DE3418167A1 - Use of amides for improving the crop plant compatibility of herbicidally active heteroaryloxyacetamides - Google Patents

Description

BAYER AKTIENGESELLSCHAFT 5090 Leverkusen, Bayerwerk

Group administration RP
Patent department Bi / AB

(Hb)

J C. ! 4M 1984

Use of amides to improve crop plant compatibility of herbicidally active heteroaryloxyacetami the

The invention relates to the use of known amides as antidotes for improving the tolerance of crop plants of certain herbicidally active heteroaryloxyacetami the.

The invention also relates to new combinations of active ingredients, which consist of known amides and known herbicidally active HeteroaryLoxyacetamiden and particularly good selective herbicides Possess properties.

Under ¹ GegenmitteIn '(' Safener ', 'Antidots') are to be understood in the present context substances which are able to specifically antagonize the harmful effects of herbicides on crops, ie to protect the crops without affecting the herbicide noticeably influencing the weeds to be controlled.

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It is known that numerous herbicidally active heteroaryloxyacetamides more or less severe damage when used for weed control in maize and other crops the cultivated plants.

It is also known that numerous amides are suitable for damaging crop plants caused by herbicidal active ingredients, in particular thiol carbamates and acetanilides can be reduced (see e.g. DE-OS 22 18 097, DE-OS 28 28 265, US-PS 4,021,224, US-PS 4,124,376, U.S. Patent 4,137,070).

The applicability of these substances as an antidote is however to a large extent dependent on the respective herbicidal active ingredient.

It has now been found that the known amides of the formula (i)

0 ι Il / ^R RCN (I)

in which

R stands for hydrogen, halogen or for each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, Cycloalkenyl, Bi eye loa I ky I, Bi eye loaIkenyI, TrieyeLoaIkyI, aryl, heteroaryl, alkoxy, ALkenyloxy, Alkinyloxy, aryloxy, carbamoyl, alkoxycarbonyl or DithioLanyl stands and

R ^{1 and r 2,} independently of one another, each represent hydrogen, formyl, chlorosulfonyL or each optionally substituted alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkylthio, alkylcarbonyL, alkoxycarbonyL, phenyl, phenoxy, phenylsulfonyyl, or heterocyclic , also for amino,

Le A 23 009

for AlkyLidenimino or for optionally substituted Al kylcarbonylamino or Di (a Iky lcarbonyL) -amino stand, or

R ¹ and r2 together with the nitrogen atom to which they are bonded for each optionally substituted alkylidenimino, pyrrolidinyl, piperidinyl, piperidonyl, perhydroazepi ny L, perhydroazo egg I, dihydropyrazoLyI, dihydro- or tetrahydropyridinyL, azabicyclononyL, perhydro-1ynyl, 3-oxazinyL, 1,3-oxazolidinyI, 1,4-piperazinyL, perhydro-1,4-di azepinyl, dihydro-, tetrahydro- or perhydrochino LyL- or -isochinoLyL, IndoLyl, dihydro- or perhydroindolyl,

are outstandingly suitable as antidotes to improve the tolerance of crop plants to herbicidally active substances HeteroaryLoxyacetans of the formula (II),

R ³ Het - 0 - CH ₂ - CO - N (II)

in which

Het for an optionally substituted 5-membered Heterocycle, which can also be benzoannelated can and

R ³ and R ^ independently represent hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkoxyalkoxy, heterocyclyl or optionally substituted aryl or

R ³ and R ^ together with the nitrogen atom to which they are attached represent an optionally substituted, saturated or unsaturated hetero-

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copy Jf

-Jr-

cyclus, which may contain other heteroatoms.

It was also found that the new active ingredient combinations consisting of

5 - an amide of formula (I) and

- At least one herbicidal heteroaryloxyacetamide Form I (II)

are ideal for selective weed control in crops of useful plants.

Surprisingly, the crop plant tolerance is of herbicidal heteroaryloxyacetamides of the formula (II) decisively improved by the use of amides of the formula (I). It is also unexpected that the invention Combinations of active ingredients from an amide of the formula (I) and a herbicidal heteroaryloxyacetamide of the formula (II) have better selective properties than those in question Active ingredients alone.

The inventively usable amides are by Formula (I) generally defined. Amides of the formula (I) are preferred in which

R - represents hydrogen, fluorine, chlorine, bromine; moreover - stands for the radical - CO ~ ^ _R 6, where R ⁵ and R ^{6 are} identical or different and each represent hydrogen and each straight-chain or branched alkyl, alkenyl, alkynyl or cyanoalkyl with

each have up to 8 carbon atoms; furthermore R - for given I Ls single or multiple, equal or differently substituted, straight-chain or branched Is alkyl of 1 to 20 carbon atoms, where as substituents come into question:

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Hydroxy, halogen, especially fluorine, chlorine, bromine, iodine, cyano, cyanato, thiocyanato; each straight chain or branched alkoxy, alkylthio, alkylcarbonyl, A IkyI carbonyloxy, alkoxycarbony I, haloalkoxy, Halohydroxy-a Ikoxy, HaloalkylcarbonyI, HalogenaIkoxycarbonyI, HalogenaLkyIcarbonyI oxy and Haloalkenylcarbonyloxy with up to 6 each Carbon atoms and optionally up to 9 identical or different halogen atoms, especially fluorine, Chlorine, bromine; also, if necessary, simply or multiply, identically or differently substituted by halogen, lower alkyl and / or lower alkoxy Phenyl, phenoxy, phenylthio or thienyl; also cycloalkyl, atoms with 3 to 7 carbon atoms as well

ic ^ - R ^D - "R ³ ^ R-"

'3 the radicals -N ^ " _Λ , -QN ^" _Λ , -0-CH ₂ -CN ^. _r6 and

- " ^R κ" a Q

-S02 ~ N ^ _R 6 where R ⁵ and R ^ö each have the meanings given above; also R

- for optionally single or multiple, identical or different substituted, straight-chain or branched Alkenyl having 2 to 8 carbon atoms, where as substituents come into question:

Hydroxy, halogen, especially fluorine, chlorine, bromine, straight-chain or branched alkoxycarbonyl with up to to 6 carbon atoms, as well as each optionally single or multiple, the same or different Halogen, especially fluorine, chlorine, bromine, lower alkyl or lower alkoxy substituted phenyl or phenoxy; furthermore R

- for straight-chain or branched alkynyl with 2 to 8 Carbon atoms; also 'R

- for each, possibly single or multiple, the same

or differently substituted cycloalkyl, cyclo-

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EPO COPY

alkenyl, Bi eyeLoaLkyL, Bi eyeLoaLkenyL or tricycloalkyL with up to 12 carbon atoms each, where possible substituents are:

straight-chain or branched alkyl with 1 to

'R carbon atoms, phenyl and the radical -C-N

0 R ⁶

where R ⁵ and r6 dj _e have the meaning given above; furthermore R

for possibly single or multiple equal or variously substituted aryl with 6 to 10 carbon atoms stands, with possible substituents:

Halogen, in particular fluorine, chlorine, bromine, iodine, nitro, carboxy - also in the form of the carboxylate anion -, in each case straight-chain or branched alkyl, alkoxy, HalogenaIky I, A IkyL carbony I, HaLogenaLkyL carbonyl and HaLogena Iky LcarbonyLamino each with up to 4 carbon atoms and optionally up to 5 identical or different halogen atoms! In particular fluorine, chlorine, bromine, and the radical -CO-N ^ J ^, where R ⁵ and R ^{6 are} the above

have given meaning, also R for each optionally single or multiple, identically or differently substituted furyl, thienyl, Pyridyl or dithiolanyl, where as substituents come into question:

Halogen, in particular fluorine, chlorine, bromine, straight-chain or branched alkyl with up to 4

- ■ "R ^ carbon atoms, as well as the remainder -CO-N. *,

where R ⁵ and R ^ have the meaning given above, and finally R

for each possibly single or multiple, each substituted identically or differently by phenyl or halogen, in particular fluorine, chlorine, bromine straight-chain or branched alkoxy, alkenyloxy,

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EPOCOPV

Alkinyloxy, alkoxycarbonyL or phenoxy, and

R ¹ and R ^, which are the same or different, are independent of one another

- for hydrogen, formyl, chlorosulfony I or for each optionally single or multiple, identical or different by halogen, especially fluorine, chlorine, bromine or lower alkyl substituted phenyl, phenoxy or Pheny IsuIfonyI are available, furthermore

- for possibly single or multiple, the same or

differently substituted, straight-chain or branched Are alkyl having 1 to 12 carbon atoms, where as substituents come into question:

Hydroxy, mercapto, cyano, halogen, especially fluorine, chlorine, bromine, iodine; each straight-chain or branched alkoxy, alkoximino, alkylcarbonyl, alkylcarbonyloxy, Alkoxycarbonyl, alkoxycarbonyloxy, A Lky11hiocarbonyloxy, HalogenaIkyIcarbonyloxy and Alkylsulfonyloxy each with up to 6 carbon atoms and optionally up to 5 equal or different halogen atoms, especially fluorine, Chlorine, bromine; also alkylaminocarbonyloxy, dialkylaminocarbonyloxy, Alkenylaminocarbonyloxy and dialkenylaminocarbonyloxy each with up to 6 Carbon atoms in each straight chain or branched alkyl or alkenyl parts; further Cyc loaIkyL aminocarbonyloxy with 3 to 7 carbon atoms in the cycloalkyl part, optionally simple or several times, identically or differently through halogen, in particular fluorine, chlorine, bromine, or lower Alkyl substituted pheny I aminocarbonyloxy, as well possibly one or more times the same or differently substituted by halogen, in particular fluorine, chlorine, bromine, or lower alkyl

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Cycloalkyl, having 3 to 7 carbon atoms, optionally single or multiple, identical or different, by nitro, halogen, in particular fluorine, chlorine, bromine, lower alkyl or dioxyalkylene substituted phenyl, in each case one or more times, the same or furyl which is differently substituted by halogen, in particular fluorine, chlorine, bromine or lower alkyl, TetrahydrofuryL, Pyrazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazo Iy I, Oxadiazo Iy I, pyridyl or Pyrimidinyl as well as, if necessary, one or more times, identically or differently through each lower A I ky I, Haloalkylcarbonyl, halophenoxyalkylcarbonyl and HalogenaIky lcarbonylaminoa Iky L substituted

1 2 amino; also R and R

15 ~ for any given Lts single or multiple, the same or variously substituted, straight-chain or branched alkenyl, A L ka d "i eny I, or alkynyl with each to 8 carbon atoms, where as substituents come into question:

Halogen, especially fluorine, chlorine, bromine, cyano as well straight-chain or branched alkoxy, alkylcarbonyL or alkoxycarbonyL each with up to

1 2 6 carbon atoms; furthermore R and R

- for each, possibly e-single or multiple, the same or cycloalkyl or cycloalkyl differently substituted by halogen, in particular fluorine, chlorine, bromine, or lower alkyl Are cycloalkenyl with 3 to 8 carbon atoms each; aside from that

- for each, possibly single or multiple, the same or differently substituted and / or benzanne-11osed Piperidyl, pyridyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, fluorenyl, phthalimidoyl or dioxanyl, with possible substituents:

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Halogen, especially fluorine, chlorine, bromine, cyano as well in each case straight-chain or branched alkyl or Alkanediyl each having 1 to 4 carbon atoms ^

1 2 also R and R

- for straight-chain or branched alkoxy, alky I-thio, A I kyI carbonyI, alkoxycarbonyI, halogenaIkyIcarbonyL or HalogenaIkoxycarbonyI are each with up to 6 Carbon atoms and optionally up to 5 of the same or different halogen atoms, especially fluorine,

- 12

10 chlorine, bromine; and also R and R

- for possibly single or multiple, the same or differently substituted amino or A IkyLidenimi no stand, with possible substituents:

in each case straight-chain or branched alkyl, alkenyl, Alkynyl, A IkyIcarbonyl or Halogena I kyI carbony I with each up to 8 carbon atoms and optionally up to 5 identical or different halogen atoms, in particular fluorine, chlorine, bromine; or but

R ¹ and R ² together with the nitrogen atom to which they are attached,

for each possibly single or multiple, the same or variously substituted alkylideneamino, pyrrolidinyl, Piper idinyl, piperidonyl, perhydroazepinyl, P e r hydroazocinyl, DihydropyrazoIyI, dihydro- or tetrahydropyridyl, Azabieyelonony I, morpholinyl, perhydro-1,3-oxazinyl, 1,3-OxazoIidinyI, 1,4-Piperaziny I, Perhydro-1,4-diazepinyl, Dihydro-, tetrahydro- or perhydrochino Iy I or - isoquinolyl, indolyl, dihydro- or perhydroindolyl

30, with possible substituents:

Hydroxy, halogen (especially fluorine, chlorine, bromine), cyano, Formyl; each straight or branched chain.

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COPY

optionally doubly linked alkyl, alkanediyl, Alkoxy, dioxyalkylene, alkylcarbony I, ALkoxycarbony I and HalogenaIky I carbonyl each having up to 8 carbon atoms, each straight-chain or branched ■ Alkylamino or dialkylamino with up to 4 each Carbon atoms in the individual alkyl parts, each optionally single or multiple, the same or different from halogen, in particular fluorine, chlorine, bromine, nitro or lower alkyl, haloalkyl,

• JO alkoxy, alky L carbonyl or alkoxycarbony I substituted phenyl, naphthyl, pyridyl or piperidinyl or in each case one or more times, the same or different from halogen, in particular fluorine, chlorine, bromine, lower alkyl or halogeno-alkylcarbonyI substituted straight or branched cyclo propylalkyl, Cyclohexyla Iky I, Pi peridinyla Iky I, phenylalkyl or Phenyla IkenyI with up to 4 carbon atoms in the respective alkyl or alkenyl parts.

Particularly preferred are amides of the formula (I) in which

2Q R - represents hydrogen or chlorine; furthermore R

^ R ^{5 stands} for the radical -CO-N ^ _ ₆ , where R ⁵ and R ⁶ ,

are identical or different and each independently represent hydrogen, methyl, ethyl, allyl, propargyl, but-1-yn-3-yl, 3-ethylbut-1-yn-3-yI or 2-cyanoprop-2-yl ; furthermore R represents straight-chain or branched alkyl of up to 15 carbon atoms; aside from that

for straight-chain or branched haloalkyl with 1 to 6 carbon atoms and 1 to 9 the same or 3Q different halogen atoms, especially fluorine, Chlorine, bromine and iodine; aside from that

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"" ___. - For single to triple, identically or differently substituted, straight-chain or branched alkyl with 1 to Carbon atoms, with possible substituents:

Hydroxy, fluorine, chlorine, bromine, cyano, cyanato,

Thiocyanato, methoxy, ethoxy, methylthio, ethylthio, acetyl, propionyl, acetoxy, propionyloxy, - MethoxycarbonyI, ethoxycarbony I, 1,1,3,3-tetrachloro 2-hydroxyprop-2-yloxy, 1,1,1,3,3-pentachloro-2-hydroxyprop-2-yloxy, chloroacetyl, dichloroacety I,

Chloracetoxy, dichloroacetoxy, pentachlorobutadien-1-yLcarbonyloxy, in each case optionally one to phenyl substituted three times, identically or differently by chlorine, methyl or methoxy, phen oxy, phenylthio or thienyl; also cyclopropyl,

■ *** " R ^ cyclopentyl, cyclohexyl; and the radicals -N,

⁵ S ^x 6

"C0-N ^ _{r6 r} -0-CH ₂ -CO-N ^ _r6 and -

where R- * and, R ^{0 are} identical or different and each independently represents hydrogen, methyl, ethyl, allyl, propargyl, but-1-yn-3-y I,

3-methyl-but-1-yn-3-yI or 2-cyanoprop-2-yI; also R

- For single to triple, identically or differently substituted, straight-chain or branched alkenyl with 2 to 5 carbon atoms, with as substituents come into question:

Hydroxy, fluorine, chlorine, bromine, methoxycarbony I, Ethoxycarbonyl and in each case optionally one to three times, identical or different, by fluorine, Phenyl substituted with chlorine, methyl or methoxy

or phenoxy; furthermore R

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- for straight-chain or branched alkynyl with 2 to Carbon atoms; aside from that

for each possibly one to five times, the same or variously substituted cyclopropyl, cyclopentyl. Cyclohexyl, Cycloheptyl, CyclohexenyI, Bicyclohep- tenyl, bicyclooctyI, bicyclononyl and tricyclodecyI stands, with possible substituents:

Methyl, ethyl, phenyl and the radical -C0-N ^ _r6 , where R ⁵ and R ^{6 are} identical or different, and each independently represents hydrogen, methyl, ethyl, allyl, propargyl, but-1-yn-3-yL , 3-methylbut-1-yn-3-yI or 2-cyanoprop-2-yI, also R

- is optionally mono- to triple, identically or differently substituted phenyl, where the sub-

Stituents come into question:

Fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, methoxy, ethoxy, carboxy - also in the form of CarboxyLatanions -, TrifluormethyI, Chloracet amido, dichloroacetamido and the radical -CO-N ^ _R g, where R ^ and R ^ are the same or different, and each independently represents hydrogen, methyl, ethyl, allyl, propargyl, but-1-yn-3-yI, 3-methylbut-1-yn-3-yI or 2-cyanoprop-2-yI

25 stand; furthermore R

- for in each case one to three times, the same or differently substituted Fury I, thienyl, pyridyl or Dithiolanyl, with possible substituents:

Chlorine, methyl, ethyl and the remainder -CO-N ^,

30 where R ⁵ and R ^ are identical or different, Le A 23 009

copy m

and each independently represent hydrogen _/ methyl, ethyl, allyl, propargyl, but-1-yn-3-yl, 3-methylbut-1-yn-3-yl or 2-cyanoprop-2-yl; and finally R

- for each, possibly one to three times, the same or methoxy, ethoxy, allyloxy, propargyloxy differently substituted by fluorine, chlorine, bromine or phenyl, Butinyloxy, methoxycarbonyI, ethoxycarbony I or phenyl stands, and

r1 and R ^, which are the same or different, are independent from one another

- for hydrogen, formyl, chlorosulfonyL or for each optionally one to three times, the same or different from fluorine, chlorine, bromine or methyl sub substituted phenyl, phenoxy or PhenyIsulfonyL; further

- for straight-chain or branched, optionally mono- to triple, identically or differently substituted Alkyl having 1 to 8 carbon atoms, where as

20 substituents are possible:

Hydroxy, mercapto, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, butoxy, methoximino, Ethoximino, acetyl, propionyl, acetoxy, propionyloxy, methoxy.carbonyI, ethoxycarbonyI, methoxycar- bonyloxy, ethoxycarbonyloxy, Met hy Ithiocarbonyloxy, EthyIthiocarbonyloxy, chloroacetoxy, dichloroacetoxy, Met hy LsuIfonyloxy, EthyLsuIfonyloxy, methylaminocarbonyloxy, dimethylaminocarbonyloxy, Ethylaminocarbonyloxy, diethylaminocarbonyloxy,

PropyI aminocarbonyloxy, butylaminocarbonyloxy,

ALlylaminocarbonyloxy, DialLylaminocarbonyloxy, Cyclohexylaminocarbonyloxy and optionally one to three times, the same or different

. Le A 23 009

EPO COPY

Chlorine or methyl substituted phenylaminocarbonyloxy; furthermore in each case optionally one to five times, identically or differently substituted by chlorine or methyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl; phenyl optionally substituted once to three times, identically or differently by nitro, fluorine, chlorine, bromine, methyl or dioxymethylene, in each case optionally mono- or disubstituted, identically or differently by methyl, ethyl, propyl or chlorine substituted furyl, tetrahydrofury I, pyrazolyl, oxazolyl, Isoxazolyl, thiazolyl, thiadiazo IyI, oxadiazolyl, pyridyl or pyrimidinyl; and optionally once or twice, identically or differently by methyl, ethyl, chloroacetyl, dichloracety I, chlorophenoxyacetyl, dichloroacetamidomethyl or dichloroacetyl

1 amidoethyl substituted amino; also R and R

- for each possibly single or double, the same or different from chlorine, methoxy, ethoxy, acetyl, methoxycarbonyl, ethoxycarbonyl or cyano substituted straight-chain or branched alkenyl, alkaodienyl or alkynyl with each have 3 to 5 carbon atoms; further

- for each one to five times, if applicable, the same or differently substituted by chlorine or methyl CycLopropyl, cyclopentyl, cyclohexyl, cyclohexenyl or cyclooctyl; aside from that

- for each, if necessary, one to three times, the same or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, propanediyl or butanediyl and / or benzannelated piperidyl, pyridyl, thienyl, oxazolyl, isoxazolyl, thiadiazoly I, fluorenyl, phthalimidoyl or dioxanyl; aside from that

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- for methoxy, ethoxy, propoxy, butoxy, methylthio, ethylthio, propylthio, butylthio, acetyl, chloroacetyl, You loracetyI, MethoxycarbonyL / EthoxycarbonyL, ChlorethyLoxycarbonyL or BromethyLoxycarbonyL stand and

5 as well

- for possibly single or double, equal or amino or amino substituted differently by methyl, ethyl, allyl, propargyl, acetyl, chloroacetyl or dichloroacetyl Propylidenimino stand, or else

and R ^ together with the nitrogen atom to which they are bound,

- for each one to five times, if applicable, the same

or differently substituted Met hy I i dem "mi no, ethylidenimino, propylidenimino, pyrrolidinyl, piperidinyl, piperi- donyl, Perhydroazepiny I, Perhydroazociny I, Dihydropyrazo Iy I, Dihydro- or tetrahydropyridyl, azabicyclononyl, morpholinyl, Per hydro-1, 3-oxaziny I, "1, 3-Oxazo L i di ny I, 1,4-piperazinyl, Perhydro-1,4-diazepiny I, dihydro- , Tetrahydro or Perhydrochino Iy I or - isoquinolyl, indolyl, Di hydro- or perhydroindolyl, where the substituent ducks are eligible:

Hydroxy, fluorine, chlorine, bromine, cyano, formyl, methyl, Ethyl, propyl, butyl, ethanediyl, propanediyl, methoxy, ethoxy, propoxy, butoxy, dioxyethylene, dioxypropylene,

Dioxybutylene, acetyl, propionyl, chloroacetyl,

Di ch Io racety I, ot-Ch Io rpropi ony I, Met hoxy carbony I, Ethoxycarbonyl, methylamino, ethylamino, dimethylamino, diethylamino, in each case optionally one to three times, identically or differently due to fluorine,

Chlorine, bromine, nitro, methyl, ethyl, methoxy, eth-

oxy, trifluoromethy I, acetyl, propionyl, methoxycar-

phenyl substituted with bonyl or ethoxycarbonyl, Le A 23 Q09

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-Wr-

Naphthyl or piperidinyl or each optionally substituted one to three times identically or differently by chlorine, methyl, chloroacetyl or dichloroacetyl CyclopropyImethy I, Cyclohexylmethy I, Piperidinylethyl. PiperidinyIpropyI, benzyl, phenylethyl or Pheny Ipropeny I.

In the context of this invention, the terms "lower alkyl", "lower alkoxy" etc. denote corresponding radicals having 1-4 carbon atoms. In particular, the following compounds are the general ones Formula (I) named:

Table 1

R-CO-N

(I)

Example No.

C ₂ HC ₂ H ₅

1-2 Cl -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ 1-3 CH ₃ H -CC = CH
¹ CH ₃ 1-4 CH ₃ H ^CF 3
-C-OH 1-5 CH ₃ -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

-SO ₂ -

nC ₃ H ₇ H CH ₃
-9-C = CH
CH ₃ CH ₃ nC ₃ H ₇ CH ₃ -CH-C = CH nC ₃ H ₇ -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ Le A 23 009

EPO COPY Sk

Table 1 (continued) Example No. RR ¹

34lolo /

1-10 TC ₃ H ₇ CH ₃

1-11 nC _A H ₉ H

1-12 (CH ₃ ) ₃ C-CH ₂ -H

1-13 (CH ₃ ) ₃ C-CH ₂ -CH ₃

1-14

1-15 1-16

CH ₃ CH ₃ - (CH ₂ ) ₂ -CH- H

CH ₃ CH ₃ - (CH ₂ ) 2 ~ CH- CH ₃

CH ₃ CH ₃ - (CH ₂ ) 2-CH- -

CH ₂ -CH = CH ₂

1-17 nC ₆ H ₁₃

1-18 nC ₆ H ₁₃ 1-19 nC ₆ H ₁₃

CH ₃

-CH ₂ -CH = CH ₂

₃ 1-20 CH ₃ - (CH ₂ ) ₂ -C- -CH ₂ -CH = CH ₂

CH ₃ -H ₃

1-21 (CH ₃ ) ₃ C-CH ₂ -CH-CH 2 -H

CH ₃ -CH-

1-22 nC ₉ H ₁₉

1-23 n-CoH-, 9

1-24 In-C ₁₁ H ₂₃

1-25 HC ₁₁ H ₂₃

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-CH ₂ -CH = CH ₂ H

-CH ₂ -CH = CH _{2 3} CH-C = CH CH ₃ CH- CSCH ςπ ₃ (J-CN CH ₃

CH ₃ C-C = CH CH ₃

CH ₃ C-C = CH CH ₃

H ₃ HC = CH

-CH ₂ -CH = CH ₂

CH ₃

-CC = CH CH ₃

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂

CH ₃ -CC = CH Ch ₃

CH ₃

-CC = CH CH ₃

-CH ₂ -CH = CH ₂

ςπ ₃

-CC = CH CH ₃

-CH ₂ -CH = CH ₂

EPO COPY

Room :.

Table 1 (continued) Example No. R.

1-26 nC ₁₃ H ₂ 7

1-27 CL-CH ₂ -

1-28 Cl-CH ₂ -

1-29 CL-CH ₂ -

1-30 CL-CH ₂ -

1-31 Cl-CH ₂ -

1-32 CL-CH ₂ -

1-33 CL-CH ₂ -

1-34 CL-CH ₂ -

1-35 CL-CH ₂ -

1-36 Cl-CH ₂ -

1-37 CL-CH ₂ -

1-38 Cl-CH ₂ -

1-39 CL-CH ₂ -

1-40 CL-CH ₂ -

1-41 CL-CH ₂ -

1-42 CL-CH ₂ -

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-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ H -CH ₂ -CH (CH ₃ ) ₂ H -C (CH ₃ > 3 H CH ₃
-CC ₂ H ₅
CH ₃ H CH ₃
-CH-CH ₂ -CH (CH ₃ ) ₂ H -CH ₂ -C = CH ₂
I. CH ₃ H CH ₃
-C-C = CH
CH ₃

CN

C2H5 ■ fC ₂ H ₅

CN

-CH ₂ CH ₂ -Br

-CH ₂ CH ₂ -OCH ₃

■ CH ₂ -CH (OCH ₃ ) ₂

-CH

CL "

-CH ₂ -NH-CO-CH

-CH-NH-CO-CH ₂ Cl

^ _ ^ - CH ₃

CH ₃

C ₂ H ₅

EPO COPY P

Table 1 (continued) Example No. R.

1-43 Cl-CH ₂ -

1-44 Cl-CH ₂ -

1-45 Cl-CH ₂ -

1-46 Cl-CH ₂ -

1-47 Cl-CH ₂ -

1-48 Cl-CH ₂ -

1-49 Cl-CH ₂ -

1-50 Cl-CH ₂ -

1-51 Cl-CH ₂ -

1-52 Cl-CH ₂ -

1-53 Cl-CH ₂

1-54 Cl-CH ₂ -

1-55 Cl-CH ₂ -

1-56 Cl-CH ₂ -

1-57 Cl-CH ₂ -

1-58 Cl-CH ₂ -

1-59 Cl-CH ₂ -

CH ₃ CH ₃ CH ₃

CH ₃

CH ₃

CH ₃ CH ₃

CH ₃

CH ₃ CH ₃

C ₂ H ₅

C ₂ H ₅ C ₂ H ₅

C ₂ H ₅ C ₂ H ₅

C ₂ H ₅ C ₂ H ₅

CH (CH ₃ ) ₂ (CH ₂ ) ₃ -CH ₃ HC ₂ H ₅

H-CH (CH ₃ ) ₂ H ₃

-CH ₂ -C = CH

CH ₃
CH- C = I. CH ₂ CH Cl CH ₂ i CH ₂ < CH ₂ 4th = CH ₂ -CN C. > 1>

-CH-C ₂ H ₅

-CH ₂ -CH ₂

-CH ₂

CH ₃

rl

CH ₃

CH ₃ CH ₃

CH ₃

Le A 23 009 EPO COPY

Table 1 (continued) Example No. R.

1-60 Cl-CH ₂ -

1-61 CL-CH ₂ -

1-62 CL-CH ₂ -

1-63 Cl-CH ₂ -

1-64 -Cl-CH ₂ -

1-65 Cl-CH ₂ -

1-66 CL-CH ₂ -

1-67 CL-CH ₂ -

1-68 CL-CH ₂ -

1-69 Cl-CH ₂ -

1-70 Cl-CH ₂ -

1-71 Cl-CH ₂ -

1-72 CL-CH ₂ -

1-73 Cl-CH ₂ -

1-74 Cl-CH ₂ -

1-75 Cl-CH ₂ -

1-76 CL-CH ₂ -

1-77 Cl-CH ₂ -

1-78 Cl-CH ₂ -

1-79 CL-CH ₂ -

1-80 CL-CH ₂ -

Le A 23 009

-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃

-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃

-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃

-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₃ -CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂ -CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂

-CH ₂ CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₂ CH ₃ -CH-C ₂ H ₅

CH ₃

- (CH ₂ ) ₅ -CH ₃ -CH ₂ -CH = CH ₂

CH ₂ -CH (CH ₃ ) ₂ C (CH ₃ ) ₃

CH- (CH ₂ ) ₂ -CH ₃ CH ₃

-CH:

CH ₃

CL CL

-Cl

I I

-CH;

-CH ₂ -Cl

-CH ₂

-CH ₂ CH ₂ CH ₂ CH ₃

CH ₃ -CH-C ₂ H ₅

-CH ₂ -CH (CH ₃ ) ₂ -CCH ₂ ) ₄ -CH ₃

-CH ₂ -

-CH ₂ CH ₂ CH ₂ CH ₃ -CH ₂ -CH (CH ₃ ) ₂ -CH = CH ₂ -CH ₂ -CH (CH ₃ ) ₂

-CCH ₂ ) ₅ -CH ₃ -CH ₂ -CH = CH ₂

EPO COPY M

&
Table 1 (continued) -. R. Ri - -CH ₂ CH ₂ -OH
-CH ₂ CH ₂ OCH _{3 R1} 3A18167 E.g. Ni CL-CH ₂ -
Cl-CH ₂ - -CH ₂ CH ₂ -OH
-CH ₂ CH ₂ OCH ₃ " ^N Cr2 1-81
1-82

1-83 CL-CH ₂ - -CH ₂ CH ₂ OC ₂ H ₅ -CH ₂ CH ₂ OC ₂ H ₅

1-84 Cl-CH ₂ - -CH ₂ CH ₂ O-CO-NH-CH ₃ -CH ₂ CH ₂ O-CO-NH-CH ₃ 1-85 CL-CH ₂ -CH ₂ CH ₂ O-CO-NH-CH ₂ -CH ₂ CH ₂ O-CO-NH-CH ₂

OH = CH ₂ CH = CH ₂

1-86 Cl-CH ₂ - -CH ₂ CH ₂ 0-C0-NhV ~ N -CH ₂ CH ₂ 0-C0-NHY ~~ y

1-87 CL-CH ₂ - -CH ₂ CH ₂ O-CO-NH -CH ₂ CH ₂ O-CO-NH
^α ή 1-88 CL-CH ₂ - 1-89 CL-CH ₂ - H 1-90 CL-CH ₂ H ₅ C ₂

Le A 23 009

ti

CH ₃

C ₂ H ₅

"Λ 1-91 CL-CH ₂ - -N

.N (CH ₃ ) ₂ 1-92 CL-CH ₂ - -N = C

N (CH ₃ ) ₂ CH ₃

1-93 1-CH ₂ - H - ^ - C = CH

CH ₃

1-94 1-CH _{2 -CH 3} -CH-C = CH

1-95 1-CH ₂ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

EPO COFr

Example No. - _____
R. - ■ _
Rl r2 1-96 Cl ₂ CH- ^ —___ ■■ __
H -CH ₂ -CHCCH ₃ ) 1-97 CL ₂ CH- H -CCCH ₃ ) ₃ 1-98 CL ₂ CH- H CH ₃
-CC ₂ H ₅
CH ₃ 1-99 Cl ₂ CH- H -CH ₂ -CH = CH ₂ 1-100 CL ₂ CH- H 9H ₃
-CH ₂ -C = CH ₂

1-101 CL ₂ CH- H - _c

CH ₃

1-102 Cl ₂ CH- H -CH ₂ CH ₂ Br 1-103 CL ₂ CH- H -CH ₂ CH ₂ OH 1-104 Cl ₂ CH- H 9 ^H 3
-CH ₂ -CH-OH 1-105 CL ₂ CH- H -CH ₂ CH ₂ CH ₂ -OH 1-106 CL ₂ CH- H -CH ₂ CH ₂ -OC ₂ H ₅ 1-107 Cl ₂ CH- H -CH ₂ CH ₂ CH2-0CHCCH ₃ ) ₂ 1-108 Cl ₂ CH- H ^ 0C ₂ H ₅
-CH ₂ -CH 1-109 CL ₂ CH- H -C-CN
\ C ₂ H ₅
C2H5

^{> 11} ° ^Cl 2 ^CH - H - _t . _CN

C ₂ H ₅

^{M11 CL2CH} " ^H -CH ₂ CH ₂ -W CH ₃ )

^{1-112 CL} = ^CH - ^H -CH ₂ CH ₂ -N <C ₂ H ₅ , ₂

^{2 H} -CH ₂ CH ₂ CH ₂ -Nh-CO-CHCl ₂

-CH ₂ CH ₂ 4- ² C0 ⁵ -CHCL ₂

Le A 23 009

EPO COPY J!

Table 1 (continued)

Example No. R. Rl - H 1-116 Cl ₂ CH- H 1-117 CL ₂ CH- H 1-118 CL ₂ CH- H 1-119 Cl ₂ CH- H 1-120 CL ₂ CH- H 1-121 Cl ₂ CH- H 1-122 Cl ₂ CH- H 1-123 Cl ₂ CH- H 1-124 Cl ₂ CH- H 1-125 Cl ₂ CH- H 1-126 Cl ₂ CH- H 1-127 Cl ₂ CH- H 1-128 CL ₂ CH- H 1-129 Cl ₂ CH- H 1-130 Cl ₂ CH- H 1-131 Cl ₂ CH- Le A 23 009

- (CH ₂ ) ₃ -N-CO-CHCl ₂ (CH ₂ ) ₃ -NH-CO-CHCl ₂

• CH ₂ - <H
-CH ₂ ^ O ^

-CH ₂ -
-CH ₂ -

• Cl

-CL -Cl

-CH ₂ CH ₂ -NH-CO-CH ₂ Cl

NH-CO-CH ₂ Cl

NO ₂ NH-CO-CHCl ₂

NH-CO-CHCl ₂ NO ₂

NH-CO-CHCL ₂

CH ₃
-C = CH-CN

CH ₃
-C = CH-COOC ₂ H ₅

EPO COPY

Vf

Table 1 (continued) Example No. RR ¹

r2

1-132 Cl ₂ CH-

1-133 Cl ₂ CH-

1-134 Cl ₂ CH-

1-135 CL ₂ CH-

1-136 CL ₂ CH 1-137 Cl ₂ CH- 1-138 CL ₂ CH ' 1-139 Cl ₂ CH ' 1-140 Cl ₂ CH ' 1-141 CL ₂ GH 1-142 CL ₂ CH 1-143 CL ₂ CH

1-144 CL ₂ CH-

1-145 1-146

1-147

CL ₂ CH-Cl ₂ CH-CL ₂ CH-

H H H

H H

^H > O

C ₂ Hf

H r — N '

C ₂ H ₅

-CO-OC ₂ H ₅

-CO-O-CH ₂ CH ₂ CL

-NH-CO-CHCL ₂

9 -N-CO-CHCL ₂

CH ₂ -CH = CH ₂ -N-CO-CHCL ₂

CCH ₃ ) ₃ ί

CH-

CH ₃ ,

C ₂ Hf

CH ₃ CH ₃

Le A 23

EPOCOPY §

Table 1 (continued ^ Example No. RR ¹

I-U8 CL ₂ CH-

1-149 Cl ₂ CH-

1-150 Cl ₂ CH-

1-151 CL ₂ CH-

1-152 Cl ₂ CH-

1-153 CL ₂ CH-

1-154 Cl ₂ CH-

1-155 CL ₂ CH-

1-156 Cl ₂ CH-

1-157 CL ₂ CH-

1-158 CL ₂ CH-

1-159 CL ₂ CH-

1-160 CL ₂ CH-

1-161 CL ₂ CH-

1-162 CL ₂ CH-

Le A 23 009

C ₂ H <

TO

C ₂ H ₅ (CH ₃ ) ₂ CH

(CH ₃ ) ₂ CH

C ₂ H ₅

CL

CL 'CF ₃

, O-CO-NH-C ₂ H ₅ P-CO-NH-CH ₂ -CH = CH ₂ , NH-CO-C ₂ H ₅

NH-CO-CHCL:

H-CO-CHCL ₂

CH ₃

EPO copy f.

ZS-

Table 1 (continued)

Example No. RR ¹ R ²

1-163 CL ₂ CH-

1-164 CL ₂ CH-

1-165 CL ₂ CH-

1-166 CL ₂ CH-

1-167 CL ₂ CH-

1-168 CL ₂ CH-

1-169 CL ₂ CH-

1-170 CL ₂ CH-

1-171 CL ₂ CH-

1-172 CL ₂ CH-

1-173 CL ₂ CH-

1-174 CL ₂ CH-

1-175 CL ₂ CH-

1-176 CL ₂ CH-

1-177 CL ₂ CH-

CH ₃ CH ₃ CH ₃ CH ₃ CH ₃

N-TT-C

-Cf

N N

CH ₃

Br

-CH ₃

-CH ₂ CH ₂ CH ₃ -CH (CH ₃ ) ₂ -CH ₂ CH ₂ CH ₂ CH ₃

-CH-CH ₂ CH ₃ CH ₃

Le A 23 009

EPO COPY A

Table 1 (continued) Example No. RR ¹

1-178 Cl ₂ CH-

1-179 Cl ₂ CH-

1-180 Cl ₂ CH-

1-181 Ct ₂ CH-

1-182 Cl ₂ CH-

1-183 Cl ₂ CH-

1-184 Cl ₂ CH-

1-185 Cl ₂ CH-

1-186 Cl ₂ CH-

1-187 Cl ₂ CH-

1-188 Cl ₂ CH-

1-189 Cl ₂ CH-

1-190 Cl ₂ CH-

1-191 Cl ₂ CH-

1-192 Cl ₂ CH-

1-193 Cl ₂ CH-

Le A 23 009

CH ₃ CH ₃

CH ₃ CH ₃

CH ₃

CH ₃ CH ₃ CH ₃

CH ₃ CH ₃

CH ₃

CH ₃

CH ₃

CH ₃ CH ₃ CH ₃ -CH- (CH ₂ ) ₂ -CH ₃ CH ₃

-CH - CH-CH ₃ CH ₃ CH ₃

-CH = C = CH ₂ -CH ₂ -C = CH

-CH-CS CH I

-CH ₂ CH ₂ -OH -CH ₂ CH ₂ -CN - (CH ₂ ) 2 "N- (CH ₂ ) 2 -N-CO-CHCl ₂

CH ₃

CH ₃

-CH ₂ -O

CH ₃

Cl

Cl

-N = C (CH ₃ ) ₂

^ CO-CHCl ₂ -N ^

CO-CHCl ₂

EPO COPY

Table 1 (continued) Example No. RR ¹

1-194 CL ₂ CH-CH ₃

1-195 CL ₂ CH-CH ₃

1-196 CL ₂ CH-CH ₃

1-197 CL ₂ CH-CH ₃

1-198 CL ₂ CH-CH ₃

1-199 CL ₂ CH-CH ₃

1-200 CL ₂ CH- C ₂ H ₅

1-201 CL ₂ CH- C ₂ H ₅

1-202 CL ₂ CH- C ₂ H ₅

1-203 CL ₂ CH- C ₂ H ₅

1-204 CL ₂ CH- C ₂ H ₅

1-205 CL ₂ CH- C ₂ H ₅

1-206 CL ₂ CH- C ₂ H ₅

1-207 CL ₂ CH- C ₂ H ₅

1-208 CL ₂ CH- C ₂ H ₅

1-209 CL ₂ CH- C ₂ H ₅

1-210 CL ₂ CH- C ₂ H ₅ .

1-211 CL ₂ CH- C ₂ H ₅

1-212 CL ₂ CH- C ₂ H ₅

1-213 CL ₂ CH- C ₂ H ₅

1-214 CL ₂ CH- C ₂ H ₅

Le A 23 009

C ₂ H ₅ '

(CH ₃ ) ₂ CH

CH CH ₃ C ₂ H

C ₂ H ₅ '

C ₂ H ₅

-CH (CH ₃ ) ₂

-CH ₂ CH ₂ CH ₂ CH ₃

-CH-C ₂ H ₅

CH ₃

-CH ₂ -CH (CH ₃ ) ₂ -C (CH ₃ ) ₃ -CH-CH ₂ CH ₂ CH ₃

CH ₃

- (CH ₂ ) ₅ -CH ₃

-C = CH-CH ₃ -CH ₂ CH ₂ -O-CO-CHCL ₂

-CH ₂ CH ₂ -N-CO-CHCL ₂

-CH ₂ -

-CH ₂ -

-CH ₃

CH ₃ .

EPO COPY

Table 1 (continued) Example No. RR ¹ R ²

Ji '

1-215 Cl ₂ CH-C ₂ H ₅

1-216 Cl ₂ CH-C ₂ H ₅

1-217 Cl ₂ CH-C ₂ H ₅

1-218 CJ ₂ CH-C ₂ H ₅

1-219 Cl ₂ CH-C ₂ H ₅

1-220 Cl ₂ CH-C ₂ H ₅

1-221 Cl ₂ CH-C ₂ H ₅

1-222 Cl ₂ CH-C ₂ H ₅

1-223 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-224 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-225 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-226 Cl ₂ CH-

1-227 Cl ₂ CH-

1-228 Cl ₂ CH-

1-229 Cl ₂ CH-

CH ₃ CH ₂ CH ₂ -CH ₃ CH ₂ CH ₂ -CH ₃ CH ₂ CH ₂ "CH ₃ CH ₂ CH ₂ -

1-230 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-231 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-232 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

1-233 Cl ₂ CH- CH ₃ CH ₂ CH ₂ -

Le A 23 009

-CH ₂

Cl

CH

CH ₃

H> CH ₃ CH ₃

CH ₃

C ₂ H ₅

-CH ₂ CH ₂ CH ₃ -CH ₂ CH ₂ CH ₂ CH ₃

-CH-C ₂ H ₅ CH ₃

-CH ₂ -CH (CH ₃ ) ₂ -C (CH ₃ ) ₃

-CH- (CH ₂ ) ₂ -CH ₃ CH ₃

-CH-CH (CH ₃ ) ₂ CH ₃

- (CH ₂ ) ₅ -CH ₃ -CH ₂ -CH = CH ₂

-C = CH-C ₂ H ₅ I CH ₃ EPO COPY

Table 1 (continued) Example No. RR ¹

1-243 CL ₂ CH- CH ₃ CH ₂ CH ₂ -1-244 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-245 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

H ₃

CH ₃

1-234 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-235 CL ₂ CH- CH ₃ CH ₂ CH ₂ -1-236 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-237 .CL ₂ CH- CH ₃ CH ₂ CH ₂ -1-238 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-239 CL ₂ CH- CH ₃ CH ₂ CH ₂ "

1-240 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-241 CL ₂ CH- CH ₃ CH ₂ CH ₂ -

1-242 CL ₂ CH- CH ₃ CH ₂ CH ₂ - -CH ₂ -C = CH ₂

CH ₃

CL

■ α O

1-246 CL ₂ CH- (CH ₃ ) ₂ CH- -CH (CH ₃ ) ₂ 1-247 CL ₂ CH- (CH ₃ ) ₂ CH- -CH ₂ CH ₂ CH ₂ CH ₃ 1-248 CL ₂ CH- (CH ₃ ) ₂ CH- -CH-C ₂ H ₅ CH ₃ 1-249 CL ₂ CH- (CH ₃ ) ₂ CH- -CH ₂ -CH (CH ₃ ) ₂ 1-250 CL ₂ CH- (CH ₃ ) ₂ CH- -CCH ₂ ) ₄ -CH ₃ Le A 23 009

EPOCOPY J

- ar -

Table 1 (continued)

Example No. RR ¹ R ²

1-251 Cl ₂ CH- (CH ₃ ) ₂ CH-

-CH- (CH ₂ ) 2 "CH ₃

1-252 CL ₂ CH- CCH ₃ ) ₂ CH- -CH ₂ -CH = CH ₂

1-253 CL ₂ CH- (CH ₃ ) ₂ CH- -CH ₂

1-254 CL ₂ CH- (CH ₃ ) ₂ CH-

1-255 Cl ₂ CH- IV-C ₄ H ₉ - -CH-C ₂ H ₅ CH ₃ 1-256 Cl ₂ CH- 11-C ₄ H ₉ - -CH ₂ -CH (CH ₃ ) ₂ 1-257 CL ₂ CH- nC ₄ H ₉ -C (CH ₃ ) ₃ 1-258 CL ₂ CH- nC ₄ H ₉ -CH ₂ -CH = CH ₂ 1-259 CL ₂ CH- nC ₄ H ₉ - -CH = CH-C ₂ H ₅ 1-260 CL ₂ CH- nC ₄ H ₉ - 1-261 CL ₂ CH- nC ₄ H ₉ - 1-262 CL ₂ CH- C ₂ H ₅ -CH-
CH ₃ -CH ₂ -CH (CH ₃ ) ₂ 1-263 CL ₂ CH- C ₂ H ₅ -C ₁ H-
CH ₃ 1-264 CL ₂ CH- (CH ₃ ) ₂ CH-CH ₂ - -CH ₂ -CH = CH ₂ 1-265 CL ₂ CH- (CH ₃ ) ₂ CH-CH ₂ - -CO-H 1-266 Cl ₂ CH- (CH ₃ ) ₂ CH-CH ₂ - -CO-CH ₃ 1-267 CL ₂ CH- (CH ₃ ) ₂ CH-CH ₂ - -CO-CHCL ₂ 1-268 Cl ₂ CH- (CH ₃ ) ₃ C- -CH = CH-C ₂ H ₅ 1-269 Cl ₂ CH- (CH ₃ ) ₃ C- -CH ₂ -CH ₂ -OH 1-270 Cl ₂ CH- CH ₃ - (CH ₂ ) ₅ - - (CH ₂ ) ₅ -CH ₃ 1-271 Cl ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ -CH = CH ₂ Le A 23 009

EPO COPY

JS '

Table 1 (continued)

Example No. R. R ¹ R2 1-272 CL ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ -C = CH ₂ CH ₃ 1-273 CL ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ -CH = N-OCH ₃ CL CL 1-274 JTL ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ A 1-275 CL ₂ CH- CH ₂ = CH-CH ₂ - -CH _{2> r} __ _rn

1-276 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-277 CL ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ -

1-278 CL ₂ CH- CH ₂ = CH-CH ₂ -

C ₂ H ₅

1-284 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-279 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-280 CL ₂ CH- CH ₂ = CH-CH ₂ - 1-281 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-282 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-283 CL ₂ CH- CH ₂ = CH-CH ₂ - -CH ₂ CH ₂ -N_

-CH ₂ - (C ^

CH ₃

CH ₃

-CH ^ ₁

Π Π

^ CH ₃

Le A 23 009

EPO COPY

- TfS table 1 (continuation )

Example No. R.

1-285 CL ₂ CH- CH ₂ = CH-CH ₂ "

-CH ₂ -C = CH ₂ Cl

1-286 CL ₂ CH- CH ₂ = CH-CH ₂ -1-287 CL ₂ CH- CH ₂ = CH-CH ₂ -

1-288 CT ₂ CH- CH ₂ = CH-CH ₂ -

C "3 1-289 CL ₂ CH- CH ₂ = C-

"CH ₃

CL ₂ CH- C ₂ H ₅ -CH = CH- CH ₃ 1-290 -CC = CH
I. CL ₂ CH- HC = C-CH ₂ - CH ₃ 1-291 CL ₂ CH- -CH ₂ -CN -CH ₂ -CH (0CH ₃ ) ₂ 1-292 CL ₂ CH- -CH ₂ CH ₂ -CN -CH ₂ -CN 1-293 CL ₂ CH- -CH ₂ CH ₂ -OH -CH ₂ CH ₂ -CN 1-294 CL ₂ CH- -CH ₂ CH ₂ -CL -CH ₂ CH ₂ -OH 1-295 CL ₂ CH- -CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ -CL 1-296 CL ₂ CH- -CH ₂ CH ₂ OC ₂ H ₅ -CH ₂ CH ₂ OCH ₃ 1-297 OH -CH ₂ CH ₂ OC ₂ H ₅ CL ₂ CH- -CH ₂ -CH-CH ₃ OH
I. 1-298 CL ₂ CH- - (CH ₂ ) ₂ OCOC ₂ H ₅ -CH ₂ -CH-CH ₃ 1-299 CL ₂ CH- - (CH ₂ ) 20C0CHCL ₂ - (CH ₂ ) ₂ OCOC ₂ H ₅ 1-300 CL ₂ CH- - (CH ₂ ) 20C00CH ₃ - (CH ₂ ) ₂ 0C0CHCL ₂ 1-301 CL ₂ CH- - (CH ₂ ) 2 ° C OSC ₂ H ₅ - (CH ₂ ) 20C00CH ₃ 1-302 CL ₂ CH- - (CH _{2) 2 3} 0C0NHCH - (CH ₂ ) 2OCOSC ₂ H ₅ 1-303 23 009 - (CH _{2) 2 3} 0C0NHCH Le A

EPOCOPY

Table 1 (continued)

Example No. RR ¹ R ²

1-304 CL ₂ CH-

1-305 CL ₂ CH-

1-306 CL ₂ CH-

1-307 CL ₂ CH-

1-308 _C L ₂ CH-

1-309 CL ₂ CH-

1-310 CL ₂ CH-

- (CH _{2) 2} 0C0N (CH ₃₎ 2 - (CH _{2) 2} 0C0N (CH _{3) 2}

■ (CH _{2) 2} 0C0NHC ₂ H ₅ ■ (CH _{2) 2} 0C0NHCH (CH _{3) 2}

- (CH ₂ ) ^ CONHCH ₂ Ch = CH ₂ - (CH ₂ ) ₂ OCO NH (CH ₂ ) 3 CH 3 - (CH ₂ ) ₂ OCONHCH ₂ CH = CH ₂

• (CH ₂ ) ₃ 0S0 ₂ CH ₃ - (CH ₂ ) ₂ 0S0 ₂ CH ₃

■ (CH ₂ ) ₃ NHC0CHCL ₂ - (CH ₂ ) ₃ NHC0CHCL ₂

1-311 CL ₂ CH- -CH ₂ OCH ₃

1-312 CL ₂ CH-1-313 CL ₂ CH-

1-314 CL ₂ CH-

-CH ₂ CH ₂ -SH

-CH ₂ CO-OC ₂ H ₅

CH ₃ -CH-CO-OCH ₃

fH ₃ 1-315 CL ₂ CH- -CH-CO-OCH ₃

CH ₃ 1-316 CL ₂ CH- -CH-CO-OCH ₃

1-317 CL ₂ CH-

CH ₃ -CH-CO-

OC ₂ H ₅

1-318 CL ₂ CH- -CH ₂

1-319 CL ₂ CH-

Le A 23 009

-CH ₂ -N ^ ₁

C ₂ H ₅

CH ₃

CH ₃

CH ₃

C ₂ H ₅

C ₂ H ₅ H

C ₂ H ₅ CH ₃

EPO COPY 0

- 35 -

Table 1 (continued) Example No. RR ¹

1-320 Cl ₂ CH- -CH-CH ₂ -OCH ₃

Cl CH ₂ 1-321 Cl ₂ CH- -C- = CH-COCH ₃

C «3

1-322 CT ₂ CH- -C = CH-COCH ₃

_f H ₃ 1-323 Cl ₂ CH- -C = CH-COCH ₃

1-324 CL ₂ CH- H ₃
-C = CH-COCH ₃ 1-325 CL ₂ CH- _f H ₃
-C = CH-COCH ₃ 1-326 CL ₂ CH- CH ₃
-C = CHCOOC ₂ H ₅ 1-327 CL ₂ CH- -U

1-328 CL ₂ CH- -CO-CHCl ₂

1-329 Cl ₂ CH-

1-330 Cl ₂ CH-

1-331 CL ₂ CH-

1-332 Cl ₂ CH-

Le A 23 009

CH ₃ CH ₃

C ₂ H ₅

CF ₃

CH ₃

-N = C

N (CH ₃ ) ₂ N (CH ₃ ) ₂

EPO COPY

Table l (continued) Example No. RR ¹ R ²

1-333 CL ₂ CH-

1-334 CL ₂ CH-

1-335 CL ₂ CH-

1-336 CL ₂ CH-

1-337 CL ₂ CH-

1-338 CL ₂ CH-

1-339 CL ₂ CH-1-340 CL ₂ CH-

1-341 CL ₂ CH-1-342 CL ₂ CH-

1-343 CL ₂ CH-Le A 23 009

CH ₃ -Q

CH ₃

-N

CH ₃ CH ₃

CH ₃

N J CH ₃

CH ₃

/ -V-CH ₃ -N) ^ CH ₃

CH

CH ₃

-N CH ₃ CH ₃

EPO COPY j§

Table 1 (continued).: - "..""-. * ... *" .. ": Example No. R Rl R * 4 * "Λ - _Ν ^ ₂ 3Α 1 8 1

1-356 CL ₂ CH-Le A 23 009

1-344 CL ₂ CH- Ν \

C ₂ H,

C ₂ H

f ~ \ c

1-345 Cl ₂ CH- -hf \ cH ₃

C ₂ H ₅

1-346 CL ₂ CH- -N / ~ C ₂ H ₅

1-347 CL ₂ CH-

CH ₃

1-348 CL ₂ CH- -N

C ₂ H ₅ 1-349 CL ₂ CH- CH ₃ (CH ₂ ) ₂ _

-Ö

1-350 CL ₂ CH- '-N ~~ YcH (CH ₃ ) ₂

> -CH ₂ 1-351 CL ₂ CH- _ _N

1-352 CL ₂ CH- -N

1-353 CL ₂ CH-

OCH ₃

1-354 CL ₂ CH- -NY

^N - ⁷ ^ OCH ₃

1-355 CL ₂ CH- -N

^ OC ₂ H ₅

" ^Ν Γ" Χ J

EPO COPY

Table 1 (continued) Example No. RR ¹ r2

1-357 Cl ₂ CH- 1-358 CL ₂ CH-

1-359 CL ₂ CH-

1-360 CL ₂ CH-

1-361 CL ₂ CH-

1-362 CL ₂ CH-

1-363 CL ₂ CH-

1-364 CL ₂ CH-

1-365 CL ₂ CH-

1-366 CL ₂ CH-

1-367 CL ₂ CH-

n '

CHjCH ₃

CH ₃ CH ₃ CH ₃ CH ₃

CH ₃ CH ₃

CO-CH ₃

"KZ / ⁿ

-N) - (CH ₂ ) ₃ - (N-CO-

CHCL;

NO \

-NO CH ₃ ^

.CH ₃ -NO

Le A 23 009

EPOCOPY J

GO

© O

r- (M he he

fit

(M ac

C 3 N 4J (U (0 4J

(U

IU Xl

L-

CQ

ν- / O = * -> O = CJ O "CJ

000000 O O O O O "cj

I I I I I I I I, 1 I I I

CJ (M

OO O Kl

X CJ (M

O Ό KI

I.
X
CJ
(M I.
X
CJ
(M I.
X
O
(M I.
X
CJ
fM I.
X
CJ
(M I.
X
CJ
(M I.
X
CJ
(M I.
X
CJ
(M I.
CJ
(M I.
X
CJ
(M I.
X
CJ
(M I.
X
CJ
(M (J ' CJ O CJ CJ CJ CJ CJ CJ CJ CJ CJ -370 K) -372 -373 -374 -375 -376 -377 -378 -379 -380 -381

I. I. X X CJ CJ (M (M CJ CJ CM Kl OO co AI Kl I. I.

O O

co

i-t HI

Table 1 (continued)

Example No. RR ¹ R ² \ iT> i '

1-384 Cl ₂ CH-

1-385 CL ₂ CH-

1-386 CL ₂ CH-

1-387 CL ₂ CH-

1-388 CL ₂ CH-

1-389 CL ₂ CH-

1-390 CL ₂ CH-

1-391 CL ₂ CH-

1-392 CL ₂ CH-

1-393 CL ₂ CH-

1-394 CL ₂ CH-

1-395 CL ₂ CH-

1-396 CL ₂ CH-

1-397 CL ₂ CH-

CH _3n

CHf

/ - ^ / - ν -N NO-CH ₃

CH ₃ F

-N N- (O) CL

O ₂ N

CH ₃ O -N N- (O)

, ^CF 3

, 0CH ₃

-N N-

-OCH ₃

-N N- (O)

C ₂ H ₅ O

r— \

-N N-

■ Ν NHU ^ -OCH ₃ CH ₃

Le A 23 EPO COPY

Table 1 (continued)

Example No. RR ¹ R ² blrU-

1-398 Cl ₂ CH-

1-399 Cl ₂ CH-

1-400 Cl ₂ CH-

1-401 Cl ₂ CH-

1-402 Cl ₂ CH-

1-403 Cl ₂ CH-

1-404 Cl ₂ CH-

1-405 Cl ₂ CH-

1-406 Cl ₂ CH-

1-407 Cl ₂ CH-

1-408 Cl ₂ CH-

1-409 Cl ₂ CH-

1-410 Cl ₂ CH-Le A 23 009 -N N-CO-CHCl ₂

CH ₃ CH ₃

N N-CO-CHCl ₂ CH ₃

-N N-CO-CHCl ₂

-N N-CH ₃

-N N-CO-CHCl ₂

k ¹

EPO COPY

- * ε - HS .1

Table 1 (continued) Example No. RR ¹ R ²

-N

1-411 CL ₂ CH-1-412 CL ₂ CH- 1-413 -CL ₂ CH-

1-414 CL ₂ CH- 1-415 CL ₂ CH-

1-416 CL ₂ CH-

1-417 CL ₂ CH-

1-418 CL ₂ CH-

1-419 CL ₂ CH-

1-420 CL ₂ CH- Le A 23 009

-N

CH ₃

-N

CH ₃

CH ₃ CH ₃

CH ₃

CH ₃ CH ₃

-N Λ-CHs

copy

Table 1 (continued) . R. H CH ₃ r2 t ^ η 1 3418167 Example No. CL ₂ CH- H CH ₃ - ^N -r2 1-421 CL ₃ C- H C ₂ H ₅ -CH ₂ -CH = CH ₂ CH ₃ ^ CH ₃
-N ^^ - CH ₃ 1-422 CL ₃ C- H -CH ₂ CH ₂ -Br 1-423 CL ₃ C- CH ₃
-CC ₂ H ₅
CN 1-424 CL ₃ C - -CH ₂ -NHCOCH ₂ CL 1-425 CL ₃ C- CH ₃ 1-426 CL ₃ C- -CH-C = CH
I.
CH ₃ 1-427 CL ₃ C- -CH ₂ CH ₂ CH ₂ CH ₃ 1-428

1-429 CL ₃ C- -CH ₂ CH ₂ CH ₃ -CH ₂ CHpCH ₃

1-430 CL ₃ C- -CH (CH ₃ ) ₂ -CH (CH ₃ ) ₂

1-431 CL ₃ C- -CH ₂ CH (CH ₃ ) ₂ -CH ₂ CH (CH ₃ ) ₂

1-432 CL ₃ C- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-433 CL ₃ C-

1-434 CL ₃ C- H CH ₃ -CC = CH
1 1-435 Br ₃ C- CH ₃ H CH ₃ -C-CN 1-436 Br ₃ C- H CH ₃ -CH ₂ -CH = CH ₂ 1-437 Br ₃ C- Le A 23 009

" ^N C_y

Table 1 (continued) Example No. RR ¹ R

R ¹

1-438 Br ₃ C-CH ₃

-CH-C = CH

1-439 Br ₃ C- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ CH ₃

1-440 CL-CH- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃
1-441 -GL-CH- -CH ₂ -CH = CH ₂ -CH ₂ -CO-CH ₃

CH ₃

1-442 CL

-CH- -

CH ₂ -CH = CH ₂ -CH ₂ -CH = N-OCH ₃

CH ₃ CH ₃

-CH ₇ -C = NC

1-443 CL-CH- -CH ₂ -CH = CH ₂ -CH ₂ -C = N-OCH ₃

CH ₃

1-444 CL-CH- -CH ₂ -CH = CH ₂ -

1-445 CL-CH- -CH ₂ -CH = CH ₂ -CH ₂ - ^ \

CH ₃

1-446 CL-CH- -CH ₂ -CH = CH ₂ -

CH ₃ 1-447 CL-CH- -CH ₂ -CH = CH ₂

* ³

CH ₃ I.
1-448 CL-CH-

CH ₃

1-449 CL-CH-

CH ₃

1-450 CL-CH-

CH ₃ 1-451 CL-CH-

CH ₃ CH;

-CH-COOCH ₃ - (O) CH ₃

-O

CH ₃ ,

CH ₃

CH ₃

Le A 23 009

EPO COPY Ά

Tabel 1 (continued) 45 -Wa.- .. ... CH? " 3418167 H3 Example No. RR ¹ R2 1-452 CH ₃
CL-OH- _
CH *

1-454 CH ₃
CL-CH- 1-45 5 CH ₃
Cl-CH- 1-45 6 CH ₃
Cl-CH- 1-45 7 CH ₃
CL-CH-

"5

1-45 8 CL-CH-

1-45 9 CH ₃
CL-CH- 1-460 Γ ³
CL-CH- 1-461 Γ
CL-CH- 1-46 2 Γ ³
CL-CH- 1-46 3 CH ₃
CL-CH- Le A 23 009

H ₃

-T) -CH ₃

CH ₃

CH ₃

-N

OC ₂ H ₅

OC ₂ H ₅

-oö -oö

CH
-N

-N N-CH ₃

-N N-COOC ₂ H ₅

EPO COPY

CO τ- OO

τ- IM CC CC

CJ CJ CJ

Nl I Nl I

XX XX

υ— υ ο - υ

I I

O Nl O Nl

U XUX

O "OOO Ό

ι σ> (M
CC I. Nl I Nl I Ni rvj -46 I. Nl I Nl I Nl I Nl I Nl I N) I Nl I C. . '\ X X X X X X Nl (M X X X X χ χ X X X X X X X X 3 U U O U U-U X X U-U U-U U-U U-U U-U υ— υ U-U N N) I I. L. I.
1 1 I. I. I. ^ ₁ I. ■ Ρ X X O U I " I. U U U U O U U CU O - O t U m «- I. ΙΛ VO O CM NN <r ΙΛ CC U I. ? 00 -46 sr -47 -47 I. -47 : -47 ο -46 Lu .3. -46 r-i Q) cc »Η r-i
f [\ » W.
Xi
W. L.
Z sp.l

CTl O O

(N

Q) ηΊ

Example No. RR ¹ r2

Cl-CH ₂ CH ₂ - - H CH ₃ 1-476 I.
-C-C = CH CL-CH ₂ CH ₂ - CH ₃ CH ₃ 1-47 7 CL-CH ₂ CH ₂ - -CH ₂ -CH = CH ₂ -CH-C = CH 1-47 8 CL
ι -CH ₂ -CH = CH ₂ CH ₃ -C- -CH ₂ -CH = CH ₂ 1-47 9 CL -CH ₂ -CH = CH ₂ Br
I. CH ₃ -CH- H CH ₃ 1-480 -CC = CH
I. Br
I. CH ₃ CH ₃ -CH- CH ₃ CH ₃ 1-48 1 Br -CH-C = CH CH ₃ -CH- -CH ₂ -CH = CH ₂ 1-48 2 F F
I I -CH ₂ -CH = CH ₂ I /
F ₃ CCC-
I I -CH ₂ -CH = CH ₂ 1-48 3 I ι
F F -CH ₂ -CH = CH ₂

1-48 4 BrCH ₂ CH ₂ CH ₂ -H -SO ₂ CL

1-485 f
Br-C-
I. H -CH ₂ -CH = CH ₂ CH ₃
-C-C5CH 1-486 CH ₃
CH ₃
I.
Br-C- -CH ₂ -CH = CH ₂
CH ₃ C ₂ H ₅ CH ₃
-CH ₂ -CH = CH ₂ 1-487 Br- (CH ₂ ) ₅ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ 1-488 HO-CH ₂ - C ₂ H ₅ 1-489 NC-CH ₂ - -CH ₂ -CH = CH ₂ Le A 23 009

EPO COPY

Example No. RR ¹ R ²

1-490 NCO-CH ₂ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

H -C-C = CH

^CH 2-CH ₃

aV Γ ³

(Υ CH ₃ -CH-C = I

N— f CH -.-

1-493 (Y -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

^ - ^J CH ₂ -

1-494 <Y CH ₃ "" -CH-C = CH

^N —'TH ₂ CH ₂ -

1-495 (Y -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

^N - ' CH ₂ CH ₂ -

1-496 ( X CH ₃ -CH-C = CH

^N ' CH ₂ CH ₂ -

1-497 / y -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-498 CH ₃ OCH ₂ CH ₂ - -C ₂ H ₅ -C ₂ H ₅

CHCL ₂

1-499 HO-CO-CH ₂ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CHCL ₂

CCL ₃

1-500 HO-CO-CH ₂ CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CHCl ₂

C ₂ H ₅ S _x

1-501 CH- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

C ₂ H ₅ S '

Le A 23 009

copy m

Table 1 (continued) Example No. RR ¹

1-502

-SZ

1-503 1-504

1-505

1-506

1-507 1-508

1-509

1-510 1-511

-CH ₂ - CH ₃

-CH ₂ - -CH ₂ -CH = CH ₂

-CH-

_C H-

CH ₃

CL

OCH ₃ -CH-

-CH-

Cl • CH-

ΪΗ-

CH ₃ -CH ₂ -CH = CH ₂

-CH-C = CH

-CH ₂ -CH = CH ₂

-CC = CH CH ₃ CH ₃ , CH = CH-CO-C (CH ₃ ) ₃

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

C-C = CH

CH ₃

CH-C = CH CH ₂ -CH = CH ₂

1-512

CL-

CH- -CH ₂ CH = CH ₂ -CH ₂ -CH = CH ₂

1-513 CL-Q) -S-CH ₂ - η TTl H

-CH ₂ -CH (CH ₃ ) CN |

-C-CN CH ₃

Le A 23 EPO COPY

Table 1 (continued) Example No. RR ¹

1-515 CH ₃ -CO-CH ₂ -

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-516 CH ₃ COOCH- H

1-517 CH ₃ CO-CH-H

1-518 CL ₂ CH-C -CH ₂ -CH = CH ₂

0-CH ₂ -

CLClCLCL till 1-519 C = C-C = C-C = O

CL

-CH ₂ -CH = CH ₂

CH ₂ -

1-520 CH ₃ O-CO-CH ₂ CH _{2 -H}

1-521 (CH ₂ = CH-CH _{2) 2} N

-CH ₂ CH = CH ₂

CH ₂ -

CH ₃

1-522 HC = C-C-NHH

CH ₃ CO

C ¹ H ₂ -

CH ₃ CH ₃ Il 1-523 HC = C-CH -N CH ₃

t = 0 CH ₂ -

CH ₃

-C-C = ^

CH ₃

CH ₃ ι

-C-CN I CH ₃

-CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂

CH ₃ I _

CH ₃ -CH ₂ -CH = CH ₂

CH ₃

-CC = CH CH ₃

CH ₃ -CH-C = CH

1-524 (CH ₂ = CH-CH ₂ ) ₂ n | -CH ₂ CH = CH ₂

C = O

CH ₂ -

-CH ₂ -CH = CH ₂

Le A 23 009

Table 1 (continued) Example No. R.

-CH ₃

CH ₃ -CH -CSCH

1-525 HC = C-CH-NC-CCH ₂ ) ₂ -

CH ₃ η

1-526 CCH ₂ = CHCH ₂ ) ₂ NC-CCH ₂ ) ₂ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ CH ₃ CH ₃

1-527 HC = C-CH-NCC CH ₂ ) ₃ - -CH ₃ -CH-C = CH

CH ₃

9
1-528 CH ₂ C = CHCH ₂ ) ₂ NC-CCH ₂ ) ₃ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

-CC = CH I
CH ₃

f CH ₃

1-529 HC = C-C-NH-C-C-II

CH ₃ CH ₃

9i

1-530 (H ₂ C = CHCH ₂ ) ₂ NCC-

CH ₃

1-531 HC

CH ₃ CH ₃

= C-CH-N-C-C-

CH ₃ CH ₃ 9

CH ₃

1-532 HC = C-CH-NC-CCH ₂ ) ₄ -CH ₃

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

-CH ₃

-CH ₃ CH ₃ -CH-C = CH

CH ₃

-CH-C = CH

1-533 CCH ₂ = CHCH ₂ ) ₂ NC-CCH ₂ ) ₄ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

CH ₃

1-534 HCrC-C-NH-C-CH ₂ -C-CH _{2 -H}

CH ₃

CH ₃ CH ₃

-CC = CH I
CH ₃

1-535 HC

V ^s 9

HC-CH-NCI CH ₃

CH ₂ -O-CH ₂ - -CH ₃

1-536 (CH ₂ = CHCH ₂ ) ^ - C-CH ₂ -O-CH ₂ -CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-537 CCH ₂ = CHCH ₂ ) ₂ NS-CH ₂ - -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

Le A 23 009

EPO COPY

- ■ se -SS

Table 1 (continued) Example No. RR ¹

1-538 CH ₂ = CH-H

1-539 CH ₂ = CH-CH ₃

1-540 CH ₃ -CH = CH-

-C-CSCH CH ₃

-CH-C = CH

CH ₃

£ -C CH ₃

1-541 CH ₃ -CH = CH-

CH ₃ 1-542 CH ₂ = C-

1-543 CCH ₃ ) ₂ C = CH-

1-544 (CH ₃ ) ₂ C = CH- -CH ₃

1-545 CH ₃ -CH = CH-CH = CH-H

-CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂ CH ₃

-CC = CH I CH ₃

CH ₃ -CC = CH

CH ₃

CH ₃ -CH-C = CH

CH ₃ -CC = XH

CH ₃

-CH ₃

1-546 CH ₃ -CH = CH-CH = CH- -CH ₂ -CH = CH ₂

CL

1-547 CL-CH = C-CH ₃

1-548 HO-C = C-H

I COOCH ₃

-CH ₂ -CH = CH ₂

CH ₃ -CH-C = CH

CL

1-549

1-550

-CH = CH-

-CH = CH-

-C (CH ₃ ) ₃

CH ₃ I.

-C-CN I CH ₃

Le A 23 009

copy m

Table 1 (continued) Example No. RR ¹

1-551

CH = CH-

CH ₃ CH ₃ -CH-C = CH

1-552 ^ -CH = CH- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-553

CH = CH-H

1-554 ^ -CH = CH- -CH ₂ -CH = CH ₂

1-555 F - @ - CH = CH- -CH ₂ -CH = CH ₂

CL

1-556 ^ -CH = CH- -CH ₂ -CH = CH ₂

1-557 CH ₃ - ^> - CH = CH-H

CH ₃ O _n

1-559 C ^ -CH = CH-H

CH ₃ O

1-560

CH ₃

CH = C-

1-561 CL-Q) -O-CH = CH-H

CL I 1-562 CL ₂ C = C-

CH ₃ C-CN CH ₃

CH ₂ -CH = CH ₂ CH ₂ -CH = CH ₂ CH ₂ -CH = CH ₂

-CC = CH CH ₃

1-558 CH ₃ - ^ - CH = CH- -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃ C-C ^ CH CH ₃

CH ₃ C-CN CH ₃ CH ₃ C-C = CH CH ₃

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

Le A 23 009

EPO COPY

Table 1 / continued) B sp. R r1

tv. H
1-563 PX

[X "

1-565 [> <"

.-569 Q (

CH ₃

-CH ₂ -CH = CH ₂ H

CH ₃ -CH ₂ -CH = CH ₂

CH ₃

-CC = CH CH ₃ CH ₃ HC = CH

-CH ₂ -CH = CH ₂

C-CN CH ₃

CH ₃ -CC = CH

CH ₃

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

CH ₃

C-C = CH I

CH ₃

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

C-C = .CH

CH ₃

-C-CN

CH,

Le A 23 009

EPO COPY

- 53-

- Si

• 34Ί8167

Table 1 (continued) Example No. R.

1-574

-C-C = CH

CH ₃

-N (CH ₂ CH = CH ₂ ) ₂

1-575 | CH ₂

1-576 1-577 1-578

1-579 1-580

1-581 F-1-582 F-

1-583 1-584

1-585 CL-

1-586 CL-

1-587 CL- <Le A 23

CL CL -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

-CH ₂ -CH = CH ₂ H

CH ₃ -CH ₂ -CH = CH ₂

H -CH ₂ = CH = CH ₂

CH ₃ -CH ₂ -CH = CH ₂

CH ₃ -CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂ fH ₃

-CC = CH I CH ₃

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

fH ₃

-C-CN

CH ₃

-CH ₂ -CH = CH ₂

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

CH ₃

-C-CSCH I.
CH ₃

CH ₃

-CH-C = CH

-CH ₂ -CH = CH ₂

EPO COPY

. S3

Table l (continued) Example No. RR ¹

3 A1 81 6

R ²

1-588 1-589 1-590 1-591

1-592 1-593

CL

Br Br

CL

1-594 CL- *

CL

1-595 CL-Q-CL

1-596 CL CL

1-597

: h ₃

1-598

CH ₃ . 1-599 O-

CH ₃

-CH ₃

-CH ₂ -CH = CH ₂ H

-CH ₃ H

-CH ₃

-CH ₃

-CH ₃ -CH ₃ -C (CH ₃ ) ₃ CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

-CC = CH I
CH ₃

CH ₃ -CH-C = CH

CH ₃ I.

-CC = CH I
CH ₃

CH ₃ -CH-C = CH

, CH = CH-CO-C (CH ₃ ) ₃

CH ₃ -CH-C = CH

CH ₃ - -CC = CH CH ₃ CH ₃ -CH-C = CH

CH ₃ I.
-CH-CECH

1-600

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

Le A23 EPOCOPY

- ¥ Γ Table 1 (continued)

Example No. RR ¹

-

1-601 CH ₃ -

1-602 CH ₃ - <1-603 CH ₃ H

OCH ₃

1-604

, OCH ₃ 1-605

1-606 CH ₃ O-

1-607 CH ₃ O-

CH ₃ O.

1-608 CH ₃ O- (O) -CH ₃ O '

1-609

CH ₃ O

1-610

1-611

1-612

1-613

O ₂ N.

CH ₃

-CH ₂ -CH = CH ₂

-CH ₃

-CH ₃ -CH ₂ -CH = CH ₂

-CH ₃ -CH ₃

-CH ₃ -CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂

CH ₃ -CC = CH

CH ₃

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

CH ₃

CH ₃

CH ₃ -CH-C = CH

CH ₃ I.
-CH-C = CH

-CH ₂ -CH = CH ₂

CH ₃ -CH-C = CH

CH ₃

-CH-C =

CH ₃ -CH-C = TCH

-CH ₂ -CH = CH ₂

CH ₃

-CC-CH I ~ CH ₃

-CH ₂ -CH = CH ₂

Le A 23 EPO COPY

-

Table 1 (continued) Example No. RR ¹

1-614 O ₂ NH

1-615 O ₂ N-1-616

1-617

0OH

1-618

1-619

COOH

..COONa

1-620 (Q-

CH ₃

-C-C:

CH ₃

CH ₃

CO-NH-C-Cr = CH

1-621 (O) ™ ³ H.

/ CH ₃

1-622

^ CO-N

CH-CS-CH -CH ₃

CH ₃

/ CH ₃ , CO-N _x

1-623 (Γ) \ CH-C = CH ^

^X 'CH ₃

CH ₃ -CC = CH

CH ₃

CH ₃ -CH-C = CH

-CH ₂ -CH = CH ₂

-C-C = CH

-CH ₃ -CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

H -C-C = CH

Your _3rd

CH ₃

H -C-C = CH

CH ₃

CH ₃ .

-C-C = -CH »

CH ₃ CH ₃

-CH-C = CH

C « ₃

-CH-C = CH

Le A 23 EPO COPY

Table 1 (continued) Example No. RR ¹

1-624

CO-N (CH ₂ CH = CH ₂ ) 2

-CH ₂ -CH = CH _{2 O = C} 'N (CH ₂ CH = CH ₂ ) ₂

1-625 (Q

-CH ₂ -CH = CH ₂

1-626 ClCH ₂ -CO-NH-

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃ I.

-CC = CH I CH ₃

(CH ₂ = CHCH ₂ ) ₂ N- (1-627 \ Q / ~ "CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

(CH ₂ = CHCH ₂ ) ₂ NC CH ₃ 0 ) - ^H fH ₃ Vs H
V
A, -C-CN
I.
CH ₃ i ^H3 ι? (I Il NC-C-NH-C " ⁰ -CH ₂ -CH = CH ₂ 1-628 NC-C-NH-C H -CH ₂ -CH = CH ₂
CH ₃ CH ₃ 0 -C-C = CH ta CH ₃ 1-629 23 009 -CH ₃ CH ₃ 1-630 -CH ₂ -CH = CH ₂ -CH-C = CH -CH ₂ -CH = CH ₂ 1-631 1-632 Le A

EPO COPY

Table 1 (continued) Example No. RR ¹

- 60

- S3

1-633 OL

1-634

-CH ₃

CH ₃

-CC = CH CH ₃

CH ₃

-CH-C = CH

1-635

1-636

C3CH CH ₃ -C-CH ₃

HN-C II O

-CH ₂ -CH = CH ₂

N- ^ H

-CH ₂ -CH = CH ₂

CH ₃

-C-C = CH I

CH ₃

1-637

(CH ₂ = CHCHg) ₂ NC O

-CH ₂ -CH = CH ₂ -CHg-CH = CH ₂

1-638 Cl-CH ₂ CH ₂ O- -Chg-CH = CHg

1-639 ^ CHCH ₂ O- -CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

1-640 CH ₃ -C = X-CH ₂ O- -CHg-CH = CH ₂

-CH ₂ -CH = CH ₂

1-641 t

1-642 C ₂ H ₅ O-1-643 C ₂ H ₅ OC

-CH ₂ -CH = CH ₂

-CH ₃ -CH ₂ -CH = CH ₂

-CHg-CH = CH ₂

CH ₃

-CH-C = CH

-CH ₂ -CH = CH ₂

Le A 23 009

EPO COPY

- ef - SH ': j-. ·: j »·. · X L.

Table 1 (continued) · - · - · "* · - * ··· *" ·· "^; * 3/1 D1C 7

Example No. RR ¹ R ²

Le A 23 009

1-644 HC = C-C-NH-C-H -C-C = CH

CH ₃ CH ₃

CH ₃ CH ₃ CH ₃

Il I

1-645 HC = C-CH-NC- -CH ₃ -CH-C =

Il
0

I -646 (CH ₂ = CH-CH ₂ J ₂ NC- -CH ₂ CH = CH ₂ -CH ₂ -CH = CH ₂

EPO COPY

The amides of the formula (I) which can be used according to the invention are known Cvergl.z.B. DE-OS 28 28 265 or DE-OS 32 28 007 or DE-OS 22 18 097).

They can be made by taking amines of the formula (III),

H-N (III)

in which

R ¹ and R ^{2 have} the meaning given above,

e.g. with Acy I chlorine of the formula (IV),

R-CO-Cl (IV) in which

R has the meaning given above,

optionally in the presence of an acid binder, such as Triethylamine, DimethyLbenzylamiη or pyridine, as well

15 optionally in the presence of a diluent such as methylene chloride or acetonitrile at temperatures between 0 ° and + 120 ° C. In this reaction, an excess of amine of the formula (III) used can also act as an acid binder at the same time. In this case the ¹

Addition of an additional acid binder.

The amides of the formula (I) which can be used according to the invention are, as already mentioned, suitable for improvement the crop plant tolerance of herbicidally active Heteroaryloxyacetamides of the formula (II).

Le A 23 009

EPO COPY

The herbicidally active hetero aryloxyactamides are generally defined by the formula (II). -

Herbicidal HeteroaryLoxyacetamid are preferably used of formula (II), in which

Het for an optionally singly or multiply, identically or differently substituted heterocycle of the formula r ^N Π ^N w— _M ^^^ ^N v ^N ~~ ^N

where X stands for oxygen or sulfur and where possible substituents are: Halogen, cyano, nitro, each straight chain or branched alkyl, alkoxy, alkylthio, alkylsulfonyl, A I ky I carbony I or A I koxycarbony I with 1 to 8 each Carbon atoms in the individual alkyl parts, respectively straight-chain or branched haloalkyl, haloalkoxy or HalogenaIkyIthiο with 1 to 6 each Carbon atoms and 1 to 9 same or different Halogen atoms, optionally single or multiply, identically or differently substituted by halogen straight-chain or branched dioxyalkylene and in each case optionally single or multiple identical or phenyl differently substituted by halogen, cyano, nitro, lower alkyl or lower haloalkyl, Phenoxy, phenylthio, benzyl, benzyloxy or benzylthio

25 and

R and R independently of one another for

in each case straight-chain or branched alkyl, alkenyl, Alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, phenylalkyl, Tetrahydrofuryla IkyL, alkoxy, alkenyloxy or Alkoxyalkoxy of up to 10 carbon atoms each in the individual alkyl, alkenyl or alkynyl parts and optionally 1 to 9 identical or different

Le A 23 009

EPO COPY

Stand halogen atoms, also for cycloalkyl, or Cycloalkenyl each having 3 to 8 carbon atoms or for each, possibly single or multiple, the same or differently substituted phenyl, naphthyl or Morpholinyl, where possible substituents are: halogen, cyano, nitro, as well as straight-chain ones or branched alkyl, alkanediyl, alkoxy, alkylthio, haloalkyl or haloalkoxy with each 1 to 4 carbon atoms and optionally 1 up to 9 identical or different halogen atoms, or at them

R ³ and R ^ together with the nitrogen atom to which they are attached, for each Is optionally mono- or polysubstituted, identically or differently substituted

15 PyrroIidinyI, Piperidyl, PerhydroazepinyL, Per-

hydroazocinyI, dodecamethyLenimino, morpholinyl, 1,3-thiazo LidinyI, 1,4-pi perazinyI, dihydro- or perhydroindolyl or dihydro-, perhydro- or tetrahydroquinolyI or -iso-quino LyI stand, where as substituents in-

20 questions come up: halogen, each straight

chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms, each doubly linked Alkylene or dioxyalkylene each having 1 to 4 carbon atoms or each optionally single or

25 multiple, identical or different due to halogen,

lower alkyl or lower alkoxy substituted Phenyl or benzyl.

It is particularly preferable to use herbicidal heteroaryloxyacetamides of formula (II), in which

Het for an optionally mono- to triple, identically or differently substituted heterocycle of the formulas ^N Π ^N NN • ^^ N- ^ N. NN

IL _x A. NA A PCV I

Le A 23 009

EPOCOPY β

where X is oxygen or sulfur and the following are possible as substituents: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, η- and i-propyl, n-, i-, s- and t-butyl , Methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy, methylthio, ethylthio, n- and i-propyIthio, n-, i-, s- and t-butylthio, methyl sulfonyI , EthyIsulfony I, n- and i-propylsulfonyl, n-, i-, s- and t-ButyIsulfonyI, acetyl, propionyl, methoxycarbony I, ethoxycarbony I, n- and i-propoxycarbonyl, trifluoromethyl, difluorochloromethyl, dichlorofluoromethy I, Trich , Chloromethyl, dichloromethyl. Pentafluoroethy I, HeptafIuorpropy I, trifluoromethoxy, trifluoromethylthio, dioxydifluoromethylene and each optionally one to three times identical or different by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl or trifluoromethyl substituted phenyl, phenoxy, phenylthio, benzyl, benzyloxy th i ο and

R ³ and R ^ independently of one another are methyl,

Ethyl, η- and i-propyl, n-, i-, s- and t-butyl, n- and i-pentyl, n- and i-hexyl, n- and i-octyl, n- and i-decyl, AlLyI, butenyl, propargyl, butynyl, pentynyl, Hexinyl, trifluoromethyl, trifluoroethy I, cyanomethy I, Cyanoethyl, methoxyethyl, ethoxyethyl, benzyl, phenylethyl, Tetrahydrofurylmethy L, methoxy, ethoxy, n- and i-propoxy, n-, i-, s- and t-butoxy, allyloxy, butenyloxy, methoxyethoxy. Ethoxyethoxy, cyclopropoxy, cyclohexyl, CycLoheptyl, CyclohexenyI, Morpholinyl or in each case one to three times, identically or differently substituted phenyl or naphthyl, where as Possible substituents: fluorine, chlorine, bromine, cyano, nitro, phenoxy, methyl, ethyl, η- and i-propyl, propanediyl, Methoxy, ethoxy, η- and i-propoxy, methylthio, Trifluoromethyl or trifluoromethoxy or those

Le A 23 009

EPO COPY

and R ^ together with the nitrogen atom to which they are bound, for one in each case possibly einbis triple, identically or differently substituted Remainder of the formula

-N

; -N J ; -N

CCH ₂ ) ₁₂ ;

■ N O; -N S; -N NH; -N

or

stand, with possible substituents: Chlorine, methyl, ethyl, η- and i-propyl, methoxy, ethoxy, n- and i-propoxy, and in each case optionally one to Phenyl or benzyl substituted three times identically or differently by fluorine, chlorine, methyl or methoxy.

In particular, the following compounds are general Formula (II) called:

Het - O - CH ₂ - CO - N

(II)

Le A 23 009

EPO COPY

Table example no. Het

-Vl-

II-2

II-3

CH ₃

CH ₃ -CH-

Jj M CH ₃ OCH ₂ CH ₂ - CH ₃ OCH ₂ CH ₂ -

IJL -O

-D

CH ₃ - ^

II-8 ^ y, N

Ct ⁰

Le A 23

-O

CH ₃ CH ₃

EPO COPY

Table 2 (continued) Example No. Het R ³

11-9

11-10 "« η ·; -ν

11-11

11-12 11-13 11-14

CL ^ f] N

CL-

CL

lime

11-15 11-16

11-17

CL

CL

CL-

K ₀ X

i-N k

11-18 N -X

CL

11-19

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

-N O

CH ₃

-N O

CH ₃

NO ₂ C ₂ H ₅ C ₂ H ₅ CH ₃ (CH ₂ ) ₂ - CH ₃ (CH ₂ ) ₂ - (CH ₃ ) ₂ CH-0- (CH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O (CH ₃ ) ₂ CH- CH ₃ O- C ₂ H ₅ -CH-

Le A 23 EPO COPY

Table 2 (continued) Example No. Het R ³

11-20 11-21 ^H " ²²

CL-

CL-

CL

CL

Π Ν

^π " ²⁵ 11-26

CL-

N _n Π

CL-

II-27 N I

11-28

11-29

CL

CL CL

Π-30

CH ₂ = CH-CH ₂ - CH ₂ -CH = CH ₂ -

CH ₃

CH ₃ -Q

"Ο

CH ₃

-N

■ α

CH ₃ CH ₃

-N O

CH ₃

CH ₃ (CH ₂ ) ₂ -

Le A 23 EPO COPY

Table 2 (continued) Example No. Het r3

CL

11-31

ⁿ " ³²

CL CL

»-33

CH ₃

CH ₃

CH ₃

CH ₃

C ₂ H ₅ -CH-

F ₃ C-CH ₂ "

-CH-C = CH

11-35

«-36

11-37

11-38

11-39

11-41

CL

Le A 23

CL CL

CL CL

CL Cl

CL CL.

Cl 'CL

CL

CL CL

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

C ₂ H ₅

C ₂ H ₅

- <H

CH ₃

CH ₃

CH

CH ₃ O-

C ₂ H ₅

(CH ₃ ) ₂ CH-

EPO COPY

- «τ- 7V

Table 2 (continued) Example No. Het R ³

^: 341816 /

11-42

CL

Xl

CL CL

CL CL

CH ₃

C ₂ H ₅

C ₂ H ₅

CH ₃ (CH ₂ ) ₃ -

F ₃ C-CH ₂ -

-( H

CL 11-45

CL

CL

11-46 ||

CL

CL

CL CL

CL CL

CL "

CL

11-50 []

Cl '

¹ N

^ V: - N

V N

17a

CL

Υ; N

CH ₃ (CH ₂ ) ₂ -

(CH ₃ ) ₂ CH-

(CH ₃ ) ₂ CH-

(CH ₃ ) ₂ CH-

C «3

C ₂ H ₅ -CH-

JH ₃ C ₂ H ₅ -CH-

CH ₃ (CH ₂ ) ₂ -

(CH ₃ ) ₂ CH-

(CH ₃ ) ₂ CH-O-

C ₂ H ₅ OCH ₂ CH ₂ O-

CH ₃ O-

CH ₂ = CH-CH ₂ -O-

Le A 23

copy m

Table 2 (continued) Example No. Het R ³

3% 1 * 8167

-N

11-52

11-53

11-54

11-55

11-56

11-57

11-58

11-59

11-60

11-61

CL

Cl CL-,

CL CL

CL CL

CL CL

.CL CL

CL CL.

CL CL

CL 'CL _>

Cl / CL

CL

Y; N

£ 1

(CH ₃ ) ₃ C-CH- C ₂ H ₅ OCH ₂ CH ₂ O-

-V H

-V H

- (H ^ C-CH ₂ -

CH ₂ -

CH ₂ -

CH ₂ = CH-CH ₂ - CH ₂ = CH-CH ₂ -

-V H

CH ₃ O-

C ₂ H ₅ OCH ₂ CH ₂ O-

- (J

-O

Le A 23

EPO COPY ft

Table 2 (continued) Example No. Het R ³

-N

11-62

11-63

11-6 A

11-65

11-66

11-67

11-68

11-69

CL

Cl 'CL

CL CL

CL 'CL.

CL 'CL

CL

α,

Cl 'CL

Cl CL

CL

-Ö

.CH ₃

-NC ₂ H ₅

CH ₃

CH ₃ -N

₂ H ₅ CH ₃

-N

CH ₃

CH ₃

-ο

11-70

CL

CL '

11-71

Cl Le A 23 -N

CH ₃ CH ₃

EPO COPY

Table 2 (continued) Example No. Het R ³

R ⁴ Ww. -Ν:

11-72

11-73

11-74

CL CL

CL CL

CL 'Ck

CL 'CL

■ ™

11-77

11-78

CL CL.

CL CL

sX

11-79

ν. L.

CH ₃

11th

11-80

CH ₃ -

/ ^ P

CH ₃

-N

-C °

-N O

CH ₃

-N N-CH ₂ -

-N N

-N N-

■ Tko)

CH ₃ O

Le A 23

EPO COPY

Table 2 (continued) Example No. Het R ³

-U

11-81

CL

NC. CL

11-82

II-82a Tj N

NC CH ₃

11-83

11-84

11-85

11-86

11-87

11-88

11-89

NC CH ₃

NC CH ₃

NC CH ₃

NC CH

NC CH ₃

NC

NC

Jl S A

CH ₃ OCH ₂ CH ₂ "CH ₃ OCH ₂ CH ₂ -

CH ₃

CH ₃

CH ₃

CH ₃ (CH ₂ ) ₃ -F ₃ C-CH ₂ - -CH-

, CH ₃

Le A 23

EPO COPY

Table 2 (continued) Example No. Het

- jer -

n-, o

11-91

CH ₃

NC CH ₃

nc '"

CH ₃

NC ^S CH ₃

NC " ^S -

11-93

> i N

^CH V-

11-94 JTTfJ

11-95

11-96

.CH ₃

NC CH ₃

NC CH ₃

NC CH ₃

NC CH ₃

11-97

11-98

11-99

NC CH ₃

11-100

NC

Le A 23

JuX

C ₂ H ₅

C ₂ H ₅

C ₂ H ₅

C ₂ H ₅ . C ₂ H ₅

CH ₃ (CH ₂ ) ₂ -

(CH ₃ ) ₂ CH-

(CH ₃ ) ₂ CH-

CH ₃ C ₂ H ₅ -CH-

CC ₂ H ₅ -CH- C ₂ H ₅

(CH ₃ ) ₂ CH- F ₃ C-CH ₂ -

-CH ₂ -

CH ₃ (CH ₂ ) ₃ - (CH ₃ ) ₂ CH-

C ₂ H ₅ OCH ₂ CH ₂ O-

-CH ₃

CH ₃ O-

CH ₂ = CH-CH ₂ - CH ₂ = CH-CH ₂ -

EPO COPY

Table 2 (continued) Example No. Het R ³

R *

'Cr *

CH

NC CH

11-102

11-103

11-104

CH ₃

11-106

11-107

CH ₃

N

NC CH

NC CH ₃

NC CH ₃

11-108 [|

NC 'CH ₃

11-109

11-110

NC CH

NC

V N

JCX

XH ₃

-N) -CH ₃

CH ₃

CHz

CH ₃

" ^N

-ν

-N

Le A 23

IEPO COPY

Table 2 (continued) Example No. Het R ³

- Tfi -

NC CH ₃

11-112

Xl

NC ^ö

CH ₃

11-113

CH ₃

CHrc

CH ₃ 11-114 Ti N

CH ₃

CH ₃ OC ^ SI! 0

11-115 ^CH 3

CCH ₃ ) ₂ CH0-

CH ₃

¹¹ ^ u X ~ J

CL 11-117>; - N

OC ₂ H ₅

CH ₃

-N V

CL

11-118

CH ₃

CL CL

Le A 23

EPOCOPY Μ

Example No. Het R ⁴

• -N.

11-119

^C Z ^H 5

Ν —Ν A

CH ₃

11-120

—N

(CH ₃ ) ₂ CH-

11-121 N-N

11-125

11-122 N-N

11-123

Ν — Ν i Il

11-124 Ν - Ν

N-N -D

CH ₃ C ₂ H ₅

CH ₃

-N

CH ₃

-OG

TT-1PA

11-127

11-128

N — N I Γ

N-N

CH ₃

Le A 23 009

EPO COPY

Table 2 (continued) Example No. Het r3

11-129

11-130 N-N

CH ₃ (CH ₂ ) ₃ x ⁵

11-131 N ~ N

(CH ₃ ) ₃ C

CH ₃

gh ''

R *

CH ₃

-N

11-132

CCH ₃ ) ₃ (

11-133 N N

^CH 3

11-134 11-135

(CH ₃ ) ₃ C

CCH ₃ ) ₃ C

X _s Jk

N N

Ί I

11-136 11-137

(CH ₃ ) ₃ C-

(CH ₃ ) ₃ C

N N

Il

N N

l I

11-138

(CH ₃ ) ₃ C

Le A 23

Ν — Ν CH ₃

C ₂ H ₅

CH ₃

-N

-N

C ₂ H ₅

rCH ₃

CH ₃ CH ₃

-N

EPO COPY ft

Table 2 (continued) Example No. Het R ³

11-139 N-N

F ₃ C

CH ₃

11-140, ^Ν , ~~ 7ί CH ₃

CH ₃ (CH ₂ ) ₃ -

-CH ₂ -

11-141 N-N

F ₃ CA

CH ₃

Π-142 Ν - N

F ₃ C

11-143

11-144

N - N

N N

F ₃ C

CH ₃

CH ₃

CH ₃ CH ₃

CL

CH ₃

11-145 N N

CH ₃

11-146 j}, J CH ₃

NO ₂

CF ₃

11-147

N N

CH ₃ -Q

NO ₂

11-148 N j} C ₂ H ₅

F ₃ C ^ S ^

Π-1Α9 Λ, 1 C ₂ H ₅

C ₂ H ₅

(CH ₃ ) ₂ CH-

Le A 23 009

Table 2 (continued) Example No. Het. r

R ⁴

R ³

-N

N N

N-N

11-150

CF ₃ '

ττ-ιςι ^{Ν Ν}

¹⁵ LI Il

CF ₃ - ^ S- ¹ N

11-153 ^Ν ~ >>

11-154

11-155

II-156

11-157

11-158

N - N

N - N

N-N

11-159
F. N-N
₃ CASA ~ Ν 11-160
F. Ν ~
₃ C ^ i Le A 23 009

C ₂ H ₅ -C ₂ H ₅ -CH ₃ (CHp) ₂ -

CH ₃

CH ₃ (CH ₂ ) ₂ -

CH ₃ (CH ₂ ) ₂ - CH ₃ O-

-O

CH ₃

-Q

C ₂ H ₅

- (T ^) - C ₂ H ₅

CH.
-NJ) -CH ₃

Table 2 (continued) Example No. Het R ³

11-161 r

F ₃ C ^

N-N

11-162 11-163

N-N

N-N

CH ₃ CH ₃

CHi

CH ₃

-O

11-164 11-165 11-166

N-N

N-N

N-N

CH ₃

-N

11-167

N - N

CH ₃

11-168 π µ C ₂ H ₅

C2H5

11-169 μ η CH ₃ (CH ₂ ) ₂ - CH ₃ (CH ₂ ) ₂ -

11-170

N-N

(CH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O-

11-171! Γ, ^Ν

CH ₂ = CH-CH ₂ - CH ₂ = CH-CH ₂ -

Le A 23

EPO COPY

Table 2 (continued)

11-17? CH ₃ ³

° ^2Hs

11-174 ^N -

LI

CH ₃ (CH ₂ J ₂ S - ^ S ^

11-176

-b

11-177

Ν — Ν

11-178

11-179

11 "W CH ₃ ""^

11-180 N-N

11-181 Ν—

(CH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O-

Le A 23

EPO COPY &

Table 2 (continued)

Example No., Het

11-182 Ν — Ν

CH ₃ SO ₂ - "" ^

CH ₃ C ₂ H ₅ -CH-

11-183

C ₂ H ₅ SO ₂

N-N CH ₃

, JLl. "

11-184

N-N CH ₃

11-185 N-N

11-186 N-N

11-187 Ν — Ν

11-188

11-189 Ν — Ν

11-190
i < Ν '
<rf —N
sA 11-191 11-192
< N-
1 ι —N Le A 23 , -Λ N-N 009

CH

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

C ₂ H ₅

C ₂ H ₅ CH ₃ O-

CH ₃ (CH ₂ ) ₃ - (CH ₃ ) ₂ CH-CH ₂ - F ₃ C-CH ₂ - - (H.

CH ₃

(CH ₃ ) ₂ CH-CH ₃ (CH ₂ ) ₃ -

EPO COPY

Table 2 (continued) Example No. Het

R ⁴

. -f * L

N-N S

11-193

11-194 N N

11-195

11-196

"N-N

UA

11-197 11-198 11-199

11-200

N-N ¹ A

N-N

N-N

11-201 11-202 11-203 Le A 23

N-N

N-N

C ₂ H ₅ -

C ₂ H ₅ - -CH ₂ -

CH ₃ (CH ₂ ) 3- (CH ₃ ) ₂ CH-CH ₂ -

(CH ₃ ) ₂ CH- (CH ₃ ) ₂ CH-CH ₂ -

(CH ₃ ) ₂ CH- (CH ₃ ) ₂ CH-0-

CH ₃ OCH ₂ CH ₂ - CH ₃ OCH ₂ CH ₂ -

-CH ₂ - HC = C-CH ₂ -

CH ₃

■ o

.C ₂ H ₅

EPO COPY

Table 2 (continued) Example No. Het -30

R ^A

, R ³

11-204

11-205

N-N

11-206

11-207

N - N

N N

N N

CH ₃

11-209

CH ₃

ix- «. J ~ l

CH ₃ . 11-212

CH ₃ .

11-213 * Μ

11-214

11-215

CH ₃ CH ₃
CH ₃

CH ₃
C ₂ H ₅

CH ₃
F ₃ C-CH ₂ -

C ₂ H ₅

-N VtH ₃

CH ₃ ^

-N

-N

(CH ₃ ) ₂ CH- (CH ₃ ) ₂ CHO-

(CH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O-

C "3

C ₂ H ₅ -CH- CH ₃ O-

Le A 23

EPO COPY

3418T67

Table 2 (continued) Example No. Het

- 31 '

11-216

11-217

Ύϊ — N N UL

11th

CH ₃ (CH ₂ ) ₂ ^ __ _N 11-218 n 'JJL

CH ₃ (CH ₂ ) ^ _n 11-219 K ₃ X

CH ₃ (CH ₂ ) _{2 N}

11-220

CH ₃ CCH ₂ > 2

11-221

11-222

11-223

(CH ₃ ) ₂ CH ₎ __ _N j

(CH ₃ ) ₂ CH _{) r} __ _N

11-224

11-225

^{<CH3) 2CH}

(CH ₃ ) ₂ CH,

11-228

CH ₂ = CH-CH ₂ - CH ₂ = CH-CH ₂ -

CH ₃ CH ₃

CH ₃ CH ₃ CH ₃ CH ₃

CH ₃

-CL

(CH ₃ ) ₂ CH- (CH ₃ ) ₂ CH0-

CCH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O-

C ₂ H ₅ -CH- CH ₃ O-

CH ₃

CH ₃ (CH ₂ ) ₃ -

CH ₃ IC ₂ H ₅ -CH-

F ₃ C-CH ₂ -HC = C-CH ₂ -

HC = C-CH-

Le A 23

EPO COPY

Table 2 (continued) Example No. Het R ³

<CH ₃ ) ₂ CH

X) L

- 11-230

11-231

-S '

(CH ₃ ) ₂ CH 11-232> j-N

11-234

ü-1

11-236

11-237

(CH ₃ ) ₂ CH

-S

11-238

(CH ₃ ) ₂ CH

11-239

(CH ₃ ) ₂ CHjj N

11-240

(CH ₃ ) ₂ CH.

Τ — Ν

<CH ₃ ) ₂ CH _N

CH ₃

CH ₃ CH ₃

CH ₃

C ₂ H ₅

C ₂ H ₅

-( H

-CL

CH ₃

C ₂ H ₅

(CH ₃ ) ₂ CH-

CH ₃ (CH ₂ ) ₃ -

CH ₃ (CH ₂ ) ₂ - CH ₃
C ₂ H ₅ -CH- (CH3) ₂ CH- (CH ₃ ) ₂ CH0- (CH ₃ ) ₂ CH- C ₂ H ₅ OCH ₂ CH ₂ O CH ₃
C ₂ H ₅ -CH- CH ₃ O-

11-241 CH ₃ O-CH ₂ CH ₂ - CH ₃ O-CH ₂ CH ₂ -

CH ₂ = CH-CH ₂ - CH ₂ = CH-CH ₂ -

Le A 23

_EP O COPY

Table 2 (continued) Example No. Het

R ³

^ _r4

(CH ₃ > ₂ CH

11-243 -α -ο

11-244

11-245

11-247

11-248

11-249 11-250

^ _N

N _ UL

^ S ^ -> ·

(CH ₃ ) ₂ CH

11-251 11-252

(CH ₃₅₂ CH. 11-253 [}

Le A 23

C ₂ H ₅

-N

■ α

ZW ₁ ,

CH ₃

^CH3

- {_) - CH ₃

CH ₃ CH ₃

-N

3A18167

Table 2 (continued) Example No. Het R ³

R ⁴

(CH ₃ ) ₂ CH

(CH ₃ ) ₃ C

(CH ₃ J ₃ C

11-254 11-255

11-256

<11-257

<Π-258

11-259 (

11-260

I 11-261 II-262 11-263

11-264 N

11-265

-CH ₃

N ⁷

vS

-CH ₃ -CH ₃

-CH ₃ -CH ₂

-CH ₃

-CH ₃

-CH ₃

-N

-N 0 N N-

CH ₃

CH ₃

Le A 23

EPO COPY

Table 2 (continued) Example No. Het R ³

-Sf-

-M-

11-266

11-267

11-268

11-269

-CH ₃

-CH ₃

^F3C ~ TN

11-270 ϊΓπ -C ₂ H ₅

F ₃ C

11-271

11-272

11-273

XX

F ₃ C ₁ T 11-274

F ₃ C-

11-275

F ₃ C 11-276 N

CLF ₂ C ^

CF-

CH ₃

-C ₂ H ₅ -C ₂ H ₅

-C ₂ H ₅

CH ₃

-CH ₃

-N

r <

CH ₃

-ö

C ₂ H ₅

CH ₃ -CH ₃

-O

Le A 23

Table 2 (continued) Example No. Het

11-278 Jm

11-280

CL ₂ FQ

11-282 Π-283 11-284 11-285

rr-

CL

11-286 Π-287

11-288 11-289

CL

CL

M CH ₃

_K Ü CH ₃

-CH:

-CH ₃

-CH:

CH ₃ '

-C ₂ H ₅

-CH ₂ -CH = CH ₂

CH ₃

CH ₃

> -CH ₃

CH ₃

O ₂

-O

Le A 23

EPO COPY

- 94 -

Table 2 (continued) Example No. Het r

R ⁴

x ^r

-N.

11-290 11-291 11-292

CL ₂ FC

CL ₂ FC

IS - <* »

-C ₂ H ₅

11-293 11-294 11-295 11-296

11-297

CL ₂ FC

CL ₂ FC.

CL ₃ C,

CL ₃

CL ₃ C>

■ Ν

CL ₃ C. 11-298 IT

11-299 "-300 11-301

CL ₃ C

CL ₃ C

-CH ₃ -CH ₃

-CH ₃

-CH ₃

-C ₂ H ₅

-CH ₃

- <H

CL

-CL

CH ₃

CH ^

Le A 23

EPO COPY

Table 2 (continued) Example No. Het R ³

11-302

11-303 11-304

11-305 11-306

11-307

CL ₃ C

CL ₃ C

11-308 11-309 ^CL 3 ^C

11-310 11-311

11-312

11-313 11-314

CL ₃ C

CL ₃ C.

CL ₃ C

Ti ^N

CL ₃ C

CL ₃ C,

CL ₃ C.

11-315

i \

Le A 23

-CH ₃

-CH ₃

-CH ₃

-C ₂ H ₅

-C ₂ H ₅

CH ₃

CH ₃

CH ₃ CH ₃
-C ₂ H ₅

<CH ₂ ) ₂ CH ₃ - (CH ₂ ) ₂ CH ₃ (CH ₂ ) ₃ CH ₃ - <CH ₂ ) ₂ CH ₃ CH-C ₂ H ₅
CH ₃ -OCH ₃ CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

CH ₃

CH ₃

■ 0

-O-

-σ

EPO COPY

Table 2 (continued) Example No. Het R ³

-N.

11-316

11-317

CL ₃ C

11-319

CH ₃ S.

CH ₃ S.

11-320 Π 7 *

CH ₃ S.

CH ₃ S

11-321 11-322

ΙΙ-323

11-324 11-325 11-326

11-327 11-328 11-329

Le A 23

ϊζ *

-CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂

CH ₃ I -CH-C ₂ H ₅ -CH ₃

CH ₃ -CH-C ₂ H ₅

"CH ₂ -CF ₃

-CH ₃

-CH ₃

-CH ₃

-CH ₃

-CH ₃

-C ₂ H ₅

-C ₂ H ₅

- (CH ₂ ) ₂ CH ₃ - (CH ₂ ) ₂ CH ₃

CH ₃

NO ₂

-C ₂ H ₅

■ ö

CH ₃

CH ₃

-O

-N

-O-CH (CH ₃ ) ₂

-OCH ₂ CH ₂ OC ₂ H ₅

-OCH ₃

EPO COPY

3 A1 81 67 -400

- 9 * Table 2 (continued y

Example No. Het H-330

11-331
11-332

11-333
11-334

CH ₃ S

CH ₃ S

CH ₃ S

CH ₃ S

CH ₃ S

11-337

CH ₃ S

-SÄ CH ₃ S._ _M

11-339

CH ₃ S.

^CH3S

^ K

11-341

-CH ₂ -

IJTlJ "CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

-O

-σ

CH ₃

CH ₃

-O

C ₂ H ₅

CH ₃

.CH ₃

-N

-O

CH ₃

Γ
-NO

Le A 23 009

EPO COPY Λ

Table 2 (continued) Example No. Het R ³

R ⁴

11-345

TT lit

11-346

II- »7 TT X / Q

11-348

11-349

11-350 11-351

11-352

11-342

: h ₂ s>, _M

11-343 - TF ^

-CH ₂ S _n

: h ₂ s

: h ₂ s>.,

TS

: h ₂ s

: h ₂ s.

-CH ₃

-CH (CH ₃ ) ₂ -OCH ₂ CH ₂ OC ₂ H ₅

-O

CH ₃

C ₂ H ₅

-O-

CH ₃

C ₂ H ₅

CH ₃

CH ₃

-N

-N

CH ₃

C ₂ H ₅

CH ₃

Le A 23

EPO COPY

Table 2 (continued)
Example No. Het R ³

11-353

* sÄ

11-355 Ν — N

-N

-N

-CH ₃ -CH ₃

11-356

N-N Il

11-357

\ l-N

11-358

N-N

CH ₃ -CH ₃ -CH-C ₂ H ₅

-CH ₃ -CH ₂ -C = CH

-CH ₃

CH ₃ -CH-C = CH

11-359

N - N ¹¹

"CH ₃

11-360

N-N Il

-CH ₃

Le A 23 009

EPO COPY

- MO '- *

Table 2 (continued) Example No. Het R ³ r4

N N

11-361

11-363 Γ "!?

-CH ₃

"-362 -. ^Ν Γ [) -

N ^ _n Λ -CH ₃

CH ₃

CH / ~ ^C 2 ^H 5 -C ₂ H ₅

11-364, ^Ν Γ ~ ί1

-CH (CH ₃ ) ₂

³⁶⁵

N N

U Il

- (CH ₂ ) ₃ CH ₃

II 366 ,,

"C ₂ H ₅ - (H.

11-367

-CCH ₂ ^ CH ₃ - (CH ₂ ) ₂ CH ₃

11-368

-CH (CH ₃ > 2 -OCH (CH ₃ ) ₂

A 23 009

EPO COPY Oi

Table 2 (continued) Example No. Het

R ³

11-369

N — N I / YY- -CH (CH ₃ ) ₂ -OCH ₂ CH ₂ OC ₂ H ₅

11-370

N N

11-371

N - N

I1-372

N - N CH ₃ I -CH-C ₂ H ₅

-OCH ₃

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

~ ^CH 2 ~ (O / -CH ₂ -CHCH

11-373

N - N Il

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

11-374

N-N ¹¹

11-375

N-N

¹¹ Il

11-376

N-N Il

«Ρ

■ ο

Le A 23 009

EPO COPY

Table 2 (continued)

0S - 16-2

Example No. Het

R ⁴

11-377

N-N

11-378

N-N -D

C ₂ H ₅

C ₂ H ₅

11-379

11-380

11-381

11-382

N N

"LL

N-N

ILA

N N

N N

P. 11-383 Cl ύ 11-384 N - N Le A 23 009

• α

CH ₃

CH ₃

CH ₃

N VcH ₃

■ -

C ₂ H ₅

-N

-O

ST

CH ₃ CH ₃

EPO COPY

- 3 * 3 "-

Table 2 (continued) Example No. Het R ³

-N

11-385

11-386

11-387

11-388

11-389

11-391

11-392

u — u J! V-

N-N

Il

N_

N-N

Ii> -

N-N '

N- N

CH ₃

N-N

Ii y

N-N

ΤΤ-70Π ^N ~ ^N v

LlSVO ι. A.

N-N

CH ₃

N- N

N-N

N- N

-CH ₃

CH ₃

-CH ₃

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

-CH ₃

-NO ₂ -CH ₃

- (CH ₂ ) ₃ CH ₃

-CH-C ₂ H ₅ CH ₃

-N

-N

N

Le A 23 009

EPO COPY

Table 2 (continued) Example No. Het r3

- 40? -

r. -N

11-393

11-394

Ν — Ν>

-N

ΝΝ

Il

N-N -CH ₃

NO ₂ -CH ₃

CH ₃

11-395

Il

N_N

11-396

N ^- N -N

(g) -NO ₂

-C ₂ H ₅

CH ₃ - (CH ₂ ) ₂ CH ₃ -CH-C ₂ H ₅

NO ₂

11-397

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

NO ₂

11-398

N ^- N.

Il> -

N-N

-CH ₂ - -CH ₂ -C = CH

11-399

NO ₂

(Q) -NO ₂ -O

CH ₃

11-400

Ν — Ν

Il

N_N

(Q) -NO ₂

Le A 23 009

-w-Ί r

Table 2 (continued) Example No. Het R ³

R * b ^ t /.

11-401

N ~ N yy \\ -

n-n '

_{TT / n} , 11-402

Ν — Ν

⁷ ^

11-403

-CH ₃

Π-40Α

-Ν N_N /

-CH ₃

"- ⁴⁰⁶

NN ^/ -CH ₃

rr

rry

11-407

11-408

[T

-no

-CH ₃ - (CH ₂ ) ₃ CH ₃

CH ₃ -CH-C ₂ H ₅

-C ₂ H ₅ -CH (CH ₃ ) ₂

Le A 23

EPO COPY

Table 2 (continued; Example No. Het R ³

_R 4

11-409

N_

CH ₃ I -CH-C ₂ H ₅

O-CF3

Ν "Ν 11-410 H ^

11-411

11-412

11-413

11-414

11-415

11-416

11-417

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

N ^- N

CF ₃

N ^- N

il '

Ν_Ν

O "

u_>

NN _x

NN N-N

CF ₃

ii

N_N

O-CF3

N ^- N _x

I! V

ν_ν /

'-CF ₃

Le A 23 009 CH ₃

-σ

CH ₃

C ₂ H ₅ -O-

C ₂ H ₅

CH ₃

-N) -CH ₃

-N

CH ₃

-N

-CH ₃

EPO COPY | §

Table 2 (continued) Example No. Het R ³

-N

11-418

11-420

11-421

11-422

11-423

11-424

Il V

N_N

N-N

N - N

Il ^v >

N -N

CL

CL

CL

CL

CL

CL

N ~ N

N-N

CL

Ν "Ν

π ^N

N-N

CL

CL

N_N

N ^- N

-C ₂ H ₅

-CH ₃

JN -CH ₃

CL- (OV CL

-CH (CH ₃ ) ₂

CH ₃ -CH-C ₂ H ₅

-N \

C ₂ H ₅

-N> -CH ₃ CH ₃

Le A 23 009

EPO COPY

Table 2 (continued) Example No. Het

11-425 Ij V

N-N

y-

-CH ₃

11-426

N-N

Il V

N_N ' -CH ₃

CL

CH ₃

11-427

NN

N_N

■ C2H ₅ - (CH ₂ ) ₃ CH ₃

11-428

Π-429

N-N

N-N

Il

"C ₂ H ₅ - <H

- (CH ₂ ) ₂ CH ₃ -CH-C ₂ H ₅

11-430

CL - <^ -

N-N _v

(I V

n__n /

"CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

11-431

N ~ N

Ii

N-N

" ^CH 2- (O) -CH ₂ -C ^ CH

11-432

Le A 23 009

EPO COPY

Table 2 (continued) Example No. Het R ³

- Jr & 9 -

I1-433 Κ

N-N

11-434 Ν "Ν

Ii y

N_N ⁷ CL- (H-CL

11-435 N-N

CL-O-CL

-N 0

CH ₃

11-436

w y

Nn '

-CH ₃

N-N

11-437 Κ

CL

-CH ₃

11-438

11-439

Ν "Ν

Ii \

N-N

N - N

Il

Ν — Ν

CL -CH ₃

11-440 yy

N ~ N

N-N

Le A 23 009 CH ₃ -CH-C ₂ H ₅

CH ₃

CH ₃

■ Ö

CH ₃

-N 0

CH ₃

EPO

Tabel 2 (cont s .. = _t -.zung) HO - - ι ' ^J
"CH-C ₂ H ₅ Example No. Het -CH ₃
-CF ₃ 11-441 N_N '

11-442 Il Λ—

"N-N ^

-CH ₃

N-N

Il ^

Ν - Ν CF ₃ ^ QhCF ₃

Ν "Ν N_N

-CH ₃

-C ₂ H ₅

N ~ N

Il "

N-N

- (CH ₂ ) ₂ CH ₃

CH ₃

-CH-C ₂ H ₅

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

Ν — Ν

H ^N

CH ₃

Le A 23 009

_E PO COPY

Table 2 (continued) Example No. Het R ³

-N

11-448

N ^- N

11-449 N-N

Il ^N N_N

11-450

NN

H y

N_N ⁷

11-451

N ^- N

Ii ^

N-N

11-452

NN

Il>) -

N- N

11-453

N ~ N

Ii

N-N

N ~~ N

Il

N-N

11-454

11-455 N-N

N_ N

"CH ₃ - (CH ₂ ) ₃ CH ₃

"CH ₃

-CH-

-CH ₃

-CH ₃ -CH-C ₂ H ₅

I. -CH-C = '

CH ₃

-O

CH ₃

-N

-N

CH ₃

CH ₃

Le A 23 009

copy

Table 2 (continued)

Example No. Het ~

R *

11-456

N-N

ii ^N

N-N

11-457 - Ν — f

Il

N_N

11-460

11-458 N-N

I! ^

N_N

11-459 N-N

II

N-N

N-N

N-N

11-461 N-N N-N CH ₃ -0-CL 11-462 iry
NN 11-463 N_n ' ^CH 3 -Q> -CL Le A 23 009

-C ₂ H ₅

- (CH ₂ ) ₃ CH ₃

-C ₂ H ₅

CH ₃ - (CH ₂ ) ₂ CH ₃ -CH-C ₂ H ₅

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

C ₂ H ₅

-Ö

CH ₃

C ₂ H ₅

EPO COPY

Table 2 (continued) Example No. Het R ³

-N

11-464

N_N

CH ₃ CH ₃

11-465

N-

11-466

N ~ N

Il "> -

N-N

11-467

N-N

CH,

II-468 [Γ ^Ν -

NN _CH3 -CH ₃

11-469

_Ν _ _Ν - _cH3 "CH ₃

-CH ₃ -CH-C ₂ H ₅

-CH-C = CH

-N

-N O

CH ₃

-CH ₃

11-470

CH ₃

-CH ₃

CH ₃

N-N

11-471

-C ₂ H ₅

Le A 23

_E P0 COPY Jf

Table 2 (continued) Example No. Het

- irtU -

-N

11-472

«■ ο

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

11-473

11-474

NN '-CH ₂ -

, CH ₃

Il

N-N

CH ₃

-CH ₂ -C = CH

C ₂ H ₅ '

11-475

N "" N

Il

N- \ Y

CH ₃

11-476

N-N

Cl- <

CH ₃

11-477

Il

N-N

CH ₃

11-478

11-479

N-N

N-N

Il

N_N

CH ₃

CH ₃ -N

-N

CH ₃

Le A 23 009

EPO COPY J

Table 2 (continued) Example No. Het R ³

- J ^ 5 -

11-480 11-481

11-482

11-483

11-484 11-485

JL

N YY-

11-487 11-488 11-489 11-490

11-491

11-492 11-493 Le A 23

■ ^Ο ^ ΐ

CH ₃

11-486 (grX CH ₃

CH ₃ CH ₃ CH ₃

CH ₃ CH ₃ CH ₃

CH ₃

-CH-C ₂ H ₅ -CH ₂ CH (CH ₃ ) ₂

CH ₃ °

CH ₃

- (CH ₂ ) ₃ CH ₃

-CH-C ₂ H ₅ -CH ₂ -CF ₃

-CH ₂ CH ₂ -CN

-CH ₂ -C = CH CH ₃

EPO COPY

Table 2 (continued)

Example No. Het

11-494

11-495 11-496 11-497 11-498

11-499

11-500 11-501

"- ⁵⁰² 11-503 11-504

-N

-CH ₃

-CH ₃

-CH ₃

-CH ₃

11-505 [Q.

CL

-Cl Br

-CH ₃ CL
CL- CL
> -CH ₃ 'CL
-CL
Kl -CH ₃ .CL
t -CH ₃ CL U CH _3x

Le A 23

EPO COPY J!

3A18167

Table 2 (continued) Example No. Het

-UP

I4rf

11-506 ΓΟΤ ~~ ίΐ "CH ₃

II-

11-509

11-510

ⁿ - ⁵¹¹

11-512

11-513
11-514

11-515
11-516

- ⁵⁰⁸ © Ca- - ^CH3 §CI - ^CH3

-CH ₃

-CH ₃ -CH ₃

-CH ₃ -CH ₃

-CH ₃

CH ₃

> -CH ₃

■ CH (CH ₃ ) ₂

CH ₃

CH ₃

CH ₃ CH ₃

CH ₃

CF ₃

CH ₃ O

CF ₃ CF ₃

CF ₃

Le A 23 009

EPO COPY

Table 2 ( Forfcssfτ..ng) Example No. Het r3

11-518

11-519

11-520
11-521

II-II-

11-524
11-525

11-526
11-527

Π-528
11-529
11-530

-CH ₃

-CH ₃

-CH ₃

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅

OCH ₃

OCH ₃ OCH (CH ₃ ) ₂

CH ₃ S

SCH ₃

-CH ₃

-CH ₃ -CH ₃

-CH ₃

-CH ₃ <O> -SCH ₃

-CH ₃

-CH ₃ Χ ()) - CL

CH ₃ '

-OCH ₃

-OCH ₂ CH ₂ OC ₂ H ₅

-CCH ₂ ) ₃ CH ₃

-CH ₂ CF ₃

Le A 23 009

EPOCOPY 1

. ^T «""» lle 2 (continued) E.g. Mr. .. Het _R 3

Π-532

11-533

11-535 11-536 11-537

11-540

- CH (CH ₃ ) ₂ -0-CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂ -OCH ₂ CH ₂ OCH ₃

-CH (CH ₃ ) ₂ -OCH ₂ CH ₂ OC ₂ H ₅

CH ₃
CH-C ₂ H ₅

CH ₃ -OCH ₃

OCH ₂ -CH = CH ₂

CHj-CHCCH ₃ );,

Le A 23 EPO COPY

Table 2 (continued) Example No. Het R ³

- 2-3-0 -

n-5.3

11-545 11-546

11-547 11-548

11-544 [Q.

, A

CH ₃ I.

-CH-C (CH ₃ ) 3 -OCH ₂ CH ₂ OC ₂ H ₅

C ₂ H ₅ -CH ₂ -CH-CCH ₂ ) ₃ CH ₃ -

C ₂ H ₅

CF ₃

-CF ₃

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

-CH ₂ CH ₂ OC ₂ H ₅ -CH ₂ CH ₂ OC ₂ H ₅

-CH ₂ CH ₂ OC ₂ H ₅ -OC ₂ H ₅

ils «(Qr ₁ " 11-550

11-551

11-553

11-554

-5S ₂ Car-n

QY-N

-CH ₂ -

-CHo-C = CH

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂ -0-CH ₂ -CH = CH ₂

-CH ₂ -CHHTCH -CH ₂ -C = CH

-OCH ₃

-OCH ₂ CH ₂ OC ₂ H ₅

Le A 23

EPO COPY ftl

Table 2 (continued) Example No. Het R ³

H-S56

11-557

11-558 11-559 11-560

.1-561

11-562

LQCl

ΠΓ ", Ϊ

CH ₃

C ₂ H ₅ CH _3n

■ Q

C ₂ H ₅

-ti) "CH ₃ CH ₃ ^> ^

CH:

-N

-O

11-563

CJl- ^N

11-564

-565 [O.

-N

CH ₃

CH ₃

CH ₃

CH ₃

CH? /

Le A 23 EPO COPY

Table 2 (continued) Example No. Het R ⁴

-Ν

11-566

11-568

1.-5 * 9

"- ⁵⁷⁰ (QDL

oca

11-572 11-573 11-574 11-575 11-576

CL

CL

CL

CL

CL

-CH ₃

"CH ₃

-CH ₃

-CH ₃

"CH ₃ -CH ₃

- (CH ₂ ) ₃ CH ₃

-CH ₂ -CF ₃

CH ₃

CH

-N

-N O

CH ₃

CH ₃

-N O

Le A 23

Table 2 (continued)

Example No. Het

Π-578 11-579

11-580 11-581 11-582

CL

CL

CL

K) TTI

-CH;

ΓΟΤΓί

11-583

11-584

11-585

Π-586

11-587

11-588

Le A 23

CL

CL

CL

CL

CL

CL

■ 0-CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂ -OCH ₂ CH ₂ OC ₂ H ₅

CH ₃

(CH ₂ ) 3CH ₃

CH ₂ -CH = CH ₂ -CH ₂ -CH = CH

-O

EPO COPY S

- ^Table 2 (continued)

Example No. Het _R 3

R ⁴ L Ή ,.

ⁿ - ⁵⁸⁹

11-590

CL

in ^N

11-591

-CL

CL 11-592

"-593" Tq] - n

CL 11-594

-ΟΓ7 / 1

11-595

CL

11-596 ⁿ " ⁵⁹⁷ 11-598

CL

CL '

-CH ₃

-C ₂ H ₅

- (CH ₂ ) ₃ CH ₃

- ^N O ~ ^C 2 ^H 5 -CH ₃

CH ₃

CH ₃

-N

-O

-N

-N

-N

CH ₃

■ Ο

Le A 23

COPY yy

Table 2 (continued) Example No. Het r3

11-600

11-601

11-602

11-603

11-604

CL

C CH ₃

.cco

CH ₃

• 0

CH ₃
11-605 Υ / ~ γ) ν

11-606

11-607

CH ₃

CH ₃

"CH ₃

-CH ₃

-CH ₃

-CH ₃

-CH ₃ -CH ₃

- (CH ₂ ) ₃ CH ₃

CH ₃

CH ₃

NO ₂

-C ₂ H ₅

t -ν '

CH ₃

11-608

CH ₃

11-609 VW! N

LU.

CH ₃

11-610

Le A 23 009

-C ₂ H ₅

-C ₂ H ₅

-C ₂ H ₅ -CH (CH ₃ ) ₂

EPO COPY

Table 2 (continued) Example No. Het

U3 i

CH ₃ 11-611 T / -V

CH ₃ 11-612 '

11-613

CH ₃

11-614

11-615

11-616

.CH ₃

CH ₃ V

CH ₃

CH ₃

-CH (CH ₃ ) ₂ -OC ₂ H ₅

-CH ₂ -

-CH ₂ -C = "CH

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

-N ^ -CH ₃

C ₂ H ₅

11-618

11-619

11-620

11-621

Le A 23

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

-N VCH ₃ CH /

Table 2 (continued) Example No. Het

- ν;

11-622 11-623 11-624

11-625

11-626

CH

CH

CH ₃

CL

-CH ₃

-O

-N

-N '

11-630 11-631

N H

-CH ₃

CH ₃ -CH-C ₂ H ₅

-CH ₂ -CH (CH ₃ ) ₂

-CH ₂ CH ₂ -

-CH-

11-632

-CH ₂

Le A 23

Table 2 (continued) Example No. Het _R 3

11-633

11-634

"-635

IOOl

^{: i} - ⁶³⁶ (OCX

11-637 11-638

11-639
11-640
11-641

11-642

11-644

-CH ₃

-CH ₃ -CH ₃

"CH ₃ -CH ₃

-CH ₃ -CH ₃

-CH ₃ -CH ₃ 1.2-β - _R 4

I CH ₃

-CH ₃

CH ₃ -CH-C ₂ H ₅

CH ₂ CH ₂ -CN

CH ₂ -CF ₃

CH ₂ -C = CH

-CH-C = CH

Le A 23 009

EPO COPY

Table 2 (continued) Example No. Het

WrI

11-645 11-646 11-647 11-648

11-649 11-650

11-651

11-652 11-653

11-654

11-655 11-656

11-657 Le A 23

-CH ₃ -CH ₃ -CH ₃ -CH ₃ "CH ₃

-CH ₃ -CH ₃

-CH ₃ "CH ₃

"CH ₃

"CH ₃ -CH ₃

-CH ₃

CL

CL

-O

CL CL

CH ₃

EPO COPY

Table 2 (continued) Example No. Het r3

11-658

11-659 11-660 11-661

11-662

11-663 11-664

11-665

11-666 11-667 11-668 11-669

-CH ₃ -CH ₃

-CH ₃

-CH ₃ -CH ₃

-CH ₃ -CH ₃

"CH ₃ -CH ₃

-CH ₃ "CH ₃

-CH ₃ -CH ₃

CH ₃ C ₂ H ₅

> -CH (CH ₃ ) ₂ CH ₃ . CH ₃

CH ₃ CH ₃

CH ₃ CH ₃

F ₃ C

CF ₃

CF ₃ CF ₃

CF ₃

CH ₃ O

OCH ₃

Le A 23

EPO COPY

Table 2 (continued) Example No. Het R ³

R *

11-671

11-672

11-673 11-674 IP-675

11-676

üci

S '

- N

II-677 OTjL.

11-678

I1-679 11-680 11-681

11-682

-CH ₃ -CH ₃

-CH ₃ -CH ₃ -CH ₃

-CH ₃ -CH ₃

"C ₂ H ₅

OCHCCH ₃ ) 2

CH ₃ S

SCH ₃

> -SCH ₃

CH ₃

CH ₃

NO ₂

C ₂ H ₅ -C ₂ H ₅ C ₂ H ₅ -CCH ₂ ) ₃ -CH ₃ C ₂ H ₅ -CH ₂ -CF ₃ C ₂ H ₅ '

Le A 23 EPO COPY

eat

Table 2 (continued) Example No. Het r3

11-683

11-684 11-685 11-686

11-687 11-688

LUl. ti

11-690

11-691 11-692 11-693 11-694 11-695 11-696

-C ₂ H ₅

-CH (CH ₃ ) ₂ -CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂ -0-CH (CH ₃ ) ₂ ■ CH (CH ₃ ) ₂ -0-CH ₂ CH ₂ OC ₂ H ₅

-CH (CH ₃ ) ₂

-CH (CH ₃ ) ₂

- (CH ₂ ) ₃ CH ₃

-CH-C ₂ H ₅ -CH ₂ -CH = CH ₂

CH ₃

-CH-C ₂ H ₅ -OCH ₃

CH ₃

-CH-C ₂ H ₅ -0-CH ₂ -CH = CH ₂

CH ₃ -CH ₂ -CH (CH ₃ )? -CH ₂ -CH (CH ₃ ) ₂

-CH ₂ CH (CH ₃ );

Le A 23 copy m

Table 2 (continued) Example No. Het R ³

-N.

11-697

11-699 11-700 11-701 11-702 11-703- 11-704 11-705 11-706

11-707 11-708 11-709

C ₂ H ₅ -CH ₂ CH (CH ₂ ) ₂ CH ₃ C ₂ H ₅ -CH ₂ CH (CH ₂₎ 3CH ₃

11-698 ly ^ sjL -CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

YY-

-CH ₂ - -CH ₂ - -CH ₂ - -CH ₂ -

-CH ₂ -C = CH

-CH ₂ -CH = CH ₂ -CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂ -OCH ₃

-O

CH ₃

Le A 23 copy m

- 234 -

- ^TABLE I (continued)

Ex. No. Het _R 3 _r4

11-71 ΐ

11-714

11-71

11-718

-N

- • Q-CH3 CH ₃

C ₂ H ₅

CH ₃
CH ₃

- CH ₃

-O

CH:

CH ₃

CH ₃

CH ₃

Le A 23 EPO COPY

Table 2 (continued) Example No. Het R ³

-N,

11-720

11-721

11-722

11-723

11-724

11-725 [QQ 11-726

11-727

11-728

-N (CH ₂ ) τ ο

"Ν> -CH ₃

CH ₃

Le A 23 EPO COPY Μ

Table 2 (continued) Example No. Het r3

11-729

11-730

-N.

-N

N O

11-732

11-733.

11-734

CL

-CH ₃

CL -CH ₃

-N O

CH ₃

-N

11-735 C ₂ H ₅ O

11-736 C ₂ H ₅ O

-CH ₃

-CH ₃

CH ₃ -CH-C = CH

11-737

QQl

-CH ₃

C ₂ H ₅ O

Le A23 COPY

Table 2 (continued) Example No. Het R ³

Ί "Λ 1 Q 1 C 7

V ^{IOIO /}

11-738

C ₂ H ₅ O

-CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

11-739

F ₃ C

-CH ₃

F F- j-0

11-743

-CH ₃

11-744

" ^CH 3

-CCH ₂ ) ₃ CH3

11-745 O ^ S / O ₂

11-746

J O ₂ N

- (CH ₂ ) ₃ CH ₃

-C ₂ H ₅ -CH ₂ -

Le A 23 EPO COPY

Table 2 (continued) Example No. Het R ³

11-747

'Us

cox; y

11-748

O ₂ N

CH ₂ CH ₂ OCH ₃ -CH ₂ CH ₂ OCH ₃

-CH ₂ CH ₂ OCH ₃

"-7 * 9 [QfV

11-750

CL

11-751

-CH ₃

-CH ₃ -CH ₃

-N

11-752

CL

-C ₂ H ₅

^π " ⁷⁵⁴

' ^CH 2 -CH = CH _{2 -CH 2} -CH = CH ₂

<3

.CH ₃

11-755

CL

Le A 23 EPO COPY β

The herbicidally active HeteroaryLoxyacetami de of the formula (II) are known see e.g. DE-OSn 28 22 155, 29 03 96: 6, 29 14 003, 30 18 075, 30 38 652, 30 38 599, 30 38 608, 30 38 635, 32 18 482 or EP-OSn 5501, 18 497, 29 171, 29 183, 60 426 or 94 541) or the subject of previous ones Patent applications (see e.g. DE-P 32 28 131 of July 28, 1982; DE-P 32 28 147 of July 28, 1982; DE-P 33 23 334 of June 29, 1983 and DE-P 34 00 168 of 4.1.1984 CLeA 22 7813).

They are obtained, for example, when using chloro-heteroaromatic compounds of formula (V),

Het - Cl (V)

in soft

Het has the meaning given above, with GlykoLsäureamiden of the formula (VI),

15 HO - CH ₂ - CO - N (VI)

\ _R 4

in which

R ³ and R ^{4 have} the meaning given above,

optionally in the presence of an acid binder, such as potassium carbonate or potassium hydroxide, and optionally in the presence of a diluent, such as methylene chloride or acetonitrile, at temperatures between 0 ° and +120 ⁰ C.

Le A 23 009

EPO COPY

The amides which can be used according to the invention as antidotes of formula (I) are particularly suitable for improving the tolerance of herbicidally active heteroaryloxyacetamides of formula (II) for important crops such as corn, soybeans, cotton, sugar beets, cereals, rice and sugar cane.

The active ingredient combinations according to the invention show a very good effect against weeds and grass weeds in numerous crops of useful plants. You can therefore go to selective Weed control in numerous crops be used. Weeds in the broadest sense are to be understood as meaning all plants that grow in places where they are undesirable.

The active ingredient combinations according to the invention can, for example can be used on the following plants:

Dicot weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Le A 23 009

copy m

-JUM-

Monocot weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus / Sorghum, Agropyron, Cynodon, Monochoria / Fimbristylis, Sagittaria, Eleusocharis, Scumir , Sphenoclea, Dactyloctenium, AgrostiS / Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum ,. Pineapple, asparagus, allium.

The use of the active ingredient combinations according to the invention however, it is by no means restricted to this genus, but extends in the same way to others Plants.

The active ingredient combinations according to the invention are particularly suitable for selective weed control in maize, soybeans, cotton, sugar beet, grain, rice and Sugar cane.

The selective herbicidal effectiveness of the invention Active ingredient combinations is particularly pronounced when herbicidal active ingredient and antidote are present in certain proportions. However, the weight ratios from herbicidal active ingredient to antidote in the inventive Combinations of active ingredients in relatively large areas vary. In general, there are from 0.01 to 100 parts by weight, preferably 0.1 to 20 parts by weight, of an antidote to 1 part by weight of herbicidal active ingredient of the formula (.II) of formula (I).

Le A 23 00 9

EPO COPY 0M

The countermeasures of the formula (I) which can be used according to the invention or the active ingredient combinations according to the invention from one GegenmitteL of the formula (I) and a herbicidal active ingredient of the formula (II) can be in the customary formulations such as solutions, emulsions, wettable powders, Suspensions, powders, dusts, pastes, soluble Powder, granules, suspension emulsion concentration, Active ingredient-impregnated natural and synthetic fabrics like finest encapsulation in polymeric materials.

These formulations "are prepared in a known manner, e.g. by mixing the active ingredients with extenders, that is, liquid solvents and / or solid carriers, optionally using surface-active substances Agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, organic solvents, for example, can also be used as auxiliary solvents be used. The following liquid solvents are essentially: aromatics, such as xylene, Toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, E.g. petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

Le A 23 009

EPO COPY

The following can be used as solid carriers:
z. B. ammonium salts and natural rock flour, such as
Kaolins, clays, talc, chalk, quartz, attapulgite,
Montmorillonite or diatomaceous earth and synthetic rock flour, such as highly dispersed silica, aluminum oxide and silicates, can be used as solid carriers for granulates: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granulates made from inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn on the cob and tobacco stalks; as emulsifying and / or foam-producing agents are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol

Ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates,
Alkyl sulfates, aryl sulfonates and protein hydrolysates;
Possible dispersants are: for example lignin sulphite waste liquors and methyl cellulose.

Adhesives such as carboxy-2Q methylcellulose, natural and synthetic powdery,
Granular or latex-shaped polymers can be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as
natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Further additives can be mineral and vegetable oils.

It can dyes such as inorganic pigments, for example
Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

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EPO COPY yy

The formulations generally contain between 0.1 and 95 percent by weight of a usable according to the invention Antidote or an active ingredient according to the invention combination of antidote and herbicidal active ingredient, they preferably contain between 0.5 and 90 percent by weight .

The antidotes that can be used according to the invention or those according to the invention Combinations of active ingredients can be used as such or in their formulations as a mixture with known ones Herbicides for weed control are used, finished formulation or tank mixing being possible. Also one Mixed with other known active ingredients, such as fungicides, Insectiζides, 'acaricides, nematicides, protective substances against Bird food, growth substances, plant nutrients and soil

15 structure improvement funds are possible:

The antidotes that can be used according to the invention or those according to the invention Combinations of active ingredients can be used as such, in the form of their formulations or those resulting from further Diluting prepared application forms, such as ready-to-use solutions, suspensions, emulsions, powders and Granules are applied. It is used in the usual way, e.g. by watering, squirting, atomizing, Dusting, scattering, dry pickling, wet pickling, wet pickling, Slurry pickling or encrusting.

The antidotes which can be used according to the invention can according to the methods customary for such antidotes are applied. So the inventively usable counter-

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EPOCOPY §

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applied before or after the herbicide or applied together with the herbicide. Furthermore, crop plants can be treated by seed treatment with the antidote before sowing (dressing) from harm be protected if the herbicide before or after Seed is applied. Another possible use consists in having the antidote when sowing in the seed furrow. If the plants are cuttings, you can do so before transplanting them treated with the antidote.

The application rate in the antidote is in principle independent the herbicide and the amount of herbicidal active ingredient applied. In general, the application rates of the antidote are included Surface treatment between 0.2 and 20 kg / ha, preferably between 0.5 and 5 kg / ha. When treating seeds are the application rates of antidotes in general between 0.2 and 200g per kilogram of seed, preferably between 0.5 and 50g per kilogram of seed. The application rates of active ingredient combinations according to the invention can be varied within a certain range. In general they are between 0.01 and 25 kg / ha, preferably between 0.05 and 15 kg / ha.

The application rates. herbicidal active ingredient vary in generally between 0.01 and 20 kg / ha, preferably between 0.05 and 10 kg / ha.

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B ³ O COPY

Example A.
Pre-emergence test procedure_2

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol

ether

To produce a suitable preparation of active ingredient, 1 part by weight of herbicidally active ingredient or antidote or a mixture of herbicidally active ingredient is mixed
and antidote with the specified amount of solvent,
add the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Procedure_2

An amount of antidote corresponding to 0.2% or another proportion of the seed weight is added with the same Weight of dextrin and 2 ml of methanol per 100 g of seeds (maize) for a few seconds together with the seeds in disposable cups shaken. The methyl alcohol then dries in a few

20 gen minutes at room temperature.

BAD ORlGlNAL

Le A 23 009

Untreated or stained with antidote according to procedure 2 Seeds of the test plants are sown in normal soil and after 24 hours with a herbicide preparation (method 1 and 2) or with the antidote preparation (method 1) or with the preparation of antidote and herbicidal Active substance (procedure 1 and 2) watered. The amount of water per unit area is expediently kept constant.

After three weeks, the inhibition of plant growth is rated in% in comparison with the untreated control. It means:

0% = no effect (like untreated control) 100% = total inhibition of the development of aboveground Plant parts

Active ingredients, application rates and results are shown in Tables 1 to 5.

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TABLE: 1 test on maize.

Herbi zi d: {ξ H)

_> 0CH ₂ -C0-N (11-643)

Antidote application according to procedure 1)

Antidote / CH ₃ (1-400) CL ₂ CH-CO-N CH ₂ -CH = N-OCH ₃ ^CH 2 "Tj N Application rate kg / ha X H inhibition H + A (ξ Α) CL ₂ CH-CO-N N-CO-CHCL ₂ CH ₂ -CH = CH ₂ H A. A. CL. CL (1-273) (1-280) ^CH3 I / ~~ \ I CH ₃ ^ H ₂ -CH = CH ₂ 20th
20th 0
0 CH-CO-N N-CO-CH
IUI
CH ₃ > ^ CH ₃ Cl ₂ CH-CO-N 7th
7th 1
3 80 0
0 0 (1-474) 8th 1 80 0 0 8th 3 0 20th 0 7th 1 20th 0 0 7th 3 80 0 0 8th 1 80 0 0 8th 3 0 20th
20th 0
0 7th
7th 1
3 0
0 80 10 8th 1 80 0 10 8th 3 0 20th 0 7th 1 - 20th 0 0 7th 3 80 0 0 8th 1 80 0 0 8th 3 0

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Tabel:

Testing on sharks

Herbicide:
(= H)

0-CH ₂ -CO-N (11-141)

Antidote application according to procedure 1

Antidote ... Application rate A. kg / ha % Inhibition H + A (= A) H 1
3 A. 0
0 CL Cl
i / \ ι
CH-CO-N N-CO-CH 0.75
0.75 0
0 CH ₃ ^^ CH ₃
(1-475) 1
3 0
0 CI ₂ CH-CO-NN-CO-CHC L ₂ 0.75
0.75 0
0 ^CH3 (I-400) 1
3 0
0 / H ₂ -CH = CH ₂
CL ₂ CH-CO-N 0.75
0.75 0
0 CH ₂ -CH = STILL ₃ (1-273) 1
3 0
0 JCH ₂ -CH = CH ₂
Cl ₂ CH-CO-N 0.75
0.75 0
0 (1-280) ^ ³ H 30th
30th 30th
30th 30th
30th "30
30th

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Table: 3 tests on sharks

Cl herbicide:

Cl

(11-40) Antidote application according to procedure 1

Antidote Application rate kg / ha % inhibition H + A (Ξ A) H _ A A. 30th
10 CL CL
CH -CO-N N-CO-CH
¹ <J ι
/ • II ^ S ^ "^ C \ 4
CI- 475) 0.25 1
0.25 3 0
10 H 70
70

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1SH

TABLE: 4
Testing on corn
Herbicide: ΓΛΛ

0-CH ₂ -CO-N

.CH ₃

^ C ₆ H ₅ ;

Seed dressing with 0.2% antidote according to method 2

Antidote
(= A)

Application rate kg / ha
H

% Inhibition A H + A

CL CL

I / ~ \ I

ch-co-n n-co-ch
1 Cj ι

CH ₃ ^ ~ ^ CH ₃

7 8

(1-475)

-CH ₃

CL ₂ CH-CO-N N-CO-CHCL ₂

7 8

CH ₃
(1-400)

^ CH ₂ -CH = CH ₂ CL ₂ CH-CO-N _1x

CH ₂ -CH = N-OCH ₃

(1-273)

CL ₂ CH-CO-N

, CH ₂ -CH = CH ₂

CH ₂ -

(1-280)

II.

7 8

20 80

20 80

20 80

20 80

0 0

0 0

0 20

0 0

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-IK-

Table: 5 Testing on maize herbicide: N — N

M Il

CH ₃

(Ξ H) F ₃ C- ¹ --S ^ --0-CH ₂ -CO-N ''

(11-141)

Seed dressing with 0.2% antidote according to method 2

Antidote Application rate ; kg / ha % inhibition H + A (Ξ A) H H A. 0 Cl Cl
ι J— \ '
CH-CO-N N-CO-CH
ι! ' 1 0.75 30th 0 CH ₃ ^^ CH ₃ (1-475) '0 CL ₂ CH-CO-N N-CO-CHCL ₂ 0.75 30th 0 CH ₃ ^ (1-400) 0 / CH ₂ -CH = CH ₂
CL ₂ CH-CO-N
^N CH ₂ -CH = N-OCH ₃ 0.75 30th 0 (1-273); 0 ^ CH ₂ -CH = CH ₂
Cl ₂ CH-CO-N 0.75 30th 0 CH ₂ ^
^c > N
M JJ (1-280)

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Claims (6)

3A18167 {claims 1. Use of amides of the formula (I) Il S ^R RCN (I) in which R stands for hydrogen, halogen or for each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, Bi eyeloaIky I, BicycloaIkeny I, Tricycloalkyl, aryl, heteroaryl, alkoxy, alkenyloxy, Alkinyloxy, aryloxy, carbamoyl, alkoxycarbonyl or dithiolanyl and R ¹ and R ² independently of one another each represent hydrogen, for formyl, for chlorosulfonyI or for each optionally substituted alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, cycloa tkeny I, Aj.koxy, AI ky 11hio, ^> alkylcarbonyI, alkoxycarbonyl, phenyl, phenoxy, phenylsulfonyl or heterocycyl, furthermore for amino, for alkylidenimino or for optionally substituted alkylcarbonylamino or di (alkylcarbonyl) amino, or R ¹ and R ² together with the nitrogen atom on which they are bound, for each optionally substituted alkylidenimino, pyrrolidinyl, piperidinyL, Piperidonyl, perhydroazepinyl, perhydroazocinyl, Dihydropyrazolyl, dihydro- or tetrahydropyridinyl, AzabicyclononyI, morpholinyl, perhydro-1,3-oxazinyI, 1,3-oxazolidinyI, 1,4-piperazinyI, perhydro-1,4-diazepinyl, dihydro-, tetrahydro- or perhydroquinolyl- or isochino IyI, indolyl, dihydro- or perhydroi ndoIyI. Le A 23 009 EPO COPY as an antidote to improve crop tolerance of herbicidally active heteroaryloxyacetamides of the formula (II), Het - O - CH ₂ - CO - N (II) 5 in which Het for an optionally substituted 5-membered Heterocycle, which can also be linked to benzoanne and R ³ and R ⁴ independently represent hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkoxyalkoxy, heterocyclyl or optionally substituted aryl or R ³ and R ⁴ together with the nitrogen atom to which they are attached represent an optionally substituted, saturated or unsaturated heterocycle which can contain further heteroatoms. 2. Process for improving crop plant tolerance of herbicidally active heteroaryloxyacetamides of the formula (II) according to claim 1, characterized / that amides of the formula (I) according to claim 1 together with the heteroaryloxyacetamides (II) can act on the cultivated plants and / or their habitat. ίθ Α 23 009 'EPO COPY 3. means for selective weed control in crops of useful plants, characterized by a content of an active ingredient combination consisting of an amide of the formula (I) according to Claim 1 and - At least one herbicidal heteroaryloxyacetamide of the formula (II) according to Claim 1. 4. Methods for selective weed control in crops of useful plants, characterized in that an active ingredient combination according to claim 3 on the 10 weeds or their habitat can act. 5. Use of an active ingredient combination according to claim 3 for selective weed control in crops of useful plants. 6. Process for the preparation of means for selective weed control in crops of useful plants, thereby characterized in that active ingredient combinations according to claim 3 with extenders and / or surfactants mixed. Le A 23 009 EPO COPY A