Aromatic amides, their preparation process and their use as...

Details Aromatic amides, their preparation process and their use as... Aromatic amides, their preparation process and their use as...

1999-10-07

2003-04-29

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C514S617000, C564S134000, C564S139000, C564S140000

Reexamination Certificate

active

06555709

ABSTRACT:

This application is a 371 of PCT/EP98/02014, filed Apr. 7, 1998.
The present invention relates to aromatic amides, their preparation process and their use as pesticides.
A subject of the invention is the compounds of formula (I):
in which:
a, b, c and d, identical to or different from one another, represent a hydrogen atom, a halogen atom, an alkyl, alkenyl or alkynyl, O-alkyl, O-alkenyl or O-alkynyl, S-alkyl, S-alkenyl or S-alkynyl radical containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, a C≡N, NO
2
or NH
2
radical, the substituents a, b, c and d being able to form between themselves rings, preferably one, which either contain or do not contain one or more, preferably one or two, hetero atoms, preferably from the group consisting of S, O and N, and which are substituted, or unsubstituted.
Y and W, identical to or different from one another,
represent both a
 radical or both a
 radical in which e, f and e′, identical or different, represent a hydrogen atom, a halogen atom, a free, etherified or esterified hydroxyl radical, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms;
X represents a
 radical or a
 radical in which g, h and g′, identical or different, represent a hydrogen atom, a halogen atom, a free, etherified or esterified hydroxyl radical, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or X represents a C═O radical, an oxygen atom or a nitrogen atom, or X forms with the carbon in position 2 belonging to radical q an epoxy bridge, a cyclic hydrocarbonated radical optionally substituted by one or more halogen atoms;
q represents a C═ radical or a CD radical, in which D represents a hydrogen atom, a halogen atom or an alkyl or alkoxy radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or D forms with the carbon atom which carries it and one of the carbon atoms adjacent to it a carbon-carbon double bond, an epoxy radical, a cyclic hydrocarbonated radical, optionally substituted by one or more halogen atoms;
n represents an integer varying from 0 to 8;
Z represents a
 radical in which I and k, identical or different, represent a hydrogen atom, a halogen atom, a C≡N radical, a free, etherified or esterified hydroxyl radical, an SR′ radical, wherein R′ is an organic rest containing up to 8 carbon atoms, preferably S-alkyl, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or Z represents an oxygen, sulfur, nitrogen atom, a C═O or C═S radical, it being understood that if n is greater than 1, Z can take different values,
R represents an oxygen or sulfur atom;
R
1
and R
2
, identical to or different from one another, represent a hydrogen atom, a linear, branched or cyclic, saturated or unsaturated, optionally substituted alkyl, CO-alkyl, CONH-alkyl or CO
2
alkyl radical contaning up to 8 carbon atoms, optionally interrupted by one or more preferably non-adjacent heteroatoms, preferably from the group consisting of N, O, S, or an optionally substituted aryl or heteroaryl radical,
the —C—(Z)
n
chain is fixed in position 3 or 4 of the benzamide, the dotted lines representing one or more optional double bonds,
in all their possible isomeric forms as well as their mixtures.
By compound of formula (I) are designated all the geometric isomers and stereo-isomers taken individually or in a mixture.
In the definition of substituents:
alkyl preferably represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
n-pentyl, isopentyl, cyclopropyl, cyclobutyl or cyclopentyl radical,
alkenyl preferably represents a vinyl, 1-propenyl, 2-methyl 2-propenyl or isopropenyl radical,
alkynyl preferably represents an ethynyl, 1-propynyl, 2-propynyl or pent-2-ene-4-enyl radical,
halogen preferably represents a fluorine, chlorine, bromine or iodine atom,
aryl preferably represents a carbocyclic aromatic group containing 4 to 10 carbon atoms, particularly preferably a phenyl, naphthyl, dihydronaphthyl, tetrahydronaphthyl, indanyl or indenyl radical,
a heterocyclic radical is preferably a heteroaryl radical or a saturated or unsaturated 3 to 8 membered ring comprising one, two three or four heteroatoms from the group consisting of N, O and S.
heteroaryl is preferably a 3 to 7 membered aromatic ring comprising one, two, three or four heteroatoms from the group consisting of N, O and S, particularly preferred thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isothiazolyl, isoxazolyl, oxazolyl, thiazolyl, oxadiazolyl and tetrazinyl
Particularly preferred heterocyclic radicals are a thienyl, furyl, pyrannyl, pyrrolyl, 2H-pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isothiazolyl, isoxazolyl, furazanyl, thiazolyl, oxazolyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolinyl, piperidyl, piperazinyl, morpholinyl, izapinyl, thiazinyl, tetrazinyl, oxathiolanyl or thiadiazinyl radical.
When the aryl or heterocyclic radical is substituted, it is preferably substituted by one or more substitutents chosen in particular from halogen atoms, alkyl or alkoxy radicals containing up to 8 carbon atoms, or methylenedioxy, difluoromethylenedioxy, tetrafluoro ethylenedioxy, cyano, nitro, cyanato, thiocyanato, pentafluorothio or fluorosulfonyl groups.
Etherified or esterified preferably means etherified with a linear or branched C
1
-C
8
-alkyl group or esterified with a (C
1
-C
8
)-carboxylic acid.
If any of the substituents a-d form a ring it is preferably a 4 to 8 membered ring which is preferably monounsaturated (due to fusion with the naphthyl group) and is carbocyclic or contains preferably one or two heteroatoms from the group consisting of N, O and S.
If Z is O, N, or CO, CS and n is greater then 1 it is preferred that heteroatoms are not adjacent to each other and CO, CS are not adjacent to each other.
It goes without saying that x, q and Z have to be chosen in a way that a tetravalent carbon at q results.
Particularly preferred are compounds of formula (I) in which Y represents a —CH
2
— radical, those in which Y and W represent a CH radical and together form a double bond in position 3(4), those in which W represents a CH
2
radical, those in which q and X represent a CH═ radical and together form a double bond, those in which q represents a CH or C═ radical, those in which X represents a CH, a CH
2
, a CHOH or a CO radical, those in which Z represents a CH
2
a CHF, a CHOH or a COOCH
3
radical, those in which n represents the number 1, those in which R represents an oxygen atom, those in which R
1
represents a hydrogen atom, those in which R
2
represents an alkyl radical containing up to 8 carbon atoms or a phenyl radical optionally substituted by one or more halogen atoms and/or one or more linear or branched alkyl radicals containing up to 8 carbon atoms in particular in which R
2
represents an alkyl radical containing up to 6 carbon atoms and in particular an isobutyl radical or a 2-methylphenyl radical, those in which at least one of substituents a, b, c and d represents a halogen atom, (C
1
-C
8
) alkyl or (C
1
-C
8
) alkoxy for example those in which two of the substituents a, b, c and d represent a chlorine or bromine atom, the compounds of formula (I) in which two of the substituents a, b, c and d represent a hydrogen atom.
In particular a subject of the invention is the compounds the preparation of which is given hereafter in the experimental part and quite particularly the compounds of Examples A, B, C, D, E, F, G, H, I, J, K, L and M.
The compounds of formula (I) can be used to combat harmful organisms such as arthropods, for example insects and acaridae, and helminths, for example nematodes, or molluscs, for example slugs. Therefore a subject of the present invention is a process for combating arthropods and/or helminths and/or molluscs, which comprises the administration to the

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