`
`T
`CH3
`
`(F-5);
`
`\\
`
`CH3
`
`the compound of formula F-6
`
`0 No
`EFF/B: O (F-6);
`
`\
`
`\H
`
`the racemic compound of formula F—7 (trans)
`
`\\
`
`CHa
`
`CH,
`H3
`
`
`
`
`F O
`F
`
`H
`
`Ni
`
`\
`
`H“
`CH
`
`(F-7);
`
`(F-8);
`
`the compound of formula F-9
`
`

`

`(F-Q),
`
`which represents a mixture of racemic compounds of formula F—T (trans) and F-8 (cis),
`
`wherein the ratio of racemic compounds of formula F-7 (trans) to racemic compounds of
`
`formula F—8 (cis) is from 2 : 1 to 100 : 1;
`
`5
`
`a racemic compound of formula F-10 (syn)
`
`H CH3
`CH3
`H
`
`(F-10),
`
`N\
`H
`
`0
`
`\
`
`H3
`
`N l C
`
`R87
`/
`N\
`
`wherein Ra7 is trifluoromethyl or difiuoromethyl;
`
`a racemic mixture of formula F-11 (anti)
`
`H H
`
`CH3
`
`CH3
`
`(F~11).
`
`N
`\
`H
`
`0
`
`R87
`
`\
`
`N | C
`
`H
`
`3
`
`/
`N\
`
`10
`
`wherein R67 is trifluoromethyl or difluoromethyl;a compound of formula F-12
`
`O Q §T<CH3
`
`H
`
`CH3
`
`(F-12),
`
`N
`\
`H
`
`Ra?
`
`\
`
`N I C
`
`H3
`
`/
`N\
`
`

`

`which is an epimeric mixture of racemic compounds of formulae F-10 (syn) and F-11 (anti),
`
`wherein the ratio from racemic compmmds of formula F—1O (syn) ‘c racemic cmpouno‘s of
`
`formula F-11 (anti) is from 1000 : 1 to 1
`
`: 1000 and wherein Ra7 is trifluoromethyl or
`
`difluoromethyl;
`
`a compound of formula F-13
`
`N/
`
`\
`
`H
`
`_
`(F 13),
`
`10
`
`15
`
`20
`
`25
`
`wherein Rag is trifluoromethyl or difluoromethyl;
`
`trinexapac—Ethyl (841); chlormequat chloride (137); ethephon (307); prohexadione calcium
`
`(664); mepiqual chloride (509); proquinazid (682); chlorothalonil (142); famoxadone (322);
`
`fenamidone (325); benomyl (62); carbendazim (116); fuberidazole (419); thiabendazole
`
`(790); thiophanate (1435); thiophanate-methyl (802), chlozolinate (149); iprodione (470);
`
`procymidone (660); vinclozolin (849); biterlanol (84); fenarimol (327); nuarimol (587);
`pyrifenox (703); triforine (838); benalaxyl (56); furalakyl (410); metalaxyl (516); mefenoxam
`(metalaxyl-M) (517); ofurace (592); oxadixyl (601); edifenphos (290); iprobenfos (IBP) (469);
`
`isoprothiolane (474); pyrazophos (693); benodanil (896); carboxin (120); fenfuram (333);
`
`flutolanil (396); furametpyr (411); mepronil (510); oxycarboxin (608); thifluzamide (796);
`
`bupirimate (98); dimethirimol (1 082); ethirimol (1 133); diethofencarb (245); quinoxyfen (715);
`
`biphenyl (81); chloroneb (139); dicloran (240); etridiazole (321); quintozene (PCNB) (716);
`
`tecnazene (TCNB) (767); tolclofos-methyl (808); dimethomorph (263); carpropamid (122);
`
`diclocymet (237); fenoxanil (338); fthalide (643); pyroquilon (710); tricyclazole (828);
`
`fenhexamid (334); polyoxin (654); pencycuron (620); cyazofamid (185); zoxamicle (857);
`
`blasticidin-S (85); kasugamycin (483); streptomycin (744); validamycin (846); cymoxanil
`
`(200); iodocarb (3-lodo-2—propynyl butyl carbamate); propamocarb (668); prothiocarb (1361);
`
`dinocap (270); fluazinam (363); fentin acetate (347); fentin chloride; fentin hydroxide (347);
`
`oxolinic acid (606); hymexazole; octhilinone (590); fosetyl-aluminium (407); phosphoric acid;
`
`tecloftalam; triazoxide (821); flusulfamide (394); ferimzone (351); diclomezine (239);
`
`anilazine (878); arsenates; captafol (113); captan (114); chlorothalonil (142); copper (diverse
`
`salts); copper ammoniumcarbonate; copper octanoate (170); copper oleate; copper sulphate
`
`(87; 172; 173); copper hydroxide (169); dichlofluanid (230); dithianon (279); dodine (289);
`
`

`

`-7-
`
`ferbam (350); folpet (400); guazatine (422); iminoctadine (459); mancozeb (496); maneb
`(497): mercury. metiram (546); prcpineb (576); s'...'hlp':’754;) thirai'n (804), ioiyifiuanid (810);
`zineb (855); ziram (856); acibenzolar-S-methyl (6); probenazole (658); benthiavalicarb;
`benthiavalicarb—isopropyl (68); iprovalicarb (471); diflumetorim (253); ethaboxam (304);
`fiusulfamide (394); methasulfocarb (528); silthiofam (729); bacillus pumilus G834; bacillus
`
`pumilus strain QST 2808; bacillus subtiiis (50); bacilus subtilis + PCNB + metalaxyl (50; 716;
`516); cadmium chloride; carbon disulfide (945); bordeaux mixture (87); cedar leaf oil;
`
`chlorine; cinnamaldehyde; cycloheximide (1022); fenaminosuif (1144); fenamiphos (326);
`dichloropropene (233); dichlone (1052); formaldehyde (404); gliocladium virens GL-21 (417);
`glyodin (1205); hexachlorobenzene (434); iprovalicarb (471); manganous
`dimethyldithiocarbamate; mercuric chloride (511); nabam (566); neem oil (hydrophobic
`extract); oxytetracycline (611); chinomethionat (126); paraformaldehyde;
`
`pentachloronitrobenzene (716); pentachlorophenol (623); paraffin oil (628); polyoxin D zinc
`salt (654); sodium bicarbonate; potassium bicarbonate; sodium diacetate; sodium
`
`propionate; TCMTB; benalaxyl —M; boscalid (88); hexaconazole (435); metrafenone; oxine
`
`copper (605); penthiopyrad; perfurazoate; tolyfluanid; trichoderma harzianum (825);
`triphenyltin hydroxide (347); xanthomonas campestris (852); paclobutrazol (612); 1,1—bis(4—
`chIorophenyl)-2-ethoxyethanol (lUPAC-Name) (910); 2,4-dichlorophenyl benzenesulfonate
`(lUPAC- / Chemical Abstracts-Name) (1059); 2-fluoro-N—methyI-N-1—naphthylacetamide
`(lUPAC-Name) (1295); 4-chlorophenyl phenyl sulfone (lUPAC-Name) (981); abamectin (1);
`acequinocyl (3); acetoprole [CCN]; acrinathrin (9); aldicarb (16); aldoxycarb (863); alpha-
`cypermethrin (202); amidithion (870); amidoflumet [CCN]; amidothioate (872); amiton (875);
`amiton hydrogen oxalate (875); amitraz (24); aramite (881); arsenous oxide (882); AVI 382
`(compound code); AZ 60541 (compound code); azinphos-ethyl (44); azinphos-methyl (45);
`azobenzene (lUPAC-Name) (888); azocyclotin (46); azothoate (889); benomyl (62); benoxa-
`fos (alternative name) [CCN]; benzoximate (71); benzyl benzoate (lUPAC-Name) [CCN];
`bifenazate (74); bifenthrin (76); binapacryl (907); brofenvalerate (alternative name); bromo-
`cyclen (918); bromophos (920); bromophos-ethyl (921); bromopropylate (94); buprofezin
`(99); butocarboxim (103); butoxycarboxim (104); butylpyridaben (alternative name); calcium
`polysuifide (lUPAC—Name) (111); camphechlor (941 ); carbanolate (943); carbaryl (115);
`carbofuran (118); carbophenothion (947); CGA 50'439 (development code) (125); chino-
`methionat (126); chlorbenside (959); chlordimeform (964); chlordimeform hydrochloride
`(964); chlorfenapyr (130); chlorfenethol (968); chlorfenson (970); chlorfensulphide (971);
`chlorfenvinphos (131); chlorobenzilate (975); chloromebuform (977); chloromethiuron (978);
`
`1O
`
`15
`
`20
`
`25
`
`30
`
`

`

`-8-
`
`chloropropylate (983); chlorpyrifos (145); chlorpyrifos-methyl (1 46); chlorthiophos (994);
`O
`
`cinerin l (696); cinerin II (696): cinerins (696); clofentezine (15g); cg
`
`name) [CCN]; coumaphos (174); crotamiton (alternative name) [CCN]; crotoxyphos (1010);
`
`cufraneb (1013); cyanthoate (1020); cyhalothrin (196); cyhexatin (199); cypermethrin (201);
`
`DCPM (1032); DDT (219); demephion (1037); demephion-O (1037); demephion-S (1037);
`
`demeton (1038); demeton-methyl (224); demeton-O (1038); demeton—O-methyl (224);
`
`demeton-S (1038); demeton-S-methyl (224); demeton-S-methylsulphon (1039); diafen-
`
`thiuron (226); dialifos (1042); diazinon (227); dichlofluanid (230); dichlorvos (236); dicliphos
`
`(alternative name); dicofol (242); dicrotophos (243); dienochior (1071); dimefox (1081 );
`
`dimethoate (262); dinactin (alternative name) (653); dinex (1089); dinex-diclexine (1089);
`
`dinobuton (269); dinocap (270); dinocap-4 [CCN]; dinocap-6 [CCN]; dinocton (1090); dino-
`
`penton (1092); dinosulfon (1097); dinoterbon (1098); dioxathion (1102); diphenyl sulfone
`
`(lUPAC-Name) (1103); disulfiram (alternative name) [CCN]; disulfoton (278); DNOC (282);
`
`dofenapyn (1113); doramectin (alternative name) [CCN]; endosulfan (294); endothion
`
`(1121); EPN (297); eprinomectin (alternative name) [CCN]; ethion (309); ethoate-methyl
`
`(1134); etoxazole (320); etrimfos (1142); fenazaflor (1147); fenazaquin (328); fenbutatin
`
`oxide (330); fenothiocarb (337); fenpropathrin (342); fenpyrad (alternative name); fen-
`
`pyroximate (345); fenson (1157); fentrifanil (1161); fenvalerate (349); fipronil (354); fluacry-
`
`pyrim (360); fluazuron (1166); flubenzimine (1167); flucycloxuron (366); flucythrinate (367);
`
`fluenetil (1169); flufenoxuron (370); flumethrin (372); fluorbenside (1174); fluvalinate (1184);
`
`FMC 1137 (development code) (1185); formetanate (405); formetanate hydrochloride (405);
`
`formothion (1192); formparanate (1193); gamma-HCH (430); glyodin (1205); halfenprox
`
`(424); heptenophos (432); hexadecyl cyclopropanecarboxylate (lUPAC- / Chemical
`
`Abstracts-Name) (1216); hexythiazox (441); iodomethane (lUPAC-Name) (542); isocarbo-
`
`phos (alternative name) (473); isopropyl O-(methoxyaminothiophosphoryl)saiicylate
`
`(lUPAC-Name) (473); ivermectin (alternative name) [CCN]; jasmolin l (696); jasmolin II
`
`(696); jodfenphos (1248); lindane (430); lufenuron (490); malathion (492); malonoben
`
`(1254); mecarbam (502); mephosfolan (1261); mesulfen (alternative name) [CCN]; meth—
`
`acrifos (1266); methamidophos (527); methidathion (529); methiocarb (530); methomyl
`
`(531 ); methyl bromide (537); metolcarb (550); mevinphos (556); mexacarbate (1290);
`
`milbemectin (557); milbemycin oxime (alternative name) [CCN]; mipafox (1293); monocro—
`
`tophos (561); morphothion (1300); moxidectin (alternative name) [CCN]; naied (567); NC-
`
`184 (compound code); nifluridide (1309); nikkomycins (alternative name) [CCN]; nitrilacarb
`
`(1313); nitrilacarb 1:1 zinc chloride complex (1313); NNI—0101 (compound code); NNl-0250
`
`1O
`
`15
`
`20
`
`25
`
`3O
`
`

`

`-9-
`
`(compound code); omethoate (594); oxamyl (602); oxydeprofos (1324); oxydisulfoton (1325);
`
`pp'-DDT (219); parathion (615); permethrin (626); petroleum cits (alternative name) (626);
`
`phenkapton (1330); phenthoate (631); phorate (636); phosalone (637); phosfolan (1338);
`
`phosmet (638); phosphamidon (639); phoxim (642); pirimiphos-methyl (652); polychloro-
`
`terpenes (traditional name) (1347); polynactins (alternative name) (653); proclonol (1350);
`
`profenofos (662); promacyl (1354); propargite (671); propetamphos (673); propoxur (678);
`
`prothidathion (1360); prothoate (1362); pyrethrin | (696); pyrethrin ll (696); pyrethrins (696);
`
`pyridaben (699); pyridaphenthion (701); pyrimidifen (706); pyrimitate (1370); quinalphos
`
`(71 1); quintiofos (1381); R-1492 (development code) (1382); RA-17 (development code)
`
`(1383); rotenone (722); schradan (1389); sebufos (alternative name); selamectin
`
`(alternative name) [CCN]; Sl-0009 (compound code); sophamlde (1402); spirodiclofen
`
`(738); spiromesifen (739); SSl-121 (development code) (1404); sulfiram (alternative name)
`
`[CCN]; sulfluramid (750); sulfotep (753); sulfur (754); SZl-121 (development code) (757);
`
`tau-fluvallnate (398); tebufenpyrad (763); TEPP (1417); terbam (alternative name);
`
`tetrachlorvinphos (777); tetradifon (786); tetranaclin (alternative name) (653); tetrasul
`
`(1425); thiafenox (alternative name); thiocarboxime (1431); thiofanox (800); thiometon
`
`(801); thioquinox (1436); thuringiensin (alternative name) [CCN]; triamiphos (1441);
`
`triarathene (1443); triazophos (820); triazuron (alternative name); trichlorfon (824);
`
`trifenofos (1455); trinactin (alternative name) (653); vamidothion (847); vaniliprole [CCN];
`
`Yl-5302 (compound code); bethoxazin [CCN]; copper dioctanoate (IUPAC-Name)
`
`(170);copper sulfate (172); cybutryne [CCN]; dichlone (1052); dichlorophen (232); endothal
`
`(295); fentin (347); hydrated lime [CCN]; nabam (566); quinoclamine (714); quinonamid
`
`(1379); simazine (730); triphenyltin acetate (IUPAC-Name) (347); triphenyltin hydroxide
`
`(lUPAC-Name) (347); abamectin (1); crufomate (1011); doramectin (alternative name)
`
`[CCN]; emamectin (291); emamectin benzoate (291); eprinomectin (alternative name)
`
`[CCN]; ivermectin (alternative name) [CCN]; milbemycin oxime (alternative name) [CCN];
`
`moxidectin (alternative name) [CCN]; piperazine [CCN]; selamectin (alternative name)
`
`[CCN]; spinosad (737); thiophanate (1435); chloralose (127); endrin (1122); fenthion (346);
`
`pyridin-4—amine (lUPAC-Name) (23); strychnine (745); 1 —hydroxy-1 H-pyridine—Z-thione
`
`(lUPAC-Name) (1222); 4—(quinoxalin—2-ylamino)benzenesuIfonamide (lUPAC-Name) (748);
`
`8-hydroxyquinoline sulfate (446); bronopol (97); copper dioctanoate (lUPAC-Name) (170);
`
`copper hydroxide (lUPAC-Name) (169); cresol [CCN]; dichlorophen (232); dipyrithione
`
`(1 105); dodicin (1112); fenaminosulf (1144); formaldehyde (404); hydrargaphen (alternative
`
`name) [CCN]; kasugamycin (483); kasugamycin hydrochloride hydrate (483); nickel
`
`10
`
`15
`
`20
`
`25
`
`3O
`
`

`

`-10-
`
`bis(dimethyldithiocarbamate) (lUPAC-Name) (1308); nitrapyrin (580); octhilinone (590);
`
`oxolinic acid (606): oxytetracynline (61.1.); potassium hydrcxyquinoline sulfate (44G):
`
`probenazole (658); streptomycin (744); streptomycin sesquisulfate (744); tecloftalam (766);
`
`thiomersal (alternative name) [CCN]; methyl bromide (537); apholate [CCN]; bisazir
`
`(alternative name) [CCN]; busulfan (alternative name) [CCN]; diflubenzuron (250); dimatif
`
`(alternative name) [CCN]; hemel [CCN]; hempa [CCN]; metepa [CCN]; methiotepa [CCN];
`
`methyl apholate [CCN]; morzid [CCN]; penfluron (alternative name) [CCN]; tepa [CCN];
`
`thiohempa (alternative name) [CCN]; thiotepa (alternative name) [CCN]; tretamine
`
`(alternative name) [CCN]; uredepa (alternative name) [CCN]; (E)-dec-5-en-1-yl acetate
`
`with (E)-dec~5-en-1-ol (lUPAC-Name) (222); (E)-tridec-4-en-1-yl acetate (IUPAC-Name)
`
`(829); (E)—6—methylhept-2—en-4-ol (IUPAC—Name) (541); (E,Z)-tetradeca-4,10-dien—1—yl
`
`acetate (IUPAC-Name) (779); (Z)-dodec-7-en—1—yl acetate (lUPAC-Name) (285); (Z)-
`
`hexadec-11-enal (lUPAC-Name) (436); (Z)-hexadec-11-en-1-yl acetate (lUPAC—Name)
`
`(437); (Z)—hexadec-13-en-11-yn-1-yl acetate (lUPAC-Name) (438); (Z)-icos-13-en-10-one
`
`(lUPAC-Name) (448); (Z)-tetradec-7-en—1-al (lUPAC-Name) (782); (Z)-tetradec-9—en-1-ol
`
`(lUPAC-Name) (783); (Z)-tetradec-9-en-1-yl acetate (lUPAC-Name) (784); (7E,92)—dodeca—
`
`7.9-dien-1—yl acetate (lUPAC-Name) (283); (92,11E)-tetradeca-9,1 1-dien-1-yl acetate
`
`(iUPAC-Name) (780); (92,12E)—tetradeca-9,12-dien-1-yl acetate (lUPAC-Name) (781); 14-
`
`methyloctadec—1-ene (lUPAC-Name) (545); 4-methylnonan-5-ol with 4-methylnonan-5-one
`
`(lUPAC-Name) (544); alpha-multistriatin (alternative name) [CCN]; brevicomin (alternative
`
`name) [CCN]; codlelure (alternative name) [CCN]; codlemone (alternative name) (167);
`
`cuelure (alternative name) (179); disparlure (277); dodec-8—en—1-yl acetate (lUPAC—Name)
`
`(286); dodec—9-en-1—yl acetate (lUPAC—Name) (287); dodeca-8,10-dien—1—y| acetate (IUPAC-
`
`Name) (284); dominicalure (alternative name) [CCN]; ethyl 4-methyloctanoate (IUPAC-
`
`Name) (317); eugenol (alternative name) [CCN]; frontalin (alternative name) [CCN];
`
`gossyplure (alternative name) (420); grandlure (421); grandlure l (alternative name) (421);
`
`grandlure ll (alternative name) (421); grandlure lll (alternative name) (421); grandlure IV
`
`(alternative name) (421); hexalure [CCN]; ipsdienol (alternative name) [CCN]; ipsenol
`
`(alternative name) [CCN]; japonilure (alternative name) (481 ); lineatin (alternative name)
`
`[CCN]; litlure (alternative name) [CCN]; looplure (alternative name) [CCN]; medlure [CCN];
`
`megatomoic acid (alternative name) [CCN]; methyl eugenol (alternative name) (540);
`
`muscalure (563); octadeca-2,13-dien-1-yl acetate (IUPAC-Name) (588); octadeca-3.13-dien-
`
`1-yl acetate (lUPAC-Name) (589); orfralure (alternative name) [CCN]; oryctalure
`
`(alternative name) (317); ostramone (alternative name) [CCN]; siglure [CCN]; sordidin
`
`1O
`
`15
`
`20
`
`25
`
`30
`
`

`

`-11-
`
`(alternative name) (736); sulcatol (alternative name) [CCN]; tetradec—11-en-1-yl acetate
`
`(IUPAC-Name) (785); trimedlure (839); trimedlure A (alternative name) (639); 'uimeu'iure 81
`
`(alternative name) (839); trimedlure B2 (alternative name) (839); trimedlure C (alternative
`
`name) (839); trunc—call (alternative name) [CCN]; 2—(octylthio)ethanol (lUPAC-Name) (591);
`
`butopyronoxyl (933); butoxy(polypropylene glycol) (936); dibutyl adipate (lUPAC—Name)
`
`(1046); dibutyl phthalate (1047); dibutyl succinate (lUPAC-Name) (1048); diethyltoluamide
`
`[CCN]; dimethyl carbate [CCN]; dimethyl phthalate [CCN]; ethyl hexanediol (1137); hexamide
`
`[CCN]; methoquin-butyl (1276); methylneodecanamide [CCN]; oxamate [CCN]; picaridin
`
`[CCN]; 1,1-dichloro-1-nitroethane (IUPAC— / Chemical Abstracts-Name) (1058); 1,1—dichloro-
`
`2,2—bis(4-ethylphenyl)ethane (lUPAC-Name) (1056); 1,2-dichloropropane (lUPAC-l
`
`Chemical Abstracts—Name) (1062); 1,2-dichloropropane with 1.3-dichloropropene (IUPAC-
`
`Name) (1063); 1-bromo—2-chloroethane (IUPAC- / Chemical Abstracts-Name) (916); 2,2,2-
`
`trichloro-1-(3,4-dichlorophenyl)ethyl acetate (lUPAC-Name) (1451); 2,2—dichlorovinyl 2-ethyl-
`
`sulfinylethyl methyl phosphate (lUPAC-Name) (1066); 2-(1,3-dithiolan-2—yl)phenyl dimethyl—
`
`carbamate (IUPAC- / Chemical Abstracts-Name) (1109); 2-(2-butoxyethoxy)ethyl thiocyanate
`
`(IUPAC- / Chemical Abstracts-Name) (935); 2-(4.5-dimethyl-1,3—dioxolan-2—yl)phenyl
`
`methylcarbamate (IUPAC- / Chemical Abstracts-Name) (1084); 2-(4-chloro-3,5—xylyloxy)—
`
`ethanol (lUPAC-Name) (986); 2-chlorovinyl diethyl phosphate (lUPAC-Name) (984); 2-
`
`imidazolidone (lUPAC-Name) (1225); 2—isovalerylindan—1,3-dione (lUPAC—Name) (1246); 2-
`
`methyl(prop-2—ynyl)aminophenyl methylcarbamate (lUPAC-Name) (1284); 2-thiocyanatoethyl
`laurate (lUPAC—Name) (1433); 3—bromo-1-chloroprop-1-ene (lUPAC-Name) (917); 3-methyl—
`1-phenylpyrazol-5-yl dimethylcarbamate (lUPAC—Name) (1283); 4-methyl(prop-2-ynyl)amino-
`3,5—xylyl methylcarbamate (lUPAC-Name) (1285); 5,5-dimethyl-3-oxocyclohex-1-enyl
`dimethylcarbamate (lUPAC~Name) (1085); abamectin (1); acephate (2); acetamiprid (4);
`acethion (alternative name) [CCN]; acetoprole [CCN]; acrinathrin (9); acrylonitrile (IUPAC-
`
`Name) (861); alanycarb (15); aldicarb (16); aldoxycarb (863); aldrin (864); allethrin (17);
`
`allosamidin (alternative name) [CCN]; allyxycarb (866); alpha-cypermethrin (202); alpha-
`
`ecdysone (alternative name) [CCN]; aluminium phosphide (640); amidithion (870);
`
`amidothioate (872); aminocarb (873); amiton (875); amiton hydrogen oxalate (875); amitraz
`
`(24); anabasine (877); athidathion (883); AV! 382 (compound code); AZ 60541 (compound
`
`code); azadirachtin (alternative name) (41); azamethiphos (42); azinphos-ethyl (44);
`
`azinphos-methyl (45); azothoate (889); Bacillus thuringiensis delta endotoxins (alternative
`
`name) (52); barium hexafluorosilicate (alternative name) [CCN]; barium polysulfide (IUPAC-
`/ Chemical Abstracts-Name) (892); barthrin [CCN]; BAS 320 l (compound code); Bayer
`
`10
`
`15
`
`20
`
`25
`
`30
`
`

`

`-12-
`
`22/190 (development code) (893); Bayer 22408 (development code) (894); bendiocarb (58);
`
`benfuracarb (60); bensultap (66); beta—cyfluthrin (1.94); beta—cypermethrin (203); bifcnthrin
`
`(76); bioallethrin (78); bioallethrin S-cyclopentenyl isomer (alternative name) (79);
`
`bioethanomethrin [CCN]; biopermethrin (908); bioresmethrin (80); bis(2-chloroethyl) ether
`
`(lUPAC-Name) (909); bistrifluron (83); borax (86); brofenvalerate (alternative name);
`
`bromfenvinfos (914); bromocyclen (918); bromo-DDT (alternative name) [CCN]; bromophos
`
`(920); bromophos-ethyl (921); bufencarb (924); buprofezin (99); butacarb (926); butathiofos
`
`(927); butocarboxim (103); butonate (932); butoxycarboxim (104); butylpyridaben (alternative
`
`name); cadusafos (109); calcium arsenate [CCN]; calcium cyanide (444); calcium polysulfide
`
`(lUPAC-Name) (111); camphechlor (941); carbanolate (943); carbaryl (115); carbofuran
`
`(118); carbon disulfide (lUPAC- / Chemical Abstracts-Name) (945); carbon tetrachloride
`
`(lUPAC—Name) (946); carbophenothion (947); carbosulfan (119); cartap (123); cartap
`
`hydrochloride (123); cevadine (alternative name) (725); chlorbicyclen (960); chlordane
`
`(128); chlordecone (963); chlordimeform (964); chlordimeform hydrochloride (964);
`
`chlorethoxyfos (129); chlorfenapyr (130); chlorfenvinphos (131); chlorfluazuron (132);
`
`chlormephos (136); chloroform [CCN]; chloropicrin (141); chlorphoxim (989); chlorprazophos
`
`(990); chlorpyrifos (145); chlorpyrifos-methyl (146); chlorthiophos (994); chromafenozide
`
`(150); cinerin | (696); cinerin II (696); cinerins (696); cis-resmethrin (alternative name);
`
`cismethrin (80); clocythrin (alternative name); cloethocarb (999); closantel (alternative
`
`name) [CCN]; clothianidin (165); copper acetoarsenite [CCN]; copper arsenate [CCN];
`
`copper oleate [CCN]; coumaphos (174); coumithoate (1006); crotamiton (alternative name)
`
`[CCN]; crotoxyphos (1010); crufomate (1011); cryolite (alternative name) (177); CS 708
`
`(development code) (1012); cyanofenphos (101 9); cyanophos (184); cyanthoate (1020);
`
`cyclethrin [CCN]; cycloprothrin (188); cyfluthrin (193); cyhalothrin (196); cypermethrin (201);
`
`cyphenothrin (206); cyromazine (209); cythioate (alternative name) [CCN]; d—Iimonene
`
`(alternative name) [CCN]; d-tetramethrin (alternative name) (788); DAEP (1031); dazomet
`
`(216); DDT (219); decarbofuran (1034); deitamethrin (223); demephion (1037); demephion-
`
`O (1037); demephion-S (1037); demeton (1038); demeton-methyl (224); demeton-O (1038);
`
`demeton—O-methyl (224); demeton-S (1038); demeton-S-methyl (224); demeton-S-
`
`methylsulphon (1039); diafenthiuron (226); dialifos (1042); diamidafos (1044); diazinon
`
`(227); dicapthon (1050); dichlofenthion (1051 ); dichlorvos (236); dicliphos (alternative
`
`name); dicresyl (alternative name) [CCN]; dicrotophos (243); dicyclanil (244); dieldrin
`
`(1070); diethyl 5-methylpyrazol-3-yl phosphate (lUPAC-Name) (1076); diflubenzuron (250);
`
`dilor (alternative name) [CCN]; dimefluthrin [CCN]; dimefox (1081); dimetan (1085);
`
`10
`
`15
`
`20
`
`25
`
`30
`
`

`

`-13-
`
`dimethoate (262); dimethrin (1083); dimethylvinphos (265); dimetilan (1086); dinex (1089);
`\-
`u IUIsauna
`‘I
`‘.-......,,—..
`uivuvu\lv
`u
`|
`(I:
`’174
`I},
`3Mn
`A:n A‘IH‘I nnl
`dinex-diciexine(1089);r_llngp_rgn(1no'z\-(45.19539... 1.994 )
`A». Mn 95
`.
`);
`1
`diofenolan (1099); dioxabenzofos (1100); dioxacarb (1101); dioxathion (1102); disulfoton
`(278); dithicrofos (1 108); DNOC (282); doramectin (alternative name) [CCN]; DSP (1115);
`ecdysterone (alternative name) [CCN]; El 1642 (development code) (1118); emamectin
`(291); emamectin benzoate (291); EMPC (1120); empenthrin (292); endosulfan (294);
`endothion (1121); endrin (1122); EPBP (1123); EPN (297); epofenonane (1124); epri-
`
`nomectin (alternative name) [CCN]; esfenvalerate (302); etaphos (alternative name)
`[CCN]; ethiofencarb (308); ethlon (309); ethiprole (310); ethoale-methyl (1134); ethoprophos
`(312); ethyl formate (lUPAC-Name) [CCN]; ethyl—DDD (alternative name) (1056); ethylene
`dibromide (316); ethylene dichloride (chemical name) (1136); ethylene oxide [CCN]; etofen-
`prox (319); etrimfos (1142); EXD (1143); famphur (323); fenamiphos (326); fenazaflor
`(1147); fenchlorphos (1148); fenethacarb (1149); fenfluthrin (1150); fenitrothion (335); feno-
`bucarb (336); fenoxacrim (1153); fenoxycarb (340); fenpirithrin (1155); fenpropathrin (342);
`fenpyrad (alternative name); fensulfothion (1 1 58); fenthion (346); fenthion—ethyl [CCN]; fen-
`valerate (349); fipronil (354); flonicamid (358); flucofuron (1168); flucycloxuron (366); flu-
`cythrinate (367); fluenetil (1169); flufenerim [CCN]; flufenoxuron (370); flufenprox (1171);
`flumethrin (372); fluvaiinate (1184); FMC 1137 (development code) (1185); fonofos (1191);
`formetanate (405); formetanate hydrochloride (405); formothion (1192); formparanate
`(1193); fosmethilan (1194); fospirate (1195); fosthiazate (408); fosthietan (1196); furathio-
`carb (412); furethrin (1200); gamma-cyhalothrin (197); gamma-HCH (430); guazatine (422);
`guazatine acetates (422); GY-81 (development code) (423); halfenprox (424); halofenozide
`(425); HCH (430); HEOD (1070); heptachlor (1211); heptenophos (432); heterophos [CCN];
`hexaflumuron (439); HHDN (864); hydramethylnon (443); hydrogen cyanide (444); hydro—
`prene (445); hyquincarb (1223); imidacloprid (458); imiprothrin (460); indoxacarb (465); IPSP
`(1229); isazofos (1231 ); isobenzan (1232); isocarbophos (alternative name) (473); isodrin
`(1235); isofenphos (1236); isolane (1237); isoprocarb (472); isopropyl O-(methoxyaminothio—
`phosphoryl)salicylate (lUPAC-Name) (473); isoprothiolane (474); isothioate (1244);
`isoxathion (480); ivermectin (alternative name) [CCN]; jasmolin I (696); jasmolin ll (696);
`jodfenphos (1248); juvenile hormone | (alternative name) [CCN]; juvenile hormone ll
`(alternative name) [CCN]; juvenile hormone lll (alternative name) [CCN]; kelevan (1249);
`kinoprene (484); lambda-cyhalothrin (198); lead arsenate [CCN]; leptophos (1250); lindane
`(430); lirimfos (1251); lufenuron (490); lythidathion (1253); m-cumenyl methylcarbamate
`(lUPAC-Name) (1014); magnesium phosphide (lUPAC-Name) (640); malathion (492);
`
`1O
`
`15
`
`20
`
`25
`
`30
`
`

`

`-14-
`
`malonoben (1254); mazidox (1255); mecarbam (502); mecarphon (1258); menazon (1260);
`_L.-‘_
`ICLGIH‘
`
`mephosfolan (1261): mercurous chloride (51.3); mesulfenfcs (1253); meta. . (513); -
`
`potassium (alternative name) (519); metam—sodium (519); methacrifos (1266);
`
`methamidophos (527); methanesulfonyl fluoride (IUPAC- / Chemical Abstracts-Name)
`(1268); methidathion (529); methiocarb (530); methocrotophos (1273); methomyl (531);
`methoprene (532); methoquin-butyl (1276); methothrin (alternative name) (533);
`
`methoxychlor (534); methoxyfenozide (535); methyl bromide (537); methyl isothiocyanate
`
`(543); methylchloroform (alternative name) [CCN]; methylene chloride [CCN]; metofluthrin
`[CCN]; metolcarb (550); metoxadiazone (1288); mevinphos (556); mexacarbate (1290);
`milbemectin (557); milbemycin oxime (alternative name) [CCN]; mipafox (1293); mirex
`(1294); monocrotophos (561); morphothion (1300); moxidectin (alternative name) [CCN];
`naftalofos (alternative name) [CCN]; naled (567); naphthalene (lUPAC- / Chemical
`Abstracts-Name) (1303); NC-170 (development code) (1306); NC-184 (compound code);
`nicotine (578); nicotine sulfate (578); nifluridide (1309); nitenpyram (579); nithiazine (1311);
`nitrilacarb (1313); nitrilacarb 1:1 zinc chloride complex (1313); NNI-0101 (compound code);
`NNl-0250 (compound code); nornicotine (traditional name) (1319); novaluron (585); novi-
`flumuron (586); 0-2,5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (lUPAC-Name)
`(1057); 0,0-diethyl O—4-methyl—2-oxo-2H—chromen-7-yl phosphorothioate (lUPAC-Name)
`(1074); 0,0-diethyl 0-6-methyI—2-propylpyrimidin-4—yl phosphorothioate (lUPAC-Name)
`(1075); 0,0,0',O'-tetrapropyl dithiopyrophosphate (lUPAC-Name) (1424); oleic acid (IUPAC-
`Name) (593); omethoate (594); oxamyl (602); oxydemeton-methyl (609); oxydeprofos
`(1324); oxydisulfoton (1325); pp'-DDT (219); para-dichlorobenzene [CCN]; parathion (615);
`parathion-methyl (616); penfluron (alternative name) [CCN]; pentachlorophenol (623); pen-
`tachlorophenyl laurate (lUPAC-Name) (623); permethrin (626); petroleum oils (alternative
`name) (628); PH 60-38 (development code) (1328); phenkapton (1330); phenothrin (630);
`phenthoate (631); phorate (636); phosalone (637); phosfolan (1338); phosmet (638); phosni—
`chlor (1339); phosphamidon (639); phosphine (lUPAC-Name) (640); phoxim (642); phoxim-
`methyl (1340); pirimetaphos (1344); pirimicarb (651 ); pirimiphos—ethyl (1345); pirimiphos-
`
`methyl (652); polychlorodicyclopentadiene isomers (lUPAC-Name) (1346); polychloroter-
`
`penes (traditional name) (1347); potassium arsenite [CCN]; potassium thiocyanate [CCN];
`prallethrin (655); precocene I (alternative name) [CCN]; precocene il (alternative name)
`[CCN]; precocene lll (alternative name) [CCN]; primidophos (1349); profenofos (662); pro-
`fluthrin [CCN]; promacyl (1354); promecarb (1355); propaphos (1356); propetamphos (673);
`propoxur (678); prothidathion (1360); prothiofos (686); prothoate (1362); protrifenbute
`
`1O
`
`15
`
`20
`
`25
`
`30
`
`

`

`-15-
`
`[CCN]; pymetrozine (688); pyraclofos (689); pyrazophos (693); pyresmethrin (1367); pyre-
`
`thrin | (696): pyrethrin ll (696); nyrethrins (696); pyridaben (599); pyridal,l (700); pyrida phen—
`
`thion (701); pyrimidifen((706); pyrimitate (1370); pyriproxyfen (708); quassia (alternative
`
`name) [CCN]; quinalphos (711); quinalphos-methyl (1376); quinoth