Title of Invention

SYNERGISTIC HERBICIDAL MIXTURES

Abstract

A herbicidal composition having a synergestic effect of active components which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7- tetrahydropyrazolo-[ 1 ,5-a ]-pyridin-2-yl)-5-(methylpropargylamino )-4- pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIAOO51), tritluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-O61, azimsulfuron, propanil or imazosulfuron [Component (B)].

Full Text

The invention relates to novel mixtures of 1-(3-chloro-4,5.6,7-tetrahydropyrazolo-[1,5"a]-pyriclin-2-yl)-5-(methylpropargy(amino)-4-pyrazolylcarbonitrile and other herbicides, and to their use for controlling weeds in agricultural crops. The herbicidal action of 1-(3-chloro-4,5.6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyra2olylcarbonitrile has already been disclosed (DE OS 43 15 33a). Furthermore, it is knov^n that the use of mixtures of active substances can result in specific advantages, especially since the use of the individual active substances is unsatisfactory in most cases. It has now been found that herbicidal compositions which comprise, as active components, a mixture of 1-(3-chloro-4,5,6.7-tetrahydropyrazolo-[1,5"a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and another herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor. pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin. bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb. cinosulfuron. thenylchlor, cumyluron, MK243. naproanilide, anilofos, benfuresate, bifenox. CH-900, MCPA. nitrofen. oxadiazon, pendimethalin, simetryn, sulcotrione (IC1A0051), trifluralin, piperophos, pyributicarb. ethoxysulfuron,bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap. cyclosulfamuron, cyhalofop-butyl, NBA-061. azimsulfuron, propanil or imazosulfuron [Component (B)] exhibit an especially high herbicidal activity without losing the selective properties relative to agricultural crops such as rice and which in some cases even decidedly improve crop plant compatibility. With the exception of cumyluron and NBA-061, the active substances of Component (B) are known, for example, from The Pesticidal Manual. 10th Edition (1994), Brit. Crop Prot Council, London, and The Royal Soc. of Chem.. Cambridge. Cumyluron Itself has been described, inter alia, in Agrochem. Jpn.. 63, 18-19. 1993 (Konnai et al.) and NBA-061 In DE 504059. EP 612735 and EP 726259. Surprisingly, the herbicidal activity of the active substance combinations according to the invention by far exceeds the activity of the individual components and also the total of the individual components. Thus, a synergistic effect is present. For example, the active substance combinations according to the invention can be used for controlling the following plants: dicotyledon weeds of the genera Lindernia. Rotala, Mimosa, Heteranthera, Sinapis. Galium, Stellaria, Matricaria, Galinsoga. Chenopodium, Brassica, Urtica. Senecio, Amaranthus. Portulaca. Xanthium. Convolvulus, Ipomea. Polygonum, Sesbania, Cirsium, Carduus, Sonchus, Soianum. Lamium, Veronica, Abutilon. Datura and Viola, and monocotyledon weeds of the genera Alisma, Avena, Alopecurus. Echinochloa. Setaria, Scirpus, Panicum, Digitaria. Poa, Eleusine, Brachiaria, Lolium, Bromus. Cyperus, Agropyron, Sagittaria. Monochoria. Fimbristylis, Eieocharis, Ischaemum, Potamogeton. Eichhomia and Apera. The mixtures according to the invention are employed post-emergence by direct application, for example by spraying them onto the plants, or else pre-emergence by direct application into the paddy water, or by spraying. Selective application is possible in a series of crop plantings, of which rice is preferred. The rate of application is between 0.001 and 5 kg/ha for the total of the components in the mixture, depending on the intended purpose. The weight ratio of Component (A) to Component (B) in the mixture is between 1 : 0.1 and 1 : 100. preferably 1 : 0.5 and 1 : 50. If desired, the compositions according to the invention can also be used in the form of a mixture with other active substances, for example other crop protection chemicals or pesticides, depending on the intended purpose. Moreover, the intensity and speed of action can be enhanced for example by activity-promoting additives such as organic solvents, wetting agents and oils. Such additives may therefore allov/ the dosage rate of active substance to be reduced even further. It is expedient to employ the compositions according to the invention in the form of preparations such as powders, materials for spreading, granules, solutions, emulsions or suspensions with an addition of liquid and/or solid carriers or diluents and, if appropriate, tackifiers. wetting agents, emulsifiers and/or dispersants. Examples of suitable liquid carriers are aliphatic and aromatic hydrocarbons such as toluene, xylene, or else cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, and furthermore mineral oil fractions and vegetable oils. Suitable solid carriers are minerals, for example bentonite, silica gel. talc, kaolin, attapulgite. limestone and products of vegetable origin, for example meals. Examples of surfactants to be mentioned are calcium ligninsutfonate, polyethylene alkylphenyl ethers, naphthalenesulfonic acid and its salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfonates and unsubstituted benzenesulfonic acids and their salts. The amount of the active substances in the various preparations can be varied within wide limits. For example, the compositions comprise approximately 10 to 90 percent by weight of active substances, approximately 90 to 10 percent by weight of liquid or solid carriers and, if appropriate, up to 20 percent by weight of surfactants. The compositions can be applied in the customary manner, for example using water as carrier at rates of approximately 100 to 1000 liters of spray mixture per ha. Application of the compositions by the so-called low-volume and ultra-low-volume methods (ULV) is equally possible, as is their application in the form of granules and microgranuJes. These formulations can be prepared in a manner known per se. for example by grinding or mixing processes. If desired, preparations of the individual components can also be mixed only just before they are used, as is the case, for example, when preparing a tank mix under realistic conditions. The examples which follow are intended to illustrate the use of the compositions according to the invention. The synergistic effect was calculated as described by S.R. Colby in "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations" Weeds 15/1 (1967), pages 20 to 22. The following formula was used for this purpose: where X = herbicidal activity (%) when applying Substance A at p g/ha Y = herbicidal activity (%) when applying Substance B at q g/ha and E = herbicidal activity (%) to be expected when the application of Substances A + B at p + q g/ha amount to an additive effect. If the observed value exceeded the value E calculated using Colby's formula, the combination had a synergistic effect. Description of methods Square dishes with a side length of 13.5 cm and a height of 8.0 cm are filled with 900 ml of soil mixture. The following species are sown or planted in the dishes following a set routine: During the entire experimental period, the dishes remain in the greenhouse at a temperature between 25*C during the day and 20X during the night. The atmospheric humidity is between 60 and 80 %. During a 14-hour photo period, the plants receive at least 10,000 lux. Depending on the efficiency, the test substances are tested at three different concentrations. For the pre-emergence treatment, the test substances are applied to the sown plants by spraying in such a way that those dosages per hectare which are given in the tables result (converted). For post-emergence treatment, ECHCG, SCPJU, MOOVA and SAGPY are sown Into the first dish, and CYPDI and CYPSE and the pregerminated sown rice seeds are placed Into the second dish. After one day, the dishes are covered with transparent film to avoid desiccation. Three days prior to application, batches of three rice plants in the 2.5-leaf stage are planted in the second dish at a depth of 3 cm and 1 cm, respectively. Once Echinochloa crus-galli is in the 1.0-leaf stage, the active substance, or mixture, is applied. The water level is raised to 1-2 cm. The test substances are applied by pipetting onto a water surface area of approximately 170 cm2 so that the dosages per hectare which are given in the tables result (converted). Example 1 Mixtures of (A) with bifenox (B1) For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazoIylcarbonitriIe (A) was applied at rates of 12.5/25/50 g/ha and (B1) at rates of 50 /100 / 200 g/ha. Synergistic effects were observed with ECHCG (E), CYPSE, MOOVA and SCPJU, as can be seen from Table 1 below. Example 2 Mixtures of (A) with CH-900 (B2) For the experiment, 1-(3-chloro-4,5,6,7-tetrahyclropyrazolo-[1,5-a]-pyridin2-yI)-5-{methylpropargyIamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B2) at rates of 12.51251 SO g/ha. Synergistic effects were observed with ECHCG (E), SAGPY. SCPJU and CYPDI, as can be seen from Table 2 below. Example 3 Mixtures of (A) with MCPA (83) For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methyipropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B3) at rates of 50 /100 / 200 g/ha. Synergistic effects were observed with the two ECHCG species, CYPSE, SCPJU and CYPDI, as can be seen from Table 3 below. Example 4 Mixtures of (A) with nitrofen (B4) For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyricIin-2-yl)-5-methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B4) at rates of 25 / 50 / 200 g/ha. Synergistic effects were observed with ECHCG, SAGPY, SCPJU and CYPDI, as can be seen from Table 4 below. Example 5 Mixtures of (A) with oxadiazon (B5) For the experiment, 1-(3-chloro-4,5,6,7-tetrahyclropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B5) at rates of 125 / 250 / 500 g/ha. Synergistic effects were observed with ECHCG (E), CYPSE, SAGPY and SCPJU as can be seen from Table 5 below. Example 6 Mixtures of (A) with penclimethalin (B6) For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyra2olo-[1.5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyra2olylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B6) at rates of 50 /100 / 200 g/ha. Synergistic effects were observed with ECHCG (US), CYPSE, SAGPY and CYPDi as can be seen from Table 6 below. Example 7 Mixtures of (A) with simetryn (B7) For the experiment, 1-(3-chloro-4,5,6,7-tetrahyclropyrazolo-[1,5-a]-pyriclin-2-yl)-5-(methylpropargyiamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B7) at rates of 50 /100 / 200 g/ha. Synergistic effects were observed with CYPSE, SAGPY, SCPJU and CYPDI, as can be seen from Table 7 below. Example 8 Mixtures of (A) with sulcotrione (B8) For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-y[)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B8) at rates of 25 / 50 /100 g/ha. Synergistic effects were observed with the two ECHCG species, SAGPY, SCPJU and CYPDI, as can be seen from Table 8 below. Example 9 Mixtures of (A) with trifiuralin (B9) For the experiment, 1-(3-chloro-4,5,6,7-tetrahyclropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazDlylcarbonitrile (A) was applied at rates of 12.5 / 25 / 50 g/ha and (B9) at rates of 250 / 500 /1000 g/ha. Synergistic effects were observed with ECHCG (E), CYPSE. SAGPY and CYPDI, as can be seen from Table 9 below. Example 10 Mixtures of (A) with bentazone (B10) For the experiment, bentazone was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. A synergistic effect was found in the mixing ratios 25 g/ha of (A) + 250 / 500 /1000 g/ha of bentazone, as can be seen from Table 10 below. Example 11 Mixtures of (A) with molinate (B11) For the experiment, molinate was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. With the mixing ratios used, a synergistic effect was found for European and American Echinochloa crus-galii and for the Cyperus species CYPSE and CYPDI, where the proportion of (A) was lower than the proportion of component (B11), as can be seen from Tables 11A and 11B below. Example 12 Mixtures of (A) with dalmuron (B12) For the experiment, dalmuron was applied at rates of 200 / 400 / 800 g/ha and (A) at rates of 25 / 50 /100 g/ha. For a variety of mixing ratios, a synergistic effect was observed with ECHCG (E), for the Cyperus species CYPSE and CYPDI and for SAGPY, as can be seen from Tables 12A, 12B and 12C below. Example 13 Mixtures of (A) with thiobencarb (B13) For the experiment, thiobencarb was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with European Echinochloa crus-galli and for SAGPY, as shown in Table 13 below. Example 14 Mixtures of (A) with butachlor (B14) For the experiment, butachlor was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. For most mixing ratios, a synergistic effect was observed with SAGPY, as shown in Table 14 below. Example 15 Mixtures of (A) with pretilachlor (B15) For the experiment, pretilachlor was employed at rates of 200 / 400 / 600 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with SCPJU and CYPDI, as shown in Table 15 below. Example 16 Mixtures of (A) with dimepiperate For the experiment, dimepiperate was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with SAGPY and CYPDI, as shown in Table 16 below. Example 17 Mixtures of (A) with fenoxaprop-ethyl (B17) For the experiment, fenoxaprop-ethyl was applied at rates of 5 /10 / 20 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG(US) and CYPDI, as shown in Table 17 below. Example 18 Mixtures of (A) with clomeprop (618) For the experiment, clomeprop was applied at rates of 200 / 400 / 800 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with CYPDI, as shown in Table 18 below. Example 19 Mixtures of (A) with cinmethylin (B19) For the experiment, cinmethylin was applied at rates of 10 / 20 / 40 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG(European) and CYPDI, as shown in Table 19 below. Example 20 Mixtures of (A) with bromobutide (B20) For the experiment, bromobutide was applied at rates of 100 / 200 / 400 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG(European) and ECHCG (American), as shown in Table 20 below. Example 21 Mixtures of (A) with quinclorac (B21) For the experiment, quinclorac was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with CYPSE and SCPJU, as shown in Table 21 below. Example 22 Mixtures of (A) with mefenacet (B22) For the experiment, mefenacet was applied at rates of 250 / 500 /1000 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with SAGPY, as shown in Table 21 below. Example 23 Mixtures of (A) with pyrazosulforon-ethyl (B23) For the experiment, pyrazosulforon-ethyl was applied at rates of 10 / 40 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with CYPDI, as shown in Table 23 below. Example 24 Mixtures of (A) with esprocarb (B24) For the experiment, esprocarb was applied at rates of 200 / 4O0 / 800 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG (European) and SCPJU. as shown in Table 24 below. Example 25 Mixtures of (A) with cinosulfuron (B25) For the experiment, cinosulfuron was applied at rates of 25 / 75 g/ha and (A) at rates of 25/50/100 g/ha. For some mixing ratios, a synergistic effect was observed with CYPSE, as shown in Table 25 below. Example 25 Mixtures of (A) with thenylchlor (B26) For the experiment, thenylchlor was applied at rates of 25 / 50 / 75 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG (European), CYPSE and SAGPY. as shown in Tables 26A and 26b below. Example 27 Mixtures of (A) with cumyluron (B27) For the experiment, cumyluron was applied at rates of 25 / 50 / 75 g/ha and (A) at rates of 25 / 50 /100 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG (European) and ECHCG (American), as shown in Table 27 below. Example 28 Mixtures of (A) with MK 243 (B28) For the experiment, MK 243 was applied at rates of 25 / 50 / 75 g/ha and (A) at rates of 25/50/100 g/ha, MK 243 was present as a WP20 formulation, and (A) as a WP5 formulation. For some mixing ratios, a synergistic effect was found with CYPSE and CYDPI. as can be seen in Table 28 below. Example 29 Mixtures of (A) with naproanilide (B29) For the experiment, naproanilide was applied at rates of 500 / 625 / 750 g/ha and (A) at rates of 100 /125 /150 g/ha. For some mixing ratios, a synergistic effect was observed with CYPSE, as shown in Table 29 below. Example 30 Mixtures of (A) with anilofos (B30) For the experiment, anilofos was applied at rates of 62.5 / 93.8 /125 g/ha and (A) at rates of 50 / 75 /100 g/ha. For all mixing ratios tested, a synergistic effect was found with CYPSE, as can be seen in Table 30 below. Example 31 Mixtures of (A) with benfuresate (B31) For the experiment, benfuresate was applied at rates of 150 / 200 / 250 g/ha and (A) at rates of 50/75/100 g/ha. For some mixing ratios, a synergistic effect was observed with CYPDI, as shown in Table 31 below. Example 32 Mixtures of (A) with piperophos (B32) For the experiment, 1 -(3-chloro-4.5.6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 25 and 100 g/ha and piperophos at rates of 400 and 800 g/ha. For some mixing ratios, a synergistic effect was observed with SCP JU, as shown in table 32 below. Example 33 Mixtures of (A) with pyributicarb (B33) For the experiment. 1-(3-chlorO-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin"2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 25 and 50 g/ha and pyributicarb at rates of 200 and 400 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG. as shown in table 33 below. Example 34 Mixtures of (A) with ethoxysulfuron (B34) For the experiment, 1-(3-chloro-4.5,6,7-tetrahydropyra2olo-l1,5-a]-pyri(Jin-2-yl)-5-(methylpropargylamino)-4-pyrazoIylcarbonitr!le (A) was applied at rates of 12.5 / 25 / 50 g/ha and ethoxysulfuron at rates of 5, 10 and 20 g/ha. For several mixing ratios, a synergistic effect was observed with ECHCG (2.5 - leaf stage), as shown in table 34 below. Example 35 Mixtures of (A) with bensulfuronmelhyl For the experiment, 1-(3-chloro-4,5,6.7-tetrahyclropyrazolo-[1.5-a]-pyridin-2-yl)-5-(methylpropargylamino-4-pyrazoiylcarbonitrile (A) was applied at rates of 12.5 and 25 g/ha and bensulfuronmethyl at rates of 10 and 20 g/ha. A synergistic effect was observed with ECHCG (2.5 - leaf stage), as shown in table 35 below. Example 36 Mixtures of (A) with pyrazolate For the experiment. 1-(3-chloro-4.5.6.7-tetrahydropyra2olo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 50 and 100 g/ha and pyrazolate at rates of 500 and 1000 g/ha. For some mixing ratios, a synergistic effect was observed with PASDS, as shown in table 36 below. Example 37 Mixtures of (A) with pyrazoxyfen For the experiment. 1-(3-chloro-4.5.67-tetrahydropyrazolo-[1.5-a]-pyridin-2-yl)-5-(methylpropargyIamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 50 and 100 g/ha and pyrazoxyfen at rates of 500 and 1000 g/ha. For some mixing ratios, a synergistic effect was observed with PASDS, as shown in table 37 below. Example 38 Mixtures of (A) with benzofenap For the experiment, 1-{3-chloro-4,5.6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 50 g/ha and benzofenap at rates of 500 and 1000 g/ha. A synergistic effect was observed with ECHCG. as shown in table 38 below. Example 39 Mixtures of (A) with cyclosulfamuron For the experiment, 1-(3-chloro-4,5,6,7-tetrahydropyra2olo-[1,5-a]-pyridin-2"yl)-5-(methylpropargylamino)-4-pyra2olylcarbonitrile (A) was applied at rates of 6.25 and 12.5 g/ha and cyclosulfamuron at rates of 15 and 30 g/ha.. For some mixing ratios, a synergistic effect was observed with SCPJU, as shown in table 39 below. Example 40 Mixtures of (A) with cyhalofop-butyl For the experiment. 1-(3-chloro-4.5,67-tetrahydropyra20lo-[1,5-a]-pyndin-2-yl)-5-(methylpropargylamino)-4-pyra2olylcarbonitrile (A) was applied at rates of 25 and 50 g/ha and cyhalofop-butyl at rates of 15 and 30 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG. as shown in table 40 below. Example 41 Mixtures of (A) with NBA - 061 For the experiment. 1-(3-chloro-4,5,6,7-tetrahydropyra2olo-[1.5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 25 and 50 g/ha and NBA-051 at rates of 12.5 and 25 g/ha. For some mixing ratios, a synergistic effect was observed with ECHCG, as shown in table 41 below. Example 42 Mixtures of (A) with azimsulfuron For the experiment, 1-(3-chloro-4.5,5,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile (A) was applied at rates of 30 and 50 g/ha and azimsulfuron at rates of 5 and 10 g/ha. For some mixing ratios, a synergistic effect was observed with CYPSE, as shown in table 42 below. WE CLAIM: 1. A herbicidal composition having a synergestic effect of active components which comprises, as active components, a mixture of l-(3-chloro-4,5,6,7-tetrahydropyrazolo-[l,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)]. 2. The herbicidal composition as claimed in claim 1 wherein the weight ratio of components (A) and (B) in the mixture is between 1:0.1 and 1:100. 3. The herbicidal composition as claimed in claim 2 wherein the weight ratio is between 1:0.5 and 1:50, 4. The method of controlling weeds, which comprises treating the weeds with a composition as claimed in any of claims I to 3. 5. The method as claimed in claim 4 wherein the weeds are controlled in a crop. 6. The method as claimed in claim 5, wherein the crop is rice.

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