Agents for combating plant pests

Abstract

The present invention relates to compositions for controlling plant pests, which contain the compound of the formula (I) ##STR00001##
in a mixture with fungicidally active compounds, except for cyclopropylcarboxamide derivatives and azolylmethylcycloalkanes.

Claims

1. A composition comprising the compound of the general formula (I) ##STR00118## and metalaxyl.

2. The composition according to claim 1, wherein the composition comprises from 0.1 to 10 parts by weight of metalaxyl per part by weight of active compound of the formula (I).

3. A process for controlling fungi or insects, characterized in that active compound combinations according to claim 1 are allowed to act on the fungi, insects and/or their habitat.

4. A process for preparing a composition according to claim 1, comprising mixing the composition according to claim 1 with extenders and/or surfactants.

Description

EXAMPLE A

(1) Phaedon Larvae Test

(2) Solvent: 7 parts by weight of dimethylformamide

(3) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(4) To produce a suitable preparation of active compound, 1 part by weight of an active compound or an active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(5) Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the mustard beetle (Phaedon cochleariae) while the leaves are still moist.

(6) After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

(7) In this test, for example, the following active compound combinations according to the present invention show a synergistically increased activity compared to the individually applied active compounds:

(8) TABLE-US-00001 TABLE A (plant-damaging insects) Phaedon larvae test Active compound/active com- Active compound/active com- pound mixture pound mixture concentration in % Kill in % 0.00016 0.000032 20 0 0.1 0 formula (1) + kresoxim-methyl 0.00016 + 0.1 75

EXAMPLE B

(9) Plutella Test

(10) Solvent: 7 parts by weight of dimethylformamide

(11) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(12) To produce a suitable preparation of active compound, 1 part by weight of an active compound or an active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(13) Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the diamondback moth (Plutella xylostella) while the leaves are still moist.

(14) After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

(15) In this test, for example, the following active compound combinations according to the present invention show a synergistically increased activity compared to the individually applied active compounds:

(16) TABLE-US-00002 TABLE B (plant-damaging insects) Plutella test Active com- pound/active compound Kill Active compound/active compound mixture concen- in mixture tration in % % 0.0008 0 0.02 0 0.1 0 formula (I) + tebuconazole 0.0008 + 0.02 100 formula (II) + metalaxyl 0.0008 + 0.1 100

EXAMPLE C

(17) Heliothis virescens Test

(18) Solvent: 7 parts by weight of dimethylformamide

(19) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(20) To produce a suitable preparation of active compound, 1 part by weight of an active compound or an active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(21) Soya bean shoots (Glycine max) are treated by being dipped into the active compound preparation of the desired concentration and are populated with Heliothis virescens caterpillars while the leaves are still moist.

(22) After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

(23) In this test, for example, the following active compound combinations according to the present invention show a synergistically enhanced activity in comparison to the individually applied active compounds:

(24) TABLE-US-00003 TABLE C (plant-damaging insects) Heliothis virescens test Active com- pound/active compound Kill Active compound/active compound mixture concen- in mixture tration in % % 0.00016 50 0.0008 0 formula (I) + azoxystrobin 0.00016 + 0.0008 100

EXAMPLE D

(25) Nephotettix Test

(26) Solvent: 7 parts by weight of dimethylformamide

(27) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(28) To produce a suitable preparation of active compound, 1 part by weight of an active compound or an active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(29) Rice seedlings (Oryza sativa) are treated by being dipped into the active compound preparation of the desired concentration and are populated with the green rice leaf hopper (Nephotettix cincticeps) while the leaves are still moist.

(30) After the desired period of time, the kill in % is determined. 100% means that all the leaf hoppers have been killed; 0% means that none of the leaf hoppers have been killed.

(31) In this test, for example, the following active compound combinations according to the present invention show a synergistically enhanced activity in comparison to the individually applied active compounds:

(32) TABLE-US-00004 TABLE D (plant-damaging insects) Nephotettix test Active com- pound/active compound Kill Active compound/active compound mixture concen- in mixture tration in % % 0.00000128 0 0 0.1 0 formula (I) + metalaxyl 0.00000128 + 0.1 85

EXAMPLE E

(33) Critical Concentration Test/Soil Insects

(34) Test insect: Spodoptera frugiperda

(35) Solvent: 4 parts by weight of acetone

(36) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(37) To produce a suitable preparation of active compound, 1 part by weight of the active compound or the active compound mixture is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(38) The active compound preparation is mixed intimately with soil. Here, the concentration of the active compound in the preparation is almost irrelevant; only the amount by weight of active compound or active compound mixture per volume unit of soil, which is stated in ppm (mg/1), matters.

(39) Soil is filled into 0.5 l pots and these are allowed to stand at 20 C. Immediately after preparation, 3 pre-germinated maize corns are placed into each pot. After the maize corns have emerged, boring sleeves are placed onto the pots. 9 days after preparation, the maize is populated with the test insects. After a further 5 days, the kill in % is determined. 100% means that all test insects have been killed; 0% means that the number of insects which are still alive is the same as for the untreated control.

(40) In this test, for example, the following active compound combinations according to the present invention show a synergistically enhanced activity compared to the individually applied active compounds:

(41) TABLE-US-00005 TABLE E Spodoptera frugiperda test Active com- pound/active compound Kill Active compound/active compound mixture concen- in mixture tration in ppm % 1.25 0.60 0.30 100 98 50 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 formula (I) + tebuconazole 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00 80 formula (I) + triadimenol 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00 50 formula (I) + bitertanol 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00 80 formula (I) + fenpiclonil 1.25 + 20.00 100 0.60 + 20.00 90 0.30 + 20.00 80 formula (I) + azoxystrobin 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00 0 formula (I) + metalaxyl 1.25 + 20.00 100 0.60 + 20.00 95 0.30 + 20.00 0 formula (I) + cyproconazol 1.25 + 20.00 100 0.60 + 20.00 50 0.30 + 20.00 0 formula (I) + propiconazole 1.25 + 20.00 100 0.60 + 20.00 90 0.30 + 20.00 70

EXAMPLE F

(42) Critical Concentration Test/Root-Systemic Action

(43) Test insect: Phaedon cochleariae larvae

(44) Solvent: 4 parts by weight of acetone

(45) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(46) To produce a suitable preparation of active compound, 1 part by weight of the active compound or the active compound mixture is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(47) The active compound preparation is mixed intimately with soil. Here, the concentration of the active compound in the preparation is almost irrelevant; only the amount by weight of active compound or active compound mixture per volume unit of soil, which is stated in ppm (mg/l), matters.

(48) Soil is filled into 250 ml pots and these are planted with cabbage (Brassica oleracea). The active compound or the active compound combination can thus be taken up by the plant roots from the soil and transported into the leaves.

(49) After 7 days, the leaves are populated with the abovementioned test animals. After a further 3 days, the kill in % is determined. 100% means that all test insects have been killed; 0% means that the number of insects which are still alive is the same as in the untreated control.

(50) In this test, for example, the following active compound combinations according to the present invention show a synergistically enhanced activity compared to the individually applied active compounds:

(51) TABLE-US-00006 TABLE F Phaedon cochleariae test Active com- pound/active compound Kill Active compound/active compound mixture concen- in mixture tration in ppm % 0 1.25 0.60 0.30 100 80 50 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 20.00 0 formula (I) + tebuconazole 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00 80 formula (I) + triadimenol 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00 100 formula (I) + bitertanol 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00 70 formula (I) + fenpiclonil 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00 70 formula (I) + azoxystrobin 1.25 + 20.00 100 0.60 + 20.00 90 0.30 + 20.00 50 formula (I) + metalaxyl 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00 50 formula (I) + propiconazole 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00 90

EXAMPLE G

(52) Formula for the Calculation of the Efficacy of a Combination of Two Active Compounds

(53) The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds 15, pages 20-22, 1967):

(54) if

(55) X is the efficacy, expressed in % of the untreated control, when applying the active compound A at an application rate of m g/ha, Y is the efficacy, expressed in % of the untreated control, when applying the active compound B at an application rate of n g/ha, E is the efficacy, expressed in % of the untreated control, when applying the active compounds A and B at application rates of m and n g/ha,
then

(56) $E=X+Y-\frac{XY}{100}.$

(57) If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the formula set out above.

(58) Phytophthora Test (Tomato)/Protective

(59) Solvent: 47 parts by weight of acetone

(60) Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

(61) To produce a suitable preparation of active compound, 1 part by weight of the active compound or the active compound mixture is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(62) To test for protective activity, young plants are sprayed with the commercial active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at approximately 20 C. and 100% relative atmospheric humidity.

(63) Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(64) The table below shows unambiguously that the activity which was found of the active compound combinations according to the invention is greater than the calculated efficacy (see above), i.e., a synergistic effect is present.

(65) TABLE-US-00007 TABLE G Phytophthora test (tomato)/protective Effi- Active com- cacy pound/active in % Active compound/active compound mix- calcula- compound mixture ture in g/ha ted/found 500 51 500 5 formula (I) + propiconazole 500 + 500 53/69 0 500 55 500 0 formula (I) + triadimenol 500 + 500 55/63 50 19 50 42 formula (I) + metalaxyl 50 + 50 53/68

EXAMPLE H

(66) Sphaerotheca Test (Cucumber)/Protective

(67) Solvent: 47 parts by weight of acetone

(68) Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

(69) To produce a suitable preparation of active compound, 1 part by weight of the active compound or the active compound mixture is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(70) To test for protective activity, young plants are sprayed with the commercial active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in an incubation cabin at approximately 20 C. and 100% relative atmospheric humidity.

(71) Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(72) The table below shows unambiguously that the activity which was found of the active compound combinations according to the invention is greater than the calculated efficacy (see above), i.e., a synergistic effect is present.

(73) TABLE-US-00008 TABLE H Sphaerotheca test (cucumber)/protective Effi- Active com- cacy pound/active in % Active compound/active compound mix- calcula- compound mixture ture in g/ha ted/found 10 0 10 70 formula (I) + cyproconazole 10 + 10 70/80 500 0 500 50 formula (I) + fenpiclonil 500 + 500 50/83

EXAMPLE I

(74) Botrytis Test (Bean)/Protective

(75) Solvent: 47 parts by weight of acetone

(76) Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

(77) To produce a suitable preparation of active compound, 1 part by weight of the active compound or the active compound mixture is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(78) To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, 2 small pieces of agar colonized by Botrytis cinerea are placed onto each leaf. The inoculated plants are placed in a dark chamber at approximately 20 C. and 100% relative atmospheric humidity.

(79) 2 days after the inoculation, the size of the disease spots on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(80) The table below shows unambiguously that the activity which was found of the active compound combinations according to the invention is greater than the calculated efficacy (see above), i.e., a synergistic effect is present.

(81) TABLE-US-00009 TABLE I Botrytris test (bean)/protective Effi- Active com- cacy pound/active in % Active compound/active compound mix- calcula- compound mixture ture in g/ha ted/found 10 0 10 40 formula (I) + fludioxonil 10 + 10 40/83 00 100 4 01 100 80 formula (I) + tebuconazole 100 + 100 81/94

EXAMPLE J

(82) Fusarium culmorum Test (Wheat)/Seed Treatment

(83) The active compounds are applied as a dry dressing. They are prepared by extending the active compound in question with ground minerals to give a finely pulverulent mixture which ensures even distribution on the surface of the seeds.

(84) For the dressing, the infected seeds are shaken with the dressing in a closed glass bottle for 3 minutes.

(85) 2100 seeds of the wheat are sown at a depth of 1 cm into standard soil, and the wheat is cultivated in a greenhouse at a temperature of approximately 18 C. and at a relative atmospheric humidity of approximately 95% in seed containers receiving 15 hours of light per day.

(86) The evaluation of the plants for symptoms is carried out approximately 3 weeks after sowding. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(87) TABLE-US-00010 TABLE J Fusarium culmorum test (wheat)/seed treatment Active com- Effi- pound/active cacy Active compound/active compound in compound mixture mixture in g/ha % 02 75 0 03 75 0 04 75 13.5 formula (I) + fludioxonil 37.5 + 37.5 38.5 formula (I) + triadimenol 37.5 + 37.5 30.5

EXAMPLE K

(88) Puccinia Test (Wheat)/Protective

(89) Solvent: 25 parts by weight of N,N-dimethylacetamide

(90) Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

(91) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(92) To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain in an incubation cabin at 20 C. and 100% relative atmospheric humidity for 48 hours.

(93) The plants are then placed in a greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of 80% to promote the development of rust pustules.

(94) Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(95) TABLE-US-00011 TABLE K Puccinia (wheat)/protective Active com- Effi- pound/active cacy Active compound/active compound in compound mixture mixture in g/ha % 05 18.75 0 06 18.75 13 formula (I) + triadimenol 9.375 + 9.375 63

EXAMPLE L

(96) Pyrenophora teres Test (Barley)/Protective

(97) Solvent: 25 parts by weight of N,N-dimethylacetamide

(98) Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

(99) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(100) To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabin at 20 C. and 100% relative atmospheric humidity for 48 hours.

(101) The plants are then placed in a greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80%.

(102) Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(103) TABLE-US-00012 TABLE L Pyrenophora teres test (barley)/protective Effi- Active com- cacy pound/active in % Active compound/active compound calcula- compound mixture mixture in g/ha ted/found 07 62.5 18.75 0 20 08 62.5 40 09 18.75 0 formula (I) + azoxystrobin 9.375 + 9.375 60 formula (I) + triazoxides 31.25 + 31.25 70

EXAMPLE M

(104) Erysiphe Test (Barley)/Protective

(105) Solvent: 25 parts by weight of N,N-dimethylacetamide

(106) Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

(107) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

(108) To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate:

(109) After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f. sp. hordei.

(110) The plants are placed in a greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

(111) Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

(112) TABLE-US-00013 TABLE M Erysiphe test (barley)/protective Effi- Active com- cacy pound/active in % Active compound/active compound calcula- compound mixture mixture in g/ha ted/found 0 62.5 0 62.5 0 formula (I) + kresoxim-methyl 31.25 + 31.25 75

EXAMPLE N

(113) Critical Concentration Test/Root Systemic Action

(114) Test insect: Spodoptera frugiperda

(115) Solvent: 4 parts by weight of acetone

(116) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(117) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

(118) The preparation of active compound is mixed intimately with soil. Here, the concentration of the active compound in the preparation is virtually immaterial; only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/1), matters. The soil is filled into 250 ml pots and these are allowed to stand at 20 C.

(119) Immediately after preparation, 3 maize corns are placed into each pot. 14 days after the preparation, the test insects are placed into an insect bracket and attached to the plant. 4 days after the infection, the efficacy of the active compound is determined in % by counting the dead and live test insects. The efficacy is 100% if all test insects have been killed; it is 0% if the same number of test insects is alive as in the untreated control.

(120) TABLE-US-00014 TABLE N Spodoptera frugiperda test Kill in % at active compound/active Active compound/active compound mixture compound mixture concentration in ppm 0.15 ppm = 50% 5.00 ppm = 0% compound according to formula (I) + 0.15 ppm + 5.00 ppm = 80% compound of group (49)

EXAMPLE O

(121) Critical Concentration Test/Soil Insects

(122) Test insect: Diabrotica balteatalarvae in the soil

(123) Solvent: 4 parts by weight of acetone

(124) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(125) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. Here, the concentration of the active compound in the preparation is almost irrelevant; only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/1), matters. The soil is filled into 0.5 l pots and these are allowed to stand at 20 C.

(126) Immediately after preparation, 5 maize corns are placed into each pot. After 3 days, the test insects are placed into the treated soil. After a further 7 days, the efficacy is determined. The efficacy is calculated from the number of maize plants which have emerged.

(127) Active compounds, application rates and results are shown in the table below:

(128) TABLE-US-00015 TABLE O Soil insecticides Diabrotica balteata-larvae in the soil Kill in % at active Active compound compound concen- (constitution) trations in ppm 0.15 ppm = 0% 20.00 ppm = 70% formula (I) + compound according to 0.15 ppm + 20.00 (50) ppm = 70%

(129) TABLE-US-00016 TABLE P Soil insecticides Diabrotica balteata-larvae in the soil Kill in % at active Active compound compound concen- (constitution) trations in ppm 0.30 ppm = 50% 20.00 ppm = 0% formula (I) + compound according to 0.15 ppm + 20.00 (48) ppm = 90%