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US 8,569,509 B2Granted
Thiazole-4-carboxylic acid esters and thioesters as plant protection agents
AssigneeBayer Intellectual Property GmbH
InventorsPierre Cristau, Stefan Herrmann, Nicola Rahn, Arnd Voerste, Ulrike Wachendorff-Neumann, Tomoki Tsuchiya
Life of this patent
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Abstract
The use of thiazole-4-carboxylic esters and thioesters of the formula (I) in which R1, R2, R3, R4, R5, R6, R7, Y1, Y2, Y3, W, X and G have the meanings given in the description, and also of agrochemically active salts thereof, as fungicides.
Claims7
A compound of the formula (I)
- in which the symbols have the following meanings:
- R1 and R3 independently of one another are H, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, halogen, hydroxyl, cyano or phenyl,
- R2 is H, phenyl, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, formyl, CR8═NOR9, halogen, hydroxyl, cyano or NR10R11,
- or
- R1 and R2 or R2 and R3 together with the carbon atoms to which they are attached form a 5- to 7-membered unsubstituted or substituted, partially saturated or unsaturated cycle which may contain up to two further heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent,
- possible substituents independently of one another being selected from the group consisting of C1-C4-alkyl, hydroxyl, oxo and halogen,
- R4 and R5 independently of one another are H, C1-C4-alkyl, C3-C6-cycloalkyl or
- or
- R4 and R5 together with the carbon atom to which they are attached form a 3- to 6-membered saturated cycle which may contain up to two heteroatoms selected from the group consisting of N and O, where two oxygen atoms are not adjacent,
- Y1, and Y2 are oxygen,
- Y3 is sulfur or oxygen,
- X is a direct bond or an unsubstituted or substituted C1- to C3-carbon chain, where the carbon atoms carry, independently of one another, H, methyl or oxo as substituents,
- W is an unsubstituted or substituted C1- to C3-carbon chain, where the carbon atoms carry, independently of one another, H, methyl or oxo as substituents,
- R6 is H, C1-C4-alkyl, C1-C4-haloalkyl, CONR10R11, (C1-C4-alkoxy)carbonyl, COOH, NR10R11, halogen or cyano,
- G is (C(R12)2)m,
- where m=0 to 6,
- R7 is unsubstituted or substituted C5-C10-alkyl, C2-C16-alkenyl, C2-C16-alkynyl, C3-C15-cycloalkyl, C5-C15-cycloalkenyl, C3-C15-heterocyclyl, aryl, hetaryl or Si(C1-C4-alkyl)3,
- possible substituents independently of one another are selected from:
- halogen, cyano, nitro, nitroso, C1-C4-alkyl, C1-C4-haloalkyl, aryl-C1-C3-alkyl, aryl-C1-C3-haloalkyl, hydroxyl, oxo, C1-C4-alkoxy, O(C1-C6-alkyl)mOC1-C6-alkyl, O—C3-C6-cycloalkyl, O-phenyl, C1-C4-haloalkoxy, SH, C1-C4-thioalkyl, C1-C4-thiohaloalkyl, S-phenyl, SO2—C1-C6-alkyl, SO2—C1-C6-haloalkyl, SO—C1-C6-alkyl, SO—C1-C6-haloalkyl, CO2H, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, formyl, CR8═NOR9, CONR10R11, (C1-C4-alkoxy)carbonyl, COOH, NR10R11, cyclopropylamino, CH2COCH3, (CH2)mO—C1-C6-alkyl, CH2OH, CH2SMe, (CH2)2SMe, C3-C6-cycloalkyl, 1-methoxycyclopropyl, 1-chlorocyclopropyl, cyclohexylmethyl, C2-C6-alkenyl, C2-C6-alkynyl, Si(C1-C4-alkyl)3, phenyl or benzyl,
- or
- two adjacent substituents form an optionally methyl- or halogen-substituted dioxolane or dioxane ring,
- R8, R9, R10, and R11 independently of one another are H, C1-C3-alkyl or cyclopropyl,
- or
- R10 and R11 together with the nitrogen atom to which they are attached form a 3- to 6-membered saturated cycle which may contain up to one further heteroatom selected from the group consisting of N and O,
- R12 is identical or different independently of one another H, chlorine, fluorine, C1-C3-alkyl, C1-C3-alkoxy, C3-C6-cycloalkyl or trifluoromethyl,
- or
- two or four R12, in each case on two adjacent carbon atoms, are direct bonds,
- or an agrochemically active salt thereof.
25 more elements
Dependencies are inferred from the claim text.