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1. WO2012065905 - CYANOENAMINES AND THEIR USE AS FUNGICIDES

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

Patent Claims

Cyanoenamines derivatives of the formula (I)


in which

R represents one of the following groups R A or R1


n represents 1, 2, 3 or 4,

m represents 1, 2, 3 or 4,

t represents 0 or 1,

Yl represents S, O or NR5,

Y2 represents S, O or NR7,

Y3 represents a bond or O, S or NR8,

: that Y3 represents NR8, then R8 and R6 together with the nitrogen atom to which they are linked may form a 5- to 7-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which cycle may also include one of the groups C(=0) and C(=S),

represents an hydrogen, Ci-C8-aikyl, C3-C8-cycloaIkyl, Ci-C8-haiogenoalkyl comprising up to 9 chlorine, bromine or iodine atoms which can be the same or different, Cr(yalkaiyl, C2-C8-alkynyl, C3-C8-cycloalkyi-Ci-C8-a ikyl, C2-C8-aikenyl-CrCraikyi, Cz-Cg-alkynyl-Ci-Cg-alkyl, C3-C8- halogenocycloalkyi comprising up to 9 halogen atoms which can be the same or different, C3-C8- cycloalkenyl, Ci-C8-alkoxy-Ci-C8-alkyi, C3-C8-cycloalkoxy-Ci-C8-alkyi, Ci-C8-halogenoalkoxy-Cr C8-alkyl comprising up to 9 halogen atoms which can be the same or different, Ci-C8-alkylsulfanyi- Ci-C8-alkyl, Ci-C8-alkyiamino-C|-C8-alkyl, Ci-C8-haiogenoalkylamino-Ci-C8-alkyl comprising up to 9 halogen atoms which can be the same or different, C3- C^cycloalkylamino-C i - Cs-alkyl, Ci-C8- trialkylsilyl, C i - C8-triaIkylsilyl-C i -C8-alkyl, an aryl-C3-C8-cycloalkyi which can be substituted by up to 5 groups Q, an aryl-C]-C8-alkyi which can be substituted by up to 5 groups Q, an heteroaryi-C]- C8-alkyl which can be substituted by up to 5 groups Q, Ci-C8-alkylcarbonyi, C i - C8-halogenoalkyl- carbonyl comprising up to 9 halogen atoms which can be the same or different, C3-Cr cycloalkycarbonyl, Ci-C8-alkoxycarbonyl, Ci-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C3-C7-cycloalky!oxycarbonyi, Ci-C8-alkyl- armnocarbonyl, di-(Ci-C8-alkyi)aminocarbonyl, or represents a 4 to 7 membered ring containing 1-3 heteroatoms selected from O, N or S. This ring could be aromatic, partially saturated or fully saturated and substituted by up to 5 groups Q,

represents the following group

R2 and R3, which can be the same or different independently of one another represent hydrogen, halogen, CN, H2, N02, Ci-Cralkyl, Ci-Cs-hydroxyalkyl, C3-C8-cycloalkyl, C3-Cg-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different Ci-Cs-halogenoaikyl comprising up to 9 halogen atoms which can be the same or different Cj-Cg-cycloalkyl-Ci-Cs-alkyl, C2-Cg- alkenyl, Q-Cg-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, Cz-Cg-alkynyl, C2-C8-alkenyi-CrC8-alkyi, C2-C8-alkynyl-Ci-C8-alkyi, C3-C8-halogeno- cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C3-C8-cycloalkenyi, Ci-C8-aIkoxy-CrC8-alkyl, Ci-C8-aU oxy-C2-C8-alkenyl, C C8-alkoxy-C C8-alkynyl, C3-C8-cyclo- alkoxy-Ci-C8-alkyi, CrC8-haiogenoalkoxy-C|-C8-alkyl comprising up to 9 halogen atoms which can be the same or different Ci-C8-alkylsulfanyl-Ci-C8-alkyl, Ci-C8-a!kylsulfmyl-Ci-C8-alkyl, Cr C8-alkylsuifonyi-Ci-C8~alkyl, amino-Ci-C8-alkyl, Ci-C8-alkyiamino-Ci-C8-alkyi, di-(CrC8-alkyl)- amino-Ci-C8-alkyl, Ci-C8-halogenoalkyiamino-Ci-C8-alkyl comprising up to 9 halogen atoms which can be the same or different C3 - C s-cy cloalkylamino- C 1 - C g-alky 1, C 1 -Cs-trialkylsilyl- C 1 -C 8-alkyl, Ci-Cs-trialkylsilyl, phenyl which can be substituted by up to 5 groups Q, phenyl-C2-C4-alkynyl, which can be substituted in the phenyl moiety by up to 5 groups Q,

R " and R3 also together with the carbon atom to which they are linked can form a CrCrcycloalkyl, which may be substituted by 1 to 4 identical or different substituents selected from by halogen, OH, Ci-Gralkyl,
Ci-C"4-alkoxy, Ci-C4-alkylthio or phenyl, or can form a Ci-Cio-bicycloalkyl, a 2,3-dihydro-lH-indene-l-yi or a decahydronaphthalenyl,

R4 represents an aryl or a heterocycle E 1 to E 144:


-65-


E 101 E 102 E 103 E 104 E 105

R4 also represents hydrogen or halogen when n represents 1, 2, 3 or 4,

R5 represents hydrogen, OH, NH2, CN, Ci-Cralkyl, Ca-Cs-cycloalkyl, Ci-Cs-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, Ca-Crcycloalkyi-Ci-Cralkyi, QrCr alkenyl-d-Cs-alkyl, C2-C8-aIkynyl-Ci -C g-alkyl, halogeno-Ca-Cs-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, CB-Cs-cycloalkenyi, Ci-Cs-aikoxy-Cj-Cs-alkyl, C3- Cs-cycioaikoxy-Ci-Cralkyl, Ci-Cg-halogenoalkoxy-Ci-Cg-alkyl comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-aikyisuifanyi-Ci-Cs-alkyl, Ci-Cs-aSJsylamino-Ci-Cs-alkyl, Ci-C8-halogenoalkylamino-Ci-C8-alkyl comprising up to 9 halogen atoms which can be the same or different, C3-Crcycloalkylamino-Ci-Cralkyl, Ci -C rtrialkylsilyl-C 1 - C alkyl, an aryl which can be substituted by up to 5 groups Q, an aryl-C V(VaIkyl which can be substituted by up to 5 groups Q, an aryl-C3-C8-cycloalkyl which can be substituted by up to 5 groups Q; Ci-Cg-alkoxy, C3-C8- cycloalkoxy, Ci-Cg-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, Ca-Cs-cycloalkyl-Ci-Cg-alkoxy, Cz-Cs-alkenyl-Ci-Cs-alkoxy, C2-C8-aIkynyl-Ci-C8-aIkoxy, halogeno-C3-C8-cycioalkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -Ce-alkoxy-C 1 -Cr alkoxy, Cs-Cs-cycloalkoxy-Ci-Cs-alkoxy, C 1 -Cr halogenoalkoxy-C 1 - Cr alkoxy comprising up to 9 halogen atoms which can be the same or different, Cj-Cs-aikylsulfanyl-Ci-Cs- alkoxy, Ci-Cs-alkylamino-Ci-Cs-alkoxy, Ci-Cs-halogenoalkylamino-Ci-Cs-alkoxy comprising up to 9 halogen atoms which can be the same or different, C3- Cs-cycloalkylamino-C 1 - Cr alkoxy, Cj-Cr trialkylsilyl-Ci-C8-alkoxy, an aiyloxy which can be substituted by up to 5 groups Q, an aryl-Ci-Cs- alkoxy which can be substituted by up to 5 groups Q, an aryl-C3-C8-cycloalkoxy which can be substituted by up to 5 groups Q, Ci-Cs-alkyiamino, (Ci-C8-alkyl)carbonylamino, C3-C8- cycloalkylamino, Ci-Cs-halogenoalkylamino comprising up to 9 halogen atoms which can be the same or different, Cs-Cs-cycloalkyl-Ci-Cs-alkylarmno, C2-C r alkenyl-C 1 -Cs-alkylamino, C2-C8- alkynyl-Ci-C8-alkylamino, halogeno-Ca-Cg-cycloalkylamino comprising u to 9 halogen atoms which can be the same or different, arylamino which can be substituted by up to 5 groups Q, benzyl- ami no which can be substituted by up to 5 groups Q,

R" represents hydrogen, Cj-Cs-alkyl, Cj-Crcycloalkyl, Cj-Cs-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, Cs-Cs-cycloalkyl-Ci-Cs-alkyl,
C2-C8- alkynyl, C2-C8-aIkenyl-Ci-Cralkyl, C2-C8-aSkynyl-Ci-C8-alkyl, halogeno-C3-C8-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, Cj-Cg-cycloalkenyl, Ci-CValkoxy- Ci-C8-alkyl, Ca-Cs-cycloaikoxy-Ci-Cs-alkyl, Ci-Cs-halogenoalkoxy-Ci-Cs-aikyl comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkylsulfanyi-Ci-Cs-alkyl, Ci-Cs- alkylamino-Ci-Cs-a!kyi, Ci-Cs-halogenoalkylamino-Ci-Cs-alkyl comprising up to 9 halogen atoms which can be the same or different, C3- Cs-cycloalkylamino-C 1 - Cs-alkyl, Ci-Cg-trialkylsilyi-Ci-Cs- alkyl, phenyl or naphthyi, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q,

R6 also represents CN, if R is R , t is 0 and Y3 is a bond,

R represents hydrogen, OH, Ci-Cg-alkyl, Cs-Cs-cycioalkyi, Ci-Cs-haiogenoalkyi comprising up to 9 halogen atoms which can be the same or different, Cs-Crcycloalkyl-Ci-Cs-alkyl, C2-Cg-alkenyl- C 1 - C8-alkyi, C2-C8-alkynyi-Ci-C8-alkyl, Ci-Cg-halogeno-Cs-Cs-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, Cs-Cg-cycloalkenyl, Ci-Cg-alkoxy-Cj-Cg-aikyl, C3-C8- cycloalkoxy-Ci-C8-alkyl, Ci-Cs-halogenoaikoxy-Ci-Cs-alkyi comprising up to 9 halogen atoms which can be the same or different, C 1 -Cs-alkylsulfanyl-C 1 - C alkyl, Ci-Cs-alkyiamino-Ci-Cs-alkyi, CrCrhalogenoalkylamino-Ci-Cralkyl comprising up to 9 halogen atoms which can be the same or different, C C -cycloalkylamino- C i -C r alkyl, C i -Crtrialkylsiryl-Ci -C r alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; Q-Cralkoxy, Ca-Cg-cycioalkoxy, C j -C -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C3-CrcycloaIkyl-Ci-Cralkoxy, C2- Cg-alkenyl- C i -C r alkoxy, C2-Cralkynyl-Ci-Cr alkoxy, Ci-Cs-haiogeno-Cs-Cs-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C3-C g-cycloalkenyloxy, C i - C alkoxy-C i -C r alkoxy, C3-Crcycloalkoxy-Ci-Cr alkoxy, Ci-Cs-halogenoalkoxy-Ci-Cs-alkoxy comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkylsulfanyl-Ci-Cg-alkoxy, C i -C g-alkylamino-C i -Cr alkoxy, Cj-Cr halogenoalkylamino-Ci-Cralkoxy comprising up to 9 halogen atoms which can be the same or different, C3-C g-cycloalkylamino- C 1 -C r alkoxy, Ci-Cg-trialkylsilyl-Ci-Cg-aikoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q,

R8 represents hydrogen, OH, Ci-Cg-aikyl, C3-C8-cycioalkyl, Ci-Cg-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, Cj-Cg-cycloalkyl-Ci-Cs-alky , C2-Cs-alkenyl-Ci- ( alkyl, QrC g-alkynyl-C 1 - Chalky 1, C3-C8-halogenocycioaSkyi comprising up to 9 halogen atoms which can be the same or different, Cs-Crcycloalkenyi, Q -C g-alkoxy-C 1 -Cs-alkyl, Cj-Cs-cyclo- alkoxy-C 1 - Chalky 1, Ci-Cg-halogenoalkoxy-Ci-Cs-alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -Cr alkylsulfany 1-C 1 - Cr alkyl, Ci-Cs-alkyiamino-Ci-Cs-alkyl, Ci-Cg- halogenoalkylamino-Ci-Cs-alkyi comprising up to 9 halogen atoms which can be the same or different, C3-C8-cycioalkylamino-Ci-C8-alkyi, C 1 -C g-trialkylsilyl- Q - Cr alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; Ci-Cg-alkoxy, C3- Crcycloalkoxy, Ci-Cs-halogenoaikoxy comprising up to 9 halogen atoms which can be the same or different, Cs-Cs-cycioalkyl-Ci-Cg-alkoxy, CrCg-alkenyl-Cj-Cra koxy, Qz-C g-alkynyl-C 1 - C alkoxy, halogeno-C3-C8-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C3-C8-cycloalkenyloxy, C 1 - C alkoxy-C 1 -C r alkoxy, C3-CrcycloaIkoxy-Ci-Cr alkoxy, Ci-Cg-halo- genoalkoxy-Ci-Cs-alkoxy comprising up to 9 halogen atoms which can be the same or different, C - Cralkylsulfanyl-Ci-Cralkoxy, C 1 - Cg-alkylamino- Ci - Cg-alkoxy, Ci-Cs-halogenoaikyiamino-Ci-Cs- alkoxy comprising up to 9 halogen atoms which can be the same or different, Cs-Crcyclo- alkylamino- C 1 - C alkoxy , Ci-Cs-trialkylsilyl-Ci-Cg-alkoxy, phenyloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q,

Q which can be the same or different, independently represents halogen, CN, NO2, Ci-Cs-alkyl, d- Cg- alkoxy, C 1 - C r lkylsulfany 1, C 1 - C s-halogenoalkyl comprising u to 9 halogen atoms which can be the same or, Ci-Cs-haiogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(Cj-C8)aikyisiiyl or tri (C 1 - Cs)alkylsilyl- C 1 - Cr alkyl, or two vicinal substituents Q may be -OCH20-, -OCF20-, -0(CH2)20-, -0(CF2)20- or - =CH-S-,

Z1, Z2, Z3, Z4 /: , Z6, Z7, Z8, Z9, Z10 and Z11 which can be the same or different, independently of one another represent hydrogen, halogen, N02, CN, OH, SH, NH2, SF5, Ci-Cs-alkyl, Ci-Cs-halogenoaikyi comprising up to 9 halogen atoms which can be the same or different different and optionally in addition one hydroxy group, Ci-Cg-alkylamino, di-Ci-Cg-alkyiamino, Ci-Cg-alkoxy, Ci-Cr haiogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, Ci-Cg-

alkoxy-Ci-Cs-alkyl, Ci-Cs-alkylsulfanyl, C i -C 8-halogenoalkylsulfany 1 comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkenyl, C2- Cs-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C2-Cg-aIkynyl, Ci-Cs-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C2-CraIkenyloxy, Q-C halogenoalkenyioxy comprising up to 9 halogen atoms which can be the same or different, C2-C8- alkynyloxy, C2-C halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C2-Cralkenylsulfanyl, C2- C alkynylsulfanyl, C3-C7-cycloalkyl, C3-Crcycloalkyl-Ci-Cr alkyl, Cs-C -halogenocycloaSkyi comprising up to 9 halogen atoms which can be the same or different, formyl, formyloxy, formylamino, carbamoyl, -hydroxycarbamoyl, (hydroxyimino)-Ci-Cs- alkyl, Ci-Cralkylcarbonyl, Ci-Cs-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, (CrCr ycloalkyl)carbonyl, Ci-Cs-alkylcarbamoyl, di-Ci-Cg- alkylcarbamoyl, N-Ci-Cg-alkoxycarbamoyi, Ci-Cs-alkoxycarbamoyi, N-C 1 -Cg-alkyl-C 1 -Cr alkoxycarbamoyl, Ci-Cs-aSkoxycarbonyi, Ci-Crhalogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkylaminocarbonyl, di- (C 1 - C alkyl)aminocar- bonyl, Q-Cs-alkyicarbonyioxy, Ci-Cg-haiogenoalkyicarbonyloxy comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkylcarbonylamino, Ci-Crhalogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C 1 -C r alkylaminocarbonyloxy, di-(C 1 - Cr alkyl) aminocarbonyloxy, Ci-Cs-alkoxycarbonyloxy, Ci-Cs-alkylsulphinyl, Ci-Cg-halo- genoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-ai- kylsulphonyl, Ci-Crhalogenoalkylsuiphonyl comprising up to 9 halogen atoms which can be the same or different, C 1 - Cg-alkoxyimino, (C 1 -C -alkylimino)- C 1 -C 8-aIkyl, (Ci-Cralkoxyimino)-Ci-Cr alkyl, ( C 1 - C r alkeny loxy imino) -C 1 -C 8-aIkyl, (C2-Cralkynyloxyimino)-Ci-Cs-alkyl, a (benzyloxy- imino)-Ci-C8-alkyl, tri(Ci-C8~alkyl)silyl, tri (C 1 - C alkyl) silyl-C 1 - Cs-alky 1, benzyloxy which can be substituted by up to 5 groups Q, benzylsulfanyl which can be substituted by up to 5 groups Q, ben- zylamino which can be substituted by up to 5 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylsulfanyl which can be substituted by up to 5 groups Q, phenylmethyiene which can be substituted by up to 5 groups Q, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form a 5- or 6-membered, saturated or unsaturated, carbo- or heterocycie comprising up to 3 heteroatoms, which can be substituted by up to four groups Q which can be the same or different and the other substituents Z are as herein-described,

or two geminai subsitutens Z together with the carbon atom to which they are linked could also be fused to represent C(=0); C(=S), Ca-Cg-cycioalkyl;

G1 and G2 which can be the same or different, independently of one another represent hydrogen, CN, OH, N¾, Ci-Cg-alkyl, Ci-Crhaiogenoaikyl comprising up to 9 halogen atoms which can be the same or different, Cj-Cs-aSkyiamino, di-Q-Cs-alkylamino, Ci-Ce-alkoxy, Cj-Cs-haiogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, Ci-Cs-alkoxy-Ci-Cs-altyl, C2-C8-aikenyl, C2-C8-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C Cir alkynyl, C^-Cs-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C2-C8-alkenyloxy, C2-Cs-halogenoalkenyloxy comprising up to 9 halogen atoms which can be

the same or different, C2-C8-aIkynyloxy, C2-C8-halogenoatkynyloxy comprising up to 9 halogen atoms which can be the same or different, C3-Crcycloalkyl, C3-C7-cycloalkyl-C]-C8-alkyl, C3-C7- halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, carbamoyl, (hydroxyimino)-Ci-Cg-alkyl, C]-C8-alkyicarbonyl, CrCs-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8-alkylcarbamoyl, Ci-C8- alkoxycarbonyl, Ci-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C 1 - Cs-alkylaminocarbonyl, di-Ci-C8-alkylaminocarbonyl, Ci-C8-alkyisuiphonyi, Ci-C8-halogenoalkyisuiphonyl comprising up to 9 halogen atoms which can be the same or different, (Ci-Cg-aIkoxyimino)-Ci-C8-aIkyl, (C 1 - C lkenyloxyimi no) - C 1 - C alky 1,

Ci-Cg-alkyl, a (benzyloxyimino)-Ci-C8-alkyl, tri(CrC8-aIkyl)silyl, tri(Ci-C8-aIkyI)silyl-CrC8-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenyimethylene which can be substituted by up to 5 groups Q,

as well as salts, N-oxides, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof.

2. Composition for controlling unwanted microorganisms or insects, characterized in that they comprise at least one cyanoenamine of the formula (I) according to Claim 1, in addition to extenders and/or surfactants.

3. Use of cyanoenamines of the formula (I) according to Claim 1 for controlling unwanted microorganisms and insects.

4. Method for controlling unwanted microorganisms, characterized in that cyanoenamines of the formula (I) according to Claim 1 are applied to the microorganisms and/or their habitat.

5. Process for preparing compositions for controlling unwanted microorganisms, characterized in that cyanoenamines of the formula (I) according to Claim 1 are mixed with extenders and/or surfactants.

6. Use of cyanoenamines of the formula (1) according to Claim 1 for treating transgenic plants.