Claims
- 1. A compound of the formula ##STR16## in which R is halogen, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkoxy-C.sub.1-4 alkyl, phenoxy-C.sub.1-4 alkyl, phenylthio-C.sub.1-4 alkyl, C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, optionally C.sub.1-4 alkyl-substituted C.sub.3-6 cycloalkyl-carbonyloxy-C.sub.1-4 alkyl, benzoyl-C.sub.1-4 -alkyl, phenyl-C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenoxy or one of the groups ( a ) to ( e )
- R.sup.1 CH.dbd.CH (a)
- R.sup.2 R.sup.3 NCH.sub.2 (b)
- R.sup.4 R.sup.5 C.dbd.NOCH.sub.2 (c)
- R.sup.6 N.dbd.CH (d)
- R.sup.7 R.sup.8 N--N.dbd.CH (e),
- R.sup.1 is phenyl,
- R.sup.2 and R.sup.3 independently of one another are hydrogen,
- C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl or phenyl,
- or R.sup.2 and R.sup.3 together with the nitrogen atom to which they are bonded form a 5- or 6-membered ring which may contain an oxygen or sulfur atom,
- R.sup.4 and R.sup.5 independently of one another are hydrogen,
- C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, C.sub.1-4 alkylthio-C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, phenyl, C.sub.1-4 alkoxy or benzoyl,
- or
- R.sup.4 and R.sup.5 together with the carbon atom to which they are bonded form (1) a 5- or 6-membered heterocyclic ring having up to two hereto atoms selected from N and S or (2) a 5- or 6- membered carbocyclic ring to which one or two benzene rings may be fused,
- R.sup.6 is phenyl, C.sub.1-4 alkoxy, phenyl-C.sub.1-4 alkoxy or C.sub.3 or 4 alkenyloxy,
- and
- R.sup.7 and R.sup.8 independently of one another are hydrogen,
- C.sub.1-4 alkyl, phenyl, or phenylsulfonyl;
- the foregoing phenyl substituents being unsubstituted or substituted by a substituent selected from the group consisting of halogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkylthio-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, phenyl-C.sub.1-4 alkoxy, C.sub.1-4 alkenyloxy, phenoxy, C.sub.1-4 alkylthio, C.sub.1-4 cycloalkyl-C.sub.1-4 alkylthio, nitro and tri(C.sub.1-4 alkyl)silyl.
- 2. A compound as claimed in claim 1, in which the substituent R is in the 5-position of the benzo[b]thiophene ring.
- 3. A compound as claimed in claim 22 in which halogen, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, phenoxy-C.sub.1-4 alkyl, phenylthio-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenoxy or one of the groups (a) to (d), R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 2, and R.sup.4 and R.sup.5 independently of one another are hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl or phenyl and R.sup.6 is phenyl.
- 4. A compound as claimed in claim 3, selected from amongst
- Methyl .alpha.-(5-(.alpha.-methyl-m-trifluoromethylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-[n-propyl]-benzylideneaminooxy-methyl)-3-benzo[b ]thienyl}-g-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-cyclopropyl-4-chlorobenzylideneaminooxymethyl)-3-benzo[b ]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-methoxy-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-ethoxy-3-benzo[b]thienyl}-13-methoxyacrylate,
- methyl .alpha.-{5-[(.alpha.-phenylethyl)methylaminomethyl]-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(dicyclopropylmethylideneaminooxymethyl)-3-benzo[b ]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-cyclopropyl-m-trifluoromethylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate.
- 5. A compound as claimed in claim 1, selected from amongst:
- methyl .alpha.-{5-(.alpha.-cyclopropylbenzylideneaminooxymethyl)-3-benzo[b ]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-[g-methyl-.alpha.-(2-pyridyl)-propylideneaminooxymethyl]-3-benzo[b ]thienyl}-.beta.-methoxyacrylate and
- methyl .alpha.-{5-(2-isopropyl-4-methyl-2,5-dihydrothiazol-5-ylideneamino oxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate.
- 6. A compound as claimed in claim 3, in which the substituent R is in the 5-position of the benzo[b]thiophene ring.
- 7. The compound methyl .alpha.-{5-(.alpha.-methyl-m-[.alpha.,.alpha.,.alpha.-trifluoro-m-tolyloxy]-benzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate.
- 8. A fungicidal composition which contains an effective amount of a compound as defined in claim 1 and formulation auxiliaries.
- 9. A fungicidal composition as claimed in 8, which contains an effective amount of a compound selected from the group consisting of:
- methyl .alpha.-{5-(.alpha.-methyl-m-trifluoromethylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-[n-propyl]-benzylideneaminooxy-methyl]-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-cyclopropyl-4-chlorobenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-methoxy-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-ethoxy-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-[(.alpha.-phenylethyl)methylaminomethyl]-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(dicyclopropylmethylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(.alpha.-cyclopropyl-m-trifluoromethylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- and also formulation auxiliaries.
- 10. A fungicidal composition as claimed in claim 8, which contains an effective amount of a compound selected from the group consisting of:
- methyl .alpha.-{5-(.alpha.-cyclopropylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- methyl .alpha.-{5-(2-isopropyl-4-methyl-2,5-dihydrothiazol-5-ylidene aminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate,
- and also formulation auxiliaries.
- 11. A method of controlling fungi in agriculture and in horticulture, which comprises treating the goods to be protected with an effective amount of a compound as claimed in claim 1.
- 12. A method of controlling fungi in agriculture and in horticulture, which comprises treating the goods to be protected with an effective amount of a compound as claimed in claim 1.
- 13. A method according to claim 11 wherein the compound is a compound wherein the substituent R is in the 5-position of the benzo[b]thiophene ring.
- 14. A method according to claim 11 wherein the compound is a compound selected from the group consisting of methyl .alpha.-{5-(.alpha.-cyclopropylbenzylideneaminooxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate, and methyl .alpha.-{5-(2-isopropyl-4-methyl-2,5-dihydrothiazol-5-ylideneamino oxymethyl)-3-benzo[b]thienyl}-.beta.-methoxyacrylate.
- 15. A method for controlling fungi in agriculture or horticulture which comprises treating goods to be protected with a composition as defined in claim 10.
- 16. A method for controlling fungi in agriculture or horticulture which comprises treating goods to be protected with a composition as defined in claim 10.
- 17. A method for controlling fungi in agriculture or horticulture which comprises treating goods to be protected with an effective amount of a compound as defined in claim 4.
- 18. A method for controlling fungi in agriculture or horticulture which comprises treating goods to be protected with an effective amount of a composition as defined in claim 9.
Priority Claims (1)
Number |
Date |
Country |
Kind |
4499/89-6 |
Dec 1989 |
CHX |
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Parent Case Info
This application is a continuation of now abandoned application Ser. No. 07/802,742, filed Dec. 5, 1991, now abandoned, which is a division of now abandoned application Ser. No. 07/625,765, filed Dec. 13, 1990, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4816476 |
Klaus et al. |
Mar 1989 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
0243014 |
Oct 1987 |
EPX |
0342459 |
Nov 1989 |
EPX |
Non-Patent Literature Citations (6)
Entry |
Schultz et al., Chemical Abstracts, vol. 112 (1990), Abstract No. 216453d. |
Schultz et al., Chemical Abstracts, vol. 113 (1990), Abstract No. 152433h. |
Beautement et al., Chemical Abstracts, vol. 111 (1989) Abstract No. 114868e. |
Clough et al., Chemical Abstracts, vol. 107 (1987) Abstract No. 6939n. |
Clough et al., Chemical Abstracts, vol. 109 (1988), Abstract No. 50255b. |
Nannini et al., Chemical Abstracts, vol. 96 (1982) Abstract No. 68717b. |
Divisions (1)
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Number |
Date |
Country |
Parent |
625765 |
Dec 1990 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
802742 |
Dec 1991 |
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