Patent ID: 6107299
Filing Date: 2000-08-22
Classification: A01N,C07D,C07F

Abstract:
A compound of formula I, N-oxides or salts ##STR118## in which q is 0, 1 or 2R.sup.1 is hydrogen, halogen, (C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.8)-haloalkyl, (C.sub.1 -C.sub.8)-alkoxy or (C.sub.3 -C.sub.6)-cycloalkyl;R.sup.2 and R.sup.3 are identical or different and are each hydrogen, (C.sub.1 -C.sub.8)-alkyl, (C.sub.2 -C.sub.8)-alkenyl, (C.sub.2 -C.sub.8)-alkynyl, (C.sub.1 -C.sub.8)-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C.sub.1 -C.sub.8)-alkoxycarbonyl, (C.sub.1 -C.sub.8)-alkylthio, (C.sub.1 -C.sub.8)-alkylsulfinyl, (C.sub.1 -C.sub.8)-alkylsulfonyl, amino, (C.sub.1 -C.sub.8)-alkylamino, (C.sub.1 -C.sub.8)-dialkylamino or (C.sub.3 -C.sub.6)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkynyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, groups, a saturated carbon unit can be replaced by oxygen, S(O).sub.x, where x=0, 1 or 2 or by dimethylsilyl and further in these groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; orR.sup.2 and R.sup.3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH.sub.2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, halogen, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-haloalkoxy; orR.sup.2 and R.sup.3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH.sub.2 groups and which may be substituted by 1, 2 or 3 (C.sub.1 -C.sub.4)-alkyl groups;A is CH and D is N.sup.+ R.times.1/n Q.sup.n- orA is N and D is N.sup.+ R.times.1/n Q.sup.n- orA is CH or N and D is N orA is N.sup.+ R.times.1/n Q.sup.n- and D is N,R is CR.sup.6 R.sup.7 D.sup.a R.sup.8,Q.sup.n- is an inorganic or organic anion, n being 1, 2, 3 or 4;X is NH, O or S(O).sub.q, (q is 0, 1 or 2);R.sup.4 and R.sup.4', which may be the same or different, are hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-halogenalkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkylthio;R.sup.5 is the group ##STR119## l is 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4, each R.sup.9, which may be the same or different from any other R.sup.9, is (C.sub.2 -C.sub.8)-haloalkenyloxy, (C.sub.2 -C.sub.8)-haloalkynyl, (C.sub.2 -C.sub.8)-haloalkynyloxy, (C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-haloalkoxy, oxiran-2-ylmethoxy, oxetan-2-ylmethoxy, isopropylidenoamino-oxy, isopropylidenamino-oxy-(C.sub.1 -C.sub.4)-alkoxy, formyl, --SF.sub.5, hydroxy or heterocyclyloxy, in which the last named group may be substituted by up to three of the same or different D.sup.1 R.sup.12, cyano, nitro or halogen, orR.sup.9 is a group Z--R.sup.11, in whichZ is OSO.sub.2, NR.sup.13 SO.sub.2, UC(.dbd.W)V, U.sup.1 P(W.sup.1)(V.sup.1 R.sup.11)V.sup.2, SO.sub.2 NR.sup.13, SO.sub.2 O, NR.sup.13 SO.sub.2 NR.sup.13, OSO.sub.2 NR.sup.13, NR.sup.13 SO.sub.2 O, Si(OR).sup.13 R.sup.13, N(O)R.sup.13, NR.sup.13 O, NR.sup.13 NR.sup.13, N.dbd.N, N.dbd., NR.sup.13 --N.dbd., D.sup.1-- N.dbd. andU.sup.1 is a direct bond, oxygen, NR.sup.13 or sulfur,U is oxygen, NR.sup.13 or sulfur, or when W or V is NR.sup.13 or sulfur, it can also be a direct bond,W is oxygen, NR.sup.130 or sulfur, andR.sup.130 is hydrogen, nitro, cyano, optionally substituted alkyl, optionally substituted acyloxy, optionally substituted aryl, optionally substituted heteroaryl, hydroxy, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, mono- or disubstituted amino;W.sup.1 is oxygen or sulfur,V, V.sup.1, V.sup.2, independently of each other are a direct bond, NR.sup.13, oxygen or sulfur,each R.sup.13, which may be the same or different from any other R.sup.13, is hydroxy, alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyl or optionally substituted acyloxy,R.sup.11 is (C.sub.1 -C.sub.20)-alkyl, (C.sub.2 -C.sub.20)-alkenyl, (C.sub.2 -C.sub.20)-alkynyl, (C.sub.3 -C.sub.8)-cycloalkyl or (C.sub.4 -C.sub.8)-cycloalkenyl, in which groups optionally one or more, generally up to three, CH.sub.2 -groups can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO.sub.2, NR.sup.13 or SiR.sup.16 R.sup.17, and these groups may be substituted by up to three of the same or different D.sup.2 R.sup.14, cyano, nitro or halogen, orR.sup.11 is hydrogen, aryl or heterocyclyl, in which the last named group may be substituted by up to three of the same or different D.sup.3 R.sup.15, cyano, nitro or halogen, or when V is NR.sup.13, R.sup.13 and R.sup.11 can together form a 4- to 8-membered ring, in which one or two CH.sub.2 -groups, is replaced by oxygen; S(O).sub.t, where t=0, 1 or 2, or NR.sup.19, in whichD.sup.1, D.sup.2 and D.sup.3, independently of each other, are a direct bond, oxygen, S(O).sub.k, SO.sub.2 O, OSO.sub.2, CO, OCO, COO, NR.sup.13', SO.sub.2 --NR.sup.13', NR.sup.13' SO.sub.2, ONR.sup.13', NR.sup.13' O, NR.sup.13' CO, CONR.sup.13' or SiR.sup.16 R.sup.17, and k=0, 1 or 2 and R.sup.13' has the same meaning as R.sup.13,R.sup.16, R.sup.17, independently of each other, are (C.sub.1 -C.sub.4)-alkyl;R.sup.12, R.sup.14 and R.sup.15 are hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.4 -C.sub.8 -cycloalkenyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, C.sub.4 -C.sub.8 -cycloalkenyl-C.sub.1 -C.sub.4 -alkyl, aryl, heterocyclyl, aryl-C.sub.1 -C.sub.4 -alkyl or heterocyclyl-C.sub.1 -C.sub.4 -alkyl, in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, CH.sub.2 -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more of the same or different groups selected from halogen, hydroxy and cyano and in the case of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more of the same or different substituents R.sup.18 ;R.sup.18 is (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, cyano, nitro or halogen;R.sup.19 is hydrogen, (C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.2 -C.sub.4)-haloalkanoyl, (C.sub.2 -C.sub.4)-alkoxyalkyl, phenyl-(C.sub.1 -C.sub.4)-alkyl or phenyl and the phenyl groups are unsubstituted or substituted by one or more of the same or different substituents R.sup.20,R.sup.20 is (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, halogen or cyano;R.sup.10 is cyano, nitro, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.4 -C.sub.8 -cycloalkenyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, C.sub.4 -C.sub.8 -cycloalkenyl-C.sub.1 -C.sub.4 -alkyl, aryl, heterocyclyl, aryl-C.sub.1 -C.sub.4 -alkyl or heterocyclyl-C.sub.1 -C.sub.4 -alkyl in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, CH.sub.2 -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more of the same or different groups selected from halogen, hydroxy and cyano and in the case of of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more of the same or different substituents R.sup.21,R.sup.21 has the same meaning as R.sup.18, ortwo adjacent R.sup.9 and/or R.sup.10 groups together with the carbon atoms two which they are attached can form an unsaturated 5- or 6-membered carbocyclic ring, which in a 5 membered ring, a CH.sub.2 can be replaced by an oxygen- or sulfur atom and in a 6 membered ring, one or two CH units can be replaced by one or two nitrogen atoms or substituted by 1, 2 or 3 of the same or different groups selected from (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, halogen, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-haloalkoxy; ortwo adjacent R.sup.9 and/or R.sup.10 groups together with the carbon atoms to which they are attached can form a saturated 5- or 6- or 7 membered carbocyclic ring, in which, one or two CH.sub.2 units can be replaced by one or two oxygen and/or sulfur and can be substituted by 1, 2 or 3 (C.sub.1 -C.sub.4)-alkyl groups, and further whenA is CH and D is N.sup.+ R.times.1/n Q.sup.n- orA is N and D is N.sup.+ R.times.1/n Q orA is N.sup.+ R.times.1/n Q.sup.n- and D is NR.sup.9 can also be (C.sub.2 -C.sub.6)-alkynyl, (C.sub.2 -C.sub.6)-alkynyloxy or (C.sub.2 -C.sub.6)-haloalkenyl;R.sup.6 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl or a negative charge, which can represent Q.sup.n-R.sup.7 is hydrogen, halogen, CN, nitro, (C.sub.1 -C.sub.4)-alkoxycarbonyl, (C.sub.1 -C.sub.4)-alkylcarbamoyl, di-(C.sub.1 -C.sub.4)-alkylcarbamoyl, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.1 -C.sub.8)-alkyl, (C.sub.2 -C.sub.8)-alkenyl, (C.sub.2 -C.sub.8)-alkynyl, aryl or (C.sub.3 -C.sub.8)-cycloalkyl.D.sup.a is a direct bond, NR.sup.70, N(O)R.sup.70, O, S, SO, SO.sub.2, C(.dbd.W.sup.a), OC(.dbd.W.sup.a), U.sup.a (C.dbd.W.sup.a)V.sup.a where U.sup.a and V.sup.a are a direct bond, NR.sup.70, S or O, except V.sup.a is not a bond when U.sup.a is bond or O; SiR.sup.72 R.sup.73, U.sup.b (P.dbd.W.sup.b)V.sup.b V.sup.c, U.sup.b (SO.sub.2)U.sup.c where one of U.sup.b and U.sup.c is a direct bond, NR.sup.70, S or O and the other is NR.sup.70 ; U.sup.a (CW.sup.a)(CW.sup.a)V.sup.b, NR.sup.70 O, O NR.sup.70, NR.sup.70 NR.sup.70, N.dbd.N, --N.dbd., --NR.sup.70 --N.dbd. or --O--N.dbd., and W.sup.a is O, S or NR.sup.71 ; W.sup.b is O or S;U.sup.a, V.sup.b and V.sup.c, independently of each other are a direct bond, NR.sup.70, S or O each R.sup.70, which may be the same or different from any other R.sup.70, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R.sup.6, R.sup.112 OR R.sup.113, respectively with the D.sup.a, D.sup.12 OR D.sup.13 to which they are attached; each R.sup.71, which may be the same or different from any other R.sup.71, is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy; R.sup.72 and R.sup.73 are alkyl or optionally substituted aryl; andR.sup.8 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH.sub.2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO.sub.2, NR.sup.70 or Si R.sup.72 R.sup.73 and can also be substituted by nitro, halogen, SF.sub.5 or D.sup.12 R.sup.112, and in the case D.sup.a is U.sup.b P(.dbd.W.sup.b)V.sup.b V.sup.c, the two R.sup.6 groups together with the V.sup.b PV.sup.c, to which they are attached can form a 4 to 8 membered ring,D.sup.12 is a direct bond, NR.sup.70, N(O)R.sup.70, O, S, SO, SiR.sup.72 R.sup.73, U'(CW')V', U.sup.1' (PW.sup.1')V.sup.1' V.sup.2', U.sup.2' (SO.sub.2)U.sup.3', Si(OR.sup.72)R.sup.73, Si(OR.sup.72)(OR.sup.73), NR.sup.70 O, ONR.sup.70, NR.sup.70 NR.sup.70, N.dbd.N, .dbd.N--, .dbd.N--NR70-- .dbd.N--O--, --N.dbd., --NR.sup.70 --N.dbd. or --O--N.dbd. andU', U.sup.1' V', V.sup.1' and V.sup.2', independently of each other are a direct bond, NR.sup.70, S or OW' is O, S or NR.sup.71 ;W.sup.1' is O or S;U.sup.2' and U.sup.3', independently of each other are a direct bond, NR.sup.70 or O;R.sup.112 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH.sub.2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO.sub.2, NR.sup.70 or SiR.sup.72 R.sup.73 and can also be substituted by nitro, halogen, SF.sub.5 or D.sup.13 R.sup.113 and in which two adjacent D.sup.12 R.sup.112 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C.sub.1 -C.sub.4 -alkyl; is a negative charge for D.sup.12 .dbd.(CO)O, (SO.sub.2)O, U.sup.1' (PW.sup.1')V.sup.1' O which replaces the ion Q.sup.n- ; orR.sup.112 is hydrogen when D.sup.12 is O(CO)NH, NR.sup.70 (CO)NH, O(CS)NH, NR.sup.70 (CS)NH, (CO)NH, (CS)NH, O(CO), NR.sup.70 (CO), SO2NH;D.sup.13 has the same meaning as D.sup.12 and R.sup.113 has the same meaning as R.sup.112.