Note: Descriptions are shown in the official language in which they were submitted.
r ~ _~
.~,..... .
~o47~B5
~ The present invention relates to organic phosphoric
. .,
~; acid esters, processes for their manufacture, and to their
use in pest control.
:
~ The compounds have the formula
...~,
,~,:
~ .,
~s,' ~
. .
; ~ N=N ~ ~ O P / I (I)
(R4)m (R3)n
wherein Rl and R2 each represents alkyl with 1 to 5 carbon
atoms, R3 and R4 each represents halogen or alkyl with 1 to
5 carbon atoms, X represents oxygen or sulphur, n is zero or
a number from 1 to 4, and m is zero or a number from 1 to 5.
:.,
By halogen is meant fluorine, chlorine, bromine, or
iodine, but especially chlorine or bromine.
~'
i The alkyl group Rl to R4 can be straight-chain or branched.
:
Examples of such groups include: methyl, ethyl, propyl, iso-
~;~ propyl, n-, i-, sec.- and tert.-butyl, n-pentyl and isomers
thereof.
:
'':
~ - 2 -
.:
, , , ~ ~, : . : ,
The compounds ~ ~7 ~ormula I are manufactured by the
following known methods:
'~ S X
la) ~ P-~Ial. + ~IO ~ ~ -N--~T ~ d--~ç-ce~t--or~ > I
(Il) (R3)n (R4)m
~(III)
S X
Rl~\ 11
lb)R20~> + MeO~3N=N~
(IV)
, X
;, Ha.l~ ~ N=N ~ ~ VI ~ :
- (v)(R3)n ( )R4)m 1-
X
R2~ 11 0 ~ \ ~==~ + HYR ~ :
Hal ~ ~ -N=N ~ (VII)
s - -- -- - ---~ I
~ (R3)n( 4)m ~ M~Rl
¦ (VI)(VIII)
..
; .
~ In the formulae II to VIII, to R4, n and m have the
: meanings given for the formula I, Hal represents a halogen
atom, in particular chlorine J and Me represents an alkali metal,
-. especially sodium or potassium, an ammonium or alkylammonium
group.
- 3 -
. . . - . .
. ~
n47~89
Suitable acid acceptors are: tertiary amlnes, e.g. trial-
kylamine, pyridine~ dialkyl anilines; inorganic bases, e.g.
hydrides, hydroxides; carbonates and bicarbonates o-f alkali
metals and alkaline earth metals. It is sometimes necessary
to use catalysts in the reac~ions, for example copper or copper
chloride. Processes laJ lb, and 2 are carried out at a reac-
tion temperature between -2C and 130''C, at normal pressure,
and in solvents or diluents.
Examples of suitable solvents or diluents are: e~her and
ethereal compounds, e.g. diethyl e~her, dipropyl ether, dioxan
tetrahydrofuran; amides, e.g. N,N-dialkylated carboxylic acid
amides; aliphatic, aromatic, and halogenated hydrocarbons, in
~.
particular benzene, tuolene, xyleneJ chloroform, chloroben~ene;
nitriles, e.g. acetonitrile; dimethyl sulphoxide; ketones,
e.g. acetone,methyl ethyl ketone; water.
The starting materials of the formulae II, III, IV, V, VII,
and VIII can be manufactured in an~logous ~anner to known
methods.
The compounds of the formula I have a broad biocidal act-
ivity spectrum and can therefore be used for combating various
plant and animal pests. In particular they are suitable for
combating insects of the families: Acrididae, Blattidae,
~r~oc-
10 ~ . Gryllidae, Gryllotalpidae, Tettigoniidae, Cimicidae, PLl~rrhoc
oridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseu-
doccidae, Chrysomalidae, Coccinellidae, Bruchidae, Scara~aei-
dae, Dermestidae, Tenebrionidae, Curcu ionidae, Tineidae,
Noctuidae, Lymantriidae, Pyralidae, Galleriidae, Culicidae,
Tipulidae, Stomoxydae, Musci~ae, Calliphoridae, Trypetidae,
., ,
_ 4
047489
Pulicidae J as well as Acaridae of the families: Ixodidae,
Argasidae 9 Tetranychidae, Dermanyssidae. ~ -
By addit;on of other insecticides and/or acaricides it ~ -
- is possible to improve substan~ially the insecticidal or
acaricidal action and to adapt it to given circumstances.
The follo~Jing active substances are examples of suitable
~, ,
additives:
. .
r,
~ Bis-O,O-diethylphosphoric aci.d anhydride (lEPP)
:. - , .
Dimethyl-(2,2,2-trichloro-1-hy(lroxyetllyl)-phosphonate ~' ~
j~,
(TRICHLORFON)
. 1,2-dibromo-2,2-dichloroethyldimethylphosphate (N~LED)
.;,~ . ~
si 2,2-dichlorovinyldimethylphosphate (DICHLORVOS)
2-methoxycarbamyl-1-methylvinyldimethylphospha~e (MEVINPHOS)
Dimethyl-l-methyl-2-(methylcarbamoyl~vinylphosphate cis
(MONOCROTOPHOS)
3-(dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide
(DICROTOPHOS)
2-chloro-2-diethylcarbamoyl-1-methylvinyldimethylphosphate
(PHOSPHAMIDON)
,~
O,O-diethyl-O(or S)-2-(ethylthio)-ethylthiophosphate (DEMETON)
~; S-ethylthioethyl-O,O-dimethyl-dithiophosphate (THIOMETON)
, .
O,O-diethyl-S-ethylmercaptomethyldithiophosphate (PHORATE)
s O,O-diethyl-S-2-(ethylthio)ethyldithiophosphate (DISULFOTON)
'' - '
,
- 5 -
.
~(~47489
0,0-dime~hyl-S-2-(e~hylsulphinyJ)e~hy].~hi.ophosphate
(OXYDEMI~ TON l ~ETllYI,)
0,0-dimetllyl-S-(].,2-(llcarbel:hoxyethy].di.t:hi,ol)hosphate
(MALATITI ON )
O,O~O,O- tetraethyl-S,S' -methy1ene-bis-dithiol)hosphate (ET~IION)
O-ethyl-S,S-dipropyldithiopllosphate
O,O-clime~hyl-S (N-methyl-N-formylcarbamoylmetllyl)-dithio~ os-
phate ~FORMOTIIION)
O,O-dimethyl S-(N-met:hy].carbamoy].me~hyl)-dithiophosphate
..
~!)IME~TlloATE)
O,O-dimethyl-O-p nitrophenylthiophosphate (P.ARATllION-I`~THYL)
O,O-diethyl-O-p-nitrophenylthiophosphate (PARATHION)
O~ethyl-O-p-nitrophenylphenylthiophosphate (EPN)
0,0-dimethyl-0-(4-nitro-m-tolyl)-thiophosphate (FENITnOTHION)
- 15 O,O-dimethy1-0-2,4,5-~rich10ropheny1thiophosphate (P~ONNEL)
O ethyl-0-2,4,5-trichlorophenylethyl~hiophosphate (TRICHLORO-
NATE)
0,0-dimethyl-0-2,5-dichloro-4-bromophenylthiophosphate
- (BRO~OPHOS) - -
0,0-dimethyl-0-(2,5-dichloro-4-iodophenyl)-thiophosphate
(JODOFENPHOS)
4-tert.butyl-2-chlorophenyl-N-me~hyl-O-methylamidophosphate
(CRUFO~ATE)
0,0-dimethyl-0-(3-methyl-4-methylmercaptophenyl)-thiophosphate
(FENTlIION)
:
,
, .
.- ~ ,
"''' ~ " '` ~0474ss
v
Xsopropylalnino-O-ethyl-O-(4-lne~ ylmercapto-3-mct:llylphenyl)- ''
,. ~ phosphate :,
',, O,O-dieLhyl-O-p-(metllylsulphirlyl)phenyl-l::hiopllosphate
(]~ENSULFOTIIION)
5 . o-p-(dilrlelllylsulphamido)-pllellyl-o~o-dillle~Lhylthiophospha1~e
c~ (FAilPHUR)
v O,O,O',O'-tetramethyl-O,O'-thiodi-p-phenylenethiophosphate
r,., ~ .
.~,. O-ethyl-S-pllenyl-ethyldithiopllosphate
,. 0,0-dimethyl-0-(a-1nethylbenzyl-3-hydroxycrotonyl)phosphate
. 10 2-chloro-1-(2,4 dichlorophenyl)vinyl-diet:hylpllosphate
. (CI~LORFE:NVINPIIOS)
..
i l-chloro-1--(2,4,5-trichlorophenyl)vinyl-dimethylphosphate
0-~2-chloro-1-(2,5-dichlorophenyl)]vinyl-O,O-diethylthio-
phosphate
.;i 15 Phenylglyoxylonitriloxime-O,O-diethylthiophosphate (PHOXIM)
i::! O,O-diethyl-O-(3-chloro-4-methyl-2-oxo-2-H-l-benzopyran-7-yl)-
. thiophosphate (COUMAPHOS)
2,3-p-dioxandithiol-S~S-bis(O,O-diethyldithiophosphate) ~.
(DIOX~THION)
5-[(6-chloro-2-oxo-3-benzoxazolinyl)methyl]O,O-diethyldithio-
phosph~te (PIIOSALONE)
2~(diethoxyphosphinylimino)-1,3-dithiolane
. - O,O-dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5-(4H)-onyl-(4)-
- methyl]dithiophosphate
Z5 O,O-dimethyl-9-phthalimidomethyl-dithiopllosphate (IMIDAN)
~ . ,
_ 7 _ ,~
, . i
,.
.-- . .
47~89
O~o-diet~ o~(3~5~6-l~r:i-chloro-2-py~-idyl)l~hio~ os~ at:e
O,O-di.e~hyl O-~-pyra~inyl~hiophosplla~e (THION~ZIN)
~' 0,O~dic~hyl-0-(2-isopropyl-4-me~hyl-6-pyriT:liclyl)t:hiophosphate
(DIA~XNON)
0,0-di.ethyl-0-(2-quinoxalyl)thiophosphatè
0,0-dimethyl-S-~4-oxo-1,~,3-benzotria~in~3(4I-I)-ylTnethyl)-
dithiophospllate (A%INPI~OS~THYL)
0,0-dicthyl-S-(4-oY~o-1,2,3-benzotriazin-3(~II)-ylmethyl)- -
dithiophosphate (AZINPHOSETllYL)
S [(4,6-diamino-s triazill-2-yl)rnethyl]-0,0-dimethyldit:hio-
. phosphate (ME.NAZON) .;
j' O,O-dimethyl-O (3-chloro-4-nitrophenyl)thiophosplate
` (CllLORTlIION)
'' O,O-dimethyl-O(or S)-2-(etllylthioethyl)thiophosl)hate
15 (DE~ETON-S-METHYL)
2~(0~0-dimethyl-phosphoryl-thiomethyl)-5-methoxy-pyrone- --
4-3,4-dichloroben~yl-triphenylphosphoniumchloride :.
0,0-diet:hyl-S-(2,5-dichlorophenylthiomethyl)dithiophosphate ' ~-' .
(PHENKAPTON) . :. .
0,0-diethyl-0-(4-methyl-cumarinyl-7`-~hiophosphate (POTASAN)
$-amino bis(dimethylami~o)phosphinyl-3-phenyl-1,2,4-triazole
(TRI~MIP~IOS)
N-methyl-5-(0,0-dimethylthiolphosphoryl)-3-thiavaleramide
~VAMIDOTHION)
0,0-diethyl-0-12-dimethylamino-4-methylpyrimidyl-(6)]-thio- .
phosphate (DIOCTHYL)
- 8 -
; . .. .
, .
'
, ,.. ,, ., --.. ....... .
.
- ~47489
O, O - di.methy].-S - (methy] carbalnoy1me l:hyl) - 1 hi.ophospllat:e (O`IETI~Ol~TE)
i~ O -~thy1-0 - (8- quino:l i.nyl) -plleny1t~ iophosr)llonatc! (OXINOTIIIOPIIO.S)
O~ etllyl-S~Illethyl--ar~ lothiophosphate (I:~ONITOR)
O-methyl-O- (2,5-dichloro--4-bromoplleny:l.)-bellzoth;.ophosphate
` 5 (~IIOSVEL)
O,O,O~O-tetrapropyldithiophospha~e
3-(dimethoxyphosphlnyloxy)-N-methyl-N-methoxy-cis-crotonarnide
O,O--dimethyl-S-(N-ethylcarbamoylmethyl)ditlliopllosphate
(ETI-lOATE-~lETHYL)
O,O-diethyl-S-(N-isopropylcarbamoylme~hyl)-di.thiophos~ ate
(l'ROTllOATE)
S-N--(l-cyano-l-methylethyl)carbalnoylmetllylcliethyl~hiolphosplla~e
(cyANTlloATE:)
S-(2-acetamidoethyl)-0,0-dimethyldithiophosphate - ~-
~lexamethylphosphoric acid triamide (llE~fPA)
0,0-dimethyl-O-(2-chloro-4-nitrophenyl,)thi.ophosphate
(DICAPTHON)
O,O-dimethyl-O-p-cyanophenyl thiophosphate (CYANOX)
O-ethyl-O-p-cyanophenylthiophosphonate
0,0-diethyl-0-2,4-dichlorophenylthiophosphate (DICHLOR~ENTHION)
- 0-2,4-dichlorophenyl-0-methylisopropylamidothiophosphate
0,0-diethyl-0-2,5-dichloro-4-bromophenylthiophospllate
(BROMOP~lOS-ETI~L)
- dimethyl-p-(methylthio)phenylphosphate
O,O-dimethyl-O-p-sulphamidophenylthiophosphate
_9 _ ; ~
~ ., . _ _ _.. _ . _- ..... , .. . _ . _.. _ _. . _.. . .. .... . . ... ...... ....... ...... ......... ..
~(~474S9
O-~p- (p-chlorophel~y'l)-azophenyl~O,O d:imel,lly].thi,opllosphate
(AY~OTI-IOI~TE )
O-et~llyl--S -4-chlorophenyl-ethylditlliopl~ospllate
O-isol~u~yl-S-p-clllorophenyl-ethylditlli.opllosplla~e
O,O dimethyl-S-p-chloropllenyl~hiophosphaLe :~
O,O-dimethyl-S-(p-chlorophenyl~hiomethyl)d:ithiophospllate
O,O-di.ethyl p-clllorophenylmercaptomethyl-dithiophosphate
(CARP.OPHEI~OTIIION)
O,O-die~hyl-S~p-chlorophenylthiome~hyl-thi.opllosphate :~'
. ~ .
,: 10 O,O-dimethyl-S-(carbethoxy-phenylm2l::1lyl)dithiophosphate
(PHE~lTHOATE)
` O,O-diethyl-S-(carbofluorethoxy~phenylmethyl)-ditlliophosphate
:~ O,O-dimethyl S-carboisopropoxy-phenylmethyl)-dithiophosphate
; 0,0--diethyl-7-hydroxy-3,4-tetramethylene-coumarinyl-thiophos-
phate (COUMITHOATE)
2-me~hoxy-4-H~1,3,2-benzodio~aphosphorin-2-sulphide
0,0-diethyl-0-(5-pllenyl-3-i.sooxazolyl)thiophosphate
: 2-(diethoxyphosphinylimino)-4-methyl-1,3-dithiolane
tris-(2~methyl-1-aziridinyl)-phosphine oxide (METEPA)
S-(2-chloro-1-phthalimidoethyl)-0,0-diethyldi~hiophospllate
N-hydroxynaphthalimido-diethylphosphate
. dimethyl-3,5,6-trichloro-2-pyridylphosphate -
. :
.. 0,0-dimethyl-0-(3,5,6-trichloro-2-pyridyl)thiophosphate
S-2-(ethylsulphonyl)ethyl dimethylthiolphosphate
(DIOXYDE~TON-S-METHYL)
., ,
:
- 10 - - -
., .
.. ,, .. _ .. , ., . ... , .. , .. .. , . . , .. _., ., _,,, , ., . .. , _.. _.. . ~ .. ... , .. ,.. , .. ,,, . , _,, . .. , .
... ...... :.. . ..... . . ... . . .
047489
'i. dietllyl-s-2-(e~:hylsu~ inyl)eL:llyl di.th-i.opllosphate
(O~I~LSULFOlON)
l~is--O~O-di.e~llylthi.opllosphoric acid ankyclride (SULIOTEP)
- di.methyl-1,3-di(carbomethoxy)-1-pro~en-2-yl-phosphate
dimetllyl-(2,2,~- trichloro-l-butyroyloxyethyl)phosphate
(BUTONATE)
-~ 0,O~dimethyl-0-(2,2-dicllloro-1-methoxy-vinyl)phospllate
bis-(dimethylamido)~luorpllosphate (DIMEFOX)
3,~-dichlorobenzyl-triphenylphosphoniumchloride
.,' 10 dimethyl-N-met:hoxymet~hylcarbamoylmethyl-dil:lliophosphate
(FORMOCARB~M)
O,O-die~-hyl-O (2,2 dichloro-l-chloroe~hoxyvinyl)-pllosphate
0,0-dime~hyl-0-(2,2-dichloro-1-chloroetlloxyvinyl)-phosphate
O-ethyl-S,S-diphenyldithiolphosphate
O-ethyl-S-benzyl-phenyldithiophosphonate
0,0 diethyl-S-benzyl-thiolphospllate ' ' ',
0,0-dimethyl-S-(4-ehlorophenylthiomethyl)dithiophosphate
(METI-~LCARBOPHENOTHION)
. O,O-dimethyl-S-(ethylthiomethyl)dithiophosphate
diisopropylaminofluorophosphate (MIPAFOX)
O,O-dimethyl-S-(morpholinylcarbamoylmethyl)dithiophosphate
(MORPIIOTHION)
bismethylamido-phenylphosphate
O,O-dimethyl-S~(benzenesulphonyl)dithiophosphate
2~ . O,O-dimethyl-(S and O)-ethylsulphinylethylthiophosphate
.
- 11 - - .
`~ ~047~ss
0,0-diethyl-0-4 nit~ophenylphospllat~e
triethoxy--isopropoxy-bis(thiophospllirlyl)disulpllide
2-me~hoxy-4H-1,3,2-benzodio~aphosphorin-2 oxide
octamethylpyrophosphoramide (SC~ ~ DAN)
bis-(dimcthoxy~hiophosphinylsulphido)-phenylmethane
N,N,N',N'-tetrame~hyldiamidofluorophosphate (DIMEFOX)
O-phenyl O-p nitrophenyl-me~hanethlophosphonate (COJ~.P)
O-methyl-0-(2-chloro-4-tert butyl-phenyl)-N-methylamidothio-
phosphate (~ARL~NE)
0-ethyl-0-(2,4-dichlorophenyl)-phenylthiophosphonate
0,0-diethyl-0-(4-me~hylmercapto-3,5-dimethylphenyl)-thiophos-
, phate
.. . .. .
4,4'-bis-(0~0-dime~hylthiophosphoryloxy)-diphenyl disulphide
0,0-di-(B-chloroethyl)-0-(3-chloro-4-methyl-coumarinyl-7)-
.. ,.................................................................... .:
` 15 phosphate
;v S-(l-phthalimidoethyl)-O,O-diethyldithiophosphate
~- 0,0-dimethyl-0-(3-chloro-4-diethylsulphamylphenyl)-thiophosphate
O-methyl-0-(2-carbisopropoxyphenyl)-amidothiophosphate
5-(0,0-dimethylphosphoryl)-6-chloro-bicyclo(3 2,0)-heptadiene(1,5)
0-methyl-0-(2-i-propoxycarbonyl-1-methylvinyl)-ethylamido-
thiophosphate. ~ -
Nitro~henols and derivatives
.. . .
.
4,6-dinitro-6-methylphenol, sodium salt [Dinitrocresol]
dinitrobutylphenol-(2,2',2")-triethanolamine salt
2-cyclohexyl-4,6-dinitrophenyl ~Dinex~
,. , '
. . .
- 12 -
.
. , ................. , . . : .. ~
- - 1047489
,,'
. .
2-1-methylhep~yl)-4,6--dinitrophenyl-cro~onate [~i.nocap]
2-sec.buty]--4,6-dinitrophenyl-3-mle~hyl butenoate ~inapacryl3
2-sec,b~ltyl-4,6-dini.trophenyl-cycloprop~.onate
2~sec.butyl-4$6-dinitrophenylisopropylca-rbonate [~inobuton]
, 5 ~liscellaneous
f,~ pyrethrin::I
s pyreth-rin II
3-allyl-2 methyl-4-oxo-2-cyclopcntan-1--yl-chrysanthemumate
(A l le tllrin)
6-chloropiperonyl-chrysanthemuma~e (Bartllrin)
~ 2,4-dimethylbenzyl-chrysanthemumate (Dimethrin)
,, 2,3,4,5-tetrahydrophthalimidome'l:hylcllrysanthemumate
4-chlorobenzyl-4-chlorophenylsulphide [Chlorobensid]
- ~
r, ' 6-methyl-2-oxo-1,3-dithiolo-[4,5-b]-quinoxaline (Quino- -
~: 15 methi.onate~ -
'!: (I)-3~(2-furfuryl)-2-methyl-4-oxocyclopent-2-enyl(I)-(cis-~
trans)-chrysanthemum-monocarboxylate ~Furethrin3
2-pivaloyl-inclane-1,3 dione [Pindon]
4-chlorobenzyl-4-fluorophenyl-sulphide [Fluorobenside]
5,6-dichloro-1-phenoxycarbamyl-2-trifluoromethyl-benzimidazole
[Fenozaflor]
p-chlorophenyl-p-chlorobenzenesulphonate [Ovex]
p-chlorophenyl-benzenesulphonate [Fenson]
- 13 -
~047489
p-chlorop'lenyl-2,4,5 trich].orophenyl.st~ 0ne [Tcl:radi:Eon~
p- clllorophenyl-2,4,5-trichlo~o~ ylsull)hj-.1e ~JTel~rasul~
p - ch] oroben~l p - chlorophenyl sulphicle [ Ch:l orobens i de ]
2 - thio ~l , 3--dithiolo- (5, 6) -qulnoxaline [Thiochinox ]
prop-2-ynyl-(4-t-butylphenoxy)-cyclohe~ylsulphite [Propargil].
l~ormam;.dines ~,
, . _ .
l-dimechyl-2- (2 ' -met:hyl-4' -chlorophenyl) -formamidine
(CELC~ODIM~
l-metl-yl-2-(2' methyl-4~-chlorophenyl)-~ormc.midi.ne
1-methyl-2- (2 ' -methyl-4' -bromophenyl) -~ormamidine
l-methyl-2 - (2 ', 4 ' -dime thylphenyl ) - formamidine
l-n-butyl-l-methyl-2- (2 ' -me~hyl -4' -chloro~henyl) -Eormamidine
l~methyl-l- (2 ' -methyl-4' -chloroaniline-met:llylene)-~ormarnidi.ne
2- (2"-methyl-4"-chlorophenyl-formamidine :~
l-n butyl-2- (2 ' -methyl-4' -chlorophenyl-imino) -pyrolidine
Urea
N-2-methyl-4-chlorophenyl-N' ,N' -dimethyl-thiourea
Carbamates
l~naphthyl-N-methylcarbamate (CARBARYL) .: .
2--butinyl-4-chlorophenylcarbamate
4-dimethylamino-3,5-xylyl-N-methylcarbarllate
- 4-dimethylamino-3-tolyl-N-methylcarbamate (AMINOCARB)
4-methylthio-3,5-xylyl-N-methylcarbamat:e (ME:T~IIOCAP~B)
3,4,5-trimethylphenyl-N-methylcarbamate
2-chlorophenyl-N-methylcarbamate (CPMC)
. , , , . ' ' ' ,
- 14 -
.' '
" .
:; ~
~047
~; 5 cllloro-G-o;o~2-no~borarle carbonitrile~O~ etllylcarbamoyl)~
~ -,, .
. oxime
,", 1-(dime~ $~1c~ba}noyl-5~me~1lyl 3-pyra~:olyl~N,N-dimetllylcarba
mate (DI~ETILA~l)
2,3-dihydro-2,2-dimethyl-7-benzofuLanyl-N-metllylcarbamate
, (CARBOFUR~N)
,,.', 2-methyl-2-me~hylthio-propionaldehyde-0-(metllylcarbamoyl)-
ox:Lme (ALDICARB)
;~: 8-quinaldyl-N-methylcarbamate and its salts.
methyl-2-isopropyl-4-(methylcarbamoyloxy)carbanilate
m-(l-ethylpropyl)phenyl-N-methylcarbamate
3,5-di-tert.butyl--N-methylcarbamate
m-(l methylbutyl)pllenyl-N-methylcarbamate
2~isopropylphenyl-N-methylcarbamate
;. 15 2-sec.butylphenyl-N-methylc2rbamate
:, ~ m-tolyl-N- methylcarbamate , -
2,3-xylyl-N-methylcarbamate
3-isopropylphenyl-N-methylcarbamate
3-tert.butylphenyl-N-methylcarbamate
. 20 3-sec.butylphenyl-N-methylcarbamate
; . 3-isopropyl-5-methylphenyl-N-methylcarbamate (PRO~EC~RB)
3,5-diisopropylphenyl-N-methylcarbamate
- 2-chloro-5-isopropylphenyl-N-methylcarbama~e
2-chloro-4,5-dimethylphenyl-N-methylcarbamate
2-(1,3-dioxolan-2-yl)phenyl-N-methylcarbamate (DIOXACARB)
- 15 -
~` ~047~89
:
,S-dir.letl~ .-1,3-dioxolan-2-yl)-pllenyl~ net:hylcarbamate
2-(1,3-dioi~olan~~-yl)pllenyl-N,~I-dimetllylc~rbam~te
2-(1,3-di ~.hiolan-2-yl) N,N-di.methylcarbamat:e
2-(1,3-dith;olan-2-yl)phenyl-N,N-clim~tllylcarlamate ,
- 5 2-isopropoxyphenyl-N-me~hylcarbamate (APROC~B)
2-(2-prop;nyloxy)phenyl-N-methylcarbarnate
3-(2--propinyloxy)phenyl-N-me,llylcarbamate
2-dimetllylaminophenyl-N-methy:lcarbamate -~
2-diallylaminophenyl-N-met:hylcarbamate
~-~-di.allylamino-3,5-xylyl-N-methylcar~am2te (ALL~'XICARB)
4-benæothienyl-N-methylcarbamate
2,3-dihydro--2-me~llyl-7-ben~o~uranyl-N--methy].carbamate
: 3-methyl-1-phenylpyrazol-5-yl-N,N-di.methylcarbamate
l-isopropyl-3-methylpyrazol-~-yl-N,N dimethylcarl~amate (ISO~N)
2-dimethylclmino-5,6-dimethylpyrimidin-4-yl-N,N-dimethyl-
carbamate3-methyl~-dimethylaminomethyleneiminophenyl N-methyl-
carbamate
3,4-dimethylphenyl-N-methylcarbamate
2-cyclopentylphe~-N-methylcarbamate
3-dimethylamino-metllyleneiminophenyl-N-methylcarbamate
(FO~METANATE) and its salts ~ :
l-methylthio-ethylimino-N-methylcarbamate (METHOMYL)
2-methylcarbamoyloximino-1,3-dithiolane .~ -
5-methyl-2-methylcarbamoyloximino-1,3-oxythiolane
- 16 -
' ~
' ~0474ss
2 (1-me~hoxy-2 propo,~y)ph~nyl~ -tne~hylcarbaMate
2~ utin-3-yl-o~)phenyl-N-~l~e~llylca~l~aMa~e
:1. c1i.metl~yl.carbamyl-l-me~ y].t:llio-O-me~h,71carhalrlyl-formoxime
1-(2~-cyanoethylthio)-0-methylcarbamyl-acetaldo~f.lme
]-methylthio-0-carbamyl~acetalcloxime
0-(3-sec.butylphenyl)-N-pllenyltllio~N-methylcarballJate
2,5-dime~hyl-1,3~dithiolane-2-(0 methylcarbarnyl)-aldoxime)
0-2-diphenyl-2~-metllylcarbamate
~` 2-(~-methylcarbamyl-oximino)~3-chloro-bicyc~o[2.2,1]lleptane
2-(N-me~hylcarbamyl-oximino)-bicyclo[2.2,1]heptane
3-isopropylphenyl-N-methyl-N-cllloroacetal-carbamate
3-isopropylphenyl-N-mcthyl-~-methy].thiome~hyl-ca-rbamate '~
.~ 0-(2,2-dimethyl-4-chloro-2,3-dihydro-7-benzofuranyl)-N-methyl-
. .
carbamate
0-(2,2,4-trimethyl-2,3-dihydro-7-benzofuranyl)-N-methylcarba-
rnate
0-naphthyl-N-methyl-N-acetal-carbamate
0-5,6,7,~-tetrahydronaphthyl-N-methyl-carbamate
3-isopropyl-4-methylthio-phenyl-N-methylcarbamate
3,5-dimethyl~4-methoxy-phenyl-~-methylcarbamate
3-methoxymethoxy-phenyl-N-metllylcal-bamate
3-allyloxyphenyl-N-methylcarbamate
2-propargyloxymethoxy-phenyl-N-methyl-carbamate
2-allyloxyphenyl-N-methyl-carbamate
4-methoxycarbonylamino-3-isopropylphenyl-N-methyl-carbamate
- 17 -
- 1047489
3,5-d;rn~l Hy~ metl~c)x~Jcarbollylamino-pheny-l-N-methyl-carbama~e
~-y-me~l-y~ iol~o~y~ eny]~ nethyl- ca~ a~ -
3-(a-netlloxym~thyl-2-propeilyl)-phenyl~N-methyl-carbamate
2 chloro-5-tert.-butyl-phcny]-N-metllyl-carbamate
4~(methyl-propargylamino 3,5-xyly].~N--methyl-carbamate
4-(methyl-y-cl-lloroallylalllino)-3,5-~ylyl-N--met:hyl-carbamate
4-(methy]-~-chloroallylamino)-3,5-xylyl-N-methyl-ca]^bamate
l-(~-ethoYyca~:bonylethyl) 3-methyl-5-pyrazolyl-N,N-dimethyl-
carbamate
; 10 3- methyl-4 (dimethylamino-methylmercapto-methyleneimino)-
phenyl-N methyl-carbamate
1,3-bis(carbamoylthio)-2-(N,N-dimethylamino)-propanehydro-
:,
chloride
5,5-dimethylhydroresorcinoldimethylcarbamate
2-[ethyl-propargylamino]-phenyl.-N-methylcarbamate
.` 2-[methyl-propargylamino]-phenyl-N-methylcarbamate
~ 4-[dipropargylamino]-3-tolyl-N-methylcarbama~e
'< 4-[dipropargylamino]-3,5-xylyl-N-methylcarbamal:e ~ '.
! 2-~allyl-isopropylamino]-phenyl-N-methylcarbamate
3-[allyl-isopropylamino]-phenyl-N-methylcarbamate
; Chlorinated Hydrocarbons
y-hexachlorocyclohexane [GAMMEXANE; LINDAN; y HCH]
~.,
1,2,4,5,6,7,8,8-octachloro-3a,4,7,7a -tetrahydro-4,7-
- methylene indane ~CHLORDAN]
1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-
.
- 18 -
. . .
,
1047489
methylene indane
1,2,3,4,10,10-hexachloro-1,4,4~,5,8,8~-hexahydro-endo-1,4-exo-5,8-dimethano-
naphthalene
1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-exo-1,4-
endo-5,8-dimethanonaphthalene
1,2,3,4,10,10-hexachloro-5,7-epoxy-1,4,4~,5,6,7,8,8~-octahydro-endo-endo-
5,8-dimethanonaphthalene.
: The compounds of the formula I are also suitable for combatting
plant pathogenic nematodes.
: 10 The compounds of the formula I may be used as pure active sub-
stance or together with suitable carriers and/or additives. Suitable
- carriers and additives can be solid or liquid and correspond to the sub-
stances conventionally used
,~
;'
.~
,,
h -19-
~0~7489
in formula~ioI2 tccllnique such, fo~ e~ample, as solvcnts,
<lispersclllts, ~e~ g agel-lts, a~lllesives, tllickeners~ binders
and/o-r fcl^tilisers.
For application, the compounds of the forrnula I may
; 5 be processed to dusts, emulsion concentrates, granllles, dis~
persions, sprays, to solu~ions, or suspensions, in the con-
- ventiona] form-llation which is co~nonly en-ployed in app]i
cation technology ~lention may al~so be made o~ cattle dips
and spray races, in which aqueous preparations are used.
-~ 10 The agents according to the invention àre manuac-
tùred in lcnown manner by intimately mixing and/or grinding
active sul~stances of the for~ula I with the suitable carriers,
optionally with the addition of dispersants or solvents
WlliCIl are inert towards the active substances. The active
subs~ances may take, and be used in, the following forms:
Solid forms:
Dusts, tracking agents, granules, coa~ed granules,
impre~nated granules and homogeneous granules.
Liquid forms: i
a) active substances which are dispersible in water:
wettable powders, pasts, emulsions; ~ ;
b) solutions.
To manufacture solid forms (dusts, tracking agents),
the active substances are mixed with solid carriers. Suit-
able carriers are, for example: kaolin, talcum, bolus, loess,
, . . .
- 20 -
~)47489
chalk, limes~one, ground limes~olle, a~ac]ay, dolomite, ;-
diatomacec)us ea-rth, precipita~cd silica, alkaline earth
sili.cates, sodium and potassium alumin:ium silica~e~s (feld-
spar and mica), calcium~d inagnesium su]phates, magnesium
: 5 o~ide, ground synthetic materials, fertilisers, ~or example
`-- ammonium sulphate, ammonium phosphate, ammonium ni~rate,
: urea, ground vegetable products, such as corn meal, bark
.:
dust, sawdust~ nutshell meal, cellulose powcler, residues o
plant extract:ions, activated charcoal etc These substances
can either be used singly or in admixture ~ith one another.
:- Granules can be very eas:lly manufactured by dissol-
ving an active substance of the formula I in an o~ganic
solvent and applying the resul~ing solution to a granulated
material, for example attapulgi~e, SI02, granicalcium,
belltonite etc and then evaporating the solvent.
Polymer granules can also be manuf~c~ured by mixin;,
; the active substances of the formula I with pol~erisable
compounds (urea/formaldehyde; dicyandi2mide/formaldehyde;
melami.ne/formaldehyde or others), whereupon a mild polyn~eri-
sation is carried out that does not affect the active
substances and in the process of which the granulation is
carried out during the gel formation It is more advantageous
to impregnate finished, porous polymer granules (urea/
formaldehyde, polyacrylonitrile, polyester or others) ~Jhich
have a specifi.c surface area and a favourable predeterminablF:
n47~8
: " '
- adsorption/desorption ratio, with the ac~ive substances, ~or
example in th~ orm of th~ir solutions (in a lo~ boiling
solvent) and to remove ~he solvent. Polymer granules of this
kind in the ~o~m of microgranules having a bulk density of
~, ....
- 5 300 g/liter to 600 g/liter can also be manu~actured ~ith the
aid of atomisers. The dusting can be carried out from aircrat .~ :
over extensive areas of cultures of useful plants.
. . It is also possible to obtain granules by compacting ~ .
.. the carrier ~ith the active substan.ce and carriers and subsc-
- 10 quently com~linu~ing the product.
To tllese mixtures can also be a.dded additives which
;. stabi.lise the active substance and/or non-ionic, anioni.c arld
~., .
. cationic sur~ace active substances, whicll, for example,
improve the adhesion of the active ingredients on plants or
parts o plants (adhesives and agglutinants) and/or ensure a
better wettability (wetting agents) and dispersibility
(dispersirg agents). Examples of suitable adhesives are the
following: olein/chalk mixture, cellulose derivatives (methyl ::
cellulose, carboxymethyl cellulose), hydroxyethyl g]ycol - .
: 20 . ethers o monoalkyl and diallcyl phenols having 5 to 15
ethylene ox;de radicals per molecule and 8 to 9 carbon atoms
; in the alkyl radical, lignin sulphonic acids, their alkali
metal and alkaline earth metal salts, polyethylene glycol
ethers (carbowaxes), ~atty alcohol polyethylene glycol ethe~s
having 5 to 20 ethylene oxide radicals per molecule and 8 to
. .
- 22 -
.. . .. .. .. .. .. ..
ln47489
. .
18 carbon atoms in thc atty a]cohol moiety, condensation
produc~s o~ e~hylene oxide/propylcne oY~ide, polyvinyl pyrro-
lidones, polyvinyl alcohols, con~ensation products of urea
and ormaldehyde, and also late~ products.
The ~ater-dispersible concentratcs of the active
substance, i.e. ~ettable po~ders, pastes and emulsiiable
concentra~es, are agents whicll can be diluted wi~l-l water to
. . ,
~ any concentra~ion desirecl. They consist of active substance,
.... .
~ carrier, opti~nally additives which stabilise the active
- 10 substance, sur~ace-active sùbstance and anti-foam agents
; and, optionally,solvents.
. .
l~ettable powders and pastes are ob~ained by ml~ g
and grinding the active substances with dispersing agents and
~ulverulent c~rriers in suitable apparat-us un~il homogeneity
is attained. Suitable carriers are, for exam.ple, those men-
tioned for the solid forms of application. In some cases it
is advantageous to use mixtures of dif~erent carriers. As
dispersing agents there can be used, for example, condensation
products o~ sulphonated naphthalene and sulphonated naphtha
lene derivatives with formaldehyde, condensation products o~
naphthalene or naphthalene sulphonic acids with phenol and
formaldellyde, as well as-alkali, ammonium and alkaline earth
me~al salts of lignin sulphonic acid, in addition, allcylaryl
~ sulphonates, alkali and alkaline earth metal salts o~ dibutyl
: 25 naphthalene sulphonic acid, fatty alcohol sulphates such as
- 23 -
.~,, , ,,, ,, ,., ,. , . , ., _
.
' ~
-` ~0474t39 ~:
salts of sulpllated hexadecanols, heptadecanols, octadecanols,
and salts o suli~ha~ed ~atty alcol~ol glyco] e~hers, the
sodiurll salt o~ oleoyl e~hionate, t}-le soclium salts o oleoyl
methyl taurid~, ditertiary acetylene glyco]s, dialkyl di-
~`~ 5 lauryl a~nonium chloride and fa~ty acid alkali and alkaline
earth metal salts.
Suitable anti-fo~m agents are silicones.
The active substances are mixed~ gro~md, sieved and
strained ~ith the additives cited hereinabove, in such a
manner that, the size of the solid particles does not exceed
0 02 to 0,04~in wettable po~ders, and 0.03~ in past-es.
i To produce emulsifiable concentrat~es and pastes, dispersing
.~ agents such as those cited above, organic solvents, and water
are used. Examples of suitable solvents are: a]cohols, benzene,
xylene, toluene, dimethyl sulphoxide, and mineral oil fractions
which boil between 120 and 350C. The solvents must be ~
pract-ically odour]ess, not phytotoxic, and inert to the active -
substances.
Furthermore, the agents accor~ing to the invention
20 can be applied in the form of solutions. For this purpose -~
: . :
v the active substances, or several ac~ive substances of the `
general ormulà X, are dissolved in sui~ab]e organic solvents,
mixtures of solvents or in water Aliphatic and aromatic h~r~ ~-
drocarbons, chlorinated derivatives thereof, alkyl naphthalene~
25 and mineral oils, singly or in admixture wi~h each other, can
,... .
J
- 24 -
.
'
" .. .... ... . .... .... .... . ... .. . .. . . . . .
, . . .
. .
`;~ 1(~4~ 9
.. ~ .
43.~ parts of xylene.
~- b) 25 parts of active s~lbstance,
;- 2 5 parts of epoxidised vegetable oil,
parts of an alkyl.arylsulphonate/fatty alcohol--
polyglycol ether m:i~ture,
. 5 parts o dimethylforrllamide,
. 57.5 parts of xylene.
~` . From ~hese concentra~es i~ is possible to pro~lce,
by dilution ~.7:ith ~.7ater, emulsions o any desired concentra
tion.
- Spray:
The ~ollowing constituents are used to prepare a
5% spray:
: 5 parts of active subs~:ance,
.. 15 1 part of epichlorohydrin,
94 parts of benzine (boiling limits 160~ - 190C).
~ ' ~
,, .
., ' , ~
,,
''"
'~ ' .
. .
- ~ , .
,
1.7 parts of Chami~agn~ chalk/hydroxyethyl cellulose
: mi~ture (1:1),
~-
J '~ ~. 3 parts of sodium aluminium silicate,
lG.5 parts of kieselguhr,
46 parts of kaolin
d)10 parts o active substance,
3 par~s of a mix~ure of the sodium salts of
:~ saturated fatty alcohol sulphates,
: ..... .
~:: 5 parts of naphthalenesulpllonlc acid/~ormaldehyde
~ "
condensate,
82 parts o kaolin.
- ~ The active substances are intimately mixed, in suit-
able Ir~ixers, with the additives, the mixture being then ground
~;.: ~ - .
, in tlle appropriat-e mills and rollers. Wettable po~ders are
:: 15 ob~ai.ned which can be diluted ~7ith ~Jater to give suspensions
... .
- of any desired concentration.
.~. .
~;' mul ial~ e concentrates:
i.l .
.. The ollo~ing substances are used to produce a) a
10% and b) a 25% emulsifiable concentrate:
a) 10 parts o active subs~ance,
A l3.4 parts of epoxidised vegetable oil~
13.4 parts of a combination emulsifier consisting
- of fatty alcohol polyglycol e~her and alkyl-
arylsulphonate calcium salt,
" .
s 25 bO parts of dimethylformamide,
,,"
- 26 _
.. .. . ... . ..... ... ... ... ... . ....... . . ... . .... .. .. .... . .. ... . .. . ....... . .. . .. .. . . . . ..
,; . . - : ~ . - .,
, ' ' ''. ~
9~89
3 . SO parts of polyethylelle glycol,
91 par~s of l~aoliII (particle size 0.3 - 0.8 mm).
The active substance is mixed witll epichlorohydrin
: and dissolved wltll 6 parts of ace~olle; the polyethy]ene .
glycol alld cetyl polyglycol ethex are then adcled. The th~s
~:. o~tai.ned solution is sprayed on kaolin, and the ace~one
- subsequellt].y e~raporated in vacuo.
I~ettable pow~er:
Th~ following constituen~s are used for the pre-
10 paration of a) a 40%, b) and c) a 25%, and d) a 10% wettable
T~Wder:
.~ a)40 par~s of active substance,
,
parts o sodium lignin sulphonate,
1 part of sodium dibu-~yl-naph~halene sulphonate,
54 par~s of silicic acid,
.. ~ b) 25 parts of active substance,
4.5 parts of calcium lignin sulphona~e,
1.9 parts o Champagne chalk/hydroxyethyl cellulose
. mixtuxe (1:1),
1.5 parts of sodium dibutyl naphthalene sulphonate,
. . ~ .
. 19,5 parts of silicic acid,
19,5 parts of Champagne chalk,
28,1 parts of kaolin.
c)25 paxts of active substance,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
,, , :
. . .
_ 27 -
.
~ ' ~
- - 1047489
be used as organic solvents.
The content of active substallce in the above des-
cribed agents is be~een 0. l~/o to 95%, in wllicll connection it
should be ment.ioned that, in the case of application from ~-
aircra~ or soMe other suitable means of application, it is
possible to use concen~rations of up ~o 99.5% or even pure
ac~ive substance. -
The active substances o the fonllula I can, for
example, be formulated as follows:
~ .
~ 10 Dusts
:
The follo~Jing substances are used to manufacture a)
~ a 5% and b) a 2% dusc:
a)5 parts o active substance
95 parts of talcum
- 15 b)2 parcs of active substance
, 1 part of highly disperse silicic acid
c 97 parts of talcum.
The active substances are mixed with the carriers
and ground.
~,; 20 Granules
;~ The following substances are used to produce 5%
,ji granules:
- 5 parts of active substance,
0,25 parts of epichlorohydrin,
- 25 0 25 parts of cetyl polyglyco] eLher~
.
, :
- 28 -
. ,.,.. ,,.. ,., . ,,.. ,.,.. . ,,.. ,, ,., .,. , . .. ,, .. , ~ .
~047489
- Example 1
: ~ S
At room temperature 10.1 g of 0-ethyl-~-(n)-propyl-thio~-
~phosphoric chloride in 2~ ml of absolute ether are added
dropwise to a solution of 11.6 g of 4-hydroxy-4'-chloro-azo
benzene and 5.1 g of triethylamine in 150 ml of absolute ether.
The salt precipitate is filtered off and the mixture is treated
with 200 ml of ice water with stirring. The organic phase is
isolated, washed once with water and shaken twice with ice-cold
"
~ 5% sodium hydroxide solution and then washed neutral with
,. .
. water. The ethereal phase is then treated with activated char-
coalJ filtered, dried, and the solvent is evaporated. The resi-
r: i
, due is dried for 3 hours at 70C and 0.1 Torr to give the com-
~; pound of the formula
,;
.. , O
` C1~3N=N~3 ~S) C ~I ( n )
3 7
, ................................................ . .
r~,' with a refractive index of n20 1.6185.
The following compounds are also manufacture in analogous manner:
, . . . .
.
: ~N=~o-~a3~l7(n~ nD20= 1,6142 ` ~
ri~ ~ O .. ' : .
-- ~==~ ~==\ 11 /OC2H
,- Cl ~ N=N ~ ~SC3H7(n) D - 1,6251
''` ' ' .
, ~ .
-
~
:.
. :
- 1047~39
`. S
Cl~N=I~-~ 11 <3CzH5 nD20
SC3H7(n) = 1,6345
. C 1
,. I , O .::
C1~3N--N~ C3H7(n) nD20 _ 1, 6300
,. o
" CH3~~ `~ 3 7 ( ) nD2 = 1, 6132 :
C1~3-N=N~~,<OC E5 nD - 1, 6495
'i Cl S
~=~ ~c=~11 /OC H
~ ~ ~N=N~ 3 7 ( nD ~ 1, 6348
;:' S
i~, CH~ ~N~3 3 7 ( ) n20 = 1, 6336
..
~' O
11 ~OC H
~,~ ~N--N~o--P< 2 5 CH n2o
., - SCH2--CH< 3 D - 1, 6082
0~I3
Cl~3N-N~ ~<OC2H5 20
SCH2--CH<~3 nD = 1, 6078
~" .
: . '
~, ~
- 30 -
. , .
Example 2 1047~89
~,, ' .
~ction against ticks
.
~ A) Rhipicephalus bursa
, . .
Five adult ticks and 50 tick larvae were counted into
a glass tube and immersed for 1 to 2 minutes in 2 ml of an
aqueous emulsion from an emulsion series each containing 100,
; 10, 1 and 0.1 ppm f test substance The tube was then sealed
~ . .
with a standardised cotton wool plug and placed on its head,
so that the active substance emulsion could be adsorbed by
the cotton wo~l.
. In the case of the adults evaluation took place after
2 weeks, and ;n that of the larvae after 2 days. Each test
was repeated twice.
:
'~ B) Boophilus microplus (larvae)
~, .
; Tests were carried out in each case with 20 OP-sensitive
,, larvae using an analogous dilution series as in the case of ~;
;:~ test A. (The resistence refers to the tolerability of Diazinon).
,~ :
' The compounds according to Example 1 acted in these
- tests against adults and larvae of Rhipicephalus bursa sensi-
tive and OP-resistent larvae of Boophilus microplus.
Example 3
Action against Chilo suppresalis
.
Six rice plants at a time of the variety Caloro' were
transplanted into plastic pots (diameter at the top = 17 cm)
and reared to a height of about 60 cm. Infestation with Chilo
~ 31 _
: :
-- - " 1047~39
, . ,
` suppressalis lar~ae (Ll: 3-4 mm long) took place 2 days after
the active substance had been applied in granule form to the
paddy water (rate of application: 8 kg of active substance
per hectare). Evaluation of the insecticidal action took place
10 days after application of the granules.
. .
. The compounds according to Example 1 were active in the
~- above test against Chilo suppressalis.
. .
Example 4
,.
~ Action against soil insects
!,:
,`",'~ .
Sterilised compost earth was homogenously mixed with a
`~ wettable powder containing 25% of active substance so that
there resulted a rate of application of 8 kg of active sub-
stance per hectare.
Young zucchetti plants (Cucumis pepo) were put into plastic
.::
pots with the treated soil (3 plants per pot; diameter of pot
~; = 7 cm). Each pot was infected immediately afterwards with 5
".
; Aulacophora femoralis and Pachmoda or Chortophila larvae. The
~; control was carried out 4, 8, 16 and 32 days after depositing~,~ the larvae.
' At 80-100% kill after the first control, a fresh infesta-tion with 5 larvae each was carried out in the same soil sample
with 3 new zucchetti plants. If the activity was less than
` 80%, the remaining larvae remained in the soil sample until
the control immediately following . If an active substance at
a rate of application of 8 kg/ha still effected a 100% kill,
- 32 -
~ ` `
~ . --
~047~89
~:; a further control with 4 and 2 kg of active substance per
hectare was carried out.
.
In the above test, the compounds according to Example 1
displayed action against Aulacophora fermoralis, Pachmoda and
; Chortophila larvae.
~ Example S
- Acaricidal action
` Phaseolus vulgaris (dwarf beans) have an infested piece
of leaf from a mass culture of Tetranychus urticae placed on
" ,
them 12 hours before the test for the acaricidal action. The
mobile stages which have migrated are sprayed with the emul-
sified test preparations from a chromatography atomiser so
that the spray broth does not run off. The number of living
s and dead larvae, adults and eggs are evaluated after 2 to 7 -
days under a stereoscopic microscope. During the "interim", the
.; treated plants are kept in greenhouse compartments at 25C.
The compounds according to Example 1 were active in the
.: .
above test against eggs, larvae and adults of Tetranychus -
. . .
urticae.
Example 6
Action a~ainst soil nematodes
To test the action against soil nematodes, the active
substance is
.
r :' ,
- 33 -
' ~ ln47~ss
applied to and intimately mixed with soil infected with root
j; .
'~ gall nematodes (Meloidgyne Arenaria), Immediately afterwards,
' tomato cuttings are planted in the thus prepared soil in a
series of tests and after a waiting time of 8 days tomato
, seeds are sown in another test series.
In order to assess the nematocidal action, the galls
present on the roots are counted 28 days after planting and
sowing respectively. In this test the compounds according to
Example 1 display good action against Meloidgyne Arenaria.
.:
~'. .
, .
t..
r.;
~ :
,~' ,'.
:,.';~;
~5'~ .
,~,,
~''' '
.. , -- . . . .
. ~ .
,
,'. ~ ~ .
~, ~'' .
~. .
.,:
': :
' .
- 34 -
,...
i'
, -
, ..
~ ~ .
