N-acylimino heterocyclic compounds

Patent metadata

Field	Value
Publication number	US-9783523-B2
Application number	US-201415038272-A
Country	US
Kind code	B2
Filing date	Nov 21, 2014
Priority date	Nov 22, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The present invention relates to N-acylimino compound of formula (I):

wherein X is O or S, in particular O;
Y is a single bond, O, S or NR 5 ; Het is a 5 or 6 membered carbon-bound or nitrogen-bound heterocyclic ring, W 1 -W 2 -W 3 -W 4 represents a carbon chain group connected to N and C═N, and thus forming a saturated, unsaturated, or partially unsaturated 5 or 6 membered nitrogen containing heterocycle, wherein W 1 , W 2 , W 3 and W 4 each individually represent CR v R w ; R 1 , R 2 may be hydrogen, halogen, etc.; R 3 may be hydrogen, CN, C 1 -C 6 -alkyl, etc.; R 4 may be of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 3 -C 8 -cycloalkyl, Q-phenyl, Q′-O-phenyl, Q′-S-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1, 2, 3, 4 or 5 identical or different substituents R 10 , and the moieties Q-Het # , Q′-O-Het # and Q′-S-Het # where Het# represents a heterocyclic radical and where Q and Q′ are C 1 -C 6 -alkandiyl, C 2 -C 6 -alkendiyl, or C 2 -C 6 -alkyndiyl, and where Q may also be a single bond; R 3 and R 4 together may also may also a bivalent radical, selected from the group consisting of C 2 -C 5 -alkandiyl, C 2 -C 5 -alkendiyl, Q″-C 1 -C 4 -alkandiyl and Q″-C 2 -C 4 -alkendiyl, where Q″ is O or S.

The invention also relates to the use of the N-acylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein
X is O or S;
Y indicates a single bond between N and R 4 or Y is O, S, S(═O), S(═O) 2 , CHR 5a or N—R 5 ;
Het is a 5 or 6 membered carbon-bound or nitrogen-bound heterocyclic or heteroaromatic ring, comprising 2, 3, 4 or 5 carbon atoms and 1, 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen or nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R 6 , wherein k is an integer selected from 0, 1, 2, 3 and 4;
W 1 -W 2 -W 3 -W 4 represents a carbon chain group connected to N and C═N, and thus forming a saturated, unsaturated, or partially unsaturated 5 or 6 membered nitrogen containing heterocycle, wherein
W 1 , W 2 , W 3 and W 4 each individually represent CR v R w , wherein
each R w independently from each other, is selected from the group consisting hydrogen, halogen, cyano, azido, nitro, SCN, SF 5 , C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, and wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated and/or may optionally be substituted with 1, 2 or 3 identical or different radicals R 7 ,
OR 8 , NR 9a R 9b , S(O) n R 8 , S(O) n NR 9a R 9b , C(═O)R 7a , C(═O)NR 9a R 9b , C(═O)OR 8 , C(═S)R 7a , C(═S)NR 9a R 9b , C(═S)OR 8 , C(═S)SR 8 , C(═NR 17 )R 7a , C(═NR 17 )NR 9a R 9b and Si(R 11 ) 2 R 12 ,

each R v independently from each other, are selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or may be partly or fully halogenated or may optionally be further substituted with 1, 2 or 3 identical or different radicals R 7 ; or
R v and R w present in one of the groups may together form ═O, ═CR 13 R 14 , ═S, ═NR 17 , —NOR 16 , —NNR 9a R 9b ,
or
two R w of adjacent carbon atoms, may form both together and together with the existing bond a double bond between the adjacent carbon atoms;

and wherein one of W 2 or W 3 may optionally represent a single or a double bond between the adjacent carbon atoms;

R 1 , R 2 are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1, 2 or 3 radicals R 7 ,
Si(R 11 ) 2 R 12 , OR 8 , OSO 2 R 8 , S(O) n R 8 , S(O) n NR 9a R 9b , NR 9a R 9b , C(═O)NR 9a R 9b , C(═S)NR 9a R 9b , C(═O)OR 8 , C(═O)R 7a , C(═S)R 7a , phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R 10 ,
a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1, 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R 7 ,
or
R 1 and R 2 may together be ═O, ═CR 13 R 14 , ═S, ═NR 17 , ═NOR 16 or ═NNR 9a R 9b ;

R 3 is selected from the group consisting of hydrogen, halogen, NO 2 , CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkoxy, wherein each of the 9 last mentioned radicals are unsubstituted, partly or completely halogenated and/or carry 1, 2, 3 or 4 radicals R 7d , it being also possible for cycloalkyl to carry 1, 2, 3, 4, 5 or 6 C 1 -C 4 -alkyl groups, which are unsubstituted or partly or completely halogenated,
OR 8 , NR 9a R 9b , C(═O)OR 8 , C(═O)NR 9a R 9b , C(═NR 21 )OR 8 , C(═NOR 21 )OR 8 , C(═NR 21 )NR 9a R 9b , C(═NOR 21 )NR 9a R 9b , C(═S)NR 9a R 9b , C(═O)R 7a , C(═S)R 7a , C(═NR 21 )R 7a , C(═N—Y—R 22 )R 7a , S(O) n R 8 , S(O) n NR 9a R 9b , S(═O)(═NR 16a )R 8 ,
phenyl, benzyl, phenethyl, phenylethenyl, phenylethynyl, where the phenyl ring in the last five mentioned radicals is unsubstituted or may be substituted with 1, 2, 3, 4 or 5 identical or different substituents R 10 ,
and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1, 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

R 4 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 3 -C 8 -cycloalkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated or carry 1 or 2 radicals R 7 , it being also possible for cycloalkyl radicals to carry 1, 2, 3, 4, 5 or 6 C 1 -C 4 -alkyl groups,
the moieties Q-phenyl, Q′-O-phenyl and Q′-S-phenyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R 10 ,
and the moieties Q-Het # , Q′-O-Het # and Q′-S-Het # where
Het # represents a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the heterocyclic ring is optionally substituted with 1, 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, and
Q irrespectively of its occurrence, is a single bond, C 1 -C 6 -alkandiyl, C 2 -C 6 -alkendiyl, or C 2 -C 6 -alkyndiyl,
Q′ irrespectively of its occurrence, is C 1 -C 6 -alkandiyl, C 2 -C 6 -alkendiyl, or C 2 -C 6 -alkyndiyl,

or if Y is NR 5 , the radical R 4 may also be C(═O)OR 18 , C(═O)NR 19a R 19b , C(═S)NR 19a R 19b , C(═O)R 20 or C(═S)R 20 , or
R 3 and R 4 together may also a bivalent radical, selected from the group consisting of C 2 -C 5 -alkandiyl, C 2 -C 5 -alkendiyl, Q″-C 1 -C 4 -alkandiyl and Q″-C 2 -C 4 -alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1, 2, 3 or 4 radicals R 7c , and wherein Q″ is selected from O and S(═O) n and bound to the carbon atom, which carries R 3 and wherein one CH 2 group in C 2 -C 5 -alkandiyl and C 2 -C 5 -alkendiyl, which is not adjacent to Y, may be replaced by O or S(═O) n ;
R 5 is selected from the group consisting of hydrogen, halogen, CN, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated,
phenyl, phenyl-C 1 -C 4 -alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1, 2, 3, 4

Assignees

• Basf Se

Inventors

• Bandur Nina Gertrud
• Dietz Jochen
• Pohlman Matthias
• Mclaughlin Martin John
• Gockel Birgit
• Körber Karsten
• Von Deyn Wolfgang

Classifications

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D401/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title