New esters of acids N (thio) carbamyl arena (thio) carboximidic, proceeded to prepare them, produced insecticidal which contain some, and their application to the fight against the depredaters.

20-11-1986 дата публикации
Номер:
OA0000007821A
Автор:
Принадлежит: Hoechst Ag
Контакты:
Номер заявки: 58-00-1984397
Дата заявки: 21-09-1984

[1]

The present invention concerns novel esters of n-carbamoyl - (alkylthio) - arene (thiourea) carboximidiques, processes for their preparation, insecticides containing them, and their use for combating pests.

[2]

It is known that certain esters d'acidæN-carbamoyl-benzene thioether-anomer 2.6 ^) carboximidiques exhibit insecticidal (European Patent 5944). These compounds have however drawbacks from the stage of their application, in particular deficiencies in material efficiencies.

[3]

This being, the present inventors have found novel esters of n-carbamoyl - (alkylthio) - arene (thiourea) carboximidiques which exhibit valuable insecticidal properties.

[4]

The present invention is therefore directed to compounds of formula I:

[5]

[6]

Rthe X to R,, each represent, independently of each other:

[7]

hydrogen; alkyl in the Cj GC-, the Cj GC-alkoxy, a alkylthioT c ^ - GC, GC ^ C alkylsulfinyl, alkylsulfonyl C ^ GC or alkylsulfonyloxy C. ^ - GC, the radicals just mentioned can carry as substituent (e) one or more halogen;

[8]

halogen or nitro radical,

[9]

to RJ450 are each, independently of one another:

[10]

hydrogen; C alkyl ^ - GC, GC ^ c-alkoxy, alkenyloxy C ^ GC, alkyl thiol in the Cj-to-atrial, alkenylthio c ^ GC, alkylsulfonyl or hydroxyalkyl the Cj GC-c ^, the radicals just mentioned can carry as substituent (e) one or more halogen; halogen; a nr.ixo; benzyloxy optionally bearing a halogen, a halogeno alkyl C,-C.C. T- a halo-alkoxy in cV. - C.C. , a cyano or nitro; a alcoxycarbonylë which alkoxy contains from 1 to 9 carbon atoms; a radical NRR 'wherein R and R' are each, independently of one another, C alkyl ^ - GC, a alcënyle c ^ - GC, alkynyl GC-GC(these substituents can also carry one or more halogen atoms), a halogen, nitro or cyano, or R and R 'together form and with 1' common nitrogen atom a saturated or six-membered ring which may contain, as link of its cycle, an oxygen or sulfur atom or a radical. An NR "(the symbol R" is an alkyl C - ^ - GC) and which may have a C alkyl ^ - ^ R-GC and RG can further form together a radical alkylene-dioxyethylene containing one or two carbon atoms and optionally bearing a halogen or a radical CFg,

[11]

X represents a radical gold ^ ^ wherein R denotes an alkyl in GC-GC optionally halogënë, cycloalkyl GC or GC, GC-GC in a alcënyle, alkynyl GC-GC or benzyl optionally halogenated, or X represents a radical SRjg ^years wherein R ^2 c alkyl denotes - ^ - GC or benzyl, each of these radicals can carry as substituent (e) one or more halogen, and

[12]

Y represents oxygen or sulfur,

[13]

with the proviso that, when R ^ and RG each represent fluorine and R2 , r.3 and R4 each represent hydrogen, none of the rg radicals to R1Q c alkyl or a ^ - GC halogenated or halogen.

[14]

Is given below, as examples, a list of compounds of formula I according to the invention:

[15]

N-NC - (fluoro 2 phenyl) - carbomoyl] difluoro 2.6 benzêne-to-carboximidate D.1 ethyl

[16]

N-n-[ - (fluoro 2 phenyl) - carbomoyl] dimethoxy-2.6 ethyl benzene-carboximidate

[17]

N-n-[ - (ëthoxy-to-2 phenyl) - carbomoyl] fluoro 2 - carboximidate ethyl benzene

[18]

N-NC - ((tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -3) --carbamoyl] ethyl benzene-carboximidate

[19]

N-n-[ - (nitro 3 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[20]

N-n-[ - (nitro 3 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[21]

N - [the n - ((trifluoromêthyl-to-1 trifluoromethyl 2, 2, 2 êthylramino) -3 phenyl) - carbomoyl] fluoro-a 2 ethyl benzene-carboximidate

[22]

N-n-[ - (mêthoxycarbonyl-to-3 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[23]

N - [D - (difluoiomëthyl-to-3 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[24]

N-n-[ - (trifluoromêthyl-to-3 phenyl) - carbomoyl] fluoro 2 benzècarboximidate ethyl

[25]

N-NC - (trifluoromêthyl-to-3 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[26]

N - [D - (fluoro 4 phenyl) - carbomoyl] fluoro 2 benzene-carboxmidate ethyl

[27]

N - LTF - (fluoro 4 phenyl) - carbomoyl] chloro 2 fluoro 6 benzene-carboximidate of methyl-1 ethyl

[28]

N - [D - (chlorophenyl 4 phenyl) --carbamoyl] ethyl benzene-carboximidate

[29]

N-n-[ - (chlorophenyl 4 phenyl) - carbomoyl] benzene-carboximidate propargyl

[30]

N-n-[ - (chlorophenyl 4 phenyl) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[31]

N - (n-- (chlorophenyl 4 phenyl) - carbomoyl] chloro 2 fluoro 6 methyl benzene-carboximidate

[32]

N - (- jî (difluoromëthoxy-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[33]

N - n-VBE1 - (difliorométKoxy-to-4 phenyl) - carbomoyl) chloro 2 ethyl benzene-carboximidate

[34]

N-n-[ - (difluoromethoxy-4 phenyl) - difluoro 2.6 carbamoyU ethyl benzene-carboximidate

[35]

N-n-[ - (difluoromêthoxy-to-4 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[36]

N-NC - (difluoromethoxy-4 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[37]

N-n-[ - (difluoromethoxy-4 phenyl) - carbomoyl] chloro 2 fluoro 5 ethyl benzene-carboximidate

[38]

N - [D - (difluoroméfchDxy-to-4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[39]

N-n-[ - (difluoromêthoxy-to-4 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[40]

N-n-[ - (chlorodifluorométhoxy-to-4 phenyl) - carbamoyU fluoro 2 ethyl benzene-carboximidate

[41]

N-n-[ - (chlorodifluoromêthoxy-to-4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[42]

N-NC - (chlorodifluorométhoxy-to-4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[43]

N-n-[ - (chlorodifluorométhpxy-to-4 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[44]

N-n-[ - (chlorodifluoromêthoxy-to-4 phenyl) - carbomoyl] chloro 2 fluoro 5 ethyl benzene-carboximidate

[45]

N-n-[ - (chlorodifluorométhoxy-to-4 phenyl) - carbomoyl] dichloride 2.4 benzëne-to-carboxLmidate ethyl

[46]

N-n-[ - (IFFT luorométhoxy-to-4 phenyl) --carbamoyl] ethyl benzene-carboximidate

[47]

N-n-[ - (trifluoromethoxy-to-4 phenyl) - carbamoyU fluoro 2 methyl benzene-carboximidate

[48]

N-n-[ - (trifluoromêthoxy-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[49]

N - bone - (trifluoromethoxy-to-4 phenyl) - carbomoyl] fluoro 2 benzene-carboximidate propyl~

[50]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] fluoro 2 benzene-carboximidate butyl

[51]

L-§Ν-to-£N - (trifluoromethoxy-to-4 substituted phenyl) - carbomoyl] fluoro 2 hexyl benzene-carboximidate

[52]

N - TM - (substituted phenyl trifluoromêthoxy and 4) - carbomoyl] fluoro 2 benzene-carboximidate cyclohexyl

[53]

N-T-NR - (trifluoromethoxy-to-4 substituted phenyl) - carbomoyl] fluoro 3 ethyl benzene-carboximidate

[54]

N-n-[ - (trifluoromethoxy-to-4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[55]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] chloro 4 ethyl benzene-carboximidate

[56]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] iodo 2 ethyl benzene-carboximidate

[57]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] difluoro 2.4 ethyl benzene-carboximidate

[58]

N-NC - (IFFT luoromëthoxy-to-4 phenyl) - carbomoyl] fluoro-to-2.6 DIFs ethyl benzene-carboximidate

[59]

N-n-[ - (trifluoromëthoxy-to-4 phenyl) - carbomoyl] difluoro 2.6 hexyl benzene-carboximidate

[60]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] chloro 4 fluoro 2 ethyl benzene-carboximidate

[61]

N-NC - (trifluororaéthoxy-to-4 phenyl) - carbomoyl] chloroacetamide 5 fluoro 2 ethyl benzene-carboximidate

[62]

N-NC - (trifluoromëthoxy-to-4 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[63]

N-n-[ - (trifluoromethoxy-to-4 phenyl) 5 - chloro 2 carbamoy fluoroorganic 4 ethyl benzene-carboximidate

[64]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] chloro 2 fluoro 5 ethyl benzene-carboximidate

[65]

N-n-[ - (trifluoromëthoxy-to-4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[66]

N-n-[ - (trifluoromethoxy-to-4 phenyl) - carbomoyl] dichloride 2.5 ethyl benzene-carboximidate

[67]

N-NC - (IFFT luoromëthoxy-to-4 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[68]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] pentafluoro relief pattern zêne-to-carboximidate D.1 ethyl

[69]

N-£n - (trifluoromethoxy-to-4 phênyl) - carbomoyl] chloro 2 mêthoxy-to-6 benzëne-to-carboximidate ethyl

[70]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl) fluoro 2 nitro 5 * d-ethyl benzene-carboximidate

[71]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] chloro 2 nitro 5 ethyl benzene-carboximidate

[72]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbamoylj methane-suifo-to-nyloxy and 2 ethyl benzene-carboximidate

[73]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] benzene-carboximidatedifluoromëthoxy and 2 ethyl

[74]

N - [D - (trifluoromêthoxy-to-4 phenyl) - carbomoyl] trifluoromethoxy-to-4 ethyl benzene-carboximidate

[75]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl} trifluoromé-to-thoxy-to-3 ethyl benzene-carboximidate

[76]

N-NC - (trifluoromethoxy-to-4 phenyl) --carbamoyl] methoxy-2 ethyl benzene-carboximidate

[77]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] (difluoro 1.1 dichloroethylene 2.2F. 2 ethoxy) ethyl benzene-carboximidate -4

[78]

N-NC - (trifluoromëthoxy-to-4 phenyl) - carbomoyl] benzene-carboximidatedifluorométhylthio and 2 ethyl

[79]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] nitro 3 trifluoromêthyl-to-5 ethyl benzene-carboximidate

[80]

N-n-[ - (trifluoromethoxy-to-4 phenyl) - carbomoyl] trifluoromëthylbenzëne-to-carboximidate ethyl 2

[81]

N-NC - (trifluoromethoxy-to-4 phenyl) - carbomoyl] trifluoromëthylbenzëne-to-carboximidate methyl 3

[82]

N-NC - (trifluoromëthoxy-to-4 phenyl) --carbamoyl] methyl-2 ethyl benzene-carboximidate

[83]

N-NC - ((tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] benzene-carboximidate propargyl

[84]

The Ν - ςΝ - ((tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) - carbomoyl] benzëne-to-carboximidate trifluoro-2, 2, 2 ethyl

[85]

N-Q-$ - ((tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[86]

N-NC - ((tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) - carbamoylj

[87]

- chlorophenyl 2 ethyl benzene-carboximidate

[88]

N-n-[ - ((tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[89]

N-n-[ - ((dichloro 2.2 difluoro 1.1 ëthoxy) -4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[90]

N-n-[ - ((dichloro 2.2 difluoro 1.1 ëthoxy} - 4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[91]

N-n-[ - ((dichloro 2.2 difluoro 1.1 ethoxy) phenyl -4) - carbomoyl] difluoro 2.6 ethyl benzene oarboximidate

[92]

N - (n-- ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phënyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[93]

N - [the n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[94]

N - [the n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[95]

N - TRFP - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[96]

N - [the n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 ,propoxy) -4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[97]

N - [the n - ((dichloride 1.2 éthényloxy) -4 phënyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[98]

N - [the n - ((dichloride 1.2 éthényloxy) -4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[99]

N - [the n - ((dichloride 1.2 éthényloxy) -4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[100]

N - (n-- (difluorométhylthio-to-4 phenyl) --carbamoyl] - 2 * a fluoro ethyl benzene-carboximidate

[101]

N - {n-- (difluorométhylthio-to-4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[102]

N - [D - (DIFs luorométhylthio-to-4 phënyl) - carbomoyl] fluoro-to-2.6 DIFs ethyl benzene-carboximidate

[103]

N - [n fchlorodifluorométhylthio-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[104]

N - (n-- (chlorodifluorométhylthio-to-4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[105]

N - (n-- (chlorodifluorométhylthio-to-4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidateJ

[106]

N-n-[ - (chlorodifluorométhylthio-to-4 phenyl) - carbamoil j-platinic 2 fluoro 2 ethyl benzene-carboximidate

[107]

N-Jn at - (chlorodifluorométhylthio-to-4 phenyl) - carbomoyl] chloroacetamide 6 fluoro 6 ethyl benzene-carboximidate

[108]

N - [D - (chlorodifluorométhylthio-to-4 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[109]

N - (n-- (chlorodifluorométhylthio-to-4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[110]

N - n-|-, (IFFT luorométhylthio-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[111]

N-Jn at - (trifluoromethylthio and 4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[112]

N - (n-- (trifluoromethylthio and 4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[113]

N - [D - (trifluoromethylthio and 4 phenyl) - carbomoyl] difluoro 2.4 ethyl benzene-carboximidate

[114]

N - n-|- (trifluoromethylthio and 4 phenyl) - carbomoyl] chloro 4 fluoro 2 ethyl benzene-carboximidate

[115]

N - [D - (trifluoromëthylthio-to-4 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[116]

N - (n-- (trifluoromethylthio and 4 phenyl) - carbomoyl] chloro 2 fluoro 5 ethyl benzene-carboximidate

[117]

N - n-|- (trifluoromethylthio and 4 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidatethe MR

[118]

N - cents ΐ - ((tetrafluoro-I-s * I, 2.2 ethyl thio) phenyl -4) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[119]

N - (n-- ((tetrafluoro-1, 1, 2, 2 ethyl thio) phenyl -4) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[120]

N - iïl - ((tetrafluoro-1.1 * 2, 2 ethyl thio) phenyl -4) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[121]

N - (n-- ((tetrafluoro-1, 1, 2, 2 ,éthyl thio) phenyl -4) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[122]

N-n-[ - ((tetrafluoro-1, 1, 2, 2 ethyl thio) phenyl -4) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[123]

N - lïfl - ((chloro 2 Trif or fluoro-a 1, 1, 2 ethyl thio) phenyl -4) - because bamoyl] fluoro 2 ethyl benzene-carboximidate

[124]

The Ν - [ν - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) - because bamoyljchloro and 2 ethyl benzene-carboximidate

[125]

N -|] the n - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) - benzene-carboximidatecarbamoyljdifluoro-to-2.4 ethyl

[126]

N - [the n - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) - carbomoyl]) chloro 4 fluoro 2 ethyl benzene-carboximidate

[127]

N-Jn at - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) - carbamoil!) chloro 2 fluoro 4 ethyl benzene-carboximidate

[128]

N-Jn at - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) carbomoyl ^ - chlorophenyl 2 fluoro 5 ethyl benzene-carboximidate

[129]

N - {ïj - ((chloro 2 Trif or fluoro-a 1, 1, 2 ethyl thio) phenyl -4) - because a-bamoyljchloro-to-5 fluoro 2 ethyl benzene-carboximidate

[130]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethyl thio) phenyl -4) - dichloride 2.4 carbamoylj ethyl benzene-carboximidate

[131]

N - (it - ((hexaf fluoro-to-1.1 ·, 2, 3, 3, 3-propyl thio) phenyl -4) - carbomoyl]] fluoro 2 ethyl benzene-carboximidate

[132]

N - I-&- ((hexafluoroantimonic 1, 1, 2, 3, 3, 3-propyl thio) phenyl -4) - carbomoyl]) chloro 2 ethyl benzene-carboximidate

[133]

N - [the n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3-propyl thio) phenyl -4) - carbomoyl]) difluoro 2.6 ethyl benzene-carboximidate

[134]

N - jïï - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3-propyl thio) phenyl -4) carbomoyl - j-platinic 2 fluoro 4 ethyl benzene-carboximidate

[135]

N-n-[ - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3-propyl thio) phenyl -4) - carbomoyl]! dichloro 2.4 ethyl benzene-carboximidate

[136]

N - [D - (trifluorométhylsulfony1-to-4 phenyl) - carbomoyl} fluoro 2 ethyl benzene-carboximidate

[137]

N - [D - (trifluorométhylsulfony 1 - 4 phenyl) - carbomoyl]) chloro 2 ethyl benzene-carboximidate

[138]

N - (n-- (trifluoromethylsulfonyl-to-4 phenyl) - carbomoyl] difluoro 2, 6 ethyl benzene-carboximidate

[139]

N - NC - (nitro 4 phenyl) - carbomoyl "] fluoro-a 2 benzêne-to-carboximidate ethyl

[140]

N - a DSI - (nitro 4 phenyl) - carbomoyl] chloro 2 benzêne-to-carboximidate ethyl

[141]

N-[] with n - (nitro 4 phenyl) - carbomoyl] fluoro-to-2.6 DIFs ethyl benzene-carboximidate

[142]

N - (n-- (nitro 4 phênyl) carbamoylj - chlorophenyl 2 fluoro 6 ethyl benzene-carboximidate

[143]

N-n-[ - (nitro 4 phênyl) - dichloride 2.6 carbamoyljbenzênè-to-carboximidate ethyl

[144]

N - {n-- (phênyltrifluoromêthyl and 4) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[145]

N - (n-- (trifluoromethyl-4 phênyl) carbamoylj - chlorophenyl 2 fluoro 6 ethyl benzene-carboximidate

[146]

N-n-[ - (phênyltrifluoromêthyl and 4) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[147]

N - (n-- (trifluoromethyl-1 hydroxy-L-trifluoromethyl 2, 2, 2 ethyl) -4 phênyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[148]

N-jjN - (trifluoromethyl-1 hydroxy-L-trifluoromethyl 2, 2, 2 ethyl) -4 phênyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[149]

N - {n-- (trifluoromethyl-1 hydroxy .l trifluoromethyl 2, 2, 2 ethyl) -4 phênyl) - carbomoyl] chloro 2 fluoiîo-to-6 ethyl benzene-carboximidate

[150]

N - (n-- (trifluoromethyl-1 hydroxy-L-trifluoromethyl 2, 2, 2 ethyl) -4 phênyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[151]

N - [D - (trifluoromethyl-1 hydroxy-L-trifluoromethyl 2, 2, 2 ëthyl) -4 phênyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[152]

N-n-[ - (trifluoromêthyl-to-1 hydroxy-L-trifluoromethyl 2, 2, 2 éthvl) -4 phênyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene carboxmidate

[153]

N - [D - (methoxycarbonyl-4 phênyl) - carbamoylj fluoro 2 ethyl benzene-carboximidate

[154]

N - [D - (ethyl-2 phênyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[155]

N-n-[ - ((dimethyl-1.1 ethyl) -4 phênyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[156]

N - [D - (chlorophenyl 4 phênyl) - thiocarbamoyl group] fluoro 2 ethyl benzene-carboximidate

[157]

N - (n-- (trifluoromethoxy-to-4 phênyl) - carbomoyl] fluoro 2 methyl benzene thiocarboximidate

[158]

N-n-] - (phênyltrifluoromêthoxy and 4) carbamoylj - chlorophenyl 2 ethyl benzene thiocarboximidate

[159]

N - [D - (trifluoromethyl-4 phêhyl) - chlorophenyl 2 - carbamoyljbenzè - does thiocarboximidate ethyl '

[160]

N-n-[ - (dichloro 2.3 phenyl) - carbamoylj fluoro 2 benzêne-to-carboximidate ethyl

[161]

benzêne-to-carboximidate ethyl n-[the n - (chlorophenyl 2 methyl-3 phenyl) - carbomoyl] fluoro 2

[162]

N-£n - (difluoro 2.4 phenyl) - carbomoyl] fluoro 2 - carboximidatebenzêne ethyl

[163]

N-£n - (difluoro 2.4 phenyl) - carbomoyl] difluoro 2.4 benzêne-to-carboximidate ethyl

[164]

N-n-[ - (difluoro 2.4 phenyl) - carbomoyl] chloro 4 fluoro 2 benzêne-to-carboximidate ethyl

[165]

N-£n - (difluoro 2.4 phenyl) - carbomoyl] chloroacetamide 5 fluoro 2 benzêne-to-carboximidate ethyl

[166]

N-in - (difluoro 2.4 phenyl) - carbamoylj platinic 2 fluoro 6 benzêne-to-carboximidate ethyl

[167]

N [n-Lë - (difluoro 2.4 phenyl) - carbamoylj platinic 2 fluoro 4 benzêne-to-carboximidate ethyl

[168]

N-NC - (difluoro 2.4 phenyl) - carbomoyl] chloro 2 fluoro 5 benzêne-to-carboximidate ethyl

[169]

N-in - (dichloro 2.4 carboximidate of ëthylïphényl) - carbamoylj fluoro 2 benzêne-to-n-n-[ - (chlorophenyl 4 trifluoromethyl-2 phenyl) - carbamoylj fluoro 2 benzêne-to-carboximidate ethylJ

[170]

N-n-[ - (chlorophenyl 2 (methyl-1 ëthyl) -4 phenyl) carbamoylj fluoro 2 - carboximidate ethyl bamoyl (fluoro 2 benàène-to-carboximidate ethyl n-in - (a bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -2.4 phenyl) - because a-n-in - (a bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -2.4) - because - bamoyl] chloro 2 benzêne-to-carboximidate ethyl n-[the n - (substituted bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -2.4 phenyl) - because - bamoyl] difluoro 2.6 benzêne-to-carboximidate ethyl

[171]

N-NC - (a bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -2.4) - carbomoyl] chloro 2 fluoro 4 benzêne-to-carboximidate ethyl

[172]

bamoyl] chloro 2 fluoro 5 benzêne-to-carboximidate ethyl n-[the n - (substituted bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -2.4) - because -

[173]

2 - ΐ q7 8 -

[174]

N - [the n - (substituted bis - (chlorophenyl 2 trifludro L, 1.2 êthoxy) -2.4 phényDcarbamoyl] chloro 4 fluoro 2 benzëne-to-carboximidate ethyl

[175]

N -|Jn at - (a bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -2.4) carbomoyl] chloroacetamide 5 fluoro 2 benzëne-to-carboximidate ethyl

[176]

The n - n - 00 (the bis - (chlorophenyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -2.4 phenyl) carbomoyl] dichloride 2.4 benzëne-to-carboximidate ethyl

[177]

NT due - (chlorophenyl 2 phënyltrifluoromëthyl and 5) - carbamoylJ fluoro 2 benzëne-to-carboximidate ethyl

[178]

N - {n-- (difluoro 2.5 phenyl) - carbomoyl] dimethoxy-2.6 benzëne-to-carboximidate ethyl

[179]

N - [D - (difluoro 2.5 phênyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate. ethyl

[180]

N -&- (difluoro 2.6 phenyl) carbomoyl - dimethoxy-2.6 benzëne-to-carboximidate ethyl

[181]

N - n-|- (dichloro 2.6 phenyl) - carbomoyl] dimëthoxy-to-2.6 benzëne-to-carboximidate ethyl

[182]

N - {ir - (dibromo 2.6 phênyl) - carbomoyl]] dimethoxy-2.6 benzëne-to-carboximidate ethyl

[183]

N-n-[ - (dimethoxy-2.6 phenyl) - carbomoyl} dimethoxy-2.6 benzëne-to-carboximidate ethyl

[184]

N-n-] - (dimethyl-2.6 phênyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[185]

N - (n-- (dimethyl-2.6 phênyl) - carbomoyl] dimêthoxy-to-2.6 benzëne-to-carboximidate ethyl

[186]

N - [D - (êthyl and 2 methyl-6 phenyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[187]

N - (n-- (ethyl-2 mëthyl-to-6 phenyl) - carbomoyl] dimethoxy-2.6 benzëne-to-carboximidate ethyl

[188]

N - [D - (chloro-to-3 fluoro 4 phenyl) - carbomoyl] chloro 2 benzëne-to-carboximidate ethyl

[189]

N-Jn at - (chlorophenyl 3 fluoro 4 phênyl) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[190]

N - {n-- (fluoro 4 nitro 3 phenyl) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[191]

. - N-Jn at ((dimethyl-3.5 piperidinyl-1) -4 fluoro 3 phenyl) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[192]

the R - ls - 07821 n-[the n - ((dimethyl-3.5 piperidinyl-1) -4 fluoro 3 phenyl) - carbamoil ^] difluoro 2.6 ethyl benzene-carboximidate

[193]

N-£N - ((dimethyl-3.5 piperidinyl-1) -4 fluoro 3 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[194]

N-n-[ - (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[195]

N-n-[ - (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[196]

N-n-[ - (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] chloro 4 fluoro 2 ethyl benzene-carboximidate

[197]

N - [D - (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[198]

N - (n-- (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[199]

N-n-[ - (ehloro-to-4 trifluoromethyl-3 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[200]

N-n-[ - (chlorophenyl 3 trifluoromethoxy-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[201]

N-n-[ - (chlorophenyl 3 trifluoromethoxy-to-4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[202]

N-n-[ - (chlorophenyl 3 trifluoromethoxy-to-4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[203]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4) carbomoyl|platinic 2 ethyl benzene-carboximidate

[204]

N - {n-- (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 êthoxy) -4 phenyl) carbomoyl] fluoro 2 benzene-carboximidate of ëthle

[205]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[206]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 phenyl) carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[207]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 phenyl) carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[208]

N-Jn at - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl~4) carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[209]

N - {n-- (chlorophenyl 3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[210]

N - [D - (chlorophenyl 4 (chlorobenzyl 2 Trif or fluoro-L-, 1.2 ëthoxy) -3 phenyl) carbomoyl] fluoro 2 ethyl benzene-carboximidate

[211]

N - [D - (chlorophenyl 4 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -3 phenyl) carbomoyl] benzene-carboximidatechlioro and 2 ethyl

[212]

n-Jn at - (chlorophenyl 4 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -3 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[213]

N-n-[ - (chlorophenyl 4 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -3 phenyl) carbomoyl II-platinic 2 fluoro 6 ethyl benzene-carboximidate

[214]

N-Jn at - (chlorophenyl 4 (tétrafluo.ro and 1, 1, 2, 2 ethoxy) phenyl -3) - carbomoyl] fluoro 2 ethyl benzene rcarboximidate

[215]

N-n-[ - (chlorophenyl 4. (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -3 phenyl) carbomoyl ^] difluoro 2.6 ethyl benzene-carboximidate

[216]

N-n-[ - (chlorophenyl 3 trifluoromêthylthio-to-4 phenyl) - carbomoyl} platinic 2 ethyl benzene-carboximidate

[217]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthylthio) -4 phënyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[218]

N-n-[ - (chlorophenyl 4 trifluoromêthylthio-to-3 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[219]

N - n-|- (chlorophenyl 3 (dimethyl-3.5 piperidinyl-1) -4 phenyl) 3 - fluoro-to-2.6 carbamoil DIFs ethyl benzene-carboximidate

[220]

N-n-[ - ((the bis - (methyl-1-propyl) - amine) -4 platinic 3 phenyl) - benzene-carboximidatecarbamoyl3difluoro-to-2.6 ethyl

[221]

N - [D - (chloaro-a 3 cyano 4 phenyl) - carbomoyl] fluoro-to-2.6 DIFs ethyl benzene-carboximidate

[222]

N - [D - (chlorophenyl 3 (dimëthyl-to-1.1 ethoxycarbonyl) phenyl -4) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[223]

N - (a K - (chlorophenyl 3 ((mëthyl-to-1 ethyl) - L-methyl-2 propoxycarbonyl)~4 phenyl) - difluoro 2.6 carbamoy 13 ethyl benzene-carboximidate

[224]

N - Jn at - ' (chloro 3 (trimêthyl and 3, 5, 5 hexyloxycarbonyl) -4 phenyl) carbomoyl 3 difluoro 2.6 ethyl benzene-carboximidate

[225]

N - {n-- (chlorophenyl 3 méthy1-to-4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[226]

N-ül - (dichloro 3.4 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[227]

N-n-[ - (dichloro 3.4 phenyl) - carbomoyl] fluoro 3 ethyl benzene-carboximidate

[228]

N-Jn at - (dichloro 3.4 phenyl) - carbamoylj

[229]

ethyl boximidate

[230]

N-Jn at - (dichloro 3.4 phenyl) --carbamoyl] ethyl benzene-carboximidate

[231]

N-n-[ - (dichloro 3.4 phenyl) - carbamoylj

[232]

ethyl carboximidate

[233]

N-n-[ - (dichloro 3.4 phenyl) - carbamoylj

[234]

ethyl carboximidate

[235]

N-n-[ - (dichloro 3.4 phenyl) - carbamoylj

[236]

ethyl carboximidate

[237]

N-n-[ - (dichloro 3.4 phenyl) - ethyl benzene-carboximidatecarbamoylj

[238]

N-Jn at - (dichloro 3.4 phenyl) - ethyl benzene-carboximidatecarbamoylj

[239]

N - [D - (dichloro 3 and 4 phenyl) - carbamoylj

[240]

ethyl carboximidate

[241]

N - jjsï - (dichloro 3.4 phenyl) - carbamoylj

[242]

methyl 5 ethyl benzene-carboximidate

[243]

N - [D - (dichloro 3.4 phenyl) - ethyl benzene-carboximidatecarbamoylj

[244]

N - [D - (dichloro 3.4 phenyl) - ethyl benzene-carboximidatecarbamoylj

[245]

iodo 2 benzene because-chloro 2 - nitro 5 dichlorophenyl 2.4 benzene-dichloro 2.5 benzènepentafluoro-to-benzênetrif1uorométhoxy-to-3 trifluoromethoxy-to-4 methoxy-2 benzêne-nitrate 3 trifluoroacetic trifluoromëthyl-to-2 trifluoromëthyl and 3

[246]

N-n-[ - (trifluoromethoxy-to-4 trifluorométhy1-to-3 phenyl) - difluoro 2.6 carbamoylj ethyl benzene-carboximidate

[247]

N - [the n - ((chloro 2 trifluoroacetic 1.1, 2 ethoxy) phenyl -4 trifluoromêthyl and 3) - difluoro 2.6 carbamoylj ethyl benzene-carboximidate

[248]

N - [the n - ((tetrafluoro-1, 1, 2, 2 êthoxy) -4 trifluoromêthyl-to-3 phenyl) - difluoro 2.6 carbamoylj ethyl benzene-carboximidate

[249]

N - [the n - ((héxafluoro and 1, 1, 2, 3, 3, 3 propoxyl) -4 trifluoromethyl-3 phenyl) - difluoro 2.6 carbamoylj ethyl benzene-carboximidate

[250]

n-n-[ - (a bis - (difluoromethoxy) phenyl -3.4) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[251]

N - [GJs - (a bis - (trifluoromethoxy) phenyl -3.4) - difluoro 2.6 carbamoylj ethyl benzene-carboximidate

[252]

N - [D - (difluoro 2.2 substituted benzo [a dioxole-to-1,3j-to-yl 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[253]

" ^ w

[254]

N-ii.n - (IFFT fluoro-a 2, 2, 3 2:00, 3h benzo [dioxinne-to-1,4j - y1 and 6) - carbomoyl] chloro 2 benzêne-to-carboximidate ethyl

[255]

N-n-[ - (chlorophenyl 3 Trif or fluoro-a 2, 2, 3 ' 2:00, 3h benzo [dioxinne-to-1.4 ^ yl 6) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[256]

N-n-[ - (tetrafluoro-2, 2, 3, 3 2:00, 3h benzo [dioxinne-to-1.4] - y1 and 6) carbamoylJ fluoro 2 ethyl benzene-carboximidate

[257]

The ·Ν - (ν - (tetrafluoro-2.2 ., 3.3 2:00, 3h benzo [dioxinne-to-1.4] - yl 6) carbomoyl] chloro 2 ethyl benzene-carboximidate

[258]

N-n-[ - (tetrafluoro-2, 2, 3, 3 2:00, 3h benzo [dioxinne-to-l,-to-yl 6) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[259]

N-[the n - (difluoro 2.2 trifluoromethyl-3 2:00, 3h benzo [dioxinne-to-1.4] a-yl 6) - carbomoyl] benzene-carboximidate difluoro 2.6

[260]

D.1 ethyl

[261]

N - [D - (mëthyl and 3 (piperidinyl-1) -4 phenyl) - carbomoyl] difluoro 2.6 benzêne-to-carboximidate ethyl

[262]

N - (n-- (dimethyl-3.4 phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[263]

N-n-[ - (chlorophenyl 4 trifluoromethyl-3 phenyl) - carbomoyl] benzene-thiocarboximidate platinic 2 methyl

[264]

N-£n - (dichloro 3.4 phenyl) - carbomoyl] fluoro 2 benzêne-to-thiocarboximidate methyl

[265]

N - {n-- (dichloro .phényl 3,4) - carbomoyl] platinic 2 methyl benzene thiocarboximidate

[266]

N - Ijî - (dichloro 3.5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[267]

N - n-|- (bis-trifluoromethyl-3.5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[268]

N-bi - (dimethyl-3.5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[269]

N-n-[ - (ethylsulfonyl-to-3 trifluorométhy1-to-5 phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[270]

N - [the n - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 2.3 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[271]

N-£n - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 2.3 phenyl ") - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[272]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 2.3) - carbomoyl] dichloride 2.4 benzêne-to-carboximidate ethyl n - Jn at - (dichloro 2.3 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[273]

N - [D - (dichloro 2.3 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] dïfluoro-to-2.6 benzêne-to-carboximidate ethyl

[274]

N-Jn at - (dichloro 2.3 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] dichloride 2.4 benzêne-to-carboximidate ethyl

[275]

N-Jn at - (dichloro 2.3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) - phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[276]

N-[the n - (dichloro 2.3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) - phenyl) - carbomoyl] difluoro 2.6 benzêne-to-carboximidate ethyl

[277]

N-Jn at - (dichloro 2.3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) - phenyl) - carbomoyl] dichloride 2.4 benzêne-to-carboximidate ethyl

[278]

N - [D - (chlorophenyl 4 fluoro 2 methoxy-5 phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[279]

N - (n-- (chlorophenyl 4 fluoro 2 mëthoxy-to-5 phenyl) - carbomoyl] difluorô-to-2.6 benzêne-to-carboximidate ethyl

[280]

N - [D - (chlorophenyl 4 fluoro 2 methoxy-5 phenyl) - carbomoyl] difluoro 2.4 benzêne-to-carboximidate ethyl

[281]

N-Jn at - (chlorophenyl 4 fluoro 2 methoxy-5 phenyl) - carbomoyl] dimethoxy-2.6 benzêne-to-carboximidate ethyl

[282]

N - {n-- (chlorophenyl 4 fluoro 2 (methyl-1 ethoxy) phenyl -5) - carbomoyl] dimethoxy-2.6 benzêne-to-carboximidate ethyl

[283]

N - Jn at - (chlorophenyl 5 difluoro 2.4 phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[284]

N - (n-- (chlorophenyl 5 difluoro 2.4 phenyl) - carbomoyl] chloro 2 benzêne-to-carboximidate ethyl

[285]

N - n-|- (chlorophenyl 5 difluoro 2.4 phenyl) - carbomoyl] difluoro 2.6 benzêne-to-carboximidate ethyl

[286]

N - [D - (chlorophenyl 5 difluoro 2.4 phenyl) - carbomoyl] chloro 2 fluoro 6 benzêne-to-carboximidate ethyl

[287]

N-[ir - (chlorophenyl 5 difluoro 2.4 phenyl) - carbomoyl] dichloride 2.6 benzêne-to-carboximidate ethyl

[288]

N - {n-- (bromo 5 chloro 2 methyl-4 phenyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[289]

N - Canada provide - (phenyl trichloro 2, 4, 5) - carbomoyl] fluoro 2 benàène-to-carboximidate ethyl

[290]

N-n-[ - (trifluoromethyl 2, 4, 6 phënyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[291]

N-n-[ - (trifluoromethyl 2, 4, 6 phenyl) - carbamoil! dimëthoxy-to-2.6 ethyl benzene-carboximidate

[292]

N-n-[ - (phenyl trichloro 2, 4, 6) - carbomoyl] dimethoxy-2.6 ethyl benzene-carboximidate

[293]

N-NC - (chlorophenyl 3 (chlorophenyl 3 propene-2 yloxy group) -4 phënyltrifluoromëthyl and 5) - carbamoil!) difluoro 2.6 ethyl benzene-carboximidate

[294]

N - 00 the n - (chlorophenyl 3 (bromo 3 propene-2 yloxyj-to-4 trifluoromëthyl and 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[295]

N-in - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 methyl-5 phenyl) - carbomoyl] fluoro 2 ethyl benzene carboximidatè

[296]

N-n-[ - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 méhhyl-to-5 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[297]

N-NC - (chlorophenyl 3 (chlorô-to-2 trifluoromethyl 1, 1, 2. ëthoxy) -4 phënylmëthyl and 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[298]

N-NC - (chlorophenyl 3 (chlorobenzyl 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 methyl-5 phënyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[299]

N-NC - (chlorophenyl 3 methyl-5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[300]

N-NC - (chlorophenyl 3 mëthyl and 5 (tetrafluoro-1, 1, 2, 2 ëthoxy) -4 phënyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[301]

N-Dî - (chlorophenyl 3 mëthyl and 5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[302]

N-fn-- (chlorophenyl 3 mëthyl and 5 (tëtrafluoro and 1, 1, 2, 2 ëthoxy) -4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[303]

N-ûï - (chlorophenyl 3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 methyl-5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[304]

N-n-[ - (chlorophenyl 3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 methyl-5 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[305]

N-NC - (chlorophenyl 3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 methyl-5 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[306]

N-NC - (chlorophenyl 3 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 methyl-5 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[307]

n-NC - (bis trifluorométhÿl above 3.5 platinic 4 phenyl) - carbamoil fluoro 2 ethyl benzene-carboximidate

[308]

N-Jn at - (bromo 3 (chlorophenyl 3 propene-2 yloxy group) -4 trifluoromethyl-5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[309]

N-Jn at - (bromo 3 (propene-2 yloxy group) -4 trifluoromethyl-5 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[310]

N-n-[ - (bromo 3 chloro 5 (chlorophenyl 3 propene-2 yloxy group) -4 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[311]

N - {n-- (bromo 3 chloro 5 (propêne-to-2 yloxy group) -4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[312]

N - [D - (dichloro 3.5 difluoromëthoxy-to-4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[313]

N-Jn at - (chlorodifluorométhoxy-to-4.dichloro above 3.5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[314]

N - (n-- (dichloro 3.5 trifluoromëthoxy-to-4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[315]

N - n-|- ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[316]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[317]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - chlorophenyl 2 mëthoxy-to 6 benzene-carboximidate D.1 ethyl

[318]

N - (n-- ((ëhloro-to-2 trifluoroacetic 1.1 and 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.4 ethyl benzene-carboximidate

[319]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[320]

N-Jn at - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl - chlorophenyl 4! fluoroorganic 2 ethyl benzene-carboximidate

[321]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbomoyl] chloroacetamide 5 fluoro 2 ethyl benzene-carboximidate

[322]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - chlorophenyl 2 fluoro 6 ethyl benzene-carboximidate

[323]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - chlorophenyl 2 fluoro 4 ethyl benzene-carboximidate

[324]

N-is - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl -! platinic 2 fluoro 5 ethyl benzene-carboximidate

[325]

N-n-[ - ((chloro 2 trifluoro-L, L-/ 2; ethoxy) phenyl -4 dichloroallyloxy 3.5) 13 - carbamoydicnloro-to-2.4 bénzène-to-carboximidate ethyl

[326]

N - NC - ((chloro 2-trifluoro-L-, 1.2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[327]

N-NC - ((chloro 2-trifluoro-L-, 1.2 ëthoxy) -4 dichloroallyloxy 3.5 phenyl) - carbamoyIJ dichloroallyloxy 3.4 ethyl benzene-carboximidate

[328]

N-ûî - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - dichloride 3.5 carbamoylj ethyl benzene-carboximidate

[329]

N-iq - ((chloro 2 trifluoro-L, 1? 1 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbamoylJdifluoromëthoxy and 2 ethyl benzene-carboximidate

[330]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! (trifiuoro-a 2, 2, 2 ethoxy) ethyl -2 benzêne-to-carboximidate

[331]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - substituted bis-carbamoyl -! (trifiuoro-a 2, 2, 2 ethoxy) ethyl benzene-carboximidate -2.6

[332]

N-Lnis - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5)! - carbamoil mêthoxy and 2 ethyl benzene-carboximidate

[333]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - dimethoxy-2.6 ethyl benzene-carboximidate

[334]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5)! - carbamoil difluoromëthylthio and 2 ethyl benzene-carboximidate

[335]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 ëthôxy) -4 dichloroallyloxy 3.5 phenyl) - carbamoil! difluoromëthylsulfinyl-to-2 benzêne-to-carboximidate ethyl

[336]

Web-n-NC - ((fchloro-to-2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5)! - carbamoil difluoromëthylsulfonyl and 2 ethyl benzene-carboximidate

[337]

N-qii - ((chloro 2 Trif or fluoro-L-, 11, -2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - trifluoromethyl-2 ethyl benzene-carboximidate

[338]

N-R4II - ((chloro 2-trifluoro-L-, 1.2 ethoxy) -4 dichloride 3the I5 phenyl) - carbamoil! methyl 2 ethyl benzene-carboximidate

[339]

N-NC - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5-phenyl) - carbomoyl} fluoro 2 benzëne-to-carboximidate of ëthyle

[340]

N - [the n - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - chlorophenyl 2 carbamoyUbenzëne-to-carboximidate ethyl

[341]

N-NC - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate of ëthyle

[342]

N-n-[ - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbomoyl] chloro 2 fluoro 6 benzëne-to-carboximidate ethyl

[343]

N-one - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) 11 - carbamoy dichloroallyloxy 2.6 benzëne-to-carboximidate of ëthyle

[344]

N-NC - ((bromo 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - carbomoyl] dichloride 2.4 benzëne-to-carboximidate of ëthyle

[345]

N-Dî - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 benzëne-to-carboximidate benzyl

[346]

N-NC - (dichloro 3.5 (tëtrafluoro-to-1>1, 2, 2 ethoxy) phenyl -4) carbomoyl! fluoro 2 benzëne-to-carboximidate of chloro-4 benzyl

[347]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 benzëne-to-carboximidate methyl

[348]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[349]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! fluoro 2 benzëne-to-carboximidate trifluoro-2, 2, 2 ethyl

[350]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 benzëne-to-carboximidate dismutating 2, 2, 2 ethyl

[351]

N-NC - (dichloro 3 thereof, 5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] fluoro 2 nitro 5 benzëne-to-carboximidate ethyl

[352]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] chloro 2 benzëne-to-carboximidate of ëthyle

[353]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] chloro 4 benzëne-to-carboximidate of ëthyle

[354]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] difluoro 2.4 benzëne-to-carboximidate of ëthyle

[355]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl] difluoro 2.6 benzëne-to-carboximidate of ëthyle

[356]

N-£N - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! chloro 4 fluoro 2 benzêne-to-carboximidate ethyl

[357]

N-Dî - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! chlor-5 fluoro 2 benzêne-to-carboximidate ethyl

[358]

N-NC - (dichlorophenyl 3, 5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! platinic 2 fluoro 6 benzêne-to-carboximidate ethyl

[359]

N-NC - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! platinic 2 fluoro 4 benzêne-to-carboximidate ethyl

[360]

N-[.N - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! chch.loro and 2 fluoro 5 benzêne-to-carboximidate ethyl

[361]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! platinic 2 methoxy-6 benzêne-to-carboximidate ethyl

[362]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! dichloro 2.4 benzêne-to-carboximidate ethyl

[363]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! dichloro 2.6 benzêne-to-carboximidate ethyl

[364]

N-Qj - (dichloro 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! dichloro 3.4 benzêne-to-carboximidate D.1 ethyl

[365]

N-NC - (dichloro 3.5 (tétrafiuoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! dichloro 3.5 benzêne-to-carboximidate ethyl

[366]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! difluoromëthoxy-to-2 benzêne-to-carboximidate ethyl

[367]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! (trifluoromethyl 2, 2, 2 ethoxy) ethyl -2 benzêne-to-carboximidate

[368]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! the bis - (trifluoromethyl 2, 2, 2 ethoxy) ethyl -2.6 benzëne-to-carboximidate

[369]

N-in - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! methoxy-2 benzêne-to-carboximidate ethyl

[370]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! dimethoxy-2.6 benzêne-to-carboximidate ethyl

[371]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! methylsulfonyloxy-to-2 benzêne-to-carboximidate ethyl

[372]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! difluoromêthylthio-to-2 benzêne-to-carboximidate ethyl

[373]

N-NC - (dichloro 3.5 (tëtrafluoro I, 1, 2, 2 ethoxy) -4 phênyl) carbomoyl! difluorométhylsulfinyl-to-2 benzêne-to-carboximidate ethyl

[374]

N-one - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ëthoxy) -4 phênyl} carbamoylJdifluoromëthylsulfonyl-to-2 benzëne-to-carboximidate ethyl

[375]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl-carbamoyl -4]] mëthyl-to-2 benzëne-to-carboximidate ethyl

[376]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl-carbamoyl -4] trifluoromethyl-2 benzëne-to-carboximidate ethyl

[377]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl-carbamoyl -4] fluoro 2 benzëne-to-carboximidate propyl

[378]

N-0n - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl-carbamoyl -4! fluoro 2 benzëne-to-carboximidate allyl

[379]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ëthoxy) carbomoyl -4 phënyl! fluoro 2 benzëne-to-carboximidate propargyl

[380]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl-carbamoyl -4! fluoro 2 benzëne-to-carboximidate butyl

[381]

N-NC - (dichloro 3.5 (ëthoxytêtrafluoro and 1, 1, 2, 2) carbomoyl -4 phënyl! fluoro 2 benzëne-to-carboximidate hexyl

[382]

n-NC - (dichloro 3.5 (têtrafluoro and 1, 1, 2, 2 ethoxy) -4 phënyl) carbomoyl 1 fluoro 2 benzëne-to-carboximidate cyclohexyl

[383]

N-NC - ((dibromo 2.2 difluoro 1.1 ëthoxy) -4 dichloroallyloxy 3.5 phênyl) --carbamoyl] ethyl-anomer 2.6 carboximidate

[384]

N-NC - ((dichloro 2.2 difluoro 1.1 ëthoxy) -4 dichloroallyloxy 3.5 phenyl) - carbamoil! difluoro 2.6 benzëne-to-carboximidate ethyl

[385]

N-NC - ((chloro 2 difluoro 1.1 ëthoxy) -4 dichloroallyloxy 3.5 phenyl) carbomoyl! difluoro 2.6 benzëne-to-carboximidate ethyl

[386]

N-NC - (dichloro 3.5 phênylpentafluoréthoxy and 4) carbomoyl! - difluoro 2.6 benzëne-to-carboximidate'd ' ^ ^ SD L-th

[387]

N-NC - (dichloro 3.5 (dichloride 1.2 difluoro 1.2 ethoxy) -4 phênyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[388]

N-NC - (dichloro 3 ., 5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phênyl) - carbomoyl] fPüoro-to-2 benzëne-to-carboximidate ethyl

[389]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] chloro 2 benzëne-to-carboximidate LID ' ethyl

[390]

N-n-[ - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phënyl) - carbomoyl] chloro 2 methoxy-6 benzëne-to-carboximidate ethyl

[391]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] difluoro 2.4 benzëne-to-carboximidate ethyl

[392]

N-iq - (dichloro 3.5 (hexafl'uoro and 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[393]

N-NC - - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! chloro 4 fluoro 2 benzene-carboximidate of ëthyle

[394]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! chlor-5 fluoro 2 ethyl benzene-carboximidate

[395]

N-£N - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phënyl) carbomoyl! - chlorophenyl 2 fluoro 6 ethyl benzene-carboximidate

[396]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phênyl) carbomoyl! - chlorophenyl 2 fluoro 4 ethyl benzene-carboximidate

[397]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phênyl) carbomoyl! - chlorophenyl 2 fluoro 5 ethyl benzene-carboximidate

[398]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! dichloroallyloxy 2.4 benzene-carboximidate'd ' ethyl

[399]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! dichloro 2.6 ethyl benzene-carboximidate

[400]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbamoil! dichloroallyloxy 3.4 ethyl benzene-carboximidate

[401]

N-Dî - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! dichloro 3.5 ethyl benzene-carboximidate

[402]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbamoil! difluoromëthoxy and 2 ethyl benzene-carboximidate

[403]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! (trifluoromethyl 2, 2, 2 ethoxy) ethyl benzene-carboximidate -2

[404]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - carbamoil! the bis - (trifluoromethyl 2, 2, 2 ethoxy) ethyl -2.6 benzêne-to-carboximidate '

[405]

N-NC - (dichloro 3.5 (hëxafluoro and 1, 1, 2, 3, 3, 3 propoxyl) -4 phënyl)! - carbamoil mëthoxy and 2 ethyl benzene-carboximidate

[406]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - benzene-carboximidatecarbamoyUdiméthoxy-to-2.6 ethyl n-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2therein 3, 3, 3 propoxyl) -4 phenyl) - carbamoil! difiuoromëthylthio-to-2 benzëne-to-carboximidate ethyl

[407]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phënyl)! - carbamoil difluorométhylsulfinyl-to-2 benzëne-to-carboximidate ethyl

[408]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phêny1) - carbamoysubscribesdifluorométhylsulfonyl-to-2 benzëne-to-carboximidate ethyl

[409]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - trifluoromethyl-2 11 carbamoybenzëne-to-carboximidate ethyl

[410]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) 11 - carbamoymêthyl-to-2 benzëne-to-carboximidate ethyl

[411]

N-NC - (dichloro 3.5 (octafluoro 1, 1, 2, 3, 3, 4, 4, 4-butyloxy) phenyl -4) - difluoro 2.6 carbamoyilbenzëne-to-carboximidate ethyl

[412]

N-NC - (dichloro 3.5 (trifluoromethyl 2, 2, 2 ethoxy) phenyl -4)! fluoro 2 - carbamoil benzëne-to-carboximidate ethyl

[413]

N-NC - (dichloro 3.5 (trifluoromethyl 2, 2, 2 ethoxy) phenyl -4) carbomoyl! - chlorophenyl 2 benzëne-to-carboximidate ethyl

[414]

N-R4II - (dichloro 3.5 (trifluoromethyl 2, 2, 2 ethoxy) phenyl -4) - carbamoyl3difluoro-to-2.6 benzëne-to-carboximidate ethyl

[415]

N-in - (dichloro 3.5 (trifluoromethyl 2, 2, 2 ethoxy) phenyl -4) carbomoyl -! dichloro 2.4 benzëne-to-carboximidate ethyl

[416]

N-NC - (dichloro 3.5 (tetrafluoro-2, 2, 3, 3 propoxyl) -4 phenyl) carbomoyl! fluoro 2 benzëne-to-carboximidate ethyl

[417]

N-NC - (dichloro 3.5 (tetrafluoro-2, 2, 3, 3 propoxyl) -4 phenyl) carbomoyl! platinic 2 benzëne-to-carboximidate ethyl

[418]

N-NC - (dichloro 3.5 (tetrafluoro-2, 2, 3, 3 propoxyl) -4 phenyl) carbomoyl! difluoro 2.6 benzëne-to-carboximidate ethyl

[419]

N-NC - (dichloro 3.5 (tetrafluoro-2, 2, 3, 3 propoxyl) -4 phenyl) carbomoyl! dichloro 2.4 benzëne-to-carboximidate ethyl

[420]

N-NC - (dichloro 3.5 (hexafluoroisopropyl 2, 2, 3, 4, 4, 4-butyloxy) phenyl -4) carbomoyl -! difluoro 2.6 benzëne-to-carboximidate ethyl

[421]

N-NC - (dichloro 3.5 (heptafluoro 2, 2, 3, 3, 4, 4, 4-butyloxy) phenyl -4) carbomoyl! - difluoro 2.6 benzëne-to-carboximidate ethyl

[422]

N-NC - (dichloro 3.5 (octafluoro 2, 2, 3, 4, 4, 5, 5, 5 pentyloxy) phenyl -4) carbomoyl! - difluoro 2.6 benzëne-to-carboximidate ethyl n-cc.n - ((chloro 4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl - 1 fluoro 2 ethyl benzene-carboximidate

[423]

N-NC - ((chloro 4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl - j-difluoro 2, 6 ethyl benzene-carboximidate

[424]

N-NC - (dichloro 3.5 (trifluoromethyl-4 a benzyloxy) phenyl -4) carbomoyl! fluoro 2 ethyl benzene-carboximidate

[425]

N-NC - (dichloro 3.5 (trifluoromethyl-4 a benzyloxy) phenyl -4) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[426]

N-R4II - ((chloro 3 trifluoromethyl-3 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[427]

N-NC - ((chloro 3 trifluoromethyl-3 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[428]

N-NC - ((chioro-to-2 trifluoromethyl-4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[429]

N-NC - ((chloro 2 trifluoromethyl-4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[430]

N-NC - (dichloro 3.5 (nitro 4 a benzyloxy) phenyl -4) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[431]

- N-NC - (dichloro 3.5 (nitro 4 a benzyloxy) phenyl -4) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[432]

N-NC - ((dichloride 2.4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[433]

N-NC - ((dichloride 2.4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[434]

N-NC - ((cyano 4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[435]

N-NC - ((cyano 4 a benzyloxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[436]

N-NC - (dichloro 3.5 (trifluoromethoxy-to-4 a benzyloxy) phenyl -4) carbomoyl! fluoro 2 benzene-carboximidate. ethyl

[437]

N-NC - (dichloro 3.5 (trifluoromethoxy-to-4 a benzyloxy) phenyl -4} carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[438]

N-NC - (benzyloxy 4 dichloro 3.5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[439]

N-NC - (dichloro 3.5 (fluoro 4 a benzyloxy) phenyl -4) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[440]

N-NC - (dichloro 3.5 pentafluorobenzyloxy-to-4 phenyl) 3 - carbamoil difluoro 2.6 benzëne-to-carboximidate ethyl

[441]

N-NC - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) - carbomoyl] fluoro 2 benzëne-to-carboximidate ethyl

[442]

•5 n-NC - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) 3 - chlorophenyl 2 carbamoil benzëne-to-carboximidate ethyl

[443]

N-NC - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) 3 - carbamoil difluoro 2.6 benzëne-to-carboximidate ethyl

[444]

N-NC - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) carjqbamoyll - chlorophenyl 4 fluoro 2 benzëne-to-carboximidate ethyl

[445]

N-£n - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) carbomoyl! - chlorophenyl 2 fluoro 6 benzëne-to-carboximidate ethyl

[446]

N-NC - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) 3 - chlorophenyl 2 carbamoil fluoroorganic 4 benzëne-to-carboximidate ethyl

[447]

15 N-Qj - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) - carbamoil! platinic 5 fluoro 2 benzëne-to-carboximidate ethyl

[448]

N cu - (dichloro 3.5 (dichloride 1.2 éthényloxy) -4 phenyl) - carbamoil dichloroallyloxy 2.4 benzëne-to-carboximidate ethyl

[449]

N-NC - ((chloro 3 propene-2 yloxy group) -4 dichloroallyloxy 3.5 phenyl) - 2q carbamoil! difluoro 2.6 benzëne-to-carboximidate ethyl

[450]

N-NC - ((bromo 3 propëne-to-2 yloxy group) -4 dichloroallyloxy 3.5 phenyl) carbomoyl! difluoro 2.6 benzëne-to-carboximidate ethyl

[451]

N-£n - (allyloxy 4 dichloro 3.5 phenyl) - carbamoylUdifluoro-to-2.6 benzëne-to-carboximidate of éthy ^ th

[452]

25 N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbamoy 13 fluoro 2 benzëne-to-carboximidate ethyl

[453]

N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbomoyl} platinic 2 benzëne-to-carboximidate ethyl

[454]

N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbomoyl] 3q difluoro 2.6 benzëne-to-carboximidate ethyl

[455]

N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbomoyl} platinic 4 fluoro 2 benzëne-to-carboximidate ethyl

[456]

N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbomoyl} platinic 2 fluoro 4 benzëne-to-carboximidate ethyl

[457]

35 N-NC - (dichloro 3.5 difluorométhylthio-to-4 phenyl) - carbomoyl] dichloride 2.4 benzëne-to-carboximidatedêthyle

[458]

the L

[459]

N-QSJ - (chlorodifluorométh.ylthio-to-4 dichloro 3.5 phenyl) carbomoyl fluoroorganic 2! ethyl benzene-carboximidate

[460]

N-NC - (chlorodifluorométhylthio-to-4 dichloro 3.5 phenyl) carbomoyl! platinic 2 ethyl benzene-carboximidate

[461]

•n-NC - (chlorodifluorométhylthio-to-4 dichloro 3.5 phenyl) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[462]

N-NC - (dichloro 3.5 trifluoromêthylthio-to-4 phenyl) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[463]

The DSL - n - (dichloro 3.5 trifluoromethylthio and 4 phenyl) carbomoyl - chlorophenyl 2! j of ethyl benzene carboximidate

[464]

N-NC - (dichloro 3.5 trifluoromethylthio and 4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[465]

N-Dî - ((chloro 2 trifluoromethyl 1, 1, 2 ethylthio) phenyl -4 dichloroallyloxy 3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[466]

5 N-£N - ((chloro 2 trifluoromethyl 1, 1, 2 ethylthio) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[467]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethylthio) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[468]

N-NC " ((chloro 2 trifluoromethyl 1, 1, 2 ethylthio) -4 dichloroallyloxy 3.5 P-phenyl) - carbamoil! dichloroallyloxy 2.4 ethyl benzene-carboximidate

[469]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethylthio) phenyl -4) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[470]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethylthio) phenyl -4) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[471]

5 N-n-[ - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethylthio) phenyl -4) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidateiF.

[472]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethylthio) phenyl -4)! - carbamoil dichloroallyloxy 2.4 ethyl benzene-carboximidate

[473]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propylthio) -4

[474]

g-phenyl) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[475]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propylthio) -4 phenyl) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[476]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propylthio) -4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[477]

5 N-NC "(dichloride 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3" 3 propylthio) -4 phenyl) - carbamoil! dichloroallyloxy 2.4 benzene-carboximidate ethyl n-NC - ((bromo 3 propene-2 ylthio) -4 dichloroallyloxy 3.5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[478]

N-NC- ((chloro 3 propene-2 ylthio) phenyl -4 dichloroallyloxy 3.5) carbomoyl 3 - difluoro 2.6 ethyl benzene-carboximidate

[479]

N-NC - (dichloro 3.5 (pyrrolidinyl 1) -4 phenyl) - carbamoyil fluoro 2 ethyl benzene-carboximidate

[480]

N-cc.n - (dichloro 3.5 (pyrrolidinyl 1) -4 phenyl) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[481]

N-NC - (dichloro 3.5 (pyrrolidinyl 1) -4 phenyl) - difluoro 2.6 carbamoyH ethyl benzene-carboximidate

[482]

N - (GJs - (dichloro 3.5 (pyrrolidinyl 1) -4 phenyl) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[483]

N-is - (dichloro 3.5 (morpholinylethyl 4) -4 phenyl) - difluoro 2.6 carbamoyil ethyl benzene-carboximidate

[484]

N-NC - (dichloro 3.5 (methyl-4 pipêrazinyl) -1) -4 phenyl) carbomoyl 1 difluoro 2.6 ethyl benzene-carboximidate

[485]

N-0sj - (dibromo 3.5 (pyrrolidinyl 1) -4 phenyl) - difluoro 2.6 carbamoy 11 ethyl benzene-carboximidate

[486]

N-ûj - (dibromo 3.5 (pipêridinyl-to-1) -4 phenyl) - difluoro 2.6 carbamoyil ethyl benzene-carboximidate

[487]

N-NC - ((-allyl-, n-methylamino) phenyl -4 dichloroallyloxy 3.5) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[488]

N-is - ((-allyl-, n-butylamino) phenyl -4 dichloroallyloxy 3.5) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[489]

N-NC - (dichloro 3.5 (n-, N-dimethylamino) phenyl -4) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[490]

N-NC - ((n-- (chlorophenyl 3 ally), n mëthylamino) -4 dichloroallyloxy 3.5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[491]

N-£N " C. (the n - (bromo 3 ally), n mëthylamino) -4 dichloroallyloxy 3.5 phenyl). 11 - carbamoy-anomer 2.6 ethyl benzene-carboximidate

[492]

N-one - ((n-- (bromo 3 ally), n-methylamino) phenyl -4 dichloroallyloxy 3.5) 11 - carbamoy-anomer 2.6 ethyl benzene-carboximidate

[493]

N-NC - ((n-- (bromo 3 ally), n-butylamino) -4 dichloroallyloxy 3.5 phenyl) - difluoro 2.6 carbamoy ^ 11 ethyl benzene-carboximidate

[494]

N-NC " ((the n - (chlorophenyl 3 ally) - n-butylamino) -4 dichloroallyloxy 3.5 phenyl) - difluoro 2.6 carbamoy 11 benzene-carboximidate ethyl n - (DD - (dichloro 3.5 (the m-methyl, or n-propargylamino) -4 phenyl) carbomoyl] difluoro 2.6 benzêne-to-carboximidate ethyl

[495]

N - ([n-- (dichloro 3.5 (n ëthyl, -n-propargylamino) -4 phenyl) carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[496]

N - (n-- (dichloro 3.5 (the n, n dipropargylamino) -4 phenyl) carbomoyl} difluoro 2.6 benzêne-to-carboximidate ethyl

[497]

N-NC - (dichloro 3.5 (n-methyl, n-propyl-amino) phenyl -4) carbomoyl} dichloroallyloxy 2.6 benzêne-to-carboximidate ethyl ^

[498]

N-qii - (dichloro 3.5 (n-methyl, n-propyl-amino) phenyl -4) carbomoyl} difluoro 2.6 benzëne-to-carboximidate ethyl

[499]

N-NC - (cyano 4 dichloro 3.5 phenyl) - carbomoyl} fluoro 2 benzëne-to-carboximidate ethyl

[500]

N-qii - (cyano 4 dichloro 3.5 phenyl) - carbomoyl} platinic 2 benzëne-to-carboximidate ethyl

[501]

N-n-[ - (cyano 4 dichloro 3.5 phenyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[502]

N-qu - (cyano 4 dichloro 3.5 phenyl) - carbomoyl] dichloride 2.4 benzëne-to-carboximidate ethyl

[503]

N-NC - (dichloro 3.5 (dimethyl-1.1 ethoxycarbonyl) phenyl -4) carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[504]

N-NC- (dichloride 3.5 ((methyl-1 Chloroethyl) -1 methyl 2 propoxycarbonyl) -4 phenyl) - carbomoyl} difluoro 2.6 ethyl benzene-carboximidate

[505]

N-NC - (dichloro 3.5 -4 (heptyloxycarbonyl) phenyl) - carbomoyl} difluoro 2.6 benzêne-to-carboximidate ethyl

[506]

N-R4II - (dichloro 3.5 (trimethyl-3, 5, 5 hexyloxycarbonyl) -4 phenyl) - carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[507]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dibromo 3.5) carbomoyl! - difluoro 2.6 benzëne-to-carboximidate ethyl

[508]

N-NC - (dibromo 3.5 (tëtrafluoro and 1, 1, 2, 2 ethoxy) -4F.phenyl) carbomoyl], difluoro 2.6 benzëne-to-carboximidate ethyl

[509]

N-NC - (dibromo 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) carbomoyl] difluoro 2.6 benzëne-to-carboximidate ethyl

[510]

N-NC - (bis trifluoromêthyl above 3.5 difluoromëthoxy-to-4 phenyl) carbamoylO difluoro 2.6 benzëne-to-carboximidate ethyl -■> N-NC - (bis trifluoromêthyl and 3.5 (chlorobenzyl 2 trifluoroacetic 1 ,l, 2 ethoxy) phenyl -4) - carbomoyl} difluoro 2.6 ethyl benzene-carboximidate

[511]

N-qs1 - (bis IFFT luorométhyl and 3.5 (têtraf fluoro-a 1, 1, 2, 2 êthoxy) -4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[512]

N-cc.n - (bis IFFT luorométhyl and 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - difluoro 2.6 carbamoil! ethyl benzene-carboximidate

[513]

N-qii - (difluoromethoxy-4 dimethyl-3.5 phenyl) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[514]

N-NC - (chlorodifluorométhoxy-to-4 dimethyl-3.5 phenyl) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[515]

N-n-[ - (dimethyl-3.5 trifluoromethoxy-to-4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[516]

N-NC - ((chloro 2 trifl.uoro and 1, 1, 2 ethoxy) phenyl -4 dimethyl-3.5) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[517]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl dimethyl-3.5 -4) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[518]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 dimethyl-3.5 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[519]

N-£N - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl dimethyl-3.5 -4)! - carbamoil dichloroallyloxy 2.4 ethyl benzene-carboximidate

[520]

N-NC~(dimethyl-3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! fluoro 2 ethyl benzene-carboximidate

[521]

N-NC - (dimethyl-3.5 (têtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! platinic 2 ethyl benzene-carboximidate

[522]

N-NC - (dimethyl-3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[523]

N-NC - (dimêthyl and 3.5 (tétraf fluoro-a 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! dichloro 2.4 ethyl benzene-carboximidate

[524]

N-cc.n - (dimethyl-3.5 (tétraf fluoro-a 1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! platinic 2 fluoro 4 ethyl benzene-carboximidate

[525]

N-NC - (dimethyl-3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbamoil! fluoro 2 ethyl benzene-carboximidate

[526]

N-NC - (dimethyl-3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[527]

N-NC - (dimethy1 and 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4-phenyl) - difluoro 2.6 carbamoil! ethyl benzene-carboximidate

[528]

N-£N - (dimethyl-3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - dichloride 2.4 carbamoyll ethyl benzene-carboximidate

[529]

5 N-NC - ((dichloride 1.2 éthényloxy) -4 dimethyl-3.5 phenyl) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[530]

N-NC - (chlorophenyl 3 (dichloride 1.2 éthényloxy) -4 methyl-5 phënyl) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[531]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) thiocarbamoyl group! ^ difluoro 2.6 ethyl benzene-carboximidate

[532]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) - thiocarbamoyl group! difluoro 2.6 ethyl benzene-carboximidate

[533]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - thiocarbamoyl group! difluoro 2.6 ethyl benzene-carboximidate

[534]

L5 n-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) carbomoyl! difluoro 2.6 benzêne-to-thiocarboximidate ethyl

[535]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 dichloroallyloxy 3.5) carbomoyl! - difluoro 2.6 benzene thiocarboximidate

[536]

ethyl

[537]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbamoil! difluoro 2.6 ethyl benzene thiocarboximidate

[538]

N-NC - (dichloro 3.5 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) thiocarbamoyl group! difluoro 2.6 ethyl benzene thiocarboximidate

[539]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 dichloroallyloxy 3.5

[540]

25 phenyl) - thiocarbamoyl group! difluoro 2.6 ethyl benzene thiocarboximidate

[541]

N-NC - (dichloro 3.5 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - thiocarbamoyl group! difluoro 2.6 ethyl benzene thiocarboximidate

[542]

N-NC - (dichloro 3.5 (difluoromethoxy) phenyl -4 fluoro 2) carbomoyl! fluoro 2 ethyl benzene-carboximidate

[543]

N-NC - (chlorodifluorômêthoxy-to-4 dichloro 3.5 fluoro 2 phenyl) - carbamoil! difluoro 2.6 ethyl benzene-carboximidate

[544]

N-NC - (dichloro 3.5 flüoro-to-2 trifluoromethoxy-to-4 phenyl) carbomoyl! difluoro 2.6 ethyl benzene-carboximidate

[545]

N-NC - (bromo 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[546]

N-NC - ((chloro 2 IFFT ΐ 1101:07 ΐ, 1.2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[547]

-heterocylic £N - {(chlorobenzyl 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) carbomoyl! - chlorophenyl 2 ethyl benzene-carboximidate

[548]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] difluoro 2.4 ethyl benzene-carboximidate

[549]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5.

[550]

fluoro 2 phênyl) carbomoyl! - difluoro 2.6 ethyl benzene-carboximidate

[551]

N-NC - ((chloro 2 trifl'uoro L, 1.2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) 3 - chlorophenyl 4 carbamoil fluoroorganic 2 ethyl benzene-carboximidate

[552]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbamoil. J-platinic 2 fluoro 4 ethyl benzene-carboximidate

[553]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] benzene-carboximidatedichlorô-to-2.4 ethyl

[554]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] difluoromethoxy-2 ethyl benzene-carboximidate

[555]

N-NC - {(chlorobenzyl 2 trifluoromethyl 1, 1, 2 ethoxy) -4 dichloroallyloxy 3.5 fluoro 2 phenyl) - carbomoyl] (trifluoromethyl 2, 2, 2 ethoxy) ethyl benzene-carboximidate -2

[556]

N-NC - (dichloro 3.5 fluoro 2 (têtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[557]

N-NC - (dichloro 3.5 fluoro 2 (tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[558]

N-NC - (dichloro 3.5 fluoro 2 (têtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[559]

N-NC - (dichloro 3.5 fluoro 2 (têtrafluoro and 1, 1, 2, 2 ethoxy) phenyl -4) - carbomoyl] benzene-carboximidate dichloroallyloxy 2.4 ethyl n-NC - (dichloro 3" 5 fluoro 2 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbamoyU fluoro 2 ethyl benzene-carboximidate

[560]

N-NC - (dichloro 3.5 fluoro 2 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) 3 - chlorophenyl 2 carbamoil benzene-carboximidate ethyl

[561]

N-NC - (dichloro 3.5 fluoro 2 (hexafluoroantimonic the I, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[562]

N-NC - (dichloro 3.5 fluoro 2 (hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl) 13 - carbamoy dichloroallyloxy 2.4 ethyl benzene-carboximidate

[563]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - benzene-carboximidatecarbamoyllfluoro and 2 ethyl

[564]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[565]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbamoylldifluo-to-a ro-2, 4 ethyl benzene-carboximidate

[566]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbamoyl3chloro-to 4 fluoro 2 ethyl benzene-carboximidate

[567]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} platinic 5 fluoro 2 ethyl benzene-carboximidate '

[568]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} platinic 2 fluoro 6 ethyl benzene-carboximidate

[569]

N-Dî - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} platinic 2 fluoro 4 ethyl benzene-carboximidate

[570]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} platinic 2 fluoro 5 ethyl benzene-carboximidate

[571]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} dichloroallyloxy 2.4 ethyl benzene-carboximidate

[572]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[573]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl] difluoromethoxy-2 ethyl benzene-carboximidate

[574]

N-cn - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl] (trifluoromethyl 2, 2, 2 ethoxy) ethyl benzene-carboximidate -2

[575]

N-NC - (dichloro 3.5 difluoro 2.4 phenyl) - thoxy-to-2 carbamoyll say, 6 ethyl benzene-carboximidate

[576]

N-£n - (dichloro 3.5 difluoro 2.4 phenyl) - carbomoyl} difluoromëthylthio-to-2 ethyl benzene-carboximidate

[577]

N-NC - (tetrafluoro-2, 3, 4, 5 phenyl) - carbamoy 11 fluoro 2 benzêne-to-carboxiraidate ethyl

[578]

N-NC- (tetrafluoro-2, 3, 4, 5 phenyl) - carbomoyl] difluoro 2.4 ethyl benzene-carboximidate

[579]

N-NC - (tetrafluoro-2, 3, 4, 5 phenyl) - carbomoyl] dichloride 2.4 benzêne-to-carboximidate ethyl

[580]

N-NC - (tetrafluoro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[581]

N-NC - (tetrafluoro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 2 fluoro 5 ethyl benzene-carboximidate

[582]

N-NC - (tetrafluoro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 4 fluoro 2 ethyl benzene-carboximidate

[583]

N-NC - (dichloro 2.4 difluoromethyl-3 trifluoromëthyl-to-5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[584]

N-NC - (dichloro 2.4 difluoromëthyl-to-3 trifluoromethyl-5 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[585]

N-NC - (dichloro 2.4 difluoromethyl-3 trifluoromethyl-5 phenyl) - carbamoy1D platinic 2 fluoro 6 ethyl benzene-carboximidate

[586]

N-NC - (dichloro 2.4 difluoromethyl-3 trifluorornéthy1-to-5 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[587]

N-NC - (difluoromêthoxy-to-4 trichloro 2, 3, 5 phenyl) - difluoro 2.6 carbamoy 13 ethyl benzene-carboximidate

[588]

N-NC - (chlorodifluorométhoxy-to-4 trichloro 2, 3, 5 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[589]

N-NC - (trichloro 2, 3, 5 trifluoromethoxy-to-4 phenyl) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[590]

N-NC - ((bromo 2 trifluoromethyl 1, 1, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[591]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[592]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[593]

N-n-[ - ((chloro 2 trifluoromethyl 1, 1, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[594]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[595]

N-R4II - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 trichloro 2, 3, 5) - dichloro 2.4 carbamoy 13 ethyl benzene-carboximidate

[596]

N-cn - ((tëtrafluoro and 1, 1, 2, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[597]

N-NC - ((tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[598]

N-NC - ((tetrafluoro-1, 1, 2, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[599]

N-£N - {(tetrafluoro-1, 1, 2, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbamoil.] platinic 2 fluoro 4 ethyl benzene-carboximidate

[600]

N-NC - ((tetrafluoro-1, 1, 2, 2 êthoxy) phenyl -4 trichloro 2, 3, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[601]

N-£N - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxÿ) phenyl -4 trichloro 2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[602]

N-NC - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) phenyl -4 trichloro 2, 3, 5) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[603]

N-NC - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) phenyl -4 trichloro 2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[604]

The n - n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 trichloro 2, 3, 5 phenyl) carbomoyl - chlorophenyl 2 fluoro 4 ethyl benzene-carboximidate

[605]

N-NC - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) phenyl -4 trichloro 2, 3, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[606]

N-NC - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[607]

N-cc.n - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[608]

N-qii - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 4 fluorocarbon 2. ethyl benzene-carboximidate

[609]

N-Lnis - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[610]

N-NC - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] chloro 2 fluoro 4 ethyl benzene-carboximidate

[611]

- 37 - 07 821 N-NC - (phënyltëtrachloro-a 2, 3, 4, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[612]

N-NC - (tetrachloro-2, 3, 4, 5 phenyl) - carbomoyl] dichloride 2.6 ethyl benzene-carboximidate

[613]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ethoxy) phenyl -4 trimethyl-2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[614]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 ëthoxy) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[615]

N-NC - ((chloro 2 trifluoromethyl 1, 1, 2 êthoxy) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[616]

N-NC - ((tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4 trimethyl-2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[617]

N-n-[ - ((tetrafluoro-1, 1, 2, 2 ethoxy) phenyl -4 trimethyl-2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[618]

N-NC - ((tetrafluoro-1j1, 2.2 êthoxy) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[619]

N-£n - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[620]

N-NC - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[621]

N-NC - ((hexafluoroantimonic 1, 1, 2, 3, 3, 3 propoxyl) -4 phenyl trimethyl-2, 3, 5) - carbomoyl] dichloride 2.4 ethyl benzene-carboximidate

[622]

N-NC - ((dichloride 1.2 éthényloxy) -4 trimethyl-2, 3, 5 phenyl) carbomoyl] difluoro 2.6 ethyl benzene-carboximidate

[623]

N-NC - (têtrafluoro-a 2, 3, 5, 6 phenyl) - carbomoyl] fluoro 2 ethyl benzene-carboximidate

[624]

N-NC - (tetrafluoro-2, 3, 5, 6 phënyl) - carbomoyl] chloro 2 ethyl benzene-carboximidate

[625]

N-NC - (tetrafluoro-2, 3, 5, 6 phenyl) - carbomoyl] chloro 2 fluoro 6 ethyl benzene-carboximidate

[626]

N-cc.n - (tetrafluoro-2, 3, 5, 6 phenyl) - carbomoyl] dimethoxy-2.6 ethyl benzene-carboximidate

[627]

N-Lnis - (pentafluorophênyl) - carbomoyl] fluoro 2 benzêne-to-carboximidate ethyl

[628]

N-NC - (pentafluorophênyl) - carbomoyl] chloro 2 fluoro 6 and ethyl benzene-carboximidate

[629]

The Ν - ζ Ν - carbamoil! (pentafluorophënyl) - dichloride 2.6 benzèneearboximidate ethyl,

[630]

The present invention also relates to methods for preparing compounds of formula I, methods according to which:

[631]

a) reacting acid esters arêne-to-carboximidiques

[632]

or arene-thiocarboximidiquessubstitués corresponding to formula II: - R.

[633]

[634]

wherein R ^ to Rgrams and X have the meanings that were given above under formula I, with compounds of any of formulas III and IV 9.ï

[635]

[636]

wherein Rgrams to R ^ and γ have the meanings that were data about the formula I and Zj represents a halogen other than a removable, for example an alkoxy radical in c ^ - ^ c-or a phenoxy radical, which may be halogenated, or an imidazolyl or triazolylq or

[637]

b) reacted ester derivatives acidesarëne - {thiourea) carbodiimide ximidiquessubstituésrépondant of formula V:

[638]

[639]

wherein RG of Rj,

[640]

X and Y have the meanings given for formula I, and^2 has the meaning of and may further be a halogen, with substituted anilines of formula VI:

[641]

[642]

(VI)

[643]

wherein Rg confectioneries Rjq have the meanings given for the formula I, or

[644]

c) are reacted anthropodicidal-a 1, 3, 5 substituted according to formula VII:

[645]

[646]

(VII)

[647]

wherein the RJ to RlOQ and: Y have the meanings given for formula I, with or substituted thiolic hydroxylic compounds corresponding to one of the formulas VIII and IX:

[648]

R-OH-^R12SHUSH

[649]

(VIII) (ÎX)

[650]

wherein R ^ and have the meanings given for formula I in confectioneries.

[651]

Esters (alkylthio) - arene carboximidiques. of formula II which are to serve as initial body in the preparation process has) are novel in part and they can be prepared by methods described in the literature,

[652]

for example ·.

[653]

1. by addition, catalyzed by an acid or base, of compounds (VIII-) or (IX.) on substituted nitriles of the formula (X-):

[654]

[655]

(S)

[656]

wherein to R5 have the meanings previously data (see R. the Rogers, mal. Rev. (51, 179 (1961));

[657]

2. acid esters by transesterification (alkylthio) - benzene (ll) carboximidiques, body easily accessible, with compounds (VIII-) or (IX.), compounds wherein R1 to R ^, R.lT. and Rl2 have the meanings previously data (see R.J. Kauffmann, dermatitis. Mal. Share. 4J5, 1744 (1923));

[658]

3. by alkylation to oxygen (or sulfur) amide (or thoiamide) substituted confectioneries formula (IX) :

[659]

[660]

THE NH, (IX)

[661]

wherein the RJ to R5 and Y have the meanings previously data (see m Matsui, military should take. Mal. Abstract This 98, 695 (1910) propynoic. and H, J prakt. Mal. 154, 154 (1940)).

[662]

The compounds (II) and (VI) to be used as initial body in the preparation process has) are known or can be prepared by methods including piggybacked on methods described in the literature (see Houben-to-Weyl-, MECT VIII., 1952, Houben-to-bulk Weyl, 4 th MECT, 1983).

[663]

acidœ arene derivatives (alkylthio) - substituted carboximidiques (volts) confectioneries body for use as starting material in the process of preparation B) can be prepared in a manner known from decomposés of formula II (see Houben-to-bulk Weyl, 4 th MECT, 1983).

[664]

(IV) of anilines required for process b) are known or can be prepared by methods described in the literature (see Houben-to-Weyl-, ' MECT (1957) xx/1).

[665]

Oxadiazines and 1, 3, 5 (VIII) to be used as initial body in the method of preparation c) can be obtained by methods described in the literature (US Patent

[666]

4,150 158).

[667]

The method has) reported above, by which to make esters of n-jârylaminocarbonyJ (alkylthio) - 5.enz's thdo (Thiourea)_ carboximidiques of formula I, is carried out in the presence of a diluent or, better, without diluent. The diluents which are suitable are essentially all aprotic solvents, especially aliphatic or aromatic hydrocarbons optionally halogenated, such as pentane, hexane, 1 '-heptane, cyclohexane, petroleum ether, gasoline, petroleum benzine, benzene, toluene, xylenes, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, the chlorobenzêne and 1 'o-dichloro benzêne, ethers, such as diethyl ether, dibutyl oxide, dimethyl ether of 1 'ôthylène glycol, ether dimêthyli -' that diethylene glycol, tetrahydrofuran and dioxane, ketones, such as acetone, methyl ëthyl-ketone, the mëthyl-to-isopropylcëtone and the mëthyl isobutyl cëtone, esters, such as methyl acetate and ethyl acetate, nitriles, such as acëtonitrile and the propionitrile, amides such as dimëthylformamide, the diméthylacëtamide and n-mêthylpyrrolidone, as well as dimethyl sulfoxide, the tétraméthylêne sulfone and the hexamëthylphosphorotriamide.

[668]

The reaction temperature is generally between -10 et + 150 °c, preferably between + 10 and 105 °c.

[669]

The initial body are ordinarily involved in equimolar amounts. It is however possible to use an excess of one or the other of the reactive components.

[670]

Reacting the process b) is preferably carried out in a diluent. All organic solvents neutral, non-nucleophilic, are suitable but those are preferred which have been mentioned about the method has).

[671]

The reaction temperature is generally between -10 et + 140 °c, preferably between + 10 et + 80 °c.

[672]

The initial body are ordinarily involved, as in the method has), in equimolar amounts. An excess of one or the other of the reactive components is still possible.

[673]

In preparing the compounds of formula I by the process c) it is good, in the reaction of the compounds (VIII) with components (VIII.), to involve an excess thereof.

[674]

In the reaction of compound (VIII) with compounds (IX.) is ordinarily involved equimolar amounts of components and operation is carried out advantageously in a diluent, more particularly dansl ' ofactuating those mentioned confectioneries about the method has).

[675]

The reaction temperature is usually from about + 20 et + 150 °c, preferably between + 50 et + 100 °c.

[676]

The isolation and, optionally, purification of the compounds of formula I are performed by methods generally couraites, for example by evaporation of the solvent (optionally under reduced pressure), then recrystallization of the residue or by chromatography.

[677]

The compounds (I-) are then obtained in the form of isomers or in the form of mixtures e/z. E/z mixtures can be resolved by physical methods known, inter alia by fractional crystallization. The two isomers were biologiquements active and therefore they are both covered by the present invention.

[678]

The compounds of formula I dissolve well in most organic solvents.

[679]

The active compounds, which are well tolerated by plants and which are little toxic confectioneries homëother MES-feasible, are well suited for combating pests organic catalyst, especially against insects, arachnids and nematodes, in particular insects, who were business ·℮η agricultural, forestry, in the protection of stored products and materials and in the hygiene field. They are effective against species to normal sensitivity and species resistant as well as against all development stages or only against certain stages. Among the above-mentioned pests include of for example:

[680]

- in the order of the Isopoda: e.g. Oniscus, Armadillidium vulgare and, Porcellio dilatatus scaber;

[681]

- in the order of the Diplopoda: Blaniulusguttulatus;

[682]

- in the order of the Chilopoda: Geophiluscarpophagus, willwill scutigera spec.;

[683]

- in the order of the Symphyla: Scutigerellaimmaculata;

[684]

- in the order of the Thysanura: Lepisma saccharin;

[685]

in the order of the Collembola -: Onychiurusarmatus;

[686]

- in Orthoptera: Blatta Blatta orientalis, Periplaneta americana was, geographica maderae, Blatella, purchased musculus, Gryllotalpaspp., Locusta migratoria have migratorioides, either Melanoplus differentialis, Schistocerca;

[687]

- in the order of the Dermaptera: Forficula Radix auricularia;

[688]

- in order isoptera: Reticulitermesspp.;

[689]

in the order of the Anoplura -: Phylloera stoma, phemphigus spp., Pediculus corporis be, Haematopinusspp., Linognathusspp.;

[690]

- in the order Mallophaga: Trichodectesspp., Damolineaspp. - in the order Thysanoptera: Hercinothripsfemoralis, as thrips tabaci;

[691]

- in the order of hétëroptères: Eurygasterspp., Dysdercusintermédius, Piesma lorica, Cimexlectularius, Rhodnius prolixus that, triatoma genus spp.;

[692]

- in the order Homoptera: brassicas whitefly, Bemisia, orTrialeurodes vaporariorum, USDA APHIS gossypii, Brevicoryne brassicas, Cryptomysusribis, Doralisfabae, Doralis Shoene, Eriosema lanigerum, Hyalopterusarundinis, Macrosiphiumavenae, mysusspp., Phorodonhumuli, padi, Empoascaspp., Euscelusbilobatus, Nephotettixcincticeps, Lecaniumcorni, Saissetia Dacus, Laodelphaxstrjatellus, Nilaparvatalugens, Aonidiellaauroantii, Aspidiotushederae, Pseudococcusspp., Psyllaspp.;

[693]

- in the order Lepidoptera: willwill pectinophora SOG ' sypiella, Bupaluspiniarius, Cheimatobia Operpthera brumata, Lithocolletisblancardella, Hyponomeutapadella, Plutellamaculipennis, Malacosomaneustria, Euproctischrysorrhoea, ectomycorrhizas spp., Bucculatrixthurberiella, Phyllocnistiscitrella, anAgrotis spp., Euxoaspp., Feltiaspp., Eariasinsulana, Boddie spp., Laphygmaexigua, Mamestra species brassicas, Panolisflammea, Prodenia willwill litura, Spodoptera littoralis spp., Trichoplusia nor, Carpocapsapomonella, ELerisspp., Chilospp., Pyrausta ECB mutates, kuehniella. Toward Galleria mellonella, Cacoeciapodana, Capuareticulana, Choristoneura fumiferana were, Clysiaambiguella, Homonamagnanima, Tortrixviridana;

[694]

- in the order Coleoptera: anobiida punctatum, Rhizoperthadominica, Bruchidiusobtectus, Acanthoscelidesobtectu ^ Hylotrupesbajulus, Agelastica RFLPs, Leptinotarsadecemlineata, Phaedoncochlearieae, aDiabrotica spp., Psylliodeschrysocephala, Epilachna frontalis, Atomariaspp., . Oryzaephilussurinamensis, Anthonomusspp., weevil Sitophilus spp., Otiorrhynchus Otiorhynchus sulcatus, cosmopolitan sordicus, Geutorrhynchusassimilis, willwill hypera postica, Dermestesspp., Trogodrma spp., Anthrenusspp., Attagenusspp., Lyctusspp., Meligethesaeneus, Ptinusspp., Niptushololeucus, Gibbiumpsylloides, Tribolium castaneum spp., molitor larvae, Agriotesspp., Conoderusspp., the Melolontha the Melolontha, Amphimallonsolstitialis, Costelytra zealandica grub;

[695]

- dansl * order Hymenoptera: sawfly spp., Hoplocampaspp., Zoogonus spp., Monomoriumpharaonis, Vespaspp.;

[696]

- in order diptera: Aedes aegypti spp., of Anopheles spp., Culex quinquefaxciatus spp., Drosophila, parasitizing Musca spp., Fanniaspp., Desvoidy erythrocephala, from Lucilia spp., Chrysomyaspp., fly Cuterebra spp., Gastrophilusspp., Hyppoboscaspp., Stomoxysspp., estrus spp., Hypodermaspp., Tabanusspp., Tanniaspp., Bibiohortulanus ., fried Oscinella, Phorbiaspp., Pegomyiahyoscyami, medflies, Dacus oleae, Tipula facility be;

[697]

- in the order of siphonaptères: Xenopsylla trispinis cheopis, Ceratophyllusspp.,

[698]

- the class Arachnida: Scorpiomaurus, Latrodectusmactans.

[699]

The invention further relates to products comprising compounds of formula I as well as formulation auxiliaries suitable *

[700]

The products according to 1' invention contain the active materials of formula I into cbsconcentrations generally between 1 and 95% by weight. The data may be displayed, for the applications, in the form of wettable powders (powders for slurries), êmulsionnables concentrates, solutions puvérisables, agents poudrageoude granules, formulations that have conventional make-ups.

[701]

Wettable powders are compositions that can be uniformly dispersed in water and which, in addition to the active material and a diluent or an inert filler, contain wetting agents, in particular the poly-ethoxylated alkylphênols, alcohols polyunsaturated fatty êthoxylés, alkane sulfonates or alkyl phenol sulfonates, and dispersants, such as lignin-suifonate sodium, the sodium salt of dinaphtyl - 2.2 'mêthane-a-disulphonic 6.6', the sodium salt of acid dibutyl naphthalene sulfonic acid or sodium salt 1 'oleyl-methyl taurine derivative.

[702]

To prepare êmulsionnables concentrates the active material is dissolved in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or else aromatics or hydrocarbons boiling above pqint confectioneries, in the presence of one or more emulsifiers. Panels will be able to be for example calcium salts of alkyl arene sulfonic acids, such as dodëcyl-to-benzêne sulfonate calcium, or nonionic emulsifiers such as products ^ polyêthoxylation fatty acid, of alkylphénols or fatty alcohols, condensation products of propylêne oxide/ethylene oxide, alkyl polyethers, fatty acid esters of sorbitan, fatty acid esters of polyoxyêthylêne-to-sorbitanspolyoxyéthylènesorbitols or esters.

[703]

The spreading agent are prepared by grinding

[704]

the active ingredient with finely divided solids, such as talc, natural clays (e.g. kaolin), bentonite, the pyrophillite or diatomaceous earth.

[705]

. Prepare can either project the active material by utilizing a nozzle on an adsorptive granulated inert material, either apply a concentrate of the active material, by means of adhesives, such as poly (vinyl alcohol) -, poly (sodium acrylate) - or mineral oils, on the surface of media, such as sand, kaolinite or granulated inert material. The actives therein prêtentpeuvent also be developed in the usual manner for the production of fertilizer granules, if desired in a mixture with fertilizers.

[706]

In their commercial formulations and in the ready to use composition and that is manufactured from such formulations the active compounds according to the invention may be mixed with other active materials, such as insecticides, attractants, sterilants, acaricides, of nëmaticides, fungicides, growth substances or herbicides. Among insecticides include e.g. phœphoriques esters, carbamates, esters of acidescarboxylique ^ chlorinated hydrocarbons, to substituted phenyl ureas, once synthesized substances by microorganisms andc.

[707]

The content of active substance compositions ready

[708]

to the application that have been prepared from the commercial formulations can confectioneries vary in extended intervals, for example between 0.0000001 weight and 100%, preferably between 0.00001 and 1% by weight.

[709]

The application mode will be adapted to the application form as usual.

[710]

The active compounds according to 1' are also useful for combating ectoparasites or endoparasites, insect ectoparasite. preferably, in the field of veterinary medicine or in the field of maintenance of animals.

[711]

The active compounds according to the invention are then applied in a known manner, such as by the oral route in the form, for example, tablets, capsules, drinks or granules, by dermal route, for example by immersion, spraying, watering (for on earth and spot on) and dusting, as well as the parenteral route, e.g. via injection.

[712]

The novel compounds of formula I which are the subject of the invention may therefore be applied, and this is particularly advantageous, in the breeding of animals, such as cattle, the ovidés, . swine and poultry, such as chickens, geese and so on in one embodiment of the invention which is particularly interesting the novel compounds are administered to the animals by the oral route, optionally in suitable formulations (see above) and optionally with the drinking water or feed. The excretion in the feces is done very effectively in this manner very simply inhibit development of insects in the excreta of animals.

[713]

The doses and the formulations which are suitable in each case depend on the type of livestock and their stage of development, as well as degree of illness by insects: they are will determine without difficulty by the usual methods. The novel compounds can be used, in bovidae, in doses ranging between 0.01 and example 1 mg per kilogram body weight.

[714]

The following examples illustrate the invention.

A. exemplary related formulations

[715]

a) preparing a dusting agent by mixing:

[716]

10 parts by weight of active material and

[717]

90 parts by weight of talc, as bulking agent,

[718]

and is ground in a mill all spider.

[719]

b) preparing a wettable powder which is easily dispersed in water by mixing:

[720]

25 parts by weight of active material,

[721]

65 parts by weight of kaolin-containing quartz, 10 parts by weight lignin sulfonate potassium-and 1 part by weight of the sodium salt of olëoylméthyltaurine, as wetting agents and dispersants,

[722]

and is ground in a mill all the confectioneries toothed rings.

[723]

c) a dispersion is concentrated which is easily dispersed in water by mixing:

[724]

20 parts by weight of active material with

[725]

6 parts by weight of a product of an alkylphenol polyethoxylation (as Triton X 207),

[726]

3 parts by weight of a product polyethoxylation of 1' isotridecanol (to 8 ethylene-oxy-patterns) and 71 parts by weight of a paraffinic mineral oil (whose boiling range will for example about 255 more than 377 °c)

[727]

and is ground in a ball mill any friction to a fineness less than 5Jxm.

[728]

d) can be prepared from a concentrate êmulsionnable confectioneries:

[729]

15 parts by weight of active material,

[730]

75 parts by weight of cyclohexanone, as solvent and 10 parts by weight of a poly ethoxylated nonylphënol

[731]

(to 10 éthylêne tetramethyleneoxy units), as emulsifier.

[732]

e) OH-granules prepared from 2 to 15 confectioneries parts by weight of active material and an inert carrier material pourgralés, as 1' of attapulgite, pumice granules and/or quartz sand.

[733]

The O say N.R1R2R3R4R5R6R7R8R9Ri0XYw - °C E/z Malange
1FHHHPPABOUT H. HH093 - 95
2osh5HHHOSH ^PABOUT HHH°C2 hr50H3 - H5
3PHHHHof OC2 hr5ABOUT HHHof OC2 hr5077
4HHHHHHas OCP2 the CHP2 HR••HHof OC2 hr5062
5PHHHPHa ro2HHHof OC2 hr50: 128
6PHHHLCHa ro2HHH. of OC2 hr50110
7PHHHHHmC5HHH00 ρΗς094
fS3
8PHHHHHcooch5HHH0C2H50100
9PHHHHHthe CHP2HHHof OC2 hr50102
10PHHHHHMC5 hrHH0C2H50' 120; 1,

[734]

B.. Chemical examples

[735]

G. №R1R2R3R4•R.5R6R7R8R9R10XYP-e/z•°C mixture
11PHHHHHHPHHOf OC Hçj ^078 - 80
1, 2HHHHHHHLCHHof OC2 hr50128•
12HHHHHHHLCHHosh2 =HC0114
UPHHHHR;HHLCHH0C 2H 50130 - 132
15F. H■HRHHHR■HOCHPgHHOC2H50109
1601HHHHHHochf2HHof OC2 hr5080
17' WHHHTHE P 'HHOCHPgHHof OC2H5089
18FHHHLC.HHochf2HH0c2 hr5088
19LCHHHLCHH0CHF2HHof OC2 hr5095
20PHHHHHH0CC1P2HHof OC2 hr5093 - 95 5

[736]

οο Ν 3

[737]

The ex. No..R1R2R3R4R5R6R7R8R9R10XF * c e/z mixture therein
21HR.HHR.HHHH0CF3HHof OC2 hr5085
22PHHHHHH0CF5HHosh50125 - 127
23PHHHHHHocf3•HRHof OC2 hr5097 - 99
24PHHHHHHOCF, 5.HHDEGREES (HM 2)2 HM3084
25PHHHHHHPDO ^HHthe O (CH22 )5 hM3, 0i-I-•- 105 IU
26PHHHHHHOCF, 5HHthe O (CH22 )5 hM3, 0the I 69 - 71
27PHHHHHHPDO, 3HH- °KD0130 - 132
28HPHHHHHocf3HHof OC2 hr5the O -56
29LCHHHHHHocf3HHof OC2 hr5086 - 87
50HHLCHHHHPDO, 3HHof OC2 hr50110^

[738]

COEXTRUDED

[739]

No..R1R2R3R4R5R5R7H8R9R10XE/z mixture therein
31THE X.HHHHHH0CF3HHof OC2H50115
32PHFAHRENHEIT.HHHH0 CP5HHof OC2H5091
33PHHHPHH0 CP3HHof OC2 hr5090 - 93
34PHHHPHHOCF,HHthe O (CH22 )5 hM3071
35PHLCHHHHOCF, ... 3HHof OC2 hr5099 ' a
36' WHHLCHR.HH0 CP3HHof OC2 hr50!113
37PHHHLCHH0 CP3HHof OC2 hr5088
38'LCHPHHHH0 CP3HHOf OC■2 hr5079
39LCHR.HPHHR•Hocf3HHof OC2 hr5092 CDS
40LCHLCHHHH0 CP3HH0C2 hr509100 a ro

[740]

The ex.( P-•I R-NO grams1R2R3R4R5R5R7H8R9R10 X-mixture

[741]

Ex.eC R-NO1R2R3R4R5RSR7R8R9R10 X-e/z mixture

[742]

No..R1R2R3R4R5RSR7R8R9R10XYE/z mixture
41LCH- HRLCKRHocf3 .HHof OC2 hr5 '0HQ IN
42LCHHHLCHHocf3HHR.of OC2 hr5099 - 102
45FFFFFHHocf3HHof OC2 hr50123 - 125
44LCHHHOSH, 5HHocf3HHof OC2 hr50130
45FHHno.2HHHocf3HHof OC2 hr50 *102 - 105 Û
46LCHHno.2HHHocf3HH0C2H50i-150
47HM - ^ in EdmontonHHHHHH0CF3HHof OC2 hr5094 - 96
48cHF is2 the O -HHHHHHocf3HHof OC2 hr5087
49HHfS3 the O -HHHHocf3HHof OC2 hr5097
50HfS3 the O -HHHHHocf3HHof OC2H5082 of OC<R.

[743]

The HO.R1R2R3R4R5R6R7R8R9R10XYE/z mixture
51HM - ^ THE OHHHTHE H 'HHocf3 .HH0C 2H 50104
52HSKC HR3 mC2 the O -HHHH0CF3HHof OC2 hr50118
55the CHP2s_HHHHHHocf3HHof OC2 hr5092
5' 4Hno.2HmC3HHH0CF5HHof OC2 hr50153
550.5n3HTHE H 'HTHE H 'HHocf3HHof OC2 hr50i-U-Æ>! 95 - 98.
56HmC5HHHHH°CP5HHosh3 ,01,160
57hM3HKHHHH0 CP3HH0C2R50, 113
58HHR■HHHHH0 CP2 THE CHP2HTHE II0CH2QSH0101 - 103
59HHHHHHHas OCP2 the CHP2HH0CH2 MC50157 - 139 n-
60PHHHHHHas OCP2 the CHP2HHof OC2 hr50116. k-pp:

[744]

The ex.. F * c an HO. R1R2R3R4R5R6R7R8R9R10 X-•e/z mixture

[745]

No..R1R2R3R4RSR6R7R8R9R10XYMixture E/Z
61FKHR•HTHE H 'HH0CF2CHC12HHof OC2H50114 - 116
62FAHRENHEIT.HHHHHH- 0C HM=L-LC/LCHHof OC2H5. 0106 - 108
63FHHHFHHthe FCB -3HHof OC2 hr5096 - 98
64FHHHHHH- SCFgCHCiFHHof OC2 hr5089 i-
65FHHHFHHOF S0 -2 FS5HHof OC2 hr50112W. the I
66FHHHHR.H.Hno.2HHof OC2 hr50155
67LCHHH' HRHHThe O ERHHof OC2 hr50161
68FH- HRHFHHno.2HHof OC2 hr50165
69FHHHLCH- HR5 ¾ OF O CM.HHof OC2 hr50160 - 162 cDs
70LCHHHLCHH5 ¾ OF O CM.HHof OC2 hr50Coextruded 170, ο

[746]

The ex. F * c R-NO1R2R3R4RSR6R7R8R9R10 X-mixture E/Z

[747]

The ex.

[748]

No..R1R2R3R4R5R6R7R8R9R10XYE/z mixture
71PHHHTHE H 'HHMC3HHof OC2H50131
72PHHHLCHHfS3HHOF OC2H50115
73LCHHHLCHHMC3HHof OC2H50122 - 125
74PHHHHHTHE C - (FS3 )2 0:00 HrHof OC2 hr50oil
75PHHHPHHthe c - (FS3 )2 oH-hrH0C2H50i-oil
76PHHHHHHC00CH - H 3THE II 'OCgH ^0165
77W.HHHHHHC2H5 . HHof OC2 hr30116
78PHHHHH' HRthe c - (CH23 )3 hrHof OC2 hr501, 65
79PHHHήHHLC hrH°02 hr5O134
; MC
80PHHHHHHocf3HHthe SCH3 ,0134 E

[749]

a ro

[750]

Receive

[751]

G. üo.R1R2R3R4R5R6R7R8R9R10XP * c e/z mixture therein
81LCH- HRHTHE H 'HHocf3HHTHE SCH30131 - 132.
82LCHHHHHHfS3HHTHE SCH30159 - 160
83PHHHHLCLCHHHof OC2 hr50105
84PTHE H 'HHTHE H 'LChM3HHH0C2 hr50110
85FHHHHPHPHH0C2H 50i-73 u1
86PHPHHPHPHH0C 2:0050! 71
37PHLCHHPHPH:Hof OC2 hr50105 - 106
88PHHLCHPHPHHof OC2 hr50103
89PHHHLCPHPHH0C 2H 5095
90LCHPHHPHPHHof OC2 hr5' 097 - 99 the K

[752]

The ex. No..R1R2R3R4R5R6R7R8R9R10XYPI c. mixture
91LCHHPHFHPHHof OC2H50101
92PHHR•HHLCHLCHHof OC2 hr50136 - 138
95PHHHHmC3HLCHHof OC2 hr50120
94PHHHHLCH- CH2 (CH25)2HHof OC2 hr5069
95PHHHP0 CP2CHC1P hr0 CP2CHC1P hrHof OC2 hr50oil
96PHHHHLCHHFS, 5H0C2H 50121
97hM3 the OHHHhM5 the OPHHPH0C 2H 50104
98hM5 the OHHHhM3 the OPHHHPof OC2 hr50140
. 99hM5 the OHHTHE H 'THE O ^ HCLCHHHLCof OC2 hr50200
100hM3 the OHHHTHE O ^ HCthis3HHHhM3of OC2H50oiled

[753]

VITALITY AND.R1R2R3THE R *R5R6R7R8R9R10XYE/z mixture
101THE O ^ HCHHR•HTHE O ^ HCHM ^THE IIHHC.2 hr5of OC2 hr50oil
102LCHHHHHLCPHHof OC2 hr5095
105PHHHKHLCPHHof OC2 hr5088
104PHHHHHN02PHHof OC2 hr50145 - 147
105PHHHPHP- c.' OHjHH0C2 The HP;0i-u1 VOs oil I
1, 06PHHHHH. the OLCHHOCgHçj0150
107LCHHHHHLC0CF2CHC1FKHof OC2 hr50oil
108PHHHHHLCOCPgCHCIPHHof OC2 hr50oil
109PHHHPHLC0CF2CHC1FHH0C 2H 50THE CD 78 COEXTRUDED
110FHHHLCHLCocf2chcifHHof OC2 hr50a ro - 901 the K

[754]

The ex. F. °C

[755]

THE N<>.R1R2R3R4R5R6R7R8R9 'R10XYE/z mixture
111LCHHHLCHLC0CF2CHC1FHHof OC2 hr5070
112PHHHHHas OCP2chcipLCHHOCgHcj0128 - 129
115LCHHHHHOCPgCHCIPLCHHof OC2 hr50110 - 111
1 ΗPHHHPHocf2chcifLCHHof OC2 hr50117
115PHHHLCHOCPgCHCIPLCHH0C2 THE II50123 A J,
116PHHHHHocf2 cHF is2LCHH0C 2H 50150 - 132'
117PHHHHHLCC00C (HM5 )5HHof OC2 hr50oil
118PH■HRHHHLChM3HHof OC2 hr50105
119PHHHHHLCLCHH°C2 the K50. 96
120HPHKHHLCLCHH0C2H 50105 coextruded to verbs

[756]

The ex. W '* MOLECULAR<>. R1R2R3R4R5R6R7R8R9 ' R.10 X-e/z mixture

[757]

V

[758]

The n-O.R1R2R3R4R5R6R7R8R9R10XYE/z mixture
121THE I,HHR•HHHLCLCHHthe O ' C.2 hr50109
122LCHHno.2HR.HD.LCHHof OC2 hr50140
123LCHLCHHHLCLCHHof OC2 hr50120
124LCHHLCHHLCLCHHof OC2 hr50124
125PPPPPHLCLCHEof OC2 hr50105 *1&
126HCP3OHHHHLCLCHHof OC2 hr50'85'
127HHCP3OHHHD.LCHHof OC2 hr5085
128hM5 the OHHHHHLCLCHHof OC2 hr50143
129Hno.2HfS5HHLCC1HHCE-PEÇ0139 - 141
1 · 30mC5HHHHHLCLCHHOF OC2H50IC? 155 coextruded WS

[759]

•G._ F.;: ·℮

[760]

F., -. r-NO * C.the LR2R3R4RSR6R7R8R9R10 X-mixture

[761]

No..Rthe LR2R3R4RSR6R7R8R9R10XthereinE/z mixture
131ΗfS3HHHTHE IILCLCHHosh3 '0118
132FHHR.HFHochf2OCHFgHHof OC2H50oil
133FHHHFHhM3THE O -HH0C 2H 50oil
134FHHHHHhM3hM3HHof OC2 hr5089.
135LCHHHHHfS5LCHHthe SCH3the P96 - 99 SECONDS
136FHHHHH01LCHHTHE SCH-TO-30125 i-
137LCHHHHHrOLCHHthe SCH30. 125
133FHHHHH01HLCHof OC2 hr5098
139FHHHHHfS3HfS3Hof OC2H501 - 40.
140FHHHHHCH 3HhM3Hof OC2 hr5077 - 80 CDS ^ COEXTRUDED.

[762]

No..R1R2R3R4R5R6R7R8R9R10XYMixtureE/2
H1PHHR.HHHC2HÇSO2- HRthe c?3Hof OC2 hr50102
142PHHHHPHPLCTHE IIof OC2 hr5085
143LCHHHH. PHPLCHof OC2 hr50.55
144PHHHPPHPLCHof OC2 hr50120■
145PHH' HRLCPHPLCH0C 2H 50601 "therein" U-)
146LCHHHLCPHPLCHof OC2 hr5092J
147PHHHHLCHHM, 3BrrHof OC2 hr50.210
148PHH•HRHLCHLCLCHof OC2 hr50140
1, 49PHHHPHLC0CF2CHC1FhM3Hof OC2 hr50128
150PHHHTHE H 'HfS3LCCP3Hof OC2 hr50164THE O ' - O-PP

[763]

The ex. V-VBE1 " R-no. 10 C.1R2R3R4R5R6R7R8R9R10 X-mixture

[764]

The ex. No..R1R2R3R4R5R6R7R8R9' R.10XYThe Fy# C. mixture E/Z
151PHHHPHLCochf2 LCH0C2H 50oil
152PHHR•HHHLCocf2chcif LCHof OC2H50' 128
153LChr;HHHHLC0 CP2CHC1P LCHof OC2 hr50103 - 105
154PhrHHPHLC0 CP2CHC1P LCH07 o-IR-VBE1(O-Λ.
155PHHHLCHLC0 CP2CHC1P LCHof OC2 hr5the O '123 - 124 gm.
156LCHHHLCHLC0 CP2CHC1P LCHof OC2 hr5.0110 - 112'
157PHHHHHLCOCPgCHBrP LCHof OC2H50121 - 124
158LC•HRHHHHLCOCPgCHBrP LCH°C2hr 5096
159PHHHPHLCOCPgCHBrP LCHof OC2 hr50the O-O 0, 1
the O.
160PHHHLCHLCAS OCP2CHBrP LCHof OC2 hr50■118 - 120 COEXTRUDED

[765]

eR g. Y-R-NO•* C.1R2R3R1 THE R *5R6R7R8R9R10 X-e/2 mixture

[766]

No..R1R2R3R1 *R5R6R7R8R9R10XYE/2 mixture
161LCHTHE H 'HLCHLC0CF2CHBrPLCHof OC2 hr5 '0101 - 205
162PHHHHHLCocf2 guanylyltransferase2LCH0CH30110 - 115
163PHHHHHLCocf2 cHF is2LCHof OC2 hr50' 123 - 124 -
1, 64PHHno.2HHLCas OCP2 the CHP2LCHof OC2 hr50113
165LCHHHHHLCocf2 cHF is2LCH0VI ' 124 - 125 * U-
166HHLCHHHLCocf2 cHF is2LCHof OC2 hr50155
167PHHHPHLCocf2 cHF is2LCHof OC2H50120 - 121;
168PHLCHHHLCocf2 cHF is2LCHof OC2 hr50142 VOLTS.
169PHHLCHHLCocf2 cHF is2LCHof OC2 hr50149
170PHHHIC. HLC0 CP2 BFG2LCHof OC2H50115 - 116 2

[767]

pp ER F., ;. * C.

[768]

o-tee!R1R2R3R4R5R6R7R8R9R10XE/z mixture therein
171LC•HFHHHLCocf2 cHF is2LCHof OC2 hr50132
172LCHHR•HhM3 the OHLCocf2 cHF is2LCHof OC2 hr50138
173LCHLCHHHLCocf2 cHF is2LCHof OC2 hr50135
174iCHHH•LCHLC0CF2 CHF ISthe OLCHof OC2 hr50111 - 112
175HM3 0HR.HHhM3 the OHLCocf2 cHF is2LCHof OC2 hr50104•J. has
176HM5 S02 0 -HHHHHLCocf2 cHF is2LCHof OC2H50i-oil
177cHF is2 - eHHHHHLCocf2 cHF is2LCHof OC2 hr5091
178hM3HHHHHLCocf2 cHF is2LCHof OC2 hr50138•
179FHHHHHLCocf2 cHF is2LCH0 (hM2 )2 hM30118
180FHHHHHLC0CF2 CHF IS2LCH0 (HM2 )3 HM30■109 C. therein the ex

[769]

Λ

[770]

No..R1R2R3R4R5R6R7R8R9R10XYMixture:
181FHHHHHLCocf2 cHF is2 LCHthe O (CH22 )5 hM5082 - 83
182FHHHHHLC0CF2 CHF IS2 LCH-00151 - 135
183FHHHHHLC0 CP2CHFCP5 LCHOCgHçj0105
184LCHHHHHLC0CF2CHFCF5 LCHof OC2 hr50103 - 105
185FHHHPHLC0CF2CHFCF5 LCHof OC2 hr5094 - 97:
186FHHHLCHLC0CF2CHFCF5 LCHCE-pHtj0103
187LCHHHLCHLC0CF2CHFCF5 LCHof OC2 hr5090 - 91
188FHHHFHLC0CH2 FS5 LCHof OC2 o ^0101
189FHHHFHLC0CH 2 - (o-)"C1 LCHof OC2H50143 - 145
190FHHHFHLCQ-a-c=ch-LCH0Cthe O HR - ' -0oil

[771]

The ex. F.' R-NO * C.1R2R3R4R5R6R7R8R9R10 X-mixture:

[772]

ItWITH DEGREES LC pp•ER LC

[773]

G. sec. No..R1R2R3R4R5R5R7R8R9R10X' THEREINF.; e/e mixture * C.
191RHHHFHLCschf2LCHof OC2 hr30oil
192FHTHE H 'HHHLCTHE O -LCH0C 2H 5•093 - 95'
193FHHHFHLCC00 (HM2 )6 HM3LCHof OC2 hr50oil.
194LCHHR.HHHR■hM3ocf2 cHF is2hM3Hof OC2 hr50111 - 112.
195FHHHHR•' F.LCFLCH°02 hr50i-the £125 - 126
196LCHHHHFLCFLCH0C 2H 50i-113 - 114
197FHHHLCFLCFAHRENHEIT.LCHof OC2 hr5098 - 99
.198LCHHHLCFLCFLCHof OC2 hr50115 - 116
199FHHR■HHFFFFthe H 'pp2 hr50127 - 128
200FHHHHLCCHF IS2 LCfS3Hof OC2 hr50THE CD1 "8 Œ10

[774]

G. · · Ρ· * NO C. R.1R2R3R4R5R6R7R8R9 ' R.10 /Mixture into the X

[775]

No..R1R2R3R4R5R6R7R8R9 'R10XI/mixed in
201LCHHR.HHLCthe CHP2LCfS3Hof OC2 hr50103
202PHHHLCLCcHF is2LCfS5Hof OC2 hr5081 - 86
203LCHHHLCLCCHF IS2LCfS3Hof OC2 hr50124
204LCHHHHLCLCLCLCH00 2hr 50140
205PH. HHHLCLCLCLCHof OC2 hr50147
206PHHHLCLCLCLCLCHof OC2 hr50165
207LC' HRHHLCLCLCLCLC■Hof OC2 hr50172
208PHHHP°h3HM50CF2 CHF IS25&C.H0C2 hr50oil
209PHHHHPPHPTHE P '°C2 hr50161
210LCHHHHPPHPP00 2hr 50■150

[776]

The ex. The HO.R1R2R3R1 *R5R6R7R8R9R10XTHERE]Ρ ·℮ e/z mixture
211FΗΗΗLCFFΗΡΡ00 2H 50125 - 128
212FΗΗ -ΗΗFFΡΡΡOF OC 2H 50122
213LCΗΗΗΗFFΡΡΡ°o2 hr50110
214FΗΗΗLCFΡΡΡΡ°C2 hr50143
215LCΗΗΗLCFΡΡΡΡ°o2 hr50150,

[777]

ο-I

[778]

Coextruded ό O-lo

[779]

The aforementioned compounds can be prepared by any of the methods shown below.

[780]

Each method is illustrated using an example of the table.

[781]

Method has) - Preparation of the compound of the example no.14 stirred 20 °c during 4 hours 8.36 (50 mmole) g-fluoro-2 benzene-carboximidate 6.14 g of ethyl isocyanate (50 mmole) of P-chloro-phenyl. Then added 20 ml of n-hexane, solid material is separated by dewatering, washed with n-hexane and dried.

[782]

Amount collected: 14.3 grams (yield: 89%) melting point: 130 and 132 degrees Celsius.

[783]

Process b) - Preparation of the compound of the example no.71 has 9.19 grams (40 mmole) of n - (chlorocarbonyl) fluoro 2 benzene-carboximidate and 4.05 g of ethyl (40 mmole) of triethylamine in 50 ml of anhydrous methylene chloride

[784]

added dropwise 6.45 grams (40 mmole) of P trifluoro-methyl-aniline and stirred for 6 hours at ambient temperature. The organic phase is washed with water, dried on MgS04 , it is concentrated by evaporation and the residue is recrystallized in n-hexanè.

[785]

Amount collected: 12.0 grams (yield: 85%) melting point: 131 °c.

[786]

Process c) - Preparation of the compound of the example no.33 is boiled under reflux for 4 hours 11.95 grams

[787]

(30 mmole) of (difluoro 2.6 phenyl) -6 (trifluororaêthoxy-to-4 phenyl) tetrahydro-1, 2, 3, 4 -3 2:00, 4h-to-oxadiazine derivatives L, 3.5 dione 2.4 and 100 mg of sodium methylate in 50 ml of anhydrous ethanol, cooled to room temperature, diluted with water, separated by dewatering the solid material precipitated, dried and is recrystallized in n-hexane.

[788]

Amount collected: 5 grams (yield: 43%)

[789]

Melting point: 90 and 93 degrees Celsius.

C biological examples

[790]

Such as I

[791]

Test on Spodopters

[792]

Using a sputtering apparatus is treated of larvae of the African cotton (Spodopters! littoralis, stage I-III) and petri dishes in which there is interposed a food product based on agar, by a composition comprising the active compound concentration required the confectioneries "when deposition sprayed is dry is provides the larvae on the food product based on agar"

[793]

When a desired amount of time. e ' is elapsed (stage I-III until hatching releasing the throttle) determined the fatality rate of tracks or hatching releasing the LS butterflies in %. The value 100% means that all caterpillars have been killed or that none throttle did. hatched crawlers "

[794]

In this assay found with an active-substance concentration of 0,001% our compounds. 16, 18, 20 ., 22, 23, 24, 29, 31, 33, 37, 40, 42, 71, 93, 102, 106, 107, 108, 109, 119, 123, 152, 153, 154, 155, 156, 157, 158, 159, 162, 163, 165, 167, 170, 183, 184, 185, 186, 195, 196, 197, 201 and 205 ontiune action.de 100%.

[795]

Such as II

[796]

Test parasitizing Musca

[797]

Introduced houseflies (parasitizing Musca domestica), 24 hours old, inside a chamber where there is a food product for fly which has previously been treated with a composition having an active material adapted to the -.

[798]

desired focus.

[799]

After the wanted time (of there hatching releasing fly) determined the fatality rate of larvae or hatching fly %. The value 100% means that all beetle larvae have been killed or that none fly does hatched pupae "

[800]

In this assay found with an active-substance concentration of 0.01% compounds Nos. 20, 23, 29, 33, 185, 195, 196, 197 and 215ont a level of activity of 100%.

[801]

Such as III

[802]

Test on Aedes aegypti

[803]

The Erlenmeyer flask is introduced in an aqueous composition comprising the active material to the desired concentration, and then is of larvae of the yellow fever mosquito (Aedes aegypti aegyptil), 24 hours old.

[804]

At the end of the desired time (until hatching giving imago) determined the fatality rate of larvae or hatching mosquitoes by %. The value 100% means that all beetle larvae have been killed or that none mosquito hatched.

[805]

In this assay found avecavec.une active-substance concentration of 0,001% compounds Nos. 3, 4, 9, 10, 14, 18, 20, 21, 23, 28, 29, 31, 33, 37, 40, 41, 42, 50, 51

[806]

14,18, 20, 21,23,28,29, 31, 33, 37,40,41,42, 50, 51
55,56, 58, 60,61,62,71, 72, 80, 81,82,93,103, 106,
111,114,116,119,126, 127,131,135,137,, 138, 139,142
143,144,146,153,154, 155,158,159,162,, 163, 165,167
169,170,173,179,180, 182,184,185,187,195, 196,197
and 204 haveaacting<100% of

[807]

Example VI

[808]

Test on frontalis

[809]

Using a sputtering apparatus is treated

[810]

the beetle larvae Mexican bean (frontalis varivestisL lll) by a composition containing the active material.. to a desired concentration. At the same time are immersed sheets of the kidney bean (Phaseolus vulgaris extract) in the corresponding active material solution. When deposition is applied by spraying is dry provides the larvae of the ladybug on the. bean sheets.

[811]

At the end of the desired time (L-III until hatching of the ladybug) determined the fatality rate of larvae or hatching ladybirds in %. The value 100% means that all beetle larvae have been killed or that none ladybug hatched pupae.

[812]

In this assay found with an active-substance concentration of 0.1% the compounds Nos. 4, 9, 20, 23, 29, 33, 37, 42, - 51, 55, 71, 72, 81, 83, 84, 94, 103, 119 and 131 have a level of activity of 100%.

[813]

Example V.

[814]

Test on Oncopeltus

[815]

Introduced into a plastic container larvae bug cotton (Oncopeltus fasciatus sequesters the L-III) with a follower of dentist that has been treated by a composition containing TMs active material to a desired concentration..

[816]

At the end of the desired time (L III to imago) determined the fatality rate of larvae or hatching imagoes, in %. The valeurvl00 % means that all beetle larvae have been killed or that none insect perfect hatched the last larval stage.

[817]

In this test the OH finds that with an active-substance concentration of 0.1% the compounds Nos. 23, 29, 33, 37y and 72 cause lethality of 100%.



[818]

The compounds of the formula I <IMAGE> (I) in which R1 to R5 denote hydrogen; alkyl, alkoxy, alkylmercapto, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy each of which can be halogenated, halogen or nitro, R6 to R10 denote hydrogen; alkyl, alkoxy, alkenyloxy, alkylmercapto, alkenylmercapto, alkylsulfonyl or C3-hydroxyalkyl each of which can be halogenated, (substituted) benzyloxy, alkoxycarbonyl or NRR', and R7 and R8 together can form a (substituted) alkylenedioxy radical, X denotes OR11 in which R11 denotes optionally halogenated alkyl, cycloalkyl, alkenyl or alkynyl or optionally halogenated benzyl, or SR12 in which R12 denotes alkyl or benzyl each of which can be halogenated, and Y denotes oxygen or sulfur, subject to the proviso that, if R1 and R5 both denote fluorine and R2, R3 and R4 denote hydrogen, the radicals R6 to R10 must not each represent halogenated (C1-C6)-alkyl or halogen, possess an intense action against a broad spectrum of harmful insects.



.!. Compounds of formula I

in which

The R ^ RG are each, independently of one another: 1 * hydrogène; C alkyl ^ - GC, alkoxy, c ^ - GC, a aJJcylthiaSL c ^ - GC, alkylsulfinyl C ^ - GC, GC - alkylsulfonyl or alkylsulphonyloxy c ^ - GC, the radicals just mentioned can carry as substituent (e) one or more halogen atoms; halogen or nitro radical, the rg to R ^ Q-|each represent, independently from each jetproof. other :. ; hydrogen; C alkyl - ^ GC, the Cj alkoxy - ^ GC, the Cj GC-alkenyloxy,1111 the c ^ alkylthioien - GC, alkenylthio c ^ GC, alkylsulfonyl C ^ - GC or hydroxyalkyl GC, the radicals just mentioned can carry as substituent (e) one or more halogen; halogen; TOUT residue; benzyloxy optionally porteut of a halogen, a halogen-alkyl C ^ GC, a lower alkoxy C ^ - GC, a cyano or nitro; alkoxycarbonyl having 1 'alkoxy contains 1 to 9 carbon atoms; a radical NRR' wherein R and R 'are each, independently of one another, an alkyl in the Cj - ^ GC, GC GC-alkenyl, alkynyl GC-GC(these substituents can also carry one or more halogen atoms), a halogen, nitro or cyano, or R and R' form together with the nitrogen atom and common a saturated or six-membered ring which may contain, as link of its cycle, atom. oxygen or sulfur or a radical NR in " (the symbol R '1 designating C alkyl - ^ c-a-j) - and which may have an alkyl

5 C. ^ - GC; Of Rj and RG can further form together a radical alkylene-dioxyethylene contènant one or two carbon atoms and optionally bearing a halogen or a radical CFg,

X represents a radical gold ^ ^ lo and wherein R denotes C alkyl optionally halogenated ^ - GC, GC or GC-cycloalkyl, alkenyl C ^ - GC, alkynyl or GC-GC1111 benzyl optionally halogenated, or X represents a radical ^ ^ the SR wherein R denotes C alkyl - or benzyl ^ GC, each denoting a-5 Caux that can carry as substituent (e) one or more halogen, and

Y represents oxygen or sulfur,

with the proviso that, when R2 and RG each represent fluorine and R2 , r.3 and R4 each represent 1 'hydrogène,-to-O or halogen. ' uCN of. rgrams to R.10 or a halogenated alkyl the Cj GC-

2. A process for preparing compounds of formula I according to claim 1, characterized in that method is 5 esters are reacted arêne-to-fchiojcarboximidiqû.es substituted acids of formula II

>

in which

claim ., with compounds of any of formulas III and IV

wherein RG is to R ^ Q and Y have the meanings given in claim 1 and confectioneries represents a halogen other than a basic ëliminable.

3. A process for preparing compounds of formula I according to claim 1, characterized in that method is reacted ester derivatives (alkylthio) - acidesarènecarboximidiquæsubstitués of formula V. S

wherein R ^ ^ to R, X and Y have the meanings given in claim 1 andhas meaning of zi and may further be a halogen, with substituas anilines of formula VI

wherein Rg to R ^ Q have the meanings given in claim 1.

4. A process for preparing compounds of formula I according to claim 1, characterized in that method are reacted anthropodicidal-a 1, 3, 5 substituted according to formula VII:

wherein to and Y have the meanings as defined in claim 1, hydroxylic compounds with substituted or thiolic respectively according to formula VIII or formula IX:

in which and Rl2 have the meanings given in claim 1.

5. Insecticides characterized in that they contain an effective amount of a compound of formula I.

i claim as well as formulation auxiliaries.

6. A method of combating insect pests, characterized in that method is applied to these insects, on their development stages or on plants bearing such organisms an effective amount of a compound of formula I.

7. The application of the compounds of formula I for the prevention of insect pests.

RX1 0:00 R.12 shush

(VIII) (IX.)