O-benzyl oxime ether derivatives and their use as pesticides

Details O-benzyl oxime ether derivatives and their use as pesticides O-benzyl oxime ether derivatives and their use as pesticides

2000-09-27

2002-01-29

O'Sullivan, Peter (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C514S238200, C514S311000, C514S357000, C514S365000, C514S438000, C514S466000, C514S469000, C514S471000, C514S524000, C514S599000, C544S160000, C546S077000, C546S175000, C546S331000, C548S204000, C549S491000, C549S495000

Reexamination Certificate

active

06342633

ABSTRACT:

The present invention relates to compounds of the formula I
in which
Y is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, OH, CN, NO
2
, Si(CH
3
)
3
, CF
3
or halogen,
Z is a group a)
 and in which the remaining substituents are defined as follows:
R
1
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
-alkynyl, C
3
-C
6
cycloalkyl, phenyl which is unsubstituted or at most trisubstituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, or benzyl which is unsubstituted or at most trisubstituted in the aromatic ring in the same manner or is cyclopropylmethyl, C
1
-C
4
haloalkyl, C
2
-C
5
alkoxyalkyl, cyanomethyl CO—R
6
, OH, NH
2
, C
1
-C
4
alkylamine or C
1
-C
4
alkoxycarbonyl-C
1
-C
2
alkyl;
X is oxygen, sulfur or NR
5
;
R
2
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl, C(O)R
6
, OH C
1
-C
4
alkoxy, NH
2
or C
1
-C
4
alkylamine;
R
5
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkyny;
R
6
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxycarbonyl or phenyl which is unsubstituted or at most trisubstituted;
and in which R
3
and R
4
independently of one another are hydrogen, cyano, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl, cyclopropylmethyl, C
1
-C
4
alkoxy, C
2
-C
5
alkoxyalkyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkylthio, C
2
-C
5
alkylthioalkyl; a ring having not more than 15 ring carbon atoms which can be polymemberd, and is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S, it being possible for this ring to be bonded via an aliphatic bridge having not more than 4 carbon atoms and/or via either CO, oxygen or sulfur; or
in which R
3
and R
4
together with the shared carbon atom are a ring or a polymembered ring system having not more than 15 ring carbon atoms which is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S;
the possible substituents of all these rings mentioned for R
3
and R
4
, either individually or in combination, being selected from amongst C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
haloalkynyl, C
1
-C
4
haloalkoxy, halogen, cyano, cyano-C
1
-C
2
alkyl, cyano-C
1
-C
2
aloxy, OH, NO
2
, SCN, thiocyanomethyl, Si(CH
3
)
3
, NH
2
, NH(C
1
-C
4
alkyl), N(C
1
-C
4
alkyl)
2
, C
1
-C
4
alkoxymethyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkoximinomethyl, —CSNH
2
, —SH, C
1
-C
4
alkylthio, C
1
-C
4
alkylthiomethyl, C
2
-C
4
alkenyloxy, C
2
-C
4
alkynyloxy, C
2
-C
4
haloalkenyloxy, C
1
-C
4
alkylsulfinylmethyl, C
1
-C
4
alkylsulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C
3
-C
6
cycloalkyl; phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio; it being possible for the last-mentioned aromatic substituents to have not more than three further substituents in the phenyl ring which are selected from amongst halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy, CN and NO
2
and it being possible for two of the substituents, of which there are not more than 3, to form, together with the adjacent substituents, an aliphatic bridge which has not more than 5 members and which has 0-2 oxygen atoms and 0-1 carbonyl group and which can be not more than tetrasubstituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy and/or by a single phenyl group.
In a narrower sense of the meaning the invention refers also to the above-mentioned group of compounds of formula I, wherein R
1
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl; or is phenyl which is unsubstituted or at most trisubstituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio; or is benzyl which is unsubstituted or at most trisubstituted in the aromatic ring in the same manner, and wherein R
2
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alknyl, C
3
-C
6
cycloalkyl, C(O)R
6
, OH or C
1
-C
4
alkoxy.
If asymmetric carbon atoms are present in the compounds of the formula I, the compounds occur in optically active form. On account of the presence of the imino double bond on its own, the compounds in any case occur in the [E]- or [Z]-form. Atropisomerism can also occur. The formula I is intended to include all these possible isomeric formulae and also their mixtures, e.g. racemic mixtures and any desired [E/Z]-mixtures.
The compounds according to the invention have fungicidal properties and are suitable as fungicidal active ingredients in crop protection.
If the compounds I have at least one basic centre, they can form acid addition salts. These are formed, for example, with strong inorganic acids, such as mineral acids, for example sulfuric acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as C
1
-C
4
alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as C
1
-C
4
alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Due to the close relationship between the compounds I in free form and in the form of their salts, they are, analogously, to be understood as meaning, if appropriate, the relevant salts or the free compounds I.
Unless otherwise defined, the general terms used hereinabove and hereinafter are defined as follows.
Alkyl groups on their own or as structural element of other groups are straight-chain or branched, depending on the number of carbon atoms. C
1
-C
4
Alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl.
Alkenyl as a group or as structural element of other groups and compounds, such as alkenyloxy, arylalkenyl and heteroarylalkenyl, is either straight-chain, for example ethenyl, propen-1-yl or but-1-en-1-yl, or branched, for example propen-2-yl or but-1-en-2-yl.
Alkynyl as a group or as structural element of other groups and compounds, such as alkynyloxy, is either straight-chain, for example ethynyl, propyn-1-yl or but-1-yn-1-yl, or branched, for example propyn-2-yl or but-1-yn-2-yl.
Cycloalkyl as a group or as structural element of other groups and compounds, such as cycloalkylmethoxy, is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Carbocyclic rings on their own or as structural element of other groups, such as aryl-C
1
-C
4
alkyl, aryloxy-C
1
-C
4
alkyl, arylthio-C
1
-C
4
alkyl, arylcarbonyl and aryl-C
2
-C
4
alkenyl groups, have, in particular, 6 to 14 C atoms and are, for example, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl, phenanthryl or in particular phenyl. They can be aromatic, partially hydrogenated or completely saturated. One or two benzene rings may be fused to carbocyclic rings.
Rings having hetero atoms, as a group as such and as structural element of other groups and compounds, such as heteroaryl-C
1
-C
4
alkyl, heteroaryloxy-C
1
-C
4
alkyl, heteroarylthio-C
1
-C
4
alkyl, heteroarylcarbonyl and heteroaryl-C
2
-C
4
alkenyl groups, have, in particular, 5 to 14 ring members, of which 1 to 3 members are hetero atoms selected from amongst the group oxygen, sulfur and nitrogen. Examples which may be mentioned are benzimidazolyl, benzocumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, ethylenedioxyphenyl, furyl, imidazolyl, indazolyl, indolyl, isoquinolyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo&

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